153260-05-0Relevant articles and documents
A practical synthesis of the PDE4 inhibitor, SB-207499, from a cyclohexanone precursor
Badham, Neil F.,Chen, Jian-Hao,Cummings, Paul G.,Dell'Orco, Philip C.,Diederich, Ann M.,Eldridge, Ann M.,Mendelson, Wilford L.,Mills, Robert J.,Novack, Vance J.,Olsen, Mark A.,Rustum, Abu M.,Webb, Kevin S.,Yang, Shawn
, p. 101 - 108 (2013/09/05)
The synthesis of SB-207499 is described. Investigation and development of new strategies for the homologation of ketone, 4-cyano-4-[3-(cyclopentyloxy)-4-(methoxyphenyl)]-cyclohexan-1-one 2 are described which produce SB-207499. Our ultimate route of synthesis to SB-207499 is robust and operationally simple and produces the final drug substance in good yield and purity.
1,4-Cyclohexanecarboxylates: Potent and selective inhibitors of phosophodiesterase 4 for the treatment of asthma
Christensen, Siegfried B.,Guider, Aimee,Forster, Cornelia J.,Gleason, John G.,Bender, Paul E.,Karpinski, Joseph M.,Dewolf Jr., Walter E.,Barnette, Mary S.,Underwood, David C.,Griswold, Don E.,Cieslinski, Lenora B.,Burman, Miriam,Bochnowicz, Steven,Osborn, Ruth R.,Manning, Carol D.,Grous, Marilyn,Hillegas, Leonard M.,Bartus, Joan O'Leary,Dominic Ryan,Eggleston, Drake S.,Curtis Haltiwanger,Torphy, Theodore J.
, p. 821 - 835 (2007/10/03)
Evaluation of a variety of PDE4 inhibitors in a series of cellular and in vivo assays suggested a strategy to improve the therapeutic index of PDE4 inhibitors by increasing their selectivity for the ability to inhibit PDE4 catalytic activity versus the ability to compete for high affinity [3H]rolipram-binding sites in the central nervous system. Use of this strategy led ultimately to the identification of cis-4-cyano-4-[3- (cyclopentyloxy)-4-methoxyphenyl]cyclohexane-1-carboxylic acid (1, SB 207499, Ariflo(TM)), a potent second-generation inhibitor of PDE4 with a decreased potential for side effects versus the archetypic first generation inhibitor, (R)-rolipram.
Compounds useful for treating allergic and inflammatory diseases
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, (2008/06/13)
Novel compounds of Formula (I) STR1 where X4 is a substituted cyclohexane or cyclohexane group and the other radicals are defined herein. These compounds inhibit the production of Tumor Necrosis Factor and are useful in the treatment of disease states mediated or exacerbated by TNF production. The compounds of the present invention are also useful in the mediation or inhibition of enzymatic or catalytic activity of phosphodiesterase IV and are therefore useful in the treatment of disease states in need of mediation or inhibition thereof.
