Retinoid-like compounds

US5618839A · kind A · utility

Assignee

• Bristol-Myers Squibb Company · US

Inventors

• John E. Starrett, Jr. · Middletown, US
• Kuo-Long Yu · Hamden, US
• Muzammil M. Mansuri · Lexington, US
• David R. Tortolani · Skillman, US
• Peter R. Reczek · East Amherst, US

Key dates

• Filing date: May 2, 1996
• Grant date: Apr 8, 1997
• Expiry date: May 2, 2016

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C2603/24
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The present invention relates to a compound of formula I ##STR1## or a nontoxic pharmaceutically acceptable salt, physiologically hydrolyzable ester or solvate thereof, in which PA1 X is --O--CO--, --NH--CO--, --CS--NH--, --CO--O--, --CO--NH--, --COS--, --SCO--, --SCH.sub.2 --, --CH.sub.2 --CH.sub.2 --, --C.tbd.C--, --CH.sub.2 --NH--, --COCH.sub.2 --, --NHCS--, --CH.sub.2 S--, --CH.sub.2 O--, --OCH.sub.2 --, --NHCH.sub.2 -- or --CR.sup.5 .dbd.CR.sup.6 --; PA1 R.sup.m and R.sup.k are independently hydrogen, halogen, C.sub.1-6 alkyl, hydroxy, C.sub.1-6 alkyloxy or nitro; PA1 n is zero or one; PA1 R.sup.4 is --(CH.sub.2).sub.t --Y, C.sub.1-6 alkyl, or C.sub.3-6 cycloalkyl; PA1 R.sup.1 is --CO.sub.2 Z, C.sub.1-6 alkyl, CH.sub.2 OH, --CONHR.sup.y, or CHO; PA1 R.sup.2 and R.sup.3 are independently hydrogen or C.sub.1-6 alkyl; PA1 R.sup.a and R.sup.b are independently hydrogen or C.sub.1-6 alkyl; but when n is one, R.sup.a and R.sup.b together can form a radical of the formula ##STR2## Y is naphthyl or phenyl, both radicals can be optionally substituted with one to three same or different C.sub.1-6 alkyl or halogen; PA1 Z is hydrogen or C.sub.1-6 alkyl; PA1 R.sup.5, R.sup.6 and R.sup.y ar…