Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2007-06-12
2007-06-12
Saeed, Kamal A. (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C548S338100
Reexamination Certificate
active
10297454
ABSTRACT:
Novel18F-flourine compounds useful for non-invasive imaging techniques such as PET, for detecting tissue hypoxia, and methods for preparing them are disclosed. Novel intermediate compounds and methods for preparing them are also disclosed. Diagnostic kits useful in practicing the methods of claimed invention are also provided.
REFERENCES:
patent: 3505349 (1970-04-01), Beaman et al.
patent: 5540908 (1996-07-01), Koch et al.
patent: 5721265 (1998-02-01), Tracy et al.
patent: 5843404 (1998-12-01), Koch et al.
patent: 6252087 (2001-06-01), Koch et al.
Adams, G.E., “Hypoxia-mediaed drugs for radiation and chemotherapy,”Cancer, 1981, 48(3), 696-707.
Castelhano, A.L., et al., “Reactions of an electrophilic glycine cation equivalent with grignard reagents a simple synthesis of β,δ—unsaturated amino acids,”Tetrahedron Letts., 1986, 27(22), 2435-2438.
Castelhano, A.L., et al., “Synthesis of α-amino acids with β, γ-unsaturated side chains,”Tetrahedron Letters, 1988, 44(17), 5451-5466.
Chapman, J.D., et al., “The fraction of hypoxic clonogenic cells in tumor populations,” inBiological Bases and Clinical Implications of Tumor Radioresistance, 1983, Fletcher, G.H., et al. (Eds.), 61-73.
Chapman, J.D., et al., “Keynote address: Cellular reduction of nitroimidazole drugs: potential for selective chemotherapy and diagnosis of hypoxic cells,”Int. J. Radiat. Oncol. Biol. Phys., 1989, 16, 911-917.
Evans, S.M., et al., “Noninvasive detection of tumor hypoxia using the 2-nitroimidazole [18F]EF1,”J. of Nuclear Medicine, 2000, 41, 327-336.
Franko, A.J., et al., “Oxygen dependence of binding of misonidazole to rodent and human tumorsin vitro,” Cancer Res., Oct. 15, 1987, 47, 5367-5376.
Grierson, J.R., et al., “A radiosynthesis of fluorine-18 fluoromisonidazole,”J. of Nuclear Medicine, Mar. 1989, 30(3), 343-350.
Jerabek, P.A., et al., “Synthesis and biodistribution of18F-labeled fluoronitroimidazoles: potentialin vivomarkers of hypoxic tissue,”Applied Radiation&Isotopes, 1986, 37(7), 599-605.
Kachur, A.V., et al., “Synthesis of new hypoxia markers EF1 and [18F]-EF1,”J. of Applied Radiation and Isotopes, 1999, 51(6), 643-650.
Kennedy, K.A., et al., “Commentary: The hypoxic tumor cell: a target for selective cancer chemotherapy,”Biochem. Pharm., 1980, 29, 1-8.
Koch, C.J., et al., “Metabolism induced binding of14C-misonidazole to hypoxic cells: kinetic dependence on oxygen concentration and misonidazole concentration,”Int. J. Radiation Oncology Biol. Phys., 1984, 10, 1327-1331.
Koch, C.J., “The reduction activation of nitroimidazoles; modification by oxygen and other redox-active molecules in cellular systems,”Selective Activation of Drugs by Redox Processes, Adams, G.E., et al (Eds.), 1990, 237-247.
Koch, C.J., “The mechanisms of radiation protection by non-protein sulfhydryls: glutathione, cysteine, and cysteamine,”CRC Press, 1998, 25-52.
Koh, W.-J., et al., “Postron emission tomography,”Acta Oncologica, 1994, 33(3), 323-327.
Koh, W.-J., et al., “Imaging of hypoxia in human tumors with [F-18]fluoromisonidazole,”International J. of Radiation Oncology, Biology Physics, 1991, 22, 199-212.
Mathias, C.J., et al., “Radiolabelled hypoxic cell sensitizers: tracers for assessment of ischemia,”Life Sciences, 1987, 41, 199-206.
Moulder, J.E., et al., “Hypoxic fractions of solid tumors: experimental techniques, methods of analysis, and a survey of existing data,”Int. J. Radioat. Oncol. Biol. Phys., 1984, 10, 695-712.
Ohah, G.A., et al., “Synthetic methods and reactions II. Halofluorination of alkenes in poly-hydrogen fluoride/pyridine solution,”Synthesis, Dec. 1973, 4, 780-783.
Pariament, M.B., et al., “None-invasive assessment of human tumour hypoxia with123I-idoazomycin arabinoside: preliminary report of clinical study,”Br. J. Cancer, 1992, 65, 90-95.
Raleigh, J.A., et al., “Fluorescence immunohistochemical detection of hypoxic cells in spheroids and tumours,”Br. J. Cancer, 1987, 56, 395-400.
Raleigh, J.A., et al., “Reductive fragmentation of 2-nitroimidazoles: amines and aldehydes,”Int. J. Radiat. Oncol. Biol. Phys., 1984, 10, 1337-1340.
Rasey, J.S., et al., “Characterization of [18F]fluoroetanidazole, a new radiopharmaceutical for detecting tumor hypoxia,”J. of Nuclear Medicine, Jun. 1999, 40(6), 1072-1079.
Rasey, J.S., et al., “Characterization of radiolabeled fluoromisonidazole as a probe for hypoxic cells,”Radiation Res., 1987, 111, 292-304.
Taylor, Y.C., et al., “Differences in toxicity and metabolism of the 2-nitromidazole misonidazole (Ro-07-0582) in hela and Chinese hamster ovary cells,”Cancer Res., 1978, 38, 2745-2752.
Tewson, T.J., “Synthesis of [18F]fluoroetanidazole: a potential new tracer for imaging hypoxia,”Nuclear Medicine&Biology, 1997, 24, 755-760.
Valk, P.E., “Hypoxia in human gliomas: demonstration by PET with fluorine-18-fluoromisonidazole,”J. Nucl. Med., 1992, 33, 2133-2137.
Varghese, A.J., et al., “Binding to cellular macromolecules as a possible mechanism for the cytotoxicity of misonidazole,”Cancer Res., Jul. 1980, 40, 2165-2169.
Williams, R.M., et al., “General synthesis of β,γ-alkynylglycine derivatives,”J. Org. Chem., 1990, 55, 4657-4663.
Yang, D.J., et al., “Development of F-18-labeled fluoroerythronitroimidazole as a PET agent for imaging tumor hypoxia,”Radiology, Mar. 1995, 194, 795-800.
Yeh, S.-H., et al., “fluorine-18 fluoromisonidazole tumour to muscle retention ration for the detection of hypoxia in nasopharyngeal carcinoma,”Europ. J. of Nuclear Medicine, Oct. 1996, 23(10), 1378-1383.
Copy of the Supplementary European Search Report dated Jun. 24, 2004 (EP 00 96 0168).
Walch, N.S., et al., “Mapping of the vascular endothelial growth factor-producing hypoxic cells in multicellular tumor spheroids using a hypoxia-specific marker,”Cancer Research, 1995, 55, 6222-6226.
Ido, T. et al., “Fluorination with F2-A Convenient Synthesis of 2-Deoxy-2-Fluoro-D-Glucose”,J. Org. Chem.,1977, 42(13), 2341-2342.
Dolbier William R
Kachur Alexander V
Koch Cameron J
Li An-Rong
Saeed Kamal A.
The Trustees of the University of Pennsylvania
Woodcock & Washburn LLP
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