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Claims for Patent: 7,176,220

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Claims for Patent: 7,176,220

Title:4-oxoquinoline compound and use thereof as pharmaceutical agent
Abstract: An anti-HIV agent containing, as an active ingredient, a 4-oxoquinoline compound represented by the following formula [I] ##STR00001## wherein each symbol is as defined in the specification, or a pharmaceutically acceptable salt thereof. The compound of the present invention has HIV integrase inhibitory action and is useful as an anti-HIV agent for the prophylaxis or therapy of AIDS. Moreover, by a combined use with other anti-HIV agents such as protease inhibitors, reverse transcriptase inhibitors and the like, the compound can become a more effective anti-HIV agent. Since the compound has high inhibitory activity specific for integrases, it can provide a safe pharmaceutical agent with a fewer side effects for human.
Inventor(s): Satoh; Motohide (Takatsuki, JP), Kawakami; Hiroshi (Takatsuki, JP), Itoh; Yoshiharu (Takatsuki, JP), Shinkai; Hisashi (Takatsuki, JP), Motomura; Takahisa (Takatsuki, JP), Aramaki; Hisateru (Takatsuki, JP), Matsuzaki; Yuji (Takatsuki, JP), Watanabe; Wataru (Takatsuki, JP), Wamaki; Shuichi (Takatsuki, JP)
Assignee: Japan Tobacco Inc. (Tokyo, JP)
Application Number:10/492,833
Patent Claims: 1. 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 [I], or a solvate thereof or a stereoisomer thereof or a tautomer thereof or a pharmaceutically acceptable salt thereof: ##STR00346## wherein, ring Cy is a C.sub.3-10 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, C.sub.1-4 alkyl group, halo C.sub.1-4 alkyl group, halo C.sub.1-4 alkyloxy group, --OR.sup.a1, --SR.sup.a1, --NR.sup.a1R.sup.a2, --CONR.sup.a1R.sup.a2, --SO.sub.2NR.sup.a1R.sup.a2, --COR.sup.a3, --NR.sup.a1COR.sup.a3, --SO.sub.2R.sup.a3, --NR.sup.a1SO.sub.2R.sup.a3, --COOR.sup.a1, and --NR.sup.a2COOR.sup.a3, wherein R.sup.a1 and R.sup.a2 are the same or different and each is hydrogen atom, C.sub.1-4 alkyl group or benzyl group and R.sup.a3 is C.sub.1-4 alkyl group; R.sup.1 is a substituent selected from the following group B or a C.sub.1-10 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 C.sub.3-10 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.sup.a4, --SR.sup.a4, --NR.sup.a4R.sup.a5, --CONR.sup.a4R.sup.a5, --SO.sub.2NR.sup.a4R.sup.a5, --COR.sup.a6, --NR.sup.a4COR.sup.a6, --SO.sub.2R.sup.a6, --NR.sup.a4SO.sub.2R.sup.a6, --COOR.sup.a4, and --NR.sup.a5COOR.sup.a6, wherein R.sup.a4 and R.sup.a5 are the same or different and each is selected from a hydrogen atom, C.sub.1-4 alkyl group, C.sub.3-10 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 R.sup.a6 is selected from a C.sub.1-4 alkyl group, C.sub.3-10 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; R.sup.2 is selected from a hydrogen atom or a C.sub.1-4 alkyl group; R.sup.31 is selected from a hydrogen atom, a cyano group, a hydroxy group, an amino group, a nitro group, a halogen atom, a C.sub.1-4 alkyl group, a C.sub.1-4 alkoxy group, a C.sub.1-4 alkylsulfanyl group, a halo C.sub.1-4 alkyl group, or a halo C.sub.1-4 alkyloxy group; X is selected from a C--R.sup.32 or a nitrogen atom; and Y is selected from a C--R.sup.33 or a nitrogen atom, wherein R.sup.32 and R.sup.33 are the same or different and each is selected from a hydrogen atom, cyano group, nitro group, halogen atom, C.sub.3-10 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, C.sub.1-10 alkyl group optionally substituted by 1 to 3 substituents selected from halogen atom and the above-mentioned group B, --OR.sup.a7, --SR.sup.a7, --NR.sup.a7R.sup.a8, --NR.sup.a7COR.sup.a9, --COOR.sup.a10, or --N.dbd.CH--NR.sup.a10R.sup.a11, wherein R.sup.a7 and R.sup.a8 are the same or different and each is selected from a hydrogen atom, group B, or C.sub.1-10 alkyl group optionally substituted by 1 to 3 substituents selected from halogen atom and the above-mentioned group B, R.sup.a9 is selected from C.sub.1-4 alkyl group, and R.sup.a10 and R.sup.a11 are the same or different and each is selected from a hydrogen atom or C.sub.1-4 alkyl group.

2. The method of claim 1, wherein X is C--R.sup.32 and Y is C--R.sup.33.

3. The method of claim 1, wherein ring Cy is ##STR00347## wherein R.sup.4 and R.sup.6 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, C.sub.1-4 alkyl group, halo C.sub.1-4 alkyl group, halo C.sub.1-4 alkyloxy group, --OR.sup.a1, --NR.sup.a1, --NR.sup.a1R.sup.a2, --CONR.sup.a1R.sup.a2, --SO.sub.2NR.sup.a1R.sup.a2, --COR.sup.a3, --NR.sup.a1COR.sup.a3, --SO.sub.2R.sup.a3, --NR.sup.a1SO.sub.2R.sup.a3, --COOR.sup.a1, and --NR.sup.a2COOR.sup.a3, wherein R.sup.a1 and R.sup.a2 are the same or different and each is selected from a hydrogen atom, C.sub.1-4 alkyl group, or benzyl group, and R.sup.a3 is C.sub.1-4 alkyl group; R.sup.5 is a substituent selected from hydrogen atom and group A, and R.sup.4 and R.sup.5 may form a fused ring together with a benzene ring they substitute; and m is 0 or an integer of 1 to 3, and when m is 2 or 3, then R.sup.6 of each m may be the same or different.

4. The method of claim 1, wherein R.sup.2 is a hydrogen atom.

5. A compound of formula [II] or a solvate thereof or a stereolsomer thereof or a tautomer thereof or a pharmaceutically acceptable salt thereof: ##STR00348## wherein R.sup.4 and R.sup.6 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, C.sub.1-4 alkyl group, halo C.sub.1-4 alkyl group, halo C.sub.1-4 alkyloxy group, --OR.sup.a1, --SR.sup.a1, --NR.sup.a1R.sup.a2, --CONR.sup.a1R.sup.a2, --SO.sub.2NR.sup.a1R.sup.a2, --COR.sup.a3, --NR.sup.a1COR.sup.a3, --SO.sub.2R.sup.a3, --NR.sup.a1SO.sub.2R.sup.a3, --COOR.sup.a1, and --NR.sup.a2COOR.sup.a3, wherein R.sup.a1 and R.sup.a2 are the same or different and each is selected from a hydrogen atom, C.sub.1-4 alkyl group, or benzyl group, and R.sup.a3 is C.sub.1-4 alkyl group; R.sup.5 is a substituent selected from hydrogen atom and the above-mentioned group A, and R.sup.4 and R.sup.5 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 R.sup.6 of each m may be the same or different; R.sup.1 is a substituent selected from the following group B or a C.sub.1-10 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 C.sub.3-10 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, --OR.sup.a4, --SR.sup.a4, --NR.sup.a4R.sup.a5 --CONR.sup.a4R.sup.a5, --SO.sub.2NR.sup.a4R.sup.a5, --COR.sup.a6, --NR.sup.a4COR.sup.a6, --SO.sub.2R.sup.a6, --NR.sup.a4SO.sub.2R.sup.a6, --COOR.sup.a4, and --NR.sup.a5COOR.sup.a6, wherein R.sup.a4 and R.sup.a5 are the same or different and each is selected from a hydrogen atom, C.sub.1-4 alkyl group, C.sub.1-10 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 R.sup.a6 is selected from C.sub.1-4 alkyl group, C.sub.3-10 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; R.sup.31 is selected from a hydrogen atom, a cyano group, a hydroxy group, an amino group, a nitro group, a halogen atom, a C.sub.1-4 alkyl group, a C.sub.1-4 alkoxy group, a C.sub.1-4 alkylsulfanyl group, a halo C.sub.1-4 alkyl group, or a halo C.sub.1-4 alkyloxy group; and R.sup.32 and R.sup.33 are the same or different and each is selected from a hydrogen atom, a cyano group, a nitro group, a halogen atom, a C.sub.3-10 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, C.sub.1-10 alkyl group optionally substituted by 1 to 3 substituents selected from halogen atom and the above-mentioned group B, OR.sup.a7, --SR.sup.a7, --NR.sup.a7R.sup.a8, --NR.sup.a7COR.sup.a9, --COOR.sup.a10, or --N.dbd.CH--NR.sup.a10R.sup.a11, wherein R.sup.a7 and R.sup.a8 are the same or different and each is selected from a hydrogen atom, group B or C.sub.1-10 alkyl group optionally substituted by 1 to 3 substituents selected from halogen atom and the above-mentioned group B, R.sup.a9 is C.sub.1-4 alkyl group, and R.sup.a10 and R.sup.a11 are the same or different and each is selected from a hydrogen atom or C.sub.1-4 alkyl group.

6. The compound of claim 5, wherein R.sup.31 is selected from a hydrogen atom, a cyano group, a hydroxy group, or a C.sub.1-4 alkoxy group, or a solvate thereof or a stereoisomer thereof or a tautomer thereof or a pharmaceutically acceptable salt thereof.

7. The compound of claim 6, wherein R.sup.31 is selected from a hydrogen atom, or a solvate thereof or a stereoisomer thereof or a tautomer thereof or a pharmaceutically acceptable salt thereof.

8. The compound of claim 5, wherein R.sup.32 and R.sup.33 are the same or different and each is selected from a hydrogen atom, a cyano group, a halogen atom, 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, and group A is a group consisting of cyano group, phenyl group, nitro group, halogen atom, C.sub.1-4 alkyl group, halo C.sub.1-4 alkyl group, halo C.sub.1-4 alkyloxy group, --OR.sup.a1, --SR.sup.a1, --NR.sup.a1R.sup.a2, --CONR.sup.a1R.sup.a2, --SO.sub.2NR.sup.a1R.sup.a2, --COR.sup.a3, --NR.sup.a1COR.sup.a3, --SO.sub.2R.sup.a3, --NR.sup.a1SO.sub.2R.sup.a3, --COOR.sup.a1, and --NR.sup.a2COOR.sup.a3, wherein R.sup.a1 and R.sup.a2 are the same or different and each is hydrogen atom, C.sub.1-4 alkyl group, or benzyl group, and R.sup.a3 is C.sub.1-4 alkyl group, a C.sub.1-10 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 C.sub.3-10 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.sup.a4, --SR.sup.a4, --NR.sup.a4R.sup.a5, --CONR.sup.a4R.sup.a5, --SO.sub.2NR.sup.a4R.sup.a5, --COR.sup.a6, --NR.sup.a4COR.sup.a6, --SO.sub.2R.sup.a6, --NR.sup.a4SO.sub.2R.sup.a6, --COOR.sup.a4, and --NR.sup.a5COOR.sup.a6, wherein R.sup.a4 and R.sup.a5 are the same or different and each is selected from a hydrogen atom, C.sub.1-4 alkyl group, C.sub.3-10 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 R.sup.a6 is selected from C.sub.1-4 alkyl group, C.sub.3-10 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, --OR.sup.a7, --SR.sup.a7, --NR.sup.a7R.sup.a8, --NR.sup.a7COR.sup.a9, --COOR.sup.a10, or --N.dbd.CH--NR.sup.a10R.sup.a11, wherein R.sup.a7 and R.sup.a8 are the same or different and each is selected from a hydrogen atom, group B, or C.sub.1-10 alkyl group optionally substituted by 1 to 3 substituents selected from halogen atom and the above-mentioned group B, R.sup.a9 is C.sub.1-4 alkyl group, and R.sup.a10 and R.sup.a11 are the same or different and each is selected from a hydrogen atom or C.sub.1-4 alkyl group, or a solvate thereof or a stereolsomer thereof or a tautomer thereof or a pharmaceutically acceptable salt thereof.

9. The compound of claim 5, wherein R.sup.32 is selected from a hydrogen atom, a cyano group, a halogen atom, a C.sub.1-10 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 C.sub.3-10 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) optionally substituted by 1 to 5 substituents selected from the above-mentioned group A, --OR.sup.a4, --SR.sup.a4, --NR.sup.a4R.sup.a5, --CONR.sup.a4R.sup.a5, --SO.sub.2NR.sup.a4R.sup.a5, --COR.sup.a6, --NR.sup.a4COR.sup.a6, --SO.sub.2R.sup.a6, --NR.sup.a4SO.sub.2R.sup.a6, --COOR.sup.a4, and --NR.sup.a5COOR.sup.a6, wherein R.sup.a4 and R.sup.a5 are the same or different and each is selected from a hydrogen atom, C.sub.1-4 alkyl group, C.sub.3-10 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 R.sup.a6 is selected from C.sub.1-4 alkyl group, C.sub.3-10 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, --OR.sup.a7, --SR.sup.a7, --NR.sup.a7R.sup.a8, --NR.sup.a7COR.sup.a9, or --COOR.sup.a10, wherein R.sup.a7 and R.sup.a8 are the same or different and each is selected from a hydrogen atom, group B, or C.sub.1-10 alkyl group optionally substituted by 1 to 3 substituents selected from halogen atom and the above-mentioned group B, R.sup.a9 is C.sub.1-4 alkyl group, and R.sup.a10 is selected from a hydrogen atom or C.sub.1-4 alkyl group, or a solvate thereof or a stereoisomer thereof or a tautomer thereof or a pharmaceutically acceptable salt thereof.

10. The compound of claim 9, wherein R.sup.32 is selected from a hydrogen atom, --OR.sup.a7, or --NR.sup.a7R.sup.a8, wherein R.sup.a7 and R.sup.a8 are the same or different and each is selected from a hydrogen atom, group B, or C.sub.1-10 alkyl group optionally substituted by 1 to 3 substituents selected from halogen atom and the above-mentioned group B, or a solvate thereof or a stereoisomer thereof or a tautomer thereof or a pharmaceutically acceptable salt thereof.

11. The compound of claim 8, wherein R.sup.33 is selected from a hydrogen atom, a C.sub.1-10 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 C.sub.3-10 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) optionally substituted by 1 to 5 substituents selected from the above-mentioned group A, --OR.sup.a4, --SR.sup.a4, --NR.sup.a4R.sup.a5, --CONR.sup.a4R.sup.a5, --SO.sub.2NR.sup.a4R.sup.a5, --COR.sup.a6, --NR.sup.a4COR.sup.a6, --SO.sub.2R.sup.a6, --NR.sup.a4SO.sub.2R.sup.a6, --COOR.sup.a4, and --NR.sup.a5COOR.sup.a6, wherein R.sup.a4 and R.sup.a5 are the same or different and each is selected from a hydrogen atom, C.sub.1-4 alkyl group, C.sub.3-10 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 R.sup.a6 is selected from C.sub.1-4 alkyl group, C.sub.3-10 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, --OR.sup.a7, or --NR.sup.a7R.sup.a8 wherein R.sup.a7 and R.sup.a8 are the same or different and each is selected from a hydrogen atom, group B, or C.sub.1-10 alkyl group, optionally substituted by 1 to 3 substituents selected from halogen atom and the above-mentioned group B, or a solvate thereof or a stereoisomer thereof or a tautomer thereof or a pharmaceutically acceptable salt thereof.

12. The compound of claim 11, wherein R.sup.33 is selected from a hydrogen atom, --OR.sup.a7, or --NR.sup.a7R.sup.a8, wherein R.sup.a7 and R.sup.a8 are the same or different and each is selected from a hydrogen atom, group B or C.sub.1-10 alkyl group optionally substituted by 1 to 3 substituents selected from halogen atom and the above-mentioned group B, or a solvate thereof or a stereolsomer thereof or a tautomer thereof or a pharmaceutically acceptable salt thereof.

13. The compound of claim 5, wherein R.sup.a7 and R.sup.a8 are the same or different and each is selected from a C.sub.1-10 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 C.sub.3-10 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) optionally substituted by 1 to 5 substituents selected from the above-mentioned group A, --OR.sup.a4, --SR.sup.a4, --NR.sup.a4R.sup.a5, --CONR.sup.a4R.sup.a5, --SO.sub.2NR.sup.a4R.sup.a5, --COR.sup.a6, --NR.sup.a4COR.sup.a6, --SO.sub.2R.sup.a6, --NR.sup.a4SO.sub.2R.sup.a6, --COOR.sup.a4, and --NR.sup.a5COOR.sup.a6, wherein R.sup.a4 and R.sup.a5 are the same or different and each is selected from a hydrogen atom, C.sub.1-4 alkyl group, C.sub.3-10 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 R.sup.a6 is selected from C.sub.1-4 alkyl group, C.sub.3-10 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, or a solvate thereof or a stereoisomer thereof or a tautomer thereof or a pharmaceutically acceptable salt thereof.

14. The compound of claim 5, wherein R.sup.4 and R.sup.5 are the same or different and each is a substituent selected from cyano group, phenyl group, nitro group, halogen atom, C.sub.1-4 alkyl group, halo C.sub.1-4 alkyl group, halo C.sub.1-4 alkyloxy group, --OR.sup.a1, --SR.sup.a1, --NR.sup.a1R.sup.a2, --CONR.sup.a1R.sup.a2, --SO.sub.2NR.sup.a1R.sup.a2, --NR.sup.a1COR.sup.a3, --SO.sub.2R.sup.a3, --NR.sup.a2COOR.sup.a3, and --COOR.sup.a1, wherein R.sup.a1 and R.sup.a2 are the same or different and each is hydrogen atom, C.sub.1-4 alkyl group, or benzyl group, and R.sup.a3 is C.sub.1-4 alkyl group, or a solvate thereof or a stereoisomer thereof or a tautomer thereof or a pharmaceutically acceptable salt thereof.

15. The compound of claim 14, wherein R.sup.4 is selected from a phenyl group, a halogen atom, a C.sub.1-4 alkyl group, a halo C.sub.1-4 alkyloxy group, --OR.sup.a1, --NR.sup.a1R.sup.a2, --CONR.sup.a1R.sup.a2, --SO.sub.2NR.sup.a1R.sup.a2, --NR.sup.a1COR.sup.a3, --SO.sub.2R.sup.a3, --NR.sup.a1SO.sub.2R.sup.a3, or --COOR.sup.a1, wherein R.sup.a1 and R.sup.a2 are the same or different and each is selected from a hydrogen atom, C.sub.1-4 alkyl group or benzyl group, and R.sup.a3 is C.sub.1-4 alkyl group, or a solvate thereof or a stereoisomer thereof or a tautomer thereof or a pharmaceutically acceptable salt thereof.

16. The compound of claim 15, wherein R.sup.4 is a halogen atom, or a solvate thereof or a stereolsomer thereof or a tautomer thereof or a pharmaceutically acceptable salt thereof.

17. The compound of claim 5, wherein R.sup.5 is selected from a hydrogen atom, a cyano group, a phenyl group, a nitro group, a halogen atom, a C.sub.1-4 alkyl group, a halo C.sub.1-4 alkyl group, --OR.sup.a1, --SR.sup.a1, --NR.sup.a1R.sup.a2, --CONR.sup.a1R.sup.a2, --SO.sub.2NR.sup.a1R.sup.a2, or --NR.sup.a1COR.sup.a3, wherein R.sup.a1 and R.sup.a2 are the same or different and each is selected from a hydrogen atom, C.sub.1-4 alkyl group, or benzyl group, and R.sup.a3 is C.sub.1-4 alkyl group, or a solvate thereof or a stereoisomer thereof or a tautomer thereof or a pharmaceutically acceptable salt thereof.

18. The compound of claim 5, wherein R.sup.6 is a halogen atom, or a solvate thereof or a stereoisomer thereof or a tautomer thereof or a pharmaceutically acceptable salt thereof.

19. The compound of claim 5, wherein m is 0 or 1, or a solvate thereof or a stereoisomer thereof or a tautomer thereof or a pharmaceutically acceptable salt thereof.

20. The compound of claim 5, wherein R.sup.1 is selected from a C.sub.3-10 carbon ring group optionally substituted by 1 to 5 substituents selected from the following group A, wherein group A is a group consisting of cyano group, phenyl group, nitro group, halogen atom, C.sub.1-4 alkyl group, halo C.sub.1-4 alkyl group, halo C.sub.1-4 alkyloxy group, --OR.sup.a1, --SR.sup.a1, --NR.sup.a1R.sup.a2, --CONR.sup.a1R.sup.a2, --SO.sub.2NR.sup.a1R.sup.a2, --COR.sup.a3, --NR.sup.a1COR.sup.a3, --SO.sub.2R.sup.a3, --NR.sup.a1SO.sub.2R.sup.a3, --COOR.sup.a1, and --NR.sup.a2COOR.sup.a3, wherein R.sup.a1 and R.sup.a2 are the same or different and each is selected from a hydrogen atom, C.sub.1-4 alkyl group, or benzyl group, and R.sup.a3 is C.sub.1-4 alkyl group, a substituent selected from --NR.sup.a4R.sup.a5, --NR.sup.a4COR.sup.a6, --NR.sup.a4SO.sub.2R.sup.a6, and --NR.sup.a5COOR.sup.a6, wherein R.sup.a4 and R.sup.a5 are the same or different and each is selected from a hydrogen atom, C.sub.1-4 alkyl group, C.sub.3-10 carbon ring group optionally substituted by 1 to 5 substituents selected from the above-mentioned group A, or 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) optionally substituted by 1 to 5 substituents selected from the above-mentioned group A, and R.sup.a6 is selected from C.sub.1-4 alkyl group, C.sub.3-10 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, or a C.sub.1-10 alkyl group optionally substituted by 1 to 3 substituents selected from halogen atom and group B, wherein group B is a group consisting of C.sub.3-10 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.sup.a4, --SR.sup.a4, --NR.sup.a4R.sup.a5, --CONR.sup.a4R.sup.a5, --SO.sub.2NR.sup.a4R.sup.a5, --COR.sup.a6, --NR.sup.a4COR.sup.a6, --SO.sub.2R.sup.a6, --NR.sup.a4SO.sub.2R.sup.a6, --COOR.sup.a4, and --NR.sup.a5COOR.sup.a6 (wherein R.sup.a4, R.sup.a5, R.sup.a6, and group A are as defined above), or a solvate thereof or a stereoisomer thereof or a tautomer thereof or a pharmaceutically acceptable salt thereof.

21. The compound of claim 20, wherein R.sup.1 is a C.sub.1-10 alkyl group optionally substituted by 1 to 3 substituents selected from halogen atom and group B, wherein group B is a group consisting of C.sub.3-10 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.sup.a4, --SR.sup.a4, --NR.sup.a4R.sup.a5, --CONR.sup.a4R.sup.a5, --SO.sub.2NR.sup.a4R.sup.a5, --COR.sup.a6, --NR.sup.a4COR.sup.a6, --SO.sub.2R.sup.a6, --NR.sup.a4SO.sub.2R.sup.a6, --COOR.sup.a4, and --NR.sup.a5COOR.sup.a6, wherein R.sup.a4 and R.sup.a5 are the same or different and each is selected from a hydrogen atom, C.sub.1-4 alkyl group, C.sub.3-10 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 R.sup.a6 is selected from C.sub.1-4 alkyl group, C.sub.3-10 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, or a solvate thereof or a stereoisomer thereof or a tautomer thereof or a pharmaceutically acceptable salt thereof.

22. 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: ##STR00349## wherein ring Cy is a C.sub.3-10 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, C.sub.1-4 alkyl group, halo C.sub.1-4 alkyl group, halo C.sub.1-4 alkyloxy group, --OR.sup.a1, --SR.sup.a1, --NR.sup.a1R.sup.a2, --CONR.sup.a1R.sup.a2, --SO.sub.2NR.sup.a1R.sup.a2, --COR.sup.a3, --NR.sup.a1COR.sup.a3, --SO.sub.2R.sup.a3, --NR.sup.a1SO.sub.2R.sup.a3, --COOR.sup.a1, and --NR.sup.a2COOR.sup.a3, wherein R.sup.a1 and R.sup.a2 are the same or different and each is selected from a hydrogen atom or C.sub.1-4 alkyl group, and R.sup.a3 is C.sub.1-4 alkyl group; R.sup.1 is a substituent selected from the following group B or a C.sub.1-6 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 C.sub.3-10 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.sup.a4, --SR.sup.a4, --NR.sup.a4R.sup.a5, --CONR.sup.a4R.sup.a5, --SO.sub.2NR.sup.a4R.sup.a5, --COR.sup.a6, --NR.sup.a4COR.sup.a6, --SO.sub.2R.sup.a6, --NR.sup.a4SO.sub.2R.sup.a6, --COOR.sup.a4, and --NR.sup.a5COOR.sup.a6, wherein R.sup.a4 and R.sup.a5 are the same or different and each is selected from a hydrogen atom, C.sub.1-4 alkyl group, C.sub.3-10 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 R.sup.a6 is selected from C.sub.1-4 alkyl group, C.sub.3-10 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; R.sup.2 is selected from a hydrogen atom or a C.sub.1-4 alkyl group; R.sup.3 is selected from a cyano group, a hydroxy group, an amino group, a nitro group, a halogen atom, a C.sub.1-4 alkyl group, a C.sub.1-4 alkoxy group, a C.sub.1-4 alkylsulfanyl group, a halo C.sub.1-4 alkyl group, or a halo C.sub.1-4 alkyloxy group; n is selected from 0 or an integer of 1 to 3 and when n is 2 or 3, R.sup.3 each may be the same or different.

23. A pharmaceutical composition comprising a compound according to claim 5, or a solvate thereof or a stereoisomer thereof or a tautomer thereof or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.

24. A method for the treatment of an HIV infection, which comprises administering to a mammal in need thereof a therapeutically effective amount of a compound according to claim 5, or a solvate thereof or a stereoisomer thereof or a tautomer thereof or a pharmaceutically acceptable salt thereof.

25. The method according to claim 24, wherein the compound is administered at a dosage ranging from 0.01 mg to 1 g per administration for an adult.

26. The method according to claim 24, wherein the compound is administered at a dosage for inhibiting activity specific for HIV integrase.

27. A method for inhibiting HIV integrase, comprising administering to a mammal in need thereof an HIV integrase inhibiting effective amount of a compound according to claim 5 or a solvate thereof or a stereoisomer thereof or a tautomer thereof or a pharmaceutically acceptable salt thereof.

28. A method for the treatment of an HIV infection, comprising: administering to a mammal in need thereof a composition comprising a therapeutically effective amount of a compound of the formula: ##STR00350## or a solvate thereof or a tautomer thereof or a pharmaceutically acceptable salt thereof.

29. A method for inhibiting HIV integrase, comprising: administering to a mammal in need thereof a composition comprising an HIV integrase inhibiting effective amount of a compound of the formula: ##STR00351## or a solvate thereof or a tautomer thereof or a pharmaceutically acceptable salt thereof.

30. A compound of the formula: ##STR00352## or a solvate thereof or a tautomer thereof or a pharmaceutically acceptable salt thereof.

31. The method according to any one of claims 1, 22, 24, 27, 28 or 29 wherein the mammal is a human.
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