Substituted fused heterocyclic C-glycosides

Details Substituted fused heterocyclic C-glycosides Substituted fused heterocyclic C-glycosides

2009-09-11

2010-10-19

McIntosh, III, Traviss C (Department: 1623)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Carbohydrate doai

Reexamination Certificate

active

07816328

ABSTRACT:
This invention relates to substituted fused heterocyclic C-glycosides, compositions containing them, and methods of using them, for example, for the treatment or prophylaxis of diabetes and Syndrome X.

REFERENCES:
patent: 4584369 (1986-04-01), Klein et al.
patent: 5424406 (1995-06-01), Tsujihara et al.
patent: 5731292 (1998-03-01), Tsujihara et al.
patent: 5767094 (1998-06-01), Tsujihara et al.
patent: 5780483 (1998-07-01), Widdowson et al.
patent: 5830873 (1998-11-01), Tsujihara et al.
patent: 6048842 (2000-04-01), Tsujihara et al.
patent: 6153632 (2000-11-01), Reiveley
patent: 6297363 (2001-10-01), Kubo et al.
patent: 6414126 (2002-07-01), Ellsworth et al.
patent: 6515117 (2003-02-01), Ellsworth et al.
patent: 6562791 (2003-05-01), Maurya et al.
patent: 6617313 (2003-09-01), Maurya et al.
patent: 6627611 (2003-09-01), Tomiyama et al.
patent: 6683056 (2004-01-01), Washburn et al.
patent: 6774112 (2004-08-01), Gougoutas
patent: 7094763 (2006-08-01), Rybczynski et al.
patent: 7482330 (2009-01-01), Rybczynski et al.
patent: 2003/0114390 (2003-06-01), Washburn et al.
patent: 579204 (1994-01-01), None
patent: WO 01/16122 (2001-03-01), None
patent: WO 01/16123 (2001-03-01), None
patent: WO 01/27128 (2001-04-01), None
patent: WO 01/64669 (2001-09-01), None
patent: WO 01/68660 (2001-09-01), None
patent: WO 01/74835 (2001-10-01), None
patent: WO 01/74834 (2001-11-01), None
patent: WO 02/083066 (2002-10-01), None
patent: WO 02/098893 (2002-12-01), None
patent: WO 03/000712 (2003-01-01), None
patent: WO 03/011880 (2003-02-01), None
patent: WO 03/020737 (2003-03-01), None
patent: WO 03/080634 (2003-10-01), None
patent: WO 03/087093 (2003-10-01), None
patent: WO 2004/080990 (2004-09-01), None
patent: WO 2004/087727 (2004-10-01), None
Hongu, M. et al. “Na+ -Glucose Cotransporter Inhibitors as Antidiabetic Agents. II. Synthesis and Structure-Activity Relationships of 4′-Dehydroxyphlorizin Derivatives”, Chem. Pharm. Bull. 46(1) (1998), pp. 22-33.
Ohsumi, K. et al. “Pyrazole-O-Glucosides as Novel Na+ -Glucose Cotransporter (SGLT) Inhibitors” Bioorganic & Medicinal chemistry Letters 13 (2003) pp. 2269-2272.
Tanaka, H. et al. “Solid-Phase Synthesis of β-Mono-Substituted Ketones and an Application to the Synthesis of a Library of Phlorizin Derivatives”, Letter (2002) pp. 1427-1430.
Somei, M. et al., “The First and Simple Total synthesis of Cappariloside A1” Heterocycles, vol. 53, No. 7, (2000) pp. 1573-1578.
Tsujihara, K. et al., “Na+ -Glucose Cotransporter (SGLT) Inhibitors as Antidiabetic Agents. 4. Synthesis and Pharmacological Properties of 4′-Dehydroxyphlorrizin Derivatives Substituted on the B Ring”, J. Med. Chem. (1999) 42, pp. 5311-5324.
Tsujihara, K. et al., “Na+ -Glucose Cotransporter (SGLT) Inhibitors as Antidiabetic Agents. 4. Synthesis and Pharmacological Properties of 4′-Dehydroxyphlorrizin Derivatives Substituted on the B Ring”, Chem. Pharm. Bull. vol. 44, No. 6, (1996) pp. 1174-1180.
Fresneda, P.M. “Synthesis of the indole alkaloids meridianins from the tunicateAplidium meridianum” Tetrahedron 57 (2001) pp. 2355-2363.
Ketcha, D. M. et al., “Synthesis of Alyl-Substituted N-Protected Indoles via Acylation and Reductive Deoxygenation1” J. Org. Chem. (1989) 54, pp. 4350-4356.
Blair, J.B. et al., “Effect of Ring Fluorination on the Pharmacology of Hallucinogenic Tryptamines”, J. Med. Chem. (2000), 43, 4701-4710.
Appleton, J.E. et al, “A Mild and Selective C-3 Reductive Alkylation of Indoles”, Tetrahcdron Letters, vol. 34, No. 9, (1993) pp. 1529-1532.
Comins, D.L. et al., “Synthesis of 3-Substituted Indoles Via N-Acylindolium Ions”, Tetrahedron Letters, vol. 27, No. 17, (1986) pp. 1869-1872.
Dillard, R.D. et al., “Indole Inhibitors of Human Nonpancreatic Secretory Phospholipase A2. 1. Indole-3-acetamides”, J. Med. Chem. (1996) 39, pp. 5119-5136.
Ellsworth, B.A. et al., “C-Arylglucoside synthesis: triisopropylsilane as a selective reagent for the reduction of an anomeric C-phenyl ketal” Tetrahedron: Ssymmetry 14 (2003) pp. 3243-3247.
Link, J.T. et al., “A method for preparing C-glycosides related to phlorizin” Tetrahedron Letters 41 (2000) pp. 9213-9217.
Czernecki, S. et al., “C-Glycosides. 7. Stereospecific C-Glycosylation of Aromatic and Heterocyclic Rings”, J. Org. Chem. 54, (1989) pp. 610-612.
Dondoni, A. et al., “Stereoselective synthesis of C-glycosylphosphonates from their ketols. Reconsideration of an abandoned route”, Tetrahedron: Asymmetry 11 (2000) pp. 305-317.
Benhaddou, R. et al.,“Tetra-n-propylammonium tetra-oxoruthenate (VII): a reagent of choice for the oxidation of diversely protected glycopyranosses and glycofuranoses to lactones”, Carbohydrate Research 260 (1994) pp. 243-250.
Dondoni, A. et al., “Thiazole-Based Synthesis of Formyl C-Glycosides”, J. Org. Chem. 59 (1994) pp. 6404-6412.
Brooks, Paige R. et al., “Boron Trichloride/Tetra-n-Butylammonium Iodide: A Mild, Selective Combination Reagent for the Cleavage of Primary Alkyl Aryl Ethers”, J. Org. Chem. (1999), 64, pp. 9719-9721.
Boehm, H-J et al., “Novel Inhibitors of DNA Gyrase: 3D Structure Based Biased Needle Screening, Hit Validation by Biophysical Methods, and 3D Guided Optimization. A Promising alternative to Random Screening”, J. Med. chem. (2000), 43, 2664-2674.
Orjales, A. et al. “New 2-Piperazinylbenzimidazole Derivatives as 5-HT3 Antagonists. Synthesis and Pharmacological Evaluation” J. Med. Chem. (1997), 40, pp. 586-593.
Mewshaw, R.E. et al., “New Generation Dopaminergic Agents. 7. Heterocyclic Bioisosteres That Exploit the 3-OH-Phenoxyethylamine D2 Template”, Bioorganic & Medicinal Chemistry Letters 9 (1999) pp. 2593-2598.
Wolff, Manfred E., “Burger's Medicinal Chemistry, 5ed., Part 1”, John Wiley & Sons, 1995, pp. 975-977.
Banker, G.S. et al., “Modern Pharmaceutics, 3ed.”, Marcel Dekker, New York, 1996, p. 596.
Goodman & Gilman's: The Pharmacological Basis of Therapeutics, 10th Edition, McGraw-Hill Medical Publishing Division, 2001,pp. 54-56.
Unger et al., “Hyperglycaemia as an inducer as well as a consequence of impaired isle cell function and insulin resistance: implications for the management of diabetes.”, Diabetologia, 1985, vol. 28, pp. 119-121.
Rosetti et al., “Glucose Toxicity.”, Diabetes Cares, 1990, vol. 13, (6), pp. 610-630,abstract only.
Rosetti et al., “Correction of Hyperglycemia with Phlorizin Normalizes Tissue Sensitivity to Insulin in Diabetic Rats.”, Journal of Clinical Investigation, 1987, vol. 79, (5), pp. 1510-1515.
Peng et al., “Post-transcriptional regulaton of Na+/Glucose Cotransporter (SGTL1) Gene Expression in LLC-PK1 Cells.”, Journal of Biological Chemistry, 1995, vol. 270 (35), pp. 20536-20542.
Meanwell et al., “Regiospecific Functionalization of 1,3-Dihydro-2H-benzimidazol-2-one and Structurally Related Cyclic Urea Derivates.”, J. Org. Chemistry, 1995, vol. 60, pp. 1565-1582.
Devivar et al., “Benzimidazole Ribonucleosides: Design, Synthesis, and Antiviral Activity of Certain 2-(Alkylthio)- and 2-(Benzylthio)-5,6-dichloro-1-(β-D-ribofuranosyl)benzimidazoles1.”, J.Med.Chem., vol. 37, 1994, pp. 2942-2949.
PCT International Search Report dated Nov. 9, 2005 for PCT/US04/24625 which relates to U.S. Appl. No. 10/903,136.

Affiliated with

Also associated with

Rating

Substituted fused heterocyclic C-glycosides does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Substituted fused heterocyclic C-glycosides, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Substituted fused heterocyclic C-glycosides will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-4192737