CA2093502A1 - Hydrazoadenosines - Google Patents

Hydrazoadenosines

Info

Publication number
CA2093502A1
CA2093502A1 CA002093502A CA2093502A CA2093502A1 CA 2093502 A1 CA2093502 A1 CA 2093502A1 CA 002093502 A CA002093502 A CA 002093502A CA 2093502 A CA2093502 A CA 2093502A CA 2093502 A1 CA2093502 A1 CA 2093502A1
Authority
CA
Canada
Prior art keywords
linear
hydrogen
branched alkyl
present
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
CA002093502A
Other languages
French (fr)
Other versions
CA2093502C (en
Inventor
Ray A. Olsson
Robert D. Thompson
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.)
Aderis Pharmaceuticals Inc
Original Assignee
Ray A. Olsson
Robert D. Thompson
Whitby Research, Inc.
Discovery Therapeutics, Inc.
Aderis Pharmaceuticals, 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 Ray A. Olsson, Robert D. Thompson, Whitby Research, Inc., Discovery Therapeutics, Inc., Aderis Pharmaceuticals, Inc. filed Critical Ray A. Olsson
Publication of CA2093502A1 publication Critical patent/CA2093502A1/en
Application granted granted Critical
Publication of CA2093502C publication Critical patent/CA2093502C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

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
    • 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
    • A61P9/08—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

Abstract

The present invention discloses a compound of the formula:
(see formula one) where R1 is hydrogen or the group -C(R3)(R5)-R4, where R3 and R4 are the same or different and are hydrogen, C1 to C12 linear or branched alkyl, C3 to C7 cycloalkyl, C6 to C10 aryl unsubstituted or substituted with C1 to C6 linear or branched alkyl, C1 to C6 linear or branched alkoxy, nitro, amino, amino substituted with at least one C1 to C6 linear or branched alkyl or phenyl, C2 to C10 aralkyl, C4 to C8 heteroaryl wherein said heteroatom is nitrogen, phosphorous, sulfur or oxygen, and R2 is hydrogen, or taken together with R5, forms a chemical bond, and R is a monosaccharide radical selected from the group consisting essentially of glucose, fructose, ribose, 2-deoxyribose, mannose, galactose, xylose and arabinose. The compounds prepared by the present invention are therapeutically effective adenosine receptor agonists in mammals. Thus, they are effective for treating conditions which respond to selective adenosine A2 receptor stimulation (particularly adenosine-2). Accordingly, the compounds of the present invention are useful for treating hypertension, thrombosis and atherosclerosis and for causing coronary vasodilation.
CA002093502A 1992-04-24 1993-04-06 Hydrazoadenosines Expired - Lifetime CA2093502C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US873,440 1992-04-24
US07/873,440 US5278150A (en) 1992-04-24 1992-04-24 2-hydrazoadenosines and their utility for the treatmeat of vascular conditions

Publications (2)

Publication Number Publication Date
CA2093502A1 true CA2093502A1 (en) 1993-10-25
CA2093502C CA2093502C (en) 2004-06-22

Family

ID=25361637

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002093502A Expired - Lifetime CA2093502C (en) 1992-04-24 1993-04-06 Hydrazoadenosines

Country Status (5)

Country Link
US (1) US5278150A (en)
EP (1) EP0567094B1 (en)
JP (1) JP3395912B2 (en)
CA (1) CA2093502C (en)
DE (1) DE69323643T2 (en)

Families Citing this family (43)

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US5477857A (en) * 1993-09-10 1995-12-26 Discovery Therapeutics, Inc. Diagnostic uses of hydrazinoadenosines
US6514949B1 (en) 1994-07-11 2003-02-04 University Of Virginia Patent Foundation Method compositions for treating the inflammatory response
US5877180A (en) * 1994-07-11 1999-03-02 University Of Virginia Patent Foundation Method for treating inflammatory diseases with A2a adenosine receptor agonists
US6448235B1 (en) 1994-07-11 2002-09-10 University Of Virginia Patent Foundation Method for treating restenosis with A2A adenosine receptor agonists
US5817641A (en) * 1994-07-21 1998-10-06 Thomas Jefferson University Treatment of enterotoxigenic diarrhea with 2-substituted adenosine derivatives
CA2295195C (en) 1997-06-18 2009-12-15 Discovery Therapeutics, Inc. Compositions and methods for preventing restenosis following revascularization procedures
US5972903A (en) * 1997-10-07 1999-10-26 Regents Of The University Of California Corporation Method for promoting angiogenesis using heparin and adenosine
JP2003506310A (en) 1997-10-07 2003-02-18 リージェンツ オブ ザ ユニバーシティー オブ カリフォルニア Treatment of occlusive peripheral vascular disease and coronary artery disease with a combination of heparin and an adenosine A2 agonist or with adenosine
US6117878A (en) * 1998-02-24 2000-09-12 University Of Virginia 8-phenyl- or 8-cycloalkyl xanthine antagonists of A2B human adenosine receptors
US7427606B2 (en) * 1999-02-01 2008-09-23 University Of Virginia Patent Foundation Method to reduce inflammatory response in transplanted tissue
US6232297B1 (en) 1999-02-01 2001-05-15 University Of Virginia Patent Foundation Methods and compositions for treating inflammatory response
US7378400B2 (en) * 1999-02-01 2008-05-27 University Of Virginia Patent Foundation Method to reduce an inflammatory response from arthritis
US6322771B1 (en) 1999-06-18 2001-11-27 University Of Virginia Patent Foundation Induction of pharmacological stress with adenosine receptor agonists
DE10041478A1 (en) * 2000-08-24 2002-03-14 Sanol Arznei Schwarz Gmbh New pharmaceutical composition
US6670334B2 (en) 2001-01-05 2003-12-30 University Of Virginia Patent Foundation Method and compositions for treating the inflammatory response
GB2372742A (en) * 2001-03-03 2002-09-04 Univ Leiden C2,5'-Disubstituted and N6,C2,5'-trisubstituted adenosine derivatives and their different uses
GB2372741A (en) * 2001-03-03 2002-09-04 Univ Leiden C2,8-Disubstituted adenosine derivatives and their different uses
US20030027793A1 (en) * 2001-05-08 2003-02-06 Thomas Lauterback Transdermal treatment of parkinson's disease
US20030026830A1 (en) * 2001-05-08 2003-02-06 Thomas Lauterback Transdermal therapeutic system for parkinson's disease inducing high plasma levels of rotigotine
JP4514452B2 (en) * 2001-10-01 2010-07-28 ユニバーシティ オブ バージニア パテント ファウンデーション 2-propyladenosine analogs having A2A agonist activity and compositions thereof
AU2003263846B2 (en) * 2002-08-15 2009-12-17 Gilead Palo Alto, Inc. Partial and full agonists of A1 adenosine receptors
US20050033044A1 (en) * 2003-05-19 2005-02-10 Bristol-Myers Squibb Pharma Company Methods for preparing 2-alkynyladenosine derivatives
KR101267202B1 (en) * 2004-05-26 2013-05-24 이노텍 파마슈티컬스 코포레이션 Purine derivatives as adenosine a1 receptor agonists and methods of use thereof
WO2006015357A2 (en) 2004-08-02 2006-02-09 University Of Virginia Patent Foundation 2-propynyl adenosine analogs with modified 5'-ribose groups having a2a agonist activity
WO2006023272A1 (en) * 2004-08-02 2006-03-02 University Of Virginia Patent Foundation 2-polycyclic propynyl adenosine analogs having a2a agonist activity
WO2006028618A1 (en) * 2004-08-02 2006-03-16 University Of Virginia Patent Foundation 2-polycyclic propynyl adenosine analogs with modified 5'-ribose groups having a2a agonist activity
JP5011112B2 (en) * 2004-09-20 2012-08-29 イノテック ファーマシューティカルズ コーポレイション Pharmaceuticals for the treatment of inflammatory diseases containing purine derivatives
EP1841355A4 (en) * 2005-01-12 2012-09-05 King Pharmaceuticals Res & Dev Method of detecting myocardial dysfunction in patients having a history of asthma or bronchospasm
NZ568694A (en) 2005-11-09 2011-09-30 Zalicus Inc Method, compositions, and kits for the treatment of medical conditions
JP5203214B2 (en) * 2005-11-30 2013-06-05 イノテック ファーマシューティカルズ コーポレイション Purine compounds and methods of use thereof
US20080027022A1 (en) * 2006-02-08 2008-01-31 Linden Joel M Method to treat gastric lesions
WO2007120972A2 (en) 2006-02-10 2007-10-25 University Of Virginia Patent Foundation Method to treat sickle cell disease
US8188063B2 (en) * 2006-06-19 2012-05-29 University Of Virginia Patent Foundation Use of adenosine A2A modulators to treat spinal cord injury
JP2008285478A (en) * 2007-04-16 2008-11-27 Santen Pharmaceut Co Ltd Therapeutic agent for glaucoma comprising adenosine a2a receptor agonist as effective component
US7558455B2 (en) * 2007-06-29 2009-07-07 Ethicon Endo-Surgery, Inc Receiver aperture broadening for scanned beam imaging
US8058259B2 (en) * 2007-12-20 2011-11-15 University Of Virginia Patent Foundation Substituted 4-{3-[6-amino-9-(3,4-dihydroxy-tetrahydro-furan-2-yl)-9H-purin-2-yl]-prop-2-ynyl}-piperidine-1-carboxylic acid esters as A2AR agonists
US20110044904A1 (en) * 2008-02-29 2011-02-24 Moorman Allan R Crystal forms of 2--adenosine
CN102014959B (en) 2008-03-10 2016-01-20 康奈尔大学 The adjustment of blood-brain barrier permeability
KR20120115344A (en) 2010-01-11 2012-10-17 이노텍 파마슈티컬스 코포레이션 Combination, kit and method of reducing intraocular pressure
BR112012023749A2 (en) 2010-03-26 2016-08-23 Inotek Pharmaceuticals Corp method for reducing intraocular pressure in humans using n6-cyclopentyladenosine (cpa), cpa derivatives or prodrugs thereof
MX2014009086A (en) 2012-01-26 2015-06-05 Inotek Pharmaceuticals Corp Anhydrous polymorphs of (2r,3s,4r,5r)-5-(6-(cyclopentylamino)-9h- purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl) } methyl nitrate and processes of preparation thereof.
WO2014152723A1 (en) 2013-03-15 2014-09-25 Inotek Pharmaceuticals Corporation Ophthalmic formulations
US20220378816A1 (en) * 2019-06-21 2022-12-01 Academy Of Military Medical Sciences 2-benzylidene hydrazinoadenosine compounds having a2a adenosine receptor agonistic activity

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4224438A (en) * 1970-07-14 1980-09-23 Boehringer Mannheim Gmbh Adenosine-5'-carboxylic acid amides
DE2034785A1 (en) * 1970-07-14 1972-01-20 Boehnnger Mannheim GmbH, 6800 Mann heim Waldhof Adenosine 5 carboxylic acid derivatives
JPS4935635B1 (en) * 1970-12-28 1974-09-25
US4140851A (en) * 1977-11-21 1979-02-20 The United States Of America As Represented By The Department Of Health, Education And Welfare Synthesis and antitumor activity of 2,4,5-trisubstituted-pyrrolo2,3-d]-pyrimidine nucleosides
JP2619710B2 (en) * 1989-02-27 1997-06-11 日本製紙 株式会社 Method for producing 2 ', 3'-dideoxypurine nucleosides
US5155098A (en) * 1989-06-09 1992-10-13 Hoechst-Roussel Pharmaceuticals Inc. N-heteroaryl-purin-6-amines, and pharmaceutical compositions and methods employing them

Also Published As

Publication number Publication date
EP0567094A2 (en) 1993-10-27
EP0567094A3 (en) 1994-03-30
JP3395912B2 (en) 2003-04-14
CA2093502C (en) 2004-06-22
DE69323643D1 (en) 1999-04-08
EP0567094B1 (en) 1999-03-03
US5278150A (en) 1994-01-11
DE69323643T2 (en) 1999-07-29
JPH06128281A (en) 1994-05-10

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