FI60862C - Foerfarande foer framstaellning av terapeutiskt anvaendbara aminoalkylidenamino-1,4-dihydropyridiner - Google Patents
Foerfarande foer framstaellning av terapeutiskt anvaendbara aminoalkylidenamino-1,4-dihydropyridiner Download PDFInfo
- Publication number
- FI60862C FI60862C FI772569A FI772569A FI60862C FI 60862 C FI60862 C FI 60862C FI 772569 A FI772569 A FI 772569A FI 772569 A FI772569 A FI 772569A FI 60862 C FI60862 C FI 60862C
- Authority
- FI
- Finland
- Prior art keywords
- methyl
- dihydropyridine
- mmol
- alkyl
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 230000001225 therapeutic effect Effects 0.000 title description 3
- -1 nitroxy Chemical group 0.000 claims description 31
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000000460 chlorine Substances 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
- YSMRAFSHKXBOFO-UHFFFAOYSA-N 1,4-dihydropyridin-2-amine Chemical compound NC1=CCC=CN1 YSMRAFSHKXBOFO-UHFFFAOYSA-N 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical group 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 239000003086 colorant Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 93
- 150000001875 compounds Chemical class 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- BWKAYBPLDRWMCJ-UHFFFAOYSA-N 1,1-diethoxy-n,n-dimethylmethanamine Chemical compound CCOC(N(C)C)OCC BWKAYBPLDRWMCJ-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- VGUWZCUCNQXGBU-UHFFFAOYSA-N 3-[(4-methylpiperazin-1-yl)methyl]-5-nitro-1h-indole Chemical compound C1CN(C)CCN1CC1=CNC2=CC=C([N+]([O-])=O)C=C12 VGUWZCUCNQXGBU-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- XUFDMPZZAIRCGV-UHFFFAOYSA-N 1,1-diethoxy-n,n-dimethylethanamine Chemical compound CCOC(C)(N(C)C)OCC XUFDMPZZAIRCGV-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
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000002220 antihypertensive agent Substances 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- RQDSQXSFJWNZRN-UHFFFAOYSA-N n-butyl-n-(diethoxymethyl)butan-1-amine Chemical compound CCCCN(CCCC)C(OCC)OCC RQDSQXSFJWNZRN-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 210000002345 respiratory system Anatomy 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 230000002792 vascular Effects 0.000 description 2
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical class C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- SBFJSZPNSCJDKI-UHFFFAOYSA-N 1-(diethoxymethyl)piperidine Chemical compound CCOC(OCC)N1CCCCC1 SBFJSZPNSCJDKI-UHFFFAOYSA-N 0.000 description 1
- OXHNLMTVIGZXSG-UHFFFAOYSA-N 1-Methylpyrrole Chemical compound CN1C=CC=C1 OXHNLMTVIGZXSG-UHFFFAOYSA-N 0.000 description 1
- JQCSUVJDBHJKNG-UHFFFAOYSA-N 1-methoxy-ethyl Chemical group C[CH]OC JQCSUVJDBHJKNG-UHFFFAOYSA-N 0.000 description 1
- OXQGTIUCKGYOAA-UHFFFAOYSA-N 2-Ethylbutanoic acid Chemical compound CCC(CC)C(O)=O OXQGTIUCKGYOAA-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 206010001497 Agitation Diseases 0.000 description 1
- CYCBGAZBTNDDBN-UHFFFAOYSA-N C(C)(C)OC(=O)C=1C(C(=C(NC1C)N=CN1CCCCC1)C(=O)OCC)C1=C(C=CC=C1)Cl Chemical compound C(C)(C)OC(=O)C=1C(C(=C(NC1C)N=CN1CCCCC1)C(=O)OCC)C1=C(C=CC=C1)Cl CYCBGAZBTNDDBN-UHFFFAOYSA-N 0.000 description 1
- WWMOCEUGBRRCKR-UHFFFAOYSA-N C(C)ON1N(CCCC1)OCC Chemical compound C(C)ON1N(CCCC1)OCC WWMOCEUGBRRCKR-UHFFFAOYSA-N 0.000 description 1
- HGWPJWFKOVOYCV-UHFFFAOYSA-N CNC.CNC.CN(C=O)C Chemical compound CNC.CNC.CN(C=O)C HGWPJWFKOVOYCV-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 239000004367 Lipase Substances 0.000 description 1
- 102000004882 Lipase Human genes 0.000 description 1
- 108090001060 Lipase Proteins 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 208000007101 Muscle Cramp Diseases 0.000 description 1
- 206010049816 Muscle tightness Diseases 0.000 description 1
- 208000005392 Spasm Diseases 0.000 description 1
- 210000001015 abdomen Anatomy 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 229940127088 antihypertensive drug Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001722 carbon compounds Chemical class 0.000 description 1
- 229950005499 carbon tetrachloride Drugs 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 230000003293 cardioprotective effect Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- VQZSDRXKLXBRHJ-UHFFFAOYSA-N diethyl 2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1 VQZSDRXKLXBRHJ-UHFFFAOYSA-N 0.000 description 1
- UZYJNISTYPQLBW-UHFFFAOYSA-N diethyl 2-amino-6-methyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C)NC(N)=C(C(=O)OCC)C1C1=CC=CC=C1 UZYJNISTYPQLBW-UHFFFAOYSA-N 0.000 description 1
- DXWGTNFNFUBGGP-UHFFFAOYSA-N diethyl 2-methyl-4-(2-nitrophenyl)-6-(piperidin-1-ylmethylideneamino)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C=1C(C=2C(=CC=CC=2)[N+]([O-])=O)C(C(=O)OCC)=C(C)NC=1N=CN1CCCCC1 DXWGTNFNFUBGGP-UHFFFAOYSA-N 0.000 description 1
- FGCXURDEFHVFTI-UHFFFAOYSA-N diethyl 4-(2-chlorophenyl)-2-methyl-6-(piperidin-1-ylmethylideneamino)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C=1C(C=2C(=CC=CC=2)Cl)C(C(=O)OCC)=C(C)NC=1N=CN1CCCCC1 FGCXURDEFHVFTI-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 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
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002170 ethers Chemical class 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
- KBEBGUQPQBELIU-UHFFFAOYSA-N ethyl 3-phenylprop-2-enoate Chemical compound CCOC(=O)C=CC1=CC=CC=C1 KBEBGUQPQBELIU-UHFFFAOYSA-N 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 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
- 230000001771 impaired effect Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 235000019421 lipase Nutrition 0.000 description 1
- 230000005923 long-lasting effect Effects 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
- 210000002464 muscle smooth vascular Anatomy 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
- 239000000243 solution Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 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
- 239000003826 tablet Substances 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
- 230000003639 vasoconstrictive effect Effects 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2639257 | 1976-09-01 | ||
| DE19762639257 DE2639257A1 (de) | 1976-09-01 | 1976-09-01 | Aminoalkylidenamino-1,4-dihydropyridine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI772569A7 FI772569A7 (fi) | 1978-03-02 |
| FI60862B FI60862B (fi) | 1981-12-31 |
| FI60862C true FI60862C (fi) | 1982-04-13 |
Family
ID=5986848
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI772569A FI60862C (fi) | 1976-09-01 | 1977-08-30 | Foerfarande foer framstaellning av terapeutiskt anvaendbara aminoalkylidenamino-1,4-dihydropyridiner |
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 |
| CH634053A5 (de) | 1983-01-14 |
| AT364359B (de) | 1981-10-12 |
| NL7709508A (nl) | 1978-03-03 |
| SE7709797L (sv) | 1978-03-02 |
| BE858269A (fr) | 1978-02-28 |
| DE2639257A1 (de) | 1978-03-02 |
| ES461994A1 (es) | 1978-12-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: BAYER AKTIENGESELLSCHAFT |