CN104151200B - Hdac抑制剂 - Google Patents

Hdac抑制剂 Download PDF

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Publication number
CN104151200B
CN104151200B CN201410312767.8A CN201410312767A CN104151200B CN 104151200 B CN104151200 B CN 104151200B CN 201410312767 A CN201410312767 A CN 201410312767A CN 104151200 B CN104151200 B CN 104151200B
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CN104151200A (zh
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A·H·戴维森
D·F·C·莫法特
F·A·戴
A·D·G·唐纳德
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GlaxoSmithKline Intellectual Property Development Ltd
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    • 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
    • C07C259/06—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 having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms
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    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
    • C07C311/19—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
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    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
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    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/34—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
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    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/56—Nitrogen atoms
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/56—Amides
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/20—Oxygen atoms
    • C07D215/22—Oxygen atoms attached in position 2 or 4
    • C—CHEMISTRY; METALLURGY
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    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/04—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
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    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
    • C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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    • C—CHEMISTRY; METALLURGY
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    • 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
    • C—CHEMISTRY; METALLURGY
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    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
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    • C07C2601/00—Systems containing only non-condensed rings
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    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
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    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

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CN201410312767.8A 2006-10-06 2007-09-14 Hdac抑制剂 Expired - Fee Related CN104151200B (zh)

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GBGB0619753.7A GB0619753D0 (en) 2006-10-06 2006-10-06 Enzyme inhibitors
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CN200780037335.9A CN101528677B (zh) 2006-10-06 2007-09-14 Hdac抑制剂

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CN104151200B true CN104151200B (zh) 2017-06-20

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US6777217B1 (en) 1996-03-26 2004-08-17 President And Fellows Of Harvard College Histone deacetylases, and uses related thereto
US20030129724A1 (en) 2000-03-03 2003-07-10 Grozinger Christina M. Class II human histone deacetylases, and uses related thereto
US7244853B2 (en) 2001-05-09 2007-07-17 President And Fellows Of Harvard College Dioxanes and uses thereof
CN101495116A (zh) 2005-03-22 2009-07-29 哈佛大学校长及研究员协会 蛋白降解病症的治疗
EP1964577B1 (en) * 2005-05-05 2016-04-13 GlaxoSmithKline Intellectual Property Development Limited Alpha aminoacid ester-drug conjugates hydrolysable by carboxylesterase
GB0509225D0 (en) * 2005-05-05 2005-06-15 Chroma Therapeutics Ltd Inhibitors of enzymatic activity
JP5441416B2 (ja) 2006-02-14 2014-03-12 プレジデント アンド フェロウズ オブ ハーバード カレッジ 二官能性ヒストンデアセチラーゼインヒビター
CN101484156B (zh) 2006-05-03 2015-11-25 哈佛大学校长及研究员协会 组蛋白脱乙酰基酶和微管蛋白脱乙酰基酶抑制剂
GB0619753D0 (en) 2006-10-06 2006-11-15 Chroma Therapeutics Ltd Enzyme inhibitors
JP5043120B2 (ja) * 2006-10-30 2012-10-10 クロマ セラピューティクス リミテッド ヒストンデアセチラーゼの阻害剤としてのヒドロキサメート
GB0803747D0 (en) 2008-02-29 2008-04-09 Martin Enzyme and receptor modulation
RU2515611C2 (ru) 2008-07-23 2014-05-20 Президент Энд Феллоуз Оф Гарвард Колледж Ингибиторы деацетилазы и их применение
DE102008062826A1 (de) 2008-12-23 2010-07-01 Merck Patent Gmbh Pyridazinonderivate
GB0903480D0 (en) * 2009-02-27 2009-04-08 Chroma Therapeutics Ltd Enzyme Inhibitors
US8716344B2 (en) 2009-08-11 2014-05-06 President And Fellows Of Harvard College Class- and isoform-specific HDAC inhibitors and uses thereof
US20110053925A1 (en) * 2009-08-28 2011-03-03 Novartis Ag Hydroxamate-Based Inhibitors of Deacetylases
WO2011113013A2 (en) 2010-03-11 2011-09-15 Hemaquest Pharmaceuticals, Inc. Methods and compositions for treating viral or virally-induced conditions
GB201009853D0 (en) 2010-06-11 2010-07-21 Chroma Therapeutics Ltd HSP90 inhibitors
WO2012025701A1 (en) 2010-08-25 2012-03-01 Chroma Therapeutics Ltd. Alpha, alpha - di substituted glycine ester derivatives and their use as hdac inhibitors
WO2012025155A1 (en) * 2010-08-26 2012-03-01 Novartis Ag Hydroxamate-based inhibitors of deacetylases
CN103189353A (zh) * 2010-08-27 2013-07-03 诺瓦提斯公司 基于异羟肟酸的脱乙酰酶抑制剂
CN101967113B (zh) * 2010-09-14 2012-08-22 北京欧凯纳斯科技有限公司 3-Alloc胺基-3-（3-硝基-4-氟苯基）丙酸及其制备方法
CN101985432B (zh) * 2010-09-15 2012-02-22 北京欧凯纳斯科技有限公司 3-Fmoc胺基-3-（3-硝基-4-氟苯基）丙酸及其制备方法
CN101962349B (zh) * 2010-09-15 2012-08-22 北京欧凯纳斯科技有限公司 3-Boc胺基-3-（3-硝基-4-氟苯基）丙酸及其制备方法
CN102532006A (zh) * 2012-01-31 2012-07-04 江西华士药业有限公司 治疗（类）风湿关节炎药物关键中间体6-甲基吡啶-3-甲醛的制备方法
WO2013142817A2 (en) 2012-03-23 2013-09-26 Dennis Brown Compositions and methods to improve the therapeutic benefit of indirubin and analogs thereof, including meisoindigo
US9387209B2 (en) 2012-04-10 2016-07-12 Annji Pharmaceutical Co., Ltd. Histone deacetylases (HDACs) inhibitors
WO2013169858A1 (en) 2012-05-08 2013-11-14 The Broad Institute, Inc. Diagnostic and treatment methods in patients having or at risk of developing resistance to cancer therapy
GB201211310D0 (en) 2012-06-26 2012-08-08 Chroma Therapeutics Ltd CSF-1R kinase inhibitors
MA37700B1 (fr) 2012-06-26 2018-03-30 Bayer Pharma AG N-[4-(quinolin-4-yloxy)cyclohexyl(méthyl)](hétéro)arylcarboxamides utilisables en tant qu'antagonistes des récepteurs aux androgènes, leur production et leur utilisation en tant que médicaments
DK3222616T3 (da) 2012-10-17 2019-08-19 Macrophage Pharma Ltd N-[2-{4-[6-amino-5-(2,4-difluorbenzoyl)-2-oxopyridin-1(2H)-yl]-3,5-difluorphenyl}ethyl]-L-alanin og terbutylester deraf
CN103172540B (zh) * 2013-03-18 2015-07-01 潍坊博创国际生物医药研究院 苯甘氨酸类组蛋白去乙酰酶抑制剂及其制备方法和应用
EA201792028A1 (ru) 2015-03-13 2018-04-30 Форма Терапьютикс, Инк. Альфа-цинамидные соединения и композиции как ингибиторы hdac8
CN105646297B (zh) * 2015-09-06 2017-12-29 杨东 一种生产贝利司他中间体的工艺方法
CN106496071B (zh) * 2015-09-07 2018-07-31 上海医药工业研究院 肉桂酰胺类化合物、其盐、中间体、制备方法及应用
CN108368035A (zh) 2015-12-18 2018-08-03 宝洁公司 在消费品中可用作感觉剂的环己烷酯衍生物的合成
WO2017216297A1 (en) 2016-06-16 2017-12-21 Glaxosmithkline Intellectual Property Development Limited Dosage regimen
CN109715173A (zh) 2016-07-15 2019-05-03 维拉克塔治疗公司 供基于nk细胞的疗法使用的hdac抑制剂
CN110621317B (zh) 2017-05-16 2023-05-12 安基生技新药股份有限公司 组蛋白去乙酰化酶（hdacs）抑制剂
GB201713975D0 (en) 2017-08-31 2017-10-18 Macrophage Pharma Ltd Medical use
US20210017174A1 (en) 2018-03-07 2021-01-21 Bayer Aktiengesellschaft Identification and use of erk5 inhibitor
CN212123220U (zh) * 2019-05-17 2020-12-11 依机国际有限公司 快速滑出式户外工具袋
EP3972963A1 (en) 2019-05-21 2022-03-30 Bayer Aktiengesellschaft Identification and use of kras inhibitors
PH12021552997A1 (en) 2019-05-31 2023-08-14 Viracta Subsidiary Inc Methods of treating virally associated cancers with histone deacetylase inhibitors
US20230212129A1 (en) 2020-06-08 2023-07-06 Annji Pharmaceutical Co., Ltd. Quinazoline derivatives useful as selective hdac6 inhibitors
KR20220134744A (ko) * 2021-03-26 2022-10-05 주식회사 종근당 다발성 경화증의 예방 또는 치료를 위한 조성물
CN113582911B (zh) * 2021-08-12 2024-03-12 山东大学 多靶点多奈哌齐-异羟肟酸型化合物及其制备方法和应用
KR20240086748A (ko) 2022-11-29 2024-06-19 숙명여자대학교산학협력단 Ent-7β-하이드록시-15-옥소카우르-16-엔-18-일 아세테이트를 유효성분으로 포함하는 골질환의 예방, 개선 또는 치료용 조성물

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1450991A (zh) * 2000-09-01 2003-10-22 诺瓦提斯公司 脱乙酰酶抑制剂
WO2004063169A1 (en) * 2003-01-13 2004-07-29 Astellas Pharma Inc. Hydroxamid acid derivatives as histone deacetylase (hdac) inhibitors
WO2006016680A1 (en) * 2004-08-09 2006-02-16 Astellas Pharma Inc. Hydroxyamide compounds having activity as inhibitors of histone deacetylase (hdac)

Family Cites Families (53)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1099355B (it) * 1978-10-12 1985-09-18 Sclavo Inst Sieroterapeut Composizione adatta alla determinazione in cinetica del glucosio
AU650953B2 (en) 1991-03-21 1994-07-07 Novartis Ag Inhaler
US5369108A (en) 1991-10-04 1994-11-29 Sloan-Kettering Institute For Cancer Research Potent inducers of terminal differentiation and methods of use thereof
US5783593A (en) 1993-11-04 1998-07-21 Abbott Laboratories Inhibitors of squalene synthetase and protein farnesyltransferase
TR200201052T2 (tr) 1999-09-08 2003-01-21 Sloan-Kettering Institute For Cancer Research Yeni hücre farklılaştırıcı ajanlar sınıfı ve hıstone deacetylase inhibitörleri, ve burada kullanım yöntemleri
DK1233958T3 (da) 1999-11-23 2011-10-17 Methylgene Inc Hæmmere af histondeacetylase
GB0003476D0 (en) 2000-02-16 2000-04-05 British Biotech Pharm Acetal Hydroxylamine compounds
WO2001070675A2 (en) 2000-03-24 2001-09-27 Methylgene, Inc. Inhibitors of histone deacetylase
EP2083005A1 (en) 2000-09-29 2009-07-29 TopoTarget UK Limited Carbamic acid compounds comprising an amide linkage as HDAC inhibitors
GB0023983D0 (en) 2000-09-29 2000-11-15 Prolifix Ltd Therapeutic compounds
EP2292593A3 (en) 2000-09-29 2011-05-25 TopoTarget UK Limited Carbamic acid compounds comprising a sulfonamide linkage as HDAC inhibitors
CA2434601A1 (en) 2001-01-12 2002-09-12 Methylgene, Inc. Methods for specifically inhibiting histone deacetylase-4
US6784173B2 (en) 2001-06-15 2004-08-31 Hoffmann-La Roche Inc. Aromatic dicarboxylic acid derivatives
US20040091951A1 (en) 2002-02-07 2004-05-13 Axys Pharmaceuticals, Inc. Assay for measuring acetylation or deacetylation activity of an enzyme
KR20040094672A (ko) 2002-03-13 2004-11-10 얀센 파마슈티카 엔.브이. 히스톤 디아세틸라제의 신규한 저해제로서의설포닐아미노-유도체
EP1485348B1 (en) 2002-03-13 2008-06-11 Janssen Pharmaceutica N.V. Carbonylamino-derivatives as novel inhibitors of histone deacetylase
AU2003218738B2 (en) 2002-03-13 2009-01-08 Janssen Pharmaceutica N.V. Sulfonyl-derivatives as novel inhibitors of histone deacetylase
ES2347544T3 (es) 2002-03-13 2010-11-02 Janssen Pharmaceutica Nv Inhibidores de histona-desacetilasas.
JP4606027B2 (ja) 2002-04-03 2011-01-05 トポターゲット ユーケー リミテッド Ｈｄａｃ阻害剤としてのピペラジン結合を有するカルバミン酸化合物
TWI319387B (en) 2002-04-05 2010-01-11 Astrazeneca Ab Benzamide derivatives
GB0209715D0 (en) 2002-04-27 2002-06-05 Astrazeneca Ab Chemical compounds
JP2005539001A (ja) 2002-08-02 2005-12-22 アージェンタ・ディスカバリー・リミテッド ヒストンデアセチラーゼインヒビターとしての置換チエニルヒドロキサム酸
US20060032823A1 (en) 2002-09-04 2006-02-16 Harrison Alan D Disinfection of reverse osmosis membrane
US7221775B2 (en) 2002-11-12 2007-05-22 Intellivid Corporation Method and apparatus for computerized image background analysis
AU2004215624B2 (en) 2003-02-25 2011-06-02 Topotarget Uk Limited Hydroxamic acid compounds comprising a bicyclic heteroaryl group as HDAC inhibitors
ES2328819T3 (es) 2003-04-07 2009-11-18 Pharmacyclics, Inc. Hidroxamatos como agentes terapeuticos.
WO2004110989A1 (en) 2003-05-14 2004-12-23 Bayer Pharmaceuticals Corporation N-hydroxy-7-(arylamino)heptanamide derivatives useful for treating hyper-proliferative disorders
CA2531661C (en) 2003-07-07 2013-03-12 Georgetown University Histone deacetylase inhibitors and methods of use thereof
WO2005004861A1 (en) 2003-07-15 2005-01-20 Korea Research Institute Of Bioscience And Biotechnology A use of novel 2-oxo-heterocyclic compounds and the pharmaceutical compositions comprising the same
WO2005014588A1 (en) 2003-08-01 2005-02-17 Argenta Discovery Limited Substituted thienyl-hydroxamic acids having histone deacetylase activity
JP2007501775A (ja) 2003-08-07 2007-02-01 ノバルティス アクチエンゲゼルシャフト 免疫抑制剤としてのヒストンデアセチラーゼ阻害剤
MXPA05011286A (es) 2003-08-20 2006-01-24 Axys Pharm Inc Derivados de acetileno como inhibidores de histona deacetilasa.
PL379887A1 (pl) 2003-08-26 2006-11-27 Merck Hdac Research, Llc Sposób leczenia raka inhibitorami HDAC
AR046411A1 (es) 2003-09-22 2005-12-07 S Bio Pte Ltd Derivados de bencimidazol. aplicaciones farmaceuticas
CA2539117A1 (en) 2003-09-24 2005-04-07 Methylgene Inc. Inhibitors of histone deacetylase
CZ2004770A3 (cs) 2004-06-29 2006-02-15 Pavelka@Miloslav Zpusob detekce únavy operátora ze svalové cinnosti a zarízení k provádení tohoto zpusobu
GB0509223D0 (en) * 2005-05-05 2005-06-15 Chroma Therapeutics Ltd Enzyme inhibitors
GB0509227D0 (en) * 2005-05-05 2005-06-15 Chroma Therapeutics Ltd Intracellular enzyme inhibitors
EP1964577B1 (en) * 2005-05-05 2016-04-13 GlaxoSmithKline Intellectual Property Development Limited Alpha aminoacid ester-drug conjugates hydrolysable by carboxylesterase
GB0509225D0 (en) * 2005-05-05 2005-06-15 Chroma Therapeutics Ltd Inhibitors of enzymatic activity
GB0510204D0 (en) * 2005-05-19 2005-06-22 Chroma Therapeutics Ltd Enzyme inhibitors
CA2608929C (en) * 2005-06-23 2014-01-28 Janssen Pharmaceutica N.V. Imidazolinone and hydantoine derivatives as novel inhibitors of histone deacetylase
AU2007246869B2 (en) * 2006-05-04 2012-10-18 Macrophage Pharma Limited p38 MAP kinase inhibitors
GB0608823D0 (en) * 2006-05-04 2006-06-14 Chroma Therapeutics Ltd Inhibitors of P13 kinase
GB0608837D0 (en) * 2006-05-04 2006-06-14 Chroma Therapeutics Ltd Inhibitors of MAP kinase
GB0608821D0 (en) * 2006-05-04 2006-06-14 Chroma Therapeutics Ltd DHFR enzyme inhibitors
GB0619753D0 (en) 2006-10-06 2006-11-15 Chroma Therapeutics Ltd Enzyme inhibitors
AU2007310604B2 (en) * 2006-10-25 2012-02-02 Chroma Therapeutics Ltd. Pteridine derivatives as polo-like kinase inhibitors useful in the treatment of cancer
GB0621203D0 (en) * 2006-10-25 2006-12-06 Chroma Therapeutics Ltd PLK inhibitors
JP5043120B2 (ja) * 2006-10-30 2012-10-10 クロマ セラピューティクス リミテッド ヒストンデアセチラーゼの阻害剤としてのヒドロキサメート
ATE522516T1 (de) * 2006-11-01 2011-09-15 Chroma Therapeutics Ltd Inhibitoren der ikk-beta-serin-threonin- proteinkinase
WO2008053185A1 (en) * 2006-11-01 2008-05-08 Chroma Therapeutics Ltd. INHIBITORS OF IKK-β SERINE-THREONINE PROTEIN KINASE
GB0622084D0 (en) * 2006-11-06 2006-12-13 Chroma Therapeutics Ltd Inhibitors of HSP90

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1450991A (zh) * 2000-09-01 2003-10-22 诺瓦提斯公司 脱乙酰酶抑制剂
WO2004063169A1 (en) * 2003-01-13 2004-07-29 Astellas Pharma Inc. Hydroxamid acid derivatives as histone deacetylase (hdac) inhibitors
WO2006016680A1 (en) * 2004-08-09 2006-02-16 Astellas Pharma Inc. Hydroxyamide compounds having activity as inhibitors of histone deacetylase (hdac)

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