CA2700173C - Methods of synthesis of certain hydroxamic acid compounds - Google Patents

Methods of synthesis of certain hydroxamic acid compounds Download PDF

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Publication number
CA2700173C
CA2700173C CA2700173A CA2700173A CA2700173C CA 2700173 C CA2700173 C CA 2700173C CA 2700173 A CA2700173 A CA 2700173A CA 2700173 A CA2700173 A CA 2700173A CA 2700173 C CA2700173 C CA 2700173C
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Prior art keywords
compound
formula
independently
reacting
carboxylic acid
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CA2700173A
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English (en)
French (fr)
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CA2700173A1 (en
Inventor
Helge A. Reisch
Peter Leeming
Prasad S. Raje
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Topotarget UK Ltd
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Topotarget UK Ltd
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/36Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
    • C07C303/40Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reactions not involving the formation of sulfonamide groups
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • A61P17/06Antipsoriatics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00Antiparasitic agents
    • A61P33/02Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
    • A61P33/06Antimalarials
    • 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

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Dermatology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
CA2700173A 2007-09-25 2008-09-23 Methods of synthesis of certain hydroxamic acid compounds Active CA2700173C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US97488007P 2007-09-25 2007-09-25
US60/974,880 2007-09-25
PCT/GB2008/003226 WO2009040517A2 (en) 2007-09-25 2008-09-23 Methods of synthesis of certain hydroxamic acid compounds

Publications (2)

Publication Number Publication Date
CA2700173A1 CA2700173A1 (en) 2009-04-02
CA2700173C true CA2700173C (en) 2016-10-11

Family

ID=40293778

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2700173A Active CA2700173C (en) 2007-09-25 2008-09-23 Methods of synthesis of certain hydroxamic acid compounds

Country Status (7)

Country Link
US (1) US8642809B2 (https=)
EP (1) EP2203421B1 (https=)
JP (1) JP2010540426A (https=)
CN (1) CN101868446A (https=)
CA (1) CA2700173C (https=)
MX (1) MX2010003230A (https=)
WO (1) WO2009040517A2 (https=)

Families Citing this family (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9962368B2 (en) 2009-01-09 2018-05-08 Board Of Regents Of The University Of Texas System Pro-neurogenic compounds
US8362277B2 (en) 2009-01-09 2013-01-29 Board Of Regents Of The University Of Texas System Pro-neurogenic compounds
US9162980B2 (en) 2009-01-09 2015-10-20 Board Of Regents Of The University Of Texas System Anti-depression compounds
EP2385829B1 (en) 2009-01-09 2018-08-01 Board of Regents of the University of Texas System Pro-neurogenic compounds
US9095572B2 (en) 2009-01-09 2015-08-04 Board Of Regents Of The University Of Texas System Pro-neurogenic compounds
EP2451790A4 (en) * 2009-07-07 2012-12-26 Anthem Biosciences Private Ltd INHIBITORS OF HISTONE DEACETYLASE
CN102531972A (zh) * 2010-12-31 2012-07-04 北京万全阳光医药科技有限公司 抗肿瘤药物Belinostat的中间体的制备方法
CN102786448B (zh) * 2012-08-09 2014-03-12 深圳万乐药业有限公司 一种合成belinostat的方法
AU2013305591B2 (en) 2012-08-24 2017-04-13 Board Of Regents Of The University Of Texas System Pro-neurogenic compounds
WO2015070237A1 (en) 2013-11-11 2015-05-14 Board Of Regents Of The University Of Texas System Neuroprotective chemicals and methods for identifying and using same
WO2015070234A2 (en) 2013-11-11 2015-05-14 Board Of Regents Of The University Of Texas System Neuroprotective compounds and use thereof
CN103724239A (zh) * 2013-12-31 2014-04-16 无锡万全医药技术有限公司 一种3-(3-苯基氨磺酰基-苯基)-丙烯酸酯的制备方法
CN103787924A (zh) * 2014-01-14 2014-05-14 北京万全德众医药生物技术有限公司 抗肿瘤药物Belinostat的一种新纯化方法
CN104478769B (zh) * 2014-12-22 2016-01-06 深圳万乐药业有限公司 一种适合工业化生产的贝利司他合成方法
CN105367455B (zh) * 2015-12-18 2017-10-24 深圳万乐药业有限公司 一种贝利司他异构体的制备方法
CN109462980B (zh) 2016-03-15 2022-02-08 奥莱松基因组股份有限公司 用于治疗血液恶性肿瘤的lsd1抑制剂的组合
ES3057783T3 (en) 2016-03-15 2026-03-04 Oryzon Genomics Sa Combinations of lsd1 inhibitors for use in the treatment of neoplastic diseases
US20190256459A1 (en) * 2016-05-17 2019-08-22 Biophore India Pharmaceuticals Pvt. Ltd. Novel process for the preparation of belinostat
ES2879294T3 (es) * 2016-07-26 2021-11-22 Fresenius Kabi Oncology Ltd Formas polimórficas de Belinostat y procesos para la preparación de las mismas
WO2018029699A1 (en) * 2016-08-11 2018-02-15 Msn Research & Development Center Solid state forms of (2e)-n-hydroxy-3-[3-(phenylsulfamoyl)phenyl]prop-2-enamide and process for preparation thereof
CN106565552A (zh) * 2016-10-31 2017-04-19 瑞阳制药有限公司 贝利司他结晶体及其制备方法
RU2748835C1 (ru) 2017-11-27 2021-05-31 Совет Научных И Прикладных Исследований Индол(сульфонил)-n-гидроксибензамидные производные в качестве селективных ингибиторов hdac
CN108033902B (zh) * 2017-12-26 2020-07-07 深圳万乐药业有限公司 一种高纯度贝利司他顺式异构体的制备方法
CN109265377B (zh) * 2018-10-25 2021-01-22 瑞阳制药股份有限公司 贝利司他的绿色合成方法
CN109336788A (zh) * 2018-10-31 2019-02-15 安徽省庆云医药股份有限公司 一种贝利司他的制备方法
CN111848591B (zh) * 2019-04-25 2022-03-18 成都先导药物开发股份有限公司 Hdac抑制剂及其制备方法和用途
CN115636774B (zh) * 2022-12-01 2023-12-22 南开大学 一种贝利司他的合成方法
CN119456224B (zh) * 2024-10-31 2025-11-28 郑州大学 一种矿物的预处理方法协同浮选药剂的分离工艺

Family Cites Families (92)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4642316A (en) * 1985-05-20 1987-02-10 Warner-Lambert Company Parenteral phenytoin preparations
US6071923A (en) * 1994-09-16 2000-06-06 Bar-Ilan University Retinoyloxy aryl-substituted alkylene butyrates useful for the treatment of cancer and other proliferative diseases
US5730977A (en) 1995-08-21 1998-03-24 Mitsui Toatsu Chemicals, Inc. Anti-VEGF human monoclonal antibody
EP0827742A1 (en) 1996-09-04 1998-03-11 Vrije Universiteit Brussel Use of histone deacetylase inhibitors for treating fribosis or cirrhosis
BR9914779A (pt) * 1998-10-13 2001-07-03 Fujisawa Pharmaceutical Co Composto wf27082, processo para sua produção, composição farmacêutica contendo o mesmo, cepa de fundos pertencente ao gênero acremonium, composto tendo atividade inibidora de desacetilase de histona, processo para sua produção, seu método e uso
US20070148228A1 (en) * 1999-02-22 2007-06-28 Merrion Research I Limited Solid oral dosage form containing an enhancer
EP1179541B1 (en) * 1999-04-28 2004-06-16 Board Of Regents, The University Of Texas System Compositions and methods for cancer treatment by selectively inhibiting VEGF
KR20020070285A (ko) * 1999-11-23 2002-09-05 메틸진, 인크. 히스톤 디아세틸라제의 억제제
EP1335898B1 (en) 2000-09-29 2005-11-23 TopoTarget UK Limited Carbamic acid compounds comprising an amide linkage as hdac inhibitors
CA2423744C (en) * 2000-09-29 2012-04-03 Prolifix Limited Hydroxamic acid compounds comprising a sulfonamide linkage as hdac inhibitors
GB0023983D0 (en) * 2000-09-29 2000-11-15 Prolifix Ltd Therapeutic compounds
JPWO2002074298A1 (ja) * 2001-03-21 2004-07-08 小野薬品工業株式会社 Il−6産生阻害剤
ES2310213T3 (es) 2001-05-02 2009-01-01 The Regents Of The University Of California Procedimiento para tratar trastornos neurodegenerativos, psiquiatricos y otros trastornos con inhibidores de desacetilasa.
MXPA04001253A (es) * 2001-08-09 2004-06-03 Ono Pharmaceutical Co Derivados de acidos carboxilicos y agente farmaceutico que comprende los mismos como ingrediente activo.
HU229521B1 (hu) 2001-08-21 2014-01-28 Astellas Pharma Inc A hiszton-dezacetiláz inhibitor gyógyászati alkalmazása, és eljárás tumorellenes hatásának kiértékelésére
US6897220B2 (en) * 2001-09-14 2005-05-24 Methylgene, Inc. Inhibitors of histone deacetylase
EP1293205A1 (en) 2001-09-18 2003-03-19 G2M Cancer Drugs AG Valproic acid and derivatives thereof for the combination therapy of human cancers, for the treatment of tumour metastasis and minimal residual disease
NZ533737A (en) * 2002-01-11 2006-02-24 Matthias Rath A nutrient pharmaceutical formulation comprising polyphenols and use in treatment of cancer
JP2005517007A (ja) 2002-02-07 2005-06-09 アクシス・ファーマスーティカルズ ヒストンデアセチラーゼ阻害剤としての新規二環式ヒドロキサメート
JP2005525345A (ja) * 2002-02-15 2005-08-25 スローン−ケッタリング・インスティテュート・フォー・キャンサー・リサーチ Trx媒介性疾患を処置する方法
US20050288227A1 (en) * 2002-02-15 2005-12-29 Marks Paul A Use of thioredoxin measurements for diagnostics and treatments
US20070060614A1 (en) * 2002-03-04 2007-03-15 Bacopoulos Nicholas G Methods of treating cancer with hdac inhibitors
US7148257B2 (en) * 2002-03-04 2006-12-12 Merck Hdac Research, Llc Methods of treating mesothelioma with suberoylanilide hydroxamic acid
US20040132825A1 (en) * 2002-03-04 2004-07-08 Bacopoulos Nicholas G. Methods of treating cancer with HDAC inhibitors
WO2003075839A2 (en) * 2002-03-04 2003-09-18 Aton Pharma, Inc. Methods of inducing terminal differentiation
DE60326436D1 (en) 2002-03-13 2009-04-16 Janssen Pharmaceutica Nv Aminoderivate als histone-deacetylase-inhibitoren
CA2479906C (en) 2002-04-03 2011-02-08 Topotarget Uk Limited Carbamic acid compounds comprising a piperazine linkage as hdac inhibitors
TWI319387B (en) 2002-04-05 2010-01-11 Astrazeneca Ab Benzamide derivatives
WO2003087066A1 (en) * 2002-04-11 2003-10-23 Sk Chemicals, Co., Ltd. α,β-UNSATURATED HYDROXAMIC ACID DERIVATIVES AND THEIR USE AS HISTONE DEACETYLASE INHIBITORS
CN100566711C (zh) * 2002-04-15 2009-12-09 斯隆-凯特林癌症研究院 治疗癌症的化合物及其用途
US8883148B2 (en) * 2002-04-26 2014-11-11 Asan Laboratories Company (Cayman), Limited Prevention of joint destruction
GB0209715D0 (en) 2002-04-27 2002-06-05 Astrazeneca Ab Chemical compounds
DE10233412A1 (de) 2002-07-23 2004-02-12 4Sc Ag Neue Verbindungen als Histondeacetylase-Inhibitoren
PL374970A1 (en) 2002-08-02 2005-11-14 Argenta Discovery Limited Substituted thienyl-hydroxamic acids as histone deacetylase inhibitors
US20080004311A1 (en) * 2002-11-12 2008-01-03 Alcon, Inc. Histone deacetylase inhibitors for treating degenerative diseases of the eye
GB0226370D0 (en) 2002-11-12 2002-12-18 Novartis Ag Organic compounds
ITMI20030025A1 (it) 2003-01-10 2004-07-11 Italfarmaco Spa Derivati dell'acido idrossammico ad attivita' antinfiammatoria.
TW200418806A (en) 2003-01-13 2004-10-01 Fujisawa Pharmaceutical Co HDAC inhibitor
US20050222013A1 (en) * 2003-01-16 2005-10-06 Georgetown University Methods for the use of inhibitors of histone deacetylase as synergistic agents in cancer therapy
TW200424174A (en) 2003-02-06 2004-11-16 Hoffmann La Roche New TP diamide
AU2003900608A0 (en) 2003-02-11 2003-02-27 Fujisawa Pharmaceutical Co., Ltd. Hdac inhibitor
US7244751B2 (en) 2003-02-14 2007-07-17 Shenzhen Chipscreen Biosciences Ltd. Histone deacetylase inhibitors of novel benzamide derivatives with potent differentiation and anti-proliferation activity
JP2006518219A (ja) 2003-02-18 2006-08-10 マックスサイト インコーポレーティッド 電気穿孔法による細胞への抗原の負荷方法
CA2518318A1 (en) 2003-03-17 2004-09-30 Takeda San Diego, Inc. Histone deacetylase inhibitors
TW200424187A (en) 2003-04-04 2004-11-16 Hoffmann La Roche New oxime derivatives and their use as pharmaceutically active agents
SI1611088T1 (sl) 2003-04-07 2009-12-31 Pharmacyclics Inc Hidroksamati kot terapevtska sredstva
US20040220242A1 (en) * 2003-05-02 2004-11-04 Leland Shapiro Inhibitors of serine protease activity, methods and compositions for treatment of nitric oxide induced clinical conditions
CA2525251C (en) 2003-05-09 2015-10-27 Duke University Cd20-specific antibodies and methods employing same
CN1791396A (zh) 2003-05-21 2006-06-21 诺瓦提斯公司 组蛋白脱乙酰基酶抑制剂与化疗剂的组合
EP1491188A1 (en) * 2003-06-25 2004-12-29 G2M Cancer Drugs AG Topical use of valproic acid for the prevention or treatment of skin disorders
KR100924737B1 (ko) * 2003-08-26 2009-11-04 슬로안-케테링인스티튜트퍼캔서리서치 Hdac 억제제를 이용한 암의 치료 방법
CA2535889A1 (en) 2003-08-29 2005-03-17 Aton Pharma, Inc. Combination methods of treating cancer
EP1689445B1 (de) * 2003-11-14 2015-02-25 Per Sonne Holm Neue verwendung von adenoviren und dafür codierende nukleinsäuren
EP1689446B1 (de) * 2003-11-14 2015-01-07 Per Sonne Holm Neue adenoviren, dafür codierende nukleinsäuren und deren verwendung
US20070009956A1 (en) 2003-12-30 2007-01-11 Council Of Scientific And Industrial Research Arginine hydrochloride enhances chaperone-like activity of alpha crystallin
GB0401876D0 (en) * 2004-01-28 2004-03-03 Vereniging Het Nl Kanker I New use for cancer antigen
ATE437370T1 (de) * 2004-02-27 2009-08-15 Us Gov Health & Human Serv Pharmakodynamische tests mit durchflusszytometrie
ES2308065T3 (es) * 2004-04-30 2008-12-01 Topotarget Germany Ag Formulacion que comprende un inhibidor de histona desacetilasa, que exhibe una liberacion bifasica.
PL1781321T3 (pl) 2004-08-02 2014-07-31 Zenyth Operations Pty Ltd Sposób leczenia raka zawierający antagonistę VEGF-B
JPWO2006014024A1 (ja) * 2004-08-06 2008-05-01 小野薬品工業株式会社 精神神経系疾患治療剤
KR20070057822A (ko) * 2004-08-09 2007-06-07 아스텔라스세이야쿠 가부시키가이샤 히스톤 디아세틸라제 (hdac) 억제제 활성을 갖는히드록시아미드 화합물
WO2006060382A2 (en) * 2004-11-30 2006-06-08 Trustees Of The University Of Pennsylvania Use of hdac and/or dnmt inhibitors for treatment of ischemic injury
FR2879204B1 (fr) 2004-12-15 2007-02-16 Lab Francais Du Fractionnement Anticorps cytotoxique dirige contre les proliferations hematopoietiques lymphoides de type b.
EP1830864A2 (de) * 2004-12-31 2007-09-12 Per Sonne Holm E1 -minus adenoviren und deren verwendung
MX2007008781A (es) * 2005-01-21 2007-09-11 Astex Therapeutics Ltd Compuestos farmaceuticos.
NZ589276A (en) 2005-02-03 2012-06-29 Topotarget Uk Ltd Combination therapies using hdac inhibitors and erlotinib (tarceva)
US20060229237A1 (en) * 2005-04-07 2006-10-12 Yih-Lin Chung Treatment of gastrointestinal distress
GB0509225D0 (en) * 2005-05-05 2005-06-15 Chroma Therapeutics Ltd Inhibitors of enzymatic activity
CN101189003B (zh) 2005-05-13 2012-02-08 托波塔吉特英国有限公司 Hdac抑制剂的药物制剂
EP1743654A1 (en) * 2005-07-15 2007-01-17 TopoTarget Germany AG Use of inhibitors of histone deacetylases in combination with NSAID for the therapy of cancer and/or inflammatory diseases
US20080292616A1 (en) * 2005-08-19 2008-11-27 Government Of The United Of America, Represented By The Secretary, Department Of Health And.... Topical Formulations of Histone Deacetylase Inhibitors and Methods Using the Same
KR20080042170A (ko) * 2005-09-07 2008-05-14 플렉시콘, 인코퍼레이티드 Ppar 활성 화합물
WO2007049262A1 (en) 2005-10-27 2007-05-03 Berand Limited Methods and compositions for the promotion of neuronal growth and the treatment of asociality and affective disorders
JP5377968B2 (ja) * 2005-11-10 2013-12-25 トポターゲット ユーケー リミテッド 癌治療のために単独で用いるまたは化学療法薬と併用するヒストンデアセチラーゼ(hdac)阻害剤
US8445198B2 (en) * 2005-12-01 2013-05-21 Medical Prognosis Institute Methods, kits and devices for identifying biomarkers of treatment response and use thereof to predict treatment efficacy
EP3862354A1 (en) * 2006-02-22 2021-08-11 4Sc Ag Indolopyridines as eg5 kinesin modulators
MX2008010799A (es) * 2006-02-22 2008-11-06 4Sc Ag Indolopiridinas como moduladores de quinesina eg5.
GB0606096D0 (en) 2006-03-27 2006-05-03 Cbmm Sa Screening method
EP1839656A1 (en) * 2006-03-31 2007-10-03 TopoTarget Germany AG Use of valproic acid for the topical treatment of mild to moderate acne vulgaris
WO2007129062A1 (en) * 2006-05-08 2007-11-15 Astex Therapeutics Limited Pharmaceutical combinations of diazole derivatives for cancer treatment
EP2040731A4 (en) * 2006-06-09 2010-05-19 Merrion Res Iii Ltd SOLID DOSAGE FORM FOR ORAL ADMINISTRATION CONTAINING AN ACTIVATOR
US8338482B2 (en) * 2006-07-20 2012-12-25 Wisconsin Alumni Research Foundation Modulating notch1 signaling pathway for treating neuroendocrine tumors
WO2008058287A1 (en) * 2006-11-10 2008-05-15 Syndax Pharmaceuticals, Inc. COMBINATION OF ERα+ LIGANDS AND HISTONE DEACETYLASE INHIBITORS FOR THE TREATMENT OF CANCER
US8796330B2 (en) * 2006-12-19 2014-08-05 Methylgene Inc. Inhibitors of histone deacetylase and prodrugs thereof
WO2008090534A1 (en) 2007-01-26 2008-07-31 Berand Limited Methods and compositions for inhibition of excessive weight gain, reduction of inappropriate eating behaviours and inhibition of binge eating for the treatment of obesity
WO2008094319A2 (en) * 2007-02-01 2008-08-07 The Board Of Regents Of The University Of Texas Sytem Methods and compositions of trail-death receptor agonists/activators
WO2008101121A2 (en) * 2007-02-14 2008-08-21 Dana-Farber Cancer Institute, Inc. Methods and compositions relating to promoter regulation by muc1 and klf proteins
WO2008136838A1 (en) * 2007-05-04 2008-11-13 Trustees Of Dartmouth College Novel amide derivatives of cddo and methods of use thereof
EP2167090A4 (en) * 2007-06-06 2010-08-25 Univ Maryland HDAC INHIBITORS AND HORMONE TREATMENT MEDICAMENTS
WO2009146034A2 (en) * 2008-03-31 2009-12-03 Takeda Pharmaceutical Company Limited Mapk/erk kinase inhibitors and methods of use thereof
US20090270497A1 (en) * 2008-04-24 2009-10-29 Pharmacyclics, Inc. Treatment of Non-Localized Inflammation with pan-HDAC Inhibitors
WO2009137649A2 (en) * 2008-05-07 2009-11-12 The Trustees Of The University Of Pennsylvania Methods for treating thyroid cancer

Also Published As

Publication number Publication date
HK1145831A1 (en) 2011-05-06
CN101868446A (zh) 2010-10-20
MX2010003230A (es) 2010-04-07
JP2010540426A (ja) 2010-12-24
EP2203421B1 (en) 2014-05-07
US8642809B2 (en) 2014-02-04
EP2203421A2 (en) 2010-07-07
US20100286279A1 (en) 2010-11-11
WO2009040517A3 (en) 2009-06-25
WO2009040517A2 (en) 2009-04-02
CA2700173A1 (en) 2009-04-02

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