CA2532067C - N-methyle-substituted benzamidazoles - Google Patents

N-methyle-substituted benzamidazoles Download PDF

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Publication number
CA2532067C
CA2532067C CA2532067A CA2532067A CA2532067C CA 2532067 C CA2532067 C CA 2532067C CA 2532067 A CA2532067 A CA 2532067A CA 2532067 A CA2532067 A CA 2532067A CA 2532067 C CA2532067 C CA 2532067C
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CA
Canada
Prior art keywords
compound
alkyl
methyl
formula
fluoro
Prior art date
Legal status (The legal status 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 status listed.)
Expired - Fee Related
Application number
CA2532067A
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English (en)
French (fr)
Other versions
CA2532067A1 (en
Inventor
Stephen Douglas Barrett
Cathlin Marie Flamme
Michael David Kaufman
Jared Bruce John Milbank
Haile Tecle
Joseph Scott Warmus
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Warner Lambert Co LLC
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Warner Lambert Co LLC
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Publication date
Application filed by Warner Lambert Co LLC filed Critical Warner Lambert Co LLC
Publication of CA2532067A1 publication Critical patent/CA2532067A1/en
Application granted granted Critical
Publication of CA2532067C publication Critical patent/CA2532067C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/06—Antipsoriatics
    • 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
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • 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
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • 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
    • A61P35/00—Antineoplastic agents
    • 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
    • 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
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
    • 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
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/14—Radicals substituted by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic 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
    • C07D403/06—Heterocyclic 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 carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic 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
    • C07D403/12—Heterocyclic 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic 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
    • C07D405/02—Heterocyclic 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
    • C07D405/12—Heterocyclic 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Immunology (AREA)
  • Cardiology (AREA)
  • Rheumatology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pain & Pain Management (AREA)
  • Neurology (AREA)
  • Vascular Medicine (AREA)
  • Biomedical Technology (AREA)
  • Urology & Nephrology (AREA)
  • Neurosurgery (AREA)
  • Hospice & Palliative Care (AREA)
  • Dermatology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
CA2532067A 2003-07-24 2004-07-12 N-methyle-substituted benzamidazoles Expired - Fee Related CA2532067C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US49001203P 2003-07-24 2003-07-24
US60/490,012 2003-07-24
PCT/IB2004/002355 WO2005009975A2 (en) 2003-07-24 2004-07-12 Benzimidazole derivatives as mek inhibitors

Publications (2)

Publication Number Publication Date
CA2532067A1 CA2532067A1 (en) 2005-02-03
CA2532067C true CA2532067C (en) 2010-12-21

Family

ID=34102957

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2532067A Expired - Fee Related CA2532067C (en) 2003-07-24 2004-07-12 N-methyle-substituted benzamidazoles

Country Status (10)

Country Link
US (1) US7160915B2 (https=)
EP (1) EP1651214B1 (https=)
JP (1) JP4896717B2 (https=)
AT (1) ATE442847T1 (https=)
BR (1) BRPI0412851A (https=)
CA (1) CA2532067C (https=)
DE (1) DE602004023207D1 (https=)
ES (1) ES2331246T3 (https=)
MX (1) MXPA06000921A (https=)
WO (1) WO2005009975A2 (https=)

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US7235537B2 (en) * 2002-03-13 2007-06-26 Array Biopharma, Inc. N3 alkylated benzimidazole derivatives as MEK inhibitors
KR100984595B1 (ko) 2002-03-13 2010-09-30 어레이 바이오파마 인크. Ｍｅｋ 억제제로서의 ｎ3 알킬화 벤즈이미다졸 유도체
US7632866B2 (en) 2002-10-21 2009-12-15 Ramot At Tel Aviv University Derivatives of N-phenylanthranilic acid and 2-benzimidazolone as potassium channel and/or neuron activity modulators
CA2612419C (en) * 2005-06-23 2017-06-13 Array Biopharma Inc. Process for preparing benzimidazole compounds
AU2006262375A1 (en) * 2005-06-23 2007-01-04 Array Biopharma Inc. SNAr process for preparing benzimidazole compounds
US8101799B2 (en) * 2005-07-21 2012-01-24 Ardea Biosciences Derivatives of N-(arylamino) sulfonamides as inhibitors of MEK
US20070049591A1 (en) * 2005-08-25 2007-03-01 Kalypsys, Inc. Inhibitors of MAPK/Erk Kinase
SI1934174T1 (sl) 2005-10-07 2011-08-31 Exelixis Inc Inhibitorji MEK in postopki za njihovo uporabo
GB0601962D0 (en) 2006-01-31 2006-03-15 Ucb Sa Therapeutic agents
PL2101759T3 (pl) 2006-12-14 2019-05-31 Exelixis Inc Sposoby stosowania inhibitorów MEK
JO2985B1 (ar) 2006-12-20 2016-09-05 Takeda Pharmaceuticals Co مثبطات كينازmapk/erk
GB0714384D0 (en) 2007-07-23 2007-09-05 Ucb Pharma Sa theraputic agents
ATE551336T1 (de) * 2007-08-16 2012-04-15 Hoffmann La Roche Substituierte hydantoine
CN101868443A (zh) 2007-09-20 2010-10-20 特拉维夫大学拉莫特有限公司 N-苯基邻氨基苯甲酸衍生物及其用途
WO2009037705A2 (en) * 2007-09-20 2009-03-26 Ramot At Tel Aviv University Ltd. Esters of n-phenylanthranilic acid for use in the treatment of cancer and inflammation
ES2456966T3 (es) 2007-11-12 2014-04-24 Takeda Pharmaceutical Company Limited Inhibidores de MAPK/ERK cinasa
JP2011506533A (ja) 2007-12-20 2011-03-03 エフ．ホフマン−ラ ロシュ アーゲー Ｍｅｋキナーゼ阻害剤としての置換ヒダントイン
EP2240494B1 (en) 2008-01-21 2016-03-30 UCB Biopharma SPRL Thieno-pyridine derivatives as mek inhibitors
GB0811304D0 (en) 2008-06-19 2008-07-30 Ucb Pharma Sa Therapeutic agents
ES2426096T3 (es) * 2008-07-01 2013-10-21 Genentech, Inc. Derivados de isoindolona como inhibidores de la quinasa MEK y métodos de utilización
US8993630B2 (en) 2008-11-10 2015-03-31 Bayer Intellectual Property Gmbh Substituted sulphonamido phenoxybenzamides
WO2010068738A1 (en) 2008-12-10 2010-06-17 Dana-Farber Cancer Institute, Inc. Mek mutations conferring resistance to mek inhibitors
WO2010143733A1 (en) 2009-06-09 2010-12-16 Takeda Pharmaceutical Company Limited Novel fused cyclic compound and use thereof
US20120269803A1 (en) 2009-10-21 2012-10-25 Bayer Intellectual Property Gmbh Substituted benzosulphonamides
EP2491014A1 (en) 2009-10-21 2012-08-29 Bayer Pharma Aktiengesellschaft Substituted halophenoxybenzamide derivatives
EP2491015A1 (en) 2009-10-21 2012-08-29 Bayer Pharma Aktiengesellschaft Substituted benzosulphonamides
ES2576061T3 (es) 2010-02-25 2016-07-05 Dana-Farber Cancer Institute, Inc. Mutaciones de BRAF que confieren resistencia a inhibidores de BRAF
BR112012022801B8 (pt) 2010-03-09 2019-10-29 Dana Farber Cancer Inst Inc método de identificar um indivíduo que tem câncer que é provável beneficiar-se do tratamento com uma terapia de combinação com um inibidor de raf e um segundo inibidor e uso de um inibidor de raf e um segundo inibidor para a fabricação de um medicamento para tratar câncer
WO2012055953A1 (en) 2010-10-29 2012-05-03 Bayer Pharma Aktiengesellschaft Substituted phenoxypyridines
CN103204825B (zh) 2012-01-17 2015-03-04 上海科州药物研发有限公司 作为蛋白激酶抑制剂的苯并噻唑化合物及其制备方法和用途
US20150141470A1 (en) 2012-05-08 2015-05-21 The Broad Institute, Inc. Diagnostic and treatment methods in patients having or at risk of developing resistance to cancer therapy
JP2015527874A (ja) 2012-05-31 2015-09-24 バイエル ファーマ アクチエンゲゼルシャフト 肝細胞癌（ｈｃｃ）患者の治療の有効な応答を決定するためのバイオマーカー
KR102204520B1 (ko) 2012-10-12 2021-01-20 엑셀리시스, 인코포레이티드 암의 치료에 사용하기 위한 화합물의 신규 제조 방법
FI3702351T3 (fi) * 2012-10-19 2024-01-24 Array Biopharma Inc MEK-inhibiittorin käsittävä koostumus
CN111518031B (zh) * 2020-05-29 2023-01-17 中国药科大学 一种含有异羟肟酸的化合物及其制备方法、应用

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IL144214A0 (en) 1999-01-13 2002-05-23 Warner Lambert Co Benzoheterocycles and their use as mek inhibitors
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US7235537B2 (en) 2002-03-13 2007-06-26 Array Biopharma, Inc. N3 alkylated benzimidazole derivatives as MEK inhibitors

Also Published As

Publication number Publication date
US7160915B2 (en) 2007-01-09
BRPI0412851A (pt) 2006-10-03
US20050026970A1 (en) 2005-02-03
ES2331246T3 (es) 2009-12-28
WO2005009975A3 (en) 2005-04-07
MXPA06000921A (es) 2006-03-30
CA2532067A1 (en) 2005-02-03
WO2005009975A2 (en) 2005-02-03
DE602004023207D1 (de) 2009-10-29
JP4896717B2 (ja) 2012-03-14
EP1651214A2 (en) 2006-05-03
ATE442847T1 (de) 2009-10-15
JP2006528621A (ja) 2006-12-21
EP1651214B1 (en) 2009-09-16

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