CA2377746A1 - N-pyrazole a2a receptor agonists - Google Patents

N-pyrazole a2a receptor agonists Download PDF

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Publication number
CA2377746A1
CA2377746A1 CA002377746A CA2377746A CA2377746A1 CA 2377746 A1 CA2377746 A1 CA 2377746A1 CA 002377746 A CA002377746 A CA 002377746A CA 2377746 A CA2377746 A CA 2377746A CA 2377746 A1 CA2377746 A1 CA 2377746A1
Authority
CA
Canada
Prior art keywords
receptor agonists
pyrazole
compounds
purposes
adenosine
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.)
Granted
Application number
CA002377746A
Other languages
French (fr)
Other versions
CA2377746C (en
Inventor
Jeff A. Zablocki
Elfatih O. Elzein
Venkata P. Palle
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.)
Gilead Sciences Inc
Original Assignee
Cv Therapeutics, Inc.
Jeff A. Zablocki
Elfatih O. Elzein
Venkata P. Palle
Gilead Palo Alto, Inc.
Gilead Sciences, Inc.
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 Cv Therapeutics, Inc., Jeff A. Zablocki, Elfatih O. Elzein, Venkata P. Palle, Gilead Palo Alto, Inc., Gilead Sciences, Inc. filed Critical Cv Therapeutics, Inc.
Publication of CA2377746A1 publication Critical patent/CA2377746A1/en
Application granted granted Critical
Publication of CA2377746C publication Critical patent/CA2377746C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/16—Purine radicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • 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
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • 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
    • A61P9/08—Vasodilators for multiple indications
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
    • C07D473/32—Nitrogen atom
    • C07D473/34—Nitrogen atom attached in position 6, e.g. adenine

Abstract

2-adenosine N-pyrazole compounds having the following formula:

(see formula I) and methods for using the compounds as A2A receptor agonists to stimulate mammalian coronary vasodilation for therapeutic purposes and for purposes of imaging the heart.
CA002377746A 1999-06-22 2000-06-21 N-pyrazole a2a receptor agonists Expired - Lifetime CA2377746C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US09/338,185 US6403567B1 (en) 1999-06-22 1999-06-22 N-pyrazole A2A adenosine receptor agonists
US09/338,185 1999-06-22
PCT/US2000/040281 WO2000078779A2 (en) 1999-06-22 2000-06-21 N-pyrazole a2a receptor agonists

Publications (2)

Publication Number Publication Date
CA2377746A1 true CA2377746A1 (en) 2000-12-28
CA2377746C CA2377746C (en) 2007-04-10

Family

ID=23323763

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002377746A Expired - Lifetime CA2377746C (en) 1999-06-22 2000-06-21 N-pyrazole a2a receptor agonists

Country Status (27)

Country Link
US (9) US6403567B1 (en)
EP (1) EP1189916B1 (en)
JP (1) JP4727880B2 (en)
KR (1) KR100463300B1 (en)
CN (1) CN1167709C (en)
AR (1) AR024441A1 (en)
AT (1) ATE256141T1 (en)
AU (1) AU760806B2 (en)
BE (1) BE2011C004I2 (en)
BR (1) BRPI0011856B8 (en)
CA (1) CA2377746C (en)
CY (1) CY2011002I2 (en)
DE (2) DE60007127T2 (en)
DK (1) DK1189916T3 (en)
ES (1) ES2209974T3 (en)
FR (1) FR11C0004I2 (en)
HK (1) HK1044952B (en)
IL (2) IL147198A0 (en)
LU (1) LU91785I2 (en)
MX (1) MXPA01013325A (en)
NO (2) NO322457B1 (en)
NZ (1) NZ516334A (en)
PT (1) PT1189916E (en)
TR (1) TR200200588T2 (en)
TW (1) TWI230161B (en)
WO (1) WO2000078779A2 (en)
ZA (1) ZA200200301B (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8071566B2 (en) 2000-02-23 2011-12-06 Gilead Sciences, Inc. Methods of coronary imaging
US8106183B2 (en) 2006-02-03 2012-01-31 Gilead Sciences, Inc. Process for preparing an A2A-adenosine receptor agonist and its polymorphs
US8133879B2 (en) 2002-07-29 2012-03-13 Gilead Sciences, Inc. Myocardial perfusion imaging methods and compositions
US8183226B2 (en) 2002-07-29 2012-05-22 Gilead Sciences, Inc. Myocardial perfusion imaging method
US8278435B2 (en) 1999-06-22 2012-10-02 Gilead Sciences, Inc. N-pyrazole A2A receptor agonists
US8470801B2 (en) 2002-07-29 2013-06-25 Gilead Sciences, Inc. Myocardial perfusion imaging methods and compositions
USRE47351E1 (en) 1999-06-22 2019-04-16 Gilead Sciences, Inc. 2-(N-pyrazolo)adenosines with application as adenosine A2A receptor agonists

Families Citing this family (62)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6214807B1 (en) * 1999-06-22 2001-04-10 Cv Therapeutics, Inc. C-pyrazole 2A A receptor agonists
US20050059068A1 (en) * 2001-05-23 2005-03-17 Stratagene California Compositions and methods using dendrimer-treated microassays
US7262176B2 (en) 2001-08-08 2007-08-28 Cv Therapeutics, Inc. Adenosine A3 receptor agonists
US20030078232A1 (en) * 2001-08-08 2003-04-24 Elfatih Elzein Adenosine receptor A3 agonists
DE60333955D1 (en) 2002-02-15 2010-10-07 Gilead Palo Alto Inc Polymer coating for medical devices
WO2004022573A2 (en) 2002-09-09 2004-03-18 Cv Therapeutics, Inc. Adenosine a3 receptor agonists
EP1708721B1 (en) * 2004-01-27 2013-08-07 Gilead Sciences, Inc. Myocardial perfusion imaging using adenosine receptor agonists
TWI346109B (en) * 2004-04-30 2011-08-01 Otsuka Pharma Co Ltd 4-amino-5-cyanopyrimidine derivatives
WO2005117910A2 (en) * 2004-05-26 2005-12-15 Inotek Pharmaceuticals Corporation Purine derivatives as adenosine a1 receptor agonists and methods of use thereof
NZ554506A (en) * 2004-09-20 2011-01-28 Inotek Pharmaceuticals Corp Purine derivatives and methods of use thereof
US7655636B2 (en) * 2004-10-20 2010-02-02 Gilead Palo Alto, Inc. Use of A2A adenosine receptor agonists
GT200500281A (en) * 2004-10-22 2006-04-24 Novartis Ag ORGANIC COMPOUNDS.
GB0500785D0 (en) * 2005-01-14 2005-02-23 Novartis Ag Organic compounds
GB0505219D0 (en) * 2005-03-14 2005-04-20 Novartis Ag Organic compounds
JP5042996B2 (en) * 2005-05-19 2012-10-03 ギリアード・パロ・アルト・インコーポレイテッド A1 adenosine receptor agonist
NZ568392A (en) * 2005-11-30 2011-07-29 Inotek Pharmaceuticals Corp Purine derivatives and methods of use thereof
US20070183995A1 (en) * 2006-02-09 2007-08-09 Conopco, Inc., D/B/A Unilever Compounds useful as agonists of A2A adenosine receptors, cosmetic compositions with A2A agonists and a method for using the same
PL2013211T3 (en) 2006-04-21 2012-08-31 Novartis Ag Purine derivatives for use as adenosin a2a receptor agonists
GB0607944D0 (en) * 2006-04-21 2006-05-31 Novartis Ag Organic compounds
GB0607951D0 (en) * 2006-04-21 2006-05-31 Novartis Ag Organic compounds
GB0607950D0 (en) * 2006-04-21 2006-05-31 Novartis Ag Organic compounds
DE102006020349A1 (en) 2006-04-28 2007-10-31 Mahle International Gmbh Piston engine and associated operating method
US7691825B2 (en) * 2006-06-06 2010-04-06 King Pharmaceuticals Research And Development, Inc. Adenosine A2B receptor agonists
CA2655310A1 (en) * 2006-06-22 2008-05-29 Cv Therapeutics, Inc. Use of a2a adenosine receptor agonists in the treatment of ischemia
EP1889846A1 (en) * 2006-07-13 2008-02-20 Novartis AG Purine derivatives as A2a agonists
US20090081120A1 (en) * 2006-09-01 2009-03-26 Cv Therapeutics, Inc. Methods and Compositions for Increasing Patient Tolerability During Myocardial Imaging Methods
EP2056834B1 (en) * 2006-09-01 2012-08-29 Gilead Sciences, Inc. Methods and compositions for increasing patient tolerability during myocardial imaging methods
EP1903044A1 (en) * 2006-09-14 2008-03-26 Novartis AG Adenosine Derivatives as A2A Receptor Agonists
CA2663361A1 (en) * 2006-09-29 2008-04-10 Cv Therapeutics, Inc. Methods for myocardial imaging in patients having a history of pulmonary disease
EP2084121A1 (en) * 2006-11-10 2009-08-05 Novartis AG Cyclopentene diol monoacetate derivatives
EP2099360A2 (en) * 2007-01-03 2009-09-16 CV Therapeutics Inc. Myocardial perfusion imaging
WO2008133129A1 (en) * 2007-04-16 2008-11-06 Santen Pharmaceutical Co., Ltd. Therapeutic agent for glaucoma comprising adenosine a2a receptor agonist as active ingredient
KR20140041965A (en) * 2007-05-17 2014-04-04 씨브이 쎄러퓨틱스, 인코포레이티드 Process for preparing an a2a-adenosine receptor agonist and its polymorphs
RU2443708C2 (en) * 2007-05-17 2012-02-27 Си Ви Терапьютикс, Инк. Method of producing a2a-adenosine receptor agonist and polymorphic modifications thereof
US7868001B2 (en) * 2007-11-02 2011-01-11 Hutchison Medipharma Enterprises Limited Cytokine inhibitors
US7899039B2 (en) * 2008-02-15 2011-03-01 Cisco Technology, Inc. System and method for providing location and access network information support in a network environment
ES2562083T3 (en) * 2008-06-06 2016-03-02 Neurmedix, Inc. Methods for preparing 17-alkynyl-7-hydroxy-steroids and related compounds
MX2011003168A (en) * 2008-09-29 2011-05-19 Gilead Sciences Inc Combinations of a rate control agent and an a-2-alpha receptor antagonist for use in multidetector computed tomography methods.
US7957314B2 (en) * 2008-12-12 2011-06-07 Cisco Technology, Inc. System and method for provisioning charging and policy control in a network environment
EP2523669B1 (en) 2010-01-11 2016-12-07 Inotek Pharmaceuticals Corporation Combination, kit and method of reducing intraocular pressure
MX2012010724A (en) 2010-03-26 2012-11-12 Inotek Pharmaceuticals Corp Method of reducing intraocular pressure in humans using n6 -cyclopentyladenosine (cpa), cpa derivatives or prodrugs thereof.
US20130109645A1 (en) 2010-03-31 2013-05-02 The united States of America,as represented by Secretary,Dept.,of Health and Human Services Adenosine receptor agonists for the treatment and prevention of vascular or joint capsule calcification disorders
US9215588B2 (en) 2010-04-30 2015-12-15 Cisco Technology, Inc. System and method for providing selective bearer security in a network environment
JP2011098990A (en) * 2011-02-21 2011-05-19 Gilead Palo Alto Inc Myocardial perfusion imaging using adenosine receptor agonist
US8859522B2 (en) 2011-04-27 2014-10-14 Reliable Biopharmaceutical Corporation Processes for the preparation of regadenoson and a new crystalline form thereof
CZ308577B6 (en) * 2011-08-18 2020-12-16 Farmak, A. S. Process for preparing 2- (4-methoxy carbonyl pyrazol-1-yl) adenosine and 2- (4-ethoxycarbonylpyrazol-1-yl) adenosine
CZ304053B6 (en) 2011-08-22 2013-09-04 Farmak, A. S. Process for preparing 2-[4-[(methylamino)carbonyl]-1-H-pyrazol-1-yl]adenosine monohydrate
BR112014018413A8 (en) 2012-01-26 2017-07-11 Inotek Pharmaceuticals Corp METHYL NITRATE ANHYDRO POLYMORPHS [(2R,3S,4R,5R)-5-(6-(CYCLOPENTYLAMINO)-9H-PURIN-9-IL)-3,4-DIHYDROXITETRAHYDROFURAN-2-IL)] AND PREPARATION PROCESSES THE SAME
US20150290236A1 (en) * 2012-11-30 2015-10-15 Leiutis Pharmaceuticals Pvt. Ltd. Pharmaceutical compositions of regadenoson
SG11201506882YA (en) 2013-03-15 2015-09-29 Inotek Pharmaceuticals Corp Ophthalmic formulations
EP2789624B1 (en) 2013-04-11 2020-09-23 AMRI Italy S.r.l. Stable solid forms of regadenoson
CZ305213B6 (en) 2013-04-29 2015-06-10 Farmak, A. S. Polymorph E, 2-[4-[(methylamino)carbonyl]-1H-pyrazol-1-yl]adenosine and process for its preparation
EP3003320A4 (en) 2013-05-30 2016-10-19 Biophore India Pharmaceuticals Pvt Ltd Novel polymorph of regadenoson
CN104513241B (en) * 2013-09-30 2017-02-08 浙江海正药业股份有限公司 New regadenoson intermediate, preparation method and application thereof
CN104744540A (en) * 2013-12-26 2015-07-01 上海紫源制药有限公司 Preparation method for regadenoson
CN105085593A (en) * 2014-04-21 2015-11-25 上海紫源制药有限公司 Regadenoson crystal form and preparation method thereof
WO2016126734A1 (en) 2015-02-06 2016-08-11 Apicore Us Llc Process of making regadenoson and novel polymorph thereof
US9809617B2 (en) 2015-07-03 2017-11-07 Shanghai Ziyuan Pharmaceutical Co., Ltd. Crystal form of regadenoson and preparation method thereof
CN106397442B (en) * 2015-07-28 2020-03-27 国药集团国瑞药业有限公司 Purification method of regadenoson
CA3049856C (en) 2017-01-13 2021-10-26 Tobishi Pharmaceutical Co., Ltd. Neutrophil activation regulator
WO2019191389A1 (en) 2018-03-29 2019-10-03 Johnson Matthey Public Limited Company Solid-state forms of regadenoson, their use and preparation
US10815265B2 (en) 2018-06-29 2020-10-27 Usv Private Limited Process for preparation of regadenoson and polymorphs thereof

Family Cites Families (86)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK135130B (en) 1970-12-28 1977-03-07 Takeda Chemical Industries Ltd Analogous process for the preparation of 2-substituted adenosine derivatives or acid addition salts thereof.
BE787064A (en) 1971-08-03 1973-02-01 Philips Nv MAGNETIC DEVICE CONTAINING DOMAINS
US3845770A (en) * 1972-06-05 1974-11-05 Alza Corp Osmatic dispensing device for releasing beneficial agent
US4089959A (en) * 1976-03-31 1978-05-16 Cooper Laboratories, Inc. Long-acting xanthine bronchodilators and antiallergy agents
US4120947A (en) * 1976-03-31 1978-10-17 Cooper Laboratories, Inc. Xanthine compounds and method of treating bronchospastic and allergic diseases
SE7810946L (en) * 1978-10-20 1980-04-21 Draco Ab METHOD OF TREATING CHRONIC OBSTRUCTIVE AIR DISEASE
US4326525A (en) * 1980-10-14 1982-04-27 Alza Corporation Osmotic device that improves delivery properties of agent in situ
US4593095A (en) * 1983-02-18 1986-06-03 The Johns Hopkins University Xanthine derivatives
US5364620A (en) * 1983-12-22 1994-11-15 Elan Corporation, Plc Controlled absorption diltiazem formulation for once daily administration
US4696932A (en) * 1984-10-26 1987-09-29 The United States Of America As Represented By The Department Of Health And Human Services Biologically-active xanthine derivatives
JPS6299395A (en) 1985-10-25 1987-05-08 Yamasa Shoyu Co Ltd 2-alkinyladenosine and antihypertensive
US4968697A (en) * 1987-02-04 1990-11-06 Ciba-Geigy Corporation 2-substituted adenosine 5'-carboxamides as antihypertensive agents
US5001139A (en) * 1987-06-12 1991-03-19 American Cyanamid Company Enchancers for the transdermal flux of nivadipine
US4992445A (en) * 1987-06-12 1991-02-12 American Cyanamid Co. Transdermal delivery of pharmaceuticals
US4990498A (en) * 1988-04-26 1991-02-05 Temple University-Of The Commonwealth System Of Higher Education 2- and 8-azido(2'-5')oligoadenylates and antiviral uses thereof
US4902514A (en) * 1988-07-21 1990-02-20 Alza Corporation Dosage form for administering nilvadipine for treating cardiovascular symptoms
US5070877A (en) 1988-08-11 1991-12-10 Medco Research, Inc. Novel method of myocardial imaging
DE3831430A1 (en) * 1988-09-15 1990-03-22 Bayer Ag SUBSTITUTED 4-HETEROCYCLYLOXIMINO-PYRAZOLIN-5-ONE, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS A PEST CONTROL
EP0444196B1 (en) 1988-11-15 1994-06-08 Yamasa Shoyu Kabushiki Kaisha Agent for treatment and prophylaxis of ischemic disease of heart or brain
IT1229195B (en) 1989-03-10 1991-07-25 Poli Ind Chimica Spa XANTHINIC DERIVATIVES WITH BRONCODILATORY ACTIVITY AND THEIR THERAPEUTIC APPLICATIONS.
CA2035038C (en) 1989-06-20 1998-12-29 Toyofumi Yamaguchi Synthetic intermediates of 2-alkynyladenosines, processes for preparing the synthetic intermediates, processes for preparing 2-alkynyladenosines utilizing the synthetic intermediates, and stable 2-alkynyladenosine derivatives
US5032252A (en) * 1990-04-27 1991-07-16 Mobil Oil Corporation Process and apparatus for hot catalyst stripping in a bubbling bed catalyst regenerator
DE4019892A1 (en) 1990-06-22 1992-01-02 Boehringer Ingelheim Kg New xanthine derivs. are selective A1 adenosine antagonists - useful for treating CNS disorders (e.g. senile dementia) and heart and circulation disorders
US5189027A (en) 1990-11-30 1993-02-23 Yamasa Shoyu Kabushiki Kaisha 2-substituted adenosine derivatives and pharmaceutical compositions for circulatory diseases
FR2671356B1 (en) 1991-01-09 1993-04-30 Inst Nat Sante Rech Med METHOD FOR DESCRIBING ANTIBODY (AB) DIRECTORIES AND T CELL RECEPTORS (TCR) IN THE INDIVIDUAL'S IMMUNE SYSTEM.
JP2740362B2 (en) 1991-02-12 1998-04-15 ヤマサ醤油株式会社 Stable solid 2-octynyl adenosine and process for its preparation
JP3053908B2 (en) 1991-06-28 2000-06-19 ヤマサ醤油株式会社 2-alkynyl adenosine derivatives
US5516894A (en) * 1992-03-11 1996-05-14 The General Hospital Corporation A2b -adenosine receptors
IT1254915B (en) 1992-04-24 1995-10-11 Gloria Cristalli ADENOSINE DERIVATIVES FOR ACTIVITY A2 AGONIST
GB9210839D0 (en) 1992-05-21 1992-07-08 Smithkline Beecham Plc Novel compounds
JPH08500967A (en) 1992-06-12 1996-02-06 ガーヴァン インスティチュート オブ メディカル リサーチ DNA sequences encoding human A1, A2a and A2b adenosine receptors
US5705491A (en) 1992-10-27 1998-01-06 Nippon Zoki Pharmaceutical Co., Ltd. Adenosine deaminase inhibitor
CA2112031A1 (en) * 1992-12-24 1994-06-25 Fumio Suzuki Xanthine derivatives
US5477857A (en) 1993-09-10 1995-12-26 Discovery Therapeutics, Inc. Diagnostic uses of hydrazinoadenosines
WO1995011681A1 (en) 1993-10-29 1995-05-04 Merck & Co., Inc. Human adenosine receptor antagonists
EP0698607B1 (en) * 1994-02-23 2002-05-29 Kyowa Hakko Kogyo Kabushiki Kaisha Xanthine derivative
US5704491A (en) * 1995-07-21 1998-01-06 Cummins-Allison Corp. Method and apparatus for discriminating and counting documents
US5646156A (en) * 1994-04-25 1997-07-08 Merck & Co., Inc. Inhibition of eosinophil activation through A3 adenosine receptor antagonism
US6448235B1 (en) * 1994-07-11 2002-09-10 University Of Virginia Patent Foundation Method for treating restenosis with A2A adenosine receptor agonists
US5877180A (en) * 1994-07-11 1999-03-02 University Of Virginia Patent Foundation Method for treating inflammatory diseases with A2a adenosine receptor agonists
US6514949B1 (en) * 1994-07-11 2003-02-04 University Of Virginia Patent Foundation Method compositions for treating the inflammatory response
US5854081A (en) * 1996-06-20 1998-12-29 The University Of Patent Foundation Stable expression of human A2B adenosine receptors, and assays employing the same
US5780481A (en) * 1996-08-08 1998-07-14 Merck & Co., Inc. Method for inhibiting activation of the human A3 adenosine receptor to treat asthma
US5776960A (en) * 1996-10-16 1998-07-07 Buckman Laboratories International, Inc. Synergistic antimicrobial compositions containing an ionene polymer and a pyrithione salt and methods of using the same
US5770716A (en) 1997-04-10 1998-06-23 The Perkin-Elmer Corporation Substituted propargylethoxyamido nucleosides, oligonucleotides and methods for using same
AU7449598A (en) 1997-05-23 1998-12-11 Nippon Shinyaku Co. Ltd. Medicinal composition for prevention or treatment of hepatopathy
EP1014995A4 (en) 1997-06-18 2005-02-16 Aderis Pharmaceuticals Inc Compositions and methods for preventing restenosis following revascularization procedures
US6026317A (en) 1998-02-06 2000-02-15 Baylor College Of Medicine Myocardial perfusion imaging during coronary vasodilation with selective adenosine A2 receptor agonists
US6117878A (en) * 1998-02-24 2000-09-12 University Of Virginia 8-phenyl- or 8-cycloalkyl xanthine antagonists of A2B human adenosine receptors
CA2316994A1 (en) 1998-06-08 1999-12-16 Epigenesis Pharmaceuticals, Inc. Composition and method for prevention and treatment of cardiopulmonary and renal failure or damage associated with ischemia, endotoxin release, ards or brought about by administration of certain drugs
US6322771B1 (en) * 1999-06-18 2001-11-27 University Of Virginia Patent Foundation Induction of pharmacological stress with adenosine receptor agonists
US6214807B1 (en) * 1999-06-22 2001-04-10 Cv Therapeutics, Inc. C-pyrazole 2A A receptor agonists
US6403567B1 (en) * 1999-06-22 2002-06-11 Cv Therapeutics, Inc. N-pyrazole A2A adenosine receptor agonists
EP1208100B1 (en) 1999-08-31 2003-04-02 Vanderbilt University Selective antagonists of a2b adenosine receptors
US6368573B1 (en) * 1999-11-15 2002-04-09 King Pharmaceuticals Research And Development, Inc. Diagnostic uses of 2-substituted adenosine carboxamides
US6294522B1 (en) * 1999-12-03 2001-09-25 Cv Therapeutics, Inc. N6 heterocyclic 8-modified adenosine derivatives
US6605597B1 (en) * 1999-12-03 2003-08-12 Cv Therapeutics, Inc. Partial or full A1agonists-N-6 heterocyclic 5′-thio substituted adenosine derivatives
US6677336B2 (en) * 2000-02-22 2004-01-13 Cv Therapeutics, Inc. Substituted piperazine compounds
US6552023B2 (en) * 2000-02-22 2003-04-22 Cv Therapeutics, Inc. Aralkyl substituted piperazine compounds
CA2439222C (en) * 2000-02-23 2009-07-14 Cv Therapeutics, Inc. Identification of partial agonists of the a2a adenosine receptor
US6387913B1 (en) * 2000-12-07 2002-05-14 S. Jamal Mustafa Method of treating airway diseases with combined administration of A2B and A3 adenosine receptor antagonists
US6670334B2 (en) * 2001-01-05 2003-12-30 University Of Virginia Patent Foundation Method and compositions for treating the inflammatory response
US6995148B2 (en) * 2001-04-05 2006-02-07 University Of Pittsburgh Adenosine cyclic ketals: novel adenosine analogues for pharmacotherapy
US6599283B1 (en) * 2001-05-04 2003-07-29 Cv Therapeutics, Inc. Method of preventing reperfusion injury
ATE459598T1 (en) * 2001-05-14 2010-03-15 Novartis Ag SULFONAMIDE DERIVATIVES
ATE520694T1 (en) * 2001-11-09 2011-09-15 Gilead Palo Alto Inc A2B ADENOSINE RECEPTOR ANTAGONISTS
US7125993B2 (en) * 2001-11-09 2006-10-24 Cv Therapeutics, Inc. A2B adenosine receptor antagonists
US6977300B2 (en) * 2001-11-09 2005-12-20 Cv Therapeutics, Inc. A2B adenosine receptor antagonists
WO2003053366A2 (en) * 2001-12-20 2003-07-03 Osi Pharmaceuticals, Inc. Pyrimidine a2b selective antagonist compounds, their synthesis and use
WO2003086451A1 (en) * 2002-04-05 2003-10-23 Centocor, Inc. Asthma-related anti-il-13 immunoglobulin derived proteins, compositions, methods and uses
EP1494685B1 (en) 2002-04-18 2008-12-31 Cv Therapeutics, Inc. Method of treating arrhythmias comprising administration of an a1 adenosine agonist with a beta blocker
US20050020915A1 (en) * 2002-07-29 2005-01-27 Cv Therapeutics, Inc. Myocardial perfusion imaging methods and compositions
CA2492855C (en) 2002-07-29 2012-09-18 Cv Therapeutics, Inc. Myocardial perfusion imaging using a2a receptor agonists
EP1708721B1 (en) 2004-01-27 2013-08-07 Gilead Sciences, Inc. Myocardial perfusion imaging using adenosine receptor agonists
AU2005295654B2 (en) * 2004-10-15 2011-04-14 Gilead Sciences, Inc. Method of preventing and treating airway remodeling and pulmonary inflammation using A2B adenosine receptor antagonists
US7655636B2 (en) 2004-10-20 2010-02-02 Gilead Palo Alto, Inc. Use of A2A adenosine receptor agonists
US20060159621A1 (en) * 2005-01-12 2006-07-20 Barrett Richard J Method of detecting myocardial dysfunction in patients having a history of asthma or bronchospasm
AU2007212542B2 (en) * 2006-02-03 2013-01-31 Gilead Sciences, Inc. Process for preparing an A2A-Adenosine receptor agonist and its polymorphs
CA2655310A1 (en) 2006-06-22 2008-05-29 Cv Therapeutics, Inc. Use of a2a adenosine receptor agonists in the treatment of ischemia
EP2056834B1 (en) * 2006-09-01 2012-08-29 Gilead Sciences, Inc. Methods and compositions for increasing patient tolerability during myocardial imaging methods
US20090081120A1 (en) * 2006-09-01 2009-03-26 Cv Therapeutics, Inc. Methods and Compositions for Increasing Patient Tolerability During Myocardial Imaging Methods
CA2663361A1 (en) * 2006-09-29 2008-04-10 Cv Therapeutics, Inc. Methods for myocardial imaging in patients having a history of pulmonary disease
EP2099360A2 (en) * 2007-01-03 2009-09-16 CV Therapeutics Inc. Myocardial perfusion imaging
KR20140041965A (en) 2007-05-17 2014-04-04 씨브이 쎄러퓨틱스, 인코포레이티드 Process for preparing an a2a-adenosine receptor agonist and its polymorphs
WO2009076580A2 (en) 2007-12-12 2009-06-18 Thomas Jefferson University Compositions and methods for the treatment and prevention of cardiovascular diseases
MX2011003168A (en) * 2008-09-29 2011-05-19 Gilead Sciences Inc Combinations of a rate control agent and an a-2-alpha receptor antagonist for use in multidetector computed tomography methods.

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8278435B2 (en) 1999-06-22 2012-10-02 Gilead Sciences, Inc. N-pyrazole A2A receptor agonists
USRE47351E1 (en) 1999-06-22 2019-04-16 Gilead Sciences, Inc. 2-(N-pyrazolo)adenosines with application as adenosine A2A receptor agonists
US9045519B2 (en) 1999-06-22 2015-06-02 Gilead Sciences, Inc. N-pyrazole A2A receptor agonists
US8569260B2 (en) 1999-06-22 2013-10-29 Gilead Sciences, Inc. N-pyrazole A2A receptor agonists
US9163057B2 (en) 2000-02-23 2015-10-20 Gilead Sciences, Inc. Methods of myocardial perfusion imaging
US8071566B2 (en) 2000-02-23 2011-12-06 Gilead Sciences, Inc. Methods of coronary imaging
US8470801B2 (en) 2002-07-29 2013-06-25 Gilead Sciences, Inc. Myocardial perfusion imaging methods and compositions
US8183226B2 (en) 2002-07-29 2012-05-22 Gilead Sciences, Inc. Myocardial perfusion imaging method
US8906878B2 (en) 2002-07-29 2014-12-09 Gilead Sciences, Inc. Myocardial perfusion imaging methods and compositions
US8133879B2 (en) 2002-07-29 2012-03-13 Gilead Sciences, Inc. Myocardial perfusion imaging methods and compositions
US9289446B2 (en) 2002-07-29 2016-03-22 Gilead Sciences, Inc. Myocardial perfusion imaging methods and compositions
US8268988B2 (en) 2006-02-03 2012-09-18 Gilead Sciences, Inc. Process for preparing an A2A-adenosine receptor agonist and its polymorphs
US8524883B2 (en) 2006-02-03 2013-09-03 Gilead Sciences, Inc. Monohydrate of (1-{9-[4S,2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-aminopurin-2-yl}pyrazol-4-yl)-N-methylcarboxamide
US9085601B2 (en) 2006-02-03 2015-07-21 Gilead Sciences, Inc. Process for preparing an A2A-adenosine receptor agonist and its polymorphs
USRE47301E1 (en) 2006-02-03 2019-03-19 Gilead Sciences, Inc. Process for preparing an A2A-adenosine receptor agonist and its polymorphs
US8106183B2 (en) 2006-02-03 2012-01-31 Gilead Sciences, Inc. Process for preparing an A2A-adenosine receptor agonist and its polymorphs

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