US3887558A
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US
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Process for producing 2,6-diamino -1,4- dihydro-3,5-pyridine-dicarboxylates and derivatives thereof
Assignee: Bayer AG
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Filing: 1974-03-27
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Granted: 1975-06-03
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Expires: 1994-03-27
Abstract
Abstract 2,6-Diamino-1,4-dihydropyridines bearing carbonyl functions in the 3- and 5-positions and being substituted in the 4-position by lower alkyl, phenyl, substituted phenyl or a heterocyclic group are antihypertensive agents and coronary vessel dilators. The compounds, of which 2,6-diamino-4-(3-nitrophenyl)-1,4dihydropyridine-3,5-dicarboxylic acid 3,5-diethyl ester is a representative embodiment, are prepared through condensation of an amidine with either an aldehyde or an ylidenecyanoacetoacetic acid ester.
Inventors
- 👤 Horst Meyer
- 👤 Friedrich Bossert
- 👤 Wulf Vater
- 👤 Kurt Stoepel
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 07:45
CPC Classifications
C; C07; C07D; C07D401/00; C07D401/02; C07D401/04; A; A61; A61K; A61K31/00; A61K31/33; A61K31/395; A61K31/435; A61K31/44; A61K31/455; C07D211/00; C07D211/04; C07D211/80; C07D211/84; C07D211/90; C07D405/00; C07D405/02; C07D405/04
Claims Analysis
Total Claims: 35
Claim 1
Independent Claim
11 words
A PROCESS FOR THE PRODUCTION OF A COMPOUND OF THE FORMULA
Claim 2
Dependent Claim
11 words
A PROCESS FOR THE PRODUCTION OF A COMPOUND OF THE FORMULA
Claim 3
Dependent Claim
11 words
A process for the production of a compound of the formula
Claim 4
Dependent Claim
11 words
A process for the production of a compound of the formula
Claim 5
Dependent Claim
13 words
A process according to claim 1 wherein R1 and R2 are lower alkoxy.
Claim 6
Dependent Claim
37 words
A process according to claim 2 wherein R is quinolyl, isoquinolyl, pyridyl, pyrimidyl, phenyl, furyl or pyrryl, unsubstituted or substituted by 1 or 2 members selected from the group consisting of lower alkyl, lower alkoxy and halogeno.
Claim 7
Dependent Claim
47 words
A process according to claim 2 wherein R is lower alkyl, naphthyl, phenyl, bi-phenyl, or phenyl substituted with from one to three substituents selected from the group consisting of lower alkyl, lower alkoxy, halogeno, nitro, cyano, trifluoromethyl, azido, carb(lower alkoxy), lower alkylsulfonyl, lower alkylsulfinyl and lower alkylthio.
Claim 8
Dependent Claim
14 words
A process according to claim 1 wherein the alkali metal alkoxide is sodium methoxide.
Claim 9
Dependent Claim
26 words
A process according to claim 1 wherein the inert organic solvent is methanol, ethanol, propanol, dioxane, diethyl ether, glacial acetic acid, pyridine, dimethylformamide, dimethylsulphoxide or acetonitrile.
Claim 10
Dependent Claim
17 words
A process according to claim 1 wherein the reaction temperature is the boiling point of the solvent.
Claim 11
Dependent Claim
25 words
A process according to claim 1 wherein the reactants are employed in substantially equimolar amounts when the amidine is reacted with the ylidene cyanoacetic acid.
Claim 12
Dependent Claim
22 words
A process according to claim 1 wherein at least two molar equivalents of amidine are employed per molar equivalent of aldehyde reactant.
Claim 13
Dependent Claim
38 words
The process according to claim 1 wherein 2,6-diamino-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester is produced by reacting amidinoacetic acid ethyl ester and benzaldehyde in the presence of ethanol at the boiling point of the solution and recovering the compound produced.
Claim 14
Dependent Claim
38 words
The process according to claim 1 wherein 2,6-diamino-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester is produced by reacting amidinoacetic acid ethyl ester and 2-nitrobenzaldehyde in the presence of ethanol at the boiling point of the solution and recovering the compound produced.
Claim 15
Dependent Claim
38 words
The process according to claim 1 wherein 2,6-diamino-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester is produced by reacting amidinoacetic acid ethyl ester and 3-nitrobenzaldehyde in the presence of ethanol at the boiling point of the solution and recovering the compound produced.
Claim 16
Dependent Claim
38 words
The process according to claim 1 wherein 2,6-diamino-4-(3-cyanophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester is produced by reacting amidinoacetic acid ethyl ester and 3-cyanobenzaldehyde in the presence of ethanol at the boiling point of the solution and recovering the compound produced.
Claim 17
Dependent Claim
38 words
The process according to claim 1 wherein 2,6-diamino-4-(2-methylphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester is produced by reacting amidinoacetic acid ethyl ester and 2-methylbenzaldehyde in the presence of ethanol at the boiling point of the solution and recovering the compound produced.
Claim 18
Dependent Claim
38 words
The process according to claim 1 wherein 2,6-diamino-4-(2-methoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester is produced by reacting amidinoacetic acid ethyl ester and 2-methoxybenzaldehyde in the presence of ethanol at the boiling point of the solution and recovering the compound produced.
Claim 19
Dependent Claim
38 words
The process according to claim 1 wherein 2,6-diamino-4-(2-fluorophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester is produced by reacting amidinoacetic acid ethyl ester and 2-fluorobenzaldehyde in the presEnce of ethanol at the boiling point of the solution and recovering the compound produced.
Claim 20
Dependent Claim
38 words
The process according to claim 1 wherein 2,6-diamino-4-(2-trifluoromethylphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester is produced by reacting amidinoacetic acid ethyl ester and 2-trifluoromethylbenzaldehyde in the presence of ethanol at the boiling point of the solution and recovering the compound produced.
Claim 21
Dependent Claim
38 words
The process according to claim 1 wherein 2,6-diamino-4-(3-trifluoromethylphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester is produced by reacting amidinoacetic acid ethyl ester and 3-trifluoromethylbenzaldehyde in the presence of ethanol at the boiling point of the solution and recovering the compound produced.
Claim 22
Dependent Claim
38 words
The process according to claim 1 wherein 2,6-diamino-4-methyl-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester is produced by reacting amidinoacetic acid ethyl ester and acetaldehyde in the presence of ethanol at the boiling point of the solution and recovering the compound produced.
Claim 23
Dependent Claim
38 words
The process according to claim 1 wherein 2,6-diamino-4-(3-nitro-6-chlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester is produced by reacting amidinoacetic acid ethyl ester and 3-nitro-6-chlorobenzaldehyde in the presence of ethanol at the boiling point of the solution and recovering the compound produced.
Claim 24
Dependent Claim
41 words
The process according to claim 1 wherein 2,6-diamino-4-( Alpha -pyridyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester is produced by reacting amidinoacetic acid ethyl ester and Alpha -pyridinaldehyde in the presence of ethanol at the boiling point of the solution and recovering the compound produced.
Claim 25
Dependent Claim
39 words
The process according to claim 1 wherein 2,6-diamino-4-(4,6-dimethoxypyrimid-5-yl)-1,4-dihydropyridine-3,5 -dicarboxylic acid diethyl ester is produced by reacting amidinoacetic acid ethyl ester and 4,6-dimethoxypyrimidine-5-aldehyde in the presence of ethanol at the boiling point of the solution and recovering the compound produced.
Claim 26
Dependent Claim
38 words
The process according to claim 1 wherein 2,6-diamino-4-(furyl-2)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester is produced by reacting amidinoacetic acid ethyl ester and furan-2-aldehyde in the presence of ethanol at the boiling point of the solution and recovering the compound produced.
Claim 27
Dependent Claim
38 words
The process according to claim 1 wherein 2,6-diamino-4-(naphth-1-yl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester is produced by reacting amidinoacetic acid ethyl ester and 1-naphthaldehyde in the presence of ethanol at the boiling point of the solution and recovering the compound produced.
Claim 28
Dependent Claim
38 words
The process according to claim 1 wherein 2,6-diamino-4-(quinol-4-yl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester is produced by reacting amidinoacetic acid ethyl ester and quinoline-4-aldehyde in the presence of ethanol at the boiling point of the solution and recovering the compound produced.
Claim 29
Dependent Claim
38 words
The process according to claim 1 wherein 2,6-diamino-4-(4-methylmercaptophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester is produced by reacting amidinoacetic acid ethyl ester and 4-methylmercaptobenzaldehyde in the presence of ethanol at the boiling point of the solution and recovering the compound produced.
Claim 30
Dependent Claim
38 words
The process according to claim 1 wherein 2,6-diamino-4-(biphenyl-2-yl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester is produced by reacting amidinoacetic acid ethyl ester and biphenyl-2-aldehyde in the presence of ethanol at the boiling point of the solution and recovering the compound produced.
Claim 31
Dependent Claim
38 words
The process accordIng to claim 1 wherein 2,6-diamino-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid dipropargyl ester is produced by reacting amidinoacetic acid propargyl ester and nitrobenzaldehyde in the presence of ethanol at the boiling point of the solution and recovering the compound produced.
Claim 32
Dependent Claim
38 words
The process according to claim 1 wherein 2,6-diamino-4-(pyrid-4-yl)-1,4-dihydropyridine-3,5-dicarboxylic acid diisopropyl ester is produced by reacting amidinoacetic acid isopropyl ester and pyridine-4-aldehyde in the presence of ethanol at the boiling point of the solution and recovering the compound produced.
Claim 33
Dependent Claim
39 words
The process according to claim 1 wherein 2,6-diamino-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylic acid 3-ethyl ester 5-isopropyl ester is produced by reacting amidinoacetic acid isopropyl ester and benzylidenecyanoacetic acid ethyl ester in ethanol in the presence of sodium ethylate and recovering the compound produced.
Claim 34
Dependent Claim
38 words
The process according to claim 1 wherein 2,6-diamino-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid-3-isopropyl ester 5-ethyl ester is produced by reacting amidinoacetic acid isopropyl ester and 2-nitrobenzylidenecyanoacetic acid ethyl ester in ethanol in the presence of sodium ethylate and recovering the compound produced.
Claim 35
Dependent Claim
38 words
The process according to claim 1 wherein 2,6-diamino-4-(2-azidophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester is produced by reacting amidinoacetic acid ethyl ester and 2-azidobenzaldehyde in the presence of ethanol at the boiling point of the solution and recovering the compound produced.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1978-06-02 | 1978-12-02 | 1979-06-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-06-02 | 1982-12-02 | 1983-06-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-06-02 | 1986-12-02 | 1987-06-03 | $7700.00 | Window Closed / Lapsed |