Synthesis and evaluation of 4,6-disubstituted pyrimidines as CNS penetrant pan-muscarinic antagonists with a novel chemotype

合成和评价具有新型化学类型的4,6-二取代嘧啶类化合物作为中枢神经系统穿透性泛毒蕈碱拮抗剂

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Abstract

This letter describes the synthesis and structure activity relationship (SAR) studies of structurally novel M(4) antagonists, based on a 4,6-disubstituted core, identified from a high-throughput screening campaign. A multi-dimensional optimization effort enhanced potency at both human and rat M(4) (IC(50)s<300nM), with no substantial species differences noted. Moreover, CNS penetration proved attractive for this series (brain:plasma K(p,uu)=0.87), while other DMPK attributes were addressed in the course of the optimization effort, providing low in vivo clearance in rat (CL(p)=5.37mL/min/kg). Surprisingly, this series displayed pan-muscarinic antagonist activity across M(1-5), despite the absence of the prototypical basic or quaternary amine moiety, thus offering a new chemotype from which to develop a next generation of pan-muscarinic antagonist agents.

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