RU2435769C2 - Пирролопиридины, полезные в качестве ингибиторов протеинкиназы - Google Patents
Пирролопиридины, полезные в качестве ингибиторов протеинкиназы Download PDFInfo
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- RU2435769C2 RU2435769C2 RU2007147455/04A RU2007147455A RU2435769C2 RU 2435769 C2 RU2435769 C2 RU 2435769C2 RU 2007147455/04 A RU2007147455/04 A RU 2007147455/04A RU 2007147455 A RU2007147455 A RU 2007147455A RU 2435769 C2 RU2435769 C2 RU 2435769C2
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Landscapes
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US68355405P | 2005-05-20 | 2005-05-20 | |
| US60/683,554 | 2005-05-20 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2011133825/04A Division RU2011133825A (ru) | 2005-05-20 | 2011-08-11 | Пирролопиридины, полезные в качестве ингибиторов протеинкиназы |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2007147455A RU2007147455A (ru) | 2009-06-27 |
| RU2435769C2 true RU2435769C2 (ru) | 2011-12-10 |
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Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2007147455/04A RU2435769C2 (ru) | 2005-05-20 | 2006-05-22 | Пирролопиридины, полезные в качестве ингибиторов протеинкиназы |
| RU2011133825/04A RU2011133825A (ru) | 2005-05-20 | 2011-08-11 | Пирролопиридины, полезные в качестве ингибиторов протеинкиназы |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2011133825/04A RU2011133825A (ru) | 2005-05-20 | 2011-08-11 | Пирролопиридины, полезные в качестве ингибиторов протеинкиназы |
Country Status (16)
| Country | Link |
|---|---|
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2634723C2 (ru) * | 2013-04-02 | 2017-11-03 | Ф. Хоффманн-Ля Рош Аг | Ингибиторы тирозинкиназы брутона |
| RU2649575C1 (ru) * | 2014-02-04 | 2018-04-04 | Тайхо Фармасьютикал Ко., Лтд. | Азаиндольное производное |
Families Citing this family (172)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI1696920T1 (sl) | 2003-12-19 | 2015-02-27 | Plexxikon Inc. | Spojine in postopki za razvoj modulatorjev ret |
| BRPI0509369B1 (pt) | 2004-03-30 | 2021-08-03 | Vertex Pharmaceuticals Incorporated | Compostos azaindóis úteis como inibidores de jak e outras proteína cinases e composição farmacêutica |
| US7498342B2 (en) | 2004-06-17 | 2009-03-03 | Plexxikon, Inc. | Compounds modulating c-kit activity |
| JP2008545652A (ja) | 2005-05-17 | 2008-12-18 | プレキシコン，インコーポレーテッド | ｃ−ｋｉｔおよびｃ−ｆｍｓ活性を調節する化合物およびその用途 |
| ZA200710379B (en) * | 2005-05-20 | 2009-05-27 | Vertex Pharma | Pyrrolopyridines useful as inhibitors of protein kinase |
| WO2007002325A1 (en) | 2005-06-22 | 2007-01-04 | Plexxikon, Inc. | Pyrrolo[2,3-b] pyridine derivatives as protein kinase inhibitors |
| EP2251341A1 (en) * | 2005-07-14 | 2010-11-17 | Astellas Pharma Inc. | Heterocyclic Janus kinase 3 inhibitors |
| US8163767B2 (en) | 2005-07-14 | 2012-04-24 | Astellas Pharma Inc. | Heterocyclic Janus Kinase 3 inhibitors |
| WO2007038215A1 (en) | 2005-09-22 | 2007-04-05 | Incyte Corporation | Tetracyclic inhibitors of janus kinases |
| AU2015201850B2 (en) * | 2005-12-13 | 2017-03-02 | Incyte Holdings Corporation | Heteroaryl substituted pyrrolo[2,3-b]pyridines and pyrrolo[2,3-b]pyrimidines as Janus kinase inhibitors |
| EP2474545B1 (en) * | 2005-12-13 | 2016-11-09 | Incyte Holdings Corporation | Heteroaryl substituted pyrrolo[2,3-b]pyridines and pyrrolo[2,3-b]pyrimidines as Janus kinase inhibitors |
| EP1968568A4 (en) * | 2005-12-22 | 2011-04-13 | Glaxosmithkline Llc | HEMMER OF NUTS ACTIVITY |
| CN102532133A (zh) | 2006-01-17 | 2012-07-04 | 沃泰克斯药物股份有限公司 | 适用作詹纳斯激酶抑制剂的吖吲哚类 |
| WO2007082808A2 (en) * | 2006-01-18 | 2007-07-26 | F. Hoffmann-La Roche Ag | Thiazoles as 11 beta-hsd1 inhibitors |
| WO2007084667A2 (en) * | 2006-01-19 | 2007-07-26 | Osi Pharmaceutical, Inc. | Fused heterobicyclic kinase inhibitors |
| RU2008143361A (ru) * | 2006-04-05 | 2010-05-10 | Вертекс Фармасьютикалз Инкорпорейтед (Us) | Деазапурины в качестве ингибиторов янус-киназ |
| EP2865381A1 (en) * | 2006-05-18 | 2015-04-29 | Pharmacyclics, Inc. | ITK inhibitors for treating blood cell malignancies |
| WO2008006039A1 (en) | 2006-07-06 | 2008-01-10 | Array Biopharma Inc. | Dihydrothieno pyrimidines as akt protein kinase inhibitors |
| US8063050B2 (en) | 2006-07-06 | 2011-11-22 | Array Biopharma Inc. | Hydroxylated and methoxylated pyrimidyl cyclopentanes as AKT protein kinase inhibitors |
| WO2008006025A1 (en) | 2006-07-06 | 2008-01-10 | Array Biopharma Inc. | Dihydrofuro pyrimidines as akt protein kinase inhibitors |
| ES2372955T3 (es) * | 2006-07-06 | 2012-01-30 | Array Biopharma, Inc. | Ciclopenta[d]pirimidinas como inhibidores de la proteína cinasa akt. |
| JP5244118B2 (ja) * | 2006-11-10 | 2013-07-24 | ブリストル−マイヤーズ スクイブ カンパニー | 新規キナーゼ阻害剤 |
| WO2008063888A2 (en) | 2006-11-22 | 2008-05-29 | Plexxikon, Inc. | Compounds modulating c-fms and/or c-kit activity and uses therefor |
| US8071779B2 (en) | 2006-12-18 | 2011-12-06 | Inspire Pharmaceuticals, Inc. | Cytoskeletal active rho kinase inhibitor compounds, composition and use |
| AU2007336811A1 (en) | 2006-12-21 | 2008-07-03 | Plexxikon, Inc. | Compounds and methods for kinase modulation, and indications therefor |
| PE20081581A1 (es) | 2006-12-21 | 2008-11-12 | Plexxikon Inc | COMPUESTOS PIRROLO[2,3-b]PIRIDINAS COMO MODULADORES DE QUINASA |
| WO2008079909A1 (en) | 2006-12-21 | 2008-07-03 | Plexxikon, Inc. | Pyrrolo [2,3-b] pyridines as kinase modulators |
| AR064675A1 (es) | 2006-12-21 | 2009-04-15 | Vertex Pharma | Derivados heterociclicos de pirrolo- [2,3-b] piridina, inhibidores de proteinquinasas plk, composiciones farmaceuticas que los contienen, proceso de preparacion y uso de los mismos en trastornos hiperproliferativos |
| WO2008079965A1 (en) | 2006-12-22 | 2008-07-03 | Incyte Corporation | Substituted heterocycles as janus kinase inhibitors |
| TW200900061A (en) | 2007-01-12 | 2009-01-01 | Astellas Pharma Inc | Condensed pyridine compound |
| CA2681516A1 (en) * | 2007-03-22 | 2008-09-25 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of janus kinases |
| JP5603770B2 (ja) | 2007-05-31 | 2014-10-08 | 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 | Ｃｃｒ２受容体拮抗薬およびその使用 |
| GB0710528D0 (en) * | 2007-06-01 | 2007-07-11 | Glaxo Group Ltd | Novel compounds |
| DK2173752T4 (en) | 2007-06-13 | 2022-08-01 | Incyte Holdings Corp | Salte af janus-kinase-inhibitor (r)-3-(4-(7h-pyrrolo(2,3-d)pyrimidin-4-yl)-1h-pyrazol-1-yl)-3-cyclopentylpropannitril |
| CL2008001709A1 (es) | 2007-06-13 | 2008-11-03 | Incyte Corp | Compuestos derivados de pirrolo [2,3-b]pirimidina, moduladores de quinasas jak; composicion farmaceutica; y uso en el tratamiento de enfermedades tales como cancer, psoriasis, artritis reumatoide, entre otras. |
| ES2533557T3 (es) * | 2007-07-05 | 2015-04-13 | Array Biopharma, Inc. | Pirimidil ciclopentanos como inhibidores de proteína cinasa AKT |
| SG185274A1 (en) | 2007-07-05 | 2012-11-29 | Array Biopharma Inc | Pyrimidyl cyclopentanes as akt protein kinase inhibitors |
| US9409886B2 (en) | 2007-07-05 | 2016-08-09 | Array Biopharma Inc. | Pyrimidyl cyclopentanes as AKT protein kinase inhibitors |
| US8846683B2 (en) | 2007-07-05 | 2014-09-30 | Array Biopharma, Inc. | Pyrimidyl cyclopentanes as Akt protein kinase inhibitors |
| BRPI0814423B1 (pt) | 2007-07-17 | 2022-04-19 | Plexxikon, Inc | Compostos que modulam quinase e composição farmacêutica compreendendo os mesmos |
| EP2242755B1 (en) | 2008-01-08 | 2012-09-12 | Array Biopharma, Inc. | Pyrrolopyridines as kinase inhibitors |
| ES2392014T3 (es) * | 2008-01-09 | 2012-12-03 | Array Biopharma, Inc. | Pirazolopiridinas como inhibidores de la cinasa |
| US8835434B2 (en) * | 2008-01-09 | 2014-09-16 | Array Biopharma, Inc. | Hydroxylated pyrimidyl cyclopentanes as akt protein kinase inhibitors |
| KR101624752B1 (ko) * | 2008-01-09 | 2016-05-26 | 어레이 바이오파마 인크. | Ａｋｔ 단백질 키나제 저해물질로써의 수산화된 피리미딜 시클로펜탄 |
| GB0801416D0 (en) * | 2008-01-25 | 2008-03-05 | Piramed Ltd | Pharmaceutical compounds |
| JP2011513483A (ja) * | 2008-03-10 | 2011-04-28 | 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 | タンパク質キナーゼの阻害剤として有用なピリミジンおよびピリジン |
| US8158616B2 (en) | 2008-03-11 | 2012-04-17 | Incyte Corporation | Azetidine and cyclobutane derivatives as JAK inhibitors |
| GB0804592D0 (en) * | 2008-03-12 | 2008-04-16 | Glaxo Group Ltd | Novel compounds |
| CL2009001152A1 (es) | 2008-05-13 | 2009-10-16 | Array Biopharma Inc | Compuestos derivados de n-(4-(cicloalquilo nitrogenado-1-il)-1h-pirrolo[2,3-b]piridin-3-il)amida, inhibidores de cinasa; proceso de preparacion; composicion farmaceutica; y su uso para el tratamiento de una enfermedad proliferativa. |
| US9447049B2 (en) | 2010-03-01 | 2016-09-20 | University Of Tennessee Research Foundation | Compounds for treatment of cancer |
| US9029408B2 (en) | 2008-06-16 | 2015-05-12 | Gtx, Inc. | Compounds for treatment of cancer |
| PL3289876T3 (pl) | 2008-06-16 | 2022-11-21 | University Of Tennessee Research Foundation | Związki do leczenia nowotworu |
| US8822513B2 (en) | 2010-03-01 | 2014-09-02 | Gtx, Inc. | Compounds for treatment of cancer |
| CL2009001884A1 (es) * | 2008-10-02 | 2010-05-14 | Incyte Holdings Corp | Uso de 3-ciclopentil-3-[4-(7h-pirrolo[2,3-d]pirimidin-4-il)-1h-pirazol-1-il)propanonitrilo, inhibidor de janus quinasa, y uso de una composición que lo comprende para el tratamiento del ojo seco. |
| DE102008052943A1 (de) | 2008-10-23 | 2010-04-29 | Merck Patent Gmbh | Azaindolderivate |
| DK2379525T3 (en) | 2008-12-19 | 2015-10-19 | Boehringer Ingelheim Int | Cyclic pyrimidin-4-carboxamides, as CCR2 receptor antagonists for the treatment of inflammation, asthma and COPD |
| JP5511942B2 (ja) | 2009-04-03 | 2014-06-04 | エフ ホフマン−ラ ロッシュ アクチェン ゲゼルシャフト | 組成物及びその使用 |
| CA2762174C (en) * | 2009-05-22 | 2018-02-20 | Incyte Corporation | N-(hetero)aryl-pyrrolidine derivatives of pyrazol-4-yl-pyrrolo[2,3-d]pyrimidines and pyrrol-3-yl-pyrrolo[2,3-d]pyrimidines as janus kinase inhibitors |
| TWI484962B (zh) * | 2009-05-22 | 2015-05-21 | Incyte Corp | 作為ｊａｋ抑制劑之３－〔４－（７ｈ－吡咯并〔２，３－ｄ〕嘧啶－４－基）－１ｈ－吡唑－１－基〕辛烷或庚腈 |
| UY32717A (es) | 2009-06-17 | 2011-01-31 | Vertex Pharma | Inhibidores de la replicación de virus de la gripe |
| TW201105674A (en) | 2009-07-08 | 2011-02-16 | Leo Pharma As | Novel JAK receptor and protein tyrosine kinase inhibitors and pharmaceutical use thereof |
| TWI466885B (zh) * | 2009-07-31 | 2015-01-01 | Japan Tobacco Inc | 含氮螺環化合物及其醫藥用途 |
| US8329724B2 (en) | 2009-08-03 | 2012-12-11 | Hoffmann-La Roche Inc. | Process for the manufacture of pharmaceutically active compounds |
| US8569295B2 (en) * | 2009-08-06 | 2013-10-29 | Merck Patent Gmbh | Bicyclic urea compounds |
| BR112012002336A2 (pt) * | 2009-08-07 | 2016-05-31 | Merck Patent Gmbh | compostos aza-heterocíclicos |
| IN2012DN01325A (enExample) | 2009-08-20 | 2015-06-05 | Karus Therapeutics Ltd | |
| TW201113285A (en) | 2009-09-01 | 2011-04-16 | Incyte Corp | Heterocyclic derivatives of pyrazol-4-yl-pyrrolo[2,3-d]pyrimidines as janus kinase inhibitors |
| CA2773182A1 (en) | 2009-09-10 | 2011-03-17 | F. Hoffmann-La Roche Ag | Inhibitors of jak |
| CA2777114C (en) | 2009-10-09 | 2018-10-23 | Incyte Corporation | Hydroxyl, keto, and glucuronide derivatives of 3-(4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h-pyrazol-1-yl)-3-cyclopentylpropanenitrile |
| CA2780190C (en) | 2009-11-06 | 2020-05-05 | Plexxikon, Inc. | Compounds and methods for kinase modulation, and indications therefor |
| NZ599770A (en) | 2009-12-17 | 2014-06-27 | Boehringer Ingelheim Int | New ccr2 receptor antagonists and uses thereof |
| USRE49251E1 (en) | 2010-01-04 | 2022-10-18 | Mapi Pharma Ltd. | Depot systems comprising glatiramer or pharmacologically acceptable salt thereof |
| KR101836538B1 (ko) * | 2010-02-18 | 2018-03-08 | 인사이트 홀딩스 코포레이션 | 야누스 키나아제 억제제로서의 사이클로부탄 및 메틸사이클로부탄 유도체 |
| EP3064204A1 (en) | 2010-03-01 | 2016-09-07 | GTx, Inc. | Compounds for treatment of cancer |
| ME02386B (me) * | 2010-03-10 | 2016-09-20 | Incyte Holdings Corp | Derivati piperidin-4-il azetidina kao inhibitori jak1 |
| US8946218B2 (en) | 2010-05-12 | 2015-02-03 | Boehringer Ingelheim International Gmbh | CCR2 receptor antagonists, method for producing the same, and use thereof as medicaments |
| EP2569298B1 (en) | 2010-05-12 | 2015-11-25 | Boehringer Ingelheim International GmbH | Novel ccr2 receptor antagonists, method for producing the same, and use thereof as medicaments |
| WO2011144501A1 (en) | 2010-05-17 | 2011-11-24 | Boehringer Ingelheim International Gmbh | Ccr2 antagonists and uses thereof |
| SG185567A1 (en) | 2010-05-21 | 2012-12-28 | Incyte Corp | Topical formulation for a jak inhibitor |
| US9018212B2 (en) | 2010-05-25 | 2015-04-28 | Boehringer Ingelheim International Gmbh | Pyridazine carboxamides as CCR2 receptor antagonists |
| WO2011151251A1 (en) | 2010-06-01 | 2011-12-08 | Boehringer Ingelheim International Gmbh | New ccr2 antagonists |
| EP2397482A1 (en) * | 2010-06-15 | 2011-12-21 | Almirall, S.A. | Heteroaryl imidazolone derivatives as jak inhibitors |
| US8933085B2 (en) | 2010-11-19 | 2015-01-13 | Incyte Corporation | Cyclobutyl substituted pyrrolopyridine and pyrrolopyrimidine derivatives as JAK inhibitors |
| US9034884B2 (en) | 2010-11-19 | 2015-05-19 | Incyte Corporation | Heterocyclic-substituted pyrrolopyridines and pyrrolopyrimidines as JAK inhibitors |
| CA2822057A1 (en) | 2010-12-16 | 2012-06-21 | Vertex Pharmaceuticals Incorporated | Inhibitors of influenza viruses replication |
| BR112013017184A2 (pt) * | 2011-01-07 | 2016-09-20 | Leo Pharma As | composto, composição farmacêutica, uso de um composto, e, método para evitar, tratar ou melhorar doenças |
| SI2672967T1 (sl) | 2011-02-07 | 2018-12-31 | Plexxikon Inc. | Spojine in postopki za kinazno modulacijo in indikacije zanjo |
| PT2675451E (pt) | 2011-02-18 | 2015-10-16 | Incyte Corp | Terapia de combinação com inibidores mtor/jak |
| TWI558702B (zh) | 2011-02-21 | 2016-11-21 | 普雷辛肯公司 | 醫藥活性物質的固態形式 |
| ME02998B (me) | 2011-04-01 | 2018-10-20 | Genentech Inc | Kombinacija акт inhibiтor jedinjenja i abiraterona za upotrebu pri terapeutsкim treтiranjima |
| EP2694073B1 (en) | 2011-04-01 | 2018-08-08 | Genentech, Inc. | Combinations of akt and mek inhibitors for treating cancer |
| BR112013032720A2 (pt) | 2011-06-20 | 2016-09-13 | Incyte Corp | "derivados de azetidinil fenil, piridil ou pirazinil carboxamida como inibidores de jak, composição e uso dos referidos derivados" |
| MX2013015147A (es) | 2011-07-05 | 2014-03-27 | Vertex Pharma | Procesos y compuestos intermediarios para producir azaindoles. |
| JP5786258B2 (ja) | 2011-07-15 | 2015-09-30 | 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 | 新規かつ選択的なｃｃｒ２拮抗薬 |
| UA118010C2 (uk) | 2011-08-01 | 2018-11-12 | Вертекс Фармасьютікалз Інкорпорейтед | Інгібітори реплікації вірусів грипу |
| US9358229B2 (en) | 2011-08-10 | 2016-06-07 | Novartis Pharma Ag | JAK PI3K/mTOR combination therapy |
| TW201313721A (zh) | 2011-08-18 | 2013-04-01 | Incyte Corp | 作為ｊａｋ抑制劑之環己基氮雜環丁烷衍生物 |
| UA111854C2 (uk) | 2011-09-07 | 2016-06-24 | Інсайт Холдінгс Корпорейшн | Способи і проміжні сполуки для отримання інгібіторів jak |
| GB201204125D0 (en) | 2012-03-08 | 2012-04-25 | Karus Therapeutics Ltd | Compounds |
| EP2831080B1 (en) | 2012-03-29 | 2017-03-15 | Francis Xavier Tavares | Lactam kinase inhibitors |
| AR091079A1 (es) | 2012-05-18 | 2014-12-30 | Incyte Corp | Derivados de pirrolopirimidina y pirrolopiridina sustituida con piperidinilciclobutilo como inhibidores de jak |
| US9150570B2 (en) | 2012-05-31 | 2015-10-06 | Plexxikon Inc. | Synthesis of heterocyclic compounds |
| WO2014013014A1 (en) | 2012-07-18 | 2014-01-23 | Fundació Privada Centre De Regulació Genòmica (Crg) | Jak inhibitors for activation of epidermal stem cell populations |
| IN2015DN03235A (enExample) | 2012-11-07 | 2015-10-02 | Karus Therapeutics Ltd | |
| TW202228704A (zh) | 2012-11-15 | 2022-08-01 | 美商英塞特控股公司 | 盧梭利替尼之緩釋性劑型 |
| FR3001219A1 (fr) * | 2013-01-22 | 2014-07-25 | Centre Nat Rech Scient | Inhibiteurs de kinases |
| WO2014138212A1 (en) * | 2013-03-06 | 2014-09-12 | Allosteros Therapeutics, Inc. | CaMKII INHIBITORS AND USES THEREOF |
| PT3489239T (pt) | 2013-03-06 | 2021-12-17 | Incyte Holdings Corp | Processos e intermediários para a preparação de um inibidor de jak |
| EP4596051A3 (en) | 2013-03-15 | 2025-10-29 | Pharmacosmos Holding A/s | Hspc-sparing treatments for rb-positive abnormal cellular proliferation |
| CA3152117A1 (en) | 2013-03-15 | 2014-09-18 | G1 Therapeutics, Inc. | Highly active anti-neoplastic and anti-proliferative agents |
| KR101790090B1 (ko) * | 2013-05-02 | 2017-10-25 | 후지필름 가부시키가이샤 | 에칭 방법, 이에 이용하는 에칭액 및 에칭액의 키트, 및 반도체 기판 제품의 제조 방법 |
| KR20160007577A (ko) | 2013-05-10 | 2016-01-20 | 카루스 떼라퓨틱스 리미티드 | 신규한 히스톤 디아세틸라제 억제제들 |
| MY203694A (en) | 2013-08-07 | 2024-07-14 | Incyte Holdings Corp | Sustained release dosage forms for a jak1 inhibitor |
| SI3068776T1 (sl) | 2013-11-13 | 2019-09-30 | Vertex Pharmaceuticals Incorporated | Inhibitorji replikacije virusov influence |
| RU2019104421A (ru) | 2013-11-13 | 2019-04-17 | Вертекс Фармасьютикалз Инкорпорейтед | Способы получения ингибиторов репликации вирусов гриппа |
| GB201402431D0 (en) | 2014-02-12 | 2014-03-26 | Karus Therapeutics Ltd | Compounds |
| EP2924026A1 (en) | 2014-03-28 | 2015-09-30 | Novartis Tiergesundheit AG | Aminosulfonylmethylcyclohexanes as JAK inhibitors |
| WO2015161288A1 (en) | 2014-04-17 | 2015-10-22 | G1 Therapeutics, Inc. | Tricyclic lactams for use as anti-neoplastic and anti-proliferative agents |
| BR112016026641B1 (pt) * | 2014-05-28 | 2023-03-14 | Astrazeneca Ab | Processos para a preparação de azd5363 e novo intemediário utilizado nos mesmos |
| US9498467B2 (en) | 2014-05-30 | 2016-11-22 | Incyte Corporation | Treatment of chronic neutrophilic leukemia (CNL) and atypical chronic myeloid leukemia (aCML) by inhibitors of JAK1 |
| CN107108581B (zh) * | 2014-08-21 | 2020-06-23 | 百时美施贵宝公司 | 作为强效rock抑制剂的回接苯甲酰胺衍生物 |
| AU2015311730A1 (en) | 2014-09-05 | 2017-04-20 | Allosteros Therapeutics, Inc | Camkii inhibitors and uses thereof |
| EP3191098A4 (en) | 2014-09-12 | 2018-04-25 | G1 Therapeutics, Inc. | Combinations and dosing regimes to treat rb-positive tumors |
| WO2016040848A1 (en) | 2014-09-12 | 2016-03-17 | G1 Therapeutics, Inc. | Treatment of rb-negative tumors using topoisomerase inhibitors in combination with cyclin dependent kinase 4/6 inhibitors |
| GB201419228D0 (en) | 2014-10-29 | 2014-12-10 | Karus Therapeutics Ltd | Compounds |
| GB201419264D0 (en) | 2014-10-29 | 2014-12-10 | Karus Therapeutics Ltd | Compounds |
| CN105837572B (zh) * | 2015-02-02 | 2019-04-19 | 四川大学 | N-取代苯基酰胺衍生物及其制备方法和用途 |
| EP3294735B8 (en) | 2015-05-13 | 2022-01-05 | Vertex Pharmaceuticals Incorporated | Inhibitors of influenza viruses replication |
| EP3294717B1 (en) | 2015-05-13 | 2020-07-29 | Vertex Pharmaceuticals Inc. | Methods of preparing inhibitors of influenza viruses replication |
| BR112017028492B1 (pt) | 2015-07-02 | 2023-12-26 | Centrexion Therapeutics Corporation | Citrato de (4-((3r,4r)-3-metoxitetra-hidro-piran-4- ilamino)piperidin-1-il) (5- metil-6-(((2r, 6s)-6-(p-tolil) tetra-hidro-2h-piran-2-il)metilamino)pirimidin-4-il) metanona, seu uso e seu método de preparação, e composição farmacêutica |
| GB201514760D0 (en) | 2015-08-19 | 2015-09-30 | Karus Therapeutics Ltd | Compounds and method of use |
| GB201514751D0 (en) | 2015-08-19 | 2015-09-30 | Karus Therapeutics Ltd | Compounds |
| GB201514754D0 (en) | 2015-08-19 | 2015-09-30 | Karus Therapeutics Ltd | Compounds |
| GB201514758D0 (en) | 2015-08-19 | 2015-09-30 | Karus Therapeutics Ltd | Formulation |
| EP3360878B9 (en) | 2015-12-11 | 2021-05-05 | Sichuan Kelun-Biotech Biopharmaceutical Co., Ltd. | Azetidine derivative, preparation method therefor, and use thereof |
| CN106928252B (zh) * | 2015-12-31 | 2019-09-27 | 成都先导药物开发股份有限公司 | 一种抑制rock的化合物及其制备方法与应用 |
| CN109790158B (zh) * | 2016-07-26 | 2022-06-24 | 苏州隆博泰药业有限公司 | 作为jak抑制剂杂环化合物，该化合物的盐类及其治疗用途 |
| US12097292B2 (en) | 2016-08-28 | 2024-09-24 | Mapi Pharma Ltd. | Process for preparing microparticles containing glatiramer acetate |
| LT3506921T (lt) | 2016-08-31 | 2023-08-10 | Mapi Pharma Ltd | Ilgesnio atpalaidavimo sistemos, kuriose yra glatiramero acetato |
| WO2018041989A1 (en) | 2016-09-02 | 2018-03-08 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for diagnosing and treating refractory celiac disease type 2 |
| AU2018239798B2 (en) * | 2017-03-23 | 2020-08-27 | Daegu Gyeongbuk Institute Of Science And Technology | Pyrrolo-pyridine derivative compound, method for preparing same, and pharmaceutical composition containing same as active ingredient for prevention or treatment of protein kinase-related diseases |
| BR112019017724A2 (pt) | 2017-03-26 | 2020-03-31 | Mapi Pharma Ltd. | Sistemas depot de glatiramer para tratar formas progressivas de esclerose múltipla |
| CN110582491B (zh) * | 2017-06-30 | 2023-09-29 | 北京泰德制药股份有限公司 | Rho相关蛋白激酶抑制剂、包含其的药物组合物及其制备方法和用途 |
| EP3421465B1 (en) | 2017-06-30 | 2022-10-26 | Beijing Tide Pharmaceutical Co., Ltd. | Rho-associated protein kinase inhibitor, pharmaceutical composition comprising the same, as well as preparation method and use thereof |
| CN117343049A (zh) | 2017-06-30 | 2024-01-05 | 北京泰德制药股份有限公司 | Rho相关蛋白激酶抑制剂、包含其的药物组合物及其制备方法和用途 |
| CN116589461A (zh) * | 2017-08-23 | 2023-08-15 | 思普瑞特生物科学公司 | 氮杂吲哚基吡啶酮化合物和二氮杂吲哚基吡啶酮化合物 |
| CN109535164B (zh) * | 2017-09-21 | 2022-01-18 | 上海华汇拓医药科技有限公司 | Jak激酶抑制剂及其制备方法和在医药领域的应用 |
| AU2018360059B2 (en) | 2017-11-03 | 2023-07-13 | Aclaris Therapeutics, Inc. | Substituted pyrrolopyrimidine JAK inhibitors and methods of making and using the same |
| WO2019090143A1 (en) * | 2017-11-03 | 2019-05-09 | Aclaris Therapeutics, Inc. | Pyrazolyl pyrrolo[2,3-b]pyrimidine-5-carboxylate analogs and methods of making the same |
| TW201924683A (zh) | 2017-12-08 | 2019-07-01 | 美商英塞特公司 | 用於治療骨髓增生性贅瘤的低劑量組合療法 |
| PL3746429T3 (pl) | 2018-01-30 | 2022-06-20 | Incyte Corporation | Procesy do otrzymywania (1-(3-fluoro-2-(trifluorometylo)izonikotynoilo)piperydyn-4-onu) |
| EP3768661B1 (en) * | 2018-03-23 | 2024-05-01 | Fochon Pharmaceuticals, Ltd. | Deuterated compounds as rock inhibitors |
| RS65624B1 (sr) | 2018-03-30 | 2024-07-31 | Incyte Corp | Lečenje supurativnog hidradenitisa upotrebom jak inhbitora |
| BR112021002479A2 (pt) | 2018-08-10 | 2021-07-27 | Aclaris Therapeutics, Inc. | composto, composição farmacêutica, método para inibir a atividade de itk ou jak3 em uma população de células, método para tratar um distúrbio mediado por itk ou jak3 em um indivíduo necessitando do mesmo e uso de um composto |
| WO2020081689A1 (en) | 2018-10-16 | 2020-04-23 | Dana-Farber Cancer Institute, Inc. | Azaindole inhibitors of wild-type and mutant forms of lrrk2 |
| JP7564983B2 (ja) | 2019-01-18 | 2024-10-10 | ボロノイ インコーポレイテッド | ピロロピリジン誘導体およびタンパク質キナーゼ関連疾患の予防または治療での使用のためのその用途 |
| EP3947737A2 (en) | 2019-04-02 | 2022-02-09 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods of predicting and preventing cancer in patients having premalignant lesions |
| EP3955920A1 (en) | 2019-04-16 | 2022-02-23 | Institut National de la Santé et de la Recherche Médicale (INSERM) | Use of jak inhibitors for the treatment of painful conditions involving nav1.7 channels |
| CA3138544A1 (en) * | 2019-05-02 | 2020-11-05 | Aclaris Therapeutics, Inc. | Substituted pyrrolopyridines as jak inhibitors |
| US20220252599A1 (en) * | 2019-07-12 | 2022-08-11 | The Johns Hopkins University | Compositions and methods for treating cerebral vasospasm |
| CA3156007A1 (en) | 2019-09-27 | 2021-04-01 | Disc Medicine, Inc. | METHODS OF TREATING MYELOFIBROSE AND ASSOCIATED CONDITIONS |
| PH12022551052A1 (en) | 2019-11-22 | 2023-05-29 | Incyte Corp | Combination therapy comprising an alk2 inhibitor and a jak2 inhibitor |
| KR20230012539A (ko) | 2020-05-13 | 2023-01-26 | 디스크 메디슨, 인크. | 골수섬유증을 치료하기 위한 항-헤모주벨린 (hjv) 항체 |
| EP3915990A1 (en) * | 2020-05-26 | 2021-12-01 | Centre National de la Recherche Scientifique | 4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-3,6-dihydropyridine-1-(2h)-carboxamide derivatives as limk and/or rock kinases inhibitors for use in the treatment of cancer |
| US11833155B2 (en) | 2020-06-03 | 2023-12-05 | Incyte Corporation | Combination therapy for treatment of myeloproliferative neoplasms |
| US10988479B1 (en) | 2020-06-15 | 2021-04-27 | G1 Therapeutics, Inc. | Morphic forms of trilaciclib and methods of manufacture thereof |
| KR20220081631A (ko) | 2020-12-09 | 2022-06-16 | 보로노이 주식회사 | 염증성 질환의 예방 및/또는 치료를 위한 피롤로-피리딘 유도체 화합물의 신규 용도 |
| CN113402523B (zh) * | 2021-07-13 | 2022-07-12 | 西安交通大学 | 一种靶向肥大细胞MrgX2小分子荧光探针及制备方法和应用 |
| CN113735859A (zh) * | 2021-08-12 | 2021-12-03 | 安徽医科大学 | 一种激酶抑制剂 |
| US20250109093A1 (en) | 2022-01-28 | 2025-04-03 | Nippon Soda Co., Ltd. | Method for producing amide compound |
| CN117050075A (zh) * | 2022-05-05 | 2023-11-14 | 中国药科大学 | 一类联芳环类bet抑制剂及合成方法与用途 |
| WO2023222565A1 (en) | 2022-05-16 | 2023-11-23 | Institut National de la Santé et de la Recherche Médicale | Methods for assessing the exhaustion of hematopoietic stems cells induced by chronic inflammation |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU95122760A (ru) * | 1993-03-01 | 1998-02-10 | Мерк Шарп Энд Домэ Лимитед | Пирроло-пиридиновые производные, способ их получения, фармкомпозиция на их основе, применение и способ лечения |
| WO2004099205A1 (en) * | 2003-05-09 | 2004-11-18 | Astrazeneca Ab | Azaindole compounds as kinase inhibitors |
Family Cites Families (55)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5304121A (en) | 1990-12-28 | 1994-04-19 | Boston Scientific Corporation | Drug delivery system making use of a hydrogel polymer coating |
| US5994341A (en) | 1993-07-19 | 1999-11-30 | Angiogenesis Technologies, Inc. | Anti-angiogenic Compositions and methods for the treatment of arthritis |
| US6099562A (en) | 1996-06-13 | 2000-08-08 | Schneider (Usa) Inc. | Drug coating with topcoat |
| PE20010306A1 (es) * | 1999-07-02 | 2001-03-29 | Agouron Pharma | Compuestos de indazol y composiciones farmaceuticas que los contienen utiles para la inhibicion de proteina kinasa |
| AP1917A (en) | 1999-12-24 | 2008-11-12 | Aventis Pharma Ltd | Azaindoles |
| WO2001081345A1 (en) * | 2000-04-20 | 2001-11-01 | Mitsubishi Pharma Corporation | Aromatic amide compounds |
| US6335342B1 (en) * | 2000-06-19 | 2002-01-01 | Pharmacia & Upjohn S.P.A. | Azaindole derivatives, process for their preparation, and their use as antitumor agents |
| MX242553B (es) | 2000-10-20 | 2006-12-06 | Eisai Co Ltd | Derivados aromaticos que contienen nitrogeno. |
| GB0115109D0 (en) * | 2001-06-21 | 2001-08-15 | Aventis Pharma Ltd | Chemical compounds |
| GB0202679D0 (en) | 2002-02-05 | 2002-03-20 | Glaxo Group Ltd | Novel compounds |
| US7304061B2 (en) * | 2002-04-26 | 2007-12-04 | Vertex Pharmaceuticals Incorporated | Heterocyclic inhibitors of ERK2 and uses thereof |
| DE50304983D1 (de) | 2002-10-28 | 2006-10-19 | Bayer Healthcare Ag | Heteroaryloxy-substituierte phenylaminopyrimidine als rho-kinaseinhibitoren |
| GB0227240D0 (en) * | 2002-11-21 | 2002-12-31 | Glaxo Group Ltd | Compounds |
| US7226919B2 (en) | 2002-12-18 | 2007-06-05 | Vertex Pharmaceuticals Inc. | Compositions useful as inhibitors of protein kinases |
| EP1611125A1 (en) | 2003-02-07 | 2006-01-04 | Vertex Pharmaceuticals Incorporated | Heteroaryl substituted pyrolls useful as inhibitors of protein kinases |
| JP2006517966A (ja) * | 2003-02-14 | 2006-08-03 | ワイス | ５−ヒドロキシトリプタミン−６リガンドとしてのヘテロサイクリル−３−スルホニルアザインドールまたは−アザインダゾール誘導体 |
| US7531553B2 (en) * | 2003-03-21 | 2009-05-12 | Amgen Inc. | Heterocyclic compounds and methods of use |
| FR2857661B1 (fr) * | 2003-07-15 | 2006-09-22 | Snc Eurokera | Produit en vitroceramique avec joint(s) de soudure; fabrication |
| US20050043346A1 (en) | 2003-08-08 | 2005-02-24 | Pharmacia Italia S.P.A. | Pyridylpyrrole derivatives active as kinase inhibitors |
| AR045595A1 (es) | 2003-09-04 | 2005-11-02 | Vertex Pharma | Composiciones utiles como inhibidores de proteinas quinasas |
| FR2861729B1 (fr) * | 2003-10-31 | 2006-09-08 | Fabre Pierre Dermo Cosmetique | Monomere d'alkyl-rhamnose ou d'alkyl-fucose, medicament comprenant un monomere d'alkyl-sucre reducteur |
| FR2862363B1 (fr) * | 2003-11-18 | 2007-01-26 | Antonov Automotive Europ | Dispositif de transmission a rapports multiples, notamment pour l'automobile |
| CN102786482A (zh) * | 2003-11-21 | 2012-11-21 | 阿雷生物药品公司 | Akt蛋白激酶抑制剂 |
| SI1696920T1 (sl) * | 2003-12-19 | 2015-02-27 | Plexxikon Inc. | Spojine in postopki za razvoj modulatorjev ret |
| BRPI0509369B1 (pt) | 2004-03-30 | 2021-08-03 | Vertex Pharmaceuticals Incorporated | Compostos azaindóis úteis como inibidores de jak e outras proteína cinases e composição farmacêutica |
| FR2868273B1 (fr) * | 2004-03-30 | 2006-07-07 | Parfums Christian Dior Sa | Presentoir d'articles tels que des produits cosmetiques |
| JP5019612B2 (ja) | 2004-04-02 | 2012-09-05 | 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 | Ｒｏｃｋの阻害剤として有用なアザインドールおよび他のプロテインキナーゼ |
| DE102004020570A1 (de) * | 2004-04-27 | 2005-11-24 | Bayer Healthcare Ag | Substituierte Phenylaminopyrimidine |
| ES2505090T3 (es) * | 2004-05-07 | 2014-10-09 | Amgen Inc. | Derivados heterocíclicos nitrogenados como moduladores de proteína cinasas y su uso para el tratamiento de angiogénesis y cáncer |
| US20060122213A1 (en) | 2004-06-30 | 2006-06-08 | Francoise Pierard | 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. |
| AU2005279795A1 (en) * | 2004-09-03 | 2006-03-09 | Plexxikon, Inc. | Bicyclic heteroaryl PDE4B inhibitors |
| FR2874920B1 (fr) * | 2004-09-09 | 2006-10-20 | Sanofi Aventis Sa | Derives de 3-spiro-indolin-2-one comme ligand des recepteurs de la vasopressine |
| MX2007003375A (es) | 2004-09-22 | 2007-05-07 | Janssen Pharmaceutica Nv | Inhibidores de la interaccion entre mdm2 y p53. |
| EP1812439B2 (en) * | 2004-10-15 | 2017-12-06 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
| MY179032A (en) * | 2004-10-25 | 2020-10-26 | Cancer Research Tech Ltd | Ortho-condensed pyridine and pyrimidine derivatives (e.g.purines) as protein kinase inhibitors |
| UY29177A1 (es) * | 2004-10-25 | 2006-05-31 | Astex Therapeutics Ltd | Derivados sustituidos de purina, purinona y deazapurina, composiciones que los contienen métodos para su preparación y sus usos |
| DK1812440T3 (da) | 2004-11-04 | 2011-01-31 | Vertex Pharma | Pyrazolo[1,5-a]pyrimidiner, der kan anvendes som inhibistorer af proteinkinaser |
| WO2006052568A2 (en) * | 2004-11-10 | 2006-05-18 | Eli Lilly And Company | Tgf-beta inhibitors |
| US7795259B2 (en) | 2004-11-22 | 2010-09-14 | Vertex Pharmaceuticals Incorporated | Pyrrolopyrazines and pyrazolopyrazines useful as inhibitors of protein kinases |
| AR054416A1 (es) * | 2004-12-22 | 2007-06-27 | Incyte Corp | Pirrolo [2,3-b]piridin-4-il-aminas y pirrolo [2,3-b]pirimidin-4-il-aminas como inhibidores de las quinasas janus. composiciones farmaceuticas. |
| CA2590261C (en) * | 2004-12-27 | 2011-08-16 | Alcon, Inc. | Aminopyrazine analogs for treating glaucoma and other rho kinase-mediated diseases and conditions |
| GB0501999D0 (en) * | 2005-02-01 | 2005-03-09 | Sentinel Oncology Ltd | Pharmaceutical compounds |
| CA2596830A1 (en) | 2005-02-03 | 2006-09-14 | Vertex Pharmaceuticals Incorporated | Pyrrolopyrimidines useful as inhibitors of protein kinase |
| WO2006124863A2 (en) * | 2005-05-16 | 2006-11-23 | Irm Llc | Pyrrolopyridine derivatives as protein kinase inhibitors |
| ZA200710379B (en) * | 2005-05-20 | 2009-05-27 | Vertex Pharma | Pyrrolopyridines useful as inhibitors of protein kinase |
| CN101801971A (zh) | 2005-09-30 | 2010-08-11 | 沃泰克斯药物股份有限公司 | 可用作janus激酶抑制剂的脱氮嘌呤 |
| CN102532133A (zh) | 2006-01-17 | 2012-07-04 | 沃泰克斯药物股份有限公司 | 适用作詹纳斯激酶抑制剂的吖吲哚类 |
| WO2007084667A2 (en) * | 2006-01-19 | 2007-07-26 | Osi Pharmaceutical, Inc. | Fused heterobicyclic kinase inhibitors |
| RU2008143361A (ru) | 2006-04-05 | 2010-05-10 | Вертекс Фармасьютикалз Инкорпорейтед (Us) | Деазапурины в качестве ингибиторов янус-киназ |
| AR064675A1 (es) | 2006-12-21 | 2009-04-15 | Vertex Pharma | Derivados heterociclicos de pirrolo- [2,3-b] piridina, inhibidores de proteinquinasas plk, composiciones farmaceuticas que los contienen, proceso de preparacion y uso de los mismos en trastornos hiperproliferativos |
| JP2009123635A (ja) * | 2007-11-19 | 2009-06-04 | Nissan Diesel Motor Co Ltd | ハーネス組立体 |
| UY32717A (es) | 2009-06-17 | 2011-01-31 | Vertex Pharma | Inhibidores de la replicación de virus de la gripe |
| CN103562205A (zh) | 2010-12-16 | 2014-02-05 | 沃泰克斯药物股份有限公司 | 流感病毒复制的抑制剂 |
| UA118010C2 (uk) | 2011-08-01 | 2018-11-12 | Вертекс Фармасьютікалз Інкорпорейтед | Інгібітори реплікації вірусів грипу |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU95122760A (ru) * | 1993-03-01 | 1998-02-10 | Мерк Шарп Энд Домэ Лимитед | Пирроло-пиридиновые производные, способ их получения, фармкомпозиция на их основе, применение и способ лечения |
| WO2004099205A1 (en) * | 2003-05-09 | 2004-11-18 | Astrazeneca Ab | Azaindole compounds as kinase inhibitors |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2634723C2 (ru) * | 2013-04-02 | 2017-11-03 | Ф. Хоффманн-Ля Рош Аг | Ингибиторы тирозинкиназы брутона |
| RU2649575C1 (ru) * | 2014-02-04 | 2018-04-04 | Тайхо Фармасьютикал Ко., Лтд. | Азаиндольное производное |
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| AU2006251623A1 (en) | 2006-11-30 |
| JP2013253114A (ja) | 2013-12-19 |
| EP1881983A1 (en) | 2008-01-30 |
| RU2011133825A (ru) | 2013-02-20 |
| WO2006127587A1 (en) | 2006-11-30 |
| CN101228161B (zh) | 2012-10-10 |
| JP2008545660A (ja) | 2008-12-18 |
| CN101228161A (zh) | 2008-07-23 |
| RU2007147455A (ru) | 2009-06-27 |
| EP1881983B1 (en) | 2012-01-11 |
| US20070135466A1 (en) | 2007-06-14 |
| EP2354139A1 (en) | 2011-08-10 |
| ZA200710379B (en) | 2009-05-27 |
| ES2380795T3 (es) | 2012-05-18 |
| US8921376B2 (en) | 2014-12-30 |
| KR20080016659A (ko) | 2008-02-21 |
| ATE540948T1 (de) | 2012-01-15 |
| NZ564065A (en) | 2011-03-31 |
| MX2007014619A (es) | 2009-02-13 |
| EP2354140A1 (en) | 2011-08-10 |
| CA2609126A1 (en) | 2006-11-30 |
| NO20076502L (no) | 2008-02-19 |
| JP2009179644A (ja) | 2009-08-13 |
| IL187438A0 (en) | 2008-02-09 |
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