9 alpha, 11 beta-substituted and 11 beta-substituted estranes

Abstract

9 alpha, 11 beta and 11 beta-substituted estranes are disclosed which exhibit elevated estrogenic and postcoital contraceptive activities. A process for their manufacture and their use in pharmaceuticals is also disclosed.

What is claimed is: 
     
       1. A compound of the formula ##STR7## wherein R 1  is selected from the group consisting of hydrogen, lower alkyl, cycloalkyl and lower acyl; and R 3  is lower alkoxyl.   
     
     
       2. The compound of claim 1 wherein R 1  is acetyl. 
     
     
       3. A compound of the formula ##STR8## wherein R 1  is selected from the group consisting of hydrogen, lower alkyl, cycloalkyl and lower acyl; and R 5  is selected from the group consisting of lower alkyl and hydrogen.   
     
     
       4. The compound of claim 3 having the formula ##STR9## wherein R 1  is selected from the group consisting of hydrogen, lower alkyl, cycloalkyl and lower acyl. 
     
     
       5. The compound of claim 4 having the formula ##STR10## 
     
     
       6. The compound of claim 3 wherein R 5  is a lower alkyl. 
     
     
       7. The compound of claim 6 having the formula ##STR11## 
     
     
       8. A compound of the formula ##STR12## wherein R 1  is selected from the group consisting of hydrogen, lower alkyl, cycloalkyl and lower acyl; and R 5  is a lower alkyl.   
     
     
       9. A compound of the formula ##STR13## wherein R 1  is a selected from the group consisting of hydrogen, lower alkyl, cycloalkyl and lower acyl; R 3  is selected from the group consisting of hydrogen, hydroxyl and lower alkoxy;   R 4  is a pair of substituents the α one of which being selected from hydrogen and lower alkynyl, and the β one of which being selected from alkanoic acid esters, lower alkyl and hydroxyl; and   R 5  is selected from the group consisting of lower alkyl and hydrogen, subject to the proviso that if R 4  is an α .[.hydroxyl.]. .Iadd.hydrogen .Iaddend.and a β alkanoic acid ester or .[.hydrogen,.]. .Iadd.hydroxyl .Iaddend.then R 5  must be a lower alkyl.   
     
     
       10. A compound of the formula ##STR14## wherein R 1  is selected from the group consisting of hydrogen, lower alkyl, cycloalkyl, and lower acyl; R 3  is selected from the group consisting of hydrogen, hydroxyl, and lower alkoxy; and   R 5  is lower alkyl.   
     
     
       11. The compound of claim 10 having the formula ##STR15## wherein R 1  is selected from the group consisting of hydrogen, lower alkyl, cycloalkyl, and lower acyl; and R 5  is a lower alkyl.   
     
     
       12. The compound of claim 11 having the formula ##STR16## 
     
     
       13. A compound of claim 9 of the formula ##STR17## wherein R 1  is selected from the group consisting of hydrogen, lower alkyl, cycloalkyl and lower acyl; R 4  is a pair of substituents, the α one of which being a lower alkynyl and the β one of the which being a hydroxyl; and   R 5  is a lower alkyl.   
     
     
       14. A compound of claim 13 of the formula ##STR18## wherein R 4  is a pair of substitutents the α one of which being a lower alkynyl and the β one of which being a hydroxyl. 
     
     
       15. The compound of claim 14 having the formula ##STR19## 
     
     
       16. The compound of claim 9 wherein R 4  is an α hydrogen and a α lower alkyl and R 3  is hydroxyl. 
     
     
       17. The compound of claim 16 wherein R 5  is a lower alkyl. 
     
     
       18. The compound of claim 16 wherein R 5  is hydrogen. 
     
     
       19. The compound of claim 18 having the formula ##STR20## 
     
     
       20. The compound of claim 9 where in R 4  is an α alkynyl and a β lower alkanoic acid ester. 
     
     
       21. The compound of claim 16 having the formula ##STR21## wherein R 1  is selected from the group consisting of hydrogen, lower alkyl, cycloalkyl and lower acyl. 
     
     
       22. The compound of claim 21 having the formula ##STR22## 
     
     
       23. A pharmaceutical composition useful for producing an estrogenic effect in a female mammal which comprises an effective estrogenic amount of a compound of claim 3 in admixture with a pharmaceutically acceptable excipient. 
     
     
       24. A pharmaceutical composition useful for producing a contraceptive effect in a female mammal which comprises an effective contraceptive amount of a compound of claim 3 in admixture with a pharmaceutically acceptable excipient. 
     
     
       25. A method of treating a female mammal to achieve an estrogenic effect therein which comprises administering to said mammal an effective estrogenic amount of the pharmaceutical composition of claim 23. 
     
     
       26. A method of treating a female mammal to achieve a contraceptive effect therein which comprises administering to said mammal an effective contraceptive amount of the pharmaceutical composition of claim 24. 
     
     
       27. A pharmaceutical composition useful for producing an estrogenic effect in a female mammal which comprises an effective estrogenic amount of a compound of claim 10 in admixture with a pharmaceutically acceptable excipient. 
     
     
       28. A pharmaceutical composition useful for producing a contraceptive effect in a female mammal which comprises an effective contraceptive amount of a compound of claim 10 in admixture with a pharmaceutically acceptable excipient. 
     
     
       29. A pharmaceutical composition useful for producing an estrogenic effect in a female mammal which comprises an effective estrogenic amount of a compound of claim 12 in admixture with a pharmaceutically acceptable excipient. 
     
     
       30. A pharmaceutical composition useful for producing a contraceptive effect in a female mammal which comprises an effective contraceptive amount of a compound of claim 12 in admixture with a pharmaceutically acceptable excipient. 
     
     
       31. A pharmaceutical composition useful for producing an estrogenic effect in a female mammal which comprises an effective estrogenic amount of a compound of claim 13 in admixture with a pharmaceutically acceptable excipient. 
     
     
       32. A pharmaceutical composition useful for producing a contraceptive effect in a female mammal which comprises an effective contraceptive amount of a compound of claim 13 in admixture with a pharmaceutically acceptable excipient. 
     
     
       33. A pharmaceutical composition useful for producing an estrogenic effect in a female mammal which comprises an effective estrogenic amount of a compound of claim 15 in admixture with a pharmaceutically acceptable excipient. 
     
     
       34. A pharmaceutical composition useful for producing a contraceptive effect in a female mammal which comprises an effective contraceptive amount of a compound of claim 15 in admixture with a pharmaceutically acceptable excipient. .Iadd. 
     
     
       35.  A compound of the formula ##STR23## wherein R 1  is selected from the group consisting of hydrogen, lower alkyl, cycloalkyl and lower acyl; R 3  is selected from the group consisting of hydrogen, hydroxyl and lower alkoxy;   R 4  a pair of substituents the alpha one of which being selected from hydrogen and lower alkynyl, and the beta one of which being selected from alkanoic acid ester lower alkyl and hydroxyl; and   R 5  is selected from the group consisting of lower alkyl and hydrogen, subject to the proviso that if R 3  is a hydroxyl and R 4  is an alpha hydrogen and a beta alkanoic acid ester or hydrogen, then R 5  must be a lower alkyl. .Iaddend. .Iadd.   
     
     
       36.  The compound of claim 35 wherein R 1  is hydrogen,   R 3  is hydrogen,   R 4  is a pair of substituents the alpha one of which is hydrogen and the beta one of which is hydroxyl, and   R 5  is hydrogen. .Iaddend.