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【结 构 式】 
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【药物名称】Cefuzonam sodium, CL-118523(free acid), LJC-10305, L-105, MTC.Na, CL-251931(free acid), Cosmosin 【化学名称】(6R,7R)-7beta-[2-(2-Aminothiazol-4-yl)-2(Z)-(methoxyimino)acetamido]-3-(1,2,3-thiadiazol-5-ylsulfanylmethyl)-3-cephem-4-carboxylic acid sodium salt 【CA登记号】82219-78-1 (free acid) 【 分 子 式 】C16H14N7NaO5S4 【 分 子 量 】535.57968 |
【开发单位】Takeda (Originator), Wyeth Pharmaceuticals (Originator) 【药理作用】Cephalosporins |
合成路线1
The condensation of 7-aminocephalosporanic acid (I) with sodium 1,2,3-thiadiazole-5-thiolate (II) gives 7-amino-3-[1,2,3-thiadiazol-5-ylmethyl]-3-cephem-4-carboxylic acid (III). Following the first step, condensation of (III) with 2-(2-chloroacetamidothiazol-4-yl)-sulfanyl-(Z)-2-methoxyiminoacetyl chloride hydrochloride (IV) followed by deprotection with sodium N-methyldithiocarbamate (V) affords sodium 7-[(Z)-2-(2-aminothiazol-4yl)-2-(methoxyimino)acetamido)-3-(1,2,3-thiadiazol-5-ylsulfanylmethyl)-3-cephem-4-carboxylate.
| 【1】 Bietti, G.; Cereda, E.; Donetti, A.; Giachetti, A.; Pagani, F. (Angelini Inst SpA); Antiulcerogenic amidine derivatives of 2-substituted 4-phenylimidazole.. EP 0131973; GB 2149395; US 4649150 . |
| 【2】 Scarpignato, C.; Bisfentidine. Drugs Fut 1988, 13, 2, 110. |
| 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) | 22748 | 1,2,3-thiadiazol-5-thiol sodium salt | C2HN2NaS2 | 详情 | 详情 | |
| (III) | 22749 | (6R,7R)-7-amino-8-oxo-3-[(1,2,3-thiadiazol-5-ylsulfanyl)methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid | C10H10N4O3S3 | 详情 | 详情 | |
| (IV) | 22750 | 2-[2-[(2-chloroacetyl)amino]-1,3-thiazol-5-yl]-2-(methoxyimino)acetyl chloride | C8H7Cl2N3O3S | 详情 | 详情 | |
| (V) | 22751 | N-Methyldithiocarbamic acid sodium salt | C2H4NNaS2 | 详情 | 详情 |