Coupling process and intermediates useful for preparing...

Details Coupling process and intermediates useful for preparing... Coupling process and intermediates useful for preparing...

C - Chemistry, Metallurgy

07

D

C07D 501/18 (2006.01) C07D 501/06 (2006.01) C07D 501/20 (2006.01)

Patent

CA 2436848

This invention relates to a novel process for the preparation of 3-cyclic- ether-substituted cephalosporins of formula (I): wherein the group CO2-R1 is a carboxylic acid or a carboxylate salt and R2 has the formula (a): wherein A1 is selected form the group consisting of C6-10aryl, C1-10heteroaryl and C1- 10heterocyclyl; A2 is selected from the group consisting of hydrogen, C1- 6alkyl, C3-10cycloalkyl, C6-10aryl C1-6alkyl(CO)(C1-6)alkyl-O-, HO(CO)(C1- 6)alkyl, mono-(C6-10aryl)(C1-6alkyl), di-(C6-10aryl)(C1-6alkyl) and tri-(C6- 10aryl)(C1-6alkyl); from a zwitterionic compound of formula (II), or from a compound of formula (V): wherein R2 is as defined above and R3 is para- nitrobenzyl or allyl. The invention also relates to the preparation of the above compounds of formula (II) and (V).

La présente invention concerne un procédé permettant la préparation de céphalosporines substituées en éther cyclique en position 3 de formule (I): dans laquelle le groupe CO¿2?R?1¿ est un acide carboxylique ou un sel carboxylate et R?2¿ est représenté par la formule (a): dans laquelle A?1¿ est sélectionné dans le groupe constitué par C¿6-10? aryle, C¿1-10 ?hétéroaryle et C¿1-10 ?hétérocyclyle; A?2¿ est sélectionné dans le groupe constitué par hydrogène, C¿1-6? alkyle, C¿3-10 ?cycloalkyle, C¿6-10 ?aryle, C¿1-6 ?alkyle (CO)(C¿1-6?)alkyle-O-, HO(CO)(C¿1-6?)alkyle, mono-(C¿6-10 ?aryle) (C¿1-6 ?alkyle), di-(C¿6-10 ?aryle) (C¿1-6 ?alkyle) et tri-(C¿6-10 ?aryle) (C¿1-6? alkyle). Ce procédé est mis en oeuvre à partir d'un composé zwittérionique de formule (II), ou d'un composé de formule (V): dans laquelle R?2¿ est tel que défini ci-dessus et R?3¿ est para-nitrobenzyle ou allyle. Ladite invention concerne également la préparation des composés ci-dessus de formules (II) et (V).

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