1533519-85-5

Basic information

• Product Name: lesinurad int
• Synonyms: lesinurad int;Methyl 2-[[4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl]thio]acetate;Acetic acid, 2-[[4-(4-cyclopropyl-1-naphthalenyl)-4H-1,2,4-triazol-3-yl]thio]-, methyl ester;2-[[4-(4-cyclopropyl-1-naphthalenyl)-4H-1,2,4-triazol-3-yl]thio]-, methyl ester;Lesinurad Impurity 9;Methyl 2-[[4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl]thio]acetate(for Lesinurad);4-triazol-3-yl]thio]acetate;Methyl 2-[[4-(4-cyclopropylnaphthalen-1-yl)-4H-1
• CAS NO: 1533519-85-5
• Molecular Formula: C₁₈H₁₇N₃O₂S
• Molecular Weight: 339.41148
• Mol File: 1533519-85-5.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 546.4±60.0 °C(Predicted)
• Appearance: /
• Density: 1.38±0.1 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• PKA: 0.56±0.10(Predicted)
• CAS DataBase Reference: lesinurad int(CAS DataBase Reference)
• NIST Chemistry Reference: lesinurad int(1533519-85-5)
• EPA Substance Registry System: lesinurad int(1533519-85-5)

Safety Data

• Hazardous Substances Data: 1533519-85-5(Hazardous Substances Data)

Usage

General Description

Lesinurad is a medication used to treat gout by reducing the levels of uric acid in the blood. It works by inhibiting the transporter proteins involved in the reabsorption of uric acid in the kidneys, which leads to increased excretion of the substance in the urine. This helps to prevent the formation of urate crystals in the joints and tissues, which are responsible for the painful symptoms of gout. Lesinurad is typically used in combination with other medications for gout, such as xanthine oxidase inhibitors or uric acid-lowering therapy, to effectively manage the condition. Common side effects of lesinurad include headache, flu-like symptoms, and elevated levels of blood creatinine. It is important for patients to discuss the potential benefits and risks of this medication with their healthcare provider before starting treatment.

Upstream product

• 878671-94-4 1-amino-4-cyclopropylnaphthalene 
• 90-11-9 1-Bromonaphthalene 
• 25033-19-6 1-cyclopropyl-naphthalene 
• 878671-93-3 1-cyclopropyl-4-nitronaphthalene 
• 1533519-87-7 1-amino-4-cyclopropylnaphthalene oxalate 
• 878671-95-5 1-cyclopropylnaphthalene-4-yl isothiocyanate 
• 1533519-92-4 1-amino-4-cyclopropylnaphthalene hydrochloride 
• 1533519-91-3 tert-butyl 4-cyclopropylnaphthalen-1-ylcarbamate 
• 1533519-86-6 N-(4-cyclopropylnaphthalen-1-yl)-2-formylhydrazine-1-thiocarboxamide 
• 1533519-84-4 4-(4-cyclopropylnaphthalen-1-yl)-4Η-1,2,4-triazole-3-thiol 
• 96-32-2 bromoacetic acid methyl ester 
• 2298-07-9 4-Bromo-1-naphthylamine 
• 127971-24-8 1-bromo-4-cyclopropylnaphthalene 
• 24127-59-1 methyl 2-(4H-1,2,4-triazole-3-mercapto)acetate 

Downstream Products

• 878672-00-5 2-{[5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl]sulfanyl}acetic acid 
• 1151516-14-1 2-((5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetic acid sodium salt 
• 878672-00-5 (-)-2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)acetic acid 
• 878672-00-5 (+)-2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)acetic acid 
• 1158970-60-5 2-((5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetic acid potassium salt 
• 1158970-52-5 2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)acetic acid ethyl ester 
• 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.

Preparation method of Lesinurad

The invention discloses a preparation method of Lesinurad, and belongs to the technical field of chemical drug synthesis. A compound of the formula Les-03 in the description is prepared from compoundsshown in formulas Les-01 and Les-02 as raw materials, a compound of the formula Les-04 is added, and a compound of the formula Les-05 is prepared. The compound of the Les-05 has high selectivity during coupling, so that the purity of a reaction product is high, post-treatment is facilitated, and quality of an obtained final product is controllable; the compound in Les-07 is prepared from the compound in Les-05 and the compound in Les-06 by Suzuki coupling reaction, the Suzuki coupling reaction has high reliability and good repeatability, and finally Lesinurad is obtained through protecting group removal. The preparation method has the advantages of short process route, high yield and low cost; adopted reagents are non-toxic or low-toxic conventional reagents, and are basically harmless tooperators and basically pollution-free to the environment; the whole process is simple and convenient to operate, the process stability is good, the quality of the obtained final product is controllable and stable, and the method is suitable for commercial production.

A process for the preparation of intermediates to si Lei (by machine translation)

The invention discloses a compound of formula (I) the method for the preparation of intermediates shows Si Lei. The method can directly introduce triazazole functional group, the reaction yield is up to 96.30%, sulfur generation and avoid the use of toxic reagent such as phosgene. Furthermore, the synthetic route of this invention does not need to ring closing reaction step, a total of six-step reaction of the final product can be obtained, it is simple and convenient to prepare, low cost, is suitable for industrial production. (by machine translation)