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【结 构 式】 
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【药物名称】Gevotroline hydrochloride, Wy-47384 【化学名称】8-Fluoro-2-[3-(3-pyridinyl)propyl]-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole hydrochloride 【CA登记号】107266-18-2 (diHCl), 107266-06-8 (free base), 112243-58-0 (monoHCl) 【 分 子 式 】C19H20FN3 【 分 子 量 】309.38975 |
【开发单位】Wyeth Pharmaceuticals (Originator) 【药理作用】Antipsychotic Drugs, PSYCHOPHARMACOLOGIC DRUGS |
合成路线1
The reaction of 4-fluorophenylhydrazine hydrochloride (I) with N-carbethoxy-4-piperidone (II) under Fisher's conditions affords N2-carbethoxy-8-fluoro-2,3,4,5-tetrahydro-1H-pyridol[4,3-b]indole (III). Treatment of (III) with Claisen's alkali affords the N-2 unsubstituted 8-fluoro-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (IV), which is finally condensed with 3-pyridinylpropyl bromide hydrobromide (V) in DMF in the presence of triethyl amine (TEA). Compound (V) is obtained by refluxing 3-pyridinylpropanol with 48% hydrobromic acid.
| 【1】 Andree, T.H.; Webb, M.B.; Patel, U.R.; Muth, E.A.; Moyer, J.A.; Abou-Gharbia, M.; Antipsychotic activity of substituted gamma-carbol. J Med Chem 1987, 30, 1818. |
| 【2】 Andree, T.; Abou-Gharbia, M.; WY-47384. Drugs Fut 1988, 13, 6, 541. |
| 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) | 13486 | Ethyl 4-oxo-1-piperidinecarboxylate; N-Carbethoxy-4-piperidone | 29976-53-2 | C8H13NO3 | 详情 | 详情 |
| (I) | 22135 | 1-(4-fluorophenyl)hydrazine | 371-14-2 | C6H7FN2 | 详情 | 详情 |
| (III) | 22137 | ethyl 8-fluoro-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate | C14H15FN2O2 | 详情 | 详情 | |
| (IV) | 14941 | 8-fluoro-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole | 39876-39-6 | C11H11FN2 | 详情 | 详情 |
| (V) | 22139 | 3-(3-bromopropyl)pyridine | C8H10BrN | 详情 | 详情 |