	US 7,576,115 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 Aug. 13, 2007, as Appl. No. 11/837,659.
Application 11/837659 is a division of application No. 11/294609, filed on Dec. 06, 2005, granted, now 7,351,841.
Application 11/294609 is a continuation in part of application No. PCT/JP2004/008165, 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 2008/0027068 A1, Jan. 31, 2008
Int. Cl. A61K 31/415 (2006.01); C07D 231/10 (2006.01)

U.S. Cl. 514—406 [548/373.1; 548/375.1; 548/376.1]

112 Claims

1. A compound represented by the formula (1)

wherein

A is a nitrogen atom, and

B is NR⁹, wherein R⁹is a hydroxyl group, a formyl group, a C_1-10alkyl group, a C_2-6alkenyl group, a C_2-6alkynyl group, a C_1-10alkoxy group, a C_1-10alkylcarbonyloxy group, a C_1-10alkoxycarbonyl group, a C_1-10alkylcarbonyl group, the C_1-10alkyl group, the C_2-6alkenyl group, the C_2-6alkynyl group, the C_1-10alkoxy group, the C_2-6alkylcarbonyloxy group, the C_1-10alkoxycarbonyl group and the C_1-10alkylcarbonyl 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 C_1-10alkoxy group, a C_1-10alkylcarbonyl group, a C_1-10alkylcarbonyloxy group, a C_1-10alkoxycarbonyl group, a C_1-10alkylcarbonylamino group, an amino group, a mono- or di-C_1-10alkylamino group, a hydroxyl group, a protected hydroxyl group, a C_2-14aryl group and a C_2-14aryloxy group, the C_2-14aryl group and the C_2-14aryloxy group may be substituted with one or more C_1-6alkyl groups, the C_1-6alkyl group may be substituted with one or more halogen atoms, or one or more halogen atoms, a C_2-14aryl group, the C_2-14aryl group may be optionally substituted with one or more substituents selected from the group consisting of: a C_1-10alkyl group, the C_1-10alkyl group may be substituted with one or more halogen atoms, a C_2-6alkenyl group, a C_2-6alkynyl group, a carboxyl group, a nitro group, a cyano group, a halogen atom, a C_1-10alkoxy group, a C_1-10alkylcarbonyl group, a C_1-10alkylcarbonyloxy group, a C_1-10alkoxycarbonyl group, a C_1-10alkylcarbonylamino group, an amino group, a mono- or di-C_1-10alkylamino group, a hydroxyl group, a protected hydroxyl group, a C_2-14aryl group and a C_2-14aryloxy group, or a C_2-14aryloxy group, the C_2-14aryloxy group may be optionally substituted with one or more substituents selected from the group consisting of: a C_1-10alkyl group, the C_1-10alkyl group may be substituted with one or more halogen atoms, a C_2-6alkenyl group, a C_2-6alkynyl group, a carboxyl group, a nitro group, a cyano group, a halogen atom, a C_1-10alkoxy group, a C_1-10alkylcarbonyl group, a C_1-10alkylcarbonyloxy group, a C_1-10alkoxycarbonyl group, a C_1-10alkylcarbonylamino group, an amino group, a mono- or di-C_1-10alkylamino group, a hydroxyl group, a protected hydroxyl group, a C_2-14aryl group and a C_2-14aryloxy group,

R¹is a C_2-14aryl group, the C_2-14aryl 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 C_1-10alkyl group, a C_2-6alkenyl group, a C_2-6alkynyl group, a C_1-10alkoxy group, a C_1-10alkylcarbonyl group, a C_1-10alkylcarbonyloxy group, a C_1-10alkoxycarbonyl group, the C_1-10alkyl group, the C_2-6alkenyl group, the C_2-6alkynyl group, the C_1-10alkoxy group, the C_1-10alkylcarbonyl group, the C_1-10alkylcarbonyloxy group and the C_1-10alkoxycarbonyl 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 C_1-10alkoxy group, a C_1-10alkylcarbonyl group, a C_1-10alkylcarbonyloxy group, a C_1-10alkoxycarbonyl group, a C_1-10alkylcarbonylamino group, an amino group, a mono- or di-C_1-10alkylamino group, a hydroxyl group, a protected hydroxyl group, a C_2-14aryl group and a C_2-14aryloxy group, the C_2-14aryl group and the C_2-14aryloxy group may be substituted with one or more C_1-6alkyl groups, the C_1-6alkyl group may be substituted with one or more halogen atoms, or one or more halogen atoms, a C_2-14aryl group, the C_2-14aryl group may be optionally substituted with one or more substituents selected from the group consisting of: a C_1-10alkyl group, the C_1-10alkyl group may be substituted with one or more halogen atoms, a C_2-6alkenyl group, a C_2-6alkynyl group, a carboxyl group, a nitro group, a cyano group, a halogen atom, a C_1-10alkoxy group, a C_1-10alkylcarbonyl group, a C_1-10alkylcarbonyloxy group, a C_1-10alkoxycarbonyl group, a C_1-10alkylcarbonylamino group, an amino group, a mono- or di-C_1-10alkylamino group, a hydroxyl group, a protected hydroxyl group, a C_2-14aryl group and a C_2-14aryloxy 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 C_1-10alkyl group, a C_2-6alkenyl group, a C_2-6alkynyl group and a C_1-10alkylcarbonyl group, the C_1-10alkyl group, the C_1-6alkenyl group, the C_1-6alkynyl group and the C_1-10alkylcarbonyl 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 C_1-10alkoxy group, a C_1-10alkylcarbonyl group, a C_1-10alkylcarbonyloxy group, a C_1-10alkoxycarbonyl group, a C_1-10alkylcarbonylamino group, an amino group, a mono- or di-C_1-10alkylamino group, a hydroxyl group, a protected hydroxyl group, a C_2-14aryl group and a C_2-14aryloxy group, the C_2-14aryl group and the C_2-14aryloxy group may be substituted with one or more C_1-6alkyl groups, the C_1-6alkyl group may be substituted with one or more halogen atoms, or one or more halogen atoms,

L¹is a bond, CR¹⁰R¹¹, wherein each of R¹⁰and R¹¹is independently a hydrogen atom or a C_1-6alkyl group, the C_1-6alkyl group may be substituted with one or more halogen atoms)), an oxygen atom, a sulfur atom or NR¹², wherein R¹²is a hydrogen atom, a hydroxyl group, a formyl group, a C_1-10alkyl group, a C_2-6alkenyl group, a C_2-6alkynyl group, a C_1-10alkoxy group, a C_1-10alkylcarbonyloxy group, a C_1-10alkoxycarbonyl group, a C_1-10alkylcarbonyl group, the C_1-10alkyl group, the C_2-6alkenyl group, the C_2-6alkynyl group, the C_1-10alkoxy group, the C_1-10alkylcarbonyloxy group, the C_1-10alkoxycarbonyl group and the C_1-10alkylcarbonyl 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 C_1-10alkoxy group, a C_1-10alkylcarbonyl group, a C_1-10alkylcarbonyloxy group, a C_1-10alkoxycarbonyl group, a C_1-10alkylcarbonylamino group, an amino group, a mono- or di-C_1-10alkylamino group, a hydroxyl group, a protected hydroxyl group, a C_2-14aryl group and a C_2-14aryloxy group, the C_2-14aryl group and the C_2-14aryloxy group may be substituted with one or more C_1-6alkyl groups, the C_1-6alkyl group may be substituted with one or more halogen atoms, or one or more halogen atoms, or a C_2-14aryl group, the C_2-14aryl group may be optionally substituted with one or more substituents selected from the group consisting of: a C_1-10alkyl group, the C_1-10alkyl group may be substituted with one or more halogen atoms, a C_2-6alkenyl group, a C_2-6alkynyl group, a carboxyl group, a nitro group, a cyano group, a halogen atom, a C_1-10alkoxy group, a C_1-10alkylcarbonyl group, a C_1-10alkylcarbonyloxy group, a C_1-10alkoxycarbonyl group, a C_1-10alkylcarbonylamino group, an amino group, a mono- or di-C_1-10alkylamino group, a hydroxyl group, a protected hydroxyl group, a C_2-14aryl group and a C_2-14aryloxy group,

X is OR¹³, SR¹³or NR¹⁴R¹⁵, wherein R¹³is a hydrogen atom, a C_1-10alkyl group, a C_2-6alkenyl group, a C_2-6alkynyl group or a C_1-10alkylcarbonyl group, the C_1-10alkyl group, the C_2-6alkenyl group, the C_2-6alkynyl group and the C_1-10alkylcarbonyl 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 C_1-10alkoxy group, a C_1-10alkylcarbonyl group, a C_1-10alkylcarbonyloxy group, a C_1-10alkoxycarbonyl group, a C_1-10alkylcarbonylamino group, an amino group, a mono- or di-C_1-10alkylamino group, a hydroxyl group, a protected hydroxyl group, a C_2-14aryl group and a C_2-14aryloxy group, the C_2-14aryl group and the C_2-14aryloxy group may be substituted with one or more C_1-6alkyl groups, the C_1-6alkyl group may be substituted with one or more halogen atoms, or one or more halogen atoms, and each of R¹⁴and R¹⁵is independently a hydrogen atom, a formyl group, a C_1-10alkyl group, a C_2-6alkenyl group, a C_2-6alkynyl group, a C_1-10alkoxy group, a C_1-10alkylcarbonyl group, the C_1-10alkyl group, the C_2-6alkenyl group, the C_2-6alkynyl group, the C_1-10alkoxy group and the C_1-10alkylcarbonyl 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 C_1-10alkoxy group, a C_1-10alkylcarbonyl group, a C_1-10alkylcarbonyloxy group, a C_1-10alkoxycarbonyl group, a C_1-10alkylcarbonylamino group, an amino group, a mono- or di-C_1-10alkylamino group, a hydroxyl group, a protected hydroxyl group, a C_2-14aryl group and a C_2-14aryloxy group, the C_2-14aryl group and the C_2-14aryloxy group may be substituted with one or more C_1-6alkyl groups, the C_1-6alkyl group may be substituted with one or more halogen atoms, or one or more halogen atoms, or a C_2-14aryl group, the C_2-14aryl group may be optionally substituted with one or more substituents selected from the group consisting of: a C_1-10alkyl group, the C_1-10alkyl group may be substituted with one or more halogen atoms, a C_2-6alkenyl group, a C_1-6alkynyl group, a carboxyl group, a nitro group, a cyano group, a halogen atom, a C_1-10alkoxy group, a C_1-10alkylcarbonyl group, a C_1-10alkylcarbonyloxy group, a C_1-10alkoxycarbonyl group, a C_1-10alkylcarbonylamino group, an amino group, a mono- or di-C_1-10alkylamino group, a hydroxyl group, a protected hydroxyl group, a C_2-14aryl group and a C_2-14aryloxy group,

R²is a hydrogen atom, a formyl group, a C_1-10alkyl group, a C_1-6alkenyl group, a C_1-6alkynyl group, a C_1-10alkoxy group, a C_1-10alkylcarbonyl group, a C_1-10alkoxycarbonyl group, a C_1-10alkylcarbonyloxy group, the C_1-10alkyl group, the C_2-6alkenyl group, the C_1-6alkynyl group, the C_1-10alkoxy group, the C_1-10alkoxycarbonyl group, the C_1-10alkylcarbonyloxy group and the C_1-10alkylcarbonyl 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 C_1-10alkoxy group, a C_1-10alkylcarbonyl group, a C_1-10alkylcarbonyloxy group, a C_1-10alkoxycarbonyl group, a C_1-10alkylcarbonylamino group, an amino group, a mono- or di-C_1-10alkylamino group, a hydroxyl group, a protected hydroxyl group, a C_2-14aryl group and a C_2-14aryloxy group, the C_2-14aryl group and the C_2-14aryloxy group may be substituted with one or more C_1-6alkyl groups, the C_1-6alkyl group may be substituted with one or more halogen atoms, or one or more halogen atoms or a C_2-14aryl group, the C_2-14aryl group may be optionally substituted with one or more substituents selected from the group consisting of: a C_1-10alkyl group, the C_1-10alkyl group may be substituted with one or more halogen atoms, a C_2-6alkenyl group, a C_2-6alkynyl group, a carboxyl group, a nitro group, a cyano group, a halogen atom, a C_1-10alkoxy group, a C_1-10alkylcarbonyl group, a C_1-10alkylcarbonyloxy group, a C_1-10alkoxycarbonyl group, a C_1-10alkylcarbonylamino group, an amino group, a mono- or di-C_1-10alkylamino group, a hydroxyl group, a protected hydroxyl group, a C_2-14aryl group and a C_2-14aryloxy group,

L²is a bond, CR³⁴R³⁵, wherein each of R³⁴and R³⁵is independently a hydrogen atom or a C_1-6alkyl group, the C_1-6alkyl group may be substituted with one or more halogen atoms, an oxygen atom, a sulfur atom or NR¹⁶, wherein R¹⁶is a hydrogen atom, a hydroxyl group, a formyl group, a C_1-10alkyl group, a C_2-6alkenyl group, a C_2-6alkynyl group, a C_1-10alkoxy group, a C_1-10alkylcarbonyloxy group, a C_1-10alkoxycarbonyl group, a C_1-10alkylcarbonyl group, the C_1-10alkyl group, the C_2-6alkenyl group, the C_2-6alkynyl group, the C_1-10alkoxy group, the C_1-10alkylcarbonyloxy group, the C_1-10alkoxycarbonyl group and the C_1-10alkylcarbonyl 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 C_1-10alkoxy group, a C_1-10alkylcarbonyl group, a C_1-10alkylcarbonyloxy group, a C_1-10alkoxycarbonyl group, a C_1-10alkylcarbonylamino group, an amino group, a mono- or di-C_1-10alkylamino group, a hydroxyl group, a protected hydroxyl group, a C_2-14aryl group and a C_2-14aryloxy group, the C_2-14aryl group and the C_2-14aryloxy group may be substituted with one or more C_1-6alkyl groups, the C_1-6alkyl group may be substituted with one or more halogen atoms) or one or more halogen atoms, or a C_2-14aryl group, the C_2-14aryl group may be optionally substituted with one or more substituents selected from the group consisting of: a C_1-10alkyl group, the C_1-10alkyl group may be substituted with one or more halogen atoms, a C_2-6alkenyl group, a C_2-6alkynyl group, a carboxyl group, a nitro group, a cyano group, a halogen atom, a C_1-10alkoxy group, a C_1-10alkylcarbonyl group, a C_1-10alkylcarbonyloxy group, a C_1-10alkoxycarbonyl group, a C_1-10alkylcarbonylamino group, an amino group, a mono- or di-C_1-10alkylamino group, a hydroxyl group, a protected hydroxyl group, a C_2-14aryl group and a C_2-14aryloxy group,

L³is a bond, CR¹⁷R¹⁸, wherein each of R¹⁷and R¹⁸is independently a hydrogen atom, a C_1-10alkyl group, a C_1-6alkenyl group, a C_1-6alkynyl group, a C_1-10alkoxy group, a C_1-10alkylcarbonyl group, the C_1-10alkyl group, the C_1-6alkenyl group, the C_1-6alkynyl group, the C_1-10alkoxy group and the C_1-10alkylcarbonyl 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 C_1-10alkoxy group, a C_1-10alkylcarbonyl group, a C_2-6alkylcarbonyloxy group, a C_1-10alkoxycarbonyl group, a C_1-10alkylcarbonylamino group, an amino group, a mono- or di-C_1-10alkylamino group, a hydroxyl group, a protected hydroxyl group, a C_2-14aryl group and a C_2-14aryloxy group, the C_2-14aryl group and the C_2-14aryloxy group may be substituted with one or more C_1-6alkyl groups, the C_1-6alkyl group may be substituted with one or more halogen atoms, or one or more halogen atoms, or a C_2-14aryl group, the C_2-14aryl group may be optionally substituted with one or more substituents selected from the group consisting of: a C_1-10alkyl group, the C_1-10alkyl group may be substituted with one or more halogen atoms, a C_1-6alkenyl group, a C_1-6alkynyl group, a carboxyl group, a nitro group, a cyano group, a halogen atom, a C_1-10alkoxy group, a C_1-10alkylcarbonyl group, a C_1-10alkylcarbonyloxy group, a C_1-10alkoxycarbonyl group, a C_1-10alkylcarbonylamino group, an amino group, a mono- or di-C_1-10alkylamino group, a hydroxyl group, a protected hydroxyl group, a C_2-14aryl group and a C_2-14aryloxy group, an oxygen atom, a sulfur atom or NR¹⁹, wherein R¹⁹is a hydrogen atom, a hydroxyl group, a formyl group, a C_1-10alkyl group, a C_2-6alkenyl group, a C_2-6alkynyl group, a C_1-10alkoxy group, a C_1-10alkylcarbonyloxy group, a C_1-10alkoxycarbonyl group, a C_1-10alkylcarbonyl group, the C_1-10alkyl group, the C_2-6alkenyl group, the C_2-6alkynyl group, the C_1-10alkylcarbonyloxy group, the C_1-10alkoxycarbonyl group, the C_1-10alkoxy group and the C_1-10alkylcarbonyl 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 C_1-10alkoxy group, a C_1-10alkylcarbonyl group, a C_1-10alkylcarbonyloxy group, a C_1-10alkoxycarbonyl group, a C_1-10alkylcarbonylamino group, an amino group, a mono- or di-C_1-10alkylamino group, a hydroxyl group, a protected hydroxyl group, a C_2-14aryl group and a C_2-14aryloxy group, the C_2-14aryl group and the C_2-14aryloxy group may be substituted with one or more C_1-6alkyl groups, the C_1-6alkyl group may be substituted with one or more halogen atoms) or one or more halogen atoms, or a C_2-14aryl group, the C_2-14aryl group may be optionally substituted with one or more substituents selected from the group consisting of: a C_1-10alkyl group, the C_1-10alkyl group may be substituted with one or more halogen atoms, a C_2-6alkenyl group, a C_2-6alkynyl group, a carboxyl group, a nitro group, a cyano group, a halogen atom, a C_1-10alkoxy group, a C_1-10alkylcarbonyl group, a C_1-10alkylcarbonyloxy group, a C_1-10alkoxycarbonyl group, a C_1-10alkylcarbonylamino group, an amino group, a mono- or di-C_1-10alkylamino group, a hydroxyl group, a protected hydroxyl group, a C_2-14aryl group and a C_2-14aryloxy group,

L⁴is a bond CR²⁰R²¹, wherein each of R²⁰and R²¹is independently a hydrogen atom, a C_1-10alkyl group, a C_2-6alkenyl group, a C_2-6alkynyl group, a C_1-10alkoxy group, a C_1-10alkylcarbonyl group, the C_1-10alkyl group, the C_2-6alkenyl group, the C_2-6alkynyl group, the C_1-10alkoxy group and the C_1-10alkylcarbonyl 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 C_1-10alkoxy group, a C_1-10alkylcarbonyl group, a C_1-10alkylcarbonyloxy group, a C_1-10alkoxycarbonyl group, a C_1-10alkylcarbonylamino group, an amino group, a mono- or di-C_1-10alkylamino group, a hydroxyl group, a protected hydroxyl group, a C_2-14aryl group and a C_2-14aryloxy group, the C_2-14aryl group and the C_2-14aryloxy group may be substituted with one or more C_1-6alkyl groups, the C_1-6alkyl group may be substituted with one or more halogen atoms, or one or more halogen atoms, or a C_2-14aryl group, the C_2-14aryl group may be optionally substituted with one or more substituents selected from the group consisting of: a C_1-10alkyl group, the C_1-10alkyl group may be substituted with one or more halogen atoms, a C_2-6alkenyl group, a C_2-6alkynyl group, a carboxyl group, a nitro group, a cyano group, a halogen atom, a C_2-6alkoxy group, a C_1-10alkylcarbonyl group, a C_1-10alkylcarbonyloxy group, a C_1-10alkoxycarbonyl group, a C_1-10alkylcarbonylamino group, an amino group, a mono- or di-C_1-10alkylamino group, a hydroxyl group, a protected hydroxyl group, a C_2-14aryl group and a C_2-14aryloxy group, an oxygen atom, a sulfur atom or NR²²wherein R²²is a hydrogen atom, a hydroxyl group, a formyl group, a C_1-10alkyl group, a C_2-6alkenyl group, a C_2-6alkynyl group, a C_1-10alkoxy group, a C_1-10alkylcarbonyloxy group, a C_1-10alkoxycarbonyl group, a C_1-10alkylcarbonyl group, the C_1-10alkyl group, the C_2-6alkenyl group, the C_2-6alkynyl group, the C_1-10alkoxy group, the C_1-10alkylcarbonyloxy group, the C_1-10alkoxycarbonyl group and the C_1-10alkylcarbonyl 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 C_1-10alkoxy group, a C_1-10alkylcarbonyl group, a C_1-10alkylcarbonyloxy group, a C_1-10alkoxycarbonyl group, a C_1-10alkylcarbonylamino group, an amino group, a mono- or di-C_1-10alkylamino group, a hydroxyl group, a protected hydroxyl group, a C_2-14aryl group and a C_2-14aryloxy group, the C_2-14aryl group and the C_2-14aryloxy group may be substituted with one or more C_1-6alkyl groups, the C_1-6alkyl group may be substituted with one or more halogen atoms) or one or more halogen atoms, or a C_2-14aryl group, the C_2-14aryl group may be optionally substituted with one or more substituents selected from the group consisting of: a C_1-10alkyl group (the C_1-10alkyl group may be substituted with one or more halogen atoms, a C_2-6alkenyl group, a C_2-6alkynyl group, a carboxyl group, a nitro group, a cyano group, a halogen atom, a C_1-10alkoxy group, a C_1-10alkylcarbonyl group, a C_1-10alkylcarbonyloxy group, a C_1-10alkoxycarbonyl group, a C_1-10alkylcarbonylamino group, an amino group, a mono- or di-C_1-10alkylamino group, a hydroxyl group, a protected hydroxyl group, a C_2-14aryl group and a C_2-14aryloxy group,

Y is an oxygen atom, a sulfur atom or NR²³, wherein R²³is a hydrogen atom, a hydroxyl group, a formyl group, a C_1-10alkyl group, a C_2-6alkenyl group, a C_2-6alkynyl group, a C_1-10alkoxy group, a C_1-10alkylcarbonyloxy group, a C_1-10alkoxycarbonyl group, a C_1-10alkylcarbonyl group, the C_1-10alkyl group, the C_2-6alkenyl group, the C_2-6alkynyl group, the C_1-10alkoxy group, the C_1-10alkylcarbonyloxy group, the C_1-10alkoxycarbonyl group and the C_1-10alkylcarbonyl 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 C_1-10alkoxy group, a C_1-10alkylcarbonyl group, a C_1-10alkylcarbonyloxy group, a C_1-10alkoxycarbonyl group, a C_1-10alkylcarbonylamino group, an amino group, a mono- or di-C_1-10alkylamino group, a hydroxyl group, a protected hydroxyl group, a C_2-14aryl group and a C_2-14aryloxy group (the C_2-14aryl group and the C_2-14aryloxy group may be substituted with one or more C_1-6alkyl groups the C_1-6alkyl group may be substituted with one or more halogen atoms, or one or more halogen atoms, or a C_2-14aryl group, the C_2-14aryl group may be substituted with one or more substituents selected from the group consisting of: a C_1-10alkyl group, the C_1-10alkyl group may be substituted with one or more halogen atoms, a C_2-6alkenyl group, a C_2-6alkynyl group, a carboxyl group, a nitro group, a cyano group, a halogen atom, a C_1-10alkoxy group, a C_1-10alkylcarbonyl group, a C_1-10alkylcarbonyloxy group, a C_1-10alkoxycarbonyl group, a C_1-10alkylcarbonylamino group, an amino group, a mono- or di-C_1-10alkylamino group, a hydroxyl group, a protected hydroxyl group, a C_2-14aryl group and a C_2-14aryloxy group)), and

R³is a C_2-14aryl group, the C_2-14aryl group may be substituted with one or more substituents independently represented by —W¹(CW²W³)_mW⁴, wherein W¹is (CR²⁴R²⁵)_n, wherein each of R²⁴and R²⁵is independently a hydrogen atom or a C_1-6alkyl group, the C_1-6alkyl 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 R³⁶is a hydrogen atom, a C_1-6alkyl group, a formyl group or a C_1-6alkylcarbonyl group, each of W²and W³is independently a hydrogen atom or a C_1-3alkyl group, the C_1-3alkyl group may be substituted with one or more halogen atoms, m is 0, 1, 2 or 3, and W⁴is a hydroxyl group, a thiol group, an amino group, a formyl group, a halogen atom, a nitro group, a cyano group, a C_1-10alkyl group, a C_1-6alkenyl group, a C_2-6alkynyl group, a C_1-10alkoxy group, a C_1-10alkylcarbonyloxy group, a C_1-10alkylcarbonylamino group, a mono- or di-C_1-10alkylamino group (the C_1-10alkyl group, the C_2-6alkenyl group, the C_2-6alkynyl group, the C_1-10alkoxy group, the C_1-10alkylcarbonyloxy group, the C_1-10alkylcarbonylamino group and the mono- or di-C_1-10alkylamino 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 C_1-10alkoxy group, a C_1-10alkylcarbonyl group, a C_1-10alkylcarbonyloxy group, a C_1-10alkoxycarbonyl group, a C_1-10alkylcarbonylamino group, a amino group, a mono- or di-C_1-10alkylamino group, a hydroxyl group, a protected hydroxyl group, a C_2-14aryl group and a C_2-14aryloxy group (the C_2-14aryl group and the C_2-14aryloxy group may be substituted with one or more C_1-6alkyl groups (the C_1-6alkyl group may be substituted with one or more halogen atoms) or one or more halogen atoms)), a C_2-14aryl group (the C_2-14aryl group may be optionally substituted with one or more substituents selected from the group consisting of: a C_1-10alkyl group (the C_1-10alkyl group may be substituted with one or more halogen atoms), a C_2-6alkenyl group, a C_2-6alkynyl group, a carboxyl group, a nitro group, a cyano group, a halogen atom, a C_1-10alkoxy group, a C_1-10alkylcarbonyl group, a C_1-10alkylcarbonyloxy group, a C_1-10alkoxycarbonyl group, a C_1-10alkylcarbonylamino group, an amino group, a mono- or di-C_1-10alkylamino group, a hydroxyl group, a protected hydroxyl group, a thiol group, a phosphonic acid group, a sulfonic acid group, a tetrazole group, a C_2-14aryl group and a C_2-14aryloxy group), SO₂R²⁸, SOR²⁸, COR₂₈, wherein R²⁸is a hydroxyl group, a C_1-10alkyl group, a C_2-6alkenyl group, a C_2-6alkynyl group, a C_1-10alkoxy group, the C_1-10alkyl group, the C_2-6alkenyl group, the C_2-6alkynyl group and the C_1-10alkoxy 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 C_1-10alkoxy group, a C_1-10alkylcarbonyl group, C_1-10alkylcarbonyloxy group, a C_1-10alkoxycarbonyl group, C_1-10alkylcarbonylamino group, an amino group, a mono- or di-C_1-10alkylamino group, a hydroxyl group, a protected hydroxyl group, a C_2-14aryl group and a C_2-14aryloxy group, the C_2-14aryl group and the C_2-14aryloxy group may be substituted with one or more C_1-6alkyl groups, the C_1-6alkyl group may be substituted with one or more halogen atoms, or one or more halogen atoms, a C_2-14aryl group, a C_2-14aryloxy group the C_2-14aryl group and the C_2-14aryloxy group may be optionally substituted with one or more substituents selected from the group consisting of: a C_1-10alkyl group, the C_1-10alkyl group may be substituted with one or more halogen atoms, a C_2-6alkenyl group, a C_2-6alkynyl group, a carboxyl group, a nitro group, a cyano group, a halogen atom, a C_1-10alkoxy group, a C_1-10alkylcarbonyl group, a C_1-10alkylcarbonyloxy group, a C_1-10alkoxycarbonyl group, a C_1-10alkylcarbonylamino group, an amino group, a mono- or di-C_1-10alkylamino group, a hydroxyl group, a protected hydroxyl group, a C_2-14aryl group and a C_2-14aryloxy group, or NR²⁹R³⁰, wherein each of R²⁹and R³⁰is independently a hydrogen atom, a hydroxyl group, a formyl group, a cyano group, a C_1-10alkyl group, a C_2-6alkenyl group, a C_2-6alkynyl group, a C_1-10alkoxy group, a C_1-10alkylcarbonyloxy group, a C_1-10alkoxycarbonyl group, a C_1-20alkylcarbonyl group the C_1-10alkyl group, the C_2-6alkenyl group, the C_2-6alkynyl group, the C_1-10alkoxy group, the C_1-10alkylcarbonyloxy group, the C_1-10alkoxycarbonyl group and the C_1-10alkylcarbonyl 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 C_1-10alkoxy group, a C_1-10alkylcarbonyl group, a C_1-10alkylcarbonyloxy group, a C_1-10alkoxycarbonyl group, a C_1-10alkylcarbonylamino group, an amino group, a mono- or di-C_1-10alkylamino group, a hydroxyl group, a protected hydroxyl group, a C_2-14aryl group and a C_2-14aryloxy group, the C_2-14aryl group and the C_2-14aryloxy group may be substituted with one or more C_1-6alkyl groups, the C_1-6alkyl group may be substituted with one or more halogen atoms, or one or more halogen atoms or a C_2-14aryl group, the C_2-14aryl group may be optionally substituted with one or more substituents selected from the group consisting of: a C_1-10alkyl group, the C_1-10alkyl group may be substituted with one or more halogen atoms, a C_2-6alkenyl group, a C_2-6alkynyl group, a carboxyl group, a nitro group, a cyano group, a halogen atom, a C_1-10alkoxy group, a C_1-10alkylcarbonyl group, a C_1-10alkylcarbonyloxy group, a C_1-10alkoxycarbonyl group, a C_1-10alkylcarbonylamino group, an amino group, a mono- or di-C_1-10alkylamino group, a hydroxyl group, a protected hydroxyl group, a C_2-14aryl group and a C_2-14aryloxy group, or R²⁹and R³⁰, together with each other means —(CH₂)_m3—G—(CH₂)_m4—, wherein G is an oxygen atom, a sulfur atom, a CR³¹R³², wherein each of R³¹and R³²is independently a hydrogen atom, a C_1-10alkyl group, a C_2-14aryl group, a C_1-10alkoxy group, a C_2-14aryloxy group, a hydroxyl group or a protected hydroxyl group, or NR³³, wherein R³³is a hydrogen atom, a hydroxyl group, a formyl group, a C_1-10alkyl group, a C_2-6alkenyl group, C_2-6alkynyl group, a C_1-10alkoxy group, a C_1-10alkylcarbonyloxy group, a C_1-10alkoxycarbonyl group, a C_1-10alkylcarbonyl group, the C_1-10alkyl group, the C_2-6alkenyl group, the C_2-6alkynyl group, the C_1-10alkoxy group, the C_1-10alkylcarbonyloxy group, the C_1-10alkoxycarbonyl group and the C_1-10alkylcarbonyl 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 C_1-10alkoxy group, a C_1-10alkylcarbonyl group, a C_1-10alkylcarbonyloxy group, C_1-10alkoxycarbonyl group, a C_1-10alkylcarbonylamino group, an amino group, a mono- or di-C_1-10alkylamino group, a hydroxyl group, a protected hydroxyl group, a C_2-14aryl group and a C_2-14aryloxy group, the C_2-14aryl group and the C_2-14aryloxy group may be substituted with one or more C_1-6alkyl groups, the C_1-6alkyl group may be substituted with one or more halogen atoms, or one or more halogen atoms or a C_2-14aryl group, the C_2-14aryl group may be optionally substituted with one or more substituents selected from the group consisting of: a C_1-10alkyl group, the C_1-10alkyl group may be substituted with one or more halogen atoms, a C_2-6alkenyl group, a C_2-6alkynyl group, a carboxyl group, a nitro group, a cyano group, a halogen atom, a C_1-10alkoxy group, a C_1-10alkylcarbonyl group, a C_1-10alkylcarbonyloxy group, a C_1-10alkoxycarbonyl group, a C_1-10alkylcarbonylamino group, an amino group, a mono- or di-C_1-10alkylamino group, a hydroxyl group, a protected hydroxyl group, a C_2-14aryl group and a C_2-14aryloxy 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.