691905-10-9

Basic information

• Product Name: ethyl 3-(2,6-difluoro-4-methoxyphenyl)propanoate
• Synonyms: ethyl 3-(2,6-difluoro-4-methoxyphenyl)propanoate
• CAS NO: 691905-10-9
• Molecular Formula: C₁₂H₁₄F₂O₃
• Molecular Weight: 244.2345664
• Mol File: 691905-10-9.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: ethyl 3-(2,6-difluoro-4-methoxyphenyl)propanoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 3-(2,6-difluoro-4-methoxyphenyl)propanoate(691905-10-9)
• EPA Substance Registry System: ethyl 3-(2,6-difluoro-4-methoxyphenyl)propanoate(691905-10-9)

Safety Data

• Hazardous Substances Data: 691905-10-9(Hazardous Substances Data)

Upstream product

• 256417-10-4 2,6-difluoro-4-methoxybenzaldehyde 
• 123843-65-2 2,6-difluoro-4-methoxybenzoic acid 
• 140-88-5 ethyl acrylate 
• 858114-78-0 ethyl (2E)-3-(2,6-difluoro-4-methoxyphenyl)acrylate 

Downstream Products

• 691902-74-6 3-{4-[(2',6'-dimethylbiphenyl-3-yl)methoxy]-2,6-difluorophenyl}propanoic acid 
• 691902-73-5 ethyl 3-(2,6-difluoro-4-((2',6'-dimethylbiphenyl-3-yl)methoxy)phenyl)propanoate 
• 691905-11-0 ethyl 3-(2,6-difluoro-4-hydroxyphenyl)-propanoate 

Relevant articles and documents

Design, synthesis, and biological activity of potent and orally available g protein-coupled receptor 40 agonists

G protein-coupled receptor 40 (GPR40) is being recently considered to be a new potential drug target for the treatment of type 2 diabetes because of its role in the enhancement of free fatty acid-regulated glucose-stimulated insulin secretion in pancreatic β-cells. We initially identified benzyloxyphenylpropanoic acid (1b) (EC50 = 510 nM), which was designed based on the structure of free fatty acids, as a promising lead compound with GPR40 agonist activity. Chemical modification of compound 1b led to the discovery of 3-{4-[(2′,6′-dimethylbiphenyl-3-yl)methoxy]-2- fluorophenyl}propanoic acid (4p) as a potent GPR40 agonist (EC50 = 5.7 nM). Compound 4p exhibited acceptable pharmacokinetic profiles and significant glucose-lowering effects during an oral glucose tolerance test in diabetic rats. Moreover, no hypoglycemic event was observed even after administration of a high dose of compound 4p to normal fasted rats. These pharmacological results suggest that GPR40 agonists might be novel glucose-dependent insulin secretagogues with little or no risk of hypoglycemia.

PHENYLPROPANOIC ACID DERIVATIVES

The present invention provides a novel compound having a GPR40 receptor function modulating action, which is useful as an insulin secretagogue, a drug for the prophylaxis or treatment of diabetes and the like. A compound represented by the formula (I) wherein each symbol is as defined in the specification, a salt thereof and a prodrug thereof have unexpectedly superior GPR40 receptor agonist activity and also show superior properties as a pharmaceutical product, such as stability and the like. Thus, they can be safe and useful drugs for the prophylaxis or treatment of GPR40 receptor related conditions or diseases in mammals.

RECEPTOR FUNCTION CONTROLLING AGENT

The GPR40 receptor function regulator of the present invention, which comprises a compound having an aromatic ring and a group capable of releasing cation is useful as an insulin secretagogue or an agent for the prophylaxis or treatment of diabetes and the like.