Drug – bio-affecting and body treating compositions – Radionuclide or intended radionuclide containing; adjuvant... – In an organic compound
Patent
1998-07-16
1999-11-09
Dees, Jose' G.
Drug, bio-affecting and body treating compositions
Radionuclide or intended radionuclide containing; adjuvant...
In an organic compound
424 111, 424 137, 424 91, 424 145, 534 14, 546124, 546132, 514304, A61K 5100, A61M 3614
Patent
active
059808608
ABSTRACT:
This invention presents a series of novel tropane-based derivatives complexed with either technetium or rhenium that are specific for central nervous system receptors, in particular, dopamine or serotonin receptors. The compounds of the invention have utility, inter alia, as imaging agents for CNS receptors. Methods of using these novel compounds as imaging agents are presented, as are intermediates and methods for making these novel compounds
REFERENCES:
patent: 5128118 (1992-07-01), Carroll et al.
patent: 5298499 (1994-03-01), Carroll et al.
patent: 5380848 (1995-01-01), Kuhar et al.
patent: 5413779 (1995-05-01), Kuhar et al.
patent: 5496953 (1996-03-01), Kuhar et al.
patent: 5700446 (1997-12-01), Neumeyer et al.
patent: 5736123 (1998-04-01), Carroll
patent: 5736556 (1998-04-01), Moldt et al.
patent: 5750089 (1998-05-01), Neumeyer et al.
Carroll, F.I. et al., "Synthesis, ligand binding, and QSAR (CoMFA and classical) study of 3 beta-(3'-substituted phenly)-, 3 beta-(4'-substituted phenyl)-, and 3 beta-(3',4'-disubstituted phenyl)tropane-2 beta-carboxylic acid methyl esters," J. Med. Chem. 37:2865-2873 (1994).
Carroll, F.I. et al., "Development of Imaging Agents for the Dopamine Transporter," Medicinal Res. Rev. 15:419-444 (Sep. 1995).
Carroll, F.I. et al., "Cocaine and 3-.beta.-(4'-substituted phenyl) tropane-2.beta.-carboxylic acid ester and amide analogues. New high-affinity and selective compounds for the dopamine transporter," J. Med. Chem. 38:379-388 (Jan. 1995).
Chi, D.Y. et al., "Homodimeric and Heterodimeric Bis (amino thiol) Oxometal Complex Formation and an Approach to Metal Complexes that Mimic Steroid Hormones," J. Med. Chem. 37:928-935 (1994).
Chi, D.Y. et al., "Selective Formation of Heterodimeric Bis-Cidentate Aminothiol--Oxometal Complexes of Rhenium (V)," J. Amer. Chem. Soc. 115:7045-7046 (1993).
Clarke, R.L. et al., "Compounds affecting the central nervous system. 4.3 Beta-phenyltropane-2-carboxylic esters and analogs," J. Med. Chem. 16:1260-1267 (1973).
Clarke, R.L. et al., "(2-exo-3-endo)-2-Aryltropane-3-carboxylic esters, a new class of narcotic antagonists," J. Med. Chem. 21:1235-1242 (1978).
Del Rosario, R. et al., "Synthesis and In Vivo Evaluation of a .sup.99m/99 Tc-DADT-benzovesamicol: a potential marker for cholinergic neurons," Nucl. Med. Biol. 21:197-203 (1994).
Dhar, T.G. et al., "Design, Synthesis and Evaluation of Substituted Triarylnipecotic Acid Derivatives as GABA Uptake Inhibitors: Identification of a Ligand with Moderate Affinity and Selectivity for the Cloned Human GABA Transporter GAT-3," J. Med. Chem. 37:2334-2342 (1994).
DiZio, J. et al., "Progestin-Rhenium Complexes: Metalabeled Steroids with High Receptor Binding Affinity, Potential Receptor-Directed Agents for Diagnostic imaging or therapy," Bioconjug. Chem. 2:353-366 (1991).
DiZio, J. et al., "Technetium and Rhenium-Labeled Progestine: Synthesis, Receptor Binding and In Vivo Distribution of an 11-.alpha.-Substituted Progestin Labeled with Technetium-99 and Rhenium-186," J. Nucl. Med. 33:558-569 (1992).
Eckelman, W.C. et al., "The Status of Radiopharmaceutical Research," Nucl. Med. Biol. 18:iii-vi (1991).
Fowler, J.S. et al., "Chapter 29. New Directions in Positron Emission Tomography," In: Annu. Reports in Medicinal Chemistry, pp. 277-286 (1989).
Fowler, J.S. et al., "Chapter 28. New Directions in Positron Emission Tomography--PartII," In:Annu. Rep. Medicinal Chem., pp. 261-289 (1990).
Fowler, J.S. et al., "Comparative PET studies of the kinetics and distribution of cocaine and cocaethylene in baboon brain," Synapse 12:220-227 (1992).
Frost, J.J. et al., "Positron Emission Tomographic Imaging of the Dopamine Tranporter with .sup.11 C-WIN 35, 428 Reveals Marked Declines in Mild Parkinson's Disease," Ann. Neurol. 34:423-431 (1993).
Goodman, M.M. et al., "Synthesis and characterization of radioiodinated N-(3-iodopropen-1-yl)-2 beta-carbomethoxy-3 beta (4-chlorophenyl)tropanes: potential dopamine reuptake site imaging sites," J. Med. Chem. 37:1535-1542 (1994).
Innis, R., "Single-Photon Emission Tomography Imaging of Dopamine Terminal Innervation: A Potential Clinical Tool in Parkinson's Disease," Eur. J. Nucl. Med. 21:1-5 (1994).
Innis, R.B. et al., "Single-Photon Emission-Computed Tomography Imaging Demonstrates Loss of Triatal Dopamine Transporters in Parkinson's Disease," Proc. Natl. Acad. Sci. USA 90:11965-11969 (1993).
Jurisson, S. et al., "Coordination Compounds in Nuclear Medicine," Chem. Rev. 93:1137-1156 (1993).
Jurisson, S. et al., "Boronic acid adducts of technetium dioxime (BATO) complexes derived from quinuclidine benzilate (QNB) boronic acid stereoisomers: syntheses and studies of their binding to the muscarinic acetylcholine receptor," Nucl. Med. Biol. 22:269-281 (Apr. 1995).
Kilbourn, M.R., "In vivo binding of [18F]GBR 13119 to the brain dopamine uptake system," Life Sci. 42:1347-1353 (1988).
Kolb, U. et al., "Heterocyclic Systems Containing Tin (IV) 10.sup.1 Control of Three-Center Interaction X . . . Sn-Hal in Stannocanes by Halide Type," Inorg. Chem. 33:4522-4530 (1994).
Kozikowski, A. et al., "Chemistry and Biology of the 2.alpha.-Alkyl-3.beta.-phenyl Analogues of Cocaine: Subnanomolar Affinity Ligands That Suggests a New Pharmacophore Model at the C-2 Position," J. Med. Chem. 38:3086-3093 (Aug. 1995).
Kuikka, J.T. et al., "Iodine-123 labelled N-(2-Fluoroethyl)-2.beta.-Carbomethoxy-3.beta.-(4-Iodophenyl) Nortropane for Dopamine Transporter Imaging in the Human Brain," Eur. J. Nucl. Med. 22: 682-686 (Jul. 1995).
Kung, M.-P. et al., "IPT: a Novel Iodinated Ligand for the CNS Dopamine Tranporter," Synapse 20:316-324 (Aug. 1995).
Kung, H.F. et al., "Imaging of dopamine transporters in humans with technetium-99m TRODAT-1," Eur. J. Nucl. Med. 23:1527-1530 (Nov. 1996).
Lever, S. et al., "Novel Technetium Ligands with Affinity for the Muscarinic Cholinergic Receptor," Nucl. Med. Biol. 21:157-164 (1994).
Mach, R. et al., "Synthesis and Biodistribution of a New Class of .sup.99m Tc-labeled Fatty Acid Analogs for Myocardial Imaging," Nucl. Med. Biol. 18:215-226 (1991).
Madras, B.K. et al., "Technepine: A High-Affinity .sup.99m Technetium Probe to Label the Dopamine Transporter in brain by SPECT Imaging," Synapse 22:239-246 (Mar. 1996).
Malison, R. et al., "Striatal Dopamine Transporter Imaging in Nonhuman Primates with Iodine-123-IPT SPECT," J. Nucl. Med. 36:2290-2297 (Dec. 1995).
Mastrostamatis, S. et al., "Tridentate Ligands Containing the SNS Donor Atom Set as a Novel Backbone for the Development of Technetium Brain-Imaging Agents," J. Med. Chem. 37:3212-3218 (1994).
Meegalla, S. et al., "First Example of a .sup.99m Tc Complex as a Dopamine Transporter Imaging Agent," J. Amer. Chem. Soc. 117:11037-11038 (1995).
Meegalla, S. et al. "Tc-99m-labeled tropanes as dopamine transporter imaging events," Bioconjug. Chem. 7:421-429 (Jul.-Aug. 1996).
Meegalla, S. et al., "Synthesis and Characterization of Technetium-99m-Labeled Tropanes as Dopamine Transporter-Imaging Agents," J. Medicinal Chem. 40:9-17 (Jan. 1997).
Meltzer, P.C. et al., "Substituted 3-Phenyltropane Analogs of Cocaine: Synthesis, Inhibition of Binding at Cocaine Recognition Sites, and Positron Emission Tomography Imaging," J. Med. Chem. 36:855-862 (1993).
Mozley, P.D. et al., "Dosimetry of an Iodine-123-Labeled Tropane to Image Dopamine Transporters," J. Med. Chem. 37:1558-1561 (1994).
Mozley, P.D. et al., "Dosimetry of a D2/D3 Dopamine Receptor Antagonist That Can Be Used with PET or SPECT," J. Nucl. Med. 36:1322-1331 (Jul. 1995).
Mozley, P.D. et al., "Dosimetry of an Iodine-123-Labeled Tropane to Image Dopamine Transporters," J. Nucl. Med. 37:151-159 (Jan. 1996).
Neumeyer, J. et al., "N-omega-fluoroalkyl analogs of (1R)-2 beta-carbomethoxy-3 beta-(4-iodophenyl)-tropane (beta-CIT): radiotracers for positron emission tomography and single photon emission computed tomography imaging of dopamine transporters," J. Med. Chem. 37:1558-1561 (1994).
Ohmomo, Y. et al., "New Conformationally Restricted .sup.99m Tc N.sub.S S.sub.2 Complexes as Myocardial Perfusion Imaging Agents," J. Med. Chem. 35:157-162 (1992).
O'Neil, J. e
Kung Hank
Kung Mei-Ping
Meegalla Sanath
Dees Jos,e G.
Jones Dameron
The Trustees of University of Pennsylvania
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