636581-62-9

Upstream product

• 57113-91-4 methyl 3-nitroanthranilate 
• 52727-57-8 5-bromo-2-aminobenzoic acid methyl ester 
• 636581-60-7 5-bromo-3-nitro-2-(2,2,2-trifluoroacetylamino)benzoic acid methyl ester 
• 636581-61-8 2-amino-5-bromo-3-nitrobenzoic acid methyl ester 
• 1692-25-7 3-pyridylboronic acid 

Downstream Products

• 636581-63-0 methyl-2,3-diamino-5-(3'-pyridyl) benzoate 

Relevant academic research and scientific papers

Novel dual-targeting benzimidazole urea inhibitors of DNA gyrase and topoisomerase IV possessing potent antibacterial activity: Intelligent design and evolution through the judicious use of structure-guided design and stucture-activity relationships

The discovery of new antibacterial agents with novel mechanisms of action is necessary to overcome the problem of bacterial resistance that affects all currently used classes of antibiotics. Bacterial DNA gyrase and topoisomerase IV are well-characterized clinically validated targets of the fluoroquinolone antibiotics which exert their antibacterial activity through inhibition of the catalytic subunits. Inhibition of these targets through interaction with their ATP sites has been less clinically successful. The discovery and characterization of a new class of low molecular weight, synthetic inhibitors of gyrase and topoisomerase IV that bind to the ATP sites are presented. The benzimidazole ureas are dual targeting inhibitors of both enzymes and possess potent antibacterial activity against a wide spectrum of relevant pathogens responsible for hospital- and community-acquired infections. The discovery and optimization of this novel class of antibacterials by the use of structure-guided design, modeling, and structure-activity relationships are described. Data are presented for enzyme inhibition, antibacterial activity, and in vivo efficacy by oral and intravenous administration in two rodent infection models.

ANTIBACTERIAL COMPOSITIONS

Compounds of formula (I) have antibacterial activity: wherein: m is 0 or 1 ; Q is hydrogen or cyclopropyl; AIk is an optionally substituted, divalent C1-C6 alkylene, alkenylene or alkynylene radical which may contain an ether (-O-), thioether (-S-) or amino (-NR)- link, wherein R is hydrogen, -CN or C1-C3 alkyl; X is -C(=O)NR6-, -S(O)NR6-, -C(=O)O- or -S(=O)O- wherein R6 is hydrogen, optionally substituted C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, -Cyc, or -( C1-C3 alkyl)-Cyc wherein Cyc is optionally substituted monocyclic carbocyclic or heterocyclic having 3-7 ring atoms; Z is N or CH, or CF; R2 and R3 are as defined in the description.

2-UREIDO-6-HETEROARYL-3H-BENZOIMIDAZOLE-4-CARBOXYLIC ACID DERIVATIVES AND RELATED COMPOUNDS AS GYRASE AND/OR TOPOISOMERASE IV INHIBITORS FOR THE TREATMENT OF BACTERIAL INFECTIONS

The present invention relates to compounds of formula I, wherein X, Q, W, R1, R2 and R3 are as defined in the claims, which inhibit bacterial gyrase and/or Topo IV and pharmaceutically acceptable compositions comprising said compounds. These compounds, and compositions thereof, are useful in treating bacterial infection. Accordingly, the present invention also relates to methods for treating bacterial infections in, mammals. The present invention also relates to a method for preparing these compounds.