Synthesis
Using dienolone acetate (Ⅰ) as a raw material and acetone as a solvent, potassium permanganate was added at room temperature under formic acid catalysis for oxidation reaction. After the reaction was completed, the mixture was filtered and concentrated under reduced pressure to obtain compound (Ⅱ). Compound (Ⅱ) was condensed with acetophenone at room temperature in the presence of perchloric acid. After the reaction was completed, the mixture was concentrated under pressure to obtain compound (Ⅲ). Compound (Ⅲ) was hydrolyzed with potassium hydroxide methanol solution at room temperature and concentrated under reduced pressure to obtain 3-acetyl group to yield 3-hydroxyl group (Ⅳ). Compound (Ⅳ) was oxidized with chromium trioxide in methanol solvent, refluxed with toluene for 1 h, and purified by cooling crystallization to obtain the target compound phenylprogesterone (Ⅴ).
Originator
Neolutin Depo, Medici ,Italy ,1982
Uses
Algestone Acetophenide is a progestational steroid that has been shown to increase the proteins in milk and serum in goats and decrease the weight gain of kids. Algestone Acetophenide is used as an injectable steroid contraceptive in Chile and Mexico.
Definition
ChEBI: Algestone acetophenide is a 16alpha,17alpha-dihydroxyprogesterone acetophenide. It has a role as an anti-inflammatory drug and a synthetic oral contraceptive.
Manufacturing Process
To a suspension of 500 mg of 16α,17α-dihydroxyprogesterone in 25 ml of
freshly redistilled acetophenone is added 0.125 ml of 72% perchloric acid and
the mixture is agitated at room temperature for one hour. The clear solution is
washed with dilute sodium bicarbonate to remove excess acid and the
acetophenone layer, after addition of chloroform is separated from the
aqueous phase. The organic layer is dried over sodium sulfate and after
removal of the chloroform and acetophenone in high vacuum the residue is
crystallized from 95% alcohol. The pure acetophenone derivative has a
melting point of about 142°C to 144°C.
brand name
Deladroxone
(Bristol-Myers Squibb); Droxone (Bristol-Myers
Squibb).
Therapeutic Function
Progestin, Contraceptive
