Nitrogenous fused heteroaromatic ring derivative

A compound of the formula (I):

• wherein:
• A1 represents a hydrogen atom, a group selected from a substituent group β optionally having 1 or 2 groups selected from a substituent group α, or a phenyl or heteroaryl group, which optionally have 1 or 2 groups selected from a substituent group γ;
• j and k each independently indicate 0 or 1;
• when j is 0, then a formula (III-1):
• in the formula (I) represents a double bond, and when j is 1, then the formula (II-1) represents a group of:
• (wherein A2 has the same meaning as A1);
• when k is 0, then a formula (III-2):
• in the formula (I) represents a double bond, and when k is 1, then the formula (III-2) represents a group of:
• (wherein A3 has the same meaning as A1);
• regarding W1 and W2, one of W1 and W2 is A4 and the other is E-O—W, or when j is 1, then W1 may be E-O—W and A2-C═C—W2 may together form a benzene ring or a heteroaryl ring having from 1 to 3, the same or different hetero atoms selected from a group consisting of a nitrogen atom, a sulfur atom and an oxygen atom (the benzene ring and the heteroaryl ring may be substituted with a nitro group, a hydroxy group, a lower alkyl group, a halo-lower alkyl group, a halogen atom, a lower alkoxy group, an alkanoylamino group);
• E represents a phenyl group optionally having from 1 to 3 groups selected from a substituent group δ, or a 5- or 6-membered monocyclic aromatic heterocyclic group having 1 or more, preferably from 1 to 3, the same or different hetero atoms selected from a group consisting of a nitrogen atom, an oxygen atom and a sulfur atom, or represents a condensed-cyclic aromatic heterocyclic group that the monocyclic aromatic heterocyclic group forms together with an aryl group;
• W represents a formula (II-1):
• a formula (II-2):
• or a formula (II-3):
• wherein G1 and G2 may be the same or different, each representing a lower alkyl group (the lower alkyl group may be further substituted with a halogen atom) or a cycloalkyl group, or G1 and G2 form, together with the nitrogen atom adjacent to G1 and G2, a 5- to 8-membered aliphatic hetero-ring (the hetero-ring may have, in the ring, 1 or 2 groups of a lower alkyl group optionally substituted with a halogen atom or a halogen atom) or a bicyclo-ring;
• m1 indicates an integer of from 2 to 4;
• m2 and m3 each indicate an integer of from 1 to 3;
• (CH2)m1 in the formula (II-1) may be further substituted with a lower alkyl group having from 1 to 3 carbon atoms;
• wherein substituent group α is selected from:
• an amino group, a nitro group, a cyano group, a hydroxy group, a halogen atom, a lower alkylsulfonyl group, a lower alkyl group (the lower alkyl group may be substituted with a halogen atom), a lower cycloalkyl group (the lower cycloalkyl group may be substituted with a halogen atom), a lower alkoxy group (the lower alkoxy group may be substituted with a halogen atom), a lower cycloalkoxy group (the lower cycloalkoxy group may be substituted with a halogen atom), an aryloxy group, an alaryloxy group, an aryl group, a heteroaryl group, a mono-lower alkylcarbamoyl group, a di-lower alkylcarbamoyl group, a lower alkylcarboxamido group, an arylcarboxamido group, a heteroarylcarboxamido group, an alkanoyl group, and an alkylthio group;
• wherein substituent group β is selected from:
• an amino group, a lower alkylsulfonyl group, a lower alkyl group, a lower cycloalkyl group, a lower alkoxy group, a lower cycloalkoxy group, the lower alkyl group being optionally substituted with a halogen atom, a lower cycloalkyl group (the cycloalkyl group may be substituted with a halogen atom), a lower alkoxy group (the lower alkoxy group may be substituted with a halogen atom), a lower cycloalkoxy group (the lower cycloalkoxy group may be substituted with a halogen atom), a carbamoyl group, and a mono- or di-lower alkylcarbamoyl group;
• wherein substituent group γ is selected from:
• an amino group, a nitro group, a cyano group, a hydroxy group, a lower alkylsulfonyl group, a halogen atom, a lower alkyl group (the lower alkyl group may be substituted with a halogen atom), a lower cycloalkyl group (the lower alkyl group may be substituted with a halogen atom), a lower alkoxy group (the lower alkoxy group may be substituted with a halogen atom or a hydroxy group), a lower cycloalkoxy group (the lower alkyl group may be substituted with a halogen atom), an aryloxy group, an alaryloxy group, an aryl group, a heteroaryl group, a mono-lower alkylcarbamoyl group, a di-lower alkylcarbamoyl group, a lower alkylcarboxamido group, an arylcarboxamido group, a heteroarylcarboxamido group, an alkanoyl group, an alkylthio group, an alkoxycarbonylamino group, an alkylsulfonylamino group, an arylsulfonylamino group, and an alkylaminosulfonyl group or an arylaminosulfonyl group;
• wherein substituent group δ is selected from:
• a halogen atom, a nitro group, a lower alkyl group, a halo-lower alkyl group, a hydroxy group, a hydroxy-lower alkyl group, a cyclo-lower alkyl group, a lower alkenyl group, a hydroxyl group, a lower alkoxy group, a halo-lower alkoxy group, a lower alkylamino group, a di-lower alkylamino group, a lower alkylthio group, a carboxyl group, a lower alkanoyl group, and a lower alkoxycarbonyl group;
• or a pharmaceutically-acceptable salt thereof.

A compound which is selected from the group consisting of:

• 2-[4-(3-piperidin-1-ylpropoxy)-phenyl]-3aH-pyrazolo[1,5-d][1,2,4]triazine,
• 2-[4-(1-cyclopentyl-piperidin-4-yloxy)phenyl]-3aH-pyrazolo[1,5-d][1,2,4]triazine,
• 3-methyl-2-[4-(3-piperidin-1-ylpropoxy)-phenyl]-3aH-pyrazolo[1,5-d][1,2,4]triazine,
• 3-ethyl-2-[4-(3-piperidin-1-ylpropoxy)phenyl]-3aH-pyrazolo[1,5-d][1,2,4]triazine,
• 7-methyl-2-[4-(3-piperidin-1-ylpropoxy)-phenyl]-3aH-pyrazolo[1,5-d][1,2,4]triazine,
• 7-(5-methyl-isoxazol-3-yl)-2-[4-(3-piperidin-1-ylpropoxy)-phenyl]-3aH-pyrazolo[1,5-d][1,2,4]triazine,
• 7-phenyl-2-[4-(3-piperidin-1-ylpropoxy)-phenyl]-3aH-pyrazolo[1,5-d][1,2,4]triazine,
• 3-methyl-7-phenyl-2-[4-(3-piperidin-1-ylpropoxy)-phenyl]-3aH-pyrazolo[1,5-d][1,2,4]triazine,
• 3-methyl-2-[4-(3-piperidin-1-ylpropoxy)-phenyl]-7-(pyridin-3-yl)-3aH-pyrazolo[1,5-d][1,2,4]triazine,
• 6-[4-(3-piperidin-1-ylpropoxy)-phenyl]-[1,2,4]triazolo[4,3-b]pyridazine,
• 7-methyl-6-[4-(3-piperidin-1-ylpropoxy)-phenyl]-[1,2,4]triazolo[4,3-b]pyridazine,
• 3-methyl-6-[4-(3-piperidin-1-ylpropoxy)-phenyl]-[1,2,4]triazolo[4,3-b]pyridazine,
• 6-[4-(3-piperidin-1-ylpropoxy)-phenyl]-3-trifluoromethyl-[1,2,4]triazolo[4,3-b]pyridazine,
• 3-tert-butyl-6-[4-(3-piperidin-1-ylpropoxy)-phenyl]-[1,2,4]triazolo[4,3-b]pyridazine,
• 3-phenyl-6-[4-(3-piperidin-1-ylpropoxy)-phenyl]-[1,2,4]triazolo[4,3-b]pyridazine,
• 6-[4-(3-piperidin-1-ylpropoxy)-phenyl]-3-(pyridin-2-yl)-[1,2,4]triazolo[4,3-b]pyridazine,
• 6-[4-(3-piperidin-1-ylpropoxy)-phenyl]-3-(pyridin-3-yl)-[1,2,4]triazolo[4,3-b]pyridazine,
• 7-methyl-3-phenyl-6-[4-(3-piperidin-1-ylpropoxy)-phenyl]-[1,2,4]triazolo[4,3-b]pyridazine,
• 6-methyl-7-[4-(3-piperidin-1-ylpropoxy)-phenyl]-[1,2,4]triazolo[4,3-b]pyridazine,
• 3,6-dimethyl-7-[4-(3-piperidin-1-ylpropoxy)-phenyl]-[1,2,4]triazolo[4,3-b]pyridazine,
• 6-methyl-3-phenyl-[4-(3-piperidin-1-ylpropoxy)-phenyl]-[1,2,4]triazolo[4,3-b]pyridazine,
• 6-[4-(3-piperidin-1-ylpropoxy)-phenyl]-pyrido[3,2-d][1,2,4]triazolo[4,3-b]pyridazine,
• 4-(pyrido[3,2-d][1,2,4]triazolo[4,3-b]pyridazin-6-yl)-phenol,
• 4-(pyrido[2,3-d][1,2,4]triazolo[4,3-b]pyridazin-6-yl)-phenol,
• 3-phenyl-6-[4-(3-piperidin-1-ylpropoxy)-phenyl]-pyrido[2,3-d][1,2,4]triazolo[4,3-b]pyridazine,
• 3-phenyl-6-[6-(3-piperidin-1-ylpropoxy)-pyridin-3-ylmethoxy]-[1,2,4]triazolo[3,4-a]phthalazine,
• 3-phenyl-6-[4-(3-piperidin-1-ylpropoxy)-phenyl]-[1,2,4]triazolo[3,4-a]phthalazine,
• 6-[4-(3-piperidin-1-ylpropoxy)-phenyl]-3-(pyridin-3-yl)-[1,2,4]triazolo[3,4-a]phthalazine,
• 6-[4-(3-piperidin-1-ylpropoxy)-phenyl]-3-(pyridin-2-yl)-[1,2,4]triazolo[3,4-a]phthalazine,
• 3-phenyl-6-[4-(3-piperidin-1-ylpropoxy)-phenyl]-pyrido[3,2-d][1,2,4]triazolo[4,3-b]pyridazine,
• 6-[4-(3-piperidin-1-ylpropoxy)-phenyl]-pyrido[2,3-d][1,2,4]triazolo[4,3-b]pyridazine,
• 3-methyl-6-[4-(3-piperidin-1-ylpropoxy)-phenyl]-pyrido[3,2-d][1,2,4]triazolo[4,3-b]pyridazine,
• 3-methyl-6-[4-(3-piperidin-1-ylpropoxy)-phenyl]-pyrido[2,3-d][1,2,4]triazolo[4,3-b]pyridazine,
• 6-[4-(3-piperidin-1-ylpropoxy)-phenyl]-[1,2,4]triazolo[3,4-a]phthalazine,
• 3-methyl-6-[4-(3-piperidin-1-ylpropoxy)-phenyl]-[1,2,4]triazolo[3,4-a]phthalazine,
• 6-[4-(3-piperidin-1-ylpropoxy)-phenyl]-3-trifluoromethyl-[1,2,4]triazolo[3,4-a]phthalazine,
• 3-tert-butyl-6-[4-(3-piperidin-1-ylpropoxy)-phenyl]-[1,2,4]triazolo[3,4-a]phthalazine,
• 6-[4-(1-cyclopentyl-piperidin-4-yloxy)-phenyl]-[1,2,4]triazolo[4,3-b]pyridazine,
• 6-[4-(1-cyclobutyl-piperidin-4-yloxy)-phenyl]-[1,2,4]triazolo[4,3-b]pyridazine,
• 6-[4-(1-cyclopentyl-piperidin-4-yloxy)-phenyl]-3-methyl-[1,2,4]triazolo[4,3-b]pyridazine,
• 6-[4-(1-cyclopentyl-piperidin-4-yloxy)-phenyl]-7-methyl-[1,2,4]triazolo[4,3-b]pyridazine,
• 7-[4-(3-piperidin-1-ylpropoxy)-phenyl]-[1,2,4]triazolo[4,3-b]pyridazine,
• 7-[4-(1-cyclopentyl-piperidin-4-yloxy)-phenyl]-3-methyl-[1,2,4]triazolo[4,3-b]pyridazine,
• 7-[4-(1-cyclopentyl-piperidin-4-yloxy)-phenyl]-6-methyl-[1,2,4]triazolo[4,3-b]pyridazine,
• 7-[4-(1-cyclopentyl-piperidin-4-yloxy)-phenyl]-3,6-dimethyl-[1,2,4]triazolo[4,3-b]pyridazine,
• 7-[4-(1-cyclopentyl-piperidin-4-yloxy)-phenyl]-[1,2,4]triazolo[4,3-b]pyridazine,
• 7-[4-(1-cyclobutyl-piperidin-4-yloxy)-phenyl]-[1,2,4]triazolo[4,3-b]pyridazine,
• 6-[4-(1-cyclopentyl-piperidin-4-yloxy)-phenyl]-[1,2,4]triazolo[3,4-a]phthalazine,
• 6-[4-(1-cyclopentyl-piperidin-4-yloxy)-phenyl]-3-methyl-[1,2,4]triazolo[3,4-a]phthalazine,
• 6-[4-(3-pyrrolidin-1-ylpropoxy)-phenyl]-[1,2,4]triazolo[4,3-b]pyridazine,
• 3-methyl-7-[4-(3-piperidin-1-ylpropoxy)-phenyl]-[1,2,4]triazolo[4,3-b]pyridazine,
• 7-[4-(1-cyclobutyl-piperidin-4-yloxy)-phenyl]-3-methyl-[1,2,4]triazolo[4,3-b]pyridazine,
• 6-[4-(1-cyclobutyl-piperidin-4-yloxy)-phenyl]-3-methyl-[1,2,4]triazolo[4,3-b]pyridazine,
• 6-[4-(1-cyclobutyl-piperidin-4-yloxy)-phenyl]-[1,2,4]triazolo[3,4-a]phthalazine,
• 6-[4-(1-cyclobutyl-piperidin-4-yloxy)-phenyl]-7-methyl-[1,2,4]triazolo[4,3-b]pyridazine,
• 7-[4-(1-cyclobutyl-piperidin-4-yloxy)-phenyl]-6-methyl-[1,2,4]triazolo[4,3-b]pyridazine,
• 7-[4-(1-cyclobutyl-piperidin-4-yloxy)-phenyl]-3,6-dimethyl-[1,2,4]triazolo[4,3-b]pyridazine,
• 6-[4-(1-cyclobutyl-piperidin-4-yloxy)-phenyl]-3-methyl-[1,2,4]triazolo[3,4-a]phthalazine,
• 6-{4-[3-(2,6-dimethylpiperizin-1-yl)propoxy]-phenyl}-[1,2,4]triazolo[4,3-b]pyridazine,
• 6-{4-[3-(2,5-dimethylpyrrolidin-1-yl)propoxy]-phe,
• N-methyl-6-[4-(3-piperidin-1-ylpropoxy)phenyl]-[1,2,4]triazolo[4,3-b]pyridazine-3-carboxamide,
• 3-(piperidin-1-ylcarbonyl)-6-[4-(3-piperidin-1-ylpropoxy)phenyl]-[1,2,4]triazolo[4,3-b]pyridazine,
• 6-[4-(3-methylpiperidin-1-ylpropoxy)-phenyl]-[1,2,4]triazolo[4,3-b]pyridazine,
• 6-[4-{3-[(3S)-3-fluoropyrrolidin-1-yl]propoxy}-phenyl)-[1,2,4]triazolo[4,3-b]pyridazine,
• 6-{4-[3-(3-methylpiperidin-1-yl)propoxy]-phenyl}-[1,2,4]triazolo[4,3-b]pyridazine,
• 6-{4-[3-(4-fluoropiperidin-1-yl)propoxy]-phenyl}-[1,2,4]triazolo[4,3-b]pyridazine,
• 6-{4-[3-(3-fluoropiperidin-1-yl)propoxy]-phenyl}-[1,2,4]triazolo[4,3-b]pyridazine,
• 6-[4-{3-[(2R)-(2-methylpyrrolidin-1-yl]propoxy)-phenyl}-[1,2,4]triazolo[4,3-b]pyridazine,
• 6-[4-{3-[(2S)-(2-methylpyrrolidin-1-yl]propoxy)-phenyl}-[1,2,4]triazolo[4,3-b]pyridazine,
• N,N-dimethyl-6-[4-{3-[(2R)-2-methylpyrrolidin-1-yl]propoxy)-phenyl}-[1,2,4]triazolo[3,4-a]phthalazine-3-carboxamide,
• 6-[4-(3-piperidin-1-ylpropoxy)-phenyl]-pyrido[3,4-d][1,2,4]triazolo[4,3-b]pyridazine,
• 6-[4-(3-pyrrolidin-1-ylpropoxy)-phenyl]-pyrido[3,4-d][1,2,4]triazolo[4,3-b]pyridazine,
• 6-[4-{3-[(3S)-3-methylpiperidin-1-yl]propoxy}-phenyl]-pyrido[3,4-d][1,2,4]triazolo[4,3-b]pyridazine,
• 3-methyl-6-[4-(3-piperidin-1-ylpropoxy)-phenyl]-pyrido[3,4-d][1,2,4]triazolo[4,3-b]pyridazine,
• 3-methyl-6-[4-(3-pyrrolidin-1-ylpropoxy)-phenyl]-pyrido[3,4-d][1,2,4]triazolo[4,3-b]pyridazine,
• 3-methyl-6-[4-{3-[(3S)-3-methylpiperidin-1-yl]propoxy}-phenyl]-pyrido[3,4-d][1,2,4]triazolo[4,3-b]pyridazine,
• 6-[4-{3-[(2R)-2-methylpyrrolidin-1-yl]propoxy}-phenyl]-pyrido[3,4-d][1,2,4]triazolo[4,3-b]pyridazine,
• 3-methyl-6-[4-{3-[(2R)-2-methylpyrrolidin-1-yl]propoxy}-phenyl]-pyrido[3,4-d][1,2,4]triazolo[4,3-b]pyridazine,
• 6-[4-(1-isopropylpiperidin-4-yloxy)phenyl]pyrido[3,4-d][1,2,4]triazolo[4,3-b]pyridazine,
• 6-[4-(1-cyclobutylpiperidin-4-yloxy)phenyl]pyrido[3,4-d][1,2,4]triazolo[4,3-b]pyridazine,
• 6-[4-(1-cyclopentylpiperidin-4-yloxy)phenyl]pyrido[3,4-d][1,2,4]triazolo[4,3-b]pyridazine,
• 6-[4-(1-isopropylpiperidin-4-yloxy)phenyl]-3-methylpyrido[3,4-d][1,2,4]triazolo[4,3-b]pyridazine,
• 6-[4-(1-cyclobutylpiperidin-4-yloxy)phenyl]-3-methylpyrido[3,4-d][1,2,4]triazolo[4,3-b]pyridazine,
• 6-[4-(1-cyclopentylpiperidin-4-yloxy)phenyl]-3-methylpyrido[3,4-d][1,2,4]triazolo[4,3-b)pyridazine,
• 3-methyl-6-[4-(3-pyrrolidin-1-ylpropoxy)-phenyl]-pyrido[3,2-d][1,2,4]triazolo[4,3-b]pyridazine,
• 3-methyl-6-[4-(3-pyrrolidin-1-ylpropoxy)-phenyl]-pyrido[2,3-d][1,2,4]triazolo[4,3-b]pyridazine,
• 3-methyl-6-(4-{3-[(3S)-3-methylpiperidin-1-yl]propoxy}-phenyl]-pyrido[3,2-d][1,2,4]triazolo[4,3-b]pyridazine,
• 3-methyl-6-(4-{3-[(3S)-3-methylpiperidin-1-yl]propoxy}-phenyl]-pyrido[2,3-d][1,2,4]triazolo[4,3-b]pyridazine,
• 3-methyl-6-(4-{3-[(2R)-3-methylpyrrolidin-1-yl]propoxy}-phenyl]-pyrido[3,2-d][1,2,4]triazolo[4,3-b]pyridazine,
• 3-methyl-6-(4-{3-[(2R)-3-methylpyrrolidin-1-yl]propoxy}-phenyl]-pyrido[2,3-d][1,2,4]triazolo[4,3-b]pyridazine,
• 6-[4-(1-isopropylpiperidin-4-yloxy)phenyl]-3-methylpyrido[3,2-d][1,2,4]triazolo[4,3-b]pyridazine,
• 6-[4-(1-isopropylpiperidin-4-yloxy)phenyl]-3-methylpyrido[2,3-d][1,2,4]triazolo[4,3-b]pyridazine,
• 6-[4-(1-cyclobutylpiperidin-4-yloxy)phenyl]-3-methylpyrido[3,2-d][1,2,4]triazolo[4,3-b]pyridazine,
• 6-[4-(1-cyclobutylpiperidin-4-yloxy)phenyl]-3-methylpyrido[2,3-d][1,2,4]triazolo[4,3-b]pyridazine,
• 6-[4-(1-cyclopentylpiperidin-4-yloxy)phenyl]-3-methylpyrido[3,2-d][1,2,4]triazolo[4,3-b]pyridazine,
• 6-[4-(1-cyclopentylpiperidin-4-yloxy)phenyl]-3-methylpyrido[2,3-d][1,2,4]triazolo[4,3-b]pyridazine,
• 6-[4-(1-isopropylpiperidin-4-yloxy)phenyl]pyrido[3,2-d][1,2,4]triazolo[4,3-b]pyridazine,
• 6-[4-(1-isopropylpiperidin-4-yloxy)phenyl]pyrido[2,3-d][1,2,4]triazolo[4,3-b]pyridazine,
• 6-[4-(1-cyclobutylpiperidin-4-yloxy)phenyl]pyrido[3,2-d][1,2,4]triazolo[4,3-b]pyridazine,
• 6-[4-(1-cyclobutylpiperidin-4-yloxy)phenyl]pyrido[2,3-d][1,2,4]triazolo[4,3-b]pyridazine,
• 6-[4-(1-cyclopentylpiperidin-4-yloxy)phenyl]pyrido[3,2-d][1,2,4]triazolo[4,3-b]pyridazine,
• 6-[4-(1-cyclopentylpiperidin-4-yloxy)phenyl]pyrido[2,3-d][1,2,4]triazolo[4,3-b]pyridazine,
• 6-[6-(3-piperidin-1-ylpropoxy)pyridin-3-yl]-[1,2,4]triazolo[3,4-a]phthalazine, and
• 6-{6-[(3S)-3-piperidin-1-ylpropoxy]pyridin-3-yl]-[1,2,4]triazolo[3,4-a]phthalazine,
• or a pharmaceutically-acceptable salt thereof.