US5817836A
Expired / Lapsed
US
⏱️ 0.0 years remaining
2,4-pentadienoic acid derivatives having retinoid-like biological activity
Assignee: Allergan Inc
•
Filing: 1997-05-12
•
Granted: 1998-10-06
•
Expires: 2017-05-12
Abstract
Abstract Compounds of Formula 1 ##STR1## wherein Z is selected from the group consisting of the radicals shown in Formula 2 and in Formula 3, ##STR2## Y is cycloalkyl or cycloalkenyl of 3 to 8 carbons optionally substituted with one or two R 4 groups, or Y is selected from phenyl, pyridyl, thienyl, furyl, pyrrolyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl, oxazolyl, and imidazolyl, said groups being optionally substituted with one or two R 4 groups, the divalent Y radical being substituted by the Z and --CR 1 ═CR 1 --CR 1 ═CR 1 groups on adjacent carbons; X is S, O, or NR 5 ; n is 1 or 2; R 1 and R 2 independently are H, lower alkyl or fluoroalkyl; R 3 is hydrogen, lower alkyl, Cl or Br; R 4 is lower alkyl, fluoroalkyl or halogen; R 5 is H or lower alkyl, and 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, a cycloalkyl group of 5 to 10 carbons or trimethylsilylalkyl where the alkyl group has 1 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
- 👤 Vidyasagar Vuligonda
- 👤 Roshantha A. Chandraratna
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 16:11
CPC Classifications
C; C07; C07D; C07D333/00; C07D333/50; C07D333/52; C07D333/54; A; A61; A61K; A61K31/00; A61K31/185; A61K31/19; A61K31/20; A61K31/21; A61K31/215; A61K31/22; A61K31/23; A61P; A61P17/00; A61P43/00; C07C; C07C57/00; C07C57/46; C07C57/50; C07C69/00; C07C69/612; C07C69/618; C07D311/00; C07D311/02; C07D311/04; C07D311/58; C07D335/00; C07D335/04; C07D335/06
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
286 words
A compound of Formula 1 ##STR12## wherein Z is selected from the group consisting of the radicals a radical shown in Formula 2 and in Formula 3, ##STR13## Y is selected from pyridyl, pyrrolyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl, oxazolyl, and imidazolyl, said groups being optionally substituted with one or two R 4 groups, the divalent Y radical being substituted by the Z and --CR 1 ═CR 1 --CR 1 ═CR 1 )-- groups on adjacent carbons; X is NR 5 ; n is 1 or 2; R 1 and R 2 independently are H, lower alkyl or fluoroalkyl; R 3 is hydrogen, lower alkyl, Cl or Br; R 4 is lower alkyl, fluoroalkyl or halogen; R 5 is H or lower alkyl, and 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, a cycloalkyl group of 5 to 10 carbons or trimethylsilylalkyl where the alkyl group has 1 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
286 words
A compound of Formula 1 ##STR12## wherein Z is selected from the group consisting of the radicals a radical shown in Formula 2 and in Formula 3, ##STR13## Y is selected from pyridyl, pyrrolyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl, oxazolyl, and imidazolyl, said groups being optionally substituted with one or two R 4 groups, the divalent Y radical being substituted by the Z and --CR 1 ═CR 1 --CR 1 ═CR 1 )-- groups on adjacent carbons; X is NR 5 ; n is 1 or 2; R 1 and R 2 independently are H, lower alkyl or fluoroalkyl; R 3 is hydrogen, lower alkyl, Cl or Br; R 4 is lower alkyl, fluoroalkyl or halogen; R 5 is H or lower alkyl, and 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, a cycloalkyl group of 5 to 10 carbons or trimethylsilylalkyl where the alkyl group has 1 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
17 words
A compound in accordance with claim 1 where Y is selected from the group consisting of pyridyl.
Claim 4
Dependent Claim
16 words
A compound in accordance with claim 1 where Z is the radical shown in Formula 2.
Claim 5
Dependent Claim
16 words
A compound in accordance with claim 1 where Z is the radical shown in Formula 3.
Claim 6
Dependent Claim
26 words
A compound in accordance with claim 1 where B is COOH or a pharmaceutically acceptable salt thereof, COOR 8 , or CONR 9 R 10 .
Claim 7
Dependent Claim
14 words
A compound in accordance with claim 1 where R 1 is H or methyl.
Claim 8
Dependent Claim
20 words
A compound in accordance with claim 1 where Z is the radical shown in Formula 2 and n is 2.
Claim 9
Dependent Claim
22 words
A compound in accordance with claim 1 where Z is the radical shown in Formula 3 and X is S or O.
Claim 10
Dependent Claim
264 words
A compound of Formula 1 ##STR14## wherein Z is the group shown in the formula, ##STR15## Y is thienyl or furyl, said thienyl or furyl groups being optionally substituted with one or two R 4 groups, the divalent Y radical being substituted by the Z and --CR 1 ═CR 1 --CR 1 ═CR 1 )-- groups on adjacent carbons; X is NR 5 ; R 1 and R 2 independently are H, lower alkyl or fluoroalkyl; R 3 is hydrogen, lower alkyl, Cl or Br; R 4 is lower alkyl, fluoroalkyl or halogen; R 4 is H or lower alkyl, and 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, a cycloalkyl group of 5 to 10 carbons or trimethylsilylalkyl where the alkyl group has 1 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 11
Dependent Claim
264 words
A compound of Formula 1 ##STR14## wherein Z is the group shown in the formula, ##STR15## Y is thienyl or furyl, said thienyl or furyl groups being optionally substituted with one or two R 4 groups, the divalent Y radical being substituted by the Z and --CR 1 ═CR 1 --CR 1 ═CR 1 )-- groups on adjacent carbons; X is NR 5 ; R 1 and R 2 independently are H, lower alkyl or fluoroalkyl; R 3 is hydrogen, lower alkyl, Cl or Br; R 4 is lower alkyl, fluoroalkyl or halogen; R 4 is H or lower alkyl, and 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, a cycloalkyl group of 5 to 10 carbons or trimethylsilylalkyl where the alkyl group has 1 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 12
Dependent Claim
11 words
A compound in accordance with claim 9 where Y is thienyl.
Claim 13
Dependent Claim
26 words
A compound in accordance with claim 10 where B is COOH or a pharmaceutically acceptable salt thereof, COOR 8 , or CONR 9 R 10 .
Claim 14
Dependent Claim
11 words
A compound in accordance with claim 9 where Y is furyl.
Claim 15
Dependent Claim
26 words
A compound in accordance with claim 12 where B is COOH or a pharmaceutically acceptable salt thereof, COOR 8 , or CONR 9 R 10 .
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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) | 2001-10-05 | 2002-04-06 | 2002-10-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2005-10-05 | 2006-04-06 | 2006-10-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2009-10-05 | 2010-04-06 | 2010-10-06 | $7700.00 | Window Closed / Lapsed |