US5468879A
Expired / Lapsed
US
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Disubstituted acetylenes bearing heterobicyclic groups and heteroaromatic or phenyl groups having retinoid like activity
Assignee: Allergan Inc
•
Filing: 1993-09-24
•
Granted: 1995-11-21
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Expires: 2013-09-24
Abstract
Abstract Compounds of the formula ##STR1## where R 1 and R 2 , independently are alkyl groups having 2 to 8 carbons; R 3 is hydrogen or lower alkyl; X is S, O or N--R 4 where R 4 is hydrogen or lower alkyl; Y is phenyl or pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, and pyrazinyl; A is (CH 2 ) n where n is 0-5, or lower branched chain alkyl, 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 hydrogen, COOH or a salt thereof, COOR 5 , CONR 6 R 7 , --CH 2 OH, CH 2 OR 8 , CH 2 OCOR 8 , CHO, CH(OR 9 ) 2 , CHOR 10 O, --COR 11 , CR 11 (OR 9 ) 2 , or CR 11 OR 10 O, where R 5 is alkyl of 1 to 10 carbons, or cycloalkyl of 5 to 10 carbons, or R 5 is phenyl or lower alkylphenyl, R 6 and R 7 independently are hydrogen, alkyl of 1 to 10 carbons, or cycloalkyl of 5 to 10 carbons, or phenyl or lower alkylphenyl, R 8 is alkyl of 1 to 10 carbons, phenyl or lower alkylphenyl, R 9 is lower alkyl, R 10 is divalent alkyl radical of 2-5 carbons and R 11 is alkyl, cycloalkyl or alkenyl containing 1 to 5 carbons, have retinoic acid like activity.
Inventors
- 👤 Roshantha A. S. Chandraratna
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 01:09
CPC Classifications
C; C07; C07D; C07D335/00; C07D335/04; C07D335/06; A; A61; A61P; A61P13/00; A61P13/02; A61P15/00; A61P17/00; A61P27/00; A61P27/02; A61P29/00; A61P35/00; A61P37/00; A61P37/02; A61P37/06; A61P9/00; A61P9/10; C07D215/00; C07D215/02; C07D215/12; C07D311/00; C07D311/02; C07D311/04; C07D311/58; C07D401/00; C07D401/02; C07D401/06; C07D405/00; C07D405/02; C07D405/06; C07D407/00; C07D407/02; C07D407/06; C07D409/00; C07D409/02; C07D409/06
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
265 words
A compound of the formula ##STR11## wherein R 1 and R 2 , independently are n-alkyl groups having 2 to 8 carbons, or cyclo or branch-chained alkyl groups of 3 to 8 carbons; R 3 is hydrogen or lower alkyl; X is S, or O; Y is a heteroaryl group selected from a group consisting of thienyl and furyl; 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 hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR 5 , CONR 6 R 7 , --CH 2 OH, CH 2 OR 8 , CH 2 OCOR 8 , CHO, CH(OR 9 ) 2 , CHOR 10 O, --COR 11 , CR 11 (OR 9 ) 2 , or CR 11 OR 10 O, where R 5 is an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5 to 10 carbons, or R 5 is phenyl or lower alkylphenyl, R 6 and R 7 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 8 is alkyl of 1 to 10 carbons, phenyl or lower alkylphenyl, R 9 is lower alkyl, R 10 is divalent alkyl radical of 2-5 carbons and R 11 is an alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons.
Claim 2
Dependent Claim
265 words
A compound of the formula ##STR11## wherein R 1 and R 2 , independently are n-alkyl groups having 2 to 8 carbons, or cyclo or branch-chained alkyl groups of 3 to 8 carbons; R 3 is hydrogen or lower alkyl; X is S, or O; Y is a heteroaryl group selected from a group consisting of thienyl and furyl; 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 hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR 5 , CONR 6 R 7 , --CH 2 OH, CH 2 OR 8 , CH 2 OCOR 8 , CHO, CH(OR 9 ) 2 , CHOR 10 O, --COR 11 , CR 11 (OR 9 ) 2 , or CR 11 OR 10 O, where R 5 is an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5 to 10 carbons, or R 5 is phenyl or lower alkylphenyl, R 6 and R 7 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 8 is alkyl of 1 to 10 carbons, phenyl or lower alkylphenyl, R 9 is lower alkyl, R 10 is divalent alkyl radical of 2-5 carbons and R 11 is an alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons.
Claim 3
Dependent Claim
11 words
A compound in accordance with claim 1 where X is S.
Claim 4
Dependent Claim
11 words
A compound in accordance with claim 1 where X is O.
Claim 5
Dependent Claim
20 words
A compound in accordance with claim 1 where the R 1 and R 2 groups are identical with one another.
Claim 6
Dependent Claim
18 words
A compound in accordance with claim 1 where the R 1 and R 2 groups are both n-alkyl.
Claim 7
Dependent Claim
11 words
A compound in accordance with claim 1 where Y is thienyl.
Claim 8
Dependent Claim
202 words
A compound of the formula ##STR12## where R 1 and R 2 , independently are n-alkyl groups having 2 to 8 carbons; R 3 is hydrogen or lower alkyl; X is S or O; A is (CH 2 ) n where n is 0-5, and B is hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR 5 , CONR 6 R 7 , --CH 2 OH, CH 2 OR 8 , CH 2 OCOR 8 , CHO, CH(OR 9 ) 2 , CHOR 10 O, --COR 11 , CR 11 (OR 9 ) 2 , or CR 11 OR 10 O, where R 5 is an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5 to 10 carbons, or R 5 is phenyl or lower alkylphenyl, R 6 and R 7 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 8 is alkyl of 1 to 10 carbons, phenyl or lower alkylphenyl, R 9 is lower alkyl, R 10 is divalent alkyl radical of 2-5 carbons and R 11 is an alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons.
Claim 9
Dependent Claim
202 words
A compound of the formula ##STR12## where R 1 and R 2 , independently are n-alkyl groups having 2 to 8 carbons; R 3 is hydrogen or lower alkyl; X is S or O; A is (CH 2 ) n where n is 0-5, and B is hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR 5 , CONR 6 R 7 , --CH 2 OH, CH 2 OR 8 , CH 2 OCOR 8 , CHO, CH(OR 9 ) 2 , CHOR 10 O, --COR 11 , CR 11 (OR 9 ) 2 , or CR 11 OR 10 O, where R 5 is an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5 to 10 carbons, or R 5 is phenyl or lower alkylphenyl, R 6 and R 7 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 8 is alkyl of 1 to 10 carbons, phenyl or lower alkylphenyl, R 9 is lower alkyl, R 10 is divalent alkyl radical of 2-5 carbons and R 11 is an alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons.
Claim 10
Dependent Claim
11 words
A compound in accordance with claim 7 where X is S.
Claim 11
Dependent Claim
19 words
A compound in accordance with claim 8 where A is (CH 2 ) n and where n is O.
Claim 12
Dependent Claim
24 words
A compound in accordance with claim 9 where B is COOH, COOR 5 , CONR 6 R 7 or a pharmaceutically acceptable salt thereof.
Claim 13
Dependent Claim
11 words
A compound in accordance with claim 7 where X is O.
Claim 14
Dependent Claim
19 words
A compound in accordance with claim 11 where A is (CH 2 ) n and where n is O.
Claim 15
Dependent Claim
24 words
A compound in accordance with claim 12 where B is COOH, COOR 5 , CONR 6 R 7 or a pharmaceutically acceptable salt thereof.
Claim 16
Dependent Claim
37 words
A compound of the formula ##STR13## where where R 1 and R 2 are identical and are selected from the group consisting of ethyl, n-propyl and n-butyl; Z is CH, and R 5 is ethyl or hydrogen.
Claim 17
Dependent Claim
37 words
A compound of the formula ##STR13## where where R 1 and R 2 are identical and are selected from the group consisting of ethyl, n-propyl and n-butyl; Z is CH, and R 5 is ethyl or hydrogen.
Claim 18
Dependent Claim
13 words
A compound of claim 14 where R 1 and R 2 are ethyl.
Claim 19
Dependent Claim
9 words
A compound of claim 15 where Z is CH.
Claim 20
Dependent Claim
13 words
A compound of claim 14 where R 1 and R 2 are n-propyl.
Claim 21
Dependent Claim
9 words
A compound of claim 17 where Z is CH.
Claim 22
Dependent Claim
13 words
A compound of claim 14 where R 1 and R 2 are n-butyl.
Claim 23
Dependent Claim
9 words
A compound of claim 19 where Z is CH.
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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) | 1998-11-20 | 1999-05-22 | 1999-11-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2002-11-20 | 2003-05-22 | 2003-11-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2006-11-20 | 2007-05-22 | 2007-11-21 | $7700.00 | Window Closed / Lapsed |