US5677320A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Phenyl or heteroaryl and tetrahydronaphthyl substituted diene compounds having retinoid like biological activity
Assignee: Allergan Inc
•
Filing: 1997-01-09
•
Granted: 1997-10-14
•
Expires: 2017-01-09
Abstract
Abstract Compounds of Formula 1 ##STR1## wherein the symbols are as defined in the specification, have retinoid like biological activity.
Inventors
- 👤 Roshantha A. Chandraratna
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 12:28
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; C07F9/28; C07F9/54; C07F9/5428; A; A61; A61P; A61P3/00; A61P3/02; A61P43/00; C07C; C07C17/00; C07C17/093; C07C17/16; C07C45/00; C07C45/27; C07C45/29; C07C45/45; C07C45/46; C07C49/00; C07C49/76; C07C49/782; C07C49/792; C07C63/00; C07C63/66; C07C69/00; C07C69/76; C07D; C07D307/00; C07D307/02; C07D307/04; C07D307/18; C07D307/22; C07D307/34; C07D307/56; C07D307/68; C07D333/00; C07D333/02; C07D333/04; C07D333/26; C07D333/38
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
317 words
A compound of the formula ##STR6## wherein m is 1-4; R 1 -R 4 independently are hydrogen, lower alkyl of 1 to 6 carbons, Cl, Br, or I; R 5 is hydrogen, lower alkyl of 1 to 6 carbons, Cl, Br, I, lower alkoxy or lower thioalkoxy of 1-6 carbons; R 6 is hydrogen, lower alkyl, Cl, Br, I, OR 11 , SR 11 , OCOR 11 , SCOR 11 , NH2, NHR 11 , N(R 11 ) 2 , NHCOR 11 OR NR 11 --COR 11 ; R 20 is independently hydrogen or lower alkyl; Y is thiazolyl or oxazolyl; A is (CH 2 ) n where n is 0-5, lower branched chain alkyl having 3-6 carbons, cycloalkyl having 3-6 carbons, alkenyl having 2-6 carbons and 1 or 2 double bonds, alkynyl having 2-6 carbons and 1 or 2 triple bonds; B is hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR 8 , CONR 9 R 10 , --CH 2 OH, CH 2 OR 11 , CH 2 OCOR 11 , CHO, CH(OR 12 ) 2 , CHOR 13 O, --COR 7 , CR 7 (OR 12 ) 2 , or CR 7 OR 13 O, where R 7 is an alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons, R 8 is an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5 to 10 carbons, or R 8 is phenyl or lower alkylphenyl, R 9 and R 10 independently are hydrogen, an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5-10 carbons, or phenyl or lower aklylphenyl, R 11 is lower alkyl, phenyl or lower alkylphenyl, R 12 is lower alkyl, and R 13 is divalent alkyl radical of 2-5 carbons, with the proviso that the diene and A-B moieties are attached to adjacent carbon atoms of the aryl or heteroaryl group symbolized by Y.
Claim 2
Dependent Claim
317 words
A compound of the formula ##STR6## wherein m is 1-4; R 1 -R 4 independently are hydrogen, lower alkyl of 1 to 6 carbons, Cl, Br, or I; R 5 is hydrogen, lower alkyl of 1 to 6 carbons, Cl, Br, I, lower alkoxy or lower thioalkoxy of 1-6 carbons; R 6 is hydrogen, lower alkyl, Cl, Br, I, OR 11 , SR 11 , OCOR 11 , SCOR 11 , NH2, NHR 11 , N(R 11 ) 2 , NHCOR 11 OR NR 11 --COR 11 ; R 20 is independently hydrogen or lower alkyl; Y is thiazolyl or oxazolyl; A is (CH 2 ) n where n is 0-5, lower branched chain alkyl having 3-6 carbons, cycloalkyl having 3-6 carbons, alkenyl having 2-6 carbons and 1 or 2 double bonds, alkynyl having 2-6 carbons and 1 or 2 triple bonds; B is hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR 8 , CONR 9 R 10 , --CH 2 OH, CH 2 OR 11 , CH 2 OCOR 11 , CHO, CH(OR 12 ) 2 , CHOR 13 O, --COR 7 , CR 7 (OR 12 ) 2 , or CR 7 OR 13 O, where R 7 is an alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons, R 8 is an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5 to 10 carbons, or R 8 is phenyl or lower alkylphenyl, R 9 and R 10 independently are hydrogen, an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5-10 carbons, or phenyl or lower aklylphenyl, R 11 is lower alkyl, phenyl or lower alkylphenyl, R 12 is lower alkyl, and R 13 is divalent alkyl radical of 2-5 carbons, with the proviso that the diene and A-B moieties are attached to adjacent carbon atoms of the aryl or heteroaryl group symbolized by Y.
Claim 3
Dependent Claim
14 words
A compound in accordance with claim 1 wherein R 1 is H or methyl.
Claim 4
Dependent Claim
20 words
A compound in accordance with claim 1 wherein R 2 , R 3 and R 4 are H or methyl.
Claim 5
Dependent Claim
12 words
A compound in accordance with claim 1 wherein R 5 is H.
Claim 6
Dependent Claim
14 words
A compound in accordance with claim 1 wherein R 6 is hydrogen or methyl.
Claim 7
Dependent Claim
11 words
A compound in accordance with claim 1 wherein m is 2.
Claim 8
Dependent Claim
14 words
A compound in accordance with claim 1 wherein R 20 is H or methyl.
Claim 9
Dependent Claim
37 words
A compound in accordance with claim 1 where the A-B group is (CH 2 ) n --COOH, (CH 2 ) n --COOR 8 or (CH 2 ) n --CONR 9 R 10 , and n is 0.
Claim 10
Dependent Claim
65 words
A compound in accordance with claim 1 wherein m is 2, R 1 , R 2 , R 3 , R 4 , R 6 and R 20 are H or methyl, R 5 is H, the A-B group is (CH 2 ) n --COOH, (CH 2 ) n --COOR 8 or (CH 2 ) n --CONR 9 R 10 , and n is 0.
Claim 11
Dependent Claim
36 words
A method of treating a disease or condition of a mammal which is susceptible to treatment by a retinoid-like compound, with a pharmaceutical composition containing an effective amount of a compound in accordance with claim 1.
Claim 12
Dependent Claim
11 words
A compound in accordance with claim 1 where Y is thiazolyl.
Claim 13
Dependent Claim
11 words
A compound in accordance with claim 1 where Y is oxazolyl.
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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) | 2000-10-13 | 2001-04-14 | 2001-10-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2004-10-13 | 2005-04-14 | 2005-10-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2008-10-13 | 2009-04-14 | 2009-10-14 | $7700.00 | Window Closed / Lapsed |