Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2007-03-27
2007-03-27
Anderson, Rebecca (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
active
11091836
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 (2005-02-01), 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: 2002/0198240 (2002-12-01), Shayman et al.
patent: 2003/0073680 (2003-04-01), Shayman et al.
patent: 2005/0009872 (2005-01-01), Hirth et al.
patent: 2005/0049235 (2005-03-01), Shayman et al.
patent: 10324671 (1998-12-01), None
patent: WO 01/04108 (2001-01-01), None
patent: WO 02/062777 (2002-08-01), None
Abdel-Magid, A., et al., “Metal-Assisted Aldol Condensation of Chiral α-Halogenated Imide Enolates: A Stereocontrolled Chiral Epoxide Synthesis,”J. Am. Chem. Soc., 108: 4595-4602 (1986).
Abe, A., et al., “Structural and Stereochemical Studies of Potent Inhibitors of Glucosylceramide Synthase and Tumor Cell Growth,”J. Lipid. Res., 36: 611-621 (1995).
Abe, A., et al., “Improved Inhibitors of Glucosylceramide Synthesis,”J. Biochem., 111: 191-196 (1992).
Abe, A., et al., “Metabolic Effects of Short-Chain Ceramide and Glucosylceramide on Sphingolipids and Protein Kinase C,”Eur. J. Biochem., 210: 765-773 (1992).
Abe, A., et al., “Induction of Glucosylceramide Synthase by Synthase Inhibitors and Ceramide,”Biochim. Biophys. Acta, 1299: 333-341 (1996).
Alon, R., et al., “Glycolipid Ligands for Selectins Support Leukocyte Tethering & Rolling Under Physiologic Flow Conditions,”J. Immunol., 154: 5356-5366 (1995).
Ames, Bruce N., “Assay of Inorganic Phosphate, Total Phosphate and Phosphatases,”Methods Enzymol., 8: 115-118 (1966).
Bielawska, A., et al., “Ceramide-Mediated Biology: Determination of Structural and Stereospecific Requirements Through the Use ofN-Acyl-Phenylaminoalcohol Analogs,”J. Biol. Chem., 167: 18493-18497 (1992).
Bielawska, A., et al., “Modulation of Cell Growth and Differentiation by Ceramide,”FEBS Letters, 307(2): 211-214 (1992).
Blobe, G. C., et al., “Regulation of Protein Kinase C and Role in Cancer Biology,”Cancer Metastasis Rev., 13: 411-431 (1994).
Brenkert, A., et al., “Synthesis of Galactosyl Ceramide and Glucosyl Ceramide by Rat Brain: Assay Procedures and Changes with Age,”Brain Res., 36: 183-193 (1972).
Carson, K. G., et al., “Studies on Morpholinosphingolipids: Potent Inhibitors of Glucosylceramide Synthase,”Tetrahedron Lett., 35:2659-2662 (1994).
Evans, D. A., et al., “Stereoselective Aldol Condensations Via Boron Enolates,”J. Am. Chem. Soc., 103: 3099-3111 (1981).
Felding-Habermann, B., et al., “A Ceramide Analog Inhibits T Cell Proliferative Response Through Inhibition of Glycosphingolipid Synthesis and Enhancement ofN, N-Dimethylsphingosine Synthesis,”Biochemistry, 29: 6314-6322 (1990).
Gatt, S., et al., “Assay of Enzymes of Lipid Metabolism With Colored and Fluorescent Derivatives of Natural Lipids,”Meth. Enzymol., 72: 351-375 (1981).
Hakomori, S., “New Directions in Cancer Therapy Based on Aberrant Expression of Glycosphingolipids: Anti-Adhesion and Ortho-Signaling Therapy,”Cancer Cells, 3(12): 461-470 (1991).
Hammett, L. P.,Physical Organic Chemistry, (NY: McGraw-Hill), (1940).
Högberg, T., et al., “Theoretical and Experimental Methods in Drug Design Applied on Antipsychotic Dopamine Antagonists,” InTextbook of Drug Design and Development, pp. 55-91 (1991).
Hospattankar, A. V., et al., “Changes in Liver Lipids After Administration of 2-Decanoylamino-3-Morpholinopropiophenone and Chlorpromazine,”Lipids, 17(8): 538-543 (1982).
Inokuchi, J., et al., “Antitumor Activity: Via Inhibition of Glycosphingolipid Biosynthesis,”Cancer Letters, 38: 23-30 (1987).
Inokuchi, J., et al., “Inhibition of Experimental Metastasis of Murine Lewis Long Carcinoma by an Inhibitor of Glucosylceramide Synthase and Its Possible Mechanism of Action,”Cancer Res., 50: 6731-6737 (1990).
Inokuchi, J., et al., “Preparation of the Active Isomer of 1-Phenyl-2-Decanoylamino-3-Morpholino-1-Propanol, Inhibitor of Glucocerebroside Synthetase,”J. Lipid Res., 28:565-571 (1987).
Jaffrézou, J., et al., “Inhibition of Lysosomal Acid Sphingomyelinase by Agents which Reverse Multidrug Resistance,”Biochim. Biophys. Acta, 1266: 1-8 (1995).
Kalén, A., et al., “Elevated Ceramide Levels in GH4C1Cells Treated with Retinoic Acid,”Biochim. Biophys. Acta, 1125: 90-96 (1992).
Kopaczyk, K. C., et al., “In VivoConversions of Cerebroside and Ceramide in Rat Brain,”J. Lipid Res., 6: 140-145 (1965).
Nakamura, K., et al., “Coomassie Brilliant Blue Staining of Lipids on Thin-Layer Plates,”Anal. Biochem., 142: 406-410 (1984).
Nicolaou, K.C., et al., “A Practical and Enantioselective Synthesis of Glycosphingolipids and Related Compounds. Total Synthesis of Globotriaosylceramide (Gb3),”J. Am. Chem. Soc., 110: 7910-7912 (1988).
Preiss, J., et al., “Quantitative Measurement ofsn-1,2-Diacylglycerols Present in Platelets, Hepatocytes, andras-andsis-Transformed Normal Rat Kidney Cells,”J. Biol. Chem., 261(19): 8597-8600 (1986).
Radin, N. S., et al., “Ultrasonic Baths as Substitutes for Shaking Incubator Baths,”Enzyme, 45: 67-70 (1991).
Radin, N. S., et al., “Metabolic Effects of Inhibiting Glucosylceramide Synthesis with PDMP and Other Substances,” InAdvances in Lipid Research; Sphingolipids, Part B., R. M. Bell et al., Ed. (San Deigo: Academic Press) vol. 26: 183-213 (1993).
Radin, N. S., et al., “Use of an Inhibitor of Blucosylceramide Synthesis, D-1-Phenyl-2-decanoylamino-3-morpholino-1-propanol,” InNeuroProtocols: A Companion to Methods in Neurosciences, S. K. Fisher et al., Ed., (San Diego: Academic Press) vol. 3: 145-155 (1993).
Rosenwald, A. G., et al., “Effects of Sphingolipid Synthesis Inhibitor on Membrane Transport Through the Secretory Pathway,”Biochemistry, 31: 3581-3590 (1992).
Rosenwald, A. G., et al., “Effects of the Glycosphingolipid Synthesis Inhibitor, PDMP, on Lysosomes in Cultured Cells,”J. Lipid Res., 35: 1232-1240 (1994).
Shayman, J. A., et al., “Modulation of Renal Epithelial Cell Growth by Glucosylceramide: Association with Protein Kinase C, Sphingosine, and Diacylglyceride,”J. Biol. Chem., 266(34): 22968-22974 (1991).
Shayman, J. A., et al., “Glucosphingolipid Dependence of Hormone-Stimulated Inositol Trisphophate Formation,”J. Biol. Chem. 265(21): 12135-12138 (1990).
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 Mooxygenase,”J. Lipid Res., 32: 713-722 (1991).
Shukla, G. S., et al., “Glucosylceramide Synthase of Mouse Kidney: Further Characterization and Improved Assay Method,”Arch. Biochem. Biophys., 283(2): 372-378 (1990).
Shukla, G., et al., “Rapid Kidney Changes Resulting From Glycosphingolipid Depletion by Treatment with a Glucosyltransferase Inhibitor,”Biochim., Biophys. Acta, 1083: 101-108 (1991).
Skehan, P.
Copeland Diane P.
Harris David J.
Nelson Carol A.
Shayman James A.
Siegel Craig
Anderson Rebecca
Genzyme Corporation
Hamilton Brook Smith & Reynolds P.C.
The Regents of the University of Michigan
LandOfFree
Synthesis of UDP-glucose: N -acylsphingosine... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Synthesis of UDP-glucose: N -acylsphingosine..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Synthesis of UDP-glucose: N -acylsphingosine... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3762024