CA2523245C - Indole acetic acid derivatives and their use as pharmaceutical agents - Google Patents

Indole acetic acid derivatives and their use as pharmaceutical agents Download PDF

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Publication number
CA2523245C
CA2523245C CA2523245A CA2523245A CA2523245C CA 2523245 C CA2523245 C CA 2523245C CA 2523245 A CA2523245 A CA 2523245A CA 2523245 A CA2523245 A CA 2523245A CA 2523245 C CA2523245 C CA 2523245C
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CA
Canada
Prior art keywords
propoxy
cndot
phenoxy
indol
acetic acid
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
CA2523245A
Other languages
English (en)
French (fr)
Other versions
CA2523245A1 (en
Inventor
Xin Ma
Louis-David Cantin
Soongyu Choi
Roger Clark
Martin Hentemann
Joachim Rudolph
Rico Lavoie
Zhonghua Zhang
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer Healthcare LLC
Original Assignee
Bayer Healthcare LLC
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 Bayer Healthcare LLC filed Critical Bayer Healthcare LLC
Publication of CA2523245A1 publication Critical patent/CA2523245A1/en
Application granted granted Critical
Publication of CA2523245C publication Critical patent/CA2523245C/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
    • 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
    • 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
    • A61P3/04—Anorexiants; Antiobesity agents
    • 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
    • A61P3/06—Antihyperlipidemics
    • 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
    • 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
    • A61P35/00—Antineoplastic agents
    • 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
    • A61P9/10—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
    • 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
    • A61P9/12—Antihypertensives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic 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
    • C07D401/02—Heterocyclic 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
    • C07D401/12—Heterocyclic 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
    • 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
    • C07D405/14—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 three or more hetero rings
    • 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
    • C07D413/12—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 linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (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)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Emergency Medicine (AREA)
  • Endocrinology (AREA)
  • Vascular Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Child & Adolescent Psychology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Indole Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
CA2523245A 2003-04-28 2004-04-28 Indole acetic acid derivatives and their use as pharmaceutical agents Expired - Fee Related CA2523245C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US46614303P 2003-04-28 2003-04-28
US60/466,143 2003-04-28
PCT/US2004/012959 WO2004098498A2 (en) 2003-04-28 2004-04-28 Indole acetic acid derivatives and their use as pharmaceutical agents

Publications (2)

Publication Number Publication Date
CA2523245A1 CA2523245A1 (en) 2004-11-18
CA2523245C true CA2523245C (en) 2012-03-06

Family

ID=33434943

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2523245A Expired - Fee Related CA2523245C (en) 2003-04-28 2004-04-28 Indole acetic acid derivatives and their use as pharmaceutical agents

Country Status (5)

Country Link
US (2) US7592361B2 (enExample)
EP (1) EP1620088A4 (enExample)
JP (2) JP4828414B2 (enExample)
CA (1) CA2523245C (enExample)
WO (1) WO2004098498A2 (enExample)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7820837B2 (en) 2003-05-30 2010-10-26 Takeda Pharmaceutical Company Limited Condensed ring compound
JP4805552B2 (ja) * 2003-05-30 2011-11-02 武田薬品工業株式会社 縮合環化合物
US9408405B2 (en) 2003-10-03 2016-08-09 Veijlen N.V. Use of compounds that are able to increase the serum IGF-1 level for the preparation of a therapeutical composition for treatment of various disease states associated with a reduced IGF-1 serum level in humans and animals
US7622491B2 (en) * 2004-08-13 2009-11-24 Metabolex Inc. Modulators of PPAR and methods of their preparation
CA2602336A1 (en) * 2005-03-31 2006-10-05 Ucb Pharma S.A. Compounds comprising an oxazole or thiazole moiety, processes for making them, and their uses
WO2013042782A1 (ja) 2011-09-22 2013-03-28 武田薬品工業株式会社 縮合複素環化合物
KR101808196B1 (ko) * 2016-01-08 2017-12-14 대한민국(농촌진흥청장) 왕지네 유래 신규 화합물 및 이의 항혈전 용도
CN106702003B (zh) * 2017-02-28 2021-02-12 固安博健生物技术有限公司 Hsdl1在诊治骨肉瘤中的应用
CN117326903B (zh) * 2023-09-27 2025-05-02 常州大学 一种高立体选择性合成n-烷基化吲哚衍生物的方法

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2203517A1 (en) * 1994-11-10 1996-05-23 Alan M. Laibelman Pharmaceutical pyrazole compositions useful as inhibitors of protein kinases
AP2000001929A0 (en) * 1998-03-31 2000-09-30 Inst For Pharm Discovery Inc Substituted indolealkanoic acids.
GB9820113D0 (en) * 1998-09-15 1998-11-11 Merck Sharp & Dohme Therapeutic agents
TNSN99224A1 (fr) * 1998-12-01 2005-11-10 Inst For Pharm Discovery Inc Methodes de reduction des niveaux de glucose et triglyceride en serum et pour suppression de l'antigenese utilisant les acides la indolealkanoique
DE10006139A1 (de) * 2000-02-11 2001-08-16 Merck Patent Gmbh Indol-3-yl-Derivate
EP1305394A1 (en) * 2000-07-19 2003-05-02 The Procter & Gamble Company Gel form automatic dishwashing compositions, methods of preparation and use thereof
JP2004521079A (ja) * 2000-08-29 2004-07-15 ファルマシア・コーポレーション アルファーｖベータ３アンタゴニストとして有用な二環式環系を含有する化合物
WO2002060438A1 (en) * 2001-01-29 2002-08-08 3-Dimensional Pharmaceuticals, Inc. Substituted indoles and their use as integrin antagonists
JP2005504778A (ja) * 2001-08-29 2005-02-17 ワーナー−ランバート・カンパニー、リミテッド、ライアビリティ、カンパニー 経口抗糖尿病剤
CA2521135A1 (en) * 2003-04-07 2004-10-28 Kalypsys, Inc. N-containing heteroaromatic compounds as modulators of ppars and methods of treating metabolic disorders

Also Published As

Publication number Publication date
US20090298854A1 (en) 2009-12-03
EP1620088A4 (en) 2007-08-29
WO2004098498A3 (en) 2005-07-28
CA2523245A1 (en) 2004-11-18
JP2011063613A (ja) 2011-03-31
JP2006524709A (ja) 2006-11-02
US7964622B2 (en) 2011-06-21
US7592361B2 (en) 2009-09-22
US20060264486A1 (en) 2006-11-23
JP4828414B2 (ja) 2011-11-30
WO2004098498A2 (en) 2004-11-18
EP1620088A2 (en) 2006-02-01

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Effective date: 20140429