Methods for the preparation of benzoxazole sulfonamide...

C - Chemistry – Metallurgy – 07 – D

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C07D 263/58 (2006.01)

Patent

CA 2537877

The present invention relates to methods for the preparation of benzoxazole sulfonamide compounds of formula (9) as well as novel intermediates of formula (6) for use in said method. More in particular the invention relates to methods for the Preparation of 2-amino-benzoxazole sulfonamide compounds which make use of 2-mercapto-benzoxazole sulfonamide intermediates, more in particular methods employing the intermediate 1-Benzy1-2-hydroxy-3- [isobutyl~(2-methylsulfanyl-benzoxazole-6-sulfonyl)-amino)-propyl)-carbamic ester, and to methods amenable to industrial scaling up. Said benzoxazole sulfonamide compounds are particularly useful as HIV protease inhibitors. The substituents are defined in the claims.

La présente invention a trait à des procédés pour la préparation de composés sulfonamide de benzoxazole de formule (9) ainsi qu'à des intermédiaires de formule (6) destinés à être utilisés dans lesdits procédés. De manière plus spécifique, l'invention a trait à des procédés pour la préparation de composés sulfonamide de 2-amino-benzoxazole qui mettent en oeuvre des intermédiaires sulfonamide de 2-mercapto-benzoxazole, plus particulièrement des procédés utilisant l'intermédiaire d'ester carbamique de1-benzyl-2-hydroxy-3-[isobutyl-(2-méthylsulfanyl-benzoxazole-6-sulfonyl)-amino)-propyle, et à des procédés aptes à être mis en oeuvre à l'échelle industrielle. Lesdits composés de sulfonamide de benzoxazole sont particulière utiles en tant qu'inhibiteurs de la protéase du VIH Les substituants sont tels que définis dans les revendications..

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