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【结 构 式】 
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【药物名称】Velnacrine maleate, P83-6029A, HP-029, Mentane 【化学名称】(±)-9-Amino-1,2,3,4-tetrahydroacridin-1-ol maleate 【CA登记号】118909-22-1, 112964-99-5 (former CAS), 121445-18-9 (former CAS), 104675-29-8 (free base), 112964-98-4 (free base, former CAS), 1 【 分 子 式 】C17H18N2O5 【 分 子 量 】330.34341 |
【开发单位】Aventis Pharma (Originator) 【药理作用】Cognition Disorders, Treatment of, NEUROLOGIC DRUGS, Acetylcholinesterase Inhibitors, Butyrylcholinesterase Inhibitors |
合成路线1
The condensation of anthranilonitrile (I) with cyclohexane-1,3-dione (II) in the presence of p-toluenesulfonic acid (removal of water) gives the enaminoketone (III). Cyclization of (III) in the presence of K2CO3 and CuCl yields the aminoketone (IV), which is then reduced with LiAlH4.
| 【1】 Shutske, G.M.; Pierrat, F.A. (Aventis Pharmaceuticals, Inc.); 9-Amino-1,2,3,4-tetrahydroacridin-1-ol and related cpds., a process for their preparation and their use as medicaments. AU 8549038; EP 0179383; ES 8701165; ES 8801213; ES 8802383; JP 1986148154; JP 1989125362; US 4631286; US 4839364 . |
| 【2】 Shutske, G.M.; VELNACRINE MALEATE < USAN >. Drugs Fut 1989, 14, 7, 643. |
合成路线2
The condensation of N-(2-methylquinolin-4-yl)acetamide (I) with 2-(2-iodoethyl)-1,3-dioxane (II) by means of LDA in THF gives the corresponding adduct (III), which is then cyclized and deacylated by means of aqueous HCl to afford the target tetrahydroacridine.
| 【1】 Caldero Ges, J.M.; Huguet Clotet, J. (Vita-Invest, SA); Process for the preparation of (±)-9-amino-1,2,3,4-tetrahydroacridin-1-ol. ES 2059263 . |