Technologies
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WARF: P110299US02

Easier, More Flexible Synthesis of Therapeutic and Promising Compounds


INVENTORS -

Jennifer Schomaker, Luke Boralsky, John Hershberger, Jared Rigoli, Christopher Adams

The Wisconsin Alumni Research Foundation (WARF) is seeking commercial partners interested in developing methods for preparing asymmetric, heteroatom-bearing stereotriads and tetrads via the oxidation of allene molecules.
OVERVIEWMany pharmaceuticals and other biologically active molecules contain chemical sequences called triads that are challenging to prepare in the laboratory. Specifically, triads are three or more contiguous heteroatom-bearing carbons. These sequences are featured in useful compounds like the anti-influenza medicine Tamiflu, which relies on a unique Chinese evergreen and lengthy manufacturing process. The drug’s reliance on natural sources has led to supply shortages in the past.

New methods clearly are needed for synthesizing these important sequences. A promising strategy is to explore allene molecules. Allenes are links of three double-bonded carbon atoms that could serve as building blocks for useful and promising products.
THE INVENTIONUW–Madison researchers have developed efficient processes to prepare asymmetric, heteroatom-bearing stereotriads and tetrads via allene oxidation. The number and type of heteroatoms stereoselectively introduced into the hydrocarbon chain or ring is flexible, and the methods allow for the transfer of chirality to three new carbon-heteroatom bonds. The new triads and tetrads may be incorporated into biologically active molecules, including modified aminoglycoside and neuraminidase inhibitors.

Any reaction products can be further oxidized, reduced or hydrolyzed to form other compounds and intermediates, notably synthetic motifs containing three contiguous carbon-heteroatom bonds. Bicyclic methylene aziridines can be formed and altered to provide therapeutically-promising N,N-aminals in a one pot reaction.
APPLICATIONS
  • New compounds and synthetic methods
  • Production of therapeutics
KEY BENEFITS
  • Easy preparation from readily accessible allenes
  • Ability to introduce a wide variety of functionality
  • Mild reaction conditions
  • Subsequent reactivity can be promoted.
  • Inherent ring strain in the aziridine promotes facile ring opening and high degree of possible stereocontrol.
ADDITIONAL INFORMATION
For More Information About the Inventors
Related Intellectual Property
Publications
  • Boralsky L.A., Marston D., Grigg R.D., Hershberger J.C. and Schomaker J.M. 2011. Allene Functionalization via Bicyclic Methylene Aziridines. Org. Lett. 13, 1924.
Contact Information
For current licensing status, please contact Mark Staudt at mstaudt@warf.org or 608-960-9845.
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UW–Madison has the integrative capabilities to complete many key components of the drug development cycle, from discovery through clinical trials. As one of the top research universities in the world, and one of the two best-funded universities for research in the country, UW–Madison offers state-of-the-art facilities unmatched by most public universities.

These include the Small Molecule Screening Facility at the UW Comprehensive Cancer Center; the Zeeh Pharmaceutical Experiment Station, which provides consulting and laboratory services for developing formulations and studying solubility, stability and more; the Waisman Clinical Biomanufacturing Facility; the Wisconsin Institute for Medical Research, which provides UW–Madison with a complete translational research facility; and the innovative, interdisciplinary Wisconsin Institutes for Discovery, home to the private, nonprofit Morgridge Institute for Research and its public twin, WID, part of the university's graduate school. The highly qualified experts at these facilities are ready to work with you to create a library of candidates for drug development.