Nitrogen-containing heteroalicycles with serotonin receptor binding affinity: development of gastroprokinetic and antiemetic agents

Med Res Rev. 1999 Jan;19(1):25-73. doi: 10.1002/(sici)1098-1128(199901)19:1<25::aid-med3>3.0.co;2-e.

Abstract

To obtain gastroprokinetic agents with more potent and selective activity than metoclopramide and cisapride, a series of N-(4-benzyl-2-morpholinylmethyl)benzamides were designed and prepared. Their synthesis and structure-activity relationships were described. As a result, mosapride was selected as a promising candidate for potent gastroprokinetic activity with selective 5-HT4 receptor agonistic activity. As an extension to this project, the novel benzamide and the carboxamide derivatives having 1-benzyl-4-methylhexahydro-1,4-diazepine ring in the amine moiety were prepared and evaluated for 5-HT3 receptor antagonistic activity. DAT-582 was identified as an antiemetic agent in cancer chemotherapy. The asymmetric synthesis of DAT-582 and the SAR studies were briefly reviewed. In further modifications of the N-(1-benzyl-4-methylhexahydro-1,4-diazepin-6-yl)benzamides, the novel nicotinamides with 1-ethyl-4-methylhexahydro-1,4-diazepin ring were found to have potent 5-HT3 and dopamine D2 and D3 receptor antagonistic activities and to show weak central nervous system depression and extrapyramidal syndrome. After extensive SARs, AS-8112 was selected as a broad antiemetic agent.

Publication types

  • Review

MeSH terms

  • Animals
  • Antiemetics / chemical synthesis
  • Antiemetics / metabolism*
  • Antiemetics / pharmacology
  • Drug Design
  • Gastrointestinal Agents / chemical synthesis
  • Gastrointestinal Agents / metabolism*
  • Gastrointestinal Agents / pharmacology
  • Molecular Structure
  • Receptors, Serotonin / metabolism*
  • Serotonin Antagonists / chemical synthesis
  • Serotonin Antagonists / metabolism
  • Serotonin Antagonists / pharmacology
  • Structure-Activity Relationship

Substances

  • Antiemetics
  • Gastrointestinal Agents
  • Receptors, Serotonin
  • Serotonin Antagonists