An exo-selective synthesis of himbacine analogs

Details An exo-selective synthesis of himbacine analogs An exo-selective synthesis of himbacine analogs

C - Chemistry, Metallurgy

07

D

C07D 307/92 (2006.01) C07C 235/28 (2006.01) C07D 295/18 (2006.01) C07D 317/72 (2006.01) C07D 405/06 (2006.01) C07D 493/10 (2006.01)

Patent

CA 2594807

This application discloses a novel process for the synthesis of himbacine analogs, as well as the compounds produced thereby. The synthesis proceeds by alternative routes including the cyclic ketal amide route, the chiral carbamate amide route, and the chiral carbamate ester route. The compounds produced thereby are useful as thrombin receptor antagonists. The chemistry disclosed herein is exemplified in the following synthesis sequence: (Formulae 8A, 7B).

L'invention concerne un nouveau processus de synthèse d'analogues d'himbacine, ainsi que les composés ainsi produits. La synthèse se déroule par des itinéraires alternatifs comprenant l'itinéraire de l'amide cétal cyclique, l'itinéraire d'amide de carbamate chiral, et l'itinéraire d'ester de carbamate chiral. Les composés ainsi produits sont utilisés en tant qu'antagonistes du récepteur de la thrombine. Le processus de chimie présenté ici est illustré dans la séquence de synthèse suivante (formules 8A, 7B).

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