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【结 构 式】 
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【药物名称】 【化学名称】2-[3-[5-Methyl-2-[4-(trifluoromethoxy)phenyl]oxazol-4-ylmethoxy]benzyl]-1,2,4-oxadiazolidine-3,5-dione 【CA登记号】174727-56-1 【 分 子 式 】C21H16F3N3O6 【 分 子 量 】463.37337 |
【开发单位】Amgen (Originator), Wyeth Pharmaceuticals (Originator) 【药理作用】Antidiabetic Drugs, ENDOCRINE DRUGS, Type 2 Diabetes Mellitus, Agents for |
合成路线1
Condensation of the (chloromethyl)oxazole (I) with 3-hydroxybenzaldehyde (II) in the presence of K2CO3 afforded ether (III). The aldehyde group of (III) was then converted to oxime (IV) upon treatment with hydroxylamine hydrochloride and sodium acetate. Reduction of oxime (IV) with NaBH3CN produced the hydroxylamine (V). This was finally condensed with N-(chlorocarbonyl)isocyanate to produce the target oxadiazolidine dione.
| 【1】 Malamas, M.S.; et al.; Antihyperglycemic activity of new 1,2,4-oxadiazolidine-3,5-diones. Eur J Med Chem 2001, 36, 1, 31. |
| 【2】 Malamas, M.S.; Palka, C.L.; Gunawan, I. (American Home Products Corp.); Aralkyl-1,2,4-oxadiazolidine-3,5-diones as antihyperglycemic agents. US 5480896 . |
| 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) | 49144 | 4-(chloromethyl)-5-methyl-2-[4-(trifluoromethoxy)phenyl]-1,3-oxazole; 4-[4-(chloromethyl)-5-methyl-1,3-oxazol-2-yl]phenyl trifluoromethyl ether | C12H9ClF3NO2 | 详情 | 详情 | |
| (II) | 28537 | 3-hydroxybenzaldehyde | 100-83-4 | C7H6O2 | 详情 | 详情 |
| (III) | 49145 | 3-([5-methyl-2-[4-(trifluoromethoxy)phenyl]-1,3-oxazol-4-yl]methoxy)benzaldehyde | C19H14F3NO4 | 详情 | 详情 | |
| (IV) | 49146 | 3-([5-methyl-2-[4-(trifluoromethoxy)phenyl]-1,3-oxazol-4-yl]methoxy)benzaldehyde oxime | C19H15F3N2O4 | 详情 | 详情 | |
| (V) | 49147 | N-[3-([5-methyl-2-[4-(trifluoromethoxy)phenyl]-1,3-oxazol-4-yl]methoxy)benzyl]hydroxylamine; 4-([3-[(hydroxyamino)methyl]phenoxy]methyl)-5-methyl-2-[4-(trifluoromethoxy)phenyl]-1,3-oxazole | C19H17F3N2O4 | 详情 | 详情 |
Extended Information