Osaka Prefecture University Public Corporation

Stella Pharma Corporation

Stella Pharma Corporation; Osaka Prefecture University Public Corporation

University Public Corporation Osaka

Yoichiro Ohta

Hideki Nakashima

Mitsunori Kirihata

Kohki Uehara

Hiroshi Takenaka

Yusuke Taguchi

Sayuri Ueda

Yuko Ishino

Tomohiro Yoshikawa

The present invention involves preparing compounds represented by the following formula: from a compound of the following formula:  In these formulae: Rrepresents a Br group, an iodine group, a Cl group, an NOgroup, or an NHgroup; Rrepresents a halogen group, an NOgroup, an NHgroup, Sn(R), N&#x2550;N&#x2014;NRR, OSOR, N RR, phenyliodonium, a heterocyclic group iodine, boric acid, or a borate ester; Rrepresents a protective group PG; Ror Rrepresent hydrogen, a protective group PG, or CH(CH)C&#x2550;N, in which NRRare together.

Production method for 2-fluoro-4-borono-L-phenylalanine, and precursor of 2-fluoro-4-borono-L-phenylalanine

The present invention involves preparing compounds represented by the formula. (In the formula: Rrepresents a Br group, an iodine group, a Cl group, an NOgroup, or an NHgroup; Rrepresents a halogen group, an NOgroup, an NHgroup, Sn(R), N&#x2550;N&#x2014;NRR, OSOR, NRR, phenyliodonium, a heterocyclic group iodine, boric acid, or a borate ester; Rrepresents a protective group PG; Ror Rrepresent hydrogen, a protective group PG, or CH(CH)C&#x2550;N, wherein NRRare together.)

F-labeled 4-boronophenylalanine (BPA) can be produced by preparing and further processing a precursor ofF-labeled BPA represented by the following formula: in which Rrepresents a bromo group, an iodo group, a fluoro group, a diazaborinane derivative, BX3or BX3M(wherein X represents a halogen atom; and Mrepresents a monovalent monoatomic cation, a polyatomic cation or a complex cation).

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

Provided are: a novel chiral 4-boronophenylalanine (BPA) derivative; a method for producing the derivative; and a method for producingF-2-fluoro-4-borono-L-phenylalanine (F-labeled BPA; 18F-BPA) using the derivative. A compound represented by formula (1) is prepared. In the formula, R represents BRR, BXor BXM(wherein X represents a halogen atom, and Mrepresents a monovalent monoatomic cation, a polyatomic cation or a complex cation); Rrepresents a hydrogen atom or a protecting group PG1; Rrepresents a hydrogen atom or a protecting group PG2; Rand Rindependently represent OH, or R, Rand B together form a ring that serves as a protecting group; and Y represents a halogen atom, NO, NH, Sn(R), N&#x2550;N&#x2014;NRR, OSOR, NRR, a substituted or unsubstituted phenyliodo group or a substituted or unsubstituted heterocyclic iodo group. The compound is reacted with a fluorination reagent to prepareF-labeled BPA.

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Osaka, Japan

Yoichiro Ohta