Anti-androgenic amides
AssigneeImperial Chemical Industries PLC
InventorsAlasdair T. Glen, Richard W. Bayles
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Abstract
The disclosure relates to novel 3,4-disubstituted-branched-chain-acylanilides, processes for their manufacture and pharmaceutical compositions containing them. The compounds possess anti-androgenic activity. Representative of the compounds disclosed is 3,4-dicyanoisobutyranilide.
Claims8
An acylanilide of the formula:
- ##STR7## wherein R.sup.1 is cyano, nitro, trifluoromethyl or iodo, or has the formula --CONR.sup.11 R.sup.12, and wherein R.sup.2 is cyano, nitro, trifluoromethyl, chloro, bromo or iodo, or has the formula --CONR.sup.11 R.sup.12, wherein R.sup.11 and R.sup.12, which may be the same or different, each is hydrogen or alkyl of up to 4 carbon atoms;
- wherein R.sup.3 is hydrogen or alkyl of up to 4 carbon atoms;
- wherein either R.sup.4 and R.sup.5, which may be the same or different, each is alkyl of up to 4 carbon atoms;
- or R.sup.4 and R.sup.5 are joined together with the adjacent carbon atom to form cycloalkyl of 3 or 4 carbon atoms;
- and wherein R.sup.6 is hydrogen, hydroxy, halogen, alkyl, hydroxyalkyl or alkoxy each of up to 4 carbon atoms, or acyloxy of up to 15 carbon atoms provided that at least one of R.sup.1 and R.sup.2 is cyano.
The compound 3,4-dicyanoisobutyrylanilide or 3,4-dicyano-(2-hydroxy-2-methylpropionyl)anilide.
The compound 3,4-dicyano-N-methylisobutyrylanilide.
The compound 3,4-dicyano-(2-methoxy-2-methylpropionyl)anilide or 4-cyano-3-trifluoromethyl-(2-hydroxy-2-methylpropionyl)anilide.
A method of producing an antiandrogenic effect in a warm-blooded animal in need of such an effect which comprises administering to said animal an effective amount of an acylanilide of the formula:
- ##STR8## wherein at least one of R.sup.1 and R.sup.2 is cyano and wherein the other of R.sup.1 and R.sup.2 is cyano, nitro, trifluoromethyl, chloro, bromo or iodo, or has the formula --CONR.sup.11 R.sup.12, wherein R.sup.11 and R.sup.12, which may be the same or different, each is hydrogen or alkyl of up to 4 carbon atoms;
- wherein R.sup.3 is hydrogen or alkyl of up to 4 carbon atoms;
- wherein either R.sup.4 and R.sup.5, which may be the same or different, each is alkyl of up to 4 carbon atoms;
- or R.sup.4 and R.sup.5 are joined together with the adjacent carbon atom to form cycloalkyl of 3 or 4 carbon atoms;
- and wherein R.sup.6 is hydrogen, hydroxy, halogen, alkyl, hydroxy-alkyl or alkoxy each of up to 4 carbon atoms, or acyloxy of up to 15 carbon atoms;
- provided that when R.sup.2 is cyano;
- R.sup.3 and R.sup.6 are both hydrogen and R.sup.4 and R.sup.5 are both methyl, R.sup.1 is not chloro.
Dependencies are inferred from the claim text.