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  • Design, synthesis, and in vivo characterization of a novel series of tetralin amino imidazoles as γ-secretase inhibitors: discovery of PF-3084014.

Design, synthesis, and in vivo characterization of a novel series of tetralin amino imidazoles as γ-secretase inhibitors: discovery of PF-3084014.

Bioorganic & medicinal chemistry letters (2011-01-29)
Michael A Brodney, David D Auperin, Stacey L Becker, Brian S Bronk, Tracy M Brown, Karen J Coffman, James E Finley, Carol D Hicks, Michael J Karmilowicz, Thomas A Lanz, Dane Liston, Xingrong Liu, Barbara-Anne Martin, Robert B Nelson, Charles E Nolan, Christine E Oborski, Christine P Parker, Karl E G Richter, Nikolay Pozdnyakov, Barbara G Sahagan, Joel B Schachter, Sharon A Sokolowski, Barbara Tate, Douglas E Wood, Kathleen M Wood, Jeffrey W Van Deusen, Lei Zhang
ABSTRACT

A novel series of tetralin containing amino imidazoles, derived from modification of the corresponding phenyl acetic acid derivatives is described. Replacement of the amide led to identification of a potent series of tetralin-amino imidazoles with robust central efficacy. The reduction of brain Aβ in guinea pigs in the absence of changes in B-cells suggested a potential therapeutic index with respect to APP processing compared with biomarkers of notch related toxicity. Optimization of the FTOC to plasma concentrations at the brain Aβ EC(50) lead to the identification of compound 14f (PF-3084014) which was selected for clinical development.

MATERIALS
Product Number
Brand
Product Description

Supelco
1,2,3,4-Tetrahydronaphthalene, analytical standard
Sigma-Aldrich
1,2,3,4-Tetrahydronaphthalene, anhydrous, 99%
Sigma-Aldrich
1,2,3,4-Tetrahydronaphthalene, ReagentPlus®, 99%
Sigma-Aldrich
1,2,3,4-Tetrahydronaphthalene, reagent grade, ≥97%