JP2017520607A5 - - Google Patents
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- JP2017520607A5 JP2017520607A5 JP2017502247A JP2017502247A JP2017520607A5 JP 2017520607 A5 JP2017520607 A5 JP 2017520607A5 JP 2017502247 A JP2017502247 A JP 2017502247A JP 2017502247 A JP2017502247 A JP 2017502247A JP 2017520607 A5 JP2017520607 A5 JP 2017520607A5
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- Prior art keywords
- alkyl
- alkoxy
- independently
- cancer
- inhibitor
- Prior art date
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| ME03376B (me) | 2010-05-20 | 2020-01-20 | Array Biopharma Inc | Makrociklička jedinjenja kао inhibiтori trk kinaze |
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| JOP20190213A1 (ar) | 2017-03-16 | 2019-09-16 | Array Biopharma Inc | مركبات حلقية ضخمة كمثبطات لكيناز ros1 |
| CN109251181B (zh) * | 2017-07-13 | 2021-08-31 | 广东东阳光药业有限公司 | 取代脲衍生物的盐及其在药物中的应用 |
| CN109251182A (zh) * | 2017-07-13 | 2019-01-22 | 广东东阳光药业有限公司 | 取代脲衍生物的盐及其在药物中的应用 |
| CN109251183A (zh) * | 2017-07-13 | 2019-01-22 | 广东东阳光药业有限公司 | 取代脲衍生物的晶型及其在药物中的应用 |
| RU2764243C2 (ru) | 2017-09-22 | 2022-01-14 | ДЖУБИЛАНТ ЭПИПЭД ЭлЭлСи | Гетероциклические соединения в качестве ингибиторов PAD |
| TWI876442B (zh) | 2017-10-10 | 2025-03-11 | 美商絡速藥業公司 | 6-(2-羥基-2-甲基丙氧基)-4-(6-(6-((6-甲氧基吡啶-3-基)甲基)-3,6-二氮雜雙環[3.1.1]庚-3-基)吡啶-3-基)吡唑并[1,5-a]吡啶-3-甲腈之調配物 |
| TWI791053B (zh) | 2017-10-10 | 2023-02-01 | 美商亞雷生物製藥股份有限公司 | 6-(2-羥基-2-甲基丙氧基)-4-(6-(6-((6-甲氧基吡啶-3-基)甲基)-3,6-二氮雜雙環[3.1.1]庚-3-基)吡啶-3-基)吡唑并[1,5-a]吡啶-3-甲腈之結晶形式及其醫藥組合物 |
| KR20190043437A (ko) | 2017-10-18 | 2019-04-26 | 씨제이헬스케어 주식회사 | 단백질 키나제 억제제로서의 헤테로고리 화합물 |
| AU2018352142B2 (en) | 2017-10-18 | 2022-08-25 | Jubilant Epipad LLC | Imidazo-pyridine compounds as PAD inhibitors |
| US11629135B2 (en) | 2017-11-06 | 2023-04-18 | Jubilant Prodell Llc | Pyrimidine derivatives as inhibitors of PD1/PD-L1 activation |
| PT3704120T (pt) | 2017-11-24 | 2024-07-03 | Jubilant Episcribe Llc | Compostos heterocíclicos como inibidores de prmt5 |
| JP7060694B2 (ja) | 2018-01-18 | 2022-04-26 | アレイ バイオファーマ インコーポレイテッド | Ｒｅｔキナーゼ阻害剤としての置換ピロロ［２，３－ｄ］ピリミジン化合物 |
| EP3740490A1 (en) | 2018-01-18 | 2020-11-25 | Array Biopharma, Inc. | Substituted pyrazolo[3,4-d]pyrimidine compounds as ret kinase inhibitors |
| US11472802B2 (en) | 2018-01-18 | 2022-10-18 | Array Biopharma Inc. | Substituted pyrazolyl[4,3-c]pyridine compounds as RET kinase inhibitors |
| MX2020009517A (es) | 2018-03-13 | 2021-01-20 | Jubilant Prodel LLC | Compuestos biciclicos como inhibidores de la interaccion/activacio n de pdl/pd-l1. |
| CN108947982A (zh) * | 2018-08-16 | 2018-12-07 | 刘璐 | 治疗非酒精性脂肪肝病的吡嗪衍生物、组合物和应用 |
| PT3837256T (pt) | 2018-08-17 | 2023-05-23 | Novartis Ag | Compostos e composições de ureia como inibidores de smarca2/brm-atpase |
| CN112996794A (zh) | 2018-09-10 | 2021-06-18 | 阿雷生物药品公司 | 作为ret激酶抑制剂的稠合杂环化合物 |
| KR102195348B1 (ko) | 2018-11-15 | 2020-12-24 | 에이치케이이노엔 주식회사 | 단백질 키나제 억제제로서의 신규 화합물 및 이를 포함하는 약제학적 조성물 |
| KR102163889B1 (ko) * | 2019-01-11 | 2020-10-12 | 동의대학교 산학협력단 | 해죽순 추출물을 포함하는 신경병증성 통증 예방 및 치료용 조성물 |
| KR102217261B1 (ko) * | 2019-06-27 | 2021-02-17 | 한국생명공학연구원 | 척수성 근위축증 예방 또는 치료용 조성물 |
| CN112341378A (zh) * | 2019-08-06 | 2021-02-09 | 北京赛特明强医药科技有限公司 | 脲代炔基嘧啶或脲代炔基吡啶类化合物、及其组合物与应用 |
| CN118767143A (zh) | 2019-12-12 | 2024-10-15 | 听治疗有限责任公司 | 用于预防和治疗听力损失的组合物和方法 |
| KR102318032B1 (ko) * | 2020-02-20 | 2021-10-26 | 동의대학교 산학협력단 | 염증 및 신경병증성 통증의 예방 및 완화용 조성물 |
| CN117396473A (zh) * | 2021-03-17 | 2024-01-12 | 武田药品工业株式会社 | 血浆激肽释放酶的咪唑并吡啶基抑制剂 |
| MX2024008057A (es) | 2021-12-30 | 2024-08-28 | Biomea Fusion Inc | Compuestos de pirazina como inhibidores de flt3. |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9823873D0 (en) | 1998-10-30 | 1998-12-30 | Pharmacia & Upjohn Spa | 2-ureido-thiazole derivatives,process for their preparation,and their use as antitumour agents |
| JP2002539206A (ja) | 1999-03-12 | 2002-11-19 | ベーリンガー インゲルハイム ファーマシューティカルズ インコーポレイテッド | 抗炎症剤としての芳香族複素環化合物 |
| WO2003029209A2 (en) | 2001-10-02 | 2003-04-10 | Smithkline Beecham Corporation | Chemical compounds |
| EP1684762A4 (en) * | 2003-11-13 | 2009-06-17 | Ambit Biosciences Corp | UREA DERIVATIVES AS MODULATORS OF KINASE |
| ATE402705T1 (de) * | 2003-12-24 | 2008-08-15 | Astrazeneca Ab | Pyrimidine mit tie2 (tek) aktivität |
| DE602004018193D1 (de) | 2003-12-24 | 2009-01-15 | Astrazeneca Ab | Pyrimidine mit tie2 (tek) aktivität |
| MX2007000265A (es) * | 2004-07-02 | 2007-07-20 | Icos Corp | Compuestos utiles para inhibir chk1. |
| GB0502418D0 (en) * | 2005-02-05 | 2005-03-16 | Astrazeneca Ab | Compounds |
| DOP2006000051A (es) | 2005-02-24 | 2006-08-31 | Lilly Co Eli | Inhibidores de vegf-r2 y métodos |
| WO2007064931A2 (en) | 2005-12-02 | 2007-06-07 | Bayer Healthcare Llc | Substituted 4-amino-pyrrolotriazine derivatives useful for treating hyper-proliferative disorders and diseases associated with angiogenesis |
| EA034598B1 (ru) | 2005-12-23 | 2020-02-25 | Ариад Фармасьютикалз, Инк. | Применение бициклических гетероарильных соединений для лечения рака |
| KR101449057B1 (ko) | 2006-03-17 | 2014-10-10 | 암비트 바이오사이언시즈 코포레이션 | 질환 치료용 이미다졸로티아졸 화합물 |
| CN103435595A (zh) | 2006-05-08 | 2013-12-11 | 阿里亚德医药股份有限公司 | 炔类杂芳基化合物 |
| US8278307B2 (en) | 2006-05-08 | 2012-10-02 | Ariad Pharmaceuticals, Inc. | Monocyclic Heteroaryl compounds |
| EP2070929A1 (en) * | 2007-12-11 | 2009-06-17 | Bayer Schering Pharma Aktiengesellschaft | Alkynylaryl compounds and salts thereof, pharmaceutical compositions comprising same, methods of preparing same and uses of same |
| WO2009100536A1 (en) | 2008-02-15 | 2009-08-20 | Methylgene Inc. | Inhibitors of kinase activity with 1,2-di-cyclyl substituted alkyne structures |
| US9296722B2 (en) | 2010-05-27 | 2016-03-29 | Ambit Biosciences Corporation | Azolyl urea compounds and methods of use thereof |
| CN103172648B (zh) | 2011-12-20 | 2016-05-25 | 上海迪诺医药科技有限公司 | 三杂环衍生物、制备方法及应用 |
| US8877763B2 (en) * | 2012-03-22 | 2014-11-04 | Genosco | Substituted pyridopyrimidine compounds and their use as FLT3 inhibitors |
| CN103420977B (zh) | 2012-05-16 | 2016-06-22 | 上海医药集团股份有限公司 | 具有抗肿瘤活性的乙炔衍生物 |
| WO2015165085A1 (en) | 2014-04-30 | 2015-11-05 | F.Hoffmann-La Roche Ag | Morpholin-pyridine derivatives |
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