JP2018520105A5 - - Google Patents
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- Publication number
- JP2018520105A5 JP2018520105A5 JP2017560547A JP2017560547A JP2018520105A5 JP 2018520105 A5 JP2018520105 A5 JP 2018520105A5 JP 2017560547 A JP2017560547 A JP 2017560547A JP 2017560547 A JP2017560547 A JP 2017560547A JP 2018520105 A5 JP2018520105 A5 JP 2018520105A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- methyl
- indol
- carbonyl
- compound
- 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
Links
- 125000000217 alkyl group Chemical group 0.000 claims 41
- 150000001875 compounds Chemical class 0.000 claims 12
- 150000003839 salts Chemical class 0.000 claims 12
- 125000001475 halogen functional group Chemical group 0.000 claims 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- -1 -OH Chemical group 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 2
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 239000000178 monomer Substances 0.000 claims 2
- 101100406797 Arabidopsis thaliana PAD4 gene Proteins 0.000 claims 1
- 101150094373 Padi4 gene Proteins 0.000 claims 1
- 102100035731 Protein-arginine deiminase type-4 Human genes 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 206010047115 Vasculitis Diseases 0.000 claims 1
- XCHVAFMDSDWGKU-QGZVFWFLSA-N [(3R)-3-aminopiperidin-1-yl]-[1-methyl-2-[1-(2,2,2-trifluoroethyl)indol-2-yl]benzimidazol-5-yl]methanone Chemical compound CN1C(=NC2=C1C=CC(=C2)C(=O)N1C[C@@H](CCC1)N)C=1N(C2=CC=CC=C2C=1)CC(F)(F)F XCHVAFMDSDWGKU-QGZVFWFLSA-N 0.000 claims 1
- MBBFDDBIJGOKLI-OAQYLSRUSA-N [(3R)-3-aminopiperidin-1-yl]-[1-methyl-2-[1-[(1-methylpyrazol-4-yl)methyl]indol-2-yl]benzimidazol-5-yl]methanone Chemical compound CN1C(=NC2=C1C=CC(=C2)C(=O)N1C[C@@H](CCC1)N)C=1N(C2=CC=CC=C2C=1)CC=1C=NN(C=1)C MBBFDDBIJGOKLI-OAQYLSRUSA-N 0.000 claims 1
- UKEDVRNNFNCFJN-HSZRJFAPSA-N [(3R)-3-aminopiperidin-1-yl]-[2-(1-benzylindol-2-yl)-1-methylbenzimidazol-5-yl]methanone Chemical compound CN1C(=NC2=C1C=CC(=C2)C(=O)N1C[C@@H](CCC1)N)C=1N(C2=CC=CC=C2C=1)CC1=CC=CC=C1 UKEDVRNNFNCFJN-HSZRJFAPSA-N 0.000 claims 1
- JQGQSIFPSQABNF-GOSISDBHSA-N [(3R)-3-aminopiperidin-1-yl]-[2-(1-ethylindol-2-yl)-7-methoxy-1-methylbenzimidazol-5-yl]methanone Chemical compound C(C)N1C(=CC2=CC=CC=C12)C1=NC2=C(N1C)C(=CC(=C2)C(=O)N1C[C@@H](CCC1)N)OC JQGQSIFPSQABNF-GOSISDBHSA-N 0.000 claims 1
- UZZCYFPUQONPSM-HXUWFJFHSA-N [(3R)-3-aminopiperidin-1-yl]-[2-[1-(cyclopropylmethyl)indol-2-yl]-1-methylbenzimidazol-5-yl]methanone Chemical compound CN1C2=CC=C(C=C2N=C1C1=CC2=CC=CC=C2N1CC1CC1)C(=O)N1CCC[C@@H](N)C1 UZZCYFPUQONPSM-HXUWFJFHSA-N 0.000 claims 1
- VWCKDLAMHWKXFJ-HXUWFJFHSA-N [(3R)-3-aminopiperidin-1-yl]-[2-[1-(cyclopropylmethyl)indol-2-yl]-7-methoxy-1-methylbenzimidazol-5-yl]methanone Chemical compound N[C@H]1CN(CCC1)C(=O)C1=CC2=C(N(C(=N2)C=2N(C3=CC=CC=C3C=2)CC2CC2)C)C(=C1)OC VWCKDLAMHWKXFJ-HXUWFJFHSA-N 0.000 claims 1
- ATMQYASCICEAIR-QGZVFWFLSA-N [(3R)-3-aminopiperidin-1-yl]-[7-methoxy-1-methyl-2-[1-(2,2,2-trifluoroethyl)indol-2-yl]benzimidazol-5-yl]methanone Chemical compound N[C@H]1CN(CCC1)C(=O)C1=CC2=C(N(C(=N2)C=2N(C3=CC=CC=C3C=2)CC(F)(F)F)C)C(=C1)OC ATMQYASCICEAIR-QGZVFWFLSA-N 0.000 claims 1
- NNQKKPQSHPCDSU-YADARESESA-N [(3S,4R)-3-amino-4-hydroxypiperidin-1-yl]-[2-[1-(cyclopropylmethyl)indol-2-yl]-1-methylbenzimidazol-5-yl]methanone Chemical compound CN1C2=CC=C(C=C2N=C1C1=CC2=CC=CC=C2N1CC1CC1)C(=O)N1CC[C@@H](O)[C@@H](N)C1 NNQKKPQSHPCDSU-YADARESESA-N 0.000 claims 1
- FHRGHWJREIVLTF-OXJNMPFZSA-N [(3S,4R)-3-amino-4-hydroxypiperidin-1-yl]-[7-methoxy-1-methyl-2-[1-(2,2,2-trifluoroethyl)indol-2-yl]benzimidazol-5-yl]methanone Chemical compound COC1=C2N(C)C(=NC2=CC(=C1)C(=O)N1CC[C@@H](O)[C@@H](N)C1)C1=CC2=CC=CC=C2N1CC(F)(F)F FHRGHWJREIVLTF-OXJNMPFZSA-N 0.000 claims 1
- 125000003302 alkenyloxy group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([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
- 230000001404 mediated effect Effects 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 125000006413 ring segment Chemical group 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 230000009885 systemic effect Effects 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562164906P | 2015-05-21 | 2015-05-21 | |
| US62/164,906 | 2015-05-21 | ||
| PCT/IB2016/000761 WO2016185279A1 (en) | 2015-05-21 | 2016-05-19 | Benzoimidazole derivatives as pad4 inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018520105A JP2018520105A (ja) | 2018-07-26 |
| JP2018520105A5 true JP2018520105A5 (https=) | 2019-06-20 |
| JP6703553B2 JP6703553B2 (ja) | 2020-06-03 |
Family
ID=56235853
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017560547A Active JP6703553B2 (ja) | 2015-05-21 | 2016-05-19 | Ｐａｄ４阻害剤としてのベンゾイミダゾール誘導体 |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US10407407B2 (https=) |
| EP (1) | EP3298003B1 (https=) |
| JP (1) | JP6703553B2 (https=) |
| KR (1) | KR20180005250A (https=) |
| CN (1) | CN107849015B (https=) |
| AR (1) | AR106863A1 (https=) |
| AU (1) | AU2016264958B2 (https=) |
| BR (1) | BR112017024678A2 (https=) |
| CA (2) | CA2986199C (https=) |
| EA (1) | EA033680B1 (https=) |
| ES (1) | ES2945314T3 (https=) |
| IL (2) | IL255666A (https=) |
| MX (1) | MX387321B (https=) |
| TW (1) | TW201706263A (https=) |
| WO (1) | WO2016185279A1 (https=) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR107032A1 (es) * | 2015-12-09 | 2018-03-14 | Padlock Therapeutics Inc | Inhibidores bicíclicos de pad4 |
| JP6926126B2 (ja) | 2016-02-23 | 2021-08-25 | パドロック・セラピューティクス・インコーポレイテッドＰａｄｌｏｃｋ Ｔｈｅｒａｐｅｕｔｉｃｓ， Ｉｎｃ． | Ｐａｄ４のヘテロアリール阻害剤 |
| KR102398941B1 (ko) * | 2016-07-27 | 2022-05-17 | 패들락 테라퓨틱스, 인코포레이티드 | Pad4의 공유결합성 억제제 |
| JP7118951B2 (ja) | 2016-09-12 | 2022-08-16 | パドロック・セラピューティクス・インコーポレイテッド | Ｐａｄ４のヘテロアリール阻害剤 |
| MX2020003242A (es) * | 2017-09-22 | 2020-09-18 | Jubilant Epipad LLC | Compuestos heterociclicos como inhibidores de pad. |
| AU2018352142B2 (en) * | 2017-10-18 | 2022-08-25 | Jubilant Epipad LLC | Imidazo-pyridine compounds as PAD inhibitors |
| KR20200085836A (ko) | 2017-11-06 | 2020-07-15 | 주빌런트 프로델 엘엘씨 | Pd1/pd-l1 활성화 억제제로서의 피리미딘 유도체 |
| BR112020010322A2 (pt) | 2017-11-24 | 2020-11-17 | Jubilant Episcribe Llc | composto da fórmula i; composto da fórmula ia; composto da fórmula ib; processo de preparação de compostos da fórmula i; composição farmacêutica; método para o tratamento e/ou prevenção de várias doenças; uso dos compostos; método para o tratamento de câncer; e método para o tratamento e/ou prevenção de uma afecção mediada por prmt5 ou um distúrbio proliferativo ou câncer |
| WO2019134985A1 (en) | 2018-01-08 | 2019-07-11 | F. Hoffmann-La Roche Ag | Octahydropyrido[1,2-alpha]pyrazines as magl inhibitors |
| EP3746430A4 (en) | 2018-02-02 | 2021-11-03 | Padforward LLC | INHIBITORS OF PROTEIN ARGININE DEIMINASES |
| SG11202008950PA (en) | 2018-03-13 | 2020-10-29 | Jubilant Prodel LLC | Bicyclic compounds as inhibitors of pd1/pd-l1 interaction/activation |
| PE20201185A1 (es) | 2018-03-22 | 2020-11-03 | Hoffmann La Roche | Inhibidores de la oxacina monoacilglicerol lipasa (magl) |
| CN112789087B (zh) * | 2018-08-08 | 2024-08-13 | 百时美施贵宝公司 | Pad酶的苯并咪唑抑制剂 |
| AU2019319835A1 (en) | 2018-08-08 | 2021-03-25 | Bristol-Myers Squibb Company | Indole and azaindole inhibitors of PAD enzymes |
| EP3833671B1 (en) | 2018-08-08 | 2022-08-24 | Bristol-Myers Squibb Company | Substituted thienopyrroles as pad4 inhibitors |
| WO2020033488A1 (en) * | 2018-08-08 | 2020-02-13 | Bristol-Myers Squibb Company | Substituted benzimidazoles as pad4 inhibitors |
| ES2986417T3 (es) | 2018-08-13 | 2024-11-11 | Hoffmann La Roche | Nuevos compuestos heterocíclicos como inhibidores de la monoacilglicerol lipasa |
| MA53220A (fr) | 2018-08-13 | 2021-11-17 | Hoffmann La Roche | Nouveaux composés hétérocycliques utilisés en tant qu'inhibiteurs de monoacylglycérol lipase |
| ES2955037T3 (es) | 2018-11-22 | 2023-11-28 | Hoffmann La Roche | Nuevos compuestos heterocíclicos |
| US20210094971A1 (en) | 2019-09-09 | 2021-04-01 | Hoffmann-La Roche Inc. | Heterocyclic compounds |
| EP4028403B1 (en) | 2019-09-12 | 2023-11-22 | F. Hoffmann-La Roche AG | 4,4a,5,7,8,8a-hexapyrido[4,3-b][1,4]oxazin-3-one compounds as magl inhibitors |
| CA3155724A1 (en) | 2019-09-24 | 2021-04-01 | F. Hoffmann-La Roche Ag | Heterocyclic compounds |
| EP4034538A1 (en) | 2019-09-24 | 2022-08-03 | F. Hoffmann-La Roche AG | New heterocyclic monoacylglycerol lipase (magl) inhibitors |
| WO2021058443A1 (en) | 2019-09-24 | 2021-04-01 | F. Hoffmann-La Roche Ag | Fluorescent probes for monoacylglycerol lipase (magl) |
| TW202115083A (zh) * | 2019-09-27 | 2021-04-16 | 大陸商南京藥捷安康生物科技有限公司 | 肽醯精胺酸脫亞胺酶抑制劑及其用途 |
| EP4100405A1 (en) * | 2020-02-06 | 2022-12-14 | Bristol-Myers Squibb Company | Macrocyclic pad4 inhibitors useful as immunosuppressant |
| TW202140477A (zh) * | 2020-02-12 | 2021-11-01 | 美商必治妥美雅史谷比公司 | 雜環ｐａｄ４抑制劑 |
| US20230107927A1 (en) | 2020-02-28 | 2023-04-06 | First Wave Bio, Inc. | Methods of treating iatrogenic autoimmune colitis |
| EP4143189A1 (en) * | 2020-04-30 | 2023-03-08 | Gilead Sciences, Inc. | Macrocyclic inhibitors of peptidylarginine deiminases |
| BR112023002553A2 (pt) * | 2020-08-12 | 2023-04-18 | Jubilant Epipad LLC | Composto, composição, uso do composto e uso da composição |
| MX2023002224A (es) | 2020-09-03 | 2023-03-15 | Hoffmann La Roche | Compuestos heterociclicos. |
| WO2022140428A2 (en) | 2020-12-22 | 2022-06-30 | Gilead Sciences, Inc. | Inhibitors of peptidylarginine deiminases |
| TW202241884A (zh) | 2020-12-22 | 2022-11-01 | 美商基利科學股份有限公司 | 肽基精胺酸去亞胺酶之抑制劑 |
| CN118679162A (zh) * | 2021-11-15 | 2024-09-20 | 锐格药业公司 | Pad4抑制剂及其用途 |
| WO2025024265A1 (en) | 2023-07-21 | 2025-01-30 | Bristol-Myers Squibb Company | Methods of assessing citrullination and activity of pad4 modulators |
| WO2026020127A2 (en) | 2024-07-19 | 2026-01-22 | Bristol-Myers Squibb Company | Methods of assessing citrullination and activity of pad2 modulators |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU570439B2 (en) | 1983-03-28 | 1988-03-17 | Compression Labs, Inc. | A combined intraframe and interframe transform coding system |
| US5776963A (en) | 1989-05-19 | 1998-07-07 | Hoechst Marion Roussel, Inc. | 3-(heteroaryl)-1- (2,3-dihydro-1h-isoindol-2-yl)alkyl!pyrrolidines and 3-(heteroaryl)-1- (2,3-dihydro-1h-indol-1-yl)alkyl!pyrrolidines and related compounds and their therapeutic untility |
| AP791A (en) | 1995-04-14 | 1999-12-17 | Glaxo Wellcome Inc | Metered dose inhaler for albuterol. |
| TW533865U (en) | 1997-06-10 | 2003-05-21 | Glaxo Group Ltd | Dispenser for dispensing medicament and actuation indicating device |
| US6119853A (en) | 1998-12-18 | 2000-09-19 | Glaxo Wellcome Inc. | Method and package for storing a pressurized container containing a drug |
| US6390291B1 (en) | 1998-12-18 | 2002-05-21 | Smithkline Beecham Corporation | Method and package for storing a pressurized container containing a drug |
| US6352152B1 (en) | 1998-12-18 | 2002-03-05 | Smithkline Beecham Corporation | Method and package for storing a pressurized container containing a drug |
| US6315112B1 (en) | 1998-12-18 | 2001-11-13 | Smithkline Beecham Corporation | Method and package for storing a pressurized container containing a drug |
| US6448281B1 (en) * | 2000-07-06 | 2002-09-10 | Boehringer Ingelheim (Canada) Ltd. | Viral polymerase inhibitors |
| JP5039268B2 (ja) * | 2001-10-26 | 2012-10-03 | アベンティス・ファーマスーティカルズ・インコーポレイテツド | ベンゾイミダゾールおよび類縁体および蛋白キナーゼ阻害剤としてのその使用 |
| ES2388434T3 (es) | 2003-11-03 | 2012-10-15 | Glaxo Group Limited | Dispositivo de administración de fluido |
| US7429611B2 (en) * | 2004-09-23 | 2008-09-30 | Bristol-Myers Squibb Company | Indole inhibitors of 15-lipoxygenase |
| UY32138A (es) | 2008-09-25 | 2010-04-30 | Boehringer Ingelheim Int | Amidas sustituidas del ácido 2-(2,6-dicloro-fenilamino)-6-fluoro-1-metil-1h-bencimidazol-5-carboxílico y sus sales farmacéuticamente aceptables |
| WO2010115736A2 (en) * | 2009-04-02 | 2010-10-14 | Merck Serono S.A. | Dihydroorotate dehydrogenase inhibitors |
| EP2515655B1 (en) * | 2009-12-21 | 2015-08-05 | Samumed, LLC | 1h-pyrazolo[3,4-beta]pyridines and therapeutic uses thereof |
| RS55684B1 (sr) * | 2012-07-26 | 2017-07-31 | Glaxo Group Ltd | 2-(azaindol-2-il)benzimidazoli kao pad4 inhibitori |
| AR107032A1 (es) * | 2015-12-09 | 2018-03-14 | Padlock Therapeutics Inc | Inhibidores bicíclicos de pad4 |
-
2016
- 2016-05-19 US US15/575,583 patent/US10407407B2/en active Active
- 2016-05-19 CA CA2986199A patent/CA2986199C/en active Active
- 2016-05-19 EP EP16732332.8A patent/EP3298003B1/en active Active
- 2016-05-19 EA EA201792517A patent/EA033680B1/ru not_active IP Right Cessation
- 2016-05-19 JP JP2017560547A patent/JP6703553B2/ja active Active
- 2016-05-19 ES ES16732332T patent/ES2945314T3/es active Active
- 2016-05-19 CN CN201680042358.8A patent/CN107849015B/zh active Active
- 2016-05-19 WO PCT/IB2016/000761 patent/WO2016185279A1/en not_active Ceased
- 2016-05-19 CA CA3199601A patent/CA3199601A1/en active Pending
- 2016-05-19 AU AU2016264958A patent/AU2016264958B2/en active Active
- 2016-05-19 KR KR1020177036327A patent/KR20180005250A/ko not_active Ceased
- 2016-05-19 MX MX2017014714A patent/MX387321B/es unknown
- 2016-05-19 BR BR112017024678-3A patent/BR112017024678A2/pt not_active Application Discontinuation
- 2016-05-20 AR ARP160101486A patent/AR106863A1/es unknown
- 2016-05-20 TW TW105115842A patent/TW201706263A/zh unknown
-
2017
- 2017-11-14 IL IL255666A patent/IL255666A/en active IP Right Grant
-
2019
- 2019-07-18 US US16/515,735 patent/US10815218B2/en active Active
-
2020
- 2020-11-23 IL IL278916A patent/IL278916A/en unknown
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