Substituted Pyrrole Derivative

(i) 1-{[6-Chloro-5-(hydroxymethyl)pyridin-3-yl]methyl}-4-(4-cyanophenyl)-2,5-dimethyl-1H-pyrrole-3-carbonitrile,

• (ii) 1-{[6-chloro-5-(hydroxymethyl)pyridin-3-yl]methyl}-4-(4-cyanophenyl)-2-ethyl-5-methyl-1H-pyrrole-3-carbonitrile,
• (iii) 1-{[6-chloro-5-(hydroxymethyl)pyridin-3-yl]methyl}-4-(4-cyanophenyl)-5-methyl-2-propyl-1H-pyrrole-3-carbonitrile,
• (iv) 1-{[6-chloro-5-(hydroxymethyl)pyridin-3-yl]methyl}-4-(4-cyanophenyl)-2-cyclopropyl-5-methyl-1H-pyrrole-3-carbonitrile,
• (v) 1-{[6-chloro-5-(hydroxymethyl)pyridin-3-yl]methyl}-4-(3-cyanophenyl)-2,5-dimethyl-1H-pyrrole-3-carbonitrile,
• (vi) 1-[4-chloro-3-(hydroxymethyl)benzyl]-4-(4-cyanophenyl)-2,5-dimethyl-1H-pyrrole-3-carbonitrile,
• (vii) 2-chloro-5-{[3-cyano-4-(4-cyanophenyl)-2,5-dimethyl-1H-pyrrol-1-yl]methyl}benzyl N,N-dimethylglycinate,
• (viii) 4-[(2-chloro-5-{[3-cyano-4-(4-cyanophenyl)-2,5-dimethyl-1H-pyrrol-1-yl]methyl}benzyl)oxy]-4-oxobutanoic acid,
• (ix) 4-[(2-chloro-5-{[3-cyano-4-(4-cyanophenyl)-5-methyl-2-propyl-1H-pyrrol-1-yl]methyl}pyridin-3-yl)methoxy]-4-oxobutanoic acid,
• (x) 4-[(2-chloro-5-{[3-cyano-4-(4-cyanophenyl)-2-ethyl-5-methyl-1H-pyrrol-1-yl]methyl}pyridin-3-yl)methoxy]-4-oxobutanoic acid,
• (xi) 4-[(2-chloro-5-{[3-cyano-4-(4-cyanophenyl)-2-cyclopropyl-5-methyl-1H-pyrrol-1-yl]methyl}pyridin-3-yl)methoxy]-4-oxobutanoic acid,
• (xii) 1-{[6-chloro-5-(2,2,2-trifluoro-1-hydroxyethyl)pyridin-3-yl]methyl}-4-(4-cyanophenyl)-2,5-dimethyl-1H-pyrrole-3-carbonitrile,
• (xiii) 4-(1-{[6-chloro-5-(hydroxymethyl)pyridin-3-yl]methyl}-2,5-dimethyl-1H-pyrrol-3-yl)benzonitrile,
• (xiv) 4-(1-{[6-chloro-5-(hydroxymethyl)pyridin-3-yl]methyl}-5-cyclopropyl-2-methyl-1H-pyrrol-3-yl)benzonitrile, or
• (xv) 1-{[6-chloro-5-(hydroxymethyl)pyridin-3-yl]methyl}-3-(4-cyanophenyl)-5-methyl-1H-pyrrole-2-carbonitrile, or a salt thereof.

A method for antagonizing an androgen receptor of a mammal which comprises administering an effective amount of a compound represented by the formula:

• wherein R1 represents a hydrogen atom, a cyano group or a group represented by the formula COORA (wherein RA represents an optionally substituted C1-6 alkyl group), R2 and R4 are the same or different, and each represents a hydrogen atom, a C1-6 alkyl group, a C3-6 cycloalkyl group, a trifluoromethyl group, an amino-C1-6 alkyl group, a mono- or di-substituted amino-C1-6 alkyl group, an optionally halogenated C1-6 alkyl group substituted with an optionally substituted hydroxyl group, a C2-6 alkenyl group substituted with an optionally substituted hydroxyl group, a C1-6 alkyl group substituted with an optionally substituted and optionally oxidized thiol group, an optionally substituted and optionally oxidized thiol group, a cyano group, an acyl group, an optionally substituted oxazolyl group or a 1,3-dioxolan-2-yl group, R3 represents a group represented by the formula:
• (wherein X represents a halogen atom, Y represents a carbon atom or a nitrogen atom, Alk represents an optionally substituted C1-4 alkylene group, and RB represents a hydrogen atom or an acyl group), and R5 represents a phenyl group which has a cyano group at a 4-position or a 3-position thereof and may be further substituted, or a salt or prodrug thereof to the mammal.

A method for preventing or treating hormone-sensitive cancer at an androgen dependent term and/or at an androgen independent term, which comprises administering an effective amount of a compound represented by the formula:

• wherein R1 represents a hydrogen atom, a cyano group or a group represented by the formula COORA (wherein RA represents an optionally substituted C1-6 alkyl group), R2 and R4 are the same or different, and each represents a hydrogen atom, a C1-6 alkyl group, a C3-6 cycloalkyl group, a trifluoromethyl group, an amino-C1-6 alkyl group, a mono- or di-substituted amino-C1-6 alkyl group, an optionally halogenated C1-6 alkyl group substituted with an optionally substituted hydroxyl group, a C2-6 alkenyl group substituted with an optionally substituted hydroxyl group, a C1-6 alkyl group substituted with an optionally substituted and optionally oxidized thiol group, an optionally substituted and optionally oxidized thiol group, a cyano group, an acyl group, an optionally substituted oxazolyl group or a 1,3-dioxolan-2-yl group, R3 represents a group represented by the formula:
• (wherein X represents a halogen atom, Y represents a carbon atom or a nitrogen atom, Alk represents an optionally substituted C1-4 alkylene group, and R3 represents a hydrogen atom or an acyl group), and R5 represents a phenyl group which has a cyano group at a 4-position or a 3-position thereof and may be further substituted, or a salt or prodrug thereof to a mammal.