CH634053A5 - Verfahren zur herstellung neuer aminoalkylidenamino-1.4-dihydropyridine. - Google Patents
Verfahren zur herstellung neuer aminoalkylidenamino-1.4-dihydropyridine. Download PDFInfo
- Publication number
- CH634053A5 CH634053A5 CH1057577A CH1057577A CH634053A5 CH 634053 A5 CH634053 A5 CH 634053A5 CH 1057577 A CH1057577 A CH 1057577A CH 1057577 A CH1057577 A CH 1057577A CH 634053 A5 CH634053 A5 CH 634053A5
- Authority
- CH
- Switzerland
- Prior art keywords
- methyl
- dihydropyridine
- amino
- ester
- mmol
- Prior art date
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- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 title description 4
- 238000004519 manufacturing process Methods 0.000 title description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 95
- -1 pyrryl Chemical group 0.000 description 91
- 125000004432 carbon atom Chemical group C* 0.000 description 38
- 235000019441 ethanol Nutrition 0.000 description 34
- 125000000217 alkyl group Chemical group 0.000 description 31
- 125000001424 substituent group Chemical group 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 14
- 125000004093 cyano group Chemical group *C#N 0.000 description 13
- 125000004663 dialkyl amino group Chemical group 0.000 description 13
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 13
- 125000003545 alkoxy group Chemical group 0.000 description 12
- 125000003277 amino group Chemical group 0.000 description 12
- 229910052736 halogen Inorganic materials 0.000 description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 12
- 239000000460 chlorine Substances 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 11
- 150000002367 halogens Chemical class 0.000 description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 description 11
- BWKAYBPLDRWMCJ-UHFFFAOYSA-N 1,1-diethoxy-n,n-dimethylmethanamine Chemical compound CCOC(N(C)C)OCC BWKAYBPLDRWMCJ-UHFFFAOYSA-N 0.000 description 10
- 125000003710 aryl alkyl group Chemical group 0.000 description 10
- 229910052760 oxygen Inorganic materials 0.000 description 10
- 239000001301 oxygen Substances 0.000 description 10
- 229910052717 sulfur Inorganic materials 0.000 description 10
- 150000005840 aryl radicals Chemical class 0.000 description 9
- 125000005842 heteroatom Chemical group 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 125000004434 sulfur atom Chemical group 0.000 description 8
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 125000004430 oxygen atom Chemical group O* 0.000 description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 5
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 5
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- XUFDMPZZAIRCGV-UHFFFAOYSA-N 1,1-diethoxy-n,n-dimethylethanamine Chemical compound CCOC(C)(N(C)C)OCC XUFDMPZZAIRCGV-UHFFFAOYSA-N 0.000 description 4
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 4
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- 125000002947 alkylene group Chemical group 0.000 description 4
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- 125000004494 ethyl ester group Chemical group 0.000 description 4
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- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 4
- 125000004076 pyridyl group Chemical group 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- YSMRAFSHKXBOFO-UHFFFAOYSA-N 1,4-dihydropyridin-2-amine Chemical class NC1=CCC=CN1 YSMRAFSHKXBOFO-UHFFFAOYSA-N 0.000 description 3
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- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 3
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- 125000002541 furyl group Chemical group 0.000 description 3
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- 150000004702 methyl esters Chemical class 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 125000002971 oxazolyl group Chemical group 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 125000003373 pyrazinyl group Chemical group 0.000 description 3
- 125000003226 pyrazolyl group Chemical group 0.000 description 3
- 125000002098 pyridazinyl group Chemical group 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 3
- 125000005493 quinolyl group Chemical group 0.000 description 3
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- 239000000454 talc Substances 0.000 description 3
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- 125000000335 thiazolyl group Chemical group 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 3
- NNZYKBVCKKLXLJ-UHFFFAOYSA-N 3-o-ethyl 5-o-propan-2-yl 2-amino-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(N)NC(C)=C(C(=O)OC(C)C)C1C1=CC=CC([N+]([O-])=O)=C1 NNZYKBVCKKLXLJ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
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- ZMSCKIVKDHICBT-UHFFFAOYSA-N diethyl 2-amino-4-(3-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C)NC(N)=C(C(=O)OCC)C1C1=CC=CC(Cl)=C1 ZMSCKIVKDHICBT-UHFFFAOYSA-N 0.000 description 1
- YVTGPBMVXPDGGY-UHFFFAOYSA-N diethyl 2-amino-4-(3-methoxyphenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C)NC(N)=C(C(=O)OCC)C1C1=CC=CC(OC)=C1 YVTGPBMVXPDGGY-UHFFFAOYSA-N 0.000 description 1
- MJFHOUORUVEQHP-UHFFFAOYSA-N diethyl 2-amino-6-methyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C)NC(N)=C(C(=O)OCC)C1C1=CC=CC=C1[N+]([O-])=O MJFHOUORUVEQHP-UHFFFAOYSA-N 0.000 description 1
- 229940085304 dihydropyridine derivative selective calcium channel blockers with mainly vascular effects Drugs 0.000 description 1
- 125000004925 dihydropyridyl group Chemical class N1(CC=CC=C1)* 0.000 description 1
- WEHQHBXSHNZFBD-UHFFFAOYSA-N dimethyl 2-amino-6-methyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(NC(=C(C1C1=C(C=CC=C1)[N+](=O)[O-])C(=O)OC)C)N WEHQHBXSHNZFBD-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 1
- JHKOMVRNWGLUFA-UHFFFAOYSA-N dipropan-2-yl pyridine-3,5-dicarboxylate Chemical compound CC(C)OC(=O)C1=CN=CC(C(=O)OC(C)C)=C1 JHKOMVRNWGLUFA-UHFFFAOYSA-N 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000839 emulsion Substances 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
- KNJFGQHKBBGFQC-UHFFFAOYSA-N ethyl propanoate piperidine Chemical compound C1CCNCC1.CCOC(=O)CC KNJFGQHKBBGFQC-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 235000019264 food flavour enhancer Nutrition 0.000 description 1
- KNPWRSVXYPZCOS-UHFFFAOYSA-N formic acid;piperidine Chemical compound [O-]C=O.C1CC[NH2+]CC1 KNPWRSVXYPZCOS-UHFFFAOYSA-N 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- UWNADWZGEHDQAB-UHFFFAOYSA-N i-Pr2C2H4i-Pr2 Natural products CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 235000021190 leftovers Nutrition 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000006187 pill 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
- 229920001592 potato starch Polymers 0.000 description 1
- VSRSQDMWBSKNSF-UHFFFAOYSA-N propan-2-yl pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1 VSRSQDMWBSKNSF-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 210000002345 respiratory system Anatomy 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
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Substances [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 230000003235 vasospasmolytic effect Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000005853 β-dimethylaminoethyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
- C07D211/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pulmonology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762639257 DE2639257A1 (de) | 1976-09-01 | 1976-09-01 | Aminoalkylidenamino-1,4-dihydropyridine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH634053A5 true CH634053A5 (de) | 1983-01-14 |
Family
ID=5986848
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1057577A CH634053A5 (de) | 1976-09-01 | 1977-08-30 | Verfahren zur herstellung neuer aminoalkylidenamino-1.4-dihydropyridine. |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4146627A (enExample) |
| JP (1) | JPS6026106B2 (enExample) |
| AT (1) | AT364359B (enExample) |
| BE (1) | BE858269A (enExample) |
| CH (1) | CH634053A5 (enExample) |
| DE (1) | DE2639257A1 (enExample) |
| ES (1) | ES461994A1 (enExample) |
| FI (1) | FI60862C (enExample) |
| FR (1) | FR2363554A1 (enExample) |
| GB (1) | GB1554495A (enExample) |
| NL (1) | NL7709508A (enExample) |
| SE (1) | SE7709797L (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2835069A1 (de) * | 1978-08-10 | 1980-02-21 | Bayer Ag | N-amino-3,4,5-trihydroxypiperidine, ihre herstellung und verwendung |
| NZ193167A (en) | 1979-03-27 | 1984-08-24 | Boots Co Plc | Quinoline derivatives and pharmaceutical compositions |
| 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 |
| US4419518A (en) * | 1982-07-26 | 1983-12-06 | Tokyo Tanabe Co. L.T.D. | 1,4-Dihydropyridine derivatives |
| US4520131A (en) * | 1983-03-03 | 1985-05-28 | Usv Pharmaceutical | Antihypertensive N-substituted 1,4-dihydropyridines |
| GR851819B (enExample) * | 1984-08-17 | 1985-11-26 | Wyeth John & Brother Ltd | |
| US4652573A (en) * | 1985-03-14 | 1987-03-24 | Nelson Research & Development Co. | Calcium antagonist N-hetero ester 1,4-dihydropyridines |
| US4732898A (en) * | 1986-04-29 | 1988-03-22 | Warner-Lambert Company | 2-(2-aryl-2-oxoalkylidene) analogs of-3,5-pyridinedicarboxylic acid dialkyl esters useful for treatment of cardiovascular disorders |
| US5220027A (en) * | 1987-04-14 | 1993-06-15 | Sumitomo Chemical Company, Limited | Sulfone-containing azamethide compounds with a nitrogen-containing aromatic ring of nitrogen containing aliphatic |
| US5028708A (en) * | 1987-04-14 | 1991-07-02 | Sumitomo Chemical Company, Limited | Azamethinyl quinoline derivatives |
| GR1002248B (en) * | 1988-03-08 | 1996-04-23 | Egyt Gyogyszervegyeszeti Gyar | 1,4-dihydropyridine derivatives preparation method |
| DE4313696A1 (de) * | 1993-04-27 | 1994-11-03 | Bayer Ag | 2-Amino-4-heteroaryl-1,4-dihydropyridine, Verfahren zu ihrer Herstellung und ihre Verwendung in Arzneimitteln |
| JP3394215B2 (ja) | 1999-07-29 | 2003-04-07 | 株式会社 日立インダストリイズ | フィルム減圧貼り合わせ装置 |
| CN1280674C (zh) * | 2001-03-29 | 2006-10-18 | 日立化成工业株式会社 | 电路形成用感光性膜及印刷配线板的制造方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3946026A (en) * | 1972-03-06 | 1976-03-23 | Bayer Aktiengesellschaft | 2-Amino-1,4-dihydropyridine derivatives |
| DE2239815C2 (de) * | 1972-08-12 | 1983-02-10 | Bayer Ag, 5090 Leverkusen | 2-Alkylamino-dihydropyridine, Verfahren zu ihrer Herstellung sowie diese enthaltende Arzneimittel |
| GB1552911A (en) * | 1975-07-02 | 1979-09-19 | Fujisawa Pharmaceutical Co | 1,4 dihydropyridine derivatives and the preparation thereof |
-
1976
- 1976-09-01 DE DE19762639257 patent/DE2639257A1/de not_active Withdrawn
-
1977
- 1977-08-26 US US05/828,136 patent/US4146627A/en not_active Expired - Lifetime
- 1977-08-29 NL NL7709508A patent/NL7709508A/xx not_active Application Discontinuation
- 1977-08-30 GB GB36177/77A patent/GB1554495A/en not_active Expired
- 1977-08-30 JP JP52103283A patent/JPS6026106B2/ja not_active Expired
- 1977-08-30 CH CH1057577A patent/CH634053A5/de not_active IP Right Cessation
- 1977-08-30 FI FI772569A patent/FI60862C/fi not_active IP Right Cessation
- 1977-08-31 ES ES461994A patent/ES461994A1/es not_active Expired
- 1977-08-31 SE SE7709797A patent/SE7709797L/xx not_active Application Discontinuation
- 1977-08-31 BE BE180564A patent/BE858269A/xx unknown
- 1977-08-31 FR FR7726474A patent/FR2363554A1/fr active Granted
- 1977-09-01 AT AT0629677A patent/AT364359B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ATA629677A (de) | 1981-03-15 |
| JPS6026106B2 (ja) | 1985-06-21 |
| FI60862B (fi) | 1981-12-31 |
| US4146627A (en) | 1979-03-27 |
| FI772569A7 (fi) | 1978-03-02 |
| FR2363554B1 (enExample) | 1980-08-08 |
| GB1554495A (en) | 1979-10-24 |
| FR2363554A1 (fr) | 1978-03-31 |
| JPS5331670A (en) | 1978-03-25 |
| AT364359B (de) | 1981-10-12 |
| NL7709508A (nl) | 1978-03-03 |
| SE7709797L (sv) | 1978-03-02 |
| BE858269A (fr) | 1978-02-28 |
| FI60862C (fi) | 1982-04-13 |
| DE2639257A1 (de) | 1978-03-02 |
| ES461994A1 (es) | 1978-12-01 |
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