Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2006-01-24
2006-01-24
Raymond, Richard (Department: 1623)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C424S009362, C424S009610, C514S185000, C514S410000, C534S015000
Reexamination Certificate
active
06989443
ABSTRACT:
The present invention is directed to low toxicity boronated compounds and methods for their use in the treatment, visualization, and diagnosis of tumors. More specifically, the present invention is directed to low toxicity carborane-containing 5, 10, 15, 20-tetraphenylporphyrin compounds and methods for their use particularly in boron neutron capture therapy (BNCT) and photodynamic therapy (PDT) for the treatment of tumors of the brain, head, neck, and surrounding tissue. The invention is also directed to using these carborane-containing tetraphenyl porphyrin compounds to methods of tumor imaging and/or diagnosis such as MRI, SPECT, or PET.
REFERENCES:
patent: 4783529 (1988-11-01), Lavallee et al.
patent: 4959356 (1990-09-01), Miura et al.
patent: 5149801 (1992-09-01), Kahl et al.
patent: 5162231 (1992-11-01), Cole et al.
patent: 5268371 (1993-12-01), Mauclaire et al.
patent: 5312896 (1994-05-01), Bhardwaj et al.
patent: 5563132 (1996-10-01), Bodaness
patent: 5654423 (1997-08-01), Kahl et al.
patent: 5674467 (1997-10-01), Maier et al.
patent: 5877165 (1999-03-01), Miura et al.
patent: 5955586 (1999-09-01), Sessler et al.
patent: 6010805 (2000-01-01), Scanlon, Jr. et al.
patent: 6066628 (2000-05-01), Stojiljkovic et al.
patent: 6566517 (2003-05-01), Miura et al.
patent: 2003/0032799 (2003-02-01), Miura et al.
patent: 2003/0083494 (2003-05-01), Miura et al.
patent: WO 01/85736 (2001-11-01), None
Harth et al. The Effect of Macromolecular Architecture in Nanomaterials: A comparison of Site Isolation in PolyphyrinCore Dedrimers and Their Isomeric Linear Analogues. J. Am. Chem Soc. 2002, 124, pp. 3926-3938.
Morris et al., “Porphyrin-mediated boron-neutron capture therapy: evaluation of the reactions of skin and central nervous system,”Int. J. Radiat. Biol.,79(3): 149-158 (2003).
Vincente, et al., “Synthesis, dark toxicity and induction of in vitro DNA photodamage by a tetra (4-nido-carboranylphenyl)prophyrin,”J. Photochem. Photobiol. B, Biology,68(2-3): 123-132 (2002).
Maderna et al., “Synthesis of a porphyrin-labelled carboranyl phosphate diester: a potential new drug for boron neutron capture therapy of cancer,”Chem. Commun.,16: 1784-1785 (2002).
Miura et al., “Boron Neutron Capture of a Marine Mammary Carcinoma using a Lipophilic Carboranyltetraphenylporphyrin,”Radiat. Res.,155(4): 603-610 (2001).
Miura et al., “Evaluation of carborane-containing porphyrins as tumor targeting agents for boron neutron capture therapy,”Br. J. Radiol.,71(847): 773-781 (1998).
Miura et al., “Synthesis of a Nickel Tetracarboranyltetraphenylporphyrin for Boron Neutro-Capture Therapy: Biodistribution and Toxicity in Tumor-Bearing Mice,”Int. J. Cancer.,68(1): 114-119 (1996).
Kahl et al., “A Carboranyl Porphyrin for Boron Neutron Capture Therapy of Brain Tumors,”Basic Life Sci.,50: 193-203 (1989).
Miura et al., “Biodistribution of copper carboranyltetraphenylporphyrins in rodents bearing an isogeneic or human neoplasm,”J. NeuroOncol,5,: 111-117 (2001).
Berlin et al., “Are Porphyrin Mixtures Favorable Photodynamic Anticancer Drugs? A Model Study with Combinatorial Libraries of Tetraphenylporphyrins,”Combinatorial Chemistry, 61(2): 107-118 (1998).
Miller et al., “In Vivo Animal Studies with Gadolinium (III) Texaphyrin As a Radiation Enhancer,”Int. J. Radiat. Oncol. Biol. Phys.,45(4): 981-989 (1999).
Bhyrappa et al., “Octabromotetraphenylporphyrin and Its Metal Derivatives: Electronic Structure and Electrochemical Properties,”Inorg. Chem.,30: 239-245 (1991).
Birnbaum et al.,n19F NMR Spectra and Structures of Halogenated Porphyrins,Inorg. Chem.,34(14): 3625-3632 (1995).
Fairchild et al., “Current Status of10B-Neutron Capture Therapy: Enhancement of Tumor Dose Via Beam Filtration and Dose Rate, and the Effects of These Parameters on Minimum Boron Content: a Theoretical Evaluation,”Int. J. Radiat. Oncol. Biol. Phys.,11(4): 831-840 (1985).
Woller et al., “2, 3, 7, 8, 12, 13, 17, 18-Octafluoro-5, 10, 15, 20-tetraarylporphyrins and Their Zinc Complexes: First Spectroscopic, Electrochemical, and Structural Characterization of a Perfluorinated Tetraarylmetalloporphyrin,”J. Org. Chem.,62(6): 1588-1593 (1997).
Woller et al., “A Straightforward Synthesis of 3,4-Difluoropyrrole,”J. Org. Chem.,63(6): 5706-5707 (1998).
Ozette et al., “New Metalloporphyrins with Extremely Altered Redox Properties: Synthesis, Structure, and Facile Reduction to Air-Stable n-Anion Radicals of Zinc and Nickel β-Heptanitroporphyrins,”J. Am. Chem. Soc.,119(27): 6442-6443 (1997).
Chanana et al., “Boron Neutron Capture Therapy for Glioblastoma Multiforme: Interim Results from the Phase I/II Dose-Escalation Studies,”Neurosurgery, 44(6): 1182-1193 (1999).
Vincente et al., “Synthesis of carbon—carbon linked carboranylated porphyrins for boron neutron capture therapy of cancer.”Tetrahedron Letters, 41: 7623-7627 (2000).
Evstigneeva, “Synthesis of Carboranylporphyrins and the Perspectives of Their Use for Boron Neutron Capture Therapy,”Molecules,5: 1479-80.
Zakharkin et al., “Synthesis of carboranyl derivatives of deuteroporphyrin 1X,”Russian Chemical Bulletin, 48(12): 2312-14 (1999).
“Brain Tumor Patients offered New Hope with Expanded Trial of Promising Therapy,” Press Release, Brookhaven National Labs, Nov. 1998, <http://virtualtrials.com/bnct2.cfm,>.
Yarris, “Accelerator for Boron Neutron Capture Therapy Proposed by Lab,” Jun. 21, 1996, Lawrence Berkeley National Laboratory, <http://www.lbl.gov/Science-Articles/Archive/boron-capture.html>.
Gomez, “Boron Neutron Capture Therapy (BNCT),” Dec. 1, 1998, Lawrence Berkeley National Laboratory, <http://www.virtualtrials.com/bnct.cfm>.
Chu et al., Overview—LBNL/UCSF Boron Neutron Capture Proposal, <http://ehs.lbl.gov/bnct/overview.html>.
Chu et al., Work In Progress—LBNL/UCSF Boron Neutron Capture Proposal, “Progress Report (Apr. 1997) on ‘Accelerator-Based BNCT Clinical Trial’,” <http://ehs.lbl.gov/bnct/progress.html>.
Ludewigt et al., “Research Topics and Papers, Neutron Production target for the BNCT Project at Lawrence Berkeley National Laboratory and at the University of California at San Francisco, Project 2b—Neutron Production Target,” <http://ehs.lbl.gov/bnct/research/target.html>.
Larson et al., “Research Topics and Papers, Phase I Study Concept for the BNCT Project at Lawrence Berkeley National Laboratory and at the University of California at San Francisco, Project 11—Proposed BNCT Clinical Trials,” <http://ehs.lbl.gov/bnct/research/proposedtrials.html>.
Deen et al, “Research Topics and Papers, Small Animal and In Vitro Toxicity and Biodistribution for the BNCT Project at Lawrence Berkeley National Laboratory and at the University of California at San Francisco, Project 6- Small Animal and In Vitro Toxicity, Biodistribution and Radiobiology,” http://ehs.lbl.gov/bnct/research/smallanimal.html>.
Fike et al, “Research Topics and Papers, Small Animal and In Vitro Toxicity and Biodistribution for the BNCT Project at Lawrence Berkeley National Laboratory and at the University of California at San Francisco, Project 7-Large Animal Pharmacology and Toxicology,” http://ehs.lbl.gov/bnct/research/largeanimal.html>.
Miura Michiko
Wu Haitao
Bogosian Margaret C.
Brookhaven Science Associates LLC
Fedowitz Matthew L.
Raymond Richard
LandOfFree
Carboranylporphyrins and uses thereof does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Carboranylporphyrins and uses thereof, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Carboranylporphyrins and uses thereof will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3524820