Acylanilides, process for their manufacture and pharmaceutical and veterinary compositions containing them

Claim 2

An acylanilide of the formula:- wherein at least one of R 1 and R 2 is cyano and wherein the other of R 1 and R 2 is tyano, nitro, trifluoromethyl, chloro, bromo or iodo, or has the formula -CONR 11 R 12 , wherein R 11 and R 12 , which may be the same or different, each is hydrogen or alkyl of up to 4 carbon atoms; wherein R 3 is hydrogen or alkyl of up to 4 carbon atoms; wherein either R 4 and R 5 , which may be the same or different, each is alkyl of up to 4 carbon atoms; or R 4 and R 5 are joined together with the adjacent carbon atom to form cycloalkyl of 3 or 4 carbon atoms; and wherein R 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 when R 2 is cyano, R 3 and R 6 are both hydrogen and R 4 and R 5 are both methyl, R 1 is not chloro.

Claim 3

An acylanilide as claimed in claim 1 wherein R 1 is cyano, R 2 is cyano, chloro, bromo, iodo or nitro, R 3 is hydrogen or alkyl of up to 4 carbon atoms, either R 4 is methyl or ethyl and R 5 is methyl or ethyl, or R 4 and R 5 together with the adjacent carbon atom form cyclopropyl, and R 6 is hydrogen, hydroxy, chloro, bromo, methyl, hydroxymethyl or methoxy, or alkanoyloxy of up to 12 carbon atoms.

Claim 4

An acylanilide as claimed in claim 1 wherein R1 is nitro cr trifluoromethyl, R 2 is cyano and R 3 , R , R and R 6 have the meanings stated in claim 2.

Claim 5

The compound 3,4-dicyanoisobutyrylanilide or 3,4-dicyano-(2-hydroxy-2-methylpropionyl)anilide.

Claim 6

The compound 3,4-dicyanoisobutyrylanilide or 3,4-dicyano-(2-hydroxy-2-methylpropionyl)anilide.

Claim 7

The compound 3,4-dicyano-N-methyl- isobutyrylanilide.

Claim 8

The compound 3,4-dicyano-N-methyl- isobutyrylanilide.

Claim 9

The compound 3,4-dicyano-(2-methoxy-2-methylpropionyl)anilide or 4-cyano-3-trifluoromethyl-(2-hydroxy-2-methylpropionyl)anilide.

Claim 10

The compound 3,4-dicyano-(2-methoxy-2-methylpropionyl)anilide or 4-cyano-3-trifluoromethyl-(2-hydroxy-2-methylpropionyl)anilide.

Claim 11

A process for the manufacture of an acylanilide, claimed in any of claims 1 to 6, which comprises either the reaction of an amine of the formula wherein R l , R 2 and R 3 have the meanings stated in claim 1, 2 or 3,with an acid of the formula HOCOCR 4 R 5 R 6 wherein R 4 , R 5 and R 6 have the meanings stated in claim 1, 2 or 3, or with a reactive derivative of said acid; or, for the manufacture of an acylanilide wherein R 6 is hydroxy, the Smiles' rearrangement of an amide of the formula:- wherein R l , R 2 , R 3 , R 4 and R 5 have the meanings stated above; whereafter an acylanilide wherein R 3 is hydrogen may be alkylated to provide the corresponding acylanilide wherein R 3 is alkyl of up to 4 carbon atoms; or an acylanilide wherein R 6 is hydroxy may be acylated to provide the corresponding acylanilide wherein R 6 is acyloxy of up to 15 carbon atoms; or an acylanilide wherein R 6 is acyloxy may be hydrolysed to the corresponding acylanilide wherein R 6 is hydroxy.

Claim 12

A pharmaceutical or veterinary composition which comprises an acylanilide, claimed in any of claims 1 to 6, in association with a pharmaceutically-acceptable diluent or carrier.

Claim 13

A composition as claimed in claim 8 which additionally contains one or more drugs selected from antioestrogens, progestins, inhibitors of gonadotrophin secretion, cytotoxi agents, antibiotics, and antiinflammatory agents.