Acetylenes disubstituted with a heteroaromatic group and a tetralin group and having retinoid-like activity

• US 5,354,776 A
• Filed: 06/29/1993
• Issued: 10/11/1994
• Est. Priority Date: 03/13/1987
• Status: Expired due to Fees

• Current Assignee: Acuityads
• Original Assignee: Allergan, Inc. (Canada) (Abbvie Incorporated)
• Inventors: Chandraratna, Roshantha A. S.
• Primary Examiner(s): RICHTER, JOHANN R
• Application Number:
  US08/084,843
• Time in Patent Office: 469 Days
• Field of Search: 549/483, 549/484, 549/486, 549/487, 549/497, 514/461, 514/471
• US Class Current: 514/461
• CPC Class Codes: A61P 17/00 Drugs for dermatological disorders
• CPC Class Codes: A61P 27/02 Ophthalmic agents
• CPC Class Codes: A61P 27/14 Decongestants or antiallergics
• CPC Class Codes: A61P 29/00 Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
• CPC Class Codes: A61P 37/08 Antiallergic agents antiasthmatic agents A61P11/06; ophthalmic antiallergics A61P27/14
• CPC Class Codes: C07D 213/80 in position 3

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, --CH₂ OH or an ether 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.

Claims

1. A compound of the formula ##STR6## 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 a pharmaceutically acceptable salt, ester or amide thereof, --CH₂ OH or an ether 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.

2. The compound of claim 1 where R is hydrogen or methyl, n is 0, 1 or 2 and A is furyl.

3. The compound of claim 2 where B is --COOH or a pharmaceutically acceptable salt, ester or amide thereof.

4. A pharmaceutical composition comprising a pharmaceutically acceptable excipient and a compound of the formula ##STR7## where R is hydrogen or lower alkyl;

A is furyl;

n is 0-5; and

B is H, --COOH or a pharmaceutically acceptable salt, ester or amide thereof, --CH₂ OH or an ether 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.

5. A composition according to claim 4 having anti-psoriatic activity in a mammal.

6. 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 furyl;

n is 0-5; and

B is H, --COOH or a pharmaceutically acceptable salt, ester or amide thereof, --CH₂ OH or an ether 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.