The present invention relates to an antiandrogen compound and a method of treating prostate cancer in a patient utilizing the compound. The present invention also relates to a pharmaceutical composition which includes the compound.

A compound of the formula ##STR1## wherein X has the formula --CR.sup.5 .dbd.CR.sup.6 --, --C.tbd.C-- or ##STR2## wherein ring A is phenyl, naphthyl or heterocyclic; wherein R.sup.1 is hydrogen, alkyl, alkanoyl or aroyl; wherein R.sup.2, R.sup.3 and R.sup.4, which may be the same or different, each is an electron withdrawing substituent or each is hydrogen or alkyl, alkoxy or dialkylamino, provided that when ring A is phenyl or naphthyl at least one of R.sup.2, R.sup.3 and R.sup.4 is an electron-withdrawing substituent; wherein R.sup.5 and R.sup.6, each is hydrogen, halogeno or alkyl wherein R.sup.7 is alkyl or halogenoalkyl; and wherein R.sup.8 has the formula --Y--Q--R.sup.9 wherein Y is straight- or branched-chain alkylene or alkenylene; wherein Q is --O--, --S--, --SO-- or --SO.sub.2 --; and wherein R.sup.9 is alkyl of up to 6 carbon atoms which contains one or more defined substituents, processes for their manufacture and pharmaceutical compositions containing them. The compounds possess antiandrogenic activity and may be used in the treatment of androgen-dependent disease conditions such as prostatic disease, acne, hirsutism or seborrhoea.

The present invention relates to a nonsteroidal agonist compound having the formula: ##STR1## where R.sub.1, R.sub.2, and R.sub.3 are the same or different and are a hydrogen, a nitro, a cyano, a carbamoyl, a halogen, a perfluoroalkyl, a haloalkylamido, an isothiocyanate, an azide, a diazocarbonyl, a substituted oxirane, or a .beta.-chloroethylamine; R.sub.4 is a hydrogen, an alkyl, or is joined to R.sub.5 ; R.sub.5 is a hydrogen, a hydroxy, an alkoxy, an acyloxy, an amino, an alkylamino, a halogen, an alkyl, a haloalkyl, or is joined to R.sub.4 ; R.sub.6 is a hydrogen, an alkyl, or a haloalkyl; A.sub.1 and A.sub.2 is the same or different, each is direct link or an alkylene; X.sub.1 is an oxygen, a sulfur, a sulphinyl, a sulphonyl, an amino, an alkylimino, or an alkylene; R.sub.7 is a hydrogen, a halogen, an alkoxy, a haloalkoxy, an acyloxy, a haloacyloxy, an aryloxy, a thioalkyl, a thioraryl, an amino, an alkylimino, an alkylamido group, a haloalkylamido group, or a phenyl optionally substituted with a halogen, a nitro group, an alkyl, a haloalkyl, a cyano, a hydroxyl, a carboxylic group, an amino, an alkylamino group, a dialkylamino group, a bisalkylamino group, a haloalkylamino group, a dihaloalkylamino group, a bishaloalkylamino group, an acylamido group, a diacylamido group, an alkylacylamido group, a haloacylamido group, a bis(haloacyl)imido group, or an alkylhaloacylamido group. The present invention further relates to a method of producing the non-steroidal agonist compound, a composition containing the non-steroidal agonist compound, and methods of binding an androgen receptor, suppressing spermatogenesis, and providing hormonal therapy for androgen-dependent conditions.

Fungicidal compounds of the formula (I): ##STR1## in which A and B are independently H, fluoro, chloro, bromo, C.sub.1-4 alkyl, C.sub.1-4, alkoxy or halo (C.sub.1-4) alkyl provided that both are not H; D and E are independently H or fluoro; F.sup.1 is H, C.sub.1-4 alkyl or C.sub.1-4 akloxy; R.sup.2 is C.sub.1-4 alkyl, C.sub.1-4 alkoxy or optionally substituted phenyl, or R.sup.1 and R.sup.2 together with the nitrogen atom to which they are attached join to form a morpholine, piperidine, pyrrolidine or azetidine ring which is optionally substituted with C.sub.1-4 alkyl; R.sup.3 is H; R.sup.4 is trichloromethyl, C.sub.2-8 alkyl (optionally substituted with halogen, C.sub.1-8 alkoxy or R'S(O).sub.n in which R' is C.sub.1-4 alkyl, C.sub.2-4 alkenyl or C.sub.2-4 alkynyl and n is 0, 1 or 2), cyclopropyl (optionally substituted with halogen or C.sub.1-4 alkyl), C.sub.2-8 alkenyl, C.sub.2-8 alkynyl, C.sub.1-8 alkoxy, mono- or di(C.sub.1-4)alkyl- amino or the group, R"ON.dbd.C(CN) in which R" is C.sub. 1-4 alkyl, or R.sup.3 and R.sup.4 together with the group C(O)N to which they are attached join to form an azetidin-2-one ring which is optionally substituted with halogen or C.sub.1-4 alkyl; and X and Y are independently oxygen or sulphur.

The present invention relates to an antiandrogen compound and a method of treating prostate cancer in a patient utilizing the compound. The present invention also relates to a pharmaceutical composition which includes the compound.