Sri International

Leland Stanford Junior University

Gilda H Loew

John A Lawson

Joseph I DeGraw

Howard L Johnson

Joseph I De Graw

Donald A Berkowitz

Stereoisomerically pure forms of normorphine analogs which have superior analgesic and nonaddicting qualities are described. In addition, a method of separating diastereomeric forms of N-sec-alkyl-substituted analogs utilizes the hydrocarbyl(1-8C) diesters of the normorphine derivatives. A new method for preparing the N-methylalkylmethyl derivatives of normorphine and norcodeine and their conventional analogs is also disclosed. This method employs the corresponding methyl alkyl ketones and a reducing agent.

Orally active nonaddicting analgesics

Novel N-sec-alkyl derivatives of norcodeine and normorphine wherein the sec-alkyl group contains either four or five carbon atoms. Specifically included are those derivatives of norcodeine and normorphine wherein the sec-alkyl group is 2-butyl, 3-pentyl, .alpha.-methylallyl and .alpha.-methylcyclopropylmethyl. The normorphine derivatives having strong agonist potency combined with strong antagonist qualities and indicated low addiction potential. The norcodeine analogs are useful as intermediates in preparing the corresponding normorphine compounds.

N-Sec-alkyl analogs of norcodeine and normorphine and analgesic

Novel N-sec-alkyl derivatives of norcodeine and normorphine wherein the sec-alkyl group contains either four or five carbon atoms. Specifically included are those derivatives of norcodeine and normorphine wherein the sec-alkyl group is 2-butyl, 3-pentyl, .alpha.-methylallyl and .alpha.-methylcyclopropylmethyl. The normorphine derivatives have strong agonist potency combined with strong antagonist qualities and indicated low addiction potential. The norcodeine analogs are useful as intermediates in preparing the corresponding normorphine compounds.

Growing community of inventors

Atherton, CA, United States of America

Gilda H Loew