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 & Dohme LLC
Original Assignee
Schering Corp
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
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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)
  • Psychology (AREA)
  • Pain & Pain Management (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
TW200300686A (en) 2001-11-30 2003-06-16 Schering Corp Adenosine A2a receptor antagonists
CA2468658C (en) * 2001-11-30 2009-04-14 Schering Corporation [1,2,4]-triazole bicyclic adenosine a2a receptor antagonists
CN101492383A (zh) * 2002-03-12 2009-07-29 惠氏公司 制备手性1,4-二取代哌嗪的方法
AU2003272886A1 (en) * 2002-09-24 2004-04-19 Kyowa Hakko Kogyo Co., Ltd. (1,2,4)-TRIAZOLO(1,5-c)PYRIMIDINE DERIVATIVE
MXPA05006790A (es) 2002-12-19 2005-09-08 Schering Corp Usos de antagonistas del receptor adenosina a2a.
WO2004092170A2 (en) 2003-04-09 2004-10-28 Biogen Idec Ma Inc. Triazolotriazines and pyrazolotriazines useful as a2a adenosine receptor antagon ists
EP1633756B1 (en) 2003-04-09 2008-12-24 Biogen Idec MA Inc. A2a adenosine receptor antagonists
EP1615931A1 (en) 2003-04-09 2006-01-18 Biogen Idec MA Inc. Triazolopyrazines 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
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
JPWO2006132275A1 (ja) 2005-06-07 2009-01-08 協和醗酵工業株式会社 運動障害の予防および／または治療剤
EP1896415A1 (en) * 2005-06-08 2008-03-12 NeuroSearch A/S Novel n-phenyl-piperidine derivatives and their use as monoamine neurotransmitter re-uptake inhibitors
TW200803856A (en) 2005-09-02 2008-01-16 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
JP7175034B2 (ja) * 2018-06-26 2022-11-18 チョーチヤン ビムグリーン ファーマシューティカルズ、リミテッド Ａ２ａ受容体拮抗薬として用いられるトリアゾロトリアジン誘導体
US12325708B2 (en) 2019-05-03 2025-06-10 Nektar Therapeutics Adenosine 2 receptor antagonists
EP4083044A4 (en) * 2019-12-26 2024-03-27 Zhejiang Vimgreen Pharmaceuticals, Ltd USE OF TRIAZOLOTRIAZINE DERIVATIVES TO TREAT DISEASES
EP4326724A4 (en) * 2021-04-23 2025-03-26 Chong Kun Dang Pharmaceutical Corp. COMPOUND CONSTITUTING AN ANTAGONIST OF THE ADENOSINE A2A RECEPTOR AND PHARMACEUTICAL COMPOSITION COMPRISING SAME

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
US5565460A (en) * 1993-07-27 1996-10-15 Kyowa Hakko Koygo Co., Ltd. Therapeutic purine agents 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
WO1998042711A1 (en) * 1997-03-24 1998-10-01 Kyowa Hakko Kogyo Co., Ltd. [1,2,4]TRIAZOLO[1,5-c]PYRIMIDINE DERIVATIVES
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
AU2639299A (en) 1998-02-24 1999-09-15 Kyowa Hakko Kogyo Co. Ltd. Remedies/preventives for parkinson's disease
KR20010087361A (ko) * 1998-09-22 2001-09-15 히라타 다다시 [1,2,4]트리아졸로[1,5-ｃ]피리미딘 유도체
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
PT1283839E (pt) 2000-05-26 2005-08-31 Schering Corp Antagonistas do receptor a2a da adenosina
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
CA2468658C (en) * 2001-11-30 2009-04-14 Schering Corporation [1,2,4]-triazole bicyclic adenosine a2a receptor antagonists

Also Published As

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

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Effective date: 20131126