US5348975A
Expired / Lapsed
US
⏱️ 0.0 years remaining
7-chromanyl esters of phenols and benzoic acids having retinoid-like activity
Assignee: Allergan Inc
•
Filing: 1993-10-27
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Granted: 1994-09-20
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Expires: 2013-10-27
Abstract
Abstract Retinoid like activity is exhibited by compounds of the formula ##STR1## wherein the R 1 -R 6 groups are independently H or straight chain or branched chain lower alkyl or cycloalkyl of 1 to 6 carbons; X symbolizes an ester or thioester linkage, Y is lower branched chain alkyl having 2 to 6 carbons, cycloalkyl having 3 to 6 carbons or is (CH 2 ) n where n is an integer between 0 to 6 or is an alkenyl group of 2 to 6 carbons, and having 1 or 2 double bonds, or an alkynyl group of 2 to 6 carbons; and Z is H, OH, OR', OCOR', --COOH or a pharmaceutically acceptable salt COOR 8 , COONR 9 R 10 , --CH 2 OH, CH 2 OR 11 , CH 2 OCOR 11 , CHO, CH(OR 12 ), CHOR 13 O, --COR', CR'(OR 12 ) 2 , or CR'OR 13 O; where R' is an alky, cycloalkyl or alkenyl group containing 1-5 carbons, R 8 is an alkyl group of 1-10 carbons, or a cycloalkyl group of 5-10 carbons,, or R 8 is phenyl or lower alkylphenyl, R 9 and R 10 independently or hydrogen, an alkyl group of 1-10 carbons, or a cycloalkyl group of 5-10 carbons or phenyl or lower alkyl phenyl, R 11 is lower alkyl, and R 13 is a divalent alkyl radical of 2-5 carbons.
Inventors
- 👤 Roshantha A. S. Chandraratna
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 06:49
CPC Classifications
C; C07; C07D; C07D311/00; C07D311/02; C07D311/04; C07D311/58; A; A61; A61P; A61P17/00; A61P17/06; A61P17/10; A61P17/16; A61P19/00; A61P19/02; A61P27/00; A61P27/02; A61P37/00; A61P37/08
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
201 words
A compound of the formula ##STR16## wherein the R 1 -R 6 groups are independently H or straight chain or branched chain lower alkyl or cycloalkyl groups of up to 6 carbons; X is --COS--; Y is cycloalkyl or branched chain alkyl group of 3 to 6 carbons, or is (CH 2 ) n where n is an integer between 0 to 6, and Z is H, OH, OR', OCOR', --COOH or a pharmaceutically acceptable salt, 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', CR'(OR 12 ) 2 , or CR'OR 13 O where R' is an alkyl, cycloalkyl or alkenyl group containing up to 5 carbons, R 8 is an alkyl group of 1-10 carbons, or a cycloalkyl group of 5-10 carbons, or R 8 is phenyl or lower alkylphenyl, R 9 and R10 independently are hydrogen, an alkyl group of 1-10 carbons, or a cycloalkyl group of 5-10 carbons or phenyl or lower alkyl phenyl, R 11 is lower alkyl, R 12 is lower alkyl R 13 is divalent alkyl radical of 2 to 5 carbons.
Claim 2
Dependent Claim
201 words
A compound of the formula ##STR16## wherein the R 1 -R 6 groups are independently H or straight chain or branched chain lower alkyl or cycloalkyl groups of up to 6 carbons; X is --COS--; Y is cycloalkyl or branched chain alkyl group of 3 to 6 carbons, or is (CH 2 ) n where n is an integer between 0 to 6, and Z is H, OH, OR', OCOR', --COOH or a pharmaceutically acceptable salt, 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', CR'(OR 12 ) 2 , or CR'OR 13 O where R' is an alkyl, cycloalkyl or alkenyl group containing up to 5 carbons, R 8 is an alkyl group of 1-10 carbons, or a cycloalkyl group of 5-10 carbons, or R 8 is phenyl or lower alkylphenyl, R 9 and R10 independently are hydrogen, an alkyl group of 1-10 carbons, or a cycloalkyl group of 5-10 carbons or phenyl or lower alkyl phenyl, R 11 is lower alkyl, R 12 is lower alkyl R 13 is divalent alkyl radical of 2 to 5 carbons.
Claim 3
Dependent Claim
16 words
A compound of claim 1 where Y is (CH 2 ) n and n is zero.
Claim 4
Dependent Claim
18 words
A compound of claim 2 where Z is COOR 8 wherein R 8 is H or lower alkyl.
Claim 5
Dependent Claim
23 words
A compound of claim 1 wherein R 1 and R 2 are methyl, R 3 , R 4 and R 5 are hydrogen.
Claim 6
Dependent Claim
17 words
A compound of claim 1 wherein R 5 is attached to the 6-position of the chroman nucleus.
Claim 7
Dependent Claim
22 words
A compound of claim 1 wherein R 3 and R 4 are methyl, R 1 R 2 and R 5 are hydrogen.
Claim 8
Dependent Claim
17 words
A compound of claim 6 wherein R 5 is attached to the 6-position of the chroman nucleus.
Claim 9
Dependent Claim
21 words
A compound of claim 1 wherein R 1 , R 2 , R 3 , and R 4 all are methyl.
Claim 10
Dependent Claim
17 words
A compound of claim 8 wherein R 5 is attached to the 6-position of the chroman nucleus.
Claim 11
Dependent Claim
18 words
A pharmaceutical composition comprising one or more compounds set forth in claim 1 and a pharmaceutically acceptable excipient.
Claim 12
Dependent Claim
72 words
A compound of the formula ##STR17## wherein the R 1 -R 6 groups are independently H or straight chain or branched chain lower alkyl or cycloalkyl groups of up to 6 carbons; n is an integer between 0 to 6; W is COOR 8 and R 8 is H, or lower alkyl, or W is CONR 9 R 10 where R 9 and R10 independently are H or lower alkyl or phenyl.
Claim 13
Dependent Claim
72 words
A compound of the formula ##STR17## wherein the R 1 -R 6 groups are independently H or straight chain or branched chain lower alkyl or cycloalkyl groups of up to 6 carbons; n is an integer between 0 to 6; W is COOR 8 and R 8 is H, or lower alkyl, or W is CONR 9 R 10 where R 9 and R10 independently are H or lower alkyl or phenyl.
Claim 14
Dependent Claim
9 words
A compound of claim 11 wherein n is zero.
Claim 15
Dependent Claim
18 words
A compound of claim 11 wherein R 1 -R 4 groups are independently H or CH 3 .
Claim 16
Dependent Claim
18 words
A pharmaceutical composition comprising one or more compounds set forth in claim 11 and a pharmaceutically acceptable excipient.
Claim 17
Dependent Claim
67 words
A compound of the formula ##STR18## wherein R 1 -R 4 are independently H or CH 3 , R 5 is H or lower alkyl of 1-6 carbons; W is COOR 8 and R 8 is H, lower alkyl, phenyl or benzyl, or W is CONR 9 R 10 where R 9 and R 10 independently are H or lower alkyl, or a pharmaceutically acceptable salt thereof.
Claim 18
Dependent Claim
67 words
A compound of the formula ##STR18## wherein R 1 -R 4 are independently H or CH 3 , R 5 is H or lower alkyl of 1-6 carbons; W is COOR 8 and R 8 is H, lower alkyl, phenyl or benzyl, or W is CONR 9 R 10 where R 9 and R 10 independently are H or lower alkyl, or a pharmaceutically acceptable salt thereof.
Claim 19
Dependent Claim
13 words
A compound of claim 15 wherein R 1 -R 4 all are methyl.
Claim 20
Dependent Claim
32 words
A compound of claim 16 wherein R 5 is H or methyl and R 8 is H or lower alkyl, or pharmaceutically acceptable salt of the compounds where R 8 is H.
Claim 21
Dependent Claim
10 words
A compound of claim 17 wherein R 5 is H.
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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) | 1997-09-19 | 1998-03-21 | 1998-09-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2001-09-19 | 2002-03-21 | 2002-09-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2005-09-19 | 2006-03-21 | 2006-09-20 | $7700.00 | Window Closed / Lapsed |