Stella Pharma Corporation

Osaka Prefecture University Public Corporation

Japan Science and Technology Agency

Stella Chemifa Corporation

Osaka Prefecture University

Stella Pharma Corporation; Osaka Prefecture University Public Corporation

University Public Corporation Osaka

Kohki Uehara

Mitsunori Kirihata

Hiroshi Takenaka

Hideki Nakashima

Yoichiro Ohta

Yusuke Taguchi

Sayuri Ueda

Yuko Ishino

Tomohiro Yoshikawa

Yoshihide Hattori

Tomoyuki Asano

Shintaro Kusaka

To provide a novel boron-containing compound. A compound represented by the following formula: wherein black circle represents B, white circles represent B&#x2014;H; &#x2014;Rrepresents &#x2014;(CH)n-X&#x2014;R(n represents an integer of 0 to 6; Xrepresents O, S, NH, S&#x2014;S, O&#x2014;CO, NHCO or SCO, or does not exist; Rrepresents C-Calkyl, hydroxy C-Calkyl, amino C-Calkyl, azido C-Calkyl, hydroxycarbonyl C-Calkyl, or the like), or a group having a repeating sequence of &#x2014;(CH)&#x2014;O&#x2014; 3 times or more and 10 times or less and having a methyl group or an ethyl group at the end on the oxygen atom side; and &#x2014;Ris &#x2014;(CH)m-X&#x2014;R(m represents an integer from 0 to 8; Xrepresents O, S, NH, S&#x2014;S, O&#x2014;CO, NHCO or SCO, or does not exist; and Rrepresents a tumor recognition moiety), or does not exist are prepared and used. 

Boron-containing compound

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

The purpose of the present invention is to provide a novel method for producing cereulide and a derivative thereof; an intermediate for cereulide; and a novel cereulide derivative. A novel didepsipeptide, a novel tetradepsipeptide, a novel octadepsipeptide and a novel dodecadepsipeptide are prepared. A linear precursor of cereulide or a derivative thereof, which is composed of any one of the novel depsipeptides, is cyclized by forming an intramolecular amide bond.

Method for producing cereulide and derivative thereof, intermediate for production of cereulide, and cereulide derivative

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.

[object Object]

The purpose of the present invention is to provide a novel boron-containing compound utilizable in BNCT and so on and a process for preparing same. According to the process, a boron compounds having an amino acid skeleton containing cyclo-type rings or a pharmaceutically acceptable salt thereof is prepared, said boron compound being represented by general formula (I) [wherein l is an integer of 1 to 6; m is 0, 1, or 2; and n is 0, 1 or 2]. 

Boron compound with amino acid skeleton containing cyclo ring-type ring

The present invention is a compound having a structure represented by the following formula (1): and an antibody to BSH obtained by using the compound as a hapten and using a complex of the hapten and a high-molecular compound as an antigen. By using the present invention, it becomes possible to provide a hapten compound for preparing an antibody recognizing BSH highly sensitively and highly selectively, an antibody to BSH, as well as a kit for measuring BSH and an immunological measuring method having high sensitivity and excellent in quantitative property using the antibody.

Hapten compound and antibody

Disclosed is the method for producing an optically active BSH amino acid, which comprises a step of reacting an optically active a-amino acid derivative having a halogen in a side chain with a cyanoethyl BSH compound represented by formula (1). An optically active BSH amino acid obtained by the method is also disclosed. 

Growing community of inventors

Osaka, Japan

Kohki Uehara