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ChemicalBook--->CAS DataBase List--->101975-10-4

101975-10-4

101975-10-4 Structure

101975-10-4 Structure
IdentificationBack Directory
[Name]

ZARDAVERINE
[CAS]

101975-10-4
[Synonyms]

ZARDAVERINE
ZARDAVENINE
3-[4-(difluoromethoxy)-3-methoxyphenyl]-1H-pyridazin-6-one
6-[4-(DIFLUOROMETHOXY)-3-METHOXYPHENYL]-3(2H)-PYRIDAZINONE
3-[4-(difluoromethoxy)-3-methoxy-phenyl]-1H-pyridazin-6-one
3(2H)-Pyridazinone, 6-[4-(difluoromethoxy)-3-methoxyphenyl]-
[Molecular Formula]

C12H10F2N2O3
[MDL Number]

MFCD00867059
[MOL File]

101975-10-4.mol
[Molecular Weight]

268.22
Chemical PropertiesBack Directory
[density ]

1.38±0.1 g/cm3(Predicted)
[storage temp. ]

Store at RT
[solubility ]

DMSO : 100 mg/mL (372.83 mM; Need ultrasonic)
[form ]

Off-white to yellow solid.
[pka]

10.89±0.40(Predicted)
[color ]

White to light yellow
[CAS DataBase Reference]

101975-10-4
Safety DataBack Directory
[WGK Germany ]

3
Hazard InformationBack Directory
[Originator]

Zardaverine,ZYF Pharm Chemical
[Uses]

Bronchodilator;Phosphodiesterase III inhibitor
[Definition]

ChEBI: A pyridazinone derivative in which pyridazin-3(2H)-one is substituted at C-6 with a 4-(difluoromethoxy)-3-methoxyphenyl group. It is a phosphodiesterase inhibitor, selective for PDE3 and 4.
[Manufacturing Process]

20.8 g of 4-hydroxy-3-methoxyacetophenone are dissolved in 350 ml of dioxane and 350 ml of water by the addition of 30.0 g of sodium hydroxide, and the resulting solution is heated to 60°C. While stirring continuously, chlorodifluoromethane is passed into the solution until uptake of the gas stops (about 4 h). The solution is cooled, and the resulting precipitate is filtered off with suction and washed three times with 40 ml of diethyl ether each time. The solution is diluted with water to twice its volume and likewise extracted three times with 100 ml of diethyl ether each time. The combined ether extracts are dried over magnesium sulfate and evaporated in vacuum; the residue is crystallized from petroleum ether (boiling point 50°-70°C), 19.0 g (70.4% of theory) of 4-difluoromethoxy-3-methoxyacetophenone are obtained, melting point 68°C.
15.0 g of 4-difluoromethoxy-3-methoxyacetophenone are heated with 5.9 g of glyoxylic acid monohydrate at 110°C for 2 h. The melt is then cooled to 60°C, 30 ml of water are added, and dissolution is brought about by addition of 10 ml of concentrated aqueous ammonium solution. 3.2 g of hydrazine hydrate are added, and the mixture is boiled under reflux for 2 h, during which the title compound gradually crystallizes out. After cooling, the precipitate is filtered off with suction, thoroughly washed with water, dried and recrystallized from isopropanol. 10.8 g (58.1% of theory) of the 6-(4- difluoromethoxy-3-methoxyphenyl)-3(2H)pyridazinone are obtained, melting point 204°C.
[Therapeutic Function]

Bronchodilator, Anti-asthmatic
[Biological Activity]

Phosphodiesterase inhibitor, selective for PDE3 and 4 (IC 50 values are 0.5 and 0.8 μ M respectively). Also available as part of the Phosphodiesterase Inhibitor Tocriset™ .
[storage]

Store at -20°C
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