Patent ID: 6423716
Filing Date: 2002-07-23
Classification: C07D

Abstract:
A nitrogen-containing heterocyclic compound represented by formula (I): wherein W represents 1,4-piperazinediyl or 1,4-homopiperazinediyl in which carbon atoms on the ring may be substituted with 1 to 4 alkyl groups which are the same or different; U represents NR1R2 (wherein R1 represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic alkyl group (said alicyclic alkyl group is selected from the group consisting of monocyclic groups having from 3 to 12 carbon atoms, pinanyl, 1,7,7-trimethylbicyclo[2.2.1]heptyl, adamantyl, hexahydro-4,7-methano-1H-indenyl and 4-hexylbicyclo[2.2.2]octyl), an optionally substituted alicyclic heterocyclic group selected from the group consisting of tetrahydrofuryl, tetrahydropyranyl, pyrrolidinyl, piperidyl, piperazinyl, morpholinyl and thiomorpholinyl, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted heteroarylalkyl group; and R2 represents a hydrogen atom, a substituted alkyl group, a substituted or unsubstituted alicyclic alkyl group (said alicyclic alkyl group is selected from the group consisting of monocyclic groups having from 3 to 12 carbon atoms, pinanyl, 1,7,7-trimethylbicyclo[2.2.1]heptyl, adamantyl, hexahydro-4,7-methano-1H-indenyl and 4-hexylbicyclo[2.2.2]octyl), an optionally substituted alicyclic heterocyclic group selected from the group consisting of tetrahydrofuryl, tetrahydropyranyl, pyrrolidinyl, piperidyl, piperazinyl, morpholinyl and thiomorpholinyl, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroarylalkyl group, CQR1A (wherein Q represents an oxygen atom or a sulfur atom; and R1A has the same meaning as R1), or SO2R3 (wherein R3 represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic alkyl group (said alicyclic alkyl group is selected from the group consisting of monocyclic groups having from 3 to 12 carbon atoms, pinanyl, 1,7,7-trimethylbicyclo[2.2.1]heptyl, adamantyl, hexahydro-4.7-methano-1H-indenyl and 4-hexylbicyclo[2.2.2]octyl), an optionally substituted alicyclic heterocyclic group selected from the group consisting of tetrahydrofuryl, tetrahydropyranyl, pyrrolidinyl, piperidyl, piperazinyl, morpholinyl and thiomorpholinyl, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted heteroarylalkyl group)), OR4 (wherein R4 has the same meaning as R3), or SR5 (wherein R5 has the same meaning as R3); V represents an oxygen atom, a sulfur atom, Nâ€”R6 (wherein R6 has the same meaning as R1 or represents a cyano group, a hydroxyl group, a nitro group, a carbamoyl group, COOR3A (wherein R3A has the same meaning as R3), CQAR1B (wherein QA has the same meaning as Q, and R1B has the same meaning as R1), or SO2R3B (wherein R3B has the same meaning as R3)), or CR7R8 (wherein R7 and R8 are the same or different and each represents a hydrogen atom, a cyano group, a nitro group, COOR3C (wherein R3C has the same meaning as R3), or SO2R3D (wherein R3D has the same meaning as R3)), with the proviso that, when R1 is hydrogen, R6 and R2 may be exchanged, V may represent Nâ€”R2, or â€”R6, and when U is OR4 or SR5, V represents Nâ€”R6 or CR7R8, at least one of X, Y and Z represents a nitrogen atom, and the others are the same or different, and each represents a nitrogen atom or Câ€”RA A has the same meaning as R1, or represents a halogen atom, a cyano group, a nitro group, NR9R10 {wherein R9 and R10 are the same or different, and each has the same meaning as R1, or represents SO2R3E (wherein R3E has the same meaning as R3) or CQBR11 (wherein QB has the same meaning as Q; and R11 has the same meaning as R1, or represents OR3F (wherein R3F has the same meaning as R3) or NR1CR1D (wherein R1C and R1D are the same or different, and each has the same meaning as R1, or R1C and R1D are combined to represent a substituted or unsubstituted nitrogen-containing heterocyclic group)), or R9 and R10 are combined to represent a substituted or unsubstituted nitrogen-containing heterocyclic group}, CQCR11A (wherein QC has the same meaning as Q; and R11A has the same meaning as R11), OR12 {wherein R12 has the same meaning as R1, or represents CQDR13 (wherein QD has the same meaning as Q; and R13 has the same meaning as R1, or represents OR3G (wherein R3G has the same meaning as R3), SR3H (wherein R3H has the same meaning as R3), or NR1ER1F (wherein R1E and R1F are the same or different, and each has the same meaning as R1, or R1E and R1F are combined to represent a substituted or unsubstituted nitrogen-containing heterocyclic group)), or SO2R3I (wherein R3I has the same meaning as R3)}, SR1G (wherein R1G has the same meaning as R1), SOR3J (wherein R3J has the same meaning as R3) or SO2R14 (wherein R14 has the same meaning as R3, or represents OR1H (wherein R1H has the same meaning as R1) or NR1IR1J (wherein R1I and R1J are the same or different, and each has the same meaning as R1, or R1I and R1J are combined to represent a substituted or unsubstituted nitrogen-containing heterocyclic group)) >, and (1) when V represents Nâ€”R6 or CR7R8, and U represents NR1R2, OR4, or SR5, D1, D2, D3 and D4 each independently represent Câ€”RB (wherein RB has the same meaning as RA), a nitrogen atom, an oxygen atom, or a sulfur atom; or optional adjoining two among D1 to D4 may be combined to represent a nitrogen atom, Nâ€”R2A (wherein R2A has the same meaning as R2, or represents an alkyl group or CQENHR3K (wherein QE has the same meaning as Q; and R3K has the same meaning as R3)), an oxygen atom, or a sulfur atom, and the remains among D1 to D4 may represent Câ€”RBâ€² (wherein RBâ€² has the same meaning as RA), Nâ€”R2A (wherein R2A has the same meaning as R2A, or a nitrogen atom; and in these two cases, the optional adjoining two selected from D1 to D4 may represent Câ€”RBâ€³ (wherein two RBâ€³s, together with the two adjoining carbon atoms, represent an optionally substituted alicyclic alkene selected from the group consisting of cyclobutene, cyclopentene, cyclohexene, cycloheptene, cyclooctene and cyclododecene, substituted or unsubstituted pyrrole, substituted or unsubstituted pyrazole, substituted or unsubstituted imidazole, substituted or unsubstituted imidazol-2-one, substituted or unsubstituted imidazole-2-thione, substituted or unsubstituted triazole, substituted or unsubstituted furan, substituted or unsubstituted 1,3-dioxole, substituted or unsubstituted 1,4-dioxene, substituted or unsubstituted thiophene, substituted or unsubstituted oxazole, substituted or unsubstituted oxadiazole, substituted or unsubstituted isoxazole, substituted or unsubstituted thiazole, substituted or unsubstituted isothiazole, substituted or unsubstituted thiadiazole, substituted or unsubstituted pyridine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyrimidine, substituted or unsubstituted pyridazine, substituted or unsubstituted triazine, substituted or unsubstituted tetrazine, or substituted or unsubstituted benzene), and (2) when V represents an oxygen atom or a sulfur atom, and U represents NR1R2 (2-1) at least one of D1 to D4 represents a nitrogen atom, an oxygen atom or a sulfur atom; optional adjoining two among D1 to D4 are combined to represent a nitrogen atom, Nâ€”R2B (wherein R2B has the same meaning as R2), or an oxygen atom; or D2 and D3 are combined to represent a sulfur atom; and in these three cases, the remains among D1 to D4 represent a nitrogen atom, Nâ€”R2Bâ€² (wherein R2Bâ€² has the same meaning as R2), an oxygen atom, a sulfur atom, or Câ€”RC (wherein the RCs each independently have the same meaning as RA, or optional two RCsâ€² adjoining adjacent carbon atoms, together with the two adjoining carbon atoms, may represent an optionally substituted alicyclic alkene selected from the group consisting of cyclobutene, cyclopentene, cyclohexene, cycloheptene, cyclooctene and cyclododecene, substituted or unsubstituted pyrrole, substituted or unsubstituted pyrazole, substituted or unsubstituted imidazole, substituted or unsubstituted imidazol-2-one, substituted or unsubstituted imidazole-2-thione, substituted or unsubstituted triazole, substituted or unsubstituted furan, substituted or unsubstituted 1,3-dioxole, substituted or unsubstituted 1,4-dioxene, substituted or unsubstituted oxazole, substituted or unsubstituted oxadiazole, substituted or unsubstituted isoxazole, substituted or unsubstituted thiophene, substituted or unsubstituted thiazole, substituted or unsubstituted isothiazole, substituted or unsubstituted thiadiazole, substituted or unsubstituted pyridine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyrimidine, substituted or unsubstituted pyridazine, substituted or unsubstituted triazine, substituted or unsubstituted tetrazine, or substituted or unsubstituted benzene), (2-2) D1 and D2 are combined to represent a sulfur atom; D3 represents Câ€”RCâ€² (wherein RCâ€² has the same meaning as RA); and D4 represents a nitrogen atom, or D3 and D4 represent Câ€”RCâ€³ (wherein RCâ€³s, together with two adjoining carbon atoms, represent an optionally substituted alicyclic alkene selected from the group consisting of cyclobutene, cyclopentene, cyclohexene, cycloheptene, cyclooctene and cyclododecene, substituted or unsubstituted pyrrole, substituted or unsubstituted pyrazole, substituted or unsubstituted imidazole, substituted or unsubstituted imidazol-2-one, substituted or unsubstituted imidazole-2-thione, substituted or unsubstituted triazole, substituted or unsubstituted furan, substituted or unsubstituted 1,3-dioxole, substituted or unsubstituted 1,4-dioxene, substituted or unsubstituted oxazole, substituted or unsubstituted oxadiazole, substituted or unsubstituted isoxazole, substituted or unsubstituted thiophene, substituted or unsubstituted thiazole, substituted or unsubstituted isothiazole, substituted or unsubstituted thiadiazole, substituted or unsubstituted pyridine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyrimidine, substituted or unsubstituted pyridazine, substituted or unsubstituted triazine, substituted or unsubstituted tetrazine, or substituted or unsubstituted benzene), (2-3) D3 and D4 are combined to represent a sulfur atom; D2 represents Câ€”RCâ€³ (wherein RCâ€²â€³ has the same meaning as RA); and D1 represents a nitrogen atom, or D1 and D2 represent Câ€”RCâ€³â€³ (wherein RCâ€³â€³ has the same meaning as RCâ€³), or (2-4) D1, D2, D3 and D4 represent Câ€”RD (wherein in RDs, optional two RDsâ€² adjoining adjacent carbon atoms, together with the two adjoining carbon atoms, represent an optionally substituted alicyclic alkene selected from the group consisting of cyclobutene, cyclopentene, cyclohexene, cycloheptene, cyclooctene and cyclododecene, substituted or unsubstituted pyrrole, substituted or unsubstituted pyrazole, substituted or unsubstituted furan, substituted or unsubstituted thiophene, substituted or unsubstituted oxadiazole, substituted or unsubstituted isoxazole, substituted or unsubstituted isothiazole, substituted or unsubstituted thiadiazole, substituted or unsubstituted pyridine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyrimidine, substituted or unsubstituted pyridazine, substituted or unsubstituted triazine, or substituted or unsubstituted tetrazine, and each of the remaining RDs independently represents the same meaning as RA), or a pharmaceutically acceptable salt thereof.