Fused imidazolium derivatives

A 2-acylamino-3-amino-1,4-quinone derivative represented by the following general formula (II) or a salt thereof

• 116
• (wherein symbols in the formula have the following meanings;
• R1 and R2:
• the same or different from each other and each represents -(lower alkyl having one or more substituents selected from group B), -(lower alkenyl having one or more substituents selected from group B), -(lower alkynyl having one or more substituents selected from group B), -RinD, -lower alkyl, -lower alkenyl or -lower alkynyl, with the proviso that at least one of R1 and R2 is -(lower alkyl having one or more substituents selected from group B), -(lower alkenyl having one or more substituents selected from group B), -(lower alkynyl having one or more substituents selected from group B), -(cycloalkyl having one or more substituents) or -(five- to seven-membered saturated heterocyclic ring which may have one or more substituents),
• group B:
• —ORa, —SRa, -prodrug-formed OH, —O-lower alkylene-ORa, —O-lower alkylene-O-lower alkylene-ORa, —O-lower alkylene-NRaRb, —O-lower alkylene-O-lower alkylene-NRaRb, —O-lower alkylene-NRc-lower alkylene-NRaRb, —OCO—NRaRb, —SORa, —SO2Ra, —SO2NRaRb, —NRa—SO2Rb, —CO2H, —NRaRb, —NRc-lower alkylene-NRaRb, —N(-lower alkylene-NRaRb)2, -RinD, —NO2, —CN, -halogen, —CO2Ra, CO—NRaRb, —CONRa—O—Rb, —NRa—CORb, —NRa—CO—NRbRc, —OCORa and —CO—Ra,
• Ra, Rb and Rc:
• the same or different from one another and each represents —H, -lower alkyl, -lower alkylene-RinD or -RinD,
• RinD:
• -(five- to seven-membered saturated heterocyclic ring which may have one or more substituents), -(cycloalkyl which may have one or more substituents), -(cycloalkenyl which may have one or more substituents), -(aryl which may have one or more substituents) or -(heteroaryl which may have one or more substituents),
• R3:
• —H or -(lower alkyl which may have one or more substituents), or R2 and R3 may together form a lower alkylene having from 2 to 5 carbon atoms which may be interrupted with O, S or NR4 (R4:
• —H or -lower alkyl), and
• ring A:
• aryl ring which may have one or more substituents or heteroaryl ring which may have one or more substituents,
• with the proviso that compounds of the following table are excluded;
• 27 TABLE 1 (II-E) 117 Comp X R —R1 —R2 —R3 E-1 CH H —Me —CH2-(3,4-Cl—Ph) —Me E-2 CH H —CH(Me)2 —CH2-(3,4-Cl—Ph) —Me E-3 CH H —CH2—Ph -(4-MeO—Ph) —Me E-4 CH H —CH2—Ph -(3-Br—Ph) —Me E-5 CH H —CH2—Ph —CH2(4-F—Ph) —Me E-6 CH H —(CH2)2—Ph —CH2(4-F—Ph) —Me E-7 CH H —(CH2)2—OH —Me —Me E-8 CH H —(CH2)2—OH —CH2—Ph —Me E-9 CH H —(CH2)2—OH -(4-MeO—Ph) —Me E-10 CH H —(CH2)2—OH -(4-MeCO—Ph) —Me E-11 CH H —(CH2)2—OH -(3-Br—Ph) —Me E-12 CH H —(CH2)2—Cl —CH2CO2Et —Me E-13 CH H —CH(Me)—CO2H —Me —Me E-14 CH H —CH(Me)—CONHMe —Me —Me E-15 CH H —CH(Me)—CONHMe —CH(Me)2 —Me E-16 CH H —CH(Me)—CONHMe 118 —Me E-17 CH H —CH(Me)—CONHMe —Me —(CH2)2Me E-18 CH H —CH(Me)—CONHMe —Me —CH(Me)2 E-19 CH H —CH(Me)—CONHOMe —Me —Me E-20 N H —CH(Me)—CONHMe —Me —Me E-21 N Me —CH(Me)—CONHMe —Me —Me E-22 CH H 119 —Me —Me
• (in this table, Comp means compound number, Me means methyl group, Et means ethyl group and Ph means phenyl group, and in the case of a substituted phenyl group, the substituent is shown before Ph together with the substituting position, e.g., 3,4-Cl—Ph represents 3,4-dichlorophenyl).

A fused imidazole derivative represented by the following general formula (III) or a salt thereof

• 120
• (wherein symbols in the formula have the following meanings;
• R1:
• -(lower alkyl having one or more substituents selected from group B), -(lower alkenyl having one or more substituents selected from group B), -(lower alkynyl having one or more substituents selected from group B) or -(cycloalkyl having one or more substituents), with the proviso that a lower alkyl group having one or more substituents selected from the group consisting of —NH2, —NMe2, —NEt2, —OH, -halogen and -(phenyl which may be substituted by —Cl, —F, —Me or —OMe) is excluded,
• group B:
• ORa, —SRa, -prodrug-formed OH, —O-lower alkylene-ORa, —O-lower alkylene-O-lower alkylene-ORa, —O-lower alkylene-NRaRb, —O-lower alkylene-O-lower alkylene-NRaRb, —O-lower alkylene-NRc-lower alkylene-NRaRb, —OCO—NRaRb, —SORa, —SO2Ra, —SO2NRaRb, —NRa—SO2Rb, —CO2H, —NRaRb, —NRc-lower alkylene-NRaRb, —N(-lower alkylene-NRaRb)2, -RinD, —NO2, —CN, -halogen, —CO2Ra, —CONRaRb, —CONRa—O—Rb, —NRa—CORb, —NRa—CO—NRbRc, —OCORa and —CO—Ra,
• Ra, Rb and Rc:
• the same or different from one another and each represents —H, -lower alkyl, -lower alkylene-RinD or -RinD,
• RinD:
• -(five- to seven-membered saturated heterocyclic ring which may have one or more substituents), -(cycloalkyl which may have one or more substituents), -(cycloalkenyl which may have one or more substituents), -(aryl which may have one or more substituents) or -(heteroaryl which may have one or more substituents),
• R3:
• —H or -(lower alkyl which may have one or more substituents), and
• ring A:
• aryl ring which may have one or more substituents or heteroaryl ring which may have one or more substituents).