Practical and Sustainable Synthesis of Optically Pure Levocabastine, a H1 Receptor Antagonist
A practical and sustainable method for the synthesis of levocabastine hydrochloride (1), a H1 receptor antagonist for the treatment of allergic conjunctivitis, that can be applied to the industrial production of the compound has been developed. Substantial improvements over the previously reported p...
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| Format: | Article |
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MDPI AG
2017-11-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/22/11/1971 |
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| author | Sung Kwon Kang Dong Hyuk Nam Jaeseung Ahn Jaemin Lee Jaehoon Sim Jeeyeon Lee Young-Ger Suh |
| author_facet | Sung Kwon Kang Dong Hyuk Nam Jaeseung Ahn Jaemin Lee Jaehoon Sim Jeeyeon Lee Young-Ger Suh |
| author_sort | Sung Kwon Kang |
| collection | DOAJ |
| description | A practical and sustainable method for the synthesis of levocabastine hydrochloride (1), a H1 receptor antagonist for the treatment of allergic conjunctivitis, that can be applied to the industrial production of the compound has been developed. Substantial improvements over the previously reported procedure are achieved via efficient preparation of an optically active key intermediate (5) without chiral resolution and with a more effective detosylation, which complements the previous procedure. Notably, our process requires no chromatographic purification and provides levocabastine hydrochloride in greater than 99.5% purity in a 14.2% overall yield. |
| first_indexed | 2024-04-12T07:50:24Z |
| format | Article |
| id | doaj.art-cac33f4698da42f5a8d070136ce194d8 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-04-12T07:50:24Z |
| publishDate | 2017-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-cac33f4698da42f5a8d070136ce194d82022-12-22T03:41:36ZengMDPI AGMolecules1420-30492017-11-012211197110.3390/molecules22111971molecules22111971Practical and Sustainable Synthesis of Optically Pure Levocabastine, a H1 Receptor AntagonistSung Kwon Kang0Dong Hyuk Nam1Jaeseung Ahn2Jaemin Lee3Jaehoon Sim4Jeeyeon Lee5Young-Ger Suh6College of Pharmacy, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 08826, KoreaDepartment of Synthetic Chemistry, Chong Kun Dang Research Institute, 315-20, Dongbaekjukjeon-daero, Giheung-gu, Yongin-si 16995, Gyeonggi-do, KoreaDepartment of Synthetic Chemistry, Chong Kun Dang Research Institute, 315-20, Dongbaekjukjeon-daero, Giheung-gu, Yongin-si 16995, Gyeonggi-do, KoreaDepartment of Synthetic Chemistry, Chong Kun Dang Research Institute, 315-20, Dongbaekjukjeon-daero, Giheung-gu, Yongin-si 16995, Gyeonggi-do, KoreaCollege of Pharmacy, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 08826, KoreaCollege of Pharmacy, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 08826, KoreaCollege of Pharmacy, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 08826, KoreaA practical and sustainable method for the synthesis of levocabastine hydrochloride (1), a H1 receptor antagonist for the treatment of allergic conjunctivitis, that can be applied to the industrial production of the compound has been developed. Substantial improvements over the previously reported procedure are achieved via efficient preparation of an optically active key intermediate (5) without chiral resolution and with a more effective detosylation, which complements the previous procedure. Notably, our process requires no chromatographic purification and provides levocabastine hydrochloride in greater than 99.5% purity in a 14.2% overall yield.https://www.mdpi.com/1420-3049/22/11/1971levocabastineanti-histamineH1 receptor antagonist |
| spellingShingle | Sung Kwon Kang Dong Hyuk Nam Jaeseung Ahn Jaemin Lee Jaehoon Sim Jeeyeon Lee Young-Ger Suh Practical and Sustainable Synthesis of Optically Pure Levocabastine, a H1 Receptor Antagonist Molecules levocabastine anti-histamine H1 receptor antagonist |
| title | Practical and Sustainable Synthesis of Optically Pure Levocabastine, a H1 Receptor Antagonist |
| title_full | Practical and Sustainable Synthesis of Optically Pure Levocabastine, a H1 Receptor Antagonist |
| title_fullStr | Practical and Sustainable Synthesis of Optically Pure Levocabastine, a H1 Receptor Antagonist |
| title_full_unstemmed | Practical and Sustainable Synthesis of Optically Pure Levocabastine, a H1 Receptor Antagonist |
| title_short | Practical and Sustainable Synthesis of Optically Pure Levocabastine, a H1 Receptor Antagonist |
| title_sort | practical and sustainable synthesis of optically pure levocabastine a h1 receptor antagonist |
| topic | levocabastine anti-histamine H1 receptor antagonist |
| url | https://www.mdpi.com/1420-3049/22/11/1971 |
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