Process for the preparation of compounds having ace...

Details Process for the preparation of compounds having ace... Process for the preparation of compounds having ace...

C - Chemistry, Metallurgy

07

K

C07K 5/062 (2006.01) C07D 209/42 (2006.01) C07D 209/52 (2006.01) C07D 217/26 (2006.01) C07D 233/36 (2006.01) C07D 233/61 (2006.01) C07D 285/12 (2006.01) C07D 453/06 (2006.01) C07D 495/10 (2006.01) C07D 521/00 (2006.01) C07K 5/02 (2006.01)

Patent

CA 2170872

There is disclosed a process for the preparation of compounds having ACE inhibitory action of the formula Image wherein R has the meanings as in claim 1, wherein the stereospecific amino acid N-[1-(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine is carboxylically activated with a thionyl chloride derivative wherein at least one chlorine atom is replaced by the residue of a heterocyclic ambident compound such as imidazole, benzimidazole, 2-methylimidazole or triazole, especially chlorothionylimidazole or thionyldi- imidazole, in the presence of an organic solvent to the intermediate novel compound A or to the intermediate novel compound B and the obtained intermediate com- pound is reacted with an amino acid, preferably in the monosilylated form, most preferably in the disilylated form. Disclosed are also novel compounds useful as start- ing materials or intermediates in the present process.

Procédé de préparation de composés à activité inhibitrice d'ACE de formule (1) où R est défini dans la revendication 1, où l'acide aminé stéréospécifique N-[1-(S)-éthoxycarbonyl-3-phénylpropyl]-L-alanine est activé au niveau de son groupe carboxyle par un dérivé du chlorure de thionyle où au moins un atome de chlore est remplacé par le reste d'un composé hétérocyclique ambident tel que l'imidazole, le benzimidazole, le 2-méthylimidazole ou le triazole, et en particulier tel que le chlorothionylimidazole ou le thionyldiimidazole en présence d'un solvant organique des nouveaux composés intermédiaires A et B, on fait ensuite réagir le composé intermédiaire obtenu avec un acide aminé, de préférence de la forme monosilylée ou mieux de la forme disilylée. Sont également présentés de nouveaux composés servant de produits de départs ou d'intermédiaires dans le procédé susdit.

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