Synthesis and pharmacological properties of N-[4-[4-(1H-indol-3-yl) piperidinoalkyl]-2-thiazolyl]alkanesulfonamides as novel antiallergic agents

Chem Pharm Bull (Tokyo). 1993 Sep;41(9):1589-95. doi: 10.1248/cpb.41.1589.

Abstract

A number of N-[4-[4-(1H-indol-3-yl)piperidinoalkyl]-2- thiazolyl]alkanesulfonamides (8--21) were synthesized and evaluated for their preventive effects on systemic anaphylaxis in guinea pigs. Structure-activity analysis revealed that methane- and ethanesulfonamide derivatives having a one to three methylene tether between the piperidine and thiazole rings exhibited potent activity but the introduction of a substituent on the indole part reduced the activity. Administration (100 mg/kg p.o.) of the four compounds 8, 9, 12, 13, together with ketotifen, oxatomide, terfenadine and azelastine as reference compounds, to mice revealed that only compound 8 caused no significant increase of the sleeping time induced by hexobarbital. In addition, compound 8 (10 mg/kg i.v.) did not change the electroencephalogram in conscious rabbits. These results led to the selection of N-[4-[4-(1H-indol-3-yl)piperidinomethyl]-2-thiazolyl]methanesulfon amide (8, FK613) for further development as a novel antiallergic agent. Clinical evaluation of FK613 is now in progress.

MeSH terms

  • Anaphylaxis / drug therapy
  • Animals
  • Guinea Pigs
  • Hypersensitivity / drug therapy*
  • Indoles / chemical synthesis*
  • Indoles / pharmacology
  • Male
  • Mice
  • Mice, Inbred ICR
  • Ovalbumin / immunology
  • Rabbits
  • Structure-Activity Relationship
  • Sulfonamides / chemical synthesis*
  • Sulfonamides / pharmacology
  • Thiazoles / chemical synthesis*
  • Thiazoles / pharmacology

Substances

  • Indoles
  • Sulfonamides
  • Thiazoles
  • Ovalbumin