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US 6,555,680 B1Granted
Method for the preparation of ceftiofur sodium
AssigneeOrchid Chemicals & Pharmaceuticals Limited
InventorsPandurang Balwant Deshpande, Pramod Narayan Deshpande, Milind Ramkrishna Kulkarni, Parven Kumar Luthra
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Abstract
The present invention relates to a process for the preparation of sodium salt of Ceftiofur as given in Formula I, directly from its amine salt using sodium base.
Claims22
A process for preparing Ceftiofur sodium of formula (I)
- said process comprising the steps of:
- (a) condensing 3-[2-(furylcarbonyl)thiomethyl]-3-cephem-4-carboxylic acid represented by formula (II) with 5-phenyl-1,3,4-oxadiazole-2-thio-2-(2-aminothiazol-4-yl)2-methoxyimino)acetate represented by formula (III) in a mixture of water and an organic solvent, in the presence of an amine base at a pH range of 7.0 to 8.5
- an at a temperature between −25° C. and 30° C. and subsequent extraction with a solvent selected from dichloromethane or ethylacetate, to obtain Ceftiofur amine salt in aqueous phase,
- (b) treating the aqueous solution of Ceftiofur amine salt of step (a) with charcoal, filtering and evaporating the aqueous solution by employing an evaporation technique under vacuum to remove water to yield a slurry of Ceftiofur amine salt, and (c) treating the slurry of step (b) containing Ceftiofur amine salt with sodium base and precipitating and isolating Ceftiofur sodium by adding organic solvent, followed by filtering the precipitated solid and drying the filtered solid.
1 more element
A process for preparing Ceftiofur sodium of formula (I)
- said process comprising the steps of:
- (a) condensing 3-[2-(furylcarbonyl)thiomethyl]-3-cephem-4-carboxylic acid represented by formula (II) with 5-phenyl-1,3,4-oxadiazole-2-thio-2-(2-aminothiazol-4-yl)-2-methoxyimino)acetate represented by formula (III) in a mixture of water and an organic solvent, in the presence of an amine base at a pH range of 7.0 to 8.5
- and at a temperature between −25° C. and 30° C. and subsequent extraction with a solvent selected from dichloromethane or ethylacetate to obtain Ceftiofur amine salt in aqueous phase;
- (b) adding an organic solvent to the aqueous solution of Ceftiofur amine salt of step (a) and neutralizing the mixture with a stoichiometric amount of a mineral acid;
- and
- (c) adding sodium chloride to separate an organic layer which is treated with charcoal, filtered and treated with a sodium base to precipitate Ceftiofur sodium followed by filtering the precipitated solid and drying the filtered solid.
3 more elements
Dependencies are inferred from the claim text.