DE2218644C3 - Basische Ester von 1,4-Dihydropyridinen, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel - Google Patents
Basische Ester von 1,4-Dihydropyridinen, Verfahren zu ihrer Herstellung sowie ihre Verwendung als ArzneimittelInfo
- Publication number
- DE2218644C3 DE2218644C3 DE2218644A DE2218644A DE2218644C3 DE 2218644 C3 DE2218644 C3 DE 2218644C3 DE 2218644 A DE2218644 A DE 2218644A DE 2218644 A DE2218644 A DE 2218644A DE 2218644 C3 DE2218644 C3 DE 2218644C3
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- coo
- meaning given
- general
- given above
- 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
Links
- 238000000034 method Methods 0.000 title claims description 13
- 230000008569 process Effects 0.000 title claims description 6
- 150000002148 esters Chemical class 0.000 title description 10
- 239000003814 drug Substances 0.000 title description 8
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical class C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 title description 6
- 238000002360 preparation method Methods 0.000 title description 2
- -1 dihydropyridine carboxylic acid esters Chemical class 0.000 claims description 16
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 12
- 239000003960 organic solvent Substances 0.000 claims description 10
- 150000001299 aldehydes Chemical class 0.000 claims description 8
- 150000002081 enamines Chemical class 0.000 claims description 8
- 229910021529 ammonia Inorganic materials 0.000 claims description 6
- 150000003863 ammonium salts Chemical class 0.000 claims description 6
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 6
- 229930195729 fatty acid Natural products 0.000 claims description 6
- 239000000194 fatty acid Substances 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- CUNSUQKHHZVKMU-UHFFFAOYSA-N 1,4-dihydropyridine-2-carboxylic acid Chemical class OC(=O)C1=CCC=CN1 CUNSUQKHHZVKMU-UHFFFAOYSA-N 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000002955 isolation Methods 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 1
- WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical compound CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 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 13
- 150000004702 methyl esters Chemical class 0.000 description 11
- 239000013078 crystal Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 239000002253 acid Substances 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 230000009471 action Effects 0.000 description 5
- 230000002490 cerebral effect Effects 0.000 description 5
- 210000003748 coronary sinus Anatomy 0.000 description 5
- CMWKITSNTDAEDT-UHFFFAOYSA-N 2-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC=C1C=O CMWKITSNTDAEDT-UHFFFAOYSA-N 0.000 description 4
- 241000282472 Canis lupus familiaris Species 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- 230000003727 cerebral blood flow Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 150000003840 hydrochlorides Chemical class 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 210000004731 jugular vein Anatomy 0.000 description 3
- 229910052724 xenon Inorganic materials 0.000 description 3
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 3
- BCVBBQMUAAFVJC-UHFFFAOYSA-N 1,2,3,4-tetrahydropyridin-1-ium-2-carboxylate Chemical class OC(=O)C1CCC=CN1 BCVBBQMUAAFVJC-UHFFFAOYSA-N 0.000 description 2
- FHPBHRZTBMGASR-UHFFFAOYSA-N 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine Chemical compound C1=C(C)NC(C)=CC1C1=CC=CC=C1[N+]([O-])=O FHPBHRZTBMGASR-UHFFFAOYSA-N 0.000 description 2
- ZDVRPKUWYQVVDX-UHFFFAOYSA-N 2-(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC=CC=C1C=O ZDVRPKUWYQVVDX-UHFFFAOYSA-N 0.000 description 2
- NHTBGGLIHGSCFA-UHFFFAOYSA-N 2-azidobenzaldehyde Chemical compound [N-]=[N+]=NC1=CC=CC=C1C=O NHTBGGLIHGSCFA-UHFFFAOYSA-N 0.000 description 2
- ZETIVVHRRQLWFW-UHFFFAOYSA-N 3-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC(C=O)=C1 ZETIVVHRRQLWFW-UHFFFAOYSA-N 0.000 description 2
- BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 210000004781 brain capillary Anatomy 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 210000004351 coronary vessel Anatomy 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 210000002460 smooth muscle Anatomy 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- 230000002792 vascular Effects 0.000 description 2
- RXPRRQLKFXBCSJ-GIVPXCGWSA-N vincamine Chemical compound C1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)C[C@](O)(C(=O)OC)N5C2=C1 RXPRRQLKFXBCSJ-GIVPXCGWSA-N 0.000 description 2
- PAWSVPVNIXFKOS-IHWYPQMZSA-N (Z)-2-aminobutenoic acid Chemical compound C\C=C(/N)C(O)=O PAWSVPVNIXFKOS-IHWYPQMZSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RMZQSAMHIQBMLW-UHFFFAOYSA-N 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid Chemical compound OC(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC=C1[N+]([O-])=O RMZQSAMHIQBMLW-UHFFFAOYSA-N 0.000 description 1
- NCHLDZALJLMLPJ-UHFFFAOYSA-N 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine Chemical compound C1=C(C)NC(C)=CC1C1=CC=CC([N+]([O-])=O)=C1 NCHLDZALJLMLPJ-UHFFFAOYSA-N 0.000 description 1
- AWZSDBLQPOCXKG-UHFFFAOYSA-N 2,6-dimethyl-4-(4-nitrophenyl)-1,4-dihydropyridine Chemical compound CC=1NC(=CC(C=1)C1=CC=C(C=C1)[N+](=O)[O-])C AWZSDBLQPOCXKG-UHFFFAOYSA-N 0.000 description 1
- FEOAIYBLDKAOFS-UHFFFAOYSA-N 2,6-dimethyl-4-phenyl-1,4-dihydropyridine Chemical compound C1=C(C)NC(C)=CC1C1=CC=CC=C1 FEOAIYBLDKAOFS-UHFFFAOYSA-N 0.000 description 1
- NMTUHPSKJJYGML-UHFFFAOYSA-N 3-(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC=CC(C=O)=C1 NMTUHPSKJJYGML-UHFFFAOYSA-N 0.000 description 1
- UCJDGRYGBYCWMS-UHFFFAOYSA-N 3-azidobenzaldehyde Chemical compound [N-]=[N+]=NC1=CC=CC(C=O)=C1 UCJDGRYGBYCWMS-UHFFFAOYSA-N 0.000 description 1
- BEOBZEOPTQQELP-UHFFFAOYSA-N 4-(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC=C(C=O)C=C1 BEOBZEOPTQQELP-UHFFFAOYSA-N 0.000 description 1
- SDJOUGYEUFYPLL-UHFFFAOYSA-N 4-azidobenzaldehyde Chemical compound [N-]=[N+]=NC1=CC=C(C=O)C=C1 SDJOUGYEUFYPLL-UHFFFAOYSA-N 0.000 description 1
- 206010001497 Agitation Diseases 0.000 description 1
- REIYHFWZISXFKU-UHFFFAOYSA-N Butyl acetoacetate Chemical compound CCCCOC(=O)CC(C)=O REIYHFWZISXFKU-UHFFFAOYSA-N 0.000 description 1
- HREYLINMENLFJE-UHFFFAOYSA-N CC(NC(C)=C1)=CC1C(C=CC=C1)=C1N=[N+]=[N-] Chemical compound CC(NC(C)=C1)=CC1C(C=CC=C1)=C1N=[N+]=[N-] HREYLINMENLFJE-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 206010052804 Drug tolerance Diseases 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- RLKBOGLIOLFMEK-NSCUHMNNSA-N amino (e)-but-2-enoate Chemical compound C\C=C\C(=O)ON RLKBOGLIOLFMEK-NSCUHMNNSA-N 0.000 description 1
- 230000003440 anti-fibrillation Effects 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- DERZBLKQOCDDDZ-JLHYYAGUSA-N cinnarizine Chemical compound C1CN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CCN1C\C=C\C1=CC=CC=C1 DERZBLKQOCDDDZ-JLHYYAGUSA-N 0.000 description 1
- 229960000876 cinnarizine Drugs 0.000 description 1
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- RXPRRQLKFXBCSJ-UHFFFAOYSA-N dl-Vincamin Natural products C1=CC=C2C(CCN3CCC4)=C5C3C4(CC)CC(O)(C(=O)OC)N5C2=C1 RXPRRQLKFXBCSJ-UHFFFAOYSA-N 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000026781 habituation Effects 0.000 description 1
- 210000003128 head Anatomy 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- CJBFCOOECPQZDM-VOTSOKGWSA-N methyl (e)-5-(2-nitrophenyl)-3-oxopent-4-enoate Chemical compound COC(=O)CC(=O)\C=C\C1=CC=CC=C1[N+]([O-])=O CJBFCOOECPQZDM-VOTSOKGWSA-N 0.000 description 1
- VCDOXKMVZZSCQK-ARJAWSKDSA-N methyl (z)-2-aminobut-2-enoate Chemical compound COC(=O)C(\N)=C\C VCDOXKMVZZSCQK-ARJAWSKDSA-N 0.000 description 1
- FCRJJPWNWLNCPA-UHFFFAOYSA-N methyl 3-oxo-5-phenylpent-4-enoate Chemical compound COC(=O)CC(=O)C=CC1=CC=CC=C1 FCRJJPWNWLNCPA-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 230000003387 muscular Effects 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- JEMFYCFWXQJCPM-XQRVVYSFSA-N propan-2-yl (z)-2-aminobut-2-enoate Chemical compound C\C=C(/N)C(=O)OC(C)C JEMFYCFWXQJCPM-XQRVVYSFSA-N 0.000 description 1
- GVIIRWAJDFKJMJ-UHFFFAOYSA-N propan-2-yl 3-oxobutanoate Chemical compound CC(C)OC(=O)CC(C)=O GVIIRWAJDFKJMJ-UHFFFAOYSA-N 0.000 description 1
- DHGFMVMDBNLMKT-UHFFFAOYSA-N propyl 3-oxobutanoate Chemical compound CCCOC(=O)CC(C)=O DHGFMVMDBNLMKT-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 210000004761 scalp Anatomy 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 230000003235 vasospasmolytic effect Effects 0.000 description 1
- 229960002726 vincamine Drugs 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
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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
- A61P11/08—Bronchodilators
-
- 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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- 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
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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
- A61P9/12—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
-
- 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
- C07D401/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical 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)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Pulmonology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Pyridine Compounds (AREA)
Priority Applications (48)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2218644A DE2218644C3 (de) | 1972-04-18 | 1972-04-18 | Basische Ester von 1,4-Dihydropyridinen, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel |
| US350381A US3905970A (en) | 1972-04-18 | 1973-04-12 | 1,4-Dihydropyridine carboxylic acid esters |
| AU54491/73A AU467406B2 (en) | 1972-04-18 | 1973-04-13 | NEW, l, 4-DIHYDROPYRIDINE CARBOXYLIC ACID COMPOUNDS, THEIR PRODUCTION, AND THEIR MEDICINAL USE |
| DD170202A DD107275A5 (OSRAM) | 1972-04-18 | 1973-04-16 | |
| AT45875*7A AT329559B (de) | 1972-04-18 | 1973-04-16 | Verfahren zur herstellung neuer basischer ester von 1,4-dihydropyridinen |
| JP4225373A JPS5637225B2 (OSRAM) | 1972-04-18 | 1973-04-16 | |
| AT45775*A ATA45775A (de) | 1972-04-18 | 1973-04-16 | Verfahren zur herstellung neuer basischer ester von 1,4-dihydropyridinen |
| AT45975*A ATA45975A (de) | 1972-04-18 | 1973-04-16 | Verfahren zur herstellung neuer basischer ester von 1,4-dihydropyridinen |
| AT337373A AT327191B (de) | 1972-04-18 | 1973-04-16 | Verfahren zur herstellung neuer basischer ester von 1,4-dihydropyridinen |
| CA168,760A CA1006515A (en) | 1972-04-18 | 1973-04-16 | 1,4-dihydropyridine carboxylic acid esters |
| SU1911372A SU518127A3 (ru) | 1972-04-18 | 1973-04-16 | Способ получени основных сложных эфиров 1,4-дигидропиридинкарбоновой кислоты или их солей |
| AT45775*7A AT327905B (de) | 1972-04-18 | 1973-04-16 | Verfahren zur herstellung neuer basischer ester von 1,4-dihydropyridinen |
| FI1193/73A FI55997C (fi) | 1972-04-18 | 1973-04-16 | Foerfarande foer framstaellning av terapeutiskt aktiva 1,4-dihydrokarboxylsyraestrar |
| IL42044A IL42044A (en) | 1972-04-18 | 1973-04-16 | 1,4-dihydropyridine carboxylic acid esters,their production and pharmaceutical compositions containing them |
| AT45875*A ATA45875A (de) | 1972-04-18 | 1973-04-16 | Verfahren zur herstellung neuer basischer ester von 1,4-dihydropyridinen |
| AT45975*7A AT329560B (de) | 1972-04-18 | 1973-04-16 | Verfahren zur herstellung neuer basischer ester von 1,4-dihydropyridinen |
| JP48042254A JPS4914614A (OSRAM) | 1972-04-18 | 1973-04-16 | |
| CS6249A CS174250B2 (OSRAM) | 1972-04-18 | 1973-04-17 | |
| CH319476A CH591446A5 (OSRAM) | 1972-04-18 | 1973-04-17 | |
| IE604/73A IE37538B1 (en) | 1972-04-18 | 1973-04-17 | New 1,4-dihydropyridine carboxylic acid compounds their production and their medicinal use |
| DK208973A DK137753C (da) | 1972-04-18 | 1973-04-17 | Analogifremgangsmaade til fremstilling af basiske 1,4-dihydropyridincarboxylsyreestere |
| CH319276A CH591445A5 (OSRAM) | 1972-04-18 | 1973-04-17 | |
| ES413809A ES413809A1 (es) | 1972-04-18 | 1973-04-17 | Procedimiento para la obtencion de esteres basicos de acido1,4-dihidropiridincarboxilico. |
| CS6245A CS174246B2 (OSRAM) | 1972-04-18 | 1973-04-17 | |
| CH319176A CH590842A5 (OSRAM) | 1972-04-18 | 1973-04-17 | |
| CS2764A CS174201B2 (OSRAM) | 1972-04-18 | 1973-04-17 | |
| SE7305462A SE398876B (sv) | 1972-04-18 | 1973-04-17 | Sett att framstella basiska 1,4-dihydropyridinkarbonsyraestrar |
| CH319076A CH590841A5 (OSRAM) | 1972-04-18 | 1973-04-17 | |
| CS6246A CS174247B2 (OSRAM) | 1972-04-18 | 1973-04-17 | |
| ZA732633A ZA732633B (en) | 1972-04-18 | 1973-04-17 | New 1,4-dihydropyridine carboxylic acid compounds,their production,and their medical use |
| CS6247A CS174248B2 (OSRAM) | 1972-04-18 | 1973-04-17 | |
| CH554373A CH589627A5 (OSRAM) | 1972-04-18 | 1973-04-17 | |
| CH319376A CH588464A5 (OSRAM) | 1972-04-18 | 1973-04-17 | |
| CS6248A CS174249B2 (OSRAM) | 1972-04-18 | 1973-04-17 | |
| GB1872573A GB1383625A (en) | 1972-04-18 | 1973-04-18 | 1,4-dihydropyridine carboxylic acid compounds their production and their medicinal use |
| BE130166A BE798403A (fr) | 1972-04-18 | 1973-04-18 | Esters basiques d'acides 1,4-dihydropyridine-carboxyliques et leur obtention |
| FR7314175A FR2182983B1 (OSRAM) | 1972-04-18 | 1973-04-18 | |
| HUBA2916A HU167989B (OSRAM) | 1972-04-18 | 1973-04-18 | |
| NLAANVRAGE7305479,A NL176942C (nl) | 1972-04-18 | 1973-04-18 | Werkwijze voor het bereiden van farmaceutische preparaten met ten minste een 2,6-dimethyl 3,5-dicarbonzuurester 4-(gesubstitueerd fenyl) 1,4-dihydropyridine als werkzame verbinding alsmede werkwijze ter bereiding van die werkzame verbindingen. |
| SU2032539A SU516351A3 (ru) | 1972-04-18 | 1974-06-13 | Способ получени сложных эфиров 1,4-дигидропиридинкарбоновой кислоты или их солей |
| SU2032541A SU516352A3 (ru) | 1972-04-18 | 1974-06-13 | Способ получени сложных эфиров 1,4-дигидропиридинкарбоновой кислоты или их солей |
| SU2032542A SU513621A3 (ru) | 1972-04-18 | 1974-06-13 | Способ получени сложных эфиров 1,4-дигидропиридинкарбоновой кислоты или их солей |
| SU2032538A SU515452A3 (ru) | 1972-04-18 | 1974-06-13 | Способ получени сложных эфиров 1,4-дигидропиридинкарбоновой кислоты или их солей |
| SU2032540A SU513620A3 (ru) | 1972-04-18 | 1974-06-13 | Способ получени сложных эфиров 1,4-дигидропиридинкарбоновой кислоты или их солей |
| US05/548,394 US3996234A (en) | 1972-04-18 | 1975-02-10 | 1,4-Dihydropyridine carboxylic acid esters |
| US05/548,395 US3974275A (en) | 1972-04-18 | 1975-02-10 | 1,4-Dihydropyridine carboxylic acid esters useful as coronary vessel dilators and anti-hypertensives |
| US05/631,119 US4031104A (en) | 1972-04-18 | 1975-11-12 | 1,4-Dihydropyridine carboxylic acid esters |
| US05/647,414 US4038399A (en) | 1972-04-18 | 1976-01-08 | 1,4-dihydropyridine carboxylic acid esters useful as coronary vessel dilators and anti-hypertensives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2218644A DE2218644C3 (de) | 1972-04-18 | 1972-04-18 | Basische Ester von 1,4-Dihydropyridinen, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2218644A1 DE2218644A1 (de) | 1973-10-25 |
| DE2218644B2 DE2218644B2 (de) | 1980-04-30 |
| DE2218644C3 true DE2218644C3 (de) | 1982-08-19 |
Family
ID=5842285
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2218644A Expired DE2218644C3 (de) | 1972-04-18 | 1972-04-18 | Basische Ester von 1,4-Dihydropyridinen, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US3905970A (OSRAM) |
| JP (2) | JPS5637225B2 (OSRAM) |
| AT (7) | ATA45975A (OSRAM) |
| AU (1) | AU467406B2 (OSRAM) |
| BE (1) | BE798403A (OSRAM) |
| CA (1) | CA1006515A (OSRAM) |
| CH (6) | CH590841A5 (OSRAM) |
| CS (6) | CS174250B2 (OSRAM) |
| DD (1) | DD107275A5 (OSRAM) |
| DE (1) | DE2218644C3 (OSRAM) |
| DK (1) | DK137753C (OSRAM) |
| ES (1) | ES413809A1 (OSRAM) |
| FI (1) | FI55997C (OSRAM) |
| FR (1) | FR2182983B1 (OSRAM) |
| GB (1) | GB1383625A (OSRAM) |
| HU (1) | HU167989B (OSRAM) |
| IE (1) | IE37538B1 (OSRAM) |
| IL (1) | IL42044A (OSRAM) |
| NL (1) | NL176942C (OSRAM) |
| SE (1) | SE398876B (OSRAM) |
| SU (6) | SU518127A3 (OSRAM) |
| ZA (1) | ZA732633B (OSRAM) |
Families Citing this family (63)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4038399A (en) * | 1972-04-18 | 1977-07-26 | Bayer Aktiengesellschaft | 1,4-dihydropyridine carboxylic acid esters useful as coronary vessel dilators and anti-hypertensives |
| FR2218107A1 (en) * | 1973-02-20 | 1974-09-13 | Yamanouchi Pharma Co Ltd | Amino alkyl 2,6-dialkyl-4-aryl-1,4 dihydropyridine-3, carboxylates - useful as cerebral vasodilators and musculotropic spasmolytic agents |
| US3985758A (en) * | 1973-02-20 | 1976-10-12 | Yamanouchi Pharmaceutical Co., Ltd. | 1,4-Dihydropyridine derivatives |
| DE2508181A1 (de) * | 1975-02-26 | 1976-09-09 | Bayer Ag | 1,4-dihydropyridincarbonsaeurearal- kylester, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| FR2320750A1 (fr) * | 1975-08-12 | 1977-03-11 | Hexachimie | Dihydro-1,4 pyridines et leur application therapeutique |
| DE2738153A1 (de) * | 1977-08-24 | 1979-03-08 | Bayer Ag | 2-pyridyl-1,4-dihydropyridine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| JPS55301A (en) * | 1978-02-14 | 1980-01-05 | Yamanouchi Pharmaceut Co Ltd | 1,4-dihydropyridine-3,5-dicarboxylic ester derivative and its preparation |
| DE2847237A1 (de) * | 1978-10-31 | 1980-05-14 | Bayer Ag | Verfahren zur herstellung von 1,4-dihydropyridincarbonsaeuren sowie ihre verwendung als arzneimittel |
| US4285955A (en) * | 1978-10-31 | 1981-08-25 | Bayer Aktiengesellschaft | 1,4-Dihydropyridinecarboxylic acids |
| DE2949464A1 (de) * | 1978-12-18 | 1980-06-26 | Sandoz Ag | Benzoxadiazole und benzothiadiazole, ihre herstellung und verwendung |
| JPS57171968A (en) * | 1981-04-17 | 1982-10-22 | Kyowa Hakko Kogyo Co Ltd | 1,4-dihydropyridine derivative |
| JPS57200386A (en) * | 1981-06-04 | 1982-12-08 | Yoshitomi Pharmaceut Ind Ltd | Novel 1,4-dihydropyridine-3,5-dicarboxylic ester derivative and its salts |
| NZ201395A (en) * | 1981-07-30 | 1987-02-20 | Bayer Ag | Pharmaceutical compositions containing 1,4-dihydropyridines and certain of these dihydropyridines |
| JPS58131982A (ja) * | 1982-02-01 | 1983-08-06 | Tokyo Tanabe Co Ltd | 新規なる１．４−ジヒドロピリジン誘導体 |
| FR2511370B1 (fr) * | 1981-08-12 | 1986-10-24 | Tokyo Tanabe Co | Derives de 1,4-dihydropyridine a activite vasodilatatrice et d'hypotension |
| JPS58159490A (ja) * | 1982-02-23 | 1983-09-21 | Nikken Kagaku Kk | １，４−ジヒドロピリジン化合物 |
| 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. |
| JPS58201765A (ja) * | 1982-05-10 | 1983-11-24 | Takeda Chem Ind Ltd | ジヒドロピリジン誘導体，その製造法および用途 |
| 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 |
| US4419518A (en) * | 1982-07-26 | 1983-12-06 | Tokyo Tanabe Co. L.T.D. | 1,4-Dihydropyridine derivatives |
| PH19166A (en) * | 1982-09-04 | 1986-01-16 | Pfizer | Dihydropyridined,pharmaceutical compositions and method of use |
| JPS5951281A (ja) * | 1982-09-17 | 1984-03-24 | Yoshitomi Pharmaceut Ind Ltd | １，４−ジヒドロピリジン−３，５−ジカルボン酸エステル誘導体 |
| DE3234684A1 (de) * | 1982-09-18 | 1984-03-22 | Bayer Ag, 5090 Leverkusen | Neue dihydropyrimidine, verfahren zu ihrer herstellung sowie ihre verwendung in arzneimitteln |
| JPS5970667A (ja) * | 1982-10-15 | 1984-04-21 | Kyowa Hakko Kogyo Co Ltd | １，４−ジヒドロピリジン誘導体 |
| JPS5970666A (ja) * | 1982-10-15 | 1984-04-21 | Kyowa Hakko Kogyo Co Ltd | １，４−ジヒドロピリジン誘導体 |
| JPS59225162A (ja) * | 1983-06-03 | 1984-12-18 | Kyowa Hakko Kogyo Co Ltd | １，４−ジヒドロピリジン誘導体 |
| AU557175B2 (en) * | 1982-10-15 | 1986-12-11 | Kyowa Hakko Kogyo Co. Ltd. | 2,6-dimethyl-4-(3-nitro phenyl)-1,4-dihydro pyridine-3,5- dicarboxylic acid esters |
| 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 |
| US4491582A (en) * | 1983-03-03 | 1985-01-01 | Usv Pharmaceutical Corporation | N-(substituted piperazino)-1,4-dihydropyridine-3,5-carboxylic acid |
| AU561213B2 (en) * | 1983-06-02 | 1987-04-30 | Teijin Limited | 1, 4-dihydropyridine derivative |
| US4603135A (en) * | 1983-10-17 | 1986-07-29 | Takeda Chemical Industries, Ltd. | Substituted piperazinyl alkyl esters of 2-amino-4-aryl-1,4-dihydro-6-alkyl-3,5-pyridinedicarboxylates |
| JPS6092266A (ja) * | 1983-10-27 | 1985-05-23 | 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，その製造法及びそれを有効成分とする薬剤 |
| JPS60120861A (ja) * | 1983-12-02 | 1985-06-28 | Otsuka Pharmaceut Co Ltd | ジヒドロピリジン誘導体 |
| DE4342196A1 (de) * | 1993-12-10 | 1995-06-14 | Bayer Ag | Neue 4-Phenyl-substituierte 1,4-Dihydropyridine |
| 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 |
| IE57810B1 (en) * | 1984-03-27 | 1993-04-21 | Delagrange Lab | 1,4-dihydropyridine derivatives,their preparation and their use |
| US4895846A (en) * | 1984-04-11 | 1990-01-23 | Bristol-Myers Company | Pharmaceutically useful dihydropyridinyldicarboxylate amides and esters incorporating arylpiperazinylalkyl moieties |
| US4755512A (en) * | 1984-04-11 | 1988-07-05 | Bristol-Myers Company | Pharmaceutically useful dihydropyridinyldicarboxylate amides and esters incorporating arylpiperazinylalkyl moities |
| AU587393B2 (en) * | 1984-08-03 | 1989-08-17 | Mitsui & Co., Ltd. | Freezing food in brine |
| JPS6147477A (ja) * | 1984-08-14 | 1986-03-07 | Kowa Co | 新規１，４−ジヒドロピリジン−３，５−ジカルボン酸エステル誘導体 |
| JPH0676405B2 (ja) * | 1986-06-13 | 1994-09-28 | 日清製粉株式会社 | １，４―ジヒドロピリジン誘導体およびそれを含有する医薬組成物 |
| US4757071A (en) * | 1984-12-14 | 1988-07-12 | Nisshin Flour Milling Co., Ltd. | 1,4-dihydropyridine derivatives, and pharmaceutical compositions containing same, useful for treating cardiovascular diseases |
| US4833150A (en) * | 1985-03-14 | 1989-05-23 | Nelson Research & Development Co. | 1,4-dihydropyridines |
| US4652573A (en) * | 1985-03-14 | 1987-03-24 | Nelson Research & Development Co. | Calcium antagonist N-hetero ester 1,4-dihydropyridines |
| US4593033A (en) * | 1985-04-24 | 1986-06-03 | Merck & Co., Inc. | Substituted indeno[2,1-c] pyridines useful as calcium channel blockers |
| DK8602336A (OSRAM) * | 1985-05-21 | 1986-11-22 | ||
| US4605660A (en) * | 1985-06-03 | 1986-08-12 | Merck & Co., Inc. | Indeno[2,1-c]pyridine compounds, and their use as calcium channel blockers |
| US4670443A (en) * | 1985-07-02 | 1987-06-02 | Merck & Co., Inc. | Benzo(f)isoquinoline compounds useful as calcium entry blockers |
| DE3682857D1 (en) * | 1985-09-13 | 1992-01-23 | Green Cross Corp | Dihydropyridinderivate. |
| US4735956A (en) * | 1985-09-13 | 1988-04-05 | Merck & Co., Inc. | Certain 1,4-dihydro-2,6-di-lower hydrocarbyl-4-heterocyclic-3,5-pyridine dicarboxylates which are useful as calcium channel blockers |
| IT1201476B (it) * | 1985-10-04 | 1989-02-02 | Yason Srl | Derivato diidropiridinico,procedimento per la sua preparazione e composizioni farmaceutiche che lo contengono |
| US4788203A (en) * | 1985-11-26 | 1988-11-29 | Merck & Co., Inc. | Cyclized N-substituted-tetrahydropyridine compounds, useful in the treatment of cardiovascular disorders |
| US4721708A (en) * | 1985-11-26 | 1988-01-26 | Merck & Co., Inc. | Cyclized N-substituted-tetrahydropyridine compounds and cardiovascular use |
| US4771057A (en) * | 1986-02-03 | 1988-09-13 | University Of Alberta | Reduced pyridyl derivatives with cardiovascular regulating properties |
| US4849436A (en) * | 1986-03-11 | 1989-07-18 | Nelson Research & Development Co. | 1,4-dihydropyridines |
| HU196755B (en) * | 1986-09-16 | 1989-01-30 | Gyogyszerkutato Intezet | Process for production of new substituated amilid derivatives and medical compositions containing them |
| WO1988009331A1 (en) * | 1987-05-22 | 1988-12-01 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Process for manufacturing carboxylic acids |
| DE3732380A1 (de) * | 1987-09-25 | 1989-04-06 | Bayer Ag | Dihydropyridinether, verfahren zu ihrer herstellung und ihre verwendung |
| US5216172A (en) * | 1988-02-24 | 1993-06-01 | Ajinomoto Co., Inc. | 1,4-dihydropyridine-4-aryl-2,6-dimethyl-3,5-dicarboxylates useful as agents against drug resistant tumor cells |
| EP0330470A3 (en) * | 1988-02-24 | 1992-01-02 | Ajinomoto Co., Inc. | 1,4-dihydropyridine derivatives useful against tumour cells |
| US4985558A (en) * | 1988-07-28 | 1991-01-15 | Nikken Chemicals Co., Ltd. | 1,4-dihydropyridine derivative |
| DE4342195A1 (de) * | 1993-12-10 | 1995-06-14 | Bayer Ag | Dihydropyridine mit heterocyclisch substituierten Estern |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1545873A1 (de) * | 1965-11-10 | 1970-02-26 | Bayer Ag | Verfahren zur Herstellung von Dihydrodipyridylderivaten |
| DE1670827C3 (de) * | 1967-03-20 | 1974-10-24 | Bayer Ag, 5090 Leverkusen | 4-(2'-Nitrophenyl)-2,6-dimethyl-3,5-dicarbmethoxy-1,4-dihydropyridin |
| DE1923990C3 (de) * | 1969-05-10 | 1978-11-23 | Bayer Ag | Verfahren zur Herstellung von N-substituierten M-Dihydropyridin-S.S-dicarbonsäureestern |
| DE1963185A1 (de) * | 1969-12-17 | 1971-06-24 | Bayer Ag | Neue Nitrophenyl-1,4-dihydropyridinderivate |
| DE2117571C3 (de) * | 1971-04-10 | 1979-10-11 | Bayer Ag, 5090 Leverkusen | Unsymmetrische 1,4-Dihydropyridin-33-dicarbonsäureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel |
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1972
- 1972-04-18 DE DE2218644A patent/DE2218644C3/de not_active Expired
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1973
- 1973-04-12 US US350381A patent/US3905970A/en not_active Expired - Lifetime
- 1973-04-13 AU AU54491/73A patent/AU467406B2/en not_active Expired
- 1973-04-16 SU SU1911372A patent/SU518127A3/ru active
- 1973-04-16 DD DD170202A patent/DD107275A5/xx unknown
- 1973-04-16 JP JP4225373A patent/JPS5637225B2/ja not_active Expired
- 1973-04-16 AT AT45975*A patent/ATA45975A/de not_active IP Right Cessation
- 1973-04-16 FI FI1193/73A patent/FI55997C/fi active
- 1973-04-16 AT AT45975*7A patent/AT329560B/de not_active IP Right Cessation
- 1973-04-16 JP JP48042254A patent/JPS4914614A/ja active Pending
- 1973-04-16 AT AT45775*7A patent/AT327905B/de not_active IP Right Cessation
- 1973-04-16 AT AT45775*A patent/ATA45775A/de not_active IP Right Cessation
- 1973-04-16 IL IL42044A patent/IL42044A/xx unknown
- 1973-04-16 CA CA168,760A patent/CA1006515A/en not_active Expired
- 1973-04-16 AT AT45875*A patent/ATA45875A/de not_active IP Right Cessation
- 1973-04-16 AT AT337373A patent/AT327191B/de not_active IP Right Cessation
- 1973-04-16 AT AT45875*7A patent/AT329559B/de not_active IP Right Cessation
- 1973-04-17 CH CH319076A patent/CH590841A5/xx not_active IP Right Cessation
- 1973-04-17 CS CS6249A patent/CS174250B2/cs unknown
- 1973-04-17 CH CH319276A patent/CH591445A5/xx not_active IP Right Cessation
- 1973-04-17 CS CS6246A patent/CS174247B2/cs unknown
- 1973-04-17 CH CH319476A patent/CH591446A5/xx not_active IP Right Cessation
- 1973-04-17 ES ES413809A patent/ES413809A1/es not_active Expired
- 1973-04-17 CS CS2764A patent/CS174201B2/cs unknown
- 1973-04-17 ZA ZA732633A patent/ZA732633B/xx unknown
- 1973-04-17 CH CH554373A patent/CH589627A5/xx not_active IP Right Cessation
- 1973-04-17 DK DK208973A patent/DK137753C/da not_active IP Right Cessation
- 1973-04-17 CH CH319376A patent/CH588464A5/xx not_active IP Right Cessation
- 1973-04-17 CS CS6247A patent/CS174248B2/cs unknown
- 1973-04-17 IE IE604/73A patent/IE37538B1/xx unknown
- 1973-04-17 CH CH319176A patent/CH590842A5/xx not_active IP Right Cessation
- 1973-04-17 SE SE7305462A patent/SE398876B/xx unknown
- 1973-04-17 CS CS6248A patent/CS174249B2/cs unknown
- 1973-04-17 CS CS6245A patent/CS174246B2/cs unknown
- 1973-04-18 NL NLAANVRAGE7305479,A patent/NL176942C/xx not_active IP Right Cessation
- 1973-04-18 HU HUBA2916A patent/HU167989B/hu unknown
- 1973-04-18 BE BE130166A patent/BE798403A/xx not_active IP Right Cessation
- 1973-04-18 FR FR7314175A patent/FR2182983B1/fr not_active Expired
- 1973-04-18 GB GB1872573A patent/GB1383625A/en not_active Expired
-
1974
- 1974-06-13 SU SU2032539A patent/SU516351A3/ru active
- 1974-06-13 SU SU2032541A patent/SU516352A3/ru active
- 1974-06-13 SU SU2032538A patent/SU515452A3/ru active
- 1974-06-13 SU SU2032542A patent/SU513621A3/ru active
- 1974-06-13 SU SU2032540A patent/SU513620A3/ru active
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