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US 2012/0190660 A1Published application
17-hydroxy-17-pentafluoroethyl-estra-4,9(10)-diene-11-ethynylphenyl derivatives, methods for the production thereof and use thereof for treating diseases
AssigneeBayer Pharma Aktiengesellschaft
InventorsUlrich Klar, Wolfgang Schwede, Carsten Möller, Andrea Rotgeri, Wilhelm Bone
Life of this patent
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Abstract
The invention relates to 17-hydroxy-17-pentafluoroethylestra-4,9(10)-diene 11-ethynylphenyl derivatives of the formula I, in which R1 and X are each as defined in the claims and the description, and to a process for preparation thereof and to the use thereof as medicaments.
Claims16
17-Hydroxy-17-pentafluoroethylestra-4,9(10)-diene 11-ethynylphenyl derivatives of the formula I
- in which
- R1 is joined to the phenyl ring in the m or p position via a C—C triple bond and is a —(CH═CH)n—R2, —(CH2)q—R3 or —CH═NOR4 radical,
- R2 is hydrogen or an aryl, C1-C10-alkyl, —CO2R6 or —CN group,
- R3 is hydrogen, NH2, N3 or an —NHCONHR4, —OCONHR4, —OR5 group,
- R4 is selected from the group comprising hydrogen, C1-C10-alkyl, C2-C10-alkenyl, aryl, C7-C20-aralkyl, (CH2)s—R6, CH2—CO—OR6,
- in which
- R5 is selected from the group comprising hydrogen, C7-C20-aralkyl, CH2CO2R6, CH2CN, CH2CH2OH,
- n is 0 to 2,
- q is 1 or 2,
- s is 1 or 2,
- R6 is hydrogen, C1-C10-alkyl, aryl, C7-C20-aralkyl,
- X is oxygen, NOR6 or an NNHSO2R6 group where R6 is as defined above,
- and the salts, solvates or solvates of the salts thereof, including all crystal polymorphs, the α-, β- or γ-cyclodextrin clathrates, and the compounds encapsulated with liposomes.
10 more elements
(8S,11R,13S,14S,17S)-17-hydroxy-11-[4-(3-hydroxyprop-1-yn-1-yl)phenyl]-13-methyl-17-pentafluoroethyl-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
- (E)-5-[4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-pentafluoro ethyl-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-1′-yl)phenyl]pent-2-en-4-ynenitrile
- (Z)-5-[4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-pentafluoro ethyl-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-1′-yl)phenyl]pent-2-en-4-ynenitrile
- (8S,11R,13S,14S,17S)-17-hydroxy-11-{4-[3-(2-hydroxyethoxy)prop-1-yn-1-yl]phenyl}-13-methyl-17-pentafluoroethyl-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
- 3-{(E)-4-[4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-pentafluoro ethyl-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl]but-1-en-3-ynyl}benzoic acid
- {3-[4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-pentafluoro ethyl-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl]prop-2-ynyloxy}acetonitrile
- 4-[4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-pentafluoro ethyl-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenylethynyl]benzoic acid 3-[4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-pentafluoroethyl-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenylethynyl]benzoic acid methyl ester
- (8S,11R,13S,14S,17S)-11-(4-ethynylphenyl)-17-hydroxy-13-methyl-17-pentafluoro ethyl-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydro cyclopenta[a]phenanthren-3-one
- (8S,11R,13S,14S,17S)-11-[4-(3-azidoprop-1-yn-1-yl)phenyl]-17-hydroxy-13-methyl-17-pentafluoro ethyl-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydro cyclopenta[a]phenanthren-3-one
- (E)-[4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-pentafluoro ethyl-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-1′-yl)phenyl]propynal O-benzyl oxime and (Z)-[4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-pentafluoro ethyl-2,3,6,7,8,11,12,13,14,15,16,17-do decahydro-1H-cyclopenta[a]phenanthren-1′-yl)phenyl]propynal O-benzyl oxime
- (E)-[4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-pentafluoroethyl-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl]propynal O-ethyl oxime and (Z)-[4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-pentafluoroethyl-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl]propynal O-ethyl oxime
- [4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-pentafluoro ethyl-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl]propynal O-isobutyl oxime
- 1-(3,5-dimethylisoxazol-4-yl)-3-{3-[4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-pentafluoro ethyl-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl]prop-2-ynyl}urea
- 1-{3-[4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-pentafluoro ethyl-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl]prop-2-ynyl}-3-isopropylurea
- 3-(3-{3-[4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-pentafluoro ethyl-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl]prop-2-ynyl}ureido)propionic acid ethyl ester
- 1-ethyl-3-{3-[4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-pentafluoro ethyl-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl]prop-2-ynyl}urea
- 1-{3-[4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-pentafluoro ethyl-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl]prop-2-ynyl}-3-(4-methoxyphenyl)urea
- 1-{3-[4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-pentafluoro ethyl-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl]prop-2-ynyl}-3-phenylurea
- 1-{3-[4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-pentafluoro ethyl-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl]prop-2-ynyl}-3-(4-fluorophenyl)urea
- 1-benzyl-3-{3-[4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-pentafluoro ethyl-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl]prop-2-ynyl}urea
- 1-allyl-3-{3-[4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-pentafluoro ethyl-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl]prop-2-ynyl}urea
- Allylcarbamic acid 3-[4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-pentafluoro ethyl-2,3,6,7,8,11,12,13,14,15, 16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl]prop-2-ynyl ester
- Ethylcarbamic acid 3-[4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-pentafluoro ethyl-2,3,6,7,8,11,12,13,14,15, 16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl]prop-2-ynyl ester
- Phenylcarbamic acid 3-[4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-pentafluoro ethyl-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl]prop-2-ynyl ester
- 4-methylphenylcarbamic acid 3-[4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-pentafluoro ethyl-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl]prop-2-ynyl ester
- 4-fluorophenylcarbamic acid 3-[4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-pentafluoro ethyl-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl]prop-2-ynyl ester
- Isopropylcarbamic acid 3-[4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-pentafluoro ethyl-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl]prop-2-ynyl ester
- Benzylcarbamic acid 3-[4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-pentafluoro ethyl-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl]prop-2-ynyl ester
- (8S,11R,13S,14S,17S)-17-hydroxy-11-[4-(3-methanesulphonyl-phenylethynyl)phenyl]-13-methyl-17-pentafluoroethyl-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
- 4-methoxyphenylcarbamic acid 3-[4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-pentafluoro ethyl-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl]prop-2-ynyl ester
- 4-{3-[4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-pentafluoro ethyl-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl]prop-2-ynyloxycarbonylamino}benzoic acid ethyl ester
- (4-piperidin-1-ylphenyl)carbamic acid 3-[4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-pentafluoroethyl-2,3,6,7,8,11,12,13,14,15,16,17-Dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl]prop-2-ynyl ester
- (8S,11R,13S,14S,17S)-17-hydroxy-11-[4-(4-methanesulphonylphenylethynyl)phenyl]-3-methyl-17-pentafluoroethyl-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
- 3-pyridylcarbamic acid 3-[4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-pentafluoro ethyl-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl]prop-2-ynyl ester
- Tert-butylcarbamic acid 3-[4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-pentafluoroethyl-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl]prop-2-ynyl ester
31 more elements
15-16. (canceled)
Dependencies are inferred from the claim text.