Efficient Catalytic Production of Isoamines for Pharmaceutical Applications
A number of compounds used as intermediates in drug manufacture are difficult to produce. One such class of compounds is iminoamines. It would be desirable to have a way of easily manufacturing a wide variety of substituted iminoamines with good regioselectivity. This capability would make possible the production of a wide variety of chemical intermediates used in potential drug discovery and current drug manufacture, and thus would be of interest to pharmaceutical customers.
Description of Technology
This invention uses a titanium metal catalytic complex to couple three simple starting materials in a single step to produce one or more substituted iminoamines, in particular beta-unsaturataed beta-iminoamines. The three starting materials are one or more primary amines, alkynes and isonitriles. The advantage of this is that using combinatorial methodology, relatively few starting materials may be combined to generate a large library of compounds for testing in a specific application. Second, the products are highly unsymmetrical and a single isomer is often generated. Synthesis of these products using current methods would require several synthetic steps. The method of this invention may allow the production of products that are inaccessible using more traditional strategies.
- Reduced production costs: The produced compounds can be produced more cheaply with a smaller number of steps than with existing processes.
- Selectivity in catalyzed product: The process affords good control on regioselectivities.
- Improved production efficiencies: The process cuts down on manpower and on material costs.
- New production opportunities: The process promises an increased ability to maximize the molecular complexity of the products in a single synthetic step.
- Environmental benefits: The process cuts down on waste streams.
This process promises a rapid and inexpensive means for producing useful iminoamine-based chemicals, the end application of these chemicals being in the production of existing and new pharmaceuticals. The process would also enable large libraries of iminoamine-based products to be constructed from relatively few starting materials which can be screened for useful pharmaceutical chemicals.
US 6,861,559 B2 (issued 03/01/05)
For Information, Contact:
Michigan State University