Synthesis of 6‐Amino Acid Substituted Derivatives of the Highly Potent Analgesic 14‐O‐Methyloxymorphone |
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Authors: | Johannes Schü tz,Wolfgang Brandt,Mariana Spetea,Klaus Wurst,Gerhard Wunder,Helmut Schmidhammer |
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Abstract: | The novel morphinans 13 – 18 , which carry amino acid substituents at C(6), with potentially limited access to the central nervous system were prepared in two steps from 14‐O‐methyloxymorphone ( 5 ). Reductive amination with amino acid tert‐butyl esters gave compounds 7 – 12 , which were hydrolyzed with tetrafluoroboric acid. Structure elucidation (including X‐ray analysis), preliminary μ‐opioid receptor binding studies, and calculations of pharmacokinetic parameters were carried out. |
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