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AssigneeToyama Chemical Co., Ltd.
InventorsIsamu Saikawa, Shuntaro Takano, Kaishu Momonoi, Isamu Takakura, Chiaki Kutani, Kiyoshi Tanaka, Kenshin Hayashi
Estimating the term…
The N,N-dimethylacetamide adduct of 7-[D(-)-.alpha.-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-.alpha.-(4-hyd roxyphenyl)acetamido]-3-[5-(1-methyl-1,2,3,4-tetrazolyl)thiomethyl]-.DELTA. .sup.3 -cephem-4-carboxylic acid, a process for the production thereof, and a process for producing said acid and a pharmaceutically acceptable salt thereof through said adduct.
A process for producing the N,N-dimethylacetamide adduct of 7-[D(-)-.alpha.-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-.alpha.-(4-hyd roxyphenyl)acetamido]-3-[5-(1-methyl-1,2,3,4-tetrazolyl)thiomethyl]-.DELTA. .sup.3 -cephem-4-carboxylic acid represented by the formula (I), ##STR6## which comprises acylating the cephem compound represented by the formula (III), ##STR7## at the 7-amino group of said cephem compound (III), with a reactive derivative of the compound represented by the formula (IV), ##STR8## under anhydrous conditions in the presence of N,N-dimethylacetamide as the solvent for the said compounds (III) and (IV) to produce a solution of the acylated product and recovering the said adduct (I) as a precipitate from the solution.
A process for producing 7[D(-)-.alpha.-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-.alpha.-(4-hydr oxyphenyl)-acetamido]-3-[5-(1-methyl-1,2,3,4-tetrazolyl)thiomethyl]-.DELTA. .sup.3 -cephem-4-carboxylic acid represented by the formula (II), ##STR9## which comprises treating the N,N-dimethylacetamide adduct of 7-[D(-)-.alpha.-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-.alpha.-(4-hyd roxyphenyl)acetamido]-3-[5-(1-methyl-1,2,3,4-tetrazolyl)thiomethyl]-.DELTA. .sup.3 -cephem-4-carboxylic acid represented by the formula (I), ##STR10## with a solvent for N,N-dimethylacetamide to remove the N,N-dimethylacetamide and to liberate compound (II).
A process for producing 7-[D(-)-.alpha.-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-.alpha.-(4-hyd roxyphenyl)-acetamido]-3-[5-(1-methyl-1,2,3,4-tetrazolyl)thiomethyl]-.DELTA ..sup.3 -cephem-4-carboxylic acid represented by the formula (II), ##STR11## which comprises acylating the cephem compound represented by the formula (III), ##STR12## at the 7-amino group of said cephem compound (III), with a reactive derivative of the compound represented by the formula (IV), ##STR13## under anhydrous conditions in the presence of N,N-dimethylacetamide as the solvent for the said compounds (III) and (IV) to produce a solution of the acylated product, recovering as a precipitate the resulting compound represented by the formula (I), ##STR14## and treating said compound (I) with a solvent for N,N-dimethylacetamide to remove the N,N-dimethylacetamide and to liberate compound (II).
A process for producing purified 7-[D(-)-.alpha.-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-.alpha.-(4-hyd roxyphenyl)-acetamido]-3-[5-(1-methyl-1,2,3,4-tetrazolyl)thiomethyl].DELTA. .sup.3 -cephem-4-carboxylic acid represented by the formula (II), ##STR15## which comprises dissolving in dimethylacetamide the compound represented by the formula (II) associated with the by-products of its prior syntheses and thereafter precipitating from said solution the N,N-dimethylacetamide adduct of 7-[D(-)-.alpha.-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-.alpha.-(4-hyd roxyphenyl)acetamido]-3-[5-(1-methyl-1,2,3,4-tetrazolyl)thiomethyl]-.DELTA. .sup.3 -cephem-4-carboxylic acid represented by the formula (I), ##STR16## and then treating the N,N-dimethylacetamide adduct of the formula (I) with a solvent for N,N-dimethylacetamide to remove the N,N-dimethylacetamide and to liberate purified compound (II).
Dependencies are inferred from the claim text.