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NEW SYNTHESIS OF REPAGLINIDE

Barbara Szechner 1Osman Achmatowicz Michał Odrowąż-Sypniewski Krzysztof Wiśniewski 

1. Pharmaceutical Research Institute (IF), Rydygiera 8, Warszawa 01-793, Poland

Abstract

Repaglinide (1) belongs to a new class of orally administered drugs for treatment of type 2 diabetes. It was launched in 1997 under brand names Prandin (USA) and NovoNorm (elsewhere). Repaglinide (1) was obtained by several related ways. In each case it involved condensation of (S)-amine 2 with substituted phenylacetic acid 3 and hydrolysis of an ester group in the resulting amide [1].

Rys1.gif

In this communication we report on the new method of repaglinide (1) synthesis [2] rendering preparation of amine 2 unnecessary.

Our approach is based on the improved method of (S,S)-amine 4 preparation, its condensation with an acid 3 yielding amide 5 and removal of an ester group and chiral auxiliary, N-(1-phenyl)ethyl substituent from the latter.

Rys2_1.gif

1. Grell W., Hurnaus R., Griss G., Sauter R., Rupprecht E., Mark M., Luger P., Nar H.,

Wittneben H., Műller P., J.Med.Chem., 1998, 41, 5219-5246; EP 0 589 874 B1.

2. Zgłoszenia patentowe: PL 368 968, 7.07.2004; PL 375 743, 16.06.2005.

 

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Related papers

Presentation: Oral at V Multidyscyplinarna Konferencja Nauki o Leku, by Barbara Szechner
See On-line Journal of V Multidyscyplinarna Konferencja Nauki o Leku

Submitted: 2006-03-02 10:29
Revised:   2009-06-07 00:44