Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2011-05-03
2011-05-03
Landau, Sharmila Gollamudi (Department: 1611)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
Reexamination Certificate
active
07935726
ABSTRACT:
Provided are compounds of formula IA or IB:wherein R1 and R8 are independently optionally substituted hydrocarbyl groups; wherein(a) R1 contains a carbonyl group and a phenyl group,(b) R8 contains an optionally substituted adenine group, or(c) R8 contains an alkenyl group with from two to six carbon atoms;R10is H, —OH, —OR or ═O; R6 is selected from the group consisting of: H, OH, alkyl, alkenyl, alkynyl, an aromatic ring system, amino, sulfhydryl, sulfonyl, NH2and OCOR; R2 is selected from the group consisting of: H, —OH and lower alkyl; R is H or an optionally substituted hydrocarbyl group, and pharmaceutically acceptable salts or esters of the foregoing, as well as isomers thereof.
REFERENCES:
patent: 5958970 (1999-09-01), Hua et al.
patent: 6384045 (2002-05-01), Hua et al.
patent: 6426341 (2002-07-01), Mylari
Hua et al., Tetrahedron, 2003, 59, 4795-4803.
Aggarwal et al., “A formal synthesis of (+)-pyripyropene a using a biomimetic epoxy-olefin cyclisation: Effect of epoxy alcohol/ether on cyclisation efficiency,” J. Chem. Soc., Perkin Trans I:3315-3321, 1999.
Barbuch, R. et al., “Purification of 9N-[(1′R,3′R)-trans-3′-hydroxycyclopentanyl]adenine HCl: A combination of theory and experiment,” Tetrahedron 53(21):7181-7190, 1997.
Billheimer, J.T., “Cholesterol acyltransferase,” Methods Enzymol. 111:286-293, 1985.
Borcherding, D. R. et al., “Synthesis of analogues of neplanocin A: Utilization of optically active dihydroxycyclopentenones derived from carbohydrates,” J. Org. Chem. 52:5457-5461, 1987.
Carson, J. A. et al., “β-amyloid catabolism: Roles for neprilysin (NEP) and other metallopeptidases?” J. Neurochem. 81:1-8, 2002.
Cervera, M. et al., “4-Amino-6-methyl-2H-pyran-2-one. Preparation and reactions with aromatic aldehydes,” Tetrahedron 46(23):7885-7892, 1990.
Chida, N. et al., “Pd-catalyzed coupling reaction of glycosylamines with 6-chloropurines: Synthesis of 6-(β-D-Mannopyranosylamino) 9H-purine and its β- D—gluco isomer, N-glycoside models for spicamycin and septacidin,” Tetrahedron Lett. 40:2573-2576, 1999.
Corey, E.J. et al., “Oxidative hydrolysis of 1,3-dithiane derivatives to carbonyl compounds using N-halosuccinimide reagents,” J. Org. Chem. 36(23):3553-3560, 1971.
De Clercq, E., “Antiviral and antimetabolic activities of neplanocins,” Antimicrob. Agents Chemother. 28(1):84-89, Jul. 1985.
Ellman, G.L. et al., “A new and rapid colorimetric determination of acetylcholinesterase activity,” Biochem. Pharmacol. 7:88-95, 1961.
Gundersoen, L.-L et al., “6-halopurines in palladium-catalyzed coupling with organotin and organozinc reagents,” Tetrahedron 50(32):9743-9756, 1994.
Hua, D.H. et al., “A one-pot condensation of pyrones and enals. Synthesis of 1H,7H-5a,6,8,9-tetrahydro-1-oxopyrano[4,3−b][1]benzopyrans,” J. Org. Chem. 62(20):6888-6896, 1997.
Hua, D.H. et al., “Syntheses and bioactivities of tricyclic pyrones,” Tetrahedron 59:4795-4803, 2003.
Jin, L.-W. et al., “Novel tricyclic pyrone compounds prevent intracellular APP C99-induced cell death,” Journal of Molecular Neuroscience 19:57-61, 2002.
Kim, Y.K. et al., “Pyripyropenes, novel inhibitors of acyl-CoA:Cholesterol acyltransferase produced byAspergillus fumigatusII. Structure elucidation of pyripyropenes A, B, C and D,” J. Antibiotics 47(2):154-162, Feb. 1994.
Leonard, N. J. et al., “The synthesis of 7-substituted adenines through the use of a blocking group at the 3-position. Site of alkylation of 7-substituted adenines,” J. Am. Chem. Soc. 85:3719, 1963.
Main, A.R. et al., “The purification of cholinesterase from horse serum,” Biochem. J. 143:733-744, 1974.
Marzetta, C.A. et al., “Pharmacological properties of a novel ACAT inhibitor (CP-113,818) in cholesterol-fed rats, hamsters, rabbits, and monkeys,” J. Lipid Res. 35:1829-1838, 1994.
Narasimhan, N.S. et al., “Mechanism of acylation of dilithium salts of β-ketoesters: An efficient synthesis of anibine,” J. Org. Chem 48:3945-3947, 1983.
Obata, R. et al., “Chemical modification and structure-activity relationships of pyripyropenes. 1. Modification at the four hydroxyl groups,” J. Antibiotics 49(11):1133-1148, 1996.
Omura, S. et al., “Pyripyropenes, highly potent inhibitors of Acyl-CoA; Cholesterol acyltransferase produced byAspergillus fumigatus,” J. Antibiot. 46:1168-1169, 1993.
Omura, S. et al., “Arisugacin, a novel and selective inhibitor of acetylcholinesterase fromPenicilliumsp. FO-4259,” J. Antiobiot. 48(7):745-746, Jul. 1995.
Perchellet, E.M., “Tricyclic pyrone analogs: A new synthetic class of bifunctional anticancer drugs that inhibit nucleoside transport, microtubule assembly, the viability of leukemic cells in vitro and the growth of solid tumors in vivo,” Anti-Cancer Drugs 10:489-504, 1999.
Perchellet, J.-P. et al., “Antitumor activity of novel tricyclic pyrone analogs in murine Leukemia cells in vitro,” Anticancer Research 17:2427-2434, 1997.
Puglielli, L. et al., “Acyl-coenzyme A: cholesterol acyltransferase modulates the generation of the amyloid β-peptide,” Nature Cell Biol. 3:905-912, Oct. 2001.
Ralston, J.S. et al., “Acetylcholinesterase from fetal bovine serum,” J. Biol. Chem. 260(7):4312-4318, Apr. 10, 1985.
Rinne, W.W. et al., “New methods of preparation of 2-methylcyclohexen-1-one,” J. Am. Chem. Soc. 72:5759-5760, 1950.
Sambamurti, K. et al., “Advances in the cellular and molecular biology of the beta-amyloid protein in Alzheimer's disease,” Neuro Mol. Med. 1:1-31, 2002.
Sopher, B. L. et al.,“Cytotoxicity mediated by conditional expression of a carboxyl-terminal derivative of the β-amyloid precursor protein,” Mol. Brain Res. 26:207-217, 1994.
Stotter, P.L. et al.,.“α-halocarbonyl compounds. II. A position-specific preparation of α-bromo ketones by bromination of lithium enolates. A position-specific introduction of α,β-unsaturation into unsymmetrical ketones,” J. Org. Chem. 38(14):2576-2578, 1973.
Suckling, K. E. et al., “Role of acyl-CoA:cholesterol acyltransferase in cellular cholesterol metabolism,” J. Lipid Res. 26:647-671, 1985.
Tall, A. R., “Plasma cholesteryol ester transfer protein,” J. Lipid Res. 34:1255-1274, 1993.
Tomoda, H. et al., “Purpactins, new inhibitors of acyl-CoA:cholesterol acyltransferase produced byPenicillium purpurogenum,” J. Antibiot. 44:136-143, Feb. 1991.
Tomoda, H., et al., “Relative and absolute stereochemistry of pyripyropene A, A potent, bioavailable inhibitor of Acyl-CoA:cholesterol acyltransferase (ACAT),” J. Am. Chem. Soc. 116:12097-12098, 1994.
Tomoda, H. et al., “Erabulenols, inhibitors of cholesteryl ester transfer protein produced byPenicilliumsp. FO-5637. I. Production, isolation and biological properties” J. Antibiot. 51(7):618-623, Jul. 1998.
Ukai, T. et al., “Chemistry of dibenzylideneacetone-palladium(0) complexes. I. Novel tris(dibenzylideneacetone)dipalladium(solvent) complexes and their reactions with quinones,” J. Organomet. Chem. 65:253-266, 1974.
Villa, P. et al., “Caspases and caspase inhibitors,” Trends Biochem. Sci. 22:388-393, Oct. 1997.
Yaginuma, S. et al., “Studies on neplanocin A, new antitumor antibiotic. I. Producing organism, isolation and characterization,” J. Antibiot. 34(4):359-366, Apr. 1981.
Aiello et al., (Mar. 1999), “Amelioration of Abnormal Retinal Memodynamics by a Protein Kinase C β-Selective Inhibitor (LY33531) in Patients with Diabetes: Results of a Phase I Safety and Pharmacodynamic Clinical Trial.”IOVS40:S192.
Cervera et al., (1990), “4-Amino-6-Methyl-2H-Pyran-2-One. Preparation and Reactions with A
Greenlee Sullivan P.C.
Kansas State University Research Foundation
Landau Sharmila Gollamudi
Purdy Kyle
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