JP5529876B2 - Mmp−13阻害剤として有用なヘテロアリール置換インドール化合物 - Google Patents
Mmp−13阻害剤として有用なヘテロアリール置換インドール化合物 Download PDFInfo
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- JP5529876B2 JP5529876B2 JP2011532175A JP2011532175A JP5529876B2 JP 5529876 B2 JP5529876 B2 JP 5529876B2 JP 2011532175 A JP2011532175 A JP 2011532175A JP 2011532175 A JP2011532175 A JP 2011532175A JP 5529876 B2 JP5529876 B2 JP 5529876B2
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- PIGKSWUDSOBXMG-UHFFFAOYSA-N CCOC(C(Cc1nc(Br)ccc1[N+](O)=O)=O)=O Chemical compound CCOC(C(Cc1nc(Br)ccc1[N+](O)=O)=O)=O PIGKSWUDSOBXMG-UHFFFAOYSA-N 0.000 description 1
- KAFGTBPOUZUBLP-UHFFFAOYSA-N CCOC(c([nH]c(c1c2)ccc2Br)c1F)=O Chemical compound CCOC(c([nH]c(c1c2)ccc2Br)c1F)=O KAFGTBPOUZUBLP-UHFFFAOYSA-N 0.000 description 1
- OVZZLYJFJOWMTM-UHFFFAOYSA-N CCOC(c1cc(cc(cc2)-c3c[s]c(C(NCc(c(OC)c4)ccc4OC)=O)c3C)c2[nH]1)=O Chemical compound CCOC(c1cc(cc(cc2)-c3c[s]c(C(NCc(c(OC)c4)ccc4OC)=O)c3C)c2[nH]1)=O OVZZLYJFJOWMTM-UHFFFAOYSA-N 0.000 description 1
- XHKMYKCHTBBRKY-UHFFFAOYSA-N CCOC(c1cc(nc(cc2)-c3c(C)[n](COCC[Si](C)(C)C4C=NC=CC(CNC5=O)=C4)c5n3)c2[n]1C(OC(C)(C)C)=O)=O Chemical compound CCOC(c1cc(nc(cc2)-c3c(C)[n](COCC[Si](C)(C)C4C=NC=CC(CNC5=O)=C4)c5n3)c2[n]1C(OC(C)(C)C)=O)=O XHKMYKCHTBBRKY-UHFFFAOYSA-N 0.000 description 1
- FPZAWMRPXSYJJB-UHFFFAOYSA-N CCOC(c1cc2cc(-c3cc(C(NCc(cc4)ccc4C(OC)=O)=O)n[n]3C)ccc2[nH]1)=O Chemical compound CCOC(c1cc2cc(-c3cc(C(NCc(cc4)ccc4C(OC)=O)=O)n[n]3C)ccc2[nH]1)=O FPZAWMRPXSYJJB-UHFFFAOYSA-N 0.000 description 1
- UHHFYGOUQISNPH-UHFFFAOYSA-N CCOC(c1cc2cc(-c3cc(C(NCc4ccc(CC(O)=O)cc4)=O)n[n]3C)ccc2[nH]1)=O Chemical compound CCOC(c1cc2cc(-c3cc(C(NCc4ccc(CC(O)=O)cc4)=O)n[n]3C)ccc2[nH]1)=O UHHFYGOUQISNPH-UHFFFAOYSA-N 0.000 description 1
- IUJWPHRXZDQSQS-UHFFFAOYSA-N CCOC(c1cc2cc(-c3nc(C(NCc(cc4C)ccc4F)=O)ccn3)ccc2[nH]1)=O Chemical compound CCOC(c1cc2cc(-c3nc(C(NCc(cc4C)ccc4F)=O)ccn3)ccc2[nH]1)=O IUJWPHRXZDQSQS-UHFFFAOYSA-N 0.000 description 1
- LWRLKENDQISGEU-UHFFFAOYSA-N CCOC(c1cc2cc(Br)ccc2[nH]1)=O Chemical compound CCOC(c1cc2cc(Br)ccc2[nH]1)=O LWRLKENDQISGEU-UHFFFAOYSA-N 0.000 description 1
- WUHUHIUGKBGHND-UHFFFAOYSA-N CCOC(c1cc2nc([Br]=C)ccc2[nH]1)=O Chemical compound CCOC(c1cc2nc([Br]=C)ccc2[nH]1)=O WUHUHIUGKBGHND-UHFFFAOYSA-N 0.000 description 1
- HPBSGHQXVPAVMT-UHFFFAOYSA-N C[n](c(-c1ccc2[nH]c(-c3cc(F)ncc3)cc2c1)c1)nc1C(NCc(cc1)ccc1C(O)=O)=O Chemical compound C[n](c(-c1ccc2[nH]c(-c3cc(F)ncc3)cc2c1)c1)nc1C(NCc(cc1)ccc1C(O)=O)=O HPBSGHQXVPAVMT-UHFFFAOYSA-N 0.000 description 1
- KMLUNXYSVVORJO-UHFFFAOYSA-N C[n](c(-c1ccc2[nH]c(C3=NCCO3)cc2c1)c1)nc1C(NCc(cc1)ccc1C(O)=O)=O Chemical compound C[n](c(-c1ccc2[nH]c(C3=NCCO3)cc2c1)c1)nc1C(NCc(cc1)ccc1C(O)=O)=O KMLUNXYSVVORJO-UHFFFAOYSA-N 0.000 description 1
- PNIWWLCJFMKBOB-QRVIBDJDSA-N Cc([n](COCC[Si+](C)(C)C)c(C(NCc1ccc(/C=N\C)cc1)=O)n1)c1[Br]=C Chemical compound Cc([n](COCC[Si+](C)(C)C)c(C(NCc1ccc(/C=N\C)cc1)=O)n1)c1[Br]=C PNIWWLCJFMKBOB-QRVIBDJDSA-N 0.000 description 1
- SFNCQGJFYYHXOB-UHFFFAOYSA-N Cc1c(-c(cc2)nc3c2[nH]c(C(O)=O)c3)nc(C(NC2)=O)[n]1COCC[Si+](C)(C)C1C=NC=CC2=C1 Chemical compound Cc1c(-c(cc2)nc3c2[nH]c(C(O)=O)c3)nc(C(NC2)=O)[n]1COCC[Si+](C)(C)C1C=NC=CC2=C1 SFNCQGJFYYHXOB-UHFFFAOYSA-N 0.000 description 1
- MOOFMRGLIRJCRB-UHFFFAOYSA-N Cc1c(-c2ccc3[nH]c(-c4nc(C)n[o]4)cc3c2)nc(C(NCc(cc2)ccc2C#N)=O)[n]1COCC[Si+](C)(C)C Chemical compound Cc1c(-c2ccc3[nH]c(-c4nc(C)n[o]4)cc3c2)nc(C(NCc(cc2)ccc2C#N)=O)[n]1COCC[Si+](C)(C)C MOOFMRGLIRJCRB-UHFFFAOYSA-N 0.000 description 1
- PXQBIZBEKKARDD-UHFFFAOYSA-N Cc1c(-c2ccc3[nH]c(-c4nc(C)n[o]4)cc3c2)nc(CNCc(cc2)ccc2F)[nH]1 Chemical compound Cc1c(-c2ccc3[nH]c(-c4nc(C)n[o]4)cc3c2)nc(CNCc(cc2)ccc2F)[nH]1 PXQBIZBEKKARDD-UHFFFAOYSA-N 0.000 description 1
- KFEWUCOFCOAYQZ-UHFFFAOYSA-N Cc1c[n+]([O-])c(C)cc1 Chemical compound Cc1c[n+]([O-])c(C)cc1 KFEWUCOFCOAYQZ-UHFFFAOYSA-N 0.000 description 1
- MOKOYWUWOZIRMJ-UHFFFAOYSA-N Cc1n[o]c(-c2cc(cc(cc3)-c4cc(C(NCc(cc5)ccc5C(O)=O)=O)ncc4C)c3[nH]2)n1 Chemical compound Cc1n[o]c(-c2cc(cc(cc3)-c4cc(C(NCc(cc5)ccc5C(O)=O)=O)ncc4C)c3[nH]2)n1 MOKOYWUWOZIRMJ-UHFFFAOYSA-N 0.000 description 1
- SJCVIFOMQDAVPH-UHFFFAOYSA-N OC(c1cc(cc(cc2)-c3cc(C(NCc4ccncc4)=O)ncc3)c2[nH]1)=O Chemical compound OC(c1cc(cc(cc2)-c3cc(C(NCc4ccncc4)=O)ncc3)c2[nH]1)=O SJCVIFOMQDAVPH-UHFFFAOYSA-N 0.000 description 1
Classifications
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- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
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- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
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- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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Applications Claiming Priority (3)
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| US10620708P | 2008-10-17 | 2008-10-17 | |
| US61/106,207 | 2008-10-17 | ||
| PCT/US2009/060436 WO2010045188A1 (en) | 2008-10-17 | 2009-10-13 | Heteroaryl substituted indole compounds useful as mmp-13 inhibitors |
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| JP2012505891A JP2012505891A (ja) | 2012-03-08 |
| JP2012505891A5 JP2012505891A5 (esLanguage) | 2012-11-29 |
| JP5529876B2 true JP5529876B2 (ja) | 2014-06-25 |
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| CA (1) | CA2738929A1 (esLanguage) |
| WO (1) | WO2010045188A1 (esLanguage) |
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| EP2344480A1 (en) | 2008-10-15 | 2011-07-20 | Boehringer Ingelheim International GmbH | Fused heteroaryl diamide compounds useful as mmp-13 inhibitors |
| EP2340243B1 (en) | 2008-10-17 | 2014-10-08 | Boehringer Ingelheim International GmbH | Heteroaryl substituted indole compounds useful as mmp-13 inhibitors |
| JP5584696B2 (ja) | 2008-11-17 | 2014-09-03 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Mmp−13阻害剤として有用なヘテロアリールジアミド化合物 |
| MX2012003539A (es) * | 2009-09-24 | 2012-04-30 | Hoffmann La Roche | Derivados de indol como moduladores de los canales de calcio activados por la liberacion de calcio (crac). |
| TWI423962B (zh) * | 2009-10-07 | 2014-01-21 | Lg Life Sciences Ltd | 有效作為黃嘌呤氧化酶抑制劑之新穎化合物、其製備方法及含該化合物之醫藥組成物 |
| KR101913135B1 (ko) | 2011-07-15 | 2018-10-30 | 얀센 파마슈티칼즈, 인코포레이티드 | 감마 세크레타제 조절 인자로서의 신규의 치환 인돌 유도체 |
| CA2844128C (en) | 2011-08-30 | 2020-09-01 | Chdi Foundation, Inc. | Kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof |
| WO2013138600A1 (en) * | 2012-03-16 | 2013-09-19 | Rosen Eliot M | Radioprotector compounds |
| PT3068782T (pt) | 2013-11-13 | 2018-10-08 | Vertex Pharma | Métodos de preparação de inibidores da replicação de vírus da gripe |
| US10730866B2 (en) | 2014-04-07 | 2020-08-04 | Purdue Pharma L.P. | Indole derivatives and use thereof |
| WO2016011316A1 (en) | 2014-07-17 | 2016-01-21 | Chdi Foundation, Inc. | Methods and compositions for treating hiv-related disorders |
| WO2016026078A1 (en) * | 2014-08-19 | 2016-02-25 | Changzhou Jiekai Pharmatech Co., Ltd. | Heterocyclic compounds as erk inhibitors |
| CN108368110A (zh) | 2015-12-07 | 2018-08-03 | 普莱希科公司 | 用于激酶调节的化合物和方法以及其适应症 |
| WO2017165139A1 (en) | 2016-03-25 | 2017-09-28 | St. Jude Children's Research Hospital | 1,4,5-substituted 1,2,3-triazole analogues as antagonists of the pregnane x receptor |
| US10071079B2 (en) | 2016-06-29 | 2018-09-11 | Bristol-Myers Squibb Company | [1,2,4]triazolo[1,5-a]pyridinyl substituted indole compounds |
| AU2017307208B2 (en) | 2016-07-30 | 2021-01-21 | Bristol-Myers Squibb Company | Dimethoxyphenyl substituted indole compounds as TLR7, TLR8 or TLR9 inhibitors |
| JP7028861B2 (ja) | 2016-09-09 | 2022-03-02 | ブリストル-マイヤーズ スクイブ カンパニー | ピリジル置換のインドール化合物 |
| US10428067B2 (en) | 2017-06-07 | 2019-10-01 | Plexxikon Inc. | Compounds and methods for kinase modulation |
| ES2909401T3 (es) | 2017-08-04 | 2022-05-06 | Bristol Myers Squibb Co | Compuestos de indol sustituidos útiles como inhibidores de TLR7/8/9 |
| CN110997670B (zh) | 2017-08-04 | 2022-11-01 | 百时美施贵宝公司 | [1,2,4]三唑并[4,3-a]吡啶基取代的吲哚化合物 |
| KR102849449B1 (ko) | 2017-11-14 | 2025-08-21 | 브리스톨-마이어스 스큅 컴퍼니 | 치환된 인돌 화합물 |
| BR112020011668A2 (pt) | 2017-12-15 | 2020-11-17 | Bristol-Myers Squibb Company | compostos de éter de indol substituído |
| WO2019125977A1 (en) | 2017-12-18 | 2019-06-27 | Bristol-Myers Squibb Company | 4-azaindole compounds |
| CA3085761A1 (en) | 2017-12-19 | 2019-06-27 | Bristol-Myers Squibb Company | Triazole n-linked carbamoylcyclohexyl acids as lpa antagonists |
| SG11202005700SA (en) | 2017-12-19 | 2020-07-29 | Bristol Myers Squibb Co | Amide substituted indole compounds useful as tlr inhibitors |
| EP3728225B1 (en) | 2017-12-19 | 2022-11-09 | Bristol-Myers Squibb Company | Substituted indole compounds useful as tlr inhibitors |
| EP3728188B1 (en) | 2017-12-20 | 2023-10-11 | Bristol-Myers Squibb Company | Aryl and heteroaryl substituted indole compounds |
| SG11202005733QA (en) | 2017-12-20 | 2020-07-29 | Bristol Myers Squibb Co | Diazaindole compounds |
| BR112020011984A2 (pt) | 2017-12-20 | 2020-11-17 | Bristol-Myers Squibb Company | compostos de amino indol úteis como inibidores de tlr |
| WO2019236884A1 (en) | 2018-06-07 | 2019-12-12 | Disarm Therapeutics, Inc. | Inhibitors of sarm1 |
| EP3628669A1 (en) * | 2018-09-28 | 2020-04-01 | GenKyoTex Suisse SA | Novel compounds as nadph oxidase inhibitors |
| US11998537B2 (en) | 2018-10-24 | 2024-06-04 | Bristol-Myers Squibb Company | Substituted indole dimer compounds |
| EP3870583A1 (en) | 2018-10-24 | 2021-09-01 | Bristol-Myers Squibb Company | Substituted indole and indazole compounds |
| US12083114B2 (en) | 2018-12-19 | 2024-09-10 | Disarm Therapeutics, Inc. | Inhibitors of SARM1 in combination with neuro-protective agents |
| WO2020227484A1 (en) | 2019-05-09 | 2020-11-12 | Bristol-Myers Squibb Company | Substituted benzimidazolone compounds |
| KR20220075381A (ko) | 2019-10-01 | 2022-06-08 | 브리스톨-마이어스 스큅 컴퍼니 | 치환된 비시클릭 헤테로아릴 화합물 |
| ES2965164T3 (es) | 2019-10-04 | 2024-04-11 | Bristol Myers Squibb Co | Compuestos de carbazol sustituidos |
| JP7652772B2 (ja) * | 2019-11-01 | 2025-03-27 | ブリストル-マイヤーズ スクイブ カンパニー | 置換ピラゾール化合物 |
| CA3190065A1 (en) | 2020-08-19 | 2022-02-24 | David S. Yoon | Imidazo[1,2-a]pyridine and [1,2,4]triazolo[1,5-a]pyridine derivatives as tlr9 inhibitors for the treatment of fibrosis |
| KR20230053645A (ko) | 2020-08-19 | 2023-04-21 | 브리스톨-마이어스 스큅 컴퍼니 | 섬유증의 치료를 위한 tlr9 억제제로서의 1h-벤조[d]이미다졸 유도체 |
| CN116947821B (zh) * | 2022-04-20 | 2025-10-17 | 成都肯迪特生物医药科技有限公司 | 一种化合物及其在制备jak激酶抑制剂中的用途 |
| US12516051B1 (en) | 2024-09-30 | 2026-01-06 | St. Jude Children's Research Hospital, Inc. | Small molecule degraders and fluorescent probes of PXR |
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| WO2000033836A1 (en) | 1998-12-04 | 2000-06-15 | Ontogen Corporation | 5-membered heterocycles for the treatment of human diseases involving modulators of selectins |
| CA2417638A1 (en) | 2000-07-31 | 2002-02-07 | Smithkline Beecham P.L.C. | Carboxamide compounds and their use as antagonists of a human 11cby receptor |
| GB0018758D0 (en) | 2000-07-31 | 2000-09-20 | Smithkline Beecham Plc | Novel use and compunds |
| WO2002016348A1 (en) | 2000-08-09 | 2002-02-28 | Astrazeneca Ab | Antiangiogenic bicyclic derivatives |
| US7186723B2 (en) * | 2001-08-30 | 2007-03-06 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
| AU2003234464B2 (en) * | 2002-05-03 | 2009-06-04 | Exelixis, Inc. | Protein kinase modulators and methods of use |
| DE10229070A1 (de) | 2002-06-28 | 2004-01-15 | Merck Patent Gmbh | Phenylderivate 5 |
| UA84146C2 (ru) | 2003-05-21 | 2008-09-25 | Прозидион Лимитед | Амиды пирролопиридин-2-карбоновой кислоты как ингибиторы гликогенфосфорилазы, способ их получения, фармацевтическая композиция и их применение как терапевтических агентов для лечения заболеваний |
| MXPA06001739A (es) | 2003-08-14 | 2006-05-12 | Asahi Kasei Pharma Corp | Derivado de acido arilalcanoico substituido y uso del mismo. |
| MX2007000669A (es) | 2004-07-20 | 2007-05-23 | Siena Biotech Spa | Moduladores de receptores acetilcolina nicotinicos alfa 7 y sus usos terapeuticos. |
| MX2007006790A (es) * | 2004-12-07 | 2007-08-15 | Toyama Chemical Co Ltd | Novedosos derivado de acido antranilico o sal del mismo. |
| KR20070092297A (ko) | 2004-12-21 | 2007-09-12 | 데브젠 엔브이 | Kv4 이온 채널 활성을 갖는 화합물 |
| GT200600042A (es) | 2005-02-10 | 2006-09-27 | Aventis Pharma Inc | Compuestos de bis arilo y heteroarilo sustituido como antagonistas selectivos de 5ht2a |
| US8327467B2 (en) * | 2005-03-16 | 2012-12-11 | Toyama Chemical Co., Ltd. | Anthranilic acid derivative or salt thereof |
| US20060235037A1 (en) * | 2005-04-15 | 2006-10-19 | Purandare Ashok V | Heterocyclic inhibitors of protein arginine methyl transferases |
| WO2007024600A2 (en) | 2005-08-19 | 2007-03-01 | Aventis Pharmaceuticals Inc. | Combination of a hypnotic agent and substituted bis aryl and heteroaryl compound and therapeutic application thereof |
| EP2002834A1 (de) * | 2007-06-13 | 2008-12-17 | Bayer Schering Pharma Aktiengesellschaft | Aryl/Hetarylamide als Modulatoren des EP2-Rezeptors |
| EP2344480A1 (en) | 2008-10-15 | 2011-07-20 | Boehringer Ingelheim International GmbH | Fused heteroaryl diamide compounds useful as mmp-13 inhibitors |
| EP2340243B1 (en) | 2008-10-17 | 2014-10-08 | Boehringer Ingelheim International GmbH | Heteroaryl substituted indole compounds useful as mmp-13 inhibitors |
| JP5584696B2 (ja) | 2008-11-17 | 2014-09-03 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Mmp−13阻害剤として有用なヘテロアリールジアミド化合物 |
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- 2009-10-13 CA CA2738929A patent/CA2738929A1/en not_active Abandoned
- 2009-10-13 US US13/123,048 patent/US8785489B2/en active Active
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| Publication number | Publication date |
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| EP2340243A1 (en) | 2011-07-06 |
| WO2010045188A1 (en) | 2010-04-22 |
| JP2012505891A (ja) | 2012-03-08 |
| CA2738929A1 (en) | 2010-04-22 |
| US8785489B2 (en) | 2014-07-22 |
| EP2340243B1 (en) | 2014-10-08 |
| US20110275631A1 (en) | 2011-11-10 |
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