Coumarin derivative having antitumor activity

1. A compound represented by general formula (11) below or a pharmaceutically acceptable salt thereof:

wherein:

G 1 and G 2 are each independently —CR 1 ═;

G 3 is CR 1 ;

G 8 is —C(-G 9 —X)═;

X is a C 1-6 alkyl group (where the C 1-6 alkyl group may optionally be substituted with a group selected from a halogen atom, a hydroxy group, a cyano group and —NR 56 R 57 ), an aryl group, a heterocyclic group, R 31 CS—, R 31 CO—, R 33 R 34 NCS—, R 33 R 34 NC═NH—, R 3 R 4 NCO— or R 33 R 34 NCO 2 —;

G 9 is a single bond, an oxygen atom, a sulfur atom, —(CR 35 R 36 ) l — (where l represents an integer of 1 to 3) or —NR 37 —;

Ring G 6 is a 6-membered nitrogen containing hereroaryl,

A is a group represented by general formula (2) below or a group represented by general formula (3) below:

G 4 is an oxygen atom or a sulfur atom and G 5 is an oxygen atom;

G 7 is, —CR 42 R 43 —

R 1 is a hydrogen atom, a halogen atom, a cyano group, a C 1-6 alkyl group (where the C 1-6 alkyl group may optionally be substituted with a group selected from a halogen atom, a hydroxy group and —NR 46 R 47 ), a C 2-7 alkenyl group, a carbamoyl group or a C 2-7 alkynyl group (where the C 2-7 alkynyl group may optionally be substituted with a C 1-4 acyl group);

R 2 is a hydroxy group, a C 1-6 alkoxy group, —NR 48 R 49 or a C 1-6 alkyl group (where the C 1-6 alkyl group may optionally be substituted with a group selected from a halogen atom, a hydroxy group, a C 1-6 alkoxy group, a formyl group, —CO 2 R 50 and —CO 2 NR 51 R 52 );

R 3 , R 4 , R 6 , R 7 , R 9 , R 10 , R 31 , R 46 and R 47 are each independently a hydrogen atom, a C 1-6 alkoxy group, a C 3-8 cycloalkyl group or a C 1-6 alkyl group (where the C 1-6 alkyl group may optionally be substituted with a group selected from a cyano group, a halogen atom, a hydroxy group, a C 1-6 alkoxy group, —NR 13 R 14 , —CONR 28 R 29 and an aryl group);

R 33 and R 34 are each independently a hydrogen atom, a C 1-6 alkyl group or an aryl group;

the combination of R 3 and R 4 , combination of R 6 and R 7 , combination of R 9 and R 10 , combination of R 33 and R 34 , and combination of R 46 and R 47 may form, together with the nitrogen atom to which they are bonded, a 4- to 6-membered heterocyclic group having at least one nitrogen atom (where the heterocyclic group may optionally be fused with a benzene ring);

one R 35 group and one R 36 group are each independently a hydrogen atom, a halogen atom or a C 1-6 alkyl group;

R 13 ,R 14 ,R 56 and R 57 are each independently a hydrogen atom, a C 1-6 alkyl group, —COR 32 or —CO 2 R 32 ; and

R 5 , R 8 , R 28 , R 29 , R 32 , R 37 , R 48 , R 49 , R 50 , R 51 , and R 52 are each independently a hydrogen atom or a C 1-6 alkyl group;

R 42 and R 43 are hydrogen.

2. The compound or pharmaceutically acceptable salt thereof according to claim 1 , wherein the compound represented by general formula (11) is a compound represented by general formula (1) below:

wherein:

X is a heteroaryl group or R 3 R 4 NCO—;

Y 1 and Y 2 are each independently —N═ or —CR 11 ═;

Y 3 and Y 4 may be the same or different, and are each —CR 12 ═;

A is a group represented by general formula (2) below or a group represented by general formula (3) below:

R 1 is a hydrogen atom, a halogen atom, a cyano group, a C 1-6 alkyl group, a C 2-7 alkenyl group, a carbamoyl group or a C 2-7 alkynyl group (where the C 2-7 alkynyl group may optionally be substituted with a C 1-4 acyl group);

R 2 is a C 1-6 alkyl group optionally substituted with a halogen atom;

R 3 , R 4 , R 6 , R 7 , R 9 and R 10 are each independently a hydrogen atom, a C 1-6 alkoxy group, a C 3-8 cycloalkyl group or a C 1-6 alkyl group (where the C 1-6 alkyl group may optionally be substituted with a group selected from a cyano group, a halogen atom, a hydroxy group, a C 1-6 alkoxy group and —NR 13 R 14 );

the combination of R 3 and R 4 , combination of R 6 and R 7 , and combination of R 9 and R 10 may form, together with the nitrogen atom to which they are bonded, a 4- to 6-membered heterocyclic group having at least one nitrogen atom;

R 5 , R 8 , R 13 and R 14 are each independently a hydrogen atom or a C 1-6 alkyl group;

R 11 is a hydrogen atom, a halogen atom, a C 1-6 alkyl group, a C 1-4 acyl group, a C 1-4 acyloxy group or —NR 15 R 16 ;

R 12 is a hydrogen atom, a halogen atom or a C 1-6 alkyl group; and

R 15 and R 16 are each independently a hydrogen atom or a C 1-4 acyl group.

3. The compound or pharmaceutically acceptable salt thereof according to claim 2 , wherein R 1 is a hydrogen atom, a halogen atom or a C 1-6 alkyl group.

4. The compound or pharmaceutically acceptable salt thereof according to claim 2 , wherein R 5 or R 8 is a hydrogen atom.

5. The compound or pharmaceutically acceptable salt thereof according to claim 2 , wherein R 3 , R 4 , R 6 , R 7 , R 9 and R 10 are each independently a hydrogen atom or a C 1-6 alkyl group.

6. The compound or pharmaceutically acceptable salt thereof according to claim 2 , wherein X is a thiazol-2-yl group, a pyrimidin-2-yl group, a 2-pyridyl group or R 3 R 4 NCO—(where R 3 and R 4 have the same definitions as above).

7. The compound or pharmaceutically acceptable salt thereof according to claim 6 , wherein both R 3 and R 4 are a methyl group.

8. The compound or pharmaceutically acceptable salt thereof according to claim 2 , wherein R 2 is a C 1-6 alkyl group optionally substituted with a fluorine atom.

9. The compound or pharmaceutically acceptable salt thereof according to claim 8 , wherein R 2 is —CH 3 , —CH 2 F or —CH 2 CH 3 .

10. The compound or pharmaceutically acceptable salt thereof according to claim 2 , which is selected from:

dimethylcarbamic acid 4-methyl-3-{2-(methylaminosulfonyl)aminopyridin-4-ylmethyl}-2-oxo-2H-1-benzopyran-7-yl ester,

dimethylcarbamic acid 4-methyl-3-{2-(methylaminosulfonyl)aminopyridin-4-ylmethyl}-6-fluoro-2-oxo-2H-1-benzopyran-7-yl ester,

dimethylcarbamic acid 4-methyl-3-{2-(methylaminosulfonyl)aminopyridin-4-ylmethyl}-6-chloro-2-oxo-2H-1-benzopyran-7-yl ester,

dimethylcarbamic acid 4-methyl-3-{6-(methylaminosulfonyl)aminopyridin-2-ylmethyl}-2-oxo-2H-1-benzopyran-7-yl ester,

dimethylcarbamic acid 4-methyl-3-{6-(methylaminosulfonyl)aminopyridin-2-ylmethyl}-6-fluoro-2-oxo-2H-1-benzopyran-7-yl ester,

dimethylcarbamic acid 4-methyl-3-{6-(methylaminosulfonyl)aminopyridin-2-ylmethyl}-6-chloro-2-oxo-2H-1-benzopyran-7-yl ester,

3-{2-(methylaminosulfonyl)aminopyridin-4-ylmethyl}-4-methyl-7-(pyrimidin-2-yloxy)-2-oxo-2H-1-benzopyran,

3-{2-(methylaminosulfonyl)aminopyridin-4-ylmethyl}-4-methyl-7-(pyrimidin-2-yloxy)-6-chloro-2-oxo-2H-1-benzopyran,

3-{2-(methylaminosulfonyl)amino-3-fluoropyridin-4-ylmethyl}-4-methyl-7-(pyrimidin-2-yloxy)-2-oxo-2H-1-benzopyran,

3-{2-(ethylaminosulfonyl)amino-3-fluoropyridin-4-ylmethyl}-4-methyl-7-(pyrimidin-2-yloxy)-2-oxo-2H-1-benzopyran,

3-{2-(isopropylaminosulfonyl)amino-3-fluoropyridin-4-ylmethyl}-4-methyl-7-(pyrimidin-2-yloxy)-2-oxo-2H-1-benzopyran,

3-{2-(methylaminosulfonyl)amino-3-fluoropyridin-4-ylmethyl}-4-methyl-6-fluoro-7-(pyrimidin-2-yloxy)-2-oxo-2H-1-benzopyran,

3-{2-(cyclopropylaminosulfonyl)amino-3-fluoropyridin-4-ylmethyl}-4-methyl-6-fluoro-7-(pyrimidin-2-yloxy)-2-oxo-2H-1-benzopyran, 3-{2-(methylaminosulfonyl)amino-3-fluoropyridin-4-ylmethyl}-4-methyl-6-chloro-7-(pyrimidin-2-yloxy)-2-oxo-2H-1-benzopyran,

3-{2-(methylaminosulfonyl)amino-3-fluoropyridin-4-ylmethyl}-4-methyl-6-methyl-7-(pyrimidin-2-yloxy)-2-oxo-2H-1-benzopyran,

3-{2-(methylaminosulfonyl)amino-3-fluoropyridin-4-ylmethyl}-4-ethyl-6-methyl-7-(pyrimidin-2-yloxy)-2-oxo-2H-1-benzopyran,

3-{2-(cyclopropylaminosulfonyl)amino-3-fluoropyridin-4-ylmethyl}-4-methyl-6-methyl-7-(pyrimidin-2-yloxy)-2-oxo-2H-1-benzopyran,

3-{2-(cyclopropylaminosulfonyl)amino-3-fluoropyridin-4-ylmethyl}-4-methyl-7-(pyrimidin-2-yloxy)-2-oxo-2H-1-benzopyran,

3-{2-(methylaminosulfonyl)amino-3-chloropyridin-4-ylmethyl}-4-methyl-7-(pyrimidin-2-yloxy)-2-oxo-2H-1-benzopyran,

3-{2-(methylaminosulfonyl)aminopyridin-4-ylmethyl}-4-methyl-6-chloro-7-(thiazol-2-yloxy)-2-oxo-2H-1-benzopyran,

3-{2-(methylaminosulfonyl)amino-3-fluoropyridin-4-ylmethyl}-4-methyl-6-methyl-7-(thiazol-2-yloxy)-2-oxo-2H-1-benzopyran,

3-{2-(cyclopropylaminosulfonyl)amino-3-fluoropyridin-4-ylmethyl}-4-methyl-6-methyl-7-(thiazol-2-yloxy)-2-oxo-2H-1-benzopyran,

3-{2-(methylaminosulfonyl)aminopyridin-4-ylmethyl}-4-methyl-6-methyl-7-(thiazol-2-yloxy)-2-oxo-2H-1-benzopyran,

3-{2-(methylaminosulfonyl)amino-3-chloropyridin-4-ylmethyl}-4-methyl-6-methyl-7-(thiazol-2-yloxy)-2-oxo-2H-1-benzopyran,

3-{2-(methylaminosulfonyl)amino-3-fluoropyridin-4-ylmethyl}-4-methyl-7-(5-fluoropyrimidin-2-yloxy)-2-oxo-2H-1-benzopyran,

3-{2-(methylaminosulfonyl)amino-3-fluoropyridin-4-ylmethyl}-4-methyl-7-(4-chloropyrimidin-2-yloxy)-2-oxo-2H-1-benzopyran,

3-{2-(methylaminosulfonyl)amino-3-fluoropyridin-4-ylmethyl}-4-methyl-7-(2,4-dimethoxypyrimidin-6-yloxy)-2-oxo-2H-1-benzopyran,

3-{2-(methylaminosulfonyl)amino-3-fluoropyridin-4-ylmethyl}-4-methyl-7-(benzothiazol-2-yloxy)-2-oxo-2H-1-benzopyran,

3-{2-(methylaminosulfonyl)amino-3-fluoropyridin-4-ylmethyl}-4-methyl-7-(5-bromothiazol-2-yloxy)-2-oxo-2H-1-benzopyran,

3-{2-(methylaminosulfonyl)amino-3-fluoropyridin-4-ylmethyl}-4-methyl-7-(pyrazin-2-yloxy)-2-oxo-2H-1-benzopyran, and

3-{2-(methylaminosulfonyl)amino-3-fluoropyridin-4-ylmethyl}-4-methyl-7-(pyridin-2-yloxy)-2-oxo-2H-1-benzopyran.

11. A pharmaceutical composition comprising the compound or pharmaceutically acceptable salt thereof according to claim 1 as an active ingredient.

12. A pharmaceutical composition comprising the compound or pharmaceutically acceptable salt thereof according to claim 2 as an active ingredient.

13. The compound or pharmaceutically acceptable salt thereof according to claim 2 , which is 3-{2-(methylaminosulfonyl)amino-3-fluoropyridin-4-ylmethyl}-4-methyl-7-(pyrimidin-2-yloxy)-2-oxo-2H-1-benzopyran.