Nonpeptide arginine vasopressin antagonists for both V(1A) and V2 receptors: Synthesis and pharmacological properties of 2-Phenyl-4'- [(2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)carbonyl]benzanilide derivatives

Article abstract of DOI:10.1248/cpb.45.1870

A series of compounds structurally related to 4'-[(2,3,4,5-tetrahydro- 1H-1-benzazepin-1-yl)carbonyl]benzanilide was synthesized and demonstrated to have arginine vasopressin (AVP) antagonist activity for both V(1A) and V₂ receptors. The introduction of a phenyl or a 4-substituted phenyl group into the ortho position of the benzoyl moiety resulted in an increase in both binding affinity and antagonistic activity. The 2-(4-methylphenyl) derivative (1g) exhibited high antagonistic activities for both V(1A) (8.6- fold) and V₂ (38-fold) receptors and high oral activity (8.6-fold) compared with the 2-methyl lead compound (1a). Detail of the synthesis and the pharmacological properties of this series are presented.

Full text of DOI:10.1248/cpb.45.1870

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