Demegeston

demegestone Chemische Eigenschaften,Einsatz,Produktion Methoden

• Originator

  Lutionex,Roussel,France,1974

• Definition

  ChEBI: Demegestone is a 20-oxo steroid.

• Manufacturing Process

  Step A: Preparation of 3-methoxy-17α-methyl-19-nor-?1,3,5(10)-pregnatriene20-one - Under agitation and an inert atmosphere, 1.150 grams of lithium were introduced into one liter of ammonia cooled to a temperature of -70°C. For 15 minutes this reaction mixture was agitated, then, while maintaining the temperature at about -75°C, one liter of ether were added thereto, followed by 20 grams of 3-methoxy-19-nor-?1,3,5(10),16-pregnatetraene20-one. The mixture was allowed to stand for 2 hours at a temperature of -75°C under continued agitation and under continued inert atmosphere. Next, 160 cc of methyl iodide were added and the reaction mixture was again agitated for 2 hours at -75°C.
  Thereafter, the ammonia was evaporated, 1 liter of water was added thereto and the aqueous phase was separated and extracted with ether. The ethereal phases now combined were washed with water until the wash waters were neutral, then dried over sodium sulfate, filtered and distilled to dryness to obtain 21 grams of product, which was dissolved in 210 cc of ethanol under reflux. Next, 21 cc of acetic acid and 21 grams of Girard's reactant T were added thereto. The mixture was agitated for 1? hours under an atmosphere of nitrogen while maintaining the reflux. Thereafter, the reaction mixture was cooled to room temperature and then poured into 1,050 cc of water. Next, 155 cc of 2 N sodium hydroxide solution were added and finally the mixture was extracted with ether.
  The combined ethereal phases were washed with water until the wash waters were neutral, dried over sodium sulfate, filtered and evaporated to dryness to obtain 16.80 grams of raw product which was purified by redissolving the product obtained in acetone under reflux and by recrystallization by heating and cooling.
  13.185 grams of 3-methoxy-17α-methyl-19-nor-?1,3,5(10)-pregnatriene-20-one were thus obtained in the form of a colorless, solid product. The product was easily soluble in ether, soluble in alcohol, benzene and chloroform and insoluble in water. This product had a melting point of 109°C and a specific rotation of [α]D20 = +75°+/-1° (c = 0.5% in chloroform). The starting compound, 3-methoxy-19-nor-?1,3,5(10),16-pregnatetraene-20-one, was obtained according to the process described by Burn, J. Chem. SOC.1962, page 364.
  13.185 grams of 3-methoxy-17α-methyl-19-nor-?1,3,5(10)-pregnatriene-20-one were thus obtained in the form of a colorless, solid product. The product was easily soluble in ether, soluble in alcohol, benzene and chloroform and insoluble in water. This product had a melting point of 109°C and a specific rotation of [α]D20 = +75°+/-1° (c = 0.5% in chloroform). The starting compound, 3-methoxy-19-nor-?1,3,5(10),16-pregnatetraene-20-one, was obtained according to the process described by Burn, J. Chem. SOC.1962, page 364.
  The aqueous phase was discarded and the combined ethereal phases were washed with water, dried over sodium sulfate, filtered and distilled to dryness, to obtain 20.240 grams of 3-methoxy-17α-methyl-19-nor-?2,5(10)- pregnadiene-20-ol,which product was utilized as such for the next step. The compound occurred in the form of an amorphous product which was soluble in alcohol, ether, benzene and acetone and insoluble in water.
  washed with water, dried over sodium sulfate, filtered and distilled to dryness, to obtain 20.240 grams of 3-methoxy-17α-methyl-19-nor-?2,5(10)- pregnadiene-20-ol,which product was utilized as such for the next step. The compound occurred in the form of an amorphous product which was soluble in alcohol, ether, benzene and acetone and insoluble in water.
  Step D: Preparation of 17α-methyl-19-nor-?5(10)-pregnene-3,20-dione - 20.5 grams of the compound prepared in Step C were dissolved in 615 cc of acetone under an atmosphere of nitrogen and under agitation. The solution obtained was cooled to -20°C. Next 21 cc of a solution of 54 grams of chromic acid anhydride and 46 cc of dilute sulfuric acid were added thereto. Th

• Therapeutic Function

  Progestin

demegestone Upstream-Materialien And Downstream Produkte

Demegeston Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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