Patent ID: 6642366
Filing Date: 2003-11-04
Classification: C07H

Abstract:
A process for the production of compounds of the general structure of Formula 1: in which:R1=alkyl both branched and unbranched, aryl, allyl or acyl; R2=glycoside ester; R3=alkyl, aryl, hydrogen or (CH2)nX, where n is an integer and X=NRR4, where R and R4 are hydrogen, alkyl, aryl or acyl; and in which the C(7)-C(8) linkage is olefin, dihydro, dihydroxy, hydroxyhalo, epoxy, dihalo, hydrohalo, hydrohydroxy, or olefin adducts CHX-CHY, where X and Y are epoxy, halogen or hydrohalogen; comprising conjugating 1-iodoglucuronate ester or a substituted 1-iodoglucuronate ester with morphine or substituted morphine in the presence of iodine or an iodonium compound; said substituted 1-iodoglucuronate ester having the general structure shown in Formula 2: â€ƒin which: R1=alkyl or aryl; R2=acyl, silyl, alkyl, benzyl or aryl; X=iodine in the &agr; or &bgr; configuration; and said substituted morphine having the general structure of Formula 1 in which: R1=hydrogen, acyl, trialkylsilyl, lower alkyl, or methyl-&bgr;-D-(2,3,4-tri-O-acyl)glucuronate; R2=hydrogen; R3=methyl, methyl N-oxide (NMeo), or (CH2)nX, where X=NRR4, R and R4 each being one of hydrogen, alkyl, aryl, acyl and a halogen.