N-(Methanesulfonyl)-16-phenoxyprostaglandincarboxamides: tissue-selective, uterine stimulants

In an effort to develop tissue-selective prostaglandin analogues resistant to the metabolic inactivating pathways of the natural materials, hybrid compounds modified both at C-1 with a sulfonimide moiety and in the n-amylcarbinol side chain with substituted phenoxy groups were synthesized and evalua...

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Veröffentlicht in:	Journal of medicinal chemistry 1981-11, Vol.24 (11), p.1353-1359
Hauptverfasser:	Schaaf, T K, Bindra, J S, Eggler, J F, Plattner, J J, Nelson, A J, Johnson, M R, Constantine, J W, Hess, H J, Elger, W
Format:	Artikel
Sprache:	eng
Schlagworte:	Abortifacient Agents, Nonsteroidal - chemical synthesis Animals Chemical Phenomena Chemistry Female Guinea Pigs Haplorhini Hydroxyprostaglandin Dehydrogenases - antagonists & inhibitors In Vitro Techniques Lung - enzymology Organ Specificity Pregnancy Prostaglandins, Synthetic - chemical synthesis Prostaglandins, Synthetic - pharmacology Stimulation, Chemical Structure-Activity Relationship Uterine Contraction - drug effects
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Beschreibung
Zusammenfassung:	In an effort to develop tissue-selective prostaglandin analogues resistant to the metabolic inactivating pathways of the natural materials, hybrid compounds modified both at C-1 with a sulfonimide moiety and in the n-amylcarbinol side chain with substituted phenoxy groups were synthesized and evaluated in a variety of in vitro models. Several of these analogues exhibited potent, tissue-selective, uterine stimulant activity, a finding subsequently confirmed in clinical studies with one member of this series, N-(methanesulfonyl)-16-phenoxy-omega-tetranor-PGE2-carboxamide (CP-34089/ZK-57671, sulprostone).
ISSN:	0022-2623
DOI:	10.1021/jm00143a018