US5149705A
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US
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Acetylenes disubstituted with a heteroaromatic group and a tetralin group and having retinoid like activity
Assignee: Allergan Inc
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Filing: 1987-03-13
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Granted: 1992-09-22
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Expires: 2007-03-13
Abstract
Abstract Retinoid-like activity is exhibited by compounds of the formula ##STR1## where R is hydrogen or lower alkyl; A is pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl or pyrazinyl; n is 0-5; and B is H, --COOH or an ester or amide thereof, --CH 2 OH or an ether or ester derivative thereof, or --CHO or an acetal derivative thereof, or --COR 1 or a ketal derivative thereof where R 1 is --(CH 2 ) m CH 3 where m is 0-4; or a pharmaceutically acceptable salt thereof.
Inventors
- 👤 Roshantha A. S. Chandraratna
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 06:47
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/06; C07D213/60; C07D213/78; C07D213/79; C07D213/80; A; A61; A61P; A61P17/00; A61P27/00; A61P27/02; A61P27/14; A61P29/00; A61P37/00; A61P37/08
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
165 words
A compound of the formula ##STR6## where R is hydrogen or lower alkyl; A is pyridyl; n is 0-5; and B is H, -COOH or a pharmaceutically acceptable salt, ester of saturated aliphatic alcohols of ten or fewer carbon atoms, or the cyclic or saturated aliphatic cyclic alcohols of 5 to 10 carbon atoms, or phenol, or amide or mono- or disubstituted amide of saturated aliphatic alcohols of ten or fewer carbon atoms, or the cyclic or saturated aliphatic cyclic radicals of 5 to 10 carbon atoms thereof, --CH 2 OH or a lower alkyl ether or ester of saturated aliphatic acids of ten or fewer carbon atoms or the cyclic or saturated aliphatic cyclic acids of 5 to 10 carbon atoms, or benzoic acid thereof, or --CHO or a lower alkyl acetal derivative thereof, or --COR 1 or a lower alkyl ketal derivative thereof where R 1 is --(CH 2 ) m CH 3 where m is 0-4; or a pharmaceutically acceptable salt thereof.
Claim 2
Dependent Claim
165 words
A compound of the formula ##STR6## where R is hydrogen or lower alkyl; A is pyridyl; n is 0-5; and B is H, -COOH or a pharmaceutically acceptable salt, ester of saturated aliphatic alcohols of ten or fewer carbon atoms, or the cyclic or saturated aliphatic cyclic alcohols of 5 to 10 carbon atoms, or phenol, or amide or mono- or disubstituted amide of saturated aliphatic alcohols of ten or fewer carbon atoms, or the cyclic or saturated aliphatic cyclic radicals of 5 to 10 carbon atoms thereof, --CH 2 OH or a lower alkyl ether or ester of saturated aliphatic acids of ten or fewer carbon atoms or the cyclic or saturated aliphatic cyclic acids of 5 to 10 carbon atoms, or benzoic acid thereof, or --CHO or a lower alkyl acetal derivative thereof, or --COR 1 or a lower alkyl ketal derivative thereof where R 1 is --(CH 2 ) m CH 3 where m is 0-4; or a pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim
18 words
The compound of claim 1 where R is hydrogen or methyl and n is 0, 1 or 2.
Claim 4
Dependent Claim
18 words
The compound of claim 2 wherein B is --COOH or a pharmaceutically acceptable salt, ester or amide thereof.
Claim 5
Dependent Claim
9 words
A compound of claim 3 which is ethyl 6-[2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)ethynyl]nicotionate.
Claim 6
Dependent Claim
15 words
A compound of claim 3 which is 6-[2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)ethynyl]nicotinic acid or a pharmaceutically acceptable salt thereof.
Claim 7
Dependent Claim
174 words
A pharmaceutical composition comprising a pharmaceutically acceptable excipient and a compound of the formula ##STR7## where R is hydrogen or lower alkyl; A is pyridyl; n is 0-5; and B is H, --COOH or a pharmaceutically acceptable salt, ester of saturated aliphatic alcohols of ten or fewer carbon atoms, or the cyclic or saturated aliphatic cyclic alcohols of 5 to 10 carbon atoms, or phenol, or amid or mono- or disubstituted amide of saturated aliphatic alcohols of ten or fewer carbon atoms, or the cyclic or saturated aliphatic cyclic radicals of 5 to 10 carbon atoms thereof, --CH 2 OH or a lower alkyl ether or ester of saturated aliphatic acids of ten or fewer carbon atoms or the cyclic or saturated aliphatic cyclic acids of 5 to 10 carbon atoms, or benzoic acid thereof, or --CHO or a lower alkyl acetal derivative thereof, or --COR 1 or a lower alkyl ketal derivative thereof where R 1 is --(CH 2 ) m CH 3 where m is 0-4; or a pharmaceutically acceptable salt thereof.
Claim 8
Dependent Claim
174 words
A pharmaceutical composition comprising a pharmaceutically acceptable excipient and a compound of the formula ##STR7## where R is hydrogen or lower alkyl; A is pyridyl; n is 0-5; and B is H, --COOH or a pharmaceutically acceptable salt, ester of saturated aliphatic alcohols of ten or fewer carbon atoms, or the cyclic or saturated aliphatic cyclic alcohols of 5 to 10 carbon atoms, or phenol, or amid or mono- or disubstituted amide of saturated aliphatic alcohols of ten or fewer carbon atoms, or the cyclic or saturated aliphatic cyclic radicals of 5 to 10 carbon atoms thereof, --CH 2 OH or a lower alkyl ether or ester of saturated aliphatic acids of ten or fewer carbon atoms or the cyclic or saturated aliphatic cyclic acids of 5 to 10 carbon atoms, or benzoic acid thereof, or --CHO or a lower alkyl acetal derivative thereof, or --COR 1 or a lower alkyl ketal derivative thereof where R 1 is --(CH 2 ) m CH 3 where m is 0-4; or a pharmaceutically acceptable salt thereof.
Claim 9
Dependent Claim
12 words
A composition according to claim 6 having anti-psoriatic activity in a mammal.
Claim 10
Independent Claim
190 words
A method for treating psoriasis in a mammal which method comprises administering alone or in conjunction with a pharmaceutically acceptable excipient, a therapeutically effective amount of a compound of the formula ##STR8## where R is hydrogen or lower alkyl; A is pyridyl; n is 0-5; and B is H, --COOH or a pharmaceutically acceptable salt, ester of saturated aliphatic alcohols of ten or fewer carbon atoms, or the cyclic or saturated aliphatic cyclic alcohols of 5 to 10 carbon atoms, or phenol, or amide or mono- or disubstituted amide of saturated aliphatic alcohols of ten or fewer carbon atoms, or the cyclic or saturated aliphatic cyclic radicals of 5 to 10 carbon atoms thereof, --CH 2 OH or a lower alkyl ether or ester of saturated aliphatic acids of ten or fewer carbon atoms or the cyclic or saturated aliphatic cyclic acids of 5 to 10 carbon atoms, or benzoic acid thereof, or --CHO or a lower alkyl acetal derivative thereof, or --COR 1 or a lower alkyl ketal derivative thereof where R 1 is --(CH 2 ) m CH 3 where is 0-4; or a pharmaceutically acceptable salt thereof.
Claim 11
Independent Claim
190 words
A method for treating psoriasis in a mammal which method comprises administering alone or in conjunction with a pharmaceutically acceptable excipient, a therapeutically effective amount of a compound of the formula ##STR8## where R is hydrogen or lower alkyl; A is pyridyl; n is 0-5; and B is H, --COOH or a pharmaceutically acceptable salt, ester of saturated aliphatic alcohols of ten or fewer carbon atoms, or the cyclic or saturated aliphatic cyclic alcohols of 5 to 10 carbon atoms, or phenol, or amide or mono- or disubstituted amide of saturated aliphatic alcohols of ten or fewer carbon atoms, or the cyclic or saturated aliphatic cyclic radicals of 5 to 10 carbon atoms thereof, --CH 2 OH or a lower alkyl ether or ester of saturated aliphatic acids of ten or fewer carbon atoms or the cyclic or saturated aliphatic cyclic acids of 5 to 10 carbon atoms, or benzoic acid thereof, or --CHO or a lower alkyl acetal derivative thereof, or --COR 1 or a lower alkyl ketal derivative thereof where R 1 is --(CH 2 ) m CH 3 where is 0-4; or a pharmaceutically acceptable salt thereof.
References Cited (Backward Citations)
US4269848A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1995-09-22 | 1996-03-23 | 1996-09-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1999-09-22 | 2000-03-23 | 2000-09-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2003-09-22 | 2004-03-23 | 2004-09-22 | $7700.00 | Window Closed / Lapsed |