Pirprofen

Pirprofen Chemische Eigenschaften,Einsatz,Produktion Methoden

• Originator

  Rengasil, Ciba Geigy ,France ,1981

• Verwenden

  Pirprofen is a non-steroidal anti-inflammatory drug.

• Verwenden

  Anti-inflammatory.

• Definition

  ChEBI: Pirprofen is a pyrroline.

• Manufacturing Process

  To the mixture of 85.5 g ethyl α-(3-chloro-4-aminophenyl)-propionate hydrochloride, 142 g sodium carbonate and 600 ml dimethyl formamide, 107g 1,4-dibromo-2-butene are added dropwise while stirring and the whole is refluxed for 5 hours and allowed to stand overnight at room temperature. The mixture is filtered, the filtrate evaporated in vacuo, the residue is triturated with hexane, the mixture filtered, the residue washed with petroleum ether and the filtrate evaporated. The residue is combined with 280 ml 25% aqueous sodium hydroxide and the mixture refluxed for 8 hours. After cooling, it is diluted with water, washed with diethyl ether, the pH adjusted to 5 to 5.2 with hydrochloric acid and extracted with diethyl ether. The extract is dried, filtered, evaporated and the residue crystallized from benzene-hexane, to yield the α-(3-chloro-4-pyrrolinophenyl)-propionic acid melting at 94°C to 96°C.

• Therapeutic Function

  Antiinflammatory

• Weltgesundheitsorganisation (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.

• Handelsname

  Rengasil (Ciba, Greece), Seflenyl (Geigy, Argentina).

• Clinical Use

  Pirprofen has been used to treat rheumatoid arthritis, osteoarthritis, and ankylosing spondylitis. An optimal dosing regimen of 200 mg three times a day has been developed for maximal activity with minimal adverse effects. Pirprofen also is effective in relieving pain from malignant disease and oral surgery.

• Synthese

  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.
  

Pirprofen Upstream-Materialien And Downstream Produkte

Pirprofen Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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