JP4357960B2 - アデノシンａ３レセプターアゴニスト - Google Patents
アデノシンａ３レセプターアゴニスト Download PDFInfo
- Publication number
- JP4357960B2 JP4357960B2 JP2003519086A JP2003519086A JP4357960B2 JP 4357960 B2 JP4357960 B2 JP 4357960B2 JP 2003519086 A JP2003519086 A JP 2003519086A JP 2003519086 A JP2003519086 A JP 2003519086A JP 4357960 B2 JP4357960 B2 JP 4357960B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- hydroxymethyl
- diol
- oxolane
- purin
- 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
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- 239000002593 adenosine A3 receptor agonist Substances 0.000 title description 4
- 229940122216 Adenosine A3 receptor agonist Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 159
- -1 4- (4-methoxyphenyl) pyrazol-1-yl Chemical group 0.000 claims description 88
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 42
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 34
- 125000004545 purin-9-yl group Chemical group N1=CN=C2N(C=NC2=C1)* 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 7
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
- TVDMIJMDRGHRAP-VZKMNXCRSA-N (2r,3s,4r,5r)-2-(hydroxymethyl)-5-[2-[4-(4-methoxyphenyl)-1h-pyrazol-5-yl]-6-(propylamino)purin-9-yl]oxolane-3,4-diol Chemical compound C1=NC=2C(NCCC)=NC(C=3C(=CNN=3)C=3C=CC(OC)=CC=3)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O TVDMIJMDRGHRAP-VZKMNXCRSA-N 0.000 claims description 3
- BWDVNCCNAFMZAY-KHTYJDQRSA-N C1=NC=2C(NC)=NC(N3N=CC(=C3)C(=O)NC=3C=CC(Cl)=CC=3)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O Chemical compound C1=NC=2C(NC)=NC(N3N=CC(=C3)C(=O)NC=3C=CC(Cl)=CC=3)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O BWDVNCCNAFMZAY-KHTYJDQRSA-N 0.000 claims description 2
- KOMMANOLQOQETJ-VGKBRBPRSA-N (2r,3r,4s,5r)-2-[2-(1-benzylpyrazol-3-yl)-6-(methylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C1=NC=2C(NC)=NC(C3=NN(CC=4C=CC=CC=4)C=C3)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O KOMMANOLQOQETJ-VGKBRBPRSA-N 0.000 claims 1
- SFQRNHJUCJDFMN-DYVMYPEFSA-N (2r,3r,4s,5r)-2-[2-(1-benzylpyrazol-3-yl)-6-(propylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C1=NC=2C(NCCC)=NC(C3=NN(CC=4C=CC=CC=4)C=C3)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O SFQRNHJUCJDFMN-DYVMYPEFSA-N 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- NVYOVCWFMVMAKW-VGKBRBPRSA-N n-[(4-chlorophenyl)methyl]-1-[9-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-(methylamino)purin-2-yl]pyrazole-4-carboxamide Chemical compound C1=NC=2C(NC)=NC(N3N=CC(=C3)C(=O)NCC=3C=CC(Cl)=CC=3)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O NVYOVCWFMVMAKW-VGKBRBPRSA-N 0.000 claims 1
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- 125000000217 alkyl group Chemical group 0.000 description 67
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- 238000006243 chemical reaction Methods 0.000 description 27
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- 125000000623 heterocyclic group Chemical group 0.000 description 23
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 21
- 125000004432 carbon atom Chemical group C* 0.000 description 20
- 125000004181 carboxyalkyl group Chemical group 0.000 description 20
- 125000000753 cycloalkyl group Chemical group 0.000 description 20
- 238000002360 preparation method Methods 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000004480 active ingredient Substances 0.000 description 18
- 125000003342 alkenyl group Chemical group 0.000 description 18
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- 125000000392 cycloalkenyl group Chemical group 0.000 description 17
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- 125000003107 substituted aryl group Chemical group 0.000 description 11
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- 125000004414 alkyl thio group Chemical group 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- 230000002829 reductive effect Effects 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 229930194542 Keto Natural products 0.000 description 9
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- 125000002252 acyl group Chemical group 0.000 description 9
- 125000004442 acylamino group Chemical group 0.000 description 9
- 125000004423 acyloxy group Chemical group 0.000 description 9
- 125000005110 aryl thio group Chemical group 0.000 description 9
- 125000004104 aryloxy group Chemical group 0.000 description 9
- 125000005553 heteroaryloxy group Chemical group 0.000 description 9
- 125000000468 ketone group Chemical group 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 239000000546 pharmaceutical excipient Substances 0.000 description 9
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 description 9
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 9
- 150000003573 thiols Chemical class 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 125000000033 alkoxyamino group Chemical group 0.000 description 8
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 8
- 125000006598 aminocarbonylamino group Chemical group 0.000 description 8
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 125000005368 heteroarylthio group Chemical group 0.000 description 8
- 125000004468 heterocyclylthio group Chemical group 0.000 description 8
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 8
- 229940044601 receptor agonist Drugs 0.000 description 8
- 239000000018 receptor agonist Substances 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 150000001540 azides Chemical class 0.000 description 7
- 125000004470 heterocyclooxy group Chemical group 0.000 description 7
- 150000002431 hydrogen Chemical class 0.000 description 7
- 239000008194 pharmaceutical composition Substances 0.000 description 7
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- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 6
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
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- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 4
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- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
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Classifications
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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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Reproductive Health (AREA)
- Cardiology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31106901P | 2001-08-08 | 2001-08-08 | |
| PCT/US2002/024696 WO2003014137A1 (en) | 2001-08-08 | 2002-08-06 | Adenosine a3 receptor agonists |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005501842A JP2005501842A (ja) | 2005-01-20 |
| JP2005501842A5 JP2005501842A5 (https=) | 2005-11-17 |
| JP4357960B2 true JP4357960B2 (ja) | 2009-11-04 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| JP2003519086A Expired - Fee Related JP4357960B2 (ja) | 2001-08-08 | 2002-08-06 | アデノシンａ３レセプターアゴニスト |
Country Status (20)
| Country | Link |
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| US (1) | US20030078232A1 (https=) |
| EP (1) | EP1414837B1 (https=) |
| JP (1) | JP4357960B2 (https=) |
| KR (1) | KR100923888B1 (https=) |
| CN (1) | CN1244589C (https=) |
| AT (1) | ATE307136T1 (https=) |
| AU (1) | AU2002327426C1 (https=) |
| CA (1) | CA2456744A1 (https=) |
| DE (1) | DE60206775T2 (https=) |
| DK (1) | DK1414837T3 (https=) |
| ES (1) | ES2247371T3 (https=) |
| HU (1) | HUP0401437A3 (https=) |
| IL (2) | IL160231A0 (https=) |
| MX (1) | MXPA04001185A (https=) |
| NO (1) | NO327997B1 (https=) |
| NZ (1) | NZ530976A (https=) |
| PL (1) | PL368205A1 (https=) |
| RU (1) | RU2298557C2 (https=) |
| WO (1) | WO2003014137A1 (https=) |
| ZA (1) | ZA200401000B (https=) |
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| US7427606B2 (en) | 1999-02-01 | 2008-09-23 | University Of Virginia Patent Foundation | Method to reduce inflammatory response in transplanted tissue |
| US7378400B2 (en) | 1999-02-01 | 2008-05-27 | University Of Virginia Patent Foundation | Method to reduce an inflammatory response from arthritis |
| US6232297B1 (en) | 1999-02-01 | 2001-05-15 | University Of Virginia Patent Foundation | Methods and compositions for treating inflammatory response |
| US7074801B1 (en) * | 2001-04-26 | 2006-07-11 | Eisai Co., Ltd. | Nitrogen-containing condensed cyclic compound having a pyrazolyl group as a substituent group and pharmaceutical composition thereof |
| NZ556354A (en) | 2001-10-01 | 2008-10-31 | Univ Virginia | 2-Propynyl adenosine analogs having A2A agonist activity and compositions thereof |
| US6914053B2 (en) * | 2002-09-09 | 2005-07-05 | Cv Therapeutics, Inc. | Adenosine A3 receptor agonists |
| WO2004086034A2 (en) * | 2003-03-28 | 2004-10-07 | Bayer Healthcare Ag | Diagnostics and therapeutics for diseases associated with g-protein-coupled receptor adenosine a3(adora3) |
| CA2532965C (en) | 2003-07-22 | 2013-05-14 | Astex Therapeutics Limited | 3, 4-disubstituted 1h-pyrazole compounds and their use as cyclin dependent kinases (cdk) and glycogen synthase kinase-3 (gsk-3) modulators |
| PE20060272A1 (es) | 2004-05-24 | 2006-05-22 | Glaxo Group Ltd | (2r,3r,4s,5r,2'r,3'r,4's,5's)-2,2'-{trans-1,4-ciclohexanodiilbis-[imino(2-{[2-(1-metil-1h-imidazol-4-il)etil]amino}-9h-purin-6,9-diil)]}bis[5-(2-etil-2h-tetrazol-5-il)tetrahidro-3,4-furanodiol] como agonista a2a |
| AU2005267706B2 (en) | 2004-08-02 | 2011-12-08 | University Of Virginia Patent Foundation | 2-propynyl adenosine analogs with modified 5'-ribose groups having A2A agonist activity |
| US7576069B2 (en) | 2004-08-02 | 2009-08-18 | University Of Virginia Patent Foundation | 2-polycyclic propynyl adenosine analogs 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 |
| CA2585581A1 (en) * | 2004-11-22 | 2006-05-26 | King Pharmaceuticals Research & Development Inc. | Enhancing treatment of hif-1 mediated disorders with adenosine a3 receptor agonists |
| MX2007008781A (es) | 2005-01-21 | 2007-09-11 | Astex Therapeutics Ltd | Compuestos farmaceuticos. |
| GB0505219D0 (en) * | 2005-03-14 | 2005-04-20 | Novartis Ag | Organic compounds |
| JP5042996B2 (ja) * | 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アデノシンレセプターアゴニスト |
| US7514417B2 (en) | 2005-05-19 | 2009-04-07 | Cv Therapeutics, Inc. | A1 adenosine receptor agonists |
| GB0514809D0 (en) | 2005-07-19 | 2005-08-24 | Glaxo Group Ltd | Compounds |
| ATE497960T1 (de) * | 2005-10-13 | 2011-02-15 | Cv Therapeutics Inc | A1-adenosinrezeptoragonisten |
| US8178509B2 (en) | 2006-02-10 | 2012-05-15 | University Of Virginia Patent Foundation | Method to treat sickle cell disease |
| US7589076B2 (en) * | 2006-05-18 | 2009-09-15 | Pgx Health, Llc | Substituted aryl piperidinylalkynyladenosines as A2AR agonists |
| US8188063B2 (en) | 2006-06-19 | 2012-05-29 | University Of Virginia Patent Foundation | Use of adenosine A2A modulators to treat spinal cord injury |
| DE102007012645A1 (de) * | 2007-03-16 | 2008-09-18 | Bayer Healthcare Ag | Substituierte Imidazo- und Triazolopyrimidine |
| EP2144911A2 (en) | 2007-03-28 | 2010-01-20 | NeuroSearch AS | Purinyl derivatives and their use as potassium channel modulators |
| KR101564233B1 (ko) * | 2007-03-28 | 2015-10-29 | 뉴로서치 에이/에스 | 푸리닐 유도체 및 칼륨 채널 조절제로서의 이의 용도 |
| US20090088403A1 (en) * | 2007-05-07 | 2009-04-02 | Randy Blakely | A3 adenosine receptors as targets for the modulation of central serotonergic signaling |
| WO2009052310A1 (en) * | 2007-10-16 | 2009-04-23 | Cv Therapeutics, Inc | A3 adenosine receptor antagonists |
| 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 |
| RU2451010C1 (ru) * | 2011-01-11 | 2012-05-20 | Закрытое Акционерное Общество "Ива Фарм" | Палладиево-медные катализаторы гомогенного селективного окисления тиольных групп, комбинация и композиция на их основе и способ терапевтического воздействия |
| US9475797B2 (en) | 2012-06-26 | 2016-10-25 | Saniona A/S | Phenyl triazole derivative and its use for modulating the GABAA receptor complex |
| WO2014138485A1 (en) * | 2013-03-08 | 2014-09-12 | Irm Llc | Ex vivo production of platelets from hematopoietic stem cells and the product thereof |
| CN110545822A (zh) | 2017-05-19 | 2019-12-06 | 全技术公司 | 药剂、组合物及其相关方法 |
| CN113795267A (zh) | 2019-03-12 | 2021-12-14 | 艾库斯生物科学有限公司 | 致癌基因驱动的癌症的治疗 |
| WO2020205527A1 (en) | 2019-03-29 | 2020-10-08 | Arcus Biosciences, Inc. | Treatment of cancer utilizing an identified adenosine fingerprint |
| JP2022538409A (ja) * | 2019-06-21 | 2022-09-02 | アカデミー オブ ミリタリー メディカル サイエンシズ | アデノシン化合物、その医薬的に許容可能な塩又はその立体異性体及びその使用 |
| AU2021413448A1 (en) * | 2020-12-29 | 2023-07-20 | Zhejiang Vimgreen Pharmaceuticals, Ltd | Adenosine a3 receptor agonists, preparation methods and uses thereof |
Family Cites Families (3)
| 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 |
| US6180615B1 (en) * | 1999-06-22 | 2001-01-30 | Cv Therapeutics, Inc. | Propargyl phenyl ether A2A receptor agonists |
| US6403567B1 (en) * | 1999-06-22 | 2002-06-11 | Cv Therapeutics, Inc. | N-pyrazole A2A adenosine receptor agonists |
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2002
- 2002-08-05 US US10/212,896 patent/US20030078232A1/en not_active Abandoned
- 2002-08-06 AU AU2002327426A patent/AU2002327426C1/en not_active Ceased
- 2002-08-06 NZ NZ530976A patent/NZ530976A/en not_active IP Right Cessation
- 2002-08-06 ES ES02763415T patent/ES2247371T3/es not_active Expired - Lifetime
- 2002-08-06 IL IL16023102A patent/IL160231A0/xx unknown
- 2002-08-06 CA CA002456744A patent/CA2456744A1/en not_active Abandoned
- 2002-08-06 DE DE60206775T patent/DE60206775T2/de not_active Expired - Lifetime
- 2002-08-06 EP EP02763415A patent/EP1414837B1/en not_active Expired - Lifetime
- 2002-08-06 HU HU0401437A patent/HUP0401437A3/hu unknown
- 2002-08-06 MX MXPA04001185A patent/MXPA04001185A/es active IP Right Grant
- 2002-08-06 AT AT02763415T patent/ATE307136T1/de not_active IP Right Cessation
- 2002-08-06 RU RU2004106635/04A patent/RU2298557C2/ru not_active IP Right Cessation
- 2002-08-06 KR KR1020047001949A patent/KR100923888B1/ko not_active Expired - Fee Related
- 2002-08-06 JP JP2003519086A patent/JP4357960B2/ja not_active Expired - Fee Related
- 2002-08-06 CN CNB02815486XA patent/CN1244589C/zh not_active Expired - Fee Related
- 2002-08-06 PL PL02368205A patent/PL368205A1/xx not_active Application Discontinuation
- 2002-08-06 DK DK02763415T patent/DK1414837T3/da active
- 2002-08-06 WO PCT/US2002/024696 patent/WO2003014137A1/en not_active Ceased
-
2004
- 2004-02-05 IL IL160231A patent/IL160231A/en not_active IP Right Cessation
- 2004-02-06 ZA ZA200401000A patent/ZA200401000B/en unknown
- 2004-03-05 NO NO20040969A patent/NO327997B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AU2002327426B2 (en) | 2007-06-14 |
| NO20040969L (no) | 2004-04-19 |
| MXPA04001185A (es) | 2005-06-17 |
| KR20040023733A (ko) | 2004-03-18 |
| JP2005501842A (ja) | 2005-01-20 |
| WO2003014137A1 (en) | 2003-02-20 |
| US20030078232A1 (en) | 2003-04-24 |
| RU2004106635A (ru) | 2005-07-27 |
| DE60206775T2 (de) | 2006-07-20 |
| AU2002327426A2 (en) | 2003-02-24 |
| PL368205A1 (en) | 2005-03-21 |
| HUP0401437A3 (en) | 2007-05-29 |
| AU2002327426C1 (en) | 2008-03-06 |
| NO327997B1 (no) | 2009-11-09 |
| EP1414837A1 (en) | 2004-05-06 |
| RU2298557C2 (ru) | 2007-05-10 |
| DE60206775D1 (de) | 2006-03-02 |
| EP1414837B1 (en) | 2005-10-19 |
| HUP0401437A2 (hu) | 2004-11-29 |
| CN1538972A (zh) | 2004-10-20 |
| NZ530976A (en) | 2005-07-29 |
| IL160231A0 (en) | 2004-07-25 |
| ES2247371T3 (es) | 2006-03-01 |
| ZA200401000B (en) | 2004-10-18 |
| ATE307136T1 (de) | 2005-11-15 |
| CN1244589C (zh) | 2006-03-08 |
| KR100923888B1 (ko) | 2009-10-28 |
| CA2456744A1 (en) | 2003-02-20 |
| DK1414837T3 (da) | 2005-11-07 |
| IL160231A (en) | 2010-11-30 |
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