On March 10, 2022, Lerner, Christian; Li, Mingming; Liu, Yongqiang; Schmitt, Sebastien; Wang, Jianhua; Wang, Min; Wang, Yongguang; Yang, Song; Zhou, Chengang published a patent.COA of Formula: C4H6N2O The title of the patent was Preparation of imidazole-pyrazole derivatives with anti-bacterial properties. And the patent contained the following:
The invention provides imidazole pyrazole derivatives having formula I, and pharmaceutically acceptable salts thereof. Further provided are pharmaceutical compositions including the compounds, processes of manufacturing the compounds and methods of using the compounds as medicaments, in particular methods of using the compounds as antibiotics for the treatment or prevention of bacterial infections and resulting diseases. Compounds of formula I wherein R1R2 may be taken together to form substituted nitrogen-containing heterocycle; R1 is C1-6 alkyl, amino-C1-6 alkyl, amino-C1-6 alkoxy-C1-6 alkyl, etc.; R2 is H and C1-6 alkyl; R3 is H, halo, C1-6 alkyl and C1-6 alkoxy; R4 and R6 are independently H, C1-6 alkyl, C1-6 alkoxy, CN, etc.; R5a, R5b and R5c are H, halo, OH, C1-6 alkyl, C1-6 alkoxy, etc.; A is 5- to 14- membered heteroaryl; and pharmaceutically acceptable salts thereof, are claimed. Example compound II•HCO2H was prepared by arylation of tert-Bu 4-(4-(2-chloro-4-(1-methyl-5-(3-(trifluoromethyl)-1H-pyrazol-4-yl)-imidazole-2-carboxamido)benzoyl)piperazine-1-carbonyl)piperidine-1-carboxylate with 2-chloropyrimidine; the resulting tert-Bu 4-(4-(2-chloro-4-(1-methyl-5-(1-(pyrimidin-2-yl)-3-(trifluoromethyl)-pyrazol-4-yl)-imidazole-2-carboxamido)benzoyl)piperazine-1- carbonyl)piperidine-1-carboxylate underwent hydrolysis to give compound II•HCO2H. The invention compounds were evaluated for their antibacterial activity. From the assay, it was determined that compound II exhibited IC90 value of 0.69μM. The experimental process involved the reaction of 5-Methoxy-1H-pyrazole(cas: 215610-30-3).COA of Formula: C4H6N2O
The Article related to imidazole pyrazole preparation antibacterial, Heterocyclic Compounds (More Than One Hetero Atom): Imidazoles and other aspects.COA of Formula: C4H6N2O
Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics