US4535092A
Expired / Lapsed
US
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Acylanilides having antiandrogenic activity
Assignee: Imperial Chemical Industries Ltd
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Filing: 1982-11-01
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Granted: 1985-08-13
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Expires: 2002-11-01
Abstract
Abstract Acylanilides of the formula <IMAGE> wherein R1, R2 and R3 are substituents defined in claim 1; wherein R4 is hydrogen or alkyl of up to 4 carbon atoms, or is joined to R5 as stated below; wherein R5 is hydrogen, hydroxy, or alkoxy or acyloxy each of up to 15 carbon atoms, or is joined to R4 to form an oxycarbonyl group such that together with the -N-CO-C- part of the molecule it forms an oxazolidinedione group; wherein R6 is alkyl or halogenoalkyl of up to 4 carbon atoms; and wherein R7 is 5- or 6- membered saturated or unsaturated heterocyclic which contains one, two or three hetero atoms selected from oxygen, nitrogen and sulphur, which heterocyclic may be a single ring or may be fused to a benzo-ring, and which heterocyclic is unsubstituted or bears one or two substituents defined in claim 1; processes for their manufacture and pharmaceutical compositions containing them. The compounds possess antiandrogenic activity.
Inventors
- 👤 Leslie R. Hughes
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 03:34
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/62; C07D213/70; A; A61; A61P; A61P5/00; C07D213/24; C07D213/54; C07D213/55; C07D213/56; C07D213/61; C07D213/63; C07D213/64; C07D213/78; C07D213/84; C07D213/89; C07D239/00; C07D239/02; C07D239/24; C07D239/26; C07D277/00; C07D277/02; C07D277/20; C07D277/22; C07D277/30; C07D277/32; C07D277/34; C07D277/36; C07D277/60; C07D277/62; C07D277/64; C07D307/00; C07D307/02; C07D307/34; C07D307/56; C07D307/64; C07D333/00; C07D333/02; C07D333/04; C07D333/06; C07D333/24; C07D333/26; C07D333/28; C07D333/30; C07D333/34; C07D333/38; C07D339/00; C07D339/08
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
162 words
An acylanilide of the formula: ##STR10## wherein R 1 is cyano, carbamoyl, nitro, fluoro, chloro, bromo, iodo or hydrogen, or alkyl, alkoxy, alkanoyl, alkylthio, alkylsulphinyl, alkylsulphonyl, perfluoroalkyl, perfluoroalkylthio, perfluoroalkylsulphinyl or perfluoroalkylsulphonyl each of up to 4 carbon atoms, or phenylthio, phenylsulphinyl or phenylsulphonyl; wherein R 2 is cyano, carbamoyl, nitro, fluoro, chloro, bromo or iodo, or alkanoyl, alkylthio, alkylsulphinyl, alkylsulphonyl, perfluoroalkyl, perfluoroalkylthio, perfluoroalkylsulphinyl or perfluoroalkylsulphonyl each of up to 4 carbon atoms, or phenylthio, phenylsulphinyl or phenylsulphonyl; wherein R 3 is hydrogen or halogen; wherein R 4 is hydrogen or alkyl of up to 4 carbon atoms; wherein R 5 is hydrogen, hydroxy, or alkoxy or acyloxy each of up to 15 carbon atoms; wherein R 6 is alkyl or halogenalkyl of up to 4 carbon atoms; and wherein R 7 is thienyl which is unsubstituted or bears one or two substituents selected from the group consisting of halogen, cyano, alkoxy, alkylthio, alkylsulphonyl each of up to 4 carbon atoms or trifluoromethyl.
Claim 2
Dependent Claim
162 words
An acylanilide of the formula: ##STR10## wherein R 1 is cyano, carbamoyl, nitro, fluoro, chloro, bromo, iodo or hydrogen, or alkyl, alkoxy, alkanoyl, alkylthio, alkylsulphinyl, alkylsulphonyl, perfluoroalkyl, perfluoroalkylthio, perfluoroalkylsulphinyl or perfluoroalkylsulphonyl each of up to 4 carbon atoms, or phenylthio, phenylsulphinyl or phenylsulphonyl; wherein R 2 is cyano, carbamoyl, nitro, fluoro, chloro, bromo or iodo, or alkanoyl, alkylthio, alkylsulphinyl, alkylsulphonyl, perfluoroalkyl, perfluoroalkylthio, perfluoroalkylsulphinyl or perfluoroalkylsulphonyl each of up to 4 carbon atoms, or phenylthio, phenylsulphinyl or phenylsulphonyl; wherein R 3 is hydrogen or halogen; wherein R 4 is hydrogen or alkyl of up to 4 carbon atoms; wherein R 5 is hydrogen, hydroxy, or alkoxy or acyloxy each of up to 15 carbon atoms; wherein R 6 is alkyl or halogenalkyl of up to 4 carbon atoms; and wherein R 7 is thienyl which is unsubstituted or bears one or two substituents selected from the group consisting of halogen, cyano, alkoxy, alkylthio, alkylsulphonyl each of up to 4 carbon atoms or trifluoromethyl.
Claim 3
Dependent Claim
66 words
An acylanilide as claimed in claim 1 wherein R 1 and R 2 , which may be the same or different, each is cyano, nitro, trifluoromethyl or chloro, R 3 and R 4 are both hydrogen, R 5 is hydroxy, R 6 is methyl, and R 7 is 2-thienyl, 3-thienyl, which may be unsubstituted or may bear one halogen, cyano, alkoxy, alkylthio, alkylsulphonyl or trifluoromethyl substituent.
Claim 4
Dependent Claim
5 words
The compound 4-nitro-3-trifluoromethyl- or 4-cyano-3-trifluoromethyl-N-[2-hydroxy-2-(5-methanesulphonylthien-2-yl)propionyl]aniline.
Claim 5
Dependent Claim
5 words
The compound 4-nitro-3-trifluoromethyl- or 4-cyano-3-trifluoromethyl-N-[2-hydroxy-2-(5-methanesulphonylthien-2-yl)propionyl]aniline.
Claim 6
Dependent Claim
10 words
An acylanilide according to claim 1, said acylanilide being 3-chloro-4-cyano-N-[2-hydroxy-2-(5-methanesulphonylthien-2-yl)-propionyl]aniline.
Claim 7
Dependent Claim
10 words
An acylanilide according to claim 1, said acylanilide being 4-nitro-3-trifluoromethyl-N-[2-hydroxy-2-(5-methanesulphonylthien-2-yl)propionyl]aniline.
Claim 8
Dependent Claim
10 words
An acylanilide according to claim 1, said acylanilide being 4-cyano-3-trifluoromethyl-N-[2-hydroxy-2-(5-methanesulphonylthien-2-yl)propionyl]aniline.
Claim 9
Dependent Claim
25 words
A pharmaceutical or veterinary composition which comprises an effective amount of an acylanilide, claimed in claim 1, in association with a pharmaceutically-acceptable diluent or carrier.
Claim 10
Dependent Claim
60 words
A composition as claimed in claim 7 which is in a form suitable for oral dosage, as a tablet, capsule, aqueous or oily solution or suspension or emulsion; in the form of a sterile solution or suspension suitable for parenteral administration, or in the form of an ointment or lotion for topical administration, or in the form of a suppository.
Claim 11
Dependent Claim
31 words
A method for producing an antiandrogenic effect in a warm-blooded animal in need of such treatment which comprises administering to said animal an effective amount of acylanilide claimed in claim 1.
References Cited (Backward Citations)
US1878543A
Cited
US2721216A
Cited
GB828695A
Cited
CH345016A
Cited
US3255231A
Cited
DE1160431B
Cited
US3282939A
Cited
US3419563A
Cited
US3632829A
Cited
US3706796A
Cited
US3933886A
Cited
JPS49135048A
Cited
US4049713A
Cited
US4191775A
Cited
US4291049A
Cited
US4386080A
Cited
EP0071535A1
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-08-12 | 1989-02-11 | 1989-08-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-08-12 | 1993-02-11 | 1993-08-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-08-12 | 1997-02-11 | 1997-08-13 | $7700.00 | Window Closed / Lapsed |