Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal
Patent
1973-06-14
1976-02-03
Winters, Sherman D.
Chemistry of carbon compounds
Miscellaneous organic carbon compounds
C-metal
C07D22126
Patent
active
039364623
ABSTRACT:
1,2,3,4,5,6-Hexahydro-1-oxo-3-(hydrocarbon or substituted hydrocarbon)-8-(H or OH)-6-(H or alkyl)-11-(H or alkyl)-2,6-methano-3-benzazocines and 1-hydroxy secondary and tertiary alcohols obtainable therefrom by reduction and by Grignard reactions, and esters of the same, are useful as central nervous system depressants, particularly as analgesics and as analgesic antagonists. The 3-substituent is introduced by alkylation, directly or by N-acylation followed by reduction of the resulting amides, of the corresponding >NH compounds either before or after introduction of the 1-oxo group into the compounds having two hydrogens at the 1-position by chromium (VI) oxidation. Various intermediates and derivatives are also descibed, including 3a,4,5,9b-tetrahydro-3,5-ethanonaphth[2,1-d]oxazol-2(3H)-ones obtained by interacting 1,2,3,4,5,6-hexahydro-1-hydroxy-2,6-methano-3-benzazocines with phosgene or by heating 1,2,3,4,5,6-hexahydro-1-hydroxy-3-carbalkoxy-2,6-methano-3-benzazocines with alkoxide ion.
REFERENCES:
patent: 3634433 (1972-01-01), Moriyama et al.
patent: 3639407 (1972-02-01), Clarke et al.
Miller Theodore C.
Sterling Drug Inc.
Winters Sherman D.
Wyatt B. Woodrow
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