Cc1cccc(CN2CCC(C#N)CC2)c1
I like fragment 0692 because it has nice interactions in the active site around Met49. I assume the methylketone is the warhead and the catalytic Cys145 attacks on the carbon of the ketone, although this is not completely correctly modelled in the X-ray structure. My first step would be to replace the ketone warhead with a more drug-like warhead. A nitrile is an excellent choice, since this is the warhead of odanacatib, an MSD CatK inhibitor (also cys-protease) that made it all the way to Phase III clinical trials.
As groupleader in Organon/Schering-Ploug/MSD, I worked for many years on Cathepsin K and Cathepsin S inhibitors and you'll find me as co-author on several publications and PDB entries on these targets. Between 2010-2011, I worked on the Odanacatib project of MSD. NB the piperidine-nitrile is available as building block from Sigma 696447-1G