Nitrogen-containing heteroaryl compounds having inhibitory activity against HIV integrase

1. A compound of the formula:

wherein

R B is hydrogen or a group selected from substitution group A (wherein the substitution group A is halogen, alkoxycarbonyl, carboxy, optionally substituted alkyl, alkoxy, alkoxyalkyl, nitro, hydroxy, optionally substituted alkenyl, alkynyl, alkylsulfonyl, optionally substituted amino, alkylthio, alkylthioalkyl, haloalkyl, haloalkoxy, haloalkoxyalkyl, cycloalkyl, cycloalkenyl, oxo, thioxo, alkylenedioxy, alkylene, alkenylene, nitroso, amidino, guanidino, cyano, isocyano, mercapto, optionally substituted carbamoyl, sulfamoyl, sulfoamino, formyl, alkylcarbonyl, alkylcarbonyloxy, hydrazino, morpholino, optionally substituted aralkyl, optionally substituted heteroaralkyl, optionally substituted aryloxy, optionally substituted heteroaryloxy, optionally substituted arylthio, optionally substituted heteroarylthio, optionally substituted aralkyloxy, optionally substituted heteroaralkyloxy, optionally substituted aralkylthio, optionally substituted heteroaralkylthio, optionally substituted aryloxyalkyl, optionally substituted heteroaryloxyalkyl, optionally substituted arylthioalkyl, optionally substituted heteroarylthioalkyl, optionally substituted arylsulfonyl, optionally substituted heteroarylsulfonyl, optionally substituted aralkylsulfonyl or optionally substituted heteroaralkylsulfonyl),

Z 6 is ═C(—R 5 ),

at least one of R 3 to R 5 is the formula: —Z 1 —Z 2 —Z 3 —R 1 (wherein Z 1 and Z 3 each is independently a bond, optionally substituted alkylene or optionally substituted alkenylene; Z 2 is a bond, optionally substituted alkylene, optionally substituted alkenylene, —CH(OH)—, —S—, —SO—, —SO 2 —, —SO 2 NR 2 —, —NR 2 SO 2 —, —O—, —NR 2 —, —NR 2 CO—, —CONR 2 —, —C(═O)—O—, —O—C(═O)— or —CO—; R 2 is hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted aryl or optionally substituted heteroaryl; and R 1 is optionally substituted aryl, optionally substituted heteroaryl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl or optionally substituted heterocycle), and the others of R 3 to R 5 are hydrogen or groups selected from the substitution group A, and

R 6 is hydrogen, or

a pharmaceutically acceptable salt thereof.

2. The compound according to claim 1 , wherein

R B is hydroxy, alkoxy or optionally substituted amino,

at least one of R 3 to R 5 is the formula: —Z 1 —Z 2 —Z 3 —R 1 (wherein Z 1 and Z 3 are bonds, Z 2 is a bond, alkylene or alkenylene, R 1 is optionally substituted aryl (the substituents are alkyl, halogen, alkoxy or haloalkyl)), and the others of R 3 to R 5 are aralkyl optionally substituted with halogen, hydrogen, halogen or alky, and

R 6 is hydrogen, or

a pharmaceutically acceptable salt thereof.

3. A compound of the formula:

wherein

R B is cycloalkyl or cycloalkenyl,

Z 6 is ═C(—R 5 ),

at least one of R 3 to R 5 and R 7 R 10 the formula: —Z 1 —Z 2 —Z 3 —R 1 (wherein Z 1 and Z 3 each is independently a bond, optionally substituted alkylene or optionally substituted alkenylene; Z 2 is a bond, optionally substituted alkylene, optionally substituted alkenylene, —CH(OH)—, —S—, —SO—, —SO 2 —, —SO 2 NR 2 —, —NR 2 SO 2 —, —O—, —NR 2 —, —NR 2 CO—, —CONR 2 —, —C(═O)—O—, or —CO—; R 2 is hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted aryl or optionally substituted heteroaryl; and R 1 is optionally substituted aryl, optionally substituted heteroaryl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl or optionally substituted heterocycle), and the others of R 3 to R 5 and R 7 to R 10 are hydrogen or groups selected from the substitution group A

(wherein the substitution group A is halogen, alkoxycarbonyl, carboxy, optionally substituted alkyl, alkoxy, alkoxyalkyl, nitro, hydroxy, optionally substituted alkenyl, alkynyl, alkylsulfonyl, optionally substituted amino, alkylthio, alkylthioalkyl, haloalkyl, haloalkoxy, haloalkoxyalkyl, cycloalkyl, cycloalkenyl, oxo, thioxo, alkylenedioxy, alkylene, alkenylene, nitroso, amidino, guanidino, cyano, isocyano, mercapto, optionally substituted carbamoyl, sulfamoyl, sulfoamino, formyl, alkylcarbonyl, alkylcarbonyloxy, hydrazino, morpholino, optionally substituted aralkyl, optionally substituted heteroaralkyl, optionally substituted aryloxy, optionally substituted heteroaryloxy, optionally substituted arylthio, optionally substituted heteroarylthio, optionally substituted aralkyloxy, optionally substituted heteroaralkyloxy, optionally substituted aralkylthio, optionally substituted heteroaralkylthio, optionally substituted aryloxyalkyl, optionally substituted heteroaryloxyalkyl, optionally substituted arylthioalkyl, optionally substituted heteroarylthioalkyl, optionally substituted arylsulfonyl, optionally substituted heteroarylsulfonyl, optionally substituted aralkylsulfonyl or optionally substituted heteroaralkylsulfonyl), and

R 6 is hydrogen, or

a pharmaceutically acceptable salt thereof.

4. The compound according to claim 3 , wherein

at least one of R 7 to R 5 and R 7 to R 10 is the formula: —Z 1 —Z 2 —Z 3 —R 1 (wherein Z 1 and Z 3 are bonds, Z 2 is alkylene, R 1 is optionally substituted aryl (the substituents are alkyl, halogen, alkoxy or haloalkyl)), and the others of R 3 to R 5 and R 7 to R 10 are hydrogen, alkyl or halogen, and

R 6 is hydrogen, or

a pharmaceutically acceptable salt thereof.

5. A pharmaceutical composition containing the compound according to claim 1 , or a pharmaceutically acceptable salt thereof, as the active ingredient together with a pharmaceutically acceptable carrier or dilluent.

6. An anti-HIV mixture which comprises a compound according to claim 1 , or a pharmaceutically acceptable salt thereof, in combination with a reverse transcriptase inhibitor and/or a protease inhibitor.

7. A pharmaceutical composition containing the compound according to claim 3 , or a pharmaceutically acceptable salt thereof, as the active ingredient together with a pharmaceutically acceptable carrier or dilluent.

8. An anti-HIV mixture which comprises a compound according to claim 3 , or a pharmaceutically acceptable salt thereof, in combination with a reverse transcriptase inhibitor and/or a protease inhibitor.