US5675033A
Expired / Lapsed
US
⏱️ 0.0 years remaining
2,4-pentadienoic acid derivatives having retinoid-like biological activity
Assignee: IO Therapeutics Inc
•
Filing: 1995-06-06
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Granted: 1997-10-07
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Expires: 2015-06-06
Abstract
Abstract Compounds of Formula 1 <IMAGE> Formula 1 wherein Z is selected from the group consisting of the radicals shown in Formula 2 and in Formula 3, <IMAGE> Formula 2 <IMAGE> Formula 3 Y is cycloalkyl or cycloalkenyl of 3 to 8 carbons optionally substituted with one or two R4 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 R4 groups, the divalent Y radical being substituted by the Z and -CR1=CR1-CR1=CR1 groups on adjacent carbons; X is S, O, or NR5; n is 1 or 2; R1 and R2 independently are H, lower alkyl or fluoroalkyl; R3 is hydrogen, lower alkyl, Cl or Br; R4 is lower alkyl, fluoroalkyl or halogen; R5 is H or lower alkyl, and B is hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR8, CONR9R10, -CH2OH, CH2OR11, CH2OCOR11, CHO, CH(OR12)2, CHOR13O, -COR7, CR7(OR12)2, CR7OR13O, or tri-lower alkylsilyl, where R7 is an alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons, R8 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 R8 is phenyl or lower alkylphenyl, R9 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, R11 is lower alkyl, phenyl or lower alkylphenyl, R12 is lower alkyl, and R13 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 07:28
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: 17
Claim 1
Independent Claim
185 words
A compound of the formula ##STR10## wherein R 2 is hydrogen or lower alkyl; R 3 is hydrogen 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
185 words
A compound of the formula ##STR10## wherein R 2 is hydrogen or lower alkyl; R 3 is hydrogen 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
12 words
A compound in accordance with claim 1 wherein R 2 is methyl.
Claim 4
Dependent Claim
25 words
A compound in accordance with claim 2 wherein B is COOH or a pharmaceutically acceptable salt thereof, COOR 8 or CONR 9 R 10 .
Claim 5
Dependent Claim
21 words
A compound in accordance with claim 3 where the phenyl group is attached to the 2 position of the tetrahydronaphthalene nucleus.
Claim 6
Dependent Claim
21 words
A compound in accordance with claim 4 where the configuration about the double bond adjacent to the phenyl ring is trans.
Claim 7
Dependent Claim
46 words
A compound in accordance with claim 5 where the B group represents COOH, COOCH 3 or COOC 2 H 5 , R 3 is attached to the 3 position of the tetrahydronaphthalene nucleus and configuration about the double bond adjacent to the B group is trans.
Claim 8
Dependent Claim
11 words
A compound in accordance with claim 6 where B is COOH.
Claim 9
Dependent Claim
15 words
A compound in accordance with claim 6 where B is COOC 2 H 5 .
Claim 10
Dependent Claim
46 words
A compound in accordance with claim 5 where the B group represents COOH, COOCH 3 or COOC 2 H 5 , R 3 is attached to the 3 position of the tetrahydronaphthalene nucleus and configuration about the double bond adjacent to the B group is cis.
Claim 11
Dependent Claim
11 words
A compound in accordance with claim 9 where B is COOH.
Claim 12
Dependent Claim
207 words
A compound of the formula ##STR11## where 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 H, lower alkyl, fiuoroalkyl or halogen, 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 O COR 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 13
Dependent Claim
207 words
A compound of the formula ##STR11## where 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 H, lower alkyl, fiuoroalkyl or halogen, 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 O COR 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 14
Dependent Claim
78 words
A compound of the formula ##STR12## where R 4 is lower alkyl of 1 to 6 carbons; B is COOH or COOR 8 where R 8 is lower alkyl of 1 to 6 carbons, and the configuration about the cyclopropane ring is cis, and the configuration about the double bonds in the pentadienoic acid or ester chain attached to the cyclopropane ring is trans in each of said double bonds, or a pharmaceutically acceptable salt of said compound.
Claim 15
Dependent Claim
78 words
A compound of the formula ##STR12## where R 4 is lower alkyl of 1 to 6 carbons; B is COOH or COOR 8 where R 8 is lower alkyl of 1 to 6 carbons, and the configuration about the cyclopropane ring is cis, and the configuration about the double bonds in the pentadienoic acid or ester chain attached to the cyclopropane ring is trans in each of said double bonds, or a pharmaceutically acceptable salt of said compound.
Claim 16
Dependent Claim
24 words
A compound in accordance with claim 12 where B is COOH, and R 4 is methyl, or a pharmaceutically acceptable salt of said compound.
Claim 17
Dependent Claim
20 words
A compound in accordance with claim 12 where B is COOC 2 H 5 , and R 4 is methyl.
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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) | 2000-10-06 | 2001-04-07 | 2001-10-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2004-10-06 | 2005-04-07 | 2005-10-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2008-10-06 | 2009-04-07 | 2009-10-07 | $7700.00 | Window Closed / Lapsed |