Imidazolidine derivatives

1. A compound represented by formula (I):

wherein, n is an integer selected from 1 to 20, Q is

A is cyano group, —COOR 3 , —CONR 3 R 4 , a C 1 -C 4 alkyl group which may be substituted by one or more halogen atoms, or a nitro group;

B is a hydrogen atom, a halogen atom, —OR 3 or a C 1 -C 4 alkyl group which may be substituted by one or more halogen atoms;

X 1 and X 2 are independently selected from O and S;

m is an integer selected from 0 to 3;

E is independently a C 1 -C 4 alkyl group;

R 1 and R 2 are independently selected from a hydrogen atom, a C 1 -C 6 alkyl group, and a C 1 -C 6 alkylcarbonyl group;

R 3 and R 4 are independently selected from a hydrogen atom and a C 1 -C 6 alkyl group;

with the proviso that when X 1 is O and X 2 is S, Q is not 4-cyano-3-trifluoromethylphenyl group,

or a pharmaceutically acceptable salt, or a prodrug thereof.

2. A compound according to claim 1 or a pharmaceutically acceptable salt, or a prodrug thereof, wherein A is trifluoromethyl group, cyano group, carboxy group, carbamoyl group, N-methylcarbamoyl group, N,N -dimethylcarbamoyl group, or nitro group.

3. A compound according to claim 1 or a pharmaceutically acceptable salt, or a prodrug thereof, wherein B is a hydrogen atom, trifluoromethyl group, methyl group, ethyl group, a chlorine atom or methoxy group.

4. A compound according to claim 1 or a pharmaceutically acceptable salt, or a prodrug thereof, wherein X 1 is O, and X 2 is O or S.

5. A compound according to claim 1 or a pharmaceutically acceptable salt, or a prodrug thereof, wherein n is an integer selected from 1 to 10.

6. A compound according to claim 1 or a pharmaceutically acceptable salt, or a prodrug thereof, wherein R 1 and R 2 are hydrogen atoms.

7. A compound according to claim 1 or a pharmaceutically acceptable salt, or a prodrug thereof, wherein at least one of R 1 and R 2 is a methyl group or acetyl group.

8. A compound according to claim 1 or a pharmaceutically acceptable salt, or a prodrug thereof, wherein R 3 and R 4 are each independently selected from a hydrogen atom and methyl group.

9. A compound according to claim 1 or a pharmaceutically acceptable salt, or a prodrug thereof, which are selected from the group consisting of:

3-[3-(3-chloro-4-cyanophenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl]propane-1-sulfonic acid amide;

3-[3-(4-cyano-3-methoxyphenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl]propane-1-sulfonic acid amide;

3-[3-(4-cyano-2-methyl-3-trifluoromethylphenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl]propane-1-sulfonic acid amide;

3-[3-(4-cyano-2-methyl-5-trifluoromethylphenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl]propane-1-sulfonic acid amide;

3-[3-(4-nitro-3-trifluoromethylphenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl]propane-1-sulfonic acid amide;

3-[3-(4-cyano-3-methylphenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl]propane-1-sulfonic acid amide;

3-[3-(4-cyano-3-ethylphenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl]propane-1-sulfonic acid amide;

3-[3-(3-methyl-4-nitrophenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl]propane-1-sulfonic acid amide;

3-[3-(4-trifluoromethylnaphth-1-yl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl]propane-1-sulfonic acid amide;

3-[3-(4-cyanophenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl]propane-1-sulfonic acid amide;

3-[3-(4-carboxyphenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl]propane-1-sulfonic acid amide;

3-[3-(4-aminocarbonylphenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl]propane-1-sulfonic acid amide;

3-[3-{4-(N,N-dimethylaminocarbonyl)phenyl}-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl]propane-1-sulfonic acid amide;

3-[3-(4-carboxy-3-trifluoromethylphenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl]propane-1-sulfonic acid amide;

3-[3-(4-aminocarbonyl-3-trifluoromethylphenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl]propane-1-sulfonic acid amide;

3-[3-{4-(N,N-dimethylaminocarbonyl)-3-trifluoromethylphenyl}-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl]propane-1-sulfonic acid amide;

3-[3-(4-cyanonaphth-1-yl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl]propane-1-sulfonic acid amide;

3-[3-(4-nitronaphth-1-yl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl]propane-1-sulfonic acid amide;

3-[3-(4-aminocarbonylnaphth-1-yl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl]propane-1-sulfonic acid amide;

3-[3-{4-(N,N-dimethylaminocarbonyl)naphth-1-yl}-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl]propane-1-sulfonic acid amide;

3-[3-(3-chloro-4-cyanophenyl)-5,5-dimethyl-2,4-dioxoimidazolidin-1-yl]propane-1-sulfonic acid amide;

3-[3-(4-cyano-3-methoxyphenyl)-5,5-dimethyl-2,4-dioxoimidazolidin-1-yl]propane-1-sulfonic acid amide;

3-[3-(4-cyano-2-methyl-3-trifluoromethylphenyl)-5,5-dimethyl-2,4-dioxoimidazolidin-1-yl]propane-1-sulfonic acid amide;

3-[3-(4-cyano-2-methyl-5-trifluoromethylphenyl)-5,5-dimethyl-2,4-dioxoimidazolidin-1-yl]propane-1-sulfonic acid amide;

N-methyl-3-[3-(3-chloro-4-cyanophenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl]propane-1-sulfonic acid amide;

4-[3-(3-chloro-4-cyanophenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl]butane-1-sulfonic acid amide;

5-[3-(3-chloro-4-cyanophenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl]pentane-1-sulfonic acid amide;

2-[3-(3-chloro-4-cyanophenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl]ethane-1-sulfonic acid amide;

2-[3-(3-chloro-4-cyanophenyl)-5,5-dimethyl-2,4-dioxoimidazolidin-1-yl]ethane-1-sulfonic acid amide; and

N-acetyl-3-[3-(3-chloro-4-cyanophenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl]propane-1-sulfonic acid amide.

10. A pharmaceutical composition which contains the compound according to claim 1 or a pharmaceutically acceptable salt, a prodrug thereof as an active ingredient.

11. A process for preparing a compound represented by formula (I):

wherein, Q, X 1 , X 2 , n, R 1 and R 2 are as described in claim 1 , comprising steps of:

reacting a compound represented by formula (II):

wherein n is an integer selected from integers of 1 to 20;

Ra and Rb are each independently selected from a C 1 -C 6 alkyl group substituted by one or more W 1 , a C 1 -C 6 alkylcarbonyl group which may be substituted by one or more W 1 , an arylcarbonyl group which may be substituted by one or more W 2 , a C 1 -C 6 alkoxycarbonyl group which may be substituted by one or more W 1 , an aryloxycarbonyl group which may be substituted by one or more W 2 , a C 1 -C 6 alkylaminocarbonyl group which may be substituted by one or more W 1 , a di(C 1 -C 6 alkyl)aminocarbonyl group which may be substituted by one or more W 1 , a C 1 -C 6 alkylsulfonyl group which may be substituted by one or more W 1 , and an arylsulfonyl group which may be substituted by one or more W 2 , and R 1 and R 2 ; or

Ra and Rb may be joined together to form a group ═CH—W 3 ;

W 1 is a C 1 -C 6 alkoxy group, a C 1 -C 6 alkylthio group, a C 1 -C 6 alkylsulfynyl group, a C 1 -C 6 alkylsulfonyl group, an aryl group which may be substituted by one or more W 2 , an aryloxy group which may be substituted by one or more W 2 , or a C 7 -C 14 aralkyloxy group which may be substituted by one or more W 2 ;

W 2 is a C 1 -C 6 alkyl group, a C 1 -C 6 alkoxy group, a C 1 -C 6 haloalkyl group, a halogen atom, cyano group, or nitro group;

W 3 is a C 1 -C 6 alkyl group, a C 1 -C 6 alkoxy group, a C 1 -C 6 alkylamino group, a di(C 1 -C 6 alkyl)amino group;

R 1 and R 2 are as defined in claim 1 ; and

Rc is a C 1 -C 6 alkyl group, with a compound represented by the following formula (IV):

Q-N═C═X 2 (IV)

wherein, Q and X 2 are as defined in claim 1 , to obtain a compound represented by formula (III):

wherein, Q, X 1 , X 2 , n, Ra and Rb are as described hereinbefore; and

a deprotection in cases where at least one of the groups Ra and Rb is other than R 1 and R 2 .

12. A compound represented by formula (III):

wherein, Q, X 1 , X 2 n, Ra and Rb are as defined in cm 11 .