1202757-89-8

Basic information

• Product Name: AVL-292
• Synonyms: AVL-292;LMK-435;N-[3-[[5-Fluoro-2-[[4-(2-methoxyethoxy)phenyl]amino]-4-pyrimidinyl]amino]phenyl]-2-propenamide;2-Propenamide, N-[3-[[5-fluoro-2-[[4-(2-methoxyethoxy)phenyl]amino]-4-pyrimidinyl]amino]phenyl]-;CC-292 (AVL-292);CC-292,LMK-435;N-[3-[[5-Fluoro-2-[[4-(2-methoxyethoxy)phenyl]amino]-4-pyrimidinyl]amino]phenyl]-2-propenamide AVL292;CC-292
• CAS NO: 1202757-89-8
• Molecular Formula: C₂₂H₂₂FN₅O₃
• Molecular Weight: 423.4401832
• Product Categories: Inhibitors
• Mol File: 1202757-89-8.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Density: 1.322±0.06 g/cm3(Predicted)
• Solubility: ≥21.15 mg/mL in DMSO; insoluble in H2O; ≥4.9 mg/mL in EtOH with gentle warming and ultrasonic
• PKA: 13.22±0.70(Predicted)
• CAS DataBase Reference: AVL-292(CAS DataBase Reference)
• NIST Chemistry Reference: AVL-292(1202757-89-8)
• EPA Substance Registry System: AVL-292(1202757-89-8)

Safety Data

• Hazardous Substances Data: 1202757-89-8(Hazardous Substances Data)

Usage

Description

AVL-292 is an orally available, selective, and irreversible inhibitor of Bruton's tyrosine kinase (BTK), a non-receptor tyrosine kinase involved in signal transduction pathways regulating the proliferation, activation, and differentiation of B cells. It targets and covalently binds to BTK at cysteine-481, thereby preventing its activity and exhibiting therapeutic significance in the treatment of B cell-related cancers and autoimmune diseases.

Uses

Used in Oncology:
AVL-292 is used as a targeted therapy for B cell-related cancers such as non-Hodgkin’s lymphoma and B cell chronic lymphocytic leukemia. Its ability to inhibit BTK activity helps control the proliferation and survival of malignant B cells.
Used in Autoimmune Diseases:
AVL-292 is used as a treatment for autoimmune diseases like rheumatoid arthritis. It has been shown to inhibit osteoclast function and reduce osteoclast-stimulated proliferation of multiple myeloma cells in animal models, demonstrating its potential in managing diseases where B cells play a significant role.
Used in Multiple Sclerosis:
AVL-292 is also used in the treatment of multiple sclerosis, another disease where B cells are implicated. Its inhibitory effect on BTK may help reduce the autoimmune response and alleviate disease symptoms.

Upstream product

• 1202759-91-8 N⁴-(3-aminophenyl)-5-fluoro-N²-(4-(2-methoxyethoxy)phenyl)pyrimidine-2,4-diamine 
• 814-68-6 acryloyl chloride 
• 33311-29-4 4-(2-methoxyethoxy)aniline 
• 1202759-90-7 tert-butyl (3-((5-fluoro-2-((4-(2-methoxyethoxyl)phenyl)amino) pyrimidin-4-yl)amino)phenyl)carbamate 
• 1202759-89-4 tert-butyl (3-((2-chloro-5-fluoropyrimidin-4-yl)amino)phenyl)carbamate 
• 99-09-2 3-nitro-aniline 
• 18437-64-4 tert-butyl (3-nitrophenyl)carbamate 
• 528882-15-7 N-methyl-(3-nitrophenyl)carbamic acid tert-butyl ester 
• 528882-16-8 (3-amino-phenyl)-methyl-carbamic acid tert-butyl ester 
• 16230-24-3 Ν-(3-aminophenyl)prop-2-enamide 

Downstream Products

• 1360053-81-1 N-(3-(5-fluoro-2-(4-(2-methoxyethoxyl)phenylamino)pyrimidin-4-ylamino)phenyl)acrylamide besylate 
• 1616380-55-2 3-((3-((5-fluoro-2-((4-(2-methoxyethoxyl)phenyl)amino)pyrimidin-4-yl)amino)phenyl)amino)-2-hydroxy-3-oxopropyl methanesulfonate 
• 1616380-43-8 N-(3-((5-fluoro-2-((4-(2-methoxyethoxyl)phenyl)amino)pyrimidin-4-yl)amino)phenyl)oxirane-2-carboxamide 

Relevant articles and documents

Synthesis of N-(3-(5-fluoro-2-(4-(2-methoxyethoxy)phenylamino)pyrimidin-4-ylamino)phenyl)acrylamide

A method for preparing BTK inhibitor CC-292 of formula 1, comprising: (1) contacting a compound of formula 2 with a compound of formula 3 to obtain a compound of formula 4; (2) contacting the compound of formula 4 with a compound of formula 5 to obtain a

HETEROARYL COMPOUNDS AND USES THEREOF

The present invention provides compounds, pharmaceutically acceptable compositions thereof, and methods of using the same.