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US4880839A
Expired / Lapsed
US
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Acyanilide derivatives
Assignee: Imperial Chemical Industries Ltd
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Filing: 1987-06-16
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Granted: 1989-11-14
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Expires: 2007-06-16
Abstract
Abstract An acylanilide of the formula: ##STR1## wherein R 1 or R 2 which may be the same or different, each is an electron-withdrawing substituent, alkylthio or phenylthio or R 1 is hydrogen, alkyl or alkoxy; wherein R 3 is hydrogen or halogen; wherein R 4 is hydrogen or acyl wherein A is branched-chain alkylene; and wherein R 5 is phenyl, substituted phenyl or naphthyl. The compounds possess progestational activity.
Inventors
- 👤 Howard Tucker
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 16:03
CPC Classifications
C; C07; C07C; C07C233/00; C07C233/01; C07C233/12; A; A61; A61P; A61P35/00
Claims Analysis
Total Claims: 8
Claim 1
Independent Claim
154 words
An acylanilide of the formula: ##STR5## wherein R 1 is 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 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; wherein A is branched-chain alkylene of up to 6 carbon atoms; and wherein R 5 is phenyl which is unsubstituted or which bears one, two or three substituents selected from halogen, nitro, hydroxy, carboxy, carbamoyl and alkyl, alkoxy, alkanoyl, alkylthio, alkylsulphinyl, alkylsulphonyl, perfluoroalkyl, perfluoroalkylthio, perfluoroalkylsulphinyl, perfluoroalkylsulphonyl, alkoxycarbonyl and N-alkylcarbamoyl each of up to 4 carbon atoms, and phenyl, phenylthio, phenylsulphinyl and phenylsulphonyl; or R 5 is naphthyl.
Claim 2
Dependent Claim
154 words
An acylanilide of the formula: ##STR5## wherein R 1 is 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 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; wherein A is branched-chain alkylene of up to 6 carbon atoms; and wherein R 5 is phenyl which is unsubstituted or which bears one, two or three substituents selected from halogen, nitro, hydroxy, carboxy, carbamoyl and alkyl, alkoxy, alkanoyl, alkylthio, alkylsulphinyl, alkylsulphonyl, perfluoroalkyl, perfluoroalkylthio, perfluoroalkylsulphinyl, perfluoroalkylsulphonyl, alkoxycarbonyl and N-alkylcarbamoyl each of up to 4 carbon atoms, and phenyl, phenylthio, phenylsulphinyl and phenylsulphonyl; or R 5 is naphthyl.
Claim 3
Dependent Claim
65 words
An acylanilide as claimed in claim 1, wherein R 1 and R 2 , which may be the same or different, each is nitro, trifluoromethyl, methylthio, methylsulphinyl, methylsulphonyl or chloro, R 3 and R 4 are both hydrogen, A is 2-methylethylene or 2,2-dimethylethylene and R 5 is phenyl which is unsubstituted or which bears one fluoro, chloro, hydroxy, methyl, nitro, methylthio, methylsulphinyl or methylsulphonyl substituent.
Claim 4
Dependent Claim
9 words
The compound N-(2-hydroxy-4-phenyl-2-trifluoromethylpentanoyl)-4-nitro-3-trifluoromethylaniline in either of its diastereoisomeric forms.
Claim 5
Dependent Claim
9 words
The compound N-(2-hydroxy-4-phenyl-2-trifluoromethylpentanoyl)-4-nitro-3-trifluoromethylaniline in either of its diastereoisomeric forms.
Claim 6
Dependent Claim
21 words
A pharmaceutical or veterinary composition comprising an acylanilide as claimed in claim 1 in association with a pharmaceutically-acceptable diluent or carrier.
Claim 7
Dependent Claim
66 words
A composition as claimed in claim 4 which is in a form suitable for oral dosage, as a tablet, capsule, aqueous or oily solution or suspension or emulsion; or 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 for anal or vaginal administration.
Claim 8
Dependent Claim
33 words
A method for producing a progestational effect in a warm-blooded animal, which comprises administering to said animal in need thereof an effective amount of at least one acylanilide as claimed in claim 1.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1992-11-13 | 1993-05-15 | 1993-11-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1996-11-13 | 1997-05-15 | 1997-11-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2000-11-13 | 2001-05-15 | 2001-11-14 | $7700.00 | Window Closed / Lapsed |