Aryl or heteroaryl amides of tetrahydronaphthalene, chroman, thiochroman and 1,2,3,4,-tetrahydroquinoline carboxylic acids, having an electron withdrawing substituent in the aromatic or heteroaromatic moiety, having retinoid-like biological activity

A compound of the formula ##STR13## wherein R.sub.1 is independently H or alkyl of 1 to 6 carbons;

• R.sub.2 is hydrogen, or lower alkyl of 1 to 6 carbons;
• W.sub.1, W.sub.2, W.sub.3, and W.sub.4, each is independently selected from the group consisting of H, F, Br, Cl, I, fluoro substituted C.sub.1-6 alkyl, NO.sub.2, N.sub.3, OH, OCH.sub.2 OCH.sub.3, OC.sub.1-10 alkyl and C.sub.1-6 alkyl, with the proviso that at least one of the W.sub.3, and W.sub.4 groups is not H nor C.sub.1-6 alkyl;
• X is O or S;
• Z is O or S;
• A is (CH.sub.2).sub.q where q 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, and
• B is 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, CH(OR.sub.13 O), --COR.sub.7, CR.sub.7 (OR.sub.12).sub.2, CR.sub.7 (OR.sub.13 O), where R.sub.7 is an alkyl, cycloalkyl or alkenyl group containing up to 5 carbons, R.sub.8 is an alkyl group of 1 to 10 carbons or trimethylsilylalkyl where the alkyl group has 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, phenyl or lower alkylphenyl, R.sub.12 is lower alkyl, and R.sub.13 is divalent alkyl radical of 2-5 carbons.

A compound of the formula ##STR14## wherein X is S, O;

• R.sub.1 is independently H or alkyl of 1 to 6 carbons;
• R.sub.2 is hydrogen, or lower alkyl of 1 to 6 carbons;
• R.sub.3 is hydrogen, lower alkyl of 1 to 6 carbons or F;
• m is an integer having the value of 0-2;
• o is an integer having the value of 0-4;
• r is an integer having the value 0-2;
• Y is a phenyl or naphthyl group, or heteroaryl selected from a group consisting of pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl, oxazolyl, imidazolyl and pyrrazolyl, said phenyl, naphthyl and heteroaryl groups being optionally substituted with one or two R.sub.2 groups;
• W.sub.1 is a substituent selected from the group consisting of fluoro substituted C.sub.1-6 alkyl, NO.sub.2, N.sub.3, OH, OCH.sub.2 OCH.sub.3, tetrazol, CN, SO.sub.2 C.sub.1-6 -alkyl, SO.sub.2 C.sub.1-6 -fluoro substituted alkyl, SO--C.sub.1-6 alkyl, CO--C.sub.1-6 alkyl, COOR.sub.8, phenyl, phenyl itself substituted with a W.sub.2 group other than with phenyl or substituted phenyl;
• W.sub.2 is a substituent selected from the group consisting of H, F, Br, Cl, I, C.sub.1-6 alkyl, fluoro substituted C.sub.1-6 alkyl, NO.sub.2, N.sub.3, OH, OCH.sub.2 OCH.sub.3, OC.sub.1-10 alkyl, tetrazol, CN, SO.sub.2 C.sub.1-6 -alkyl, SO.sub.2 C.sub.1-6 -fluoro substituted alkyl, SO--C.sub.1-6 alkyl, CO--C.sub.1-6 alkyl, COOR.sub.8, phenyl, phenyl itself substituted with a W.sub.2 group other than with phenyl or substituted phenyl;
• W.sub.3 is a substituent selected from the group consisting of F, Br, Cl, I, C.sub.1-6 alkyl, fluoro substituted C.sub.1-6 alkyl, NO.sub.2, N.sub.3, OH, OCH.sub.2 OCH.sub.3, OC.sub.1-10 alkyl, tetrazol, CN, SO.sub.2 C.sub.1-6 -alkyl, SO.sub.2 C.sub.1-6 -fluoro substituted alkyl, SO--C.sub.1-6 alkyl, CO--C.sub.1-6 alkyl, COOR.sub.8, phenyl, phenyl itself substituted with a W.sub.3 group other than with phenyl or substituted phenyl;
• L is --(C.dbd.Z)--NH-- or --HN--(C.dbd.Z)--
• Z is O or S;
• A is (CH.sub.2)g where q 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, and
• B is 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, CH(OR.sub.13 O), --COR.sub.7, CR.sub.7 (OR.sub.12).sub.2, CR.sub.7 (OR.sub.13 O), where R.sub.7 is an alkyl, cycloalkyl or alkenyl group containing up to 5 carbons, R.sub.8 is an alkyl group of 1 to 10 carbons or trimethylsilylalkyl where the alkyl group has 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, phenyl or lower alkylphenyl, R.sub.12 is lower alkyl, and R.sub.13 is divalent alkyl radical of 2-5 carbons.