253168-91-1Relevant academic research and scientific papers
Discovery of (S)-N-{2-[1-(3-ethoxy-4-methoxy-phenyl)-2- methanesulfonylethyl]-1,3-dioxo-2,3-dihydro-1 H-isoindol-4-yl}acetamide (Apremilast), a potent and orally active phosphodiesterase 4 and tumor necrosis factor-a inhibitor
Man, Hon-Wah,Schafer, Peter,Wong, Lu Min,Patterson, Rebecca T.,Corral, Laura G.,Raymon, Heather,Blease, Kate,Leisten, Jim,Shirley, Michael A.,Tang, Yang,Babusis, Darius M.,Chen, Roger,Stirling, Dave,Muller, George W.
body text, p. 1522 - 1524 (2010/01/16)
In this communication, we report the discovery of 1S (apremilast), a novel potent and orally active phosphodiesterase 4 (PDE4) and tumor necrosis factor-α inhibitor. The optimization of previously reported 3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-3-(3,4-dimethoxyphenyl)propionic acid PDE4 inhibitors led to this series of sulfone analogues. Evaluation of the structure-activity relationship of substitutions on the phthalimide group led to the discovery of an acetylamino analogue 1S, which is currently in clinical trials.
Substituted phenethylsulfones and method of reducing TNF alpha levels
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, (2008/06/13)
Phenethylsulfones substituted in the position alpha to the phenyl group with a 1-oxoisoindoline or 1,3-dioxoisoindoline group reduce the levels of TNF alpha in a mammal. Typical embodiments are 2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-aminoisoindoline-1,3-dione and 2-[1-(3-cyclopentyloxy-4-methoxyphenyl)-2-methylsulfonylethyl]isoindoline-1,3-dione.
