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

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

2007-09-04

2007-09-04

Anderson, Rebecca (Department: 1626)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C548S568000, C548S569000

Reexamination Certificate

active

10916824

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

REFERENCES:
patent: 5707649 (1998-01-01), Inokuchi et al.
patent: 5763438 (1998-06-01), Inokuchi et al.
patent: 5849326 (1998-12-01), Inokuchi et al.
patent: 5907039 (1999-05-01), Jinbo et al.
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: 6040332 (2000-03-01), Shayman et al.
patent: 6051598 (2000-04-01), Shayman et al.
patent: 6255336 (2001-07-01), Shayman et al.
patent: 6335444 (2002-01-01), Jinbo et al.
patent: 6569889 (2003-05-01), Shayman et al.
patent: 6855830 (2005-05-01), Hirth et al.
patent: 6890949 (2005-05-01), Shayman et al.
patent: 6916802 (2005-07-01), Shayman et al.
patent: 2002/0156107 (2002-10-01), Shayman et al.
patent: 2005/0009872 (2005-01-01), Hirth et al.
patent: 10324671 (1998-12-01), None
patent: WO 01/04108 (2001-01-01), None
patent: WO 02/062777 (2002-08-01), None
Inokuchi, et al. “Amino Alcohol Esters as Ceramide Analogs and Pharmaceuticals Containing Them for Treatment of Nerve Diseases,” Abstract of CAPLUS Accession No. 1998:786189, JP 10324671 (1998).
Kurosawa, M., et al., “C-Labeling of a Novel Atypical β-Adrenoceptor Agonist, SM-11044,”Journal of Labelled Compounds and Readiopharmaceuticals, vol. 38(3):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 ofthreo-(1S, 2S)- anderythro-(1R, 2S)-1-Phenyl-2-palmitoylamino-3-morpholino-1-propanol (PPMP) from L-Serine,”Synlett, pp. 389-390 (Apr. 1998).
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 Synthesis,”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).
Wong, C-H., et al., “Synthesis and Evaluation of Homoazasugars as Glycosidase Inhibitors,” J. Org. Chem. 60:1492-1501, (1995).

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