JP2016537384A5 - - Google Patents
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- JP2016537384A5 JP2016537384A5 JP2016533073A JP2016533073A JP2016537384A5 JP 2016537384 A5 JP2016537384 A5 JP 2016537384A5 JP 2016533073 A JP2016533073 A JP 2016533073A JP 2016533073 A JP2016533073 A JP 2016533073A JP 2016537384 A5 JP2016537384 A5 JP 2016537384A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- dimethyl
- chlorophenyl
- oxo
- dihydropyrrolo
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 82
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 50
- 150000001875 compounds Chemical class 0.000 claims description 36
- 150000003839 salts Chemical class 0.000 claims description 36
- -1 methoxy, cyano, methyl Chemical group 0.000 claims description 31
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 28
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 206010028980 Neoplasm Diseases 0.000 claims description 6
- 201000011510 cancer Diseases 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000004952 protein activity Effects 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 18
- HMXQIFUGFZEJEO-UHFFFAOYSA-N 1,2-dihydropyrrol-3-one Chemical compound O=C1CNC=C1 HMXQIFUGFZEJEO-UHFFFAOYSA-N 0.000 claims 4
- IWTFOFMTUOBLHG-UHFFFAOYSA-N 2-methoxypyridine Chemical compound COC1=CC=CC=N1 IWTFOFMTUOBLHG-UHFFFAOYSA-N 0.000 claims 2
- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 claims 1
- XPDXANVGYAEATN-MRXNPFEDSA-N (6R)-5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-6-(4-chlorophenyl)-1-methyl-6H-pyrrolo[3,4-b]pyrrol-4-one Chemical compound ClC1=CC(=CN(C1=O)C)N1[C@@H](C=2N(C=CC2C1=O)C)C1=CC=C(C=C1)Cl XPDXANVGYAEATN-MRXNPFEDSA-N 0.000 claims 1
- QLRYSHYUZMZZPY-OAQYLSRUSA-N (6R)-6-(4-chlorophenyl)-2-(2,4-dimethoxypyrimidin-5-yl)-5-(1,5-dimethyl-6-oxopyridin-3-yl)-1-methyl-6H-pyrrolo[3,4-b]pyrrol-4-one Chemical compound ClC1=CC=C(C=C1)[C@H]1N(C(C2=C1N(C(=C2)C=2C(=NC(=NC2)OC)OC)C)=O)C2=CN(C(C(=C2)C)=O)C QLRYSHYUZMZZPY-OAQYLSRUSA-N 0.000 claims 1
- UQMYMWRETIHSGQ-HSZRJFAPSA-N (6R)-6-(4-chlorophenyl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-2-(2-methoxypyridin-3-yl)-1-methyl-6H-pyrrolo[3,4-b]pyrrol-4-one Chemical compound ClC1=CC=C(C=C1)[C@H]1N(C(C2=C1N(C(=C2)C=2C(=NC=CC2)OC)C)=O)C=2C=C(C=1N(C2)C(=NN1)C)C UQMYMWRETIHSGQ-HSZRJFAPSA-N 0.000 claims 1
- SMYPWBHABVYAJK-QHCPKHFHSA-N (6S)-6-(4-chlorophenyl)-2-(3,6-dihydro-2H-pyran-4-yl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-1-methyl-6H-pyrrolo[3,4-b]pyrrol-4-one Chemical compound ClC1=CC=C(C=C1)[C@@H]1N(C(C2=C1N(C(=C2)C=2CCOCC2)C)=O)C=2C=C(C=1N(C2)C(=NN1)C)C SMYPWBHABVYAJK-QHCPKHFHSA-N 0.000 claims 1
- MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 claims 1
- NBJPFMDWXKYTQF-UHFFFAOYSA-N 1-(1-acetylazetidin-3-yl)-6-(4-chlorophenyl)-3-cyclopropyl-5-(3,7-dimethyltriazolo[4,5-b]pyridin-5-yl)-6H-pyrrolo[3,4-b]pyrrol-4-one Chemical compound C(C)(=O)N1CC(C1)N1C2=C(C(=C1)C1CC1)C(N(C2C2=CC=C(C=C2)Cl)C2=CC(=C1C(=N2)N(N=N1)C)C)=O NBJPFMDWXKYTQF-UHFFFAOYSA-N 0.000 claims 1
- CASINEGODQBEAL-UHFFFAOYSA-N 1-(1-acetylazetidin-3-yl)-6-(4-chlorophenyl)-3-cyclopropyl-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-6H-pyrrolo[3,4-b]pyrrol-4-one Chemical compound C(C)(=O)N1CC(C1)N1C2=C(C(=C1)C1CC1)C(N(C2C2=CC=C(C=C2)Cl)C=2C=C(C=1N(C2)C(=NN1)C)C)=O CASINEGODQBEAL-UHFFFAOYSA-N 0.000 claims 1
- SVEGTFMYOXJKMY-UHFFFAOYSA-N 1-(1-acetylazetidin-3-yl)-6-(4-chlorophenyl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-methyl-6H-pyrrolo[3,4-b]pyrrol-4-one Chemical compound C(C)(=O)N1CC(C1)N1C2=C(C(=C1)C)C(N(C2C2=CC=C(C=C2)Cl)C=2C=C(C=1N(C2)C(=NN1)C)C)=O SVEGTFMYOXJKMY-UHFFFAOYSA-N 0.000 claims 1
- UWLHKAZBBAIBEB-UHFFFAOYSA-N 1-(azetidin-3-yl)-6-(4-chlorophenyl)-3-cyclopropyl-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-6H-pyrrolo[3,4-b]pyrrol-4-one Chemical compound N1CC(C1)N1C2=C(C(=C1)C1CC1)C(N(C2C2=CC=C(C=C2)Cl)C=2C=C(C=1N(C2)C(=NN1)C)C)=O UWLHKAZBBAIBEB-UHFFFAOYSA-N 0.000 claims 1
- IBKWVBBVOCBYKT-UHFFFAOYSA-N 1-(azetidin-3-yl)-6-(4-chlorophenyl)-5-(3,7-dimethyltriazolo[4,5-b]pyridin-5-yl)-3-methyl-6H-pyrrolo[3,4-b]pyrrol-4-one Chemical compound N1CC(C1)N1C2=C(C(=C1)C)C(N(C2C2=CC=C(C=C2)Cl)C2=CC(=C1C(=N2)N(N=N1)C)C)=O IBKWVBBVOCBYKT-UHFFFAOYSA-N 0.000 claims 1
- PQGBLUWWHXVVKD-UHFFFAOYSA-N 1-(azetidin-3-yl)-6-(4-chlorophenyl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-methyl-6H-pyrrolo[3,4-b]pyrrol-4-one Chemical compound N1CC(C1)N1C2=C(C(=C1)C)C(N(C2C2=CC=C(C=C2)Cl)C=2C=C(C=1N(C2)C(=NN1)C)C)=O PQGBLUWWHXVVKD-UHFFFAOYSA-N 0.000 claims 1
- ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 claims 1
- ZDYWXTGNQATUAC-UHFFFAOYSA-N 1-[6-(4-chlorophenyl)-5-(3,7-dimethylbenzotriazol-5-yl)-1-methyl-4-oxo-6H-pyrrolo[3,4-b]pyrrol-3-yl]-3-methylurea Chemical compound ClC1=CC=C(C=C1)C1N(C(C2=C1N(C=C2NC(=O)NC)C)=O)C=2C=C(C1=C(N(N=N1)C)C2)C ZDYWXTGNQATUAC-UHFFFAOYSA-N 0.000 claims 1
- VDVJQFLGCFFFBP-UHFFFAOYSA-N 2,3-dihydropyrrole-1-carboxylic acid Chemical compound OC(=O)N1CCC=C1 VDVJQFLGCFFFBP-UHFFFAOYSA-N 0.000 claims 1
- OJGGGCDIKGWBSR-UHFFFAOYSA-N 2-[6-(4-chlorophenyl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-methyl-4-oxo-6H-pyrrolo[3,4-b]pyrrol-1-yl]-N,N-dimethylacetamide Chemical compound ClC1=CC=C(C=C1)C1N(C(C2=C1N(C=C2C)CC(=O)N(C)C)=O)C=2C=C(C=1N(C2)C(=NN1)C)C OJGGGCDIKGWBSR-UHFFFAOYSA-N 0.000 claims 1
- KGPRTZSROXHRIX-UHFFFAOYSA-N 2-[6-(4-chlorophenyl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-methyl-4-oxo-6H-pyrrolo[3,4-b]pyrrol-1-yl]-N-methylacetamide Chemical compound ClC1=CC=C(C=C1)C1N(C(C2=C1N(C=C2C)CC(=O)NC)=O)C=2C=C(C=1N(C2)C(=NN1)C)C KGPRTZSROXHRIX-UHFFFAOYSA-N 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- RJDVRXGILIWOCC-UHFFFAOYSA-N 3-(1-acetylazetidin-3-yl)-6-(4-chlorophenyl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-1-methyl-6H-pyrrolo[2,3-c]pyrrol-4-one Chemical compound C(C)(=O)N1CC(C1)C=1C2=C(N(C1)C)C(N(C2=O)C=2C=C(C=1N(C2)C(=NN1)C)C)C1=CC=C(C=C1)Cl RJDVRXGILIWOCC-UHFFFAOYSA-N 0.000 claims 1
- HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 claims 1
- CRYAUTCZOKUESS-UHFFFAOYSA-N 3-(azetidin-3-yl)-6-(4-chlorophenyl)-5-(3,7-dimethyltriazolo[4,5-b]pyridin-5-yl)-1-methyl-6H-pyrrolo[2,3-c]pyrrol-4-one Chemical compound N1CC(C1)C=1C2=C(N(C1)C)C(N(C2=O)C2=CC(=C1C(=N2)N(N=N1)C)C)C1=CC=C(C=C1)Cl CRYAUTCZOKUESS-UHFFFAOYSA-N 0.000 claims 1
- WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 claims 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- VBWJYWJSBHIBOW-UHFFFAOYSA-N 4-[5-(1,5-dimethyl-6-oxopyridin-3-yl)-1-methyl-4-oxo-6H-pyrrolo[3,4-b]pyrrol-6-yl]benzonitrile Chemical compound CN1C=C(C=C(C1=O)C)N1C(C=2N(C=CC2C1=O)C)C1=CC=C(C#N)C=C1 VBWJYWJSBHIBOW-UHFFFAOYSA-N 0.000 claims 1
- WGVAADOVZXANRM-UHFFFAOYSA-N 4-[5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-1-methyl-4-oxo-6H-pyrrolo[3,4-b]pyrrol-6-yl]benzonitrile Chemical compound ClC1=CC(=CN(C1=O)C)N1C(C=2N(C=CC2C1=O)C)C1=CC=C(C#N)C=C1 WGVAADOVZXANRM-UHFFFAOYSA-N 0.000 claims 1
- KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- NHUYOZGLCLQXEB-UHFFFAOYSA-N 5-(1,5-dimethyl-6-oxopyridin-3-yl)-1-methyl-6-(4-methylphenyl)-6H-pyrrolo[3,4-b]pyrrol-4-one Chemical compound CN1C=C(C=C(C1=O)C)N1C(C=2N(C=CC2C1=O)C)C1=CC=C(C=C1)C NHUYOZGLCLQXEB-UHFFFAOYSA-N 0.000 claims 1
- XITXIIWQQYIONX-UHFFFAOYSA-N 5-(1,5-dimethyl-6-oxopyridin-3-yl)-1-methyl-6-phenyl-6H-pyrrolo[3,4-b]pyrrol-4-one Chemical compound CN1C=C(C=C(C1=O)C)N1C(C=2N(C=CC2C1=O)C)C1=CC=CC=C1 XITXIIWQQYIONX-UHFFFAOYSA-N 0.000 claims 1
- MTKZUOYFXZHUDU-UHFFFAOYSA-N 5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-1-methyl-6-(4-methylphenyl)-6H-pyrrolo[3,4-b]pyrrol-4-one Chemical compound ClC1=CC(=CN(C1=O)C)N1C(C=2N(C=CC2C1=O)C)C1=CC=C(C=C1)C MTKZUOYFXZHUDU-UHFFFAOYSA-N 0.000 claims 1
- SCAMMXNLCDAQKQ-UHFFFAOYSA-N 5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-1-methyl-6-phenyl-6H-pyrrolo[3,4-b]pyrrol-4-one Chemical compound ClC1=CC(=CN(C1=O)C)N1C(C=2N(C=CC2C1=O)C)C1=CC=CC=C1 SCAMMXNLCDAQKQ-UHFFFAOYSA-N 0.000 claims 1
- ZQXOBYVSSHZKCM-UHFFFAOYSA-N 5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-6-(3-methoxyphenyl)-1-methyl-6H-pyrrolo[3,4-b]pyrrol-4-one Chemical compound ClC1=CC(=CN(C1=O)C)N1C(C=2N(C=CC2C1=O)C)C1=CC(=CC=C1)OC ZQXOBYVSSHZKCM-UHFFFAOYSA-N 0.000 claims 1
- ZBZCQXDDHPHITA-UHFFFAOYSA-N 5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-6-(4-chlorophenyl)-1,2-dimethyl-6H-pyrrolo[3,4-b]pyrrol-4-one Chemical compound ClC1=CC(=CN(C1=O)C)N1C(C=2N(C(=CC2C1=O)C)C)C1=CC=C(C=C1)Cl ZBZCQXDDHPHITA-UHFFFAOYSA-N 0.000 claims 1
- VAXZYGLGDOWBGT-UHFFFAOYSA-N 5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-6-(4-chlorophenyl)-1-cyclopropyl-2-(1-methyl-2-oxopyridin-3-yl)-6H-pyrrolo[3,4-b]pyrrol-4-one Chemical compound ClC1=CC(=CN(C1=O)C)N1C(C=2N(C(=CC2C1=O)C=1C(N(C=CC1)C)=O)C1CC1)C1=CC=C(C=C1)Cl VAXZYGLGDOWBGT-UHFFFAOYSA-N 0.000 claims 1
- UGVSWFJGRKHVMD-UHFFFAOYSA-N 5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-6-(4-chlorophenyl)-1-cyclopropyl-2-(1-methyl-6-oxopyridin-2-yl)-6H-pyrrolo[3,4-b]pyrrol-4-one Chemical compound ClC1=CC(=CN(C1=O)C)N1C(C=2N(C(=CC2C1=O)C=1N(C(C=CC1)=O)C)C1CC1)C1=CC=C(C=C1)Cl UGVSWFJGRKHVMD-UHFFFAOYSA-N 0.000 claims 1
- NYYPYDLZLGCKOU-UHFFFAOYSA-N 5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-6-(4-chlorophenyl)-1-cyclopropyl-2-(1-methyl-6-oxopyridin-3-yl)-6H-pyrrolo[3,4-b]pyrrol-4-one Chemical compound ClC1=CC(=CN(C1=O)C)N1C(C=2N(C(=CC2C1=O)C1=CN(C(C=C1)=O)C)C1CC1)C1=CC=C(C=C1)Cl NYYPYDLZLGCKOU-UHFFFAOYSA-N 0.000 claims 1
- XPDXANVGYAEATN-UHFFFAOYSA-N 5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-6-(4-chlorophenyl)-1-methyl-6H-pyrrolo[3,4-b]pyrrol-4-one Chemical compound ClC1=CC(=CN(C1=O)C)N1C(C=2N(C=CC2C1=O)C)C1=CC=C(C=C1)Cl XPDXANVGYAEATN-UHFFFAOYSA-N 0.000 claims 1
- IJUSAWCETGWNEQ-UHFFFAOYSA-N 5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-6-(4-chlorophenyl)-2-(2-methoxypyrimidin-4-yl)-1-methyl-6H-pyrrolo[3,4-b]pyrrol-4-one Chemical compound ClC1=CC(=CN(C1=O)C)N1C(C=2N(C(=CC2C1=O)C1=NC(=NC=C1)OC)C)C1=CC=C(C=C1)Cl IJUSAWCETGWNEQ-UHFFFAOYSA-N 0.000 claims 1
- WQRKDXUDKMFKPL-UHFFFAOYSA-N 5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-6-(4-chlorophenyl)-2-(2-methoxypyrimidin-5-yl)-1-methyl-6H-pyrrolo[3,4-b]pyrrol-4-one Chemical compound ClC1=CC(=CN(C1=O)C)N1C(C=2N(C(=CC2C1=O)C=1C=NC(=NC1)OC)C)C1=CC=C(C=C1)Cl WQRKDXUDKMFKPL-UHFFFAOYSA-N 0.000 claims 1
- IXWMDWQZYYSEGS-UHFFFAOYSA-N 5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-6-(4-fluorophenyl)-1-methyl-6H-pyrrolo[3,4-b]pyrrol-4-one Chemical compound ClC1=CC(=CN(C1=O)C)N1C(C=2N(C=CC2C1=O)C)C1=CC=C(C=C1)F IXWMDWQZYYSEGS-UHFFFAOYSA-N 0.000 claims 1
- LBELIXDRRWMQKV-UHFFFAOYSA-N 5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-6-(4-methoxyphenyl)-1-methyl-6H-pyrrolo[3,4-b]pyrrol-4-one Chemical compound ClC1=CC(=CN(C1=O)C)N1C(C=2N(C=CC2C1=O)C)C1=CC=C(C=C1)OC LBELIXDRRWMQKV-UHFFFAOYSA-N 0.000 claims 1
- DTIQMIRHDCHPIP-UHFFFAOYSA-N 6-(4-chloro-3-fluorophenyl)-5-(1,5-dimethyl-6-oxopyridin-3-yl)-1-methyl-6H-pyrrolo[3,4-b]pyrrol-4-one Chemical compound ClC1=C(C=C(C=C1)C1N(C(C2=C1N(C=C2)C)=O)C2=CN(C(C(=C2)C)=O)C)F DTIQMIRHDCHPIP-UHFFFAOYSA-N 0.000 claims 1
- AWTFSKPTZUHXSW-UHFFFAOYSA-N 6-(4-chloro-3-fluorophenyl)-5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-1-methyl-6H-pyrrolo[3,4-b]pyrrol-4-one Chemical compound ClC1=CC(=CN(C1=O)C)N1C(C=2N(C=CC2C1=O)C)C1=CC(=C(C=C1)Cl)F AWTFSKPTZUHXSW-UHFFFAOYSA-N 0.000 claims 1
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- MJTVRIBROYBHIV-UHFFFAOYSA-N 6-(4-chlorophenyl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-2-(2-oxo-1H-pyridin-3-yl)-1,6-dihydropyrrolo[3,4-b]pyrrol-4-one Chemical compound ClC1=CC=C(C=C1)C1N(C(C2=C1NC(=C2)C=2C(=NC=CC2)O)=O)C=2C=C(C=1N(C2)C(=NN1)C)C MJTVRIBROYBHIV-UHFFFAOYSA-N 0.000 claims 1
- JMENTVKUBOUMCJ-UHFFFAOYSA-N 6-(4-chlorophenyl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-methyl-1,6-dihydropyrrolo[3,4-b]pyrrol-4-one Chemical compound ClC1=CC=C(C=C1)C1N(C(C2=C1NC=C2C)=O)C=2C=C(C=1N(C2)C(=NN1)C)C JMENTVKUBOUMCJ-UHFFFAOYSA-N 0.000 claims 1
- WEWCBQWPGVKVPY-UHFFFAOYSA-N 6-(4-chlorophenyl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-methyl-1-(1-methyl-2-oxopyrrolidin-3-yl)-6H-pyrrolo[3,4-b]pyrrol-4-one Chemical compound ClC1=CC=C(C=C1)C1N(C(C2=C1N(C=C2C)C2C(N(CC2)C)=O)=O)C=2C=C(C=1N(C2)C(=NN1)C)C WEWCBQWPGVKVPY-UHFFFAOYSA-N 0.000 claims 1
- DVICYEUYFBDIJO-UHFFFAOYSA-N 6-(4-chlorophenyl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-methyl-1-(1-methylazetidin-3-yl)-6H-pyrrolo[3,4-b]pyrrol-4-one Chemical compound ClC1=CC=C(C=C1)C1N(C(C2=C1N(C=C2C)C2CN(C2)C)=O)C=2C=C(C=1N(C2)C(=NN1)C)C DVICYEUYFBDIJO-UHFFFAOYSA-N 0.000 claims 1
- PKHUSSXCMLLVRI-UHFFFAOYSA-N 6-(4-chlorophenyl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-methyl-1-(oxetan-3-yl)-6H-pyrrolo[3,4-b]pyrrol-4-one Chemical compound ClC1=CC=C(C=C1)C1N(C(C2=C1N(C=C2C)C2COC2)=O)C=2C=C(C=1N(C2)C(=NN1)C)C PKHUSSXCMLLVRI-UHFFFAOYSA-N 0.000 claims 1
- TUXHCXODKHDHKT-UHFFFAOYSA-N 6-(4-chlorophenyl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-N,1-dimethyl-4-oxo-6H-pyrrolo[3,4-b]pyrrole-3-carboxamide Chemical compound ClC1=CC=C(C=C1)C1N(C(C2=C1N(C=C2C(=O)NC)C)=O)C=2C=C(C=1N(C2)C(=NN1)C)C TUXHCXODKHDHKT-UHFFFAOYSA-N 0.000 claims 1
- NRKGWEXMFVBBBE-UHFFFAOYSA-N 6-(4-chlorophenyl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-N,3-dimethyl-4-oxo-6H-pyrrolo[3,4-b]pyrrole-1-carboxamide Chemical compound ClC1=CC=C(C=C1)C1N(C(C2=C1N(C=C2C)C(=O)NC)=O)C=2C=C(C=1N(C2)C(=NN1)C)C NRKGWEXMFVBBBE-UHFFFAOYSA-N 0.000 claims 1
- JKTAXQJDSRMHSS-UHFFFAOYSA-N 6-(4-chlorophenyl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-N,N,1-trimethyl-4-oxo-6H-pyrrolo[3,4-b]pyrrole-3-carboxamide Chemical compound ClC1=CC=C(C=C1)C1N(C(C2=C1N(C=C2C(=O)N(C)C)C)=O)C=2C=C(C=1N(C2)C(=NN1)C)C JKTAXQJDSRMHSS-UHFFFAOYSA-N 0.000 claims 1
- QXTHZAMLLIIJHM-UHFFFAOYSA-N 6-(4-chlorophenyl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-N,N,3-trimethyl-4-oxo-6H-pyrrolo[3,4-b]pyrrole-1-carboxamide Chemical compound ClC1=CC=C(C=C1)C1N(C(C2=C1N(C=C2C)C(=O)N(C)C)=O)C=2C=C(C=1N(C2)C(=NN1)C)C QXTHZAMLLIIJHM-UHFFFAOYSA-N 0.000 claims 1
- IITSESCLMNYTBQ-UHFFFAOYSA-N 6-(4-chlorophenyl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-N,N-dimethyl-4-oxo-6H-pyrrolo[3,4-b]pyrrole-1-carboxamide Chemical compound ClC1=CC=C(C=C1)C1N(C(C2=C1N(C=C2)C(=O)N(C)C)=O)C=2C=C(C=1N(C2)C(=NN1)C)C IITSESCLMNYTBQ-UHFFFAOYSA-N 0.000 claims 1
- BTGFLXGQPNRXDH-UHFFFAOYSA-N 6-(4-chlorophenyl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-N-methyl-4-oxo-6H-pyrrolo[3,4-b]pyrrole-1-carboxamide Chemical compound ClC1=CC=C(C=C1)C1N(C(C2=C1N(C=C2)C(=O)NC)=O)C=2C=C(C=1N(C2)C(=NN1)C)C BTGFLXGQPNRXDH-UHFFFAOYSA-N 0.000 claims 1
- CURNKPOFSHNCQW-UHFFFAOYSA-N 6-(4-chlorophenyl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-1-methyl-6H-pyrrolo[3,4-b]pyrrol-4-one Chemical compound ClC1=CC=C(C=C1)C1N(C(C2=C1N(C=C2)C)=O)C=2C=C(C=1N(N2)C(=NN1)C)C CURNKPOFSHNCQW-UHFFFAOYSA-N 0.000 claims 1
- IAYAEBUJIVBSPF-UHFFFAOYSA-N 6-(4-chlorophenyl)-5-[3-(difluoromethyl)-8-methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl]-1,3-dimethyl-6H-pyrrolo[3,4-b]pyrrol-4-one Chemical compound ClC1=CC=C(C=C1)C1N(C(C2=C1N(C=C2C)C)=O)C=2C=C(C=1N(C2)C(=NN1)C(F)F)C IAYAEBUJIVBSPF-UHFFFAOYSA-N 0.000 claims 1
- LDQWWSKUZGJSPQ-UHFFFAOYSA-N 6-(4-chlorophenyl)-5-[3-(difluoromethyl)-8-methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl]-N,1-dimethyl-4-oxo-6H-pyrrolo[3,4-b]pyrrole-3-carboxamide Chemical compound ClC1=CC=C(C=C1)C1N(C(C2=C1N(C=C2C(=O)NC)C)=O)C=2C=C(C=1N(C2)C(=NN1)C(F)F)C LDQWWSKUZGJSPQ-UHFFFAOYSA-N 0.000 claims 1
- CYZNNGBIFDNKBV-UHFFFAOYSA-N 6-(4-chlorophenyl)-5-[3-(difluoromethyl)-8-methyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]-N,1-dimethyl-4-oxo-6H-pyrrolo[3,4-b]pyrrole-3-carboxamide Chemical compound ClC1=CC=C(C=C1)C1N(C(C2=C1N(C=C2C(=O)NC)C)=O)C=2C=C(C=1N(N2)C(=NN1)C(F)F)C CYZNNGBIFDNKBV-UHFFFAOYSA-N 0.000 claims 1
- WSQOJBUQSYKMGG-UHFFFAOYSA-N 6-(4-chlorophenyl)-N-[2-(dimethylamino)ethyl]-5-(3,7-dimethylbenzotriazol-5-yl)-1-methyl-4-oxo-6H-pyrrolo[3,4-b]pyrrole-3-carboxamide Chemical compound ClC1=CC=C(C=C1)C1N(C(C2=C1N(C=C2C(=O)NCCN(C)C)C)=O)C=2C=C(C1=C(N(N=N1)C)C2)C WSQOJBUQSYKMGG-UHFFFAOYSA-N 0.000 claims 1
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims 1
- CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 claims 1
- AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 claims 1
- SSELZXGQLGXCDT-HXUWFJFHSA-N N-[(6R)-6-(4-chlorophenyl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-1-methyl-4-oxo-6H-pyrrolo[3,4-b]pyrrol-3-yl]acetamide Chemical compound ClC1=CC=C(C=C1)[C@H]1N(C(C2=C1N(C=C2NC(C)=O)C)=O)C=2C=C(C=1N(C2)C(=NN1)C)C SSELZXGQLGXCDT-HXUWFJFHSA-N 0.000 claims 1
- KGAKOIGDOIZZOQ-UHFFFAOYSA-N N-[6-(4-chlorophenyl)-5-(3,7-dimethylbenzotriazol-5-yl)-1-methyl-4-oxo-6H-pyrrolo[3,4-b]pyrrol-3-yl]-3-(dimethylamino)propanamide Chemical compound ClC1=CC=C(C=C1)C1N(C(C2=C1N(C=C2NC(CCN(C)C)=O)C)=O)C=2C=C(C1=C(N(N=N1)C)C2)C KGAKOIGDOIZZOQ-UHFFFAOYSA-N 0.000 claims 1
- LZQJKADDYCLNSB-UHFFFAOYSA-N N-[6-(4-chlorophenyl)-5-(3,7-dimethylbenzotriazol-5-yl)-1-methyl-4-oxo-6H-pyrrolo[3,4-b]pyrrol-3-yl]acetamide Chemical compound ClC1=CC=C(C=C1)C1N(C(C2=C1N(C=C2NC(C)=O)C)=O)C=2C=C(C1=C(N(N=N1)C)C2)C LZQJKADDYCLNSB-UHFFFAOYSA-N 0.000 claims 1
- DGXUFGAFFVEFEU-UHFFFAOYSA-N N-[6-(4-chlorophenyl)-5-(3,7-dimethyltriazolo[4,5-b]pyridin-5-yl)-1-methyl-4-oxo-6H-pyrrolo[3,4-b]pyrrol-3-yl]acetamide Chemical compound ClC1=CC=C(C=C1)C1N(C(C2=C1N(C=C2NC(C)=O)C)=O)C2=CC(=C1C(=N2)N(N=N1)C)C DGXUFGAFFVEFEU-UHFFFAOYSA-N 0.000 claims 1
- CRXLFEZLSZPQMT-UHFFFAOYSA-N N-[6-(4-chlorophenyl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-1-methyl-4-oxo-6H-pyrrolo[3,4-b]pyrrol-3-yl]-2-(dimethylamino)acetamide Chemical compound ClC1=CC=C(C=C1)C1N(C(C2=C1N(C=C2NC(CN(C)C)=O)C)=O)C=2C=C(C=1N(C2)C(=NN1)C)C CRXLFEZLSZPQMT-UHFFFAOYSA-N 0.000 claims 1
- SSELZXGQLGXCDT-UHFFFAOYSA-N N-[6-(4-chlorophenyl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-1-methyl-4-oxo-6H-pyrrolo[3,4-b]pyrrol-3-yl]acetamide Chemical compound ClC1=CC=C(C=C1)C1N(C(C2=C1N(C=C2NC(C)=O)C)=O)C=2C=C(C=1N(C2)C(=NN1)C)C SSELZXGQLGXCDT-UHFFFAOYSA-N 0.000 claims 1
- FESHYOISGIZOBW-UHFFFAOYSA-N N-[6-(4-chlorophenyl)-5-[3-(difluoromethyl)-8-methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl]-1-methyl-4-oxo-6H-pyrrolo[3,4-b]pyrrol-3-yl]-2-(dimethylamino)acetamide Chemical compound ClC1=CC=C(C=C1)C1N(C(C2=C1N(C=C2NC(CN(C)C)=O)C)=O)C=2C=C(C=1N(C2)C(=NN1)C(F)F)C FESHYOISGIZOBW-UHFFFAOYSA-N 0.000 claims 1
- UCOMAESNVXJEIJ-UHFFFAOYSA-N N-[6-(4-chlorophenyl)-5-[3-(difluoromethyl)-8-methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl]-1-methyl-4-oxo-6H-pyrrolo[3,4-b]pyrrol-3-yl]acetamide Chemical compound ClC1=CC=C(C=C1)C1N(C(C2=C1N(C=C2NC(C)=O)C)=O)C=2C=C(C=1N(C2)C(=NN1)C(F)F)C UCOMAESNVXJEIJ-UHFFFAOYSA-N 0.000 claims 1
- XYESNEVBCXKVML-UHFFFAOYSA-N N-[6-(4-chlorophenyl)-5-[3-(difluoromethyl)-8-methyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]-1-methyl-4-oxo-6H-pyrrolo[3,4-b]pyrrol-3-yl]-3-(dimethylamino)propanamide Chemical compound ClC1=CC=C(C=C1)C1N(C(C2=C1N(C=C2NC(CCN(C)C)=O)C)=O)C=2C=C(C=1N(N2)C(=NN1)C(F)F)C XYESNEVBCXKVML-UHFFFAOYSA-N 0.000 claims 1
- KDVBPVJMVKBRPB-UHFFFAOYSA-N N-[6-(4-chlorophenyl)-5-[3-(difluoromethyl)-8-methyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]-1-methyl-4-oxo-6H-pyrrolo[3,4-b]pyrrol-3-yl]acetamide Chemical compound ClC1=CC=C(C=C1)C1N(C(C2=C1N(C=C2NC(C)=O)C)=O)C=2C=C(C=1N(N2)C(=NN1)C(F)F)C KDVBPVJMVKBRPB-UHFFFAOYSA-N 0.000 claims 1
- LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- WEHPZXXDBNJUIG-UHFFFAOYSA-N ethyl 3-[6-(4-chlorophenyl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-methyl-4-oxo-6H-pyrrolo[3,4-b]pyrrol-1-yl]azetidine-1-carboxylate Chemical compound ClC1=CC=C(C=C1)C1N(C(C2=C1N(C=C2C)C2CN(C2)C(=O)OCC)=O)C=2C=C(C=1N(C2)C(=NN1)C)C WEHPZXXDBNJUIG-UHFFFAOYSA-N 0.000 claims 1
- XQCLLKJYKDIUDW-UHFFFAOYSA-N ethyl 6-(4-chlorophenyl)-2-(3,6-dihydro-2H-pyran-4-yl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-methyl-4-oxo-6H-pyrrolo[3,4-b]pyrrole-1-carboxylate Chemical compound ClC1=CC=C(C=C1)C1N(C(C2=C1N(C(=C2C)C=2CCOCC2)C(=O)OCC)=O)C=2C=C(C=1N(C2)C(=NN1)C)C XQCLLKJYKDIUDW-UHFFFAOYSA-N 0.000 claims 1
- FZOWBAIZBAZQAF-UHFFFAOYSA-N ethyl 6-(4-chlorophenyl)-3-cyclopropyl-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-4-oxo-6H-pyrrolo[2,3-c]pyrrole-1-carboxylate Chemical compound ClC1=CC=C(C=C1)C1N(C(C2=C1N(C=C2C2CC2)C(=O)OCC)=O)C=2C=C(C=1N(C2)C(=NN1)C)C FZOWBAIZBAZQAF-UHFFFAOYSA-N 0.000 claims 1
- VBNIZIAZOQSIGW-UHFFFAOYSA-N ethyl 6-(4-chlorophenyl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-2-(2-methoxypyridin-3-yl)-3-methyl-4-oxo-6H-pyrrolo[3,4-b]pyrrole-1-carboxylate Chemical compound ClC1=CC=C(C=C1)C1N(C(C2=C1N(C(=C2C)C=2C(=NC=CC2)OC)C(=O)OCC)=O)C=2C=C(C=1N(C2)C(=NN1)C)C VBNIZIAZOQSIGW-UHFFFAOYSA-N 0.000 claims 1
- JVTTVFOTQZIFEV-UHFFFAOYSA-N ethyl 6-(4-chlorophenyl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-methyl-4-oxo-6H-pyrrolo[3,4-b]pyrrole-1-carboxylate Chemical compound ClC1=CC=C(C=C1)C1N(C(C2=C1N(C=C2C)C(=O)OCC)=O)C=2C=C(C=1N(C2)C(=NN1)C)C JVTTVFOTQZIFEV-UHFFFAOYSA-N 0.000 claims 1
- ZSHUBSUFZWWFGQ-UHFFFAOYSA-N ethyl N-[6-(4-chlorophenyl)-5-(3,7-dimethyltriazolo[4,5-b]pyridin-5-yl)-1-methyl-4-oxo-6H-pyrrolo[3,4-b]pyrrol-3-yl]carbamate Chemical compound ClC1=CC=C(C=C1)C1N(C(C2=C1N(C=C2NC(OCC)=O)C)=O)C2=CC(=C1C(=N2)N(N=N1)C)C ZSHUBSUFZWWFGQ-UHFFFAOYSA-N 0.000 claims 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 claims 1
- KDRSWORUPZEOGX-UHFFFAOYSA-N tert-butyl N-[6-(4-chlorophenyl)-5-(3,7-dimethyltriazolo[4,5-b]pyridin-5-yl)-1-methyl-4-oxo-6H-pyrrolo[3,4-b]pyrrol-3-yl]carbamate Chemical compound ClC1=CC=C(C=C1)C1N(C(C2=C1N(C=C2NC(OC(C)(C)C)=O)C)=O)C2=CC(=C1C(=N2)N(N=N1)C)C KDRSWORUPZEOGX-UHFFFAOYSA-N 0.000 claims 1
- QWMJOPLEXJAKPN-UHFFFAOYSA-N tert-butyl N-[6-(4-chlorophenyl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-1-methyl-4-oxo-6H-pyrrolo[3,4-b]pyrrol-3-yl]carbamate Chemical compound ClC1=CC=C(C=C1)C1N(C(C2=C1N(C=C2NC(OC(C)(C)C)=O)C)=O)C=2C=C(C=1N(C2)C(=NN1)C)C QWMJOPLEXJAKPN-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 description 3
- 239000013543 active substance Substances 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
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| JP2021008407A (ja) * | 2017-10-02 | 2021-01-28 | 武田薬品工業株式会社 | 複素環化合物 |
| JPWO2020189525A1 (cg-RX-API-DMAC7.html) * | 2019-03-15 | 2020-09-24 | ||
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2014
- 2014-11-20 EP EP14812645.1A patent/EP3071571A1/en not_active Withdrawn
- 2014-11-20 EA EA201691058A patent/EA029269B1/ru not_active IP Right Cessation
- 2014-11-20 JP JP2016533073A patent/JP2016537384A/ja active Pending
- 2014-11-20 WO PCT/IB2014/066199 patent/WO2015075665A1/en not_active Ceased
- 2014-11-20 CA CA2931249A patent/CA2931249A1/en not_active Abandoned
- 2014-11-20 AU AU2014351413A patent/AU2014351413B2/en not_active Ceased
- 2014-11-20 CN CN201480073531.1A patent/CN105916857B/zh not_active Expired - Fee Related
- 2014-11-20 MX MX2016006667A patent/MX2016006667A/es unknown
- 2014-11-20 KR KR1020167016075A patent/KR20160086930A/ko not_active Withdrawn
- 2014-11-20 US US15/037,116 patent/US9550796B2/en not_active Expired - Fee Related