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Benzimidazoles as benzamide replacements within cyclohexane-based CC chemokine receptor 2 (CCR2) antagonists. 2012
Robert J Cherney, and
Ruowei Mo, and
Dayton T Meyer, and
Anthony D Pechulis, and
Michael A Guaciaro, and
Yvonne C Lo, and
Gengjie Yang, and
Persymphonie B Miller, and
Peggy A Scherle, and
Qihong Zhao, and
Mary Ellen Cvijic, and
Joel C Barrish, and
Carl P Decicco, and
Percy H Carter
Research and Development, Bristol-Myers Squibb Company, Princeton, NJ 08543-4000, United States. robert.cherney@bms.com
We describe the design, synthesis, and evaluation of benzimidazoles as benzamide replacements within a series of trisubstituted cyclohexane CCR2 antagonists. 7-Trifluoromethylbenzimidazoles displayed potent binding and functional antagonism of CCR2 while being selective over CCR3. These benzimidazoles were also incorporated into lactam-containing antagonists, thus completely eliminating the customary bis-amide.
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