(8S,9R,10S,11S,13S,14S,16S,17R)-9-fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 4.7 g (12.0 mmole) of 9-fluoro-16β-methyl-11β,17,21-trihydroxypregna-1,4-diene-3,20-dione in 50% acetic acid (600 ml) was stirred with 18 g of sodium bismuthate at room temperature for 2 hours. The brown suspension was filtered through a bed of deactivated silica powder and washed with 100 ml of 50% acetic acid. The filtrate was concentrated in vacuo to 100 ml, diluted with 100 ml of 20% hydrochloric acid and extracted with chloroform. The chloroform solution was washed with 20% hydrochloric acid and water, dried over anhydrous Na2SO4 and evaporated in vacuo to give a solid. This was dissolved in chloroform and chromatographed on a 30 g silica gel column, eluting successively with chloroform and 1:4 ethyl acetate-chloroform to give 2.6 g of the title compound, melting point 281°-283° C., dec. The brown suspension was filtered through a bed of deactivated silica powder washed with 100 ml of 50% acetic acid The filtrate was concentrated in vacuo to 100 ml diluted with 100 ml of 20% hydrochloric acid extracted with chloroform The chloroform solution was washed with 20% hydrochloric acid and water dried over anhydrous Na2SO4 evaporated in vacuo to give a solid chromatographed on a 30 g silica gel column eluting successively with chloroform and 1:4 ethyl acetate-chloroform

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 4.7 g (12.0 mmole) of 9-fluoro-16β-methyl-11β,17,21-trihydroxypregna-1,4-diene-3,20-dione in 50% acetic acid (600 ml) was stirred with 18 g of sodium bismuthate at room temperature for 2 hours. The brown suspension was filtered through a bed of deactivated silica powder and washed with 100 ml of 50% acetic acid. The filtrate was concentrated in vacuo to 100 ml, diluted with 100 ml of 20% hydrochloric acid and extracted with chloroform. The chloroform solution was washed with 20% hydrochloric acid and water, dried over anhydrous Na2SO4 and evaporated in vacuo to give a solid. This was dissolved in chloroform and chromatographed on a 30 g silica gel column, eluting successively with chloroform and 1:4 ethyl acetate-chloroform to give 2.6 g of the title compound, melting point 281°-283° C., dec. The brown suspension was filtered through a bed of deactivated silica powder washed with 100 ml of 50% acetic acid The filtrate was concentrated in vacuo to 100 ml diluted with 100 ml of 20% hydrochloric acid extracted with chloroform The chloroform solution was washed with 20% hydrochloric acid and water dried over anhydrous Na2SO4 evaporated in vacuo to give a solid chromatographed on a 30 g silica gel column eluting successively with chloroform and 1:4 ethyl acetate-chloroform

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Eight rabbits of the New Zealand breed were used, weighing approximately 2 kg. In the right eye of each animal, 0.8 ml/week of Bentelan Depot (equivalent to 4 mg betametasone) were instilled for 4 weeks. The left eye was kept as control. The medicament, administered subconjunctivally, brought about an increase of the intraocular tension in the first week, reached its peak in the second week and then remained constant until the fifth week. an increase of the intraocular tension in the first week remained constant until the fifth week

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Eight rabbits of the New Zealand breed were used, weighing approximately 2 kg. In the right eye of each animal, 0.8 ml/week of Bentelan Depot (equivalent to 4 mg betametasone) were instilled for 4 weeks. The left eye was kept as control. The medicament, administered subconjunctivally, brought about an increase of the intraocular tension in the first week, reached its peak in the second week and then remained constant until the fifth week. an increase of the intraocular tension in the first week remained constant until the fifth week

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 4.7 g (12.0 mmole) of 9-fluoro-16β-methyl-11β,17,21-trihydroxypregna-1,4-diene-3,20-dione in 50% acetic acid (600 ml) was stirred with 18 g of sodium bismuthate at room temperature for 2 hours. The brown suspension was filtered through a bed of deactivated silica powder and washed with 100 ml of 50% acetic acid. The filtrate was concentrated in vacuo to 100 ml, diluted with 100 ml of 20% hydrochloric acid and extracted with chloroform. The chloroform solution was washed with 20% hydrochloric acid and water, dried over anhydrous Na2SO4 and evaporated in vacuo to give a solid. This was dissolved in chloroform and chromatographed on a 30 g silica gel column, eluting successively with chloroform and 1:4 ethyl acetate-chloroform to give 2.6 g of the title compound, melting point 281°-283° C., dec. The brown suspension was filtered through a bed of deactivated silica powder washed with 100 ml of 50% acetic acid The filtrate was concentrated in vacuo to 100 ml diluted with 100 ml of 20% hydrochloric acid extracted with chloroform The chloroform solution was washed with 20% hydrochloric acid and water dried over anhydrous Na2SO4 evaporated in vacuo to give a solid chromatographed on a 30 g silica gel column eluting successively with chloroform and 1:4 ethyl acetate-chloroform