Patent US933039A successfully refreshed from Google Patents.
Patent US5498795A successfully refreshed from Google Patents.
US5498795A
Expired / Lapsed
US
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Acetylenes disubstituted with hydroxyaryl and aryl or heteroaryl groups having retinoid-like biological activity
Assignee: Allergan Inc
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Filing: 1994-12-29
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Granted: 1996-03-12
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Expires: 2014-12-29
Abstract
Abstract Compounds of the formula ##STR1## wherein R 1 -R 3 and R 5 independently are hydrogen, lower alkyl of 1 to 6 carbons, branched chain alkyl or cycloalkyl of 3 to 15 carbons, lower alkyl substituted cycloalkyl of 3 to 15 carbons; R 4 is lower alkyl of 1 to 6 carbons, branched chain alkyl or cycloalkyl of 3 to 15 carbons or lower alkyl substituted cycloalkyl of 3 to 15 carbons; X is S or O; Y is a phenyl group, or heteroaryl selected from a group consisting of pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl, imidazolyl and oxazolyl, said groups being substituted with the R 5 group defined above; 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 alkylphenyl, 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, have retinoid-like biological activity.
Inventors
- 👤 Tae K. Song
- 👤 Roshantha A. Chandraratna
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 11:57
CPC Classifications
C; C07; C07C; C07C65/00; C07C65/01; C07C65/19; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/24; C07D213/54; C07D213/55; C07D309/00; C07D309/02; C07D309/08; C07D309/10; C07D309/12; C07D405/00; C07D405/02; C07D405/12
Claims Analysis
Total Claims: 37
Claim 1
Independent Claim
304 words
A compound of the formula ##STR8## wherein R 1 -R 3 and R 5 independently are hydrogen, lower alkyl of 1 to 6 carbons, branched chain alkyl or cycloalkyl of 3 to 15 carbons, lower alkyl substituted cycloalkyl of 3 to 15 carbons; R 4 is lower alkyl of 1 to 6 carbons, branched chain alkyl or cycloalkyl of 3 to 15 carbons or lower alkyl substituted cycloalkyl of 3 to 15 carbons; X is S or O; Y is a phenyl group, or heteroaryl selected from a group consisting of pyridyl, thienyl, furyl, pyridazinyl, pirimidinyl, pyrazinyl, thiazolyl, imidazolyl and oxazolyl, said groups being substituted with the R 5 group defined above; 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 alkylphenyl, 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.
Claim 2
Dependent Claim
304 words
A compound of the formula ##STR8## wherein R 1 -R 3 and R 5 independently are hydrogen, lower alkyl of 1 to 6 carbons, branched chain alkyl or cycloalkyl of 3 to 15 carbons, lower alkyl substituted cycloalkyl of 3 to 15 carbons; R 4 is lower alkyl of 1 to 6 carbons, branched chain alkyl or cycloalkyl of 3 to 15 carbons or lower alkyl substituted cycloalkyl of 3 to 15 carbons; X is S or O; Y is a phenyl group, or heteroaryl selected from a group consisting of pyridyl, thienyl, furyl, pyridazinyl, pirimidinyl, pyrazinyl, thiazolyl, imidazolyl and oxazolyl, said groups being substituted with the R 5 group defined above; 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 alkylphenyl, 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.
Claim 3
Dependent Claim
9 words
A compound of claim 1 wherein X is O.
Claim 4
Dependent Claim
12 words
A compound of claim 1 wherein R 1 -R 3 are hydrogen.
Claim 5
Dependent Claim
10 words
A compound of claim 1 wherein R 5 is hydrogen.
Claim 6
Dependent Claim
13 words
A compound of claim 3 wherein the hydroxyl substituted phenyl ring is 1,2,4-substituted.
Claim 7
Dependent Claim
13 words
A compound of claim 3 wherein the hydroxyl substituted phenyl ring is 1,2,5-substituted.
Claim 8
Dependent Claim
18 words
A compound of claim 1 where A is (CH 2 ) n where n is 0 to 3.
Claim 9
Dependent Claim
24 words
A compound of claim 1 where B is COOH or a pharamaceutically acceptable salt thereof, COOR 8 , or CONR 9 R 10 .
Claim 10
Dependent Claim
9 words
A compound of claim 1 where Y is phenyl.
Claim 11
Dependent Claim
9 words
A compound of claim 1 where Y is pyridyl.
Claim 12
Dependent Claim
265 words
A compound of the formula ##STR9## wherein R 1 -R 3 and R 5 independently are hydrogen, lower alkyl of 1 to 6 carbons, branched chain alkyl or cycloalkyl of 3 to 15 carbons, lower alkyl substituted cycloalkyl of 3 to 15 carbons; R 4 is lower alkyl of 1 to 6 carbons, branched chain alkyl or cycloalkyl of 3 to 15 carbons or lower alkyl substituted cycloalkyl of 3 to 15 carbons; 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 alkylphenyl, 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.
Claim 13
Dependent Claim
265 words
A compound of the formula ##STR9## wherein R 1 -R 3 and R 5 independently are hydrogen, lower alkyl of 1 to 6 carbons, branched chain alkyl or cycloalkyl of 3 to 15 carbons, lower alkyl substituted cycloalkyl of 3 to 15 carbons; R 4 is lower alkyl of 1 to 6 carbons, branched chain alkyl or cycloalkyl of 3 to 15 carbons or lower alkyl substituted cycloalkyl of 3 to 15 carbons; 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 alkylphenyl, 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.
Claim 14
Dependent Claim
15 words
A compound of claim 11 wherein R 1 -R 3 and R 5 are hydrogen.
Claim 15
Dependent Claim
30 words
A compound of claim 12 wherein A is (CH 2 ) n , n is 0, and B is COOR 8 , or COOH or a pharmaceutically acceptable salt thereof.
Claim 16
Dependent Claim
10 words
A compound of claim 13 wherein R 4 is t-butyl.
Claim 17
Dependent Claim
32 words
A compound of claim 14 wherein the hydroxyl group is in the 1-position, the t-butyl group is in the 2-position and the ethynyl group is in the 4-position of the phenyl ring.
Claim 18
Dependent Claim
21 words
A compound of claim 15 where B is COOC 2 H 5 , or COOH or a pharmaceutically acceptable salt thereof.
Claim 19
Dependent Claim
32 words
A compound of claim 14 wherein the hydroxyl group is in the 1-position, the t-butyl group is in the 2-position and the ethynyl group is in the 5-position of the phenyl ring.
Claim 20
Dependent Claim
15 words
A compound of claim 17 where B is COOH or a pharmaceutically acceptable salt thereof.
Claim 21
Dependent Claim
10 words
A compound of claim 13 wherein R 4 is 2-(1-adamantyl).
Claim 22
Dependent Claim
32 words
A compound of claim 19 wherein the hydroxyl group is in the 1-position, the 2-(1-adamantyl) group is in the 2-position and the ethynyl group is in the 4-position of the phenyl ring.
Claim 23
Dependent Claim
19 words
A compound of claim 20 where B is COOCH 3 , or COOH or a pharmaceutically acceptable salt thereof.
Claim 24
Dependent Claim
32 words
A compound of claim 19 wherein the hydroxyl group is in the 1-position, the 2-(1-adamantyl) group is in the 2-position and the ethynyl group is in the 5-position of the phenyl ring.
Claim 25
Dependent Claim
21 words
A compound of claim 22 wherein B is COOC 2 H 5 , or COOH or a pharmaceutically acceptable salt thereof.
Claim 26
Dependent Claim
265 words
A compound of the formula ##STR10## wherein R 1 -R 3 and R 5 independently are hydrogen, lower alkyl of 1 to 6 carbons, branched chain alkyl or cycloalkyl of 3 to 15 carbons, lower alkyl substituted cycloalkyl of 3 to 15 carbons; R 4 is lower alkyl of 1 to 6 carbons, branched chain alkyl or cycloalkyl of 3 to 15 carbons or lower alkyl substituted cycloalkyl of 3 to 15 carbons; 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 alkylphenyl, 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.
Claim 27
Dependent Claim
265 words
A compound of the formula ##STR10## wherein R 1 -R 3 and R 5 independently are hydrogen, lower alkyl of 1 to 6 carbons, branched chain alkyl or cycloalkyl of 3 to 15 carbons, lower alkyl substituted cycloalkyl of 3 to 15 carbons; R 4 is lower alkyl of 1 to 6 carbons, branched chain alkyl or cycloalkyl of 3 to 15 carbons or lower alkyl substituted cycloalkyl of 3 to 15 carbons; 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 alkylphenyl, 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.
Claim 28
Dependent Claim
15 words
A compound of claim 24 wherein R 1 -R 3 and R 5 are hydrogen.
Claim 29
Dependent Claim
30 words
A compound of claim 25 wherein A is (CH 2 ) n , n is 0, and B is COOR 8 , or COOH or a pharmaceutically acceptable salt thereof.
Claim 30
Dependent Claim
10 words
A compound of claim 26 wherein R 4 is t-butyl.
Claim 31
Dependent Claim
32 words
A compound of claim 27 wherein the hydroxyl group is in the 1-position, the t-butyl group is in the 2-position and the ethynyl group is in the 4-position of the phenyl ring.
Claim 32
Dependent Claim
20 words
A compound of claim 28 wherein B COOC 2 H 5 , or COOH or a pharmaceutically acceptable salt thereof.
Claim 33
Dependent Claim
32 words
A compound of claim 27 wherein the hydroxyl group is in the 1-position, the t-butyl group is in the 2-position and the ethynyl group is in the 5-position of the phenyl ring.
Claim 34
Dependent Claim
20 words
A compound of claim 30 wherein B is COOC 2 H 5 or COOH or a pharmaceutically acceptable salt thereof.
Claim 35
Dependent Claim
10 words
A compound of claim 26 wherein R 4 is 2-(1-adamantyl).
Claim 36
Dependent Claim
32 words
A compound of claim 32 wherein the hydroxyl group is in the 1-position, the 2-(1-adamantyl) group is in the 2-position and the ethynyl group is in the 5-position of the phenyl ring.
Claim 37
Dependent Claim
21 words
A compound of claim 33 wherein B is COOC 2 H 5 , or COOH or a pharmaceutically acceptable salt thereof.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1999-03-12 | 1999-09-11 | 2000-03-12 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2003-03-12 | 2003-09-11 | 2004-03-12 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2007-03-12 | 2007-09-11 | 2008-03-12 | $7700.00 | Window Closed / Lapsed |