CS241144B2 - Method of new substituted 1,4-dihydropyridines production - Google Patents
Method of new substituted 1,4-dihydropyridines production Download PDFInfo
- Publication number
- CS241144B2 CS241144B2 CS839613A CS961383A CS241144B2 CS 241144 B2 CS241144 B2 CS 241144B2 CS 839613 A CS839613 A CS 839613A CS 961383 A CS961383 A CS 961383A CS 241144 B2 CS241144 B2 CS 241144B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- oxadiazol
- formula
- acid
- group
- dihydro
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 25
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical class C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title description 3
- -1 alkoxy carbon Chemical compound 0.000 claims description 100
- 150000001875 compounds Chemical class 0.000 claims description 64
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 63
- 239000002253 acid Substances 0.000 claims description 46
- 239000011664 nicotinic acid Substances 0.000 claims description 32
- 235000001968 nicotinic acid Nutrition 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 20
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 18
- 150000002148 esters Chemical class 0.000 claims description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- 239000007858 starting material Substances 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 12
- 125000001495 ethyl group Chemical class [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000001449 isopropyl group Chemical class [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 125000004509 1,3,4-oxadiazol-2-yl group Chemical group O1C(=NN=C1)* 0.000 claims description 8
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 8
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 7
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 6
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000000999 tert-butyl group Chemical class [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 150000002576 ketones Chemical class 0.000 claims description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 150000004702 methyl esters Chemical class 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 150000002825 nitriles Chemical class 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 229920000570 polyether Polymers 0.000 claims description 4
- 150000003462 sulfoxides Chemical class 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical group 0.000 claims description 3
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical class CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 3
- 238000011282 treatment Methods 0.000 claims description 3
- ZVXXPJNJMRONKV-UHFFFAOYSA-N 4-(2,3-dichlorophenyl)-2,6-dimethyl-5-(1,3,4-oxadiazol-2-yl)-1,4-dihydropyridine-3-carboxylic acid Chemical compound CC=1NC(C)=C(C(O)=O)C(C=2C(=C(Cl)C=CC=2)Cl)C=1C1=NN=CO1 ZVXXPJNJMRONKV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- HQZBKFTXHVSRMX-UHFFFAOYSA-N 5-(3-benzyl-1,2,4-oxadiazol-5-yl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid Chemical compound CC=1NC(=C(C(C=1C(=O)O)C1=CC(=CC=C1)[N+](=O)[O-])C1=NC(=NO1)CC1=CC=CC=C1)C HQZBKFTXHVSRMX-UHFFFAOYSA-N 0.000 claims 1
- VAHUDKPPXKGUAE-UHFFFAOYSA-N 5-(3-benzyl-1,2,4-oxadiazol-5-yl)-4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3-carboxylic acid Chemical compound CC=1NC(C)=C(C(O)=O)C(C=2C(=C(Cl)C=CC=2)Cl)C=1C(ON=1)=NC=1CC1=CC=CC=C1 VAHUDKPPXKGUAE-UHFFFAOYSA-N 0.000 claims 1
- VAZRBRBWVRWBPK-UHFFFAOYSA-N CC=1NC(=C(C(C1C(=O)O)C1=CC(=CC=C1)[N+](=O)[O-])C1=NN=CO1)C Chemical compound CC=1NC(=C(C(C1C(=O)O)C1=CC(=CC=C1)[N+](=O)[O-])C1=NN=CO1)C VAZRBRBWVRWBPK-UHFFFAOYSA-N 0.000 claims 1
- IOYNQIMAUDJVEI-BMVIKAAMSA-N Tepraloxydim Chemical group C1C(=O)C(C(=N/OC\C=C\Cl)/CC)=C(O)CC1C1CCOCC1 IOYNQIMAUDJVEI-BMVIKAAMSA-N 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
- 241000755093 Gaidropsarus vulgaris Species 0.000 description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 8
- 239000013543 active substance Substances 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000008298 dragée Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 229920002261 Corn starch Polymers 0.000 description 5
- 239000000969 carrier Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 230000008602 contraction Effects 0.000 description 4
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 4
- 239000000825 pharmaceutical preparation Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000000829 suppository Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 239000001431 2-methylbenzaldehyde Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 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
- 229940127291 Calcium channel antagonist Drugs 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-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
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 230000036772 blood pressure Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000008120 corn starch Substances 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000007903 gelatin capsule Substances 0.000 description 3
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
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- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000004505 1,2,4-oxadiazol-5-yl group Chemical group O1N=CN=C1* 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N 1,3-Dimethylbenzene Natural products CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- CGXLVFZJJOXEDF-UHFFFAOYSA-N 1,8-naphthyridine-3-carboxylic acid Chemical compound N1=CC=CC2=CC(C(=O)O)=CN=C21 CGXLVFZJJOXEDF-UHFFFAOYSA-N 0.000 description 2
- HXVNBWAKAOHACI-UHFFFAOYSA-N 2,4-dimethyl-3-pentanone Chemical compound CC(C)C(=O)C(C)C HXVNBWAKAOHACI-UHFFFAOYSA-N 0.000 description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
- NDOPHXWIAZIXPR-UHFFFAOYSA-N 2-bromobenzaldehyde Chemical compound BrC1=CC=CC=C1C=O NDOPHXWIAZIXPR-UHFFFAOYSA-N 0.000 description 2
- IBMUHJIDXFMZPI-UHFFFAOYSA-N 2-chlorobenzaldehyde Chemical compound ClC1=CC=CC=C1C=O.ClC1=CC=CC=C1C=O IBMUHJIDXFMZPI-UHFFFAOYSA-N 0.000 description 2
- NTWBHJYRDKBGBR-UHFFFAOYSA-N 2-ethylbenzaldehyde Chemical compound CCC1=CC=CC=C1C=O NTWBHJYRDKBGBR-UHFFFAOYSA-N 0.000 description 2
- XJOLYWNYMOPRKQ-WAYWQWQTSA-N 2-methoxyethyl (z)-3-aminobut-2-enoate Chemical compound COCCOC(=O)\C=C(\C)N XJOLYWNYMOPRKQ-WAYWQWQTSA-N 0.000 description 2
- CMWKITSNTDAEDT-UHFFFAOYSA-N 2-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC=C1C=O CMWKITSNTDAEDT-UHFFFAOYSA-N 0.000 description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 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
- ZRYZBQLXDKPBDU-UHFFFAOYSA-N 4-bromobenzaldehyde Chemical compound BrC1=CC=C(C=O)C=C1 ZRYZBQLXDKPBDU-UHFFFAOYSA-N 0.000 description 2
- BZCOHGUBYSDFET-UHFFFAOYSA-N 4-chloro-3-methoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC=C1Cl BZCOHGUBYSDFET-UHFFFAOYSA-N 0.000 description 2
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 2
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- BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
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- 238000004458 analytical method Methods 0.000 description 2
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 238000010575 fractional recrystallization Methods 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
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- DIWWDNJUKATEGY-WAYWQWQTSA-N propyl (z)-3-aminobut-2-enoate Chemical compound CCCOC(=O)\C=C(\C)N DIWWDNJUKATEGY-WAYWQWQTSA-N 0.000 description 1
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
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- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
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- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Substances SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 1
- 229940098465 tincture Drugs 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
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- 239000008215 water for injection Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms 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
- A61P3/00—Drugs for disorders of the metabolism
-
- 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
- A61P9/08—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
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 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)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyridine Compounds (AREA)
- Storage Of Fruits Or Vegetables (AREA)
- Protection Of Plants (AREA)
- Medicines Containing Plant Substances (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823247118 DE3247118A1 (de) | 1982-12-20 | 1982-12-20 | Neue substituierte 1,4-dihydropyridine, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS961383A2 CS961383A2 (en) | 1985-07-16 |
| CS241144B2 true CS241144B2 (en) | 1986-03-13 |
Family
ID=6181182
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS839613A CS241144B2 (en) | 1982-12-20 | 1983-12-19 | Method of new substituted 1,4-dihydropyridines production |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4558058A (forum.php) |
| EP (1) | EP0116708B1 (forum.php) |
| JP (1) | JPS59118783A (forum.php) |
| KR (1) | KR840006969A (forum.php) |
| AT (1) | ATE19776T1 (forum.php) |
| AU (1) | AU562583B2 (forum.php) |
| CA (1) | CA1194480A (forum.php) |
| CS (1) | CS241144B2 (forum.php) |
| DD (1) | DD215548A5 (forum.php) |
| DE (2) | DE3247118A1 (forum.php) |
| DK (1) | DK562683A (forum.php) |
| ES (1) | ES8406193A1 (forum.php) |
| FI (1) | FI834451A7 (forum.php) |
| GR (1) | GR79484B (forum.php) |
| HU (1) | HU194556B (forum.php) |
| NO (1) | NO834480L (forum.php) |
| PH (1) | PH20327A (forum.php) |
| PL (1) | PL140526B1 (forum.php) |
| SU (1) | SU1360585A3 (forum.php) |
| ZA (1) | ZA839382B (forum.php) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4414213A (en) * | 1982-03-22 | 1983-11-08 | Mead Johnson & Company | Dihydropyridyl cyclic imidate esters and their pharmaceutical use |
| 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 |
| DE3431862A1 (de) * | 1984-08-30 | 1986-03-13 | Bayer Ag, 5090 Leverkusen | Neue 1,4-dihydropyridine, verfahren zu ihrer herstellung sowie ihre verwendung in arzneimitteln |
| US5326772A (en) * | 1984-09-28 | 1994-07-05 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Diaryl compounds for their use |
| JPS6191185A (ja) | 1984-10-11 | 1986-05-09 | Sumitomo Seiyaku Kk | 新規なオキサジアゾリル−１，４−ジヒドロピリジン誘導体 |
| DE3443179A1 (de) * | 1984-11-27 | 1986-05-28 | Cassella Ag, 6000 Frankfurt | 1,4-dihydropyridine, verfahren zu ihrer herstellung und ihre verwendung |
| US4650805A (en) * | 1985-12-02 | 1987-03-17 | Warner-Lambert Company | 4-(1,2,5,6-Tetrahydro-1-alkyl-3-pyridinyl)-2-thiazolamines and 4-(hexahydro-1-alkyl-3-pyridinyl)-2-thiazolamines having anti-psychotic activity |
| US4920225A (en) * | 1986-12-22 | 1990-04-24 | Laboratoires Syntex S.A. | Resolution of 1,4-dihydropyridine derivatives |
| ES2059416T3 (es) * | 1987-03-27 | 1994-11-16 | Byk Gulden Lomberg Chem Fab | 1,4-dihidropiridina-enantiomeros. |
| SE8703881D0 (sv) * | 1987-10-08 | 1987-10-08 | Haessle Ab | New pharmaceutical preparation |
| FR2627696B1 (fr) * | 1988-02-26 | 1991-09-13 | Fournier Innovation Synergie | Nouvelle forme galenique du fenofibrate |
| DE3807895A1 (de) * | 1988-03-10 | 1989-09-21 | Knoll Ag | Erzeugnisse, enthaltend einen calciumantagonisten und einen lipidsenker |
| US5276150A (en) * | 1989-05-31 | 1994-01-04 | Fujirebio Inc. | 1,4-dihydropyridine derivatives |
| FR2758459B1 (fr) * | 1997-01-17 | 1999-05-07 | Pharma Pass | Composition pharmaceutique de fenofibrate presentant une biodisponibilite elevee et son procede de preparation |
| US6531158B1 (en) | 2000-08-09 | 2003-03-11 | Impax Laboratories, Inc. | Drug delivery system for enhanced bioavailability of hydrophobic active ingredients |
| US7312337B2 (en) * | 2004-09-30 | 2007-12-25 | Eastman Kodak Company | Oxadiazoles and their manufacture |
| DE102006044696A1 (de) * | 2006-09-22 | 2008-03-27 | Bayer Healthcare Ag | 3-Cyano-5-thiazaheteroaryl-dihydropyridine und ihre Verwendung |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3647809A (en) * | 1968-04-26 | 1972-03-07 | Chinoin Gyogyszer Es Vegyeszet | Certain pyridyl-1 2 4-oxadiazole derivatives |
| DE1963186C3 (de) * | 1969-12-17 | 1979-02-15 | Bayer Ag, 5090 Leverkusen | Schwefelhaltige 1,4-Dihydropyridin-33-dicarbonsäureester |
| DE2005116C3 (de) * | 1970-02-05 | 1980-02-14 | Bayer Ag, 5090 Leverkusen | Symmetrische 1,4-Dihydropyridin-3,5-dicarbonsäureester |
| CA962269A (en) * | 1971-05-05 | 1975-02-04 | Robert E. Grahame (Jr.) | Thiazoles, and their use as insecticides |
| GB1552911A (en) * | 1975-07-02 | 1979-09-19 | Fujisawa Pharmaceutical Co | 1,4 dihydropyridine derivatives and the preparation thereof |
| DE2747513A1 (de) * | 1977-10-22 | 1979-05-03 | Bayer Ag | Dihydropyridine mit schwefelhaltigen estergruppierungen |
| US4144343A (en) * | 1978-01-04 | 1979-03-13 | Merck & Co., Inc. | Heterocycle substituted (3-loweralkylamino-2-R1 O-propoxy)pyridines |
| DE2847236A1 (de) * | 1978-10-31 | 1980-05-14 | Bayer Ag | Neue dihydropyridine mit substituierten estergruppierungen, mehrer verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| DE3022030A1 (de) * | 1980-06-12 | 1981-12-17 | Bayer Ag, 5090 Leverkusen | 4-thiazol- bzw. 4-imidazol-substituierte, 1,4-dihydropyridine, verfahren zu deren herstellung sowie diese enthaltende arzneimittel |
| US4414213A (en) * | 1982-03-22 | 1983-11-08 | Mead Johnson & Company | Dihydropyridyl cyclic imidate esters and their pharmaceutical use |
-
1982
- 1982-12-20 DE DE19823247118 patent/DE3247118A1/de not_active Withdrawn
-
1983
- 1983-12-05 FI FI834451A patent/FI834451A7/fi not_active Application Discontinuation
- 1983-12-06 DK DK562683A patent/DK562683A/da not_active Application Discontinuation
- 1983-12-06 NO NO834480A patent/NO834480L/no unknown
- 1983-12-09 US US06/560,197 patent/US4558058A/en not_active Expired - Fee Related
- 1983-12-14 EP EP83112562A patent/EP0116708B1/de not_active Expired
- 1983-12-14 DE DE8383112562T patent/DE3363545D1/de not_active Expired
- 1983-12-14 AT AT83112562T patent/ATE19776T1/de active
- 1983-12-19 CA CA000443586A patent/CA1194480A/en not_active Expired
- 1983-12-19 CS CS839613A patent/CS241144B2/cs unknown
- 1983-12-19 ES ES528175A patent/ES8406193A1/es not_active Expired
- 1983-12-19 ZA ZA839382A patent/ZA839382B/xx unknown
- 1983-12-19 SU SU833675005A patent/SU1360585A3/ru active
- 1983-12-19 AU AU22533/83A patent/AU562583B2/en not_active Expired - Fee Related
- 1983-12-19 JP JP58238045A patent/JPS59118783A/ja active Pending
- 1983-12-19 PL PL1983245200A patent/PL140526B1/pl unknown
- 1983-12-19 GR GR73283A patent/GR79484B/el unknown
- 1983-12-19 HU HU834330A patent/HU194556B/hu not_active IP Right Cessation
- 1983-12-19 DD DD83258173A patent/DD215548A5/de unknown
- 1983-12-20 KR KR1019830006046A patent/KR840006969A/ko not_active Ceased
-
1986
- 1986-12-02 PH PH29994A patent/PH20327A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PH20327A (en) | 1986-12-02 |
| CA1194480A (en) | 1985-10-01 |
| DE3247118A1 (de) | 1984-06-20 |
| SU1360585A3 (ru) | 1987-12-15 |
| GR79484B (forum.php) | 1984-10-30 |
| DK562683D0 (da) | 1983-12-06 |
| EP0116708B1 (de) | 1986-05-14 |
| ES528175A0 (es) | 1984-08-01 |
| PL140526B1 (en) | 1987-05-30 |
| CS961383A2 (en) | 1985-07-16 |
| ES8406193A1 (es) | 1984-08-01 |
| FI834451A7 (fi) | 1984-06-21 |
| NO834480L (no) | 1984-06-21 |
| DD215548A5 (de) | 1984-11-14 |
| DE3363545D1 (en) | 1986-06-19 |
| JPS59118783A (ja) | 1984-07-09 |
| US4558058A (en) | 1985-12-10 |
| AU562583B2 (en) | 1987-06-11 |
| DK562683A (da) | 1984-06-21 |
| AU2253383A (en) | 1984-06-28 |
| ZA839382B (en) | 1984-08-29 |
| FI834451A0 (fi) | 1983-12-05 |
| KR840006969A (ko) | 1984-12-04 |
| PL245200A1 (en) | 1985-02-27 |
| HU194556B (en) | 1988-02-29 |
| EP0116708A1 (de) | 1984-08-29 |
| ATE19776T1 (de) | 1986-05-15 |
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