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【结 构 式】 
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【药物名称】 【化学名称】2-[4-(4-Chlorophenyl)-3-methyl-7-oxoisoxazolo[3,4-d]pyridazin-6-yl]acetic acid 【CA登记号】 【 分 子 式 】C14H10ClN3O4 【 分 子 量 】319.7065 |
【开发单位】Istituto Chimico Farm. e Tossicol. (Originator), Università degli Studi di Firenze (Originator), Università degli Studi di Modena (Originator) 【药理作用】ENDOCRINE DRUGS, Treatment of Diabetic Complications, Aldose Reductase Inhibitors |
合成路线1
Condensation of ketoester (I) with ethyl chloro(hydroxymino)acetate (II) provided isoxazole (III), which was cyclized to isoxazolopyridazine (IV) using hydrazine. Alkylation of (II) with ethyl bromoacetate gave ester (V), which was finally hydrolyzed with NaOH to afford the title carboxylic acid.
| 【1】 Ciciani, G.; et al.; 5-Acyl-6-aryl-4-nitro-3(2H)pyridazinones and related 4-amino compounds: Synthesis and pharmacological evaluation. J Pharm Sci 1991, 80, 4, 341-348. |
| 【2】 Barlocco, D.; Vianello, P.; Dal Piaz, V.; Constantino, L.; Giovannoni, M.P.; Gamberini, C.; Rastelli, G.; Isoxazolo-[3,4-d]-pyridazin-7-(6H)-one as a potential substrate for new aldose reductase inhibitors. J Med Chem 1999, 42, 11, 1894. |
| 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) | 30423 | ethyl 3-(4-chlorophenyl)-3-oxopropanoate | C11H11ClO3 | 详情 | 详情 | |
| (II) | 30424 | 2-ethoxy-N-hydroxy-2-oxoethanimidoyl chloride | 14337-43-0 | C4H6ClNO3 | 详情 | 详情 |
| (III) | 30425 | ethyl 4-(4-chlorobenzoyl)-5-methyl-3-isoxazolecarboxylate | C14H12ClNO4 | 详情 | 详情 | |
| (IV) | 30426 | 4-(4-chlorophenyl)-3-methylisoxazolo[3,4-d]pyridazin-7(6H)-one | C12H8ClN3O2 | 详情 | 详情 | |
| (V) | 30427 | ethyl 2-[4-(4-chlorophenyl)-3-methyl-7-oxoisoxazolo[3,4-d]pyridazin-6(7H)-yl]acetate | C16H14ClN3O4 | 详情 | 详情 |
Extended Information