JP2016520118A5 - - Google Patents
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- Publication number
- JP2016520118A5 JP2016520118A5 JP2016516280A JP2016516280A JP2016520118A5 JP 2016520118 A5 JP2016520118 A5 JP 2016520118A5 JP 2016516280 A JP2016516280 A JP 2016516280A JP 2016516280 A JP2016516280 A JP 2016516280A JP 2016520118 A5 JP2016520118 A5 JP 2016520118A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- pyrazol
- chlorophenyl
- cyclopropyl
- 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.)
- Pending
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- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 29
- 150000001875 compounds Chemical class 0.000 claims description 27
- SEMXWBFSIDIGPO-UHFFFAOYSA-N 1,5-dihydropyrazol-4-one Chemical compound O=C1CNN=C1 SEMXWBFSIDIGPO-UHFFFAOYSA-N 0.000 claims description 20
- -1 3,8-dimethyl- [1,2,4] triazolo [4,3-a] pyridin-6-yl Chemical group 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 206010028980 Neoplasm Diseases 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 201000011510 cancer Diseases 0.000 claims description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- XMRBIQDRTZCVGG-OAQYLSRUSA-N (6r)-6-(4-chlorophenyl)-3-cyclopropyl-5-(3,7-dimethylbenzotriazol-5-yl)-1-methyl-6h-pyrrolo[3,4-c]pyrazol-4-one Chemical compound N=1N(C)C([C@H](N(C2=O)C=3C=C(C=4N=NN(C)C=4C=3)C)C=3C=CC(Cl)=CC=3)=C2C=1C1CC1 XMRBIQDRTZCVGG-OAQYLSRUSA-N 0.000 claims description 2
- AVVWKDYUXSFEJL-LJQANCHMSA-N (6r)-6-(4-chlorophenyl)-3-cyclopropyl-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-1-methyl-6h-pyrrolo[3,4-c]pyrazol-4-one Chemical compound N=1N(C)C([C@H](N(C2=O)C=3C=C(C)C4=NN=C(N4N=3)C)C=3C=CC(Cl)=CC=3)=C2C=1C1CC1 AVVWKDYUXSFEJL-LJQANCHMSA-N 0.000 claims description 2
- MVAYDDZVYGANLI-HXUWFJFHSA-N (6r)-6-(4-chlorophenyl)-3-cyclopropyl-5-(8-methoxy-3-methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-1-methyl-6h-pyrrolo[3,4-c]pyrazol-4-one Chemical compound N=1N(C)C([C@H](N(C2=O)C=3C=C(C4=NN=C(C)N4C=3)OC)C=3C=CC(Cl)=CC=3)=C2C=1C1CC1 MVAYDDZVYGANLI-HXUWFJFHSA-N 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000004952 protein activity Effects 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
- IWTFOFMTUOBLHG-UHFFFAOYSA-N 2-methoxypyridine Chemical compound COC1=CC=CC=N1 IWTFOFMTUOBLHG-UHFFFAOYSA-N 0.000 claims 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 2
- SCOGYYPZUPWMLU-JOCHJYFZSA-N (6r)-6-(4-chlorophenyl)-3-cyclopropyl-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-1-(2-methoxyethyl)-6h-pyrrolo[3,4-c]pyrazol-4-one Chemical compound C=1([C@H](N(C(=O)C=11)C2=CN3C(C)=NN=C3C(C)=C2)C=2C=CC(Cl)=CC=2)N(CCOC)N=C1C1CC1 SCOGYYPZUPWMLU-JOCHJYFZSA-N 0.000 claims 1
- NCLGWTFZOQZNIS-GHTZIAJQSA-N (6r)-6-(4-chlorophenyl)-3-cyclopropyl-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-1-[(2s)-3,3,3-trifluoro-2-hydroxypropyl]-6h-pyrrolo[3,4-c]pyrazol-4-one Chemical compound N=1N(C[C@H](O)C(F)(F)F)C([C@H](N(C2=O)C=3C=C(C)C4=NN=C(N4C=3)C)C=3C=CC(Cl)=CC=3)=C2C=1C1CC1 NCLGWTFZOQZNIS-GHTZIAJQSA-N 0.000 claims 1
- ZBIYSSHSZQVNSP-GOSISDBHSA-N (6r)-6-(4-chlorophenyl)-3-cyclopropyl-5-[3-(difluoromethyl)-8-methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl]-1-methyl-6h-pyrrolo[3,4-c]pyrazol-4-one Chemical compound N=1N(C)C([C@H](N(C2=O)C=3C=C(C4=NN=C(N4C=3)C(F)F)C)C=3C=CC(Cl)=CC=3)=C2C=1C1CC1 ZBIYSSHSZQVNSP-GOSISDBHSA-N 0.000 claims 1
- JBWFCYLPISSKIG-HXUWFJFHSA-N (6r)-6-(4-chlorophenyl)-3-cyclopropyl-5-[3-(fluoromethyl)-8-methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl]-1-methyl-6h-pyrrolo[3,4-c]pyrazol-4-one Chemical compound N=1N(C)C([C@H](N(C2=O)C=3C=C(C4=NN=C(CF)N4C=3)C)C=3C=CC(Cl)=CC=3)=C2C=1C1CC1 JBWFCYLPISSKIG-HXUWFJFHSA-N 0.000 claims 1
- XZYFNQNYLMTZIS-JOCHJYFZSA-N (6r)-6-(4-chlorophenyl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-(2-methoxypyridin-3-yl)-1-methyl-6h-pyrrolo[3,4-c]pyrazol-4-one Chemical compound COC1=NC=CC=C1C1=NN(C)C2=C1C(=O)N(C1=CN3C(C)=NN=C3C(C)=C1)[C@@H]2C1=CC=C(Cl)C=C1 XZYFNQNYLMTZIS-JOCHJYFZSA-N 0.000 claims 1
- FRDVUWTYVBTBSE-UHFFFAOYSA-N 5-(8-amino-3-methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-6-(4-chlorophenyl)-3-cyclopropyl-1-methyl-6h-pyrrolo[3,4-c]pyrazol-4-one Chemical compound C=1N2C(C)=NN=C2C(N)=CC=1N(C1=O)C(C=2C=CC(Cl)=CC=2)C(N(N=2)C)=C1C=2C1CC1 FRDVUWTYVBTBSE-UHFFFAOYSA-N 0.000 claims 1
- ADWUQOKWKQHUJB-FTYDEUEMSA-N 5-[(2R,4E)-4-[amino(cyclopropyl)methylidene]-2-(4-chlorophenyl)-3-methylimino-5-oxopyrrolidin-1-yl]-1,3-dimethylpyridin-2-one Chemical compound CC1=CC(=CN(C1=O)C)N2[C@@H](C(=NC)/C(=C(/C3CC3)\N)/C2=O)C4=CC=C(C=C4)Cl ADWUQOKWKQHUJB-FTYDEUEMSA-N 0.000 claims 1
- SNIKOFNWYKITGY-UHFFFAOYSA-N 6-(4-chlorophenyl)-3-cyclopropyl-5-(3,7-dimethylbenzotriazol-5-yl)-1-(2-methylpyrazol-3-yl)-6h-pyrrolo[3,4-c]pyrazol-4-one Chemical compound C=1C=2N(C)N=NC=2C(C)=CC=1N(C1=O)C(C=2C=CC(Cl)=CC=2)C2=C1C(C1CC1)=NN2C1=CC=NN1C SNIKOFNWYKITGY-UHFFFAOYSA-N 0.000 claims 1
- XMRBIQDRTZCVGG-UHFFFAOYSA-N 6-(4-chlorophenyl)-3-cyclopropyl-5-(3,7-dimethylbenzotriazol-5-yl)-1-methyl-6h-pyrrolo[3,4-c]pyrazol-4-one Chemical compound C=1C=2N(C)N=NC=2C(C)=CC=1N(C1=O)C(C=2C=CC(Cl)=CC=2)C(N(N=2)C)=C1C=2C1CC1 XMRBIQDRTZCVGG-UHFFFAOYSA-N 0.000 claims 1
- YTFVGFPLAOYSNF-UHFFFAOYSA-N 6-(4-chlorophenyl)-3-cyclopropyl-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-1-(2-methylpyrazol-3-yl)-6h-pyrrolo[3,4-c]pyrazol-4-one Chemical compound C=1N2C(C)=NN=C2C(C)=CC=1N(C1=O)C(C=2C=CC(Cl)=CC=2)C2=C1C(C1CC1)=NN2C1=CC=NN1C YTFVGFPLAOYSNF-UHFFFAOYSA-N 0.000 claims 1
- ZRAGYVAOZMZDPY-UHFFFAOYSA-N 6-(4-chlorophenyl)-3-cyclopropyl-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-1-methyl-6h-pyrrolo[3,4-c]pyrazol-4-one Chemical compound C=1N2C(C)=NN=C2C(C)=CC=1N(C1=O)C(C=2C=CC(Cl)=CC=2)C(N(N=2)C)=C1C=2C1CC1 ZRAGYVAOZMZDPY-UHFFFAOYSA-N 0.000 claims 1
- MLMDKPAWBXFXNA-UHFFFAOYSA-N 6-(4-chlorophenyl)-3-cyclopropyl-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-1-(2-methylpyrazol-3-yl)-6h-pyrrolo[3,4-c]pyrazol-4-one Chemical compound N=1N2C(C)=NN=C2C(C)=CC=1N(C1=O)C(C=2C=CC(Cl)=CC=2)C2=C1C(C1CC1)=NN2C1=CC=NN1C MLMDKPAWBXFXNA-UHFFFAOYSA-N 0.000 claims 1
- AVVWKDYUXSFEJL-UHFFFAOYSA-N 6-(4-chlorophenyl)-3-cyclopropyl-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-1-methyl-6h-pyrrolo[3,4-c]pyrazol-4-one Chemical compound N=1N2C(C)=NN=C2C(C)=CC=1N(C1=O)C(C=2C=CC(Cl)=CC=2)C(N(N=2)C)=C1C=2C1CC1 AVVWKDYUXSFEJL-UHFFFAOYSA-N 0.000 claims 1
- MDJXFKRWSHUIHK-YMOXTTMHSA-N COc1ncccc1C1NNC2C1C(=O)N([C@@H]2c1ccc(Cl)cc1)c1cc(C)c2nnc(C)n2c1 Chemical compound COc1ncccc1C1NNC2C1C(=O)N([C@@H]2c1ccc(Cl)cc1)c1cc(C)c2nnc(C)n2c1 MDJXFKRWSHUIHK-YMOXTTMHSA-N 0.000 claims 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims 1
- OYDMPDMTZYTSSQ-UHFFFAOYSA-N tert-butyl n-[6-[6-(4-chlorophenyl)-3-cyclopropyl-1-methyl-4-oxo-6h-pyrrolo[3,4-c]pyrazol-5-yl]-3-methyl-[1,2,4]triazolo[4,3-a]pyridin-8-yl]carbamate Chemical compound C=1N2C(C)=NN=C2C(NC(=O)OC(C)(C)C)=CC=1N(C1=O)C(C=2C=CC(Cl)=CC=2)C(N(N=2)C)=C1C=2C1CC1 OYDMPDMTZYTSSQ-UHFFFAOYSA-N 0.000 claims 1
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 description 3
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- GTLGKZJPNAWIBT-UHFFFAOYSA-N ethyl n-[6-[6-(4-chlorophenyl)-3-cyclopropyl-1-methyl-4-oxo-6h-pyrrolo[3,4-c]pyrazol-5-yl]-3-methyl-[1,2,4]triazolo[4,3-a]pyridin-8-yl]carbamate Chemical compound C=1N2C(C)=NN=C2C(NC(=O)OCC)=CC=1N(C1=O)C(C=2C=CC(Cl)=CC=2)C(N(N=2)C)=C1C=2C1CC1 GTLGKZJPNAWIBT-UHFFFAOYSA-N 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13169441.6 | 2013-05-28 | ||
| EP13169441 | 2013-05-28 | ||
| PCT/IB2014/061736 WO2014191906A1 (en) | 2013-05-28 | 2014-05-27 | Pyrazolo-pyrrolidin-4-one derivatives as bet inhibitors and their use in the treatment of disease |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2016520118A JP2016520118A (ja) | 2016-07-11 |
| JP2016520118A5 true JP2016520118A5 (enExample) | 2017-06-29 |
Family
ID=48470849
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016516280A Pending JP2016520118A (ja) | 2013-05-28 | 2014-05-27 | Ｂｅｔ阻害剤としてのピラゾロ−ピロリジン−４−オン誘導体および疾患の処置におけるその使用 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US9624247B2 (enExample) |
| EP (1) | EP3004108B1 (enExample) |
| JP (1) | JP2016520118A (enExample) |
| KR (1) | KR20160012195A (enExample) |
| CN (1) | CN105263934B (enExample) |
| AU (1) | AU2014272695B2 (enExample) |
| BR (1) | BR112015029401A8 (enExample) |
| CA (1) | CA2912986A1 (enExample) |
| EA (1) | EA028175B1 (enExample) |
| ES (1) | ES2656471T3 (enExample) |
| MX (1) | MX2015016421A (enExample) |
| PL (1) | PL3004108T3 (enExample) |
| PT (1) | PT3004108T (enExample) |
| WO (1) | WO2014191906A1 (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9227985B2 (en) | 2013-03-15 | 2016-01-05 | Incyte Corporation | Tricyclic heterocycles as bet protein inhibitors |
| CA2912986A1 (en) | 2013-05-28 | 2014-12-04 | Novartis Ag | Pyrazolo-pyrrolidin-4-one derivatives as bet inhibitors and their use in the treatment of disease |
| EP3019502B1 (en) | 2013-07-08 | 2017-05-17 | Incyte Holdings Corporation | Tricyclic 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 |
| WO2015081189A1 (en) | 2013-11-26 | 2015-06-04 | Incyte Corporation | Bicyclic heterocycles 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 |
| GB201504694D0 (en) | 2015-03-19 | 2015-05-06 | Glaxosmithkline Ip Dev Ltd | Covalent conjugates |
| 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 |
| 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 |
| KR20200101434A (ko) | 2017-12-20 | 2020-08-27 | 베타 파머수티컬 컴퍼니 리미티드 | 브로모도메인 단백질 억제제로서 작동하는 화합물 및 조성물 |
| DK3762004T3 (da) * | 2018-03-05 | 2023-11-27 | Klinikum Rechts Der Isar Der Technischen Univ Muenchen | Behandling af tumorer ved hjælp af en kombination af en oncolytisk adenovirus og en CDK4/6 inhibitor |
| CA3147154A1 (en) * | 2019-07-12 | 2021-01-21 | Scenic Immunology B.V. | N-substituted-3,4-(fused 5-ring)-5-phenyl-pyrrolidine-2-one compounds as inhibitors of isoqc and/or qc enzyme |
| US11833155B2 (en) | 2020-06-03 | 2023-12-05 | Incyte Corporation | Combination therapy for treatment of myeloproliferative neoplasms |
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-
2014
- 2014-05-27 CA CA2912986A patent/CA2912986A1/en not_active Abandoned
- 2014-05-27 MX MX2015016421A patent/MX2015016421A/es unknown
- 2014-05-27 KR KR1020157036224A patent/KR20160012195A/ko not_active Withdrawn
- 2014-05-27 EP EP14728350.1A patent/EP3004108B1/en not_active Not-in-force
- 2014-05-27 US US14/892,623 patent/US9624247B2/en not_active Expired - Fee Related
- 2014-05-27 EA EA201592255A patent/EA028175B1/ru not_active IP Right Cessation
- 2014-05-27 CN CN201480030590.0A patent/CN105263934B/zh not_active Expired - Fee Related
- 2014-05-27 PL PL14728350T patent/PL3004108T3/pl unknown
- 2014-05-27 BR BR112015029401A patent/BR112015029401A8/pt not_active Application Discontinuation
- 2014-05-27 PT PT147283501T patent/PT3004108T/pt unknown
- 2014-05-27 WO PCT/IB2014/061736 patent/WO2014191906A1/en not_active Ceased
- 2014-05-27 JP JP2016516280A patent/JP2016520118A/ja active Pending
- 2014-05-27 ES ES14728350.1T patent/ES2656471T3/es active Active
- 2014-05-27 AU AU2014272695A patent/AU2014272695B2/en not_active Ceased
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