Title:
CHIRAL 4-BORONOPHENYLALANINE (BPA) DERIVATIVE AND METHOD FOR PRODUCING SAME, AND METHOD FOR PRODUCING 18F-LABELED BPA USING SAID DERIVATIVE
Document Type and Number:
WIPO Patent Application WO/2014/061508
Kind Code:
A1
Abstract:
Provided are: a novel chiral 4-boronophenylalanine (BPA) derivative; a method for producing the derivative; and a method for producing 18F-2-fluoro-4-borono-L-phenylalanine (18F-labeled BPA; 18F-BPA) using the derivative.
A compound represented by formula (1) is prepared.
In the formula, R represents BR3R4, BX3
- or BX3
-M+ (wherein X represents a halogen atom, and M+ represents a monovalent monoatomic cation, a polyatomic cation or a complex cation); R1 represents a hydrogen atom or a protecting group PG1; R2 represents a hydrogen atom or a protecting group PG2; R3 and R4 independently represent OH, or R3, R4 and B together form a ring that serves as a protecting group; and Y represents a halogen atom, NO2, NH2, Sn(R6)3, N=N-NR7R8, OSO2R9, NR10R11, a substituted or unsubstituted phenyliodo group or a substituted or unsubstituted heterocyclic iodo group (wherein R6 represents an alkyl group having 1 to 7 carbon atoms, R7 and R8 may be the same as or different from each other, and independently represent a hydrogen atom, an alkyl group having 1 to 7 carbon atoms, an alkyl group having 1 to 7 carbon atoms which is substituted by a halogen atom or an optionally substituted phenyl group or R7, R8 and N together form a 3- to 7-membered cyclic structure, R9 represents an alkyl group having 1 to 7 carbon atoms, an alkyl group having 1 to 7 carbon atoms which is substituted by a halogen atom, or an optionally substituted phenyl group, and R10 and R11 may be the same as or different from each other, and independently represent an alkyl group having 1 to 7 carbon atoms, an alkyl group having 1 to 7 carbon atoms which is substituted by a halogen atom, or an optionally substituted phenyl group or R10, R11 and N together form a 3- to 7-membered cyclic structure, wherein when Y is F, a case in which each of R1 and R2 represents a hydrogen atom and each of R3 and R4 represents OH is excluded). The compound is reacted with a fluorination reagent to prepare 18F-labeled BPA.
Inventors:
TAKENAKA HIROSHI (JP)
OHTA YOICHIRO (JP)
TAGUCHI YUSUKE (JP)
UEDA SAYURI (JP)
ISHINO YUKO (JP)
NAKASHIMA HIDEKI (JP)
UEHARA KOHKI (JP)
KIRIHATA MITSUNORI (JP)
OHTA YOICHIRO (JP)
TAGUCHI YUSUKE (JP)
UEDA SAYURI (JP)
ISHINO YUKO (JP)
NAKASHIMA HIDEKI (JP)
UEHARA KOHKI (JP)
KIRIHATA MITSUNORI (JP)
Application Number:
PCT/JP2013/077366
Publication Date:
April 24, 2014
Filing Date:
October 08, 2013
Export Citation:
Assignee:
STELLA PHARMA CORP (JP)
UNIV OSAKA PREFECT PUBLIC CORP (JP)
UNIV OSAKA PREFECT PUBLIC CORP (JP)
International Classes:
C07F5/04; C07C229/36; C07F7/22; C07B59/00
Foreign References:
| JP2008214319A | 2008-09-18 | |||
| JP2000212185A | 2000-08-02 |
Other References:
MEYER, FALCO-MAGNUS ET AL.: "Functionalization of aromatic amino acids via direct C-H activation: generation of versatile building blocks for accessing novel peptide space", ORGANIC LETTERS, vol. 12, no. 17, 2010, pages 3870 - 3873, XP055030972
PORCARI, P. ET AL.: "In vivo 19F MR imaging and spectroscopy for the BNCT optimization", APPLIED RADIATION AND ISOTOPES, vol. 67, no. 7-8S, 2009, pages S365 - S368, XP026195996
TUTTLE, JAMISON B. ET AL.: "Synthesis of ortho- substituted nitroaromatics via improved Negishi coupling conditions", TETRAHEDRON LETTERS, vol. 52, no. 41, 2011, pages 5211 - 5213, XP028286434
MCALLISTER, LAURA A. ET AL.: "A General Strategy for the Synthesis of Cyclic N-Aryl Hydroxamic Acids via Partial Nitro Group Reduction", JOURNAL OF ORGANIC CHEMISTRY, vol. 76, no. 9, 2011, pages 3484 - 3497, XP002711410
ENDO, YASUYUKI ET AL.: "Role of the hydrophobic moiety of tumor promoters. Synthesis and activity of 9-alkylated benzolactams", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 44, no. 5, 1996, pages 1138 - 1140, XP055247210
See also references of EP 2907818A4
APPL. RADIAT. ISOT., vol. 42, 1991, pages 325
J. LABEL. COMPD. RADIOPHARM., vol. 45, 2002, pages 697
GREENE WUTS: "Protective Groups in Organic Synthesis", WILEY-INTERSCIENCE
SCIENCE, vol. 325, 2009, pages 1661
J. LABEL. COMPD. RADIOPHARM., vol. 47, 2004, pages 429
PORCARI, P. ET AL.: "In vivo 19F MR imaging and spectroscopy for the BNCT optimization", APPLIED RADIATION AND ISOTOPES, vol. 67, no. 7-8S, 2009, pages S365 - S368, XP026195996
TUTTLE, JAMISON B. ET AL.: "Synthesis of ortho- substituted nitroaromatics via improved Negishi coupling conditions", TETRAHEDRON LETTERS, vol. 52, no. 41, 2011, pages 5211 - 5213, XP028286434
MCALLISTER, LAURA A. ET AL.: "A General Strategy for the Synthesis of Cyclic N-Aryl Hydroxamic Acids via Partial Nitro Group Reduction", JOURNAL OF ORGANIC CHEMISTRY, vol. 76, no. 9, 2011, pages 3484 - 3497, XP002711410
ENDO, YASUYUKI ET AL.: "Role of the hydrophobic moiety of tumor promoters. Synthesis and activity of 9-alkylated benzolactams", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 44, no. 5, 1996, pages 1138 - 1140, XP055247210
See also references of EP 2907818A4
APPL. RADIAT. ISOT., vol. 42, 1991, pages 325
J. LABEL. COMPD. RADIOPHARM., vol. 45, 2002, pages 697
GREENE WUTS: "Protective Groups in Organic Synthesis", WILEY-INTERSCIENCE
SCIENCE, vol. 325, 2009, pages 1661
J. LABEL. COMPD. RADIOPHARM., vol. 47, 2004, pages 429
Attorney, Agent or Firm:
UNIUS PATENT ATTORNEYS OFFICE (JP)
Patent business corporation ユニアス international patent firm (JP)
Patent business corporation ユニアス international patent firm (JP)
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