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filingDate 1982-08-17-04:00^^<http://www.w3.org/2001/XMLSchema#date>
inventor http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_f20c16dbd9c7b3742f3e00d8ffeef004
publicationDate 1983-04-29-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber FR-2515184-A1
titleOfInvention SYNTHESES OF CODEINE DERIVATIVES AND OTHER 3-O-ALKYLMORPHINS AND INTERMEDIATE COMPOUNDS USED THEREOF
abstract THE INVENTION CONCERNS THE SYNTHESIS OF DERIVATIVES OF CODEINE AND OTHER 3-0-ALKYLMORPHINES. A 14-OH GROUP IS INTRODUCED INTO A MORPHINANE BY REACTION OF SINGLE OXYGEN WITH A NEW DIENOL-ESTER OF A N-SUBSTITUENT-3-O-ALKYLNORMORPHINONE. THE COMPOUND OBTAINED IS ALSO A NEW COMPOUND WHICH CAN BE TRANSFORMED INTO NOROXYMORPHONE BY SUCCESSIVE OPERATIONS OF CATALYTIC HYDROGENATION, HYDROLYTIC REMOVAL OF THE SUBSTITUTE OF NITROGEN AND HYDROLYSIS AND O-DEALKYLATION. THE INTERMEDIATE DIENOL ESTER IS PREPARED BY N-DEMETHYLATION OF CODEINE OR ANOTHER 3-O-ALKYLMORPHINE FOLLOWED BY OXIDATION AND ESTERIFICATION OF THE OXIDIZED PRODUCT WITH AN ANHYDRIDE OR AN ACID HALOGENIDE . 14-HYDROXYMORPHINANS ARE STRONG ANALGESICS AND ANTAGONISTS OF NARCOTICS.
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