Lapachone compounds and methods of use thereof

Details Lapachone compounds and methods of use thereof Lapachone compounds and methods of use thereof

2008-10-16

2011-11-29

Oh, Taylor V (Department: 1622)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

C514S434000, C549S010000, C549S016000

Reexamination Certificate

active

08067459

ABSTRACT:
The invention provides lapachone analogs and derivatives as well as methods of use thereof. These compounds can be used in pharmaceutical compositions for the treatment or prevention of cell proliferation disorders. These compounds can also be used in the treatment or prevention of cancer or precancerous conditions.

REFERENCES:
patent: 5763625 (1998-06-01), Boothman et al.
patent: 5824700 (1998-10-01), Frydman et al.
patent: 5969163 (1999-10-01), Frydman et al.
patent: 6245807 (2001-06-01), Pardee et al.
patent: 2002/0169135 (2002-11-01), Pardee et al.
patent: 2003/0091639 (2003-05-01), Jiang et al.
patent: 2004/0071775 (2004-04-01), Jiang et al.
patent: WO 94/04145 (1994-03-01), None
patent: WO 00/61142 (2000-10-01), None
patent: WO 03/011224 (2003-02-01), None
patent: WO 2004/045557 (2004-06-01), None
patent: WO 2004/045557 (2004-06-01), None
patent: WO 2007/139569 (2007-12-01), None
Banker and Rhodes, Modern Pharmaceutics, 2007, Marcel Dekker, Inc, 3rd Edition, p. 596.
‘Cancer Prevention Overview’, http://www.cancer.gov/cancertopics/pdq/prevention/overview/patient, accessed Apr. 9, 2010.
Golub et al., Molecular Classification of Cancer: Class Discovery and Class Prediction by Gene Expression Monitoring. Science, vol. 286, Oct. 15, 1999, p. 531-537.
‘Metabolite’, http://www.encyclopedia.com/doc/1E1-metabolit.html, accessed Jan. 25, 2008.
‘Prodrug’, http://www.medterms.com/script/main/art.asp?articlekey=23992, accessed Apr. 8, 2011.
Target Cancer Therapies, http://www.cancer.gov/cancertopics/factsheet/therapy/targeted,a accessed Jan. 12, 2011.
Voskoglou-Nomikos et al, Clincial Predictive Value of the in Vitro Cell line, Human Xenograft, and Mouse Allograft Preclinical Cancer Models, Sep. 15, 2003, Clnical Cancer Research, vol. 9, p. 4227-4239.
Pérez-Sacau et al., “Synthesis and pharmacophore modeling of naphthoquinone derivatives with Cytotoxic activity in human promyelocytic leukemia HL-60 cell line”,J. Med. Chem., 50(4):696-706 (2007).
Chuang et al., “Oxidative Free Radical Reaction of 2-Phenylthio-1,4-Naphthoquinones Initiated by Manganese(III) Acetate”,Heterocycles, 43(10):2215-2221 (1996).
Goncalves et al., “Evaluation of the Toxicity of 3-Allyl-β-Lapachone against Trypanosoma Cruzi Bloodsteam Forms”,Molecular and Biochemical Parasitology, 1:167-176 (1980).
Huang et al., “β-Lapachone Induces Cell Cycle Arrest and Apoptosis in Human Colon Cancer Cells”Molecular Medicine, 5:711-720 (1999).
Klapars et al., “Copper-Catalyzed Halogen Exchange in Aryl Halides: An Aromatic Finkelstein Reaction”,J. Am. Chem. Soc., 124:14844-14845 (2002).
Krapcho et al., “Heterosubstituted Anthracene-9,10-dione Analogues. The Synthesis and Antitimor Evaluation of 5,8-Bis[(aminoalkyl)amino]naptho[2,3-b]thiopene-4,9-diones”,J. Med. Chem., 33:2651-2655 (1990).
Kurokawa, “The Reaction of Cadalene and Eudalene with Sulfur”,Bulletin of the Chemical Society of Japan, 43:1454-1459 (1970).
Lai et al., “β-Lapachone Induced Cell Death in Human Hepatoma (HepA2) Cells”,Histol Histophatol, 13:89-97 (1998).
Li et al., “Induction of Apoptosis by β-Lapachone in Human Prostate Cancer Cells”,Cancer Research, 55:3712-3715 (1995).
Li et al., “Potent Induction of Apoptosis by β-Lapachone in Human Multiple Myeloma Cell Lines and Patient Cells”,Molecular Medicine, 6(12):1008-1015 (2000).
Li et al., “Potent Inhibition of Tumor Survival in vivo by β-Lapachone Plus Taxol: Combining Drugs Imposes Different Artificial Checkpoints”,PNAS, 96:13369-13374 (1999).
Li et al., “Release of Mitochondrial Cytochrome C in both Apoptosis and Necrosis Induced by β-Lapachone in Human Carcinoma Cells”,Molecular Medicine, 5:232-239 (1999).
Li et al., “Selective Killing of Cancer Cells by β-Lapachone: Direct Checkpoint Activation as a Strategy against Cancer”,PNAS, 100(5):2674-2678 (2003).
Li et al., “β-Lapachone, a Novel DNA Topoisomerase I Inhibitor with a Mode of Action Different from Camptothecin”,The Journal of Biological Chemistry, 268(30):22463-22468 (1993).
Planchon et al., “β-Lapachone-Mediated Apoptosis in Human Promyelocytic Leukemia (HL-60) and Human Prostate Cancer Cells: A p53-independent Response”,Cancer Research, 55:3706-3711 (1995).
Portela et al., “Redox Cycling of β-Lapachone and Related o-Naphthoquinones in the Presence of Dihydrolipoamide and Oxygen”,Biochemical Pharmacology, 51:275-283 (1996).
Prieto et al., “Arylboronic Acids and Arylpinacolboronate Esters in Suzuki Coupling Reactions Involving Indoles. Partner Role Swapping and Heterocycle Protection”,J. Org. Chem., 69:6812-6820 (2004).
Schaffner-Sabba et al., “β-Lapachone: Synthesis of Derivatives and Activities in Tumor Models”,J. Med. Chem., 27:990-994 (1984).
Suginome et al., “One-Step Synthesis of 2,3-Dihydronaphtho[2,3-b]thiophene-4,9-diones by a New Regioselective [3+2] Photoaddition of Photogenerated 2-Mercapto-1,4-naphthoquinone with Alkenes”,J. Chem. Soc., Chem. Commun., 807-809 (1993).
Tapia et al., “Synthesis of 2H-Naphtho[2,3-b]Thiopyranoquinones and Density Functional Study for the Diels-Alder Reaction of a Benzothiopyranoquinone”,Heterocycles, 53(3):585-598 (1999).
Tapia et al., “Synthesis of 3,4-Dihydro-4-hydroxy-9-methoxy-2H-naphtho[2,3-b]thiopyranoquinone”,Tetrahedron Letters, 38(1):153-154 (1997).
Tonholo et al., “Electrochemical Properties of Biologically Active Heterocyclic Naphthoquinones”,J. Braz. Chem. Soc., 9(2):163-169 (1998).
Weller et al., “Topoisomerase-I Inhibitors for Human Malignant Glioma: Differential Modulation of p53, p21, bax and bcl-2 Expression and of CD95-Mediated Apoptosis by Camptothecin and β-Lapachone”,Int. J. Cancer, 73:707-714 (1997).
Wuerzberger et al., “Induction of Apoptosis in MCF-7:WS8 Breast Cancer Cells by β-Lapachone”,Cancer Research, 58:1876-1885 (1998).
Sugiyama et al., “Aldose reductase catalyzed the oxidation of naphathalene-1,2-dihydrodiol for the formation of ortho-naphthoquinone”,Drug Metab. Disposition, 27(1):60-67 (1999).

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