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 [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:wherein n is an integer of 0 or of 1 to 4; R1 is an ethyl, 1-propyl or isopropyl substituent; X is a halogen substituent or a group represented by —OR2; R2 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 R3 is a protective group.

1 . A precursor compound for radioactive halogen-labeled organic compounds, which is represented by the following formula (1): 
       
         
           
           
               
               
           
         
         wherein n is 0; 
         R 1  is an isopropyl substituent; 
         X is  18 F; and 
         R 3  is a t-butoxycarbonyl group, 
         wherein the precursor compound substantially does not give methanol in the production of 1-amino-3-[ 18 F]fluorocyclobutanecarboxylic acid from the precursor compound. 
       
     
     
         2 . (canceled) 
     
     
         3 . (canceled) 
     
     
         4 . (canceled) 
     
     
         5 . (canceled) 
     
     
         6 . (canceled) 
     
     
         7 . A diagnostic agent containing 1-amino-3-[ 18 F]fluorocyclobutanecarboxylic acid, wherein said 1-amino-3-[ 18 F]fluorocyclobutanecarboxylic acid is obtained using a precursor compound according to  claim 1 . 
     
     
         8 . A method of using 1-amino-3[ 18 F]fluorocyclobutanecarboxylic acid, the method comprising:
 producing 1-amino-3-[ 18 F]fluorocyclobutanecarboxylic acid from a precursor compound according to  claim 1 ;   deprotecting the precursor compound to produce 1-amino-3-[ 18 F]fluorocyclobutanecarboxylic acid, wherein the deprotection produces isopropanol;   and subsequently administering the 1-amino-3-[ 18 F]fluorocyclobutanecarboxylic acid to a subject and carrying out Positron Emission Tomography.   
     
     
         9 . A method of diagnosing tumors using Positron Emission Tomography, the method comprising:
 producing 1-amino-3-[ 18 F]fluorocyclobutanecarboxylic acid from a precursor compound according to  claim 1 ;   deprotecting the precursor compound to produce 1-amino-3-[ 18 F]fluorocyclobutanecarboxylic acid, wherein the deprotection produces isopropanol;   and subsequently administering the 1-amino-3-[ 18 F]fluorocyclobutanecarboxylic acid to a subject and carrying out Positron Emission Tomography.   
     
     
         10 . The method according to  claim 9 , wherein the method substantially does not give methanol in the production of 1-amino-3-[ 18 F]fluorocyclobutanecarboxylic acid from the precursor compound. 
     
     
         11 . The method according to  claim 8 , wherein the deprotection comprises a method in which acid is added. 
     
     
         12 . The method according to  claim 11 , wherein the acid is hydrochloric acid. 
     
     
         13 . A method for the production of 1-amino-3-[ 18 F]fluorocyclobutanecarboxylic acid from a precursor compound according to  claim 1 , 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-[ 18 F]fluorocyclobutanecarboxylic acid, wherein the deprotecting comprises a method in which acid is added,   and wherein the method substantially does not give methanol in the production of 1-amino-3-[ 18 F]fluorocyclobutanecarboxylic acid from the precursor compound.   
     
     
         14 . The method according to  claim 13 , wherein the acid is hydrochloric acid. 
     
     
         15 . A method of using 1-amino-3[ 18 F]fluorocyclobutanecarboxylic acid, the method comprising:
 administering the 1-amino-3-[ 18 F]fluorocyclobutanecarboxylic acid to a subject; and carrying out Positron Emission Tomography;   wherein the 1-amino-3-[ 18 F]fluorocyclobutanecarboxylic acid is produced from a precursor compound according to  claim 1 .