MEDICAMENT FOR TREATMENT OF MULTIPLE SCLEROSIS

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TECHNICAL FIELD

The present invention relates to a medicament for preventive and/or therapeutic treatment of multiple sclerosis.

BACKGROUND ART

Multiple sclerosis (MS) is an inflammatory demyelinating disease of the central nerves, and is characterized by central nerve lesions frequently occurring spatially and temporally. It is the most frequently occurring disease among neurological disorders that affect young adults in Europe and America, where the prevalence rate per population of 100,000 is around 50, and the number of persons with this disease in Japan is estimated to be about 13,000 as a whole (about 8 or 9 persons per population of 100,000). It cannot be said that causes of the onset of this disease have fully been elucidated, although genetic factors, environmental factors, virus infection, and the like have been suggested, and it is a designated intractable disease authorized as a specified disease in Japan. It is characterized by long affection period with repeating recurrence and remission, inflammation and disruption of myelin due to autoimmunity, and dyscrasia of the optic nerve or spine due to damages to nerve fibers, and as the symptoms, although they vary depending on parts and times of demyelination, there are caused sensation abnormalities (numbness, abnormalities of thermal sensation, migraine, trigeminal neuralgia, itching, etc. (European Journal of Pain, 9, pp. 531-542, 2005; Pain, 127, pp. 35-41, 2007; International Review of Neurobiology, 79, pp. 303-321, 2007)), and motor dysfunctions.

Although pregabalin, tricyclic antidepressants, antiepileptics, and narcotic analgesics are used for central pain of multiple sclerosis patients, the effect of such symptomatic therapies for pains is considered restrictive at present (Practice of Pain Management, 5, pp. 88-90, 2014). It has been reported that, in experimental autoimmune encephalomyelitis (EAE) model animals, which is an animal model of multiple sclerosis, pain symptoms such as hyperalgesia and allodynia accompany, like clinical cases (Pain, 110, pp. 560-570, 2004: Pain, 141, pp. 156-164, 2009). It has been reported that the analgesic action of morphine markedly decreases in allodynia observed in the EAE model. It has also been pointed out that glia cells are activated in the brain and spine of EAE model rats, and this may be involved in advance of the pathological conditions and demyelination (Brain: A Journal of Neurology, 125. pp. 1462-1473, 2002; Brain Pathology (Zurich, Switzerland), 18, pp. 86-95, 2008).

By the way, the ATP receptors are broadly classified into the P2X family of the ion channel type receptors, and the P2Y family of the G protein coupling type receptors, and the P2X4 receptor (Genebank No. X87763), a subtype of the P2X family, has been reported to be widely expressed in the central nervous system, and the like (EMBO J., 15, pp. 55-62, 1996; J. Neurosci., 16, pp. 448-455, 1996; FEBS Lett., 375, pp. 129-133, 1995; Proc. Natl. Acad. Sci. USA. 93, pp. 3684-3788, 1996; Biochem. Res., Commun., 220. pp. 196-202, 1996). Recently, Inoue et al. verified the involvement of the P2X receptor in neurogenic pain by using a spinal nerve-damaged animal model in which allodynia can be detected, and they reported that nerve-damaged type unusual pain (especially allodynia) is induced through the P2X4 receptor expressed in the microglia cells of the spinal cord (Nature, 424, pp. 778-783, 2003; Nature, 438, pp. 1017-1021, 2005; U.S. Patent Published Application No. 2005/74819).

Guo et al. (Neuroscience, 134, pp. 199-205, 2005) elucidated that the P2X4 receptors existing in the circumference of blood vessels of the spine or brain markedly increase with advance of the pathological symptoms in the EAE model, marked increase of the expression is also observed not only in the circumference of blood vessels, but also in tissue parenchyma, and P2X4 receptor-positive cells expressed in the parenchyma exist mainly on infiltrating macrophages by double staining, and reported the relation of the P2X4 receptors and the pathology Nuria et al. reported that expression of the P2X4 receptors is accelerated and P2X4 receptor-positive cells increase in the spine of EAE rat and optic nerve of multiple sclerosis patients (Glia, 62, pp. 171-184, 2014). Although Nakata reported an analgesic action of NCP-308, a P2X4 receptor antagonist, for a neuropathic pain by using an EAE model animal, the chemical structure of that substance has not been clarified (Kyushu University. Graduate School of Pharmaceutical Sciences, Department of Molecular and System Pharmacology, doctoral thesis. March, 2013).

As compounds having a P2X4 receptor antagonist activity, there are known benzofuro-1,4-diazepin-2-one derivatives (WO2004/085440), and naphthodiazepinedione derivatives (WO2010/093061, WO2012/008478. WO2012/14910, WO2012/17876. WO2013/105608, WO2015/005468, WO2015/005467, etc.). WO2008/020651, WO2007/049825, WO2015/088564, and WO2015/088565 also disclose compounds having a P2X4 receptor antagonist activity, and although they suggest effectiveness of the compounds on pain of multiple sclerosis as general descriptions, they do not disclose any verification data obtained by using EAE model animals.

PRIOR ART REFERENCES
Patent Documents

Patent document 1: U.S. Patent Published Application No. 2005/074819

Patent document 2: WO2004/085440

Patent document 3: WO2010/093061

Patent document 4: WO2012/008478

Patent document 5: WO2012/014910

Patent document 6: WO2012/017876

Patent document 7: WO2013/105608

Patent document 8: WO2015/005468

Patent document 9: WO2015/005467

Patent document 10: WO2008/020651

Patent document 11: WO2007/049825

Patent document 12: WO2015/088564

Patent document 13: WO2015/088565

Non-Patent Documents

Non-patent document 1: European Journal of Pain (London, England), 9. pp. 531-542, 2005

Non-patent document 2: Pain, 127, pp. 35-41, 2007

Non-patent document 3: International Review of Neurobiology, 79. pp. 303-321, 2007

Non-patent document 4: Practice of Pain Management, 5, pp. 88-90, 2014

Non-patent document 5: Pain, 110. pp. 560-570, 2004

Non-patent document 6: Pain, 141, pp. 156-164, 2009

Non-patent document 7: Brain: A Journal of Neurology, 125, pp. 1462-1473, 2002

Non-patent document 8: Brain Pathology (Zurich, Switzerland), 18, pp. 86-95, 2008

Non-patent document 9: ENBO J., 15, pp. 55-62, 1996

Non-patent document 10: J. Neurosci., 16, pp. 448-455, 1996 Non-patent document 11: FEBS Lett., 375, pp. 129-133, 1995

Non-patent document 12: Proc. Natl. Acad. Sci. USA, 93, pp. 3684-3788, 1996

Non-patent document 13: Biochem. Res. Commun., 220, pp. 196-202, 1996

Non-patent document 14: Nature, 424, pp. 778-783, 2003

Non-patent document 15: Nature, 438, pp. 1017-1021, 2005

Non-patent document 16: Neuroscience, 134, pp. 199-205, 2005

Non-patent document 17: Glia, 62, pp. 171-184, 2014

Non-patent document 18: Kyushu University, Graduate School of Pharmaceutical Sciences, Department of Molecular and System Pharmacology, doctoral thesis of Eriko Nakata, March, 2013

SUMMARY OF THE INVENTION
Object to be Achieved by the Invention

An object of the present invention is to provide a medicament for preventive and/or therapeutic treatment of multiple sclerosis.

Amore preferred object of the present invention is to provide a medicament for preventive and/or therapeutic treatment of a pain such as neuropathic pain accompanying multiple sclerosis, especially a medicament for preventive and/or therapeutic treatment of a convalescent pain accompanying multiple sclerosis.

Means for Achieving the Object

The inventors of the present invention conducted various researches in order to achieve the aforementioned object, as a result, found that naphthodiazepinedione derivatives having a P2X4 receptor antagonist activity are highly effective for preventive and/or therapeutic treatment of neuropathic pain accompanying multiple sclerosis, and accomplished the present invention.

The present invention thus provides a medicament for preventive and/or therapeutic treatment of multiple sclerosis, which contains a compound having a P2X4 receptor antagonist activity, or a salt thereof, or a hydrate or solvate thereof as an active ingredient.

As the compound having a P2X4 receptor antagonist activity, for example, the compounds represented by the following general formulas (IA) to (IG) can be used.

More preferably, as the compound having a P2X4 receptor antagonist activity, the compounds represented by the following general formula (IH) can be used.

The medicament of the present invention can be used for, for example, preventive and/or therapeutic treatment of a pain, preferably a neurogenic pain, accompanying multiple sclerosis, and can be more preferably used for preventive and/or therapeutic treatment of a convalescent neurogenic pain accompanying multiple sclerosis.

As other aspects of the present invention, there are provided use of a compound having a P2X4 receptor antagonist activity or a salt thereof, or a hydrate or solvate thereof for manufacture of the aforementioned medicament; and a method for preventive and/or therapeutic treatment of multiple sclerosis, preferably a pain accompanying multiple sclerosis, more preferably a neurogenic pain accompanying multiple sclerosis, particularly preferably a convalescent neurogenic pain accompanying multiple sclerosis, which comprises the step of administering a preventively and/or therapeutically effective amount of a compound having a P2X4 receptor antagonist activity or a salt thereof, or a hydrate or solvate thereof to a mammal including human.

Effect of the Invention

The medicament of the present invention is useful as a medicament for preventive and/or therapeutic treatment of multiple sclerosis, and can exhibit high effectiveness in preventive and/or therapeutic treatment of a neuropathic pain accompanying multiple sclerosis, especially a convalescent pain accompanying multiple sclerosis.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 is a graph showing the results of observation of daily basis change of P2X4 expression performed in Example 2 by calculating P2X4/GAPDH ratios, and ratio of the ratios (EAE model group/control group).

FIG. 2 shows results of the immunohistological staining performed in Example 3. A: P2X4 receptor staining image of the posterior horn of spinal cord in an EAE model rat on Day 7, B: P2X4 receptor staining image of the posterior horn of spinal cord in the EAE model rat on Day 14, C: P2X4 receptor staining image of the posterior horn of spinal cord in the EAE model rat on Day 21, D: P2X4 receptor staining image of the posterior horn of spinal cord in the EAE model rat on Day 28. E: Iba1 (red) and P2X4 receptor (green) staining image of the posterior horn of spinal cord in the EAE model rat on Day 28, and F: P2X4 receptor staining image of the posterior horn of spinal cord in a control rat on Day 28.

FIG. 3 shows influences of preventive administration of the compound A to an EAE model rat on the pain threshold observed in Example 4. The gray backgrounds indicate the administration periods. ∘: Adjuvant+medium (n=8). •: gpMBP(68-84)-adjuvant+medium (n=7 or 8), ▴: gpMBP(68-84)-adjuvant+compound A (n=5 to 8).

FIG. 4 shows influences of preventive administration of the compound A to an EAE model rat on the pain threshold observed in Example 5. The gray backgrounds indicate the administration periods. ∘: Adjuvant+medium (n=8), •: Adjuvant+medium (n=6), Δ: gpMBP(68-84)-adjuvant+medium (n=7 to 11), ▴: gpMBP(68-84)-adjuvant+compound A (n=7 to 11).

FIG. 5 shows influences of preventive continuous administration of the compound B to an EAE model rat on the pain threshold observed in Example 6. The gray backgrounds indicate the administration periods. ∘: Adjuvant+medium (n=7 or 8), •: gpMBP(68-84)-adjuvant+medium (n=2 to 6), ▴: gpMBP(68-84)-adjuvant+compound B (n=3 to 6).

MODES FOR CARRYING OUT THE INVENTION

As the active ingredient of the medicament of the present invention, the compounds represented by the general formulas (IA) to (IH) shown below can be used. The abbreviations used in the tables mentioned below, and the like are as follows. Me: methyl group. Et: ethyl group, Pr: n-propyl group, iPr: isopropyl group, tBu: tert-butyl group, Ac: acetyl group, Ph: phenyl group.

(A-1) A compound represented by the following general formula (IA):

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wherein, in the formula, R^1Arepresents hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, or an alkyl group having 1 to 3 carbon atoms and substituted with phenyl group,

R^2Aand R^3Amay be the same or different, and represent hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, an acylamino group having 2 to 8 carbon atoms, an acylamino group having 2 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkylsulfonylamino group having 1 to 8 carbon atoms, carboxyl group, an acyl group having 2 to 8 carbon atoms, an alkoxycarbonyl group (the alkoxy moiety thereof has 1 to 8 carbon atoms), carbamoyl group, an alkylthio group having 1 to 8 carbon atoms, an alkylsulfinyl group having 1 to 8 carbon atoms, an alkylsulfonyl group having 1 to 8 carbon atoms, or sulfamoyl group.

R^4Aand R^5Amay be the same or different, and represent hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, or an alkyl group having 1 to 3 carbon atoms and substituted with phenyl group, and

W^Arepresents a 5- or 6-membered heterocyclic ring which contains 1 to 4 nitrogen atoms as ring-constituting elements, and may have a substituent.

As for the general formula (IA), examples of the alkyl group having 1 to 8 carbon atoms as R^1A, R^2A, R^3A, R^4A, and R^5Ainclude methyl group, ethyl group, propyl group, isopropyl group, butyl group, i-butyl group, t-butyl group, pentyl group, hexyl group, and the like.

Examples of the alkenyl group having 2 to 8 carbon atoms as R^1Ainclude allyl group, and the like.

Examples of the alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms as R^1A, R^2A, R^3A, R^4A, and R^5Ainclude methyl group, ethyl group, propyl group, isopropyl group, butyl group, or t-butyl group, and the like substituted with 1 to 3 halogen atoms such as fluorine atom, chlorine atom, and bromine atom, and preferred examples of the same include trifluoromethyl group, chloromethyl group, 2-chloroethyl group, 2-bromoethyl group, 2-fluoroethyl group, and the like.

Examples of the alkyl group having 1 to 3 carbon atoms and substituted with phenyl group as R^1A, R^4A, and R^5Ainclude benzyl group, and the like.

Examples of the alkoxy group having 1 to 8 carbon atoms as R^2Aand R^3Ainclude methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, i-butoxy group, t-butoxy group, pentyloxy group, hexyloxy group, and the like.

Examples of the alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms as R^2Aand R^3Ainclude methyl group ethyl group, propyl group, isopropyl group, butyl group, or t-butyl group, and the like substituted with 1 to 3 halogen atoms such as fluorine atom, chlorine atom, and bromine atom, and preferred examples of the same include trifluoromethoxy group, 2-chloroethoxy group, 2-bromoethoxy group, 2-fluoroethoxy group, and the like.

Examples of the halogen atom as R^2Aand R^3Ainclude fluorine atom, chlorine atom, bromine atom, and the like.

Examples of the alkylamino group having 1 to 8 carbon atoms as R^2Aand R^3Ainclude methylamino group, ethylamino group, and the like.

Examples of the dialkylamino group having 1 to 8 carbon atoms as R^2Aand R^3Ainclude dimethylamino group, diethylamino group, and the like.

Examples of the acylamino group having 2 to 8 carbon atoms as R^2Aand R^3Ainclude acetylamino group.

Examples of the acylamino group having 2 to 8 carbon atoms and substituted with 1 to 3 halogen atoms as R^2Aand R^3Ainclude trifluoromethylcarbonylamino group.

Examples of the alkylsulfonylamino group having 1 to 8 carbon atoms as R^2Aand R^3Ainclude methylsulfonylamino group.

Examples of the acyl group having 2 to 8 carbon atoms as R^2Aand R^3Ainclude acetyl group.

Examples of the alkoxycarbonyl group (the alkoxy moiety thereof has 1 to 8 carbon atoms) as R^2Aand R^3Ainclude methoxycarbonyl group, ethoxycarbonyl group, and the like.

Examples of the alkylthio group having 1 to 8 carbon atoms as R^2Aand R^3Ainclude methylthio group.

Examples of the alkylsulfinyl group having 1 to 8 carbon atoms as R^2Aand R^3Ainclude methylsulfinyl group.

Examples of the alkylsulfonyl group having 1 to 8 carbon atoms as R^2Aand R^3Ainclude methylsulfonyl group.

Examples of the 5- or 6-membered heterocyclic ring which contains 1 to 4 nitrogen atoms as ring-constituting elements, and may have a substituent, as W^Ainclude tetrazole, 1,2,4-triazole, 1,2,3-triazole, 1,2,4-oxadiazole, pyrazole, imidazole, oxazole, isoxazole, pyrrole, thiazole, pyridine, and pyrrolidine.

Examples of the substituent which the 5- or 6-membered heterocyclic ring which contains 1 to 4 nitrogen atoms as ring-constituting elements, and may have a substituent, as W^Amay have include an alkyl group having 1 to 8 carbon atoms such as methyl group and ethyl group, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms such as trifluoromethyl group, a halogen atom such as fluorine atom, cyano group, oxo group, thioxo group, and the like.

In the general formula (IA), 1 to 3 of the same or different R^2Aand R^3Amay exist on the benzene rings on which R^2Aand R^3Asubstitute.

As the compounds of the general formula (IA), the following compounds are preferred.

(A-2) The compound according to (A-1), wherein W^Ais tetrazole, 1,2,4-triazole, 1,2,3-triazole, 1,2,4-oxadiazole, pyrazole, or imidazole which may have a substituent selected from an alkyl group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, cyano group, oxo group, and thioxo group.

(A-3) The compound according to (A-1) or (A-2), wherein W^Ais tetrazole, 1,2,4-triazole, or 1,2,3-triazole which may have a substituent selected from an alkyl group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, and cyano group.

(A-4) The compound according to any one of (A-1) to (A-3), wherein W^Ais 5-oxo-1,2,4-oxadiazole, or 5-thioxo-1,2,4-oxadiazole.

(A-5) The compound according to any one of (A-1) to (A-3), wherein W^Ais tetrazole.

A diazepinedione derivative of the aforementioned general formula (IA), or a pharmacologically acceptable salt thereof.

(A-6) The compound according to any one of (A-1) to (A-5), wherein R^1Ais hydrogen atom, or an alkyl group having 1 to 8 carbon atoms.

(A-7) The compound according to any one of (A-1) to (A-6), wherein R^1Ais hydrogen atom.

(A-8) The compound according to any one of (A-1) to (A-7), wherein R^4Ais hydrogen atom, and R^5Ais hydrogen atom, or an alkyl group having 1 to 8 carbon atoms.

(A-9) The compound according to any one of (A-1) to (A-8), wherein both R^4Aand R^5Aare hydrogen atoms.

(A-10) The compound according to any one of (A-1) to (A-9), wherein R^2Ais hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, carboxyl group, an acyl group having 2 to 8 carbon atoms, or an alkoxycarbonyl group (the alkoxy moiety thereof has 1 to 8 carbon atoms).

(A-11) The compound according to any one of (A-1) to (A-10), wherein R^2Ais hydrogen atom.

(A-12) The compound according to any one of (A-1) to (A-11), wherein R^3Ais hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, carboxyl group, an acyl group having 2 to 8 carbon atoms, or an alkoxycarbonyl group (the alkoxy moiety thereof has 1 to 8 carbon atoms).

(A-13) The compound according to any one of (A-1) to (A-12), wherein R^3Ais hydrogen atom.

Typical compounds falling within the scope of the general formula (IA) are mentioned below.

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(In the formula, R^2Aand R^3Arepresent hydrogen atom, and R^1A, R^4A, R^5A, and W^Aas well as the substitution position of W^Aare as shown in Tables 1 to 3)

TABLE 1

Substitution

position of

R^1A
W^A
W^A
R^4A/R^5A

H
2-
1H-Tetrazol-5-yl
H/H

H
3-
1H-Tetrazol-5-yl
H/H

H
3-
(1-Methyl-1H-tetrazol)-5-yl
H/H

H
4-
1H-Tetrazol-5-yl
H/H

Me
3-
1H-Tetrazol-5-yl
H/H

Me
3-
1H-Tetrazol-5-yl
Me/H

Bn
3-
1H-Tetrazol-5-yl
H/H

H
3-
1H-Tetrazol-1-yl
H/H

H
3-
1H-Tetrazol-1-yl
Me/Me

H
3-
(1,2,3-Triazol)-5-yl
H/H

H
3-
(1,2,4-Triazol)-3-yl
H/H

H
4-
(1,2,4-Triazol)-3-yl
H/H

TABLE 2

Substitution

position of

R^1A
W^A
W^A
R^4A/R^5A

H
2-
(1,2,4-Triazol)-1-yl
H/H

H
3-
(1,2,4-Triazol)-1-yl
H/H

H
3-
[5-(Trifluoromethyl)-1,2,4-
H/H

triazol]-3-yl

H
3-
[5-(Trifluoromethyl)-1,2,4-
Et/H

triazol]-3-yl

H
3-
[5-Fluoro-1,2,3-triazol]-4-yl
H/H

H
3-
[5-Fluoro-1,2,3-triazol]-4-yl
Me/Me

H
3-
[5-Cyano-1,2,3-triazol]-4-yl
H/H

H
4-
1H-Imidazol-1-yl
H/H

H
4-
1H-Imidazol-1-yl
Pr/H

H
3-
1H-Imidazol-2-yl
H/H

H
3-
1H-Imidazol-4-yl
H/H

H
3-
Imidazolin-2-yl
H/H

TABLE 3

Substitution

position of

R^1A
W^A
W^A
R^4A/R^5A

H
2-
Pyrazol-3-yl
H/H

H
3-
Pyrazol-4-yl
H/H

H
3-
Pyrazol-5-yl
Me/H

H
3-
(1,2,4-Oxadiazol)-3-yl
H/H

H
3-
(1,3,4-Oxadiazol)-2-yl
H/H

H
3-
(5-Oxo-1,2,4-oxadiazol)-3-yl
H/H

H
3-
Pyrrol-1-yl
H/H

H
4-
Pyrrolidin-2-yl
H/H

Me
4-
Pyrrolidin-2-yl
Me/H

H
4-
(1,3-Oxazol)-5-yl
H/H

H
3-
(1,3-Oxazol)-5-yl
H/H

H
2-
(1,3-Thiazol)-5-yl
H/H

“Intentionally Left Blank”
<Typical Compound IA-2>

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(In the formula, R^1A, R^2A, R^4A, R^5A, and W^Aas well as the substitution position of W^Aare as shown in Table 4.)

TABLE 4

Substitution

position of

R^4A/

R^1A
R^2A
W^A
W^A
R^5A

H
4-OH
3-
1H-Tetrazol-5-yl
H/H

H
4-OMe
3-
1H-Tetrazol-5-yl
H/H

Me
2-Cl
3-
1H-Tetrazol-5-yl
H/H

H
2,6-Cl
3-
1H-Tetrazol-5-yl
H/H

H
4-F
3-
1H-Tetrazol-5-yl
H/H

H
4-Br
3-
1H-Tetrazol-5-yl
Et/H

H
3-OMe
4-
(1-Methyl-1H-tetrazol)-
H/H

5-yl

H
4-Me
3-
1H-Tetrazol-5-yl
H/H

H
4-Cl
3-
(1,2,3-Triazol)-5-yl
Me/H

H
4-CF₃
3-
(1,2,3-Triazol)-5-yl
H/H

H
3-SMe
4-
(1,2,4-Triazol)-1-yl
H/H

H
3-SO₂Me
4-
1H-Imidazol-1-yl
H/H

H
3-NHSO₂Me
4-
1H-Imidazol-1-yl
H/H

H
4-OMe
3-
1H-Imidazol-4-yl
H/H

H
4-F
2-
Pyrazol-3-yl
H/H

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(In the formula, R^1A, R^2A, R^3A, R^4A, R^5A, and W as well as the substitution position of W^Aare as shown in Tables 5 and 6.)

TABLE 5

Substitution

position of

R^4A/

R^1A
R^2A
W^A
W^A
R^3A
R^5A

H
H
3-
1H-Tetrazol-5-yl
9-Br
H/H

H
4-OMe
3-
1H-Tetrazol-5-yl
9-Cl
H/H

H
4-OH
3-
1H-Tetrazol-5-yl
10-OMe
H/H

H
2-Cl
3-
1H-Tetrazol-5-yl
9-Br
H/H

H
2,6-Cl
3-
1H-Tetrazol-5-yl
9-Me
H/H

H
H
3-
1H-Tetrazol-5-yl
10-Cl
Me/H

H
3-OMe
4-
(1-Methyl-1H-
9-CF₃
H/H

tetrazol)-5-yl

TABLE 6

Substitution

position of

R^4A/

R^1A
R^2A
W^A
W^A
R^3A
R^5A

H
4-Me
3-
1H-Tetrazol-1-yl
9-CN
Pr/H

Me
H
3-
(1,2,3-Triazol)-5-yl
9-OH
H/H

Et
H
3-
(1,2,3-Triazol)-5-yl
10-F
H/H

H
3-Br
4-
(1,2,4-Triazol)-1-yl
9-SMe
H/H

Allyl
H
4-
1H-Imidazol-1-yl
8-OMe
H/H

H
H
3-
1H-Imidazol-1-yl
10-OMe
Me/Me

(B-1) A compound represented by the following general formula (IB):

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wherein, in the formula, R^1Band R^2Bmay be the same or different, and represent hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, an acylamino group having 2 to 8 carbon atoms, an acylamino group having 2 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkylsulfonylamino group having 1 to 8 carbon atoms, carboxyl group, an acyl group having 2 to 8 carbon atoms, an alkoxycarbonyl group (the alkoxy moiety thereof has 1 to 8 carbon atoms), carbamoyl group, an alkylthio group having 1 to 8 carbon atoms, an alkylsulfinyl group having 1 to 8 carbon atoms, an alkylsulfonyl group having 1 to 8 carbon atoms, or sulfamoyl group.

R^3Brepresents hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, or an alkyl group having 1 to 3 carbon atoms and substituted with phenyl group,

R^4Band R^5Bmay be the same or different, and represent hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, or an alkyl group having 1 to 3 carbon atoms and substituted with phenyl group,

R^6Brepresents hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, an acylamino group having 2 to 8 carbon atoms, an acylamino group having 2 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkylsulfonylamino group having 1 to 8 carbon atoms, carboxyl group, an acyl group having 2 to 8 carbon atoms, an alkoxycarbonyl group (the alkoxy moiety thereof has 1 to 8 carbon atoms), carbamoyl group, an alkylthio group having 1 to 8 carbon atoms, an alkylsulfinyl group having 1 to 8 carbon atoms, an alkylsulfonyl group having 1 to 8 carbon atoms, sulfamoyl group, a phenyl group which may have a substituent, or a heterocyclic group which may have a substituent,

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represents a 5- to 8-membered non-aromatic ring, which may contain 1 or 2 heteroatoms selected from N. S, and O as ring-constituting elements, and condenses at the 1- and 2-positions of the benzene ring.

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represents an aromatic ring selected from benzene ring, naphthalene ring, thiophene ring, pyridine ring, pyrimidine ring, indole ring, indazole ring, benzotriazole ring, benzisoxazole ring, benzimidazole ring, and quinoline ring,

Z^Brepresents O or S.

when X^Bis N, Y^Brepresents C═O or C═S, and the double line consisting of the solid line and the broken line represents a single bond, and

when X^Bis C, Y^Brepresents N, and the double line consisting of the solid line and the wavy line represents a double bond.

(B-2) A compound represented by the following general formula (IIB):

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wherein, in the formula, R^11Band R^12Bmay be the same or different, and represent hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, an acylamino group having 2 to 8 carbon atoms, an acylamino group having 2 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkylsulfonylamino group having 1 to 8 carbon atoms, carboxyl group, an acyl group having 2 to 8 carbon atoms, an alkoxycarbonyl group (the alkoxy moiety thereof has 1 to 8 carbon atoms), carbamoyl group, an alkylthio group having 1 to 8 carbon atoms, an alkylsulfinyl group having 1 to 8 carbon atoms, an alkylsulfonyl group having 1 to 8 carbon atoms, or sulfamoyl group.

R^13Brepresents hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, or an alkyl group having 1 to 3 carbon atoms and substituted with phenyl group,

R^14Band R^15Bmay be the same or different, and represent hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, or an alkyl group having 1 to 3 carbon atoms and substituted with phenyl group.

R^16Brepresents hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, an acylamino group having 2 to 8 carbon atoms, an acylamino group having 2 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkylsulfonylamino group having 1 to 8 carbon atoms, carboxyl group, an acyl group having 2 to 8 carbon atoms, an alkoxycarbonyl group (the alkoxy moiety thereof has 1 to 8 carbon atoms), carbamoyl group, an alkylthio group having 1 to 8 carbon atoms, an alkylsulfinyl group having 1 to 8 carbon atoms, an alkylsulfonyl group having 1 to 8 carbon atoms, sulfamoyl group, a phenyl group which may have a substituent, or a heterocyclic group which may have a substituent.

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represents a 5- to 8-membered non-aromatic ring which may contain 1 or 2 heteroatoms selected from N, S, and O as ring-constituting elements, and condenses at the 1- and 2-positions of the benzene ring,

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Z^1Band Z^2Bmay be the same or different, and represent O or S.

(B-3) A compound represented by the following general formula (IIIB).

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wherein, in the formula, R^21Band R^22Bmay be the same or different, and represent hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, an acylamino group having 2 to 8 carbon atoms, an acylamino group having 2 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkylsulfonylamino group having 1 to 8 carbon atoms, carboxyl group, an acyl group having 2 to 8 carbon atoms, an alkoxycarbonyl group (the alkoxy moiety thereof has 1 to 8 carbon atoms), carbamoyl group, an alkylthio group having 1 to 8 carbon atoms, an alkylsulfinyl group having 1 to 8 carbon atoms, an alkylsulfonyl group having 1 to 8 carbon atoms, or sulfamoyl group,

R^23Brepresents hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, or an alkyl group having 1 to 3 carbon atoms and substituted with phenyl group.

R^24Band R^25B, may be the same or different, and represent hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, or an alkyl group having 1 to 3 carbon atoms and substituted with phenyl group.

R^26Brepresents hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, an acylamino group having 2 to 8 carbon atoms, an acylamino group having 2 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkylsulfonylamino group having 1 to 8 carbon atoms, carboxyl group, an acyl group having 2 to 8 carbon atoms, an alkoxycarbonyl group (the alkoxy moiety thereof has 1 to 8 carbon atoms), carbamoyl group, an alkylthio group having 1 to 8 carbon atoms, an alkylsulfinyl group having 1 to 8 carbon atoms, an alkylsulfonyl group having 1 to 8 carbon atoms, sulfamoyl group, a phenyl group which may have a substituent, or a heterocyclic group which may have a substituent, and

p^Brepresents 0 or 1.

As for the aforementioned general formulas (IB), (IIB), and (IIIB), examples of the alkyl group having 1 to 8 carbon atoms as R^1B, R^2B, R^3B, R^4B, R^5B, and R^6Binclude methyl group, ethyl group, propyl group, isopropyl group, butyl group, i-butyl group, t-butyl group, pentyl group, hexyl group, and the like.

Examples of the alkenyl group having 2 to 8 carbon atoms as R^1B, R^2B, R^3B, and R^6Binclude allyl group, and the like.

Examples of the alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms as R^1B, R^2B, R^3B, R^4B, R^5B, and R^6Binclude methyl group, ethyl group, propyl group, isopropyl group, butyl group, and t-butyl group substituted with 1 to 3 halogen atoms such as fluorine atom, chlorine atom, and bromine atom, and the like, and preferred examples of the same include trifluoromethyl group, chloromethyl group, 2-chloroethyl group, 2-bromoethyl group, 2-fluoroethyl group, and the like.

Examples of the alkyl group having 1 to 3 carbon atoms and substituted with phenyl group as R^3B, R^4B, and R^5Binclude benzyl group, and the like.

Examples of the alkoxy group having 1 to 8 carbon atoms as R^1B, R^2B, and R^6Binclude methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, i-butoxy group, t-butoxy group, pentyloxy group, hexyloxy group, and the like.

Examples of the alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms as R^1B, R^2B, and R^3Binclude methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, t-butoxy group substituted with 1 to 3 halogen atoms such as fluorine atom, chlorine atom, and bromine atom, and the like, and preferred examples of the same include trifluoromethoxy group, chloromethoxy group, 2-chloroethoxy group, 2-bromoethoxy group, 2-fluoroethoxy group, and the like.

Examples of the halogen atom as R^1B, R^2B, R^4B, R^5B, and R^6Binclude fluorine atom, chlorine atom, bromine atom, and the like.

Examples of the alkylamino group having 1 to 8 carbon atoms as R^1B, R^2B, and R^6Binclude methylamino group, ethylamino group, and the like.

Examples of the dialkylamino group having 2 to 8 carbon atoms as R^1B, R^2R, and R^6Binclude dimethylamino group, diethylamino group, and the like.

Examples of the acylamino group having 2 to 8 carbon atoms as R^1B, R^2B, and R^6Binclude acetylamino group.

Examples of the acylamino group having 2 to 8 carbon atoms and substituted with 1 to 3 halogen atoms as R^1B, R^2B, and R include trifluoromethylcarbonylamino group.

Examples of the alkylsulfonylamino group having 1 to 8 carbon atoms as R^1B, R^2B, and R^6Binclude methylsulfonylamino group.

Examples of the acyl group having 2 to 8 carbon atoms as R^1B, R^2B, and R^6Binclude acetyl group.

Examples of the alkoxycarbonyl group (the alkoxy moiety thereof has 1 to 8 carbon atoms) as R^1B, R^2B, and R^6Binclude methoxycarbonyl group, ethoxycarbonyl group, and the like.

Examples of the alkylthio group having 1 to 8 carbon atoms as R^1B, R^2B, and R^6Binclude methylthio group.

Examples of the alkylsulfinyl group having 1 to 8 carbon atoms as R^1B, R^2B, and R^6Binclude methylsulfinyl group.

Examples of the alkylsulfonyl group having 1 to 8 carbon atoms as R^1B, R^2B, and R^6Binclude methylsulfonyl group.

Preferred examples of the substituent of the phenyl group which may have a substituent as R^6Binclude an alkyl group having 1 to 8 carbon atoms such as methyl group and ethyl group, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms such as trifluoromethyl group, a halogen atom such as fluorine atom, cyano group, and the like.

Preferred examples of the heterocyclic group of the heterocyclic group which may have a substituent, as R^6Binclude tetrazolyl group, triazolyl group, pyridyl group, imidazolyl group, oxazolyl group, thiazolyl group, and the like, and it may also be oxadiazole group.

Preferred examples of the substituent of the heterocyclic ring which may have a substituent as R^6Binclude an alkyl group having 1 to 8 carbon atoms such as methyl group and ethyl group, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms such as trifluoromethyl group, a halogen atom such as fluorine atom, cyano group, oxo, and the like, and it may also be phenyl group.

Examples of

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include tetrahydronaphthalene, indane, indoline, tetrahydroquinoline, tetrahydroisoquinoline, and the like.

In the aforementioned general formula (IB), a plurality of the same or different R^1B, R^2B, and R^6Bmay exist on the rings on which R^1B, R^2B, and R^6Bsubstitute.

As for R^11Bto R^16Bin the aforementioned general formula (IIB), and R^21Bto R^26Bin the aforementioned general formula (IIIB), examples of the alkyl group having 1 to 8 carbon atoms, alkenyl group having 2 to 8 carbon atoms, alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, alkyl group having 1 to 3 carbon atoms and substituted with phenyl group, alkoxy group having 1 to 8 carbon atoms, alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, halogen atom, alkylamino group having 1 to 8 carbon atoms, dialkylamino group having 1 to 8 carbon atoms, acylamino group having 2 to 8 carbon atoms, acylamino group having 2 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, alkylsulfonylamino group having 1 to 8 carbon atoms, acyl group having 2 to 8 carbon atoms, alkoxycarbonyl group (the alkoxy moiety thereof has 1 to 8 carbon atoms), alkylthio group having 1 to 8 carbon atoms, alkylsulfinyl group having 1 to 8 carbon atoms, alkylsulfonyl group having 1 to 8 carbon atoms, phenyl group which may have a substituent, heterocyclic group which may have a substituent, and the like include those similar to the examples mentioned above for R^1Bto R^6Bin the general formula (IB).

Similarly, as for the heterocyclic group which may have a substituent as R^16Bin the general formula (IIB), and R^26Bin the general formula (IIIB), examples of the alkyl group having 1 to 8 carbon atoms, alkoxy group having 1 to 8 carbon atoms, alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, halogen atom, alkylamino group having 1 to 8 carbon atoms, and dialkylamino group having 2 to 8 carbon atoms as the substituent include those mentioned above for R^1Bto R^6Bin the general formula (IB).

Examples of

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include tetrahydronaphthalene, indane, indoline, tetrahydroquinoline, tetrahydroisoquinoline, and the like.

In the aforementioned general formula (IIB), a plurality of the same or different R^11B, R^12B, and R^16Bmay exist on the rings on which R^11B, R^12B, and R^16Bsubstitute.

In the aforementioned general formula (IIIB), a plurality of the same or different R^21B, R^22B, and R^26Bmay exist on the rings on which R^21B, R^22B, and R^26Bsubstitute.

As compounds falling within the scope of the aforementioned general formula (IIB), the following compounds are preferred.

(B-2-1) The compound according to (B-2), wherein R^11Bis hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, amino group, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, or an acylamino group having 2 to 8 carbon atoms.

(B-2-2) The compound according to (B-2) or (B-2-1), wherein R^12Bis hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, an acylamino group having 2 to 8 carbon atoms, or an acylamino group having 2 to 8 carbon atoms and substituted with 1 to 3 halogen atoms.

(B-2-3) The compound according to (B-2), or any one of (B-2-1) and (B-2-2), wherein R^13Bis hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms.

(B-2-4) The compound according to (B-2), or any one of (B-2-1) to (B-2-3), wherein R^14Band R^15Bmay be the same or different, and are hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms.

(B-2-5) The compound according to (B-2), or any one of (B-2-1) to (B-2-4), wherein R^16Bis hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, or a heterocyclic group which may have a substituent.

(B-2-6) The compound according to (B-2), or any one of (B-2-1) to (B-2-5), wherein R^16Bis a tetrazolyl group, triazolyl group, pyridyl group, pyrazolyl group, oxadiazolyl group, isoxazolyl group, pyrrolyl group, pyrrolidinyl group, imidazolyl group, oxazolyl group, or thiazolyl group which may have a substituent selected from an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, and a dialkylamino group having 2 to 8 carbon atoms.

(B-2-7) The compound according to (B-2), or any one of (B-2-1) to (B-2-6), wherein R^16Bis a tetrazolyl group, triazolyl group, pyridyl group, imidazolyl group, oxazolyl group, or thiazolyl group which may have a substituent selected from an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, cyano group, and amino group.

(B-2-8) The compound according to (B-2), or any one of (B-2-1) to (B-2-7), wherein

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is tetrahydronaphthalene, indane, indoline, tetrahydroquinoline, or tetrahydroisoquinoline.

(B-2-9) The compound according to (B-2), or any one of (B-2-1) to (B-2-8), wherein

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is a benzene ring.

(B-2-10) The compound according to (B-2), or any one of (B-2-1) to (B-2-9), wherein both Z^1Band Z^2Bare 0.

As the compounds of the general formula (IIIB), the compounds mentioned below are preferred.

(B-3-1) The compound according to (B-3), wherein R^21Bis hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, amino group, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, or an acylamino group having 2 to 8 carbon atoms.

(B-3-2) The compound according to (B-3) or (B-3-1), wherein R^22Bis hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, an acylamino group having 2 to 8 carbon atoms, or an acylamino group having 2 to 8 carbon atoms and substituted with 1 to 3 halogen atoms.

(B-3-3) The compound according to (B-3). (B-3-1), or (B-3-2), wherein R^23Bis hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms.

(B-3-4) The compound according to (B-3), or any one of (B-3-1) to (B-3-3), wherein R^24B, and R^25Bmay be the same or different, and are hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms.

(B-3-5) The compound according to (B-3), or any one of (B-3-1) to (B-3-4), wherein R^26Bis hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, or a heterocyclic group which may have a substituent.

(B-3-6) The compound according to (B-3), or any one of (B-3-1) to (B-3-5), wherein R^26Bis a tetrazolyl group, triazolyl group, pyridyl group, pyrazolyl group, oxadiazolyl group, isoxazolyl group, pyrrolyl group, pyrrolidinyl group, imidazolyl group, oxazolyl group, or thiazolyl group which may have a substituent selected from an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, and a dialkylamino group having 2 to 8 carbon atoms.

(B-3-7) The compound according to (B-3), or any one of (B-3-1) to (B-3-6), wherein R^26Bis a tetrazolyl group, triazolyl group, pyridyl group, imidazolyl group, oxazolyl group, or thiazolyl group which may have a substituent selected from an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, cyano group, and amino group.

R^3Bin the general formula (IB). R^13Bin the general formula (IIB), and R^23Bin the general formula (IIIB) may be an acyl group having 2 to 8 carbon atoms such as acetyl.

R^6Bin the general formula (TB), R^16Bin the general formula (IIB), and R^26Bin the general formula (IIIB) may be an alkoxycarbonylamino group having 3 to 8 carbon atoms such as tert-butoxycarbonylamino group.

Further,

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in the general formula (IB), and

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in the general formula (IIB) may be 2,3-dihydrobenzo[1,4]dioxine.

Typical compounds falling within the scope of the general formula (IB) are mentioned below.

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(In the formula, A^B-B^B-D^B-E^B, R^23B, R^24B/R^25B, and R^26Bare as shown in Tables 7 to 9.)

TABLE 7

R^24B/

A^B-B^B-D^B-E^B
R^23B
R^25B
R^26B

CH₂CH₂CH₂CH₂
H
H/H
3-CN

CH₂CH₂CH₂CH₂
H
H/H
3-OH

CH₂CH₂CH₂CH₂
H
H/H
3-CO₂H

CH₂CH₂CH₂CH₂
H
H/H
3-CONH₂

C(CH₃)₂CH₂CH₂CH₂
H
H/H
3,4-OMe

CH₂C(CH₃)₂CH₂CH₂
Me
H/H
3,4-OMe

CH₂CH₂C(CH₃)₂CH₂
Et
H/H
3-OH, 4-F

CH₂CH₂CH₂CH₂
H
H/H
3-NH₂

NHCH₂CH₂CH₂
H
H/H
3-NHMe

NMeCH₂CH₂CH₂
H
H/H
3-CF₃

OCH₂CH₂O
H
H/H
3-NHCH₂CF₃

OCH₂CH₂O
Me
H/H
2-OH, 3-OH

C(CH₃)₂CH₂CH₂C(CH₃)₂
Et
H/H
3,4,5-Me

TABLE 8

R^24B/

A^B-B^B-D^B-E^B
R^23B
R^25B
R^26B

CH₂CH₂CH₂CH₂
H
Me/H
4-OH

CH₂CH₂CH₂CH₂
H
Me/Me
4-NH₂

CH₂CH₂CH₂CH₂
H
Pr/H
4-NO₂

C(CH₃)₂CH₂CH₂CH₂
H
H/H
4-CN

CH₂C(CH₃)₂CH₂CH₂
Me
CF₃/H
4-Ph

CH₂CH₂C(CH₃)₂CH₂
Et
H/H
4-CH₂OH

CH₂CH₂CH₂CH₂
H
H/H
3-CH₂OH

NHCH₂CH₂CH₂
H
H/H
3-Ac

NMeCH₂CH₂CH₂
H
H/H
3,5-OMe

OCH₂CH₂O
H
H/H
3-OH, 4-NH₂

OCH₂CH₂O
Me
H/H
3-CH₂NH₂

C(CH₃)₂CH₂CH₂C(CH₃)₂
Et
H/H
3-SO₂CH₃

CH₂CH₂CH₂CH₂
H
Me/H
3-iPr

CH₂CH₂CH₂CH₂
H
Me/H
3-NMe₂

TABLE 9

R^24B/

A^B-B^B-D^B-E^B
R^23B
R^25B
R^26B

CH₂CH₂CH₂CH₂
H
Me/H
3-Ac

C(CH₃)₂CH₂CH₂CH₂
H
Pr/H
3,4-NH₂

CH₂C(CH₃)₂CH₂CH₂
H
H/H
NHMe

CH₂CH₂C(CH₃)₂CH₂
Et
H/H
3-NHCH₂CF₃

CH₂CH₂CH₂CH₂
H
H/H
3-NHAc

NHCH₂CH₂CH₂
H
H/H
3-SO₂Me

NMeCH₂CH₂CH₂
H
H/H
4-Me

OCH₂CH₂O
H
H/H
4-iPr

OCH₂CH₂O
Me
H/H
3-Ph

C(CH₃)₂CH₂CH₂C(CH₃)₂
Et
H/H
3-F, 4-OH

CH₂CH₂CH₂CH₂
Ac
H/H
3-F, 4-OMe

CH₂CH₂CH₂CH₂
H
Me/H
4-NHEt

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(In the formula, A^B-B^B-D^B-E^B, R^24B/R^25B, R^26B, and R^27Bare as shown in Tables 10 to 12, and “Position” in the tables means the substitution position of R^26B.)

TABLE 10

R^24B/

A^B-B^B-D^B-E^B
R^25B
Position
R^26B
R^27B

CH₂CH₂CH₂CH₂
H/H
3
1H-Tetrazol-5-yl
H

C(CH₃)₂CH₂CH₂CH₂
H/H
3
1H-Tetrazol-5-yl
H

C(CH₃)₂CH₂CH₂CH₂
H/H
3
1H-Tetrazol-1-yl
4-F

C(CH₃)₂CH₂CH₂C(CH₃)₂
H/H
3
2-Methyl-2H-tetrazol-5-yl
3-F

CH₂CH₂C(CH₃)₂CH₂
H/H
3
1,2,3-Triazol-5-yl
2-F

CH₂CH₂CH₂CH₂
H/H
3
1,2,4-Triazol-3-yl
H

NHCH₂CH₂CH₂
H/H
3
5-(Trifluoromethyl)-1,2,4-triazol-3-yl
H

NMeCH₂CH₂CH₂
H/H
4
1H-Imidazol-1-yl
H

OCH₂CH₂O
H/H
4
1H-Imidazol-2-yl
H

OCH₂CH₂O
H/H
3
5-Cyano-1H-1,2,3-triazol-4-yl
H

C(CH₃)₂CH₂CH₂C(CH₃)₂
H/H
3
1-Methyl-1H-tetrazol-5-yl
H

CH₂CH₂CH₂CH₂
Me/H
3
Pyrazol-3-yl
4-OH

CH₂CH₂CH₂CH₂
Me/Me
3
Pyrazol-4-yl
H

TABLE 11

R^24B/

A^B-B^B-D^B-E^B
R^25B
Position
R^26B
R^27B

C(CH₃)₂CH₂CH₂CH₂
H/H
3
5-Oxo-1,2,4-oxadiazol-3-yl
4-NH₂

CH₂C(CH₃)₂CH₂CH₂
CF₃/H
3
1,2,4-Oxadiazol-3-yl
H

CH₂CH₂C(CH₃)₂CH₂
H/H
3
1,3,4-Oxadiazol-2-yl
4-F

CH₂CH₂CH₂CH₂
H/H
4
Pyrrol-1-yl
3-F

NHCH₂CH₂CH₂
H/H
4
Pyrrolidin-2-yl
H

NMeCH₂CH₂CH₂
H/H
2
1,3-Oxazol-5-yl
H

OCH₂CH₂O
H/H
3
1,3-Thiazol-5-yl
H

OCH₂CH₂O
H/H
3
5-(Trifluoromethyl)-1H-imidazol-2-yl
H

C(CH₃)₂CH₂CH₂C(CH₃)₂
H/H
3
5-Chloro-1H-imidazol-2-yl
4-OH

TABLE 12

R^24B/

A^B-B^B-D^B-E^B
R^25B
Position
R^26B
R^27B

CH₂CH₂CH₂CH₂
Me/H
4
5-Methyl-1H-imidazol-2-y
4-NH₂

CH₂CH₂CH₂CH₂
Me/H
4
5-Amino-1H-imidazol-2-y
3-F

CH₂CH₂CH₂CH₂
Me/H
3
2-Ethyl-2H-tetrazol-5-yl
H

C(CH₃)₂CH₂CH₂CH₂
Pr/H
3
2-(2,2,2-Trifluoroethyl)-2H-tetrazol-5-yl
2,6-F

CH₂C(CH₃)₂CH₂CH₂
H/H
3
1,3-Oxazol-2-yl
H

CH₂CH₂C(CH₃)₂CH₂
H/H
3
1,3-Thiazol-2-yl
H

CH₂CH₂CH₂CH₂
H/H
4
3,5-Dimethylisoxazol-4-yl
H

NH₂CH₂CH₂NH
H/H
3
3-Methyl-1,2,4-oxadiazol-5-yl
H

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(In the formula. A^B-B^B-D^B-E^B, R^24B/R^25B, and T^0Bare as shown in Tables 13 to 15.)

TABLE 13

R^24B/

A^B-B^B-D^B-E^B
R^25B
T^0B

CH₂CH₂CH₂CH₂
H/H
Pyrimidin-2-yl

C(CH₃)₂CH₂CH₂CH₂
H/H
Pyrimidin-5-yl

CH₂C(CH₃)₂CH₂CH₂
H/H
Pyridin-2-yl

CH₂CH₂C(CH₃)₂CH₂
H/H
Pyridin-3-yl

CH₂CH₂CH₂CH₂
H/H
Pyridin-4-yl

NHCH₂CH₂CH₂
Me/H
Thiophen-2-yl

NMeCH₂CH₂CH₂
H/H
Thiophen-3-yl

OCH₂CH₂O
H/H
Thiophen-3-yl

OCH₂CH₂O
H/H
5-Hydroxypyridin-3-yl

C(CH₃)₂CH₂CH₂C(CH₃)₂
H/H
5-Methoxypyridin-3-yl

CH₂CH₂CH₂CH₂

F/H
5-Aminopyridin-3-yl

CH₂CH₂CH₂CH₂
Me/Me
5-Chloropyridin-3-yl

CH₂CH₂CH₂CH₂
Pr/H
6-Chloropyridin-3-yl

TABLE 14

R^24B/

A^B-B^B-D^B-E^B
R^25B
T^0B

CH₂CH₂CH₂CH₂
Pr/H
6-Chloropyridin-3-yl

CH₂CH₂CH₂CH₂
H/H
1H-Indazol-6-yl

C(CH₃)₂CH₂CH₂CH₂
H/H
1H-Indazol-5-yl

CH₂C(CH₃)₂CH₂CH₂
H/H
1H-Indazol-4-yl

CH₂CH₂C(CH₃)₂CH₂
H/H
1H-Benzotriazol-6-yl

C(CH₃)₂CH₂CH₂CH₂
H/H
1H-Benzotriazol-4-yl

CH₂CH₂CH₂CH₂
H/H
1H-Benzimidazol-6-yl

CH₂C(CH₃)₂CH₂CH₂
H/H
1H-Indazol-4-yl

CH₂CH₂C(CH₃)₂CH₂
H/H
1H-Indol-6-yl

C(CH₃)₂CH₂CH₂CH₂
H/H
1H-Indol-5-yl

C(CH₃)₂CH₂CH₂CH₂
H/H
1H-Indol-4-yl

CH₂C(CH₃)₂CH₂CH₂
H/H
Benzisoxazol-6-yl

C(CH₃)₂CH₂CH₂CH₂
H/H
1H-Benzimidazol-5-yl

TABLE 15

R^24B/

A^B-B^B-D^B-E^B
R^25B
T^0B

C(CH₃)₂CH₂CH₂CH₂
H/H
1H-Benzimidazol-6-yl

CH₂C(CH₃)₂CH₂CH₂
H/H
2-(Trifluoromethyl)-

1H-benzimidazol-5-yl

CH₂CH₂CH₂CH₂
H/H
Quinolin-5-yl

C(CH₃)₂CH₂CH₂CH₂
H/H
Quinolin-8-yl

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(In the formula, A^B-B^B-D^B, R^23B, R^24B/R^25B, and R^26Bare as shown in Tables 16 to 18.)

TABLE 16

R^24B/

A^B-B^B-D^B
R^23B
R^25B
R^26B

CH₂CH₂CH₂
H
H/H
3-CN

CH₂CH₂CH₂
H
H/H
3-OH

CH₂CH₂CH₂
H
H/H
3-CO₂H

CH₂CH₂CH₂
H
H/H
3-CONH₂

OCH₂O
H
H/H
3,4-OMe

OCH₂O
Me
H/H
3,4-OMe

OCH₂O
Et
H/H
3-OH, 4-F

OCH₂O
H
H/H
3-NH₂

CH₂CH₂CH₂
H
H/H
3-NHMe

CH₂CH₂CH₂
H
H/H
3-CF₃

CH₂CH₂CH₂
H
H/H
3-NHCH₂CF₃

CH₂CH₂CH₂
Me
H/H
2-OH, 3-OH

OCH₂O
Et
H/H
3,4,5-Me

TABLE 17

R^24B/

A^B-B^B-D^B
R^23B
R^25B
R^26B

OCH₂O
H
Me/H
4-OH

OCH₂O
H
Me/Me
4-NH₂

OCH₂O
H
Pr/H
4-NO₂

CH₂CH₂CH₂
H
H/H
4-CN

CH₂CH₂CH₂
Me
CF₃/H
4-Ph

CH₂CH₂CH₂
Et
H/H
4-CH₂OH

OCH₂O
H
H/H
3-CH₂OH

CH₂CH₂CH₂
H
H/H
3-Ac

CH₂CH₂CH₂
H
H/H
3,5-OMe

CH₂CH₂CH₂
H
H/H
3-OH, 4-NH₂

OCH₂O
Me
H/H
3-CH₂NH₂

CH₂CH₂CH₂
Et
H/H
3-SO₂CH₃

CH₂CH₂CH₂
H
Me/H
3-iPr

CH₂CH₂CH₂
H
Me/H
3-NMe₂

OCH₂O
H
Me/H
3-Ac

CH₂CH₂CH₂
H
Pr/H
3,4-NH₂

TABLE 18

R^24B/

A^B-B^B-D^B
R^23B
R^25B
R^26B

CH₂CH₂CH₂
H
H/H
NHMe

CH₂CH₂CH₂
Et
H/H
3-NHCH₂CF₃

OCH₂O
H
H/H
3-NHAc

CH₂CH₂CH₂
H
H/H
3-SO₂Me

CH₂CH₂CH₂
H
H/H
4-Me

CH₂CH₂CH₂
H
H/H
4-iPr

OCH₂O
Me
H/H
3-Ph

CH₂CH₂CH₂
Et
H/H
3-F, 4-OH

CH₂CH₂CH₂
Ac
H/H
3-F, 4-OMe

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(In the formula. A^B-B^B-D^B, R^24B/R^25B, R^26B, and R^27Bare as shown in Tables 19 to 21, and “Position” in the tables means the substitution positions of R^26B.)

TABLE 19

R^24B/

A^B-B^B-D^B
R^25B
Position
R^26B
R^27B

CH₂CH₂CH₂
H/H
3
1H-Tetrazol-5-yl
H

CH₂CH₂CH₂
H/H
4
1H-Tetrazol-5-yl
H

CH₂CH₂CH₂
H/H
3
1H-Tetrazol-1-yl
H

CH₂CH₂CH₂
H/H
3
2-Methyl-2H-
H

tetrazol-5-yl

OCH₂O
H/H
3
1,2,3-Triazol-5-yl
2-F

OCH₂O
H/H
3
1,2,4-Triazol-3-yl
H

OCH₂O
H/H
3
5-(Trifluoromethyl)-
H

1,2,4-triazol-3-yl

OCH₂O
H/H
4
1H-Imidazol-1-yl
H

CH₂CH₂CH₂
H/H
4
1H-Imidazol-2-y
H

CH₂CH₂CH₂
H/H
3
5-Cyano-1H-1,2,3-
H

triazol-4-yl

CH₂CH₂CH₂
H/H
3
1-Methyl-1H-
H

tetrazol-5-yl

CH₂CH₂CH₂
Me/H
3
Pyrazol-3-yl
4-OH

TABLE 20

R^24B/

A^B-B^B-D^B
R^25B
Position
R^26B
R^27B

OCH₂O
Me/Me
3
Pyrazol-4-yl
H

OCH₂O
H/H
3
5-Oxo-1,2,4-oxadiazol-3-yl
4-NH₂

OCH₂O
CF₃/H
3
1,2,4-Oxadiazol-3-yl
H

CH₂CH₂CH₂
H/H
3
1,3,4-Oxadiazol-2-yl
4-F

CH₂CH₂CH₂
H/H
4
Pyrrol-1-yl
3-F

CH₂CH₂CH₂
H/H
4
Pyrrolidin-2-yl
H

OCH₂O
H/H
2
1,3-Oxazol-5-yl
H

CH₂CH₂CH₂
H/H
3
1,3-Thiazol-5-yl
H

CH₂CH₂CH₂
H/H
3
5-(Trifluoromethyl)-
H

1H-imidazol-2-y

CH₂CH₂CH₂
H/H
3
5-Chloro-1H-imidazol-2-y
4-OH

OCH₂O
Me/H
4
5-Methyl-1H-imidazol-2-y
4-NH₂

CH₂CH₂CH₂
Me/H
4
5-Amino-1H-imidazol-2-y
3-F

TABLE 21

R^24B/

A^B-B^B-D^B
R^25B
Position
R^26B
R^27B

CH₂CH₂CH₂
Me/H
3
2-Ethyl-2H-tetrazol-5-yl
H

CH₂CH₂CH₂
Pr/H
3
2-(2,2,2-Trifluoroethyl)-
2,6-F

2H-tetrazol-5-yl

OCH₂O
H/H
3
1,3-Oxazol-2-yl
H

CH₂CH₂CH₂
H/H
3
1,3-Thiazol-2-yl
H

CH₂CH₂CH₂
H/H
4
3,5-Dimethylisoxazol-4-yl
H

CH₂CH₂CH₂
H/H
3
3-Methyl-1,2,4-oxadiazol-5-yl
H

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(In the formula, A^B-B^B-D^B, R^24B/R^25B, and T^0Bare as shown in Tables 22 to 24.)

TABLE 22

A^B-B^B-D^B
R^24B/R^25B
T^0B

CH₂CH₂CH₂
H/H
Pyrimidin-2-yl

CH₂CH₂CH₂
H/H
Pyrimidin-5-yl

CH₂CH₂CH₂
H/H
Pyridin-2-yl

CH₂CH₂CH₂
H/H
Quinolin-2-yl

CH₂CH₂CH₂
H/H
Quinolin-3-yl

CH₂CH₂CH₂
H/H
Pyridin-3-yl

OCH₂O
H/H
Pyridin-4-yl

OCH₂O
Me/H
Thiophen-2-yl

OCH₂O
H/H
Thiophen-3-yl

OCH₂O
H/H
Thiophen-3-yl

CH₂CH₂CH₂
H/H
5-Hydroxypyridin-3-yl

CH₂CH₂CH₂
H/H
5-Methoxypyridin-3-yl

NHCH₂CH₂
F/H
5-Aminopyridin-3-yl

TABLE 23

A^B-B^B-D^B
R^24B/R^25B
T^0B

CH₂CH₂CH₂
Me/Me
5-Chloropyridin-3-yl

OCH₂O
Pr/H
6-Chloropyridin-3-yl

OCH₂O
Pr/H
6-Chloropyridin-3-yl

OCH₂O
H/H
1H-Indazol-6-yl

OCH₂O
H/H
1H-Indazol-5-yl

CH₂CH₂CH₂
H/H
1H-Indazol-4-yl

CH₂CH₂CH₂
H/H
1H-Benzotriazol-6-yl

CH₂CH₂CH₂
H/H
1H-Benzotriazol-4-yl

OCH₂O
H/H
1H-Benzimidazol-6-yl

CH₂CH₂CH₂
H/H
1H-Indazol-4-yl

CH₂CH₂CH₂
H/H
1H-Indol-6-yl

TABLE 24

A^B-B^B-D^B
R^24B/R^25B
T^0B

NHCH₂CH₂
H/H
1H-Indol-5-yl

OCH₂O
H/H
1H-Indol-4-yl

CH₂CH₂CH₂
H/H
Benzisoxazol-6-yl

CH₂CH₂CH₂
H/H
1H-Benzimidazol-5-yl

CH₂CH₂CH₂
H/H
1H-Benzimidazol-6-yl

OCH₂O
H/H
2-Trifluoromethyl-1H-benzimidazol-5-yl

CH₂CH₂CH₂
H/H
Quinolin-5-yl

CH₂CH₂CH₂
H/H
Quinolin-8-yl

(C-1) A compound represented by the following general formula (IC):

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wherein, in the formula, R^1Cand R^2Cmay be the same or different, and represent hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an aralkyl group (the aryl moiety thereof has 6 to 10 carbon atoms, and the alkylene moiety thereof has 1 to 3 carbon atoms), a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, an acylamino group having 2 to 8 carbon atoms, an acylamino group having 2 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkylsulfonylamino group having 1 to 8 carbon atoms, carboxyl group, an acyl group having 2 to 8 carbon atoms, an alkoxycarbonyl group (the alkoxy moiety thereof has 1 to 8 carbon atoms), carbamoyl group, an alkylthio group having 1 to 8 carbon atoms, an alkylsulfinyl group having 1 to 8 carbon atoms, an alkylsulfonyl group having 1 to 8 carbon atoms, or sulfamoyl group,

R^3Crepresents hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, or an aralkyl group (the aryl moiety thereof has (to 10 carbon atoms, and the alkylene moiety thereof has 1 to 3 carbon atoms).

R^4Crepresents hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an aralkyl group (the aryl moiety thereof has 6 to 10 carbon atoms, and the alkylene moiety thereof has 1 to 3 carbon atoms), an alkyl group having 1 to 8 carbon atoms and substituted with hydroxyl group, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, an alkylamino group having 1 to 5 carbon atoms and substituted with 1 to 5 halogen atoms, a dialkylamino group having 2 to 8 carbon atoms, an acylamino group having 2 to 8 carbon atoms, an acylamino group having 2 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkylsulfonylamino group having 1 to 8 carbon atoms, a benzenesulfonylamino group which may have a substituent, carboxyl group, an acyl group having 2 to 8 carbon atoms, an alkoxycarbonyl group (the alkoxy moiety thereof has 1 to 8 carbon atoms), carbamoyl group, an alkylthio group having 1 to 8 carbon atoms, an alkylsulfinyl group having 1 to 8 carbon atoms, an alkylsulfonyl group having 1 to 8 carbon atoms, sulfamoyl group, a phenyl group which may have a substituent, or a heterocyclic group which may have a substituent,

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represents a 5- to 8-membered ring which condenses at the 1- and 2-positions of the benzene ring, and may contain a heteroatom selected from N, S, and O as a ring-constituting element and

embedded image

represents an aromatic ring selected from benzene ring, naphthalene ring, pyridine ring, pyrimidine ring, quinoline ring, indole ring, indoline ring, benzimidazole ring, indazole ring, benzisoxazole ring, and benztriazole ring.

(C-2) A compound represented by the following general formula (IIC):

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wherein, in the formula, R^11Cand R^12Cmay be the same or different, and represent hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an aralkyl group (the aryl moiety thereof has 6 to 10 carbon atoms, and the alkylene moiety thereof has 1 to 3 carbon atoms), a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, an acylamino group having 2 to 8 carbon atoms, an acylamino group having 2 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkylsulfonylamino group having 1 to 8 carbon atoms, carboxyl group, an acyl group having 2 to 8 carbon atoms, an alkoxycarbonyl group (the alkoxy moiety thereof has 1 to 8 carbon atoms), carbamoyl group, an alkylthio group having 1 to 8 carbon atoms, an alkylsulfinyl group having 1 to 8 carbon atoms, an alkylsulfonyl group having 1 to 8 carbon atoms, or sulfamoyl group.

R^13Crepresents hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, or an aralkyl group (the aryl moiety thereof has 6 to 10 carbon atoms, and the alkylene moiety thereof has 1 to 3 carbon atoms),

R^14Crepresents hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an aralkyl group (the aryl moiety thereof has 6 to 10 carbon atoms, and the alkylene moiety thereof has 1 to 3 carbon atoms), an alkyl group having 1 to 8 carbon atoms and substituted with hydroxyl group, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, an alkylamino group having 1 to 5 carbon atoms and substituted with 1 to 5 halogen atoms, a dialkylamino group having 2 to 8 carbon atoms, an acylamino group having 2 to 8 carbon atoms, an acylamino group having 2 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkylsulfonylamino group having 1 to 8 carbon atoms, a benzenesulfonylamino group which may have a substituent, carboxyl group, an acyl group having 2 to 8 carbon atoms, an alkoxycarbonyl group (the alkoxy moiety thereof has 1 to 8 carbon atoms), carbamoyl group, an alkylthio group having 1 to 8 carbon atoms, an alkylsulfinyl group having 1 to 8 carbon atoms, an alkylsulfonyl group having 1 to 8 carbon atoms, sulfamoyl group, a phenyl group which may have a substituent, or a heterocyclic group which may have a substituent, and

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represents naphthalene ring, tetrahydronaphthalene ring, or indane ring.

As for the general formulas (IC) and (IIC), examples of the alkyl group having 1 to 8 carbon atoms as R^1C, R^2C, R^3C, and R^4Cinclude methyl group, ethyl group, propyl group, isopropyl group, butyl group, i-butyl group, t-butyl group, pentyl group, hexyl group, and the like.

Examples of the alkenyl group having 2 to 8 carbon atoms as R^1C, R^2C, R^3C, and R^4Cinclude allyl group, and the like.

Examples of the alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms as R^1C, R^2C, R^3C, and R^4Cinclude methyl group, ethyl group, propyl group, isopropyl group, butyl group, t-butyl group substituted with 1 to 3 halogen atoms such as fluorine atom, chlorine atom, and bromine atom, and the like, and preferred examples of the same include trifluoromethyl group, chloromethyl group, 2-chloroethyl group, 2-bromoethyl group, 2-fluoroethyl group, and the like.

Examples of the aralkyl group (the aryl moiety thereof has 6 to 10 carbon atoms, and the alkylene moiety thereof has 1 to 3 carbon atoms) as R^1C, R^2C, R^3C, and R^4Cinclude benzyl group, and the like.

Examples of the alkoxy group having 1 to 8 carbon atoms as R^1C, R^2C, and R^4Cinclude methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, i-butoxy group, t-butoxy group, pentyloxy group, hexyloxy group, and the like.

Examples of the alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms as R^1C, R^2C, and R^4Cinclude methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, t-butoxy group substituted with 1 to 3 halogen atoms such as fluorine atom, chlorine atom, and bromine atom, and the like, and preferred examples of the same include trifluoromethoxy group, chloromethoxy group, 2-chloroethoxy group, 2-bromoethoxy group, 2-fluoroethoxy group, and the like.

Examples of the halogen atom as R^1C, R^2C, and R^4Cinclude fluorine atom, chlorine atom, bromine atom, and the like.

Examples of the alkylamino group having 1 to 8 carbon atoms as R^1C, R^2C, and R^4Cinclude methylamino group, ethylamino group, and the like.

Examples of the alkylamino group having 1 to 5 carbon atoms and substituted with 1 to 5 halogen atoms as R^4Cinclude 2,2,2-trifluoroethylamino group, and the like.

Examples of the dialkylamino group having 2 to 8 carbon atoms as R^1C, R^2C, and R^4Cinclude dimethylamino group, diethylamino group, and the like.

Examples of the acylamino group having 2 to 8 carbon atoms as R^1C, R^2C, and R^4Cinclude acetylamino group. Examples further include a benzoylamino group which may have a substituent (an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, halogen, and the like).

Examples of the acylamino group having 2 to 8 carbon atoms and substituted with 1 to 3 halogen atoms as R^1C, R^2C, and R^4Cinclude trifluoromethylcarbonylamino group.

Examples of the alkylsulfonylamino group having 1 to 8 carbon atoms as R^1C, R^2C, and R^4Cinclude methylsulfonylamino group.

Examples of the acyl group having 2 to 8 carbon atoms as R^1C, R^2C, and R^4Cinclude acetyl group.

Examples of the alkoxycarbonyl group (the alkoxy moiety thereof has 1 to 8 carbon atoms) as R^1C, R^2C, and R^4Cinclude methoxycarbonyl group, ethoxycarbonyl group, and the like.

Examples of the alkylthio group having 1 to 8 carbon atoms as R^1C, R^2C, and R^4Cinclude methylthio group.

Examples of the alkylsulfinyl group having 1 to 8 carbon atoms as R^1C, R^2C, and R^4Cinclude methylsulfinyl group.

Examples of the alkylsulfonyl group having 1 to 8 carbon atoms as R^1C, R^2C, and R^4Cinclude methylsulfonyl group.

Examples of the alkyl group having 1 to 8 carbon atoms and substituted with hydroxyl group as R^4Cinclude hydroxymethyl group, and the like.

Examples of the benzenesulfonylamino group which may have a substituent as R^4Cinclude a benzenesulfonylamino group which may have a substituent selected from an alkyl group having 1 to 8 carbon atoms (for example, methyl group, ethyl group, and the like), an alkoxy group having 1 to 8 carbon atoms (for example, methoxy group, ethoxy group, and the like), a halogen atom (for example, fluorine atom, chlorine atom, and the like), nitro group, and the like, and preferred examples of the same include o-nitrobenzenesulfonylamino group, and the like.

Preferred examples of the substituent of the phenyl group which may have a substituent as R^4Cinclude an alkyl group having 1 to 8 carbon atoms such as methyl group and ethyl group, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms such as trifluoromethyl group, a halogen atom such as fluorine atom, cyano group, and the like.

Preferred examples of the heterocyclic group of the heterocyclic group which may have a substituent as R^4Cinclude tetrazolyl group, triazolyl group, pyridyl group, imidazolyl group, oxazolyl group, thiazolyl group, and the like. Examples further include oxadiazole group.

Preferred examples of the substituent of the heterocyclic ring which may have a substituent as R^4Cinclude an alkyl group having 1 to 8 carbon atoms such as methyl group and ethyl group, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms such as trifluoromethyl group, a halogen atom such as fluorine atom, cyano group, oxo, and the like.

In the aforementioned general formula (IC), a plurality of the same or different R^1C, R^2C, and R^4Cmay exist on the rings on which R^1C, R^2C, and R^4Csubstitute.

Examples of the alkyl group having 1 to 8 carbon atoms, alkenyl group having 2 to 8 carbon atoms, alkoxy group having 1 to 8 carbon atoms, alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, aralkyl group (the aryl moiety thereof has 6 to 10 carbon atoms, and the alkylene moiety thereof has 1 to 3 carbon atoms), alkyl group having 1 to 8 carbon atoms and substituted with hydroxyl group, halogen atom, alkylamino group having 1 to 8 carbon atoms, alkylamino group having 1 to 5 carbon atoms and substituted with 1 to 5 halogen atoms, dialkylamino group having 2 to 8 carbon atoms, acylamino group having 2 to 8 carbon atoms, acylamino group having 2 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, alkylsulfonylamino group having 1 to 8 carbon atoms, benzenesulfonylamino group which may have a substituent, acyl group having 2 to 8 carbon atoms, alkoxycarbonyl group (the alkoxy moiety thereof has 1 to 8 carbon atoms), alkylthio group having 1 to 8 carbon atoms, alkylsulfinyl group having 1 to 8 carbon atoms, alkylsulfonyl group having 1 to 8 carbon atoms, phenyl group which may have a substituent, heterocyclic group which may have a substituent, and the like as R^11C, R^12C, R^13C, and R^14Cin the aforementioned general formula (IIC) include those similar to those mentioned above for R^1C, R^2C, R^3C, and R^4Cin the general formula C).

Examples of the alkyl group having 1 to 8 carbon atoms, alkoxy group having 1 to 8 carbon atoms, alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, halogen atom, alkylamino group having 1 to 8 carbon atoms, and dialkylamino group having 2 to 8 carbon atoms as the substituent of the heterocyclic group which may have a substituent as R^14Cin the general formula (IIC) include those exemplified for R^1Cto R^4Cin the general formula (IC) mentioned above.

In the aforementioned general formula (IIC), a plurality of the same or different R^11C, R^12C, and R^14Cmay exist on the rings on which R^11C, R^12C, and R^14Csubstitute.

As compounds falling within the scope of the general formula (IC), the following compounds are preferred.

(C-1-1) The compound according to (C-1), wherein R^1Cand R^2Cmay be the same or different, and are hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, or amino group.

(C-1-2) The compound according to (C-1) or (C-1-1), wherein R^3Cis hydrogen atom, or an alkyl group having 1 to 8 carbon atoms.

(C-1-3) The compound according to (C-1), (C-1-1), or (C-1-2), wherein R^4Cis hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkyl group having 1 to 8 carbon atoms and substituted with hydroxyl group, a halogen atom, hydroxyl group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, an alkylsulfonylamino group having 1 to 8 carbon atoms, a benzenesulfonylamino group which may have a substituent, a phenyl group which may have a substituent, or a heterocyclic group which may have a substituent.

(C-1-4) The compound according to (C-1), or any one of (C-1-1) to (C-1-3), wherein R^4Cis a tetrazolyl group, triazolyl group, pyridyl group, imidazolyl group, oxazolyl group, or thiazolyl group which may have a substituent selected from an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, and a dialkylamino group having 2 to 8 carbon atoms.

(C-1-5) The compound according to (C-1), or any one of (C-1-1) to (C-1-4), wherein R^4Cis hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, or a benzenesulfonylamino group which may have a substituent selected from an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a halogen atom, and nitro group.

(C-1-6) The compound according to (C-1), or any one of (C-1-1) to (C-1-5), wherein

embedded image

is a naphthalene ring, tetrahydronaphthalene ring, or indane ring.

(C-1-7) The compound according to (C-1), or any one of (C-1-1) to (C-1-6), wherein

embedded image

is a benzene ring, or indole ring.

(C-2-1) The compound according to (C-2), wherein R^11Cand R^12Cmay be the same or different, and are hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, or amino group.

(C-2-2) The compound according to (C-2) or (C-2-1), wherein R^13Cis hydrogen atom, or an alkyl group having 1 to 8 carbon atoms.

(C-2-3) The compound according to (C-2), (C-2-1), or (C-2-2), wherein R^14Cis hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkyl group having 1 to 8 carbon atoms and substituted with hydroxyl group, a halogen atom, hydroxyl group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, an alkylsulfonylamino group having 1 to 8 carbon atoms, a benzenesulfonylamino group which may have a substituent, a phenyl group which may have a substituent, or a heterocyclic group which may have a substituent.

(C-2-4) The compound according to (C-2), or any one of (C-2-1) to (C-2-3), wherein R^14Cis a tetrazolyl group, triazolyl group, pyridyl group, imidazolyl group, oxazolyl group, or thiazolyl group which may have a substituent selected from an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, and a dialkylamino group having 2 to 8 carbon atoms.

(C-2-5) The compound according to (C-2), or any one of (C-2-1) to (C-2-4), wherein R^14Cis hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, or a benzenesulfonylamino group which may have a substituent selected from an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a halogen atom, and nitro group.

(C-2-6) The compound according to (C-2), or anyone of (C-2-1) to (C-2-5), wherein

embedded image

is a naphthalene ring.

Examples further include the following compounds.

(C-2-7) The compound according to (C-2), wherein R^11C, R^12C, R^13C, and

embedded image

are the same as those of the general formula (IIC), and R^14Cis NHSO₂R^C(R^Crepresents an aryl group which may have a substituent, or a heterocyclic group).

(C-2-8) The compound according to (C-2-7), wherein R^Cis phenyl, naphthyl, quinolyl, pyridyl, or thienyl which may have a substituent selected from an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, hydroxyl group, amino group, nitro, and halogen.

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(In the formula, R^1C, R^3C, and R^4Care as shown in Tables 25 to 27.)

TABLE 25

R^1C
R^3C
R^4C

H
H
3-OH

H
H
3-Ome

H
H
4-OH

H
H
4-Ome

H
H
2-OH

H
H
2-Ome

H
H
2,3-OH

H
H
3-OH, 4-F

H
H
3,4-OH

H
H
3,4-OMe

H
H
3,4,5-OMe

H
H
3-CN

TABLE 26

R^1C
R^3C
R^4C

H
H
4-CN

H
H
3-CO₂H

H
H
3-CO₂Me

H
H
3-Br

H
H
3-F

H
H
4-Me

H
H
3-NH₂

H
H
3-NHSO₂Ph

H
H
3-NHSO₂(2-NO₂)Ph

H
H
4-NHSO₂Ph

H
Me
4-NHSO₂(2-NO₂)Ph

H
Et
3-NHEt

H
H
3-CH₂OH

H
H
4-CH₂OH

TABLE 27

R^1C
R^3C
R^4C

H
H
3-CF₃

H
H
3-Ph

H
H
3-N(Me)₂

H
H
3,5-OH

H
H
4-OAc

H
H
2-Me

9-Me
H
3-NH₂

9-Cl
H
3-NH₂

8-Me
H
3-NH₂

8-Cl
H
3-NH₂

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(In the formula, R^1C, R^3C, R^4C, and R^5Care as shown in Tables 28 to 30.)

TABLE 28

Position

R^1C
R^3C
of R^4C
R^4C
R^5C

H
H
3
1H-Tetrazol-5-yl
H

H
H
4
1H-Tetrazol-5-yl
H

8-Me
H
3
1H-Tetrazol-5-yl
H

8-Cl
H
3
1H-Tetrazol-5-yl
H

H
H
3
1H-Tetrazol-5-yl
4-F

H
H
3
1H-Tetrazol-5-yl
4-Me

H
H
3
1H-Tetrazol-5-yl
5-Br

H
H
3
1H-Tetrazol-5-yl
6-Me

H
H
3
1H-Tetrazol-5-yl
6-Cl

H
H
3
(5-Thioxo-1,2,4-oxadiazol)-3-yl
H

H
H
3
(5-Oxo-1,2,4-oxadiazol)-3-yl
H

H
H
3
(5-Cyano-1H-1,2,3-triazol)-4-yl
H

TABLE 29

Position

R^1C
R^3C
of R^4C
R^4C
R^5C

H
H
3
1H-Tetrazol-5-yl
6-OH

H
H
3
(2-Methyl-2H-tetrazol)-5-yl
H

H
Me
3
(2-Methyl-2H-tetrazol)-5-yl
H

H
Et
3
(2-Ethyl-2H-tetrazol)-5-yl
H

H
H
3
(1-Methyl-1H-tetrazol)-5-yl
H

H
H
3
4-Methyl-(5-thioxo-1,2,4-oxadiazol)-3-yl
H

H
H
3
1-Methyl-1H-imidazol-2-yl
H

H
H
3
1-Methyl-1H-imidazol-4-yl
H

H
H
3
1,3-Oxazol-2-yl
H

H
H
3
1,3-Thiazol-2-yl
H

H
H
3
Pyrrol-2-yl
H

H
H
3
Thiophen-2-yl
H

H
H
3
1-H-Imidazol-2-yl
H

H
H
3
1-H-Imidazol-4-yl
H

TABLE 30

Position

R^1C
R^3C
of R^4C
R^4C
R^5C

H
H
3
Pyrazol-4-yl
H

H
H
3
5-(Chloro)-1H-imidazol-2-yl
H

H
H
3
5-(Trifluoromethyl)-1H-imidazol-2-yl
H

H
H
3
(1,2,3-Triazol)-4-yl
H

H
H
3
(1,2,4-Triazol)-3-yl
H

H
H
3
3-Methyl-(1,2,4-oxadiazol)-5-yl
H

H
H
3
3,5-Dimethylisoxazol-4-yl
H

H
H
3
1-Tetrazol-1-yl
H

H
H
3
Phenyl
H

H
H
3
Pyridin-3-yl
H

H
H
3
Pyrimidin-5-yl
H

H
H
3
2-Aminopyridin-5-yl
H

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(In the formula, R^1C, R^3C, and T^Care as shown in Tables 31 and 32.)

TABLE 31

R^1C
R^3C
T^C

H
H
1H-Indol-6-yl

H
H
1H-Indolin-6-yl

H
H
1H-Indol-4-yl

H
H
1H-Indazol-6-yl

H
Me
1H-Indazol-6-yl

H
Et
1H-Indazol-6-yl

8-Me
H
1H-Indazol-6-yl

8-Cl
H
1H-Indazol-6-yl

H
H
1H-Indazol-4-yl

H
H
1H-Benzimidazol-6-yl

H
H
2-(Trifluoromethyl)-1H-benzimidazol-6-yl

H
H
1H-Benzotriazol-6-yl

TABLE 32

R^1C
R^3C
T^C

H
H
3-Methylbenzoisoxazol-6-yl

H
H
Pyridin-4-yl

H
H
3-Methoxypyridin-5-yl

H
H
3-Hydroxypyridin-5-yl

H
H
Pyridin-3-yl

H
H
7-Hydroxyquinolin-3-yl

H
H
Pyrimidin-2-yl

H
H
Thiophen-2-yl

H
H
Pyridin-2-yl

H
H
4-Methylpyridin-2-yl

H
H
2-Bromopyridin-5-yl

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(In the formula, A^C-B^C-D^C-E^C, R^3C, and R^4Care as shown in Tables 33 to 35.)

TABLE 33

A^C-B^C-D^C-E^C
R^3C
R^4C

CH₂CH₂CH₂CH₂
H
3-OH

CH₂CH₂CH₂CH₂
H
3-OMe

CH₂CH₂CH₂CH₂
H
4-OH

CH₂CH₂CH₂CH₂
H
4-OMe

CH₂CH₂CH₂CH₂
H
2-OH

CH₂CH₂CH₂CH₂
H
2-OMe

CH₂CH₂CH₂CH₂
H
2,3-OH

CH₂CH₂CH₂CH₂
H
3-OH, 4-F

CH₂CH₂CH₂CH₂
H
3,4-OH

CH₂CH₂CH₂CH₂
H
3,4-OMe

CH₂CH₂CH₂CH₂
H
3,4,5-OMe

CH₂CH₂CH₂CH₂
H
3-CN

TABLE 34

A^C-B^C-D^C-E^C
R^3C
R^4C

CH₂NHCH₂CH₂
H
4-CN

CH₂CH₂CH₂CH₂
H
3-CO₂H

CH₂NHCH₂CH₂
H
3-CO₂Me

CH₂CH₂CH₂CH₂
H
3-Br

CH₂CH₂NHCH₂
H
3-F

CH₂CH₂OCH₂
H
4-Me

CH₂CH₂CH₂CH₂
H
3-NH₂

CH₂CH₂CH₂CH₂
H
3-NHSO₂Ph

CH₂CH₂CH₂CH₂
H
3-NHSO₂(2-NO₂)Ph

CH₂CH₂CH₂CH₂
H
4-NHSO₂Ph

CH₂CH₂CH₂CH₂
Me
4-NHSO₂(2-NO₂)Ph

CH₂CH₂CH₂CH₂
Et
3-NHEt

TABLE 35

A^C-B^C-D^C-E^C
R^3C
R^4C

CH₂CH₂CH₂CH₂
H
3-CH₂OH

CH₂CH₂CH₂CH₂
H
3-NHSO₂CH₃

CH₂CH₂CH₂CH₂
H
3-CF3

CH₂CH₂CH₂CH₂
H
3-Ph

CH₂CH₂CH₂CH₂
H
3-N(Me)₂

CH₂CH₂CH₂CH₂
H
3,5-OH

CH₂CH₂CH₂CH₂
H
4-OAc

CH₂CH₂CH₂CH₂
H
2-Me

CH₂CH(Me)CH₂CH₂
H
3-NH₂

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(In the formula, A^C-B^C-D^C-E^C, R^3C, R^4C, and R^5Care as shown in Tables 36 to 38.)

TABLE 36

Position

A^C-B^C-D^C-E^C
R^3C
of R^4C
R^4C
R^5C

CH₂CH₂CH₂CH₂
H
3
1H-Tetrazol-5-yl
H

CH₂CH₂CH₂CH₂
H
4
1H-Tetrazol-5-yl
H

CH₂NHCH₂CH₂
H
3
1H-Tetrazol-5-yl
H

CH₂CH₂OCH₂
H
3
1H-Tetrazol-5-yl
4-F

CH₂CH₂CH₂CH₂
H
3
1H-Tetrazol-5-yl
4-Me

CH₂CH₂CH₂CH₂
H
3
1H-Tetrazol-5-yl
5-Br

CH₂CH₂CH₂CH₂
H
3
1H-Tetrazol-5-yl
6-Me

CH₂CH₂CH₂CH₂
H
3
1H-Tetrazol-5-yl
6-Cl

CH₂CH₂CH₂CH₂
H
3
(5-Thioxo-1,2,4-oxadiazol)-
H

3-yl

CH₂CH₂CH₂CH₂
H
4
(5-Oxo-1,2,4-oxadiazol)-3-yl
H

TABLE 37

Position

A^C-B^C-D^C-E^C
R^3C
of R^4C
R^4C
R^5C

CH₂CH₂CH₂CH₂
H
3
(5-Cyano-1H-1,2,3-triazol)-
H

4-yl

CH₂CH₂CH₂CH₂
H
3
1-H-Tetrazol-5-yl
6-OH

CH₂CH₂CH₂CH₂
H
3
(2-Methyl-2H-tetrazol)-5-yl
H

CH₂CH₂CH₂CH₂
Me
3
(2-Methyl-2H-tetrazol)-5-yl
H

CH₂CH₂CH₂CH₂
Et
3
(2-Ethyl-2H-tetrazol)-5-yl
H

CH₂NHCH₂CH₂
H
3
(1-Methyl-1H-tetrazol)-5-yl
H

CH₂CH₂CH₂CH₂
H
3
4-Methyl-(5-thioxo-1,2,4-
H

oxadiazol)-3-yl

CH₂CH₂CH₂CH₂
H
3
1-Methyl-1H-imidazol-2-yl
H

CH₂CH₂CH₂CH₂
H
3
1-Methyl-1H-imidazol-4-yl
H

CH₂CH₂CH₂CH₂
H
3
1,3-Oxazol-2-yl
H

CH₂CH₂CH₂CH₂
H
3
1,3-Thiazol-2-yl
H

CH₂CH₂CH₂CH₂
H
3
Pyrrol-2-yl
H

CH₂CH₂CH₂CH₂
H
3
Thiophen-2-yl
H

TABLE 38

Position

A^C-B^C-D^C-E^C
R^3C
of R^4C
R^4C
R^5C

CH₂CH₂CH₂CH₂
H
3
1-H-Imidazol-2-yl
H

CH₂CH₂CH₂CH₂
H
3
1-H-Imidazol-4-yl
H

CH₂CH₂CH₂CH₂
H
4
Pyrazol-4-yl
H

CH₂CH₂CH₂CH₂
H
3
5-(Chloro)-1H-imidazol-
H

2-yl

CH₂CH₂CH₂CH₂
H
3
5-(Trifluoromethyl)-1H-
H

imidazol-2-yl

CH₂CH₂CH₂CH₂
H
3
(1,2,3-Triazol)-4-yl
H

CH₂CH₂CH₂CH₂
H
3
(1,2,4-Triazol)-3-yl
H

CH₂CH₂CH₂CH₂
H
3
3-Methyl-(1,2,4-
H

oxadiazol)-5-yl

CH₂CH₂CH₂CH₂
H
4
3,5-Dimethylisoxazol-
H

4-yl

CH₂CH₂CH₂CH₂
H
3
1-Tetrazol-1-yl
H

CH₂CH(Me)CH₂CH₂
H
3
Phenyl
H

CH₂CH₂CH(Me)CH₂
H
3
Pyrimidin-5-yl
H

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(In the formula. A^C-B^C-D^C-E^C, R^3C, and T^Care as shown in Tables 39 and 40.)

TABLE 39

A^C-B^C-D^C-E^C
R^3C
T^C

CH₂CH₂CH₂CH₂
H
1H-Indol-6-yl

CH₂CH₂CH₂CH₂
H
1H-Iindolin-6-yl

CH₂CH₂CH₂CH₂
H
1H-Indol-4-yl

CH₂CH₂CH₂CH₂
H
1H-Indazol-6-yl

CH₂CH₂CH₂CH₂
Me
1H-Indazol-6-yl

CH₂CH₂CH₂CH₂
Et
1H-Indazol-6-yl

CH₂CH₂CH₂CH₂
H
1H-Indazol-4-yl

CH₂CH₂CH₂CH₂
H
1H-Benzimidazol-6-yl

CH₂CH₂CH₂CH₂
H
2-(Trifluoromethyl)-1H-benzimidazol-6-yl

CH₂CH₂CH₂CH₂
H
1H-Benzotriazol-6-yl

CH₂CH₂CH₂CH₂
H
3-Methylbenzoisoxazol-6-yl

TABLE 40

A^C-B^C-D^C-E^C
R^3C
T^C

CH₂CH₂CH₂CH₂
H
Pyridin-4-yl

CH₂CH₂CH₂CH₂
H
3-Methoxypyridin-5-yl

CH₂CH₂CH₂CH₂
H
3-Hydroxypyridin-5-yl

CH₂CH₂CH₂CH₂
H
Pyridin-3-yl

CH₂CH₂CH₂CH₂
H
7-hydroxyquinolin-3-yl

CH₂CH₂CH₂CH₂
H
Pyrimidin-2-yl

CH₂CH₂CH₂CH₂
H
Thiophen-2-yl

CH₂CH₂CH₂CH₂
H
Pyridin-2-yl

CH₂CH₂CH₂CH₂
H
4-Methylpyridin-2-yl

CH₂CH₂CH₂CH₂
H
2-Bromopyridin-5-yl

CH₂CH(Me)CH₂CH₂
H
1H-Indol-6-yl

CH₂CH(Me)CH₂CH₂
H
1H-Indol-5-yl

CH₂CH(Me)CH₂CH₂
H
1H-Indol-4-yl

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(In the formula. A^C-B^C-D^C, R^3C, and R^4Care as shown in Tables 41 to 43.)

TABLE 41

A^C-B^C-D^C
R^3C
R^4C

CH₂CH₂CH₂
H
3-OH

CH₂CH₂CH₂
H
3-OMe

CH₂CH₂CH₂
H
4-OH

CH₂CH₂CH₂
H
4-OMe

OCH₂O
H
2,3-OH

CH₂CH₂CH₂
H
3,4-OH

NHCH₂CH₂
H
3,4,5-OMe

CH₂CH₂CH₂
H
3-CN

TABLE 42

A^C-B^C-D^C
R^3C
R^4C

CH₂CH₂CH₂
H
3-CO₂H

OCH₂O
H
3-Br

CH₂CH₂CH₂
H
4-Me

CH₂NHCH₂
H
3-NHSO₂Ph

CH₂CH₂CH₂
H
3-NHSO₂(2-NO₂)Ph

CH₂CH₂CH₂
H
4-NHSO₂Ph

CH₂CH₂CH₂
Me
4-NHSO₂(2-NO₂)Ph

CH₂CH₂CH₂
Et
3-NHEt

TABLE 43

A^C-B^C-D^C
R^3C
R^4C

CH₂CH₂CH₂
H
3-NHSO₂CH₃

CH₂CH₂CH₂
H
3-Ph

CH₂CH₂CH₂
H
3-N(Me)₂

CH₂CH₂NH
H
2-Me

CH₂CH(Me)CH₂
H
3-NH₂

CH₂CH(Me)CH₂
H
4-NH₂

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(In the formula. A^C-B^C-D^C, R^3C, R^4C, and R^5Care as shown in Tables 44 to 46.)

TABLE 44

Position

A^C-B^C-D^C
R^3C
of R^4C
R^4C
R^5C

CH₂CH₂CH₂
H
3
1H-Tetrazol-5-yl
H

OCH₂O
H
4
1H-Tetrazol-5-yl
H

CH₂CH(Me)CH₂
H
3
1H-Tetrazol-5-yl
H

CH₂CH(Me)CH₂
H
4
1H-Tetrazol-5-yl
H

CH₂CH₂CH₂
H
3
1H-Tetrazol-5-yl
4-F

CH₂CH₂CH₂
H
3
1H-Tetrazol-5-yl
4-Me

CH₂CH₂CH₂
H
3
1H-Tetrazol-5-yl
5-Br

CH₂NHCH₂
H
3
1H-Tetrazol-5-yl
6-Me

CH₂CH₂CH₂
H
3
(5-Thioxo-1,2,4-oxadiazol)-
H

3-yl

TABLE 45

Position

A^C-B^C-D^C
R^3C
of R^4C
R^4C
R^5C

CH₂CH₂CH₂
H
3
1H-Tetrazol-5-yl
6-OH

CH₂CH₂CH₂
H
3
(2-Methyl-2H-tetrazol)-5-yl
H

CH₂CH₂CH₂
Me
3
(2-Methyl-2H-tetrazol)-5-yl
H

CH₂CH₂CH₂
Et
3
(2-Ethyl-2H-tetrazol)-5-yl
H

CH₂CH₂CH₂
H
3
4-Methyl-(5-thioxo-1,2,4-
H

oxadiazol)-3-yl

CH₂CH₂CH₂
H
3
1-Methyl-1H-imidazol-2-yl
H

CH₂CH₂CH₂
H
3
1,3-Oxazol-2-yl
H

CH₂CH₂CH₂
H
3
1,3-Thiazol-2-yl
H

CH₂CH₂CH₂
H
3
Thiophen-2-yl
H

TABLE 46

Position

A^C-B^C-D^C
R^3C
of R^4C
R^4C
R^5C

CH₂CH₂CH₂
H
3
1H-Imidazol-4-yl
H

CH₂CH₂CH₂
H
3
Pyrazol-4-yl
H

CH₂CH₂CH₂
H
3
5-(Chloro)-1H-imidazol-2-yl
H

CH₂CH₂CH₂
H
3
(1,2,4-Triazol)-3-yl
H

CH₂CH₂CH₂
H
3
1-Tetrazol-1-yl
H

OCH₂O
H
3
Phenyl
H

CH₂CH₂CH₂
H
3
Pyridin-3-yl
H

NHCH₂CH₂
H
3
Pyrimidin-5-yl
H

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(In the formula, A^C-B^C-D^C, R^3C, and T^Care as shown in Tables 47 and 48.)

TABLE 47

A^C-B^C-D^C
R^3C
T^C

CH₂CH₂CH₂
H
1H-Indol-6-yl

OCH₂O
H
1H-Indolin-6-yl

CH₂CH₂CH₂
Me
1H-Indazol-6-yl

CH₂CH₂CH₂
Et
1H-Indazol-6-yl

CH₂CH₂CH₂
H
1H-Indazol-4-yl

CH₂NHCH₂
H
1H-Benzotriazol-6-yl

CH₂CH₂CH₂
H
3-Methylbenzisoxazol-6-yl

TABLE 48

A^C-B^C-D^C
R^3C
T^C

CH₂CH₂CH₂
H
Pyridin-4-yl

CH₂CH₂CH₂
H
Thiophen-2-yl

CH₂NHCH₂
H
4-Methylpyridin-2-yl

CH₂CH(Me)CH₂
H
1H-Indol-6-yl

(D-1) A compound represented by the following general formula (ID):

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wherein, in the formula, R^1Dand R^2Dmay be the same or different, and represent hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an aralkyl group (the aryl moiety thereof has 6 to 10 carbon atoms, and the alkylene moiety thereof has 1 to 3 carbon atoms), a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, an acylamino group having 2 to 8 carbon atoms, an acylamino group having 2 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkylsulfonylamino group having 1 to 8 carbon atoms, carboxyl group, an acyl group having 2 to 8 carbon atoms, an alkoxycarbonyl group (the alkoxy moiety thereof has 1 to 8 carbon atoms), carbamoyl group, an alkylthio group having 1 to 8 carbon atoms, an alkylsulfinyl group having 1 to 8 carbon atoms, an alkylsulfonyl group having 1 to 8 carbon atoms, or sulfamoyl group,

R^3Drepresents hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, or an aralkyl group (the aryl moiety thereof has 6 to 10 carbon atoms, and the alkylene moiety thereof has 1 to 3 carbon atoms),

R^4Drepresents hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an aralkyl group (the aryl moiety thereof has 6 to 10 carbon atoms, and the alkylene moiety thereof has 1 to 3 carbon atoms), an alkyl group having 1 to 8 carbon atoms and substituted with hydroxyl group, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, an alkylamino group having 1 to 5 carbon atoms and substituted with 1 to 5 halogen atoms, a dialkylamino group having 2 to 8 carbon atoms, an acylamino group having 2 to 8 carbon atoms, an acylamino group having 2 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkylsulfonylamino group having 1 to 8 carbon atoms, a benzenesulfonylamino group which may have a substituent, carboxyl group, an acyl group having 2 to 8 carbon atoms, an alkoxycarbonyl group (the alkoxy moiety thereof has 1 to 8 carbon atoms), carbamoyl group, an alkylthio group having 1 to 8 carbon atoms, an alkylsulfinyl group having 1 to 8 carbon atoms, an alkylsulfonyl group having 1 to 8 carbon atoms, sulfamoyl group, a phenyl group which may have a substituent, or a heterocyclic group which may have a substituent,

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represents a 5- to 8-membered ring which condenses at, the 1- and 2-positions of the benzene ring, and may contain 1 or 2 nitrogen atoms as ring-constituting elements, and

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represents an aromatic ring selected from benzene ring, naphthalene ring, pyridine ring, pyrimidine ring, quinoline ring, indole ring, indoline ring, benzimidazole ring, pyrazole ring, indazole ring, benzisoxazole ring, and benzotriazole ring.

(D-2) A compound represented by the following general formula (IID):

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wherein, in the formula, R^11Dand R^12Dmay be the same or different, and represent hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an aralkyl group (the aryl moiety thereof has 6 to 10 carbon atoms, and the alkylene moiety thereof has 1 to 3 carbon atoms), a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, an acylamino group having 2 to 8 carbon atoms, an acylamino group having 2 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkylsulfonylamino group having 1 to 8 carbon atoms, carboxyl group, an acyl group having 2 to 8 carbon atoms, an alkoxycarbonyl group (the alkoxy moiety thereof has 1 to 8 carbon atoms), carbamoyl group, an alkylthio group having 1 to 8 carbon atoms, an alkylsulfinyl group having 1 to 8 carbon atoms, an alkylsulfonyl group having 1 to 8 carbon atoms, or sulfamoyl group.

R^13Drepresents hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, or an aralkyl group (the aryl moiety thereof has 6 to 10 carbon atoms, and the alkylene moiety thereof has 1 to 3 carbon atoms),

R^14Drepresents an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an aralkyl group (the aryl moiety thereof has 6 to 10 carbon atoms, and the alkylene moiety thereof has 1 to 3 carbon atoms), an alkyl group having 1 to 8 carbon atoms and substituted with hydroxyl group, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, an alkylamino group having 1 to 5 carbon atoms and substituted with 1 to 5 halogen atoms, a dialkylamino group having 2 to 8 carbon atoms, an acylamino group having 2 to 8 carbon atoms, an acylamino group having 2 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkylsulfonylamino group having 1 to 8 carbon atoms, a benzenesulfonylamino group which may have a substituent, carboxyl group, an acyl group having 2 to 8 carbon atoms, an alkoxycarbonyl group (the alkoxy moiety thereof has 1 to 8 carbon atoms), carbamoyl group, an alkylthio group having 1 to 8 carbon atoms, an alkylsulfinyl group having 1 to 8 carbon atoms, an alkylsulfonyl group having 1 to 8 carbon atoms, sulfamoyl group, a phenyl group which may have a substituent, or a heterocyclic group which may have a substituent, and,

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represents naphthalene ring, tetrahydronaphthalene ring, or indane ring.

As for the general formula (II), examples of the alkyl group having 1 to 8 carbon atoms as R^1D, R^2D, R^3D, and R^4Dinclude methyl group, ethyl group, propyl group, isopropyl group, butyl group, i-butyl group, t-butyl group, pentyl group, hexyl group, and the like.

Examples of the alkenyl group having 2 to 8 carbon atoms as R^1D, R^2D, R^3D, and R^4Dinclude allyl group, and the like.

Examples of the alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms as R^1D, R^2D, R^3D, and R^4Dinclude methyl group, ethyl group, propyl group, isopropyl group, butyl group, t-butyl group substituted with 1 to 3 halogen atoms such as fluorine atom, chlorine atom, and bromine atom, and the like, and preferred examples of the same include trifluoromethyl group, chloromethyl group, 2-chloroethyl group, 2-bromoethyl group, 2-fluoroethyl group, and the like.

Examples of the aralkyl group (the aryl moiety thereof has 6 to 10 carbon atoms, and the alkylene moiety thereof has 1 to 3 carbon atoms) as R^1D, R^2D, R^3D, and R^4Dinclude benzyl group, and the like.

Examples of the alkoxy group having 1 to 8 carbon atoms as R^1D, R^2D, and R^4Dinclude methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, i-butoxy group, t-butoxy group, pentyloxy group, hexyloxy group, and the like.

Examples of the alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms as R^1D, R^2D, and R^4Dinclude methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, t-butoxy group substituted with 1 to 3 halogen atoms such as fluorine atom, chlorine atom, and bromine atom, and the like, and preferred examples of the same include trifluoromethoxy group, chloromethoxy group, 2-chloroethoxy group, 2-bromoethoxy group, 2-fluoroethoxy group, and the like.

Examples of the halogen atom as R^1D, R^2D, and R^4Dinclude fluorine atom, chlorine atom, bromine atom, and the like.

Examples of the alkylamino group having 1 to 8 carbon atoms as R^1D, R^2D, and R^4Dinclude methylamino group, ethylamino group, and the like.

Examples of the alkylamino group having 1 to 5 carbon atoms and substituted with 1 to 5 halogen atoms as R⁴include 2,2,2-trifluoroethylamino group, and the like.

Examples of the dialkylamino group having 2 to 8 carbon atoms as R^1D, R^2D, and R^4Dinclude dimethylamino group, diethylamino group, and the like.

Examples of the acylamino group having 2 to 8 carbon atoms as R^1D, R^2D, and R^4Dinclude acetylamino group.

Examples of the acylamino group having 2 to 8 carbon atoms and substituted with 1 to 3 halogen atoms as R^1D, R^2D, and R^4Dinclude trifluoromethylcarbonylamino group.

Examples of the alkylsulfonylamino group having 1 to 8 carbon atoms as R^1D, R^2D, and R^4Dinclude methylsulfonylamino group.

Examples of the acyl group having 2 to 8 carbon atoms as R^1D, R^2D, and R^4Dinclude acetyl group.

Examples of the alkoxycarbonyl group (the alkoxy moiety thereof has 1 to 8 carbon atoms) as R^1D, R^2D, and R^4Dinclude methoxycarbonyl group, ethoxycarbonyl group, and the like.

Examples of the alkylthio group having 1 to 8 carbon atoms as R^1D, R^2D, and R^4Dinclude methylthio group.

Examples of the alkylsulfinyl group having 1 to 8 carbon atoms as R^1D, R^2D, and R^4Dinclude methylsulfinyl group.

Examples of the alkylsulfonyl group having 1 to 8 carbon atoms as R^1D, R^2D, and R^4Dinclude methylsulfonyl group.

Examples of the alkyl group having 1 to 8 carbon atoms and substituted with hydroxyl group as R^4Dinclude hydroxymethyl group, and the like.

Examples of the benzenesulfonylamino group which may have a substituent as R^4Dinclude a benzenesulfonylamino group which may have a substituent selected from an alkyl group having 1 to 8 carbon atoms (for example, methyl group, ethyl group, and the like), an alkoxy group having 1 to 8 carbon atoms (for example, methoxy group, ethoxy group, and the like), a halogen atom (for example, fluorine atom, chlorine atom, and the like), nitro group, and the like, and preferred examples of the same include o-nitrobenzenesulfonylamino group, and the like.

Preferred examples of the substituent of the phenyl group which may have a substituent as R^4Dinclude an alkyl group having 1 to 8 carbon atoms such as methyl group and ethyl group, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms such as trifluoromethyl group, a halogen atom such as fluorine atom, cyano group, and the like.

Preferred examples of the heterocyclic group of the heterocyclic group which may have a substituent as R^4Dinclude a tetrazolyl group, triazolyl group, pyridyl group, imidazolyl group, oxazolyl group, thiazolyl group, and the like.

Preferred examples of the substituent of the heterocyclic ring which may have a substituent as R^4Dinclude an alkyl group having 1 to 8 carbon atoms such as methyl group and ethyl group, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms such as trifluoromethyl group, a halogen atom such as fluorine atom, cyano group, oxo, and the like.

In the general formula (ID), a plurality of the same or different R^1D, R^2D, and R^4Dmay exist on the rings on which R^1D, R^2D, and R^4Dsubstitute.

Examples of the alkyl group having 1 to 8 carbon atoms, alkenyl group having 2 to 8 carbon atoms, alkoxy group having 1 to 8 carbon atoms, alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, aralkyl group (the aryl moiety thereof has 6 to 10 carbon atoms, and the alkylene moiety thereof has 1 to 3 carbon atoms), alkyl group having 1 to 8 carbon atoms and substituted with hydroxyl group, halogen atom, alkylamino group having 1 to 8 carbon atoms, alkylamino group having 1 to 5 carbon atoms and substituted with 1 to 5 halogen atoms, dialkylamino group having 2 to 8 carbon atoms, acylamino group having 2 to 8 carbon atoms, acylamino group having 2 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, alkylsulfonylamino group having 1 to 8 carbon atoms, benzenesulfonylamino group which may have a substituent, acyl group having 2 to 8 carbon atoms, alkoxycarbonyl group (the alkoxy moiety thereof has 1 to 8 carbon atoms), alkylthio group having 1 to 8 carbon atoms, alkylsulfinyl group having 1 to 8 carbon atoms, alkylsulfonyl group having 1 to 8 carbon atoms, phenyl group which may have a substituent, heterocyclic group which may have a substituent, and the like as R^11D, R^12D, R^13D, and R^14Din the aforementioned general formula (ID) include those similar to the examples of the same as R^1D, R^2D, R^3D, and R^4Din the general formula (ID) mentioned above.

Examples of the alkyl group having 1 to 8 carbon atoms, alkoxy group having 1 to 8 carbon atoms, alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, halogen atom, alkylamino group having 1 to 8 carbon atoms, and dialkylamino group having 2 to 8 carbon atoms as the substituent of the heterocyclic group which may have a substituent as R^14Din the general formula (ID) include the examples of the same mentioned for R^1Dto R^4Dof the general formula (ID) mentioned above.

In the aforementioned general formula (IID), a plurality of the same or different R^11D, R^12D, and R^14Dmay exist on the rings on which R^11D, R^12D, and R^14Dsubstitute.

As the compounds of the general formula (ID), the following compounds are preferred.

(D-1-1) The compound according to (D-1), wherein R^1Dand R^2Dmay be the same or different, and are hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, or amino group.

(D-1-2) The compound according to (D-1) or (D-1-1), wherein R^3Dis hydrogen atom, or an alkyl group having 1 to 8 carbon atoms.

(D-1-3) The compound according to any one of (D-1), (D-1-1), and (D-1-2), wherein R^4Dis hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkyl group having 1 to 8 carbon atoms and substituted with hydroxyl group, a halogen atom, hydroxyl group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, an alkylsulfonylamino group having 1 to 8 carbon atoms, a benzenesulfonylamino group which may have a substituent, a phenyl group which may have a substituent, or a heterocyclic group which may have a substituent.

(D-1-4) The compound according to (D-1), or any one of (D-1-1) to (D-1-3), wherein R^4Dis a tetrazolyl group, triazolyl group, pyridyl group, imidazolyl group, oxazolyl group, or thiazolyl group which may have a substituent selected from an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, and a dialkylamino group having 2 to 8 carbon atoms.

(D-1-5) The compound according to (D-1), or any one of (D-1-1) to (D-1-4), wherein R^4Dis an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, hydroxyl group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, or a benzenesulfonylamino group which may have a substituent selected from an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a halogen atom, and nitro group.

(D-1-6) The compound according to (D-1), or any one of (D-1-1) to (D-1-5), wherein

embedded image

is a naphthalene ring, tetrahydronaphthalene ring, or indane ring.

(D-1-7) The compound according to (D-1), or any one of (D-1-1) to (D-1-6), wherein

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is a benzene ring, or indole ring.

As the compounds represented by the general formula (IID), the following compounds are preferred.

(D-2-1) The compound according to (D-2), wherein R^11Dand R^12Dmay be the same or different, and are hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, or amino group.

(D-2-2) The compound according to (D-2) or (D-2-1), wherein R^13Dis hydrogen atom.

(D-2-3) The compound according to any one of (D-2), (D-2-1), and (D-2-2), wherein R^14Dis an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkyl group having 1 to 8 carbon atoms and substituted with hydroxyl group, hydroxyl group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, an alkylsulfonylamino group having 1 to 8 carbon atoms, a benzenesulfonylamino group which may have a substituent, a phenyl group which may have a substituent, or a heterocyclic group which may have a substituent.

(D-2-4) The compound according to (D-2), or any one of (D-2-1) to (D-2-3), wherein R^14Dis a tetrazolyl group, triazolyl group, pyridyl group, imidazolyl group, oxazolyl group, or thiazolyl group which may have a substituent selected from an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, and a dialkylamino group having 2 to 8 carbon atoms.

(D-2-5) The compound according to (D-2), or any one of (D-2-1) to (D-2-4), wherein R^14Dis an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, hydroxyl group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, or a benzenesulfonylamino group which may have a substituent selected from an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a halogen atom, and nitro group.

(D-2-6) The compound according to (D-2), or any one of (D-2-1) to (D-2-5), wherein

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is a naphthalene ring.

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(In the formula, R^1D, R^3D, and R^4Dare as shown in Table 49.)

TABLE 49

R^1D
R^3D
R^4D

H
H
3-OH

8-Me
H
3-OMe

8-Cl
H
4-OH

9-Me
H
3,4-OH

9-Cl
H
3-CN

H
H
4-CN

H
H
3-CO₂H

H
H
3-NH₂

H
H
3-NHMe

H
Me
3-NHMe

H
Et
3-NHEt

H
H
3-NHCH₂CF₃

H
H
3-NHSO₂Ph

H
H
3-NHSO₂(2-NO₂)Ph

H
H
1H-Tetrazol-5-yl

H
H
1H-Tetrazol-1-yl

H
H
(2-Methyl-2H-tetrazol)-5-yl

H
H
1,3-Oxazol-2-yl

H
H
1-H-Imidazol-2-yl

H
H
(1,2,4-Triazol)-3-yl

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(In the formula, R^1D, R^3D, and T^Dare as shown in Table 50.)

TABLE 50

R^1D
R^3D
T^D

H
H
1H-Indol-6-yl

8-Me
H
1H-Indol-4-yl

8-Cl
H
1H-Indazol-6-yl

9-Me
H
1H-Indazol-4-yl

9-Cl
H
1H-Indolin-6-yl

H
Me
1H-Benzimidazol-6-yl

H
Et
1H-Benzotriazol-6-yl

H
H
3-Methylbenzisoxazol-6-yl

H
H
Pyridin-3-yl

H
H
1H-Pyrazol-4-yl

H
H
Pyridin-2-yl

H
H
4-Methylpyridin-2-yl

H
H
2-Bromopyridin-5-yl

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(In the formula. A^D-B^D-D^D-E^D, R^3D, and R^4Dare as shown in Table 51.)

TABLE 51

A^D-B^D-D^D-E^D
R^3D
R^4D

CH₂CH₂CH₂CH₂
H
3-OH

CH₂CH₂CH₂
H
3-OMe

CH₂CH₂(CH₂)₂CH₂
H
4-OH

CH₂CH₂(CH₂)₃CH₂
H
3,4-OH

CH₂CH₂CH₂CH₂
H
3-CN

CH₂CH₂NHCH₂
H
4-CN

CH₂CH₂CH₂CH₂
H
3-CO₂H

CH₂CH₂NHCH₂
H
3-NH₂

CH₂CH₂CH₂CH₂
H
3-NHMe

CH₂CH₂CH₂CH₂
Me
3-NHMe

CH₂CH₂CH₂CH₂
Et
3-NHEt

CH₂CH₂CH₂CH₂
H
3-NHCH₂CF₃

CH₂CH₂CH₂CH₂
H
3-NHSO₂Ph

CH₂CH₂CH₂CH₂
H
3-NHSO₂(2-NO₂)Ph

CH₂CH₂CH₂CH₂
H
1H-Tetrazol-5-yl

CH₂NHCH₂CH₂
H
1H-Tetrazol-1-yl

CH₂CH(Me)CH₂CH₂
H
(2-Methyl-2H-tetrazol)-5-yl

CH₂CH(Me)CH₂CH₂
H
1,3-Oxazol-2-yl

CH₂CH₂CH(Me)CH₂
H
1H-Imidazol-2-yl

CH₂CH₂CH(Me)CH₂
H
(1,2,4-Triazol)-3-yl

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(In the formula, A^D-B^D-D^D-E^D, R^3D, and T^Dare as shown in Table 52.)

TABLE 52

A^D-B^D-D^D-E^D
R^3D
T^D

CH₂CH₂CH₂CH₂
H
1H-Indol-6-yl

CH₂CH₂CH₂
H
1H-Indol-4-yl

CH₂CH₂(CH₂)₂CH₂
H
1H-Indazol-6-yl

CH₂CH₂(CH₂)₃CH₂
H
1H-Indazol-4-yl

CH₂CH₂CH₂CH₂
Me
1H-Indolin-6-yl

CH₂NHCH₂CH₂
Et
1H-Benzimidazol-6-yl

CH₂CH₂CH₂CH₂
H
1H-Benzotriazol-6-yl

CH₂CH₂CH₂CH₂
H
3-Methylbenzisoxazol-6-yl

CH₂CH₂CH₂CH₂
H
Pyridin-3-yl

CH₂N(Me)CH₂CH₂
H
1H-Pyrazol-4-yl

CH₂CH(Me)CH₂CH₂
H
Pyridin-2-yl

CH₂CH₂CH(Me)CH₂
H
4-Methylpyridin-2-yl

CH₂CH₂CH(Me)CH₂
H
2-Bromopyridin-5-yl

(E-1) A compound represented by the following general formula (IE):

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wherein, in the formula, R^1Eand R^2Emay be the same or different, and represent hydrogen atom, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, an acylamino group having 2 to 8 carbon atoms, carboxyl group, an acyl group having 2 to 8 carbon atoms, an alkoxycarbonyl group (the alkoxy moiety thereof has 1 to 8 carbon atoms), a phenyl group which may have a substituent, a pyridyl group which may have a substituent, or an aralkyl group (the aryl moiety thereof has 6 to 10 carbon atoms, and the alkylene moiety thereof has 1 to 8 carbon atoms), or

R^1Eand R^2Emay bind together to form a condensed ring selected from naphthalene ring, quinoline ring, isoquinoline ring, tetrahydronaphthalene ring, indane ring, tetrahydroquinoline ring, and tetrahydroisoquinoline ring together with the benzene ring to which they bind, and the ring formed by R^1E, R^2Ebinding together, and the carbon atoms to which R^1Eand R^2Ebind may be substituted with 1 to 4 of the same or different substituents selected from an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, an acylamino group having 2 to 8 carbon atoms, carboxyl group, an acyl group having 2 to 8 carbon atoms, an alkoxycarbonyl group (the alkoxy moiety thereof has 1 to 8 carbon atoms), and an aralkyl group (the aryl moiety thereof has 6 to 10 carbon atoms, and the alkylene moiety thereof has 1 to 8 carbon atoms).

R^3Eand R^4Emay be the same or different, and represent hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, an acylamino group having 2 to 8 carbon atoms, carboxyl group, an acyl group having 2 to 8 carbon atoms, an alkoxycarbonyl group (the alkoxy moiety thereof has 1 to 8 carbon atoms), or an aralkyl group (the aryl moiety thereof has 6 to 10 carbon atoms, and the alkylene moiety thereof has 1 to 8 carbon atoms),

R^5Erepresents hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkyl group having 1 to 8 carbon atoms and substituted with hydroxyl group, or an aralkyl group (the aryl moiety thereof has 6 to 10 carbon atoms, and the alkylene moiety thereof has 1 to 8 carbon atoms).

R^6Eand R^7Emay be the same or different, and represent hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, or amino group.

X^Erepresents C, CH, or N,

Y^Erepresents N. NH, or C(═O),

provided that when X^Eis N, Y^Eis not N or NH, and

when X^Eis C or CH. Y^Eis not C(═O),

the double line consisting of the solid line and the broken line represents a single bond or a double bond.

Z^Erepresents oxygen atom or sulfur atom,

A^Erepresents benzene ring, pyridine ring, thiophene ring, pyrimidine ring, naphthalene ring, quinoline ring, or indole ring which may have 1 to 4 of the same or different substituents selected from an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, an aralkyl group (the aryl moiety thereof has 6 to 10 carbon atoms, and the alkylene moiety thereof has 1 to 8 carbon atoms), phenyl group, and pyridyl group, or an atomic bond.

B^Erepresents N(R^8E)C(═O). NHCONH, CON(R^9E), NHC(═S)NH, N(R^10E)SO₂, SO₂N(R^11E), or OSO₂, wherein

R^8E, R^9E, R^10E, and R^11Erepresent hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkyl group having 1 to 8 carbon atoms and substituted with hydroxyl group, or an aralkyl group (the aryl moiety thereof has 6 to 10 carbon atoms, and the alkylene moiety thereof has 1 to 8 carbon atoms).

D^Erepresents an alkylene chain having 1 to 6 carbon atoms which may have 1 to 4 of the same or different substituents selected from an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkyl group having 1 to 8 carbon atoms and substituted with hydroxyl group, or an aralkyl group (the aryl moiety thereof has 6 to 10 carbon atoms, and the alkylene moiety thereof has 1 to 8 carbon atoms), and may further contain a double bond, or an atomic bond,

E^Erepresents, S, NR^12E, or an atomic bond, wherein

R^12Erepresents hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkyl group having 1 to 8 carbon atoms and substituted with hydroxyl group, or an aralkyl group (the aryl moiety thereof has 6 to 10 carbon atoms, and the alkylene moiety thereof has 1 to 8 carbon atoms),

G^Erepresents piperazine, piperidine, morpholine, cyclohexane, benzene, naphthalene, quinoline, quinoxaline, benzimidazole, thiophene, imidazole, thiazole, oxazole, indole, benzofuran, pyrrole, pyridine, or pyrimidine which may have 1 to 4 of the same or different substituents selected from an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, an acyl group having 2 to 8 carbon atoms, methylenedioxy group, carboxyl group, an alkylsulfinyl group having 1 to 6 carbon atoms, an alkylthio group having 1 to 6 carbon atoms, an alkylsulfonyl group having 1 to 6 carbon atoms, an aralkyl group (the aryl moiety thereof has 6 to 10 carbon atoms, and the alkylene moiety thereof has 1 to 8 carbon atoms), a phenyl group which may have a substituent, a pyridyl group which may have a substituent, an imidazolyl group which may have a substituent, an oxazolyl group may have a substituent, and a thiazolyl group which may have a substituent, and

m^Erepresents an integer of 0 to 5,

provided that compounds where R^1Eand R^2Edo not bind together to form a ring, X^Eis C. Y^Eis N, the double line consisting of the solid line and the broken line is a double bond, Z^Eis oxygen atom. A^Eis a benzene ring, m^Eis 0. B^Eis C(═O)NH, E^Eis an atomic bond, and G^Eis phenyl group are excluded.

(E-2) A compound represented by the following general formula (IIE):

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wherein in the formula

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represents naphthalene ring, quinoline ring, isoquinoline ring, tetrahydronaphthalene ring, indane ring, tetrahydroquinoline ring, or tetrahydroisoquinoline ring, and

these rings may be substituted with 1 to 4 of the same or different substituents selected from an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, an acylamino group having 2 to 8 carbon atoms, carboxyl group, an acyl group having 2 to 8 carbon atoms, an alkoxycarbonyl group (the alkoxy moiety thereof has 1 to 8 carbon atoms), and an aralkyl group (the aryl moiety thereof has 6 to 10 carbon atoms, and the alkylene moiety thereof has 1 to 8 carbon atoms).

R^3aEand R^4aEmay be the same or different, and represent hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, an acylamino group having 2 to 8 carbon atoms, carboxyl group, an acyl group having 2 to 8 carbon atoms, an alkoxycarbonyl group (the alkoxy moiety thereof has 1 to 8 carbon atoms), or an aralkyl group (the aryl moiety thereof has 6 to 10 carbon atoms, and the alkylene moiety thereof has 1 to 8 carbon atoms),

R^5aErepresents hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkyl group having 1 to 8 carbon atoms and substituted with hydroxyl group, or an aralkyl group (the aryl moiety thereof has 6 to 10 carbon atoms, and the alkylene moiety thereof has 1 to 8 carbon atoms).

R^6aEand R^7aEmay be the same or different, and represent hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, or amino group.

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represents benzene ring, pyridine ring, thiophene ring, pyrimidine ring, naphthalene ring, quinoline ring, or indole ring which may have 1 to 4 of the same or different substituents selected from an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, an aralkyl group (the aryl moiety thereof has 6 to 10 carbon atoms, and the alkylene moiety thereof has 1 to 8 carbon atoms), phenyl group, and pyridyl group,

B^aErepresents N(R^8aE)C(═O), NHCONH, CON(R^9aE), NHC(═S)NH, N(R^10aE)SO₂. SO₂N(R^11aE), or OSO₂, wherein

R^8aE, R^9aE, R^10aE, and R^11aErepresent hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkyl group having 1 to 8 carbon atoms and substituted with hydroxyl group, or an aralkyl group (the aryl moiety thereof has 6 to 10 carbon atoms, and the alkylene moiety thereof has 1 to 8 carbon atoms).

E^aErepresents O. S. NR^12aE, or an atomic bond, wherein

R^12aErepresents hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkyl group having 1 to 8 carbon atoms and substituted with hydroxyl group, or an aralkyl group (the aryl moiety thereof has 6 to 10 carbon atoms, and the alkylene moiety thereof has 1 to 8 carbon atoms).

G^aErepresents piperazine, piperidine, morpholine, cyclohexane, benzene, naphthalene, quinoline, quinoxaline, benzimidazole, thiophene, imidazole, thiazole, oxazole, indole, benzofuran, pyrrole, pyridine, or pyrimidine which may have 1 to 4 of the same or different substituents selected from an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, an acyl group having 2 to 8 carbon atoms, methylenedioxy group, carboxyl group, an alkylsulfinyl group having 1 to 6 carbon atoms, an alkylthio group having 1 to 6 carbon atoms, an alkylsulfonyl group having 1 to 6 carbon atoms, an aralkyl group (the aryl moiety thereof has 6 to 10 carbon atoms, and the alkylene moiety thereof has 1 to 8 carbon atoms), a phenyl group which may have a substituent, a pyridyl group which may have a substituent, an imidazolyl group which may have a substituent, an oxazolyl group which may have a substituent, and a thiazolyl group which may have a substituent, and

n^Erepresents an integer of 0 to 5.

As for the general formulas (IE) and (IIE), examples of the alkyl group having 1 to 8 carbon atoms include methyl group, ethyl group, propyl group, isopropyl group, butyl group, i-butyl group, t-butyl group, pentyl group, hexyl group, and the like.

Examples of the cycloalkyl group having 3 to 8 carbon atoms include cyclopropyl group, cyclohexyl group, and the like.

Examples of the alkenyl group having 2 to 8 carbon atoms include allyl group, and the like.

Examples of the alkoxy group having 1 to 8 carbon atoms include methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, i-butoxy group, t-butoxy group, pentyloxy group, hexyloxy group, and the like.

Examples of the alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms include methyl group, ethyl group, propyl group, isopropyl group, butyl group, t-butyl group substituted with 1 to 3 halogen atoms such as fluorine atom, chlorine atom, and bromine atom, and the like, and preferred examples of the same include trifluoromethyl group, chloromethyl group, 2-chloroethyl group, 2-bromoethyl group, 2-fluoroethyl group, and the like.

Examples of the alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms include methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, t-butoxy group substituted with 1 to 3 halogen atoms such as fluorine atom, chlorine atom, and bromine atom, and the like, and preferred examples of the same include trifluoromethoxy group, chloromethoxy group, 2-chloroethoxy group, 2-bromoethoxy group, 2-fluoroethoxy group, and the like.

Examples of the halogen atom include fluorine atom, chlorine atom, bromine atom, and the like.

Examples of the alkylamino group having 1 to 8 carbon atoms include methylamino group, ethylamino group, and the like.

Examples of the dialkylamino group having 2 to 8 carbon atoms include dimethylamino group, diethylamino group, and the like.

Examples of the acylamino group having 2 to 8 carbon atoms include acetylamino group.

Examples of the acyl group having 2 to 8 carbon atoms include acetyl group, and the like.

Examples of the alkoxycarbonyl group (the alkoxy moiety thereof has 1 to 8 carbon atoms) include methoxycarbonyl group, and the like.

Examples of the aralkyl group (the aryl moiety thereof has 6 to 10 carbon atoms, and the alkylene moiety thereof has 1 to 8 carbon atoms) include benzyl group, and the like.

Examples of the alkyl group having 1 to 8 carbon atoms and substituted with hydroxyl group include 2-hydroxyethyl group, and the like.

Examples of the alkylsulfinyl group having 1 to 6 carbon atoms include methanesulfinyl group, and the like.

Examples of the alkylthio group having 1 to 6 carbon atoms include methylthio group, and the like.

Examples of the alkylsulfonyl group having 1 to 6 carbon atoms include methanesulfonyl group, and the like.

Examples of the substituent of the phenyl group which may have a substituent, pyridyl group which may have a substituent, imidazolyl group which may have a substituent, oxazolyl group which may have a substituent, and thiazolyl group which may have a substituent, include a halogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, and the like.

As the compounds of the general formula (IE) of the present invention, the following compounds are preferred.

(E-1-1) The compound according to (E-1), wherein R^1E, and R^2Emay be the same or different, and are hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, a phenyl group which may have a substituent, a pyridyl group which may have a substituent, or an aralkyl group (the aryl moiety thereof has 6 to 10 carbon atoms, and the alkylene moiety thereof has 1 to 8 carbon atoms).

(E-1-2) The compound according to (E-1), wherein R^1Eand R^2Ebind together to form naphthalene ring, or tetrahydronaphthalene ring together with the benzene ring to which they bind, and the benzene ring, or cyclohexene ring formed by R^1E, R^2Ebinding together, and the carbon atoms to which R^1Eand R^2Ebind may be substituted with 1 to 4 of the same or different substituents selected from an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, an acylamino group having 2 to 8 carbon atoms, carboxyl group, an acyl group having 2 to 8 carbon atoms, an alkoxycarbonyl group (the alkoxy moiety thereof has 1 to 8 carbon atoms), and an aralkyl group (the aryl moiety thereof has 6 to 10 carbon atoms, and the alkylene moiety thereof has 1 to 8 carbon atoms).

(E-1-3) The compound according to (E-1), wherein R^1Eand R^2Ebind together to form naphthalene ring together with the benzene ring to which they bind, and the benzene ring formed by R^1E, R^2Ebinding together, and the carbon atoms to which R^1Eand R^2Ebind may be substituted with 1 to 4 of the same or different substituents selected from an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, and amino group.

(E-1-4) The compound according to (E-1), or any one of (E-1-1) to (E-1-3), wherein R^3Eand R^4Emay be the same or different, and are hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, or an aralkyl group (the aryl moiety thereof has 6 to 10 carbon atoms, and the alkylene moiety thereof has 1 to 8 carbon atoms).

(E-1-5) The compound according to (E-1), or any one of (E-1-1) to (E-1-4), wherein R^5Eis hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or an aralkyl group (the aryl moiety thereof has 6 to 10 carbon atoms, and the alkylene moiety thereof has 1 to 8 carbon atoms).

(E-1-6) The compound according to (E-1), or any one of (E-1-1) to (E-1-5), wherein R^5Eis hydrogen atom.

(E-1-7) The compound according to (E-1), or any one of (E-1-1) to (E-1-6), wherein R^6Eand R^7Emay be the same or different, and are hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, or an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms.

(E-1-8) The compound according to (E-1), or any one of (E-1-1) to (E-1-7), wherein both R^6Eand R^7Eare hydrogen atoms.

(E-1-9) The compound according to (E-1), or any one of (E-1-1) to (E-1-8), wherein X^Eis N, Y^Eis C(═O), and the double line consisting of the solid line and the broken line is a single bond.

(E-1-10) The compound according to (E-1), or any one of (E-1-1) to (E-1-9), wherein X^Eis C. Y^Eis N, and the double line consisting of the solid line and the broken line is a double bond.

(E-1-11) The compound according to (E-1), or any one of (E-1-1) to (E-1-10), wherein Z^Eis oxygen atom.

(E-1-12) The compound according to (E-1), or any one of (E-1-1) to (E-1-11), wherein A^Eis a phenyl group or pyridyl group which may have 1 to 4 of the same or different substituents selected from an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, an aralkyl group (the aryl moiety thereof has 6 to 10 carbon atoms, and the alkylene moiety thereof has 1 to 8 carbon atoms), phenyl group, and pyridyl group.

(E-1-13) The compound according to (E-1), or any one of (E-1-1) to (E-1-12), wherein A^Eis a phenyl group which may have 1 to 4 of the same or different substituents selected from an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, and amino group.

(E-1-14) The compound according to (E-1), or any one of (E-1-1) to (E-1-13), wherein A^Eis an atomic bond.

(E-1-15) The compound according to (E-1), or any one of (E-1-1) to (E-1-14), wherein B^Eis NHC(═O). NHCONH, CONH, NHC(═S)NH. NHSO₂, SO₂NH, or OSO₂.

(E-1-16) The compound according to (E-1), or any one of (E-1-1) to (E-1-15), wherein B^Eis NHC(═O), NHCONH, or NHSO₂.

(E-1-17) The compound according to (E-1), or any one of (E-1-1) to (E-1-16), wherein D^Eis an alkylene chain having 1 to 6 carbon atoms which may have 1 to 4 of the same or different substituents selected from an alkyl group having 1 to 8 carbon atoms, and an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, and may further contain a double bond.

(E-1-18) The compound according to (E-1), or any one of (E-1-1) to (E-1-16), wherein D^Eis an atomic bond.

(E-1-19) The compound according to (E-1), or any one of (E-1-1) to (E-1-18), wherein E^Eis an atomic bond.

(E-1-20) The compound according to (E-1), or any one of (E-1-1) to (E-1-19), wherein G^Eis piperazine, piperidine, morpholine, cyclohexane, benzene, naphthalene, quinoline, quinoxaline, benzimidazole, thiophene, imidazole, thiazole, oxazole, indole, benzofuran, pyrrole, pyridine, or pyrimidine which may have 1 to 4 of the same or different substituents selected from an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, an acyl group having 2 to 8 carbon atoms, methylenedioxy group, carboxyl group, an alkylsulfinyl group having 1 to 6 carbon atoms, an alkylthio group having 1 to 6 carbon atoms, and an alkylsulfonyl group having 1 to 6 carbon atoms.

(E-1-21) The compound according to (E-1), or any one of (E-1-1) to (E-1-20), wherein G^Eis benzene which may have 1 to 4 of the same or different substituents selected from an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, an acyl group having 2 to 8 carbon atoms, methylenedioxy group, carboxyl group, an alkylsulfinyl group having 1 to 6 carbon atoms, an alkylthio group having 1 to 6 carbon atoms, and an alkylsulfonyl group having 1 to 6 carbon atoms.

(E-1-22) The compound according to (E-1), or any one of (E-1-1) to (E-1-21), wherein mF is 0.

As the compounds represented by the general formula (IIE), the following compounds are preferred.

(E-2-1) The compound according to (E-2), wherein

embedded image

is a naphthalene ring or tetrahydronaphthalene ring which may be substituted with 1 to 4 of the same or different substituents selected from an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, an acylamino group having 2 to 8 carbon atoms, carboxyl group, an acyl group having 2 to 8 carbon atoms, an alkoxycarbonyl group (the alkoxy moiety thereof has 1 to 8 carbon atoms), and an aralkyl group (the aryl moiety thereof has 6 to 10 carbon atoms, and the alkylene moiety thereof has 1 to 8 carbon atoms).

(E-2-2) The compound according to (E-2), wherein

embedded image

is a naphthalene ring which may be substituted with 1 to 4 of the same or different substituents selected from an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, and amino group.

(E-2-3) The compound according to (E-2), (E-2-1), or (E-2-2), wherein R^3aEand R^4aEmay be the same or different, and are hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, or an aralkyl group (the aryl moiety thereof has 6 to 10 carbon atoms, and the alkylene moiety thereof has 1 to 8 carbon atoms).

(E-2-4) The compound according to (E-2), or any one of (E-2-1) to (E-2-3), wherein R^5aEis hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or an aralkyl group (the aryl moiety thereof has 6 to 10 carbon atoms, and the alkylene moiety has 1 to 8 carbon atoms).

(E-2-5) The compound according to (E-2), or any one of (E-2-1) to (E-2-4), wherein R^5aEis hydrogen atom.

(E-2-6) The compound according to (E-2), or any one of (E-2-1) to (E-2-5), wherein R^6aEand R^7aEmay be the same or different, and are hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, or an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms.

(E-2-7) The compound according to (E-2), or any one of (E-2-1) to (E-2-6), wherein both R^6aEand R^7aEare hydrogen atoms.

(E-2-8) The compound according to (E-2), or any one of (E-2-1) to (E-2-7), wherein

embedded image

is a phenyl group or pyridyl group which may have 1 to 4 of the same or different substituents selected from an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, an aralkyl group (the aryl moiety thereof has 6 to 10 carbon atoms, and the alkylene moiety thereof has 1 to 8 carbon atoms), phenyl group, and pyridyl group.

(E-2-9) The compound according to (E-2), or anyone of (E-2-1) to (E-2-8), wherein

embedded image

is a phenyl group which may have 1 to 4 of the same or different substituents selected from an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, and amino group.

(E-2-10) The compound according to (E-2), or any one of (E-2-1) to (E-2-7), wherein

embedded image

is an atomic bond

(E-2-11) The compound according to (E-2), or any one of (E-2-1) to (E-2-10), wherein B^aEis NHC(═O). NHCONH, CONH, NHC(═S)NH. NHSO₂, SO₂NH, or OSO₂.

(E-2-12) The compound according to (E-2), or any one of (E-2-1) to (E-2-11), wherein B^aEis NHC(═O), NHCONH, or NHSO₂.

(E-2-13) The compound according to (E-2), or any one of (E-2-1) to (E-2-10), wherein E^aEis an atomic bond.

(E-2-14) The compound according to (E-2), or any one of (E-2-1) to (E-2-13), wherein G^aEis piperazine, piperidine, morpholine, cyclohexane, benzene, naphthalene, quinoline, quinoxaline, benzimidazole, thiophene, imidazole, thiazole, oxazole, indole, benzofuran, pyrrole, pyridine, or pyrimidine which may have 1 to 4 of the same or different substituents selected from an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, an acyl group having 2 to 8 carbon atoms, methylenedioxy group, carboxyl group, an alkylsulfinyl group having 1 to 6 carbon atoms, an alkylthio group having 1 to 6 carbon atoms, and an alkylsulfonyl group having 1 to 6 carbon atoms.

(E-2-15) The compound according to (E-2), or any one of (E-2-1) to (E-2-14), wherein G^aEis benzene which may have 1 to 4 of the same or different substituents selected from an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, an acyl group having 2 to 8 carbon atoms, methylenedioxy group, carboxyl group, an alkylsulfinyl group having 1 to 6 carbon atoms, an alkylthio group having 1 to 6 carbon atoms, and an alkylsulfonyl group having 1 to 6 carbon atoms.

(E-2-16) The compound according to (E-2), or any one of (E-2-1) to (E-2-15), wherein n^Eis 0.

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(In the formula, B^aE(substitution position), n^E, E^aE, and G^Eare as shown in Tables 53 to 61.)

TABLE 53

B^aE(substitution

position)
n^E
E^aE
G^aE

NHCO(4)
0
Atomic bond
Phenyl

NHCO(4)
0
Atomic bond
(2-CF₃)Phenyl

NHCO(4)
0
Atomic bond
(3-Br)Phenyl

NHCO(4)
0
Atomic bond
(4-CF₃)Phenyl

NHCO(4)
0
Atomic bond
(2-Me)Phenyl

NHCO(4)
0
Atomic bond
(2,6-Me)Phenyl

NHCO(4)
0
Atomic bond
(2,6-Cl)Phenyl

NHCO(4)
0
Atomic bond
(3-Cl)Phenyl

NHCO(4)
1
Atomic bond
Phenyl

NHC(═S)NH(4)
0
Atomic bond
Phenyl

NHCO(4)
0
Atomic bond
(2,3-OMe)Phenyl

NHCO(4)
0
Atomic bond
(2-OMe)Phenyl

NHCO(4)
1
Atomic bond
(2-Cl)Phenyl

NHCO(4)
0
Atomic bond
(2,3-Me)Phenyl

NHCO(4)
0
Atomic bond
(2,5-Me)Phenyl

NHCO(4)
0
Atomic bond
(2-Cl, 5-Br)Phenyl

TABLE 54

B^aE(substitution

position)
n^E
E^aE
G^aE

NHCO(4)
0
Atomic bond
(2,4-Cl)Phenyl

NHCO(4)
0
Atomic bond
(2-OH)Phenyl

NHCO(4)
0
Atomic bond
(2,3-OH)Phenyl

NHC(═O)NH(4)
0
Atomic bond
Phenyl

NHCO(4)
1
Atomic bond
(2,6-Cl)Phenyl

NHCO(4)
1
Atomic bond
(2-OMe)Phenyl

NHCO(4)
1
Atomic bond
(2-OH)Phenyl

NHC(═S)NH(4)
0
Atomic bond
(2-Cl)Phenyl

NHCO(4)
0
Atomic bond
(3-CF₃)Phenyl

NHCO(4)
1
Atomic bond
(2-CF₃)Phenyl

NHC(═O)NH(4)
0
Atomic bond
(2-Cl)Phenyl

NHCO(4)
0
Atomic bond
(2-Cl, 3-OMe)Phenyl

NHCO(4)
2
Atomic bond
Phenyl

NHCO(4)
0
Atomic bond
3-Indolyl

NHCO(4)
0
Atomic bond
(2-Cl, 3-OH)Phenyl

NHCO(4)
1
O
Phenyl

TABLE 55

B^aE(substitution

position)
n^E
E^aE
G^aE

NHCO(4)
1
Atomic bond
(2-Cl, 4-OMe)Phenyl

NHCO(4)
0
Atomic bond
(1-Me)Imidazol-2-yl

NHCO(4)
1
Atomic bond
(2,4-Cl)Phenyl

NHCO(4)
1
Atomic bond
(2-Cl, 4-OH)Phenyl

NHCO(4)
1
Atomic bond
Pyridin-3-yl

NHCO(4)
0
Atomic bond
Benzimidazol-2-yl

NHCO(4)
0
Atomic bond
(2-Cl)Phenyl

NHCO(4)
0
Atomic bond
(2-Br)Phenyl

NHCO(4)
0
Atomic bond
(2-I)Phenyl

NHCO(4)
1
Atomic bond
(2-Me)Phenyl

NHCO(4)
0
Atomic bond
Quinoxalin-2-yl

NHCO(4)
0
Atomic bond
(5-Me)Thiophen-2-yl

NHCO(3)
1
Atomic bond
(2-Cl)Phenyl

NHCO(4)
0
Atomic bond
(2,4,6-Me)Phenyl

NHCO(4)
0
Atomic bond
(2-Et)Phenyl

NHC(═S)NH(4)
0
Atomic bond
(2-Me)Phenyl

TABLE 56

B^aE(substitution

position)
n^E
E^aE
G^aE

NHCO(4)
0
Atomic bond
(4-NMe₂)Phenyl

NHCO(4)
1
O
(2,4-Cl)Phenyl

NHCO(4)
1
O
(2-Me)Phenyl

NHCO(4)
0
Atomic bond
(2-Ac)Phenyl

NHCO(4)
0
Atomic bond
(2-tBu)Phenyl

NHCO(3)
0
Atomic bond
(2-I)Phenyl

NHCO(4)
0
Atomic bond
(1-Me)Piperidin-4-yl

NHCO(4)
0
Atomic bond
Benzofuran-2-yl

NHCO(4)
0
Atomic bond
(1-Me)Indol-3-yl

NHCO(4)
0
Atomic bond
(2-Allyl)phenyl

NHCO(4)
0
Atomic bond
(2-nPr)Phenyl

NHCO(4)
0
Atomic bond
(2-iPrO)Phenyl

NHCO(4)
0
Atomic bond
(3-Me)Thiophen-2-yl

NHCO(4)
1
O
(2-Me, 3-Cl)Phenyl

NHCO(4)
0
Atomic bond
(2-CF₃, 4-F)Phenyl

NHCO(4)
0
Atomic bond
(2-OMe, 4-F)Phenyl

TABLE 57

B^aE(substitution

position)
n^E
E^aE
G^aE

NHCO(4)
0
Atomic bond
(2-OH, 4-F)Phenyl

NHCO(3)
1
Atomic bond
(2-I)Phenyl

NHCO(4)
0
Atomic bond
(3-NMe₂)Phenyl

NHCO(4)
0
Atomic bond
(2-OMe, 4-I)Phenyl

NHCO(4)
0
Atomic bond
(2-OMe, 6-F)Phenyl

NHCO(4)
0
Atomic bond
(2-OH, 4-I)Phenyl

NHCO(4)
0
Atomic bond
(2-OH, 6-F)Phenyl

NHCO(4)
0
Atomic bond
(2-F)Phenyl

NHCO(4)
0
Atomic bond
(2-NMe₂)Phenyl

NHCO(4)
0
Atomic bond
(2-OMe, 6-Me)Phenyl

NHCO(4)
0
Atomic bond
(2-OH, 6-Me)Phenyl

NHCO(4)
2
Atomic bond
(2-Me)Phenyl

CONH(4)
0
Atomic bond
Phenyl

CONH(4)
1
Atomic bond
Phenyl

NHCO(4)
2
Atomic bond
(2-Cl)Phenyl

CONH(4)
1
Atomic bond
(2-Cl)Phenyl

TABLE 58

B^aE(substitution

position)
n^E
E^aE
G^aE

CONH(4)
0
Atomic bond
(2-Cl)Phenyl

NHCO(4)
0
Atomic bond
(5-Br, 2,3-Methylenedioxy)phenyl

NHCO(4)
0
Atomic bond
(2-OMe, 6-Br)Phenyl

NHCO(4)
0
Atomic bond
(2-OH, 6-Br)Phenyl

NHCO(4)
0
Atomic bond
(2-OMe, 6-Cl)Phenyl

NHCO(4)
0
Atomic bond
(2-OH, 6-Cl)Phenyl

NHCO(4)
0
Atomic bond
(2-OH, 6-OMe)Phenyl

NHCO(4)
0
Atomic bond
(2-OMe, 6-CF₃)Phenyl

NHCO(4)
0
Atomic bond
(2-OH, 6-CF₃)Phenyl

NHCO(4)
0
Atomic bond
(2-Cl, 5-SMe)Phenyl

NHCO(4)
0
Atomic bond
(2-SMe)Phenyl

NHCO(4)
0
Atomic bond
(3-SMe)Phenyl

NHCO(4)
0
Atomic bond
(2-OMe, 6-Et)Phenyl

NHCO(4)
0
Atomic bond
(3-SO₂Me)Phenyl

NHCO(4)
0
Atomic bond
(2-OH, 6-Et)Phenyl

NHCO(4)
0
Atomic bond
(3-S(═O)Me)Phenyl

TABLE 59

B^aE(substitution

position)
n^E
E^aE
G^aE

NHCO(4)
0
Atomic bond
(2-Cl, 5-S(═O)Me)Phenyl

NHCO(4)
0
Atomic bond
(2-S(═O)Me)Phenyl

NHCO(4)
0
Atomic bond
(3-Cl)Pyridin-2-yl

NHCO(4)
0
Atomic bond
(2-OMe, 3-Cl)Phenyl

NHCO(4)
0
Atomic bond
(3-Me)Pyridin-2-yl

NHCO(4)
0
Atomic bond
(2-OH, 3-Cl)Phenyl

NHCO(4)
0
Atomic bond
(3-OH)Pyridin-2-yl

NHCO(4)
0
Atomic bond
(3-Vinyl)pyridin-2-yl

NHCO(4)
0
Atomic bond
(2-Et)Pyridin-2-yl

NHSO₂(4)
0
Atomic bond
(2-NO₂)Phenyl

NHSO₂(4)
0
Atomic bond
Phenyl

NHSO₂(4)
0
Atomic bond
(3-Br)Phenyl

NHSO₂(4)
0
Atomic bond
(3-OMe)Phenyl

NHSO₂(3)
0
Atomic bond
(2-NO₂)Phenyl

NMeSO₂(3)
0
Atomic bond
(2-NO₂)Phenyl

NHSO₂(3)
0
Atomic bond
Naphthalen-2-yl

TABLE 60

B^aE(substitution

position)
n^E
E^aE
G^aE

NHSO₂(3)
0
Atomic bond
Naphthalen-1-yl

NHSO₂(4)
0
Atomic bond
Cyclohexyl

NHSO₂(4)
0
Atomic bond
Pyridin-3-yl

NHSO₂(4)
0
Atomic bond
(4-iPr)Phenyl

NHSO₂(4)
1
Atomic bond
Phenyl

NHSO₂(4)
0
Atomic bond
Thiophen-2-yl

NHSO₂(4)
0
Atomic bond
Naphthalen-2-yl

NBnSO₂(4)
0
Atomic bond
(2-NO₂)Phenyl

NMeSO₂(4)
0
Atomic bond
(3-Br)Phenyl

NMeSO₂(4)
0
Atomic bond
(2-NO₂)Phenyl

N(CH₂CH₂OH)SO₂(4)
0
Atomic bond
(2-NO₂)Phenyl

NHSO₂(4)
1
Atomic bond
(2-Cl)Phenyl

NHSO₂(4)
1
Atomic bond
(3-Br)Phenyl

NHSO₂(4)
0
Atomic bond
(2-CF₃)Phenyl

NHSO₂(4)
1
Atomic bond
(2-Br)Phenyl

NHSO₂(4)
1
Atomic bond
(2-Me)Phenyl

TABLE 61

B^aE(substitution

position)
n^E
E^aE
G^aE

NHSO₂(4)
1
Atomic bond
(2-NO₂)Phenyl

NHSO₂(4)
2
Atomic bond
Phenyl

NHSO₂(4)
1
Atomic bond
(4-Cl)Phenyl

NMeSO₂(4)
1
Atomic bond
(2-CF₃)Phenyl

NMeSO₂(4)
1
Atomic bond
(2-Et)Phenyl

NMeSO₂(4)
1
Atomic bond
(2,3-Me)Phenyl

NMeSO₂(4)
2
Atomic bond
(2-Cl)Phenyl

NMeSO₂(4)
1
Atomic bond
(2-NO₂)Phenyl

NMeSO₂(4)
1
Atomic bond
(2-NH₂)Phenyl

NMeSO₂(4)
1
Atomic bond
(2-NMe₂)Phenyl

TABLE 62

B^aE(substitution

position)
n^E
E^aE
G^aE

NHCO(4)
0
Atomic bond
Pyridin-4-yl

NHCO(4)
1
O
Pyridin-3-yl

NHCO(4)
0
Atomic bond
Pyridin-3-yl

NHCO(4)
0
Atomic bond
(2-Me)Pyridin-3-yl

NHCO(4)
0
Atomic bond
(2-Cl)Pyridin-3-yl

NHCO(4)
1
O
Pyridin-2-yl

NHCO(4)
0
Atomic bond
(4-CF₃)Pyridin-3-yl

NHCO(4)
0
Atomic bond
(2-iPr)Phenyl

embedded image

(In the formula, B^aE(substitution position), n^E, E^aE, and G^aEare as shown in Tables 63 and 64.)

TABLE 63

B^aE(substitution

position)
n^E
E^aE
G^aE

NHCO(4)
0
Atomic bond
Cyclohexyl

NHCO(4)
0
Atomic bond
(6-Me)Pyridin-2-yl

NHCO(4)
0
Atomic bond
(2-Me)Pyridin-3-yl

NHCO(4)
0
Atomic bond
(2-OMe, 3-Me)Phenyl

NHCO(4)
0
Atomic bond
(2,3-Cl)Phenyl

NHCO(4)
0
Atomic bond
(2-OH, 3-Me)Phenyl

NHCO(4)
0
Atomic bond
(2-I)Phenyl

NHCO(4)
1
Atomic bond
(1-Me)Pyrrol-2-yl

NHCO(4)
1
Atomic bond
(2-tBu)Phenyl

NHCO(4)
0
Atomic bond
(2-Isopropenyl)phenyl

NHCO(4)
0
Atomic bond
(2-iPr)Phenyl

NHCO(4)
1
Atomic bond
Morpholin-2-yl

NHCO(4)
0
Atomic bond
(2-Cl)Pyridin-2-yl

TABLE 64

B^aE(substitution

position)
n^E
E^aE
G^aE

NHSO₂(4)
0
Atomic bond
(2-NO₂)Phenyl

NMeSO₂(4)
0
Atomic bond
(2-NO₂)Phenyl

SO₂NH(4)
0
Atomic bond
Phenyl

OSO₂(4)
0
Atomic bond
(3-Br)Phenyl

NHSO₂(4)
1
Atomic bond
(2-Cl)Phenyl

NHSO₂(4)
0
Atomic bond
(3-Br)Phenyl

NHSO₂(4)
0
Atomic bond
(3-OMe)Phenyl

NHSO₂(4)
1
Atomic bond
(2,3-Cl)Phenyl

NHSO₂(4)
1
Atomic bond
(2,6-Cl)Phenyl

NHSO₂(4)
1
Atomic bond
(2-I)Phenyl

NMeSO₂(4)
1
Atomic bond
(2-Cl)Phenyl

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(In the formula, R^1E. B^aE(substitution position), n^E, E^aE, and G^aEare as shown in Table 65.)

TABLE 65

B^aE

(substitution

R^1E
position)
n^E
E^aE
G^aE

7-OMe
NHCO(4)
0
Atomic bond
(2,3-Me)Phenyl

7-OH
NHCO(4)
0
Atomic bond
(2,3-Me)Phenyl

6-Me
NHCO(4)
0
Atomic bond
(2,3-Me)Phenyl

6,7-Me
NHCO(4)
0
Atomic bond
(2-I)Phenyl

6-Et
NHCO(4)
0
Atomic bond
(2-I)Phenyl

7-Ph
NHCO(4)
0
Atomic bond
(2-Isopropyl)phenyl

7-(Pyridin-3-yl)
NHCO(4)
0
Atomic bond
(2-Isopropyl)phenyl

7-(Pyridin-2-yl)
NHCO(4)
0
Atomic bond
(2-Isopropyl)phenyl

7-Cl
NHSO₂(4)
0
Atomic bond
(2-Isopropyl)phenyl

7-Br
NHSO₂(4)
0
Atomic bond
(2-Isopropyl)phenyl

7-CF₃
NHSO₂(4)
0
Atomic bond
(2-Isopropyl)phenyl

H
NHSO₂(4)
0
Atomic bond
(2-Isopropyl)phenyl

6-Me, 7-Br
NHSO₂(4)
0
Atomic bond
(2-Isopropyl)phenyl

7-OMe
NHSO₂(4)
1
Atomic bond
(2-Cl)Phenyl

7-OH
NHSO₂(4)
1
Atomic bond
(2-Cl)Phenyl

6-Me
NHSO₂(4)
1
Atomic bond
(2-Cl)Phenyl

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(In the formula. B^aE(substitution position), n, E^aE, and G^aEare as shown in Table 66.)

TABLE 66

B^aE(substitution

position)
n^E
E^aE
G^aE

NHCO
0
Atomic bond
(2-Cl, 3-OMe)Phenyl

NHCO
0
Atomic bond
(2-I)Phenyl

NHSO₂
1
Atomic bond
(2-Cl)Phenyl

NHSO₂
1
Atomic bond
(2-Cl)Phenyl

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(In the formula, B^aE(substitution position), n^E, E^aE, and G^Eare as shown in Table 67.)

TABLE 67

B^aE(substitution

position)
n^E
E^aE
G^aE

NHCO(4)
0
Atomic bond
(2-Cl, 3-Ome)Phenyl

NHCO(4)
0
Atomic bond
(2-Cl, 3-OH)Phenyl

NHCO(4)
0
Atomic bond
(2-tBu)Phenyl

NHCO(4)
0
Atomic bond
(2-Cl, 6-Ome)Phenyl

NHCO(4)
0
Atomic bond
(2-Cl, 6-OH)Phenyl

NHSO₂(3)
0
Atomic bond
Phenyl

NHSO₂(4)
1
Atomic bond
(2-Cl)Phenyl

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(In the formula, B^E(substitution position), D^E, E^E, and G^Eare as shown in Table 68.)

TABLE 68

B^E(substitution

position)
D^E
E^E
G^E

NHCO(4)
C(Me)H
Atomic bond
Phenyl

NHCO(4)
C(Me)₂
Atomic bond
Phenyl

NHCO(4)
CH═CH
Atomic bond
Phenyl

NHCO(4)
C(Me)H
O
Phenyl

NHCO(4)
C(Me)₂
O
Phenyl

NHCO(4)
CH═CH
Atomic bond
(2-Me)Phenyl

NHCO(4)
CH═CH
Atomic bond
(2-Cl)Phenyl

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(In the formula, m^E(substitution position), B^E, D^E, E^E, and G^Eare as shown in Table 69.)

TABLE 69

m^E(substitution

position)
B^E
D^E
E^E
G^E

1(4)
NHCO
Atomic bond
Atomic bond
Phenyl

1(4)
NHCO
Atomic bond
Atomic bond
(2-Cl)Phenyl

1(4)
NHSO₂
CH₂
Atomic bond
(2-Cl)Phenyl

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(In the formula, X^aE, Y^aE, B^aE(substitution position), n^E, E^aE, and G^aEare as shown in Table 70.)

TABLE 70

B^aE

(substitution

X^aE
Y^aE
position)
n^E
E^aE
G^aE

CH
C—F
NHCO(4)
0
Atomic bond
(2,3-Me)Phenyl

CH
C—OH
NHCO(4)
0
Atomic bond
(2,3-Me)Phenyl

CH
C—F
NHCO(4)
0
Atomic bond
(2-I)Phenyl

CH
N
NHCO(4)
0
Atomic bond
(2-I)Phenyl

CH
N
NHCO(4)
0
Atomic bond
Phenyl

N
CH
NHCO(4)
0
Atomic bond
(2-I)Phenyl

CH
N
NHCO(4)
0
Atomic bond
(2-Cl)Phenyl

CH
N
NHCO(4)
0
Atomic bond
(2-OH)Phenyl

CH
N
NHC(═O)NH(4)
0
Atomic bond
(2-OH)Phenyl

CH
N
NHCO(4)
0
Atomic bond
(2-OH,

6-Me)Phenyl

CH
N
NHCO(4)
0
Atomic bond
(2-OH,

6-Cl)Phenyl

CH
N
NHCO(3)
0
Atomic bond
(2-OH,

6-Cl)Phenyl

CH
N
NHCO(4)
0
Atomic bond
(2-Cl)Pyridin-

2-yl

CH
N
NHCO(4)
1
Atomic bond
(2-Cl)Pyridin-

2-yl

CH
N
NHCO(4)
0
Atomic bond
(2-Me)Pyridin-

2-yl

CH
C—OMe
NHSO₂(4)
1
Atomic bond
(2-Cl)Phenyl

CH
C—OH
NHSO₂(4)
1
Atomic bond
(2-Cl)Phenyl

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(In the formula. I^E═II^E-III^E═IV^E, B^aE(substitution position). E, E^aE, and G^Eare as shown in Table 71.)

TABLE 71

B^aE

(substitution

I^E═II^E═III^E═IV^E
position)
n^E
E^aE
G^aE

N═CH—CH═CH
NHCO(4)
0
Atomic bond
(2-I)Phenyl

CH═N—CH═CH
NHCO(4)
0
Atomic bond
(2-I)Phenyl

CH═CH—N═CH
NHCO(4)
0
Atomic bond
(2-I)Phenyl

CH═CH—CH═N
NHCO(4)
0
Atomic bond
(2-I)Phenyl

N═CH—CH═CH
NHCO(4)
1
O
Phenyl

N═CH—CH═CH
NHCO(3)
0
Atomic bond
(2-I)Phenyl

N═CH—CH═CH
NHCO(4)
0
Atomic bond
(2-Cl)Phenyl

N═CH—CH═CH
NHCO(4)
0
Atomic bond
(2-OH)Phenyl

N═CH—CH═CH
NHC(═O)NH(4)
0
Atomic bond
(2-OH)Phenyl

N═CH—CH═CH
NHCO(4)
1
O
(2-OH, 6-Me)Phenyl

N═CH—CH═CH
NHCO(4)
0
Atomic bond
(2-OH, 6-Cl)Phenyl

N═CH—CH═CH
NHCO(3)
0
Atomic bond
(2-OH, 6-Cl)Phenyl

N═CH—CH═CH
NHCO(4)
0
Atomic bond
(2-Cl)Pyridin-2-yl

N═CH—CH═CH
NHCO(4)
1
Atomic bond
(2-Cl)Pyridin-2-yl

N═CH—CH═CH
NHCO(4)
0
Atomic bond
(2-Me)Pyridin-2-yl

CH═CH—N═CH
NHCO(4)
0
Atomic bond
(2-Cl)Pyridin-3-yl

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(In the formula. I^E—II^E—III^E—IV^E, B^aE(substitution position), n^E, E^aE, and G^aEare as shown in Table 72.)

TABLE 72

B^aE

(substitution

I^E-II^E-III^E-IV^E
position)
n^E
E^aE
G^aE

NH—CH₂—CH₂—CH₂
NHCO(4)
0
Atomic bond
(2-I)Phenyl

CH₂—NH—CH₂—CH₂
NHCO(4)
0
Atomic bond
(2-I)Phenyl

CH₂—CH₂—NH—CH₂
NHCO(4)
0
Atomic bond
(2-I)Phenyl

CH₂—CH₂—CH₂—NH
NHCO(4)
0
Atomic bond
(2-I)Phenyl

CH₂—CH₂—NH—CH₂
NHCO(4)
1
O
Phenyl

CH₂—CH₂—NH—CH₂
NHCO(3)
0
Atomic bond
(2-I)Phenyl

CH₂—CH₂—NH—CH₂
NHCO(4)
0
Atomic bond
(2-Cl)Phenyl

CH₂—CH₂—NH—CH₂
NHCO(4)
0
Atomic bond
(2-Cl)Pyridin-3-yl

CH₂—CH₂—NH—CH₂
NHCO(4)
0
Atomic bond
(2-OH)Phenyl

CH₂—CH₂—NH—CH₂
NHC(═O)NH(4)
0
Atomic bond
(2-OH)Phenyl

CH₂—CH₂—NH—CH₂
NHCO(4)
1
O
(2-OH, 6-Me)Phenyl

CH₂—CH₂—NH—CH₂
NHCO(4)
0
Atomic bond
(2-OH, 6-Cl)Phenyl

CH₂—CH₂—NH—CH₂
NHCO(3)
0
Atomic bond
(2-OH, 6-Cl)Phenyl

CH₂—CH₂—NH—CH₂
NHCO(4)
0
Atomic bond
(2-Cl)Pyridin-2-yl

CH₂—CH₂—NH—CH₂
NHCO(4)
1
Atomic bond
(2-Cl)Pyridin-2-yl

CH₂—CH₂—NH—CH₂
NHCO(4)
0
Atomic bond
(2-Me)Pyridin-2-yl

CH₂—CH₂—NH—CH₂
NHCO(4)
0
Atomic bond
(2-Cl)Pyridin-3-yl

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(In the formula, R^5aE(substitution position), n^E, E^aE, and G^aEare as shown in Table 73.)

TABLE 73

B^aE

(substitution

R^5aE
position)
n^E
E^aE
G^aE

Bn
NBnSO₂(4)
0
Atomic bond
(2-NO₂)Phenyl

Me
NBnSO₂(4)
0
Atomic bond
(2-NO₂)Phenyl

Et
NBnSO₂(4)
0
Atomic bond
(2-NO₂)Phenyl

(F-1) A compound represented by the following general formula (F):

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wherein, in the formula, R^1Fand R^2Fmay be the same or different, and represent hydrogen atom, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, an acylamino group having 2 to 8 carbon atoms, carboxyl group, an acyl group having 2 to 8 carbon atoms, an alkoxycarbonyl group (the alkoxy moiety thereof has 1 to 8 carbon atoms), a phenyl group which may have a substituent, a pyridyl group which may have a substituent, or an aralkyl group (the aryl moiety thereof has 6 to 10 carbon atoms, and the alkylene moiety thereof has 1 to 8 carbon atoms).

R^1Fand R^2Fmay bind together to form a condensed ring selected from naphthalene ring, quinoline ring, isoquinoline ring, tetrahydronaphthalene ring, indane ring, tetrahydroquinoline ring, and tetrahydroisoquinoline ring together with the benzene ring to which they bind, and the ring consisting of R^1F, R^2Fbinding together, and the carbon atoms to which R^1Fand R^2Fbind may be substituted with 1 to 4 of the same or different substituents selected from an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, an acylamino group having 2 to 8 carbon atoms, carboxyl group, an acyl group having 2 to 8 carbon atoms, an alkoxycarbonyl group (the alkoxy moiety thereof has 1 to 8 carbon atoms), and an aralkyl group (the aryl moiety thereof has 6 to 10 carbon atoms, and the alkylene moiety thereof has 1 to 8 carbon atoms).

R^3Fand R^4Fmay be the same or different, and represent hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, an acylamino group having 2 to 8 carbon atoms, carboxyl group, an acyl group having 2 to 8 carbon atoms, an alkoxycarbonyl group (the alkoxy moiety thereof has 1 to 8 carbon atoms), or an aralkyl group (the aryl moiety thereof has 6 to 10 carbon atoms, and the alkylene moiety thereof has 1 to 8 carbon atoms),

R^5Frepresents hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkyl group having 1 to 8 carbon atoms and substituted with hydroxyl group, or an aralkyl group (the aryl moiety thereof has 6 to 10 carbon atoms, and the alkylene moiety thereof has 1 to 8 carbon atoms),

R^6Fand R^7Fmay be the same or different, and represent hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, or amino group.

X^Frepresents C or N.

Y^Frepresents N or C(═O),

provided that when X^Fis C, Y^Frepresents N, and

when X^Fis N. Y^Frepresents C(═O).

the double line consisting of the solid line and the broken line represents a single bond or a double bond,

Z^Frepresents O, S, or NH,

A^Frepresents benzene ring, pyridine ring, pyrimidine ring, pyridazine ring, thiophene ring, furan ring, pyrazole ring, imidazole ring, quinoline ring, benzimidazole ring, or indane ring which may have 1 to 4 of the same or different substituents selected from an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, and a dialkylamino group having 2 to 8 carbon atoms,

B^Frepresents O, S, NR^8F, or an atomic bond.

R^8Frepresents hydrogen atom, or an alkyl group having 1 to 8 carbon atoms.

D^Frepresents benzene ring, pyridine ring, pyrimidine ring, pyridazine ring, thiophene ring, furan ring, tetrazole ring, imidazole ring, imidazoline ring, triazole ring, thiazole ring, oxazole ring, isoxazole ring, pyrazole ring, pyrrole ring, pyrrolidine ring, piperazine ring, piperidine ring, or 5- to 8-membered cycloalkyl ring which may have 1 to 4 of the same or different substituents selected from an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, and a dialkylamino group having 2 to 8 carbon atoms.

E^Frepresents —(CR^9FR^10F)_n^F-T^F-, wherein

R^9Fand R^10Fmay be the same or different, and represent hydrogen atom, hydroxyl group, or an alkyl group having 1 to 8 carbon atoms, or R^9Fand R^10Fmay bind together to form an ethylene chain,

n^Frepresents an integer of 0 to 8, and

T^Frepresents O. S, NR^11F, or an atomic bond, wherein

R^11Frepresents hydrogen atom, or an alkyl group having 1 to 8 carbon atoms,

G^Frepresents benzene ring, pyridine ring, imidazole ring, pyrrole ring, pyrazole ring, thiophene ring, furan ring, thiazole ring, oxazole ring, pyrimidine ring, pyridazine ring, pyrazine ring, naphthalene ring, quinoline ring, quinazoline ring, indole ring, indoline ring, piperazine ring, piperidine ring, morpholine ring, or 5- to 8-membered cycloalkyl ring which may have 1 to 5 of the same or different substituents selected from an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, carbamoyl group, and methanesulfonyl group, and

m^Frepresents an integer of 0 to 2.

(F-2) A compound represented by the following general formula (IIF):

embedded image

wherein, in the formula, R^1aF. R^2aF, R^3aF, R^4aF. R^5aF, and R^6aFmay be the same or different, and represent hydrogen atom, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, an acylamino group having 2 to 8 carbon atoms, carboxyl group, an acyl group having 2 to 8 carbon atoms, an alkoxycarbonyl group (the alkoxy moiety thereof has 1 to 8 carbon atoms), a phenyl group which may have a substituent, a pyridyl group which may have a substituent, or an aralkyl group (the aryl moiety thereof has 6 to 10 carbon atoms, and the alkylene moiety thereof has 1 to 8 carbon atoms).

X^aFrepresents C or N,

Y^aFrepresents N or C(═O),

provided that when X^aFis C. Y^aFrepresents N, and

when X^aFis N, Y^aFrepresents C(O),

the double line consisting of the solid line and the broken line represents a single bond or a double bond.

A^aFrepresents benzene ring, pyridine ring, pyrimidine ring, pyridazine ring, thiophene ring, furan ring, pyrazole ring, imidazole ring, quinoline ring, benzimidazole ring, or indane ring which may have 1 to 4 of the same or different substituents selected from an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, and a dialkylamino group having 2 to 8 carbon atoms.

D^aFrepresents benzene ring, pyridine ring, pyrimidine ring, pyridazine ring, thiophene ring, furan ring, tetrazole ring, imidazole ring, imidazoline ring, triazole ring, thiazole ring, oxazole ring, isoxazole ring, pyrazole ring, pyrrole ring, pyrrolidine ring, piperazine ring, piperidine ring, or 5- to 8-membered cycloalkyl ring which may have 1 to 4 of the same or different substituents selected from an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, and a dialkylamino group having 2 to 8 carbon atoms.

E^aFrepresents —(CR^9aFR^10aF)_p^F-T^aF-, wherein

R^9aFand R^10aFare the same or different, and represent hydrogen atom, hydroxyl group, or an alkyl group having 1 to 8 carbon atoms, or R^9aFand R^10aFmay bind together to form an ethylene chain,

p^Frepresents an integer of 0 to 8, and

T^aFrepresents O. S. NR^11aF, or an atomic bond, wherein

R^11aFrepresents hydrogen atom, or an alkyl group having 1 to 8 carbon atoms, and

G^aFrepresents benzene ring, pyridine ring, imidazole ring, pyrrole ring, pyrazole ring, thiophene ring, furan ring, thiazole ring, oxazole ring, pyrimidine ring, pyridazine ring, pyrazine ring, naphthalene ring, quinoline ring, quinazoline ring, indole ring, indoline ring, piperazine ring, piperidine ring, morpholine ring, or 5- to 8-membered cycloalkyl ring which may have 1 to 5 of the same or different substituents selected from an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, an alkoxy group having 1 to 8 carbon atoms and substituted with 1 to 3 halogen atoms, a halogen atom, hydroxyl group, nitro group, cyano group, amino group, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, carbamoyl group, and methanesulfonyl group.

As for the general formulas (IF) and (IIF), examples of the alkyl group having 1 to 8 carbon atoms include methyl group, ethyl group, propyl group, isopropyl group, butyl group, i-butyl group, t-butyl group, pentyl group, hexyl group, and the like.

Examples of the 5- to 8-membered cycloalkyl ring include cyclopentyl ring, cyclohexyl ring, and the like.