Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1997-07-29
1999-09-28
Raymond, Richard L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
5142245, 5142298, 514267, 514287, 514291, 514292, 514293, 514338, 514432, 514434, 514437, 514452, 514453, 514454, 544 32, 544 34, 544 95, 544250, 544251, 546 64, 546 65, 546 80, 546 81, 546 82, 546 83, 546 89, 546 90, 546 92, 5462801, 5462824, 5462827, 5462831, 549 16, 549 17, 549 24, 549 25, 549 26, 549 27, 549276, 549282, 549361, 549383, 549384, 549387, 549392, 549393, A61K 3135, A61K 3138, A61K 3139, C07D31178, C07D31908, C07D32706, C07D33504, C07D33908
Patent
active
059589701
ABSTRACT:
This invention provides cancer-active tricyclic and tetracyclic oxypyrones and a method of synthesizing these compounds. Preferred compounds have aryl groups at the 3-position of the oxypyrone ring. The tricyclic oxyprone synthetic method is a simple condensation reaction of pyrones with cyclohexenecarboxaldehydes, providing high yields and using few steps. The tetracyclic oxypyrone synthetic method is a simple condensation reaction of carvones with pyrones.
REFERENCES:
Hua, D.H. et al., "A One-Pot Condensation of Pyrones and Enals. Synthesis Journal of Organic Chemistry (Oct. 3, 1997) 62(20):6888-6896.
Perchellet, J.P. et al., "Antitumor Activity of Novel Tricyclic Pyrone Analogs in Murine Leukemia Cells in Vitro," Anticancer Research (Jul.-Aug. 1997) 17(4A):2427-2434.
Billheimer, J.T., "Cholesterol Acyltransferase," (1985) In Methods in Enzymology 111:286-293.
Cervera, M. et al., "4-Amino-6-methyl-2H-pyran-2-one, Preparation and Reactions with Aromatic Aldehydes," (1990) Tetrahedron 46:7885-7892.
Corey, E.J. and Erickson, B.W., "Oxidative hydrolysis of 1,3-dithiane derivatives to carbonyl compounds using N-halo(succinimide) reagents," (1971) J. Org. Chem. 36(3):3553-3560.
Ellman, G.L. et al., "A New and Rapid Colorimetric Determination of Acetylcholinesterase Activity," (1961)Biochemical Pharmacology 7:88-95.
Kim, Y.K. et al., "Pyripyropenes, Novel Inhibitors of Acyl-CoA:Cholesterol Acyltransferase Produced by Aspergillus fumigatus II. Structure Elucidation of Pyripyropenes A, B, C and D," (1994) J. Antibiotics 47:154-162.
Main, A.R. et al., "Purification of cholinesterase from horse serum," (1974) Biochem. J. 143:733-744.
Marzetta, C.A. et al. (1994), "Pharmacological properties of a novel ACAT inhibitor (CP-113,818) in cholesterol-fed rats, hamsters, rabbits, and monkeys," J. Lipid Res. 35:1829-1838.
Narasimhan, N.S. and Ammanamanchi, R., "Mechanism of acylation of dilithium salts of .beta.-ketoesters: an efficient synthesis of anibine," (1983) J. Org. Chem 48:3945-3947.
Obata, R. et al., "Chemical modification and structure-activity relationships of pyripyropenes. 1. Modification at the four hydroxyl group," (1996) J. Antibiotics 49:1113-1148.
Omura, S., et al., "Arisugacin, a Novel and Selective Inhibitor of Acetylcholinesterase from Penicillium sp. FO-4259," (1995) J. Antibiotics 48:745-746.
Omura, S., et al., "Pyripyropenes, Highly Potent Inhibitors of Acyl-CoA; Cholesterol Acyltransferase Produced by Aspergillus fumigatus," (1993) J. Antibiotics 46:1168-1169.
Ralston, J.S. et al., "Acetylcholinesterase from Fetal Bovine Serum," (1985) J. Biol. Chem. 260:4312-4318.
Rinne, W.W. et al., "New methods of preparation of 2-methylcyclohexen-1-one," (1995) J. Am. Chem. Soc. 72:5759-5760.
Stotter, P.L. and Hill, K.A., ".alpha. Halocarbonyl Compounds. II. A Position-Specific Preparation of .alpha.-Bromo Ketones by Bromination of Lithium Enolates. A Position-Specific Introduction of .alpha., .beta.-Unsaturation into Unsymmetrical Ketones," (1973) J. Org. Chem. 38:2576-2578.
Tomoda, H., et al., "Relative and Absolute Stereochemistry of Pyripyropenes A, A Potent, Bioavailable Inhibitor of Acyl-CoA:Cholesterol Acyltransferase (ACAT)," (1994) J. Am. Chem. Soc. 116:12097-12098.
Hua Duy H.
Perchellet Jean-Pierre
Coleman Brenda
Kansas State University Research Foundation
Raymond Richard L.
LandOfFree
Tricyclic and tetracyclic pyrones does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Tricyclic and tetracyclic pyrones, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Tricyclic and tetracyclic pyrones will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-703904