CA2468681C - Adenosine a2a receptor antagonists - Google Patents

Adenosine a2a receptor antagonists Download PDF

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Publication number
CA2468681C
CA2468681C CA2468681A CA2468681A CA2468681C CA 2468681 C CA2468681 C CA 2468681C CA 2468681 A CA2468681 A CA 2468681A CA 2468681 A CA2468681 A CA 2468681A CA 2468681 C CA2468681 C CA 2468681C
Authority
CA
Canada
Prior art keywords
alkyl
alkoxy
group
mmol
aryl
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
CA2468681A
Other languages
English (en)
French (fr)
Other versions
CA2468681A1 (en
Inventor
Julius J. Matasi
John P. Caldwell
Deen Tulshian
Lisa S. Silverman
Bernard R. Neustadt
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
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 Schering Corp filed Critical Schering Corp
Publication of CA2468681A1 publication Critical patent/CA2468681A1/en
Application granted granted Critical
Publication of CA2468681C publication Critical patent/CA2468681C/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
    • 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
    • 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
    • A61P25/08—Antiepileptics; Anticonvulsants
    • 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
    • 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

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Neurosurgery (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Biomedical Technology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Neurology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Psychiatry (AREA)
  • Pain & Pain Management (AREA)
  • Vascular Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Psychology (AREA)
  • Hospice & Palliative Care (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
CA2468681A 2001-11-30 2002-11-26 Adenosine a2a receptor antagonists Expired - Fee Related CA2468681C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US33429301P 2001-11-30 2001-11-30
US60/334,293 2001-11-30
PCT/US2002/038134 WO2003048164A2 (en) 2001-11-30 2002-11-26 Adenosine a2a receptor antagonists

Publications (2)

Publication Number Publication Date
CA2468681A1 CA2468681A1 (en) 2003-06-12
CA2468681C true CA2468681C (en) 2011-01-25

Family

ID=23306533

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2468681A Expired - Fee Related CA2468681C (en) 2001-11-30 2002-11-26 Adenosine a2a receptor antagonists

Country Status (18)

Country Link
US (1) US7041666B2 (enExample)
EP (1) EP1453835B1 (enExample)
JP (2) JP4284181B2 (enExample)
KR (1) KR20050044607A (enExample)
CN (1) CN1596258A (enExample)
AR (1) AR038366A1 (enExample)
AT (1) ATE317844T1 (enExample)
AU (1) AU2002346572A1 (enExample)
CA (1) CA2468681C (enExample)
DE (1) DE60209251T2 (enExample)
ES (1) ES2258164T3 (enExample)
HU (1) HUP0402270A3 (enExample)
IL (1) IL161572A0 (enExample)
MX (1) MXPA04005156A (enExample)
PE (1) PE20030739A1 (enExample)
TW (1) TW200300686A (enExample)
WO (1) WO2003048164A2 (enExample)
ZA (1) ZA200404160B (enExample)

Families Citing this family (30)

* Cited by examiner, † Cited by third party
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EP1544200A1 (en) * 2002-09-24 2005-06-22 Kyowa Hakko Kogyo Co., Ltd. 1,2,4 -TRIAZOLO 1,5-c PYRIMIDINE DERIVATIVE
US20060106040A1 (en) 2002-12-19 2006-05-18 Michael Grzelak Adenosine A2a receptor antagonists for the treatment of extra-pyramidal syndrome and other movement disorders
CN101310724A (zh) 2002-12-19 2008-11-26 先灵公司 腺苷A2a受体拮抗剂的应用
US20070010522A1 (en) * 2003-04-09 2007-01-11 Chi Vu Triazolo[1,5-c]pyrimidines and pyrazolo[1,5-c]pyrimidines useful as a2a adenosine receptor antagonists
CA2541989C (en) * 2003-10-24 2013-10-01 Exelixis, Inc. P70s6 kinase modulators and method of use
AR050926A1 (es) * 2004-09-03 2006-12-06 Astrazeneca Ab Derivados de benzamida como inhibidores de la histonadesacetilasa(hdac)
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
ES2273599B1 (es) 2005-10-14 2008-06-01 Universidad De Barcelona Compuestos para el tratamiento de la fibrilacion auricular.
US8835631B2 (en) * 2007-05-24 2014-09-16 Mitsubishi Tanabe Pharma Corporation Therapeutic agent for cerebral infarction
CA2690748A1 (en) * 2007-06-25 2008-12-31 Neurogen Corporation Piperazinyl oxoalkyl tetrahydro-beta-carbolines and related analogues
US20100093764A1 (en) * 2008-10-13 2010-04-15 Devraj Chakravarty AMINES AND SULFOXIDES OF THIENO[2,3-d]PYRIMIDINE AND THEIR USE AS ADENOSINE A2a RECEPTOR ANTAGONISTS
US20100093756A1 (en) * 2008-10-13 2010-04-15 Berbay J Kent HETEROARYL SUBSTITUTED THIENO[2,3-d]PYRIMIDINE AND THEIR USE AS ADENOSINE A2a RECEPTOR ANTAGONISTS
WO2010061696A1 (ja) 2008-11-25 2010-06-03 日産自動車株式会社 導電部材及びこれを用いた固体高分子形燃料電池
EP2424840B1 (en) * 2009-04-27 2014-08-06 Boehringer Ingelheim International GmbH Cxcr3 receptor antagonists
WO2011084985A1 (en) 2010-01-07 2011-07-14 Boehringer Ingelheim International Gmbh Cxcr3 receptor antagonists
JP5843869B2 (ja) * 2010-09-24 2016-01-13 アドヴィナス・セラピューティックス・リミテッド アデノシン受容体拮抗薬としての縮合三環化合物
WO2012127472A1 (en) * 2011-03-22 2012-09-27 Mapi Pharma Ltd. Process and intermediates for the preparation of preladenant and related compounds
JP7065113B2 (ja) * 2017-04-07 2022-05-11 南京明徳新薬研発有限公司 Ａ２Ａ受容体阻害剤としての［１，２，４］トリアゾロ［１，５－ｃ］ピリミジン誘導体
CA3092470A1 (en) * 2018-02-27 2019-09-06 Incyte Corporation Imidazopyrimidines and triazolopyrimidines as a2a / a2b inhibitors
CN112105617B (zh) * 2018-04-28 2022-04-05 南京明德新药研发有限公司 一种三唑并嘧啶类化合物的晶型、盐型及其制备方法
JP7391046B2 (ja) * 2018-05-18 2023-12-04 インサイト・コーポレイション Ａ２ａ／ａ２ｂ阻害剤としての縮合ピリミジン誘導体
JP7490631B2 (ja) 2018-07-05 2024-05-27 インサイト・コーポレイション Ａ２ａ／ａ２ｂ阻害剤としての縮合ピラジン誘導体
TWI820209B (zh) 2018-09-12 2023-11-01 大陸商迪哲（江蘇）醫藥股份有限公司 三唑并－嘧啶化合物及其用途
WO2020106560A1 (en) * 2018-11-20 2020-05-28 Merck Sharp & Dohme Corp. Substituted amino triazolopyrimidine and amino triazolopyrazine adenosine receptor antagonists, pharmaceutical compositions and their use
US12466831B2 (en) * 2018-11-20 2025-11-11 Merck Sharp & Dohme Llc Substituted amino triazolopyrimidine and amino triazolopyrazine adenosine receptor antagonists, pharmaceutical compositions and their use
AU2019388872A1 (en) 2018-11-30 2021-05-27 Merck Sharp & Dohme Llc 7-, 8-, and 10-substituted amino triazolo quinazoline derivatives as adenosine receptor antagonists, pharmaceutical compositions and their use
EA202191498A1 (ru) 2018-11-30 2021-08-20 Мерк Шарп энд Доум Корп. 9-замещенные производные аминотриазолохиназолина в качестве антагонистов аденозиновых рецепторов, фармацевтические композиции и их применение
BR112021011948A2 (pt) 2018-12-20 2021-09-08 Incyte Corporation Compostos de imidazopiridazina e imidazopiridina e usos dos mesmos
WO2020128036A1 (en) * 2018-12-21 2020-06-25 Ryvu Therapeutics S.A. Modulators of the adenosine a2a receptor
TWI829857B (zh) 2019-01-29 2024-01-21 美商英塞特公司 作為a2a / a2b抑制劑之吡唑并吡啶及三唑并吡啶

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU622330B2 (en) 1989-06-23 1992-04-02 Takeda Chemical Industries Ltd. Condensed heterocyclic compounds having a nitrogen atom in the bridgehead for use as fungicides
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
DE69428977T2 (de) 1993-07-27 2002-07-11 Kyowa Hakko Kogyo Co., Ltd. Arzneimittel gegen Parkinsonsche Krankheit
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
AU743910B2 (en) 1997-03-24 2002-02-07 Kyowa Hakko Kirin 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
CN1328560A (zh) 1998-09-22 2001-12-26 协和发酵工业株式会社 [1,2,4]三唑并[1,5－c]嘧啶衍生物
DE60110219T2 (de) 2000-05-26 2006-03-09 Schering Corp. Adenosin a2a rezeptor antagonisten
WO2002079204A1 (en) * 2001-03-28 2002-10-10 Kyowa Hakko Kogyo Co., Ltd. 8-thiazolyl[1,2,4]triazolo[1,5-c]pyrimidine derivative
WO2003048163A1 (en) 2001-11-30 2003-06-12 Schering Corporation [1,2,4]-TRIAZOLE BICYCLIC ADENOSINE A2a RECEPTOR ANTAGONISTS

Also Published As

Publication number Publication date
EP1453835A2 (en) 2004-09-08
WO2003048164A2 (en) 2003-06-12
DE60209251T2 (de) 2006-11-09
ES2258164T3 (es) 2006-08-16
TW200300686A (en) 2003-06-16
KR20050044607A (ko) 2005-05-12
HUP0402270A3 (en) 2008-09-29
IL161572A0 (en) 2004-09-27
DE60209251D1 (de) 2006-04-20
CA2468681A1 (en) 2003-06-12
HK1064100A1 (en) 2005-01-21
CN1596258A (zh) 2005-03-16
MXPA04005156A (es) 2004-08-11
PE20030739A1 (es) 2003-08-28
JP2005511698A (ja) 2005-04-28
HUP0402270A2 (hu) 2005-02-28
JP4284181B2 (ja) 2009-06-24
ATE317844T1 (de) 2006-03-15
US7041666B2 (en) 2006-05-09
WO2003048164A3 (en) 2003-10-16
EP1453835B1 (en) 2006-02-15
JP2008303217A (ja) 2008-12-18
AU2002346572A1 (en) 2003-06-17
AR038366A1 (es) 2005-01-12
US20030212080A1 (en) 2003-11-13
ZA200404160B (en) 2005-04-08

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Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed

Effective date: 20131126