4-oxoquinoline compound and use thereof as pharmaceutical agent

A compound of formula [II] or a solvate thereof or a stereolsomer thereof or a tautomer thereof or a pharmaceutically acceptable salt thereof:

• wherein
• R4 and R6 are the same or different and each is a substituent selected from the following group A,
• wherein group A is a group consisting of cyano group, phenyl group, nitro group, halogen atom, C1-4 alkyl group, halo C1-4 alkyl group, halo C1-4 alkyloxy group, —ORa1, —SRa1, —NRa1Ra2, —CONRa1Ra2, —SO2NRa1Ra2, —CORa3, —NRa1CORa3, —SO2Ra3, —NRa1SO2Ra3, —COORa1, and —NRa2COORa3,
• wherein Ra1 and Ra2 are the same or different and each is selected from a hydrogen atom, C1-4 alkyl group, or benzyl group, and Ra3 is C1-4 alkyl group;
• R5 is a substituent selected from hydrogen atom and the above-mentioned group A, and R4 and R5 may form a fused ring together with a benzene ring they substitute;
• m is 0 or an integer of 1 to 3, and when m is 2 or 3, then R6 of each m may be the same or different;
• R1 is a substituent selected from the following group B or a C1-10 alkyl group optionally substituted by 1 to 3 substituents selected from halogen atom and the following group B,
• wherein group B is a group consisting of C3-10 carbon ring group optionally substituted by 1 to 5 substituents selected from the above-mentioned group A, heterocyclic group (wherein the heterocyclic group is a saturated or unsaturated ring containing, besides carbon atom(s), at least one heteroatom selected from a nitrogen atom, an oxygen atom, and a sulfur atom as defined above) optionally substituted by 1 to 5 substituents selected from the above-mentioned group A, —ORa4, —SRa4, —NRa4Ra5 —CONRa4Ra5, —SO2NRa4Ra5, —CORa6, —NRa4CORa6, —SO2Ra6, —NRa4SO2Ra6, —COORa4, and —NRa5COORa6,
• wherein Ra4 and Ra5 are the same or different and each is selected from a hydrogen atom, C1-4 alkyl group, C1-10 carbon ring group optionally substituted by 1 to 5 substituents selected from the above-mentioned group A, or heterocyclic group (as defined above) optionally substituted by 1 to 5 substituents selected from the above-mentioned group A, and Ra6 is selected from C1-4 alkyl group, C3-10 carbon ring group optionally substituted by 1 to 5 substituents selected from the above-mentioned group A, or heterocyclic group (as defined above) optionally substituted by 1 to 5 substituents selected from the above-mentioned group A;
• R31 is selected from a hydrogen atom, a cyano group, a hydroxy group, an amino group, a nitro group, a halogen atom, a C1-4 alkyl group, a C1-4 alkoxy group, a C1-4 alkylsulfanyl group, a halo C1-4 alkyl group, or a halo C1-4 alkyloxy group;
• and
• R32 and R33 are the same or different and each is selected from
• a hydrogen atom,
• a cyano group,
• a nitro group,
• a halogen atom,
• a C3-10 carbon ring group optionally substituted by 1 to 5 substituents selected from the above-mentioned group A,
• a heterocyclic group (as defined above) optionally substituted by 1 to 5 substituents selected from the above-mentioned group A, C1-10 alkyl group optionally substituted by 1 to 3 substituents selected from halogen atom and the above-mentioned group B, ORa7, —SRa7, —NRa7Ra8, —NRa7CORa9, —COORa10, or —N═CH—NRa10Ra11,
• wherein Ra7 and Ra8 are the same or different and each is selected from a hydrogen atom, group B or C1-10 alkyl group optionally substituted by 1 to 3 substituents selected from halogen atom and the above-mentioned group B, Ra9 is C1-4 alkyl group, and Ra10 and Ra11 are the same or different and each is selected from a hydrogen atom or C1-4 alkyl group.

A method for the treatment of an HIV infection, comprising:

• administering to a mammal in need thereof a therapeutically effective amount of a compound of formula (III) or a solvate thereof or a stereoisomer thereof or a tautomer thereof or a pharmaceutically acceptable salt thereof:
• wherein
• ring Cy is a C3-10 carbon ring group optionally substituted by 1 to 5 substituents selected from the following group A or a heterocyclic group optionally substituted by 1 to 5 substituents selected from the following group A,
• wherein the heterocyclic group is a saturated or unsaturated ring containing, besides carbon atom(s), at least one heteroatom selected from a nitrogen atom, an oxygen atom and a sulfur atom, group A is a group consisting of cyano group, phenyl group, nitro group, halogen atom, C1-4 alkyl group, halo C1-4 alkyl group, halo C1-4 alkyloxy group, —ORa1, —SRa1, —NRa1Ra2, —CONRa1Ra2, —SO2NRa1Ra2, —CORa3, —NRa1CORa3, —SO2Ra3, —NRa1SO2Ra3, —COORa1, and —NRa2COORa3,
• wherein Ra1 and Ra2 are the same or different and each is selected from a hydrogen atom or C1-4 alkyl group, and Ra3 is C1-4 alkyl group;
• R1 is a substituent selected from the following group B or a C1-6 alkyl group optionally substituted by 1 to 3 substituents selected from halogen atom and the following group B,
• wherein group B is a group consisting of C3-10 carbon ring group optionally substituted by 1 to 5 substituents selected from the above-mentioned group A, heterocyclic group (as defined above) optionally substituted by 1 to 5 substituents selected from the above-mentioned group A, —ORa4, —SRa4, —NRa4Ra5, —CONRa4Ra5, —SO2NRa4Ra5, —CORa6, —NRa4CORa6, —SO2Ra6, —NRa4SO2Ra6, —COORa4, and —NRa5COORa6,
• wherein Ra4 and Ra5 are the same or different and each is selected from a hydrogen atom, C1-4 alkyl group, C3-10 carbon ring group optionally substituted by 1 to 5 substituents selected from the above-mentioned group A, or heterocyclic group (as defined above) optionally substituted by 1 to 5 substituents selected from the above-mentioned group A, and Ra6 is selected from C1-4 alkyl group, C3-10 carbon ring group optionally substituted by 1 to 5 substituents selected from the above-mentioned group A, or heterocyclic group (as defined above) optionally substituted by 1 to 5 substituents selected from the above-mentioned group A;
• R2 is selected from a hydrogen atom or a C1-4 alkyl group;
• R3 is selected from a cyano group, a hydroxy group, an amino group, a nitro group, a halogen atom, a C1-4 alkyl group, a C1-4 alkoxy group, a C1-4 alkylsulfanyl group, a halo C1-4 alkyl group, or a halo C1-4 alkyloxy group;
• n is selected from 0 or an integer of 1 to 3 and when n is 2 or 3, R3 each may be the same or different.