Title:
TRACER COMPOSITION FOR RADIOACTIVE PET DIAGNOSIS, INTERMEDIATE THEREOF, AND PRODUCTION METHOD THEREOF
Document Type and Number:
WIPO Patent Application WO/2023/063154
Kind Code:
A1
Abstract:
[Problem] To provide: a novel tracer drug for radioactive PET diagnosis that has high accumulation properties and retention properties at a tumor site, and an efficient production method (labeling synthesis method) of the tracer drug. [Solution] A novel tracer compound having improved accumulation properties and retention properties at a tumor while maintaining high selectivity for LAT1, said tracer compound being obtained by introducing a methoxy (OMe) group into the 4-position of the benzene ring of an α-methyltyrosine (AMT) skeleton. A production method by which the aforesaid novel tracer compound can be efficiently produced at a high yield, said method employing the technique of labeling synthesis with 18F-hydrogen fluoride (18F-HF) by using a novel labeled intermediate (precursor) in which a boronic ester is introduced into the 3-position of the benzene ring of an AMT skeleton.
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Inventors:
NAKA SADAHIRO (JP)
WATABE TADASHI (JP)
KIRIHATA MITSUNORI (JP)
OHTA YOICHIRO (JP)
WATABE TADASHI (JP)
KIRIHATA MITSUNORI (JP)
OHTA YOICHIRO (JP)
Application Number:
PCT/JP2022/037004
Publication Date:
April 20, 2023
Filing Date:
October 03, 2022
Export Citation:
Assignee:
UNIV OSAKA (JP)
International Classes:
A61K45/00; A61K51/04; A61K51/00; A61P35/00; C07B61/00; C07C229/36; C07F5/02
Domestic Patent References:
| WO2019176505A1 | 2019-09-19 |
Foreign References:
| KR100706760B1 | 2007-04-13 | |||
| JP2017513930A | 2017-06-01 | |||
| GB1023204A | 1966-03-23 |
Other References:
MOON, B.S. LEE, T.S. LEE, K.C. AN, G.I. CHEON, G.J. LIM, S.M. CHOI, C.W. CHI, D.Y. CHUN, K.S.: "Syntheses of F-18 labeled fluoroalkyltyrosine derivatives and their biological evaluation in rat bearing 9L tumor", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, ELSEVIER, AMSTERDAM NL, vol. 17, no. 1, 22 December 2006 (2006-12-22), Amsterdam NL , pages 200 - 204, XP005812142, ISSN: 0960-894X, DOI: 10.1016/j.bmcl.2006.09.063
WIRIYASERMKUL PATTAMA, MORIYAMA SATOMI, KONGPRACHA PORNPARN, NAGAMORI SHUSHI: "Drug Discovery Targeting an Amino Acid Transporter for Diagnosis and Therapy", YAKUGAKU ZASSHI, vol. 141, no. 4, 31 August 2020 (2020-08-31), pages 501 - 510, XP093057908, DOI: 10.1248/yakushi.20-00204-2
HITOTSUYANAGI, Y. ISHIKAWA, H. NAITO, S. TAKEYA, K.: "Synthesis of l,l-cycloisodityrosines by copper(II) acetate-DMAP-mediated intramolecular O-arylation of phenols with phenylboronic acids", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM , NL, vol. 44, no. 31, 28 July 2003 (2003-07-28), Amsterdam , NL , pages 5901 - 5903, XP004435102, ISSN: 0040-4039, DOI: 10.1016/S0040-4039(03)01390-X
WIRIYASERMKUL PATTAMA, MORIYAMA SATOMI, KONGPRACHA PORNPARN, NAGAMORI SHUSHI: "Drug Discovery Targeting an Amino Acid Transporter for Diagnosis and Therapy", YAKUGAKU ZASSHI, vol. 141, no. 4, 31 August 2020 (2020-08-31), pages 501 - 510, XP093057908, DOI: 10.1248/yakushi.20-00204-2
HITOTSUYANAGI, Y. ISHIKAWA, H. NAITO, S. TAKEYA, K.: "Synthesis of l,l-cycloisodityrosines by copper(II) acetate-DMAP-mediated intramolecular O-arylation of phenols with phenylboronic acids", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM , NL, vol. 44, no. 31, 28 July 2003 (2003-07-28), Amsterdam , NL , pages 5901 - 5903, XP004435102, ISSN: 0040-4039, DOI: 10.1016/S0040-4039(03)01390-X
Attorney, Agent or Firm:
ONO Makoto et al. (JP)
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