Patent CA-2085201-C (CA)
Inventor: SOYKA RAINER
IPC: A61P11/00
Filed: 1992-12-11
Granted: 2004-07-06
Abstract: This invention relates to pyridyl derivatives of formula I      wherein n represents the number 2, 3, 4 or 5; A denotes a carbon-nitrogen bond or a straight-chained C1-4-alkylene group optionally substituted by one or two alkyl groups; X denotes a nitromethylene group, a cyanomethylene group optionally substituted by an R9 group, or a group of the formula =N-R10, wherein R9 denotes a cyano group, an aminocarbonyl group, a dialkyl amino carbonyl group, -CO-OR', -CO-O-(HCR")-O-CO-R''' or -CO-O-(HCR")-O-CO-OR''' wherein R' denotes a straight-chained or branched C1-6 alkyl group, a C5-7 cycloalkyl group, benzyl, 1-phenylethyl, 2-phenylethyl, 3-phenylpropyl, methoxymethyl, or a cinnamyl group, R" denotes hydrogen or methyl, and R''' denotes a straight-chained or branched C1-6 alkyl group, a C5-7 cycloalkyl group, phenyl, benzyl, 1-phenylethyl, 2-phenylethyl, or 3-phenylpropyl, R10 denotes a cyano, alkanesulphonyl, phenylsulphonyl, phenylalkanesulphonyl, amino sulphonyl, alkylaminosulphonyl, dialkylaminosulphonyl, phenylcarbonyl, aminocarbonyl, alkylaminocarbonyl or dialkylaminocarbonyl group; Y denotes an alkoxy, phenoxy, alkylthio or phenylthio group or a group of the formula -R1NR2, wherein R1 denotes a hydrogen atom; a straight-chained or branched C1-10-alkyl; group, unsubstituted or substituted in the 2-, 3- or 4-position by a hydroxy, amino, alkylamino or dialkylamino group; a C1-4-alkyl group substituted by a phenyl or pyridyl group and optionally additionally substituted in the 2-, 3-, or 4-position by a hydroxy group; a C3-4-cycloalkyl group; a C5-8-cycloalkyl group in which an ethylene bridge is optionally replaced by an o-phenylene group, a C6-8-bicycloalkyl group optionally substituted by 1, 2 or 3 alkyl groups, or an exonobornyl adamantyl, alkoxy or trimethylsilylalkyl group, and R2 denotes a hydrogen atom or a straight-chained alkyl group or R1 and R2 together with the nitrogen atom between them denote a cyclic C4-6-alkyleneimino group optionally substituted by one or two alkyl groups or by a phenyl group; R3 denotes a hydrogen atom or a C1-3-alkyl group; R4 and R5 each denote a hydrogen atom or together represent a carbon-carbon bond; R6 denotes a pyridyl group optionally substituted in the 3- or 4-position by an alkyl group; R7 denotes a cyano, tetrazolyl, carboxy aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl group, a group of formula -CO-OR', -CO-O-(HCR")-O-CO-R''' or -CO-O-(HCR")-O-CO-OR''' wherein R' denotes a straight-chained or branched C1-6 alkyl group, a C5-7 cycloalkyl group, benzyl, 1-phenylethyl, 2-phenylethyl, 3-phenylpropyl, methoxymethyl, or a cinnamyl group, R" denotes hydrogen or methyl, and R''' denotes a straight-chained or branched C1-6 alkyl group, a C5-7 cycloalkyl group, phenyl, benzyl, 1-phenylethyl, 2-phenylethyl, or 3-phenylpropyl, R7 or R9 is optionally carboxy when Y is R1NR2-; R8 denotes a hydrogen, fluorine, chlorine, bromine or iodine atom or an alkyl, alkoxy or trifluoromethyl group; whilst unless otherwise specified any alkyl or alkoxy moiety contains one to three carbon atoms, and unless otherwise specified any phenyl nuclei are optionally mono- or disubstituted by fluorine, chlorine or bromine atoms or by alkyl, hydroxy, alkoxy, phenyl, nitro, amino, alkylamino, dialkylamino, alkanoylamino, cyano, carboxy, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, trifluoromethyl, alkanoyl, aminosulphonyl, alkylaminosulphonyl or dialkylamino-sulphonyl groups, wherein the substituents are identical or different; or an enantiomer thereof, a cis- or trans-isomer thereof, where R4 and R5 together denote a carbon-carbon bond, or a salt thereof. The new compounds have valuable pharmacological properties, in particular, antithrombotic effects.