Quingestanol acetate

Chemical Name 19-Norpregna-35-dien-20-vn-17-ol-3-(cvclopentvloxy) acetate (17a) Common Name — 

The starting material for the purposes of this discussion is 3-cycloethylenedioxy-10-cyano-17a-ethynyl-19-nor-A -androstene-17/3-ol (I). 

A solution of 10-cyano-3-monoketal (I) in 60 cc of dry ether and 60 ccof dry dioxane is dropped Into 400 cc of liquid ammonia. Then, 1.2 g of lithium in small pieces are introduced over a period of 90 minutes and the mixture is maintained under stirring until the blue color of the solution is discharged. 

To a solution of 1 g of the mixture of 3-ketal-isomers of compound (II) in 10 cc of acetic anhydride is added a solution of 700 mg of p-toluenesulfonic acid in 7 cc of ecetic anhydride. The reaction mixture is kept at room temperature and under stirring for 5 hours. After some time e crystalline product begins to precipitate and the precipitation is complete by diluting with water. The precipitate is filtered and crystallized from methanol to give 17a-ethynvl-19-nor-testosterone 3,17-diecetate (III), melting point 175°C to 17B°C. 

A solution of 1 g of the diacetate (III) in lOOcc of n-heptane containing 2.5 ccof cyclopentanol and 50 mg of p-toluenesulfonic acid is heated under reflux for 20 hours. After cooling, a few drops of pyridine are added and the solvent is eiiminated by evaporation under vacuum. The residue is taken up with methanol to give 3-cyclopentyl enolether of 17a-ethvnyl-19-nortes-tosterone ecetate which, after recrystalllzation from methanol, melts at 182°C to 1B4°C. 

10 g of ammonium chloride are added and the stirring is continued for some hours longer at room temperature. The moist ammonia is left to evaporate cautiously, maintaining the mixture on water-bath and diluting the resulting solution with water. After repeated extractions with ether, an oily residue is obtained consisting of a mixture of A and A isomers of 17a-ethynyl-19-nor-androstene-17 -ol-3-one 3-ethylene ketal (It). 

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Oxyphenisatin acetate Pancuronium bromide Prednisolone acetate Quingestanol acetate Sulfacetamide Testosterone 17/3[Pg.1609]

Quingestanol acetate Stanzolol Tegafur Tiopronin Tocainide Vindesine Xipamid 2oxazo lamina Ammonium acetate Cyclopentamine HCl Ammonium carbonate Aminosalicylic acid Phenytoin... 

Quingestanol acetate Cycloheptanone Heptabarbitol Cyclohexan-1,3-d lone Molindone Cyclohexanone Cyclobutyrol... 

Chlormadinone acetate (500 gg) [141], megestrol acetate (500 gg) [142], norethisterone acetate, norgestrel (50 gg) [140] quingestanol acetate are all currently under study. 

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