DE2650013C3 - 1.4-Dihydro-2.6-dimethyl-4-(3-nitrophenyl)-3.5-pyridindicarbonsäureisopropyl-(2-propoxy-äthyl)-ester, Verfahren zu seiner Herstellung sowie ihn enthaltende Arzneimittel - Google Patents
1.4-Dihydro-2.6-dimethyl-4-(3-nitrophenyl)-3.5-pyridindicarbonsäureisopropyl-(2-propoxy-äthyl)-ester, Verfahren zu seiner Herstellung sowie ihn enthaltende ArzneimittelInfo
- Publication number
- DE2650013C3 DE2650013C3 DE2650013A DE2650013A DE2650013C3 DE 2650013 C3 DE2650013 C3 DE 2650013C3 DE 2650013 A DE2650013 A DE 2650013A DE 2650013 A DE2650013 A DE 2650013A DE 2650013 C3 DE2650013 C3 DE 2650013C3
- Authority
- DE
- Germany
- Prior art keywords
- ester
- formula
- propoxyethyl
- isopropyl
- acid
- 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 6
- 238000002360 preparation method Methods 0.000 title claims description 3
- BJZLZKZOTKFYIS-UHFFFAOYSA-N 5-o-propan-2-yl 3-o-(2-propoxyethyl) 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCCOCCOC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C)C1C1=CC=CC([N+]([O-])=O)=C1 BJZLZKZOTKFYIS-UHFFFAOYSA-N 0.000 title description 3
- 229940126601 medicinal product Drugs 0.000 title description 2
- -1 3-nitrophenyl Chemical group 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 14
- 239000003960 organic solvent Substances 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- ZETIVVHRRQLWFW-UHFFFAOYSA-N 3-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC(C=O)=C1 ZETIVVHRRQLWFW-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 229910021529 ammonia Inorganic materials 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- GVIIRWAJDFKJMJ-UHFFFAOYSA-N propan-2-yl 3-oxobutanoate Chemical compound CC(C)OC(=O)CC(C)=O GVIIRWAJDFKJMJ-UHFFFAOYSA-N 0.000 claims description 6
- BBBJXPCSKOPGLI-UHFFFAOYSA-N 2-propoxyethyl 3-oxobutanoate Chemical compound CCCOCCOC(=O)CC(C)=O BBBJXPCSKOPGLI-UHFFFAOYSA-N 0.000 claims description 5
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 claims description 4
- PBJZBRWKTBIWOK-FPLPWBNLSA-N 2-propoxyethyl (z)-3-aminobut-2-enoate Chemical compound CCCOCCOC(=O)\C=C(\C)N PBJZBRWKTBIWOK-FPLPWBNLSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 44
- 235000019441 ethanol Nutrition 0.000 description 18
- 229960001597 nifedipine Drugs 0.000 description 10
- HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 230000002093 peripheral effect Effects 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 230000036772 blood pressure Effects 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 5
- 230000017531 blood circulation Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 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
- 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
- 150000001298 alcohols Chemical class 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 230000005923 long-lasting effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 230000000304 vasodilatating effect Effects 0.000 description 3
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical class C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 241000049539 Bolbitis heteroclita Species 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 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
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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 2
- 241001465754 Metazoa Species 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 231100000673 dose–response relationship Toxicity 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 210000003141 lower extremity Anatomy 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 239000011435 rock Substances 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
- 239000007858 starting material Substances 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 230000002792 vascular Effects 0.000 description 2
- 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
- 241000251468 Actinopterygii Species 0.000 description 1
- 240000002470 Amphicarpaea bracteata Species 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- QMPBQBPWZICTEO-UHFFFAOYSA-N C(CC)OCCOC(C(=CC)N)=O Chemical compound C(CC)OCCOC(C(=CC)N)=O QMPBQBPWZICTEO-UHFFFAOYSA-N 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 239000004097 EU approved flavor enhancer Substances 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000006000 Knoevenagel condensation reaction Methods 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229910018540 Si C Inorganic materials 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 206010053648 Vascular occlusion Diseases 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- JCOLQKLSNIEXQL-UHFFFAOYSA-N acetonitrile;n-[bis(dimethylamino)phosphoryl]-n-methylmethanamine Chemical compound CC#N.CN(C)P(=O)(N(C)C)N(C)C JCOLQKLSNIEXQL-UHFFFAOYSA-N 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 208000029078 coronary artery disease Diseases 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
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 description 1
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 229960002428 fentanyl Drugs 0.000 description 1
- IVLVTNPOHDFFCJ-UHFFFAOYSA-N fentanyl citrate Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.C=1C=CC=CC=1N(C(=O)CC)C(CC1)CCN1CCC1=CC=CC=C1 IVLVTNPOHDFFCJ-UHFFFAOYSA-N 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 235000019264 food flavour enhancer Nutrition 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
- 239000012362 glacial acetic acid Substances 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
- 239000001257 hydrogen Substances 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 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
- 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
- 230000010412 perfusion Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 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
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000008159 sesame oil Substances 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
- 239000007787 solid Substances 0.000 description 1
- 239000008117 stearic acid Substances 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
- 230000035488 systolic blood pressure Effects 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
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 208000021331 vascular occlusion disease Diseases 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
- C07D211/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2650013A DE2650013C3 (de) | 1976-10-30 | 1976-10-30 | 1.4-Dihydro-2.6-dimethyl-4-(3-nitrophenyl)-3.5-pyridindicarbonsäureisopropyl-(2-propoxy-äthyl)-ester, Verfahren zu seiner Herstellung sowie ihn enthaltende Arzneimittel |
| US05/840,065 US4166855A (en) | 1976-10-30 | 1977-10-06 | 1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid ester, and its use as a peripheral vasodilator |
| GB44332/77A GB1568740A (en) | 1976-10-30 | 1977-10-25 | 1,4-dihydro-2,6 dimenthyl - 4 - (3 - nitrophenyl) - 3,5-pyridinendicarboxylic acid ester several processes for its preparation and its use as a peripheral vasodilator |
| CH1298277A CH633265A5 (de) | 1976-10-30 | 1977-10-25 | Verfahren zur herstellung des neuen 1.4-dihydro-2.6-dimethyl-4-(3-nitrophenyl)-3.5-pyridindicarbonsaeure-isopropyl-(2-propoxy-aethyl)-esters. |
| FI773208A FI60705C (fi) | 1976-10-30 | 1977-10-27 | Foerfarande foer framstaellning av 1,4-dihydro-2,6-dimetyl-4-(3-nitrofenyl)-3,5-pyridinkarboxylsyraisopropyl-(2-propoxi-etyl)-ester som anvaendes som perifer vasodilatator |
| SE7712108A SE433211B (sv) | 1976-10-30 | 1977-10-27 | Analogiforfarande for framstellning av 1,4-dehydro-2,6-dimetyl-4-(3-nitrofenyl)-3,5-pyridindikarbonsyra-isopropyl-(2-propoxietyl)-ester |
| NL7711827A NL7711827A (nl) | 1976-10-30 | 1977-10-27 | 1.4-dihydro-2.6-dimethyl-4-(3-nitrofenyl)- 3.5-pyridinedicarbonzuur-isopropyl-(2-pro- poxy-ethyl)ester, werkwijzen ter bereiding ervan, alsmede de toepassing als perifere vasodilatator. |
| AT773177A AT357162B (de) | 1976-10-30 | 1977-10-28 | Verfahren zur herstellung des neuen 1,4- dihydro-2,6-dimethyl-4- (3-nitrophenyl)-3,5- pyridindicarbonsaeure-isopropyl-(2-propoxy- aethyl)-esters |
| ES463646A ES463646A1 (es) | 1976-10-30 | 1977-10-28 | Procedimiento para la obtencion de 1,4-dihidro-2,6-dimetil- 4-(3-nitrofenil)-3,5-piridin-dicarboxilatos de isopropil-(2-propoxietilo). |
| CA289,781A CA1070314A (en) | 1976-10-30 | 1977-10-28 | 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridine-dicarboxylic acid ester, several processes for its preparation and its use as a peripheral vasodilator |
| JP12881477A JPS5356672A (en) | 1976-10-30 | 1977-10-28 | Production of 1*44dihydroo2*66 dimethyll44*33nitropheny**3*55 pyridinedicarroxylic acid ester and use of same as pepipherl blood vessel dilator |
| AU30147/77A AU507892B2 (en) | 1976-10-30 | 1977-10-28 | 1, 4-Dihydro-2, 6-dimethyl-4-(3-nitrophenyl)-3, 5 pyridine dicarboxylic acid isopropyl, 2-propoxyethy1 esters |
| FR7732558A FR2369264A1 (fr) | 1976-10-30 | 1977-10-28 | 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridine-dicarboxylate d'isopropyle et d |
| BE182159A BE860248A (fr) | 1976-10-30 | 1977-10-28 | 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridine-dicarboxylate d'isopropyle et de 2-propoxyethyle son procede de preparation et medicament vasodilatateur peripherique le contenant |
| CH754481A CH635078A5 (de) | 1976-10-30 | 1981-11-25 | Verfahren zur herstellung des neuen 1.4-dihydro-2.6-dimethyl-4-(3-nitrophenyl)-3.5-pyridindicarbonsaeure-isopropyl-(2-propoxy-aethyl)-esters. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2650013A DE2650013C3 (de) | 1976-10-30 | 1976-10-30 | 1.4-Dihydro-2.6-dimethyl-4-(3-nitrophenyl)-3.5-pyridindicarbonsäureisopropyl-(2-propoxy-äthyl)-ester, Verfahren zu seiner Herstellung sowie ihn enthaltende Arzneimittel |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2650013A1 DE2650013A1 (de) | 1978-05-11 |
| DE2650013B2 DE2650013B2 (de) | 1980-06-12 |
| DE2650013C3 true DE2650013C3 (de) | 1981-04-02 |
Family
ID=5992142
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2650013A Expired DE2650013C3 (de) | 1976-10-30 | 1976-10-30 | 1.4-Dihydro-2.6-dimethyl-4-(3-nitrophenyl)-3.5-pyridindicarbonsäureisopropyl-(2-propoxy-äthyl)-ester, Verfahren zu seiner Herstellung sowie ihn enthaltende Arzneimittel |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4166855A (enExample) |
| JP (1) | JPS5356672A (enExample) |
| AT (1) | AT357162B (enExample) |
| AU (1) | AU507892B2 (enExample) |
| BE (1) | BE860248A (enExample) |
| CA (1) | CA1070314A (enExample) |
| CH (2) | CH633265A5 (enExample) |
| DE (1) | DE2650013C3 (enExample) |
| ES (1) | ES463646A1 (enExample) |
| FI (1) | FI60705C (enExample) |
| FR (1) | FR2369264A1 (enExample) |
| GB (1) | GB1568740A (enExample) |
| NL (1) | NL7711827A (enExample) |
| SE (1) | SE433211B (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57175164A (en) * | 1981-04-18 | 1982-10-28 | Banyu Pharmaceut Co Ltd | 1,4-dihydropyridine derivative and its preparation |
| DE3208628A1 (de) * | 1982-03-10 | 1983-09-22 | Bayer Ag, 5090 Leverkusen | Neue verbindungen, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| JPS58185821U (ja) * | 1982-06-02 | 1983-12-10 | 日産自動車株式会社 | ウインドシ−ルド |
| DE3248548A1 (de) * | 1982-12-29 | 1984-07-05 | Heinrich Mack Nachf., 7918 Illertissen | Acylderivate von 1,4:3,6-dianhydro-hexiten, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| DE3316510A1 (de) * | 1983-05-06 | 1984-11-08 | Bayer Ag | Parenterale formulierung von nimodipin, ein verfahren zu ihrer herstellung sowie ihre verwendung bei der bekaempfung von erkrankungen |
| JPS60214778A (ja) * | 1984-03-08 | 1985-10-28 | Suntory Ltd | Ν置換３，４−ジヒドロピリミジン誘導体ならびにその製造法および用途 |
| DE3544692A1 (de) * | 1985-12-18 | 1987-06-19 | Bayer Ag | Dihydropyridinspray, verfahren zu seiner herstellung und seine pharmazeutische verwendung |
| LV12200B (lv) * | 1997-07-03 | 1999-04-20 | Gun�rs DUBURS | Antidiabētisks līdzeklis |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1670827C3 (de) * | 1967-03-20 | 1974-10-24 | Bayer Ag, 5090 Leverkusen | 4-(2'-Nitrophenyl)-2,6-dimethyl-3,5-dicarbmethoxy-1,4-dihydropyridin |
| DE2117571C3 (de) * | 1971-04-10 | 1979-10-11 | Bayer Ag, 5090 Leverkusen | Unsymmetrische 1,4-Dihydropyridin-33-dicarbonsäureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel |
| DE2117573C3 (de) * | 1971-04-10 | 1978-07-27 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von unsymmetrischen l,4-Dihydropyridin-3,5dicarbonsäureestern, sowie ihre Verwendung als Arzneimittel |
-
1976
- 1976-10-30 DE DE2650013A patent/DE2650013C3/de not_active Expired
-
1977
- 1977-10-06 US US05/840,065 patent/US4166855A/en not_active Expired - Lifetime
- 1977-10-25 GB GB44332/77A patent/GB1568740A/en not_active Expired
- 1977-10-25 CH CH1298277A patent/CH633265A5/de not_active IP Right Cessation
- 1977-10-27 FI FI773208A patent/FI60705C/fi not_active IP Right Cessation
- 1977-10-27 NL NL7711827A patent/NL7711827A/xx not_active Application Discontinuation
- 1977-10-27 SE SE7712108A patent/SE433211B/xx unknown
- 1977-10-28 AT AT773177A patent/AT357162B/de not_active IP Right Cessation
- 1977-10-28 AU AU30147/77A patent/AU507892B2/en not_active Expired
- 1977-10-28 JP JP12881477A patent/JPS5356672A/ja active Granted
- 1977-10-28 BE BE182159A patent/BE860248A/xx not_active IP Right Cessation
- 1977-10-28 ES ES463646A patent/ES463646A1/es not_active Expired
- 1977-10-28 FR FR7732558A patent/FR2369264A1/fr active Granted
- 1977-10-28 CA CA289,781A patent/CA1070314A/en not_active Expired
-
1981
- 1981-11-25 CH CH754481A patent/CH635078A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NL7711827A (nl) | 1978-05-03 |
| ES463646A1 (es) | 1978-07-16 |
| SE7712108L (sv) | 1978-05-01 |
| DE2650013B2 (de) | 1980-06-12 |
| FI60705B (fi) | 1981-11-30 |
| AU507892B2 (en) | 1980-02-28 |
| FR2369264A1 (fr) | 1978-05-26 |
| JPS5356672A (en) | 1978-05-23 |
| JPS577149B2 (enExample) | 1982-02-09 |
| AU3014777A (en) | 1979-05-03 |
| CH635078A5 (de) | 1983-03-15 |
| AT357162B (de) | 1980-06-25 |
| ATA773177A (de) | 1979-11-15 |
| SE433211B (sv) | 1984-05-14 |
| CH633265A5 (de) | 1982-11-30 |
| FI60705C (fi) | 1982-03-10 |
| GB1568740A (en) | 1980-06-04 |
| FI773208A7 (fi) | 1978-05-01 |
| FR2369264B1 (enExample) | 1980-06-13 |
| DE2650013A1 (de) | 1978-05-11 |
| BE860248A (fr) | 1978-04-28 |
| US4166855A (en) | 1979-09-04 |
| CA1070314A (en) | 1980-01-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |