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【结 构 式】 
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【药物名称】Y-700 【化学名称】1-[3-Cyano-4-(2,2-dimethylpropoxy)phenyl]-1H-pyrazole-4-carboxylic acid 【CA登记号】206884-98-2 【 分 子 式 】C16H17N3O3 【 分 子 量 】299.33219 |
【开发单位】Mitsubishi Pharma (Originator) 【药理作用】METABOLIC DRUGS, Treatment of Disorders of Purine and Pyrimidine Metabolism, Treatment of Gout, Xanthine Oxidase Inhibitors |
合成路线1
2-Cyano-3-neopentyloxyaniline (I) was diazotized with NaNO2/HCl and then reduced with SnCl2 to give hydrazine (II). The required pyrazole system (IV) was then obtained by condensation of hydrazine (II) with ethyl 2-cyano-3-ethoxyacrylate (III). Deamination of (IV) was achieved by diazotization of the amino group by means of isoamyl nitrite, with concomitant decomposition of the diazonium salt in refluxing THF to yield (V). Finally, saponification of the ethyl ester group of (V) provided the title carboxylic acid.
| 【1】 Ishibuchi, S.; et al.; Synthesis and structure-activity relationships of 1-phenylpyrazoles as xanthine oxidase inhibitors. Bioorg Med Chem Lett 2001, 11, 7, 879. |
| 【2】 Ishibuchi, S.; Morimoto, H.; Inoue, H.; Naka, Y.; Fukunari, A. (Welfide Corporation); 1-Phenylpyrazole cpds. and medicinal application thereof. EP 0936217; US 6015829; WO 9818765 . |
| 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) | 43752 | 5-amino-2-(neopentyloxy)benzonitrile | C12H16N2O | 详情 | 详情 | |
| (II) | 43753 | 5-hydrazino-2-(neopentyloxy)benzonitrile | C12H17N3O | 详情 | 详情 | |
| (III) | 43563 | ethyl (E)-2-cyano-3-ethoxy-2-propenoate；(E)-ethyl 2-cyano-3-ethoxyacrylate | 94-05-3 | C8H11NO3 | 详情 | 详情 |
| (IV) | 43754 | ethyl 5-amino-1-[3-cyano-4-(neopentyloxy)phenyl]-1H-pyrazole-4-carboxylate | C18H22N4O3 | 详情 | 详情 | |
| (V) | 43755 | ethyl 1-[3-cyano-4-(neopentyloxy)phenyl]-1H-pyrazole-4-carboxylate | C18H21N3O3 | 详情 | 详情 |