GLYCERYL 5-AROYL-PYRROLE-ACETATES AND PROPIONATES

摘要

1385652 Glyceryl - 5 - aroyl - pyrrole - acetates and propionates and pharmaceutical compositions containing them McNEIL LABORATORIES Inc 19 Jan 1973 [21 Jan 1972] 2816/73 Heading C2C The invention comprises compounds of formula wherein Gly represents -CH 2 CH(OH)CH 2 OH; Ar represents a phenyl, thienyl, 5-methylthienyl, mono-, di- or tri-substituted phenyl group, each substituent of said substituted phenyl being a halo, C 1-6 alkyl, -CF 3 , C 1-6 alkoxy, nitro, -NH 2 , -CN or -SCH 3 group; Ar represents a phenyl, mono-, di- or trisubstituted phenyl group, each substituent of said phenyl group being a halo, C 1-6 alkyl, or C 1-6 alkoxy group; R represents H or a C 1-6 alkyl group; R 1 represents a H, C 1-6 alkyl or benzyl group; and R 2 represents H or a C 1-6 alkyl group, provided that: (i) when Ar is a nitro-substituted phenyl or amino-substituted phenyl group, then, with regard to Formula (I-a), R is H and R 1 is a C 1-6 alkyl group; and with regard to Formula (I-e), said R 2 is H; (ii) when Ar is a cyanophenyl group, then R 1 is a C 1-6 alkyl group; and (iii) when R 1 is H, then R is also a hydrogen atom. These compounds may be obtained by heating a compound of formula wherein X is the residual portion of Formulµ I-a, I-b, I-c, I-d or I-e defined above which is attached to the carboxylic function, with an aqueous solution of acetic acid. The following intermediates are referred to: cyanomethyl- 1 - methyl - 5 - (p - toluoyl) - pyrrole - 2 - acetate obtained by the reaction of sodium-1-methyl-5- (p - toluoyl) - pyrrole - 2 - acetate with chloroacetonitrile, in Example I. For similar intermediates see also Example II. 2,2-Dimethyl-1,3- dioxolanylmethyl - 1 - methyl - 5 - (p - toluoyl)- pyrrole-2-acetate is obtained by treating cyanomethyl - 1 - methyl - 5 - (p - toluoyl) - pyrrole- 2-acetate with acetone ketal of glycerine in Example III. For similar intermediates see also Example IV. The invention also comprises a pharmaceutical composition which contains as an active ingredient a compound according to the invention together with a pharmaceutically acceptable inert diluent or carrier.