|
【结 构 式】 
|
【药物名称】Imiloxan, RS-21361 【化学名称】(±)-2-[(2,3-Dihydro-1,4-benzodioxin-2-yl)methyl]-1-ethyl-1H-imidazole 【CA登记号】81167-16-0, 86710-23-8 (HCl), 81167-22-8 (monoHCl) 【 分 子 式 】C14H16N2O2 【 分 子 量 】244.29582 |
【开发单位】Roche Bioscience (Originator) 【药理作用】Antidepressants, Mood Disorders, Treatment of, PSYCHOPHARMACOLOGIC DRUGS, alpha2-Adrenoceptor Antagonists |
合成路线1
The partial alcoholysis of 2-cyanomethyl-1,4-benzodioxane (I) with ethanol and HCl in ether gives ethyl-(1,4-benzodioxan-2-yl)acetimidate (II), which is cyclized with aminoacetaldehyde diethylketal (III) in refluxing ethanol yielding 2-[(1,4-benzodioxan-2-yl)methyl]imidazole (IV). Finally, this compound is alkylated with ethyl iodide (V) and NaH in DMF.
| 【1】 Caroon, J.M.; et al.; Structure-activity relationships for 2-substituted imidazoles as alpha2-adrenoceptor antagonists. J Med Chem 1982, 25, 6, 666-670. |
| 【2】 Kluge, A.F.; Strosberg, A.M.; Whiting, R.; Christie, G. (Syntex (USA), Inc.); 2-(1,4-Benzodioxan-2-ylalkyl)miidazoles useful as antidepressants. EP 0047531; JP 57050989; US 4302469 . |
| 【3】 Castaner, J.; Serradell, M.N.; Imiloxan. Drugs Fut 1986, 11, 2, 108. |
| 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) | 28755 | 2-(2,3-dihydro-1,4-benzodioxin-2-yl)acetonitrile | C10H9NO2 | 详情 | 详情 | |
| (II) | 28756 | ethyl 2-(2,3-dihydro-1,4-benzodioxin-2-yl)ethanimidoate | C12H15NO3 | 详情 | 详情 | |
| (III) | 10331 | 2,2-Diethoxy-1-ethanamine; 2,2-Diethoxyethylamine; Aminoacetaldehyde diethyl acetal | 645-36-3 | C6H15NO2 | 详情 | 详情 |
| (IV) | 28757 | 2-(2,3-dihydro-1,4-benzodioxin-2-ylmethyl)-1H-imidazole | C12H12N2O2 | 详情 | 详情 | |
| (V) | 28758 | 1-iodopropane | 107-08-4 | C3H7I | 详情 | 详情 |