Title:
HIGH-PURITY COPPER RADIOPHARMACEUTICAL COMPOSITIONS AND DIAGNOSTIC AND THERAPEUTIC USES THEREOF
Document Type and Number:
WIPO Patent Application WO/2024/064969
Kind Code:
A3
Abstract:
The present disclosure relates to the field of nuclear imaging and therapy, and more specifically to high purity copper radiotracer compositions useful in imaging, such as positron emission tomography (PET) and single-photon emission computerized tomography (SPECT), and therapy. More specifically, the present disclosure relates to novel compositions useful in imaging and treatment of conditions such as prostate cancer, somatostatin receptor-expressing tumors, like neuroendocrine tumor, epithelial tumors, as well as to methods wherein such compositions are prepared.
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Inventors:
JAAFAR-THIEL LEILA (CH)
FANI MELPOMENI (CH)
MILLUL JACOPO (CH)
DE ROSE FRANCESCO (CH)
FANI MELPOMENI (CH)
MILLUL JACOPO (CH)
DE ROSE FRANCESCO (CH)
Application Number:
PCT/US2023/075067
Publication Date:
May 16, 2024
Filing Date:
September 25, 2023
Export Citation:
Assignee:
NUCLIDIUM AG (CH)
UNIV OF BASEL (CH)
MORALES CARL A (US)
UNIV OF BASEL (CH)
MORALES CARL A (US)
International Classes:
A61K51/04; A61K51/08; A61P35/00; A61K103/00; C07B59/00; C07F1/08
Domestic Patent References:
| WO2018215627A1 | 2018-11-29 | |||
| WO2021225760A1 | 2021-11-11 | |||
| WO2022266499A1 | 2022-12-22 | |||
| WO2019154886A1 | 2019-08-15 | |||
| WO2021160825A1 | 2021-08-19 | |||
| WO2022212958A1 | 2022-10-06 | |||
| WO2023144379A1 | 2023-08-03 | |||
| WO2023057457A1 | 2023-04-13 |
Other References:
BASACO BERNABEU T. ET AL: "61Cu-PSMA versus 68Ga-PSMA for PET imaging of prostate cancer", EUROPEAN JOURNAL OF NUCLEAR MEDICINE AND MOLECULAR IMAGING, vol. 48, no. supplement 1, 20 October 2021 (2021-10-20), pages S20 - S21, XP093110702
BASACO BERNABEU T. ET AL: "61Cu-PSMA: a new radiotracer for PET imaging of prostate cancer", EUROPEAN JOURNAL OF NUCLEAR MEDICINE AND MOLECULAR IMAGING, vol. 48, no. supplement 1, 20 October 2021 (2021-10-20), pages S15, XP093110593
WEINEISEN MARTINA ET AL: "68 Ga- and 177 Lu-Labeled PSMA I&T: Optimization of a PSMA-Targeted Theranostic Concept and First Proof-of-Concept Human Studies", THE JOURNAL OF NUCLEAR MEDICINE, vol. 56, no. 8, 1 August 2015 (2015-08-01), US, pages 1169 - 1176, XP055919654, ISSN: 0161-5505, Retrieved from the Internet DOI: 10.2967/jnumed.115.158550
AHMEDOVA ANIFE ET AL: "Copper radiopharmaceuticals for theranostic applications", EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, ELSEVIER, AMSTERDAM, NL, vol. 157, 23 August 2018 (2018-08-23), pages 1406 - 1425, XP085491776, ISSN: 0223-5234, DOI: 10.1016/J.EJMECH.2018.08.051
SVEDJEHED JOHAN ET AL: "Automated, cassette-based isolation and formulation of high-purity [61Cu]CuCl2 from solid Ni targets", EJNMMI RADIOPHARMACY AND CHEMISTRY, vol. 5, no. 1, 5 November 2020 (2020-11-05), XP093109943, ISSN: 2365-421X, Retrieved from the Internet DOI: 10.1186/s41181-020-00108-7
KELLY JAMES M. ET AL: "Preclinical Evaluation of a High-Affinity Sarcophagine-Containing PSMA Ligand for 64 Cu/ 67 Cu-Based Theranostics in Prostate Cancer", MOLECULAR PHARMACEUTICS, vol. 17, no. 6, 1 June 2020 (2020-06-01), US, pages 1954 - 1962, XP055906297, ISSN: 1543-8384, Retrieved from the Internet DOI: 10.1021/acs.molpharmaceut.0c00060
NAMBISAN A ET AL: "Preclinical evaluation of 67Cu-PSMA-617 theranostic as an alternative to 177Lu-PSMA-617 for prostate cancer | Journal of Nuclear Medicine", THE JOURNAL OF NUCLEAR MEDICINE, 1 June 2022 (2022-06-01), pages 1 - 5, XP093110604, Retrieved from the Internet [retrieved on 20231209]
ELENI GOURNI ET AL: "Metal-Based PSMA Radioligands", MOLECULES, vol. 22, no. 4, 24 March 2017 (2017-03-24), pages 523, XP055580174, DOI: 10.3390/molecules22040523
BANERJEE SANGEETA RAY ET AL: "64 Cu-Labeled Inhibitors of Prostate-Specific Membrane Antigen for PET Imaging of Prostate Cancer", JOURNAL OF MEDICINAL CHEMISTRY, vol. 57, no. 6, 7 March 2014 (2014-03-07), US, pages 2657 - 2669, XP093110556, ISSN: 0022-2623, DOI: 10.1021/jm401921j
ELENI GOURNI ET AL: "(R)-NODAGA-PSMA: A Versatile Precursor for Radiometal Labeling and Nuclear Imaging of PSMA-Positive Tumors", PLOS ONE, vol. 10, no. 12, 23 December 2015 (2015-12-23), pages e0145755, XP055289287, DOI: 10.1371/journal.pone.0145755
ZHANG YIN ET AL: "Positron Emission Tomography Imaging of Vascular Endothelial Growth Factor Receptor Expression with 61 Cu-Labeled Lysine-Tagged VEGF 121", MOLECULAR PHARMACEUTICS, vol. 9, no. 12, 16 November 2012 (2012-11-16), US, pages 3586 - 3594, XP093110221, ISSN: 1543-8384, DOI: 10.1021/mp3005269
BASACO BERNABEU T. ET AL: "61Cu-PSMA PET in prostate cancer: development and selection of the first radioligand for clinical translation", EUROPEAN JOURNAL OF NUCLEAR MEDICINE AND MOLECULAR IMAGING 20230901 SPRINGER BERLIN HEIDELBERG NLD, vol. 50, no. Suppl. 1, 1 September 2023 (2023-09-01), Berlin, DE, pages S425 - S426, XP093110599, ISSN: 1619-7089
ZANDI NADIA: "61Cu/67Cu theranostic pair production, chemical separation and radiolabeling -", 29 October 2021 (2021-10-29), pages 1 - 183, XP093110603, Retrieved from the Internet DOI: 10.48549/3234
FONSECA ALEXANDRA I. ET AL: "Production of GMP-Compliant Clinical Amounts of Copper-61 Radiopharmaceuticals from Liquid Targets", PHARMACEUTICALS, vol. 15, no. 6, 7 June 2022 (2022-06-07), CH, pages 723, XP093110536, ISSN: 1424-8247, DOI: 10.3390/ph15060723
WEN PING LI ET AL: "DOTA-D-Tyr1-Octreotate: A Somatostatin Analogue for Labeling with Metal and Halogen Radionuclides for Cancer Imaging and Therapy", BIOCONJUGATE CHEMISTRY, vol. 13, no. 4, 1 July 2002 (2002-07-01), pages 721 - 728, XP055164016, ISSN: 1043-1802, DOI: 10.1021/bc015590k
MARCINIAK ALEKSANDRA ET AL: "Somatostatin analogues labeled with copper radioisotopes: current status", JOURNAL OF RADIOANALYTICAL AND NUCLEAR CHEMISTRY, vol. 313, no. 2, 13 June 2017 (2017-06-13), HU, pages 279 - 289, XP093140572, ISSN: 0236-5731, Retrieved from the Internet DOI: 10.1007/s10967-017-5323-x
CULLINANE CARLEEN ET AL: "Peptide Receptor Radionuclide Therapy with 67 Cu-CuSarTATE Is Highly Efficacious Against a Somatostatin-Positive Neuroendocrine Tumor Model", THE JOURNAL OF NUCLEAR MEDICINE, vol. 61, no. 12, 1 December 2020 (2020-12-01), US, pages 1800 - 1805, XP093140535, ISSN: 0161-5505, Retrieved from the Internet DOI: 10.2967/jnumed.120.243543
A. PFEIFER ET AL: "Clinical PET of Neuroendocrine Tumors Using 64Cu-DOTATATE: First-in-Humans Study", THE JOURNAL OF NUCLEAR MEDICINE, vol. 53, no. 8, 10 July 2012 (2012-07-10), pages 1207 - 1215, XP055163911, ISSN: 0161-5505, DOI: 10.2967/jnumed.111.101469
NEDROW JESSIE R. ET AL: "Positron Emission Tomographic Imaging of Copper 64- and Gallium 68-Labeled Chelator Conjugates of the Somatostatin Agonist Tyr 3 -Octreotate", MOLECULAR IMAGING, vol. 13, no. 7, 1 September 2014 (2014-09-01), XP093139785, ISSN: 1536-0121, Retrieved from the Internet DOI: 10.2310/7290.2014.00020
M. FANI ET AL: "PET of Somatostatin Receptor-Positive Tumors Using 64Cu- and 68Ga-Somatostatin Antagonists: The Chelate Makes the Difference", THE JOURNAL OF NUCLEAR MEDICINE, vol. 52, no. 7, 16 June 2011 (2011-06-16), US, pages 1110 - 1118, XP055282970, ISSN: 0161-5505, DOI: 10.2967/jnumed.111.087999
RYLOVA SVETLANA N. ET AL: "The somatostatin receptor 2 antagonist 64Cu-NODAGA-JR11 outperforms 64Cu-DOTA-TATE in a mouse xenograft model", PLOS ONE, vol. 13, no. 4, 18 April 2018 (2018-04-18), US, pages e0195802, XP093110360, ISSN: 1932-6203, DOI: 10.1371/journal.pone.0195802
EISENWIENER K-P ET AL: "NODAGATOC, A NEW CHELATOR-COUPLED SOMATOSTATIN ANALOGUE LABELED WITH 67/68Ga AND 111In FOR SPECT, PET, AND TARGETED THERAPEUTIC APPLICATIONS OF SOMATOSTATIN RECEPTOR (HSST2) EXPRESSING TUMORS", BIOCONJUGATE CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 13, no. 3, 1 May 2002 (2002-05-01), pages 530 - 541, XP001172818, ISSN: 1043-1802, DOI: 10.1021/BC010074F
SVEDJEHED J. ET AL: "New extractant-impregnated iTLC-SG paper facilitates improved TLC analysis for Cu radiolabelled peptides", NUCLEAR MEDICINE AND BIOLOGY - ABSTRACTS OF THE FOURTH INTERNATIONAL SYMPOSIUM ON TECHNETIUM AND OTHER RADIOMETALS IN CHEMISTRY AND MEDICINE (TERACHEM 2022) 14-17 SEPTEMBER 2022 - BRESSANONE, ITALY, 1 November 2022 (2022-11-01), pages S72, XP093140922, Retrieved from the Internet [retrieved on 20240313]
WATABE TADASHI ET AL: "Theranostics Targeting Fibroblast Activation Protein in the Tumor Stroma: 64 Cu- and 225 Ac-Labeled FAPI-04 in Pancreatic Cancer Xenograft Mouse Models", THE JOURNAL OF NUCLEAR MEDICINE, vol. 61, no. 4, 4 October 2019 (2019-10-04), US, pages 563 - 569, XP093142049, ISSN: 0161-5505, DOI: 10.2967/jnumed.119.233122
LOKTEV ANASTASIA ET AL: "Development of Fibroblast Activation Protein-Targeted Radiotracers with Improved Tumor Retention", THE JOURNAL OF NUCLEAR MEDICINE, vol. 60, no. 10, 1 October 2019 (2019-10-01), US, pages 1421 - 1429, XP093142050, ISSN: 0161-5505, Retrieved from the Internet DOI: 10.2967/jnumed.118.224469
LINDNER THOMAS ET AL: "Development of Quinoline-Based Theranostic Ligands for the Targeting of Fibroblast Activation Protein", THE JOURNAL OF NUCLEAR MEDICINE, vol. 59, no. 9, 6 April 2018 (2018-04-06), US, pages 1415 - 1422, XP093142082, ISSN: 0161-5505, DOI: 10.2967/jnumed.118.210443
HESTERMAN J. ET AL: "Preclinical characterization of novel radiolabeled and fluorescent-labeled Fibroblast Activation Protein (FAP)- targeting ligands using gamma counting, SPECT imaging and Cryo-Fluorescence Tomography (CFT)", EUROPEAN JOURNAL OF NUCLEAR MEDICINE AND MOLECULAR IMAGING, vol. 50, no. Supplement 1, 1 September 2023 (2023-09-01), pages S424 - S425, XP093112913
MILLUL J ET AL: "Enhancing the tumor-to-background ratio of FAP-positive PET/CT scans with the novel <61>Cu- Kalios derivatives: synthesis, in vitro and in vivo characterization", EUROPEAN JOURNAL OF NUCLEAR MEDICINE AND MOLECULAR IMAGING, vol. 50, no. Supplement 1, 1 September 2023 (2023-09-01), Berlin, DE, pages S186, XP093110601, ISSN: 1619-7089
BASACO BERNABEU T. ET AL: "61Cu-PSMA: a new radiotracer for PET imaging of prostate cancer", EUROPEAN JOURNAL OF NUCLEAR MEDICINE AND MOLECULAR IMAGING, vol. 48, no. supplement 1, 20 October 2021 (2021-10-20), pages S15, XP093110593
WEINEISEN MARTINA ET AL: "68 Ga- and 177 Lu-Labeled PSMA I&T: Optimization of a PSMA-Targeted Theranostic Concept and First Proof-of-Concept Human Studies", THE JOURNAL OF NUCLEAR MEDICINE, vol. 56, no. 8, 1 August 2015 (2015-08-01), US, pages 1169 - 1176, XP055919654, ISSN: 0161-5505, Retrieved from the Internet
AHMEDOVA ANIFE ET AL: "Copper radiopharmaceuticals for theranostic applications", EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, ELSEVIER, AMSTERDAM, NL, vol. 157, 23 August 2018 (2018-08-23), pages 1406 - 1425, XP085491776, ISSN: 0223-5234, DOI: 10.1016/J.EJMECH.2018.08.051
SVEDJEHED JOHAN ET AL: "Automated, cassette-based isolation and formulation of high-purity [61Cu]CuCl2 from solid Ni targets", EJNMMI RADIOPHARMACY AND CHEMISTRY, vol. 5, no. 1, 5 November 2020 (2020-11-05), XP093109943, ISSN: 2365-421X, Retrieved from the Internet
KELLY JAMES M. ET AL: "Preclinical Evaluation of a High-Affinity Sarcophagine-Containing PSMA Ligand for 64 Cu/ 67 Cu-Based Theranostics in Prostate Cancer", MOLECULAR PHARMACEUTICS, vol. 17, no. 6, 1 June 2020 (2020-06-01), US, pages 1954 - 1962, XP055906297, ISSN: 1543-8384, Retrieved from the Internet
NAMBISAN A ET AL: "Preclinical evaluation of 67Cu-PSMA-617 theranostic as an alternative to 177Lu-PSMA-617 for prostate cancer | Journal of Nuclear Medicine", THE JOURNAL OF NUCLEAR MEDICINE, 1 June 2022 (2022-06-01), pages 1 - 5, XP093110604, Retrieved from the Internet
ELENI GOURNI ET AL: "Metal-Based PSMA Radioligands", MOLECULES, vol. 22, no. 4, 24 March 2017 (2017-03-24), pages 523, XP055580174, DOI: 10.3390/molecules22040523
BANERJEE SANGEETA RAY ET AL: "64 Cu-Labeled Inhibitors of Prostate-Specific Membrane Antigen for PET Imaging of Prostate Cancer", JOURNAL OF MEDICINAL CHEMISTRY, vol. 57, no. 6, 7 March 2014 (2014-03-07), US, pages 2657 - 2669, XP093110556, ISSN: 0022-2623, DOI: 10.1021/jm401921j
ELENI GOURNI ET AL: "(R)-NODAGA-PSMA: A Versatile Precursor for Radiometal Labeling and Nuclear Imaging of PSMA-Positive Tumors", PLOS ONE, vol. 10, no. 12, 23 December 2015 (2015-12-23), pages e0145755, XP055289287, DOI: 10.1371/journal.pone.0145755
ZHANG YIN ET AL: "Positron Emission Tomography Imaging of Vascular Endothelial Growth Factor Receptor Expression with 61 Cu-Labeled Lysine-Tagged VEGF 121", MOLECULAR PHARMACEUTICS, vol. 9, no. 12, 16 November 2012 (2012-11-16), US, pages 3586 - 3594, XP093110221, ISSN: 1543-8384, DOI: 10.1021/mp3005269
BASACO BERNABEU T. ET AL: "61Cu-PSMA PET in prostate cancer: development and selection of the first radioligand for clinical translation", EUROPEAN JOURNAL OF NUCLEAR MEDICINE AND MOLECULAR IMAGING 20230901 SPRINGER BERLIN HEIDELBERG NLD, vol. 50, no. Suppl. 1, 1 September 2023 (2023-09-01), Berlin, DE, pages S425 - S426, XP093110599, ISSN: 1619-7089
ZANDI NADIA: "61Cu/67Cu theranostic pair production, chemical separation and radiolabeling -", 29 October 2021 (2021-10-29), pages 1 - 183, XP093110603, Retrieved from the Internet
FONSECA ALEXANDRA I. ET AL: "Production of GMP-Compliant Clinical Amounts of Copper-61 Radiopharmaceuticals from Liquid Targets", PHARMACEUTICALS, vol. 15, no. 6, 7 June 2022 (2022-06-07), CH, pages 723, XP093110536, ISSN: 1424-8247, DOI: 10.3390/ph15060723
WEN PING LI ET AL: "DOTA-D-Tyr1-Octreotate: A Somatostatin Analogue for Labeling with Metal and Halogen Radionuclides for Cancer Imaging and Therapy", BIOCONJUGATE CHEMISTRY, vol. 13, no. 4, 1 July 2002 (2002-07-01), pages 721 - 728, XP055164016, ISSN: 1043-1802, DOI: 10.1021/bc015590k
MARCINIAK ALEKSANDRA ET AL: "Somatostatin analogues labeled with copper radioisotopes: current status", JOURNAL OF RADIOANALYTICAL AND NUCLEAR CHEMISTRY, vol. 313, no. 2, 13 June 2017 (2017-06-13), HU, pages 279 - 289, XP093140572, ISSN: 0236-5731, Retrieved from the Internet
CULLINANE CARLEEN ET AL: "Peptide Receptor Radionuclide Therapy with 67 Cu-CuSarTATE Is Highly Efficacious Against a Somatostatin-Positive Neuroendocrine Tumor Model", THE JOURNAL OF NUCLEAR MEDICINE, vol. 61, no. 12, 1 December 2020 (2020-12-01), US, pages 1800 - 1805, XP093140535, ISSN: 0161-5505, Retrieved from the Internet
A. PFEIFER ET AL: "Clinical PET of Neuroendocrine Tumors Using 64Cu-DOTATATE: First-in-Humans Study", THE JOURNAL OF NUCLEAR MEDICINE, vol. 53, no. 8, 10 July 2012 (2012-07-10), pages 1207 - 1215, XP055163911, ISSN: 0161-5505, DOI: 10.2967/jnumed.111.101469
NEDROW JESSIE R. ET AL: "Positron Emission Tomographic Imaging of Copper 64- and Gallium 68-Labeled Chelator Conjugates of the Somatostatin Agonist Tyr 3 -Octreotate", MOLECULAR IMAGING, vol. 13, no. 7, 1 September 2014 (2014-09-01), XP093139785, ISSN: 1536-0121, Retrieved from the Internet
M. FANI ET AL: "PET of Somatostatin Receptor-Positive Tumors Using 64Cu- and 68Ga-Somatostatin Antagonists: The Chelate Makes the Difference", THE JOURNAL OF NUCLEAR MEDICINE, vol. 52, no. 7, 16 June 2011 (2011-06-16), US, pages 1110 - 1118, XP055282970, ISSN: 0161-5505, DOI: 10.2967/jnumed.111.087999
RYLOVA SVETLANA N. ET AL: "The somatostatin receptor 2 antagonist 64Cu-NODAGA-JR11 outperforms 64Cu-DOTA-TATE in a mouse xenograft model", PLOS ONE, vol. 13, no. 4, 18 April 2018 (2018-04-18), US, pages e0195802, XP093110360, ISSN: 1932-6203, DOI: 10.1371/journal.pone.0195802
EISENWIENER K-P ET AL: "NODAGATOC, A NEW CHELATOR-COUPLED SOMATOSTATIN ANALOGUE LABELED WITH 67/68Ga AND 111In FOR SPECT, PET, AND TARGETED THERAPEUTIC APPLICATIONS OF SOMATOSTATIN RECEPTOR (HSST2) EXPRESSING TUMORS", BIOCONJUGATE CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 13, no. 3, 1 May 2002 (2002-05-01), pages 530 - 541, XP001172818, ISSN: 1043-1802, DOI: 10.1021/BC010074F
SVEDJEHED J. ET AL: "New extractant-impregnated iTLC-SG paper facilitates improved TLC analysis for Cu radiolabelled peptides", NUCLEAR MEDICINE AND BIOLOGY - ABSTRACTS OF THE FOURTH INTERNATIONAL SYMPOSIUM ON TECHNETIUM AND OTHER RADIOMETALS IN CHEMISTRY AND MEDICINE (TERACHEM 2022) 14-17 SEPTEMBER 2022 - BRESSANONE, ITALY, 1 November 2022 (2022-11-01), pages S72, XP093140922, Retrieved from the Internet
WATABE TADASHI ET AL: "Theranostics Targeting Fibroblast Activation Protein in the Tumor Stroma: 64 Cu- and 225 Ac-Labeled FAPI-04 in Pancreatic Cancer Xenograft Mouse Models", THE JOURNAL OF NUCLEAR MEDICINE, vol. 61, no. 4, 4 October 2019 (2019-10-04), US, pages 563 - 569, XP093142049, ISSN: 0161-5505, DOI: 10.2967/jnumed.119.233122
LOKTEV ANASTASIA ET AL: "Development of Fibroblast Activation Protein-Targeted Radiotracers with Improved Tumor Retention", THE JOURNAL OF NUCLEAR MEDICINE, vol. 60, no. 10, 1 October 2019 (2019-10-01), US, pages 1421 - 1429, XP093142050, ISSN: 0161-5505, Retrieved from the Internet
LINDNER THOMAS ET AL: "Development of Quinoline-Based Theranostic Ligands for the Targeting of Fibroblast Activation Protein", THE JOURNAL OF NUCLEAR MEDICINE, vol. 59, no. 9, 6 April 2018 (2018-04-06), US, pages 1415 - 1422, XP093142082, ISSN: 0161-5505, DOI: 10.2967/jnumed.118.210443
HESTERMAN J. ET AL: "Preclinical characterization of novel radiolabeled and fluorescent-labeled Fibroblast Activation Protein (FAP)- targeting ligands using gamma counting, SPECT imaging and Cryo-Fluorescence Tomography (CFT)", EUROPEAN JOURNAL OF NUCLEAR MEDICINE AND MOLECULAR IMAGING, vol. 50, no. Supplement 1, 1 September 2023 (2023-09-01), pages S424 - S425, XP093112913
MILLUL J ET AL: "Enhancing the tumor-to-background ratio of FAP-positive PET/CT scans with the novel <61>Cu- Kalios derivatives: synthesis, in vitro and in vivo characterization", EUROPEAN JOURNAL OF NUCLEAR MEDICINE AND MOLECULAR IMAGING, vol. 50, no. Supplement 1, 1 September 2023 (2023-09-01), Berlin, DE, pages S186, XP093110601, ISSN: 1619-7089
Attorney, Agent or Firm:
MORALES, Carl A. et al. (US)
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