DE2847236A1 - Neue dihydropyridine mit substituierten estergruppierungen, mehrer verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel - Google Patents
Neue dihydropyridine mit substituierten estergruppierungen, mehrer verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittelInfo
- Publication number
- DE2847236A1 DE2847236A1 DE19782847236 DE2847236A DE2847236A1 DE 2847236 A1 DE2847236 A1 DE 2847236A1 DE 19782847236 DE19782847236 DE 19782847236 DE 2847236 A DE2847236 A DE 2847236A DE 2847236 A1 DE2847236 A1 DE 2847236A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- alkyl
- ester
- formula
- optionally
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims abstract description 50
- 150000002148 esters Chemical group 0.000 title claims description 102
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 title abstract description 7
- 229940126601 medicinal product Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 32
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- -1 Pyrryl Chemical group 0.000 claims description 142
- 125000004432 carbon atom Chemical group C* 0.000 claims description 62
- 125000000217 alkyl group Chemical group 0.000 claims description 53
- 239000002253 acid Substances 0.000 claims description 33
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 20
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 19
- 239000003960 organic solvent Substances 0.000 claims description 17
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
- 125000004663 dialkyl amino group Chemical group 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 14
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 125000004434 sulfur atom Chemical group 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- 229920006395 saturated elastomer Polymers 0.000 claims description 11
- 125000003277 amino group Chemical group 0.000 claims description 10
- 125000004122 cyclic group Chemical group 0.000 claims description 10
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 9
- 150000005840 aryl radicals Chemical class 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 8
- 150000001299 aldehydes Chemical class 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 125000004185 ester group Chemical group 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000000468 ketone group Chemical group 0.000 claims description 8
- 150000003254 radicals Chemical class 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 7
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 150000002170 ethers Chemical class 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000002560 nitrile group Chemical group 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000005493 quinolyl group Chemical group 0.000 claims description 3
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000012876 carrier material Substances 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 91
- UKVYVZLTGQVOPX-IHWYPQMZSA-N (z)-3-aminobut-2-enoic acid Chemical compound C\C(N)=C\C(O)=O UKVYVZLTGQVOPX-IHWYPQMZSA-N 0.000 description 40
- 235000019441 ethanol Nutrition 0.000 description 40
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 29
- 239000002904 solvent Substances 0.000 description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 26
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 15
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- 229960000583 acetic acid Drugs 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 12
- 239000000126 substance Substances 0.000 description 11
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 150000001298 alcohols Chemical class 0.000 description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
- 229910052794 bromium Inorganic materials 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 238000009835 boiling Methods 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 239000003085 diluting agent Substances 0.000 description 7
- 229910052731 fluorine Inorganic materials 0.000 description 7
- 239000011737 fluorine Substances 0.000 description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- 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 description 4
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 3
- 239000001431 2-methylbenzaldehyde Substances 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 229930195734 saturated hydrocarbon Chemical group 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 235000012222 talc Nutrition 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 230000002792 vascular Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- WSGYTJNNHPZFKR-UHFFFAOYSA-N 3-hydroxypropanenitrile Chemical compound OCCC#N WSGYTJNNHPZFKR-UHFFFAOYSA-N 0.000 description 2
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 2
- ISDBWOPVZKNQDW-UHFFFAOYSA-N 4-phenylbenzaldehyde Chemical compound C1=CC(C=O)=CC=C1C1=CC=CC=C1 ISDBWOPVZKNQDW-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 238000006000 Knoevenagel condensation reaction Methods 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 229940022663 acetate Drugs 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 125000000068 chlorophenyl group Chemical group 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 210000004351 coronary vessel Anatomy 0.000 description 2
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- ZSKGQVFRTSEPJT-UHFFFAOYSA-N pyrrole-2-carboxaldehyde Chemical compound O=CC1=CC=CN1 ZSKGQVFRTSEPJT-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000011435 rock Substances 0.000 description 2
- 210000002460 smooth muscle Anatomy 0.000 description 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 230000001256 tonic effect Effects 0.000 description 2
- HLWBJJVWUSLSEZ-UHFFFAOYSA-N (3-cyano-3-phenylpropyl) acetate Chemical compound CC(=O)OCCC(C#N)c1ccccc1 HLWBJJVWUSLSEZ-UHFFFAOYSA-N 0.000 description 1
- XCJLNYCUYTWYQU-UHFFFAOYSA-N (3-cyanocyclopentyl) 3-oxobutanoate Chemical compound CC(=O)CC(=O)OC1CCC(C#N)C1 XCJLNYCUYTWYQU-UHFFFAOYSA-N 0.000 description 1
- SIYHTTIDRINZMO-UHFFFAOYSA-N (4-cyanocyclohexyl) 3-oxobutanoate Chemical compound CC(=O)CC(=O)OC1CCC(C#N)CC1 SIYHTTIDRINZMO-UHFFFAOYSA-N 0.000 description 1
- OSLAYKKXCYSJSF-ARJAWSKDSA-N (Z)-4-aminopent-3-en-2-one Chemical compound C\C(N)=C\C(C)=O OSLAYKKXCYSJSF-ARJAWSKDSA-N 0.000 description 1
- WNVZOHNNPDZYFN-UHFFFAOYSA-N 1,2-oxazole-3-carbaldehyde Chemical compound O=CC=1C=CON=1 WNVZOHNNPDZYFN-UHFFFAOYSA-N 0.000 description 1
- TYHOSUCCUICRLM-UHFFFAOYSA-N 1,3-oxazole-2-carbaldehyde Chemical compound O=CC1=NC=CO1 TYHOSUCCUICRLM-UHFFFAOYSA-N 0.000 description 1
- ZGTFNNUASMWGTM-UHFFFAOYSA-N 1,3-thiazole-2-carbaldehyde Chemical compound O=CC1=NC=CS1 ZGTFNNUASMWGTM-UHFFFAOYSA-N 0.000 description 1
- WVKJXBFKFFMORO-UHFFFAOYSA-N 1-(2-methylpropylsulfonyl)propan-2-one Chemical compound CC(C)CS(=O)(=O)CC(C)=O WVKJXBFKFFMORO-UHFFFAOYSA-N 0.000 description 1
- SKYVAGABDXUVRW-UHFFFAOYSA-N 1-(4-methoxyphenyl)sulfonylpropan-2-one Chemical compound COC1=CC=C(S(=O)(=O)CC(C)=O)C=C1 SKYVAGABDXUVRW-UHFFFAOYSA-N 0.000 description 1
- VEHMTJMOIAQEIF-UHFFFAOYSA-N 1-(4-tert-butylphenyl)sulfonylpropan-2-one Chemical compound CC(=O)CS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 VEHMTJMOIAQEIF-UHFFFAOYSA-N 0.000 description 1
- YBLGSNMIIPIRFC-UHFFFAOYSA-N 1-(benzenesulfonyl)propan-2-one Chemical compound CC(=O)CS(=O)(=O)C1=CC=CC=C1 YBLGSNMIIPIRFC-UHFFFAOYSA-N 0.000 description 1
- JZGXSTFDSZFGMC-UHFFFAOYSA-N 1-benzylsulfonylpropan-2-one Chemical compound CC(=O)CS(=O)(=O)CC1=CC=CC=C1 JZGXSTFDSZFGMC-UHFFFAOYSA-N 0.000 description 1
- QZVULAHMNBLATB-UHFFFAOYSA-N 1-butylsulfonylpropan-2-one Chemical compound CCCCS(=O)(=O)CC(C)=O QZVULAHMNBLATB-UHFFFAOYSA-N 0.000 description 1
- PNXDIRMMLHZCBU-UHFFFAOYSA-N 1-cyanopropan-2-yl 3-oxobutanoate Chemical compound N#CCC(C)OC(=O)CC(C)=O PNXDIRMMLHZCBU-UHFFFAOYSA-N 0.000 description 1
- SUOHLNLXYCLNKA-UHFFFAOYSA-N 1-ethylsulfonyl-n-methylprop-1-en-2-amine Chemical compound CCS(=O)(=O)C=C(C)NC SUOHLNLXYCLNKA-UHFFFAOYSA-N 0.000 description 1
- NWEYGXQKFVGUFR-UHFFFAOYSA-N 1-methylsulfonylpropan-2-one Chemical compound CC(=O)CS(C)(=O)=O NWEYGXQKFVGUFR-UHFFFAOYSA-N 0.000 description 1
- ZOWSJJBOQDKOHI-UHFFFAOYSA-N 2,2,2-trifluoroethyl acetate Chemical compound CC(=O)OCC(F)(F)F ZOWSJJBOQDKOHI-UHFFFAOYSA-N 0.000 description 1
- GISVICWQYMUPJF-UHFFFAOYSA-N 2,4-Dimethylbenzaldehyde Chemical compound CC1=CC=C(C=O)C(C)=C1 GISVICWQYMUPJF-UHFFFAOYSA-N 0.000 description 1
- DMIYKWPEFRFTPY-UHFFFAOYSA-N 2,6-dichlorobenzaldehyde Chemical compound ClC1=CC=CC(Cl)=C1C=O DMIYKWPEFRFTPY-UHFFFAOYSA-N 0.000 description 1
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- YPMPTULBFPFSEQ-PLNGDYQASA-N ethyl (z)-3-aminobut-2-enoate Chemical compound CCOC(=O)\C=C(\C)N YPMPTULBFPFSEQ-PLNGDYQASA-N 0.000 description 1
- XZYGRRSTJVFZLS-UHFFFAOYSA-N ethyl 3-formylbenzoate Chemical compound CCOC(=O)C1=CC=CC(C=O)=C1 XZYGRRSTJVFZLS-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000019264 food flavour enhancer Nutrition 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- OLNJUISKUQQNIM-UHFFFAOYSA-N indole-3-carbaldehyde Chemical compound C1=CC=C2C(C=O)=CNC2=C1 OLNJUISKUQQNIM-UHFFFAOYSA-N 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- HORFVOWTVOJVAN-UHFFFAOYSA-N isoquinoline-1-carbaldehyde Chemical compound C1=CC=C2C(C=O)=NC=CC2=C1 HORFVOWTVOJVAN-UHFFFAOYSA-N 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- OVWYEQOVUDKZNU-UHFFFAOYSA-N m-tolualdehyde Chemical compound CC1=CC=CC(C=O)=C1 OVWYEQOVUDKZNU-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- XKORCTIIRYKLLG-ARJAWSKDSA-N methyl (z)-3-aminobut-2-enoate Chemical compound COC(=O)\C=C(\C)N XKORCTIIRYKLLG-ARJAWSKDSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- BTFQKIATRPGRBS-UHFFFAOYSA-N o-tolualdehyde Chemical compound CC1=CC=CC=C1C=O BTFQKIATRPGRBS-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- MDHYEMXUFSJLGV-UHFFFAOYSA-N phenethyl acetate Chemical compound CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- BVMNCGXSFZQPNI-HWKANZROSA-N prop-2-ynyl (E)-but-2-enoate Chemical compound C\C=C\C(=O)OCC#C BVMNCGXSFZQPNI-HWKANZROSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- DXBWJLDFSICTIH-UHFFFAOYSA-N pyrazine-2-carbaldehyde Chemical compound O=CC1=CN=CC=N1 DXBWJLDFSICTIH-UHFFFAOYSA-N 0.000 description 1
- BZORCBQGFKOHMY-UHFFFAOYSA-N pyridazine-4-carbaldehyde Chemical compound O=CC1=CC=NN=C1 BZORCBQGFKOHMY-UHFFFAOYSA-N 0.000 description 1
- QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- YIYRXCXJFKZQBC-UHFFFAOYSA-N quinazoline-2-carbaldehyde Chemical compound C1=CC=CC2=NC(C=O)=NC=C21 YIYRXCXJFKZQBC-UHFFFAOYSA-N 0.000 description 1
- MGCGJBXTNWUHQE-UHFFFAOYSA-N quinoline-4-carbaldehyde Chemical compound C1=CC=C2C(C=O)=CC=NC2=C1 MGCGJBXTNWUHQE-UHFFFAOYSA-N 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000001680 trimethoxyphenyl group Chemical group 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- 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
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- 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
-
- 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
- A61P9/06—Antiarrhythmics
-
- 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
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pulmonology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782847236 DE2847236A1 (de) | 1978-10-31 | 1978-10-31 | Neue dihydropyridine mit substituierten estergruppierungen, mehrer verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| US06/083,884 US4551467A (en) | 1978-10-31 | 1979-10-11 | Vasodilating cyanoalkyl esters of 1,4-dihydropyridines |
| AT79104045T ATE1238T1 (de) | 1978-10-31 | 1979-10-19 | Neue 1,4-dihydropyridinverbindungen, verfahren zu ihrer herstellung, die genannten verbindungen enthaltende arzneimittel und verfahren zur herstellung dieser arzneimittel. |
| DE7979104045T DE2963183D1 (en) | 1978-10-31 | 1979-10-19 | 1,4-dihydropyridine compounds, their preparation, pharmaceutical compositions containing said compounds and preparation of these compositions |
| EP79104045A EP0012180B1 (de) | 1978-10-31 | 1979-10-19 | Neue 1,4-Dihydropyridinverbindungen, Verfahren zu ihrer Herstellung, die genannten Verbindungen enthaltende Arzneimittel und Verfahren zur Herstellung dieser Arzneimittel |
| JP13883679A JPS5564571A (en) | 1978-10-31 | 1979-10-29 | Novel 1*44dihydropyridine compound having substituted ester group |
| ES485540A ES485540A1 (es) | 1978-10-31 | 1979-10-30 | Procedimiento para la obtencion de 1,4-dihidropiridinas, congrupos ester funcionalizados |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782847236 DE2847236A1 (de) | 1978-10-31 | 1978-10-31 | Neue dihydropyridine mit substituierten estergruppierungen, mehrer verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2847236A1 true DE2847236A1 (de) | 1980-05-14 |
Family
ID=6053510
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19782847236 Withdrawn DE2847236A1 (de) | 1978-10-31 | 1978-10-31 | Neue dihydropyridine mit substituierten estergruppierungen, mehrer verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| DE7979104045T Expired DE2963183D1 (en) | 1978-10-31 | 1979-10-19 | 1,4-dihydropyridine compounds, their preparation, pharmaceutical compositions containing said compounds and preparation of these compositions |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE7979104045T Expired DE2963183D1 (en) | 1978-10-31 | 1979-10-19 | 1,4-dihydropyridine compounds, their preparation, pharmaceutical compositions containing said compounds and preparation of these compositions |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4551467A (en, 2012) |
| EP (1) | EP0012180B1 (en, 2012) |
| JP (1) | JPS5564571A (en, 2012) |
| AT (1) | ATE1238T1 (en, 2012) |
| DE (2) | DE2847236A1 (en, 2012) |
| ES (1) | ES485540A1 (en, 2012) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0052300A1 (de) * | 1980-11-13 | 1982-05-26 | Bayer Ag | C-3 verknüpfte 1,4-Dihydropyridine, ihre Verwendung in Arzneimitteln und Verfahren zu ihrer Herstellung |
| EP0042089A3 (en) * | 1980-06-12 | 1982-09-22 | Bayer Ag | 4-heterocylic substituted dihydropyridines, processes for preparing them, their therapeutical use and their preparation |
| DE3238705A1 (de) * | 1981-10-19 | 1983-07-14 | Maruko Seiyaku Co. Ltd., Nagoya, Aichi | 1,4-dihydropyridine und diese enthaltende arzneimittel |
| EP0116708A1 (de) * | 1982-12-20 | 1984-08-29 | CASSELLA Aktiengesellschaft | Neue substituierte 1,4-Dihydropyridine, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| US4472411A (en) * | 1982-04-22 | 1984-09-18 | Taisho Pharmaceutical Co., Ltd. | 1,4-Dihydropyridine derivatives and use as vasodilators |
| WO1986001206A1 (en) * | 1984-08-14 | 1986-02-27 | Kowa Co., Ltd. | Novel 1,4-dihidropyridine-3,5-dicarboxylate derivatives |
| EP0199238A1 (de) * | 1985-04-25 | 1986-10-29 | Bayer Ag | 1,4-Dihydropyridin-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung in Arzneimitteln |
| US4622332A (en) * | 1982-03-10 | 1986-11-11 | Bayer Aktiengesellschaft | Asymmetric diesters of Hantzsch dihydropyridines with hypotensive activity |
| EP0595166A1 (de) * | 1992-10-30 | 1994-05-04 | Bayer Ag | 4-Heterocyclyl substituierte Dihydropyridine |
| US6001857A (en) * | 1992-10-30 | 1999-12-14 | Bayer Aktiengesellschaft | Heterocyclyl substituted dihydropyridines |
| CN102796502A (zh) * | 2012-09-11 | 2012-11-28 | 西华师范大学 | 缓蚀剂溴化-n-烷基吡啶丙烯酸酯及其制备方法 |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| JPS58216158A (ja) * | 1982-06-08 | 1983-12-15 | Yoshitomi Pharmaceut Ind Ltd | １，４−ジヒドロピリジン誘導体又はその塩類 |
| US4656181A (en) * | 1982-11-24 | 1987-04-07 | Cermol S.A. | Esters of 1,4-dihydropyridines, processes for the preparation of the new esters, and medicaments containing the same |
| DE3244178A1 (de) * | 1982-11-30 | 1984-05-30 | Bayer Ag, 5090 Leverkusen | 1,4-dihydropyridinderivate, verfahren zu ihrer herstellung sowie ihre verwendung in arzneimitteln |
| JPS6097955A (ja) * | 1983-11-01 | 1985-05-31 | Teijin Ltd | １，４−ジヒドロピリジン−３，５−ジカルボン酸ジエステル誘導体の製造法 |
| DE4342196A1 (de) * | 1993-12-10 | 1995-06-14 | Bayer Ag | Neue 4-Phenyl-substituierte 1,4-Dihydropyridine |
| US4637930A (en) * | 1984-02-08 | 1987-01-20 | Yamanouchi Pharmaceutical Co, Ltd. | Transdermal formulation of nicardipine hydrochloride |
| IE57810B1 (en) * | 1984-03-27 | 1993-04-21 | Delagrange Lab | 1,4-dihydropyridine derivatives,their preparation and their use |
| GB8413385D0 (en) * | 1984-05-24 | 1984-06-27 | Recordati Chem Pharm | Carboxylic acid derivatives |
| DE3431152A1 (de) * | 1984-08-24 | 1986-03-06 | Cassella Ag, 6000 Frankfurt | Verfahren zur herstellung optisch aktiver, substituierter 1,4-dihydropyridine und ihre verwendung als arzneimittel |
| JPS6157556A (ja) * | 1984-08-29 | 1986-03-24 | Teijin Ltd | １，４−ジヒドロピリジン誘導体その製造法およびそれを有効成分とする薬剤 |
| DK8602336A (en, 2012) * | 1985-05-21 | 1986-11-22 | ||
| US4780538A (en) * | 1986-02-12 | 1988-10-25 | Merck & Co., Inc. | Process for 1,4-dihydropyridine compounds using a titanamine catalyst |
| IT1204461B (it) * | 1986-02-20 | 1989-03-01 | Glaxo Spa | Derivati eterociclici |
| JPS62292757A (ja) * | 1986-06-12 | 1987-12-19 | Taisho Pharmaceut Co Ltd | １，４−ジヒドロピリジン誘導体 |
| US5470982A (en) * | 1988-01-20 | 1995-11-28 | Bayer Aktiengesellschaft | Disubstituted pyridines |
| US5234821A (en) * | 1990-09-01 | 1993-08-10 | Kazuo Achiwa | Process for preparing 1,4 dihydropyridine compounds |
| JPH0641075A (ja) | 1990-09-01 | 1994-02-15 | Kazuo Achinami | 新規な１，４−ジヒドロピリジン化合物及びその製造方法 |
| SE9303657D0 (sv) * | 1993-11-05 | 1993-11-05 | Astra Ab | Short-acting dihydropyridines |
| DE4342193A1 (de) * | 1993-12-10 | 1995-06-14 | Bayer Ag | Arylsubstituierte Alkoxycarbonyl-1,4-dihydropyridin-5-carbonsäureester |
| CN103739542B (zh) * | 2013-12-06 | 2018-10-12 | 威海迪素制药有限公司 | 3-(2-腈乙基)-5-甲基-2,6-二甲基-4-(3-硝基苯基)-1,4-二氢吡啶-3,5-二羧酸酯的制备方法 |
| CN115850158B (zh) * | 2022-11-03 | 2025-06-06 | 成都硕德药业有限公司 | 一种地平类药物中间体m2的制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2210672C3 (de) * | 1972-03-06 | 1980-03-20 | Bayer Ag, 5090 Leverkusen | N-substituierte unsymmetrische 1 ^-Dihydropyridin-S^-dicarbonsäureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel |
| US3974275A (en) * | 1972-04-18 | 1976-08-10 | Bayer Aktiengesellschaft | 1,4-Dihydropyridine carboxylic acid esters useful as coronary vessel dilators and anti-hypertensives |
| DE2228363A1 (de) * | 1972-06-10 | 1974-01-03 | Bayer Ag | 1,4-dihydropyridine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| US3966946A (en) * | 1973-06-12 | 1976-06-29 | Smith Kline & French Laboratories Limited | 1,4-Dihydropyridine compounds in treating hypertension |
| DE2508181A1 (de) * | 1975-02-26 | 1976-09-09 | Bayer Ag | 1,4-dihydropyridincarbonsaeurearal- kylester, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| US4284634A (en) * | 1975-07-02 | 1981-08-18 | Fujisawa Pharmaceutical Co., Ltd. | 1,4-Dihydropyridine derivatives, and pharmaceutical method of the same |
| US4307103A (en) * | 1978-09-08 | 1981-12-22 | Fujisawa Pharmaceutical Co., Ltd. | Dihydropyridine derivative, processes for preparation thereof and pharmaceutical composition comprising the same |
-
1978
- 1978-10-31 DE DE19782847236 patent/DE2847236A1/de not_active Withdrawn
-
1979
- 1979-10-11 US US06/083,884 patent/US4551467A/en not_active Expired - Lifetime
- 1979-10-19 EP EP79104045A patent/EP0012180B1/de not_active Expired
- 1979-10-19 AT AT79104045T patent/ATE1238T1/de not_active IP Right Cessation
- 1979-10-19 DE DE7979104045T patent/DE2963183D1/de not_active Expired
- 1979-10-29 JP JP13883679A patent/JPS5564571A/ja active Granted
- 1979-10-30 ES ES485540A patent/ES485540A1/es not_active Expired
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0042089A3 (en) * | 1980-06-12 | 1982-09-22 | Bayer Ag | 4-heterocylic substituted dihydropyridines, processes for preparing them, their therapeutical use and their preparation |
| EP0052300A1 (de) * | 1980-11-13 | 1982-05-26 | Bayer Ag | C-3 verknüpfte 1,4-Dihydropyridine, ihre Verwendung in Arzneimitteln und Verfahren zu ihrer Herstellung |
| DE3238705A1 (de) * | 1981-10-19 | 1983-07-14 | Maruko Seiyaku Co. Ltd., Nagoya, Aichi | 1,4-dihydropyridine und diese enthaltende arzneimittel |
| US4622332A (en) * | 1982-03-10 | 1986-11-11 | Bayer Aktiengesellschaft | Asymmetric diesters of Hantzsch dihydropyridines with hypotensive activity |
| US4472411A (en) * | 1982-04-22 | 1984-09-18 | Taisho Pharmaceutical Co., Ltd. | 1,4-Dihydropyridine derivatives and use as vasodilators |
| EP0116708A1 (de) * | 1982-12-20 | 1984-08-29 | CASSELLA Aktiengesellschaft | Neue substituierte 1,4-Dihydropyridine, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| US4558058A (en) * | 1982-12-20 | 1985-12-10 | Cassella Aktiengesellschaft | Substituted 1,4-dihydropyridines and their use as medicaments |
| WO1986001206A1 (en) * | 1984-08-14 | 1986-02-27 | Kowa Co., Ltd. | Novel 1,4-dihidropyridine-3,5-dicarboxylate derivatives |
| EP0199238A1 (de) * | 1985-04-25 | 1986-10-29 | Bayer Ag | 1,4-Dihydropyridin-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung in Arzneimitteln |
| EP0595166A1 (de) * | 1992-10-30 | 1994-05-04 | Bayer Ag | 4-Heterocyclyl substituierte Dihydropyridine |
| US5502064A (en) * | 1992-10-30 | 1996-03-26 | Bayer Aktiengesellschaft | 4-heterocyclyl-substituted dihydropyridines |
| US6001857A (en) * | 1992-10-30 | 1999-12-14 | Bayer Aktiengesellschaft | Heterocyclyl substituted dihydropyridines |
| CN102796502A (zh) * | 2012-09-11 | 2012-11-28 | 西华师范大学 | 缓蚀剂溴化-n-烷基吡啶丙烯酸酯及其制备方法 |
| CN102796502B (zh) * | 2012-09-11 | 2014-02-19 | 西华师范大学 | 缓蚀剂溴化-n-烷基吡啶丙烯酸酯及其制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0012180B1 (de) | 1982-06-23 |
| US4551467A (en) | 1985-11-05 |
| JPS6241505B2 (en, 2012) | 1987-09-03 |
| ES485540A1 (es) | 1980-05-16 |
| DE2963183D1 (en) | 1982-08-12 |
| JPS5564571A (en) | 1980-05-15 |
| ATE1238T1 (de) | 1982-07-15 |
| EP0012180A1 (de) | 1980-06-25 |
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Legal Events
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| 8130 | Withdrawal |