Methods of making radiolabeled tracers and precursors thereof

Details Methods of making radiolabeled tracers and precursors thereof Methods of making radiolabeled tracers and precursors thereof

2006-07-25

2010-11-02

Hartley, Michael G (Department: 1618)

Drug, bio-affecting and body treating compositions

Radionuclide or intended radionuclide containing; adjuvant...

C424S001890

Reexamination Certificate

active

07824659

ABSTRACT:
The present disclosure relates to a solid-phase process for the production of radiolabeled tracers, in particular for the production of18F-labeled compounds which may be used as Positron Emission Tomography (PET) radiolabeled tracers. The disclosure also relates to radiopharmaceutical kits comprising precursors to the radiolabeled tracers, which can be converted to the radiolabeled tracers using the processes described herein.

REFERENCES:
patent: 3359103 (1967-12-01), Becker et al.
patent: 5087440 (1992-02-01), Cacheris et al.
patent: 5088499 (1992-02-01), Unger
patent: 5155215 (1992-10-01), Ranney
patent: 5169848 (1992-12-01), Bettarini et al.
patent: 5228446 (1993-07-01), Unger et al.
patent: 5281704 (1994-01-01), Love et al.
patent: 5412148 (1995-05-01), Keana
patent: 5417959 (1995-05-01), Wallace
patent: 5520904 (1996-05-01), Nosco et al.
patent: 5547656 (1996-08-01), Unger
patent: 5567411 (1996-10-01), Keana et al.
patent: 5585112 (1996-12-01), Unger et al.
patent: 5587491 (1996-12-01), Hoye et al.
patent: 5679810 (1997-10-01), Love et al.
patent: 5760191 (1998-06-01), Snow et al.
patent: 5801228 (1998-09-01), Hollister et al.
patent: 5804161 (1998-09-01), Long et al.
patent: 5846517 (1998-12-01), Unger
patent: 6056939 (2000-05-01), Desreux et al.
patent: 6241964 (2001-06-01), Burns et al.
patent: 6565889 (2003-05-01), Zasadzinski et al.
patent: 7112318 (2006-09-01), Madar et al.
patent: 7344702 (2008-03-01), Casebier et al.
patent: 7410998 (2008-08-01), Nicolaou et al.
patent: 7485283 (2009-02-01), Radeke et al.
patent: 2003/0044354 (2003-03-01), Carpenter et al.
patent: 2004/0033197 (2004-02-01), Madar et al.
patent: 2004/0034239 (2004-02-01), Nicolaou et al.
patent: 2008/0112884 (2008-05-01), Casebier et al.
patent: 2009/0104118 (2009-04-01), Radeke et al.
patent: 0727225 (1996-08-01), None
patent: WO-91/14460 (1991-10-01), None
patent: WO-92/17215 (1992-10-01), None
patent: WO-94/22496 (1994-10-01), None
patent: WO-02/20008 (2002-03-01), None
patent: WO 03/002157 (2003-01-01), None
patent: WO-03/082350 (2003-10-01), None
patent: WO-03/086476 (2003-10-01), None
patent: WO 2004/056400 (2004-07-01), None
patent: WO 2005/012319 (2005-02-01), None
patent: WO 2005/079391 (2005-09-01), None
patent: WO 2005/105159 (2005-11-01), None
Bousquet, J.-C. et al., “Gd-DOTA: Characterization of a New Paramagnetic Complex,” Radiology, vol. 166, No. 3, pp. 693-698 (1988).
Brown, M. et al., “Delineation of myocardial oxygen utilization with carbon -11-labeled acetate,” Circulation, vol. 76, No. 3, pp. 687-696 (1987).
Esposti, M. D., “Inhibitors of NADH—ubiquinone reductase: an overview,” Biochimica et Biophysica Acta, vol. 1364, pp. 222-235 (1998).
Gout, P. W. et al., “Sulfasalazine, a potent suppressor of lymphoma growth by inhibition of the xccystine transporter: a new action for an old drug,” Leukemia, vol. 15, pp. 1633-1640 (2001).
Han, H. et al., “Total Synthesis of 34-hydroxyasimicin and Its Photoactive Derivative for Affinity Labeling of the Mitochondrial Complex I,” Chemistry—A European Journal, vol. 10, No. 9, pp. 2149-2158 (2004).
Jiang, S. et al., “Mimicry of annonaceous acetogenins: Enantioselective syntheiss of a (4R)-hydroxy analogue having potent antitumor activity,” J. Org. Chem., vol. 67, No. 10, pp. 3404-3408 (2002).
Krivokapich, J. et al., “13N Ammonia Myocardial Imaging at Rest and With Exercise in Normal Volunteers, Quantification of Absolute Myocardial Perfusion With Dynamic Positron Emission Tomography,” Circulation, vol. 80, No. 5, pp. 1328-1337 (1989).
Lindell, S. D. et al., “The design and synthesis of novel inhibitors of NADH: ubiquinone oxidoreductase,” Bioorganic & Medicinal Chemistry Letters, vol. 14, pp. 511-514 (2004).
Liu. S. et al., “Integrin avb3 directed radiopharmaceuticals for tumor imaging,” Drugs of the Future, vol. 28, No. 6, pp. 551-564 (2003).
Magerstadt, M. et al., “Gd(DOTA): An Alternative to Gd(DTPA) as a T1,2 Relaxation Agent for NMR Imaging of Spectroscopy,” Magnetic Resonance in Medicine, vol. 3, pp. 808-812 (1986).
Marshall, R. C. et al., “Kinetic Analysis of a125I-iodorotenone as a deposited myocardial flow tracer: Comparison with99mTc-sestamibi,” Journal of Nuclear Medicine, vol. 42, No. 2, pp. 272-281 (2001).
Marshall, R. C. et al., “Kinetic Analysis of a18F-fluorodihydrorotenone as a deposited myocardial flow tracer: Comparison with291TI,” Journal of Nuclear Medicine, vol. 45, No. 11, pp. 1950-1959 (2004).
Martarello, L. et al., “Synthesis and evaluation of a new fluorine-18 labeled rotenoid as a potential pet probe of mitochondrial complex I activity,” Journal of Labelled Compounds and Radiopharmaceuticals, vol. 42, No. 11, pp. 1039-1050 (1999).
Miyoshi, H. et al., “Essential structural factors of annonaceous acetogenenins as potent inhibitors of mitochondrial complex I,” Biochimica et Biophysica Acta, vol. 1365, No. 3, pp. 443-452 (1998).
Nakanishi, Y. et al., “Acetogenins as selective inhibitors of the human ovarian 1A9 tumor cell line,” Journal of Medicinal Chemistry, vol. 46, No. 15, pp. 3185-3188 (2003).
Nicolaou, K. C. et al., “Combinatorial synthesis of novel and potent inhibitors of NADH: ubiquinone oxidoreductase,” Chemistry & Biology, vol. 7, pp. 979-992 (2000).
Pauwels, E. K. J. et al., “Fluorine-18-radiolabeled pharmaceuticals for imaging with positron emission tomography, excluding [18F]-fluorodeoxyglucose,” Drugs of the Future, vol. 27, pp. 655-667 (2002).
Runge, V. M. et al., “MR Imaging of Rat Brain Glioma: Gd-DTPA versus Gd-DOTA,” Radiology, vol. 166, No. 3, pp. 835-838 (1988).
Schuler, F. et al., “Functional coupling of PSST and ND1 subunits in NADH: ubiquinone oxidoreductase established by photoaffinity labeling,” Biochimica et Biophysica Acta, vol. 1506, pp. 79-87 (2001).
Vanbrocklin, H. F. et al., “(F-18)fluorodihydrorotenone: Synthesis and evaluation of a mitochondrial electron transport chain (ETC) complex I probe for PET,” Journal of Nuclear Medicine, vol. 35, No. 5 Suppl., p. 73P (1994).
Walker, J. E., “The NADH: ubiquinone oxidoreductase (complex I) of respiratory chains,” Quarterly Review of Biophysics, vol. 25, No. 3, pp. 253-324 (1992).
Yu, M. et al., “BMS-747158-02: a novel PET myocardial perfusion imaging agent,” Journal of Nuclear Cardiology, vol. 14. No. 6, pp. 789-798 (2007).
International Search Report and Written Opinion mailed Oct. 21, 2005 in connection with application No. PCT/US05/014459.
International Preliminary Report on Patentability mailed Nov. 1, 2006 in connection with application No. PCT/US05/014459.
International Search Report and Written Opinion mailed Nov. 17, 2005 in connection with application No. PCT/US05/004687.
International Preliminary Report on Patentability mailed Aug. 14, 2006 in connection with application No. PCT/US05/004687.
Supplementary European Search Report mailed Dec. 5, 2008 in connection with application No. EP 05723066.6.
Supplementary European Search Report mailed Jul. 17, 2009 in connection with application No. EP 05756378.5.
International Search Report and Written Opinion mailed Mar. 15, 2007 in connection with application No. PCT/US2006/031231.
International Preliminary Report on Patentability mailed Feb. 21, 2008 in connection with application No. PCT/US2006/031231.

Affiliated with

Also associated with

Rating

Methods of making radiolabeled tracers and precursors thereof does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Methods of making radiolabeled tracers and precursors thereof, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Methods of making radiolabeled tracers and precursors thereof will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-4251146