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US 2013/0029953 A1Published application
Progesterone antagonists
OwnerKlaus Nickisch, Kesavaram Narkunan +2inventors
InventorsKlaus Nickisch, Kesavaram Narkunan, Baishakhi Debnath, Bindu Santhamma
Life of this patent
Estimating the term…
Abstract
Described herein are compounds which either act as pure antiprogestins or as antiprogestins with partial agonistic activity and methods of treating cancer using such compounds.
Claims18
A compound having the structure of formula (I):
- In which
- R1 is a hydrogen atom, a straight-chain C1-C5 alkyl group, a branched C1-C5 alkyl group, a C1-C5 cycloalkyl group or a halogen atom;
- R2 is a hydrogen atom, a straight-chain C1-C5 alkyl group, a branched C1-C5 alkyl group, a C1-C5 cycloalkyl group or a halogen atom;
- or
- R1 and R2 together are a methylene group,
- R3 is a hydrogen atom, a straight-chain C1-C5 alkyl group, a branched C1-C5 alkyl group, a C1-C5 cycloalkyl group or a halogen atom;
- R4 is a hydrogen atom, a straight-chain C1-C5 alkyl group, a branched C1-C5 alkyl group, a C1-C5 cycloalkyl group or a halogen atom;
- or
- R3 and R4 together are an additional bond or a methylene group,
- R5 is a radical Y or an aryl radical that is optionally substituted with Y,
- Y is a hydrogen atom, a halogen atom, —OR8, —NO2, —N3, —CN, —NR8aR8b, —NHSO2R8, —CO2R8, C1-C10 alkyl, C1-C10 substituted alkyl, C1-C10 cycloalkyl, C1-C10 alkenyl, C1-C10 alkynyl, C1-C10 alkoxy, C1-C10 cycloalkoxy, C1-C10 alkanoyloxy, benzoyloxy, arylacyl, C1-C10-alkylacyl, C1-C10-cycloalkylacyl, C1-C10 hydroxyalkyl, aryl arylalkyl, heteroaryl with two or three heteroatoms, or heteroarylacyl containing up to three heteroatoms;
- R6 is —OH, —OR8, —OC(O)R8, —C≡C—R10, —C(O)CH2R8, alkyl, —H, —(CH2)mCH2R9, or —CH═CH—(CH2)m—R9;
- R7 is —OH, —OR8, —OC(O)R8, —C≡C—R10, —C(O)CH2R8, alkyl, —H, —(CH2)mCH2R9, —CH═CH—(CH2)m—R9;
- a radical of formula CnFmHo where n is 2,3,4,5 or 6 with m≧1 and m+o<2n+1, or —CF2—CH2—CH3;
- or
- R6 and R7 together form
- R8 is H, alkyl, alkyloxy, or aryl;
- R9 is H, cyano, hydroxyl, alkoxy, acyloxy;
- and
- R10 is H, chloro, fluoro, alkyl, hydroxyalkyl;
- wherein the wavy lines represent a substituent in either the α- or β-position.
18 more elements
A method of treating cancer in a subject comprising administering to a subject a medicament comprising an effective amount of a compound having the structure of formula (I):
- In which
- R1 is a hydrogen atom, a straight-chain C1-C5 alkyl group, a branched C1-C5 alkyl group, a C1-C5 cycloalkyl group or a halogen atom;
- R2 is a hydrogen atom, a straight-chain C1-C5 alkyl group, a branched C1-C5 alkyl group, a C1-C5 cycloalkyl group or a halogen atom;
- or
- R1 and R2 together are a methylene group,
- R3 is a hydrogen atom, a straight-chain C1-C5 alkyl group, a branched C1-C5 alkyl group, a C1-C5 cycloalkyl group or a halogen atom;
- R4 is a hydrogen atom, a straight-chain C1-C5 alkyl group, a branched C1-C5 alkyl group, a C1-C5 cycloalkyl group or a halogen atom;
- or
- R3 and R4 together are an additional bond or a methylene group,
- R5 is a radical Y or an aryl radical that is optionally substituted with Y,
- Y is a hydrogen atom, a halogen atom, —OR8, —NO2, —N3, —CN, —NR8aR8b, —NHSO2R8, —CO2R8, C1-C10 alkyl, C1-C10 substituted alkyl, C1-C10 cycloalkyl, C1-C10 alkenyl, C1-C10 alkynyl, C1-C10 alkoxy, C1-C10 cycloalkoxy, C1-C10 alkanoyloxy, benzoyloxy, arylacyl, C1-C10-alkylacyl, C1-C10-cycloalkylacyl, C1-C10 hydroxyalkyl, aryl arylalkyl, heteroaryl with two or three heteroatoms, or heteroarylacyl containing up to three heteroatoms;
- R6 is —OH, —OR8, —OC(O)R8, —C≡C—R10, —C(O)CH2R8, alkyl, —H, —(CH2)mCH2R9, or —CH═CH—(CH2)m—R9;
- R7 is —OH, —OR8, —OC(O)R8, —C≡C—R10, —C(O)CH2R8, alkyl, —H, —(CH2)mCH2R9, —CH═CH—(CH2)m—R9;
- a radical of formula CnFmHo, where n is 2,3,4,5 or 6 with m≧1 and m+o<2n+1, or —CF2—CH2—CH3;
- or
- R6 and R7 together form
- R8 is H, alkyl, alkyloxy, or aryl;
- R9 is H, cyano, hydroxyl, alkoxy, acyloxy;
- and
- R10 is H, chloro, fluoro, alkyl, hydroxyalkyl;
- wherein the wavy lines represent a substituent in either the α- or β-position.
18 more elements
Dependencies are inferred from the claim text.