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【结 构 式】 
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【药物名称】Nerisopam, EGIS-6775, GYKI-52322 【化学名称】1-(4-Aminophenyl)-4-methyl-7,8-dimethoxy-5H-2,3-benzodiazepine 【CA登记号】102771-12-0, 102771-15-3 (diHCl), 102771-14-2 (monoHCl), 102771-16-4 (sulfate) 【 分 子 式 】C18H19N3O2 【 分 子 量 】309.37103 |
【开发单位】Egis (Originator), Japan Tobacco (Licensee) 【药理作用】Antipsychotic Drugs, Anxiolytics, PSYCHOPHARMACOLOGIC DRUGS, Benzodiazepines |
合成路线1
1-(3,4-Dimethoxyphenyl)-2-propanol (I) is condensed with 4-nitrobenzaldehyde. The resulting 1-(4-nitrophenyl)-3-methyl-6,7-dimethoxyisochromane (II) is oxidized with Jones reagent to obtain 2-acetonyl-4,5-dimethoxy-4'-nitrobenzophenone (III). Then 1-(4-nitrophenyl)-3-methyl-6,7-dimethoxy-2-benzopyrylium perchlorate (IV) is produced by the conventional procedure, from which intermediary, with the help of hydrazine hydrate and reduction. GYKI-52322 is prepared.
| 【1】 Lang, T.; Korösi, J.; Andrási, F.; Botka, P.; Hámori, T.; Berzsenyi, P.; Goldschmidt, K.; Zólyomi, G.; Elekes, I.; Láng, Z. (Egis Pharmaceuticals Ltd.); 5H-2,3-Benzodiazepine derivs. and pharmaceutical c. BE 0902953; CH 667090; DE 3527117; ES 8608494; FR 2568252; GB 2162184; JP 1986043174; US 4614740 . |
| 【2】 Somogyi, G.; Balogh, T.; Botka, P.; Lang, T.; Hamori, T.; Lang, T.; Zolyomi, G.; Koeroesi, J. (Gyogyszerkutato Intezet Kft.); New process for producing 2-aroyl-phenylacetone derivs.. HU 194529 . |
| 【3】 Hamori, T.; Botka, P.; Zolyomi, G.; Koeroesi, J.; Lang, T.; Lang, T. (Gyogyszerkutato Intezet Kft.); Process for preparing isochromane derivs.. HU 194550 . |
| 【4】 Andrasi, F.; GYKI-52322. Drugs Fut 1988, 13, 4, 308. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 18184 | 4-Nitrobenzaldehyde | 555-16-8 | C7H5NO3 | 详情 | 详情 |
| (I) | 22077 | 1-(3,4-dimethoxyphenyl)-2-propanol | 161121-02-4 | C11H16O3 | 详情 | 详情 |
| (II) | 22078 | 6,7-dimethoxy-3-methyl-1-(4-nitrophenyl)-3,4-dihydro-1H-isochromene; 6-methoxy-3-methyl-1-(4-nitrophenyl)-3,4-dihydro-1H-isochromen-7-yl methyl ether | C18H19NO5 | 详情 | 详情 | |
| (III) | 22079 | 1-[4,5-dimethoxy-2-(4-nitrobenzoyl)phenyl]acetone | C18H17NO6 | 详情 | 详情 | |
| (IV) | 22080 | 6,7-dimethoxy-3-methyl-1-(4-nitrophenyl)isochromenium | C18H16NO5 | 详情 | 详情 |