JP5498703B2 - プロテインキナーゼのインヒビターとして有用なチオフェン−カルボキサミド - Google Patents

プロテインキナーゼのインヒビターとして有用なチオフェン−カルボキサミド Download PDF

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Publication number
JP5498703B2
JP5498703B2 JP2008551474A JP2008551474A JP5498703B2 JP 5498703 B2 JP5498703 B2 JP 5498703B2 JP 2008551474 A JP2008551474 A JP 2008551474A JP 2008551474 A JP2008551474 A JP 2008551474A JP 5498703 B2 JP5498703 B2 JP 5498703B2
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Japan
Prior art keywords
compound
ring
formula
alkyl
alkenyl
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Expired - Fee Related
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JP2008551474A
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Japanese (ja)
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JP2009523822A (ja
JP2009523822A5 (https=
Inventor
スティーブン デュラント，
ジャン−ダミアン シャリエ，
ロナルド ネグテル，
ガイ ブレンチリー，
デイビッド ケイ，
シャジア サディック，
シャーン ラマヤ，
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Vertex Pharmaceuticals Inc
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Vertex Pharmaceuticals Inc
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Immunology (AREA)
  • Diabetes (AREA)
  • Neurosurgery (AREA)
  • Hematology (AREA)
  • Cardiology (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Hospice & Palliative Care (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Rheumatology (AREA)
  • Oncology (AREA)
  • Obesity (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Virology (AREA)
  • Transplantation (AREA)
  • Psychiatry (AREA)
  • Pain & Pain Management (AREA)
  • Endocrinology (AREA)
  • Communicable Diseases (AREA)
  • Emergency Medicine (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
JP2008551474A 2006-01-23 2007-01-23 プロテインキナーゼのインヒビターとして有用なチオフェン−カルボキサミド Expired - Fee Related JP5498703B2 (ja)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US76109706P 2006-01-23 2006-01-23
US60/761,097 2006-01-23
PCT/US2007/001726 WO2007087283A2 (en) 2006-01-23 2007-01-23 Thiophene-carboxamides useful as inhibitors of protein kinases

Related Child Applications (1)

Application Number Title Priority Date Filing Date
JP2012281195A Division JP2013056942A (ja) 2006-01-23 2012-12-25 プロテインキナーゼのインヒビターとして有用なチオフェン−カルボキサミド

Publications (3)

Publication Number Publication Date
JP2009523822A JP2009523822A (ja) 2009-06-25
JP2009523822A5 JP2009523822A5 (https=) 2011-03-10
JP5498703B2 true JP5498703B2 (ja) 2014-05-21

Family

ID=38179584

Family Applications (2)

Application Number Title Priority Date Filing Date
JP2008551474A Expired - Fee Related JP5498703B2 (ja) 2006-01-23 2007-01-23 プロテインキナーゼのインヒビターとして有用なチオフェン−カルボキサミド
JP2012281195A Pending JP2013056942A (ja) 2006-01-23 2012-12-25 プロテインキナーゼのインヒビターとして有用なチオフェン−カルボキサミド

Family Applications After (1)

Application Number Title Priority Date Filing Date
JP2012281195A Pending JP2013056942A (ja) 2006-01-23 2012-12-25 プロテインキナーゼのインヒビターとして有用なチオフェン−カルボキサミド

Country Status (7)

Country Link
US (3) US7915305B2 (https=)
EP (2) EP2474546A1 (https=)
JP (2) JP5498703B2 (https=)
CN (1) CN101400678A (https=)
AU (1) AU2007208358A1 (https=)
CA (1) CA2637335A1 (https=)
WO (1) WO2007087283A2 (https=)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EA014111B1 (ru) 2005-09-06 2010-10-29 Смитклайн Бичем Корпорейшн Бензимидазолтиофеновые соединения в качестве ингибиторов polo-подобных киназ (plk)
EP2474546A1 (en) 2006-01-23 2012-07-11 Vertex Pharmaceuticals Inc. Thiophene-carboxamides useful as inhibitors of protein kinases
WO2007120760A2 (en) 2006-04-13 2007-10-25 Vertex Pharmaceuticals Incorporated Thiophene-carboxamides useful as inhibitors of protein kinases
WO2007139795A1 (en) * 2006-05-23 2007-12-06 Vertex Pharmaceuticals Incorporated Thiophene-carboxamides useful as inhibitors of protein kinases
WO2007139816A2 (en) * 2006-05-23 2007-12-06 Vertex Pharmaceuticals Incorporated Thiophene-carboxamides useful as inhibitors of protein kinases
US7615643B2 (en) 2006-06-02 2009-11-10 Smithkline Beecham Corporation Benzimidazole thiophene compounds
EP2032563B1 (en) * 2006-06-02 2010-06-02 GlaxoSmithKline LLC Benzimidazol substituted thiophene derivatives with activity on plk
HRP20151052T1 (xx) 2007-07-19 2015-11-06 H. Lundbeck A/S Peteroäślani heterocikliäśki amidi i srodne tvari
US8518911B2 (en) 2008-08-05 2013-08-27 Merck Sharp & Dohme Corp. Pyrazolo[1,5-a]pyridines as MARK inhibitors
KR101774035B1 (ko) 2009-10-30 2017-09-01 얀센 파마슈티카 엔.브이. 이미다조［１，２―ｂ］피리다진 유도체 및 ＰＤＥ１０ 저해제로서의 그의 용도
AR080754A1 (es) 2010-03-09 2012-05-09 Janssen Pharmaceutica Nv Derivados de imidazo (1,2-a) pirazina y su uso como inhibidores de pde10
ES2706066T3 (es) 2010-07-02 2019-03-27 Univ Health Network Procedimiento dirigido a enfermedades mutantes con PTEN y composiciones para las mismas
WO2013000924A1 (en) 2011-06-27 2013-01-03 Janssen Pharmaceutica Nv 1-ARYL-4-METHYL-[1,2,4]TRIAZOLO[4,3-a]QUINOXALINE DERIVATIVES
JO3407B1 (ar) 2012-05-31 2019-10-20 Eisai R&D Man Co Ltd مركبات رباعي هيدرو بيرازولو بيريميدين
WO2014001314A1 (en) 2012-06-26 2014-01-03 Janssen Pharmaceutica Nv Combinations comprising pde 2 inhibitors such as 1-aryl-4-methyl- [1,2,4] triazolo [4,3-a] quinoxaline compounds and pde 10 inhibitors for use in the treatment of neurological or metabolic disorders
AU2013289284B2 (en) 2012-07-09 2017-03-30 Janssen Pharmaceutica Nv Inhibitors of phosphodiesterase 10 enzyme
EP3310360B1 (en) * 2015-06-19 2024-03-27 Beijing Artivila BioPharma Co. Ltd. Chiral specific boron-containing compounds and their use in treating cancer or amyloidosis
WO2018081719A1 (en) * 2016-10-31 2018-05-03 Arizona Board Of Regents On Behalf Of The University Of Arizona Small molecule inhibitors of nek2 and uses thereof
US11345681B1 (en) 2020-06-05 2022-05-31 Kinnate Biopharma Inc. Inhibitors of fibroblast growth factor receptor kinases

Family Cites Families (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1255802B (it) 1992-08-07 1995-11-16 Luso Farmaco Inst Derivati imidazolici ad attivita' a ii antagonista
WO1997009325A1 (en) 1995-09-01 1997-03-13 Signal Pharmaceuticals, Inc. Pyrimidine carboxylates and related compounds and methods for treating inflammatory conditions
ES2167882T3 (es) 1997-04-24 2002-05-16 Dow Agrosciences Llc 3-(fenil sustituido)-5-(tienil o furil)-1,2,4-triazoles pesticidas.
DE19744026A1 (de) * 1997-10-06 1999-04-08 Hoechst Marion Roussel De Gmbh Pyrazol-Derivate, ihre Herstellung und ihre Verwendung in Arzneimitteln
DE69903992T2 (de) 1998-04-15 2003-08-21 Pfizer Products Inc., Groton Heterocyclische Carboxamide
DK1123291T3 (da) 1998-10-23 2007-11-05 Dow Agrosciences Llc Fremgangsmåde til fremstilling af 3-(substitueret phenyl)-5-thienyl (eller furyl)-1,2,4-triazoler og hidtil ukendte mellemprodukter anvendt derved
US6605615B2 (en) 2000-03-01 2003-08-12 Tularik Inc. Hydrazones and analogs as cholesterol lowering agents
US7273868B2 (en) * 2000-04-28 2007-09-25 Tanabe Seiyaku Co., Ltd. Pyrazine derivatives
JP2005504014A (ja) 2001-06-08 2005-02-10 サイトビア インコーポレイテッド カスパーゼの活性化因子およびアポトーシスの誘導因子としての置換された３−アリール−５−アリール−［１，２，４］−オキサジアゾール類および類似体、並びにその使用法
JP2005509645A (ja) 2001-10-30 2005-04-14 ファルマシア・コーポレーション 炎症処置用のヘテロ芳香族カルボキサミド誘導体
AU2003245380A1 (en) 2002-05-30 2003-12-19 King Pharmaceuticals Research & Development, Inc. Pharmaceutically active compounds having a tricyclic pyrazolotriazolopyrimidine ring structure and methods of use
BR0313160A (pt) 2002-08-08 2005-07-12 Smithkline Beecham Corp Composto, composição farmacêutica, métodos para tratar uma condição e um neoplasmo suscetìvel em um animal em um animal, processo para preparar um composto e uso de um composto
CN100364531C (zh) 2002-12-18 2008-01-30 西托维亚公司 3,5－二取代－[1,2,4]－二唑及类似物和其用途
JP2006522127A (ja) * 2003-04-01 2006-09-28 スミスクライン ビーチャム コーポレーション イミダゾトリアジン化合物
US20050090529A1 (en) * 2003-07-31 2005-04-28 Pfizer Inc 3,5 Disubstituted indazole compounds with nitrogen-bearing 5-membered heterocycles, pharmaceutical compositions, and methods for mediating or inhibiting cell proliferation
EP1685128A1 (en) 2003-10-16 2006-08-02 Smithkline Beecham Corporation Process for preparing benzimidazole thiophenes
JP2007519753A (ja) 2004-01-30 2007-07-19 スミスクライン ビーチャム コーポレーション 化合物
GB0402809D0 (en) 2004-02-09 2004-03-10 Glaxo Group Ltd Chemical compounds
WO2005095386A1 (en) 2004-03-30 2005-10-13 Chiron Corporation Substituted thiophene derivatives as anti-cancer agents
AR049333A1 (es) 2004-04-02 2006-07-19 Vertex Pharma Azaindoles inhibidores de proteinquinasas rock y otras proteinas quinasas. composiciones farmaceuticas.
JP4935357B2 (ja) * 2004-11-08 2012-05-23 Ｍｓｄ株式会社 新規縮環イミダゾール誘導体
EP1831207B1 (en) 2004-12-17 2012-11-14 Amgen Inc. Aminopyrimidine compounds as plk inhibitors
MX2008003172A (es) * 2005-09-06 2008-03-18 Smithkline Beecham Corp Proceso regioselectivo para la preparacion de bencimidazol-tiofenos.
EP2474546A1 (en) 2006-01-23 2012-07-11 Vertex Pharmaceuticals Inc. Thiophene-carboxamides useful as inhibitors of protein kinases
WO2007120760A2 (en) 2006-04-13 2007-10-25 Vertex Pharmaceuticals Incorporated Thiophene-carboxamides useful as inhibitors of protein kinases
WO2007139795A1 (en) 2006-05-23 2007-12-06 Vertex Pharmaceuticals Incorporated Thiophene-carboxamides useful as inhibitors of protein kinases
WO2007139816A2 (en) 2006-05-23 2007-12-06 Vertex Pharmaceuticals Incorporated Thiophene-carboxamides useful as inhibitors of protein kinases

Also Published As

Publication number Publication date
AU2007208358A1 (en) 2007-08-02
JP2009523822A (ja) 2009-06-25
JP2013056942A (ja) 2013-03-28
CA2637335A1 (en) 2007-08-02
WO2007087283A3 (en) 2007-09-13
WO2007087283A2 (en) 2007-08-02
EP1989205A2 (en) 2008-11-12
EP2474546A1 (en) 2012-07-11
CN101400678A (zh) 2009-04-01
US7915305B2 (en) 2011-03-29
US20070219205A1 (en) 2007-09-20
US8759389B1 (en) 2014-06-24
US20110288095A1 (en) 2011-11-24
US8399478B2 (en) 2013-03-19
EP1989205B1 (en) 2012-06-13

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