JP2016520116A5 - - Google Patents
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- Publication number
- JP2016520116A5 JP2016520116A5 JP2016516276A JP2016516276A JP2016520116A5 JP 2016520116 A5 JP2016520116 A5 JP 2016520116A5 JP 2016516276 A JP2016516276 A JP 2016516276A JP 2016516276 A JP2016516276 A JP 2016516276A JP 2016520116 A5 JP2016520116 A5 JP 2016520116A5
- Authority
- JP
- Japan
- Prior art keywords
- imidazol
- chlorophenyl
- dihydropyrrolo
- dimethyl
- oxo
- 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.)
- Granted
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- 150000003839 salts Chemical class 0.000 claims 15
- 150000001875 compounds Chemical class 0.000 claims 14
- -1 cyano, methyl Chemical group 0.000 claims 11
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 claims 5
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 125000001475 halogen functional group Chemical group 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- XNRZMTWJFLFRMR-OAQYLSRUSA-N (6r)-6-(4-chlorophenyl)-5-(1,5-dimethyl-6-oxopyridin-3-yl)-2-(6-methoxypyridin-3-yl)-1,6-dihydropyrrolo[3,4-d]imidazol-4-one Chemical compound C1=NC(OC)=CC=C1C(N1)=NC2=C1[C@@H](C=1C=CC(Cl)=CC=1)N(C1=CN(C)C(=O)C(C)=C1)C2=O XNRZMTWJFLFRMR-OAQYLSRUSA-N 0.000 claims 1
- MZKIOOQWOZDDMX-OAQYLSRUSA-N (6r)-6-(4-chlorophenyl)-5-(1,5-dimethyl-6-oxopyridin-3-yl)-2-(6-methoxypyridin-3-yl)-3-methyl-6h-pyrrolo[3,4-d]imidazol-4-one Chemical compound C1=NC(OC)=CC=C1C(N1C)=NC2=C1C(=O)N(C1=CN(C)C(=O)C(C)=C1)[C@@H]2C1=CC=C(Cl)C=C1 MZKIOOQWOZDDMX-OAQYLSRUSA-N 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- IWTFOFMTUOBLHG-UHFFFAOYSA-N 2-methoxypyridine Chemical compound COC1=CC=CC=N1 IWTFOFMTUOBLHG-UHFFFAOYSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- SDLMPYCGZKLARA-UHFFFAOYSA-N 3-tert-butyl-4-(4-chlorophenyl)-2-cyclopropyl-5-(1,5-dimethyl-6-oxopyridin-3-yl)-4h-pyrrolo[3,4-d]imidazol-6-one Chemical compound CN1C(=O)C(C)=CC(N2C(C3=C(N(C(C4CC4)=N3)C(C)(C)C)C2C=2C=CC(Cl)=CC=2)=O)=C1 SDLMPYCGZKLARA-UHFFFAOYSA-N 0.000 claims 1
- OTZHGAAUXLOJFP-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-(2,4-dimethoxypyrimidin-5-yl)-5-(3,7-dimethyl-1,2-benzoxazol-5-yl)-3-propan-2-yl-4h-pyrrolo[3,4-d]imidazol-6-one Chemical compound COC1=NC(OC)=NC=C1C(N1C(C)C)=NC2=C1C(C=1C=CC(Cl)=CC=1)N(C=1C=C3C(C)=NOC3=C(C)C=1)C2=O OTZHGAAUXLOJFP-UHFFFAOYSA-N 0.000 claims 1
- CQPGVZBZRUVJJZ-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-(2,4-dimethoxypyrimidin-5-yl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-propan-2-yl-4h-pyrrolo[3,4-d]imidazol-6-one Chemical compound COC1=NC(OC)=NC=C1C(N1C(C)C)=NC2=C1C(C=1C=CC(Cl)=CC=1)N(C1=CN3C(C)=NN=C3C(C)=C1)C2=O CQPGVZBZRUVJJZ-UHFFFAOYSA-N 0.000 claims 1
- BUFWGONUWXTMGP-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-(2,5-dihydrofuran-3-yl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-propan-2-yl-4h-pyrrolo[3,4-d]imidazol-6-one Chemical compound C1=2N(C(C)C)C(C=3COCC=3)=NC=2C(=O)N(C2=CN3C(C)=NN=C3C(C)=C2)C1C1=CC=C(Cl)C=C1 BUFWGONUWXTMGP-UHFFFAOYSA-N 0.000 claims 1
- IQIUDSWFPYGIST-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-(3,5-dimethyl-1,2-oxazol-4-yl)-5-(1,5-dimethyl-6-oxopyridin-3-yl)-3-propan-2-yl-4h-pyrrolo[3,4-d]imidazol-6-one Chemical compound C1=2N(C(C)C)C(C3=C(ON=C3C)C)=NC=2C(=O)N(C2=CN(C)C(=O)C(C)=C2)C1C1=CC=C(Cl)C=C1 IQIUDSWFPYGIST-UHFFFAOYSA-N 0.000 claims 1
- NJQDQDHZAAGIQX-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-cyclopentyl-5-(1,5-dimethyl-6-oxopyridin-3-yl)-3-propan-2-yl-4h-pyrrolo[3,4-d]imidazol-6-one Chemical compound C1=2N(C(C)C)C(C3CCCC3)=NC=2C(=O)N(C2=CN(C)C(=O)C(C)=C2)C1C1=CC=C(Cl)C=C1 NJQDQDHZAAGIQX-UHFFFAOYSA-N 0.000 claims 1
- LMLJGVCFCYGAST-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-cyclopropyl-5-(1,5-dimethyl-6-oxopyridin-3-yl)-3-propan-2-yl-4h-pyrrolo[3,4-d]imidazol-6-one Chemical compound C1=2N(C(C)C)C(C3CC3)=NC=2C(=O)N(C2=CN(C)C(=O)C(C)=C2)C1C1=CC=C(Cl)C=C1 LMLJGVCFCYGAST-UHFFFAOYSA-N 0.000 claims 1
- HQEUJXGKBKBFIW-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-cyclopropyl-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-propan-2-yl-4h-pyrrolo[3,4-d]imidazol-6-one Chemical compound C1=2N(C(C)C)C(C3CC3)=NC=2C(=O)N(C2=CN3C(C)=NN=C3C(C)=C2)C1C1=CC=C(Cl)C=C1 HQEUJXGKBKBFIW-UHFFFAOYSA-N 0.000 claims 1
- ULIAHCSBBVNLGS-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-cyclopropyl-5-(8-methoxy-3-methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-propan-2-yl-4h-pyrrolo[3,4-d]imidazol-6-one Chemical compound C=1N2C(C)=NN=C2C(OC)=CC=1N(C1=O)C(C=2C=CC(Cl)=CC=2)C(N2C(C)C)=C1N=C2C1CC1 ULIAHCSBBVNLGS-UHFFFAOYSA-N 0.000 claims 1
- OENGVXVRDHPNME-UHFFFAOYSA-N 4-(4-chlorophenyl)-3-cyclopropyl-5-(1,5-dimethyl-6-oxopyridin-3-yl)-2-(1,3-thiazol-2-yl)-4h-pyrrolo[3,4-d]imidazol-6-one Chemical compound CN1C(=O)C(C)=CC(N2C(C3=C(N(C(C=4SC=CN=4)=N3)C3CC3)C2C=2C=CC(Cl)=CC=2)=O)=C1 OENGVXVRDHPNME-UHFFFAOYSA-N 0.000 claims 1
- PMIMBFPXSMELLC-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-(1,5-dimethyl-6-oxopyridin-3-yl)-2-(2,4-dimethyl-1,3-thiazol-5-yl)-3-propan-2-yl-4h-pyrrolo[3,4-d]imidazol-6-one Chemical compound C1=2N(C(C)C)C(C3=C(N=C(C)S3)C)=NC=2C(=O)N(C2=CN(C)C(=O)C(C)=C2)C1C1=CC=C(Cl)C=C1 PMIMBFPXSMELLC-UHFFFAOYSA-N 0.000 claims 1
- WKAWRKNMCTXBMF-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-(1,5-dimethyl-6-oxopyridin-3-yl)-2-(2-fluoropyridin-3-yl)-3-methyl-4h-pyrrolo[3,4-d]imidazol-6-one Chemical compound CN1C(=O)C(C)=CC(N2C(C3=C(N(C(C=4C(=NC=CC=4)F)=N3)C)C2C=2C=CC(Cl)=CC=2)=O)=C1 WKAWRKNMCTXBMF-UHFFFAOYSA-N 0.000 claims 1
- OVLDCYAZEIXCEQ-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-(1,5-dimethyl-6-oxopyridin-3-yl)-2-(2-methyl-1,3-thiazol-5-yl)-3-propan-2-yl-4h-pyrrolo[3,4-d]imidazol-6-one Chemical compound C1=2N(C(C)C)C(C=3SC(C)=NC=3)=NC=2C(=O)N(C2=CN(C)C(=O)C(C)=C2)C1C1=CC=C(Cl)C=C1 OVLDCYAZEIXCEQ-UHFFFAOYSA-N 0.000 claims 1
- UWHQJIJZHLHELR-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-(1,5-dimethyl-6-oxopyridin-3-yl)-2-(6-methoxypyridin-3-yl)-3-methyl-4h-pyrrolo[3,4-d]imidazol-6-one Chemical compound C1=NC(OC)=CC=C1C(N1C)=NC2=C1C(C=1C=CC(Cl)=CC=1)N(C1=CN(C)C(=O)C(C)=C1)C2=O UWHQJIJZHLHELR-UHFFFAOYSA-N 0.000 claims 1
- IMXDUOIANVGJIA-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-(1,5-dimethyl-6-oxopyridin-3-yl)-3-propan-2-yl-2-(1,3-thiazol-2-yl)-4h-pyrrolo[3,4-d]imidazol-6-one Chemical compound C1=2N(C(C)C)C(C=3SC=CN=3)=NC=2C(=O)N(C2=CN(C)C(=O)C(C)=C2)C1C1=CC=C(Cl)C=C1 IMXDUOIANVGJIA-UHFFFAOYSA-N 0.000 claims 1
- MLQZIRMMNHSJKH-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-(1,5-dimethyl-6-oxopyridin-3-yl)-3-propan-2-yl-2-(1,3-thiazol-5-yl)-4h-pyrrolo[3,4-d]imidazol-6-one Chemical compound C1=2N(C(C)C)C(C=3SC=NC=3)=NC=2C(=O)N(C2=CN(C)C(=O)C(C)=C2)C1C1=CC=C(Cl)C=C1 MLQZIRMMNHSJKH-UHFFFAOYSA-N 0.000 claims 1
- DNXFUDZUKZRLEU-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-(1-methyl-6-oxopyridin-3-yl)-2-(1,2-oxazol-4-yl)-3-propan-2-yl-4h-pyrrolo[3,4-d]imidazol-6-one Chemical compound C1=2N(C(C)C)C(C3=CON=C3)=NC=2C(=O)N(C2=CN(C)C(=O)C=C2)C1C1=CC=C(Cl)C=C1 DNXFUDZUKZRLEU-UHFFFAOYSA-N 0.000 claims 1
- WXZFQCVRGXOYGQ-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-(1-methyl-6-oxopyridin-3-yl)-2-(1-methylpyrazol-3-yl)-3-propan-2-yl-4H-pyrrolo[3,4-d]imidazol-6-one Chemical compound CC(C)n1c(nc2C(=O)N(C(c12)c1ccc(Cl)cc1)c1ccc(=O)n(C)c1)-c1ccn(C)n1 WXZFQCVRGXOYGQ-UHFFFAOYSA-N 0.000 claims 1
- FYEHQUXVXRMVBS-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-(1-methyl-6-oxopyridin-3-yl)-2-(2-methylpyrazol-3-yl)-3-propan-2-yl-4h-pyrrolo[3,4-d]imidazol-6-one Chemical compound C1=2N(C(C)C)C(C=3N(N=CC=3)C)=NC=2C(=O)N(C2=CN(C)C(=O)C=C2)C1C1=CC=C(Cl)C=C1 FYEHQUXVXRMVBS-UHFFFAOYSA-N 0.000 claims 1
- RWRYTMPXTGYISG-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-(3,7-dimethyl-1,2-benzoxazol-5-yl)-2-(6-methoxypyridin-3-yl)-3-propan-2-yl-4h-pyrrolo[3,4-d]imidazol-6-one Chemical compound C1=NC(OC)=CC=C1C(N1C(C)C)=NC2=C1C(C=1C=CC(Cl)=CC=1)N(C=1C=C3C(C)=NOC3=C(C)C=1)C2=O RWRYTMPXTGYISG-UHFFFAOYSA-N 0.000 claims 1
- YJEIXSZAEKFWTM-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-(3,7-dimethylbenzotriazol-5-yl)-2-methyl-3-propan-2-yl-4h-pyrrolo[3,4-d]imidazol-6-one Chemical compound C1=2N(C(C)C)C(C)=NC=2C(=O)N(C=2C=C3N(C)N=NC3=C(C)C=2)C1C1=CC=C(Cl)C=C1 YJEIXSZAEKFWTM-UHFFFAOYSA-N 0.000 claims 1
- SNDFCVARRAHINB-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-2-(1,3-oxazol-2-yl)-3-propan-2-yl-4h-pyrrolo[3,4-d]imidazol-6-one Chemical compound C1=2N(C(C)C)C(C=3OC=CN=3)=NC=2C(=O)N(C2=CN3C(C)=NN=C3C(C)=C2)C1C1=CC=C(Cl)C=C1 SNDFCVARRAHINB-UHFFFAOYSA-N 0.000 claims 1
- GLMGIYSAZNFOHX-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-2-(1-methyl-3,6-dihydro-2h-pyridin-5-yl)-3-propan-2-yl-4h-pyrrolo[3,4-d]imidazol-6-one Chemical compound C1=2N(C(C)C)C(C=3CN(C)CCC=3)=NC=2C(=O)N(C2=CN3C(C)=NN=C3C(C)=C2)C1C1=CC=C(Cl)C=C1 GLMGIYSAZNFOHX-UHFFFAOYSA-N 0.000 claims 1
- IOHXSSTYGFWMFM-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-2-(6-methoxypyridin-3-yl)-3-propan-2-yl-4h-pyrrolo[3,4-d]imidazol-6-one Chemical compound C1=NC(OC)=CC=C1C(N1C(C)C)=NC2=C1C(C=1C=CC(Cl)=CC=1)N(C1=CN3C(C)=NN=C3C(C)=C1)C2=O IOHXSSTYGFWMFM-UHFFFAOYSA-N 0.000 claims 1
- KJSPRHSFQGRYOT-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-2-methyl-3-propan-2-yl-4h-pyrrolo[3,4-d]imidazol-6-one Chemical compound C1=2N(C(C)C)C(C)=NC=2C(=O)N(C2=NN3C(C)=NN=C3C(C)=C2)C1C1=CC=C(Cl)C=C1 KJSPRHSFQGRYOT-UHFFFAOYSA-N 0.000 claims 1
- JEBJXGHLBZQKNY-UHFFFAOYSA-N 5-[6-(4-chlorophenyl)-5-(1,5-dimethyl-6-oxopyridin-3-yl)-4-oxo-3-propyl-6h-pyrrolo[3,4-d]imidazol-2-yl]pyridine-3-carbonitrile Chemical compound O=C1C=2N(CCC)C(C=3C=C(C=NC=3)C#N)=NC=2C(C=2C=CC(Cl)=CC=2)N1C=1C=C(C)C(=O)N(C)C=1 JEBJXGHLBZQKNY-UHFFFAOYSA-N 0.000 claims 1
- CBNDXTMVECMPGV-UHFFFAOYSA-N 6-(4-chlorophenyl)-5-(1,5-dimethyl-6-oxopyridin-3-yl)-2-(2-methoxypyridin-3-yl)-3-propan-2-yl-6h-pyrrolo[3,4-d]imidazol-4-one Chemical compound COC1=NC=CC=C1C(N1C(C)C)=NC2=C1C(=O)N(C1=CN(C)C(=O)C(C)=C1)C2C1=CC=C(Cl)C=C1 CBNDXTMVECMPGV-UHFFFAOYSA-N 0.000 claims 1
- SOSVCXWWZFMQQP-UHFFFAOYSA-N 6-(4-chlorophenyl)-5-(1,5-dimethyl-6-oxopyridin-3-yl)-2-(5-fluoro-2-methoxypyridin-4-yl)-3-propyl-6h-pyrrolo[3,4-d]imidazol-4-one Chemical compound O=C1C=2N(CCC)C(C=3C(=CN=C(OC)C=3)F)=NC=2C(C=2C=CC(Cl)=CC=2)N1C=1C=C(C)C(=O)N(C)C=1 SOSVCXWWZFMQQP-UHFFFAOYSA-N 0.000 claims 1
- XNRZMTWJFLFRMR-UHFFFAOYSA-N 6-(4-chlorophenyl)-5-(1,5-dimethyl-6-oxopyridin-3-yl)-2-(6-methoxypyridin-3-yl)-1,6-dihydropyrrolo[3,4-d]imidazol-4-one Chemical compound C1=NC(OC)=CC=C1C(N1)=NC2=C1C(C=1C=CC(Cl)=CC=1)N(C1=CN(C)C(=O)C(C)=C1)C2=O XNRZMTWJFLFRMR-UHFFFAOYSA-N 0.000 claims 1
- MZKIOOQWOZDDMX-UHFFFAOYSA-N 6-(4-chlorophenyl)-5-(1,5-dimethyl-6-oxopyridin-3-yl)-2-(6-methoxypyridin-3-yl)-3-methyl-6h-pyrrolo[3,4-d]imidazol-4-one Chemical compound C1=NC(OC)=CC=C1C(N1C)=NC2=C1C(=O)N(C1=CN(C)C(=O)C(C)=C1)C2C1=CC=C(Cl)C=C1 MZKIOOQWOZDDMX-UHFFFAOYSA-N 0.000 claims 1
- OSOMHZBGIZCTKM-UHFFFAOYSA-N 6-(4-chlorophenyl)-5-(1,5-dimethyl-6-oxopyridin-3-yl)-3-ethyl-2-(2-methoxypyridin-3-yl)-6h-pyrrolo[3,4-d]imidazol-4-one Chemical compound O=C1C=2N(CC)C(C=3C(=NC=CC=3)OC)=NC=2C(C=2C=CC(Cl)=CC=2)N1C=1C=C(C)C(=O)N(C)C=1 OSOMHZBGIZCTKM-UHFFFAOYSA-N 0.000 claims 1
- SUIIIOQGACLJMI-UHFFFAOYSA-N 6-(4-chlorophenyl)-5-(1,5-dimethyl-6-oxopyridin-3-yl)-3-ethyl-2-(2-methylpyrazol-3-yl)-6h-pyrrolo[3,4-d]imidazol-4-one Chemical compound O=C1C=2N(CC)C(C=3N(N=CC=3)C)=NC=2C(C=2C=CC(Cl)=CC=2)N1C=1C=C(C)C(=O)N(C)C=1 SUIIIOQGACLJMI-UHFFFAOYSA-N 0.000 claims 1
- FQEWVABJRCOJBI-UHFFFAOYSA-N 6-(4-chlorophenyl)-5-(1,5-dimethyl-6-oxopyridin-3-yl)-3-ethyl-2-(6-methoxypyridin-3-yl)-6h-pyrrolo[3,4-d]imidazol-4-one Chemical compound O=C1C=2N(CC)C(C=3C=NC(OC)=CC=3)=NC=2C(C=2C=CC(Cl)=CC=2)N1C=1C=C(C)C(=O)N(C)C=1 FQEWVABJRCOJBI-UHFFFAOYSA-N 0.000 claims 1
- DAXLHHYYMDQRCH-UHFFFAOYSA-N 6-(4-chlorophenyl)-5-(3,7-dimethylbenzotriazol-5-yl)-2-methyl-1,6-dihydropyrrolo[3,4-d]imidazol-4-one Chemical compound C1=2NC(C)=NC=2C(=O)N(C=2C=C3N(C)N=NC3=C(C)C=2)C1C1=CC=C(Cl)C=C1 DAXLHHYYMDQRCH-UHFFFAOYSA-N 0.000 claims 1
- GQVNARRVGGOXNP-UHFFFAOYSA-N 6-(4-chlorophenyl)-5-(3,7-dimethylbenzotriazol-5-yl)-2-methyl-3-propan-2-yl-6h-pyrrolo[3,4-d]imidazol-4-one Chemical compound C=1C(C)=C2N=NN(C)C2=CC=1N1C(=O)C=2N(C(C)C)C(C)=NC=2C1C1=CC=C(Cl)C=C1 GQVNARRVGGOXNP-UHFFFAOYSA-N 0.000 claims 1
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims 1
- 235000018936 Vitellaria paradoxa Nutrition 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 230000004952 protein activity Effects 0.000 claims 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13169390.5 | 2013-05-27 | ||
| EP13169390 | 2013-05-27 | ||
| EP13177676 | 2013-07-23 | ||
| EP13177676.7 | 2013-07-23 | ||
| PCT/IB2014/061715 WO2014191894A1 (en) | 2013-05-27 | 2014-05-26 | Imidazopyrrolidinone derivatives and their use in the treatment of disease |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016520116A JP2016520116A (ja) | 2016-07-11 |
| JP2016520116A5 true JP2016520116A5 (enExample) | 2017-07-06 |
| JP6373978B2 JP6373978B2 (ja) | 2018-08-15 |
Family
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| EP (2) | EP3004109A1 (enExample) |
| JP (1) | JP6373978B2 (enExample) |
| KR (1) | KR20160012194A (enExample) |
| CN (1) | CN105209467B (enExample) |
| AU (1) | AU2014272774B2 (enExample) |
| BR (1) | BR112015029491A2 (enExample) |
| CA (1) | CA2913697A1 (enExample) |
| EA (1) | EA029312B1 (enExample) |
| MX (1) | MX2015016344A (enExample) |
| WO (1) | WO2014191894A1 (enExample) |
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| US9227985B2 (en) | 2013-03-15 | 2016-01-05 | Incyte Corporation | Tricyclic heterocycles as bet protein inhibitors |
| CA2913697A1 (en) | 2013-05-27 | 2014-12-04 | Novartis Ag | Imidazopyrrolidinone derivatives and their use in the treatment of disease |
| SG11201510409QA (en) | 2013-06-21 | 2016-01-28 | Zenith Epigenetics Corp | Novel bicyclic bromodomain inhibitors |
| WO2015004533A2 (en) | 2013-06-21 | 2015-01-15 | Zenith Epigenetics Corp. | Novel substituted bicyclic compounds as bromodomain inhibitors |
| EP3019502B1 (en) | 2013-07-08 | 2017-05-17 | Incyte Holdings Corporation | Tricyclic heterocycles as bet protein inhibitors |
| AU2014298051B2 (en) | 2013-07-31 | 2018-11-15 | Zenith Epigenetics Ltd. | Novel quinazolinones as bromodomain inhibitors |
| DK3290407T3 (da) | 2013-10-18 | 2020-03-23 | Celgene Quanticel Res Inc | Bromodomæneinhibitorer |
| MX2016006667A (es) * | 2013-11-21 | 2016-07-26 | Novartis Ag | Derivados de pirrolo-pirrolona y su uso como inhibidores. |
| WO2015081189A1 (en) | 2013-11-26 | 2015-06-04 | Incyte Corporation | Bicyclic heterocycles as bet protein inhibitors |
| US9399640B2 (en) | 2013-11-26 | 2016-07-26 | Incyte Corporation | Substituted pyrrolo[2,3-c]pyridines and pyrazolo[3,4-c]pyridines as BET protein inhibitors |
| US9309246B2 (en) | 2013-12-19 | 2016-04-12 | Incyte Corporation | Tricyclic heterocycles as BET protein inhibitors |
| MY180775A (en) | 2014-04-23 | 2020-12-09 | Incyte Corp | 1h-pyrrolo[2,3-c]pyridin-7(6h)-ones and pyrazolo[3,4-c]pyridin-7(6h)-ones as inhibitors of bet proteins |
| US9527864B2 (en) | 2014-09-15 | 2016-12-27 | Incyte Corporation | Tricyclic heterocycles as BET protein inhibitors |
| WO2016087936A1 (en) | 2014-12-01 | 2016-06-09 | Zenith Epigenetics Corp. | Substituted pyridinones as bromodomain inhibitors |
| WO2016087942A1 (en) | 2014-12-01 | 2016-06-09 | Zenith Epigenetics Corp. | Substituted pyridines as bromodomain inhibitors |
| CN107207474B (zh) * | 2014-12-11 | 2021-05-07 | 恒翼生物医药科技(上海)有限公司 | 被取代的杂环作为溴结构域抑制剂 |
| CA2966450A1 (en) | 2014-12-17 | 2016-06-23 | Olesya KHARENKO | Inhibitors of bromodomains |
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| AR104259A1 (es) * | 2015-04-15 | 2017-07-05 | Celgene Quanticel Res Inc | Inhibidores de bromodominio |
| WO2017075377A1 (en) | 2015-10-29 | 2017-05-04 | Incyte Corporation | Amorphous solid form of a bet protein inhibitor |
| MX2018009870A (es) | 2016-02-15 | 2018-11-29 | Cemm Forschungszentrum Fuer Molekulare Medizin Gmbh | Inhibidores de taf1 para la terapia del cancer. |
| KR102643344B1 (ko) | 2016-06-20 | 2024-03-07 | 인사이트 코포레이션 | Bet 저해제의 결정질 고체 형태 |
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| US20190262355A1 (en) | 2016-11-14 | 2019-08-29 | Cemm-Forschungszentrum Für Molekulare Medizin Gmbh | Combination of a brd4 inhibitor and an antifolate for the therapy of cancer |
| AU2018208422B2 (en) | 2017-01-10 | 2021-11-11 | Bayer Aktiengesellschaft | Heterocyclene derivatives as pest control agents |
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| WO2018161871A1 (zh) * | 2017-03-06 | 2018-09-13 | 罗欣生物科技（上海）有限公司 | 作为p53-MDM2抑制剂的咪唑并吡咯酮化合物 |
| KR20190129889A (ko) * | 2017-03-31 | 2019-11-20 | 노파르티스 아게 | 혈액 종양에서 HDM2-p53 상호작용 억제제의 용량 및 요법 |
| US11098017B2 (en) * | 2017-09-28 | 2021-08-24 | The General Hospital Corporation | Compounds for treating disorders associated with abnormal steroidogenesis |
| WO2019154329A1 (zh) * | 2018-02-06 | 2019-08-15 | 上海海和药物研究开发有限公司 | 具有bet抑制活性的化合物及其制备方法和用途 |
| JP7358372B2 (ja) * | 2018-03-12 | 2023-10-10 | 羅欣薬業（上海）有限公司 | イミダゾピロロン化合物及びその使用 |
| JPWO2020189525A1 (enExample) * | 2019-03-15 | 2020-09-24 | ||
| CN114096541B (zh) * | 2019-09-12 | 2023-04-04 | 罗欣药业(上海)有限公司 | 一种p53-MDM2抑制剂的晶型及其制备方法 |
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-
2014
- 2014-05-26 CA CA2913697A patent/CA2913697A1/en not_active Abandoned
- 2014-05-26 WO PCT/IB2014/061715 patent/WO2014191894A1/en not_active Ceased
- 2014-05-26 EP EP14731798.6A patent/EP3004109A1/en not_active Withdrawn
- 2014-05-26 KR KR1020157036223A patent/KR20160012194A/ko not_active Withdrawn
- 2014-05-26 BR BR112015029491A patent/BR112015029491A2/pt active Search and Examination
- 2014-05-26 EP EP18173244.7A patent/EP3412675A1/en not_active Withdrawn
- 2014-05-26 CN CN201480028176.6A patent/CN105209467B/zh not_active Expired - Fee Related
- 2014-05-26 AU AU2014272774A patent/AU2014272774B2/en not_active Ceased
- 2014-05-26 US US14/892,616 patent/US9890166B2/en not_active Expired - Fee Related
- 2014-05-26 JP JP2016516276A patent/JP6373978B2/ja not_active Expired - Fee Related
- 2014-05-26 EA EA201592256A patent/EA029312B1/ru not_active IP Right Cessation
- 2014-05-26 MX MX2015016344A patent/MX2015016344A/es unknown
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