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Enantiomerically pure chiral N-Acyl-alpha-aminonitriles

Country of Origin: Germany
Reference Number: TODE20161110001
Publication Date: 17 November 2016

Summary

A German university developed a novel method for the chemical production of enantiomerically pure chiral N-acyl-α-aminonitriles or N-sulfonyl-α-aminonitriles, active in pharmaceutical ingredients against diabetes type 2. The method does not need toxic reagents. The university offers a license agreement as well as a technical cooperation agreement to industrial partners.

Description

Enantiomerically pure N-acyl-a-aminonitriles have gained interest in the pharmaceutical industry these days since a range of recently developed pharmaceuticals are based on this product class. Prominent examples are Vildagliptin®, Saxagliptin® or NVP-DPP-728, which are active pharmaceutical ingredients against diabetes type II and at least two of them are already successfully on the market. Important precursors of these so-called “gliptins” are synthesized via multiple phase reactions as state of the art and typical strategies towards such types of molecules are based on toxic reagents such as cyanides or Vilsmeier reagents. Furthermore, the production of the latter one includes toxic precursors like oxalylchloride and phosphorylchloride. Currently, e.g. the synthesis of Vildagliptin® starts from an enantiomerically pure amino acid (here L-proline), which is transformed first into an amide derivative and then via Vilsmeier reagent into the nitrile product (process by Novartis).

A German university invented a production process which avoids the need of such toxic reagents. In addition, it has the advantage that the reaction can be conducted under mild conditions. The innovative reaction is also using amino acids as precursors but they are then transformed via an aldehyde intermediate into its corresponding aldoxime, which subsequently is transformed via a chemocatalytic dehydration to the nitrile target molecule.
The described technology enables a safe, fast and competitive chemical production of specific N-acyl-α-aminonitriles or N-sulfonyl-α-aminonitriles, serving as intermediates for the synthesis of, e.g., Vildagliptin®.

The university offers a license agreement as well as a technical cooperation agreement to pharmaceutical or chemical enterprises. A technical cooperation could include the implementation, repectively adaptation of this alternative technology to the existing production process of a company.

Advantages and Innovations

Compared to the current proceedings the herewith presented invention avoids the need of toxic reagents to produce the intermediates for the synthesis of gliptins. Other competitive advantages are:
- Enantiomerically pure Gliptin derivatives
- New optimized chemocatalytic route
- New approach for important precursors, e.g., of Vildagliptin® or Saxagliptin®
- Starting material easy accessible and avoiding cyanide or Vilsmeier reagents as toxic reagents

Stage Of Development

Field tested/evaluated

Stage Of Development Comment

Yields are strongly fluctuating depending on the type of substance to be produced; at best 92%. This innovative process primarily addresses the avoidance of toxic reagents and intermediates.

Requested partner

The university offers a license agreement as well as a technical cooperation agreement. The offer addresses in particular pharmaceutical enterprises and possibly large chemical enterprises, who produce pharmaceutical ingredients.  But also small chemical enterprises, who offer these substances as part of a research tool, are potential partners.

A technical cooperation could include the implementation and adjustment of this alternative technology to the existing production process of a company.

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