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Claims for Patent: 4,027,019

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Claims for Patent: 4,027,019

Title: 3-Oximes of D-17.alpha.-ethynyl-19-nortestosterone esters and method
Abstract:3-Oximes of D-17.alpha.-ethynyl-19-nortestosterone esters and derivatives thereof have pre- and post-coital activity for the suppression of fertility.
Inventor(s): Shroff; Arvin Pranlal (Piscataway, NJ)
Assignee: Ortho Pharmaceutical Corporation (Raritan, NJ)
Application Number:05/652,000
Patent Claims: 1. A compound in the D series of the formula: ##STR5## wherein R is alkanoyl of from 2 to 10 carbon atoms and R' is a member selected from the group consisting of methyl and ethyl.

2. The compound of claim 1 wherein R' is ethyl.

3. The compound of claim 2 wherein R is caproyl.

4. The compound of claim 2 wherein R is acetyl.

5. The compound of claim 2 wherein R is propionyl.

6. The compound of claim 2 wherein R is decanoyl.

7. The compound of claim 1 wherein R' is methyl.

8. The compound of claim 7 wherein R is acetyl.

9. A method of preparing a compound in the D series of claim 1 of the formula: ##STR6## which comprises reacting a ketone in the D series of formula: ##STR7## with an hydroxylamine hydrohalide in the presence of a base, wherein R is alkanoyl of from 2 to 10 carbon atoms and R' is a member selected from the group consisting of methyl and ethyl.

10. The method as in claim 9, wherein the base is a member selected from the group consisting of pyridine, sodium hydroxide, and sodium acetate.

11. The method of claim 9 wherein the hydroxylamine hydrohalide is hydroxylamine hydrochloride.

12. The method as in claim 9, wherein R is acetyl and R' is ethyl.

13. A method of suppressing fertility comprising administering to a female animal an effective antifertility amount of a compound in the D series of claim 1 of formula: ##STR8## wherein R is alkanoyl of from 2 to 10 carbon atoms and R' is a member selected from the group consisting of methyl and ethyl, whereby fertility is suppressed.

14. The method of claim 13 wherein R is acetyl and R' is ethyl.

15. A composition useful in suppressing fertility comprising a compound in the D series of claim 1 of formula: ##STR9## and an estrogenic hormone, wherein R is alkanoyl of from 2-10 carbon atoms and R' is a member selected from the group consisting of methyl and ethyl.

16. The composition of claim 15 wherein R is acetyl, R' is ethyl and the estrogenic hormone is selected from the group consisting of ethinylestradiol, 17.beta.-estradiol, mestranol and 17.alpha.-ethinylestradiol 3-cyclopentyl ether.

17. The composition of claim 16 wherein the estrogenic hormone is ethinylestradiol.

18. A method of suppressing fertility comprising administering to a female an effective antifertility amount of a composition of claim 15.

19. The method of claim 18 wherein R is acetyl, R' is ethyl and the estrogenic hormone is ethinylestradiol.
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