PH26672A - 2-(substituted amino) adenosines as antihypertensives - Google Patents
2-(substituted amino) adenosines as antihypertensives Download PDFInfo
- Publication number
- PH26672A PH26672A PH39015A PH39015A PH26672A PH 26672 A PH26672 A PH 26672A PH 39015 A PH39015 A PH 39015A PH 39015 A PH39015 A PH 39015A PH 26672 A PH26672 A PH 26672A
- Authority
- PH
- Philippines
- Prior art keywords
- lower alkyl
- hydrogen
- carboxy
- alkylene
- substituted
- Prior art date
Links
- -1 2-(substituted amino) adenosines Chemical class 0.000 title claims description 80
- 229940030600 antihypertensive agent Drugs 0.000 title description 2
- 239000002220 antihypertensive agent Substances 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 180
- 239000001257 hydrogen Substances 0.000 claims description 145
- 229910052739 hydrogen Inorganic materials 0.000 claims description 145
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 131
- 150000001875 compounds Chemical class 0.000 claims description 113
- 150000002148 esters Chemical class 0.000 claims description 85
- 150000003839 salts Chemical class 0.000 claims description 63
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 57
- 125000002947 alkylene group Chemical group 0.000 claims description 49
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 40
- 239000002126 C01EB10 - Adenosine Substances 0.000 claims description 35
- 229960005305 adenosine Drugs 0.000 claims description 35
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 35
- 229910052799 carbon Inorganic materials 0.000 claims description 32
- 125000003545 alkoxy group Chemical group 0.000 claims description 30
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 28
- 229910052736 halogen Inorganic materials 0.000 claims description 26
- 150000002367 halogens Chemical class 0.000 claims description 26
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 20
- 150000001408 amides Chemical class 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 16
- 241000124008 Mammalia Species 0.000 claims description 15
- 125000004450 alkenylene group Chemical group 0.000 claims description 15
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 13
- 125000004423 acyloxy group Chemical group 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical group C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 claims description 11
- 125000001544 thienyl group Chemical group 0.000 claims description 11
- QYCGBAJADAGLLK-UHFFFAOYSA-N 1-(cyclohepten-1-yl)cycloheptene Chemical group C1CCCCC=C1C1=CCCCCC1 QYCGBAJADAGLLK-UHFFFAOYSA-N 0.000 claims description 10
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- 125000001041 indolyl group Chemical group 0.000 claims description 9
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 206010020772 Hypertension Diseases 0.000 claims description 8
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 8
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 7
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 7
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 claims description 7
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 5
- KVFIFVMFYLZJBZ-LSCFUAHRSA-N (2r,3r,4s,5r)-2-[6-amino-2-(2-cyclohexylethylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound N=1C=2N([C@H]3[C@@H]([C@H](O)[C@@H](CO)O3)O)C=NC=2C(N)=NC=1NCCC1CCCCC1 KVFIFVMFYLZJBZ-LSCFUAHRSA-N 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 3
- PZXWQOIRBVHQTI-AEVYOOLXSA-N 3-[4-[2-[[6-amino-9-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-2-yl]amino]ethyl]phenyl]propanoic acid Chemical compound N=1C=2N([C@H]3[C@@H]([C@H](O)[C@@H](CO)O3)O)C=NC=2C(N)=NC=1NCCC1=CC=C(CCC(O)=O)C=C1 PZXWQOIRBVHQTI-AEVYOOLXSA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 230000003276 anti-hypertensive effect Effects 0.000 claims 2
- SLUGAKUMOFIJEH-LSCFUAHRSA-N (2r,3r,4s,5r)-2-[6-amino-2-[2-(cyclohexen-1-yl)ethylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound N=1C=2N([C@H]3[C@@H]([C@H](O)[C@@H](CO)O3)O)C=NC=2C(N)=NC=1NCCC1=CCCCC1 SLUGAKUMOFIJEH-LSCFUAHRSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 78
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 75
- 239000000203 mixture Substances 0.000 description 71
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 62
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
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- 239000002904 solvent Substances 0.000 description 25
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- BIXYYZIIJIXVFW-UUOKFMHZSA-N (2R,3R,4S,5R)-2-(6-amino-2-chloro-9-purinyl)-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C1=NC=2C(N)=NC(Cl)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O BIXYYZIIJIXVFW-UUOKFMHZSA-N 0.000 description 18
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- 239000007858 starting material Substances 0.000 description 17
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- 150000001412 amines Chemical class 0.000 description 15
- 239000000741 silica gel Substances 0.000 description 15
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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 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
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- 230000000875 corresponding effect Effects 0.000 description 6
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- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- CMJIKWRJLCDJQU-UHFFFAOYSA-N tert-butyl 2-[4-(2-aminoethyl)phenyl]acetate Chemical compound CC(C)(C)OC(=O)CC1=CC=C(CCN)C=C1 CMJIKWRJLCDJQU-UHFFFAOYSA-N 0.000 description 1
- BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 1
- NGPXHZLYCMQAOP-UHFFFAOYSA-N tert-butyl 3-[4-(2-aminoethyl)cyclohexyl]propanoate Chemical compound CC(C)(C)OC(=O)CCC1CCC(CCN)CC1 NGPXHZLYCMQAOP-UHFFFAOYSA-N 0.000 description 1
- AREBZMHRZKQVFT-UHFFFAOYSA-N tert-butyl 3-[4-(2-aminoethyl)phenyl]propanoate Chemical compound CC(C)(C)OC(=O)CCC1=CC=C(CCN)C=C1 AREBZMHRZKQVFT-UHFFFAOYSA-N 0.000 description 1
- UMCMYPLVMHGXJX-UHFFFAOYSA-N tert-butyl 3-[4-(cyanomethyl)phenyl]propanoate Chemical compound CC(C)(C)OC(=O)CCC1=CC=C(CC#N)C=C1 UMCMYPLVMHGXJX-UHFFFAOYSA-N 0.000 description 1
- QDJGUTKVTOLTLO-HAXDFEGKSA-N tert-butyl 3-[5-[2-[[6-amino-9-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-2-yl]amino]ethyl]thiophen-3-yl]propanoate Chemical compound CC(C)(C)OC(=O)CCC1=CSC(CCNC=2N=C3N([C@H]4[C@@H]([C@H](O)[C@@H](CO)O4)O)C=NC3=C(N)N=2)=C1 QDJGUTKVTOLTLO-HAXDFEGKSA-N 0.000 description 1
- YWDPABSCINWVNP-WVSUBDOOSA-N tert-butyl 4-[2-[[6-amino-9-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-2-yl]amino]ethyl]benzoate Chemical compound C1=CC(C(=O)OC(C)(C)C)=CC=C1CCNC1=NC(N)=C(N=CN2[C@H]3[C@@H]([C@H](O)[C@@H](CO)O3)O)C2=N1 YWDPABSCINWVNP-WVSUBDOOSA-N 0.000 description 1
- ZMZFEEBOYDRFCQ-UHFFFAOYSA-N tert-butyl n-(5-methoxy-3,4-dihydro-2h-thiochromen-3-yl)carbamate Chemical compound S1CC(NC(=O)OC(C)(C)C)CC2=C1C=CC=C2OC ZMZFEEBOYDRFCQ-UHFFFAOYSA-N 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YNVOMSDITJMNET-UHFFFAOYSA-N thiophene-3-carboxylic acid Chemical compound OC(=O)C=1C=CSC=1 YNVOMSDITJMNET-UHFFFAOYSA-N 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical class OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical class [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
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
- C07H19/173—Purine radicals with 2-deoxyribosyl 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
- 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
- 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
-
- 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
- A61P9/12—Antihypertensives
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)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biotechnology (AREA)
- Pharmacology & Pharmacy (AREA)
- Genetics & Genomics (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14205588A | 1988-01-07 | 1988-01-07 | |
| US07/193,968 US5034381A (en) | 1988-01-07 | 1988-05-13 | 2-(substituted amino) adenosines as antihypertensives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PH26672A true PH26672A (en) | 1992-09-15 |
Family
ID=26839719
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PH39015A PH26672A (en) | 1988-01-07 | 1989-01-06 | 2-(substituted amino) adenosines as antihypertensives |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US5034381A (fi) |
| EP (1) | EP0323807A3 (fi) |
| JP (1) | JPH01265100A (fi) |
| KR (1) | KR890011903A (fi) |
| AU (1) | AU618055B2 (fi) |
| CA (1) | CA1325209C (fi) |
| DD (1) | DD283402A5 (fi) |
| DK (1) | DK5089A (fi) |
| FI (1) | FI90430C (fi) |
| HU (1) | HU202550B (fi) |
| IL (1) | IL88877A0 (fi) |
| MX (1) | MX14446A (fi) |
| NO (1) | NO169843C (fi) |
| NZ (1) | NZ227542A (fi) |
| PH (1) | PH26672A (fi) |
| PT (1) | PT89392B (fi) |
| ZA (1) | ZA8984B (fi) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4977144A (en) * | 1988-08-02 | 1990-12-11 | Ciba-Geigy Corporation | Imidazo[4,5-b]pyridine derivatives as cardiovascular agents |
| AU3820989A (en) * | 1988-08-02 | 1990-02-08 | Ciba-Geigy Ag | 7-amino-3-beta-d-ribofuranosyl-3h-imidazo(4,5-b) pyridin-5-amine derivatives |
| US5189027A (en) | 1990-11-30 | 1993-02-23 | Yamasa Shoyu Kabushiki Kaisha | 2-substituted adenosine derivatives and pharmaceutical compositions for circulatory diseases |
| US5206222A (en) * | 1991-05-22 | 1993-04-27 | Vanderbilt University | Methods for the reduction of myocardial reperfusion injury |
| IT1254915B (it) * | 1992-04-24 | 1995-10-11 | Gloria Cristalli | Derivati di adenosina ad attivita' a2 agonista |
| IL107101A0 (en) * | 1992-09-30 | 1993-12-28 | Merrell Dow Pharma | 2-substituted adenosines with a-2 receptor affinity |
| US5426101A (en) * | 1992-09-30 | 1995-06-20 | Merrell Dow Pharmaceuticals Inc. | 2-substituted adenosines with A-2 receptor affinity |
| WO1994023723A1 (en) * | 1993-04-15 | 1994-10-27 | New York University | Adenosine receptor agonists for the promotion of wound healing |
| US5817641A (en) * | 1994-07-21 | 1998-10-06 | Thomas Jefferson University | Treatment of enterotoxigenic diarrhea with 2-substituted adenosine derivatives |
| AU740770B2 (en) | 1997-06-18 | 2001-11-15 | Aderis Pharmaceuticals, 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 |
| WO1999017784A1 (en) | 1997-10-07 | 1999-04-15 | Regents Of The University Of California Corporation | Treating occlusive peripheral vascular disease and coronary disease with combinations of heparin and an adenoside a2 agonist, or with adenosine |
| AU751470B2 (en) * | 1998-07-09 | 2002-08-15 | Sequella, Inc. | Novel antibacterial compounds |
| AU4343500A (en) | 1999-04-16 | 2000-11-02 | Schering Corporation | Use of azetidinone compounds |
| TWI245047B (en) * | 1999-08-20 | 2005-12-11 | Sankyo Co | Novel A-500359 derivatives |
| US20050033044A1 (en) | 2003-05-19 | 2005-02-10 | Bristol-Myers Squibb Pharma Company | Methods for preparing 2-alkynyladenosine derivatives |
| MX2007009783A (es) | 2005-02-17 | 2007-08-22 | Wyeth Corp | Derivados de indol, benzotiofeno, benzofurano e indeno cicloalquilfusionados. |
| US20090136460A1 (en) * | 2007-07-10 | 2009-05-28 | Vanderbilt University | Use of adenosine receptor ligands to promote cell adhesion in cell-based therapies |
| AU2014340114B2 (en) * | 2013-10-23 | 2018-10-18 | Academia Sinica | Compounds for use in prevention and treatment of neurodegenerative diseases and pain |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1670265A1 (de) * | 1967-08-25 | 1971-01-28 | Boehringer Mannheim Gmbh | 2-Amino-Adenosinderivate und Verfahren zu deren Herstellung |
| NL7203984A (fi) * | 1971-04-10 | 1972-10-12 | ||
| US3917583A (en) * | 1972-08-04 | 1975-11-04 | Icn Pharmaceuticals | 2-Substituted cyclic AMP derivatives |
| AR205247A1 (es) * | 1973-02-07 | 1976-04-21 | Icn Pharmaceuticals | Procedimiento para preparar derivados de amp 2-substituidos |
| JPS5630355B2 (fi) * | 1974-01-21 | 1981-07-14 | ||
| AU5118979A (en) * | 1978-10-16 | 1980-04-24 | Takeda Chemical Industries Ltd. | 2,6-diaminoebularines |
| JPS55139399A (en) * | 1979-04-12 | 1980-10-31 | Asahi Chem Ind Co Ltd | Novel adenosine derivative substituted in the 2-position |
| JPS56152437U (fi) * | 1980-04-14 | 1981-11-14 | ||
| US4501735A (en) * | 1983-12-05 | 1985-02-26 | Warner-Lambert Company | N6-(1- and 2-benzocycloalkyl) adenosines |
| DE3406533A1 (de) * | 1984-02-23 | 1985-08-29 | Boehringer Mannheim Gmbh, 6800 Mannheim | Verwendung von adenosin-derivaten als antiallergica und arzneimittel, die diese enthalten |
| DE3587717T2 (de) * | 1984-04-18 | 1994-04-28 | Whitby Research Inc | N-6-thienyl-substituierte Adenosinderivate als herzgefässerweiternde Mittel. |
| US4594350A (en) * | 1984-07-30 | 1986-06-10 | Reagents Of University Of Minnesota | (3-ethoxypropionate) esters of cyclaradine |
| US4683223A (en) * | 1985-09-09 | 1987-07-28 | Warner-Lambert Company | N6 -Benzopyrano-and benzothiopyrano adenosines and methods of use |
| US4593019A (en) * | 1984-10-26 | 1986-06-03 | Warner-Lambert Company | N6 -tricyclic adenosines |
| US4791103A (en) * | 1985-02-08 | 1988-12-13 | Warner-Lambert Company | 2,N6 -disubstituted adenosines, derivatives and methods of use |
| US4600707A (en) * | 1985-01-25 | 1986-07-15 | Warner-Lambert Company | Benzothien-3-yl adenosine; benzothien-3-yl adenosine, S-oxide; and benzothien-3-yl, S,S-dioxide adenosine compounds |
| US4755594A (en) * | 1986-01-31 | 1988-07-05 | Warner-Lambert Company | N6 -substituted adenosines |
| US4843066A (en) * | 1986-11-27 | 1989-06-27 | Nippon Zoki Pharmaceutical Co., Ltd. | Novel adenosine derivatives and pharmaceutical composition containing them as an active ingredient |
| EP0277917A3 (en) * | 1987-02-04 | 1990-03-28 | Ciba-Geigy Ag | Certain adenosine 5'-carboxamide derivatives |
-
1988
- 1988-05-13 US US07/193,968 patent/US5034381A/en not_active Expired - Fee Related
- 1988-12-29 EP EP88810900A patent/EP0323807A3/en not_active Withdrawn
- 1988-12-30 NO NO885821A patent/NO169843C/no unknown
-
1989
- 1989-01-03 IL IL88877A patent/IL88877A0/xx unknown
- 1989-01-04 FI FI890028A patent/FI90430C/fi not_active IP Right Cessation
- 1989-01-05 PT PT89392A patent/PT89392B/pt not_active IP Right Cessation
- 1989-01-05 CA CA000587534A patent/CA1325209C/en not_active Expired - Fee Related
- 1989-01-05 MX MX1444689A patent/MX14446A/es unknown
- 1989-01-05 ZA ZA8984A patent/ZA8984B/xx unknown
- 1989-01-05 HU HU8933A patent/HU202550B/hu not_active IP Right Cessation
- 1989-01-05 DD DD89324859A patent/DD283402A5/de unknown
- 1989-01-05 NZ NZ227542A patent/NZ227542A/en unknown
- 1989-01-06 PH PH39015A patent/PH26672A/en unknown
- 1989-01-06 DK DK005089A patent/DK5089A/da not_active Application Discontinuation
- 1989-01-06 JP JP64000590A patent/JPH01265100A/ja active Pending
- 1989-01-06 AU AU27767/89A patent/AU618055B2/en not_active Ceased
- 1989-01-06 KR KR1019890000062A patent/KR890011903A/ko not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CA1325209C (en) | 1993-12-14 |
| FI90430B (fi) | 1993-10-29 |
| NO169843C (no) | 1992-08-12 |
| DD283402A5 (de) | 1990-10-10 |
| US5034381A (en) | 1991-07-23 |
| NO885821D0 (no) | 1988-12-30 |
| JPH01265100A (ja) | 1989-10-23 |
| MX14446A (es) | 1994-01-31 |
| HU202550B (en) | 1991-03-28 |
| AU2776789A (en) | 1989-07-13 |
| FI890028A0 (fi) | 1989-01-04 |
| EP0323807A3 (en) | 1990-06-20 |
| PT89392B (pt) | 1993-09-30 |
| NZ227542A (en) | 1992-03-26 |
| IL88877A0 (en) | 1989-08-15 |
| FI890028A (fi) | 1989-07-08 |
| ZA8984B (en) | 1989-08-30 |
| PT89392A (pt) | 1990-02-08 |
| DK5089D0 (da) | 1989-01-06 |
| NO885821L (no) | 1989-07-10 |
| AU618055B2 (en) | 1991-12-12 |
| HUT48904A (en) | 1989-07-28 |
| FI90430C (fi) | 1994-02-10 |
| EP0323807A2 (en) | 1989-07-12 |
| NO169843B (no) | 1992-05-04 |
| DK5089A (da) | 1989-07-08 |
| KR890011903A (ko) | 1989-08-23 |
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