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Iguratimod

Iguratimod Structure
Iguratimod
  • CAS No.123663-49-0
  • Chemical Name:Iguratimod
  • CBNumber:CB91011295
  • Molecular Formula:C17H14N2O6S
  • Formula Weight:374.37
  • MOL File:123663-49-0.mol
Iguratimod Property
  • Melting point: :238.0 to 242.0 °C
  • Boiling point: :580.6±60.0 °C(Predicted)
  • Density  :1.52±0.1 g/cm3(Predicted)
  • storage temp.  :Inert atmosphere,2-8°C
  • pka :5.58±0.20(Predicted)
  • FDA UNII :4IHY34Y2NV
Hazard and Precautionary Statements (GHS)
  • Symbol(GHS)
  • Signal word
  • Hazard statements
  • Precautionary statements
Iguratimod Price More Price(2)
  • Brand: TCI Chemical
  • Product number: I0945
  • Product name : Iguratimod
  • Purity: >98.0%(HPLC)(T)
  • Packaging: 25mg
  • Price: $50
  • Updated: 2021/03/22
  • Buy: Buy
  • Brand: TCI Chemical
  • Product number: I0945
  • Product name : Iguratimod
  • Purity: >98.0%(HPLC)(T)
  • Packaging: 250mg
  • Price: $289
  • Updated: 2021/03/22
  • Buy: Buy

Iguratimod Chemical Properties,Usage,Production

  • Description

    In August 2011, China’s State FDA approved Simcere Pharmaceutical Group’s new drug application for iguratimod (T-614), a disease modifying anti-rheumatic drug (DMARD) for the treatment of rheumatoid arthritis (RA). Preclinical in vivo studies indicated that iguratimod was effective in an established adjuvant-induced arthritis model (ED40=3.6 mg/kg) in rats and also efficacious in a type II collagen-induced arthritis model in DBA/1J mice at 30 mg and 100 mg/kg.

  • Originator Toyama (Japan)
  • Uses Iguratimod acts as an anti-inflammatory agent, used primarily in the treatment of rheumatoid arthritis.
  • brand name Iremod
  • Clinical Use Iguratimod, which was discovered by Toyama Pharmaceuticals and jointly co-developed with Eisai in Japan, was approved by the PMDA (Pharmaceuticals and Medical Devices Agency) of Japan on June 29, 2012 for the treatment of rheumatoid arthritis. This drug was also independently developed by Simcere Pharmaceutical Group and is marked as Iremod® in China. The drug exhibited inhibitory effects on granuloma inflammation, and was shown to be efficacious for the prevention of joint destruction in adjuvant arthritis.
  • Chemical Synthesis Several synthesis of iguratimod have been published, the most likely scale synthesis, which does not require chromatographic purification, is described in the scheme.The synthesis began with commercially available 3-nitro-4-chloro anisole (78) which was reacted with potassium phenoxide (generated from phenol and potassium t-butoxide at 110 oC) to provide the corresponding nitrophenyl ether which was subsequently reduced and sulfonylated to furnish sulfonamide 79. Next, this diphenyl ether was subjected to a Friedel-Crafts reaction with aminoacetonitrile hydrochloride which gave rise to aminomethylacetophenone 80 in 90% yield. This aminoketone was then formylated with formic trimethylacetic anhydride 81 at room temperature to afford formamide 82 in 91% yield, and this material was immediately subjected to O-demethylation conditions with aluminum trichloride and sodium iodide in acetonitrile to give the phenol 83 in 95% yield. Finally, treatment of the aminomethyl acetophenone phenol 83 with N,N-dimethylformamide dimethylacetal in DMF at low temperatures furnished iguratimod (XII) in 87% yield.

Iguratimod Preparation Products And Raw materials
Raw materials
Preparation Products
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123663-49-0, IguratimodRelated Search:
  • IGURATIMOD
  • iguratimod( R&D)
  • T 614
  • N-[7-methanesulfonamido-4-oxo-6-(phenoxy)chromen-3-yl]formamide
  • 3-(Formylamino)-7-(methylsulfonylamino)-6-phenoxy-4H-1-benzopyran-4-one
  • N-[3-(Formylamino)-4-oxo-6-phenoxy-4H-1-benzopyran-7-yl]methanesulfonamide
  • IguratiMod (T 614)
  • N-(7-(MethylsulfonaMido)-4-oxo-6-phenoxy-4H-chroMen-3-yl)forMaMide
  • CS-1961
  • N-[7-(methanesulfonamido)-4-oxo-6-phenoxy-1-benzopyran-3-yl]formamide
  • Iguratimod &gt
  • Methanesulfonamide, N-[3-(formylamino)-4-oxo-6-phenoxy-4H-1-benzopyran-7-yl]-
  • N-(3-Formamido-4-oxo-6-phenoxy-4H-chromen-7-yl)methanesulfonamide
  • N-[7-(Methanesulfonamido)-4-oxo-6-phenoxy-4H-chromen-3-yl]formamide
  • Iguratimod USP/EP/BP
  • 123663-49-0
  • Pharmaceutical intermediate
  • Pharmaceuticals
  • API