【结 构 式】 |
【药物名称】Oxodipine, IQB-837V 【化学名称】Ethyl methyl 1,4-dihydro-2,6-dimethyl-4-[2,3-(methylenedioxy)phenyl]-3,5-pyridinedicarboxylate 【CA登记号】90729-41-2 【 分 子 式 】C19H21NO6 【 分 子 量 】359.38232 |
【开发单位】IIDQB (Originator) 【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
The cyclization of 2,3-dihydroxybenzaldehyde (I) with dibromomethane by means of KF in hot DMF gives 2,3-methylenedioxybenzaldehyde (II), which is condensed with ethyl acetoacetate (III) by means of piperidine and acetic acid in refluxing benzene to afford ethyl 2-acetyl-3-(2,3-methylenedioxyphenyl)acrylate (IV). Finally, this compound is cyclized with methyl 3-aminocrotonate (V) in hot isopropanol.
【1】 Galiano Ramos, J.A.; Verde Casanova, M.J. (IIDQB (Madrid); Laboratoires Delagrange); Calcium antagonists. BE 0902016; CH 663020; DE 3510762; EP 0158211; FR 2562069; GB 2156809; JP 1985248671; US 4722931 . |
【2】 Serradell, M.N.; Castaner, J.; Castaner, R.M.; Oxodipine. Drugs Fut 1987, 12, 7, 633. |
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) | 12380 | 2,3-Dihydroxybenzaldehyde | 24677-78-9 | C7H6O3 | 详情 | 详情 |
(II) | 13329 | 2,3-(Methylenedioxy)benzaldehyde; 1,3-Benzodioxole-4-carbaldehyde | 7797-83-3 | C8H6O3 | 详情 | 详情 |
(III) | 11819 | ethyl acetoacetate; ethyl 3-oxobutanoate;Acetoacetic ester;Ethyl beta-ketobutyrate;ethyl 3-oxobutyrate | 141-97-9 | C6H10O3 | 详情 | 详情 |
(IV) | 28848 | ethyl 2-(1,3-benzodioxol-4-ylmethyl)-3-oxobutanoate | C14H16O5 | 详情 | 详情 | |
(V) | 11372 | Methyl (E)-3-amino-2-butenoate; Methyl 3-aminocrotonate | C5H9NO2 | 详情 | 详情 |