C - Chemistry – Metallurgy – 07 – C
Patent
C - Chemistry, Metallurgy
07
C
C07C 231/00 (2006.01)
Patent
CA 2354476
Methods for the synthesis of .alpha.-hydroxy-.beta.-amino acid and amide derivatives and .alpha.-ketoamide derivatives and novel derivatives made by these methods are provided. These methods involve reacting an N-terminally blocked (protected) aminoaldehyde with an isonitrile and a carboxylic acid to give an amino-.alpha.-acyloxy carboxamide. The acyloxy group may be removed to give the derivative. Alternatively the protecting group is removed and acyl shift occurs to give the derivative. These derivatives are useful in the synthesis of compounds such as peptidyl .alpha.-ketoamides and .alpha.-hydroxy- .beta.-carboxylic acid and amide derivatives. Certain of these compounds have been reported to have activity as inhibitors of proteases, such as serine proteases and cysteine proteases.
L'invention concerne des procédés pour synthétiser l'acide alpha-hydroxy-bêta-amino et des dérivés amides ainsi que des dérivés d'alpha-cétoamide, de même que les nouveaux dérivés obtenus par ces procédés. Ces procédés consistent à faire réagir un amino-aldéhyde bloqué (protégé) en terminaison N avec un isonitrile et un acide carboxylique pour produire un carboxamide amino-alpha-acyloxy. Le groupe acyloxy peut être retiré pour donner un dérivé. En variante, le groupe protecteur est retiré et un décalage d'acyle se produit pour donner le dérivé. Ces dérivés sont utiles dans la synthèse de composés tels que des peptidyl-alpha-cétoamides ou l'acide alpha-hydroxy-bêta-carboxylique et des dérivés amides. Certains de ces composants seraient des inhibiteurs de protéases telles que les protéases de sérine et de cystéine.
Levy Odile E.
Semple Joseph E.
Corvas International Inc.
Smart & Biggar
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