Hey, some of these look pretty easy. Time to go fire up the bunsen burner in my garage.
Preparation of Compound 565
To a solution of 4-oxazolo[4,5-b]pyridin-2-yl pyridine-2-ylamine (0.192 g, 0.91 mmol) in dry pyridine (10 mL) was added TMSC1 (1 mL 0.75 mmol) at 10-15.degree. C. and the reaction mixture was stirred at room temperature for 4 h.
In a separate round bottomed flask, trifluoromethoxy benzoic acid (0.250 g, 1.21 mmol) and thionyl chloride (6 mL) were combined under a nitrogen atmosphere and heated to reflux for 3 h. The excess thionyl chloride was evaporated in vacuo. To this reaction mixture, the above prepared silylated amine was added at room temperature and the mixture was heated to reflux for 6 h. Water (20 mL) was added and the compound was extracted with dichloromethane (2.times.25 mL). The organic layer was dried over anhydrous Na.sub.2SO.sub.4, filtered and concentrated. The crude compound was purified on silica (60-120 mesh) eluted with EtOAc:hexanes, to obtain the pure amide. (Calc'd for C19H11F3N4O3: 400.32, [M+H]+ found: 400.8).
Preparation of Compounds 577, 581, 640, 641 and 668 was done in an analogous manner to Compound 565.
First approved patent regarding the NCEs:
This one is a patent as of 03/17/2008
http://patft.uspto.g...?...&RS=sirtris
Sirtuin modulating compounds
Abstract
Provided herein are novel sirtuin-modulating compounds and methods of use thereof. The sirtuin-modulating compounds may be used for increasing the lifespan of a cell, and treating and/or preventing a wide variety of diseases and disorders including, for example, diseases or disorders related to aging or stress, diabetes, obesity, neurodegenerative diseases, cardiovascular disease, blood clotting disorders, inflammation, cancer, and/or flushing as well as diseases or disorders that would benfit from increased mitochondrial activity. Also provided are compositions comprising a sirtuin-modulating compound in combination with another therapeutic agent.
