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【结 构 式】 
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【药物名称】 【化学名称】N-Methyl-3-(pentafluorophenyl)-2(S)-[3-(5-thioxo-4,5-dihydro-1,3,4-thiadiazol-2-yl)ureido]propionamide 【CA登记号】 【 分 子 式 】C13H10F5N5O2S2 【 分 子 量 】427.37695 |
【开发单位】Pfizer (Originator) 【药理作用】Antiarthritic Drugs, TREATMENT OF MUSCULOSKELETAL & CONNECTIVE TISSUE DISEASES, Matrix Metalloproteinase Inhibitors |
合成路线1
Pentafluorophenylalanine methyl ester (I) was treated with phosgene and pyridine to afford isocyanate (II), which was condensed with 5-aminothiadiazole-2-thione (III) to provide urea (IV). Then, displacement of the ester function of (IV) with methylamine furnished the title amide.
| 【1】 Mitchell, M.A.; Hendges, S.K.; Jacobsen, E.J.; et al.; Synthesis of a series of stromelysin-selective thiadiazole urea matrix metalloproteinase inhibitors. J Med Chem 1999, 42, 9, 1525. |
| 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) | 24395 | methyl (2S)-2-amino-3-(2,3,4,5,6-pentafluorophenyl)propanoate | C10H8F5NO2 | 详情 | 详情 | |
| (II) | 24396 | methyl (2S)-2-isocyanato-3-(2,3,4,5,6-pentafluorophenyl)propanoate | C11H6F5NO3 | 详情 | 详情 | |
| (III) | 24397 | 5-amino-1,3,4-thiadiazole-2(3H)-thione | 2349-67-9 | C2H3N3S2 | 详情 | 详情 |
| (IV) | 24398 | methyl (2S)-3-(2,3,4,5,6-pentafluorophenyl)-2-([[(5-thioxo-4,5-dihydro-1,3,4-thiadiazol-2-yl)amino]carbonyl]amino)propanoate | C13H9F5N4O3S2 | 详情 | 详情 |
Extended Information