Disubstituted aryl and heteroaryl imines having retinoid-like biological activity

US5498755A · kind A · utility

Inventors

• Roshantha A. Chandraratna · معلمی نژاد, US
• Min Teng · Aliso Viejo, US

Key dates

• Filing date: Aug 23, 1994
• Grant date: Mar 12, 1996
• Expiry date: Aug 23, 2014

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D311/58
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Compounds of the formula ##STR1## wherein the R.sub.1 groups independently are hydrogen, lower alkyl, or two geminal R.sub.1 groups jointly represent an oxo (.dbd.O) or a thio (.dbd.S) group; R.sub.2 is hydrogen or lower alkyl, or halogen; M is or --N.dbd.CR.sub.4 -- or --R.sub.4 C.dbd.N-- where R.sub.4 is hydrogen or lower alkyl; X is C(R.sub.1).sub.2 ; Y is phenyl optionally substituted with an R.sub.3 group which is lower alkyl or halogen; A is (CH.sub.2).sub.n where n is 0-5, lower branched chain alkyl, cycloalkyl, alkenyl, alkynyl; 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.2OR.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, or CR.sub.7 OR.sub.13 O, where R.sub.7 is an alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons, R.sub.8 is an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5 to 10 carbons, or R.sub.8 is phenyl or lower alkylphenyl, R.sub.9 and R.sub.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.sub.11 is lower alkyl, p…