Pyroglutamate salts and their use in the optical resolution...

Details Pyroglutamate salts and their use in the optical resolution... Pyroglutamate salts and their use in the optical resolution...

C - Chemistry, Metallurgy

07

D

C07D 295/088 (2006.01) C07D 207/28 (2006.01)

Patent

CA 2599498

The present invention relates to (S)-2-[4-(4-chlorobenzhydryl)piperazin-1-yl]- ethoxyacetamide - (S)-pyrrolidone-5-carboxylic acid salt; (R)-2-[4-(4- chlorobenzhydryl)piperazin-1-yl]-ethoxyacetamide - (S)-pyrrolidone-5- carboxylic acid salt; (S)-2-[4-(4-chlorobenzhydryl)piperazin-1-yl]- ethoxyacetamide - (R)-pyrrolidone-5-carboxylic acid salt; or (R)-2-[4-(4- chlorobenzhydryl)piperazin-1-yl]-ethoxycetamide - (R)-pyrrolidone-5-carboxylic salt. The present invention relates also to a process for preparing (S)-2-[4- (4-chlorobenzhydryl)piperazin-1-yl]-ethoxyacetamide (I) and (R)-2-[4-(4- chlorobenzhydryl) piperazin-1-yl]-ethoxyacetamide (II) by chemical resolution of a mixture. These compounds are respectively intermediates for the synthesis of dextrocetirizine and levocetirizine.

La présente invention concerne un sel d'acide (S)-2-[4-(4-chlorobenzhydryl)pipérazin-1-yl]-éthoxyacétamide-(S)-pyrrolidone-5-carboxylique ; un sel d'acide (R)-2-[4-(4-chlorobenzhydryl)pipérazin-1-yl]éthoxyacétamide-(S)-pyrrolidone-5-carboxylique ; un sel d'acide (S)-2-[4-(4-chlorobenzhydryl)pipérazin-1-yl]éthoxyacétamide-(R)-pyrrolidone-5-carboxylique ; ou un sel d'acide (R)-2-[4-(4-chlorobenzhydryl)pipérazin-1-yl]éthoxyacétamide-(R)-pyrrolidone-5-carboxylique. La présente invention concerne également un procédé servant à préparer du (S)-2-[4-(4-chlorobenzhydryl)pipérazin-1-yl]éthoxyacétamide (I) et du (R)-2-[4-(4-chlorobenzhydryl)pipérazin-1-yl]éthoxyacétamide (II) par résolution chimique d'un mélange. Ces composés sont des intermédiaires pour la synthèse de la dextro-cétirizine et de la lévo-cétirizine, respectivement.

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