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【结 构 式】

【药物名称】Rimantadine hydrochloride, EXP-126, Oclovir, Flumadine, Roflual

【化学名称】alpha-Methyl-1-adamantanemethylamine hydrochloride
      alpha-Methyltricyclo[3.3.1.1(3,7)]decane-1-methanamine hydrochloride

【CA登记号】1501-84-4, 13392-28-4 (free base)

【 分 子 式 】C12H22ClN

【 分 子 量 】215.76884

【开发单位】Bristol-Myers Squibb (Originator), Roche (Originator), Forest (Licensee)

【药理作用】ANTIINFECTIVE THERAPY, Anti-Influenza A Virus Drugs, Anti-Influenza Virus Drugs, Antiviral Drugs

合成路线1

The compound can be obtained by two different ways: 1) The reaction of 1-acetyladamantane (I) with hydroxylamine gives the corresponding oxime (II), which is then reduced with LiAlH4 in THF. 2) By reaction of (I) with ammonia and H2 with a catalyst of Co on diatomite.

1 Brake, L.D. (DuPont Pharmaceuticals Co.); Verfahren zur Herstellung von alpha-Methyl-polycyclomethylaminen. CH 495944; DE 1668571; FR 1568056; US 3489802 .
2 Prichard, W.W. (DuPont Pharmaceuticals Co.); Adamantanes and tricyclo[4.3.1.1(3,8)]undecanes. FR 1572956; GB 1069563; NL 6408505; US 3352912 .
3 Serradell, M.N.; Castaner, J.; Robinson, C.P.; Rimantadine Hydrochloride. Drugs Fut 1984, 9, 9, 660.
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) 30600 1-(1-adamantyl)-1-ethanone; 1-Adamantyl methyl ketone; 1-acetyladamantane 1660-04-4 C12H18O 详情 详情
(II) 30601 1-(1-adamantyl)-1-ethanone oxime C12H19NO 详情 详情
Extended Information