US5616712A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Acetylenes disubstituted with a phenyl or heteroaryl group and a 2-thio-1,2,3,4-tetrahdroquinolinyl, 2-alkylthio-3,4-dihydroquinolinyl or 2-alkoxy-3,4-dihydroquinolinyl group having retinoid-like biological activity
Assignee: Allergan Inc
•
Filing: 1995-05-16
•
Granted: 1997-04-01
•
Expires: 2015-05-16
Abstract
Abstract Compounds of the formula ##STR1## where the symbols are defined as in the specification.
Inventors
- 👤 Min Teng
- 👤 Richard L. Beard
- 👤 Diana Colon
- 👤 Tien T. Duong
- 👤 Roshantha A. Chandraratna
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 10:27
CPC Classifications
C; C07; C07D; C07D215/00; C07D215/02; C07D215/16; C07D215/20; C07D215/22; C07D215/227; A; A61; A61P; A61P3/00; A61P3/02; C07D215/36
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
184 words
A compound of the formula ##STR8## wherein R 1 is lower alkyl of 1 to 10 carbons or benzyl; R 2 and R 3 are hydrogen, lower alkyl of 1-6 carbons, or halogen; R 4 is hydrogen, lower alkyl of 1-6 carbons, halogen, OR 11 , SR 11 , OCOR 11 , SCOR 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHCOR 11 or NR 11 COR 11 ; Y is phenyl or a heteroaryl group selected from a group consisting of pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl, imidazolyl and oxazolyl; n is 0-5, 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 5-10 carbons, or phenyl or lower alkylphenyl, R 11 is lower alkyl, phenyl or lower alkylphenyl.
Claim 2
Dependent Claim
184 words
A compound of the formula ##STR8## wherein R 1 is lower alkyl of 1 to 10 carbons or benzyl; R 2 and R 3 are hydrogen, lower alkyl of 1-6 carbons, or halogen; R 4 is hydrogen, lower alkyl of 1-6 carbons, halogen, OR 11 , SR 11 , OCOR 11 , SCOR 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHCOR 11 or NR 11 COR 11 ; Y is phenyl or a heteroaryl group selected from a group consisting of pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl, imidazolyl and oxazolyl; n is 0-5, 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 5-10 carbons, or phenyl or lower alkylphenyl, R 11 is lower alkyl, phenyl or lower alkylphenyl.
Claim 3
Dependent Claim
324 words
A compound of the formula ##STR9## wherein X is O; R 5 is lower alkyl of 1 to 10 carbons, lower alkenyl of 2 to 10 carbons, phenyl C 1 -C 6 lower alkyl, phenyl C 2 -C 6 lower alkenyl, heteroaryl C 1 -C 6 lower alkyl, heteroaryl C 2 -C 6 lower alkenyl; R 2 and R 3 are hydrogen, lower alkyl of 1-6 carbons, or halogen; R 4 is hydrogen, lower alkyl of 1-6 carbons, halogen, OR 11 , SR 11 , OCOR 11 , SCOR 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHCOR 11 or NR 11 COR 11 ; Y is phenyl or a heteroaryl group selected from a group consisting of pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl, imidazolyl and oxazolyl; 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 5-10carbons, 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 4
Dependent Claim
324 words
A compound of the formula ##STR9## wherein X is O; R 5 is lower alkyl of 1 to 10 carbons, lower alkenyl of 2 to 10 carbons, phenyl C 1 -C 6 lower alkyl, phenyl C 2 -C 6 lower alkenyl, heteroaryl C 1 -C 6 lower alkyl, heteroaryl C 2 -C 6 lower alkenyl; R 2 and R 3 are hydrogen, lower alkyl of 1-6 carbons, or halogen; R 4 is hydrogen, lower alkyl of 1-6 carbons, halogen, OR 11 , SR 11 , OCOR 11 , SCOR 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHCOR 11 or NR 11 COR 11 ; Y is phenyl or a heteroaryl group selected from a group consisting of pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl, imidazolyl and oxazolyl; 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 5-10carbons, 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 5
Dependent Claim
15 words
A compound in accordance with claim 2 wherein R 5 is lower alkyl or benzyl.
Claim 6
Dependent Claim
34 words
A compound in accordance with claim 3 wherein A is (CH 2 ) n , and B is COOH or a pharmaceutically acceptable salt thereof, COOR 8 , or CONR 9 R 10 .
Claim 7
Dependent Claim
11 words
A compound in accordance with claim 2 wherein X is 5.
Claim 8
Dependent Claim
15 words
A compound in accordance with claim 5 wherein R 5 is lower alkyl or benzyl.
Claim 9
Dependent Claim
34 words
A compound in accordance with claim 6 wherein A is (CH 2 ) n , and B is COOH or a pharmaceutically acceptable salt thereof, COOR 8 , or CONR 9 R 10 .
Claim 10
Dependent Claim
79 words
A compound of the formula ##STR10## where R 5 is lower alkyl of 1 to 10 carbons, or phenyl C 1 -C 6 lower alkyl; R 2 and R 3 are hydrogen, or lower alkyl of 1-6 carbons; R 4 is hydrogen, lower alkyl of 1-6 carbons, or halogen, and R' 8 is H, 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.
Claim 11
Dependent Claim
79 words
A compound of the formula ##STR10## where R 5 is lower alkyl of 1 to 10 carbons, or phenyl C 1 -C 6 lower alkyl; R 2 and R 3 are hydrogen, or lower alkyl of 1-6 carbons; R 4 is hydrogen, lower alkyl of 1-6 carbons, or halogen, and R' 8 is H, 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.
Claim 12
Dependent Claim
20 words
A compound in accordance with claim 8 wherein R 5 is lower alkyl of 1 to 10 carbons, or benzyl.
Claim 13
Dependent Claim
20 words
A compound in accordance with claim 9 wherein R 2 and R 3 are methyl and R 4 is H.
Claim 14
Dependent Claim
20 words
A compound in accordance with claim 10 wherein R' 8 is H, or lower alkyl of 1 to 6 carbons.
Claim 15
Dependent Claim
15 words
A compound in accordance with claim 11 wherein the phenyl group is 1,4 (para) substituted.
Claim 16
Dependent Claim
28 words
A compound in accordance with claim 12 which is: (1) ethyl 4-[(4,4-dimethyl-2-methylthio-3,4-dihydro-6-quinolinyl)ethynyl]benzoate; (2) ethyl 4-[(4,4-dimethyl-2-heptylthio-3,4-dihydro-6-quinolinyl)ethynyl]benzoate; (3) 4-(4,4-dimethyl-2-methylthio-3,4-dihydro-6-quinolinyl)ethynyl]benzoic acid; (4) 4-[(4,4-dimethyl-2-heptylthio-3,4-dihydro-6-quinolinyl)ethynyl]benzoic acid; (5) ethyl 4-[(4,4-dimethyl-2-methylthio-3,4-dihydro-7-quinolinyl)ethynyl]benzoate, and (6) 4-[(4,4-dimethyl-2-methylthio-3,4-dihydro-7-quinolinyl)ethynyl]benzoic acid.
Claim 17
Dependent Claim
79 words
A compound of the formula ##STR11## where R 5 is lower alkyl of 1 to 10 carbons, or phenyl C 1 -C 6 lower alkyl; R 2 and R 3 are hydrogen, or lower alkyl of 1-6 carbons; R 4 is hydrogen, lower alkyl of 1-6 carbons, or halogen, and R' 8 is H, 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.
Claim 18
Dependent Claim
79 words
A compound of the formula ##STR11## where R 5 is lower alkyl of 1 to 10 carbons, or phenyl C 1 -C 6 lower alkyl; R 2 and R 3 are hydrogen, or lower alkyl of 1-6 carbons; R 4 is hydrogen, lower alkyl of 1-6 carbons, or halogen, and R' 8 is H, 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.
Claim 19
Dependent Claim
21 words
A compound in accordance with claim 14 wherein R 5 is H, lower alkyl of 1 to 10 carbons, or benzyl.
Claim 20
Dependent Claim
20 words
A compound in accordance with claim 15 wherein R 2 and R 3 are methyl and R 4 is H.
Claim 21
Dependent Claim
20 words
A compound in accordance with claim 16 wherein R' 8 is H, or lower alkyl of 1 to 6 carbons.
Claim 22
Dependent Claim
15 words
A compound in accordance with claim 17 wherein the phenyl group is 1,4 (para) substituted.
Claim 23
Dependent Claim
22 words
A compound in accordance with claim 18 which is: (1) ethyl 4-[(4,4-dimethyl-2-iso-propoxy-3,4-dihydro-6-quinolinyl)ethynyl]benzoate; (2) 4-[(4,4-dimethyl-2-iso-propyloxy-3,4-dihydro-6-quinolinyl)ethynyl]benzoic acid; (3) ethyl 4-[(4,4-dimethyl-2-iso-propyloxy-3,4-dihydro-7-quinolinyl)ethynyl]benzoate, and (4) 4-[(4,4-dimethyl-2-iso-propyloxy-3,4-dihydro-7-quinolinyl)ethynyl]benzoic acid.
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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) | 2000-03-31 | 2000-09-30 | 2001-04-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2004-03-31 | 2004-09-30 | 2005-04-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2008-03-31 | 2008-09-30 | 2009-04-01 | $7700.00 | Window Closed / Lapsed |