Improved Potency of Drugs and Pesticides via Novel Difluoromethylation Methods

 

2022-016
   
Technology Overview

Installing fluorine and fluorine-containing groups has become a commonly used tactic to improve the potency of pharmaceutical and agrochemical agents. In particular, difluoromethyl (CF2H) and trifluoromethyl (CF3) groups act as lipophilic hydrogen bond donors and thus potential bioisosteres for hydroxyl, amino, or thiol groups. As a result, CF2H and CF3-containg molecules have received increased attention in medicinal and agricultural chemistry.

Alkyl-difluoromethane and alkyl-trifluoromethane molecules have great pharmaceutical and agrochemical relevance. However, limited methods were available that could install CF2H and CF3 groups selectively at aliphatic sites, especially at late-stage steps.

Dr. Wei Liu has invented reaction methods which can form a diverse range of alkyl-fluoromethanes from alkyl halides, alkenes, alcohols, and carboxylic acids. These reaction methods are scalable and have a broad substrate scope and functional group tolerance, making them great for late-stage modification of complex drug candidates. Thus, with these reaction methods, previously inaccessible pharmaceutical and agrochemical candidates can be easily synthesized.

Background

 

Advantages and Benefits
  • Addition of CF2H groups to alkyl halides, alkenes, alcohols, and carboxylic acids
  • Possibility for new and metabolically stable drug candidates
  • Broad substrate scope and functional group tolerance
  • Applicable to late-stage modification of complex drug candidates
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Patents
Serial No. File Date Patent No. Issued Date
Other Media
Inventor(s)
  • Wei Liu
Contact
Madison Bourbon
Sr. Licensing Associate, Physical Sciences
Lead Inventor