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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| BR112020012084A2 (pt) | 2017-12-19 | 2020-11-24 | Bristol-Myers Squibb Company | compostos de indol substituído úteis como inibidores de tlr |
| JP7328977B2 (ja) | 2018-02-12 | 2023-08-17 | エフ． ホフマン－ラ ロシュ アーゲー | ウイルス感染の処置および予防のための新規のスルホン化合物および誘導体 |
| KR20210018818A (ko) | 2018-06-05 | 2021-02-18 | 에프. 호프만-라 로슈 아게 | 자가면역 질환의 치료를 위한 테트라하이드로-1H-피라지노[2,1-a]이소인돌릴퀴놀린 화합물 |
| 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 |
| WO2020048583A1 (en) | 2018-09-04 | 2020-03-12 | F. Hoffmann-La Roche Ag | Benzothiazole compounds for the treatment of autoimmune diseases |
| WO2020048595A1 (en) | 2018-09-06 | 2020-03-12 | F. Hoffmann-La Roche Ag | Novel cyclic amidine compounds for the treatment of autoimmune disease |
| JP7367004B2 (ja) | 2018-09-06 | 2023-10-23 | エフ． ホフマン－ラ ロシュ アーゲー | 自己免疫疾患の処置のための新規のピラゾロビリジン化合物 |
| US12421240B2 (en) | 2019-10-31 | 2025-09-23 | Hoffmann-La Roche Inc. | Hydropyrazino[1,2-d][1,4]diazepine compounds for the treatment of autoimmune disease |
| JP2023502087A (ja) | 2019-11-19 | 2023-01-20 | エフ．ホフマン－ラ ロシュ アーゲー | 自己免疫疾患の処置のためのヒドロ－１Ｈ－ピロロ［１，２－ａ］ピラジン化合物 |
| JP7649306B2 (ja) | 2019-11-20 | 2025-03-19 | エフ． ホフマン－ラ ロシュ アーゲー | 自己免疫疾患の処置のためのスピロ（イソベンゾフラナゼチジン）化合物 |
| 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 |
| AR123286A1 (es) | 2020-08-19 | 2022-11-16 | Bristol Myers Squibb Co | Compuestos de benzimidazol sustituidos útiles como inhibidores de tlr9 |
| AR123281A1 (es) | 2020-08-19 | 2022-11-16 | Bristol Myers Squibb Co | Compuestos bicíclicos sustituidos útiles como inhibidores de tlr9 |
| AU2021328577A1 (en) | 2020-08-19 | 2023-03-23 | Bristol-Myers Squibb Company | 1H-pyrrolo[3,2-c]pyridine and 1H-pyrrolo[2,3-c]pyridine 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 |
| KR20230171469A (ko) | 2021-04-16 | 2023-12-20 | 길리애드 사이언시즈, 인코포레이티드 | 티에노피롤 화합물 |
| 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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| MX391344B (es) | 2016-07-30 | 2025-03-21 | Bristol Myers Squibb Co | Compuestos indol sustituidos con dimetoxifenilo como inhibidores de receptores tipo toll 7, 8 o 9 (tlr7, tlr8 o tlr9). |
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- 2018-08-03 WO PCT/US2018/045082 patent/WO2019028302A1/en not_active Ceased
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- 2018-08-03 KR KR1020207005967A patent/KR102651947B1/ko active Active
- 2018-08-03 EP EP18756116.2A patent/EP3661926B1/en active Active
- 2018-08-03 JP JP2020505835A patent/JP7104775B2/ja active Active
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