CA2741428C - Azaindole derivatives - Google Patents
Azaindole derivatives Download PDFInfo
- Publication number
- CA2741428C CA2741428C CA2741428A CA2741428A CA2741428C CA 2741428 C CA2741428 C CA 2741428C CA 2741428 A CA2741428 A CA 2741428A CA 2741428 A CA2741428 A CA 2741428A CA 2741428 C CA2741428 C CA 2741428C
- Authority
- CA
- Canada
- Prior art keywords
- pyrrolo
- pyridine
- carbonitrile
- stereoisomers
- 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.)
- Expired - Fee Related
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- 125000005334 azaindolyl group Chemical class N1N=C(C2=CC=CC=C12)* 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 171
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 50
- 150000003839 salts Chemical class 0.000 claims description 101
- 239000000203 mixture Substances 0.000 claims description 91
- 238000011282 treatment Methods 0.000 claims description 40
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 35
- 201000010099 disease Diseases 0.000 claims description 33
- 239000003814 drug Substances 0.000 claims description 33
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- 238000002360 preparation method Methods 0.000 claims description 19
- 206010012689 Diabetic retinopathy Diseases 0.000 claims description 6
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- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
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- 208000026310 Breast neoplasm Diseases 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 5
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- TUAAFDBIJNTBKW-UHFFFAOYSA-N 2-(2-chloropyridin-4-yl)-3-(4-fluorophenyl)-1h-pyrrolo[3,2-b]pyridine-5-carbonitrile Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=C(Cl)N=CC=2)NC2=CC=C(C#N)N=C12 TUAAFDBIJNTBKW-UHFFFAOYSA-N 0.000 claims 2
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- PQCPYSVTVBSQJY-UHFFFAOYSA-N 2-(2-aminopyridin-4-yl)-3-(3-chloro-4-fluorophenyl)-1h-pyrrolo[3,2-b]pyridine-5-carbonitrile Chemical compound C1=NC(N)=CC(C2=C(C3=NC(=CC=C3N2)C#N)C=2C=C(Cl)C(F)=CC=2)=C1 PQCPYSVTVBSQJY-UHFFFAOYSA-N 0.000 claims 1
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- FCEAJLIPRKASSF-UHFFFAOYSA-N 2-(6-aminopyridin-3-yl)-3-(3-chloro-4-fluorophenyl)-1h-pyrrolo[3,2-b]pyridine-5-carbonitrile Chemical compound C1=NC(N)=CC=C1C1=C(C=2C=C(Cl)C(F)=CC=2)C2=NC(C#N)=CC=C2N1 FCEAJLIPRKASSF-UHFFFAOYSA-N 0.000 claims 1
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- NMARHRXJOFFAMY-UHFFFAOYSA-N 2-[2-(benzylamino)pyridin-4-yl]-3-(3-chloro-4-fluorophenyl)-1h-pyrrolo[3,2-b]pyridine-5-carbonitrile Chemical compound C1=C(Cl)C(F)=CC=C1C1=C(C=2C=C(NCC=3C=CC=CC=3)N=CC=2)NC2=CC=C(C#N)N=C12 NMARHRXJOFFAMY-UHFFFAOYSA-N 0.000 claims 1
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- IPQQKDAYBQMYIE-UHFFFAOYSA-N 3-(2-aminopyrimidin-5-yl)-2-pyridin-4-yl-1h-pyrrolo[3,2-b]pyridine-5-carbonitrile Chemical compound C1=NC(N)=NC=C1C1=C(C=2C=CN=CC=2)NC2=CC=C(C#N)N=C12 IPQQKDAYBQMYIE-UHFFFAOYSA-N 0.000 claims 1
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- AVAWJZQFPDDPSF-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-2-pyridin-4-yl-1h-pyrrolo[3,2-b]pyridine-5-carbonitrile Chemical compound C1=C(Cl)C(Cl)=CC=C1C1=C(C=2C=CN=CC=2)NC2=CC=C(C#N)N=C12 AVAWJZQFPDDPSF-UHFFFAOYSA-N 0.000 claims 1
- XSWFPAQEENJOFK-UHFFFAOYSA-N 3-(3,4-difluorophenyl)-2-pyridin-4-yl-1h-pyrrolo[3,2-b]pyridine-5-carbonitrile Chemical compound C1=C(F)C(F)=CC=C1C1=C(C=2C=CN=CC=2)NC2=CC=C(C#N)N=C12 XSWFPAQEENJOFK-UHFFFAOYSA-N 0.000 claims 1
- AJTIEFRBXKZDMY-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-2-pyridin-4-yl-1h-pyrrolo[3,2-b]pyridine-5-carbonitrile Chemical compound ClC1=CC(Cl)=CC(C=2C3=NC(=CC=C3NC=2C=2C=CN=CC=2)C#N)=C1 AJTIEFRBXKZDMY-UHFFFAOYSA-N 0.000 claims 1
- ZPWJDPSQBLIDQE-UHFFFAOYSA-N 3-(3,5-dimethyl-1,2-oxazol-4-yl)-2-pyridin-4-yl-1h-pyrrolo[3,2-b]pyridine-5-carbonitrile Chemical compound CC1=NOC(C)=C1C1=C(C=2C=CN=CC=2)NC2=CC=C(C#N)N=C12 ZPWJDPSQBLIDQE-UHFFFAOYSA-N 0.000 claims 1
- FGZGNQMSLQEFKI-UHFFFAOYSA-N 3-(3-chloro-4-fluorophenyl)-2-(1h-pyrrolo[2,3-b]pyridin-5-yl)-1h-pyrrolo[3,2-b]pyridine-5-carbonitrile Chemical compound C1=C(Cl)C(F)=CC=C1C1=C(C=2C=C3C=CNC3=NC=2)NC2=CC=C(C#N)N=C12 FGZGNQMSLQEFKI-UHFFFAOYSA-N 0.000 claims 1
- VZTBOCWTRFEYTA-UHFFFAOYSA-N 3-(3-chloro-4-fluorophenyl)-2-pyridin-4-yl-1h-pyrrolo[3,2-b]pyridine-5-carbonitrile Chemical compound C1=C(Cl)C(F)=CC=C1C1=C(C=2C=CN=CC=2)NC2=CC=C(C#N)N=C12 VZTBOCWTRFEYTA-UHFFFAOYSA-N 0.000 claims 1
- ACJHDNQLSVYCSQ-UHFFFAOYSA-N 3-(3-chloro-4-fluorophenyl)-2-pyrimidin-5-yl-1h-pyrrolo[3,2-b]pyridine-5-carbonitrile Chemical compound C1=C(Cl)C(F)=CC=C1C1=C(C=2C=NC=NC=2)NC2=CC=C(C#N)N=C12 ACJHDNQLSVYCSQ-UHFFFAOYSA-N 0.000 claims 1
- JQNWYOYBMABACN-UHFFFAOYSA-N 3-(3-chloro-5-fluorophenyl)-2-pyridin-4-yl-1h-pyrrolo[3,2-b]pyridine-5-carbonitrile Chemical compound FC1=CC(Cl)=CC(C=2C3=NC(=CC=C3NC=2C=2C=CN=CC=2)C#N)=C1 JQNWYOYBMABACN-UHFFFAOYSA-N 0.000 claims 1
- UNXXKODFVOTBFX-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-pyridin-4-yl-1h-pyrrolo[3,2-b]pyridine-5-carbonitrile Chemical compound ClC1=CC=CC(C=2C3=NC(=CC=C3NC=2C=2C=CN=CC=2)C#N)=C1 UNXXKODFVOTBFX-UHFFFAOYSA-N 0.000 claims 1
- CECZSDHXYCMWDB-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-pyridin-4-yl-1h-pyrrolo[3,2-b]pyridine-5-carboxamide Chemical compound C12=NC(C(=O)N)=CC=C2NC(C=2C=CN=CC=2)=C1C1=CC=CC(Cl)=C1 CECZSDHXYCMWDB-UHFFFAOYSA-N 0.000 claims 1
- BTTYYIDCEBEYKZ-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-pyridin-4-yl-1h-pyrrolo[3,2-b]pyridine-5-carboxylic acid Chemical compound C12=NC(C(=O)O)=CC=C2NC(C=2C=CN=CC=2)=C1C1=CC=CC(Cl)=C1 BTTYYIDCEBEYKZ-UHFFFAOYSA-N 0.000 claims 1
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- XMQCERYIIOBWNE-UHFFFAOYSA-N 3-(3-chlorophenyl)-n-(2-morpholin-4-ylethyl)-2-pyridin-4-yl-1h-pyrrolo[3,2-b]pyridine-5-carboxamide Chemical compound ClC1=CC=CC(C=2C3=NC(=CC=C3NC=2C=2C=CN=CC=2)C(=O)NCCN2CCOCC2)=C1 XMQCERYIIOBWNE-UHFFFAOYSA-N 0.000 claims 1
- OOOKSDQKLLKRAO-UHFFFAOYSA-N 3-(3-fluorophenyl)-2-pyridin-4-yl-1h-pyrrolo[3,2-b]pyridine-5-carbonitrile Chemical compound FC1=CC=CC(C=2C3=NC(=CC=C3NC=2C=2C=CN=CC=2)C#N)=C1 OOOKSDQKLLKRAO-UHFFFAOYSA-N 0.000 claims 1
- OXTHCEQMNCQZDC-UHFFFAOYSA-N 3-(4-bromophenyl)-2-pyridin-4-yl-1h-pyrrolo[3,2-b]pyridine-5-carbonitrile Chemical compound C1=CC(Br)=CC=C1C1=C(C=2C=CN=CC=2)NC2=CC=C(C#N)N=C12 OXTHCEQMNCQZDC-UHFFFAOYSA-N 0.000 claims 1
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- A—HUMAN NECESSITIES
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
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- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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| DE102008052943A DE102008052943A1 (de) | 2008-10-23 | 2008-10-23 | Azaindolderivate |
| PCT/EP2009/006911 WO2010046013A1 (de) | 2008-10-23 | 2009-09-24 | Azaindolderivate |
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| JP5596364B2 (ja) * | 2009-02-19 | 2014-09-24 | 住友化学株式会社 | 含窒素有機化合物及びそれを用いた有機エレクトロルミネッセンス素子 |
| WO2011075613A1 (en) * | 2009-12-18 | 2011-06-23 | Sanofi | Azaindole derivatives, their preparation and their therapeutic application |
| DE102010050558A1 (de) * | 2010-11-05 | 2012-05-10 | Merck Patent Gmbh | 1H-Pyrrolo[2,3-b]pyridinderivate |
| JP5902293B2 (ja) | 2011-04-25 | 2016-04-13 | アッシャー・サード・イニシアティブ・インコーポレイテッド | ピラゾロピリダジンおよび網膜変性疾患およびアッシャー症候群に伴う聴覚損失を治療するための方法 |
| KR101913619B1 (ko) | 2011-06-09 | 2018-12-28 | 리젠 파마슈티컬스 소시에떼 아노님 | Gpr-119의 조절제로서의 신규한 화합물 |
| GB201217285D0 (en) * | 2012-09-27 | 2012-11-14 | Univ Central Lancashire | Indole derivatives |
| US9227976B2 (en) | 2012-10-25 | 2016-01-05 | Usher Iii Initiative, Inc. | Pyrazolopyridazines and methods for treating retinal-degenerative diseases and hearing loss associated with usher syndrome |
| JP6320506B2 (ja) * | 2013-03-12 | 2018-05-09 | セルジーン クオンティセル リサーチ，インク． | ヒストンデメチラーゼ阻害剤 |
| EP3096761A1 (en) * | 2014-01-24 | 2016-11-30 | Confluence Life Sciences, Inc. | Substituted pyroolopyridines and pyrrolopyrazines for treating cancer or inflammatory diseases |
| EA201650031A1 (ru) | 2014-05-15 | 2017-06-30 | Итеос Терапьютик | Производные пирролидин-2,5-диона, фармацевтические композиции и способы применения в качестве ингибиторов ido1 |
| AR103232A1 (es) * | 2014-12-22 | 2017-04-26 | Bristol Myers Squibb Co | ANTAGONISTAS DE TGFbR |
| AU2016209046A1 (en) | 2015-01-23 | 2017-07-20 | Aclaris Therapeutics, Inc. | Heterocyclic ITK inhibitors for treating inflammation and cancer |
| BR112017019699A2 (pt) | 2015-03-17 | 2018-09-04 | Pfizer Inc. | derivados substituídos por 3-indol, composições farmacêuticas e métodos para uso |
| US10544095B2 (en) | 2015-08-10 | 2020-01-28 | Pfizer Inc. | 3-indol substituted derivatives, pharmaceutical compositions and methods for use |
| WO2017149463A1 (en) * | 2016-03-01 | 2017-09-08 | Novartis Ag | Cyano-substituted indole compounds and uses thereof as lsd1 inhibitors |
| CN109311858B (zh) * | 2016-05-26 | 2021-12-03 | 里科瑞尔姆Ip控股有限责任公司 | Egfr抑制剂化合物 |
| WO2018059549A1 (en) * | 2016-09-30 | 2018-04-05 | Novartis Ag | Immune effector cell therapies with enhanced efficacy |
| WO2018210660A1 (en) | 2017-05-15 | 2018-11-22 | Basf Se | Heteroaryl compounds as agrochemical fungicides |
| WO2018210659A1 (en) | 2017-05-15 | 2018-11-22 | Basf Se | Heteroaryl compounds as agrochemical fungicides |
| WO2018210661A1 (en) | 2017-05-15 | 2018-11-22 | Basf Se | Heteroaryl compounds as agrochemical fungicides |
| WO2018210658A1 (en) | 2017-05-15 | 2018-11-22 | Basf Se | Heteroaryl compounds as agrochemical fungicides |
| WO2019057660A1 (en) | 2017-09-25 | 2019-03-28 | Basf Se | INDOLE AND AZAINDOLE COMPOUNDS HAVING 6-CHANNEL SUBSTITUTED ARYL AND HETEROARYL CYCLES AS AGROCHEMICAL FUNGICIDES |
| EP3730489A1 (en) | 2019-04-25 | 2020-10-28 | Basf Se | Heteroaryl compounds as agrochemical fungicides |
| EP4178580B1 (en) | 2020-07-09 | 2025-11-05 | Usher III Initiative, Inc. | Bf 844 for use in the treatment of cancer |
| KR102513463B1 (ko) * | 2020-11-26 | 2023-03-29 | 주식회사 에스앤케이테라퓨틱스 | 엔도솜 톨-유사 수용체를 제어하는 신규 소분자 화합물 및 이를 이용한 자가면역질환 치료제 |
| CA3231948A1 (en) * | 2021-09-23 | 2023-03-30 | Jingyu Hu | Fgfr inhibitors and methods of use thereof |
| CN116332940B (zh) * | 2023-02-14 | 2024-09-13 | 广西民族大学 | 一种7-脱氮嘌呤衍生物及其制备方法和应用 |
| WO2024245193A1 (zh) * | 2023-05-26 | 2024-12-05 | 上海艾力斯医药科技股份有限公司 | 杂芳环类化合物、其药物组合物及其应用 |
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| CA2242425C (en) | 1996-02-13 | 2006-07-18 | Zeneca Limited | Quinazoline derivatives as vegf inhibitors |
| NZ331191A (en) | 1996-03-05 | 2000-03-27 | Zeneca Ltd | 4-anilinoquinazoline derivatives and pharmaceutical compositions thereof |
| GB9718972D0 (en) | 1996-09-25 | 1997-11-12 | Zeneca Ltd | Chemical compounds |
| HUP9903330A2 (hu) * | 1996-11-19 | 2000-03-28 | Amgen Inc. | Gyulladásgátló hatású, aril- és heteroaril csoporttal szubsztituált kondenzált pirrolszármazékok, valamint ezeket tartalmazó gyógyászati készítmények |
| GB9714249D0 (en) | 1997-07-08 | 1997-09-10 | Angiogene Pharm Ltd | Vascular damaging agents |
| HRP20000209A2 (en) | 1997-10-20 | 2001-04-30 | Hoffmann La Roche | Bicyclic kinase inhibitors |
| US6187777B1 (en) * | 1998-02-06 | 2001-02-13 | Amgen Inc. | Compounds and methods which modulate feeding behavior and related diseases |
| GB9900334D0 (en) | 1999-01-07 | 1999-02-24 | Angiogene Pharm Ltd | Tricylic vascular damaging agents |
| GB9900752D0 (en) | 1999-01-15 | 1999-03-03 | Angiogene Pharm Ltd | Benzimidazole vascular damaging agents |
| DE19951360A1 (de) * | 1999-10-26 | 2001-05-03 | Aventis Pharma Gmbh | Substituierte Indole |
| JP2001122855A (ja) * | 1999-10-27 | 2001-05-08 | Japan Tobacco Inc | インドール化合物及びその医薬用途 |
| BR0111230A (pt) | 2000-05-31 | 2003-06-10 | Astrazeneca Ab | Composto, e, uso e processo para a preparação do mesmo |
| EE200300015A (et) | 2000-07-07 | 2004-10-15 | Angiogene Pharmaceuticals Limited | Kolhinooli derivaadid kui angiogeneesi inhibiitorid |
| KR20030014425A (ko) | 2000-07-07 | 2003-02-17 | 앤지오젠 파마슈티칼스 리미티드 | 혈관 손상제인 콜치놀 유도체 |
| AUPR283801A0 (en) * | 2001-02-01 | 2001-03-01 | Australian National University, The | Chemical compounds and methods |
| SE0202463D0 (sv) | 2002-08-14 | 2002-08-14 | Astrazeneca Ab | Novel compounds |
| WO2004032874A2 (en) | 2002-10-09 | 2004-04-22 | Scios Inc. | AZAINDOLE DERIVATIVES AS INHIBITORS OF p38 KINASE |
| US7432375B2 (en) | 2003-03-06 | 2008-10-07 | Eisai R & D Management Co., Ltd. | JNK inhibitors |
| JP5138938B2 (ja) | 2003-12-19 | 2013-02-06 | プレキシコン インコーポレーテッド | Ｒｅｔ調節剤の開発のための化合物および方法 |
| GB0405055D0 (en) | 2004-03-05 | 2004-04-07 | Eisai London Res Lab Ltd | JNK inhibitors |
| ES2364340T3 (es) * | 2004-03-30 | 2011-08-31 | Vertex Pharmaceuticals Incorporated | Azaindoles útiles como inhibidores de jak y otras proteína quinasas. |
| EP2325184A1 (en) | 2004-06-30 | 2011-05-25 | Vertex Pharmceuticals Incorporated | Azaindoles useful as inhibitors of protein kinases |
| MX2007001399A (es) | 2004-08-02 | 2007-04-18 | Osi Pharm Inc | Compuestos que inhiben pirrolopirimidina multi-cinasa aril-amino sustituidas. |
| WO2006112828A1 (en) | 2005-04-15 | 2006-10-26 | Scios, Inc. | Azaindole derivatives as inhibitors of p38 kinase |
| FR2884821B1 (fr) | 2005-04-26 | 2007-07-06 | Aventis Pharma Sa | Pyrrolopyridines substitues, compositions les contenant, procede de fabrication et utilisation |
| JP2008545660A (ja) | 2005-05-20 | 2008-12-18 | バーテックス ファーマシューティカルズ インコーポレイテッド | プロテインキナーゼ阻害剤として有用なピロロピリジン化合物 |
| MY153898A (en) | 2005-06-22 | 2015-04-15 | Plexxikon Inc | Compounds and methods for kinase modulation, and indications therefor |
| CN102127078A (zh) | 2005-07-14 | 2011-07-20 | 安斯泰来制药株式会社 | Janus激酶3的杂环类抑制剂 |
| JP5071374B2 (ja) | 2005-07-14 | 2012-11-14 | アステラス製薬株式会社 | ヘテロ環ヤヌスキナーゼ３阻害剤 |
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| WO2007067537A1 (en) | 2005-12-07 | 2007-06-14 | Osi Pharmaceuticals, Inc. | Pyrrolopyridine kinase inhibiting compounds |
| EP1962851A2 (en) | 2005-12-22 | 2008-09-03 | SmithKline Beecham Corporation | Compounds |
| WO2007076348A2 (en) | 2005-12-23 | 2007-07-05 | Smithkline Beecham Corporation | Azaindole inhibitors of aurora kinases |
| WO2007135398A1 (en) | 2006-05-22 | 2007-11-29 | Astrazeneca Ab | Indole derivatives |
| WO2008014249A2 (en) | 2006-07-24 | 2008-01-31 | Sanofi-Aventis | Improved preparations of 2 -substituted pyrrolo [2, 3-b] pyrazine ( 4, 7 -diazaindole ) compounds |
| GB0708141D0 (en) * | 2007-04-26 | 2007-06-06 | Syngenta Participations Ag | Improvements in or relating to organic compounds |
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| WO2010046013A1 (de) | 2010-04-29 |
| CA2741428A1 (en) | 2010-04-29 |
| ES2559427T3 (es) | 2016-02-12 |
| JP5662325B2 (ja) | 2015-01-28 |
| AU2009306795A1 (en) | 2010-04-29 |
| IL212285A0 (en) | 2011-06-30 |
| EP2342202A1 (de) | 2011-07-13 |
| AU2009306795B2 (en) | 2015-07-16 |
| JP2012506389A (ja) | 2012-03-15 |
| DE102008052943A1 (de) | 2010-04-29 |
| EP2342202B1 (de) | 2015-11-11 |
| US20110207732A1 (en) | 2011-08-25 |
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