Chemistry:Revefenacin
Revefenacin, sold under the brand name Yupelri, is a medication for the treatment of chronic obstructive pulmonary disease (COPD). It was approved for use in the United States in 2018.[1] It was developed by Theravance Biopharma and is marketed by Mylan. Revefenacin is formulated as a solution that is nebulized and inhaled.[2]
Revefenacin is a bronchodilator that exerts its effect as a long-acting muscarinic antagonist.[3]
Society and culture
Brand names
In some countries, Yupelri is marketed by Viatris after Upjohn merged with Mylan to create Viatris.[4][5]
Synthesis
The synthesis of revefenacin was recently reported.[6]
The reaction between 1-benzylpiperidin-4-ol [4727-72-4] (1) and 1-isocyanato-2-phenylbenzene [605-677-1] (2) gave the urethane [171723-80-1]. Next acid transfer hydrogenation cleaved the benzyl protecting group to give [171722-92-2] (3). The reductive amination with Cbz-sarcosinal [107201-33-2] (4). Catalytic hydrogenation then removed the Cbz group to give [743460-48-2] (5). Amide formation with 4-formylbenzoic acid [619-66-9] (6) gave [864760-28-1] (7). Lastly, a reductive amination reaction with isonipecotamide [39546-32-2] (8) completed the synthesis of revefenacin (9).
References
- ↑ "Theravance Biopharma and Mylan Receive FDA Approval for Yupelri (revefenacin) in Adults with Chronic Obstructive Pulmonary Disease" (Press release). Mylan. 9 November 2018. Archived from the original on 15 September 2019. Retrieved 17 January 2019.
- ↑ "Revefenacin: First Global Approval". Drugs 79 (1): 85–91. January 2019. doi:10.1007/s40265-018-1036-x. PMID 30560478.
- ↑ "Efficacy of revefenacin, a long-acting muscarinic antagonist for nebulized therapy, in patients with markers of more severe COPD: a post hoc subgroup analysis". BMC Pulmonary Medicine 20 (1). May 2020. doi:10.1186/s12890-020-1156-4. PMID 32393215.
- ↑ "Pfizer Completes Transaction to Combine Its Upjohn Business with Mylan". Pfizer. 16 November 2020. https://www.businesswire.com/news/home/20201116005378/en/.
- ↑ "Brands". 16 November 2020. https://www.viatris.com/en/products/brands.
- ↑ "Synthetic Approaches to New Drugs Approved during 2018". Journal of Medicinal Chemistry 63 (19): 10652–10704. 8 October 2020. doi:10.1021/acs.jmedchem.0c00345. https://pubs.acs.org/doi/10.1021/acs.jmedchem.0c00345.
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