129719-64-8Relevant articles and documents
Discovery and development of an efficient process to atovaquone
Britton, Hugh,Catterick, David,Dwyer, Andrew N.,Gordon, Andrew H.,Leach, Stuart G.,McCormick, Chris,Mountain, Clive E.,Simpson, Alec,Stevens, David R.,Urquhart, Michael W. J.,Wade, Charles E.,Warren, John,Wooster, Nick F.,Zilliox, Audrey
, p. 1607 - 1617 (2013/02/23)
The discovery and development of an efficient and more sustainable manufacturing route to the antipneumocystic agent atovaquone (2-((1R,4R)-4-(4-chlorophenyl)cyclohexyl)-3-hydroxynaphthalene-1,4-dione) 1 is described. The existing commercial route to atovaquone delivers a poor yield of product and uses expensive reagents. The new synthesis commences with readily available phthalic anhydride, which is converted to 1,4-isochromandione 5 and then to atovaquone 1 by reaction with 4-(4-chlorophenyl)cyclohexanecarboxylic acid 3 using key bromination, Rosenmund reduction, and rearrangement chemistries. Downstream processing to atovaquone is both high yielding and robust, and the resulting process has been demonstrated on 200-kg scale. The process is simple, uses cheap raw materials, and is more sustainable in that it avoids lowyielding silver-promoted chemistry and isomerisation procedures. It includes a robust, facile, and highly efficient procedure to 1,4-isochromandione 5, and routes to 4-(4-chlorophenyl)cyclohexanecarboxaldehyde 9 have also been developed, including a Rosenmund method that was demonstrated on pilot-plant scale. Also discussed are the route-derived impurities and processing amendments to control their formation.
PROCESS FOR PREPARATION OF ATOVAQUONE AND THE CONVERSION OF CIS-ISOMER TO TRANS- ISOMER
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Page/Page column 11; 12, (2008/12/04)
Substantially pure atovaquone and parocess for the preparation thereof is disclosed.
Method for treating animals infected with Babesia spp.
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, (2008/06/13)
The present invention relates to pharmaceutical compositions for the treatment and/or prophylaxis of protozoal infections caused by Kinetoplastida, Apicomplexa, Anaerobic protozoa and Mircosporidia comprising 2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthoquinone or a physiologically acceptable salt or other functional derivative thereof as active ingredient and to a method of treating or preventing siad protozoal infections in an animal which comprises administering to said animal an effective amount of siad compound.