CA2679882C - Mitochondrial aldehyde dehydrogenase-2 modulators and methods of use thereof - Google Patents
Mitochondrial aldehyde dehydrogenase-2 modulators and methods of use thereof Download PDFInfo
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- CA2679882C CA2679882C CA2679882A CA2679882A CA2679882C CA 2679882 C CA2679882 C CA 2679882C CA 2679882 A CA2679882 A CA 2679882A CA 2679882 A CA2679882 A CA 2679882A CA 2679882 C CA2679882 C CA 2679882C
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- A—HUMAN NECESSITIES
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- A—HUMAN NECESSITIES
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
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- 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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| PCT/US2008/003092 WO2008112164A2 (en) | 2007-03-08 | 2008-03-07 | Mitochondrial aldehyde dehydrogenase-2 modulators and methods of use thereof |
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| WO (1) | WO2008112164A2 (OSRAM) |
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| CN101669030B (zh) | 2007-03-08 | 2016-01-13 | 小利兰·斯坦福大学托管委员会 | 线粒体醛脱氢酶2调节剂和其使用方法 |
| CN102209541B (zh) | 2008-09-08 | 2016-05-18 | 小利兰·斯坦福大学托管委员会 | 醛脱氢酶活性调节剂和其使用方法 |
| WO2010062308A1 (en) * | 2008-10-28 | 2010-06-03 | The Board Of Trustees Of The Leland Stanford Junior University | Modulators of aldehyde dehydrogenase and methods of use thereof |
| WO2012082862A2 (en) * | 2010-12-14 | 2012-06-21 | Beth Israel Deaconess Medical Center | Androgen receptor inhibitors and methods of use thereof |
| WO2012149106A1 (en) | 2011-04-29 | 2012-11-01 | The Board Of Trustees Of The Leland Stanford Junior University | Compositions and methods for increasing proliferation of adult salivary stem cells |
| TWI567061B (zh) | 2011-07-01 | 2017-01-21 | 吉李德科學股份有限公司 | 用於治療成癮之化合物 |
| US9545393B2 (en) * | 2012-08-24 | 2017-01-17 | The Board Of Trustees Of The Leland Stanford Junior University | Methods and compositions for treating pain |
| JP6410790B2 (ja) | 2013-03-14 | 2018-10-24 | ザ ボード オブ トラスティーズ オブ ザ レランド スタンフォード ジュニア ユニバーシティー | ミトコンドリアアルデヒドデヒドロゲナーゼ−２調節因子およびその使用方法 |
| CN103191103A (zh) * | 2013-04-15 | 2013-07-10 | 中南大学 | 乙醛脱氢酶激活物alda-1的合成方法及其用途 |
| CN103923077B (zh) * | 2013-07-05 | 2016-03-02 | 高尔医药科技(上海)有限公司 | 两种乙醛脱氢酶激动剂、其制备方法及用途 |
| JP6261278B2 (ja) * | 2013-10-16 | 2018-01-17 | 国立大学法人広島大学 | アルデヒドデヒドロゲナーゼの活性を増強するための医薬組成物 |
| WO2015084731A1 (en) * | 2013-12-02 | 2015-06-11 | The Board Of Trustees Of The Leland Stanford Junior University | Aldehyde dehydrogenase inhibitors and methods of use thereof |
| ES2833157T3 (es) * | 2014-02-19 | 2021-06-14 | Aviv Therapeutics Inc | Amidas políciclicas de unión a aldehído deshidrogenasa 2 mitocondrial (aldh2) y su uso para el tratamiento del cáncer |
| FR3054564B1 (fr) | 2016-07-28 | 2018-08-31 | Advanced Biodesign | Substrat specifique d'une isoenzyme de l'aldh |
| WO2019098288A1 (ja) * | 2017-11-15 | 2019-05-23 | 学校法人 慶應義塾 | 抗腫瘍剤及び配合剤 |
| US10406126B2 (en) | 2018-01-31 | 2019-09-10 | Eisai R&D Management Co., Ltd. | ALDH2 activator |
| CN108864034A (zh) * | 2018-06-04 | 2018-11-23 | 中国人民解放军第二军医大学 | 酰胺类醛脱氢酶激动剂、其合成方法及用途 |
| CN111909138A (zh) * | 2019-05-09 | 2020-11-10 | 上海仕谱生物科技有限公司 | 抑制tdg活性的化合物 |
| EP3973030A4 (en) * | 2019-05-23 | 2023-05-31 | Ekyj Consulting II, LLC | COMPOSITIONS AND METHODS FOR THE TREATMENT AND RELIEF OF ALCOHOLIC-INDUCED SKIN REMOVAL |
| CA3194020A1 (en) | 2020-11-02 | 2022-05-05 | Alchemedicine, Inc. | Compound, aldehyde dehydrogenase 2 activating agent, pharmaceutical composition, and therapeutic and/or prophylactic drug |
| EP4512468A1 (en) | 2022-04-22 | 2025-02-26 | Alchemedicine, Inc. | Compound, aldehyde dehydrogenase 2 activator, pharmaceutical composition, and treatment and/or preventative drug |
Family Cites Families (70)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2319808A (en) | 1939-08-31 | 1943-05-25 | Squibb & Sons Inc | Sterol derivatives and process for producing same |
| JPH01203351A (ja) | 1988-02-05 | 1989-08-16 | Mitsui Petrochem Ind Ltd | １，４−ジヒドロキシナフタレン誘導体および医薬 |
| JPH023351A (ja) | 1988-06-16 | 1990-01-08 | Oki Electric Ind Co Ltd | 印刷装置 |
| US4861891A (en) | 1988-08-31 | 1989-08-29 | Pfizer Inc. | Antidepressant N-substituted nicotinamide compounds |
| JPH03184973A (ja) | 1989-12-14 | 1991-08-12 | Rooman Kogyo:Kk | 放射線障害防護剤 |
| US5260323A (en) | 1990-06-28 | 1993-11-09 | Hoechst Aktiengesellschaft | 2,4- and 2,5-substituted pyridine-N-oxides, processes for their preparation and their use |
| DE4201047A1 (de) * | 1992-01-17 | 1993-07-22 | Bayer Ag | Substituierte isoxazolcarbonsaeureamide |
| US5272137A (en) * | 1992-02-14 | 1993-12-21 | Mcneil-Pfc, Inc. | Aqueous pharmaceutical suspension for pharmaceutical actives |
| JP2994182B2 (ja) | 1992-07-23 | 1999-12-27 | 石原産業株式会社 | アミド系化合物又はその塩、それらの製造方法及びそれらを含有する有害動物防除剤 |
| JP3833281B2 (ja) | 1995-02-03 | 2006-10-11 | 日本曹達株式会社 | ２，６−ジクロロイソニコチン酸ベンジルアミド誘導体及び植物病害防除剤 |
| EP1019385B1 (en) | 1995-09-15 | 2004-01-14 | PHARMACIA & UPJOHN COMPANY | Aminoaryl oxazolidinone n-oxides |
| US6072050A (en) | 1996-06-11 | 2000-06-06 | Pioneer Hi-Bred International, Inc. | Synthetic promoters |
| FR2751645B1 (fr) | 1996-07-29 | 1998-12-24 | Sanofi Sa | Amines pour la fabrication de medicaments destines a empecher la proliferation de cellules tumorales |
| CA2303848C (en) | 1997-10-31 | 2008-09-30 | Rhone-Poulenc Rorer Limited | Substituted anilides |
| WO1999032444A1 (en) | 1997-12-22 | 1999-07-01 | Eli Lilly And Company | Catalyst and method for amide formation |
| ATE234810T1 (de) * | 1998-04-20 | 2003-04-15 | Fujisawa Pharmaceutical Co | Anthranilsäurederivate als inhibitoren der c-gmp- phosphodiesterase |
| AR019190A1 (es) | 1998-07-08 | 2001-12-26 | Sod Conseils Rech Applic | Derivados de 2-aminopiridinas, productos intermedios para su preparacion, medicamentos y composiciones farmaceuticas que los contienen y su uso para preparar medicamentos |
| US6780883B2 (en) | 1998-11-05 | 2004-08-24 | Warner-Lambert Company | Amide inhibitors of microsomal triglyceride transfer protein |
| IL143332A0 (en) | 1998-11-25 | 2002-04-21 | Yissum Res Dev Co | Scavenger compounds |
| GB9919558D0 (en) | 1999-08-18 | 1999-10-20 | Hoechst Schering Agrevo Gmbh | Fungicidal compounds |
| AU1466001A (en) * | 1999-11-05 | 2001-05-14 | Phase-1 Molecular Toxicology | Methods of determining individual hypersensitivity to an agent |
| WO2001079489A2 (en) | 2000-04-18 | 2001-10-25 | Millennium Pharmaceuticals, Inc. | 39228, a human alcohol dehydrogenase and uses therefor |
| WO2002020500A2 (en) | 2000-09-01 | 2002-03-14 | Icos Corporation | Materials and methods to potentiate cancer treatment |
| WO2002022599A2 (en) | 2000-09-15 | 2002-03-21 | Anormed Inc. | Chemokine receptor binding heterocyclic compounds |
| US7141590B2 (en) | 2000-12-29 | 2006-11-28 | Ucb Sa | Pharmaceutical uses and synthesis of nicotinanilide-N-oxides |
| DOP2002000332A (es) | 2001-02-14 | 2002-08-30 | Warner Lambert Co | Inhibidores de piridina de metaloproteinasas de la matriz |
| US6678516B2 (en) | 2001-05-21 | 2004-01-13 | Nokia Corporation | Method, system, and apparatus for providing services in a privacy enabled mobile and Ubicom environment |
| US7547716B2 (en) | 2001-06-08 | 2009-06-16 | Institute Of Medicinal Molecular Design, Inc. | Sulfonamide derivatives |
| WO2003030937A1 (en) * | 2001-10-05 | 2003-04-17 | Ono Pharmaceutical Co., Ltd. | Remedies for stress diseases comprising mitochondrial benzodiazepine receptor antagonists |
| DE10149674A1 (de) | 2001-10-09 | 2003-04-24 | Apogepha Arzneimittel Gmbh | Orale Darreichungsformen für Propiverin oder seinen pharmazeutisch annehmbaren Salzen mit verlängerter Wirkstoffreisetzung |
| US20030100034A1 (en) | 2001-10-16 | 2003-05-29 | Millennium Pharmaceuticals, Inc. | 9136, a human aldehyde dehydrogenase family member and uses therefor |
| GB2400100B (en) | 2002-01-31 | 2006-04-12 | Pfizer Prod Inc | Metabolites of (3-{[4-tert-butyl-benzyl)-(pyridine-3-sulfonyl)-amino]-methyl}-phenoxy)-acetic acid |
| WO2003086377A1 (en) | 2002-04-18 | 2003-10-23 | Institute Of Medicinal Molecular Design. Inc. | Amide derivatives |
| GB0215650D0 (en) * | 2002-07-05 | 2002-08-14 | Cyclacel Ltd | Bisarylsufonamide compounds |
| WO2004022523A2 (en) | 2002-09-06 | 2004-03-18 | Elan Pharmaceuticals, Inc. | 1, 3-diamino-2-hydroxypropane prodrug derivatives |
| EP1402887A1 (en) * | 2002-09-18 | 2004-03-31 | Jerini AG | New compounds for the inhibition of undesired cell proliferation and use thereof |
| EP1402888A1 (en) * | 2002-09-18 | 2004-03-31 | Jerini AG | The use of substituted carbocyclic compounds as rotamases inhibitors |
| US7135575B2 (en) | 2003-03-03 | 2006-11-14 | Array Biopharma, Inc. | P38 inhibitors and methods of use thereof |
| US7022850B2 (en) | 2003-05-22 | 2006-04-04 | Bristol-Myers Squibb Co. | Bicyclicpyrimidones and their use to treat diseases |
| JP4359754B2 (ja) | 2003-07-03 | 2009-11-04 | 三菱瓦斯化学株式会社 | 基板の洗浄剤 |
| WO2005007889A1 (en) | 2003-07-21 | 2005-01-27 | Oncotherapy Science, Inc. | Method for diagnosing colorectal cancers |
| WO2005011561A2 (en) | 2003-08-04 | 2005-02-10 | Labcoat, Ltd. | Stent coating apparatus and method |
| GB0318814D0 (en) | 2003-08-11 | 2003-09-10 | Smithkline Beecham Corp | Novel compounds |
| FR2861074B1 (fr) | 2003-10-17 | 2006-04-07 | Sanofi Synthelabo | Derives de n-[phenyl(piperidin-2-yl)methyl]benzamide, leur preparation et leur application en therapeutique |
| FR2861071B1 (fr) | 2003-10-17 | 2006-01-06 | Sanofi Synthelabo | Derives de n-[phenyl(alkylpiperidin-2-yl) methyl]benzamide, leur prepartation et leur application en therapeutique |
| EP1702213A4 (en) * | 2003-12-09 | 2007-07-18 | Univ Leland Stanford Junior | METHOD AND COMPOSITIONS FOR MODULATING MITOCHONDRIAL ALDEHYDE DEHYDROGENASE-2 |
| US20080021083A1 (en) * | 2004-03-03 | 2008-01-24 | Daley Thomas E | 4-Methylpyrazole Formulations for Inhibiting Ethanol Intolerance |
| JP2007538024A (ja) * | 2004-05-19 | 2007-12-27 | 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 | アミロイドベータペプチドのレベル変化に関連する疾患及び状態の治療方法及び新規エノールカルボキサミド化合物 |
| CN1749415A (zh) * | 2004-09-15 | 2006-03-22 | 上海人类基因组研究中心 | 硝酸甘油治疗急性心绞痛疗效检测方法和试剂盒 |
| ATE538124T1 (de) | 2004-11-12 | 2012-01-15 | Bristol Myers Squibb Co | Imidazokondensierte tricyclische verbindungen auf thiazoloä4,5-büpyridin-basis und pharmazeutische zusammensetzungen damit |
| US7888374B2 (en) | 2005-01-28 | 2011-02-15 | Abbott Laboratories | Inhibitors of c-jun N-terminal kinases |
| DOP2006000051A (es) | 2005-02-24 | 2006-08-31 | Lilly Co Eli | Inhibidores de vegf-r2 y métodos |
| DE602006012713D1 (de) | 2005-09-23 | 2010-04-15 | Pfizer Prod Inc | Pyridinaminosulfonylsubstituierte benzamide als inhibitoren von cytochrom p450 3a4 (cyp3a4) |
| AU2006331765A1 (en) | 2005-12-22 | 2007-07-05 | Wyeth | Substituted isoquinoline-1,3(2H,4H)-diones, 1-thioxo-1,4-dihydro-2H-isoquinoline-3-ones and 1,4-dihydro-3(2H)-isoquinolones and use thereof as kinase inhibitor |
| JP2009531364A (ja) | 2006-03-28 | 2009-09-03 | ノバルティス アクチエンゲゼルシャフト | アミド誘導体およびｇタンパク質関連疾患の処置のためのそれらの使用 |
| JP5528699B2 (ja) | 2006-05-16 | 2014-06-25 | 武田薬品工業株式会社 | 縮合複素環化合物およびその用途 |
| US20080003585A1 (en) | 2006-06-29 | 2008-01-03 | Bio-Rad Laboratories, Inc., A Corporation Of The State Of Delaware | Purification and amplification of nucleic acids in a microfluidic device |
| EP2046769A2 (en) | 2006-07-27 | 2009-04-15 | Cv Therapeutics, Inc. | Aldh-2 inhibitors in the treatment of addiction |
| PE20080906A1 (es) | 2006-08-17 | 2008-07-05 | Kemia Inc | Derivados heteroarilo como inhibidores de citocina |
| WO2008024497A2 (en) | 2006-08-25 | 2008-02-28 | Vitae Pharmaceuticals, Inc. | INHIBITORS OF 11β -HYDROXYSTEROID DEHYDROGENASE TYPE 1 |
| ATE507205T1 (de) | 2006-12-11 | 2011-05-15 | Genetics Co Inc | Aromatische 1,4-di-carboxylamide und deren verwendung |
| JP5178738B2 (ja) | 2006-12-20 | 2013-04-10 | メルク・シャープ・アンド・ドーム・コーポレーション | 新規なｊｎｋ阻害剤 |
| WO2008103354A2 (en) | 2007-02-20 | 2008-08-28 | Cropsolution, Inc. | Modulators of acetyl-coenzyme a carboxylase and methods of use thereof |
| EP2131654A4 (en) * | 2007-03-02 | 2011-02-02 | Merck Sharp & Dohme | Bipyridine-carboxamide-orexin receptor Antagonist |
| CN101669030B (zh) | 2007-03-08 | 2016-01-13 | 小利兰·斯坦福大学托管委员会 | 线粒体醛脱氢酶2调节剂和其使用方法 |
| CA2709784A1 (en) | 2007-12-21 | 2009-07-09 | University Of Rochester | Method for altering the lifespan of eukaryotic organisms |
| RU2010153656A (ru) | 2008-06-04 | 2012-07-20 | Амбрилиа Байофарма Инк. (Ca) | Ингибиторы интегразы вич из пиридоксина |
| SG192439A1 (en) | 2008-06-27 | 2013-08-30 | Novartis Ag | Organic compounds |
| CN102209541B (zh) * | 2008-09-08 | 2016-05-18 | 小利兰·斯坦福大学托管委员会 | 醛脱氢酶活性调节剂和其使用方法 |
| WO2010062308A1 (en) | 2008-10-28 | 2010-06-03 | The Board Of Trustees Of The Leland Stanford Junior University | Modulators of aldehyde dehydrogenase and methods of use thereof |
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| US9102651B2 (en) | 2015-08-11 |
| CN101669030A (zh) | 2010-03-10 |
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| JP2015061836A (ja) | 2015-04-02 |
| WO2008112164A2 (en) | 2008-09-18 |
| CN101669030B (zh) | 2016-01-13 |
| US20120010248A1 (en) | 2012-01-12 |
| KR20090117950A (ko) | 2009-11-16 |
| EP2126574B1 (en) | 2015-12-23 |
| US9315484B2 (en) | 2016-04-19 |
| JP2010523476A (ja) | 2010-07-15 |
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| US20150105456A1 (en) | 2015-04-16 |
| US20110105602A2 (en) | 2011-05-05 |
| US20090082431A1 (en) | 2009-03-26 |
| EP2126574A4 (en) | 2012-02-22 |
| WO2008112164A3 (en) | 2008-11-13 |
| EP2126574A2 (en) | 2009-12-02 |
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