Amadinone
Amadinone Basic information
- Product Name:
- Amadinone
- Synonyms:
-
- 6-Chloro-17-hydroxy-19-norpregna-4,6-diene-3,20-dione
- 19-Norpregna-4,6-diene-3,20-dione, 6-chloro-17-hydroxy-
- CAS:
- 30781-27-2
- MF:
- C20H25ClO3
- MW:
- 348.86
- Mol File:
- 30781-27-2.mol
Amadinone Chemical Properties
- Boiling point:
- 509.5±50.0 °C(Predicted)
- Density
- 1.27±0.1 g/cm3(Predicted)
- pka
- 12.86±0.60(Predicted)
Amadinone Usage And Synthesis
Originator
Amadinone,ZYF Pharm Chemical
Uses
Progestin.
Manufacturing Process
A solution of 250.0 mg of δ4-3,20-dioxo-6α,7α-oxido-17α-acetoxy-19-
norpregnene in 15 ml of 1 N hydrochloric acid in dioxan is kept for 1 h at
25°C, then poured into water and neutralized with sodium bicarbonate
solution. The precipitated crude product is dissolved in a 5:1 mixture of ether
and methylene chloride, washed with water until the washings run neutral,
and the solution is dried and evaporated under vacuum to give the δ4-3,20-
dioxo-6-chloro-7α-hydroxy-17α-acetoxy-19-nor-pregnene.
The crude δ4-3,20-dioxo-6-chloro-7α-hydroxy-17α-acetoxy-19-nor-pregnene is
dissolved in 3 ml of pyridine, mixed at 5°-0°C with 0.3 ml of
methanesulphonyl chloride while being stirred, and the mixture is kept for 2
days at 10°C. The reaction product is then poured into dilute sodium
bicarbonate solution, dissolved in ether, and the ethereal solution is washed
until the washings run neutral, dried and evaporated under vacuum and the
δ4-3,20-dioxo-6-chloro-7α-mesyloxy-17α-acetoxy-19-norpregnene is obtained.
The δ4-3,20-dioxo-6-chloro-7α-mesyloxy-17α-acetoxy-19-norpregnene is
dissolved in 25 ml of dimethyl formamide, mixed with 4.5 g of anhydrous
sodium acetate, and the whole is heated for 75 min at 85°C under nitrogen
while being stirred. The cooled reaction mixture is diluted with water,
extracted with a 5:1-mixture of ether and methylene chloride, and the organic
layer is washed with 100 ml of water, dried and evaporated. The resulting
crude product is dissolved in benzene and chromatographed on 15 times its
own weight of alumina (activity II). The afore-mentioned solvent elates 105.0
mg of pure δ4,6-3,20-dioxo-6-chloro-17α-acetoxy-19-norpregnadiene, melting
point 159°-161°C (recrystallized from methylene chloride:hexane).
The δ4,6-3,20-dioxo-6-chloro-17-hydroxy-19-norpregnadien, melting point
159°-161°C, may be produced by hydrolysis of δ4,6-3,20-dioxo-6-chloro-17α-
acetoxy-19-norpregnadiene.
Therapeutic Function
Progestin