Unnamed: 0
int64 0
445k
| level_0
int64 0
1.94M
| index
float64 0
1.81M
⌀ | original_rxn
stringlengths 104
2.67k
| fragments
stringlengths 6
161
⌀ | source
stringlengths 11
26
| year
int64 1.98k
2.02k
| mapped_rxn
stringlengths 110
2.63k
| confidence
float64 0
1
| canonical_rxn_with_fragment_info
stringlengths 25
599
| canonical_rxn
stringlengths 25
599
| ID
stringlengths 17
32
| reaction_hash
stringlengths 56
56
| reactants
stringlengths 55
1.33k
| products
stringlengths 51
1.3k
| retro_template
stringlengths 46
417
| template_hash
stringclasses 1k
values | selectivity
float64 0
1
| outcomes
float64 1
15
| reagents
stringlengths 1
370
⌀ | labels
int64 0
999
|
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
161,836 | 571,424 | 952,457 | CC#N.C([O:6][P:7]([C:12]([CH3:16])([CH3:15])[CH2:13][NH2:14])(=[O:11])[O:8]CC)C.C[Si](Br)(C)C>CO>[NH2:14][CH2:13][C:12]([P:7](=[O:6])([OH:11])[OH:8])([CH3:16])[CH3:15] | null | US07649015B2_3925 | 2,010 | CC#N.CC[O:8][P:6]([C:2]([CH3:1])([CH3:3])[CH2:4][NH2:5])(=[O:7])[O:9]CC.CO.C[Si](C)(C)Br>>[CH3:1][C:2]([CH3:3])([CH2:4][NH2:5])[P:6](=[O:7])([OH:8])[OH:9] | 0.370711 | CC#N.CCOP(=O)(OCC)C(C)(C)CN.CO.C[Si](C)(C)Br>>CC(C)(CN)P(=O)(O)O | CC#N.CCOP(=O)(OCC)C(C)(C)CN.CO.C[Si](C)(C)Br>>CC(C)(CN)P(=O)(O)O | US07649015B2_3925grants | 1ef040200708469c6a527ed903745f4ecd62cb98094d4655fb63d12b | CC#N.CC[O:8][P:6]([C:2]([CH3:1])([CH3:3])[CH2:4][NH2:5])(=[O:7])[O:9]CC.CO.C[Si](C)(C)Br | [CH3:1][C:2]([CH3:3])([CH2:4][NH2:5])[P:6](=[O:7])([OH:8])[OH:9] | ([OH;D1;+0:1]-[#15:2]-[OH;D1;+0:3])>>(C-C-[O;H0;D2;+0:1]-[#15:2]-[O;H0;D2;+0:3]-C-C) | b4595a08df6970ad8eb8dfa2ee3a90217a7c5435a1c378de56a3d36c | 1 | 1 | CC#N.CO.C[Si](C)(C)Br | 535 |
308,040 | 1,001,468 | 1,693,391 | [CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[O:10])=[CH:5][CH:4]=1.C(N(CC)CC)C.Br[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]>C(#N)C.C([O-])(O)=O.[Na+]>[CH2:29]([O:28][C:26](=[O:27])[CH2:25][N:14]1[CH2:15][CH2:16][CH:11]([C:9](=[O:10])[C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[CH2:12][CH2:13]1)[CH3:30] | |f:4.5| | US09181266B2_0454 | 2,015 | Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].CC#N.CCN(CC)CC.O=C([O-])O.[NH:7]1[CH2:8][CH2:9][CH:10]([C:11](=[O:12])[c:13]2[cH:14][cH:15][c:16]([O:17][CH3:18])[cH:19][cH:20]2)[CH2:21][CH2:22]1.[Na+]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][N:7]1[CH2:8][CH2:9][CH:10]([C:11](=[O:12])[c:13]2[cH:14][cH:15][c:16]([O:17][CH3:18])[cH:19][cH:20]2)[CH2:21][CH2:22]1 | 0.851969 | CC#N.CCN(CC)CC.CCOC(=O)CBr.COc1ccc(C(=O)C2CCNCC2)cc1.O=C([O-])O~[Na+]>>CCOC(=O)CN1CCC(C(=O)c2ccc(OC)cc2)CC1 | CC#N.CCN(CC)CC.CCOC(=O)CBr.COc1ccc(C(=O)C2CCNCC2)cc1.O=C([O-])O.[Na+]>>CCOC(=O)CN1CCC(C(=O)c2ccc(OC)cc2)CC1 | US09181266B2_0454grants | 161cc88072c2680d15a55f1cbd76440b47086fcbb3286f81c766a614 | Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].CC#N.CCN(CC)CC.O=C([O-])O.[NH:7]1[CH2:8][CH2:9][CH:10]([C:11](=[O:12])[c:13]2[cH:14][cH:15][c:16]([O:17][CH3:18])[cH:19][cH:20]2)[CH2:21][CH2:22]1.[Na+] | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][N:7]1[CH2:8][CH2:9][CH:10]([C:11](=[O:12])[c:13]2[cH:14][cH:15][c:16]([O:17][CH3:18])[cH:19][cH:20]2)[CH2:21][CH2:22]1 | ([C:7]-[N;H0;D3;+0:8](-[C:9])-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5]-[C;D1;H3:6])>>(Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5]-[C;D1;H3:6]).([C:7]-[NH;D2;+0:8]-[C:9]) | ea9f8d80dccdcd80502d80ab51dc8f26cd63ed89bfafd6175b25064e | 1 | 1 | CC#N.CCN(CC)CC.O=C([O-])O.[Na+] | 467 |
413,427 | 1,685,723 | null | CC(O)=O.[CH3:5][C:6]1([CH:10]=O)[CH2:9][O:8][CH2:7]1.[NH2:12][C@@H:13]([C:19]1[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][CH:20]=1)[CH2:14][C:15]([O:17][CH3:18])=[O:16].C([BH3-])#N.[Na+]>CC#N>[CH3:18][O:17][C:15](=[O:16])[CH2:14][C@H:13]([C:19]1[CH:20]=[CH:21][C:22]([C:25]#[N:26])=[CH:23][CH:24]=1)[NH:12][CH2:10][C:6]1([CH3:5])[CH2:7][O:8][CH2:9]1 | |f:3.4| | US20150126492A1_0680 | 2,015 | CC#N.CC(=O)O.O=[CH:8][C:9]1([CH3:10])[CH2:11][O:12][CH2:13]1.[BH3-]C#N.[CH3:1][O:2][C:3](=[O:4])[CH2:5][C@@H:6]([NH2:7])[c:14]1[cH:15][cH:16][c:17]([C:18]#[N:19])[cH:20][cH:21]1.[Na+]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][C@@H:6]([NH:7][CH2:8][C:9]1([CH3:10])[CH2:11][O:12][CH2:13]1)[c:14]1[cH:15][cH:16][c:17]([C:18]#[N:19])[cH:20][cH:21]1 | 0.697562 | CC#N.CC(=O)O.CC1(C=O)COC1.COC(=O)C[C@@H](N)c1ccc(C#N)cc1.[BH3-]C#N~[Na+]>>COC(=O)C[C@@H](NCC1(C)COC1)c1ccc(C#N)cc1 | CC#N.CC(=O)O.CC1(C=O)COC1.COC(=O)C[C@@H](N)c1ccc(C#N)cc1.[BH3-]C#N.[Na+]>>COC(=O)C[C@@H](NCC1(C)COC1)c1ccc(C#N)cc1 | US20150126492A1_0680apps | c203d0498f3ce529858adb12cb7dcfab2d5e4cbb467424ef710b8de1 | CC#N.CC(=O)O.O=[CH:8][C:9]1([CH3:10])[CH2:11][O:12][CH2:13]1.[BH3-]C#N.[CH3:1][O:2][C:3](=[O:4])[CH2:5][C@@H:6]([NH2:7])[c:14]1[cH:15][cH:16][c:17]([C:18]#[N:19])[cH:20][cH:21]1.[Na+] | [CH3:1][O:2][C:3](=[O:4])[CH2:5][C@@H:6]([NH:7][CH2:8][C:9]1([CH3:10])[CH2:11][O:12][CH2:13]1)[c:14]1[cH:15][cH:16][c:17]([C:18]#[N:19])[cH:20][cH:21]1 | ([C:2]-[CH2;D2;+0:1]-[NH;D2;+0:3]-[C:4]-[c:5]1:[c:6]:[c:7]:[c:8]:[c:9]:[c:10]:1)>>(O=[CH;D2;+0:1]-[C:2]).([NH2;D1;+0:3]-[C:4]-[c:5]1:[c:6]:[c:7]:[c:8]:[c:9]:[c:10]:1) | 10f5d31feb519009d195681c5be1d3bfee7ccfc3c2d077ad45c1540d | 1 | 1 | CC#N.CC(=O)O.[BH3-]C#N.[Na+] | 627 |
174,888 | 610,959 | 1,012,541 | [F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[O:13][C:12]([C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH2:25][C:26]([O:28]C)=[O:27])=[CH:19][CH:18]=2)=[O:15])=[N:11][N:10]=1.CO.[OH-].[Na+].Cl>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[O:13][C:12]([C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[CH:19][CH:18]=2)=[O:15])=[N:11][N:10]=1 | |f:2.3| | US07795283B2_1637 | 2,010 | C1CCOC1.CO.C[O:3][C:2](=[O:1])[CH2:4][CH2:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([NH:11][C:12](=[O:13])[c:14]2[n:15][n:16][c:17]([NH:18][c:19]3[cH:20][cH:21][cH:22][cH:23][c:24]3[F:25])[o:26]2)[cH:27][cH:28]1.Cl.[Na+].[OH-]>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([NH:11][C:12](=[O:13])[c:14]2[n:15][n:16][c:17]([NH:18][c:19]3[cH:20][cH:21][cH:22][cH:23][c:24]3[F:25])[o:26]2)[cH:27][cH:28]1 | 0.88128 | C1CCOC1.CO.COC(=O)CCCc1ccc(NC(=O)c2nnc(Nc3ccccc3F)o2)cc1.Cl.[Na+]~[OH-]>>O=C(O)CCCc1ccc(NC(=O)c2nnc(Nc3ccccc3F)o2)cc1 | C1CCOC1.CO.COC(=O)CCCc1ccc(NC(=O)c2nnc(Nc3ccccc3F)o2)cc1.Cl.[Na+].[OH-]>>O=C(O)CCCc1ccc(NC(=O)c2nnc(Nc3ccccc3F)o2)cc1 | US07795283B2_1637grants | b4288f0e661e69a52c73ff45fa6e61ccf52a322777840171e66cffa2 | C1CCOC1.CO.C[O:3][C:2](=[O:1])[CH2:4][CH2:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([NH:11][C:12](=[O:13])[c:14]2[n:15][n:16][c:17]([NH:18][c:19]3[cH:20][cH:21][cH:22][cH:23][c:24]3[F:25])[o:26]2)[cH:27][cH:28]1.Cl.[Na+].[OH-] | [O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([NH:11][C:12](=[O:13])[c:14]2[n:15][n:16][c:17]([NH:18][c:19]3[cH:20][cH:21][cH:22][cH:23][c:24]3[F:25])[o:26]2)[cH:27][cH:28]1 | ([C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1])>>(C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]) | 0a02d2d47df007d05d29f7b852c5bfe9dcbd7a32224d027cc636bd27 | 1 | 1 | C1CCOC1.CO.Cl.[Na+].[OH-] | 88 |
420,767 | 1,765,824 | null | Br[C:2]1[CH:3]=[C:4]2[C:12]3=[C:13]([C:15]4[C:20]([N:11]3[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]2=3)=[CH:19][CH:18]=[CH:17][CH:16]=4)[CH:14]=1.BrC1C=C2C3C=CC=C4C5C=CC=CC=5N(C=34)C2=CC=1.[CH3:41][C:42]1([CH3:58])[C:46]([CH3:48])([CH3:47])[O:45][B:44]([B:44]2[O:45][C:46]([CH3:48])([CH3:47])[C:42]([CH3:58])([CH3:41])[O:43]2)[O:43]1.C([O-])(=O)C.[K+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[CH3:41][C:42]1([CH3:58])[C:46]([CH3:48])([CH3:47])[O:45][B:44]([C:2]2[CH:3]=[C:4]3[C:12]4=[C:13]([C:15]5[C:20]([N:11]4[C:10]4[CH:9]=[CH:8][CH:7]=[CH:6][C:5]3=4)=[CH:19][CH:18]=[CH:17][CH:16]=5)[CH:14]=2)[O:43]1 | |f:3.4,6.7.8.9.10,11.12.13| | US20150287933A1_0131 | 2,015 | Br[c:6]1[cH:7][c:8]2[c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[n:15]3[c:16]4[cH:17][cH:18][cH:19][cH:20][c:21]4[c:22]([cH:23]1)[c:24]23.Brc1ccc2c(c1)c1cccc3c4ccccc4n2c31.C1COCCO1.CC(=O)[O-].CC1(C)OB([B:5]2[O:4][C:2]([CH3:1])([CH3:3])[C:26]([CH3:27])([CH3:28])[O:25]2)OC1(C)C.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Fe+2].[K+].[Pd].[Pd].c1ccc(P(c2ccccc2)[c-]2cccc2)cc1.c1ccc(P(c2ccccc2)[c-]2cccc2)cc1>>[CH3:1][C:2]1([CH3:3])[O:4][B:5]([c:6]2[cH:7][c:8]3[c:9]4[cH:10][cH:11][cH:12][cH:13][c:14]4[n:15]4[c:16]5[cH:17][cH:18][cH:19][cH:20][c:21]5[c:22]([cH:23]2)[c:24]34)[O:25][C:26]1([CH3:27])[CH3:28] | 0.053926 | Brc1cc2c3ccccc3n3c4ccccc4c(c1)c23.Brc1ccc2c(c1)c1cccc3c4ccccc4n2c31.C1COCCO1.CC(=O)[O-]~[K+].CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1~O=C(/C=C/c1ccccc1)/C=C/c1ccccc1~O=C(/C=C/c1ccccc1)/C=C/c1ccccc1~[Pd]~[Pd].[Fe+2]~c1ccc(P(c2ccccc2)[c-]2cccc2)cc1~c1ccc(P(c2ccccc2)[c-]2cccc2)cc1>>CC1(C)OB(c2cc3c4ccccc4n4c5ccccc5c(c2)c34)OC1(C)C | Brc1cc2c3ccccc3n3c4ccccc4c(c1)c23.Brc1ccc2c(c1)c1cccc3c4ccccc4n2c31.C1COCCO1.CC(=O)[O-].CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Fe+2].[K+].[Pd].[Pd].c1ccc(P(c2ccccc2)[c-]2cccc2)cc1.c1ccc(P(c2ccccc2)[c-]2cccc2)cc1>>CC1(C)OB(c2cc3c4ccccc4n4c5ccccc5c(c2)c34)OC1(C)C | US20150287933A1_0131apps | afe0bedefc236a3f3e2f06932afaffbff5506ae5dce87e4318456ced | Br[c:6]1[cH:7][c:8]2[c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[n:15]3[c:16]4[cH:17][cH:18][cH:19][cH:20][c:21]4[c:22]([cH:23]1)[c:24]23.Brc1ccc2c(c1)c1cccc3c4ccccc4n2c31.C1COCCO1.CC(=O)[O-].CC1(C)OB([B:5]2[O:4][C:2]([CH3:1])([CH3:3])[C:26]([CH3:27])([CH3:28])[O:25]2)OC1(C)C.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Fe+2].[K+].[Pd].[Pd].c1ccc(P(c2ccccc2)[c-]2cccc2)cc1.c1ccc(P(c2ccccc2)[c-]2cccc2)cc1 | [CH3:1][C:2]1([CH3:3])[O:4][B:5]([c:6]2[cH:7][c:8]3[c:9]4[cH:10][cH:11][cH:12][cH:13][c:14]4[n:15]4[c:16]5[cH:17][cH:18][cH:19][cH:20][c:21]5[c:22]([cH:23]2)[c:24]34)[O:25][C:26]1([CH3:27])[CH3:28] | ([#8:5]-[B;H0;D3;+0:4](-[#8:6])-[c;H0;D3;+0:1](:[c:2]):[c:3])>>(Br-[c;H0;D3;+0:1](:[c:2]):[c:3]).(C-C1(-C)-O-B(-[B;H0;D3;+0:4](-[#8:5])-[#8:6])-O-C-1(-C)-C) | 809111b01e38b549ab34d8fc095aeb8c0540db06f3c41a247745e882 | 1 | 1 | Brc1ccc2c(c1)c1cccc3c4ccccc4n2c31.C1COCCO1.CC(=O)[O-].O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Fe+2].[K+].[Pd].[Pd].c1ccc(P(c2ccccc2)[c-]2cccc2)cc1.c1ccc(P(c2ccccc2)[c-]2cccc2)cc1 | 942 |
374,885 | 844,424 | null | C(N(CC)CC)C.Cl[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].[CH2:19]([O:26][C:27]1[CH:67]=[CH:66][C:30]([CH2:31][CH2:32][NH:33][CH2:34][CH2:35][N:36]([CH:60]2[CH2:65][CH2:64][CH2:63][CH2:62][CH2:61]2)[C:37](=[O:59])[CH2:38][CH2:39][N:40]([CH2:51][CH2:52][C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[C:41](=[O:50])[O:42][CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[CH:29][C:28]=1[N+:68]([O-:70])=[O:69])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>ClCCl>[CH2:19]([O:26][C:27]1[CH:67]=[CH:66][C:30]([CH2:31][CH2:32][N:33]([CH2:34][CH2:35][N:36]([CH:60]2[CH2:65][CH2:64][CH2:63][CH2:62][CH2:61]2)[C:37](=[O:59])[CH2:38][CH2:39][N:40]([C:41]([O:42][CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[O:50])[CH2:51][CH2:52][C:53]2[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=2)[C:9](=[O:10])[O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:29][C:28]=1[N+:68]([O-:70])=[O:69])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1 | null | US20100056508A1_0485 | 2,010 | CCN(CC)CC.ClCCl.Cl[C:39](=[O:40])[O:41][CH2:42][c:43]1[cH:44][cH:45][cH:46][cH:47][cH:48]1.[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[N:11]([CH2:12][CH2:13][C:14](=[O:15])[N:16]([CH2:17][CH2:18][NH:19][CH2:20][CH2:21][c:22]1[cH:23][cH:24][c:25]([O:26][CH2:27][c:28]2[cH:29][cH:30][cH:31][cH:32][cH:33]2)[c:34]([N+:35](=[O:36])[O-:37])[cH:38]1)[CH:49]1[CH2:50][CH2:51][CH2:52][CH2:53][CH2:54]1)[CH2:55][CH2:56][c:57]1[cH:58][cH:59][cH:60][cH:61][cH:62]1>>[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[N:11]([CH2:12][CH2:13][C:14](=[O:15])[N:16]([CH2:17][CH2:18][N:19]([CH2:20][CH2:21][c:22]1[cH:23][cH:24][c:25]([O:26][CH2:27][c:28]2[cH:29][cH:30][cH:31][cH:32][cH:33]2)[c:34]([N+:35](=[O:36])[O-:37])[cH:38]1)[C:39](=[O:40])[O:41][CH2:42][c:43]1[cH:44][cH:45][cH:46][cH:47][cH:48]1)[CH:49]1[CH2:50][CH2:51][CH2:52][CH2:53][CH2:54]1)[CH2:55][CH2:56][c:57]1[cH:58][cH:59][cH:60][cH:61][cH:62]1 | 0.583498 | CCN(CC)CC.ClCCl.O=C(Cl)OCc1ccccc1.O=C(OCc1ccccc1)N(CCC(=O)N(CCNCCc1ccc(OCc2ccccc2)c([N+](=O)[O-])c1)C1CCCCC1)CCc1ccccc1>>O=C(OCc1ccccc1)N(CCC(=O)N(CCN(CCc1ccc(OCc2ccccc2)c([N+](=O)[O-])c1)C(=O)OCc1ccccc1)C1CCCCC1)CCc1ccccc1 | CCN(CC)CC.ClCCl.O=C(Cl)OCc1ccccc1.O=C(OCc1ccccc1)N(CCC(=O)N(CCNCCc1ccc(OCc2ccccc2)c([N+](=O)[O-])c1)C1CCCCC1)CCc1ccccc1>>O=C(OCc1ccccc1)N(CCC(=O)N(CCN(CCc1ccc(OCc2ccccc2)c([N+](=O)[O-])c1)C(=O)OCc1ccccc1)C1CCCCC1)CCc1ccccc1 | US20100056508A1_0485apps | 84f0f1447be6b0f0d465939bf1cc4b1bc4aff30f4934db3b432cda59 | CCN(CC)CC.ClCCl.Cl[C:39](=[O:40])[O:41][CH2:42][c:43]1[cH:44][cH:45][cH:46][cH:47][cH:48]1.[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[N:11]([CH2:12][CH2:13][C:14](=[O:15])[N:16]([CH2:17][CH2:18][NH:19][CH2:20][CH2:21][c:22]1[cH:23][cH:24][c:25]([O:26][CH2:27][c:28]2[cH:29][cH:30][cH:31][cH:32][cH:33]2)[c:34]([N+:35](=[O:36])[O-:37])[cH:38]1)[CH:49]1[CH2:50][CH2:51][CH2:52][CH2:53][CH2:54]1)[CH2:55][CH2:56][c:57]1[cH:58][cH:59][cH:60][cH:61][cH:62]1 | [O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[N:11]([CH2:12][CH2:13][C:14](=[O:15])[N:16]([CH2:17][CH2:18][N:19]([CH2:20][CH2:21][c:22]1[cH:23][cH:24][c:25]([O:26][CH2:27][c:28]2[cH:29][cH:30][cH:31][cH:32][cH:33]2)[c:34]([N+:35](=[O:36])[O-:37])[cH:38]1)[C:39](=[O:40])[O:41][CH2:42][c:43]1[cH:44][cH:45][cH:46][cH:47][cH:48]1)[CH:49]1[CH2:50][CH2:51][CH2:52][CH2:53][CH2:54]1)[CH2:55][CH2:56][c:57]1[cH:58][cH:59][cH:60][cH:61][cH:62]1 | ([C:11]-[N;H0;D3;+0:12](-[C:13])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4]-[c:5]1:[c:6]:[c:7]:[c:8]:[c:9]:[c:10]:1)>>(Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4]-[c:5]1:[c:6]:[c:7]:[c:8]:[c:9]:[c:10]:1).([C:11]-[NH;D2;+0:12]-[C:13]) | a279567c4bb6b41971b2bc62440d9904ae1fb6210d80a103504244e4 | 1 | 2 | CCN(CC)CC.ClCCl | 427 |
357,988 | 596,214 | null | [CH2:1]([O:8][C:9]([N:11]1[CH:15]([C:16]([OH:18])=[O:17])[CH2:14][S:13][C@@H:12]1[CH:19]1[CH2:24][CH2:23][CH2:22][NH:21][CH2:20]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[C:34](OC(=O)C)(=[O:36])[CH3:35]>ClCCl>[CH2:1]([O:8][C:9]([N:11]1[CH:15]([C:16]([OH:18])=[O:17])[CH2:14][S:13][C@@H:12]1[CH:19]1[CH2:24][CH2:23][CH2:22][N:21]([C:34](=[O:36])[CH3:35])[CH2:20]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1 | null | US20080181866A1_0520 | 2,008 | CC(=O)O[C:2]([CH3:1])=[O:3].CCN(C(C)C)C(C)C.ClCCl.[NH:4]1[CH2:5][CH2:6][CH2:7][CH:8]([C@H:9]2[S:10][CH2:11][CH:12]([C:13](=[O:14])[OH:15])[N:16]2[C:17](=[O:18])[O:19][CH2:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[CH2:27]1>>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][CH2:7][CH:8]([C@H:9]2[S:10][CH2:11][CH:12]([C:13](=[O:14])[OH:15])[N:16]2[C:17](=[O:18])[O:19][CH2:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[CH2:27]1 | 0.48575 | CC(=O)OC(C)=O.CCN(C(C)C)C(C)C.ClCCl.O=C(O)C1CS[C@H](C2CCCNC2)N1C(=O)OCc1ccccc1>>CC(=O)N1CCCC([C@H]2SCC(C(=O)O)N2C(=O)OCc2ccccc2)C1 | CC(=O)OC(C)=O.CCN(C(C)C)C(C)C.ClCCl.O=C(O)C1CS[C@H](C2CCCNC2)N1C(=O)OCc1ccccc1>>CC(=O)N1CCCC([C@H]2SCC(C(=O)O)N2C(=O)OCc2ccccc2)C1 | US20080181866A1_0520apps | 4ce08cc360684a254630541655d2fa132066759b989546f83fafaa31 | CC(=O)O[C:2]([CH3:1])=[O:3].CCN(C(C)C)C(C)C.ClCCl.[NH:4]1[CH2:5][CH2:6][CH2:7][CH:8]([C@H:9]2[S:10][CH2:11][CH:12]([C:13](=[O:14])[OH:15])[N:16]2[C:17](=[O:18])[O:19][CH2:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[CH2:27]1 | [CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][CH2:7][CH:8]([C@H:9]2[S:10][CH2:11][CH:12]([C:13](=[O:14])[OH:15])[N:16]2[C:17](=[O:18])[O:19][CH2:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[CH2:27]1 | ([C:4]-[N;H0;D3;+0:5](-[C:6])-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])>>(C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3]).([C:4]-[NH;D2;+0:5]-[C:6]) | 850466ba28e440ccfbe243813dd37fe45c414b2a9ee742dafad2e7ee | 1 | 1 | CCN(C(C)C)C(C)C.ClCCl | 369 |
403,053 | 1,470,192 | null | [C:1](/[CH:3]=[CH:4]/[S:5]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2([C:20](O)=[O:21])[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[CH:10][CH:9]=1)(=[O:7])=[O:6])#[N:2].[CH:23]1([NH2:29])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>C(#N)C>[CH:23]1([NH:29][C:20]([C:14]2([C:11]3[CH:10]=[CH:9][C:8]([S:5](/[CH:4]=[CH:3]/[C:1]#[N:2])(=[O:7])=[O:6])=[CH:13][CH:12]=3)[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[O:21])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1 | |f:3.4| | US20140005175A1_0268 | 2,014 | CC#N.CCN=C=NCCCN(C)C.Cl.O[C:13]([C:12]1([c:11]2[cH:10][cH:9][c:8]([S:5](/[CH:4]=[CH:3]/[C:2]#[N:1])(=[O:6])=[O:7])[cH:28][cH:27]2)[CH2:22][CH2:23][O:24][CH2:25][CH2:26]1)=[O:14].On1nnc2ccccc21.[NH2:15][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1>>[N:1]#[C:2]/[CH:3]=[CH:4]/[S:5](=[O:6])(=[O:7])[c:8]1[cH:9][cH:10][c:11]([C:12]2([C:13](=[O:14])[NH:15][CH:16]3[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]3)[CH2:22][CH2:23][O:24][CH2:25][CH2:26]2)[cH:27][cH:28]1 | 0.468887 | CC#N.CCN=C=NCCCN(C)C~Cl.N#C/C=C/S(=O)(=O)c1ccc(C2(C(=O)O)CCOCC2)cc1.NC1CCCCC1.On1nnc2ccccc21>>N#C/C=C/S(=O)(=O)c1ccc(C2(C(=O)NC3CCCCC3)CCOCC2)cc1 | CC#N.CCN=C=NCCCN(C)C.Cl.N#C/C=C/S(=O)(=O)c1ccc(C2(C(=O)O)CCOCC2)cc1.NC1CCCCC1.On1nnc2ccccc21>>N#C/C=C/S(=O)(=O)c1ccc(C2(C(=O)NC3CCCCC3)CCOCC2)cc1 | US20140005175A1_0268apps | 3d49168d996bcc15d94764e7f7fbaac69217a5a72573630766b75678 | CC#N.CCN=C=NCCCN(C)C.Cl.O[C:13]([C:12]1([c:11]2[cH:10][cH:9][c:8]([S:5](/[CH:4]=[CH:3]/[C:2]#[N:1])(=[O:6])=[O:7])[cH:28][cH:27]2)[CH2:22][CH2:23][O:24][CH2:25][CH2:26]1)=[O:14].On1nnc2ccccc21.[NH2:15][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1 | [N:1]#[C:2]/[CH:3]=[CH:4]/[S:5](=[O:6])(=[O:7])[c:8]1[cH:9][cH:10][c:11]([C:12]2([C:13](=[O:14])[NH:15][CH:16]3[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]3)[CH2:22][CH2:23][O:24][CH2:25][CH2:26]2)[cH:27][cH:28]1 | ([C:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:5]-[C:4])>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([C:4]-[NH2;D1;+0:5]) | 9700dfbbea18932b10f40ed49527a6efd0b261364d0b5e3b1e240441 | 1 | 1 | CC#N.CCN=C=NCCCN(C)C.Cl.On1nnc2ccccc21 | 230 |
380,887 | 944,064 | null | C(O)(C(F)(F)F)=O.C(OC(=O)[N:14]([CH2:18][CH2:19][CH2:20][N:21]1[C:25]([NH2:26])=[C:24]([C:27](=[O:29])[NH2:28])[N:23]=[C:22]1[S:30][C:31]1[N:35]([CH:36]([CH3:38])[CH3:37])[C:34]2[CH:39]=[CH:40][CH:41]=[CH:42][C:33]=2[N:32]=1)[CH:15]([CH3:17])[CH3:16])(C)(C)C>C(Cl)Cl>[NH2:26][C:25]1[N:21]([CH2:20][CH2:19][CH2:18][NH:14][CH:15]([CH3:16])[CH3:17])[C:22]([S:30][C:31]2[N:35]([CH:36]([CH3:37])[CH3:38])[C:34]3[CH:39]=[CH:40][CH:41]=[CH:42][C:33]=3[N:32]=2)=[N:23][C:24]=1[C:27]([NH2:28])=[O:29] | null | US20100240656A1_0245 | 2,010 | CC(C)(C)OC(=O)[N:4]([CH:2]([CH3:1])[CH3:3])[CH2:5][CH2:6][CH2:7][n:8]1[c:9]([S:10][c:11]2[n:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[n:19]2[CH:20]([CH3:21])[CH3:22])[n:23][c:24]([C:25]([NH2:26])=[O:27])[c:28]1[NH2:29].ClCCl.O=C(O)C(F)(F)F>>[CH3:1][CH:2]([CH3:3])[NH:4][CH2:5][CH2:6][CH2:7][n:8]1[c:9]([S:10][c:11]2[n:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[n:19]2[CH:20]([CH3:21])[CH3:22])[n:23][c:24]([C:25]([NH2:26])=[O:27])[c:28]1[NH2:29] | 0.574101 | CC(C)N(CCCn1c(Sc2nc3ccccc3n2C(C)C)nc(C(N)=O)c1N)C(=O)OC(C)(C)C.ClCCl.O=C(O)C(F)(F)F>>CC(C)NCCCn1c(Sc2nc3ccccc3n2C(C)C)nc(C(N)=O)c1N | CC(C)N(CCCn1c(Sc2nc3ccccc3n2C(C)C)nc(C(N)=O)c1N)C(=O)OC(C)(C)C.ClCCl.O=C(O)C(F)(F)F>>CC(C)NCCCn1c(Sc2nc3ccccc3n2C(C)C)nc(C(N)=O)c1N | US20100240656A1_0245apps | 0c192b11ea39dbac00330d50288a062dc2650ad5aa7a71d4addd162d | CC(C)(C)OC(=O)[N:4]([CH:2]([CH3:1])[CH3:3])[CH2:5][CH2:6][CH2:7][n:8]1[c:9]([S:10][c:11]2[n:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[n:19]2[CH:20]([CH3:21])[CH3:22])[n:23][c:24]([C:25]([NH2:26])=[O:27])[c:28]1[NH2:29].ClCCl.O=C(O)C(F)(F)F | [CH3:1][CH:2]([CH3:3])[NH:4][CH2:5][CH2:6][CH2:7][n:8]1[c:9]([S:10][c:11]2[n:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[n:19]2[CH:20]([CH3:21])[CH3:22])[n:23][c:24]([C:25]([NH2:26])=[O:27])[c:28]1[NH2:29] | ([C:2]-[NH;D2;+0:1]-[C:3])>>(C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2])-[C:3]) | 55396c1492cc3823f0701ef923544f9f4c1af584b69f4ce5650dc5ae | 1 | 1 | ClCCl.O=C(O)C(F)(F)F | 575 |
214,590 | 723,014 | 1,190,036 | C[N:2](C)/[CH:3]=[CH:4]/[C:5]([C:7]1[C:12](=[O:13])[CH:11]=[CH:10][N:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:8]=1)=O.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=1[NH:29]N>>[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=1[N:29]1[C:5]([C:7]2[C:12](=[O:13])[CH:11]=[CH:10][N:9]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:8]=2)=[CH:4][CH:3]=[N:2]1 | null | US08178538B2_0556 | 2,012 | CN(C)/[CH:16]=[CH:15]/[C:14](=O)[c:13]1[c:2](=[O:1])[cH:3][cH:4][n:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[n:12]1.[NH2:17][NH:18][c:19]1[cH:20][c:21]([Cl:22])[cH:23][cH:24][c:25]1[Cl:26]>>[O:1]=[c:2]1[cH:3][cH:4][n:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[n:12][c:13]1-[c:14]1[cH:15][cH:16][n:17][n:18]1-[c:19]1[cH:20][c:21]([Cl:22])[cH:23][cH:24][c:25]1[Cl:26] | 0.859565 | CN(C)/C=C/C(=O)c1nn(-c2ccccc2)ccc1=O.NNc1cc(Cl)ccc1Cl>>O=c1ccn(-c2ccccc2)nc1-c1ccnn1-c1cc(Cl)ccc1Cl | CN(C)/C=C/C(=O)c1nn(-c2ccccc2)ccc1=O.NNc1cc(Cl)ccc1Cl>>O=c1ccn(-c2ccccc2)nc1-c1ccnn1-c1cc(Cl)ccc1Cl | US08178538B2_0556grants | 51229be3ac1c63f4b81b80ef4111549d4f99780ca5931a1bb1075aad | CN(C)/[CH:16]=[CH:15]/[C:14](=O)[c:13]1[c:2](=[O:1])[cH:3][cH:4][n:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[n:12]1.[NH2:17][NH:18][c:19]1[cH:20][c:21]([Cl:22])[cH:23][cH:24][c:25]1[Cl:26] | [O:1]=[c:2]1[cH:3][cH:4][n:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[n:12][c:13]1-[c:14]1[cH:15][cH:16][n:17][n:18]1-[c:19]1[cH:20][c:21]([Cl:22])[cH:23][cH:24][c:25]1[Cl:26] | ([#7;a:7]:[#7;a:6]:[c;H0;D3;+0:4](:[c:5])-[c;H0;D3;+0:3]1:[cH;D2;+0:2]:[cH;D2;+0:1]:[n;H0;D2;+0:8]:[n;H0;D3;+0:9]:1-[c;H0;D3;+0:10](:[c:11]):[c:12])>>(C-N(-C)/[CH;D2;+0:1]=[CH;D2;+0:2]/[C;H0;D3;+0:3](=O)-[c;H0;D3;+0:4](:[c:5]):[#7;a:6]:[#7;a:7]).([NH2;D1;+0:8]-[NH;D2;+0:9]-[c;H0;D3;+0:10](:[c:11]):[c:12]) | 37d83614e0c1d1adf7a0525755c7cc00bb5556369688bac2547dfa70 | 1 | 1 | null | 984 |
122,549 | 453,031 | 768,581 | C(OC(=O)[NH:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH:13]([C:17]2[N:28]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[C:36]#[N:37])[C:20]3[C:21](=[O:27])[N:22]([CH2:25][CH3:26])[CH:23]=[CH:24][C:19]=3[N:18]=2)[CH2:12]1)C1C=CC=CC=1>[Pd].CCO.C1COCC1>[NH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH:13]([C:17]2[N:28]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[C:36]#[N:37])[C:20]3[C:21](=[O:27])[N:22]([CH2:25][CH3:26])[CH:23]=[CH:24][C:19]=3[N:18]=2)[CH2:12]1 | |f:2.3| | US07169926B1_0618 | 2,007 | C1CCOC1.CCO.O=C(OCc1ccccc1)[NH:14][CH:13]1[CH2:12][CH2:11][CH2:10][CH:9]([c:8]2[n:7][c:6]3[cH:5][cH:4][n:3]([CH2:2][CH3:1])[c:27](=[O:28])[c:26]3[n:16]2[CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]2[C:24]#[N:25])[CH2:15]1.[Pd]>>[CH3:1][CH2:2][n:3]1[cH:4][cH:5][c:6]2[n:7][c:8]([CH:9]3[CH2:10][CH2:11][CH2:12][CH:13]([NH2:14])[CH2:15]3)[n:16]([CH2:17][c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]3[C:24]#[N:25])[c:26]2[c:27]1=[O:28] | 0.987163 | C1CCOC1~CCO.CCn1ccc2nc(C3CCCC(NC(=O)OCc4ccccc4)C3)n(Cc3ccccc3C#N)c2c1=O.[Pd]>>CCn1ccc2nc(C3CCCC(N)C3)n(Cc3ccccc3C#N)c2c1=O | C1CCOC1.CCO.CCn1ccc2nc(C3CCCC(NC(=O)OCc4ccccc4)C3)n(Cc3ccccc3C#N)c2c1=O.[Pd]>>CCn1ccc2nc(C3CCCC(N)C3)n(Cc3ccccc3C#N)c2c1=O | US07169926B1_0618grants | 2ae94fcc936e8a0d5369e67a294592d4d0ebd9634fbc9f99837e092b | C1CCOC1.CCO.O=C(OCc1ccccc1)[NH:14][CH:13]1[CH2:12][CH2:11][CH2:10][CH:9]([c:8]2[n:7][c:6]3[cH:5][cH:4][n:3]([CH2:2][CH3:1])[c:27](=[O:28])[c:26]3[n:16]2[CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]2[C:24]#[N:25])[CH2:15]1.[Pd] | [CH3:1][CH2:2][n:3]1[cH:4][cH:5][c:6]2[n:7][c:8]([CH:9]3[CH2:10][CH2:11][CH2:12][CH:13]([NH2:14])[CH2:15]3)[n:16]([CH2:17][c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]3[C:24]#[N:25])[c:26]2[c:27]1=[O:28] | ([C:2]-[NH2;D1;+0:1])>>(O=C(-O-C-c1:c:c:c:c:c:1)-[NH;D2;+0:1]-[C:2]) | 41e20f607b9e9b89cd4fe1c124c0263ca345e5973e1fadb9fde6fefb | 1 | 1 | C1CCOC1.CCO.[Pd] | 574 |
209,985 | 710,413 | 1,170,542 | [NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:3][CH2:2]1.[F:15][C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1.C(N(CC)CC)C>O1CCCC1>[F:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([N:1]2[CH2:2][CH2:3][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])[CH2:5][CH2:6]2)(=[O:24])=[O:23])=[CH:18][CH:17]=1 | null | US08148361B2_0217 | 2,012 | C1CCOC1.CCN(CC)CC.Cl[S:13](=[O:14])(=[O:15])[c:16]1[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH:9]1[CH2:10][CH2:11][NH:12][CH2:23][CH2:24]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH:9]1[CH2:10][CH2:11][N:12]([S:13](=[O:14])(=[O:15])[c:16]2[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]2)[CH2:23][CH2:24]1 | 0.271473 | C1CCOC1.CC(C)(C)OC(=O)NC1CCNCC1.CCN(CC)CC.O=S(=O)(Cl)c1ccc(F)cc1>>CC(C)(C)OC(=O)NC1CCN(S(=O)(=O)c2ccc(F)cc2)CC1 | C1CCOC1.CC(C)(C)OC(=O)NC1CCNCC1.CCN(CC)CC.O=S(=O)(Cl)c1ccc(F)cc1>>CC(C)(C)OC(=O)NC1CCN(S(=O)(=O)c2ccc(F)cc2)CC1 | US08148361B2_0217grants | ba995e381330865209d700e31be9bfd7adca7e61053c421476bf8ac6 | C1CCOC1.CCN(CC)CC.Cl[S:13](=[O:14])(=[O:15])[c:16]1[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH:9]1[CH2:10][CH2:11][NH:12][CH2:23][CH2:24]1 | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH:9]1[CH2:10][CH2:11][N:12]([S:13](=[O:14])(=[O:15])[c:16]2[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]2)[CH2:23][CH2:24]1 | ([C:5]-[N;H0;D3;+0:6](-[C:7])-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4])>>(Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4]).([C:5]-[NH;D2;+0:6]-[C:7]) | 1c3a913f221c79d5ab4e40f13ae7431f2711f9942a72ad3fc8bf5434 | 1 | 1 | C1CCOC1.CCN(CC)CC | 99 |
22,234 | 105,962 | 171,377 | [CH3:1][C:2]1([CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH:18]3[S:22][C:21](=[O:23])[NH:20][C:19]3=[O:24])=[CH:13][CH:12]=2)[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=O.C([O-])(=O)C.[Na+].Cl.[CH3:31][O:32][NH2:33]>C(O)C>[CH3:1][C:2]1([CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH:18]3[S:22][C:21](=[O:23])[NH:20][C:19]3=[O:24])=[CH:13][CH:12]=2)[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=[N:33][O:32][CH3:31] | |f:1.2,3.4| | US04728739_ | 1,988 | CC(=O)[O-].CCO.Cl.O=[C:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C:9]1([CH3:10])[CH2:11][O:12][c:13]1[cH:14][cH:15][c:16]([CH2:17][CH:18]2[S:19][C:20](=[O:21])[NH:22][C:23]2=[O:24])[cH:25][cH:26]1.[CH3:1][O:2][NH2:3].[Na+]>>[CH3:1][O:2][N:3]=[C:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C:9]1([CH3:10])[CH2:11][O:12][c:13]1[cH:14][cH:15][c:16]([CH2:17][CH:18]2[S:19][C:20](=[O:21])[NH:22][C:23]2=[O:24])[cH:25][cH:26]1 | 0.957099 | CC(=O)[O-]~[Na+].CC1(COc2ccc(CC3SC(=O)NC3=O)cc2)CCCCC1=O.CCO.CON~Cl>>CON=C1CCCCC1(C)COc1ccc(CC2SC(=O)NC2=O)cc1 | CC(=O)[O-].CC1(COc2ccc(CC3SC(=O)NC3=O)cc2)CCCCC1=O.CCO.CON.Cl.[Na+]>>CON=C1CCCCC1(C)COc1ccc(CC2SC(=O)NC2=O)cc1 | US04728739_grants | cb5b2f0a5dd2d6ab15d199a36b23eed53640213e2dd62db4c326c779 | CC(=O)[O-].CCO.Cl.O=[C:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C:9]1([CH3:10])[CH2:11][O:12][c:13]1[cH:14][cH:15][c:16]([CH2:17][CH:18]2[S:19][C:20](=[O:21])[NH:22][C:23]2=[O:24])[cH:25][cH:26]1.[CH3:1][O:2][NH2:3].[Na+] | [CH3:1][O:2][N:3]=[C:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C:9]1([CH3:10])[CH2:11][O:12][c:13]1[cH:14][cH:15][c:16]([CH2:17][CH:18]2[S:19][C:20](=[O:21])[NH:22][C:23]2=[O:24])[cH:25][cH:26]1 | ([#8:4]-[N;H0;D2;+0:5]=[C;H0;D3;+0:1](-[C:2])-[C:3])>>(O=[C;H0;D3;+0:1](-[C:2])-[C:3]).([#8:4]-[NH2;D1;+0:5]) | 7abd166054b33d08eaac11fe7b0162caf09599bf51bcbf598d37f286 | 1 | 1 | CC(=O)[O-].CCO.Cl.[Na+] | 86 |
363,871 | 667,567 | null | [Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[C:9]([O:13][C:14](O[C:14]([O:13][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:15])=[O:15])([CH3:12])([CH3:11])[CH3:10].C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C(Cl)Cl.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH:5][C:14]([O:13][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:15] | null | US20090042973A1_0321 | 2,009 | CC(C)(C)OC(=O)O[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].CCN(CC)CC.CCOC(C)=O.CN(C)c1ccncc1.ClCCl.[NH2:8][c:9]1[cH:10][cH:11][cH:12][c:13]([Br:14])[cH:15]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][cH:11][cH:12][c:13]([Br:14])[cH:15]1 | 0.213835 | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.CCN(CC)CC.CCOC(C)=O.CN(C)c1ccncc1.ClCCl.Nc1cccc(Br)c1>>CC(C)(C)OC(=O)Nc1cccc(Br)c1 | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.CCN(CC)CC.CCOC(C)=O.CN(C)c1ccncc1.ClCCl.Nc1cccc(Br)c1>>CC(C)(C)OC(=O)Nc1cccc(Br)c1 | US20090042973A1_0321apps | 50f17dfb0c7acd06806fd0043fd26cb16c018cb6f99de52e64426838 | CC(C)(C)OC(=O)O[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].CCN(CC)CC.CCOC(C)=O.CN(C)c1ccncc1.ClCCl.[NH2:8][c:9]1[cH:10][cH:11][cH:12][c:13]([Br:14])[cH:15]1 | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][cH:11][cH:12][c:13]([Br:14])[cH:15]1 | ([C;D1;H3:5]-[C:4](-[C;D1;H3:6])(-[C;D1;H3:7])-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[c:9])>>(C-C(-C)(-C)-O-C(=O)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7]).([NH2;D1;+0:8]-[c:9]) | dfd4a94a902e3babedba1e504ef44185b3b9e2bdf52136b6341cb77f | 1 | 1 | CCN(CC)CC.CCOC(C)=O.CN(C)c1ccncc1.ClCCl | 735 |
363,312 | 663,562 | null | Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([CH3:9])[N:3]=1.[CH3:10][NH2:11].C([O-])(O)=O.[Na+]>C1COCC1.C(Cl)(Cl)Cl>[Cl:8][C:6]1[N:5]=[C:4]([CH3:9])[N:3]=[C:2]([NH:11][CH3:10])[CH:7]=1 | |f:2.3| | US20090036448A1_1770 | 2,009 | C1CCOC1.ClC(Cl)Cl.Cl[c:3]1[cH:4][c:5]([Cl:6])[n:7][c:8]([CH3:9])[n:10]1.O=C([O-])O.[CH3:1][NH2:2].[Na+]>>[CH3:1][NH:2][c:3]1[cH:4][c:5]([Cl:6])[n:7][c:8]([CH3:9])[n:10]1 | 0.654087 | C1CCOC1.CN.Cc1nc(Cl)cc(Cl)n1.ClC(Cl)Cl.O=C([O-])O~[Na+]>>CNc1cc(Cl)nc(C)n1 | C1CCOC1.CN.Cc1nc(Cl)cc(Cl)n1.ClC(Cl)Cl.O=C([O-])O.[Na+]>>CNc1cc(Cl)nc(C)n1 | US20090036448A1_1770apps | 5cad77ff8cd35255aaab0b5ec0d0d9d5c8a95a6c32a559de6a30b431 | C1CCOC1.ClC(Cl)Cl.Cl[c:3]1[cH:4][c:5]([Cl:6])[n:7][c:8]([CH3:9])[n:10]1.O=C([O-])O.[CH3:1][NH2:2].[Na+] | [CH3:1][NH:2][c:3]1[cH:4][c:5]([Cl:6])[n:7][c:8]([CH3:9])[n:10]1 | ([C;D1;H3:7]-[NH;D2;+0:8]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1)>>(Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1).([C;D1;H3:7]-[NH2;D1;+0:8]) | 9ba15a7b9393a64a7fde93acd4e7b07a21f5e92fd01af7815d1917a2 | 1 | 1 | C1CCOC1.ClC(Cl)Cl.O=C([O-])O.[Na+] | 166 |
414,409 | 1,699,548 | null | [NH:1]([C:3]1[N:8]=[N:7][CH:6]=[C:5]([N:9]2[CH2:14][CH2:13][CH:12]([C:15]3[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=3[C:17]#[N:18])[CH2:11][CH2:10]2)[C:4]=1[C:23]([F:26])([F:25])[F:24])[NH2:2].[CH:27]1([CH2:30][C:31](Cl)=[O:32])[CH2:29][CH2:28]1>C(OCC)(=O)C.C1COCC1.C(=O)(O)[O-].[Na+]>[C:17]([C:16]1[CH:19]=[CH:20][CH:21]=[CH:22][C:15]=1[CH:12]1[CH2:13][CH2:14][N:9]([C:5]2[C:4]([C:23]([F:26])([F:25])[F:24])=[C:3]([NH:1][NH:2][C:31](=[O:32])[CH2:30][CH:27]3[CH2:29][CH2:28]3)[N:8]=[N:7][CH:6]=2)[CH2:10][CH2:11]1)#[N:18] | |f:4.5| | US20150152113A1_0277 | 2,015 | C1CCOC1.CCOC(C)=O.Cl[C:20](=[O:21])[CH2:22][CH:23]1[CH2:24][CH2:25]1.O=C([O-])O.[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH:9]1[CH2:10][CH2:11][N:12]([c:13]2[cH:14][n:15][n:16][c:17]([NH:18][NH2:19])[c:26]2[C:27]([F:28])([F:29])[F:30])[CH2:31][CH2:32]1.[Na+]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH:9]1[CH2:10][CH2:11][N:12]([c:13]2[cH:14][n:15][n:16][c:17]([NH:18][NH:19][C:20](=[O:21])[CH2:22][CH:23]3[CH2:24][CH2:25]3)[c:26]2[C:27]([F:28])([F:29])[F:30])[CH2:31][CH2:32]1 | 0.383505 | C1CCOC1.CCOC(C)=O.N#Cc1ccccc1C1CCN(c2cnnc(NN)c2C(F)(F)F)CC1.O=C(Cl)CC1CC1.O=C([O-])O~[Na+]>>N#Cc1ccccc1C1CCN(c2cnnc(NNC(=O)CC3CC3)c2C(F)(F)F)CC1 | C1CCOC1.CCOC(C)=O.N#Cc1ccccc1C1CCN(c2cnnc(NN)c2C(F)(F)F)CC1.O=C(Cl)CC1CC1.O=C([O-])O.[Na+]>>N#Cc1ccccc1C1CCN(c2cnnc(NNC(=O)CC3CC3)c2C(F)(F)F)CC1 | US20150152113A1_0277apps | 8b58ddeed5cff6dee403945d1cf7302043bc2d469875119b24179155 | C1CCOC1.CCOC(C)=O.Cl[C:20](=[O:21])[CH2:22][CH:23]1[CH2:24][CH2:25]1.O=C([O-])O.[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH:9]1[CH2:10][CH2:11][N:12]([c:13]2[cH:14][n:15][n:16][c:17]([NH:18][NH2:19])[c:26]2[C:27]([F:28])([F:29])[F:30])[CH2:31][CH2:32]1.[Na+] | [N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH:9]1[CH2:10][CH2:11][N:12]([c:13]2[cH:14][n:15][n:16][c:17]([NH:18][NH:19][C:20](=[O:21])[CH2:22][CH:23]3[CH2:24][CH2:25]3)[c:26]2[C:27]([F:28])([F:29])[F:30])[CH2:31][CH2:32]1 | ([#7:4]-[NH;D2;+0:5]-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3])>>(Cl-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([#7:4]-[NH2;D1;+0:5]) | 1ee1f445b33d6fc30e4e598011996da4b2a7bc05e9c3daf9b738b904 | 1 | 1 | C1CCOC1.CCOC(C)=O.O=C([O-])O.[Na+] | 450 |
155,688 | 553,551 | 925,687 | [F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.FC1C=CC(N2CCNCC2)=CC=1.[CH:30]1([CH2:33][CH2:34][NH:35][C:36]([C:38]2[N:39]=[N:40][C:41](Cl)=[CH:42][CH:43]=2)=[O:37])[CH2:32][CH2:31]1>>[CH:30]1([CH2:33][CH2:34][NH:35][C:36]([C:38]2[N:39]=[N:40][C:41]([N:12]3[CH2:13][CH2:14][N:9]([C:5]4[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:15])[F:16])[CH:4]=4)[CH2:10][CH2:11]3)=[CH:42][CH:43]=2)=[O:37])[CH2:32][CH2:31]1 | null | US07592343B2_0271 | 2,009 | Cl[c:12]1[cH:11][cH:10][c:9]([C:2](=[O:1])[NH:3][CH2:4][CH2:5][CH:6]2[CH2:7][CH2:8]2)[n:30][n:29]1.Fc1ccc(N2CCNCC2)cc1.[NH:13]1[CH2:14][CH2:15][N:16]([c:17]2[cH:18][cH:19][cH:20][c:21]([C:22]([F:23])([F:24])[F:25])[cH:26]2)[CH2:27][CH2:28]1>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][CH:6]1[CH2:7][CH2:8]1)[c:9]1[cH:10][cH:11][c:12]([N:13]2[CH2:14][CH2:15][N:16]([c:17]3[cH:18][cH:19][cH:20][c:21]([C:22]([F:23])([F:24])[F:25])[cH:26]3)[CH2:27][CH2:28]2)[n:29][n:30]1 | 0.199747 | FC(F)(F)c1cccc(N2CCNCC2)c1.Fc1ccc(N2CCNCC2)cc1.O=C(NCCC1CC1)c1ccc(Cl)nn1>>O=C(NCCC1CC1)c1ccc(N2CCN(c3cccc(C(F)(F)F)c3)CC2)nn1 | FC(F)(F)c1cccc(N2CCNCC2)c1.Fc1ccc(N2CCNCC2)cc1.O=C(NCCC1CC1)c1ccc(Cl)nn1>>O=C(NCCC1CC1)c1ccc(N2CCN(c3cccc(C(F)(F)F)c3)CC2)nn1 | US07592343B2_0271grants | 17248cc57114ce64893698b999d5f33e7275fdee572d317a386e7312 | Cl[c:12]1[cH:11][cH:10][c:9]([C:2](=[O:1])[NH:3][CH2:4][CH2:5][CH:6]2[CH2:7][CH2:8]2)[n:30][n:29]1.Fc1ccc(N2CCNCC2)cc1.[NH:13]1[CH2:14][CH2:15][N:16]([c:17]2[cH:18][cH:19][cH:20][c:21]([C:22]([F:23])([F:24])[F:25])[cH:26]2)[CH2:27][CH2:28]1 | [O:1]=[C:2]([NH:3][CH2:4][CH2:5][CH:6]1[CH2:7][CH2:8]1)[c:9]1[cH:10][cH:11][c:12]([N:13]2[CH2:14][CH2:15][N:16]([c:17]3[cH:18][cH:19][cH:20][c:21]([C:22]([F:23])([F:24])[F:25])[cH:26]3)[CH2:27][CH2:28]2)[n:29][n:30]1 | ([#7;a:4]:[#7;a:3]:[c;H0;D3;+0:1](:[c:2])-[N;H0;D3;+0:6](-[C:5])-[C:7])>>(Cl-[c;H0;D3;+0:1](:[c:2]):[#7;a:3]:[#7;a:4]).([C:5]-[NH;D2;+0:6]-[C:7]) | 985a0b0463f88646e6a35c0ff595cbd75ebed1b523deff0ac5075e82 | 1 | 1 | Fc1ccc(N2CCNCC2)cc1 | 406 |
12,705 | 63,539 | 104,023 | [C:1]([OH:16])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[CH3:17][C:18]1[CH:24]=[C:23]([OH:25])[CH:22]=[CH:21][C:19]=1[OH:20].B(F)(F)F.C(=O)([O-])[O-].[Na+].[Na+]>O>[CH3:17][C:18]1[CH:24]=[C:23]([C:22]([C:1](=[O:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[CH:21][C:19]=1[OH:20])[OH:25] | |f:3.4.5| | US04371604_ | 1,983 | FB(F)F.O.O=C([O-])[O-].O[C:14]([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:15].[Na+].[Na+].[cH:16]1[cH:17][c:18]([OH:19])[c:20]([CH3:21])[cH:22][c:23]1[OH:24]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14](=[O:15])[c:16]1[cH:17][c:18]([OH:19])[c:20]([CH3:21])[cH:22][c:23]1[OH:24] | 0.556398 | CCCCCCCCCCCCCC(=O)O.Cc1cc(O)ccc1O.FB(F)F.O.O=C([O-])[O-]~[Na+]~[Na+]>>CCCCCCCCCCCCCC(=O)c1cc(O)c(C)cc1O | CCCCCCCCCCCCCC(=O)O.Cc1cc(O)ccc1O.FB(F)F.O.O=C([O-])[O-].[Na+].[Na+]>>CCCCCCCCCCCCCC(=O)c1cc(O)c(C)cc1O | US04371604_grants | 009720e757dded849ac101ecfefc6e32d02aff3f8365993995c5c272 | FB(F)F.O.O=C([O-])[O-].O[C:14]([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:15].[Na+].[Na+].[cH:16]1[cH:17][c:18]([OH:19])[c:20]([CH3:21])[cH:22][c:23]1[OH:24] | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14](=[O:15])[c:16]1[cH:17][c:18]([OH:19])[c:20]([CH3:21])[cH:22][c:23]1[OH:24] | ([C:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[c;H0;D3;+0:5](:[c:4]):[c:6])>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([c:4]:[cH;D2;+0:5]:[c:6]) | 6b61173e5c75ff6409a7862fd7eb803f9aa0b57b0e9b8cc2cf6a75dd | 1 | 1 | FB(F)F.O.O=C([O-])[O-].[Na+].[Na+] | 435 |
172,987 | 605,232 | 1,003,288 | C([O:8][C:9](=[O:24])[CH2:10][O:11][P:12]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])C1C=CC=CC=1.[H][H]>CO.[Pd]>[C:20]([O:19][P:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])([O:11][CH2:10][C:9]([OH:24])=[O:8])=[O:13])([CH3:22])([CH3:23])[CH3:21] | null | US07776855B2_0109 | 2,010 | CO.[H][H].[Pd].c1ccc(C[O:12][C:10]([CH2:9][O:8][P:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])(=[O:7])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:11])cc1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][P:6](=[O:7])([O:8][CH2:9][C:10](=[O:11])[OH:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17] | 0.233366 | CC(C)(C)OP(=O)(OCC(=O)OCc1ccccc1)OC(C)(C)C.CO.[H][H].[Pd]>>CC(C)(C)OP(=O)(OCC(=O)O)OC(C)(C)C | CC(C)(C)OP(=O)(OCC(=O)OCc1ccccc1)OC(C)(C)C.CO.[H][H].[Pd]>>CC(C)(C)OP(=O)(OCC(=O)O)OC(C)(C)C | US07776855B2_0109grants | 0f44d3c5c2de30493df75e7f31b52d3762473117da41a42e830b2d19 | CO.[H][H].[Pd].c1ccc(C[O:12][C:10]([CH2:9][O:8][P:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])(=[O:7])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:11])cc1 | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][P:6](=[O:7])([O:8][CH2:9][C:10](=[O:11])[OH:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17] | ([C:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4])>>([C:1]-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-C-c1:c:c:c:c:c:1) | 3358e9d74bcf91ba7e96568094da103c2e3a143a7d89e0937034db20 | 1 | 1 | CO.[H][H].[Pd] | 186 |
61,049 | 258,227 | 436,949 | [F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[CH2:5][CH2:6]O.C(Br)(Br)(Br)[Br:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[CH2:5][CH2:6][Br:12] | null | US05889008_ | 1,999 | BrC(Br)(Br)[Br:9].ClCCl.O[CH2:8][CH2:7][c:6]1[cH:5][cH:4][cH:3][c:2]([F:1])[cH:10]1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][CH2:8][Br:9])[cH:10]1 | 0.257367 | BrC(Br)(Br)Br.ClCCl.OCCc1cccc(F)c1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>Fc1cccc(CCBr)c1 | BrC(Br)(Br)Br.ClCCl.OCCc1cccc(F)c1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>Fc1cccc(CCBr)c1 | US05889008_grants | cffbfda9c6b0c974cbe91b821fd51433c289d24101ded5f18fc0ae17 | BrC(Br)(Br)[Br:9].ClCCl.O[CH2:8][CH2:7][c:6]1[cH:5][cH:4][cH:3][c:2]([F:1])[cH:10]1.c1ccc(P(c2ccccc2)c2ccccc2)cc1 | [F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][CH2:8][Br:9])[cH:10]1 | ([Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3])>>(Br-C(-Br)(-Br)-[Br;H0;D1;+0:1]).(O-[CH2;D2;+0:2]-[C:3]) | 9bf4542b6ebf1b0dbc776e9c158fdb37e9984a15e06ba7fbdad968ad | 1 | 1 | ClCCl.c1ccc(P(c2ccccc2)c2ccccc2)cc1 | 378 |
173,592 | 607,209 | 1,006,969 | [NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH:26]3[CH2:29][CH2:28][CH2:27]3)[C:10]3[C:15]([C:16]=2[C:17]#[N:18])=[CH:14][CH:13]=[C:12]([O:19][C:20]2[N:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[CH:11]=3)=[CH:4][C:3]=1[Cl:30].Cl[C:32]([O:34][CH:35]([CH3:37])[CH3:36])=[O:33]>C(Cl)Cl.N1C=CC=CC=1.C1(C)C=CC=CC=1.Cl>[CH:35]([O:34][C:32](=[O:33])[NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH:26]3[CH2:29][CH2:28][CH2:27]3)[C:10]3[C:15]([C:16]=2[C:17]#[N:18])=[CH:14][CH:13]=[C:12]([O:19][C:20]2[N:21]=[CH:22][CH:23]=[CH:24][N:25]=2)[CH:11]=3)=[CH:4][C:3]=1[Cl:30])([CH3:37])[CH3:36] | null | US07781478B2_3780 | 2,010 | Cc1ccccc1.Cl.ClCCl.Cl[C:5]([O:4][CH:2]([CH3:1])[CH3:3])=[O:6].[NH2:7][c:8]1[cH:9][cH:10][c:11](-[c:12]2[c:13]([C:14]#[N:15])[c:16]3[cH:17][cH:18][c:19]([O:20][c:21]4[n:22][cH:23][cH:24][cH:25][n:26]4)[cH:27][c:28]3[n:29]2[CH:30]2[CH2:31][CH2:32][CH2:33]2)[cH:34][c:35]1[Cl:36].c1ccncc1>>[CH3:1][CH:2]([CH3:3])[O:4][C:5](=[O:6])[NH:7][c:8]1[cH:9][cH:10][c:11](-[c:12]2[c:13]([C:14]#[N:15])[c:16]3[cH:17][cH:18][c:19]([O:20][c:21]4[n:22][cH:23][cH:24][cH:25][n:26]4)[cH:27][c:28]3[n:29]2[CH:30]2[CH2:31][CH2:32][CH2:33]2)[cH:34][c:35]1[Cl:36] | 0.756806 | CC(C)OC(=O)Cl.Cc1ccccc1.Cl.ClCCl.N#Cc1c(-c2ccc(N)c(Cl)c2)n(C2CCC2)c2cc(Oc3ncccn3)ccc12.c1ccncc1>>CC(C)OC(=O)Nc1ccc(-c2c(C#N)c3ccc(Oc4ncccn4)cc3n2C2CCC2)cc1Cl | CC(C)OC(=O)Cl.Cc1ccccc1.Cl.ClCCl.N#Cc1c(-c2ccc(N)c(Cl)c2)n(C2CCC2)c2cc(Oc3ncccn3)ccc12.c1ccncc1>>CC(C)OC(=O)Nc1ccc(-c2c(C#N)c3ccc(Oc4ncccn4)cc3n2C2CCC2)cc1Cl | US07781478B2_3780grants | 640fcf4ef4a061291e4868d36f60a03bbf37f13bc2e91e67b640c419 | Cc1ccccc1.Cl.ClCCl.Cl[C:5]([O:4][CH:2]([CH3:1])[CH3:3])=[O:6].[NH2:7][c:8]1[cH:9][cH:10][c:11](-[c:12]2[c:13]([C:14]#[N:15])[c:16]3[cH:17][cH:18][c:19]([O:20][c:21]4[n:22][cH:23][cH:24][cH:25][n:26]4)[cH:27][c:28]3[n:29]2[CH:30]2[CH2:31][CH2:32][CH2:33]2)[cH:34][c:35]1[Cl:36].c1ccncc1 | [CH3:1][CH:2]([CH3:3])[O:4][C:5](=[O:6])[NH:7][c:8]1[cH:9][cH:10][c:11](-[c:12]2[c:13]([C:14]#[N:15])[c:16]3[cH:17][cH:18][c:19]([O:20][c:21]4[n:22][cH:23][cH:24][cH:25][n:26]4)[cH:27][c:28]3[n:29]2[CH:30]2[CH2:31][CH2:32][CH2:33]2)[cH:34][c:35]1[Cl:36] | ([#8:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5])>>(Cl-[C;H0;D3;+0:1](-[#8:2])=[O;D1;H0:3]).([NH2;D1;+0:4]-[c:5]) | e639aa1de09b5a6fe2985a0569a19edb84e942b2ee65974484d93573 | 1 | 1 | Cc1ccccc1.Cl.ClCCl.c1ccncc1 | 102 |
248,742 | 825,852 | 1,368,854 | [CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([NH2:16])=[N:13][C:12]=1[CH2:17][N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:24](Cl)(=[O:33])[CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(N(CC)CC)C>O1CCCC1.CN(C)C1C=CN=CC=1>[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([NH:16][C:24](=[O:33])[CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[N:13][C:12]=1[CH2:17][N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1 | null | US08541457B2_0712 | 2,013 | C1CCOC1.CCN(CC)CC.CN(C)c1ccncc1.Cl[C:2](=[O:1])[CH2:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1.[NH2:11][c:12]1[n:13][c:14]([CH2:15][N:16]2[CH2:17][CH2:18][O:19][CH2:20][CH2:21]2)[c:22]([C:23](=[O:24])[NH:25][CH2:26][c:27]2[cH:28][cH:29][cH:30][cH:31][cH:32]2)[s:33]1>>[O:1]=[C:2]([CH2:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[NH:11][c:12]1[n:13][c:14]([CH2:15][N:16]2[CH2:17][CH2:18][O:19][CH2:20][CH2:21]2)[c:22]([C:23](=[O:24])[NH:25][CH2:26][c:27]2[cH:28][cH:29][cH:30][cH:31][cH:32]2)[s:33]1 | 0.814752 | C1CCOC1.CCN(CC)CC.CN(C)c1ccncc1.Nc1nc(CN2CCOCC2)c(C(=O)NCc2ccccc2)s1.O=C(Cl)CCc1ccccc1>>O=C(CCc1ccccc1)Nc1nc(CN2CCOCC2)c(C(=O)NCc2ccccc2)s1 | C1CCOC1.CCN(CC)CC.CN(C)c1ccncc1.Nc1nc(CN2CCOCC2)c(C(=O)NCc2ccccc2)s1.O=C(Cl)CCc1ccccc1>>O=C(CCc1ccccc1)Nc1nc(CN2CCOCC2)c(C(=O)NCc2ccccc2)s1 | US08541457B2_0712grants | 8e051d5ca70c227c130579e67ee5a5413cafec4465e27d66f414e775 | C1CCOC1.CCN(CC)CC.CN(C)c1ccncc1.Cl[C:2](=[O:1])[CH2:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1.[NH2:11][c:12]1[n:13][c:14]([CH2:15][N:16]2[CH2:17][CH2:18][O:19][CH2:20][CH2:21]2)[c:22]([C:23](=[O:24])[NH:25][CH2:26][c:27]2[cH:28][cH:29][cH:30][cH:31][cH:32]2)[s:33]1 | [O:1]=[C:2]([CH2:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[NH:11][c:12]1[n:13][c:14]([CH2:15][N:16]2[CH2:17][CH2:18][O:19][CH2:20][CH2:21]2)[c:22]([C:23](=[O:24])[NH:25][CH2:26][c:27]2[cH:28][cH:29][cH:30][cH:31][cH:32]2)[s:33]1 | ([#16;a:4]:[c:5](:[#7;a:6])-[NH;D2;+0:7]-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3])>>(Cl-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([#16;a:4]:[c:5](:[#7;a:6])-[NH2;D1;+0:7]) | fb0e611d9aa0d97d0fa7ba32c78621db605b5592c522863c5957a0dd | 1 | 1 | C1CCOC1.CCN(CC)CC.CN(C)c1ccncc1 | 553 |
314,677 | 1,023,239 | 1,731,592 | Cl[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[CH3:14][NH2:15].Cl>O>[CH3:14][NH:15][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12] | null | US09273030B2_0229 | 2,016 | Cl.Cl[c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[OH:9])[cH:10][c:11]1[N+:12](=[O:13])[O-:14].O.[CH3:1][NH2:2]>>[CH3:1][NH:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[OH:9])[cH:10][c:11]1[N+:12](=[O:13])[O-:14] | 0.962803 | CN.Cl.O.O=C(O)c1ccc(Cl)c([N+](=O)[O-])c1>>CNc1ccc(C(=O)O)cc1[N+](=O)[O-] | CN.Cl.O.O=C(O)c1ccc(Cl)c([N+](=O)[O-])c1>>CNc1ccc(C(=O)O)cc1[N+](=O)[O-] | US09273030B2_0229grants | 946ebebfc32cb9c74faa7e826cb9b0fb82f5e61b568dd71beead976e | Cl.Cl[c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[OH:9])[cH:10][c:11]1[N+:12](=[O:13])[O-:14].O.[CH3:1][NH2:2] | [CH3:1][NH:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[OH:9])[cH:10][c:11]1[N+:12](=[O:13])[O-:14] | ([C;D1;H3:4]-[NH;D2;+0:5]-[c;H0;D3;+0:1](:[c:2]):[c:3])>>(Cl-[c;H0;D3;+0:1](:[c:2]):[c:3]).([C;D1;H3:4]-[NH2;D1;+0:5]) | d123565ed644ccc6f54e36123787f5906b57fd501e36d0d80af555c4 | 1 | 1 | Cl.O | 304 |
123,622 | 456,137 | 772,993 | [OH:1][C:2]1[C:3]([C:8]([O:10][CH3:11])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl>CC(C)=O.O>[CH2:18]([O:1][C:2]1[C:3]([C:8]([O:10][CH3:11])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1 | |f:1.2.3| | US07183278B1_0262 | 2,007 | Br[CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1.CC(C)=O.Cl.O.O=C([O-])[O-].[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][cH:7][cH:8][cH:9][c:10]1[OH:11].[K+].[K+]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][cH:7][cH:8][cH:9][c:10]1[O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | 0.954443 | BrCc1ccccc1.CC(C)=O.COC(=O)c1ncccc1O.Cl.O.O=C([O-])[O-]~[K+]~[K+]>>COC(=O)c1ncccc1OCc1ccccc1 | BrCc1ccccc1.CC(C)=O.COC(=O)c1ncccc1O.Cl.O.O=C([O-])[O-].[K+].[K+]>>COC(=O)c1ncccc1OCc1ccccc1 | US07183278B1_0262grants | 0a30e1ca2e10e52850f4552035033c20c66f966dd356b5535b578a04 | Br[CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1.CC(C)=O.Cl.O.O=C([O-])[O-].[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][cH:7][cH:8][cH:9][c:10]1[OH:11].[K+].[K+] | [CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][cH:7][cH:8][cH:9][c:10]1[O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | ([#7;a:3]:[c:4]:[c:5]-[O;H0;D2;+0:6]-[CH2;D2;+0:1]-[c:2])>>(Br-[CH2;D2;+0:1]-[c:2]).([#7;a:3]:[c:4]:[c:5]-[OH;D1;+0:6]) | 06e557c95c6218f60f489a91667cd0e33186c90d7412366ea77aef20 | 1 | 1 | CC(C)=O.Cl.O.O=C([O-])[O-].[K+].[K+] | 623 |
339,517 | 289,220 | null | Br[C:2]1[S:3][C:4]([Br:7])=[CH:5][N:6]=1.[CH3:8][N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1>CN(C1C=CN=CC=1)C.C(O)CCC>[Br:7][C:4]1[S:3][C:2]([N:12]2[CH2:13][CH2:14][N:9]([CH3:8])[CH2:10][CH2:11]2)=[N:6][CH:5]=1 | null | US20050222410A1_0283 | 2,005 | Br[c:6]1[n:7][cH:8][c:9]([Br:10])[s:11]1.CCCCO.CN(C)c1ccncc1.[CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH2:12][CH2:13]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[n:7][cH:8][c:9]([Br:10])[s:11]2)[CH2:12][CH2:13]1 | 0.78651 | Brc1cnc(Br)s1.CCCCO.CN(C)c1ccncc1.CN1CCNCC1>>CN1CCN(c2ncc(Br)s2)CC1 | Brc1cnc(Br)s1.CCCCO.CN(C)c1ccncc1.CN1CCNCC1>>CN1CCN(c2ncc(Br)s2)CC1 | US20050222410A1_0283apps | 273f947bd83743840fd59cf8e92721419130430b6f5bc978d18f6983 | Br[c:6]1[n:7][cH:8][c:9]([Br:10])[s:11]1.CCCCO.CN(C)c1ccncc1.[CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH2:12][CH2:13]1 | [CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[n:7][cH:8][c:9]([Br:10])[s:11]2)[CH2:12][CH2:13]1 | ([#16;a:2]:[c;H0;D3;+0:1](:[#7;a:3])-[N;H0;D3;+0:5](-[C:4])-[C:6])>>(Br-[c;H0;D3;+0:1](:[#16;a:2]):[#7;a:3]).([C:4]-[NH;D2;+0:5]-[C:6]) | 53c334f21890a3a530f4d5497f5df8245897b0e169dadf5160559f17 | 1 | 1 | CCCCO.CN(C)c1ccncc1 | 657 |
360,268 | 624,776 | null | Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([NH:10][C@H:11]2[CH2:15][CH2:14][O:13][CH2:12]2)[CH:3]=1.[CH3:16][C:17]1[C:25]2[C:24](=[O:26])[CH2:23][C:22]([CH3:28])([CH3:27])[CH2:21][C:20]=2[NH:19][CH:18]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1>[O:13]1[CH2:14][CH2:15][C@H:11]([NH:10][C:4]2[CH:3]=[C:2]([N:19]3[C:20]4[CH2:21][C:22]([CH3:27])([CH3:28])[CH2:23][C:24](=[O:26])[C:25]=4[C:17]([CH3:16])=[CH:18]3)[CH:9]=[CH:8][C:5]=2[C:6]#[N:7])[CH2:12]1 | |f:2.3.4| | US20080269193A1_0699 | 2,008 | Br[c:5]1[cH:6][cH:7][c:8]([C:9]#[N:10])[c:11]([NH:12][C@H:13]2[CH2:14][CH2:15][O:16][CH2:17]2)[cH:18]1.C1COCCO1.O=C([O-])[O-].[CH3:1][c:2]1[cH:3][nH:4][c:19]2[c:20]1[C:21](=[O:22])[CH2:23][C:24]([CH3:25])([CH3:26])[CH2:27]2.[K+].[K+]>>[CH3:1][c:2]1[cH:3][n:4](-[c:5]2[cH:6][cH:7][c:8]([C:9]#[N:10])[c:11]([NH:12][C@H:13]3[CH2:14][CH2:15][O:16][CH2:17]3)[cH:18]2)[c:19]2[c:20]1[C:21](=[O:22])[CH2:23][C:24]([CH3:25])([CH3:26])[CH2:27]2 | 0.696771 | C1COCCO1.Cc1c[nH]c2c1C(=O)CC(C)(C)C2.N#Cc1ccc(Br)cc1N[C@H]1CCOC1.O=C([O-])[O-]~[K+]~[K+]>>Cc1cn(-c2ccc(C#N)c(N[C@H]3CCOC3)c2)c2c1C(=O)CC(C)(C)C2 | C1COCCO1.Cc1c[nH]c2c1C(=O)CC(C)(C)C2.N#Cc1ccc(Br)cc1N[C@H]1CCOC1.O=C([O-])[O-].[K+].[K+]>>Cc1cn(-c2ccc(C#N)c(N[C@H]3CCOC3)c2)c2c1C(=O)CC(C)(C)C2 | US20080269193A1_0699apps | b1ba581a14c1fc7e2f4c2efc9b7d467bc3c8763f8f6684eedbb3c0a9 | Br[c:5]1[cH:6][cH:7][c:8]([C:9]#[N:10])[c:11]([NH:12][C@H:13]2[CH2:14][CH2:15][O:16][CH2:17]2)[cH:18]1.C1COCCO1.O=C([O-])[O-].[CH3:1][c:2]1[cH:3][nH:4][c:19]2[c:20]1[C:21](=[O:22])[CH2:23][C:24]([CH3:25])([CH3:26])[CH2:27]2.[K+].[K+] | [CH3:1][c:2]1[cH:3][n:4](-[c:5]2[cH:6][cH:7][c:8]([C:9]#[N:10])[c:11]([NH:12][C@H:13]3[CH2:14][CH2:15][O:16][CH2:17]3)[cH:18]2)[c:19]2[c:20]1[C:21](=[O:22])[CH2:23][C:24]([CH3:25])([CH3:26])[CH2:27]2 | ([c:2]:[c;H0;D3;+0:1](:[c:3])-[n;H0;D3;+0:5](:[c:4]):[c:6])>>(Br-[c;H0;D3;+0:1](:[c:2]):[c:3]).([c:4]:[nH;D2;+0:5]:[c:6]) | 3fe034cccad6980ec2d3a1de437611ce8e22696c412d2117aaa7c4a7 | 1 | 1 | C1COCCO1.O=C([O-])[O-].[K+].[K+] | 349 |
366,666 | 704,633 | null | [Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:14]C)=[C:6]([CH2:8][C:9]([N:11]([CH3:13])[CH3:12])=[O:10])[CH:7]=1.B(Br)(Br)Br.C(OCC)C>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:14])=[C:6]([CH2:8][C:9]([N:11]([CH3:13])[CH3:12])=[O:10])[CH:7]=1 | null | US20090130090A1_0423 | 2,009 | BrB(Br)Br.CCOCC.C[O:14][c:13]1[c:7]([CH2:6][C:4]([N:2]([CH3:1])[CH3:3])=[O:5])[cH:8][c:9]([Cl:10])[cH:11][cH:12]1.ClCCl>>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[CH2:6][c:7]1[cH:8][c:9]([Cl:10])[cH:11][cH:12][c:13]1[OH:14] | 0.528281 | BrB(Br)Br.CCOCC.COc1ccc(Cl)cc1CC(=O)N(C)C.ClCCl>>CN(C)C(=O)Cc1cc(Cl)ccc1O | BrB(Br)Br.CCOCC.COc1ccc(Cl)cc1CC(=O)N(C)C.ClCCl>>CN(C)C(=O)Cc1cc(Cl)ccc1O | US20090130090A1_0423apps | 9560e81b738ae13040a746677147c958a02aea39badacefb45871821 | BrB(Br)Br.CCOCC.C[O:14][c:13]1[c:7]([CH2:6][C:4]([N:2]([CH3:1])[CH3:3])=[O:5])[cH:8][c:9]([Cl:10])[cH:11][cH:12]1.ClCCl | [CH3:1][N:2]([CH3:3])[C:4](=[O:5])[CH2:6][c:7]1[cH:8][c:9]([Cl:10])[cH:11][cH:12][c:13]1[OH:14] | ([OH;D1;+0:1]-[c:2])>>(C-[O;H0;D2;+0:1]-[c:2]) | f50e6edd43215fd09e75ad8277fe209f633bdb24972a58fad4063f8f | 1 | 1 | BrB(Br)Br.CCOCC.ClCCl | 48 |
62,912 | 264,902 | 448,243 | C[O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:14][CH:13]=2)[CH:5]=1.[OH-].[Na+]>O.C(O)C>[C:15]1([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:16]=[CH:17][C:12]([O:11][CH2:10][C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[C:3]([OH:24])=[O:2])=[CH:13][CH:14]=1 | |f:1.2| | US05958957_ | 1,999 | CCO.C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][cH:7][c:8]([CH2:9][O:10][c:11]2[cH:12][cH:13][c:14](-[c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[cH:21][cH:22]2)[cH:23]1.O.[Na+].[OH-]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([CH2:9][O:10][c:11]2[cH:12][cH:13][c:14](-[c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[cH:21][cH:22]2)[cH:23]1 | 0.854071 | CCO.COC(=O)c1cccc(COc2ccc(-c3ccccc3)cc2)c1.O.[Na+]~[OH-]>>O=C(O)c1cccc(COc2ccc(-c3ccccc3)cc2)c1 | CCO.COC(=O)c1cccc(COc2ccc(-c3ccccc3)cc2)c1.O.[Na+].[OH-]>>O=C(O)c1cccc(COc2ccc(-c3ccccc3)cc2)c1 | US05958957_grants | 7170889dbd4fdfaff04d5fa528e9b5a8bf54ccb5a44428e0eb9d95d3 | CCO.C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][cH:7][c:8]([CH2:9][O:10][c:11]2[cH:12][cH:13][c:14](-[c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[cH:21][cH:22]2)[cH:23]1.O.[Na+].[OH-] | [O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([CH2:9][O:10][c:11]2[cH:12][cH:13][c:14](-[c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[cH:21][cH:22]2)[cH:23]1 | ([O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4]1:[c:5]:[c:6]:[c:7]:[c:8]:[c:9]:1)>>(C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[c:5]:[c:6]:[c:7]:[c:8]:[c:9]:1) | 48f3c58ed4b2eb976195200c79ebaafb36d7eb1c6248c7c6424a4457 | 1 | 1 | CCO.O.[Na+].[OH-] | 247 |
141,273 | 509,668 | 854,953 | [NH2:1][C:2]1[C:7]([C:8]([C:10]2[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[C:12]([F:18])[C:11]=2[F:19])=[O:9])=[CH:6][CH:5]=[C:4](Cl)[N:3]=1.[NH2:21][CH:22]1[CH2:27][CH2:26][N:25]([C:28](=[O:30])[CH3:29])[CH2:24][CH2:23]1>>[NH2:1][C:2]1[N:3]=[C:4]([NH:21][CH:22]2[CH2:27][CH2:26][N:25]([C:28](=[O:30])[CH3:29])[CH2:24][CH2:23]2)[CH:5]=[CH:6][C:7]=1[C:8](=[O:9])[C:10]1[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[C:12]([F:18])[C:11]=1[F:19] | null | US07423051B2_0368 | 2,008 | Cl[c:16]1[cH:15][cH:14][c:13]([C:11]([c:10]2[c:3]([O:2][CH3:1])[cH:4][cH:5][c:6]([F:7])[c:8]2[F:9])=[O:12])[c:28]([NH2:29])[n:27]1.[NH2:17][CH:18]1[CH2:19][CH2:20][N:21]([C:22]([CH3:23])=[O:24])[CH2:25][CH2:26]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([F:7])[c:8]([F:9])[c:10]1[C:11](=[O:12])[c:13]1[cH:14][cH:15][c:16]([NH:17][CH:18]2[CH2:19][CH2:20][N:21]([C:22]([CH3:23])=[O:24])[CH2:25][CH2:26]2)[n:27][c:28]1[NH2:29] | 0.969178 | CC(=O)N1CCC(N)CC1.COc1ccc(F)c(F)c1C(=O)c1ccc(Cl)nc1N>>COc1ccc(F)c(F)c1C(=O)c1ccc(NC2CCN(C(C)=O)CC2)nc1N | CC(=O)N1CCC(N)CC1.COc1ccc(F)c(F)c1C(=O)c1ccc(Cl)nc1N>>COc1ccc(F)c(F)c1C(=O)c1ccc(NC2CCN(C(C)=O)CC2)nc1N | US07423051B2_0368grants | 390dedab3e4a41222c23b1788fd1cd4e7ff593135340a09acb3df5e8 | Cl[c:16]1[cH:15][cH:14][c:13]([C:11]([c:10]2[c:3]([O:2][CH3:1])[cH:4][cH:5][c:6]([F:7])[c:8]2[F:9])=[O:12])[c:28]([NH2:29])[n:27]1.[NH2:17][CH:18]1[CH2:19][CH2:20][N:21]([C:22]([CH3:23])=[O:24])[CH2:25][CH2:26]1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([F:7])[c:8]([F:9])[c:10]1[C:11](=[O:12])[c:13]1[cH:14][cH:15][c:16]([NH:17][CH:18]2[CH2:19][CH2:20][N:21]([C:22]([CH3:23])=[O:24])[CH2:25][CH2:26]2)[n:27][c:28]1[NH2:29] | ([#7;a:2]:[c;H0;D3;+0:1](:[c:3])-[NH;D2;+0:5]-[C:4])>>(Cl-[c;H0;D3;+0:1](:[#7;a:2]):[c:3]).([C:4]-[NH2;D1;+0:5]) | b7dcca1715ae4f4860ce60c58aa7a841fe17b3f404fb48a132c70869 | 1 | 1 | null | 70 |
405,953 | 1,536,349 | null | [CH3:1][N:2]([CH3:14])[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][CH:6]=1>CO.[Pd]>[CH3:14][N:2]([CH3:1])[CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([NH2:11])=[CH:9][CH:10]=1 | null | US20140163026A1_0833 | 2,014 | CO.O=[N+:10]([O-])[c:9]1[cH:8][cH:7][c:6]([CH2:5][CH2:4][N:2]([CH3:1])[CH3:3])[cH:12][cH:11]1.[Pd]>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][c:6]1[cH:7][cH:8][c:9]([NH2:10])[cH:11][cH:12]1 | 0.905958 | CN(C)CCc1ccc([N+](=O)[O-])cc1.CO.[Pd]>>CN(C)CCc1ccc(N)cc1 | CN(C)CCc1ccc([N+](=O)[O-])cc1.CO.[Pd]>>CN(C)CCc1ccc(N)cc1 | US20140163026A1_0833apps | 9bd69d1fa84be4098f9b5e631c45995a29cb38d0eb9dcd9b2855d8ec | CO.O=[N+:10]([O-])[c:9]1[cH:8][cH:7][c:6]([CH2:5][CH2:4][N:2]([CH3:1])[CH3:3])[cH:12][cH:11]1.[Pd] | [CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][c:6]1[cH:7][cH:8][c:9]([NH2:10])[cH:11][cH:12]1 | ([NH2;D1;+0:1]-[c:2])>>(O=[N+;H0;D3:1](-[O-])-[c:2]) | f0a489cd79c24ed642d5256650cdb0f98e5344b2c074824b17336ecc | 1 | 1 | CO.[Pd] | 1 |
280,879 | 919,952 | 1,539,322 | [Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[N:6][CH:7]=1.Cl.[CH2:10]1[C:13]2([CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH2:12][CH:11]1[OH:19].C(N(CC)C(C)C)(C)C.CN(C=O)C>C(#N)C.C(OCC)(=O)C.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:16]2[CH2:17][CH2:18][C:13]3([CH2:10][CH:11]([OH:19])[CH2:12]3)[CH2:14][CH2:15]2)=[N:6][CH:7]=1 | |f:1.2| | US08889702B2_0268 | 2,014 | CC#N.CCN(C(C)C)C(C)C.CCOC(C)=O.CN(C)C=O.Cl.F[c:8]1[cH:9][cH:10][c:11]([Br:12])[cH:13][n:14]1.O.[OH:1][CH:2]1[CH2:3][C:4]2([CH2:5][CH2:6][NH:7][CH2:15][CH2:16]2)[CH2:17]1>>[OH:1][CH:2]1[CH2:3][C:4]2([CH2:5][CH2:6][N:7]([c:8]3[cH:9][cH:10][c:11]([Br:12])[cH:13][n:14]3)[CH2:15][CH2:16]2)[CH2:17]1 | 0.937731 | CC#N.CCN(C(C)C)C(C)C.CCOC(C)=O.CN(C)C=O.Cl~OC1CC2(CCNCC2)C1.Fc1ccc(Br)cn1.O>>OC1CC2(CCN(c3ccc(Br)cn3)CC2)C1 | CC#N.CCN(C(C)C)C(C)C.CCOC(C)=O.CN(C)C=O.Cl.Fc1ccc(Br)cn1.O.OC1CC2(CCNCC2)C1>>OC1CC2(CCN(c3ccc(Br)cn3)CC2)C1 | US08889702B2_0268grants | e119733e84b4fc794c8506a88feaecfe7380f11ab102fb2e794e08d2 | CC#N.CCN(C(C)C)C(C)C.CCOC(C)=O.CN(C)C=O.Cl.F[c:8]1[cH:9][cH:10][c:11]([Br:12])[cH:13][n:14]1.O.[OH:1][CH:2]1[CH2:3][C:4]2([CH2:5][CH2:6][NH:7][CH2:15][CH2:16]2)[CH2:17]1 | [OH:1][CH:2]1[CH2:3][C:4]2([CH2:5][CH2:6][N:7]([c:8]3[cH:9][cH:10][c:11]([Br:12])[cH:13][n:14]3)[CH2:15][CH2:16]2)[CH2:17]1 | ([#7;a:2]:[c;H0;D3;+0:1](:[c:3])-[N;H0;D3;+0:5](-[C:4])-[C:6])>>(F-[c;H0;D3;+0:1](:[#7;a:2]):[c:3]).([C:4]-[NH;D2;+0:5]-[C:6]) | 75f5c3b5931acefdaede4105af581f1b0cf902ee909a493ac1252c46 | 1 | 1 | CC#N.CCN(C(C)C)C(C)C.CCOC(C)=O.CN(C)C=O.Cl.O | 756 |
189,392 | 652,698 | 1,078,420 | [Br:1][C:2]1[CH:3]=[N:4][C:5]2[N:6]([N:8]=[C:9]([C:11]([OH:13])=O)[CH:10]=2)[CH:7]=1.[CH2:14]([CH:16]1[C:21]2[CH:22]=[CH:23][S:24][C:20]=2[CH2:19][CH2:18][NH:17]1)[CH3:15]>>[Br:1][C:2]1[CH:3]=[N:4][C:5]2[N:6]([N:8]=[C:9]([C:11]([N:17]3[CH2:18][CH2:19][C:20]4[S:24][CH:23]=[CH:22][C:21]=4[CH:16]3[CH2:14][CH3:15])=[O:13])[CH:10]=2)[CH:7]=1 | null | US07947689B2_0591 | 2,011 | O[C:12](=[O:13])[c:14]1[cH:15][c:16]2[n:17][cH:18][c:19]([Br:20])[cH:21][n:22]2[n:23]1.[CH3:1][CH2:2][CH:3]1[c:4]2[cH:5][cH:6][s:7][c:8]2[CH2:9][CH2:10][NH:11]1>>[CH3:1][CH2:2][CH:3]1[c:4]2[cH:5][cH:6][s:7][c:8]2[CH2:9][CH2:10][N:11]1[C:12](=[O:13])[c:14]1[cH:15][c:16]2[n:17][cH:18][c:19]([Br:20])[cH:21][n:22]2[n:23]1 | 0.883639 | CCC1NCCc2sccc21.O=C(O)c1cc2ncc(Br)cn2n1>>CCC1c2ccsc2CCN1C(=O)c1cc2ncc(Br)cn2n1 | CCC1NCCc2sccc21.O=C(O)c1cc2ncc(Br)cn2n1>>CCC1c2ccsc2CCN1C(=O)c1cc2ncc(Br)cn2n1 | US07947689B2_0591grants | 9a57f8e9d7c1cca30c0af84ab90a1f866516f52e58e9ea05a04b263a | O[C:12](=[O:13])[c:14]1[cH:15][c:16]2[n:17][cH:18][c:19]([Br:20])[cH:21][n:22]2[n:23]1.[CH3:1][CH2:2][CH:3]1[c:4]2[cH:5][cH:6][s:7][c:8]2[CH2:9][CH2:10][NH:11]1 | [CH3:1][CH2:2][CH:3]1[c:4]2[cH:5][cH:6][s:7][c:8]2[CH2:9][CH2:10][N:11]1[C:12](=[O:13])[c:14]1[cH:15][c:16]2[n:17][cH:18][c:19]([Br:20])[cH:21][n:22]2[n:23]1 | ([#7;a:5]:[#7;a:4]:[c:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:7](-[C:6])-[C:8])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]:[#7;a:4]:[#7;a:5]).([C:6]-[NH;D2;+0:7]-[C:8]) | 3b2f6aec0a5b15474e8d3e5e54c77d4c7a6db409c225cfbbb1c66d17 | 1 | 1 | null | 663 |
275,929 | 905,036 | 1,509,761 | [CH2:1]([N:8]1[CH2:13][C:12]([CH3:15])([CH3:14])[O:11][C:10]2([CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[F:27][C:28]([F:39])([F:38])[C:29](O[C:29](=[O:30])[C:28]([F:39])([F:38])[F:27])=[O:30]>C(Cl)Cl>[CH2:1]([N:8]1[CH2:13][C:12]([CH3:15])([CH3:14])[O:11][C:10]2([CH2:20][CH2:19][N:18]([C:29](=[O:30])[C:28]([F:39])([F:38])[F:27])[CH2:17][CH2:16]2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1 | null | US08828996B2_0295 | 2,014 | ClCCl.O=C(O[C:18](=[O:19])[C:20]([F:21])([F:22])[F:23])C(F)(F)F.[CH3:1][C:2]1([CH3:3])[CH2:4][N:5]([CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[CH2:13][C:14]2([CH2:15][CH2:16][NH:17][CH2:24][CH2:25]2)[O:26]1.c1ccncc1>>[CH3:1][C:2]1([CH3:3])[CH2:4][N:5]([CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[CH2:13][C:14]2([CH2:15][CH2:16][N:17]([C:18](=[O:19])[C:20]([F:21])([F:22])[F:23])[CH2:24][CH2:25]2)[O:26]1 | 0.173406 | CC1(C)CN(Cc2ccccc2)CC2(CCNCC2)O1.ClCCl.O=C(OC(=O)C(F)(F)F)C(F)(F)F.c1ccncc1>>CC1(C)CN(Cc2ccccc2)CC2(CCN(C(=O)C(F)(F)F)CC2)O1 | CC1(C)CN(Cc2ccccc2)CC2(CCNCC2)O1.ClCCl.O=C(OC(=O)C(F)(F)F)C(F)(F)F.c1ccncc1>>CC1(C)CN(Cc2ccccc2)CC2(CCN(C(=O)C(F)(F)F)CC2)O1 | US08828996B2_0295grants | f9e11998cb655474756ae1e4e5bfdad8e9baaf81f3d670ec7242df4f | ClCCl.O=C(O[C:18](=[O:19])[C:20]([F:21])([F:22])[F:23])C(F)(F)F.[CH3:1][C:2]1([CH3:3])[CH2:4][N:5]([CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[CH2:13][C:14]2([CH2:15][CH2:16][NH:17][CH2:24][CH2:25]2)[O:26]1.c1ccncc1 | [CH3:1][C:2]1([CH3:3])[CH2:4][N:5]([CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[CH2:13][C:14]2([CH2:15][CH2:16][N:17]([C:18](=[O:19])[C:20]([F:21])([F:22])[F:23])[CH2:24][CH2:25]2)[O:26]1 | ([C:7]-[N;H0;D3;+0:8](-[C:9])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[F;D1;H0:4])(-[F;D1;H0:5])-[F;D1;H0:6])>>(F-C(-F)(-F)-C(=O)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[F;D1;H0:4])(-[F;D1;H0:5])-[F;D1;H0:6]).([C:7]-[NH;D2;+0:8]-[C:9]) | 97c28e938bcf0cb31d82f4bdedc18f10d3e6d8f38e30aa8639311706 | 1 | 1 | ClCCl.c1ccncc1 | 397 |
368,359 | 737,773 | null | C([O:8][C:9]1[C:10]([Cl:35])=[CH:11][C:12]([Cl:34])=[C:13]([C:15]2[N:23]=[C:22]([Cl:24])[N:21]=[C:20]3[C:16]=2[N:17]=[CH:18][N:19]3[CH2:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)[CH:14]=1)C1C=CC=CC=1.B(Cl)(Cl)Cl>ClCCl>[Cl:35][C:10]1[CH:11]=[C:12]([Cl:34])[C:13]([C:15]2[N:23]=[C:22]([Cl:24])[N:21]=[C:20]3[C:16]=2[N:17]=[CH:18][N:19]3[CH2:25][C:26]2[CH:27]=[CH:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=2)=[CH:14][C:9]=1[OH:8] | null | US20090181989A1_0297 | 2,009 | ClB(Cl)Cl.ClCCl.c1ccc(C[O:16][c:15]2[cH:14][c:13](-[c:12]3[c:11]4[n:10][cH:9][n:8]([CH2:7][c:6]5[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:28][cH:27]5)[c:26]4[n:25][c:23]([Cl:24])[n:22]3)[c:20]([Cl:21])[cH:19][c:17]2[Cl:18])cc1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][n:8]2[cH:9][n:10][c:11]3[c:12](-[c:13]4[cH:14][c:15]([OH:16])[c:17]([Cl:18])[cH:19][c:20]4[Cl:21])[n:22][c:23]([Cl:24])[n:25][c:26]23)[cH:27][cH:28]1 | 0.956865 | COc1ccc(Cn2cnc3c(-c4cc(OCc5ccccc5)c(Cl)cc4Cl)nc(Cl)nc32)cc1.ClB(Cl)Cl.ClCCl>>COc1ccc(Cn2cnc3c(-c4cc(O)c(Cl)cc4Cl)nc(Cl)nc32)cc1 | COc1ccc(Cn2cnc3c(-c4cc(OCc5ccccc5)c(Cl)cc4Cl)nc(Cl)nc32)cc1.ClB(Cl)Cl.ClCCl>>COc1ccc(Cn2cnc3c(-c4cc(O)c(Cl)cc4Cl)nc(Cl)nc32)cc1 | US20090181989A1_0297apps | 9594a6f4b78ca8a137140dec52be61449f2f05b9f2b6972e3afdd352 | ClB(Cl)Cl.ClCCl.c1ccc(C[O:16][c:15]2[cH:14][c:13](-[c:12]3[c:11]4[n:10][cH:9][n:8]([CH2:7][c:6]5[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:28][cH:27]5)[c:26]4[n:25][c:23]([Cl:24])[n:22]3)[c:20]([Cl:21])[cH:19][c:17]2[Cl:18])cc1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][n:8]2[cH:9][n:10][c:11]3[c:12](-[c:13]4[cH:14][c:15]([OH:16])[c:17]([Cl:18])[cH:19][c:20]4[Cl:21])[n:22][c:23]([Cl:24])[n:25][c:26]23)[cH:27][cH:28]1 | ([OH;D1;+0:2]-[c:1])>>([c:1]-[O;H0;D2;+0:2]-C-c1:c:c:c:c:c:1) | 5aae93a61569145ed18632d801932cdc99b7a496825e1c5156904263 | 1 | 1 | ClB(Cl)Cl.ClCCl | 23 |
360,775 | 629,747 | null | [C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:27][C:26]2[CH:28]=[C:22]([CH:23]=[CH:24][C:25]=2[OH:29])[C:21]2=[CH:30][C:17](=[CH:18][CH:19]=[CH:20]2)[CH2:16][C@@H:15]([C:31](O)=[O:32])[NH:14][C:13](=[O:34])[C@H:12]([CH2:35][CH2:36][CH2:37][NH:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[NH:11][C:10]1=[O:46])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:47][C@H:48]([C:60]([NH:62][CH2:63][C@@H:64]([NH:76][C:77]([O:79][C:80]([CH3:83])([CH3:82])[CH3:81])=[O:78])[CH2:65][CH2:66][CH2:67][NH:68][C:69]([O:71][C:72]([CH3:75])([CH3:74])[CH3:73])=[O:70])=[O:61])[CH2:49][CH2:50][CH2:51][NH:52][C:53](=[O:59])[O:54][C:55]([CH3:58])([CH3:57])[CH3:56].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[C:80]([O:79][C:77]([NH:76][C@@H:64]([CH2:65][CH2:66][CH2:67][NH:68][C:69]([O:71][C:72]([CH3:73])([CH3:74])[CH3:75])=[O:70])[CH2:63][NH:62][C:60](=[O:61])[C@@H:48]([NH:47][C:31]([C@H:15]1[NH:14][C:13](=[O:34])[C@H:12]([CH2:35][CH2:36][CH2:37][NH:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[NH:11][C:10](=[O:46])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:27][C:26]2[CH:28]=[C:22]([CH:23]=[CH:24][C:25]=2[OH:29])[C:21]2=[CH:30][C:17](=[CH:18][CH:19]=[CH:20]2)[CH2:16]1)=[O:32])[CH2:49][CH2:50][CH2:51][NH:52][C:53](=[O:59])[O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:78])([CH3:83])([CH3:82])[CH3:81] | null | US20080275018A1_1092 | 2,008 | CN(C)C=O.ClCCCl.O[C:30](=[O:31])[C@@H:32]1[CH2:33][c:34]2[cH:35][cH:36][cH:37][c:38]([cH:39]2)-[c:40]2[cH:41][cH:42][c:43]([OH:44])[c:45]([cH:46]2)[CH2:47][C@H:48]([NH:49][C:50](=[O:51])[O:52][C:53]([CH3:54])([CH3:55])[CH3:56])[C:57](=[O:58])[NH:59][C@@H:60]([CH2:61][CH2:62][CH2:63][NH:64][C:65](=[O:66])[O:67][C:68]([CH3:69])([CH3:70])[CH3:71])[C:72](=[O:73])[NH:74]1.On1nnc2ccccc21.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH2:11][C@@H:12]([CH2:13][NH:14][C:15](=[O:16])[C@H:17]([CH2:18][CH2:19][CH2:20][NH:21][C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[NH2:29])[NH:75][C:76](=[O:77])[O:78][C:79]([CH3:80])([CH3:81])[CH3:82]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH2:11][C@@H:12]([CH2:13][NH:14][C:15](=[O:16])[C@H:17]([CH2:18][CH2:19][CH2:20][NH:21][C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[NH:29][C:30](=[O:31])[C@@H:32]1[CH2:33][c:34]2[cH:35][cH:36][cH:37][c:38]([cH:39]2)-[c:40]2[cH:41][cH:42][c:43]([OH:44])[c:45]([cH:46]2)[CH2:47][C@H:48]([NH:49][C:50](=[O:51])[O:52][C:53]([CH3:54])([CH3:55])[CH3:56])[C:57](=[O:58])[NH:59][C@@H:60]([CH2:61][CH2:62][CH2:63][NH:64][C:65](=[O:66])[O:67][C:68]([CH3:69])([CH3:70])[CH3:71])[C:72](=[O:73])[NH:74]1)[NH:75][C:76](=[O:77])[O:78][C:79]([CH3:80])([CH3:81])[CH3:82] | 0.016054 | CC(C)(C)OC(=O)NCCC[C@@H]1NC(=O)[C@@H](NC(=O)OC(C)(C)C)Cc2cc(ccc2O)-c2cccc(c2)C[C@@H](C(=O)O)NC1=O.CC(C)(C)OC(=O)NCCC[C@H](N)C(=O)NC[C@H](CCCNC(=O)OC(C)(C)C)NC(=O)OC(C)(C)C.CN(C)C=O.ClCCCl.On1nnc2ccccc21>>CC(C)(C)OC(=O)NCCC[C@H](NC(=O)[C@@H]1Cc2cccc(c2)-c2ccc(O)c(c2)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@@H](CCCNC(=O)OC(C)(C)C)C(=O)N1)C(=O)NC[C@H](CCCNC(=O)OC(C)(C)C)NC(=O)OC(C)(C)C | CC(C)(C)OC(=O)NCCC[C@@H]1NC(=O)[C@@H](NC(=O)OC(C)(C)C)Cc2cc(ccc2O)-c2cccc(c2)C[C@@H](C(=O)O)NC1=O.CC(C)(C)OC(=O)NCCC[C@H](N)C(=O)NC[C@H](CCCNC(=O)OC(C)(C)C)NC(=O)OC(C)(C)C.CN(C)C=O.ClCCCl.On1nnc2ccccc21>>CC(C)(C)OC(=O)NCCC[C@H](NC(=O)[C@@H]1Cc2cccc(c2)-c2ccc(O)c(c2)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@@H](CCCNC(=O)OC(C)(C)C)C(=O)N1)C(=O)NC[C@H](CCCNC(=O)OC(C)(C)C)NC(=O)OC(C)(C)C | US20080275018A1_1092apps | bdf60e6e4f538b8b10f9d6d7852080c56f9671df96c9f6f874c78d45 | CN(C)C=O.ClCCCl.O[C:30](=[O:31])[C@@H:32]1[CH2:33][c:34]2[cH:35][cH:36][cH:37][c:38]([cH:39]2)-[c:40]2[cH:41][cH:42][c:43]([OH:44])[c:45]([cH:46]2)[CH2:47][C@H:48]([NH:49][C:50](=[O:51])[O:52][C:53]([CH3:54])([CH3:55])[CH3:56])[C:57](=[O:58])[NH:59][C@@H:60]([CH2:61][CH2:62][CH2:63][NH:64][C:65](=[O:66])[O:67][C:68]([CH3:69])([CH3:70])[CH3:71])[C:72](=[O:73])[NH:74]1.On1nnc2ccccc21.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH2:11][C@@H:12]([CH2:13][NH:14][C:15](=[O:16])[C@H:17]([CH2:18][CH2:19][CH2:20][NH:21][C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[NH2:29])[NH:75][C:76](=[O:77])[O:78][C:79]([CH3:80])([CH3:81])[CH3:82] | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH2:11][C@@H:12]([CH2:13][NH:14][C:15](=[O:16])[C@H:17]([CH2:18][CH2:19][CH2:20][NH:21][C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[NH:29][C:30](=[O:31])[C@@H:32]1[CH2:33][c:34]2[cH:35][cH:36][cH:37][c:38]([cH:39]2)-[c:40]2[cH:41][cH:42][c:43]([OH:44])[c:45]([cH:46]2)[CH2:47][C@H:48]([NH:49][C:50](=[O:51])[O:52][C:53]([CH3:54])([CH3:55])[CH3:56])[C:57](=[O:58])[NH:59][C@@H:60]([CH2:61][CH2:62][CH2:63][NH:64][C:65](=[O:66])[O:67][C:68]([CH3:69])([CH3:70])[CH3:71])[C:72](=[O:73])[NH:74]1)[NH:75][C:76](=[O:77])[O:78][C:79]([CH3:80])([CH3:81])[CH3:82] | ([#7:5]-[C:6](=[O;D1;H0:7])-[C:8]-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4]).([#7:5]-[C:6](=[O;D1;H0:7])-[C:8]-[NH2;D1;+0:9]) | 858d3f6799b8d478063dc2653483f88126c5a9adf9a5b8705125d4e2 | 0.333333 | 3 | CN(C)C=O.ClCCCl.On1nnc2ccccc21 | 131 |
376,270 | 868,099 | null | C([N:8]1[CH2:13][CH2:12][C@@H:11]([CH3:14])[C@@H:10]([N:15]2[C:19]3=[C:20]4[CH:26]=[CH:25][NH:24][C:21]4=[N:22][CH:23]=[C:18]3[C:17]([NH:27][C:28](=[O:33])[C:29]([NH:31][CH3:32])=[O:30])=[N:16]2)[CH2:9]1)C1C=CC=CC=1.C(N1CC[C@H](C)[C@H](N2C3=C4C=CNC4=NC=C3C(NC(=O)C(NC)=O)=N2)C1)C1C=CC=CC=1>CCO.[OH-].[OH-].[Pd+2]>[CH3:32][NH:31][C:29](=[O:30])[C:28]([NH:27][C:17]1[C:18]2[C:19](=[C:20]3[CH:26]=[CH:25][NH:24][C:21]3=[N:22][CH:23]=2)[N:15]([C@@H:10]2[C@H:11]([CH3:14])[CH2:12][CH2:13][NH:8][CH2:9]2)[N:16]=1)=[O:33] | |f:3.4.5| | US20100105661A1_0301 | 2,010 | CCO.CNC(=O)C(=O)Nc1nn([C@H]2CN(Cc3ccccc3)CC[C@H]2C)c2c1cnc1[nH]ccc12.[OH-].[OH-].[Pd+2].c1ccc(C[N:13]2[CH2:12][C@@H:11]([n:10]3[n:9][c:8]([NH:7][C:5]([C:3]([NH:2][CH3:1])=[O:4])=[O:6])[c:19]4[c:18]3[c:26]3[c:22]([n:21][cH:20]4)[nH:23][cH:24][cH:25]3)[C@@H:16]([CH3:17])[CH2:15][CH2:14]2)cc1>>[CH3:1][NH:2][C:3](=[O:4])[C:5](=[O:6])[NH:7][c:8]1[n:9][n:10]([C@H:11]2[CH2:12][NH:13][CH2:14][CH2:15][C@H:16]2[CH3:17])[c:18]2[c:19]1[cH:20][n:21][c:22]1[nH:23][cH:24][cH:25][c:26]21 | 0.426253 | CCO.CNC(=O)C(=O)Nc1nn([C@@H]2CN(Cc3ccccc3)CC[C@@H]2C)c2c1cnc1[nH]ccc12.CNC(=O)C(=O)Nc1nn([C@H]2CN(Cc3ccccc3)CC[C@H]2C)c2c1cnc1[nH]ccc12.[OH-]~[OH-]~[Pd+2]>>CNC(=O)C(=O)Nc1nn([C@H]2CNCC[C@H]2C)c2c1cnc1[nH]ccc12 | CCO.CNC(=O)C(=O)Nc1nn([C@@H]2CN(Cc3ccccc3)CC[C@@H]2C)c2c1cnc1[nH]ccc12.CNC(=O)C(=O)Nc1nn([C@H]2CN(Cc3ccccc3)CC[C@H]2C)c2c1cnc1[nH]ccc12.[OH-].[OH-].[Pd+2]>>CNC(=O)C(=O)Nc1nn([C@H]2CNCC[C@H]2C)c2c1cnc1[nH]ccc12 | US20100105661A1_0301apps | f81e103ee45ab682cbae11e8175eba7a7921d11c1fb5df46bc8f626e | CCO.CNC(=O)C(=O)Nc1nn([C@H]2CN(Cc3ccccc3)CC[C@H]2C)c2c1cnc1[nH]ccc12.[OH-].[OH-].[Pd+2].c1ccc(C[N:13]2[CH2:12][C@@H:11]([n:10]3[n:9][c:8]([NH:7][C:5]([C:3]([NH:2][CH3:1])=[O:4])=[O:6])[c:19]4[c:18]3[c:26]3[c:22]([n:21][cH:20]4)[nH:23][cH:24][cH:25]3)[C@@H:16]([CH3:17])[CH2:15][CH2:14]2)cc1 | [CH3:1][NH:2][C:3](=[O:4])[C:5](=[O:6])[NH:7][c:8]1[n:9][n:10]([C@H:11]2[CH2:12][NH:13][CH2:14][CH2:15][C@H:16]2[CH3:17])[c:18]2[c:19]1[cH:20][n:21][c:22]1[nH:23][cH:24][cH:25][c:26]21 | ([C:1]-[NH;D2;+0:2]-[C:3])>>([C:1]-[N;H0;D3;+0:2](-[C:3])-C-c1:c:c:c:c:c:1) | f58207c6c64a5b48e40756ac3ba50fe69cdf9b1d18b6063ebd95ff15 | 0.5 | 2 | CCO.CNC(=O)C(=O)Nc1nn([C@H]2CN(Cc3ccccc3)CC[C@H]2C)c2c1cnc1[nH]ccc12.[OH-].[OH-].[Pd+2] | 84 |
42,854 | 189,053 | 304,331 | [CH:1]([C:4]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[N:5]=1)([CH3:3])[CH3:2].Br[CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].[I-].[Na+].C(OCC)(=O)C>CN(C)C=O>[C:18]([CH2:17][CH2:16][CH2:15][CH2:14][N:8]1[C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[N:5]=[C:4]1[CH:1]([CH3:3])[CH3:2])([O:20][CH2:21][CH3:22])=[O:19] | |f:2.3| | US05364875_ | 1,994 | Br[CH2:9][CH2:8][CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].CCOC(C)=O.CN(C)C=O.[I-].[Na+].[nH:10]1[c:11]([CH:12]([CH3:13])[CH3:14])[n:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]12>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH2:8][CH2:9][n:10]1[c:11]([CH:12]([CH3:13])[CH3:14])[n:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]12 | 0.820636 | CC(C)c1nc2ccccc2[nH]1.CCOC(=O)CCCCBr.CCOC(C)=O.CN(C)C=O.[I-]~[Na+]>>CCOC(=O)CCCCn1c(C(C)C)nc2ccccc21 | CC(C)c1nc2ccccc2[nH]1.CCOC(=O)CCCCBr.CCOC(C)=O.CN(C)C=O.[I-].[Na+]>>CCOC(=O)CCCCn1c(C(C)C)nc2ccccc21 | US05364875_grants | 9002c8cc67ced30a562808855e3a3b2e5808ba2a7947c3afe0741ff3 | Br[CH2:9][CH2:8][CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].CCOC(C)=O.CN(C)C=O.[I-].[Na+].[nH:10]1[c:11]([CH:12]([CH3:13])[CH3:14])[n:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]12 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH2:8][CH2:9][n:10]1[c:11]([CH:12]([CH3:13])[CH3:14])[n:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]12 | ([C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:5]1:[c:4]:[#7;a:3]:[c:7]:[c:6]:1)>>(Br-[CH2;D2;+0:1]-[C:2]).([#7;a:3]1:[c:4]:[nH;D2;+0:5]:[c:6]:[c:7]:1) | e6f82f99737957fd3d73a764ec35b21559f30f950090260f09e99f03 | 1 | 1 | CCOC(C)=O.CN(C)C=O.[I-].[Na+] | 276 |
204,914 | 696,482 | 1,147,273 | [F:1][C:2]1[CH:29]=[C:28]([N+:30]([O-])=O)[CH:27]=[CH:26][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[N:15]=[CH:16][N:17]([CH2:19][CH2:20][N:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)[CH:18]=3)[S:13][C:6]=12.[NH4+].[Cl-]>CCO.O.[Fe]>[F:1][C:2]1[CH:29]=[C:28]([CH:27]=[CH:26][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[N:15]=[CH:16][N:17]([CH2:19][CH2:20][N:21]4[CH2:22][CH2:23][CH2:24][CH2:25]4)[CH:18]=3)[S:13][C:6]=12)[NH2:30] | |f:1.2,3.4| | US08093264B2_0745 | 2,012 | CCO.O.O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[cH:8][cH:9][n:10][c:11]3[cH:12][c:13](-[c:14]4[cH:15][n:16]([CH2:17][CH2:18][N:19]5[CH2:20][CH2:21][CH2:22][CH2:23]5)[cH:24][n:25]4)[s:26][c:27]23)[c:28]([F:29])[cH:30]1.[Cl-].[Fe].[NH4+]>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[cH:8][cH:9][n:10][c:11]3[cH:12][c:13](-[c:14]4[cH:15][n:16]([CH2:17][CH2:18][N:19]5[CH2:20][CH2:21][CH2:22][CH2:23]5)[cH:24][n:25]4)[s:26][c:27]23)[c:28]([F:29])[cH:30]1 | 0.952464 | CCO~O.O=[N+]([O-])c1ccc(Oc2ccnc3cc(-c4cn(CCN5CCCC5)cn4)sc23)c(F)c1.[Cl-]~[NH4+].[Fe]>>Nc1ccc(Oc2ccnc3cc(-c4cn(CCN5CCCC5)cn4)sc23)c(F)c1 | CCO.O.O=[N+]([O-])c1ccc(Oc2ccnc3cc(-c4cn(CCN5CCCC5)cn4)sc23)c(F)c1.[Cl-].[Fe].[NH4+]>>Nc1ccc(Oc2ccnc3cc(-c4cn(CCN5CCCC5)cn4)sc23)c(F)c1 | US08093264B2_0745grants | 5c4e20376c2f88072e90b046901bfd66cf9221af9faa755cebee2ea0 | CCO.O.O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[cH:8][cH:9][n:10][c:11]3[cH:12][c:13](-[c:14]4[cH:15][n:16]([CH2:17][CH2:18][N:19]5[CH2:20][CH2:21][CH2:22][CH2:23]5)[cH:24][n:25]4)[s:26][c:27]23)[c:28]([F:29])[cH:30]1.[Cl-].[Fe].[NH4+] | [NH2:1][c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[cH:8][cH:9][n:10][c:11]3[cH:12][c:13](-[c:14]4[cH:15][n:16]([CH2:17][CH2:18][N:19]5[CH2:20][CH2:21][CH2:22][CH2:23]5)[cH:24][n:25]4)[s:26][c:27]23)[c:28]([F:29])[cH:30]1 | ([NH2;D1;+0:1]-[c:2]1:[c:3]:[c:4]:[c:5](-[#8:6]-[c:7]):[c:8]:[c:9]:1)>>(O=[N+;H0;D3:1](-[O-])-[c:2]1:[c:3]:[c:4]:[c:5](-[#8:6]-[c:7]):[c:8]:[c:9]:1) | 29ce6f8549b3eb39f0ff459e6dcee2e695f06f6055034d715c31e38e | 1 | 1 | CCO.O.[Cl-].[Fe].[NH4+] | 335 |
188,561 | 650,390 | 1,075,163 | [Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:39])[NH:7][C:8]([CH:12]([N:18]([C:30](=[O:38])[C:31]3[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=3)[CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:13]([N:15]([CH3:17])[CH3:16])=[O:14])=[N:9]2)=[CH:4][CH:3]=1.[CH3:40][C:41]1[CH:42]=[C:43]([CH:46]=[CH:47][CH:48]=1)[CH2:44]Br.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:39])[N:7]([CH2:40][C:41]3[CH:48]=[CH:47][CH:46]=[C:43]([CH3:44])[CH:42]=3)[C:8]([CH:12]([N:18]([C:30](=[O:38])[C:31]3[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=3)[CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:26])[CH3:27])[C:13]([N:15]([CH3:17])[CH3:16])=[O:14])=[N:9]2)=[CH:4][CH:3]=1 | |f:2.3.4| | US07939539B2_0322 | 2,011 | Br[CH2:38][c:39]1[cH:40][cH:41][cH:42][c:43]([CH3:44])[cH:45]1.CN(C)C=O.O.O=C([O-])[O-].[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[N:8]([CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH:20]([C:21](=[O:22])[N:23]([CH3:24])[CH3:25])[c:26]2[n:27][c:28]3[cH:29][c:30]([Cl:31])[cH:32][cH:33][c:34]3[c:35](=[O:36])[nH:37]2)[cH:46][cH:47]1.[K+].[K+]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[N:8]([CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH:20]([C:21](=[O:22])[N:23]([CH3:24])[CH3:25])[c:26]2[n:27][c:28]3[cH:29][c:30]([Cl:31])[cH:32][cH:33][c:34]3[c:35](=[O:36])[n:37]2[CH2:38][c:39]2[cH:40][cH:41][cH:42][c:43]([CH3:44])[cH:45]2)[cH:46][cH:47]1 | 0.296966 | CN(C)C=O.Cc1ccc(C(=O)N(CCCNC(=O)OC(C)(C)C)C(C(=O)N(C)C)c2nc3cc(Cl)ccc3c(=O)[nH]2)cc1.Cc1cccc(CBr)c1.O.O=C([O-])[O-]~[K+]~[K+]>>Cc1ccc(C(=O)N(CCCNC(=O)OC(C)(C)C)C(C(=O)N(C)C)c2nc3cc(Cl)ccc3c(=O)n2Cc2cccc(C)c2)cc1 | CN(C)C=O.Cc1ccc(C(=O)N(CCCNC(=O)OC(C)(C)C)C(C(=O)N(C)C)c2nc3cc(Cl)ccc3c(=O)[nH]2)cc1.Cc1cccc(CBr)c1.O.O=C([O-])[O-].[K+].[K+]>>Cc1ccc(C(=O)N(CCCNC(=O)OC(C)(C)C)C(C(=O)N(C)C)c2nc3cc(Cl)ccc3c(=O)n2Cc2cccc(C)c2)cc1 | US07939539B2_0322grants | cc253219892503be622a56be0c02366aac649d7b15dc37ce195a204f | Br[CH2:38][c:39]1[cH:40][cH:41][cH:42][c:43]([CH3:44])[cH:45]1.CN(C)C=O.O.O=C([O-])[O-].[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[N:8]([CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH:20]([C:21](=[O:22])[N:23]([CH3:24])[CH3:25])[c:26]2[n:27][c:28]3[cH:29][c:30]([Cl:31])[cH:32][cH:33][c:34]3[c:35](=[O:36])[nH:37]2)[cH:46][cH:47]1.[K+].[K+] | [CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[N:8]([CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH:20]([C:21](=[O:22])[N:23]([CH3:24])[CH3:25])[c:26]2[n:27][c:28]3[cH:29][c:30]([Cl:31])[cH:32][cH:33][c:34]3[c:35](=[O:36])[n:37]2[CH2:38][c:39]2[cH:40][cH:41][cH:42][c:43]([CH3:44])[cH:45]2)[cH:46][cH:47]1 | ([#7;a:3]:[c:4]:[n;H0;D3;+0:5](:[c:6])-[CH2;D2;+0:1]-[c:2])>>(Br-[CH2;D2;+0:1]-[c:2]).([#7;a:3]:[c:4]:[nH;D2;+0:5]:[c:6]) | 347f2f2c896bd34f8fcbc87d41072a5117d0aec0bf7c1b0b8bf92558 | 1 | 1 | CN(C)C=O.O.O=C([O-])[O-].[K+].[K+] | 389 |
352,027 | 505,949 | null | [Cl:1][C:2]1[C:3]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[N:4][CH:5]=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8].[N:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[C:20]=[O:21]>C(#N)C>[NH:19]([C:20]([N:16]1[CH2:17][CH2:18][N:13]([C:3]2[C:2]([Cl:1])=[CH:12][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:4]=2)[CH2:14][CH2:15]1)=[O:21])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1 | null | US20070244088A1_0439 | 2,007 | CC#N.[C:14](=[O:15])=[N:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([N:10]2[CH2:11][CH2:12][NH:13][CH2:23][CH2:24]2)[c:25]([Cl:26])[cH:27]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([N:10]2[CH2:11][CH2:12][N:13]([C:14](=[O:15])[NH:16][c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[CH2:23][CH2:24]2)[c:25]([Cl:26])[cH:27]1 | 0.876497 | CC#N.CCOC(=O)c1cnc(N2CCNCC2)c(Cl)c1.O=C=Nc1ccccc1>>CCOC(=O)c1cnc(N2CCN(C(=O)Nc3ccccc3)CC2)c(Cl)c1 | CC#N.CCOC(=O)c1cnc(N2CCNCC2)c(Cl)c1.O=C=Nc1ccccc1>>CCOC(=O)c1cnc(N2CCN(C(=O)Nc3ccccc3)CC2)c(Cl)c1 | US20070244088A1_0439apps | cb3673b9ccd46c4d4dc59063063adbe1b7f085857e8227146540f454 | CC#N.[C:14](=[O:15])=[N:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([N:10]2[CH2:11][CH2:12][NH:13][CH2:23][CH2:24]2)[c:25]([Cl:26])[cH:27]1 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([N:10]2[CH2:11][CH2:12][N:13]([C:14](=[O:15])[NH:16][c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[CH2:23][CH2:24]2)[c:25]([Cl:26])[cH:27]1 | ([C:1]-[N;H0;D3;+0:2](-[C:3])-[C;H0;D3;+0:5](=[O;D1;H0:4])-[NH;D2;+0:6]-[c:7])>>([C:1]-[NH;D2;+0:2]-[C:3]).([O;D1;H0:4]=[C;H0;D2;+0:5]=[N;H0;D2;+0:6]-[c:7]) | 09f63f034bbf4b29cbba07c3cfc12d8be3ce5a732a0a513d3a933b0e | 1 | 1 | CC#N | 323 |
193,758 | 665,891 | 1,101,005 | [NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[N:18]=[CH:17][C:16]3[C:11](=[CH:12][C:13]([C:19]([NH:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[O:20])=[CH:14][CH:15]=3)[N:10]=2)[CH2:4][CH2:3]1.[C:29](Cl)(=[O:31])[CH3:30].C(N(CC)CC)C.ClC(Cl)C.C(COC)OC>>[C:29]([NH:1][C@H:2]1[CH2:3][CH2:4][C@H:5]([NH:8][C:9]2[N:18]=[CH:17][C:16]3[C:11](=[CH:12][C:13]([C:19]([NH:21][CH2:22][C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)=[O:20])=[CH:14][CH:15]=3)[N:10]=2)[CH2:6][CH2:7]1)(=[O:31])[CH3:30] | |f:3.4| | US07998978B2_0359 | 2,011 | CC(Cl)Cl.CCN(CC)CC.COCCOC.Cl[C:2]([CH3:1])=[O:3].[NH2:4][C@H:5]1[CH2:6][CH2:7][C@H:8]([NH:9][c:10]2[n:11][cH:12][c:13]3[cH:14][cH:15][c:16]([C:17](=[O:18])[NH:19][CH2:20][c:21]4[cH:22][cH:23][cH:24][cH:25][cH:26]4)[cH:27][c:28]3[n:29]2)[CH2:30][CH2:31]1>>[CH3:1][C:2](=[O:3])[NH:4][C@H:5]1[CH2:6][CH2:7][C@H:8]([NH:9][c:10]2[n:11][cH:12][c:13]3[cH:14][cH:15][c:16]([C:17](=[O:18])[NH:19][CH2:20][c:21]4[cH:22][cH:23][cH:24][cH:25][cH:26]4)[cH:27][c:28]3[n:29]2)[CH2:30][CH2:31]1 | 0.880372 | CC(=O)Cl.CC(Cl)Cl~COCCOC.CCN(CC)CC.N[C@@H]1CC[C@@H](Nc2ncc3ccc(C(=O)NCc4ccccc4)cc3n2)CC1>>CC(=O)N[C@@H]1CC[C@@H](Nc2ncc3ccc(C(=O)NCc4ccccc4)cc3n2)CC1 | CC(=O)Cl.CC(Cl)Cl.CCN(CC)CC.COCCOC.N[C@@H]1CC[C@@H](Nc2ncc3ccc(C(=O)NCc4ccccc4)cc3n2)CC1>>CC(=O)N[C@@H]1CC[C@@H](Nc2ncc3ccc(C(=O)NCc4ccccc4)cc3n2)CC1 | US07998978B2_0359grants | 926d0b8749a1d32720adf04249f04eb0667454ca76da283a7e717bc5 | CC(Cl)Cl.CCN(CC)CC.COCCOC.Cl[C:2]([CH3:1])=[O:3].[NH2:4][C@H:5]1[CH2:6][CH2:7][C@H:8]([NH:9][c:10]2[n:11][cH:12][c:13]3[cH:14][cH:15][c:16]([C:17](=[O:18])[NH:19][CH2:20][c:21]4[cH:22][cH:23][cH:24][cH:25][cH:26]4)[cH:27][c:28]3[n:29]2)[CH2:30][CH2:31]1 | [CH3:1][C:2](=[O:3])[NH:4][C@H:5]1[CH2:6][CH2:7][C@H:8]([NH:9][c:10]2[n:11][cH:12][c:13]3[cH:14][cH:15][c:16]([C:17](=[O:18])[NH:19][CH2:20][c:21]4[cH:22][cH:23][cH:24][cH:25][cH:26]4)[cH:27][c:28]3[n:29]2)[CH2:30][CH2:31]1 | ([C:4]-[NH;D2;+0:5]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])>>(Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3]).([C:4]-[NH2;D1;+0:5]) | 493dfbb0afd083041fcf14557ee7dc8217381b2f2e0ce03b2961712e | 1 | 1 | CC(Cl)Cl.CCN(CC)CC.COCCOC | 45 |
330,292 | 80,447 | null | [CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11](F)[C:12]=3[CH3:14])[C:7](=[O:17])[NH:6][C:5]2=[O:18])[CH2:3][CH2:2]1.[C:19]([O:23][C:24](=[O:34])[NH:25][C:26]1([C@@H:29]2[CH2:33][CH2:32][NH:31][CH2:30]2)[CH2:28][CH2:27]1)([CH3:22])([CH3:21])[CH3:20].CN(C)C(N(C)C)=N.CS(C)=O>O>[C:19]([O:23][C:24](=[O:34])[NH:25][C:26]1([C@@H:29]2[CH2:33][CH2:32][N:31]([C:11]3[C:12]([CH3:14])=[C:13]4[C:8]([C:7](=[O:17])[NH:6][C:5](=[O:18])[N:4]4[CH:1]4[CH2:3][CH2:2]4)=[CH:9][C:10]=3[F:16])[CH2:30]2)[CH2:28][CH2:27]1)([CH3:22])([CH3:20])[CH3:21] | null | US20030114666A1_1903 | 2,003 | CN(C)C(=N)N(C)C.CS(C)=O.F[c:3]1[c:2]([CH3:1])[c:33]2[c:23]([cH:22][c:20]1[F:21])[c:24](=[O:25])[nH:26][c:27](=[O:28])[n:29]2[CH:30]1[CH2:31][CH2:32]1.O.[NH:4]1[CH2:5][CH2:6][C@@H:7]([C:8]2([NH:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[CH2:17][CH2:18]2)[CH2:19]1>>[CH3:1][c:2]1[c:3]([N:4]2[CH2:5][CH2:6][C@@H:7]([C:8]3([NH:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[CH2:17][CH2:18]3)[CH2:19]2)[c:20]([F:21])[cH:22][c:23]2[c:24](=[O:25])[nH:26][c:27](=[O:28])[n:29]([CH:30]3[CH2:31][CH2:32]3)[c:33]12 | 0.252094 | CC(C)(C)OC(=O)NC1([C@@H]2CCNC2)CC1.CN(C)C(=N)N(C)C.CS(C)=O.Cc1c(F)c(F)cc2c(=O)[nH]c(=O)n(C3CC3)c12.O>>Cc1c(N2CC[C@@H](C3(NC(=O)OC(C)(C)C)CC3)C2)c(F)cc2c(=O)[nH]c(=O)n(C3CC3)c12 | CC(C)(C)OC(=O)NC1([C@@H]2CCNC2)CC1.CN(C)C(=N)N(C)C.CS(C)=O.Cc1c(F)c(F)cc2c(=O)[nH]c(=O)n(C3CC3)c12.O>>Cc1c(N2CC[C@@H](C3(NC(=O)OC(C)(C)C)CC3)C2)c(F)cc2c(=O)[nH]c(=O)n(C3CC3)c12 | US20030114666A1_1903apps | 32fef547a168bdf5f6d35e3f0273557e6a1d84cc084828d77139d291 | CN(C)C(=N)N(C)C.CS(C)=O.F[c:3]1[c:2]([CH3:1])[c:33]2[c:23]([cH:22][c:20]1[F:21])[c:24](=[O:25])[nH:26][c:27](=[O:28])[n:29]2[CH:30]1[CH2:31][CH2:32]1.O.[NH:4]1[CH2:5][CH2:6][C@@H:7]([C:8]2([NH:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[CH2:17][CH2:18]2)[CH2:19]1 | [CH3:1][c:2]1[c:3]([N:4]2[CH2:5][CH2:6][C@@H:7]([C:8]3([NH:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[CH2:17][CH2:18]3)[CH2:19]2)[c:20]([F:21])[cH:22][c:23]2[c:24](=[O:25])[nH:26][c:27](=[O:28])[n:29]([CH:30]3[CH2:31][CH2:32]3)[c:33]12 | ([#7;a:5]:[c:4]:[c:3]:[c;H0;D3;+0:1](:[c:2])-[N;H0;D3;+0:7](-[C:6])-[C:8])>>(F-[c;H0;D3;+0:1](:[c:2]):[c:3]:[c:4]:[#7;a:5]).([C:6]-[NH;D2;+0:7]-[C:8]) | 38d86a3e11eae0b3218bf421862567dd26a714dac468bf4b7dab32ea | 1 | 1 | CN(C)C(=N)N(C)C.CS(C)=O.O | 676 |
27,727 | 128,829 | 207,879 | C(=O)([O-])[O-].[K+].[K+].[Br:7][CH2:8][CH2:9][CH2:10]Br.[C:12]1([SH:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CC(CC)=O>[Br:7][CH2:8][CH2:9][CH2:10][S:18][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1 | |f:0.1.2| | US04906658_ | 1,990 | Br[CH2:4][CH2:3][CH2:2][Br:1].CCC(C)=O.O=C([O-])[O-].[K+].[K+].[SH:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1>>[Br:1][CH2:2][CH2:3][CH2:4][S:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1 | 0.754436 | BrCCCBr.CCC(C)=O.O=C([O-])[O-]~[K+]~[K+].Sc1ccccc1>>BrCCCSc1ccccc1 | BrCCCBr.CCC(C)=O.O=C([O-])[O-].Sc1ccccc1.[K+].[K+]>>BrCCCSc1ccccc1 | US04906658_grants | 510e1f81ecafb404b06a5019c3180f67b42886b38d847cb9749eb0a5 | Br[CH2:4][CH2:3][CH2:2][Br:1].CCC(C)=O.O=C([O-])[O-].[K+].[K+].[SH:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1 | [Br:1][CH2:2][CH2:3][CH2:4][S:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1 | ([C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:3]-[c:4])>>(Br-[CH2;D2;+0:1]-[C:2]).([SH;D1;+0:3]-[c:4]) | b73d38e46252a190f18366e71c7fd160a59a139df9fb6551d999a041 | 1 | 1 | CCC(C)=O.O=C([O-])[O-].[K+].[K+] | 124 |
375,409 | 853,857 | null | [C:1]1([C:7]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH2:22][C@@H:23]4[CH2:28][CH2:27][CH2:26][NH:25][CH2:24]4)=[CH:17][CH:16]=3)[CH2:11][CH2:10]2)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:29][C:30]([CH3:32])=O>>[CH3:29][CH:30]([N:25]1[CH2:26][CH2:27][CH2:28][C@@H:23]([CH2:22][O:21][C:18]2[CH:19]=[CH:20][C:15]([N:12]3[CH2:13][CH2:14][N:9]([C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[O:8])[CH2:10][CH2:11]3)=[CH:16][CH:17]=2)[CH2:24]1)[CH3:32] | null | US20100075953A1_0321 | 2,010 | O=[C:2]([CH3:1])[CH3:3].[NH:4]1[CH2:5][CH2:6][CH2:7][C@@H:8]([CH2:9][O:10][c:11]2[cH:12][cH:13][c:14]([N:15]3[CH2:16][CH2:17][N:18]([C:19](=[O:20])[c:21]4[cH:22][cH:23][cH:24][cH:25][cH:26]4)[CH2:27][CH2:28]3)[cH:29][cH:30]2)[CH2:31]1>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH2:7][C@@H:8]([CH2:9][O:10][c:11]2[cH:12][cH:13][c:14]([N:15]3[CH2:16][CH2:17][N:18]([C:19](=[O:20])[c:21]4[cH:22][cH:23][cH:24][cH:25][cH:26]4)[CH2:27][CH2:28]3)[cH:29][cH:30]2)[CH2:31]1 | 0.598937 | CC(C)=O.O=C(c1ccccc1)N1CCN(c2ccc(OC[C@@H]3CCCNC3)cc2)CC1>>CC(C)N1CCC[C@@H](COc2ccc(N3CCN(C(=O)c4ccccc4)CC3)cc2)C1 | CC(C)=O.O=C(c1ccccc1)N1CCN(c2ccc(OC[C@@H]3CCCNC3)cc2)CC1>>CC(C)N1CCC[C@@H](COc2ccc(N3CCN(C(=O)c4ccccc4)CC3)cc2)C1 | US20100075953A1_0321apps | b3f5a3462dc5705e7cd7e4ece8b63f08883e7f2b6c6d9adb6ec78661 | O=[C:2]([CH3:1])[CH3:3].[NH:4]1[CH2:5][CH2:6][CH2:7][C@@H:8]([CH2:9][O:10][c:11]2[cH:12][cH:13][c:14]([N:15]3[CH2:16][CH2:17][N:18]([C:19](=[O:20])[c:21]4[cH:22][cH:23][cH:24][cH:25][cH:26]4)[CH2:27][CH2:28]3)[cH:29][cH:30]2)[CH2:31]1 | [CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH2:7][C@@H:8]([CH2:9][O:10][c:11]2[cH:12][cH:13][c:14]([N:15]3[CH2:16][CH2:17][N:18]([C:19](=[O:20])[c:21]4[cH:22][cH:23][cH:24][cH:25][cH:26]4)[CH2:27][CH2:28]3)[cH:29][cH:30]2)[CH2:31]1 | ([C:4]-[N;H0;D3;+0:5](-[C:6])-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3])>>(O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3]).([C:4]-[NH;D2;+0:5]-[C:6]) | f4afa1fa835dd5933ebafc736a3120b7569d6bf2160303a8812e2d2c | 1 | 1 | null | 187 |
120,671 | 447,639 | 760,344 | [NH2:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][C:7]2[NH:15][C:14]3[C:13](=[O:16])[N:12]([CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[F:24])[C:11](=[O:25])[N:10]([CH2:26][CH2:27][CH2:28][CH3:29])[C:9]=3[N:8]=2)=[CH:4][CH:3]=1.[Cl:32][C:33]1[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][C:34]=1[S:40](Cl)(=[O:42])=[O:41]>>[CH2:26]([N:10]1[C:9]2[N:8]=[C:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([NH:1][S:40]([C:34]4[CH:35]=[C:36]([Cl:39])[CH:37]=[CH:38][C:33]=4[Cl:32])(=[O:42])=[O:41])=[CH:31][CH:30]=3)[NH:15][C:14]=2[C:13](=[O:16])[N:12]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[F:24])[C:11]1=[O:25])[CH2:27][CH2:28][CH3:29] | null | US07148229B2_0458 | 2,006 | Cl[S:28](=[O:29])(=[O:30])[c:31]1[cH:32][c:33]([Cl:34])[cH:35][cH:36][c:37]1[Cl:38].[CH3:1][CH2:2][CH2:3][CH2:4][n:5]1[c:6](=[O:7])[n:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[F:16])[c:17](=[O:18])[c:19]2[nH:20][c:21]([CH2:22][c:23]3[cH:24][cH:25][c:26]([NH2:27])[cH:39][cH:40]3)[n:41][c:42]12>>[CH3:1][CH2:2][CH2:3][CH2:4][n:5]1[c:6](=[O:7])[n:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[F:16])[c:17](=[O:18])[c:19]2[nH:20][c:21]([CH2:22][c:23]3[cH:24][cH:25][c:26]([NH:27][S:28](=[O:29])(=[O:30])[c:31]4[cH:32][c:33]([Cl:34])[cH:35][cH:36][c:37]4[Cl:38])[cH:39][cH:40]3)[n:41][c:42]12 | 0.689717 | CCCCn1c(=O)n(Cc2ccccc2F)c(=O)c2[nH]c(Cc3ccc(N)cc3)nc21.O=S(=O)(Cl)c1cc(Cl)ccc1Cl>>CCCCn1c(=O)n(Cc2ccccc2F)c(=O)c2[nH]c(Cc3ccc(NS(=O)(=O)c4cc(Cl)ccc4Cl)cc3)nc21 | CCCCn1c(=O)n(Cc2ccccc2F)c(=O)c2[nH]c(Cc3ccc(N)cc3)nc21.O=S(=O)(Cl)c1cc(Cl)ccc1Cl>>CCCCn1c(=O)n(Cc2ccccc2F)c(=O)c2[nH]c(Cc3ccc(NS(=O)(=O)c4cc(Cl)ccc4Cl)cc3)nc21 | US07148229B2_0458grants | edebb9339f4c51bf98c9e10f340e4ac264f5a639f6ae7963c4ad2edc | Cl[S:28](=[O:29])(=[O:30])[c:31]1[cH:32][c:33]([Cl:34])[cH:35][cH:36][c:37]1[Cl:38].[CH3:1][CH2:2][CH2:3][CH2:4][n:5]1[c:6](=[O:7])[n:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[F:16])[c:17](=[O:18])[c:19]2[nH:20][c:21]([CH2:22][c:23]3[cH:24][cH:25][c:26]([NH2:27])[cH:39][cH:40]3)[n:41][c:42]12 | [CH3:1][CH2:2][CH2:3][CH2:4][n:5]1[c:6](=[O:7])[n:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[F:16])[c:17](=[O:18])[c:19]2[nH:20][c:21]([CH2:22][c:23]3[cH:24][cH:25][c:26]([NH:27][S:28](=[O:29])(=[O:30])[c:31]4[cH:32][c:33]([Cl:34])[cH:35][cH:36][c:37]4[Cl:38])[cH:39][cH:40]3)[n:41][c:42]12 | ([O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[c:4])-[NH;D2;+0:5]-[c:6])>>(Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4]).([NH2;D1;+0:5]-[c:6]) | 5e78a661181f8271dd0d21f0efa96b7d75105c87fa022f79effe5902 | 1 | 1 | null | 68 |
444,943 | 1,938,671 | null | [C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:10]([O:14][C:15](=[O:49])[N:16]([C@H:18]([C:20](=[O:48])[NH:21][C@@H:22]1[C:28](=[O:29])[N:27]([CH2:30][C:31]2[C:40]3[C:35](=[CH:36][C:37]([Br:41])=[CH:38][CH:39]=3)[CH:34]=[CH:33][C:32]=2[O:42][CH3:43])[C:26]2[CH:44]=[CH:45][CH:46]=[CH:47][C:25]=2[NH:24][CH2:23]1)[CH3:19])[CH3:17])([CH3:13])([CH3:12])[CH3:11].N1C=CC=CC=1>C(Cl)Cl>[C:10]([O:14][C:15](=[O:49])[N:16]([C@H:18]([C:20](=[O:48])[NH:21][C@@H:22]1[C:28](=[O:29])[N:27]([CH2:30][C:31]2[C:40]3[C:35](=[CH:36][C:37]([Br:41])=[CH:38][CH:39]=3)[CH:34]=[CH:33][C:32]=2[O:42][CH3:43])[C:26]2[CH:44]=[CH:45][CH:46]=[CH:47][C:25]=2[N:24]([C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:23]1)[CH3:19])[CH3:17])([CH3:11])([CH3:12])[CH3:13] | null | US20160272596A1_1386 | 2,016 | ClCCl.Cl[C:35](=[O:36])[c:37]1[cH:38][cH:39][cH:40][cH:41][cH:42]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][c:8]([Br:9])[cH:10][cH:11][c:12]2[c:13]1[CH2:14][N:15]1[C:16](=[O:17])[C@@H:18]([NH:19][C:20](=[O:21])[C@H:22]([CH3:23])[N:24]([CH3:25])[C:26](=[O:27])[O:28][C:29]([CH3:30])([CH3:31])[CH3:32])[CH2:33][NH:34][c:43]2[cH:44][cH:45][cH:46][cH:47][c:48]21.c1ccncc1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][c:8]([Br:9])[cH:10][cH:11][c:12]2[c:13]1[CH2:14][N:15]1[C:16](=[O:17])[C@@H:18]([NH:19][C:20](=[O:21])[C@H:22]([CH3:23])[N:24]([CH3:25])[C:26](=[O:27])[O:28][C:29]([CH3:30])([CH3:31])[CH3:32])[CH2:33][N:34]([C:35](=[O:36])[c:37]2[cH:38][cH:39][cH:40][cH:41][cH:42]2)[c:43]2[cH:44][cH:45][cH:46][cH:47][c:48]21 | 0.416695 | COc1ccc2cc(Br)ccc2c1CN1C(=O)[C@@H](NC(=O)[C@H](C)N(C)C(=O)OC(C)(C)C)CNc2ccccc21.ClCCl.O=C(Cl)c1ccccc1.c1ccncc1>>COc1ccc2cc(Br)ccc2c1CN1C(=O)[C@@H](NC(=O)[C@H](C)N(C)C(=O)OC(C)(C)C)CN(C(=O)c2ccccc2)c2ccccc21 | COc1ccc2cc(Br)ccc2c1CN1C(=O)[C@@H](NC(=O)[C@H](C)N(C)C(=O)OC(C)(C)C)CNc2ccccc21.ClCCl.O=C(Cl)c1ccccc1.c1ccncc1>>COc1ccc2cc(Br)ccc2c1CN1C(=O)[C@@H](NC(=O)[C@H](C)N(C)C(=O)OC(C)(C)C)CN(C(=O)c2ccccc2)c2ccccc21 | US20160272596A1_1386apps | b914ba060d9da6298056bedee243152316e86d30448104afd6907d94 | ClCCl.Cl[C:35](=[O:36])[c:37]1[cH:38][cH:39][cH:40][cH:41][cH:42]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][c:8]([Br:9])[cH:10][cH:11][c:12]2[c:13]1[CH2:14][N:15]1[C:16](=[O:17])[C@@H:18]([NH:19][C:20](=[O:21])[C@H:22]([CH3:23])[N:24]([CH3:25])[C:26](=[O:27])[O:28][C:29]([CH3:30])([CH3:31])[CH3:32])[CH2:33][NH:34][c:43]2[cH:44][cH:45][cH:46][cH:47][c:48]21.c1ccncc1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][c:8]([Br:9])[cH:10][cH:11][c:12]2[c:13]1[CH2:14][N:15]1[C:16](=[O:17])[C@@H:18]([NH:19][C:20](=[O:21])[C@H:22]([CH3:23])[N:24]([CH3:25])[C:26](=[O:27])[O:28][C:29]([CH3:30])([CH3:31])[CH3:32])[CH2:33][N:34]([C:35](=[O:36])[c:37]2[cH:38][cH:39][cH:40][cH:41][cH:42]2)[c:43]2[cH:44][cH:45][cH:46][cH:47][c:48]21 | ([C:4]-[N;H0;D3;+0:5](-[c:6])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3])>>(Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]).([C:4]-[NH;D2;+0:5]-[c:6]) | 3a1fd98266c56170b70ca1ddbad79f42c7bbe8f5d5f0da8c7b389a8b | 1 | 1 | ClCCl.c1ccncc1 | 614 |
93,237 | 364,852 | 622,551 | [CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10](/[CH:13]=[CH:14]/[C:15]([OH:17])=O)[S:11][CH:12]=2)=[CH:4][CH:3]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.Cl.Cl.[CH3:42][N:43]([CH2:50][C@H:51]1[CH2:56][CH2:55][C@H:54]([NH2:57])[CH2:53][CH2:52]1)[CH:44]1[CH2:49][CH2:48][O:47][CH2:46][CH2:45]1.C1CCN2C(=NCCC2)CC1>C(#N)C.C(N(CC)CC)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10](/[CH:13]=[CH:14]/[C:15]([NH:57][C@H:54]3[CH2:53][CH2:52][C@H:51]([CH2:50][N:43]([CH3:42])[CH:44]4[CH2:49][CH2:48][O:47][CH2:46][CH2:45]4)[CH2:56][CH2:55]3)=[O:17])[S:11][CH:12]=2)=[CH:6][CH:7]=1 | |f:2.3,4.5.6| | US06627651B1_ | 2,003 | C1CCC2=NCCCN2CC1.CC#N.CCN(CC)CC.CCN=C=NCCCN(C)C.Cl.Cl.Cl.O[C:12](/[CH:11]=[CH:10]/[c:9]1[s:8][cH:7][c:6](-[c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:32][cH:31]2)[cH:30]1)=[O:13].On1nnc2ccccc21.[NH2:14][C@H:15]1[CH2:16][CH2:17][C@H:18]([CH2:19][N:20]([CH3:21])[CH:22]2[CH2:23][CH2:24][O:25][CH2:26][CH2:27]2)[CH2:28][CH2:29]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][s:8][c:9](/[CH:10]=[CH:11]/[C:12](=[O:13])[NH:14][C@H:15]3[CH2:16][CH2:17][C@H:18]([CH2:19][N:20]([CH3:21])[CH:22]4[CH2:23][CH2:24][O:25][CH2:26][CH2:27]4)[CH2:28][CH2:29]3)[cH:30]2)[cH:31][cH:32]1 | 0.822414 | C1CCC2=NCCCN2CC1.CC#N.CCN(CC)CC.CCN=C=NCCCN(C)C~Cl.CN(C[C@@H]1CC[C@@H](N)CC1)C1CCOCC1~Cl~Cl.Cc1ccc(-c2csc(/C=C/C(=O)O)c2)cc1.On1nnc2ccccc21>>Cc1ccc(-c2csc(/C=C/C(=O)N[C@@H]3CC[C@@H](CN(C)C4CCOCC4)CC3)c2)cc1 | C1CCC2=NCCCN2CC1.CC#N.CCN(CC)CC.CCN=C=NCCCN(C)C.CN(C[C@@H]1CC[C@@H](N)CC1)C1CCOCC1.Cc1ccc(-c2csc(/C=C/C(=O)O)c2)cc1.Cl.Cl.Cl.On1nnc2ccccc21>>Cc1ccc(-c2csc(/C=C/C(=O)N[C@@H]3CC[C@@H](CN(C)C4CCOCC4)CC3)c2)cc1 | US06627651B1_grants | 9136c2158e6451c58ebe7c3a39c1cc70b441b21f69dbf95dac323b9a | C1CCC2=NCCCN2CC1.CC#N.CCN(CC)CC.CCN=C=NCCCN(C)C.Cl.Cl.Cl.O[C:12](/[CH:11]=[CH:10]/[c:9]1[s:8][cH:7][c:6](-[c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:32][cH:31]2)[cH:30]1)=[O:13].On1nnc2ccccc21.[NH2:14][C@H:15]1[CH2:16][CH2:17][C@H:18]([CH2:19][N:20]([CH3:21])[CH:22]2[CH2:23][CH2:24][O:25][CH2:26][CH2:27]2)[CH2:28][CH2:29]1 | [CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][s:8][c:9](/[CH:10]=[CH:11]/[C:12](=[O:13])[NH:14][C@H:15]3[CH2:16][CH2:17][C@H:18]([CH2:19][N:20]([CH3:21])[CH:22]4[CH2:23][CH2:24][O:25][CH2:26][CH2:27]4)[CH2:28][CH2:29]3)[cH:30]2)[cH:31][cH:32]1 | ([C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])/[C:3]=[C:4]/[c:5])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])/[C:3]=[C:4]/[c:5]).([C:6]-[NH2;D1;+0:7]) | db3a97a0f595e9e42a12f3453ea056a3bcdbffe0b03ec342281970dd | 1 | 1 | C1CCC2=NCCCN2CC1.CC#N.CCN(CC)CC.CCN=C=NCCCN(C)C.Cl.Cl.Cl.On1nnc2ccccc21 | 767 |
364,160 | 670,750 | null | [NH2:1][C:2]1[S:3][C:4]([C:13]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH3:24])=[CH:17][CH:16]=2)=[O:14])=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.[CH2:25]([O:27][C:28]1[C:33]([O:34][CH2:35][CH3:36])=[CH:32][C:31]([C:37](=[O:43])[CH2:38][CH2:39][C:40](O)=[O:41])=[C:30]([CH3:44])[CH:29]=1)[CH3:26].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C(#N)C>[CH2:21]([C:18]1[CH:17]=[CH:16][C:15]([C:13]([C:4]2[S:3][C:2]([NH:1][C:40](=[O:41])[CH2:39][CH2:38][C:37]([C:31]3[CH:32]=[C:33]([O:34][CH2:35][CH3:36])[C:28]([O:27][CH2:25][CH3:26])=[CH:29][C:30]=3[CH3:44])=[O:43])=[N:6][C:5]=2[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[O:14])=[CH:20][CH:19]=1)[CH2:22][CH2:23][CH3:24] | null | US20090048258A1_1267 | 2,009 | CC#N.CCN=C=NCCCN(C)C.O[C:15](=[O:16])[CH2:17][CH2:18][C:19](=[O:20])[c:21]1[cH:22][c:23]([O:24][CH2:25][CH3:26])[c:27]([O:28][CH2:29][CH3:30])[cH:31][c:32]1[CH3:33].On1nnc2ccccc21.[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[c:11]2[s:12][c:13]([NH2:14])[n:34][c:35]2-[c:36]2[cH:37][cH:38][cH:39][cH:40][cH:41]2)[cH:42][cH:43]1>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[c:11]2[s:12][c:13]([NH:14][C:15](=[O:16])[CH2:17][CH2:18][C:19](=[O:20])[c:21]3[cH:22][c:23]([O:24][CH2:25][CH3:26])[c:27]([O:28][CH2:29][CH3:30])[cH:31][c:32]3[CH3:33])[n:34][c:35]2-[c:36]2[cH:37][cH:38][cH:39][cH:40][cH:41]2)[cH:42][cH:43]1 | 0.803252 | CC#N.CCCCc1ccc(C(=O)c2sc(N)nc2-c2ccccc2)cc1.CCN=C=NCCCN(C)C.CCOc1cc(C)c(C(=O)CCC(=O)O)cc1OCC.On1nnc2ccccc21>>CCCCc1ccc(C(=O)c2sc(NC(=O)CCC(=O)c3cc(OCC)c(OCC)cc3C)nc2-c2ccccc2)cc1 | CC#N.CCCCc1ccc(C(=O)c2sc(N)nc2-c2ccccc2)cc1.CCN=C=NCCCN(C)C.CCOc1cc(C)c(C(=O)CCC(=O)O)cc1OCC.On1nnc2ccccc21>>CCCCc1ccc(C(=O)c2sc(NC(=O)CCC(=O)c3cc(OCC)c(OCC)cc3C)nc2-c2ccccc2)cc1 | US20090048258A1_1267apps | a5a03d5b8c23c4cbce89875407c3b23a275b9d1f9b8026360615e367 | CC#N.CCN=C=NCCCN(C)C.O[C:15](=[O:16])[CH2:17][CH2:18][C:19](=[O:20])[c:21]1[cH:22][c:23]([O:24][CH2:25][CH3:26])[c:27]([O:28][CH2:29][CH3:30])[cH:31][c:32]1[CH3:33].On1nnc2ccccc21.[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[c:11]2[s:12][c:13]([NH2:14])[n:34][c:35]2-[c:36]2[cH:37][cH:38][cH:39][cH:40][cH:41]2)[cH:42][cH:43]1 | [CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[c:11]2[s:12][c:13]([NH:14][C:15](=[O:16])[CH2:17][CH2:18][C:19](=[O:20])[c:21]3[cH:22][c:23]([O:24][CH2:25][CH3:26])[c:27]([O:28][CH2:29][CH3:30])[cH:31][c:32]3[CH3:33])[n:34][c:35]2-[c:36]2[cH:37][cH:38][cH:39][cH:40][cH:41]2)[cH:42][cH:43]1 | ([#16;a:4]:[c:5](:[#7;a:6])-[NH;D2;+0:7]-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3])>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([#16;a:4]:[c:5](:[#7;a:6])-[NH2;D1;+0:7]) | 1915f560d2e2ae3d3a4749f874a47ece1ab8982b05cac2f711ea52be | 1 | 1 | CC#N.CCN=C=NCCCN(C)C.On1nnc2ccccc21 | 681 |
111,205 | 418,279 | 712,845 | [H-].[Na+].[CH3:3][O:4][CH2:5][CH2:6][O:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]([CH2:16][OH:17])[CH:13]=[CH:14][CH:15]=1.Cl[C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=1>CS(C)=O.CCOC(C)=O>[CH3:3][O:4][CH2:5][CH2:6][O:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]([CH:13]=[CH:14][CH:15]=1)[CH2:16][O:17][C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=1 | |f:0.1| | US07005440B1_0838 | 2,006 | CCOC(C)=O.CS(C)=O.Cl[c:15]1[cH:16][cH:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]2[n:24]1.[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][c:8]1[cH:9][cH:10][cH:11][c:12]([CH2:13][OH:14])[cH:25]1.[H-].[Na+]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][c:8]1[cH:9][cH:10][cH:11][c:12]([CH2:13][O:14][c:15]2[cH:16][cH:17][c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]3[n:24]2)[cH:25]1 | 0.971673 | CCOC(C)=O.COCCOCOc1cccc(CO)c1.CS(C)=O.Clc1ccc2ccccc2n1.[H-]~[Na+]>>COCCOCOc1cccc(COc2ccc3ccccc3n2)c1 | CCOC(C)=O.COCCOCOc1cccc(CO)c1.CS(C)=O.Clc1ccc2ccccc2n1.[H-].[Na+]>>COCCOCOc1cccc(COc2ccc3ccccc3n2)c1 | US07005440B1_0838grants | 4e46ace64aaab6c419d55f106dc9afce176f829bd79d723913993c3c | CCOC(C)=O.CS(C)=O.Cl[c:15]1[cH:16][cH:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]2[n:24]1.[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][c:8]1[cH:9][cH:10][cH:11][c:12]([CH2:13][OH:14])[cH:25]1.[H-].[Na+] | [CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][c:8]1[cH:9][cH:10][cH:11][c:12]([CH2:13][O:14][c:15]2[cH:16][cH:17][c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]3[n:24]2)[cH:25]1 | ([#7;a:2]:[c;H0;D3;+0:1](:[c:3])-[O;H0;D2;+0:5]-[C:4])>>(Cl-[c;H0;D3;+0:1](:[#7;a:2]):[c:3]).([C:4]-[OH;D1;+0:5]) | 10907cd3c67b89554bc459401febf504bb2680a0918b9d386f58414c | 1 | 1 | CCOC(C)=O.CS(C)=O.[H-].[Na+] | 433 |
238,912 | 797,208 | 1,319,299 | [CH:1]1([CH:7]([NH:19][C:20]2[N:25]=[CH:24][C:23]([C:26]([O:28]C)=[O:27])=[CH:22][CH:21]=2)[C:8]2[O:9][C:10]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:11]=3[C:12]=2[CH3:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)C.[OH-].[Na+]>O1CCCC1>[CH:1]1([CH:7]([NH:19][C:20]2[N:25]=[CH:24][C:23]([C:26]([OH:28])=[O:27])=[CH:22][CH:21]=2)[C:8]2[O:9][C:10]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:11]=3[C:12]=2[CH3:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1 | |f:2.3| | US08436043B2_1577 | 2,013 | C1CCOC1.CCO.C[O:12][C:10]([c:9]1[cH:8][cH:7][c:6]([NH:5][CH:4]([c:3]2[c:2]([CH3:1])[c:28]3[c:22]([o:21]2)[cH:23][cH:24][c:25]([F:26])[cH:27]3)[CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]2)[n:14][cH:13]1)=[O:11].[Na+].[OH-]>>[CH3:1][c:2]1[c:3]([CH:4]([NH:5][c:6]2[cH:7][cH:8][c:9]([C:10](=[O:11])[OH:12])[cH:13][n:14]2)[CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]2)[o:21][c:22]2[cH:23][cH:24][c:25]([F:26])[cH:27][c:28]12 | 0.904096 | C1CCOC1.CCO.COC(=O)c1ccc(NC(c2oc3ccc(F)cc3c2C)C2CCCCC2)nc1.[Na+]~[OH-]>>Cc1c(C(Nc2ccc(C(=O)O)cn2)C2CCCCC2)oc2ccc(F)cc12 | C1CCOC1.CCO.COC(=O)c1ccc(NC(c2oc3ccc(F)cc3c2C)C2CCCCC2)nc1.[Na+].[OH-]>>Cc1c(C(Nc2ccc(C(=O)O)cn2)C2CCCCC2)oc2ccc(F)cc12 | US08436043B2_1577grants | 5d62c80e281207b48b005019f54d790bd1093fc49925a050c5c2baea | C1CCOC1.CCO.C[O:12][C:10]([c:9]1[cH:8][cH:7][c:6]([NH:5][CH:4]([c:3]2[c:2]([CH3:1])[c:28]3[c:22]([o:21]2)[cH:23][cH:24][c:25]([F:26])[cH:27]3)[CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]2)[n:14][cH:13]1)=[O:11].[Na+].[OH-] | [CH3:1][c:2]1[c:3]([CH:4]([NH:5][c:6]2[cH:7][cH:8][c:9]([C:10](=[O:11])[OH:12])[cH:13][n:14]2)[CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]2)[o:21][c:22]2[cH:23][cH:24][c:25]([F:26])[cH:27][c:28]12 | ([O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4])>>(C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]) | b499e0b68ab8cc89df665c73ba592c6e17427fbd5b75a0a04b8fb5db | 1 | 1 | C1CCOC1.CCO.[Na+].[OH-] | 152 |
102,832 | 393,738 | 672,886 | CS(C)=O.C(Cl)(=O)C(Cl)=O.N#N.[CH3:13][N:14]([C:18]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:15][CH2:16][OH:17].C(N(CC)CC)C>C(Cl)Cl>[CH3:13][N:14]([CH2:15][CH:16]=[O:17])[C:18]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1 | null | US06852731B2_01049 | 2,005 | CCN(CC)CC.CS(C)=O.ClCCl.N#N.O=C(Cl)C(=O)Cl.[CH3:1][N:2]([CH2:3][CH2:4][OH:5])[C:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)([c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1>>[CH3:1][N:2]([CH2:3][CH:4]=[O:5])[C:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)([c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1 | 0.34386 | CCN(CC)CC.CN(CCO)C(c1ccccc1)(c1ccccc1)c1ccccc1.CS(C)=O.ClCCl.N#N.O=C(Cl)C(=O)Cl>>CN(CC=O)C(c1ccccc1)(c1ccccc1)c1ccccc1 | CCN(CC)CC.CN(CCO)C(c1ccccc1)(c1ccccc1)c1ccccc1.CS(C)=O.ClCCl.N#N.O=C(Cl)C(=O)Cl>>CN(CC=O)C(c1ccccc1)(c1ccccc1)c1ccccc1 | US06852731B2_01049grants | 1bb98d6d8a0599b6353b51f32e243032b3f835c6b7952f96cc3e32c9 | CCN(CC)CC.CS(C)=O.ClCCl.N#N.O=C(Cl)C(=O)Cl.[CH3:1][N:2]([CH2:3][CH2:4][OH:5])[C:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)([c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1 | [CH3:1][N:2]([CH2:3][CH:4]=[O:5])[C:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)([c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1 | ([C:1]-[CH;D2;+0:2]=[O;H0;D1;+0:3])>>([C:1]-[CH2;D2;+0:2]-[OH;D1;+0:3]) | 61df3886a0291f08a9e9f8293588d04d916daa376a54f86534b439c2 | 1 | 1 | CCN(CC)CC.CS(C)=O.ClCCl.N#N.O=C(Cl)C(=O)Cl | 142 |
386,602 | 1,050,352 | null | [F:1][C:2]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:3]=1[CH2:4][N:5]1[C:10](=[O:11])[CH:9]=[CH:8][C:7]([CH2:12][C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([F:22])[CH:20]=3)[N:15]([CH2:23][C:24]([O:26]C)=[O:25])[C:14]=2[CH3:28])=[CH:6]1.O.[OH-].[Li+]>>[F:1][C:2]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:3]=1[CH2:4][N:5]1[C:10](=[O:11])[CH:9]=[CH:8][C:7]([CH2:12][C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([F:22])[CH:20]=3)[N:15]([CH2:23][C:24]([OH:26])=[O:25])[C:14]=2[CH3:28])=[CH:6]1 | |f:1.2.3| | US20110105509A1_0594 | 2,011 | C[O:32][C:30]([CH2:29][n:28]1[c:2]([CH3:1])[c:3]([CH2:4][c:5]2[cH:6][cH:7][c:8](=[O:9])[n:10]([CH2:11][c:12]3[cH:13][c:14]([F:15])[cH:16][cH:17][c:18]3[F:19])[cH:20]2)[c:21]2[cH:22][c:23]([F:24])[cH:25][cH:26][c:27]21)=[O:31].O.[Li+].[OH-]>>[CH3:1][c:2]1[c:3]([CH2:4][c:5]2[cH:6][cH:7][c:8](=[O:9])[n:10]([CH2:11][c:12]3[cH:13][c:14]([F:15])[cH:16][cH:17][c:18]3[F:19])[cH:20]2)[c:21]2[cH:22][c:23]([F:24])[cH:25][cH:26][c:27]2[n:28]1[CH2:29][C:30](=[O:31])[OH:32] | 0.957778 | COC(=O)Cn1c(C)c(Cc2ccc(=O)n(Cc3cc(F)ccc3F)c2)c2cc(F)ccc21.O~[Li+]~[OH-]>>Cc1c(Cc2ccc(=O)n(Cc3cc(F)ccc3F)c2)c2cc(F)ccc2n1CC(=O)O | COC(=O)Cn1c(C)c(Cc2ccc(=O)n(Cc3cc(F)ccc3F)c2)c2cc(F)ccc21.O.[Li+].[OH-]>>Cc1c(Cc2ccc(=O)n(Cc3cc(F)ccc3F)c2)c2cc(F)ccc2n1CC(=O)O | US20110105509A1_0594apps | a3bcc7b20876fcceaa63d6392cf0f53d9a611083a92a21873e372db9 | C[O:32][C:30]([CH2:29][n:28]1[c:2]([CH3:1])[c:3]([CH2:4][c:5]2[cH:6][cH:7][c:8](=[O:9])[n:10]([CH2:11][c:12]3[cH:13][c:14]([F:15])[cH:16][cH:17][c:18]3[F:19])[cH:20]2)[c:21]2[cH:22][c:23]([F:24])[cH:25][cH:26][c:27]21)=[O:31].O.[Li+].[OH-] | [CH3:1][c:2]1[c:3]([CH2:4][c:5]2[cH:6][cH:7][c:8](=[O:9])[n:10]([CH2:11][c:12]3[cH:13][c:14]([F:15])[cH:16][cH:17][c:18]3[F:19])[cH:20]2)[c:21]2[cH:22][c:23]([F:24])[cH:25][cH:26][c:27]2[n:28]1[CH2:29][C:30](=[O:31])[OH:32] | ([C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1])>>(C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]) | 0a02d2d47df007d05d29f7b852c5bfe9dcbd7a32224d027cc636bd27 | 1 | 1 | O.[Li+].[OH-] | 88 |
87,792 | 348,780 | 594,624 | O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][S:15]([C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:27])[CH3:26])=[CH:20][CH:19]=3)(=[O:17])=[O:16])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[NH2:28][CH2:29][CH:30]([C:32]1[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][C:33]=1[OH:39])[OH:31]>>[OH:39][C:33]1[CH:34]=[C:35]([OH:38])[CH:36]=[CH:37][C:32]=1[CH:30]([OH:31])[CH2:29][NH:28][CH:2]1[CH2:3][CH2:4][N:5]([C:8]2[CH:9]=[CH:10][C:11]([NH:14][S:15]([C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:27])[CH3:26])=[CH:20][CH:19]=3)(=[O:16])=[O:17])=[CH:12][CH:13]=2)[CH2:6][CH2:7]1 | null | US06525202B2_ | 2,003 | O=[C:20]1[CH2:19][CH2:18][N:17]([c:16]2[cH:15][cH:14][c:13]([NH:12][S:9]([c:8]3[cH:7][cH:6][c:5]([NH:4][C:2]([CH3:1])=[O:3])[cH:38][cH:37]3)(=[O:10])=[O:11])[cH:36][cH:35]2)[CH2:34][CH2:33]1.[NH2:21][CH2:22][CH:23]([OH:24])[c:25]1[cH:26][cH:27][c:28]([OH:29])[cH:30][c:31]1[OH:32]>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([S:9](=[O:10])(=[O:11])[NH:12][c:13]2[cH:14][cH:15][c:16]([N:17]3[CH2:18][CH2:19][CH:20]([NH:21][CH2:22][CH:23]([OH:24])[c:25]4[cH:26][cH:27][c:28]([OH:29])[cH:30][c:31]4[OH:32])[CH2:33][CH2:34]3)[cH:35][cH:36]2)[cH:37][cH:38]1 | 0.520302 | CC(=O)Nc1ccc(S(=O)(=O)Nc2ccc(N3CCC(=O)CC3)cc2)cc1.NCC(O)c1ccc(O)cc1O>>CC(=O)Nc1ccc(S(=O)(=O)Nc2ccc(N3CCC(NCC(O)c4ccc(O)cc4O)CC3)cc2)cc1 | CC(=O)Nc1ccc(S(=O)(=O)Nc2ccc(N3CCC(=O)CC3)cc2)cc1.NCC(O)c1ccc(O)cc1O>>CC(=O)Nc1ccc(S(=O)(=O)Nc2ccc(N3CCC(NCC(O)c4ccc(O)cc4O)CC3)cc2)cc1 | US06525202B2_grants | 07816351a36ae0a6a4a149b1c2d224ef93fd009ec7f1520316e3151b | O=[C:20]1[CH2:19][CH2:18][N:17]([c:16]2[cH:15][cH:14][c:13]([NH:12][S:9]([c:8]3[cH:7][cH:6][c:5]([NH:4][C:2]([CH3:1])=[O:3])[cH:38][cH:37]3)(=[O:10])=[O:11])[cH:36][cH:35]2)[CH2:34][CH2:33]1.[NH2:21][CH2:22][CH:23]([OH:24])[c:25]1[cH:26][cH:27][c:28]([OH:29])[cH:30][c:31]1[OH:32] | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([S:9](=[O:10])(=[O:11])[NH:12][c:13]2[cH:14][cH:15][c:16]([N:17]3[CH2:18][CH2:19][CH:20]([NH:21][CH2:22][CH:23]([OH:24])[c:25]4[cH:26][cH:27][c:28]([OH:29])[cH:30][c:31]4[OH:32])[CH2:33][CH2:34]3)[cH:35][cH:36]2)[cH:37][cH:38]1 | ([C:2]-[CH;D3;+0:1](-[C:3])-[NH;D2;+0:5]-[C:4])>>(O=[C;H0;D3;+0:1](-[C:2])-[C:3]).([C:4]-[NH2;D1;+0:5]) | 67be25fd3ed7bf7f205940372151b70bd780167c6e07893adbc37ca7 | 1 | 1 | null | 236 |
164,820 | 580,377 | 965,710 | [CH:1]1([NH:7][C:8](=[O:26])[C:9]([S:12][C:13]2[CH:25]=[CH:24][C:16]([O:17][CH2:18][C:19]([O:21]CC)=[O:20])=[CH:15][CH:14]=2)([CH3:11])[CH3:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Li+].[OH-].O>C1COCC1.CO>[CH:1]1([NH:7][C:8](=[O:26])[C:9]([S:12][C:13]2[CH:14]=[CH:15][C:16]([O:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:24][CH:25]=2)([CH3:11])[CH3:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1 | |f:1.2.3,4.5| | US07687665B2_0697 | 2,010 | C1CCOC1.CC[O:13][C:11]([CH2:10][O:9][c:8]1[cH:7][cH:6][c:5]([S:4][C:2]([CH3:1])([CH3:3])[C:16](=[O:17])[NH:18][CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]2)[cH:15][cH:14]1)=[O:12].CO.O.[Li+].[OH-]>>[CH3:1][C:2]([CH3:3])([S:4][c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][C:11](=[O:12])[OH:13])[cH:14][cH:15]1)[C:16](=[O:17])[NH:18][CH:19]1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1 | 0.433688 | C1CCOC1~CO.CCOC(=O)COc1ccc(SC(C)(C)C(=O)NC2CCCCC2)cc1.O~[Li+]~[OH-]>>CC(C)(Sc1ccc(OCC(=O)O)cc1)C(=O)NC1CCCCC1 | C1CCOC1.CCOC(=O)COc1ccc(SC(C)(C)C(=O)NC2CCCCC2)cc1.CO.O.[Li+].[OH-]>>CC(C)(Sc1ccc(OCC(=O)O)cc1)C(=O)NC1CCCCC1 | US07687665B2_0697grants | 0f05997fd2d7425e1d3204d732de808d85b590109d743647ae7a3e27 | C1CCOC1.CC[O:13][C:11]([CH2:10][O:9][c:8]1[cH:7][cH:6][c:5]([S:4][C:2]([CH3:1])([CH3:3])[C:16](=[O:17])[NH:18][CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]2)[cH:15][cH:14]1)=[O:12].CO.O.[Li+].[OH-] | [CH3:1][C:2]([CH3:3])([S:4][c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][C:11](=[O:12])[OH:13])[cH:14][cH:15]1)[C:16](=[O:17])[NH:18][CH:19]1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1 | ([C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1])>>(C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]) | 9a4c5ceadb3b4a753bb8f03491f138cd875a84f1d327e818237f90df | 1 | 1 | C1CCOC1.CO.O.[Li+].[OH-] | 7 |
120,167 | 446,080 | 757,959 | O1[C:5]2([CH2:10][CH2:9][N:8]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[CH2:21][C@H:20]([CH2:22][N:23]5[CH:27]=[CH:26][N:25]=[N:24]5)[O:19][C:18]4=[O:28])=[CH:13][C:12]=3[F:29])[CH2:7][CH2:6]2)[O:4]CC1>C(O)(=O)C.O>[O:4]=[C:5]1[CH2:6][CH2:7][N:8]([C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:21][C@H:20]([CH2:22][N:23]4[CH:27]=[CH:26][N:25]=[N:24]4)[O:19][C:18]3=[O:28])=[CH:13][C:12]=2[F:29])[CH2:9][CH2:10]1 | null | US07141583B2_0216 | 2,006 | C1C[O:1][C:2]2(O1)[CH2:3][CH2:4][N:5]([c:6]1[cH:7][cH:8][c:9]([N:10]3[CH2:11][C@H:12]([CH2:13][n:14]4[cH:15][cH:16][n:17][n:18]4)[O:19][C:20]3=[O:21])[cH:22][c:23]1[F:24])[CH2:25][CH2:26]2.CC(=O)O.O>>[O:1]=[C:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]([N:10]3[CH2:11][C@H:12]([CH2:13][n:14]4[cH:15][cH:16][n:17][n:18]4)[O:19][C:20]3=[O:21])[cH:22][c:23]2[F:24])[CH2:25][CH2:26]1 | 0.511718 | CC(=O)O.O.O=C1O[C@@H](Cn2ccnn2)CN1c1ccc(N2CCC3(CC2)OCCO3)c(F)c1>>O=C1CCN(c2ccc(N3C[C@H](Cn4ccnn4)OC3=O)cc2F)CC1 | CC(=O)O.O.O=C1O[C@@H](Cn2ccnn2)CN1c1ccc(N2CCC3(CC2)OCCO3)c(F)c1>>O=C1CCN(c2ccc(N3C[C@H](Cn4ccnn4)OC3=O)cc2F)CC1 | US07141583B2_0216grants | 2376a0772d468b3b7ee09aca03086d4c652302796dd2de252077cf72 | C1C[O:1][C:2]2(O1)[CH2:3][CH2:4][N:5]([c:6]1[cH:7][cH:8][c:9]([N:10]3[CH2:11][C@H:12]([CH2:13][n:14]4[cH:15][cH:16][n:17][n:18]4)[O:19][C:20]3=[O:21])[cH:22][c:23]1[F:24])[CH2:25][CH2:26]2.CC(=O)O.O | [O:1]=[C:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]([N:10]3[CH2:11][C@H:12]([CH2:13][n:14]4[cH:15][cH:16][n:17][n:18]4)[O:19][C:20]3=[O:21])[cH:22][c:23]2[F:24])[CH2:25][CH2:26]1 | ([C:1]-[C;H0;D3;+0:2](-[C:3])=[O;H0;D1;+0:4])>>([C:1]-[C;H0;D4;+0:2]1(-[C:3])-O-C-C-[O;H0;D2;+0:4]-1) | e7506b5dcebc1e1132cd14011cf5d80a1a3bec302d3ec77f83c62062 | 1 | 1 | CC(=O)O.O | 251 |
170,272 | 597,091 | 989,609 | [C:1](Cl)(=[O:4])[CH2:2][CH3:3].[CH2:6]([CH:9]1[CH2:14][CH2:13][CH:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:21]2[CH:22]=[C:23]([OH:27])[CH:24]=[CH:25][CH:26]=2)[CH2:11][CH2:10]1)[CH2:7][CH3:8].O.Cl>N1C=CC=CC=1>[C:1]([O:27][C:23]1[CH:24]=[CH:25][CH:26]=[C:21]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[CH:12]2[CH2:13][CH2:14][CH:9]([CH2:6][CH2:7][CH3:8])[CH2:10][CH2:11]2)[CH:22]=1)(=[O:4])[CH2:2][CH3:3] | null | US07740769B2_0169 | 2,010 | Cl.Cl[C:20](=[O:21])[CH2:22][CH3:23].O.[CH3:1][CH2:2][CH2:3][CH:4]1[CH2:5][CH2:6][CH:7]([c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2-[c:14]2[cH:15][cH:16][cH:17][c:18]([OH:19])[cH:24]2)[CH2:25][CH2:26]1.c1ccncc1>>[CH3:1][CH2:2][CH2:3][CH:4]1[CH2:5][CH2:6][CH:7]([c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2-[c:14]2[cH:15][cH:16][cH:17][c:18]([O:19][C:20](=[O:21])[CH2:22][CH3:23])[cH:24]2)[CH2:25][CH2:26]1 | 0.929995 | CCC(=O)Cl.CCCC1CCC(c2ccccc2-c2cccc(O)c2)CC1.Cl.O.c1ccncc1>>CCCC1CCC(c2ccccc2-c2cccc(OC(=O)CC)c2)CC1 | CCC(=O)Cl.CCCC1CCC(c2ccccc2-c2cccc(O)c2)CC1.Cl.O.c1ccncc1>>CCCC1CCC(c2ccccc2-c2cccc(OC(=O)CC)c2)CC1 | US07740769B2_0169grants | c66a7f048350729b246396a6419579afbe32efdcf6a2a72a86336549 | Cl.Cl[C:20](=[O:21])[CH2:22][CH3:23].O.[CH3:1][CH2:2][CH2:3][CH:4]1[CH2:5][CH2:6][CH:7]([c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2-[c:14]2[cH:15][cH:16][cH:17][c:18]([OH:19])[cH:24]2)[CH2:25][CH2:26]1.c1ccncc1 | [CH3:1][CH2:2][CH2:3][CH:4]1[CH2:5][CH2:6][CH:7]([c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2-[c:14]2[cH:15][cH:16][cH:17][c:18]([O:19][C:20](=[O:21])[CH2:22][CH3:23])[cH:24]2)[CH2:25][CH2:26]1 | ([C:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[O;H0;D2;+0:4]-[c:5])>>(Cl-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([OH;D1;+0:4]-[c:5]) | 6a3b76348d27d2fac81da4191667c52babbec7848f8fea7e2739ff3e | 1 | 1 | Cl.O.c1ccncc1 | 111 |
126,979 | 466,842 | 790,875 | C[O:2][C:3](=[O:34])[CH:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]#[C:13][C:14]2[CH:23]=[C:22]([CH:24]3[CH2:26][CH2:25]3)[C:21]3[CH:20]([N:27]([CH:29]4[CH2:31][CH2:30]4)[CH3:28])[CH2:19][CH2:18][C:17]([CH3:33])([CH3:32])[C:16]=3[CH:15]=2)=[CH:8][CH:7]=1)[CH3:5].[OH-].[Li+].[Cl-].[NH4+]>CO.O1CCCC1>[CH:24]1([C:22]2[C:21]3[CH:20]([N:27]([CH:29]4[CH2:30][CH2:31]4)[CH3:28])[CH2:19][CH2:18][C:17]([CH3:32])([CH3:33])[C:16]=3[CH:15]=[C:14]([C:13]#[C:12][C:9]3[CH:8]=[CH:7][C:6]([CH:4]([CH3:5])[C:3]([OH:34])=[O:2])=[CH:11][CH:10]=3)[CH:23]=2)[CH2:26][CH2:25]1 | |f:1.2,3.4| | US07226951B2_0823 | 2,007 | C1CCOC1.CO.C[O:5][C:3]([CH:2]([CH3:1])[c:6]1[cH:7][cH:8][c:9]([C:10]#[C:11][c:12]2[cH:13][c:14]([CH:15]3[CH2:16][CH2:17]3)[c:18]3[c:19]([cH:20]2)[C:21]([CH3:22])([CH3:23])[CH2:24][CH2:25][CH:26]3[N:27]([CH3:28])[CH:29]2[CH2:30][CH2:31]2)[cH:32][cH:33]1)=[O:4].[Cl-].[Li+].[NH4+].[OH-]>>[CH3:1][CH:2]([C:3](=[O:4])[OH:5])[c:6]1[cH:7][cH:8][c:9]([C:10]#[C:11][c:12]2[cH:13][c:14]([CH:15]3[CH2:16][CH2:17]3)[c:18]3[c:19]([cH:20]2)[C:21]([CH3:22])([CH3:23])[CH2:24][CH2:25][CH:26]3[N:27]([CH3:28])[CH:29]2[CH2:30][CH2:31]2)[cH:32][cH:33]1 | 0.654229 | C1CCOC1.CO.COC(=O)C(C)c1ccc(C#Cc2cc(C3CC3)c3c(c2)C(C)(C)CCC3N(C)C2CC2)cc1.[Cl-]~[NH4+].[Li+]~[OH-]>>CC(C(=O)O)c1ccc(C#Cc2cc(C3CC3)c3c(c2)C(C)(C)CCC3N(C)C2CC2)cc1 | C1CCOC1.CO.COC(=O)C(C)c1ccc(C#Cc2cc(C3CC3)c3c(c2)C(C)(C)CCC3N(C)C2CC2)cc1.[Cl-].[Li+].[NH4+].[OH-]>>CC(C(=O)O)c1ccc(C#Cc2cc(C3CC3)c3c(c2)C(C)(C)CCC3N(C)C2CC2)cc1 | US07226951B2_0823grants | 10269e0aaf0341f8e6a097db37fac1606c688cc3949b54879fbc8021 | C1CCOC1.CO.C[O:5][C:3]([CH:2]([CH3:1])[c:6]1[cH:7][cH:8][c:9]([C:10]#[C:11][c:12]2[cH:13][c:14]([CH:15]3[CH2:16][CH2:17]3)[c:18]3[c:19]([cH:20]2)[C:21]([CH3:22])([CH3:23])[CH2:24][CH2:25][CH:26]3[N:27]([CH3:28])[CH:29]2[CH2:30][CH2:31]2)[cH:32][cH:33]1)=[O:4].[Cl-].[Li+].[NH4+].[OH-] | [CH3:1][CH:2]([C:3](=[O:4])[OH:5])[c:6]1[cH:7][cH:8][c:9]([C:10]#[C:11][c:12]2[cH:13][c:14]([CH:15]3[CH2:16][CH2:17]3)[c:18]3[c:19]([cH:20]2)[C:21]([CH3:22])([CH3:23])[CH2:24][CH2:25][CH:26]3[N:27]([CH3:28])[CH:29]2[CH2:30][CH2:31]2)[cH:32][cH:33]1 | ([C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1])>>(C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]) | 0a02d2d47df007d05d29f7b852c5bfe9dcbd7a32224d027cc636bd27 | 1 | 1 | C1CCOC1.CO.[Cl-].[Li+].[NH4+].[OH-] | 88 |
394,877 | 1,252,205 | null | [CH2:1]([C@@H:5]1[NH:10][CH2:9][C@H:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[NH:7][C:6]1=[O:17])[CH:2]([CH3:4])[CH3:3].[Br:18][C:19]1[CH:24]=[CH:23][C:22]([C@@H:25]2[CH2:27][C@H:26]2[C:28](O)=[O:29])=[CH:21][CH:20]=1.C([C@@H]1N(C([C@@H]2C[C@H]2C2C=CC=CC=2)=O)C[C@H](CC(C)C)NC1=O)C(C)C>>[Br:18][C:19]1[CH:20]=[CH:21][C:22]([C@@H:25]2[CH2:27][C@H:26]2[C:28]([N:10]2[CH2:9][C@H:8]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:7][C:6](=[O:17])[C@@H:5]2[CH2:1][CH:2]([CH3:4])[CH3:3])=[O:29])=[CH:23][CH:24]=1 | null | US20120202794A1_2512 | 2,012 | CC(C)C[C@H]1CN(C(=O)[C@@H]2C[C@H]2c2ccccc2)[C@@H](CC(C)C)C(=O)N1.O[C:18](=[O:19])[C@@H:20]1[CH2:21][C@H:22]1[c:23]1[cH:24][cH:25][c:26]([Br:27])[cH:28][cH:29]1.[CH3:1][CH:2]([CH3:3])[CH2:4][C@H:5]1[C:6](=[O:7])[NH:8][C@@H:9]([c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[CH2:16][NH:17]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][C@H:5]1[C:6](=[O:7])[NH:8][C@@H:9]([c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[CH2:16][N:17]1[C:18](=[O:19])[C@@H:20]1[CH2:21][C@H:22]1[c:23]1[cH:24][cH:25][c:26]([Br:27])[cH:28][cH:29]1 | 0.437393 | CC(C)C[C@@H]1NC[C@H](c2ccccc2)NC1=O.CC(C)C[C@H]1CN(C(=O)[C@@H]2C[C@H]2c2ccccc2)[C@@H](CC(C)C)C(=O)N1.O=C(O)[C@@H]1C[C@H]1c1ccc(Br)cc1>>CC(C)C[C@H]1C(=O)N[C@@H](c2ccccc2)CN1C(=O)[C@@H]1C[C@H]1c1ccc(Br)cc1 | CC(C)C[C@@H]1NC[C@H](c2ccccc2)NC1=O.CC(C)C[C@H]1CN(C(=O)[C@@H]2C[C@H]2c2ccccc2)[C@@H](CC(C)C)C(=O)N1.O=C(O)[C@@H]1C[C@H]1c1ccc(Br)cc1>>CC(C)C[C@H]1C(=O)N[C@@H](c2ccccc2)CN1C(=O)[C@@H]1C[C@H]1c1ccc(Br)cc1 | US20120202794A1_2512apps | 11d52349eb15edb357366a8647da3f4802faefe1159f515ea00f7b56 | CC(C)C[C@H]1CN(C(=O)[C@@H]2C[C@H]2c2ccccc2)[C@@H](CC(C)C)C(=O)N1.O[C:18](=[O:19])[C@@H:20]1[CH2:21][C@H:22]1[c:23]1[cH:24][cH:25][c:26]([Br:27])[cH:28][cH:29]1.[CH3:1][CH:2]([CH3:3])[CH2:4][C@H:5]1[C:6](=[O:7])[NH:8][C@@H:9]([c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[CH2:16][NH:17]1 | [CH3:1][CH:2]([CH3:3])[CH2:4][C@H:5]1[C:6](=[O:7])[NH:8][C@@H:9]([c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[CH2:16][N:17]1[C:18](=[O:19])[C@@H:20]1[CH2:21][C@H:22]1[c:23]1[cH:24][cH:25][c:26]([Br:27])[cH:28][cH:29]1 | ([#7:4]-[C:5](=[O;D1;H0:6])-[C:7]-[N;H0;D3;+0:8](-[C:9])-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3])>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([#7:4]-[C:5](=[O;D1;H0:6])-[C:7]-[NH;D2;+0:8]-[C:9]) | a26f6aecea692dab5140254167a4cba21c6ee8b406a4bac29afe51de | 1 | 1 | CC(C)C[C@H]1CN(C(=O)[C@@H]2C[C@H]2c2ccccc2)[C@@H](CC(C)C)C(=O)N1 | 297 |
103,492 | 396,012 | 677,077 | [C:1]([O:4][CH:5]([CH2:9][CH:10]=[C:11]([CH3:19])[CH2:12][CH2:13][CH2:14][CH:15]([CH3:18])[CH2:16][OH:17])[C:6](=[O:8])[CH3:7])(=[O:3])[CH3:2].[O:20]1[CH:25]=[CH:24][CH2:23][CH2:22][CH2:21]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C(OCC)C>C(Cl)Cl>[C:1]([O:4][CH:5]([CH2:9][CH:10]=[C:11]([CH3:19])[CH2:12][CH2:13][CH2:14][CH:15]([CH3:18])[CH2:16][O:17][CH:21]1[CH2:22][CH2:23][CH2:24][CH2:25][O:20]1)[C:6](=[O:8])[CH3:7])(=[O:3])[CH3:2] | |f:2.3| | US06867333B2_00519 | 2,005 | CCOCC.Cc1ccc(S(=O)(=O)[O-])cc1.ClCCl.[CH3:1][C:2](=[O:3])[O:4][CH:5]([CH2:6][CH:7]=[C:8]([CH3:9])[CH2:10][CH2:11][CH2:12][CH:13]([CH3:14])[CH2:15][OH:16])[C:23]([CH3:24])=[O:25].[CH:17]1=[CH:18][CH2:19][CH2:20][CH2:21][O:22]1.c1cc[nH+]cc1>>[CH3:1][C:2](=[O:3])[O:4][CH:5]([CH2:6][CH:7]=[C:8]([CH3:9])[CH2:10][CH2:11][CH2:12][CH:13]([CH3:14])[CH2:15][O:16][CH:17]1[CH2:18][CH2:19][CH2:20][CH2:21][O:22]1)[C:23]([CH3:24])=[O:25] | 0.864439 | C1=COCCC1.CC(=O)OC(CC=C(C)CCCC(C)CO)C(C)=O.CCOCC.Cc1ccc(S(=O)(=O)[O-])cc1~c1cc[nH+]cc1.ClCCl>>CC(=O)OC(CC=C(C)CCCC(C)COC1CCCCO1)C(C)=O | C1=COCCC1.CC(=O)OC(CC=C(C)CCCC(C)CO)C(C)=O.CCOCC.Cc1ccc(S(=O)(=O)[O-])cc1.ClCCl.c1cc[nH+]cc1>>CC(=O)OC(CC=C(C)CCCC(C)COC1CCCCO1)C(C)=O | US06867333B2_00519grants | 93cd9d834fd63253d0639a32f3fbe345a4501f4df71f6af3c5e1663b | CCOCC.Cc1ccc(S(=O)(=O)[O-])cc1.ClCCl.[CH3:1][C:2](=[O:3])[O:4][CH:5]([CH2:6][CH:7]=[C:8]([CH3:9])[CH2:10][CH2:11][CH2:12][CH:13]([CH3:14])[CH2:15][OH:16])[C:23]([CH3:24])=[O:25].[CH:17]1=[CH:18][CH2:19][CH2:20][CH2:21][O:22]1.c1cc[nH+]cc1 | [CH3:1][C:2](=[O:3])[O:4][CH:5]([CH2:6][CH:7]=[C:8]([CH3:9])[CH2:10][CH2:11][CH2:12][CH:13]([CH3:14])[CH2:15][O:16][CH:17]1[CH2:18][CH2:19][CH2:20][CH2:21][O:22]1)[C:23]([CH3:24])=[O:25] | ([#8:1]-[CH;D3;+0:2](-[CH2;D2;+0:3]-[C:4])-[O;H0;D2;+0:6]-[C:5])>>([#8:1]-[CH;D2;+0:2]=[CH;D2;+0:3]-[C:4]).([C:5]-[OH;D1;+0:6]) | 01eb7ebee28065e078188d8f5911d94043d0ed8be715dde0c587a4a2 | 0.5 | 2 | CCOCC.Cc1ccc(S(=O)(=O)[O-])cc1.ClCCl.c1cc[nH+]cc1 | 141 |
37,599 | 169,175 | 271,372 | [I:1][N:2]([C:7]([O:9][CH2:10][C:11]#[CH:12])=[O:8])[CH2:3][C:4]([OH:6])=[O:5].N12CCCN=C1CCCCC2.[CH2:24](Br)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]>C(#N)C>[CH2:24]([O:5][C:4](=[O:6])[CH2:3][N:2]([C:7]([O:9][CH2:10][C:11]#[CH:12])=[O:8])[I:1])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31] | null | US05209930_ | 1,993 | Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].C1CCC2=NCCCN2CC1.CC#N.[CH:1]#[C:2][CH2:3][O:4][C:5](=[O:6])[N:7]([I:8])[CH2:9][C:10](=[O:11])[OH:12]>>[CH:1]#[C:2][CH2:3][O:4][C:5](=[O:6])[N:7]([I:8])[CH2:9][C:10](=[O:11])[O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20] | 0.901517 | C#CCOC(=O)N(I)CC(=O)O.C1CCC2=NCCCN2CC1.CC#N.CCCCCCCCBr>>C#CCOC(=O)N(I)CC(=O)OCCCCCCCC | C#CCOC(=O)N(I)CC(=O)O.C1CCC2=NCCCN2CC1.CC#N.CCCCCCCCBr>>C#CCOC(=O)N(I)CC(=O)OCCCCCCCC | US05209930_grants | 3ff3186360544a20207ab9798f2e97220c3a91a040bb7a4e499a67af | Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].C1CCC2=NCCCN2CC1.CC#N.[CH:1]#[C:2][CH2:3][O:4][C:5](=[O:6])[N:7]([I:8])[CH2:9][C:10](=[O:11])[OH:12] | [CH:1]#[C:2][CH2:3][O:4][C:5](=[O:6])[N:7]([I:8])[CH2:9][C:10](=[O:11])[O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20] | ([C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[C:4]=[O;D1;H0:3])>>(Br-[CH2;D2;+0:1]-[C:2]).([O;D1;H0:3]=[C:4]-[OH;D1;+0:5]) | 14822db80ce8fc6571cf8af82ebb2ec86be120740cdeca6edd3bdc98 | 0.5 | 2 | C1CCC2=NCCCN2CC1.CC#N | 416 |
141,223 | 509,557 | 854,828 | C(=O)([O-])[O-].[K+].[K+].[CH2:7]([NH:9][CH2:10][CH3:11])[CH3:8].[Cl:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH3:24])[CH:21]=2)[C:16]([C:25]2[CH:30]=[CH:29][C:28]([CH2:31]Cl)=[CH:27][CH:26]=2)=[N:15][N:14]=1>C(O)C>[Cl:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH3:24])[CH:21]=2)[C:16]([C:25]2[CH:30]=[CH:29][C:28]([CH2:31][N:9]([CH2:10][CH3:11])[CH2:7][CH3:8])=[CH:27][CH:26]=2)=[N:15][N:14]=1 | |f:0.1.2| | US07423030B2_0467 | 2,008 | CCO.Cl[CH2:6][c:7]1[cH:8][cH:9][c:10](-[c:11]2[n:12][n:13][c:14]([Cl:15])[c:16]3[cH:17][c:18]([O:19][CH3:20])[cH:21][cH:22][c:23]23)[cH:24][cH:25]1.O=C([O-])[O-].[CH3:1][CH2:2][NH:3][CH2:4][CH3:5].[K+].[K+]>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][c:7]1[cH:8][cH:9][c:10](-[c:11]2[n:12][n:13][c:14]([Cl:15])[c:16]3[cH:17][c:18]([O:19][CH3:20])[cH:21][cH:22][c:23]23)[cH:24][cH:25]1 | 0.821218 | CCNCC.CCO.COc1ccc2c(-c3ccc(CCl)cc3)nnc(Cl)c2c1.O=C([O-])[O-]~[K+]~[K+]>>CCN(CC)Cc1ccc(-c2nnc(Cl)c3cc(OC)ccc23)cc1 | CCNCC.CCO.COc1ccc2c(-c3ccc(CCl)cc3)nnc(Cl)c2c1.O=C([O-])[O-].[K+].[K+]>>CCN(CC)Cc1ccc(-c2nnc(Cl)c3cc(OC)ccc23)cc1 | US07423030B2_0467grants | f2886f489b8d74ff0d11fd64798683df9d6c70169de2958d4893c716 | CCO.Cl[CH2:6][c:7]1[cH:8][cH:9][c:10](-[c:11]2[n:12][n:13][c:14]([Cl:15])[c:16]3[cH:17][c:18]([O:19][CH3:20])[cH:21][cH:22][c:23]23)[cH:24][cH:25]1.O=C([O-])[O-].[CH3:1][CH2:2][NH:3][CH2:4][CH3:5].[K+].[K+] | [CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][c:7]1[cH:8][cH:9][c:10](-[c:11]2[n:12][n:13][c:14]([Cl:15])[c:16]3[cH:17][c:18]([O:19][CH3:20])[cH:21][cH:22][c:23]23)[cH:24][cH:25]1 | ([C:3]-[N;H0;D3;+0:4](-[C:5])-[CH2;D2;+0:1]-[c:2])>>(Cl-[CH2;D2;+0:1]-[c:2]).([C:3]-[NH;D2;+0:4]-[C:5]) | 6f8a7db848a9ef8856658f22091cd0a39a7c1e40ccd5dceed9896a48 | 1 | 1 | CCO.O=C([O-])[O-].[K+].[K+] | 156 |
272,132 | 892,927 | 1,488,937 | Cl[C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[C:9]2[C:5]([C:6](=[O:15])[C:7](=[O:14])[NH:8]2)=[CH:4][CH:3]=1.[CH3:16][O-:17].[Na+].Cl>CO>[CH3:16][O:17][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[C:9]2[C:5]([C:6](=[O:15])[C:7](=[O:14])[NH:8]2)=[CH:4][CH:3]=1 | |f:1.2| | US08785460B2_1517 | 2,014 | C[O-].Cl.Cl[c:3]1[cH:4][cH:5][c:6]2[c:7]([c:8]1[N+:9](=[O:10])[O-:11])[NH:12][C:13](=[O:14])[C:15]2=[O:16].[CH3:1][OH:2].[Na+]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([c:8]1[N+:9](=[O:10])[O-:11])[NH:12][C:13](=[O:14])[C:15]2=[O:16] | 0.623277 | CO.C[O-]~[Na+].Cl.O=C1Nc2c(ccc(Cl)c2[N+](=O)[O-])C1=O>>COc1ccc2c(c1[N+](=O)[O-])NC(=O)C2=O | CO.C[O-].Cl.O=C1Nc2c(ccc(Cl)c2[N+](=O)[O-])C1=O.[Na+]>>COc1ccc2c(c1[N+](=O)[O-])NC(=O)C2=O | US08785460B2_1517grants | 56738a91f9ad02e0e954c7a46650db248f1bb91ec6197cf281076aa9 | C[O-].Cl.Cl[c:3]1[cH:4][cH:5][c:6]2[c:7]([c:8]1[N+:9](=[O:10])[O-:11])[NH:12][C:13](=[O:14])[C:15]2=[O:16].[CH3:1][OH:2].[Na+] | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([c:8]1[N+:9](=[O:10])[O-:11])[NH:12][C:13](=[O:14])[C:15]2=[O:16] | ([C;D1;H3:4]-[O;H0;D2;+0:5]-[c;H0;D3;+0:1](:[c:2]):[c:3])>>(Cl-[c;H0;D3;+0:1](:[c:2]):[c:3]).([C;D1;H3:4]-[OH;D1;+0:5]) | dc1df440495b5178d2068b6ce10847de092b0023c735e4417e8ef4f7 | 1 | 1 | C[O-].Cl.[Na+] | 57 |
195,519 | 670,125 | 1,107,773 | [CH2:1]([N:3]([CH2:19][CH3:20])[CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][C:9]2[NH:12][C:13]([CH:16]=O)=[C:14]([CH3:15])[C:8]=2[C:7]1=[O:18])[CH3:2].[F:21][C:22]1[CH:23]=[C:24]2[C:28](=[C:29]([Br:31])[CH:30]=1)[NH:27][C:26](=[O:32])[CH2:25]2>>[Br:31][C:29]1[CH:30]=[C:22]([F:21])[CH:23]=[C:24]2[C:28]=1[NH:27][C:26](=[O:32])[C:25]2=[CH:16][C:13]1[NH:12][C:9]2[CH2:10][CH2:11][N:6]([CH2:5][CH2:4][N:3]([CH2:19][CH3:20])[CH2:1][CH3:2])[C:7](=[O:18])[C:8]=2[C:14]=1[CH3:15] | null | US08012966B2_0397 | 2,011 | O=[CH:14][c:13]1[nH:12][c:11]2[c:29]([c:27]1[CH3:28])[C:30](=[O:31])[N:8]([CH2:7][CH2:6][N:3]([CH2:2][CH3:1])[CH2:4][CH3:5])[CH2:9][CH2:10]2.[CH2:15]1[C:16](=[O:17])[NH:18][c:19]2[c:20]([Br:21])[cH:22][c:23]([F:24])[cH:25][c:26]21>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][N:8]1[CH2:9][CH2:10][c:11]2[nH:12][c:13]([CH:14]=[C:15]3[C:16](=[O:17])[NH:18][c:19]4[c:20]([Br:21])[cH:22][c:23]([F:24])[cH:25][c:26]43)[c:27]([CH3:28])[c:29]2[C:30]1=[O:31] | 0.878445 | CCN(CC)CCN1CCc2[nH]c(C=O)c(C)c2C1=O.O=C1Cc2cc(F)cc(Br)c2N1>>CCN(CC)CCN1CCc2[nH]c(C=C3C(=O)Nc4c(Br)cc(F)cc43)c(C)c2C1=O | CCN(CC)CCN1CCc2[nH]c(C=O)c(C)c2C1=O.O=C1Cc2cc(F)cc(Br)c2N1>>CCN(CC)CCN1CCc2[nH]c(C=C3C(=O)Nc4c(Br)cc(F)cc43)c(C)c2C1=O | US08012966B2_0397grants | b3559543cc3f8bbdce22143cb1d651cb1a2c20d6f45525b79f3c9ca7 | O=[CH:14][c:13]1[nH:12][c:11]2[c:29]([c:27]1[CH3:28])[C:30](=[O:31])[N:8]([CH2:7][CH2:6][N:3]([CH2:2][CH3:1])[CH2:4][CH3:5])[CH2:9][CH2:10]2.[CH2:15]1[C:16](=[O:17])[NH:18][c:19]2[c:20]([Br:21])[cH:22][c:23]([F:24])[cH:25][c:26]21 | [CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][N:8]1[CH2:9][CH2:10][c:11]2[nH:12][c:13]([CH:14]=[C:15]3[C:16](=[O:17])[NH:18][c:19]4[c:20]([Br:21])[cH:22][c:23]([F:24])[cH:25][c:26]43)[c:27]([CH3:28])[c:29]2[C:30]1=[O:31] | ([#7:4]-[C:5](=[O;D1;H0:6])-[C;H0;D3;+0:7](-[c:8])=[CH;D2;+0:1]-[c:2]:[#7;a:3])>>(O=[CH;D2;+0:1]-[c:2]:[#7;a:3]).([#7:4]-[C:5](=[O;D1;H0:6])-[CH2;D2;+0:7]-[c:8]) | 7924cbf0da79d1713912e854ce0d084a37ce4e2f134b0ab1fff2a499 | 1 | 1 | null | 440 |
141,229 | 509,572 | 854,843 | [CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:8][NH:9][C:10]2=O)=[CH:5][CH:4]=1.P(Cl)(Cl)([Cl:24])=O>>[Cl:24][C:10]1[C:11]2[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=2)[C:7]([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:8][N:9]=1 | null | US07423030B2_0520 | 2,008 | O=P(Cl)(Cl)[Cl:19].O=[c:18]1[nH:17][n:16][c:7]([CH2:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:21][c:20]21>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([CH2:8][CH2:9][c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[n:16][n:17][c:18]([Cl:19])[c:20]2[cH:21]1 | 0.339137 | COc1ccc2c(CCc3ccccc3)n[nH]c(=O)c2c1.O=P(Cl)(Cl)Cl>>COc1ccc2c(CCc3ccccc3)nnc(Cl)c2c1 | COc1ccc2c(CCc3ccccc3)n[nH]c(=O)c2c1.O=P(Cl)(Cl)Cl>>COc1ccc2c(CCc3ccccc3)nnc(Cl)c2c1 | US07423030B2_0520grants | c092047804dc233ff120bd73355261e36e8b1fcbdbc0c81114aa333e | O=P(Cl)(Cl)[Cl:19].O=[c:18]1[nH:17][n:16][c:7]([CH2:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:21][c:20]21 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([CH2:8][CH2:9][c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[n:16][n:17][c:18]([Cl:19])[c:20]2[cH:21]1 | ([#7;a:5]:[n;H0;D2;+0:4]:[c;H0;D3;+0:2](-[Cl;H0;D1;+0:1]):[c:3])>>(Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1]).(O=[c;H0;D3;+0:2](:[c:3]):[nH;D2;+0:4]:[#7;a:5]) | 6ca9b283fabd775321a59902016a6d06312ee29eda5dd1df1aa040ad | 1 | 1 | null | 537 |
249,421 | 827,765 | 1,372,500 | [Cl:1][C:2]1[CH:3]=[C:4]([C:10]2([C:27]([F:30])([F:29])[F:28])[O:14][N:13]=[C:12]([C:15]3[N:16]4[C:20]([C:21]([C:24]([OH:26])=O)=[CH:22][CH:23]=3)=[CH:19][CH:18]=[CH:17]4)[CH2:11]2)[CH:5]=[C:6]([Cl:9])[C:7]=1[Cl:8].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC.Cl.[NH2:63][CH2:64][C:65]1[CH:66]=[CH:67][C:68]2[C:72]([CH3:74])([CH3:73])[O:71][B:70]([OH:75])[C:69]=2[CH:76]=1>CN(C=O)C.CC(=O)OCC>[OH:75][B:70]1[C:69]2[CH:76]=[C:65]([CH2:64][NH:63][C:24]([C:21]3[C:20]4[N:16]([CH:17]=[CH:18][CH:19]=4)[C:15]([C:12]4[CH2:11][C:10]([C:4]5[CH:3]=[C:2]([Cl:1])[C:7]([Cl:8])=[C:6]([Cl:9])[CH:5]=5)([C:27]([F:30])([F:29])[F:28])[O:14][N:13]=4)=[CH:23][CH:22]=3)=[O:26])[CH:66]=[CH:67][C:68]=2[C:72]([CH3:74])([CH3:73])[O:71]1 | |f:1.2,4.5| | US08546357B2_0609 | 2,013 | CCN(CC)CC.CCOC(C)=O.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.Cl.F[P-](F)(F)(F)(F)F.O[C:12](=[O:13])[c:14]1[cH:15][cH:16][c:17]([C:18]2=[N:19][O:20][C:21]([c:22]3[cH:23][c:24]([Cl:25])[c:26]([Cl:27])[c:28]([Cl:29])[cH:30]3)([C:31]([F:32])([F:33])[F:34])[CH2:35]2)[n:36]2[cH:37][cH:38][cH:39][c:40]12.[CH3:1][C:2]1([CH3:3])[O:4][B:5]([OH:6])[c:7]2[cH:8][c:9]([CH2:10][NH2:11])[cH:41][cH:42][c:43]21>>[CH3:1][C:2]1([CH3:3])[O:4][B:5]([OH:6])[c:7]2[cH:8][c:9]([CH2:10][NH:11][C:12](=[O:13])[c:14]3[cH:15][cH:16][c:17]([C:18]4=[N:19][O:20][C:21]([c:22]5[cH:23][c:24]([Cl:25])[c:26]([Cl:27])[c:28]([Cl:29])[cH:30]5)([C:31]([F:32])([F:33])[F:34])[CH2:35]4)[n:36]4[cH:37][cH:38][cH:39][c:40]34)[cH:41][cH:42][c:43]21 | 0.31526 | CC1(C)OB(O)c2cc(CN)ccc21~Cl.CCN(CC)CC.CCOC(C)=O.CN(C)C(On1nnc2cccnc21)=[N+](C)C~F[P-](F)(F)(F)(F)F.CN(C)C=O.O=C(O)c1ccc(C2=NOC(c3cc(Cl)c(Cl)c(Cl)c3)(C(F)(F)F)C2)n2cccc12>>CC1(C)OB(O)c2cc(CNC(=O)c3ccc(C4=NOC(c5cc(Cl)c(Cl)c(Cl)c5)(C(F)(F)F)C4)n4cccc34)ccc21 | CC1(C)OB(O)c2cc(CN)ccc21.CCN(CC)CC.CCOC(C)=O.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.Cl.F[P-](F)(F)(F)(F)F.O=C(O)c1ccc(C2=NOC(c3cc(Cl)c(Cl)c(Cl)c3)(C(F)(F)F)C2)n2cccc12>>CC1(C)OB(O)c2cc(CNC(=O)c3ccc(C4=NOC(c5cc(Cl)c(Cl)c(Cl)c5)(C(F)(F)F)C4)n4cccc34)ccc21 | US08546357B2_0609grants | 62a902659219463a5e56796b7736a04f704cab63edbea3c3f1d1ee02 | CCN(CC)CC.CCOC(C)=O.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.Cl.F[P-](F)(F)(F)(F)F.O[C:12](=[O:13])[c:14]1[cH:15][cH:16][c:17]([C:18]2=[N:19][O:20][C:21]([c:22]3[cH:23][c:24]([Cl:25])[c:26]([Cl:27])[c:28]([Cl:29])[cH:30]3)([C:31]([F:32])([F:33])[F:34])[CH2:35]2)[n:36]2[cH:37][cH:38][cH:39][c:40]12.[CH3:1][C:2]1([CH3:3])[O:4][B:5]([OH:6])[c:7]2[cH:8][c:9]([CH2:10][NH2:11])[cH:41][cH:42][c:43]21 | [CH3:1][C:2]1([CH3:3])[O:4][B:5]([OH:6])[c:7]2[cH:8][c:9]([CH2:10][NH:11][C:12](=[O:13])[c:14]3[cH:15][cH:16][c:17]([C:18]4=[N:19][O:20][C:21]([c:22]5[cH:23][c:24]([Cl:25])[c:26]([Cl:27])[c:28]([Cl:29])[cH:30]5)([C:31]([F:32])([F:33])[F:34])[CH2:35]4)[n:36]4[cH:37][cH:38][cH:39][c:40]34)[cH:41][cH:42][c:43]21 | ([#7;a:5]:[c:4]:[c:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[C:7]-[c:8]1:[c:9]:[c:10]:[c:11]:[c:12]:[c:13]:1)>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]:[c:4]:[#7;a:5]).([NH2;D1;+0:6]-[C:7]-[c:8]1:[c:9]:[c:10]:[c:11]:[c:12]:[c:13]:1) | be66a529f0d7df0d697f6999dd10c354849754090fadeb4dc93ab6e0 | 1 | 1 | CCN(CC)CC.CCOC(C)=O.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.Cl.F[P-](F)(F)(F)(F)F | 790 |
131,791 | 480,554 | 810,455 | C(OC([N:8]([CH:12]1[CH2:17][CH2:16][N:15]([CH2:18][C:19]2[CH:20]=[N:21][CH:22]=[CH:23][C:24]=2[O:25][CH3:26])[CH2:14][CH2:13]1)[CH:9]([CH3:11])[CH3:10])=O)(C)(C)C.Cl>O1CCOCC1>[CH:9]([NH:8][CH:12]1[CH2:13][CH2:14][N:15]([CH2:18][C:19]2[CH:20]=[N:21][CH:22]=[CH:23][C:24]=2[O:25][CH3:26])[CH2:16][CH2:17]1)([CH3:11])[CH3:10] | null | US07285564B2_0316 | 2,007 | C1COCCO1.CC(C)(C)OC(=O)[N:14]([CH:13]1[CH2:12][CH2:11][N:10]([CH2:9][c:8]2[c:3]([O:2][CH3:1])[cH:4][cH:5][n:6][cH:7]2)[CH2:19][CH2:18]1)[CH:15]([CH3:16])[CH3:17].Cl>>[CH3:1][O:2][c:3]1[cH:4][cH:5][n:6][cH:7][c:8]1[CH2:9][N:10]1[CH2:11][CH2:12][CH:13]([NH:14][CH:15]([CH3:16])[CH3:17])[CH2:18][CH2:19]1 | 0.800594 | C1COCCO1.COc1ccncc1CN1CCC(N(C(=O)OC(C)(C)C)C(C)C)CC1.Cl>>COc1ccncc1CN1CCC(NC(C)C)CC1 | C1COCCO1.COc1ccncc1CN1CCC(N(C(=O)OC(C)(C)C)C(C)C)CC1.Cl>>COc1ccncc1CN1CCC(NC(C)C)CC1 | US07285564B2_0316grants | e6bd35fe4549b8ac0113c74c49ecd3c8e829908cb01f93a9b0d3fb40 | C1COCCO1.CC(C)(C)OC(=O)[N:14]([CH:13]1[CH2:12][CH2:11][N:10]([CH2:9][c:8]2[c:3]([O:2][CH3:1])[cH:4][cH:5][n:6][cH:7]2)[CH2:19][CH2:18]1)[CH:15]([CH3:16])[CH3:17].Cl | [CH3:1][O:2][c:3]1[cH:4][cH:5][n:6][cH:7][c:8]1[CH2:9][N:10]1[CH2:11][CH2:12][CH:13]([NH:14][CH:15]([CH3:16])[CH3:17])[CH2:18][CH2:19]1 | ([C:2]-[NH;D2;+0:1]-[C:3])>>(C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2])-[C:3]) | 55396c1492cc3823f0701ef923544f9f4c1af584b69f4ce5650dc5ae | 1 | 1 | C1COCCO1.Cl | 575 |
311,605 | 1,012,938 | 1,714,464 | [C:1]([O:5][C:6]([NH:8][C@H:9]([C:15]([OH:17])=O)[CH2:10][O:11][C:12]#[C:13][CH3:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:19][O:20][C:21](=[O:24])[CH2:22][NH2:23].C(N(CC)C(C)C)(C)C.C1C=C2N=NN(O)C2=CC=1.O.CCN=C=NCCCN(C)C.Cl>CN(C=O)C>[CH3:19][O:20][C:21](=[O:24])[CH2:22][NH:23][C:15](=[O:17])[C@H:9]([CH2:10][O:11][C:12]#[C:13][CH3:14])[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7] | |f:1.2,4.5,6.7| | US09227995B2_0274 | 2,016 | CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.CN(C)C=O.Cl.Cl.O.O[C:15]([C@H:6]([CH2:5][O:4][C:3]#[C:2][CH3:1])[NH:7][C:8](=[O:9])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:16].On1nnc2ccccc21.[NH2:17][CH2:18][C:19](=[O:20])[O:21][CH3:22]>>[CH3:1][C:2]#[C:3][O:4][CH2:5][C@H:6]([NH:7][C:8](=[O:9])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])[C:15](=[O:16])[NH:17][CH2:18][C:19](=[O:20])[O:21][CH3:22] | 0.424929 | CC#COC[C@H](NC(=O)OC(C)(C)C)C(=O)O.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C~Cl.CN(C)C=O.COC(=O)CN~Cl.O~On1nnc2ccccc21>>CC#COC[C@H](NC(=O)OC(C)(C)C)C(=O)NCC(=O)OC | CC#COC[C@H](NC(=O)OC(C)(C)C)C(=O)O.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.CN(C)C=O.COC(=O)CN.Cl.Cl.O.On1nnc2ccccc21>>CC#COC[C@H](NC(=O)OC(C)(C)C)C(=O)NCC(=O)OC | US09227995B2_0274grants | 81f6bbbf7e1e6356d6ca9f52f9667dce62c027f78d0c1315055681e2 | CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.CN(C)C=O.Cl.Cl.O.O[C:15]([C@H:6]([CH2:5][O:4][C:3]#[C:2][CH3:1])[NH:7][C:8](=[O:9])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:16].On1nnc2ccccc21.[NH2:17][CH2:18][C:19](=[O:20])[O:21][CH3:22] | [CH3:1][C:2]#[C:3][O:4][CH2:5][C@H:6]([NH:7][C:8](=[O:9])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])[C:15](=[O:16])[NH:17][CH2:18][C:19](=[O:20])[O:21][CH3:22] | ([C:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:9]-[C:8]-[C:6](=[O;D1;H0:7])-[#8:5]-[C;D1;H3:4])>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([C;D1;H3:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]-[NH2;D1;+0:9]) | d902def43cc99d31140c9ddd32b2c934b92d7aa1b24f69887a6b7a98 | 1 | 1 | CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.CN(C)C=O.Cl.Cl.O.On1nnc2ccccc21 | 129 |
35,635 | 161,292 | 258,429 | [C:1]([C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5](O)=[O:6])#[N:2].S(Cl)([Cl:14])=O>>[C:1]([C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([Cl:14])=[O:6])#[N:2] | null | US05151435_ | 1,992 | O=S(Cl)[Cl:11].O[C:9]([c:8]1[c:3]([C:2]#[N:1])[cH:4][cH:5][cH:6][cH:7]1)=[O:10]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[C:9](=[O:10])[Cl:11] | 0.545303 | N#Cc1ccccc1C(=O)O.O=S(Cl)Cl>>N#Cc1ccccc1C(=O)Cl | N#Cc1ccccc1C(=O)O.O=S(Cl)Cl>>N#Cc1ccccc1C(=O)Cl | US05151435_grants | 4f05e6cc399869b525aea5181cf850663782475385718e40d8a34900 | O=S(Cl)[Cl:11].O[C:9]([c:8]1[c:3]([C:2]#[N:1])[cH:4][cH:5][cH:6][cH:7]1)=[O:10] | [N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[C:9](=[O:10])[Cl:11] | ([Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4])>>(Cl-S(=O)-[Cl;H0;D1;+0:1]).(O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4]) | b71280db4b70d661700213321895a7af48fe382569269c0e754a4f84 | 1 | 1 | null | 3 |
74,535 | 304,931 | 516,473 | [CH3:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH2:14][C@@H:15]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:16][OH:17]>>[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([NH:14][C@@H:15]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:16][OH:17])=[O:6] | null | US06251917B1_ | 2,001 | O[C:11]([c:10]1[c:2]([CH3:1])[cH:3][cH:4][c:5]([N+:6](=[O:7])[O-:8])[cH:9]1)=[O:12].[NH2:13][C@H:14]([CH2:15][OH:16])[CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([N+:6](=[O:7])[O-:8])[cH:9][c:10]1[C:11](=[O:12])[NH:13][C@H:14]([CH2:15][OH:16])[CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1 | 0.778759 | Cc1ccc([N+](=O)[O-])cc1C(=O)O.N[C@H](CO)Cc1ccccc1>>Cc1ccc([N+](=O)[O-])cc1C(=O)N[C@H](CO)Cc1ccccc1 | Cc1ccc([N+](=O)[O-])cc1C(=O)O.N[C@H](CO)Cc1ccccc1>>Cc1ccc([N+](=O)[O-])cc1C(=O)N[C@H](CO)Cc1ccccc1 | US06251917B1_grants | 45644730c29f7468e2a013b08db14daf1178854ec0785111248ed49e | O[C:11]([c:10]1[c:2]([CH3:1])[cH:3][cH:4][c:5]([N+:6](=[O:7])[O-:8])[cH:9]1)=[O:12].[NH2:13][C@H:14]([CH2:15][OH:16])[CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1 | [CH3:1][c:2]1[cH:3][cH:4][c:5]([N+:6](=[O:7])[O-:8])[cH:9][c:10]1[C:11](=[O:12])[NH:13][C@H:14]([CH2:15][OH:16])[CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1 | ([C:4]-[NH;D2;+0:5]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]).([C:4]-[NH2;D1;+0:5]) | 4b62c30a3b92b9941a5ddfdb3fbb597241af09409f8fb78aee5317d4 | 1 | 1 | null | 334 |
261,877 | 863,970 | 1,438,412 | [CH:1]1(/[CH:7]=[CH:8]/[C:9]2[CH:10]=[CH:11][C:12]([C:15]#[N:16])=[N:13][CH:14]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[NH2:16][CH2:15][C:12]1[CH:11]=[CH:10][C:9](/[CH:8]=[CH:7]/[CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:14][N:13]=1 | |f:1.2.3.4.5.6| | US08680091B2_0565 | 2,014 | C1CCOC1.[Al+3].[H-].[H-].[H-].[H-].[Li+].[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6](/[CH:7]=[CH:8]/[CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2)[cH:15][n:16]1>>[NH2:1][CH2:2][c:3]1[cH:4][cH:5][c:6](/[CH:7]=[CH:8]/[CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2)[cH:15][n:16]1 | 0.950274 | C1CCOC1.N#Cc1ccc(/C=C/C2CCCCC2)cn1.[Al+3]~[H-]~[H-]~[H-]~[H-]~[Li+]>>NCc1ccc(/C=C/C2CCCCC2)cn1 | C1CCOC1.N#Cc1ccc(/C=C/C2CCCCC2)cn1.[Al+3].[H-].[H-].[H-].[H-].[Li+]>>NCc1ccc(/C=C/C2CCCCC2)cn1 | US08680091B2_0565grants | 0e5069f4650efb5c4bf1d98bb72335b6061f27558cce77659160a877 | C1CCOC1.[Al+3].[H-].[H-].[H-].[H-].[Li+].[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6](/[CH:7]=[CH:8]/[CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2)[cH:15][n:16]1 | [NH2:1][CH2:2][c:3]1[cH:4][cH:5][c:6](/[CH:7]=[CH:8]/[CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2)[cH:15][n:16]1 | ([#7;a:1]:[c:2]-[CH2;D2;+0:3]-[NH2;D1;+0:4])>>([#7;a:1]:[c:2]-[C;H0;D2;+0:3]#[N;H0;D1;+0:4]) | 62f58ac1a980c03d4f52d6a68c87763429f1f9afe139e713b5eba6e6 | 1 | 1 | C1CCOC1.[Al+3].[H-].[H-].[H-].[H-].[Li+] | 205 |
284,987 | 931,174 | 1,560,190 | [CH3:1][O:2][C:3]([C:5]1[C:6]([OH:33])=[C:7]2[C:12](=[CH:13][N:14]=1)[N:11]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10](=[O:22])[C:9]([C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=1)=[CH:8]2)=[O:4].[Br:34]N1C(=O)CCC1=O>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[C:6]([OH:33])=[C:7]2[C:12](=[C:13]([Br:34])[N:14]=1)[N:11]([CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:10](=[O:22])[C:9]([C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=1)=[CH:8]2)=[O:4] | null | US08921389B2_0915 | 2,014 | ClCCl.O=C1CCC(=O)N1[Br:8].[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][cH:7][c:9]2[c:10]([cH:11][c:12](-[c:13]3[cH:14][cH:15][cH:16][c:17]([C:18]([F:19])([F:20])[F:21])[cH:22]3)[c:23](=[O:24])[n:25]2[CH2:26][c:27]2[cH:28][cH:29][cH:30][cH:31][cH:32]2)[c:33]1[OH:34]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][c:7]([Br:8])[c:9]2[c:10]([cH:11][c:12](-[c:13]3[cH:14][cH:15][cH:16][c:17]([C:18]([F:19])([F:20])[F:21])[cH:22]3)[c:23](=[O:24])[n:25]2[CH2:26][c:27]2[cH:28][cH:29][cH:30][cH:31][cH:32]2)[c:33]1[OH:34] | 0.314394 | COC(=O)c1ncc2c(cc(-c3cccc(C(F)(F)F)c3)c(=O)n2Cc2ccccc2)c1O.ClCCl.O=C1CCC(=O)N1Br>>COC(=O)c1nc(Br)c2c(cc(-c3cccc(C(F)(F)F)c3)c(=O)n2Cc2ccccc2)c1O | COC(=O)c1ncc2c(cc(-c3cccc(C(F)(F)F)c3)c(=O)n2Cc2ccccc2)c1O.ClCCl.O=C1CCC(=O)N1Br>>COC(=O)c1nc(Br)c2c(cc(-c3cccc(C(F)(F)F)c3)c(=O)n2Cc2ccccc2)c1O | US08921389B2_0915grants | 59a0f4c62d3fa2ef6ee98d9a83f5279d9a209fe744f7de7f459d23f4 | ClCCl.O=C1CCC(=O)N1[Br:8].[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][cH:7][c:9]2[c:10]([cH:11][c:12](-[c:13]3[cH:14][cH:15][cH:16][c:17]([C:18]([F:19])([F:20])[F:21])[cH:22]3)[c:23](=[O:24])[n:25]2[CH2:26][c:27]2[cH:28][cH:29][cH:30][cH:31][cH:32]2)[c:33]1[OH:34] | [CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][c:7]([Br:8])[c:9]2[c:10]([cH:11][c:12](-[c:13]3[cH:14][cH:15][cH:16][c:17]([C:18]([F:19])([F:20])[F:21])[cH:22]3)[c:23](=[O:24])[n:25]2[CH2:26][c:27]2[cH:28][cH:29][cH:30][cH:31][cH:32]2)[c:33]1[OH:34] | ([#7;a:2]:[c:3]:[c;H0;D3;+0:4](:[#7;a:5])-[Br;H0;D1;+0:1])>>(O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1]).([#7;a:2]:[c:3]:[cH;D2;+0:4]:[#7;a:5]) | 47082d3565332d60066063a580bfae7fb44013a2770c5adae63bf9d0 | 1 | 1 | ClCCl | 665 |
43,612 | 192,139 | 309,395 | [H-].[Na+].[CH3:3][CH:4]([O:7][C:8]1[CH:17]=[CH:16][C:11]([O:12][CH2:13][CH2:14][OH:15])=[CH:10][CH:9]=1)[CH2:5][CH3:6].[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21](F)[N:20]=1>C1COCC1.CN(P(N(C)C)(N(C)C)=O)C>[F:18][C:19]1[N:20]=[C:21]([O:15][CH2:14][CH2:13][O:12][C:11]2[CH:16]=[CH:17][C:8]([O:7][CH:4]([CH3:3])[CH2:5][CH3:6])=[CH:9][CH:10]=2)[CH:22]=[CH:23][CH:24]=1 | |f:0.1| | US05389651_ | 1,995 | C1CCOC1.CN(C)P(=O)(N(C)C)N(C)C.F[c:14]1[cH:15][cH:16][cH:17][c:18]([F:19])[n:20]1.[CH3:1][CH2:2][CH:3]([CH3:4])[O:5][c:6]1[cH:7][cH:8][c:9]([O:10][CH2:11][CH2:12][OH:13])[cH:21][cH:22]1.[H-].[Na+]>>[CH3:1][CH2:2][CH:3]([CH3:4])[O:5][c:6]1[cH:7][cH:8][c:9]([O:10][CH2:11][CH2:12][O:13][c:14]2[cH:15][cH:16][cH:17][c:18]([F:19])[n:20]2)[cH:21][cH:22]1 | 0.67907 | C1CCOC1.CCC(C)Oc1ccc(OCCO)cc1.CN(C)P(=O)(N(C)C)N(C)C.Fc1cccc(F)n1.[H-]~[Na+]>>CCC(C)Oc1ccc(OCCOc2cccc(F)n2)cc1 | C1CCOC1.CCC(C)Oc1ccc(OCCO)cc1.CN(C)P(=O)(N(C)C)N(C)C.Fc1cccc(F)n1.[H-].[Na+]>>CCC(C)Oc1ccc(OCCOc2cccc(F)n2)cc1 | US05389651_grants | e9734811903334325fa7c17cadc16eb462529f5aa53d1720c17e8b21 | C1CCOC1.CN(C)P(=O)(N(C)C)N(C)C.F[c:14]1[cH:15][cH:16][cH:17][c:18]([F:19])[n:20]1.[CH3:1][CH2:2][CH:3]([CH3:4])[O:5][c:6]1[cH:7][cH:8][c:9]([O:10][CH2:11][CH2:12][OH:13])[cH:21][cH:22]1.[H-].[Na+] | [CH3:1][CH2:2][CH:3]([CH3:4])[O:5][c:6]1[cH:7][cH:8][c:9]([O:10][CH2:11][CH2:12][O:13][c:14]2[cH:15][cH:16][cH:17][c:18]([F:19])[n:20]2)[cH:21][cH:22]1 | ([#7;a:2]:[c;H0;D3;+0:1](:[c:3])-[O;H0;D2;+0:5]-[C:4])>>(F-[c;H0;D3;+0:1](:[#7;a:2]):[c:3]).([C:4]-[OH;D1;+0:5]) | 4f4196eaedab9f578e0f926ce0f35097e0cee160f25356f5bf20e051 | 1 | 1 | C1CCOC1.CN(C)P(=O)(N(C)C)N(C)C.[H-].[Na+] | 541 |
299,014 | 973,816 | 1,639,687 | [Si:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=O)=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(Cl)(=O)C([Cl:22])=O>CN(C=O)C>[Si:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([Cl:22])=[O:18])=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2] | null | US09075058B2_0346 | 2,015 | CN(C)C=O.O=C(Cl)C(=O)[Cl:16].O[C:14]([CH2:13][c:12]1[cH:11][cH:10][c:9]([O:8][Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7])[cH:18][cH:17]1)=[O:15]>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][c:9]1[cH:10][cH:11][c:12]([CH2:13][C:14](=[O:15])[Cl:16])[cH:17][cH:18]1 | 0.244203 | CC(C)(C)[Si](C)(C)Oc1ccc(CC(=O)O)cc1.CN(C)C=O.O=C(Cl)C(=O)Cl>>CC(C)(C)[Si](C)(C)Oc1ccc(CC(=O)Cl)cc1 | CC(C)(C)[Si](C)(C)Oc1ccc(CC(=O)O)cc1.CN(C)C=O.O=C(Cl)C(=O)Cl>>CC(C)(C)[Si](C)(C)Oc1ccc(CC(=O)Cl)cc1 | US09075058B2_0346grants | bdc0a153cf9fa98921acb64e8eccf1b4c915ed63c0cecae99b18829c | CN(C)C=O.O=C(Cl)C(=O)[Cl:16].O[C:14]([CH2:13][c:12]1[cH:11][cH:10][c:9]([O:8][Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7])[cH:18][cH:17]1)=[O:15] | [CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][c:9]1[cH:10][cH:11][c:12]([CH2:13][C:14](=[O:15])[Cl:16])[cH:17][cH:18]1 | ([C:3]-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:4])>>(Cl-C(=O)-C(=O)-[Cl;H0;D1;+0:1]).(O-[C;H0;D3;+0:2](-[C:3])=[O;D1;H0:4]) | 78435edea32d2d38b5145914f27e36d7d5f382c893aab0d3c0c387d1 | 1 | 1 | CN(C)C=O | 56 |
272,212 | 893,195 | 1,489,209 | [Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:16]4[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=4[Cl:24])[CH2:12][CH2:13][CH2:14][CH2:15][N:7]3[C:6]=2[C:5]([CH2:25][OH:26])=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(#N)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:25]=[O:26])=[C:6]2[C:10]=1[N:9]=[C:8]1[N:11]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=3[Cl:24])[CH2:12][CH2:13][CH2:14][CH2:15][N:7]21 | null | US08785460B2_3145 | 2,014 | CC#N.CC(=O)OI1(OC(C)=O)(OC(C)=O)OC(=O)c2ccccc21.CCOC(C)=O.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][CH2:10][CH2:11][n:12]3[c:13]2[n:14][c:15]2[c:16]([Cl:17])[cH:18][cH:19][c:20]([CH2:21][OH:22])[c:23]32)[c:24]([Cl:25])[cH:26]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][CH2:10][CH2:11][n:12]3[c:13]2[n:14][c:15]2[c:16]([Cl:17])[cH:18][cH:19][c:20]([CH:21]=[O:22])[c:23]32)[c:24]([Cl:25])[cH:26]1 | 0.975367 | CC#N.CC(=O)OI1(OC(C)=O)(OC(C)=O)OC(=O)c2ccccc21.CCOC(C)=O.COc1ccc(N2CCCCn3c2nc2c(Cl)ccc(CO)c23)c(Cl)c1>>COc1ccc(N2CCCCn3c2nc2c(Cl)ccc(C=O)c23)c(Cl)c1 | CC#N.CC(=O)OI1(OC(C)=O)(OC(C)=O)OC(=O)c2ccccc21.CCOC(C)=O.COc1ccc(N2CCCCn3c2nc2c(Cl)ccc(CO)c23)c(Cl)c1>>COc1ccc(N2CCCCn3c2nc2c(Cl)ccc(C=O)c23)c(Cl)c1 | US08785460B2_3145grants | 2fdc8c2c5a88db0818301c532087dd4170c6e6019cba02ce4e76c0e1 | CC#N.CC(=O)OI1(OC(C)=O)(OC(C)=O)OC(=O)c2ccccc21.CCOC(C)=O.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][CH2:10][CH2:11][n:12]3[c:13]2[n:14][c:15]2[c:16]([Cl:17])[cH:18][cH:19][c:20]([CH2:21][OH:22])[c:23]32)[c:24]([Cl:25])[cH:26]1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][CH2:10][CH2:11][n:12]3[c:13]2[n:14][c:15]2[c:16]([Cl:17])[cH:18][cH:19][c:20]([CH:21]=[O:22])[c:23]32)[c:24]([Cl:25])[cH:26]1 | ([#7;a:1]:[c:2]:[c:3]-[CH;D2;+0:4]=[O;H0;D1;+0:5])>>([#7;a:1]:[c:2]:[c:3]-[CH2;D2;+0:4]-[OH;D1;+0:5]) | cfe281a75d1b2b2acde2ac44b3a8433d97f5dddc83d112a905a74a4c | 1 | 1 | CC#N.CC(=O)OI1(OC(C)=O)(OC(C)=O)OC(=O)c2ccccc21.CCOC(C)=O | 520 |
374,545 | 837,209 | null | [C:1]([C:4]1[CH:5]=[C:6]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:7]([OH:14])=[C:8]([C:12]=1[CH3:13])[C:9]([OH:11])=O)(=[O:3])[CH3:2].[CH3:19][O:20][C:21]1[CH:27]=[C:26]([S:28]([C:31]([F:34])([F:33])[F:32])(=[O:30])=[O:29])[CH:25]=[CH:24][C:22]=1[NH2:23]>>[C:1]([C:4]1[C:12]([CH3:13])=[C:8]([C:7]([OH:14])=[C:6]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:5]=1)[C:9]([NH:23][C:22]1[CH:24]=[CH:25][C:26]([S:28]([C:31]([F:32])([F:33])[F:34])(=[O:29])=[O:30])=[CH:27][C:21]=1[O:20][CH3:19])=[O:11])(=[O:3])[CH3:2] | null | US20100041657A1_0681 | 2,010 | O[C:17](=[O:18])[c:19]1[c:20]([CH3:21])[c:22]([C:23]([CH3:24])=[O:25])[cH:26][c:27]([C:28]([CH3:29])([CH3:30])[CH3:31])[c:32]1[OH:33].[CH3:1][O:2][c:3]1[cH:4][c:5]([S:6](=[O:7])(=[O:8])[C:9]([F:10])([F:11])[F:12])[cH:13][cH:14][c:15]1[NH2:16]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([S:6](=[O:7])(=[O:8])[C:9]([F:10])([F:11])[F:12])[cH:13][cH:14][c:15]1[NH:16][C:17](=[O:18])[c:19]1[c:20]([CH3:21])[c:22]([C:23]([CH3:24])=[O:25])[cH:26][c:27]([C:28]([CH3:29])([CH3:30])[CH3:31])[c:32]1[OH:33] | 0.063567 | CC(=O)c1cc(C(C)(C)C)c(O)c(C(=O)O)c1C.COc1cc(S(=O)(=O)C(F)(F)F)ccc1N>>COc1cc(S(=O)(=O)C(F)(F)F)ccc1NC(=O)c1c(C)c(C(C)=O)cc(C(C)(C)C)c1O | CC(=O)c1cc(C(C)(C)C)c(O)c(C(=O)O)c1C.COc1cc(S(=O)(=O)C(F)(F)F)ccc1N>>COc1cc(S(=O)(=O)C(F)(F)F)ccc1NC(=O)c1c(C)c(C(C)=O)cc(C(C)(C)C)c1O | US20100041657A1_0681apps | 71404d24dd33be4cdcf203c0b0798da2258a5d9b911ed1999e3a5452 | O[C:17](=[O:18])[c:19]1[c:20]([CH3:21])[c:22]([C:23]([CH3:24])=[O:25])[cH:26][c:27]([C:28]([CH3:29])([CH3:30])[CH3:31])[c:32]1[OH:33].[CH3:1][O:2][c:3]1[cH:4][c:5]([S:6](=[O:7])(=[O:8])[C:9]([F:10])([F:11])[F:12])[cH:13][cH:14][c:15]1[NH2:16] | [CH3:1][O:2][c:3]1[cH:4][c:5]([S:6](=[O:7])(=[O:8])[C:9]([F:10])([F:11])[F:12])[cH:13][cH:14][c:15]1[NH:16][C:17](=[O:18])[c:19]1[c:20]([CH3:21])[c:22]([C:23]([CH3:24])=[O:25])[cH:26][c:27]([C:28]([CH3:29])([CH3:30])[CH3:31])[c:32]1[OH:33] | ([O;D1;H0:2]=[C;H0;D3;+0:1](-[c:3])-[NH;D2;+0:4]-[c:5])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]).([NH2;D1;+0:4]-[c:5]) | 35b8cb0d38b7801143c15d7c216f0b66c154f00ac243d1252d6d0e55 | 1 | 1 | null | 50 |
215,887 | 726,792 | 1,197,332 | FC(F)(F)C(O)=O.[CH3:8][S:9]([C:12]1[CH:33]=[CH:32][C:15]([O:16][C:17]2[N:22]=[CH:21][N:20]=[C:19]3[N:23]([CH:26]4[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]4)[N:24]=[CH:25][C:18]=23)=[CH:14][CH:13]=1)(=[O:11])=[O:10].Cl[C:35]([O:37][CH2:38][CH3:39])=[O:36]>>[CH2:38]([O:37][C:35]([N:29]1[CH2:28][CH2:27][CH:26]([N:23]2[C:19]3=[N:20][CH:21]=[N:22][C:17]([O:16][C:15]4[CH:14]=[CH:13][C:12]([S:9]([CH3:8])(=[O:11])=[O:10])=[CH:33][CH:32]=4)=[C:18]3[CH:25]=[N:24]2)[CH2:31][CH2:30]1)=[O:36])[CH3:39] | |f:0.1| | US08188098B2_0273 | 2,012 | Cl[C:4]([O:3][CH2:2][CH3:1])=[O:5].O=C(O)C(F)(F)F.[NH:6]1[CH2:7][CH2:8][CH:9]([n:10]2[n:11][cH:12][c:13]3[c:14]([O:15][c:16]4[cH:17][cH:18][c:19]([S:20]([CH3:21])(=[O:22])=[O:23])[cH:24][cH:25]4)[n:26][cH:27][n:28][c:29]23)[CH2:30][CH2:31]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][CH:9]([n:10]2[n:11][cH:12][c:13]3[c:14]([O:15][c:16]4[cH:17][cH:18][c:19]([S:20]([CH3:21])(=[O:22])=[O:23])[cH:24][cH:25]4)[n:26][cH:27][n:28][c:29]23)[CH2:30][CH2:31]1 | 0.501618 | CCOC(=O)Cl.CS(=O)(=O)c1ccc(Oc2ncnc3c2cnn3C2CCNCC2)cc1~O=C(O)C(F)(F)F>>CCOC(=O)N1CCC(n2ncc3c(Oc4ccc(S(C)(=O)=O)cc4)ncnc32)CC1 | CCOC(=O)Cl.CS(=O)(=O)c1ccc(Oc2ncnc3c2cnn3C2CCNCC2)cc1.O=C(O)C(F)(F)F>>CCOC(=O)N1CCC(n2ncc3c(Oc4ccc(S(C)(=O)=O)cc4)ncnc32)CC1 | US08188098B2_0273grants | 31f424809bb6b7b25185749964b01dc67878341a2ee2351f20f13d1c | Cl[C:4]([O:3][CH2:2][CH3:1])=[O:5].O=C(O)C(F)(F)F.[NH:6]1[CH2:7][CH2:8][CH:9]([n:10]2[n:11][cH:12][c:13]3[c:14]([O:15][c:16]4[cH:17][cH:18][c:19]([S:20]([CH3:21])(=[O:22])=[O:23])[cH:24][cH:25]4)[n:26][cH:27][n:28][c:29]23)[CH2:30][CH2:31]1 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][CH:9]([n:10]2[n:11][cH:12][c:13]3[c:14]([O:15][c:16]4[cH:17][cH:18][c:19]([S:20]([CH3:21])(=[O:22])=[O:23])[cH:24][cH:25]4)[n:26][cH:27][n:28][c:29]23)[CH2:30][CH2:31]1 | ([#8:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[N;H0;D3;+0:5](-[C:4])-[C:6])>>(Cl-[C;H0;D3;+0:1](-[#8:2])=[O;D1;H0:3]).([C:4]-[NH;D2;+0:5]-[C:6]) | a8ad6d981577e38ffa105f9cec0abb9f8b4d3de801fd8006168b839b | 1 | 1 | O=C(O)C(F)(F)F | 219 |
156,147 | 554,720 | 927,179 | [C:1]([NH:9][CH2:10][C:11]1([C:17]([O:19]CC)=[O:18])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].O>C(O)C>[C:1]([NH:9][CH2:10][C:11]1([C:17]([OH:19])=[O:18])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1 | |f:1.2| | US07592453B2_0386 | 2,009 | CCO.CC[O:8][C:6]([C:5]1([CH2:4][NH:3][C:2](=[O:1])[c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1)=[O:7].O.[K+].[OH-]>>[O:1]=[C:2]([NH:3][CH2:4][C:5]1([C:6](=[O:7])[OH:8])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1)[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | 0.83351 | CCO.CCOC(=O)C1(CNC(=O)c2ccccc2)CCCCC1.O.[K+]~[OH-]>>O=C(NCC1(C(=O)O)CCCCC1)c1ccccc1 | CCO.CCOC(=O)C1(CNC(=O)c2ccccc2)CCCCC1.O.[K+].[OH-]>>O=C(NCC1(C(=O)O)CCCCC1)c1ccccc1 | US07592453B2_0386grants | b87eba52c4df2dbc3700da942f4529a75943bd719c87028703a1a91b | CCO.CC[O:8][C:6]([C:5]1([CH2:4][NH:3][C:2](=[O:1])[c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1)=[O:7].O.[K+].[OH-] | [O:1]=[C:2]([NH:3][CH2:4][C:5]1([C:6](=[O:7])[OH:8])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1)[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | ([C:5]-[C:4](-[C:6])(-[C:7])-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1])>>(C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4](-[C:5])(-[C:6])-[C:7]) | de1d17a26514ff71919036de3c5735d8feace13146a0176a2d5ae502 | 1 | 1 | CCO.O.[K+].[OH-] | 281 |
340,460 | 312,005 | null | [S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][C:18]3[CH:19]=[C:20]4[C:24](=[CH:25][CH:26]=3)[C:23]([CH3:28])([CH3:27])[CH:22]([NH:29][CH2:30][CH3:31])[CH2:21]4)[CH2:12][CH2:11]2)=[N:2]1.C(O[C:36](=[O:38])[CH3:37])(=O)C.C(N(CC)CC)C>C(Cl)Cl>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][C:18]3[CH:19]=[C:20]4[C:24](=[CH:25][CH:26]=3)[C:23]([CH3:28])([CH3:27])[CH:22]([N:29]([CH2:30][CH3:31])[C:36](=[O:38])[CH3:37])[CH2:21]4)[CH2:12][CH2:11]2)=[N:2]1 | null | US20050282819A1_0254 | 2,005 | CC(=O)O[C:4]([CH3:5])=[O:6].CCN(CC)CC.ClCCl.[CH3:1][CH2:2][NH:3][CH:7]1[CH2:8][c:9]2[cH:10][c:11]([CH2:12][CH2:13][N:14]3[CH2:15][CH2:16][N:17]([c:18]4[n:19][s:20][c:21]5[cH:22][cH:23][cH:24][cH:25][c:26]45)[CH2:27][CH2:28]3)[cH:29][cH:30][c:31]2[C:32]1([CH3:33])[CH3:34]>>[CH3:1][CH2:2][N:3]([C:4]([CH3:5])=[O:6])[CH:7]1[CH2:8][c:9]2[cH:10][c:11]([CH2:12][CH2:13][N:14]3[CH2:15][CH2:16][N:17]([c:18]4[n:19][s:20][c:21]5[cH:22][cH:23][cH:24][cH:25][c:26]45)[CH2:27][CH2:28]3)[cH:29][cH:30][c:31]2[C:32]1([CH3:33])[CH3:34] | 0.403341 | CC(=O)OC(C)=O.CCN(CC)CC.CCNC1Cc2cc(CCN3CCN(c4nsc5ccccc45)CC3)ccc2C1(C)C.ClCCl>>CCN(C(C)=O)C1Cc2cc(CCN3CCN(c4nsc5ccccc45)CC3)ccc2C1(C)C | CC(=O)OC(C)=O.CCN(CC)CC.CCNC1Cc2cc(CCN3CCN(c4nsc5ccccc45)CC3)ccc2C1(C)C.ClCCl>>CCN(C(C)=O)C1Cc2cc(CCN3CCN(c4nsc5ccccc45)CC3)ccc2C1(C)C | US20050282819A1_0254apps | 7950d82a9980a85752cead45f545b19abb9ae5c761b32b666d246880 | CC(=O)O[C:4]([CH3:5])=[O:6].CCN(CC)CC.ClCCl.[CH3:1][CH2:2][NH:3][CH:7]1[CH2:8][c:9]2[cH:10][c:11]([CH2:12][CH2:13][N:14]3[CH2:15][CH2:16][N:17]([c:18]4[n:19][s:20][c:21]5[cH:22][cH:23][cH:24][cH:25][c:26]45)[CH2:27][CH2:28]3)[cH:29][cH:30][c:31]2[C:32]1([CH3:33])[CH3:34] | [CH3:1][CH2:2][N:3]([C:4]([CH3:5])=[O:6])[CH:7]1[CH2:8][c:9]2[cH:10][c:11]([CH2:12][CH2:13][N:14]3[CH2:15][CH2:16][N:17]([c:18]4[n:19][s:20][c:21]5[cH:22][cH:23][cH:24][cH:25][c:26]45)[CH2:27][CH2:28]3)[cH:29][cH:30][c:31]2[C:32]1([CH3:33])[CH3:34] | ([C:4]-[N;H0;D3;+0:5](-[C:6])-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])>>(C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3]).([C:4]-[NH;D2;+0:5]-[C:6]) | 850466ba28e440ccfbe243813dd37fe45c414b2a9ee742dafad2e7ee | 1 | 1 | CCN(CC)CC.ClCCl | 369 |
167,192 | 587,772 | 975,627 | [C:1]([O:5][C:6](=[O:14])[NH:7][CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].Cl[C:16]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=[CH:18][N:17]=1>CN1C(=O)CCC1>[N+:22]([C:21]1[C:16]([N:11]2[CH2:12][CH2:13][CH:8]([NH:7][C:6](=[O:14])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:9][CH2:10]2)=[N:17][CH:18]=[CH:19][CH:20]=1)([O-:24])=[O:23] | null | US07709503B2_0732 | 2,010 | CN1CCCC1=O.Cl[c:13]1[n:14][cH:15][cH:16][cH:17][c:18]1[N+:19](=[O:20])[O-:21].[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH:9]1[CH2:10][CH2:11][NH:12][CH2:22][CH2:23]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH:9]1[CH2:10][CH2:11][N:12]([c:13]2[n:14][cH:15][cH:16][cH:17][c:18]2[N+:19](=[O:20])[O-:21])[CH2:22][CH2:23]1 | 0.399198 | CC(C)(C)OC(=O)NC1CCNCC1.CN1CCCC1=O.O=[N+]([O-])c1cccnc1Cl>>CC(C)(C)OC(=O)NC1CCN(c2ncccc2[N+](=O)[O-])CC1 | CC(C)(C)OC(=O)NC1CCNCC1.CN1CCCC1=O.O=[N+]([O-])c1cccnc1Cl>>CC(C)(C)OC(=O)NC1CCN(c2ncccc2[N+](=O)[O-])CC1 | US07709503B2_0732grants | 1fa7f68db9de00d7aabc8bbc0dff9952f8c3064308de87073d122f1b | CN1CCCC1=O.Cl[c:13]1[n:14][cH:15][cH:16][cH:17][c:18]1[N+:19](=[O:20])[O-:21].[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH:9]1[CH2:10][CH2:11][NH:12][CH2:22][CH2:23]1 | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH:9]1[CH2:10][CH2:11][N:12]([c:13]2[n:14][cH:15][cH:16][cH:17][c:18]2[N+:19](=[O:20])[O-:21])[CH2:22][CH2:23]1 | ([#7;a:2]:[c;H0;D3;+0:1](:[c:3])-[N;H0;D3;+0:5](-[C:4])-[C:6])>>(Cl-[c;H0;D3;+0:1](:[#7;a:2]):[c:3]).([C:4]-[NH;D2;+0:5]-[C:6]) | d775cf39c89817610201eb77d7f2c05750999ab6870ec4bcf35a0a78 | 1 | 1 | CN1CCCC1=O | 220 |
292,276 | 951,652 | 1,597,242 | [Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH:8]([OH:10])[CH3:9])[CH:3]=1.[S:11](Cl)([CH3:14])(=[O:13])=[O:12]>CN(C1C=CN=CC=1)C.ClCCl>[CH3:14][S:11]([O:10][CH:8]([C:4]1[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][N:5]=1)[CH3:9])(=[O:13])=[O:12] | null | US08987250B2_1531 | 2,015 | CN(C)c1ccncc1.ClCCl.Cl[S:4]([CH3:5])(=[O:6])=[O:7].[CH3:1][CH:2]([OH:3])[c:8]1[cH:9][c:10]([Br:11])[cH:12][cH:13][n:14]1>>[CH3:1][CH:2]([O:3][S:4]([CH3:5])(=[O:6])=[O:7])[c:8]1[cH:9][c:10]([Br:11])[cH:12][cH:13][n:14]1 | 0.548339 | CC(O)c1cc(Br)ccn1.CN(C)c1ccncc1.CS(=O)(=O)Cl.ClCCl>>CC(OS(C)(=O)=O)c1cc(Br)ccn1 | CC(O)c1cc(Br)ccn1.CN(C)c1ccncc1.CS(=O)(=O)Cl.ClCCl>>CC(OS(C)(=O)=O)c1cc(Br)ccn1 | US08987250B2_1531grants | b047de6fab31043fce952dd86ca058b604262ef49bf43cbc0dcc069f | CN(C)c1ccncc1.ClCCl.Cl[S:4]([CH3:5])(=[O:6])=[O:7].[CH3:1][CH:2]([OH:3])[c:8]1[cH:9][c:10]([Br:11])[cH:12][cH:13][n:14]1 | [CH3:1][CH:2]([O:3][S:4]([CH3:5])(=[O:6])=[O:7])[c:8]1[cH:9][c:10]([Br:11])[cH:12][cH:13][n:14]1 | ([C:5]-[O;H0;D2;+0:6]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4])>>(Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4]).([C:5]-[OH;D1;+0:6]) | 5b2ff2a69fb7bd6a032938e468684773bcc668928b037bbec0ac8335 | 1 | 1 | CN(C)c1ccncc1.ClCCl | 0 |
343,021 | 359,222 | null | [CH3:1][NH:2][C:3]([C@@H:5]([NH:17][C:18](=[O:42])[C@@H:19]([NH:26][C:27]([NH2:41])=[N:28][NH:29][C:30](=[O:40])[C@H:31]([NH2:39])[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:20][CH2:21][CH2:22][N+:23]([O-:25])=[O:24])[CH2:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=1)=[O:4].[C:43]([NH:46][C@@H:47]([CH2:51][C:52]1[CH:57]=[CH:56][C:55]([OH:58])=[CH:54][CH:53]=1)[C:48](O)=[O:49])(=[O:45])[CH3:44].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C>[CH3:1][NH:2][C:3]([C@@H:5]([NH:17][C:18](=[O:42])[C@@H:19]([NH:26][C:27]([NH2:41])=[N:28][NH:29][C:30](=[O:40])[C@H:31]([NH:39][C:48](=[O:49])[C@@H:47]([NH:46][C:43](=[O:45])[CH3:44])[CH2:51][C:52]1[CH:57]=[CH:56][C:55]([OH:58])=[CH:54][CH:53]=1)[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:20][CH2:21][CH2:22][N+:23]([O-:25])=[O:24])[CH2:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=1)=[O:4] | |f:2.3| | US20060128613A1_0294 | 2,006 | CCN(CC)CC.CN(C)C=O.F[P-](F)(F)(F)(F)F.O[C:43](=[O:44])[C@H:45]([CH2:46][c:47]1[cH:48][cH:49][c:50]([OH:51])[cH:52][cH:53]1)[NH:54][C:55]([CH3:56])=[O:57].[CH3:1][NH:2][C:3](=[O:4])[C@H:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[cH:16]1)[NH:17][C:18](=[O:19])[C@H:20]([CH2:21][CH2:22][CH2:23][N+:24](=[O:25])[O-:26])[NH:27][C:28]([NH2:29])=[N:30][NH:31][C:32](=[O:33])[C@@H:34]([CH2:35][c:36]1[cH:37][cH:38][cH:39][cH:40][cH:41]1)[NH2:42].c1ccc2c(c1)nnn2O[P+](N1CCCC1)(N1CCCC1)N1CCCC1>>[CH3:1][NH:2][C:3](=[O:4])[C@H:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[cH:16]1)[NH:17][C:18](=[O:19])[C@H:20]([CH2:21][CH2:22][CH2:23][N+:24](=[O:25])[O-:26])[NH:27][C:28]([NH2:29])=[N:30][NH:31][C:32](=[O:33])[C@@H:34]([CH2:35][c:36]1[cH:37][cH:38][cH:39][cH:40][cH:41]1)[NH:42][C:43](=[O:44])[C@H:45]([CH2:46][c:47]1[cH:48][cH:49][c:50]([OH:51])[cH:52][cH:53]1)[NH:54][C:55]([CH3:56])=[O:57] | 0.82211 | CC(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)O.CCN(CC)CC.CN(C)C=O.CNC(=O)[C@H](Cc1ccc2ccccc2c1)NC(=O)[C@H](CCC[N+](=O)[O-])NC(N)=NNC(=O)[C@H](N)Cc1ccccc1.F[P-](F)(F)(F)(F)F~c1ccc2c(c1)nnn2O[P+](N1CCCC1)(N1CCCC1)N1CCCC1>>CNC(=O)[C@H](Cc1ccc2ccccc2c1)NC(=O)[C@H](CCC[N+](=O)[O-])NC(N)=NNC(=O)[C@@H](Cc1ccccc1)NC(=O)[C@H](Cc1ccc(O)cc1)NC(C)=O | CC(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)O.CCN(CC)CC.CN(C)C=O.CNC(=O)[C@H](Cc1ccc2ccccc2c1)NC(=O)[C@H](CCC[N+](=O)[O-])NC(N)=NNC(=O)[C@H](N)Cc1ccccc1.F[P-](F)(F)(F)(F)F.c1ccc2c(c1)nnn2O[P+](N1CCCC1)(N1CCCC1)N1CCCC1>>CNC(=O)[C@H](Cc1ccc2ccccc2c1)NC(=O)[C@H](CCC[N+](=O)[O-])NC(N)=NNC(=O)[C@@H](Cc1ccccc1)NC(=O)[C@H](Cc1ccc(O)cc1)NC(C)=O | US20060128613A1_0294apps | b83bd3c8dc04fdd1c25ef5f02abcaee75025c047051fcc8857331630 | CCN(CC)CC.CN(C)C=O.F[P-](F)(F)(F)(F)F.O[C:43](=[O:44])[C@H:45]([CH2:46][c:47]1[cH:48][cH:49][c:50]([OH:51])[cH:52][cH:53]1)[NH:54][C:55]([CH3:56])=[O:57].[CH3:1][NH:2][C:3](=[O:4])[C@H:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[cH:16]1)[NH:17][C:18](=[O:19])[C@H:20]([CH2:21][CH2:22][CH2:23][N+:24](=[O:25])[O-:26])[NH:27][C:28]([NH2:29])=[N:30][NH:31][C:32](=[O:33])[C@@H:34]([CH2:35][c:36]1[cH:37][cH:38][cH:39][cH:40][cH:41]1)[NH2:42].c1ccc2c(c1)nnn2O[P+](N1CCCC1)(N1CCCC1)N1CCCC1 | [CH3:1][NH:2][C:3](=[O:4])[C@H:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[cH:16]1)[NH:17][C:18](=[O:19])[C@H:20]([CH2:21][CH2:22][CH2:23][N+:24](=[O:25])[O-:26])[NH:27][C:28]([NH2:29])=[N:30][NH:31][C:32](=[O:33])[C@@H:34]([CH2:35][c:36]1[cH:37][cH:38][cH:39][cH:40][cH:41]1)[NH:42][C:43](=[O:44])[C@H:45]([CH2:46][c:47]1[cH:48][cH:49][c:50]([OH:51])[cH:52][cH:53]1)[NH:54][C:55]([CH3:56])=[O:57] | ([#7:4]-[C:5](=[O;D1;H0:6])-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3])>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([#7:4]-[C:5](=[O;D1;H0:6])-[C:7]-[NH2;D1;+0:8]) | 09e961e4c21b1adcf2f8d3b116773699ab5020ae114ca5b853caf10a | 0.333333 | 3 | CCN(CC)CC.CN(C)C=O.F[P-](F)(F)(F)(F)F.c1ccc2c(c1)nnn2O[P+](N1CCCC1)(N1CCCC1)N1CCCC1 | 133 |
126,631 | 465,983 | 788,914 | [F:1][C:2]([F:25])([F:24])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]=[C:12]([C:14]3[CH:23]=[CH:22][C:17]([C:18]([O:20]C)=[O:19])=[CH:16][CH:15]=3)[O:11][N:10]=2)=[CH:5][CH:4]=1.[OH-].[Na+].O1CCCC1.Cl>CO>[F:25][C:2]([F:1])([F:24])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]=[C:12]([C:14]3[CH:23]=[CH:22][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=3)[O:11][N:10]=2)=[CH:5][CH:4]=1 | |f:1.2| | US07223791B2_0452 | 2,007 | C1CCOC1.CO.C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7](-[c:8]2[n:9][c:10](-[c:11]3[cH:12][cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][cH:20]3)[n:21][o:22]2)[cH:23][cH:24]1.Cl.[Na+].[OH-]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7](-[c:8]2[n:9][c:10](-[c:11]3[cH:12][cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][cH:20]3)[n:21][o:22]2)[cH:23][cH:24]1 | 0.231065 | C1CCOC1.CO.COC(=O)c1ccc(-c2nc(-c3ccc(C(F)(F)F)cc3)no2)cc1.Cl.[Na+]~[OH-]>>O=C(O)c1ccc(-c2nc(-c3ccc(C(F)(F)F)cc3)no2)cc1 | C1CCOC1.CO.COC(=O)c1ccc(-c2nc(-c3ccc(C(F)(F)F)cc3)no2)cc1.Cl.[Na+].[OH-]>>O=C(O)c1ccc(-c2nc(-c3ccc(C(F)(F)F)cc3)no2)cc1 | US07223791B2_0452grants | 6ce6369a27ee60b2ed57e42eb6f3344c71840d6f4624f7eeb8a54042 | C1CCOC1.CO.C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7](-[c:8]2[n:9][c:10](-[c:11]3[cH:12][cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][cH:20]3)[n:21][o:22]2)[cH:23][cH:24]1.Cl.[Na+].[OH-] | [O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7](-[c:8]2[n:9][c:10](-[c:11]3[cH:12][cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][cH:20]3)[n:21][o:22]2)[cH:23][cH:24]1 | ([O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4]1:[c:5]:[c:6]:[c:7]:[c:8]:[c:9]:1)>>(C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[c:5]:[c:6]:[c:7]:[c:8]:[c:9]:1) | 48f3c58ed4b2eb976195200c79ebaafb36d7eb1c6248c7c6424a4457 | 1 | 1 | C1CCOC1.CO.Cl.[Na+].[OH-] | 247 |
304,300 | 988,948 | 1,668,014 | [Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][N:13]=2)[CH:11]=1)[C:5]([O:7]C)=[O:6].[OH-].[Li+]>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][N:13]=2)[CH:11]=1)[C:5]([OH:7])=[O:6] | |f:1.2| | US09133122B2_0920 | 2,015 | C1CCOC1.C[O:14][C:12]([c:11]1[cH:10][c:8]([Br:9])[cH:7][c:6](-[c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:17][n:16]2)[cH:15]1)=[O:13].[Li+].[OH-]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8]([Br:9])[cH:10][c:11]([C:12](=[O:13])[OH:14])[cH:15]2)[n:16][cH:17]1 | 0.960951 | C1CCOC1.COC(=O)c1cc(Br)cc(-c2ccc(C)cn2)c1.[Li+]~[OH-]>>Cc1ccc(-c2cc(Br)cc(C(=O)O)c2)nc1 | C1CCOC1.COC(=O)c1cc(Br)cc(-c2ccc(C)cn2)c1.[Li+].[OH-]>>Cc1ccc(-c2cc(Br)cc(C(=O)O)c2)nc1 | US09133122B2_0920grants | 9422daf8a73406a1a20ff2f33a447008fe3a6b5800b95cf7741a375b | C1CCOC1.C[O:14][C:12]([c:11]1[cH:10][c:8]([Br:9])[cH:7][c:6](-[c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:17][n:16]2)[cH:15]1)=[O:13].[Li+].[OH-] | [CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8]([Br:9])[cH:10][c:11]([C:12](=[O:13])[OH:14])[cH:15]2)[n:16][cH:17]1 | ([O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4]1:[c:5]:[c:6]:[c:7]:[c:8]:[c:9]:1)>>(C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[c:5]:[c:6]:[c:7]:[c:8]:[c:9]:1) | 48f3c58ed4b2eb976195200c79ebaafb36d7eb1c6248c7c6424a4457 | 1 | 1 | C1CCOC1.[Li+].[OH-] | 247 |
206,175 | 699,264 | 1,151,735 | F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[C:25]([O:29][C:30]([NH:32][C:33]1([C:48](O)=[O:49])[CH2:38][CH2:37][N:36]([C:39]2[C:40]3[CH:47]=[CH:46][NH:45][C:41]=3[N:42]=[CH:43][N:44]=2)[CH2:35][CH2:34]1)=[O:31])([CH3:28])([CH3:27])[CH3:26].C(N(CC)C(C)C)(C)C.[NH2:60][C@H:61]([C:67]1[CH:72]=[CH:71][C:70]([Cl:73])=[CH:69][CH:68]=1)[CH2:62][C:63]([O:65][CH3:66])=[O:64]>CN1C(=O)CCC1.CCOC(C)=O>[C:25]([O:29][C:30]([NH:32][C:33]1([C:48]([NH:60][C@H:61]([C:67]2[CH:68]=[CH:69][C:70]([Cl:73])=[CH:71][CH:72]=2)[CH2:62][C:63]([O:65][CH3:66])=[O:64])=[O:49])[CH2:38][CH2:37][N:36]([C:39]2[C:40]3[CH:47]=[CH:46][NH:45][C:41]=3[N:42]=[CH:43][N:44]=2)[CH2:35][CH2:34]1)=[O:31])([CH3:26])([CH3:28])[CH3:27] | |f:0.1| | US08101623B2_0476 | 2,012 | CCN(C(C)C)C(C)C.CCOC(C)=O.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN1CCCC1=O.F[P-](F)(F)(F)(F)F.O[C:8](=[O:9])[C:10]1([NH:11][C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20][N:21]([c:22]2[n:23][cH:24][n:25][c:26]3[nH:27][cH:28][cH:29][c:30]23)[CH2:31][CH2:32]1.[CH3:1][O:2][C:3](=[O:4])[CH2:5][C@H:6]([NH2:7])[c:33]1[cH:34][cH:35][c:36]([Cl:37])[cH:38][cH:39]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][C@H:6]([NH:7][C:8](=[O:9])[C:10]1([NH:11][C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20][N:21]([c:22]2[n:23][cH:24][n:25][c:26]3[nH:27][cH:28][cH:29][c:30]23)[CH2:31][CH2:32]1)[c:33]1[cH:34][cH:35][c:36]([Cl:37])[cH:38][cH:39]1 | 0.35766 | CC(C)(C)OC(=O)NC1(C(=O)O)CCN(c2ncnc3[nH]ccc23)CC1.CCN(C(C)C)C(C)C.CCOC(C)=O.CN(C)C(On1nnc2cccnc21)=[N+](C)C~F[P-](F)(F)(F)(F)F.CN1CCCC1=O.COC(=O)C[C@H](N)c1ccc(Cl)cc1>>COC(=O)C[C@H](NC(=O)C1(NC(=O)OC(C)(C)C)CCN(c2ncnc3[nH]ccc23)CC1)c1ccc(Cl)cc1 | CC(C)(C)OC(=O)NC1(C(=O)O)CCN(c2ncnc3[nH]ccc23)CC1.CCN(C(C)C)C(C)C.CCOC(C)=O.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN1CCCC1=O.COC(=O)C[C@H](N)c1ccc(Cl)cc1.F[P-](F)(F)(F)(F)F>>COC(=O)C[C@H](NC(=O)C1(NC(=O)OC(C)(C)C)CCN(c2ncnc3[nH]ccc23)CC1)c1ccc(Cl)cc1 | US08101623B2_0476grants | 325656596993ec0166848fde1edba04a77b15300a88ea5adac1960e9 | CCN(C(C)C)C(C)C.CCOC(C)=O.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN1CCCC1=O.F[P-](F)(F)(F)(F)F.O[C:8](=[O:9])[C:10]1([NH:11][C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20][N:21]([c:22]2[n:23][cH:24][n:25][c:26]3[nH:27][cH:28][cH:29][c:30]23)[CH2:31][CH2:32]1.[CH3:1][O:2][C:3](=[O:4])[CH2:5][C@H:6]([NH2:7])[c:33]1[cH:34][cH:35][c:36]([Cl:37])[cH:38][cH:39]1 | [CH3:1][O:2][C:3](=[O:4])[CH2:5][C@H:6]([NH:7][C:8](=[O:9])[C:10]1([NH:11][C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20][N:21]([c:22]2[n:23][cH:24][n:25][c:26]3[nH:27][cH:28][cH:29][c:30]23)[CH2:31][CH2:32]1)[c:33]1[cH:34][cH:35][c:36]([Cl:37])[cH:38][cH:39]1 | ([C:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[C:5]-[c:6]1:[c:7]:[c:8]:[c:9]:[c:10]:[c:11]:1)>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([NH2;D1;+0:4]-[C:5]-[c:6]1:[c:7]:[c:8]:[c:9]:[c:10]:[c:11]:1) | 5ad7c2cc16d6ee5b57312b54d1398a8d361f2cfad0dc66add676f018 | 1 | 1 | CCN(C(C)C)C(C)C.CCOC(C)=O.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN1CCCC1=O.F[P-](F)(F)(F)(F)F | 599 |
389,098 | 1,103,338 | null | [Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[C:3]=1[OH:14].[F:15][C:16]([F:29])([F:28])[S:17](O[S:17]([C:16]([F:29])([F:28])[F:15])(=[O:19])=[O:18])(=[O:19])=[O:18]>N1C=CC=CC=1>[F:15][C:16]([F:29])([F:28])[S:17]([O:14][C:3]1[C:4]([C:8]2[CH:9]=[CH:10][N:11]=[CH:12][CH:13]=2)=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])(=[O:19])=[O:18] | null | US20110224204A1_0362 | 2,011 | O=S(=O)(O[S:2](=[O:1])(=[O:3])[C:18]([F:19])([F:20])[F:21])C(F)(F)F.[OH:4][c:5]1[c:6]([Cl:7])[cH:8][cH:9][cH:10][c:11]1-[c:12]1[cH:13][cH:14][n:15][cH:16][cH:17]1.c1ccncc1>>[O:1]=[S:2](=[O:3])([O:4][c:5]1[c:6]([Cl:7])[cH:8][cH:9][cH:10][c:11]1-[c:12]1[cH:13][cH:14][n:15][cH:16][cH:17]1)[C:18]([F:19])([F:20])[F:21] | 0.128765 | O=S(=O)(OS(=O)(=O)C(F)(F)F)C(F)(F)F.Oc1c(Cl)cccc1-c1ccncc1.c1ccncc1>>O=S(=O)(Oc1c(Cl)cccc1-c1ccncc1)C(F)(F)F | O=S(=O)(OS(=O)(=O)C(F)(F)F)C(F)(F)F.Oc1c(Cl)cccc1-c1ccncc1.c1ccncc1>>O=S(=O)(Oc1c(Cl)cccc1-c1ccncc1)C(F)(F)F | US20110224204A1_0362apps | d54563474dc5cf43e4182e77097095ed6146ea4e9beff5dbc54bfd2b | O=S(=O)(O[S:2](=[O:1])(=[O:3])[C:18]([F:19])([F:20])[F:21])C(F)(F)F.[OH:4][c:5]1[c:6]([Cl:7])[cH:8][cH:9][cH:10][c:11]1-[c:12]1[cH:13][cH:14][n:15][cH:16][cH:17]1.c1ccncc1 | [O:1]=[S:2](=[O:3])([O:4][c:5]1[c:6]([Cl:7])[cH:8][cH:9][cH:10][c:11]1-[c:12]1[cH:13][cH:14][n:15][cH:16][cH:17]1)[C:18]([F:19])([F:20])[F:21] | ([F;D1;H0:5]-[C:4](-[F;D1;H0:6])(-[F;D1;H0:7])-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[O;H0;D2;+0:8]-[c:9])>>(F-C(-F)(-F)-S(=O)(=O)-O-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[F;D1;H0:7]).([OH;D1;+0:8]-[c:9]) | 99db519e153161d9e1a0b089bc1dd8038bb89ab236fbb46bac2ac4f7 | 1 | 1 | c1ccncc1 | 731 |
323,041 | 1,049,940 | 1,781,745 | [CH3:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].CCN(C(C)C)C(C)C.[F:21][C:22]([F:33])([F:32])[C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26](Cl)=[O:27]>ClCCl>[CH3:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:26](=[O:27])[C:25]2[CH:29]=[CH:30][CH:31]=[C:23]([C:22]([F:21])([F:32])[F:33])[CH:24]=2)=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10] | null | US09388165B2_0161 | 2,016 | CCN(C(C)C)C(C)C.ClCCl.Cl[C:7](=[O:8])[c:9]1[cH:10][cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18]1.[CH3:1][c:2]1[cH:3][cH:4][c:5]([NH2:6])[cH:19][c:20]1[N+:21](=[O:22])[O-:23]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([NH:6][C:7](=[O:8])[c:9]2[cH:10][cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18]2)[cH:19][c:20]1[N+:21](=[O:22])[O-:23] | 0.247562 | CCN(C(C)C)C(C)C.Cc1ccc(N)cc1[N+](=O)[O-].ClCCl.O=C(Cl)c1cccc(C(F)(F)F)c1>>Cc1ccc(NC(=O)c2cccc(C(F)(F)F)c2)cc1[N+](=O)[O-] | CCN(C(C)C)C(C)C.Cc1ccc(N)cc1[N+](=O)[O-].ClCCl.O=C(Cl)c1cccc(C(F)(F)F)c1>>Cc1ccc(NC(=O)c2cccc(C(F)(F)F)c2)cc1[N+](=O)[O-] | US09388165B2_0161grants | ba09ae1a99b10c2fb2862a71c18d983826841fab8b3aedc1e16cf88a | CCN(C(C)C)C(C)C.ClCCl.Cl[C:7](=[O:8])[c:9]1[cH:10][cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18]1.[CH3:1][c:2]1[cH:3][cH:4][c:5]([NH2:6])[cH:19][c:20]1[N+:21](=[O:22])[O-:23] | [CH3:1][c:2]1[cH:3][cH:4][c:5]([NH:6][C:7](=[O:8])[c:9]2[cH:10][cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18]2)[cH:19][c:20]1[N+:21](=[O:22])[O-:23] | ([O;D1;H0:2]=[C;H0;D3;+0:1](-[c:3])-[NH;D2;+0:4]-[c:5])>>(Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]).([NH2;D1;+0:4]-[c:5]) | 81bbe9d480d200be1437e9ca625a57474abf80dfdc397cf8e383daca | 1 | 1 | CCN(C(C)C)C(C)C.ClCCl | 11 |
42,901 | 189,137 | 304,419 | [F:1][C:2]1[CH:21]=[CH:20][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][N:12]([CH2:15][C@@H:16]([CH3:19])[CH2:17][OH:18])[CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1.C(N(CC)CC)C.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>C(Cl)Cl>[CH3:29][S:30]([O:18][CH2:17][C@H:16]([CH3:19])[CH2:15][N:12]1[CH2:13][CH2:14][CH:9]([C:6]2[C:5]3[CH:20]=[CH:21][C:2]([F:1])=[CH:3][C:4]=3[O:8][N:7]=2)[CH2:10][CH2:11]1)(=[O:32])=[O:31] | null | US05364866_ | 1,994 | CCN(CC)CC.ClCCl.Cl[S:5]([CH3:6])(=[O:7])=[O:8].[CH3:1][C@@H:2]([CH2:3][OH:4])[CH2:9][N:10]1[CH2:11][CH2:12][CH:13]([c:14]2[n:15][o:16][c:17]3[cH:18][c:19]([F:20])[cH:21][cH:22][c:23]23)[CH2:24][CH2:25]1>>[CH3:1][C@@H:2]([CH2:3][O:4][S:5]([CH3:6])(=[O:7])=[O:8])[CH2:9][N:10]1[CH2:11][CH2:12][CH:13]([c:14]2[n:15][o:16][c:17]3[cH:18][c:19]([F:20])[cH:21][cH:22][c:23]23)[CH2:24][CH2:25]1 | 0.62228 | CCN(CC)CC.CS(=O)(=O)Cl.C[C@@H](CO)CN1CCC(c2noc3cc(F)ccc23)CC1.ClCCl>>C[C@@H](COS(C)(=O)=O)CN1CCC(c2noc3cc(F)ccc23)CC1 | CCN(CC)CC.CS(=O)(=O)Cl.C[C@@H](CO)CN1CCC(c2noc3cc(F)ccc23)CC1.ClCCl>>C[C@@H](COS(C)(=O)=O)CN1CCC(c2noc3cc(F)ccc23)CC1 | US05364866_grants | 25dd209afea65f34ce339e0cbdb0cd77eb002658dfa4bf96c42a7ae8 | CCN(CC)CC.ClCCl.Cl[S:5]([CH3:6])(=[O:7])=[O:8].[CH3:1][C@@H:2]([CH2:3][OH:4])[CH2:9][N:10]1[CH2:11][CH2:12][CH:13]([c:14]2[n:15][o:16][c:17]3[cH:18][c:19]([F:20])[cH:21][cH:22][c:23]23)[CH2:24][CH2:25]1 | [CH3:1][C@@H:2]([CH2:3][O:4][S:5]([CH3:6])(=[O:7])=[O:8])[CH2:9][N:10]1[CH2:11][CH2:12][CH:13]([c:14]2[n:15][o:16][c:17]3[cH:18][c:19]([F:20])[cH:21][cH:22][c:23]23)[CH2:24][CH2:25]1 | ([C:5]-[O;H0;D2;+0:6]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4])>>(Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4]).([C:5]-[OH;D1;+0:6]) | 5b2ff2a69fb7bd6a032938e468684773bcc668928b037bbec0ac8335 | 1 | 1 | CCN(CC)CC.ClCCl | 0 |
119,806 | 445,173 | 756,209 | [C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([NH2:15])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22](O)=[O:23])[CH:17]=1.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(=O)([O-])O.[Na+]>CN(C)C=O>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:10][CH2:11][C@H:12]([NH:15][C:22]([C:18]2[CH:17]=[N:16][CH:21]=[CH:20][CH:19]=2)=[O:23])[CH2:13][CH2:14]1)=[O:7])([CH3:4])([CH3:2])[CH3:3] | |f:4.5| | US07138397B2_0388 | 2,006 | CCN=C=NCCCN(C)C.CN(C)C=O.O=C([O-])O.O[C:14](=[O:15])[c:16]1[cH:17][cH:18][cH:19][n:20][cH:21]1.On1nnc2ccccc21.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:10][CH2:11][C@H:12]([NH2:13])[CH2:22][CH2:23]1.[Na+]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:10][CH2:11][C@H:12]([NH:13][C:14](=[O:15])[c:16]2[cH:17][cH:18][cH:19][n:20][cH:21]2)[CH2:22][CH2:23]1 | 0.335038 | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](N)CC1.CCN=C=NCCCN(C)C.CN(C)C=O.O=C(O)c1cccnc1.O=C([O-])O~[Na+].On1nnc2ccccc21>>CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](NC(=O)c2cccnc2)CC1 | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](N)CC1.CCN=C=NCCCN(C)C.CN(C)C=O.O=C(O)c1cccnc1.O=C([O-])O.On1nnc2ccccc21.[Na+]>>CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](NC(=O)c2cccnc2)CC1 | US07138397B2_0388grants | e01da4b32f9a0fab997a2a83e5b7f95e54227646463dceb343686dfe | CCN=C=NCCCN(C)C.CN(C)C=O.O=C([O-])O.O[C:14](=[O:15])[c:16]1[cH:17][cH:18][cH:19][n:20][cH:21]1.On1nnc2ccccc21.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:10][CH2:11][C@H:12]([NH2:13])[CH2:22][CH2:23]1.[Na+] | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:10][CH2:11][C@H:12]([NH:13][C:14](=[O:15])[c:16]2[cH:17][cH:18][cH:19][n:20][cH:21]2)[CH2:22][CH2:23]1 | ([#7;a:5]:[c:4]:[c:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]:[c:4]:[#7;a:5]).([C:6]-[NH2;D1;+0:7]) | c8d3e8be644ca37fe3075935d6d9f9515443e1dc5a5fca512a1988ac | 1 | 1 | CCN=C=NCCCN(C)C.CN(C)C=O.O=C([O-])O.On1nnc2ccccc21.[Na+] | 674 |
30,103 | 138,315 | 222,747 | [NH:1]([C:62]([O:64][C:65]([CH3:68])([CH3:67])[CH3:66])=[O:63])[C@H:2]([C:4]([NH:6][CH2:7][C:8]([NH:10][C@H:11]([C:15]([N:17]1[CH2:61][CH2:60][CH2:59][C@H:18]1[C:19]([NH:21][CH2:22][C:23]([NH:25][C@H:26]([C:34]([NH:36][CH2:37][C:38]([NH:40][C@H:41]([C:45]([NH:47][CH2:48][C:49]([O:51]CC1C=CC=CC=1)=[O:50])=[O:46])[CH:42]([CH3:44])[CH3:43])=[O:39])=[O:35])[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:24])=[O:20])=[O:16])[CH:12]([CH3:14])[CH3:13])=[O:9])=[O:5])[CH3:3].N(C(OC(C)(C)C)=O)[C@H](C(NCC(O)=O)=O)C>O>[NH:1]([C:62]([O:64][C:65]([CH3:68])([CH3:67])[CH3:66])=[O:63])[C@H:2]([C:4]([NH:6][CH2:7][C:8]([NH:10][C@H:11]([C:15]([N:17]1[CH2:61][CH2:60][CH2:59][C@H:18]1[C:19]([NH:21][CH2:22][C:23]([NH:25][C@H:26]([C:34]([NH:36][CH2:37][C:38]([NH:40][C@H:41]([C:45]([NH:47][CH2:48][C:49]([OH:51])=[O:50])=[O:46])[CH:42]([CH3:43])[CH3:44])=[O:39])=[O:35])[CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:24])=[O:20])=[O:16])[CH:12]([CH3:13])[CH3:14])=[O:9])=[O:5])[CH3:3] | null | US04976734_ | 1,990 | C[C@H](NC(=O)OC(C)(C)C)C(=O)NCC(=O)O.O.c1ccc(C[O:61][C:59]([CH2:58][NH:57][C:55]([C@H:4]([CH:2]([CH3:1])[CH3:3])[NH:5][C:6](=[O:7])[CH2:8][NH:9][C:10](=[O:11])[C@H:12]([CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[NH:20][C:21](=[O:22])[CH2:23][NH:24][C:25](=[O:26])[C@@H:27]2[CH2:28][CH2:29][CH2:30][N:31]2[C:32](=[O:33])[C@@H:34]([NH:35][C:36](=[O:37])[CH2:38][NH:39][C:40](=[O:41])[C@H:42]([CH3:43])[NH:44][C:45](=[O:46])[O:47][C:48]([CH3:49])([CH3:50])[CH3:51])[CH:52]([CH3:53])[CH3:54])=[O:56])=[O:60])cc1>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[CH2:8][NH:9][C:10](=[O:11])[C@H:12]([CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)[NH:20][C:21](=[O:22])[CH2:23][NH:24][C:25](=[O:26])[C@@H:27]1[CH2:28][CH2:29][CH2:30][N:31]1[C:32](=[O:33])[C@@H:34]([NH:35][C:36](=[O:37])[CH2:38][NH:39][C:40](=[O:41])[C@H:42]([CH3:43])[NH:44][C:45](=[O:46])[O:47][C:48]([CH3:49])([CH3:50])[CH3:51])[CH:52]([CH3:53])[CH3:54])[C:55](=[O:56])[NH:57][CH2:58][C:59](=[O:60])[OH:61] | 0.174632 | CC(C)[C@H](NC(=O)CNC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)CNC(=O)[C@H](C)NC(=O)OC(C)(C)C)C(C)C)C(=O)NCC(=O)OCc1ccccc1.C[C@H](NC(=O)OC(C)(C)C)C(=O)NCC(=O)O.O>>CC(C)[C@H](NC(=O)CNC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)CNC(=O)[C@H](C)NC(=O)OC(C)(C)C)C(C)C)C(=O)NCC(=O)O | CC(C)[C@H](NC(=O)CNC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)CNC(=O)[C@H](C)NC(=O)OC(C)(C)C)C(C)C)C(=O)NCC(=O)OCc1ccccc1.C[C@H](NC(=O)OC(C)(C)C)C(=O)NCC(=O)O.O>>CC(C)[C@H](NC(=O)CNC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)CNC(=O)[C@H](C)NC(=O)OC(C)(C)C)C(C)C)C(=O)NCC(=O)O | US04976734_grants | 15dffc22d48673bd8fb7d7384f337f84b427c8daf015e30b1e5db3ce | C[C@H](NC(=O)OC(C)(C)C)C(=O)NCC(=O)O.O.c1ccc(C[O:61][C:59]([CH2:58][NH:57][C:55]([C@H:4]([CH:2]([CH3:1])[CH3:3])[NH:5][C:6](=[O:7])[CH2:8][NH:9][C:10](=[O:11])[C@H:12]([CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[NH:20][C:21](=[O:22])[CH2:23][NH:24][C:25](=[O:26])[C@@H:27]2[CH2:28][CH2:29][CH2:30][N:31]2[C:32](=[O:33])[C@@H:34]([NH:35][C:36](=[O:37])[CH2:38][NH:39][C:40](=[O:41])[C@H:42]([CH3:43])[NH:44][C:45](=[O:46])[O:47][C:48]([CH3:49])([CH3:50])[CH3:51])[CH:52]([CH3:53])[CH3:54])=[O:56])=[O:60])cc1 | [CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[CH2:8][NH:9][C:10](=[O:11])[C@H:12]([CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)[NH:20][C:21](=[O:22])[CH2:23][NH:24][C:25](=[O:26])[C@@H:27]1[CH2:28][CH2:29][CH2:30][N:31]1[C:32](=[O:33])[C@@H:34]([NH:35][C:36](=[O:37])[CH2:38][NH:39][C:40](=[O:41])[C@H:42]([CH3:43])[NH:44][C:45](=[O:46])[O:47][C:48]([CH3:49])([CH3:50])[CH3:51])[CH:52]([CH3:53])[CH3:54])[C:55](=[O:56])[NH:57][CH2:58][C:59](=[O:60])[OH:61] | ([C:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4])>>([C:1]-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-C-c1:c:c:c:c:c:1) | 3358e9d74bcf91ba7e96568094da103c2e3a143a7d89e0937034db20 | 1 | 1 | C[C@H](NC(=O)OC(C)(C)C)C(=O)NCC(=O)O.O | 186 |
77,958 | 316,007 | 536,118 | C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.BrN1C(=O)CCC1=O.[Br:28][C:29]1[CH:30]=[C:31]([CH:39]([CH2:43][CH:44]2[CH2:48][CH2:47][CH2:46][CH2:45]2)[C:40]([OH:42])=O)[CH:32]=[CH:33][C:34]=1[S:35]([CH3:38])(=[O:37])=[O:36].[NH2:49][C:50]1[S:51][CH:52]=[CH:53][N:54]=1>C(Cl)Cl>[Br:28][C:29]1[CH:30]=[C:31]([CH:39]([CH2:43][CH:44]2[CH2:48][CH2:47][CH2:46][CH2:45]2)[C:40]([NH:49][C:50]2[S:51][CH:52]=[CH:53][N:54]=2)=[O:42])[CH:32]=[CH:33][C:34]=1[S:35]([CH3:38])(=[O:36])=[O:37] | null | US06320050B1_ | 2,001 | ClCCl.O=C1CCC(=O)N1Br.O[C:16]([CH:9]([c:8]1[cH:7][cH:6][c:5]([S:2]([CH3:1])(=[O:3])=[O:4])[c:25]([Br:26])[cH:24]1)[CH2:10][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15]1)=[O:17].[NH2:18][c:19]1[n:20][cH:21][cH:22][s:23]1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH:9]([CH2:10][CH:11]2[CH2:12][CH2:13][CH2:14][CH2:15]2)[C:16](=[O:17])[NH:18][c:19]2[n:20][cH:21][cH:22][s:23]2)[cH:24][c:25]1[Br:26] | 0.49245 | CS(=O)(=O)c1ccc(C(CC2CCCC2)C(=O)O)cc1Br.ClCCl.Nc1nccs1.O=C1CCC(=O)N1Br.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>CS(=O)(=O)c1ccc(C(CC2CCCC2)C(=O)Nc2nccs2)cc1Br | CS(=O)(=O)c1ccc(C(CC2CCCC2)C(=O)O)cc1Br.ClCCl.Nc1nccs1.O=C1CCC(=O)N1Br.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>CS(=O)(=O)c1ccc(C(CC2CCCC2)C(=O)Nc2nccs2)cc1Br | US06320050B1_grants | 008b087aec76bc1694fde34c81b1acf48fb0c8e9c7fc3d584100c918 | ClCCl.O=C1CCC(=O)N1Br.O[C:16]([CH:9]([c:8]1[cH:7][cH:6][c:5]([S:2]([CH3:1])(=[O:3])=[O:4])[c:25]([Br:26])[cH:24]1)[CH2:10][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15]1)=[O:17].[NH2:18][c:19]1[n:20][cH:21][cH:22][s:23]1.c1ccc(P(c2ccccc2)c2ccccc2)cc1 | [CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH:9]([CH2:10][CH:11]2[CH2:12][CH2:13][CH2:14][CH2:15]2)[C:16](=[O:17])[NH:18][c:19]2[n:20][cH:21][cH:22][s:23]2)[cH:24][c:25]1[Br:26] | ([#16;a:4]:[c:5](:[#7;a:6])-[NH;D2;+0:7]-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3])>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([#16;a:4]:[c:5](:[#7;a:6])-[NH2;D1;+0:7]) | 1915f560d2e2ae3d3a4749f874a47ece1ab8982b05cac2f711ea52be | 1 | 1 | ClCCl.O=C1CCC(=O)N1Br.c1ccc(P(c2ccccc2)c2ccccc2)cc1 | 681 |
199,409 | 681,221 | 1,123,874 | C(OC(=O)[NH:7][C@@H:8]([CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)[C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16]1[CH:21]=[CH:20][N:19]=[C:18]([N:22]2[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[N:24]=[CH:23]2)[CH:17]=1)=[O:10])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][C@@H:8]([CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)[C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16]1[CH:21]=[CH:20][N:19]=[C:18]([N:22]2[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[N:24]=[CH:23]2)[CH:17]=1)=[O:10] | null | US08044209B2_0203 | 2,011 | CC(C)(C)OC(=O)[NH:1][C@H:2]([C:3](=[O:4])[N:5]1[CH2:6][CH2:7][CH2:8][C@H:9]1[c:10]1[cH:11][cH:12][n:13][c:14](-[n:15]2[cH:16][n:17][c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]23)[cH:24]1)[CH:25]1[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]1.ClCCl.O=C(O)C(F)(F)F>>[NH2:1][C@H:2]([C:3](=[O:4])[N:5]1[CH2:6][CH2:7][CH2:8][C@H:9]1[c:10]1[cH:11][cH:12][n:13][c:14](-[n:15]2[cH:16][n:17][c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]23)[cH:24]1)[CH:25]1[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]1 | 0.905671 | CC(C)(C)OC(=O)N[C@H](C(=O)N1CCC[C@H]1c1ccnc(-n2cnc3ccccc32)c1)C1CCCCC1.ClCCl.O=C(O)C(F)(F)F>>N[C@H](C(=O)N1CCC[C@H]1c1ccnc(-n2cnc3ccccc32)c1)C1CCCCC1 | CC(C)(C)OC(=O)N[C@H](C(=O)N1CCC[C@H]1c1ccnc(-n2cnc3ccccc32)c1)C1CCCCC1.ClCCl.O=C(O)C(F)(F)F>>N[C@H](C(=O)N1CCC[C@H]1c1ccnc(-n2cnc3ccccc32)c1)C1CCCCC1 | US08044209B2_0203grants | aadfacd1097a1b8a0def95e211c9ceb748ce705aea67a70db1f4bdde | CC(C)(C)OC(=O)[NH:1][C@H:2]([C:3](=[O:4])[N:5]1[CH2:6][CH2:7][CH2:8][C@H:9]1[c:10]1[cH:11][cH:12][n:13][c:14](-[n:15]2[cH:16][n:17][c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]23)[cH:24]1)[CH:25]1[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]1.ClCCl.O=C(O)C(F)(F)F | [NH2:1][C@H:2]([C:3](=[O:4])[N:5]1[CH2:6][CH2:7][CH2:8][C@H:9]1[c:10]1[cH:11][cH:12][n:13][c:14](-[n:15]2[cH:16][n:17][c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]23)[cH:24]1)[CH:25]1[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]1 | ([#7:4]-[C:3](=[O;D1;H0:5])-[C:2]-[NH2;D1;+0:1])>>(C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3](-[#7:4])=[O;D1;H0:5]) | 140717369b6c661d32f428907ffcecf2a0f3702c28cc263bfa3ac1c3 | 1 | 1 | ClCCl.O=C(O)C(F)(F)F | 431 |
132,860 | 483,808 | 815,164 | [OH:1][C:2]1[C:3]([CH3:12])=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH3:18]O>>[CH3:18][O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][C:10]([OH:11])=[C:2]([OH:1])[C:3]=1[CH3:12] | null | US07304161B2_0337 | 2,007 | O=S(=O)(O)O.O[C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[c:10]([OH:11])[c:12]1[CH3:13].[CH3:1][OH:2]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[c:10]([OH:11])[c:12]1[CH3:13] | 0.8548 | CO.Cc1c(C(=O)O)ccc(O)c1O.O=S(=O)(O)O>>COC(=O)c1ccc(O)c(O)c1C | CO.Cc1c(C(=O)O)ccc(O)c1O.O=S(=O)(O)O>>COC(=O)c1ccc(O)c(O)c1C | US07304161B2_0337grants | b8ab0d5becfd879373270375244868ca25d2404ee9df0c99e64c621f | O=S(=O)(O)O.O[C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[c:10]([OH:11])[c:12]1[CH3:13].[CH3:1][OH:2] | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[c:10]([OH:11])[c:12]1[CH3:13] | ([C;D1;H3:4]-[O;H0;D2;+0:5]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]).([C;D1;H3:4]-[OH;D1;+0:5]) | 462ff262701550e8361ae350b730fe337624136bbbc825e08432a1b4 | 1 | 1 | O=S(=O)(O)O | 33 |
88,346 | 350,081 | 596,635 | [CH3:1][CH:2]([CH2:4][CH:5]([OH:10])[CH2:6][CH:7]([CH3:9])[CH3:8])[CH3:3].C(N(CC)CC)C.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>C(Cl)(Cl)Cl>[CH3:18][S:19]([O:10][CH:5]([CH2:6][CH:7]([CH3:9])[CH3:8])[CH2:4][CH:2]([CH3:3])[CH3:1])(=[O:21])=[O:20] | null | US06531613B1_ | 2,003 | CCN(CC)CC.ClC(Cl)Cl.Cl[S:11]([CH3:12])(=[O:13])=[O:14].[CH3:1][CH:2]([CH3:3])[CH2:4][CH:5]([CH2:6][CH:7]([CH3:8])[CH3:9])[OH:10]>>[CH3:1][CH:2]([CH3:3])[CH2:4][CH:5]([CH2:6][CH:7]([CH3:8])[CH3:9])[O:10][S:11]([CH3:12])(=[O:13])=[O:14] | 0.33322 | CC(C)CC(O)CC(C)C.CCN(CC)CC.CS(=O)(=O)Cl.ClC(Cl)Cl>>CC(C)CC(CC(C)C)OS(C)(=O)=O | CC(C)CC(O)CC(C)C.CCN(CC)CC.CS(=O)(=O)Cl.ClC(Cl)Cl>>CC(C)CC(CC(C)C)OS(C)(=O)=O | US06531613B1_grants | ad9fccf12169846693f4342a106f392f1ee0b0237395878433efac06 | CCN(CC)CC.ClC(Cl)Cl.Cl[S:11]([CH3:12])(=[O:13])=[O:14].[CH3:1][CH:2]([CH3:3])[CH2:4][CH:5]([CH2:6][CH:7]([CH3:8])[CH3:9])[OH:10] | [CH3:1][CH:2]([CH3:3])[CH2:4][CH:5]([CH2:6][CH:7]([CH3:8])[CH3:9])[O:10][S:11]([CH3:12])(=[O:13])=[O:14] | ([C:5]-[O;H0;D2;+0:6]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4])>>(Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4]).([C:5]-[OH;D1;+0:6]) | 5b2ff2a69fb7bd6a032938e468684773bcc668928b037bbec0ac8335 | 1 | 1 | CCN(CC)CC.ClC(Cl)Cl | 0 |
120,488 | 447,067 | 759,508 | [Br:1][C:2]1[N:3]([CH2:19][CH2:20][CH2:21][C:22](OCC)=[O:23])[C:4]2[C:9]([C:10]=1[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.[H-].C([Al+]CC(C)C)C(C)C>C1COCC1>[Br:1][C:2]1[N:3]([CH2:19][CH2:20][CH2:21][CH:22]=[O:23])[C:4]2[C:9]([C:10]=1[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2 | |f:1.2| | US07144913B2_0205 | 2,006 | C1CCOC1.CC(C)C[Al+]CC(C)C.CCO[C:2](=[O:1])[CH2:3][CH2:4][CH2:5][n:6]1[c:7]([Br:8])[c:9]([CH2:10][c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]2)[c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]12.[H-]>>[O:1]=[CH:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]([Br:8])[c:9]([CH2:10][c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]2)[c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]12 | 0.915423 | C1CCOC1.CC(C)C[Al+]CC(C)C~[H-].CCOC(=O)CCCn1c(Br)c(Cc2ccc(Cl)cc2)c2ccccc21>>O=CCCCn1c(Br)c(Cc2ccc(Cl)cc2)c2ccccc21 | C1CCOC1.CC(C)C[Al+]CC(C)C.CCOC(=O)CCCn1c(Br)c(Cc2ccc(Cl)cc2)c2ccccc21.[H-]>>O=CCCCn1c(Br)c(Cc2ccc(Cl)cc2)c2ccccc21 | US07144913B2_0205grants | 2295b2265270d0b4ce78bf49e7f1d4dcaccde95900ef8a8ee2743490 | C1CCOC1.CC(C)C[Al+]CC(C)C.CCO[C:2](=[O:1])[CH2:3][CH2:4][CH2:5][n:6]1[c:7]([Br:8])[c:9]([CH2:10][c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]2)[c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]12.[H-] | [O:1]=[CH:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]([Br:8])[c:9]([CH2:10][c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]2)[c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]12 | ([C:2]-[CH;D2;+0:1]=[O;D1;H0:3])>>(C-C-O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]) | db85b5949311da6368bd183ce09ed8a1c0b4533cd92b970180aeab84 | 1 | 1 | C1CCOC1.CC(C)C[Al+]CC(C)C.[H-] | 260 |
131,465 | 479,644 | 809,238 | Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[Si:10]([O:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]>>[Si:10]([O:17][C:18]1[CH:19]=[CH:20][C:21]([C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)=[CH:22][CH:23]=1)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11] | null | US07279600B2_0086 | 2,007 | Br[c:13]1[cH:14][cH:15][c:16]([CH:17]=[O:18])[cH:19][cH:20]1.OB(O)[c:12]1[cH:11][cH:10][c:9]([O:8][Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7])[cH:22][cH:21]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][c:9]1[cH:10][cH:11][c:12](-[c:13]2[cH:14][cH:15][c:16]([CH:17]=[O:18])[cH:19][cH:20]2)[cH:21][cH:22]1 | 0.338178 | CC(C)(C)[Si](C)(C)Oc1ccc(B(O)O)cc1.O=Cc1ccc(Br)cc1>>CC(C)(C)[Si](C)(C)Oc1ccc(-c2ccc(C=O)cc2)cc1 | CC(C)(C)[Si](C)(C)Oc1ccc(B(O)O)cc1.O=Cc1ccc(Br)cc1>>CC(C)(C)[Si](C)(C)Oc1ccc(-c2ccc(C=O)cc2)cc1 | US07279600B2_0086grants | 48384fe4ca93e291f8d13785657e01e436a5d177c3d228dfcdb87b22 | Br[c:13]1[cH:14][cH:15][c:16]([CH:17]=[O:18])[cH:19][cH:20]1.OB(O)[c:12]1[cH:11][cH:10][c:9]([O:8][Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7])[cH:22][cH:21]1 | [CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][c:9]1[cH:10][cH:11][c:12](-[c:13]2[cH:14][cH:15][c:16]([CH:17]=[O:18])[cH:19][cH:20]2)[cH:21][cH:22]1 | ([c:5]:[c;H0;D3;+0:4](:[c:6])-[c;H0;D3;+0:1](:[c:2]):[c:3])>>(Br-[c;H0;D3;+0:1](:[c:2]):[c:3]).(O-B(-O)-[c;H0;D3;+0:4](:[c:5]):[c:6]) | 55251936defc26e51bebc585e4f1cda158e89f53686fa5d9c09591aa | 0.5 | 2 | null | 837 |
289,739 | 944,060 | 1,584,570 | [C:1]([C:5]1[CH:6]=[C:7]([CH:23]=[O:24])[C:8]([OH:22])=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18](F)(F)F)=[CH:13][CH:12]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].Br[C:26]1[C:27](O)=[C:28](C=[C:32](C(C)(C)C)[CH:33]=1)C=O.O(C1C=CC(B(O)O)=CC=1)C1C=CC=CC=1>>[C:1]([C:5]1[CH:6]=[C:7]([CH:23]=[O:24])[C:8]([OH:22])=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]3[CH:28]=[CH:27][CH:26]=[CH:33][CH:32]=3)=[CH:13][CH:12]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2] | null | US08962657B2_0226 | 2,015 | Br[c:12]1[c:10]([OH:11])[c:7]([CH:8]=[O:9])[cH:6][c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[cH:26]1.CC(C)(C)c1cc(C=O)c(O)c(-c2ccc(OC(F)(F)F)cc2)c1.OB(O)[c:13]1[cH:14][cH:15][c:16]([O:17][c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[cH:24][cH:25]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([CH:8]=[O:9])[c:10]([OH:11])[c:12](-[c:13]2[cH:14][cH:15][c:16]([O:17][c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)[cH:24][cH:25]2)[cH:26]1 | 0.136115 | CC(C)(C)c1cc(Br)c(O)c(C=O)c1.CC(C)(C)c1cc(C=O)c(O)c(-c2ccc(OC(F)(F)F)cc2)c1.OB(O)c1ccc(Oc2ccccc2)cc1>>CC(C)(C)c1cc(C=O)c(O)c(-c2ccc(Oc3ccccc3)cc2)c1 | CC(C)(C)c1cc(Br)c(O)c(C=O)c1.CC(C)(C)c1cc(C=O)c(O)c(-c2ccc(OC(F)(F)F)cc2)c1.OB(O)c1ccc(Oc2ccccc2)cc1>>CC(C)(C)c1cc(C=O)c(O)c(-c2ccc(Oc3ccccc3)cc2)c1 | US08962657B2_0226grants | 78be830e8f0713be972bf59ea8fd2a591b4e0a7368fc08c0299033e2 | Br[c:12]1[c:10]([OH:11])[c:7]([CH:8]=[O:9])[cH:6][c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[cH:26]1.CC(C)(C)c1cc(C=O)c(O)c(-c2ccc(OC(F)(F)F)cc2)c1.OB(O)[c:13]1[cH:14][cH:15][c:16]([O:17][c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[cH:24][cH:25]1 | [CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([CH:8]=[O:9])[c:10]([OH:11])[c:12](-[c:13]2[cH:14][cH:15][c:16]([O:17][c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)[cH:24][cH:25]2)[cH:26]1 | ([c:2]:[c;H0;D3;+0:1](:[c:3])-[c;H0;D3;+0:4](:[c:5]):[c:6])>>(Br-[c;H0;D3;+0:1](:[c:2]):[c:3]).(O-B(-O)-[c;H0;D3;+0:4](:[c:5]):[c:6]) | 55251936defc26e51bebc585e4f1cda158e89f53686fa5d9c09591aa | 0.5 | 2 | CC(C)(C)c1cc(C=O)c(O)c(-c2ccc(OC(F)(F)F)cc2)c1 | 837 |
374,530 | 837,180 | null | [Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[C:4]([C:13]([OH:15])=O)[CH:3]=1.[Cl:16][C:17]1[CH:23]=[C:22]([S:24]([C:27]([F:30])([F:29])[F:28])(=[O:26])=[O:25])[CH:21]=[CH:20][C:18]=1[NH2:19]>>[Cl:16][C:17]1[CH:23]=[C:22]([S:24]([C:27]([F:28])([F:29])[F:30])(=[O:26])=[O:25])[CH:21]=[CH:20][C:18]=1[NH:19][C:13]([C:4]1[CH:3]=[C:2]([Br:1])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]=1[OH:12])=[O:15] | null | US20100041657A1_0595 | 2,010 | O[C:2](=[O:1])[c:18]1[cH:19][c:20]([Br:21])[c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]2[c:28]1[OH:29].[NH2:3][c:4]1[cH:5][cH:6][c:7]([S:8](=[O:9])(=[O:10])[C:11]([F:12])([F:13])[F:14])[cH:15][c:16]1[Cl:17]>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([S:8](=[O:9])(=[O:10])[C:11]([F:12])([F:13])[F:14])[cH:15][c:16]1[Cl:17])[c:18]1[cH:19][c:20]([Br:21])[c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]2[c:28]1[OH:29] | 0.120405 | Nc1ccc(S(=O)(=O)C(F)(F)F)cc1Cl.O=C(O)c1cc(Br)c2ccccc2c1O>>O=C(Nc1ccc(S(=O)(=O)C(F)(F)F)cc1Cl)c1cc(Br)c2ccccc2c1O | Nc1ccc(S(=O)(=O)C(F)(F)F)cc1Cl.O=C(O)c1cc(Br)c2ccccc2c1O>>O=C(Nc1ccc(S(=O)(=O)C(F)(F)F)cc1Cl)c1cc(Br)c2ccccc2c1O | US20100041657A1_0595apps | c64968c51b8d1f1a5d7ea3d594b87500e4597505633b295cde3ce482 | O[C:2](=[O:1])[c:18]1[cH:19][c:20]([Br:21])[c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]2[c:28]1[OH:29].[NH2:3][c:4]1[cH:5][cH:6][c:7]([S:8](=[O:9])(=[O:10])[C:11]([F:12])([F:13])[F:14])[cH:15][c:16]1[Cl:17] | [O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([S:8](=[O:9])(=[O:10])[C:11]([F:12])([F:13])[F:14])[cH:15][c:16]1[Cl:17])[c:18]1[cH:19][c:20]([Br:21])[c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]2[c:28]1[OH:29] | ([O;D1;H0:2]=[C;H0;D3;+0:1](-[c:3])-[NH;D2;+0:4]-[c:5])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]).([NH2;D1;+0:4]-[c:5]) | 35b8cb0d38b7801143c15d7c216f0b66c154f00ac243d1252d6d0e55 | 1 | 1 | null | 50 |
283,828 | 928,562 | 1,554,475 | [CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:9]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[N:10][C:11]3[C:16]([N:17]=2)=[CH:15][C:14]([C:18]([O:20]C)=[O:19])=[CH:13][CH:12]=3)[CH2:4][CH2:3]1.[OH-].[Na+]>C1COCC1.CO.O>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:8]2[C:9]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[N:10][C:11]3[C:16]([N:17]=2)=[CH:15][C:14]([C:18]([OH:20])=[O:19])=[CH:13][CH:12]=3)[CH2:6][CH2:7]1 | |f:1.2,3.4| | US08916560B2_0480 | 2,014 | C1CCOC1.CO.C[O:13][C:11]([c:10]1[cH:9][c:8]2[n:7][c:6]([N:5]3[CH2:4][CH2:3][N:2]([CH3:1])[CH2:26][CH2:25]3)[c:18](-[c:19]3[cH:20][cH:21][cH:22][cH:23][cH:24]3)[n:17][c:16]2[cH:15][cH:14]1)=[O:12].O.[Na+].[OH-]>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[n:7][c:8]3[cH:9][c:10]([C:11](=[O:12])[OH:13])[cH:14][cH:15][c:16]3[n:17][c:18]2-[c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[CH2:25][CH2:26]1 | 0.798281 | C1CCOC1~CO.COC(=O)c1ccc2nc(-c3ccccc3)c(N3CCN(C)CC3)nc2c1.O.[Na+]~[OH-]>>CN1CCN(c2nc3cc(C(=O)O)ccc3nc2-c2ccccc2)CC1 | C1CCOC1.CO.COC(=O)c1ccc2nc(-c3ccccc3)c(N3CCN(C)CC3)nc2c1.O.[Na+].[OH-]>>CN1CCN(c2nc3cc(C(=O)O)ccc3nc2-c2ccccc2)CC1 | US08916560B2_0480grants | a3b291b4fc52a795fa247a7919d6a625f946cbd41249519db963a5e5 | C1CCOC1.CO.C[O:13][C:11]([c:10]1[cH:9][c:8]2[n:7][c:6]([N:5]3[CH2:4][CH2:3][N:2]([CH3:1])[CH2:26][CH2:25]3)[c:18](-[c:19]3[cH:20][cH:21][cH:22][cH:23][cH:24]3)[n:17][c:16]2[cH:15][cH:14]1)=[O:12].O.[Na+].[OH-] | [CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[n:7][c:8]3[cH:9][c:10]([C:11](=[O:12])[OH:13])[cH:14][cH:15][c:16]3[n:17][c:18]2-[c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[CH2:25][CH2:26]1 | ([O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4]1:[c:5]:[c:6]:[c:7]:[c:8]:[c:9]:1)>>(C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[c:5]:[c:6]:[c:7]:[c:8]:[c:9]:1) | 48f3c58ed4b2eb976195200c79ebaafb36d7eb1c6248c7c6424a4457 | 1 | 1 | C1CCOC1.CO.O.[Na+].[OH-] | 247 |
299,193 | 974,426 | 1,641,045 | [F:1][C:2]1[CH:7]=[C:6](B2OC(C)(C)C(C)(C)O2)[CH:5]=[CH:4][C:3]=1[C:17]1[N:18]=[CH:19][C:20]([NH2:23])=[N:21][CH:22]=1.Br[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[Cl:31]>>[Cl:31][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[C:6]1[CH:5]=[CH:4][C:3]([C:17]2[N:18]=[CH:19][C:20]([NH2:23])=[N:21][CH:22]=2)=[C:2]([F:1])[CH:7]=1 | null | US09079866B2_1598 | 2,015 | Br[c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[Cl:16].CC1(C)OB([c:9]2[cH:8][cH:7][c:6](-[c:5]3[n:4][cH:3][c:2]([NH2:1])[n:21][cH:20]3)[c:18]([F:19])[cH:17]2)OC1(C)C>>[NH2:1][c:2]1[cH:3][n:4][c:5](-[c:6]2[cH:7][cH:8][c:9](-[c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[Cl:16])[cH:17][c:18]2[F:19])[cH:20][n:21]1 | 0.979282 | CC1(C)OB(c2ccc(-c3cnc(N)cn3)c(F)c2)OC1(C)C.Clc1ccccc1Br>>Nc1cnc(-c2ccc(-c3ccccc3Cl)cc2F)cn1 | CC1(C)OB(c2ccc(-c3cnc(N)cn3)c(F)c2)OC1(C)C.Clc1ccccc1Br>>Nc1cnc(-c2ccc(-c3ccccc3Cl)cc2F)cn1 | US09079866B2_1598grants | d488421c982658f8b26b71709a836b902199de9731452e2f6427d6e4 | Br[c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[Cl:16].CC1(C)OB([c:9]2[cH:8][cH:7][c:6](-[c:5]3[n:4][cH:3][c:2]([NH2:1])[n:21][cH:20]3)[c:18]([F:19])[cH:17]2)OC1(C)C | [NH2:1][c:2]1[cH:3][n:4][c:5](-[c:6]2[cH:7][cH:8][c:9](-[c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[Cl:16])[cH:17][c:18]2[F:19])[cH:20][n:21]1 | ([c:2]:[c;H0;D3;+0:1](:[c:3])-[c;H0;D3;+0:4](:[c:5]):[c:6])>>(Br-[c;H0;D3;+0:1](:[c:2]):[c:3]).(C-C1(-C)-O-B(-[c;H0;D3;+0:4](:[c:5]):[c:6])-O-C-1(-C)-C) | 9070cdd4fb6f1677ab91185ae4f4e0309f05412abddf79c11415d35f | 0.5 | 2 | null | 933 |
375,488 | 853,980 | null | [CH3:1][C:2]1[C:6]2[C:7](=[O:19])[N:8]([CH2:12][CH2:13][N:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)[CH2:9][CH2:10][CH2:11][C:5]=2[NH:4][C:3]=1[CH:20]=O.[F:22][C:23]1[CH:24]=[C:25]2[C:29](=[C:30]([NH:32][CH:33]=[O:34])[CH:31]=1)[NH:28][C:27](=[O:35])[CH2:26]2>>[F:22][C:23]1[CH:24]=[C:25]2[C:29](=[C:30]([NH:32][CH:33]=[O:34])[CH:31]=1)[NH:28][C:27](=[O:35])[C:26]2=[CH:20][C:3]1[NH:4][C:5]2[CH2:11][CH2:10][CH2:9][N:8]([CH2:12][CH2:13][N:14]3[CH2:15][CH2:16][CH2:17][CH2:18]3)[C:7](=[O:19])[C:6]=2[C:2]=1[CH3:1] | null | US20100075952A1_0326 | 2,010 | O=[CH:4][c:3]1[c:2]([CH3:1])[c:21]2[c:20]([nH:19]1)[CH2:34][CH2:33][CH2:32][N:24]([CH2:25][CH2:26][N:27]1[CH2:28][CH2:29][CH2:30][CH2:31]1)[C:22]2=[O:23].[CH2:5]1[C:6](=[O:7])[NH:8][c:9]2[c:10]([NH:11][CH:12]=[O:13])[cH:14][c:15]([F:16])[cH:17][c:18]21>>[CH3:1][c:2]1[c:3]([CH:4]=[C:5]2[C:6](=[O:7])[NH:8][c:9]3[c:10]([NH:11][CH:12]=[O:13])[cH:14][c:15]([F:16])[cH:17][c:18]32)[nH:19][c:20]2[c:21]1[C:22](=[O:23])[N:24]([CH2:25][CH2:26][N:27]1[CH2:28][CH2:29][CH2:30][CH2:31]1)[CH2:32][CH2:33][CH2:34]2 | 0.919764 | Cc1c(C=O)[nH]c2c1C(=O)N(CCN1CCCC1)CCC2.O=CNc1cc(F)cc2c1NC(=O)C2>>Cc1c(C=C2C(=O)Nc3c(NC=O)cc(F)cc32)[nH]c2c1C(=O)N(CCN1CCCC1)CCC2 | Cc1c(C=O)[nH]c2c1C(=O)N(CCN1CCCC1)CCC2.O=CNc1cc(F)cc2c1NC(=O)C2>>Cc1c(C=C2C(=O)Nc3c(NC=O)cc(F)cc32)[nH]c2c1C(=O)N(CCN1CCCC1)CCC2 | US20100075952A1_0326apps | 4ec437b6969285bbc143d4bca0a5f06751e36a9b854b55017db17233 | O=[CH:4][c:3]1[c:2]([CH3:1])[c:21]2[c:20]([nH:19]1)[CH2:34][CH2:33][CH2:32][N:24]([CH2:25][CH2:26][N:27]1[CH2:28][CH2:29][CH2:30][CH2:31]1)[C:22]2=[O:23].[CH2:5]1[C:6](=[O:7])[NH:8][c:9]2[c:10]([NH:11][CH:12]=[O:13])[cH:14][c:15]([F:16])[cH:17][c:18]21 | [CH3:1][c:2]1[c:3]([CH:4]=[C:5]2[C:6](=[O:7])[NH:8][c:9]3[c:10]([NH:11][CH:12]=[O:13])[cH:14][c:15]([F:16])[cH:17][c:18]32)[nH:19][c:20]2[c:21]1[C:22](=[O:23])[N:24]([CH2:25][CH2:26][N:27]1[CH2:28][CH2:29][CH2:30][CH2:31]1)[CH2:32][CH2:33][CH2:34]2 | ([#7:4]-[C:5](=[O;D1;H0:6])-[C;H0;D3;+0:7](-[c:8])=[CH;D2;+0:1]-[c:2]:[#7;a:3])>>(O=[CH;D2;+0:1]-[c:2]:[#7;a:3]).([#7:4]-[C:5](=[O;D1;H0:6])-[CH2;D2;+0:7]-[c:8]) | 7924cbf0da79d1713912e854ce0d084a37ce4e2f134b0ab1fff2a499 | 1 | 1 | null | 440 |