Process Development and Synthesis of Process-Related Impurities of an Efficient Scale-Up Preparation of 5,2'-Dibromo-2,4',5'-Trihydroxy Diphenylmethanone as a New Acute Pyelonephritis Candidate Drug
Based on a foregoing gram-scale laboratory process, an efficient scale-up preparation process of 5,2'-dibromo-2,4',5'-trihydroxydiphenylmethanone ( ), a new acute pyelonephritis candidate drug, was developed and validated aiming to reduce by-products and achieve better impurity profil...
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Published in | Molecules (Basel, Switzerland) Vol. 25; no. 3; p. 468 |
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Main Authors | , , , , |
Format | Journal Article |
Language | English |
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Abstract | Based on a foregoing gram-scale laboratory process, an efficient scale-up preparation process of 5,2'-dibromo-2,4',5'-trihydroxydiphenylmethanone (
), a new acute pyelonephritis candidate drug, was developed and validated aiming to reduce by-products and achieve better impurity profiles. Meanwhile, the polymorph of
and process-related impurities were also investigated. Ultimately, the optimal reaction conditions were verified by evaluating the impurity profiles and their formation during the synthesis. Six process-related impurities were synthesized and identified, being useful for the quality control of
. Its finalized preparation process was further validated at 329-410 g scale-up production in 53.4-57.1% overall yield with 99.95-99.98% high-performance liquid chromatography (HPLC) purity, and it is currently viable for commercial production.
and
were identified as the main single impurities in
, with the content controlled to be less than 0.03%. |
---|---|
AbstractList | Based on a foregoing gram-scale laboratory process, an efficient scale-up preparation process of 5,2′-dibromo-2,4′,5′-trihydroxydiphenylmethanone (
LM49-API
), a new acute pyelonephritis candidate drug, was developed and validated aiming to reduce by-products and achieve better impurity profiles. Meanwhile, the polymorph of
LM49-API
and process-related impurities were also investigated. Ultimately, the optimal reaction conditions were verified by evaluating the impurity profiles and their formation during the synthesis. Six process-related impurities were synthesized and identified, being useful for the quality control of
LM49-API
. Its finalized preparation process was further validated at 329–410 g scale-up production in 53.4–57.1% overall yield with 99.95–99.98% high-performance liquid chromatography (HPLC) purity, and it is currently viable for commercial production.
LM49-API-imC
and
LM49-API-imX
were identified as the main single impurities in
LM49-API
, with the content controlled to be less than 0.03%. Based on a foregoing gram-scale laboratory process, an efficient scale-up preparation process of 5,2′-dibromo-2,4′,5′-trihydroxydiphenylmethanone (LM49-API), a new acute pyelonephritis candidate drug, was developed and validated aiming to reduce by-products and achieve better impurity profiles. Meanwhile, the polymorph of LM49-API and process-related impurities were also investigated. Ultimately, the optimal reaction conditions were verified by evaluating the impurity profiles and their formation during the synthesis. Six process-related impurities were synthesized and identified, being useful for the quality control of LM49-API. Its finalized preparation process was further validated at 329–410 g scale-up production in 53.4–57.1% overall yield with 99.95–99.98% high-performance liquid chromatography (HPLC) purity, and it is currently viable for commercial production. LM49-API-imC and LM49-API-imX were identified as the main single impurities in LM49-API, with the content controlled to be less than 0.03%. Based on a foregoing gram-scale laboratory process, an efficient scale-up preparation process of 5,2′-dibromo-2,4′,5′-trihydroxydiphenylmethanone (LM49-API), a new acute pyelonephritis candidate drug, was developed and validated aiming to reduce by-products and achieve better impurity profiles. Meanwhile, the polymorph of LM49-API and process-related impurities were also investigated. Ultimately, the optimal reaction conditions were verified by evaluating the impurity profiles and their formation during the synthesis. Six process-related impurities were synthesized and identified, being useful for the quality control of LM49-API. Its finalized preparation process was further validated at 329−410 g scale-up production in 53.4−57.1% overall yield with 99.95−99.98% high-performance liquid chromatography (HPLC) purity, and it is currently viable for commercial production. LM49-API-imC and LM49-API-imX were identified as the main single impurities in LM49-API, with the content controlled to be less than 0.03%. Based on a foregoing gram-scale laboratory process, an efficient scale-up preparation process of 5,2'-dibromo-2,4',5'-trihydroxydiphenylmethanone ( ), a new acute pyelonephritis candidate drug, was developed and validated aiming to reduce by-products and achieve better impurity profiles. Meanwhile, the polymorph of and process-related impurities were also investigated. Ultimately, the optimal reaction conditions were verified by evaluating the impurity profiles and their formation during the synthesis. Six process-related impurities were synthesized and identified, being useful for the quality control of . Its finalized preparation process was further validated at 329-410 g scale-up production in 53.4-57.1% overall yield with 99.95-99.98% high-performance liquid chromatography (HPLC) purity, and it is currently viable for commercial production. and were identified as the main single impurities in , with the content controlled to be less than 0.03%. |
Author | Lei, Fei Cui, Ke Meng Wu, Zi Cheng Li, Qing Shan Feng, Xiu E |
AuthorAffiliation | 1 School of Pharmaceutical Science, Shanxi Medical University, 56 Xinjian South Road, Taiyuan 030001, China; cuikem913@163.com 2 Shanxi Key laboratory of Chronic Inflammatory Targeted Drugs, School of Chinese Materia Medica, Shanxi University of Traditional Chinese Medicine, 121 University Street, Jinzhong 030602, China 3 Beijing Zhendong Guangming Pharmaceutical Research Institute, 18 Chuangye Road, Beijing 100089, China; wuzicheng@zdjt.com (Z.C.W.); leifei@zdjt.com (F.L.) |
AuthorAffiliation_xml | – name: 3 Beijing Zhendong Guangming Pharmaceutical Research Institute, 18 Chuangye Road, Beijing 100089, China; wuzicheng@zdjt.com (Z.C.W.); leifei@zdjt.com (F.L.) – name: 1 School of Pharmaceutical Science, Shanxi Medical University, 56 Xinjian South Road, Taiyuan 030001, China; cuikem913@163.com – name: 2 Shanxi Key laboratory of Chronic Inflammatory Targeted Drugs, School of Chinese Materia Medica, Shanxi University of Traditional Chinese Medicine, 121 University Street, Jinzhong 030602, China |
Author_xml | – sequence: 1 givenname: Xiu E surname: Feng fullname: Feng, Xiu E organization: School of Pharmaceutical Science, Shanxi Medical University, 56 Xinjian South Road, Taiyuan 030001, China – sequence: 2 givenname: Ke Meng surname: Cui fullname: Cui, Ke Meng organization: School of Pharmaceutical Science, Shanxi Medical University, 56 Xinjian South Road, Taiyuan 030001, China – sequence: 3 givenname: Qing Shan surname: Li fullname: Li, Qing Shan organization: Shanxi Key laboratory of Chronic Inflammatory Targeted Drugs, School of Chinese Materia Medica, Shanxi University of Traditional Chinese Medicine, 121 University Street, Jinzhong 030602, China – sequence: 4 givenname: Zi Cheng surname: Wu fullname: Wu, Zi Cheng organization: Beijing Zhendong Guangming Pharmaceutical Research Institute, 18 Chuangye Road, Beijing 100089, China – sequence: 5 givenname: Fei surname: Lei fullname: Lei, Fei organization: Beijing Zhendong Guangming Pharmaceutical Research Institute, 18 Chuangye Road, Beijing 100089, China |
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Cites_doi | 10.1016/j.intimp.2019.04.034 10.3390/molecules200814254 10.1155/2017/7028478 10.1039/C9RA05532K 10.1007/s11426-017-9192-x 10.1016/j.molstruc.2019.07.024 10.1093/cid/ciw378 10.1021/acs.iecr.9b02780 10.1111/jcmm.13948 10.1021/acs.oprd.9b00182 10.1016/j.polymdegradstab.2011.01.033 10.1007/s10096-019-03679-9 10.1016/j.bmcl.2010.05.068 10.1016/j.jpba.2010.05.002 10.1086/519268 10.1007/s40242-016-5233-4 10.1016/j.tetlet.2012.11.118 10.1016/j.intimp.2018.07.001 10.1093/cid/ciq257 10.1016/j.ejps.2017.05.013 10.1016/j.tetlet.2012.08.111 |
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Keywords | acute pyelonephritis 5,2′-dibromo-2,4′,5′-trihydroxydiphenylmethanone process-related impurity process development polymorph |
Language | English |
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Snippet | Based on a foregoing gram-scale laboratory process, an efficient scale-up preparation process of 5,2'-dibromo-2,4',5'-trihydroxydiphenylmethanone (
), a new... Based on a foregoing gram-scale laboratory process, an efficient scale-up preparation process of 5,2′-dibromo-2,4′,5′-trihydroxydiphenylmethanone (LM49-API), a... Based on a foregoing gram-scale laboratory process, an efficient scale-up preparation process of 5,2'-dibromo-2,4',5'-trihydroxydiphenylmethanone (LM49-API), a... Based on a foregoing gram-scale laboratory process, an efficient scale-up preparation process of 5,2′-dibromo-2,4′,5′-trihydroxydiphenylmethanone ( LM49-API ),... |
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SubjectTerms | 5,2′-dibromo-2,4′,5′-trihydroxydiphenylmethanone acute pyelonephritis Chloride Chromatography Drug dosages Drug resistance High performance liquid chromatography Impurities Laboratories Liquid chromatography polymorph process development process-related impurity Pyelonephritis Quality control R&D Reagents Research & development |
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Title | Process Development and Synthesis of Process-Related Impurities of an Efficient Scale-Up Preparation of 5,2'-Dibromo-2,4',5'-Trihydroxy Diphenylmethanone as a New Acute Pyelonephritis Candidate Drug |
URI | https://www.ncbi.nlm.nih.gov/pubmed/31979084 https://www.proquest.com/docview/2436585024 https://search.proquest.com/docview/2345507100 https://pubmed.ncbi.nlm.nih.gov/PMC7037700 https://doaj.org/article/f0bd7ad0bfef4afabaf93768db680c3a |
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