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US4559350A Expired / Lapsed US ⏱️ 0.0 years remaining

Antihypertensive tetrahydropyridine 3-cyano 5-carboxylic acid esters

Assignee: Bayer AG
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Filing: 1984-08-24
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Granted: 1985-12-17
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Expires: 2004-08-24
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Abstract

Abstract 1,2,3,4-Tetrahydropyridines of the formula ##STR1## in which R 1 is optionally substituted aryl or heterocyclic, R 2 is an organic radical, X is a nitrile or an ester R 3 and R 5 are identical or different and each represent hydrogen, a straight-chain or branched or salts thereof with physiologically tolerated acids are antihypertensives.

Inventors

  • 👤 Egbert Wehinger
  • 👤 Stanislav Kazda
  • 👤 Andreas Knorr

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-09 18:58
CPC Classifications
C; C07; C07D; C07D211/00; C07D211/04; C07D211/68; C07D211/72; C07D211/78; A; A61; A61P; A61P1/00; A61P11/00; A61P13/00; A61P13/02; A61P15/00; A61P25/00; A61P25/28; A61P9/00; A61P9/08; A61P9/10; A61P9/12

Claims Analysis

Total Claims: 11
Claim 1
Independent Claim 260 words
A 1,2,3,4-tetrahydropyridine of the formula ##STR31## in which R 1 represents phenyl or naphthyl optionally substituted by 1 or 2 identical or different substituents from the group consisting of phenyl, straight-chain or branched alkyl having 1 to 8 carbon atoms, cycloalkyl having 3 to 7 carbon atoms, alkoxy having 1 to 4 carbon atoms, tri-tetra- and pentamethylene, dioxamethylene, halogen, trifluoromethyl, trifluoro-methoxy, difluoromethoxy, tetrafluoroethoxy or cyano, R 2 represents a straight-chain, branched or cyclic, saturated or unsaturated hydrocarbon radical having up to 20 carbon atoms, which is optionally interrupted by one oxygen or sulphur atom in the chain and/or which is optionally substituted by halogen, cyano, hydroxyl, α-, β- or γ-pyridyl, phenyl, phenoxy or phenylthio, it being possible for the phenyl groups to be substituted by halogen, cyano, dialkylamino having 1 to 4 carbon atoms in each alkyl radical, alkoxy having 1 to 4 carbon atoms, alkyl having 1 to 4 carbon atoms, trifluoromethyl or trifluoromethoxy, or by an amino group which in turn is substituted by two identical or different substituents from the group consisting of alkyl having 1 to 4 carbon atoms, phenyl or benzyl, R 3 and R 5 , which are identical or different, each represent hydrogen, a straight-chain or branched alkyl radical having up to 4 carbon atoms, a phenyl radical or a benzyl radical, and R 4 represents hydrogen, a straight-chain or branched alkyl radical having up to 4 carbon atoms which is optionally interrupted by an oxygen atom, a phenyl radical or a benzyl radical, or a salt thereof with a physiologically tolerated acid.
Claim 2
Dependent Claim 260 words
A 1,2,3,4-tetrahydropyridine of the formula ##STR31## in which R 1 represents phenyl or naphthyl optionally substituted by 1 or 2 identical or different substituents from the group consisting of phenyl, straight-chain or branched alkyl having 1 to 8 carbon atoms, cycloalkyl having 3 to 7 carbon atoms, alkoxy having 1 to 4 carbon atoms, tri-tetra- and pentamethylene, dioxamethylene, halogen, trifluoromethyl, trifluoro-methoxy, difluoromethoxy, tetrafluoroethoxy or cyano, R 2 represents a straight-chain, branched or cyclic, saturated or unsaturated hydrocarbon radical having up to 20 carbon atoms, which is optionally interrupted by one oxygen or sulphur atom in the chain and/or which is optionally substituted by halogen, cyano, hydroxyl, α-, β- or γ-pyridyl, phenyl, phenoxy or phenylthio, it being possible for the phenyl groups to be substituted by halogen, cyano, dialkylamino having 1 to 4 carbon atoms in each alkyl radical, alkoxy having 1 to 4 carbon atoms, alkyl having 1 to 4 carbon atoms, trifluoromethyl or trifluoromethoxy, or by an amino group which in turn is substituted by two identical or different substituents from the group consisting of alkyl having 1 to 4 carbon atoms, phenyl or benzyl, R 3 and R 5 , which are identical or different, each represent hydrogen, a straight-chain or branched alkyl radical having up to 4 carbon atoms, a phenyl radical or a benzyl radical, and R 4 represents hydrogen, a straight-chain or branched alkyl radical having up to 4 carbon atoms which is optionally interrupted by an oxygen atom, a phenyl radical or a benzyl radical, or a salt thereof with a physiologically tolerated acid.
Claim 3
Dependent Claim 153 words
A compound or salt according to claim 1, in which R 1 represents phenyl optionally substituted by one or two identical or different substituents from the group consisting of fluorine, chlorine, cyano, trifluoromethyl, trifluoromethoxy, alkyl having 1 to 4 C atoms, alkoxy having 1 to 2 C atoms, tetramethylene or phenyl, R 2 represents a straight-chain or branched cyclic alkyl or alkenyl radical having up to 12 carbon atoms which is optionally interrupted by an oxygen atom in the chain and/or which is optionally substituted by fluorine, chlorine, cyano, hydroxyl, phenyl, phenoxy or an amino group which in turn is substituted by two identical or different substituents from the group consisting of alkyl having 1 to 4 C atoms or benzyl, R 3 and R 5 are identical or different and each represent alkyl having 1 to 2 atoms, and R 4 represents hydrogen, alkyl having 1 to 4 C atoms or benzyl.
Claim 4
Dependent Claim 47 words
A compound or salt according to claim 1, in which R 1 denotes phenyl, chlorophenyl, tolyl, trifluoromethylphenyl, methoxyphenyl, cyanophenyl, trifluoromethoxyphenyl, dichlorophenyl or chlorofluorophenyl, R 2 denotes methyl, ethyl, allyl, t-butyl, methoxyethyl, benzyl, benzyloxyethyl or cyanoethyl, R 3 and R 5 denote methyl, and R 4 denotes hydrogen.
Claim 5
Dependent Claim 25 words
A compound according to claim 1, wherein such compound is methyl 3-cyano-2,6-dimethyl-4-(2-trifluoromethylphenyl)-1,2,3,4-tetrahydropyridine-5-carboxylate of the formula ##STR32## or a salt thereof with a physiologically tolerated acid.
Claim 6
Dependent Claim 25 words
A compound according to claim 1, wherein such compound is ethyl 3-cyano-2,6-dimethyl-4-(2-chlorophenyl)-1,2,3,4-tetrahydropyridine-5-carboxylate of the formula ##STR33## or a salt thereof with a physiologically tolerated acid.
Claim 7
Dependent Claim 25 words
A compound according to claim 1, wherein such compound is methyl 3-cyano-2,6-dimethyl-4-(2,3-dichlorophenyl)-1,2,3,4-tetrahydropyridine-5-carboxylate of the formula ##STR34## or a salt thereof with a physiologically tolerated acid.
Claim 8
Dependent Claim 25 words
An antihypertensive composition which consists of an amount of a compound of claim 1 effective in the treatment of hypertension, and a pharmaceutically acceptable carrier.
Claim 9
Dependent Claim 19 words
A composition according to claim 7, in the form of a tablet, capsule or pill containing a unit dose.
Claim 10
Dependent Claim 27 words
The method of combating hypertension in a patient which comprises administering to such patient an antihypertensive effective amount of a compound or salt according to claim 1.
Claim 11
Dependent Claim 26 words
The method according to claim 9, wherein such compound is methyl 3-cyano-2,6-dimethyl-4-(2-trifluoromethylphenyl)-1,2,3,4-tetrahydropyridine-5-carboxylate, ethyl 3-cyano-2,6-dimethyl-4-(2-chlorophenyl)-1,2,3,4-tetrahydropyridine-5-carboxylate, or methyl 3-cyano-2,6-dimethyl-4-(2,3-dichlorophenyl)-1,2,3,4-tetrahydropyridine-5-carboxylate, or a salt thereof with a physiologically tolerated acid.

References Cited (Backward Citations)

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USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1988-12-16 1989-06-17 1989-12-17 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1992-12-16 1993-06-17 1993-12-17 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1996-12-16 1997-06-17 1997-12-17 $7700.00 Window Closed / Lapsed

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