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ChemicalBook--->CAS DataBase List--->1154028-82-6

1154028-82-6

1154028-82-6 Structure

1154028-82-6 Structure
IdentificationBack Directory
[Name]

Molidustat(BAY 85-3934)
[CAS]

1154028-82-6
[Synonyms]

CS-1728
MOLIDUSTAT
Somatoprim
BAY 85-3934
Molidustat(BAY 85-3934)
BAY 85-3934;BAY-85-3934
2-(6-morpholin-4-ylpyrimidin-4-yl)-4-(triazol-1-yl)-1H-pyrazol-3-one
2-(6-morpholinopyrimidin-4-yl)-4-(1H-1,2,3-triazol-1-yl)-1H-pyrazol-3(2H)-one
1,2-dihydro-2-[6-(4-morpholinyl)-4-pyrimidinyl]-4-(1H-1,2,3-triazol-1-yl)-3H-pyrazol-3-one
2-[6-(4-Morpholinyl)-4-pyrimidinyl]-4-(1H-1,2,3-triazol-1-yl)-1,2-dihydro-3H-pyrazol-3-one
2-[6-(Morpholin-4-yl)pyrimidin-4-yl]-4-(1H-1,2,3-triazol-1-yl)-1,2-dihydro-3H-pyrazol-3-one
3H-Pyrazol-3-one, 1,2-dihydro-2-[6-(4-morpholinyl)-4-pyrimidinyl]-4-(1H-1,2,3-triazol-1-yl)-
[EINECS(EC#)]

815-038-0
[Molecular Formula]

C13H14N8O2
[MDL Number]

MFCD28411428
[MOL File]

1154028-82-6.mol
[Molecular Weight]

314.3
Chemical PropertiesBack Directory
[Boiling point ]

589.2±60.0 °C(Predicted)
[density ]

1.67±0.1 g/cm3(Predicted)
[storage temp. ]

Store at -20°C
[solubility ]

insoluble in EtOH; insoluble in H2O; ≥5.68 mg/mL in DMF
[form ]

solid
[pka]

5.38±0.37(Predicted)
[color ]

White to off-white
[InChI]

InChI=1S/C13H14N8O2/c22-13-10(20-2-1-16-18-20)8-17-21(13)12-7-11(14-9-15-12)19-3-5-23-6-4-19/h1-2,7-9,17H,3-6H2
[InChIKey]

IJMBOKOTALXLKS-UHFFFAOYSA-N
[SMILES]

N1C=C(N2C=CN=N2)C(=O)N1C1C=C(N2CCOCC2)N=CN=1
Hazard InformationBack Directory
[Description]

Hypoxia-inducible factor (HIF) is the major transcription factor involved in erythropoietin gene expression. Because oxygen-dependent degradation of the α subunit of HIF suppresses erythropoietin expression, stimulation of erythropoiesis by agents that prevent degradation of HIF has been one strategy for managing anemia. BAY 85-3934 stabilizes HIF from degradation in the proteasome by inhibiting HIF-1α prolyl hydroxylase (IC50 = 0.49 μM). Inhibition of HIF prolyl hydroxylase by BAY 85-3934 has been shown to increase endogenous production of erythropoietin. This compound has been investigated in clinical trial for treatment of patients with anemia associated with chronic kidney disease and/or end-stage renal disease.
[Uses]

Molidustat (BAY 85-3934) is an orally active inhibitor of hypoxia-inducible factor prolyl hydroxylase (HIF-PH) with IC50 values of 480 nM, 280 nM, and 450 nM for PHD1, PHD2, and PHD3, respectively. Molidustat can elevate the levels of circulating erythropoietin (EPO) to near-normal physiological ranges. Molidustat can be utilized in the research of renal anemia[1][2].
[Synthesis]

4-(6-Hydrazino-4-pyriMidinyl)Morpholine, 96%

5767-36-2

3-(Dimethylamino)-2-(1H-1,2,3-triazol-1-yl)acrylic acid methyl ester

1021869-28-2

Molidustat(BAY 85-3934)

1154028-82-6

Example 23: 10.0 g (51.2 mmol) of 4-(6-hydrazinopyrimidin-4-yl)morpholine and 10.7 g (53.8 mmol) of 3-(dimethylamino)-2-(1H-1 ,2,3-triazol-1-yl)methyl acrylate were suspended in 100 mL of n-butyl acetate, 2.92 g (25.6 mmol) of trifluoroacetic acid was added, and the reaction was carried out at reflux temperature (about 120 °C) and the reaction was stirred for 6 hours. Upon completion of the reaction, the reaction mixture was cooled to 20 °C and stirring was continued for 16 h, followed by stirring at 0 °C for 1 h and filtration. The resulting solid was washed twice with cold ethyl acetate (4 mL each time) and dried under reduced pressure at 40 °C. The solid (15.5 mL) was then washed with cold ethyl acetate. The dried solid (15.6 g) was suspended in 100 mL of water, 2.4 mL of acetic acid was added and stirred at 50 °C for 30 min. After cooling to 20 °C, the suspension was filtered, the solid was washed twice with water (10 mL each time) and dried under reduced pressure at 40 °C to afford 13.9 g of the target product, 2-(6-morpholinopyrimidin-4-yl)-4-(1H-1,2,3-triazol-1-yl)-1,2-dihydro-3H-pyrazol-3-one, in 86.3% (as theoretical) yield and 99.7 purity Area%, and 99.0 wt%.

[in vitro]

the ic50 values were found to be dependent on the 2-oxoglutarate concentration in the reaction buffer. by lowering the 2-oxoglutarate concentration from 20 μm to 0.3 μm, the potency of the test compound increased up to 10-fold. variation of the concentrations of fe2+ and ascorbate in the reaction buffer by factors of 30 and 200, respectively, did not alter the potency of the inhibitor by more than 2-fold [1].
[in vivo]

in repeat dosing of bay 85-3934, hemoglobin levels were increased compared with animals in vehicle group, while endogenous epo remained within the normal physiological range. bay 85-3934 therapy was also effective in the treatment of renal anemia in rats with impaired kidney function and, unlike treatment with rhepo, resulted in normalization of hypertensive blood pressure in a rat model of ckd [1].
[IC 50]

480 nm, 280 nm, and 450 nm for phd1, phd2, and phd3, respectively.
[References]

[1] flamme i, oehme f, ellinghaus p, jeske m, keldenich j, thuss u. mimicking hypoxia to treat anemia: hif-stabilizer bay 85-3934 (molidustat) stimulates erythropoietin production without hypertensive effects. plos one. 2014 nov 13;9(11):e111838.
Spectrum DetailBack Directory
[Spectrum Detail]

Molidustat(BAY 85-3934)(1154028-82-6)MS
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