US 7,351,841 B2
Heterocyclic compounds and thrombopoietin receptor activators
Shingo Owada, Funabashi (Japan); Shunsuke Iwamoto, Funabashi (Japan); Kazufumi Yanagihara, Funabashi (Japan); Katsuaki Miyaji, Funabashi (Japan); Takanori Nakamura, Minami-saitama-gun (Japan); Norihisa Ishiwata, Minami-saitama-gun (Japan); and Yutaka Hirokawa, Funabashi (Japan)
Assigned to Nissan Chemical Industries, Ltd., Tokyo (Japan)
Filed on Dec. 06, 2005, as Appl. No. 11/294,609.
Application 11/294609 is a continuation in part of application No. PCT/JP04/08165, filed on Jun. 04, 2004.
Claims priority of application No. 2003-161987 (JP), filed on Jun. 06, 2003; application No. 2003-330627 (JP), filed on Sep. 22, 2003; application No. 2003-404635 (JP), filed on Dec. 03, 2003; and application No. 2004-094931 (JP), filed on Mar. 29, 2004.
Prior Publication US 2006/0094694 A1, May 04, 2006
Int. Cl. C07D 333/12 (2006.01); C07D 333/16 (2006.01); C07D 333/18 (2006.01); C07D 333/20 (2006.01); C07D 333/32 (2006.01); C07D 333/34 (2006.01); A61K 31/381 (2006.01)
U.S. Cl. 549—62  [549/68; 549/70; 549/74; 549/78; 549/80; 514/445; 514/446; 514/447; 514/448] 111 Claims
 
1. A compound represented by the formula (1)

OG Complex Work Unit Drawing
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 alkylcarbonyloxy 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 alkylcarbonyloxy 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: a carboxyl group, a nitro group, a cyano group, a halogen atom, a C1-10 alkoxy group, a C1-10 alkylcarbonyl group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonylamino group, an amino group, a mono- or di-C1-10 alkylamino group, a hydroxyl group, a protected hydroxyl group, a C2-14 aryl group and 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 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: a C1-10 alkyl group (the C1-10 alkyl group may be substituted with one or more halogen atoms), a C2-6 alkenyl group, a C2-6 alkynyl group, a carboxyl group, a nitro group, a cyano group, a halogen atom, a C1-10 alkoxy group, a C1-10 alkylcarbonyl group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonylamino group, an amino group, a mono- or di-C1-10 alkylamino group, a hydroxyl group, a protected hydroxyl group, a C2-14 aryl group and a C2-14 aryloxy group), 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: a C1-10 alkyl group (the C1-10 alkyl group may be substituted with one or more halogen atoms), a C2-6 alkenyl group, a C2-6 alkynyl group, a carboxyl group, a nitro group, a cyano group, a halogen atom, a C1-10 alkoxy group, a C1-10 alkylcarbonyl group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonylamino group, an amino group, a mono- or di-C1-10 alkylamino group, a hydroxyl group, a protected hydroxyl group, a C2-14 aryl group and a C2-14 aryloxy group), 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: a carboxyl group, a nitro group, a cyano group, a halogen atom, a C1-10 alkoxy group, a C1-10 alkylcarbonyl group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonylamino group, an amino group, a mono- or di-C1-10 alkylamino group, a hydroxyl group, a protected hydroxyl group, a C2-14 aryl group and 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 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: a C1-10 alkyl group (the C1-10 alkyl group may be substituted with one or more halogen atoms), a C2-6 alkenyl group, a C2-6 alkynyl group, a carboxyl group, a nitro group, a cyano group, a halogen atom, a C1-10 alkoxy group, a C1-10 alkylcarbonyl group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonylamino group, an amino group, a mono- or di-C1-10 alkylamino group, a hydroxyl group, a protected hydroxyl group, a C2-14 aryl group and a C2-14 aryloxy group), 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: a C1-10 alkyl group (the C1-10 alkyl group may be substituted with one or more halogen atoms), a C2-6 alkenyl group, a C2-6 alkynyl group, a carboxyl group, a nitro group, a cyano group, a halogen atom, a C1-10 alkoxy group, a C1-10 alkylcarbonyl group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonylamino group, an amino group, a mono- or di-C1-10 alkylamino group, a hydroxyl group, a protected hydroxyl group, a C2-14 aryl group and a C2-14 aryloxy group) 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 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: a carboxyl group, a nitro group, a cyano group, a halogen atom, a C1-10 alkoxy group, a C1-10 alkylcarbonyl group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonylamino group, an amino group, a mono- or di-C1-10 alkylamino group, a hydroxyl group, a protected hydroxyl group, a C2-14 aryl group and 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 group 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: a C1-10 alkyl group (the C1-10 alkyl group may be substituted with one or more halogen atoms), a C2-6 alkenyl group, a C2-6 alkynyl group, a carboxyl group, a nitro group, a cyano group, a halogen atom, a C1-10 alkoxy group, a C1-10 alkylcarbonyl group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonylamino group, an amino group, a mono- or di-C1-10 alkylamino group, a hydroxyl group, a protected hydroxyl group, a C2-14 aryl group and a C2-14 aryloxy group), 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: a carboxyl group, a nitro group, a cyano group, a halogen atom, a C1-10 alkoxy group, a C1-10 alkylcarbonyl group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonylamino group, an amino group, a mono- or di-C1-10 alkylamino group, a hydroxyl group, a protected hydroxyl group, a C2-14 aryl group and a C2-14 aryloxy group (the C2-14 aryl group and the C2-14 aryloxy group may be substituted with one or more C2-6 alkyl groups (the C1-6 alkyl group 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: a C1-10 alkyl group (the C1-10 alkyl group may be substituted with one or more halogen atoms), a C2-6 alkenyl group, a C2-6 alkynyl group, a carboxyl group, a nitro group, a cyano group, a halogen atom, a C1-10 alkoxy group, a C1-10 alkylcarbonyl group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonylamino group, an amino group, a mono- or di-C1-10 alkylamino group, a hydroxyl group, a protected hydroxyl group, a C2-14 aryl group and a C2-14 aryloxy group)), and each of m1 and m2 is independently an integer of from 0 to 5 provided that m1m2 is 3, 4 or 5)))),
B is a sulfur atom,
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: a halogen atom, a carboxyl group, a nitro group, OCHO, a cyano group, a hydroxyl group, a protected hydroxyl 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, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkoxy group, the C1-10 alkylcarbonyl group, the C1-10 alkylcarbonyloxy group and the C1-10 alkoxycarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of: a carboxyl group, a nitro group, a cyano group, a halogen atom, a C1-10 alkoxy group, a C1-10 alkylcarbonyl group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonylamino group, an amino group, a mono- or di-C1-10 alkylamino group, a hydroxyl group, a protected hydroxyl group, a C2-14 aryl group and 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 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: a C1-10 alkyl group (the C1-10 alkyl group may be substituted with one or more halogen atoms), a C2-6 alkenyl group, a C2-6 alkynyl group, a carboxyl group, a nitro group, a cyano group, a halogen atom, a C1-10 alkoxy group, a C1-10 alkylcarbonyl group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonylamino group, an amino group, a mono- or di-C1-10 alkylamino group, a hydroxyl group, a protected hydroxyl group, a c2-14 aryl group and a C2-14 aryloxy group), a thiol group and an amino group (the thiol group and the amino group may be optionally substituted with one or two substituents selected from the group consisting of: a formyl group, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group and 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: a carboxyl group, a nitro group, a cyano group, a halogen atom, a C1-10 alkoxy group, a C1-10 alkylcarbonyl group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonylamino group, an amino group, a mono- or di-C1-10 alkylamino group, a hydroxyl group, a protected hydroxyl group, a C2-14 aryl group and 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 group may be substituted with one or more halogen atoms) or one or more halogen atoms)))),
L1 is a bond, CR10R11 (where in 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: a carboxyl group, a nitro group, a cyano group, a halogen atom, a C1-10 alkoxy group, a C1-10 alkylcarbonyl group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonylamino group, an amino group, a mono- or di-C1-10 alkylamino group, a hydroxyl group, a protected hydroxyl group, a C2-14 aryl group and 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 group 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: a C1-10 alkyl group (the C1-10 alkyl group may be substituted with one or more halogen atoms), a C2-6 alkenyl group, a C2-6 alkynyl group, a carboxyl group, a nitro group, a cyano group, a halogen atom, a C1-10 alkoxy group, a C1-10 alkylcarbonyl group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonylamino group, an amino group, a mono- or di-C1-10 alkylamino group, a hydroxyl group, a protected hydroxyl group, a C2-14 aryl group and a C2-14 aryloxy group)),
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: a carboxyl group, a nitro group, a cyano group, a halogen atom, a C1-10 alkoxy group, a C1-10 alkylcarbonyl group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonylamino group, an amino group, a mono- or di-C1-10 alkylamino group, a hydroxyl group, a protected hydroxyl group, a C2-14 aryl group and 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 group 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: a carboxyl group, a nitro group, a cyano group, a halogen atom, a C1-10 alkoxy group, a C1-10 alkylcarbonyl group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonylamino group, an amino group, a mono- or di-C1-10 alkylamino group, a hydroxyl group, a protected hydroxyl group, a C2-14 aryl group and 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 group 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: a C1-10 alkyl group (the C1-10 alkyl group may be substituted with one or more halogen atoms), a C2-6 alkenyl group, a C2-6 alkynyl group, a carboxyl group, a nitro group, a cyano group, a halogen atom, a C1-10 alkoxy group, a C1-10 alkylcarbonyl group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonylamino group, an amino group, a mono- or di-C1-10 alkylamino group, a hydroxyl group, a protected hydroxyl group, a C2-14 aryl group and a C2-14 aryloxy group)),
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, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonyloxy group, (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkoxy group, the C1-10 alkoxycarbonyl group, the C1-10 alkylcarbonyloxy group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of: a carboxyl group, a nitro group, a cyano group, a halogen atom, a C1-10 alkoxy group, a C1-10 alkylcarbonyl group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonylamino group, an amino group, a mono- or di-C1-10 alkylamino group, a hydroxyl group, a protected hydroxyl group, a C2-14 aryl group and 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 group 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: a C1-10 alkyl group (the C1-10 alkyl group may be substituted with one or more halogen atoms), a C2-6 alkenyl group, a C2-6 alkynyl group, a carboxyl group, a nitro group, a cyano group, a halogen atom, a C1-10 alkoxy group, a C1-10 alkylcarbonyl group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonylamino group, an amino group, a mono- or di-C1-10 alkylamino group, a hydroxyl group, a protected hydroxyl group, a C2-14 aryl group and a C2-14 aryloxy group)
L2 is a bond, CR34R35 (wherein each of R34 and R35 is independently a hydrogen atom or a C1-6 alkyl group (the C1-6alkyl 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: a carboxyl group, a nitro group, a cyano group, a halogen atom, a C1-10 alkoxy group, a C1-10 alkylcarbonyl group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonylamino group, an amino group, a mono- or di-C1-10 alkylamino group, a hydroxyl group, a protected hydroxyl group, a C2-14 aryl group and 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 group 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: a C1-10 alkyl group (the C1-10 alkyl group may be substituted with one or more halogen atoms), a C2-6 alkenyl group, a C2-6 alkynyl group, a carboxyl group, a nitro group, a cyano group, a halogen atom, a C1-10 alkoxy group, a C1-10 alkylcarbonyl group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonylamino group, an amino group, a mono- or di-C1-10 alkylamino group, a hydroxyl group, a protected hydroxyl group, a C2-14 aryl group and a C2-14 aryloxy group))
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: a carboxyl group, a nitro group, a cyano group, a halogen atom, a C1-10 alkoxy group, a C1-10 alkylcarbonyl group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonylamino group, an amino group, a mono- or di-C1-10 alkylamino group, a hydroxyl group, a protected hydroxyl group, a C2-14 aryl group and 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 group 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: a C1-10 alkyl group (the C1-10 alkyl group may be substituted with one or more halogen atoms), a C2-6 alkenyl group, a C2-6 alkynyl group, a carboxyl group, a nitro group, a cyano group, a halogen atom, a C1-10 alkoxy group, a C1-10 alkylcarbonyl group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonylamino group, an amino group, a mono- or di-C1-10 alkylamino group, a hydroxyl group, a protected hydroxyl group, a C2-14 aryl group and a C2-14 aryloxy group)), 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 C1-10alkylcarbonyl 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: a carboxyl group, a nitro group, a cyano group, a halogen atom, a C1-10 alkoxy group, a C1-10 alkylcarbonyl group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonylamino group, an amino group, a mono- or di-C1-10 alkylamino group, a hydroxyl group, a protected hydroxyl group, a C2-14 aryl group and 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 group 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: a C1-10 alkyl group (the C1-10 alkyl group may be substituted with one or more halogen atoms), a C2-6 alkenyl group, a C2-6 alkynyl group, a carboxyl group, a nitro group, a cyano group, a halogen atom, a C1-10 alkoxy group, a C1-10 alkylcarbonyl group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonylamino group, an amino group, a mono- or di-C1-10 alkylamino group, a hydroxyl group, a protected hydroxyl group, a C2-14 aryl group and a C2-14 aryloxy group))
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: a carboxyl group, a nitro group, a cyano group, a halogen atom, a C1-10 alkoxy group, a C1-10 alkylcarbonyl group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonylamino group, an amino group, a mono- or di-C1-10alkylamino group, a hydroxyl group, a protected hydroxyl group, a C2-14 aryl group and 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 group 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: a C1-10 alkyl group (the C1-10 alkyl group may be substituted with one or more halogen atoms), a C2-6 alkenyl group, a C2-6 alkynyl group, a carboxyl group, a nitro group, a cyano group, a halogen atom, a C1-10 alkoxy group, a C1-10 alkylcarbonyl group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonylamino group, an amino group, a mono- or di-C1-10 alkylamino group, a hydroxyl group, a protected hydroxyl group, a C2-14 aryl group and a C2-14 aryloxy group)), an oxygen atom, a sulfur atom or 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: a carboxyl group, a nitro group, a cyano group, a halogen atom, a C1-10 alkoxy group, a C1-10 alkylcarbonyl group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonylamino group, an amino group, a mono- or di-C1-10 alkylamino group, a hydroxyl group, a protected hydroxyl group, a C2-14 aryl group and 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 group 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: a C1-10 alkyl group (the C1-10 alkyl group may be substituted with one or more halogen atoms), a C2-6 alkenyl group, a C2-6 alkynyl group, a carboxyl group, a nitro group, a cyano group, a halogen atom, a C1-10 alkoxy group, a C1-10 alkylcarbonyl group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonylamino group, an amino group, a mono- or di-C1-10 alkylamino group, a hydroxyl group, a protected hydroxyl group, a C2-14 aryl group and a C2-14 aryloxy group)),
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: a carboxyl group, a nitro group, a cyano group, a halogen atom, a C1-10 alkoxy group, a C1-10 alkylcarbonyl group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonylamino group, an amino group, a mono- or di-C1-10 alkylamino group, a hydroxyl group, a protected hydroxyl group, a C2-14 aryl group and 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 group 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: a C1-10 alkyl group (the C1-10 alkyl group may be substituted with one or more halogen atoms), a C2-6 alkenyl group, a C2-6 alkynyl group, a carboxyl group, a nitro group, a cyano group, a halogen atom, a C1-10 alkoxy group, a C1-10 alkylcarbonyl group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonylamino group, an amino group, a mono- or di-C1-10alkylamino group, a hydroxyl group, a protected hydroxyl group, a C2-14 aryl group and a C2-14 aryloxy group)), and
R3 is a C2-14 aryl group (the C2-14 aryl group may be 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), 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 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 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 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: a carboxyl group, a nitro group, a cyano group, a halogen atom, a C1-10 alkoxy group, a C1-10 alkylcarbonyl group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonylamino group, a amino group, a mono- or di-C1-10 alkylamino group, a hydroxyl group, a protected hydroxyl group, a C2-14 aryl group and 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 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: a C1-10 alkyl group (the C1-10 alkyl group may be substituted with one or more halogen atoms), a C2-6 alkenyl group, a C2-6 alkynyl group, a carboxyl group, a nitro group, a cyano group, a halogen atom, a C1-10 alkoxy group, a C1-10 alkylcarbonyl group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonylamino group, an amino group, a mono- or di-C1-10 alkylamino group, a hydroxyl group, a protected hydroxyl group, a thiol group, a phosphonic acid group, a sulfonic acid group, a tetrazole group, a C2-14 aryl group and a C2-14 aryloxy group), SO2R28, SOR28, COR28 (wherein R28 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: a carboxyl group, a nitro group, a cyano group, a halogen atom, a C1-10 alkoxy group, a C1-10 alkylcarbonyl group, C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, C1-10 alkylcarbonylamino group, an amino group, a mono- or di-C1-10 alkylamino group, a hydroxyl group, a protected hydroxyl group, a C2-14 aryl group and 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 group 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: a C1-10 alkyl group (the C1-10 alkyl group may be substituted with one or more halogen atoms), a C2-6 alkenyl group, a C2-6 alkynyl group, a carboxyl group, a nitro group, a cyano group, a halogen atom, a C1-10 alkoxy group, a C1-10 alkylcarbonyl group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonylamino group, an amino group, a mono- or di-C1-10 alkylamino group, a hydroxyl group, a protected hydroxyl group, a C2-14 aryl group and a C2-14 aryloxy group) or NR29R30 (wherein each of R29 and R30 is independently a hydrogen atom, a hydroxyl group, a formyl 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 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: a carboxyl group, a nitro group, a cyano group, a halogen atom, a C1-10 alkoxy group, a C1-10 alkylcarbonyl group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonylamino group, an amino group, a mono- or di-C1-10 alkylamino group, a hydroxyl group, a protected hydroxyl group, a C2-14 aryl group and 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 group 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: a C1-10 alkyl group (the C1-10 alkyl group may be substituted with one or more halogen atoms), a C2-6 alkenyl group, a C2-6 alkynyl group, a carboxyl group, a nitro group, a cyano group, a halogen atom, a C1-10 alkoxy group, a C1-10 alkylcarbonyl group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonylamino group, an amino group, a mono- or di-C1-10 alkylamino group, a hydroxyl group, a protected hydroxyl group, a C2-14 aryl group and a C2-14 aryloxy group), or R29 and R30, together with each other means —(CH2)m3-G-(CH2)m4— (wherein G is an oxygen atom, a sulfur atom, a CR31R32 (where in 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 C1-0 alkylcarbonyl group (the C1-10 alkyl group, the C2-6 alkenyl group, the C2-6 alkynyl group, the C1-10 alkoxy group, the C1-0 alkylcarbonyloxy group, the C1-10alkoxycarbonyl group and the C1-10 alkylcarbonyl group may be optionally substituted with one or more substituents selected from the group consisting of: a carboxyl group, a nitro group, a cyano group, a halogen atom, a C1-10 alkoxy group, a C1-10 alkylcarbonyl group, a C1-10 alkylcarbonyloxy group, C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonylamino group, an amino group, a mono- or di-C1-10 alkylamino group, a hydroxyl group, a protected hydroxyl group, a C2-14 aryl group and 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 group 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: a C1-10 alkyl group (the C1-10 alkyl group may be substituted with one or more halogen atoms), a C2-6 alkenyl group, a C2-6 alkynyl group, a carboxyl group, a nitro group, a cyano group, a halogen atom, a C1-10 alkoxy group, a C1-10 alkylcarbonyl group, a C1-10 alkylcarbonyloxy group, a C1-10 alkoxycarbonyl group, a C1-10 alkylcarbonylamino group, an amino group, a mono- or di-C1-10 alkylamino group, a hydroxyl group, a protected hydroxyl group, a C2-14 aryl group and a C2-14 aryloxy group)), 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)), a tautomer, prodrug or pharmaceutically acceptable salt of the compound or a solvate thereof.