496775-62-3

Basic information

• Product Name: Unii-4U07F515lg
• Synonyms: Eltrombopag olamine;Sb 497115gr;Unii-4U07F515lg;3'-[(2Z)-2-[1-(3,4-Dimethylphenyl)-1,5-dihydro-3-methyl-5-oxo-4H-pyrazol-4-ylidene]hydrazinyl]-2'-hydroxy-[1,1'-biphenyl]-3-carboxylic acid compd. with 2-aminoethanol;Revolade;3'-[(2Z)-2-[1-(3,4-DiMethylphenyl)-1,5-dihydro-3-Methyl-5-oxo-4H-pyrazol-4-ylidene]hydrazinyl]-2'-hydroxy-[1,1'-biphenyl]-3-carboxylic acid coMpd. with 2-aMinoethanol(1:2);EltroMbopag diethanolaMine salt;EltroMbopag OlaMine API
• CAS NO: 496775-62-3
• Molecular Formula: C29H36N6O6
• Molecular Weight: 564.63274
• EINECS: 1308068-626-2
• Product Categories: API
• Mol File: 496775-62-3.mol
• Article Data: 0

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: Unii-4U07F515lg(CAS DataBase Reference)
• NIST Chemistry Reference: Unii-4U07F515lg(496775-62-3)
• EPA Substance Registry System: Unii-4U07F515lg(496775-62-3)

Safety Data

• Hazardous Substances Data: 496775-62-3(Hazardous Substances Data)

Usage

Description

Unii-4U07F515lg, also known as Glycerol, is a simple polyol compound that is widely used in various industries due to its unique properties. It is a colorless, odorless, and viscous liquid with a sweet taste. Glycerol is hygroscopic, meaning it can absorb water from the air, and it is also a versatile solvent for various substances. Its chemical formula is C3H8O3, and it is a byproduct of soap and biodiesel production.

Uses

Used in Pharmaceutical Industry:
Unii-4U07F515lg is used as a pharmaceutical agent for the treatment of chemotherapy-induced thrombocytopenia and immune thrombocytopenic purpura. It helps in increasing the platelet count in patients undergoing chemotherapy, which can cause a decrease in platelets due to the toxic effects of the treatment.
Used in Cosmetics and Personal Care Industry:
Glycerol is used as a humectant in the cosmetics and personal care industry. It helps to retain moisture in the skin, hair, and other personal care products, providing hydration and improving the overall texture and appearance.
Used in Food and Beverage Industry:
In the food and beverage industry, Unii-4U07F515lg is used as a sweetener, preservative, and moisturizer. It helps to improve the texture, taste, and shelf life of various food products, including baked goods, confectionery, and beverages.
Used in Industrial Applications:
Glycerol is used in various industrial applications, such as in the production of nitroglycerin, which is an essential component of explosives and propellants. It is also used as a solvent in the manufacturing of inks, dyes, resins, and other chemicals.
Used in Energy Production:
In the energy sector, glycerol is used as a feedstock for the production of biofuels, such as biodiesel. It can also be used as a fuel additive to improve the combustion efficiency and reduce emissions in internal combustion engines.
Used in Agriculture:
Unii-4U07F515lg is used in the agriculture industry as a component in the formulation of fertilizers and soil conditioners. It helps to improve soil structure, water retention, and nutrient availability for plants.

Clinical Use

Eltrombopag olamine, a thrombopoietin receptor (TpoR) agonist, was approved in late 2008 for the once-daily, oral short-term and long-term treatment of adult patients with previously treated chronic idiopathic thrombocytopenic purpura (ITP). It is the first small-molecule TpoR agonist and was launched in the U.S. for this indication in 2009 by GlaxoSmithKline (GSK). Because eltrombopag is a small molecule, the drug is administered orally and has a reduced potential for causing an immune system reaction versus alternative protein-based therapies. In 2010, eltrombopag was approved in Europe for the long-term treatment of adult patients with previously treated chronic ITP.

Synthesis

The synthesis began with the nitration of 2-bromophenol (39) with sodium nitrate and sulfuric acid in water at 10°C to give 2-bromo-6-nitrophenol (40) in 25% yield, which was methylated using methyl iodide and potassium carbonate in refluxing acetone providing 2-bromo- 6-nitroanisole (41) in 76% yield (the Scheme).40 Suzuki coupling of compound 41 with 3-carboxyphenyl boronic acid with Pd(PPh3)4 and 2 M sodium carbonate in refluxing dioxane gave 20-methoxy- 30-nitrobiphenyl-3-carboxylic acid (42) in 47% yield as a tan powder. Demethylation using 48% HBr (aq) in refluxing acetic acid resulted in a 79% yield of 20-hydroxy-30-nitrobiphenyl-3-carboxylic acid (43). The nitro group of compound 43 was reduced via catalytic hydrogenation at 50 psi at room temperature over Pd/C in mixed ethanol/3 M aq NaOH solution to give 30-amino-20-hydroxybiphenyl- 3-carboxylic acid (44) in quantitative yield. The intermediate 1-(3,4-dimethylphenyl)-3-methyl-2,5-dihydro-1Hpyrazol- 5-one (47) was prepared by condensing of 3,4-dimethylphenyl- hydrazine 45 with ethyl acetoacetate 46 with sodium acetate in refluxing acetic acid in 76% yield. Treatment of (44) with sodium nitrite in 1 M HCl at 5°C, followed by condensation with 1-(3,4-dimethylphenyl)-3-methyl-2,5-dihydro-1H-pyrazol-5-one (47) at a constant pH of 7–8 via the addition of sodium bicarbonate and ethanol afforded eltrombopag in 32% yield. Finally, eltrombopag was treated with hydroxyl ethylamine to give eltrombopag olamine (VIII).

InChI:InChI=1/C25H22N4O4.2C2H7NO/c1-14-10-11-19(12-15(14)2)29-24(31)22(16(3)28-29)27-26-21-9-5-8-20(23(21)30)17-6-4-7-18(13-17)25(32)33;2*3-1-2-4/h4-13,26,30H,1-3H3,(H,32,33);2*4H,1-3H2/b27-22-;;