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有机化学
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有机化学 ›› 2004, Vol. 24 ›› Issue (8): 890-892. 上一篇    下一篇

研究论文

盐酸吡格列酮的合成新方法研究

杨可锋a,b, 戴立言*,a, 陈英奇a   

  1. a浙江大学材料与化工学院制药工程研究所 杭州 310027
    b浙江华义医药有限公司 义乌 322002
  • 收稿日期:2003-10-08 修回日期:2003-12-22 接受日期:2004-02-16 发布日期:2022-09-20
  • 通讯作者: * E-mail: dailiyan@cmsce.zju.edu.cn; Tel: 0571-87952693.

New Synthetic Method of Pioglitazone Hydrochloride

YANG Ke-Fenga,b, DAI Li-Yan*,a, CHEN Ying-Qia   

  1. aInstitute of Pharmaceutical Engineering, College of Materials Scienceand Chemical Engineering, Zhejiang University, Hangzhou 310027
    bZhejiang Huayi Pharmaceutical Limited Company, Yiwu 322002
  • Received:2003-10-08 Revised:2003-12-22 Accepted:2004-02-16 Published:2022-09-20

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报道了治疗糖尿病药物盐酸吡格列酮的合成新方法.在六氢吡啶作用下,对羟基苯甲醛和2,4-噻唑烷二酮缩合生成5-[(4-羟苯基)亚甲基]-2,4-噻唑烷二酮,经钯炭催化氢化还原生成5-[(4-羟苯基)甲基]-2,4-噻唑烷二酮,再和氢氧化钾反应生成相应的钾盐,然后与5-乙基-2-羟乙基吡啶和甲基磺酰氯反应得到的磺酸酯作用生成吡格列酮,最后用盐酸酸化得到其盐酸盐.产品结构经1H NMR和IR确证.

关键词: 盐酸吡格列酮, 合成, 新方法

A new synthetic method of pioglitazone hydrochloride, a kind of drug for treating diabetes, was reported. With the piperidine as catalyst, p-hydroxybenzaldehyde condensed with 2,4-thiazolidinedione to give 5-(4-hydroxybenzylidene)thiazolidine-2,4-dione, which was reduced byhydrogen/Pd-C to afford 5-(4-hydroxybenzyl)~thiazolidine-2,4-dione. The dione subsequently reacted with potassium hydroxide and 2-(5-ethyl-2-pyridyl)ethyl sulfonate to produce pioglitazone, and finally with hydrochloride acid to obtain the hydrochloride salt. Some compounds were confirmed by 1HNMR and IR.

Key words: pioglitazone hydrochloride, synthesis, new method