CA2410237C - Adenosine a2a receptor antagonists - Google Patents

Adenosine a2a receptor antagonists Download PDF

Info

Publication number
CA2410237C
CA2410237C CA002410237A CA2410237A CA2410237C CA 2410237 C CA2410237 C CA 2410237C CA 002410237 A CA002410237 A CA 002410237A CA 2410237 A CA2410237 A CA 2410237A CA 2410237 C CA2410237 C CA 2410237C
Authority
CA
Canada
Prior art keywords
alkyl
alkoxy
compound
formula
pharmaceutically acceptable
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 - Lifetime
Application number
CA002410237A
Other languages
English (en)
French (fr)
Other versions
CA2410237A1 (en
Inventor
Bernard R. Neustadt
Neil A. Lindo
William J. Greenlee
Deen Tulshian
Lisa S. Silverman
Yan Xia
Craig D. Boyle
Samuel Chackalamannil
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 CA2410237A1 publication Critical patent/CA2410237A1/en
Application granted granted Critical
Publication of CA2410237C publication Critical patent/CA2410237C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D487/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/12Heterocyclic 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
    • C07D487/14Ortho-condensed systems
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/08Antiepileptics; Anticonvulsants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/14Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16Anti-Parkinson drugs
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/24Antidepressants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/28Drugs 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Pain & Pain Management (AREA)
  • Psychiatry (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
CA002410237A 2000-05-26 2001-05-24 Adenosine a2a receptor antagonists Expired - Lifetime CA2410237C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US20714300P 2000-05-26 2000-05-26
US60/207,143 2000-05-26
PCT/US2001/016954 WO2001092264A1 (en) 2000-05-26 2001-05-24 Adenosine a2a receptor antagonists

Publications (2)

Publication Number Publication Date
CA2410237A1 CA2410237A1 (en) 2001-12-06
CA2410237C true CA2410237C (en) 2008-01-08

Family

ID=22769372

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002410237A Expired - Lifetime CA2410237C (en) 2000-05-26 2001-05-24 Adenosine a2a receptor antagonists

Country Status (31)

Country Link
US (4) US6630475B2 (enExample)
EP (1) EP1283839B1 (enExample)
JP (3) JP4574112B2 (enExample)
KR (1) KR100520907B1 (enExample)
CN (2) CN100384847C (enExample)
AR (1) AR028621A1 (enExample)
AT (1) ATE293627T1 (enExample)
AU (2) AU6808901A (enExample)
BR (1) BRPI0111015B8 (enExample)
CA (1) CA2410237C (enExample)
CZ (1) CZ303790B6 (enExample)
DE (1) DE60110219T2 (enExample)
DK (1) DK1283839T3 (enExample)
EC (1) ECSP024364A (enExample)
ES (1) ES2237576T3 (enExample)
HK (1) HK1049007B (enExample)
HU (1) HU230420B1 (enExample)
IL (3) IL152726A0 (enExample)
MX (1) MXPA02011625A (enExample)
MY (1) MY132006A (enExample)
NO (1) NO325008B1 (enExample)
NZ (1) NZ522326A (enExample)
PE (1) PE20020062A1 (enExample)
PL (1) PL218764B1 (enExample)
PT (1) PT1283839E (enExample)
RU (1) RU2315053C2 (enExample)
SI (1) SI1283839T1 (enExample)
SK (1) SK287748B6 (enExample)
TW (1) TWI288137B (enExample)
WO (1) WO2001092264A1 (enExample)
ZA (1) ZA200208898B (enExample)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014071512A1 (en) * 2012-11-06 2014-05-15 Universite Laval Combination therapy and methods for the treatment of respiratory diseases

Families Citing this family (87)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
CA2459304A1 (en) * 2001-09-13 2003-03-20 Schering Corporation Combination of an adenosine a2a receptor antagonist and an antidepressant or anxiolytic
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
FR2832405B1 (fr) * 2001-11-19 2004-12-10 Sanofi Synthelabo Tetrahydropyridyl-alkyl-heterocycles azotes, procede pour leur preparation et compositions pharmaceutiques les contenant
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
KR20050044593A (ko) * 2001-11-30 2005-05-12 쉐링 코포레이션 아데노신 A2a 수용체 길항제
KR20150080013A (ko) 2002-01-28 2015-07-08 교와 핫꼬 기린 가부시키가이샤 운동성 질환에 걸린 환자의 치료용 조성물
US7064204B2 (en) * 2002-05-30 2006-06-20 King Pharmacueticals Reserch And Development, Inc. Pharmaceutically active compounds having a tricyclic pyrazolotriazolopyrimidine ring structure and methods of use
WO2005044245A1 (en) * 2002-12-19 2005-05-19 Schering Corporation USES OF ADENOSINE A2a RECEPTOR ANTAGONISTS
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
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
MXPA05011366A (es) * 2003-04-23 2005-11-28 Schering Corp Antagonistas del receptor a2a de 2-alquinil- y 2-alquenil-pirazolo-[4,3-e]-1,2,4-triazolo-[1,5-c]-pirimidina adenosina.
KR20060037252A (ko) * 2003-06-10 2006-05-03 교와 핫꼬 고교 가부시끼가이샤 불안 장애의 치료 방법
WO2004111004A1 (en) * 2003-06-12 2004-12-23 Novo Nordisk A/S Substituted piperazine carbamates for use as inhibitors of hormone sensitive lipase
JP4800216B2 (ja) * 2003-10-24 2011-10-26 エグゼリクシス, インコーポレイテッド p70S6キナーゼモジュレーターおよび使用方法
WO2005044819A1 (en) * 2003-10-28 2005-05-19 Schering Corporation Process for preparing substituted 5-amino-pyrazolo-[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidines
ATE377599T1 (de) 2003-12-01 2007-11-15 Schering Corp Verfahren zur herstellung von substituierten 5- aminopyrazolo(4,3-e)-1,2,4-triazolo(1,5- c)pyrimidinen
ATE516011T1 (de) * 2003-12-19 2011-07-15 Schering Corp Pharmazeutische zusammensetzungen eines a2a rezeptorantagonisten
DE602005020127D1 (de) 2004-04-21 2010-05-06 Schering Corp Pyrazoloä4,3-eü-1,2,4-triazoloä1,5-cüpyrimidine als antagonisten des adenosin-a2a-rezeptors
EP2258372B8 (en) 2005-06-07 2012-12-19 Kyowa Hakko Kirin Co., Ltd. A2A antagonists for use in the treatment of motor disorders
JP2009508871A (ja) * 2005-09-19 2009-03-05 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2−ヘテロアリール−ピラゾロ−[4,3−e]−1,2,4−トリアゾロ−[1,5−c]−ピリミジン
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
ES2273599B1 (es) 2005-10-14 2008-06-01 Universidad De Barcelona Compuestos para el tratamiento de la fibrilacion auricular.
JP5539717B2 (ja) * 2006-07-14 2014-07-02 塩野義製薬株式会社 オキシム化合物およびその使用
TW200840566A (en) * 2006-12-22 2008-10-16 Esteve Labor Dr Heterocyclyl-substituted-ethylamino-phenyl derivatives, their preparation and use as medicaments
US7723343B2 (en) * 2007-03-30 2010-05-25 King Pharmaceuticals Research And Development, Inc. Adenosine A2A receptor antagonists
US8669260B2 (en) * 2008-02-29 2014-03-11 Albert Einstein College Of Medicine Of Yeshiva University Ketoconazole-derivative antagonist of human pregnane X receptor and uses thereof
WO2009111449A1 (en) 2008-03-04 2009-09-11 Schering Corporation 1,2,4-triazolo[4,3-c]pyrimidin-3-one and pyrazolo [4,3-e] -1,2,4-triazolo [4,3-c] pyrimidin-3-one compounds for use as adenosine a2a receptor antagonists
US20110064671A1 (en) 2008-03-10 2011-03-17 Cornell University Modulation of blood brain barrier permeability
TWI473614B (zh) * 2008-05-29 2015-02-21 Kyowa Hakko Kirin Co Ltd Anti-analgesic inhibitors
MX2011000788A (es) * 2008-07-23 2011-03-21 Kyowa Hakko Kirin Co Ltd Agente terapeutico para migraña.
US20100093702A1 (en) * 2008-10-13 2010-04-15 Barbay J Kent METHYLENE AMINES OF THIENO[2,3-d]PYRIMIDINE AND THEIR USE AS ADENOSINE A2a RECEPTOR ANTAGONISTS
EP2379556A1 (en) 2008-12-30 2011-10-26 ArQule, Inc. Substituted 1h-pyrazolo[3,4-d]pyrimidine-6-amine compounds
EP2389175A1 (en) 2009-01-20 2011-11-30 Schering Corporation Methods of alleviating or treating signs and/or symptoms associated with moderate to severe parkinson's disease
WO2010084160A1 (en) 2009-01-21 2010-07-29 Oryzon Genomics S.A. Phenylcyclopropylamine derivatives and their medical use
EP2405917B1 (en) 2009-03-13 2014-04-23 Advinus Therapeutics Private Limited Substituted fused pyrimidine compounds
WO2010114894A1 (en) 2009-03-31 2010-10-07 Arqule, Inc. Substituted heterocyclic compounds
WO2010147941A1 (en) 2009-06-15 2010-12-23 Marvell World Trade Ltd. System and methods for gamut bounded saturation adaptive color enhancement
WO2011017299A2 (en) 2009-08-07 2011-02-10 Schering Corporation PROCESS FOR PREPARING A 2-ALKYNYL SUBSTITUTED 5-AMINO-PYRAZOLO-[4,3-e]-1,2,4-TRIAZOLO[1,5-c]PYRIMIDINE
KR101736218B1 (ko) 2009-09-25 2017-05-16 오리존 지노믹스 에스.에이. 라이신 특이적 디메틸라아제-1 억제제 및 이의 용도
EP2486002B1 (en) 2009-10-09 2019-03-27 Oryzon Genomics, S.A. Substituted heteroaryl- and aryl- cyclopropylamine acetamides and their use
WO2011101861A1 (en) 2010-01-29 2011-08-25 Msn Laboratories Limited Process for preparation of dpp-iv inhibitors
US9186337B2 (en) 2010-02-24 2015-11-17 Oryzon Genomics S.A. Lysine demethylase inhibitors for diseases and disorders associated with Hepadnaviridae
WO2011106574A2 (en) 2010-02-24 2011-09-01 Oryzon Genomics, S.A. Inhibitors for antiviral use
ES2607081T3 (es) 2010-04-19 2017-03-29 Oryzon Genomics, S.A. Inhibidores de desmetilasa específica de lisina-1 y su uso
US9006449B2 (en) 2010-07-29 2015-04-14 Oryzon Genomics, S.A. Cyclopropylamine derivatives useful as LSD1 inhibitors
LT2598482T (lt) 2010-07-29 2018-07-10 Oryzon Genomics, S.A. Demetilazės lsd1 inhibitoriai arilciklopropilamino pagrindu ir jų medicininis panaudojimas
US9006177B2 (en) * 2010-09-24 2015-04-14 Advinus Therapeutics Limited Fused tricyclic compounds as adenosine receptor antagonist
US9061966B2 (en) 2010-10-08 2015-06-23 Oryzon Genomics S.A. Cyclopropylamine inhibitors of oxidases
WO2012072713A2 (en) 2010-11-30 2012-06-07 Oryzon Genomics, S.A. Lysine demethylase inhibitors for diseases and disorders associated with flaviviridae
WO2012107498A1 (en) 2011-02-08 2012-08-16 Oryzon Genomics S.A. Lysine demethylase inhibitors for myeloproliferative disorders
WO2012129381A1 (en) * 2011-03-22 2012-09-27 Concert Pharmaceuticals Inc. Deuterated preladenant
WO2012127472A1 (en) * 2011-03-22 2012-09-27 Mapi Pharma Ltd. Process and intermediates for the preparation of preladenant and related compounds
WO2013024474A1 (en) * 2011-08-18 2013-02-21 Mapi Phrarma Ltd. Polymorphs of preladenant
SI2776394T1 (sl) 2011-10-20 2019-05-31 Oryzon Genomics, S.A. Spojine (hetero)aril ciklopropilamina kot inhibitorji LSD1
EP3736265A1 (en) 2011-10-20 2020-11-11 Oryzon Genomics, S.A. (hetero)aryl cyclopropylamine compounds as lsd1 inhibitors
WO2014101120A1 (en) * 2012-12-28 2014-07-03 Merck Sharp & Dohme Corp. Heterobicyclo-substituted-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine compounds with a2a antagonist properties
WO2016081290A1 (en) 2014-11-18 2016-05-26 Merck Sharp & Dohme Corp. Aminopyrazine compounds with a2a antagonist properties
WO2016126570A1 (en) 2015-02-06 2016-08-11 Merck Sharp & Dohme Corp. Aminoquinazoline compounds as a2a antagonist
EP3307067B1 (en) 2015-06-11 2022-11-02 Merck Sharp & Dohme LLC Aminopyrazine compounds with a2a antagonist properties
WO2017008205A1 (en) 2015-07-10 2017-01-19 Merck Sharp & Dohme Corp. Substituted aminoquinazoline compounds as a2a antagonist
US9687475B1 (en) 2016-03-24 2017-06-27 Ezra Pharma Llc Extended release pharmaceutical formulations with controlled impurity levels
US9675585B1 (en) 2016-03-24 2017-06-13 Ezra Pharma Extended release pharmaceutical formulations
CN110678472B (zh) * 2017-03-30 2023-01-24 伊忒欧斯比利时股份公司 作为a2a抑制剂的2-氧代噻唑衍生物和用于治疗癌症的化合物
WO2018178338A1 (en) * 2017-03-30 2018-10-04 Iteos Therapeutics 2-oxo-thiazole derivatives as a2a inhibitors and compounds for use in the treatment of cancers
US11498923B2 (en) 2017-12-13 2022-11-15 Merck Sharp & Dohme Llc Substituted imidazo[1,2-c]quinazolines as A2A antagonists
ES2928238T3 (es) 2018-01-04 2022-11-16 Impetis Biosciences Ltd Compuestos tricíclicos, composiciones y aplicaciones medicinales de los mismos
WO2019168847A1 (en) 2018-02-27 2019-09-06 Incyte Corporation Imidazopyrimidines and triazolopyrimidines as a2a / a2b inhibitors
CN108276345A (zh) * 2018-03-22 2018-07-13 重庆奥舍生物化工有限公司 一种药物中间体嘧啶-5-甲醛的制备方法
CA3095839A1 (en) * 2018-04-08 2019-10-17 Beigene, Ltd. Pyrazolotriazolopyrimidine derivatives as a2a receptor antagonist
US11168089B2 (en) 2018-05-18 2021-11-09 Incyte Corporation Fused pyrimidine derivatives as A2A / A2B inhibitors
CN108864114B (zh) 2018-06-04 2020-11-06 应世生物科技(南京)有限公司 选择性a2a受体拮抗剂
JOP20200342A1 (ar) 2018-07-05 2020-12-30 Incyte Corp مشتقات بيرازين مدمجة كمثبطات a2a/a2b
CN110742893B (zh) * 2018-07-23 2024-04-05 百济神州(北京)生物科技有限公司 A2a受体拮抗剂治疗癌症的方法
JOP20210117A1 (ar) 2018-11-30 2023-01-30 Merck Sharp & Dohme مشتقات أمينو ترايازولو كوينازولين بها استبدال في الموضع-9 كمضادات مستقبل أدينوزين، تركيبات صيدلانية واستخدامها
CR20210336A (es) 2018-12-20 2021-12-06 Incyte Corp Compuestos de imidazopiridazina e imidazopiridina como inhibidores de quinasa-2 de tipo receptor de activina
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
WO2020227156A1 (en) * 2019-05-03 2020-11-12 Nektar Therapeutics Adenosine 2 receptor antagonists
DE102019116986A1 (de) 2019-06-24 2020-12-24 Helmholtz-Zentrum Dresden-Rossendorf E. V. Deuterierte 7-(3-(4-(2-([18F]Fluor)ethoxy)phenyl)propyl)-2-(furan-2-yl)-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amin-Derivate
EP3999513A4 (en) * 2019-07-17 2022-12-21 Teon Therapeutics, Inc. ADENOSIN A2A RECEPTOR ANTAGONISTS AND USES THEREOF
CN112625050B (zh) 2019-07-30 2021-10-01 杭州阿诺生物医药科技有限公司 一种a2a和/或a2b受体抑制剂的制备方法
CN112608316B (zh) 2019-07-30 2022-10-21 厦门宝太生物科技股份有限公司 一种吡唑并三嗪类腺苷受体拮抗剂
CN111072675A (zh) * 2019-12-12 2020-04-28 广东东阳光药业有限公司 含氮稠合三环衍生物及其用途
CN113773327B (zh) * 2021-09-13 2022-07-15 八叶草健康产业研究院(厦门)有限公司 一种吡唑并嘧啶并三唑环类化合物的制备方法
CN118812544A (zh) * 2024-06-19 2024-10-22 厦门大学 一种腺苷a2ar靶向小分子化合物、核素标记探针及其制备方法、应用和药物组合物
CN118812539B (zh) * 2024-06-19 2025-11-28 苏州大学 一种5-氨基三唑并嘧啶衍生物及其制备方法

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0217748B1 (en) 1985-09-30 1991-02-06 Ciba-Geigy Ag 2-Substituted-e-fused-[1,2,4,]triazolo-[1,5-c]pyrimidines pharmaceutical compositions and uses thereof
SU1739850A3 (ru) * 1987-08-31 1992-06-07 Такеда Кемикал Индастриз, Лтд (Фирма) Способ получени конденсированных производных пиразоло[3,4- @ ]пиримидина
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
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
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
KR20050044593A (ko) * 2001-11-30 2005-05-12 쉐링 코포레이션 아데노신 A2a 수용체 길항제
WO2005044245A1 (en) * 2002-12-19 2005-05-19 Schering Corporation USES OF ADENOSINE A2a RECEPTOR ANTAGONISTS
WO2005044819A1 (en) * 2003-10-28 2005-05-19 Schering Corporation Process for preparing substituted 5-amino-pyrazolo-[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidines
ATE377599T1 (de) * 2003-12-01 2007-11-15 Schering Corp Verfahren zur herstellung von substituierten 5- aminopyrazolo(4,3-e)-1,2,4-triazolo(1,5- c)pyrimidinen
DE602005020127D1 (de) * 2004-04-21 2010-05-06 Schering Corp Pyrazoloä4,3-eü-1,2,4-triazoloä1,5-cüpyrimidine als antagonisten des adenosin-a2a-rezeptors
JP2009508871A (ja) * 2005-09-19 2009-03-05 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2−ヘテロアリール−ピラゾロ−[4,3−e]−1,2,4−トリアゾロ−[1,5−c]−ピリミジン

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014071512A1 (en) * 2012-11-06 2014-05-15 Universite Laval Combination therapy and methods for the treatment of respiratory diseases

Also Published As

Publication number Publication date
MY132006A (en) 2007-09-28
JP2003535094A (ja) 2003-11-25
IL152726A0 (en) 2003-06-24
PE20020062A1 (es) 2002-02-02
US7067655B2 (en) 2006-06-27
CA2410237A1 (en) 2001-12-06
US20050026932A1 (en) 2005-02-03
HU230420B1 (hu) 2016-05-30
PT1283839E (pt) 2005-08-31
ECSP024364A (es) 2003-03-31
NO20025651L (no) 2003-01-23
CN1800186A (zh) 2006-07-12
IL220174A0 (en) 2012-07-31
DE60110219D1 (de) 2005-05-25
HK1049007A1 (en) 2003-04-25
KR100520907B1 (ko) 2005-10-11
WO2001092264A1 (en) 2001-12-06
EP1283839A1 (en) 2003-02-19
US6630475B2 (en) 2003-10-07
SK16712002A3 (sk) 2003-08-05
NO325008B1 (no) 2008-01-14
DE60110219T2 (de) 2006-03-09
TWI288137B (en) 2007-10-11
NO20025651D0 (no) 2002-11-25
IL152726A (en) 2012-07-31
NZ522326A (en) 2006-03-31
ES2237576T3 (es) 2005-08-01
BRPI0111015B8 (pt) 2021-05-25
DK1283839T3 (da) 2005-07-25
EP1283839B1 (en) 2005-04-20
US20020099061A1 (en) 2002-07-25
PL218764B1 (pl) 2015-01-30
HUP0600239A2 (en) 2006-07-28
CN1451007A (zh) 2003-10-22
BR0111015A (pt) 2005-01-11
JP2006219497A (ja) 2006-08-24
AU2001268089B2 (en) 2005-04-28
IL220174A (en) 2015-07-30
USRE44205E1 (en) 2013-05-07
CN1247588C (zh) 2006-03-29
SI1283839T1 (enExample) 2005-08-31
CN100384847C (zh) 2008-04-30
PL360472A1 (en) 2004-09-06
ZA200208898B (en) 2004-03-01
JP2007145875A (ja) 2007-06-14
AR028621A1 (es) 2003-05-14
US20040023997A1 (en) 2004-02-05
CZ20023886A3 (cs) 2003-02-12
HK1049007B (en) 2005-09-16
KR20030003746A (ko) 2003-01-10
AU2001268089C1 (en) 2006-04-13
AU6808901A (en) 2001-12-11
SK287748B6 (sk) 2011-08-04
JP4574112B2 (ja) 2010-11-04
BRPI0111015B1 (pt) 2017-11-07
ATE293627T1 (de) 2005-05-15
MXPA02011625A (es) 2003-03-27
US6897216B2 (en) 2005-05-24
RU2315053C2 (ru) 2008-01-20
JP4938348B2 (ja) 2012-05-23
CZ303790B6 (cs) 2013-05-09
HUP0600239A3 (en) 2008-06-30

Similar Documents

Publication Publication Date Title
CA2410237C (en) Adenosine a2a receptor antagonists
AU2001268089A1 (en) Adenosine A2a receptor antagonists
AU2002340184B2 (en) Imidazo (4,3-E)-1,2,4-triazolo(1,5-C) pyrimidines as adenosine A2A receptor antagonists
AU2005236059B2 (en) Pyrazolo-[4,3-e]-1,2,4-triazolo-[1,5-c]-pyrimidine adenosine A2a receptor antagonists
CA2468649C (en) Adenosine a2a receptor antagonists
EP1453835B1 (en) Adenosine a 2a receptor antagonists
EP1453836B1 (en) BICYCLIC [1,2,4] -TRIAZOLE ADENOSINE A2a RECEPTOR ANTAGONISTS
EP1934227B1 (en) 2-HETEROARYL-PYRAZOLO-[4, 3-e]-1, 2, 4-TRIAZOLO-[1,5-c]-PYRIMIDINE AS ADENOSINE A2a RECEPTOR ANTAGONISTS
HK1064097B (en) Bicyclic [1,2,4] -triazole adenosine a2a receptor antagonists
HK1064100B (en) Adenosine a 2a receptor antagonists
HK1108882A1 (en) Pyrazolo[1,5-a]pyrimidine adenosine a2a receptor antagonists
HK1108882B (en) Pyrazolo[1,5-a]pyrimidine adenosine a2a receptor antagonists

Legal Events

Date Code Title Description
EEER Examination request
MKEX Expiry

Effective date: 20210525