AU2007338754A1 - 5-cyan0-4- (pyrrolo [2, 3B] pyridine-3-yl) -pyrimidine derivatives useful as protein kinase inhibitors - Google Patents
5-cyan0-4- (pyrrolo [2, 3B] pyridine-3-yl) -pyrimidine derivatives useful as protein kinase inhibitors Download PDFInfo
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- AU2007338754A1 AU2007338754A1 AU2007338754A AU2007338754A AU2007338754A1 AU 2007338754 A1 AU2007338754 A1 AU 2007338754A1 AU 2007338754 A AU2007338754 A AU 2007338754A AU 2007338754 A AU2007338754 A AU 2007338754A AU 2007338754 A1 AU2007338754 A1 AU 2007338754A1
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- compound
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- alkyl
- independently
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| CN103110948A (zh) | 2005-11-04 | 2013-05-22 | 惠氏公司 | mTOR抑制剂、赫赛汀和/或HKI-272的抗肿瘤组合 |
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| CN101778825A (zh) * | 2007-03-22 | 2010-07-14 | 沃泰克斯药物股份有限公司 | 适用作詹纳斯激酶抑制剂的n-杂环类化合物 |
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| WO2010008744A2 (en) | 2008-06-17 | 2010-01-21 | Wyeth | Antineoplastic combinations containing hki-272 and vinorelbine |
| RU2498804C2 (ru) | 2008-08-04 | 2013-11-20 | ВАЙЕТ ЭлЭлСи | Противоопухолевые комбинации из 4-анилино-3-цианохинолинов и капецитабина |
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| JP5992325B2 (ja) | 2009-04-06 | 2016-09-14 | ワイス・エルエルシー | 乳癌のための、ネラチニブを活用する治療計画 |
| NZ596123A (en) * | 2009-05-19 | 2014-08-29 | Dow Agrosciences Llc | Compounds and methods for controlling fungi |
| PL2442809T3 (pl) | 2009-06-17 | 2017-02-28 | Vertex Pharmaceuticals Incorporated | Inhibitory replikacji wirusów grypy |
| US8933227B2 (en) | 2009-08-14 | 2015-01-13 | Boehringer Ingelheim International Gmbh | Selective synthesis of functionalized pyrimidines |
| WO2011018517A1 (en) | 2009-08-14 | 2011-02-17 | Boehringer Ingelheim International Gmbh | Regioselective preparation of 2-amino-5-trifluoromethylpyrimidine derivatives |
| KR20130128435A (ko) * | 2010-12-16 | 2013-11-26 | 버텍스 파마슈티칼스 인코포레이티드 | 인플루엔자 바이러스 복제의 억제제 |
| AU2011343642A1 (en) | 2010-12-16 | 2013-05-02 | Vertex Pharmaceuticals Incorporated | Inhibitors of influenza viruses replication |
| WO2012131399A1 (en) | 2011-04-01 | 2012-10-04 | Astrazeneca Ab | Therapeutic treatment |
| UA118010C2 (uk) | 2011-08-01 | 2018-11-12 | Вертекс Фармасьютікалз Інкорпорейтед | Інгібітори реплікації вірусів грипу |
| SMT201900708T1 (it) | 2011-11-30 | 2020-01-14 | Astrazeneca Ab | Trattamento di combinazione di un cancro |
| AU2013204533B2 (en) | 2012-04-17 | 2017-02-02 | Astrazeneca Ab | Crystalline forms |
| WO2014004543A1 (en) * | 2012-06-25 | 2014-01-03 | Mone Zaidi Consulting, Inc. | Combination cancer therapy using bisphosphonates and anti-egfr agents |
| PL2935248T3 (pl) | 2012-12-21 | 2018-07-31 | Plexxikon Inc | Związki i sposoby modulacji kinaz i wskazania dla nich |
| GB2515785A (en) * | 2013-07-03 | 2015-01-07 | Redx Pharma Ltd | Compounds |
| CN104540820B (zh) * | 2013-07-16 | 2016-12-21 | 杭州普晒医药科技有限公司 | 阿法替尼酸加成盐及其晶型、其制备方法及药物组合物 |
| EP3421468B1 (en) * | 2013-11-13 | 2020-11-04 | Vertex Pharmaceuticals Incorporated | Methods of preparing inhibitors of influenza viruses replication |
| LT3068776T (lt) | 2013-11-13 | 2019-08-12 | Vertex Pharmaceuticals Incorporated | Gripo virusų replikacijos inhibitoriai |
| SG11201608303QA (en) | 2014-04-04 | 2016-11-29 | Del Mar Pharmaceuticals | Use of dianhydrogalactitol and analogs or derivatives thereof to treat non-small-cell carcinoma of the lung and ovarian cancer |
| WO2016183120A1 (en) | 2015-05-13 | 2016-11-17 | Vertex Pharmaceuticals Incorporated | Inhibitors of influenza viruses replication |
| JP6704416B2 (ja) | 2015-05-13 | 2020-06-03 | 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Ｖｅｒｔｅｘ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃｏｒｐｏｒａｔｅｄ | インフルエンザウイルスの複製の阻害剤を調製する方法 |
| WO2016210345A1 (en) * | 2015-06-25 | 2016-12-29 | The California Institute For Biomedical Research | Composition and methods for inhibiting mammalian sterile 20-like kinase 1 |
| JP2018537526A (ja) * | 2015-11-02 | 2018-12-20 | ユニバーシティ オブ ロチェスター | ボルテゾミブ複合体及びその使用方法 |
| EP3383875B1 (en) | 2015-11-30 | 2022-02-09 | Council Of Scientific & Industrial Research | 3-pyrimidinyl pyrrolo [2,3-b] pyridine as anticancer agents and the process for the preparation thereof |
| JOP20210298A1 (ar) | 2019-05-14 | 2023-01-30 | Provention Bio Inc | طرق وتركيبات للوقاية من مرض السكري من النوع الأول |
| CN110372713B (zh) * | 2019-08-15 | 2022-05-17 | 广州市汉普医药有限公司 | 一种普拉洛芬的精制纯化方法 |
| MX2022007265A (es) * | 2019-12-20 | 2022-09-09 | Nuevolution As | Compuestos activos frente a receptores nucleares. |
| US11739088B2 (en) | 2020-04-29 | 2023-08-29 | Plexxikon Inc. | Synthesis of heterocyclic compounds |
| KR20230092863A (ko) | 2020-06-11 | 2023-06-26 | 프로벤션 바이오, 인코포레이티드 | 제1형 당뇨병을 예방하기 위한 방법 및 조성물 |
| WO2023107705A1 (en) | 2021-12-10 | 2023-06-15 | Incyte Corporation | Bicyclic amines as cdk12 inhibitors |
Family Cites Families (78)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL83821A0 (en) | 1986-09-10 | 1988-02-29 | Sandoz Ag | Azaindole and indolizine derivatives,their production and pharmaceutical compositions containing them |
| JP2779403B2 (ja) | 1988-11-29 | 1998-07-23 | 日本バイエルアグロケム株式会社 | 殺虫性ニトロ化合物 |
| US5304121A (en) | 1990-12-28 | 1994-04-19 | Boston Scientific Corporation | Drug delivery system making use of a hydrogel polymer coating |
| FR2687402B1 (fr) | 1992-02-14 | 1995-06-30 | Lipha | Nouveaux azaindoles, procedes de preparation et medicaments les contenant. |
| US5994341A (en) | 1993-07-19 | 1999-11-30 | Angiogenesis Technologies, Inc. | Anti-angiogenic Compositions and methods for the treatment of arthritis |
| WO1995033748A1 (en) | 1994-06-09 | 1995-12-14 | Smithkline Beecham Corporation | Endothelin receptor antagonists |
| US6221894B1 (en) | 1995-03-20 | 2001-04-24 | Merck & Co., Inc. | Nodulisporic acid derivatives |
| US6099562A (en) | 1996-06-13 | 2000-08-08 | Schneider (Usa) Inc. | Drug coating with topcoat |
| GB9721437D0 (en) | 1997-10-10 | 1997-12-10 | Glaxo Group Ltd | Heteroaromatic compounds and their use in medicine |
| DE69928414T2 (de) * | 1998-09-18 | 2006-08-03 | Abbott Gmbh & Co. Kg | 4-aminopyrrolopyrimidine als kinaseinhibitoren |
| WO2000040581A1 (en) | 1999-01-07 | 2000-07-13 | American Home Products Corporation | 3,4-dihydro-2h-benzo[1,4]oxazine derivatives |
| US6265403B1 (en) | 1999-01-20 | 2001-07-24 | Merck & Co., Inc. | Angiogenesis inhibitors |
| US20030153560A1 (en) * | 1999-04-23 | 2003-08-14 | Salituro Francesco G. | Inhibitors of c-Jun N-terminal kinases (JNK) |
| CA2373883A1 (en) | 1999-07-02 | 2001-01-11 | Stuart A. Lipton | Method of reducing neuronal injury or apoptosis |
| US7041277B2 (en) | 2000-03-10 | 2006-05-09 | Cadbury Adams Usa Llc | Chewing gum and confectionery compositions with encapsulated stain removing agent compositions, and methods of making and using the same |
| CA2421502A1 (en) | 2000-09-06 | 2002-03-14 | Ortho-Mcneil Pharmaceutical, Inc. | A method for treating allergies |
| PL363241A1 (en) | 2000-12-22 | 2004-11-15 | Wyeth | Heterocyclindazole and azaindazole compounds as 5-hydroxytryptamine-6 ligands |
| CA2439263C (en) | 2001-03-02 | 2012-10-23 | Frank Becker | Three hybrid assay system |
| DK1392697T3 (da) | 2001-03-14 | 2005-02-14 | Wyeth Corp | Antidepressive azaheterocyclylmethylderivater af 2,3-dihydro-1,4-dioxino[2.3-f]quinolin |
| US7081454B2 (en) * | 2001-03-28 | 2006-07-25 | Bristol-Myers Squibb Co. | Tyrosine kinase inhibitors |
| EP1381600A1 (en) | 2001-04-24 | 2004-01-21 | Wyeth, A Corporation of the State of Delaware | Antidepressant azaheterocyclylmethyl derivatives of 2,3-dihydro-1,4-benzodioxan |
| US6656950B2 (en) | 2001-04-25 | 2003-12-02 | Wyeth | Antidepressant azaheterocyclylmethyl derivatives of 1,4-dioxino[2,3-b]pyridine |
| DK1401839T5 (da) | 2001-04-26 | 2006-03-13 | Wyeth Corp | Antidepressive (SSSRI) azaheterocyclylmethylderivater af 7,8-dihydro-3H-6,9-dioxa-1,3-diazacyclopenta[a]naphthalen |
| US6617327B2 (en) | 2001-04-26 | 2003-09-09 | Wyeth | Antidepressant azaheterocyclylmethyl derivatives of 2,3-dihydro-1,4-dioxino[2,3-f]quinoxaline |
| US6552049B2 (en) | 2001-04-26 | 2003-04-22 | Wyeth | Antidepressant azaheterocyclylmethyl derivatives of oxaheterocycle-fused-[1,4]-benzodioxans |
| DE60201447T2 (de) | 2001-04-30 | 2006-02-23 | Wyeth | Antidepressive azaheterocyclylmethylderivate von 7,8-dihydro-1,6,9-trioxa-3-azacyclopenta(a)naphthalin |
| EP1387845A2 (en) | 2001-05-17 | 2004-02-11 | Wyeth | PROCESSES FOR THE SYNTHESIS OF DERIVATIVES OF 2,3-DIHYDRO-1,4-DIOXINO-(2,3-f) QUINOLINE |
| ATE432929T1 (de) * | 2001-06-15 | 2009-06-15 | Vertex Pharma | 5-(2-aminopyrimidin-4-yl)benzisoxazole als proteinkinasehemmer |
| GB0115109D0 (en) | 2001-06-21 | 2001-08-15 | Aventis Pharma Ltd | Chemical compounds |
| US20040236110A1 (en) * | 2001-09-26 | 2004-11-25 | Ladouceur Gaetan H | Substituted 3-pyridyl indoles and indazoles as c17,20 lyase inhibitors |
| TW200306819A (en) * | 2002-01-25 | 2003-12-01 | Vertex Pharma | Indazole compounds useful as protein kinase inhibitors |
| AU2003237121A1 (en) | 2002-04-26 | 2003-11-10 | Vertex Pharmaceuticals Incorporated | Pyrrole derivatives as inhibitors of erk2 and uses thereof |
| JP2005529895A (ja) * | 2002-04-26 | 2005-10-06 | ファイザー・プロダクツ・インク | Ｎ置換へテロアリールオキシ−アリール−スピロ−ピリミジン−２，４，６−トリオンメタロプロテイナーゼ阻害剤 |
| UA78999C2 (en) | 2002-06-04 | 2007-05-10 | Wyeth Corp | 1-(aminoalkyl)-3-sulfonylazaindoles as ligands of 5-hydroxytryptamine-6 |
| KR20050032105A (ko) * | 2002-08-02 | 2005-04-06 | 버텍스 파마슈티칼스 인코포레이티드 | Ｇｓｋ-3의 억제제로서 유용한 피라졸 조성물 |
| SE0202463D0 (sv) | 2002-08-14 | 2002-08-14 | Astrazeneca Ab | Novel compounds |
| WO2004037814A1 (en) * | 2002-10-25 | 2004-05-06 | Vertex Pharmaceuticals Incorporated | Indazolinone compositions useful as kinase inhibitors |
| JPWO2004043936A1 (ja) * | 2002-11-14 | 2006-03-09 | 協和醗酵工業株式会社 | Ｐｌｋ阻害剤 |
| RS52386B (sr) | 2003-02-26 | 2013-02-28 | Boehringer Ingelheim Pharma Gmbh & Co.Kg. | Dihidropteridinoni, postupak za njihovo pripremanje i njihova primena kao leka |
| EP2295433A3 (en) | 2003-03-06 | 2011-07-06 | Eisai R&D Management Co., Ltd. | JNK inhibitors |
| US7375228B2 (en) | 2003-03-17 | 2008-05-20 | Takeda San Diego, Inc. | Histone deacetylase inhibitors |
| GB0308466D0 (en) | 2003-04-11 | 2003-05-21 | Novartis Ag | Organic compounds |
| WO2005000813A1 (en) | 2003-05-30 | 2005-01-06 | Imclone Systems Incorporated | Heteroarylamino-phenylketone derivatives and their use as kinase inhibitors |
| WO2004106298A1 (en) | 2003-05-30 | 2004-12-09 | Janssen Pharmaceutica N.V. | Indole derivatives with an improved antipsychotic activity |
| AR045595A1 (es) | 2003-09-04 | 2005-11-02 | Vertex Pharma | Composiciones utiles como inhibidores de proteinas quinasas |
| WO2005044181A2 (en) | 2003-09-09 | 2005-05-19 | Temple University-Of The Commonwealth System Of Higher Education | Protection of tissues and cells from cytotoxic effects of ionizing radiation by abl inhibitors |
| CN1897950A (zh) * | 2003-10-14 | 2007-01-17 | 惠氏公司 | 稠合芳基和杂芳基衍生物及其使用方法 |
| 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 |
| PL2332940T3 (pl) * | 2004-03-30 | 2013-03-29 | Vertex Pharma | Azaindole użyteczne jako inhibitory JAK i innych kinaz białkowych |
| RU2006138621A (ru) | 2004-04-02 | 2008-05-10 | Вертекс Фармасьютикалз Инкорпорейтед (Us) | Азаиндолы, полезные в качестве ингибиторов rock и других протеинкиназ |
| ITMI20040874A1 (it) | 2004-04-30 | 2004-07-30 | Ist Naz Stud Cura Dei Tumori | Derivati indolici ed azaindolici con azione antitumorale |
| WO2006009755A2 (en) | 2004-06-17 | 2006-01-26 | Plexxikon, Inc. | Azaindoles modulating c-kit activity and uses therefor |
| US20060122213A1 (en) | 2004-06-30 | 2006-06-08 | Francoise Pierard | Azaindoles useful as inhibitors of protein kinases |
| WO2006015123A1 (en) * | 2004-07-27 | 2006-02-09 | Sgx Pharmaceuticals, Inc. | Pyrrolo-pyridine kinase modulators |
| US7718801B2 (en) * | 2004-08-31 | 2010-05-18 | Banyu Pharmaceutical Co., Ltd. | Substituted imidazole derivative |
| GB0420719D0 (en) | 2004-09-17 | 2004-10-20 | Addex Pharmaceuticals Sa | Novel allosteric modulators |
| WO2006038001A1 (en) | 2004-10-06 | 2006-04-13 | Celltech R & D Limited | Aminopyrimidine derivatives as jnk inhibitors |
| WO2006050076A1 (en) * | 2004-10-29 | 2006-05-11 | Janssen Pharmaceutica, N.V. | Pyrimidinyl substituted fused-pyrrolyl compounds useful in treating kinase disorders |
| CA2587926A1 (en) * | 2004-11-22 | 2006-06-01 | Vertex Pharmaceuticals Incorporated | Bicyclic inhibitors or rho kinase |
| KR20070095952A (ko) * | 2004-12-16 | 2007-10-01 | 버텍스 파마슈티칼스 인코포레이티드 | 염증성 질환, 증식성 질환 및 면역학적으로 매개된 질환치료용 Ｔｅｃ 계열 단백질 키나제의 억제제로서 유용한피리드-2-온 |
| CA2596830A1 (en) | 2005-02-03 | 2006-09-14 | Vertex Pharmaceuticals Incorporated | Pyrrolopyrimidines useful as inhibitors of protein kinase |
| CN101218241B (zh) * | 2005-05-16 | 2011-02-16 | Irm责任有限公司 | 用作蛋白激酶抑制剂的吡咯并吡啶衍生物 |
| WO2006127587A1 (en) * | 2005-05-20 | 2006-11-30 | Vertex Pharmaceuticals Incorporated | Pyrrolopyridines useful as inhibitors of protein kinase |
| CN102603581B (zh) | 2005-06-22 | 2015-06-24 | 普莱希科公司 | 作为蛋白质激酶抑制剂的吡咯并[2,3-b]吡啶衍生物 |
| TW200800921A (en) | 2005-09-19 | 2008-01-01 | Astrazeneca Ab | Novel compounds |
| KR20080063809A (ko) | 2005-09-30 | 2008-07-07 | 버텍스 파마슈티칼스 인코포레이티드 | 야누스 키나아제의 억제제로서 유용한 데아자퓨린 |
| TWI424999B (zh) | 2006-01-17 | 2014-02-01 | Vertex Pharma | 適合作為傑納斯激酶（ｊａｎｕｓ ｋｉｎａｓｅ）抑制劑之氮雜吲哚 |
| WO2007095223A2 (en) * | 2006-02-14 | 2007-08-23 | Vertex Pharmaceuticals Incorporated | Pyrrolo(3,2-c) pyridines useful as inhibitors of protein kinases |
| DE102006012617A1 (de) | 2006-03-20 | 2007-09-27 | Merck Patent Gmbh | 4-(Pyrrolopyridinyl)-pyrimidinyl-2-amin-derivate |
| CA2648250A1 (en) * | 2006-04-05 | 2007-10-18 | Vertex Pharmaceuticals Incorporated | Deazapurines useful as inhibitors of janus kinases |
| CN101541783B (zh) * | 2006-06-30 | 2014-10-01 | 苏尼西斯制药有限公司 | 吡啶酮基pdk1抑制剂 |
| WO2008079346A1 (en) * | 2006-12-21 | 2008-07-03 | Vertex Pharmaceuticals Incorporated | 5-cyan0-4- (pyrrolo [2, 3b] pyridine-3-yl) -pyrimidine derivatives useful as protein kinase inhibitors |
| WO2008112646A1 (en) | 2007-03-09 | 2008-09-18 | Vertex Pharmaceuticals Incorporated | Aminopyridines useful as inhibitors of protein kinases |
| AU2008226466B2 (en) | 2007-03-09 | 2013-06-13 | Vertex Pharmaceuticals Incorporated | Aminopyrimidines useful as inhibitors of protein kinases |
| NZ579446A (en) | 2007-03-09 | 2012-02-24 | Vertex Pharma | Aminopyrimidines useful as inhibitors of protein kinases |
| WO2009073300A1 (en) * | 2007-11-02 | 2009-06-11 | Vertex Pharmaceuticals Incorporated | [1h- pyrazolo [3, 4-b] pyridine-4-yl] -phenyle or -pyridin-2-yle derivatives as protein kinase c-theta |
| EP2262498A2 (en) | 2008-03-10 | 2010-12-22 | Vertex Pharmceuticals Incorporated | Pyrimidines and pyridines useful as inhibitors of protein kinases |
-
2007
- 2007-12-21 WO PCT/US2007/026190 patent/WO2008079346A1/en not_active Ceased
- 2007-12-21 AR ARP070105844A patent/AR064675A1/es not_active Application Discontinuation
- 2007-12-21 KR KR1020097015174A patent/KR20090091350A/ko not_active Withdrawn
- 2007-12-21 CN CN200780051641A patent/CN101678022A/zh active Pending
- 2007-12-21 AU AU2007338754A patent/AU2007338754A1/en not_active Abandoned
- 2007-12-21 MX MX2009006700A patent/MX2009006700A/es not_active Application Discontinuation
- 2007-12-21 NZ NZ577798A patent/NZ577798A/en not_active IP Right Cessation
- 2007-12-21 CA CA002673472A patent/CA2673472A1/en not_active Abandoned
- 2007-12-21 EP EP14167221.2A patent/EP2815750A1/en not_active Withdrawn
- 2007-12-21 JP JP2009542940A patent/JP5406039B2/ja not_active Expired - Fee Related
- 2007-12-21 EP EP07867948.7A patent/EP2124951B1/en not_active Not-in-force
- 2007-12-21 TW TW096149620A patent/TW200838517A/zh unknown
- 2007-12-21 US US12/448,489 patent/US8247421B2/en not_active Expired - Fee Related
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2013
- 2013-08-07 US US13/961,218 patent/US8962642B2/en not_active Expired - Fee Related
- 2013-10-31 JP JP2013227246A patent/JP2014051516A/ja active Pending
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| AR064675A1 (es) | 2009-04-15 |
| CN101678022A (zh) | 2010-03-24 |
| US8962642B2 (en) | 2015-02-24 |
| NO20092668L (no) | 2009-09-21 |
| JP5406039B2 (ja) | 2014-02-05 |
| EP2124951B1 (en) | 2014-05-21 |
| EP2815750A1 (en) | 2014-12-24 |
| US20120309963A1 (en) | 2012-12-06 |
| WO2008079346A1 (en) | 2008-07-03 |
| JP2014051516A (ja) | 2014-03-20 |
| EP2124951A1 (en) | 2009-12-02 |
| MX2009006700A (es) | 2009-06-30 |
| US20100189773A1 (en) | 2010-07-29 |
| CA2673472A1 (en) | 2008-07-03 |
| TW200838517A (en) | 2008-10-01 |
| KR20090091350A (ko) | 2009-08-27 |
| US20140045812A1 (en) | 2014-02-13 |
| US8530489B2 (en) | 2013-09-10 |
| NZ577798A (en) | 2012-04-27 |
| JP2010514676A (ja) | 2010-05-06 |
| US8247421B2 (en) | 2012-08-21 |
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