Fluorinated phenyl thiophenyl derivatives and their use for...

Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing

Reexamination Certificate

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C514S612000, C514S649000, C514S653000

Reexamination Certificate

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07041851

ABSTRACT:
This invention relates to novel fluorinated phenyl thiphenyl (also named diarylsulfide) derivatives and their use in Positron Emission Tomagraphy (PET) imaging of Serotonin Transporters (SERTS). The present invention also provides diagnostic compositions comprising the novel compounds of the present invention, and a pharmaceutically acceptable carrier or diluent. The invention further provides a method of imaging SERTS, comprising introducing into a patient a detectable quantity of a labeled compound of the present invetion, or a pharmaceutically acceptable salt, ester, amide or prodrug thereof.

REFERENCES:
patent: 0 402 097 (1990-12-01), None
patent: 0 282 944 (1996-11-01), None
patent: 1 207 725 (1970-10-01), None
patent: WO 93/12080 (1993-06-01), None
patent: WO 97/17325 (1997-05-01), None
patent: WO 03/096978 (2003-11-01), None
Acton, P.D., et al., “Single-photon emission tomography imaging of serotonin transporters in the non-human primate brain with the selective radioligand [123I] IDAM,”Eur. J. Nucl. Med.26:854-861, Springer-Verlag (1999).
Acton, P.D., et al., “Single-photon emission tomography imaging of serotonin transporters in the non-human primate brain with [123I]ODAM,”Eur. J. Nucl. Med.26:1359-1362, Springer-Verlag (1999).
Acton, P.D., et al., “Quantification of Serotonin Transporters in Nonhuman Primates Using [123I]ADAM and SPECT,”J. Nucl. Med.42:1556-1562, Society of Nuclear Medicine (Oct. 2001).
Angelini, G., et al., “New developments in the synthesis of no-carrier-added (NCA)18F-labeled aryl fluorides using the nucleophilic aromatic substitution reaction,”J. Labelled Cpd. Radiopharm.21:1223-1225, John Wiley & Sons, Ltd. (1984).
Angelini, G., et al., “Nucleophilic aromatic substitution of activated cationic groups by18F-labeled fluoride. A useful route to no-carrier-added (NCA)18F-labeled aryl fluorides,”J. Fluor. Chem.27:177-191, Elsevier Sequoia (1985).
Attiná, “Displacement of a Nitro-group by [18F]Fluoride Ion. A New Route to Aryl fluorides of High Specific Activity,”J. Chem. Soc. Chem. Commun.No. 3, 108-109, Royal Society of Chemistry, London (1983).
Attinà, M., et al., “Labeled aryl fluorides from the nucleophilic displacement of activated nitro groups by18F-F-, ”J. Labelled Cpd. Radiopharm.20:501-514, John Wiley & Sons, Ltd., (1983).
Bergström, K.A., et al., “In vitro and in vivo characterisation of nor-β-CIT: a potential radioligand for visualisation of the serotonin transporter in the brain,”Eur. J. Nucl. Med.24:596-601, Springer-Verlag (1997).
Berridge, M.S., et al., “Aromatic fluorination with N.C.A. F-18 fluoride: A comparative study,”J. Labelled Cpd. Radiopharm.22:687-694, John Wiley & Sons, Ltd. (1985).
Biegon, A., et al., [125I]5-Iodo-6-nitroquipazine: a potent and selective ligand for the 5-hydroxytryptamine uptake complex. II. In vivo studies in rats,Brain Res.619:236-246, Elsevier Science Publishers B.V. (1993).
Blough, B.E., et al., “3β-(4-Ethyl-3-iodophenyl)nortropane-2β-carboxylic Acid Methyl Ester as a High-Affinity Selective Ligand for the Serotonin Transporter,”J. Med. Chem.40:3861-3864, American Chemical Society (1997).
Buck, A., et al., Evaluation of Serotonergic Transporters Using PET and [11C] (+)McN-5652: Assessment of Methods,J. Cereb. Blood Flow Metab.20:253-262, Lippincott Williams & Wilkens (2000).
Choi, S-R., et al., “Selective In Vitro and In Vivo Binding of [125I]ADAM to Serotonin Transporters in Rat Brain,”Synapse38:403-412, Wiley-Liss, Inc. (2000).
Choi, S-R., et al., “Structure-activity relationship of analogs of ADAM as ligands for serotonin transporters,”J. Labelled Cpd. Radiopharm. 44(Suppl. 1):S190-S192, John Wiley & Sons, Ltd. (May 2001).
Chumpradit, S., et al., “Iodinated Tomoxetine Derivatives as Selective Ligands for Serotonin and Norepinephrine Uptake Sites,”J. Med. Chem.35:4492-4497, American Chemical Society (1992).
Constantinou, M., et al., “Radiofluoridations ofm-substituted nitrobenzenes,”J. Labelled Cpd. Radiopharm. 44(Suppl. 1):S889-S891, John Wiley & Sons, Ltd. (May 2001).
Coryell, W., “The Treatment of Psychotic Depression,”J. Clin. Psychiatry 59(Suppl. 1):22-27, Physicians Postgraduate Press (1998).
D'Amato, R.J., et al., “Selective Labeling of Serotonin Uptake Sites in Rat Brain by [3H]Citalopram Contrasted to Labeling of Multiple Sites by [3H]Imipramine,”Pharmacol. Exp. Ther.242:364-371, The Williams & Wilkins Company (1987).
Das, M.K., and Mukherjee, J., “Radiosynthesis of [F-18]Fluoxetine as a Potential Radiotracer for Serotonin Reuptake Sites,”Appl. Radiat. Isot.44:835-842, Pergamon Press, Ltd. (1993).
Douglass, I.B., and Farah, B.S., “The Anhydrous Chlorination of Some Mercapto Acids and Analogous Disulfides1.2.3,”J. Org. Chem.26:351-354, American Chemical Society (1961).
Drouin, J., et al., “Reduction of Nitrobenzene with Sodium Borohydride-Copper(II) Sulfate System: A Reinvestigation,”SYNLETT9:791-793, Thieme (1993).
Elfving, B., et al., “Binding Characteristics of Selective Serotonin Reuptake Inhibitors With Relation to Emission Tomography Studies,”Synapse41:203-211, Wiley-Liss, Inc. (Sep. 2001).
Emond, P., et al., “Substituted Diphenyl Sulfides as Selective Serotonin Transporter Ligands: Synthesis and In Vitro Evaluation,”J. Med. Chem.45:1253-1258, American Chemical Society (Published on Web Feb. 9, 2002).
Ferris, R.M. et al., “Pharmacological Properties of 403U76, a New Chemical Class of 5-Hydroxytryptamine- andNoradrenaline- reuptake Inhibitor,”J. Pharm. Pharmacol.47:775-781, Pharmaceutical Press (1995).
Frazer, A., and Hensler, J.G., “5-HT1AReceptors and 5-HT2A-Mediated Responses: Effect of Treatments That Modify Serotonergic Neurotransmission,”Ann. NY Acad. Sci. 600:460-475, New York Academy of Sciences (1990).
Frazer, A., “Antidepressants,”J. Clin. Psychiatry 58(Suppl. 6):9-25, Physicians Postgraduate Press (1997).
Frazer, A., “Serotonergic and Noradrenergic Reuptake Inhibitors: Prediction of Clinical Effects From In Vitro Potencies,”J. Clin. Psychiatry 62(Suppl. 12):16-23, Physicians Postgraduate Press (Jun. 2001).
Fujita, M., et al., “Differential kinetics of [123I]β-CIT binding to dopamine and serotonin transporters,”Eur. J. Nucl. Med.23:431-436, Springer-Verlag (1996).
Fuller, R.W., “Serotonin uptake inhibitors: Uses in clinical therapy and in laboratory research,”Prog. Drug Res.45:167-204, Birkhäuser Verlag (1994).
Ginovart, N., et al., “Positron Emission Tomography Quantification of [11C]-DASB Binding to the Human Serotonin Transporter: Modeling Strategies,”J. Cereb. Blood Flow Metab.21:1342-1353, Lippincott Williams & Wilkins, Inc. (Nov. 2001).
Gozlan, H., and Hamon, M., “Pharmacology and molecular biology of central 5-HT receptors,” inAnxiety: Neurobiology, Clinic and Therapeutic Perspectives232:141-150, INSERM/John Libbey Eurotext, Ltd. (1993).
Habert, E., et al., “Characteristization of [3H]paroxetine binding to rat cortical membranes,”Eur. J. Pharmacol.118:107-114, Elsevier (1985).
Halldin, C., et al., “11CMADAM—a selective radioligand for PET-examination of the serotonin transporter in the monkey brain,”J. Nucl. Med. 42(Suppl.):112P, Abstract No. 419, Society of Nuclear Medicine (Jun. 2001).
Halldin, C., “A PET-comparison in monkey brain of11C-MADAM labeled in two different positions—selective for the serotonin transporter,”J. Nucl. Med. 43(Suppl.):164P, Abstract No. 596, Society of Nuclear Medicine (Jun. 2002).
Hammadi, A., and Crouzel, C., “Synthesis of18F-labeled fluoxetine: A selective serotonin uptake inhibitor,”J. Labelled Cpd. Radiopharm.32:305-306, Wiley-Liss (1993).
Harvey, B.H., “The neurobiology and pharmaco

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