1-aryl-1,8-naphthylidin-4-one derivative as type IV phosphodiesterase inhibitor

A pharmaceutical composition comprising a 1-aryl-1,8-naphthylidin-4-one compound having the formula (I′):

• wherein R1 is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group,
• R2′, R3′, and R4′ independently are a hydrogen atom, or a substituted or unsubstituted lower alkyl group,
• X′ is a group NR5R6, wherein R1 and R6 independently are a hydrogen atom, a substituted or unsubstituted lower alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or a salt or solvate thereof.

A pharmaceutical composition comprising a 1-aryl-1,8-naphthylidin-4-one compound having the formula (I):

• wherein R1 is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group,
• R2, R3, and R4 independently are a hydrogen atom, a substituted or unsubstituted lower alkyl group,
• X is a group NR5R6, wherein R5 and R6 independently are a hydrogen atom, a substituted or unsubstituted lower alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

A method for inhibiting type IV phosphodiesterase comprising administering, to a patient in need thereof, an effective amount of a 1-aryl-1,8-naphthylidine-4-one compound having the formula (I):

• wherein R1 is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group,
• R2, R3, and R4 independently are a hydrogen atom, a substituted or unsubstituted lower alkyl group, or a halogen atom,
• X is a group NR5R6 or a group OR7, wherein R5 and R6 independently are a hydrogen atom, a substituted or unsubstituted lower alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and R7 is a hydrogen atom, a substituted or unsubstituted lower alkyl group, or a substituted or unsubstituted cycloalkyl group or a salt or solvate thereof.

A method for inhibiting production of TNF-α comprising administering, to a patient in need thereof, an effective amount of a 1-aryl-1,8-naphthylidine-4-one compound having the formula (I):

• wherein R1 is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group,
• R2, R3, and R4 independently are a hydrogen atom, a substituted or unsubstituted lower alkyl group, or a halogen atom,
• X is a group NR5,R6 or a group OR7, wherein R5 and R6 independently are a hydrogen atom, a substituted or unsubstituted lower alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and R7 is a hydrogen atom, a substituted or unsubstituted lower alkyl group, or a substituted or unsubstituted cycloalkyl group or a salt or solvate thereof.