Document Detail

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.
MedLine Citation:
PMID:  9810694     Owner:  NLM     Status:  MEDLINE    
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.
A Matsuhisa; H Koshio; K Sakamoto; N Taniguchi; T Yatsu; A Tanaka
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Publication Detail:
Type:  In Vitro; Journal Article    
Journal Detail:
Title:  Chemical & pharmaceutical bulletin     Volume:  46     ISSN:  0009-2363     ISO Abbreviation:  Chem. Pharm. Bull.     Publication Date:  1998 Oct 
Date Detail:
Created Date:  1998-12-11     Completed Date:  1998-12-11     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0377775     Medline TA:  Chem Pharm Bull (Tokyo)     Country:  JAPAN    
Other Details:
Languages:  eng     Pagination:  1566-79     Citation Subset:  IM    
Institute for Drug Discovery Research, Yamanouchi Pharmaceutical Co., Ltd., Ibaraki, Japan.
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MeSH Terms
Anilides / chemical synthesis*,  pharmacokinetics,  pharmacology
Arginine Vasopressin / antagonists & inhibitors*
Biological Availability
Indoles / chemical synthesis*,  pharmacokinetics,  pharmacology
Magnetic Resonance Spectroscopy
Pyrrolidines / chemical synthesis*,  pharmacokinetics,  pharmacology
Receptors, Oxytocin / drug effects,  metabolism
Receptors, Vasopressin / antagonists & inhibitors*
Reg. No./Substance:
0/Anilides; 0/Indoles; 0/Pyrrolidines; 0/Receptors, Oxytocin; 0/Receptors, Vasopressin; 113-79-1/Arginine Vasopressin; 150375-75-0/relcovaptan

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