Synthesis of UDP-glucose: N-acylsphingosine...

Details Synthesis of UDP-glucose: N-acylsphingosine... Synthesis of UDP-glucose: N-acylsphingosine...

2005-02-15

2005-02-15

McKane, Joseph K. (Department: 1626)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

active

06855830

ABSTRACT:
Disclosed is a novel enantiomeric synthesis cermamide-like inhibitors of UDP-glucose: N-acylsphingosine glucosyltransferase. Also disclosed are novel intermediates formed during the synthesis.

REFERENCES:
patent: 5916911 (1999-06-01), Shayman et al.
patent: 5945442 (1999-08-01), Shayman et al.
patent: 5952370 (1999-09-01), Shayman et al.
patent: 5972928 (1999-10-01), Chatterjee
patent: 6030995 (2000-02-01), Shayman et al.
patent: 6051598 (2000-04-01), Shayman et al.
Kurosawa et al., Journal of Labelled Compounds and Radiopharmaceuticals, vol. XXXVIII, No. 3., pp. 285-297, (1996).*
Alker, D., et al., “Application of Enantiopure Templated Azomethine Ylids to β-Hydroxy-α-amino Acid Synthesis,”Tetrahedron: Asymmetry,54: 6089-6098 (1998).
Harwood, L.M., et al., “Double diastereocontrol in the synthesis of enantiomerically pure polyoxamic acid,”Chem. Commun.,pp. 2641-2642 (Sep. 1998).
Harwood, L.M., et al., “Asymmetric Cycloadditions of Aldehydes to Stabilised Azomethine Ylids: Enantiocontrolled Construction of β-Hydroxy-α-amino acid Derivitives,”Tetrahedron: Asymmetry,3(9): 1127-1130 (1992).
Dellaria, Jr., J.F., et al., “Enantioselective Synthesis of α-Amino Acid Derivatives via the Stereoselective Alkylation of a Homochiral Glycine Enolate Synthon,”J. Org. Chem.,54: 3916-3926 (1989).
Vunnam, R.R., et al., “Analogs of Ceramide That Inhibit Glucocerebroside Synthetase in Mouse Brain,”Chemistry and Physics of Lipids,L.D. Bergelson, et al., eds. (Elsevier/North-Holland Scientific Publishers Ltd.), 26: pp. 265-278 (1980).
Shukla, A., et al., “Metabolism of D-[3H] threo-1-phenyl-2-decanoylamino-3-morpholino-1-propanol, an inhibitor of glucosylceramide synthesis and the synergistic action of an inhibitor of microsomal momooxygenase,”J. of Lipid Research,32:713-722 (1991).
Inokuchi, J., et al., “Preparation of the active isomer of 1-phenyl-2-decanoylamino-3-morpholino-1-propanol, inhibitor of murine glucocerebroside synthetase,”J. of Lipid Research,28: 565-571 (1987).
Ogawa, S., et al., “Synthesis and Biological Evaluation of Four Stereoisomers of PDMP-Analogue, N-(2-Decylamino-3-Hydroxy-3-Phenylprop-1-YL)-β-Valienamine, and Related Compounds,”Bioorganic&Medicinal Chemistry Letters,7(14):1915-1920 (1997).
Nishida, A., et al., “Practical Synthesis of threo-(1S, 2S)- and erythro-(1R, 2S)-1-Phenyl-2-palmitoylamino-3-morpholino-1-propanol (PPMP) from L-Serine,”Synlett,pp. 389-390 (Apr. 1998).
Wong, C-H., et al., “Synthesis and Evaluation of Homoazasugars as Glycosidase Inhibitors,” J. Org. Chem. 60:1492-1501, (1995).
Mitchell, S.A., et al., “Glycosyltransferase Inhibitors: Synthesis of D-threo-PDMP, L-threo-PDMP, and Other Brain Glucosylceramide Synthase Inhibitors from D- or L-Serine,”J. Org. Chem.,63: 8837-8842 (1998).
Carson, K.G., et al., “Studies on Morpholinosphingolipids: Potent Inhibitors of Glucosylceramide Synthase,”Tetrahedron Letters,35(17): 2659-2662 (1994).
Abe, A., et al., “Structural and stereochemical studies of potent inhibitors of glucosylceramide synthase and tumor cell growth,”J. of Lipid Research,36: 611-621 (1995).
Abe, A., et al., “Improved Inhibitors of Glucosylceramide Synthase,”J. Biochem.,111:191-196 (1992).
Lee, L., et al., “Improved Inhibitors of Glucosylceramide Synthase,”J. of Biological Chemistry,274(21): 14662-14669 (1999).

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