Irreversible non-steroidal antagonist compound and its use in the treatment of prostate cancer

A method for treating prostate cancer in a patient comprising:

• administering to the patient an effective amount of a compound having the formula:
• 43
• where Z is NCS or CN;
• R is F, NH2, NCS, N3 or NHCOCH2Y;
• X is S or SO2;
• and
• Y is a halogen;
• wherein the compound binds irreversibly to an androgen receptor of the patient.

A compound having the formula:

• 45
• where Z is NCS or CN;
• R is F, NH2, NCS, N3 or NHCOCH2Y;
• X is S or SO2;
• and
• Y is a halogen.

A pharmaceutical composition comprising:

• a compound having the formula:
• 46
• wherein R1, R2 and R3, 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 β-chloroethylamine;
• R4 is a hydrogen, an alkyl, or is joined to R5;
• R5 is a hydrogen, a hydroxy, an alkoxy, an acyloxy, an amino, an alkylamino, a halogen, or is joined to R4;
• R6 is a hydrogen, an alkyl, or a halogenoalkyl;
• A1 and A2 is the same or different, each is direct link or alkylene;
• X1 is a halogen, an oxygen, a sulfur, a sulphinyl, a sulphonyl, an amino, an alkylimino, or an alkylene;
• and
• R7 is a hydrogen, a halogen, an alkoxy, a haloalkoxy, an acyloxy, a haloacyloxy, an aryloxy, a thioalkyl, a thioraryl, a sulphinyl, a haloalkyl sulphinyl, a sulphonyl, a haloalkylsulphonyl, an amino, an alkylimino, an alkylamido group, a haloalkylamido group, an isothiocyanate, an azide, a diazocarbonyl, a substituted oxirane, a β-chloroethylamine, 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, an alkylamido group, a haloalkylamido group, an isothiocyanate, an azide, a diazocarbonyl, a substituted oxirane, or a β-chloroethylamine;
• and
• a pharmaceutically acceptable carrier.