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【结 构 式】 
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【药物名称】Lacidipine, SN-305, GX-1048, GR-43659X, Viapres, Caldine, Motens, Lacipil, Lacirex 【化学名称】(E)-4-[2-[2-(tert-Butoxycarbonyl)vinyl]phenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester 【CA登记号】103890-78-4 【 分 子 式 】C26H33NO6 【 分 子 量 】455.55601 |
【开发单位】GlaxoSmithKline (Originator), Boehringer Ingelheim (Licensee), Zambon (Licensee) 【药理作用】CARDIOVASCULAR DRUGS, Hypertension, Treatment of, Calcium Channel Blockers |
合成路线1
The Wittig condensation of o-phthalaldehyde (I) with tert-butyl triphenylphosphoranylideneacetate (II) in methylene chloride gives tert-butyl 3-(2-formylphenyl)-2(E)-propenoate (III), which is then cyclized with ethyl 3-aminocrotonate (IV) in acetic acid.
| 【1】 Borthwick, A.D.; Pierccioli, D.; Micheli, D.; Semeraro, C.; Gaviraghi, G. (Glaxo SpA); 1,4-dihydropyridines.. ES 8703839; ES 8703839; US 4801599; US 5011848 . |
| 【2】 Prous, J.; Castaner, J.; LACIDIPINE < Rec INN; BAN; USAN >. Drugs Fut 1989, 14, 4, 317. |
| 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) | 19472 | o-phthalaldehyde; o-phthaldialdehyde; phthalaldehyde | 643-79-8 | C8H6O2 | 详情 | 详情 |
| (II) | 11335 | tert-butyl 2-(triphenyl-lambda(5)-phosphanylidene)acetate; (tert-Butoxycarbonylmethylene)triphenylphosphorane | 35000-38-5 | C24H25O2P | 详情 | 详情 |
| (III) | 19474 | tert-butyl (E)-3-(2-formylphenyl)-2-propenoate | C14H16O3 | 详情 | 详情 | |
| (IV) | 11975 | Ethyl (E)-3-amino-2-butenoate | 7318-00-5 | C6H11NO2 | 详情 | 详情 |
Extended Information