FR2509727A1 - 2,6-dimethyl-3,5-dicarbomethoxy-4- (o-difluoromethylthiophenyl)- 1,4-dihydropyridine - Google Patents
2,6-dimethyl-3,5-dicarbomethoxy-4- (o-difluoromethylthiophenyl)- 1,4-dihydropyridine Download PDFInfo
- Publication number
- FR2509727A1 FR2509727A1 FR8212583A FR8212583A FR2509727A1 FR 2509727 A1 FR2509727 A1 FR 2509727A1 FR 8212583 A FR8212583 A FR 8212583A FR 8212583 A FR8212583 A FR 8212583A FR 2509727 A1 FR2509727 A1 FR 2509727A1
- Authority
- FR
- France
- Prior art keywords
- dihydropyridine
- compound
- dimethyl
- dicarbomethoxy
- difluoromethylthiophenyl
- 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.)
- Granted
Links
- SXDFGSZLXVWKIJ-UHFFFAOYSA-N dimethyl 4-[2-(difluoromethylsulfanyl)phenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1SC(F)F SXDFGSZLXVWKIJ-UHFFFAOYSA-N 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 27
- 230000001077 hypotensive effect Effects 0.000 abstract description 16
- 210000004351 coronary vessel Anatomy 0.000 abstract description 8
- 230000010339 dilation Effects 0.000 abstract description 7
- 230000002035 prolonged effect Effects 0.000 abstract description 5
- 239000000126 substance Substances 0.000 description 11
- ACZJZGLXRPZSLI-UHFFFAOYSA-N diethyl 2,6-dimethyl-4-[2-(trifluoromethyl)phenyl]-1,4-dihydropyridine-3,5-dicarboxylate Chemical group CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1C(F)(F)F ACZJZGLXRPZSLI-UHFFFAOYSA-N 0.000 description 9
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical class C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 description 8
- 241000282326 Felis catus Species 0.000 description 6
- 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 6
- -1 (o-trifluoromethylphenyl) -1,4-dihydropyridine Chemical compound 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 231100000053 low toxicity Toxicity 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- 208000001953 Hypotension Diseases 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 230000017531 blood circulation Effects 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- 210000000748 cardiovascular system Anatomy 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000001631 hypertensive effect Effects 0.000 description 2
- 208000021822 hypotensive Diseases 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 230000035488 systolic blood pressure Effects 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- VSXXEQVTFWPFAX-UHFFFAOYSA-N 1-(2-nitrophenyl)-4h-pyridine Chemical compound [O-][N+](=O)C1=CC=CC=C1N1C=CCC=C1 VSXXEQVTFWPFAX-UHFFFAOYSA-N 0.000 description 1
- RPJWCFQOPAHDKU-UHFFFAOYSA-N 2-(difluoromethyl)thiobenzaldehyde Chemical compound FC(F)C1=CC=CC=C1C=S RPJWCFQOPAHDKU-UHFFFAOYSA-N 0.000 description 1
- NOTFZGFABLVTIG-UHFFFAOYSA-N Cyclohexylethyl acetate Chemical compound CC(=O)OCCC1CCCCC1 NOTFZGFABLVTIG-UHFFFAOYSA-N 0.000 description 1
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical compound CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000916 dilatatory effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 229960001597 nifedipine Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000011699 spontaneously hypertensive rat Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 210000005166 vasculature Anatomy 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
- 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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU3353822 | 1981-07-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2509727A1 true FR2509727A1 (fr) | 1983-01-21 |
| FR2509727B1 FR2509727B1 (enExample) | 1984-10-26 |
Family
ID=20982471
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8212583A Granted FR2509727A1 (fr) | 1981-07-20 | 1982-07-19 | 2,6-dimethyl-3,5-dicarbomethoxy-4- (o-difluoromethylthiophenyl)- 1,4-dihydropyridine |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4435574A (enExample) |
| JP (1) | JPS5841866A (enExample) |
| DE (1) | DE3226922C2 (enExample) |
| FR (1) | FR2509727A1 (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3314362A1 (de) * | 1983-01-12 | 1984-10-25 | Institut organičeskogo sinteza Akademii Nauk Latvijskoj SSR, Riga | 2,6-dimethyl-3,5-bis-(1-adamantyloxykarbonyl)-4-(2-difluormethoxyphenyl)-1,4-dyhydropyridin |
| US4492703A (en) * | 1982-03-05 | 1985-01-08 | Bayer Aktiengesellschaft | 4-(2-Substituted phenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid esters active on blood circulation |
| WO1988003529A1 (fr) * | 1986-11-10 | 1988-05-19 | Institut Organicheskogo Sinteza Akademii Nauk Latv | 2-methylmercapto-3-cyano-4-(o-difluoromethoxyphenyle)-6-phenyle-1,4-dihydropyridine |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4738965A (en) * | 1987-02-03 | 1988-04-19 | Institut Organischskogo Sinteza Akademii Nauk Ssr | 2-oxo-4-(2'-difluoromethylthiophenyl)-5-methoxycarbonyl-6-methyl-1,2,3,4-tetrahydropyrimidine |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1574702A (enExample) * | 1967-02-07 | 1969-07-18 | ||
| FR2414501A1 (fr) * | 1978-01-11 | 1979-08-10 | Inst Organicheskogo Sinteza Ak | 2,6-dimethyl-3,5-dimethoxycarbonyl-4-(o-difluoromethoxyphenyl)-1,4-dihydropyridine |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3968117A (en) | 1972-06-10 | 1976-07-06 | Bayer Aktiengesellschaft | 1,4-Dihydropyridines |
-
1982
- 1982-07-16 US US06/398,910 patent/US4435574A/en not_active Expired - Fee Related
- 1982-07-19 FR FR8212583A patent/FR2509727A1/fr active Granted
- 1982-07-19 DE DE3226922A patent/DE3226922C2/de not_active Expired
- 1982-07-20 JP JP57125216A patent/JPS5841866A/ja active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1574702A (enExample) * | 1967-02-07 | 1969-07-18 | ||
| FR2414501A1 (fr) * | 1978-01-11 | 1979-08-10 | Inst Organicheskogo Sinteza Ak | 2,6-dimethyl-3,5-dimethoxycarbonyl-4-(o-difluoromethoxyphenyl)-1,4-dihydropyridine |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4492703A (en) * | 1982-03-05 | 1985-01-08 | Bayer Aktiengesellschaft | 4-(2-Substituted phenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid esters active on blood circulation |
| DE3314362A1 (de) * | 1983-01-12 | 1984-10-25 | Institut organičeskogo sinteza Akademii Nauk Latvijskoj SSR, Riga | 2,6-dimethyl-3,5-bis-(1-adamantyloxykarbonyl)-4-(2-difluormethoxyphenyl)-1,4-dyhydropyridin |
| WO1988003529A1 (fr) * | 1986-11-10 | 1988-05-19 | Institut Organicheskogo Sinteza Akademii Nauk Latv | 2-methylmercapto-3-cyano-4-(o-difluoromethoxyphenyle)-6-phenyle-1,4-dihydropyridine |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5841866A (ja) | 1983-03-11 |
| FR2509727B1 (enExample) | 1984-10-26 |
| DE3226922A1 (de) | 1983-05-26 |
| US4435574A (en) | 1984-03-06 |
| DE3226922C2 (de) | 1984-10-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |