Patent Grant
8552031
1. Technical Field
The present invention relates to preventive, therapeutic and improving agents having affinity for and agonistic action on the thrombopoietin receptor for diseases against which activation of the thrombopoietin receptor is effective. Specifically, it relates to pharmaceutical compositions comprising compounds which increase platelets through stimulation of differentiation and proliferation of hematopoietic stem cells, megakaryocytic progenitor cells and megakaryocytes or compounds for therapeutic angiogenesis or with anti-arteriosclerosis action that stimulate differentiation and proliferation of vascular endothelial cells and endothelial progenitor cells.
2. Background Art
Thrombopoietin is a cytokine consisting of 332 amino acids that increases platelet production by stimulating differentiation and proliferation of hematopoietic stem cells, megakaryocytic progenitor cells and megakaryocytes mediated by its receptor and therefore is promising as a drug for hematological disorders. Recent reports that it stimulates differentiation and proliferation of vascular endothelial cells and endothelial progenitor cells have raised expectations of therapeutic angiogenesis, anti-arteriosclerosis and prevention of cardiovascular events (for example, non-patent document 1, non-patent document 2 and non-patent document 3).
Biologically active substances which have been known so far to regulate platelet production through the thrombopoietin receptor include, in addition to thrombopoietin itself, low molecular weight peptides having affinity for the thrombopoietin receptor (for example, patent document 1, patent document 2, patent document 3 and patent document 4).
As a result of search for nonpeptidic low molecular weight compounds that increase platelet production mediated by the thrombopoietin receptor, low molecular weight compounds having affinity for the thrombopoietin receptor have been reported (for example, patent document 5 to patent document 26).
Thrombopoietin and low molecular weight peptides having affinity for the thrombopoietin receptor are likely to be easily degraded in the gastrointestinal tract and are usually difficult to orally administer. As to thrombopoietin itself, the appearance of anti-thrombopoietin antibodies have been reported.
Besides, though it is probably possible to orally administer nonpeptidic low molecular weight compounds, no practical drugs have been put on the market.
Therefore, orally administrable low molecular weight compounds having excellent affinity for and agonistic action on the thrombopoietin receptor as preventive, therapeutic and improving agents for diseases against which activation of the thrombopoietin receptor is effective have been demanded. Specifically, low molecular, weight compounds which can serve as platelet increasing agents or increasing agents for other blood cells by stimulating differentiation and proliferation of hematopoietic stem cells, megakaryocytic progenitor cells and megakaryocytes or low molecular weight compounds which can be used for therapeutic angiogenesis or as preventive and therapeutic agents for arteriosclerosis by stimulating endothelial cells and endothelial progenitor cells have been demanded.
The present inventors conducted extensive research to find low molecular weight compounds having affinity for and agonistic action on the thrombopoietin receptor, and as a result, found that the compounds of the present invention have high affinity and agonistic action which enable them to show potent platelet increasing action by stimulating differentiation and proliferation of megakaryocytic progenitor cells and megakaryocytes. The present invention was accomplished on the basis of this discovery.
Namely, the present invention relates to:
1. A compound represented by the formula (1)
wherein A is a nitrogen atom or CR4 (wherein R4 is a hydrogen atom, a hydroxyl group (the hydroxyl group may be substituted with a C2-6 alkenyl group or a C2-6 alkynyl group), a thiol group (the thiol group may be substituted with a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group or a C1-10 alkylcarbonyl group), an amino group (the amino group may be substituted with one or two C2-6 alkenyl groups or one or two C2-6 alkynyl groups), a formyl group, a halogen atom, a nitro group, a cyano group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkylcarbonylamino group, a mono- or di-C1-10 alkylamino group, a C1-10 alkoxy group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkylcarbonylamino group, the mono- or di-C1-10 alkylamino group and the C1-10 alkoxy group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)), a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups), a C2-14 aryloxy group (the C2-14 aryloxy group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups), SO2R5, SOR5 or COR5 (wherein R5 is a hydroxyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C2-9 heterocyclic group, a C1-10 alkoxy group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C2-9 heterocyclic group and the C1-10 alkoxy group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)), a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with, one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups), a C2-14 aryloxy group (the C2-14 aryloxy group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups) or NR6R7 (wherein each of R6 and R7 is independently a hydrogen atom, a hydroxyl group, a formyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkylcarbonyloxy group, the C1-10 alkoxycarbonyl group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)) or a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups), or R6 and R7 mean, together with each other, —(CH2)m1-E-(CH2)m2— (wherein E is an oxygen atom, a sulfur atom, CR26R27 (wherein each of R26 and R27 is independently a hydrogen atom, a C1-10 alkyl group, a C2-14 aryl group, a C1-10 alkoxy group, a C2-14 aryloxy group, a hydroxyl group or a protected hydroxyl group) or NR8 (wherein R8 is a hydrogen atom, a hydroxyl group, a formyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkoxy group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkoxy group, the C1-10 alkylcarbonyloxy group, the C1-10 alkoxycarbonyl group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)) or a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups)), and each of m1 and m2 is independently an integer of from 0 to 5 provided that m1+m2 is 3, 4 or 5)))),
B is an oxygen atom, a sulfur atom or NR9 (wherein R9 is a hydrogen atom, a hydroxyl group, a formyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkoxy group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkoxy group, the C1-10 alkylcarbonyloxy group, the C1-10 alkoxycarbonyl group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms), or one or more halogen atoms)), a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups) or a C2-14 aryloxy group (the C2-14 aryloxy group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups)) (provided that when A is a nitrogen atom, B is not NH),
R1 is a C2-14 aryl group (the C2-14 aryl group may be substituted with one or more substituents selected from the group consisting of halogen atoms, carboxyl groups, nitro groups, formyl groups, cyano groups, hydroxyl groups, protected hydroxyl groups, C1-10 alkyl groups, C2-6 alkenyl groups, C2-6 alkynyl groups, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups (the C1-10 alkyl groups, the C2-6 alkenyl groups, the C2-6 alkynyl groups, the C1-10 alkoxy groups, the C1-10 alkylcarbonyl groups, the C1-10 alkylcarbonyloxy groups and the C1-10 alkoxycarbonyl groups may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)), C2-14 aryl groups (the C2-14 aryl groups may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups), thiol groups and amino groups (the thiol groups and the amino groups may be optionally substituted with one or two substituents selected from the group consisting of formyl groups, C1-10 alkyl groups, C2-6 alkenyl groups, C2-6 alkynyl groups and C1-10 alkylcarbonyl groups (the C1-10 alkyl groups, the C2-6 alkenyl groups, the C2-6 alkynyl groups and the C1-10 alkylcarbonyl groups may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)))),
L1 is a bond, CR10R11 (wherein each of R10 and R11 is independently a hydrogen atom or a C1-6 alkyl group (the C1-6 alkyl group may be substituted with one or more halogen atoms)), an oxygen atom, a sulfur atom or NR12 (wherein R12 is a hydrogen atom, a hydroxyl group, a formyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkoxy group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkoxy group, the C1-10 alkylcarbonyloxy group, the C1-10 alkoxycarbonyl group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)) or a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups)),
X is OR13, SR13 or NR14R15 (wherein R13 is a hydrogen atom, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group or a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)), and each of R14 and R15 is independently a hydrogen atom, a formyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkoxy group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkoxy group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)) or a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups)),
R2 is a hydrogen atom, a formyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkoxy group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkoxy group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)) or a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups),
L2 is a bond, CR34R35 (wherein each of R34 and R35 is independently a hydrogen atom or a C1-6 alkyl group (the C1-6 alkyl group may be substituted with one or more halogen atoms)), an oxygen atom, a sulfur atom or NR16 (wherein R16 is a hydrogen atom, a hydroxyl group, a formyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkoxy group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkoxy group, the C1-10 alkylcarbonyloxy group, the C1-10 alkoxycarbonyl group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)) or a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups)),
L3 is a bond, CR17R18 (wherein each of R17 and R18 is independently a hydrogen atom, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkoxy group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkoxy group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)) or a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups)), an oxygen atom, a sulfur atom or NR19 (wherein R19 is a hydrogen atom, a hydroxyl group, a formyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkoxy group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkylcarbonyloxy group, the C1-10 alkoxycarbonyl group, the C1-10 alkoxy group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)) or a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups)),
Y is an oxygen atom, a sulfur atom or NR23 (wherein R23 is a hydrogen atom, a hydroxyl group, a formyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkoxy group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkoxy group, the C1-10 alkylcarbonyloxy group, the C1-10 alkoxycarbonyl group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups, may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)) or a C2-14 aryl group (the C2-14 aryl group may be substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups)),
L4 is a bond, CR20R21 (wherein each of R20 and R21 is independently a hydrogen atom, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkoxy group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkoxy group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)) or a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms))), an oxygen atom, a sulfur atom or NR22 (wherein R22 is a hydrogen atom, a hydroxyl group, a protected hydroxyl group, a formyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkoxy group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkoxy group, the C1-10 alkylcarbonyloxy group, the C1-10 alkoxycarbonyl group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)) or a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms))), and
When L4 is a bond, R3 is a methyl group (the methyl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups, C2-10 alkenyl groups, C2-10 alkynyl groups, C2-9 heterocyclic groups, C1-10 alkoxy groups, C1-10 thioalkyl groups, C1-10 alkylcarbonyl groups, mono- or di-C1-10 alkylamino groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups (the C1-10 alkyl groups, the C2-10 alkenyl groups, the C2-10 alkynyl groups, the C2-9 heterocyclic groups, the C1-10 alkoxy groups, the C1-10 thioalkyl groups, the C1-10 alkylcarbonyl groups, the mono- or di-C1-10 alkylamino groups, the C1-10 alkylcarbonyloxy groups, the C1-10 alkoxycarbonyl groups and the C1-10 alkylcarbonylamino groups may be optionally substituted with one or more C2-14 aryl groups (the C2-14 aryl groups may be optionally substituted with one or more substituents independently represented by —W1 (CW2W3)mW4 (wherein W1 is (CR24R25)n (wherein each of R24 and R25 is independently a hydrogen atom or a C1-6 alkyl group (the C1-6 alkyl group may be substituted with one or more halogen atoms), or R24 and R25 mean, together with each other, O═ or S═, and n is 0, 1, 2 or 3), an oxygen atom, a sulfur atom or NR36 (wherein R36 is a hydrogen atom, a C1-6 alkyl group, a formyl group or a C1-6 alkylcarbonyl group), each of W2 and W3 is independently a hydrogen atom or a C1-3 alkyl group (the C1-3 alkyl group may be substituted with one or more halogen atoms), m is 0, 1, 2 or 3, and W4 is a hydroxyl group, a protected hydroxyl group, a thiol group, an amino group, a formyl group, a halogen atom, a nitro group, a cyano group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C2-9 heterocyclic group, a C1-10 alkoxy group, a C1-10 alkylcarbonyloxy group, a C1-10 alkylcarbonylamino group, a mono- or di-C1-10 alkylamino group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C2-9 heterocyclic group, the C1-10 alkoxy group, the C1-10 alkylcarbonyloxy group, the C1-10 alkylcarbonylamino group and the mono- or di-C1-10 alkylamino group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)), a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, thiol groups, phosphonic acid groups, sulfonic acid groups, tetrazole groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)), SO2R28, SOR28, COR28 (wherein R28 is a hydroxyl group, a protected hydroxyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C2-9 heterocyclic group, a C1-10 alkoxy group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C2-9 heterocyclic group and the C1-10 alkoxy group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)), a C2-14 aryl group, a C2-14 aryloxy group (the C2-14 aryl group and the C2-14 aryloxy group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)) or NR29R30 (wherein each of R29 and R30 is independently a hydrogen atom, a hydroxyl group, a protected hydroxyl group, a formyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkoxy group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylsulfonyl group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkoxy group, the C1-10 alkylcarbonyloxy group, the C1-10 alkoxycarbonyl group, the C1-10 alkylsulfonyl group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl group, sulfonyl groups, sulfamoyl groups, sulfo groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups (the C1-10 alkoxy groups may be substituted with one or more halogen atoms), C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms))) or a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl group, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)), or R29 and R30, together with each other means —(CH2)m3-G-(CH2)m4— (wherein G is an oxygen atom, a sulfur atom, CR31R32 (wherein each of R31 and R32 is independently a hydrogen atom, a C1-10 alkyl group, a C2-14 aryl group, a C1-10 alkoxy group, a C2-14 aryloxy group, a hydroxyl group or a protected hydroxyl group) or NR33 (wherein R33 is a hydrogen atom, a hydroxyl group, a formyl group, a C1-10 alkyl group, a C2-6 alkenyl group, C2-6 alkynyl group, a C1-10 alkoxy group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkoxy group, the C1-10 alkylcarbonyloxy group, the C1-10 alkoxycarbonyl group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)) or a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms))), and each of m3 and m4 is independently an integer of from 0 to 5, provided that m3+m4 is 3, 4 or 5))), a tetrazole group or a phosphonic acid group)) or one or more substituents independently represented by —W5(CW6W7)m10W8 (wherein W5, W6, W7 and m10 are the same as W1, W2, W3 and m, respectively, W1, W2, W3 and m are the same as defined above, and W8 is a hydroxyl group, a protected hydroxyl group, a thiol group, an amino group, a formyl group, a halogen atom, a nitro group, a cyano group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C2-9 heterocyclic group, a C1-10 alkoxy group, a C1-10 alkylcarbonyloxy group, a C1-10 alkylcarbonylamino group, a mono- or di-C1-10 alkylamino group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C2-9 heterocyclic group, the C1-10 alkoxy group, the C1-10 alkylcarbonyloxy group, the C1-10 alkylcarbonylamino group and the mono- or di-C1-10 alkylamino group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)), SO2R28a, SOR28a, COR28a (wherein R28a is the same as R28, and R28 is the same as defined above), a tetrazole group or a phosphonic acid group)) and substituents independently represented by —W9 (CW10W11)m11W12 (wherein W9, W10, W11, W12 and m11 are the same as W1, W2, W3, W8 and m, respectively, and W1, W2, W3, W8 and m are the same as defined above)), a C2-10 alkyl group, a C2-10 alkenyl group, a C2-10 alkynyl group or a C2-9 heterocyclic group (the C2-10 alkyl group, the C2-10 alkenyl group, the C2-10 alkynyl group and the C2-9 heterocyclic group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups, C2-10 alkenyl groups, C2-10 alkynyl groups, C2-9 heterocyclic groups, C1-10 alkoxy groups, C1-10 thioalkyl groups, C1-10 alkylcarbonyl groups, mono- or di-C1-10 alkylamino groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylsulfonyl groups, C1-10 alkylaminocarbonyl groups, C1-10 alkylaminosulfonyl groups, C1-10 dialkylaminocarbonyl groups, C1-10 alkylcarbonylamino groups (the C1-10 alkyl groups, the C2-10 alkenyl groups, the C2-10 alkynyl groups, the C2-9 heterocyclic groups, the C1-10 alkoxy groups, the C1-10 thioalkyl groups, the C1-10 alkylcarbonyl groups, the mono- or di-C1-10 alkylamino groups, the C1-10 alkylcarbonyloxy groups, the C1-10 alkoxycarbonyl groups, the C1-10 alkylsulfonyl groups, the C1-10 alkylaminocarbonyl groups, the C1-10 alkylaminosulfonyl groups, the C1-10 dialkylaminocarbonyl groups and the C1-10 alkylcarbonylamino groups may be optionally substituted with one or more C2-14 aryl groups (the C2-14 aryl groups may be optionally substituted with one or more substituents independently represented by —W1 (CW2W3)mW4 (wherein W1, W2, W3, W4 and m are the same as defined above)) or one or more substituents independently represented by —W5 (CW6W7)m10W8 (wherein W5, W6, W7, W8 and m10 are the same as defined above)), substituents independently represented by W9(CW10W11)m11W12 (wherein W9, W10, W11, W12 and m11 are the same as defined above) and C2-14 aryl groups (the C2-14 aryl groups may be optionally substituted with one or more substituents independently represented by —W13(CW14W15)m12W16 (wherein W13, W14, W15, W16 and m12 are the same as W1, W2, W3, W4 and m, respectively, and W1, W2, W3, W4 and m are the same as defined above))), or when L4 is CR20R21 (wherein each of R20 and R21 is independently a hydrogen atom, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkoxy group, a C1-10 alkylcarbonyl group, (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkoxy group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)) or a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms))), an oxygen atom, a sulfur atom or NR22 (wherein R22 is a hydrogen atom, a hydroxyl group, a protected hydroxyl group, a formyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkoxy group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkoxy group, the C1-10 alkylcarbonyloxy group, the C1-10 alkoxycarbonyl group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)) or a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms))), R3 is a C1-10 alkyl group, a C2-10 alkenyl group, a C2-10 alkynyl group, a C2-9 heterocyclic group, a C1-10 alkoxy group, a C1-10 thioalkyl group, a C1-10 alkylcarbonyl group, a mono- or di-C1-10 alkylamino group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group or a C1-10 alkylcarbonylamino group (the C1-10 alkyl group, the C2-10 alkenyl group, the C2-10 alkynyl group, the C2-9 heterocyclic group, the C1-10 alkoxy group, the C1-10 thioalkyl group, the C1-10 alkylcarbonyl group, the mono- or di-C1-10 alkylamino group, the C1-10 alkylcarbonyloxy group, the C1-10 alkoxycarbonyl group and the C1-10 alkylcarbonylamino group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups, C2-10 alkenyl groups, C2-10 alkynyl groups, C2-9 heterocyclic groups, C1-10 alkoxy groups, C1-10 thioalkyl groups, C1-10 alkylcarbonyl groups, mono- or di-C1-10 alkylamino groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups (the C1-10 alkyl groups, the C2-10 alkenyl groups, the C2-10 alkynyl groups, the C2-9 heterocyclic groups, the C1-10 alkoxy groups, the C1-10 thioalkyl groups, the C1-10 alkylcarbonyl groups, the mono- or di-C1-10 alkylamino groups, the C1-10 alkylcarbonyloxy groups, the C1-10 alkoxycarbonyl groups and the C1-10 alkylcarbonylamino groups may be optionally substituted with one or more C2-14 aryl groups (the C2-14 aryl groups may be optionally substituted with one or more substituents independently represented by —W1(CW2W3)mW4 (wherein W1, W2, W3, W4 and m are the same as defined above)) or one or more substituents independently represented by —W5(CW6W7)m10W8 (wherein W5, W6, W7, W8 and m10 are the same as defined above)), substituents independently represented by —W9(CW10W11)m11W12 (wherein W9, W10, W11, W12 and m11 are the same as defined above) and C2-14 aryl groups (the C2-14 aryl groups may be optionally substituted with one or more substituents independently represented by —W13(CW14W15)m12W16 (wherein W13, W14, W15, W16 and m12 are the same as defined above))), a tautomer, prodrug or pharmaceutically acceptable salt of the compound or a solvate thereof.
2. The compound according to 1, wherein L4 is a bond, R3 is a methyl group (the methyl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups, C2-10 alkenyl groups, C2-10 alkynyl groups, C2-9 heterocyclic groups, C1-10 alkoxy groups, C1-10 thioalkyl groups, C1-10 alkylcarbonyl groups, mono- or di-C1-10 alkylamino groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups (the C1-10 alkyl groups, the C2-10 alkenyl groups, the C2-10 alkynyl groups, the C2-9 heterocyclic groups, the C1-10 alkoxy groups, the C1-10 thioalkyl groups, the C1-10 alkylcarbonyl groups, the mono- or di-C1-10 alkylamino groups, the C1-10 alkylcarbonyloxy groups, the C1-10 alkoxycarbonyl groups and the C1-10 alkylcarbonylamino groups may be optionally substituted with one or more C2-14 aryl groups (the C2-14 aryl groups may be optionally substituted with one or more substituents independently represented by —W1 (CW2W3)mW4 (wherein W1 is (CR24R25)n (wherein each of R24 and R25 is independently a hydrogen atom or a C1-6 alkyl group (the C1-6 alkyl group may be substituted with one or more halogen atoms), or R24 and R25 mean, together with each other, O═ or S═, and n is 0, 1, 2 or 3), an oxygen atom, a sulfur atom or NR36 (wherein R36 is a hydrogen atom, a C1-6 alkyl group, a formyl group or a C1-6 alkylcarbonyl group), each of W2 and W3 is independently a hydrogen atom or a C1-3 alkyl group (the C1-3 alkyl group may be substituted with one or more halogen atoms), m is 0, 1, 2 or 3, and W4 is a hydroxyl group, a protected hydroxyl group, a thiol group, an amino group, a formyl group, a halogen atom, a nitro group, a cyano group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C2-9 heterocyclic group, a C1-10 alkoxy group, a C1-10 alkylcarbonyloxy group, a C1-10 alkylcarbonylamino group, a mono- or di-C1-10 alkylamino group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C2-9 heterocyclic group, the C1-10 alkoxy group, the C1-10 alkylcarbonyloxy group, the C1-10 alkylcarbonylamino group and the mono- or di-C1-10 alkylamino group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)), a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, thiol groups, phosphonic acid groups, sulfonic acid groups, tetrazole groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)), SO2R28, SOR28, COR28 (wherein R28 is a hydroxyl group, a protected hydroxyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C2-9 heterocyclic group, a C1-10 alkoxy group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C2-9 heterocyclic group and the C1-10 alkoxy group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)), a C2-14 aryl group, a C2-14 aryloxy group (the C2-14 aryl group and the C2-14 aryloxy group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)) or NR29R30 (wherein each of R29 and R30 is independently a hydrogen atom, a hydroxyl group, a protected hydroxyl group, a formyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkoxy group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylsulfonyl group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkoxy group, the C1-10 alkylcarbonyloxy group, the C1-10 alkoxycarbonyl group, the C1-10 alkylsulfonyl group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl group, sulfonyl groups, sulfamoyl groups, sulfo groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups (the C1-10 alkoxy groups may be substituted with one or more halogen atoms), C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms))) or a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl group, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)), or R29 and R30, together with each other means —(CH2)m3-G-(CH2)m4— (wherein G is an oxygen atom, a sulfur atom, CR31R32 (wherein each of R31 and R32 is independently a hydrogen atom, a C1-10 alkyl group, a C2-14 aryl group, a C1-10 alkoxy group, a C2-14 aryloxy group, a hydroxyl group or a protected hydroxyl group) or NR33 (wherein R33 is a hydrogen atom, a hydroxyl group, a formyl group, a C1-10 alkyl group, a C2-6 alkenyl group, C2-6 alkynyl group, a C1-10 alkoxy group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkoxy group, the C1-10 alkylcarbonyloxy group, the C1-10 alkoxycarbonyl group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)) or a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms))), and each of m3 and m4 is independently an integer of from 0 to 5, provided that m3+m4 is 3, 4 or 5))), a tetrazole group or a phosphonic acid group)) or one or more substituents independently represented by —W5(CW6W7)m10W8 (wherein W5, W6, W7 and m10 are the same as W1, W2, W3 and m, respectively, W1, W2, W3 and m are the same as defined above, and W8 is a hydroxyl group, a protected hydroxyl group, a thiol group, an amino group, a formyl group, a halogen atom, a nitro group, a cyano group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C2-9 heterocyclic group, a C1-10 alkoxy group, a C1-10 alkylcarbonyloxy group, a C1-10 alkylcarbonylamino group, a mono- or di-C1-10 alkylamino group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C2-9 heterocyclic group, the C1-10 alkoxy group, the C1-10 alkylcarbonyloxy group, the C1-10 alkylcarbonylamino group and the mono- or di-C1-10 alkylamino group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)), SO2R28a, SOR28a, COR28a (wherein R28a is the same as R28, and R28 is the same as defined above), a tetrazole group or a phosphonic acid group)) and substituents independently represented by —W9(CW10W11)m11W12 (wherein W9, W10, W11, W12 and m11 are the same as W1, W2, W3, W8 and m, respectively, and W1, W2, W3, W8 and m are the same as defined above)), a C2-10 alkyl group, a C2-10 alkenyl group, a C2-10 alkynyl group or a C2-9 heterocyclic group (the C2-10 alkyl group, the C2-10 alkenyl group, the C2-10 alkynyl group and the C2-9 heterocyclic group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups, C2-10 alkenyl groups, C2-10 alkynyl groups, C2-9 heterocyclic groups, C1-10 alkoxy groups, C1-10 thioalkyl groups, C1-10 alkylcarbonyl groups, mono- or di-C1-10 alkylamino groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylaminocarbonyl groups, C1-10 dialkylaminocarbonyl groups, C1-10 alkylcarbonylamino groups (the C1-10 alkyl groups, the C2-10 alkenyl groups, the C2-10 alkynyl groups, the C2-9 heterocyclic groups, the C1-10 alkoxy groups, the C1-10 thioalkyl groups, the C1-10 alkylcarbonyl groups, the mono- or di-C1-10 alkylamino groups, the C1-10 alkylcarbonyloxy groups, the C1-10 alkoxycarbonyl groups, the C1-10 alkylaminocarbonyl groups, the C1-10 dialkylaminocarbonyl groups and the C1-10 alkylcarbonylamino groups may be optionally substituted with one or more C2-14 aryl groups (the C2-14 aryl groups may be optionally substituted with one or more substituents independently represented by —W1(CW2W3)mW4 (wherein W1, W2, W3, W4 and m are the same as defined above)) or one or more substituents independently represented by —W5 (CW6W7)m10W8 (wherein W5, W6, W7, W8 and m10 are the same as defined above)), substituents independently represented by W9(CW10W11)m11W12 (wherein W9, W10, W11, W12 and m11 are the same as defined above) and C2-14 aryl groups (the C2-14 aryl groups may be optionally substituted with one or more substituents independently represented by —W13(CW14W15)m12W16 (wherein W13, W14, W15, W16 and m12 are the same as W1, W2, W3, W4 and m, respectively, and W1, W2, W3, W4 and m are the same as defined above))), a tautomer, prodrug or pharmaceutically acceptable salt of the compound or a solvate thereof.
3. The compound according to 1, wherein L4 is CR20R21 (wherein each of R20 and R21 is independently a hydrogen atom, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkoxy group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkoxy group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)) or a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms))), an oxygen atom, a sulfur atom or NR22 (wherein R22 is a hydrogen atom, a hydroxyl group, a protected hydroxyl group, a formyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkoxy group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkoxy group, the C1-10 alkylcarbonyloxy group, the C1-10 alkoxycarbonyl group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)) or a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms))), and R3 is a C1-10 alkyl group, a C2-10 alkenyl group, a C2-10 alkynyl group, a C2-9 heterocyclic group, a C1-10 alkoxy group, a C1-10 thioalkyl group, a C1-10 alkylcarbonyl group, a mono- or di-C1-10 alkylamino group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group or a C1-10 alkylcarbonylamino group (the C1-10 alkyl group, the C2-10 alkenyl group, the C2-10 alkynyl group, the C2-9 heterocyclic group, the C1-10 alkoxy group, the C1-10 thioalkyl group, the C1-10 alkylcarbonyl group, the mono- or di-C1-10 alkylamino group, the C1-10 alkylcarbonyloxy group, the C1-10 alkoxycarbonyl group and the C1-10 alkylcarbonylamino group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups, C2-10 alkenyl groups, C2-10 alkynyl groups, C2-9 heterocyclic groups, C1-10 alkoxy groups, C1-10 thioalkyl groups, C1-10 alkylcarbonyl groups, mono- or di-C1-10 alkylamino groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups (the C1-10 alkyl groups, the C2-10 alkenyl groups, the C2-10 alkynyl groups, the C2-9 heterocyclic groups, the C1-10 alkoxy groups, the C1-10 thioalkyl groups, the C1-10 alkylcarbonyl groups, the mono- or di-C1-10 alkylamino groups, the C1-10 alkylcarbonyloxy groups, the C1-10 alkoxycarbonyl groups and the C1-10 alkylcarbonylamino groups may be optionally substituted with one or more C2-14 aryl groups (the C2-14 aryl groups may be optionally substituted with one or more substituents independently represented by —W1(CW2W3)mW4 (wherein W1 is (CR24R25)n (wherein each of R24 and R25 is independently a hydrogen atom or a C1-6 alkyl group (the C1-6 alkyl group may be substituted with one or more halogen atoms), or R24 and R25 mean, together with each other, O═ or S═, and n is 0, 1, 2 or 3), an oxygen atom, a sulfur atom or NR36 (wherein R36 is a hydrogen atom, a C1-6 alkyl group, a formyl group or a C1-6 alkylcarbonyl group), each of W2 and W3 is independently a hydrogen atom or a C1-3 alkyl group (the C1-3 alkyl group may be substituted with one or more halogen atoms), m is 0, 1, 2 or 3, and W4 is a hydroxyl group, a protected hydroxyl group, a thiol group, an amino group, a formyl group, a halogen atom, a nitro group, a cyano group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C2-9 heterocyclic group, a C1-10 alkoxy group, a C1-10 alkylcarbonyloxy group, a C1-10 alkylcarbonylamino group, a mono- or di-C1-10 alkylamino group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C2-9 heterocyclic group, the C1-10 alkoxy group, the C1-10 alkylcarbonyloxy group, the C1-10 alkylcarbonylamino group and the mono- or di-C1-10 alkylamino group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)), a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, thiol groups, phosphonic acid groups, sulfonic acid groups, tetrazole groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)), SO2R28, SOR28, COR28 (wherein R28 is a hydroxyl group, a protected hydroxyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C2-9 heterocyclic group, a C1-10 alkoxy group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C2-9 heterocyclic group and the C1-10 alkoxy group may be optionally substituted with one or more substituents selected from the group, consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)), a C2-14 aryl group, a C2-14 aryloxy group (the C2-14 aryl group and the C2-14 aryloxy group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)) or NR29R30 (wherein each of R29 and R30 is independently a hydrogen atom, a hydroxyl group, a protected hydroxyl group, a formyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkoxy group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylsulfonyl group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkoxy group, the C1-10 alkylcarbonyloxy group, the C1-10 alkoxycarbonyl group, the C1-10 alkylsulfonyl group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)) or a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl group, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)), or R29 and R30, together with each other means —(CH2)m3-G-(CH2)m4— (wherein G is an oxygen atom, a sulfur atom, CR31R32 (wherein each of R31 and R32 is independently a hydrogen atom, a C1-10 alkyl group, a C2-14 aryl group, a C1-10 alkoxy group, a C2-14 aryloxy group, a hydroxyl group or a protected hydroxyl group) or NR33 (wherein R33 is a hydrogen atom, a hydroxyl group, a formyl group, a C1-10 alkyl group, a C2-6 alkenyl group, C2-6 alkynyl group, a C1-10 alkoxy group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkoxy group, the C1-10 alkylcarbonyloxy group, the C1-10 alkoxycarbonyl group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)) or a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms))), and each of m3 and m4 is independently an integer of from 0 to 5, provided that m3+m4 is 3, 4 or 5))), a tetrazole group or a phosphonic acid group)) or one or more substituents independently represented by —W5(CW6W7)m10W8 (wherein W5, W6, W7 and m10 are the same as W1, W2, W3 and m, respectively, W1, W2, W3 and m are the same as defined above, and W is a hydroxyl group, a protected hydroxyl group, a thiol group, an amino group, a formyl group, a halogen atom, a nitro group, a cyano group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C2-9 heterocyclic group, a C1-10 alkoxy group, a C1-10 alkylcarbonyloxy group, a C1-10 alkylcarbonylamino group, a mono- or di-C1-10 alkylamino group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C2-9 heterocyclic group, the C1-10 alkoxy group, the C1-10 alkylcarbonyloxy group, the C1-10 alkylcarbonylamino group and the mono- or di-C1-10 alkylamino group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)), SO2R28a, SOR28a, COR28a (wherein R28a is the same as R28, and R28 is the same as defined above), a tetrazole group or a phosphonic acid group)), substituents independently represented by —W9(CW10W11)m11W12 (wherein W9, W10, W11, W12 and m11 are the same as W1, W2, W3, W8 and m, respectively, and W1, W2, W3, W8 and m are the same as defined above) and C2-14 aryl groups (the C2-14 aryl groups may be optionally substituted with one or more substituents independently represented by —W13(CW14W15)m12W16 (wherein W13, W14, W15, W16 and m12 are the same as W1, W2, W3, W4 and m, respectively, and W1, W2, W3, W4 and m are the same as defined above))), a tautomer, prodrug or pharmaceutically acceptable salt of the compound or a solvate thereof.
4. The compound according to any one of 1 to 3, wherein
A is a nitrogen atom, and B is a sulfur atom, a tautomer, prodrug or pharmaceutically acceptable salt of the compound or a solvate thereof.
5. The compound according to any one of 1 to 3, wherein A is a nitrogen atom, and B is an oxygen atom, a tautomer, prodrug or pharmaceutically acceptable salt of the compound or a solvate thereof.
6. The compound according to any one of 1 to 3, wherein A is a nitrogen atom, and B is NR9 other than NH (wherein R9 is a hydrogen, atom, a hydroxyl group, a formyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkoxy group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkoxy group, the C1-10 alkylcarbonyloxy group, the C1-10 alkoxycarbonyl group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)), a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups) or a C2-14 aryloxy group (the C2-14 aryloxy group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups)), a tautomer, prodrug or pharmaceutically acceptable salt of the compound or a solvate thereof.
7. The compound according to any one of 1 to 3, wherein A is CR4 (wherein R4 is a hydrogen atom, a hydroxyl group (the hydroxyl group may be substituted with a C2-6 alkenyl group or a C2-6 alkynyl group), a thiol group (the thiol group may be substituted with a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group or a C1-10 alkylcarbonyl group), an amino group (the amino group may be substituted with one or two C2-6 alkenyl groups or one or two C2-6 alkynyl groups), a formyl group, a halogen atom, a nitro group, a cyano group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkylcarbonylamino group, a mono- or di-C1-10 alkylamino group, a C1-10 alkoxy group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkylcarbonylamino group, the mono- or di-C1-10 alkylamino group and the C1-10 alkoxy group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)), a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups), a C2-14 aryloxy group (the C2-14 aryloxy group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups), SO2R5, SOR5 or COR5 (wherein R5 is a hydroxyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C2-9 heterocyclic group, a C1-10 alkoxy group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C2-9 heterocyclic group and the C1-10 alkoxy group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)), a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups), a C2-14 aryloxy group (the C2-14 aryloxy group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups) or NR6R7 (wherein each of R6 and R7 is independently a hydrogen atom, a hydroxyl group, a formyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkylcarbonyloxy group, the C1-10 alkoxycarbonyl group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)) or a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups), or R6 and R7 mean, together with each other, —(CH2)m1-E-(CH2)m2— (wherein E is an oxygen atom, a sulfur atom, CR26R27 (wherein each of R26 and R27 is independently a hydrogen atom, a C1-10 alkyl group, a C2-14 aryl group, a C1-10 alkoxy group, a C2-14 aryloxy group, a hydroxyl group or a protected hydroxyl group) or NR8 (wherein R8 is a hydrogen atom, a hydroxyl group, a formyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkoxy group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkoxy group, the C1-10 alkylcarbonyloxy group, the C1-10 alkoxycarbonyl group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)) or a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups)), and each of m1 and m2 is independently an integer of from 0 to 5 provided that m1+m2 is 3, 4 or 5)))), and B is an oxygen atom, a tautomer, prodrug or pharmaceutically acceptable salt of the compound or a solvate thereof.
8. The compound according to any one of 1 to 3, wherein A is CR4 (wherein R4 is a hydrogen atom, a hydroxyl group (the hydroxyl group may be substituted with a C2-6 alkenyl group or a C2-6 alkynyl group), a thiol group (the thiol group may be substituted with a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group or a C1-10 alkylcarbonyl group), an amino group (the amino group may be substituted with one or two C2-6 alkenyl groups or one or two C2-6 alkynyl groups), a formyl group, a halogen atom, a nitro group, a cyano group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkylcarbonylamino group, a mono- or di-C1-10 alkylamino group, a C1-10 alkoxy group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkylcarbonylamino group, the mono- or di-C1-10 alkylamino group and the C1-10 alkoxy group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)), a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups), a C2-14 aryloxy group (the C2-14 aryloxy group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups), SO2R5, SOR5 or COR5 (wherein R5 is a hydroxyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C2-9 heterocyclic group, a C1-10 alkoxy group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C2-9 heterocyclic group and the C1-10 alkoxy group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)), a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups), a C2-14 aryloxy group (the C2-14 aryloxy group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups) or NR6R7 (wherein each of R6 and R7 is independently a hydrogen atom, a hydroxyl group, a formyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkylcarbonyloxy group, the C1-10 alkoxycarbonyl group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)) or a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups), or R6 and R7 mean, together with each other, —(CH2)m1-E-(CH2)m2— (wherein E is an oxygen atom, a sulfur atom, CR26R27 (wherein each of R26 and R27 is independently a hydrogen atom, a C1-10 alkyl group, a C2-14 aryl group, a C1-10 alkoxy group, a C2-14 aryloxy group, a hydroxyl group or a protected hydroxyl group) or NR8 (wherein R8 is a hydrogen atom, a hydroxyl group, a formyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkoxy group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkoxy group, the C1-10 alkylcarbonyloxy group, the C1-10 alkoxycarbonyl group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)) or a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups)), and each of m1 and m2 is independently an integer of from 0 to 5 provided that m1+m2 is 3, 4 or 5)))), and B is a sulfur atom, a tautomer, prodrug or pharmaceutically acceptable salt of the compound or a solvate thereof.
9. The compound according to any one of 1 to 3, wherein A is CR4 (wherein R4 is a hydrogen atom, a hydroxyl group (the hydroxyl group may be substituted with a C2-6 alkenyl group or a C2-6 alkynyl group), a thiol group (the thiol group may be substituted with a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group or a C1-10 alkylcarbonyl group), an amino group (the amino group may be substituted with one or two C2-6 alkenyl groups or one or two C2-6 alkynyl groups), a formyl group, a halogen atom, a nitro group, a cyano group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkylcarbonylamino group, a mono- or di-C1-10 alkylamino group, a C1-10 alkoxy group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkylcarbonylamino group, the mono- or di-C1-10 alkylamino group and the C1-10 alkoxy group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)), a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C2-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups), a C2-14 aryloxy group (the C2-14 aryloxy group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups), SO2R5, SOR5 or COR5 (wherein R5 is a hydroxyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C2-9 heterocyclic group, a C1-10 alkoxy group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C2-9 heterocyclic group and the C1-10 alkoxy group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)), a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups), a C2-14 aryloxy group (the C2-14 aryloxy group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups) or NR6R7 (wherein each of R6 and R7 is independently a hydrogen atom, a hydroxyl group, a formyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkylcarbonyloxy group, the C1-10 alkoxycarbonyl group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)) or a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups), or R6 and R7 mean, together with each other, —(CH2)m1-E-(CH2)m2— (wherein E is an oxygen atom, a sulfur atom, CR26R27 (wherein each of R26 and R27 is independently a hydrogen atom, a C1-10 alkyl group, a C2-14 aryl group, a C1-10 alkoxy group, a C2-14 aryloxy group, a hydroxyl group or a protected hydroxyl group) or NR8 (wherein R8 is a hydrogen atom, a hydroxyl group, a formyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkoxy group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkoxy group, the C1-10 alkylcarbonyloxy group, the C1-10 alkoxycarbonyl group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)) or a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups)), and each of m1 and m2 is independently an integer of from 0 to 5 provided that m1+m2 is 3, 4 or 5)))), and B is NR9 (wherein R9 is a hydrogen atom, a hydroxyl group, a formyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkoxy group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkoxy group, the C1-10 alkylcarbonyloxy group, the C1-10 alkoxycarbonyl group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)), a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups) or a C2-14 aryloxy group (the C2-14 aryloxy group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups)), a tautomer, prodrug or pharmaceutically acceptable salt of the compound or a solvate thereof.
10. The compound according to any one of 1 to 9, wherein L1 is a bond, a tautomer, prodrug or pharmaceutically acceptable salt of the compound or a solvate thereof.
11. The compound according to any one of 1 to 10, wherein L2 is a bond, a tautomer, prodrug or pharmaceutically acceptable salt of the compound or a solvate thereof.
12. The compound according to any one of 1 to 11, wherein L3 is NR19 (wherein R19 is a hydrogen atom, a hydroxyl group, a formyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkoxy group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkylcarbonyloxy group, the C1-10 alkoxycarbonyl group, the C1-10 alkoxy group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)) or a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups)), a tautomer, prodrug or pharmaceutically acceptable salt of the compound or a solvate thereof.
13. The compound according to any one of 1 to 11, wherein L3 is NH, a tautomer, prodrug or pharmaceutically acceptable salt of the compound or a solvate thereof.
14. The compound according to any one of 3 to 11, wherein L3 is the same as defined in 12, and L4 is NR22 (wherein R22 is a hydrogen atom, a hydroxyl group, a formyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkoxy group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkoxy group, the C1-10 alkylcarbonyloxy group, the C1-10 alkoxycarbonyl group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)) or a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups)), a tautomer, prodrug or pharmaceutically acceptable salt of the compound or a solvate thereof.
15. The compound according to any one of 3 to 11, wherein L3 is the same as defined in 13, and L4 is NR22 (wherein R22 is a hydrogen atom, a hydroxyl group, a formyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkoxy group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkoxy group, the C1-10 alkylcarbonyloxy group, the C1-10 alkoxycarbonyl group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)) or a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups)), a tautomer, prodrug or pharmaceutically acceptable salt of the compound or a solvate thereof.
16. The compound according to 14 or 15, wherein L4 is NH, a tautomer, prodrug or pharmaceutically acceptable salt of the compound or a solvate thereof.
17. The compound according to any one of 2 and 4 to 11, wherein L3 is the same as defined in 12, and L4 is a bond, a tautomer, prodrug or pharmaceutically acceptable salt of the compound or a solvate thereof.
18. The compound according to any one of 2 and 4 to 11, wherein L3 is the same as defined in 13, and L4 is a bond, a tautomer, prodrug or pharmaceutically acceptable salt of the compound or a solvate thereof.
19. The compound according to any one of 14 to 18, wherein Y is an oxygen atom, a tautomer, prodrug or pharmaceutically acceptable salt of the compound or a solvate thereof.
20. The compound according to any one of 14 to 18, wherein Y is a sulfur atom, a tautomer, prodrug or pharmaceutically acceptable salt of the compound or a solvate thereof.
21. The compound according to 19 or 20, wherein X is a hydroxyl group, a tautomer, prodrug or pharmaceutically acceptable salt of the compound or a solvate thereof.
22. The compound according to any one of 19 to 21, wherein R3 is a C2-9 heterocyclic group (the C2-9 heterocyclic group may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl groups, amino groups, carboxyl groups, phosphonic acid groups, sulfonic acid groups, carbamoyl groups, sulfamoyl groups, tetrazole groups, C1-10 alkoxycarbonyl groups, C1-10 alkoxy groups, C1-10 thioalkyl groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkylcarbonylamino groups and mono- or di-C1-10 alkylamino groups), a tautomer, prodrug or pharmaceutically acceptable salt of the compound or a solvate thereof.
23. The compound according to any one of 19 to 21, wherein R3 is a C2-9 heterocyclic group (the C2-9 heterocyclic group is substituted with a substituent selected from the group consisting of a hydroxyl group, an amino group, a carboxyl group, a phosphonic acid group, a sulfonic acid group, a carbamoyl group, a sulfamoyl group, a tetrazole group and a C1-10 alkoxycarbonyl group and with a substituent selected from the group consisting of a hydroxyl group, an amino group, a carboxyl group, a phosphonic acid group, a sulfonic acid group, a carbamoyl group, a sulfamoyl group, a tetrazole group, a C1-10 alkoxycarbonyl group, a nitro group, a cyano group, a halogen atom, a C1-10 alkyl group, a C1-10 alkyl group substituted with one or more fluorine atoms, a sulfamoyl group substituted with a C1-10 alkyl group, a carbamoyl group substituted with a C1-10 alkyl group and a C1-10 alkylcarbonylamino group), a tautomer, prodrug or pharmaceutically acceptable salt of the compound or a solvate thereof.
24. The compound according to any one of 19 to 21, wherein R3 is a C1-10 alkyl group or a C2-10 alkenyl group (the C1-10 alkyl group and the C2-10 alkenyl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups, C2-10 alkenyl groups, C1-10 alkoxy groups, C1-10 thioalkyl groups, C1-10 alkylcarbonyl groups, mono- or di-C1-10 alkylamino groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups (the C1-10 alkyl groups, the C2-10 alkenyl groups, the C1-10 alkoxy groups, the C1-10 thioalkyl groups, the C1-10 alkylcarbonyl groups, the mono- or di-C1-10 alkylamino groups, the C1-10 alkylcarbonyloxy groups, the C1-10 alkoxycarbonyl groups and the C1-10 alkylcarbonylamino groups may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl groups, amino groups, carboxyl groups, phosphonic acid groups, sulfonic acid groups, carbamoyl groups, sulfamoyl groups, tetrazole groups, C1-10 alkoxycarbonyl groups, C1-10 alkoxy groups, C1-10 thioalkyl groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkylcarbonylamino groups and mono- or di-C1-10 alkylamino groups), nitro group, halogen atoms, hydroxyl groups, amino groups, carboxyl groups, phosphonic acid groups, sulfonic acid groups, carbamoyl groups, sulfamoyl groups and tetrazole groups), a tautomer, prodrug or pharmaceutically acceptable salt of the compound or a solvate thereof.
25. The compound according to any one of 19 to 21, wherein R3 is a C1-10 alkyl group or a C2-10 alkenyl group (the C1-10 alkyl group and the C2-10 alkenyl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups, C2-6 alkenyl groups, C1-10 alkoxy groups, C1-10 thioalkyl groups, C1-10 alkylcarbonyl groups, mono- or di-C1-10 alkylamino groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups (the C1-10 alkyl groups, the C2-6 alkenyl groups, the C1-10 alkoxy groups, the C1-10 thioalkyl groups, the C1-10 alkylcarbonyl groups, the mono- or di-C1-10 alkylamino groups, the C1-10 alkylcarbonyloxyl groups, the C1-10 alkoxycarbonyl groups and the C1-10 alkylcarbonylamino groups may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl groups, amino groups, carboxyl groups, phosphonic acid groups, sulfonic acid groups, carbamoyl groups, sulfamoyl groups and tetrazole groups), halogen atoms, nitro groups, hydroxyl groups, amino groups, carboxyl groups, phosphonic acid groups, sulfonic acid groups, carbamoyl groups, sulfamoyl groups and tetrazole groups), a tautomer, prodrug or pharmaceutically acceptable salt of the compound or a solvate thereof.
26. The compound according to any one of 19 to 21, wherein R3 is a C2-9 heterocyclic group (the C2-9 heterocyclic group is substituted with one or more substituents selected from the group consisting of hydroxyl groups, amino groups, halogen atoms, carboxyl groups, sulfonic acid groups, carbamoyl groups, hydroxycarbamoyl groups, cyanocarbamoyl groups, sulfamoyl groups, hydroxysulfamoyl groups, cyanosulfamoyl groups, thiocarbamoyl groups, —CH2COOH, —OCH2COOH, —NHCH2COOH, —CH2OH, —OCH2OH, —NHCH2OH, —CH2CH2OH, —(C═O)COOH, —CH2 (C═O)COOH, —NH(C═O)COOH, —NHSO2NH2, C1-10 alkyl groups, C1-10 alkylsulfonyl groups, C1-10 alkylaminosulfonyl groups, C1-10 alkylcarbonyl groups, C1-10 alkylaminocarbonyl groups and C1-10 dialkylaminocarbonyl groups (the C1-10 alkyl groups, the C1-10 alkylsulfonyl groups, the C1-10 alkylaminosulfonyl groups, the C1-10 alkylcarbonyl groups, the C1-10 alkylaminocarbonyl groups and the C1-10 dialkylaminocarbonyl groups may be substituted with one or more substituents selected from the group consisting of phenyl groups, thienyl groups, furyl groups, pyridyl groups, nitro groups, cyano groups, hydroxyl groups, amino groups, carboxyl groups, phosphonic acid groups, sulfonic acid groups, carbamoyl groups, sulfamoyl groups and tetrazole groups)), a tautomer, prodrug or pharmaceutically acceptable salt of the compound or a solvate thereof.
27. The thrombopoietin receptor activator according to any one of 1 to 26.
28. A preventive, therapeutic or improving agent for diseases against which activation of the thrombopoietin receptor is effective, which contains the thrombopoietin receptor activator according to 27, a tautomer, prodrug or pharmaceutically acceptable salt of the activator or a solvate thereof, as an active ingredient.
29. A platelet increasing agent containing the thrombopoietin receptor activator according to 27, a tautomer, prodrug or pharmaceutically acceptable salt of the activator or a solvate thereof, as an active ingredient.
30. Medicament containing the compound according to any one of 1 to 26, a tautomer, prodrug or pharmaceutically acceptable salt of the compound or a solvate thereof, as an active ingredient.
The present invention provides pharmaceutical compositions comprising compounds which increase platelets through stimulation of differentiation and proliferation of hematopoietic stem cells, megakaryocytic progenitor cells and megakaryocytes or compounds for therapeutic angiogenesis or with anti-arteriosclerosis action that stimulate differentiation and proliferation of vascular endothelial cells and endothelial progenitor cells.
Now, the present invention will be described in detail.
In the present invention, “n” denotes normal, “i” denotes iso, “s” denotes secondary, “t” denotes tertiary, “c” denotes cyclo, “o” denotes ortho, “m” denotes meta, “p” denotes para, “Ph” denotes phenyl, “Py” denotes pyridyl, “Naphthyl” denotes naphthyl, “Me” denotes methyl, “Et” denotes ethyl, “Pr” denotes propyl, “Bu” denotes butyl and “Ac” denotes acetyl.
First, the terms, in the respective substituents R1 to R36 will be explained.
As a halogen atom, a fluorine atom, a chlorine atom, a bromine atom or an iodine atom may be mentioned.
A C1-3 alkyl group may be linear, branched or a C3 cycloalkyl group, and methyl, ethyl, n-propyl, i-propyl and c-propyl and the like may be mentioned.
A C1-6 alkyl group may be linear, branched or a C3-6 cycloalkyl group, and in addition to those mentioned above, n-butyl, i-butyl, s-butyl, t-butyl, c-butyl, 1-methyl-c-propyl, 2-methyl-c-propyl, n-pentyl, 1-methyl-n-butyl, 2-methyl-n-butyl, 3-methyl-n-butyl, 1,1-dimethyl-n-propyl, 1,2-dimethyl-n-propyl, 2,2-dimethyl-n-propyl, 1-ethyl-n-propyl, c-pentyl, 1-methyl-c-butyl, 2-methyl-c-butyl, 3-methyl-c-butyl, 1,2-dimethyl-c-propyl, 2,3-dimethyl-c-propyl, 1-ethyl-c-propyl, 2-ethyl-c-propyl, n-hexyl, 1-methyl-n-pentyl, 2-methyl-n-pentyl, 3-methyl-n-pentyl, 4-methyl-n-pentyl, 1,1-dimethyl-n-butyl, 1,2-dimethyl-n-butyl, 1,3-dimethyl-n-butyl, 2,2-dimethyl-n-butyl, 2,3-dimethyl-n-butyl, 3,3-dimethyl-n-butyl, 1-ethyl-n-butyl, 2-ethyl-n-butyl, 1,1,2-trimethyl-n-propyl, 1,2,2-trimethyl-n-propyl, 1-ethyl-1-methyl-n-propyl, 1-ethyl-2-methyl-n-propyl, c-hexyl, 1-methyl-c-pentyl, 2-methyl-c-pentyl, 3-methyl-c-pentyl, 1-ethyl-c-butyl, 2-ethyl-c-butyl, 3-ethyl-c-butyl, 1,2-dimethyl-c-butyl, 1,3-dimethyl-c-butyl, 2,2-dimethyl-c-butyl, 2,3-dimethyl-c-butyl, 2,4-dimethyl-c-butyl, 3,3-dimethyl-c-butyl, 1-n-propyl-c-propyl, 2-n-propyl-c-propyl, 1-i-propyl-c-propyl, 2-i-propyl-c-propyl, 1,2,2-trimethyl-c-propyl, 1,2,3-trimethyl-c-propyl, 2,2,3-trimethyl-c-propyl, 1-ethyl-2-methyl-c-propyl, 2-ethyl-1-methyl-c-propyl, 2-ethyl-2-methyl-c-propyl, 2-ethyl-3-methyl-c-propyl and the like may be mentioned.
A C1-10 alkyl group may be linear, branched or a C3-10 cycloalkyl group, and in addition to those mentioned above, 1-methyl-1-ethyl-n-pentyl, 1-heptyl, 2-heptyl, 1-ethyl-1,2-dimethyl-n-propyl, 1-ethyl-2,2-dimethyl-n-propyl, 1-octyl, 3-octyl, 4-methyl-3-n-heptyl, 6-methyl-2-n-heptyl, 2-propyl-1-n-heptyl, 2,4,4-trimethyl-1-n-pentyl, 1-nonyl, 2-nonyl, 2,6-dimethyl-4-n-heptyl, 3-ethyl-2,2-dimethyl-3-n-pentyl, 3,5,5-trimethyl-1-n-hexyl, 1-decyl, 2-decyl, 4-decyl, 3,7-dimethyl-1-n-octyl, 3,7-dimethyl-3-n-octyl, c-heptyl, c-octyl, 1-methyl-c-hexyl, 2-methyl-c-hexyl, 3-methyl-c-hexyl, 1,2-dimethyl-c-hexyl, 1-ethyl-c-hexyl, 1-methyl-c-pentyl, 2-methyl-c-pentyl, 3-methyl-c-pentyl and the like may be mentioned.
A C2-10 alkyl group may be linear, branched or a C3-10 cycloalkyl group, and those mentioned above as C1-10 alkyl groups except for a methyl group may be mentioned.
As a C2-6 alkynyl group, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 2-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 1-n-propyl-2-propynyl, 2-ethyl-3-butynyl, 1-methyl-1-ethyl-2-propynyl, 1-i-propyl-2-propynyl and the like may be mentioned.
A C2-10 alkynyl group may be linear or branched, and in addition to those mentioned above, 1-methyl-n-hexynyl, 1,2-dimethyl-n-hexynyl, 1-ethyl-n-hexynyl, 1-n-heptynyl, 2-n-heptynyl, 3-n-heptynyl, 4-n-heptynyl, 1-n-octynyl, 2-n-octynyl, 3-n-octynyl and the like may be mentioned.
A C2-6 alkenyl group may be linear, branched or a C3-6 cycloalkenyl group, and ethenyl, 1-propenyl, 2-propenyl, 1-methyl-1-ethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methyl-1-propenyl, 2-methyl-2-propenyl, 1-ethylethenyl, 1-methyl-1-propenyl, 1-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-n-propylethenyl, 1-methyl-1-butenyl, 1-methyl-2-butenyl, 1-methyl-3-butenyl, 2-ethyl-2-propenyl, 2-methyl-1-butenyl, 2-methyl-2-butenyl, 2-methyl-3-butenyl, 3-methyl-1-butenyl, 3-methyl-2-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1-i-propylethenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-c-pentenyl, 2-c-pentenyl, 3-c-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 1-methyl-2-pentenyl, 1-methyl-3-pentenyl, 1-methyl-4-pentenyl, 1-n-butylethenyl, 2-methyl-1-pentenyl, 2-methyl-2-pentenyl, 2-methyl-3-pentenyl, 2-methyl-4-pentenyl, 2-n-propyl-2-propenyl, 3-methyl-1-pentenyl, 3-methyl-2-pentenyl, 3-methyl-3-pentenyl, 3-methyl-4-pentenyl, 3-ethyl-3-butenyl, 4-methyl-1-pentenyl, 4-methyl-2-pentenyl, 4-methyl-3-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1-methyl-2-ethyl-2-propenyl, 1-s-butylethenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 1-i-butylethenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 2-i-propyl-2-propenyl, 3,3-dimethyl-1-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 1-n-propyl-1-propenyl, 1-n-propyl-2-propenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-t-butylethenyl, 1-methyl-1-ethyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl, 1-ethyl-2-methyl-2-propenyl, 1-i-propyl-1-propenyl, 1-i-propyl-2-propenyl, 1-methyl-2-c-pentenyl, 1-methyl-3-c-pentenyl, 2-methyl-1-c-pentenyl, 2-methyl-2-c-pentenyl, 2-methyl-3-c-pentenyl, 2-methyl-4-c-pentenyl, 2-methyl-5-c-pentenyl, 2-methylene-c-pentyl, 3-methyl-1-c-pentenyl, 3-methyl-2-c-pentenyl, 3-methyl-3-c-pentenyl, 3-methyl-4-c-pentenyl, 3-methyl-5-c-pentenyl, 3-methylene-c-pentyl, 1-c-hexenyl, 2-c-hexenyl, 3-c-hexenyl and the like may be mentioned.
A C2-10 alkenyl group may be linear, branched or a C3-10 cycloalkenyl group, and in addition to those mentioned above, 1-methyl-n-hexenyl, 1,2-dimethyl-n-hexenyl, 1-ethyl-n-hexenyl, 1-n-heptenyl, 2-n-heptenyl, 3-n-heptenyl, 4-n-heptenyl, 1-n-octenyl, 2-n-octenyl, 3-n-octenyl, 1-methyl-c-hexenyl, 1,2-dimethyl-c-hexenyl, 1-ethyl-c-hexenyl, 1-c-heptenyl, 2-c-heptenyl, 3-c-heptenyl, 4-c-heptenyl, 1-c-octenyl, 2-c-octenyl, 3-c-octenyl, 4-c-octenyl and the like may be mentioned.
A C2-9 heterocyclic group may be a heteromonocyclic or fused heterobicyclic group consisting of at least one atom optionally selected from nitrogen atoms, oxygen atoms and sulfur atoms and from 2 to 9 carbon atoms, and specifically, the following structures may be mentioned.
A C2-14 aryl group may be a C6-14 aryl group containing no hetero atoms as ring constituting atoms or a C2-9 aromatic heterocyclic group, and a C2-6 aromatic heterocyclic group may be a 5 to 7-membered C2-6 heteromonocyclic group or 8 to 10-membered C5-9 fused heterobicyclic group containing from 1 to 3 oxygen atoms, nitrogen atoms or sulfur atoms singly or in combination.
As a C6-14 aryl group containing no hetero atoms, a phenyl group, a 1-indenyl group, a 2-indenyl group, a 3-indenyl group, a 4-indenyl group, a 5-indenyl group, a 6-indenyl group, a 7-indenyl group, an α-naphthyl group, a β-naphthyl group, a 1-tetrahydronaphthyl group, a 2-tetrahydronaphthyl group, a 5-tetrahydronaphthyl group, a 6-tetrahydronaphthyl group, an o-biphenylyl group, a m-biphenylyl group, a p-biphenylyl group, a 1-anthryl group, a 2-anthryl group, a 9-anthryl group, a 1-phenanthryl group, a 2-phenanthryl group, a 3-phenanthryl group, a 4-phenanthryl group, a 9-phenanthryl group or the like may be mentioned.
A 5 to 7-membered C2-6 heteromonocyclic group may be a 2-thienyl group, a 3-thienyl group, a 2-furyl group, a 3-furyl group, a 2-pyranyl group, a 3-pyranyl group, a 4-pyranyl group, a 1-pyrrolyl group, a 2-pyrrolyl group, a 3-pyrrolyl group, a 1-imidazolyl group, a 2-imidazolyl group, a 4-imidazolyl group, a 1-pyrazolyl group, a 3-pyrazolyl group, a 4-pyrazolyl group, a 2-thiazolyl group, a 4-thiazolyl group, a 5-thiazolyl group, a 3-isothiazolyl group, a 4-isothiazolyl group, a 5-isothiazolyl group, a 2-oxazolyl group, a 4-oxazolyl group, a 5-oxazolyl group, a 3-isoxazolyl group, a 4-isoxazolyl group, a 5-isoxazolyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 2-pyrazinyl group, a 2-pyrimidinyl group, a 4-pyrimidinyl group, a 5-pyrimidinyl group, a 3-pyridazinyl group, a 4-pyridazinyl group, a 2-1,3,4-oxadiazolyl group, a 2-1,3,4-thiadiazolyl group, a 3-1,2,4-oxadiazolyl group, a 5-1,2,4-oxadiazolyl group, a 3-1,2,4-thiadiazolyl group, a 5-1,2,4-thiadiazolyl group, a 3-1,2,5-oxadiazolyl group, a 3-1,2,5-thiadiazolyl group or the like.
A 8 to 10-membered C5-9 fused heterocyclic group may be a 2-benzofuranyl group, a 3-benzofuranyl group, a 4-benzofuranyl group, a 5-benzofuranyl group, a 6-benzofuranyl group, a 7-benzofuranyl group, a 1-isobenzofuranyl group, a 4-isobenzofuranyl group, a 5-isobenzofuranyl group, a 2-benzothienyl group, a 3-benzothienyl group, a 4-benzothienyl group, a 5-benzothienyl group, a 6-benzothienyl group, a 7-benzothienyl group, a 1-isobenzothienyl group, a 4-isobenzothienyl group, a 5-isobenzothienyl group, a 2-chromenyl group, a 3-chromenyl group, a 4-chromenyl group, a 5-chromenyl group, a 6-chromenyl group, a 7-chromenyl group, a 8-chromenyl group, a 1-indolizinyl group, a 2-indolizinyl group, a 3-indolizinyl group, a 5-indolizinyl group, a 6-indolizinyl group, a 7-indolizinyl group, a 8-indolizinyl group, a 1-isoindolyl group, a 2-isoindolyl group, a 4-isoindolyl group, a 5-isoindolyl group, a 1-indolyl group, a 2-indolyl group, a 3-indolyl group, a 4-indolyl group, a 5-indolyl group, a 6-indolyl group, a 7-indolyl group, 1-indazolyl group, a 2-indazolyl group, a 3-indazolyl group, a 4-indazolyl group, a 5-indazolyl group, a 6-indazolyl group, a 7-indazolyl group, a 1-purinyl group, a 2-purinyl group, a 3-purinyl group, a 6-purinyl group, a 7-purinyl group, a 8-purinyl group, a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 5-quinolyl group, a 6-quinolyl group, a 7-quinolyl group, a 8-quinolyl group, a 1-isoquinolyl group, a 3-isoquinolyl group, a 4-isoquinolyl group, a 5-isoquinolyl group, a 6-isoquinolyl group, a 7-isoquinolyl group, a 8-isoquinolyl group, a 1-phthalazinyl group, a 5-phthalazinyl group, a 6-phthalazinyl group, a 1-2,7-naphthyridinyl group, a 3-2,7-naphthyridinyl group, a 4-2,7-naphthyridinyl group, a 1-2,6-naphthyridinyl group, a 3-2,6-naphthyridinyl group, a 4-2,6-naphthyridinyl group, a 2-1,8-naphthyridinyl group, a 3-1,8-naphthyridinyl group, a 4-1,8-naphthyridinyl group, a 2-1,7-naphthyridinyl group, a 3-1,7-naphthyridinyl group, a 4-1,7-naphthyridinyl group, a 5-1,7-naphthyridinyl group, a 6-1,7-naphthyridinyl group, a 8-1,7-naphthyridinyl group, 2-1,6-naphthyridinyl group, a 3-1,6-naphthyridinyl group, a 4-1,6-naphthyridinyl group, a 5-1,6-naphthyridinyl group, a 7-1,6-naphthyridinyl group, a 8-1,6-naphthyridinyl group, a 2-1,5-naphthyridinyl group, a 3-1,5-naphthyridinyl group, a 4-1,5-naphthyridinyl group, a 6-1,5-naphthyridinyl group, a 7-1,5-naphthyridinyl group, a 8-1,5-naphthyridinyl group, a 2-quinoxalinyl group, a 5-quinoxalinyl group, a 6-quinoxalinyl group, a 2-quinazolinyl group, a 4-quinazolinyl group, a 5-quinazolinyl group, a 6-quinazolinyl group, a 7-quinazolinyl group, a 8-quinazolinyl group, a 3-cinnolinyl group, a 4-cinnolinyl group, a 5-cinnolinyl group, a 6-cinnolinyl group, a 7-cinnolinyl group, a 8-cinnolinyl group, a 2-pterdinyl group, a 4-pterdinyl group, a 6-pterdinyl group, a 7-pterdinyl group or the like.
A C2-14 aryloxy group may be a C6-14 aryloxy group containing no hetero atoms as ring constituting atoms or a C2-9 aromatic heterocyclic oxy group, and a C2-9 aromatic heterocyclic oxy group may be a 5 to 7-membered C2-6 heteromonocyclic oxy group or 8 to 10-membered C5-9 fused heterobicyclic oxy group containing from 1 to 3 oxygen atoms, nitrogen atoms or sulfur atoms singly or in combination.
As a C6-14 aryloxy group containing no hetero atoms, a phenyloxy group, a 1-indenyloxy group, a 2-indenyloxy group, a 3-indenyloxy group, a 4-indenyloxy group, a 5-indenyloxy group, a 6-indenyloxy group, a 7-indenyloxy group, an α-naphthyloxy group, a β-naphthyloxy group, a 1-tetrahydronaphthyloxy group, a 2-tetrahydronaphthyloxy group, a 5-tetrahydronaphthyloxy group, a 6-tetrahydronaphthyloxy group, an o-biphenylyloxy group, a m-biphenylyloxy group, a p-biphenylyloxy group, a 1-anthryloxy group, a 2-anthryloxy group, a 9-anthryloxy group, a 1-phenanthryloxy group, a 2-phenanthryloxy group, a 3-phenanthryloxy group, a 4-phenanthryloxy group, a 9-phenanthryloxy group or the like may be mentioned.
A 5 to 7-membered C2-6 heteromonocyclic oxy group may be a 2-thienyloxy group, a 3-thienyloxy group, a 2-furyloxy group, a 3-furyloxy group, a 2-pyranyloxy group, a 3-pyranyloxy group, a 4-pyranyloxy group, a 1-pyrrolyloxy group, a 2-pyrrolyloxy group, a 3-pyrrolyloxy group, a 1-imidazolyloxy group, a 2-imidazolyloxy group, a 4-imidazolyloxy group, a 1-pyrazolyloxy group, a 3-pyrazolyloxy group, a 4-pyrazolyloxy group, a 2-thiazolyloxy group, a 4-thiazolyloxy group, a 5-thiazolyloxy group, a 3-isothiazolyloxy group, a 4-isothiazolyloxy group, a 5-isothiazolyloxy group, a 2-oxazolyloxy group, a 4-oxazolyloxy group, a 5-oxazolyloxy group, a 3-isoxazolyloxy group, a 4-isoxazolyloxy group, a 5-isoxazolyloxy group, a 2-pyridyloxy group, a 3-pyridyloxy group, a 4-pyridyloxy group, a 2-pyrazinyloxy group, a 2-pyrimidinyloxy group, a 4-pyrimidinyloxy group, a 5-pyrimidinyloxy group, a 3-pyridazinyloxy group, a 4-pyridazinyloxy group, a 2-1,3,4-oxadiazolyloxy group, a 2-1,3,4-thiadiazolyloxy group, a 3-1,2,4-oxadiazolyloxy group, a 5-1,2,4-oxadiazolyloxy group, a 3-1,2,4-thiadiazolyloxy group, a 5-1,2,4-thiadiazolyloxy group, a 3-1,2,5-oxadiazolyloxy group, a 3-1,2,5-thiadiazolyloxy group or the like.
A 8 to 10-membered C5-9 fused heterobicyclic oxy group may be a 2-benzofuranyloxy group, a 3-benzofuranyloxy group, a 4-benzofuranyloxy group, a 5-benzofuranyloxy group, a 6-benzofuranyloxy group, a 7-benzofuranyloxy group, a 1-isobenzofuranyloxy group, a 4-isobenzofuranyloxy group, a 5-isobenzofuranyloxy group, a 2-benzothienyloxy group, a 3-benzothienyloxy group, a 4-benzothienyloxy group, a 5-benzothienyloxy group, a 6-benzothienyloxy group, a 7-benzothienyloxy group, a 1-isobenzothienyloxy group, a 4-isobenzothienyloxy group, a 5-isobenzothienyloxy group, a 2-chromenyloxy group, a 3-chromenyloxy group, a 4-chromenyloxy group, a 5-chromenyloxy group, a 6-chromenyloxy group, a 7-chromenyloxy group, a 8-chromenyloxy group, a 1-indolizinyloxy group, a 2-indolizinyloxy group, a 3-indolizinyloxy group, a 5-indolizinyloxy group, a 6-indolizinyloxy group, a 7-indolizinyloxy group, a 8-indolizinyloxy group, a 1-isoindolyloxy group, a 2-isoindolyloxy group, a 4-isoindolyloxy group, a 5-isoindolyloxy group, a 1-indolyloxy group, a 2-indolyloxy group, a 3-indolyloxy group, a 4-indolyloxy group, a 5-indolyloxy group, a 6-indolyloxy group, a 7-indolyloxy group, 1-indazolyloxy group, a 2-indazolyloxy group, a 3-indazolyloxy group, a 4-indazolyloxy group, a 5-indazolyloxy group, a 6-indazolyloxy group, a 7-indazolyloxy group, a 1-purinyloxy group, a 2-purinyloxy group, a 3-purinyloxy group, a 6-purinyloxy group, a 7-purinyloxy group, a 8-purinyloxy group, a 2-quinolyloxy group, a 3-quinolyloxy group, a 4-quinolyloxy group, a 5-quinolyloxy group, a 6-quinolyloxy group, a 7-quinolyloxy group, a 8-quinolyloxy group, a 1-isoquinolyloxy group, a 3-isoquinolyloxy group, a 4-isoquinolyloxy group, a 5-isoquinolyloxy group, a 6-isoquinolyloxy group, a 7-isoquinolyloxy group, a 8-isoquinolyloxy group, a 1-phthalazinyloxy group, a 5-phthalazinyloxy group, a 6-phthalazinyloxy group, a 1-2,7-naphthyridinyloxy group, a 3-2,7-naphthyridinyloxy group, a 4-2,7-naphthyridinyloxy group, a 1-2,6-naphthyridinyloxy group, a 3-2,6-naphthyridinyloxy group, a 4-2,6-naphthyridinyloxy group, a 2-1,8-naphthyridinyloxy group, a 3-1,8-naphthyridinyloxy group, a 4-1,8-naphthyridinyloxy group, a 2-1,7-naphthyridinyloxy group, a 3-1,7-naphthyridinyloxy group, a 4-1,7-naphthyridinyloxy group, a 5-1,7-naphthyridinyloxy group, a 6-1,7-naphthyridinyloxy group, a 8-1,7-naphthyridinyloxy group, 2-1,6-naphthyridinyloxy group, a 3-1,6-naphthyridinyloxy group, a 4-1,6-naphthyridinyloxy group, a 5-1,6-naphthyridinyloxy group, a 7-1,6-naphthyridinyloxy group, a 8-1,6-naphthyridinyloxy group, a 2-1,5-naphthyridinyloxy group, a 3-1,5-naphthyridinyloxy group, a 4-1,5-naphthyridinyloxy group, a 6-1,5-naphthyridinyloxy group, a 7-1,5-naphthyridinyloxy group, a 8-1,5-naphthyridinyloxy group, a 2-quinoxalinyloxy group, a 5-quinoxalinyloxy group, a 6-quinoxalinyloxy group, a 2-quinazolinyloxy group, a 4-quinazolinyloxy group, a 5-quinazolinyloxy group, a 6-quinazolinyloxy group, a 7-quinazolinyloxy group, a 8-quinazolinyloxy group, a 3-cinnolinyloxy group, a 4-cinnolinyloxy group, a 5-cinnolinyloxy group, a 6-cinnolinyloxy group, a 7-cinnolinyloxy group, a 8-cinnolinyloxy group, a 2-pterdinyloxy group, a 4-pterdinyloxy group, a 6-pterdinyloxy group, a 7-pterdinyloxy group or the like.
A C1-6 alkylcarbonyl group may linear, branched or a C3-6 cycloalkylcarbonyl group, and be methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, i-propylcarbonyl, c-propylcarbonyl, n-butylcarbonyl, i-butylcarbonyl, s-butylcarbonyl, t-butylcarbonyl, c-butylcarbonyl, 1-methyl-c-propylcarbonyl, 2-methyl-c-propylcarbonyl, n-pentylcarbonyl, 1-methyl-n-butylcarbonyl, 2-methyl-n-butylcarbonyl, 3-methyl-n-butylcarbonyl, 1,1-dimethyl-n-propylcarbonyl, 1,2-dimethyl-n-propylcarbonyl, 2,2-dimethyl-n-propylcarbonyl, 1-ethyl-n-propylcarbonyl, c-pentylcarbonyl, 1-methyl-c-butylcarbonyl, 2-methyl-c-butylcarbonyl, 3-methyl-c-butylcarbonyl, 1,2-dimethyl-c-propylcarbonyl, 2,3-dimethyl-c-propylcarbonyl, 1-ethyl-c-propylcarbonyl, 2-ethyl-c-propylcarbonyl, n-hexylcarbonyl, 1-methyl-n-pentylcarbonyl, 2-methyl-n-pentylcarbonyl, 3-methyl-n-pentylcarbonyl, 4-methyl-n-pentylcarbonyl, 1,1-dimethyl-n-butylcarbonyl, 1,2-dimethyl-n-butylcarbonyl, 1,3-dimethyl-n-butylcarbonyl, 2,2-dimethyl-n-butylcarbonyl, 2,3-dimethyl-n-butylcarbonyl, 3,3-dimethyl-n-butylcarbonyl, 1-ethyl-n-butylcarbonyl, 2-ethyl-n-butylcarbonyl, 1,1,2-trimethyl-n-propylcarbonyl, 1,2,2-trimethyl-n-propylcarbonyl, 1-ethyl-1-methyl-n-propylcarbonyl, 1-ethyl-2-methyl-n-propylcarbonyl, c-hexylcarbonyl, 1-methyl-c-pentylcarbonyl, 2-methyl-c-pentylcarbonyl, 3-methyl-c-pentylcarbonyl, 1-ethyl-c-butylcarbonyl, 2-ethyl-c-butylcarbonyl, 3-ethyl-c-butylcarbonyl, 1,2-dimethyl-c-butylcarbonyl, 1,3-dimethyl-c-butylcarbonyl, 2,2-dimethyl-c-butylcarbonyl, 2,3-dimethyl-c-butylcarbonyl, 2,4-dimethyl-c-butylcarbonyl, 3,3-dimethyl-c-butylcarbonyl, 1-n-propyl-c-propylcarbonyl, 2-n-propyl-c-propylcarbonyl, 1-i-propyl-c-propylcarbonyl, 2-i-propyl-c-propylcarbonyl, 1,2,2-trimethyl-c-propylcarbonyl, 1,2,3-trimethyl-c-propylcarbonyl, 2,2,3-trimethyl-c-propylcarbonyl, 1-ethyl-2-methyl-c-propylcarbonyl, 2-ethyl-1-methyl-c-propylcarbonyl, 2-ethyl-2-methyl-c-propylcarbonyl, 2-ethyl-3-methyl-c-propylcarbonyl or the like may be mentioned.
A C1-10 alkylcarbonyl may be linear, branched or a C3-10 cycloalkylcarbonyl group, and in addition to those mentioned above, 1-methyl-1-ethyl-n-pentylcarbonyl, 1-heptylcarbonyl, 2-heptylcarbonyl, 1-ethyl-1,2-dimethyl-n-propylcarbonyl, 1-ethyl-2,2-dimethyl-n-propylcarbonyl, 1-octylcarbonyl, 3-octylcarbonyl, 4-methyl-3-n-heptylcarbonyl, 6-methyl-2-n-heptylcarbonyl, 2-propyl-1-n-heptylcarbonyl, 2,4,4-trimethyl-1-n-pentylcarbonyl, 1-nonylcarbonyl, 2-nonylcarbonyl, 2,6-dimethyl-4-n-heptylcarbonyl, 3-ethyl-2,2-dimethyl-3-n-pentylcarbonyl, 3,5,5-trimethyl-1-n-hexylcarbonyl, 1-decylcarbonyl, 2-decylcarbonyl, 4-decylcarbonyl, 3,7-dimethyl-1-n-octylcarbonyl, 3,7-dimethyl-3-n-octylcarbonyl or the like may be mentioned.
A C1-6 alkylaminosulfonyl group may be linear, branched or a C3-6 cycloalkylaminosulfonyl group, and methylaminosulfonyl, ethylaminosulfonyl, n-propylaminosulfonyl, i-propylaminosulfonyl, c-propylaminosulfonyl, n-butylaminosulfonyl, i-butylaminosulfonyl, s-butylaminosulfonyl, t-butylaminosulfonyl, c-butylaminosulfonyl, 1-methyl-c-propylaminosulfonyl, 2-methyl-c-propylaminosulfonyl, n-pentylaminosulfonyl, 1-methyl-n-butylaminosulfonyl, 2-methyl-n-butylaminosulfonyl, 3-methyl-n-butylaminosulfonyl, 1,1-dimethyl-n-propylaminosulfonyl, 1,2-dimethyln-propylaminosulfonyl, 2,2-dimethyln-propylaminosulfonyl, 1-ethyl-n-propylaminosulfonyl, c-pentylaminosulfonyl, 1-methyl-c-butylaminosulfonyl, 2-methyl-c-butylaminosulfonyl, 3-methyl-c-butylaminosulfonyl, 1,2-dimethyl-c-propylaminosulfonyl, 2,3-dimethyl-c-propylaminosulfonyl, 1-ethyl-c-propylaminosulfonyl, 2-ethyl-c-propylaminosulfonyl, n-hexylaminosulfonyl, 1-methyl-n-pentylaminosulfonyl, 2-methyl-n-pentylaminosulfonyl, 3-methyl-n-pentylaminosulfonyl, 4-methyl-n-pentylaminosulfonyl, 1,1-dimethyl-n-butylaminosulfonyl, 1,2-dimethyl-n-butylaminosulfonyl, 1,3-dimethyl-n-butylaminosulfonyl, 2,2-dimethyl-n-butylaminosulfonyl, 2,3-dimethyl-n-butylaminosulfonyl, 3,3-dimethyl-n-butylaminosulfonyl, 1-ethyl-n-butylaminosulfonyl, 2-ethyl-n-butylaminosulfonyl, 1,1,2-trimethyl-n-propylaminosulfonyl, 1,2,2-trimethyl-n-propylaminosulfonyl, 1-ethyl-1-methyl-n-propylaminosulfonyl, 1-ethyl-2-methyl-n-propylaminosulfonyl, c-hexylaminosulfonyl, 1-methyl-c-pentylaminosulfonyl, 2-methyl-c-pentylaminosulfonyl, 3-methyl-c-pentylaminosulfonyl, 1-ethyl-c-butylaminosulfonyl, 2-ethyl-c-butylaminosulfonyl, 3-ethyl-c-butylaminosulfonyl, 1,2-dimethyl-c-butylaminosulfonyl, 1,3-dimethyl-c-butylaminosulfonyl, 2,2-dimethyl-c-butylaminosulfonyl, 2,3-dimethyl-c-butylaminosulfonyl, 2,4-dimethyl-c-butylaminosulfonyl, 3,3-dimethyl-c-butylaminosulfonyl, 1-n-propyl-c-propylaminosulfonyl, 2-n-propyl-c-propylaminosulfonyl, 1-i-propyl-c-propylaminosulfonyl, 2-i-propyl-c-propylaminosulfonyl, 1,2,2-trimethyl-c-propylaminosulfonyl, 1,2,3-trimethyl-c-propylaminosulfonyl, 2,2,3-trimethyl-c-propylaminosulfonyl, 1-ethyl-2-methyl-c-propylaminosulfonyl, 2-ethyl-1-methyl-c-propylaminosulfonyl, 2-ethyl-2-methyl-c-propylaminosulfonyl, 2-ethyl-3-methyl-c-propylaminosulfonyl or the like may be mentioned.
A C1-10 alkylaminosulfonyl group may be linear, branched or a C3-10 cycloalkylsulfonylamino group, and in addition to those mentioned above, 1-methyl-1-ethyl-n-pentylaminosulfonyl, 1-heptylaminosulfonyl, 2-heptylaminosulfonyl, 1-ethyl-1,2-dimethyl-n-propylaminosulfonyl, 1-ethyl-2,2-dimethyl-n-propylaminosulfonyl, 1-octylaminosulfonyl, 3-octylaminosulfonyl, 4-methyl-3-n-heptylaminosulfonyl, 6-methyl-2-n-heptylaminosulfonyl, 2-propyl-1-n-heptylaminosulfonyl, 2,4,4-trimethyl-1-n-pentylaminosulfonyl, 1-nonylaminosulfonyl, 2-nonylaminosulfonyl, 2,6-dimethyl-4-n-heptylaminosulfonyl, 3-ethyl-2,2-dimethyl-3-n-pentylaminosulfonyl, 3,5,5-trimethyl-1-n-hexylaminosulfonyl, 1-decylaminosulfonyl, 2-decylaminosulfonyl, 4-decylaminosulfonyl, 3,7-dimethyl-1-n-octylaminosulfonyl, 3,7-dimethyl-3-n-octylaminosulfonyl, c-heptylaminosulfonyl, c-octylaminosulfonyl, 1-methyl-c-hexylaminosulfonyl, 2-methyl-c-hexylaminosulfonyl, 3-methyl-c-hexylaminosulfonyl, 1,2-dimethyl-c-hexylaminosulfonyl, 1-ethyl-c-hexylaminosulfonyl, 1-methyl-c-pentylaminosulfonyl, 2-methyl-c-pentylaminosulfonyl, 3-methyl-c-pentylaminosulfonyl or the like may be mentioned.
A C1-6 alkylsulfonyl group may be linear, branched or a C3-6 cycloalkylsulfonyl group, and methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, i-propylsulfonyl, c-propylsulfonyl, n-butylsulfonyl, i-butylsulfonyl, s-butylsulfonyl, t-butylsulfonyl, c-butylsulfonyl, 1-methyl-c-propylsulfonyl, 2-methyl-c-propylsulfonyl, n-pentylsulfonyl, 1-methyl-n-butylsulfonyl, 2-methyl-n-butylsulfonyl, 3-methyl-n-butylsulfonyl, 1,1-dimethyl-n-propylsulfonyl, 1,2-dimethyl-n-propylsulfonyl, 2,2-dimethyl-n-propylsulfonyl, 1-ethyl-n-propylsulfonyl, c-pentylsulfonyl, 1-methyl-c-butylsulfonyl, 2-methyl-c-butylsulfonyl, 3-methyl-c-butylsulfonyl, 1,2-dimethyl-c-propylsulfonyl, 2,3-dimethyl-c-propylsulfonyl, 1-ethyl-c-propylsulfonyl, 2-ethyl-c-propylsulfonyl, n-hexylsulfonyl, 1-methyl-n-pentylsulfonyl, 2-methyl-n-pentylsulfonyl, 3-methyl-n-pentylsulfonyl, 4-methyl-n-pentylsulfonyl, 1,1-dimethyl-n-butylsulfonyl, 1,2-dimethyl-n-butylsulfonyl, 1,3-dimethyl-n-butylsulfonyl, 2,2-dimethyl-n-butylsulfonyl, 2,3-dimethyl-n-butylsulfonyl, 3,3-dimethyl-n-butylsulfonyl, 1-ethyl-n-butylsulfonyl, 2-ethyl-n-butylsulfonyl, 1,1,2-trimethyl-n-propylsulfonyl, 1,2,2-trimethyl-n-propylsulfonyl, 1-ethyl-1-methyl-n-propylsulfonyl, 1-ethyl-2-methyl-n-propylsulfonyl, c-hexylsulfonyl, 1-methyl-c-pentylsulfonyl, 2-methyl-c-pentylsulfonyl, 3-methyl-c-pentylsulfonyl, 1-ethyl-c-butylsulfonyl, 2-ethyl-c-butylsulfonyl, 3-ethyl-c-butylsulfonyl, 1,2-dimethyl-c-butylsulfonyl, 1,3-dimethyl-c-butylsulfonyl, 2,2-dimethyl-c-butylsulfonyl, 2,3-dimethyl-c-butylsulfonyl, 2,4-dimethyl-c-butylsulfonyl, 3,3-dimethyl-c-butylsulfonyl, 1-n-propyl-c-propylsulfonyl, 2-n-propyl-c-propylsulfonyl, 1-i-propyl-c-propylsulfonyl, 2-i-propyl-c-propylsulfonyl, 1,2,2-trimethyl-c-propylsulfonyl, 1,2,3-trimethyl-c-propylsulfonyl, 2,2,3-trimethyl-c-propylsulfonyl, 1-ethyl-2-methyl-c-propylsulfonyl, 2-ethyl-1-methyl-c-propylsulfonyl, 2-ethyl-2-methyl-c-propylsulfonyl, 2-ethyl-3-methyl-c-propylsulfonyl or the like may be mentioned.
A C1-10 alkylsulfonyl group may be linear, branched or a C3-10 cycloalkylsulfonyl group, and in addition to those mentioned above, 1-methyl-1-ethyl-n-pentylsulfonyl, 1-heptylsulfonyl, 2-heptylsulfonyl, 1-ethyl-1,2-dimethyl-n-propylsulfonyl, 1-ethyl-2,2-dimethyl-n-propylsulfonyl, 1-octylsulfonyl, 3-octylsulfonyl, 4-methyl-3-n-heptylsulfonyl, 6-methyl-2-n-heptylsulfonyl, 2-propyl-1-n-n-heptylsulfonyl, 2,4,4-trimethyl-1-n-pentylsulfonyl, 1-nonylsulfonyl, 2-nonylsulfonyl, 2,6-dimethyl-4-n-heptylsulfonyl, 3-ethyl-2,2-dimethyl-3-n-pentylsulfonyl, 3,5,5-trimethyl-1-n-hexylsulfonyl, 1-decylsulfonyl, 2-decylsulfonyl, 4-decylsulfonyl, 3,7-dimethyl-1-n-octylsulfonyl, 3,7-dimethyl-3-n-octylsulfonyl, c-heptylsulfonyl, c-octylsulfonyl, 1-methyl-c-hexylsulfonyl, 2-methyl-c-hexylsulfonyl, 3-methyl-c-hexylsulfonyl, 1,2-dimethyl-c-hexylsulfonyl, 1-ethyl-c-hexylsulfonyl, 1-methyl-c-pentylsulfonyl, 2-methyl-c-pentylsulfonyl, 3-methyl-c-pentylsulfonyl or the like may be mentioned.
A C1-10 alkoxy group may be linear, branched or a C3-10 cycloalkoxy group, and methoxy, ethoxy, n-propoxy, i-propoxy, c-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, c-butoxy, 1-methyl-c-propoxy, 2-methyl-c-propoxy, n-pentyloxy, 1-methyl-n-butoxy, 2-methyl-n-butoxy, 3-methyl-n-butoxy, 1,1-dimethyl-n-propoxy, 1,2-dimethyl-n-propoxy, 2,2-dimethyl-n-propoxy, 1-ethyl-n-propoxy, c-pentyloxy, 1-methyl-c-butoxy, 2-methyl-c-butoxy, 3-methyl-c-butoxy, 1,2-dimethyl-c-propoxy, 2,3-dimethyl-c-propoxy, 1-ethyl-c-propoxy, 2-ethyl-c-propoxy, n-hexyloxy, 1-methyl-n-pentyloxy, 2-methyl-n-pentyloxy, 3-methyl-n-pentyloxy, 4-methyl-n-pentyloxy, 1,1-dimethyl-n-butoxy, 1,2-dimethyl-n-butoxy, 1,3-dimethyl-n-butoxy, 2,2-dimethyl-n-butoxy, 2,3-dimethyl-n-butoxy, 3,3-dimethyl-n-butoxy, 1-ethyl-n-butoxy, 2-ethyl-n-butoxy, 1,1,2-trimethyl-n-propoxy, 1,2,2-trimethyl-n-propoxy, 1-ethyl-1-methyl-n-propoxy, 1-ethyl-2-methyl-n-propoxy, c-hexyloxy, 1-methyl-c-pentyloxy, 2-methyl-c-pentyloxy, 3-methyl-c-pentyloxy, 1-ethyl-c-butoxy, 2-ethyl-c-butoxy, 3-ethyl-c-butoxy, 1,2-dimethyl-c-butoxy, 1,3-dimethyl-c-butoxy, 2,2-dimethyl-c-butoxy, 2,3-dimethyl-c-butoxy, 2,4-dimethyl-c-butoxy, 3,3-dimethyl-c-butoxy, 1-n-propyl-c-propoxy, 2-n-propyl-c-propoxy, 1-i-propyl-c-propoxy, 2-i-propyl-c-propoxy, 1,2,2-trimethyl-c-propoxy, 1,2,3-trimethyl-c-propoxy, 2,2,3-trimethyl-c-propoxy, 1-ethyl-2-methyl-c-propoxy, 2-ethyl-1-methyl-c-propoxy, 2-ethyl-2-methyl-c-propoxy, 2-ethyl-3-methyl-c-propoxy, 1-methyl-1-ethyl-n-pentyloxy, 1-heptyloxy, 2-heptyloxy, 1-ethyl-1,2-dimethyl-n-propyloxy, 1-ethyl-2,2-dimethyl-n-propyloxy, 1-octyloxy, 3-octyloxy, 4-methyl-3-n-heptyloxy, 6-methyl-2-n-heptyloxy, 2-propyl-1-n-heptyloxy, 2,4,4-trimethyl-1-n-pentyloxy, 1-nonyloxy, 2-nonyloxy, 2,6-dimethyl-4-n-heptyloxy, 3-ethyl-2,2-dimethyl-3-n-pentyloxy, 3,5,5-trimethyl-1-n-hexyloxy, 1-decyloxy, 2-decyloxy, 4-decyloxy, 3,7-dimethyl-1-n-octyloxy, 3,7-dimethyl-3-n-octyloxy or the like may be mentioned.
A C1-10 thioalkyl group may linear, branched or a C3-10 cyclothioalkyl group, and be methylthio, ethylthio, n-propylthio, i-propylthio, c-propylthio, n-butylthio, i-butylthio, s-butylthio, t-butylthio, c-butylthio, 1-methyl-c-propylthio, 2-methyl-c-propylthio, n-pentylthio, 1-methyl-n-butylthio, 2-methyl-n-butylthio, 3-methyl-n-butylthio, 1,1-dimethyl-n-propylthio, 1,2-dimethyl-n-propylthio, 2,2-dimethyl-n-propylthio, 1-ethyl-n-propylthio, c-pentylthio, 1-methyl-c-butylthio, 2-methyl-c-butylthio, 3-methyl-c-butylthio, 1,2-dimethyl-c-propylthio, 2,3-dimethyl-c-propylthio, 1-ethyl-c-propylthio, 2-ethyl-c-propylthio, n-hexylthio, 1-methyl-n-pentylthio, 2-methyl-n-pentylthio, 3-methyl-n-pentylthio, 4-methyl-n-pentylthio, 1,1-dimethyl-n-butylthio, 1,2-dimethyl-n-butylthio, 1,3-dimethyl-n-butylthio, 2,2-dimethyl-n-butylthio, 2,3-dimethyl-n-butylthio, 3,3-dimethyl-n-butylthio, 1-ethyl-n-butylthio, 2-ethyl-n-butylthio, 1,1,2-trimethyl-n-propylthio, 1,2,2-trimethyl-n-propylthio, 1-ethyl-1-methyl-n-propylthio, 1-ethyl-2-methyl-n-propylthio, c-hexylthio, 1-methyl-c-pentylthio, 2-methyl-c-pentylthio, 3-methyl-c-pentylthio, 1-ethyl-c-butylthio, 2-ethyl-c-butylthio, 3-ethyl-c-butylthio, 1,2-dimethyl-c-butylthio, 1,3-dimethyl-c-butylthio, 2,2-dimethyl-c-butylthio, 2,3-dimethyl-c-butylthio, 2,4-dimethyl-c-butylthio, 3,3-dimethyl-c-butylthio, 1-n-propyl-c-propylthio, 2-n-propyl-c-propylthio, 1-i-propyl-c-propylthio, 2-i-propyl-c-propylthio, 1,2,2-trimethyl-c-propylthio, 1,2,3-trimethyl-c-propylthio, 2,2,3-trimethyl-c-propylthio, 1-ethyl-2-methyl-c-propylthio, 2-ethyl-1-methyl-c-propylthio, 2-ethyl-2-methyl-c-propylthio, 2-ethyl-3-methyl-c-propylthio, 1-methyl-1-ethyl-n-pentyl thio, 1-heptylthio, 2-heptylthio, 1-ethyl-1,2-dimethyl-n-propylthio, 1-ethyl-2,2-dimethyl-n-propylthio, 1-octylthio, 3-octylthio, 4-methyl-3-n-heptylthio, 6-methyl-2-n-heptylthio, 2-propyl-1-n-heptylthio, 2,4,4-trimethyl-1-n-pentylthio, 1-nonylthio, 2-nonylthio, 2,6-dimethyl-4-n-heptylthio, 3-ethyl-2,2-dimethyl-3-n-pentylthio, 3,5,5-trimethyl-1-n-hexylthio, 1-decylthio, 2-decylthio, 4-decylthio, 3,7-dimethyl-1-n-octylthio, 3,7-dimethyl-3-n-octylthio or the like may be mentioned.
A C1-6 alkoxycarbonyl group may be linear, branched or a C3-6 cycloalkoxycarbonyl group, and methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, i-propoxycarbonyl, c-propoxycarbonyl, n-butoxycarbonyl, i-butoxycarbonyl, s-butoxycarbonyl, t-butoxycarbonyl, c-butoxycarbonyl, 1-methyl-c-propoxycarbonyl, 2-methyl-c-propoxycarbonyl, n-pentyloxycarbonyl, 1-methyl-n-butoxycarbonyl, 2-methyl-n-butoxycarbonyl, 3-methyl-n-butoxycarbonyl, 1,1-dimethyl-n-propoxycarbonyl, 1,2-dimethyl-n-propoxycarbonyl, 2,2-dimethyl-n-propoxycarbonyl, 1-ethyl-n-propoxycarbonyl, c-pentyloxycarbonyl, 1-methyl-c-butoxycarbonyl, 2-methyl-c-butoxycarbonyl, 3-methyl-c-butoxycarbonyl, 1,2-dimethyl-c-propoxycarbonyl, 2,3-dimethyl-c-propoxycarbonyl, 1-ethyl-c-propoxycarbonyl, 2-ethyl-c-propoxycarbonyl, n-hexyloxycarbonyl, 1-methyl-n-pentyloxycarbonyl, 2-methyl-n-pentyloxycarbonyl, 3-methyl-n-pentyloxycarbonyl, 4-methyl-n-pentyloxycarbonyl, 1,1-dimethyl-n-butoxycarbonyl, 1,2-dimethyl-n-butoxycarbonyl, 1,3-dimethyl-n-butoxycarbonyl, 2,2-dimethyl-n-butoxycarbonyl, 2,3-dimethyl-n-butoxycarbonyl, 3,3-dimethyl-n-butoxycarbonyl, 1-ethyl-n-butoxycarbonyl, 2-ethyl-n-butoxycarbonyl, 1,1,2-trimethyl-n-propoxycarbonyl, 1,2,2-trimethyl-n-propoxycarbonyl, 1-ethyl-1-methyl-n-propoxycarbonyl, 1-ethyl-2-methyl-n-propoxycarbonyl, c-hexyloxycarbonyl, 1-methyl-c-pentyloxycarbonyl, 2-methyl-c-pentyloxycarbonyl, 3-methyl-c-pentyloxycarbonyl, 1-ethyl-c-butoxycarbonyl, 2-ethyl-c-butoxycarbonyl, 3-ethyl-c-butoxycarbonyl, 1,2-dimethyl-c-butoxycarbonyl, 1,3-dimethyl-c-butoxycarbonyl, 2,2-dimethyl-c-butoxycarbonyl, 2,3-dimethyl-c-butoxycarbonyl, 2,4-dimethyl-c-butoxycarbonyl, 3,3-dimethyl-c-butoxycarbonyl, 1-n-propyl-c-propoxycarbonyl, 2-n-propyl-c-propoxycarbonyl, 1-i-propyl-c-propoxycarbonyl, 2-i-propyl-c-propoxycarbonyl, 1,2,2-trimethyl-c-propoxycarbonyl, 1,2,3-trimethyl-c-propoxycarbonyl, 2,2,3-trimethyl-c-propoxycarbonyl, 1-ethyl-2-methyl-c-propoxycarbonyl, 2-ethyl-1-methyl-c-propoxycarbonyl, 2-ethyl-2-methyl-c-propoxycarbonyl, 2-ethyl-3-methyl-c-propoxycarbonyl or the like may be mentioned.
A C1-10 alkoxycarbonyl group may be linear, branched or a C3-10 cycloalkoxycarbonyl group, and in addition to those mentioned above, 1-methyl-1-ethyl-n-pentyloxycarbonyl, 1-heptyloxycarbonyl, 2-heptyloxycarbonyl, 1-ethyl-1,2-dimethyl-n-propyloxycarbonyl, 1-ethyl-2,2-dimethyl-n-propyloxycarbonyl, 1-octyloxycarbonyl, 3-octyloxycarbonyl, 4-methyl-3-n-heptyloxycarbonyl, 6-methyl-2-n-heptyloxycarbonyl, 2-propyl-1-n-heptyloxycarbonyl, 2,4,4-trimethyl-1-n-pentyloxycarbonyl, 1-nonyloxycarbonyl, 2-nonyloxycarbonyl, 2,6-dimethyl-4-n-heptyloxycarbonyl, 3-ethyl-2,2-dimethyl-3-n-pentyloxycarbonyl, 3,5,5-trimethyl-1-n-hexyloxycarbonyl, 1-decyloxycarbonyl, 2-decyloxycarbonyl, 4-decyloxycarbonyl, 3,7-dimethyl-1-n-octyloxycarbonyl, 3,7-dimethyl-3-n-octyloxycarbonyl or the like may be mentioned.
A C1-10 alkylcarbonyloxy group may be linear, branched or a C3-10 cycloalkylcarbonyloxy group, and methylcarbonyloxy, ethylcarbonyloxy, n-propylcarbonyloxy, i-propylcarbonyloxy, c-propylcarbonyloxy, n-butylcarbonyloxy, i-butylcarbonyloxy, s-butylcarbonyloxy, t-butylcarbonyloxy, c-butylcarbonyloxy, 1-methyl-c-propylcarbonyloxy, 2-methyl-c-propylcarbonyloxy, n-pentylcarbonyloxy, 1-methyl-n-butylcarbonyloxy, 2-methyl-n-butylcarbonyloxy, 3-methyl-n-butylcarbonyloxy, 1,1-dimethyl-n-propylcarbonyloxy, 1,2-dimethyl-n-propylcarbonyloxy, 2,2-dimethyl-n-propylcarbonyloxy, 1-ethyl-n-propylcarbonyloxy, c-pentylcarbonyloxy, 1-methyl-c-butylcarbonyloxy, 2-methyl-c-butylcarbonyloxy, 3-methyl-c-butylcarbonyloxy, 1,2-dimethyl-c-propylcarbonyloxy, 2,3-dimethyl-c-propylcarbonyloxy, 1-ethyl-c-propylcarbonyloxy, 2-ethyl-c-propylcarbonyloxy, n-hexylcarbonyloxy, 1-methyl-n-pentylcarbonyloxy, 2-methyl-n-pentylcarbonyloxy, 3-methyl-n-pentylcarbonyloxy, 4-methyl-n-pentylcarbonyloxy, 1,1-dimethyl-n-butylcarbonyloxy, 1,2-dimethyl-n-butylcarbonyloxy, 1,3-dimethyl-n-butylcarbonyloxy, 2,2-dimethyl-n-butylcarbonyloxy, 2,3-dimethyl-n-butylcarbonyloxy, 3,3-dimethyl-n-butylcarbonyloxy, 1-ethyl-n-butylcarbonyloxy, 2-ethyl-n-butylcarbonyloxy, 1,1,2-trimethyl-n-propylcarbonyloxy, 1,2,2-trimethyl-n-propylcarbonyloxy, 1-ethyl-1-methyl-n-propylcarbonyloxy, 1-ethyl-2-methyl-n-propylcarbonyloxy, c-hexylcarbonyloxy, 1-methyl-c-pentylcarbonyloxy, 2-methyl-c-pentylcarbonyloxy, 3-methyl-c-pentylcarbonyloxy, 1-ethyl-c-butylcarbonyloxy, 2-ethyl-c-butylcarbonyloxy, 3-ethyl-c-butylcarbonyloxy, 1,2-dimethyl-c-butylcarbonyloxy, 1,3-dimethyl-c-butylcarbonyloxy, 2,2-dimethyl-c-butylcarbonyloxy, 2,3-dimethyl-c-butylcarbonyloxy, 2,4-dimethyl-c-butylcarbonyloxy, 3,3-dimethyl-c-butylcarbonyloxy, 1-n-propyl-c-propylcarbonyloxy, 2-n-propyl-c-propyl carbonyl oxy, 1-i-propyl-c-propylcarbonyloxy, 2-i-propyl-c-propylcarbonyloxy, 1,2,2-trimethyl-c-propylcarbonyloxy, 1,2,3-trimethyl-c-propylcarbonyloxy, 2,2,3-trimethyl-c-propylcarbonyloxy, 1-ethyl-2-methyl-c-propylcarbonyloxy, 2-ethyl-1-methyl-c-propylcarbonyloxy, 2-ethyl-2-methyl-c-propylcarbonyloxy, 2-ethyl-3-methyl-c-propylcarbonyloxy, 1-methyl-1-ethyl-n-pentylcarbonyloxy, 1-heptylcarbonyloxy, 2-heptylcarbonyloxy, 1-ethyl-1,2-dimethyl-n-propylcarbonyloxy, 1-ethyl-2,2-dimethyl-n-propylcarbonyloxy, 1-octyl carbonyl oxy, 3-octylcarbonyloxy, 4-methyl-3-n-heptylcarbonyloxy, 6-methyl-2-n-heptylcarbonyloxy, 2-propyl-1-n-heptylcarbonyloxy, 2,4,4-trimethyl-1-n-pentylcarbonyloxy, 1-nonylcarbonyloxy, 2-nonylcarbohyloxy, 2,6-dimethyl-4-n-heptylcarbonyloxy, 3-ethyl-2,2-dimethyl-3-n-pentylcarbonyloxy, 3,5,5-trimethyl-1-n-hexylcarbonyloxy, 1-decylcarbonyloxy, 2-decylcarbonyloxy, 4-decylcarbonyloxy, 3,7-dimethyl-1-n-octylcarbonyloxy, 3,7-dimethyl-3-n-octylcarbonyloxy or the like may be mentioned.
A C1-10 alkylcarbonylamino group may be linear, branched or a C3-10 cycloalkylcarbonylamino group, and methylcarbonylamino, ethylcarbonylamino, n-propylcarbonylamino, i-propylcarbonylamino, c-propylcarbonylamino, n-butylcarbonylamino, i-butylcarbonylamino, s-butylcarbonylamino, t-butylcarbonylamino, c-butylcarbonylamino, 1-methyl-c-propylcarbonylamino, 2-methyl-c-propylcarbonylamino, n-pentylcarbonylamino, 1-methyl-n-butylcarbonylamino, 2-methyl-n-butylcarbonylamino, 3-methyl-n-butylcarbonylamino, 1,1-dimethyl-n-propylcarbonylamino, 1,2-dimethyl-n-propylcarbonylamino, 2,2-dimethyl-n-propylcarbonylamino, 1-ethyl-n-propylcarbonylamino, c-pentylcarbonylamino, 1-methyl-c-butylcarbonylamino, 2-methyl-c-butylcarbonylamino, 3-methyl-c-butylcarbonylamino, 1,2-dimethyl-c-propylcarbonylamino, 2,3-dimethyl-c-propylcarbonylamino, 1-ethyl-c-propylcarbonylamino, 2-ethyl-c-propylcarbonylamino, n-hexylcarbonylamino, 1-methyl-n-pentylcarbonylamino, 2-methyl-n-pentylcarbonylamino, 3-methyl-n-pentylcarbonylamino, 4-methyl-n-pentylcarbonylamino, 1,1-dimethyl-n-butylcarbonylamino, 1,2-dimethyl-n-butylcarbonylamino, 1,3-dimethyl-n-butylcarbonylamino, 2,2-dimethyl-n-butylcarbonylamino, 2,3-dimethyl-n-butylcarbonylamino, 3,3-dimethyl-n-butylcarbonylamino, 1-ethyl-n-butylcarbonylamino, 2-ethyl-n-butylcarbonylamino, 1,1,2-trimethyl-n-propylcarbonylamino, 1,2,2-trimethyl-n-propylcarbonylamino, 1-ethyl-1-methyl-n-propylcarbonylamino, 1-ethyl-2-methyl-n-propylcarbonylamino, c-hexylcarbonylamino, 1-methyl-c-pentylcarbonylamino, 2-methyl-c-pentylcarbonylamino, 3-methyl-c-pentylcarbonylamino, 1-ethyl-c-butylcarbonylamino, 2-ethyl-c-butylcarbonylamino, 3-ethyl-c-butylcarbonylamino, 1,2-dimethyl-c-butylcarbonylamino, 1,3-dimethyl-c-butylcarbonylamino, 2,2-dimethyl-c-butylcarbonylamino, 2,3-dimethyl-c-butylcarbonylamino, 2,4-dimethyl-c-butylcarbonylamino, 3,3-dimethyl-c-butylcarbonylamino, 1-n-propyl-c-propylcarbonylamino, 2-n-propyl-c-propylcarbonylamino, 1-i-propyl-c-propylcarbonylamino, 2-i-propyl-c-propylcarbonylamino, 1,2,2-trimethyl-c-propyl-carbonylamino, 1,2,3-trimethyl-c-propylcarbonylamino, 2,2,3-trimethyl-c-propylcarbonylamino, 1-ethyl-2-methyl-c-propylcarbonylamino, 2-ethyl-1-methyl-c-propylcarbonylamino, 2-ethyl-2-methyl-c-propylcarbonylamino, 2-ethyl-3-methyl-c-propylcarbonylamino, 1-methyl-1-ethyl-n-pentylcarbonylamino, 1-heptylcarbonylamino, 2-heptylcarbonylamino, 1-ethyl-1,2-dimethyl-n-propylcarbonylamino, 1-ethyl-2,2-dimethyl-n-propylcarbonylamino, 1-octylcarbonylamino, 3-octylcarbonylamino, 4-methyl-3-n-heptylcarbonylamino, 6-methyl-2-n-heptylcarbonylamino, 2-propyl-1-n-heptylcarbonylamino, 2,4,4-trimethyl-1-n-pentylcarbonylamino, 1-nonylcarbonylamino, 2-nonylcarbonylamino, 2,6-dimethyl-4-n-heptylcarbonylamino, 3-ethyl-2,2-dimethyl-3-n-pentylcarbonylamino, 3,5,5-trimethyl-1-n-hexylcarbonylamino, 1-decylcarbonylamino, 2-decylcarbonylamino, 4-decylcarbonylamino, 3,7-dimethyl-1-n-octylcarbonylamino, 3,7-dimethyl-3-n-octylcarbonylamino or the like may be mentioned.
A C1-10 alkylaminocarbonyl group may be a C1-10 monoalkylaminocarbonyl group or a C1-10 dialkylaminocarbonyl group. A C1-10 monoalkylaminocarbonyl group may be linear, branched or a C3-10 cycloalkylaminocarbonyl group, and methylaminocarbonyl, ethylaminocarbonyl, n-propylaminocarbonyl, i-propylaminocarbonyl, c-propylaminocarbonyl, n-butylaminocarbonyl, i-butylaminocarbonyl, s-butylaminocarbonyl, t-butylaminocarbonyl, c-butylaminocarbonyl, 1-methyl-c-propylaminocarbonyl, 2-methyl-c-propylaminocarbonyl, n-pentylaminocarbonyl, 1-methyl-n-butylaminocarbonyl, 2-methyl-n-butylaminocarbonyl, 3-methyl-n-butylaminocarbonyl, 1,1-dimethyl-n-propylaminocarbonyl, 1,2-dimethyl-n-propylaminocarbonyl, 2,2-dimethyl-n-propylaminocarbonyl, 1-ethyl-n-propylaminocarbonyl, c-pentylaminocarbonyl, 1-methyl-c-butylaminocarbonyl, 2-methyl-c-butylaminocarbonyl, 3-methyl-c-butylaminocarbonyl, 1,2-dimethyl-c-propylaminocarbonyl, 2,3-dimethyl-c-propylaminocarbonyl, 1-ethyl-c-propylaminocarbonyl, 2-ethyl-c-propylaminocarbonyl, n-hexylaminocarbonyl, 1-methyl-n-pentylaminocarbonyl, 2-methyl-n-pentylaminocarbonyl, 3-methyl-n-pentylaminocarbonyl, 4-methyl-n-pentylaminocarbonyl, 1,1-dimethyl-n-butylaminocarbonyl, 1,2-dimethyl-n-butylaminocarbonyl, 1,3-dimethyl-n-butylaminocarbonyl, 2,2-dimethyl-n-butylaminocarbonyl, 2,3-dimethyl-n-butylaminocarbonyl, 3,3-dimethyl-n-butylaminocarbonyl, 1-ethyl-n-butylaminocarbonyl, 2-ethyl-n-butylaminocarbonyl, 1,1,2-trimethyl-n-propylaminocarbonyl, 1,2,2-trimethyl-n-propylaminocarbonyl, 1-ethyl-1-methyl-n-propylaminocarbonyl, 1-ethyl-2-methyl-n-propylaminocarbonyl, c-hexylaminocarbonyl, 1-methyl-c-pentylaminocarbonyl, 2-methyl-c-pentylaminocarbonyl, 3-methyl-c-pentylaminocarbonyl, 1-ethyl-c-butylaminocarbonyl, 2-ethyl-c-butylaminocarbonyl, 3-ethyl-c-butylaminocarbonyl, 1,2-dimethyl-c-butylaminocarbonyl, 1,3-dimethyl-c-butylaminocarbonyl, 2,2-dimethyl-c-butylaminocarbonyl, 2,3-dimethyl-c-butylaminocarbonyl, 2,4-dimethyl-c-butylaminocarbonyl, 3,3-dimethyl-c-butylaminocarbonyl, 1-n-propyl-c-propylaminocarbonyl, 2-n-propyl-c-propylaminocarbonyl, 1-i-propyl-c-propylaminocarbonyl, 2-i-propyl-c-propylaminocarbonyl, 1,2,2-trimethyl-c-propylaminocarbonyl, 1,2,3-trimethyl-c-propylaminocarbonyl, 2,2,3-trimethyl-c-propylaminocarbonyl, 1-ethyl-2-methyl-c-propylaminocarbonyl, 2-ethyl-1-methyl-c-propylaminocarbonyl, 2-ethyl-2-methyl-c-propylaminocarbonyl, 2-ethyl-3-methyl-c-propylaminocarbonyl, 1-methyl-1-ethyl-n-pentylaminocarbonyl, 1-heptylaminocarbonyl, 2-heptylaminocarbonyl, 1-ethyl-1,2-dimethyl-n-propylaminocarbonyl, 1-ethyl-2,2-dimethyl-n-propylaminocarbonyl, 1-octylaminocarbonyl, 3-octylaminocarbonyl, 4-methyl-3-n-heptylaminocarbonyl, 6-methyl-2-n-heptylaminocarbonyl, 2-propyl-1-n-heptylaminocarbonyl, 2,4,4-trimethyl-1-n-pentylaminocarbonyl, 1-nonylaminocarbonyl, 2-nonylaminocarbonyl, 2,6-dimethyl-4-n-heptylaminocarbonyl, 3-ethyl-2,2-dimethyl-3-n-pentylaminocarbonyl, 3,5,5-trimethyl-1-n-hexylaminocarbonyl, 1-decylaminocarbonyl, 2-decylaminocarbonyl, 4-decylaminocarbonyl, 3,7-dimethyl-1-n-octylaminocarbonyl, 3,7-dimethyl-3-n-octylaminocarbonyl or the like may be mentioned.
A C1-10 dialkylaminocarbonyl group may be symmetric or asymmetric. A symmetric C1-10 dialkylaminocarbonyl group may be linear, branched or a C3-10 cycloalkylaminocarbonyl group, and dimethylaminocarbonyl, diethylaminocarbonyl, di-n-propylaminocarbonyl, di-i-propylaminocarbonyl, di-c-propylaminocarbonyl, di-n-butylaminocarbonyl, di-i-butylaminocarbonyl, di-s-butylaminocarbonyl, di-t-butylaminocarbonyl, di-c-butylaminocarbonyl, di-(1-methyl-c-propyl)aminocarbonyl, di-(2-methyl-c-propyl)aminocarbonyl, di-n-pentylaminocarbonyl, di-(1-methyl-n-butyl)aminocarbonyl, di-(2-methyl-n-butyl)aminocarbonyl, di-(3-methyl-n-butyl)aminocarbonyl, di-(1,1-dimethyl-n-propyl)aminocarbonyl, di-(1,2-dimethyl-n-propyl)aminocarbonyl, di-(2,2-dimethyl-n-propyl)aminocarbonyl, di-(1-ethyl-n-propyl)aminocarbonyl, di-c-pentylaminocarbonyl, di-(1-methyl-c-butyl)aminocarbonyl, di-(2-methyl-c-butyl)aminocarbonyl, di-(3-methyl-c-butyl)aminocarbonyl, di-(1,2-dimethyl-c-propyl)aminocarbonyl, di-(2,3-dimethyl-c-propyl)aminocarbonyl, di-(1-ethyl-c-propyl)aminocarbonyl, di-(2-ethyl-c-propyl)aminocarbonyl, di-n-hexylaminocarbonyl, di-(1-methyl-n-pentyl)aminocarbonyl, di-(2-methyl-n-pentyl)aminocarbonyl, di-(3-methyl-n-pentyl)aminocarbonyl, di-(4-methyl-n-pentyl)aminocarbonyl, di-(1,1-dimethyl-n-butyl)aminocarbonyl, di-(1,2-dimethyl-n-butyl)aminocarbonyl, di-(1,3-dimethyl-n-butyl)aminocarbonyl, di-(2,2-dimethyl-n-butyl)aminocarbonyl, di-(2,3-dimethyl-n-butyl)aminocarbonyl, di-(3,3-dimethyl-n-butyl)aminocarbonyl, di-(1-ethyl-n-butyl)aminocarbonyl, di-(2-ethyl-n-butyl)aminocarbonyl, di-(1,1,2-trimethyl-n-propyl)aminocarbonyl, di-(1,2,2-trimethyl-n-propyl)aminocarbonyl, di-(1-ethyl-1-methyl-n-propyl)aminocarbonyl, di-(1-ethyl-2-methyl-n-propyl)aminocarbonyl, di-c-hexylaminocarbonyl, di-(1-methyl-c-pentyl)aminocarbonyl, di-(2-methyl-c-pentyl)aminocarbonyl, di-(3-methyl-c-pentyl)aminocarbonyl, di-(1-ethyl-c-butyl)aminocarbonyl, di-(2-ethyl-c-butyl)aminocarbonyl, di-(3-ethyl-c-butyl)aminocarbonyl, di-(1,2-dimethyl-c-butyl)aminocarbonyl, di-(1,3-dimethyl-c-butyl)aminocarbonyl, di-(2,2-dimethyl-c-butyl)aminocarbonyl, di-(2,3-dimethyl-c-butyl)aminocarbonyl, di-(2,4-dimethyl-c-butyl)aminocarbonyl, di-(3,3-dimethyl-c-butyl)aminocarbonyl, di-(1-n-propyl-c-propyl)aminocarbonyl, di-(2-n-propyl-c-propyl)aminocarbonyl, di-(1-i-propyl-c-propyl)aminocarbonyl, di-(2-i-propyl-c-propyl)aminocarbonyl, di-(1,2,2-trimethyl-c-propyl)aminocarbonyl, di-(1,2,3-trimethyl-c-propyl)aminocarbonyl, di-(2,2,3-trimethyl-c-propyl)aminocarbonyl, di-(1-ethyl-2-methyl-c-propyl)aminocarbonyl, di-(2-ethyl-1-methyl-c-propyl)aminocarbonyl, di-(2-ethyl-2-methyl-c-propyl)aminocarbonyl, di-(2-ethyl-3-methyl-c-propyl)aminocarbonyl, di-(1-methyl-1-ethyl-n-pentyl)aminocarbonyl, di-(1-heptyl)aminocarbonyl, di-(2-heptyl)aminocarbonyl, di-(1-ethyl-1,2-dimethyl-n-propyl)aminocarbonyl, di-(1-ethyl-2,2-dimethyl-n-propyl)aminocarbonyl, di-(1-octyl)aminocarbonyl, di-(3-octyl)aminocarbonyl, di-(4-methyl-3-n-heptyl)aminocarbonyl, di-(6-methyl-2-n-heptyl)aminocarbonyl, di-(2-propyl-1-n-heptyl)aminocarbonyl, di-(2,4,4-trimethyl-1-n-pentyl)aminocarbonyl, di-(1-nonyl)aminocarbonyl, di-(2-nonyl)aminocarbonyl, di-(2,6-dimethyl-4-n-heptyl)aminocarbonyl, di-(3-ethyl-2,2-dimethyl-3-n-pentyl)aminocarbonyl, di-(3,5,5-trimethyl-1-n-hexyl)aminocarbonyl, di-(1-decyl)aminocarbonyl, di-(2-decyl)aminocarbonyl, di-(4-decyl)aminocarbonyl, di-(3,7-dimethyl-1-n-octyl)aminocarbonyl, di-(3,7-dimethyl-3-n-octyl)aminocarbonyl or the like may be mentioned.
An asymmetric C1-10 dialkylaminocarbonyl group may be linear, branched or a C3-10 cycloalkyl aminocarbonyl group, and (methyl, ethyl)aminocarbonyl, (methyl, n-propyl)aminocarbonyl, (methyl, i-propyl)aminocarbonyl, (methyl, c-propyl)aminocarbonyl, (methyl, n-butyl)aminocarbonyl, (methyl, i-butyl)aminocarbonyl, (methyl, s-butyl)aminocarbonyl, (methyl, t-butyl)aminocarbonyl, (methyl, n-pentyl)aminocarbonyl, (methyl, c-pentyl)aminocarbonyl, (methyl, n-hexyl)aminocarbonyl, (methyl, c-hexyl)aminocarbonyl, (ethyl, n-propyl)aminocarbonyl, (ethyl, i-propyl)aminocarbonyl, (ethyl, c-propyl)aminocarbonyl, (ethyl, n-butyl)aminocarbonyl, (ethyl, i-butyl)aminocarbonyl, (ethyl, s-butyl)aminocarbonyl, (ethyl, t-butyl)aminocarbonyl, (ethyl, n-pentyl)aminocarbonyl, (ethyl, c-pentyl)aminocarbonyl, (ethyl, n-hexyl)aminocarbonyl, (ethyl, c-hexyl)aminocarbonyl, (n-propyl, i-propyl)aminocarbonyl, (n-propyl, c-propyl)aminocarbonyl, (n-propyl, n-butyl)aminocarbonyl, (n-propyl, i-butyl)aminocarbonyl, (n-propyl, s-butyl)aminocarbonyl, (n-propyl, t-butyl)aminocarbonyl, (n-propyl, n-pentyl)aminocarbonyl, (n-propyl, c-pentyl)aminocarbonyl, (n-propyl, n-hexyl)aminocarbonyl, (n-propyl, c-hexyl)aminocarbonyl, (i-propyl, c-propyl)aminocarbonyl, (i-propyl, n-butyl)aminocarbonyl, (i-propyl, i-butyl)aminocarbonyl, (i-propyl, s-butyl)aminocarbonyl, (i-propyl, t-butyl)aminocarbonyl, (i-propyl, n-pentyl)aminocarbonyl, (i-propyl, c-pentyl)aminocarbonyl, (i-propyl, n-hexyl)aminocarbonyl, (i-propyl, c-hexyl)aminocarbonyl, (c-propyl, n-butyl)aminocarbonyl, (c-propyl, i-butyl)aminocarbonyl, (c-propyl, s-butyl)aminocarbonyl, (c-propyl, t-butyl)aminocarbonyl, (c-propyl, n-pentyl)aminocarbonyl, (c-propyl, c-pentyl)aminocarbonyl, (c-propyl, n-hexyl)aminocarbonyl, (c-propyl, c-hexyl)aminocarbonyl, (n-butyl, i-butyl)aminocarbonyl, (n-butyl, s-butyl)aminocarbonyl, (n-butyl, t-butyl)aminocarbonyl, (n-butyl, n-pentyl)aminocarbonyl, (n-butyl, c-pentyl)aminocarbonyl, (n-butyl, n-hexyl)aminocarbonyl, (n-butyl, c-hexyl)aminocarbonyl, (i-butyl, s-butyl)aminocarbonyl, (i-butyl, t-butyl)aminocarbonyl, (i-butyl, n-pentyl)aminocarbonyl, (i-butyl, c-pentyl)aminocarbonyl, (i-butyl, n-hexyl)aminocarbonyl, (i-butyl, c-hexyl)aminocarbonyl, (s-butyl, t-butyl)aminocarbonyl, (s-butyl, n-pentyl)aminocarbonyl, (s-butyl, c-pentyl)aminocarbonyl, (s-butyl, n-hexyl)aminocarbonyl, (s-butyl, c-hexyl)aminocarbonyl, (t-butyl, n-pentyl)aminocarbonyl, (t-butyl, c-pentyl)aminocarbonyl, (t-butyl, n-hexyl)aminocarbonyl, (t-butyl, c-hexyl)aminocarbonyl, (n-pentyl, c-pentyl)aminocarbonyl, (n-pentyl, n-hexyl)aminocarbonyl, (n-pentyl, c-hexyl)aminocarbonyl, (c-pentyl, n-hexyl)aminocarbonyl, (c-pentyl, c-hexyl)aminocarbonyl, (n-hexyl, c-hexyl)aminocarbonyl, (methyl, n-heptyl)aminocarbonyl, (methyl, n-octyl)aminocarbonyl, (methyl, n-nonyl)aminocarbonyl, (methyl, n-decyl)aminocarbonyl, (methyl, n-heptyl)aminocarbonyl, (ethyl, n-octyl)aminocarbonyl, (ethyl, n-nonyl)aminocarbonyl, (ethyl, n-decyl)aminocarbonyl or the like may be mentioned.
A C1-10 monoalkylamino group may be linear, branched or a C3-10 cycloalkylamino group, and methylamino, ethylamino, n-propylamino, i-propylamino, c-propylamino, n-butylamino, i-butylamino, s-butylamino, t-butylamino, c-butylamino, 1-methyl-c-propylamino, 2-methyl-c-propylamino, n-pentylamino, 1-methyl-n-butylamino, 2-methyl-n-butylamino, 3-methyl-n-butylamino, 1,1-dimethyl-n-propylamino, 1,2-dimethyl-n-propylamino, 2,2-dimethyl-n-propylamino, 1-ethyl-n-propylamino, c-pentylamino, 1-methyl-c-butylamino, 2-methyl-c-butylamino, 3-methyl-c-butylamino, 1,2-dimethyl-c-propylamino, 2,3-dimethyl-c-propylamino, 1-ethyl-c-propylamino, 2-ethyl-c-propylamino, n-hexylamino, 1-methyl-n-pentylamino, 2-methyl-n-pentylamino, 3-methyl-n-pentylamino, 4-methyl-n-pentylamino, 1,1-dimethyl-n-butylamino, 1,2-dimethyl-n-butylamino, 1,3-dimethyl-n-butylamino, 2,2-dimethyl-n-butylamino, 2,3-dimethyl-n-butylamino, 3,3-dimethyl-n-butylamino, 1-ethyl-n-butylamino, 2-ethyl-n-butylamino, 1,1,2-trimethyl-n-propylamino, 1,2,2-trimethyl-n-propylamino, 1-ethyl-1-methyl-n-propylamino, 1-ethyl-2-methyl-n-propylamino, c-hexylamino, 1-methyl-c-pentylamino, 2-methyl-c-pentylamino, 3-methyl-c-pentylamino, 1-ethyl-c-butylamino, 2-ethyl-c-butylamino, 3-ethyl-c-butylamino, 1,2-dimethyl-c-butylamino, 1,3-dimethyl-c-butylamino, 2,2-dimethyl-c-butylamino, 2,3-dimethyl-c-butylamino, 2,4-dimethyl-c-butylamino, 3,3-dimethyl-c-butylamino, 1-n-propyl-c-propylamino, 2-n-propyl-c-propylamino, 1-i-propyl-c-propylamino, 2-i-propyl-c-propylamino, 1,2,2-trimethyl-c-propylamino, 1,2,3-trimethyl-c-propylamino, 2,2,3-trimethyl-c-propylamino, 1-ethyl-2-methyl-c-propylamino, 2-ethyl-1-methyl-c-propylamino, 2-ethyl-2-methyl-c-propylamino, 2-ethyl-3-methyl-c-propylamino, 1-methyl-1-ethyl-n-pentylamino, 1-heptylamino, 2-heptylamino, 1-ethyl-1,2-dimethyl-n-propylamino, 1-ethyl-2,2-dimethyl-n-propylamino, 1-octylamino, 3-octylamino, 4-methyl-3-n-heptylamino, 6-methyl-2-n-heptylamino, 2-propyl-1-n-heptylamino, 2,4,4-trimethyl-1-n-pentylamino, 1-nonylamino, 2-nonylamino, 2,6-dimethyl-4-n-heptylamino, 3-ethyl-2,2-dimethyl-3-n-pentylamino, 3,5,5-trimethyl-1-n-hexylamino, 1-decylamino, 2-decylamino, 4-decylamino, 3,7-dimethyl-1-n-octylamino, 3,7-dimethyl-3-n-octylamino or the like may be mentioned.
A C1-10 dialkylamino group may be symmetric or asymmetric. A symmetric C1-10 dialkylamino group may be linear, branched or a C3-10 cycloalkylamino group, and dimethylamino, diethylamino, di-n-propylamino, di-i-propylamino, di-c-propylamino, di-n-butylamino, di-i-butylamino, di-s-butylamino, di-t-butylamino, di-c-butylamino, di-(1-methyl-c-propyl)amino, di-(2-methyl-c-propyl)amino, di-n-pentylamino, di-(1-methyl-n-butyl)amino, di-(2-methyl-n-butyl)amino, di-(3-methyl-n-butyl)amino, di-(1,1-dimethyl-n-propyl)amino, di-(1,2-dimethyl-n-propyl)amino, di-(2,2-dimethyl-n-propyl)amino, di-(1-ethyl-n-propyl)amino, di-c-pentylamino, di-ti-methyl-c-butyl)amino, di-(2-methyl-c-butyl)amino, di-(3-methyl-c-butyl)amino, di-(1,2-dimethyl-c-propyl)amino, di-(2,3-dimethyl-c-propyl)amino, di-(1-ethyl-c-propyl)amino, di-(2-ethyl-c-propyl)amino, di-n-hexylamino, di-(1-methyl-n-pentyl)amino, di-(2-methyl-n-pentyl)amino, di-(3-methyl-n-pentyl)amino, di-(4-methyl-n-pentyl)amino, di-(1,1-dimethyl-n-butyl)amino, di-(1,2-dimethyl-n-butyl)amino, di-(1,3-dimethyl-n-butyl)amino, di-(2,2-dimethyl-n-butyl)amino, di-(2,3-dimethyl-n-butyl)amino, di-(3,3-dimethyl-n-butyl)amino, di-(1-ethyl-n-butyl)amino, di-(2-ethyl-n-butyl)amino, di-(1,1,2-trimethyl-n-propyl)amino, di-(1,2,2-trimethyl-n-propyl)amino, di-(1-ethyl-1-methyl-n-propyl)amino, di-(1-ethyl-2-methyl-n-propyl)amino, di-c-hexylamino, di-(1-methyl-c-pentyl)amino, di-(2-methyl-c-pentyl)amino, di-(3-methyl-c-pentyl)amino, di-(1-ethyl-c-butyl)amino, di-(2-ethyl-c-butyl)amino, di-(3-ethyl-c-butyl)amino, di-(1,2-dimethyl-c-butyl)amino, di-(1,3-dimethyl-c-butyl)amino, di-(2,2-dimethyl-c-butyl)amino, di-(2,3-dimethyl-c-butyl)amino, di-(2,4-dimethyl-c-butyl)amino, di-(3,3-dimethyl-c-butyl)amino, di-(1-n-propyl-c-propyl)amino, di-(2-n-propyl-c-propyl)amino, di-(1-i-propyl-c-propyl)amino, di-(2-i-propyl-c-propyl)amino, di-(1,2,2-trimethyl-c-propyl)amino, di-(1,2,3-trimethyl-c-propyl)amino, di-(2,2,3-trimethyl-c-propyl)amino, di-(1-ethyl-2-methyl-c-propyl)amino, di-(2-ethyl-1-methyl-c-propyl)amino, di-(2-ethyl-2-methyl-c-propyl)amino, di-(2-ethyl-3-methyl-c-propyl)amino, di-(1-methyl-1-ethyl-n-pentyl)amino, di-(1-heptyl)amino, di-(2-heptyl)amino, di-(1-ethyl-1,2-dimethyl-n-propyl)amino, di-(1-ethyl-2,2-dimethyl-n-propyl)amino, di-(1-octyl)amino, di-(3-octyl)amino, di-(4-methyl-3-n-heptyl)amino, di-(6-methyl-2-n-heptyl)amino, di-(2-propyl-1-n-heptyl)amino, di-(2,4,4-trimethyl-1-n-pentyl)amino, di-(1-nonyl)amino, di-(2-nonyl)amino, di-(2,6-dimethyl-4-n-heptyl)amino, di-(3-ethyl-2,2-dimethyl-3-n-pentyl)amino, di-(3,5,5-trimethyl-1-n-hexyl)amino, di-(1-decyl)amino, di-(2-decyl)amino, di-(4-decyl)amino, di-(3,7-dimethyl-1-n-octyl)amino, di-(3,7-dimethyl-3-n-octyl)amino or the like may be mentioned.
An asymmetric C1-10 dialkylamino group may be linear, branched or a C3-10 cycloalkylamino group, and (methyl, ethyl)amino, (methyl, n-propyl)amino, (methyl, i-propyl)amino, (methyl, c-propyl)amino, (methyl, n-butyl)amino, (methyl, i-butyl)amino, (methyl, s-butyl)amino, (methyl, t-butyl)amino, (methyl, n-pentyl)amino, (methyl, c-pentyl)amino, (methyl, n-hexyl)amino, (methyl, c-hexyl)amino, (ethyl, n-propyl)amino, (ethyl, i-propyl)amino, (ethyl, c-propyl)amino, (ethyl, n-butyl)amino, (ethyl, i-butyl)amino, (ethyl, s-butyl)amino, (ethyl, t-butyl)amino, (ethyl, n-pentyl)amino, (ethyl, c-pentyl)amino, (ethyl, n-hexyl)amino, (ethyl, c-hexyl)amino, (n-propyl, i-propyl)amino, (n-propyl, c-propyl)amino, (n-propyl, n-butyl)amino, (n-propyl, i-butyl)amino, (n-propyl, s-butyl)amino, (n-propyl, t-butyl)amino, (n-propyl, n-pentyl)amino, (n-propyl, c-pentyl)amino, (n-propyl, n-hexyl)amino, (n-propyl, c-hexyl)amino, (i-propyl, c-propyl)amino, (i-propyl, n-butyl)amino, (i-propyl, i-butyl)amino, (i-propyl, s-butyl)amino, (i-propyl, t-butyl)amino, (i-propyl, n-pentyl)amino, (i-propyl, c-pentyl)amino, (i-propyl, n-hexyl)amino, (i-propyl, c-hexyl)amino, (c-propyl, n-butyl)amino, (c-propyl, i-butyl)amino, (c-propyl, s-butyl)amino, (c-propyl, t-butyl)amino, (c-propyl, n-pentyl)amino, (c-propyl, c-pentyl)amino, (c-propyl, n-hexyl)amino, (c-propyl, c-hexyl)amino, (n-butyl, i-butyl)amino, (n-butyl, s-butyl)amino, (n-butyl, t-butyl)amino, (n-butyl, n-pentyl)amino, (n-butyl, c-pentyl)amino, (n-butyl, n-hexyl)amino, (n-butyl, c-hexyl)amino, (i-butyl, s-butyl)amino, (i-butyl, t-butyl)amino, (i-butyl, n-pentyl)amino, (i-butyl, c-pentyl)amino, (i-butyl, n-hexyl)amino, (i-butyl, c-hexyl)amino, (s-butyl, t-butyl)amino, (s-butyl, n-pentyl)amino, (s-butyl, c-pentyl)amino, (s-butyl, n-hexyl)amino, (s-butyl, c-hexyl)amino, (t-butyl, n-pentyl)amino, (t-butyl, c-pentyl)amino, (t-butyl, n-hexyl)amino, (t-butyl, c-hexyl)amino, (n-pentyl, c-pentyl)amino, (n-pentyl, n-hexyl)amino, (n-pentyl, c-hexyl)amino, (c-pentyl, n-hexyl)amino, (c-pentyl, c-hexyl)amino, (n-hexyl, c-hexyl)amino, (methyl, n-heptyl)amino, (methyl, n-octyl)amino, (methyl, n-nonyl)amino, (methyl, n-decyl)amino, (methyl, n-heptyl)amino, (ethyl, n-octyl)amino, (ethyl, n-nonyl)amino, (ethyl, n-decyl)amino or the like may be mentioned.
The protecting group in a protected hydroxyl group may be a C1-4 alkoxymethyl group (such as MOM: methoxymethyl, MEM: 2-methoxyethoxymethyl, ethoxymethyl, n-propoxymethyl, i-propoxymethyl, n-butoxymethyl, iBM: isobutyloxymethyl, BUM: t-butoxymethyl, POM: pivaloyloxymethyl, SEM: trimethylsilylethoxymethyl and the like, preferably a C1-2 alkoxymethyl or the like), an aryloxymethyl (such as BOM: benzyloxymethyl, PMBM: p-methoxybenzyloxymethyl, p-AOM: p-anisyloxymethyl and the like), a C1-4 alkylaminomethyl group (such as dimethylaminomethyl), a substituted acetamidomethyl group (such as Acm: acetamidomethyl, Tacm: trimethylacetamidomethyl and the like), a substituted thiomethyl group (such as MTM: methylthiomethyl, PTM: phenylthiomethyl, Btm: benzylthiomethyl and the like), a carboxyl group, a C1-7 acyl group (such as formyl, acetyl, fluoroacetyl, difluoroacetyl, trifluoroacetyl, chloroacetyl, dichloroacetyl, trichloroacetyl, propionyl, Pv: pivaloyl, tigloyl and the like), an arylcarbonyl group (such as benzoyl, benzoylformyl, benzoylpropionyl, phenylpropionyl and the like), a C1-4 alkoxycarbonyl group (such as methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, i-propoxycarbonyl, n-butoxycarbonyl, i-butoxycarbonyl, BOC: t-butoxycarbonyl, AOC: t-amyloxycarbonyl, VOC: vinyloxycarbonyl, AOC: allyloxycarbonyl, Teoc: 2-(trimethylsilyl)ethoxycarbonyl, Troc: 2,2,2-trichloroethoxycarbonyl and the like, preferably BOC and the like), an aryloxycarbonyl group (such as Z: benzyloxycarbonyl, p-nitrobenzyloxycarbonyl, MOZ: p-methoxybenzyloxycarbonyl and the like), a C1-4 alkylaminocarbonyl group (such as methylcarbamoyl, Ec: ethylcarbamoyl, n-propylcarbamoyl, and the like), an arylaminocarbonyl group (such as phenyl carbamoyl and the like), a trialkylsilyl group (such as TMS: trimethylsilyl, TES: triethylsilyl, TIPS: triisopropylsilyl, DEIPS: diethylisopropylsilyl, DMIPS: dimethylisopropylsilyl, DTBMS: di-t-butylmethylsilyl, IPDMS: isopropyldimethylsilyl, TBDMS: t-butyldimethylsilyl, TDS: thexyldimethylsilyl and the like, preferably t-butyldimethylsilyl and the like), a trialkylarylsilyl group (such as DPMS: diphenylmethylsilyl, TBDPS: t-butyldiphenylsilyl, TBMPS: t-butyldimethoxyphenylsilyl, TPS: triphenylsilyl and the like), an alkylsulfonyl group, (such as Ms: methanesulfonyl, ethanesulfonyl and the like) or an arylsulfonyl group (such as benzenesulfonyl, Ts: p-toluenesulfonyl, p-chlorobenzenesulfonyl, MBS: p-methoxybenzenesulfonyl, m-nitrobenzenesulfonyl, iMds: 2,6-dimethoxy-4-methylbenzenesulfonyl, Mds: 2,6-dimethyl-4-methoxybenzenesulfonyl, Mtb: 2,4,6-trimethoxybenzenesulfonyl, Mte: 2,3,5,6-tetramethyl-4-methoxybenzenesulfonyl, Mtr: 2,3,6-trimethyl-4-methoxybenzenesulfonyl, Mts: 2,4,6-trimethylbenzenesulfonyl, Pme: pentamethylbenzenesulfonyl and the like).
Specific preferred examples of the substituent R1 are a phenyl group, thienyl groups (a 2-thienyl group and a 3-thienyl group), furyl groups (a 2-furyl group and a 3-furyl group), pyridazinyl groups (a 3-pyridazinyl group and a 4-pyridazinyl group), pyridyl groups (a 2-pyridyl group, a 3-pyridyl group and a 4-pyridyl group), quinolyl groups (a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 5-quinolyl group, a 6-quinolyl group, a 7-quinolyl group and a 8-quinolyl group) and isoquinolyl groups (a 1-isoquinolyl group, a 3-isoquinolyl group, a 4-isoquinolyl group, a 5-isoquinolyl group, a 6-isoquinolyl group, a 7-isoquinolyl group and a 8-isoquinolyl group) optionally substituted with one or more of the following substituents.
Substituents: a C1-10 alkyl group, a halogen atom, a C1-10 alkyl group substituted with one or more halogen atoms, a C1-10 alkoxy group substituted with one or more halogen atoms, a nitro group, an amino group, an amino group substituted with one or two C1-10 alkyl groups, an amino group substituted with a C1-10 alkylcarbonyl group, a thiol group substituted with a C1-10 alkyl group, a thiol group substituted with a C1-10 alkylcarbonyl group, a hydroxyl group, a alkoxy group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group and a C1-10 alkylcarbonyl group.
Particularly preferred examples of the substituent R1 are a phenyl group, thienyl groups (a 2-thienyl group and a 3-thienyl group), furyl groups (a 2-furyl group and a 3-furyl group), pyridazinyl groups (a 3-pyridazinyl group and a 4-pyridazinyl group), pyridyl groups (a 2-pyridyl group, a 3-pyridyl group and a 4-pyridyl group), quinolyl groups (a 2-quinolyl group, a 3-quinolyl group, a 4-guinolyl group, a 5-quinolyl group, a 6-quinolyl group, a 7-quinolyl group and a 8-quinolyl group) and isoquinolyl groups (a 1-isoquinolyl group, a 3-isoquinolyl group, a 4-isoquinolyl group, a 5-isoquinolyl group, a 6-isoquinolyl group, a 7-isoquinolyl group and a 8-isoquinolyl group) optionally substituted with one or more of the following substituents.
Substituents: a methyl group, a t-butyl group, a trifluoromethyl group, a trifluoromethoxy group, a chlorine atom, a bromine atom, a fluorine atom, a methoxy group, a methylamino group, a dimethylamino group, a t-butyloxy group and a t-butylamino group.
Still further preferred specific examples of the substituent are a 3-methyl-phenyl group, a 4-methyl-phenyl group, a 3,4-dimethyl-phenyl group, a 3-t-butyl-phenyl group, a 4-t-butyl-phenyl group, a 3-trifluoromethyl-phenyl group, a 4-trifluoromethoxy-phenyl group, a 4-trifluoromethyl-phenyl group, a 3,4-ditrifluoromethyl-phenyl group, a 3-chloro-phenyl group, a 4-chloro-phenyl group, a 4-bromo-phenyl group, a 3-fluoro-phenyl group, a 4-fluoro-phenyl group, a 3,4-dichloro-phenyl group, a 4-methoxy-phenyl group, a 4-methylamino-phenyl group, a 3-methyl-thienyl group, a 4-methyl-thienyl group, a 3,4-dimethyl-thienyl group, a 3-t-butyl-thienyl group, a 4-t-butyl-thienyl group, a 3-trifluoromethyl-thienyl group, a 4-trifluoromethyl-thienyl group, a 3,4-ditrifluoromethyl-thienyl group, a 3-chloro-thienyl group, a 4-chloro-thienyl group, a 3-fluoro-thienyl group, a 4-fluoro-thienyl group, a 3,4-dichloro-thienyl group, a 4-methoxy-thienyl group, a 4-methylamino-thienyl group, a 3-methyl-furyl group, a 4-methyl-furyl group, a 3,4-dimethyl-furyl group, a 3-t-butyl-furyl group, a 4-t-butyl-furyl group, a 3-trifluoromethyl-furyl group, a 4-trifluoromethyl-furyl group, a 3,4-ditrifluoromethyl-furyl group, a 3-chloro-furyl group, a 4-chloro-furyl group, a 3-fluoro-furyl group, a 4-fluoro-furyl group, a 3,4-dichloro-furyl group, a 4-methoxy-furyl group, a 4-methyl-furyl group, a 5-chloro-pyridazinyl group, a 5-methyl-pyridazinyl group, a 5-methoxy-pyridazinyl group, a 4-chloro-pyridazinyl group, a 4-methylpyridazinyl group, a 4-methoxy-pyridazinyl group, a 4-t-butoxy-pyridazinyl group and the like.
Specific preferable examples of L1 are a bond, CH2, an oxygen atom, a sulfur atom, NH, N-Me, N—CHO, CHMe, CMe2, N—CH2Ph and the like, and particularly preferable examples are a bond, CH2, an oxygen atom, a sulfur atom, NH, NMe and the like.
Specific preferable examples of the substituent R2 are a hydrogen atom, a methyl group, an ethyl group, a n-propyl group, an i-propyl group, a t-butyl group, and a phenyl group (the methyl group, the ethyl group, the n-propyl group, the i-propyl group, the t-butyl group and the phenyl group may be optionally substituted with an amino group, a monomethylamino group, a dimethylamino group, a monoethylamino group, a diethylamino group, a methoxy group, an ethoxy group, a methoxycarbonyl group, an ethoxycarbonyl group, a methylcarbonyloxy group, an ethylcarbonyloxy group, a methylcarbonylamino group or an ethylcarbonylamino group and the like), and particularly preferable examples are a hydrogen atom, a methyl group, an ethyl group, a n-propyl group, an i-propyl group, a t-butyl group, a phenyl group and the like.
Specific preferable examples of L2 are a bond, CH2, an oxygen atom, a sulfur atom, NH, N-Me, N—CHO, CHMe, CMe2, N—CH2Ph and the like, and particularly preferable examples are a bond, CH2, an oxygen atom, a sulfur atom, NH, NMe and the like.
Specific preferable examples of L3 are a bond, CH2, an oxygen atom, a sulfur atom, NH, NH—OH, N-Me, N—CHO, CHMe, CMe2, N—CH2PH and the like, and particularly preferred examples are a bond, CH2, an oxygen atom, a sulfur atom, NH, NMe and the like.
Specific preferable examples of X are OH, SH, NH2, OMe, SMe, NHMe, NHEt, NH—CHO, NH—CH2Ph, OCH2Ph, SCH2Ph, OC(═O)CH3, SC(═O)CH3, NHC(═O)CH3 and the like, and particularly preferable examples are OH, SH, NH2 and the like.
Specific preferable examples of Y are an oxygen atom, a sulfur atom, NH, N—OH, N—CHO, N-Me, N—CH2Ph, N-OMe, N—OCH2Ph an the like, and particularly preferred examples are an oxygen atom, a sulfur atom, NH, N—OH and the like.
Specific preferable examples of L4 are a bond, CH2, an oxygen atom, a sulfur atom, NH, N-Me, N—CHO, CHMe, CMe2, N—CH2Ph and the like, and particularly preferred examples are a bond, CH2, an oxygen atom, a sulfur atom, NH, NMe and the like.
Specific preferable examples of the substituent R3 are a methyl group, an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, a s-butyl group, a t-butyl group, a c-propyl group, a c-butyl group, a c-pentyl group, a c-hexyl group, an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, a 1-pentynyl group, a 2-pentynyl group, a 4-pentynyl group, a 1-methyl-2-butynyl group, a 1-methyl-3-butynyl group, a 2-methyl-3-butynyl group, a 3-methyl-1-butynyl group and the following heterocyclic groups optionally substituted with one or more of the following substituents.
Heterocyclic Groups
Substituents: a hydrogen atom, a hydroxyl group, an amino group, a halogen atom, a nitro group, a thiol group, a carboxyl group, a phosphonic acid group, a sulfonic acid group, a carbamoyl group, a hydroxylcarbamoyl group, a cyanocarbamoyl group, a sulfamoyl group, a hydroxysulfamoyl group, a cyanosulfamoyl group, a tetrazole group, a phenyl group, a thienyl group, a pyridyl group, a furyl group, —CH2CO2H, —OCH2CO2H, —NHCH2CO2H, —CH2CH2CO2H, —CH2OH, —OCH2OH, —NHCH2OH, —CH2CH2OH, —(C═O) CO2H, —CH2(C═O)CO2H, —NH(C═O)CO2H, —NHS(═O)2NH2, a C1-10 alkyl group (the C1-10 alkyl group may be substituted with one or more substituents selected from the group consisting of hydroxyl groups, carboxyl groups, the following aryl groups, the following heterocyclic groups and C1-10 alkylamino groups (the C1-10 alkylamino groups may be substituted with one or more of the following aryl groups or one or more of the heterocyclic groups)), a C2-10 alkenyl group, a C2-10 alkynyl group, a C2-9 heterocyclic group, a C1-10 thioalkyl group, a C1-10 alkoxy group, a C1-10 alkylcarbonyl group; a C1-10 alkylaminocarbonyl group, a C1-10 dialkylaminocarbonyl group, a mono- or di-C1-10 alkylamino group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, an aminocarbonyl group, a C1-10 alkylcarbonylamino group (the C1-10 alkoxy group, the C1-10 alkylcarbonyl group, the C1-10 alkylaminocarbonyl group, the C1-10 dialkylaminocarbonyl group, the mono- or di-C1-10 alkylamino group, the C1-10 alkylcarbonyloxy group, the C1-10 alkoxycarbonyl group, the aminocarbonyl group and the C1-10 alkylcarbonylamino group may be substituted with one or more substituents selected from the group consisting of carboxyl groups, carbamoyl groups, sulfamoyl groups, sulfo groups, amino groups, the following aryl groups and the following heterocyclic groups), the following aryl groups and the following heterocyclic groups.
Aryl groups: a phenyl group, thienyl groups (a 2-thienyl group and a 3-thienyl group), furyl groups (a 2-furyl group and a 3-furyl group), pyridazinyl groups (a 3-pyridazinyl group and a 4-pyridazinyl group), pyridyl groups (a 2-pyridyl group, a 3-pyridyl group and 4-pyridyl group), pyrimidinyl groups (a 2-pyrimidinyl group, a 4-pyrimidinyl group and a 5-pyrimidinyl group), quinolyl groups (a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 5-quinolyl group, a 6-quinolyl group, a 7-quinolyl group and a 8-quinolyl group) and isoquinolyl groups (a 1-isoquinolyl group, a 3-isoquinolyl group, a 4-isoquinolyl group, a 5-isoquinolyl group, a 6-isoquinolyl group, a 7-isoquinolyl group and a 8-isoquinolyl group).
Heterocyclic groups: a 1,3,4-oxadiazole group, a 1,3,4-thiadiazole group, a 1,2,4-oxadiazole group, a 1,2,4-thiadiazole group, a 1,2,5-oxadiazole group, a 1,2,5-thiadiazole group, a 1,2-oxazole group and a 1,2-thiazole group.
Still further specific preferable examples of the substituent R3 are a methyl group, an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, a s-butyl group, a t-butyl group, a c-propyl group, a c-butyl group, a c-pentyl group, a c-hexyl group, an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, a 1-pentynyl group, a 2-pentynyl group, a 4-pentynyl group, a 1-methyl-2-butynyl group, a 1-methyl-3-butynyl group, a 2-methyl-3-butynyl group, a 3-methyl-1-butynyl group and the following heterocyclic groups optionally substituted with one or more substituents optionally selected from substituent set A and with one or more substituents optionally selected from substituent set B.
Heterocyclic Groups
Substituent set A: a hydroxyl group, an amino group, a carboxyl group, a phosphonic acid group, a sulfonic acid group, a carbamoyl group, a hydroxycarbamoyl group, a cyanocarbamoyl group, a sulfamoyl group, a hydroxysulfamoyl group, a cyanosulfamoyl group, a tetrazole group, —CH2CO2H, —OCH2CO2H, —NHCH2CO2H, —CH2CH2CO2H and an alkoxycarbonyl group.
Substituent set B: a hydroxyl group, an amino group, a carboxyl group, a phosphonic acid group, a sulfonic acid group, a carbamoyl group, a hydroxycarbamoyl group, a cyanocarbamoyl group, a sulfamoyl group, a nitro group, a cyano group, a halogen atom, a C1-10 alkyl group, a C1-10 alkyl group substituted with one or more fluorine atoms, a sulfamoyl group substituted with a C1-10 alkyl group, a carbamoyl group substituted with a C1-10 alkyl group, a C1-10 alkylcarbonylamino group and a C1-10 alkylaminocarbonyl group (the C1-10 alkylcarbonylamino group and the C1-10 alkylaminocarbonyl group may be substituted with one or more substituents selected from the group consisting of phenyl groups, pyridyl groups, thienyl groups and furyl groups).
Favorable compounds as the thrombopoietin receptor activator, the preventive, therapeutic or improving agent for diseases against which activation of the thrombopoietin receptor is effective and the platelet increasing agent of the present invention are as follows.
1) Compounds represented by the formula (1) wherein A is a nitrogen atom, and B is a sulfur atom, tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
2) Compounds represented by the formula (1) wherein A is a nitrogen atom, and B is an oxygen atom, tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
3) Compounds represented by the formula (1) wherein A is a nitrogen atom, and B is NR9 other than NH (wherein R9 is a hydrogen atom, a hydroxyl group, a formyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkoxy group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkoxy group, the C1-10 alkylcarbonyloxy group, the C1-10 alkoxycarbonyl group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)), a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups) or a C2-14 aryloxy group (the C2-14 aryloxy group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups)), tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
4) Compounds represented by the formula (1) wherein A is CR4 (wherein R4 is a hydrogen atom, a hydroxyl group (the hydroxyl group may be substituted with a C2-6 alkenyl or a C2-6 alkynyl group), a thiol group (the thiol group may be substituted with a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group or a C1-10 alkylcarbonyl group), an amino group (the amino group may be substituted with one or two C2-6 alkenyl groups or one or two C2-6 alkynyl groups), a formyl group, a halogen atom, a nitro group, a cyano group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkylcarbonylamino group, a mono- or di-C1-10 alkylamino group, a C1-10 alkoxy group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkylcarbonylamino group, the mono- or di-C1-10 alkylamino group and the C1-10 alkoxy group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)), a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups), a C2-14 aryloxy group (the C2-14 aryloxy group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyls group, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups), SO2R5, SOR5 or COR5 (wherein R5 is a hydroxyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkoxy group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group and the C1-10 alkoxy group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl group may be substituted with one or more halogen atoms) or one or more halogen atoms)), a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups), a C2-14 aryloxy group (the C2-14 aryloxy group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups) or NR6R7 (wherein each of R6 and R7 is independently a hydrogen atom, a hydroxyl group, a formyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkylcarbonyloxy group, the C1-10 alkoxycarbonyl group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)) or a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups), or R6 and R7 mean, together with each other, —(CH2)m1-E-(CH2)m2— (wherein E is an oxygen atom, a sulfur atom, CR26R27 (wherein each of R26 and R27 is independently a hydrogen atom, a C1-10 alkyl group, a C2-14 aryl group, a C1-10 alkoxy group, a C2-14 aryloxy group, a hydroxyl group or a protected hydroxyl group) or NR8 (wherein R8 is a hydrogen atom, a hydroxyl group, a formyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkoxy group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkoxy group, the C1-10 alkylcarbonyloxy group, the C1-10 alkoxycarbonyl group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)) or a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups)), and each of m1 and m2 is independently an integer of from 0 to 5 provided that m1+m2 is 3, 4 or 5)))), and B is a oxygen atom, tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
5) Compounds represented by the formula (1) wherein A is CR4 (wherein R4 is a hydrogen atom, a hydroxyl group (the hydroxyl group may be substituted with a C2-6 alkenyl or a C2-6 alkynyl group), a thiol group (the thiol group may be substituted with a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group or a C1-10 alkylcarbonyl group), an amino group (the amino group may be substituted with one or two C2-6 alkenyl groups or one or two C2-6 alkynyl groups), a formyl group, a halogen atom, a nitro group, a cyano group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkylcarbonylamino group, a mono- or di-C1-10 alkylamino group, a C1-10 alkoxy group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkylcarbonylamino group, the mono- or di-C1-10 alkylamino group and the C1-10 alkoxy group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl group and the C2-14 aryloxy group may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)), a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups), a C2-14 aryloxy group (the C2-14 aryloxy group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups), SO2R5, SOR5 or COR5 (wherein R5 is a hydroxyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkoxy group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group and the C1-10 alkoxy group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)), a C2-14 aryl group (the C2-14 aryl group, may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups), a C2-14 aryloxy group (the C2-14 aryloxy group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups) or NR6R7 (wherein each of R6 and R7 is independently a hydrogen atom, a hydroxyl group, a formyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkylcarbonyloxy group, the C1-10 alkoxycarbonyl group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)) or a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups), or R6 and R7 mean, together with each other, —(CH2)m1-E-(CH2)m2— (wherein E is an oxygen atom, a sulfur atom, CR26R27 (wherein each of R26 and R27 is independently a hydrogen atom, a C1-10 alkyl group, a C2-14 aryl group, a C1-10 alkoxy group, a C2-14 aryloxy group, a hydroxyl group or a protected hydroxyl group) or NR8 (wherein R8 is a hydrogen atom, a hydroxyl group, a formyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkoxy group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkoxy group, the C1-10 alkylcarbonyloxy group, the C1-10 alkoxycarbonyl group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)) or a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups)), and each of m1 and m2 is independently an integer of from 0 to 5 provided that m1+m2 is 3, 4 or 5)))), and B is a sulfur atom, tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
6) Compounds represented by the formula (1) wherein A is CR4 (wherein R4 is a hydrogen atom, a hydroxyl group (the hydroxyl group may be substituted with a C2-6 alkenyl or a C2-6 alkynyl group), a thiol group (the thiol group may be substituted with a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group or a C1-10 alkylcarbonyl group), an amino group (the amino group may be substituted with one or two C2-6 alkenyl groups or one or two C2-6 alkynyl groups), a formyl group, a halogen atom, a nitro group, a cyano group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkylcarbonylamino group, a mono- or di-C1-10 alkylamino group, a C1-10 alkoxy group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkylcarbonylamino group, the mono- or di-C1-10 alkylamino group and the C1-10 alkoxy group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)), a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups), a C2-14 aryloxy group (the C2-14 aryloxy group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups), SO2R5, SOR5 or COR5 (wherein R5 is a hydroxyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkoxy group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group and the C1-10 alkoxy group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, an amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)), a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups), a C2-14 aryloxy group (the C2-14 aryloxy group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups) or NR6R7 (wherein each of R6 and R7 is independently a hydrogen atom, a hydroxyl group, a formyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkylcarbonyloxy group, the C1-10 alkoxycarbonyl group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)) or a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups), or R6 and R7 mean, together with each other, —(CH2)m1-E-(CH2)m2— (wherein E is an oxygen atom, a sulfur atom, CR26R27 (wherein each of R26 and R27 is independently a hydrogen atom, a C1-10 alkyl group, a C2-14 aryl group, a C1-10 alkoxy group, a C2-14 aryloxy group, a hydroxyl group or a protected hydroxyl group) or NR8 (wherein R8 is a hydrogen atom, a hydroxyl group, a formyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkoxy group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkoxy group, the C1-10 alkylcarbonyloxy group, the C1-10 alkoxycarbonyl group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)) or a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups)), and each of m1 and m2 is independently an integer of from 0 to 5 provided that m1+m2 is 3, 4 or 5)))), and B is NR9 (wherein R9 is a hydrogen atom, a hydroxyl group, a formyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkoxy group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkoxy group, the C1-10 alkylcarbonyloxy group, the C1-10 alkoxycarbonyl group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)), a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups) or a C2-14 aryloxy group (the C2-14 aryloxy group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups)), tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
7) Compounds represented by the formula (1) according to 4), 5) or 6) wherein A is CR37 (wherein R37 is a hydrogen atom, a hydroxyl group (the hydroxyl group may be substituted with a C2-6 alkenyl or a C2-6 alkynyl group), a thiol group (the thiol group may be substituted with a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group or a C1-10 alkylcarbonyl group), an amino group (the amino group may be substituted with one or two C2-6 alkenyl groups or one or two C2-6 alkynyl groups), a formyl group, a halogen atom, a nitro group, a cyano group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkoxy group, a C1-10 alkylcarbonylamino group, a mono- or di-C1-10 alkylamino group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkoxy group, the C1-10 alkylcarbonylamino group and the mono- or di-C1-10 alkylamino group may be substituted with one or more substituents selected from the group consisting of halogen atoms, carboxyl groups, nitro groups and cyano groups), SO2R38, SOR38 or COR38 (wherein R38 is a hydroxyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkoxy group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group and the C1-10 alkoxy group may be substituted with one or more substituents selected from the group consisting of halogen atoms, carboxyl groups, nitro groups and cyano groups), a C2-14 aryl group or a C2-14 aryloxy group (the C2-14 aryl group and the C2-14 aryloxy group may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms))), tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof. The terms in the respective substituents R37 and R38 are the same as those in the respective substituents R1 to R36.
8) Compounds represented by the formula (1) according to 3) or 6) wherein B is NR39 (wherein R39 is a hydrogen atom, a hydroxyl group, a formyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkoxy group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkoxy group, the C1-10 alkylcarbonyloxy group, the C1-10 alkoxycarbonyl group and the C1-10 alkylcarbonyl group may be substituted with one or more substituents selected from the group consisting of carboxyl groups, halogen atoms, nitro groups and cyano groups), a C2-14 aryl group or a C2-14 aryloxy group (the C2-14 aryl group and the C2-14 aryloxy group may be substituted with one or more substituents selected from the group consisting of C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups and halogen atoms)), tautomers prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof. The terms in the substituent R39 are the same as those in the respective substituents R1 to R36.
9) Compounds represented by the formula (1) according to 1), 2), 3), 4), 5), 6), 7) or 8) wherein L1 is a bond, tautomers prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
10) Compounds represented by the formula (1) according to 1), 2), 3), 4), 5), 6), 7), 8) or 9) wherein L2 is a bond, tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
11) Compounds represented by the formula (1) according to 1), 2), 3), 4), 5), 6), 7), 8), 9) or 10) wherein L3 is NR19 (wherein R19 is a hydrogen atom, a hydroxyl group, a formyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkoxy group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkoxy group, the C1-10 alkylcarbonyloxy group, the C1-10 alkoxycarbonyl group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)) or a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups)), tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
12) The compounds according to 1), 2), 3), 4), 5), 6), 7), 8), 9) or 10) wherein L3 is NH, tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
13) The compounds according to 1), 2), 3), 4), 5), 6), 7), 8), 9) or 10) wherein L3 is CH2, tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
14) The compounds according to 11), 12) or 13) wherein R2 is a hydrogen atom, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkoxy group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group and the C1-10 alkoxy group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)), a C2-14 aryl group or a C2-14 aryloxy group (the C2-14 aryl group and the C2-14 aryloxy group may be substituted with one or more C1-6 alkyl groups (the alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms), tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
15) The compounds according to 11), 12) or 13) wherein R2 is a hydrogen atom, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-3 alkoxy group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group and the C1-3 alkoxy group may be optionally substituted with one or more substituents selected from the group consisting, of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, phenyl groups and phenyloxyl groups (the phenyl groups and the phenyloxyl groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms), a phenyl group or a phenyloxy group (the phenyl group and the phenyloxy group may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms), tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
16) The compounds according to 11), 12) or 13) wherein R2 is a hydrogen atom, a C1-10 alkyl group, a C2-6 alkenyl group or a C2-6 alkynyl group (the C1-10 alkyl group, the C2-6 alkenyl group and the C2-6 alkynyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups and protected hydroxyl groups), tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
17) The compounds according to 11), 12) or 13) wherein R2 is a hydrogen atom or a C1-6 alkyl group (the C2-6 alkyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups and protected hydroxyl groups), tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
18) The compounds according to 11), 12) or 13) wherein R2 is a hydrogen atom or a C1-3 alkyl group (the C1-3 alkyl group may be optionally substituted with one or more substituents selected from the group consisting of halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups and protected hydroxyl groups), tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
19) The compounds according to 14), 15), 16), 17) or 18) wherein R1 is a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of halogen atoms, carboxyl groups, nitro groups, formyl groups, cyano groups, hydroxyl groups, protected hydroxyl groups, C1-10 alkyl groups, C2-6 alkenyl groups, C2-6 alkynyl groups, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonyloxy groups (the C1-10 alkyl groups, the C2-6 alkenyl groups, the C2-6 alkynyl groups and the C1-10 alkylcarbonyl groups may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)), C2-14 aryl groups, C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms), thiol groups and amino groups (the thiol groups and the amino groups may be optionally substituted with one or more substituents selected from the group consisting of formyl groups, C1-10 alkyl groups, C2-6 alkenyl groups, C2-6 alkynyl groups and C1-10 alkylcarbonyl groups (the C1-10 alkyl groups, the C2-6 alkenyl groups, the C2-6 alkynyl groups and the C1-10 alkylcarbonyl groups may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)))), tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
20) The compounds according to 14), 15), 16), 17) or 18) wherein R1 is a phenyl group, a thienyl group, a furyl group, a pyridazinyl group, a pyridyl group, a quinolyl group or an isoquinolyl group (the phenyl group, the thienyl group, the furyl group, the pyridazinyl group, the pyridyl group, the quinolyl group and the isoquinolyl group may be optionally substituted with one or more substituents selected from the group consisting of halogen atoms, carboxyl groups, nitro groups, formyl groups, cyano groups, hydroxyl groups, protected hydroxyl groups, C1-10 alkyl groups, C2-6 alkenyl groups, C2-6 alkynyl groups, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonyloxy groups (the C1-10 alkyl groups, the C2-6 alkenyl groups, the C2-6 alkynyl groups, the C1-10 alkoxy groups, the C1-10 alkylcarbonyl groups, the C1-10 alkylcarbonyloxy groups and the C1-10 alkoxycarbonyl groups may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)), thiol groups and amino groups (the thiol groups and the amino groups may be optionally substituted with one or more substituents selected from the group consisting of formyl groups, C1-10 alkyl groups, C2-6 alkenyl groups, C2-6 alkynyl groups and C1-10 alkylcarbonyl groups (the C1-10 alkyl groups, the C2-6 alkenyl groups, the C2-6 alkynyl groups and the C1-10 alkylcarbonyl groups may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)))), tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
21) The compounds according to 14), 15), 16), 17) or 18) wherein R1 is a phenyl group, a thienyl group, a furyl group, a pyridazinyl group, a pyridyl group, a quinolyl group or an isoquinolyl group (the phenyl group, the thienyl group, the furyl group, the pyridazinyl group, the pyridyl group, the quinolyl group and the isoquinolyl group may be optionally substituted with one or more substituents selected from the group consisting of halogen atoms, carboxyl groups, nitro groups, formyl groups, cyano groups, hydroxyl groups, protected hydroxyl groups, C1-10 alkyl groups, C2-6 alkenyl groups, C2-6 alkynyl groups, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonyloxy groups (the C1-10 alkyl groups, the C2-6 alkenyl groups, the C2-6 alkynyl groups, the C1-10 alkoxy groups, the C1-10 alkylcarbonyl groups, the C1-10 alkoxycarbonyl groups and the C1-10 alkylcarbonyloxy groups may be optionally substituted with one or more substituents selected from the group consisting of halogen atoms, carboxyl groups, nitro groups and cyano groups), C2-14 aryl groups, C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms), thiol groups and amino groups (the thiol groups and the amino groups may be optionally substituted with one or more substituents selected from the group consisting of formyl groups, C1-10 alkyl groups, C2-6 alkenyl groups, C2-6 alkynyl groups and C1-10 alkylcarbonyl groups (the C1-10 alkyl groups, the C2-6 alkenyl groups, the C2-6 alkynyl groups and the C1-10 alkylcarbonyl groups may be optionally substituted with one or more substituents selected from the group consisting of halogen atoms, carboxyl groups, nitro groups, cyano groups, hydroxyl groups and protected hydroxyl groups))), tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
22) The compounds according to 14), 15), 16), 17) or 18) wherein R1 is a phenyl group (the phenyl group may be optionally substituted with one or more substituents selected from the group consisting of halogen atoms, carboxyl groups, nitro groups, formyl groups, cyano groups, hydroxyl groups, protected hydroxyl groups, C1-10 alkyl groups, C2-6 alkenyl groups, C2-6 alkynyl groups, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonyloxy groups (the C1-10 alkyl groups, the C2-6 alkenyl groups, the C2-6 alkynyl groups, the C1-10 alkoxy groups, the C1-10 alkylcarbonyl groups, the alkoxycarbonyl groups and the C1-10 alkylcarbonyloxy groups may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)), thiol groups and amino groups (the thiol groups and the amino groups may be optionally substituted with one or more substituents selected from the group consisting of formyl groups, C1-10 alkyl groups, C2-6 alkenyl groups, C2-6 alkynyl groups and C1-10 alkylcarbonyl groups, (the C1-10 alkyl groups, the C2-6 alkenyl groups, the C2-6 alkynyl groups and the C1-10 alkylcarbonyl groups may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl group and the C2-14 aryloxy group may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl group may be substituted with one or more halogen atoms) or one or more halogen atoms)))), tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
23) The compounds according to 14), 15), 16), 17) or 18) wherein R1 is a phenyl group (the phenyl group may be optionally substituted with one or more substituents selected from the group consisting of halogen atoms, carboxyl groups, nitro groups, formyl groups, cyano groups, hydroxyl groups, protected hydroxyl groups, C1-10 alkyl groups, C2-6 alkenyl groups, C2-6 alkynyl groups, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonyloxy groups (the C1-10 alkyl groups, the C2-6 alkenyl groups, the C2-6 alkynyl groups, the C1-10 alkoxy groups, the C1-10 alkylcarbonyl groups, the C1-10 alkoxycarbonyl groups and the C1-10 alkylcarbonyloxy groups may be optionally substituted with one or more substituents selected from the group consisting of halogen atoms, carboxyl groups, nitro groups and cyano groups), C2-14 aryl groups, C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms), thiol groups and amino groups (the thiol groups and the amino groups may be optionally substituted with one or more substituents selected from the group consisting of formyl groups, C1-10 alkyl groups, C2-6 alkenyl groups, C2-6 alkynyl groups and C1-10 alkylcarbonyl groups (the C1-10 alkyl groups, the C2-6 alkenyl groups, the C2-6 alkynyl groups and the C1-10 alkylcarbonyl groups may be optionally substituted with one or more substituents selected from the group consisting of halogen atoms, carboxyl groups, nitro groups, cyano groups, hydroxyl groups and protected hydroxyl groups))), tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
24) The compounds according to 19), 20), 21), 22) or 23) wherein Y is an oxygen atom, tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
25) The compounds according to 19), 20), 21), 22) or 23) wherein Y is a sulfur atom, tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
26) The compounds according to 24) or 25) wherein X is a hydroxyl group, tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
27) The compounds according to 24), 25) or 26) wherein L4 is a bond, and R3 is an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, a s-butyl group, a t-butyl group, a c-propyl group, a c-butyl group, a c-pentyl group, a c-hexyl group, an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, a 1-pentynyl group, a 2-pentynyl group, a 4-pentynyl group, a 1-methyl-2-butynyl group, a 1-methyl-3-butynyl group, a 2-methyl-3-butynyl group, a 3-methyl-1-butynyl group or any one of the following heterocyclic groups:
(the ethyl group, the n-propyl group, the i-propyl group, the n-butyl group, the s-butyl group, the t-butyl group, the c-propyl group, the c-butyl group, the c-pentyl group, the c-hexyl group, the ethynyl group, the 1-propynyl group, the 2-propynyl group, the 1-butynyl group, the 2-butynyl group, the 3-butynyl group, the 1-pentynyl group, the 2-pentynyl group, the 4-pentynyl group, the 1-methyl-2-butynyl group, the 1-methyl-3-butynyl group, the 2-methyl-3-butynyl group, the 3-methyl-1-butynyl group and the above heterocyclic groups may be optionally substituted with one or more substituents selected from the groups consisting of hydroxyl groups, amino groups, thiol groups, carboxyl group, phosphonic acid groups, sulfonic acid groups, carbamoyl groups, hydroxycarbamoyl groups, cyanocarbamoyl groups, sulfamoyl groups, hydroxysulfamoyl groups, cyanosulfamoyl groups, tetrazole groups, —CH2CO2H, groups (a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 5-quinolyl group, a 6-quinolyl group, a 7-quinolyl group and a 8-quinolyl group) and isoquinolyl groups (a 1-isoquinolyl group, a 3-isoquinolyl group, a 4-isoquinolyl group, a 5-isoquinolyl group, a 6-isoquinolyl group, a 7-isoquinolyl group and a 8-isoquinolyl group);
Heterocyclic groups: a 1,3,4-oxadiazole group, a 1,3,4-thiadiazole group, a 1,2,4-oxadiazole group, a 1,2,4-thiadiazole group, a 1,2,5-oxadiazole group, a 1,2,5-thiadiazole group, a 1,2-oxazole group, a 1,2-thiazole group, a 1,3-oxazole group, a 1,3-thiazole group, a pyrrole group, an imidazole group and a pyrazole group), tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
28) The compounds according to 24), 25) or 26) wherein L4 is a bond, and R3 is a methyl group, an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, a s-butyl group, a t-butyl group, a c-propyl group, a c-butyl group, a c-pentyl group, a c-hexyl group, an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, a 1-pentynyl group, a 2-pentynyl group, a 4-pentynyl group, a 1-methyl-2-butynyl group, a 1-methyl-3-butynyl group, a 2-methyl-3-butynyl group, a 3-methyl-1-butynyl group or any one of the following heterocyclic groups:
—OCH2CO2H, —NHCH2CO2H, —CH2CH2CO2H, —CH2OH, —OCH2OH, —NHCH2OH, —CH2CH2OH, C1-10 alkoxycarbonyl groups, C1-10 alkyl groups, C2-10 alkenyl groups, C2-10 alkynyl groups, C2-9 heterocyclic groups, C1-10 alkoxy groups, C1-10 thioalkyl groups, C1-10 alkylcarbonyl groups, mono- or di-C1-10 alkylamino groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups and the following aryl groups and heterocyclic groups (the C1-10 alkyl groups, the C2-10 alkenyl groups, the C2-10 alkynyl groups, the C2-9 heterocyclic groups, the C1-10 alkoxy groups, the C1-10 thioalkyl groups, the C1-10 alkylcarbonyl groups, the mono- or di-C1-10 alkylamino groups, the C1-10 alkylcarbonyloxy groups, the C3-10 alkoxycarbonyl groups, the C1-10 alkylcarbonylamino groups and the following aryl groups and heterocyclic groups may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl groups, carboxyl groups, carbamoyl groups, sulfonic acid groups and sulfamoyl groups):
Aryl groups: a phenyl group, thienyl groups (a thienyl groups (a 2-thienyl group and a 3-thienyl group), furyl groups (a 2-furyl group and a 3-furyl group), pyridazinyl groups (a 3-pyridazinyl group and a 4-pyridazinyl group), pyridyl groups (a 2-pyridyl group, a 3-pyridyl group and a 4-pyridyl group), a pyrazinyl group, pyrimidinyl group (a 2-pyrimidinyl group, a 4-pyrimidinyl group and a 5-pyrimidinyl group), quinolyl
(the methyl group, the ethyl group, the n-propyl group, the i-propyl group, the n-butyl group, the s-butyl group, the t-butyl group, the c-propyl group, the c-butyl group, the c-pentyl group, the c-hexyl group, the ethynyl group, the 1-propynyl group, the 2-propynyl group, the 1-butynyl group, the 2-butynyl group, the 3-butynyl group, the 1-pentynyl group, the 2-pentynyl group, the 4-pentynyl group, the 1-methyl-2-butynyl group, the 1-methyl-3-butynyl group, the 2-methyl-3-butynyl group, the 3-methyl-1-butynyl group and the above heterocyclic groups may be optionally substituted with one or more substituents selected from the groups consisting of hydroxyl groups, amino groups, thiol groups, carboxyl group, phosphonic acid groups, sulfonic acid groups, carbamoyl groups, hydroxycarbamoyl groups, cyanocarbamoyl groups, sulfamoyl groups, hydroxysulfamoyl groups, cyanosulfamoyl groups, tetrazole groups, —CH2CO2H, —OCH2CO2H, —NHCH2CO2H, —CH2CH2CO2H, —CH2OH, —OCH2OH, —NHCH2OH, —CH2CH2OH, C1-10 alkoxycarbonyl groups, C1-10 alkyl groups, C2-10 alkenyl groups, C2-10 alkynyl groups, C2-9 heterocyclic groups, C1-10 alkoxy groups, C1-10 thioalkyl groups, C1-10 alkylcarbonyl groups, mono- or di-C1-10 alkylamino groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylaminocarbonyl groups and C1-10 alkylcarbonylamino groups (the C1-10 alkyl groups, the C2-10 alkenyl groups, the C2-10 alkynyl groups, the C2-9 heterocyclic groups, the C1-10 alkoxy groups, the C1-10 thioalkyl groups, the C1-10 alkylcarbonyl groups, the mono- or di-C1-10 alkylamino groups, the C1-10 alkylcarbonyloxy groups, the C1-10 alkoxycarbonyl groups, the C1-10 alkylaminocarbonyl groups and the C1-10 alkylcarbonylamino groups may be optionally substituted with one or more substituents selected from the group consisting of C2-14 aryl groups, hydroxyl groups, carboxyl groups, carbamoyl groups, sulfonic acid groups and sulfamoyl groups), tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
29) The compounds according to 24), 25) or 26) wherein L4 is a bond, and R3 is a methyl group, an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, a c-propyl group, a c-hexyl group, an ethynyl group, a 1-propynyl group, a 2-propynyl group or a 1-butynyl group (the methyl group, the ethyl group, the n-propyl group, the i-propyl group, the n-butyl group, the c-propyl group, the c-hexyl group, the ethynyl group, the 1-propynyl group, the 2-propynyl group and the 1-butynyl group may be optionally substituted with one or more substituents selected from the groups consisting of hydroxyl groups, amino groups, thiol groups, carboxyl group, phosphonic acid groups, sulfonic acid groups, carbamoyl groups, hydroxycarbamoyl groups, cyanocarbamoyl groups, sulfamoyl groups, hydroxysulfamoyl groups, cyanosulfamoyl groups, tetrazole groups, —CH2CO2H, —OCH2CO2H, —NHCH2CO2H, —CH2CH2CO2H, —CH2OH, —OCH2OH, —NHCH2OH, —CH2CH2OH, C1-10 alkoxycarbonyl groups, C1-10 alkyl groups, C2-10 alkenyl groups, C2-10 alkynyl groups, C2-9 heterocyclic groups, C1-10 alkoxy groups, C1-10 thioalkyl groups, C1-10 alkylcarbonyl groups, mono- or di-C1-10 alkylamino groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups and C1-10 alkylcarbonylamino groups (the C1-10 alkyl groups, the C2-10 alkenyl groups, the C2-10 alkynyl groups, the C2-9 heterocyclic groups, the C1-10 alkoxy groups, the C1-10 thioalkyl groups, the C1-10 alkylcarbonyl groups, the mono- or di-C1-10 alkylamino groups, the C1-10 alkylcarbonyloxy groups, the C1-10 alkoxycarbonyl groups and the C1-10 alkylcarbonylamino groups may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl groups, carboxyl groups, carbamoyl groups, sulfonic acid groups and sulfamoyl groups)), tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
30) The compounds according to 24), 25) or 26) wherein L4 is a bond, and R3 is a methyl group, an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, a c-propyl group, a c-hexyl group, an ethynyl group, a 1-propynyl group, a 2-propynyl group or a 1-butynyl group (the methyl group, the ethyl group, the n-propyl group, the i-propyl group, the n-butyl group, the c-propyl group, the c-hexyl group, the ethynyl group, the 1-propynyl group, the 2-propynyl group and the 1-butynyl group may be optionally substituted with one or more substituents selected from the groups consisting of hydroxyl groups, amino groups, thiol groups, carboxyl group, phosphonic acid groups, sulfonic acid groups, carbamoyl groups, hydroxycarbamoyl groups, cyanocarbamoyl groups, sulfamoyl groups, hydroxysulfamoyl groups, cyanosulfamoyl groups, tetrazole groups, —CH2CO2H, —OCH2CO2H, —NHCH2CO2H, —CH2CH2CO2H, —CH2OH, —OCH2OH, —NHCH2OH, —CH2CH2OH and C1-10 alkoxycarbonyl groups), tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
31) The compounds according to 24), 25) or 26) wherein L4 is a bond, and R3 is any one of the following heterocyclic groups:
(the above heterocyclic groups may be optionally substituted with one or more substituents selected from the group consisting of hydrogen atoms, hydroxyl groups, amino groups, halogen atoms, nitro groups, thiol groups, carboxyl group, phosphonic acid groups, sulfonic acid groups, carbamoyl groups, hydroxycarbamoyl groups, cyanocarbamoyl groups, sulfamoyl groups, hydroxysulfamoyl groups, cyanosulfamoyl groups, tetrazole groups, phenyl groups, thienyl groups, pyridyl groups, furyl groups, —CH2CO2H, —OCH2CO2H, —NHCH2CO2H, —CH2CH2CO2H, —CH2OH, —OCH2OH, —NHCH2OH, —CH2CH2OH, —(C═O)CO2H, —CH2(C═O)CO2H, —NH(C═O)CO2H, —NHS(═O)2NH2, C1-10 alkoxycarbonyl groups, C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more substituents selected from the group consisting of hydroxyl groups, carboxyl groups, phenyl groups, 2-thienyl groups, 3-thienyl groups, 2-furyl groups, 3-furyl groups, 3-pyridazinyl groups, 4-pyridazinyl groups, 2-pyridyl groups, 3-pyridyl groups, 4-pyridyl groups, pyrazinyl groups, 2-pyrimidinyl groups, 4-pyrimidinyl groups, 5-pyrimidinyl groups, 1,3-oxazolyl groups, 1,3-thiazolyl groups, pyrrolyl groups, imidazolyl groups, pyrazolyl groups, 2-quinolyl groups, 3-quinolyl groups, 4-quinolyl groups, 5-quinolyl groups, 6-quinolyl groups, 7-quinolyl groups, 8-quinolyl groups, 1-isoquinolyly groups, 3-isoquinolyly groups, 4-isoquinolyly groups, 5-isoquinolyly groups, 6-isoquinolyly groups, 7-isoquinolyly groups, 8-isoquinolyly groups, 1,3,4-oxadiazole groups, 1,3,4-thiadiazole groups, 1,2,4-oxadiazole groups, 1,2,4-thiadiazole groups, 1,2,5-oxadiazole groups, 1,2,5-thiadiazole groups, 1,2-oxazole groups, 1,2-thiazole groups and C1-10 alkylaminocarbonyl groups (the C1-10 alkylaminocarbonyl groups may be substituted with one or more substituents selected from the group consisting of phenyl groups, 2-thienyl groups, 3-thienyl groups, 2-furyl groups, 3-furyl groups, 3-pyridazinyl groups, 4-pyridazinyl groups, 2-pyridyl groups, 3-pyridyl groups, 4-pyridyl groups, 2-quinolyl groups, 3-quinolyl groups, 4-quinolyl groups, 5-quinolyl groups, 6-quinolyl groups, 7-quinolyl groups, 8-quinolyl groups, 1-isoquinolyly groups, 3-isoquinolyly groups, 4-isoquinolyly groups, 5-isoquinolyly groups, 6-isoquinolyly groups, 7-isoquinolyly groups, 8-isoquinolyly groups, 1,3,4-oxadiazole groups, 1,3,4-thiadiazole groups, 1,2,4-oxadiazole groups, 1,2,4-thiadiazole groups, 1,2,5-oxadiazole groups, 1,2,5-thiadiazole groups, 1,2-oxazole groups, 1,2-thiazole groups, 1,3-oxazole groups, 1,3-thiazole groups, pyrrole groups, imidazole groups and pyrazole groups)), C2-10 alkenyl groups, C2-10 alkynyl groups, C2-9 heterocyclic groups, C1-10 thioalkyl groups, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylaminocarbonyl groups, C1-10 dialkylaminocarbonyl groups, mono- or di-C1-10 alkylamino groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups (the C1-10 alkoxy groups, the C1-10 alkylcarbonyl groups, the C1-10 alkylaminocarbonyl groups, the C1-10 dialkylaminocarbonyl groups, the mono- or di-C1-10 alkylamino groups, the C1-10 alkylcarbonyloxy groups, the C1-10 alkoxycarbonyl groups and the C1-10 alkylcarbonylamino groups may be substituted with one or more substituents selected from the group consisting of carboxyl groups, carbamoyl groups, sulfamoyl groups, sulfo groups, phenyl groups, 2-thienyl groups, 3-thienyl groups, 2-furyl groups, 3-furyl groups, 3-pyridazinyl groups, 4-pyridazinyl groups, 2-pyridyl groups, 3-pyridyl groups, 4-pyridyl groups, 2-quinolyl groups, 3-quinolyl groups, 4-quinolyl groups, 5-quinolyl groups, 6-quinolyl groups, 7-quinolyl groups, 8-quinolyl groups, 1-isoquinolyly groups, 3-isoquinolyly groups, 4-isoquinolyly groups, 5-isoquinolyly groups, 6-isoquinolyly groups, 7-isoquinolyly groups, 8-isoquinolyly groups, 1,3,4-oxadiazole groups, 1,3,4-thiadiazole groups, 1,2,4-oxadiazole groups, 1,2,4-thiadiazole groups, 1,2,5-oxadiazole groups, 1,2,5-thiadiazole groups, 1,2-oxazole groups, 1,2-thiazole groups, 1,3-oxazole groups, 1,3-thiazole groups, pyrrole groups, imidazole groups and pyrazole groups), pyridylaminocarbonyl groups, phenyl groups, 2-thienyl groups, 3-thienyl groups, 2-furyl groups, 3-furyl groups, 3-pyridazinyl groups, 4-pyridazinyl groups, 2-pyridyl groups, 3-pyridyl groups; 4-pyridyl groups, 2-quinolyl groups, 3-quinolyl groups, 4-quinolyl groups, 5-quinolyl groups, 6-quinolyl groups, 7-quinolyl groups, 8-quinolyl groups, 1-isoquinolyly groups, 3-isoquinolyly groups, 4-isoquinolyly groups, 5-isoquinolyly groups, 6-isoquinolyly groups, 7-isoquinolyly groups, 8-isoquinolyly groups, 1,3,4-oxadiazole groups, 1,3,4-thiadiazole groups, 1,2,4-oxadiazole groups, 1,2,4-thiadiazole groups, 1,2,5-oxadiazole groups, 1,2,5-thiadiazole groups, 1,2-oxazole groups, 1,2-thiazole groups, 1,3-oxazole groups, 1,3-thiazole groups, pyrrole groups, imidazole groups and pyrazole groups), tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
32) The compounds according to 24), 25) or 26) wherein L4 is a bond, and R3 is any one of the following heterocyclic groups:
(the above heterocyclic groups may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl groups, amino groups, thiol groups, carboxyl group, phosphonic acid groups, sulfonic acid groups, carbamoyl groups, hydroxycarbamoyl groups, cyanocarbamoyl groups, sulfamoyl groups, hydroxysulfamoyl groups, cyanosulfamoyl groups, tetrazole groups, —CH2CO2H, —OCH2CO2H, —NHCH2CO2H, —CH2CH2CO2H, —CH2OH, —OCH2OH, —NHCH2OH, —CH2CH2OH, C1-10 alkoxycarbonyl groups, C1-10 alkyl groups, C1-10 alkylcarbonyl groups, C1-10 alkylsulfonyl groups, C1-10 alkylaminosulfonyl groups, C1-10 alkylaminocarbonyl groups and C1-10 dialkylaminocarbonyl groups (the C1-10 alkyl groups, the C1-10 alkylcarbonyl groups, the C1-10 alkylsulfonyl groups, the C1-10 alkylaminosulfonyl groups, the C1-10 alkylaminocarbonyl groups and the C1-10 dialkylaminocarbonyl groups may be substituted with one or more substituents selected from the group consisting of phenyl groups, thienyl groups, furyl groups, pyridyl groups, nitro groups, cyano groups, hydroxyl groups, amino groups, carboxyl groups, phosphonic acid groups, sulfonic acid groups, carbamoyl groups, sulfamoyl groups and tetrazole groups)), tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
33) The compounds according to 24), 25) or 26) wherein L4 is a bond, and R3 is any one of the following heterocyclic groups:
(the above heterocyclic groups may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl groups, amino groups, thiol groups, carboxyl group, phosphonic acid groups, sulfonic acid groups, carbamoyl groups, hydroxycarbamoyl groups, cyanocarbamoyl groups, sulfamoyl groups, hydroxysulfamoyl groups, cyanosulfamoyl groups, tetrazole groups, —CH2CO2H, —OCH2CO2H, —NHCH2CO2H, —CH2CH2CO2H, —CH2OH, —OCH2OH, —NHCH2OH, —CH2CH2OH, C1-10 alkoxycarbonyl groups, C1-10 alkyl groups, C2-10 alkenyl groups, C2-10 alkynyl groups, C2-9 heterocyclic groups, C1-10 alkoxy groups, C1-10 thioalkyl groups, C1-10 alkylcarbonyl groups, mono- or di-C1-10 alkylamino groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups and C1-10 alkylcarbonylamino groups (the C1-10 alkyl groups, the C2-10 alkenyl groups, the C2-10 alkynyl groups, the C2-9 heterocyclic groups, the C1-10 alkoxy groups, the C1-10 thioalkyl groups, the C1-10 alkylcarbonyl groups, the mono- or di-C1-10 alkylamino groups, the C1-10 alkylcarbonyloxy groups, the C1-10 alkoxycarbonyl groups and the C1-10 alkylcarbonylamino groups may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl groups, carboxyl groups, carbamoyl groups, sulfonic acid groups and sulfamoyl groups)), tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
34) The compounds according to 24), 25) or 26) wherein L4 is a bond, and R3 is any one of the following heterocyclic groups:
(the above heterocyclic groups are optionally substituted with one or more substituents selected from the group consisting of hydroxyl groups, amino groups, thiol groups, carboxyl group, phosphonic acid groups, sulfonic acid groups, carbamoyl groups, hydroxycarbamoyl groups, cyanocarbamoyl groups, sulfamoyl groups, hydroxysulfamoyl groups, cyanosulfamoyl groups, tetrazole groups, —CH2CO2H, —OCH2CO2H, —NHCH2CO2H, —CH2CH2CO2H, —CH2OH, —OCH2OH, —NHCH2OH, —CH2CH2OH, C1-10 alkoxycarbonyl groups, methyl groups, ethyl groups, n-propyl groups, i-propyl groups, methylcarbonyl groups, ethylcarbonyl groups, n-propylcarbonyl groups, methylsulfonyl groups, ethylsulfonyl groups, n-propylsulfonyl groups, i-propyl sulfonyl groups, methylaminosulfonyl groups, ethylaminosulfonyl groups, n-propylaminosulfonyl groups, i-propylaminosulfonyl groups, methylaminocarbonyl groups, ethylaminocarbonyl groups, n-propylaminocarbonyl groups, i-propylaminocarbonyl groups, c-propylaminocarbonyl groups and n-butylaminocarbonyl groups (the methyl groups, the ethyl groups, the n-propyl groups, the i-propyl groups, the methylcarbonyl groups, the ethylcarbonyl groups, the n-propylcarbonyl groups, the methylsulfonyl groups, the ethylsulfonyl groups, the n-propylsulfonyl groups, the i-propylsulfonyl groups, the methylaminosulfonyl groups, the ethylaminosulfonyl groups, the n-propylaminosulfonyl groups, the i-propylaminosulfonyl groups, the methylaminocarbonyl groups, the ethylaminocarbonyl groups, the n-propylaminocarbonyl groups, the i-propylaminocarbonyl groups, the c-propylaminocarbonyl groups and the n-butylaminocarbonyl groups may be substituted with one or more substituents selected from the group consisting of phenyl groups, thienyl groups, pyridyl groups and furyl groups)), tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
35) The compounds according to 24), 25) or 26) wherein L4 is NR22 (wherein R22 is a hydrogen atom, a hydroxyl group, a formyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkoxy group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkoxy group, the C1-10 alkylcarbonyloxy group, the C1-10 alkoxycarbonyl group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)) or a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups)), and R3 is an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, a s-butyl group, a t-butyl group, a c-propyl group, a c-butyl group, a c-pentyl group, a c-hexyl group, an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, a 1-pentynyl group, a 2-pentynyl group, a 4-pentynyl group, a 1-methyl-2-butynyl group, a 1-methyl-3-butynyl group, a 2-methyl-3-butynyl group, a 3-methyl-1-butynyl group or any one of the following heterocyclic groups:
(the ethyl group, the n-propyl group, the i-propyl group, the n-butyl group, the s-butyl group, the t-butyl group, the c-propyl group, the c-butyl group, the c-pentyl group, the c-hexyl group, the ethynyl group, the 1-propynyl group, the 2-propynyl group, the 1-butynyl group, the 2-butynyl group, the 3-butynyl group, the 1-pentynyl group, the 2-pentynyl group, the 4-pentynyl group, the 1-methyl-2-butynyl group, the 1-methyl-3-butynyl group, the 2-methyl-3-butynyl group, the 3-methyl-1-butynyl group and the above heterocyclic groups may be optionally substituted with one or more substituents selected from the groups consisting of hydroxyl groups, amino groups, thiol groups, carboxyl group, phosphonic acid groups, sulfonic acid groups, carbamoyl groups, hydroxycarbamoyl groups, cyanocarbamoyl groups, sulfamoyl groups, hydroxysulfamoyl groups, cyanosulfamoyl groups, tetrazole groups, —CH2CO2H, —OCH2CO2H, —NHCH2CO2H, —CH2CH2CO2H, —CH2OH, —OCH2OH, —NHCH2OH, —CH2CH2OH, C1-10 alkoxycarbonyl groups, C1-10 alkyl groups, C2-10 alkenyl groups, C2-10 alkynyl groups, C2-9 heterocyclic groups, C1-10 alkoxy groups, C1-10 thioalkyl groups, C1-10 alkylcarbonyl groups, mono- or di-C1-10 alkylamino groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups and C1-10 alkylcarbonylamino groups (the C1-10 alkyl groups, the C2-10 alkenyl groups, the C2-10 alkynyl groups, the C2-9 heterocyclic groups, the C1-10 alkoxy groups, the C1-10 thioalkyl groups, the C1-10 alkylcarbonyl groups, the mono- or di-C1-10 alkylamino groups, the C1-10 alkylcarbonyloxy groups, the C1-10 alkoxycarbonyl groups and the C1-10 alkylcarbonylamino groups may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl groups, carboxyl groups, carbamoyl groups, sulfonic acid groups and sulfamoyl groups):
Aryl groups: a phenyl group, thienyl groups (a 2-thienyl group and a 3-thienyl group), furyl groups (a 2-furyl group and a 3-furyl group), pyridazinyl groups (a 3-pyridazinyl group and a 4-pyridazinyl group), pyridyl groups (a 2-pyridyl group, a 3-pyridyl group and a 4-pyridyl group), quinolyl groups (a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 5-quinolyl group, a 6-quinolyl group, a 7-quinolyl group and a 8-quinolyl group) and isoquinolyl groups (a 1-isoquinolyl group, a 3-isoquinolyl group, a 4-isoquinolyl group, a 5-isoquinolyl group, a 6-isoquinolyl group, a 7-isoquinolyl group and a 8-isoquinolyl group);
Heterocyclic groups: a 1,3,4-oxadiazole group, a 1,3,4-thiadiazole group, a 1,2,4-oxadiazole group, a 1,2,4-thiadiazole group, a 1,2,5-oxadiazole group, a 1,2,5-thiadiazole group, a 1,2-oxazole group and a 1,2-thiazole group), tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
36) The compounds according to 24), 25) or 26) wherein L4 is NR22 (wherein R22 is a hydrogen atom, a hydroxyl group, a formyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkoxy group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkoxy group, the C1-10 alkylcarbonyloxy group, the C1-10 alkoxycarbonyl group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)) or a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups)), and R3 is a methyl group, an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, a s-butyl group, a t-butyl group, a c-propyl group, a c-butyl group, a c-pentyl group, a c-hexyl group, an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, a 1-pentynyl group, a 2-pentynyl group, a 4-pentynyl group, a 1-methyl-2-butynyl group, a 1-methyl-3-butynyl group, a 2-methyl-3-butynyl group, a 3-methyl-1-butynyl group or any one of the following heterocyclic groups:
(the methyl group, the ethyl group, the n-propyl group, the i-propyl group, the n-butyl group, the s-butyl group, the t-butyl group, the c-propyl group, the c-butyl group, the c-pentyl group, the c-hexyl group, the ethynyl group, the 1-propynyl group, the 2-propynyl group, the 1-butynyl group, the 2-butynyl group, the 3-butynyl group, the 1-pentynyl group, the 2-pentynyl group, the 4-pentynyl group, the 1-methyl-2-butynyl group, the 1-methyl-3-butynyl group, the 2-methyl-3-butynyl group, the 3-methyl-1-butynyl group and the above heterocyclic groups may be optionally substituted with one or more substituents selected from the groups consisting of hydroxyl groups, amino groups, thiol groups, carboxyl group, phosphonic acid groups, sulfonic acid groups, carbamoyl groups, hydroxycarbamoyl groups, cyanocarbamoyl groups, sulfamoyl groups, hydroxysulfamoyl groups, cyanosulfamoyl groups, tetrazole groups, —CH2CO2H, —OCH2CO2H, —NHCH2CO2H, —CH2CH2CO2H, —CH2OH, —OCH2OH, —NHCH2OH, —CH2CH2OH, C1-10 alkoxycarbonyl groups, C1-10 alkyl groups, C2-10 alkenyl groups, C2-10 alkynyl groups, C2-9 heterocyclic groups, C1-10 alkoxy groups, C1-10 thioalkyl groups, C1-10 alkylcarbonyl groups, mono- or di-C1-10 alkylamino groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups and C1-10 alkylcarbonylamino groups (the C1-10 alkyl groups, the C2-10 alkenyl groups, the C2-10 alkynyl groups, the C2-9 heterocyclic groups, the C1-10 alkoxy groups, the C1-10 thioalkyl groups, the C1-10 alkylcarbonyl groups, the mono- or di-C1-10 alkylamino groups, the C1-10 alkylcarbonyloxy groups, the C1-10 alkoxycarbonyl groups and the C1-10 alkylcarbonylamino groups may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl groups, carboxyl groups, carbamoyl groups, sulfonic acid groups and sulfamoyl groups)), tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
37) The compounds according to 24), 25) or 26) wherein L4 is NR22 (wherein R22 is a hydrogen atom, a hydroxyl group, a formyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkoxy group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkoxy group, the C1-10 alkylcarbonyloxy group, the C1-10 alkoxycarbonyl group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)) or a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups)), and R3 is a methyl group, an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, a c-propyl group, a c-hexyl group, an ethynyl group, a 1-propynyl group, a 2-propynyl group or a 1-butynyl group (the methyl group, the ethyl group, the n-propyl group, the i-propyl group, the n-butyl group, the c-propyl group, the c-hexyl group, the ethynyl group, the 1-propynyl group, the 2-propynyl group and the 1-butynyl group may be optionally substituted with one or more substituents selected from the groups consisting of hydroxyl groups, amino groups, thiol groups, carboxyl group, phosphonic acid groups, sulfonic acid groups, carbamoyl groups, hydroxycarbamoyl groups, cyanocarbamoyl groups, sulfamoyl groups, hydroxysulfamoyl groups, cyanosulfamoyl groups, tetrazole groups, —CH2CO2H, —OCH2CO2H, —NHCH2CO2H, —CH2CH2CO2H, —CH2OH, —OCH2OH, —NHCH2OH, —CH2CH2OH, C1-10 alkoxycarbonyl groups, C1-10 alkyl groups, C2-10 alkenyl groups, C2-10 alkynyl groups, C2-9 heterocyclic groups, C1-10 alkoxy groups, C1-10 thioalkyl groups, C1-10 alkylcarbonyl groups, mono- or di-C1-10 alkylamino groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups and C1-10 alkylcarbonylamino groups (the C1-10 alkyl groups, the C2-10 alkenyl groups, the C2-10 alkynyl groups, the C2-9 heterocyclic groups, the C1-10 alkoxy groups, the C1-10 thioalkyl groups, the C1-10 alkylcarbonyl groups, the mono- or di-C1-10 alkylamino groups, the C1-10 alkylcarbonyloxy groups, the C1-10 alkoxycarbonyl groups and the C1-10 alkylcarbonylamino groups may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl groups, carboxyl groups, carbamoyl groups, sulfonic acid groups and sulfamoyl groups)), tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
38) The compounds according to 24), 25) or 26) wherein L4 is NR22 (wherein R22 is a hydrogen atom, a hydroxyl group, a formyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkoxy group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkoxy group, the C1-10 alkylcarbonyloxy group, the C1-10 alkoxycarbonyl group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)) or a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups)), and R3 is a methyl group, an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, a c-propyl group, a c-hexyl group, an ethynyl group, a 1-propynyl group, a 2-propynyl group or a 1-butynyl group (the methyl group, the ethyl group, the n-propyl group, the i-propyl group, the n-butyl group, the c-propyl group, the c-hexyl group, the ethynyl group, the 1-propynyl group, the 2-propynyl group and the 1-butynyl group may be optionally substituted with one or more substituents selected from the groups consisting of hydroxyl groups, amino groups, thiol groups, carboxyl group, phosphonic acid groups, sulfonic acid groups, carbamoyl groups, hydroxycarbamoyl groups, cyanocarbamoyl groups, sulfamoyl groups, hydroxysulfamoyl groups, cyanosulfamoyl groups, tetrazole groups, —CH2CO2H, —OCH2CO2H, —NHCH2CO2H, —CH2CH2CO2H, —CH2OH, —OCH2OH, —NHCH2OH, —CH2CH2OH and C1-10 alkoxycarbonyl groups), tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
39) The compounds according to 24), 25) or 26) wherein L4 is NR22 (wherein R22 is a hydrogen atom, a hydroxyl group, a formyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkoxy group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkoxy group, the C1-10 alkylcarbonyloxy group, the C1-10 alkoxycarbonyl group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)) or a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups)), and R3 is any one of the following heterocyclic groups:
(the above heterocyclic groups may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl groups, amino groups, thiol groups, carboxyl group, phosphonic acid groups, sulfonic acid groups, carbamoyl groups, hydroxycarbamoyl groups, cyanocarbamoyl groups, sulfamoyl groups, hydroxysulfamoyl groups, cyanosulfamoyl groups, tetrazole groups, —CH2CO2H, —OCH2CO2H, —NHCH2CO2H, —CH2CH2CO2H, —CH2OH, —OCH2OH, —NHCH2OH, —CH2CH2OH, C1-10 alkoxycarbonyl groups, C1-10 alkyl groups, C2-10 alkenyl groups, C2-10 alkynyl groups, C2-9 heterocyclic groups, C1-10 alkoxy groups, C1-10 thioalkyl groups, C1-10 alkylcarbonyl groups, mono- or di-C1-10 alkylamino groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups and C1-10 alkylcarbonylamino groups (the C1-10 alkyl groups, the C2-10 alkenyl groups, the C2-10 alkynyl groups, the C2-9 heterocyclic groups, the C1-10 alkoxy groups, the C1-10 thioalkyl groups, the C1-10 alkylcarbonyl groups, the mono- or di-C1-10 alkylamino groups, the C1-10 alkylcarbonyloxy groups, the C1-10 alkoxycarbonyl groups and the C1-10 alkylcarbonylamino groups may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl groups, carboxyl groups, carbamoyl groups, sulfonic acid groups and sulfamoyl groups)), tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
40) The compounds according to 24), 25) or 26) wherein L4 is NR22 (wherein R22 is a hydrogen atom, a hydroxyl group, a formyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkoxy group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkoxy group, the C1-10 alkylcarbonyloxy group, the C1-10 alkoxycarbonyl group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)) or a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups)), and R3 is any one of the following heterocyclic groups:
(the above heterocyclic groups may be optionally substituted with one or more substituents selected from the groups consisting of hydroxyl groups, amino groups, thiol groups, carboxyl group, phosphonic acid groups, sulfonic acid groups, carbamoyl groups, hydroxycarbamoyl groups, cyanocarbamoyl groups, sulfamoyl groups, hydroxysulfamoyl groups, cyanosulfamoyl groups, tetrazole groups, —CH2CO2H, —OCH2CO2H, —NHCH2CO2H, —CH2CH2CO2H, —CH2OH, —OCH2OH, —NHCH2OH, —CH2CH2OH and C1-10 alkoxycarbonyl groups), tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
41) The compounds according to 24), 25) or 26) wherein L4 is NR22 (wherein R22 is a hydrogen atom, a hydroxyl group, a formyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkoxy group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkoxy group, the C1-10 alkylcarbonyloxy group, the C1-10 alkoxycarbonyl group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)) or a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups)), and R3 is any one of the following heterocyclic groups:
(the above heterocyclic groups may be optionally substituted with one or more substituents selected from the groups consisting of hydroxyl groups, amino groups, thiol groups, carboxyl group, phosphonic acid groups, sulfonic acid groups, carbamoyl groups, hydroxycarbamoyl groups, cyanocarbamoyl groups, sulfamoyl groups, hydroxysulfamoyl groups, cyanosulfamoyl groups, tetrazole groups, —CH2CO2H, —OCH2CO2H, —NHCH2CO2H, —CH2CH2CO2H, —CH2OH, —OCH2OH, —NHCH2OH, —CH2CH2OH, C1-10 alkoxycarbonyl groups, C1-10 alkyl groups, C2-10 alkenyl groups, C2-10 alkynyl groups, C2-9 heterocyclic groups, C1-10 alkoxy groups, C1-10 thioalkyl groups, C1-10 alkylcarbonyl groups, mono- or di-C1-10 alkylamino groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups and C1-10 alkylcarbonylamino groups (the C1-10 alkyl groups, the C2-10 alkenyl groups, the C2-10 alkynyl groups, the C2-9 heterocyclic groups, the C1-10 alkoxy groups, the C1-10 thioalkyl groups, the C1-10 alkylcarbonyl groups, the mono- or di-C1-10 alkylamino groups, the C1-10 alkylcarbonyloxy groups, the C1-10 alkoxycarbonyl groups and the C1-10 alkylcarbonylamino groups may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl groups, carboxyl groups, carbamoyl groups, sulfonic acid groups and sulfamoyl groups)), tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
42) The compounds according to 24), 25) or 26) wherein L4 is NR22 (wherein R22 is a hydrogen atom, a hydroxyl group, a formyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-10 alkoxy group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkoxy group, the C1-10 alkylcarbonyloxy group, the C1-10 alkoxycarbonyl group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups (the C2-14 aryl groups and the C2-14 aryloxy groups may be substituted with one or more C1-6 alkyl groups (the C1-6 alkyl groups may be substituted with one or more halogen atoms) or one or more halogen atoms)) or a C2-14 aryl group (the C2-14 aryl group may be optionally substituted with one or more substituents selected from the group consisting of C1-10 alkyl groups (the C1-10 alkyl groups may be substituted with one or more halogen atoms), C2-6 alkenyl groups, C2-6 alkynyl groups, carboxyl groups, nitro groups, cyano groups, halogen atoms, C1-10 alkoxy groups, C1-10 alkylcarbonyl groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups, amino groups, mono- or di-C1-10 alkylamino groups, hydroxyl groups, protected hydroxyl groups, C2-14 aryl groups and C2-14 aryloxy groups)), and R3 is any one of the following heterocyclic groups:
(the above heterocyclic groups may be optionally substituted with one or more substituents selected from the groups consisting of hydroxyl groups, amino groups, thiol groups, carboxyl group, phosphonic acid groups, sulfonic acid groups, carbamoyl groups, hydroxycarbamoyl groups, cyanocarbamoyl groups, sulfamoyl groups, hydroxysulfamoyl groups, cyanosulfamoyl groups, tetrazole groups, —CH2CO2H, —OCH2CO2H, —NHCH2CO2H, —CH2CH2CO2H, —CH2OH, —OCH2OH, —NHCH2OH, —CH2CH2OH and C1-10 alkoxycarbonyl groups), tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
43) The compounds according to 24), 25) or 26) wherein L4 is NH, and R3 is an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, a s-butyl group, a t-butyl group, a c-propyl group, a c-butyl group, a c-pentyl group, a c-hexyl group, an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, a 1-pentynyl group, a 2-pentynyl group, a 4-pentynyl group, a 1-methyl-2-butynyl group, a 1-methyl-3-butynyl group, a 2-methyl-3-butynyl group, a 3-methyl-1-butynyl group or any one of the following heterocyclic groups:
(the ethyl group, the n-propyl group, the i-propyl group, the n-butyl group, the s-butyl group, the t-butyl group, the c-propyl group, the c-butyl group, the c-pentyl group, the c-hexyl group, the ethynyl group, the 1-propynyl group, the 2-propynyl group, the 1-butynyl group, the 2-butynyl group, the 3-butynyl group, the 1-pentynyl group, the 2-pentynyl group, the 4-pentynyl group, the 1-methyl-2-butynyl group, the 1-methyl-3-butynyl group, the 2-methyl-3-butynyl group, the 3-methyl-1-butynyl group and the above heterocyclic groups may be optionally substituted with one or more substituents selected from the groups consisting of hydroxyl groups, amino groups, thiol groups, carboxyl group, phosphonic acid groups, sulfonic acid groups, carbamoyl groups, hydroxycarbamoyl groups, cyanocarbamoyl groups, sulfamoyl groups, hydroxysulfamoyl groups, cyanosulfamoyl groups, tetrazole groups, —CH2CO2H, —OCH2CO2H, —NHCH2CO2H, —CH2CH2CO2H, —CH2OH, —OCH2OH, —NHCH2OH, —CH2CH2OH, C1-10 alkoxycarbonyl groups, C1-10 alkyl groups, C2-10 alkenyl groups, C2-10 alkynyl groups, C2-9 heterocyclic groups, C1-10 alkoxy groups, C1-10 thioalkyl groups, C1-10 alkylcarbonyl groups, mono- or di-C1-10 alkylamino groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups and the following aryl groups and heterocyclic groups (the C1-10 alkyl groups, the C2-10 alkenyl groups, the C2-10 alkynyl groups, the C2-9 heterocyclic groups, the C1-10 alkoxy groups, the C1-10 thioalkyl groups, the C1-10 alkylcarbonyl groups, the mono- or di-C1-10 alkylamino groups, the C1-10 alkylcarbonyloxy groups, the C1-10 alkoxycarbonyl groups, the C1-10 alkylcarbonylamino groups and the following aryl groups and heterocyclic groups may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl groups, carboxyl groups, carbamoyl groups, sulfonic acid groups and sulfamoyl groups):
Aryl groups: a phenyl group, thienyl groups (a 2-thienyl group and a 3-thienyl group), furyl groups (a 2-furyl group and a 3-furyl group), pyridazinyl groups (a 3-pyridazinyl group and a 4-pyridazinyl group), pyridyl groups (a 2-pyridyl group, a 3-pyridyl group and a 4-pyridyl group), quinolyl groups (a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 5-quinolyl group, a 6-quinolyl group, a 7-quinolyl group and a 8-quinolyl group) and isoquinolyl groups (a 1-isoquinolyl group, a 3-isoquinolyl group, a 4-isoquinolyl group, a 5-isoquinolyl group, a 6-isoquinolyl group, a 7-isoquinolyl group and a 8-isoquinolyl group);
Heterocyclic groups: a 1,3,4-oxadiazole group, a 1,3,4-thiadiazole group, a 1,2,4-oxadiazole group, a 1,2,4-thiadiazole group, a 1,2,5-oxadiazole group, a 1,2,5-thiadiazole group, a 1,2-oxazole group and a 1,2-thiazole group),
tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
44) The compounds according to 24), 25) or 26) wherein L4 is NH, and R3 is a methyl group, an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, a s-butyl group, a t-butyl group, a c-propyl group, a c-butyl group, a c-pentyl group, a c-hexyl group, an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, a 1-pentynyl group, a 2-pentynyl group, a 4-pentynyl group, a 1-methyl-2-butynyl group, a 1-methyl-3-butynyl group, a 2-methyl-3-butynyl group, a 3-methyl-1-butynyl group or any one of the following heterocyclic groups:
(the methyl group, the ethyl group, the n-propyl group, the i-propyl group, the n-butyl group, the s-butyl group, the t-butyl group, the c-propyl group, the c-butyl group, the c-pentyl group, the c-hexyl group, the ethynyl group, the 1-propynyl group, the 2-propynyl group, the 1-butynyl group, the 2-butynyl group, the 3-butynyl group, the 1-pentynyl group, the 2-pentynyl group, the 4-pentynyl group, the 1-methyl-2-butynyl group, the 1-methyl-3-butynyl group, the 2-methyl-3-butynyl group, the 3-methyl-1-butynyl group and the above heterocyclic groups may be optionally substituted with one or more substituents selected from the groups consisting of hydroxyl groups, amino groups, thiol groups, carboxyl group, phosphonic acid groups, sulfonic acid groups, carbamoyl groups, hydroxycarbamoyl groups, cyanocarbamoyl groups, sulfamoyl groups, hydroxysulfamoyl groups, cyanosulfamoyl groups, tetrazole groups, —CH2CO2H, —OCH2CO2H, —NHCH2CO2H, —CH2CH2CO2H, —CH2OH, —OCH2OH, —NHCH2OH, —CH2CH2OH, C1-10 alkoxycarbonyl groups, C1-10 alkyl groups, C2-10 alkenyl groups, C2-10 alkynyl groups, C2-9 heterocyclic groups, C1-10 alkoxy groups, C1-10 thioalkyl groups, C1-10 alkylcarbonyl groups, mono- or di-C1-10 alkylamino groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups and C1-10 alkylcarbonylamino groups (the C1-10 alkyl groups, the C2-10 alkenyl groups, the C2-10 alkynyl groups, the C2-9 heterocyclic groups, the C1-10 alkoxy groups, the C1-10 thioalkyl groups, the C1-10 alkylcarbonyl groups, the mono- or di-C1-10 alkylamino groups, the C1-10 alkylcarbonyloxy groups, the C1-10 alkoxycarbonyl groups and the C1-10 alkylcarbonylamino groups may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl groups, carboxyl groups, carbamoyl groups, sulfonic acid groups and sulfamoyl groups)), tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
45) The compounds according to 24), 25) or 26) wherein L4 is NH, and R3 is a methyl group, an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, a c-propyl group, a c-hexyl group, an ethynyl group, a 1-propynyl group, a 2-propynyl group or a 1-butynyl group (the methyl group, the ethyl group, the n-propyl group, the i-propyl group, the n-butyl group, the c-propyl group, the c-hexyl group, the ethynyl group, the 1-propynyl group, the 2-propynyl group and the 1-butynyl group may be optionally substituted with one or more substituents selected from the groups consisting of hydroxyl groups, amino groups, thiol groups, carboxyl group, phosphonic acid groups, sulfonic acid groups, carbamoyl groups, hydroxycarbamoyl groups, cyanocarbamoyl groups, sulfamoyl groups, hydroxysulfamoyl groups, cyanosulfamoyl groups, tetrazole groups, —CH2CO2H, —OCH2CO2H, —NHCH2CO2H, —CH2CH2CO2H, —CH2OH, —OCH2OH, —NHCH2OH, —CH2CH2OH, C1-10 alkoxycarbonyl groups, C1-10 alkyl groups, C2-10 alkenyl groups, C1-10 alkynyl groups, C2-9 heterocyclic groups, C1-10 alkoxy groups, C1-10 thioalkyl groups, C1-10 alkylcarbonyl groups, mono- or di-C1-10 alkylamino groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups and C1-10 alkylcarbonylamino groups (the C1-10 alkyl groups, the C2-10 alkenyl groups, the C2-10 alkynyl groups, the C2-9 heterocyclic groups, the C1-10 alkoxy groups, the C1-10 thioalkyl groups, the C1-10 alkylcarbonyl groups, the mono- or di-C1-10 alkylamino groups, the C1-10 alkylcarbonyloxy groups, the C1-10 alkoxycarbonyl groups and the C1-10 alkylcarbonylamino groups may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl groups, carboxyl groups, carbamoyl groups, sulfonic acid groups and sulfamoyl groups)), tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
46) The compounds according to 24), 25) or 26) wherein L4 is NH, and R3 is a methyl group, an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, a c-propyl group, a c-hexyl group, an ethynyl group, a 1-propynyl group, a 2-propynyl group or a 1-butynyl group (the methyl group, the ethyl group, the n-propyl group, the i-propyl group, the n-butyl group, the c-propyl group, the c-hexyl group, the ethynyl group, the 1-propynyl group, the 2-propynyl group and the 1-butynyl group may be optionally substituted with one or more substituents selected from the groups consisting of hydroxyl groups, amino groups, thiol groups, carboxyl group, phosphonic acid groups, sulfonic acid groups, carbamoyl groups, hydroxycarbamoyl groups, cyanocarbamoyl groups, sulfamoyl groups, hydroxysulfamoyl groups, cyanosulfamoyl groups, tetrazole groups, —CH2CO2H, —OCH2CO2H, —NHCH2CO2H, —CH2CH2CO2H, —CH2OH, —OCH2OH, —NHCH2OH, —CH2CH2OH and C1-10 alkoxycarbonyl groups), tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
47) The compounds according to 24), 25) or 26) wherein L4 is NH, and R3 is any one of the following heterocyclic groups:
(the above heterocyclic groups may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl groups, amino groups, thiol groups, carboxyl group, phosphonic acid groups, sulfonic acid groups, carbamoyl groups, hydroxycarbamoyl groups, cyanocarbamoyl groups, sulfamoyl groups, hydroxysulfamoyl groups, cyanosulfamoyl groups, tetrazole groups, —CH2CO2H, —OCH2CO2H, —NHCH2CO2H, —CH2CH2CO2H, —CH2OH, —OCH2OH, —NHCH2OH, —CH2CH2OH, C1-10 alkoxycarbonyl groups, C1-10 alkyl groups, C2-10 alkenyl groups, C2-10 alkynyl groups, C2-9 heterocyclic groups, C1-10 alkoxy groups, C1-10 thioalkyl groups, C1-10 alkylcarbonyl groups, mono- or di-C1-10 alkylamino groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups and C1-10 alkylcarbonylamino groups (the C1-10 alkyl groups, the C2-10 alkenyl groups, the C2-10 alkynyl groups, the C2-9 heterocyclic groups, the C1-10 alkoxy groups, the C1-10 thioalkyl groups, the C1-10 alkylcarbonyl groups, the mono- or di-C1-10 alkylamino groups, the C1-10 alkylcarbonyloxy groups, the C1-10 alkoxycarbonyl groups and the C1-10 alkylcarbonylamino groups may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl groups, carboxyl groups, carbamoyl groups, sulfonic acid groups and sulfamoyl groups)), tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
48) The compounds according to 24), 25) or 26) wherein L4 is NH, and R3 is any one of the following heterocyclic groups:
(the above heterocyclic groups may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl groups, amino groups, thiol groups, carboxyl group, phosphonic acid groups, sulfonic acid groups, carbamoyl groups, hydroxycarbamoyl groups, cyanocarbamoyl groups, sulfamoyl groups, hydroxysulfamoyl groups, cyanosulfamoyl groups, tetrazole groups, —CH2CO2H, —OCH2CO2H, —NHCH2CO2H, —CH2CH2CO2H, —CH2OH, —OCH2OH, —NHCH2OH, —CH2CH2OH and C1-10 alkoxycarbonyl groups), tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
49) The compounds according to 24), 25) or 26) wherein L4 is NH, and R3 is any one of the following heterocyclic groups:
(the above heterocyclic groups may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl groups, amino groups, thiol groups, carboxyl group, phosphonic acid groups, sulfonic acid groups, carbamoyl groups, hydroxycarbamoyl groups, cyanocarbamoyl groups, sulfamoyl groups, hydroxysulfamoyl groups, cyanosulfamoyl groups, tetrazole groups, —CH2CO2H, —OCH2CO2H, —NHCH2CO2H, —CH2CH2CO2H, —CH2OH, —OCH2OH, —NHCH2OH, —CH2CH2OH, C1-10 alkoxycarbonyl groups, C1-10 alkyl groups, C2-10 alkenyl groups, C2-10 alkynyl groups, C2-9 heterocyclic groups, C1-10 alkoxy groups, C1-10 thioalkyl groups, C1-10 alkylcarbonyl groups, mono- or di-C1-10 alkylamino groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups and C1-10 alkylcarbonylamino groups (the C1-10 alkyl groups, the C2-10 alkenyl groups, the C2-10 alkynyl groups, the C2-9 heterocyclic groups, the C1-10 alkoxy groups, the C1-10 thioalkyl groups, the C1-10 alkylcarbonyl groups, the mono- or di-C1-10 alkylamino groups, the C1-10 alkylcarbonyloxy groups, the C1-10 alkoxycarbonyl groups and the C1-10 alkylcarbonylamino groups may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl groups, carboxyl groups, carbamoyl groups, sulfonic acid groups and sulfamoyl groups)), tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
50) The compounds according to 24), 25) or 26) wherein L4 is NH, and R3 is any one of the following heterocyclic groups:
(the above heterocyclic groups may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl groups, amino groups, thiol groups, carboxyl group, phosphonic acid groups, sulfonic acid groups, carbamoyl groups, hydroxycarbamoyl groups, cyanocarbamoyl groups, sulfamoyl groups, hydroxysulfamoyl groups, cyanosulfamoyl groups, tetrazole groups, —CH2CO2H, —OCH2CO2H, —NHCH2CO2H, —CH2CH2CO2H, —CH2OH, —OCH2OH, —NHCH2OH, —CH2CH2OH and C1-10 alkoxycarbonyl groups), tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
51) The compounds according to 24), 25) or 26) wherein L4 is an oxygen atom or a sulfur atom, and R3 is an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, a s-butyl group, a t-butyl group, a c-propyl group, a c-butyl group, a c-pentyl group, a c-hexyl group, an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, a 1-pentynyl group, a 2-pentynyl group, a 4-pentynyl group, a 1-methyl-2-butynyl group, a 1-methyl-3-butynyl group, a 2-methyl-3-butynyl group, a 3-methyl-1-butynyl group or any one of the following heterocyclic groups:
(the ethyl group, the n-propyl group, the i-propyl group, the n-butyl group, the s-butyl group, the t-butyl group, the c-propyl group, the c-butyl group, the c-pentyl group, the c-hexyl group, the ethynyl group, the 1-propynyl group, the 2-propynyl group, the 1-butynyl group, the 2-butynyl group, the 3-butynyl group, the 1-pentynyl group, the 2-pentynyl group, the 4-pentynyl group, the 1-methyl-2-butynyl group, the 1-methyl-3-butynyl group, the 2-methyl-3-butynyl group, the 3-methyl-1-butynyl group and the above heterocyclic groups may be optionally substituted with one or more substituents selected from the groups consisting of hydroxyl groups; amino groups, thiol groups, carboxyl group, phosphonic acid groups, sulfonic acid groups, carbamoyl groups, hydroxycarbamoyl groups, cyanocarbamoyl groups, sulfamoyl groups, hydroxysulfamoyl groups, cyanosulfamoyl groups, tetrazole groups, —CH2CO2H, —OCH2CO2H, —NHCH2CO2H, —CH2CH2CO2H, —CH2OH, —OCH2OH, —NHCH2OH, —CH2CH2OH, C1-10 alkoxycarbonyl groups, C1-10 alkyl groups, C2-10 alkenyl groups, C2-10 alkynyl groups, C2-9 heterocyclic groups, C1-10 alkoxy groups, C1-10 thioalkyl groups, C1-10 alkylcarbonyl groups, mono- or di-C1-10 alkylamino groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups, C1-10 alkylcarbonylamino groups and the following aryl groups and heterocyclic groups (the C1-10 alkyl groups, the C2-10 alkenyl groups, the C2-10 alkynyl groups, the C2-10 heterocyclic groups, the C1-10 alkoxy groups, the C1-10 thioalkyl groups, the C1-10 alkylcarbonyl groups, the mono- or di-C1-10 alkylamino groups, the C1-10 alkylcarbonyloxy groups, the C1-10 alkoxycarbonyl groups, the C1-10 alkylcarbonylamino groups and the following aryl groups and heterocyclic groups may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl groups, carboxyl groups, carbamoyl groups, sulfonic acid groups and sulfamoyl groups):
Aryl groups: a phenyl group, thienyl groups (a 2-thienyl group and a 3-thienyl group), furyl groups (a 2-furyl group and a 3-furyl group), pyridazinyl groups (a 3-pyridazinyl group and a 4-pyridazinyl group), pyridyl groups (a 2-pyridyl group, a 3-pyridyl group and a 4-pyridyl group), quinolyl groups (a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 5-quinolyl group, a 6-quinolyl group, a 7-quinolyl group and a 8-quinolyl group) and isoquinolyl groups (a 1-isoquinolyl group, a 3-isoquinolyl group, a 4-isoquinolyl group, a 5-isoquinolyl group, a 6-isoquinolyl group, a 7-isoquinolyl group and a 8-isoquinolyl group);
Heterocyclic groups: a 1,3,4-oxadiazole group, a 1,3,4-thiadiazole group, a 1,2,4-oxadiazole group, a 1,2,4-thiadiazole group, a 1,2,5-oxadiazole group, a 1,2,5-thiadiazole group, a 1,2-oxazole group and a 1,2-thiazole group), tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
52) The compounds according to 24), 25) or 26) wherein L4 is an oxygen atom or a sulfur atom, and R3 is a methyl group, an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, a s-butyl group, a t-butyl group, a c-propyl group, a c-butyl group, a c-pentyl group, a c-hexyl group, an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, a 1-pentynyl group, a 2-pentynyl group, a 4-pentynyl group, a 1-methyl-2-butynyl group, a 1-methyl-3-butynyl group, a 2-methyl-3-butynyl group, a 3-methyl-1-butynyl group or any one of the following heterocyclic groups:
(the methyl group, the ethyl group, the n-propyl group, the i-propyl group, the n-butyl group, the s-butyl group, the t-butyl group, the c-propyl group, the c-butyl group, the c-pentyl group, the c-hexyl group, the ethynyl group, the 1-propynyl group, the 2-propynyl group, the 1-butynyl group, the 2-butynyl group, the 3-butynyl group, the 1-pentynyl group, the 2-pentynyl group, the 4-pentynyl group, the 1-methyl-2-butynyl group, the 1-methyl-3-butynyl group, the 2-methyl-3-butynyl group, the 3-methyl-1-butynyl group and the above heterocyclic groups may be optionally substituted with one or more substituents selected from the groups consisting of hydroxyl groups, amino groups, thiol groups, carboxyl group, phosphonic acid groups, sulfonic acid groups, carbamoyl groups, hydroxycarbamoyl groups, cyanocarbamoyl groups, sulfamoyl groups, hydroxysulfamoyl groups, cyanosulfamoyl groups, tetrazole groups, —CH2CO2H, —OCH2CO2H, —NHCH2CO2H, —CH2CH2CO2H, —CH2OH, —OCH2OH, —NHCH2OH, —CH2CH2OH, C1-10 alkoxycarbonyl groups, C1-10 alkyl groups, C2-10 alkenyl groups, C2-10 alkynyl groups, C2-9 heterocyclic groups, C1-10 alkoxy groups, C1-10 thioalkyl groups, C1-10 alkylcarbonyl groups, mono- or di-C1-10 alkylamino groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups and C1-10 alkylcarbonylamino groups (the C1-10 alkyl groups, the C2-10 alkenyl groups, the C2-10 alkynyl groups, the C2-9 heterocyclic groups, the C1-10 alkoxy groups, the C1-10 thioalkyl groups, the C1-10 alkylcarbonyl groups, the mono- or di-C1-10 alkylamino groups, the C1-10 alkylcarbonyloxy groups, the C1-10 alkoxycarbonyl groups and the C1-10 alkylcarbonylamino groups may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl groups, carboxyl groups, carbamoyl groups, sulfonic acid groups and sulfamoyl groups)), tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
53) The compounds according to 24), 25) or 26) wherein L4 is an oxygen atom or a sulfur atom, and R3 is a methyl group, an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, a c-propyl group, a c-hexyl group, an ethynyl group, a 1-propynyl group, a 2-propynyl group or a 1-butynyl group (the methyl group, the ethyl group, the n-propyl group, the i-propyl group, the n-butyl group, the c-propyl group, the c-hexyl group, the ethynyl group, the 1-propynyl group, the 2-propynyl group and the 1-butynyl group may be optionally substituted with one or more substituents selected from the groups consisting of hydroxyl groups, amino groups, thiol groups, carboxyl group, phosphonic acid groups, sulfonic acid groups, carbamoyl groups, hydroxycarbamoyl groups, cyanocarbamoyl groups, sulfamoyl groups, hydroxysulfamoyl groups, cyanosulfamoyl groups, tetrazole groups, —CH2CO2H, —OCH2CO2H, —NHCH2CO2H, —CH2CH2CO2H, —CH2OH, —OCH2OH, —NHCH2OH, —CH2CH2OH, C1-10 alkoxycarbonyl groups, C1-10 alkyl groups, C2-10 alkenyl groups, C2-10 alkynyl groups, C2-9 heterocyclic groups, C1-10 alkoxy groups, C1-10 thioalkyl groups, C1-10 alkylcarbonyl groups, mono- or di-C1-10 alkylamino groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups and C1-10 alkylcarbonylamino groups (the C1-10 alkyl groups, the C2-10 alkenyl groups, the C2-10 alkynyl groups, the C2-9 heterocyclic groups, the C1-10 alkoxy groups, the C1-10 thioalkyl groups, the C1-10 alkylcarbonyl groups, the mono- or di-C1-10 alkylamino groups, the C1-10 alkylcarbonyloxy groups, the C1-10 alkoxycarbonyl groups and the C1-10 alkylcarbonylamino groups may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl groups, carboxyl groups, carbamoyl groups, sulfonic acid groups and sulfamoyl groups)), tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
54) The compounds according to 24), 25) or 26) wherein L4 is an oxygen atom or a sulfur atom, and R3 is a methyl group, an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, a c-propyl group, a c-hexyl group, an ethynyl group, a 1-propynyl group, a 2-propynyl group or a 1-butynyl group (the methyl group, the ethyl group, the n-propyl group, the i-propyl group, the n-butyl group, the c-propyl group, the c-hexyl group, the ethynyl group, the 1-propynyl group, the 2-propynyl group and the 1-butynyl group may be optionally substituted with one or more substituents selected from the groups consisting of hydroxyl groups, amino groups, thiol groups, carboxyl group, phosphonic acid groups, sulfonic acid groups, carbamoyl groups, hydroxycarbamoyl groups, cyanocarbamoyl groups, sulfamoyl groups, hydroxysulfamoyl groups, cyanosulfamoyl groups, tetrazole groups, —CH2CO2H, —OCH2CO2H, —NHCH2CO2H, —CH2CH2CO2H, —CH2OH, —OCH2OH, —NHCH2OH, —CH2CH2OH and C1-10 alkoxycarbonyl groups), tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
55) The compounds according to 24), 25) or 26) wherein L4 is an oxygen atom or a sulfur atom, and R3 is any one of the following heterocyclic groups:
(the above heterocyclic groups may be optionally substituted with one or more substituents selected from the groups consisting of hydroxyl groups, amino groups, thiol groups, carboxyl group, phosphonic acid groups, sulfonic acid groups, carbamoyl groups, hydroxycarbamoyl groups, cyanocarbamoyl groups, sulfamoyl groups, hydroxysulfamoyl groups, cyanosulfamoyl groups, tetrazole groups, —CH2CO2H, —OCH2CO2H, —NHCH2CO2H, —CH2CH2CO2H, —CH2OH, —OCH2OH, —NHCH2OH, —CH2CH2OH, C1-10 alkoxycarbonyl groups, C1-10 alkyl groups, C2-10 alkenyl groups, C2-10 alkynyl groups, C2-9 heterocyclic groups, C1-10 alkoxy groups, C1-10 thioalkyl groups, C1-10 alkylcarbonyl groups, mono- or di-C1-10 alkylamino groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups and C1-10 alkylcarbonylamino groups (the C1-10 alkyl groups, the C2-10 alkenyl groups, the C2-10 alkynyl groups, the C2-6 heterocyclic groups, the C1-10 alkoxy groups, the C1-10 thioalkyl groups, the C1-10 alkylcarbonyl groups, the mono- or di-C1-10 alkylamino groups, the C1-10 alkylcarbonyloxy groups, the C1-10 alkoxycarbonyl groups and the C1-10 alkylcarbonylamino groups may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl groups, carboxyl groups, carbamoyl groups, sulfonic acid groups and sulfamoyl groups)), tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
56) The compounds according to 24), 25) or 26) wherein L4 is an oxygen atom or a sulfur atom, and R3 is any one of the following heterocyclic groups:
(the above heterocyclic groups may be optionally substituted with one or more substituents selected from the groups consisting of hydroxyl groups, amino groups, thiol groups, carboxyl group, phosphonic acid groups, sulfonic acid groups, carbamoyl groups, hydroxycarbamoyl groups, cyanocarbamoyl groups, sulfamoyl groups, hydroxysulfamoyl groups, cyanosulfamoyl groups, tetrazole groups, —CH2CO2H, —OCH2CO2H, —NHCH2CO2H, —CH2CH2CO2H, —CH2OH, —OCH2OH, —NHCH2OH, —CH2CH2OH and C1-10 alkoxycarbonyl groups), tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
57) The compounds according to 24), 25) or 26) wherein L4 is an oxygen atom or a sulfur atom, and R3 is any one of the following heterocyclic groups:
(the above heterocyclic groups may be optionally substituted with one or more substituents selected from the groups consisting of hydroxyl groups, amino groups, thiol groups, carboxyl group, phosphonic acid groups, sulfonic acid groups, carbamoyl groups, hydroxycarbamoyl groups, cyanocarbamoyl groups, sulfamoyl groups, hydroxysulfamoyl groups, cyanosulfamoyl groups, tetrazole groups, —CH2CO2H, —OCH2CO2H, —NHCH2CO2H, —CH2CH2CO2H, —CH2OH, —OCH2OH, —NHCH2OH, —CH2CH2OH, C1-10 alkoxycarbonyl groups, C1-10 alkyl groups, C2-10 alkenyl groups, C2-10 alkynyl groups, C2-9 heterocyclic groups, C1-10 alkoxy groups, C1-10 thioalkyl groups, C1-10 alkylcarbonyl groups, mono- or di-C1-10 alkylamino groups, C1-10 alkylcarbonyloxy groups, C1-10 alkoxycarbonyl groups and C1-10 alkylcarbonylamino groups (the C1-10 alkyl groups, the C2-10 alkenyl groups, the C2-10 alkynyl groups, the C2-9 heterocyclic groups, the C1-10 alkoxy groups, the C1-10 thioalkyl groups, the C1-10 alkylcarbonyl groups, the mono- or di-C1-10 alkylamino groups, the C1-10 alkylcarbonyloxy groups, the C1-10 alkoxycarbonyl groups and the C1-10 alkylcarbonylamino groups may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl groups, carboxyl groups, carbamoyl groups, sulfonic acid groups and sulfamoyl groups)), tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
58) The compounds according to 24), 25) or 26) wherein L4 is an oxygen atom or a sulfur atom, and R3 is any one of the following heterocyclic groups:
(the above heterocyclic groups may be optionally substituted with one or more substituents selected from the groups consisting of hydroxyl groups, amino groups, thiol groups, carboxyl group, phosphonic acid groups, sulfonic acid groups, carbamoyl groups, hydroxycarbamoyl groups, cyanocarbamoyl groups, sulfamoyl groups, hydroxysulfamoyl groups, cyanosulfamoyl groups, tetrazole groups, —CH2CO2H, —OCH2CO2H, —NHCH2CO2H, —CH2CH2CO2H, —CH2OH, —OCH2OH, —NHCH2OH, —CH2CH2OH and C1-10 alkoxycarbonyl groups), tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
59) The compounds wherein A, B, R1, L1, R2, L2, L3, Y, L4, R3 and X are any of the following combinations in Table 1, tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof. The symbols in Table 1 denote the flowing substituents.
60) The compounds wherein A, B, R1, L1, R2, L2, L3, Y, L4, R3 and X are any of the following combinations in Table 2, tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof. The symbols in Table 2 denote the flowing substituents.
61) The compounds wherein A, B, R1, L1, R2, L2, L3, Y, L4, R3 and X are any of the following combinations in Table 2, tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof (provided that in the case of 61), Q1a, Q1b, Q1c, Q1i, Q1j, T3a, T3b, T3c, T3d, T3e, Q3e, T3f, T3g, T3h, T3i and T3j in Table 2 denote the following substituents).
62) The compounds wherein A, B, R1, L1, R2, L2, L3, Y, L4, R3 and X are any of the following combinations in Table 3, tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof. The symbols in Table 3 denote the flowing substituents.
63) The compounds wherein A, B, R1, L1, R2, L2, L3, Y, L4, R3 and X are any of the following combinations in Table 3, tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof (provided that in the case of 63), Q1a, Q1b and Q3a in Table 3 denote the following substituents).
64) The compounds wherein A, B, R1, L1, R2, L2, L3, Y, L4, R3 and X are any of the following combinations in Table 2, tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof (provided that in the case of 64), Q1a, Q1b, Q1c, Q1i, Q1j, T3a, T3b, T3c, T3d, T3e, Q3e, T3f, T3g, T3h, T3i and T3j in Table 2 denote the following substituents).
65) The compounds wherein A, B, R1, L1, R2, L2, L3, Y, L4, R3 and X are any of the following combinations in Table 1, tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof (provided that in the case of 65), Q1a, Q1b, Q1c, Q1d, Q1e, Q1f, Q1g, Q1h, Q1i, Q1j, Q1k, Q1l, Q1m, Q1n, Q1k′, Q1l′, Q1m′, Q1n′, Q3a, Q3b, Q3c, Q3d, Q3e, Q3f, Q3g and Q3h in Table 1 denote the following substituents).
66) The compounds wherein A, B, R1, L1, R2, L2, L3, Y, L4, R3 and X are any of the following combinations in Table 1, tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof (provided that in the case of 66), Q1a, Q1b, Q1c, Q1d, Q1e, Q1f, Q1g, Q1h, Q1i, Q1j, Q1k, Q1l, Q1m, Q1n, Q1k′, Q1l′, Q1m′, Q1n′, Q3a, Q3b, Q3c, Q3d, Q3e, Q3f, Q3g and Q3h in Table 1 denote the following substituents).
67) The compounds wherein A, B, R1, L1, R2, L2, L3, Y, L4, R3 and X are any of the following combinations in Table 1, tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof (provided that in the case of 67), Q1a, Q1b, Q1c, Q1d, Q1e, Q1f, Q1g, Q1h, Q1i, Q1j, Q1k, Q1l, Q1m, Q1n, Q1k′, Q1l′, Q1m′, Q1n′, Q3a, Q3b, Q3c, Q3d, Q3e, Q3f, Q3g and Q3h in Table 1 denote the following substituents).
68) The compounds wherein A, B, R1, L1, R2, L2, L3, Y, L4, R3 and X are any of the following combinations in Table 1, tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof (provided that in the case of 68), Q1a, Q1b, Q1c, Q1d, Q1e, Q1f, Q1g, Q1h, Q1i, Q1j, Q1k, Q1l, Q1m, Q1n, Q1k′, Q1l′, Q1m′, Q1n′, Q3a, Q3b, Q3c, Q3d, Q3e, Q3f, Q3g and Q3h in Table 1 denote the following substituents).
69) The compounds wherein A, B, R1, L1, R2, L2, L3, Y, L4, R3 and X are any of the following combinations in Table 1, tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof (provided that in the case of 69), Q1a, Q1b, Q1c, Q1d, Q1e, Q1f, Q1g, Q1h, Q1i, Q1j, Q1k, Q1l, Q1m, Q1n, Q1k′, Q1l′, Q1m′, Q1n′, Q3a, Q3b, Q3c, Q3d, Q3e, Q3f, Q3g and Q3h in Table 1 denote the following substituents).
70) The compounds wherein A, B, R1, L1, R2, L2, L3, Y, L4, R3 and X are any of the following combinations in Table 1, tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof (provided that in the case of 70), Q1a, Q1b, Q1c, Q1d, Q1e, Q1f, Q1g, Q1h, Q1i, Q1j, Q1k, Q1l, Q1m, Q1n, Q1k′, Q1l′, Q1m′, Q1n′, Q3a, Q3b, Q3c, Q3d, Q3e, Q3f, Q3g and Q3h in Table 1 denote the following substituents).
71) The compounds wherein A, B, R1, L1, R2, L2, L3, Y, L4, R3 and X are any of the following combinations in Table 1, tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof (provided that in the case of 71), Q1a, Q1b, Q1c, Q1d, Q1e, Q1f, Q1g, Q1h, Q1i, Q1j, Q1k, Q1l, Q1m, Q1n, Q1k′, Q1l′, Q1m′, Q1n′, Q3a, Q3b, Q3c, Q3d, Q3e, Q3f, Q3g and Q3h in Table 1 denote the following substituents).
72) The compounds wherein A, B, R1, L1, R2, L2, L3, Y, L4, R3 and X are any of the following combinations in Table 1, tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof (provided that in the case of 72), Q1a, Q1b, Q1c, Q1d, Q1e, Q1f, Q1g, Q1h, Q1i, Q1j, Q1k, Q1l, Q1m, Q1n, Q1k′, Q1l′, Q1m′, Q1n′, Q3a, Q3b, Q3c, Q3d, Q3e, Q3f, Q3g and Q3h in Table 1 denote the following substituents).
73) The compounds wherein A, B, R1, L1, R2, L2, L3, Y, L4, R3 and X are any of the following combinations in Table 1, tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof (provided that in the case of 73), Q1a, Q1b, Q1c, Q1d, Q1e, Q1f, Q1g, Q1h, Q1i, Q1j, Q1k, Q1l, Q1m, Q1n, Q1k′, Q1l′, Q1m′, Q1n′, Q3a, Q3b, Q3c, Q3d, Q3e, Q3f, Q3g and Q3h in Table 1 denote the following substituents).
74) The compounds wherein A, B, R1, L1, R2, L2, L3, Y, L4, R3 and X are any of the following combinations in Table 1, tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof (provided that in the case of 74), Q1a, Q1b, Q1c, Q1d, Q1e, Q1f, Q1g, Q1h, Q1i, Q1j, Q1k, Q1l, Q1m, Q1n, Q1k′, Q1l′, Q1m′, Q1n′, Q3a, Q3b, Q3c, Q3d, Q3e, Q3f, Q3g and Q3h in Table 1 denote the following substituents).
75) The compounds wherein A, B, R1, L1, R2, L2, L3, Y, L4, R3 and X are any of the following combinations in Table 1, tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof (provided that in the case of 75), Q1a, Q1b, Q1c, Q1d, Q1e, Q1f, Q1g, Q1h, Q1i, Q1j, Q1k, Q1l, Q1m, Q1n, Q1k′, Q1l′, Q1m′, Q1n′, Q3a, Q3b, Q3c, Q3d, Q3e, Q3f, Q3g and Q3h in Table 1 denote the following substituents).
76) The compounds wherein A, B, R1, L1, R2, L2, L3, Y, L4, R3 and X are any of the following combinations in Table 1, tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof (provided that in the case of 76), Q1a, Q1b, Q1c, Q1d, Q1e, Q1f, Q1g, Q1h, Q1i, Q1j, Q1k, Q1l, Q1m, Q1n, Q1k′, Q1l′, Q1m′, Q1n′, Q3a, Q3b, Q3c, Q3d, Q3e, Q3f, Q3g and Q3h in Table 1 denote the following substituents).
77) The compounds wherein A, B, R1, L1, R2, L2, L3, Y, L4, R3 and X are any of the following combinations in Table 1, tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof (provided that in the case of 77), Q1a, Q1b, Q1c, Q1d, Q1e, Q1f, Q1g, Q1h, Q1i, Q1j, Q1k, Q1l, Q1m, Q1n, Q1k′, Q1l′, Q1m′, Q1n′, Q3a, Q3b, Q3c, Q3d, Q3e, Q3f, Q3g and Q3h in Table 1 denote the following substituents).
78) The compounds wherein A, B, R1, L1, R2, L2, L3, Y, L4, R3 and X are any of the following combinations in Table 1, tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof (provided that in the case of 78), Q1a, Q1b, Q1c, Q1d, Q1e, Q1f, Q1g, Q1h, Q1i, Q1j, Q1k, Q1l, Q1m, Q1n, Q1k′y Q1l′, Q1m′, Q1n′, Q3a, Q3b, Q3c, Q3d, Q3e, Q3f, Q3g and Q3h in Table 1 denote the following substituents).
79) The compounds wherein A, B, R1, L1, R2, L2, L3, Y, L4, R3 and X are any of the following combinations in Table 1, tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof (provided that in the case of 79), Q1a, Q1b, Q1c, Q1d, Q1e, Q1f, Q1g, Q1h, Q1i, Q1j, Q1k, Q1l, Q1m, Q1n, Q1k′, Q1l′, Q1m′, Q1n′, Q3a, Q3b, Q3c, Q3d, Q3e, Q3f, Q3g and Q3h in Table 1 denote the following substituents).
80) The compounds wherein A, B, R1, L1, R2, L2, L3, Y, L4, R3 and X are any of the following combinations in Table 1, tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof (provided that in the case of 80), Q1a, Q1b, Q1c, Q1d, Q1e, Q1f, Q1g, Q1h, Q1i, Q1j, Q1k, Q1l, Q1m, Q1n, Q1k′, Q1l′, Q1m′, Q1n′, Q3a, Q3b, Q3c, Q3d, Q3e, Q3f, Q3g and Q3h in Table 1 denote the following substituents).
81) The compounds wherein A, B, R1, L1, R2, L2, L3, Y, L4, R3 and X are any of the following combinations in Table 1, tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof (provided that in the case of 81), Q1a, Q1b, Q1c, Q1d, Q1e, Q1f, Q1g, Q1h, Q1i, Q1j, Q1k, Q1l, Q1m, Q1n, Q1k′, Q1l′, Q1m′, Q1n′, Q3a, Q3b, Q3c, Q3d, Q3e, Q3f, Q3g and Q3h in Table 1 denote the following substituents).
82) The compounds represented by any of 59) to 81) wherein X is converted to SH, tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
83) The compounds represented by any of 59) to 81) wherein X is converted to NH2, tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
84) The compounds represented by any of 59) to 81) wherein X is converted to OAc, tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof.
85) The thrombopoietin receptor activators represented by any of 1) to 84).
86) Preventive, therapeutic and improving agents for diseases against which activation of the thrombopoietin receptor is effective, which contain the thrombopoietin receptor activators represented by 85) or the formula (1), tautomers, prodrugs or pharmaceutically acceptable salts of the activators or solvates thereof, as an active ingredient.
87) Platelet increasing agents containing the thrombopoietin receptor activators represented by 85) or the formula (1), tautomers, prodrugs or pharmaceutically acceptable salts of the activators or solvates thereof, as an active ingredient.
88) Medicaments containing the compounds represented by any of 1) to 84) or the formula (1), tautomers, prodrugs or pharmaceutically acceptable salts of the compounds or solvates thereof, as an active ingredient.
In the present invention, the compounds of the present invention represented by the formula (1) may be present in the form of tautomers or geometrical isomers which undergo endocyclic or exocyclic isomerization, mixtures of tautomers or geometric isomers or mixtures of thereof. When the compounds of the present invention have an asymmetric center, whether or not resulting from an isomerization, the compounds of the present invention may be in the form of resolved optical isomers or in the form of mixtures containing them in certain ratios.
For example, furan compounds, thiophene compounds and pyrrole compounds of the present invention may be present in the form of tetronic acid (4-hydroxy-2(5H)-furanone) analogues, thiotetronic acid (4-hydroxy-2(5H)-thiophenone) analogues and tetraminic acid (4-hydroxy-3-pyrrolin-2-one) analogues as shown below by the formulae (2), (3) and (4), mixtures thereof or mixtures of isomers thereof.
The compounds of the present invention represented by the formula (1) or pharmaceutically acceptable salts thereof may be in the form of arbitrary crystals or arbitrary hydrates, depending on the production conditions. The present invention covers these crystals, hydrates and mixtures. They may be in the form of solvates with organic solvents such as acetone, ethanol and tetrahydrofuran, and the present invention covers any of these forms.
The compounds of the present invention represented by the formula (1) may be converted to pharmaceutically acceptable salts or may be liberated from the resulting salts, if necessary. The pharmaceutically acceptable salts of the present invention may be, for example, salts with alkali metals (such as lithium, sodium and potassium), alkaline earth metals (such as magnesium and calcium), ammonium, organic bases and amino acids. They may be salts with inorganic acids (such as hydrochloric acid, hydrobromic acid, phosphoric acid and sulfuric acid) and organic acids (such as acetic acid, citric acid, maleic acid, fumaric acid, benzenesulfonic acid and p-toluenesulfonic acid).
The compounds which serve as prodrugs are derivatives of the present invention having chemically or metabolically degradable groups which give pharmacologically active compounds of the present invention upon solvolysis or under physiological conditions in vivo. Methods for selecting or producing appropriate prodrugs are disclosed, for example, in Design of Prodrug (Elsevier, Amsterdam 1985). In the present invention, when the compound has a hydroxyl group, acyloxy derivatives obtained by reacting the compound with appropriate acyl halides or appropriate acid anhydrides may, for example, be mentioned as prodrugs. Acyloxys particularly preferred as prodrugs include —OCOC2H5, —OCO(t-Bu), —OCOC15H31, —OCO(m-CO2Na-Ph), —OCOCH2CH2CO2Na, —OCOCH(NH2)CH3, —OCOCH2N(CH3)2 and the like. When the compound of the present invention has an amino group, amide derivatives obtained by reacting the compound having an amino group with appropriate acid halides or appropriate mixed acid anhydrides may, for example, be mentioned as prodrugs. Amides particularly preferred as prodrugs include —NHCO(CH2)20OCH3, —NHCOCH(NH2)CH3 and the like. When the compound of the present invention has a carboxyl group, carboxylic acid esters with aliphatic alcohols or carboxylic acid esters obtained by the reaction with an alcoholic free hydroxyl group of 1,2- or 1,3-digylcerides may, for example, be mentioned as prodrugs. Particularly preferred prodrugs are methyl esters and ethyl esters.
The preventive, therapeutic and improving agents for diseases against which activation of the thrombopoietin receptor is effective or platelet increasing agents which contain the thrombopoietin receptor activators of the present invention, tautomers, prodrugs or pharmaceutically acceptable salts of the activators or solvates thereof as an active ingredient may usually be administered as oral medicines such as tablets, capsules, powder, granules, pills, and syrup, as rectal medicines, percutaneous medicines or injections. The agents of the present invention may be administered as a single therapeutic agent or as a mixture with other therapeutic agents. Though they may be administered as they are, they are usually administered in the form of medical compositions. These pharmaceutical preparations can be obtained by adding pharmacologically and pharmaceutically acceptable additives by conventional methods. Namely, for oral medicines, ordinary excipients, lubricants, binders, disintegrants, humectants, plasticizers and coating agents may be used. Oral liquid preparations may be in the form of aqueous or oily suspensions, solutions, emulsions, syrups or elixirs or may be supplied as dry syrups to be mixed with water or other appropriate solvents before use. Such liquid preparations may contain ordinary additives such as suspending agents, perfumes, diluents and emulsifiers. In the case of rectal administration, they may be administered as suppositories. Suppositories may use an appropriate substance such as cacao butter, laurin tallow, Macrogol, glycerogelatin, Witepsol, sodium stearate and mixtures thereof as the base and may, if necessary, contain an emulsifier, a suspending agent, a preservative and the like. For injections, pharmaceutical ingredients such as distilled water for injection, physiological saline, 5% glucose solution, propylene glycol and other solvents or solubilizing agents, a pH regulator, an isotonizing agent and a stabilizer may be used to form aqueous dosage forms or dosage forms which need dissolution before use.
The dose of the agents of the present invention for administration to human is usually about from 0.1 to 1000 mg/human/day in the case of oral drugs or rectal administration and about from 0.05 mg to 500 mg/human/day in the case of injections, though it depends on the age and conditions of the patient. The above-mentioned ranges are mere examples, and the dose should be determined from the conditions of the patient.
The present invention is used when the use of compounds which have thrombopoietin receptor affinity and act as thrombopoietin receptor agonists are expected to improve pathological conditions. For example, hematological disorders accompanied by abnormal platelet count may be mentioned. Specifically, it is effective for therapy or prevention of human and mammalian diseases caused by abnormal megakaryopoiesis, especially those accompanied by thrombocytopenia. Examples of such diseases include thrombocytopenia accompanying chemotherapy or radiotherapy of cancer, thrombocytopenia accompanying antiviral therapy for diseases such as hepatitis C, thrombocytopenia caused by bone marrow transplantation, surgery and serious infections, or gastrointestinal bleeding, but such diseases are not restricted to those mentioned. Typical thrombocytopenias such as aplastic anemia, idiopathic thrombocytopenic purpura, myelodysplastic syndrome, hepatic disease, HIV infection and thrombopoietin deficiency are also targets of the agents of the present invention. The present invention may be used as a peripheral stem cell mobilizer, a megakaryoblastic or megakaryocytic leukemia cell differentiation inducer and a platelet increasing agent for platelet donors. In addition, potential applications include therapeutic angiogenesis based on differentiation and proliferation of vascular endothelial cells and endothelial progenitor cells, prevention and therapy of arteriosclerosis, myocardial infarction, unstable angina, peripheral artery occlusive disease, but there is no restriction.
The compounds represented by the formula (1) are prepared by the process represented by the formula (5) illustrated below.
The reaction of the compound (I) with a —NH2 compound (II) in a solvent, if necessary in the presence of a catalyst, under heating with stirring gives a desired compound or its precursor. The precursor may be, if necessary, hydrolyzed, deprotected, reduced or oxidized to a desired compound. The compounds of the present invention usually can be purified by column chromatography, thin layer chromatography, high performance liquid chromatography (HPLC) or high performance liquid chromatography-mass spectrometry (LC-MS) and, if necessary, they may be obtained with high purity by recrystallization or washing with solvents.
For the syntheses of the intermediates (I), syntheses of the following heterocyclic compounds may be referred to.
For synthesis of the —NH2 compounds (II), for example, when L3=NH, the following may be referred to.
The compounds represented by the formula (1) wherein L3 is NR19, L4 is NH, and Y is O or S are prepared by the process represented by the formula (14) illustrated below.
The compounds represented by the formula (1) wherein L3 is NR19, L4 is a bond, and Y is O or S are prepared by the process represented by the formula (15) illustrated below.
The reaction of the compound (I) with a NH2 compound (IV) in a solvent, if necessary in the presence of a catalyst, under heating with stirring gives the compound (III) as the desired product.
The compounds represented by the formula (1) wherein L3 is NR19, L4 is NR22 or forms a heterocyclic group together with R3 are prepared by the process represented by the formula (16) illustrated below.
Now, the present invention will be described in further detail with reference to Reference Synthetic Examples, Synthetic Examples, Assay Examples and Formulation Examples. However, it should be understood that the present invention is by no means restricted by these specific Examples.
The 1H-NMR analysis was carried out at 300 MHz, and LC/MS was measured under the following conditions.
LC/MS Condition 1
Column: Waters SunFire C18 (3.5 μm, 4.6×30 mm)
Eluent: acetonitrile/0.1% aqueous formic acid (10/90→60/40)
LC/MS conditions 2
Column: Waters SunFire C18 (3.5 μm, 4.6×30 mm)
Eluent: acetonitrile/0.1% aqueous formic acid (10/90→85/15)
LC/MS Conditions 3
Column: Waters SunFire C18 (3.5 μm, 4.6×30 mm)
Eluent: acetonitrile/0.1% aqueous formic acid (20/80→100/0)
LC/MS Conditions 4
Column: Waters Xterra MSC18 (5 μm, 4.6×50 mm)
Eluent: acetonitrile/0.1% aqueous formic acid (10/90→60/40)
LC/MS Conditions 5
Column: Waters Xterra MSC18 (3.5 μm, 2.1×20 mm)
Eluent: acetonitrile/0.2% aqueous formic acid (20/80→90/10)
To a suspension of 2-(3,4-dichlorophenyl)-3-hydroxy-4-methylcarbonylthiophene (300 mg, 1.05 mmol) (prepared by the method disclosed in WO2004/108683) in isopropanol (20 mL) was added hydrazine monohydrate (61 μL, 1.25 mmol). The reaction mixture was refluxed for 1.5 hours, stirred at room temperature for 0.5 hour and at 0° C. for 1 hour. The precipitated solid was collected by filtration and dried by means of a vacuum pump to give the desired product (yield 100%).
Morphology: a pale yellow solid
1H-NMR (DMSO-d6) δ (ppm): 2.10 (s, 3H), 6.63 (br s, 2H), 7.58 (s, 2H), 7.61 (s, 1H), 7.98 (s, 1H), 12.88 (s, 1H).
LC/MS: condition 4, retention time 4.95 (min)
LC/MS (ESI+) m/z; 301, 303 [M+1]+
LC/MS (ESI−) m/z; 299, 301 [M−1]−
To a solution of methyl isonipecotate (1.0 g, 7.0 mmol) in tetrahydrofuran was added thiocarbonyl diimidazole (1.24 g, 6.98 mmol) at room temperature, and the reaction solution was stirred at room temperature for 1.5 hours and then stirred with hydrazine monohydrate (700 mg, 14.0 mmol) for 4 hours. After addition of saturated aqueous sodium chloride, the reaction solution was extracted with ethyl acetate and chloroform, and the extract was dried over anhydrous magnesium sulfate and concentrated to give the desired product (yield 114%).
Morphology: pale yellow solid
LC/MS: condition 5, retention time 0.52 (min)
LC/MS (ESI+) m/z; 218, [M+1]+
Synthesis was carried out in the same manner as in Reference Synthetic Example 2 by using ethyl nipecotate.
Synthesis was carried out in the same manner as in Reference Synthetic Example 2 by using isonipecotic acid diethylamide.
A solution of methyl hydrazinecarbothioate (1.0 g, 8.2 mmol) and piperidin-4-ol (1.24 g, 12.3 mmol) in ethanol (7 mL) was refluxed with heating at 90° C. for 2 days. After addition of ethyl acetate, the reaction solution was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated to give the crude desired product. The crude product was used directly for the next reaction.
Synthesis was carried out in the same manner as in Reference Synthetic Example 5 by using piperidin-3-ol.
Synthesis was carried out in the same manner as in Reference Synthetic Example 5 by using 4-piperidinemethanol.
A solution of 1-(tert-butoxycarbonyl)piperazine (1.38 g, 7.41 mmol) in acetonitrile (10 mL) was stirred with triethylamine (2.07 mL, 14.8 mmol) and methyl 2-bromoacetate (1.02 mL, 11.1 mmol) at room temperature for 4 hours and then filtered. The filtrate was concentrated, and after addition of saturated aqueous ammonium chloride, extracted with ethyl acetate. The organic phase was washed with saturated aqueous ammonium chloride and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated to give the desired product (yield 83%).
Morphology: pale yellow liquid
1H-NMR (CDCl3) δ: 1.46 (S, 9H), 2.53 (t, J=5.1 Hz, 4H), 3.24 (S, 2H), 3.49 (t, J=5.1 Hz, 4H), 3.73 (s, 3H)
Synthesis was carried out in the same manner as in Reference Synthetic Example 8 by using ethyl 3-bromopropionate.
Morphology: colorless mixture of solid and liquid
1H-NMR (CDCl3) δ: 1.26 (t, J=7.2 Hz, 3H), 1.46 (s, 9H), 2.41 (t, J=4.8 Hz, 4H), 2.50 (t, J=7.2 Hz, 2H), 2.71 (t, J=7.2 Hz, 2H), 3.42 (t, J=4.8 Hz, 4H), 4.14 (q, J=7.2 Hz, 2H)
A solution of methyl 2-[4-(tert-butoxycarbonyl)piperazin-1-yl]acetate prepared in Reference Synthetic Example 8 in dioxane (9 mL) was stirred with 4N hydrogen chloride/dioxane solution (3.91 mL, 15.7 mmol) at 80° C. for 1.5 hours. The solution was allowed to cool and filtered. Tetrahydrofuran and triethylamine (0.88 mL, 6.3 mmol) were added to the filter cake, and the procedure in Reference Synthetic Example 2 was followed using the resulting solution. The resulting crude product was used directly for the next reaction.
Morphology: pale yellow solid
Synthesis was carried out in the same manner as in Reference Synthetic Example 10 by using ethyl 3-[4-(tert-butoxycarbonyl)piperazin-1-yl]propionate prepared in Reference Synthetic Example 9.
Morphology: pale yellow solid
To a dimethylformamide solution (600 μL) of 2-(3,4-dichlorophenyl)-3-hydroxy-4-methylcarbonylthiophene (30 mg, 0.10 mmol) and methyl 1-hydrazinothiocarbonyl-piperidine-4-carboxylate (46 mg, 0.20 mmol) prepared in Reference Synthetic Example 2, concentrated hydrochloric acid (9 μL, 0.1 mmol) was added at room temperature, and the resulting solution was stirred at room temperature for 8 hours, then mixed with water and extracted with ethyl acetate. The extract was washed with 1 M hydrochloric acid and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1) and recrystallized from chloroform to give the desired product (yield 55%).
Morphology: white solid
1H-NMR (DMSO-d6) δ: 1.55-1.75 (m, 2H), 1.85-1.95 (m, 2H), 2.38 (s, 3H), 2.7-2.8 (m, 1H), 3.15-3.30 (m, 2H), 3.48 (s, 3H), 4.58 (d, J=13.5 Hz, 2H), 7.64 (d, J=8.4 Hz, 1H), 7.71 (d, J=8.4, 2.1 Hz, 1H), 8.00 (s, 1H), 8.03 (d, J=2.1 Hz, 1H), 12.4 (s, 1H)
LC/MS: condition 5, retention time 5.19 (min)
LC/MS (ESI+) m/z; 486, 488 [M+1]+
LC/MS (ESI−) m/z; 484, 486 [M−1]−
To a suspension of methyl 1-{1-[5-(3,4-dichlorophenyl)-4-hydroxythiophen-3-yl]-ethylidene-hydrazinocarbonyl}-piperidine-4-carboxylate (10 mg, 0.021 mmol) in methanol (300 μL), 1 M aqueous sodium hydroxide (250 μL) was added at room temperature, and the suspension was stirred at room temperature for 7 hours. After the reaction, 1 M hydrochloric acid (250 μL) was added, and the resulting crystals were collected by filtration as the desired product (yield 71%).
Morphology: gray solid
LC/MS: condition 5, retention time 4.87 (min)
LC/MS (ESI+) m/z; 472, 474 [M+1]+
LC/MS (ESI−) m/z; 470, 472 [M−1]−
A solution of 2-(3,4-dichlorophenyl)-4-(1-hydrazonoethyl)thiophen-3-ol (30 mg, 0.10 mmol) prepared in Reference Synthetic Example 1 and methyl 2-isothiocyanatoacetate (20 mg, 0.15 mmol) in dimethyl formamide (300 μL) was stirred at room temperature, 40° C. and 50° C. for 2 hours, respectively. After addition of methanol-water, the solution was stirred at room temperature for 0.5 hour, and the resulting crystals were collected by filtration as the desired product (yield 0.72%).
Morphology: white solid
LC/MS: condition 5, retention time 4.95 (min)
LC/MS (ESI+) m/z; 432, 434 [M+1]+
LC/MS (ESI−) m/z; 430, 432 [M−1]−
Synthesis was carried out in the same manner as in Synthetic Example 2 using methyl 2-[(2-{1-[5-(3,4-dichlorophenyl)-4-hydroxythiophen-3-yl]-ethylidene}-hydrazinocarbonothioyl)amino]acetate prepared in Synthetic Example 3 (yield 39%).
Morphology: white solid
LC/MS: condition 5, retention time 4.65 (min)
LC/MS (ESI+) m/z; 418, 420 [M+1]+
LC/MS (ESI−) m/z; 416, 418 [M−1]−
Synthesis was carried out in the same manner as in Synthetic Example 3 by using methyl 3-isothiocyanatopropionate (yield 78%).
Morphology: white solid
LC/MS: condition 5, retention time 5.03 (min)
LC/MS (ESI+) m/z; 446 [M+1]+
LC/MS (ESI−) m/z; 444, 446 [M−1]−
Synthesis was carried out in the same manner as in Synthetic Example 2 by using methyl 3-[(2-{1-[5-(3,4-dichlorophenyl)-4-hydroxythiophen-3-yl]-ethylidene}-hydrazinocarbonothioyl)amino]propionate prepared in Synthetic Example 5 (yield 41%).
Morphology: white solid
LC/MS: condition 5, retention time 4.74 (min)
LC/MS (ESI+) m/z; 432, 434 [M+1]+
LC/MS (ESI−) m/z; 430, 432 [M−1]−
Synthesis was carried out in the same manner as in Synthetic Example 3 by using 2-methoxyethyl isothiocyanate (yield 43%).
Morphology: pale yellow solid
LC/MS: condition 5, retention time 5.05 (min)
LC/MS (ESI+) m/z; 418, 420 [M+1]+
LC/MS (ESI−) m/z; 416, 418 [M−1]−
Synthesis was carried out in the same manner as in Synthetic Example 1 by using 1-[5-(4-bromophenyl)-4-hydroxy-thiophen-3-yl]-ethanone (prepared by the method disclosed in WO2004/108683) and methyl 1-hydrazinothiocarbonyl-piperidine-4-carboxylate prepared in Reference Synthetic Example 2 (yield 64%).
Morphology: pale yellow solid
LC/MS: condition 2, retention time 3.74 (min)
LC/MS (ESI+) m/z; 496, 498 [M+1]+
LC/MS (ESI−) m/z; 494, 496 [M−1]−
Synthesis was carried out in the same manner as in Synthetic Example 2 by using methyl 1-{1-[5-(4-bromophenyl)-4-hydroxy-thiophen-3-yl]-ethylidene-hydrazinothiocarbonyl}-piperidine-4-carboxylate prepared in Synthetic Example 8 (yield 87%).
Morphology: pale yellow solid
LC/MS: condition 2, retention time 3.45 (min)
LC/MS (ESI+) m/z; 482, 484 [M+1]+
LC/MS (ESI−) m/z; 480, 482 [M−1]−
Synthesis was carried out in the same manner as in Synthetic Example 1 using 1-[4-hydroxy-5-(4-trifluoromethylphenyl)-thiophen-3-yl]ethanone (prepared by the method disclosed in WO2004/108683) and methyl 1-hydrazinothiocarbonylpiperidine-4-carboxylate prepared in Reference Synthetic Example 2 (yield 36%).
Morphology: pale yellow solid
LC/MS: condition 1, retention time 4.54 (min)
LC/MS (ESI+) m/z; 486 [M+1]+
LC/MS (ESI−) m/z; 484 [M−1]−
Synthesis was carried out in the same manner as in Synthetic Example 2 using methyl 1-{1-[4-hydroxy-5-(4-trifluoromethylphenyl)-thiophen-3-yl]-ethylidene-hydrazinothiocarbonyl}-piperidine-4-carboxylate prepared above (yield 58%).
Morphology: white solid
LC/MS: condition 5, retention, time 4.88 (min)
LC/MS (ESI+) m/z; 472 [M+1]+
LC/MS (ESI−) m/z; 470 [M−1]−
Synthesis was carried out in the same manner as in Synthetic Example 1 using 1-[5-(4-trifluoromethoxyphenyl)-4-hydroxythiophen-3-yl]ethanone (prepared by the method disclosed in WO2004/108683) and methyl 1-hydrazinothiocarbonylpiperidine-4-carboxylate prepared in Reference Synthetic Example 2 (yield 53%).
Morphology: pale yellow solid
LC/MS: condition 2, retention time 3.75 (min)
LC/MS (ESI+) m/z; 502 [M+1]+
LC/MS (ESI−) m/z; 500 [M−1]−
Synthesis was carried out in the same manner as in Synthetic Example 2 using methyl 1-{1-[5-(4-trifluoromethoxyphenyl)-4-hydroxythiophen-3-yl]-ethylidene-hydrazinothiocarbonyl}-piperidine-4-carboxylate prepared above (yield 52%).
Morphology: pale yellow solid
LC/MS: condition 2, retention time 3.49 (min)
LC/MS (ESI+) m/z; 488 [M+1]+
LC/MS (ESI−) m/z; 486 [M−1]−
Synthesis was carried out in the same manner as in Synthetic Example 1 using 1-[5-(4-chlorophenyl)-4-hydroxy-thiophen-3-yl]ethanone (prepared by the method disclosed in WO2004/108683) and methyl 1-hydrazinothiocarbonylpiperidine-4-carboxylate prepared in Reference Synthetic Example 2 (yield 41%).
Morphology: pale yellow solid
LC/MS: condition 1, retention time 4.50 (min)
LC/MS (ESI+) m/z; 452, 454 [M+1]+
LC/MS (ESI−) m/z; 450, 452 [M−1]−
Synthesis was carried out in the same manner as in Synthetic Example 2 using methyl 1-{1-[5-(4-chlorophenyl)-4-hydroxy-thiophen-3-yl]-ethilidene-hydrazinothiocarbonyl}-piperidine-4-carboxylate prepared above (yield 92%).
Morphology: yellow solid
LC/MS: condition 1, retention time 4.14 (min)
LC/MS (ESI+) m/z; 438, 440 [M+1]+
LC/MS (ESI−) m/z; 436, 438 [M−1]−
Synthesis was carried out in the same manner as in Synthetic Example 1 using 1-[5-(3,4-dimethylphenyl)-4-hydroxy-thiophen-3-yl]-ethanone (prepared by the method disclosed in WO2004/108683) and methyl 1-hydrazinothiocarbonylpiperidine-4-carboxylate prepared in Reference Synthetic Example 2 (yield 28%).
Morphology: pale yellow solid
LC/MS: condition 2, retention time 3.69 (min)
LC/MS (ESI+) m/z; 446 [M+1]+
LC/MS (ESI−) m/z; 444 [M−1]−
Synthesis was carried out in the same manner as in Synthetic Example 2 using methyl 1-{1-[5-(3,4-dimethylphenyl)-4-hydroxy-thiophen-3-yl]-ethylidene-hydrazinothiocarbonyl}-piperidine-4-carboxylate prepared above (yield 100%).
Morphology: pale brown solid
LC/MS: condition 2, retention time 3.38 (min)
LC/MS (ESI+) m/z; 431.78 [M+1]+
LC/MS (ESI−) m/z; 429.89 [M−1]−
Synthesis was carried out in the same manner as in Synthetic Example 1 using 2-(4-t-butylphenyl)-3-hydroxy-4-methylcarbonylthiophene and methyl 1-hydrazinothiocarbonylpiperidine-4-carboxylate prepared in Reference Synthetic Example 2 (yield 57%).
Morphology: pale brown solid
LC/MS: condition 2, retention time 3.87 (min)
LC/MS (ESI+) m/z; 474 [M+1]+
LC/MS (ESI−) m/z; 472 [M−1]−
Synthesis was carried out in the same manner as in Synthetic Example 2 using methyl 1-{1-[5-(4-t-butylphenyl)-4-hydroxy-thiophen-3-yl]-ethylidene-hydrazinothiocarbonyl}-piperidine-4-carboxylate prepared above (yield 89%).
Morphology: dark brown solid
1H-NMR (ppm in DMSO-d6)
δ 1.22 (s, 9H), 1.57-1.61 (m, 2H), 1.88-1.92 (m, 2H), 2.36 (s, 3H), 4.53-4.58 (m, 2H), 7-41 (d, 2H, J=8.5 Hz), 7.67 (d, 2H, J=8.5 Hz), 7.85 (s, 1H), 10.25 (brs, 1H), 11.98 (brs, 1H)
Synthesis was carried out in the same manner as in Synthetic Example 1 using 1-[5-(3-chlorophenyl)-4-hydroxythiopen-3-yl]ethanone (prepared by the method disclosed in WO2004/108683) and methyl 1-hydrazinothiocarbonylpiperidine-4-carboxylate prepared in Reference Synthetic Example 2 (yield 63%).
Morphology: pale yellow solid
LC/MS: condition 2, retention time 3.67 (min)
LC/MS (ESI+) m/z; 452, 454 [M+1]+
LC/MS (ESI−) m/z; 450, 452 [M−1]−
Synthesis was carried out in the same manner as in Synthetic Example 2 using methyl 1-{1-[5-(3-chlorophenyl)-4-hydroxythiophen-3-yl]-ethylidene-hydrazinothiocarbonyl}-piperidine-4-carboxylate prepared above (yield 71%).
Morphology: pale yellow solid
LC/MS: condition 2, retention time 3.38 (min)
LC/MS (ESI+) m/z; 438, 440 [M+1]+
LC/MS (ESI−) m/z; 436, 438 [M−1]−
Synthesis was carried out in the same manner as in Synthetic Example 1 using 1-[4-hydroxy-1-methyl-5-(4-trifluoromethylphenyl)-1H-pyrazol-3-yl]ethanone (prepared by the method disclosed in WO2004/108683) and methyl 1-hydrazinothiocarbonylpiperidine-4-carboxylate prepared in Reference Synthetic Example 2 (yield 70%).
Morphology: yellow solid
LC/MS: condition 1, retention time 4.12 (min)
LC/MS (ESI+) m/z; 484 [M+1]+
LC/MS (ESI−) m/z; 482 [M−1]−
Synthesis was carried out in the same manner as in Synthetic Example 2 using methyl 1-{1-[4-hydroxy-1-methyl-5-(4-trifluoromethylphenyl)-1H-pyrazol-3-yl]-ethylidene-hydrazinothiocarbonyl}-piperidine-4-carboxylate prepared above (yield 85%).
Morphology: pale yellow solid
LC/MS: condition 1, retention time 3.69 (min)
LC/MS (ESI+) m/z; 470 [M+1]+
LC/MS (ESI−) m/z; 468 [M−1]−
Synthesis was carried out in the same manner as in Synthetic Example 1 using 1-[5-(3,4-dichlorophenyl)-4-hydroxy-1-methyl-1H-pyrazol-3-yl]ethanone (prepared by the method disclosed in WO2004/108683) and methyl 1-hydrazinothiocarbonylpiperidine-4-carboxylate prepared in Reference Synthetic Example 2 (yield 61%).
Morphology: pale pink solid
LC/MS: condition 1, retention time 4.30 (min)
LC/MS (ESI+) m/z; 484, 486 [M+1]+LC/MS (ESI−) m/z; 482, 484 [M−1]−
Synthesis was carried out in the same manner as in Synthetic Example 2 using methyl 1-{1-[5-(3,4-dichlorophenyl)-4-hydroxy-1-methyl-1H-pyrazol-3-yl]-ethylidene-hydrazinothiocarbonyl}-piperidine-4-carboxylate prepared above (yield 89%).
Morphology: pale yellow solid
LC/MS: condition 1, retention time 3.79 (min)
LC/MS (ESI+) m/z; 470, 472 [M+1]+
LC/MS (ESI−) m/z; 468, 470 [M−1]−
Synthesis was carried out in the same manner as in Synthetic Example 1 using ethyl 1-hydrazionothiocarbonylpiperidine-3-carboxylate prepared in Reference Synthetic Example 3 (yield 52%).
Morphology: white solid
Synthesis was carried out in the same manner as in Synthetic Example 2 using ethyl 1-{1-[5-(3,4-dichlorophenyl)-4-hydroxythiophen-3-yl]-ethylidene-hydrazinothiocarbonyl}-piperidine-3-carboxylate prepared above (yield 67%).
Morphology: white solid
LC/MS: condition 5, retention time 4.98 (min)
LC/MS (ESI+) m/z; 472 [M+1]+
LC/MS (ESI−) m/z; 470 [M−1]−
Synthesis was carried out in the same manner as in Synthetic Example 1 using 1-hydrazionothiocarbonylpiperidine-4-carboxylic acid diethylamide prepared in Reference Synthetic Example 4 (yield 23%).
Morphology: white solid
LC/MS: condition 5, retention time 3.80 (min)
LC/MS (ESI+) m/z; 527 [M+1]+
Synthesis was carried out in the same manner as in Synthetic Example 1 using 1-hydrazinothiocarbonylpiperidin-4-ol prepared in Reference Synthetic Example 5 (yield 21%).
Morphology: white solid
LC/MS: condition 5, retention time 4.88 (min)
LC/MS (ESI+) m/z; 444 [M+1]+
LC/MS (ESI−) m/z; 442 [M−1]−
Synthesis was carried out in the same manner as in Synthetic Example 1 using crude 1-hydrazinothiocarbonylpiperidin-3-ol prepared in Reference Synthetic Example 6 (yield 53%).
Morphology: pale yellow solid
LC/MS: condition 5, retention time 4.92 (min)
LC/MS (ESI+) m/z; 444 [M+1]+
LC/MS (ESI−) m/z; 442 [M−1]−
Synthesis was carried out in the same manner as in Synthetic Example 1 using crude 1-hydrazinothiocarbonylpiperidine-4-methanol prepared in Reference Synthetic Example 7 (yield 22%).
Morphology: white solid
LC/MS: condition 5, retention time 4.98 (min)
LC/MS (ESI+) m/z; 458 [M+1]+
LC/MS (ESI−) m/z; 456 [M−1]−
Synthesis was carried out in the same manner as in Synthetic Example 3 using 3-methoxypropyl isothiocyanate (yield 19%).
Morphology: pale yellow solid
LC/MS: condition 5, retention time 5.22 (min)
LC/MS (ESI+) m/z; 432 [M+1]+
LC/MS (ESI−) m/z; 430 [M−1]−
To 1-{1-[5-(4-bromophenyl)-4-hydroxythiophen-3-yl]-ethylidene-hydrazinothiocarbonyl}-piperidine-4-carboxylic acid (84 mg, 0.17 mmol) prepared in Synthetic Example 9, dimethylformamide (2 mL) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (66 mg, 0.25 mmol) and HOBt (47 mg, 0.25 mmol) were added, and then dimethylformamide (2.5 mL) and diisopropylethylamine (91 μl, 0.52 mmol) were added. The resulting solution was stirred at room temperature for 1 hour and then stirred with a dimethylformamide solution (1.5 mL) of 4-picolylamine (47 mg, 0.43 mmol) for 24 hours. After addition of water, the reaction mixture was filtered, and the filter cake was dried and washed with isopropyl alcohol repeatedly to give the desired product (yield 34%).
Morphology: pale yellow solid
LC/MS: condition 1, retention time 3.05 (min)
LC/MS (ESI+) m/z; 572, 574 [M+1]+
LC/MS (ESI−) m/z; 570, 572 [M−1]−
Synthesis was carried out in the same manner as in Synthetic Example 24 using 2-picolylamine (yield 22%).
Morphology: pale yellow solid
LC/MS: condition 1, retention time 3.62 (min)
LC/MS (ESI+) m/z; 572, 574 [M+1]+
LC/MS (ESI−) m/z; 570, 572 [M−1]−
Synthesis was carried out in the same manner as in Synthetic Example 24 using 3-picolylamine (yield 4%).
Morphology: yellow solid
LC/MS: condition 1, retention time 3.25 (min)
LC/MS (ESI+) m/z; 572, 574 [M+1]+
LC/MS (ESI−) m/z; 570, 572 [M−1]−
Methyl 2-[4-hydrazinothiocarbonylpiperazin-1-yl]acetate (356 mg, 1.52 mmol) prepared in Reference Synthetic Example 10 and 2-(3,4-dichlorophenyl)-3-hydroxy-4-methylcarbonylthiophene (147 mg, 0.512 mmol) were stirred with dimethylformamide (4 mL) and concentrated hydrochloric acid (42.6 μL, 1.52 mmol) at room temperature to 60° C. for 5 days. After addition of water, the reaction mixture was filtered, and the filter cake was dried. The filter cake was mixed with chloroform and filtered, and the filtrate was concentrated then mixed with chloroform, isopropyl alcohol and n-hexane and filtered. The filter cake was dried to give the crude desired product (yield 18%). The crude product was used directly for the next reaction.
LC/MS: condition 1, retention time 3.97 (min)
LC/MS (ESI+) m/z; 501, 503 [M+1]+
LC/MS (ESI+ m/z; 499, 501 [M−1]−
The procedure in Synthetic Example 2 was followed using methyl 2-[4-{1-[5-(3,4-dichlorophenyl)-4-hydroxythiophen-3-yl]-ethylidene-hydrazinothiocarbonyl}-piperazin-1-yl]acetate to give the crude desired product. The crude product was washed with chloroform to give the desired product (yield 11%).
Morphology: pale yellow solid
LC/MS: condition 1, retention time 3.60 (min)
LC/MS (ESI+) m/z; 487, 489 [M+1]+
LC/MS (ESI−) m/z; 485, 487 [M−1]−
The condensation procedure in Synthetic Example 27 was followed using 2-(4-bromophenyl)-3-hydroxy-4-methylcarbonylthiophene to give the crude desired product (yield 57%). The crude product was used directly for the next reaction.
Morphology: pale yellow solid
The hydrolysis procedure in Synthetic Example 27 was followed using methyl 2-[4-{1-[5-(4-bromophenyl)-4-hydroxythiophen-3-yl]-ethylidene-hydrazinothiocarbonyl}-piperazin-1-yl]acetate to give the desired product (yield 43%).
Morphology: pale yellow solid
LC/MS: condition 1, retention time 3.45 (min)
LC/MS (ESI+) m/z; 497, 499 [M+1]+.
LC/MS (ESI−) m/z; 495, 497 [M−1]−
The condensation procedure in Synthetic Example 27 was followed using ethyl 3-[4-hydrazinothiocarbonylpiperazin-1-yl]propionate prepared in Reference Synthetic Example 11 to give the crude desired product (yield 13%). The crude product was used directly for the next reaction.
LC/MS: condition 1, retention time 3.05 (min)
LC/MS (ESI+) m/z; 539, 541 [M+1]+
LC/MS (ESI−) m/z; 537, 539 [M−1]−
The hydrolysis procedure in Synthetic Example 2 was followed using methyl 3-[4-{1-[5-(4-bromophenyl)-4-hydroxythiophen-3-yl]-ethylidene-hydrazinothiocarbonyl}-piperazin-1-yl]propionate and ethanol as the solvent to give the desired product (yield 55%).
Morphology: pale yellow solid
LC/MS: condition 1, retention time 3.07 (min)
LC/MS (ESI+) m/z; 511, 513 [M+1]+
LC/MS (ESI−) m/z; 509, 511 [M−1]−
The structural formulae of the compounds obtained in the Synthetic Examples are given below.
The reactivity of the compound of Synthetic Example 4 of the present invention with thrombopoietin (TPO) receptor was assayed using a human leukemic cell line, UT7/EPO-mpl.
(1) Cells and Cell Culture
UT7/EPO-mpl is a stable transformed cell line obtained by introducing into human leukemic cell line UT7/EPO a vector that induces expression of human TPO receptor (c-mp1) under control of cytomegalovirus immediate-early promoter by the method of Takatoku et al. (J. Biol. Chem., 272:7259-7263 (1997)). Proliferation of this cell line is stimulated by TPO, while its mother cell line UT7/EPO exhibits no response to TPO. These two cell lines were subcultured in Iscove's modified Dulbecco's medium (IMDM; GIBCO) containing 10% fetal bovine serum (FBS; Thermo Electron or BioWest) using a CO2 incubator (5% CO2, 37° C.).
(2) Cell Proliferation Assay
The subcultured cells described above were washed twice with phosphate buffered saline (PBS) and suspended in IMDM containing 10% FBS at a cell density of 6×104 cells/ml. The cell suspension was transferred to a 96-well tissue culture plate (CORNING) in 100-μl aliquots. Then either TPO (Pepro Tech EC) or the compound of Synthetic Example 4 dissolved in dimethyl sulfoxide (DMSO) was diluted 83-fold with IMDM containing 10% FBS and added to the aforementioned cell suspension in 20-μl aliquots. The cell suspension was incubated in a CO2 incubator (5% CO2, 37° C.) for 4 days. Cell proliferation was assayed using WST-8 reagent (Kishida Chemical Co., Ltd.) according to instructions by the manufacturer. A 10-μl aliquot of 5 mM WST-8 reagent solution was added to each well of the tissue culture plate, and the plate was incubated at 37° C. for 4 h. The formazan pigment generated was detected by measuring the absorbance at 450 nm with a 96-well microplate reader (Nihon Molecular Devices, Spectramax 190).
The compounds of the following Synthetic Examples were tested according to the method of Assay Example 1 to determine the concentration of each compound that yields a growth rate corresponding to 50% of the growth of human leukemic cell line UT-7/EPO-mpl observed in the presence of 10 ng/ml TPO (EC50). The results are summarized in Table 4.
A granule preparation containing the following ingredients is prepared.
A compound represented by the formula (1) and lactose are sifted through a 60-mesh sieve. Corn starch is sifted though a 120-mesh sieve. They are mixed in a V-type blender. The powder mixture is kneaded with a low-viscosity hydroxypropylcellulose (HPC-L) aqueous solution, granulated (extrusion granulation, die size 0.5-1 mm) and dried. The resulting dry granules are sifted through a shaking sieve (12/60 mesh) to obtain a granule preparation.
A powder preparation for capsulation containing the following ingredients is prepared.
A compound represented by the formula (1) and lactose are sifted through a 60-mesh sieve. Corn starch is sifted though a 120-mesh sieve. They are mixed with magnesium stearate in a V-type blender. The 10% powder is put in hard gelatin capsules No. 5, 100 mg each.
A granule preparation for capsulation containing the following ingredients is prepared.
A compound represented by the formula (1) and lactose are sifted through a 60-mesh sieve. Corn starch is sifted though a 120-mesh sieve. They are mixed in a V-type blender. The powder mixture is kneaded with a low-viscosity hydroxypropylcellulose (HPC-L) aqueous solution, granulated and dried. The resulting dry granules are sifted through a shaking sieve (12/60 mesh). The granules are put in hard capsules No. 4, 150 mg each.
A tablet preparation containing the following ingredients is prepared.
A compound represented by the formula (1), lactose, microcrystalline cellulose and CMC-Na (carboxymethylcellulose sodium salt) are sifted through a 60-mesh sieve and mixed. The powder mixture is mixed with magnesium stearate to give a bulk powder mixture. The powder mixture is compressed directly into 150 mg tablets.
An intravenous preparation is prepared as follows.
Solutions having the above-mentioned composition are usually administered to a patient intravenously at a rate of 1 ml per 1 minute.
The compounds of the present invention which have affinity for thrombopoietin receptor and act as thrombopoietin receptor agonists are useful as preventive, therapeutic and improving agents for diseases against which activation of the thrombopoietin receptor is effective, especially as drugs for hematological disorders accompanied by abnormal platelet count and as drugs for diseases treated or prevented by stimulating differentiation and proliferation of vascular endothelial cells and endothelial progenitor cells, and are useful as medicines.
| Number | Date | Country | Kind |
|---|---|---|---|
| 2004-355195 | Dec 2004 | JP | national |
| 2005-330891 | Nov 2005 | JP | national |
| Filing Document | Filing Date | Country | Kind | 371c Date |
|---|---|---|---|---|
| PCT/JP2005/022907 | 12/7/2005 | WO | 00 | 6/8/2007 |
| Publishing Document | Publishing Date | Country | Kind |
|---|---|---|---|
| WO2006/062240 | 6/15/2006 | WO | A |
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