Process for the preparation of 4,5-diamino shikimicacid

Details Process for the preparation of 4,5-diamino shikimicacid Process for the preparation of 4,5-diamino shikimicacid

C - Chemistry, Metallurgy

07

C

C07C 229/48 (2006.01) C07C 227/10 (2006.01) C07C 227/18 (2006.01)

Patent

CA 2577192

The present invention relates to a process for the preparation of a 4,5- diamino shikimic acid derivative of formula (I) and pharmaceutically acceptable addition salts thereof wherein R1, R1~ are independent of each other H or alkyl, R2 is an alkyl and R3, R4 are independent of each other H or an alkanoyl, with the proviso that not to both R3 and R4 are H. 4,5-diamino shikimic acid derivatives of formula I, especially the (3R,4R,5S)-5~-amino-4- acetylamino-3- (1-ethyl-propoxy)-cyclohex-l-ene-carboxylic acid ethyl ester and its pharmaceutically acceptable additional salts are potent inhibitors of viral neuraminidase.

L'invention concerne un procédé permettant de préparer un dérivé d'acide 4,5-diamino shikimique représenté par la formule (I) et leurs sels addition pharmaceutiquement acceptables. Dans la formule (I), R1, R1' représentent indépendamment l'un de l'autre H ou alkyle; R2 représente alkyle; et R3, R4 représentent indépendamment l'un de l'autre H ou un alcanoyle à condition qu'à la fois R3 et R4 représentent H. Les dérivés d'acide 4,5-diamino shikimique représentés par la formule (I), en particulier, l'éthylester d'acide (3R,4R,5S)-5--amino-4-acetylamino-3- (1-ethyl-propoxy)-cyclohex-l-ene-carboxylique et ses sels addition pharmaceutiquement acceptables sont des inhibiteurs potentiels de la neuraminidase virale.

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