Method for producing 4-borono-l-phenylalanine having 18f atom introduced thereinto, and precursor of 4-borono-l-phenylalanine having 18f atom introduced thereinto

Patent metadata

Field	Value
Publication number	US-2017015684-A1
Application number	US-201515122118-A
Country	US
Kind code	A1
Filing date	Jan 28, 2015
Priority date	Feb 28, 2014
Publication date	Jan 19, 2017
Grant date	—

Abstract

18 F-labeled 4-boronophenylalanine (BPA) can be produced by preparing and further processing a precursor of 18 F-labeled BPA represented by the following formula:

in which R 1 represents a bromo group, an iodo group, a fluoro group, a diazaborinane derivative, BX3 − or BX3 − M + (wherein X represents a halogen atom; and M + represents a monovalent monoatomic cation, a polyatomic cation or a complex cation).

First claim

1 . A compound represented by a formula below:

wherein R 1 represents bromo group, iodo group, fluoro group, a diazaborinane derivative, BX 3 − , or BX 3 − M + (X represents halogen, and M + represents monovalent monoatomic cation, polyatomic cation, or complex cation).

2 . The compound according to claim 1 , wherein X represents F, and M + represents an alkali metal ion, an ammonium ion, a tetraalkylammonium ion, a tetraarylammonium ion, a tetraalkylphosphonium ion, a tetraarylphosphonium ion, or an imidazolium ion.

3 . A method for producing a compound represented by a formula below:

where R 1 represents bromo group, iodo group, fluoro group, a diazaborinane derivative, BX 3 − , or BX 3 − M + (X represents halogen, and M + represents monovalent monoatomic cation, polyatomic cation, or complex cation), comprising:
using a compound represented by a formula below:

where R 1 represents bromo group, iodo group, fluoro group, a diazaborinane derivative, BX 3 − , or BX 3 − M + (X represents halogen, and M + represents monovalent monoatomic cation, polyatomic cation, or complex cation), and R 2 represents any one selected from the group consisting of halogen, amino group, nitro group, boronic acid, boronic acid ester, OSO 2 R 3 , NR 4 R 5 , and N + R 4 R 5 R 6 R 7 (where R 3 represents alkyl group having 1 to 7 carbon atoms, halogen-substituted alkyl group having 1 to 7 carbon atoms, or optionally substituted phenyl group; R 4 and R 5 , which are the same or different, each represent alkyl group having 1 to 7 carbon atoms, halogen-substituted alkyl group having 1 to 7 carbon atoms, or optionally substituted phenyl group, or R 4 and R 5 are combined together with N to form a 3- to 7-membered cyclic structure; R 6 represents alkyl group having 1 to 7 carbon atoms; and R 7 represents halogen or sulfonate).

4 . A method for producing 18 F-labeled 4-boronophen dalanine BPA, comprising:
using a compound represented by a formula below:

where R 1 represents bromo group, iodo group, fluoro group, chloro group, nitro group, amino group, a diazaborinane derivative, BX 3 − , or BX 3 − M + (X represents halogen, and M + represents monovalent monoatomic cation, polyatomic cation, or complex cation).

5 . The method for producing 18 F-labeled BPA according to claim 4 , wherein X represents F, and M + represents an alkali metal ion, an ammonium ion, a tetraalkylammonium ion, a tetraarylammonium ion, a tetraalkylphosphonium ion, a tetraarylphosphonium ion, or an imidazolium ion.

Assignees

• Stella Pharma Corp
• Univ Osaka Prefect Public Corp

Inventors

• Takenaka Hiroshi
• Ohta Yoichiro
• Taguchi Yusuke
• Ueda Sayuri
• Ishino Yuko
• Yoshikawa Tomohiro
• Nakashima Hideki
• Uehara Kohki
• Kirihata Mitsunori

Classifications

• C07C45/63

  by introduction of halogen; by substitution of halogen atoms by other halogen atoms · CPC title

• C07F5/025 Primary

  Boronic and borinic acid compounds · CPC title

• C07B59/00

  Introduction of isotopes of elements into organic compounds {; Labelled organic compounds per se} · CPC title

• C07C47/55

  containing halogen · CPC title

• C07B59/004

  Acyclic, carbocyclic or heterocyclic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur, selenium or tellurium · CPC title