18-methyl-19-nor-17-pregn-4-ene-21,17-carbolactones, as well as pharmaceutical preparations that contain the latter
View Patent ↗A 18-Methyl-19-nor-17-pregn-4-ene-21,17-carbolactone of general formula I in which Z, R 4 , R 6 , R 7 are as defined below with the proviso that the compound is not 18-Methyl-15β,16β-methylene-3-oxo-19-nor-17-pregn-4-ene-21,17-carbolactone.
1. A 18-Methyl-19-nor-17-pregn-4-ene-21,17-carbolactone of general formula I
in which
Z means an oxygen atom,
R 4 is a hydrogen atom,
R 6 and R 7 can be in α- or β-position, and, independently of one another, mean a straight-chain or branched-chain alkyl group with 1 to 4 carbon atoms, or
R 6 means a hydrogen atom, and R 7 means an α- or β-position, straight-chain or branched-chain alkyl group with 1 to 4 carbon atoms, or
R 6 and R 7 each mean a hydrogen atom, or
R 6 and R 7 together mean an α- or β-position methylene group or an additional bond,
with the proviso that the compound is not 18-Methyl-15β,16β-methylene-3-oxo-19-nor-17-pregn-4-ene-21,17-carbolactone.
2. A compound of general formula I according to claim 1 , in which R 6 stands for a hydrogen atom, and R 7 stands for a methyl group.
3. A compound of general formula I according to claim 1 , in which R 6 stands for a hydrogen atom and R 7 stands for a propyl group.
4. A compound of general formula I according to claim 1 , in which R 6 and R 7 together stand for a methylene group.
5. A compound of general formula I according to claim 1 , in which R 6 and R 7 together stand for a double bond.
6. A compound of claim 1 , wherein R 6 or R 7 is of 3-4 carbon atoms.
7. A compound of general formula I according to claim 1 , in which R 6 and R 7 can be in α- or β-position, and, independently of one another, mean a straight-chain or branched-chain alkyl group with 1 to 4 carbon atoms.
8. A compound selected from the group consisting of
18-Methyl-15β,16β-methylene-3-oxo-19-nor-17-pregna-4,6-diene-21,17-carbolactone
18-Methyl-6α, 7α-15β,16β-dimethylene-3-oxo-19-nor-17-pregn-4-ene-21,17-carbolactone
18-Methyl-6β,7β-15β,16β-dimethylene-3-oxo-19-nor-17-pregn-4-ene-21,17-carbolactone
7α,18-Dimethyl-15β,16β-methylene-3-oxo-19-nor-17-pregn-4-ene-21,17-carbolactone
7β,18-Dimethyl-15β,16β-methylene-3-oxo-19-nor-17-pregn-4-ene-21,17-carbolactone
7α-Ethyl-18-methyl-15β,16β-methylene-3-oxo-19-nor-17-pregn-4-ene-21,17-carbolactone
7β-Ethyl-18-methyl-15β,16β-methylene-3-oxo-19-nor-17-pregn-4-ene-21,17-carbolactone
18-Methyl-15β,16β-methylene-3-oxo-7α-propyl-19-nor-17-pregn-4-ene-21,17-carbolactone and
18-Methyl-15β,16β-methylene-3-oxo-7β-propyl-19-nor-17-pregn-4-ene-21,17-carbolactone.
9. A 18-Methyl-19-nor-17-pregn-4-ene-21,17-carbolactone of general formula I
in which
Z means an oxygen atom,
R 4 is a hydrogen atom,
R 6 and/or R 7 can be in α- or β-position, and R 6 and R 7 , independently of one another, mean a hydrogen atom or a straight-chain or branched-chain alkyl group with 1 to 4 carbon atoms or together a methylene group or a double bond,
with the proviso that the compound is not 18-Methyl-15β,16β-methylene-3-oxo-19-nor-17-pregn-4-ene-21,17-carbolactone.
10. A compound of general formula I according to claim 9 , in which
R 6 and R 7 , independently of one another, mean a hydrogen atom or a straight-chain or branched-chain alkyl group with 1 to 4 carbon atoms.
11. A pharmaceutical preparation comprising at least one compound according to claim 1 and a pharmaceutically acceptable vehicle.
12. A pharmaceutical preparation according to claim 11 , in addition containing at least one estrogen.
13. A pharmaceutical preparation according to claim 12 , containing ethinyl estradiol.
14. A pharmaceutical preparation according to claim 12 , containing a natural estrogen.
15. A pharmaceutical preparation according to claim 14 , containing estradiol.
16. A pharmaceutical preparation according to claim 14 , containing estradiol valerate.
17. A pharmaceutical preparation according to claim 14 , containing at least one conjugated estrogen.
18. A method of hormone replacement therapy comprising administering to a subject in need thereof an effective amount of a compound of claim 1 .
19. A method of contraception comprising administering to a subject in need thereof an effective amount of a preparation of claim 12 .
20. A method of contraception or hormone replacement therapy comprising administering to a subject in need thereof an effective amount of a compound of claim 8 , wherein in case of hormone replacement therapy an estrogen is also administered.