1,9-dihydroxyoctahydrophenanthrenes and intermediates therefor

Details 1,9-dihydroxyoctahydrophenanthrenes and intermediates therefor 1,9-dihydroxyoctahydrophenanthrenes and intermediates therefor

C - Chemistry, Metallurgy

07

C

260/292, 260/295

C07C 43/20 (2006.01) C07C 41/22 (2006.01) C07C 41/26 (2006.01) C07C 43/225 (2006.01) C07C 43/23 (2006.01) C07C 45/45 (2006.01) C07C 45/46 (2006.01) C07C 45/54 (2006.01) C07C 45/59 (2006.01) C07C 45/61 (2006.01) C07C 45/67 (2006.01) C07C 45/68 (2006.01) C07C 45/71 (2006.01) C07C 45/73 (2006.01) C07C 49/747 (2006.01) C07C 49/755 (2006.01) C07C 49/757 (2006.01) C07C 49/83 (2006.01) C07C 49/84 (2006.01) C07D 211/32 (2006.01) C07D 213/30 (2006.01) C07D 213/50 (2006.01) C07D 295/14 (2006.01) C07D 317/22 (2006.01)

Patent

CA 1097668

Abstract Tbe disclosed invention relates to a process for preparing novel 3,6-substltuted-1,9-dihydroxyoctahydrophenanthrenes and 3,6-substituted-1-hydroxyoctahydrophenanthren-9-ones and derivatives thereof comprising the reduction of the corresponding 3,6-substituted-hexahydrophenanthren-9-one. The compounds so formed are useful as analgesic agents which are non-narcotic and free of addiction liability. The compounds are also useful as antihypertensive, immunosuppressant, tranquilizing, diuretic and anti-anxiety agents and as agents for the treatment of glaucoma. Preferred compounds made by this process include trans-6a,10a-1-hydxoxy-3-(5'-phenyl-2'-pentyloxy)-6,6-dimethyl- 5,6,6a,7,8,9,10,10a-octahydrophenanthren-9-.beta.-ol, trans-6a-,10a- l-hydxoxy-3-(5'-phenyl-2'-pentyloxy)-6,6-dimethyl-5,5,6a,7,8,9, 10,10a-octahydrophenanthren-9-one, 1-hydroxy-3-(5'-phenyl-2'- pentyloxyl-5,6,6a,7,8,9,10,10a-octahydrophenanthren-9-ol and l-hydroxy-3-(5'-phenyl-2'-pentyloxy)-5,6,6a,7,8,9,10,10a- octahydrophenanthren-9-one. Also disclosed are processes for the preparation of novel intermediates useful for the preparation of the above analgesic agents, especially 3,6,8-substituted-2- hydroxymethylene-1-tetralones and 3,6,8-substituted-1-tetralones.

314035

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