Drug – bio-affecting and body treating compositions – In vivo diagnosis or in vivo testing – Magnetic imaging agent
Patent
1989-07-31
1992-05-26
Raymond, Richard L.
Drug, bio-affecting and body treating compositions
In vivo diagnosis or in vivo testing
Magnetic imaging agent
424 5, 436173, 514 23, 514759, 536 11, 536 184, G01N 3100, G01N 2400, C07H 100, C07H 1500
Patent
active
051165996
ABSTRACT:
Accordingly, the present invention is directed to biological compounds derivatized so as to contain at least one perfluoro-t-butyl moiety for use in fluorine-19 NMR and/or MRI studies. The perfluoro-t-butyl (PFTB) moiety, ##STR1## is an excellent reporter group for fluorine-19 NMR/MRI. It is a source of nine magnetically equivalent fluorine nuclei which generate a single intense resonance for easy detection in spectroscopy or imaging. This signal is a sharp singlet, not split by neighboring nuclei or spread over a wide frequency range and eliminates any chance of ghost images which might arise from multiple resonances. These spectral properties ensure a maximum signal-to-noise ratio (S/N) for readily detecting this moiety. The foregoing allows either reduction in the concentration of the derivatized compound, ability to use MRI instruments with lower field strengths, a reduction in imaging times, or a combination of the foregoing as a result of this moiety producing a single, sharp, intense resonance.
REFERENCES:
patent: 3911138 (1975-10-01), Clark, Jr.
patent: 4105798 (1978-08-01), Moore et al.
patent: 4284558 (1981-09-01), Barton et al.
patent: 4325972 (1982-04-01), Geyer et al.
patent: 4558279 (1985-12-01), Ackerman et al.
patent: 4612185 (1986-09-01), Dean
patent: 4640833 (1987-02-01), Tamborski et al.
patent: 4775522 (1988-10-01), Clark
patent: 4820505 (1989-04-01), Ginsberg et al.
Smart, B. E. et al., Stable Perfluoroalkyl Carbanion Salts, J Am Chem Soc, 108:4905-4907 (1986).
Weigert, F. J. & Mahler, W., NMR Parameters of the Individual Fluorines of the Trifluoromethyl Group, J Am Chem Soc, 94:5314-5318 (1972).
Huang, H. N. et al., Synthesis of Owusoal Perfluorocarbon etters and amines containing bulk Perfluorocarbon groups: New Biomedical Materials, J Org Chem, 53:78-85 (1988).
Gopal B. Saha, Fundamentals of Nuclear Pharmacy (2nd Ed.), Springer-Verlag New York, Inc. (C) 1984, pp. 87-97 (Methods of radioiodination), pp. 116-118 (radioiodine labeled albumin, cholestrol and fibrinogen).
C. A. Otto et al., "Radiochemistry and Radiopharmaceuticals," J. Nucl. Med., 22:613-618, 1981 (radioiodinated fatty acids).
Principles of Radiopharmacology, vol. 1, CRC Press, Inc. Boca Raton, FL (Editor: Lelio G. Colombetti, Sc.D.) (C) 1979, pp. 30-35 and 40-43 (labeling techniques), pp. 193-206, 208-217, 221, 223-224, and 227-250 (various halogenated compounds, e.g. amino acids at pp. 211-212, sugars at p. 213, fatty acids at p. 213, and steroids at p. 228).
Whitmore, Organic Chemistry, D. Van Nostrand Company, Inc., N.Y., N.Y. (C) 1937, pp. 548-579 (Carbohydrates, Glucocides, Saccharides) 520-547 not provided.
Morrison & Boyd, Organic Chemistry (2nd Ed.), Allyn & Bacon, Inc., (C) 1966, pp. 708-709.
N. N. Becker et al., Abstracts 7th Annual Meeting Soc. Magn. Reson. Med., p. 447 (1988).
B. L. Dyatkin et al., Russian Chemical Reviews, vol. 45, No. 7, pp. 607-614 (1976) (translated from Uspekhi Khimii, vol. 45, pp. 1205-1221 (1976)).
G. N. Holland et al., J. Magn. Reson., vol. 28. pp. 133-136 (1977).
I. L. Knunyants et al., Synthesis of Fluoroorganic Compounds, Springer-Verlag, N.Y., pp. 5 and 12 (1985).
E. McFarland et al., J. Comput. Assist. Tomogr., vol. 9, No. 1, pp. 8-15 (Jan./Feb. 1985).
J. Weichert et al., Abstracts 7th Annual Meeting Soc. Magn. Reson. Med., p. 484 (1988).
Weichert et al., Abstracts 8th Annual Meeting Soc. Magn. Reson. Med., p. 330 (1989; after filing date).
A. M. Wyrwicz et al., J. Magn. Reson., vol. 69, No. 3, pp. 572-575 (Oct. 1, 1986).
Y. V. Zeifman et al., Russian Chemical Reviews, vol. 53, No. 3, pp. 256-273 (1984) (translated from Uspekhi Khimii, vol. 53, pp. 431-461 (1984)).
D. Eidelberg et al., ".sup.19 F NMR Imaging of Blood Oxygenation in the Brain," Magnetic Resonance in Medicine, vol. 6, pp. 344-352 (1988).
K. Yamada et al., "In vivo F-19 NMR Imaging and the Influence of Oxygenation on Relaxation Time", Sci. Rep. Res. Inst. Tohoku Univ., -C, vol. 33, Nos. 1-4, pp. 44-48 (1986).
J. Fraham et al., "Localized Proton NRM Spectroscopy in Different Regions of the Brain in Vivo. Relaxation Times and Concentrations of the Cerebral, Metabolites", Magnetic Resonance in Medicine, vol. 11, pp. 47-63 (1989).
D. M. Freeman et al., "Rapid .sup.19 F Magentic Resonance Imaging of Perfluorooctyl Bromide In Vivo", Magnetic Resonance Imaging, vol. 6, pp. 61-64, 1988.
R. L. Nunnally et al., "Flourine-19 NMR Spectroscopy and Imaging Investigations of Myocardial Perfusion and Cardiac Function", Magnetic Resonance Imaging, vol. 3, pp. 339-405, 1985.
W. M. Chew et al., "Spin-Echo Fluorine Magnetic Resonance Imaging at 2T: In Vivo Spatial Distribution of Halothane in the Rabbit Head", Magnetic Resonance Imaging, vol. 5, pp. 51-56, 1987.
T. Nakada et al., "F-19 NMR Imaging of Glucose Metabolism in the Rabbit", Radiology, vol. 168, pp. 823-825, 1988.
A. V. Ratner et al., "Detection of Tumors with .sup.19 F Magnetic Resonance Imaging", Investigative Radiology, vol. 23, pp. 361-364, May 1988.
M. E. Phelps, "Emission Computed Tomography", Seminars in Nuclear Medicine, vol. 7, No. 4, Oct. 1977.
M. E. Phelps et al., "ECAT: A New Computerized Tomographic Imaging System for Positron-Emitting Radiopharmaceuticals", The Journal of Nuclear Medicine, vol. 19, No. 6, pp. 635-647, 1978.
Amersham Corp. Technical Brochure: "Introduction to SPECT Brain Imaging with Ceretec.TM. (technetium Tc99m exametazime injection)", Printed Apr. 1989.
Medi-Physics, Inc. Technical Brochure: "SPECTamine.RTM. Iofetamine HCl I123 Injection", Issued Dec. 1987, .COPYRGT.1988.
Abstract, vol. 79, 1973, p. 408; Abstract No. 4760b.
Everett Thomas S.
Rogers, Jr. Walter J.
Hollinden Gary E.
Johns Hopkins Univ.
Raymond Richard L.
Towson State Univ.
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