On June 27, 2002, Li, Guiying; Peterson, John M.; Albaugh, Pamela; Currie, Kevin S.; Cai, Guolin; Gustavson, Linda M.; Lee, Kyungae; Hutchison, Alan; Singh, Vinod; Maynard, George D.; Yuan, Jun; Ling, Hong Xie; Ghosh, Manuka; Liu, Nian; Luke, George P.; Mitchell, Scott; Allen, Martin Patrick; Liras, Spiros published a patent.Reference of 3-Chloro-4-nitrobenzonitrile The title of the patent was Aryl or heteroaryl fused imidazoles as selective GABAA receptor ligands. And the patent contained the following:
Title compounds I [W = N or CR3, X = N or CR4, Y = N or CR5, Z = N or CR6 with the provision that no more than two of W, X, Y and Z are N; Q = O or CR7R8; R1 = H, haloalkyl, (un)substituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl, arylalkyl, heteroaryl, etc.; R2 = nitrogen containing 5-7 membered (un)substituted heteroaryl or heterocycloalkyl ring with up to 4 heteroatoms independently selected from N, S, and O; R3, R4, R5 and R6 are independently selected from H, halo, OH, NO2, CN, (un)substituted alkyl, alkoxy, etc.] and there pharmaceutically acceptable salts are prepared and disclosed as selective GABAA receptor ligands. Thus, II was prepared in five steps from malonyl dichloride and Et vinyl ether with imidazole ring formation via cyclocondensation of 3-amino-4-ethylaminobenzonitrile with 1-(3-fluorophenyl)-5-carboxymethylpyrazole. The invention is particularly related to such compounds that bind with high selectivity and high affinity to the benzodiazepine site of GABAA receptors. Preferred compounds of the invention exhibit Ki values of < 100 nM for binding at the benzodiazepine site with more preferred compounds exhibiting Ki values of < 10 nM. This invention also relates to pharmaceutical compositions comprising such compounds and to the use of such compounds in treatment of certain central nervous system (CNS) diseases. This invention also relates to the use of I in combination with one or more other CNS agents to potentiate the effects of the other CNS agents. Addnl. this invention relates to the use such compounds as probes for the localization of GABAA receptors in tissue sections. The experimental process involved the reaction of 3-Chloro-4-nitrobenzonitrile(cas: 34662-29-8).Reference of 3-Chloro-4-nitrobenzonitrile
The Article related to imidazole aryl preparation gaba receptor ligand cns agent, Heterocyclic Compounds (More Than One Hetero Atom): Imidazoles and other aspects.Reference of 3-Chloro-4-nitrobenzonitrile
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts