4-cyano-2-azetidinones and production thereof

Details 4-cyano-2-azetidinones and production thereof 4-cyano-2-azetidinones and production thereof

C - Chemistry, Metallurgy

07

D

260/302, 260/335

C07D 205/08 (2006.01) C07D 205/085 (2006.01) C07D 403/12 (2006.01) C07D 409/14 (2006.01) C07D 417/12 (2006.01) C07F 7/08 (2006.01) C07F 7/10 (2006.01)

Patent

CA 1212112

Abstract 4-Cyano-2-azetidinone derivatives represented by the formula Image [I] wherein R1 is an amino group which may be acylated or protected, X is a hydrogen atom or a methoxy group and W is a hydrogen atom or a sulfo group, and methods of producing the same, for example, as represented by Image [I] , and [I] Image wherein R2 is an acylated or protected amino group, Y is a halogen atom or a group having the formula -OCOR3, -SCOR3 or -S(O)n-R3 (R3 being a hydrocarbyl group and n an integer 1 or 2), R4 is an amino group which may be acylated or protected and X is as defined above. Compounds [I] are useful as advantageous intermediates for the synthesis of optically active 4-substituted-2-azetidinone derivatives, and, when W=SO3H, [I] are also useful as antimicrobial agents and as beta-lactamase inhibitors.

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