1356385-98-2

Usage

Structure

Benzimidazole derivative with a trifluoromethyl group and a fluoropyridinyl substituent

Usage

Building block in the synthesis of pharmaceuticals and agrochemicals

Applications

Development of new drugs and crop protection products

Value

Valuable tool for chemical research and development due to its unique structure and properties

Upstream product

• 677728-92-6 2-fluoro-5-formylpyridine 
• 368-71-8 4-(trifluoromethyl)-1,2-phenylenediamine 

Downstream Products

• 1356384-93-4 C₂₈H₂₄F₃N₅O₄ 
• 1415571-94-6 3-[(1-{5-[5-(trifluoromethyl)-1H-benzimidazol-2-yl]pyridin-2-yl}piperidin-4-yl)oxy]benzoic acid 
• 1415574-02-5 cis-ethyl 4-((1-(5-(5-(trifluoromethyl)-1H-benzo[d]imidazol-2-yl)pyridin-2-yl)piperidin-4-yl)oxy)cyclohexanecarboxylate 
• 1415571-46-8 trans-4-((1-(5-(5-(trifluoromethyl)-1Hbenzo[d]imidazol-2-yl)pyridin-2-yl)piperidin-4-yl)oxy)cyclohexanecarboxylic acid 
• 1415574-03-6 trans-ethyl 4-((1-(5-(5-(trifluoromethyl)-1H-benzo[d]imidazol-2-yl)pyridin-2-yl)piperidin-4-yl)oxy)cyclohexanecarboxylate 
• 1415571-77-5 cis-1-methyl-4-[(1-{5-[6-(trifluoromethyl)-1H-benzimidazol-2-yl]pyridin-2-y}piperidin-4-yl)oxy]cyclohexanecarboxylic acid 
• 1415574-05-8 ethyl cis-1-methyl-4-[(1-{5-[6-(trifluoromethyl)-1H-benzimidazol-2-yl]pyridin-2-yl}piperidin-4-yl)oxy]cyclohexanecarboxylate 
• 1415571-93-5 methyl 3-[(1-{5[5-(trifluoromethyl)-1H-benzimidazol-2-yl]pyridin-2-yl}piperidin-4-yl)oxy]benzoate 

Relevant academic research and scientific papers

Microscale High-Throughput Experimentation as an Enabling Technology in Drug Discovery: Application in the Discovery of (Piperidinyl)pyridinyl-1H-benzimidazole Diacylglycerol Acyltransferase 1 Inhibitors

Miniaturization and parallel processing play an important role in the evolution of many technologies. We demonstrate the application of miniaturized high-throughput experimentation methods to resolve synthetic chemistry challenges on the frontlines of a lead optimization effort to develop diacylglycerol acyltransferase (DGAT1) inhibitors. Reactions were performed on ～1 mg scale using glass microvials providing a miniaturized high-throughput experimentation capability that was used to study a challenging SNAr reaction. The availability of robust synthetic chemistry conditions discovered in these miniaturized investigations enabled the development of structure-activity relationships that ultimately led to the discovery of soluble, selective, and potent inhibitors of DGAT1.

Discovery of a potent and selective DGAT1 inhibitor with a piperidinyl-oxy-cyclohexanecarboxylic acid moiety

We report the discovery of a novel series of DGAT1 inhibitors in the benzimidazole class with a piperdinyl-oxy-cyclohexanecarboxylic acid moiety. This novel series possesses significantly improved selectivity against the A2A receptor, no ACAT1 off-target activity at 10 μM, and higher aqueous solubility and free fraction in plasma as compared to the previously reported pyridyl-oxy-cyclohexanecarboxylic acid series. In particular, 5B was shown to possess an excellent selectivity profile by screening it against a panel of more than 100 biological targets. Compound 5B significantly reduces lipid excursion in LTT in mouse and rat, demonstrates DGAT1 mediated reduction of food intake and body weight in mice, is negative in a 3-strain Ames test, and appears to distribute preferentially in the liver and the intestine in mice. We believe this lead series possesses significant potential to identify optimized compounds for clinical development.

IMIDAZOLE DERIVATIVES

Described herein are compounds of formula (I), The compounds of formula I act as DGAT1 inhibitors and can be useful in preventing, treating or acting as a remedial agent for hyperlipidemia, diabetes mellitus and obesity.

SPIROCYCLIC COMPOUNDS

Described herein are compounds of formula (I) (Formula (I)). The compounds of formula (I) act as DGAT1 inhibitors and can be useful in preventing, treating or acting as a remedial agent for hyperlipidemia, diabetes mellitus and obesity.