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The Facile Synthesis of Trifluoromethyl Ethers of Pharmaceutically Useful Monomers

Request Number N724418
Author
Need details
Description

Pfizer's Worldwide R&D organization wishes to pursue potential research collaborations with academic organisations and biotechnology companies that have synthetic chemistry expertise to develop facile and practical methods of forming aromatic, heteroaromatic and alkyl trifluoromethyl ethers of medicinally useful molecules, including trifluoromethyl ether monomers. Such methods will ultimately be suitable for use within a pharmaceutical laboratory.

 

Background

The incorporation of fluorine into molecules of medicinal interest is of great importance in the pharmaceutical industry.  Lipitor®, Celebrex® and Januvia® are three of the many examples of marketed drugs which contain either a fluorine or trifluoromethyl group. Fluorine and fluorine-containing substituents are often used to enhance a molecule’s pharmacokinetic behaviour and/or target binding potency. Although synthetic methods for preparing fluorine-containing compounds exist, there is still a need for mild, general synthetic protocols that improve and expand the scope of fluorine incorporation.

 

One area of developmental need is the discovery of mild and general protocols for synthesizing aromatic, heteroaromatic and alkyl trifluoromethyl ethers.  Published examples for the synthesis of trifluoromethyl ethers suffer from multiple drawbacks; including the use of multi-step protocols, a lack of generality and limited functional group compatibility.

 

Key Success Criteria

Preferred research proposal(s) from potential partners must be able to:

 

  • Present a scientifically rational proposal that seeks to provide a practical, general protocol for synthesizing trifluoromethyl ethers including aryl-O-CF3, heteroaryl-O-CF3, alkyl-O-CF3, aryl-CH2-O-CF3 or heteroaryl-CH2-O-CF3 moieties;

  • Develop a synthetic method that requires only standard lab conditions, standard glassware and standard equipment;

  • Develop a synthetic method using readily available or readily prepared starting materials such as aromatic/heteroaromatic halides, alcohols or boronic acids/esters for preparing Het/Ar-O-CF3, or alkyl-OH for preparing alkyl-O-CF3 monomers; and

  • Develop a synthetic method that allows moderate to good functional group compatibility.

 

Possible Approaches

Pfizer seeks proposals for developing facile and practical methods of forming aromatic, heteroaromatic and alkyl trifluoromethyl ethers of medicinally useful molecules, including trifluoromethyl ether monomers that can be used in analogue preparation.

 

Acceptable proposals may include protocols that utilize readily available starting materials that contain common synthetic handles such as halides, alcohols or other common functional groups.

 

Of specific interest are methods for trifluoromethyl ether incorporation into compounds that contain Lewis basic and/or weakly basic substituents including heterocycles, amides, nitriles, ethers, for example.

 

An example of a desirable reaction is illustrated below:

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Pfizer is seeking a collaborative research partner(s) and all details of agreement will be negotiated between Pfizer and the potential solution provider (or the relevant institutional technology transfer office). Selected proposal(s) will be submitted to an internal panel composed of members of Pfizer Worldwide Research and Development for endorsement and funding to support the work in the potential partners’ laboratories.

 

If able, Pfizer may provide to the potential selected partner(s) monomers of pharmaceutical interest from its database of commercially available chemicals.  Monomers from Pfizer’s dry store, that are commercially available, could be available for use if they are not key intermediates in any current Pfizer program.

 

Approaches not of interest


 

The following approaches are not of interest:

 

  • Protocols that require the use of non-standard industrial laboratory equipment such as glove-boxes, Schlenk-ware, or Teflon vessels; or

  • Protocols that require the use of reagents that are highly toxic or explosive.

 

Preferred Collaboration types
  • To Be Negotiated
Items to be submitted

We are looking for a concise abstract/executive summary.  The proposal should include a completed required Response Template to briefly describe the technical approach and provide information on technology performance, background and description of the responding team and their related experience.

 

By submitting a response you represent that the response does not contain and will not be deemed to contain any confidential information of any kind whatsoever. All Personal Information disclosed to Pfizer within a response will be utilized in accord with principles and polices as described at http://www.pfizer.com/general/privacy. By submitting a response, you also acknowledge and confirm that you have consulted with your Technology Transfer Office, Business Development Office or any other required group and that you have their approval to submit the response. By submitting a response, you acknowledge that the Need's sponsoring organization, in its sole discretion, may select or reject a response or any portion thereof.

 

Your NineSights community profile should contain all required information in order to provide us with appropriate contact information for your responses. For questions about NineSights privacy and security, please feel free to post in our forum.

 

Point of Contact
Darren Coomber
Area of Interest
  • Medical Products & Services
Organization
Pfizer
Due Date
August 26, 2014
Award Amount
TBD
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