Synthesis and Impurity Research of 2-Thioadenosine Monohydrate
Abstract 2-Thioadenosine monohydrate (1) is a vital intermediate in the synthesis of cangrelor. However, its industrial-scale preparation process and the analysis of the impurities formed during this process remained largely unknown. Herein, cangrelor was synthesized from oxidate adenosine...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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Georg Thieme Verlag KG
2023-06-01
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| Series: | Pharmaceutical Fronts |
| Subjects: | |
| Online Access: | http://www.thieme-connect.de/DOI/DOI?10.1055/s-0043-1768692 |
| _version_ | 1827936970756587520 |
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| author | Jing-Jing Xiang Bi-Bo Jiang Wen-Qing Sun Fu-Li Zhang Jun Yu |
| author_facet | Jing-Jing Xiang Bi-Bo Jiang Wen-Qing Sun Fu-Li Zhang Jun Yu |
| author_sort | Jing-Jing Xiang |
| collection | DOAJ |
| description | Abstract
2-Thioadenosine monohydrate (1) is a vital intermediate in the synthesis of cangrelor. However, its industrial-scale preparation process and the analysis of the impurities formed during this process remained largely unknown. Herein, cangrelor was synthesized from oxidate adenosine, and the key step involved in the synthesis of compound 1 from intermediate 5. The effects of key synthesis parameters that influenced the reaction, including reaction temperature and time, were discussed. Moreover, four process-related impurities were purified, synthesized, and identified via nuclear magnetic resonance spectroscopy and high-resolution mass spectrometry. The process can be utilized to produce 1 on a kilogram scale, with a high-performance liquid chromatography purity of 98.0%. The study sheds light on and helps drug manufacturers further understand the formation process of impurities in the preparation of cangrelor. |
| first_indexed | 2024-03-13T08:18:47Z |
| format | Article |
| id | doaj.art-84ac302ac52342e18adca1845399ef69 |
| institution | Directory Open Access Journal |
| issn | 2628-5088 2628-5096 |
| language | English |
| last_indexed | 2024-03-13T08:18:47Z |
| publishDate | 2023-06-01 |
| publisher | Georg Thieme Verlag KG |
| record_format | Article |
| series | Pharmaceutical Fronts |
| spelling | doaj.art-84ac302ac52342e18adca1845399ef692023-05-31T12:35:46ZengGeorg Thieme Verlag KGPharmaceutical Fronts2628-50882628-50962023-06-010502e84e9010.1055/s-0043-1768692Synthesis and Impurity Research of 2-Thioadenosine MonohydrateJing-Jing Xiang0Bi-Bo Jiang1Wen-Qing Sun2Fu-Li Zhang3Jun Yu4School of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, Shanghai, People's Republic of ChinaEngineering Research Center for Improvement and Industrialization of Pharmaceutical Processes, Shanghai Institute of Pharmaceutical Industry Co., Ltd., China State Institute of Pharmaceutical Industry, Shanghai, People's Republic of ChinaShandong Ruizhi Pharmaceutical Technology Co., Ltd., Heze, People's Republic of ChinaSchool of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, Shanghai, People's Republic of ChinaEngineering Research Center for Improvement and Industrialization of Pharmaceutical Processes, Shanghai Institute of Pharmaceutical Industry Co., Ltd., China State Institute of Pharmaceutical Industry, Shanghai, People's Republic of ChinaAbstract 2-Thioadenosine monohydrate (1) is a vital intermediate in the synthesis of cangrelor. However, its industrial-scale preparation process and the analysis of the impurities formed during this process remained largely unknown. Herein, cangrelor was synthesized from oxidate adenosine, and the key step involved in the synthesis of compound 1 from intermediate 5. The effects of key synthesis parameters that influenced the reaction, including reaction temperature and time, were discussed. Moreover, four process-related impurities were purified, synthesized, and identified via nuclear magnetic resonance spectroscopy and high-resolution mass spectrometry. The process can be utilized to produce 1 on a kilogram scale, with a high-performance liquid chromatography purity of 98.0%. The study sheds light on and helps drug manufacturers further understand the formation process of impurities in the preparation of cangrelor.http://www.thieme-connect.de/DOI/DOI?10.1055/s-0043-1768692cangrelor2-thioadenosine monohydratea kilogram scaleimpurities |
| spellingShingle | Jing-Jing Xiang Bi-Bo Jiang Wen-Qing Sun Fu-Li Zhang Jun Yu Synthesis and Impurity Research of 2-Thioadenosine Monohydrate Pharmaceutical Fronts cangrelor 2-thioadenosine monohydrate a kilogram scale impurities |
| title | Synthesis and Impurity Research of 2-Thioadenosine Monohydrate |
| title_full | Synthesis and Impurity Research of 2-Thioadenosine Monohydrate |
| title_fullStr | Synthesis and Impurity Research of 2-Thioadenosine Monohydrate |
| title_full_unstemmed | Synthesis and Impurity Research of 2-Thioadenosine Monohydrate |
| title_short | Synthesis and Impurity Research of 2-Thioadenosine Monohydrate |
| title_sort | synthesis and impurity research of 2 thioadenosine monohydrate |
| topic | cangrelor 2-thioadenosine monohydrate a kilogram scale impurities |
| url | http://www.thieme-connect.de/DOI/DOI?10.1055/s-0043-1768692 |
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