【药物名称】DQ-2556
化学结构式(Chemical Structure):
参考文献No.2824
标题:Cephalosporin derivs., process for preparing them and pharmaceutical compsns. containing them
作者:Furukawa, M.; Tagawa, H.; Hayano, T.; Ejima, A. (Daiichi Pharmaceutical Co., Ltd.)
来源:AU 8541333; EP 0159011; ES 8607319; JP 1985222490; JP 1986007280
合成路线图解说明:

By condensation of 3-(acetoxymethyl)-7-[2-(2-aminothiazol-4-yl)-2-(Z)-(methoxyimino) acetamido]-3-cephem-4-carboxylate sodium salt (I) with 4-(5-oxazolyl)pyridine by means of NaI and HCl in hot acetonitrile. The title product has been obtained in high purity by passing its NaOH solution, adjusted at pH 6.8, through a column packed with Diaion PA 406. The eluate is concentrated and acidified at pH 1.5 with H2SO4. After cooling, the H2SO4 salt of the title product is obtained with a 99.8% purity. Another purification method is to pass the NaOH solution through a Cl-form Diaion PA 406 column. The eluate is then subjected to reverse osmosis on a RS-9267 membrane to eliminate the NaCl (final purity 99.2%). The synthesis of 7-amino-3-[4-(oxazol-5-yl)-1-pyridinio]methyl-3-cephem-4-carboxylate borofluorate as an intermediate in the synthesis of title compound has been reported. The enzyme pancreatine has been used to protect and deprotect the 7-amino group of cephalosporin.

参考文献No.18898
标题:Process for the preparation of a high purity cephalosporin deriv
作者:Ikumoto, Y.; Kanauchi, T. (Daiichi Pharmaceutical Co., Ltd.)
来源:JP 1990172989
合成路线图解说明:

By condensation of 3-(acetoxymethyl)-7-[2-(2-aminothiazol-4-yl)-2-(Z)-(methoxyimino) acetamido]-3-cephem-4-carboxylate sodium salt (I) with 4-(5-oxazolyl)pyridine by means of NaI and HCl in hot acetonitrile. The title product has been obtained in high purity by passing its NaOH solution, adjusted at pH 6.8, through a column packed with Diaion PA 406. The eluate is concentrated and acidified at pH 1.5 with H2SO4. After cooling, the H2SO4 salt of the title product is obtained with a 99.8% purity. Another purification method is to pass the NaOH solution through a Cl-form Diaion PA 406 column. The eluate is then subjected to reverse osmosis on a RS-9267 membrane to eliminate the NaCl (final purity 99.2%). The synthesis of 7-amino-3-[4-(oxazol-5-yl)-1-pyridinio]methyl-3-cephem-4-carboxylate borofluorate as an intermediate in the synthesis of title compound has been reported. The enzyme pancreatine has been used to protect and deprotect the 7-amino group of cephalosporin.

参考文献No.18899
标题:Process for the preparation of a cephem antibiotic
作者:Shimizu, S.; Suda, Y.; Kanauchi, T. (Daiichi Pharmaceutical Co., Ltd.)
来源:JP 1990188586
合成路线图解说明:

By condensation of 3-(acetoxymethyl)-7-[2-(2-aminothiazol-4-yl)-2-(Z)-(methoxyimino) acetamido]-3-cephem-4-carboxylate sodium salt (I) with 4-(5-oxazolyl)pyridine by means of NaI and HCl in hot acetonitrile. The title product has been obtained in high purity by passing its NaOH solution, adjusted at pH 6.8, through a column packed with Diaion PA 406. The eluate is concentrated and acidified at pH 1.5 with H2SO4. After cooling, the H2SO4 salt of the title product is obtained with a 99.8% purity. Another purification method is to pass the NaOH solution through a Cl-form Diaion PA 406 column. The eluate is then subjected to reverse osmosis on a RS-9267 membrane to eliminate the NaCl (final purity 99.2%). The synthesis of 7-amino-3-[4-(oxazol-5-yl)-1-pyridinio]methyl-3-cephem-4-carboxylate borofluorate as an intermediate in the synthesis of title compound has been reported. The enzyme pancreatine has been used to protect and deprotect the 7-amino group of cephalosporin.

参考文献No.145416
标题:DQ-2556
作者:Prous, J.; Casta馿r, J.
来源:Drugs Fut 1991,16(8),709
合成路线图解说明:

By condensation of 3-(acetoxymethyl)-7-[2-(2-aminothiazol-4-yl)-2-(Z)-(methoxyimino) acetamido]-3-cephem-4-carboxylate sodium salt (I) with 4-(5-oxazolyl)pyridine by means of NaI and HCl in hot acetonitrile. The title product has been obtained in high purity by passing its NaOH solution, adjusted at pH 6.8, through a column packed with Diaion PA 406. The eluate is concentrated and acidified at pH 1.5 with H2SO4. After cooling, the H2SO4 salt of the title product is obtained with a 99.8% purity. Another purification method is to pass the NaOH solution through a Cl-form Diaion PA 406 column. The eluate is then subjected to reverse osmosis on a RS-9267 membrane to eliminate the NaCl (final purity 99.2%). The synthesis of 7-amino-3-[4-(oxazol-5-yl)-1-pyridinio]methyl-3-cephem-4-carboxylate borofluorate as an intermediate in the synthesis of title compound has been reported. The enzyme pancreatine has been used to protect and deprotect the 7-amino group of cephalosporin.

参考文献No.145439
标题:Synthesis and antimicrobial activity of cephalosporins with a 1-pyridinium substituent carrying a 5-membered heterocycle at the C-3 position
作者:Ejima, A.; Hayano, T.; Ebata, T.; Nagahara, T.; Koda, H.; Tagawa, H.; Furukawa, M.
来源:J Antibiot 1987,40(1),43-8
合成路线图解说明:

By condensation of 3-(acetoxymethyl)-7-[2-(2-aminothiazol-4-yl)-2-(Z)-(methoxyimino) acetamido]-3-cephem-4-carboxylate sodium salt (I) with 4-(5-oxazolyl)pyridine by means of NaI and HCl in hot acetonitrile. The title product has been obtained in high purity by passing its NaOH solution, adjusted at pH 6.8, through a column packed with Diaion PA 406. The eluate is concentrated and acidified at pH 1.5 with H2SO4. After cooling, the H2SO4 salt of the title product is obtained with a 99.8% purity. Another purification method is to pass the NaOH solution through a Cl-form Diaion PA 406 column. The eluate is then subjected to reverse osmosis on a RS-9267 membrane to eliminate the NaCl (final purity 99.2%). The synthesis of 7-amino-3-[4-(oxazol-5-yl)-1-pyridinio]methyl-3-cephem-4-carboxylate borofluorate as an intermediate in the synthesis of title compound has been reported. The enzyme pancreatine has been used to protect and deprotect the 7-amino group of cephalosporin.

参考文献No.157715
标题:A synthetic method of 3-quarternary ammonium derivatives from 7-ACA utilizing enzymatic reactions
作者:Nishio, H.; Miyatera, A.
来源:111th Annu Meet Pharmaceut Soc Jpn (March 28-30, Tokyo) 1991,Abst 29 TL 1-005.
合成路线图解说明:

By condensation of 3-(acetoxymethyl)-7-[2-(2-aminothiazol-4-yl)-2-(Z)-(methoxyimino) acetamido]-3-cephem-4-carboxylate sodium salt (I) with 4-(5-oxazolyl)pyridine by means of NaI and HCl in hot acetonitrile. The title product has been obtained in high purity by passing its NaOH solution, adjusted at pH 6.8, through a column packed with Diaion PA 406. The eluate is concentrated and acidified at pH 1.5 with H2SO4. After cooling, the H2SO4 salt of the title product is obtained with a 99.8% purity. Another purification method is to pass the NaOH solution through a Cl-form Diaion PA 406 column. The eluate is then subjected to reverse osmosis on a RS-9267 membrane to eliminate the NaCl (final purity 99.2%). The synthesis of 7-amino-3-[4-(oxazol-5-yl)-1-pyridinio]methyl-3-cephem-4-carboxylate borofluorate as an intermediate in the synthesis of title compound has been reported. The enzyme pancreatine has been used to protect and deprotect the 7-amino group of cephalosporin.

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