TECHNICAL FIELD

The present invention relates bicyclic heterocyclyl compounds, and an inhibitor of semaphorin, a promotor of center/peripheral nerve regeneration, a medicament for preventing/treating nerve injury disease, a medicament for preventing/treating neurological disease associated with neurodegeneration or ischemic deficit, or a medicament for preventing/treating corneal disease, which comprises the bicyclic heterocyclyl compound as an active ingredient.

BACKGROUND ART

Semaphorins are endogenous proteins which are identified as a factor that can retract the nerve growth cone and suppress the axonal growth. Until now, about 20 kinds of molecular species thereof have been known. Amongst them, class type 3 subfamily gene cluster has been studied the most. The proteins that these genes encode are known to have in vitro potent activities for inhibiting neurite outgrowth and retracting growth cone. Amongst them, semaphorin 3A (Sema3A) (Non-Patent Literatures 1 and 2) has been studied the most, which can induce the growth cone retraction in cultural neuron, in a low concentration of 10 pM and in a short time.

Some substances inhibiting the Sema3A function have been already known, such as a certain group of xanthone compounds which are obtained from the culture ofPenicilliumsp. SPF-3059 strain (International Patent Organism Depositary, National Institute of Advanced Industrial Science and Technology, Accession number: FERM BP-7663) (Patent Literatures 1 and 2), and xanthone derivatives which are obtained by chemically-modifying the above xanthane compounds (Patent Literature 3).

And, it has been reported that the compounds can promote re-elongating the nerve fiber in spinal cord of a rat spinal cord injury model (Patent Literature 4 and Non-Patent Literature 3) and can promote regenerating the corneal sensory neuron of a mouse corneal graft model (Patent Literature 5 and Non-Patent Literature 4).

PRIOR ART

Patent Reference

[Patent Literature 1] WO 2002/09756[Patent Literature 2] WO 2003/062243[Patent Literature 3] WO 2003/062440[Patent Literature 4] WO 2012/018069[Patent Literature 5] WO 2012/115182

Non-Patent Reference

[Non-Patent Literature 1] Cell, 75, p 217 (1993)[Non-Patent Literature 2] Cell, 75, p 1389 (1993)[Non-Patent Literature 3] Nature Medicine, volume 3, Number 12, p 1398 (2006)[Non-Patent Literature 4] PLOS ONE, volume 7, Issue 11, e47716 (2012)

SUMMARY OF INVENTION

Technical Problem

The purpose of the present invention may be to provide an inhibitor of semaphorin having a novel chemical structure, and a promotor of center/peripheral nerve regeneration, a medicament for preventing/treating nerve injury disease, a medicament for preventing/treating neurological disease associated with neurodegeneration or ischemic deficit, a medicament for preventing/treating corneal disease such as dry eye, or the like, which comprises the new inhibitor of semaphorin as an active ingredient.

Solution to Problem

The present inventors have extensively studied to reach the above object, and then have found that a compound of formula (1) or a pharmaceutically acceptable salt thereof (hereinafter, it may be referred to as “the present compound”) has a semaphorin inhibitory activity, and thereby the present compound may be a useful medicament for treating or preventing neuropathic disease, neurodegenerative disease, neurological disease associated with ischemic deficit, and corneal disease. Based upon the new findings, the present invention has been completed.

The present invention can show as follows.

Term 1

A compound of formula (1):


or a pharmaceutically acceptable salt thereof
wherein

R1-L- is R1—OC(O)— or R1—NHC(O)—;

R1is

(i) hydrogen atom,

(ii) optionally-substituted C1-6alkyl group,

(iii) optionally-substituted C2-6alkenyl group,

(iv) optionally-substituted C2-6alkynyl group,

(v) optionally-substituted 3- to 8-membered cycloalkyl group,

(vi) optionally-substituted 4- to 8-membered cycloalkenyl group,

(vii) optionally-substituted 4- to 8-membered saturated aliphatic heterocyclyl group,

(viii) optionally-substituted 5- to 10-membered unsaturated aliphatic heterocyclyl group,

(ix) optionally-substituted 6- to 10-membered aryl group, or

(x) optionally-substituted 5- to 10-membered heteroaryl group;

R2is hydrogen atom, hydroxy group, or carboxyl group; and

Ring A is a group of formula (2) or (3):


wherein R3is

(i) hydrogen atom,

(ii) optionally-substituted C1-6alkyl group,

(iii) optionally-substituted C2-6alkenyl group,

(iv) optionally-substituted C2-6alkynyl group,

(v) optionally-substituted 3- to 8-membered cycloalkyl group,

(vi) optionally-substituted 4- to 8-membered cycloalkenyl group,

(vii) optionally-substituted 4- to 8-membered saturated aliphatic heterocyclyl group,

(viii) optionally-substituted 5- to 10-membered unsaturated aliphatic heterocyclyl group,

(ix) optionally-substituted 6- to 10-membered aryl group, or

(x) optionally-substituted 5- to 10-membered heteroaryl group,

the part of XYZ is X═Y—Z, X—Y═Z, or X—Y—Z,

X is nitrogen atom, NR4, or oxygen atom, provided that X is not oxygen atom in the case of formula (2),

R4is

(i) hydrogen atom,

(ii) optionally-substituted C1-6alkyl group,

(iii) optionally-substituted C2-6alkenyl group,

(iv) optionally-substituted C2-6alkynyl group,

(v) optionally-substituted 3- to 8-membered cycloalkyl group,

(vi) optionally-substituted 4- to 8-membered cycloalkenyl group,

(vii) optionally-substituted 4- to 8-membered saturated aliphatic heterocyclyl group,

(viii) optionally-substituted 5- to 10-membered unsaturated aliphatic heterocyclyl group,

(ix) optionally-substituted 6- to 10-membered aryl group, or

(x) optionally-substituted 5- to 10-membered heteroaryl group,

Y is carbon atom or CH, and

Z is carbon atom, CH, or nitrogen atom, provided that the combination of X, Y, and Z should be any one of chemically-possible selections.

Term 2

The compound of Term 1 or a pharmaceutically acceptable salt thereof, which is represented by formula (1′):


wherein

R1-L- is R1—OC(O)— or R1—NHC(O)—;

R1is

(i) hydrogen atom,

(ii) optionally-substituted C1-6alkyl group,

(iii) optionally-substituted C2-6alkenyl group,

(iv) optionally-substituted C2-6alkynyl group,

(v) optionally-substituted 3- to 8-membered cycloalkyl group,

(vi) optionally-substituted 4- to 8-membered cycloalkenyl group,

(vii) optionally-substituted 4- to 8-membered saturated aliphatic heterocyclyl group,

(viii) optionally-substituted 5- to 10-membered unsaturated aliphatic heterocyclyl group,

(ix) optionally-substituted 6- to 10-membered aryl group, or

(x) optionally-substituted 5- to 10-membered heteroaryl group,

wherein the substituent(s) of the (ii) optionally-substituted C1-6alkyl group is one or more substituents selected independently from the group consisting of hydroxy group, methoxy group, ethoxy group, carboxyl group, carbamoyl group (which may be substituted with one or two the same or different C1-3alkyl), NR5R6(wherein R5and R6are independently hydrogen atom, C1-3alkyl group, carboxylmethyl group, 2-hydroxyethyl group, or 2-aminoethyl group), optionally-substituted 3- to 6-membered cycloalkyl group (wherein the substituent(s) of said optionally-substituted 3- to 6-membered cycloalkyl group is one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, C1-3alkyl group, hydroxy group, and carboxyl group), optionally-substituted 4- to 6-membered saturated aliphatic heterocyclyl group (wherein the substituent(s) of said optionally-substituted 4- to 6-membered saturated aliphatic heterocyclyl group is one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, C1-3alkyl group, hydroxy group, and carboxyl group), and optionally-substituted 5- to 10-membered heteroaryl group (wherein the substituent (s) of said optionally-substituted 5- to 10-membered heteroaryl group is one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, C1-3alkyl group, hydroxy group, and carboxyl group), or

the (ii) optionally-substituted C1-6alkyl group may be any one of the following groups of formulae (4)-(6):

formula (4):



wherein m is 1, 2, 3, 4, or 5, R7is C1-3alkoxy group, amino acid group (which binds to C(O) at its N terminus), and peptide consisting of 2-3 amino acid residues (which binds to C(O) at its N terminus),
formula (5):
R8-L2-(CH2CH2O)qCH2CH2(5)

wherein q is 1, 2, 3, 4, or 5, L2is single bond or C(O), R8is hydroxy group, C1-3alkoxy group, amino group which may be substituted with one or two the same or different C1-3alkyl, amino acid group (which binds to L2at its N terminus), or peptide consisting of 2-3 amino acid residues (which binds to L2at its N terminus),

formula (6):



wherein L3is CH2or C(O), and R9is hydroxy group, C1-3alkoxy group, amino group which may be substituted with one or two the same or different C1-3alkyl, amino acid group (which binds to L3at its N terminus), or peptide consisting of 2-3 amino acid residues (which binds to L3at its N terminus),

the substituent(s) of the (iii) optionally-substituted C2-6alkenyl group, and the (iv) optionally-substituted C2-6alkynyl group are independently one or more substituents selected independently from the group consisting of hydroxy group, methoxy group, ethoxy group, carboxyl group, carbamoyl group (which may be substituted with one or two the same or different C1-3alkyl), NR5R6(wherein R5and R6are independently hydrogen atom, C1-3alkyl group, carboxylmethyl group, 2-hydroxyethyl group, or 2-aminoethyl group), optionally-substituted 3- to 6-membered cycloalkyl group (wherein the substituent (s) of said optionally-substituted 3- to 6-membered cycloalkyl group is one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, hydroxy group, and carboxyl group), optionally-substituted 4- to 6-membered saturated aliphatic heterocyclyl group (wherein the substituent(s) of said optionally-substituted 4- to 6-membered saturated aliphatic heterocyclyl group is one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, C1-3alkyl group, hydroxy group, and carboxyl group), and 5- to 10-membered heteroaryl group,

the substituent(s) of the (v) optionally-substituted 3- to 8-membered cycloalkyl group, the (vi) optionally-substituted 4- to 8-membered cycloalkenyl group, the (vii) optionally-substituted 4- to 8-membered saturated aliphatic heterocyclyl group, the (viii) optionally-substituted 5- to 10-membered unsaturated aliphatic heterocyclyl group, the (ix) optionally-substituted 6- to 10-membered aryl group, and the (x) optionally-substituted 5- to 10-membered heteroaryl group are independently one or more substituents selected independently from the group consisting of hydroxy group, methoxy group, ethoxy group, amino group which may be substituted with one or two the same or different C1-3alkyl, and carboxyl group;

R2is hydrogen atom, hydroxy group, or carboxyl group; and

Ring A is a group of formula (2′) or (3′):


wherein R3is

(i) hydrogen atom,

(ii) optionally-substituted C1-6alkyl group,

(iii) optionally-substituted C2-6alkenyl group,

(iv) optionally-substituted C2-6alkynyl group,

(v) optionally-substituted 3- to 8-membered cycloalkyl group,

(vi) optionally-substituted 4- to 8-membered cycloalkenyl group,

(vii) optionally-substituted 4- to 8-membered saturated aliphatic heterocyclyl group,

(viii) optionally-substituted 5- to 10-membered unsaturated aliphatic heterocyclyl group,

(ix) optionally-substituted 6- to 10-membered aryl group, or

(x) optionally-substituted 5- to 10-membered heteroaryl group,

wherein the substituent(s) of the (ii) optionally-substituted C1-6alkyl group, the (iii) optionally-substituted C2-6alkenyl group, the (iv) optionally-substituted C2-6alkynyl group, the (v) optionally-substituted 3- to 8-membered cycloalkyl group, the (vi) optionally-substituted 4- to 8-membered cycloalkenyl group, the (vii) optionally-substituted 4- to 8-membered saturated aliphatic heterocyclyl group, the (viii) optionally-substituted 5- to 10-membered unsaturated aliphatic heterocyclyl group, the (ix) optionally-substituted 6- to 10-membered aryl group, and the (x) optionally-substituted 5- to 10-membered heteroaryl group are independently one or more substituents selected independently from the group consisting of hydroxy group, methoxy group, ethoxy group, carboxyl group, carbamoyl group which may be substituted with one or two the same or different C1-3alkyl, and amino group which may be substituted with one or two the same or different C1-3alkyl,

the part of XYZ is X═Y—Z, X—Y═Z, or X—Y—Z,

X is nitrogen atom, NR4, or oxygen atom, provided that X is not oxygen atom in the case of formula (2′),

R4is

(i) hydrogen atom,

(ii) optionally-substituted C1-6alkyl group,

(iii) optionally-substituted C2-6alkenyl group,

(iv) optionally-substituted C2-6alkynyl group,

(v) optionally-substituted 3- to 8-membered cycloalkyl group,

(vi) optionally-substituted 4- to 8-membered cycloalkenyl group,

(vii) optionally-substituted 4- to 8-membered saturated aliphatic heterocyclyl group,

(viii) optionally-substituted 5- to 10-membered unsaturated aliphatic heterocyclyl group,

(ix) optionally-substituted 6- to 10-membered aryl group, or

(x) optionally-substituted 5- to 10-membered heteroaryl group,

wherein the substituent (s) of the (ii) optionally-substituted C1-6alkyl group, the (iii) optionally-substituted C2-6alkenyl group, the (iv) optionally-substituted C2-6alkynyl group, the (v) optionally-substituted 3- to 8-membered cycloalkyl group, the (vi) optionally-substituted 4- to 8-membered cycloalkenyl group, the (vii) optionally-substituted 4- to 8-membered saturated aliphatic heterocyclyl group, the (viii) optionally-substituted 5- to 10-membered unsaturated aliphatic heterocyclyl group, the (ix) optionally-substituted 6- to 10-membered aryl group, and the (x) optionally-substituted 5- to 10-membered heteroaryl group are independently one or more substituents selected independently from the group consisting of hydroxy group, methoxy group, ethoxy group, carboxyl group, carbamoyl group which may be substituted with one or two the same or different C1-3alkyl, and amino group which may be substituted with one or two the same or different C1-3alkyl,

Y is carbon atom or CH, and

Z is carbon atom, CH, or nitrogen atom, provided that the combination of X, Y, and Z should be any one of chemically-possible selections.

The compounds of formula (1) in Term 1 include those of formula (1′). The groups of formulae (2) and (3) in Term 1 include those of formulae (2′) and (3′).

Term 3

The compound of Term 2 or a pharmaceutically acceptable salt thereof, wherein R2is hydrogen atom.

Term 4

The compound of Term 2 or 3 or a pharmaceutically acceptable salt thereof, wherein R3is (i) hydrogen atom, (ii) C1-3alkyl group, or (v) 3- to 6-membered cycloalkyl group.

Term 5

The compound of any one of Terms 2-4 or a pharmaceutically acceptable salt thereof, wherein R3is hydrogen atom or methyl group.

Term 6

The compound of any one of Terms 2-5 or a pharmaceutically acceptable salt thereof, wherein R4is (i) hydrogen atom, (ii) C1-3alkyl group, or (v) 3- to 6-membered cycloalkyl group.

Term 7

The compound of any one of Terms 2-6 or a pharmaceutically acceptable salt thereof, wherein R4is methyl group.

Term 8

The compound of any one of Terms 2-7 or a pharmaceutically acceptable salt thereof, wherein

R1is (i) hydrogen atom, or (ii) optionally-substituted C1-6alkyl group,

wherein the substituent(s) of the (ii) optionally-substituted C1-6alkyl group is one or more substituents selected independently from the group consisting of hydroxy group, methoxy group, ethoxy group, carboxyl group, carbamoyl group (which may be substituted with one or two the same or different C1-3alkyl), NR5R6(wherein R5and R6are independently hydrogen atom, C1-3alkyl group, carboxylmethyl group, 2-hydroxyethyl group, or 2-aminoethyl group), optionally-substituted 3- to 6-membered cycloalkyl group (wherein the substituent(s) of said optionally-substituted 3- to 6-membered cycloalkyl group is one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, C1-3alkyl group, hydroxy group, and carboxyl group), optionally-substituted 4- to 6-membered saturated aliphatic heterocyclyl group (wherein the substituent(s) of said optionally-substituted 4- to 6-membered saturated aliphatic heterocyclyl group is one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, C1-3alkyl group, hydroxy group, and carboxyl group), and optionally-substituted 5- to 10-membered heteroaryl group (wherein the substituent (s) of said optionally-substituted 5- to 10-membered heteroaryl group is one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, C1-3alkyl group, hydroxy group, and carboxyl group), or

the (ii) optionally-substituted C1-6alkyl group may be any one of the groups of formulae (4)-(6).

Term 9

The compound of any one of Terms 2-7 or a pharmaceutically acceptable salt thereof, wherein

R1is

(i) hydrogen atom,

(ii) optionally-substituted C1-3alkyl group,

(iii) optionally-substituted C2-4alkenyl group,

(iv) optionally-substituted C2-4alkynyl group,

(v) optionally-substituted 3- to 6-membered cycloalkyl group,

(vi) optionally-substituted 4- to 6-membered cycloalkenyl group,

(vii) optionally-substituted 4- to 6-membered saturated aliphatic heterocyclyl group,

(viii) optionally-substituted 5- to 6-membered unsaturated aliphatic heterocyclyl group,

(ix) optionally-substituted 6- to 10-membered aryl group, or

(x) optionally-substituted 5- to 10-membered heteroaryl group,

wherein the substituent(s) of the (ii) optionally-substituted C1-3alkyl group is one or more substituents selected independently from the group consisting of hydroxy group, methoxy group, ethoxy group, carboxyl group, carbamoyl group (which may be substituted with one or two the same or different C1-3alkyl), NR5R6(wherein R5and R6are independently hydrogen atom, C1-3alkyl group, carboxylmethyl group, 2-hydroxyethyl group, or 2-aminoethyl group), optionally-substituted 3- to 6-membered cycloalkyl group (wherein the substituent(s) of said optionally-substituted 3- to 6-membered cycloalkyl group is one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, C1-3alkyl group, hydroxy group, and carboxyl group), optionally-substituted 4- to 6-membered saturated aliphatic heterocyclyl group (wherein the substituent(s) of said optionally-substituted 4- to 6-membered saturated aliphatic heterocyclyl group is one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, C1-3alkyl group, hydroxy group, and carboxyl group), and optionally-substituted 5- to 10-membered heteroaryl group (wherein the substituent (s) of said optionally-substituted 5- to 10-membered heteroaryl group is one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, C1-3alkyl group, hydroxy group, and carboxyl group), or

the (ii) optionally-substituted C1-3alkyl group may be any one of the groups of formulae (4)-(6),

in formula (4), m is 1, R7is amino acid group (which binds to C(O) at its N terminus),

in formula (5), q is 1, 2, 3, 4, or 5, L2is single bond or C(O), R8is hydroxy group or amino acid group (which binds to L2at its N terminus),

in formula (6), L3is C(O), R9is hydroxy group or amino acid group (which binds to L3at its N terminus),

the substituent (s) of the (iii) optionally-substituted C2-4alkenyl group, and the (iv) optionally-substituted C2-4alkynyl group are independently one or more substituents selected independently from the group consisting of hydroxy group, methoxy group, ethoxy group, carboxyl group, carbamoyl group (which may be substituted with one or two the same or different C1-3alkyl), NR5R6(wherein R5and R6are independently hydrogen atom, C1-3alkyl group, carboxylmethyl group, 2-hydroxyethyl group, or 2-aminoethyl group), optionally-substituted 3- to 6-membered cycloalkyl group (wherein the substituent(s) of said optionally-substituted 3- to 6-membered cycloalkyl group is one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, hydroxy group, and carboxyl group), optionally-substituted 4- to 6-membered saturated aliphatic heterocyclyl group (wherein the substituent(s) of said optionally-substituted 4- to 6-membered saturated aliphatic heterocyclyl group is one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, C1-3alkyl group, hydroxy group, and carboxyl group), and 5- to 10-membered heteroaryl group,

the substituent(s) of the (v) optionally-substituted 3- to 6-membered cycloalkyl group, the (vi) optionally-substituted 4- to 6-membered cycloalkenyl group, the (vii) optionally-substituted 4- to 6-membered saturated aliphatic heterocyclyl group, the (viii) optionally-substituted 5- to 6-membered unsaturated aliphatic heterocyclyl group, the (ix) optionally-substituted 6- to 10-membered aryl group, and the (x) optionally-substituted 5- to 10-membered heteroaryl group are independently one or more substituents selected independently from the group consisting of hydroxy group, methoxy group, ethoxy group, amino group which may be substituted with one or two the same or different C1-3alkyl, and carboxyl group.

Term 10

The compound of any one of Terms 2-9 or a pharmaceutically acceptable salt thereof, wherein

R1is (i) hydrogen atom, or (ii) optionally-substituted C1-3alkyl group,

wherein the substituent(s) of the (ii) optionally-substituted C1-3alkyl group is one or more substituents selected independently from the group consisting of hydroxy group, methoxy group, ethoxy group, carboxyl group, carbamoyl group (which may be substituted with one or two the same or different C1-3alkyl), NR5R6(wherein R5and R6are independently hydrogen atom, C1-3alkyl group, carboxylmethyl group, 2-hydroxyethyl group, or 2-aminoethyl group), optionally-substituted 3- to 6-membered cycloalkyl group (wherein the substituent (s) of said optionally-substituted 3- to 6-membered cycloalkyl group is one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, C1-3alkyl group, hydroxy group, and carboxyl group), optionally-substituted 4- to 6-membered saturated aliphatic heterocyclyl group (wherein the substituent(s) of said optionally-substituted 4- to 6-membered saturated aliphatic heterocyclyl group is one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, C1-3alkyl group, hydroxy group, and carboxyl group), and optionally-substituted 5- to 10-membered heteroaryl group (wherein the substituent (s) of said optionally-substituted 5- to 10-membered heteroaryl group is one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, C1-3alkyl group, hydroxy group, and carboxyl group), or

the (ii) optionally-substituted C1-3alkyl group may be any one of the groups of formulae (4)-(6),

in formula (4), m is 1, R7is amino acid group (which binds to C(O) at its N terminus),

in formula (5), q is 1, 2, 3, 4, or 5, L2is single bond or C(O), R8is hydroxy group or amino acid group (which binds to L2at its N terminus),

in formula (6), L3is C(O), R9is hydroxy group or amino acid group (which binds to L3at its N terminus).

Term 11

The compound of any one of Terms 2-10 or a pharmaceutically acceptable salt thereof, wherein

R1is hydrogen atom, or the group of formula (6),

in formula (6), L3is C(O), R9is amino acid group (which binds to L3at its N terminus).

Term 12

The compound of any one of Terms 2-11 or a pharmaceutically acceptable salt thereof, wherein Ring A is the group of formula (2′).

Term 13

The compound of Term 12 or a pharmaceutically acceptable salt thereof, wherein the part of XYZ in formula (2′) is N═C—CH, N═C—N, NR4—C═C, NR4—CH—N, or NR4—CH—CH.

Term 14

The compound of Term 12 or 13 or a pharmaceutically acceptable salt thereof, wherein the part of XYZ in formula (2′) is N═C—N or NR4—C═C.

Term 15

The compound of any one of Terms 2-11 or a pharmaceutically acceptable salt thereof, wherein Ring A is the group of formula (3′).

Term 16

The compound of Term 15 or a pharmaceutically acceptable salt thereof, wherein the part of XYZ in formula (3′) is N═C—CH, N═C—N, NR4—C═C, NR4—CH—N, NR4—CH—CH, O—C═C, O—CH—N, or O—CH—CH.

Term 17

The compound of Term 15 or 16 or a pharmaceutically acceptable salt thereof, wherein the part of XYZ in formula (3′) is NR4—C═C or O—C═C.

Term 18

The compound of Term 2 or a pharmaceutically acceptable salt thereof, wherein

R1is

(ii) optionally-substituted C1-6alkyl group,

(iii) optionally-substituted C2-6alkenyl group,

(iv) optionally-substituted C2-6alkynyl group,

(v) optionally-substituted 3- to 8-membered cycloalkyl group,

(vi) optionally-substituted 4- to 8-membered cycloalkenyl group,

(vii) optionally-substituted 4- to 8-membered saturated aliphatic heterocyclyl group,

(viii) optionally-substituted 5- to 10-membered unsaturated aliphatic heterocyclyl group,

(ix) optionally-substituted 6- to 10-membered aryl group, or

(x) optionally-substituted 5- to 10-membered heteroaryl group,

wherein the substituent(s) of the (ii) optionally-substituted C1-6alkyl group is one or more substituents selected independently from the group consisting of hydroxy group, methoxy group, ethoxy group, carboxyl group, carbamoyl group (which may be substituted with one or two the same or different C1-3alkyl), NR5R6(wherein R5and R6are independently hydrogen atom, C1-3alkyl group, carboxylmethyl group, 2-hydroxyethyl group, or 2-aminoethyl group), optionally-substituted 3- to 6-membered cycloalkyl group (wherein the substituent(s) of said optionally-substituted 3- to 6-membered cycloalkyl group is one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, C1-3alkyl group, hydroxy group, and carboxyl group), optionally-substituted 4- to 6-membered saturated aliphatic heterocyclyl group (wherein the substituent(s) of said optionally-substituted 4- to 6-membered saturated aliphatic heterocyclyl group is one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, C1-3alkyl group, hydroxy group, and carboxyl group), and optionally-substituted 5- to 10-membered heteroaryl group (wherein the substituent (s) of said optionally-substituted 5- to 10-membered heteroaryl group is one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, C1-3alkyl group, hydroxy group, and carboxyl group), or

the (ii) optionally-substituted C1-6alkyl group may be any one of the groups of formulae (4)-(6),

in formula (4), m is 1, 2, 3, 4, or 5, R7is amino acid group (which binds to C(O) at its N terminus), or peptide consisting of 2-3 amino acid residues (which binds to C(O) at its N terminus),

in formula (5), q is 1, 2, 3, 4, or 5, L2is single bond or C(O), R8is hydroxy group, amino group which may be substituted with one or two the same or different C1-3alkyl, amino acid group (which binds to L2at its N terminus), or peptide consisting of 2-3 amino acid residues (which binds to L2at its N terminus),

in formula (6), L3is CH2or C(O), R9is hydroxy group, amino group which may be substituted with one or two the same or different C1-3alkyl, amino acid group (which binds to L3at its N terminus), or peptide consisting of 2-3 amino acid residues (which binds to L3at its N terminus),

the substituent (s) of the (iii) optionally-substituted C2-6alkenyl group, and the (iv) optionally-substituted C2-6alkynyl group are independently one or more substituents selected independently from the group consisting of hydroxy group, methoxy group, ethoxy group, carboxyl group, carbamoyl group (which may be substituted with one or two the same or different C1-3alkyl), NR5R6(wherein R5and R6are independently hydrogen atom, C1-3alkyl group, carboxylmethyl group, 2-hydroxyethyl group, or 2-aminoethyl group), optionally-substituted 3- to 6-membered cycloalkyl group (wherein the substituent(s) of said optionally-substituted 3- to 6-membered cycloalkyl group is one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, hydroxy group, and carboxyl group), optionally-substituted 4- to 6-membered saturated aliphatic heterocyclyl group (wherein the substituent(s) of said optionally-substituted 4- to 6-membered saturated aliphatic heterocyclyl group is one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, C1-3alkyl group, hydroxy group, and carboxyl group), and 5- to 10-membered heteroaryl group,

the substituent(s) of the (v) optionally-substituted 3- to 8-membered cycloalkyl group, the (vi) optionally-substituted 4- to 8-membered cycloalkenyl group, the (vii) optionally-substituted 4- to 8-membered saturated aliphatic heterocyclyl group, the (viii) optionally-substituted 5- to 10-membered unsaturated aliphatic heterocyclyl group, the (ix) optionally-substituted 6- to 10-membered aryl group, and the (x) optionally-substituted 5- to 10-membered heteroaryl group are independently one or more substituents selected independently from the group consisting of hydroxy group, methoxy group, ethoxy group, amino group which may be substituted with one or two the same or different C1-3alkyl, and carboxyl group;

R2is hydrogen atom; and

Ring A is a group of formula (2′) or (3′),

when Ring A is a group of formula (2′), R3is (i) hydrogen atom, (ii) C1-3alkyl group, or (v) 3- to 6-membered cycloalkyl group, the part of XYZ is N═C—N or NR4—C═C wherein R4is (i) hydrogen atom, (ii) C1-3alkyl group, or (v) 3- to 6-membered cycloalkyl group,

when Ring A is a group of formula (3′), R3is (i) hydrogen atom, (ii) C1-3alkyl group, or (v) 3- to 6-membered cycloalkyl group, the part of XYZ is NR4—C═C or O—C═C wherein R4is (i) hydrogen atom, (ii) C1-3alkyl group, or (v) 3- to 6-membered cycloalkyl group.

Term 19

The compound of Term 2 or 18 or a pharmaceutically acceptable salt thereof, wherein

R1is (i) hydrogen atom, or (ii) optionally-substituted C1-6alkyl group,

wherein the substituent(s) of the (ii) optionally-substituted C1-6alkyl group is one or more substituents selected independently from the group consisting of hydroxy group, methoxy group, ethoxy group, carboxyl group, carbamoyl group (which may be substituted with one or two the same or different C1-3alkyl), NR5R6(wherein R5and R6are independently hydrogen atom, C1-3alkyl group, carboxylmethyl group, 2-hydroxyethyl group, or 2-aminoethyl group), optionally-substituted 3- to 6-membered cycloalkyl group (wherein the substituent(s) of said optionally-substituted 3- to 6-membered cycloalkyl group is one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, C1-3alkyl group, hydroxy group, and carboxyl group), optionally-substituted 4- to 6-membered saturated aliphatic heterocyclyl group (wherein the substituent(s) of said optionally-substituted 4- to 6-membered saturated aliphatic heterocyclyl group is one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, C1-3alkyl group, hydroxy group, and carboxyl group), and optionally-substituted 5- to 10-membered heteroaryl group (wherein the substituent (s) of said optionally-substituted 5- to 10-membered heteroaryl group is one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, C1-3alkyl group, hydroxy group, and carboxyl group), or

the (ii) optionally-substituted C1-6alkyl group may be any one of the groups of formulae (4)-(6),

in formula (4), m is 1, 2, 3, 4, or 5, R7is amino acid group (which binds to C(O) at its N terminus), or peptide consisting of 2-3 amino acid residues (which binds to C(O) at its N terminus),

in formula (5), q is 1, 2, 3, 4, or 5, L2is single bond or C(O), R8is hydroxy group, amino group which may be substituted with one or two the same or different C1-3alkyl, amino acid group (which binds to L2at its N terminus), or peptide consisting of 2-3 amino acid residues (which binds to L2at its N terminus),

in formula (6), L3is CH2or C(O), R9is hydroxy group, amino group which may be substituted with one or two the same or different C1-3alkyl, amino acid group (which binds to L3at its N terminus), or peptide consisting of 2-3 amino acid residues (which binds to L3at its N terminus);

R2is hydrogen atom; and

Ring A is a group of formula (2′) or (3′),

when Ring A is a group of formula (2′), R3is (i) hydrogen atom, (ii) C1-3alkyl group, or (v) 3- to 6-membered cycloalkyl group, the part of XYZ is N═C—N or NR4—C═C wherein R4is (i) hydrogen atom, (ii) C1-3alkyl group, or (v) 3- to 6-membered cycloalkyl group,

when Ring A is a group of formula (3′), R3is (i) hydrogen atom, (ii) C1-3alkyl group, or (v) 3- to 6-membered cycloalkyl group, the part of XYZ is NR4—C═C or O—C═C wherein R4is (i) hydrogen atom, (ii) C1-3alkyl group, or (v) 3- to 6-membered cycloalkyl group.

Term 20

The compound of Term 2 or 18 or a pharmaceutically acceptable salt thereof, wherein

R1is

(i) hydrogen atom,

(ii) optionally-substituted C1-3alkyl group,

(iii) optionally-substituted C2-4alkenyl group,

(iv) optionally-substituted C2-4alkynyl group,

(v) optionally-substituted 3- to 6-membered cycloalkyl group,

(vi) optionally-substituted 4- to 6-membered cycloalkenyl group,

(vii) optionally-substituted 4- to 6-membered saturated aliphatic heterocyclyl group,

(viii) optionally-substituted 5- to 6-membered unsaturated aliphatic heterocyclyl group,

(ix) optionally-substituted 6- to 10-membered aryl group, or

(x) optionally-substituted 5- to 10-membered heteroaryl group,

wherein the substituent(s) of the (ii) optionally-substituted C1-3alkyl group is one or more substituents selected independently from the group consisting of hydroxy group, methoxy group, ethoxy group, carboxyl group, carbamoyl group (which may be substituted with one or two the same or different C1-3alkyl), NR5R6(wherein R5and R6are independently hydrogen atom, C1-3alkyl group, carboxylmethyl group, 2-hydroxyethyl group, or 2-aminoethyl group), optionally-substituted 3- to 6-membered cycloalkyl group (wherein the substituent(s) of said optionally-substituted 3- to 6-membered cycloalkyl group is one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, C1-3alkyl group, hydroxy group, and carboxyl group), optionally-substituted 4- to 6-membered saturated aliphatic heterocyclyl group (wherein the substituent(s) of said optionally-substituted 4- to 6-membered saturated aliphatic heterocyclyl group is one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, C1-3alkyl group, hydroxy group, and carboxyl group), and optionally-substituted 5- to 10-membered heteroaryl group (wherein the substituent (s) of said optionally-substituted 5- to 10-membered heteroaryl group is one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, C1-3alkyl group, hydroxy group, and carboxyl group), or

the (ii) optionally-substituted C1-3alkyl group may be any one of the groups of formulae (4)-(6),

in formula (4), m is 1, R7is amino acid group (which binds to C(O) at its N terminus),

in formula (5), q is 1, 2, 3, 4, or 5, L2is single bond or C(O), R8is hydroxy group or amino acid group (which binds to L2at its N terminus),

in formula (6), L3is C(O), R9is hydroxy group or amino acid group (which binds to L3at its N terminus),

the substituent (s) of the (iii) optionally-substituted C2-4alkenyl group, and the (iv) optionally-substituted C2-4alkynyl group are independently one or more substituents selected independently from the group consisting of hydroxy group, methoxy group, ethoxy group, carboxyl group, carbamoyl group (which may be substituted with one or two the same or different C1-3alkyl), NR5R6(wherein R5and R6are independently hydrogen atom, C1-3alkyl group, carboxylmethyl group, 2-hydroxyethyl group, or 2-aminoethyl group), optionally-substituted 3- to 6-membered cycloalkyl group (wherein the substituent(s) of said optionally-substituted 3- to 6-membered cycloalkyl group is one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, hydroxy group, and carboxyl group), optionally-substituted 4- to 6-membered saturated aliphatic heterocyclyl group (wherein the substituent(s) of said optionally-substituted 4- to 6-membered saturated aliphatic heterocyclyl group is one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, C1-3alkyl group, hydroxy group, and carboxyl group), and 5- to 10-membered heteroaryl group,

the substituent(s) of the (v) optionally-substituted 3- to 6-membered cycloalkyl group, the (vi) optionally-substituted 4- to 6-membered cycloalkenyl group, the (vii) optionally-substituted 4- to 6-membered saturated aliphatic heterocyclyl group, the (viii) optionally-substituted 5- to 6-membered unsaturated aliphatic heterocyclyl group, the (ix) optionally-substituted 6- to 10-membered aryl group, and the (x) optionally-substituted 5- to 10-membered heteroaryl group are independently one or more substituents selected independently from the group consisting of hydroxy group, methoxy group, ethoxy group, amino group which may be substituted with one or two the same or different C1-3alkyl, and carboxyl group;

R2is hydrogen atom; and

Ring A is a group of formula (2′) or (3′),

when Ring A is a group of formula (2′), R3is (i) hydrogen atom, (ii) C1-3alkyl group, or (v) 3- to 6-membered cycloalkyl group, the part of XYZ is N═C—N or NR4—C═C wherein R4is (i) hydrogen atom, (ii) C1-3alkyl group, or (v) 3- to 6-membered cycloalkyl group,

when Ring A is a group of formula (3′), R3is (i) hydrogen atom, (ii) C1-3alkyl group, or (v) 3- to 6-membered cycloalkyl group, the part of XYZ is NR4—C═C or O—C═C wherein R4is (i) hydrogen atom, (ii) C1-3alkyl group, or (v) 3- to 6-membered cycloalkyl group.

Term 21

The compound of any one of Terms 2 and 18-20 or a pharmaceutically acceptable salt thereof, wherein

R1is (i) hydrogen atom, or (ii) optionally-substituted C1-3alkyl group,

wherein the substituent(s) of the (ii) optionally-substituted C1-3alkyl group is one or more substituents selected independently from the group consisting of hydroxy group, methoxy group, ethoxy group, carboxyl group, carbamoyl group (which may be substituted with one or two the same or different C1-3alkyl), NR5R6(wherein R5and R6are independently hydrogen atom, C1-3alkyl group, carboxylmethyl group, 2-hydroxyethyl group, or 2-aminoethyl group), optionally-substituted 3- to 6-membered cycloalkyl group (wherein the substituent (s) of said optionally-substituted 3- to 6-membered cycloalkyl group is one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, C1-3alkyl group, hydroxy group, and carboxyl group), optionally-substituted 4- to 6-membered saturated aliphatic heterocyclyl group (wherein the substituent(s) of said optionally-substituted 4- to 6-membered saturated aliphatic heterocyclyl group is one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, C1-3alkyl group, hydroxy group, and carboxyl group), and optionally-substituted 5- to 10-membered heteroaryl group (wherein the substituent (s) of said optionally-substituted 5- to 10-membered heteroaryl group is one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, C1-3alkyl group, hydroxy group, and carboxyl group), or

the (ii) optionally-substituted C1-3alkyl group may be any one of the groups of formulae (4)-(6),

in formula (4), m is 1, R7is amino acid group (which binds to C(O) at its N terminus),

in formula (5), q is 1, 2, 3, 4, or 5, L2is single bond or C(O), R8is hydroxy group or amino acid group (which binds to L2at its N terminus),

in formula (6), L3is C(O), R9is hydroxy group or amino acid group (which binds to L3at its N terminus);

R2is hydrogen atom; and

Ring A is a group of formula (2′) or (3′),

when Ring A is a group of formula (2′), R3is (i) hydrogen atom, (ii) C1-3alkyl group, or (v) 3- to 6-membered cycloalkyl group, the part of XYZ is N═C—N or NR4—C═C wherein R4is (i) hydrogen atom, (ii) C1-3alkyl group, or (v) 3- to 6-membered cycloalkyl group,

when Ring A is a group of formula (3′), R3is (i) hydrogen atom, (ii) C1-3alkyl group, or (v) 3- to 6-membered cycloalkyl group, the part of XYZ is NR4—C═C or O—C═C wherein R4is (i) hydrogen atom, (ii) C1-3alkyl group, or (v) 3- to 6-membered cycloalkyl group.

Term 22

The compound of Term 2 or 18 or a pharmaceutically acceptable salt thereof, wherein

R1is

(ii) optionally-substituted C1-6alkyl group,

(iii) optionally-substituted C2-6alkenyl group,

(iv) optionally-substituted C2-6alkynyl group,

(v) optionally-substituted 3- to 8-membered cycloalkyl group,

(vi) optionally-substituted 4- to 8-membered cycloalkenyl group,

(vii) optionally-substituted 4- to 8-membered saturated aliphatic heterocyclyl group,

(viii) optionally-substituted 5- to 10-membered unsaturated aliphatic heterocyclyl group,

(ix) optionally-substituted 6- to 10-membered aryl group, or

(x) optionally-substituted 5- to 10-membered heteroaryl group,

wherein the substituent(s) of the (ii) optionally-substituted C1-6alkyl group is one or more substituents selected independently from the group consisting of hydroxy group, methoxy group, ethoxy group, carboxyl group, carbamoyl group (which may be substituted with one or two the same or different C1-3alkyl), NR5R6(wherein R5and R6are independently hydrogen atom, C1-3alkyl group, carboxylmethyl group, 2-hydroxyethyl group, or 2-aminoethyl group), optionally-substituted 3- to 6-membered cycloalkyl group (wherein the substituent (s) of said optionally-substituted 3- to 6-membered cycloalkyl group is one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, C1-3alkyl group, hydroxy group, and carboxyl group), optionally-substituted 4- to 6-membered saturated aliphatic heterocyclyl group (wherein the substituent(s) of said optionally-substituted 4- to 6-membered saturated aliphatic heterocyclyl group is one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, C1-3alkyl group, hydroxy group, and carboxyl group), and optionally-substituted 5- to 10-membered heteroaryl group (wherein the substituent (s) of said optionally-substituted 5- to 10-membered heteroaryl group is one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, C1-3alkyl group, hydroxy group, and carboxyl group), or

the (ii) optionally-substituted C1-6alkyl group may be any one of the groups of formulae (4)-(6),

in formula (4), m is 1, 2, 3, 4, or 5, R7is amino acid group (which binds to C(O) at its N terminus), or peptide consisting of 2-3 amino acid residues (which binds to C(O) at its N terminus),

in formula (5), q is 1, 2, 3, 4, or 5, L2is single bond or C(O), R8is hydroxy group, amino group which may be substituted with one or two the same or different C1-3alkyl, amino acid group (which binds to L2at its N terminus), or peptide consisting of 2-3 amino acid residues (which binds to L2at its N terminus),

in formula (6), L3is CH2or C(O), R9is hydroxy group, amino group which may be substituted with one or two the same or different C1-3alkyl, amino acid group (which binds to L3at its N terminus), or peptide consisting of 2-3 amino acid residues (which binds to L3at its N terminus),

the substituent (s) of the (iii) optionally-substituted C2-6alkenyl group, and the (iv) optionally-substituted C2-6alkynyl group are independently one or more substituents selected independently from the group consisting of hydroxy group, methoxy group, ethoxy group, carboxyl group, carbamoyl group (which may be substituted with one or two the same or different C1-3alkyl), NR5R6(wherein R5and R6are independently hydrogen atom, C1-3alkyl group, carboxylmethyl group, 2-hydroxyethyl group, or 2-aminoethyl group), optionally-substituted 3- to 6-membered cycloalkyl group (wherein the substituent (s) of said optionally-substituted 3- to 6-membered cycloalkyl group is one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, hydroxy group, and carboxyl group), optionally-substituted 4- to 6-membered saturated aliphatic heterocyclyl group (wherein the substituent(s) of said optionally-substituted 4- to 6-membered saturated aliphatic heterocyclyl group is one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, C1-3alkyl group, hydroxy group, and carboxyl group), and 5- to 10-membered heteroaryl group,

the substituent(s) of the (v) optionally-substituted 3- to 8-membered cycloalkyl group, the (vi) optionally-substituted 4- to 8-membered cycloalkenyl group, the (vii) optionally-substituted 4- to 8-membered saturated aliphatic heterocyclyl group, the (viii) optionally-substituted 5- to 10-membered unsaturated aliphatic heterocyclyl group, the (ix) optionally-substituted 6- to 10-membered aryl group, and the (x) optionally-substituted 5- to 10-membered heteroaryl group are independently one or more substituents selected independently from the group consisting of hydroxy group, methoxy group, ethoxy group, amino group which may be substituted with one or two the same or different C1-3alkyl, and carboxyl group;

R2is hydrogen atom; and

Ring A is a group of formula (2′) or (3′),

when Ring A is a group of formula (2′), R3is hydrogen atom or methyl group, the part of XYZ is N═C—N or NCH3—C═C,

when Ring A is a group of formula (3′), R3is hydrogen atom or methyl group, the part of XYZ is NCH3—C═C Or O—C═C.

Term 23

The compound of any one of Terms 2, 18, 19, and 22 or a pharmaceutically acceptable salt thereof, wherein

R1is (i) hydrogen atom, or (ii) optionally-substituted C1-6alkyl group,

wherein the substituent(s) of the (ii) optionally-substituted C1-6alkyl group is one or more substituents selected independently from the group consisting of hydroxy group, methoxy group, ethoxy group, carboxyl group, carbamoyl group (which may be substituted with one or two the same or different C1-3alkyl), NR5R6(wherein R5and R6are independently hydrogen atom, C1-3alkyl group, carboxylmethyl group, 2-hydroxyethyl group, or 2-aminoethyl group), optionally-substituted 3- to 6-membered cycloalkyl group (wherein the substituent (s) of said optionally-substituted 3- to 6-membered cycloalkyl group is one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, C1-3alkyl group, hydroxy group, and carboxyl group), optionally-substituted 4- to 6-membered saturated aliphatic heterocyclyl group (wherein the substituent(s) of said optionally-substituted 4- to 6-membered saturated aliphatic heterocyclyl group is one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, C1-3alkyl group, hydroxy group, and carboxyl group), and optionally-substituted 5- to 10-membered heteroaryl group (wherein the substituent (s) of said optionally-substituted 5- to 10-membered heteroaryl group is one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, C1-3alkyl group, hydroxy group, and carboxyl group), or

the (ii) optionally-substituted C1-6alkyl group may be any one of the groups of formulae (4)-(6),

in formula (4), m is 1, 2, 3, 4, or 5, R7is amino acid group (which binds to C(O) at its N terminus), or peptide consisting of 2-3 amino acid residues (which binds to C(O) at its N terminus),

in formula (5), q is 1, 2, 3, 4, or 5, L2is single bond or C(O), R8is hydroxy group, amino group which may be substituted with one or two the same or different C1-3alkyl, amino acid group (which binds to L2at its N terminus), or peptide consisting of 2-3 amino acid residues (which binds to L2at its N terminus),

in formula (6), L3is CH2or C(O), R9is hydroxy group, amino group which may be substituted with one or two the same or different C1-3alkyl, amino acid group (which binds to L3at its N terminus), or peptide consisting of 2-3 amino acid residues (which binds to L3at its N terminus);

R2is hydrogen atom; and

Ring A is a group of formula (2′) or (3′),

when Ring A is a group of formula (2′), R3is hydrogen atom or methyl group, the part of XYZ is N═C—N or NCH3—C═C,

when Ring A is a group of formula (3′), R3is hydrogen atom or methyl group, the part of XYZ is NCH3—C═C or O—C═C.

Term 24

The compound of any one of Terms 2, 18, 20, and 22 or a pharmaceutically acceptable salt thereof, wherein

R1is

(i) hydrogen atom,

(ii) optionally-substituted C1-3alkyl group,

(iii) optionally-substituted C2-4alkenyl group,

(iv) optionally-substituted C2-4alkynyl group,

(v) optionally-substituted 3- to 6-membered cycloalkyl group,

(vi) optionally-substituted 4- to 6-membered cycloalkenyl group,

(vii) optionally-substituted 4- to 6-membered saturated aliphatic heterocyclyl group,

(viii) optionally-substituted 5- to 6-membered unsaturated aliphatic heterocyclyl group,

(ix) optionally-substituted 6- to 10-membered aryl group, or

(x) optionally-substituted 5- to 10-membered heteroaryl group,

wherein the substituent (s) of the (ii) optionally-substituted C1-3alkyl group is one or more substituents selected independently from the group consisting of hydroxy group, methoxy group, ethoxy group, carboxyl group, carbamoyl group (which may be substituted with one or two the same or different C1-3alkyl), NR5R6(wherein R5and R6are independently hydrogen atom, C1-3alkyl group, carboxylmethyl group, 2-hydroxyethyl group, or 2-aminoethyl group), optionally-substituted 3- to 6-membered cycloalkyl group (wherein the substituent (s) of said optionally-substituted 3- to 6-membered cycloalkyl group is one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, C1-3alkyl group, hydroxy group, and carboxyl group), optionally-substituted 4- to 6-membered saturated aliphatic heterocyclyl group (wherein the substituent(s) of said optionally-substituted 4- to 6-membered saturated aliphatic heterocyclyl group is one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, C1-3alkyl group, hydroxy group, and carboxyl group), and optionally-substituted 5- to 10-membered heteroaryl group (wherein the substituent (s) of said optionally-substituted 5- to 10-membered heteroaryl group is one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, C1-3alkyl group, hydroxy group, and carboxyl group), or

the (ii) optionally-substituted C1-3alkyl group may be any one of the groups of formulae (4)-(6),

in formula (4), m is 1, R7is amino acid group (which binds to C(O) at its N terminus),

in formula (5), q is 1, 2, 3, 4, or 5, L2is single bond or C(O), R8is hydroxy group or amino acid group (which binds to L2at its N terminus),

in formula (6), L3is C(O), R9is hydroxy group or amino acid group (which binds to L3at its N terminus),

the substituent (s) of the (iii) optionally-substituted C2-4alkenyl group, and the (iv) optionally-substituted C2-4alkynyl group are independently one or more substituents selected independently from the group consisting of hydroxy group, methoxy group, ethoxy group, carboxyl group, carbamoyl group (which may be substituted with one or two the same or different C1-3alkyl), NR5R6(wherein R5and R6are independently hydrogen atom, C1-3alkyl group, carboxylmethyl group, 2-hydroxyethyl group, or 2-aminoethyl group), optionally-substituted 3- to 6-membered cycloalkyl group (wherein the substituent(s) of said optionally-substituted 3- to 6-membered cycloalkyl group is one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, hydroxy group, and carboxyl group), optionally-substituted 4- to 6-membered saturated aliphatic heterocyclyl group (wherein the substituent(s) of said optionally-substituted 4- to 6-membered saturated aliphatic heterocyclyl group is one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, C1-3alkyl group, hydroxy group, and carboxyl group), and 5- to 10-membered heteroaryl group,

the substituent(s) of the (v) optionally-substituted 3- to 6-membered cycloalkyl group, the (vi) optionally-substituted 4- to 6-membered cycloalkenyl group, the (vii) optionally-substituted 4- to 6-membered saturated aliphatic heterocyclyl group, the (viii) optionally-substituted 5- to 6-membered unsaturated aliphatic heterocyclyl group, the (ix) optionally-substituted 6- to 10-membered aryl group, and the (x) optionally-substituted 5- to 10-membered heteroaryl group are independently one or more substituents selected independently from the group consisting of hydroxy group, methoxy group, ethoxy group, amino group which may be substituted with one or two the same or different C1-3alkyl, and carboxyl group;

R2is hydrogen atom; and

Ring A is a group of formula (2′) or (3′),

when Ring A is a group of formula (2′), R3is hydrogen atom or methyl group, the part of XYZ is N═C—N or NCH3—C═C,

when Ring A is a group of formula (3′), R3is hydrogen atom or methyl group, the part of XYZ is NCH3—C═C or O—C═C.

Term 25

The compound of any one of Terms 2 and 18-24 or a pharmaceutically acceptable salt thereof, wherein

R1is (i) hydrogen atom, or (ii) optionally-substituted C1-3alkyl group,

wherein the substituent(s) of the (ii) optionally-substituted C1-3alkyl group is one or more substituents selected independently from the group consisting of hydroxy group, methoxy group, ethoxy group, carboxyl group, carbamoyl group (which may be substituted with one or two the same or different C1-3alkyl), NR5R6(wherein R5and R6are independently hydrogen atom, C1-3alkyl group, carboxylmethyl group, 2-hydroxyethyl group, or 2-aminoethyl group), optionally-substituted 3- to 6-membered cycloalkyl group (wherein the substituent(s) of said optionally-substituted 3- to 6-membered cycloalkyl group is one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, C1-3alkyl group, hydroxy group, and carboxyl group), optionally-substituted 4- to 6-membered saturated aliphatic heterocyclyl group (wherein the substituent(s) of said optionally-substituted 4- to 6-membered saturated aliphatic heterocyclyl group is one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, C1-3alkyl group, hydroxy group, and carboxyl group), and optionally-substituted 5- to 10-membered heteroaryl group (wherein the substituent (s) of said optionally-substituted 5- to 10-membered heteroaryl group is one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, C1-3alkyl group, hydroxy group, and carboxyl group), or

the (ii) optionally-substituted C1-3alkyl group may be any one of the groups of formulae (4)-(6),

in formula (4), m is 1, R7is amino acid group (which binds to C(O) at its N terminus),

in formula (5), q is 1, 2, 3, 4, or 5, L2is single bond or C(O), R8is hydroxy group or amino acid group (which binds to L2at its N terminus),

in formula (6), L3is C(O), R9is hydroxy group or amino acid group (which binds to L3at its N terminus);

R2is hydrogen atom; and

Ring A is a group of formula (2′) or (3′),

when Ring A is a group of formula (2′), R3is hydrogen atom or methyl group, the part of XYZ is N═C—N or NCH3—C═C,

when Ring A is a group of formula (3′), R3is hydrogen atom or methyl group, the part of XYZ is NCH3—C═C or O—C═C.

Term 26

The compound of any one of Terms 2, 18-25 or a pharmaceutically acceptable salt thereof, wherein

R1is, hydrogen atom, or the group of formula (6),

in formula (6), L3is C(O), R9is amino acid group (which binds to L3at its N terminus);

R2is hydrogen atom; and

Ring A is a group of formula (2′) or (3′),

when Ring A is a group of formula (2′), R3is hydrogen atom or methyl group, the part of XYZ is N═C—N or NCH3—C═C,

when Ring A is a group of formula (3′), R3is hydrogen atom or methyl group, the part of XYZ is NCH3—C═C or O—C═C.

Term 27

The compound of Term 1 or 2 or a pharmaceutically acceptable salt thereof which is represented by formula (7):


wherein

Ring B is a group of formula (8), (9), or (10);

R1is

(i) hydrogen atom,

(ii) C1-3alkyl groupwhich may be substituted with one or more substituents selected independently from the group consisting of hydroxy group, methoxy group, ethoxy group, carboxyl group, carbamoyl group (which may be substituted with one or two the same or different C1-3alkyl), NR5R6(wherein R5and R6are independently hydrogen atom, C1-3alkyl group, carboxylmethyl group, 2-hydroxyethyl group, or 2-aminoethyl group), 3- to 6-membered cycloalkyl group (which may be substituted with one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, C1-3alkyl group, hydroxy group, and carboxyl group), 4- to 6-membered saturated aliphatic heterocyclyl group (which may be substituted with one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, C1-3alkyl group, hydroxy group, and carboxyl group), and 5- to 10-membered heteroaryl group (which may be substituted with one or more substituents selected independently from the group consisting of amino group which may be substituted with one or two the same or different C1-3alkyl, C1-3alkyl group, hydroxy group, and carboxyl group),

(iii) the group of formula (4):



wherein m is 1, 2, 3, 4, or 5, R7is C1-3alkoxy group, amino acid group (which binds to C(O) at its N terminus), and peptide consisting of 2-3 amino acid residues (which binds to C(O) at its N terminus),

(iv) the group of formula (5):
R8-L2-(CH2CH2O)qCH2CH2(5)

wherein q is 1, 2, 3, 4, or 5, L2is single bond or C(O), R8is hydroxy group, C1-3alkoxy group, amino group which may be substituted with one or two the same or different C1-3alkyl, amino acid group (which binds to L2at its N terminus), or peptide consisting of 2-3 amino acid residues (which binds to L2at its N terminus), or

(v) the group of formula (6):



wherein L3is CH2or C(O), and R9is hydroxy group, C1-3alkoxy group, amino group which may be substituted with one or two the same or different C1-3alkyl, amino acid group (which binds to L3at its N terminus), or peptide consisting of 2-3 amino acid residues (which binds to L3at its N terminus);

X1is O or NR14; and

R13and R14are independently hydrogen atom, C1-3alkyl group, or 3- to 6-membered cycloalkyl group.

Term 28

The compound of Term 27 or a pharmaceutically acceptable salt thereof, wherein Ring B is the group of formula (8).

Term 29

The compound of Term 27 or 28 or a pharmaceutically acceptable salt thereof, wherein R1is the group of formula (4), (5), or (6).

Term 30

The compound of any one of Terms 27-29 or a pharmaceutically acceptable salt thereof, wherein L2and L3are C(O).

Term 31

The compound of any one of Terms 27-29 or a pharmaceutically acceptable salt thereof, wherein R1is the group of formula (4).

Term 32

The compound of any one of Terms 27-30 or a pharmaceutically acceptable salt thereof, wherein R1is the group of formula (6).

Term 33

The compound of any one of Terms 27-32 or a pharmaceutically acceptable salt thereof, wherein R7, R8, or R9is amino acid group (which binds to C(O), L2, or L3at its N terminus).

Term 34

The compound of any one of Terms 27-33 or a pharmaceutically acceptable salt thereof, wherein R7, R8, or R9is L-glutamic acid (which binds to C(O), L2, or L3at its N terminus).

Term 35

The compound of any one of Terms 27-34 or a pharmaceutically acceptable salt thereof, wherein R13is hydrogen atom.

Term 36

The compound of any one of Terms 27-35 or a pharmaceutically acceptable salt thereof, wherein X1is NR14.

Term 37

The compound of any one of Terms 27-36 or a pharmaceutically acceptable salt thereof wherein R14is methyl group.

Term 38

The compound of Term 1 or 2 or a pharmaceutically acceptable salt thereof, which is selected from the following compounds:3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromene-5-carboxylic acid (Example 1),prop-2-yn-1-yl 3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromene-5-carboxylate (Example 2),N-({4-[({[3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)methyl]-1H-1,2,3-triazol-1-yl}acetyl)-L-glutamic acid (Example 3),N2-({4-[({[3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)methyl]-1H-1,2,3-triazol-1-yl}acetyl)-L-arginine (Example 4),N-{[3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}-L-glutamic acid (Example 5),3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-N-(prop-2-yn-1-yl)-4H-chromene-5-carboxamide (Example 6),3-(6,7-dihydroxy-1,2-dimethyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromene-5-carboxylic acid (Example 7),N-({4-[({[3-(6,7-dihydroxy-1,2-dimethyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)methyl]-1H-1,2,3-triazol-1-yl}acetyl)-L-glutamic acid (Example 8),6,6′,7,7′-tetrahydroxy-2,4′-dioxo-2H,4′H-3,3′-bichromene-5′-carboxylic acid (Example 9),prop-2-yn-1-yl 6,6′,7,7′-tetrahydroxy-2,4′-dioxo-2H,4′H-3,3′-bichromene-5′-carboxylate (Example 10),N-{[4-({[(6,6′,7,7′-tetrahydroxy-2,4′-dioxo-2H,4′H-3,3′-bichromen-5′-yl)carbonyl]oxy}methyl)-1H-1,2,3-triazol-1-yl]acetyl}-L-glutamic acid (Example 11),N2-{[4-({[(6,6′,7,7′-tetrahydroxy-2,4′-dioxo-2H,4′H-3,3′-bichromen-5′-yl)carbonyl]oxy}methyl)-1H-1,2,3-triazol-1-yl]acetyl}-L-arginine (Example 12),3-(6,7-dihydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromene-5-carboxylic acid (Example 13),N-({4-[({[3-(6,7-dihydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)methyl]-1H-1,2,3-triazol-1-yl}acetyl)-L-glutamic acid (Example 14),N-({4-[({[3-(6,7-dihydroxy-1,4-dimethyl-2-oxo-1,2-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)methyl]-1H-1,2,3-triazol-1-yl}acetyl)-L-glutamic acid (Example 15),3-(7,8-dihydroxy-2-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromene-5-carboxylic acid (Example 16),N-({4-[({[3-(7,8-dihydroxy-2-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)methyl]-1H-1,2,3-triazol-1-yl}acetyl)-L-glutamic acid (Example 17),N-[({[3-(7,8-dihydroxy-2-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)acetyl]-L-glutamic acid (Example 18),N-[({[3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)acetyl]-L-glutamic acid (Example 19),3-[2-({[3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)ethoxy]propanoic acid (Example 20),N-{3-[2-({[3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)ethoxy]propanoyl}-L-glutamic acid (Example 21),2,2′-{[2-({[3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)ethyl]imino}-diacetic acid (Example 22),2,3-dihydroxypropyl 3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromene-5-carboxylate (Example 23),(trans-4-aminocyclohexyl)methyl 3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromene-5-carboxylate (Example 24),(1,4-dimethylpiperazin-2-yl)methyl 3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromene-5-carboxylate (Example 25),(1-methyl-1H-imidazol-2-yl)methyl 3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromene-5-carboxylate (Example 26),0-{[3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}-L-homoserine (Example 27),2-(3-hydroxypyrrolidin-1-yl)ethyl 3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromene-5-carboxylate (Example 28),14-hydroxy-3,6,9,12-tetraoxatetradec-1-yl 3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromene-5-carboxylate (Example 29), and2-amino-2-oxoethyl 3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromene-5-carboxylate (Example 30).
Term 39

The compound of Term 1 or 2 or a pharmaceutically acceptable salt thereof, which is selected from the following compounds:3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromene-5-carboxylic acid (Example 1),prop-2-yn-1-yl 3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromene-5-carboxylate (Example 2),N-({4-[({[3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)methyl]-1H-1,2,3-triazol-1-yl}acetyl)-L-glutamic acid (Example 3),N2-({4-[({[3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)methyl]-1H-1,2,3-triazol-1-yl}acetyl)-L-arginine (Example 4),N-{[3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}-L-glutamic acid (Example 5),3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-N-(prop-2-yn-1-yl)-4H-chromene-5-carboxamide (Example 6),3-(6,7-dihydroxy-1,2-dimethyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromene-5-carboxylic acid (Example 7),N-({4-[({[3-(6,7-dihydroxy-1,2-dimethyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)methyl]-1H-1,2,3-triazol-1-yl}acetyl)-L-glutamic acid (Example 8),6,6′,7,7′-tetrahydroxy-2,4′-dioxo-2H,4′H-3,3′-bichromene-5′-carboxylic acid (Example 9),prop-2-yn-1-yl 6,6′,7,7′-tetrahydroxy-2,4′-dioxo-2H,4′H-3,3′-bichromene-5′-carboxylate (Example 10),N-{[4-({[(6,6′,7,7′-tetrahydroxy-2,4′-dioxo-2H,4′H-3,3′-bichromen-5′-yl)carbonyl]oxy}methyl)-1H-1,2,3-triazol-1-yl]acetyl}-L-glutamic acid (Example 11),N2-{[4-({[(6,6′,7,7′-tetrahydroxy-2,4′-dioxo-2H,4′H-3,3′-bichromen-5′-yl)carbonyl]oxy}methyl)-1H-1,2,3-triazol-1-yl]acetyl}-L-arginine (Example 12),3-(6,7-dihydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromene-5-carboxylic acid (Example 13),N-({4-[({[3-(6,7-dihydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)methyl]-1H-1,2,3-triazol-1-yl}acetyl)-L-glutamic acid (Example 14),N-({4-[({[3-(6,7-dihydroxy-1,4-dimethyl-2-oxo-1,2-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)methyl]-1H-1,2,3-triazol-1-yl}acetyl)-L-glutamic acid (Example 15),3-(7,8-dihydroxy-2-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromene-5-carboxylic acid (Example 16),N-({4-[({[3-(7,8-dihydroxy-2-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)methyl]-1H-1,2,3-triazol-1-yl}acetyl)-L-glutamic acid (Example 17),N-[({[3-(7,8-dihydroxy-2-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)acetyl]-L-glutamic acid (Example 18), andN-[({[3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)acetyl]-L-glutamic acid (Example 19).
Term 40

The compound of Term 1 or 2 or a pharmaceutically acceptable salt thereof, which is selected from thefollowing compounds:3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromene-5-carboxylic acid (Example 1),N-({4-[({[3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)methyl]-1H-1,2,3-triazol-1-yl}acetyl)-L-glutamic acid (Example 3),N2-({4-[({[3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)methyl]-1H-1,2,3-triazol-1-yl}acetyl)-L-arginine (Example 4),N-{[3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}-L-glutamic acid (Example 5),3-(6,7-dihydroxy-1,2-dimethyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromene-5-carboxylic acid (Example 7),N-({4-[({[3-(6,7-dihydroxy-1,2-dimethyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)methyl]-1H-1,2,3-triazol-1-yl}acetyl)-L-glutamic acid (Example 8),6,6′,7,7′-tetrahydroxy-2,4′-dioxo-2H,4′H-3,3′-bichromene-5′-carboxylic acid (Example 9),N-{[4-({[(6,6′,7,7′-tetrahydroxy-2,4′-dioxo-2H,4′H-3,3′-bichromen-5′-yl)carbonyl]oxy}methyl)-1H-1,2,3-triazol-1-yl]acetyl}-L-glutamic acid (Example 11),N2-{[4-({[(6,6′,7,7′-tetrahydroxy-2,4′-dioxo-2H,4′H-3,3′-bichromen-5′-yl)carbonyl]oxy}methyl)-1H-1,2,3-triazol-1-yl]acetyl}-L-arginine (Example 12),3-(6,7-dihydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromene-5-carboxylic acid (Example 13),N-({4-[({[3-(6,7-dihydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)methyl]-1H-1,2,3-triazol-1-yl}acetyl)-L-glutamic acid (Example 14),N-({4-[({[3-(6,7-dihydroxy-1,4-dimethyl-2-oxo-1,2-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)methyl]-1H-1,2,3-triazol-1-yl}acetyl)-L-glutamic acid (Example 15),3-(7,8-dihydroxy-2-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromene-5-carboxylic acid (Example 16),N-({4-[({[3-(7,8-dihydroxy-2-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)methyl]-1H-1,2,3-triazol-1-yl}acetyl)-L-glutamic acid (Example 17),N-[({[3-(7,8-dihydroxy-2-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)acetyl]-L-glutamic acid (Example 18), andN-[({[3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)acetyl]-L-glutamic acid (Example 19).
Term 41

The compound of Term 1 or 2 or a pharmaceutically acceptable salt thereof, which is selected from the following compounds:3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromene-5-carboxylic acid (Example 1),prop-2-yn-1-yl 3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromene-5-carboxylate (Example 2),N-({4-[({[3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)methyl]-1H-1,2,3-triazol-1-yl}acetyl)-L-glutamic acid (Example 3),N2-({4-[({[3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)methyl]-1H-1,2,3-triazol-1-yl}acetyl)-L-arginine (Example 4),N-{[3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}-L-glutamic acid (Example 5),3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-N-(prop-2-yn-1-yl)-4H-chromene-5-carboxamide (Example 6),3-(6,7-dihydroxy-1,2-dimethyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromene-5-carboxylic acid (Example 7),N-({4-[({[3-(6,7-dihydroxy-1,2-dimethyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)methyl]-1H-1,2,3-triazol-1-yl}acetyl)-L-glutamic acid (Example 8),3-(7,8-dihydroxy-2-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromene-5-carboxylic acid (Example 16),N-({4-[({[3-(7,8-dihydroxy-2-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)methyl]-1H-1,2,3-triazol-1-yl}acetyl)-L-glutamic acid (Example 17),N-[({[3-(7,8-dihydroxy-2-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)acetyl]-L-glutamic acid (Example 18),N-[({[3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)acetyl]-L-glutamic acid (Example 19),3-[2-({[3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)ethoxy]propanoic acid (Example 20),N-{3-[2-({[3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)ethoxy]propanoyl}-L-glutamic acid (Example 21),2,2′-{[2-({[3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)ethyl]imino}-diacetic acid (Example 22),2,3-dihydroxypropyl 3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromene-5-carboxylate (Example 23),(trans-4-aminocyclohexyl)methyl 3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromene-5-carboxylate (Example 24),(1,4-dimethylpiperazin-2-yl)methyl 3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromene-5-carboxylate (Example 25),(1-methyl-1H-imidazol-2-yl)methyl 3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromene-5-carboxylate (Example 26),O-{[3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}-L-homoserine (Example 27),2-(3-hydroxypyrrolidin-1-yl)ethyl 3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromene-5-carboxylate (Example 28),14-hydroxy-3,6,9,12-tetraoxatetradec-1-yl 3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromene-5-carboxylate (Example 29), and2-amino-2-oxoethyl 3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromene-5-carboxylate (Example 30).
Term 42

The compound of Term 1 or 2 or a pharmaceutically acceptable salt thereof, which is selected from the following compounds:3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromene-5-carboxylic acid (Example 1),prop-2-yn-1-yl 3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromene-5-carboxylate (Example 2),N-({4-[({[3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)methyl]-1H-1,2,3-triazol-1-yl}acetyl)-L-glutamic acid (Example 3),N2-({4-[({[3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)methyl]-1H-1,2,3-triazol-1-yl}acetyl)-L-arginine (Example 4),N-{[3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}-L-glutamic acid (Example 5),3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-N-(prop-2-yn-1-yl)-4H-chromene-5-carboxamide (Example 6),3-(6,7-dihydroxy-1,2-dimethyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromene-5-carboxylic acid (Example 7),N-({4-[({[3-(6,7-dihydroxy-1,2-dimethyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)methyl]-1H-1,2,3-triazol-1-yl}acetyl)-L-glutamic acid (Example 8),3-(7,8-dihydroxy-2-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromene-5-carboxylic acid (Example 16),N-({4-[({[3-(7,8-dihydroxy-2-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)methyl]-1H-1,2,3-triazol-1-yl}acetyl)-L-glutamic acid (Example 17),N-[({[3-(7,8-dihydroxy-2-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)acetyl]-L-glutamic acid (Example 18), andN-[({[3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)acetyl]-L-glutamic acid (Example 19).
Term 43

The compound of Term 1 or 2 or a pharmaceutically acceptable salt thereof, which is selected from the following compounds:3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromene-5-carboxylic acid (Example 1),N-({4-[({[3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)methyl]-1H-1,2,3-triazol-1-yl}acetyl)-L-glutamic acid (Example 3),N2-({4-[({[3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)methyl]-1H-1,2,3-triazol-1-yl}acetyl)-L-arginine (Example 4),N-{[3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}-L-glutamic acid (Example 5),3-(6,7-dihydroxy-1,2-dimethyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromene-5-carboxylic acid (Example 7),N-({4-[({[3-(6,7-dihydroxy-1,2-dimethyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)methyl]-1H-1,2,3-triazol-1-yl}acetyl)-L-glutamic acid (Example 8),3-(7,8-dihydroxy-2-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromene-5-carboxylic acid (Example 16),N-({4-[({[3-(7,8-dihydroxy-2-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)methyl]-1H-1,2,3-triazol-1-yl}acetyl)-L-glutamic acid (Example 17),N-[({[3-(7,8-dihydroxy-2-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)acetyl]-L-glutamic acid (Example 18), andN-[({[3-(6,7-dihydroxy-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)acetyl]-L-glutamic acid (Example 19).
Term 44

The compound of Term 1 or 2 or a pharmaceutically acceptable salt thereof, which is selected from thefollowing compounds:6,6′,7,7′-tetrahydroxy-2,4′-dioxo-2H,4′H-3,3′-bichromene-5′-carboxylic acid (Example 9),prop-2-yn-1-yl 6,6′,7,7′-tetrahydroxy-2,4′-dioxo-2H,4′H-3,3′-bichromene-5′-carboxylate (Example 10),N-{[4-({[(6,6′,7,7′-tetrahydroxy-2,4′-dioxo-2H,4′H-3,3′-bichromen-5′-yl)carbonyl]oxy}methyl)-1H-1,2,3-triazol-1-yl]acetyl}-L-glutamic acid (Example 11),N2-{[4-({[(6,6′,7,7′-tetrahydroxy-2,4′-dioxo-2H,4′H-3,3′-bichromen-5′-yl)carbonyl]oxy}methyl)-1H-1,2,3-triazol-1-yl]acetyl}-L-arginine (Example 12),3-(6,7-dihydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromene-5-carboxylic acid (Example 13),N-({4-[({[3-(6,7-dihydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)methyl]-1H-1,2,3-triazol-1-yl}acetyl)-L-glutamic acid (Example 14), andN-({4-[({[3-(6,7-dihydroxy-1,4-dimethyl-2-oxo-1,2-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)methyl]-1H-1,2,3-triazol-1-yl}acetyl)-L-glutamic acid (Example 15).
Term 45

The compound of Term 1 or 2 or a pharmaceutically acceptable salt thereof, which is selected from the following compounds:6,6′,7,7′-tetrahydroxy-2,4′-dioxo-2H,4′H-3,3′-bichromene-5′-carboxylic acid (Example 9),N-{[4-({[(6,6′,7,7′-tetrahydroxy-2,4′-dioxo-2H, 4′H-3,3′-bichromen-5′-yl)carbonyl]oxy}methyl)-1H-1,2,3-triazol-1-yl]acetyl}-L-glutamic acid (Example 11),N2-{[4-({[(6,6′,7,7′-tetrahydroxy-2,4′-dioxo-2H,4′H-3,3′-bichromen-5′-yl)carbonyl]oxy}methyl)-1H-1,2,3-triazol-1-yl]acetyl}-L-arginine (Example 12),3-(6,7-dihydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromene-5-carboxylic acid (Example 13),N-({4-[({[3-(6,7-dihydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)methyl]-1H-1,2,3-triazol-1-yl}acetyl)-L-glutamic acid (Example 14), andN-({4-[({[3-(6,7-dihydroxy-1,4-dimethyl-2-oxo-1,2-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]carbonyl}oxy)methyl]-1H-1,2,3-triazol-1-yl}acetyl)-L-glutamic acid (Example 15).
Term 46

A pharmaceutical composition comprising the compound of any one of Terms 1-45 or a pharmaceutically acceptable salt thereof.

Term 47

A semaphorin inhibitor comprising the compound of any one of Terms 1-45 or a pharmaceutically acceptable salt thereof as an active ingredient.

Term 48

The semaphorin inhibitor of Term 47, wherein the semaphorin is class 3 semaphorins.

Term 49

The semaphorin inhibitor of Term 48, wherein the class 3 semaphorins is semaphorin 3A.

Term 50

An inhibitor for a nerve outgrowth repelling factor comprising the compound of any one of Terms 1-45 or a pharmaceutically acceptable salt thereof as an active ingredient.

Term 51

A medicament having suppressing action on the growth cone collapse activity and/or suppressing action on the nerve outgrowth inhibitory activity in a collagen gel, comprising the compound of any one of Terms 1-45 or a pharmaceutically acceptable salt thereof as an active ingredient.

Term 52

A nerve regeneration promoter comprising the compound of any one of Terms 1-45 or a pharmaceutically acceptable salt thereof as an active ingredient.

Term 53

A medicament for treating and/or preventing a disease associated with neurodegeneration or neurological disorder, comprising the compound of any one of Terms 1-45 or a pharmaceutically acceptable salt thereof as an active ingredient.

Term 54

A medicament for treating and/or preventing a neurological disease associated with ischemic damage, comprising the compound of any one of Terms 1-45 or a pharmaceutically acceptable salt thereof as an active ingredient.

Term 55

The medicament of Term 54, wherein the neurological disease associated with ischemic damage is retinal neurological disorder caused by ischemia or ischemic cerebrovascular disease.

Term 56

The medicament of Term 55, wherein the retinal neurological disorder is glaucoma, central retinal artery occlusion, central branch retinal artery occlusion, central retinal vein occlusion, central branch retinal vein occlusion, ischemic optic neuropathy, diabetic retinopathy, macular degeneration, or retinopathy of prematurity.

Term 57

The medicament of Term 55, wherein the ischemic cerebrovascular disease is cerebral emboli, transient cerebral ischemia, subclavian steal syndrome, Wallenberg's syndrome (lateral medullary syndrome), cerebral thrombosis, lacunar infarct, reversible ischemic neurological deficit, cerebral infarct, moyamoya disease (spontaneous occlusion of the circle of Willis), cerebral hypoxia, sinus thrombosis, or postoperative spinal cord ischemia.

Term 58

A medicament for treating and/or preventing corneal disease, comprising the compound of any one of Terms 1-45 or a pharmaceutically acceptable salt thereof as an active ingredient.

Term 59

The medicament of Term 58, wherein the corneal disease is dry eye, keratitis, leukoma, corneal infection, corneal degeneration, corneal dystrophy, corneal stromal dystrophy, bullous keratopathy, keratoconus, corneal endothelial decompensation, corneal ulcer, nerve-paralytic keratopathy, diabetic keratopathy, chemical ocular injury or corneal burn.

Term 60

The medicament of Term 59, wherein the corneal disease is dry eye, keratitis, bullous keratopathy, corneal ulcer, nerve-paralytic keratopathy, or diabetic keratopathy.

Term 61

The medicament of Term 59, wherein the corneal disease is dry eye.

Term 62

The medicament of any one of Terms 58-61, wherein the corneal disease is a disease associated with neurodegeneration or neurological disorder.

Term 63

A medicament for treating and/or preventing a disease associated with degeneration and damage in central nerve and peripheral nerve, comprising the compound of any one of Terms 1-45 or a pharmaceutically acceptable salt thereof as an active ingredient.

Term 64

A medicament for treating and/or preventing dysosmia, traumatic neurological disorder, cerebral-infarct neurological disorder, facial palsy, diabetic neurosis, glaucoma, retinitis pigmentosa, dry eye, Alzheimer's disease, Parkinson's disease, neurodegenerative disease, muscular dysgenic lateral sclerosis, amyotrophic lateral sclerosis, Huntington's disease, cerebral infarct, or traumatic neurodegenerative disease, comprising the compound of any one of Terms 1-45 or a pharmaceutically acceptable salt thereof as an active ingredient.

Term 65

A medicament for treating and/or preventing dry eye, comprising the compound of any one of Terms 1-45 or a pharmaceutically acceptable salt thereof as an active ingredient.

Term 66

A method for treating and/or preventing a disease associated with neurodegeneration or neurological disorder, comprising administering a therapeutically effective amount of the compound of any one of Terms 1-45 or a pharmaceutically acceptable salt thereof to a patient in need thereof.

Term 67

A method for treating and/or preventing a neurological disease associated with ischemic damage, comprising administering a therapeutically effective amount of the compound of any one of Terms 1-45 or a pharmaceutically acceptable salt thereof to a patient in need thereof.

Term 68

The method of Term 67, wherein the neurological disease associated with ischemic damage is retinal neurological disorder caused by ischemia or ischemic cerebrovascular disease.

Term 69

The method of Term 68, wherein the retinal neurological disorder is glaucoma, central retinal artery occlusion, central branch retinal artery occlusion, central retinal vein occlusion, central branch retinal vein occlusion, ischemic optic neuropathy, diabetic retinopathy, macular degeneration, or retinopathy of prematurity.

Term 70

The method of Term 68, wherein the ischemic cerebrovascular disease is cerebral emboli, transient cerebral ischemia, subclavian steal syndrome, Wallenberg's syndrome (lateral medullary syndrome), cerebral thrombosis, lacunar infarct, reversible ischemic neurological deficit, cerebral infarct, moyamoya disease (spontaneous occlusion of the circle of Willis), cerebral hypoxia, sinus thrombosis, or postoperative spinal cord ischemia.

Term 71

A method for treating and/or preventing corneal disease, comprising administering a therapeutically effective amount of the compound of any one of Terms 1-45 or a pharmaceutically acceptable salt thereof to a patient in need thereof.

Term 72

The method of Term 71, wherein the corneal disease is dry eye, keratitis, leukoma, corneal infection, corneal degeneration, corneal dystrophy, corneal stromal dystrophy, bullous keratopathy, keratoconus, corneal endothelial decompensation, corneal ulcer, nerve-paralytic keratopathy, diabetic keratopathy, chemical ocular injury, or corneal burn.

Term 73

The method of Term 72, wherein the corneal disease is dry eye, keratitis, bullous keratopathy, corneal ulcer, nerve-paralytic keratopathy, or diabetic keratopathy.

Term 74

The method of Term 72, wherein the corneal disease is dry eye.

Term 75

The method of any one of Terms 71-74, wherein the corneal disease is a disease associated with neurodegeneration or neurological disorder.

Term 76

A method for treating and/or preventing a disease associated with degeneration and damage in central nerve and peripheral nerve, comprising administering a therapeutically effective amount of the compound of any one of Terms 1-45 or a pharmaceutically acceptable salt thereof to a patient in need thereof.

Term 77

A method for treating and/or preventing dysosmia, traumatic neurological disorder, cerebral-infarct neurological disorder, facial palsy, diabetic neurosis, glaucoma, retinitis pigmentosa, dry eye, Alzheimer's disease, Parkinson's disease, neurodegenerative disease, muscular dysgenic lateral sclerosis, amyotrophic lateral sclerosis, Huntington's disease, cerebral infarct, or traumatic neurodegenerative disease, comprising administering a therapeutically effective amount of the compound of any one of Terms 1-45 or a pharmaceutically acceptable salt thereof to a patient in need thereof.

Term 78

A method for treating and/or preventing dry eye, comprising administering a therapeutically effective amount of the compound of any one of Terms 1-45 or a pharmaceutically acceptable salt thereof to a patient in need thereof.

Term 79

Use of the compound of any one of Terms 1-45 or a pharmaceutically acceptable salt thereof, in the preparation of a medicament for treating and/or preventing a disease associated with neurodegeneration or neurological disorder.

Term 80

Use of the compound of any one of Terms 1-45 or a pharmaceutically acceptable salt thereof, in the preparation of a medicament for treating and/or preventing a neurological disease associated with ischemic damage.

Term 81

The use of Term 80, wherein the neurological disease associated with ischemic damage is retinal neurological disorder caused by ischemia, or ischemic cerebrovascular disease.

Term 82

The use of Term 81, wherein the retinal neurological disorder is glaucoma, central retinal artery occlusion, central branch retinal artery occlusion, central retinal vein occlusion, central branch retinal vein occlusion, ischemic optic neuropathy, diabetic retinopathy, macular degeneration, or retinopathy of prematurity.

Term 83

The use of Term 81, wherein the ischemic cerebrovascular disease is cerebral emboli, transient cerebral ischemia, subclavian steal syndrome, Wallenberg's syndrome (lateral medullary syndrome), cerebral thrombosis, lacunar infarct, reversible ischemic neurological deficit, cerebral infarct, moyamoya disease (spontaneous occlusion of the circle of Willis), cerebral hypoxia, sinus thrombosis, or postoperative spinal cord ischemia.

Term 84

Use of the compound of any one of Terms 1-45 or a pharmaceutically acceptable salt thereof, in the preparation of a medicament for treating and/or preventing corneal disease.

Term 85

The use of Term 84, wherein the corneal disease is dry eye, keratitis, leukoma, corneal infection, corneal degeneration, corneal dystrophy, corneal stromal dystrophy, bullous keratopathy, keratoconus, corneal endothelial decompensation, corneal ulcer, nerve-paralytic keratopathy, diabetic keratopathy, chemical ocular injury, or corneal burn.

Term 86

The use of Term 85, wherein the corneal disease is dry eye, keratitis, bullous keratopathy, corneal ulcer, nerve-paralytic keratopathy, or diabetic keratopathy.

Term 87

The use of Term 85, wherein the corneal disease is dry eye.

Term 88

The use of any one of Terms 84-87, wherein the corneal disease is a disease associated with neurodegeneration or neurological disorder.

Term 89

Use of the compound of any one of Terms 1-45 or a pharmaceutically acceptable salt thereof, in the preparation of a medicament for treating and/or preventing a disease associated with degeneration and damage in central nerve and peripheral nerve.

Term 90

Use of the compound of any one of Terms 1-45 or a pharmaceutically acceptable salt thereof, in the preparation of a medicament for treating or preventing dysosmia, traumatic neurological disorder, cerebral-infarct neurological disorder, facial palsy, diabetic neurosis, glaucoma, retinitis pigmentosa, dry eye, Alzheimer's disease, Parkinson's disease, neurodegenerative disease, muscular dysgenic lateral sclerosis, amyotrophic lateral sclerosis, Huntington's disease, cerebral infarct, or traumatic neurodegenerative disease.

Term 91

Use of the compound of any one of Terms 1-45 or a pharmaceutically acceptable salt thereof, in the preparation of a medicament for treating and/or preventing dry eye.

Term 92

The compound of any one of Terms 1-45 or a pharmaceutically acceptable salt thereof, in use for treating and/or preventing a disease associated with neurodegeneration or neurological disorder.

Term 93

The compound of any one of Terms 1-45 or a pharmaceutically acceptable salt thereof, in use for treating and/or preventing a neurological disease associated with ischemic damage.

Term 94

The medicament of Term 93, wherein the neurological disease associated with ischemic damage is retinal neurological disorder caused by ischemia or ischemic cerebrovascular disease.

Term 95

The compound of Term 94 or a pharmaceutically acceptable salt thereof, wherein the retinal neurological disorder is glaucoma, central retinal artery occlusion, central branch retinal artery occlusion, central retinal vein occlusion, central branch retinal vein occlusion, ischemic optic neuropathy, diabetic retinopathy, macular degeneration, or retinopathy of prematurity.

Term 96

The compound of Term 94 or a pharmaceutically acceptable salt thereof, wherein the ischemic cerebrovascular disease is cerebral emboli, transient cerebral ischemia, subclavian steal syndrome, Wallenberg's syndrome (lateral medullary syndrome), cerebral thrombosis, lacunar infarct, reversible ischemic neurological deficit, cerebral infarct, moyamoya disease (spontaneous occlusion of the circle of Willis), cerebral hypoxia, sinus thrombosis, or postoperative spinal cord ischemia.

Term 97

The compound of any one of Terms 1-45 or a pharmaceutically acceptable salt thereof, in use for treating and/or preventing corneal disease.

Term 98

The compound of Term 97 or a pharmaceutically acceptable salt thereof, wherein the corneal disease is dry eye, keratitis, leukoma, corneal infection, corneal degeneration, corneal dystrophy, corneal stromal dystrophy, bullous keratopathy, keratoconus, corneal endothelial decompensation, corneal ulcer, nerve-paralytic keratopathy, diabetic keratopathy, chemical ocular injury, or corneal burn.

Term 99

The compound of Term 98 or a pharmaceutically acceptable salt thereof, wherein the corneal disease is dry eye, keratitis, bullous keratopathy, corneal ulcer, nerve-paralytic keratopathy, or diabetic keratopathy.

Term 100

The compound of Term 98 or a pharmaceutically acceptable salt thereof, wherein the corneal disease is dry eye.

Term 101

The compound of any one of Terms 97-100 or a pharmaceutically acceptable salt thereof, wherein the corneal disease is a disease associated with neurodegeneration or neurological disorder.

Term 102

The compound of any one of Terms 1-45 or a pharmaceutically acceptable salt thereof, in use for treating and/or preventing a disease associated with degeneration and damage in central nerve and peripheral nerve.

Term 103

The compound of any one of Terms 1-45 or a pharmaceutically acceptable salt thereof, in use for treating and/or preventing dysosmia, traumatic neurological disorder, cerebral-infarct neurological disorder, facial palsy, diabetic neurosis, glaucoma, retinitis pigmentosa, dry eye, Alzheimer's disease, Parkinson's disease, neurodegenerative disease, muscular dysgenic lateral sclerosis, amyotrophic lateral sclerosis, Huntington's disease, cerebral infarct, or traumatic neurodegenerative disease.

Term 104

The compound of any one of Terms 1-45 or a pharmaceutically acceptable salt thereof, in use for treating and/or preventing dry eye.

Effect of Invention

The present invention provides the compound of formula (1) or a pharmaceutically acceptable salt thereof. The compound or a pharmaceutically acceptable salt thereof has a semaphorin inhibitory activity and it is useful as a medicament for treating or preventing neuropathic disease, neurodegenerative disease, neurological disease associated with ischemic deficit, and corneal disease.

