1151801-90-9

Usage

Organic compound

It is an organic compound because it is primarily composed of carbon atoms along with hydrogen, and possibly other elements such as oxygen, nitrogen, and fluorine.

Pyridine ring

The compound contains a pyridine ring, which is a six-membered aromatic heterocyclic ring with one nitrogen atom replacing one carbon atom in a benzene ring.

Substituted with two fluorine atoms

The pyridine ring in 2,3-difluoro-5-(1-methyl-1H-pyrazol-4-yl)pyridine has two fluorine atoms attached to it, which can influence its chemical reactivity, polarity, and other properties.

1-methyl-1H-pyrazol-4-yl group

This functional group is attached to the pyridine ring and consists of a pyrazole ring (a five-membered ring with two nitrogen atoms) with a methyl group (a CH3 group) attached to the 1-position and a pyridine ring at the 4-position.

Pharmaceutical research and drug development

2,3-difluoro-5-(1-methyl-1H-pyrazol-4-yl)pyridine is used as a potential medicinal agent due to its diverse pharmacological properties, making it a valuable compound for creating new drugs and therapies.

Synthesis of various organic compounds

The compound can be used as a starting material or intermediate in the synthesis of other organic compounds, allowing for the creation of a wide range of molecules with different properties and applications.

Building block in the production of new materials

2,3-difluoro-5-(1-methyl-1H-pyrazol-4-yl)pyridine can be used as a building block for the development of new materials with unique properties, making it an important chemical for both scientific and industrial applications.

Upstream product

• 89402-44-8 5-bromo-2,3-difluoropyridine 
• 761446-44-0 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole 
• 89402-43-7 5-chloro-2,3-difluoropyridine 
• 847818-55-7 (1-methyl-1H-pyrazol-4-yl)boronic acid 

Downstream Products

• 1173699-31-4 AMG 337 
• 1173699-31-4 6-(1-(8-Fluoro-6-(1-methyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)ethyl)-3-(2-methoxyethoxy)-1,6-naphthyridin-5(6H)-one 

Relevant academic research and scientific papers

Synthesis and biological evaluation of new [1,2,4]triazolo[4,3-a]pyridine derivatives as potential c-Met inhibitors

A series of [1,2,4]triazolo[4,3-a]pyrazine derivatives (4a–4i) were designed, synthesized and evaluated for their c-Met kinase inhibition and antitumor activity against SNU5 gastric cell line in vitro. Among these compounds, 4d was found to show the highest activity against c-Met and high selectivity against the tumor cells which are believed to be dependent on the c-Met oncogene amplification, because 4d selectively inhibited c-Met while had no effect on other 59 kinases. In vivo efficacy study on human gastric (MKN-45) and human non-small cell lung (NCI-H1993) tumor xenograft in nude mouse demonstrated that 4d·CH3SO3H had a better inhibiting activity than SGX-523 in a dose-dependent manner. When tested in mice, compound 4d·CH3SO3H was found to have biological half-lives and plasma exposure values higher than those of JNJ-38877605, and its long-term toxicity and acute toxicity turned out to be acceptable, all of which indicates that 4d·CH3SO3H is a desirable drug candidate.

Discovery of (R)-6-(1-(8-Fluoro-6-(1-methyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)ethyl)-3-(2-methoxyethoxy)-1,6-naphthyridin-5(6H)-one (AMG 337), a Potent and Selective Inhibitor of MET with High Unbound Target Coverage and Robust in Vivo Antitumor Activity

Deregulation of the receptor tyrosine kinase mesenchymal epithelial transition factor (MET) has been implicated in several human cancers and is an attractive target for small molecule drug discovery. Herein, we report the discovery of compound 23 (AMG 337), which demonstrates nanomolar inhibition of MET kinase activity, desirable preclinical pharmacokinetics, significant inhibition of MET phosphorylation in mice, and robust tumor growth inhibition in a MET-dependent mouse efficacy model.

Discovery of potent and selective 8-fluorotriazolopyridine c-met inhibitors

The overexpression of c-Met and/or hepatocyte growth factor (HGF), the amplification of the MET gene, and mutations in the c-Met kinase domain can activate signaling pathways that contribute to cancer progression by enabling tumor cell proliferation, survival, invasion, and metastasis. Herein, we report the discovery of 8-fluorotriazolopyridines as inhibitors of c-Met activity. Optimization of the 8-fluorotriazolopyridine scaffold through the combination of structure-based drug design, SAR studies, and metabolite identification provided potent (cellular IC50 a mouse liver pharmacodynamic model.

METHOD FOR THE PREPARATION OF (1,2,4)-TRIAZOLO(4,3-A)PYRIDINES

Disclosed herein are methods for preparing [1,2,4]triazolo[4,3-a]pyridines, particularly (R)-6-(1-(8-fluoro-6-(l-methyl4H-pyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)ethyl)-3-(2- methoxyethoxy)- 1,6-naphthyridin-5(6H)-one, and precursors thereof.

6 - SUBSTITUTED 3 - (QUINOLIN- 6 - YLTHIO) - [1,2,4] TRIAZOLO [4, 3 -A] PYRADINES AS TYROSINE KINASE

The invention relates to compounds of formula (I) and salts thereof: Formula (I) wherein the substituents are as defined in the specification; a compound of formula (I) for use in the treatment of the human or animal body, in particular with regard to c-Met tyrosine kinase mediated diseases or conditions; the use of a compound of formula (I) for manufacturing a medicament for the treatment of such diseases; pharmaceutical compositions comprising a compound of the formula (I), optionally in the presence of a combination partner, and processes for the preparation of a compound of formula (I).

TRIAZOLOPYRIDINE COMPOUNDS

The invention relates to compounds of formula (I) and salts thereof: wherein the substituents are as defined in the specification; a compound of formula (I) for use in the treatment of the human or animal body, in particular with regard to c-Met tyrosine kinase mediated diseases or conditions; the use of a compound o f formula (I) for manufacturing a medicament for the treatment of such diseases; pharmaceutical compositions comprising a compound of the formula (I), optionally in the presence of a combination partner, and processes for the preparation of a compound of formula (I)