5,5-disubstituted-3,4-dihydroxy-2(5H)-furanones and methods of u

Details 5,5-disubstituted-3,4-dihydroxy-2(5H)-furanones and methods of u 5,5-disubstituted-3,4-dihydroxy-2(5H)-furanones and methods of u

1999-05-19

2000-10-24

Dentz, Bernard

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

514444, 514456, 514478, 514473, 548229, 549 60, 549315, 549317, A61K 3142, A61K 31365, C07D40712, C07D30762

Patent

active

061368326

ABSTRACT:
The present invention relates to synthetic methods for the production of both optically active and racemic 5,5-disubstituted-3,4-dihydroxy-2(5H)-furanones; 5-[(4-aryl)-3-butynyl]-3,4-dihydroxy-2(5H)-furanones; 5-(2-arylthio)ethyl-3,4-dihydroxy-2(5H)-furanones; and 5-(2-aryloxy)ethyl-3,4-dihydroxy-2(5H)-furanones. This invention further relates to the use of the above mentioned compounds as anti-inflammatory agents through their action as mixed inhibitors of lipid peroxidation, 5-lipoxygenase, cyclooxygenase-1 and cyclooxygenase-2. The invention further relates to the use of such compounds in the treatment of chronic inflammatory disorders such as asthma, rheumatoid arthritis, inflammatory bowel disease, atherosclerosis, acute respiratory distress syndrome, and central nervous system disorders such as Alzheimer's and Parkinson's disease wherein reactive oxygen species and inflammatory mediators are contributing deleterious factors.

REFERENCES:
patent: 5071872 (1991-12-01), Witiak et al.
patent: 5095126 (1992-03-01), Witiak et al.
patent: 5185366 (1993-02-01), Witiak et al.
patent: 5288751 (1994-02-01), Brooks et al.
patent: 5298526 (1994-03-01), Witiak et al.
patent: 5399721 (1995-03-01), Hopper et al.
patent: 5504107 (1996-04-01), Mantri et al.
patent: 5504108 (1996-04-01), Witiak et al.
Alami et al, 1993, Tetrahedron Lett 34:6403-6.
Berson and Greenbaum, 1958, J Am Chem Soc 80:653-6.
Bisby et al, 1995, Free Rad Biol Med 20:411-20.
Boopathy and Baiasubramanian, 1968, Biochem J 239:371-7.
Brown, 1975, Organic Syntheses via Boranes, John Wiley and Sons, New York, 100, 178.
Buckle and Fenwick, 1989, J Chem Soc Perken Trans 1:477-82.
Buffinton and Doe, 1995, Free Rad Biol Med 19:911-8.
Bundy et al, 1995, J Med Chem 38:4161-3.
Coyle et al, 1993, Science 262:689-95.
DeJarlais et al, 1980, Synth Commun 10:653-60.
Egan and Gale, 1985, J Biol Chem 260;11554-9.
Evanset et al, 1987, Biochem Pharm 36:2035-7.
Frimer et al, 1995, J Org Chem 60:4510-20.
Grisar et al, 1995, J Med Chem 38:453-8.
Gross et al, 1994, Hepato-Gastroenterol 41:320-7.
Halliwell, 1987, FASEB J 1:358-64.
Halliwell, 1991, Drugs 42:569-605.
Hopper et al. (1995) J. Org. Chem. 60:3334-41.
Hvoslef and Pedersen, 1979, Acta Chemica Scand B 33:503-11.
Kato et al, 1988, J Med Chem 31:793-8.
Kerwin, 1995, J Med Chem 38:4343-62.
King and Burns, 1975, the Second conference on Vitamin C, the New York Acadeny of Science, New York.
Lafont et al, 1995, J Clin Invest 95:1018-25.
Mansuy et al, 1996, Biochem Biophys Res Comm 135:1015-21.
Mantri and Witiak, 1994, Curr Med Chem 1:328-55.
Marshall et al, 1986, J Org Chem 51:858-63.
Maxwell, 1995, Drugs 49:345-61.
Millar et al, 1996, J Org Chem 51:4726-8.
Nicolaou and Webber, 1984, J Chem Soc, Chem Commun 350-1.
Nihro et al, 1992, J Med Chem 35:1618-23.
Nunes et al, 1995, Thromb Vasc Biol 15:156-65.
Ochiai et al, 1991,J Am Chem Soc 113:1319-23.
O'Sullivan et al,1992, Biochem Biophys Res Comm 187:1123-7.
Rabinovici et al, 1993, J Appl Physiol 74:1791-802.
Remacle et al, 1995, Mutat Res 316:103-22.
Saeva et al, 1991, J Am Chem Soc 113:5333-7.
Schank, 1972, Synthesis 176-90.
Schreck et al, 1992, Free Rad Res Comms 17:221-37.
Shimuzu et al, 1984, Pro Natl Acad Sci USA 81:689-93.
Silverman, 1992, The Organic Chemistry of Drug Design and Drug Action, Academic Press, San Diego, CA, 19-20.
Steinberg, 1995, Lancet 346:36-8.
Stork and Rychnovsky, 1987, J Am Chem Soc 109:1564-5.
Sun, 1990, Free Rad Biol & Med 8:583-99.
Triozzi et al, 1993, Int J Immunopharmac 15:47-54.
Wang et al, 1996, Pharm Exp Therap 277:714-20.
Wimalasena et al, 1994, Biochem Biophys Res Comm 200:113-9.
Witiak et al, 1982, J Med Chem 25:90-3.
Witiak et al, 1986, J Med Chem 29:2170-4.
Witiak et al, 1987, J Org Chem 52:2324-7.
Witiak et al, 1987, Actual Chim Therap 15:41-62.
Witiak et al, 1988, J Med Chem 31:1437-45.
Witiak et al, 1992, in Trends in Medicinal chemistry '90, Proceeding of the XIth Internatinal Symposiumon Medicinal Chemistry, Jerusalem, Israel, Sep. 2-7, Sarel et al eds. Blackwell Scientific Publicstions, Oxford, London :243-56.

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