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【结 构 式】 
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【药物名称】Carvotroline hydrochloride, Wy-47791 【化学名称】8-Fluoro-2-[2-(4-pyridyl)ethyl]-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole hydrochloride 【CA登记号】107266-08-0 (free base), 136777-43-0 (monoHCl) 【 分 子 式 】C18H19ClFN3 【 分 子 量 】331.82363 |
【开发单位】Wyeth Pharmaceuticals (Originator) 【药理作用】Antipsychotic Drugs, PSYCHOPHARMACOLOGIC DRUGS, 5-HT2A Antagonists, Dopamine D2 Antagonists |
合成路线1
The reaction of 4-fluorophenylhydrazine, hydrochloride (I) with 4-piperidone hydrochloride hydrate (II) in refluxing ethanol afforded 8-fluoro-2,3,4,5-tetrahydro-1H-pyrido[4,3-b] indole (III) in 82% yield. Compound (III) was reacted with 4-vinylpyridine in THF in the presence of acetic acid to give WY-47,791 free base in 85% yield which was converted to the hydrochloride salt.
| 【1】 Moyer, J.A.; Andree, T.H.; Abou-Gharbia, M.; Patel, U.A.; Muth, E.A.; Webb, M.B.; Antipsychotic activity of substituted gamma-carbolines. J Med Chem 1987, 30, 1818-23. |
| 【2】 Abou-Gharbia, M.; Marquis, K.; Andree, T.; WY-47,791. Drugs Fut 1991, 16, 11, 1008. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 45857 | 4-vinylpyridine | C7H7N | 详情 | 详情 | ||
| (I) | 14939 | 4-Fluorophenylhydrazine hydrochloride; 1-(4-fluorophenyl)hydrazine hydrochloride | 823-85-8 | C6H8ClFN2 | 详情 | 详情 |
| (II) | 14940 | tetrahydro-4,4(1H)-pyridinediol hydrocloride | C5H12ClNO2 | 详情 | 详情 | |
| (III) | 14941 | 8-fluoro-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole | 39876-39-6 | C11H11FN2 | 详情 | 详情 |