Invention Grant
US07888337B2 Synthesis of oseltamivir containing phosphonate congeners with anti-influenza activity
有权
含有具有抗流感活性的膦酸酯同系物的奥司他韦的合成
- Patent Title: Synthesis of oseltamivir containing phosphonate congeners with anti-influenza activity
- Patent Title (中): 含有具有抗流感活性的膦酸酯同系物的奥司他韦的合成
-
Application No.: US12201955Application Date: 2008-08-29
-
Publication No.: US07888337B2Publication Date: 2011-02-15
- Inventor: Chi-Huey Wong , Jim-Min Fang , Jiun-Jie Shie , Yih-Shyun Edmond Cheng , Jia-Tsrong Jan
- Applicant: Chi-Huey Wong , Jim-Min Fang , Jiun-Jie Shie , Yih-Shyun Edmond Cheng , Jia-Tsrong Jan
- Applicant Address: TW Taipei
- Assignee: Academia Sinica
- Current Assignee: Academia Sinica
- Current Assignee Address: TW Taipei
- Agency: Occhiuti Rohlicek & Tsao LLP
- Main IPC: A61K31/66
- IPC: A61K31/66

Abstract:
Novel phosphonate compounds are described. The compounds have activity as neuraminidase inhibitors against wild-type and H274Y mutant of H1N1 and H5N1 viruses. The present disclosure also provides an enantioselective synthetic route to known neuraminidase inhibitors oseltamivir and the anti-flu drug Tamiflu®, as well as novel phosphonate compounds, via D-xylose. Another efficient and flexible synthesis of Tamiflu and the highly potent neuraminidase inhibitor Tamiphosphor was also achieved in 11 steps and >20% overall yields from the readily available fermentation product (1S-cis)-3-bromo-3,5 -cyclohexadiene-1,2-diol. Most of the reaction intermediates were obtained as crystals without tedious purification procedures. The key transformations include an initial regio- and stereoselective bromoamidation of a bromoarene cis-dihydrodiol, as well as the final palladium-catalyzed carbonylation and phosphonylation.
Public/Granted literature
- US20100113397A1 SYNTHESIS OF OSELTAMIVIR CONTAINING PHOSPHONATE CONGENERS WITH ANTI-INFLUENZA ACTIVITY Public/Granted day:2010-05-06
Information query