HUP0500455A2 - Parciális és teljes A1-agonisták N6-heterociklusos-5'-tiocsoporttal szubsztituált adenozinszármazékok - Google Patents

Parciális és teljes A1-agonisták N6-heterociklusos-5'-tiocsoporttal szubsztituált adenozinszármazékok

Info

Publication number
HUP0500455A2
HUP0500455A2 HU0500455A HUP0500455A HUP0500455A2 HU P0500455 A2 HUP0500455 A2 HU P0500455A2 HU 0500455 A HU0500455 A HU 0500455A HU P0500455 A HUP0500455 A HU P0500455A HU P0500455 A2 HUP0500455 A2 HU P0500455A2
Authority
HU
Hungary
Prior art keywords
group
partial
full
heterocyclic
agonists
Prior art date
Application number
HU0500455A
Other languages
English (en)
Inventor
Jeff A. Zablocki
Venkata P. Palle
Vaibhav Varkhedkar
Luiz Belardinelli
Prabha N. Ibrahim
Original Assignee
Cv Therapeutics, 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. filed Critical Cv Therapeutics, Inc.
Publication of HUP0500455A2 publication Critical patent/HUP0500455A2/hu

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    • 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
    • C07H19/167—Purine radicals with ribosyl as the saccharide radical
    • 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
    • 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
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • 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
    • A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
    • 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

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Cardiology (AREA)
  • Diabetes (AREA)
  • Molecular Biology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Genetics & Genomics (AREA)
  • Biotechnology (AREA)
  • Biochemistry (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Neurology (AREA)
  • Endocrinology (AREA)
  • Pain & Pain Management (AREA)
  • Child & Adolescent Psychology (AREA)
  • Emergency Medicine (AREA)
  • Hospice & Palliative Care (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Saccharide Compounds (AREA)
  • Medicinal Preparation (AREA)

Abstract

A találmány tárgyát képezik az (Ia) általános képletű vegyületek, azokelőállítása és alkalmazásuk. Az (Ia) képletben X1 jelentése S, S(O)vagy S(O)2 képletű csoport; R1 jelentése heterociklusos csoport,amelynek legalább az egyik szénatomját nitrogén-, oxigén- vagyfoszforatom, vagy S(O)0-2 csoport helyettesíti; R2 jelentése hidrogén-vagy halogénatom, CF3 vagy cianocsoport; R3 és R4 jelentése egymástólfüggetlenül alkil-, alkenil-, alkinilcsoport, heterociklil-, aril-vagy heteroarilcsoport, amelyek önmagukban is 1-3 szubsztituensthordozhatnak; R5 jelentése alkil-, alkenil-, alkinil-, heterociklil-,aril vagy heteroarilcsoport, amelyek önmagukban is 1-3 szubsztituensthordozhatnak. A találmány szerinti vegyületek parciális vagy teljesadenozin A1-receptoragonisták; ennek alapján a koszorúerekaktivitásának növelésére, a szívizomsejtek funkciójának módosítására,központi idegrendszeri megbetegedések és cukorbetegség kezelésérealkalmazhatók.
HU0500455A 1999-12-03 2000-12-01 Parciális és teljes A1-agonisták N6-heterociklusos-5'-tiocsoporttal szubsztituált adenozinszármazékok HUP0500455A2 (hu)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US09/454,136 US6605597B1 (en) 1999-12-03 1999-12-03 Partial or full A1agonists-N-6 heterocyclic 5′-thio substituted adenosine derivatives
PCT/US2000/032721 WO2001040246A1 (en) 1999-12-03 2000-12-01 Partial or full a1 agonists - n6 heterocyclic 5'-thio substituted adenosine derivatives

Publications (1)

Publication Number Publication Date
HUP0500455A2 true HUP0500455A2 (hu) 2005-08-29

Family

ID=23803455

Family Applications (1)

Application Number Title Priority Date Filing Date
HU0500455A HUP0500455A2 (hu) 1999-12-03 2000-12-01 Parciális és teljes A1-agonisták N6-heterociklusos-5'-tiocsoporttal szubsztituált adenozinszármazékok

Country Status (25)

Country Link
US (2) US6605597B1 (hu)
EP (1) EP1233973B1 (hu)
JP (1) JP4021195B2 (hu)
KR (1) KR100484988B1 (hu)
CN (1) CN1152042C (hu)
AR (1) AR029199A1 (hu)
AT (1) ATE254133T1 (hu)
AU (3) AU4138701A (hu)
BR (1) BR0016126A (hu)
CA (1) CA2389264C (hu)
CZ (1) CZ20013705A3 (hu)
DE (1) DE60006576T2 (hu)
DK (1) DK1233973T3 (hu)
ES (1) ES2208437T3 (hu)
HK (1) HK1047941A1 (hu)
HU (1) HUP0500455A2 (hu)
IL (1) IL145903A (hu)
MX (1) MXPA01011113A (hu)
NO (1) NO20015373L (hu)
NZ (1) NZ514777A (hu)
PT (1) PT1233973E (hu)
TR (2) TR200301971T4 (hu)
TW (1) TWI249536B (hu)
WO (2) WO2001040243A2 (hu)
ZA (1) ZA200204380B (hu)

Families Citing this family (42)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
USRE47351E1 (en) 1999-06-22 2019-04-16 Gilead Sciences, Inc. 2-(N-pyrazolo)adenosines with application as adenosine A2A 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
US6605597B1 (en) * 1999-12-03 2003-08-12 Cv Therapeutics, Inc. Partial or full A1agonists-N-6 heterocyclic 5′-thio substituted adenosine derivatives
WO2001062979A2 (en) 2000-02-23 2001-08-30 Cv Therapeutics, Inc. Dentification of partial agonists of the a2a adenosine receptor
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
US6946449B2 (en) * 2001-07-13 2005-09-20 Cv Therapeutics, Inc. Partial and full agonists of A1 adenosine receptors
US7157440B2 (en) 2001-07-13 2007-01-02 Cv Therapeutics, Inc. Partial and full agonists of A1 adenosine receptors
US7713946B2 (en) 2002-07-11 2010-05-11 Cv Therapeutics, Inc. Partial and full agonists A1 adenosine receptors
JP2005527502A (ja) * 2002-02-19 2005-09-15 シーブイ・セラピューティクス・インコーポレイテッド Ａ１アデノシン受容体の部分的および全アゴニスト
JP2005530736A (ja) * 2002-04-18 2005-10-13 シーブイ・セラピューティクス・インコーポレイテッド ベーターブロッカー、カルシウムチャネルブロッカー、または心臓のグリコシドと共にａ１アデノシンアゴニストを投与することを含む不整脈の処置方法
US20050020915A1 (en) * 2002-07-29 2005-01-27 Cv Therapeutics, Inc. Myocardial perfusion imaging methods and compositions
US8470801B2 (en) 2002-07-29 2013-06-25 Gilead Sciences, 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
AU2004209986C1 (en) 2003-02-03 2009-08-13 Gilead Palo Alto, Inc. Partial and full agonists of A1 adenosine receptors
US7335648B2 (en) 2003-10-21 2008-02-26 Inspire Pharmaceuticals, Inc. Non-nucleotide composition and method for inhibiting platelet aggregation
US7749981B2 (en) 2003-10-21 2010-07-06 Inspire Pharmaceuticals, Inc. Drug-eluting stents coated with non-nucleotide P2Y12 receptor antagonist compound
JP2007509180A (ja) 2003-10-21 2007-04-12 インスパイアー ファーマシューティカルズ，インコーポレイティド 疼痛を治療するための、非ヌクレオチド組成物および方法
JP2007514647A (ja) 2003-10-21 2007-06-07 インスパイアー ファーマシューティカルズ，インコーポレイティド テトラヒドロ−フロ［３，４−ｄ］ジオキソール化合物並びに血小板凝集を阻害する組成物及び方法
ES2383525T3 (es) * 2003-11-05 2012-06-21 Sarcode Bioscience Inc. Moduladores de la adhesión celular
EP1802317A2 (en) 2004-10-20 2007-07-04 Cv Therapeutics, Inc. Use of a2a adenosine receptor agonists
US7932376B2 (en) 2005-05-05 2011-04-26 Inspire Pharmaceuticals, Inc. Pyrimidine-based non-nucleotide composition and method for inhibiting platelet aggregation
CA2609053C (en) 2005-05-17 2017-04-25 Sarcode Corporation Compositions and methods for treatment of eye disorders
CN101321460A (zh) * 2005-11-30 2008-12-10 伊诺泰克制药公司 嘌呤衍生物及其用法
AU2007212542B2 (en) 2006-02-03 2013-01-31 Gilead Sciences, Inc. Process for preparing an A2A-Adenosine receptor agonist and its polymorphs
EP2021350B1 (en) 2006-03-21 2016-12-21 Rheinische Friedrich-Wilhelms-Universität Bonn Phosphorylated a2a receptor agonists
EP2068850A1 (en) * 2006-06-22 2009-06-17 Cv Therapeutics, Inc. Use of a2a adenosine receptor agonists in the treatment of ischemia
US20090081120A1 (en) * 2006-09-01 2009-03-26 Cv Therapeutics, Inc. Methods and Compositions for Increasing Patient Tolerability During Myocardial Imaging Methods
MX2009002299A (es) * 2006-09-01 2009-03-20 Cv Therapeutics Inc Metodos y composiciones para incrementar la tolerancia del paciente durante metodos de formacion de imagenes del miocardio.
EP2066232A1 (en) * 2006-09-29 2009-06-10 Cv Therapeutics, Inc. Methods for myocardial imaging in patients having a history of pulmonary disease
WO2008086096A2 (en) * 2007-01-03 2008-07-17 Cv Therapeutics, Inc. Myocardial perfusion imaging
EP3797775A1 (en) 2007-10-19 2021-03-31 Novartis AG Compositions and methods for treatment of diabetic retinopathy
US20110064671A1 (en) 2008-03-10 2011-03-17 Cornell University Modulation of blood brain barrier permeability
CN102065893A (zh) * 2008-04-15 2011-05-18 萨可德公司 Lfa-1拮抗剂向胃肠系统的递送
WO2009139817A2 (en) 2008-04-15 2009-11-19 Sarcode Corporation Crystalline pharmaceutical and methods of preparation and use thereof
JP2011518155A (ja) * 2008-04-15 2011-06-23 サーコード コーポレイション 免疫関連障害の局所治療に使用するためのエアゾール化ｌｆａ−１アンタゴニスト
ES2763703T3 (es) * 2008-04-15 2020-05-29 Sarcode Bioscience Inc Antagonistas de LFA-1 tópicos utilizados en el tratamiento localizado de trastornos inmunes
US20100086483A1 (en) * 2008-09-29 2010-04-08 Gilead Palo Alto, Inc. Method of multidetector computed tomagraphy
US8378105B2 (en) * 2009-10-21 2013-02-19 Sarcode Bioscience Inc. Crystalline pharmaceutical and methods of preparation and use thereof
CN101934559B (zh) * 2010-08-12 2013-04-17 中国电子科技集团公司第四十五研究所 具有压力调节机构的砂浆供给装置
MX2015001098A (es) 2012-07-25 2015-09-25 Sarcode Bioscience Inc Inhibidor del antigeno-1 asociado a la funcion del linfocito (lfa-1) y polimorfo del mismo.

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4373097A (en) 1981-04-27 1983-02-08 Bioresearch S.R.L. Process for preparing adenosine derivatives of anti-inflammatory and analgesic activity
US5589467A (en) 1993-09-17 1996-12-31 Novo Nordisk A/S 2,5',N6-trisubstituted adenosine derivatives
KR100254106B1 (ko) * 1994-06-09 2000-05-01 타이도 나오카타 4-퀴놀리논 유도체 또는 그의 염
US5789416B1 (en) * 1996-08-27 1999-10-05 Cv Therapeutics Inc N6 mono heterocyclic substituted adenosine derivatives
GB9723566D0 (en) * 1997-11-08 1998-01-07 Glaxo Group Ltd Chemical compounds
GB9723590D0 (en) * 1997-11-08 1998-01-07 Glaxo Group Ltd Chemical compounds
US6294522B1 (en) * 1999-12-03 2001-09-25 Cv Therapeutics, Inc. N6 heterocyclic 8-modified adenosine derivatives
US6258793B1 (en) * 1999-12-03 2001-07-10 Cv Therapeutics, Inc. N6 heterocyclic 5′ 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

Also Published As

Publication number Publication date
IL145903A (en) 2006-04-10
KR20030032907A (ko) 2003-04-26
CA2389264C (en) 2007-03-06
CN1378550A (zh) 2002-11-06
CN1152042C (zh) 2004-06-02
WO2001040243A2 (en) 2001-06-07
AU7938301A (en) 2002-03-21
JP2003516325A (ja) 2003-05-13
BR0016126A (pt) 2002-08-06
ATE254133T1 (de) 2003-11-15
US6605597B1 (en) 2003-08-12
NO20015373L (no) 2001-11-29
NO20015373D0 (no) 2001-11-02
AU1811701A (en) 2001-06-12
AU761029B2 (en) 2003-05-29
US20050054605A1 (en) 2005-03-10
TR200301971T4 (tr) 2004-01-21
TWI249536B (en) 2006-02-21
DE60006576D1 (de) 2003-12-18
ZA200204380B (en) 2003-06-25
TR200103129T2 (tr) 2002-10-21
MXPA01011113A (es) 2002-06-04
EP1233973B1 (en) 2003-11-12
KR100484988B1 (ko) 2005-04-22
CA2389264A1 (en) 2001-06-07
CZ20013705A3 (cs) 2002-04-17
JP4021195B2 (ja) 2007-12-12
AR029199A1 (es) 2003-06-18
AU4138701A (en) 2001-06-12
HK1047941A1 (zh) 2003-03-14
PT1233973E (pt) 2004-02-27
DK1233973T3 (da) 2004-02-16
NZ514777A (en) 2004-01-30
WO2001040243A3 (en) 2001-12-13
ES2208437T3 (es) 2004-06-16
DE60006576T2 (de) 2004-09-16
WO2001040246A1 (en) 2001-06-07
EP1233973A1 (en) 2002-08-28

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