On January 31, 2008, Efremov, Ivan Viktorovich; Rogers, Bruce Nelsen; Duplantier, Allen Jacob; Zhang, Lei; Zhang, Qian; Maklad, Noha Serour; Evrard, Edelweiss Virginie; Brodney, Michael A. published a patent.Formula: C7H3ClN2O2 The title of the patent was Benzimidazolyl compounds as potentiators of mGluR2 subtype of glutamate receptor and their preparation, pharmaceutical compositions and use in the treatment of diseases. And the patent contained the following:
Compounds and pharmaceutically acceptable salts of the compounds are disclosed, wherein the compounds have the structure of formula I as defined in the specification. Corresponding pharmaceutical compositions, methods of treatment, methods of synthesis, and intermediates are also disclosed. Compounds of formula I wherein X1 is CR7; X2 is CR4; X3 is CR6; X4 is (CHR9)0-2; X5 is CH2, CH2CH2; X8 is CR3; R1, R2, R3, R4 and R6 are independently H, halo, CN, OH and derivatives, alkyl, alkenyl, etc.; R7 is H, halo, OH, alkyl, alkoxy, CN and alkyl-CO; R5, R8 and R9 are independently halo, CN, OH and derivatives, CO2H and derivatives, NH2 and derivatives, H, alkyl, alkenyl, etc.; R11, R12, R13 and R14 are independently halo, CN, H, CO2H and derivatives, CONH2 and derivatives, OH and derivatives, NH2 and derivatives, alkyl, etc.; R17 is (un)substituted alkyl, (un)substituted alkenyl, (un)substituted cycloalkyl, and (un)substituted cycloalkenyl; R18 is H, halo and alkyl; R19 are H; R8R19 taken together to form =O; and their pharmaceutically acceptable salts thereof, are claimed. Example compound II•HCl was prepared by reductive alkylation of 4-(2-methoxy-4-trifluoromethylphenyl)piperidine hydrochloride with 1-methyl-1H-benzo[d]imidazole-2-carboxaldehyde. All the invention compounds were evaluated for their ability to potentiate mGluR2. From the assay, it was determined that compound II exhibited EC50 value of < 0.0193 μM. The experimental process involved the reaction of 3-Chloro-4-nitrobenzonitrile(cas: 34662-29-8).Formula: C7H3ClN2O2
The Article related to benzimidazolyl compound preparation potentiator mglur2 treatment disease, Heterocyclic Compounds (More Than One Hetero Atom): Imidazoles and other aspects.Formula: C7H3ClN2O2
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts