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ChemicalBook--->CAS DataBase List--->496775-62-3

496775-62-3

496775-62-3 Structure

496775-62-3 Structure
IdentificationBack Directory
[Name]

Unii-4U07F515lg
[CAS]

496775-62-3
[Synonyms]

Revolade
Sb 497115gr
Unii-4U07F515
ELTROMBOPAG OL
Unii-4U07F515lg
Promacta Olamine
Eltrombopag Olamin
Eltrombopag olamine
EltroMbopag IMpurity
Eltrombopag Diolamine
ELTROMBOPAG OLAMINE IH
EltroMbopag OlaMine API
Eltrombopag ethanolamine
EltroMbopag diethanolaMine salt
Unii-4U07F515lg ISO 9001:2015 REACH
ELTROMBOPAG DIETHANOLAMINE SALT; PROMACTA; REVOLADE; SB-497115GR
2-Aminoethanol (E)-3'-(2-(1-(3,4-dimethylphenyl)-3-methyl-5-oxo-1H-pyrazol-4(5H)-ylidene)hydra
2-aminoethanol,3-[(5E)-5-[[2-(3,4-dimethylphenyl)-5-methyl-3-oxo-1H-pyrazol-4-yl]hydrazinylidene]-6-oxocyclohexa-1,3-dien-1-yl]benzoicaci
2-aminoethanol,3-[(5E)-5-[[2-(3,4-dimethylphenyl)-5-methyl-3-oxo-1H-pyrazol-4-yl]hydrazinylidene]-6-oxocyclohexa-1,3-dien-1-yl]benzoic acid
2-aminoethanol (Z)-3'-(2-(1-(3,4-dimethylphenyl)-3-methyl-5-oxo-1H-pyrazol-4(5H)-ylidene)hydrazinyl)-2'-hydroxy-[1,1'-biphenyl]-3-carboxylate
2-aminoethanolhemi((Z)-3'-(2-(1-(3,4-dimethylphenyl)-3-methyl-5-oxo-1H-pyrazol-4(5H)-ylidene)hydrazinyl)-2'-hydroxy-[1,1'-biphenyl]-3-carboxylate)
2-aminoethanol with (Z)-3'-(2-(1-(3,4-dimethylphenyl)-3-methyl-5-oxo-1H-pyrazol-4(5H)-ylidene)hydrazinyl)-2'-hydroxy-[1,1'-biphenyl]-3-carboxylate (2:1)
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
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)
[EINECS(EC#)]

629-876-8
[Molecular Formula]

C25H22N4O4.2(C2H7NO)
[MDL Number]

MFCD30181471
[MOL File]

496775-62-3.mol
[Molecular Weight]

503.56
Chemical PropertiesBack Directory
[storage temp. ]

Keep in dark place,Inert atmosphere,2-8°C
[solubility ]

DMSO:56.33(Max Conc. mg/mL);99.76(Max Conc. mM)
DMF:1.0(Max Conc. mg/mL);1.77(Max Conc. mM)
DMF:PBS (pH 7.2) (1:3):0.25(Max Conc. mg/mL);0.44(Max Conc. mM)
Ethanol:0.1(Max Conc. mg/mL);0.18(Max Conc. mM)
[form ]

Powder
[Stability:]

Hygroscopic
[InChIKey]

LQQUHOUXABUDJA-OUFJFOJPSA-N
[SMILES]

C(N)CO.O=C1/C(/C(C)=NN1C1C=CC(C)=C(C)C=1)=N\NC1C=CC=C(C2C=CC=C(C(=O)O)C=2)C=1O
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H319-H412
[Precautionary statements ]

P264-P280-P305+P351+P338-P337+P313P-P273-P501
Hazard InformationBack Directory
[Description]

Eltrombopag is used to treat low blood platelet counts in adults with chronic immune (idiopathic) thrombocytopenia (ITP), when certain other medicines, or surgery to remove the spleen, have not worked well enough.Eltrombopag has also been recently approved (late 2012) for the treatment of thrombocytopenia (low blood platelet counts) in patients with chronic hepatitis C to allow them to initiate and maintain interferon-based therapy.
[Uses]

Treatment of chemotherapy-induced thrombocytopenia and treatment of immune thrombocytopenic purpura.
[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¨C8 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).

Synthesis_496775-62-3

Spectrum DetailBack Directory
[Spectrum Detail]

Unii-4U07F515lg(496775-62-3)1HNMR
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