4,10-dihydro-5H-thieno[3,2-c][1]benzazepine derivatives and 9,10-dihydro-4H-thieno[2,3-c][1]benzazepine derivatives as orally active arginine vasopressin receptor antagonists

V Aranapakam; J D Albright; G T Grosu; P S Chan; J Coupet; T Saunders; X Ru; H Mazandarani

doi:10.1016/s0960-894x(99)00278-4

4,10-dihydro-5H-thieno[3,2-c][1]benzazepine derivatives and 9,10-dihydro-4H-thieno[2,3-c][1]benzazepine derivatives as orally active arginine vasopressin receptor antagonists

Bioorg Med Chem Lett. 1999 Jul 5;9(13):1733-6. doi: 10.1016/s0960-894x(99)00278-4.

Authors

V Aranapakam¹, J D Albright, G T Grosu, P S Chan, J Coupet, T Saunders, X Ru, H Mazandarani

Affiliation

¹ Wyeth-Ayerst Research, Pearl River, NY 10965, USA.

PMID: 10406632
DOI: 10.1016/s0960-894x(99)00278-4

Abstract

Synthesis and structure-activity relationships (SAR) of arginine vasopressin receptor (AVP) antagonists are described. Potent and orally active compounds are prepared when tricyclic 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine moiety in VPA-985 1 is replaced with a compound 7 or 12.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Administration, Oral
Animals
Antidiuretic Hormone Receptor Antagonists*
Azepines / chemical synthesis*
Azepines / pharmacology*
Benzamides / chemical synthesis*
Benzamides / pharmacology*
Benzazepines / chemical synthesis*
Benzazepines / pharmacology
Fibroblasts
Inhibitory Concentration 50
Mice
Pyrroles
Structure-Activity Relationship
Thiophenes / chemical synthesis*
Thiophenes / pharmacology

Substances

5-(((2-chloro-4-(5-fluoro-2-methylphenyl)carbonylamino)phenyl)carbonyl)-9,10-dihydro-4H-thieno(2,3-c)(1)benzazepine
5-((4-((2-methylphenyl)carbonylamino)phenyl)carbonyl)-4,10-dhydro-5H-thieno(3,2-c)(1)benzazepine
Antidiuretic Hormone Receptor Antagonists
Azepines
Benzamides
Benzazepines
Pyrroles
Thiophenes
lixivaptan