CA2468658C - [1,2,4]-triazole bicyclic adenosine a2a receptor antagonists - Google Patents

[1,2,4]-triazole bicyclic adenosine a2a receptor antagonists Download PDF

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Publication number
CA2468658C
CA2468658C CA002468658A CA2468658A CA2468658C CA 2468658 C CA2468658 C CA 2468658C CA 002468658 A CA002468658 A CA 002468658A CA 2468658 A CA2468658 A CA 2468658A CA 2468658 C CA2468658 C CA 2468658C
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CA
Canada
Prior art keywords
alkyl
concentrate
compound
product
add
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
CA002468658A
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English (en)
French (fr)
Other versions
CA2468658A1 (en
Inventor
Bernard R. Neustadt
Hong Liu
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.)
Merck Sharp and Dohme LLC
Original Assignee
Schering Corp
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Filing date
Publication date
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Publication of CA2468658A1 publication Critical patent/CA2468658A1/en
Application granted granted Critical
Publication of CA2468658C publication Critical patent/CA2468658C/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
    • 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
    • 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
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • 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
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • 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

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  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Psychiatry (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Pain & Pain Management (AREA)
  • Psychology (AREA)
  • Hospice & Palliative Care (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
CA002468658A 2001-11-30 2002-11-26 [1,2,4]-triazole bicyclic adenosine a2a receptor antagonists Expired - Fee Related CA2468658C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US33438501P 2001-11-30 2001-11-30
US60/334,385 2001-11-30
PCT/US2002/037915 WO2003048163A1 (en) 2001-11-30 2002-11-26 [1,2,4]-TRIAZOLE BICYCLIC ADENOSINE A2a RECEPTOR ANTAGONISTS

Publications (2)

Publication Number Publication Date
CA2468658A1 CA2468658A1 (en) 2003-06-12
CA2468658C true CA2468658C (en) 2009-04-14

Family

ID=23306955

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002468658A Expired - Fee Related CA2468658C (en) 2001-11-30 2002-11-26 [1,2,4]-triazole bicyclic adenosine a2a receptor antagonists

Country Status (18)

Country Link
US (2) US6875772B2 (enExample)
EP (1) EP1453836B1 (enExample)
JP (2) JP4429724B2 (enExample)
KR (1) KR20050044600A (enExample)
CN (1) CN1688581A (enExample)
AR (1) AR037681A1 (enExample)
AT (1) ATE358130T1 (enExample)
AU (1) AU2002352933A1 (enExample)
CA (1) CA2468658C (enExample)
DE (1) DE60219196T2 (enExample)
ES (1) ES2283625T3 (enExample)
HU (1) HUP0402324A3 (enExample)
IL (1) IL161573A0 (enExample)
MX (1) MXPA04005158A (enExample)
PE (1) PE20030653A1 (enExample)
TW (1) TW200300689A (enExample)
WO (1) WO2003048163A1 (enExample)
ZA (1) ZA200404168B (enExample)

Families Citing this family (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MXPA04005158A (es) * 2001-11-30 2004-08-11 Schering Corp Antagonistas receptores de adenosina a2a biciclica de (1.2.4]- triazol.
PE20030739A1 (es) 2001-11-30 2003-08-28 Schering Corp Antagonistas del receptor de adenosina a2a
TW200304825A (en) * 2002-03-12 2003-10-16 Wyeth Corp Process for making chiral 1,4-disubstituted piperazines
WO2004029056A1 (ja) * 2002-09-24 2004-04-08 Kyowa Hakko Kogyo Co., Ltd. [１，２，４]トリアゾロ[１，５−ｃ]ピリミジン誘導体
WO2005044245A1 (en) * 2002-12-19 2005-05-19 Schering Corporation USES OF ADENOSINE A2a RECEPTOR ANTAGONISTS
US7285550B2 (en) 2003-04-09 2007-10-23 Biogen Idec Ma Inc. Triazolotriazines and pyrazolotriazines and methods of making and using the same
EP1618109A2 (en) * 2003-04-09 2006-01-25 Biogen Idec MA Inc. Triazolo[1,5-c]pyrimidines and pyrazolo[1,5-c]pyrimidines useful as a2a adenosine receptor antagonists
EP1633756B1 (en) 2003-04-09 2008-12-24 Biogen Idec MA Inc. A2a adenosine receptor antagonists
WO2004092177A1 (en) 2003-04-09 2004-10-28 Biogen Idec Ma Inc. Triazolopyrazines and methods of making and using the same
TW200507850A (en) 2003-07-25 2005-03-01 Kyowa Hakko Kogyo Kk Pharmaceutical composition
WO2006129626A1 (ja) * 2005-05-30 2006-12-07 Kyowa Hakko Kogyo Co., Ltd. [1,2,4]トリアゾロ[1,5-c]ピリミジン誘導体の製造法
EP2258372B8 (en) 2005-06-07 2012-12-19 Kyowa Hakko Kirin Co., Ltd. A2A antagonists for use in the treatment of motor disorders
WO2006131524A1 (en) * 2005-06-08 2006-12-14 Neurosearch A/S Novel n-phenyl-piperidine derivatives and their use as monoamine neurotransmitter re-uptake inhibitors
WO2007027987A2 (en) * 2005-09-02 2007-03-08 Mount Cook Biosciences, Inc. Method of treating parkinson's disease with diarylmethylpiperazine compounds exhibiting delta receptor agonist activity
ES2273599B1 (es) 2005-10-14 2008-06-01 Universidad De Barcelona Compuestos para el tratamiento de la fibrilacion auricular.
US7615556B2 (en) * 2006-01-27 2009-11-10 Bristol-Myers Squibb Company Piperazinyl derivatives as modulators of chemokine receptor activity
US20110064671A1 (en) 2008-03-10 2011-03-17 Cornell University Modulation of blood brain barrier permeability
WO2010008775A1 (en) * 2008-06-23 2010-01-21 Ligand Pharmaceuticals Inc. Aminopyridopyrazinone derivatives for treating neurodegenerative diseases
GB201214106D0 (en) * 2012-08-07 2012-09-19 Univ Strathclyde Immunomodulatory compounds
EP3436013A4 (en) 2016-03-31 2019-11-13 Versi Group, LLC DELTA OPIOID AGONIST, MU OPIOID ANTAGONIST COMPOSITIONS AND METHOD FOR TREATING MORBUS PARKINSON
CN106866582A (zh) * 2017-01-10 2017-06-20 广州隽沐生物科技有限公司 一种氟班色林中间体的制备方法
EP3814355A4 (en) 2018-06-26 2022-06-08 Zhejiang Vimgreen Pharmaceuticals, Ltd PYRAZOLOTRIAZOLOPYRIMIDE DERIVATIVES AS A2A RECEPTOR ANTAGONISTS
WO2020227156A1 (en) * 2019-05-03 2020-11-12 Nektar Therapeutics Adenosine 2 receptor antagonists
US20230048888A1 (en) * 2019-12-26 2023-02-16 Zhejiang Vimgreen Pharmaceuticals, Ltd. Use of triazolotriazine derivative in treatment of diseases
MX2023012338A (es) * 2021-04-23 2023-10-30 Chong Kun Dang Pharmaceutical Corp Compuesto como antagonista del receptor de adenosina a2a y composicion farmaceutica que comprende al mismo.

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1264901B1 (it) 1993-06-29 1996-10-17 Schering Plough S P A Analoghi eterociclici di 1,2,4-triazolo(15-c)pirimidine ad attivita' antagonista per il recettore a2 dell'adenosina
AU7237294A (en) * 1993-07-27 1995-02-28 Kyowa Hakko Kogyo Co. Ltd. Remedy for parkinson's disease
IT1277392B1 (it) 1995-07-28 1997-11-10 Schering Plough S P A Analoghi eterociclici di 1,2,4-triazolo(1,5-c]pirimidine ad attivita' antagonista per il recettore a2a dell'adenosina
JP4195729B2 (ja) * 1997-03-24 2008-12-10 協和醗酵工業株式会社 ［１，２，４］トリアゾロ［１，５−ｃ］ピリミジン誘導体
IT1291372B1 (it) 1997-05-21 1999-01-07 Schering Plough S P A Uso di analoghi eterociclici di 1,2,4-triazolo (1,5-c) pirimidine per la preparazione di medicamenti utili per il trattamento delle malattie
WO1999043678A1 (en) 1998-02-24 1999-09-02 Kyowa Hakko Kogyo Co., Ltd. Remedies/preventives for parkinson's disease
BR9914040A (pt) * 1998-09-22 2002-01-15 Kyowa Hakko Kogyo Kk Derivados de [1,2,4]triazolo[1,5-c]pirimidina e seu uso, medicamento, antagonista, agente para prevenir ou tratar doenças, bem como processo para prevenção ou tratamento de distúrbios
US6355653B1 (en) 1999-09-06 2002-03-12 Hoffmann-La Roche Inc. Amino-triazolopyridine derivatives
JP2002037787A (ja) * 2000-05-16 2002-02-06 Kyowa Hakko Kogyo Co Ltd ［１，２，４］トリアゾロ［１，５−ｃ］ピリミジン誘導体の製造法
JP4574112B2 (ja) 2000-05-26 2010-11-04 シェーリング コーポレイション アデノシンａ２ａレセプターアンタゴニスト
JP4545437B2 (ja) 2001-10-15 2010-09-15 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のイミダゾ（４，３−ｅ）−１，２，４−トリアゾロ（１，５−ｃ）ピリミジン
MXPA04005158A (es) * 2001-11-30 2004-08-11 Schering Corp Antagonistas receptores de adenosina a2a biciclica de (1.2.4]- triazol.

Also Published As

Publication number Publication date
KR20050044600A (ko) 2005-05-12
US6875772B2 (en) 2005-04-05
JP4429724B2 (ja) 2010-03-10
HUP0402324A2 (hu) 2005-02-28
HK1064097A1 (en) 2005-01-21
US20030191130A1 (en) 2003-10-09
DE60219196D1 (de) 2007-05-10
TW200300689A (en) 2003-06-16
JP2005511697A (ja) 2005-04-28
ES2283625T3 (es) 2007-11-01
AR037681A1 (es) 2004-12-01
WO2003048163A1 (en) 2003-06-12
EP1453836B1 (en) 2007-03-28
HUP0402324A3 (en) 2008-09-29
CA2468658A1 (en) 2003-06-12
ATE358130T1 (de) 2007-04-15
ZA200404168B (en) 2005-09-02
DE60219196T2 (de) 2008-01-03
JP2010018634A (ja) 2010-01-28
PE20030653A1 (es) 2003-08-04
IL161573A0 (en) 2004-09-27
MXPA04005158A (es) 2004-08-11
US7078408B2 (en) 2006-07-18
AU2002352933A1 (en) 2003-06-17
EP1453836A1 (en) 2004-09-08
CN1688581A (zh) 2005-10-26
US20050113380A1 (en) 2005-05-26

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Effective date: 20131126