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Article Navigation >  Journal of Pharmaceutical Practice and Service  > 2014  >  32(4): 290-293

XU Xiaoxia, MIN Tao, SHI Weilong. Improved synthesis of imatinib mesylate[J]. Journal of Pharmaceutical Practice and Service, 2014, 32(4): 290-293. doi: 10.3969/j.issn.1006-0111.2014.04.014
Citation: XU Xiaoxia, MIN Tao, SHI Weilong. Improved synthesis of imatinib mesylate[J]. Journal of Pharmaceutical Practice and Service, 2014, 32(4): 290-293. doi: 10.3969/j.issn.1006-0111.2014.04.014
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Improved synthesis of imatinib mesylate

doi: 10.3969/j.issn.1006-0111.2014.04.014

  • Nanjing Yoko Pharmaceutical Co. LTD, Nanjing 210008, China

  • Received Date: 2013-03-12
  • Rev Recd Date: 2013-12-05
  • Objective To obtain the improved synthesis of imatinib mesylate. Methods 4-[(4-methyl-piperazin-1-yl) methyl] benzoyl chloride dihydrochloride and 4-methyl-N3-[4-(3-pyridyl) pyrimidin-2-yl]-1,3-phenylenediamine were used as starting raw material to perform a condensation reaction in the aqueous phase to give imatinib free base, which was then neutralized with methanesulfonic acid to obtain the novel antineoplastic tyrosinase inhibitor imatinib mesylate by the use of a two-step reaction. Results The improved synthesis was considered to have the advantages of low cost, easy post-processing, high purity, high yield and environmental pollution with the HPLC purity≥99.7% and the single impurity<0.1%. Conclusion The total yield of the novel method was 81.5%, having an enough broad industrial production prospect.The targeted compound structure was confirmed by 1H NMR and ESI-MS.
  • [1] 陈 敖,黄荷香,宋帅娟. 甲磺酸伊马替尼的合成[J]. 精细与专用化学品,2007,15(8):23-25.
    [2] 赵 瑾,姜 达. 甲磺酸伊马替尼耐药机制及其逆转研究进展[J]. 癌症进展杂志,2009,7(2):158-165.
    [3] 陈灵娟,周和平,黄文峰,等. 甲磺酸伊马替尼的合成[J]. 河北科技大学学报,2011,32(5):492-495.
    [4] 王保国,刘玉凤,狄国杰. 甲磺酸伊马替尼的合成[J]. 济宁医学院学报,2012,35(2):103-105.
    [5] 齐默尔曼 J. 嘧啶衍生物及其制备方法[P]. 中国专利,93103566,1993-10-27.
    [6] Kompella A,Bhujanga RA,Venkaiah CN,et al. Process for the preparation of the anti-cancer drug imatinib and its analogues[P]. 世界专利,2004108699,2004-12-16.
    [7] 卢瓦瑟勒尔, 考夫曼, 阿贝尔,等. N-苯基-2-嘧啶胺衍生物[P]. 中国专利,03803556,2003-02-06.
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Improved synthesis of imatinib mesylate

doi: 10.3969/j.issn.1006-0111.2014.04.014
  • Nanjing Yoko Pharmaceutical Co. LTD, Nanjing 210008, China
  • Received Date: 2013-03-12
  • Rev Recd Date: 2013-12-05

Abstract: Objective To obtain the improved synthesis of imatinib mesylate. Methods 4-[(4-methyl-piperazin-1-yl) methyl] benzoyl chloride dihydrochloride and 4-methyl-N3-[4-(3-pyridyl) pyrimidin-2-yl]-1,3-phenylenediamine were used as starting raw material to perform a condensation reaction in the aqueous phase to give imatinib free base, which was then neutralized with methanesulfonic acid to obtain the novel antineoplastic tyrosinase inhibitor imatinib mesylate by the use of a two-step reaction. Results The improved synthesis was considered to have the advantages of low cost, easy post-processing, high purity, high yield and environmental pollution with the HPLC purity≥99.7% and the single impurity<0.1%. Conclusion The total yield of the novel method was 81.5%, having an enough broad industrial production prospect.The targeted compound structure was confirmed by 1H NMR and ESI-MS.

XU Xiaoxia, MIN Tao, SHI Weilong. Improved synthesis of imatinib mesylate[J]. Journal of Pharmaceutical Practice and Service, 2014, 32(4): 290-293. doi: 10.3969/j.issn.1006-0111.2014.04.014
Citation: XU Xiaoxia, MIN Tao, SHI Weilong. Improved synthesis of imatinib mesylate[J]. Journal of Pharmaceutical Practice and Service, 2014, 32(4): 290-293. doi: 10.3969/j.issn.1006-0111.2014.04.014
shu

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