• 中国精品科技期刊
  • 中国高校百佳科技期刊
  • 中国中文核心期刊
  • 中国科学引文数据库核心期刊
Advanced Search
WU Xufeng, CHAI Shiying, LIU Jianhong, WANG Zhihui, YIN Ruifeng, CAO Ruiwei, SUN Xinqiang. Improvement of synthetic route of brivudine[J]. Journal of China Pharmaceutical University, 2022, 53(1): 41-45. DOI: 10.11665/j.issn.1000-5048.20220106
Citation: WU Xufeng, CHAI Shiying, LIU Jianhong, WANG Zhihui, YIN Ruifeng, CAO Ruiwei, SUN Xinqiang. Improvement of synthetic route of brivudine[J]. Journal of China Pharmaceutical University, 2022, 53(1): 41-45. DOI: 10.11665/j.issn.1000-5048.20220106
shu

Improvement of synthetic route of brivudine

  • 1.

    Zhejiang Medicine Co., Ltd., Xinchang Pharmaceutical Factory, Shaoxing 312500

  • 2.

    Zhejiang Changhai Pharmaceutical Co., Ltd., Shaoxing 312366, China

More Information
  • Received Date: February 09, 2021
  • Revised Date: January 02, 2022
    Graphical Abstract
    • Abstract
  • This article summarizes and analyzes the reported synthetic routes of brivudine in patent and literature.2′-Deoxyuridine was employed as starting material, affording brivudine through iodization, heck coupling, hydrolysis, decarboxylation, bromination and recrystallization.After optimization of reaction conditions of each step, a synthetic route suitable for industrial production was achieved with simple synthetic process, high yield and excellent purity.
    • FullText(HTML)
    • References (20)
  • [1]
    . Chin J Clin （中国临床医生杂志），2003，31（5）：4-5.
    [2]
    Zhang B，Shen Q，Shi Q. Clinical observation of treating post-acute zoster pain by ganglioside M1［J］. Med J Wuhan Univ （武汉大学学报 医学版），2017，38（5）：790-793.
    [3]
    Katz J，Cooper EM，Walther RR，et al. Acute pain in Herpes zoster and its impact on health-related quality of life［J］. Clin Infect Dis，2004，39（3）：342-348.
    [4]
    Lin JY，Chen QM，Zhou HM. Research progress of antiherpes virus drugs［J］. Chin J Stomatol（中华口腔医学杂志），2006，41 （1）：60-62.
    [5]
    Liu WG，Guo RL，Chen ZJ. New selective anti-herpes virus drug：（E）-5-（2-bromovinyl）2′-deoxyuridine［J］. Chin J Exp Ophthalmol （中华实验眼科杂志），1985，3（2）：123-126.
    [6]
    Clereq ED. （E）-5-（2-Bromovinyl）-2′-deoxyuridine （BVDU）［J］. Med Res Rev，2005，25 （1）：1-20.
    [7]
    Wassilew S，Collaborative Brivudin PHN Study Group. Brivudin compared with famciclovir in the treatment of Herpes zoster：effects in acute disease and chronic pain in immunocompetent patients. A randomized，double-blind，multinational study［J］. J Eur Acad Dermatol Venereol，2005，19（1）：47-55.
    [8]
    Mao F，Wu ZX，Zhang L，et al. Therapeutic effect of bromovudine on 37 cases of herpes zoster［J］. Mod Pract Med （现代实用医学），2018，30 （4）：535-536.
    [9]
    Barr PJ，Clereq ED，Jones AS，et al. E-
    5-（2-halogenvinyl）-2′-desoxyuridine und deren verwendung als arzneimittel：
    DE2915254C2［P］. 1990-07-12.
    [10]
    Barr PJ，Jones AS，Verhelst G，et al. Synthesis of some 5-halogenovinyl derivatives of uracil and their conversion into 2′-deoxyribonucleosides［J］. J Chem Soc，Perkin Trans 1，1981：1665-1670.
    [11]
    Szabolcs A，Otvos L，Sagi J，et al. Process for the preparation of （E）-
    5-（2-bromovinyl）-2′-deoxyuridine and new derivatives thereof：
    GB2125399B［P］. 1987-04-01.
    [12]
    Aldo S，Alberto MC，Stefano M，et al. Process for the preparation of （E）-
    5-（2-bromovinyl）-2′-deoxyuridine：
    WO2002068443A1［P］. 2002-09-06.
    [13]
    Zhang WB，Xie F，Wang CJ. Method for the preparation of bromovudine：
    CN101066987B［P］. 2010-05-19.
    [14]
    Ashwell M，Jones AS，Kumar A，et al. The synthesis and antiviral properties of （E）-5-（2-bromovinyl）-2′-deoxyuridine-related compounds［J］. Tetrahedron，1987，43（20）：4601-4608.
    [15]
    Asakura J，Robins MJ. Cerium（IV）-mediated halogenation at C-5 of uracil derivatives［J］. J Org Chem，1990，55（16）：4928-4933.
    [16]
    Jones AS，Verhelst G，Walker RT. The synthesis of the potent anti-Herpes virus agent，E-5（2-bromovinyl）-2′-deoxyuridine and related compounds［J］. Tetrahedron Lett，1979，20（45）：4415-4418.
    [17]
    Kassis AI，Foulon CF，James Adelstein S. Rapid synthesis of radiolabeled pyrimidine nucleosides or nucleotides：
    US5574148［P］. 1996-11-12.
    [18]
    Chinese Pharmacopoeia Commission. Chinese Pharmacopoeia：part 2［S］. Beijing：China Medical Science Press，2020：1741.
    [19]
    Kumar R，Wiebe LI，Knaus EE. A mild and efficient methodology for the synthesis of 5-halogeno uracil nucleosides that occurs via a 5-halogeno-6-azido-5，6-dihydro intermediate［J］. Can J Chem，1994，72（9）：2005-2010.
    [20]
    Eger K，Jalalian M，Schmidt M. Steric fixation of bromovinyluracil：synthesis of furo［2，3-d］pyrimidine nucleosides［J］. J Heterocycl Chem，1995，32（1）：211-218.
    • Related Articles

  • Related Articles

    [1]LIU Li, LIU Zijin, TANG Jun, HE Guangwei, LIU Weizhong. Optimized synthesis process of tofacitinib citrate[J]. Journal of China Pharmaceutical University, 2022, 53(6): 685-689. DOI: 10.11665/j.issn.1000-5048.20220606
    [2]WANG Dong, ZHONG Jian, WANG Ling, ZHOU Zhihui, JIANG Haiting, LUO Peng, WANG Xizhi, WANG Chongyi. Improved synthetic process of apremilast[J]. Journal of China Pharmaceutical University, 2021, 52(5): 536-540. DOI: 10.11665/j.issn.1000-5048.20210504
    [3]HAN Chengqun, ZOU Qiaogen, SUN Qian, XIA Yunyan. Improvement of synthesis process of mirabegron[J]. Journal of China Pharmaceutical University, 2020, 51(4): 449-453. DOI: 10.11665/j.issn.1000-5048.20200409
    [4]ZHANG Qiuyue, YOU Qidong, YANG Jinpeng. Process improvement on the synthesis of atomoxetine[J]. Journal of China Pharmaceutical University, 2019, 50(4): 405-409. DOI: 10.11665/j.issn.1000-5048.20190404
    [5]LIU Li, WANG Chen, LIU Lixin, JI Tingting. Improved synthesis of analgesic pentazocine[J]. Journal of China Pharmaceutical University, 2018, 49(5): 568-571. DOI: 10.11665/j.issn.1000-5048.20180508
    [6]ZHANG Chunlai, LUO Hongjun, JIANG Qi, LI Guoxian, GU Guoqing, ZHANG Jie. Improved process of dexrabeprazole sodium[J]. Journal of China Pharmaceutical University, 2018, 49(3): 291-294. DOI: 10.11665/j.issn.1000-5048.20180306
    [7]MA Li, ZHANG Menghan, XU Zhiwei, SUN Ying′ai, ZHU Jing, HUANG Yingbo, ZHANG Dayong. A new synthetic process of dapagliflozin[J]. Journal of China Pharmaceutical University, 2017, 48(1): 42-45. DOI: 10.11665/j.issn.1000-5048.20170106
    [8]WEI Qingjie, QIAO Junhua, CHEN Jianjun, GAO Zhigang, LI Yaqing. An improvement for synthesis of ceftriaxone sodium[J]. Journal of China Pharmaceutical University, 2016, 47(2): 163-165. DOI: 10.11665/j.issn.1000-5048.20160206
    [9]WU Jiaquan, ZHOU Ping, LIU Yang, JIE Chuanming, CAO Huanyan, PENG Tao, LI Xiaohong, ZHANG Haijun. An improved preparing process for rivastigmine[J]. Journal of China Pharmaceutical University, 2015, 46(4): 421-425. DOI: 10.11665/j.issn.1000-5048.20150406
    [10]Improve on the Synthetic Process of Bezafibrate[J]. Journal of China Pharmaceutical University, 2003, (3): 80-81.

Catalog

    Get Citation
    PDF
    XML
    Article views (248) PDF downloads (413) Cited by()
    Turn off MathJax
    Article Contents
    Abstract
    References
    Related Articles

    Copyright © Journal of China Pharmaceutical University苏ICP备12050101号-2

    Address：24 Tongjia Lane, Nanjing City, Jiangsu Province （210009）Tel: 025-83271566E-mail: xuebao@cpu.edu.cn

    Supported by: Beijing Renhe Information Technology Co., Ltd.  Baidu Analytics

    Total visits：282528

    /

    DownLoad:  Full-Size Img  PowerPoint
    Return
    Return