DE2210687C3 - 2,6-Diamino-3,5-diäthoxycarbonyldihydropyridine, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel - Google Patents
2,6-Diamino-3,5-diäthoxycarbonyldihydropyridine, Verfahren zu ihrer Herstellung und sie enthaltende ArzneimittelInfo
- Publication number
- DE2210687C3 DE2210687C3 DE2210687A DE2210687A DE2210687C3 DE 2210687 C3 DE2210687 C3 DE 2210687C3 DE 2210687 A DE2210687 A DE 2210687A DE 2210687 A DE2210687 A DE 2210687A DE 2210687 C3 DE2210687 C3 DE 2210687C3
- Authority
- DE
- Germany
- Prior art keywords
- diamino
- ooc
- cooc
- ethanol
- preparation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 14
- 230000008569 process Effects 0.000 title claims description 8
- HQNQRCGPIMGJOM-UHFFFAOYSA-N CCOC(C1=CC(C(OCC)=O)=C(N)NC1N)=O Chemical class CCOC(C1=CC(C(OCC)=O)=C(N)NC1N)=O HQNQRCGPIMGJOM-UHFFFAOYSA-N 0.000 title claims 2
- 239000003814 drug Substances 0.000 title description 5
- 150000001409 amidines Chemical class 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 7
- -1 tritiuomethyl Chemical group 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 38
- 235000019441 ethanol Nutrition 0.000 description 15
- 239000000243 solution Substances 0.000 description 10
- 230000000694 effects Effects 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- HSDKTLKBDJXJQU-UHFFFAOYSA-N ethyl 3-amino-3-iminopropanoate Chemical compound CCOC(=O)CC(N)=N HSDKTLKBDJXJQU-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 206010020772 Hypertension Diseases 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 230000003276 anti-hypertensive effect Effects 0.000 description 3
- 230000036772 blood pressure Effects 0.000 description 3
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- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
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- 229910052623 talc Inorganic materials 0.000 description 3
- PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 description 2
- QHJJSLUZWHFHTK-UHFFFAOYSA-N 3-amino-3-azaniumylidenepropanoate Chemical compound NC(=N)CC(O)=O QHJJSLUZWHFHTK-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229940030600 antihypertensive agent Drugs 0.000 description 2
- 239000002220 antihypertensive agent Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 210000004351 coronary vessel Anatomy 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- BTFQKIATRPGRBS-UHFFFAOYSA-N o-tolualdehyde Chemical compound CC1=CC=CC=C1C=O BTFQKIATRPGRBS-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 210000002460 smooth muscle Anatomy 0.000 description 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 230000002792 vascular Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- KBFLENAAHFHQFJ-UHFFFAOYSA-N 1,4-dihydropyrimidin-6-amine Chemical class NC1=CCNC=N1 KBFLENAAHFHQFJ-UHFFFAOYSA-N 0.000 description 1
- ZDVRPKUWYQVVDX-UHFFFAOYSA-N 2-(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC=CC=C1C=O ZDVRPKUWYQVVDX-UHFFFAOYSA-N 0.000 description 1
- 239000001431 2-methylbenzaldehyde Substances 0.000 description 1
- CMWKITSNTDAEDT-UHFFFAOYSA-N 2-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC=C1C=O CMWKITSNTDAEDT-UHFFFAOYSA-N 0.000 description 1
- NMTUHPSKJJYGML-UHFFFAOYSA-N 3-(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC=CC(C=O)=C1 NMTUHPSKJJYGML-UHFFFAOYSA-N 0.000 description 1
- ZETIVVHRRQLWFW-UHFFFAOYSA-N 3-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC(C=O)=C1 ZETIVVHRRQLWFW-UHFFFAOYSA-N 0.000 description 1
- 206010001497 Agitation Diseases 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- 206010052804 Drug tolerance Diseases 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 244000000231 Sesamum indicum Species 0.000 description 1
- 235000003434 Sesamum indicum Nutrition 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000003440 anti-fibrillation Effects 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
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- 239000001506 calcium phosphate Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- FEWYOZZPZXQCFP-UHFFFAOYSA-N diethyl 1,2-dihydropyridine-3,5-dicarboxylate Chemical compound C(=O)(OCC)C=1C=C(CNC=1)C(=O)OCC FEWYOZZPZXQCFP-UHFFFAOYSA-N 0.000 description 1
- VQKLRVZQQYVIJW-UHFFFAOYSA-N dihydralazine Chemical compound C1=CC=C2C(NN)=NN=C(NN)C2=C1 VQKLRVZQQYVIJW-UHFFFAOYSA-N 0.000 description 1
- 229960002877 dihydralazine Drugs 0.000 description 1
- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 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
- 230000026781 habituation Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 230000004060 metabolic process Effects 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
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 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
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium 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
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 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
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
-
- 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
- A61K31/4418—Non condensed pyridines; Hydrogenated derivatives thereof having a carbocyclic group directly attached to the heterocyclic ring, e.g. cyproheptadine
-
- 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
- A61K31/455—Nicotinic acids, e.g. niacin; Derivatives thereof, e.g. esters, amides
-
- 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
- A61P11/08—Bronchodilators
-
- 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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Epidemiology (AREA)
- Vascular Medicine (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Diabetes (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Priority Applications (41)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2210687A DE2210687C3 (de) | 1972-03-06 | 1972-03-06 | 2,6-Diamino-3,5-diäthoxycarbonyldihydropyridine, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel |
RO73832A RO61192A (enrdf_load_stackoverflow) | 1972-03-06 | 1973-02-13 | |
RO7300082647A RO63068A (enrdf_load_stackoverflow) | 1972-03-06 | 1973-02-13 | |
DD169048A DD106833A5 (enrdf_load_stackoverflow) | 1972-03-06 | 1973-02-26 | |
BG024472A BG20583A3 (bg) | 1972-03-06 | 1973-02-28 | Метод за получаване на 2,6-диамино-дихидропиридини |
BG022858A BG22815A3 (bg) | 1972-03-06 | 1973-02-28 | Метод за получаване на 2,6-диамино-дихидропиридини |
US00336483A US3855231A (en) | 1972-03-06 | 1973-02-28 | 2,6-diamino-1,4-dihydropyridine derivatives |
IL7341664A IL41664A (en) | 1972-03-06 | 1973-03-02 | 2,6-Diamino-dihydropyridines and their pharmaceutical preparations |
CH220176A CH577473A5 (enrdf_load_stackoverflow) | 1972-03-06 | 1973-03-02 | |
CH313273A CH580589A5 (enrdf_load_stackoverflow) | 1972-03-06 | 1973-03-02 | |
LU67147A LU67147A1 (enrdf_load_stackoverflow) | 1972-03-06 | 1973-03-02 | |
FI657/73A FI55996C (fi) | 1972-03-06 | 1973-03-02 | Foerfarande foer framstaellning av 2,6-diamino-dihydropyridiner |
JP2445273A JPS5626659B2 (enrdf_load_stackoverflow) | 1972-03-06 | 1973-03-02 | |
PL1973182270A PL92078B1 (enrdf_load_stackoverflow) | 1972-03-06 | 1973-03-03 | |
PL1973161010A PL89256B1 (enrdf_load_stackoverflow) | 1972-03-06 | 1973-03-03 | |
CA165,209A CA988524A (en) | 1972-03-06 | 1973-03-05 | Process for the preparation of 2,6-diamino-1,4-dihydropyridine derivatives |
IE346/73A IE37370B1 (en) | 1972-03-06 | 1973-03-05 | New 2,6-diamino-dihydropyridines their production and their medicinal use |
DK118073A DK136061C (da) | 1972-03-06 | 1973-03-05 | Fremgangsmade til fremstilling af 2,6-diamino-dihydropyridiner |
SE7303021A SE384208B (sv) | 1972-03-06 | 1973-03-05 | Sett att framstella nya 2,6-diamino-dihydropyridiner |
ZA731501A ZA731501B (en) | 1972-03-06 | 1973-03-05 | New 2,6-diamino-dihydropyridines,their production,and their medicinal use |
BE128374A BE796279A (fr) | 1972-03-06 | 1973-03-05 | Procede de preparation de nouvelles 2,6-diamino-dihydropyridines |
ES412323A ES412323A1 (es) | 1972-03-06 | 1973-03-05 | Procedimiento para la obtencion de 2,6-diaminodihidropiri- dinas. |
KR7300356A KR780000119B1 (en) | 1972-03-06 | 1973-03-05 | New 2.6-diamino-dihydropyridines, their production, and their medicinal use |
HUBA2892A HU167089B (enrdf_load_stackoverflow) | 1972-03-06 | 1973-03-06 | |
AT925774*7A AT327904B (de) | 1972-03-06 | 1973-03-06 | Verfahren zur herstellung von neuen 2,6-diamino-dihydropyridinen |
AT925774A ATA925774A (de) | 1972-03-06 | 1973-03-06 | Verfahren zur herstellung von neuen 2,6-diamino-dihydropyridinen |
FR7307923A FR2181789B1 (enrdf_load_stackoverflow) | 1972-03-06 | 1973-03-06 | |
CS7500003602A CS182792B2 (en) | 1972-03-06 | 1973-03-06 | Method of production of 2,6-diaminodihydropyridines |
GB1075973A GB1379005A (en) | 1972-03-06 | 1973-03-06 | 2,6-diaminodihydropyridines their production and their medicinal use |
CS7300001593A CS182781B2 (en) | 1972-03-06 | 1973-03-06 | Method of producing 2,6-diaminodihydropyridines |
AT197373A AT324338B (de) | 1972-03-06 | 1973-03-06 | Verfahren zur herstellung von neuen 2,6-diamino-dihydropyridinen |
NL7303137A NL7303137A (enrdf_load_stackoverflow) | 1972-03-06 | 1973-03-06 | |
US05/454,996 US3950336A (en) | 1972-03-06 | 1974-03-27 | 2,6-diamino-1,4-dihydropyridine derivatives |
US05/455,258 US3957998A (en) | 1972-03-06 | 1974-03-27 | Use of 2,6-diamino-4-substituted-1,4-dihydropyridine-3,5-dicarboxylic acid esters for effecting coronary vessel dilation and treating hypertension |
US454997A US3887558A (en) | 1972-03-06 | 1974-03-27 | Process for producing 2,6-diamino -1,4- dihydro-3,5-pyridine-dicarboxylates and derivatives thereof |
US455257A US3860601A (en) | 1972-03-06 | 1974-03-27 | 2,6-diamino-1,4-dihydropyridine derivatives |
US05/523,357 US3959474A (en) | 1972-03-06 | 1974-11-13 | 2,6-Diamino-1,4-dihydropyridine-3,5-dicarboxylic acid esters used as coronary vessel dilators and anti-hypertensive agents |
US05/544,837 US4049662A (en) | 1972-03-06 | 1975-01-28 | 4-Quinoline and isoquinoline substituted 2,6-diamino-1,4-dihydropyridine derivatives |
US05/554,135 US4016277A (en) | 1972-03-06 | 1975-02-28 | 4-Quinoline and 4-isoquinoline derivatives of 2,6-diamino-1,4-dihydropyridine |
DK365775A DK365775A (enrdf_load_stackoverflow) | 1972-03-06 | 1975-08-12 | |
JP55185147A JPS5911584B2 (ja) | 1972-03-06 | 1980-12-27 | 2,6−ジアミノ−ジヒドロピリジン類の製造法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2210687A DE2210687C3 (de) | 1972-03-06 | 1972-03-06 | 2,6-Diamino-3,5-diäthoxycarbonyldihydropyridine, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel |
Publications (3)
Publication Number | Publication Date |
---|---|
DE2210687A1 DE2210687A1 (de) | 1973-09-20 |
DE2210687B2 DE2210687B2 (de) | 1980-09-04 |
DE2210687C3 true DE2210687C3 (de) | 1981-09-24 |
Family
ID=5838037
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE2210687A Expired DE2210687C3 (de) | 1972-03-06 | 1972-03-06 | 2,6-Diamino-3,5-diäthoxycarbonyldihydropyridine, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel |
Country Status (24)
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2210687C3 (de) * | 1972-03-06 | 1981-09-24 | Bayer Ag, 5090 Leverkusen | 2,6-Diamino-3,5-diäthoxycarbonyldihydropyridine, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel |
DE2406198C2 (de) * | 1974-02-09 | 1983-12-15 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von neuen 2-Amino-6-dialkylamino-dihydropyridinen |
JPS5922594U (ja) * | 1982-08-03 | 1984-02-10 | 日本マランツ株式会社 | 耳栓型ヘツドホ−ン |
JPS5922593U (ja) * | 1982-08-03 | 1984-02-10 | 日本マランツ株式会社 | ヘツドホ−ン用ホ−ン部取付構造 |
JPS6282898A (ja) * | 1985-10-08 | 1987-04-16 | Matsushita Electric Ind Co Ltd | ヘツドホン |
JPS6293060U (enrdf_load_stackoverflow) * | 1985-11-28 | 1987-06-13 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2210687C3 (de) * | 1972-03-06 | 1981-09-24 | Bayer Ag, 5090 Leverkusen | 2,6-Diamino-3,5-diäthoxycarbonyldihydropyridine, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel |
US3855231A (en) * | 1972-03-06 | 1974-12-17 | Bayer Ag | 2,6-diamino-1,4-dihydropyridine derivatives |
DE2406198C2 (de) * | 1974-02-09 | 1983-12-15 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von neuen 2-Amino-6-dialkylamino-dihydropyridinen |
-
1972
- 1972-03-06 DE DE2210687A patent/DE2210687C3/de not_active Expired
-
1973
- 1973-02-13 RO RO7300082647A patent/RO63068A/ro unknown
- 1973-02-13 RO RO73832A patent/RO61192A/ro unknown
- 1973-02-26 DD DD169048A patent/DD106833A5/xx unknown
- 1973-02-28 BG BG022858A patent/BG22815A3/xx unknown
- 1973-02-28 BG BG024472A patent/BG20583A3/xx unknown
- 1973-03-02 CH CH220176A patent/CH577473A5/xx not_active IP Right Cessation
- 1973-03-02 JP JP2445273A patent/JPS5626659B2/ja not_active Expired
- 1973-03-02 IL IL7341664A patent/IL41664A/en unknown
- 1973-03-02 CH CH313273A patent/CH580589A5/xx not_active IP Right Cessation
- 1973-03-02 FI FI657/73A patent/FI55996C/fi active
- 1973-03-02 LU LU67147A patent/LU67147A1/xx unknown
- 1973-03-03 PL PL1973182270A patent/PL92078B1/pl unknown
- 1973-03-03 PL PL1973161010A patent/PL89256B1/pl unknown
- 1973-03-05 CA CA165,209A patent/CA988524A/en not_active Expired
- 1973-03-05 ES ES412323A patent/ES412323A1/es not_active Expired
- 1973-03-05 SE SE7303021A patent/SE384208B/xx unknown
- 1973-03-05 IE IE346/73A patent/IE37370B1/xx unknown
- 1973-03-05 DK DK118073A patent/DK136061C/da active
- 1973-03-05 ZA ZA731501A patent/ZA731501B/xx unknown
- 1973-03-05 BE BE128374A patent/BE796279A/xx not_active IP Right Cessation
- 1973-03-05 KR KR7300356A patent/KR780000119B1/ko not_active Expired
- 1973-03-06 CS CS7500003602A patent/CS182792B2/cs unknown
- 1973-03-06 HU HUBA2892A patent/HU167089B/hu unknown
- 1973-03-06 FR FR7307923A patent/FR2181789B1/fr not_active Expired
- 1973-03-06 GB GB1075973A patent/GB1379005A/en not_active Expired
- 1973-03-06 AT AT925774*7A patent/AT327904B/de not_active IP Right Cessation
- 1973-03-06 AT AT925774A patent/ATA925774A/de unknown
- 1973-03-06 CS CS7300001593A patent/CS182781B2/cs unknown
- 1973-03-06 AT AT197373A patent/AT324338B/de not_active IP Right Cessation
- 1973-03-06 NL NL7303137A patent/NL7303137A/xx not_active Application Discontinuation
-
1980
- 1980-12-27 JP JP55185147A patent/JPS5911584B2/ja not_active Expired
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