Oxime substituted tetrahydronaphthalene derivatives having retinoid and/or retinoid antagonist-like biological activity

A compound of the formula ##STR29## wherein X.sub.1 is ›C(R.sub.1).sub.2 !.sub.n where R.sub.1 is independently H or alkyl of 1 to 6 carbons, and n is an integer between 0 and 2;

• Z is
• --N.dbd.N--,
• --N(O).dbd.N--,
• --N.dbd.N(O)--,
• --N.dbd.CR.sub.1 --,
• --CR.sub.1 .dbd.N--;
• --(CR.sub.1 .dbd.CR.sub.1).sub.n' -- where n' is an integer having the value 0-5,
• --CO--NR.sub.1 --,
• --CS--NR.sub.1 --,
• --NR.sub.1 --CO,
• --NR.sub.1 --CS,
• --COO--,
• --OCO--;
• --CSO--;
• --OCS--;
• --CO--CR.sub.1 .dbd.CR.sub.1 --;
• R.sub.2 is hydrogen, lower alkyl of 1 to 6 carbons, F, Cl, Br, I, CF.sub.3, fluoro substituted alkyl of 1 to 6 carbons, OH, SH, alkoxy of 1 to 6 carbons, or alkylthio 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 0-3;
• o is an integer having the value of 0-4;
• 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 and heteroaryl groups being unsubstituted substituted with one or two R.sub.2 groups, or
• when Z is --(CR.sub.1 .dbd.CR.sub.1).sub.n' -- and n' is 3, 4 or 5 then Y represents a direct valence bond between said (CR.sub.2 .dbd.CR.sub.2).sub.n' group and B;
• 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;
• 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 Si(C.sub.1-6 alkyl).sub.3, 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 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, and
• Z.sub.2 is OR.sub.1 or OR.sub.18 where R.sub.18 is phenyl, benzyl, lower alkyl or lower alkoxy substituted phenyl, or Z.sub.2 is OSi(R.sub.2).sub.3, OCOR.sub.14, OC(R.sub.15)(R.sub.16)X.sub.2 R.sub.17, N(R.sub.14).sub.2, NHCON(R.sub.14).sub.2, NHCSN(R.sub.14).sub.2, where X.sub.2 is O or S;
• R.sub.14 is hydrogen, alkyl of 1 to 10 carbons, alkenyl of 2 to 10 carbons and having 1 to 3 double bonds, alkynyl having 2 to 10 carbons and 1 to 3 triple bonds, carbocyclic aryl selected from the group consisting of phenyl, C.sub.1 -C.sub.10 -alkylphenyl, naphthyl, C.sub.1 -C.sub.10 -alkylnaphthyl, phenyl-C.sub.1 -C.sub.10 alkyl, naphthyl-C.sub.1 -C.sub.10 alkyl;
• R.sub.15 and R.sub.16 are hydrogen or lower alkyl of 1 to 6 carbons, R.sub.17 is lower alkyl of 1 to 6 carbons, or R.sub.16 and R.sub.17 jointly form a ring having a total of 4 to 5 carbons and the X.sub.2 heteroatom.