Radiolabelled benzamide analogues, their synthesis and use...

Details Radiolabelled benzamide analogues, their synthesis and use... Radiolabelled benzamide analogues, their synthesis and use...

2007-06-01

2010-02-09

Seaman, D. Margaret (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C546S087000

Reexamination Certificate

active

07659400

ABSTRACT:
Fluoroalkoxybenzamide compounds which selectively bind Sigma-2 receptors are disclosed. These compounds, when labelled with18F, can be used as radiotracers for imaging of tumors by positron emission tomography (PET). In addition, these compounds, when labelled with123I, can be used as radiotracers for imaging of tumors by single photon emission computed tomography (SPECT). Methods for synthesis of these compounds are also disclosed.

REFERENCES:
patent: 6046210 (2000-04-01), Stemp et al.
patent: 6113877 (2000-09-01), Mach et al.
patent: 6447748 (2002-09-01), John et al.
patent: 2005/0107398 (2005-05-01), Mach et al.
patent: 2008/0161343 (2008-07-01), Mach et al.
patent: WO 2005/048810 (2005-06-01), None
Huang et al. Journal of Medicinal Chemistry, 2001, 44, 1815-1826, p. 1816.
Yu et al. Journal of Medicinal Chemistry (2007), 50(14), 3194-3204.
Supplementary Partial European Search Report issued on Oct. 10, 2008, in related application 04817745.5.
Curtet et al, New arylpiperazine derivatives as antagonists of the human cloned 5-HT4 receptor isoforms, J Med Chem, 2000, 43:3761-3769.
Hackling et al, N-(omega-(4-(2-methoxyphenyl)piperazin-1-yl)alkyl)carboxamides as dopamine D2 and D3 receptor ligands, J Med Chem, 2003, 46:3883-3899.
Leopoldo et al, Structure-affinity relationship study on N-[4-(4-arylpiperazin-1-yl)butyl]aryl carboxamides as potent and selective dopamine D3 receptor ligands, J Med Chem, 2002, 45:5727-5735.
International Search Report in the related application PCT/US08/655555 issued on Mar. 3, 2009.
International Preliminary Report on Patentability, Feb. 6, 2006.
Al-Nabulsi I, et al., Effect of ploidy, recruitment, environmental factors, and tamoxifen treatment on the expression of sigma-2 receptors in proliferating and quiescent tumour cells, Br. J. Cancer, 1999, p. 925-933, vol. 81(6).
Anderson CJ and Welch MJ, Radiometal-labeled agents (non-technetium) for diagnostic imaging, Chem. Rev., 1999, p. 2219-2234, vol. 99(9).
Berardi F, et al., 4-(tetralin-1-yl)- and 4-(naphthalen-1-yl)alkyl derivatives of 1-cyclohexylpiperazine as sigma receptor ligands with agonist sigma2 activity, J. Med. Chem., 2004, p. 2308-2317, vol. 47(9).
Bonhaus DW, et al., [3H]BIMU-1, a 5-hydroxytryptamine3 receptor ligand in NG-108 cells, selectively labels sigma-2 binding sites in guinea pig hippocampus, J. Pharmacol. Exp. Ther., 1993, p. 961-970, vol. 267(2).
Bowen WD, et al., Ibogaine and its congeners are sigma 2 receptor-selective ligands with moderate affinity, Eur. J. Pharmacol., 1995, p. 257-260, vol. 278(3).
Colabufo NA, et al., Distribution of sigma receptors in EMT-6 cells: preliminary biological evaluation of PB167 and potential for in-vivo PET, J. Pharm. Pharmacol., 2005, p. 1453-1459, vol. 57(11).
Hou C, et al., Characterization of a novel iodinated sigma-2 receptor ligand as a cell proliferation marker, Nucl. Med. Biol., 2006, p. 203-209, vol. 33(2).
Huang Y, et al., Synthesis and structure-activity relationships of naphthamides as dopamine D3 receptor ligands, J. Med. Chem., 2001, p. 1815-1826, vol. 44(11).
Jurisson SS and Lydon JD, Potential technetium small molecule radiopharmaceuticals, Chem. Rev., 1999, p. 2205-2218, vol. 99(9).
Kassiou M, et al., Synthesis and in vivo evaluation of a new PET radioligand for studying sigma-2 receptors, Bioorg. Med. Chem., 2005, p. 3623-3626, vol. 13(11).
Laforest R, et al., MicroPET imaging with nonconventional isotopes, IEEE Transactions on Nuclear Science, 2002, p. 2119-2126, vol. 49(5).
Mach RH, et al., Sigma 2 receptors as potential biomarkers of proliferation in breast cancer, Cancer Res., 1997, p. 156-161, vol. 57(1).
Mach RH, et al., [[ (18)F]N-(4′-fluorobenzyl)-4-(3-bromophenyl) acetamide for imaging the sigma receptor status of tumors: comparison with [(18)F]FDG, and [(125)l]IUDR, Nucl. Med. Biol., 2001, p. 451-458, vol. 2B(4).
Mach RH, et al., Synthesis of 2-(5-bromo-2,3-dimethoxyphenyl)-5-(aminomethyl)-1H-pyrrole analogues and their binding affinities for dopamine D2, D3, and D4 receptors, Bioorg. Med. Chem., 2003, pp. 225-233, vol. 11 (2).
Mach RH, et al., Conformationally-flexible benzamide analogues as dopamine D3 and sigma 2 receptor ligands, Bioorg. Med. Chem. Lett., 2004, p. 195-202, vol. 14(1).
Tu Z, et al., Carbon-11 labeled sigma2 receptor ligands for imaging breast cancer, Nucl. Med. Biol., 2005, p. 423-430, vol. 32(5).
Wheeler KT, et al., Sigma-2 receptors as a biomarker of proliferation in solid tumours, Br. J. Cancer, 2000, p. 1223-1232, vol. 82(6).
Xu J, et al., [3H]N-[4-(3,4-dihydro-6,7-dimethoxyisoquinolin-2(1H)-yl)butyl]-2-methoxy-5-methylbenzamide: a novel sigma-2 receptor probe, Eur. J. Pharmacol., 2005, p. 8-17, vol. 525(1-3).

Affiliated with

Also associated with

Rating

Radiolabelled benzamide analogues, their synthesis and use... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Radiolabelled benzamide analogues, their synthesis and use..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Radiolabelled benzamide analogues, their synthesis and use... will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-4209135