Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2005-09-12
2008-12-16
Berch, Mark L (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
C540S203000, C540S200000, C548S230000
Reexamination Certificate
active
07465720
ABSTRACT:
Disclosed is a total synthesis of a biologically active β-Lactam—Compound 3, which is related to Salinosporamide A and Omuralide, both structurally and by its activity as a proteasome inhibitor.Also disclosed are proteasome inhibiting compounds having the formula:wherein:R1is a cyclolower alkyl group; or R1is a lower alkyl group; and R2is either hydrogen or a lower alkyl group; R3is either hydrogen or a lower alkyl group; R4a halo-lower alkyl group; and R5is either hydrogen or a lower alkyl group.
REFERENCES:
patent: 5756764 (1998-05-01), Fenteany et al.
patent: 5869675 (1999-02-01), Omura et al.
patent: 6133308 (2000-10-01), Soucy et al.
patent: 6147223 (2000-11-01), Fenteany et al.
patent: 6214862 (2001-04-01), Fenteany et al.
patent: 6294560 (2001-09-01), Soucy et al.
patent: 6335358 (2002-01-01), Fenteany et al.
patent: 6458825 (2002-10-01), Fenteany et al.
patent: 6566553 (2003-05-01), Soucy et al.
patent: 6645999 (2003-11-01), Schreiber et al.
patent: 2003/0157695 (2003-08-01), Fenical et al.
patent: 2004/0138196 (2004-07-01), Fenical et al.
patent: 2005/0203162 (2005-09-01), Xiao et al.
patent: WO 96/32105 (1996-10-01), None
patent: WO 02/094311 (2002-11-01), None
patent: WO 2004/071382 (2004-08-01), None
patent: WO 2005/002572 (2005-01-01), None
Hogan, Philip et al., Journal of the American Chemical Society (2005), 127(44), 15386-15387.
Ritonovir <http://aidsinfo.nih.gov/DrugsNew/DrugDetailNT.aspx?MenuItem=Drugs&Search=On&int—id=244> downloaded from the internet Nov. 23, 2007.
Norvir (ritonavir) <http://www.hivandhepatitis.com/hiv—and—aids
orvir—effects.html> downloaded from the internet Nov. 23, 2007.
Yeh et al, J Neurochem. Aug. 2005;94(4):943-56.
Rockwell et al., Archives of Biochemistry and Biophysics vol. 374, Issue 2, Feb. 15, 2000, pp. 325-333.
Tabuchi Alzheimer's and Dementia vol. 2, Issue 3, Supplement 1, Jul. 2006, p. S628.
Ding et al., The FASEB Journal. 2006;20:1055-1063.
Momose et al., Heterocycles 1999, vol. 51, No. 6, pp. 1321-1343.
Manchand, J. Org. Chem. 1992, 57, 3473-3478.
Goldberg et al., Nature Medicine, vol. 8, No. 4, 338-340 (2002).
Feeling, R.H.; Buchanan, G.O.; Mincer, T.J.; Kauffman, C.A.; Jensen, P.R.; Fenical, W., Angew. Chem. Int. Ed., Salinosporamide A: A highly Cytotoxic Proteasome Inhibitor from a Novel Microbial Source, a Marine Bacterium of the New GenusSalinospora, 2003, 42, 355-357.
Corey, E.J.; Li, Wei-Dong., Z. Total Synthesis and Biological Activity of Lactacystin, Omuralide and Analogs, Chem. Pharm. Bull., 1999, 47, 1-10.
Corey, E.J., Reichard, G.A.; Kania, R., Studies on the Total Synthesis of Lactacysin. An improved Aldol Coupling reaction and a β-Lactone Intermediate in Thiol Ester Formation, Tetrahedron Lett., 1993, vol. 34, No. 44, 6977-6980.
Corey, E. J.; Reichard, G. A., Total Synthesis of Lactacysin, J. Am. Chem. Soc., 1992, 114, 10677-10678.
Fenteany, G.; Standaert, R.F.; Reichard, G. A.; Corey, E. J.; Schreiber, S. L., A β-lactone related to lactacystin induces neurite outgrowth in a neuroblastoma cell line and inhibits cell cycle progression in an osteosarcoma cell line. Proc. Natl. Acad. Sci. USA, 1994, 91, 3358-3362.
Omura, S., Fujimoto, T., Otoguro, K., Matsuzaki, K., Moriguchi, R., Tanaka, H., Sasaki, Y., Lactacystin, A novel Microbial Metabolite, induces Neuritogenesis of Neuroblastoma Cells, A., J. Antibiot., 1991, 44, 113-116.
Omura, S., Matsuzaki, K., Fujimoto, T., Kosuge, K., Furuya, T., Fujita, S., Nakagawa, Structure of Lactacystin, a new microbial metabolite which induces differentiation of Neuroblastoma Cells, A., J. Antibiot., 1991, 44, 117-118.
Mincer, Tracy, J., Jensen, Paul, R., Kauffman, Christopher, A., and Fenical William, Widespread and Persistent Populations of a Major new Marine Actinomycete Taxon in Ocean Sediments, Appl. Environ. Microbiol., 68, 5005 (2002).
Wilson, Elizabeth, K., Plumbing the Ocean Depths for Drugs, Chemical & Engineering News, vol. 81, No. 3, pp. 37-38 (2003).
Frank, S. A.; Mergott, D. J., Roush, W. R., The Vinylogous Intramolecular Morita—Baylis—Hillman Reaction: Synthesis of Functianalized Cyclopentenes and Cyclohexenes with Trialkylphosphines as Nucleophilic Catalysts, J. Am. Chem. Soc., 2002, 124, 2404-2405.
Mergott, D.J., Frank, S. A., Roush, W. R., Application of the Intramolecular Vinylogous Morita-Baylis-Hillman Reaction toward the Synthesis of the Spinosyn A Tricyclic Nucleus, Org. Lett., 2002, vol. 4, No. 18, 3157-3160.
Aggarwal, V. K., Emme, I., Fulford, S. Y., Correlation between pKaand Reactivity of Quinuclidine-Based Catalysts in the Baylis-Hillman Reaction: Discovery of Quinuclidine as Optimum Catalyst Leading to Substantial Enhancement of Scope, J. Org. Chem., 2003, 68, 692-700.
Yeo, J. E., Yang, X., Kim, H.J., Koo, S., The intramolecular Baylis-Hillman reaction: easy preparation of versatile substrates, facile reactions, and synthetic applications, J. Chem. Soc., Chem. Commun., 2004, 236-237.
Bols, M., Skrydstrup, T., Silicon-Tethered Reactions, Chem. Rev., 1995, 95, 1253-1277.
Fleming, I., Barbero, A., Walter, D., Sterechemical Control in Organic Synthesis Using Silicon-Containing Compounds, Chem. Rev., 1997, 97, 2063-2092.
Stork, G., Mook, R., Biller, S.A., Rychnovsky, S. D., Free-Radical Cyclization of Bromoacetals. Use in the Construction of Bicyclic Acetals and Lactones. J. Am. Chem. Soc., 1983, 105, 3741-3742.
Stork, G., Sher, P. M., Chen, H.L., Radical Cyclization-Trapping in the Synthesis of Natural Products. A Simple, Stereocontrolled Route to Prostaglandin F2α. J. Am. Chem. Soc., 1986, 108, 6384-6385.
Miyake, H., Yamamura, K., Pd(0) Catlyzed Hydrostannation of Conjugated Dienes. A Facile and Highly Regio- and Stereoselective Synthesis of (Z)-2-Alkenylstannanes. Chem. Lett., 1992, 507-508.
Jones, G. R., Landais, Y., The Oxidation of the Carbon-Silicon Bond, Tetrahedron, 1996, 52, 7599-7662.
Corey, E. J., Li, W., Nagamitsu, T., An Efficient and Concise Enantioselective Total Synthesis of lactacystin, Angew. Chem. Int, Ed., 1998, 37, 1676-1679.
Corey, E.J., and Wei-Dong, Z., Total Synthesis and Biological Activity of Lactacystin, Omuralide and Analogs, Chem. Pharm. Bull., 1999, 47, 1-10.
Corey, E., and Wei-Dong, Z., “An Efficient Total Synthesis of a New and Highly Active Analog of Lactacystin,” Tetrahedron Letters, vol. 39(41), pp. 7475-7478 (Oct. 1998).
Panek, J., and Masse, C., “Total Synthesis of (+)-Lactacystin,” Agnew. Chem. Int. Ed., vol. 38(8) (Apr. 1999), 1093-1094.
Soucy, F., et al., “A Novel and Efficient Synthesis of a Highly Active Analogue of clasto-Lactacystin Beta-Lactone,” vol. 121 (43), pp. 9967-9976 (Nov. 1999).
Crane, S., and Corey, E., “A Novel Enantioselective Synthetic Route to Omuralide Analogues with the Potential for Species Selectivity in Proteasome Inhibition,” vol. 3(9), pp. 1395-1397 (2001).
Saravanan, P., and Corey, E., “A Short, Stereocontolled, and Practical Synthesis of Alpha-Methylomuralide, a Potent Inhibitor of Proteasome Function,” J. Org. Chem., vol. 68(7), pp. 2760-2764.
Corey Elias J.
Hogan Philip C.
Berch Mark L
President and Fellows of Harvard College
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