N-Substituted dibenzoxazepines as analgesic PGE2 antagonists

8-Chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, 2-acetylhydrazide (1, SC-19220) has been previously reported by us and others to be a PGE2 antagonist selective for the EP1 receptor subtype with antinociceptive activities. Analogs of SC-19220, in which the acetyl moiety has been replaced w...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1993-10, Vol.36 (22), p.3293-3299
Main Authors: Hallinan, E. Ann, Hagen, Timothy J, Husa, Robert K, Tsymbalov, Sofya, Rao, Shashidhar N, vanHoeck, Jean Pierre, Rafferty, Michael F, Stapelfeld, Awilda, Savage, Michael A, Reichman, Melvin
Format: Article
Language:English
Subjects:
Analgesics - chemical synthesis
Analgesics - pharmacology
Animals
Chemical Phenomena
Chemistry
Chemistry, Physical
Dibenz(b,f)(1,4)oxazepine-10(11H)-carboxylic acid, 8-chloro-, 2-acetylhydrazide - analogs & derivatives
Dibenzoxazepines - chemical synthesis
Dibenzoxazepines - pharmacology
Dinoprostone - antagonists & inhibitors
Exact sciences and technology
Guinea Pigs
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
In Vitro Techniques
Male
Mice
Mice, Inbred Strains
Nociceptors - drug effects
Organic chemistry
Preparations and properties
Solubility
Structure-Activity Relationship
Water
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Description
Summary:8-Chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, 2-acetylhydrazide (1, SC-19220) has been previously reported by us and others to be a PGE2 antagonist selective for the EP1 receptor subtype with antinociceptive activities. Analogs of SC-19220, in which the acetyl moiety has been replaced with pyridylpropionyl groups and their homologs, have been synthesized as illustrated by compounds 13 and 29. These and other members of this series have been shown to be efficacious analgesics and PGE2 antagonists of the EP1 subtype. This report discusses the structure activity relationships within this series.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00074a010