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【结 构 式】 
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【药物名称】Adatanserin hydrochloride, WAY-SEB-324, SEB-324, Wy-50324 【化学名称】N-[2-[4-(2-Pyrimidinyl)piperazin-1-yl]ethyl]adamantane-1-carboxamide hydrochloride 【CA登记号】127266-75-5 (diHCl), 127266-56-2 (free base), 144966-96-1 (monoHCl) 【 分 子 式 】C21H32ClN5O 【 分 子 量 】405.97509 |
【开发单位】Wyeth Pharmaceuticals (Originator) 【药理作用】Antidepressants, Anxiolytics, Mood Disorders, Treatment of, PSYCHOPHARMACOLOGIC DRUGS, 5-HT1A Receptor Agonists, 5-HT2A Antagonists |
合成路线1
Adamantane-1-carboxylic acid chloride (freshly prepared from the reaction of thionyl chloride (I) with the adamantane-1-carboxylic acid) was reacted with 1-(2-aminoethyl)-4-(2-pyrimidinyl)piperazine (II) in CH2Cl2 in the presence of triethylamine (TEA) to afford Wy-50,324 free base in 70% (III) yield which was converted to the hydrochloride salt using ethanolic HCl solution.
| 【1】 Abou-Gharbia, M.A.; et al.; Synthesis and SAR of adatanserin: Novel adamantyl aryl- and heteroarylpiperazines with dual serotonin 5-HT1A and activity as potential anxiolytic and antidepressant agents. J Med Chem 1999, 42, 25, 5077. |
| 【2】 Abou-Gharbia, M.A.-M.; Yardley, J.P.; Childers, W.E. Jr. (American Home Products Corp.); Aryl- and heteroaryl piperazinyl carboxamides having CNS activity. AU 8935025; EP 0343961; JP 1990015059 . |
| 【3】 Abou-Gharbia, M.; Moyer, J.A.; Wy-50,324. Drugs Fut 1990, 15, 11, 1093. |
| 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) | 31216 | 1-adamantanecarbonyl chloride | 2094-72-6 | C11H15ClO | 详情 | 详情 |
| (II) | 31217 | 2-[4-(2-pyrimidinyl)-1-piperazinyl]ethylamine; 2-[4-(2-pyrimidinyl)-1-piperazinyl]-1-ethanamine | C10H17N5 | 详情 | 详情 | |
| (III) | 31218 | N-[2-[4-(2-pyrimidinyl)-1-piperazinyl]ethyl]-1-adamantanecarboxamide | C21H31N5O | 详情 | 详情 |