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Catalytic radiofluorination

A technology of radioactivity and compounds, applied in the direction of radioactive carriers, radioactive preparations in vivo, organic chemical methods, etc.

Inactive Publication Date: 2007-02-28
THE GENERAL HOSPITAL CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, many bioactive molecules, drugs, receptor ligands, peptides, and proteins are difficult to use in clinical nuclear medicine because of limitations inherent in the methods used to implant F-18

Method used

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  • Catalytic radiofluorination
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preparation example Construction

[0039] Another aspect of the present invention relates to a method for the preparation of aryl halides by reacting triazine with sodium iodide and chlorotrimethylsilane to prepare aryl halides. In a preferred embodiment, the iodine is radioactive iodine. In some embodiments, iodine is 123 I. 124 I. 125 I or 131 I. In a preferred embodiment, iodine is 125 I. The reaction can be carried out in the presence or absence of a solvent. For reactions performed in the presence of a solvent, the reaction will be suitable for most organic solvents that do not contain hydroxyl groups that can react with the reaction substrates. Representative selections of suitable solvents include acetonitrile, dimethylacetamide, dimethylformamide, dimethylsulfoxide, dioxane, benzene, toluene, xylene, ethylbenzene, diglyme, dimethoxy Diethylene glycol dimethyl ether (ethylene glycol dimethyl ether), diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, tetraethylene glycol dimethyl ...

Embodiment 1

[0621] Synthesis of [F-18]-1-methyl-1-(4-fluorophenyl)piperazinium salt

[0622]

[0623] Heating t-BOC-protected methylpiperazine under pressure in benzene in the presence of 1-fluoro-4-nitrobenzene gave 4-t-BOC-protected 1-methyl-1-( 4-nitrophenyl)piperazinium salt. The resulting piperazinium salt was heated at 200°C for 10 minutes in the presence of [18F]potassium fluoride and Krytofix. The resulting oil was treated with 3M aqueous HCl for 20 minutes to afford [F-18]-1-methyl-1-(4-fluorophenyl)piperazinium chloride.

Embodiment 2

[0625] Synthesis of [F-18]-1-(4-fluorocyclohexyl)-1-methyl-4-phenylpiperazinium iodide

[0626]

[0627] A solution of 1,4-cyclohexanediol (cis / trans mixture, 10 g, 86 mmol), benzoyl chloride (12 g, 86 mmol) and DMAP (50 mg) in dichloromethane / pyridine (80 / 20) was stirred at 25 °C for 4 Hour. The resulting reaction mixture was washed with 10% HCl until the aqueous layer was acidified, and the dichloromethane layer was washed with saturated NaHCO 3 , washed with brine, dried (Na 2 SO 4 ). After removal of the solvent, the crude product was chromatographed (silica gel, dichloromethane / methanol, 95:5) to yield 6 g (30%) of benzoyl alcohol.

[0628] 4-Benzoylcyclohexanol (5 g, 23 mmol) was oxidized with PCC (7.4 g, 34.5 mmol) in dichloromethane (50 mL) for 2 hours at 25°C. The black reaction mixture was filtered through a short bed of silica gel and the solvent was removed. Purification by chromatography (silica gel, hexane / ethyl acetate, 85:15) afforded 3 g (60%) of the ...

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Abstract

One aspect of the invention relates to methods for the preparation of radioactively fluorinated substituted alkyl, cycloalkyl, aryl and alkenyl compounds. In a preferred embodiment, use 18 Potassium fluoride. Another aspect of the invention relates to fluorine-18-containing piperazine compounds for use as contrast agents. In certain embodiments, the piperazine compound contains quaternary ammonium. Another aspect of the invention relates to fluorine-18-containing arylphosphonium compounds for use as contrast agents. In certain embodiments, the phosphonium compound is a tetraarylphosphonium salt. Another aspect of the invention relates to a method of obtaining a positron emission image of a mammal, the method comprising administering a compound of the invention to the mammal and obtaining a positron emission spectrum of the mammal.

Description

[0001] related application [0002] This application claims the benefit of priority to US Provisional Patent Application Serial No. 60 / 547,206, filed February 24, 2004; the entire disclosure of said Provisional Application is incorporated herein by reference. Background of the invention [0003] Modern medical imaging relies heavily on the use of radioisotopes. One of the earliest radioisotopes used clinically was technetium (Tc). The element was originally identified as Na in 1961 99m TCO 4 form given to patients. Other radioisotopes have also been developed as potential contrast agents, including halogens (e.g. 125 I. 131 I and 82 Br) and isotopes of various metallic radionuclides of lead, gallium, rhenium, arsenic and copper. Medical imaging has a variety of medical uses, including imaging of the brain, tumors, and parts of the cardiovascular system. [0004] Blood flow contrast agents are currently the most important tool for...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K51/00A61K51/04C07D241/04
CPCC07B2200/05A61K51/04C07B59/00A61B6/508A61B6/507C07D241/04
Inventor D·埃尔马勒T·M·索普A·J·费希曼
Owner THE GENERAL HOSPITAL CORP
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