6,11-Dihydro-11-oxodibenz[b,e]oxepinacetic acids with potent antiinflammatory activity

A series of 6,11-dihydro-11-oxodibenz[b,e]oxepinacetic acids was synthesized and the antiinflammatory activity determined. Studies on 29 compounds revealed certain structure-activity relationships. In the carrageenan edema test, eight compounds exhibited higher antiinflammatory activities than did i...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1976-07, Vol.19 (7), p.941-946
Main Authors: Ueno, Katsujiro, Kubo, Shiro, Tagawa, Hiroaki, Yoshioka, Toshiyuki, Tsukada, Wataru, Tsubokawa, Masao, Kojima, Hiroshi, Kasahara, Akira
Format: Article
Language:English
Subjects:
Acetates - adverse effects
Acetates - chemical synthesis
Acetates - therapeutic use
Animals
Anti-Inflammatory Agents - adverse effects
Anti-Inflammatory Agents - chemical synthesis
Anti-Inflammatory Agents - therapeutic use
Arthritis, Rheumatoid - drug therapy
Dibenzoxepins - adverse effects
Dibenzoxepins - chemical synthesis
Dibenzoxepins - therapeutic use
Edema - drug therapy
Female
Lethal Dose 50
Male
Mice
Rats
Spasm - drug therapy
Stomach Ulcer - chemically induced
Structure-Activity Relationship
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Summary:A series of 6,11-dihydro-11-oxodibenz[b,e]oxepinacetic acids was synthesized and the antiinflammatory activity determined. Studies on 29 compounds revealed certain structure-activity relationships. In the carrageenan edema test, eight compounds exhibited higher antiinflammatory activities than did indomethacin. Several compounds (2, 9, 14, 22, 25) also proved to have activities superior or comparable to indomethacin in suppressing chronic as well as acute inflammation and carrageenan-induced hyperesthesia. Gastric irritation and lethality rates were less frequently observed with these compounds.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00229a017