JP2010523670A - Ｐｉ３ｋアルファのピリドピリミジノン阻害剤を使用した治療方法 - Google Patents
Ｐｉ３ｋアルファのピリドピリミジノン阻害剤を使用した治療方法 Download PDFInfo
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- JP2010523670A JP2010523670A JP2010503045A JP2010503045A JP2010523670A JP 2010523670 A JP2010523670 A JP 2010523670A JP 2010503045 A JP2010503045 A JP 2010503045A JP 2010503045 A JP2010503045 A JP 2010503045A JP 2010523670 A JP2010523670 A JP 2010523670A
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| EP1940839B1 (en) * | 2005-10-07 | 2013-07-31 | Exelixis, Inc. | PYRIDOPYRIMIDINONE INHIBITORS OF PI3Kalpha |
| ATE539752T1 (de) | 2006-08-16 | 2012-01-15 | Exelixis Inc | Verwendung von pi3k- und mek-modulatoren bei der krebsbehandlung |
| US8188113B2 (en) * | 2006-09-14 | 2012-05-29 | Deciphera Pharmaceuticals, Inc. | Dihydropyridopyrimidinyl, dihydronaphthyidinyl and related compounds useful as kinase inhibitors for the treatment of proliferative diseases |
| SA08280783B1 (ar) * | 2007-01-11 | 2011-04-24 | استرازينيكا ايه بي | مشتقات بيريدوبيريميدين كمثبطات pde4 |
| ES2430614T3 (es) | 2007-04-10 | 2013-11-21 | Exelixis, Inc. | Métodos de tratamiento del cáncer usando inhibidores de piridopirimidinona de PI3K alfa |
| RS53020B (sr) * | 2007-04-11 | 2014-04-30 | Exelixis Inc. | Kombinovane terapije koje sadrže hinoksalin inhibitor pi3k-alfa za upotrebu u lečenju kancera |
| JP5654990B2 (ja) | 2008-08-20 | 2015-01-14 | メルク・シャープ・アンド・ドーム・コーポレーションＭｅｒｃｋ Ｓｈａｒｐ ＆ Ｄｏｈｍｅ Ｃｏｒｐ． | アゾ置換ピリジンおよびピリミジン誘導体ならびにそれらのウイルス感染の治療における使用 |
| EP2326626B1 (en) * | 2008-08-20 | 2013-10-16 | Merck Sharp & Dohme Corp. | Ethenyl-substituted pyridine and pyrimidine derivatives and their use in treating viral infections |
| US8697694B2 (en) | 2008-08-20 | 2014-04-15 | Merck Sharp & Dohme Corp. | Substituted pyridine and pyrimidine derivatives and their use in treating viral infections |
| CA2734487A1 (en) | 2008-08-20 | 2010-02-25 | Southern Research Institute | Ethynyl-substituted pyridine and pyrimidine derivatives and their use in treating viral infections |
| AR080151A1 (es) | 2010-02-09 | 2012-03-14 | Exelixis Inc | Metodos para tratar cancer usando inhibidores de piridopirimidinona de pi 3k y mtor en combinacion con inhibidores de autofagia |
| WO2012027536A1 (en) * | 2010-08-26 | 2012-03-01 | Bristol-Myers Squibb Company | Combination of anti-ctla4 antibody with braf inhibitors for the synergistic treatment of proliferative diseases |
| AU2011302196B2 (en) | 2010-09-14 | 2016-04-28 | Exelixis, Inc. | Inhibitors of PI3K-delta and methods of their use and manufacture |
| WO2012065019A2 (en) | 2010-11-12 | 2012-05-18 | Exelixis, Inc. | Pyridopyrimidinone inhibitors of p13k alpha |
| WO2012158960A2 (en) * | 2011-05-17 | 2012-11-22 | H. Lee Moffitt Cancer Center & Research Institute, Inc. | Melanocortin 1 receptor ligands and methods of use |
| TW201306842A (zh) * | 2011-06-15 | 2013-02-16 | Exelixis Inc | 使用ｐｉ３ｋ／ｍｔｏｒ吡啶並嘧啶酮抑制劑及苯達莫司汀及／或利妥昔單抗治療惡性血液疾病之組合療法 |
| JP2014529298A (ja) * | 2011-07-28 | 2014-11-06 | ジェネンテック， インコーポレイテッド | Ｐｉｋ３ｃａｈ１０４７ｒノックイン非ヒト動物乳癌モデル |
| WO2013056067A1 (en) * | 2011-10-13 | 2013-04-18 | Exelixis, Inc. | Compounds for use in the treatment of basal cell carcinoma |
| AU2012332486A1 (en) | 2011-11-01 | 2014-06-19 | Arthur Decillis | N- (3- { [ (3- { [2-chloro-5- (methoxy) phenyl] amino} quinoxalin- 2 -yl) amino] sulfonyl} phe nyl) - 2 -methylalaninamide as phosphatidylinositol 3 - kinase inhibitor for the treatment of lymphoproliferative malignancies |
| CA2855666A1 (en) * | 2011-11-11 | 2013-05-16 | Intellikine, Llc | Combination of kinase inhibitors and uses thereof |
| US20150010545A1 (en) * | 2011-12-27 | 2015-01-08 | Kadmon Corporation, Llc | Methods for treatment of breast cancer nonresponsive to trastuzumab |
| US8461179B1 (en) | 2012-06-07 | 2013-06-11 | Deciphera Pharmaceuticals, Llc | Dihydronaphthyridines and related compounds useful as kinase inhibitors for the treatment of proliferative diseases |
| AU2013280644B2 (en) | 2012-06-26 | 2018-08-02 | Jeffrey A. BACHA | Methods for treating tyrosine-kinase-inhibitor-resistant malignancies in patients with genetic polymorphisms or AHI1 dysregulations or mutations employing dianhydrogalactitol, diacetyldianhydrogalactitol, dibromodulcitol, or analogs or derivatives thereof |
| US8980259B2 (en) * | 2012-07-20 | 2015-03-17 | Novartis Ag | Combination therapy |
| HK1211831A1 (zh) | 2012-08-07 | 2016-06-03 | Novartis Ag | 包含B-RAF抑制剂、EGFR抑制剂和任选PI3Kα抑制剂的药物组合 |
| JP2016519684A (ja) | 2013-04-08 | 2016-07-07 | デニス エム ブラウン | 準最適に投与された薬物療法の有効性を改善するための及び／又は副作用を低減するための方法および組成物 |
| US9950194B2 (en) | 2014-09-09 | 2018-04-24 | Mevion Medical Systems, Inc. | Patient positioning system |
| US11883404B2 (en) | 2016-03-04 | 2024-01-30 | Taiho Pharmaceuticals Co., Ltd. | Preparation and composition for treatment of malignant tumors |
| KR20180118719A (ko) | 2016-03-04 | 2018-10-31 | 다이호야쿠힌고교 가부시키가이샤 | 악성 종양 치료용 제제 및 조성물 |
| CN114394966B (zh) * | 2016-08-15 | 2024-10-11 | 辉瑞公司 | 吡啶并嘧啶酮cdk2/4/6抑制剂 |
| JP7027699B2 (ja) * | 2017-05-09 | 2022-03-02 | 住友ゴム工業株式会社 | タイヤトレッドおよびタイヤ |
| JP7523351B2 (ja) | 2018-01-31 | 2024-07-26 | デシフェラ・ファーマシューティカルズ，エルエルシー | 肥満細胞症の治療のための併用療法 |
| JP2021512105A (ja) | 2018-01-31 | 2021-05-13 | デシフェラ・ファーマシューティカルズ，エルエルシー | 消化管間質腫瘍の治療のための併用療法 |
| AU2019239404B2 (en) | 2018-03-19 | 2021-12-23 | Taiho Pharmaceutical Co., Ltd. | Pharmaceutical composition including sodium alkyl sulfate |
| NZ784949A (en) | 2019-08-12 | 2025-09-26 | Deciphera Pharmaceuticals Llc | Ripretinib for treating gastrointestinal stromal tumors |
| TWI878335B (zh) | 2019-08-12 | 2025-04-01 | 美商迪賽孚爾製藥有限公司 | 治療胃腸道基質瘤方法 |
| NZ789199A (en) | 2019-12-30 | 2025-07-25 | Deciphera Pharmaceuticals Llc | Compositions of 1-(4-bromo-5-(1-ethyl-7-(methylamino)-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2-fluorophenyl)-3-phenylurea |
| AU2020419197B2 (en) | 2019-12-30 | 2023-08-31 | Deciphera Pharmaceuticals, Llc | Amorphous kinase inhibitor formulations and methods of use thereof |
| KR102195221B1 (ko) | 2019-12-31 | 2020-12-24 | 서울대학교산학협력단 | 포스파티딜이노시톨 3-키나아제 억제제 및 프로그램화 세포 사멸 단백질 1 억제제를 포함하는, 삼중음성 유방암의 방사선 병용 치료용 약학적 조성물 |
| CN111358952B (zh) * | 2020-04-15 | 2022-03-15 | 中山大学肿瘤防治中心（中山大学附属肿瘤医院、中山大学肿瘤研究所） | 一种抗肿瘤药物组合物及其制剂和应用 |
| JP2024542205A (ja) * | 2021-11-18 | 2024-11-13 | オンコノヴァ セラピューティクス， インコーポレイテッド | がんを処置するための方法および組成物 |
| US11779572B1 (en) | 2022-09-02 | 2023-10-10 | Deciphera Pharmaceuticals, Llc | Methods of treating gastrointestinal stromal tumors |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008032162A1 (en) * | 2006-09-15 | 2008-03-20 | Pfizer Products Inc. | Pyrido (2, 3-d) pyrimidin0ne compounds and their use as pi3 inhibitors |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7019002B2 (en) * | 2001-12-11 | 2006-03-28 | Pharmacia & Upjohn, S.P.A. | Pyridopyrimidinones derivatives as telomerase inhibitors |
| US7576074B2 (en) * | 2002-07-15 | 2009-08-18 | Rice Kenneth D | Receptor-type kinase modulators and methods of use |
| CA2555724A1 (en) | 2004-02-18 | 2005-09-09 | Warner-Lambert Company Llc | 2-(pyridin-3-ylamino)-pyrido[2,3-d]pyrimidin-7-ones |
| DE602005002562T2 (de) * | 2004-05-04 | 2008-01-31 | Warner-Lambert Company Llc | Pyrrolylsubstituierte pyridoä2,3-düpyrimidin-7-one und derivate davon als therapeutische mittel |
| JP5216958B2 (ja) * | 2005-07-06 | 2013-06-19 | 株式会社三和技術総合研究所 | 漏洩電流検出装置及び漏洩電流検出方法 |
| EP1940839B1 (en) * | 2005-10-07 | 2013-07-31 | Exelixis, Inc. | PYRIDOPYRIMIDINONE INHIBITORS OF PI3Kalpha |
| JP5480503B2 (ja) | 2005-10-07 | 2014-04-23 | エクセリクシス， インク． | ＰＩ３Ｋαのピリドピリミジノン型阻害剤 |
| WO2007044729A2 (en) | 2005-10-07 | 2007-04-19 | Exelixis, Inc. | N- (3-amino-quinoxalin-2-yl) -sulfonamide derivatives and their use as phosphatidylinositol 3-kinase inhibitors |
| ATE539752T1 (de) | 2006-08-16 | 2012-01-15 | Exelixis Inc | Verwendung von pi3k- und mek-modulatoren bei der krebsbehandlung |
| ES2430614T3 (es) | 2007-04-10 | 2013-11-21 | Exelixis, Inc. | Métodos de tratamiento del cáncer usando inhibidores de piridopirimidinona de PI3K alfa |
| EP2142543B8 (en) | 2007-04-11 | 2013-07-03 | Exelixis, Inc. | Pyrido [2, 3-d]pyrimidin-7-one compounds as inhibitors of pi3k-alpha for the treatment of cancer |
| AU2008239596B2 (en) | 2007-04-11 | 2013-08-15 | Exelixis, Inc. | Pyrido [2,3-D] pyrimidin-7-one compounds as inhibitors of PI3K-alpha for the treatment of cancer |
| RS53020B (sr) | 2007-04-11 | 2014-04-30 | Exelixis Inc. | Kombinovane terapije koje sadrže hinoksalin inhibitor pi3k-alfa za upotrebu u lečenju kancera |
| EP2350070A1 (en) | 2008-09-30 | 2011-08-03 | Exelixis, Inc. | Pyridopyrimidinone inhibitors of pi3k and mtor |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008032162A1 (en) * | 2006-09-15 | 2008-03-20 | Pfizer Products Inc. | Pyrido (2, 3-d) pyrimidin0ne compounds and their use as pi3 inhibitors |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2023505690A (ja) * | 2019-12-10 | 2023-02-10 | ザ・トラスティーズ・オブ・インディアナ・ユニバーシティー | 複製タンパク質ａ（ｒｐａ）－ｄｎａ相互作用阻害剤 |
| JP7677646B2 (ja) | 2019-12-10 | 2025-05-15 | ザ・トラスティーズ・オブ・インディアナ・ユニバーシティー | 複製タンパク質ａ（ｒｐａ）－ｄｎａ相互作用阻害剤 |
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