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US3943140A Expired / Lapsed US ⏱️ 0.0 years remaining

2,3,5,6-Tetracarboxy-1,4-dihydropyridine derivatives

Assignee: Bayer AG
•
Filing: 1974-11-15
•
Granted: 1976-03-09
•
Expires: 1994-11-15
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Abstract

Abstract 1,4-Dihydropyridines bearing carboxy functions in the 3-, 5- and 6- or 2-, 3-, 5- and 6-positions and being substituted in the 4-position by phenyl, substituted phenyl, naphthyl, phenylalkyl or a heterocyclic group are antihypertensive agents and coronary vessel dilators. The compounds, of which 2-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5,6-tricarboxylic acid triethylester is a representative embodiment, are prepared through condensation of an enamine with an ylidene acid ester, the latter being separately prepared or prepared in situ.

Inventors

  • 👤 Friedrich Bossert
  • 👤 Horst Meyer
  • 👤 Wulf Vater

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-07 20:33
CPC Classifications
C; C07; C07D; C07D401/00; C07D401/02; C07D401/04; C07D211/00; C07D211/04; C07D211/80; C07D211/84; C07D211/90

Claims Analysis

Total Claims: 11
Claim 1
Independent Claim 230 words
A compound of the formula: ##SPC52## or a pharmaceutically acceptable nontoxic salt thereof, wherein R is hydrogen, alkyl of up to 4 carbon atoms or alkenyl of up to 4 carbon atoms; R 2 is alkyl of up to 6 carbon atoms, alkenyl of up to 6 carbon atoms, said alkyl substituted by hydroxyl, said alkenyl substituted by hydroxyl, said alkyl interrupted by oxygen or said alkenyl interrupted by oxygen; R 3 is alkyl of up to 6 carbon atoms or alkenyl of up to 6 carbon atoms; R 5 is hydrogen or alkyl of 1 to 4 carbon atoms; n is 0, 1, 2 or 3; and X is phenyl; phenyl substituted by one or two nitro groups; one cyano group; one azido group; one or two trifluoromethyl groups; one S(O) n alkyl wherein n is 0 or 2 and alkyl is of 1 to 4 carbon atoms; one or two alkyl groups of 1 to 4 carbon atoms; one, two or three alkoxy groups of 1 to 4 carbon atoms; one or two acetoxy groups; one or two amino groups; one or two acetylamino groups; one or two alkylamino groups of 1 to 4 carbon atoms; one or two dialkylamino groups of 1 to 4 carbon atoms in each alkyl group; one to three chlorine, bromine or fluorine atoms, or by one phenyl moiety; naphthyl; benzyl; or phenethyl.
Claim 2
Dependent Claim 230 words
A compound of the formula: ##SPC52## or a pharmaceutically acceptable nontoxic salt thereof, wherein R is hydrogen, alkyl of up to 4 carbon atoms or alkenyl of up to 4 carbon atoms; R 2 is alkyl of up to 6 carbon atoms, alkenyl of up to 6 carbon atoms, said alkyl substituted by hydroxyl, said alkenyl substituted by hydroxyl, said alkyl interrupted by oxygen or said alkenyl interrupted by oxygen; R 3 is alkyl of up to 6 carbon atoms or alkenyl of up to 6 carbon atoms; R 5 is hydrogen or alkyl of 1 to 4 carbon atoms; n is 0, 1, 2 or 3; and X is phenyl; phenyl substituted by one or two nitro groups; one cyano group; one azido group; one or two trifluoromethyl groups; one S(O) n alkyl wherein n is 0 or 2 and alkyl is of 1 to 4 carbon atoms; one or two alkyl groups of 1 to 4 carbon atoms; one, two or three alkoxy groups of 1 to 4 carbon atoms; one or two acetoxy groups; one or two amino groups; one or two acetylamino groups; one or two alkylamino groups of 1 to 4 carbon atoms; one or two dialkylamino groups of 1 to 4 carbon atoms in each alkyl group; one to three chlorine, bromine or fluorine atoms, or by one phenyl moiety; naphthyl; benzyl; or phenethyl.
Claim 3
Dependent Claim 106 words
A compound according to claim 1 wherein R is hydrogen or alkyl of up to 4 carbon atoms; R 2 is alkyl of up to 6 carbon atoms, hydroxyalkyl of up to 6 carbon atoms, or alkyl of up to 6 carbon atoms interrupted by oxygen; R 3 is alkyl of up to 6 carbon atoms; and X is phenyl; phenyl substituted by nitro, cyano, azido, one or two trifluoromethyl groups, alkylthio of 1 to 4 carbon atoms, one to three alkoxy groups of 1 to 4 carbon atoms, chlorine, bromine, fluorine, phenyl, nitro and chlorine, nitro and trifluoromethyl or methoxy and fluorine; naphthyl; or phenethyl.
Claim 4
Dependent Claim 71 words
A compound according to claim 1 wherein R is hydrogen or methyl; R 2 is alkyl of 1 to 4 carbon atoms or ethoxyethyl; R 3 is alkyl of 1 to 4 carbon atoms; n is 0 or 1; and X is phenyl or phenyl substituted by nitro, cyano, trifluoromethyl, di-trifluoromethyl, methoxy, trimethoxy, chlorine, fluorine, methylthio, phenyl, azido, methoxy and fluorine, nitro and chlorine, or nitro and trifluoromethyl; naphthyl; or phenethyl.
Claim 5
Dependent Claim 12 words
The compound according to claim 1 which is 4-(2'-trifluoromethylphenyl-1,4-dihydropyridine-2,3,5,6-tetracarboxylic acid ethyl ester.
Claim 6
Dependent Claim 12 words
The compound according to claim 1 which is 4-(3'-methoxyphenyl)-1,4-dihydropyridine-2,3,5,6-tetracarboxylic acid tetraethyl ester.
Claim 7
Dependent Claim 13 words
The compound according to claim 1 which is 4-(3'-methoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester-2,6-dicarboxylic acid.
Claim 8
Dependent Claim 12 words
The compound according to claim 1 which is 4-(3'-chlorophenyl)-1,4-dihydropyridine-2,3,5,6-tetracarboxylic acid tetraethyl ester.
Claim 9
Dependent Claim 15 words
The compound according to claim 1 which is 4-(3'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid dimethyl ester-1,6-diacetic acid dimethyl ester.
Claim 10
Dependent Claim 12 words
The compound according to claim 1 which is 4-(2'-nitrophenyl)-1,4-dihydropyridine-2,3,5,y-tetracarboxylic acid tetraethyl ester.
Claim 11
Dependent Claim 13 words
The compound according to claim 1 which is 4-(3'-chlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester-2,6-dicarboxylic acid.

References Cited (Backward Citations)

US3862161A Cited
US3855231A Cited
US3860601A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1979-03-09 1979-09-08 1980-03-09 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1983-03-09 1983-09-08 1984-03-09 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1987-03-09 1987-09-08 1988-03-09 $7700.00 Window Closed / Lapsed

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