US 4,636,505 A · Amide derivatives

Abstract

Acylanilides of the formula ##STR1## wherein R.sup.1 and R.sup.2, the same or different, each is cyano, carbamoyl, nitro, halogeno, perfluoroalkyl or other defined substituents; R.sup.3 is hydrogen or halogen; R.sup.4 is hydrogen or alkyl, or is joined to R.sup.5 ; R.sup.5 is hydrogen, hydroxy, alkoxy or acyloxy or is joined to R.sup.4 ; R.sup.6 is alkyl or halogenoalkyl, or has the formula --A.sup.3 --R.sup.8 or --A.sup.4 --X.sup.2 --A.sup.5 --R.sup.9 ; A.sup.1 and A.sup.4, the same or different, each is alkylene; A.sup.2, A.sup.3 and A.sup.5, the same or different, each is a direct link or alkylene; X.sup.1 and X.sup.2, the same or different, each is oxygen, sulphur, sulphinyl, sulphonyl, imino or alkylimino; R.sup.7 and R.sup.9, the same or different, each is alkyl, alkenyl, hydroxyalkyl, cycloalkyl, phenyl optionally substituted, naphthyl or heterocyclic optionally substituted; and R.sup.8 is phenyl, naphthyl or heterocyclic as defined above for R.sup.7 or R.sup.9 ; processes for their manufacture and pharmaceutical compositions containing them. The acylanilides possess antiandrogenic activity.

Claims9

Dependent claims

An acylanilide of the formula:

##STR17## wherein R.sup.1 is cyano, nitro, fluoro, chloro, bromo or iodo, or alkyl, alkoxy, alkanoyl, alkylthio, alkylsulphinyl, alkylsulphonyl or perfluoroalkyl each of up to 4 carbon atoms;
wherein R.sup.2 is cyano, nitro, fluoro, chloro, bromo or iodo, or alkanoyl, alkylthio, alkylsulphinyl, alkysulphonyl or perfluoroalkyl, each of up to 4 carbon atoms;
wherein R.sup.3 is hydrogen or halogen;
wherein R.sup.4 is hydrogen or alkyl or up to 4 carbon atoms;
wherein R.sup.5 is hydroxy or alkoxy or acyloxy each of up to 15 carbon atoms;
wherein R.sup.6 is alkyl or halogenoalkyl of up to 4 carbon atoms;
wherein A.sup.1 is alkylene of up to 6 carbon atoms;
wherein A.sup.2 is a direct link or alkylene of up to 6 carbon atoms;
wherein X.sup.1 is sulphur, sulphinyl or sulphonyl (--SO.sub.2 --);
wherein R.sup.7 is alkyl, alkenyl, hydroxyalkyl or cycloalkyl each of up to 6 carbon atoms, or R.sup.7 is phenyl which bears one or two substituents selected from hydrogen, halogen, nitro, and cyano, and alkyl, alkoxy, alkanoyl, alkylthio, alkylsulphinyl, alkylsulphonyl and perfluoroalkyl;
or R.sup.7 is naphthyl;
or R.sup.7 is 5- or 6-membered saturated or unsaturated heterocyclic which contains one, two or three heteroatoms selected from oxygen, nitrogen and sulphur, which heterocyclic may be a single ring or may be fused to a benzo-ring, and which heterocyclic is unsubstituted or bears one or two halogen or alkyl of up to 4 carbon atoms substituents.

9 more elements

Dependencies are inferred from the claim text.

Amide derivatives

Life of this patent

Amide derivatives

Life of this patent

Abstract

Claims9