US5475113A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Tetrahydronaphthyl and thiazole, oxazole or imidazole substituted ethene derivatives having retinoid-like activity, reduced skin toxicity and reduced teratogenecity
Assignee: Allergan Inc
•
Filing: 1994-06-15
•
Granted: 1995-12-12
•
Expires: 2014-06-15
Abstract
Abstract Compounds of the formula ##STR1## as herein defined, have retinoid-like activity and are substantially non-teratogenic and non-irritating to the skin.
Inventors
- 👤 Roshantha A. Chandraratna
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 00:28
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/78; C07D213/79; C07D213/80; A; A61; A61P; A61P17/00; A61P27/00; A61P29/00; A61P3/00; A61P3/02; A61P3/06; A61P35/00; A61P37/00; A61P37/02; A61P9/00; A61P9/10; C07D307/00; C07D307/02; C07D307/34; C07D307/56; C07D307/68; C07D311/00; C07D311/02; C07D311/74; C07D333/00; C07D333/02; C07D333/04; C07D333/26; C07D333/38
Claims Analysis
Total Claims: 35
Claim 1
Independent Claim
353 words
A compound of the formula ##STR11## where R 1 is lower alkyl, Cl, Br, or I; R 2 is H, lower alkyl, Cl, Br, or I; R 3 is lower alkyl, Cl, Br, I, OR 11 , SR 11 , OCOR 11 , SCOR 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHCOR 11 , or NR 11 --COR 11 ; R 5 and R 6 independently are H, lower alkyl, Cl, Br, I, lower alkoxy or lower thioalkoxy of 1 to 6 carbons; A is (CH 2 ) n where n is 0-5, lower branched chain alkyl having 3 to 6 carbons, cycloalkyl having 3 to 6 carbons, alkenyl having 2 to 6 carbons and 1 or 2 double bonds, alkynyl having 2 to 6 carbons and 1 or 2 triple bonds; B is 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 to 10 carbons, or phenyl or lower alkylphenyl, R 11 is alkyl of 1 to 10 carbons, phenyl or lower alkylphenyl, R 12 is lower alkyl, and R 13 is divalent alkyl radical of 2-5 carbons; R 2O is independently H or lower alkyl, and Y is oxazole, thiazole, imidazole, isothiazole or isoimidazole which may be optionally substituted on a carbon or on a nitrogen with an R 21 group which is lower alkyl, or SO 2 NR 22 R 23 where R 22 is lower alkyl and R 23 is hydrogen or lower alkyl.
Claim 2
Dependent Claim
353 words
A compound of the formula ##STR11## where R 1 is lower alkyl, Cl, Br, or I; R 2 is H, lower alkyl, Cl, Br, or I; R 3 is lower alkyl, Cl, Br, I, OR 11 , SR 11 , OCOR 11 , SCOR 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHCOR 11 , or NR 11 --COR 11 ; R 5 and R 6 independently are H, lower alkyl, Cl, Br, I, lower alkoxy or lower thioalkoxy of 1 to 6 carbons; A is (CH 2 ) n where n is 0-5, lower branched chain alkyl having 3 to 6 carbons, cycloalkyl having 3 to 6 carbons, alkenyl having 2 to 6 carbons and 1 or 2 double bonds, alkynyl having 2 to 6 carbons and 1 or 2 triple bonds; B is 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 to 10 carbons, or phenyl or lower alkylphenyl, R 11 is alkyl of 1 to 10 carbons, phenyl or lower alkylphenyl, R 12 is lower alkyl, and R 13 is divalent alkyl radical of 2-5 carbons; R 2O is independently H or lower alkyl, and Y is oxazole, thiazole, imidazole, isothiazole or isoimidazole which may be optionally substituted on a carbon or on a nitrogen with an R 21 group which is lower alkyl, or SO 2 NR 22 R 23 where R 22 is lower alkyl and R 23 is hydrogen or lower alkyl.
Claim 3
Dependent Claim
16 words
A compound of claim 1 wherein A is (CH 2 ) n and n is 0.
Claim 4
Dependent Claim
24 words
A compound of claim 1 wherein B is COOH or a pharmaceutically acceptable salt thereof, COOR 8 , or CONR 9 R 10 .
Claim 5
Dependent Claim
10 words
A compound of claim 1 wherein R 3 is methyl.
Claim 6
Dependent Claim
10 words
A compound of claim 1 wherein R 1 is methyl.
Claim 7
Dependent Claim
10 words
A compound of claim 1 wherein R 2 is hydrogen.
Claim 8
Dependent Claim
10 words
A compound of claim 1 wherein R 20 is methyl.
Claim 9
Dependent Claim
13 words
A compound of claim 1 wherein R 5 and R 6 are hydrogen.
Claim 10
Dependent Claim
9 words
A compound of claim 1 wherein Y is thiazole.
Claim 11
Dependent Claim
9 words
A compound of claim 1 wherein Y is imidazole.
Claim 12
Dependent Claim
18 words
A compound of claim 1 wherein Y is imidazole substituted on a nitrogen with the R 21 group.
Claim 13
Dependent Claim
9 words
A compound of claim 1 wherein Y is oxazole.
Claim 14
Dependent Claim
106 words
A compound of the formula ##STR12## where R 1 is lower alkyl; R 2 is H or lower alkyl; R 3 is lower alkyl, Cl, Br, or I, and B is COOH or a pharmaceutically acceptable salt thereof, COOR 8 , or CONR 9 R 10 , where 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 to 10 carbons, or phenyl or lower alkylphenyl.
Claim 15
Dependent Claim
106 words
A compound of the formula ##STR12## where R 1 is lower alkyl; R 2 is H or lower alkyl; R 3 is lower alkyl, Cl, Br, or I, and B is COOH or a pharmaceutically acceptable salt thereof, COOR 8 , or CONR 9 R 10 , where 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 to 10 carbons, or phenyl or lower alkylphenyl.
Claim 16
Dependent Claim
19 words
A compound of claim 13 where the thiazole ring is 2,5-substituted with the group B occupying the 5 position.
Claim 17
Dependent Claim
18 words
A compound of claim 14 where R 2 is H, and R 1 and R 3 are methyl.
Claim 18
Dependent Claim
21 words
A compound of claim 15 where B is COOH or a pharmaceutically acceptable salt thereof, or COOC 2 H 5 .
Claim 19
Dependent Claim
135 words
A compound of the formula ##STR13## where R 1 is lower alkyl; R 2 is H or lower alkyl; R 3 is lower alkyl, Cl, Br, or I, and B is COOH or a pharmaceutically acceptable salt thereof, COOR 8 , or CONR 9 R 10 , where 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 to 10 carbons, or phenyl or lower alkylphenyl, and R 21 is H, or lower alkyl, or SO 2 NR 22 R 23 where R 22 is lower alkyl and R 23 is hydrogen or lower alkyl.
Claim 20
Dependent Claim
135 words
A compound of the formula ##STR13## where R 1 is lower alkyl; R 2 is H or lower alkyl; R 3 is lower alkyl, Cl, Br, or I, and B is COOH or a pharmaceutically acceptable salt thereof, COOR 8 , or CONR 9 R 10 , where 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 to 10 carbons, or phenyl or lower alkylphenyl, and R 21 is H, or lower alkyl, or SO 2 NR 22 R 23 where R 22 is lower alkyl and R 23 is hydrogen or lower alkyl.
Claim 21
Dependent Claim
18 words
A compound of claim 17 where R 2 is H, and R 1 and R 3 are methyl.
Claim 22
Dependent Claim
19 words
A compound of claim 18 where the imidazole ring is 2,4 substituted with the B group occupying the 2-position.
Claim 23
Dependent Claim
12 words
A compound of claim 19 where R 21 is CH 3 .
Claim 24
Dependent Claim
21 words
A compound of claim 20 where B is COOH or a pharmaceutically acceptable salt thereof, or COOC 2 H 5 .
Claim 25
Dependent Claim
10 words
A compound of claim 19 where R 21 is H.
Claim 26
Dependent Claim
21 words
A compound of claim 22 where B is COOH or a pharmaceutically acceptable salt thereof, or COOC 2 H 5 .
Claim 27
Dependent Claim
16 words
A compound of claim 19 where R 21 is SO 2 N(CH 3 ) 2 .
Claim 28
Dependent Claim
21 words
A compound of claim 24 where B is COOH or a pharmaceutically acceptable salt thereof, or COOC 2 H 5 .
Claim 29
Dependent Claim
19 words
A compound of claim 18 where the imidazole ring is 2,5 substituted with the B group occupying the 5-position.
Claim 30
Dependent Claim
12 words
A compound of claim 26 where R 21 is CH 3 .
Claim 31
Dependent Claim
21 words
A compound of claim 27 where B is COOH or a pharmaceutically acceptable salt thereof, or COOC 2 H 5 .
Claim 32
Dependent Claim
10 words
A compound of claim 26 where R 21 is H.
Claim 33
Dependent Claim
21 words
A compound of claim 29 where B is COOH or a pharmaceutically acceptable salt thereof, or COOC 2 H 5 .
Claim 34
Dependent Claim
16 words
A compound of claim 26 where R 21 is SO 2 N(CH 3 ) 2 .
Claim 35
Dependent Claim
21 words
A compound of claim 31 where B is COOH or a pharmaceutically acceptable salt thereof, or COOC 2 H 5 .
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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) | 1998-12-11 | 1999-06-12 | 1999-12-12 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2002-12-11 | 2003-06-12 | 2003-12-12 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2006-12-11 | 2007-06-12 | 2007-12-12 | $7700.00 | Window Closed / Lapsed |