1151516-14-1

Basic information

• Product Name: RDEA-594 sodiuM
• Synonyms: Lesinurad sodiuM;RDEA-594 sodiuM;Acetic acid, 2-[[5-bromo-4-(4-cyclopropyl-1-naphthalenyl)-4H-1,2,4-triazol-3-yl]thio]-, sodium salt (1:1);sodium 2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)acetate;Acetic acid, 2-((5-bromo-4-(4-cyclopropyl-1-naphthalenyl)-4H-1,2,4-triazol-3-yl)thio)-, sodium salt;Sodium 2-((5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3- yl)sulfanyl)acetate
• CAS NO: 1151516-14-1
• Molecular Formula: C₁₇H₁₃BrN₃O₂S*Na
• Molecular Weight: 426.26279
• Mol File: 1151516-14-1.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: RDEA-594 sodiuM(CAS DataBase Reference)
• NIST Chemistry Reference: RDEA-594 sodiuM(1151516-14-1)
• EPA Substance Registry System: RDEA-594 sodiuM(1151516-14-1)

Safety Data

• Hazardous Substances Data: 1151516-14-1(Hazardous Substances Data)

Usage

General Description

RDEA-594 sodium is a chemical compound that belongs to the class of receptor tyrosine kinase inhibitors. It is specifically designed to target and inhibit the activity of the fibroblast growth factor receptor (FGFR), which is overexpressed in certain cancers and is associated with tumor growth and progression. By blocking the activity of FGFR, RDEA-594 sodium has the potential to inhibit the growth of cancer cells and disrupt tumor progression. It has shown promise in preclinical studies for the treatment of various solid tumors, including breast and gastric cancers, and is currently being investigated in clinical trials for its potential as a targeted therapy for these and other cancer types.

Upstream product

• 1533519-85-5 2-((4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazole-3-yl)thio)acetic acid methyl ester 
• 25033-19-6 1-cyclopropyl-naphthalene 

Downstream Products

• 878672-00-5 (R)-2-((5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetic acid 
• 878672-00-5 (S)-2-((5-bromo-4-(4-cyclopropyl-1-naphthalenyl)-4H-1,2,4-triazol-3-yl)thio)-acetic acid 
• 878672-00-5 2-{[5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl]sulfanyl}acetic acid 

Relevant articles and documents

RESOLUTION METHOD FOR AXIS CHIRAL ENANTIOMERS OF LESINURAD

A resolution method of axial chiral enantiomers of lesinurad (2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)acetic acid) adopts inexpensive and readily available quinoline natural products and derivatives thereof, such as quinine, cinchonine, quinidine or cinconidine as resolving agents to react with lesinurad racemate in an organic solvent to form a salt, and the salt is dissociated by acidification so as to obtain optically pure (R)- or (S)-2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)acetic acid. The method can give axial chiral enantiomer of lesinurad in R configuration with a chiral purity ee of up to 100% and a total yield of 90% or more. The obtained axial chiral enantiomer of lesinurad in S configuration can reach a chiral purity ee of up to 99.9% and a total yield of 80% or more.

Axially chiral enantiomers of drug Lesinurad

The invention discloses an axially chiral R-enantiomer and an axially chiral S-enantiomer of the drug Lesinurad. The axially chiral R-enantiomer shows excellent URAT1 inhibition effect, overcomes the problems that a high dosage of Lesinurad racemate leads to renal toxicity and a low dosage Lesinurad racemate cannot produce additional drug effect, and can be applied to treatment or prevention of symptoms of abnormal tissue uric acid levels.

MANUFACTURE OF 2- (5- BROMO-4 (-CYCLOPROPYLNAPHTHALEN-1-YL) -4H-1,2,4-TRIAZOL-3-YLTHIO) ACETIC ACID

Described herein are certain processes for the synthesis of compounds of Formula (I):