The invention relates to 17-hydroxy-17-pentafluoroethyl-estra-4,9(10)-dien-11-aryl derivatives of formula I with progesterone-antagonizing action and methods of production thereof, use thereof for the treatment and/or prevention of diseases and use thereof for producing medicinal products for the treatment and/or prevention of diseases, in particular uterine fibroids (myomata, uterine leiomyomata), endometriosis, heavy menstrual bleeding, meningiomata, hormone-dependent breast cancers and menopause-associated complaints or for fertility control and emergency contraception.

Claims

10 · 2 independent · depth 3

10 granted claims

›1.independentA compound of formula I+8

›2.↳ 1Compound according to claim 1 of general formula V:d2

›3.↳ 1Compound according to claim 1 of general formula VId2+1

›5.↳ 1Compound according to claim 1 of general formula VII:d2+1

›8.↳ 1Medicinal product comprising a compound as defined in claim 1 in combination with a pharmaceutically suitable excipient.d2

›9.↳ 1A method of treating uterine fibroids,nendometriosis, heavy menstrual bleeding, meningiomata, or breast cancer comprising the step of administering to…d2

›10.↳ 1A method of contraception comprising the step of administering to a patient in need thereof of a compound according to claim 1.d2

›7.independentA compound selected fromn4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]benzamide;4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluo…

A compound selected fromn4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]benzamide;4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]-N,N-dimethylbenzamide;(11β,17β)-17-hydroxy-11-{4-[(4-methylpiperazin-1-yl)carbonyl]phenyl}-17-(pentafluoroethyl)estra-4,9-dien-3-one;tert-butyl-4-{4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]benzoyl}piperazine-1-carboxylate;(11β,17β)-17-hydroxy-17-(pentafluoroethyl)-11-[4-(piperidin-1-ylcarbonyl)phenyl]estra-4,9-dien-3-one;methyl-1-{4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]benzoyl}piperidine-4-carboxylate;N-[2-(dimethylamino)ethyl]-4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]benzamide;N-[3-(dimethylamino)propyl]-4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]benzamide;N-[2-(dimethylamino)ethyl]-4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]-N-methylbenzamide;methyl-2-({4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]benzoyl}amino)benzoate;4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]-N-(pyridin-2-yl)benzamide;4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]-N-(pyridin-3-yl)benzamide;4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]-N-[3-(morpholin-4-yl)propyl]benzamide;4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]-N-(pyridin-4-yl)benzamide;(11β,17β)-17-hydroxy-17-(pentafluoroethyl)-11-[4-(pyrrolidin-1-ylcarbonyl)phenyl]estra-4,9-dien-3-one;4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]-N-(2-phenylethyl)benzamide;4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]-N-(2-phenylpropan-2-yl)benzamide;4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]-N-(4-sulphamoylbenzyl)benzamide;N-ethyl-4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]benzamide;4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]-N-(pyridin-2-ylmethyl)benzamide;4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]-N-(pyridin-4-ylmethyl)benzamide;4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]-N-phenylbenzamide;4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]-N-(2-methoxyphenyl)benzamide;4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]-N-(3-methoxyphenyl)benzamide;4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]-N-(4-methoxyphenyl)benzamide;N-(4-chlorophenyl)-4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]benzamide;N,N-diethyl-4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]benzamide;4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]-N-methyl-N-phenylbenzamide;(11β,17β)-17-hydroxy-11-[4-(morpholin-4-ylcarbonyl)phenyl]-17-(pentafluoroethyl)estra-4,9-dien-3-one;(11β,17β)-17-hydroxy-17-(pentafluoroethyl)-11-{4-[(4-phenylpiperazin-1-yl)carbonyl]phenyl}estra-4,9-dien-3-one;4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]-N-methyl-N-(pyridin-2-ylmethyl)benzamide;4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]-N-methyl-N-(pyridin-3-ylmethyl)benzamide;4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]-N-methyl-N-(pyridin-4-ylmethyl)benzamide;N-benzyl-4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]benzamide;4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]-N-(4-methoxybenzyl)benzamide;N-(4-chlorobenzyl)-4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]benzamide;N-(2-acetamidoethyl)-4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]benzamide;methyl-4-({4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]benzoyl}amino)benzoate;(11β,17β)-11-[4-(3,4-dihydroisoquinolin-2(1H)-ylcarbonyl)phenyl]-17-hydroxy-17-(pentafluoroethyl)estra-4,9-dien-3-one;(11β,17β)-11-{4-[(4-benzylpiperazin-1-yl)carbonyl]phenyl}-17-hydroxy-17-(pentafluoroethyl)estra-4,9-dien-3-one;N-(4-carbamoylphenyl)-4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]benzamide;N-cyclopropyl-4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]benzamide;4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]-N-methyl-N-(2-phenylethyl)benzamide;(11β,17β)-17-hydroxy-17-(pentafluoroethyl)-11-(4-{[4-(2-phenylethyl)piperazin-1-yl]carbonyl}phenyl)estra-4,9-dien-3-one;(11β,17β)-17-hydroxy-17-(pentafluoroethyl)-11-(4-{[4-(pyridin-4-yl)piperazin-1-yl]carbonyl}phenyl)estra-4,9-dien-3-one;(11β,17β)-17-hydroxy-17-(pentafluoroethyl)-11-(4-{[4-(pyrazin-2-yl)piperazin-1-yl]carbonyl}phenyl)estra-4,9-dien-3-one;(11β,17β)-11-[4-({4-[2-(dimethylamino)ethyl]piperazin-1-yl}carbonyl)phenyl]-17-hydroxy-17-(pentafluoroethyl)estra-4,9-dien-3-one;(11β,17β)-17-hydroxy-17-(pentafluoroethyl)-11-[4-({4-[2-(pyrrolidin-1-yl)ethyl]piperazin-1-yl}carbonyl)phenyl]estra-4,9-dien-3-one;(11β,17β)-17-hydroxy-17-(pentafluoroethyl)-11(4-{[4-(pyridin-4-ylmethyl)piperazin-1-yl]carbonyl}phenyl)estra-4,9-dien-3-one;4-[(11β,17(3)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]-N-methyl-N-[2-(pyridin-2-yl)ethyl]benzamide;N-benzyl-4-[(11β,17(3)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]-N-methylbenzamide;N-(4-acetamidophenyl)-4-[(11β, 17(3)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]benzamide;4-[(11β,17(3)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]-N-(3-methoxybenzyl)benzamide;4-[(11β,17(3)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]-N-[2-(pyrrolidin-1-yl)ethyl]benzamide;4-[(11β,17(3)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]-N-[2-(pyridin-3-yl)ethyl]benzamide;N-(3-chlorobenzyl)-4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]benzamide;methyl-3-({4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]benzoyl}amino)benzoate;4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]-N-methyl-N-[2-(pyridin-4-yl)ethyl]benzamide;N-(cyclopropylmethyl)-4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]benzamide;4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]-N-[4-(phenylcarbamoyl)phenyl]benzamide;4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]-N-[2-(pyridin-2-yl)ethyl]benzamide;4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]-N-[2-(4-methylpiperazin-1-yl)ethyl]benzamide;(11β,17β)-17-hydroxy-17-(pentafluoroethyl)-11-{4-[(4-phenylpiperidin-1-yl)carbonyl]phenyl}estra-4,9-dien-3-one;4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]-N-[2-(pyridin-4-yl)ethyl]benzamide;(11β,17β)-11-{4-[(4-benzoylpiperazin-1-yl)carbonyl]phenyl}-17-hydroxy-17-(pentafluoroethyl)estra-4,9-dien-3-one;4-{4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]benzoyl}-N,N-dimethylpiperazine-1-carboxamide;(11β,17β)-17-hydroxy-11-(4-{[4-(methylsulphonyl)piperazin-1-yl]carbonyl}phenyl)-17-(pentafluoroethyl)estra-4,9-dien-3-one;(11β,17β)-17-hydroxy-17-(pentafluoroethyl)-11-(4-{[4-(pyridin-2-ylmethyl)piperazin-1-yl]carbonyl}phenyl)estra-4,9-dien-3-one;(11β,17β)-17-hydroxy-17-(pentafluoroethyl)-11-(4-{[4-(pyridin-3-ylmethyl)piperazin-1-yl]carbonyl}phenyl)estra-4,9-dien-3-one;methyl-4-{4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]benzoyl}piperazine-1-carboxylate;2-(4-{4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]benzoyl}piperazin-1-yl)-N-methylacetamide;4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]-N-methyl-N-[2-(pyridin-3-yl)ethyl]benzamide;(11β,17β)-17-hydroxy-17-(pentafluoroethyl)-11-[4-(piperazin-1-ylcarbonyl)phenyl]estra-4,9-dien-3-one;(11β,17β)-11-{4-[(4-acetylpiperazin-1-yl)carbonyl]phenyl}-17-hydroxy-17-(pentafluoroethyl)estra-4,9-dien-3-one;1-{4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]benzoyl}piperidine-4-carboxylic acid;2-({4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]benzoyl}amino)benzoic acid;3-({4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]benzoyl}amino)benzoic acid;4-({4-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]benzoyl}amino)benzoic acid; and4⬲-[(11β,17β)-17-hydroxy-3-oxo-17-(pentafluoroethyl)estra-4,9-dien-11-yl]biphenyl-4-carboxamide;or a salt thereof.

Classifications

9 codes

IPC · International Patent Classification

Section A — Human necessities

A61K31/567
A61K31/58

Section C — Chemistry; metallurgy

C07J43/00
C07J41/00
C07J1/00

USPC · US Patent Classification

514/179552/648514/176540/113

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related publication	US 20130072464 A1	21 Mar 2013

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