Tetrahydronaphthyl and cyclopropyl substituted 1,3-butadienes having retinoid-like activity

Abstract

Abstract Compounds of the formula ##STR1## wherein m is 1-4; R 1 -R 4 independently are hydrogen, lower alkyl of 1 to 6 carbons, Cl, Br, or I; R 5 is hydrogen, lower alkyl of 1 to 6 carbons, Cl, Br, I, lower alkoxy or lower thioalkoxy of 1-6 carbons; R 6 is hydrogen, lower alkyl, Cl, Br, I, OR 11 , SR 11 , OCOR 11 , SCOR 11 , NH2, NHR 11 , N(R 11 ) 2 , NHCOR 11 OR NR 11 --COR 11 ; R 20 is independently hydrogen or lower alkyl; A is (CH 2 ) 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 8 , CONR 9 R 10 , --CH 2 OH, CH 2 OR 11 , CH 2 OCOR 11 , CHO, CH(OR 12 ) 2 , CHOR 13 O, --COR 7 , CR 7 (OR 12 ) 2 , or CR 7 OR 13 O, where R 7 is an alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons, R 8 is an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5 to 10 carbons, or R 8 is phenyl or lower alkylphenyl, R 9 and R 10 independently are hydrogen, an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5-10 carbons, or phenyl or lower aklylphenyl, R 11 is lower alkyl, phenyl or lower alkylphenyl, R 12 is lower alkyl, and R 13 is divalent alkyl radical of 2-5 carbons, have retinoid-like activity.

Inventors

• 👤 Roshantha A. Chandraratna

Bibliographic Details