648927-52-0

Basic information

• Product Name: Benzamide, N-[[(5-amino-2-methoxyphenyl)amino]carbonyl]-2-chloro-4,5-difluoro-
• CAS NO: 648927-52-0
• Molecular Formula: C15H12ClF2N3O3
• Molecular Weight: 355.728
• Mol File: 648927-52-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Benzamide, N-[[(5-amino-2-methoxyphenyl)amino]carbonyl]-2-chloro-4,5-difluoro-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzamide, N-[[(5-amino-2-methoxyphenyl)amino]carbonyl]-2-chloro-4,5-difluoro-(648927-52-0)
• EPA Substance Registry System: Benzamide, N-[[(5-amino-2-methoxyphenyl)amino]carbonyl]-2-chloro-4,5-difluoro-(648927-52-0)

Safety Data

• Hazardous Substances Data: 648927-52-0(Hazardous Substances Data)

Upstream product

• 99-59-2 3-amino-4-methoxynitrobenzene 
• 634616-77-6 2-chloro-4,5-difluorobenzoyl isocyanate 
• 296274-32-3 2-chloro-4,5-difluorobenzamide 
• 648927-51-9 1-(2-chloro-4,5-difluorophenyl)-3-(2-methoxy-5-nitrobenzoyl)urea 

Relevant articles and documents

Acyl ureas as human liver glycogen phosphorylase inhibitors for the treatment of type 2 diabetes

Using a focused screening approach, acyl ureas have been discovered as a new class of inhibitors of human liver glycogen phosphorylase (hiGPa). The X-ray structure of screening hit 1 (IC50 = 2 μM) in a complex with rabbit muscle glycogen phosphorylase b reveals that 1 binds at the AMP site, the main allosteric effector site of the dimeric enzyme. A first cycle of chemical optimization supported by X-ray structural data yielded derivative 21, which inhibited hlGPa with an IC50 of 23 ± 1 nM, but showed only moderate cellular activity in isolated rat hepatocytes (IC50 = 6.2 μM). Further optimization was guided by (i) a 3D pharmacophore model that was derived from a training set of 24 compounds and revealed the key chemical features for the biological activity and (ii) the 1.9 A? crystal structure of 21 in complex with hlGPa. A second set of compounds was synthesized and led to 42 with improved cellular activity (hlGPa IC50 = 53 ± 1 nM; hepatocyte IC50 = 380 nM). Administration of 42 to anaesthetized Wistar rats caused a significant reduction of the glucagon-induced hyperglycemic peak. These findings are consistent with the inhibition of hepatic glycogenolysis and support the use of acyl ureas for the treatment of type 2 diabetes.

CARBONYL-AMINO SUBSTITUTED ACYL PHENYL UREA DERIVATIVES, METHOD FOR THE PRODUCTION AND USE THEREOF

The invention relates to compounds of formula (I) wherein the radicals have the cited meaning, in addition to the physiologically compatible salts thereof. The compounds, for example, can be used as medicaments for preventing and treating type 2 diabetes.