CA2463598C - Imidazo (4,3-e)-1,2,4-triazolo(1,5-c) pyrimidines as adenosine a2a receptor antagonists - Google Patents

Imidazo (4,3-e)-1,2,4-triazolo(1,5-c) pyrimidines as adenosine a2a receptor antagonists Download PDF

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Publication number
CA2463598C
CA2463598C CA002463598A CA2463598A CA2463598C CA 2463598 C CA2463598 C CA 2463598C CA 002463598 A CA002463598 A CA 002463598A CA 2463598 A CA2463598 A CA 2463598A CA 2463598 C CA2463598 C CA 2463598C
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CA
Canada
Prior art keywords
alkyl
alkoxy
phenyl
compound
heteroaryl
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
CA002463598A
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English (en)
French (fr)
Other versions
CA2463598A1 (en
Inventor
Deen Tulshian
Lisa S. Silverman
Julius J. Matasi
Eugenia Y. Kiselgof
John P. Caldwell
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Merck Sharp and Dohme LLC
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Schering Corp
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Publication of CA2463598C publication Critical patent/CA2463598C/en
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    • 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
    • C07D487/12—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 three hetero rings
    • C07D487/14—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
    • A61K31/198—Alpha-amino acids, e.g. alanine or edetic acid [EDTA]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • 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
    • A61P25/24—Antidepressants
    • 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
    • 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
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/582—Recycling of unreacted starting or intermediate materials

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Neurology (AREA)
  • Epidemiology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Psychiatry (AREA)
  • Vascular Medicine (AREA)
  • Pain & Pain Management (AREA)
  • Psychology (AREA)
  • Hospice & Palliative Care (AREA)
  • Urology & Nephrology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
CA002463598A 2001-10-15 2002-10-11 Imidazo (4,3-e)-1,2,4-triazolo(1,5-c) pyrimidines as adenosine a2a receptor antagonists Expired - Fee Related CA2463598C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US32956701P 2001-10-15 2001-10-15
US60/329,567 2001-10-15
PCT/US2002/032630 WO2003032996A1 (en) 2001-10-15 2002-10-11 Imidazo (4,3-e)-1,2,4-triazolo(1,5-c) pyrimidines as adenosine a2a receptor antagonists

Publications (2)

Publication Number Publication Date
CA2463598A1 CA2463598A1 (en) 2003-04-24
CA2463598C true CA2463598C (en) 2009-09-08

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CA002463598A Expired - Fee Related CA2463598C (en) 2001-10-15 2002-10-11 Imidazo (4,3-e)-1,2,4-triazolo(1,5-c) pyrimidines as adenosine a2a receptor antagonists

Country Status (16)

Country Link
US (1) US6653315B2 (enExample)
EP (1) EP1435960B1 (enExample)
JP (2) JP4545437B2 (enExample)
KR (1) KR100687954B1 (enExample)
CN (1) CN100421663C (enExample)
AR (1) AR037243A1 (enExample)
AU (1) AU2002340184B2 (enExample)
CA (1) CA2463598C (enExample)
HU (1) HUP0401777A3 (enExample)
IL (1) IL160878A0 (enExample)
MX (1) MXPA04003474A (enExample)
MY (1) MY124864A (enExample)
NZ (1) NZ531761A (enExample)
PE (1) PE20030477A1 (enExample)
WO (1) WO2003032996A1 (enExample)
ZA (1) ZA200402812B (enExample)

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DE60335294D1 (de) 2002-12-19 2011-01-20 Schering Corp Dlung des extrapyramidalen syndroms
NZ542823A (en) 2003-04-23 2009-03-31 Schering Corp 2-Alkynyl- and 2-alkenyl-pyrazolo-[4,3-e]-1,2,4-triazolo-[1,5-c]-pyrimidine adenosine A2a receptor antagonists
CN1787821A (zh) * 2003-06-10 2006-06-14 协和发酵工业株式会社 一种治疗焦虑症的方法
MXPA06007102A (es) * 2003-12-19 2006-08-23 Schering Corp Composiciones farmaceuticas.
NZ550591A (en) 2004-04-21 2010-10-29 Schering Corp Pyrazolo-[4,3-e]-1,2,4-triazolo-[1,5-c]-pyrimidine adenosine A2A receptor antagonists
ES2385702T3 (es) 2005-06-07 2012-07-30 Kyowa Hakko Kirin Co., Ltd. Antagonistas de A2A para uso en el tratamiento de trastornos de la motricidad
AR057817A1 (es) * 2005-09-19 2007-12-19 Schering Corp Antagonistas del receptor a2a de 2-heteroaril-pirazolo-[4,3-e]-1,2,4-triazolo-[1,5-c]-pirimidin adenosina. composiciones farmaceuticas
AR056080A1 (es) * 2005-09-23 2007-09-19 Schering Corp 7-[2-[4-(6-fluoro-3-metil-1,2-benciosoxazol-5-il)-1-piperazinil]etil]-2-(1-propinil)-7h-pirazol-[4,3-e]-[1,2,4]-triazol-[1,5-c] -pirimidin-5-amine
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CA2715290A1 (en) * 2008-02-15 2009-08-20 Vitae Pharmaceuticals, Inc. Inhibitors of 11beta-hydroxysteroid dehydrogenase 1
JP2011513417A (ja) 2008-03-04 2011-04-28 シェーリング コーポレイション アデノシンＡ２ａ受容体アンタゴニストとして使用するための１，２，４−トリアゾロ［４，３−ｃ］ピリミジン−３−オンおよびピラゾロ［４，３−ｅ］−１，２，４−トリアゾロ［４，３−ｃ］ピリミジン−３−オン化合物
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Also Published As

Publication number Publication date
AU2002340184B2 (en) 2005-10-06
MXPA04003474A (es) 2004-07-30
HUP0401777A2 (hu) 2004-12-28
KR20050035155A (ko) 2005-04-15
ZA200402812B (en) 2005-04-25
IL160878A0 (en) 2004-08-31
KR100687954B1 (ko) 2007-02-27
JP2008297312A (ja) 2008-12-11
JP2005506352A (ja) 2005-03-03
CA2463598A1 (en) 2003-04-24
AR037243A1 (es) 2004-11-03
EP1435960B1 (en) 2014-07-30
PE20030477A1 (es) 2003-06-06
WO2003032996A1 (en) 2003-04-24
JP4545437B2 (ja) 2010-09-15
CN1612736A (zh) 2005-05-04
HUP0401777A3 (en) 2008-06-30
CN100421663C (zh) 2008-10-01
US20030171381A1 (en) 2003-09-11
MY124864A (en) 2006-07-31
NZ531761A (en) 2005-10-28
EP1435960A1 (en) 2004-07-14
US6653315B2 (en) 2003-11-25

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