US4532343A
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Aromatic retinoic acid analogues
Assignee: SRI International Inc
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Filing: 1982-11-19
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Granted: 1985-07-30
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Expires: 2002-11-19
Abstract
Abstract Aromatic retinoic acid analogues of the formula <IMAGE> where X is hydrogen or fluorine, Y is hydrogen, halogen of atomic number 9 or 17, hydroxy, alkyl of 1 to 2 carbon atoms or alkoxy of 1 to 2 carbon atoms and R is hydroxy, alkoxy, aroxy, or NR1R2 where R1 is hydrogen, alkyl, or aryl and R2 is alkyl or aryl, with the proviso that when Y is hydrogen, X is fluorine. These retinoids are useful as chemopreventive agents for inhibiting tumor promotion in epithelial cells and for treating nonmalignant skin disorders.
Inventors
- 👤 Marcia I. Dawson
- 👤 Peter D. Hobbs
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 11:17
CPC Classifications
C; C07; C07C; C07C403/00; C07C403/20; A; A61; A61P; A61P35/00; C07C2601/00; C07C2601/12; C07C2601/16
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
60 words
A compound of the formula: ##STR5## where X is H or F, Y is H, F, Cl, hydroxy, methyl, ethyl, methoxy or ethoxy, and R is hydroxyl, alkoxy, aroxy, or NR 1 R 2 where R 1 is hydrogen, alkyl, or aryl and R 2 is alkyl or aryl, with the proviso that when Y is H, X is F.
Claim 2
Dependent Claim
60 words
A compound of the formula: ##STR5## where X is H or F, Y is H, F, Cl, hydroxy, methyl, ethyl, methoxy or ethoxy, and R is hydroxyl, alkoxy, aroxy, or NR 1 R 2 where R 1 is hydrogen, alkyl, or aryl and R 2 is alkyl or aryl, with the proviso that when Y is H, X is F.
Claim 3
Dependent Claim
76 words
The compound of claim 1 wherein the alkoxy group represented by R contains 1 to about 8 carbon atoms, the aroxy group represented by R contains 6 to about 15 carbon atoms, the alkyl groups represented by R 1 and R 2 each contain 1 to about 8 carbon atoms and have 0 to 1 hydroxy substituent, and the aryl groups represented by R 1 and R 2 each contain 6 to about 15 carbon atoms.
Claim 4
Dependent Claim
79 words
The compound of claim 1 wherein the alkoxy group represented by R contains 1 to 4 carbon atoms, the aroxy group represented by R is phenoxy, monohydroxyphenoxy, or monoalkoxyphenoxy where the alkoxy group contains 1 to 4 carbon atoms, the alkyl groups represented by R 1 and R 2 each contain 1 to 4 carbon atoms and have 0 or 1 hydroxy substituent, and the aryl groups represented by R 2 and R 3 are phenyl, 4-hydroxyphenyl, or 4-methoxyphenyl.
Claim 5
Dependent Claim
77 words
The compound of claim 1 where (a) R is ethoxy, X is fluorine, and Y is hydrogen; or (b) R is hydroxy, X is fluorine, and Y is hydrogen; or (c) R is ethoxy, X is hydrogen, and Y is methoxy; or (d) R is hydroxy, X is hydrogen and Y is methoxy; or (e) R is ethoxy, X is hydrogen, and Y is fluorine; or (f) R is hydroxy, X is hydrogen, and Y is fluorine.
Claim 6
Dependent Claim
20 words
A pharmaceutical composition comprising a pharmaceutically effective amount of the compound of claim 1 combined with a pharmaceutically acceptable carrier.
Claim 7
Dependent Claim
32 words
A chemopreventive composition for inhibiting tumor promotion in epithelial cells in a living animal comprising a tumor promotion inhibiting amount of the compound of claim 1 combined with a pharmaceutically acceptable carrier.
Claim 8
Dependent Claim
26 words
A therapeutic composition for treating a nonmalignant skin disorder comprising a therapeutically effective amount of the compound of claim 1 combined with a pharmaceutically acceptable carrier.
Claim 9
Dependent Claim
29 words
A method of inhibiting tumor promotion in epithelial cells of a living animal comprising administering a tumor promotion inhibiting amount of the compound of claim 1 to the animal.
Claim 10
Dependent Claim
11 words
The method of claim 8 where the animal is a human.
Claim 11
Dependent Claim
83 words
The method of claim 8 where the animal is a human and (a) R is ethoxy, X is fluorine, and Y is hydrogen, or (b) R is hydroxy, X is fluorine, and Y is hydrogen, or (c) R is ethoxy, X is hydrogen, and Y is methoxy, or (d) R is hydroxy, X is hydrogen, and Y is methoxy, or (e) R is ethoxy, X is hydrogen, and Y is fluorine, or (f) R is hydroxy, X is hydrogen, and Y is fluorine.
Claim 12
Dependent Claim
27 words
A method of treating a living animal for a nonmalignant skin disorder comprising administering a therapeutically effective amount of the compound of claim 1 to the animal.
Claim 13
Dependent Claim
11 words
The method of claim 11 where the animal is a human.
Claim 14
Dependent Claim
83 words
The method of claim 11 where the animal is a human and (a) R is ethoxy, X is fluorine, and Y is hydrogen, or (b) R is hydroxy, X is fluorine, and Y is hydrogen, or (c) R is ethoxy, X is hydrogen, and Y is methoxy, or (d) R is hydroxy, X is hydrogen, and Y is methoxy, or (e) R is ethoxy, X is hydrogen, and Y is fluorine, or (f) R is hydroxy, X is hydrogen, and Y is fluorine.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-07-29 | 1989-01-28 | 1989-07-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-07-29 | 1993-01-28 | 1993-07-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-07-29 | 1997-01-28 | 1997-07-30 | $7700.00 | Window Closed / Lapsed |