Synthesis of One Carbon-14 Labelled [14C-pyrazolo]-Ibrutinib

IF 0.9 4区 医学 Q4 BIOCHEMICAL RESEARCH METHODS
Pei Su, Bin Dong, Lei Xu, Zheng-Min Yang
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引用次数: 0

Abstract

A safe and economical synthetic method for one new carbon-14 labelled 1-[(3R)-3-[4-amino-3-(4-phenoxyphenyl)-[14C-pyrazolo]-1Hpyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinyl]-2-propen-1-one, [14C-pyrazolo]-Ibrutinib (2) was prepared with [14C]-barium carbonate as starting material, achieving a total yield of 19% with radiochemical and chemical purities exceeding 98%. The synthesis pathway was compared with existing methods, particularly those described in Janssen's patent applications, which offer higher yields but with more complex synthetic processes and lower purity. Despite the existing literature reporting the synthesis of 13C-labelled Ibrutinib, the 14C labelled method described here provides a viable alternative, particularly in some application fields necessitating the radioactive isotopic tracer technique. This work underscores the ongoing need for improved synthetic routes that offer higher yields, milder reaction conditions, and lower costs in light of the growing interest in Ibrutinib due to its clinical efficacy and commercial potential.

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碳-14标记[14c -吡唑啉]-伊鲁替尼的合成。
以[14C]-碳酸钡为原料,制备了一种安全、经济的新碳-14标记物1-[(3R)-3-[4-氨基-3-(4-苯氧苯基)-[14C-吡唑]-1- hpyrazolo [3,4-d]嘧啶-1-基]-1-哌啶基]-2-丙烯-1- 1,[14C-吡唑]-伊鲁替尼(2)的合成方法,总收率为19%,放射化学纯度超过98%。该合成途径与现有方法进行了比较,特别是与Janssen专利申请中描述的方法进行了比较,后者的产量更高,但合成过程更复杂,纯度更低。尽管已有文献报道了13c标记Ibrutinib的合成,但本文描述的14C标记方法提供了一种可行的替代方法,特别是在一些需要放射性同位素示踪技术的应用领域。鉴于伊鲁替尼的临床疗效和商业潜力,人们对其越来越感兴趣,这项工作强调了对更高收率、更温和的反应条件和更低成本的合成路线的持续需求。
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来源期刊
CiteScore
3.30
自引率
0.00%
发文量
57
审稿时长
1 months
期刊介绍: The Journal of Labelled Compounds and Radiopharmaceuticals publishes all aspects of research dealing with labeled compound preparation and applications of these compounds. This includes tracer methods used in medical, pharmacological, biological, biochemical and chemical research in vitro and in vivo. The Journal of Labelled Compounds and Radiopharmaceuticals devotes particular attention to biomedical research, diagnostic and therapeutic applications of radiopharmaceuticals, covering all stages of development from basic metabolic research and technological development to preclinical and clinical studies based on physically and chemically well characterized molecular structures, coordination compounds and nano-particles.
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