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【结 构 式】 
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【药物名称】Lerisetron, F-0930-RS 【化学名称】1-Benzyl-2-(1-piperazinyl)benzimidazole 【CA登记号】143257-98-1 【 分 子 式 】C18H20N4 【 分 子 量 】292.3869 |
【开发单位】FAES (Originator), PharmaMar (Licensee) 【药理作用】Nausea and Vomiting, Treatment of, NEUROLOGIC DRUGS, 5-HT3 Antagonists |
合成路线1
N-Alkylation of 2-chlorobenzimidazole (I) with benzyl bromide (II) by means of NaH in DMF provides benzylated derivative (III), which is converted into the desired compound by heating with piperazine (IV).
| 【1】 Parihar, H.S.; et al.; 5-HT3R binding of lerisetron: An interdisciplinary approach to drug-receptor interactions. Bioorg Med Chem Lett 2001, 11, 16, 2133. |
| 【2】 Orjales, A.; et al.; New 2-piperazinylbenzimidazole derivatives as 5-HT3 antagonists. Synthesis and pharmacological evaluation. J Med Chem 1997, 40, 4, 586. |
| 【3】 Orjales-Venero, A.; Garcia-Dominguez, N.; Rubio-Royo, V.; Rodes-Solanes, R. (FAES); New 2-piperazinylbenzimidazole derivs.. EP 0512939; JP 1995002795; US 5256665 . |
| 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) | 26761 | 2-chloroimidazo[1,2-a]pyridine; 2-chlorobenzimidazole; 2-Amino-4'-chlorodiphenylether; 2-Aminodiphenylether; 2-chloro-1H-benzimidazole | 4857-06-1 | C7H5ClN2 | 详情 | 详情 |
| (II) | 12912 | 1-(Bromomethyl)benzene; Alpha-bromotoluene | 100-39-0 | C7H7Br | 详情 | 详情 |
| (III) | 49687 | 1-Benzyl-2-chloro-1H-benzoimidazole | C14H11ClN2 | 详情 | 详情 | |
| (IV) | 10355 | Diethylenediamine; Piperazine | 110-85-0 | C4H10N2 | 详情 | 详情 |
Extended Information