Stereoisomerically pure...

Details Stereoisomerically pure... Stereoisomerically pure...

C - Chemistry, Metallurgy

07

F

167/193, 260/21,

C07F 1/00 (2006.01) A61K 31/565 (2006.01) C07J 11/00 (2006.01) C07J 17/00 (2006.01) C07J 51/00 (2006.01)

Patent

CA 1324126

Abstract of the Disclosure This invention relates to a stereoiso- merically pure .DELTA.2 compound of the formula (I): Image (I) wherein: R1 is hydrogen or -(C=0)-R2, wherein: R2 is an organic substituent selected from the group consisting of alkyls, alkenyls, alkynyls, cycloaklyls, cycloalkylalkylenes, haloalkyls, aryls, haloaryls and arylalkylenes, and their product by the process of: (a) reacting the 17.beta.-hydroxy group of 17.beta.- hydroxy-5.alpha.-estr-1-en-3-one with dihydropyran to produce the 3 keto-17.beta.-ether; (b) reducing the 3-keto-17.beta.-ether product of step (a) with lithium in ammonia; (c) reacting the product of step (b) with dialkyl chlorophosphate to produce the 3-substituted phosphates; (d) reducing the produce of step (c) with lithium and ammonia to produce the .DELTA.2-protected-17 .beta.- ether product; (e) hydrolysis of the produce of step (d) to produce the .DELTA.2-17 .beta.-hydroxy compound; (f) oxidizing the 17 .beta.-hydroxy product of step (e) to produce the 17-keto compound; (g) reacting the 17-keto derivative of step (f) with acetylene magneisum halide to produce the compound of formula I where R1 is hydrogen; and (h) optionally reacting the produce of step (g) with an acyl halide or acyl anhydride to produce the compound of formula I wherein R1 is acyl. The invention also relates to a pharmaceutical composition for oral administration comprising a compound of for- mula I and to a method of achieving contraception (fertility-control) in a female mammal. The compound of formula I has antiprogestational activity in a female mammal and is useful in the control of fertil- ity, having substantially no undesirable side effects.

482054

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