Anti-cancer and anti-microbial 5-membered heterocyclic...

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

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C548S187000, C548S225000, C548S316400, C548S324100

Reexamination Certificate

active

07378530

ABSTRACT:
Disclosed herein are various novel oxazolidinone, imidazolidinone, and thiazolidinone analogs and methods of treating cancer and/or microbial infection using these analogs. Particular 4-oxazolidinone compounds are shown to have anti-cancer and anti-microbial activity.

REFERENCES:
patent: 2915527 (1959-12-01), Campbell et al.
patent: 2971958 (1961-02-01), Lynn
patent: 3129222 (1964-04-01), Bicking
patent: 3182063 (1965-05-01), Satzinger et al.
patent: 4049816 (1977-09-01), Harnden et al.
patent: 4584385 (1986-04-01), Dirlam
patent: 4629794 (1986-12-01), Dirlam
patent: 4650512 (1987-03-01), Felix et al.
patent: 4769232 (1988-09-01), Chappel et al.
patent: 6387687 (2002-05-01), Naotsuka et al.
patent: 1917615 (1970-10-01), None
patent: 1966053 (1971-04-01), None
patent: WO 98/22450 (1998-05-01), None
Mohareb, 1992, Monatshefte fur Chemie, 123, p. 341-347.
Abell et al., “Chemistry of the Mycalamides: Antiviral and Antitumour Compounds from the New Zealand Marine Sponge. Part 6. The Synthesis and testing of the C(7)-C(10) Fragment,”Journal of the Chemical Society, Perkin Transactions I, pp. 1647-1654, (1997).
Alm et al., “Effects of Topically Applied PGF and its Isopropylester on Normal and Glaucomatous Human Eyes,”Prog. Clin. Biol. Res., 312:447-58, (1989).
Avalos M. et al., “Reactivity of 2-methylthioisomuchnone with Acid Chlorides,”Tetrahedron Letters, vol. 44, No. 25, pp. 4657-4660, (Jun. 16, 2003).
“Bioreversible Carriers in Drug Design: Theory and Application”, ed. E.B. Roche, Pergamon Press: New York, 14-21, (1987).
Bull, A.T. et al., “Search and Discovery Strategies for Biotechnology: the Paradigm Shift,”Microbiol. Mol. Biol. Rev., 64:573, (2000).
Cragg, G.M. & D.J. Newman, “Chemical Diversity: a Function of Biodiversity,”Trends Pharmacol Sci.23:404, (2002).
“Design of Prodrugs” (1985) ed. H. Bundgaard, Elsevier.
Fingl et al., “General Principles,”The Pharmacological Basis of Therapeutics, Ch.1, p. 1, (1975).
Faulkner, D.J. “Marine Natural Products,”Nat Prod Rep.18:1, (2001).
Frenz, J.L.. Kohl, A.C. & R.G. Kerr, “Marine Natural Products as Therapeutic Agents: Part 2.”Exp. Opin. Ther. Patents, 14:17, (2004).
Green and Wuts,Protective Groups in Organic Synthesis, 3rdEd., John Wiley & Sons, New York, NY, (1999).
Gullo et al., “Drug Discovery from Natural Products,”Journal Of Industrial Microbiology and Biotechnology, vol. 33, pp. 523-531, (2006).
Higuchi, T., Stella V., “Pro-drugs as Novel Delivery Systems”,American Chemical Society, A.C.S. Symposium Series, vol. 14, (1975).
Ibrahim et al., “Activated Nitriles in Heterocyclic Synthesis: a Novel Synthesis of Pyrano[2,3-d] pyrimidine, pyrano[2,3-c]pyrazole, pyrano[2,3-d]thiazole & thiazolo[3,2-a]pyridine derivatives,”Indian Journal of Chemistry, Section B, vol. 26B, pp. 216-219, (1987).
Jagodzinski et al., “Reactions of Secondary Beta-Ketothioamides with Ethyl Bromoacetate and Ethyl 2-bromopropionate. The Synthesis of N-substituted 2-acylmethylidene-1,3-thiazolidin-4-ones,”Polish Journal of Chemistry, vol. 74, No. 8, pp. 1101-1114, (2000).
Joshi, A., “Microparticulates for Ophthalmic Drug Delivery,”J. Ocul. Pharmacol., 10(1)29-45, (1994).
Kanamaru, T. et al., “In Vitro and In Vivo Antibacterial Activities of TAK-083, an Agent for Treatment ofHelicobacter pyloriInfection,”Antimicrobial Agents and Chemotherapy, 2455, (2001).
Kanto, J., “Clinical Pharmacokinetics of Ergotamine, dihydroergotamine, ergotoxine, bromocriptine, methysergide, and lergotrile,”Int. J. Clin. Pharmacol., Ther. Toxicol., 21, 135, (1983).
Kerr, R.G. & S.S. Kerr, “Marine Natural Products as Therapeutic Agents,”Exp. Opin. Ther. Patents9:1207, (1999).
Larock, R., Comprehensive Organic Transformations, VCH Publishers, (1989).
Mayer et al., “Efficacy of a Novel Hydrogel Formulation in Human Volunteers,”Ophthalmologica, 210(2):101-3, (1996).
Mayer, A.M. &V.K. Lehmann, “Marine Pharmacology in 1999: Antitumor and Cytotoxic Compounds,”Anticancer Res.21:2489, (2001).
Moore, B.S.. “Biosynthesis of Marine Natural Products: Microorganisms and Macroalgae,”Nat. Prod. Rep.16:653, (1999).
Mordenti, “Intraocular Pharmacokinetics and Safety of a Humanized Monoclonal Antibody in Rabbits after Intravitreal Administration of a Solution or a PLGA Microsphere Formulation,”Toxicol. Sci., 52(1):101-6, (1999).
Okami, Y. “The Search for Bioactive Metabolites from Marine Bacteria,”J Mar Biotechnol.1:59, (1993).
Paquette, L.,Encyclopedia of Reagents for Organic Synthesis, John Wiley and Sons, (1995).
Protective Groups in Organic Chemistry, ed. J.F.W. McOmie, Plenum Press, (1973).
Remington's Pharmaceutical Sciences, 18thEd., Mack Publishing Co., Easton, PA (1990).
Satzinger, G., “Heterocyclen Durch Readtion von Mercapto- und Hydroxycarbonsaureestern mit aktivierten Nitrilen,”Justus Liebigs Annalen der Chemie, 473-511 (1978).
Schach von Wittenau, “The structure of Indolmycin,”JACS, 83, 4678, (1961).
Shedden et al., “Efficacy and Tolerability of Timolol Maleate Ophthalmic Gel-Forming Solution Versus Timolol Opthalmic Solution in Adults with Open-Angle Glaucoma or Ocular Hypertension: A Six-Month, Double-Masked, Multicenter Study.”Clin. Ther., 23(3):440-50 (2001).
Smith, S. et al., “The Alkaloids of Ergot. Part 1.”J.C.S., 1390, (1930).
“Symposium Drug Discovery From Natural Products,”SIM Annual Meeting, Chicago, US, (Aug. 2005).
Van Dormael et al., “Derives acylmethyleniques. II. Merocynanines a Substitution Acylmethylenique,”Bulletin Des Societies Chimiques Belges, vol. 57. pp. 364-372, (1948).
Veronese et al., “Base-Promoted Reactions of Beta-Enaminones with 2-bromo-2-methylpropanamides. Formation of 2-ketonyloxazolidin-4-ones and cyclohexanespriro-oxazolidin-4-ones,”Journal of the Chemical Society, Perkin Transactions I, pp. 781-784, (1984).
Yildirim, I. et al., “Experimental and Theoretical Investigations of Functionalization and Cyclization Reactions of 4-benzoyl-5phenyl1-2,-3-furandione with some acetanilides,”Indian J. Chemistry, vol. 36B, 1138. (1997).
Zaleska et al., “Synthesis of 5-substituted thiazolidine-4-one derivatives,” Die Pharmazie, vol. 50, No. 8, pp. 537-540, (1995).
Zask et al., “Synthesis of 3-mercapto-2(5H)-furnanones via reaction of dilitho-2,4-thiazolidinedione with alpha-halo ketones,”Tetrahedron Letters, vol. 34, No. 17, pp. 2719-2722, (Apr. 23, 1993).
International Search Report for PCT/US2006/006278, Mailed on Dec. 7, 2006.

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