Title:
[11C]-LABELLED ACYCLIC RETINOID, CENTRAL NERVOUS SYSTEM ACTIVATOR, AND PRODUCTION METHODS FOR SAME
Document Type and Number:
WIPO Patent Application WO/2022/107865
Kind Code:
A1
Abstract:
[Problem] To provide a 11C-labelled acyclic retinoid that can be efficiently synthesized in a short amount of time and is suited to elucidating intracerebral kinetics using PET, a PET probe that uses the retinoid, and production methods for the retinoid and the PET probe. [Solution] This 11C-labelled acyclic retinoid is characterized by being represented by chemical formula (a). The compound can be produced by means of a coupling process in which methyl iodide that has been labelled with 11C and organic tin compound (b) (in the formula, R1 and R2 represent alkyl groups that may be branched) are cross-coupled in an aprotic solvent in the presence of a palladium complex, a phosphine ligand, and a copper(I) halide.
Inventors:
SUZUKI MASAAKI (JP)
ITO KENGO (JP)
KIMURA YASUYUKI (JP)
OGATA AYA (JP)
IKENUMA HIROSHI (JP)
KIMURA TETSUYA (JP)
KIMURA NOBUYUKI (JP)
KOYAMA HIROKO (JP)
ISHII HIDEKI (JP)
CHO MEIEI (JP)
KAWAMURA KAZUNORI (JP)
MINAMIMOTO TAKAFUMI (JP)
NAGAI YUJI (JP)
KATSUKI HIROSHI (JP)
ITO KENGO (JP)
KIMURA YASUYUKI (JP)
OGATA AYA (JP)
IKENUMA HIROSHI (JP)
KIMURA TETSUYA (JP)
KIMURA NOBUYUKI (JP)
KOYAMA HIROKO (JP)
ISHII HIDEKI (JP)
CHO MEIEI (JP)
KAWAMURA KAZUNORI (JP)
MINAMIMOTO TAKAFUMI (JP)
NAGAI YUJI (JP)
KATSUKI HIROSHI (JP)
Application Number:
PCT/JP2021/042503
Publication Date:
May 27, 2022
Filing Date:
November 18, 2021
Export Citation:
Assignee:
NAT CT GERIATRICS & GERONTOLOGY (JP)
International Classes:
A61P25/00; A61K31/202; A61K51/04; C07B61/00; C07C51/09; C07C57/03; C07C67/343; C07C69/587; C07C403/20
Foreign References:
| JP2013540762A | 2013-11-07 | |||
| JPS56140949A | 1981-11-04 | |||
| JP2004331654A | 2004-11-25 | |||
| JP2001002621A | 2001-01-09 | |||
| JPS56140949A | 1981-11-04 |
Other References:
SUZUKI MASAAKI; TAKASHIMA-HIRANO MISATO; ISHII HIDEKI; WATANABE CHIKA; SUMI KENGO; KOYAMA HIROKO; DOI HISASHI: "Synthesis of11C-labeled retinoic acid, [11C]ATRA, via an alkenylboron precursor by Pd(0)-mediated rapidC-[11C]methylation", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, ELSEVIER, AMSTERDAM, NL, vol. 24, no. 15, 2 June 2014 (2014-06-02), AMSTERDAM, NL , pages 3622 - 3625, XP028864091, ISSN: 0960-894X, DOI: 10.1016/j.bmcl.2014.05.041
SUZUKI MASAAKI: "Fast methylation reaction that renews the PET tracer synthesis base. Visualization of prostaglandin receptors", KAGAKU TO SEIBUTSU, 1 January 2005 (2005-01-01), pages 804 - 808, XP055931611, Retrieved from the Internet DOI: 10.1271/kagakutoseibutsu1962.43.804
"Diagnosis and Management in Dementia: The neuroscience of dementia ; volume 1", vol. 1, 30 October 2020, ELSEVIER, ISBN: 978-0-12-815855-5, article BEHESHTI, SIAMAK: "Chapter 35 - All-trans retinoic acid in Alzheimer's disease", pages: 559 - 572, XP009536837, DOI: 10.1016/B978-0-12-815854-8.00035-5
FUKASAWA HIROSHI, KAWAHARA KOICHI, KAGECHIKA HIROYUKI: "Preclinical and Clinical Studies of tamibarotene for treatment of Alzheimer's disease", VITAMINS, vol. 91, no. 7, 1 January 2017 (2017-01-01), JP , pages 419 - 425, XP009536888, ISSN: 0006-386X, DOI: 10.20632/vso.91.7_419
OGATA, AYA: "Search for potential of acyclic retinoid as remedy for Alzheimer's (30-37)", RESEARCH AND DEVELOPMENT COST FOR LONGEVITY MEDICAL TREATMENT. 2018 COMPREHENSIVE RESEARCH REPORT - RESEARCH AND DEVELOPMENT COST FOR LONGEVITY MEDICAL TREATMENT. 2018 COMPREHENSIVE RESEARCH REPORT, 31 March 2020 (2020-03-31), JP, pages 1 - 3, XP009537071
MASAO HONDA;TARO YAMASHITA;TATSUYA YAMASHITA;KUNIAKI ARAI;YOSHIO SAKAI;AKITO SAKAI;MIKIKO NAKAMURA;EISHIRO MIZUKOSHI;SHUICHI KANEK: "Peretinoin, an acyclic retinoid, improves the hepatic gene signature of chronic hepatitis C following curative therapy of hepatocellular carcinoma", BMC CANCER, BIOMED CENTRAL, LONDON, GB, vol. 13, no. 1, 15 April 2013 (2013-04-15), LONDON, GB , pages 191, XP021150745, ISSN: 1471-2407, DOI: 10.1186/1471-2407-13-191
SUZUKI MTAKASHIMA-HIRANO MISHII HWATANABE CSUMI KKOYAMA HDOI H, BIOORG MED CHEM LETT., vol. 243, 2014, pages 3622 - 3625
TAKASHIMA-HIRANO MISHII HSUZUKI M, ACS MED CHEM LETT., vol. 3, 2012, pages 804 - 807
0. SHIBAHARAM. WATANABES. YAMADAM. AKEHIT. SASAKIA. AKAHOSHIT. HANADAH. HIRANOS. NAKATANIH. NISHIOKA, J. MED. CHEM., vol. 60, 2017, pages 7139 - 7145
G. E. MAGOULAS, J. MED. CHEM., vol. 46, 2011, pages 721 - 737
M. SHENGMINGL. XIYAN, ORG. SYNTH., vol. 72, 1995, pages 112 - 115
SUZUKI MASAAKI: "Fast methylation reaction that renews the PET tracer synthesis base. Visualization of prostaglandin receptors", KAGAKU TO SEIBUTSU, 1 January 2005 (2005-01-01), pages 804 - 808, XP055931611, Retrieved from the Internet
"Diagnosis and Management in Dementia: The neuroscience of dementia ; volume 1", vol. 1, 30 October 2020, ELSEVIER, ISBN: 978-0-12-815855-5, article BEHESHTI, SIAMAK: "Chapter 35 - All-trans retinoic acid in Alzheimer's disease", pages: 559 - 572, XP009536837, DOI: 10.1016/B978-0-12-815854-8.00035-5
FUKASAWA HIROSHI, KAWAHARA KOICHI, KAGECHIKA HIROYUKI: "Preclinical and Clinical Studies of tamibarotene for treatment of Alzheimer's disease", VITAMINS, vol. 91, no. 7, 1 January 2017 (2017-01-01), JP , pages 419 - 425, XP009536888, ISSN: 0006-386X, DOI: 10.20632/vso.91.7_419
OGATA, AYA: "Search for potential of acyclic retinoid as remedy for Alzheimer's (30-37)", RESEARCH AND DEVELOPMENT COST FOR LONGEVITY MEDICAL TREATMENT. 2018 COMPREHENSIVE RESEARCH REPORT - RESEARCH AND DEVELOPMENT COST FOR LONGEVITY MEDICAL TREATMENT. 2018 COMPREHENSIVE RESEARCH REPORT, 31 March 2020 (2020-03-31), JP, pages 1 - 3, XP009537071
MASAO HONDA;TARO YAMASHITA;TATSUYA YAMASHITA;KUNIAKI ARAI;YOSHIO SAKAI;AKITO SAKAI;MIKIKO NAKAMURA;EISHIRO MIZUKOSHI;SHUICHI KANEK: "Peretinoin, an acyclic retinoid, improves the hepatic gene signature of chronic hepatitis C following curative therapy of hepatocellular carcinoma", BMC CANCER, BIOMED CENTRAL, LONDON, GB, vol. 13, no. 1, 15 April 2013 (2013-04-15), LONDON, GB , pages 191, XP021150745, ISSN: 1471-2407, DOI: 10.1186/1471-2407-13-191
SUZUKI MTAKASHIMA-HIRANO MISHII HWATANABE CSUMI KKOYAMA HDOI H, BIOORG MED CHEM LETT., vol. 243, 2014, pages 3622 - 3625
TAKASHIMA-HIRANO MISHII HSUZUKI M, ACS MED CHEM LETT., vol. 3, 2012, pages 804 - 807
0. SHIBAHARAM. WATANABES. YAMADAM. AKEHIT. SASAKIA. AKAHOSHIT. HANADAH. HIRANOS. NAKATANIH. NISHIOKA, J. MED. CHEM., vol. 60, 2017, pages 7139 - 7145
G. E. MAGOULAS, J. MED. CHEM., vol. 46, 2011, pages 721 - 737
M. SHENGMINGL. XIYAN, ORG. SYNTH., vol. 72, 1995, pages 112 - 115
Attorney, Agent or Firm:
AOYAMA Yo (JP)
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