Drug – bio-affecting and body treating compositions – Radionuclide or intended radionuclide containing; adjuvant... – In an organic compound
Patent
1994-06-20
1996-11-12
Lovering, Richard D.
Drug, bio-affecting and body treating compositions
Radionuclide or intended radionuclide containing; adjuvant...
In an organic compound
A61K 5108
Patent
active
055737480
ABSTRACT:
The present invention is directed to novel radiopharmaceutical imaging agents incorporating Tc-99m as a radiolabel. In particular, the novel imaging agents disclosed herein have relatively high renal extraction efficiencies, and hence are useful for conducting renal function imaging procedures. The novel Tc-99m compounds of a present invention have the following general formula: ##STR1## wherein X is S or N; and wherein Y is H or wherein Y is ##STR2## and where R.sub.1 is --H, --CH.sub.3, or --CH.sub.2 CH.sub.3 ; R.sub.2 is --H, --CH.sub.2 CO.sub.2 H, --CH.sub.2 CONH.sub.2, --CH.sub.2 CH.sub.2 CO.sub.2 H, --CH.sub.2 CH.sub.2 CONH.sub.2, --CH.sub.3, --CH.sub.2 CH.sub.3, CH.sub.2 C.sub.6 H.sub.5, or --CH.sub.2 OH; and Z is --H, --CO.sub.2 H, --CONH.sub.2, --SO.sub.3 H, --SO.sub.2 NH.sub.2, or --CONHCH.sub.2 CO.sub.2 H; and the Tc is Tc-99m; and water-soluble salts thereof. Of the foregoing, the presently preferred Tc-99m compound of the present invention is Tc-99m-mercaptoacetylglycylglycylglycine (Tc-99m-MAGGG). The present invention is also directed to novel chelating agents that may be reacted with Tc-99m to form the foregoing compounds. Such novel chelating agents have the following general formula. ##STR3## where X and Y have the same definitions as above, and wherein Y' is --H.sub.2 when X is N, or wherein Y' is --H, or a suitable protective group such as --COCH.sub.3, --COC.sub.6 H.sub.5, --CH.sub.2 NHCOCH.sub.3, --COCF.sub.3, or --COCH.sub.2 OH when X is S. The present invention also provides methods for preparing and using the novel Tc-99m compounds.
REFERENCES:
patent: 3822509 (1974-07-01), Brown et al.
patent: 3830746 (1974-08-01), Brown
patent: 3912935 (1975-10-01), Harris
patent: 4048296 (1977-09-01), Wolfangel
patent: 4296785 (1981-10-01), Vittello et al.
patent: 4434151 (1984-02-01), Bryne et al.
patent: 4444690 (1984-04-01), Fitzberg
patent: 4615876 (1986-10-01), Troutner et al.
patent: 4670545 (1987-06-01), Fitzberg et al.
patent: 4849511 (1989-07-01), Verbruggen
patent: 4861869 (1989-08-01), Nicolotti et al.
patent: 4883862 (1989-11-01), Chervu et al.
patent: 4925650 (1990-05-01), Nosco et al.
patent: 4965392 (1990-10-01), Fritzberg et al.
patent: 4980147 (1990-12-01), Fritzberg et al.
patent: 5322929 (1994-06-01), Fritzberg et al.
Adibi, et al. "Enrichment of glycine pool in plasma . . .", Chem Abs. 97 (23) 196268p, Dec. 6, 1982.
Brubacher, et al., Biochem. Biophys Res. Comm., vol. 27, No. 2, pp. 176-182, 1967.
Chem. Abs . . . , vol. 61, No. 6, Abs. #8395e, Sep. 1964.
Chem. Abs . . . , vol. 70, No. 15, Abs. #68727t, 1969.
Chem. Abs . . . , vol. 90, No. 23, Abs #187323f, Jun. 1979.
Dorigatti, et al., J. Inorg. Nucl. Chem., vol. 37, pp. 1515-1520, 1975.
Fritzberg, et al., "Synthesis and Biological Evaluation of Tc-99m N,N'-Bis(mercaptoacetyl)-2, 3-diaminopropanoate: A Potential Replacement for (.sup.131)-iodohippurate" The Journal of Nuclear Medicine, Jul. 1982, vol. 23, No. 7.
Fritzberg, et al.,, "A Potential Tc-99m Renal Rubular Function Agent: Tc-99m-BIX-N,N'-(Mercaptoacetamido)-2,3-diaminoproponoate".
Fritzberg, et al., "Synthesis and Evaluation of N.sub.2 S.sub.2 Complexes of Tc-99m as Renal Function Agents", The Journal of Nuclear Medicine, vol. 25, p. 16, May 1984.
Fritzberg, "Current Status of Renal Radiopharmaceuticals", Journal of Nuclear Medicine Technology, vol. 12, No. 4, pp. 177-188, Dec. 1984.
Fritzberg, "Synthesis and Biological Evaluation of Technetium-99 MAG.sub.3 as a Hippuran Replacement", Journal of Nuclear Medicine, 27:1, pp. 111-116, Jan. 1986.
Klingensmith III, et al. "Clinical Comparison of Tc-99m n,N'-Bis (mercaptoacetamido) ethylenediamine and (.sup.131) ortho-iodohippurate for Evaluation of Renal Tubular Function: Concise Communication" The Journal of Nuclear Medicine, May 1982, vol. 23, No. 5, pp. 377-380.
Klingensmith III, et al., "Clinical Evaluation of Tc-99m N,N'-Bis (mercaptoacetyl)-2, 3-Diaminopropanoate as a Replacement for I-131 Hippurate: Concise Communication", The Journal of Nuclear Medicine, vol. 25, No. 1, 1984.
Mallinckrodt, Inc., Technical Product Data, "Hippuran rI 131 Injection Iodohippurate Sodium I 131 Injection Diagnostic-For Intravenous Use", R1/83 MK-20348 (Mallinckrodt, Inc., Diagnostic Products Division, St. Louis, MO 63134), 1983.
Nakahara, et al. "Reactions of Metal Chelates . . .", Chem. Abs. 69 (23), 97137k, 1968.
Nosco, et al., "Preparation and Evaluation of MAG.sub.3 -Like Compounds as Renal Agents", The Journal of Nuclear Medicine, vol. 30, No. 5 May 1989.
Nosco, et al., "Chemistry of Tc-MAG.sub.3 and Derivatives; Synthesis, Characterization, Reactivity and Biodistribution of these Complexes", The Journal of Nuclear Medicine, vol. 29, No. 5, May 1988.
Schneider, et al., "N,N'bis(S-Benzoylmercaptoacetamindo) Ethylenediamine and Propylenediamine Ligands as Renal Function Imaging Agents. 1. Alternate Synthetic Methods"The Journal of Nuclear Medicine, vol. 25, No. 2, 1984.
Schneider, "Alternate Synthesis and Evaluation of a Series of N,N-Bis(Mercaptoacetamido) Ethylenediamine and Propylenediamine Ligands as Renal Imaging Agents," Division of Nuclear Medicine; The Upstate Medical Center, 750 E. Adams Street, Syracuse, New York 13210, 1983.
Simic, et al. Radiation Research, vol. 48, pp. 244-255, 1971.
Sokol, "Detection of N-acetylglycylglycine . . .", Chem. Abs. 90 (22) 179658d, May 28, 1979.
Sudhakar, et al., "Tissue Distribution Properties of Technetium-99m-Diamide-Dimercaptide Complexes and Potential Use of Renal Radiopharmaceuticals", Journal of Medicinal Chemistry, 29, pp. 1933-1940, 1986.
Sugiura, Inorganic Chemestry, vol. 17, No. 8, pp. 2176-2182, 1978.
Sugiura, "Newly Synthesized Sulfhydryl-and Imidazole-Containing Tripeptides with a Specific Copper-Binding Site", Faculty of Pharmaceutic, Kyoto University, Kyoto. Received Dec. 15, 1977.
Verbruggen, et al., "Evaluation of the Diastereomers of Tc-99m-Mercaptoace-Tyglycyl-D-Alanylglycine (Tc-99m-D-Magag) in Primates", The Journal of Nuclear Medicine, vol. 29, No. 5, May 1988.
Verbruggen, et al., "Evaluation of the Renal Excretion Characteristics of Tc-99m-Mercaptoacetylglycyl-D-Serylglycine", The Journal of Nuclear Medicine, vol. 28, No. 4, Apr. 1987.
Yamane, et al. "Decarboxylation Reaction . . .", Chem. Abs. 86 (23) 171827e, Jun. 6, 1977.
Chapman Lara E.
Lovering Richard D.
University of Utah Research Foundation
LandOfFree
Radiolabeled technetium chelates for use in renal function deter does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Radiolabeled technetium chelates for use in renal function deter, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Radiolabeled technetium chelates for use in renal function deter will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-560505