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【结 构 式】 
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【药物名称】Lanicemine hydrochloride, AR-R15896AR, FPL-15895AR((-)-enantiomer), FPL-15035AR(racemate), ARL-15896, FPL-15896AR(former code) 【化学名称】(+)-(S)-1-Phenyl-2-(2-pyridyl)ethylamine dihydrochloride 【CA登记号】153322-06-6, 153322-05-5 (free base) 【 分 子 式 】C13H16Cl2N2 【 分 子 量 】271.19187 |
【开发单位】AstraZeneca (Originator) 【药理作用】Cerebrovascular Diseases, Treatment of, Ischemic Stroke, Treatment of, NEUROLOGIC DRUGS, Stroke, Treatment of, NMDA Antagonists |
合成路线1
Addition of lithium bis(trimethylsilyl)amide to a cooled solution of benzaldehyde (I), followed by treatment with the lithiated anion of 2-picoline (II), gave rise to the silylated amino intermediate (III), which, upon acidic quenching, yielded the racemic alpha-phenyl-2-pyridineethanamine (IV). Resolution of amine (IV) with S-(+)-mandelic acid in EtOAc provided the target (S)-amine mandelate salt (V). Liberation of the free amine with NaOH and subsequent treatment with HCl in EtOAc furnished the corresponding dihydrochloride
| 【1】 Murray, R.J.; Mathisen, D.; Balestra, M. (Celltech Group plc); (S)-Alpha-phenyl-2-pyridineethanamine (S)-malate and its use as a medicament. EP 0691957; EP 0691958; JP 1996508292; JP 1996508475; WO 9422831; WO 9422832 . |
| 【2】 Griffith, R.C.; Murray, R.J.; Balestra, M. (Celltech Group plc); Enantiomeric 1-phenyl-2-(2-pyridinyl)ethylamine for the treatment of neurodegenerative disorders. EP 0633879; JP 2000319259; WO 9320052 . |
| 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) | 10498 | Benzaldehyde;Benzoic aldehyde;Phenylmethanal | 100-52-7 | C7H6O | 详情 | 详情 |
| (II) | 17590 | 2-methylpyridine; 2-picoline | 109-06-8 | C6H7N | 详情 | 详情 |
| (III) | 60500 | N-[1-phenyl-2-(2-pyridinyl)ethyl]-N,N-bis(trimethylsilyl)amine; trimethyl-N-[1-phenyl-2-(2-pyridinyl)ethyl]-N-(trimethylsilyl)silanamine | C19H30N2Si2 | 详情 | 详情 | |
| (IV) | 60501 | 1-phenyl-2-(2-pyridinyl)-1-ethanamine; 1-phenyl-2-(2-pyridinyl)ethylamine | C13H14N2 | 详情 | 详情 | |
| (V) | 60502 | C21H22N2O3 | 详情 | 详情 |