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【结 构 式】 
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【药物名称】Compound 301029, 301029 【化学名称】N-(5-Phenyl-1,2,4-thiadiazol-3-yl)thiourea 【CA登记号】97149-60-5 【 分 子 式 】C9H8N4S2 【 分 子 量 】236.31891 |
【开发单位】Procter & Gamble (Originator) 【药理作用】ANTIINFECTIVE THERAPY, Antiviral Drugs |
合成路线1
Condensation of benzoyl chloride (I) with ammonium thiocyanate in boiling acetone produces benzoyl isothiocyanate (II). This is then coupled with the known 3-amino-5-phenyl-1,2,4-thiadiazole (III) to afford the N-benzoyl thiourea (IV) (1). Finally, hydrolysis of (IV) under alkaline conditions gives rise to the target thiadiazolyl thiourea
| 【1】 Kurzer, F.; 1,2,4-Thiadiazolylureas. A postcript to the oxidative cyclisation of thionoamidines. J Chem Soc - Perkins Trans I 1985, 2, 311. |
| 【2】 Camden, J.B. (The Procter & Gamble Co.); Thiadiazolyl urea or thiourea derivs. for antiviral treatment. JP 2002540156; US 6258831; WO 0057878 . |
| 【3】 Agyin, J.K. (The Procter & Gamble Co.); Process for the preparation of 1,2,4-thiadiazoles. US 6297384 . |
| 【4】 Camden, J.B. (The Procter & Gamble Co.); Viral treatment. JP 2002540150; US 6245788; WO 0057869 . |
| 【5】 Camden, J.B. (The Procter & Gamble Co.); Viral treatment. US 6340696 . |
合成路线2
In a similar method, 3-amino-5-phenyl-1,2,4-tiadiazole (I) is coupled with ethoxycarbonyl isothiocyanate to give the N-(ethoxycarbonyl)thiourea (II), which is then hydrolyzed to the title compound under alkaline conditions
| 【1】 Kurzer, F.; Secker, J.L.; Addition-cyclisations of ethoxycarbonyl isothiocyanate with hydrazine derivatives as a source of thiadiazoles and triazoles. J Heterocycl Chem 1989, 26, 2, 355. |