805250-19-5

Usage

Uses

Used in Pharmaceutical Industry:
[1,1-Biphenyl]-3-methanol,2,4-dimethyl-(9CI) is used as an intermediate in the production of various pharmaceuticals for its ability to contribute to the synthesis of diverse medicinal compounds. Its structural properties allow for the creation of a wide range of drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical industry, [1,1-Biphenyl]-3-methanol,2,4-dimethyl-(9CI) is utilized as an intermediate in the synthesis of various agrochemicals, such as pesticides and herbicides. Its role in the development of these compounds aids in enhancing agricultural productivity and crop protection.
Used in Organic Compounds Synthesis:
[1,1-Biphenyl]-3-methanol,2,4-dimethyl-(9CI) is used as a key intermediate in the synthesis of other organic compounds, showcasing its versatility in chemical reactions and its potential for creating a variety of products with different applications.
Used in Novel Materials Synthesis:
[1,1-Biphenyl]-3-methanol,2,4-dimethyl-(9CI) has been studied for its potential use in the synthesis of novel materials, indicating its possible role in the development of new technologies and innovations in various industries.
Used as a Chiral Auxiliary in Asymmetric Synthesis:
[1,1-Biphenyl]-3-methanol,2,4-dimethyl-(9CI) is used as a chiral auxiliary in asymmetric synthesis, which is crucial for the production of enantiomerically pure compounds. This application is particularly important in the pharmaceutical industry, where the desired biological activity often resides in a single enantiomer.
Used in Medicinal Chemistry and Drug Discovery:
[1,1-Biphenyl]-3-methanol,2,4-dimethyl-(9CI)'s various biological activities have made it a subject of interest in medicinal chemistry and drug discovery. Researchers are exploring its potential for developing new therapeutic agents and understanding its interactions with biological targets.

Upstream product

• 24398-88-7 ethyl 3-bromobenzoate 
• 55499-44-0 2,4-dimethylbenzeneboronic acid 
• 805250-18-4 ethyl 2',4'-dimethylbiphenyl-3-carboxylate 

Downstream Products

• 805248-74-2 methyl 2-[6-((2',4'-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydro-1-benzofuran-3-yl]acetate 
• 805248-75-3 2-[6-[(2',4'-dimethylbiphenyl-3-yl)methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid 

Relevant academic research and scientific papers

Identification of fused-ring alkanoic acids with improved pharmacokinetic profiles that Act as G protein-coupled receptor 40/free fatty acid receptor 1 agonists

The G protein-coupled receptor 40 (GPR40)/free fatty acid receptor 1 (FFA1) has emerged as an attractive target for a novel insulin secretagogue with glucose dependency. We previously identified phenylpropanoic acid derivative 1 (3-{4-[(2′,6′-dimethylbiphenyl-3-yl)methoxy]-2-fluorophenyl} propanoic acid) as a potent and orally available GPR40/FFA1 agonist; however, 1 exhibited high clearance and low oral bioavailability, which was likely due to its susceptibility to β-oxidation at the phenylpropanoic acid moiety. To identify long-acting compounds, we attempted to block the metabolically labile sites at the phenylpropanoic acid moiety by introducing a fused-ring structure. Various fused-ring alkanoic acids with potent GPR40/FFA1 activities and good PK profiles were produced. Further optimizations of the lipophilic portion and the acidic moiety led to the discovery of dihydrobenzofuran derivative 53 ((6-{[4′-(2-ethoxyethoxy)-2′,6′-dimethylbiphenyl-3-yl]methoxy} -2,3-dihydro-1-benzofuran-3-yl)acetic acid), which acted as a GPR40/FFA1 agonist with in vivo efficacy during an oral glucose tolerance test (OGTT) in rats with impaired glucose tolerance.

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.

3-(4-BENZYLOXYPHENYL)PROPANOIC ACID DERIVATIVES

The present invention provides a novel compound represented by the formula (I) wherein each symbol is as defined in the specification, a salt thereof and a prodrug thereof having a superior GPR40 receptor function modulating action, which can be used as an insulin secretagogue, an agent for the prophylaxis or treatment of diabetes and the like. They unexpectedly show 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 pharmaceutical agents for the prophylaxis or treatment of GPR40 receptor related diseases in mammals.