Process for preparing cephalosporins and intermediates

Details Process for preparing cephalosporins and intermediates Process for preparing cephalosporins and intermediates

C - Chemistry, Metallurgy

07

D

260/108

C07D 501/08 (2006.01) C07D 205/095 (2006.01)

Patent

CA 1057284

ABSTRACT OF THE DISCLOSURE A process is disclosed for preparing derivatives of 7-amino-cephalosporanic acid and 7-amino-desacetoxycephalosporanic acid of structure: Image (V) were R1 is selected from the class consisting of hydroxyl, alkoxy with 1 to 4 carbon atoms, trichloroethoxy, benzyloxy, p-methoxy- benzyloxy, p-nitrobenzyloxy, benzhydryloxy, triphenylmethoxy, phenacyloxy, and p-halophenacyloxy; Z is selected from the class consisting of hydrogen, hydroxyl, -O-alkyl, -O-CO-alkyl, -Br, -I. -N3, -NH2, -O-CO-CH3, O-CO-NH2, and an S-mononuclear hetero- cyclic ring, starting from a 3-acylamino-2.beta.-thiohydrazoazetidinone structure: Image (II') were R is selected from the class consisting of hydrogen, alkyl having from 1 to 4 carbon atoms, cyano-methyl, thienyl-methyl, furyl-methyl, naphthyl-methyl, phenyl-methyl, phenoxy-methyl, phenyl-isopropyl, phenoxy-isopropyl, pyridyl-4-thiomethyl, and tetrazolyl-1-methyl; R2 and R3 are equal or different and represent a lower alkyl, a mononuclear aryl ring, CN, a mononuclear hetero- cyclic ring or the radicals -COR4, -COOR4, -?- (OR4)2, -CONHR4, Abstract continued ... or R2 and R3 together may represent the residues: Image where T represents Image , Image ; and R4 is a lower alkyl, a mononuclear aryl ring or a mononuclear heterocyclic ring, wherein the compound (II') is reacted with a phosphorous halide such as phosphorus pentachloride or phosphorus oxychloride in the presence of a tertiary amine such as pyridine, the corres- ponding imino chloride is reacted with a lower aliphatic alcohol, the iminoether so formed is hydrolyzed with water in an acid medium, and the resultant 3-amino-2 .beta.-thiohydrazoazetidinone of structure: Image (IV') in which R1, R2, R3 and Z have the meanings given heretofore, is reacted in a suitable solvent and at a temperature between -100° and +120°C with a compound selected from the class con- sisting of inorganic basic or weakly acid oxides and inorganic and organic bases, to finally give the desired compound (V) which is isolated and purified in known manner; 2.beta.-thiohydrazoazeti- dinones are also disclosed as intermediates.

229024

Affiliated with

Also associated with

Rating

Process for preparing cephalosporins and intermediates does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Process for preparing cephalosporins and intermediates, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for preparing cephalosporins and intermediates will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFCA-PAI-O-1144520