1628260-79-6

Basic information

• Product Name: GLPG-1690
• Synonyms: GLPG-1690;2-((2-ethyl-6-(4-(2-(3-hydroxyazetidin-1-yl)-2-oxoethyl)piperazin-1-yl)-8-methylimidazo[1,2-a]pyridin-3-yl)(methyl)amino)-4-(4-fluorophenyl)thiazole-5-carbonitrile;5-Thiazolecarbonitrile, 2-[[2-ethyl-6-[4-[2-(3-hydroxy-1-azetidinyl)-2-oxoethyl]-1-piperazinyl]-8-methylimidazo[1,2-a]pyridin-3-yl]methylamino]-4-(4-fluorophenyl)-;GLPG11690
• CAS NO: 1628260-79-6
• Molecular Formula: C30H33FN8O2S
• Molecular Weight: 588.6988232
• EINECS: -0
• Product Categories: APIS;API
• Mol File: 1628260-79-6.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Density: 1.42±0.1 g/cm3(Predicted)
• PKA: 13.72±0.20(Predicted)
• CAS DataBase Reference: GLPG-1690(CAS DataBase Reference)
• NIST Chemistry Reference: GLPG-1690(1628260-79-6)
• EPA Substance Registry System: GLPG-1690(1628260-79-6)

Safety Data

• Hazardous Substances Data: 1628260-79-6(Hazardous Substances Data)

Usage

Description

GLPG-1690 is a selective autotaxin inhibitor developed by Galapagos, designed to target and inhibit the enzyme autotaxin, which plays a significant role in the pathogenesis of idiopathic pulmonary fibrosis (IPF) and other fibrotic diseases. It has shown promising results in terms of safety, tolerability, and target engagement in a Phase 1 study involving healthy human volunteers.

Uses

Used in Pharmaceutical Industry:
GLPG-1690 is used as a therapeutic agent for the treatment of idiopathic pulmonary fibrosis (IPF) due to its selective inhibition of autotaxin, an enzyme involved in the disease's progression. By inhibiting autotaxin, GLPG-1690 has the potential to slow down or halt the fibrosis process, improving the quality of life and life expectancy for patients suffering from IPF.
Additionally, given its mechanism of action, GLPG-1690 may also have potential applications in other fibrotic diseases where autotaxin plays a role, although further research and clinical trials would be necessary to confirm its efficacy and safety in these contexts.

Upstream product

• 1628265-17-7 2-chloro-4-(4-fluoro-phenyl)-thiazole-5-carbonitrile 
• 1628264-07-2 (6-bromo-2-ethyl-8-methyl-imidazo[1,2-a]pyridin-3-yl)-methyl-amine 
• 1628263-61-5 2-chloro-1-(3-hydroxyazetidin-1-yl)ethane-1-one 
• 952753-59-2 2-amino-4-(4-fluoro-phenyl)-thiazole-5-carbonitrile 
• 4640-67-9 3-(4-fluorophenyl)-3-oxopropionitrile 
• 3430-21-5 5-bromo-3-methyl-pyridin-2-ylamine 

Relevant articles and documents

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.