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【结 构 式】 
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【药物名称】Sulcephalosporin, Cefsulodin sodium, SCE-129, CGP-7174/E, Abbott-46811, Tilmapor, Takesulin, Pseudomonil, Pseudocef, Monaspor 【化学名称】4-Carbamoyl-1-[[(6R,7R)-2-carboxy-8-oxo-7-[(2R)-2-phenyl-2-sulfoacetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]pyridinium hydroxide,inner salt,sodium salt 【CA登记号】52152-93-9, 62587-73-9 (free acid) 【 分 子 式 】C22H19N4NaO8S2 【 分 子 量 】554.53653 |
【开发单位】Novartis (Originator), Takeda (Originator) 【药理作用】Antibiotics, ANTIINFECTIVE THERAPY, Cephalosporins |
合成路线1
The reaction of 7-aminocephalosporanic acid (I) with alpha-sulfophenylacetyl chloride (II) by means of NaOH and NaHCO3 in ether gives 7-(alpha-sulfophenylacetamido)cephalosporanic acid (III), which is then condensed with isonicotinamide (IV) by means of KSCN and pyridine in water.
| 【1】 Nomura, H.; et al.; Semisynthetic beta-lactams antibiotics. VII. New semisynthetic cephalosporins derived from alpha-sulfophenylacetic acid. Heterocycles 1974, 2, 1, 67-72. |
| 【2】 Morimoto, S.; et al.; Cephalosporin compounds. DE 2234280; ES 404745; FR 2146313; NL 7209811 . |
| 【3】 Nomura, H.; et al.; Semisynthetic beta-lactam antibiotics. 6. Sulfocephalosporins and their antipseudomonal activities. J Med Chem 1974, 17, 12, 1312-15. |
| 【4】 Blancafort, P.; Castaner, J.; Serradell, M.N.; Sweetman, A.J.; Cefsulodin. Drugs Fut 1980, 5, 2, 67. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 22747 | (6R,7R)-3-[(acetoxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid | C10H12N2O5S | 详情 | 详情 | |
| (II) | 32665 | (1S)-2-chloro-2-oxo-1-phenyl-1-ethanesulfonic acid | C8H7ClO4S | 详情 | 详情 | |
| (III) | 32666 | (6R,7R)-3-[(acetoxy)methyl]-8-oxo-7-[[(2S)-2-phenyl-2-sulfoethanoyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid | C18H18N2O9S2 | 详情 | 详情 | |
| (IV) | 25191 | isonicotinamide | 1453-82-3 | C6H6N2O | 详情 | 详情 |