Title:
METHOD FOR PRODUCING RADIOACTIVE METAL COMPLEX
Document Type and Number:
WIPO Patent Application WO/2023/210510
Kind Code:
A1
Abstract:
Provided is a method for producing a radioactive metal complex comprising a complex forming step for causing a radioactive metal nuclide and a ligand compound represented by formula (1) to react with each other in a reaction solution containing water and a buffering agent to form a radioactive metal complex, wherein the buffering agent contains one or more types of water soluble organic compound having a sulfo group or a carboxyl group, and wherein the reaction solution is irradiated with microwave in the complex forming step while cooling the reaction solution. The radioactive metal nuclide is preferably 68Ga, 89Zr, 90Y, 111In, 177Lu, or 225Ac.
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Inventors:
ICHIKAWA HIROAKI (JP)
KISHIMOTO SATOSHI (JP)
OTSUKA YUTA (JP)
IMAI TOMOYUKI (JP)
TAKAYA HIKARU (JP)
KISHIMOTO SATOSHI (JP)
OTSUKA YUTA (JP)
IMAI TOMOYUKI (JP)
TAKAYA HIKARU (JP)
Application Number:
PCT/JP2023/015836
Publication Date:
November 02, 2023
Filing Date:
April 20, 2023
Export Citation:
Assignee:
NIHON MEDIPHYSICS CO LTD (JP)
UNIV KYOTO (JP)
UNIV KYOTO (JP)
International Classes:
C07D257/02; C07D403/12; C07F7/00
Foreign References:
| JP2008531988A | 2008-08-14 | |||
| US20150157742A1 | 2015-06-11 |
Other References:
YUSUKE YAGI, YOICHI SHIMIZU, KENJI ARIMITSU, YUJI NAKAMOTO, TAKAHIRO HIGUCHI, KAORI TOGASHI, HIROYUKI KIMURA: "Efficient gallium-68 radiolabeling reaction of DOTA derivatives using a resonant-type microwave reactor", JOURNAL OF LABELLED COMPOUNDS AND RADIOPHARMACEUTICALS, JOHN WILEY & SONS LTD., GB, vol. 62, no. 3, 1 March 2019 (2019-03-01), GB , pages 132 - 138, XP055770644, ISSN: 0362-4803, DOI: 10.1002/jlcr.3704
KUO HSIOU-TING, PAN JINHE, ZHANG ZHENGXING, LAU JOSEPH, MERKENS HELEN, ZHANG CHENGCHENG, COLPO NADINE, LIN KUO-SHYAN, BÉNARD FRANÇ: "Effects of Linker Modification on Tumor-to-Kidney Contrast of 68 Ga-Labeled PSMA-Targeted Imaging Probes", MOLECULAR PHARMACEUTICS, AMERICAN CHEMICAL SOCIETY, US, vol. 15, no. 8, 6 August 2018 (2018-08-06), US , pages 3502 - 3511, XP093103875, ISSN: 1543-8384, DOI: 10.1021/acs.molpharmaceut.8b00499
SANO KOHEI, OKADA MAYUMI, HISADA HAYATO, SHIMOKAWA KENTA, SAJI HIDEO, MAEDA MINORU, MUKAI TAKAHIRO: "In Vivo Evaluation of a Radiogallium-Labeled Bifunctional Radiopharmaceutical, Ga-DOTA-MN2, for Hypoxic Tumor Imaging", BIOLOGICAL & PHARMACEUTICAL BULLETIN, PHARMACEUTICAL SOCIETY OF JAPAN, TOKYO., JP, vol. 36, no. 4, 1 January 2013 (2013-01-01), JP , pages 602 - 608, XP093103880, ISSN: 0918-6158, DOI: 10.1248/bpb.b12-00982
YANG ZHI, XIONG CHIYI, ZHANG RUI, ZHU HUA, LI CHUN: "Synthesis and evaluation of 68 Ga-labeled DOTA-2-deoxy-D-glucosamine as a potential radiotracer in µPET imaging", AMERICAN JOURNAL OF NUCLEAR MEDICINE AND MOLECULAR IMAGING, E-CENTURY PUBLISHING CORPORATION, US, vol. 2, no. 4, 30 October 2012 (2012-10-30), US , pages 499 - 507, XP093103882, ISSN: 2160-8407
YANG ZHI, ZHU HUA: "Synthesis and Evaluation of New Nuclides Ga-68 Labeled D-Glucose for Potential PET Imaging Agent", ACTA CHIMICA SINICA, ZHONGGUO KEXUEYUAN SHANGHAI YOUJI HUAXUE YANJIUSUO, CN, vol. 70, no. 9, 1 July 2012 (2012-07-01), CN , pages 1066 - 1072, XP093103888, ISSN: 0567-7351
BLOM ELISABETH, VELIKYAN IRINA, ESTRADA SERGIO, HALL HÅKAN, MUHAMMAD TAJ, DING CHENMIN, NAIR MANOJ, LÅNGSTRÖM BENGT: "68Ga-Labeling of RGD peptides and biodistribution", INTERNATIONAL JOURNAL OF CLINICAL AND EXPERIMENTAL MEDICINE 2015, E-CENTURY PUBLISHING CORPORATION, US, vol. 5, no. 2, 1 January 2012 (2012-01-01), US , pages 165 - 172, XP093103890, ISSN: 1940-5901
BLOM ELISABETH, VELIKYAN IRINA, MONAZZAM AZITA, RAZIFAR PASHA, NAIR MANOJ, RAZIFAR PAYAM, VANDERHEYDEN JEAN‐LUC, KRIVOSHEIN ARCADI: "Synthesis and characterization of scVEGF‐PEG‐[ 68 Ga]NOTA and scVEGF‐PEG‐[ 68 Ga]DOTA PET tracers", JOURNAL OF LABELLED COMPOUNDS AND RADIOPHARMACEUTICALS, JOHN WILEY & SONS LTD., GB, vol. 54, no. 11, 1 September 2011 (2011-09-01), GB , pages 685 - 692, XP093103899, ISSN: 0362-4803, DOI: 10.1002/jlcr.1909
VELIKYAN IRINA, SUNDIN ANDERS, ERIKSSON BARBRO, LUNDQVIST HANS, SÖRENSEN JENS, BERGSTRÖM MATS, LÅNGSTRÖM BENGT: "In vivo binding of [68Ga]-DOTATOC to somatostatin receptors in neuroendocrine tumours — impact of peptide mass", NUCLEAR MEDICINE AND BIOLOGY, ELSEVIER, NY., US, vol. 37, no. 3, 1 April 2010 (2010-04-01), US , pages 265 - 275, XP093103902, ISSN: 0969-8051, DOI: 10.1016/j.nucmedbio.2009.11.008
BLOM E., LÅNGSTRÖM B., VELIKYAN I.: "68Ga-Labeling of Biotin Analogues and their Characterization", BIOCONJUGATE CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 20, no. 6, 17 June 2009 (2009-06-17), US , pages 1146 - 1151, XP002612277, ISSN: 1043-1802, DOI: 10.1021/bc800538s
VELIKYAN, I. ; BEYER, G.J. ; BERGSTROM-PETTERMANN, E. ; JOHANSEN, P. ; BERGSTROM, M. ; LANGSTROM, B.: "The importance of high specific radioactivity in the performance of ^6^8Ga-labeled peptide", NUCLEAR MEDICINE AND BIOLOGY, ELSEVIER, NY., US, vol. 35, no. 5, 1 July 2008 (2008-07-01), US , pages 529 - 536, XP022851413, ISSN: 0969-8051, DOI: 10.1016/j.nucmedbio.2008.03.002
VELIKYAN I, ET AL: "Preparation and evaluation of <68>Ga-DOTA-hEGF for visualization of EGFR expression in malignant tumors", THE JOURNAL OF NUCLEAR MEDICINE, SOCIETY OF NUCLEAR MEDICINE, US, vol. 46, no. 11, 1 November 2005 (2005-11-01), US , pages 1881 - 1888, XP002469872, ISSN: 0161-5505
VELIKYAN I., LENDVAI G., VÄLILÄ M., ROIVAINEN A., YNGVE U., BERGSTRÖM M., LÅNGSTRÖM B.: "Microwave accelerated 68 Ga‐labelling of oligonucleotides", JOURNAL OF LABELLED COMPOUNDS AND RADIOPHARMACEUTICALS, JOHN WILEY & SONS LTD., GB, vol. 47, no. 1, 1 January 2004 (2004-01-01), GB , pages 79 - 89, XP093103909, ISSN: 0362-4803, DOI: 10.1002/jlcr.799
PARK SANG HYUN, HUI JEONG GWON, SEUNG HO JANG: "Microwave-assisted rapid synthesis of 166Ho-1,4,7,10-tetraazacyclododecane-N,N',N'',N'''-tetraacetic acid: a bifunctional chelating agent for radiopharmaceuticals", ASIAN JOURNAL OF CHEMISTRY, vol. 19, no. 1, 1 January 2007 (2007-01-01), pages 391 - 395, XP093103916
KUO HSIOU-TING, PAN JINHE, ZHANG ZHENGXING, LAU JOSEPH, MERKENS HELEN, ZHANG CHENGCHENG, COLPO NADINE, LIN KUO-SHYAN, BÉNARD FRANÇ: "Effects of Linker Modification on Tumor-to-Kidney Contrast of 68 Ga-Labeled PSMA-Targeted Imaging Probes", MOLECULAR PHARMACEUTICS, AMERICAN CHEMICAL SOCIETY, US, vol. 15, no. 8, 6 August 2018 (2018-08-06), US , pages 3502 - 3511, XP093103875, ISSN: 1543-8384, DOI: 10.1021/acs.molpharmaceut.8b00499
SANO KOHEI, OKADA MAYUMI, HISADA HAYATO, SHIMOKAWA KENTA, SAJI HIDEO, MAEDA MINORU, MUKAI TAKAHIRO: "In Vivo Evaluation of a Radiogallium-Labeled Bifunctional Radiopharmaceutical, Ga-DOTA-MN2, for Hypoxic Tumor Imaging", BIOLOGICAL & PHARMACEUTICAL BULLETIN, PHARMACEUTICAL SOCIETY OF JAPAN, TOKYO., JP, vol. 36, no. 4, 1 January 2013 (2013-01-01), JP , pages 602 - 608, XP093103880, ISSN: 0918-6158, DOI: 10.1248/bpb.b12-00982
YANG ZHI, XIONG CHIYI, ZHANG RUI, ZHU HUA, LI CHUN: "Synthesis and evaluation of 68 Ga-labeled DOTA-2-deoxy-D-glucosamine as a potential radiotracer in µPET imaging", AMERICAN JOURNAL OF NUCLEAR MEDICINE AND MOLECULAR IMAGING, E-CENTURY PUBLISHING CORPORATION, US, vol. 2, no. 4, 30 October 2012 (2012-10-30), US , pages 499 - 507, XP093103882, ISSN: 2160-8407
YANG ZHI, ZHU HUA: "Synthesis and Evaluation of New Nuclides Ga-68 Labeled D-Glucose for Potential PET Imaging Agent", ACTA CHIMICA SINICA, ZHONGGUO KEXUEYUAN SHANGHAI YOUJI HUAXUE YANJIUSUO, CN, vol. 70, no. 9, 1 July 2012 (2012-07-01), CN , pages 1066 - 1072, XP093103888, ISSN: 0567-7351
BLOM ELISABETH, VELIKYAN IRINA, ESTRADA SERGIO, HALL HÅKAN, MUHAMMAD TAJ, DING CHENMIN, NAIR MANOJ, LÅNGSTRÖM BENGT: "68Ga-Labeling of RGD peptides and biodistribution", INTERNATIONAL JOURNAL OF CLINICAL AND EXPERIMENTAL MEDICINE 2015, E-CENTURY PUBLISHING CORPORATION, US, vol. 5, no. 2, 1 January 2012 (2012-01-01), US , pages 165 - 172, XP093103890, ISSN: 1940-5901
BLOM ELISABETH, VELIKYAN IRINA, MONAZZAM AZITA, RAZIFAR PASHA, NAIR MANOJ, RAZIFAR PAYAM, VANDERHEYDEN JEAN‐LUC, KRIVOSHEIN ARCADI: "Synthesis and characterization of scVEGF‐PEG‐[ 68 Ga]NOTA and scVEGF‐PEG‐[ 68 Ga]DOTA PET tracers", JOURNAL OF LABELLED COMPOUNDS AND RADIOPHARMACEUTICALS, JOHN WILEY & SONS LTD., GB, vol. 54, no. 11, 1 September 2011 (2011-09-01), GB , pages 685 - 692, XP093103899, ISSN: 0362-4803, DOI: 10.1002/jlcr.1909
VELIKYAN IRINA, SUNDIN ANDERS, ERIKSSON BARBRO, LUNDQVIST HANS, SÖRENSEN JENS, BERGSTRÖM MATS, LÅNGSTRÖM BENGT: "In vivo binding of [68Ga]-DOTATOC to somatostatin receptors in neuroendocrine tumours — impact of peptide mass", NUCLEAR MEDICINE AND BIOLOGY, ELSEVIER, NY., US, vol. 37, no. 3, 1 April 2010 (2010-04-01), US , pages 265 - 275, XP093103902, ISSN: 0969-8051, DOI: 10.1016/j.nucmedbio.2009.11.008
BLOM E., LÅNGSTRÖM B., VELIKYAN I.: "68Ga-Labeling of Biotin Analogues and their Characterization", BIOCONJUGATE CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 20, no. 6, 17 June 2009 (2009-06-17), US , pages 1146 - 1151, XP002612277, ISSN: 1043-1802, DOI: 10.1021/bc800538s
VELIKYAN, I. ; BEYER, G.J. ; BERGSTROM-PETTERMANN, E. ; JOHANSEN, P. ; BERGSTROM, M. ; LANGSTROM, B.: "The importance of high specific radioactivity in the performance of ^6^8Ga-labeled peptide", NUCLEAR MEDICINE AND BIOLOGY, ELSEVIER, NY., US, vol. 35, no. 5, 1 July 2008 (2008-07-01), US , pages 529 - 536, XP022851413, ISSN: 0969-8051, DOI: 10.1016/j.nucmedbio.2008.03.002
VELIKYAN I, ET AL: "Preparation and evaluation of <68>Ga-DOTA-hEGF for visualization of EGFR expression in malignant tumors", THE JOURNAL OF NUCLEAR MEDICINE, SOCIETY OF NUCLEAR MEDICINE, US, vol. 46, no. 11, 1 November 2005 (2005-11-01), US , pages 1881 - 1888, XP002469872, ISSN: 0161-5505
VELIKYAN I., LENDVAI G., VÄLILÄ M., ROIVAINEN A., YNGVE U., BERGSTRÖM M., LÅNGSTRÖM B.: "Microwave accelerated 68 Ga‐labelling of oligonucleotides", JOURNAL OF LABELLED COMPOUNDS AND RADIOPHARMACEUTICALS, JOHN WILEY & SONS LTD., GB, vol. 47, no. 1, 1 January 2004 (2004-01-01), GB , pages 79 - 89, XP093103909, ISSN: 0362-4803, DOI: 10.1002/jlcr.799
PARK SANG HYUN, HUI JEONG GWON, SEUNG HO JANG: "Microwave-assisted rapid synthesis of 166Ho-1,4,7,10-tetraazacyclododecane-N,N',N'',N'''-tetraacetic acid: a bifunctional chelating agent for radiopharmaceuticals", ASIAN JOURNAL OF CHEMISTRY, vol. 19, no. 1, 1 January 2007 (2007-01-01), pages 391 - 395, XP093103916
Attorney, Agent or Firm:
SHOWA INTERNATIONAL PATENT FIRM (JP)
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