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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- A61P37/02—Immunomodulators
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
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- A—HUMAN NECESSITIES
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- A61P9/00—Drugs for disorders of the cardiovascular system
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D209/10—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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- Endocrinology (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102008052943.5 | 2008-10-23 | ||
| 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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| CA2741428A1 CA2741428A1 (en) | 2010-04-29 |
| CA2741428C true CA2741428C (en) | 2017-05-09 |
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| EP (1) | EP2342202B1 (enExample) |
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| IL (1) | IL212285A0 (enExample) |
| WO (1) | WO2010046013A1 (enExample) |
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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 |
| EP2701510B1 (en) | 2011-04-25 | 2017-02-15 | Usher III Initiative | Pyrazolopyridazines and methods for treating retinal-degenerative diseases and hearing loss associated with usher syndrome |
| WO2012170867A1 (en) * | 2011-06-09 | 2012-12-13 | Rhizen Pharmaceuticals Sa | Novel compounds as modulators of gpr-119 |
| 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 |
| WO2014164708A1 (en) * | 2013-03-12 | 2014-10-09 | Quanticel Pharmaceuticals, Inc. | Histone dementhylase inhibitors |
| JP2017503815A (ja) * | 2014-01-24 | 2017-02-02 | コンフルエンス・ライフ・サイエンシズ，インコーポレーテッド | がんまたは炎症性疾患を処置するための置換されたピロロピリジンおよびピロロピラジン |
| MD20160118A2 (ro) | 2014-05-15 | 2017-04-30 | Iteos Therapeutics | Derivaţi ai pirolidin-2,5-dionei, compoziţii farmaceutice şi metode de utilizare ca inhibitori ai IDO1 |
| AR103232A1 (es) | 2014-12-22 | 2017-04-26 | Bristol Myers Squibb Co | ANTAGONISTAS DE TGFbR |
| HK1245677A1 (zh) | 2015-01-23 | 2018-08-31 | Aclaris Therapeutics, Inc. | 用於治疗炎症和癌症的杂环itk抑制剂 |
| EP3271354A1 (en) | 2015-03-17 | 2018-01-24 | Pfizer Inc | Novel 3-indol substituted derivatives, pharmaceutical compositions and methods for use |
| EP3334733A1 (en) | 2015-08-10 | 2018-06-20 | 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 |
| SG11201809751XA (en) * | 2016-05-26 | 2018-12-28 | Zeno Royalties & Milestones Llc | Egfr inhibitor compounds |
| CN110582488A (zh) * | 2016-09-30 | 2019-12-17 | 诺华股份有限公司 | 具有增强功效的免疫效应细胞疗法 |
| WO2018210658A1 (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 |
| 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 |
| 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 |
| KR102513463B1 (ko) | 2020-11-26 | 2023-03-29 | 주식회사 에스앤케이테라퓨틱스 | 엔도솜 톨-유사 수용체를 제어하는 신규 소분자 화합물 및 이를 이용한 자가면역질환 치료제 |
| 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 |
| CN121263414A (zh) * | 2023-05-26 | 2026-01-02 | 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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| US3009A (en) * | 1843-03-21 | Lard-lamp | ||
| US7004A (en) * | 1850-01-08 | Connecting ctjttees to shafts of boeing instetjments | ||
| US3022A (en) * | 1843-03-30 | Machine for bending stibrups for paddle-wheels of steam and other | ||
| GB9624482D0 (en) | 1995-12-18 | 1997-01-15 | Zeneca Phaema S A | Chemical compounds |
| IL125686A (en) | 1996-02-13 | 2002-11-10 | Zeneca Ltd | Quinazoline derivatives, processes for their preparation, pharmaceutical preparations containing them and their use in the manufacture of a drug with an anti-angiogenic effect and / or an effect of reducing vascular permeability |
| IL125954A (en) | 1996-03-05 | 2003-06-24 | Zeneca Ltd | Quinazoline derivatives, processes for their preparation, pharmaceutical compositions containing them and use thereof in the manufacture of medicaments having an antiangiogenic and/or vascular permeability reducing effect |
| 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 |
| CN1279682A (zh) | 1997-10-20 | 2001-01-10 | 霍夫曼-拉罗奇有限公司 | 双环激酶抑制剂 |
| 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 |
| JP2003535078A (ja) | 2000-05-31 | 2003-11-25 | アストラゼネカ アクチボラグ | 血管損傷活性のあるインドール誘導体 |
| CA2411160A1 (en) | 2000-07-07 | 2002-01-17 | Angiogene Pharmaceuticals Limited | Colchinol derivatives as vascular damaging agents |
| RU2003103603A (ru) | 2000-07-07 | 2004-08-20 | Энджиоджен Фармасьютикалз Лимитед (Gb) | Производные колхинола в качестве ингибиторов ангиогенеза |
| 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 |
| NZ539390A (en) | 2002-10-09 | 2007-05-31 | Scios Inc | Azaindole derivatives as inhibitors of p38 kinase |
| EP1599475A2 (en) | 2003-03-06 | 2005-11-30 | Eisai Co., Ltd. | Jnk inhibitors |
| WO2005062795A2 (en) | 2003-12-19 | 2005-07-14 | Plexxikon, Inc. | Compounds and methods for development of ret modulators |
| GB0405055D0 (en) | 2004-03-05 | 2004-04-07 | Eisai London Res Lab Ltd | JNK inhibitors |
| EP1730146B1 (en) * | 2004-03-30 | 2011-05-04 | Vertex Pharmaceuticals Incorporated | Azaindoles useful as inhibitors of jak and other protein kinases |
| CA2572058A1 (en) | 2004-06-30 | 2006-01-12 | Vertex Pharmaceuticals Incorporated | Azaindoles useful as inhibitors of protein kinases |
| CA2575808A1 (en) | 2004-08-02 | 2006-02-16 | Osi Pharmaceuticals, Inc. | Aryl-amino substituted pyrrolopyrimidine multi-kinase inhibiting compounds |
| 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 |
| EP2354139A1 (en) | 2005-05-20 | 2011-08-10 | Vertex Pharmaceuticals Incorporated | Pyrrolopyridines useful as inhibitors of protein kinase |
| NZ565255A (en) | 2005-06-22 | 2010-04-30 | Plexxikon Inc | Pyrrolo[2,3-b] pyridine derivatives as protein kinase inhibitors |
| CA2615291A1 (en) | 2005-07-14 | 2007-01-18 | Astellas Pharma Inc. | Heterocyclic janus kinase 3 inhibitors |
| EP2251341A1 (en) | 2005-07-14 | 2010-11-17 | Astellas Pharma Inc. | Heterocyclic Janus kinase 3 inhibitors |
| US8119655B2 (en) | 2005-10-07 | 2012-02-21 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
| JP2009531274A (ja) | 2005-12-07 | 2009-09-03 | オーエスアイ・ファーマスーティカルズ・インコーポレーテッド | キナーゼ阻害性ピロロピリジン化合物 |
| WO2007076320A2 (en) | 2005-12-22 | 2007-07-05 | Smithkline Beecham Corporation | Compounds |
| JP5140600B2 (ja) | 2005-12-23 | 2013-02-06 | グラクソスミスクライン・リミテッド・ライアビリティ・カンパニー | オーロラキナーゼのアザインドール阻害薬 |
| EP2029593A1 (en) | 2006-05-22 | 2009-03-04 | 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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2011
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| IL212285A0 (en) | 2011-06-30 |
| ES2559427T3 (es) | 2016-02-12 |
| AU2009306795A1 (en) | 2010-04-29 |
| US20110207732A1 (en) | 2011-08-25 |
| EP2342202B1 (de) | 2015-11-11 |
| EP2342202A1 (de) | 2011-07-13 |
| DE102008052943A1 (de) | 2010-04-29 |
| JP2012506389A (ja) | 2012-03-15 |
| AU2009306795B2 (en) | 2015-07-16 |
| JP5662325B2 (ja) | 2015-01-28 |
| CA2741428A1 (en) | 2010-04-29 |
| WO2010046013A1 (de) | 2010-04-29 |
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