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Synthesis of the metabolites of oxapadol, a new non‐narcotic analgesic agent
Author(s) -
Guerret Patrick,
Ancher JeanFrançois,
Langlois Michel
Publication year - 1983
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570200618
Subject(s) - chemistry , dioxolane , moiety , hydrolysis , hydroxymethyl , analgesic , organic chemistry , glycerol , carboxylic acid , narcotic antagonists , medicinal chemistry , biochemistry , pharmacology , medicine , (+) naloxone , receptor , opioid
Abstract Different metabolites (2‐7) of oxapadol 1 were carried out from 3 by known methods. Their acidic hydrolysis provided compounds 4 in which the dioxolane moiety was opened. The reaction of glycerol with compounds 3 gave the dioxolane derivatives 5 which have a hydroxymethyl group and which (R = H) gave by oxidation the carboxylic acid 7. From 3 (R = H), the hydroxy acid 6 has been also prepared.