Anticancer agent

1. A compound represented by the formula (IA):

wherein

each R 1 is independently

hydrogen,

halogen,

hydroxy,

amino,

cyano,

nitro,

C 1-12 alkyl,

C 2-6 alkenyl,

C 2-6 alkynyl,

C 3-7 cycloalkyl,

C 3-7 cycloalkenyl,

aryl,

a heterocyclyl group,

C 1-6 alkoxy,

aryloxy,

C 1-6 alkylthio, or

arylthio, or

two R 1 bonded to the adjacent carbon atoms on a benzene ring are optionally joined to form C 1-4 alkylenedioxy,

R 2 is

C 1-12 alkyl optionally substituted by substituent(s) selected from substituent group α,

C 2-6 alkenyl optionally substituted by substituent(s) selected from substituent group α,

C 2-6 alkynyl optionally substituted by substituent(s) selected from substituent group α,

C 3-7 cycloalkyl optionally substituted by substituent(s) selected from substituent group α,

aryl optionally substituted by substituent(s) selected from substituent group α,

aryl C 1-6 alkyl optionally substituted by substituent(s) selected from substituent group α, or

heterocyclyl optionally substituted by substituent(s) selected from substituent group α,

R 3 is

hydrogen,

halogen,

cyano,

nitro,

C 1-12 alkyl,

C 2-6 alkenyl,

C 2-6 alkynyl,

C 3-7 cycloalkyl,

C 3-7 cycloalkenyl,

aryl,

heterocyclyl,

C 1-6 alkoxy,

aryloxy,

C 1-6 alkylthio, or

arylthio,

n is an integer of 1-4 when R 1 is hydrogen,

n is an integer of 1 or 2 when R 1 is not hydrogen, and

the substituent group α consists of

halogen,

hydroxy,

optionally substituted amino,

carboxy,

C 1-6 alkoxycarbonyl,

sulfo group,

phosphoric acid group,

di C 1-6 alkyl phosphoric acid group,

cyano,

optionally substituted C 1-6 alkyl,

C 3-7 cycloalkyl,

C 3-7 cycloalkyl C 1-6 alkyl,

optionally substituted C 1-6 alkoxy,

C 1-6 alkylthio,

optionally substituted aryl,

optionally substituted aryloxy,

aryl C 1-6 alkoxy,

optionally substituted heterocyclyl,

optionally substituted C 1-6 alkylcarbonyl,

heterocyclylcarbonyl,

optionally substituted C 1-6 alkylcarbonyloxy,

optionally substituted C 3-7 cycloalkylcarbonyloxy,

arylcarbonyloxy,

monocyclic heterocyclylcarbonyloxy,

optionally substituted C 1-6 alkoxycarbonyloxy,

optionally substituted heterocyclyl C 1-6 alkoxycarbonyloxy,

C 3-7 cycloalkyloxycarbonyloxy,

heterocyclyloxycarbonyloxy,

optionally substituted heterocyclyloxy,

tri C 1-6 alkylammonio,

optionally substituted C 1-6 alkylsulfonyl and

C 1-6 alkylsulfamoylcarbonyl,

or a pharmaceutically acceptable salt thereof.

2. A compound represented by the formula (I):

wherein

R 1 is

hydrogen or halogen,

R 2 is

C 1-12 alkyl optionally substituted by substituent(s) selected from substituent group α,

C 2-6 alkenyl optionally substituted by substituent(s) selected from substituent group α,

C 2-6 alkynyl optionally substituted by substituent(s) selected from substituent group α,

C 3-7 cycloalkyl optionally substituted by substituent(s) selected from substituent group α,

aryl optionally substituted by substituent(s) selected from substituent group α,

aryl C 1-6 alkyl optionally substituted by substituent(s) selected from substituent group α, or

a heterocyclyl group optionally substituted by substituent(s) selected from substituent group α,

n is an integer of 1-4 when R 1 is hydrogen,

n is an integer of 1 or 2 when R 1 is not hydrogen, and

the substituent group α consists of

halogen,

hydroxy,

optionally substituted amino,

carboxy,

C 1-6 alkoxycarbonyl,

sulfo group,

phosphoric acid group,

di C 1-6 alkyl phosphoric acid group,

cyano,

optionally substituted C 1-6 alkyl,

C 3-7 cycloalkyl,

C 3-7 cycloalkyl C 1-6 alkyl,

optionally substituted C 1-6 alkoxy,

C 1-6 alkylthio,

optionally substituted aryl,

optionally substituted aryloxy,

aryl C 1-6 alkoxy,

optionally substituted heterocyclyl,

optionally substituted C 1-6 alkylcarbonyl,

heterocyclylcarbonyl,

optionally substituted C 1-6 alkylcarbonyloxy,

optionally substituted C 3-7 cycloalkylcarbonyloxy,

arylcarbonyloxy,

monocyclic heterocyclylcarbonyloxy,

optionally substituted C 1-6 alkoxycarbonyloxy,

optionally substituted heterocyclyl C 1-6 alkoxycarbonyloxy,

C 3-7 cycloalkyloxycarbonyloxy,

heterocyclyloxycarbonyloxy,

optionally substituted heterocyclyloxy,

tri C 1-6 alkylammonio,

optionally substituted C 1-6 alkyl sulfonyl and

C 1-6 alkyl sulfamoylcarbonyl,

or a pharmaceutically acceptable salt thereof.

3. The compound according to claim 2 , wherein the substituent group α consists of

halogen,

hydroxy,

optionally substituted amino,

carboxy,

C 1-6 alkoxycarbonyl,

sulfo group,

phosphoric acid group,

di C 1-6 alkyl phosphoric acid group,

cyano,

C 1-6 alkyl,

C 3-7 cycloalkyl,

C 1-6 alkoxy,

optionally substituted aryl,

optionally substituted aryloxy,

aryl C 1-6 alkoxy,

optionally substituted heterocyclyl,

optionally substituted C 1-6 alkylcarbonyl,

heterocyclylcarbonyl,

optionally substituted C 1-6 alkylcarbonyloxy,

optionally substituted C 3 -7 cycloalkylcarbonyloxy,

monocyclic heterocyclylcarbonyloxy,

optionally substituted C 1-6 alkoxycarbonyloxy,

optionally substituted heterocyclyl C 1-6 alkoxycarbonyloxy,

C 3-7 cycloalkyloxycarbonyloxy,

heterocyclyloxycarbonyloxy,

optionally substituted heterocyclyloxy and

tri C 1-6 alkylammonio,

or a pharmaceutically acceptable salt thereof.

4. The compound according to claim 2 , wherein

R 2 is C 1-6 alkyl optionally substituted by substituent(s) selected from substituent group α, C 2-6 alkenyl optionally substituted by substituent(s) selected from substituent groupα, C 3-7 cycloalkyl optionally substituted by substituent(s) selected from substituent group α, aryl optionally substituted by substituent(s) selected from substituent group α, aryl C 1-6 alkyl optionally substituted by substituent(s) selected from substituent group α, or heterocyclyl optionally substituted by substituent(s) selected from substituent group α, and

the substituent group α consists of halogen, hydroxy, optionally substituted amino, carboxy, sulfo group, phosphoric acid group, cyano, C 1-6 alkyl, C 3-7 cycloalkyl, C 1-6 alkoxy, aryl and heterocyclyl,

or a pharmaceutically acceptable salt thereof.

5. The compound according to claim 2 , wherein R 2 is

(1) C 1-6 alkyl optionally substituted by substituent(s) selected from hydroxy, optionally substituted amino, carboxy, sulfo group, phosphoric acid group, di C 1-6 alkyl phosphoric acid group, heterocyclyl group, optionally substituted C 1-6 alkoxy, optionally substituted C 1-6 alkylcarbonyloxy, monocyclic heterocyclylcarbonyloxy, C 3-7 cycloalkyloxycarbonyloxy and heterocyclyloxycarbonyloxy;

(2) C 2-6 alkynyl optionally substituted by substituent(s) selected from hydroxy, optionally substituted amino, carboxy, sulfo group, phosphoric acid group and heterocyclyl;

(3) heterocyclyl group optionally substituted by substituent(s) selected from hydroxy and optionally substituted C 1-6 alkyl; or

(4) aryl C 1-6 alkyl substituted by substituent(s) selected from hydroxy, optionally substituted amino, carboxy, sulfo group, phosphoric acid group and heterocyclyl,

or a pharmaceutically acceptable salt thereof.

6. The compound according to claim 2 , wherein R 2 is

(1) C 1-6 alkyl optionally substituted by substituent(s) selected from hydroxy, optionally substituted C 1-6 alkoxy, optionally substituted C 1-6 alkylcarbonyloxy and monocyclic heterocyclylcarbonyloxy; or

(2) C 2-6 alkynyl optionally substituted by substituent(s) selected from optionally substituted amino and heterocyclyl; or

(3) heterocyclyl optionally substituted by optionally substituted C 1-6 alkyl,

or a pharmaceutically acceptable salt thereof.

7. The compound according to claim 2 , wherein R 1 is hydrogen, or a pharmaceutically acceptable salt thereof.

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

9. A method of treating cancer in a patient comprising administering to the patient the compound according to claim 2 or a pharmaceutically acceptable salt thereof.

10. A method of treating cancer, cancer metastasis and/or cancer recurrence in a patient, comprising administering to the patient the compound according to claim 2 or a pharmaceutically acceptable salt thereof.

11. The method according to claim 10 , wherein a cancer stem cell is contacted with the compound of formula (I) or a pharmaceutically acceptable salt thereof.

12. The method according to claim 9 , wherein a cancer stem cell is contacted with the compound of formula (I) or a pharmaceutically acceptable salt thereof.

13. The compound according to claim 1 , wherein the substituent group α consists of

halogen,

hydroxy,

optionally substituted amino,

carboxy,

C 1-6 alkoxycarbonyl,

sulfo group,

phosphoric acid group,

di C 1-6 alkyl phosphoric acid group,

cyano,

C 1-6 alkyl,

C 3-7 cycloalkyl,

C 1-6 alkoxy,

optionally substituted aryl,

optionally substituted aryloxy,

aryl C 1-6 alkoxy,

optionally substituted heterocyclyl,

optionally substituted C 1-6 alkylcarbonyl,

heterocyclylcarbonyl,

optionally substituted C 1-6 alkylcarbonyloxy,

optionally substituted C 3-7 cycloalkylcarbonyloxy,

monocyclic heterocyclylcarbonyloxy,

optionally substituted C 1-6 alkoxycarbonyloxy,

optionally substituted heterocyclyl C 1-6 alkoxycarbonyloxy,

C 3-7 cycloalkyloxycarbonyloxy,

heterocyclyloxycarbonyloxy,

optionally substituted heterocyclyloxy and

tri C 1-6 alkylammonio,

or a pharmaceutically acceptable salt thereof.

14. The compound according to claim 1 , wherein R 1 is hydrogen, or a pharmaceutically acceptable salt thereof.

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

16. A method of treating cancer in a patient comprising administering to the patient the compound according to claim 1 or a pharmaceutically acceptable salt thereof.

17. A method of treating cancer, cancer metastasis and/or cancer recurrence in a patient, comprising administering to the patient the compound according to claim 1 or a pharmaceutically acceptable salt thereof.

18. The method according to claim 17 , wherein a cancer stem cell is contacted with the compound of formula (IA) or a pharmaceutically acceptable salt thereof.

19. The method according to claim 16 , wherein a cancer stem cell is contacted with the compound of formula (IA) or a pharmaceutically acceptable salt thereof.