Synthesis and antiinflammatory activity of 6,11-dihydro-11-oxodibenzo[b,e]thiepinalkanoic acids and related compounds

J Med Chem. 1978 Oct;21(10):1035-44. doi: 10.1021/jm00208a007.

Abstract

Acetic acid derivatives of tricyclic systems, such as 6,11-dihydro-11-oxodibenzo[b,e]thiepin, 4,10-dihydro-4-oxo-thieno[2,3-c][1]benzothiepin, dibenzo[b,f]thiepin, dibenz[b,f]oxepin, etc., were synthesized and assayed for antiinflammatory activity. One of the compounds, 6,11-dihydro-11-oxodibenzo[b,e]thiepin-3-acetic acid (52), was chosen for evaluation in man on the basis of high antiinflammatory activity in both short- and long-term animal assays and a low gastric irritation liability in rats and dogs.

MeSH terms

  • Acetates / chemical synthesis
  • Acetates / pharmacology
  • Animals
  • Anti-Inflammatory Agents / chemical synthesis*
  • Anti-Inflammatory Agents, Non-Steroidal / chemical synthesis
  • Arthritis, Experimental / physiopathology
  • Carrageenan
  • Chemical Phenomena
  • Chemistry
  • Dibenzothiepins / chemical synthesis*
  • Dibenzothiepins / pharmacology
  • Dogs
  • Edema / physiopathology
  • Female
  • Gossypium
  • Granuloma / physiopathology
  • Male
  • Mice
  • Quinones / antagonists & inhibitors
  • Rats
  • Stomach Ulcer / chemically induced
  • Structure-Activity Relationship

Substances

  • Acetates
  • Anti-Inflammatory Agents
  • Anti-Inflammatory Agents, Non-Steroidal
  • Dibenzothiepins
  • Quinones
  • Carrageenan