Details for Patent: 9,381,259

Title:	Precursor compound of radioactive halogen-labeled organic compound
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 [.sup.18F]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: ##STR00001## wherein n is an integer of 0 or of 1 to 4; R.sup.1 is an ethyl, 1-propyl or isopropyl substituent; X is a halogen substituent or a group represented by --OR.sup.2; R.sup.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.sup.3 is a protective group.
Inventor(s):	Ito; Osamu (Chiba, JP), Hayashi; Akio (Chiba, JP), Kurosaki; Fumie (Chiba, JP), Toyama; Masahito (Chiba, JP), Shinmura; Toshiyuki (Chiba, JP), Harano; Arinori (Chiba, JP)
Assignee:	NIHON MEDI-PHYSICS CO., LTD. (Tokyo, JP)
Filing Date:	Apr 07, 2014
Application Number:	14/246,594
Claims:	1. A method for the production of 1-amino-3-[.sup.18F]fluorocyclobutanecarboxylic acid from a precursor compound which is represented by the following formula (1 ): ##STR00003## wherein n is 0, R.sup.1 is an ethyl substituent, X is a trifluoromethanesulfonate substituent and R.sup.3 is a t-butoxycarbonyl substituent, wherein the method includes adding radioactive fluoride to the precursor compound, wherein the reaction with radioactive fluoride is carried out in acetonitrile, and deprotecting the precursor compound to which radioactive fluoride has been added to produce 1-amino-3-[.sup.18F]fluorocyclobutanecarboxylic acid, wherein the deprotecting comprises a method in which an acid is added, wherein the method substantially does not give methanol in the production of 1-amino-3-[.sup.18]fluorocyclobutanecarboxylic acid from the precursor compound. 2. The method according to claim 1, wherein the acid is hydrochloric acid. 3. A method for the production of 1-amino-3-[.sup.18F]fluorocyclobutanecarboxylic acid from a precursor compound which is represented by the following formula (2) ##STR00004## wherein formula (2) TfO represents a trifluoromethanesulfonate substituent, BOC represents a t-butoxy carbonyl substituent, and Et represents an ethyl substituent, wherein said method includes the addition of radioactive fluoride to the precursor compound, wherein the addition is carried out in acetonitrile; and deprotecting the precursor compound to which radioactive fluoride has been added to produce 1-amino-3-[.sup.18F]fluorocyclobutanecarboxylic acid, wherein the deprotecting comprises a method in which an acid is added, and wherein the method substantially does not give methanol in the production of 1-amino-3-[.sup.18F]fluorocyclobutanecarboxylic acid from the precursor compound. 4. A method for the production of 1-amino-3-[.sup.18F]fluorocyclobutanecarboxylic acid from a precursor compound which is represented by the following formula (2) ##STR00005## wherein formula (2) TfO represents a trifluoromethanesulfonate substituent, BOC represents a t-butoxy carbonyl substituent, and Et represents an ethyl substituent, wherein said method includes the addition of radioactive fluoride to the precursor compound, wherein the addition is carried out in acetonitrile; and deprotecting the precursor compound to which radioactive fluoride has been added to produce 1-amino-3-[.sup.18F]fluorocyclobutanecarboxylic acid, wherein the deprotecting comprises a method in which hydrochloric acid acid is added, and wherein the method substantially does not give methanol in the production of 1-amino-3-[.sup.18F]fluorocyclobutanecarboxylic acid from the precursor compound.