JP2020529433A5 - - Google Patents
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- Publication number
- JP2020529433A5 JP2020529433A5 JP2020505835A JP2020505835A JP2020529433A5 JP 2020529433 A5 JP2020529433 A5 JP 2020529433A5 JP 2020505835 A JP2020505835 A JP 2020505835A JP 2020505835 A JP2020505835 A JP 2020505835A JP 2020529433 A5 JP2020529433 A5 JP 2020529433A5
- Authority
- JP
- Japan
- Prior art keywords
- isopropyl
- indole
- piperidine
- methyl
- indol
- 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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- -1 -C (O) NR x R x Chemical group 0.000 claims 180
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical group C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims 34
- 125000000217 alkyl group Chemical group 0.000 claims 24
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims 20
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 14
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 13
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 12
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 12
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 11
- 150000001875 compounds Chemical class 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 10
- 229910052799 carbon Inorganic materials 0.000 claims 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims 9
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 6
- 125000003386 piperidinyl group Chemical group 0.000 claims 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims 6
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 4
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 4
- RJSNRCXIBJVKJX-UHFFFAOYSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1CCC(CC1)C(F)(F)F)C1=CN(C)C(=O)C(C)=C1 Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1CCC(CC1)C(F)(F)F)C1=CN(C)C(=O)C(C)=C1 RJSNRCXIBJVKJX-UHFFFAOYSA-N 0.000 claims 4
- 125000004122 cyclic group Chemical group 0.000 claims 4
- 125000002757 morpholinyl group Chemical group 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 4
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- 208000023275 Autoimmune disease Diseases 0.000 claims 3
- SBBGZULIWVSWTC-UHFFFAOYSA-N C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(C)C)C=1C=C(C(N(C=1)C)=O)C=1C=NC=NC=1 Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(C)C)C=1C=C(C(N(C=1)C)=O)C=1C=NC=NC=1 SBBGZULIWVSWTC-UHFFFAOYSA-N 0.000 claims 3
- 125000002393 azetidinyl group Chemical group 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 208000037976 chronic inflammation Diseases 0.000 claims 3
- 208000037893 chronic inflammatory disorder Diseases 0.000 claims 3
- 125000003566 oxetanyl group Chemical group 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims 3
- 125000002873 tetrahydrofuranonyl group Chemical group 0.000 claims 3
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims 2
- AQSMJIUDASXMAR-UHFFFAOYSA-N 2-[1-methyl-2-oxo-5-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)pyridin-3-yl]-N-propylacetamide Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C=C(C(N(C1)C)=O)CC(=O)NCCC AQSMJIUDASXMAR-UHFFFAOYSA-N 0.000 claims 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 2
- JLAKCHGEEBPDQI-UHFFFAOYSA-N 4-(4-fluorobenzyl)piperidine Chemical compound C1=CC(F)=CC=C1CC1CCNCC1 JLAKCHGEEBPDQI-UHFFFAOYSA-N 0.000 claims 2
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| EA202091474A1 (ru) | 2017-12-19 | 2020-11-18 | Бристол-Маерс Сквибб Компани | Замещенные индольные соединения, применимые в качестве ингибиторов tlr |
| WO2019155042A1 (en) | 2018-02-12 | 2019-08-15 | F. Hoffmann-La Roche Ag | Novel sulfone compounds and derivatives for the treatment and prophylaxis of virus infection |
| US12157746B2 (en) | 2018-06-05 | 2024-12-03 | Hoffmann-La Roche Inc. | Tetrahydro-1H-pyrazino[2,1-a]isoindolylquinoline compounds for the treatment of autoimmune disease |
| EP3807270B1 (en) | 2018-06-12 | 2023-09-13 | F. Hoffmann-La Roche AG | Novel heteroaryl heterocyclyl compounds for the treatment of autoimmune disease |
| US11952363B2 (en) | 2018-07-23 | 2024-04-09 | Hoffmann-La Roche Inc. | Piperazine compounds for the treatment of autoimmune disease |
| CN112638908A (zh) | 2018-09-04 | 2021-04-09 | 豪夫迈·罗氏有限公司 | 用于治疗自身免疫性疾病的苯并噻唑类化合物 |
| WO2020048596A1 (en) | 2018-09-06 | 2020-03-12 | F. Hoffmann-La Roche Ag | Novel pyrazolopyridine compounds for the treatment of autoimmune disease |
| EP3847170B1 (en) | 2018-09-06 | 2022-06-22 | F. Hoffmann-La Roche AG | Novel cyclic amidine compounds for the treatment of autoimmune disease |
| CN114599652B (zh) | 2019-10-31 | 2024-07-12 | 豪夫迈·罗氏有限公司 | 用于治疗自身免疫性疾病的氢吡嗪并[1,2-d][1,4]二氮杂䓬化合物 |
| EP4061816A1 (en) | 2019-11-19 | 2022-09-28 | F. Hoffmann-La Roche AG | Hydro-1h-pyrrolo[1,2-a]pyrazine compounds for the treatment of autoimmune disease |
| EP4061821B1 (en) | 2019-11-20 | 2025-08-06 | F. Hoffmann-La Roche AG | Spiro(isobenzofuranazetidine) compounds for the treatment of autoimmune disease |
| CN111747926B (zh) * | 2020-06-23 | 2024-01-30 | 浙江华海药业股份有限公司 | 一种羟哌吡酮游离碱的合成工艺改进方法 |
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| EP4200297B1 (en) | 2020-08-19 | 2026-05-13 | Bristol-Myers Squibb Company | Imidazo[1,2-a]pyridine and [1,2,4]triazolo[1,5-a]pyridine derivatives as tlr9 inhibitors for the treatment of fibrosis |
| US12492188B2 (en) | 2020-08-19 | 2025-12-09 | Bristol-Myers Squibb Company | 1H-benzo[D]imidazole derivatives as TLR9 inhibitors for the treatment of fibrosis |
| CN112430632B (zh) * | 2020-11-18 | 2022-09-13 | 上海合全药物研发有限公司 | 2-((反式)-4-氨基环己烷基)异丙醇的制备方法 |
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| CN113604553B (zh) * | 2021-07-27 | 2023-08-15 | 中南大学湘雅二医院 | 成人still’s病生物标志物、诊断试剂及其应用 |
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| KR101823488B1 (ko) | 2013-10-14 | 2018-01-30 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 선택적으로 치환된 퀴놀린 화합물 |
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| CN109715617B (zh) | 2016-07-30 | 2022-04-19 | 百时美施贵宝公司 | 作为tlr7、tlr8或tlr9抑制剂的二甲氧基苯基取代的吲哚化合物 |
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| KR102730859B1 (ko) | 2017-12-20 | 2024-11-15 | 브리스톨-마이어스 스큅 컴퍼니 | 아릴 및 헤테로아릴 치환된 인돌 화합물 |
-
2018
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- 2018-08-03 WO PCT/US2018/045082 patent/WO2019028302A1/en not_active Ceased
- 2018-08-03 JP JP2020505835A patent/JP7104775B2/ja active Active
- 2018-08-03 CN CN201880050864.0A patent/CN110997656B/zh active Active
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