4-oxoquinoline compound and use thereof as hiv integrase inhibitor

An anti-HIV agent comprising a compound of formula [I] or a solvate thereof or a stereoisomer thereof or a tautomer thereof or a pharmaceutically acceptable salt thereof as an active ingredient:

• 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 hydrogen atom, C1-4 alkyl group or benzyl group and Ra3 is C1-4 alkyl group;
• 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 atoms 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 a 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;
• 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;
• X is selected from a C—R32 or a nitrogen atom;
• and
• Y is selected from a C—R33 or a nitrogen atom
• wherein R32 and R33 are the same or different and each is selected from a hydrogen atom, cyano group, nitro group, halogen atom, 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 or, 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 selected from 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.

An anti-HIV agent comprising a compound of formula (III) or a solvate thereof or a stereoisomer thereof or a tautomer thereof or a pharmaceutically acceptable salt thereof as an active ingredient:

• 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, 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;
• 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.