GPLG0634

Base Information

• Chemical Name: GPLG0634
• CAS No.: 1206161-97-8
• Molecular Formula: C21H23N5O3S
• Molecular Weight: 425.511
• Hs Code.: 2921309990
• Mol file: 1206161-97-8.mol

Synonyms:GPLG0634;GLPG0634;SYN1158;CyclopropanecarboxaMide, N-[5-[4-[(1,1-dioxido-4-thioMorpholinyl)Methyl]phenyl][1,2,4]triazolo[1,5-a]pyridin-2-yl]-;GLPG0634 (analog);N-[5-[4-[(1,1-Dioxido-4-thiomorpholinyl)methyl]phenyl][1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide;Filgotinib (GLPG0634);N-[5-[4-[(1,1-Dioxido-4-thiomorpholinyl)methyl]phenyl][1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide Filgotinib (GLPG0634)

Chemical Property of GPLG0634

Chemical Property:

• PKA: 8.04±0.20(Predicted)
• Density: 1.51±0.1 g/cm3(Predicted)
• Storage Temp.: -20°C
• Solubility.: Soluble in DMSO (15 mg/ml with warming)

Purity/Quality:

98% ^*data from raw suppliers

GLPG-0634(Filgotinib) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Filgotinib (GLPG0634) is a selective JAK1 inhibitor with IC50 of 10 nM, 28 nM, 810 nM, and 116 nM for JAK1, JAK2, JAK3, and TYK2, respectively. Filgotinib is a JAK1 inhibitor (IC50 = 10 nM). It is selective for JAK1 over JAK3 (IC50 = 810 nM) but also inhibits JAK2 and tyrosine kinase 2 (Tyk2; IC50s = 28 and 116 nM, respectively), as well as Abl, FLT1, -3, and -4, FMS, Mer, and TBK1 activity by greater than 35% in a panel of 177 tyrosine kinases at 1 μM. Filgotinib inhibits IL-6-induced phosphorylation of STAT1 in CD4+ T cells with an IC50 value of 629 nM in isolated human whole blood. It reduces hind paw macrophage and T cell infiltration and bone erosion in a rat model of collagen-induced arthritis when administered at doses ranging from 0.1 to 30 mg/kg per day for 15 days.
• Uses: GLPG-0634 (Filgotinib) is a potent, selective JAK1 inhibitor. Used as an anti-inflammatory agent, it reduces levels of inflammatory cytokines in the bones and tissue of mammals.

Technology Process of GPLG0634

There total 30 articles about GPLG0634 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

thiomorpholine 1,1-dioxide (39093-93-1) + cyclopropanecarboxylic acid [5-(4-bromomethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-amide (1206163-59-8) → N-(5-{4-[(1,1-dioxo-1λ6-thiomorpholin-4-yl)methyl]phenyl}-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide (1206161-97-8)

Guidance literature:

With diisopropylamine; In methanol; dichloromethane; at 20 ℃; for 16h; Reagent/catalyst; Temperature; Inert atmosphere;

Reference yield: 94.3%

C25H27N5O4S → N-(5-{4-[(1,1-dioxo-1λ6-thiomorpholin-4-yl)methyl]phenyl}-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide (1206161-97-8)

Guidance literature:

With ammonium hydroxide; In ethanol; at 20 ℃; Reagent/catalyst; Solvent;

Reference yield: 91.2%

5-[4-(1,1-dioxothiomorpholin-4-ylmethyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (1257705-09-1) + cyclopropanecarboxylic acid chloride (4023-34-1) → N-(5-{4-[(1,1-dioxo-1λ6-thiomorpholin-4-yl)methyl]phenyl}-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide (1206161-97-8)

Guidance literature:

With 4-methyl-morpholine; In 1,4-dioxane; at 50 ℃; for 4h; Reagent/catalyst; Solvent; Temperature; Green chemistry;

upstream raw materials:

thiomorpholine 1,1-dioxide

cyclopropanecarboxylic acid [5-(4-bromomethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-amide

cyclopropanecarboxylic acid [5-(4-hydroxymethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-amide

2-Amino-6-bromopyridine

Refernces

• 1、 -. "PROCESSES FOR THE PREPARATION OF FILGOTINIB". . . Retrieved 2020/03/09.
• 2、 -. "Synthesis method of JAK1 inhibitor Filgotinib". Paragraph 0062-0064; 0073-0077. . Retrieved 2019/10/01.