Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Radical -xh acid – or anhydride – acid halide or salt thereof...
Reexamination Certificate
2003-04-24
2009-06-09
Zucker, Paul A (Department: 1621)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Radical -xh acid, or anhydride, acid halide or salt thereof...
C514S572000, C562S574000
Reexamination Certificate
active
07544715
ABSTRACT:
The invention provides novel amino acid compounds of use in detecting and evaluating brain and body tumors. These compounds combine the advantageous properties of α-aminoisobutyric acid (AIB) analogs namely, their rapid uptake and prolonged retention in tumors with the properties of halogen substituents, including certain useful halogen isotopes such as fluorine-18, iodine-123, iodine-124, iodine-125, iodine-131, bromine-75, bromine-76, bromine-77, bromine-82, astatine-210, astatine-211, and other astatine isotopes. In addition the compounds can be labeled with technetium and rhenium isotopes using known chelation complexes. The amino acid compounds disclosed herein have a high specificity for target sites when administered to a subject in vivo. The labeled amino acid compounds are useful as imaging agents in detecting and/or monitoring tumors in a subject by Positron Emission Tomography (PET) and Single Photon Emission Computer Tomography (SPECT).
REFERENCES:
patent: 3855208 (1974-12-01), Rutner et al.
patent: 4325961 (1982-04-01), Kollonitsch et al.
patent: 4358434 (1982-11-01), Tzodikov et al.
patent: 4390517 (1983-06-01), O'Brien et al.
patent: 4483870 (1984-11-01), Kollonitsch et al.
patent: 4695588 (1987-09-01), Kollonitsch et al.
patent: 4743691 (1988-05-01), Bey et al.
patent: 4760091 (1988-07-01), Carson et al.
patent: 4942231 (1990-07-01), Mertens
patent: 5227467 (1993-07-01), Kollonitsch et al.
patent: 5279812 (1994-01-01), Krstenansky et al.
patent: 5310912 (1994-05-01), Neumeyer et al.
patent: 5324504 (1994-06-01), Roger, Jr. et al.
patent: 5413779 (1995-05-01), Kuhar et al.
patent: 5637759 (1997-06-01), Hearst et al.
patent: 5698179 (1997-12-01), Neumeyer et al.
patent: 5808146 (1998-09-01), Goodman et al.
patent: 5817776 (1998-10-01), Goodman et al.
patent: 5853696 (1998-12-01), Elmaleh et al.
patent: 6344179 (2002-02-01), Goodman
patent: 6399042 (2002-06-01), Goodman
patent: 2002/0099184 (2002-07-01), Goodman
patent: WO 97/17092 (1997-05-01), None
patent: WO 97/43285 (1997-11-01), None
Alexoff, DL et al. (1992), “Ion Chromatographic Analysis of High Specific Activity18FDG Preparations and Detection of the Chemical Impurity 2-Deoxy-2-chloro-D-glucose”IInternat. J. Rad. Appl. Instr. Part A43(11):1313-1322.
Bergmann, ED et al. (1962), “Organic Fluorine Compounds. Part XXVII. Fluorinated α-Aminoisobutyric Acids”;J. Chem. Soc. 3462-3463.
Betz, AL et al. (1978), “Polarity of the Blood-Brain Barrier: Neutral Amino Acid Transport into Isolated Brain Capillaries”;Science202:225-227.
Bey, P et al.(1979), “Direct Synthesis of Alpha-Halogenomethyl-Alpha-Amino Acids from the Parent Apha-Amino Acids”;J. Org. Chem. 44(15):2732-2742.
Blough, BE et al. (1996), “Synthesis and Transporter Binding Properties of 3β-(4′-Alkyl-, 4′-alkenyl-, and 41-alkynylphenyl)nortropane-2β-carboxylic Acid Methyl Esters: Serotonin Transporter Selective Analogs”J. Med. Chem. 39(20):4027-4035.
Blough, BE et al. (1997), “3β-(4-Ethyl-3-iodophenyl)nortropane-2β-carboxylic Acid Methyl Ester as a High-Affinity Selective Ligand for the Serotonin Transporter”;J. Med. Chem. 40(24):3861-3864.
Bodsch et al. (1988), “Biochemical and Autoradiographic Study of Cerebral Protein Synthesis with Fluorine-18 Fluorophenylalanine and Carbon-14 Fluorophenylalanine”;J. Neurochemistry50(3):979-983.
Boger, DL et al. (1992), “Functional Analogs of CC-1065 and the Duocarmycins Incorporating the 9a-(Chloromethyl)-1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one (C2BI) Alkylation Sunbunit: Synthesis and Preliminary DNA Alkylation Studies”;J. Amer. Chem. Soc. 114:9318-9327.
Buonocore, E (1992), “Comparison Of PET With Conventional Imaging Techniques”;Clinical Positron Emission Tomography. Mosby-Year Book Inc. St. Louis, MO, pp. 17-22.
Bussolati, O et al. (1996), “The stimulation of Na, K, CI cotransport and of system A for neutral amino acid transport is a mechanism for cell volume increase during the cell cycle”;The FASEB Journal10:920-926.
Chiotellis, E et al. (1977), “Preparation of Tc-99m Labeled Pyridoxal-Amino Acid Complexes and their Evaluation”;Int. J. Nucl. Med. Biol. 4(1):29-41.
Christensen, HN et al. (1983), “Synthesis and Transport applications of 3-Aminobicyclo[3.2.1]octane-3-carboxylic Acids”;J. Med. Chem. 16:1374-1378.
Coleman, RE. (1991), “Single Photon Emission Computed Tomography and Positron Emission Tomography in Cancer Imaging”;Cancer67(4 suppl):1261-1270.
Conti, PS et al. (1986), “Tumor Imaging with Carbon-11 Labeled Alpha-Aminoisobutyric Acid (AIB) in a Patient with Advanced Malignant Melanoma”;Eur. J. Nucl. Med. 12:353-356.
Conti, PS (1995), “Introduction to Imaging Brain Tumor Metabolism with Positron Emmision Tomography (PET)”;Cancer Invest. 13(2):244-259.
Conti, PS et al. (1985), “Tumor localization of alpha-aminoisobutyric acid (AIB) in human melanoma heterotransplants”;Eur. J. Nucl. Med. 10:45-47.
Damhaut, P et al. (1997), “No-Carrier-Added Asymmetric Synthesis of Alpha-Methyl-Alpha-Amino Acids Labelled with Fluorine-18”;Tetrahedron53(16):5785-5796.
Di Chiro et al. (1982), “Glucose utilization of cerebral gliomas measured by [18F] Fluorodeoxyglucose and Positron Emission Tomography”;Neurology(NY) 32:1323-1329.
Dunzendorfer, U et al. (1981), “Synthesis and Body Distribution of Alpha-Aminoisobutyric Acid-L-11C in Normal and Prostate Cancer-Bearing Rat After Chemotherapy”;Eur. J. Nucl. Med. 6:535-538.
Dutta, AK et al. (1996), “Structure-Activity Relationship Studies of Novel 4-[2-[Bis(4-fluorophenyl)methoxy]ethyl]-1-(3-phenylproply-piperidine Analogs: Synthesis and Biological Evaluation at the Dopamine and Serotonin Transporter Sites”;J. Med. Chem. 39:749-756.
Feinendegen, LE (1993), “Contributions of Nuclear Medicine to the Therapy of Malignant Tumors (editorial)”;J. Can. Res. Clin. Oncol. 119(6):320-322.
Fischman, AJ et al. (1997), “SPECT Imaging of Dopamine Transporter Sites in Normal and MPTP-Treated Rhesus Monkeys”;J. Nucl. Med. 38:144-150.
Giros, B. et al. (1996), “Hyperlocomotion and indifference to cocaine and amphetamine in mice lacking the dopamine transporter”;Nature379:606-612.
Goodman, MM et al. (1994), “Synthesis and Characterization of Radioiodinated N-(3-Iodopropen-1-yl)-2β-carbomethoxy-3β-(4-chlorophenyl)tropanes: Potential Dopamine Reuptake Site Imaging Agents”;J. Med. Chem. 37:1535-1542.
Goodman, MM et al.Clinical Positron Emission TomographyMosby Year Book, 1992, K.F. Hubner, et al., Chapter 14 “Automated Synthesis of Radiotracers for PET Applications” pp. 110-122.
Griffeth, LK et al. (1993), “Brain Metastases from Non-Central Nervous System Tumors: Evaluation with PET”;Radiology186:37-44.
Hoyte, R et al. (1970), “Fluorine-18 Labeled Amino-Acids for Organic Imaging”;J. Nucl. Med. 11(10):633. (Abstract only).
Hume, SP et al. (1991), “Citalopram: Labelling with Carbon-11 and Evaluation in Rat as a Potential Radioligand for In Vivo PET Studies of 5-HT Re-uptake Sites”;Nucl. Med. Biol. 18:339-351.
Ishiwata et al. (1993), “Re-evaluation of Amino Acid PET Studies: Can the Protein Synthesis Rates in Brain and Tumor Tissues be Measured in Vivo?”J. Nucl. Med. 34(11):1936-1943.
Jager, PL et al. (2001), “Radiolabeled Amino Acids: Basic Aspects and Clinical Applications in Oncology”;Nucl. Med., 42:432-445.
Kilbourn, MR et al. (1989), “Synthesis of Radiolabeled Inhibitors of Presynaptic Monoamine Uptake Systems: [18F]GBR 13119(DA),[11C]Nisoxetine (NE), and [11C]Fluoxtine (5-HT)”J. Label. Cmpd. Radiopharm. 26:412-414. (Symposium Abstract).
Kollonitsch et al. (1975), “Selective Flourination of Hydroxy Amines and Hydroxy Amino-Acids with Sulfur Tetrafluoride in Liquid Hydrogen Fluoride”;J. Org. C
Goodman Mark M.
McConathy Jonathan
Emory University
Greenlee Winner and Sullivan P.C.
Zucker Paul A
LandOfFree
Tumor imaging compounds does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Tumor imaging compounds, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Tumor imaging compounds will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-4094337