Potent heteroarylpiperidine and carboxyphenylpiperidine 1-alkyl-cyclopentane carboxamide CCR2 antagonists

Metal‐Free Efficient, General and Facile Iododecarboxylation Method with Biodegradable Co‐Products

“…Secondary carboxylic acids 14a and 15a can easily be converted into the corresponding synthetically valuable cyclic iodides 13. While clean conversion of piperidine carboxylic acid 14a to the iodide 14b using the Suárez reaction protocol proved to be challenging,14 our method directly provided the desired compound in 87% yield.…”

Chemokine receptor antagonists: Part 1

“…A number of companies have disclosed CCR2 antagonists, including Merck which has been very active in the field reporting CCR2 antagonists in both the peer reviewed [83][84][85][86][87][88][89][90] and the patent literature [91][92][93][94][95][96][97][98] . An extensive Structure Activity Relationship (SAR) approach around a screening hit from the Merck sample collection yielded compound 55, a benzyl piperidine derivative, ( Figure 2 , compound 1) which displays a good binding affinity (IC 50 = 39 nM) in cells expressing recombinant human CCR2 and inhibited CCL2-induced chemotaxis (IC 50 = 9.6 nM) [86] .…”

Fluorine‐Containing sp3‐Enriched Building Blocks for the Multigram Synthesis of Fluorinated Pyrazoles and Pyrimidines with (Hetero)aliphatic Substituents

“…4‐(1‐Methyl‐1 H ‐pyrazol‐3‐yl)piperidine and 4‐(piperidin‐4‐yl)pyrimidine [33] were provided by courtesy of Enamine Ltd. All other starting materials were purchased from commercial sources. Melting points were measured on MPA100 OptiMelt automated melting point system.…”