US5175185A
Expired / Lapsed
US
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Acetylenes disubstituted with a heteroaromatic group and a substituted phenyl group having retinoid like activity
Assignee: Allergan Inc
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Filing: 1991-03-14
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Granted: 1992-12-29
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Expires: 2011-03-14
Abstract
Abstract Retinoid like activity is exhibited by compounds of the formula ##STR1## R 1 -R 3 independently are hydrogen, lower alkyl, cycloalkyl or lower alkenyl, A and A 1 independently are hydrogen, lower alkyl, cycloalkyl, lower alkenyl, SR 4 or OR 4 where R 4 is lower alkyl, cycloalkyl or lower alkenyl; Y is selected from a group consisting of thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl or oxazolyl; E is lower alkenyl, lower alkynyl, lower cycloalkyl, lower branched chain alkyl, or is characterized by the formula (CH 2 ) n where n is 0-5, and Z is H, OH, OR 5 , OCOR 5 , --COOH or a pharmaceutically acceptable salt, ester or amide thereof, --CH 2 OH, CH 2 OR 6 , CH 2 OCOR 6 , or --CHO, CH(OR 7 ) 2 , CHOR 8 O, or COR 9 , CR 9 (OR 7 ) 2 , CR 9 OR 8 O where R 5 is lower alkyl, phenyl or lower alkylphenyl, R 6 is lower alkyl, phenyl or lower alkylphenyl, R 7 is lower alkyl, R 8 is a divalent alkyl radical of 2-5 carbons, and R 9 is an alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons.
Inventors
- 👤 Roshantha A. S. Chandraratna
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 13:33
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/78; C07D213/79; C07D213/80
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
211 words
A compound of the formula ##STR16## wherein R 1 -R 3 independently are hydrogen, lower alkyl, cycloalkyl or lower alkenyl, A and A 1 independently are hydrogen, lower alkyl, cycloalkyl, lower alkenyl, SR 4 or OR 4 where R 4 is lower alkyl cycloalkyl or lower alkenyl, with the proviso that at least one of said R 1 -R 3 and A and A 1 groups is alkyl, thioalkyl or alkoxy group; Y is thienyl; E is divalent lower alkenyl, lower alkynyl, lower cycloalkyl, lower branched chain alkyl, or is characterized by the formula (CH 2 ) n where n is 0-5, and Z is H, OH, OR 5 , OCOR 5 , --COOH or a pharmaceutically acceptable salt, ester or amid thereof, --CH 2 OH, CH 2 OR 6 , CH 2 OCOR 6 , or --CHO, CH(OR 7 ) 2 , CHOR 8 O, or COR 9 or CR 9 (OR 7 ) 2 , CR 9 OR 8 O where R 5 is lower alkyl, phenyl or lower alkylphenyl, R 6 is lower alkyl, phenyl or lower alkylphenyl, R 7 is lower alkyl, R 8 is a divalent alkyl radical of 2-5 carbons, and E 9 is an alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons.
Claim 2
Dependent Claim
211 words
A compound of the formula ##STR16## wherein R 1 -R 3 independently are hydrogen, lower alkyl, cycloalkyl or lower alkenyl, A and A 1 independently are hydrogen, lower alkyl, cycloalkyl, lower alkenyl, SR 4 or OR 4 where R 4 is lower alkyl cycloalkyl or lower alkenyl, with the proviso that at least one of said R 1 -R 3 and A and A 1 groups is alkyl, thioalkyl or alkoxy group; Y is thienyl; E is divalent lower alkenyl, lower alkynyl, lower cycloalkyl, lower branched chain alkyl, or is characterized by the formula (CH 2 ) n where n is 0-5, and Z is H, OH, OR 5 , OCOR 5 , --COOH or a pharmaceutically acceptable salt, ester or amid thereof, --CH 2 OH, CH 2 OR 6 , CH 2 OCOR 6 , or --CHO, CH(OR 7 ) 2 , CHOR 8 O, or COR 9 or CR 9 (OR 7 ) 2 , CR 9 OR 8 O where R 5 is lower alkyl, phenyl or lower alkylphenyl, R 6 is lower alkyl, phenyl or lower alkylphenyl, R 7 is lower alkyl, R 8 is a divalent alkyl radical of 2-5 carbons, and E 9 is an alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons.
Claim 3
Dependent Claim
19 words
A compound of claim 1 wherein A and A 1 independently are hydrogen, lower alkyl, cycloalkyl, or lower alkenyl.
Claim 4
Dependent Claim
17 words
A compound of claim 2 wherein one of the A and A 1 groups is lower alkyl.
Claim 5
Dependent Claim
13 words
A compound of claim 3 wherein R 1 -R 3 all are hydrogen.
Claim 6
Dependent Claim
21 words
A compound of claim 2 wherein E is characterized by the formula (CH 2 ) n , where n is 0-5.
Claim 7
Dependent Claim
19 words
A compound of claim 2 where in Z is --COOH or a pharmaceutically acceptable salt, ester or amide thereof.
Claim 8
Dependent Claim
12 words
A compound of claim 6 wherein Z is a carboxylic acid ester.
Claim 9
Dependent Claim
27 words
A compound of claim 1 wherein one of the A and A 1 groups is R 4 where R 4 is lower alkyl, cycloalkyl or lower alkenyl.
Claim 10
Dependent Claim
13 words
A compound of claim 8 wherein R 1 -R 3 all are hydrogen.
Claim 11
Dependent Claim
20 words
A compound of claim 8 wherein E is characterized by the formula (CH 2 ) n where n is 0-5.
Claim 12
Dependent Claim
18 words
A compound of claim 8 wherein Z is --COOH or a pharmaceutically acceptable salt, ester or amide thereof.
Claim 13
Dependent Claim
11 words
A compound of claim 11 wherein Z is carboxylic acid ester.
Claim 14
Dependent Claim
22 words
A pharmaceutical composition comprising an effective amount of a compound set forth in claim 1, in combination with a pharmaceutically acceptable excipient.
Claim 15
Dependent Claim
9 words
A compound of claim 1 where Y is pyridazyl.
Claim 16
Dependent Claim
28 words
A compound of claim 1 where one of the A and A 1 groups is OR 4 , where R 4 is lower alkyl, cycloalkyl or lower alkenyl.
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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) | 1995-12-29 | 1996-06-29 | 1996-12-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1999-12-29 | 2000-06-29 | 2000-12-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2003-12-29 | 2004-06-29 | 2004-12-29 | $7700.00 | Window Closed / Lapsed |