ES2288632T3 - Agonistas parciales y completos de los receptores a1 adenosina a1. - Google Patents
Agonistas parciales y completos de los receptores a1 adenosina a1. Download PDFInfo
- Publication number
- ES2288632T3 ES2288632T3 ES03788541T ES03788541T ES2288632T3 ES 2288632 T3 ES2288632 T3 ES 2288632T3 ES 03788541 T ES03788541 T ES 03788541T ES 03788541 T ES03788541 T ES 03788541T ES 2288632 T3 ES2288632 T3 ES 2288632T3
- Authority
- ES
- Spain
- Prior art keywords
- purin
- formula
- optionally substituted
- diol
- oxolane
- 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 - Lifetime
Links
- 239000000556 agonist Substances 0.000 title description 41
- 230000036961 partial effect Effects 0.000 title description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 74
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 74
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 64
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 57
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 37
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 35
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 27
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 26
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 20
- 125000002252 acyl group Chemical group 0.000 claims abstract description 12
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 12
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims abstract description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 7
- 150000002431 hydrogen Chemical class 0.000 claims abstract 3
- 125000001475 halogen functional group Chemical group 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 318
- -1 2-trifluoromethylphenyl Chemical group 0.000 claims description 170
- 238000002360 preparation method Methods 0.000 claims description 107
- 239000000203 mixture Substances 0.000 claims description 74
- 125000004545 purin-9-yl group Chemical group N1=CN=C2N(C=NC2=C1)* 0.000 claims description 56
- 125000003118 aryl group Chemical group 0.000 claims description 47
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 44
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 38
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 34
- 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 claims description 28
- 230000000694 effects Effects 0.000 claims description 24
- 125000006312 cyclopentyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 23
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 201000010099 disease Diseases 0.000 claims description 17
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 15
- 239000002126 C01EB10 - Adenosine Substances 0.000 claims description 14
- 229960005305 adenosine Drugs 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 12
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- 230000003243 anti-lipolytic effect Effects 0.000 claims description 10
- LRBPVCVOHOVJOV-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-(cyclopentylamino)purin-9-yl]-5-[2-(2-fluorophenyl)ethynyl]oxolane-3,4-diol Chemical compound C([C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C2=NC=NC(NC3CCCC3)=C2N=C1)#CC1=CC=CC=C1F LRBPVCVOHOVJOV-WGQQHEPDSA-N 0.000 claims description 8
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- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 6
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- 208000008589 Obesity Diseases 0.000 claims description 5
- 208000003734 Supraventricular Tachycardia Diseases 0.000 claims description 5
- 208000028867 ischemia Diseases 0.000 claims description 5
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 5
- 235000020824 obesity Nutrition 0.000 claims description 5
- 208000030159 metabolic disease Diseases 0.000 claims description 4
- FZOKRCLVLPATSB-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-(cyclopentylamino)purin-9-yl]-5-(2-phenylethenyl)oxolane-3,4-diol Chemical compound N1=CN=C2N([C@@H]3O[C@@H]([C@H]([C@H]3O)O)C=CC=3C=CC=CC=3)C=NC2=C1NC1CCCC1 FZOKRCLVLPATSB-WGQQHEPDSA-N 0.000 claims description 3
- WDASMIRQGXPOGJ-ZDXOVATRSA-N (2r,3r,4s,5r)-2-[6-(cyclopentylamino)purin-9-yl]-5-[2-(2-methylphenyl)ethenyl]oxolane-3,4-diol Chemical compound CC1=CC=CC=C1C=C[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C3=NC=NC(NC4CCCC4)=C3N=C2)O1 WDASMIRQGXPOGJ-ZDXOVATRSA-N 0.000 claims description 3
- 206010003658 Atrial Fibrillation Diseases 0.000 claims description 3
- 206010003662 Atrial flutter Diseases 0.000 claims description 3
- 102000004877 Insulin Human genes 0.000 claims description 3
- 108090001061 Insulin Proteins 0.000 claims description 3
- 230000001419 dependent effect Effects 0.000 claims description 3
- 229940125396 insulin Drugs 0.000 claims description 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 2
- 208000007718 Stable Angina Diseases 0.000 claims description 2
- 208000006011 Stroke Diseases 0.000 claims description 2
- 208000010125 myocardial infarction Diseases 0.000 claims description 2
- 229940044601 receptor agonist Drugs 0.000 claims description 2
- 239000000018 receptor agonist Substances 0.000 claims description 2
- 206010002388 Angina unstable Diseases 0.000 claims 1
- 239000003379 purinergic P1 receptor agonist Substances 0.000 abstract description 5
- 238000006243 chemical reaction Methods 0.000 description 67
- 238000000034 method Methods 0.000 description 46
- 125000001424 substituent group Chemical group 0.000 description 46
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 46
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 43
- 229920002554 vinyl polymer Polymers 0.000 description 43
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
- 239000002904 solvent Substances 0.000 description 42
- 239000000243 solution Substances 0.000 description 41
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 34
- 230000002829 reductive effect Effects 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- 125000003545 alkoxy group Chemical group 0.000 description 26
- 229910052736 halogen Inorganic materials 0.000 description 26
- 150000002367 halogens Chemical class 0.000 description 26
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 24
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 125000003342 alkenyl group Chemical group 0.000 description 20
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 20
- 239000002253 acid Substances 0.000 description 18
- 125000004542 purin-6-yl group Chemical group N1=CN=C2N=CNC2=C1* 0.000 description 18
- 239000003826 tablet Substances 0.000 description 18
- 150000001412 amines Chemical class 0.000 description 17
- 125000000392 cycloalkenyl group Chemical group 0.000 description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
- 239000004480 active ingredient Substances 0.000 description 16
- 125000000304 alkynyl group Chemical group 0.000 description 16
- 210000004027 cell Anatomy 0.000 description 16
- 235000019439 ethyl acetate Nutrition 0.000 description 15
- 235000021588 free fatty acids Nutrition 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- 241000700159 Rattus Species 0.000 description 14
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 13
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- 238000007796 conventional method Methods 0.000 description 13
- 238000002474 experimental method Methods 0.000 description 13
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- 150000005830 nonesterified fatty acids Chemical class 0.000 description 13
- 239000000725 suspension Substances 0.000 description 13
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- 206010047700 Vomiting Diseases 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
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- 102000005962 receptors Human genes 0.000 description 12
- 108020003175 receptors Proteins 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- 230000014509 gene expression Effects 0.000 description 11
- 101150007969 ADORA1 gene Proteins 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 210000001789 adipocyte Anatomy 0.000 description 10
- 125000004414 alkyl thio group Chemical group 0.000 description 10
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- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 10
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- FFBDFADSZUINTG-UHFFFAOYSA-N DPCPX Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C1CCCC1 FFBDFADSZUINTG-UHFFFAOYSA-N 0.000 description 9
- 229930194542 Keto Natural products 0.000 description 9
- 125000004442 acylamino group Chemical group 0.000 description 9
- 125000004423 acyloxy group Chemical group 0.000 description 9
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- SQMWSBKSHWARHU-SDBHATRESA-N n6-cyclopentyladenosine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC=NC(NC3CCCC3)=C2N=C1 SQMWSBKSHWARHU-SDBHATRESA-N 0.000 description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 8
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- ZJZMIZHGAMSAEG-SCFUHWHPSA-N 9-[(3ar,4r,6r,6ar)-6-ethynyl-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-n-cyclopentylpurin-6-amine Chemical compound N1=CN=C2N([C@@H]3O[C@@H]([C@H]4OC(O[C@H]43)(C)C)C#C)C=NC2=C1NC1CCCC1 ZJZMIZHGAMSAEG-SCFUHWHPSA-N 0.000 description 5
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
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- 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
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- 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
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
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- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
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- 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
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- 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
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- 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
- A61P9/06—Antiarrhythmics
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- 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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- 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
Landscapes
- 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)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Diabetes (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Immunology (AREA)
- Hematology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Obesity (AREA)
- Emergency Medicine (AREA)
- Vascular Medicine (AREA)
- Transplantation (AREA)
- Endocrinology (AREA)
- Urology & Nephrology (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40371202P | 2002-08-15 | 2002-08-15 | |
| US403712P | 2002-08-15 | ||
| US45009403P | 2003-02-25 | 2003-02-25 | |
| US450094P | 2003-02-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2288632T3 true ES2288632T3 (es) | 2008-01-16 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES03788541T Expired - Lifetime ES2288632T3 (es) | 2002-08-15 | 2003-08-15 | Agonistas parciales y completos de los receptores a1 adenosina a1. |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US7022681B2 (https=) |
| EP (1) | EP1537133B1 (https=) |
| JP (1) | JP4596913B2 (https=) |
| KR (1) | KR20050067384A (https=) |
| CN (1) | CN100480255C (https=) |
| AT (1) | ATE368048T1 (https=) |
| AU (1) | AU2003263846B2 (https=) |
| CA (1) | CA2495370A1 (https=) |
| DE (1) | DE60315164T2 (https=) |
| ES (1) | ES2288632T3 (https=) |
| MX (1) | MXPA05001844A (https=) |
| NO (1) | NO20051296L (https=) |
| NZ (1) | NZ538590A (https=) |
| RU (1) | RU2340623C2 (https=) |
| WO (1) | WO2004016635A2 (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2528385C (en) | 2003-06-06 | 2011-03-15 | Endacea, Inc. | A1 adenosine receptor antogonists |
| WO2008143667A1 (en) * | 2007-05-17 | 2008-11-27 | Cv Therapeutics, Inc. | Process for preparing an a2a-adenosine receptor agonist and its polymorphs |
| JP2014530910A (ja) * | 2011-10-24 | 2014-11-20 | グラクソスミスクライン、インテレクチュアル、プロパティー、ナンバー２、リミテッドＧｌａｘｏｓｍｉｔｈｋｌｉｎｅ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ Ｎｏ．２ Ｌｉｍｉｔｅｄ | 新規化合物 |
| JP6584521B2 (ja) * | 2015-02-24 | 2019-10-02 | ファイザー・インク | 抗がん剤として有用な置換ヌクレオシド誘導体 |
| JP6643719B2 (ja) * | 2016-05-31 | 2020-02-12 | セントラル硝子株式会社 | ３，３，３−トリフルオロプロパノールの製造方法 |
Family Cites Families (11)
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|---|---|---|---|---|
| CA1254888A (en) * | 1984-10-26 | 1989-05-30 | Bharat Trivedi | N.sup.6-bicycloadenosines |
| USRE36494E (en) * | 1990-02-20 | 2000-01-11 | Discovery Therapeutics, Inc. | 2-aralkoxy and 2-alkoxy adenosine derivatives as coronary vasodilators and antihypertensive agents |
| US5140015A (en) * | 1990-02-20 | 1992-08-18 | Whitby Research, Inc. | 2-aralkoxy and 2-alkoxy adenosine derivatives as coronary vasodilators and antihypertensive agents |
| US5278150A (en) * | 1992-04-24 | 1994-01-11 | Whitby Research, Inc. | 2-hydrazoadenosines and their utility for the treatmeat of vascular conditions |
| GB9301000D0 (en) * | 1993-01-20 | 1993-03-10 | Glaxo Group Ltd | Chemical compounds |
| US5589467A (en) * | 1993-09-17 | 1996-12-31 | Novo Nordisk A/S | 2,5',N6-trisubstituted adenosine derivatives |
| WO1997033591A1 (en) * | 1996-03-13 | 1997-09-18 | Novo Nordisk A/S | A method of treating disorders related to cytokines in mammals |
| WO1998016539A1 (en) * | 1996-10-14 | 1998-04-23 | Novo Nordisk A/S | Novel therapeutically active adenosine derivatives |
| GB9723589D0 (en) * | 1997-11-08 | 1998-01-07 | Glaxo Group Ltd | Chemical compounds |
| GB9813554D0 (en) * | 1998-06-23 | 1998-08-19 | Glaxo Group Ltd | Chemical compounds |
| US20040162422A1 (en) * | 2001-03-20 | 2004-08-19 | Adrian Hall | Chemical compounds |
-
2003
- 2003-08-15 JP JP2004529472A patent/JP4596913B2/ja not_active Expired - Fee Related
- 2003-08-15 US US10/641,930 patent/US7022681B2/en not_active Expired - Fee Related
- 2003-08-15 AU AU2003263846A patent/AU2003263846B2/en not_active Ceased
- 2003-08-15 WO PCT/US2003/025629 patent/WO2004016635A2/en not_active Ceased
- 2003-08-15 RU RU2005106997/04A patent/RU2340623C2/ru not_active IP Right Cessation
- 2003-08-15 NZ NZ538590A patent/NZ538590A/en not_active IP Right Cessation
- 2003-08-15 MX MXPA05001844A patent/MXPA05001844A/es active IP Right Grant
- 2003-08-15 EP EP03788541A patent/EP1537133B1/en not_active Expired - Lifetime
- 2003-08-15 CA CA002495370A patent/CA2495370A1/en not_active Abandoned
- 2003-08-15 KR KR1020057002587A patent/KR20050067384A/ko not_active Ceased
- 2003-08-15 DE DE60315164T patent/DE60315164T2/de not_active Expired - Lifetime
- 2003-08-15 CN CNB038193612A patent/CN100480255C/zh not_active Expired - Fee Related
- 2003-08-15 ES ES03788541T patent/ES2288632T3/es not_active Expired - Lifetime
- 2003-08-15 AT AT03788541T patent/ATE368048T1/de not_active IP Right Cessation
-
2005
- 2005-03-14 NO NO20051296A patent/NO20051296L/no not_active Application Discontinuation
-
2006
- 2006-02-15 US US11/355,656 patent/US20060135467A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| NZ538590A (en) | 2006-10-27 |
| CN1675235A (zh) | 2005-09-28 |
| US7022681B2 (en) | 2006-04-04 |
| JP2006505525A (ja) | 2006-02-16 |
| US20060135467A1 (en) | 2006-06-22 |
| EP1537133A2 (en) | 2005-06-08 |
| CA2495370A1 (en) | 2004-02-26 |
| RU2340623C2 (ru) | 2008-12-10 |
| NO20051296L (no) | 2005-05-13 |
| AU2003263846B2 (en) | 2009-12-17 |
| KR20050067384A (ko) | 2005-07-01 |
| JP4596913B2 (ja) | 2010-12-15 |
| US20040043960A1 (en) | 2004-03-04 |
| MXPA05001844A (es) | 2005-04-19 |
| DE60315164T2 (de) | 2008-04-30 |
| RU2005106997A (ru) | 2005-11-10 |
| ATE368048T1 (de) | 2007-08-15 |
| DE60315164D1 (de) | 2007-09-06 |
| CN100480255C (zh) | 2009-04-22 |
| WO2004016635A3 (en) | 2004-04-08 |
| EP1537133B1 (en) | 2007-07-25 |
| AU2003263846A1 (en) | 2004-03-03 |
| WO2004016635A2 (en) | 2004-02-26 |
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