Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1994-02-04
1997-04-15
Kight, John
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
536 181, 536 185, C07H 1500, C07H 1524
Patent
active
056210876
ABSTRACT:
##STR1## Morphine-6-glucuronide or substituted morphine-6-glucuronide of formulae (I) is made by conjugation of a glucuronate ester and/or substituted glucuronate ester with morphine or substituted morphine in the presence of a Lewis acid catalyst and in the absence of silver catalysts and barium hydroxide and other heavy metal derivatives.
REFERENCES:
Kaspersen, F.M., and Van Boeckel, C.A.A., "A review of the methods of chemical synthesis of sulphate and glucuronide conjugates", Xenobiotica, vol. 17, No. 12, 1451-1471, Dec. 1987.
Vlahov, J., and Snatzke, G., "Uber eine verbesserte Synthese von .beta.-Glucosiduronsaure-Derivaten", Liebigs Ann. Chem., 1983, 570-574.
Sy, W.-W., et al., "Syntheses of 3-O- and 6-O-Propanoylmorphine--A Reinvestigation and Correction", Journal of Pharmaceutical Sciences, vol. 75, No. 8, Aug. 1986, 787-789.
Saferstein, R., et al, "Chemical Ionization Mass Spectrometry of Morphine Derivatives", Journal of Forensic Sciences, vol. 24, No. 2, Apr. 1979, 312-316.
Manura, J.J., et al., "The Forensic Identification of Heroin", Journal of Forensic Sciences, vol. 23, No. 1, Jan. 1978, 44-56.
Bollenback, G.N., et al, "The Synthesis of Aryl-D-glucopyranosiduronic Acids", J. American Chemical Society, 1955, 77, 3310-3315.
Osborne, R., et al., "Analgesic Activity of Morphine-6-Glucuronide", The Lancet, 1988, 828.
Carrupt, P-A., et al, "Morphine-6-Glucuronide and Morphine 3-Glucuronide as Molecular Chameleons with Unexpected Lipophilicity", J. Med. Chem., 1991, 34, 1272-1275.
Yoshimura, H., et al., Chem. Pharm. Bull., 1968, 16, 2114.
"Metabolism of Citalopram in Man", abstract, International Society for Study of Xenobiotics, Oct. 21-25, 1994.
Brown Richard T.
Carter Neil E.
Lumbard Keith W.
Mayalarp Stephen P.
Scheinmann Feodor
Kight John
Salford Ultrafine Chemicals and Research Limited
White Everett
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