DK178584A - METHOD OF PREPARING SYMMETRIC 1,4-DIHYDROPYRIDINES - Google Patents
METHOD OF PREPARING SYMMETRIC 1,4-DIHYDROPYRIDINES Download PDFInfo
- Publication number
- DK178584A DK178584A DK178584A DK178584A DK178584A DK 178584 A DK178584 A DK 178584A DK 178584 A DK178584 A DK 178584A DK 178584 A DK178584 A DK 178584A DK 178584 A DK178584 A DK 178584A
- Authority
- DK
- Denmark
- Prior art keywords
- formula
- see diagramm
- dihydropyridines
- degrees
- compound
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Manufacture Of Tobacco Products (AREA)
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Diaphragms For Electromechanical Transducers (AREA)
- Magnetic Ceramics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
- Air Supply (AREA)
Abstract
1. Processs for the preparation of symmetrical 1,4-dihydropyridines of the formula I see diagramm : EP0124742,P6,F1 in which R represents a phenyl radical which is optionally mono- or disubstituted by nitro and/or chlorine, and R1 represents a C1 -C4 -alkyl radical which is optionally substituted by a C1 -C4 -alkoxy group, by reaction of an ylidene compound of the formula II see diagramm : EP0124742,P6,F2 with an enamine compound of the formula III see diagramm : EP0124742,P6,F3 characterized in that the ylidene compound of the formula II is prepared by reaction of a ketocarboxylic ester of the formula IV see diagramm : EP0124742,P6,F4 with an aldehyde of the formula RCHO in a solvent, in the presence of catalytic amounts of piperidine acetate, at temperatures from - 10 degrees C and up to 100 degrees C.
Description
med en enaminforbindeIse med formlenwith an enamine compound of formula
(III) idet ylidenforbindelsen (II) fremstilles ved omsætning af en ketocarboxylsyreester med formlen(III) wherein the ylidene compound (II) is prepared by reacting a ketocarboxylic acid ester of the formula
(IV) med et aldehyd RCHO i et opløsningsmiddel i nærværelse af katalytiske mængder af acetatsalte af aminer ved temperaturer fra -10°C til 100°C.(IV) with an aldehyde RCHO in a solvent in the presence of catalytic amounts of acetate salts of amines at temperatures from -10 ° C to 100 ° C.
Forbindelserne (I) fås herved i stort udbytte og med høj renhedsgrad.The compounds (I) are thus obtained in high yield and high purity.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3312216 | 1983-04-05 | ||
| DE3312216A DE3312216A1 (en) | 1983-04-05 | 1983-04-05 | METHOD FOR PRODUCING SYMMETRIC 1,4-DIHYDROPYRIDINE CARBONIC ACID ESTERS |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| DK178584D0 DK178584D0 (en) | 1984-04-04 |
| DK178584A true DK178584A (en) | 1984-10-06 |
| DK160488B DK160488B (en) | 1991-03-18 |
| DK160488C DK160488C (en) | 1991-08-26 |
Family
ID=6195495
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK178584A DK160488C (en) | 1983-04-05 | 1984-04-04 | METHOD OF PREPARING SYMMETRIC 1,4-DIHYDROPYRIDINES |
Country Status (18)
| Country | Link |
|---|---|
| EP (1) | EP0124742B1 (en) |
| JP (1) | JPH0662564B2 (en) |
| KR (2) | KR900004038B1 (en) |
| AT (1) | ATE36849T1 (en) |
| AU (1) | AU558122B2 (en) |
| CA (1) | CA1234573A (en) |
| DE (2) | DE3312216A1 (en) |
| DK (1) | DK160488C (en) |
| ES (1) | ES531236A0 (en) |
| FI (1) | FI78471C (en) |
| GR (1) | GR81898B (en) |
| HU (1) | HU192546B (en) |
| IE (1) | IE57181B1 (en) |
| IL (1) | IL71425A (en) |
| NO (1) | NO166178C (en) |
| PH (1) | PH20992A (en) |
| PT (1) | PT78365B (en) |
| ZA (1) | ZA842510B (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3312283A1 (en) * | 1983-04-05 | 1984-10-18 | Bayer Ag, 5090 Leverkusen | METHOD FOR PRODUCING UNBALANCED 1,4-DIHYDROPYRIDINE CARBONIC ACID ESTERS |
| DE3508533A1 (en) * | 1985-03-09 | 1986-09-11 | Bayer Ag, 5090 Leverkusen | METHOD FOR PRODUCING BENZYLIDE COMPOUNDS |
| US4771057A (en) * | 1986-02-03 | 1988-09-13 | University Of Alberta | Reduced pyridyl derivatives with cardiovascular regulating properties |
| DE4423445A1 (en) * | 1994-07-05 | 1996-01-11 | Bayer Ag | Rapid high yield prodn. of nifedipin |
| DE19727350C1 (en) * | 1997-06-27 | 1999-01-21 | Bayer Ag | Process for the preparation of nifedipine |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1792764C3 (en) * | 1967-03-20 | 1981-04-23 | Bayer Ag, 5090 Leverkusen | Coronary drugs |
| DE1670824C3 (en) * | 1967-03-20 | 1978-08-03 | Bayer Ag, 5090 Leverkusen | 1,4-Dihydropyridine-33-dicarboxylic acid alkyl ester |
| DE2335466A1 (en) * | 1973-07-12 | 1975-01-30 | Bayer Ag | ALCOXY ALKYL-1,4-DIHYDROPYRIDINE, THE METHOD FOR THEIR MANUFACTURING AND THEIR USE AS A MEDICINAL PRODUCT |
| US4370334A (en) * | 1975-07-02 | 1983-01-25 | Fujisawa Pharmaceutical Co., Ltd. | 1,4-Dihydro-pyridine derivatives and methods of using same |
| DE2549568C3 (en) * | 1975-11-05 | 1981-10-29 | Bayer Ag, 5090 Leverkusen | 2,6-Dimethyl-3-methoxycarbonyl-4- (2'-nitrophenyl) -1,4-dihydropyridine-5-carboxylic acid isobutyl ester, several processes for its preparation and pharmaceuticals containing it |
| JPS5936896B2 (en) * | 1976-10-21 | 1984-09-06 | 住友化学工業株式会社 | α-acetyl cinnamic acid ester derivatives, their production methods, and herbicides comprising the compounds |
| CA1117117A (en) * | 1978-10-10 | 1982-01-26 | Fujisawa Pharmaceutical Co., Ltd. | 2-methyl-dihydropyridine compound, processes for preparation thereof and pharmaceutical composition comprising the same |
| JPS5529990A (en) * | 1979-03-19 | 1980-03-03 | Wako Pure Chem Ind Ltd | Activity measurement of monoamine oxidase (mao) |
-
1983
- 1983-04-05 DE DE3312216A patent/DE3312216A1/en not_active Withdrawn
-
1984
- 1984-03-22 NO NO841142A patent/NO166178C/en not_active IP Right Cessation
- 1984-03-26 EP EP84103304A patent/EP0124742B1/en not_active Expired
- 1984-03-26 DE DE8484103304T patent/DE3473756D1/en not_active Expired
- 1984-03-26 AT AT84103304T patent/ATE36849T1/en not_active IP Right Cessation
- 1984-04-02 JP JP59063438A patent/JPH0662564B2/en not_active Expired - Lifetime
- 1984-04-02 IL IL71425A patent/IL71425A/en not_active IP Right Cessation
- 1984-04-03 PH PH30491A patent/PH20992A/en unknown
- 1984-04-03 ES ES531236A patent/ES531236A0/en active Granted
- 1984-04-03 CA CA000451158A patent/CA1234573A/en not_active Expired
- 1984-04-03 FI FI841336A patent/FI78471C/en not_active IP Right Cessation
- 1984-04-03 PT PT78365A patent/PT78365B/en unknown
- 1984-04-03 GR GR74294A patent/GR81898B/el unknown
- 1984-04-04 KR KR1019840001767A patent/KR900004038B1/en not_active Expired
- 1984-04-04 DK DK178584A patent/DK160488C/en not_active IP Right Cessation
- 1984-04-04 IE IE828/84A patent/IE57181B1/en not_active IP Right Cessation
- 1984-04-04 ZA ZA842510A patent/ZA842510B/en unknown
- 1984-04-04 AU AU26416/84A patent/AU558122B2/en not_active Expired
- 1984-04-04 KR KR1019840001767A patent/KR840008647A/en active Granted
- 1984-04-05 HU HU841337A patent/HU192546B/en unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUP | Patent expired |