Pirprofen

Pirprofen 화학적 특성, 용도, 생산

• 용도

  Pirprofen is a non-steroidal anti-inflammatory drug.

• World Health Organization (WHO)

  Pirprofen, a nonsteroidal anti-inflammatory agent, was introduced in 1982 primarily for the treatment of rheumatic diseases, as well as for use in posttraumatic and post-operative inflammatory conditions, acute gout and dysmenorrhoea. Reports of serious adverse effects, in particular cases of liver toxicity, some of which were fatal, led the manufacturer, in 1985 and in 1989, to amend the approved product information of the drug, limiting duration of treatment and lowering the recommended doses. In the light of these successive restrictions, which have considerably reduced the field of application of pirprofen and in view of available alternatives, the manufacturer has decided to discontinue the drug worldwide.

• Synthesis

  Synthesis: treatment of the sodium salt of diethyl methylmalonate with 2,4- dichloronitrobenzene yields diethyl (3-chloro- 4-nitrophenyl)methylmalonate. Saponification, decarboxylation, and subsequent reesterification followed by catalytic reduction gives ethyl 4-amino-3-chloro-α-methylbenzeneacetate hydrochloride. Treatment of the latter with 1,4- dichloro-2-butene in the presence of sodium carbonate followed by saponification affords pirprofen.
  

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