Novel opiates and antagonists. 5. 7-Carbethoxy-N-(cycloalkylmethyl)-3-hydroxymorphinan-6-ones and -isomorphinan-6-ones.
J Med Chem
; 25(8): 986-90, 1982 Aug.
Article
em En
| MEDLINE
| ID: mdl-7120287
ABSTRACT
A direct conversion of deoxydihydrothebaine-phi (1) to 3-methoxymorphinan-6-one (3Ca) and its trans isomer 3Ta was achieved in excellent yield by the catalytic reduction of 1 in AcOH containing CF3COOH. Treatment of 3Ca or 3Ta with NaH and diethyl carbonate formed the corresponding 7-carbethoxy derivatives 4a which, on O-demethylation, furnished the 3-hydroxy compounds 4b. The analgesic N-methyl compounds 3 were converted to the 17-(cyclopropylmethyl) or 17-(cyclobutylmethyl) derivatives 6--8. Two of these compounds, one in the cis (7Ca) and the other in the trans (7Ta) series, showed mixed agonist/antagonist activity in the pentazocine range.
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01-internacional
Base de dados:
MEDLINE
Assunto principal:
Morfinanos
/
Antagonistas de Entorpecentes
/
Entorpecentes
Limite:
Animals
Idioma:
En
Ano de publicação:
1982
Tipo de documento:
Article