← Back to Patent Explorer
US3764683A Expired / Lapsed US ⏱️ 0.0 years remaining

Composition and method for effecting coronary dilation using cyanophenyl-1,4-dihydropyridine derivatives

Assignee: Bayer AG
•
Filing: 1971-08-06
•
Granted: 1973-10-09
•
Expires: 1991-08-06
📄 Original PDF 🌐 Google Patents 🔄 Sync Now

Abstract

Abstract Cyanophenyl-1,4-dihydropyridine derivatives of the formula: WHEREIN R is hydrogen, saturated or unsaturated, straight, branched or cyclic alkyl of 1 to 6 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 1, 2 or 3 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 or 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, and R'''''' is aryl substituted by cyano or by cyano and one to nine members selected from the group consisting of cyano, 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, ARE USEFUL FOR THEIR CORONARY DILATING EFFECT AND ANTIHYPERTENSIVE EFFECTS. Processes for the production of these compounds are set forth below.

Inventors

  • 👤 F Bossert
  • 👤 W Vater

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-28 05:51
CPC Classifications
C; C07; C07D; C07D211/00; C07D211/04; C07D211/80; C07D211/84; C07D211/90

Claims Analysis

Total Claims: 29
Claim 1
Independent Claim 55 words
A pharmaceutical composition according to claim 1, wherein R is hydrogen, alkyl of one to six carbon atoms; and R'''' is straight or branched chain alkyl of one to six carbon atoms, said alkyl interrupted by one oxygen atom, furfuryl, alkenyl of two to six carbon atoms or alkinyl of two to six carbon atoms.
Claim 2
Dependent Claim 38 words
A pharmaceutical composition according to claim 1, wherein R is hydrogen, methyl or benzyl; R'' is methyl or ethyl; R'''' is methyl, ethyl, isopropyl, butyl, Beta -propoxyethyl, furfuryl, allyl or propargyl; and R'''''' is cyanophenyl, cyano-chlorophenyl or nitrocyanophenyl.
Claim 3
Dependent Claim 12 words
A pharmaceutical composition according to claim 1, containing 2,6-dimethyl-4-(4''-cyanophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid methyl ester.
Claim 4
Dependent Claim 12 words
A pharmaceutical composition according to claim 1, containing 2,6-dimethyl-4-(3''-cyanophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester.
Claim 5
Dependent Claim 13 words
A pharmaceutical composition according to claim 1, containing 2,6-dimethyl-4-(3''-cyano-4''-chlorophenyl)-1,4-dihydro-pyridine-3, 5-dicarboxylic acid dimethyl ester.
Claim 6
Dependent Claim 12 words
A pharmaceutical composition according to claim 1, containing 2,6-dimethyl-4-(3''-cyanophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diisopropyl ester.
Claim 7
Dependent Claim 12 words
A pharmaceutical composition according to claim 1, containing 2,6-dimethyl-4-(3''-cyanophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diallyl ester.
Claim 8
Dependent Claim 12 words
A pharmaceutical composition according to claim 1, containing 4-(2''-cyanophenyl)-2,6-dimethyl-1,4-dihydropyridine-dicarboxylic acid dimethyl ester.
Claim 9
Dependent Claim 12 words
A pharmaceutical composition according to claim 1, containing 4-(2''-cyanophenyl)-2,6-dimethyl-1,4-dihydropyridine-dicarboxylic acid diethyl ester.
Claim 10
Dependent Claim 12 words
A pharmaceutical composition according to claim 1, containing 1,2,6-trimethyl-4-(3''-cyanophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester.
Claim 11
Dependent Claim 12 words
A pharmaceutical composition according to claim 1, containing 1,2,6-trimethyl-4-(2''-cyanophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid dimethyl ester.
Claim 12
Dependent Claim 13 words
A pharmaceutical composition according to claim 1, containing 1,2,6-trimethyl-4-(3''-cyanophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid di-( Beta -propoxyethylester).
Claim 13
Dependent Claim 13 words
A pharmaceutical composition according to claim 1, containing 1,2,6-trimethyl-4-(3''-cyano-4''-chlorophenyl)-1,4-dihydropyridine-3,5 -dicarboxylic acid diallyl ester.
Claim 14
Dependent Claim 13 words
A pharmaceutical composition according to claim 1, containing 1-methyl-2,6-diethyl-4-(3''-cyano-4''-chlorophenyl)-1,4-dihydropyridine-3,5 -dicarboxylic acid diethyl ester.
Claim 15
Dependent Claim 12 words
A pharmaceutical composition according to claim 1, containing 1,2,6-trimethyl-4-(2''-cyanophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester.
Claim 16
Dependent Claim 12 words
A pharmaceutical composition according to claim 1, containing 1,2,6-trimethyl-4-(2''-cyanophenyl)-1,4-dihYdropyridine-3,5-dicarboxylic acid diisopropyl ester.
Claim 17
Dependent Claim 12 words
A pharmaceutical composition according to claim 1, containing 1,2,6-trimethyl-4-(2''-cyanophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diallyl ester.
Claim 18
Dependent Claim 13 words
A pharmaceutical composition according to claim 1, containing 1,2,6-trimethyl-4-(3''-nitro-4''-cyanophenyl)-1,4-di-hydropyridine-3,5 -dicarboxylic acid dimethyl ester.
Claim 19
Dependent Claim 12 words
A pharmaceutical composition according to claim 1, containing 1,2,6-trimethyl-4-(3''-cyanophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid difurfuryl ester.
Claim 20
Dependent Claim 13 words
A pharmaceutical composition according to claim 1, containing 1,2,6-trimethyl-4-(3''-cyano-4''-chlorophenyl)-1,4-di-hydropyridine-3,5 -dicarboxylic acid dipropargyl ester.
Claim 21
Dependent Claim 13 words
A pharmaceutical composition according to claim 1, containing N-benzyl-2,6-dimethyl-4-(4''-cyanophenyl)-1,4-dihydro-pyridine-3,5 -dicarboxylic acid di-n-butyl ester.
Claim 22
Independent Claim 26 words
The method of effecting coronary dilation which comprises administering to an animal in need thereof a coronary dilating effective amount of a compound of the formula:
Claim 23
Dependent Claim 37 words
The method according to claim 23, wherein R is hydrogen, methyl or benzyl; R'' is methyl or ethyl; R'''' is methyl, ethyl, isopropyl, butyl, Beta -propoxyethyl, furfuryl, allyl or propargyl; and R'''''' is cyanophenyl, cyano-chlorophenyl or nitrocyanophenyl.
Claim 24
Dependent Claim 15 words
The method according to claim 23, wherein the compound is 2, 6-dimethyl-4-(4''-cyanophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid methyl ester.
Claim 25
Dependent Claim 15 words
The method according to claim 23, wherein the compound is 2, 6-dimethyl-4-(3''-cyanophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester.
Claim 26
Dependent Claim 14 words
The method according to claim 23, wherein the compound is 4-(2''-cyanophenyl)-2,6-dimethyl-1,4-dihydropyridine-dicarboxylic acid dimethyl ester.
Claim 27
Dependent Claim 14 words
The method according to claim 23, wherein the compound is 4-(2''-cyanophenyl)-2,6-dimethyl-1,4-dihdyropyridine-dicarboxylic acid diethyl ester.
Claim 28
Dependent Claim 15 words
The method according to claim 23, wherein the compound is 1, 2,6-trimethyl-4-(2''-cyanophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester.
Claim 29
Dependent Claim 15 words
The method according to claim 23, wherein the compound is 1, 2,6-trimethyl-4-(2''-cyanophenyl)-1,4-dihdyropyri-dine-3,5-dicarboxylic acid dimethyl ester.

References Cited (Backward Citations)

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

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1976-10-08 1977-04-09 1977-10-09 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1980-10-08 1981-04-09 1981-10-09 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1984-10-08 1985-04-09 1985-10-09 $7700.00 Window Closed / Lapsed

Assigned Categories & Tags

No categories assigned to this patent yet.

Assign Category Tag