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US3696112A Expired / Lapsed US ⏱️ 0.0 years remaining

Sulphur-containing 1,4-dihydropyridine derivatives

Assignee: Bayer AG
•
Filing: 1970-11-20
•
Granted: 1972-10-03
•
Expires: 1990-11-20
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Abstract

Abstract Sulphur-containing 1,4-dihydropyridine derivatives of the formula: D R A W I N G WHEREIN R is hydrogen, saturated or unsaturated, straight, branched or cyclic alkyl of one to six carbon atoms, unsubstituted or substituted by hydroxyl or alkoxy of one to three carbon atoms, or benzyl or phenethyl unsubstituted or substituted in the aryl moiety by one, two or three members selected from the group consisting of one to three alkoxy moieties of one to three carbon atoms, one or two alkyl moieties of one to three carbon atoms and one to two halogen atoms, R'' is straight or branched chain alkyl of one to four carbon atoms, R'''' is straight, branched, cyclic, saturated or unsaturated alkyl of one to six carbon atoms, said alkyl interrupted by one or two oxygen atoms or said alkyl substituted by hydroxyl, R'''''' is aryl substituted by SOnR1, unsubstituted or substituted by one to eight members selected from the group consisting of nitro, amino, acylamino of one to two carbon atoms, hydroxyl, acyloxy of one to two carbon atoms, one or two alkyl moieties of one to four carbon atoms, one or two alkoxy moieties of one to four carbon atoms, and one or two halogen atoms, N IS 0, 1, 2 OR 3, AND R1 is lower alkyl of one to four carbon atoms or phenyl when n is 0, 1 or 2 and R1 is hydrogen when n is 3, ARE USEFUL FOR THEIR CORONARY DILATING EFFECT AND ANTIHYPERTENSIVE EFFECTS. Processes for the production of these compounds are set forth below.

Inventors

  • 👤 Friedrich Bossert
  • 👤 Wulf Vater

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-27 08:15
CPC Classifications
C; C07; C07D; C07D211/00; C07D211/04; C07D211/80; C07D211/84; C07D211/90

Claims Analysis

Total Claims: 22
Claim 1
Independent Claim 156 words
A compound according to claim 1, wherein R is hydrogen, alkyl of one to six carbon atoms, alkyl of one to six carbon atoms substituted by hydroxyl, or benzyl, R'''' is alkyl of one to six carbon atoms, alkenyl of two to six carbon atoms, alkinyl of two to six carbon atoms or alkyl of one to six carbon atoms substituted by hydroxyl, R'''''' is phenyl SOnR1 unsubstituted or substituted by a member selected from the group consisting of nitro, amino, acylamino of 1 to 2 carbon atoms, hydroxyl, acyloxy of one to two carbon atoms, one or two alkyl moieties of one to four carbon atoms, one or two alkoxy moieties of one to four carbon atoms and one or two halogen atoms, n is 0, 1, 2 or 3, and R1 is alkyl of one to four carbon atoms when n is 0, 1 or 2 and R1 is hydrogen when n is 3.
Claim 2
Dependent Claim 13 words
The compound according to claim 1 which is 2,6-dimethyl-4-(2''-methylmercaptophenyl)-1,4-dihydropyridine-3,5 -dicarboxylic acid dimethyl ester.
Claim 3
Dependent Claim 13 words
The compound according to claim 1 which is 2,6-dimethyl-4-(4''-methylmercaptophenyl)-1,4-dihydropyridine-3,5 -dicarboxylic acid dimethyl ester.
Claim 4
Dependent Claim 13 words
The compound according to claim 1 which is 2,6-dimethyl-4-(2''-methylsulphinylphenyl)-1,4-dihydropyridine-3,5 -dicarboxylic acid dimethyl ester.
Claim 5
Dependent Claim 13 words
The compound according to claim 1 which is 2,6-dimethyl-4-(2''-methylsulphonylphenyl)-1,4-dihydropyridine-3,5 -dicarboxylic acid dimethyl ester.
Claim 6
Dependent Claim 13 words
The compound according to claim 1 which is 2,6-dimethyl-4-(2''-methylsulphonylphenyl)-1,4-dihydropyridine-3,5 -dicarboxylic acid diethyl ester.
Claim 7
Dependent Claim 13 words
The compound according to claim 1 which is 2,6-dimethyl-4-(4''-methylsulphonylphenyl)-1,4-dihydropyridine-3,5 -dicarboxylic acid dimethyl ester.
Claim 8
Dependent Claim 13 words
The compound according to claim 1 which is 2,6-dimethyl-4-(3''-nitro-4''-methylmercaptophenyl)-1,4-dihydropyridine-3,5 -dicarboxylic acid dimethyl ester.
Claim 9
Dependent Claim 13 words
The compound according to claim 1 which is 2,6-dimethyl-4-(3''-nitro-6''-methylmercaptophenyl)-1,4-dihydropyridine-3,5 -dicarboxylic acid dimethyl ester.
Claim 10
Dependent Claim 13 words
The compound according to claim 1 which is 2,6-dimethyl-4-(2''-methylmercaptophenyl)-1,4-dihydropyridine-3,5 -dicarboxylic acid diallyl ester.
Claim 11
Dependent Claim 13 words
The compound according to claim 1 which is 1,2,6-trimethyl-4-(4''-methylsulphonylphenyl)-1,4-dihydropyridine-3,5 -dicarboxylic acid dimethyl ester.
Claim 12
Dependent Claim 13 words
The compound according to claim 1 which is 1,2,6-trimethyl-4-(4''-methylmercaptophenyl)-1,4-dihydropyridine-3,5 -dicarboxylic acid dimethyl ester.
Claim 13
Dependent Claim 13 words
The compound according to claim 1 which is 1,2,6-trimethyl-4-(2''-methylmercaptophenyl)-1,4-dihydropyridine-3,5 -dicarboxylic acid dimethyl ester.
Claim 14
Dependent Claim 15 words
The compound according to claim 1 which is 1,2,6-trimethyl-4-(4''-methylmercaptophenyl)-1,4-dihydropyridine-3,5 -dicarboxylic acid di-( Beta -ethoxyethyl ester).
Claim 15
Dependent Claim 12 words
The compound according to claim 1 which is 1,2,6-trimethyl-4-(3''-nitro-4''-methylmercaptophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid dimethyl ester.
Claim 16
Dependent Claim 12 words
The compound according to claim 1 which is 1,2,6-trimethyl-4-(2''-mercaptophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid dipropargyl ester.
Claim 17
Dependent Claim 12 words
The compound according to claim 1 which is 2,6-dimethyl-4-(4''-sulphonyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester.
Claim 18
Dependent Claim 13 words
The compound according to claim 1 which is 2,6-dimethyl-4-(3''-nitro-6''-sulphophenyl)-1,4-dihydropyridine-3,5 -dicarboxylic acid diethyl ester.
Claim 19
Dependent Claim 13 words
The compound according to claim 1 which is 2,6-dimethyl-4-(4''-nitro-6''-sulphophenyl)-1,4-dihydropyridine-3,5 -dicarboxylic acid diethyl ester.
Claim 20
Dependent Claim 15 words
The compound according to claim 1 which is 2,6-dimethyl-4-(4''-methylmercaptophenyl)-1,4-dihydropyridine-3,5 -dicarboxylic acid di-( Beta -ethoxyethyl ester).
Claim 21
Dependent Claim 13 words
The compound according to claim 1 which is 1-benzyl-2,6-dimethyl-4-(4''-mercaptophenyl)-1,4-dihydropyridine-3,5 -dicarboxylic acid dimethyl ester.
Claim 22
Dependent Claim 15 words
The compound according to claim 1 which is 1- Beta -hydroxyethyl-2,6-dimethyl-4-(4''-methylmercaptophenyl)-1,4-dihydropyridine -3,5-dicarboxylic acid dimethyl ester.

References Cited (Backward Citations)

US3325505A Cited
US3441648A Cited
US3511847A Cited
US3485847A Cited
US3488359A Cited
US3455939A Cited
US3455945A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1975-10-03 1976-04-03 1976-10-03 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1979-10-03 1980-04-03 1980-10-03 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1983-10-03 1984-04-03 1984-10-03 $7700.00 Window Closed / Lapsed

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