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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- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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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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- C07D471/00—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
- 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
- C07D471/04—Ortho-condensed systems
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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)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 (enExample) | 2012-11-29 |
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| CA (1) | CA2738929A1 (enExample) |
| WO (1) | WO2010045188A1 (enExample) |
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| WO2010045190A1 (en) | 2008-10-15 | 2010-04-22 | 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 |
| US8637550B2 (en) | 2008-11-17 | 2014-01-28 | Boehringer Ingelheim International Gmbh | Heteroaryl diamide compounds useful as MMP-13 inhibitors |
| BR112012006630A2 (pt) * | 2009-09-24 | 2016-05-03 | Hoffmann La Roche | derivados em indol como moduladores dos canais de cálcio ativados para liberação de cálcio (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 |
| CN103874702B (zh) | 2011-07-15 | 2015-12-09 | 杨森制药公司 | 作为γ分泌酶调节剂的经取代的吲哚衍生物 |
| SG2014012926A (en) * | 2011-08-30 | 2014-06-27 | Chdi Foundation Inc | Kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof |
| US10266490B2 (en) * | 2012-03-16 | 2019-04-23 | Georgetown University | Radioprotector compounds |
| HUE038820T2 (hu) | 2013-11-13 | 2018-11-28 | Vertex Pharma | Eljárás influenzavírusok replikációjának inhibitorai elõállítására |
| US10730866B2 (en) * | 2014-04-07 | 2020-08-04 | Purdue Pharma L.P. | Indole derivatives and use thereof |
| MX372995B (es) | 2014-07-17 | 2020-04-13 | Chdi Foundation Inc | Metodos y composiciones para el tratamiento de trastornos relacionados con vih. |
| WO2016026078A1 (en) * | 2014-08-19 | 2016-02-25 | Changzhou Jiekai Pharmatech Co., Ltd. | Heterocyclic compounds as erk inhibitors |
| US9938273B2 (en) | 2015-12-07 | 2018-04-10 | Plexxikon Inc. | Compounds and methods for kinase modulation, and indications therefor |
| 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 |
| 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 |
| ES2902504T3 (es) | 2016-09-09 | 2022-03-28 | Bristol Myers Squibb Co | Compuestos de indol sustituidos con piridilo |
| WO2018226846A1 (en) | 2017-06-07 | 2018-12-13 | Plexxikon Inc. | Compounds and methods for kinase modulation |
| EP3661926B1 (en) | 2017-08-04 | 2022-02-23 | Bristol-Myers Squibb Company | Substituted indole compounds useful as inhibitors of 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 |
| CN111448190B (zh) | 2017-11-14 | 2023-09-26 | 百时美施贵宝公司 | 取代的吲哚化合物 |
| US12030878B2 (en) | 2017-12-15 | 2024-07-09 | Bristol-Myers Squibb Company | Substituted indole ether compounds |
| MX2020006168A (es) | 2017-12-18 | 2020-08-13 | Bristol Myers Squibb Co | Compuestos de 4-azaindol. |
| WO2019126081A1 (en) | 2017-12-19 | 2019-06-27 | Bristol-Myers Squibb Company | Amide substituted indole compounds useful as tlr inhibitors |
| EA202091474A1 (ru) | 2017-12-19 | 2020-11-18 | Бристол-Маерс Сквибб Компани | Замещенные индольные соединения, применимые в качестве ингибиторов tlr |
| EP3728253B1 (en) | 2017-12-19 | 2024-03-27 | Bristol-Myers Squibb Company | 6-azaindole compounds |
| JP7287967B2 (ja) | 2017-12-20 | 2023-06-06 | ブリストル-マイヤーズ スクイブ カンパニー | Tlr阻害剤として有効なアミノインドール化合物 |
| KR102730859B1 (ko) | 2017-12-20 | 2024-11-15 | 브리스톨-마이어스 스큅 컴퍼니 | 아릴 및 헤테로아릴 치환된 인돌 화합물 |
| EA202091530A1 (ru) | 2017-12-20 | 2020-09-14 | Бристол-Маерс Сквибб Компани | Диазаиндольные соединения |
| JP7478142B2 (ja) | 2018-06-07 | 2024-05-02 | ディスアーム セラピューティクス, インコーポレイテッド | Sarm1阻害剤 |
| EP3628669A1 (en) * | 2018-09-28 | 2020-04-01 | GenKyoTex Suisse SA | Novel compounds as nadph oxidase inhibitors |
| ES2963696T3 (es) | 2018-10-24 | 2024-04-01 | Bristol Myers Squibb Co | Compuestos diméricos de indol sustituidos |
| US12172995B2 (en) | 2018-10-24 | 2024-12-24 | Bristol-Myers Squibb Company | Substituted indole and indazole compounds |
| CA3123215C (en) | 2018-12-19 | 2024-04-02 | Disarm Therapeutics, Inc. | Inhibitors of sarm1 in combination with neuroprotective agents |
| KR102904576B1 (ko) | 2019-05-09 | 2025-12-24 | 브리스톨-마이어스 스큅 컴퍼니 | 치환된 벤즈이미다졸론 화합물 |
| WO2021067326A1 (en) | 2019-10-01 | 2021-04-08 | Bristol-Myers Squibb Company | Substituted bicyclic heteroaryl compounds |
| CN114829350B (zh) | 2019-10-04 | 2024-05-28 | 百时美施贵宝公司 | 经取代的咔唑化合物 |
| 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 |
| 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 |
| WO2022040267A1 (en) | 2020-08-19 | 2022-02-24 | 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 |
| 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 |
| US20260092058A1 (en) | 2024-09-30 | 2026-04-02 | St. Jude Children's Research Hospital, Inc. | Small Molecule Degraders and Fluorescent Probes of PXR |
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| JPH08151380A (ja) * | 1994-11-29 | 1996-06-11 | Kyorin Pharmaceut Co Ltd | ビス(トリフルオロメチルピロロインドールカルボン酸エステル)誘導体及びその製造方法 |
| AU2164300A (en) | 1998-12-04 | 2000-06-26 | N.V. Organon | Substituted thiazoles for treatment of human diseases involving modulators of p-, l- and e- selectin |
| HUP0302966A2 (hu) | 2000-07-31 | 2003-12-29 | Smithkline Beecham P.L.C. | Karboxamid-vegyületek és alkalmazásuk humán 11CBY receptor antagonistákként, eljárás az előállításukra és ezeket tartalmazó gyógyszerkészítmények |
| 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 |
| WO2003020699A2 (en) * | 2001-08-30 | 2003-03-13 | 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 |
| EP1636224B1 (en) | 2003-05-21 | 2010-07-14 | Prosidion Limited | Pyrrolopyridine-2-carboxylic acid amide inhibitors of glycogen phoshorylase |
| KR20060079190A (ko) | 2003-08-14 | 2006-07-05 | 아사히 가세이 파마 가부시키가이샤 | 치환 아릴알칸산 유도체 및 그의 용도 |
| US20080275028A1 (en) | 2004-07-20 | 2008-11-06 | Giovanni Gaviraghi | Modulators or Alpha7 Nicotinic Acetylcholine Receptors and Therapeutic Uses Thereof |
| EP1820795A4 (en) * | 2004-12-07 | 2010-10-20 | Toyama Chemical Co Ltd | NEW ANTHRANILIC ACID DERIVATIVE OR SALT FROM IT |
| EP1838690A2 (en) | 2004-12-21 | 2007-10-03 | Devgen N.V. | Compounds with kv4 ion channel activity |
| GT200600042A (es) | 2005-02-10 | 2006-09-27 | Aventis Pharma Inc | Compuestos de bis arilo y heteroarilo sustituido como antagonistas selectivos de 5ht2a |
| EP1860098B1 (en) * | 2005-03-16 | 2012-11-14 | Toyama Chemical Co., Ltd. | Novel anthranilic acid derivative or salt thereof |
| US20060235037A1 (en) * | 2005-04-15 | 2006-10-19 | Purandare Ashok V | Heterocyclic inhibitors of protein arginine methyl transferases |
| MX2008001778A (es) | 2005-08-19 | 2008-04-07 | Aventis Pharma Inc | Combinacion de un agente hipnotico y un compuesto de bis arilo y heteroarilo sustituido y aplicacion terapeutica de la misma. |
| EP2002834A1 (de) * | 2007-06-13 | 2008-12-17 | Bayer Schering Pharma Aktiengesellschaft | Aryl/Hetarylamide als Modulatoren des EP2-Rezeptors |
| WO2010045190A1 (en) | 2008-10-15 | 2010-04-22 | 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 |
| US8637550B2 (en) | 2008-11-17 | 2014-01-28 | Boehringer Ingelheim International Gmbh | Heteroaryl diamide compounds useful as MMP-13 inhibitors |
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- 2009-10-13 WO PCT/US2009/060436 patent/WO2010045188A1/en not_active Ceased
- 2009-10-13 US US13/123,048 patent/US8785489B2/en active Active
- 2009-10-13 JP JP2011532175A patent/JP5529876B2/ja not_active Expired - Fee Related
- 2009-10-13 CA CA2738929A patent/CA2738929A1/en not_active Abandoned
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| Publication number | Publication date |
|---|---|
| US20110275631A1 (en) | 2011-11-10 |
| EP2340243B1 (en) | 2014-10-08 |
| JP2012505891A (ja) | 2012-03-08 |
| EP2340243A1 (en) | 2011-07-06 |
| CA2738929A1 (en) | 2010-04-22 |
| US8785489B2 (en) | 2014-07-22 |
| WO2010045188A1 (en) | 2010-04-22 |
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