Process for the production of cephem compounds

Details Process for the production of cephem compounds Process for the production of cephem compounds

C - Chemistry, Metallurgy

07

D

260/103

C07D 501/06 (2006.01) C07D 213/70 (2006.01) C07D 257/04 (2006.01) C07D 333/24 (2006.01)

Patent

CA 1050968

ABSTRACT OF THE DISCLOSURE A process for the production of a cephem compound of the formula Image ( I) wherein R is a hydrogen atom; a free or protected amino group of the formula -NHA where A is a hydrogen atom or a known amino-protecting group subsequently cleavable from the amino group; a carboxyl or carboxylate group of the formula -COOB where B is a hydrogen atom or an organic or inorganic cation; a formamido group of the formula -NHCHO; or a free or protected hydroxyl group of the formula -OD -where D is a hydrogen atom or a known hydroxyl- protecting group cleavable from the hydroxyl group or is an alkanoyl group, aralkanoyl group or aroyl group which may be substituted with a halogen atom or nitro group; Rl is a hydrogen atom; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted alkoxyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted aralkyloxy group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted cycloalkenyl group; a substituted or unsubstituted alkylthio group; a sub- stituted or unsubstituted arylthio group; a substituted or unsubstituted heterocyclic thio group; cyano group; a substituted or unsubstituted heterocyclic group containing or not containing a condensed ring; or a substituted or unsubstituted aryl group containing a condensed ring: R2 is a hydrogen atom; a substituted or unsubstituted alkyl group; a substituted or un- substituted aryl group; a substituted or unsubstituted alkoxyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted aralkyloxy group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted cycloalkenyl group; a sub- stituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthio group; a substituted or un- substituted heterocyclic thio group; cyano group; a substituted or unsubstituted heterocyclic group containing or not containing a condensed ring; a substituted or unsubstituted aryl group containing a condensed ring; a halogen atom; azido group; a dialkylamino group; a substituted or unsubstituted diarylamino group; a sub- stituted or unsubstituted alkoxycarbonyl group; or a substituted or unsubstituted alkanoyl group: or R1 and X2 taken together with the carbon atom attached to both R1 and R2 form a cyclic ring: or R1 and R2 taken together form an alkylidene or arylidene group R3 is a hydrogen atom; acetoxy group; azido group; cyano group; a sub- stituted or unsubstituted alkoxyl group; a substituted or unsubstituted aroyloxy group; a substituted or unsub- stituted aralkyloxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthio group; a substituted or unsubstituted aralkylthio gruop; or a substituted or unsubstituted heterocyclic thio group: and M2 is an alkali metal cation, an ammonium cation or a hydrogen atom, which comprises reacting a compound of the formula Image ( II) wherein R1 and R2 are each as defined above, R' is the same as R except that R' does not denote the free amino or free hydroxyl group 9 and Ml is an inorganic or organic cation, with a 7-aminocephalosporanic acid derivative of the formula Image ( III) wherein R3 and M2 are each as defined in the above, in a homogeneous aqueous solution of these two reactants 9 to prepare a reaction product of the formula Image ( I') wherein R', R1, R2, R3 and M2 are each as defined in the above, and where R' denotes the protected amino or protected hydroxyl group, optionally removing the amino- protecting group A or the hydroxyl-protecting group D from the reaction product of the formula (I').

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