Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2006-09-12
2006-09-12
Aulakh, Charanjit S. (Department: 1625)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C546S124000, C546S112000
Reexamination Certificate
active
07105678
ABSTRACT:
Radiopharmaceutical compounds are disclosed. A tropane compound is linked through the N atom at the 8-position to a chelating ligand capable of complexing technetium or rhenium to produce a neutral labeled complex that selectively binds to the dopamine transporter over the serotonin transporter with a ratio of 10 or more. These compounds can be prepared as separate diastereoisomers as well as a mixture of diastereoisomers. Also disclosed are radiopharmaceutical kits for preparing the labeled radiopharmaceutical compounds.
REFERENCES:
patent: 3813404 (1974-05-01), Clarke et al.
patent: 4434151 (1984-02-01), Byrne et al.
patent: 4673562 (1987-06-01), Davison et al.
patent: 4746505 (1988-05-01), Jones et al.
patent: 5122361 (1992-06-01), Kung et al.
patent: 5128118 (1992-07-01), Carroll et al.
patent: 5310912 (1994-05-01), Neumeyer et al.
patent: 5334728 (1994-08-01), Kung et al.
patent: 5380848 (1995-01-01), Kuhar et al.
patent: 5413779 (1995-05-01), Kuhar et al.
patent: 5426189 (1995-06-01), Kung et al.
patent: 5439666 (1995-08-01), Neumeyer et al.
patent: 5493026 (1996-02-01), Elmaleh et al.
patent: 5496953 (1996-03-01), Kuhar et al.
patent: 5760055 (1998-06-01), Davies
patent: 5980860 (1999-11-01), Kung et al.
patent: 6008227 (1999-12-01), Davies et al.
patent: 6350758 (2002-02-01), Kozikowski et al.
patent: 6358492 (2002-03-01), Kuhar et al.
patent: 0 135 160 (1985-05-01), None
patent: WO 93/09814 (1993-05-01), None
patent: WO 94/26274 (1994-11-01), None
patent: WO 95/11901 (1995-05-01), None
patent: WO 97/14445 (1997-04-01), None
patent: WO 97 16210 (1997-05-01), None
patent: WO 97 47328 (1997-12-01), None
patent: WO 98/24788 (1998-11-01), None
Cesati R R III et al; “Synthesis of cyclopentadienyl tricarbonyl technetium phenyl-tropane derivatives by direct double ligand transfer with ferrocene precursors.” Journal of Labelled Compounds and Radiopharmaceuticals; vol. 42; Suppl. 1, Jun. 1999; pp. S150-S152.
Fang P et al; “Radiopharmacology study of 99mTc-TRODAT-1 as a dopamine transporters imaging agent.” Journal of Labelled Compounds and Radiopharmaceuticals; vol. 42; Suppl. 1, Jun. 1999, pp. S336-S338.
Hoepping, A. et al; “11. Improved synthesis and biological evaluation of [99mTc] technepine and comparison with a modified technepine containing a hexyl linker (hexyltecnepine)” Forschungszent. Rossendorf, 'BER.! FZR, 1997; vol. FZR-200; pp. 33-36.
Hoepping A. et al; “Novel rhenium complexes derived from alpha-tropanol as potential ligands for the dopamine transporter.” Bioorganic & Medicinal Chemistry; vol. 6; No. 10, pp. 1663-1672, 1998.
Hoepping A et al; “Retropane—a new Rhenium Complex as a potential Ligand to label the Dopamine Transporter” Bioorganic & Medicinal Chemistry Letters, vol. 6; No. 23, Dec. 3, 1996, pp. 2871-2874.
Hoepping A. et al; “TROTEC-1; A new high-affinity ligand for labeling of the dopamine transporter”; Journal of Medicinal Chemistry, Nov. 5, 1998, vol. 41; No. 23, pp. 4429-4432.
Madras et al; “Technepine: a high-affinity 99Technetium probe to label the dopamine transporter in brain by SPECT imaging” Synapse, vol. 22; No. 3; Mar. 1996, pp. 239-246.
Meegalla, Sanath K. et al; “Synthesis and Charactrerization of Technetium-99m-Labeled Tropanes as Dopamine Transporter-Imaging Agents”; J. Med. chem., 1997, vol. 40; No. 1, pp. 9-17.
Meltzer PC et al; “A technetium-99m SPECT imaging agent which targets the dopamine transporter in primate brain.” Journal of Medicinal Chemistry; Jun. 6, 1997, vol. 40; No. 12, pp. 1835-1844.
Meltzer PC et al; “Substituted 3-Phenyltropane Analogs of Cocaine: Synthesis, Inhibition of Binding at Cocaine Recognition Sites, and Positron Emission Tomography Imaging”; Journal of Medicinal Chemistry; vol. 36; 1993, pp. 855-862.
Meltzer et al; “Structure-activity-relationships of Inhibition of the Dopamine Transporter by 3-Arylbicyclo [3.2.1] octanes”; Medicinal Chemistry Research, vol. 8; No. 1/2, 1998, pp. 12-34.
S. Meegalla, et al.; “First Example of a99mTc Complex as a Dopamine Transporter Imaging Agent”; J. Am. Chem. Soc.; 1995; pp. 11037-11038.
S. Meegalla, et al.; “Tc-99m-Labeled Tropanes as Dopamine Transporter Imaging Agents”; Bioconjugate Chem.l, 1996 pp. 421-429.
Brandau, et al.,Nucl. Med. Biol.21, No. 8, pp. 1073-1081. (1994).
Bryson, et al.,Inorg. Chem.1988, 27, pp. 2154-2161.
Davison, A., et al.,Inorg. Chem.1981, vol. 20, No. 6, pp. 1629-1632.
DiZio, J. P., et al.,Bioconj. Chem.1991, 2, pp. 353-366.
DiZio, J.P., et al.,J. Nucl. Med.1992, vol. 33, No. 4, pp. 558-569.
Fritzberg et al.,J. Nucl. Med.1981, vol. 22, No. 3, pp. 258-263.
Fritzberg et al.,J. Nucl. Med.1982, vol. 23, No. 7, pp. 592-598.
Gustavson, L.M., et al.,Tet. Lett.1991, 32, pp. 5484-5488.
Hansen, et al.,J. Nucl. Med.1994, vol. 35, No. 7, pp. 1198-1205.
Jones, et al.,J. Nucl. Med.1982, vol. 23, No. 9, pp. 801-809.
Steignman, et al.,The Chemistry of Technetium in Medicine1992, pp. 117-127.
Archer, et al.,New Hydrophilic Ligands for99mTc-Based Radiopharmaceuticals, Technetium and Rhenium in Chemistry and Nuclear Medicine 4, eds. M. Nicolini, G. Bandoli, U. Mazzi, Servizi Grafici Editoriali, Padua, 1995, pp. 177-179.
Baldwin, et al.,Synthesis and Biodistribution of99mTc Aromatic Amine-Amide-Thiol-Thioether N2S2Complexes, Technetium and Rhenium in Chemistry and Nuclear Medicine 4, eds. M. Nicolini, G. Bandoli, U. Mazzi, Servizi Grafici Editoriali, Padua, 1995, pp. 329-332.
Kelly, et al.,Low Lipophilicity Technetium-99m Complexes for Radiopharmaceutical Applications, Technetium and Rhenium in Chemistry and Nuclear Medicine 4, eds. M. Nicolinin, G. Bandoli, U. Mazzi, Servizi Grafici Editoriali, Padua, 1995, pp. 259-263.
Kung, H.F., et al.,New TcO(111)and ReO(III)N2S2Complexes as Potential CNS 5-HT1AReceptor Imaging Agents, Technitium and Rhenium in Chemistry and Nuclear Medicine 4, eds. M. Nicolini, G. Bandoli, U. Mazzi, Servizi Grafici Editoriali, Padua, 1995, pp. 293-298.
Liu, et al.,New NzS2Diamidedithiol and N3S Triamidethiols as Bifunctional Chelating Agents for Labelling Small Peptides with Technetium-99m, Technetium and Rhenium in Chemistry and Nuclear Medicine 4, eds. M. Nicolini, G. Bandoli, U. Mazzi, Servizi Grafici Editoriali, Padua, 1995, pp. 383-393.
Mahmood, et al.,Technetium and Rhenium Complexes of Amine Amide Dithiol Ligands: Ligand Synthesis and Metal Complexes, Technetium and Rhenium in Chemistry and Nuclear medicine 4, eds. M. Nicolini, G. Bandoli, U. Mazzi, Servizi Grafici Editoriali, Padua, 1995, pp. 211-215.
Volkert, W.A.,Ligand System Useful in Designing High Specific Activity99mTc or186/188Re Radiopharmaceuticals, Technetium and Rhenium in Chemistry and Nuclear Medicine 4, eds. M. Nicolini, G. Bandoli, U. Mazzi, Servizi Grafici Editoriali, Padua, 1995, pp. 17-26.
Davies et al., (1994),J. Med. Chem.vol. 37, pp. 1262-1268, “Synthesis of α -acyl-3B-aryl-8-azgbicyclo [3.2.1] octanes and their binding affinities at Dopamine and Serotonin transport sites in rat striatum and frontal cortex”.
Bennett et al (Mar. 1995)The Journal of Pharmacology and Experimental Theraupeutics, vol. 272, No. 3. pp. 1176-1186. “Novel 2-substituted cocaine analogs: uptake and Ligand Binding studies at depainine, serotonin, and norepinephrine transport sites in the rat brain.”.
T.N. Rao, et al.,Monoamide Monoamine Dithiolate Ligands(MAMA)As Chelating Agents for Technetium: Kinetic And Mechanistic Studies of Complex Formation, in Eight International Symposium on Radiopharmaceutical Chemistry, 1990, pp. 39-40.
H. Spies, et al.,Technetium And Rhenium Complexes As Potential Receptor Biding Ligands, Abstract in Eleventh International Symposium on Radiopharmaceutical Chemistry, 1995, pp. 319-320.
P.D. Mozley, et al., Abstract No. 123, inThe Journal of Nuclear Medicine, IPT Spect Imaging in Healthy Volunteers: Evaluating Changesin the Dopamine Reuptake Transporter With Normal Againg, vol. 36, No. 5, May 1995, pp. 32P.
A.M. Myers, et al., Abstract N
Blundell Paul
Madras Bertha C.
Meltzer Peter C.
Aulakh Charanjit S.
Edwards Angell Palmer & & Dodge LLP
Neuner George
Organix Inc.
President and Fellows of Harvard College
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