On January 30, 2014, Wang, Yansong; Hausch, Felix published a patent.Reference of Ethyl 6-cyanopicolinate The title of the patent was Preparation of bicyclic aza-amides for treatment of psychiatric disorders. And the patent contained the following:
The invention relates to bicyclic aza-amides of formula I as inhibitors of FK506 binding proteins (FKBP) useful in the prophylaxis and/or treatment of psychiatric, neurodegenerative diseases. Compounds of formula I wherein X is CH2, CH2CH2, CH(CH=CH2), etc.; R1 is H, Me, Et, etc.; R2 is substituted Ph, substituted cyclohexyl, substituted pyridyl, etc. and enantiomers, stereoisomeric forms, mixtures of enantiomers, anomers, deoxyforms, diastereomers, mixtures of diastereomers, prodrugs, tautomers, hydrates, solvates and racemates of the above mentioned compounds, are claimed. Example compound II was prepared by alkylation of benzyl 2-oxo-3,9-diazabicyclo[3.3.1]nonane-9-carboxylate with 4-(2-bromoethoxy)-1,2-dimethoxybenzene; the resulting benzyl 3-(2-(3,4-dimethoxyphenoxy)ethyl)-2-oxo-3,9-diazabicyclo[3.3.1]nonane-9-carboxylate underwent Cbz-deprotection followed by sulfonylation with 3,5-dichlorobenzene sulfonyl chloride. The invention compounds were evaluated for their FKBP binding affinity in which II inhibited FKBP51 and FKBP52 with an IC50 of 1.3±0.13 μM and 2.5±0.38 μM, resp. From the assay, it was determined that example II exhibited IC50 value of 12.2±3.7 μM, 8.8±1.1 μM and 0.14±0.01 μM towards FKBP52, FKBP51 and FKBP12, resp. The experimental process involved the reaction of Ethyl 6-cyanopicolinate(cas: 97483-79-9).Reference of Ethyl 6-cyanopicolinate
The Article related to bicyclic aza amide preparation fkbp inhibitor psychiatric neurol disease, Heterocyclic Compounds (One Hetero Atom): Pyridines and other aspects.Reference of Ethyl 6-cyanopicolinate