17-hydroxy-17-pentafluoroethyl-estra-4,9(10)-dien-11-aryl derivatives, method of production thereof and use thereof for the treatment of diseases
View Patent ↗The invention relates to 17-hydroxy-17-pentafluoroethyl-estra-4,9(10)-dien-11-aryl derivatives of Formula I with progesterone antagonizing action and method of production thereof, use thereof for the treatment and/or prophylaxis of diseases and use thereof for the production of medicinal products for the treatment and/or prophylaxis of diseases, in particular of fibroids of the uterus (myomas, uterine leiomyoma), endometriosis, heavy menstrual bleeds, meningiomas, hormone-dependent breast cancers and complaints associated with the menopause or for fertility control and emergency contraception.
1. A compound of formula I
in which
R 1 stands either for a residue Y or for a phenyl ring substituted once or twice with a residue Y,
Y is S(O)(NH)R 3 or S(O) 2 NR 9 R 10 ,
R 3 stands for C 1 -C 6 -alkyl,
X denotes an oxygen atom,
R 9 , R 10 independently of one another are each hydrogen, C 1 -C 6 -alkyl or aryl where aryl is phenyl or a stereoisomer or a salt, thereof.
2. The compound according to claim 1 , in which R 1 represents S(O)(NH)R 3 and X represents O and the separate stereoisomers thereof.
3. The compound according to claim 2 , in which R 3 represents C 1 -C 6 -alkyl and the separate stereoisomers thereof.
4. The compound according to claim 3 , in which R 3 represents methyl and the separate stereoisomers thereof.
5. The compound according to claim 1 , in which R 3 represents C 1 -C 6 -alkyl.
6. A compound according to claim 1 selected from the group consisting of:
(11β, 17β)-17-hydroxy-11-[4-(RS-methylsulphonimidoyl)phenyl]-17-(pentafluoroethyl)estra-4,9-dien-3-one;
(11β, 17β)-17-hydroxy-11-[4′-(RS-methylsulphonimidoyl)biphenyl-4-yl]-17-(pentafluoroethyl)estra-4,9-dien-3-one;
4′-[(11β, 17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-den-11-yl]-N,N-dimethylbiphenyl-4-sulphonamide; and
4-[(11β, 17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]-N,N-dimethylbenzene sulphonamide.
7. A pharmaceutical composition comprising a compound as defined in claim 1 and another active substance.
8. A pharmaceutical composition comprising a compound as defined in claim 1 and an inert, non-toxic, pharmaceutically suitable excipient.
9. A method of treatment of heavy menstrual bleeds, meningiomas, or for fertility control, comprising administering to a subject in need thereof an effective amount of a compound of claim 1 .
10. A method of treatment of fibroids of the uterus comprising administering to a subject in need thereof an effective amount of a compound of claim 1 .
11. A method of treatment of endometriosis comprising administering to a subject in need thereof an effective amount of a compound of claim 1 .
12. A method of treatment of heavy menstrual bleeds, meningiomas, hormone-dependent breast cancers or for fertility control comprising administering to a subject in need thereof an effective amount of a pharmaceutical composition of claim 7 .
13. A method of treatment of fibroids of the uterus comprising administering to a subject in need thereof an effective amount of a pharmaceutical composition of claim 7 .
14. A method of treatment of endometriosis comprising administering to a subject in need thereof an effective amount of a pharmaceutical composition of claim 7 .