Novel Reaction Scheme for Synthesis of PET Markers

Higher yields and purity than current methods Lower costs Efficient and convenient Broader than PET tracing; can be applied to other fields (i.e. diagnostics, pharmacology, etc)

The basic synthesis method includes a “no-carrier-added” [F-18] fluoride ion reacting with an iodylbenzene derivative, with the fluoride ion nucleophilically substituting the iodyl group (IO2) on the aromatic ring, resulting in regiospecific F-18 labeled aromatic compounds.  In the above reaction “a” is either NaOCl or dimethyldioxirane and “b” is a source of no-carrier-added 18F. A large number of iodylbenzene derivative have been reacted using this procedure to produce F-18 labeled aryl analogs. The [F-18] fluoride ion regiospecifically substitutes the iodyl group on the aromatic ring. For example, the PET marker 6-[F-18]-fluoro-L-dopa has been synthesized utilizing this reaction scheme.

Patent Number: US20110178302A1
Application Number: US13054458A
Inventor: Satyamurthy, Nagichettiar | Barrio, Jorge R.
Priority Date: 14 Jul 2008
Priority Number: US20110178302A1
Application Date: 1 Apr 2011
Publication Date: 21 Jul 2011
IPC Current: C07D024108 | C07C001720 | C07C004563 | C07C0067307 | C07C020112 | C07C022716 | C07C025330 | C07D021361 | C07D023332 | C07D026318 | C07D027766
US Class: 544408 | 546345 | 548178 | 548228 | 5483164 | 558425 | 560035 | 560103 | 568316 | 568433 | 568937 | 570142
Assignee Applicant: The Regents of the University of California
Title: NUCLEOPHILIC FLUORINATION OF AROMATIC COMPOUNDS
Usefulness: NUCLEOPHILIC FLUORINATION OF AROMATIC COMPOUNDS
Summary: For preparing compounds labeled with a radiation emitting halogen groups e.g. [F-18] fluorinated labeled compounds (claimed) useful as biomarkers in positron emission tomography (PET).
Novelty: Preparing compounds labeled with radiation emitting halogen groups useful as biomarkers involves replacing halogen of benzene derivative containing pendent halogen, by isotopic ion of halogen to produce halogen labeled benzene derivative

Chemical/Material

Organic Chemical

8674101

State Of Development

We continue to demonstrate the broad range of molecules capable of synthesis with thismethod.

Background

Incorporating positron emitting fluorine-18 into aromatic ring systems plays a very important role in the development of novel biomarkers for use in Positron Emission Tomography (PET). Current methods of preparing biomarkers include nucleophilic fluorine substitution reactions, however the yield obtained by this reaction drops drastically as the complexity of the aromatic ring system increases. UCLA researchers have developed a novel nucleophilic fluorination reaction of aromatic compounds with a no-carrier-added [F-18] fluoride ion. This reaction is suitable for the preparation of F-18 labeled biomarkers containing a variety of substituents and allows for the synthesis of biomarkers and molecular imaging probes for PET with higher yields and purity than currently used methods. The reaction can be expanded to a multitude of labeled and unlabeled molecules.

Tech ID/UC Case

23208/2008-664-0

Related Cases

2008-664-0

USA

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