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

DOI: 10.1248/cpb.47.329

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 329 - 339 (1999)

Update date:2022-08-05

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Authors:

Matsuhisa, Akira

Kikuchi, Kazumi

Sakamoto, Kenichiro

Yatsu, Takeyuki

Tanaka, Akihiro

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Article abstract of DOI:10.1248/cpb.47.329

Arginine vasopressin (AVP) has a dual action, i.e. vasoconstriction and water reabsorption via V(1A) and V₂ receptors, and may play a role in a number of diseases, including congestive heart failure (CHF), hypertension, renal disease, edema, and hyponatremia. We have attempted to develop a new series of AVP antagonists for both V(1A) and V₂ receptors based on the hypothesis that the blockade of both V(1A) and V₂ receptors might be beneficial to CHF patients. In this report, a series of compounds structurally related to 4'-[5-(substituted methylidene)2,3,4,5-tetrahydro- 1H-1-benzoazepine-1-carbonyl]benzanilide (exo-olefin isomer) and 4'-[5- (substituted methyl)2,3-dihydro-1H-1-benzoazepine-1-carbonyl]benzanilide (endo-olefin isomer) were synthesized and examined to have AVP antagonist activity for both V(1A) and V₂ receptors. As a result, it was found that the (E)-exo-olefin isomers showed more potent binding affinity compared with endo-olefin isomers. Among these (E)-exo-olefin isomers, (E)-N-methyl-{1- [4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzoazepin-5- ylidene}ac-etamide (14) exhibited the most potent binding affinitiy and (E)- N-methyl-(1-{4-12-(4'methylphenyl)benzoyl-amino]benzoyl}-2,3,4,5- tetrahydro-1H-1-benzoazepin-5-ylidene)acetamide (20) exhibited a high AVP antagonist activity for both V(1A) and V₂ receptors after intravenous administration. Details of the synthesis and pharmacological properties of this series are presented.

Full text of DOI:10.1248/cpb.47.329

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DOI: 10.1248/cpb.47.329