Princeton Docket # 12-2797/2758-1
Chemists in the laboratory of Professor John T Groves, Princeton University have discovered a powerful, simple and potentially disruptive technology for drug diversification through direct fluorination (3D-F). Fluorine is a highly desirable drug component because replacement of hydrogen with fluorine usually results in higher potency, better pharmacology, and lower metabolic burden to the patient. As a result an increasing fraction of new drug entities, as well as agrochemical compounds, contain fluorine. Another important driver for fluorinated drugs comes from PET imaging techniques that illuminate drug distributions in the body with radioactive 18F.
Major bottlenecks for the industry derive from the difficulties chemists encounter in handling toxic, corrosive and difficult to prepare fluorinating agents. Our method involves easily handled fluoride salts and readily prepared manganese-containing catalysts. Drugs and drug-like molecules have been selectively fluorinated at otherwise inaccessible sites in a single step. A paper describing this work recently appeared in the journal Science and has been highlighted by Chemical Engineering News, Nature and the Royal Society of Chemistry. Our best catalysts are new compositions of matter that hold promise for a strong patent position, in addition to the method itself and the novel fluorinated structures that we have produced.
· Drug diversification
· Novel, small molecule generation
· Generation of biologically active molecules, and agrochemicals
· Clean, fast, and inexpensive
· One step, catalytic process using readily available fluoride salts
Liu,W., Huang, X., Cheng, MJ., Nielsen, RJ.,Goddard III, W., Groves, JT., Oxidative Aliphatic C-H Fluorination with Fluoride Ion Catalyzed by a Manganese Porphyrin, Science 14 September 2012: 1322-1325. [DOI:10.1126/science.1222327].
Chemists Score Alkyl Fluorination, Organic Synthesis: Single direct fluorination of C-H bonds adds to research hot streak, p.7, News of the Week, Chemical and Engineering News, Sept. 17, 2012.
Intellectual Property & Development Status
Two PCT applications have been filed. Princeton is seeking industrial collaborators for the further development and commercialization of this technology.
Principal Investigator and Inventor
Professor John T Groves, Professor of Chemistry
Professor Groves major thrust of research is at the interface of organic, inorganic, and biological chemistry. Many biochemical transformations as well as important synthetic and industrial processes are catalyzed by metals. Current efforts focus on the design of new, biomimetic catalysts and the molecular mechanisms of these processes, the design and assembly of large scale membrane-protein-small molecule constructs, studies of host-pathogen interactions related to iron acquisition by small molecule siderophores and molecular probes of the role of peroxynitrite in biological systems. Professor Groves is the recipient of many accolades, including recent awards of the 2010 Hans Fischer Career Award in Prophyrin Chemistry and the 2010 Remsen Award. He also was one of two people selected to receive the 2008 Grand Prix de la Fondation de la Maison de la Chimie, for his work with cytochrome P450 enzymes and model metalloporphyrin catalysts.
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