Abstract: Disclosed are novel enamine quaternary compounds of the formula ##STR1## wherein m=1, 2 or 3 and n=1, 2 or 3 with the proviso that m+n=3, 4 or 5; R.sup.1 and R.sup.2 are independently lower alkyl or hydrogen, and R.sup.3 and R.sup.4 are independently selected from the group consisting of lower alkyl, lower cycloalkyl lower alkyl, lower alkenyl, phenyl lower alkyl, thienyl lower alkyl, furyl lower alkyl, lower alkoxy lower alkyl, halogenated lower alkyl, lower alkyloyloxo or lower alkyloyloxy lower alkyl or wherein NR.sup.3 R.sup.4 together comprise a heterocycle ring; and wherein X.sup.- represents a pharmaceutically acceptable anion. Pharmaceutical compositions containing the same when administered to warm-blooded animals exhibit a muscle relaxant effect characterized by excellent onset and recovery times. Also disclosed are methods of making the enamine quaternary compounds.

Abstract: A process is described whereby a synthetically produced 4-styryl-cis-3,4-azetidinone is converted to an isocephalosporin or its 2-oxa analog. The process is based upon the condensation of enamine and imine synthons. Novel intermediate azetidinones are also disclosed. Control of the stereochemical course of the process allows economical, high yield preparation of the racemic form of the product or when a single enantiomer of the imine synthon derived from the .beta.-hydroxy-.alpha.-amino acid starting material is used, both enantiomers of the product may be prepared and separated without optical resolution.