1000413-72-8

Basic information

• Product Name: TAK875
• Synonyms: TAK875;3-Benzofuranacetic acid, 6-[[2',6'-diMethyl-4'-[3-(Methylsulfonyl)propoxy][1,1'-biphenyl]-3-yl]Methoxy]-2,3-dihydro-, (3S)-;(3S)-6-[[2',6'-Dimethyl-4'-[3-(methylsulfonyl)propoxy][1,1'-biphenyl]-3-yl]methoxy]-2,3-dihydro-3-benzofuranacetic acid;TAK-875,TAK875;[(3S)-6-({2',6'-Dimethyl-4'-[3-(methylsulfonyl)propoxy]-3-biphenylyl}methoxy)-2,3-dihydro-1-benzofuran-3-yl]acetic acid;(S)-2-(6-((2',6'-Dimethyl-4'-(3-(methylsulfonyl)propoxy)-[1,1'-biphenyl]-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetic acid;TAK-875, >=98%;Fasiglifam
• CAS NO: 1000413-72-8
• Molecular Formula: C29H32O7S
• Molecular Weight: 524.62518
• EINECS: -0
• Product Categories: Inhibitors
• Mol File: 1000413-72-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 739.1±60.0 °C(Predicted)
• Appearance: /
• Density: 1.252
• Storage Temp.: Refrigerator
• Solubility: Acetonitrile (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 4.36±0.10(Predicted)
• CAS DataBase Reference: TAK875(CAS DataBase Reference)
• NIST Chemistry Reference: TAK875(1000413-72-8)
• EPA Substance Registry System: TAK875(1000413-72-8)

Safety Data

• Hazardous Substances Data: 1000413-72-8(Hazardous Substances Data)

Usage

Description

The free fatty acid receptor 1 (FFAR1; GPR40) is highly expressed in pancreatic β-cells and activated by medium and long-chain fatty acids. There is evidence of a link between FFAR1 (GPR40) and the ability of fatty acids to amplify glucose-stimulated insulin secretion, making this signaling pathway a potential target for regulating diabetes, obesity, and other metabolic disorders. TAK-875 is a selective FFAR1 (GPR40) agonist (EC50 = 26 nM) that does not exhibit activity on the related FFARs FFAR2 (GPR43) or FFAR3 (GPR41).

Uses

Different sources of media describe the Uses of 1000413-72-8 differently. You can refer to the following data:
1. TAK-876 is a selective G protein-coupled receptor 40 (GPR40) agonist. TAK-876 is a novel oral medication that has been developed to improve the secretion of insulin in a glucose-dependent manner, whic h has the potential to improve the control of blood sugar levels without the risk of hypoglycemia.
2. TAK-876 is a selective G protein-coupled receptor 40 (GPR40) agonist (1,2). TAK-876 is a novel oral medication that has been developed to improve the secretion of insulin in a glucose-dependent manner, which has the potential to improve the control of blood sugar levels with a low risk of hypoglycemia.

in vitro

tak-875 exhibited potent agonist activity and high binding affinity to the human receptor. in addition, tak-875 showed excellent agonist potency selectivity for gpr40 receptor over other members of the ffa receptor family (for which ec50>10 μm) [1].

in vivo

tak-875 showed potent plasma glucose-lowering action and insulinotropic action during an oral glucose tolerance test in female wistar fatty rats with impaired glucose tolerance [2].

references

[1] negoro n, sasaki s, mikami s, ito m, suzuki m, tsujihata y, ito r, harada a, takeuchi k, suzuki n, miyazaki j, santou t, odani t, kanzaki n, funami m, tanaka t1, kogame a, matsunaga s, yasuma t, momose y. discovery of tak-875: a potent, selective, and orally bioavailable gpr40 agonist. acs med chem lett. 2010 jun 18;1(6):290-4. [2] leifke e, naik h, wu j, viswanathan p, demanno d, kipnes m, vakilynejad m. a multiple-ascending-dose study to evaluate safety, pharmacokinetics, and pharmacodynamics of a novel gpr40 agonist, tak-875, in subjects with type 2 diabetes. clin pharmacol ther. 2012 jul;92(1):29-39.

Upstream product

• 25392-41-0 4-chloromethyl-7-hydroxycoumarin 
• 108-46-3 recorcinol 
• 87199-15-3 [3-(hydroxymethyl)phenyl]boronic acid 
• 726174-52-3 (6-hydroxy-benzofuran-3-yl)-acetic acid methyl ester 
• 69716-04-7 2-(6-hydroxy-1-benzofuran-3-yl)acetic acid 
• 1000413-84-2 2',6'-dimethyl-4'-(3-(methylsulfonyl)propoxy)-[1,1'-biphenyl]-3-carbaldehyde 
• 1000413-85-3 (2’,6’-dimethyl-4’-(3-(methylsulfonyl)propoxy)-[1,1‘-biphenyl]-3-yl)methanol 
• 1000414-38-9 methyl ((3S)-6-hydroxy-2,3-dihydro-1-benzofuran-3-yl)acetate 
• 1394138-49-8 3'-(chloromethyl)-2,6-dimethyl-4-(3-(methylsulfonyl)propoxy)-1,1'-biphenyl 
• 1394138-60-3 methanesulfonic acid 4’-(3-methanesulfonylpropoxy)-2’,6’-dimethylbiphenyl-3-ylmethyl ester 
• 1258399-02-8 methyl [(3S)-6-{[(trifluoromethyl)sulfonyl]oxy}-2,3-dihydro-1-benzofuran-3-yl]acetate 
• 87199-16-4 3-Formylphenylboronic acid 
• 1394138-45-4 (6-hydroxy-1-benzofuran-3-yl)acetic acid (1R)-1-phenylethylamine salt 
• 1394138-46-5 [(3S)-6-hydroxy-2,3-dihydro-1-benzofuran-3-yl]acetic acid (1R)-1-phenylethylamine salt 

Relevant articles and documents

A 2 - (6-hydroxy -2,3-dihydrobenzo-furan-3-yl) acetonitrile TAK-875 compound preparation compound and method

The present invention particularly relates to a chiral compound 2-(6-hydroxy-2,3-dihydro benzofuran-3-yl)acetonitrile and a preparation method thereof, and a method for preparing a TAK-875 drug by adopting the compound as an intermediate. Compared with the TAK-875 synthesis method reported in the literature, the method for preparing the TAK-875 by adopting the chiral compound 2-(6-hydroxy-2,3-dihydro benzofuran-3-yl)acetonitrile in the present invention has the following advantages that: the single maximum impurity, the content, the yield, the optical purity and other characteristics of the obtained TAK-875 in the present invention are superior to the TAK-875 obtained through the method in the literature, and the method is suitable for industrial mass production.

FUSED CYCLIC COMPOUNDS

The present invention provides a compound represented by the formula (I): wherein each symbol is as defined in the description, or a salt thereof. The compound or a salt thereof or a prodrug thereof has a GPR40 receptor function modulating action and is useful as an insulin secretagogue or an agent for the prophylaxis or treatment of diabetes and the like.