Acetylenes disubstituted with a 5 substituted tetrahydronaphthyl group and with an aryl or heteroaryl group having retinoid-like biological activity

US5514825A · kind A · utility

Assignee

• Allergan, Inc. · US

Inventors

• Vidyasagar Vuligonda · Irvine, US
• Min Teng · Aliso Viejo, US
• Richard L. Beard · Newport Beach, US
• Alan T. Johnson · Rancho Santa Margarita, US
• Tien T. Duong · Irvine, US
• Yuan Lin · 流花街道, CN
• Roshantha A. Chandraratna · معلمی نژاد, US

Key dates

• Filing date: Dec 29, 1994
• Grant date: May 7, 1996
• Expiry date: Dec 29, 2014

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C2602/10
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Compounds of the formula ##STR1## wherein R.sub.1 is hydrogen or alkyl of 1 to 10 carbons; R.sub.2 and R.sub.3 are hydrogen, or alkyl of 1 to 6 carbons and the substituted ethynyl group occupies either the 2 or the 3 position of the tetrahydronaphthalene nucleus; m is an integer having the value of 0-3; o is an integer having the value 0-4; Y is a phenyl group, or heteroaryl selected from a group consisting of pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl, oxazolyl, and imidazolyl, said groups being optionally substituted with one or two R.sub.2 groups; A is (CH.sub.2).sub.n where n is 0-5, lower branched chain alkyl having 3-6 carbons, cycloalkyl having 3-6 carbons, alkenyl having 2-6 carbons and 1 or 2 double bonds, alkynyl having 2-6 carbons and 1 or 2 triple bonds; B is hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR.sub.8, CONR.sub.9 R.sub.10, --CH.sub.2 OH, CH.sub.2 OR.sub.11, CH.sub.2 OCOR.sub.11, CHO, CH(OR.sub.12).sub.2, CHOR.sub.13 O, --COR.sub.7, CR.sub.7 (OR.sub.12).sub.2, CR.sub.7 OR.sub.13 O, or tri-lower alkylsilyl, where R.sub.7 is an alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons, R.sub.8 is an alkyl group …