Darcsi András, Tóth Gergő, Kökösi József, Béni Szabolcs
Department of Pharmaceutical Chemistry, Semmelweis University, Hőgyes Endre Street 9, H-1092 Budapest, Hungary.
Department of Pharmaceutical Chemistry, Semmelweis University, Hőgyes Endre Street 9, H-1092 Budapest, Hungary.
J Pharm Biomed Anal. 2014 Aug 5;96:272-7. doi: 10.1016/j.jpba.2014.04.002. Epub 2014 Apr 13.
Unknown by-product associated with the synthesis of dapoxetine was isolated. The structure elucidation of this new compound using accurate mass data and NMR spectroscopy is presented herein. The unambiguous resonance assignment concluded to the formation of a tricyclic compound 4-phenyl-2H,3H,4H-naphtho[1,2-b]pyran, a new impurity of dapoxetine which has never been reported previously. A proposed mechanism for the formation of the new carbon-carbon bond is discussed. For the separation of dapoxetine and the process-related impurities, a gradient HPLC method was developed.
分离出了与达泊西汀合成相关的未知副产物。本文介绍了使用精确质量数据和核磁共振光谱对这种新化合物进行结构解析的过程。明确的共振归属确定形成了一种三环化合物4-苯基-2H,3H,4H-萘并[1,2-b]吡喃，这是达泊西汀一种新的杂质，此前从未有过报道。讨论了新碳-碳键形成的可能机制。为了分离达泊西汀和与工艺相关的杂质，开发了一种梯度高效液相色谱法。
