HK1142597A1 - 組蛋白脫乙酰酶抑制劑 - Google Patents

組蛋白脫乙酰酶抑制劑

Info

Publication number
HK1142597A1
HK1142597A1 HK10109070.2A HK10109070A HK1142597A1 HK 1142597 A1 HK1142597 A1 HK 1142597A1 HK 10109070 A HK10109070 A HK 10109070A HK 1142597 A1 HK1142597 A1 HK 1142597A1
Authority
HK
Hong Kong
Prior art keywords
inhibitors
histone deacetylase
deacetylase
histone
Prior art date
Application number
HK10109070.2A
Other languages
English (en)
Inventor
Sylvie Frechette
Lubo Isakovic
Isabelle Paquin
Simon Roy
Oscar Moradei
Arkadii Vaisburg
Original Assignee
梅特希爾基因公司
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 梅特希爾基因公司 filed Critical 梅特希爾基因公司
Publication of HK1142597A1 publication Critical patent/HK1142597A1/zh

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02Heterocyclic 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
    • C07D403/12Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic 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
    • C07D401/02Heterocyclic 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
    • C07D401/12Heterocyclic 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D207/00Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
    • C07D207/10Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
    • C07D207/14Nitrogen atoms not forming part of a nitro radical
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic 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
    • C07D401/02Heterocyclic 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
    • C07D401/04Heterocyclic 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 directly linked by a ring-member-to-ring-member bond
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02Heterocyclic 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
    • C07D403/04Heterocyclic 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 directly linked by a ring-member-to-ring-member bond
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic 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
    • C07D405/02Heterocyclic 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
    • C07D405/12Heterocyclic 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Epidemiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyrrole Compounds (AREA)
HK10109070.2A 2007-03-13 2010-09-22 組蛋白脫乙酰酶抑制劑 HK1142597A1 (zh)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US90673307P 2007-03-13 2007-03-13
US12/043,450 US8030344B2 (en) 2007-03-13 2008-03-06 Inhibitors of histone deacetylase
PCT/CA2008/000455 WO2008109994A1 (en) 2007-03-13 2008-03-12 Inhibitors of histone deacetylase

Publications (1)

Publication Number Publication Date
HK1142597A1 true HK1142597A1 (zh) 2010-12-10

Family

ID=39758948

Family Applications (1)

Application Number Title Priority Date Filing Date
HK10109070.2A HK1142597A1 (zh) 2007-03-13 2010-09-22 組蛋白脫乙酰酶抑制劑

Country Status (10)

Country Link
US (2) US8030344B2 (zh)
EP (1) EP2134680B1 (zh)
JP (2) JP2010520893A (zh)
KR (2) KR101678611B1 (zh)
CN (1) CN101679239B (zh)
CA (1) CA2680467C (zh)
ES (1) ES2565243T3 (zh)
HK (1) HK1142597A1 (zh)
TW (1) TWI549676B (zh)
WO (1) WO2008109994A1 (zh)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8030344B2 (en) * 2007-03-13 2011-10-04 Methylgene Inc. Inhibitors of histone deacetylase
EP2217588A4 (en) * 2007-11-02 2013-12-04 Methylgene Inc INHIBITORS OF HISTONE DEACETYLASE
EP2330894B8 (en) 2008-09-03 2017-04-19 BioMarin Pharmaceutical Inc. Compositions including 6-aminohexanoic acid derivatives as hdac inhibitors
CN102300845A (zh) * 2009-02-23 2011-12-28 霍夫曼-拉罗奇有限公司 用于治疗癌症的新型邻氨基酰胺类
JP2013509441A (ja) 2009-10-30 2013-03-14 マサチューセッツ インスティテュート オブ テクノロジー 記憶/認知および不安障害の処置のためのci−994およびジナリンの使用
WO2012068589A2 (en) * 2010-11-19 2012-05-24 Constellation Pharmaceuticals Modulators of methyl modifying enzymes, compositions and uses thereof
US8957066B2 (en) 2011-02-28 2015-02-17 Biomarin Pharmaceutical Inc. Histone deacetylase inhibitors
US10059723B2 (en) 2011-02-28 2018-08-28 Biomarin Pharmaceutical Inc. Histone deacetylase inhibitors
DK2680694T3 (en) 2011-02-28 2019-03-25 Biomarin Pharm Inc HISTONDEACETYLASE INHIBITORS
CN102775368B (zh) * 2011-05-10 2016-08-17 上海驺虞医药科技有限公司 一类噻唑类化合物及其制备方法和用途
US9206128B2 (en) 2011-11-18 2015-12-08 Constellation Pharmaceuticals, Inc. Modulators of methyl modifying enzymes, compositions and uses thereof
EP2780013A4 (en) 2011-11-18 2015-07-01 Constellation Pharmaceuticals Inc MODULATORS OF METHYL MODIFYING ENZYMES, COMPOSITIONS AND USES THEREOF
US9085583B2 (en) 2012-02-10 2015-07-21 Constellation—Pharmaceuticals, Inc. Modulators of methyl modifying enzymes, compositions and uses thereof
AU2014228344C1 (en) 2013-03-15 2019-02-07 Biomarin Pharmaceutical Inc. HDAC inhibitors
WO2014151142A1 (en) 2013-03-15 2014-09-25 Constellation Pharmaceuticals, Inc. Modulators of methyl modifying enzymes, compositions and uses thereof
US9969716B2 (en) 2013-08-15 2018-05-15 Constellation Pharmaceuticals, Inc. Indole derivatives as modulators of methyl modifying enzymes, compositions and uses thereof
US9274117B2 (en) * 2013-12-21 2016-03-01 Catholic University Industry Academic Use of SIRT7 as novel cancer therapy target and method for treating cancer using the same
US9636298B2 (en) 2014-01-17 2017-05-02 Methylgene Inc. Prodrugs of compounds that enhance antifungal activity and compositions of said prodrugs
GB201501870D0 (en) * 2015-02-04 2015-03-18 Cancer Rec Tech Ltd Autotaxin inhibitors
JP2018525342A (ja) * 2015-07-02 2018-09-06 バイオマリン ファーマシューティカル インコーポレイテッド ヒストンデアセチラーゼ阻害剤
WO2017040190A1 (en) 2015-08-28 2017-03-09 Constellation Pharmaceuticals, Inc. Crystalline forms of (r)-n-((4-methoxy-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-2-methyl-1-(1-(1-(2,2,2-trifluoroethyl)piperidin-4-yl)ethyl)-1h-indole-3-carboxamide
WO2018075598A1 (en) 2016-10-19 2018-04-26 Constellation Pharmaceuticals, Inc. Synthesis of inhibitors of ezh2

Family Cites Families (55)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2754286A (en) 1951-10-15 1956-07-10 Du Pont Aldehydes and their acetals
CH431764A (de) 1959-05-06 1967-03-15 Sandoz Ag Verfahren zur Herstellung metallhaltiger Reaktivfarbstoffe
US3263924A (en) 1963-09-13 1966-08-02 Dole Valve Co Heating and cooling zone valve
WO1986005779A1 (en) 1985-04-03 1986-10-09 Yamanouchi Pharmaceutical Co., Ltd. Phenylene derivatives
US5149797A (en) 1990-02-15 1992-09-22 The Worcester Foundation For Experimental Biology Method of site-specific alteration of rna and production of encoded polypeptides
US5332750A (en) 1991-09-04 1994-07-26 Merck Patent Gesellschaft Mit Beschrankter Haftung 1,2-dihydro-2-oxopyridines
US5652355A (en) 1992-07-23 1997-07-29 Worcester Foundation For Experimental Biology Hybrid oligonucleotide phosphorothioates
DE19510957A1 (de) 1995-03-25 1996-09-26 Huels Chemische Werke Ag Eingedickter Bodenverfestiger, sowie diesen enthaltende verpackte Fertigmischung für Bodenbehandlungen
JP4105451B2 (ja) 1996-09-30 2008-06-25 バイエル・シエーリング・ファーマ アクチエンゲゼルシャフト 分化誘導剤
US6174905B1 (en) 1996-09-30 2001-01-16 Mitsui Chemicals, Inc. Cell differentiation inducer
US6794392B1 (en) 1996-09-30 2004-09-21 Schering Aktiengesellschaft Cell differentiation inducer
US6034251A (en) 1997-11-07 2000-03-07 Schering Corporation Phenyl-alkyl-imidazoles
US5905084A (en) * 1997-11-14 1999-05-18 Eli Lilly And Company 5-HTIF -agonists effective in treating migraine
JPH11318492A (ja) 1998-03-09 1999-11-24 Aisin Seiki Co Ltd 蛍光発生性基質を含有する組成物
JPH11269146A (ja) 1998-03-24 1999-10-05 Mitsui Chem Inc 分化誘導剤
JP4405602B2 (ja) 1998-04-16 2010-01-27 バイエル・シエーリング・ファーマ アクチエンゲゼルシャフト ヒストン脱アセチル化酵素阻害剤
JP2000256194A (ja) 1999-01-06 2000-09-19 Mitsui Chemicals Inc 核内レセプタ作動薬およびその効果増強剤
US6653309B1 (en) 1999-04-26 2003-11-25 Vertex Pharmaceuticals Incorporated Inhibitors of IMPDH enzyme technical field of the invention
CA2366408A1 (en) 1999-05-03 2000-11-30 Methylgene, Inc. Inhibition of histone deacetylase
JP4360660B2 (ja) 1999-11-09 2009-11-11 三井化学株式会社 モノアシルフェニレンジアミン誘導体の精製法
US6541661B1 (en) 1999-11-23 2003-04-01 Methylgene, Inc. Inhibitors of histone deacetylase
AU2001241128A1 (en) 2000-03-14 2001-09-24 Fujisawa Pharmaceutical Co. Ltd. Novel amide compounds
CA2404002A1 (en) 2000-03-24 2001-09-27 Methylgene, Inc. Inhibitors of histone deacetylase
KR20040018328A (ko) 2001-01-12 2004-03-03 메틸진, 인크. 히스톤 디아세틸라제-4를 특이적으로 억제하는 방법
US6897220B2 (en) 2001-09-14 2005-05-24 Methylgene, Inc. Inhibitors of histone deacetylase
AU2002327627B2 (en) 2001-09-14 2006-09-14 Methylgene Inc. Inhibitors of histone deacetylase
US7868204B2 (en) 2001-09-14 2011-01-11 Methylgene Inc. Inhibitors of histone deacetylase
US20060058553A1 (en) * 2002-02-07 2006-03-16 Axys Pharmaceuticals, Inc. Novel bicyclic hydroxamates as inhibitors of histone deacetylase
CN100445276C (zh) 2002-03-13 2008-12-24 詹森药业有限公司 用作组蛋白去乙酰酶抑制剂的磺酰基衍生物
EA007272B1 (ru) 2002-03-13 2006-08-25 Янссен Фармацевтика Н. В. Новые ингибиторы гистондеацетилазы
US7767679B2 (en) 2002-03-13 2010-08-03 Janssen Pharmaceutica N.V. Sulfonylamino-derivatives as novel inhibitors of histone deacetylase
EP1485348B1 (en) 2002-03-13 2008-06-11 Janssen Pharmaceutica N.V. Carbonylamino-derivatives as novel inhibitors of histone deacetylase
WO2003076438A1 (en) 2002-03-13 2003-09-18 Janssen Pharmaceutica N.V. Piperazinyl-, piperidinyl- and morpholinyl-derivatives as novel inhibitors of histone deacetylase
CN100451001C (zh) 2002-03-14 2009-01-14 日本曹达株式会社 酚性化合物及使用酚性化合物的记录材料
TWI319387B (en) 2002-04-05 2010-01-11 Astrazeneca Ab Benzamide derivatives
GB0209715D0 (en) * 2002-04-27 2002-06-05 Astrazeneca Ab Chemical compounds
US20040072770A1 (en) 2002-07-03 2004-04-15 Besterman Jeffrey M. Methods for specifically inhibiting histone deacetylase-7 and 8
US7282608B2 (en) 2002-10-17 2007-10-16 Methylgene, Inc. Inhibitors of histone deacetylase
US7135575B2 (en) * 2003-03-03 2006-11-14 Array Biopharma, Inc. P38 inhibitors and methods of use thereof
AR043633A1 (es) 2003-03-20 2005-08-03 Schering Corp Ligandos de receptores de canabinoides
WO2005030705A1 (en) 2003-09-24 2005-04-07 Methylgene, Inc. Inhibitors of histone deacetylase
CA2559733C (en) 2004-03-26 2014-05-13 Methylgene Inc. Inhibitors of histone deacetylase
US7253204B2 (en) 2004-03-26 2007-08-07 Methylgene Inc. Inhibitors of histone deacetylase
CA2581356A1 (en) 2004-09-22 2006-03-22 Methylgene Inc. Histone deacetylase whole cell enzyme assay
US7642275B2 (en) * 2004-12-16 2010-01-05 Takeda San Diego, Inc. Histone deacetylase inhibitors
JP4853824B2 (ja) * 2005-01-20 2012-01-11 アステラス製薬株式会社 キノロン誘導体を有効成分とする医薬組成物
WO2006115845A1 (en) * 2005-04-20 2006-11-02 Merck & Co., Inc. Benzothiophene derivatives
EP1896436A2 (en) 2005-05-11 2008-03-12 Takeda San Diego, Inc. Histone deacetylase inhibitors
WO2006122926A1 (en) * 2005-05-18 2006-11-23 Janssen Pharmaceutica N.V. Substituted aminopropenyl piperidine or morpholine derivatives as novel inhibitors of histone deacetylase
CN101263121A (zh) 2005-07-14 2008-09-10 塔克达圣地亚哥公司 组蛋白脱乙酰基酶抑制剂
JP2009514859A (ja) * 2005-11-03 2009-04-09 メルク エンド カムパニー インコーポレーテッド 置換ニコチンアミド化合物
AR057579A1 (es) * 2005-11-23 2007-12-05 Merck & Co Inc Compuestos espirociclicos como inhibidores de histona de acetilasa (hdac)
EP1976835A2 (en) 2006-01-13 2008-10-08 Takeda San Diego, Inc. Histone deacetylase inhibitors
US8598168B2 (en) 2006-04-07 2013-12-03 Methylgene Inc. Inhibitors of histone deacetylase
US8030344B2 (en) * 2007-03-13 2011-10-04 Methylgene Inc. Inhibitors of histone deacetylase

Also Published As

Publication number Publication date
EP2134680A1 (en) 2009-12-23
US8030344B2 (en) 2011-10-04
WO2008109994A1 (en) 2008-09-18
US8354445B2 (en) 2013-01-15
ES2565243T3 (es) 2016-04-01
JP2010520893A (ja) 2010-06-17
JP5885311B2 (ja) 2016-03-15
KR101678611B1 (ko) 2016-11-22
CA2680467C (en) 2016-11-08
JP2014159417A (ja) 2014-09-04
TWI549676B (zh) 2016-09-21
TW200848015A (en) 2008-12-16
CA2680467A1 (en) 2008-09-18
CN101679239A (zh) 2010-03-24
EP2134680B1 (en) 2016-01-13
CN101679239B (zh) 2014-12-10
KR20090119004A (ko) 2009-11-18
KR20150080025A (ko) 2015-07-08
US20080227826A1 (en) 2008-09-18
US20110212965A1 (en) 2011-09-01
EP2134680A4 (en) 2012-03-07

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PC Patent ceased (i.e. patent has lapsed due to the failure to pay the renewal fee)

Effective date: 20210315