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项目整合精选>>>Ceftriaxone sodium, Ro-139904, Lendacin, Rocefalin, Rocephalin, Rocefin, Longaceph, Rocephine, Rocephin
Ceftriaxone sodium, Ro-139904, Lendacin, Rocefalin, Rocephalin, Rocefin, Longaceph, Rocephine, Rocephin
头孢曲松钠 头孢曲松 Chemical Name: (6R,7R)-7-[2-(2-Amino-4-thiazolyl)-2[(Z)-methoxyimino]acetamido]-3-[[(2,5-dihydro-6-hydroxy-2-methyl-5-oxo-as-triazin-3-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid disodium salt; (6R,7R)-7-[2-(2-Amino-4-thiazolyl)glyoxylamido]-3-[[(2,5-dihydro-6-hydroxy-2-methyl-5-oxo-as-triazin-3-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid 7(2)-(Z)-(O)-methyloxime) disodium salt
CAS No. 74578-69-1, 73384-59-5 (free acid)
项目整合开发状态: Launched-1982
项目研究机构: Chugai (Originator), Roche (Originator), Cubist (Licensee), Egis (Licensee), Valeant (Licensee)
合成路线:The reaction of methylhydrazin (I) with potassium thiocyanate (II) gives N-methyl-N-aminothiourea (III),which is cyclized with dimethyl oxalate (IV) by means of sodium methoxide in methanol to afford 2,5-dihydro-6-hydroxy-2-methyl-3-mercapto-5-oxo-1,2,4-triazine (V).The reaction of (V) with 7-aminocephalosporanic acid (VI) in a buffer solution at pH 6.5 gives 7-amino-3,4-[(2,5-dihydro-6-hydroxy-2-methyl-5-oxo-as-triazin-3-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (VII),which is condensed with 2-(2-chloroacetamido-4-thiazolyl)-2-[(Z)-methoxyimino]acetyl chloride (VIII) at pH 2 yielding 7-]2-(2-chloroacetamido-4-thiazolyl)-2-[(Z)-methoxyimino]acetamido-3-[[(2,5-dihydro-6-hydroxy-2-methyl-5-oxo-as-triazin-3-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (IX).Finally,this compound is hydrolyzed and treated with sodium hydroxide.
📌 参考资料/链接：
参考文献标题:Cephalosporin derivs.and process for their preparation
文献作者:Reiner,R.; Montavon,M.(F.Hoffmann-La Roche AG)
参考来源:DE 2922036
📄 详细内容
合成路线:The reaction of methylhydrazin (I) with potassium thiocyanate (II) gives N-methyl-N-aminothiourea (III),which is cyclized with dimethyl oxalate (IV) by means of sodium methoxide in methanol to afford 2,5-dihydro-6-hydroxy-2-methyl-3-mercapto-5-oxo-1,2,4-triazine (V).The reaction of (V) with 7-aminocephalosporanic acid (VI) in a buffer solution at pH 6.5 gives 7-amino-3,4-[(2,5-dihydro-6-hydroxy-2-methyl-5-oxo-as-triazin-3-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (VII),which is condensed with 2-(2-chloroacetamido-4-thiazolyl)-2-[(Z)-methoxyimino]acetyl chloride (VIII) at pH 2 yielding 7-]2-(2-chloroacetamido-4-thiazolyl)-2-[(Z)-methoxyimino]acetamido-3-[[(2,5-dihydro-6-hydroxy-2-methyl-5-oxo-as-triazin-3-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (IX).Finally,this compound is hydrolyzed and treated with sodium hydroxide.
参考文献标题:Ro-13-9904/001,a novel potent and long-acting parenteral cephalosporin
文献作者:Reiner,R.; Weiss,U.; Brombacher,U.; Lanz,P.; Montavon,M.; Furlenmeier,A.; Angehrn,P.; Probst,P.J.
参考来源:J Antibiot 1980,32(7),783-786
合成路线:The reaction of methylhydrazin (I) with potassium thiocyanate (II) gives N-methyl-N-aminothiourea (III),which is cyclized with dimethyl oxalate (IV) by means of sodium methoxide in methanol to afford 2,5-dihydro-6-hydroxy-2-methyl-3-mercapto-5-oxo-1,2,4-triazine (V).The reaction of (V) with 7-aminocephalosporanic acid (VI) in a buffer solution at pH 6.5 gives 7-amino-3,4-[(2,5-dihydro-6-hydroxy-2-methyl-5-oxo-as-triazin-3-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (VII),which is condensed with 2-(2-chloroacetamido-4-thiazolyl)-2-[(Z)-methoxyimino]acetyl chloride (VIII) at pH 2 yielding 7-]2-(2-chloroacetamido-4-thiazolyl)-2-[(Z)-methoxyimino]acetamido-3-[[(2,5-dihydro-6-hydroxy-2-methyl-5-oxo-as-triazin-3-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (IX).Finally,this compound is hydrolyzed and treated with sodium hydroxide.
参考文献标题:Cefatriaxon
文献作者:Neuman,M.
参考来源:Drugs Fut 1981,6(3),132
产品链接: CAS No. 74578-69-1›› 产品链接: CAS No.73384-59-5››