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(12) United States Patent (10) Patent No.: US 6,399,042 B1 G00dman Et Al USOO6399042B1 (12) United States Patent (10) Patent No.: US 6,399,042 B1 G00dman et al. (45) Date of Patent: Jun. 4, 2002 (54) 4-FLUOROALKYL-3-HALOPHENYL Hume, et al. “Citalopram: Labelling with Carbon-11 and NORTROPANES Evaluation in Rat as a Potential Radioligand for In Vivo PET Studies of 5-HT Re-uptake Sites” (1991) Nucl. Med. Biol. (75) Inventors: Mark M. Goodman, Atlanta, GA (US); 18:339-351. Ping Chen, Indianapolis, IN (US) Kilbourn et al. “Synthesis of Radiolabeled Inhibitors of Presynaptic Monoamine Uptake Systems: "FIGBR (73) Assignee: Emory University, Atlanta, GA (US) 13119(DA). 'CNisoxetine (NE), and ''CFluoxtine (5-HT)” (1989).J. Label. Cmpd. Radiopharm. 26:412–414. (*) Notice: Subject to any disclaimer, the term of this (Symposium Abstract). patent is extended or adjusted under 35 Maryanoff et al. “Pyrroloisoquinoline Antidepressants. U.S.C. 154(b) by 0 days. In-Depth Exploration of Structure-Activity Relationships” (21) Appl. No.: 09/558,916 (1987) J. Med. Chem. 30:1433–1454. Mathis et al. “Synthesis and Biological Evaluation of a PET (22) Filed: Apr. 26, 2000 Radioligand for Serotonin Uptake Sites: F-18 5-Fluoro-6-Nitroquipazine” (1993) J. Nucl. Med. Related U.S. Application Data 34:7P-8 P. (60) Provisional application No. 60/131,104, filed on Apr. 26, 1999. Murphy, D.L. et al. “Use of Serotonergic Agents in the Clinical Assessment of Central Serotonin Function” (1986) (51) Int. Cl." ....................... A61K 51/00; CO7D 451/02 J. Clin. Psychiatr. 47(Supp)9–15. (52) U.S. Cl. ..................... 424/1.85; 424/1.89; 54.6/124; Suehiro et al. “Radiosynthesis and Evaluation of N-(3–F 546/132 Fluoropropyl) paroxetine as a Radiotracer for In Vivo Label (58) Field of Search ............................... 424/1.85, 1.89; ing of Serotonin Uptake Sites by PET" (1991) Nucl. Med. 546/124, 132 Biol. 18:791-796. Suehiro et al. “Synthesis of a Radiotracer for Studying (56) References Cited Serotonin Uptake Sites with Positron Emission Tomogra U.S. PATENT DOCUMENTS phy: 'CMcN-5652–Z” (1992) J. Label Cmpd. Radiop harm. 31:841-848. 5,310,912 A * 5/1994 Neumeyer et al. ......... 424/1.85 5,413,779 A 5/1995 Kuhar et al. ............... 424/1.85 Suehiro et al. “A PET Radiotracer for Studying Serotonin Uptake Sites: Carbon-11-McN-5652Z” (1993) J. Nucl. FOREIGN PATENT DOCUMENTS Med. 34:120-127. WO 97/43285 11/1997 ......... CO7D/451/02 * cited by examiner OTHER PUBLICATIONS Blough et al. “Synthesis and Transporter Binding Properties Primary Examiner Michael G. Hartley of 3.3-(4-Alkyl-, 4-alkeny;-, and (74) Attorney, Agent, or Firm-Greenlee, Winner and 4'alkynylphenyl)nortropane-2(3-carboxylic Acid Methyl Sullivan, P.C. Esters: Serotonin Transporter Selective Analogs” (1996) J. (57) ABSTRACT Med. Chem. 39(20):4027–4035. Blough, B.E. et al. A Series of compounds in the 4-fluoroalkyl-3-halophenyl “33-(4-Ethyl-3-iodophenyl)nortropane-2B-carboxylic nortropanes family are described as diagnostic and thera Acid Methyl Ester as a High-Affinity Selective Ligand for peutic agents for diseases associated with Serotonin trans the Serotonin Transporter” (1997) J. Med. Chem. porter dysfunction. These compounds bind to Serotonin 40(24):3861–3864. transporter protein with high affinity and selectivity. The Goodman.M.M. Clinical Positron Emission Tomography invention provides methods of Synthesis which incorporate Mosby Yearbook, 1992, K.F. Hubner et al., Chapter 14 radioisotopic halogens at a last Step which permit high “Automated Synthesis of Radiotracers for PET Applica radiochemical yield and maximum uSable product life. The tions'. radiolabeled compounds of the invention are useful as Hubner, K.F. Clinical Positron Emission Tomography imaging agents for visualizing the location and density of Mosby Year Book, 1992, K.F. Hubner, et al., Chapter 2 serotonin transporter by PET and SPECT imaging. “University of Tennessee Biomedical Imaging Center and Transfer of Technology to the Clinical Floor”. 23 Claims, 6 Drawing Sheets U.S. Patent Jun. 4, 2002 Sheet 1 of 6 US 6,399,042 B1 U.S. Patent Jun. 4, 2002 Sheet 2 of 6 US 6,399,042 B1 U.S. Patent Jun. 4, 2002 Sheet 3 of 6 US 6,399,042 B1 O 60 120 180 Time (min) FIG. 3 U.S. Patent Jun. 4, 2002 Sheet 4 of 6 US 6,399,042 B1 U.S. Patent Jun. 4, 2002 Sheet 5 of 6 US 6,399,042 B1 U.S. Patent Jun. 4, 2002 Sheet 6 of 6 US 6,399,042 B1 O O 0 < é O O a 9 w O O ag O O Oak e O 3 C) O K CE O O a ce. O a gee O O a C ) O O O - Ed O O O - ge O O - d - rS O a CE O O O - Ced 6 N O O < 1 o X 2 (D O O Of Ox - O O- cs - r L O O < O-1 E 0 O a dx. O at a E 40 N O O CO - CX 0 O O 3 O1 gee O O < O € 0 CX O € 0. s i O ( et d am CO Obeg 0 O < O O X 4 O< O bo 9 O. Oled 8 : r s e (000 X Tu/CII%) US 6,399,042 B1 1 2 4-FLUOROALKYL-3-HALOPHENYL SPECT imaging employs isotope tracers that emit high NORTROPANES energy photons (y-emitters). The range of useful isotopes is greater than for PET, but SPECT provides lower three CROSS REFERENCE TO RELATED dimensional resolution. Nevertheless, SPECT is widely used APPLICATIONS to obtain clinically significant information about analog binding, localization and clearance rates. A useful isotope This application claims priority from U.S. Provisional for SPECT imaging is 'I), a Y-emitter with a 13.3 hour Application No. 60/131,104, filed Apr. 26, 1999. half life. Compounds labeled with 'I can be shipped up to about 1000 miles from the manufacturing site, or the ACKNOWLEDGEMENT OF FEDERAL isotope itself can be transported for on-site Synthesis. RESEARCHSUPPORT Eighty-five percent of the isotope's emissions are 159 KeV This invention was made, at least in part, with funding photons, which is readily measured by SPECT instrumen from the United States Department of Energy under contract tation currently in use. #DE-FG02-97ER-62367. Accordingly, the U.S. government Use of "Flabeled compounds in PET has been limited may have certain rights in this invention. 15 to a few analog compounds. Most notably, F fluorodeoxyglucose has been widely used in Studies of BACKGROUND OF THE INVENTION glucose metabolism and localization of glucose uptake asso The invention includes novel chemical compounds hav ciated with brain activity. 'F-L-fluorodopa and other ing Specific binding in a biological System and capable of dopamine receptor analogs have also been used in mapping being used for positron emission tomography (PET) and dopamine receptor distribution. Single photon emission (SPECT) imaging methods. Other halogen isotopes can serve for PET or SPECT The ability of analog compounds to bind to localized imaging, or for conventional tracer labeling. These include ligands within the body makes it possible to utilize Such 7Br, Br, 77Br and Br which have usable half-lives and compounds for in Situ imaging of the ligands by PET, emission characteristics. In general, the chemical means SPECT and Similar imaging methods. In principle, nothing 25 exist to Substitute any halogen moiety for the described need be known about the nature of the ligand, as long as isotopes. Therefore, the biochemical or physiological activi binding occurs, and Such binding is specific for a class of ties of any halogenated homolog of the described com cells, organs, tissueS or receptors of interest. PET imaging is pounds are now available for use by those skilled in the art, accomplished with the aid of tracer compounds labeled with including Stable isotope halogen homologs. AStatine can be a positron-emitting isotope (Goodman, M. M. Clinical substituted for other halogen isotopes; 'At emits alpha Positron Emission Tomography, Mosby Yearbook, 1992, K. particles with a half-life of 8.3 h. At-substituted compounds F. Hubner et al., Chapter 14). For most biological materials, are therefore useful for tumor therapy, where binding is Suitable isotopes are few. The carbon isotope, 'C), has been Sufficiently tumor-specific. used for PET, but its short half-life of 20.5 minutes limits its Serotonin transporters (SERTs) are proteins that reside on usefulness to compounds that can be Synthesized and puri 35 the membrane of the nerve terminals of the Serotoninergic fied quickly, and to facilities that are proximate to a cyclo neurons. The SERT serves to remove serotonin from the tron where the precursor'C) starting material is generated. Synapse, a process which helps regulate central nervous Other isotopes have even shorter half-lives. 'N) has a system (CNS) serotonin neurotransmission. The serotonin half-life of 10 minutes and "O) has an even shorter half-life transporter has been convincingly implicated in the patho of 2 minutes. The emissions of both are more energetic than 40 physiology of major depression and represents the putative those of 'C). Nevertheless, PET studies have been carried Sites of action of the majority of the older and newer out with these isotopes (Hubner, K. F., in Clinical Positron generation antidepressants Murphy, D. L. et al. (1986) J. Emission Tomography, Mosby Year Book, 1992, K. F. Clin. Psychiatr. 47:(suppl)9–15). Abnormalities in SERT Hubner, et al., Chapter 2). A more useful isotope,'F), has density in the midbrain and frontal corteX has also been a half-life of 110 minutes. This allows Sufficient time for 45 asSociated with obsessive compulsive disorder.
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