Process for preparing cephalosporins

Details Process for preparing cephalosporins Process for preparing cephalosporins

C - Chemistry, Metallurgy

07

D

260/103

C07D 501/02 (2006.01) C07D 205/095 (2006.01)

Patent

CA 1055485

ABSTRACT OF THE DISCLOSURE A process is disclosed for preparing cephalosporins of structure: Image III where 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; R1 is selected from the class consisting of hydroxyl, alkoxy with 1 to 4 carbon atoms, trichloroethoxy-, benzyloxy-, p-methoxy-benzyloxy-, p-nitrobenzyloxy-, benzhydryloxy-, benzyloxy-, phenylmethoxy-, phenacyloxy-, and p-halophen acyloxy; 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 nitrogen heterocyclic ring; wherein a compound of structure: Image (I') Abstract of the Disclosure continued: is reacted in a suitable solvent at a temperature between -20°C and +80°C, in the presence of an aqueous organic ox inorganic acid with an azoderivative of the formula: a Image where R2 and R3 are equal ox different and represent lower alkyl, a mononuclear aryl ring, CN-, a mononuclear heterocyclic ring, or the radicals -COR4, -COOR4, <IMG, -CONHR4, or R2 and R3 together may represent the residues: Image Image where T represents Image , Image , and R4 is lower alkyl, a mononuclear aryl ring or a mononuclear heterocyclic, ring to give a compound of structure: Image (II') in which R, R1, R2, R3, and Z have the meanings given above, and said intermediate (II') is reacted in a suitable solvent at a temperature between -100° and +120°C with a compound selected from the class consisting of inorganic basic or weakly acid oxides, and inorganic and organic bases, to finally give the desired compound (III) which is isolated and purified in known Abstract of the Disclosure continued: manner. More particularly, a compound of structure: Image (I) is reacted in a suitable solvent at a temperature between -20°C and +80°C, in the presence of an organic and inorganic aqueous acid, with an azoderivative of the formula: Image to give a compound of the formula: Image where V may be hydrogen, or an aliphatic, aromatic, arylaliphatic or acylic residue, or the residues: Image ; Image Image where R, R1, R2, R3, and Z have the meanings given above, and M Abstract of the Disclosure continued: is hydrogen or an alkyl group with 1 to 4 carbon atoms. Also included are the intermediates, which are 2.beta.-thiohydrazoazetidinones of structure: Image where V may be hydrogen, or an aliphatic, aromatic, arylalipha- tic or acyclic residue, and in particular the residues; Image ; Image ; Image and where R, R1, R2, R3, M and Z have the meanings given above.

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