Cyclic amine compound
A compound represented by the formula (I) wherein ring A is a 5- to 8-membered ring optionally having further substituent(s) other than R 6 , R 7 and R 8 , R 1 is an electron-withdrawing group, R 2 , R 3 , R 4 and R 5 are each independently a hydrogen atom, a halogen atom, a group bonded via a carbon atom, a group bonded via a nitrogen atom, a group bonded via an oxygen atom or a group bonded via a sulfur atom, R 6 is a halogen atom, a group bonded via a carbon atom, a group bonded via a nitrogen atom, a group bonded via an oxygen atom or a group bonded via a sulfur atom, R 7 is a cyano group, a nitro group, an acyl group optionally having substituent(s), an optionally esterified or amidated carboxyl group or a hydrocarbon group optionally having substituent(s), or R 6 and R 7 optionally form, together with the carbon atom bonded thereto, a ring optionally having substituent(s), and R 8 is a hydrogen atom, a halogen atom, a group bonded via a carbon atom, a group bonded via a nitrogen atom, a group bonded via an oxygen atom or a group bonded via a sulfur atom, or a salt thereof has a superior action as an androgen receptor modulator, and is useful for the prophylaxis or treatment of hypogonadism, male climacteric disorder, frailty, cachexia, osteoporosis and the like.
1. A compound represented by the formula (II)
wherein
ring A is a pyrrolidine ring or a piperidine ring,
R 1 is a cyano group,
R 2 is a hydrogen atom, a cyano group, a halogen atom, a C 1-6 alkyl group substituted with 1 to 5 halogen atoms, or a C 1-6 alkoxy group,
R 3 is a hydrogen atom, a cyano group, a halogen atom, a C 1-6 alkyl group substituted with 1 to 5 halogen atoms, a C 1-6 alkoxy group, a C 1-6 alkyl group, or a C 1-6 alkyl group substituted with hydroxy group(s),
R 4 is a hydrogen atom, a halogen atom, or a cyano group,
R 5 is a hydrogen atom, a halogen atom, or a C 1-6 alkyl group,
R 7 is a C 1-6 alkyl group,
R 8 is a hydrogen atom, and
X is a bond or a linker represented by CR 9 R 10 wherein R 9 is a C 1-6 alkyl group and R 10 is a C 1-6 alkyl group.
2. The compound of claim 1 , which is selected from
i) 2-chloro-4-[(2S,3S)-3-(1-hydroxy-1-methylethyl)-2-methylpyrrolidin-1-yl]-3-methylbenzonitrile,
ii) 2-chloro-4-[(2S,3S)-3-(1-hydroxy-1-methylethyl)-2-methylpyrrolidin-1-yl]benzonitrile,
iii) 4-[(2S,3S)-3-(1-hydroxy-1-methylethyl)-2-methylpyrrolidin-1-yl]-2-methoxybenzonitrile,
iv) 2-bromo-4-[(2S,3S)-3-(1-hydroxy-1-methylethyl)-2-methylpyrrolidin-1-yl]benzonitrile, and
v) 4-[(2S,3S)-3-hydroxy-2-methylpyrrolidin-1-yl]-3-(trifluoromethyl)benzonitrile.
3. A pharmaceutical agent comprising a compound of claim 1 or a salt thereof.
4. A method for the treatment of hypogonadism, male climacteric disorder, frailty, cachexia or osteoporosis in a mammal, which comprises administering an effective amount of a compound of claim 1 or a salt thereof.