DQ-2556

Chemical Name: (6R,7R)-7-[2-(2-Aminothiazol-4-yl)-2(Z)-(methoxyimino)acetamido]-3-[4-(5-oxazolyl)pyridinio-1-ylmethyl]-3-cephem-4-carboxylate; [6R-[6alpha,7beta(Z)]]-1-[[7-[[(2-Amino-4-thiazolyl)(methoxyimino)acetyl]amino]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-4-(5-oxazolyl)pyridinium hydroxide inner salt
CAS No. 102253-70-3
项目整合开发状态: Phase II
项目研究机构: Daiichi Pharmaceutical (Originator)
合成路线: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.
📌 参考资料/链接:
参考文献标题:Cephalosporin derivs.,process for preparing them and pharmaceutical compsns.containing them
文献作者:Furukawa,M.; Tagawa,H.; Hayano,T.; Ejima,A.(Daiichi Pharmaceutical Co.,Ltd.)
参考来源:AU 8541333; EP 0159011; ES 8607319; JP 1985222490; JP 1986007280

📄 详细内容


合成路线: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.

参考文献标题:Process for the preparation of a high purity cephalosporin deriv
文献作者:Ikumoto,Y.; Kanauchi,T.(Daiichi Pharmaceutical Co.,Ltd.)
参考来源:JP 1990172989


合成路线: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.

参考文献标题:Process for the preparation of a cephem antibiotic
文献作者:Shimizu,S.; Suda,Y.; Kanauchi,T.(Daiichi Pharmaceutical Co.,Ltd.)
参考来源:JP 1990188586


合成路线: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.

参考文献标题:DQ-2556
文献作者:Prous,J.; Castar,J.
参考来源:Drugs Fut 1991,16(8),709


合成路线: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.

参考文献标题:Synthesis and antimicrobial activity of cephalosporins with a 1-pyridinium substituent carrying a 5-membered heterocycle at the C-3 position
文献作者:Ejima,A.; Hayano,T.; Ebata,T.; Nagahara,T.; Koda,H.; Tagawa,H.; Furukawa,M.
参考来源:J Antibiot 1987,40(1),43-8


合成路线: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.
参考文献标题:A synthetic method of 3-quarternary ammonium derivatives from 7-ACA utilizing enzymatic reactions
文献作者:Nishio,H.; Miyatera,A.
参考来源:111th Annu Meet Pharmaceut Soc Jpn (March 28-30,Tokyo) 1991,Abst 29 TL 1-005.


产品链接: CAS No. 102253-70-3››