Title:
11C-LABELLED O6-BENZYLGUANINE, POSITRON EMISSION TOMOGRAPHY (PET) PROBE CAPABLE OF VISUALIZING O6-METHYL GUANINE METHYL-TRANSFERASE ACTIVITY, AND PRODUCTION METHODS THEREFOR
Document Type and Number:
WIPO Patent Application WO/2018/008311
Kind Code:
A1
Abstract:
[Problem] To provide 11C-labelled O6-benzylguanine with which PET images can be obtained, and a production method therefor. [Solution] This 11C-labelled O6-benzylguanine is characterized by being represented by chemical formula (a). The compound is obtained by performing: a coupling step in which 11C-labelled methyl iodide and an organic tin compound (b) (with the caveat that, in chemical formula (b), R1 represents an alkyl group, and R2 and R3 represent elimination groups which are capable of being eliminated by bases) in an aprotic lactam are cross-coupled in the presence of a palladium complex and a phosphine ligand; and an elimination step in which elimination groups R2 and R3 of the cross-coupling product obtained as a result of the coupling step are eliminated by bases.
Inventors:
SUZUKI MASAAKI (JP)
ITO KENGO (JP)
KATO TAKASHI (JP)
IKENUMA HIROSHI (JP)
KOYAMA HIROKO (JP)
ITO KENGO (JP)
KATO TAKASHI (JP)
IKENUMA HIROSHI (JP)
KOYAMA HIROKO (JP)
Application Number:
PCT/JP2017/020728
Publication Date:
January 11, 2018
Filing Date:
June 03, 2017
Export Citation:
Assignee:
NAT CT GERIATRICS & GERONTOLOGY (JP)
International Classes:
C07D473/18; A61K51/00; C07B59/00; C07B61/00
Domestic Patent References:
| WO2010074272A1 | 2010-07-01 | |||
| WO2010074272A1 | 2010-07-01 |
Other References:
WANG,J.Q. ET AL.: "Synthesis and preliminary biological evaluation of O6-[4-(2-[18F] fluoroethoxymethyl)benzyl]guanine as a novel potential PET probe for the DNA repair protein O6-alkylguanine-DNA alkyltransferase in cancer chemotherapy", BIOORGANIC & MEDICINAL CHEMISTRY, vol. 13, 2005, pages 5779 - 5786, XP005016766
SUZUKI,M. ET AL.: "Efficient synthesis of [11C]H- 1152, a PET probe specific for Rho-kinases, highly potential targets in diagnostic medicine and drug development", TETRAHEDRON, vol. 68, no. 10, 2012, pages 2336 - 2341, XP028455631
PAULY,G.T. ET AL.: "Substitution of Aminomethyl at the Meta-Position Enhances the Inactivation of O6-Alkylguanine-DNA Alkyltransferase by 06- Benzylguanine", JOURNAL OF MEDICINAL CHEMISTRY, vol. 51, no. 22, 2008, pages 7144 - 7153, XP055563122
KOYAMA,H . ET AL.: "Synthesis of PET probe O6-[(3- [11C]methyl)benzyl]guanine by Pd°-mediated rapid C-[11C]methylation toward imaging DNA repair protein O6-methylguanine-DNA methyltransferase in glioblastoma", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 27, no. 9, 18 March 2017 (2017-03-18), pages 1892 - 1896, XP029968180
A. NATSUME; D. ISHII; T. WAKABAYASI; T. TSUNO; H. HATANO; M. MIZUNO; J. YASHIDA, CANCER RES., vol. 65, 2005, pages 7573 - 7579
A. NATSUME; T. WAKABAYASHI; D. ISHII; H. MARUTA; M. FUJII; S. SHIMOTO; M. ITO; J. YOSHIDA, CANCER CHEMOTHER. PHARMACOL., vol. 61, 2008, pages 653 - 659
G. VAIDYANATHAN; D. J. AFFLECK; C. M. CAVAZOS; S. P. JOHNSON; S. SHANKAR; H. S. FRIEDMAN; M. O. COLVIN; M. R. ZALUTSKY, BIOAONJUGATE CHEM, vol. 11, 2000, pages 868 - 875
X. LIU; Q.-H. ZHENG; X, FEI; J.-Q. WANG; D. W. OHANNESIAN; L. C. ERICKSON; K. L. STONE; G. D. HUTCHINS, BIOORG. MED. CHEM. LETT., vol. 13, 2003, pages 641 - 644
A. KEPPLER; S. GENDREIZING; T. GRONEMEYER; H. PICK; H. VOGEL; K. JOHNSSON, NATURE BIOL, vol. 21, 2003, pages 86 - 89
X. LIU; Q.-H. ZHENG; G. D. HUTCHINS; X. FEI; L. C. ERICKSON; K. D. MILLER; B. H. MOCK; B. E. GLICK-WILSOB; W. L. WINKEL; K. L. STO, SYNTH. COMMUN., vol. 33, 2003, pages 941 - 952
See also references of EP 3483160A4
SUZUKI,M. ET AL.: "Efficient synthesis of [11C]H- 1152, a PET probe specific for Rho-kinases, highly potential targets in diagnostic medicine and drug development", TETRAHEDRON, vol. 68, no. 10, 2012, pages 2336 - 2341, XP028455631
PAULY,G.T. ET AL.: "Substitution of Aminomethyl at the Meta-Position Enhances the Inactivation of O6-Alkylguanine-DNA Alkyltransferase by 06- Benzylguanine", JOURNAL OF MEDICINAL CHEMISTRY, vol. 51, no. 22, 2008, pages 7144 - 7153, XP055563122
KOYAMA,H . ET AL.: "Synthesis of PET probe O6-[(3- [11C]methyl)benzyl]guanine by Pd°-mediated rapid C-[11C]methylation toward imaging DNA repair protein O6-methylguanine-DNA methyltransferase in glioblastoma", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 27, no. 9, 18 March 2017 (2017-03-18), pages 1892 - 1896, XP029968180
A. NATSUME; D. ISHII; T. WAKABAYASI; T. TSUNO; H. HATANO; M. MIZUNO; J. YASHIDA, CANCER RES., vol. 65, 2005, pages 7573 - 7579
A. NATSUME; T. WAKABAYASHI; D. ISHII; H. MARUTA; M. FUJII; S. SHIMOTO; M. ITO; J. YOSHIDA, CANCER CHEMOTHER. PHARMACOL., vol. 61, 2008, pages 653 - 659
G. VAIDYANATHAN; D. J. AFFLECK; C. M. CAVAZOS; S. P. JOHNSON; S. SHANKAR; H. S. FRIEDMAN; M. O. COLVIN; M. R. ZALUTSKY, BIOAONJUGATE CHEM, vol. 11, 2000, pages 868 - 875
X. LIU; Q.-H. ZHENG; X, FEI; J.-Q. WANG; D. W. OHANNESIAN; L. C. ERICKSON; K. L. STONE; G. D. HUTCHINS, BIOORG. MED. CHEM. LETT., vol. 13, 2003, pages 641 - 644
A. KEPPLER; S. GENDREIZING; T. GRONEMEYER; H. PICK; H. VOGEL; K. JOHNSSON, NATURE BIOL, vol. 21, 2003, pages 86 - 89
X. LIU; Q.-H. ZHENG; G. D. HUTCHINS; X. FEI; L. C. ERICKSON; K. D. MILLER; B. H. MOCK; B. E. GLICK-WILSOB; W. L. WINKEL; K. L. STO, SYNTH. COMMUN., vol. 33, 2003, pages 941 - 952
See also references of EP 3483160A4
Attorney, Agent or Firm:
AOYAMA Yo (JP)
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