Antagonists of the human CCR5 receptor as anti-HIV-1 agents. Part 4: synthesis and structure–Activity relationships for 1-[ N-(Methyl)- N-(phenylsulfonyl)amino]-2-(phenyl)-4-(4-( N-(alkyl)- N-(benzyloxycarbonyl)amino)piperidin-1-yl)butanes

Abstract

(2 S)-2-(3-Chlorophenyl)-1-[ N-(methyl)- N-(phenylsulfonyl)amino]-4-[spiro(2,3-dihydrobenzthiophene-3,4′-piperidin-1′-yl)]butane S-oxide ( 1b) has been identified as a potent CCR5 antagonist having an IC 50=10 nM. Herein, structure–activity relationship studies of non-spiro piperidines are described, which led to the discovery of 4-( N-(alkyl)- N-(benzyloxycarbonyl)amino)piperidine derivatives ( 3– 5) as potent CCR5 antagonists.