Fused 1,3-dihydro-imidazole ring compounds

1. A compound represented by the formula (I), or a salt thereof,

[wherein,

T 1 is a piperazin-1-yl group, a 3-amino-piperidin-1-yl group, or a 3-methylamino-piperidin-1-yl group;

X 3 denotes an oxygen atom or a sulfur atom,

X 1 denotes a C 1-6 alkyl group which may have substitutents, a C 2-6 alkenyl group which may have substitutents, a C 2-6 alkynyl group which may have substitutents, a C 6-10 aryl group which may have substitutents, a 5 to 10-membered heteroaryl group which may have substitutents, a C 6-10 aryl C 1-6 alkyl group which may have substitutents, or a 5 to 10-membered heteroaryl C 1-6 alkyl group which may have substitutents;

Z 1 denotes a nitrogen atom;

Z 2 denotes a group of the formula —CR 1 — and Z 3 denotes a nitrogen atom;

in formula (I), the following formula

denotes a double bond;

R 1 and X 2 each independently denote a hydrogen atom, a 4 to 8-membered heterocyclic group which may have substitutents, or a group represented by the formula —A 0 —A 1 —A 2 ;

A 0 denotes a single bond, or a C 1-6 alkylene group that may have 1 to 3 substituents selected from the following substituent group A;

A 1 denotes a single bond, oxygen atom, sulfur atom, a sulfinyl group, a sulfonyl group, a carbonyl group, a group of the formula —O—CO, a group of the formula —CO—O—, a group of the formula —NR A —, a group of the formula —CO—NR A —, a group of the formula NR A —CO—, a group of the formula —SO 2 —NR A —, or a group of the formula —NR A —SO 2 —;

A 2 and R A each independently denote a hydrogen atom, a cyano group, a C 1-6 alkyl group, a C 3-8 cycloalkyl group, a C 2-6 alkenyl group, a C 2-6 alkynyl group, a C 6-10 aryl group, a 5 to 10-membered heteroaryl group, a 4 to 8-membered heterocyclic group, or a C 6-10 aryl C 1-6 alkyl group;

however, A 2 and R A each independently may have 1 to 3 substituents selected from the substituent group A described below:

<Substituent group A>

substituent group A refers to a group consisting of: a hydroxyl group, a mercapto group, a cyano group, a halogen atom, a C 1-6 alkyl group, a C 3-8 cycloalkyl group, a C 2-6 alkenyl group, a C 2-6 alkynyl group, a C 6-10 aryl group, a 5 to 10-membered heteroaryl group, a 4 to 8-membered heterocyclic group, a C 1-6 alkoxy group, a C 1-6 alkylthio group, a group of the formula —NR B4 —R B5 (where R B4 and R B5 denote hydrogen atoms or C 1-6 alkyl groups), a group of the formula —CO—R B6 (where R B6 denotes a 1-pyrrolidinyl group, a 1-morpholinyl group, a 1-piperazinyl group, or a 1-piperidyl group), and a group of the formula —CO—R B —R B2 (where R B denotes a single bond, an oxygen atom, or a group represented by the formula —NR B3 —; R B2 and R B3 each independently denote a hydrogen atom, a C 1-6 alkyl group, a C 3-8 cycloalkyl group, a C 2-6 alkenyl group, a C 2-6 alkynyl group, a C 6-10 aryl group, a 5 to 10-membered heteroaryl group, a C 6-10 aryl C 1-6 alkyl group, or a 5 to 10-membered heteroaryl C 1-6 alkyl group)].

2. A compound represented by the formula (II), or a salt thereof,

[wherein,

Z 3a denotes a nitrogen atom;

X 3a denotes an oxygen atom or a sulfur atom;

T 1a is a piperazin-1-yl group, a 3-amino-piperidin-1-yl group, or a 3-methylamino-piperidin-1-yl group;

X 1a denotes a hydrogen atom, a C 2-6 alkenyl group, a C 2-6 alkynyl group, or a benzyl group;

R 1a denotes a hydrogen atom, a halogen atom, a C 1-6 alkyl group, a cyano group, or a group represented by the formula —A 0a —A 1a ;

A 0a denotes an oxygen atom, a sulfur atom, or a group represented by the formula —NA 2a ;

A 1a denotes a hydrogen atom, a C 1-6 alkyl group, a C 2-6 alkenyl group, a C 2-6 alkynyl group, a phenyl group, a cyanophenyl group, a carbamoylphenyl group, a benzyl group, a pyridylmethyl group, or a pyridyl group;

A 2a denotes a hydrogen atom, or a C 1-6 alkyl group;

X 2a denotes a hydrogen atom, a C 2-6 alkenyl group, a C 2-6 alkynyl group, a cyclohexenyl group, a 1H-pyridin-2-on-yl group, a 1-methyl-1H-pyridin-2-on-yl group, a C 1-6 alkyl group that may have a group selected from substituent group B described below, a phenyl group that may have a group selected from substituent group B described below, a 5 or 6-membered heteroaryl group that may have a group selected from substituent group B described below, a phenyl C 1-6 alkyl group that may have a group selected from substituent group B described below, or a pyridyl C 1-6 alkyl group that may have a group selected from substituent group B described below:

<Substituent group B>

substituent group B refers to a group consisting of a chlorine atom, a bromine atom, a cyano group, a C 1-6 alkyl group, a C 2-6 alkenyl group, a C 2-6 alkynyl group, a C 3-8 cycloalkyl group, a C 1-6 alkoxy group, a carbamoyl group, a carboxyl group, and a C 1-6 alkoxycarbonyl group].

3. A compound represented by the formula (III), or a salt thereof,

[wherein,

T 1b stands for a piperazin-1-yl group, a 3-amino-piperidin-1-yl group, or a 3-methylamino-piperidin-1-yl group;

X 1b denotes a 2-pentynyl group, a 2-butynyl group, a 3-methyl-2-butenyl group, a 2-butenyl group, or a benzyl group; and

R 1a and X 2a have the same meaning as R 1a and X 2a of claim 2 defined above].

4. The compound of claim 2 or 3 , or a salt thereof, wherein R 1a is a hydrogen atom, a chlorine atom, a cyano group, a methoxy group, an ethoxy group, an i-propyloxy group, a methylthio group, an allyloxy group, a 2-butynyloxy group, a phenyloxy group, a cyanophenyloxy group, a carbamoylphenyloxy group, a phenylmethyloxy group, a (phenylmethyl)amino group, a pyridylmethyloxy group, a pyridyloxy group, an amino group, a methylamino group, a dimethylamino group, or a diethylamino group.

5. The compound of claim 2 or 3 , or a salt thereof, wherein R 1a is a hydrogen atom, a methoxy group, an ethoxy group, an i-propyloxy group, a 2-cyanophenyloxy group, or a 2-carbamoylphenyloxy group.

6. The compound of claim 2 or 3 , or a salt or a hydrate thereof, wherein X 2a is a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, a 2-methylpropyl group, a group represented by the formula —CH 2 —R 10 (where R 10 denotes a carbamoyl group, a carboxyl group, a methoxycarbonyl group, a cyano group, a cyclopropyl group, or a methoxy group), a 3-cyanopropyl group, an allyl group, a 2-propionyl group, a 2-butynyl group, a 2-methyl-2-propenyl group, a 2-cyclohexynyl group, a chloropyridyl group, a methoxypyridyl group, a methoxypyrimidyl group, a pyridyl group, a furyl group, a thienyl group, a pyridylmethyl group, a 1H-pyridin-2-on-5-yl group, a 1-methyl-1H-pyridin-2-on-5-yl group, a phenyl group that may have a group selected from substituent group Y described below, a benzyl group that may have a group selected from substituent group Y described below, or a phenethyl group that may have a group selected from substituent group Y described below:

substituent group Y is a group consisting of: a chlorine atom, a bromine atom, a methoxy group, a cyano group, a vinyl group, and a methyl group.

7. The compound of claim 2 or 3 , or a salt thereof, wherein X 2a is a methyl group, n-propyl group, allyl group, 2-propynyl group, 2-butynyl group, cyclopropylmethyl group, phenyl group, 3-pyridyl group, 3-furyl group, 3-thienyl group, 2-methoxy-5-pyrimidinyl group, 2-methoxy-5-pyridyl group, 2-chloro-4-pyridyl group, or 1H-pyridin-2-on-5-yl group.

8. A pharmaceutical composition comprising the compound of claim 1 , or a salt thereof, and an adjuvant for formulation.