HU188343B - Process for preparing dihydropyridines and intermediary products thereof - Google Patents
Process for preparing dihydropyridines and intermediary products thereof Download PDFInfo
- Publication number
- HU188343B HU188343B HU831793A HU179383A HU188343B HU 188343 B HU188343 B HU 188343B HU 831793 A HU831793 A HU 831793A HU 179383 A HU179383 A HU 179383A HU 188343 B HU188343 B HU 188343B
- Authority
- HU
- Hungary
- Prior art keywords
- methyl
- formula
- dihydropyridine
- preparation
- compounds
- Prior art date
Links
- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 title claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 34
- 238000000034 method Methods 0.000 claims abstract description 20
- 238000002360 preparation method Methods 0.000 claims abstract description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 2
- 239000004480 active ingredient Substances 0.000 claims description 18
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 11
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 10
- -1 aryl mercaptan Chemical compound 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 2
- XBPARUYCBVKSNA-UHFFFAOYSA-N 4-(2,3-dichlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid Chemical compound ClC1=C(C=CC=C1Cl)C1C(=CNC=C1C(=O)O)C(=O)O XBPARUYCBVKSNA-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000012059 conventional drug carrier Substances 0.000 claims 1
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 5
- 125000001424 substituent group Chemical group 0.000 abstract description 3
- 230000001225 therapeutic effect Effects 0.000 abstract description 3
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- MMWRGWQTAMNAFC-UHFFFAOYSA-N 1,2-dihydropyridine Chemical class C1NC=CC=C1 MMWRGWQTAMNAFC-UHFFFAOYSA-N 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 15
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 5
- 229920000159 gelatin Polymers 0.000 description 5
- 235000019322 gelatine Nutrition 0.000 description 5
- 229920001592 potato starch Polymers 0.000 description 5
- 108010010803 Gelatin Proteins 0.000 description 4
- 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 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000008273 gelatin Substances 0.000 description 4
- 235000011852 gelatine desserts Nutrition 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- 239000008101 lactose Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000454 talc Substances 0.000 description 4
- 229910052623 talc Inorganic materials 0.000 description 4
- ZZNQRAVPEGIEJC-UHFFFAOYSA-N 4-(2,3-dichlorophenyl)-2-(dimethoxymethyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylic acid Chemical compound COC(C=1NC(=C(C(C1C(=O)O)C1=C(C(=CC=C1)Cl)Cl)C(=O)O)C)OC ZZNQRAVPEGIEJC-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
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 3
- 229930006000 Sucrose Natural products 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 235000019204 saccharin Nutrition 0.000 description 3
- 239000005720 sucrose Substances 0.000 description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 3
- WCLGKOYRZKHLND-UHFFFAOYSA-N 4-(2,3-dichlorophenyl)-2-(1,3-dithian-2-yl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylic acid Chemical compound S1C(SCCC1)C=1NC(=C(C(C1C(=O)O)C1=C(C(=CC=C1)Cl)Cl)C(=O)O)C WCLGKOYRZKHLND-UHFFFAOYSA-N 0.000 description 2
- ZISYELANAMZJAQ-UHFFFAOYSA-N 4-(2,3-dichlorophenyl)-2-(diethoxymethyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylic acid Chemical compound C(C)OC(C1=C(C(C(=C(N1)C)C(=O)O)C1=C(C(=CC=C1)Cl)Cl)C(=O)O)OCC ZISYELANAMZJAQ-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229930195725 Mannitol Natural products 0.000 description 2
- 206010029897 Obsessive thoughts Diseases 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 230000003276 anti-hypertensive effect Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 229940085304 dihydropyridine derivative selective calcium channel blockers with mainly vascular effects Drugs 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000013355 food flavoring agent Nutrition 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000000594 mannitol Substances 0.000 description 2
- 235000010355 mannitol Nutrition 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical compound CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 2
- 229940081974 saccharin Drugs 0.000 description 2
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 235000010356 sorbitol Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 1
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 1
- ZWJBVEXXAVYZQX-UHFFFAOYSA-N 4-(2,3-dichlorophenyl)-1,2-dimethyl-6-propylsulfanyl-4H-pyridine-3,5-dicarboxylic acid Chemical compound C(CC)SC=1N(C(=C(C(C=1C(=O)O)C1=C(C(=CC=C1)Cl)Cl)C(=O)O)C)C ZWJBVEXXAVYZQX-UHFFFAOYSA-N 0.000 description 1
- SZTOGINUNAULPP-UHFFFAOYSA-N 4-(2,3-dichlorophenyl)-2-formyl-6-methyl-1,4-dihydropyridine-3,5-dicarboxylic acid Chemical compound C(=O)C=1NC(=C(C(C1C(=O)O)C1=C(C(=CC=C1)Cl)Cl)C(=O)O)C SZTOGINUNAULPP-UHFFFAOYSA-N 0.000 description 1
- RZTAMFZIAATZDJ-HNNXBMFYSA-N 5-o-ethyl 3-o-methyl (4s)-4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)[C@@H]1C1=CC=CC(Cl)=C1Cl RZTAMFZIAATZDJ-HNNXBMFYSA-N 0.000 description 1
- 229920000945 Amylopectin Polymers 0.000 description 1
- 241000282817 Bovidae Species 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229920001800 Shellac Polymers 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000001785 acacia senegal l. willd gum Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000004203 carnauba wax Substances 0.000 description 1
- 235000013869 carnauba wax Nutrition 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- YPMPTULBFPFSEQ-PLNGDYQASA-N ethyl (z)-3-aminobut-2-enoate Chemical compound CCOC(=O)\C=C(\C)N YPMPTULBFPFSEQ-PLNGDYQASA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229960003580 felodipine Drugs 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- LGRZIBPPYFCQCX-UHFFFAOYSA-N methyl 2-[(2,3-dichlorophenyl)methylidene]-4,4-dimethoxy-3-oxobutanoate Chemical compound COC(OC)C(=O)C(C(=O)OC)=CC1=CC=CC(Cl)=C1Cl LGRZIBPPYFCQCX-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- HVZWVEKIQMJYIK-UHFFFAOYSA-N nitryl chloride Chemical compound [O-][N+](Cl)=O HVZWVEKIQMJYIK-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003839 salts Chemical group 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000020374 simple syrup Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
- A61P9/12—Antihypertensives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (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)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Superconductors And Manufacturing Methods Therefor (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE8203177 | 1982-05-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU188343B true HU188343B (en) | 1986-04-28 |
Family
ID=20346868
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU831793A HU188343B (en) | 1982-05-21 | 1983-05-20 | Process for preparing dihydropyridines and intermediary products thereof |
| HU852490A HU193785B (en) | 1982-05-21 | 1983-05-20 | Process for producing dihydropyridine derivatives |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU852490A HU193785B (en) | 1982-05-21 | 1983-05-20 | Process for producing dihydropyridine derivatives |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP0095450A3 (enExample) |
| JP (1) | JPS58210064A (enExample) |
| KR (1) | KR900006116B1 (enExample) |
| AU (1) | AU1464483A (enExample) |
| CA (1) | CA1242201A (enExample) |
| DD (2) | DD216454A5 (enExample) |
| DK (1) | DK223783A (enExample) |
| ES (4) | ES522573A0 (enExample) |
| FI (1) | FI79300C (enExample) |
| GB (1) | GB2120251B (enExample) |
| GR (1) | GR78849B (enExample) |
| HU (2) | HU188343B (enExample) |
| IL (1) | IL68604A0 (enExample) |
| IS (1) | IS1380B6 (enExample) |
| MW (1) | MW2083A1 (enExample) |
| NO (1) | NO162515C (enExample) |
| NZ (1) | NZ204284A (enExample) |
| PT (1) | PT76734B (enExample) |
| ZA (1) | ZA833264B (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1204421B (it) * | 1986-06-27 | 1989-03-01 | Boehringer Biochemia Srl | 2-(aminoalchiltio)metil-1,4-diidropiridine,un metodo per la loro preparazione e composizioni farmaceutiche che le contengono |
| HU199796B (en) * | 1985-08-06 | 1990-03-28 | Boehringer Biochemia Srl | Process for producing 2-thiomethyl-substituted-1,4-dihydropyridines and pharmaceutical compositions comprising such compounds |
| IT1197012B (it) * | 1986-07-29 | 1988-11-25 | Boehringer Biochemia Srl | 2-(aciltio) metil diidropiridine, un processo per la loro preparazione e composizioni farmaceutiche che le contengono |
| IT1213555B (it) * | 1986-12-11 | 1989-12-20 | Boehringer Biochemia Srl | 2 metiltiometildiidropiridine, un processo per laloro preparazione e composizioni farmaceutiche che le contengono. |
| IT1213440B (it) * | 1986-12-24 | 1989-12-20 | Boehringer Biochemia Srl | 2-ditioalchil-diidropiridine, un metodo per la loro preparazione e composizioni farmaceutiche chele contengono. |
| IT1204948B (it) * | 1987-03-13 | 1989-03-10 | Boheringer Biochemia Robin S P | 2-tiometil-sostituite-piridine, metodo per la loro preparazione e composizioni farmaceutiche che le contengono. |
| DE3741540A1 (de) * | 1987-12-08 | 1989-06-22 | Bayer Ag | Verfahren zur herstellung von unsymmetrischen dihydropyridinen |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1670827C3 (de) * | 1967-03-20 | 1974-10-24 | Bayer Ag, 5090 Leverkusen | 4-(2'-Nitrophenyl)-2,6-dimethyl-3,5-dicarbmethoxy-1,4-dihydropyridin |
| 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 |
| GB1552911A (en) * | 1975-07-02 | 1979-09-19 | Fujisawa Pharmaceutical Co | 1,4 dihydropyridine derivatives and the preparation thereof |
| DE2740080A1 (de) * | 1977-09-06 | 1979-03-15 | Bayer Ag | 2-alkylenaminodihydropyridine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| SE429652B (sv) * | 1978-06-30 | 1983-09-19 | Haessle Ab | 2.6-dimetyl-4-(2.3-diklorfenyl)-1.4-dihydropyridin-3.5-dikarboxylsyra-3-metylester-5-etylester |
| US4307103A (en) * | 1978-09-08 | 1981-12-22 | Fujisawa Pharmaceutical Co., Ltd. | Dihydropyridine derivative, processes for preparation thereof and pharmaceutical composition comprising the same |
| GB2050375B (en) * | 1979-05-11 | 1983-02-23 | Fujisawa Pharmaceutical Co | 4-cyanophenyl-1,4-dihydropyridine compound processes for preparation thereof and pharmaceutical composition comprising the same |
| SE7910521L (sv) * | 1979-12-20 | 1981-06-21 | Haessle Ab | Nya 2-metyl-6-substituerade-4-(2,3-disubstituerad fenyl)-1,4-dihydropyridin-3,5-diestrar med hypotesiva egenskaper, samt forfarande for deras framstellning, och farmaceutiska beredningar innehallande desamma |
-
1983
- 1983-05-05 IL IL68604A patent/IL68604A0/xx unknown
- 1983-05-06 ZA ZA833264A patent/ZA833264B/xx unknown
- 1983-05-10 CA CA000427859A patent/CA1242201A/en not_active Expired
- 1983-05-13 EP EP83850126A patent/EP0095450A3/en not_active Withdrawn
- 1983-05-18 AU AU14644/83A patent/AU1464483A/en not_active Abandoned
- 1983-05-18 MW MW20/83A patent/MW2083A1/xx unknown
- 1983-05-18 NZ NZ204284A patent/NZ204284A/en unknown
- 1983-05-19 DK DK223783A patent/DK223783A/da not_active Application Discontinuation
- 1983-05-19 FI FI831779A patent/FI79300C/fi not_active IP Right Cessation
- 1983-05-19 GR GR71399A patent/GR78849B/el unknown
- 1983-05-20 DD DD83264593A patent/DD216454A5/de not_active IP Right Cessation
- 1983-05-20 HU HU831793A patent/HU188343B/hu not_active IP Right Cessation
- 1983-05-20 DD DD83251136A patent/DD211554A5/de not_active IP Right Cessation
- 1983-05-20 JP JP58087769A patent/JPS58210064A/ja active Pending
- 1983-05-20 ES ES522573A patent/ES522573A0/es active Granted
- 1983-05-20 PT PT76734A patent/PT76734B/pt not_active IP Right Cessation
- 1983-05-20 HU HU852490A patent/HU193785B/hu unknown
- 1983-05-20 GB GB08314021A patent/GB2120251B/en not_active Expired
- 1983-05-20 IS IS2808A patent/IS1380B6/is unknown
- 1983-05-20 NO NO831807A patent/NO162515C/no unknown
- 1983-05-21 KR KR1019830002236A patent/KR900006116B1/ko not_active Expired
-
1985
- 1985-04-12 ES ES542185A patent/ES8603415A1/es not_active Expired
- 1985-04-12 ES ES542187A patent/ES8603417A1/es not_active Expired
- 1985-04-12 ES ES542186A patent/ES8603416A1/es not_active Expired
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU597784B2 (en) | Dextro-rotatory enantiomer of methyl alpha-5 (4,5,6,7-tetrahydro (3,2-c) thieno pyridyl) (2-chlorophenyl)-acetate, a process for its preparation and the pharmaceutical compositions containing it | |
| EP0264231A1 (en) | Azetidinone derivatives | |
| JPH01294675A (ja) | １，４−ジヒドロピリジン誘導体、これらの製造法およびこれらの薬剤としての適用 | |
| JPH0523269B2 (enExample) | ||
| HU178449B (en) | Process for preparing 1,4-dihydro-pyridine derivatives containing fluorine | |
| HU188343B (en) | Process for preparing dihydropyridines and intermediary products thereof | |
| JPS6025423B2 (ja) | １，４−ジヒドロピリジンの製法 | |
| JPH02180A (ja) | ２，２‐ジメチルクロメン誘導体、その製造方法及びこれを含む薬剤組成物 | |
| PT91783B (pt) | Processo para a preparacao de {(diarilmetoxi) alquil}-1-pirrolidinas e piperidinas | |
| HUT74185A (en) | Process for producig of 5-acyl-1,4-dihydropyridines, their use for producing pharmaceutical compositions and novel 5-acyl-1,4-dihydropyridines | |
| US4049816A (en) | Antiviral 2-amino-5-[1-(indol-3-yl)alkyl]-2-thiazolin-4-ones | |
| FR2460934A1 (fr) | Derives d'isoquinoleine contenant du soufre, procedes pour leur preparation et compositions pharmaceutiques les contenant | |
| KR900006682B1 (ko) | 디히드로피리딘과 그 반응 중간체의 제조 방법 | |
| HU179951B (en) | Process for preparing 1,2,4-oxadiazolin-5-one derivatives and pharmaceutical compositions containing thereof | |
| US4002753A (en) | 6-Substituted 3-carbethoxyhydrazinopyridazines | |
| US3962262A (en) | 1,8-naphthyridine compounds | |
| EP0007648B1 (en) | New acylureas with pharmaceutical activity, the process for their preparation, and pharmaceutical compositions which contain them | |
| WO2008069469A1 (en) | Crystalline s-(-)-amlodipine camsylate anhydride and preparation method thereof | |
| US4031103A (en) | 1,8-Naphthyridine compounds | |
| EP0119541A1 (en) | Substituted 4,10-dihydro-10-oxothieno-benzoxepins, a process for their preparation and their use as medicaments | |
| JP2535533B2 (ja) | ベンゾジオキソ−ル誘導体 | |
| JPS6245870B2 (enExample) | ||
| US4542138A (en) | Dioxobenzocyclo-hepta-pyridine compounds, process and use as antihypertensives | |
| FR2515652A1 (fr) | Nouveaux derives de la 1,4-dihydropyridazine, leur preparation et medicaments contenant ces derives | |
| US4841054A (en) | 2,6-dimethyl-3,5-dimethoxycarbonyl-4-(5'-trimethylsilyl-2'-furyl)-1,4-dihydropyridine |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |