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    J Med Chem. 2005 Dec 1;48(24):7882-905.

    Discovery and development of a new class of potent, selective, orally active oxytocin receptor antagonists.

    Source

    Serono Pharmaceutical Research Institute, Departments of Chemistry and Biochemical Pharmacology, 14 Chemin des Aulx, 1228 Plan-Les-Ouates, Geneva, Switzerland.

    Abstract

    We report a novel chemical class of potent oxytocin receptor antagonists showing a high degree of selectivity against the closely related vasopressin receptors (V1a, V1b, V2). An initial compound, 7, was shown to be active in an animal model of preterm labor when administered by the intravenous but not by the oral route. Stepwise SAR investigations around the different structural elements revealed one position, the arenesulfonyl moiety, to be amenable to structural changes. Consequently, this position was used to introduce a variety of substituents to improve the physicochemical properties. Some of the resulting analogues were found to be superior to 7 both in terms of potency in vitro and aqueous solubility, which translated into significantly improved efficacy in the animal model after intravenous and oral administration. The best compound, 73, potently inhibited oxytocin-induced uterine contractions in nonpregnant rats and reduced spontaneous uterine contractions in late-term pregnant rats.

    PMID:
    16302826
    [PubMed - indexed for MEDLINE]

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