Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2005-07-12
2005-07-12
Raymond, Richard L. (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
C514S233800, C514S237800, C514S315000, C514S321000, C514S331000, C514S422000, C514S428000, C544S148000, C544S168000, C546S197000, C546S233000, C548S528000, C548S568000, C548S950000
Reexamination Certificate
active
06916802
ABSTRACT:
The present invention provides amino ceramide-like compounds which inhibit glucosyl ceramide (GlyCer) formation by inhibiting the enzyme GlyCer synthase, thereby lowering the level of glycosphingolipids. The compounds of the present invention have improved GlcCer synthase inhibition activity and are therefore useful in therapeutic methods for treating various conditions and diseases associated with altered glycosphingolipid levels.
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: 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: 6569889 (2003-05-01), 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: WO 01/04108 (2001-01-01), None
patent: WO 02/062777 (2002-08-01), None
Abdel-Magid et al., “Metal-Assisted Aldol Condensation of Chiral A-Halogenated Imide Enolates: A Stereocontrolled Chiral Epoxide Synthesis,”J. Am. Chem. Soc.,108:4595-4602 (1986).
Abe et al., “Structural and Stereochemical Studies of Potent Inhibitors of Glucosylceramide Synthase and Tumor Cell Growth,”J. Lipid. Res.,36:611-621 (1995).
Abe et al., “Improved Inhibitors of Glucosylceramide Synthesis,”J. Biochem.,111:191-196 (1992).
Abe et al., “Metabolic Effects of Short-Chain Ceramide and Glucosylceramide on Sphingolipids and Protein Kinase C,”Eur. J. Biochem.,210:765-773 (1992).
Abe et al., “Induction of Glucosylceramide Synthase by Synthase Inhibitors and Ceramide,”Biochim. Biophys. Acta,1299-333-341 (1996).
Alon et al., “Glycolipid Ligands for Selectins Support Leukocyte Tethering & Rolling Under Physiologic Flow Conditions,”J. Immunol.,154:5356-5366 (1995).
Ames, “Assay of Inorganic Phosphate, Total Phosphate and Phosphates,”Methods Enzymol.,8:115-118 (1966).
Bielawska, A. et al., “Ceramide-Mediated Biology. Determination of Structural and Stereospecific Requirements Through the Use of N-Acyl-Phenylaminoalcohol Analogs,”J. Biol. Chem.,267:18493-18497 (1992).
Bielawska, A. et al., “Modulation of Cell Growth and Differentiation by Ceramide,”FEBS Letters,307:211-214 (1992).
Blobe, G. C. et al., “Regulaton of PKC and Its Role in Cancer Biology,”Cancer Metastasis Rev.,13:411-431 (1994).
Brenkert, A. et al., “Synthesis of Galactosyl Ceramide and Glucosyn Ceramide by Rat Brain: Assay Procedures and Changes with Age,”Brain Res.,36:183-193 (1972).
Carson, K. G. et al., “Studies on Morpholinosphinolipids: Potent Inhibitors of Glucosylceramide Synthase,”Tetrahedron Lett.,35:2659-2662 (1994).
Evans, D. A. et al., “Stereoselective Aldol Condensation 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 of N,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,1 3:461-470 (1991).
Hammett, L. P., In Physical Organic Chemistry, McGraw-Hill, New York (1940).
Hogberg, 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,17:538-543 (1982).
Inokuchi, J. et al., “Antitumor Activity in Mice of an Inhibitor of Glycosphingolipid Biosynthesis,”Cancer Lett.,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).
Jaffrezou, J. et al., “Inhibition of Lysosomal Acid Sphingomyelinase by Agents which Reverse Multidrug Resistance,”Biochim. Biophys. Acta,1266:1-8 (1995).
Kalen, A. et al., “Elevated Ceramide Levels in GH4C1 Cells Treated with Retinoic Acid,”Biochim. Biophys. Acta,1125:90-96 (1992).
Kopaczyk, K. C. et al., “In Vivo Conversions 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.,142:406-41 (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. E. et al., “Quantitative Measurement of SN-1,2-Diacyglycerols Present in Platelets, Hepatocytes, and Ras- and Sis-Transformed Normal Rat Kidney Cells,”J. Biol. Chem.,261:8597-8600 (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,” In Advances in Lipid Research; Sphingolipids in Signaling, Part B., R. M. Bell et al., Ed. (Academic Press, San Diego) 28:183-213 (1993).
Radin, N. S. et al., “Use of 1-Phenyl-2-Decanoylamino-3-Morpholino-1-Propanol (PDMP), an Inhibitor of Glucosylceramide Synthesis,” In NeuroProtocols, A Companion to Methods in Neurosciences, S. K. Fisher, et al., Ed., (Academic Press, San Diego) 3:145-155 (1993).
Rosenwald, A. G., et al., “Effects of Sphingolipid Synthesis Inhibitor on Membrane Transport Through the Secretory Pathway,”Biochemsitry,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 (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.,266:22968-22974 (1991).
Shayman, J. A., et al., “Glucosphingolipid Dependence of Hormone-stimulated Inositol Trisphophate Formation,”J. Biol. Chem.265:12135-12138 (1990).
Shukla, A., et al., “Metabolism of D-[3H]PDMP, an Inhibitor of Glucosylceramide Synthesis, and the Synergistic Action of an Inhibitor of Microsomal Monooxygenase,”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.,283:372-378 (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., et al., “New Colorimetric Cytotoxicity Assay for Anticancer-Drug Screening,”J. Natl. Cancer Inst.,82:1107-1112 (1990).
Strum, J. C., et al., “1-b-D-Arabinofuranosylcytosine Stimulates Ceramide and Diglyceride Formation in HL-60 Cells,”J. Biol. Chem.,269:15493-15497 (1994).
Svensson, M., et al., “Epithelial Glucosphingolipid Expression as a Determinant of Bacterial Adherence and Cytokine Production,”Infect. and Immun.,62:4404-4410 (1994).
Tang, W., et
Copeland Diane P.
Harris David J.
Nelson Carol A.
Shayman James A.
Siegel Craig
Genzyme Corporation
Hamilton Brook Smith & Reynolds P.C.
Raymond Richard L.
The Regents of the University of Michigan
LandOfFree
Amino ceramide-like compounds and therapeutic methods of use does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Amino ceramide-like compounds and therapeutic methods of use, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Amino ceramide-like compounds and therapeutic methods of use will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3391740