AU2008299896B2 - Tartrate salts or complexes of quinazoline based EGFR inhibitors containing a zinc binding moiety - Google Patents
Tartrate salts or complexes of quinazoline based EGFR inhibitors containing a zinc binding moiety Download PDFInfo
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- AU2008299896B2 AU2008299896B2 AU2008299896A AU2008299896A AU2008299896B2 AU 2008299896 B2 AU2008299896 B2 AU 2008299896B2 AU 2008299896 A AU2008299896 A AU 2008299896A AU 2008299896 A AU2008299896 A AU 2008299896A AU 2008299896 B2 AU2008299896 B2 AU 2008299896B2
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- tartaric acid
- mmol
- cyclodextrin
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/235—Saturated compounds containing more than one carboxyl group
- C07C59/245—Saturated compounds containing more than one carboxyl group containing hydroxy or O-metal groups
- C07C59/255—Tartaric acid
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/94—Nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Organic Chemistry (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Chemical Kinetics & Catalysis (AREA)
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| KR101434164B1 (ko) | 2006-09-11 | 2014-08-26 | 쿠리스 인코퍼레이션 | 아연 결합 부분을 함유한 퀴나졸린 계열 ｅｇｆｒ 억제제 |
| CN101570516B (zh) * | 2009-04-14 | 2011-01-05 | 重庆威尔德·浩瑞医药化工有限公司 | 一种制备4-(3-氯-4-氟苯基胺基)-7-甲氧基-6-[3-(4-吗啉基)丙氧基]喹唑啉的方法 |
| CN102452988B (zh) | 2010-10-27 | 2016-01-27 | 中国科学院化学研究所 | 一种喹唑啉衍生物及其制备方法 |
| CN103648500B (zh) | 2011-03-17 | 2016-05-04 | 宾夕法尼亚大学理事会 | 双功能酶制钳型分子的方法和用途 |
| US9295676B2 (en) | 2011-03-17 | 2016-03-29 | The Trustees Of The University Of Pennsylvania | Mutation mimicking compounds that bind to the kinase domain of EGFR |
| US20140229256A1 (en) | 2013-02-11 | 2014-08-14 | Solutran | Product substantiation using approved product list system and method |
| CN102276500A (zh) * | 2011-05-05 | 2011-12-14 | 西安交通大学 | 水杨酰胺类抗肿瘤化合物及其合成方法和用途 |
| KR20130047623A (ko) * | 2011-10-28 | 2013-05-08 | 주식회사종근당 | 신규한 선택적인 히스톤탈아세틸화 효소 억제제로서의 하이드록사메이트 유도체 및 이를 포함하는 약제학적 조성물 |
| WO2013159698A1 (zh) * | 2012-04-26 | 2013-10-31 | 深圳信立泰药业股份有限公司 | 稠环喹唑啉羟肟酸类化合物及其作为抗肿瘤药物的应用 |
| CN102898315B (zh) * | 2012-11-05 | 2015-01-28 | 上海毕得医药科技有限公司 | 3-乙炔基-4-氟苯胺的制备方法 |
| US10552861B2 (en) | 2013-02-11 | 2020-02-04 | Solutran, Inc. | Dual redemption path with shared benefits system and method |
| RU2017105844A (ru) * | 2014-08-08 | 2018-09-11 | Форсайт Вижн4, Инк. | Стабильные и растворимые составы ингибиторов рецепторных тирозинкиназ и способы их получения |
| CN105693630B (zh) * | 2016-03-10 | 2018-02-16 | 田静 | 一种吉非替尼中间体的制备方法 |
| WO2021044430A1 (en) * | 2019-09-08 | 2021-03-11 | Hadasit Medical Research Services And Development Ltd. | Anti-fibrotic compounds and use thereof |
| US12100049B2 (en) | 2020-06-05 | 2024-09-24 | Soltran, LLC | Filtered POS processing of services |
| EP4281449A1 (en) * | 2021-01-20 | 2023-11-29 | Lightox Limited | Protected hdac (histone deacetylase) inhibitors |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7230000B1 (en) * | 1999-10-27 | 2007-06-12 | Cytokinetics, Incorporated | Methods and compositions utilizing quinazolinones |
| AU2007296744A1 (en) * | 2006-09-11 | 2008-03-20 | Curis, Inc. | Multi-functional small molecules as anti-proliferative agents |
Family Cites Families (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5369108A (en) * | 1991-10-04 | 1994-11-29 | Sloan-Kettering Institute For Cancer Research | Potent inducers of terminal differentiation and methods of use thereof |
| AU661533B2 (en) * | 1992-01-20 | 1995-07-27 | Astrazeneca Ab | Quinazoline derivatives |
| CA2124306C (en) * | 1993-05-26 | 2004-04-06 | Masami Muraoka | Quinazolinone derivatives |
| GB9508537D0 (en) * | 1995-04-27 | 1995-06-14 | Zeneca Ltd | Quinazoline derivatives |
| GB9508538D0 (en) * | 1995-04-27 | 1995-06-14 | Zeneca Ltd | Quinazoline derivatives |
| US5747498A (en) * | 1996-05-28 | 1998-05-05 | Pfizer Inc. | Alkynyl and azido-substituted 4-anilinoquinazolines |
| JP4471404B2 (ja) * | 1996-02-13 | 2010-06-02 | アストラゼネカ ユーケイ リミテッド | Ｖｅｇｆインヒビターとしてのキナゾリン誘導体 |
| US6777217B1 (en) * | 1996-03-26 | 2004-08-17 | President And Fellows Of Harvard College | Histone deacetylases, and uses related thereto |
| IL144745A0 (en) | 1999-02-10 | 2002-06-30 | Astrazeneca Ab | Quinazoline derivatives as angiogenesis inhibitors |
| UA74803C2 (uk) * | 1999-11-11 | 2006-02-15 | Осі Фармасьютікалз, Інк. | Стійкий поліморф гідрохлориду n-(3-етинілфеніл)-6,7-біс(2-метоксіетокси)-4-хіназолінаміну, спосіб його одержання (варіанти) та фармацевтичне застосування |
| TWI310684B (en) * | 2000-03-27 | 2009-06-11 | Bristol Myers Squibb Co | Synergistic pharmaceutical kits for treating cancer |
| CA2439143A1 (en) | 2001-02-26 | 2002-09-06 | Mcgill University | Combi-molecules having signal transduction inhibitory properties and dna damaging properties |
| AU2003257666A1 (en) * | 2002-08-23 | 2004-03-11 | Kirin Beer Kabushiki Kaisha | COMPOUND HAVING TGFss INHIBITORY ACTIVITY AND MEDICINAL COMPOSITION CONTAINING THE SAME |
| US7250514B1 (en) * | 2002-10-21 | 2007-07-31 | Takeda San Diego, Inc. | Histone deacetylase inhibitors |
| CA2514479A1 (en) * | 2003-01-23 | 2004-08-05 | T.K. Signal Ltd. | Irreversible inhibitors of egf receptor tyrosine kinases and uses thereof |
| PE20040945A1 (es) * | 2003-02-05 | 2004-12-14 | Warner Lambert Co | Preparacion de quinazolinas substituidas |
| GB0322409D0 (en) | 2003-09-25 | 2003-10-29 | Astrazeneca Ab | Quinazoline derivatives |
| CA2540008A1 (en) * | 2003-09-25 | 2005-04-07 | Astrazeneca Ab | Quinazoline derivatives |
| WO2005097134A2 (en) | 2004-03-31 | 2005-10-20 | The Scripps Research Institute | Quinazoline based protein kinase inhibitors |
| EP2522397A1 (en) | 2005-02-03 | 2012-11-14 | TopoTarget UK Limited | Combination therapies using HDAC inhibitors |
| CN101198314A (zh) * | 2005-04-12 | 2008-06-11 | 伊兰制药国际有限公司 | 纳米微粒喹唑啉衍生物制剂 |
| AU2006236557A1 (en) | 2005-04-14 | 2006-10-26 | Novartis Vaccines And Diagnostics Inc. | 2-amino-quinazolin-5-ones as HSP90 inhibitors useful in treating proliferation diseases |
| ITMI20050729A1 (it) * | 2005-04-22 | 2006-10-23 | Endura Spa | Nuova formulazione biologicamente attiva |
| EP2018366A4 (en) | 2006-05-16 | 2010-08-04 | Univ Mcgill | HYBRID MOLECULES WITH MIXED VITAMIN D RECEPTOR AGONISM AND HISTONDEACETYLASE RESISTANT PROPERTIES |
| KR101434164B1 (ko) * | 2006-09-11 | 2014-08-26 | 쿠리스 인코퍼레이션 | 아연 결합 부분을 함유한 퀴나졸린 계열 ｅｇｆｒ 억제제 |
| US7547781B2 (en) | 2006-09-11 | 2009-06-16 | Curis, Inc. | Quinazoline based EGFR inhibitors containing a zinc binding moiety |
| CA2662587C (en) * | 2006-09-11 | 2013-08-06 | Curis, Inc. | Quinazoline based egfr inhibitors |
| CN101573333B (zh) | 2006-10-28 | 2013-06-12 | 梅特希尔基因公司 | 组蛋白脱乙酰酶抑制剂 |
| US8119616B2 (en) | 2007-09-10 | 2012-02-21 | Curis, Inc. | Formulation of quinazoline based EGFR inhibitors containing a zinc binding moiety |
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2008
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- 2008-03-10 WO PCT/US2008/056393 patent/WO2009035718A1/en not_active Ceased
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- 2008-03-10 AU AU2008299896A patent/AU2008299896B2/en not_active Ceased
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2010
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2013
- 2013-05-22 US US13/900,165 patent/US8846912B2/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7230000B1 (en) * | 1999-10-27 | 2007-06-12 | Cytokinetics, Incorporated | Methods and compositions utilizing quinazolinones |
| AU2007296744A1 (en) * | 2006-09-11 | 2008-03-20 | Curis, Inc. | Multi-functional small molecules as anti-proliferative agents |
Also Published As
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| HK1144532A1 (en) | 2011-02-25 |
| US20110053963A1 (en) | 2011-03-03 |
| AU2008299896A1 (en) | 2009-03-19 |
| CA2698944A1 (en) | 2009-03-19 |
| JP5474792B2 (ja) | 2014-04-16 |
| EP2190287A1 (en) | 2010-06-02 |
| US7846938B2 (en) | 2010-12-07 |
| US8846912B2 (en) | 2014-09-30 |
| WO2009035718A1 (en) | 2009-03-19 |
| CA2698944C (en) | 2015-06-16 |
| EP2190287A4 (en) | 2012-07-25 |
| JP2010539082A (ja) | 2010-12-16 |
| ES2526718T3 (es) | 2015-01-14 |
| EP2190287B1 (en) | 2014-10-29 |
| US20090076022A1 (en) | 2009-03-19 |
| US20130338167A1 (en) | 2013-12-19 |
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