1-phenyl-2-phenylethane derivative

A method for activating ERβ comprising administering to a subject in need thereof an effective amount of a compound of formula (1) or a salt thereof:

• wherein:
• R1 represents a cycloalkyl group having 3 to 8 carbon atoms, an alkenyl group having 2 to 6 carbon atoms and optionally substituted with a halogen atom, a 5-membered nitrogen-containing heteroaryl group, a 4- to 6-membered cyclic amino group, an alkanoylamino group having 2 to 6 carbon atoms and optionally substituted with a halogen atom, or a 1-trifluoromethyl-1-hydroxymethyl group;
• R2 to R5 are the same or different and each represent a hydrogen atom or a fluorine atom;
• and
• R6 represents a hydrogen atom or an alkanoyl group having 2 to 5 carbon atoms.

A method of preventing or ameliorating skin aging comprising administering to a subject in need thereof an effective amount of a compound of formula (1) or a salt thereof:

• wherein:
• R1 represents a cycloalkyl group having 3 to 8 carbon atoms, an alkenyl group having 2 to 6 carbon atoms and optionally substituted with a halogen atom, a 5-membered nitrogen-containing heteroaryl group, a 4- to 6-membered cyclic amino group, an alkanoylamino group having 2 to 6 carbon atoms and optionally substituted with a halogen atom, a 1-trifluoromethyl-1-hydroxymethyl group, or a 1-methylpropyl group;
• R2 to R5 are the same or different and each represent a hydrogen atom or a fluorine atom;
• and
• R6 represents a hydrogen atom or an alkanoyl group having 2 to 5 carbon atoms.

A method of inhibiting sebum secretion comprising administering to a subject in need thereof an effective amount of a compound of formula (1) or a salt thereof:

• wherein:
• R1 represents a cycloalkyl group having 3 to 8 carbon atoms, an alkenyl group having 2 to 6 carbon atoms and optionally substituted with a halogen atom, a 5-membered nitrogen-containing heteroaryl group, a 4- to 6-membered cyclic amino group, an alkanoylamino group having 2 to 6 carbon atoms and optionally substituted with a halogen atom, a 1-trifluoromethyl-1-hydroxymethyl group, or a 1-methylpropyl group;
• R2 to R5 are the same or different and each represent a hydrogen atom or a fluorine atom;
• and
• R6 represents a hydrogen atom or an alkanoyl group having 2 to 5 carbon atoms.

A method of ameliorating acne comprising administering to a subject in need thereof an effective amount of a compound of formula (1) or a salt thereof:

• wherein:
• R1 represents a cycloalkyl group having 3 to 8 carbon atoms, an alkenyl group having 2 to 6 carbon atoms and optionally substituted with a halogen atom, a 5-membered nitrogen-containing heteroaryl group, a 4- to 6-membered cyclic amino group, an alkanoylamino group having 2 to 6 carbon atoms and optionally substituted with a halogen atom, a 1-trifluoromethyl-1-hydroxymethyl group, or a 1-methylpropyl group;
• R2 to R5 are the same or different and each represent a hydrogen atom or a fluorine atom;
• and
• R6 represents a hydrogen atom or an alkanoyl group having 2 to 5 carbon atoms.

A method of ameliorating hot flash comprising administering to a subject in need thereof an effective amount of a compound of formula (1) or a salt thereof:

• wherein:
• R1 represents a cycloalkyl group having 3 to 8 carbon atoms, an alkenyl group having 2 to 6 carbon atoms and optionally substituted with a halogen atom, a 5-membered nitrogen-containing heteroaryl group, a 4- to 6-membered cyclic amino group, an alkanoylamino group having 2 to 6 carbon atoms and optionally substituted with a halogen atom, a 1-trifluoromethyl-1-hydroxymethyl group, or a 1-methylpropyl group;
• R2 to R5 are the same or different and each represent a hydrogen atom or a fluorine atom;
• and
• R6 represents a hydrogen atom or an alkanoyl group having 2 to 5 carbon atoms.

A method of ameliorating prostatic hyperplasia comprising administering to a subject in need thereof an effective amount of a compound of formula (1) or a salt thereof:

• wherein:
• R1 represents a cycloalkyl group having 3 to 8 carbon atoms, an alkenyl group having 2 to 6 carbon atoms and optionally substituted with a halogen atom, a 5-membered nitrogen-containing heteroaryl group, a 4- to 6-membered cyclic amino group, an alkanoylamino group having 2 to 6 carbon atoms and optionally substituted with a halogen atom, a 1-trifluoromethyl-1-hydroxymethyl group, or a 1-methylpropyl group;
• R2 to R5 are the same or different and each represent a hydrogen atom or a fluorine atom;
• and
• R6 represents a hydrogen atom or an alkanoyl group having 2 to 5 carbon atoms.

A method for inhibiting androgen activation comprising administering to a subject in need thereof an effective amount of a compound of formula (1) or a salt thereof:

• wherein:
• R1 represents a cycloalkyl group having 3 to 8 carbon atoms, an alkenyl group having 2 to 6 carbon atoms and optionally substituted with a halogen atom, a 5-membered nitrogen-containing heteroaryl group, a 4- to 6-membered cyclic amino group, an alkanoylamino group having 2 to 6 carbon atoms and optionally substituted with a halogen atom, a 1-trifluoromethyl-1-hydroxymethyl group, or a 1-methylpropyl group;
• R2 to R5 are the same or different and each represent a hydrogen atom or a fluorine atom;
• and
• R6 represents a hydrogen atom or an alkanoyl group having 2 to 5 carbon atoms.