Precursor compound of radioactive halogen-labeled organic compound

Patent metadata

Field	Value
Publication number	US-10010632-B2
Application number	US-201514872305-A
Country	US
Kind code	B2
Filing date	Oct 1, 2015
Priority date	Nov 29, 2005
Publication date	Jul 3, 2018
Grant date	Jul 3, 2018

Abstract

It is intended to provide a novel amino acid organic compound which can be used as a labeling precursor compound for radioactive halogen-labeled amino acid compounds including [ 18 F]FACBC, and which prevents methanol from remaining in the radioactive halogen-labeled amino acid compounds produced therefrom. The novel amino acid organic compound is a compound represented by the following formula:

wherein n is an integer of 0 or of 1 to 4; R 1 is an ethyl, 1-propyl or isopropyl substituent; X is a halogen substituent or a group represented by —OR 2 ; R 2 is a straight-chain or branched-chain haloalkylsulfonic acid substituent with one to 10 carbon atoms, trialkylstannyl substituent with 3 to 12 carbon atoms, fluorosulfonic acid substituent or aromatic sulfonic acid substituent; and R 3 is a protective group.

First claim

The invention claimed is:

1. A diagnostic agent containing 1-amino-3-[ 18 F]fluorocyclobutanecarboxylic acid and ethanol rather than methanol as an impurity, wherein said 1-amino-3-[ 18 F]fluorocyclobutanecarboxylic acid is obtained using a precursor compound that substantially gives ethanol rather than methanol in the production of 1-amino-3-[ 18 F]fluorocyclobutanecarboxylic acid, wherein said precursor compound is represented by the following formula (1):

wherein n is 0; R 1 is an ethyl substitutent; X is a trifluoromethanesulfonic acid substitutent;
and R 3 is a t-butoxycarbonyl group.

2. The diagnostic agent according to claim 1 , wherein the precursor compound is represented by formula (2):

wherein Et is an ethyl substitutent; TfO is a trifluoromethanesulfonic acid substitutent; and
Boc is a t-butoxycarbonyl group.

Assignees

• Nihon Mediphysics Co Ltd

Inventors

• Ito Osamu
• Hayashi Akio
• Kurosaki Fumie
• Toyama Masahito
• Shinmura Toshiyuki
• Harano Arinori

Classifications

• C07B2200/05

  Isotopically modified compounds, e.g. labelled · CPC title

• C07C67/307

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

• C07C2601/04

  with a four-membered ring · CPC title

• C07C309/65 Primary

  of a saturated carbon skeleton · CPC title

• A61K51/0406 Primary

  Amines, polyamines, e.g. spermine, spermidine, amino acids, (bis)guanidines · CPC title