Cyclic tertiary amine compound

• US 20070049620A1
• Filed: 12/12/2005
• Published: 03/01/2007
• Est. Priority Date: 06/11/2003
• Status: Abandoned Application

• Current Assignee: Sankyo Company Limited (Daiichi Sankyo Company Limited)
• Original Assignee: Sankyo Company Limited (Daiichi Sankyo Company Limited)
• Inventors: Shimozato, Takaichi, Nakao, Akira, Kimura, Tomio, Nagasaki, Takayoshi, Ohkawa, Nobuyuki
• Application Number:
  US11/301,296
• Publication Number:
  US 20070049620A1
• Time in Patent Office: Days
• US Class Current: 514/332
• CPC Class Codes: A61K 31/437 the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
• CPC Class Codes: A61K 31/444 containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
• CPC Class Codes: A61P 1/04 for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
• CPC Class Codes: A61P 1/16 for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
• CPC Class Codes: A61P 11/06 Antiasthmatics
• CPC Class Codes: A61P 13/12 of the kidneys
• CPC Class Codes: A61P 17/06 Antipsoriatics
• CPC Class Codes: A61P 19/00 Drugs for skeletal disorders
• CPC Class Codes: A61P 19/02 for joint disorders, e.g. arthritis, arthrosis
• CPC Class Codes: A61P 19/10 for osteoporosis
• CPC Class Codes: A61P 25/28 for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
• CPC Class Codes: A61P 29/00 Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
• CPC Class Codes: A61P 3/10 for hyperglycaemia, e.g. antidiabetics
• CPC Class Codes: A61P 31/04 Antibacterial agents
• CPC Class Codes: A61P 31/12 Antivirals
• CPC Class Codes: A61P 35/00 Antineoplastic agents
• CPC Class Codes: A61P 37/02 Immunomodulators
• CPC Class Codes: A61P 37/08 Antiallergic agents antiasthmatic agents A61P11/06; ophthalmic antiallergics A61P27/14
• CPC Class Codes: A61P 43/00 Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: A61P 9/10 for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
• CPC Class Codes: C07D 471/04 : Ortho-condensed systems

Abstract

A cyclic tertiary amine compound which is capable of inhibiting the production of inflammatory cytoines. The compound having a structure represented by the following formula (I):
wherein A represents an optionally substituted trivalent group which is benzene, pyrimidine, pyrrole, pyridine, pyridazine, furan, thiopene, pyrazole, imidazole, isoxazole or isothiazole; R¹ represents an aryl or a heteroaryl group, which is unsubstituted or substituted; R² represents a heteroaryl group which is unsubtituted or substituted; and R³ represents a cyclic tertiary amino group, or a pharmacologically acceptable salt of the compound.

Claims

1. A compound having a formula (I),

, wherein A represents a trivalent group selected from the group consisting of benzene, pyridine, pyridazine, pyrimidine, pyrrole, furan, thiophene, pyrazole, imidazole, isoxazole and isothiazole which is unsubstituted or substituted with one or more groups from a Substituent group δ

,

R¹ represents an aryl group which is unsubstituted or substituted with one or more groups selected from the group consisting of a Substituent group α and

a Substituent group β

;

or a heteroaryl group which is unsubstituted or substituted with one or more groups selected from the group consisting of the Substituent group a and the Substituent group β

,

R² represents a heteroaryl group which contains at least one nitrogen atom and further is unsubstituted or substituted with one or more groups selected from the group consisting of the Substituent group α and

the Substituent group β

, and

R³ represents a group having a formula (IIa) or (IIb) shown below;

, wherein

the bond including a dotted line moiety represents a single bond or a double bond,

Ring B represents a 4- to 7-membered heterocyclyl ring, said Ring B is saturated or unsaturated; and

said Ring B is optionally fused with a group selected from the group consisting of an aryl group, a heteroaryl group, a cycloalkyl group and a heterocyclyl group,

X represents a straight or branched alkylene group having from 1 to 5 carbon atoms,

Y represents a single bond or a group having formula;

C(R⁸a) (R⁸b), wherein R⁸a and R⁸b are the same or different and each represents independently a hydrogen atom, a hydroxyl group, a halogen atom, a lower alkyl group or a lower alkoxy group, or R⁸a and R⁸b together form an oxo group or a methylene group, or R⁸a and R⁸b together with the carbon atom to which they are bonded form a 3- to 6-membered cycloalkyl group,

Z represents an arylene group or a heteroarylene group,

m represents an integer of from 0 to 2,

R⁵ represents a carboxyl group, a lower alkoxycarbonyl group, an aralkyloxycarbonyl group, an aryloxycarbonyl group, a group having a formula CONR^aR^b, a group having a formula COR^c, a group having a formula SO₂NR^aR^b, a group having a formula;

SO₂R^c or a group having a formula SOR^c,

R^a and R^b are the same or different and each represents independently a hydrogen atom;

a hydroxy group;

a lower alkyl group which is unsubstituted or substituted with one or more groups selected from the Substituent group α

;

a lower alkenyl group which is unsubstituted or substituted with one or more groups from the Substituent group α

;

a lower alkynyl group which is unsubstituted or substituted with one or more groups from the Substituent group α

;

a lower alkoxy group;

a lower alkenyloxy group;

a lower alkynyloxy group;

an aralkyloxy group;

a cycloalkyl group;

a lower alkyl group substituted with a cycloalkyl group;

an aryl group;

an aralkyl group;

a heteroaryl group;

a lower alkyl group substituted with a heteroaryl group;

an amino group;

a mono-lower alkylamino group and a di-lower alkylamino group,

R^c represents a hydrogen atom, a lower alkyl group, a halogeno lower alkyl group, a lower alkoxy lower alkyl group or a hydroxy lower alkyl group,

R⁶ represents a hydrogen atom, a hydroxyl group, an amino group, a nitro group, a cyano group, a halogen atom, a lower alkyl group, a lower alkoxy group, a lower alkylthio group, a halogeno lower alkyl group, a halogeno lower alkoxy group or a halogeno lower alkylthio group,

n represents an integer of from 1 to 2, wherein in the case that n is 2, each R⁶ may be the same or different,

R⁷ represents 1 to 3 groups selected from the group consisting of a hydrogen atom, a hydroxyl group, a halogen atom, a lower alkyl group, a lower alkoxy group, a lower alkylthio group, a halogeno lower alkyl group, a halogeno lower alkoxy group and a halogeno lower alkylthio group,

the Substituent group α

is selected from the group consisting of a hydroxyl group, a nitro group, a cyano group, a halogen atom, a lower alkoxy group, a halogeno lower alkoxy group, a carboxyl group, a lower alkoxycarbonyl group, a carbamoyl group, a lower acyloxy group, a lower alkylthio group, a halogeno lower alkylthio group and a group having a formula —

NR^dR^e, wherein R^d and R^e are the same or different and each represents independently a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, an aralkyl group, a lower alkylsulfonyl group or a lower alkylcarbonyl group, or R^d and R^e together with the nitrogen atom to which they are bonded form a heterocyclyl group,

the Substituent group β

is selected from the group consisting of a lower alkyl group which is unsubstituted or substituted with one or more groups from the Substituent group α

;

a lower alkenyl group which is unsubstituted or substituted with one or more groups from the Substituent group α

;

a lower alkynyl group which is unsubstituted or substituted with one or more groups from the Substituent group α

;

an aralkyl group and a cycloalkyl group,

the Substituent group γ

is selected from the group consisting of an oxo group, a hydroxyimino group, a lower alkoxyimino group, a lower alkylene group, a lower alkylenedioxy group, a lower alkylsulfinyl group and a lower alkylsulfonyl group,

the Substituent group δ

is selected from the group consisting of a group from the Substituent group β

;

a cycloalkyl group substituted with one or more groups selected from the group consisting of the Substituent group α

, the Substituent group β and

the Substituent group γ

;

an aryl group which is unsubstituted or substituted with one or more groups selected from the group consisting of the Substituent group α

, the Substituent group β and

the Substituent group γ

;

a heteroaryl group which is unsubstituted or substituted with one or more groups selected from the group consisting of the Substituent group α

, the Substituent group β and

the Substituent group γ

; and

a heterocyclyl group which is unsubstituted or substituted with one or more groups selected from the group consisting of the Substituent group α

, the Substituent group β and

the Substituent group γ

,

or a pharmacologically acceptable salt thereof,

PROVIDED THAT each of the atoms of the Ring A to which R¹ and R³ are bonded is adjacent to the atom of the Ring A to which R² is bonded.

2. The compound according to claim 1, wherein A is a trivalent group selected from the group consisting of a pyrrole group which is unsubstituted or substituted with two groups from the Substituent group δ

and a pyrazole group which is unsubstituted or substituted with one group from the Substituent group δ

, or a pharmacologically acceptable salt thereof.

3. The compound according to claim 1, wherein A is a pyrrole group which is unsubstituted or substituted with two groups from the Substituent group δ

, or a pharmacologically acceptable salt thereof.

4. The compound according to claim 1, wherein A is a pyrrole group, or a pharmacologically acceptable salt thereof.

5. The compound according to claim 1, wherein R¹ is an aryl group which is unsubstituted or substituted with one or more groups selected from the group consisting of the Substituent group α

and the Substituent group β

, or a pharmacologically acceptable salt thereof.

6. The compound according to claim 1, wherein R¹ is a phenyl group or a naphthyl group which is unsubstituted or substituted with one or more groups selected from the group consisting of the Substituent group α

and the Substituent group β

, or a pharmacologically acceptable salt thereof.

7. The compound according to claim 1, wherein R¹ is a phenyl group which is unsubstituted or substituted with one or more groups selected from the group consisting of a Substituent group α

¹ and a Substituent group β

¹,

the Substituent group α

¹ is selected from the group consisting of a hydroxyl group, a cyano group, a halogen atom, a lower alkoxy group and a halogeno lower alkoxy group; and

the Substituent group β

¹ is selected from the group consisting of a lower alkyl group, a halogeno lower alkyl group and a hydroxy lower alkyl group, or a pharmacologically acceptable salt thereof.

8. The compound according to claim 1, wherein R¹ is an unsubstituted phenyl group or a phenyl group which is substituted with one or more groups selected from the group consisting of a hydroxyl group, a cyano group, a halogen atom, a lower alkoxy group, a halogeno lower alkyl group and a halogeno lower alkoxy group, or a pharmacologically acceptable salt thereof.

9. The compound according to claim 1, wherein R¹ is a phenyl, 3-cyanophenyl, 4-fluorophenyl, 3-fluorophenyl, 4-chlorophenyl, 3-chlorophenyl, 2,4-difluorophenyl, 3,4-difluorophenyl, 3,4-dichlorophenyl, 3,4,5-trifluorophenyl, 3-chloro-4-fluorophenyl, 3-methoxyphenyl, 3-difluoromethoxyphenyl, 3-trifluoromethoxyphenyl, 3-trifluoromethylphenyl or 4-fluoro-3-methoxyphenyl group, or a pharmacologically acceptable salt thereof.

10. The compound according to claim 1, wherein R¹ is a phenyl, 3-cyanophenyl, 4-fluorophenyl, 3-fluorophenyl, 3-chlorophenyl, 3,4-difluorophenyl, 3,4,5-trifluorophenyl, 3-chloro-4-fluorophenyl, 3-methoxyphenyl, 3-difluoromethoxyphenyl, 3-trifluoromethylphenyl or 4-fluoro-3-methoxyphenyl, or a pharmacologically acceptable salt thereof.

11. The compound according to claim 1, wherein R¹ is a phenyl, 4-fluorophenyl, 3-fluorophenyl, 3-chlorophenyl, 3,4-difluorophenyl, 3-chloro-4-fluorophenyl or 3-trifluoromethylphenyl group, or a pharmacologically acceptable salt thereof.

12. The compound according to claim 1, wherein R² is a 5- to 6-membered heteroaryl group which contains one or two nitrogen atoms and is unsubstituted or substituted with one or more groups selected from the group consisting of the Substituent group α

and the Substituent group β

, or a pharmacologically acceptable salt thereof.

13. The compound according to claim 1, wherein R² is a pyridyl group or a pyrimidinyl group which is unsubstituted or substituted with one or more groups selected from the group consisting of the Substituent group α

and the Substituent group β

, or a pharmacologically acceptable salt thereof.

14. The compound according to claim 1, wherein R² is a 4-pyridyl group or a 4-pyrimidinyl group which is unsubstituted or substituted with one or more groups selected from the group consisting of the Substituent group α

and the Substituent group β

, or a pharmacologically acceptable salt thereof.

15. The compound according to claim 1, wherein R² is a 4-pyridyl group or a 4-pyrimidinyl group, of which the 2-position is unsubstituted or substituted with one group selected from the group consisting of the Substituent group α

and the Substituent group β

, or a pharmacologically acceptable salt thereof.

16. The compound according to claim 1, wherein R² is a 4-pyridyl group or a 4-pyrimidinyl group, of which the 2-position is unsubstituted or substituted with one group selected from the group consisting of a methoxy, amino, methylamino, benzylamino and α

-methylbenzylamino group, or a pharmacologically acceptable salt thereof.

17. The compound according to claim 1, wherein m is 1, or a pharmacologically acceptable salt thereof.

18. The compound according to claim 1, wherein R³ is a group having the formula (IIa);

X is an alkylene group having from 1 to 4 carbon atoms;

Y is a group having the formula C(R⁸a)(R⁸b), wherein R⁸a and R⁸b are the same or different and each represents independently a hydrogen atom, a hydroxyl group, a halogen atom, an alkyl group having from 1 to 4 carbon atoms or an alkoxy group having from 1 to 4 carbon atoms, or R⁸a and R⁸b together form an oxo group or methylene group, or R⁸a and R⁸b together with the carbon atom to which they are bonded form a 3- to 6-membered cycloalkyl group, or a pharmacologically acceptable salt thereof.

19. The compound according to claim 1, wherein R³ is a group having the formula (IIa);

X is a methylene group; and

Y is a group having the formula C(R⁸a)(R⁸b), wherein R⁸a and R⁸b are the same or different and each represents independently a hydrogen atom, a hydroxyl group, a fluorine atom, a methyl group, an ethyl group, a methoxy group or an ethoxy group, or R⁸a and R⁸b together form an oxo group or a methylene group, or R⁸a and R⁸b together with the carbon atom to which they are bonded form a cyclopropyl group, or a pharmacologically acceptable salt thereof.

20. The compound according to claim 1, wherein R³ is a group having the formula (IIa);

X is a methylene group; and

Y is a group having the formula C(R⁸a)(R⁸b), wherein R⁸a and R⁸b are the same or different and each represents independently a hydrogen atom, a fluorine atom, a methyl group, a hydroxyl group or an oxo group, or a pharmacologically acceptable salt thereof.

21. The compound according to claim 1, wherein R³ is a group having the formula (IIa);

X is a methylene group; and

Y is a group having the formula CH₂, or a pharmacologically acceptable salt thereof.

22. The compound according to claim 1, wherein R³ is a group having the formula (IIb);

and the Ring B is a 5- or 6-membered heterocyclyl ring which contains one nitrogen atom and optionally contains one atom or a group selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a group having a formula ═

SO and a group having a formula ═

SO₂, said Ring B is saturated or unsaturated, and optionally is fused with an aryl group, a heteroaryl group, a cycloalkyl group or a heterocyclyl group, or a pharmacologically acceptable salt thereof.

23. The compound according to claim 1, wherein R³ is a group having the formula (IIb);

and the Ring B is a 5- or 6-membered heterocyclyl ring which contains one nitrogen atom, said Ring B is saturated or unsaturated, and optionally is fused with an aryl group, a heteroaryl group, a cycloalkyl group or a heterocyclyl group, or a pharmacologically acceptable salt thereof.

24. The compound according to claim 1, wherein R³ is a group having the formula (IIb);

and the Ring B is a pyrrolidine or pyrroline group, or a pharmacologically acceptable salt thereof.

25. The compound according to claim 1, wherein Z is a phenylene group, a thiophenediyl group, a furandiyl group, a pyrrolediyl group, an oxazolediyl group, a thiazolediyl group, a thiadiazolediyl group or a pyridinediyl group, or a pharmacologically acceptable salt thereof.

26. The compound according to claim 1, wherein Z is a phenylene group or a thiophenediyl group, or a pharmacologically acceptable salt thereof.

27. The compound according to claim 1, wherein R⁵ is a group having the formula CONR^aR^b, a group having the formula COR^c, a group having the formula SO₂NR^aR^b, a group having the formula SO₂R^c or a group having the formula SOR^c, wherein R^a and R^b are the same or different and each is independently a hydrogen atom, a lower alkyl group which is unsubstituted or substituted with one or more groups selected from the group consisting of the Substituent group α

, a lower alkoxy group, a lower alkenyloxy group, a cycloalkyl group, an amino group, a mono-lower alkylamino group and a di-lower alkylamino group; and

R^c is a lower alkyl group, or a pharmacologically acceptable salt thereof.

28. The compound according to claim 1, wherein R⁵ is a group having the formula CONR^aR^b, a group having the formula SO₂NR^aR^b, a group having the formula SO₂R^c or a group having the formula SOR^c, wherein R^a and R^b are the same or different and each is independently a hydrogen atom, a lower alkyl group, a halogeno lower alkyl group, a hydroxy lower alkyl group, a lower alkoxy lower alkyl group, a lower alkoxy group or a cycloalkyl group;

and R^c is a lower alkyl group, or a pharmacologically acceptable salt thereof.

29. The compound according to claim 1, wherein R⁵ is a carbamoyl, N-methylcarbamoyl, N-ethylcarbamoyl, N-propylcarbamoyl, N-isopropylcarbamoyl, N-cyclopropylcarbamoyl, N-cyclopentylcarbamoyl, N-(2-fluoroethyl)carbamoyl, N-(2-methoxyethyl)carbamoyl, N-methylsulfamoyl, N-ethylsulfamoyl, N-propylsulfamoyl, N-isopropylsulfamoyl, N-cyclopropylsulfamoyl, N-cyclopentylsulfamoyl, N-(2-fluoroethyl)sulfamoyl, N-(methoxyethyl)sulfamoyl, N-methoxysulfamoyl, methanesulfonyl, ethanesulfonyl, propanesulfonyl, methanesulfinyl, ethanesulfinyl or propanesulfinyl group, or a pharmacologically acceptable salt thereof.

30. The compound according to claim 1, wherein R⁶ is a hydrogen atom, a fluorine atom or a methoxy group, or a pharmacologically acceptable salt thereof.

31. The compound according to claim 1, wherein R⁶ is a hydrogen atom, or a pharmacologically acceptable salt thereof.

32. The compound according to claim 1, wherein R⁷ is 1 or 2 groups selected from the group consisting of a hydrogen atom, a hydroxyl group and a lower alkyl group, or a pharmacologically acceptable salt thereof.

33. The compound according to claim 1, wherein R⁷ is a hydrogen atom, or a pharmacologically acceptable salt thereof.

34. The compound according to claim 1, wherein the compound having the formula (I) is a compound having one of the following formulae:

, wherein R⁴ and R^4′

are the same or different and each represents independently a hydrogen atom or a group from the Substituent group δ

, or a pharmacologically acceptable salt thereof.

35. The compound according to claim 1, wherein the compound having the formula (I) is a compound having either one of the following formulae:

, wherein R⁴ and R^4′

are the same or different and each represents independently a hydrogen atom or a group selected from the Substituent group δ

, or a pharmacologically acceptable salt thereof.

36. The compound according to claim 1, wherein the compound is selected from the the group consisting of:

4-[1-(4-carbamoylphenethyl)-1,2,3,6-tetrahydropyridin-4-yl]-2-(4-fluorophenyl)-3-(pyridin-4-yl)-1H-pyrrole,

3-[1-(4-carbamoylphenethyl)-1,2,3,6-tetrahydropyridin-4-yl]-5-(4-fluorophenyl)-4-(pyridin-4-yl)-1H-pyrazole,

2-(4-fluorophenyl)-4-[1-[4-(N-methylcarbamoyl)phenethyl]-1,2,3,6-tetrahydropyridin-4-yl]-3-(pyridin-4-yl)-1H-pyrrole,

4-[1-[4-(N-ethylcarbamoyl)phenethyl]-1,2,3,6-tetrahydropyridin-4-yl]-2-(4-fluorophenyl)-3-(pyridin-4-yl)-1H-pyrrole,

4-[1-[4-(N-cyclopropylcarbamoyl)phenethyl]-1,2,3,6-tetrahydropyridin-4-yl]-2-(4-fluorophenyl)-3-(pyridin-4-yl)-1H-pyrrole,

2-(4-fluorophenyl)-4-[1-[4-(N-isopropylcarbamoyl)phenethyl]-1,2,3,6-tetrahydropyridin-4-yl]-3-(pyridin-4-yl)-1H-pyrrole,

2-(4-fluorophenyl)-4-[1-[4-(N-propylcarbamoyl)phenethyl]-1,2,3,6-tetrahydropyridin-4-yl]-3-(pyridin-4-yl)-1H-pyrrole,

4-[1-[4-[N-(2-fluoroethyl)carbamoyl]phenethyl]-1,2,3,6-tetrahydropyridin-4-yl]-2-(4-fluorophenyl)-3-(pyridin-4-yl)-1H-pyrrole,

4-[1-[4-(N-cyclopentylcarbamoyl)phenethyl]-1,2,3,6-tetrahydropyridin-4-yl]-2-(4-fluorophenyl)-3-(pyridin-4-yl)-1H-pyrrole,

4-[1-[4-[N-(ethoxycarbonylmethyl)carbamoyl]phenethyl]-1,2,3,6-tetrahydropyridin-4-yl]-2-(4-fluorophenyl)-3-(pyridin-4-yl)-1H-pyrrole,

2-(4-fluorophenyl)-4-[1-[4-(N-methylsulfamoyl)phenethyl]-1,2,3,6-tetrahydropyridin-4-yl]-3-(pyridin-4-yl)-1H-pyrrole,

4-[1-[4-(N-ethylsulfamoyl)phenethyl]-1,2,3,6-tetrahydropyridin-4-yl]-2-(4-fluorophenyl)-3-(pyridin-4-yl)-1H-pyrrole,

2-(4-fluorophenyl)-4-[1-[4-(N-propylsulfamoyl)phenethyl]-1,2,3,6-tetrahydropyridin-4-yl]-3-(pyridin-4-yl)-1H-pyrrole,

2-(4-fluorophenyl)-4-[1-[4-(N-isopropylsulfamoyl)phenethyl]-1,2,3,6-tetrahydropyridin-4-yl]-3-(pyridin-4-yl)-1H-pyrrole,

2-(3-chloro-4-fluorophenyl)-4-[1-[4-(N-methylsulfamoyl)phenethyl]-1,2,3,6-tetrahydropyridin-4-yl]-3-(pyridin-4-yl)-1H-pyrrole,

4-[1-[4-(N-cyclopropylsulfamoyl)phenethyl]-1,2,3,6-tetrahydropyridin-4-yl]-2-(4-fluorophenyl)-3-(pyridin-4-yl)-1H-pyrrole,

4-[1-[4-[N-(2-fluoroethyl)sulfamoyl]phenethyl]-1,2,3,6-tetrahydropyridin-4-yl]-2-(4-fluorophenyl)-3-(pyridin-4-yl)-1H-pyrrole,

4-[1-[4-(N,N-dimethylsulfamoyl)phenethyl]-1,2,3,6-tetrahydropyridin-4-yl]-2-(4-fluorophenyl)-3-(pyridin-4-yl)-1H-pyrrole,

2-(4-fluorophenyl)-4-[1-[4-[N-(2-methoxyethyl)sulfamoyl]phenethyl]-1,2,3,6-tetrahydropyridin-4-yl]-3-(pyridin-4-yl)-1H-pyrrole,

4-[1-[4-(N-ethoxysulfamoyl)phenethyl]-1,2,3,6-tetrahydropyridin-4-yl]-2-(4-fluorophenyl)-3-(pyridin-4-yl)-1H-pyrrole,

4-[1-[4-(N-allyloxysulfamoyl)phenethyl)-1,2,3,6-tetrahydropyridin-4-yl]-2-(4-fluorophenyl)-3-(pyridin-4-yl)-1H-pyrrole,

2-(4-fluorophenyl)-4-[1-(4-methanesulfonylphenethyl]-1,2,3,6-tetrahydropyridin-4-yl]-3-(pyridin-4-yl)-1H-pyrrole,

2-(3-chloro-4-fluorophenyl)-4-[1-(4-methanesulfonyl)phenethyl]-1,2,3,6-tetrahydropyridin-4-yl]-3-(pyridin-4-yl)-1H-pyrrole,

2-(4-fluorophenyl)-4-[1-(4-methanesulfinylphenethyl)-1,2,3,6-tetrahydropyridin-4-yl]-3-(pyridin-4-yl)-1H-pyrrole,

2-(3-chloro-4-fluorophenyl)-4-[1-(4-methanesulfinylphenethyl)-1,2,3,6-tetrahydropyridin-4-yl]-3-(pyridin-4-yl)-1H-pyrrole,

4-[1-(4-acetylphenethyl)-1,2,3,6-tetrahydropyridin-4-yl]-2-(3-chloro-4-fluorophenyl)-3-(pyridin-4-yl)-1H-pyrrole,

2-(3-chloro-4-fluorophenyl)-4-[(2S,8aS)-2-[4-(N-methylcarbamoyl)phenyl]-1,2,3,5,6,8a-hexahydroindolidin-7-yl]-3-(pyridin-4-yl)-1H-pyrrole,

4-[(2S,8aS)-2-(4-carbamoylphenyl)-1,2,3,5,6,8a-hexahydroindolidin-7-yl]-2-(4-fluorophenyl)-3-(pyridin-4-yl)-1H-pyrrole,

2-(4-fluorophenyl)-4-[(2S,8aS)-2-[4-(N-methylcarbamoyl)phenyl]-1,2,3,5,6,8a-hexahydroindolidin-7-yl]-3-(pyridin-4-yl)-1H-pyrrole,

4-[(2S,8aS)-2-[4-(N-ethylcarbamoyl)phenyl]-1,2,3,5,6,8a-hexahydroindolidin-7-yl]-2-(4-fluorophenyl)-3-(pyridin-4-yl)-1H-pyrrole,

4-[(2S,8aS)-2-[4-(N-benzylcarbamoyl)phenyl]-1,2,3,5,6,8a-hexahydroindolidin-7-yl]-2-(4-fluorophenyl)-3-(pyridin-4-yl)-1H-pyrrole,

4-[(2S,8aS)-2-[4-(N-cyclopropylcarbamoyl)phenyl]-1,2,3,5,6,8a-hexahydroindolidin-7-yl]-2-(4-fluorophenyl)-3-(pyridin-4-yl)-1H-pyrrole,

4-[(2S,8aS)-2-[4-[N-(2-fluoroethyl)carbamoyl]phenyl]-1,2,3,5,6,8a-hexahydroindolidin-7-yl]-2-(4-fluorophenyl)-3-(pyridin-4-yl)-1H-pyrrole,

2-(4-fluorophenyl)-4-[(2S,8aS)-2-[4-(N-propylcarbamoyl)phenyl]-1,2,3,5,6,8a-hexahydroindolidin-7-yl]-3-(pyridin-4-yl)-1H-pyrrole,

2-(4-fluorophenyl)-4-[(2S,8aS)-2-[4-(N-isopropylcarbamoyl)phenyl]-1,2,3,5,6,8a-hexahydroindolidin-7-yl]-3-(pyridin-4-yl)-1H-pyrrole,

2-(4-fluorophenyl)-4-[(2S,8aS)-2-[4-[N-(2-methoxyethyl)carbamoyl]phenyl]-1,2,3,5,6,8a-hexahydroindolidin-7-yl]-3-(pyridin-4-yl)-1H-pyrrole,

2-(4-fluorophenyl)-4-[1-[4-(2-methoxyethyl)sulfonylphenethyl]-1,2,3,6-tetrahydropyridin-4-yl]-3-(pyridin-4-yl)-1H-pyrrole,

2-(4-fluorophenyl)-4-[1-[4-(2-hydroxyethyl)sulfonylphenethyl]-1,2,3,5,6-tetrahydropyridin-4-yl]-3-(pyridin-4-yl)-1H-pyrrole,

2-(3-chloro-4-fluorophenyl)-4-[1-[4-(2-methoxyethyl)sulfonylphenethyl]-1,2,3,6-tetrahydropyridin-4-yl]-3-(pyridin-4-yl)-1H-pyrrole, and

2-(3-chloro-4-fluorophenyl)-4-[1-[4-(2-hydroxyethyl)sulfonylphenethyl]-1,2,3,6-tetrahydropyridin-4-yl]-3-(pyridin-4-yl)-1H-pyrrole,

or a pharmaceutically acceptable salt thereof

37. The compound according to claim 1, wherein A is a trivalent group selected from the group consisting of a pyrrole group which is unsubstituted or substituted with two groups from the Substituent group δ

and a pyrazole group which is unsubstituted or substituted with one group from the Substituent group δ

;

R¹ is a phenyl group or a naphthyl group which is unsubstituted or substituted with one or more groups selected from the group consisting of the Substituent group a and the Substituent group β

;

R² is a 5- to 6-membered heteroaryl group which contains one or two nitrogen atoms and is unsubstituted or substituted with one or more groups selected from the group consisting of the Substituent group α and

the Substituent group β

;

m is 1;

R³ is a group having the formula (IIa);

X is an alkylene group having from 1 to 4 carbon atoms;

Y is a group having the formula C(R⁸a)(R⁸b), wherein R⁸a and R⁸b are the same or different and each represents independently a hydrogen atom, a hydroxyl group, a halogen atom, an alkyl group having from 1 to 4 carbon atoms or an alkoxy group having from 1 to 4 carbon atoms, or R⁸a and R⁸b together form an oxo group or methylene group, or R⁸a and R⁸b together with the carbon atom to which they are bonded form a 3- to 6-membered cycloalkyl group;

Z is a phenylene group, a thiophenediyl group, a furandiyl group, a pyrrolediyl group, an oxazolediyl group, a thiazolediyl group, a thiadiazolediyl group or a pyridinediyl group;

R⁵ is a group having the formula CONR^aR^b, a group having the formula COR^c, a group having the formula SO₂NR^aR^b, a group having the formula SO₂R^c or a group having the formula SOR^c, wherein R^a and R^b are the same or different and each is independently a hydrogen atom, a lower alkyl group which is unsubstituted or substituted with one or more groups selected from the group consisting of the Substituent group α

, a lower alkoxy group, a lower alkenyloxy group, a cycloalkyl group, an amino group, a mono-lower alkylamino group and a di-lower alkylamino group; and

R^c is a lower alkyl group;

R⁶ is a hydrogen atom, a fluorine atom or a methoxy group; and

R⁷ is 1 or 2 groups selected from the group consisting of a hydrogen atom, a hydroxyl group and a lower alkyl group,

or a pharmacologically acceptable salt thereof.

38. The compound according to claim 1, wherein A is a pyrrole group which is unsubstituted or substituted with two groups from the Substituent group δ

;

R¹ is a phenyl group which is unsubstituted or substituted with one or more groups selected from the group consisting of a Substituent group α

¹ and a Substituent group β

¹,

the Substituent group α

¹ is selected from the group consisting of a hydroxyl group, a cyano group, a halogen atom, a lower alkoxy group and a halogeno lower alkoxy group; and

the Substituent group β

¹ is selected from the group consisting of a lower alkyl group;

R² is a pyridyl group or a pyrimidinyl group which is unsubstituted or substituted with one or more groups selected from the group consisting of the Substituent group a and the Substituent group β

;

m is 1;

R³ is a group having the formula (IIa);

X is a methylene group; and

Y is a group having the formula C(R⁸a)(R⁸b), wherein R⁸a and R⁸b are the same or different and each represents independently a hydrogen atom, a hydroxyl group, a fluorine atom, a methyl group, an ethyl group, a methoxy group or an ethoxy group, or R⁸a and R⁸b together form an oxo group or a methylene group, or R⁸a and R⁸b together with the carbon atom to which they are bonded form a cyclopropyl group;

Z is a phenylene group, a thiophenediyl group, a furandiyl group, a pyrrolediyl group, an oxazolediyl group, a thiazolediyl group, a thiadiazolediyl group or a pyridinediyl group;

R⁵ is a group having the formula CONR^aR^b, a group having the formula COR^c, a group having the formula SO₂NR^aR^b, a group having the formula SO₂R^c or a group having the formula SOR^c, wherein R^a and R^b are the same or different and each is independently a hydrogen atom, a lower alkyl group which is unsubstituted or substituted with one or more groups selected from the group consisting of the Substituent group α

, a lower alkoxy group, a lower alkenyloxy group, a cycloalkyl group, an amino group, a mono-lower alkylamino group and a di-lower alkylamino group; and

R^c is a lower alkyl group;

R⁶ is a hydrogen atom, a fluorine atom or a methoxy group; and

R⁷ is 1 or 2 groups selected from the group consisting of a hydrogen atom, a hydroxyl group and a lower alkyl group,

or a pharmacologically acceptable salt thereof.

39. The compound according to claim 1, wherein A is a pyrrole group which is unsubstituted or substituted with two groups from the Substituent group δ

;

R¹ is an unsubstituted phenyl group or a phenyl group which is substituted with one or more groups selected from the group consisting of a hydroxyl group, a cyano group, a halogen atom, a lower alkoxy group, a halogeno lower alkyl group and a halogeno lower alkoxy group;

R² is a 4-pyridyl group or a 4-pyrimidinyl group which is unsubstituted or substituted with one or more groups selected from the group consisting of the Substituent group a and the Substituent group β

;

m is 1;

R³ is a group having the formula (IIa);

X is a methylene group; and

Y is a group having the formula C(R⁸a)(R⁸b), wherein R⁸a and R⁸b are the same or different and each represents independently a hydrogen atom, a hydroxyl group, a fluorine atom, a methyl group, an ethyl group, a methoxy group or an ethoxy group, or R⁸a and R⁸b together form an oxo group or a methylene group, or R⁸a and R⁸b together with the carbon atom to which they are bonded form a cyclopropyl group;

Z is a phenylene group or a thiophenediyl group;

R⁵ is a group having the formula CONR^aR^b, a group having the formula COR^c, a group having the formula SO₂NR^aR^b, a group having the formula SO₂R^c or a group having the formula SOR^c, wherein R^a and R^b are the same or different and each is independently a hydrogen atom, a lower alkyl group which is unsubstituted or substituted with one or more groups selected from the group consisting of the Substituent group α

, a lower alkoxy group, a lower alkenyloxy group, a cycloalkyl group, an amino group, a mono-lower alkylamino group and a di-lower alkylamino group; and

R^c is a lower alkyl group

R⁶ is a hydrogen atom, a fluorine atom or a methoxy group;

R⁷ is 1 or 2 groups selected from the group consisting of a hydrogen atom, a hydroxyl group and a lower alkyl group,

or a pharmacologically acceptable salt thereof.

40. The compound according to claim 1, wherein A is a pyrrole group which is unsubstituted or substituted with two groups from the Substituent group δ

;

R¹ is a phenyl, 3-cyanophenyl, 4-fluorophenyl, 3-fluorophenyl, 4-chlorophenyl, 3-chlorophenyl, 2,4-difluorophenyl, 3,4-difluorophenyl, 3,4-dichlorophenyl, 3,4,5-trifluorophenyl, 3-chloro-4-fluorophenyl, 3-methoxyphenyl, 3-difluoromethoxyphenyl, 3-trifluoromethoxyphenyl, 3-trifluoromethylphenyl or 4-fluoro-3-methoxyphenyl group;

R² is a 4-pyridyl group or a 4-pyrimidinyl group, of which the 2-position is unsubstituted or substituted with one group selected from the group consisting of the Substituent group a and the Substituent group β

;

m is 1;

R³ is a group having the formula (IIa);

X is a methylene group; and

Y is a group having the formula C(R⁸a)(R⁸b), wherein R⁸a and R⁸b are the same or different and each represents independently a hydrogen atom, a fluorine atom, a methyl group, a hydroxyl group or an oxo group;

Z is a phenylene group or a thiophenediyl group;

R⁵ is a carbamoyl, N-methylcarbamoyl, N-ethylcarbamoyl, N-propylcarbamoyl, N-isopropylcarbamoyl, N-cyclopropylcarbamoyl, N-cyclopentylcarbamoyl, N-(2-fluoroethyl)carbamoyl, N-(2-methoxyethyl)carbamoyl, N-methylsulfamoyl, N-ethylsulfamoyl, N-propylsulfamoyl, N-isopropylsulfamoyl, N-cyclopropylsulfamoyl, N-cyclopentylsulfamoyl, N-(2-fluoroethyl)sulfamoyl, N-(methoxyethyl)sulfamoyl, N-methoxysulfamoyl, methanesulfonyl, ethanesulfonyl, propanesulfonyl, methanesulfinyl, ethanesulfinyl or propanesulfinyl group;

R⁶ is a hydrogen atom, a fluorine atom or a methoxy group; and

R⁷ is 1 or 2 groups selected from the group consisting of a hydrogen atom, a hydroxyl group and a lower alkyl group,

or a pharmacologically acceptable salt thereof.

41. The compound according to claim 1, wherein A is a pyrrole group;

R¹ is a phenyl, 4-fluorophenyl, 3-fluorophenyl, 3-chlorophenyl, 3,4-difluorophenyl, 3-chloro-4-fluorophenyl or 3-trifluoromethylphenyl group;

R² is a 4-pyridyl group or a 4-pyrimidinyl group, of which the 2-position is unsubstituted or substituted with one group selected from the group consisting of a methoxy, amino, methylamino, benzylamino and α

-methylbenzylamino group;

m is 1;

R³ is a group having the formula (IIa);

X is a methylene group; and

Y is a group having the formula CH₂;

Z is a phenylene group or a thiophenediyl group;

R⁵ is a carbamoyl, N-methylcarbamoyl, N-ethylcarbamoyl, N-propylcarbamoyl, N-isopropylcarbamoyl, N-cyclopropylcarbamoyl, N-cyclopentylcarbamoyl, N-(2-fluoroethyl)carbamoyl, N-(2-methoxyethyl)carbamoyl, N-methylsulfamoyl, N-ethylsulfamoyl, N-propylsulfamoyl, N-isopropylsulfamoyl, N-cyclopropylsulfamoyl, N-cyclopentylsulfamoyl, N-(2-fluoroethyl)sulfamoyl, N-(methoxyethyl)sulfamoyl, N-methoxysulfamoyl, methanesulfonyl, ethanesulfonyl, propanesulfonyl, methanesulfinyl, ethanesulfinyl or propanesulfinyl group;

R⁶ is a hydrogen atom;

R⁷ is a hydrogen atom, R⁷ is a hydrogen atom,

or a pharmacologically acceptable salt thereof.

42. The compound according to any one of claims 37 to 41, wherein the compound having the formula (I) is a compound having one of the following formulae:

, wherein R⁴ and R^4′

are the same or different and each represents independently a hydrogen atom or a group from the Substituent group δ

, or a pharmacologically acceptable salt thereof.

43. The compound according to any one of claims 37 to 41, wherein the compound having the formula (I) is a compound having either one of the following formulae:

, wherein R⁴ and R^4′

are the same or different and each represents independently a hydrogen atom or a group selected from the Substituent group δ

, or a pharmacologically acceptable salt thereof.

44. The compound according to claim 1, wherein A is a trivalent group selected from the group consisting of a pyrrole group which is unsubstituted or substituted with two groups from the Substituent group δ

and a pyrazole group which is unsubstituted or substituted with one group from the Substituent group δ

;

R¹ is a phenyl group or a naphthyl group which is unsubstituted or substituted with one or more groups selected from the group consisting of the Substituent group α and

the Substituent group β

;

R² is a 5- to 6-membered heteroaryl group which contains one or two nitrogen atoms and is unsubstituted or substituted with one or more groups selected from the group consisting of the Substituent group α and

the Substituent group β

;

m is 1;

R³ is a group having the formula (IIb); and

the Ring B is a 5- or 6-membered heterocyclyl ring which contains one nitrogen atom and optionally contains one atom or a group selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a group having a formula ═

SO and a group having a formula ═

SO₂, said Ring B is saturated or unsaturated, and optionally is fused with an aryl group, a heteroaryl group, a cycloalkyl group or a heterocyclyl group;

Z is a phenylene group, a thiophenediyl group, a furandiyl group, a pyrrolediyl group, an oxazolediyl group, a thiazolediyl group, a thiadiazolediyl group or a pyridinediyl group;

R⁵ is a group having the formula CONR^aR^b, a group having the formula COR^c, a group having the formula SO₂NR^aR^b, a group having the formula SO₂R^c or a group having the formula SOR^c, wherein R^a and R^b are the same or different and each is independently a hydrogen atom, a lower alkyl group which is unsubstituted or substituted with one or more groups selected from the group consisting of the Substituent group α

, a lower alkoxy group, a lower alkenyloxy group, a cycloalkyl group, an amino group, a mono-lower alkylamino group and a di-lower alkylamino group; and

R^c is a lower alkyl group;

R⁶ is a hydrogen atom, a fluorine atom or a methoxy group; and

R⁷ is 1 or 2 groups selected from the group consisting of a hydrogen atom, a hydroxyl group and a lower alkyl group,

or a pharmacologically acceptable salt thereof.

45. The compound according to claim 1, wherein A is a trivalent group selected from the group consisting of a pyrrole group which is unsubstituted or substituted with two groups from the Substituent group δ

and a pyrazole group which is unsubstituted or substituted with one group from the Substituent group δ

;

R¹ is a phenyl group which is unsubstituted or substituted with one or more groups selected from the group consisting of a Substituent group α

¹ and a Substituent group β

¹,

the Substituent group α

¹ is selected from the group consisting of a hydroxyl group, a cyano group, a halogen atom, a lower alkoxy group and a halogeno lower alkoxy group; and

the Substituent group β

¹ is selected from the group consisting of a lower alkyl group;

R² is a pyridyl group or a pyrimidinyl group which is unsubstituted or substituted with one or more groups selected from the group consisting of the Substituent group a and the Substituent group β

;

m is 1;

R³ is a group having the formula (IIb); and

the Ring B is a 5- or 6-membered heterocyclyl ring which contains one nitrogen atom, said Ring B is saturated or unsaturated, and optionally is fused with an aryl group, a heteroaryl group, a cycloalkyl group or a heterocyclyl group;

Z is a phenylene group, a thiophenediyl group, a furandiyl group, a pyrrolediyl group, an oxazolediyl group, a thiazolediyl group, a thiadiazolediyl group or a pyridinediyl group;

R⁵ is a group having the formula CONR^aR^b, a group having the formula COR^c, a group having the formula SO₂NR^aR^b, a group having the formula SO₂R^c or a group having the formula SOR^c, wherein R^a and R^b are the same or different and each is independently a hydrogen atom, a lower alkyl group which is unsubstituted or substituted with one or more groups selected from the group consisting of the Substituent group α

, a lower alkoxy group, a lower alkenyloxy group, a cycloalkyl group, an amino group, a mono-lower alkylamino group and a di-lower alkylamino group; and

R^c is a lower alkyl group;

R⁶ is a hydrogen atom, a fluorine atom or a methoxy group; and

R⁷ is 1 or 2 groups selected from the group consisting of a hydrogen atom, a hydroxyl group and a lower alkyl group,

or a pharmacologically acceptable salt thereof.

46. The compound according to claim 1, wherein A is a pyrrole group which is unsubstituted or substituted with two groups from the Substituent group δ

;

R¹ is an unsubstituted phenyl group or a phenyl group which is substituted with one or more groups selected from the group consisting of a hydroxyl group, a cyano group, a halogen atom, a lower alkoxy group, a halogeno lower alkyl group and a halogeno lower alkoxy group;

R² is a 4-pyridyl group or a 4-pyrimidinyl group which is unsubstituted or substituted with one or more groups selected from the group consisting of the Substituent group α and

the Substituent group β

;

m is 1;

R³ is a group having the formula (IIb); and

the Ring B is a pyrrolidine or pyrroline group;

Z is a phenylene group, a thiophenediyl group, a furandiyl group, a pyrrolediyl group, an oxazolediyl group, a thiazolediyl group, a thiadiazolediyl group or a pyridinediyl group;

R⁵ is a group having the formula CONR^aR^b, a group having the formula COR^c, a group having the formula SO₂NR^aR^b, a group having the formula SO₂R^c or a group having the formula SOR^c, wherein R^a and R^b are the same or different and each is independently a hydrogen atom, a lower alkyl group which is unsubstituted or substituted with one or more groups selected from the group consisting of the Substituent group α

, a lower alkoxy group, a lower alkenyloxy group, a cycloalkyl group, an amino group, a mono-lower alkylamino group and a di-lower alkylamino group; and

R^c is a lower alkyl group

R⁶ is a hydrogen atom, a fluorine atom or a methoxy group;

R⁷ is 1 or 2 groups selected from the group consisting of a hydrogen atom, a hydroxyl group and a lower alkyl group,

or a pharmacologically acceptable salt thereof.

47. The compound according to claim 1, wherein A is a pyrrole group which is unsubstituted or substituted with two groups from the Substituent group δ

;

R¹ is a phenyl, 3-cyanophenyl, 4-fluorophenyl, 3-fluorophenyl, 4-chlorophenyl, 3-chlorophenyl, 2,4-difluorophenyl, 3,4-difluorophenyl, 3,4-dichlorophenyl, 3,4,5-trifluorophenyl, 3-chloro-4-fluorophenyl, 3-methoxyphenyl, 3-difluoromethoxyphenyl, 3-trifluoromethoxyphenyl, 3-trifluoromethylphenyl or 4-fluoro-3-methoxyphenyl group;

R² is a 4-pyridyl group or a 4-pyrimidinyl group, of which the 2-position is unsubstituted or substituted with one group selected from the group consisting of the Substituent group α and

the Substituent group β

;

m is 1;

R³ is a group having the formula (IIb); and

the Ring B is a pyrrolidine or pyrroline group;

Z is a phenylene group or a thiophenediyl group;

R⁵ is a carbamoyl, N-methylcarbamoyl, N-ethylcarbamoyl, N-propylcarbamoyl, N-isopropylcarbamoyl, N-cyclopropylcarbamoyl, N-cyclopentylcarbamoyl, N-(2-fluoroethyl)carbamoyl, N-(2-methoxyethyl)carbamoyl, N-methylsulfamoyl, N-ethylsulfamoyl, N-propylsulfamoyl, N-isopropylsulfamoyl, N-cyclopropylsulfamoyl, N-cyclopentylsulfamoyl, N-(2-fluoroethyl)sulfamoyl, N-(methoxyethyl)sulfamoyl, N-methoxysulfamoyl, methanesulfonyl, ethanesulfonyl, propanesulfonyl, methanesulfinyl, ethanesulfinyl or propanesulfinyl group;

R⁶ is a hydrogen atom, a fluorine atom or a methoxy group; and

R⁷ is 1 or 2 groups selected from the group consisting of a hydrogen atom, a hydroxyl group and a lower alkyl group,

or a pharmacologically acceptable salt thereof.

48. The compound according to claim 1, wherein A is a pyrrole group;

R¹ is a phenyl, 4-fluorophenyl, 3-fluorophenyl, 3-chlorophenyl, 3,4-difluorophenyl, 3-chloro-4-fluorophenyl or 3-trifluoromethylphenyl group;

R² is a 4-pyridyl group or a 4-pyrimidinyl group, of which the 2-position is unsubstituted or substituted with one group selected from the group consisting of a methoxy, amino, methylamino, benzylamino and α

-methylbenzylamino group;

m is 1;

R³ is a group having the formula (IIb); and

the Ring B is a pyrrolidine or pyrroline group;

Z is a phenylene group or a thiophenediyl group;

R⁵ is a carbamoyl, N-methylcarbamoyl, N-ethylcarbamoyl, N-propylcarbamoyl, N-isopropylcarbamoyl, N-cyclopropylcarbamoyl, N-cyclopentylcarbamoyl, N-(2-fluoroethyl)carbamoyl, N-(2-methoxyethyl)carbamoyl, N-methylsulfamoyl, N-ethylsulfamoyl, N-propylsulfamoyl, N-isopropylsulfamoyl, N-cyclopropylsulfamoyl, N-cyclopentylsulfamoyl, N-(2-fluoroethyl)sulfamoyl, N-(methoxyethyl)sulfamoyl, N-methoxysulfamoyl, methanesulfonyl, ethanesulfonyl, propanesulfonyl, methanesulfinyl, ethanesulfinyl or propanesulfinyl group;

R⁶ is a hydrogen atom;

R⁷ is a hydrogen atom,

R⁷ is a hydrogen atom,

or a pharmacologically acceptable salt thereof.

49. The compound according to any one of claims 44 to 48, wherein the compound having the formula (I) is a compound having one of the following formulae:

, wherein R⁴ and R^4′

are the same or different and each represents independently a hydrogen atom or a group from the Substituent group δ

, or a pharmacologically acceptable salt thereof.

50. The compound according to any one of claims 44 to 48, wherein the compound having the formula (I) is a compound having either one of the following formulae:

, wherein R⁴ and R^4′

are the same or different and each represents independently a hydrogen atom or a group selected from the Substituent group δ

, or a pharmacologically acceptable salt thereof.

51. A pharmaceutical composition comprising a pharmaceutically effective amount of the compound according to claim 1, or a pharmacologically acceptable salt thereof as an active ingredient and a pharmaceutically acceptable carrier.

52. A pharmaceutical composition comprising a pharmaceutically effective amount of the compound according to claim 36, or a pharmacologically acceptable salt thereof as an active ingredient and a pharmaceutically acceptable carrier.

53. A method of inhibiting production of inflammatory cytokines comprising administering a pharmaceutically effective amount of the compound of claim 1 or a pharmacologically acceptable salt thereof to a warm-blooded animal.

54. The method according to claim 53, wherein the warm-blooded animal is a human.

55. A method for prevention or treatment of a disease associated with inflammatory cytokines comprising administering a pharmaceutically effective amount of the compound of claim 1 or a pharmacologically acceptable salt thereof to a warm-blooded animal.

56. The method according to claim 55, wherein the warm-blooded animal is a human.

57. A method for treatment or relief of fever, pain and/or inflammation comprising administering a pharmaceutically effective amount of the compound of claim 1 or a pharmacologically acceptable salt thereof to a warm-blooded animal.

58. The method of claim 57, wherein the warm-blooded animal is a human.

59. A method for prevention or treatment of rheumatoid arthritis comprising administering a pharmaceutically effective amount of the compound of claim 1 or a pharmacologically acceptable salt thereof to a warm-blooded animal.

60. The method of claim 59, wherein the warm-blooded animal is a human.

61. A method for prevention or treatment of osteoarthritis comprising administering a pharmaceutically effective amount of the compound of claim 1 or a pharmacologically acceptable salt thereof to a warm-blooded animal.

62. The method according to claim 61, wherein the warm-blooded animal is a human.

63. A method for prevention or treatment of septicemic disease, psoriasis, Crohn'"'"'s disease, ulcerative colitis, diabetes mellitus, arterial sclerosis or hepatitis comprising administering a pharmaceutically effective amount of the compound of claim 1 or a pharmacologically acceptable salt thereof to a warm-blooded animal.

64. The method according to claim 63, wherein the warm-blooded animal is a human.

65. A method for prevention or treatment of osteoporosis, asthma, diffuse lupus erthematosus, nephritis, a tumor, ischemic heart disease, an allergic disease or Alzheimer'"'"'s disease comprising administering a pharmaceutically effective amount of the compound of claim 1 or a pharmacologically acceptable salt thereof to a human.

66. A method of inhibiting production of inflammatory cytokines comprising administering a pharmaceutically effective amount of the compound of claim 36 or a pharmacologically acceptable salt thereof to a warm-blooded animal.

67. The method according to claim 66, wherein the warm-blooded animal is a human.

68. A method for prevention or treatment of a disease associated with inflammatory cytokines comprising administering a pharmaceutically effective amount of the compound of claim 36 or a pharmacologically acceptable salt threof to a warm-blooded animal.

69. The method according to claim 68, wherein the warm-blooded animal is a human.

70. A method for treatment or relief of fever, pain and/or inflammation comprising administering a pharmaceutically effective amount of the compound of claim 36 or a pharmacologically acceptable salt thereof to a warm-blooded animal.

71. The method according to claim 70, wherein the warm-blooded animal is a human.

72. A method for prevention or treatment of rheumatoid arthritis comprising administering a pharmaceutically effective amount of the compound of claim 36 or a pharmacologically acceptable salt thereof to a warm-blooded animal.

73. The method according to claim 72, wherein the warm-blooded animal is a human.

74. A method for prevention or treatment of osteoarthritis comprising administering a pharmaceutically effective amount of the compound of claim 36 or a pharmacologically acceptable salt thereof to a warm-blooded animal.

75. The method according to claim 74, wherein the warm-blooded animal is a human.

76. A method for prevention or treatment of septicemic disease, psoriasis, Crohn'"'"'s disease, ulcerative colitis, diabetes mellitus or hepatitis comprising administering a pharmaceutically effective amount of the compound of claim 36 or a pharmacologically acceptable salt thereof to a warm-blooded animal.

77. The method according to claim 76, wherein the warm-blooded animal is a human.

78. A method for treatment of osteoporosis, asthma, diffuse lupus erthmatosus, nephritis, a tumor, ischemic heart disease, an allergic disease or Alzheimer'"'"'s disease comprising administering a pharmaceutically effective amount of the compound of claim 36, or a pharmacologically acceptable salt thereof to a human.

79. The compound according to claim 1, wherein the compound is 2-(4-fluorophenyl)-4-[1-[4-(N-methylsulfamoyl)phenethyl]-1,2,3,6-tetrahydropyridin-4-yl]-3-(pyridin-4-yl)-1H-pyrrole, or a pharmacologically acceptable salt thereof.

80. The compound according to claim 1, wherein the compound is 4-[1-[4-(N-ethylcarbamoyl)phenethyl]-1,2,3,6-tetrahydropyridin-4-yl]-2-(4-fluorophenyl)-3-(pyridin-4-yl)-1H-pyrrole, or a pharmacologically acceptable salt thereof.

81. The compound according to claim 1, wherein the compound is 2-(4-fluorophenyl)-4-[1-[4-(N-propylsulfamoyl)phenethyl]-1,2,3,6-tetrahydropyridin-4-yl]-3-(pyridin-4-yl)-1H-pyrrole, or a pharmacologically acceptable salt thereof.

82. The compound according to claim 1, wherein the compound is 2-(3-chloro-4-fluorophenyl)-4-[1-[4-(N-methylsulfamoyl)phenethyl]-1,2,3,6-tetrahydropyridin-4-yl]-3-(pyridin-4-yl)-1H-pyrrole, or a pharmacologically acceptable salt thereof.

83. The compound according to claim 1, wherein the compound is 4-[1-[4-[N-(2-fluoroethyl)sulfamoyl]phenethyl]-1,2,3,6-tetrahydropyridin-4-yl]-2-(4-fluorophenyl)-3-(pyridin-4-yl)-1H-pyrrole, or a pharmacologically acceptable salt thereof.

84. The compound according to claim 1, wherein the compound is 4-[1-[4-[N-dimethylsulfamoyl)phenethyl]-1,2,3,6-tetrahydropyridin-4-yl]-2-(4-fluorophenyl)-3-(pyridin-4-yl)-1H-pyrrole, or a pharmacologically acceptable salt thereof.

85. The compound according to claim 1, wherein the compound is 2-(4-fluorophenyl)-4-[1-[4-[N-(2-methoxyethyl)sulfamoyl]phenethyl]-1,2,3,6-tetrahydropyridin-4-yl]-3-(pyridin-4-yl)-1H-pyrrole, or a pharmacologically acceptable salt thereof.

86. The compound according to claim 1, wherein the compound is 2-(4-fluorophenyl)-4-[1-(4-(N-methanesulfonyl)phenethyl]-1,2,3,6-tetrahydropyridin-4-yl]-3-(pyridin-4-yl)-1H-pyrrole, or a pharmacologically acceptable salt thereof.

87. The compound according to claim 1, wherein the compound is 2-(3-chloro-4-fluorophenyl)-4-[1-(4-methanesulfonyl)phenethyl]-1,2,3,6-tetrahydropyridin-4-yl]-3-(pyridin-4-yl)-1H-pyrrole, or a pharmacologically acceptable salt thereof.

88. The compound according to claim 1, wherein the compound is 2-(4-fluorophenyl)-4-[1-(4-methanesulfinylphenethyl)-1,2,3,6-tetrahydropyridin-4-yl]-3-(pyridin-4-yl)-1H-pyrrole, or a pharmacologically acceptable salt thereof.

89. The compound according to claim 1, wherein the compound is 2-(3-chloro-4-fluorophenyl)-4-[1-(4-methanesulfinylphenethyl)-1,2,3,6-tetrahydropyridin-4-yl]-3-(pyridin-4-yl)-1H-pyrrole, or a pharmacologically acceptable salt thereof.

90. The compound according to claim 1, wherein the compound is 2-(4-fluorophenyl)-4-[1-[4-(2-methoxyethyl)-sulfonylphenethyl]-1,2,3,6-tetrahydropyridin-4-yl]-3-(pyridin-4-yl)-1H-pyrrole, or a pharmacologically acceptable salt thereof.

91. The compound according to claim 1, wherein the compound is 2-(4-fluorophenyl)-4-[1-[4-(2-hydroxyethyl)sulfonylphenethyl]-1,2,3,5,6-tetrahydropyridin-4-yl]-3-(pyridin-4-yl)-1H-pyrrole, or a pharmacologically acceptable salt thereof.

92. The compound according to claim 1, wherein the compound is 2-(3-chloro-4-fluorophenyl)-4-[1-[4-(2-methoxyethyl)sulfonylphenethyl]-1,2,3,6-tetrahydropyridin-4-yl]-3-(pyridin-4-yl)-1H-pyrrole, or a pharmacologically acceptable salt thereof.

93. The compound according to claim 1, wherein the compound is 2-(3-chloro-4-fluorophenyl)-4-[1-[4-(2-hydroxyethyl)sulfonylphenethyl]-1,2,3,6-tetrahydropyridin-4-yl]-3-(pyridin-4-yl)-1H-pyrrole, or a pharmacologically acceptable salt thereof.

94. The compound according to claim 1, wherein the compound is 4-[1-(4-methanesulfonylphenethyl]-1,2,3,6-tetrahydropyridin-4-yl]-2-(3-methylphenyl)-3-(pyridin-4-yl)-1H-pyrrole, or a pharmacologically acceptable salt thereof.

95. The compound according to claim 1, wherein the compound is 4-[1-(4-(2-hydroxyethyl)sulfonylphenethyl]-1,2,3,6-tetrahydropyridin-4-yl]-2-(3-methylphenyl)-3-(pyridin-4-yl)-1H-pyrrole, or a pharmacologically acceptable salt thereof.

96. The compound according to claim 1, wherein the compound is 4-[1-[4-(2-methoxyethyl)sulfonylphenethyl]-1,2,3,6-tetrahydropyridin-4-yl)-2-(3-methylphenyl)-3-(pyridin-4-yl)-1H-pyrrole, or a pharmacologically acceptable salt thereof.