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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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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JP2009523822A5 (cg-RX-API-DMAC10.html
JP2009523822A (ja
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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    • 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)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Immunology (AREA)
  • Diabetes (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Cardiology (AREA)
  • Hematology (AREA)
  • Neurology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Hospice & Palliative Care (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Rheumatology (AREA)
  • Oncology (AREA)
  • Emergency Medicine (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Obesity (AREA)
  • Endocrinology (AREA)
  • Pain & Pain Management (AREA)
  • Communicable Diseases (AREA)
  • Psychiatry (AREA)
  • Transplantation (AREA)
  • Virology (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 (cg-RX-API-DMAC10.html) 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)

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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 (cg-RX-API-DMAC10.html)
EP (2) EP2474546A1 (cg-RX-API-DMAC10.html)
JP (2) JP5498703B2 (cg-RX-API-DMAC10.html)
CN (1) CN101400678A (cg-RX-API-DMAC10.html)
AU (1) AU2007208358A1 (cg-RX-API-DMAC10.html)
CA (1) CA2637335A1 (cg-RX-API-DMAC10.html)
WO (1) WO2007087283A2 (cg-RX-API-DMAC10.html)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MX2008003173A (es) 2005-09-06 2008-03-18 Smithkline Beecham Corp Compuestos de bencimidazol-tiofeno como inhibidores de plk.
EP2474546A1 (en) 2006-01-23 2012-07-11 Vertex Pharmaceuticals Inc. Thiophene-carboxamides useful as inhibitors of protein kinases
EP2007757B1 (en) * 2006-04-13 2012-10-03 Vertex Pharmceuticals Incorporated Thiophene-carboxamides useful as inhibitors of protein kinases
CA2652816A1 (en) * 2006-05-23 2007-12-06 Vertex Pharmaceuticals Incorporated Thiophene-carboxamides useful as inhibitors of protein kinases
JP2009538305A (ja) * 2006-05-23 2009-11-05 バーテックス ファーマシューティカルズ インコーポレイテッド 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
PE20080710A1 (es) * 2006-06-02 2008-08-07 Smithkline Beecham Corp Compuestos de tiofeno de bencimidazol
US7615643B2 (en) 2006-06-02 2009-11-10 Smithkline Beecham Corporation Benzimidazole thiophene compounds
CN101711245B (zh) 2007-07-19 2015-03-25 H.隆德贝克有限公司 5元杂环酰胺及相关的化合物
WO2010017046A1 (en) 2008-08-05 2010-02-11 Merck & Co., Inc. Pyrazolo[1,5-a]pyridines as mark inhibitors
PH12012500778A1 (en) 2009-10-30 2012-11-26 Janssen Pharmaceutica Nv IMIDAZO[1,2-b]PYRIDAZINE DERIVATIVES AND THEIR USE AS PDE10 INHIBITORS
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
CA2803446C (en) 2010-07-02 2019-06-04 University Health Network Use of plk4 antagonists for treating pten mutant diseases
JP6115962B2 (ja) 2011-06-27 2017-04-19 ヤンセン ファーマシューティカ エヌ.ベー. 1−アリール−4−メチル−[1,2,4]トリアゾロ[4,3−a]キノキサリン誘導体
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
CN116057045B (zh) 2020-06-05 2026-06-09 金耐特生物制药公司 成纤维细胞生长因子受体激酶抑制剂

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
AU726058B2 (en) 1995-09-01 2000-10-26 Signal Pharmaceuticals, Inc. Pyrimidine carboxylates and related compounds and methods for treating inflammatory conditions
EP0922043B1 (en) 1997-04-24 2002-01-30 Dow AgroSciences LLC Pesticidal 3-(substituted phenyl)-5-(thienyl or furyl)-1,2,4-triazoles
DE19744026A1 (de) 1997-10-06 1999-04-08 Hoechst Marion Roussel De Gmbh Pyrazol-Derivate, ihre Herstellung und ihre Verwendung in Arzneimitteln
PT957099E (pt) 1998-04-15 2003-02-28 Pfizer Prod Inc Carboxamidas heterociclicas
CN1136218C (zh) 1998-10-23 2004-01-28 道农业科学公司 制备3-(取代的苯基)-5-(噻吩基或呋喃基)-1,2,4-三唑的方法以及在其中使用的新中间体
AU2001245401A1 (en) 2000-03-01 2001-09-12 Sumitomo Pharmaceuticals Company, Limited Hydrazones and analogs as cholesterol lowering agents
US7273868B2 (en) 2000-04-28 2007-09-25 Tanabe Seiyaku Co., Ltd. Pyrazine derivatives
US7041685B2 (en) 2001-06-08 2006-05-09 Cytovia, Inc. Substituted 3-aryl-5-aryl-[1,2,4]-oxadiazoles and analogs as activators of caspases and inducers of apoptosis and the use thereof
AU2002356871A1 (en) 2001-10-30 2003-05-12 Pharmacia Corporation Heteroaromatic carboxamide derivatives for the treatment of inflammation
MXPA04000908A (es) 2002-05-30 2004-03-26 King Pharmaceuticals Res & Dev Compuestos farmaceuticamente activos que tienen estructura de anillo de pirazolotriazolopirimidina triciclica y metodos de uso.
MXPA05001544A (es) * 2002-08-08 2005-04-19 Smithkline Beecham Corp Compuestos de tiofeno.
JP2006516250A (ja) 2002-12-18 2006-06-29 サイトビア インコーポレイティッド カスパーゼ活性化剤およびアポトーシス誘導物質としての3,5−二置換−[1,2,4]−オキサジアゾールおよびそれらの誘導体ならびにそれらの使用
US7462614B2 (en) 2003-04-01 2008-12-09 Smithkline Beecham Corporation Imidazotriazine compounds
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
US20080293716A1 (en) 2004-01-30 2008-11-27 Smithkline Beecham Corporation Chemical Compounds
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
US7514448B2 (en) * 2004-04-02 2009-04-07 Vertex Pharmaceuticals Incorporated Azaindoles useful as inhibitors of rock and other protein kinases
WO2006049339A1 (ja) * 2004-11-08 2006-05-11 Banyu Pharmaceutical Co., Ltd. 新規縮環イミダゾール誘導体
AU2005316312B2 (en) 2004-12-17 2009-10-22 Amgen, Inc. Aminopyrimidine compounds and methods of use
EP1924572B1 (en) * 2005-09-06 2009-12-30 SmithKline Beecham Corporation Regioselective process for preparing benzimidazole thiophenes
EP2474546A1 (en) 2006-01-23 2012-07-11 Vertex Pharmaceuticals Inc. Thiophene-carboxamides useful as inhibitors of protein kinases
EP2007757B1 (en) 2006-04-13 2012-10-03 Vertex Pharmceuticals Incorporated Thiophene-carboxamides useful as inhibitors of protein kinases
JP2009538305A (ja) 2006-05-23 2009-11-05 バーテックス ファーマシューティカルズ インコーポレイテッド 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
CA2652816A1 (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
EP2474546A1 (en) 2012-07-11
WO2007087283A2 (en) 2007-08-02
JP2013056942A (ja) 2013-03-28
AU2007208358A1 (en) 2007-08-02
US8399478B2 (en) 2013-03-19
EP1989205B1 (en) 2012-06-13
US20110288095A1 (en) 2011-11-24
EP1989205A2 (en) 2008-11-12
CN101400678A (zh) 2009-04-01
US8759389B1 (en) 2014-06-24
JP2009523822A (ja) 2009-06-25
US20070219205A1 (en) 2007-09-20
WO2007087283A3 (en) 2007-09-13
US7915305B2 (en) 2011-03-29
CA2637335A1 (en) 2007-08-02

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