EP0284261A1
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EP
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Acetylenes disubstituted with a heteroaromatic group and a tetralin group having retinoid like activity
Assignee: Allergan Inc
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Filing: 1988-03-11
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Granted: —
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Expires: 2008-03-11
Abstract
Abstract Retinoid-like activity is exhibited by compounds of the formula 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, -CH₂OH or an ester or ester derivative thereof, or -CHO or an acetal derivative thereof, or -COR₁ or a ketal derivative thereof where R₁ is -(CH₂) m CH₃ where m is 0-4; or a pharmaceutically acceptable salt thereof.
Inventors
- 👤 Roshantha A.S. Chandraratna
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-03 18:38
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: 12
Claim 1
Independent Claim
96 words
A process for making a compound of the formula where R is hydrogen or lower alkyl; A is pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl or pyrazinyl; n is 0-5; and B is H, a protected acid, alcohol, aldehyde or ketone; which process comprises reacting a compound of formula II with a compound of formula III in the presence of Pd(PQ₃)₄ (Q is phenyl) or a similar complex where X is halogen, preferably I; n and A are defined above; and B is H, a protected acid, alcohol, aldehyde or ketone, giving the corresponding compound of formula I.
Claim 2
Dependent Claim
96 words
A process for making a compound of the formula where R is hydrogen or lower alkyl; A is pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl or pyrazinyl; n is 0-5; and B is H, a protected acid, alcohol, aldehyde or ketone; which process comprises reacting a compound of formula II with a compound of formula III in the presence of Pd(PQ₃)₄ (Q is phenyl) or a similar complex where X is halogen, preferably I; n and A are defined above; and B is H, a protected acid, alcohol, aldehyde or ketone, giving the corresponding compound of formula I.
Claim 3
Dependent Claim
21 words
The process of claim 1 wherein R is hydrogen or methyl, n is 0, 1 or 2 and A is pyridyl.
Claim 4
Dependent Claim
11 words
The process of claim 2 wherein B is a protected acid.
Claim 5
Dependent Claim
15 words
The process of claim 3 wherein the resulting compound is ethyl 6-[2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)ethynyl]nicotinoate or ethyl 6-[2-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphth-2-yl)ethynyl]nicotinoate.
Claim 6
Dependent Claim
16 words
A process according to claim 1 where A is thienyl and B is a protected acid.
Claim 7
Dependent Claim
16 words
A process according to claim 1 where A is furyl and B is a protected acid.
Claim 8
Dependent Claim
19 words
A process according to claim 1 where A is pyridazinyl, pyrimidinyl or pyrazinyl and B is a protected acid.
Claim 9
Dependent Claim
53 words
A process for making a compound of the formula where R is hydrogen or lower alkyl; A is pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl or pyrazinyl; n is 0-5; and B is -COOH or a pharmaceutically acceptable salt, an alcohol, aldehyde or ketone which process comprises deprotecting a protected acid, alcohol, aldehyde or ketone.
Claim 10
Dependent Claim
53 words
A process for making a compound of the formula where R is hydrogen or lower alkyl; A is pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl or pyrazinyl; n is 0-5; and B is -COOH or a pharmaceutically acceptable salt, an alcohol, aldehyde or ketone which process comprises deprotecting a protected acid, alcohol, aldehyde or ketone.
Claim 11
Dependent Claim
17 words
A process of claim 8 which gives 6-[2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)ethynyl]nicotinic acid, 6-[2-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphth-2-yl)ethynyl]nicotinic acid or a pharmaceutically acceptable salt thereof.
Claim 12
Dependent Claim
36 words
A process for preparing a pharmaceutical composition containing a compound of formula I as defined in any one of claims 1 to 10 which process comprises bringing the compound into association with a pharmaceutically acceptable carrier.
References Cited (Backward Citations)
GB2130580A
Cited
EP0176034B1
Cited
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