18-Methyl-19-norandrost-4-ene 17, 17-spiro ether (18-methyl-19-nor-20-spirox-4-en-3-one), and pharmaceutical products comprising the same

1. An 18-Methyl-15β,16β-methylene-19-nor-20-spirox-4-en-3-one of formula I

in which

Z is an oxygen atom, two hydrogen atoms, a group ═NOR or ═NNHSO 2 R,

R is a hydrogen atom or a straight- or branched-chain alkyl group having 1 to 4 carbon atoms,

R 4 is a hydrogen atom, a halogen atom or a trifluoromethyl group, and

R 6 and/or R 7 may have α or β configuration, and

R 6 and R 7 are independently of one another a hydrogen atom or a straight- or branched-chain alkyl group having 1 to 4 carbon atoms or a straight- or branched-chain alkenyl group having 2 to 4 carbon atoms or a saturated cycloalkyl group having 3 to 5 carbon atoms or together are a methylene group or a double bond.

2. A compound of claim 1 , which is

18-methyl-15β,16β-methylene-19-nor-20-spiroxa-4,6-dien-3-one,

18-methyl-15β,16β-methylene-19-nor-20-spirox-4-en-3-one,

18-methyl-6β,7β,15β,16β-dimethylene-19-nor-20-spirox-4-en-3-one,

18-methyl-6α,7α,15β,16β-dimethylene-19-nor-20-spirox-4-en-3-one,

18-methyl-15β,16β-methylene-7α-propyl-19-nor-20-spirox-4-en-3-one,

18-methyl-15β,16β-methylene-7β-propyl-19-nor-20-spirox-4-en-3-one,

7α,18-dimethyl-15β,16β-methylene-19-nor-20-spirox-4-en-3-one,

7β,18-dimethyl-15β,16β-methylene-19-nor-20-spirox-4-en-3-one,

7α-ethyl-18-methyl-15β,16β-methylene-19-nor-20-spirox-4-en-3-one,

7β-ethyl-18-methyl-15β,16β-methylene-19-nor-20-spirox-4-en-3-one,

7α-ethenyl-18-methyl-15β,16β-methylene-19-nor-20-spirox-4-en-3-one,

7β-ethenyl-18-methyl-15β,16β-methylene-19-nor-20-spirox-4-en-3-one,

7α-cyclopropyl-18-methyl-15β,16β-methylene-19-nor-20-spirox-4-en-3-one,

7β-cyclopropyl-18-methyl-15β,16β-methylene-19-nor-20-spirox-4-en-3-one,

4,18-dimethyl-15β,16β-methylene-19-nor-20-spirox-4-en-3-one,

4-chloro-18-methyl-15β,16β-methylene-19-nor-20-spirox-4-en-3-one,

4,18-dimethyl-6β,7β,15β,16β-dimethylene-19-nor-20-spirox-4-en-3-one,

4,18-dimethyl-6α,7α,15β,16β-dimethylene-19-nor-20-spirox-4-en-3-one,

4-chloro-18-methyl-6β,7β,15β,16β-dimethylene-19-nor-20-spirox-4-en-3-one, or

4-chloro-18-methyl-6α,7α,15β,16β-dimethylene-19-nor-20-spirox-4-en-3-one.

3. A pharmaceutical product comprising at least one compound as claimed in claim 1 and a pharmaceutically acceptable carrier.

4. The pharmaceutical product as claimed in claim 3 , additionally comprising at least one estrogen.

5. The pharmaceutical product as claimed in claim 4 comprising ethinylestradiol.

6. The pharmaceutical product as claimed in claim 4 , comprising a natural estrogen.

7. The pharmaceutical product as claimed in claim 6 , comprising estradiol.

8. The pharmaceutical product as claimed in claim 6 , comprising estradiol valerate.

9. The pharmaceutical product as claimed in claim 6 , comprising at least one conjugated estrogen.

10. A pharmaceutical product comprising at least one compound as claimed in claim 2 and a pharmaceutically acceptable carrier.

11. The pharmaceutical product as claimed in claim 10 , additionally comprising at least one estrogen.

12. A compound of claim 1 , wherein R is a hydrogen atom or a straight- or branched-chain alkyl group having 3 to 4 carbon atoms.

13. A compound of claim 1 , wherein R 6 and R 7 are independently of one another a hydrogen atom or a straight- or branched-chain alkyl group having 3 to 4 carbon atoms or a straight- or branched-chain alkenyl group having 3 to 4 carbon atoms or a saturated cycloalkyl group having 3 to 5 carbon atoms or together are a methylene group or a double bond.

14. A compound of claim 12 , wherein R 6 and R 7 are independently of one another a hydrogen atom or a straight- or branched-chain alkyl group having 3 to 4 carbon atoms or a straight- or branched-chain alkenyl group having 3 to 4 carbon atoms or a saturated cycloalkyl group having 3 to 5 carbon atoms or together are a methylene group or a double bond.

15. An 18-Methyl-15β,16β-methylene-19-nor-20-spirox-4-en-3-one of formula I

in which

Z is an oxygen atom,

R is a hydrogen atom or a straight- or branched-chain alkyl group having 1 to 4 carbon atoms,

R 4 is a hydrogen atom, a halogen atom or a trifluoromethyl group, and

R 6 and/or R 7 may have α or β configuration, and

R 6 and R 7 are independently of one another a hydrogen atom or a straight- or branched-chain alkyl group having 1 to 4 carbon atoms or a straight- or branched-chain alkenyl group having 2 to 4 carbon atoms or a saturated cycloalkyl group having 3 to 5 carbon atoms or together are a methylene group or a double bond.

16. A compound of claim 15 , wherein R is a hydrogen atom or a straight- or branched-chain alkyl group having 3 to 4 carbon atoms.

17. A compound of claim 15 , wherein R 6 and R 7 are independently of one another a hydrogen atom or a straight- or branched-chain alkyl group having 3 to 4 carbon atoms or a straight- or branched-chain alkenyl group having 3 to 4 carbon atoms or a saturated cycloalkyl group having 3 to 5 carbon atoms or together are a methylene group or a double bond.

18. A compound of claim 16 , wherein R 6 and R 7 are independently of one another a hydrogen atom or a straight- or branched-chain alkyl group having 3 to 4 carbon atoms or a straight- or branched-chain alkenyl group having 3 to 4 carbon atoms or a saturated cycloalkyl group having 3 to 5 carbon atoms or together are a methylene group or a double bond.

19. A pharmaceutical product comprising at least one compound as claimed in claim 15 and a pharmaceutically acceptable carrier.

20. The pharmaceutical product as claimed in claim 19 , additionally comprising at least one estrogen.