1628264-07-2

Usage

Uses

Used in Organic Synthesis:
(6-bromo-2-ethyl-8-methyl-imidazo[1,2-a]pyridin-3-yl)-methyl-amine is used as a synthetic building block for the creation of more complex organic molecules. Its unique combination of functional groups and structural elements makes it a valuable precursor in the synthesis of various compounds, potentially leading to novel materials and pharmaceuticals.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (6-bromo-2-ethyl-8-methyl-imidazo[1,2-a]pyridin-3-yl)-methyl-amine is used as a starting material or intermediate for the development of new drugs. Its structural features may endow it with specific biological activities, making it a promising candidate for further research and potential therapeutic applications.
Further Research:
Given the complex nature of (6-bromo-2-ethyl-8-methyl-imidazo[1,2-a]pyridin-3-yl)-methyl-amine, additional studies are necessary to fully comprehend its properties, reactivity, and potential applications. This may include exploring its interactions with other molecules, assessing its stability under various conditions, and investigating any possible toxicological or environmental impacts.

Upstream product

• 3430-21-5 5-bromo-3-methyl-pyridin-2-ylamine 

Downstream Products

• 1628260-79-6 2-[[2-ethyl-6-[4-[2-(3-hydroxyazetidin-1-yl)-2-oxoethyl]piperazin-1-yl]-8-methylimidazo[1,2-α]pyridin-3-yl]-(methyl)amino]-4-(4-fluorophenyl)thiazole-5-carbonitrile 

Relevant academic research and scientific papers

Catalyst-Free Cyclization- And Curtius Rearrangement-Induced Functional Group Transformation: An Improved Synthetic Strategy of First-in-Class ATX Inhibitor Ziritaxestat (GLPG-1690)

A practical and highly efficient protocol for the production of Autotaxin (ATX) inhibitor Ziritaxestat (1) was described. The procedure began with a catalyst-free bicomponent cyclization for the construction of the imidazo[1,2-a]pyridine skeleton 16. Subsequently, a typical Curtius rearrangement of carboxylic acid 17 followed by nucleophilic attacking of 3,5-dichlorobenzyl alcohol 18f led to the carbamate analogue 19f. N-methylated 20 was readily deprotected through HBr/HOAc treatment, which further conveniently took part in an alternative K2CO3-induced N-alkylation reaction with 9 to give 10. 10 coupled directly with piperazine to furnish 13, which ideally circumvent the removal of the Boc group. As a result, the hypertoxic KCN and the hypertoxic and costly isonitrile 3 involved in the tricomponent cyclization were carefully avoided. Ultimately, a novel, scalable, and cost-effective route was favorably developed to afford Ziritaxestat in a 20.4% overall yield.

Synthetic method of ATX inhibitor Ziritaxestat

The invention belongs to the field of medicinal chemistry, relates to a synthesis method of ATX inhibitor Ziritaxestat, in particular relates to a preparation method of the ATX inhibitor Ziritaxestatbased on a pyridino imidazole parent nucleus, and further relates to a synthesis method of an intermediate for preparing the inhibitor. The method relates to eight-step reaction, and comprises the following steps: firstly, carrying out cyclization reaction, esterolysis, Curtius rearrangement, methylation, benzyl protection removal, N-aromatization, Buchwald-Hartwig coupling and N-alkylation to obtain the final product Ziritaxestat. The synthesis method is a brand-new synthesis method of the Ziritaxestat, raw materials required by the whole reaction are cheap and easy to obtain, highly toxic reagents such as sodium cyanide and isonitrile are avoided, the reaction conditions are mild, the operation is simple, convenient and feasible, and the synthesis method is suitable for large-scale production.

Discovery of 2-[[2-Ethyl-6-[4-[2-(3-hydroxyazetidin-1-yl)-2-oxoethyl]piperazin-1-yl]-8-methylimidazo[1,2-a]pyridin-3-yl]methylamino]-4-(4-fluorophenyl)thiazole-5-carbonitrile (GLPG1690), a First-in-Class Autotaxin Inhibitor Undergoing Clinical Evaluation for the Treatment of Idiopathic Pulmonary Fibrosis

Autotaxin is a circulating enzyme with a major role in the production of lysophosphatic acid (LPA) species in blood. A role for the autotaxin/LPA axis has been suggested in many disease areas including pulmonary fibrosis. Structural modifications of the known autotaxin inhibitor lead compound 1, to attenuate hERG inhibition, remove CYP3A4 time-dependent inhibition, and improve pharmacokinetic properties, led to the identification of clinical candidate GLPG1690 (11). Compound 11 was able to cause a sustained reduction of LPA levels in plasma in vivo and was shown to be efficacious in a bleomycin-induced pulmonary fibrosis model in mice and in reducing extracellular matrix deposition in the lung while also reducing LPA 18:2 content in bronchoalveolar lavage fluid. Compound 11 is currently being evaluated in an exploratory phase 2a study in idiopathic pulmonary fibrosis patients.

COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS THEREOF FOR THE TREATMENT OF INFLAMMATORY DISORDERS

The present invention discloses compounds according to Formula I: Wherein R1a, R1b, R2, R4, R5, R6a, R6b, R7, R8, W, X, Cy, and the subscript a are as defined herein. The present invention relates to compounds inhibiting autotaxin (NPP2 or ENPP2), methods for their production, pharmaceutical compositions comprising the same, and methods of treatment using the same, for the prophylaxis and/or treatment of diseases involving fibrotic diseases, proliferative diseases, inflammatory diseases, autoimmune diseases, respiratory diseases, cardiovascular diseases, neurodegenerative diseases, dermatological disorders, and/or abnormal angiogenesis associated diseasesby administering the compound of the invention.