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

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)

Upstream product

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

Downstream Products

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

Resolving method of medicine lesinurad axial chiral enantiomer

The invention discloses a resolving method of a medicine lesinurad axial chiral enantiomer. An alkamine derivative with optical activity is used as a resolving agent and reacts with a lesinurad racemic body in an organic solvent to form salts; the salts are dissociated to obtain (R)- or (S)-2-(5-bromo-4-(4-cyclopropylnaphthalene-1-yl-4H-1,2,4-triazole-3-sulfenyl)acetic acid with optical activity is obtained. By the method, an S configuration axial chiral enantiomer and an R configuration axial chiral enantiomer with the optical activity ee reaching 93 percent or higher can be obtained.

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.

Optically pure thioacetic compound

The invention belongs to the field of pharmacy and relates to an optically pure thioacetic compound and application thereof to medicine. The optically pure thioacetic compound comprises levorotatory 2-(5-bromo-4-(4-cyclopropyl-naphthalene-1-base)-4H-1,2,4-triazole-3-based sulfenyl) acetic acid and dextral 2-(5-bromo-4-(4-cyclopropyl-naphthalene-1-base)-4H-1,2,4-triazole-3-based sulfenyl) acetic acid.

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):

POLYMORPHIC, CRYSTALLINE AND MESOPHASE FORMS OF SODIUM 2-(5-BROMO-4-(4-CYCLOPROPYLNAPHTHALEN-1-YL)-4H-1,2,4-TRIAZOL-3-YLTHIO)ACETATE, AND USES THEREOF

Crystalline polymorphs and solid mesophase forms of sodium 2-(5-bromo-4- (4-cyclopropylnaphthalen-l-yl)-4H-l,2,4-triazol-3-ylthio)acetate are described. In addition, pharmaceutical compositions and uses of such compositions for the treatment of a variety of diseases and conditions are provided.