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【结 构 式】 
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【药物名称】Irtemazole, R-60844 【化学名称】(±)-5-[alpha-(1H-Imidazol-1-yl)benzyl]-2-methyl-1H-benzimidazole 【CA登记号】115574-30-6 【 分 子 式 】C18H16N4 【 分 子 量 】288.35502 |
【开发单位】Janssen (Originator) 【药理作用】METABOLIC DRUGS, Treatment of Disorders of Purine and Pyrimidine Metabolism, Treatment of Gout, Uricosurics |
合成路线1
The cyclization of 3,4-diaminobenzophenone (I) with acetylimidic acid ethyl ester (II) in refluxing methanol gives 5-benzoyl-2-methylbenzimidazole (III), which is reduced with NaBH4 in methanol yielding 5-(alpha-hydroxybenzyl)-2-methylbenzimidazole (IV). Finally, this compound is condensed with imidazole (V) in refluxing acetonitrile.
| 【1】 Raeymaekers, A.H.M.; Freyne, E.J.E.; Sanz, G.C. (Janssen Pharmaceutica NV); Novel (1H-imidazol-1-ylmethyl) substd. benzimidazole derivs. AU 8778385; EP 0260744; JP 1989085975; US 4859684 . |
| 【2】 Castaner, J.; Prous, J.; Irtemazole. Drugs Fut 1991, 16, 12, 1094. |
| 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) | 12830 | (3,4-Diaminophenyl)phenylmethanone; 3,4-Diaminobenzophenone | 39070-63-8 | C13H12N2O | 详情 | 详情 |
| (II) | 12831 | ethyl ethanimidoate | 1000-84-6 | C4H9NO | 详情 | 详情 |
| (III) | 12832 | (2-Methyl-1H-benzimidazol-5-yl)(phenyl)methanone | C15H12N2O | 详情 | 详情 | |
| (IV) | 12833 | (2-Methyl-1H-benzimidazol-5-yl)(phenyl)methanol | C15H14N2O | 详情 | 详情 | |
| (V) | 10255 | Imidazole; 1H-Imidazole | 288-32-4 | C3H4N2 | 详情 | 详情 |
Extended Information