CA1085406A - Isobutyl methyl-1,4-dihydro-2,6-dimethyl-4-(2- nitrophenyl)-3,5-pyridindicarboxylate - Google Patents
Isobutyl methyl-1,4-dihydro-2,6-dimethyl-4-(2- nitrophenyl)-3,5-pyridindicarboxylateInfo
- Publication number
- CA1085406A CA1085406A CA264,921A CA264921A CA1085406A CA 1085406 A CA1085406 A CA 1085406A CA 264921 A CA264921 A CA 264921A CA 1085406 A CA1085406 A CA 1085406A
- Authority
- CA
- Canada
- Prior art keywords
- ester
- formula
- isobutyl
- dihydro
- dimethyl
- 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
- FRLYQVMOWHLNET-UHFFFAOYSA-N 1,2,6-trimethyl-5-(2-methylpropoxycarbonyl)-4-(2-nitrophenyl)-4H-pyridine-3-carboxylic acid Chemical compound CC(C)COC(=O)C1=C(C)N(C)C(C)=C(C(O)=O)C1C1=CC=CC=C1[N+]([O-])=O FRLYQVMOWHLNET-UHFFFAOYSA-N 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 19
- -1 1,4-dihydropyridine-3,5-dicarboxylic acid di-ester Chemical class 0.000 claims abstract description 11
- VKQFCGNPDRICFG-UHFFFAOYSA-N methyl 2-methylpropyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCC(C)C)C1C1=CC=CC=C1[N+]([O-])=O VKQFCGNPDRICFG-UHFFFAOYSA-N 0.000 claims abstract 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 47
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 11
- 238000010992 reflux Methods 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- ZYXNLVMBIHVDRH-UHFFFAOYSA-N 2-Methylpropyl 3-oxobutanoate Chemical compound CC(C)COC(=O)CC(C)=O ZYXNLVMBIHVDRH-UHFFFAOYSA-N 0.000 claims description 7
- CMWKITSNTDAEDT-UHFFFAOYSA-N 2-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC=C1C=O CMWKITSNTDAEDT-UHFFFAOYSA-N 0.000 claims description 7
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 claims description 7
- 229910021529 ammonia Inorganic materials 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- CJBFCOOECPQZDM-VOTSOKGWSA-N methyl (e)-5-(2-nitrophenyl)-3-oxopent-4-enoate Chemical compound COC(=O)CC(=O)\C=C\C1=CC=CC=C1[N+]([O-])=O CJBFCOOECPQZDM-VOTSOKGWSA-N 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 5
- ZYVYEJXMYBUCMN-UHFFFAOYSA-N 1-methoxy-2-methylpropane Chemical group COCC(C)C ZYVYEJXMYBUCMN-UHFFFAOYSA-N 0.000 claims description 3
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 239000003814 drug Substances 0.000 abstract description 21
- 150000001875 compounds Chemical class 0.000 abstract description 20
- 238000002360 preparation method Methods 0.000 abstract description 7
- 229940124597 therapeutic agent Drugs 0.000 abstract description 3
- 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 abstract description 2
- 239000003085 diluting agent Substances 0.000 description 18
- 235000019441 ethanol Nutrition 0.000 description 14
- 239000008194 pharmaceutical composition Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
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- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical class C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 description 4
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- 239000008298 dragée Substances 0.000 description 4
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229920001615 Tragacanth Polymers 0.000 description 2
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- 235000010419 agar Nutrition 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
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- 239000000499 gel Substances 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
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- 239000002674 ointment Substances 0.000 description 2
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- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
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- BUHJNRJEBAWMIF-DAXSKMNVSA-N 2-methylpropyl (Z)-2-aminobut-2-enoate Chemical compound C(C(C)C)OC(\C(=C\C)\N)=O BUHJNRJEBAWMIF-DAXSKMNVSA-N 0.000 description 1
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
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- JCYZMTMYPZHVBF-UHFFFAOYSA-N Melarsoprol Chemical compound NC1=NC(N)=NC(NC=2C=CC(=CC=2)[As]2SC(CO)CS2)=N1 JCYZMTMYPZHVBF-UHFFFAOYSA-N 0.000 description 1
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- 235000019483 Peanut oil Nutrition 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
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- 241001201614 Prays Species 0.000 description 1
- 101150107341 RERE gene Proteins 0.000 description 1
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- VJHCJDRQFCCTHL-UHFFFAOYSA-N acetic acid 2,3,4,5,6-pentahydroxyhexanal Chemical class CC(O)=O.OCC(O)C(O)C(O)C(O)C=O VJHCJDRQFCCTHL-UHFFFAOYSA-N 0.000 description 1
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- 150000001299 aldehydes Chemical class 0.000 description 1
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- 239000004411 aluminium Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
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- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
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- 239000003708 ampul Substances 0.000 description 1
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- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
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- SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
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- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
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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
-
- 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
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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP2549568.5 | 1975-11-05 | ||
| DE2549568A DE2549568C3 (de) | 1975-11-05 | 1975-11-05 | 2,6-Dimethyl-3-methoxycarbonyl-4- (2'-nitrophenyl)-1,4-dihydropyridin-5- carbonsäureisobutylester, mehrere Verfahren zu seiner Herstellung sowie ihn enthaltende Arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1085406A true CA1085406A (en) | 1980-09-09 |
Family
ID=5960951
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA264,921A Expired CA1085406A (en) | 1975-11-05 | 1976-11-04 | Isobutyl methyl-1,4-dihydro-2,6-dimethyl-4-(2- nitrophenyl)-3,5-pyridindicarboxylate |
Country Status (27)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4146630A (en) * | 1976-11-12 | 1979-03-27 | Boehringer Mannheim Gmbh | Blood pressure lowering and adrenergic β-receptor inhibiting 3-(4-phenoxymethylpiperidino)-propyl-phenyl ethers |
| JPS55301A (en) * | 1978-02-14 | 1980-01-05 | Yamanouchi Pharmaceut Co Ltd | 1,4-dihydropyridine-3,5-dicarboxylic ester derivative and its preparation |
| DE3212736A1 (de) * | 1982-04-06 | 1983-10-13 | Bayer Ag, 5090 Leverkusen | Verwendung von dihydropyridinen in arzneimitteln mit salidiuretischer wirkung |
| DE3222367A1 (de) * | 1982-06-15 | 1983-12-15 | Bayer Ag, 5090 Leverkusen | Verwendung von 1,4-dihydropyridinen in antiarteriosklerotika und deren herstellung |
| JPS5982192U (ja) * | 1982-11-27 | 1984-06-02 | エムケ−精工株式会社 | 扉 |
| DE3312283A1 (de) * | 1983-04-05 | 1984-10-18 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von unsymmetrischen 1,4-dihydropyridincarbonsaeureestern |
| DE3312216A1 (de) * | 1983-04-05 | 1984-10-11 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von symmetrischen 1,4-dihydropyridincarbonsaeureestern |
| US4794111A (en) * | 1984-05-23 | 1988-12-27 | Bayer Aktiengesellschaft | Dihydropyridine preparations containing β-blockers |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
-
1975
- 1975-11-05 DE DE2549568A patent/DE2549568C3/de not_active Expired
-
1976
- 1976-10-22 NO NO763608A patent/NO145574C/no unknown
- 1976-10-29 JP JP51129540A patent/JPS5259161A/ja active Granted
- 1976-11-01 BG BG035341A patent/BG25078A3/xx unknown
- 1976-11-01 BG BG034575A patent/BG24668A3/xx unknown
- 1976-11-01 BG BG035344A patent/BG24804A3/xx unknown
- 1976-11-01 BG BG035345A patent/BG24805A3/xx unknown
- 1976-11-01 BG BG035343A patent/BG24803A3/xx unknown
- 1976-11-01 BG BG035342A patent/BG25079A3/xx unknown
- 1976-11-02 IL IL50817A patent/IL50817A/xx unknown
- 1976-11-02 CS CS767068A patent/CS200499B2/cs unknown
- 1976-11-02 CH CH1381976A patent/CH623038A5/de not_active IP Right Cessation
- 1976-11-02 NZ NZ182502A patent/NZ182502A/xx unknown
- 1976-11-02 RO RO7688294A patent/RO70295A/ro unknown
- 1976-11-02 GB GB45501/76A patent/GB1516793A/en not_active Expired
- 1976-11-03 NL NLAANVRAGE7612198,A patent/NL175915C/xx not_active IP Right Cessation
- 1976-11-03 AT AT814276A patent/AT352129B/de not_active IP Right Cessation
- 1976-11-03 PL PL1976201800A patent/PL105940B1/pl unknown
- 1976-11-03 FI FI763160A patent/FI60704C/fi not_active IP Right Cessation
- 1976-11-03 PL PL1976193438A patent/PL106084B1/pl unknown
- 1976-11-04 IE IE2458/76A patent/IE43984B1/en not_active IP Right Cessation
- 1976-11-04 LU LU88275C patent/LU88275I2/xx unknown
- 1976-11-04 CA CA264,921A patent/CA1085406A/en not_active Expired
- 1976-11-04 GR GR52093A patent/GR61241B/el unknown
- 1976-11-04 BE BE172063A patent/BE847968A/xx not_active IP Right Cessation
- 1976-11-04 PT PT65797A patent/PT65797B/pt unknown
- 1976-11-04 LU LU76133A patent/LU76133A1/xx active Protection Beyond IP Right Term
- 1976-11-04 ES ES452986A patent/ES452986A1/es not_active Expired
- 1976-11-04 ZA ZA766622A patent/ZA766622B/xx unknown
- 1976-11-04 SE SE7612308A patent/SE423542B/xx not_active IP Right Cessation
- 1976-11-04 DK DK498476A patent/DK146762C/da not_active IP Right Cessation
- 1976-11-05 FR FR7633488A patent/FR2330395A1/fr active Granted
- 1976-11-05 AU AU19358/76A patent/AU498964B2/en not_active Expired
-
1977
- 1977-10-13 ES ES463166A patent/ES463166A1/es not_active Expired
-
1980
- 1980-07-23 CH CH567880A patent/CH622779A5/de not_active IP Right Cessation
-
1981
- 1981-04-02 HK HK126/81A patent/HK12681A/xx unknown
-
1993
- 1993-05-24 NL NL930035C patent/NL930035I2/nl unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |