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【结 构 式】 
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【药物名称】Nicardipine hydrochloride, TN-901, RS-69216-XX-07-O, RS-69216, YC-93, Perpidine, Nerdipine, Loxen, Antagonil, Cardene, Perdipine, Nicodel 【化学名称】2,6-Dimethyl-4-(3-nitrophenyl)-3-methoxycarbonyl-1,4-dihydropyridine-5-carboxylic acid 2-(N-benzyl-N-methylamino)ethyl ester hydrochloride 【CA登记号】54527-84-3, 55985-32-5 (free base) 【 分 子 式 】C26H30ClN3O6 【 分 子 量 】515.9985 |
【开发单位】Yamanouchi (Originator), Nihon Schering (Not Determined), Ferrer (Licensee), Mitsui Chemicals (Licensee), Novartis (Licensee), Roche (Licensee) 【药理作用】Angina pectoris, Treatment of, CARDIOVASCULAR DRUGS, Hypertension, Treatment of, Treatment of Disorders of the Coronary Arteries and Atherosclerosis, Calcium Channel Blockers |
合成路线1
Compound can be prepared in two different ways: 1) By heating at 100 C a mixture of m-nitrobenzaldehyde (I), methyl beta-aminocrotonate (II) and N-benzyl-N-methylaminoethyl acetoacetate (III). 2) By cyclization of a mixture of m-nitrobenzaldehyde (I), methyl acetoacetate (IV) and N-benzyl-N-methylaminoethyl beta + aminocrotonate (V) in refluxing isopropanol.
| 【1】 Murakami, M.; et al.; BE 0811324 . |
| 【2】 Roberts, P.J.; Castaner, J.; YC-93. Drugs Fut 1977, 2, 6, 409. |
| 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) | 12646 | 3-Nitrobenzaldehyde | 99-61-6 | C7H5NO3 | 详情 | 详情 |
| (II) | 11372 | Methyl (E)-3-amino-2-butenoate; Methyl 3-aminocrotonate | C5H9NO2 | 详情 | 详情 | |
| (III) | 33898 | 2-[benzyl(methyl)amino]ethyl 3-oxobutanoate | C14H19NO3 | 详情 | 详情 | |
| (IV) | 11791 | methyl 3-oxobutanoate; Methyl acetoacetate | 105-45-3 | C5H8O3 | 详情 | 详情 |
| (V) | 33899 | 2-[benzyl(methyl)amino]ethyl (E)-3-amino-2-butenoate | C14H20N2O2 | 详情 | 详情 |