697278-41-4

Upstream product

• 105-58-8 Diethyl carbonate 
• 98280-45-6 2-amino-4-chloro-N-hydroxybenzamidine 

Downstream Products

• 697278-53-8 1-[5-chloro-2-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-phenyl]-3-(3-trifluoromethyl-phenyl)-urea 
• 1034331-88-8 (E)-N-[5-chloro-2-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-phenyl]-3-naphthalen-2-yl-acrylamide 
• 1080451-02-0 N-[5-chloro-2-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-phenyl]-2-(3-methanesulfonyl-phenyl)-acetamide 
• 1080451-00-8 N-[5-chloro-2-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-phenyl]-2-[4-(piperidine-1-sulfonyl)-phenyl]-acetamide 
• 1083418-79-4 4-{5-[5-chloro-2-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-phenylcarbamoyl]-4-methyl-thiazol-2-yl}-piperidine-1-carboxylic acid tert-butyl ester 
• 1083418-77-2 2-(3-chloro-phenyl)-5-methyl-2H-[1,2,3]triazole-4-carboxylic acid [5-chloro-2-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-phenyl]-amide 
• 1083418-81-8 4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid [5-chloro-2-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-phenyl]-amide 
• 1083418-67-0 5-(4-chloro-phenyl)-2-methyl-furan-3-carboxylic acid [5-chloro-2-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-phenyl]-amide 
• 1083418-73-8 4-methyl-2-morpholin-4-yl-thiazole-5-carboxylic acid [5-chloro-2-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-phenyl]-amide 
• 1083418-71-6 1-(4-bromo-benzyl)-5-methyl-1H-[1,2,3]triazole-4-carboxylic acid [5-chloro-2-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-phenyl]-amide 
• 1083418-59-0 5-trifluoromethyl-2(4-trifluoromethyl-phenyl)-oxazole-4-carboxylic acid [5-chloro-2-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-phenyl]-amide 
• 1083418-69-2 2-(4-chloro-benzyl)-thiazole-4-carboxylic acid [5-chloro-2-(5-oxo-2,5-dihydro-[1,2,4]oxadiazol-3-yl)-phenyl]-amide 
• 1159704-74-1 N-[5-chloro-2-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-phenyl]-3-(3-chloro-phenyl)-propionamide 
• 1159711-30-4 N-[5-chloro-2-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-phenyl]-3,5-bis-trifluoromethyl-benzamide 

Relevant academic research and scientific papers

Bioisosteric modifications of 2-arylureidobenzoic acids: Selective noncompetitive antagonists for the homomeric kainate receptor subtype GluR5

2-Arylureidobenzoic acids (AUBAs) have recently been presented as the first series of selective noncompetitive GluR5 antagonists. In this paper we have modified the acidic moiety of the AUBAs by introducing different acidic and neutral groups, and similarly, we have replaced the urea linker of the AUBAs with other structurally related linkers. Replacing the acid with neutral substituents led to inactive compounds in all instances, showing that an acidic moiety is necessary for activity. Replacing the carboxylic moiety in 2a with a sulfonic acid (5c) or a tetrazole ring (5d) improved the potency at GluR5 receptors (compounds 5c and 5d showed IC50 values of 1.5 and 2.0 μM, respectively, compared to compound 2a with IC50 = 4.8 μM). Compound 5c did not show improved in vivo activity in the ATPA rigidity test compared to 2a, whereas compound 5d was 4 times more potent than 2a. All compounds wherein the urea linker had been replaced showed lower or no activity. The results described extend the knowledge of structure-activity relationships for the AUBAs, and compound 5d may prove to be a good candidate for studying GluR5 receptors in vitro and in vivo.

NOVEL ARYL UREIDO BENZOIC ACID DERIVATIVES AND THEIR USE

This invention relates to novel aryl ureido benzoic acid derivatives useful as selective and non-competitive antagonists of the ionotropic GluR5 receptor. Due to their biological activity, the aryl ureido derivatives of the invention are considered useful for treating diseases that are responsive to modulation of an aspartate or a glutamate receptor. Moreover the invention provides chemical compounds for use according to the invention, as well as pharmaceutical compositions comprising the chemical compounds, and methods of treating diseases or disorders or conditions responsive to modulation of an aspartate or a glutamate receptor.