Chiral derivatives of hydroxyphenylglycine and their use in...

Details Chiral derivatives of hydroxyphenylglycine and their use in... Chiral derivatives of hydroxyphenylglycine and their use in...

C - Chemistry, Metallurgy

12

P

C12P 13/04 (2006.01) C07C 225/16 (2006.01) C07C 229/36 (2006.01) C07C 237/20 (2006.01) C07C 237/22 (2006.01) C07C 275/24 (2006.01) C12P 41/00 (2006.01)

Patent

CA 2211827

The chiral derivatives of hydroxyphenylglycin, with the configuration D, have general formula (I), wherein R is H, hydroxy, chloride, -NH2, -NHW, wherein W is an alkyl C1-C4 or aryl group, -OR', wherein R' is an alkyl C1-C4 group, and Z is H, -CONH2 and -C(CH3)=CHCOOY, wherein Y is methyl or ethyl. One of said compounds, D-(-)-2-(2'-hydroxyphenyl)glycin, may be obtained by enzymatic process from the corresponding hydantoin while the others may be obtained by chemical or enzymatic process. The compounds of formula (I) are useful for the production of drugs, particularly for semisynthetic penicillins, cephalosporins, non steroid and mucolytic antiinflammatory agents.

Les dérivés chiraux d'hydroxyphénylglycine, avec la configuration D, ont la formule générale (I), dans laquelle R représente H, hydroxy, chlorure, -NH¿2?, -NHW, où W est un groupe alkyle C¿1?-C¿4? ou aryle, -OR' où R' est un groupe alkyle C¿1?-C¿4?, et Z représente H, -CONH¿2? et -C(CH¿3?)=CHCOOY où Y représente méthyle ou éthyle. L'un de ces composés, D-(-)-2-(2'-hydroxyphenyl)glycine, peut être obtenu par procédé enzymatique à partir de l'hydantoïne correspondante tandis que les autres composés peuvent être obtenus par procédé chimique ou enzymatique. Les composés de la formule (I) sont utiles pour la production de produits pharmaceutiques, en particulier pour les pénicillines semi-synthétiques, les céphalosphorines, les anti-inflammatoires non stéroïdes et mucolytiques.

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