Title:
PRODUCTION METHOD FOR RADIOLABELED ARYL COMPOUND
Document Type and Number:
WIPO Patent Application WO/2019/027059
Kind Code:
A1
Abstract:
The purpose of the present invention is to produce a radiolabeled aryl compound by a simple method in which labeling can be carried out in a short time in high radiochemical yield and which renders the radiolabeled aryl compound usable in formulation immediately after the labeling. The present invention relates to a production method for a radiolabeled aryl compound (I), characterized by reacting an arylboronic acid compound (II) with a radioactive nuclide selected from among 211At, 210At, 123I, 124I, 125I, and 131I in water in the presence of an oxidant selected from among alkali metal iodides, alkali metal bromides, N-bromosuccinimide, N-chlorosuccinimide, and hydrogen peroxide. (In the formulae, the symbols are as defined in the description.)
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Inventors:
SHIRAKAMI YOSHIFUMI (JP)
IKEDA HAYATO (JP)
KANAI YASUKAZU (JP)
SHIMOSEGAWA EKU (JP)
HATAZAWA JUN (JP)
WATABE TADASHI (JP)
KANEDA KAZUKO (JP)
IKEDA HAYATO (JP)
KANAI YASUKAZU (JP)
SHIMOSEGAWA EKU (JP)
HATAZAWA JUN (JP)
WATABE TADASHI (JP)
KANEDA KAZUKO (JP)
Application Number:
PCT/JP2018/030006
Publication Date:
February 07, 2019
Filing Date:
August 03, 2018
Export Citation:
Assignee:
UNIV OSAKA (JP)
International Classes:
C07F13/00; C07B59/00
Domestic Patent References:
WO2007079953A2 | 2007-07-19 |
Foreign References:
JP2009521469A | 2009-06-04 | |||
US4826672A | 1989-05-02 | |||
US5077035A | 1991-12-31 | |||
JP2001503412A | 2001-03-13 | |||
JP2009521469A | 2009-06-04 | |||
JP2017151632A | 2017-08-31 |
Other References:
KABALKA, G. W. ET AL.: " "Synthesis of iodine-125 labeled 3- quinuclidinyl 4'-iodobenzilate", NTERNATIONAL JOURNAL OF RADIATION APPLICATIONS ANDINSTRUMENTATION PART B: NUCLEAR MEDICINE AND BIOLOGY, vol. 16, no. 4, 1 January 1989 (1989-01-01), pages 359 - 360, XP023085484, ISSN: 0883-2897, DOI: 10.1016/0883-2897(89)90099-8
J'VLEYER, G. J. ET AL: "Synthesis and analysis of 2-[211At]-L- phenylalanine and 4-[211At]-L-phenylalanine and their uptake in human glioma cell cultures in-vitro", APPLIED RADIATION AND ISOTOPES, vol. 68, no. 6, 1 June 2010 (2010-06-01), pages 1060 - 1065, XP026947034, ISSN: 0969-8043, DOI: 10.1016/j.apradiso.2009.12.043
WILSON, T. C. ET AL.: "Radiosynthesis of SPECT tracers via a 1-12 copper mediated123I iodination of (hetero) ary l boron reagents", CHEMICAL COMMUNICATIONS, vol. 52, no. 90, 1 January 2016 (2016-01-01), pages 13277 - 13280, XP055628019, ISSN: 1359-7345, DOI: 10.1039/C6CC07417K
KABALKA, G. W. ET AL: "No-carrier-added radiohalogenations utilizing organoboranes: The synthesis of iodine-123 labeled curcumin", JOURNAL OF ORGANOMETALLIC CHEMISTRY, vol. 694, no. 11, 1 May 2009 (2009-05-01), pages 1638 - 1641, XP026063026, ISSN: 0022-328x, DOI: 10.1016/j.jorganchem.2008.11.040
ZHANG, P. ET AL.: "A Highly Efficient Copper-Mediated Radioiodination Approach Using Aryl Boronic Acids", CHEMISTRY-A EUROPEAN JOURNAL, vol. 22, no. 47, 14 November 2016 (2016-11-14), pages 16783 - 16786, XP055627922, ISSN: 0947-6539, DOI: 10.1002/chem.201604105
AKULA, M. R. ET AL.: "No-carrier-added radioiodination of triolborates, water-soluble complexes of boronic acids", JOURNAL OF LABELLED COMPOUNDS AND RADIOPHARMACEUTICALS, vol. 54, no. 3, 1 January 2010 (2010-01-01), pages 132 - 134, XP055673878, ISSN: 0362-4803, DOI: 10.1002/jlcr.1831
"Frontiers in Neutron Capture Therapy", 2001, SPRINGER, Boston, MA, USA, ISBN: 978-1-4613-5478-9, article VAHATALO, J. ET AL.,: "Radioiodination techniques for aromatic amino acids", pages: 835 - 838, XP009519250
NUKLEARMEDIZIN, vol. 52, 2013, pages 212 - 21
APPLIED RADIATION AND ISOTOPES, vol. 68, 2010, pages 1060 - 1065
CHEM. COMMUN., vol. 52, 2016, pages 13277 - 13280
J'VLEYER, G. J. ET AL: "Synthesis and analysis of 2-[211At]-L- phenylalanine and 4-[211At]-L-phenylalanine and their uptake in human glioma cell cultures in-vitro", APPLIED RADIATION AND ISOTOPES, vol. 68, no. 6, 1 June 2010 (2010-06-01), pages 1060 - 1065, XP026947034, ISSN: 0969-8043, DOI: 10.1016/j.apradiso.2009.12.043
WILSON, T. C. ET AL.: "Radiosynthesis of SPECT tracers via a 1-12 copper mediated123I iodination of (hetero) ary l boron reagents", CHEMICAL COMMUNICATIONS, vol. 52, no. 90, 1 January 2016 (2016-01-01), pages 13277 - 13280, XP055628019, ISSN: 1359-7345, DOI: 10.1039/C6CC07417K
KABALKA, G. W. ET AL: "No-carrier-added radiohalogenations utilizing organoboranes: The synthesis of iodine-123 labeled curcumin", JOURNAL OF ORGANOMETALLIC CHEMISTRY, vol. 694, no. 11, 1 May 2009 (2009-05-01), pages 1638 - 1641, XP026063026, ISSN: 0022-328x, DOI: 10.1016/j.jorganchem.2008.11.040
ZHANG, P. ET AL.: "A Highly Efficient Copper-Mediated Radioiodination Approach Using Aryl Boronic Acids", CHEMISTRY-A EUROPEAN JOURNAL, vol. 22, no. 47, 14 November 2016 (2016-11-14), pages 16783 - 16786, XP055627922, ISSN: 0947-6539, DOI: 10.1002/chem.201604105
AKULA, M. R. ET AL.: "No-carrier-added radioiodination of triolborates, water-soluble complexes of boronic acids", JOURNAL OF LABELLED COMPOUNDS AND RADIOPHARMACEUTICALS, vol. 54, no. 3, 1 January 2010 (2010-01-01), pages 132 - 134, XP055673878, ISSN: 0362-4803, DOI: 10.1002/jlcr.1831
"Frontiers in Neutron Capture Therapy", 2001, SPRINGER, Boston, MA, USA, ISBN: 978-1-4613-5478-9, article VAHATALO, J. ET AL.,: "Radioiodination techniques for aromatic amino acids", pages: 835 - 838, XP009519250
NUKLEARMEDIZIN, vol. 52, 2013, pages 212 - 21
APPLIED RADIATION AND ISOTOPES, vol. 68, 2010, pages 1060 - 1065
CHEM. COMMUN., vol. 52, 2016, pages 13277 - 13280
Attorney, Agent or Firm:
TAKASHIMA, Hajime et al. (JP)
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