Carboxylic acid derivatives, processes for the preparation...

Details Carboxylic acid derivatives, processes for the preparation... Carboxylic acid derivatives, processes for the preparation...

C - Chemistry, Metallurgy

07

C

167/179, 260/292

C07C 317/44 (2006.01) A61K 31/19 (2006.01) A61K 31/215 (2006.01) A61K 31/255 (2006.01) A61K 31/275 (2006.01) C07C 59/64 (2006.01) C07C 59/68 (2006.01) C07C 59/88 (2006.01) C07C 323/62 (2006.01)

Patent

CA 1316922

ABSTRACT New carboxylic acid derivatives, processes for the preparation thereof, the use thereof and pharma- ceutical compositions containing them The present invention provides carboxylic acid derivatives of the general formula:- Image (I) wherein R1 is an optionally substituted aryl or aryloxy radical, R2 is a hydrogen atom, a lower alkyl radical or an R1-A- radical and, when X is a cyano group, R2 can also be an acylamino or amino radical, A is a straight-chained or branched, saturated or unsaturated alkylene radical containing 3 to 8 carbon atoms which has a chain length of at least 3 carbon atoms, X is a cyano group or a radical of the general formula -B-R3 or -D-NR4R5, in which B is O, S, SO, SO2, O(CO), OSO2, NHCO, NHSO2 or CO, D is a valency bond, SO2 or CO, R3 is an alkyl, trifluoromethyl, cycloalkyl, aralkyl, aralkenyl or aryl radical, the aryl moieties of which are optionally substituted, R4 is a hydrogen atom, a lower alkyl radical or an optionally substituted aryl or aralkyl radical, R5 is a hydrogen atom or a lower alkyl radical or R4 and R5 together form an alkylene chain containing 4 to 6 carbon atoms which can be interrupted by O, S or NR6 and R6 is a hydrogen atom, a lower alkyl radical or an optionally substituted phenyl or benzyl radical, as well as the physiologic- ally acceptable salts, esters, amides and nitriles thereof, with the proviso that: a) when A is an alkylene radical with 3 carbon atoms, a1) in all cases, an aryl radical R1 is not an unsubstituted phenyl radical and a2) X is not -CN, -NHCOR3 or - NR4R5; b) when X is a methylthio radical, R2 is not a methyl radical; c) when X is -NH2 or -NHCOCH3, R1A- is not 4-phenyl- butyl or 4-(4-methoxyphenyl)-butyl; d) when X is 2,3-dinitrophenyl, R1A- is not 4-phenyl- butyl or 5-phenylpentyl; and e) when X is - COCH3, R1A- is not 3-(2-chlorophenyl)- propyl or 5-(4-methoxyphenyl)-pentyl; the compounds may be used in combatting diabetes, prediabetes, adipositas or atherosclerosis, in pharmaceutical compositions.

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