Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2011-03-08
2011-03-08
Shameem, Golam M. M. (Department: 1626)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
C514S279000, C514S375000, C514S410000, C514S411000, C544S230000, C546S035000, C548S218000, C548S421000, C548S439000, C548S448000
Reexamination Certificate
active
07902196
ABSTRACT:
The syntheses of the natural products, avrainvillamide and stephacidin B, are provided. The α,β-unsaturated nitrone functionality of avrainvillamide and its 3-alkylidene-3H-indole 1-oxide core is shown to covalently and reversibly bond to heteroatom-based nucleophiles. This capability may allow these molecules to bind active site nucleophiles and may provide the basis for designing potent and selective enzyme inhibitors. Both avrainvillamide and its dimer stephacidin B have been reported to exhibit antiproliferative activity, and avrainvillamide has been reported to exhibit antimicrobial activity against multi-drug resistant bacteria. Avrainvillamide has been found to target cytoskeleton-linking membrane protein (CLIMP-63) thereby preventing cells from undergoing mitosis. The invention provides syntheses of these natural products as well as analogs of these natural products and their functional cores. The compounds of the invention may be used in the treatment of diseases such as cancer, autoimmune diseases, and bacterial infection.
REFERENCES:
patent: 6066635 (2000-05-01), Fenical et al.
patent: 6291461 (2001-09-01), Qian-Cutrone et al.
patent: 1571193 (2005-09-01), None
patent: WO 2004/053019 (2004-06-01), None
patent: WO 2006/102097 (2006-09-01), None
Myers et al. Journal of the American Chemical Society, 2003, 125 (40), pp. 12080-12081.
Myers et al. J. Am. Chem. Soc., 125: 12080, 2003.
Adams, et al.,Curr. Opin. Chem. Biol., 6:493, 2002.
Bain, et al.,J. Magn. Reson., 188a:21, 1996.
Banwell, et al.,Org. Lett., 5:2497, 2003.
Baran, et al.,Angew. Chem., Int. Ed. Engl., 44:606, 2004.
Barros, et al.,Chem. Eur. J., 6:3991, 2000.
Bassindale, et al.,J. Organomet. Chem., 271:C1, 1984.
Bella, et al.,Org. Biomol. Chem., 2:421, 2004.
Berge, et al.,J. Pharmaceutical Science, 66:1-19, 1977.
Bloch,Chem. Rev., 98:1407, 1998.
Bordwell, et al., J. Am. Chem. Soc., 118:8777, 1996.
Breuza, et al.,J. of Biological Chemistry, 279:47242-47253, 2004.
Colonna, et al.,Gazz. Chim. Ital., 97:1569, 1967.
Corey, et al,J. Am. Chem. Soc., 109:5551, 1987.
Corey, et al.,J. Am. Chem. Soc., 109:7925, 1987.
Corey, et al.,J. Angew. Chem., Int. Ed. Engl., 37:1986, 1998.
Cox, et al.,Tetrahedron Lett., 43:2149, 2002.
Cushing, et al.,J. Am. Chem. Soc., 118:557, 1996.
Dale, et al.,J. Am. Chem. Soc., 95:512, 1973.
Dess, et al.,J. Am. Chem. Soc., 113:7277, 1991.
Elomri, et al.,Heterocycles, 34:799, 1992.
Farah, et al.,J. of Biological Chemistry, 280:9439-9449, 2005.
Frigerio, et al.,J. Org. Chem., 64:4537, 1999.
Ghaffar, et al,J. Mol. Catal. A., 160:249, 2000.
Ghaffar, et al.,Tetrahedron Lett., 36:8657, 1995.
Gutsulyak, et al.,Chemistry of Heterocyclic Compounds, 23:846-849, 1987 [abstract].
Herzon, et al.,J. Am. Chem. Soc., 127:5342-5344, 2005.
International Search Report, PCT/US06/09749, mailed on Nov. 27, 2006.
Ishiyama, et al.,J. Org. Chem., 60:7508, 1995.
Ito, et al.,J. Org. Chem., 43:1011, 1978.
Jackson, et al.,Chem. Commun., 2327, 2000.
Johnson, et al.,Tetrahedron Lett., 33:917, 1992.
Klopfenseein, et al.,EMBO J., 17:6168-6177, 1998.
Klopfenstein, et al.,J. of Cell Biology, 153:1287-1299, 2001.
Knochel, et al.,Tetrahedron, 49:29, 1993.
Kofron, et al.,J. Org. Chem., 41:1879, 1976.
Lau, et al.,J. Org. Chem., 43:1595, 1978.
Lecaille, et al.,Chem. Rev., 102:4459, 2002.
Lissel, et al.,Liebigs Ann. Chem., 263, 1987.
Lombardo, et al.,Synthesis, 6:759, 2000.
Mundy,Biochem. Soc. Trans., 23:572-576, 1995.
Mundy, et al.,J. Cell. Biol., 116:135-146, 1992.
Meyer, et al.,J. Org. Chem., 59:7549, 1994.
Myers, et al.,J. Am. Chem. Soc., 125:12080, 2003.
Nelson, et al.,Tetrahedron, 47:3259, 1991.
Nicolaou, et al.,Angew. Chem., Int. Ed. Engl., 41:993, 2002.
Nussbaum, et al.,Angew. Chem. Int. Ed., 42:3068, 2002.
Ohtani, et al.,J. Am. Chem. Soc., 113:4092, 1991.
Oliveira, et al.,J. Org. Chem., 64:6646, 1999.
Page, et al,J. Org. Chem., 67:7787, 2002.
Pangbom, et al.,Organometallics, 15:1518, 1996.
Qian-Cutrone, et al.,J. Am. Chem. Soc., 124:14556, 2002.
Sanz-Cervera, et al.,J. Am. Chem. Soc., 124:2556, 2002.
Sapountzis, et al,Angew. Chem., Int. Ed. Engl., 41:1610, 2002.
Schaefer, et al.,In the Chemistry of the Cyano Group, The Chemistry of Functional Groups, Wiley and Sons: New York, 1970; pp. 239.
Schweizer, et al.,J. Cell. Sci., 104:671-683, 1993.
Schweizer, et al.,J. Cell. Sci., 104:685-694, 1993.
Schweizer, et al.,J. Cell. Sci., 108:2477-2485, 1995.
Schweizer, et al.,J. Cell. Sci., 126:25-39, 1994.
Spence, et al.,Chem. Rev., 70:231, 1970.
Still, et al,J. Org. Chem., 43:2923, 1978.
Stocking, et al.,Angew. Chem., Int. Ed. Engl., 42:3078, 2003.
Stocking, et al.,J. Am. Chem. Soc., 122:1675, 2000.
Sugie, et al.,J. Antiobiot., 54:911, 2001.
Suginome, et al.,J. Chem. Soc., Perkin Trans., 1:917, 1991.
Sun, et al.,Synthesis, 1249, 1997.
Tae, et al.,Can. J. Chem., 78:689, 2000.
Torri, et al.,Bull. Soc. Chem. Fr., 283, 1978.
Tosi, et al.,Montash. Chem., 118:369, 1987.
Utzinger, et al.,Helv. Chim. Acta., 37:1892, 1954.
Vedrenne, et al.,Mol. Biol. Cell., 16:1928-1937, 2005.
Williams, et al.,J. Am. Chem. Soc., 112:808, 1990.
Williams, et al.,J. Acc. Chem. Res., 36:127, 2003.
Williams, et al.,J. Am. Chem. Soc., 125:12172, 2003.
Wolfe, et al.,J. Am. Chem. Soc., 121:9550, 1999.
International Search Report and Written Opinion for PCT/US2006/009749 mailed Nov. 27, 2006.
International Preliminary Report on Patentability for PCT/US2006/009749 mailed Sep. 27, 2007.
Berger et al., Loss of the NPM1 gene in myeloid disorders with chromosome 5 rearrangements. Leukemia. Feb. 2006;20(2):319-21.
Bertwistle et al., Physical and functional interactions of the Arf tumor suppressor protein with nucleophosmin/B23. Mol Cell Biol. Feb. 2004;24(3):985-96.
Bradford, A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem. May 7, 1976;72:248-54.
Busch et al., Actinomycin D inhibition of monoclonal antibody binding to nucleolar phosphoprotein 37/5.2 (B23). Life Sci. Oct. 22, 1984;35(17):1777-85.
Cazzaniga et al., Nucleophosmin mutations in childhood acute myelogenous leukemia with normal karyotype. Blood. Aug. 15, 2005;106(4):1419-22. Epub May 3, 2005.
Chan, Characterization and cellular localization of nucleophosmin/B23 in HeLa cells treated with selected cytotoxic agents (studies of B23-translocation mechanism). Exp Cell Res. Nov. 1992;203(1):174-81.
Chan et al., Characterization of the cDNA encoding human nucleophosmin and studies of its role in normal and abnormal growth. Biochemistry. Feb. 7, 1989;28(3):1033-9.
Chan et al., Nucleolar protein B23 translocation after doxorubicin treatment in murine tumor cells.
Cancer Res. Jul. 15, 1987;47(14):3798-801.
Chan et al., Nucleophosmin/B23-binding peptide inhibits tumor growth and up-regulates transcriptional activity of p53. Biochem Biophys Res Commun. Jul. 29, 2005;333(2):396-403.
Chen et al., Nucleophosmin gene mutations in acute myeloid leukemia. Arch Pathol Lab Med. Nov. 2006;130(11):1687-92.
Colombo et al., Nucleophosmin is required for DNA integrity and p 19Arf protein stability. Mol Cell Biol. Oct. 2005;25(20):8874-86.
Colombo et al., Nucleophosmin regulates the stability and transcriptional activity of p53. Nat Cell Biol. Jul. 2002;4(7):529-33.
Coutts et al., The p53 response: emerging levels of co-factor complexity. Biochem Biophys Res Commun. Jun. 2005 10;331(3):778-85.
Dalenc et al., Increased expression of a COOH-truncated nucleophosmin resulting from alternative splicing is associated with cellular resistance to ionizing radiation in HeLa cells. Int J Cancer. Aug. 20, 2002;100(6):662-8.
Dhar et al., Specificity protein 1-dependent p53-mediated suppression of human manganese superoxide dismutase gene expression. J Biol Chem. Aug. 4, 2006;281(31):21698-709. Epub Jun. 1, 2006.
Duyster et al., Translocations involving anaplastic lymphoma kinase (ALK). Oncogene. Sep. 10, 2001;20(40):5623-37.
Falini et al., Acute myeloid leukemia carrying cytoplasmic/mutated nucleophosmin (NPMc+AML): biologic and clinical features. Blood. Feb. 1, 2007;109(3):874-85. Epub Sep. 28, 2006.
Falini et al., Cytoplasmic nucleophosmin in a
Herzon Seth B.
Myers Andrew G.
Siegrist Romain
Svenda Jakub
Wulff Jeremy Earle
Otton Alicia L
President and Fellows of Harvard College
Shameem Golam M. M.
Wolf Greenfield & Sacks P.C.
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