ANALOGIFOERFARANDE Foer FRAMSTAELLNING AV NYA TERAPEUTISKT Effektiv AMINOPYRROLDERIVAT

摘要

1427945 Derivatives of 3-aminopyrrole GRUPPO LEPETIT SpA 25 July 1974 [22 Aug 1973] 39790/73 Heading C2C The invention comprises compounds of formula and their salts with pharmaceutically acceptable acids, wherein R is hydrogen, (C 1-4 )alkyl, benzyl or halo-substituted benzyl; R 1 is hydrogen, (C 1-4 )alkyl, phenyl or phenyl carrying one to three substituents chosen from (C 1-4 )alkyl, (C 1-4 )alkoxy, benzyloxy, fluoro, chloro, bromo, hydroxy and nitro; R 2 is hydrogen, (C 1-4 )alkyl, formyl, (C 2-4 )aliphatic acyl, benzoyl, carbo- (C 1-4 )alkoxy -(C 2-4 )aliphatic acyl, carbamyl, phenylcarbamyl, thiocarbamyl, phenylthiocarbamyl, benzoylthiocarbamyl, carboxyphenyl, benzenesulphonyl, (C 1-4 )alkylsulphonyl, toluenesulphonyl or phenacylsulphonyl; R 3 is hydrogen or (C 1-4 )alkyl or R 2 and R 3 together are (C 2-4 )alkylidene, benzylidene or halo-substituted benzylidene; R 4 is (C 2-4 )- aliphatic acyl, benzoyl, benzoyl carrying one to three substituents chosen from fluoro, chloro, bromo and (C 1-4 )alkoxy, carbo(C 1-4 )alkoxy, carboxy, carbamyl, methylcarbamyl or phenylcarbamyl and R 5 is hydrogen, (C 1-4 )alkyl, carbo(C 1-4 )alkoxy, carbo (C 1-4 )alkoxy-methyl, trifluoromethyl, carboxy, carbamyl or carbazoyl or R 4 and R 5 together are -CO-(CH 2 ) n -, wherein the carbonyl group is connected to the carbon atom of the pyrrole ring which bears the substituent R 4 and n is 2, 3 or 4, provided that when R 1 =R 5 =Me and R=H, then one of R 2 , R 3 #H and R 4 #CO 2 Et. These compounds are prepared (when R=R 2 =R 3 =H) by reacting RNH-CHR 1 -CN with either R 2 COCH 2 R 4 or R 5 C # CR 4 and cyclizing the thus formed inter-- mediate of formula the products may then be reacted further if desired to convert the 3-NH 2 groups or other functional groups present to different substituent groups and/or replace the 1-H atom by R(#H). Therapeutic compositions having anti-inflammatory antipyretic and analgesic activity, C.N.S. depressant activity, and in some cases sedative and myorelaxing activity, comprise compounds of the above formula, and may be administered orally, parenterally or rectally.