17-hydroxy-17-pentafluoroethyl-estra-4,9(10)-dien-11-aryl derivatives, method of production thereof and use thereof for the treatment of diseases

Patent metadata

Field	Value
Publication number	US-9717739-B2
Application number	US-201514731232-A
Country	US
Kind code	B2
Filing date	Jun 4, 2015
Priority date	Jul 20, 2009
Publication date	Aug 1, 2017
Grant date	Aug 1, 2017

Abstract

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.

First claim

The invention claimed is:

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 .

Assignees

• Bayer Ip Gmbh

Inventors

• Schwede Wolfgang
• Klar Ulrich
• Moller Carsten
• Rotgeri Andrea
• Bone Wilhelm

Classifications

• A61P5/24

  of the sex hormones · CPC title

• A61P43/00

  Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 · CPC title

• A61P5/36

  Antigestagens · CPC title

• A61P35/00

  Antineoplastic agents · CPC title

• A61P5/00

  Drugs for disorders of the endocrine system · CPC title