US4239776A
Expired / Lapsed
US
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Anti-androgenic amides
Assignee: Imperial Chemical Industries Ltd
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Filing: 1978-10-10
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Granted: 1980-12-16
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Expires: 1998-10-10
Abstract
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.
Inventors
- 👤 Alasdair T. Glen
- 👤 Richard W. Bayles
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 14:07
CPC Classifications
C; C07; C07C; C07C255/00; C07C255/49; A; A61; A61P; A61P25/00; A61P25/04
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
170 words
An acylanilide of the formula: ##STR7## wherein R 1 is cyano, nitro, trifluoromethyl or iodo, or has the formula --CONR 11 R 12 , and wherein R 2 is cyano, 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 at least one of R 1 and R 2 is cyano.
Claim 2
Dependent Claim
170 words
An acylanilide of the formula: ##STR7## wherein R 1 is cyano, nitro, trifluoromethyl or iodo, or has the formula --CONR 11 R 12 , and wherein R 2 is cyano, 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 at least one of R 1 and R 2 is cyano.
Claim 3
Dependent Claim
81 words
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
Dependent Claim
78 words
An acylanilide as claimed in claim 1 wherein R 1 is nitro or trifluoromethyl, R 2 is cyano, 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 5
Dependent Claim
5 words
The compound 3,4-dicyanoisobutyrylanilide or 3,4-dicyano-(2-hydroxy-2-methylpropionyl)anilide.
Claim 6
Dependent Claim
5 words
The compound 3,4-dicyanoisobutyrylanilide or 3,4-dicyano-(2-hydroxy-2-methylpropionyl)anilide.
Claim 7
Dependent Claim
3 words
The compound 3,4-dicyano-N-methylisobutyrylanilide.
Claim 8
Dependent Claim
3 words
The compound 3,4-dicyano-N-methylisobutyrylanilide.
Claim 9
Dependent Claim
5 words
The compound 3,4-dicyano-(2-methoxy-2-methylpropionyl)anilide or 4-cyano-3-trifluoromethyl-(2-hydroxy-2-methylpropionyl)anilide.
Claim 10
Dependent Claim
5 words
The compound 3,4-dicyano-(2-methoxy-2-methylpropionyl)anilide or 4-cyano-3-trifluoromethyl-(2-hydroxy-2-methylpropionyl)anilide.
Claim 11
Dependent Claim
28 words
A pharmaceutical or veterinary composition having antiandrogenic properties which comprises an effective amount of an acylanilide, claimed in claim 1, in association with a pharmaceutically-acceptable diluent or carrier.
Claim 12
Independent Claim
213 words
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 1 and R 2 is cyano and wherein the other of R 1 and R 2 is cyano, 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, hydroxy-alkyl 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 13
Independent Claim
213 words
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 1 and R 2 is cyano and wherein the other of R 1 and R 2 is cyano, 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, hydroxy-alkyl 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.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-12-16 | 1984-06-16 | 1984-12-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-12-16 | 1988-06-16 | 1988-12-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-12-16 | 1992-06-16 | 1992-12-16 | $7700.00 | Window Closed / Lapsed |