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【结 构 式】 
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【药物名称】M-12325 【化学名称】2,4-Dichloro-5-sulfamoylbenzoic acid sodium salt 【CA登记号】2736-23-4 (free acid) 【 分 子 式 】C7H4Cl2NNaO4S 【 分 子 量 】292.07403 |
【开发单位】Mochida (Originator) 【药理作用】ANTIINFECTIVE THERAPY, Antiviral Drugs |
合成路线1
The sulfonation of 2,4-dichlorobenzoic acid (I) with chlorosulfonic acid (II) at 140 C gives 5-chlorosulfonyl-2,4-dichlorobenzoic acid (III), which by reaction with liquid NH3 is converted into 5-sulfamoyl-2,4-dichlorobenzoic acid (IV). Finally, this compound is treated with NaOH.
| 【1】 Flueckiger, E.; Lindenmann, A.; Taeschler, M.; Schenker, E.; Jucker, E.; Synthetic drugs, XII. Constitution and salidiuretic effect of 3-sulfamoyl-4-chlorobenzoic acid derivatives and related compounds. Arzneim-Forsch Drug Res 1963, 13, 4, 269-280. |
| 【2】 Stephenson, O.; Wild, A.M.; Petrow, V.; Jackman, G.B.; Diuretic agents. VI. Some sulfamoylbenzoic acids. J Pharm Pharmacol 1962, 14, 679-686. |
| 【3】 Rusching, H.; Siedel, W.; Sturm, K.; Weyer, R.; Chemistry of furosemide. I. Syntheses of 5-sulfamoylanthranilic acid derivatives. Chem Ber 1966, 99, 1, 328-344. |
| 【4】 Hopkins, S.J.; Castaner, J.; Serradell, M.N.; Blancafort, P.; M-12,325. Drugs Fut 1983, 8, 3, 206. |
| 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) | 33443 | 2,4-dichlorobenzoic carboxylic acid; 2,4-dichlorobenzoic acid | 50-84-0 | C7H4Cl2O2 | 详情 | 详情 |
| (II) | 35975 | 2,4-dichloro-5-(chlorosulfonyl)benzoic acid | C7H3Cl3O4S | 详情 | 详情 | |
| (III) | 35976 | 5-(aminosulfonyl)-2,4-dichlorobenzoic acid; 2,4-Dichloro-5-sulfamoylbenzoic acid; lassamide | 2736-23-4 | C7H5Cl2NO4S | 详情 | 详情 |
Extended Information