1,9-Dihydroxyoctahydrophenanthrenes and intermediates therefor

Abstract

Abstract Compounds of the formula <IMAGE> <IMAGE> +TR <IMAGE> wherein R1 is hydrogen, benzyl, benzoyl, alkanoyl of 1 to 5 carbon atoms or -CO-(CH2)p-NR'R'' wherein p is 0 or an integer from 1 to 4; each of R' and R'' when taken individually is hydrogen or alkyl of 1 to 4 carbon atoms; R' and R'' when taken together with the nitrogen to which they are attached form a 5- or 6-membered heterocyclic ring selected from piperidino, pyrollo, pyrrolidino, morpholino and N-alkylpiperazino having from 1 to 4 carbon atoms in the alkyl group; R2 is selected from hydrogen, alkanoyl of 1 to 6 carbon atoms and benzoyl; R3 is selected from hydrogen, methyl and ethyl; R4 is selected from hydrogen, alkyl of 1 to 6 carbon atoms and benzyl; Z is selected from: (a) alkylene having from one to nine carbon atoms; (b) -(alk1)m-X-(alk2)n- wherein each of (alk1) and (alk2) is alkylene having from 1 to 9 carbon atoms, with the proviso that the summation of carbon atoms in (alk1) plus (alk2) is not greater than 9; m and n are each 0 or 1; X is selected from O, S, SO and SO2; and W is selected from hydrogen, methyl, pyridyl, piperidyl, phenyl, monochlorophenyl, monofluorophenyl and <IMAGE> wherein W1 is selected from hydrogen, phenyl, monochlorophenyl and monofluorophenyl; a is an integer from 1 to 5 and b is 0 or an integer from 1 to 4, with the proviso that the sum of a and b is not greater than 5. Compounds I and II are useful as analgesics. Compound III is useful as an intermediate for the preparation of Compounds I and II. Intermediates for the preparation of I, II and III are disclosed. A process for the use of compounds I and II to produce analgesia is also described.

Inventors

• 👤 Thomas H. Althuis
• 👤 Charles A. Harbert
• 👤 Michael R. Johnson
• 👤 Lawrence S. Melvin, Jr.

Bibliographic Details