JP2013540158A - 結晶性（８Ｓ，９Ｒ）−５−フルオロ−８−（４−フルオロフェニル）−９−（１−メチル−１Ｈ−１，２，４−トリアゾール−５−イル）−８，９−ジヒドロ−２Ｈ−ピリド［４，３，２−ｄｅ］フタラジン−３（７Ｈ）−オントシレート塩 - Google Patents
結晶性（８Ｓ，９Ｒ）−５−フルオロ−８−（４−フルオロフェニル）−９−（１−メチル−１Ｈ−１，２，４−トリアゾール−５−イル）−８，９−ジヒドロ−２Ｈ−ピリド［４，３，２−ｄｅ］フタラジン−３（７Ｈ）−オントシレート塩 Download PDFInfo
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- JP2013540158A JP2013540158A JP2013535079A JP2013535079A JP2013540158A JP 2013540158 A JP2013540158 A JP 2013540158A JP 2013535079 A JP2013535079 A JP 2013535079A JP 2013535079 A JP2013535079 A JP 2013535079A JP 2013540158 A JP2013540158 A JP 2013540158A
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- pyrido
- methyl
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- fluorophenyl
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- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
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- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2014522877A (ja) * | 2011-08-11 | 2014-09-08 | バイエル・インテレクチユアル・プロパテイー・ゲー・エム・ベー・ハー | １，２，４−トリアゾリル置換されたケトエノール類 |
| JP2017523243A (ja) * | 2014-07-31 | 2017-08-17 | メディヴェイション テクノロジーズ， インコーポレーテッド | （２ｓ，３ｓ）−メチル ７−フルオロ−２−（４−フルオロフェニル）−３−（１−メチル−１ｈ−１，２，４−トリアゾール−５−イル）−４−オキソ−１，２，３，４−テトラヒドロキノリン−５−カルボキシレートの共形成剤塩、およびそれらを製造する方法 |
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| MX340319B (es) * | 2010-02-08 | 2016-07-06 | Medivation Technologies Inc | Procesos para sintetizar derivados de dihidropiridoftalazinona. |
| CN103282365B (zh) | 2010-10-21 | 2017-12-29 | 麦迪韦逊科技有限公司 | 结晶的(8S,9R)‑5‑氟‑8‑(4‑氟苯基)‑9‑(1‑甲基‑1H‑1,2,4‑三唑‑5‑基)‑8,9‑二氢‑2H‑吡啶并[4,3,2‑de]酞嗪‑3(7H)‑酮甲苯磺酸盐 |
| PT3406251T (pt) | 2011-05-03 | 2024-01-24 | Agios Pharmaceuticals Inc | Ativadores da piruvato-cinase para utilização em terapia |
| CN102827170A (zh) | 2011-06-17 | 2012-12-19 | 安吉奥斯医药品有限公司 | 治疗活性组合物和它们的使用方法 |
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| SMT202100444T1 (it) * | 2014-03-14 | 2021-09-14 | Les Laboratories Servier Sas | Composizioni farmaceutiche di composti terapeuticamente attivi |
| WO2016007722A1 (en) | 2014-07-10 | 2016-01-14 | Incyte Corporation | Triazolopyridines and triazolopyrazines as lsd1 inhibitors |
| EA201792205A1 (ru) | 2015-04-03 | 2018-02-28 | Инсайт Корпорейшн | Гетероциклические соединения как ингибиторы lsd1 |
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| US10284860B1 (en) * | 2018-07-02 | 2019-05-07 | Tencent America LLC | Method and apparatus for video coding |
| CN112424671B (zh) | 2018-07-13 | 2023-10-27 | 奇跃公司 | 用于显示双目变形补偿的系统和方法 |
| US10968200B2 (en) | 2018-08-31 | 2021-04-06 | Incyte Corporation | Salts of an LSD1 inhibitor and processes for preparing the same |
| US20210355223A1 (en) | 2018-11-05 | 2021-11-18 | Pfizer Inc. | Combinations for Treating Cancer |
| WO2021069700A1 (en) * | 2019-10-10 | 2021-04-15 | Myovant Sciences Gmbh | Crystalline solvated forms of n-(4-(1-(2,6-difluorobenzyl)-5- ((dimethylamino)methyl)-3-(6-methoxy-3-pyridazinyl)-2,4-dioxo-1,2,3,4- tetrahydrothieno[2,3-d]pyrimidin-6-yl)phenyl)-n'-methoxyurea |
| EP4118105A2 (en) | 2020-03-09 | 2023-01-18 | Pfizer Inc. | Cd80-fc fusion protein and uses thereof |
| JP2023548896A (ja) | 2020-11-13 | 2023-11-21 | ファイザー・インク | タラゾパリブ軟質ゼラチンカプセル剤形 |
| US20240052423A1 (en) | 2020-12-07 | 2024-02-15 | Pfizer Inc. | Methods of identifying a tumor that is sensitive to treatment with talazoparib and methods of treatment thereof |
| EP4313034A1 (en) | 2021-03-24 | 2024-02-07 | Pfizer Inc. | Combination of talazoparib and an anti-androgen for the treatment of ddr gene mutated metastatic castration-sensitive prostate cancer |
| WO2023131894A1 (en) | 2022-01-08 | 2023-07-13 | Pfizer Inc. | Genomic loss of heterozygosity as a predictive biomarker for treatment with talazoparib and methods of treatment thereof |
| WO2023201338A1 (en) | 2022-04-15 | 2023-10-19 | Ideaya Biosciences, Inc. | Combination therapy comprising a mat2a inhibitor and a parp inhibitor |
| EP4532493A1 (en) | 2022-06-01 | 2025-04-09 | Ideaya Biosciences, Inc. | Thiadiazolyl derivatives as dna polymerase theta inhibitors and uses thereof |
| TWI883565B (zh) | 2022-10-02 | 2025-05-11 | 美商輝瑞大藥廠 | 用於治療轉移性去勢抵抗性前列腺癌之他拉唑帕尼及恩雜魯胺之組合 |
| TW202425976A (zh) | 2022-12-17 | 2024-07-01 | 美商輝瑞大藥廠 | 用於治療轉移性去勢抵抗性前列腺癌之他拉唑帕尼及恩雜魯胺之組合 |
| TW202600137A (zh) | 2024-04-04 | 2026-01-01 | 美商輝瑞股份有限公司 | 於使用ｐａｒｐ抑制劑的治療作為預測性生物標記之ｔｍｐｒｓｓ２－ｅｒｇ和ｒｂｉ及使用ｐａｒｐ抑制劑之治療方法 |
| WO2026078619A1 (en) | 2024-10-09 | 2026-04-16 | Pfizer Inc. | Combination of talazoparib and enzalutamide in the treatment of metastatic castration-resistant prostate cancer |
| WO2026078615A1 (en) | 2024-10-09 | 2026-04-16 | Pfizer Inc. | Combination of talazoparib and enzalutamide in the treatment of metastatic castration-resistant prostate cancer |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100035883A1 (en) * | 2008-08-06 | 2010-02-11 | Lead Therapeutics, Inc. | Dihydropyridophthalazinone inhibitors of poly(adp-ribose)polymerase (parp) |
Family Cites Families (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4415504A (en) | 1981-09-21 | 1983-11-15 | Tanabe Seiyaku Co., Ltd. | p-Hydroxyphenylglycine.α-phenylethanesulfonate, process for production thereof and utilization thereof in resolution of p-hydroxyphenylglycine |
| JPS58225065A (ja) | 1982-06-21 | 1983-12-27 | Nippon Shinyaku Co Ltd | ２−キノロン誘導体 |
| US5328905A (en) | 1987-07-20 | 1994-07-12 | Duphar International Research B.V. | 8,9-anellated-1,2,3,4-tetrahydro-β-carboline derivatives |
| GB9505538D0 (en) | 1995-03-18 | 1995-05-03 | Ciba Geigy Ag | New compounds |
| ID19155A (id) | 1996-12-13 | 1998-06-18 | Tanabe Seiyaku Co | Turunan-turunan piridin, pembuatannya dan intermediet untuk pembuatannya |
| DE19727410A1 (de) | 1997-06-27 | 1999-01-07 | Hoechst Schering Agrevo Gmbh | 3-(5-Tetrazolylcarbonyl)-2-chinolone und diese enthaltende nutzpflanzenschützende Mittel |
| US6514983B1 (en) | 1997-09-03 | 2003-02-04 | Guilford Pharmaceuticals Inc. | Compounds, methods and pharmaceutical compositions for treating neural or cardiovascular tissue damage |
| TW430656B (en) | 1997-12-03 | 2001-04-21 | Dainippon Ink & Chemicals | Quinolinone derivative, method for preparing the same, and anti-allergic agent |
| CA2332239A1 (en) | 1998-05-15 | 1999-11-25 | Guilford Pharmaceuticals Inc. | Fused tricyclic compounds which inhibit parp activity |
| DE19921567A1 (de) | 1999-05-11 | 2000-11-16 | Basf Ag | Verwendung von Phthalazine-Derivaten |
| JP2001302669A (ja) | 2000-04-18 | 2001-10-31 | Meiji Seika Kaisha Ltd | 三環性フタラジノン誘導体 |
| JP2002284699A (ja) | 2001-03-28 | 2002-10-03 | Sumitomo Pharmaceut Co Ltd | 視細胞変性疾患治療剤 |
| AR036081A1 (es) | 2001-06-07 | 2004-08-11 | Smithkline Beecham Corp | Compuesto de 1,2-dihidroquinolina, su uso para preparar una composicion farmaceutica, metodos para prepararlo y compuestos del acido 2-aminobenzoico n-alquilado de utilidad como intermediarios en dichos metodos |
| SE0102315D0 (sv) | 2001-06-28 | 2001-06-28 | Astrazeneca Ab | Compounds |
| KR100663147B1 (ko) * | 2002-02-19 | 2007-02-28 | 오노 야꾸힝 고교 가부시키가이샤 | 축합 피리다진 유도체 화합물 및 이를 유효 성분으로서함유하는 약제 |
| EP1340819A1 (en) | 2002-02-28 | 2003-09-03 | Institut National De La Sante Et De La Recherche Medicale (Inserm) | Microsatellite markers |
| GB0221443D0 (en) | 2002-09-16 | 2002-10-23 | Glaxo Group Ltd | Pyridine derivates |
| EP1400244A1 (en) | 2002-09-17 | 2004-03-24 | Warner-Lambert Company LLC | New spirocondensed quinazolinones and their use as phosphodiesterase inhibitors |
| AU2003277674A1 (en) | 2002-11-12 | 2004-06-03 | Mochida Pharmaceutical Co., Ltd. | Novel parp inhibitors |
| PL1633724T3 (pl) | 2003-03-12 | 2011-10-31 | Kudos Pharm Ltd | Pochodne ftalazynonu |
| EP1633362B1 (en) | 2003-05-28 | 2012-09-26 | Eisai Inc. | Compounds, methods and pharmaceutical compositions for inhibiting parp |
| WO2005080356A1 (en) | 2004-02-18 | 2005-09-01 | Astrazeneca Ab | Tetrazole compounds and their use as metabotropic glutamate receptor antagonits |
| GB0612971D0 (en) | 2006-06-30 | 2006-08-09 | Angeletti P Ist Richerche Bio | Therapeutic compounds |
| US8198448B2 (en) | 2006-07-14 | 2012-06-12 | Amgen Inc. | Fused heterocyclic derivatives and methods of use |
| EA015952B1 (ru) | 2007-05-03 | 2011-12-30 | Пфайзер Лимитед | 2-пиридинкарбоксамидные производные в качестве модуляторов натриевых каналов |
| WO2010017850A1 (de) | 2008-08-12 | 2010-02-18 | Boehringer Ingelheim International Gmbh | Verfahren zur herstellung von cycloalkyl-substituierten piperazinverbindungen |
| BRPI0721950A2 (pt) | 2007-08-22 | 2015-09-29 | 4Sc Ag | indolopiridinas como inibidores da proteína de fuso de cinesina |
| CN101998959B (zh) | 2008-02-06 | 2013-08-28 | 生物马林药物股份有限公司 | 聚(adp-核糖)聚合酶(parp)的苯并噁唑甲酰胺抑制剂 |
| CA2787844C (en) | 2010-02-03 | 2019-08-27 | Biomarin Pharmaceutical Inc. | Dihydropyridophthalazinone inhibitors of poly(adp-ribose) polymerase (parp) for use in treatment of diseases associated with a pten deficiency |
| US20110190266A1 (en) | 2010-02-04 | 2011-08-04 | Daniel Chu | 5,6,6a,7,8,9-HEXAHYDRO-2H-PYRIDOPHTHALAZINONE INHIBITORS OF POLY(ADP-RIBOSE)POLYMERASE (PARP) |
| MX340319B (es) | 2010-02-08 | 2016-07-06 | Medivation Technologies Inc | Procesos para sintetizar derivados de dihidropiridoftalazinona. |
| WO2011130661A1 (en) | 2010-04-16 | 2011-10-20 | Biomarin Pharmaceutical Inc. | Methods of using dihydropyridophthalazinone inhibitors of poly (adp-ribose)polymerase (parp) |
| WO2011140009A1 (en) | 2010-05-04 | 2011-11-10 | Biomarin Pharmaceutical Inc. | Methods of using semi-synthetic glycopeptides as antibacterial agents |
| CN103282365B (zh) | 2010-10-21 | 2017-12-29 | 麦迪韦逊科技有限公司 | 结晶的(8S,9R)‑5‑氟‑8‑(4‑氟苯基)‑9‑(1‑甲基‑1H‑1,2,4‑三唑‑5‑基)‑8,9‑二氢‑2H‑吡啶并[4,3,2‑de]酞嗪‑3(7H)‑酮甲苯磺酸盐 |
| WO2012166151A1 (en) | 2011-06-03 | 2012-12-06 | Biomarin Pharmaceutical Inc. | Use of dihydropyridophthalazinone inhibitors of poly (adp-ribose) polymerase (parp) in the treatment of myelodysplastic syndrome (mds) and acute myeloid leukaemia (aml) |
| WO2013028495A1 (en) | 2011-08-19 | 2013-02-28 | Biomarin Pharmaceutical Inc. | Dihydropyridophthalazinone inhibitors of poly (adp-ribose) polymerase (parp) for the treatment of multiple myeloma |
| US20130053365A1 (en) | 2011-08-30 | 2013-02-28 | Biomarin Pharmaceutical, Inc. | Dihydropyridophthalazinone inhibitors of poly(adp-ribose)polymerase (parp) |
| EP3066084A1 (en) | 2013-11-07 | 2016-09-14 | Medivation Technologies, Inc. | Triazole intermediates useful in the synthesis of protected n-alkyltriazolecarbaldehydes |
| EA201790290A1 (ru) | 2014-07-31 | 2017-07-31 | Медивэйшн Текнолоджиз, Инк. | Формерные соли (2s,3s)-метил 7-фтор-2-(4-фторфенил)-3-(1-метил-1h-1,2,4-триазол-5-ил)-4-оксо-1,2,3,4-тетрагидрохинолин-5-карбоксилата и способы их получения |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100035883A1 (en) * | 2008-08-06 | 2010-02-11 | Lead Therapeutics, Inc. | Dihydropyridophthalazinone inhibitors of poly(adp-ribose)polymerase (parp) |
Non-Patent Citations (6)
| Title |
|---|
| BASTIN,R.J. ET AL: "Salt selection and optimization procedures for pharmaceutical new chemical entities", ORGANIC PROCESS RESEARCH & DEVELOPMENT, vol. 4, no. 5, JPN6009059058, 2000, pages 427 - 435, ISSN: 0003146184 * |
| BAUER J.F.: "Polymorphysm-A Critical Consideration in Pharmaceutical Development Manufacturing, and Stability", JOURNAL OF VALIDATION TECHNOLOGY, JPN6015034900, 2008, pages 15 - 23, ISSN: 0003146187 * |
| JOURNAL OF PHARMACEUTICAL SCIENCES, vol. 66, no. 1, JPN6014023656, 1977, pages 1 - 19, ISSN: 0003146183 * |
| 小嶌隆史: "医薬品開発における結晶性選択の効率化を目指して", 薬剤学, vol. 68, no. 5, JPN6009053757, 1 September 2008 (2008-09-01), pages 344 - 349, ISSN: 0003146186 * |
| 長瀬博監訳, 最新 創薬化学 下巻, JPN6008054607, 25 September 1999 (1999-09-25), JP, pages 347 - 365, ISSN: 0003146182 * |
| 高田則幸: "創薬段階における原薬Formスクリーニングと選択", PHARM STAGE, vol. 6, no. 10, JPN6009053755, 15 January 2007 (2007-01-15), pages 20 - 25, ISSN: 0003146185 * |
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