FR2490092A1 - Nouvelles compositions pharmaceutiques a base d'un derive de la 1,4-dihydropyridine - Google Patents
Nouvelles compositions pharmaceutiques a base d'un derive de la 1,4-dihydropyridine Download PDFInfo
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- FR2490092A1 FR2490092A1 FR8117448A FR8117448A FR2490092A1 FR 2490092 A1 FR2490092 A1 FR 2490092A1 FR 8117448 A FR8117448 A FR 8117448A FR 8117448 A FR8117448 A FR 8117448A FR 2490092 A1 FR2490092 A1 FR 2490092A1
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- carbon atoms
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- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 21
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical class C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 title description 2
- -1 4-BENZOTHIADIAZOLYL-1,4-DIHYDROPYRIDINE Chemical compound 0.000 claims abstract description 23
- 239000004480 active ingredient Substances 0.000 claims abstract description 20
- 229940124549 vasodilator Drugs 0.000 claims abstract description 4
- 239000003071 vasodilator agent Substances 0.000 claims abstract description 4
- 239000003087 receptor blocking agent Substances 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 146
- 125000000217 alkyl group Chemical group 0.000 claims description 73
- 239000000203 mixture Substances 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 20
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 239000012458 free base Substances 0.000 claims description 10
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- JZQKKSLKJUAGIC-UHFFFAOYSA-N pindolol Chemical compound CC(C)NCC(O)COC1=CC=CC2=C1C=CN2 JZQKKSLKJUAGIC-UHFFFAOYSA-N 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 229910052717 sulfur Chemical group 0.000 claims description 9
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 8
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 239000001301 oxygen Chemical group 0.000 claims description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 7
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 239000011593 sulfur Chemical group 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 239000002981 blocking agent Substances 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 229910002651 NO3 Inorganic materials 0.000 claims description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 101100134927 Gallus gallus COR8 gene Proteins 0.000 claims description 2
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 2
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- WQOWSHMABGCDSG-UHFFFAOYSA-N 4-(2,6-dimethyl-1,4-dihydropyridin-4-yl)-2,1,3-benzoxadiazole Chemical compound N=1ON=C2C=1C=CC=C2C1C=C(NC(=C1)C)C WQOWSHMABGCDSG-UHFFFAOYSA-N 0.000 claims 1
- 241000294754 Macroptilium atropurpureum Species 0.000 claims 1
- 101000927076 Xenopus laevis Apoptosis regulator R11 Proteins 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 238000004806 packaging method and process Methods 0.000 claims 1
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 12
- 229940126208 compound 22 Drugs 0.000 description 12
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 229960002508 pindolol Drugs 0.000 description 8
- 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 6
- 239000008101 lactose Substances 0.000 description 6
- 235000019359 magnesium stearate Nutrition 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000005303 weighing Methods 0.000 description 6
- 206010020772 Hypertension Diseases 0.000 description 5
- 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 4
- 229930195725 Mannitol Natural products 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 239000000594 mannitol Substances 0.000 description 4
- 229960001855 mannitol Drugs 0.000 description 4
- 235000010355 mannitol Nutrition 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 150000005840 aryl radicals Chemical class 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 108020003175 receptors Proteins 0.000 description 3
- 102000005962 receptors Human genes 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000002213 calciumantagonistic effect Effects 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 210000002837 heart atrium Anatomy 0.000 description 2
- 230000001631 hypertensive effect Effects 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 229920006316 polyvinylpyrrolidine Polymers 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 230000036316 preload Effects 0.000 description 2
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- CEMAWMOMDPGJMB-UHFFFAOYSA-N (+-)-Oxprenolol Chemical compound CC(C)NCC(O)COC1=CC=CC=C1OCC=C CEMAWMOMDPGJMB-UHFFFAOYSA-N 0.000 description 1
- NXQMNKUGGYNLBY-GFCCVEGCSA-N (2r)-1-(3-methylphenoxy)-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NC[C@@H](O)COC1=CC=CC(C)=C1 NXQMNKUGGYNLBY-GFCCVEGCSA-N 0.000 description 1
- VIJSPAIQWVPKQZ-BLECARSGSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-4-methylpentanoyl]amino]-4,4-dimethylpentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(C)=O VIJSPAIQWVPKQZ-BLECARSGSA-N 0.000 description 1
- OMBVEVHRIQULKW-DNQXCXABSA-M (3r,5r)-7-[3-(4-fluorophenyl)-8-oxo-7-phenyl-1-propan-2-yl-5,6-dihydro-4h-pyrrolo[2,3-c]azepin-2-yl]-3,5-dihydroxyheptanoate Chemical compound O=C1C=2N(C(C)C)C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C(C=3C=CC(F)=CC=3)C=2CCCN1C1=CC=CC=C1 OMBVEVHRIQULKW-DNQXCXABSA-M 0.000 description 1
- METKIMKYRPQLGS-GFCCVEGCSA-N (R)-atenolol Chemical compound CC(C)NC[C@@H](O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-GFCCVEGCSA-N 0.000 description 1
- TWBNMYSKRDRHAT-RCWTXCDDSA-N (S)-timolol hemihydrate Chemical compound O.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1 TWBNMYSKRDRHAT-RCWTXCDDSA-N 0.000 description 1
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical group C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 1
- SLLFVLKNXABYGI-UHFFFAOYSA-N 1,2,3-benzoxadiazole Chemical group C1=CC=C2ON=NC2=C1 SLLFVLKNXABYGI-UHFFFAOYSA-N 0.000 description 1
- RTAGQMIEWAAKMO-UHFFFAOYSA-N 1-(2-cyclopropylphenoxy)-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(O)COC1=CC=CC=C1C1CC1 RTAGQMIEWAAKMO-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical compound C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- SGUAFYQXFOLMHL-UHFFFAOYSA-N 2-hydroxy-5-{1-hydroxy-2-[(4-phenylbutan-2-yl)amino]ethyl}benzamide Chemical compound C=1C=C(O)C(C(N)=O)=CC=1C(O)CNC(C)CCC1=CC=CC=C1 SGUAFYQXFOLMHL-UHFFFAOYSA-N 0.000 description 1
- SKQDKFOTIPJUSV-UHFFFAOYSA-N 4-[2-[[2-hydroxy-3-(2-methylphenoxy)propyl]amino]ethoxy]benzamide Chemical compound CC1=CC=CC=C1OCC(O)CNCCOC1=CC=C(C(N)=O)C=C1 SKQDKFOTIPJUSV-UHFFFAOYSA-N 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 206010049872 Breast discomfort Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
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- 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 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
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- TZRXHJWUDPFEEY-UHFFFAOYSA-N Pentaerythritol Tetranitrate Chemical compound [O-][N+](=O)OCC(CO[N+]([O-])=O)(CO[N+]([O-])=O)CO[N+]([O-])=O TZRXHJWUDPFEEY-UHFFFAOYSA-N 0.000 description 1
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- DGMJZELBSFOPHH-KVTDHHQDSA-N mannite hexanitrate Chemical compound [O-][N+](=O)OC[C@@H](O[N+]([O-])=O)[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)CO[N+]([O-])=O DGMJZELBSFOPHH-KVTDHHQDSA-N 0.000 description 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 229960002704 metipranolol Drugs 0.000 description 1
- BLWNYSZZZWQCKO-UHFFFAOYSA-N metipranolol hydrochloride Chemical compound [Cl-].CC(C)[NH2+]CC(O)COC1=CC(C)=C(OC(C)=O)C(C)=C1C BLWNYSZZZWQCKO-UHFFFAOYSA-N 0.000 description 1
- IUBSYMUCCVWXPE-UHFFFAOYSA-N metoprolol Chemical compound COCCC1=CC=C(OCC(O)CNC(C)C)C=C1 IUBSYMUCCVWXPE-UHFFFAOYSA-N 0.000 description 1
- 229960002237 metoprolol Drugs 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- UPZVYDSBLFNMLK-UHFFFAOYSA-N nadoxolol Chemical compound C1=CC=C2C(OCC(O)CC(/N)=N/O)=CC=CC2=C1 UPZVYDSBLFNMLK-UHFFFAOYSA-N 0.000 description 1
- 229960004501 nadoxolol Drugs 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 229960004570 oxprenolol Drugs 0.000 description 1
- UFNAECVCKNHAKN-UHFFFAOYSA-N pargolol Chemical compound CC(C)(C)NCC(O)COC1=CC=CC=C1OCC#C UFNAECVCKNHAKN-UHFFFAOYSA-N 0.000 description 1
- 229950003582 pargolol Drugs 0.000 description 1
- 229960004321 pentaerithrityl tetranitrate Drugs 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 230000009090 positive inotropic effect Effects 0.000 description 1
- 229950003591 procinolol Drugs 0.000 description 1
- 229960003712 propranolol Drugs 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 101150035983 str1 gene Proteins 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- MXFWWQICDIZSOA-UHFFFAOYSA-N talinolol Chemical compound C1=CC(OCC(O)CNC(C)(C)C)=CC=C1NC(=O)NC1CCCCC1 MXFWWQICDIZSOA-UHFFFAOYSA-N 0.000 description 1
- 229960003658 talinolol Drugs 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
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229960004605 timolol Drugs 0.000 description 1
- CSUNLSYSEQIDMO-UHFFFAOYSA-N tiprenolol Chemical compound CSC1=CC=CC=C1OCC(O)CNC(C)C CSUNLSYSEQIDMO-UHFFFAOYSA-N 0.000 description 1
- 229950004988 tiprenolol Drugs 0.000 description 1
- 229950003004 tolamolol Drugs 0.000 description 1
- 229950000245 toliprolol Drugs 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- 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
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8030226 | 1980-09-18 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2490092A1 true FR2490092A1 (fr) | 1982-03-19 |
| FR2490092B1 FR2490092B1 (enEXAMPLES) | 1984-11-09 |
Family
ID=10516152
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8117448A Granted FR2490092A1 (fr) | 1980-09-18 | 1981-09-14 | Nouvelles compositions pharmaceutiques a base d'un derive de la 1,4-dihydropyridine |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4510150A (enEXAMPLES) |
| JP (1) | JPS5782315A (enEXAMPLES) |
| AT (1) | AT381023B (enEXAMPLES) |
| AU (1) | AU558670B2 (enEXAMPLES) |
| BE (1) | BE890311A (enEXAMPLES) |
| CA (1) | CA1177754A (enEXAMPLES) |
| CH (1) | CH655658B (enEXAMPLES) |
| DE (1) | DE3136031A1 (enEXAMPLES) |
| FR (1) | FR2490092A1 (enEXAMPLES) |
| GR (1) | GR75349B (enEXAMPLES) |
| HU (1) | HU190355B (enEXAMPLES) |
| IE (1) | IE51791B1 (enEXAMPLES) |
| IL (1) | IL63854A (enEXAMPLES) |
| IT (1) | IT1171533B (enEXAMPLES) |
| NL (1) | NL8104246A (enEXAMPLES) |
| NZ (1) | NZ198368A (enEXAMPLES) |
| PH (1) | PH19782A (enEXAMPLES) |
| PT (1) | PT73679B (enEXAMPLES) |
| SE (1) | SE461014B (enEXAMPLES) |
| ZA (1) | ZA816515B (enEXAMPLES) |
Families Citing this family (7)
| 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 |
| JPS5978186A (ja) * | 1982-10-27 | 1984-05-04 | 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 |
| DE3419131A1 (de) * | 1984-05-23 | 1985-11-28 | Bayer Ag, 5090 Leverkusen | Dihydropyridinkombinationspraeparate und verfahren zu ihrer herstellung |
| SE455836B (sv) * | 1985-10-11 | 1988-08-15 | Haessle Ab | Beredning med kontrollerad frisettning innehallande ett salt av metoprolol samt metod for framstellning av denna beredning |
| SE450087B (sv) * | 1985-10-11 | 1987-06-09 | Haessle Ab | Korn med kontrollerad frisettning av farmaceutiskt aktiva emnen som anbringats teckande pa ett kompakt olosligt kernmaterial |
| DE3610037A1 (de) * | 1986-03-21 | 1987-09-24 | Schering Ag | Nifedipinkombinationspraeparat |
| SE8703881D0 (sv) * | 1987-10-08 | 1987-10-08 | Haessle Ab | New pharmaceutical preparation |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0000150A1 (en) * | 1977-06-20 | 1979-01-10 | Sandoz Ag | Dihydropyridine derivatives, process for their production and pharmaceutical compositions containing them. |
| FR2444681A1 (fr) * | 1978-12-18 | 1980-07-18 | Sandoz Sa | Nouvelles 1,4-dihydropyridines, leur preparation et leur application comme medicaments |
| FR2444680A1 (fr) * | 1978-12-18 | 1980-07-18 | Sandoz Sa | Nouvelles 1,4-dihydropyridines, leur preparation et leur application comme medicaments |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3832470A (en) * | 1968-01-29 | 1974-08-27 | H Russek | Treatment of angina pectoris with a long-acting vasodilating agent and a beta adrenergic receptor blocking agent |
| ZA742728B (en) * | 1973-05-08 | 1975-04-30 | Simes | Pharmaceutical composition for the treatment of coronaric ailments |
| GB1513742A (en) * | 1975-01-31 | 1978-06-07 | Ici Ltd | 6-aryl-2,3,6,7-tetrahydro-5h-pyrrolo(1,2-a)imidazole derivatives processes for their manufacture and compositions containing them |
| GB1527543A (en) * | 1976-04-15 | 1978-10-04 | Degussa | Basically substituted xanthine derivatives |
| DE2949464A1 (de) * | 1978-12-18 | 1980-06-26 | Sandoz Ag | Benzoxadiazole und benzothiadiazole, ihre herstellung und verwendung |
-
1981
- 1981-09-09 CH CH582481A patent/CH655658B/de unknown
- 1981-09-11 DE DE19813136031 patent/DE3136031A1/de active Granted
- 1981-09-11 BE BE1/10314A patent/BE890311A/fr not_active IP Right Cessation
- 1981-09-14 FR FR8117448A patent/FR2490092A1/fr active Granted
- 1981-09-15 NL NL8104246A patent/NL8104246A/nl not_active Application Discontinuation
- 1981-09-16 SE SE8105497A patent/SE461014B/sv not_active IP Right Cessation
- 1981-09-16 GR GR66066A patent/GR75349B/el unknown
- 1981-09-16 IL IL63854A patent/IL63854A/xx not_active IP Right Cessation
- 1981-09-16 CA CA000385994A patent/CA1177754A/en not_active Expired
- 1981-09-16 IT IT49305/81A patent/IT1171533B/it active
- 1981-09-16 NZ NZ198368A patent/NZ198368A/en unknown
- 1981-09-16 PT PT73679A patent/PT73679B/pt not_active IP Right Cessation
- 1981-09-17 AT AT0401181A patent/AT381023B/de not_active IP Right Cessation
- 1981-09-17 JP JP56145659A patent/JPS5782315A/ja active Granted
- 1981-09-17 IE IE2157/81A patent/IE51791B1/en not_active IP Right Cessation
- 1981-09-17 AU AU75443/81A patent/AU558670B2/en not_active Ceased
- 1981-09-17 HU HU812689A patent/HU190355B/hu unknown
- 1981-09-18 PH PH26226A patent/PH19782A/en unknown
- 1981-09-18 ZA ZA816515A patent/ZA816515B/xx unknown
-
1983
- 1983-08-01 US US06/519,002 patent/US4510150A/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0000150A1 (en) * | 1977-06-20 | 1979-01-10 | Sandoz Ag | Dihydropyridine derivatives, process for their production and pharmaceutical compositions containing them. |
| FR2444681A1 (fr) * | 1978-12-18 | 1980-07-18 | Sandoz Sa | Nouvelles 1,4-dihydropyridines, leur preparation et leur application comme medicaments |
| FR2444680A1 (fr) * | 1978-12-18 | 1980-07-18 | Sandoz Sa | Nouvelles 1,4-dihydropyridines, leur preparation et leur application comme medicaments |
Also Published As
| Publication number | Publication date |
|---|---|
| SE8105497L (sv) | 1982-03-19 |
| ATA401181A (de) | 1986-01-15 |
| SE461014B (sv) | 1989-12-18 |
| NZ198368A (en) | 1985-08-30 |
| IT8149305A0 (it) | 1981-09-16 |
| AU7544381A (en) | 1982-04-01 |
| AT381023B (de) | 1986-08-11 |
| NL8104246A (nl) | 1982-04-16 |
| JPH0160009B2 (enEXAMPLES) | 1989-12-20 |
| IE51791B1 (en) | 1987-04-01 |
| AU558670B2 (en) | 1987-02-05 |
| CH655658B (enEXAMPLES) | 1986-05-15 |
| IT1171533B (it) | 1987-06-10 |
| PT73679B (en) | 1983-05-11 |
| DE3136031C2 (enEXAMPLES) | 1993-02-11 |
| CA1177754A (en) | 1984-11-13 |
| FR2490092B1 (enEXAMPLES) | 1984-11-09 |
| PH19782A (en) | 1986-07-02 |
| GR75349B (enEXAMPLES) | 1984-07-13 |
| HU190355B (en) | 1986-08-28 |
| US4510150A (en) | 1985-04-09 |
| DE3136031A1 (de) | 1982-04-08 |
| IL63854A0 (en) | 1981-12-31 |
| BE890311A (fr) | 1982-03-11 |
| PT73679A (en) | 1981-10-01 |
| IL63854A (en) | 1985-08-30 |
| ZA816515B (en) | 1983-04-27 |
| IE812157L (en) | 1982-03-18 |
| JPS5782315A (en) | 1982-05-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| TP | Transmission of property | ||
| ST | Notification of lapse |