Patent ES-8604147-A1 (ES)
Title: New 1,4-dihydropyridine esters and preparation methods thereof and drugs containing said esters.
IPC: C07D409/04
Filed: 1985-05-30
Abstract: Cpds. of formula (I) and their salts are new. In (I) R is H, opt. unsatd. hydrocarbyl or morpholino-alkyl. R2 and R3 are H or linear alkyl, n is 0-3 and X is aryl (opt. substd.) benzyl, styryl, cycloalkyl, cycloalkenyl, or is naphthyl, quinolyl, isoquinolyl, pyridyl, pyrimidyl, diphenyl, furyl, pyrryl or thienyl (opt. substd.). R1 is opt. unsatd. hydrocarbyl opt. interrupted by 1 or 2 O or S and opt. substd. by 1 or 2 hydroxy it may also be -CHR4.(CH2)nY. Y is (1) N-substd. amide of nicotinic, salicyclic or 4-hydroxybenzoic acid, or (2) OOCR6 or OR6, (3) 2-tetrahydrofuryl or (4) N-(4-benzoylpiperidinyl), R5 is alkyl, acyl or arylsulphonyl. R6 is (un)satd. hydrocarbyl, or heterocyclyl or aryl opt. (I) are useful as coronary and anti-atheromatic agents, e.g. for admin. at oral doses of 5-500 mg. They are much more active and less toxic than known cpds. of similar structure. EPAB- EP-126094 B 1,4-Dihydropyridine esters and salts thereof, characterised in that they have the formula in which R is hydrogen atom or a linear or branched C1 to C4 alkyl radical R2 and R3 are each a hydrogen atom or a C1 to C4 alkyl radical R4 is a hydrogen atom or a linear C1 or C2 alkyl radical n is a number equal to 0, 1 2 or 3 X is phenyl radical which may or may not carry one to three nitro, C1 to C4 alkyl, C1 to C3 alkoxy or halogen substituents R1 is a linear or branched C1 to C4 alkyl or C2 to C4 alkenyl radical a gp of the formula -W-0-Z or -W-S-Z in which W is a linear or branched C1 to C3 alkylene gp and Z is a linear or branched c1 to C4 alkyl radical an alicyclic gp contg 5 to 6 carbon atoms which is unsubstituted or substituted by one or more methyl gps or a gp of the formula (II) with the exception of the case where Y is the 2-tetrahydrofurfuryl radical and Y is the radical derived from the N-substituted amides of nicotinic, salicyclic and 4-hydroxybenzoic acids or from the N-substituted monoacylated or sulphonylated piperazines of the formula (III) in which R5 is an acyl radical selected from acetyl, 2-furoyl, 2-thiphenecarbonyl and cinnamoyl gps or a benzenesulphonyl radical which is unsubstituted or substituted by one or more C1 to C2 alkyl radicals, one or more C1 or C2 alkoxy radicals, one or more trifluoromethyl radicals, one or more halogen atomes or an acetylamine radical a gp of the formula -0C0-R6 or -0R6 in which R6 is an acetylaminophenyl radical or a 2-tetrahydrofurfuryl or N-(4-benzoylpiperidinyl) gp. - EP-126094 B 1,4-Dihydropyridine esters and salts thereof, characterised in that they have the formula in which R is hydrogen atom or a linear or branched C1 to C4 alkyl radical R2 and R3 are each a hydrogen atom or a C1 to C4 alkyl radical R4 is a hydrogen atom or a linear C1 or C2 alkyl radical n is a number equal to 0, 1 2 or 3 X is phenyl radical which may or may not carry one to three nitro, C1 to C4 alkyl, C1 to C3 alkoxy or halogen substituents R1 is a linear or branched C1 to C4 alkyl or C2 to C4 alkenyl radical a gp of the formula -W-0-Z or -W-S-Z in which W is a linear or branched C1 to C3 alkylene gp and Z is a linear or branched c1 to C4 alkyl radical an alicyclic gp contg 5 to 6 carbon atoms which is unsubstituted or substituted by one or more methyl gps or a gp of the formula (II) with the exception of the case where Y is the 2-tetrahydrofurfuryl radical and Y is the radical derived from the N-substituted amides of nicotinic, salicyclic and 4-hydroxybenzoic acids or from the N-substituted monoacylated or sulphonylated piperazines of the formula (III) in which R5 is an acyl radical selected from acetyl, 2-furoyl, 2-thiphenecarbonyl and cinnamoyl gps or a benzenesulphonyl radical which is unsubstituted or substituted by one or more C1 to C2 alkyl radicals, one or more C1 or C2 alkoxy radicals, one or more trifluoromethyl radicals, one or more halogen atomes or an acetylamine radical a gp of the formula -0C0-R6 or -0R6 in which R6 is an acetylaminophenyl radical or a 2-tetrahydrofurfuryl or N-(4-benzoylpiperidinyl) gp. (41pp) USAB- US4656181 A Esters of 1,4-dihydroxypyridines of formula (I) and salts are new. In (I), R is H, satd. or unsatd. hydrocarbon R2, R3 and R4 are each H or straight chain alkyl n is 0, 1, 2 or 3 X is Ph opt. substd. 1-3, NO2, CN, azido, alkoxy, alkyl, OH, alkanoyloxy, carbalkoxy, NH2, alkanoylamino, alkylamino, S(O)m-alkyl with m, 0, 1 or 2, CF3 or halo R1 is satd. or unsatd. chain or cyclic hydrocarbon opt. interrupted 1 or 2, O or S, opt. substd. 1 or 2 OH or R1 is -CH-(CH2)nY Y is -OOC-R6 or -R-R6, R6 is alkanoylaminophenyl or tetrahydrofuryl. - Esp. cpds. include 2-(4-acetylaminophenoxy)-ethyl-2,6- dimethyl 5-methoxycarbonyl-4-(3-nitrophenyl) -1,4-dihydropyridine-3 carboxylate.