GB1385620A - Carbazoles - Google Patents

Abstract

1385620 Carbazoles F HOFFMANN-LA ROCHE & CO AG 23 July 1973 [24 July 1972] 34968/73 Heading C2C The invention comprises compounds of the formula wherein R represents a hydrogen or halogen atom or a hydroxy, cyano, lower alkyl, hydroxy-(lower alkyl), lower alkoxy, acyl, benzyloxy, lower alkylthio, trifluoromethyl, carboxy, carbo-(lower alkoxy), nitro, amino, mono- (lower alkyl)amino, di(lower alkyl)amino, sulphamoyl, di(lower alkyl)sulphamoyl or difluoromethylsulphonyl group and R 1 represents a halogen atom or a hydroxy, cyano, lower alkyl, hydroxy-(lower alkyl), lower alkoxy, acyl, acylamido, benzyloxy, lower alkylthio, trifluoromethyl, carboxy, carbo-(lower alkoxy), nitro, amino, mono(lower alkyl)amino, di- (lower alkyl)amino, sulphamoyl, di(lower alkyl) - sulphamoyl or difluoromethylsulphonyl group or R and R 1 together represent a lower alkylenedioxy group, R 2 represents the grouping in which A represents a cyano, hydroxy, lower alkoxy, amino(lower alkoxy), mono(lower alkyl)- amino-(lower alkoxy), di(lower alkyl)amino- (lower alkoxy) group or the grouping wherein B represents a hydroxy, carboxy, lower alkoxy, amino, hydroxyamino, mono(lower alkyl)amino, di(lower alkyl)amino, amino-(lower alkoxy), mono(lower alkyl)amino-(lower alkoxy), di(lower alkyl)amino - (lower alkoxy) group, Y and X each represent a hydrogen atom or a lower alkyl group and n stands for 1 to 7, and R 3 represents a hydrogen atom or a lower alkyl, acyl, halo-substituted acyl, carboxy- (lower alkyl), (lower alkoxycarbonyl)-(lower alkyl), aralkyl or haloaralkyl group, or R 1 represents a hydrogen atom when R, X and R 3 each represent a hydrogen atom, Y represents a lower alkyl group and B represents a hydroxy or lower alkoxy group, and, when R or R 1 represents a carboxy and/or when B represents a hydroxy or carboxy group, salts thereof with bases and, when R or R 1 represents an amino or mono (lower alkyl)amino or di(lower alkyl)amino group and/or when B or A represents an amino- (lower alkoxy) or mono(lower alkyl)amino- (lower alkoxy) or di(lower alkyl)amino-(lower alkoxy) group, addition salts thereof with acids. The term lower alkyl means an alkyl group of 1-7 carbon atoms, acyl means alkanoyl derived from a carboxylic acid containing 1-7 carbon atoms and aryl means phenyl optionally substituted by halogen, trifluoromethyl, lower alkyl, lower alkoxy, nitro, amino, lower alkylamino and di(lower alkyl)amino. The compounds may be prepared by reacting a compound of the formula with an aromatizing agent, for the manufacture of an ester of Formula I in which R or R 1 represents a carbo-(lower alkoxy) group or B represents a lower alkoxy group esterifying an acid of Formula I in which R or R 1 represents a carboxy group or B represents a hydroxy group, for the manufacture of an acid of Formula I in which R or R 1 represents a carboxy group, R 3 represents a carboxy-(lower alkyl) group or B represents a hydroxy group hydrolysing an ester of Formula I in which R or R 1 represents a carbo-(lower alkoxy) group, R 3 represents a (lower alkoxycarbonyl)-(lower alkyl) group or B represents a lower alkoxy group, for the manufacture of a compound of Formula I in which R 1 represents an amino group reacting a compound of Formula I in which R 1 represents an acylamido group with an inorganic acid, if desired replacing a hydrogen atom denoted by R 3 in a compound of Formula I by an acyl or (lower alkoxycarbonyl)-(lower alkyl) group, for the manufacture of a compound of Formula I in which R or R 1 represents a di(lower alkyl)amino group alkylating a compound of Formula I in which R or R 1 represents an amino group, for the manufacture of a compound of Formula I in which R, R 1 or A represents a hydroxy group hydrolysing an ether of Formula I in which R, R 1 or A represents a lower alkoxy group, if desired converting a compound of Formula I in which A represents a hydroxy group into a compound of Formula I in which A represents a lower alkoxy, amino-(lower alkoxy), mono(lower alkyl)amino- (lower alkoxy) or di(lower alkyl)amino-(lower alkoxy) group, for the manufacture of an alcohol of Formula I in which A represents a hydroxy group reducing an ester of Formula I in which B represents a lower alkoxy group, if desired converting a hydroxy group denoted by B in an acid of Formula I or in a salt of such an acid with a base into an amino-(lower alkoxy), mono(lower alkyl)amino-(lower alkoxy) or di- (lower alkyl)amino-(lower alkoxy) group, for the manufacture of an optically active isomer of a compound of Formula I resolving a racemate of Formula I into its optically active isomers and isolating the desired isomer and for the manufacture of a salt of a compound of Formula I in which R or R 1 represents a carboxy group and/or B represents a hydroxy or carboxy group or in which R or R 1 represents an amino, mono(lower alkyl)amino or di(lower alkyl)amino group and/or B or A represents an amino-(lower alkoxy), mono(lower alkyl)amino- (lower alkoxy) or di(lower alkyl)amino-(lower alkoxy) group reacting such a compound of Formula I with a base or an acid. The compounds may be used as anti-inflammatory, analgesic and anti-rheumatic agents.