Method of preparing phosphodiesterase iv inhibitors

Details Method of preparing phosphodiesterase iv inhibitors Method of preparing phosphodiesterase iv inhibitors

C - Chemistry, Metallurgy

07

D

C07D 213/30 (2006.01) C07D 213/36 (2006.01) C07D 213/38 (2006.01) C07D 213/54 (2006.01)

Patent

CA 2253279

A process for the preparation of Phosphodiesterase IV inhibitors of structural formula VIII, wherein R' is (substituted) phenyl, is described. The process consists of eight chemical steps involving five isolations to prepare the title compound from readily available isovanillin in 35 % overall yield (Scheme 1). The process is highlighted by: a) a highly diastereoselective Michael addition of phenyllithium using (1R, 2S) cis-aminoindanol as a chiral auxiliary, b) highly crystalline intermediates providing for efficient purifications, c) crystallization of the final compound as its CSA salt for excellent enantiomeric purity.

L'invention concerne un procédé servant à préparer des inhibiteurs de phosphodiestérase IV ayant la formule développée VIII dans laquelle R' est phényle (substitué). Le procédé consiste en huit étapes chimiques et utilise cinq étapes d'isolation pour préparer le composé du titre à partir d'isovanilline facile à obtenir, selon un rendement global de 35 % (combinaison 1). Le processus est caractérisé par: a) une addition de Michael de phényllithium à haute diastéréosélectivité utilisant (1R, 2S) cis-aminoindanole comme auxiliaire chiral; b) des intermédiaires fortement cristallins permettant des purifications efficaces; c) une cristallisation du composé final sous forme de son sel de CSA qui permet d'obtenir une excellente pureté énantiomorphe.

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