Biheterocyclic compound
The present invention provides a compound of formula (1) and a pharmaceutical composition comprising the compound useful as a nerve regeneration promoter wherein R 1 -L- is R 1 —OC(O)—, or the like, R 1 is hydrogen atom, optionally-substituted C 1-6 alkyl group, optionally-substituted 3- to 8-membered cycloalkyl group, or the like, R 2 is hydrogen atom or the like, Ring A is formula (2) or formula (3) wherein R 3 is hydrogen atom, optionally-substituted C 1-6 alkyl group, or the like, the part of X, Y, and Z is X═Y—Z, X—Y═Z, or X—Y—Z, X is nitrogen atom, NR 4 (R 4 is hydrogen atom, optionally-substituted C 1-6 alkyl group, or the like), or the like, Y is carbon atom or the like, and Z is carbon atom, nitrogen atom or the like.
1. A compound of formula (1):
or a pharmaceutically acceptable salt thereof
wherein
R 1 -L- is R 1 —OC(O)— or R 1 —NHC(O)—;
R 1 is
(i) hydrogen atom,
(ii) optionally-substituted C 1-6 alkyl group,
(iii) optionally-substituted C 2-6 alkenyl group,
(iv) optionally-substituted C 2-6 alkynyl 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;
R 2 is hydrogen atom, hydroxy group, or carboxyl group; and
Ring A is a group of formula (2) or (3):
wherein R 3 is
(i) hydrogen atom,
(ii) optionally-substituted C 1-6 alkyl group,
(iii) optionally-substituted C 2-6 alkenyl group,
(iv) optionally-substituted C 2-6 alkynyl 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 is X═Y—Z, X—Y═Z, or X—Y—Z,
X is nitrogen atom, NR 4 , or oxygen atom, provided that X is not oxygen atom in the case of formula (2),
R 4 is
(i) hydrogen atom,
(ii) optionally-substituted C 1-6 alkyl group,
(iii) optionally-substituted C 2-6 alkenyl group,
(iv) optionally-substituted C 2-6 alkynyl 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.
2. The compound of claim 1 or a pharmaceutically acceptable salt thereof, which is represented by formula (1′):
wherein
R 1 -L- is R 1 —OC(O)— or R 1 —NHC(O)—;
R 1 is
(i) hydrogen atom,
(ii) optionally-substituted C 1-6 alkyl group,
(iii) optionally-substituted C 2-6 alkenyl group,
(iv) optionally-substituted C 2-6 alkynyl 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 C 1-6 alkyl 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 C 1-3 alkyl), NR 5 R 6 (wherein R 5 and R 6 are independently hydrogen atom, C 1-3 alkyl 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 C 1-3 alkyl, C 1-3 alkyl 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 C 1-3 alkyl, C 1-3 alkyl 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 C 1-3 alkyl, C 1-3 alkyl group, hydroxy group, and carboxyl group), or
the (ii) optionally-substituted C 1-6 alkyl group may be any one of the following groups of formulae (4)-(6):
formula (4):
wherein m is 1, 2, 3, 4, or 5, R 7 is C 1-3 alkoxy 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):
R 8 -L 2 -(CH 2 CH 2 O) q CH 2 CH 2 → (5)
wherein q is 1, 2, 3, 4, or 5, L 2 is single bond or C(O), R 8 is hydroxy group, C 1-3 alkoxy group, amino group which may be substituted with one or two the same or different C 1-3 alkyl, amino acid group (which binds to L 2 at its N terminus), or peptide consisting of 2-3 amino acid residues (which binds to L 2 at its N terminus),
formula (6):
wherein L 3 is CH 2 or C(O), and R 9 is hydroxy group, C 1-3 alkoxy group, amino group which may be substituted with one or two the same or different C 1-3 alkyl, amino acid group (which binds to L 3 at its N terminus), or peptide consisting of 2-3 amino acid residues (which binds to L 3 at its N terminus),
the substituent(s) of the (iii) optionally-substituted C 2-6 alkenyl group, and the (iv) optionally-substituted C 2-6 alkynyl 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 C 1-3 alkyl), NR 5 R 6 (wherein R 5 and R 6 are independently hydrogen atom, C 1-3 alkyl 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 C 1-3 alkyl, 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 C 1-3 alkyl, C 1-3 alkyl 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 C 1-3 alkyl, and carboxyl group;
R 2 is hydrogen atom, hydroxy group, or carboxyl group; and
Ring A is a group of formula (2′) or (3′):
wherein R 3 is
(i) hydrogen atom,
(ii) optionally-substituted C 1-6 alkyl group,
(iii) optionally-substituted C 2-6 alkenyl group,
(iv) optionally-substituted C 2-6 alkynyl 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 C 1-6 alkyl group, the (iii) optionally-substituted C 2-6 alkenyl group, the (iv) optionally-substituted C 2-6 alkynyl 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 C 1-3 alkyl, and amino group which may be substituted with one or two the same or different C 1-3 alkyl,
the part of is X═Y—Z, X—Y═Z, or X—Y—Z,
X is nitrogen atom, NR 4 , or oxygen atom, provided that X is not oxygen atom in the case of formula (2′),
R 4 is
(i) hydrogen atom,
(ii) optionally-substituted C 1-6 alkyl group,
(iii) optionally-substituted C 2-6 alkenyl group,
(iv) optionally-substituted C 2-6 alkynyl 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 C 1-6 alkyl group, the (iii) optionally-substituted C 2-6 alkenyl group, the (iv) optionally-substituted C 2-6 alkynyl 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 C 1-3 alkyl, and amino group which may be substituted with one or two the same or different C 1-3 alkyl,
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.
3. The compound of claim 2 or a pharmaceutically acceptable salt thereof, wherein R 2 is hydrogen atom.
4. The compound of claim 2 or a pharmaceutically acceptable salt thereof, wherein R 3 is (i) hydrogen atom, (ii) C 1-3 alkyl group, or (v) 3- to 6-membered cycloalkyl group.
5. The compound of claim 2 or a pharmaceutically acceptable salt thereof, wherein R 4 is (i) hydrogen atom, (ii) C 1-3 alkyl group, or (v) 3- to 6-membered cycloalkyl group.
6. The compound of claim 2 or a pharmaceutically acceptable salt thereof, wherein
R 1 is (i) hydrogen atom, or (ii) optionally-substituted C 1-6 alkyl group,
wherein the substituent(s) of the (ii) optionally-substituted C 1-6 alkyl 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 C 1-3 alkyl), NR 5 R 6 (wherein R 5 and R 6 are independently hydrogen atom, C 1-3 alkyl 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 C 1-3 alkyl, C 1-3 alkyl 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 C 1-3 alkyl, C 1-3 alkyl 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 C 1-3 alkyl, C 1-3 alkyl group, hydroxy group, and carboxyl group), or
the (ii) optionally-substituted C 1-6 alkyl group may be any one of the groups of formulae (4)-(6).
7. The compound of claim 2 or a pharmaceutically acceptable salt thereof, wherein
R 1 is
(i) hydrogen atom,
(ii) optionally-substituted C 1-3 alkyl group,
(iii) optionally-substituted C 2-4 alkenyl group,
(iv) optionally-substituted C 2-4 alkynyl 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 C 1-3 alkyl 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 C 1-3 alkyl), NR 5 R 6 (wherein R 5 and R 6 are independently hydrogen atom, C 1-3 alkyl 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 C 1-3 alkyl, C 1-3 alkyl 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 C 1-3 alkyl, C 1-3 alkyl 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 C 1-3 alkyl, C 1-3 alkyl group, hydroxy group, and carboxyl group), or
the (ii) optionally-substituted C 1-3 alkyl group may be any one of the groups of formulae (4)-(6),
in formula (4), m is 1, R 7 is amino acid group (which binds to C(O) at its N terminus),
in formula (5), q is 1, 2, 3, 4, or 5, L 2 is single bond or C(O), R 8 is hydroxy group or amino acid group (which binds to L 2 at its N terminus),
in formula (6), L 3 is C(O), R 9 is hydroxy group or amino acid group (which binds to L 3 at its N terminus),
the substituent(s) of the (iii) optionally-substituted C 2-4 alkenyl group, and the (iv) optionally-substituted C 2-4 alkynyl 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 C 1-3 alkyl), NR 5 R 6 (wherein R 5 and R 6 are independently hydrogen atom, C 1-3 alkyl 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 C 1-3 alkyl, 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 C 1-3 alkyl, C 1-3 alkyl 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 C 1-3 alkyl, and carboxyl group.
8. The compound of claim 2 or a pharmaceutically acceptable salt thereof, wherein
R 1 is (i) hydrogen atom, or (ii) optionally-substituted C 1-3 alkyl group,
wherein the substituent(s) of the (ii) optionally-substituted C 1-3 alkyl 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 C 1-3 alkyl), NR 5 R 6 (wherein R 5 and R 6 are independently hydrogen atom, C 1-3 alkyl 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 C 1-3 alkyl, C 1-3 alkyl 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 C 1-3 alkyl, C 1-3 alkyl 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 C 1-3 alkyl, C 1-3 alkyl group, hydroxy group, and carboxyl group), or
the (ii) optionally-substituted C 1-3 alkyl group may be any one of the groups of formulae (4)-(6),
in formula (4), m is 1, R 7 is amino acid group (which binds to C(O) at its N terminus),
in formula (5), q is 1, 2, 3, 4, or 5, L 2 is single bond or C(O), R 8 is hydroxy group or amino acid group (which binds to L 2 at its N terminus),
in formula (6), L 3 is C(O), R 9 is hydroxy group or amino acid group (which binds to L 3 at its N terminus).
9. The compound of claim 2 or a pharmaceutically acceptable salt thereof, wherein
R 1 is hydrogen atom, or the group of formula (6),
in formula (6), L 3 is C(O), R 9 is amino acid group (which binds to L 3 at its N terminus).
10. The compound of claim 2 or a pharmaceutically acceptable salt thereof, wherein Ring A is the group of formula (2′).
11. The compound of claim 10 or a pharmaceutically acceptable salt thereof, wherein the part of in formula (2′) is N═C—CH, N═C—N, NR 4 —C═C, NR 4 —CH—N, or NR 4 —CH—CH.
12. The compound of claim 2 or a pharmaceutically acceptable salt thereof, wherein Ring A is the group of formula (3′).
13. The compound of claim 12 or a pharmaceutically acceptable salt thereof, wherein the part of in formula (3′) is N═C—CH, N═C—N, NR 4 —C═C, NR 4 —CH—N, NR 4 —CH—CH, O—C═C, O—CH—N, or O—CH—CH.
14. The compound of claim 1 or a pharmaceutically acceptable salt thereof which is represented by formula (7):
wherein
Ring B is a group of formula (8), (9), or (10);
R 1 is
(i) hydrogen atom,
(ii) C 1-3 alkyl group
which 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 C 1-3 alkyl), NR 5 R 6 (wherein R 5 and R 6 are independently hydrogen atom, C 1-3 alkyl 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 C 1-3 alkyl, C 1-3 alkyl 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 C 1-3 alkyl, C 1-3 alkyl 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 C 1-3 alkyl, C 1-3 alkyl group, hydroxy group, and carboxyl group),
(iii) the group of formula (4):
wherein m is 1, 2, 3, 4, or 5, R 7 is C 1-3 alkoxy 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):
R 8 -L 2 -(CH 2 CH 2 O) q CH 2 CH 2 → (5)
wherein q is 1, 2, 3, 4, or 5, L 2 is single bond or C(O), R 8 is hydroxy group, C 1-3 alkoxy group, amino group which may be substituted with one or two the same or different C 1-3 alkyl, amino acid group (which binds to L 2 at its N terminus), or peptide consisting of 2-3 amino acid residues (which binds to L 2 at its N terminus), or
(v) the group of formula (6):
wherein L 3 is CH 2 or C(O), and R 9 is hydroxy group, C 1-3 alkoxy group, amino group which may be substituted with one or two the same or different C 1-3 alkyl, amino acid group (which binds to L 3 at its N terminus), or peptide consisting of 2-3 amino acid residues (which binds to L 3 at its N terminus);
X 1 is O or NR 14 ; and
R 13 and R 14 are independently hydrogen atom, C 1-3 alkyl group, or 3- to 6-membered cycloalkyl group.
15. The compound of claim 14 or a pharmaceutically acceptable salt thereof, wherein Ring B is the group of formula (8).
16. The compound of claim 14 or a pharmaceutically acceptable salt thereof, wherein R 1 is the group of formula (4), (5), or (6).
17. The compound of claim 14 or a pharmaceutically acceptable salt thereof, wherein L 2 and L 3 are C(O).
18. The compound of claim 14 or a pharmaceutically acceptable salt thereof wherein R 7 , R 8 , or R 9 is amino acid group (which binds to C(O), L 2 , or L 3 at its N terminus).
19. The compound of claim 14 or a pharmaceutically acceptable salt thereof, wherein R 7 , R 8 , or R 9 is L-glutamic acid (which binds to C(O), L 2 , or L 3 at its N terminus).
20. The compound of claim 1 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,
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,
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,
N 2 -({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,
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,
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,
3-(6,7-dihydroxy-1,2-dimethyl-4-oxo-1,4-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromene-5-carboxylic acid,
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,
6,6′,7,7′-tetrahydroxy-2,4′-dioxo-2H,4′H-3,3′-bichromene-5′-carboxylic acid,
prop-2-yn-1-yl 6,6′,7,7′-tetrahydroxy-2,4′-dioxo-2H,4′H-3,3′-bichromene-5′-carboxylate,
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,
N 2 -{[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,
3-(6,7-dihydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)-6,7-dihydroxy-4-oxo-4H-chromene-5-carboxylic acid,
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,
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,
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,
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,
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,
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,
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,
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,
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,
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,
(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,
(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,
(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,
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,
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,
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, and
2-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.
21. A pharmaceutical composition comprising the compound of claim 1 or a pharmaceutically acceptable salt thereof.
22. A semaphorin inhibitor comprising the compound of claim 1 or a pharmaceutically acceptable salt thereof as an active ingredient.
23. A nerve regeneration promoter comprising the compound of claim 1 or a pharmaceutically acceptable salt thereof as an active ingredient.
24. A medicament for treating and/or preventing a disease associated with neurodegeneration or neurological disorder, comprising the compound of claim 1 or a pharmaceutically acceptable salt thereof as an active ingredient.
25. A medicament for treating and/or preventing a neurological disease associated with ischemic damage, comprising the compound of claim 1 or a pharmaceutically acceptable salt thereof as an active ingredient.
26. A medicament for treating or preventing corneal disease, comprising the compound of claim 1 or a pharmaceutically acceptable salt thereof as an active ingredient.
27. The medicament of claim 26 , wherein the corneal disease is dry eye.
28. The medicament of claim 26 , wherein the corneal disease is a disease associated with neurodegeneration or neurological disorder.