METHOD OF PRODUCING DERIVATIVES OF 4-(2-OXY-4-SUBSTITUTED)PHENYLNAPHTHALENE-2-OLES

Compounds having the formulawherein A when taken individually is hydrogen; B when taken individually is hydroxy or alkanoyloxy having from one to five carbon atoms;A and B when taken together are oxo;R, is hydrogen, benzyl, or R1' wherein R1' is alkanoyl having from one to five carbon atoms, P(O) (OH)2 and mono-and disodium and potassium salts thereof, -CO(CH2)2COOH and the sodium and potassium salts thereof, or -CO(CH2)pNR4R5 wherein p is 0 or an integer from 1 to 4, each of R4 and R5 when taken individually is hydrogen or alkyl having from one to four carbon atoms; R4 and R5 when taken together with the nitrogen to which they are attached are piperidino, pyrrolo, pyrrolidino, morpholino or N-alkylpiperazino having from one to four carbon atoms in the alkyl group;R2 when taken individually is hydrogen;R3 when taken individually is hydrogen, methyl, hydroxy, hydroxymethyl, -OR,' or -CH2OR1'; R2 and R3 when taken together are oxo, methylene or alkylenedioxy having from two to four carbon atoms;W is hydrogen, pyridyl, orwherein W, is hydrogen, chloro or fluoro;when W is hydrogen, Z is(a) alkylene having from five to thirteen carbon atoms; or(b) -lalk1)m-O-(alk2)n- wherein each of (alk,) and (alk2) is alkylene having from one to thirteen carbon atoms; each of m and n is 0 or 1; with the provisos that the summation of carbon atoms in (alk1) plus (alk2) is not less than five or greater than thirteen; and at least one of m and n is 1; when W is other than hydrogen, Z is(a) alkylene having from three to eight carbon atoms; or(b) -(elk1)m-O-(alk2)n- wherein each of (alk1) and (alk2) is alkylene having from one to eight carbon atoms; each of m and n is 0 or 1; with the provisos that the summation of carbon atoms in (alk,) plus (alk2) is not less than three or greater than eight; and at least one of m and n is 1;or a pharmaceutically acceptable acid addition salt of those compounds wherein R, is -CO(CH2)pNR4R5 and/or W is pyridyl; pharmaceutical compositions containing them, and processes for their preparation. The compounds are particularly useful in the treatment of nausea and as analgesics.