Bicyclic heteroaromatic ring derivative

1. A compound represented by Formula (1):

wherein

X represents N or CH;

Q 1 represents N or CH;

Q 2 represents N or CR 3 ;

L represents —SO 2 —, —SO 2 C(R 8 ) 2 —, or —SO 2 NR 8 —;

R 1 represents H; a C 1 -C 6 alkyl group, wherein the alkyl group is optionally substituted with one or more substituents selected from the group consisting of a halogen atom, a hydroxy group, a C 1 -C 6 alkyl group, a C 1 -C 6 alkoxy group, a haloC 1 -C 6 alkyl group, a cyano group, a carboxy group, a C 3 -C 10 cycloalkyl group, a 3- to 10-membered heterocycloalkyl group, a C 3 -C 10 cycloalkyloxy group, a 3- to 10-membered heterocycloalkyloxy group, —C(O)R 9 , and —C(O)NR 10 R 11 ; a C 3 -C 6 cycloalkyl group, wherein the cycloalkyl group is optionally substituted with one or more substituents selected from the group consisting of a haloC 1 -C 6 alkyl group, a C 1 -C 6 alkoxy group, a hydroxy group, and a cyano group; or a C 2 -C 6 alkenyl group, wherein the alkenyl group is optionally substituted with one or more substituents selected from the group consisting of a halogen atom, a C 1 -C 6 alkoxy group, a cyano group, a carboxy group, a C 3 -C 10 cycloalkyl group, a 3- to 10-membered heterocycloalkyl group, a C 3 -C 10 cycloalkyloxy group, a 3- to 10-membered heterocycloalkyloxy group, —C(O)R 9 , and —C(O)NR 10 R 11 ;

R 2 represents a C 1 -C 6 alkyl group;

R 3 represents H; a C 1 -C 6 alkyl group, wherein the alkyl group is optionally substituted with one or more substituents selected from the group consisting of a halogen atom, a hydroxy group, a C 1 -C 6 alkoxy group, a haloC 1 -C 6 alkyl group, a cyano group, a C 3 -C 10 cycloalkyl group, a 3- to 10-membered heterocycloalkyl group, a C 3 -C 10 cycloalkyloxy group, a 3- to 10-membered heterocycloalkyloxy group, —C(O)R 9 , and —C(O)NR 10 R 11 ; a hydroxy group; a C 1 -C 6 alkoxy group; a haloC 1 -C 6 alkyl group; a cyano group; a C 3 -C 10 cycloalkyl group; a 3- to 10-membered heterocycloalkyl group; a C 3 -C 10 cycloalkyloxy group; a 3- to 10-membered heterocycloalkyloxy group; —C(O)R 9 ; —C(O)NR 10 R 11 ; or a halogen atom;

R 4 represents H, a halogen atom, a C 1 -C 6 alkoxy group, a deuterated C 1 -C 6 alkoxy group, a C 1 -C 6 alkyl group, a haloC 1 -C 6 alkyl group, a haloC 1 -C 6 alkoxy group, a hydroxyC 1 -C 6 alkyl group, a hydroxy group, a cyano group, —C(O)R 9 , —C(O)NR 10 R 11 , or NR 10 R 11 ;

when Q 2 is CR 3 , R 3 and R 4 may be joined together to form a ring;

G represents —R 5 —R 6 —R 7 ; a hydroxyC 1 -C 6 alkyl group, wherein the hydroxyC 1 -C 6 alkyl group is optionally substituted with W 1 and W 2 , wherein W 1 and W 2 are each independently selected from the group consisting of hydrogen, a C 1 -C 6 alkyl group, a deuterated C 1 -C 6 alkyl group, a haloC 1 -C 6 alkyl group, and a hydroxyC 1 -C 6 alkyl group, wherein W 1 and W 2 may be joined together to form a ring, and the ring formed by W 1 and W 2 is optionally substituted with one or more halogen atoms; a C 3 -C 6 cycloalkyl group, wherein the C 3 -C 6 cycloalkyl group is optionally substituted with W 3 and W 4 , wherein W 3 and W 4 are each independently selected from the group consisting of hydrogen, a halogen atom, a hydroxy group, a C 1 -C 6 alkyl group, a C 1 -C 6 acyl group, a hydroxyC 1 -C 6 alkyl group, a C 1 -C 6 alkoxy group, a C 1 -C 6 alkoxycarbonyl group, —SO 2 R 12 , and an oxo group, and W 3 and W 4 may be joined together to form a ring; a C 5 -C 8 bicycloalkyl group, wherein the C 5 -C 8 bicycloalkyl group is optionally substituted with W 3 and W 4 , wherein W 3 and W 4 are each independently selected from the group consisting of hydrogen, a halogen atom, a hydroxy group, a C 1 -C 6 alkyl group, a C 1 -C 6 acyl group, a hydroxyC 1 -C 6 alkyl group, a C 1 -C 6 alkoxy group, a C 1 -C 6 alkoxycarbonyl group, —SO 2 R 12 , and an oxo group, and W 3 and W 4 may be joined together to form a ring; a 3- to 10-membered heterocycloalkyl group, wherein the 3- to 10-membered heterocycloalkyl group is optionally substituted with W 3 and W 4 , wherein W 3 and W 4 are each independently selected from the group consisting of hydrogen, a halogen atom, a hydroxy group, a C 1 -C 6 alkyl group, a C 1 -C 6 acyl group, a hydroxyC 1 -C 6 alkyl group, a C 1 -C 6 alkoxy group, a C 1 -C 6 alkoxycarbonyl group, —SO 2 R 12 , —C(O)N(R 13 ) 2 , and an oxo group, and W 3 and W 4 may be joined together to form a ring; a C 1 -C 6 alkyl group, wherein the C 1 -C 6 alkyl group is optionally substituted with W 5 and W 6 , wherein W 5 and W 6 are each independently selected from the group consisting of H, a cyano group, a hydroxyC 1 -C 6 alkyl group, a C 1 -C 6 alkyl group, a C 1 -C 6 alkoxycarbonyl group, a carboxy group, and —C(O)N(R 13 ) 2 , and W 5 and W 6 may be joined together to form a ring; a phenyl group, wherein the phenyl group is optionally substituted with one or more substituents selected from the group consisting of a halogen atom, a C 1 -C 6 alkyl group, a hydroxyC 1 -C 6 alkyl group, a C 1 -C 6 acyl group, a carboxy group, a hydroxy group, a haloC 1 -C 6 alkyl group, a cyano group, a C 3 -C 10 cycloalkyl group, a 3-, to 10-membered heterocycloalkyl group, —NR 10 R 11 , —C(O)R 9 , —C(O)NR 10 R 11 , a C 1 -C 6 alkoxycarbonyl group, —SO 2 R 12 , and a C 1 -C 6 alkoxy group; or a heteroaryl group, wherein the heteroaryl group is optionally substituted with one or more substituents selected from the group consisting of a halogen atom, a C 1 -C 6 alkyl group, a hydroxyC 1 -C 6 alkyl group, a C 1 -C 6 acyl group, a carboxy group, a hydroxy group, a haloC 1 -C 6 alkyl group, a cyano group, a C 3 -C 10 cycloalkyl group, a 3- to 10-membered heterocycloalkyl group, —NR 10 R 11 , —C(O)R 9 , —C(O)NR 10 R 11 , a C 1 -C 6 alkoxycarbonyl group, —SO 2 R 12 , and a C 1 -C 6 alkoxy group;

R 5 represents a hydroxyC 1 -C 6 alkylene group, wherein the hydroxyC 1 -C 6 alkylene group is optionally substituted with W 1 and W 2 , wherein W 1 and W 2 are each independently selected from the group consisting of H, a C 1 -C 6 alkyl group, a deuterated C 1 -C 6 alkyl group, a haloC 1 -C 6 alkyl group, and a hydroxyC 1 -C 6 alkyl group, and W 1 and W 2 may be joined together to form a ring, and the ring formed by W 1 and W 2 is optionally substituted with one or more halogen atoms; a C 3 -C 6 cycloalkylene group, wherein the C 3 -C 6 cycloalkylene group is optionally substituted with W 3 and W 4 , wherein W 3 and W 4 are each independently selected from the group consisting of H, a halogen atom, a hydroxy group, a C 1 -C 6 alkyl group, a C 1 -C 6 acyl group, a hydroxyC 1 -C 6 alkyl group, a C 1 -C 6 alkoxy group, a C 1 -C 6 alkoxycarbonyl group, —SO 2 R 12 , and an oxo group, and W 3 and W 4 may be joined together to form a ring; a C 5 -C 8 bicycloalkylene group, wherein the C 5 -C 8 bicycloalkylene group is optionally substituted with W 3 and W 4 , wherein W 3 and W 4 are each independently selected from the group consisting of H, a halogen atom, a hydroxy group, a C 1 -C 6 alkyl group, a C 1 -C 6 acyl group, a hydroxyC 1 -C 6 alkyl group, a C 1 -C 6 alkoxy group, a C 1 -C 6 alkoxycarbonyl group, —SO 2 R 12 , and an oxo group, and W 3 and W 4 may be joined together to form a ring; a 3- to 10-membered heterocycloalkylene group, wherein the 3- to 10-membered heterocycloalkylene group is optionally substituted with W 3 and W 4 , wherein W 3 and W 4 are each independently selected from the group consisting of H, a halogen atom, a hydroxy group, a C 1 -C 6 alkyl group, a C 3 -C 10 cycloalkyl group, a C 1 -C 6 acyl group, a hydroxyC 1 -C 6 alkyl group, a C 1 -C 6 alkoxy group, a C 1 -C 6 alkoxycarbonyl group, —SO 2 R 12 , —C(O)N(R 13 ) 2 , and an oxo group, and W 3 and W 4 may be joined together to form a ring; a C 1 -C 6 alkylene group, wherein the C 1 -C 6 alkylene group is optionally substituted with W 5 and W 6 , wherein W 5 and W 6 are each independently selected from the group consisting of H, a cyano group, a hydroxyC 1 -C 6 alkyl group, a C 1 -C 6 alkyl group, a C 1 -C 6 alkoxycarbonyl group, a carboxy group, and —C(O)N(R 13 ) 2 , and W 5 and W 6 may be joined together to form a ring; a phenylene group, wherein the phenylene group is optionally substituted with one or more substituents selected from the group consisting of a halogen atom, a C 1 -C 6 alkyl group, a hydroxyC 1 -C 6 alkyl group, a C 1 -C 6 acyl group, a carboxy group, a hydroxy group, a haloC 1 -C 6 alkyl group, a cyano group, a C 3 -C 10 cycloalkyl group, a 3- to 10-membered heterocycloalkyl group, —NR 10 R 11 , —C(O)R 9 , —C(O)NR 10 R 11 , a C 1 -C 6 alkoxycarbonyl group, —SO 2 R 12 , and a C 1 -C 6 alkoxy group; or a heteroarylene group, wherein the heteroarylene group is optionally substituted with one or more substituents selected from the group consisting of a halogen atom, a C 1 -C 6 alkyl group, a hydroxyC 1 -C 6 alkyl group, a C 1 -C 6 acyl group, a carboxy group, a hydroxy group, a haloC 1 -C 6 alkyl group, a cyano group, a C 3 -C 10 cycloalkyl group, a 3- to 10-membered heterocycloalkyl group, —NR 10 R 11 , —C(O)R 9 , —C(O)NR 10 R 11 , a C 1 -C 6 alkoxycarbonyl group, —SO 2 R 12 , and a C 1 -C 6 alkoxy group;

R 6 represents a bond or a C 3 -C 6 cycloalkylene group;

R 7 represents H or a hydroxy group;

each R 8 independently represents H or a C 1 -C 6 alkyl group;

R 9 represents H, a hydroxy group, a C 1 -C 6 alkyl group, a C 1 -C 6 alkoxy group, or a C 3 -C 6 cycloalkoxy group;

R 10 represents H or a C 1 -C 6 alkyl group;

R 11 represents H or a C 1 -C 6 alkyl group;

R 12 represents H or a C 1 -C 6 alkyl group; and

each R 13 independently represents H, a C 1 -C 6 alkyl group, or a hydroxyC 1 -C 6 alkyl group,

a pharmacologically acceptable salt of the compound, a hydrate of the compound or a hydrate of the salt.

2. The compound, a pharmacologically acceptable salt of the compound, a hydrate of the compound or a hydrate of the salt according to claim 1 , wherein in Formula (1), Q 1 is CH, Q 2 is CR 3 , and R 3 is H .

3. The compound, a pharmacologically acceptable salt of the compound, a hydrate of the compound or a hydrate of the salt according to claim 1 , wherein in Formula (1), X is N.

4. The compound, a pharmacologically acceptable salt of the compound, a hydrate of the compound or a hydrate of the salt according to claim 1 , wherein in Formula (1), R 2 is a methyl group.

5. The compound, a pharmacologically acceptable salt of the compound, a hydrate of the compound or a hydrate of the salt according to claim 1 , wherein in Formula (1),

X represents N;

Q 1 represents CH;

Q 2 represents CR 3 ;

L represents —SO 2 —;

R 1 represents a C 1 -C 6 alkyl group, wherein the alkyl group is optionally substituted with one or more substituents selected from the group consisting of a halogen atom, a hydroxy group, a C 1 -C 6 alkoxy group, a haloC 1 -C 6 alkyl group, a cyano group, a 3- to 10-membered heterocycloalkyloxy group, —C(O)R 9 , and —C(O)NR 10 R 11 ;

R 2 represents a methyl group;

R 3 represents H;

R 4 represents a C 1 -C 6 alkoxy group, a C 1 -C 6 alkyl group, or a haloC 1 -C 6 alkyl group; and

G represents a hydroxyC 1 -C 6 alkyl group, wherein the hydroxyC 1 -C 6 alkyl group is optionally substituted with W 1 and W 2 , wherein W 1 and W 2 are each independently H or a C 1 -C 6 alkyl group, and W 1 and W 2 may be joined together to form a ring, and the ring formed by W 1 and W 2 is optionally substituted with one or more halogen atoms.

6. The compound, a pharmacologically acceptable salt of the compound, a hydrate of the compound or a hydrate of the salt according to claim 5 , wherein in Formula (1), R 4 is a C 1 -C 6 alkoxy group.

7. The compound, a pharmacologically acceptable salt of the compound, a hydrate of the compound or a hydrate of the salt according to claim 1 , wherein in Formula (1),

X represents N;

Q 1 represents CH;

Q 2 represents CR 3 ;

L represents —SO 2 —, —SO 2 NR 8 —, or —SO 2 C(R 8 ) 2 —;

R 1 represents a C 1 -C 6 alkyl group, wherein the alkyl group is optionally substituted with one or more hydroxy groups or C 1 -C 6 alkoxy groups;

R 2 represents a methyl group;

R 3 represents H or a halogen atom;

R 4 represents a C 1 -C 6 alkoxy group, a C 1 -C 6 alkyl group, a haloC 1 -C 6 alkyl group, or a haloC 1 -C 6 alkoxy group; and

G represents a hydroxyC 1 -C 6 alkyl group, wherein the hydroxyC 1 -C 6 alkyl group is optionally substituted with W 1 and W 2 , wherein W 1 and W 2 are each independently H or a C 1 -C 6 alkyl group, and W 1 and W 2 may be joined together to form a ring, and the ring formed by W 1 and W 2 is optionally substituted with one or more halogen atoms; a C 3 -C 6 cycloalkyl group, wherein the C 3 -C 6 cycloalkyl group is optionally substituted with W 3 and W 4 , wherein W 3 and W 4 are each independently selected from the group consisting of H, a hydroxy group, a C 1 -C 6 alkyl group, a C 1 -C 6 acyl group, a hydroxyC 1 -C 6 alkyl group, a C 1 -C 6 alkoxycarbonyl group, and —SO 2 R 12 , and W 3 and W 4 may be joined together to form a ring; a 3- to 10-membered heterocycloalkyl group, wherein the 3- to 10-membered heterocycloalkyl group is optionally substituted with W 3 and W 4 , wherein W 3 and W 4 are each independently selected from the group consisting of H, a hydroxy group, a C 1 -C 6 alkyl group, a C 1 -C 6 acyl group, a hydroxyC 1 -C 6 alkyl group, a C 1 -C 6 alkoxycarbonyl group, —SO 2 R 12 , and —C(O)N(R 13 ) 2 , and W 3 and W 4 may be joined together to form a ring; a C 1 -C 6 alkyl group, wherein the C 1 -C 6 alkyl group is optionally substituted with W 5 and W 6 , wherein W 5 and W 6 are each independently selected from the group consisting of H, a cyano group, a hydroxyC 1 -C 6 alkyl group, a C 1 -C 6 alkyl group, a C 1 -C 6 alkoxycarbonyl group, a carboxy group, and —C(O)N(R 13 ) 2 , and W 5 and W 6 may be joined together to form a ring; or a heteroaryl group, wherein the heteroaryl group is optionally substituted with one or more substituents selected from the group consisting of a halogen atom, a C 1 -C 6 alkyl group, a hydroxyC 1 -C 6 alkyl group, a C 1 -C 6 acyl group, a carboxy group, a hydroxy group, a haloC 1 -C 6 alkyl group, a cyano group, a C 3 -C 10 cycloalkyl group, a 3- to 10-membered heterocycloalkyl group, —NR 10 R 11 , —C(O)R 9 , —C(O)NR 10 R 11 , a C 1 -C 6 alkoxycarbonyl group, —SO 2 R 12 , and a C 1 -C 6 alkoxy group.

8. The compound, a pharmacologically acceptable salt of the compound, a hydrate of the compound or a hydrate of the salt according to claim 1 , wherein in Formula (1),

X represents CH;

Q 1 represents N or CH;

Q 2 represents N or CR 3 ;

L represents —SO 2 —, —SO 2 NR 8 —, or —SO 2 C(R 8 ) 2 —;

R 1 represents H; a C 1 -C 6 alkyl group, wherein the alkyl group is optionally substituted with one or more substituents selected from the group consisting of a halogen atom, a hydroxy group, a C 1 -C 6 alkoxy group, and a 3- to 10-membered heterocycloalkyloxy group; a C 3 -C 6 cycloalkyl group, wherein the cycloalkyl group is optionally substituted with one or more substituents selected from the group consisting of a C 1 -C 6 alkoxy group and a hydroxy group; or

a C 2 -C 6 alkenyl group;

R 2 represents a C 1 -C 6 alkyl group;

R 3 represents H or a halogen atom;

R 4 represents a halogen atom, a C 1 -C 6 alkoxy group, a C 1 -C 6 alkyl group, a haloC 1 -C 6 alkyl group, a haloC 1 -C 6 alkoxy group, a cyano group, or NR 10 R 11 ;

G represents a hydroxyC 1 -C 6 alkyl group, wherein the hydroxyC 1 -C 6 alkyl group is optionally substituted with W 1 and W 2 , wherein W 1 and W 2 are each independently H or a C 1 -C 6 alkyl group, and W 1 and W 2 may be joined together to form a ring, and the ring formed by W 1 and W 2 is optionally substituted with one or more halogen atoms; a C 3 -C 6 cycloalkyl group, wherein the C 3 -C 6 cycloalkyl group is optionally substituted with W 3 and W 4 , wherein W 3 and W 4 are each independently hydrogen, a hydroxy group, or a C 1 -C 6 alkoxy group, and W 3 and W 4 may be joined together to form a ring; a 3- to 10-membered heterocycloalkyl group; a phenyl group, wherein the phenyl group is optionally substituted with one or more substituents selected from the group consisting of a halogen atom, a C 1 -C 6 alkyl group, a hydroxyC 1 -C 6 alkyl group, a C 1 -C 6 acyl group, a carboxy group, a hydroxy group, a haloC 1 -C 6 alkyl group, a cyano group, a C 3 -C 10 cycloalkyl group, a 3- to 10-membered heterocycloalkyl group, —NR 10 R 11 , —C(O)R 9 , —C(O)NR 10 R 11 , a C 1 -C 6 alkoxycarbonyl group, —SO 2 R 12 , and a C 1 -C 6 alkoxy group; or a heteroaryl group, wherein the heteroaryl group is optionally substituted with one or more substituents selected from the group consisting of a halogen atom, a C 1 -C 6 alkyl group, a hydroxyC 1 -C 6 alkyl group, a C 1 -C 6 acyl group, a carboxy group, a hydroxy group, a haloC 1 -C 6 alkyl group, a cyano group, a C 3 -C 10 cycloalkyl group, a 3- to 10-membered heterocycloalkyl group, —NR 10 R 11 , —C(O)R 9 , —C(O)NR 10 R 11 , a C 1 -C 6 alkoxycarbonyl group, —SO 2 R 12 , and a C 1 -C 6 alkoxy group;

R 8 represents H or a C 1 -C 6 alkyl group;

R 10 represents H or a C 1 -C 6 alkyl group; and

R 11 represents H or a C 1 -C 6 alkyl group.

9. The compound, a pharmacologically acceptable salt of the compound, a hydrate of the compound or a hydrate of the salt according to claim 8 , wherein in Formula (1), Q 1 is CH, and Q 2 is N.

10. The compound, a pharmacologically acceptable salt of the compound, a hydrate of the compound or a hydrate of the salt according to claim 1 , wherein the compound represented by Formula (1) is any one of the compounds listed in the following Tables 1 to 11:

TABLE 1

TABLE 2

TABLE 3

TABLE 4

TABLE 5

TABLE 6

TABLE 7

TABLE 8

TABLE 9

TABLE 10

TABLE 11

11. A pharmaceutical composition comprising the compound, a pharmacologically acceptable salt of the compound, a hydrate of the compound or a hydrate of the salt according to claim 1 as an active ingredient, and a pharmacologically acceptable carrier.

12. An antiviral agent against a virus belonging to the family Picornaviridae, comprising the compound, a pharmacologically acceptable salt of the compound, a hydrate of the compound or a hydrate of the salt according to claim 1 as an active ingredient.

13. A method for treating or preventing a viral infection caused by an enterovirus, a rhinovirus, or a coxsackievirus, comprising administering an effective amount of the compound, a pharmacologically acceptable salt of the compound, a hydrate of the compound or a hydrate of the salt according to claim 1 , to a human in need thereof.

14. A method for treating or preventing exacerbation of asthma or COPD, comprising administering an effective amount of the compound, a pharmacologically acceptable salt of the compound, a hydrate of the compound or a hydrate of the salt according to claim 1 , to a human in need thereof.