Pyridone derivative having integrase inhibitory activity

A compound represented by the formula:

• wherein
• R4 is hydrogen, optionally substituted lower alkyl (with the proviso that the substituent is not optionally substituted aryl), optionally substituted cycloalkyl, optionally substituted cycloalkyl lower alkyl, optionally substituted lower alkenyl, optionally substituted lower alkoxy, optionally substituted aryl, optionally substituted aryl lower alkyl, optionally substituted aryloxy, optionally substituted heterocyclic group, optionally substituted heterocyclyl lower alkyl, optionally substituted heterocyclyloxy, hydroxy, optionally substituted amino, optionally substituted phosphoric acid residue, aryl substituted with optionally substituted phosphoric acid residue, aralkyl substituted with optionally substituted phosphoric acid residue, hydroxy substituted with optionally substituted phosphoric acid residue, amino substituted with optionally substituted phosphoric acid residue, or lower alkyl substituted with optionally substituted phosphoric acid residue (wherein the lower alkyl may be intervened by a heteroatom group selected from the group consisting of CO, O, S, SO, SO2, NRa (wherein Ra is hydrogen or lower alkyl), —N═, and ═N—);
• Z2 is optionally substituted lower alkylene or optionally substituted lower alkenylene that may be intervened by a heteroatom group selected from the group consisting of O, S, SO, SO2, NR5 (wherein R5 is hydrogen, optionally substituted lower alkyl, optionally substituted cycloalkyl, optionally substituted cycloalkyl lower alkyl, optionally substituted lower alkenyl, optionally substituted lower alkoxy, optionally substituted aryl, optionally substituted aryl lower alkyl, optionally substituted aryloxy, optionally substituted heterocyclic group, optionally substituted heterocyclyl lower alkyl, optionally substituted heterocyclyloxy, hydroxy, optionally substituted amino, optionally substituted phosphoric acid residue, aryl substituted with optionally substituted phosphoric acid residue, aralkyl substituted with optionally substituted phosphoric acid residue, hydroxy substituted with optionally substituted phosphoric acid residue, amino substituted with optionally substituted phosphoric acid residue, or lower alkyl substituted with optionally substituted phosphoric acid residue (wherein the lower alkyl may be intervened by a heteroatom group selected from the group consisting of CO, O, S, SO, SO2, NR5 (wherein R5 is, independent of R4, selected from the same substituent group as R4), —N═, and ═N—)), —N═, and ═N—;
• XA is a group selected from the following group:
• XA1:
• a single bond;
• XA2:
• a group selected from C═O and C═S;
• XA3:
• a heteroatom group selected from O, S, SO, SO2, and NR1′ wherein R1′ is hydrogen or lower alkyl,
• XA4:
• a group formed by linking the same or different, two or more groups selected from XA2 and XA3,
• XA5:
• a group selected from —N═N—, —C(R1′)═N—, or —N═C(R1′)— wherein R1′ is hydrogen or lower alkyl;
• XA6:
• optionally substituted lower alkylene or optionally substituted lower alkenylene,
• XA7:
• XA6 by one or any two or more groups selected from XA2, XA3, XA4, and XA5;
• and
• XA8:
• a spacer consisting of any combination of XA1 to XA7;
• Q is a group selected from the following group:
• Q1:
• a carbocyclic group that may be substituted and may be condensed;
• and
• Q2:
• a heterocyclic group that may be substituted and may be condensed,
• with the proviso that the case where —XA-Q is —CONR1—X—R2 (wherein
• R1 is hydrogen or lower alkyl,
• X is a single bond;
• a heteroatom group selected from O, S, SO, SO2, and NH;
• or lower alkylene or lower alkenylene that may be intervened by the heteroatom group, and
• R2 is optionally substituted aryl)
• is excluded;
• R3 is hydrogen, halogen, hydroxy, optionally substituted lower alkyl, optionally substituted cycloalkyl, optionally substituted lower alkenyl, optionally substituted lower alkoxy, optionally substituted lower alkenyloxy, optionally substituted aryl, optionally substituted aryloxy, optionally substituted heterocyclic group, optionally substituted heterocyclyloxy, or optionally substituted amino;
• R4 may be taken together with the Z2 part to form a ring, and in this case, Compound (QI) is represented by the following formula (QI-1) or (QI-11):
• wherein
• the A ring is an optionally substituted heterocycle;
• R14 and RX are each independently hydrogen, optionally substituted lower alkyl, optionally substituted cycloalkyl, optionally substituted cycloalkyl lower alkyl, optionally substituted lower alkenyl, optionally substituted lower alkoxy, optionally substituted lower alkenyloxy, optionally substituted aryl, optionally substituted aryl lower alkyl, optionally substituted aryloxy, optionally substituted heterocyclic group, optionally substituted heterocyclyl lower alkyl, optionally substituted heterocyclyloxy, optionally substituted phosphoric acid residue, aryl substituted with optionally substituted phosphoric acid residue, aralkyl substituted with optionally substituted phosphoric acid residue, hydroxy substituted with optionally substituted phosphoric acid residue, amino substituted with optionally substituted phosphoric acid residue, lower alkyl substituted with optionally substituted phosphoric acid residue (wherein the lower alkyl may be intervened by a heteroatom group selected from the group consisting of O, S, SO, SO2, NR5 (wherein R5 is, independent of R4, selected from the same substituent group as R4), —N═, and ═N—), hydroxy, optionally substituted amino, optionally substituted lower alkylcarbonyl, optionally substituted cycloalkyl carbonyl, optionally substituted cycloalkyl lower alkylcarbonyl, optionally substituted lower alkoxycarbonyl, optionally substituted aryl carbonyl, optionally substituted aryl lower alkylcarbonyl, optionally substituted aryloxycarbonyl, optionally substituted heterocyclylcarbonyl, optionally substituted heterocyclyl lower alkylcarbonyl, optionally substituted heterocyclyloxycarbonyl, or optionally substituted aminocarbonyl;
• the broken line represents the presence or absence of a bond;
• with the proviso that when the broken line represents the presence of a bond, RX is not present;
• XA and Q are defined the same as above;
• R3 is hydrogen, halogen, hydroxy, optionally substituted lower alkyl, optionally substituted cycloalkyl, optionally substituted lower alkenyl, optionally substituted lower alkoxy, optionally substituted lower alkenyloxy, optionally substituted aryl, optionally substituted aryloxy, optionally substituted heterocyclic group, optionally substituted heterocyclyloxy, or optionally substituted amino;
• wherein
• the D ring is an optionally substituted heterocycle;
• XA and Q are defined the same as above;
• R3 is hydrogen, halogen, hydroxy, optionally substituted lower alkyl, optionally substituted cycloalkyl, optionally substituted lower alkenyl, optionally substituted lower alkoxy, optionally substituted lower alkenyloxy, optionally substituted aryl, optionally substituted aryloxy, optionally substituted heterocyclic group, optionally substituted heterocyclyloxy, or optionally substituted amino;
• alternatively, Z2 may be a linking group consisting of B1 and B2, and in this case, Compound (QI) is represented by the following formula (QI-B):
• wherein
• the broken line represents the presence or absence of a bond;
• either one of B1 and B2 is CR20R21 and the other is NR22, and in this case, the broken line is not present;
• when B2 is NR22, R4 and R22 may be taken together to form an optionally substituted heterocycle;
• when B2 is CHR21, R4 and R21 may be taken together to form an optionally substituted heterocycle;
• or B1 and B2 are each independently C, CR23, or N, and in this case, the B1 and B2 parts may be taken together to form an optionally substituted heterocycle;
• R20, R21, R22, and R23 are each independently hydrogen, optionally substituted lower alkyl, optionally substituted cycloalkyl, optionally substituted cycloalkyl lower alkyl, optionally substituted lower alkenyl, optionally substituted lower alkoxy, optionally substituted lower alkenyloxy, optionally substituted aryl, optionally substituted aryl lower alkyl, optionally substituted aryloxy, optionally substituted heterocyclic group, optionally substituted heterocyclyl lower alkyl, optionally substituted heterocyclyloxy, optionally substituted phosphoric acid residue, aryl substituted with optionally substituted phosphoric acid residue, aralkyl substituted with optionally substituted phosphoric acid residue, hydroxy substituted with optionally substituted phosphoric acid residue, amino substituted with optionally substituted phosphoric acid residue, lower alkyl substituted with optionally substituted phosphoric acid residue (wherein the lower alkyl may be intervened by a heteroatom group selected from the group consisting of O, S, SO, SO2, NR5 (wherein R5 is, independent of R4, selected from the same substituent group as R4), —N═, and ═N—), hydroxy, optionally substituted amino, optionally substituted lower alkylcarbonyl, optionally substituted cycloalkyl carbonyl, optionally substituted cycloalkyl lower alkylcarbonyl, optionally substituted lower alkoxycarbonyl, optionally substituted aryl carbonyl, optionally substituted aryl lower alkylcarbonyl, optionally substituted aryloxycarbonyl, optionally substituted heterocyclylcarbonyl, optionally substituted heterocyclyl lower alkylcarbonyl, optionally substituted heterocyclyloxycarbonyl, optionally substituted aminocarbonyl, substituted (thio)urea, or substituted sulfonyl;
• other symbols are defined the same as above,
• or a pharmaceutically acceptable salt thereof, or a solvate thereof.