Hypoxia-selective, weakly basic 2-nitroimidazole delivery...

Details Hypoxia-selective, weakly basic 2-nitroimidazole delivery... Hypoxia-selective, weakly basic 2-nitroimidazole delivery...

2006-10-27

2010-11-30

Jones, D L (Department: 1618)

Drug, bio-affecting and body treating compositions

Radionuclide or intended radionuclide containing; adjuvant...

In an organic compound

C424S001110, C424S001810, C424S001850, C424S001890, C548S300100, C548S327100, C548S327500

Reexamination Certificate

active

07842278

ABSTRACT:
The invention features a class of 2-nitroimidazole compounds with a secondary basic nitrogen atom and a linker bearing one or more therapeutic agents, cytotoxic agents, detectable labels, or chelating groups. In particular, the invention provides 2-nitroimidazole compounds containing a cluster of boron atoms for use in boron neutron capture therapy (BNCT). The 2-nitroimidazole compounds can be used to treat hypoxic conditions, including, e.g., cancer, inflammation, and ischemia. The weakly basic 2-nitroimidazole compounds target to hypoxic tissue and provide increased tissue concentration overall.

REFERENCES:
patent: 4282232 (1981-08-01), Agrawal
patent: 5387692 (1995-02-01), Riley et al.
patent: 5674693 (1997-10-01), Raleigh et al.
patent: 2008/0085237 (2008-04-01), Raleigh et al.
patent: 0 302 416 (1989-02-01), None
patent: WO 2008/063749 (2008-05-01), None
Naylor et al, Journal of Medicinal Chemistry, 1990, vol. 33, No. 9, pp. 2508-2513.
Barth et al., “Boron Neutron Capture Therapy for Cancer. Realities and Prospects,”Cancer70: 2995-3007, 1992.
Barth et al., “Boron Neutron Capture Therapy of Brain Tumors: An Emerging Therapeutic Modality,”Neurosurgery44: 433-450, 1999.
Barth et al., “Boron Neutron Capture Therapy of Cancer: Current Status and Future Prospects,”Clin. Cancer Res. 11: 3987-4002, 2005.
Bonnett, “Photosensitizers of the Porphyrin and Phthalocyanine Series for Photodynamic Therapy,”Chem. Soc. Rev. 24: 19-33, 1995.
Capala et al., “Accumulation of Boron in Malignant and Normal Cells Incubated in Vitro with Boronophenylalanine, Mercaptoborane or Boric Acid,”Radiat. Res. 146: 554-560, 1996.
Elowitz et al., “Biodistribution of p-Boronophenylalanine in Patients with Glioblastoma Multiforme for Use in Boron Neutron Capture Therapy,”Neurosurgery42: 463-469, 1998.
Gupta et al., “Common Challenges and Problems in Clinical Trials of Boron Neutron Capture Therapy of Brain Tumors,”J. Neurooncol. 62: 197-210, 2003.
Hodgkiss, “Use of 2-Nitroimidazoles as Bioreductive Markers for Tumour Hypoxia,”Anti-Cancer Drug Design13: 687-702, 1998.
Kageji et al., “Pharmacokinetics and Boron Uptake of BSH (Na2B12H11SH) in Patients with Intracranial Tumors,”J. Neurooncol. 33: 117-130, 1997.
Kahl et al., “Synthesis of Tetrakis-Carborane-Carboxylate Esters of 2,4-bis-(α, β-Dihydroxyethyl)-Deuteroporphyrin IX,”J. Chem. Soc., Chem. Commun. 1769-1771, 1990.
Locher, “Biological Effects and Therapeutic Possibilities of Neutrons,”American Journal of Roentgenology and Radium Therapy36: 1-13, 1936.
Matsumura et al., “A New Boronated Porphyrin (STA-BX909) for Neutron Capture Therapy: An in Vitro Survival Assay and in Vivo Tissue Uptake Study,”Cancer Lett. 141: 203-209, 1999.
Miura et al., “Preparation of Carboranyl Porphyrins for Boron Neutron Capture Therapy,”Tetrahedron Letters31: 2247-2250, 1990.
Pignol et al., “Selective Delivery of10B to Soft Tissue Sarcoma Using10B-L-Borophenylalanine for Boron Neutron Capture Therapy,”Br. J. Radiol. 71: 320-323, 1998.
Sasai et al., “Fluorinated 2-Nitroimidazole Derivative Hypoxic Cell Radiosensitizers: Radiosensitizing Activities and Pharmacokinetics,”Int. J. Radiat. Oncol. Biol. Phys. 29: 579-582, 1994.
Scobie et al., “Tumour-Targeted Boranes. 4. Synthesis of Nitroimidazole-Carboranes with Polyether-Isoxazole Links,”J. Org. Chem. 59: 7008-7013, 1994.
Scobie et al., “Tumour-Targeted Boranes. Part 3. Synthesis of Carbamate-Linked Nitroimidazolyl Carboranes Designed for Boron Neutron Capture Therapy of Cancer,”J. Chem. Soc., Perkin Trans. 1 2059-2063, 1994.
Soloway et al., “The Chemistry of Neutron Capture Therapy,”Chem. Rev. 98: 1515-1562, 1998.
Sugie et al., “Reevaluation of the Radiosensitizing Effects of Sanazole and Nimorazole in Vitro and in Vivo,”J. Radiat. Res. 46: 453-459, 2005.
Swenson et al., “Synthesis and Evaluation of a Boronated Nitroimidazole for Boron Neutron Capture Therapy,”J. Med. Chem. 39: 1540-1544, 1996.
Tolpin et al., “Synthesis and Chemistry of Mercaptoundecahydro-closo-dodecaborate (2-),”Inorganic Chemistry17: 2867-2873, 1978.
Wood et al., “Uptake and Retention of Nitroimidazole-Carboranes Designed for Boron Neutron Capture Therapy in Experimental Murine Tumours: Detection by11B Magnetic Resonance Spectroscopy,”International Journal of Radiation Biology70: 587-592, 1996.
Ali et al., “Metal Complexes as Photo- and Radiosensitizers,” Chem. Rev. 99:2379-2450.
Bormans et al., “Synthesis, Radio-LC-MS Analysis and Biodistribution in Mice of99mTc-NIM-BAT,” J. Label. Compds Radiopharm. 46:575-585, 2003.
Papadopoulou et al., “Synthesis of Novel 2-Nitroimidazole-Tethered Tricyclic Quinolines, Bearing a Second Heteroatom, and their in Vitro Evaluation as Hypoxia-Selective Cytotoxins and Radiosensitizers,” Bioorg. Med. Chem. Letters 14:1523-1525, 2004.
Papadopoulou et al., “Synthesis of Novel 2-Nitroimidazole-Spermidine Derivative as a Tumor-Targeted Hypoxia-Selective Cytotoxin,” Bioorg. Med. Chem. Letters 14:1519-1522, 2004.
Supplementary European Search Report from EP 07 87 1243, dated Nov. 23, 2009.
Ali et al., “Metal complexes as photo- and radiosensitizers,”Chem. Rev. 99:2379-2450, 1999.

Affiliated with

Also associated with

Rating

Hypoxia-selective, weakly basic 2-nitroimidazole delivery... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Hypoxia-selective, weakly basic 2-nitroimidazole delivery..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Hypoxia-selective, weakly basic 2-nitroimidazole delivery... will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-4251786