CA1320205C - 1,4-dihydro-4-(nitro)phenyl-3,5-pyridinecarboxylates incorporating an alkylaminoalkylene-heteroatom group moiety on one of the carboxylate groups - Google Patents
1,4-dihydro-4-(nitro)phenyl-3,5-pyridinecarboxylates incorporating an alkylaminoalkylene-heteroatom group moiety on one of the carboxylate groupsInfo
- Publication number
- CA1320205C CA1320205C CA000534742A CA534742A CA1320205C CA 1320205 C CA1320205 C CA 1320205C CA 000534742 A CA000534742 A CA 000534742A CA 534742 A CA534742 A CA 534742A CA 1320205 C CA1320205 C CA 1320205C
- Authority
- CA
- Canada
- Prior art keywords
- compound
- methyl
- dihydro
- phenyl
- propyl
- 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
Links
- 150000007942 carboxylates Chemical group 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 116
- 239000002253 acid Substances 0.000 claims abstract description 11
- 208000028867 ischemia Diseases 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- 239000000126 substance Substances 0.000 claims abstract description 10
- 210000001772 blood platelet Anatomy 0.000 claims abstract description 8
- 230000005764 inhibitory process Effects 0.000 claims abstract description 7
- -1 3-indolyl ring Chemical group 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 206010020772 Hypertension Diseases 0.000 claims description 6
- 231100000252 nontoxic Toxicity 0.000 claims description 6
- 230000003000 nontoxic effect Effects 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 101100516568 Caenorhabditis elegans nhr-7 gene Chemical group 0.000 claims description 3
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 3
- 241000124008 Mammalia Species 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 230000003276 anti-hypertensive effect Effects 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical group 0.000 claims description 3
- 150000003462 sulfoxides Chemical class 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 230000001225 therapeutic effect Effects 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 4
- TZDPJNSHSWMCPN-UHFFFAOYSA-N 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid Chemical compound OC(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC([N+]([O-])=O)=C1 TZDPJNSHSWMCPN-UHFFFAOYSA-N 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- OJDYTYYKJJWCFL-UHFFFAOYSA-N 3-O-methyl 5-O-[3-(2-phenylsulfanylethylamino)propyl] 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CC=1NC(=C(C(C=1C(=O)OC)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCCCNCCSC1=CC=CC=C1)C OJDYTYYKJJWCFL-UHFFFAOYSA-N 0.000 claims 1
- FFKAGWNAOXDGFH-UHFFFAOYSA-N 3-O-methyl 5-O-[3-[methyl(2-phenylsulfanylethyl)amino]propyl] 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CC=1NC(=C(C(C=1C(=O)OC)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCCCN(CCSC1=CC=CC=C1)C)C FFKAGWNAOXDGFH-UHFFFAOYSA-N 0.000 claims 1
- BCKYEOKGALUXOL-UHFFFAOYSA-N 5-O-[3-(2-anilinoethylamino)propyl] 3-O-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CC=1NC(=C(C(C=1C(=O)OC)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCCCNCCNC1=CC=CC=C1)C BCKYEOKGALUXOL-UHFFFAOYSA-N 0.000 claims 1
- WLJGSMKDTGZXCT-UHFFFAOYSA-N 5-O-[3-[2-(2-methoxyphenyl)sulfanylethyl-methylamino]propyl] 3-O-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CC=1NC(=C(C(C1C(=O)OCCCN(C)CCSC1=C(C=CC=C1)OC)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OC)C WLJGSMKDTGZXCT-UHFFFAOYSA-N 0.000 claims 1
- HIEXESOVELNDRA-UHFFFAOYSA-N 5-O-[3-[2-(4-tert-butyl-2-methylphenyl)sulfanylethyl-methylamino]propyl] 3-O-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CC=1NC(=C(C(C=1C(=O)OC)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCCCN(CCSC1=C(C=C(C=C1)C(C)(C)C)C)C)C HIEXESOVELNDRA-UHFFFAOYSA-N 0.000 claims 1
- YNGQLSCAOXRLCT-UHFFFAOYSA-N 5-O-[3-[2-(benzenesulfinyl)ethyl-methylamino]propyl] 3-O-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CC=1NC(=C(C(C=1C(=O)OC)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCCCN(CCS(=O)C1=CC=CC=C1)C)C YNGQLSCAOXRLCT-UHFFFAOYSA-N 0.000 claims 1
- DJAUQCLTKOZKIP-UHFFFAOYSA-N 5-O-[3-[2-anilinoethyl(methyl)amino]propyl] 3-O-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CC=1NC(=C(C(C=1C(=O)OC)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCCCN(C)CCNC1=CC=CC=C1)C DJAUQCLTKOZKIP-UHFFFAOYSA-N 0.000 claims 1
- GUXPCYIUJVCLIB-UHFFFAOYSA-N 5-O-[3-[benzyl(2-phenylsulfanylethyl)amino]propyl] 3-O-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CC=1NC(=C(C(C=1C(=O)OC)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCCCN(CCSC1=CC=CC=C1)CC1=CC=CC=C1)C GUXPCYIUJVCLIB-UHFFFAOYSA-N 0.000 claims 1
- JPXPPUOCSLMCHK-UHFFFAOYSA-N 5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid Chemical compound COC(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC([N+]([O-])=O)=C1 JPXPPUOCSLMCHK-UHFFFAOYSA-N 0.000 claims 1
- PAWKEAATSXRATL-UHFFFAOYSA-N 5-o-[3-[benzyl-[2-(n-methylanilino)ethyl]amino]propyl] 3-o-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCCN(CCN(C)C=2C=CC=CC=2)CC=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 PAWKEAATSXRATL-UHFFFAOYSA-N 0.000 claims 1
- RMVOOUOQZQNHLK-UHFFFAOYSA-N Cl.CC=1NC(=C(C(C1C(=O)OC)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCCCN(CCSC1=CC=CC=C1)CCSC1=CC=CC=C1)C Chemical compound Cl.CC=1NC(=C(C(C1C(=O)OC)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCCCN(CCSC1=CC=CC=C1)CCSC1=CC=CC=C1)C RMVOOUOQZQNHLK-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 18
- 230000000694 effects Effects 0.000 abstract description 10
- 230000000144 pharmacologic effect Effects 0.000 abstract description 5
- 230000003287 optical effect Effects 0.000 abstract description 4
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 abstract description 3
- 229910001424 calcium ion Inorganic materials 0.000 abstract description 3
- 208000010110 spontaneous platelet aggregation Diseases 0.000 abstract description 3
- 208000037816 tissue injury Diseases 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 239000000543 intermediate Substances 0.000 description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- 239000000243 solution Substances 0.000 description 26
- 239000003921 oil Substances 0.000 description 24
- 238000000034 method Methods 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 13
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 10
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 125000002947 alkylene group Chemical group 0.000 description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
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- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 7
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61P9/08—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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
- C07D211/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (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)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/852,856 US4814455A (en) | 1986-04-16 | 1986-04-16 | Dihydro-3,5-dicarboxylates |
| US852,856 | 1992-03-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1320205C true CA1320205C (en) | 1993-07-13 |
Family
ID=25314403
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000534742A Expired - Fee Related CA1320205C (en) | 1986-04-16 | 1987-04-15 | 1,4-dihydro-4-(nitro)phenyl-3,5-pyridinecarboxylates incorporating an alkylaminoalkylene-heteroatom group moiety on one of the carboxylate groups |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4814455A (OSRAM) |
| EP (1) | EP0247345A3 (OSRAM) |
| JP (1) | JPS62281860A (OSRAM) |
| CA (1) | CA1320205C (OSRAM) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0696552B2 (ja) * | 1985-08-21 | 1994-11-30 | グラクソ・ソシエタ・ペル・アツイオ−ニ | 複素環式化合物 |
| US5602174A (en) * | 1986-02-15 | 1997-02-11 | Beecham Wuefling Gmbh & Co. | Treatment |
| GB8603765D0 (en) * | 1986-02-15 | 1986-03-19 | Beecham Wuelfung Gmbh & Co Kg | Compounds |
| JPS63112560A (ja) * | 1986-10-29 | 1988-05-17 | Green Cross Corp:The | ジヒドロピリジン誘導体 |
| DE4131346A1 (de) * | 1991-09-20 | 1993-03-25 | Bayer Ag | Indolsulfonamid substituierte dihydropyridine, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln |
| DE4222770A1 (de) * | 1992-07-10 | 1994-01-13 | Bayer Ag | Lichtaktivierbare 1-(2-Nitrobenzyl)-substituierte 1,4-Dihydropyridine |
| JP4734924B2 (ja) * | 2004-01-13 | 2011-07-27 | 三菱瓦斯化学株式会社 | 環状カルバミン酸エステルの製造方法 |
| JP6555702B2 (ja) * | 2016-01-26 | 2019-08-07 | アタトゥルク ユニヴァーシテシ ビリムセル アラスティルマ プロジェレリ ビリミ | Ｎ３，ｎ５‐ビス（２‐（５‐メトキシ‐１ｈ‐インドール‐３‐イル）エチル）‐２，６‐ジメチル‐４‐（２‐ニトロフェニル）ピリジン‐３，５‐ジカルボキシアミドおよび神経毒分野におけるその使用 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1670827C3 (de) * | 1967-03-20 | 1974-10-24 | Bayer Ag, 5090 Leverkusen | 4-(2'-Nitrophenyl)-2,6-dimethyl-3,5-dicarbmethoxy-1,4-dihydropyridin |
| US3883543A (en) * | 1969-05-10 | 1975-05-13 | Bayer Ag | N-alkyl-1,4-dihydropyridines |
| CH603575A5 (OSRAM) * | 1974-08-19 | 1978-08-31 | Hoffmann La Roche | |
| JPS5762257A (en) * | 1980-10-03 | 1982-04-15 | Yoshitomi Pharmaceut Ind Ltd | 1,4-dihydropyridine-3,5-dicarboxylic acid ester or its salt |
| DE3207982A1 (de) * | 1982-03-05 | 1983-09-08 | Bayer Ag, 5090 Leverkusen | Neue 1,4-dihydropyridine, verfahren zu ihrer herstellung und ihrer verwendung in arzneimitteln |
| DE3208628A1 (de) * | 1982-03-10 | 1983-09-22 | Bayer Ag, 5090 Leverkusen | Neue verbindungen, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| WO1983003249A1 (en) * | 1982-03-17 | 1983-09-29 | Yoshitomi Pharmaceutical | 1,4-dihydropyridine-3,5-dicarboxylate derivatives |
| ATE50987T1 (de) * | 1982-05-10 | 1990-03-15 | Takeda Chemical Industries Ltd | Dihydropyridinderivate, deren herstellung und verwendung. |
| IL68524A0 (en) * | 1982-05-21 | 1983-07-31 | Haessle Ab | Novel dihydropyridines |
| EP0097821B1 (en) * | 1982-06-03 | 1988-07-13 | Pierrel S.p.A. | Dihydropyridines with an antagonistic activity to calcium, process for their preparation, and pharmaceutical compositions containing them |
| AU561213B2 (en) * | 1983-06-02 | 1987-04-30 | Teijin Limited | 1, 4-dihydropyridine derivative |
| JPS60120861A (ja) * | 1983-12-02 | 1985-06-28 | Otsuka Pharmaceut Co Ltd | ジヒドロピリジン誘導体 |
| JPS60156671A (ja) * | 1984-01-25 | 1985-08-16 | Yamanouchi Pharmaceut Co Ltd | ジヒドロピリジン誘導体およびその製造法 |
| IL77843A (en) * | 1985-02-11 | 1989-07-31 | Syntex Inc | Dihydropyridine derivatives,process and novel intermediates for their preparation and pharmaceutical compositions containing them |
-
1986
- 1986-04-16 US US06/852,856 patent/US4814455A/en not_active Expired - Fee Related
-
1987
- 1987-04-15 EP EP87105601A patent/EP0247345A3/en not_active Ceased
- 1987-04-15 CA CA000534742A patent/CA1320205C/en not_active Expired - Fee Related
- 1987-04-16 JP JP62092129A patent/JPS62281860A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62281860A (ja) | 1987-12-07 |
| EP0247345A2 (en) | 1987-12-02 |
| EP0247345A3 (en) | 1987-12-23 |
| JPH0515704B2 (OSRAM) | 1993-03-02 |
| US4814455A (en) | 1989-03-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |