GB550011A - Improvements in or relating to the production of therapeutically effective derivatives of 4:4-diamino diphenyl sulphone - Google Patents

Abstract

550,011. Sulphones. LILLY & CO., E., KHARASCH, M. S., and REINMUTH, O. Nov. 6, 1940, No. 16183. [Class 2 (iii)] Therapeutically useful compounds are prepared by reacting 4 : 4<SP>1</SP>-diaminodiphenylsulphone with formaldehyde and an N - acylcysteine. The two latter reactants are employed in such quantities that substitution takes place at either one or both of the amino groups in the sulphone. The sulphone may first be reacted with formaldehyde and the resulting condensation product then treated with one or two equivalents of the acylcysteine. The acyl group may be derived from the alkanoic and haloalkanoic acids of less than eight carbon atoms, aromatic and heterocyclic carboxylic acids and aromatic sulphonic acids, e.g. formyl, acetyl, chloracetyl, bromopropionyl, benzoyl, nicotinyl and benzenesulphonyl. The products may be converted into their salts with alkali and alkaline earth metals, ammonia, alkylamines, alkanolamines and polymethylenediamines. Examples are given of the treatment of (1) 4 : 4<SP>1</SP> - diaminodiphenylsulphone with formaldehyde and N - acetyl -, N - # - bromopropionyl-, N - benzoyl-, N-nicotinyl-, N- formyl- or N-chloracetylcysteine, the amount of formaldehyde and mercapto acid being sufficient to combine with one or both the sulphone amino groups and the products converted into their sodium salts ; (2) N : N<SP>1</SP> - dimethylene - 4 : 41- diaminodiphenylsulphone, prepared by reacting the diaminosulphone and formaldehyde, with one or two equivalents of N-acetylcysteine.