CN100421663C - 咪唑并（4,3－E）,1,2,4－三唑并（1,5－C）嘧啶类化合物作为腺苷A2a受体拮抗剂 - Google Patents

咪唑并（4,3－E）,1,2,4－三唑并（1,5－C）嘧啶类化合物作为腺苷A2a受体拮抗剂 Download PDF

Info

Publication number
CN100421663C
CN100421663C CNB028203283A CN02820328A CN100421663C CN 100421663 C CN100421663 C CN 100421663C CN B028203283 A CNB028203283 A CN B028203283A CN 02820328 A CN02820328 A CN 02820328A CN 100421663 C CN100421663 C CN 100421663C
Authority
CN
China
Prior art keywords
alkoxyl
alkyl
heteroaryl
chemical compound
formula
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
CNB028203283A
Other languages
English (en)
Chinese (zh)
Other versions
CN1612736A (zh
Inventor
D·图尔施安
L·S·西尔弗曼
J·J·马塔西
E·Y·基谢戈夫
J·P·卡德维尔
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 CN1612736A publication Critical patent/CN1612736A/zh
Application granted granted Critical
Publication of CN100421663C publication Critical patent/CN100421663C/zh
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

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
    • C07D487/12—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

Landscapes

  • 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)
CNB028203283A 2001-10-15 2002-10-11 咪唑并（4,3－E）,1,2,4－三唑并（1,5－C）嘧啶类化合物作为腺苷A2a受体拮抗剂 Expired - Fee Related CN100421663C (zh)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US32956701P 2001-10-15 2001-10-15
US60/329,567 2001-10-15

Publications (2)

Publication Number Publication Date
CN1612736A CN1612736A (zh) 2005-05-04
CN100421663C true CN100421663C (zh) 2008-10-01

Family

ID=23286007

Family Applications (1)

Application Number Title Priority Date Filing Date
CNB028203283A Expired - Fee Related CN100421663C (zh) 2001-10-15 2002-10-11 咪唑并（4,3－E）,1,2,4－三唑并（1,5－C）嘧啶类化合物作为腺苷A2a受体拮抗剂

Country Status (16)

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

Families Citing this family (44)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6875772B2 (en) * 2001-11-30 2005-04-05 Schering Corporation [1,2,4]-Triazole bicyclic adeonsine A2a receptor antagonists
US20040127510A1 (en) * 2002-04-16 2004-07-01 Heintzelman Geoffrey R. Arylindenopyridines and arylindenopyrimidines and related therapeutic and prophylactic methods
MXPA05006790A (es) 2002-12-19 2005-09-08 Schering Corp Usos de antagonistas del receptor adenosina a2a.
DK1622912T3 (da) 2003-04-23 2009-09-07 Schering Corp 2-alkynyl- og 2-alkenyl-pyrazolo-[4,3-E]-1,2,4-triazolo-[1,5-C]-pyrimidinadenosin-A2A-receptorantagonister
CA2528710C (en) * 2003-06-10 2012-04-17 Kyowa Hakko Kogyo Co., Ltd. A method of treating an anxiety disorder
CN100528162C (zh) * 2003-12-19 2009-08-19 先灵公司 药物组合物
EP1745047B1 (en) * 2004-04-21 2010-03-24 Schering Corporation 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
CA2622741A1 (en) * 2005-09-19 2007-03-29 Schering Corporation 2-heteroaryl-pyrazolo-[4, 3-e]-1, 2, 4-triazolo-[1,5-c]-pyrimidine as adenosine a2a receptor antagonists
PE20070521A1 (es) 2005-09-23 2007-07-13 Schering Corp 7-[2-[4-(6-FLUORO-3-METIL-1,2-BENCISOXAZOL-5-IL)-1-PIPERAZINIL]ETIL]-2-(1-PROPINIL)-7H-PIRAZOL-[4,3-E]-[1,2,4]-TRIAZOL-[1,5-C]-PIRIMIDIN-5-AMINA COMO ANTAGONISTA DEL RECEPTOR DE ADENOSINA A2a
ES2273599B1 (es) 2005-10-14 2008-06-01 Universidad De Barcelona Compuestos para el tratamiento de la fibrilacion auricular.
TW200817039A (en) * 2006-10-06 2008-04-16 Dynamis Therapeutics Inc Compositions and methods for skin lightening
JP5486928B2 (ja) * 2007-02-26 2014-05-07 ヴァイティー ファーマシューティカルズ，インコーポレイテッド １１β−ヒドロキシステロイドデヒドロゲナーゼ１のサイクリックウレアおよびカルバメートインヒビター
US7723343B2 (en) 2007-03-30 2010-05-25 King Pharmaceuticals Research And Development, Inc. Adenosine A2A receptor antagonists
CA2697168A1 (en) * 2007-07-26 2009-02-05 Vitae Pharmaceuticals, Inc. Synthesis of inhibitors of 11beta-hydroxysteroid dehydrogenase type 1
AR069207A1 (es) * 2007-11-07 2010-01-06 Vitae Pharmaceuticals Inc Ureas ciclicas como inhibidores de la 11 beta - hidroxi-esteroide deshidrogenasa 1
CA2708303A1 (en) 2007-12-11 2009-06-18 Vitae Pharmaceuticals, Inc. Cyclic urea inhibitors of 11.beta.-hydroxysteroid dehydrogenase 1
TW200934490A (en) * 2008-01-07 2009-08-16 Vitae Pharmaceuticals Inc Lactam inhibitors of 11 &abgr;-hydroxysteroid dehydrogenase 1
JP5490020B2 (ja) 2008-01-24 2014-05-14 ヴァイティー ファーマシューティカルズ，インコーポレイテッド １１β−ヒドロキシステロイドデヒドロゲナーゼ１の環状カルバゼート及びセミカルバジドインヒビター
JP5734666B2 (ja) * 2008-02-11 2015-06-17 ヴァイティー ファーマシューティカルズ，インコーポレイテッド １１β−ヒドロキシステロイドデヒドロゲナーゼ１の１，３−オキサアゼパン−２−オン及び１，３−ジアゼパン−２−オン阻害剤
JP5730021B2 (ja) * 2008-02-15 2015-06-03 ヴァイティー ファーマシューティカルズ，インコーポレイテッド １１β−ヒドロキシステロイドデヒドロゲナーゼ１の阻害剤としてのシクロアルキルラクタム誘導体
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
JP5538356B2 (ja) * 2008-03-18 2014-07-02 ヴァイティー ファーマシューティカルズ，インコーポレイテッド １１β−ヒドロキシステロイドデヒドロゲナーゼ１型の阻害剤
WO2009134384A1 (en) * 2008-05-01 2009-11-05 Vitae Pharmaceuticals, Inc. Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1
TW201004945A (en) 2008-05-01 2010-02-01 Vitae Pharmaceuticals Inc Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1
CA2722427A1 (en) 2008-05-01 2009-11-05 Vitae Pharmaceuticals, Inc. Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1
US8592410B2 (en) 2008-05-01 2013-11-26 Vitae Pharmaceuticals, Inc. Cyclic inhibitors of 11BETA-hydroxysteroid dehydrogenase 1
ES2432150T3 (es) 2008-07-25 2013-12-02 Boehringer Ingelheim International Gmbh Inhibidores cíclicos de la 11 beta-hidroxiesteroide deshidrogenasa 1
US8846668B2 (en) 2008-07-25 2014-09-30 Vitae Pharmaceuticals, Inc. Inhibitors of 11beta-hydroxysteroid dehydrogenase 1
CA2744946A1 (en) 2009-02-04 2010-08-12 Boehringer Ingelheim International Gmbh Cyclic inhibitors of 11.beta.-hydroxysteroid dehydrogenase 1
TW201039034A (en) * 2009-04-27 2010-11-01 Chunghwa Picture Tubes Ltd Pixel structure and the method of forming the same
US20100331320A1 (en) * 2009-04-30 2010-12-30 Vitae Pharmaceuticals, Inc. Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1
MA33216B1 (fr) 2009-04-30 2012-04-02 Boehringer Ingelheim Int Inhibiteurs cycliques de la 11béta-hydroxysteroïde déshydrogénase 1
EP2440537A1 (en) 2009-06-11 2012-04-18 Vitae Pharmaceuticals, Inc. Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 based on the 1,3 -oxazinan- 2 -one structure
JP5749263B2 (ja) 2009-07-01 2015-07-15 ヴァイティー ファーマシューティカルズ，インコーポレイテッド １１β−ヒドロキシステロイドデヒドロゲナーゼ１の環状インヒビター
EP2582698B1 (en) 2010-06-16 2016-09-14 Vitae Pharmaceuticals, Inc. Substituted 5-,6- and 7-membered heterocycles, medicaments containing such compounds, and their use
EP2585444B1 (en) 2010-06-25 2014-10-22 Boehringer Ingelheim International GmbH Azaspirohexanones as inhibitors of 11-beta-hsd1 for the treatment of metabolic disorders
CN103261202B (zh) * 2010-09-24 2016-01-20 阿迪维纳斯疗法有限公司 作为腺苷受体拮抗剂的稠合三环化合物
KR20130137628A (ko) 2010-11-02 2013-12-17 베링거 인겔하임 인터내셔날 게엠베하 대사 장애를 치료하기 위한 약제학적 병용물
WO2015027431A1 (en) * 2013-08-29 2015-03-05 Merck Sharp & Dohme Corp. 2,2-difluorodioxolo a2a receptor antagonists
US12414952B2 (en) 2018-11-20 2025-09-16 Merck Sharp & Dohme Llc Substituted amino triazolopyrimidine and amino triazolopyrazine adenosine receptor antagonists, pharmaceutical compositions and their use
CA3119774A1 (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
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
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

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995001356A1 (en) * 1993-06-29 1995-01-12 Schering-Plough S.P.A. 1,2,4-TRIAZOLO[1,5-c]PYRIMIDINE HETEROCYCLIC ANALOGUES HAVING ANTAGONISTIC ACTIVITY ON ADENOSINE A2 RECEPTOR
CN1255854A (zh) * 1997-05-21 2000-06-07 先灵一普劳有限公司 1,2,4－三唑并[1,5－c]嘧啶杂环类似物在制备用于治疗心血管疾病的药物中的用途

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3677445D1 (de) 1985-09-30 1991-03-14 Ciba Geigy Ag 2-substituierte-e-kondensierte(1,5-c)-pyrimidine, pharmazeutische zubereitungen und ihre verwendung.
AU612331B2 (en) * 1986-09-30 1991-07-11 Ciba-Geigy Ag 2-substituted-e-fused-(1,2,4)triazolo(1,5-c)pyrimidines pharmaceutical compositions
CA2144330A1 (en) * 1993-07-27 1995-02-09 Fumio Suzuki A therapeutic agent 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
JP4077155B2 (ja) * 1998-04-03 2008-04-16 株式会社大塚製薬工場 トリアゾロプリン誘導体、該誘導体を含有する医薬組成物、アデノシンａ３受容体親和剤および喘息治療剤
EP1227098B1 (en) 1999-09-28 2004-04-28 Otsuka Pharmaceutical Factory, Inc. Triazolopurine derivatives, drug compositions containing the same and adenosine a3 receptor affinitive agents
KR100520907B1 (ko) 2000-05-26 2005-10-11 쉐링 코포레이션 아데노신 Ａ2ａ수용체 길항제
IL161716A0 (en) 2001-11-30 2004-09-27 Schering Corp ADENOSINE A2a RECEPTOR ANTAGONISTS

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995001356A1 (en) * 1993-06-29 1995-01-12 Schering-Plough S.P.A. 1,2,4-TRIAZOLO[1,5-c]PYRIMIDINE HETEROCYCLIC ANALOGUES HAVING ANTAGONISTIC ACTIVITY ON ADENOSINE A2 RECEPTOR
CN1255854A (zh) * 1997-05-21 2000-06-07 先灵一普劳有限公司 1,2,4－三唑并[1,5－c]嘧啶杂环类似物在制备用于治疗心血管疾病的药物中的用途

Also Published As

Publication number Publication date
HUP0401777A2 (hu) 2004-12-28
HUP0401777A3 (en) 2008-06-30
AR037243A1 (es) 2004-11-03
CA2463598A1 (en) 2003-04-24
CA2463598C (en) 2009-09-08
EP1435960B1 (en) 2014-07-30
MXPA04003474A (es) 2004-07-30
WO2003032996A1 (en) 2003-04-24
KR100687954B1 (ko) 2007-02-27
CN1612736A (zh) 2005-05-04
US20030171381A1 (en) 2003-09-11
JP4545437B2 (ja) 2010-09-15
JP2005506352A (ja) 2005-03-03
MY124864A (en) 2006-07-31
IL160878A0 (en) 2004-08-31
PE20030477A1 (es) 2003-06-06
JP2008297312A (ja) 2008-12-11
KR20050035155A (ko) 2005-04-15
ZA200402812B (en) 2005-04-25
US6653315B2 (en) 2003-11-25
AU2002340184B2 (en) 2005-10-06
EP1435960A1 (en) 2004-07-14
NZ531761A (en) 2005-10-28

Similar Documents

Publication Publication Date Title
CN100421663C (zh) 咪唑并（4,3－E）,1,2,4－三唑并（1,5－C）嘧啶类化合物作为腺苷A2a受体拮抗剂
JP4574112B2 (ja) アデノシンａ２ａレセプターアンタゴニスト
AU2002340184A1 (en) Imidazo (4,3-E)-1,2,4-triazolo(1,5-C) pyrimidines as adenosine A2A receptor antagonists
JP4284182B2 (ja) アデノシンＡ２ａレセプターアンタゴニスト
JP4429724B2 (ja) ［１，２，４］−トリアゾール二環式アデノシンＡ２ａレセプタアンタゴニスト
EP1453835B1 (en) Adenosine a 2a receptor antagonists
EP1836205B1 (en) PYRAZOLO[1,5-A]PYRIMIDINE ADENOSINE A2a RECEPTOR ANTAGONISTS
JP2008524213A (ja) 新規なピラゾール誘導体及びニコチン性アセチルコリン受容体のモジュレーターとしてのそれらの使用
CN101273045A (zh) 7－[2－[4－(6－氟－3－甲基－1,2－苯并异噁唑－5－基)－1－哌嗪基]乙基]－2－(1－丙炔基)－7H－吡唑－[4,3－e]－[1,2,4]－三唑－[1,5－c]－嘧啶－5－胺
HK1108882B (en) Pyrazolo[1,5-a]pyrimidine adenosine a2a receptor antagonists
HK1063780B (en) Adenosine a2a receptor antagonists
HK1064100B (en) Adenosine a 2a receptor antagonists

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C14 Grant of patent or utility model
GR01 Patent grant
C17 Cessation of patent right
CF01 Termination of patent right due to non-payment of annual fee

Granted publication date: 20081001

Termination date: 20111011