Tumor imaging compounds

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Radical -xh acid – or anhydride – acid halide or salt thereof...

Reexamination Certificate

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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

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