Radiofluorinated compounds and their preparation

Abstract

The present invention provides a process for [ 18 F]-fluorination of biomolecules containing a primary amino group such as proteins and peptides and in particular of peptides. The invention further provides reagents for this process, in particular 18 F-labelled prosthetic groups for use in the preparation as well as non-labelled intermediates useful in the preparation of the [ 18 F]-labelled prosthetic groups. [ 18 F]-labelled compounds useful as radiopharmaceuticals, specifically for use in Positron Emission Tomography (PET) are also provided.

What is claimed is: 
     
         1 - 26 . (canceled) 
     
     
         27 . Radiopharmaceutical composition comprising a compound of formula (7) 
       
         
           
           
               
               
           
         
       
       wherein R 1  denotes H or C 1 -C 4  alkyl, Spacer denotes a C 1 -C 4  alkylene group optionally interrupted by an oxygen atom, R 2  denotes a bio-molecule residue having at least one free amino function, and X denotes a physiological acceptable anion, optionally together with a solvent or excipient. 
     
     
         28 . Compound of formula (6) 
       
         
           
           
               
               
           
         
       
       wherein R 1  denotes H or C 1 -C 4  alkyl, Spacer denotes a C 1 -C 4  alkylene group optionally interrupted by an oxygen atom, and X denotes a physiological acceptable anion. 
     
     
         29 . Compound of formula (4) 
       
         
           
           
               
               
           
         
       
       wherein R 1  denotes H or C 1 -C 4  alkyl and Spacer denotes a C 1 -C 4  alkylene group optionally interrupted by an oxygen atom. 
     
     
         30 . Compound of formula (3): 
       
         
           
           
               
               
           
         
       
       wherein R 1  denotes H or C 1 -C 4  alkyl and Spacer denotes a C 1 -C 4  alkylene group optionally interrupted by an oxygen atom. 
     
     
         31 . Compound of formula (2): 
       
         
           
           
               
               
           
         
       
       wherein R 1  denotes H or C 1 -C 4  alkyl, Spacer denotes a C 1 -C 4  alkylene group optionally interrupted by an oxygen atom, and A denotes an amino protection group such as BOC (tert-butyl ester). 
     
     
         32 . Compound of formula (5) 
       
         
           
           
               
               
           
         
       
       wherein R 1  denotes H or C 1 -C 4  alkyl, Spacer denotes a C 1 -C 4  alkylene group optionally interrupted by an oxygen atom, or R 1  and Spacer together with the adjacent nitrogen atom forms a 4-azonia-spiro[3.5]nonyl group, and X denotes a physiological acceptable anion. 
     
     
         33 . Radiofluorination kit comprising a compound (5): 
       
         
           
           
               
               
           
         
       
       wherein R 1 , Spacer, and X have the meanings of claim  35 . 
     
     
         34 . Radiofluorination kit of claim  36  further comprising a compound of formula (8):
   R 2 NH 2   (8)
 
 
       wherein R 2  denotes a bio-molecule residue having at least one free amino function.