Compounds and their uses

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Carbohydrate doai

Reexamination Certificate

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C536S004100, C536S017200, C536S018400

Reexamination Certificate

active

06953781

ABSTRACT:
Compounds having a mimetic or antagonistic property of an inositol phosphoglycan, and the uses of these compounds are disclosed, together with the use, e.g. to treat a condition ameliorated by administration of an IPG second messenger or an IPG antagonist thereof. In particular, the compounds are based on the 1,6 linkage of a sugar residue and a cyclitol.

REFERENCES:
patent: 5268272 (1993-12-01), Mullner et al.
patent: 5395828 (1995-03-01), Schiebler et al.
patent: 5550166 (1996-08-01), Ostlund et al.
patent: 5652221 (1997-07-01), Larner et al.
patent: 6004938 (1999-12-01), Frick et al.
patent: 6271204 (2001-08-01), Rademacher et al.
patent: 6716826 (2004-04-01), Martin-Lomas et al.
patent: 6759390 (2004-07-01), Martin-Lomas et al.
patent: 0 520 372 (1992-12-01), None
patent: 0 559 064 (1993-09-01), None
patent: 0 845 475 (1998-06-01), None
patent: 63196596 (1988-08-01), None
patent: 03237101 (1991-10-01), None
patent: 04120089 (1992-04-01), None
patent: 06293790 (1994-10-01), None
patent: WO 96/14075 (1996-05-01), None
patent: WO 98/10791 (1998-03-01), None
patent: WO 98/11116 (1998-03-01), None
patent: WO 98/11117 (1998-03-01), None
patent: WO 98/11435 (1998-03-01), None
patent: WO 98/50049 (1998-11-01), None
patent: WO 99/06421 (1999-02-01), None
patent: WO 99/38516 (1999-08-01), None
patent: WO 00/15254 (2000-03-01), None
patent: WO 00/39141 (2000-07-01), None
Schweizer, T.F. et al, J. Sci.Fd. Agric., 1978, 29, 148-154.
Fernandez de la Pradilla, R. et al., “Improved preparation of acetals of myo-inositol and its (±)-1-benzyl ether: conformational analysis of di-O-isopropylidene-myo-inositol derivatives”; Carbohydrate Research, 207: 249-257 (1990).
Bernabé, M. et al., “Chiral recognition of 1-O-allyl and 1-O-benzyl-D- and -L- myo-inositol by cyclomalto-hexaose and -heptaose (α-and β-cyclodextrin)”; Carbohydrate Research, 208: 255-259 (1990).
Zapata, A. et al., “Novel Highly Regioselective O-Alkylation and O-Acylation of myo-Inositol”; J. Org. Chem., 56: 444-447 (1991).
Jaramillo, C. et al., “Synthesis of 1D-1,2-anhydro-myo-inositol”; Carbohydrate Research, 209: 296-298 (1991).
Jaramillo, C. et al., “Approaches to the Synthesis of Glycosyl Phosphatidyl Inositols. Enantioselective Synthesis of Optically Active chiro- and myo-Inositols.”; Tetrahedron Letters, 32(22): 2501-2504 (1991).
Vasella, A. et al., “194. Convenient Synthesis of 2-Azido-2-deoxy-aldoses by Diazo Transfer”; Helvetica Chimica Acta, 74: 2073-2077 (1991).
Aguiló, A. et al., “The Regioselective Synthesis of Enantiomerically Pure myo-Inositol Derivatives. Efficient Synthesis of myo-Inositol 1,4,5-triphosphate.”; Tetrahedron Letters, 33(3): 401-404 (1992).
Zapata, A. et al., “Building blocks for the synthesis of glycosyl-myo-inositols involved in the insulin intracellular signalling process”; Carbohydrate Research, 234: 93-106 (1992).
Caro, H. et al., “Syntheses and insulin-like activity of phosphorylated galactose derivatives”; Carbohydrate Research, 240: 119-131 (1993).
Singh, K. et al., “Synthesis of Oligosaccarides Structurally Related to E-Selectin Ligands”, J. Chem. Soc., Chem. Commun., 775-776 (1994).
Chiara, J.L. et al., “A Stereoselective Route to Enantiomerically Pure myo-Inositol Derivatives Starting from D-Mannitol”, Tetrahedron Letters, 35(18): 2969-2972 (1994).
Zapata, A. et al., “Synthesis and investigation of the possible insulin-like activity of 1D-4-O- and 1D-6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)- myo-inositol 1-phosphate and 1D-6-O-(2-amino-2-deoxy-α-D- glucopyranosyl)- myo-inositol 1,2-(cyclic phosphate)”; Carbohydrate Research, 264: 21-31 (1994).
Jaramillo, C. et al., “An Effective Strategy for the Synthesis of 6-O-(2-Amino-2-deoxy-α-D-glycopyranosyl)-D-chiro- and -D-myo-inositol 1-Phosphate Related to Putative Insulin Mimetics”; J. Org. Chem., 59: 3135-3141 (1994).
Varela-Nieto, I. et al., “Cell Signalling by Inositol Phosphoglycans from Different Species”; Comp. Biochem. Physiol., 115B(2): 223-241 (1996).
Martin-Lomas, M. et al., “The solution conformation of glycosyl inositols related to inositolphosphoglycan (IPG) mediators”; Tetrahedron: Asymmetry, 11: 37-51 (2000).
Baeschlin, D.K. et al., “1,2-Diacetals in Synthesis: Total Synthesis of a Glycosylphosphatidylinositol Anchor ofTrypanosoma brucei”;Chem. Eur. J., 6(1): 172-186 (2000).
Frick, W. et al., “Structure-Activity Relationship of Synthetic Phosphoinositolglycans Mimicking Metabolic Insulin Action”; Biochemistry, 37(38): 13421-13436 (1998).
Jaworek, C.H. et al., “Synthesis of an Inositol-Containing Trisaccharide Related to Insulin Signal Transduction”; Tetrahedron Letters, 40: 667-670 (1999).
Deeg, M.A. et al., “Inositol Glycan Phosphate Derived from Human Erythrocyte Acetylcholinesterase Glycolipid Anchor and Inositol Cyclic 1,2-Phosphate Antagonize Glucagon Activation of Glycogen Phosphorylase”; Diabetes, 42(9): 1318-1323 (1993).
Güther, M.L.S. et al., “Molecular species analysis and quantification of the glycosylphosphatidylinositol intermediate glycolipid C fromTrypanosoma brucei”;Mol. Biochem. Parasitol., 77(2): 137-145 (1996).
Mayer, T.G. et al., “Glycosyl Phosphatidylinositol (GPI) Anchor Synthesis Based on Versatile Building Blocks—Total Synthesis of a GPI Anchor of Yeast”; Eur. J. Org. Chem. 1153-1165 (1999).
Müller, G. et al., “Phosphoinositolglycan-Peptides from Yeast Potently Induce Metabolic Insulin Actions in Isolated Rat Adipocytes, Cardiomyocytes, and Diaphragms”; Endocrinology, 138: 3459-3475 (1997).
Baeschlin, D.K. et al., “Rapid Assembly of Oligosaccharides: Total Synthesis of a Glycosylphosphatidylinositol Anchor ofTrypanosoma brucei”;Angew. Chem. Int. Ed., 37(24): 3423-3427 (1998).
Derappe, C. et al., “Characterization of a New Oligosaccharide Containing myo-Inositol Found in Pregnancy Urine”; Carbohydrate Research, 115: 221-229 (1983).
Angyal, S.J. et al., “Cyclitols. Part XXII. Synthesis of Some Mannosyl- and Mannosyl-mannosyl-myoinositols, and of Galactinol”; J. Chem. Soc. (C), 433-438 (1966).
Reddy, K.K. et al., “Insulin Second Messengers: Synthesis of 6-O-(2-Amino-2-deoxy-α-D-glycopyranosyl)-D-chiro-inositol-1-phosphate”; Tetrahedron Lets., 34(49): 7869-7872 (1993).
Plourde, R. et al., “Synthesis of a Potentially Insulin-Mimetic Phosphodisaccharide”, Tetrahedron Lets., 31(19): 2693-2696 (1990).
Stralfors, P., “Insulin second messengers”; Bioessays, 19: 327-335 (1997).
Field, M.C., “Is there evidence for phospho-oligosaccharides as insulin mediators?”; Glycobiology, 7: 161-168 (1997).
Jones, D.R. et al., “The role of glycosyl-phosphatidylinositol in signal transduction”; Int. J. Biochem. Cell Biol., 39: 313-326 (1998).
Mato, J.M. et al., “Partial Structure of an Insulin-Sensitive Glycophospholipid”; Biochem. Biophys. Res. Commun., 146: 764-770 (1987).
Larner, J., “Rat Liver Insulin Mediator Which Stimulates Pyruvate Dehydrogenase Phosphatase Contains Galactosamine and D-Chiroinositol”; Biochem. Biophys. Res. Commun., 151: 1416-1426 (1988).
Caro, H.N. et al., “Isolation of Partial Characterisation of Insulin-Mimetic Inositol Phosphoglycans from Human Liver”; Biochem. Mol. Med., 61: 214-228 (1997).
Gigg, R. et al., “Synthesis of Glycosylphosphatidylinositol Anchors”; in “Glycopeptides and Related Compounds”; Large & Warren, Eds., Marcel Dekker, New York, 327-392 (1997).
Corey, E.J. et al., “Protection of Hydroxyl Groups as tert-Butyldimethylsilyl Derivatives”; J. Am. Chem. Soc., 94: 6190-6191 (1972).
Ley, S.V. et al., “Cyclohexane-1,2-diacetals (CDA): A New Protecting Group for Vicinal Diols in Carbohydrates”; Angew. Chem. Int.

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