Document Detail


Synthetic study of 2-[(6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9- yl)-sulfinyl]-1H-benzimidazole analogs and their biological properties as novel proton pump inhibitors.
MedLine Citation:
PMID:  7774025     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
A series of 2-[(cycloalka[b]pyridinyl)sulfinyl]-1H-benzimidazoles (11) was synthesized and tested for antisecretory activity against pentagastrin-induced gastric acid secretion in rats. A novel benzimidazole derivative containing a cyclohepta[b]pyridine moiety was found to be the most potent among the congeners, which included five- to eight-membered cycloalka[b]pyridine ring systems. Some 2-[(6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-yl)sulfinyl]-1H- benzimidazole analogs (14) with various substituents on the aromatic rings showed superior properties to omeprazole (1) in biological examinations in vivo. A diastereoisomer, TY-11345 (28Ba), was selected as a promising agent for further evaluation.
Authors:
S Yamada; T Goto; T Yamaguchi; K Aihara; K Kogi; S Narita
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Chemical & pharmaceutical bulletin     Volume:  43     ISSN:  0009-2363     ISO Abbreviation:  Chem. Pharm. Bull.     Publication Date:  1995 Mar 
Date Detail:
Created Date:  1995-07-07     Completed Date:  1995-07-07     Revised Date:  2008-11-21    
Medline Journal Info:
Nlm Unique ID:  0377775     Medline TA:  Chem Pharm Bull (Tokyo)     Country:  JAPAN    
Other Details:
Languages:  eng     Pagination:  421-31     Citation Subset:  IM    
Affiliation:
Fukushima Research Laboratories, Toa Eiyo Ltd., Japan.
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MeSH Terms
Descriptor/Qualifier:
Animals
Anti-Ulcer Agents / chemical synthesis,  chemistry,  pharmacology
Benzimidazoles / chemical synthesis*,  chemistry,  pharmacology*
Chemistry, Physical
H(+)-K(+)-Exchanging ATPase / antagonists & inhibitors
Intestinal Mucosa / drug effects,  secretion
Magnetic Resonance Spectroscopy
Male
Physicochemical Phenomena
Proton Pumps / antagonists & inhibitors*
Rabbits
Rats
Rats, Sprague-Dawley
Stereoisomerism
Structure-Activity Relationship
Chemical
Reg. No./Substance:
0/Anti-Ulcer Agents; 0/Benzimidazoles; 0/Proton Pumps; EC 3.6.1.10/H(+)-K(+)-Exchanging ATPase

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