Trovafloxacin

The acid undergoes a version of the Curtius rearrangement when treated with diphenylphosphoryl azide (DPPA) to afford the transient isocyanate (6).

The reactive function adds t-BuOH from the reaction medium to afford the product as its tert-Butyloxycarbonyl protecting group derivative (7).

[4] In June 1999, the agency advised doctors to limit the prescription of trovafloxacin due to adverse events associated with the drug (over 100 cases of acute liver injury reported to FDA).

[5] In June 1999, in view of reported adverse events, the Committee for Proprietary Medicinal Products recommended suspension of the marketing authorisation for a year.

[5] In October 2000, Pfizer notified the European Commission of its decision to voluntarily withdraw the marketing authorisation which was approved by EMA in March 2001.

Others suffered blindness, deafness and brain damage, common consequences of meningitis that have not been seen in patients treated with trovafloxacin for other infection types.

[10][11][12] An investigation by the Washington Post concluded that Pfizer had administered the drug as part of an illegal clinical trial without authorization from the Nigerian government or consent from the children's parents.

Trovafloxacin synthesis: K. E. Brighty, U.S. patent 5,164,402 (1992 to Pfizer).