Patent US2447024A successfully refreshed from Google Patents.
Patent US5489584A successfully refreshed from Google Patents.
US5489584A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Acetylenes disubstituted with a 5-amino or substituted 5-amino substituted tetrahydronaphthyl group and with an aryl or heteroaryl group having retinoid-like biological activity
Assignee: Allergan Inc
•
Filing: 1994-12-29
•
Granted: 1996-02-06
•
Expires: 2014-12-29
Abstract
Abstract Compounds of the formula ##STR1## having retinoid like biological activity.
Inventors
- 👤 Vidyasagar Vuligonda
- 👤 Richard L. Beard
- 👤 Roshantha A. Chandraratna
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 03:06
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/78; C07D213/79; C07D213/80; C07C; C07C17/00; C07C17/093; C07C17/10; C07C17/26; C07C17/263; C07C17/35; C07C229/00; C07C229/46; C07C229/52; C07C233/00; C07C233/57; C07C233/58; C07C251/00; C07C251/32; C07C251/34; C07C251/48; C07C255/00; C07C255/01; C07C255/32; C07C255/41; C07C255/45; C07C255/47; C07C309/00; C07C309/63; C07C309/64; C07C309/65; C07C323/00; C07C323/50; C07C323/61; C07C327/00; C07C327/20; C07C327/32; C07C45/00; C07C45/27; C07C45/28; C07C45/61; C07C45/67; C07C45/673; C07C49/00; C07C49/587; C07C49/647; C07C49/653; C07C49/687; C07C49/697; C07C65/00; C07C65/21; C07C65/28; C07C69/00; C07C69/76; C07D213/24; C07D213/54; C07D213/55; C07D277/00; C07D277/02; C07D277/20; C07D277/22; C07D277/30; C07D307/00; C07D307/02; C07D307/34; C07D307/38; C07D307/54; C07D309/00; C07D309/02; C07D309/04; C07D309/06; C07D309/08; C07D309/10; C07D309/12; C07D333/00; C07D333/02; C07D333/04; C07D333/06; C07D333/24; C07D339/00; C07D339/08; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/0803; C07F7/081; C07F7/18; C07F7/1804; C07C2602/00; C07C2602/02; C07C2602/04; C07C2602/10
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
396 words
A compound of the formula ##STR9## wherein R 1 is hydrogen or alkyl of 1 to 10 carbons; R 2 and R 3 are hydrogen, or alkyl of 1 to 6 carbons and the substituted ethynyl group occupies either the 2 or the 3 position of the tetrahydronaphthalene nucleus; m is an integer having the value of 0-3; o is an integer having the value 0-4; Y is a phenyl group, or heteroaryl selected from a group consisting of pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl, oxazolyl, and imidazolyl, said groups being optionally substituted with one or two R 2 groups; 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 , CR 7 OR 13 O, or tri-lower alkylsilyl, 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 trimethylsilylalkyl where the alkyl group has 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, and R 14 is hydrogen, alkyl of 1 to 10 carbons, alkenyl of 2 to 10 carbons and having 1 to 3 double bond, alkynyl having 2 to 10 carbons and 1 to 3 triple bonds, carbocyclic aryl selected from the group consisting of phenyl, C 1 -C 10 -alkylphenyl, naphthyl, C 1 -C 10 -alkylnaphthyl, phenyl-C 1 -C 10 alkyl, naphthyl-C 1 -C 10 alkyl, R 14 is COR 8 , or the two R 14 groups together with the N jointly form a 5 or 6 membered ring.
Claim 2
Dependent Claim
396 words
A compound of the formula ##STR9## wherein R 1 is hydrogen or alkyl of 1 to 10 carbons; R 2 and R 3 are hydrogen, or alkyl of 1 to 6 carbons and the substituted ethynyl group occupies either the 2 or the 3 position of the tetrahydronaphthalene nucleus; m is an integer having the value of 0-3; o is an integer having the value 0-4; Y is a phenyl group, or heteroaryl selected from a group consisting of pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl, oxazolyl, and imidazolyl, said groups being optionally substituted with one or two R 2 groups; 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 , CR 7 OR 13 O, or tri-lower alkylsilyl, 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 trimethylsilylalkyl where the alkyl group has 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, and R 14 is hydrogen, alkyl of 1 to 10 carbons, alkenyl of 2 to 10 carbons and having 1 to 3 double bond, alkynyl having 2 to 10 carbons and 1 to 3 triple bonds, carbocyclic aryl selected from the group consisting of phenyl, C 1 -C 10 -alkylphenyl, naphthyl, C 1 -C 10 -alkylnaphthyl, phenyl-C 1 -C 10 alkyl, naphthyl-C 1 -C 10 alkyl, R 14 is COR 8 , or the two R 14 groups together with the N jointly form a 5 or 6 membered ring.
Claim 3
Dependent Claim
13 words
A compound of claim 1 where Y is phenyl, pyridyl, thienyl or furyl.
Claim 4
Dependent Claim
9 words
A compound of claim 1 where Y is phenyl.
Claim 5
Dependent Claim
13 words
A compound of claim 3 where the phenyl ring is 1,4 (para) substituted.
Claim 6
Dependent Claim
9 words
A compound of claim 1 where Y is pyridyl.
Claim 7
Dependent Claim
17 words
A compound of claim 5 where the pyridyl ring is substituted in the 2 and 5 positions.
Claim 8
Dependent Claim
11 words
A compound of claim 1 where Y is thienyl or furyl.
Claim 9
Dependent Claim
10 words
A compound of claim 1 where R 2 is hydrogen.
Claim 10
Dependent Claim
10 words
A compound of claim 1 where R 3 is hydrogen.
Claim 11
Dependent Claim
13 words
A compound of claim 1 where R 14 is hydrogen or lower alkyl.
Claim 12
Dependent Claim
305 words
A compound of the formula ##STR10## wherein R 1 is hydrogen or alkyl of 1 to 10 carbons; R 2 and R 3 are hydrogen, or alkyl of 1 to 6 carbons and the substituted ethynyl group occupies either the 2 or the 3 position of the tetrahydronaphthalene nucleus; m is an integer having the value of 0-3; o is an integer having the value 0-4; Y is phenyl or pyridyl, said groups being optionally substituted with one or two R 2 groups; 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 , CR 7 OR 13 O, or tri-lower alkylsilyl, 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 trimethylsilylalkyl where the alkyl group has 1 to 10 carbons, or a cycloalkyl group of 5 to 10 carbons, or R 8 is phenyl or lower alkylphenyl, R 9 and R10 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, and R 14 is hydrogen, alkyl of 1 to 10 carbons, or R 14 is COR 8 .
Claim 13
Dependent Claim
305 words
A compound of the formula ##STR10## wherein R 1 is hydrogen or alkyl of 1 to 10 carbons; R 2 and R 3 are hydrogen, or alkyl of 1 to 6 carbons and the substituted ethynyl group occupies either the 2 or the 3 position of the tetrahydronaphthalene nucleus; m is an integer having the value of 0-3; o is an integer having the value 0-4; Y is phenyl or pyridyl, said groups being optionally substituted with one or two R 2 groups; 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 , CR 7 OR 13 O, or tri-lower alkylsilyl, 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 trimethylsilylalkyl where the alkyl group has 1 to 10 carbons, or a cycloalkyl group of 5 to 10 carbons, or R 8 is phenyl or lower alkylphenyl, R 9 and R10 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, and R 14 is hydrogen, alkyl of 1 to 10 carbons, or R 14 is COR 8 .
Claim 14
Dependent Claim
36 words
A compound of claim 11 where A is (CH 2 ) n where n is 0-5 and where B is COOH or a pharmaceutically acceptable salt thereof, COOR 8 , or CONR 9 R 10 .
Claim 15
Dependent Claim
41 words
A compound of claim 12 where B is COOH or a pharmaceutically acceptable salt thereof, or COOR 8 where R 8 is an alkyl group of 1 to 10 carbons or trimethylsilylalkyl where the alkyl group has 1 to 10 carbons.
Claim 16
Dependent Claim
38 words
A compound of the formula ##STR11## wherein R 8 is hydrogen, an alkyl group of 1 to 10 carbons or trimethylsilylalkyl where the alkyl group has 1 to 10 carbons, and R 14 is H or lower alkyl.
Claim 17
Dependent Claim
38 words
A compound of the formula ##STR11## wherein R 8 is hydrogen, an alkyl group of 1 to 10 carbons or trimethylsilylalkyl where the alkyl group has 1 to 10 carbons, and R 14 is H or lower alkyl.
Claim 18
Dependent Claim
21 words
A compound of claim 14 where R 14 is H and R 8 is H or C 2 H 5 .
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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) | 1999-02-05 | 1999-08-07 | 2000-02-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2003-02-05 | 2003-08-07 | 2004-02-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2007-02-05 | 2007-08-07 | 2008-02-06 | $7700.00 | Window Closed / Lapsed |