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A series of compounds structurally related to 2-phenyl-4'-(2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-carbonyl) benzanilide was synthesized and demonstrated to have arginine vasopressin (AVP) antagonist activity for both V1A and V2 receptors. The introduction of a hydrophilic substituent group into the 5-position of the benzodiazepine ring resulted in an increase in oral availability. Especially, the (3-pyridyl)methyl (31b), the 2-(4-methyl-1,4-diazepan-1-yl)-2-oxoethyl (32i), and the 2-(4-methylpiperazin-1-yl)ethyl (33g) derivatives exhibited high antagonist activities and high oral availability. Details of the synthesis and pharmacological properties of this series are presented.

chemical and pharmaceutical bulletin/chemical and pharmaceutical bulletin

Nonpeptide Arginine Vasopressin Antagonists for Both V1A and V2 Receptors: Synthesis and Pharmacological Properties of 2-Phenyl-4'-(2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-carbonyl)benzanilide Derivatives.