JP2759257B2 - Diabetes treatment - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a therapeutic agent for diabetes.

[0002]

DISCLOSURE OF THE INVENTION The therapeutic agent for diabetes of the present invention has the general formula

[0003]

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[Wherein R ¹ is a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, an amino group which may have a lower alkyl group as a substituent or an aminocarbonyl which may have a lower alkyl group as a substituent. Represents a group. R ² represents a hydrogen atom, a lower alkyl group which may have a halogen atom as a substituent, a phenyl group, a morpholino-substituted lower alkyl group or an imidazolyl-substituted lower alkyl group. n and m each represent 0 or 1. r
Represents 1 or 2. R ³ and R ⁴ are the same or different,
A) hydrogen atom; b) lower alkyl group; c) phenyl lower alkoxycarbonyl group; d) lower alkanoyloxy-substituted lower alkyl group; e) lower alkanoyl group; f) lower alkoxycarbonyl group; g) lower alkoxy lower alkyl group H) phenoxycarbonyl group;
i) lower alkanoyl-substituted lower alkyl; j) lower alkoxycarbonyloxy-substituted lower alkyl; k)
A benzoyl-substituted lower alkyl group which may have a halogen atom as a substituent on the phenyl ring; l) a group -ER
⁵² R ⁵³ (R ⁵² and R ⁵³ are the same or different and are each a hydrogen atom,
It represents a lower alkyl group, a lower alkoxycarbonyl group or a phenyl group. R ⁵² and R ⁵³ may be bonded to each other with or without another nitrogen atom or oxygen atom together with the nitrogen atom to which they are bonded to form a 5- or 6-membered saturated heterocyclic ring. E is a lower alkylene group, a group -C
(= O)-or a group -C (= O) -A- (A is a lower alkylene group). ); M) group

[0005]

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(Wherein A is as defined above; R ⁵⁴ represents a hydrogen atom or a lower alkyl group);

[0007]

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(Wherein A represents a lower alkylene group; p represents an integer of 1 to 3; R ⁵ has a hydrogen atom, a lower alkoxy-substituted lower alkoxy group, a lower alkoxy group, and a lower alkyl group as a substituent; With an amino group, a halogen atom, a nitro group, a hydroxyl group, a lower alkyl group which may have a hydroxyl group as a substituent, a lower alkenyloxy group, a carboxy-substituted lower alkoxy group, a lower alkoxycarbonyl-substituted lower alkoxy group, a lower alkoxycarbonyl group, A halogen atom-substituted lower alkoxy group, a hydroxyl-substituted lower alkoxy group, a phenyl lower alkoxy group which may have a group selected from the group consisting of a lower alkyl group and a lower alkoxy group as a substituent on a phenyl ring, a lower alkyl group as a substituent 1,3-dioxolanyl group which may have Alkanoyl group, a morpholino-substituted lower alkoxy group, a morpholino-substituted lower alkyl group, a morpholinocarbonyl group or a group -Y-A ₁ -CONR ⁶
R ⁷ (where A ₁ represents a lower alkylene group; Y represents a group —O— or a group —NH—; R ⁶ and R ⁷ are the same or different and are a hydrogen atom, a lower group which may have a hydroxyl group as a substituent; An alkyl group, a phenyl lower alkyl group which may have a lower alkoxy group as a substituent on the phenyl ring,
It represents a furyl-substituted lower alkyl group or a lower alkoxy-substituted lower alkyl group. R ⁶ and R ⁷ may form a 5- or 6-membered saturated heterocyclic ring with or without a nitrogen atom or an oxygen atom together with the nitrogen atom to which they are bonded. The heterocycle may have 1 to 3 groups selected from the group consisting of a hydroxyl group, a lower alkyl group and a phenyl lower alkyl group as a substituent. ). O) an amino group or a lower alkoxy-substituted lower group which may have on the phenyl ring a lower alkoxy group or a halogen atom as a substituent, and a group selected from the group consisting of a lower alkanoyl group and a phenyl lower alkenylcarbonyl group as a substituent. An alkoxy group, a tetrazolyl group which may have a lower alkyl group as a substituent on the tetrazole ring, a hydroxyl group, a group -O
_{^{-A 4 -CO-NR 40 R 41}} (A 4 is .R ⁴⁰ and R ⁴¹ represents a lower alkylene group is a hydrogen atom or a lower alkyl group the same or different. The R ⁴⁰ and R ^41, they are bonded May form a 5- or 6-membered saturated heterocyclic ring with or without another nitrogen atom or oxygen atom together with the nitrogen atom to form a 5- or 6-membered saturated heterocyclic ring.), A lower alkenyloxy group, a nitro group and a substituent. A phenyl lower alkenyl group which may have a group selected from the group consisting of a lower alkyl group which may have a halogen atom; p) an alkenyl group; q) a cycloalkyl lower alkyl group; r) a naphthyl lower alkyl group; A phenylthio-substituted lower alkyl group which may have a lower alkoxy group as a substituent on the ring; t) a lower alkoxy group as a substituent on the phenyl ring Phenylsulfonyl-substituted lower alkyl group which may have a u) lower alkoxy group as a substituent on the phenyl ring; is phenylsulfonyl-substituted lower alkyl group v) phenoxy-substituted lower alkyl group; w) group

[0009]

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(Wherein q represents an integer of 1 to 3).

[0011]

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Is a 5- to 14-membered monocyclic, dimeric or ternary saturated or unsaturated heterocyclic ring having 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur. Shows a substituted lower alkyl group. R ⁸ is substituted on the heterocyclic ring, and R ⁸ is a hydrogen atom, an oxo group, a lower alkyl group which may have a hydroxyl group as a substituent, a halogen atom, a nitro group, a lower alkoxy group, a cyano group, a lower alkoxy group. Carbonyl group, phenyl lower alkoxy group which may have an amino group which may have a lower alkanoyl group as a substituent on the phenyl ring, carboxy-substituted lower alkoxy group, carboxy group, lower alkoxycarbonyl-substituted lower alkoxy group, hydroxyl group, lower Alkoxy-substituted lower alkoxy group, lower alkenyloxy group, lower alkanoyloxy-substituted lower alkyl group, halogen atom-substituted lower alkyl group, lower alkanoyl group, lower alkyl group as a substituent on a phenyl ring, lower alkoxy-substituted lower alkoxy group, hydroxyl group, Halogen atom and lower alkyl A phenyl group, which may have a group selected from the group consisting of a coxy group,
A lower alkenyl group, a morpholinocarbonyl lower alkoxy group, a lower alkylsulfinyl group, an amino group-substituted lower alkyl group having a group selected from the group consisting of a lower alkylsulfonyl group and a lower alkanoyl group as a substituent, a lower alkylthio group, a lower Alkylsulfonyl group, lower alkanoyloxy group, 1,3-dioxolanyl-substituted lower alkyl group which may have a lower alkyl group as a substituent, lower alkanoyl group-substituted lower alkyl group, and amino group which may have a lower alkyl group as a substituent Carbonyl-substituted lower alkyl group, lower alkoxycarbonyl group-substituted lower alkenyl group, aminocarbonyl-substituted lower alkenyl group which may have a lower alkyl group as a substituent, carboxy group-substituted lower alkenyl group, benzoyl group, lower Alkoxy-lower alkyl group, a group

[0013]

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(Wherein, s represents an integer of 1 to 3.

[0015]

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Represents a 5- or 6-membered saturated or unsaturated heterocyclic group having 1 to 4 hetero atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom. R ⁴⁵ is substituted on the above heterocyclic ring, and R ⁴⁵ represents a hydrogen atom, a lower alkyl group, a lower alkoxy lower alkyl group, a phenyl group or an oxo group. ), Group

[0017]

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(Where t represents an integer of 1 to 3).

[0019]

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Represents a 5- or 6-membered saturated or unsaturated heterocyclic-substituted lower alkyl group having 1-4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur. R
⁴⁶ is substituted on the above heterocyclic ring, and R ⁴⁶ represents a hydrogen atom, a lower alkyl group or an oxo group. ) Or a group-(C = O)
1NR ⁹ R ¹⁰ (where 1 represents 0 or 1. R ⁹ and R
¹⁰ is the same or different, hydrogen atom, lower alkanoyl group, lower alkyl group, morpholinocarbonyl lower alkyl group, cycloalkylcarbonyl group, phenyl lower alkenylcarbonyl group, lower alkylsulfonyl group, having a lower alkyl group as a substituent A certain aminocarbonyl group, a phenylsulfonyl group which may have a lower alkyl group as a substituent on the phenyl ring, a phenyl lower alkenyl group, a halogen atom as a substituent on the phenyl ring, a lower alkoxy group, a lower alkanoyl group as a substituent. A benzoyl group that may have 1 to 3 groups selected from the group consisting of an amino group and a hydroxyl group that may have
Amino group-substituted lower alkanoyl group which may have a lower alkanoyl group as a substituent, amino group-substituted sulfonyl group which may have a lower alkyl group as a substituent,
A phenyl lower alkyl group, a phenyl group or an amino group which may have a lower alkanoyl group as a substituent. Further, R ⁹ and R ¹⁰ may be bonded to each other via a nitrogen atom to which they are bonded, with or without another nitrogen atom or oxygen atom, to form a 5- or 6-membered saturated heterocyclic ring. ). ); X) group -A ₅ -CR ⁴² R ⁴³
R ⁴⁴ (wherein A ₅ are a lower alkylene group .R ⁴² and R
⁴³ together form a group = O, a group = N-OH or a lower alkylenedioxy group. R ⁴⁴ represents a phenyl group which may have a lower alkoxy group as a substituent on the phenyl ring. Y) 2,3-dihydro-1H
A 2,3-dihydro-1H-indenyl-substituted lower alkyl group which may have on the indenyl ring a group selected from the group consisting of an oxo group as a substituent, a hydroxyl group and a silyloxy group having a lower alkyl group as a substituent; Or z)
Base

[0021]

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(Where u represents an integer of 1 to 3).

[0023]

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Is a 5- to 14-membered mono-, di- or tri-cyclic saturated or unsaturated heterocyclic ring having 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur. Shows a lower alkenyl group. R ⁴⁷ is substituted on the above heterocyclic ring, and R ⁴⁷ is a hydrogen atom, a halogen atom-substituted lower alkyl group, an oxo group, a halogen atom, a lower alkoxy group, a lower alkyl group, a lower alkoxycarbonyl group, a carboxy group, or a lower substituent. It may have an aminocarbonyl group which may have an alkyl group, an amino group which may have a lower alkanoyl group as a substituent, or a group selected from a lower alkoxy group and a halogen atom as a substituent on a phenyl ring. Phenyl group or group

[0025]

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(Wherein A ₆ , R ⁴⁵ and s are as defined above)
Is shown. ). A) R ³ and R ⁴ may be bonded together with the nitrogen atom to which they are bonded to form a 1,2,3,4-tetrahydroisoquinolyl group. The heterocyclic ring may have a lower alkoxy group as a substituent. And at least one compound selected from the group consisting of a quinoxaline derivative represented by the formula (1) and salts thereof as an active ingredient.

Most of the quinoxaline derivatives represented by the above general formula (1) and salts thereof in which n is 0 are novel compounds not described in any literature.

[0028] According to the WHO classification, diabetes is acute or subacute due to a shortage of the absolute amount of insulin, and insulin dependent diabetics requiring insulin treatment.
etes melitus, IDDM), non-insulin-dependent diabetes mellitus that progresses slowly and does not always require insulin treatment
pendent diabetes mellitu
s, NIDDM), malnutrition-related diabetes (malnu)
trition-related diabetes
melitus, MRDM) and other diseases and chronic hyperglycemia associated with the disease state.

[0029] Among them, the cause of IDDM is considered to be due to the destruction of pancreatic β cells by an autoimmune mechanism.
The involvement of HLA antigens and cytokine viruses is considered to be the cause of pancreatic β-cell destruction (Koji Nakanishi, Tetsuro Kobayashi, Mitsuru Hara: “Diabetics 1989”, edited by Kunori Kosaka, Yasuo Akanuma, Diagnosis and Therapeutics) , 1989, 226-244.
page). On the other hand, the causes of NIDDM include (i) congenital abnormalities in the pancreas, ie, abnormalities in adaptability to increased insulin demand, and (ii) impaired insulin action caused by various factors such as aging, obesity, and stress. (Hiroo Imura: “Advances in Diabetes 1989”,
Vol.23, Diabetes Society of Japan, Diagnosis and Therapeutics, 1989
Year, p. 1-12).

However, the onset of diabetes is caused by IDDM, NI
Genetic factors and environmental factors, including DDM, are intricately intertwined, leaving much to be known.

Here, when looking at tissues in NIDDM, two important causes of hyperglycemia are reduced sugar uptake in peripheral tissues, particularly muscle tissues, and enhanced sugar release in the liver. It is considered. Currently, the most commonly used pharmacotherapy is insulin or a sulfonylurea agent (insulin secretagogue), which is basically based on supplementing the deficient insulin, but strict blood glucose control is difficult. And may cause high insulin plasma and hypoglycemia. Therefore, compounds that promote glucose uptake in muscle tissue without promoting insulin secretion become high insulin plasma and a new type of hypoglycemic agent without fear of hypoglycemia, and are useful as therapeutic agents for diabetes. Conceivable.

The quinoxaline derivative represented by the general formula (1) and a salt thereof (hereinafter, referred to as "the compound of the present invention")
L is a cell line of rat striated muscle (muscle cells).
It promotes the uptake of 2-deoxyglucose (2DG) into 6 cells, promotes the consumption of glucose, and exhibits a blood glucose lowering effect. It also promotes sugar uptake in muscle tissue. In particular, the compound of the present invention can be used for db / db mice and KK-Ay mice (L. Herbe)
rg, D.E. L. Coleman; Metabolis
m, Vol. 26, No. 1, January, 1977, 59-9
9) and the like. In addition, since the compound of the present invention does not act on insulin secretion or glucose release in the liver, it does not have a rapid blood glucose lowering effect, and OGTT (o
ral glucose tolerance tes
It has desirable features that hardly affect t).

Therefore, the therapeutic agent for diabetes of the present invention is useful as a therapeutic agent for diabetes and diabetic vascular disorders, diabetic retinopathy, diabetic nephropathy, diabetic complications such as diabetic neuropathy and the like.

Each group represented by the above general formula (1) is more specifically as follows.

The lower alkyl group includes, for example, methyl,
Ethyl, propyl, isopropyl, butyl, tert-
Examples thereof include linear or branched alkyl groups having 1 to 6 carbon atoms such as butyl, pentyl and hexyl groups.

Examples of the halogen atom include a fluorine atom,
Examples include a chlorine atom, a bromine atom and an iodine atom.

The lower alkyl group which may have a halogen atom as a substituent includes, for example, trifluoromethyl, trichloromethyl,
Chloromethyl, bromomethyl, fluoromethyl, iodomethyl, difluoromethyl, dibromomethyl, 2-chloroethyl, 2,2,2-trifluoroethyl, 2,2
2-trichloroeryl, 3-chloropropyl, 2,3-
Dichloropropyl, 4,4,4-trichlorobutyl, 4
-Fluorobutyl, 5-chloropentyl, 3-chloro-
C1-C6 which may have 1-3 halogen atoms as a substituent, such as 2-methylpropyl, 5-bromohexyl, 5,6-dichlorohexyl, 5-bromohexyl, and 5,6-dichlorohexyl group. A straight-chain or branched-chain alkyl group.

As the morpholino-substituted lower alkyl group,
For example, morpholinomethyl, 2-morpholinoethyl, 1-
Morpholinoethyl, 3- (2-morpholinyl) propyl, 4- (3-morpholinyl) butyl, 1,1-dimethyl-2- (2-morpholinyl) ethyl, 5-morpholinopentyl, 6-morpholinohexyl, 2-methyl- 3-
The alkyl moiety such as a morpholinopropyl group has 1 to 6 carbon atoms
And a morpholino-substituted alkyl group which is a linear or branched alkyl group.

Examples of the imidazolyl-substituted lower alkyl group include (1-imidazolyl) methyl, 2- (1-imidazolyl) ethyl, 1- (2-imidazolyl) ethyl, 3- (4-imidazolyl) propyl and 4- (5 -Imidazolyl) butyl, 1,1-dimethyl-2- (2-imidazolyl) ethyl, 5- (4-imidazolyl) pentyl, 6- (1-imidazolyl) hexyl, 2-methyl-
Examples thereof include an imidazolyl-substituted alkyl group in which the alkyl moiety such as a 3- (1-imidazolyl) propyl group is a linear or branched alkyl group having 1 to 6 carbon atoms.

As the lower alkylene group, for example, methylene, ethylene, trimethylene, 2-methyltrimethylene, 2,2-dimethyltrimethylene, 1-methyltrimethylene, methylmethylene, ethylmethylene, tetramethylene, pentamethylene, hexamethylene C1 of group etc.
To 6 linear or branched alkylene groups.

Examples of the lower alkoxy group include linear or branched alkoxy groups having 1 to 6 carbon atoms, such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, tert-butoxy, pentyloxy and hexyloxy groups. it can.

Examples of the amino group which may have a lower alkyl group as a substituent include, for example, amino, methylamino, ethylamino, propylamino, isopropylamino, butylamino, tert-butylamino, pentylamino, hexylamino, dimethyl Amino, diethylamino, dipropylamino, dibutylamino, dipentylamino, dihexylamino, N-methyl-N-ethylamino, N-ethyl-N-propylamino, N-methyl-
Examples of the substituent such as N-butylamino and N-methyl-N-hexylamino group include an amino group which may have 1 to 2 carbon atoms having 1 to 6 linear or branched alkyl groups.

The lower alkyl group which may have a hydroxyl group as a substituent includes, for example, hydroxymethyl, 2-hydroxyethyl, 1-
Hydroxyethyl, 1-hydroxyisopropyl, 3-
Hydroxypropyl, 2,3-dihydroxypropyl,
4-hydroxybutyl, 1,1-dimethyl-2-hydroxyethyl, 5,5,4-trihydroxypentyl, 5
-Hydroxypentyl, 6-hydroxyhexyl, 2-
A straight-chain having 1 to 6 carbon atoms which may have 1 to 3 hydroxyl groups as a substituent such as methyl-3-hydroxypropyl, 2,3-dihydroxyethyl, 3,4-dihydroxybutyl, and 5,6-dihydroxyhexyl. A chain or branched alkyl group can be exemplified.

Examples of the lower alkenyloxy group include allyloxy, 2-butenyloxy, 3-butenyloxy, 1-methylallyloxy, 2-pentenyloxy,
A linear or branched alkenyloxy group having 2 to 6 carbon atoms such as a 2-hexenyloxy group can be exemplified.

Examples of the carboxy-substituted lower alkoxy group include carboxymethoxy, 2-carboxyethoxy, 1-carboxyethoxy, 3-carboxypropoxy, 4-carboxybutoxy, 5-carboxypentyloxy, 6-carboxyhexyloxy, , 1-dimethyl-2-carboxyethoxy, 2-methyl-3-carboxypropoxy, etc., when the alkoxy moiety has 1 carbon atom.
And carboxyalkoxy groups, which are straight-chain or branched-chain alkoxy groups of 1 to 6.

The lower alkoxy group substituted with lower alkoxycarbonyl group includes, for example, methoxycarbonylmethoxy, 3-methoxycarbonylpropoxy, ethoxycarbonylmethoxy, 3-ethoxycarbonylpropoxy,
4-ethoxycarbonylbutoxy, 5-isopropoxycarbonylpentyloxy, 6-propoxycarbonylhexyloxy, 1,1-dimethyl-2-butoxycarbonylethoxy, 2-methyl-3-tert-butoxycarbonylpropoxy, 2-pentyloxycarbonyl A straight-chain or branched-chain alkoxycarbonyl group having 1 to 6 carbon atoms in which an alkoxycarbonyl moiety such as an ethoxy or hexyloxycarbonylmethoxy group is a straight-chain or branched-chain alkoxycarbonyl group having 1 to 6 carbon atoms. be able to.

Examples of the lower alkoxycarbonyl group include linear groups having 1 to 6 carbon atoms such as methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, tert-butoxycarbonyl, pentyloxycarbonyl and hexyloxycarbonyl. Alternatively, a branched alkoxycarbonyl group can be exemplified.

Examples of the halogen atom-substituted lower alkoxy group include trifluoromethoxy, trichloromethoxy, chloromethoxy, bromomethoxy, fluoromethoxy, iodomethoxy, difluoromethoxy, dibromomethoxy, 2-chloroethoxy, 2,2,2- Trifluoroethoxy, 2,2,2-trichloroethoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 4,
4,4-trichlorobutoxy, 4-fluorobutoxy,
5-chloropentyloxy, 3-chloro-2-methylpropoxy, 5-bromohexyloxy, 5,6-dichlorohexyloxy, 5-bromohexyloxy, 5,6
Examples of the substituent such as -dichlorohexyloxy group include a linear or branched alkoxy group having 1 to 3 halogen atoms and 1 to 6 carbon atoms.

Examples of the hydroxy-substituted lower alkoxy group include hydroxymethoxy, 2-hydroxyethoxy, 1-hydroxyethoxy, 1-hydroxypropoxy, 3-hydroxypropoxy, 2,3-dihydroxypropoxy, 4-hydroxybutoxy, 1-dimethyl-2-hydroxyethoxy, 5,5,4-trihydroxypentyloxy, 5-hydroxypentyloxy, 6-hydroxyhexyloxy, 1-hydroxyisopropoxy, 2-methyl-3-hydroxypropoxy, 2,3 1 to 6 carbon atoms having 1 to 3 hydroxyl groups as substituents such as dihydroxyethoxy, 3,4-dihydroxybutoxy, and 5,6-dihydroxyhexyloxy groups;
And a straight-chain or branched-chain alkoxy group.

The phenyl lower alkoxy group which may have a substituent selected from the group consisting of a lower alkyl group and a lower alkoxy group on the phenyl ring includes, for example, benzyloxy, 2-phenylethoxy, 1-phenylethoxy, 3-phenylpropoxy, 4-phenylbutoxy, 1,1-dimethyl-2-phenylethoxy, 5-
Phenylpentyloxy, 6-phenylhexyloxy, 2-methyl-3-phenylpropoxy, 2- (3-
Methoxyphenyl) ethoxy, 1- (4-methoxyphenyl) ethoxy, 2-methoxybenzyloxy, 3-
(2-ethoxyphenyl) propoxy, 4- (3-ethoxyphenyl) butoxy, 1,1-dimethyl-2- (4
-Ethoxyphenyl) ethoxy, 5- (4-isopropoxyphenyl) pentyloxy, 6- (4-hexyloxyphenyl) hexyloxy, 3,4-dimethoxybenzyloxy, 3,4,5-trimethoxybenzyloxy, , 5-Dimethoxybenzyloxy, 3-methoxybenzyloxy, 4-methoxybenzyloxy, 2,4
-Diethoxybenzyloxy, 2,3-dimethoxybenzyloxy, 2,4-dimethoxybenzyloxy, 2,
6-dimethoxybenzyloxy, 2-methylbenzyloxy, 4-ethylbenzyloxy, 2- (3-methylphenyl) ethoxy, 1- (4-methylphenyl) ethoxy, 3- (2-ethylphenyl) propoquin, 4- (3
-Ethylphenyl) butoxy, 1,1-dimethyl-2-
(4-ethylphenyl) ethoxy, 5- (4-isopropylphenyl) pentyloxy, 6- (4-hexylphenyl) hexyloxy, 3,4-dimethylbenzyloxy, 3,4,5-trimethylbenzyloxy, 2, 5
An alkoxy moiety such as -dimethylbenzyloxy or 2-methoxy-3-methylbenzyloxy group has 1 to 6 carbon atoms;
And a straight-chain or branched-chain alkoxy group having 1 to 6 carbon atoms and a straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms on the phenyl ring. And a phenylalkoxy group which may have 1 to 3 groups selected from the group.

Examples of the 1,3-dioxolanyl group which may have a lower alkyl group as a substituent include, for example,
1,3-dioxolanyl, 2-methyl-1,3-dioxolanyl, 4-ethyl-1,3-dioxolanyl, 2-
Propyl-1,3-dioxolanyl, 4-butyl-1,
3-dioxolanyl, 2-pentyl-1,3-dioxolanyl, 4-hexyl-1,3-dioxolanyl, 2,
4-dimethyl-1,3-dioxolanyl, 2,4,5-
As a substituent such as a trimethyl-1,3-dioxolanyl group, a linear or branched alkyl group having 1 to 6 carbon atoms may be used.
1,3-dioxolanyl groups which may be present.

Examples of the lower alkanoyl group include linear or branched alkanoyl groups having 1 to 6 carbon atoms, such as formyl, acetyl, propionyl, butyryl, isobutyryl, pentanoyl, tert-butylcarbonyl and hexanoyl groups.

Examples of the morpholino-substituted lower alkoxy group include morpholinomethoxy, 2-morpholinoethoxy, 1-morpholinoethoxy, 3- (2-morpholinyl) propoxy, 4- (3-morpholinyl) butoxy,
Alkoxy moieties such as 1,1-dimethyl-2- (2-morpholinyl) ethoxy, 5-morpholinopentyloxy, 6-morpholinohexyloxy, and 2-methyl-3-morpholinopropoxy have a straight-chain structure having 1 to 6 carbon atoms. A morpholino-substituted alkoxy group which is a branched alkoxy group can be exemplified.

Examples of the phenyl lower alkyl group include benzyl, 2-phenylethyl, 1-phenylethyl,
An alkyl moiety such as 3-phenylpropyl, 4-phenylbutyl, 5-phenylpentyl, 6-phenylhexyl, 1,1-dimethyl-2-phenylethyl, or 2-methyl-3-phenylpropyl has 1 to 6 carbon atoms. And a phenylalkyl group which is a linear or branched alkyl group.

The phenyl lower alkyl group which may have a lower alkoxy group as a substituent on the phenyl ring includes, in addition to the phenyl lower alkyl group, 2- (3-
Methoxyphenyl) ethyl, 1- (4-methoxyphenyl) ethyl, 2-methoxybenzyl, 3-methoxybenzyl, 4-methoxybenzyl, 3- (2-ethoxyphenyl) propyl, 4- (3-ethoxyphenyl) butyl, 1,1-dimethyl-2- (4-ethoxyphenyl)
Ethyl, 5- (4-isopropoxyphenyl) pentyl, 6- (4-hexyloxyphenyl) hexyl,
A linear or branched alkyl group having 1 to 6 carbon atoms in the alkyl moiety such as 3,4-dimethoxybenzyl, 2,4-dimethoxybenzyl, 3,4,5-trimethoxybenzyl, and phenyl Examples thereof include a phenylalkyl group which may have 1 to 3 linear or branched alkoxy groups having 1 to 6 carbon atoms on the ring.

Examples of the furyl-substituted lower alkyl group include (2-furyl) methyl, 2- (3-furyl) ethyl,
1- (2-furyl) ethyl, 3- (2-furyl) propyl, 4- (3-furyl) butyl, 5- (2-furyl) pentyl, 6- (3-furyl) hexyl, 1,1-dimethyl -2- (2-furyl) ethyl, 2-methyl-3- (3
An alkyl moiety such as -furyl) propyl group has 1 to 6 carbon atoms
And a furyl-substituted alkyl group which is a linear or branched alkyl group.

The lower alkoxy lower alkyl group includes:
For example, methoxymethyl, 2-ethoxyethyl, 1-methoxyethyl, 3-methoxypropyl, 4-ethoxybutyl, 6-propoxyhexyl, 5-isopropoxypentyl, 1,1-dimethyl-2-butoxyethyl, 2-methyl- Alkyl moiety such as 3-tert-butoxypropyl, 2-pentyloxyethyl, hexyloxymethyl group is a straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms. A chain alkoxyalkyl group can be exemplified.

An amino group or a lower alkoxy group substituted with a lower alkoxy group or a halogen atom which may have a substituent selected from the group consisting of a lower alkanoyl group and a phenyl lower alkenylcarbonyl group as a substituent on a phenyl ring; group, tetrazolyl group, hydroxyl group, group ^{_{-O-a 4 -CO-NR 40}} R 41 (a 4 which may have lower alkyl group as a substituent on the tetrazole ring,
R ⁴⁰ and R ⁴¹ are the same as above. ), A lower alkenyloxy group, a nitro group and a phenyl lower alkenyl group which may have a group selected from the group consisting of a lower alkyl group which may have a halogen atom as a substituent include, for example, styryl, cinnamyl, 4-phenyl -3-butenyl,
4-phenyl-2-butenyl, 5-phenyl-4-pentenyl, 5-phenyl-3-pentenyl, 5-phenyl-2-pentenyl, 6-phenyl-5-hexenyl, 6
-Phenyl-4-hexenyl, 6-phenyl-3-hexenyl, 6-phenyl-2-hexenyl, β-methyl-
4-phenyl-3-butenyl, β-methyl-cinnamyl, γ-methyl-cinnamyl, 5-phenyl-2,4-
Pentadienyl, 4-phenyl-1,3-butadienyl, 6-phenyl-2,4-hexadienyl, 6-phenyl-3,5-hexadienyl, 6-phenyl-1,3
-Hexadienyl, 5-phenyl-1,3-pentadienyl, 3-methoxycinnamyl, 4-methoxycinnamyl, 2-methoxycinnamyl, 4-methoxystyryl,
(2-ethoxyphenyl) -2-butenyl, 5- (3-
Ethoxyphenyl) -4-pentenyl, α, α-dimethyl-4-ethoxycinnamyl, 5- (4-isopropoxyphenyl) -2,4-pentadienyl, 6- (4-hexyloxyphenyl) -2-hexenyl, 3,4-dimethoxycinnamyl, 3,4,5-trimethoxystyryl, 2,5-dimethoxystyryl, 3-methoxystyryl, 4-methoxystyryl, 2,4-diethoxystyryl, 2,3-dimethoxycinnamyl , 2,4-dimethoxycinnamyl, 2,6-dimethoxycinnamyl, 2-nitrocinnamyl, 3-nitrocinnamyl, 4-nitrocinnamyl, 4- (2-nitrophenyl) -3-butenyl, 4- (3-nitrophenyl) -2-butenyl, 5-
(2-nitrophenyl) -2-pentenyl, 6- (3-
Nitrophenyl) -3-hexenyl, 3,4-dinitrocinnamyl, 3,4,5-trinitrocinnamyl, 2-
Nitrostyryl, 3-nitrostyryl, 4-nitrostyryl, 3-methylcinnamyl, 2-methylstyryl,
-Methylcinnamyl, 2-ethylcinnamyl, 4-isopropylcinnamyl, 4- (3-ethylphenyl) -3
-Butenyl, α-methyl-4-isopropylcinnamyl, 5- (4-isopropylphenyl) -2-pentenyl, 6- (4-hexylphenyl) -2-hexenyl,
3,4-dimethylcinnamyl, 3,4,5-trimethylcinnamyl, 2,5-dimethylcinnamyl, 2-chlorocinnamyl, 3-chlorostyryl, 2-fluorocinnamyl, 4-chlorocinnamyl, -Fluorostyryl,
4- (3-fluorophenyl) -2-butenyl, 5-
(4-fluorophenyl) -2-pentel, α, α-dimethyl-2-bromocinnamyl, 6- (3-bromophenyl) -2-hexenyl, 4-bromostyryl, 2-iodophenylcinnamyl, 3-iodostyryl , 3,4
-Dichlorocinnamyl, 3,5-dichlorocinnamyl,
2,6-dichlorostyryl, 2,3-dichlorocinnamyl, 2,4-dichlorostyryl, 3,4-difluorocinnamyl, 3,5-dibromocinnamyl, 3,4,5-
Trichlorocinnamyl, 2-methoxy-3-chlorocinnamyl, 3- (4-acetylaminophenyl) -2-butenyl, 3- (2-trifluoromethylphenyl) -2
-Butenyl, 3- [4- (1-methyltetrazole-5
-Yl) phenyl] -2-butenyl, 3- (4-cinnamoylaminophenyl) -2-butenyl, 3- (3-methoxymethoxyphenyl) -2-butenyl, 3- (2-
Methoxyphenyl) -2-butenyl, 3- (3-methoxyphenyl) -2-butenyl, 3- (4-trifluoromethylphenyl) -2-butenyl, 3- (3-trifluoromethylphenyl) -2-butenyl , 3- (3-acetylaminophenyl) -2-butenyl, 3- (3-hydroxyphenyl) -2-butenyl, 3- (3-morpholinocarbonylmethoxyphenyl) -2-butenyl, 3-
(3-diethylaminocarbonylmethoxyphenyl)-
2-butenyl, 3- [3- (2-methyl-2-propenyloxy) phenyl] -2-butenyl, 4-chloromethylstyryl, 3-bromomethylcinnamyl, 4- (2-
Iodomethylphenyl) -3-butenyl, 4- [4-
(2,2,2-trichloroethyl) phenyl] -2-butenyl, 5- (4-aminophenyl) -4-pentenyl, 5- (3-propionylaminophenyl) -2-pentenyl, 6- (2-butenyl Rylaminophenyl) -5-
Hexenyl, 6- (4-pentanoylaminophenyl)
-4-hexenyl, 6- (3-hexanoylaminophenyl) -3-hexenyl, 6- (2,4-diaminophenyl) -2-hexenyl, 2,4,6-triaminocinnamyl, 4- (3 -Butenoylamino) styryl, 3-
(2-pentenoylamino) cinnamyl, 4- [2-
(4-hexenoylamino) phenyl] -3-butenyl, 4- [4- (4-ethoxybutoxy) phenyl]-
2-butenyl, 3- [4- (N-acetyl-N-cinnamoylamino) phenyl] -2-butenyl, 5- [2-
(6-propoxyhexyloxy) phenyl] -4-pentenyl, 5- [3- (2-pentyloxyethoxy)
Phenyl] -2-pentenyl, 6- (4-hexyloxymethoxyphenyl) -5-hexenyl, 6- [2-
(1,1-dimethyl-2-butoxyethoxy) phenyl] -3-hexenyl, 3- (2,4-dimethoxymethoxyphenyl) -2-butenyl, 3- (2,4,6-trimethoxymethoxyphenyl)- 2-butenyl, 3-
[4- (1-ethyltetrazol-5-yl) phenyl] -2-butenyl, 3- [3- (2-propyltetrazol-5-yl) phenyl] -2-butenyl, 3-
[2- (1-butyltetrazol-5-yl) phenyl] -2-butenyl, 3- [4- (2-pentyltetrazol-5-yl) phenyl] -2-butenyl, 3-
[3- (1-hexyltetrazol-5-yl) phenyl] -2-butenyl, 2-hydroxycinnamyl, 3-
Hydroxycinnamyl, 4-hydroxycinnamyl, 4
-(2-hydroxyphenyl) -3-butenyl, 5-
(2-hydroxyphenyl) -2-pentenyl, 6-
(3-hydroxyphenyl) -3-hexenyl, 2,4
-Dihydroxycinnamyl, 3,4,5-trihydroxycinnamyl, 4-hydroxystyryl, 4-allyloxystyryl, 3- (2-butenyloxy) cinnamyl, 4- [2- (3-butenyloxy) phenyl] -3
-Butenyl, 5- [3- (2-pentenyloxy) phenyl] -2-pentenyl, 6- [4- (2-hexenyloxy) phenyl] -4-hexenyl, 2,4-diallyloxycinnamyl, 2, 4,6-triallyloxystyryl, 3- (2-dimethylaminocarbonylethoxyphenyl) -2-butenyl, 4- [4- (3-butylaminocarbonylpropoxy) phenyl] -3-butenyl, 5- [2- (4-pentylaminocarbonylbutoxy) phenyl] -3-pentenyl, 6- [3- (5-hexylaminocarbonylpentyloxy) phenyl]-
5-hexenyl, 4- [6- (N-methyl-N-propylamino) carbonylhexyloxy] styryl, 4-
Methylaminocarbonylmethoxycinnamyl, 4- (1
-Piperidinyl) carbonylmethoxycinnamyl, 3-
(1-piperazinyl) carbonylmethoxystyryl, 4
-[3- (1-pyrrolidinyl) carbonylmethoxyphenyl] -3-butenyl, 3- (2-methoxy-5-chlorophenyl) -2-butenyl, 3- (2-methoxymethoxy-5-chlorophenyl) -2-butenyl , 3- (2
Alkenyl group having 1 to 2 straight or branched double bonds having 2 to 6 carbon atoms in the alkenyl moiety such as -hydroxy-5-chlorophenyl) -2-butenyl group; A straight-chain or branched alkoxy group having 1 to 6 carbon atoms, a halogen atom, a straight-chain or branched alkanoyl group having 1 to 6 carbon atoms as a substituent and an alkenylcarbonyl moiety An amino group which may have 1 to 2 groups selected from the group consisting of a phenylalkenylcarbonyl group which is a chain or branched alkenylcarbonyl group, and a linear or branched alkoxy group having 1 to 6 carbon atoms A linear or branched alkoxy group having 1 to 6 carbon atoms, a tetrazolyl group which may have a linear or branched alkyl group having 1 to 6 carbon atoms as a substituent on the tetrazole ring, a hydroxyl group, a group- OA _{^{4 -CO-NR 40 R 41 (}} A 4 is a straight-chain or .R ⁴⁰ and R ⁴¹ show a branched chain alkylene group are the same or different and each represents a hydrogen atom or a straight-1 to 6 carbon atoms having 1 to 6 carbon atoms A chain or branched alkyl group, and R ⁴⁰ and R ⁴¹
May be bonded to each other with or without another nitrogen atom or oxygen atom together with the nitrogen atom to which they are bonded to form a 5- or 6-membered saturated heterocyclic ring. ), A linear or branched alkenyloxy group having 2 to 6 carbon atoms, a nitro group and a linear or branched alkyl having 1 to 6 carbon atoms which may have 1 to 3 halogen atoms as a substituent. A phenylalkenyl group which may have 1 to 3 groups selected from the group consisting of groups can be mentioned.

Examples of the alkenyl group include vinyl, allyl, 3-methyl-2-butenyl, 2-butenyl,
Butenyl, 1-methylallyl, 2-pentenyl, 2-hexenyl, 1-heptenyl, 1-octenyl, 1-nonenyl, 1-decenyl, 1-undecenyl, 1-dodecenyl, 2-heptenyl, 3-heptenyl, 2-methyl- 4
-Heptenyl, 2-methyl-5-heptenyl, 4-methyl-2-heptenyl, 3-methyl-1-heptenyl,
1,3-heptadienyl, 1,4-heptadienyl,
1,5-heptadienyl, 1,6-heptadienyl,
2,4-heptadienyl, 2-methyl-2,4-heptadienyl, 2,6-dimethyl-2,4-heptadienyl, 2,5-dimethyl-1,3-heptadienyl, 2,
4,6-trimethyl-2,4-heptadienyl, 2-octenyl, 3-octenyl, 4-octenyl, 2-methyl-5-octenyl, 2-methyl-6-octenyl, 2
-Methyl-7-octenyl, 1,3-octadienyl,
1,4-octadienyl, 1,5-octadienyl,
1,6-octadienyl, 1,7-octadienyl,
2,4-octadienyl, 3,7-octadienyl,
4,8-dimethyl-3,7-octadienyl, 2,4,
6-trimethyl-3,7-octadienyl, 3,4-dimethyl-2,5-octadienyl, 3,7-dimethyl-
2,6-octadienyl, 4,8-dimethyl-2,6-
Octadienyl, 2-nonenyl, 3-nonenyl, 4-nonenyl, 2-methyl-5-nonenyl, 2-methyl-6
Nonenyl, 2-methyl-7-nonenyl, 2-methyl-8
-Nonenyl, 1,3-nonadienyl, 1,4-nonadienyl, 1,5-nonadienyl, 1,6-nonadienyl,
1,7-nonadienyl, 1,8-nonadienyl, 2,4
-Nonadienyl, 3,7-nonadienyl, 4,8-dimethyl-3,7-nonadienyl, 2,4,6-trimethyl-3,7-nonadienyl, 3,4-dimethyl-2,5-
Nonadienyl, 4,8-dimethyl-2,6-nonadienyl, 2-decenyl, 3-decenyl, 4-decenyl, 5-
Decenyl, 2-methyl-6-decenyl, 3-methyl-7
-Decenyl, 4-methyl-8-decenyl, 5-methyl-
9-decenyl, 1,3-decadienyl, 1,4-decadienyl, 1,5-decadienyl, 1,6-decadienyl, 1,7-decadinyl, 1,8-decadienyl, 1,
9-decadienyl, 2-methyl-2,4-decadienyl, 3-methyl-2,5-decadienyl, 4,8-dimethyl-2,6-decadienyl, 2,4,6-trimethyl-3,7-decadienyl, 2,9-dimethyl-3,7-
Decadienyl, 2-undecenyl, 3-undecenyl,
4-undecenyl, 5-undecenyl, 2-methyl-6
-Undecenyl, 3-methyl-7-undecenyl, 4-
Methyl-8-undecenyl, 5-methyl-9-undecenyl, 2-methyl-10-undecenyl, 1,3-undecadienyl, 1,4-undecadienyl, 1,5-undecadienyl, 1,6-undecadienyl, 1,7-
Undecadienyl, 1,8-Undecadienyl, 1,9
-Undecadienyl, 1,10-undecadienyl, 2
-Methyl-2,4-undecadienyl, 3-methyl-
2,5-undecadienyl, 4,8-dimethyl-2,6
-Undecadienyl, 2,4,6-trimethyl-3,8
-Undecadienyl, 2,9-dimethyl-3,8-undecadienyl, 2-dodecenyl, 3-dodecenyl, 4-
Dodecenyl, 5-dodecenyl, 6-dodecenyl, 2-methyl-7-dodecenyl, 3-methyl-8-dodecenyl,
4-methyl-9-dodecenyl, 5-methyl-10-dodecenyl, 6-methyl-11-dodecenyl, 2-methyl-
2,4-dodecadienenyl, 3-methyl-2,5-dodecadienenyl, 4,8-dimethyl-2,6-dodecadienenyl, 2,4,6-trimethyl-2,7-dodecadienenyl, 2,10-dimethyl-2, 8-dodecadienyl,
2,5-dimethyl-3,7-dodecadienyl, 4,8,
12-trimethyl-3,7,11-dodecatrienyl,
1,3,5-heptatrienyl, 2,4,6-octatrienyl, 1,3,6-nonatrienyl, 2,6,8-
A linear or branched double bond having 2 to 12 carbon atoms such as dodecatrienyl and 1,5,7-undecatrienyl
An alkenyl group having three can be exemplified.

As the cycloalkyl lower alkyl group,
For example, cyclohexylmethyl, 2-cyclopropylethyl, 1-cyclobutylethyl, 3-cyclopentylpropyl, 4-cyclohexylbutyl, 2,2-dimethyl-3-cycloheptylpropyl, 5-cyclooctylpentyl, 6-cyclohexylhexyl group And the like can be exemplified by a C3-C8 cycloalkylalkyl group in which the alkyl moiety is a C1-C6 linear or branched alkyl group.

Examples of the naphthyl lower alkyl group include α-naphthylmethyl, β-naphthylmethyl,
(Α-naphthyl) ethyl, 1- (β-naphthyl) ethyl, 3- (β-naphthyl) propyl, 4- (α-naphthyl) butyl, 2-methyl-3- (α-naphthyl) propyl, 5- ( The alkyl moiety such as β-naphthyl) pentyl, 6- (α-naphthyl) hexyl and 1,1-dimethyl-2- (β-naphthyl) ethyl is a linear or branched alkyl group having 1 to 6 carbon atoms. A certain naphthylalkyl group can be exemplified.

The phenylthio-substituted lower alkyl group which may have a lower alkoxy group as a substituent on the phenyl ring includes, for example, phenylthiomethyl, 2-phenylthioethyl, 1-phenylthioethyl, 3-phenylthiopropyl, 4-phenylthiobutyl, 5-phenylthiopentyl, 6-phenylthiohexyl, 1,1-dimethyl-2-phenylthioethyl, 2-methyl-3-phenylthiopropyl, (2-methoxyphenylthio) methyl, ( 3-methoxyphenylthio) methyl, 2- (4
-Methoxyphenylthio) ethyl, 1- (2-ethoxyphenylthio) ethyl, 3- (4-isopropoxyphenylthio) propyl, 4- (3-pentyloxyphenylthio) butyl, 5- (4-hexyloxyphenyl) Thio) pentyl, 6- (2-butyloxyphenylthio)
Hexyl, (3,4-dimethoxyphenylthio) methyl, (3-ethoxy-4-methoxyphenylthio) methyl, 2- (2,3-dimethoxyphenylthio) ethyl,
1- (2,6-dimethoxyphenylthio) ethyl, 2-
(3,4,5-trimethoxyphenylthio) ethyl group and other alkyl moieties which may have from 1 to 6 straight or branched alkoxy groups having 1 to 6 carbon atoms as substituents on a phenyl ring. A phenylthioalkyl group which is a linear or branched alkyl group having 1 to 6 carbon atoms can be exemplified.

The phenylsulfinyl-substituted lower alkyl group which may have a lower alkoxy group as a substituent on the phenyl ring includes, for example, phenylsulfinylmethyl, 2-phenylsulfinylethyl, 1-phenylsulfinylethyl, 3-phenylsulfinylpropyl 4-phenylsulfinylbutyl, 5-phenylsulfinylpentyl, 6-phenylsulfinylhexyl, 1,1-dimethyl-2-phenylsulfinylethyl, 2-methyl-3-phenylsulfinylpropyl,
(2-methoxyphenylsulfinyl) methyl, (3-
Methoxyphenylsulfinyl) methyl, 2- (4-methoxyphenylsulfinyl) ethyl, 1- (2-ethoxyphenylsulfinyl) ethyl, 3- (4-isopropoxyphenylsulfinyl) propyl, 4- (3-
Pentyloxyphenylsulfinyl) butyl, 5-
(4-hexyloxyphenylsulfinyl) pentyl, 6- (2-butyloxyphenylsulfinyl) hexyl, 3,4-dimethoxyphenylsulfinyl) methyl, 3-ethoxy-4-methoxyphenylsulfinyl) methyl, 2- (2,3 -Dimethoxyphenylsulfinyl) ethyl, 1- (2,6-dimethoxyphenylsulfinyl) ethyl, 2- (3,4,5-trimethoxyphenylsulfinyl) ethyl or the like having 1 to 6 carbon atoms as a substituent on a phenyl ring. And a phenylsulfinylalkyl group which is a linear or branched alkyl group having 1 to 6 carbon atoms in the alkyl moiety which may have 1 to 3 linear or branched alkoxy groups.

The phenylsulfonyl-substituted lower alkyl group which may have a lower alkoxy group as a substituent on the phenyl ring includes, for example, phenylsulfonylmethyl,
2-phenylsulfonylethyl, 1-phenylsulfonylethyl, 3-phenylsulfonylpropyl, 4-phenylsulfonylbutyl, 5-phenylsulfonylpentyl, 6-phenylsulfonylhexyl, 1,1-dimethyl-2-phenylsulfonylethyl, 2- Methyl-3-
Phenylsulfonylpropyl, (2-methoxyphenylsulfonyl) methyl, (3-methoxyphenylsulfonyl) methyl, 2- (4-methoxyphenylsulfonyl)
Ethyl, 1- (2-ethoxyphenylsulfonyl) ethyl, 3- (4-isopropoxyphenylsulfonyl) propyl, 4- (3-pentyloxyphenylsulfonyl) butyl, 5- (4-hexyloxyphenylsulfonyl) pentyl, 6 -(2-butyloxyphenylsulfonyl) hexyl, 3,4-dimethoxyphenylsulfonylmethyl, 3-ethoxy-4-methoxyphenylsulfonyl) methyl, 2- (2,3-dimethoxyphenylsulfonyl) ethyl, 1- (2, A linear or branched alkoxy group having 1 to 6 carbon atoms as a substituent on a phenyl ring such as 6-dimethoxyphenylsulfonyl) ethyl or 2- (3,4,5-trimethoxyphenylsulfonyl) ethyl group; The alkyl moiety which may have up to 3 carbon atoms has 1 carbon atom
And a phenylsulfonylalkyl group which is a straight-chain or branched-chain alkyl group of (1) to (6).

As a 5- to 14-membered monocyclic, dimeric or ternary saturated or unsaturated heterocyclic group having 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur Is, for example, pyrrolidinyl, piperidinyl, piperazinyl, morpholino, pyridyl, thienyl, quinolyl, 1,
4-dihydroquinolyl, benzothiazolyl, pyrazinyl, pyrimidyl, pyridazinyl, pyrrolyl, carbostyril, 3,4-dihydrocarbostyril, 1,2,3
4-tetrahydroquinolyl, indolyl, isoindolyl, indolinyl, benzimidazolyl, benzoxazolyl, imidazolidinyl, isoquinolyl, quinazolidinyl, quinoxalinyl, cinnonyl, phthalazinyl, chromanyl, isoindolinyl, isochromanyl, pyrazolyl, imidazolyl, pyrazolidinyl, 3-azolidinyl , Perhydrobenzofuryl, benzofuryl, benzothienyl, 4H-chromenyl, 1,3,4-
Oxadiazolyl, 1,2,4-triazolyl, 1,
2,3,4-tetrazolyl, 1,3,4-triazolyl, 1,2,4-oxadiazolyl, 2,3-dihydrobenzofuryl, perhydrobenzofuryl, 5-1H-indazolyl, furyl, pyrrolinyl, noryl, oxazolyl , Isoxazolyl, thiazolyl, thiazolidinyl,
1,2,3,5-oxathiadiazolyl, isothiazolyl, pyranyl, pyrazolidinyl, quinuclidinyl, 1,
4-benzoxazinyl, 3,4-dihydro-2H-
1,4-benzoxazinyl, 1,4-benzothiazinyl, 1,2,3,4-tetrahydroquinoxalinyl,
1,3-dithia-2,4-dihydronaphthalenyl, 1,
4-dithianaphthalenyl, furo [3.2-c] pyridyl, furo [2.3-g] quinolyl, 3,4-dihydrofuro [2.3-g] quinolyl, 1,2,3,4-tetrahydro Flow [2.3-g] quinolyl, 1,4-benzodioxanyl, 1,2,4-triazinyl, naphtho [2,1
-B] furyl, imidazo [1, 2-a] pyridyl group and the like.

A 5- to 14-membered monocyclic, dimeric or ternary saturated or unsaturated heterocyclic-substituted lower ring having 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur Examples of the alkyl group include pyrrolidinylmethyl, 2
-Piperidinylethyl, 3-piperazinylpropyl, 4
-Morpholinobutyl, (2-pyridyl) methyl, (3-
Pyridyl) methyl, (2-thienyl) methyl, (3-quinolyl) methyl, 5- (6-quinolyl) pentyl, 6-
(1,4-dihydro-2-quinolyl) hexyl, (2-
Benzothiazolyl) methyl, 2- (3-pyrazinyl) ethyl, 1- (2-pyrimidyl) ethyl, 3- (3-pyridazinyl) propyl, 4- (2-pyrrolyl) butyl,
-(3-carbostyril) pentyl, 6- (3,4-dihydrocarbostyril-6-yl) hexyl, (1,
2,3,4-tetrahydroquinolyl-8-yl) methyl, (2-indolyl) methyl, (3-indolyl) methyl, 2- (3-indolyl) ethyl, (4-isoindolyl) methyl, 2- (3 -Indolinyl) ethyl,
(2-benzimidazolyl) methyl, 3- (5-benzoxazolyl) propyl, 4- (4-imidazolidinyl) butyl, 5- (1-isoquinolyl) pentyl, 6-
(7-quinazolidinyl) hexyl, (8-quinoxalinyl) methyl, 1- (4-cinnolinyl) ethyl, 3-
(5-phthalazinyl) propyl, 4- (6-chromanyl) butyl, 5- (4-isoindolinyl) pentyl,
6- (7-isochromanyl) hexyl, (3-pyrazolyl) methyl, 2- (2-imidazolyl) ethyl, 3-
(3-pyrazolidinyl) propyl, (2-benzofuryl) methyl, (3-benzofuryl) methyl, 4- (6-
Benzofuryl) butyl, (2-benzothienyl) methyl, (3-benzothienyl) methyl, 5- (5-benzothienyl) pentyl, [6- (4H-chromenyl)] methyl, (2,3-dihydro-2- (Benzofuryl) methyl, (2-perhydrobenzofuryl) methyl, (5-1)
H-indazolyl) methyl, thienylmethyl, 1- (5
-Isoindolinyl) ethyl, 3- (2-imidazolinyl) propyl, 4- (2-pyrolinyl) butyl, (2-
(Furyl) methyl, (4-oxazolyl) methyl, (5-
Oxazolyl) methyl, 5- (4-oxazolyl) pentyl, 6- (3-isoxazolyl) hexyl, (4-
(Thiazolyl) methyl, (2-thiazolyl) methyl, 2-
(3-isothiazolyl) ethyl, (2-pyranyl) methyl, 3- (3-pyrazolidinyl) propyl, 4- (2-
Pyrazolinyl) butyl, 5- (2-quinuclidinyl) pentyl, (6-1,4-benzoxazinyl) methyl,
(3,4-dihydro-2H-1,4-benzoxazin-2-yl) methyl, (3,4-dihydro-2H-1,
4-benzoxazin-2-yl) methyl, 1,4-benzothiazin-5-yl) methyl, (1,2,3,4-
Tetrahydroquinoxalinyl-6-yl) methyl,
(1,3-dithia-2,4-dihydronaphthalene-6-
Yl) methyl, (1,4-dithianaphthalen-7-yl) methyl, (5-thiazolyl) methyl, (1,3,4
-Oxadiazolin-5-yl) methyl, (1,2,4
-Triazol-5-yl) methyl, (1,2,3,4
-Tetrazol-5-yl) methyl, (1,3,4-triazol-5-yl) methyl, (1,2,4-oxadiazol-5-yl) methyl, (1,2,4-triazine- (3-yl) methyl, (thiazolidinin-5-yl) methyl, (1,2,3,5-oxathiadiazolin-4-yl) methyl, (3-furyl) methyl, (2-furyl) methyl, ( 2-imidazolyl) methyl, 2- (5
-Thiazolyl) ethyl, 1- (1,3,4-oxadiazolin-2-yl) ethyl, 3- (1,2,4-triazol-3-yl) propyl, 4- (1,2,3, 4-
Tetrazol-5-yl) butyl, 6- (1,3,4-
Triazol-2-yl) hexyl, 2- (1,2,4
-Oxadiazol-3-yl) ethyl, 1- (1,
2,4-triazin-5-yl) ethyl, 3- (thiazolidinin-2-yl) propyl, 4- (1,2,3,5
-Oxathiadiazolin-4-yl) butyl, 5- (furo [3.2-c] pyridin-2-yl) pentyl, 6-
(Furo [2.3-g] quinolin-7-yl) hexyl,
(3,4-dihydrofuro [2.3-g] quinoline-8-
Yl) methyl, 2- (1,2,3,4-tetrahydrofuro [2.3-g] quinolin-4-yl) ethyl, (1,
4-benzodioxan-2-yl) methyl, 1- (1,
4-benzodioxan-3-yl) ethyl, (2,3-
Dihydrobenzofuran-2-yl) methyl, (perhydrobenzofuran-2-yl) methyl, naphtho [2,1-
b] furylmethyl, 4- (naphtho [2,1-b] furyl) pentyl, imidazo [1,2-a] pyridylmethyl, 2- (imidazo [1,2-a] pyridyl) ethyl,
The heterocyclic-substituted alkyl group which is a straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms in the alkyl moiety such as a 1- (imidazo [1,2-a] pyridyl) ethyl group can be exemplified.

The phenoxy-substituted lower alkyl group includes
For example, phenoxymethyl, 2-phenoxyethyl, 1
An alkyl moiety such as phenoxyethyl, 3-phenoxypropyl, 4-phenoxybutyl, 5-phenoxypentyl, 6-phenoxyhexyl, 1,1-dimethyl-2-phenoxyethyl, 2-methyl-3-phenoxypropyl, Phenoxyalkyl groups which are linear or branched alkyl groups of the formulas 1 to 6 can be mentioned.

The phenyl lower alkoxy group which may have an amino group which may have a lower alkanoyl group as a substituent on the phenyl ring includes, for example, benzyloxy, 2-phenylethoxy, 1-phenylethoxy,
3-phenylpropoxy, 4-phenylbutoxy, 5-
Phenylpentyloxy, 6-phenylhexoxyoxy,
1,1-dimethyl-2-phenylethoxy, 2-methyl-3-phenylpropoxy, 4-acetylaminobenzyloxy, 2- (2-propionylaminophenyl) ethoxy, 1- (3-butyrylaminophenyl) ethoxy, 3- (4-pentanoylaminophenyl) propoxy, 4- (3-tert-butylcarbonylaminophenyl) butoxy, 5- (4-hexanoylaminophenyl) pentyloxy, 6- (3,4-bisacetylaminophenyl ) Hexyloxy, 3,4,5-triacetylaminobenzyloxy, 2,4-bisacetylaminobenzyloxy, 4-aminobenzyloxy, 2,3-
Diaminobenzyloxy, 2,4,6-triaminobenzyloxy, 2- (3-aminophenyl) ethoxy, 3
An alkoxy moiety such as-(2-aminophenyl) propoxy is a straight-chain or branched alkoxy group having 1 to 6 carbon atoms, and a straight-chain or branched alkoxy group having 1 to 6 carbon atoms as a substituent on the phenyl ring; Examples include a phenylalkoxy group which may have 1 to 3 amino groups which may have a branched alkanoyl group.

Examples of lower alkoxy-substituted lower alkoxy groups include methoxymethoxy, 3-methoxypropoxy, 4-ethoxybutoxy, 6-propoxyhexyloxy, 5-isopropoxypentyloxy, 1,1-dimethyl-2-butoxyethoxy, 2-methyl-3-te
C1-C6 linear or branched alkoxy group such as rt-butoxypropoxy, 2-pentyloxyethoxy, hexyloxymethoxy group, etc. Substituted C1-C6 linear or branched alkoxy group. be able to.

The lower alkanoyloxy group-substituted lower alkyl group includes, for example, acetyloxymethyl, 2,2-
Dimethylpropionyloxymethyl, propionyloxymethyl, 2-propionyloxyethyl, 1-acetyloxyethyl, 1-butyryloxyethyl, 3-acetyloxypropyl, 4-isobutyryloxybutyl,
5-pentanoyloxypentyl, 6-tert-butylcarbonyloxyhexyl, 1,1-dimethyl-2-
A linear or branched alkanoyloxy group having 2 to 6 carbon atoms, such as a hexanoyloxyethyl or 2-methyl-3-acetyloxypropyl group, or a linear or branched alkyl group having 1 to 6 carbon atoms. Can be mentioned.

Examples of the halogen atom-substituted lower alkyl group include trifluoromethyl, trichloromethyl,
Chloromethyl, bromomethyl, fluoromethyl, iodomethyl, difluoromethyl, dibromomethyl, 2-chloroethyl, 2,2,2-trifluoroethyl, 2,2
2-trichloroethyl, 3-chloropropyl, 2,3-
Dichloropropyl, 4,4,4-trichlorobutyl, 4
-Fluorobutyl, 5-chloropentyl, 3-chloro-
A straight chain having 1 to 6 carbon atoms and having 1 to 3 halogen atoms as a substituent such as 2-methylpropyl, 5-bromohexyl, 5,6-dichlorohexyl, 5-bromohexyl, or 5,6-dichlorohexyl group; Alternatively, a branched alkyl group can be exemplified.

Examples of the tetrazolyl group which may have a lower alkyl group as a substituent on the tetrazole ring include, for example, tetrazolyl, 1-methyltetrazolyl, 2-methyl-tetrazolyl, 5-ethyltetrazolyl, 5-propyl A linear or branched alkyl group having 1 to 6 carbon atoms as a substituent on a tetrazole ring such as tetrazolyl, 1-butyltetrazolyl, 2-pentyltetrazolyl, or 1-hexyltetrazolyl group. Examples thereof include a tetrazolyl group which may be present.

A phenyl group which may have a substituent selected from the group consisting of a lower alkyl group, a lower alkoxy-substituted lower alkoxy group, a hydroxyl group, a halogen atom and a lower alkoxy group on the phenyl ring includes, for example, phenyl, -Methylphenyl, 3-methylphenyl, 4-methylphenyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 3-isopropylphenyl,
4-hexylphenyl, 3,4-dimethylphenyl,
2,5-dimethylphenyl, 3,4,5-trimethylphenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2-ethoxyphenyl, 3
-Ethoxyphenyl, 4-ethoxyphenyl, 4-isopropoxyphenyl, 4-pentyloxyphenyl,
2,4-dimethoxyphenyl, 4-hexyloxyphenyl, 3,4-dimethoxyphenyl, 3-ethoxy-4
-Methoxyphenyl, 2,3-dimethoxyphenyl,
3,4-diethoxyphenyl, 2,5-dimethoxyphenyl, 2,6-dimethoxyphenyl, 3,5-dimethoxyphenyl, 3,4-dipentyloxyphenyl, 3,
4,5-trimethoxyphenyl, 2-chlorophenyl,
3-chlorophenyl, 4-chlorophenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-bromophenyl, 3-bromophenyl, 4-chlorophenyl
Bromophenyl, 2-iodophenyl, 3-iodophenyl, 4-iodophenyl, 3,4-dichlorophenyl, 3,5-dichlorophenyl, 2,6-dichlorophenyl, 2,3-dichlorophenyl, 2,4-dichlorophenyl, 3, 4-difluorophenyl, 3,5-dibromophenyl, 3,4,5-trichlorophenyl, 2-methoxy-5-chlorophenyl, 3-chloro-4-methoxyphenyl, 3-methoxy-5-iodophenyl, 3,
4-dimethoxy-5-bromophenyl, 3,5-diiodo-4-methoxyphenyl, 2-hydroxy-5-chlorophenyl, 2-methoxymethoxy-5-chlorophenyl, 2-hydroxyphenyl, 3-hydroxyphenyl, 4-hydroxy Phenyl, 2,3-dihydroxyphenyl, 3,4-dihydroxyphenyl, 3,4,5-
Trihydroxyphenyl, 2-methoxymethoxyphenyl, 3- (3-methoxypropoxy) phenyl, 4-
(4-ethoxybutoxy) phenyl, 2- (6-propoxyhexyloxy) phenyl, 3- (5-isopropoxypentyloxy) phenyl, 4- (1,1-dimethyl-2-butoxyethoxy) phenyl, 2- ( 2-methyl-3-tert-butoxypropoxy) phenyl, 3
A substituent having a carbon number of 1 to 6 on a phenyl ring such as-(2-pentyloxyethoxy) phenyl, 4-hexyloxymethoxyphenyl, 2,3-dimethoxymethoxyphenyl, or 3,4,5-trimethoxymethoxyphenyl; A straight-chain or branched alkyl group having 1 to 6 carbon atoms, a straight-chain or branched alkoxy group having 1 to 6 carbon atoms, a straight-chain or branched alkoxy group having 1 to 6 carbon atoms, a hydroxyl group, a halogen atom and a carbon number 1
And a phenyl group which may have 1 to 3 groups selected from the group consisting of 1 to 6 linear or branched alkoxy groups.

Examples of the lower alkenyl group include straight-chain or branched-chain alkenyl having 2 to 6 carbon atoms such as vinyl, allyl, 2-butenyl, 3-butenyl, 1-methylallyl, 2-pentenyl and 2-hexenyl. Groups.

Examples of the morpholinocarbonyl lower alkoxy group include morpholinocarbonylmethoxy and 2-
Morpholinocarbonylethoxy, 1-morpholinocarbonylethoxy, 3- (2-morpholinylcarboxy) propoxy, 4- (3-morpholinylcarbonyl) butoxy, 1,1-dimethyl-2- (2-morpholinylcarbonyl) Ethoxy, 5-morpholinocarbonylpentyloxy, 6-morpholinocarbonylhexyloxy, 2-
A morpholinocarbonylalkoxy group in which the alkoxy moiety such as a methyl-3-morpholinocarbonylpropoxy group is a linear or branched alkoxy group having 1 to 6 carbon atoms can be exemplified.

Examples of the morpholinocarboxy lower alkyl group include morpholinocarbonylmethyl, 2-morpholinocarbonylethyl, 1-morpholinocarbonylethyl, 3- (2-morpholinonylcarbonyl) propyl, and 4- (3-morpholinylcarbonyl) Butyl, 1,
Alkyl moieties such as 1-dimethyl-2- (2-morpholinylcarbonyl) ethyl, 5-morpholinocarbonylpentyl, 6-morpholinocarbonylhexyl, and 2-methyl-3-morpholinocarbonylpropyl have 1 to 6 carbon atoms.
And a morpholinocarbonylalkyl group which is a linear or branched alkyl group.

Examples of the cycloalkylcarbonyl group include a cycloalkylcarbonyl group having 3 to 8 carbon atoms such as cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl, cyclohexylcarbonyl, cycloheptylcarbonyl, cyclooctylcarbonyl and the like.

Examples of the phenyl lower alkenylcarbonyl group include cinnamoyl, 4-phenyl-3-butenoyl, 4-phenyl-2-butenoyl, 5-phenyl-4-pentenoyl, 5-phenyl-3-pentenoyl and 5-phenyl -2-pentenoyl, 6-phenyl-
5-hexenoyl, 6-phenyl-4-hexenoyl,
6-phenyl-3-hexenoyl, 6-phenyl-2-
An alkenylcarbonyl group such as hexenoyl, 2-methyl-4-phenyl-3-butenoyl, 2-methyl-cinnamoyl and 1-methyl-cinnamoyl is a linear or branched alkenylcarbonyl group having 3 to 6 carbon atoms. A certain phenylalkenylcarbonyl group can be exemplified.

R ⁶ and R ⁷ , R ⁹ and R ¹⁰ , R ⁴⁰ and R
Examples of the 5- or 6-membered saturated heterocyclic group formed by bonding to each other via a nitrogen atom or an oxygen atom together with or without a nitrogen atom to which ⁴¹ or R ⁵² and R ⁵³ are bonded include pyrrolidinyl, piperidinyl, piperazinyl, Examples include a morpholino group.

The heterocyclic group having 1 to 3 groups selected from the group consisting of a hydroxyl group, a lower alkyl group and a phenyl lower alkyl group includes, for example, 3-hydroxypyrrolidinyl, 2-hydroxypyrrolidinyl, -Hydroxypiperidinyl, 3-hydroxypiperidinyl, 2-hydroxypiperidinyl, 3-hydroxypiperazinyl, 2-hydroxypiperazinyl, 3-hydroxymorpholino,
-Hydroxymorpholino, 4-benzylpiperazinyl,
3- (2-phenylethyl) pyrrolidinyl, 2- (3-
Phenylpropyl) pyrrolidinyl, 4- (4-phenylbutyl) piperidinyl, 3- (5-phenylpentyl)
Morpholino, 2- (6-phenylhexyl) piperazinyl, 4-methylpiperazinyl, 3,4-dimethylpiperazinyl, 3-ethylpyrrolidinyl, 2-propylpyrrolidinyl, 3,4,5-trimethylpi Peridinyl, 4-butylpiperidinyl, 3-pentylmorpholino, 2-hexylpiperazinyl, 3-methyl-4-benzylpiperazinyl, 3-ethyl-4-hydroxypiperidinyl, 3-
A hydroxyl group such as a methyl-4-benzylpyrrolidinyl group, a linear or branched alkyl group having 1 to 6 carbon atoms and a linear or branched alkyl group having 1 to 6 carbon atoms in the alkyl group portion; Groups selected from the group consisting of certain phenylalkyl groups
The above-mentioned heterocyclic groups having two or more groups can be exemplified.

Examples of the amino group which may have a group selected from the group consisting of a lower alkanoyl group and a phenyl-lower alkenylcarbonyl group include, for example, amino, formylamino, acetylamino, propionylamino, butyrylamino and isobutyi. Rylamino, pentanoylamino, t-butylcarbonylamino, hexanoylamino, cinnamoylamino, 4-phenyl-3-butenoylamino, 4-phenyl-2-butenoylamino, 5-phenyl-4-pentenoylamino, 5-phenyl -3-pentenoylamino, 5-phenyl-2-pentenoylamino, 6-phenyl-5-hexenoylamino, 6-phenyl-4-hexenoylamino, 6-phenyl-3-hexenoylamino, 6-phenyl-2-
Hexenoylamino, 2-methyl-4-phenyl-3-
Butenoylamino, 2-methyl-cinnamoylamino,
1-methyl-cinnamoylamino, N-acetyl-N-
A linear or branched alkanoyl group having 1 to 6 carbon atoms as a substituent such as a cinnamoylamino group and phenylalkenyl wherein the alkenylcarbonyl moiety is a linear or branched alkenylcarbonyl group having 3 to 6 carbon atoms Examples include an amino group which may have 1 to 2 groups selected from the group consisting of a carbonyl group.

Examples of the amino group which may have a lower alkanoyl group as a substituent include, for example, amino, formylamino, acetylamino, propionylamino, butyrylamino, isobutyrylamino, pentanoylamino, tert-butylcarbonylamino, hexa Examples of the substituent such as a noylamino group include an amino group having a linear or branched alkanoyl group having 1 to 6 carbon atoms.

The lower alkylsulfinyl group includes, for example, methylsulfinyl, ethylsulfinyl, isopropylsulfinyl, butylsulfinyl, tert-
Examples thereof include a linear or branched alkylsulfinyl group having 1 to 6 carbon atoms such as butylsulfinyl, pentylsulfinyl, and hexylsulfinyl.

Examples of the lower alkylthio group include straight-chain or branched-chain alkylthio groups having 1 to 6 carbon atoms such as methylthio, ethylthio, propylthio, isopropylthio, butylthio, tert-butylthio, pentylthio, and hexylthio. .

Examples of the lower alkylsulfonyl group include straight-chain or branched-chain alkyl groups having 1 to 6 carbon atoms such as methylsulfonyl, ethylsulfonyl, isopropylsulfonyl, butylsulfonyl, tert-butylsulfonyl, pentylsulfonyl and hexylsulfonyl. An example is a sulfonyl group.

Examples of the lower alkanoyloxy group include those having 1 to 6 carbon atoms such as formyloxy, acetyloxy, propionyloxy, butyryloxy, isobutyryloxy, pentanoyloxy, tert-butylcarbonyloxy, and hexanoyloxy groups. A linear or branched alkanoyloxy group can be exemplified.

The amino-substituted lower alkyl group which may have a group selected from the group consisting of lower alkylsulfonyl group and lower alkanoyl group includes, for example, aminomethyl, 2-aminoethyl, 1-aminoethyl, 3-aminopropyl, 4-aminobutyl, 5-aminopentyl, 6-aminohexyl, 1,1-dimethyl-
2-aminoethyl, 2-methyl-3-aminopropyl,
Formylaminomethyl, 1-acetylaminoethyl, 2
-Propionylaminoethyl, 3-butyrylaminopropyl, 4-pentanoylaminopentyl, 5-hexanoylaminohexyl, 6-isobutyrylaminohexyl, 1,1-dimethyl-2-acetylaminoethyl, 2
-Methyl-3-formylaminopropyl, methylsulfonylaminomethyl, 2-ethylsulfonylaminoethyl, 1-isopropylsulfonylaminoethyl, 3-butylsulfonylaminopropyl, 4-tert-butylsulfonylaminobutyl, 5-pentylsulfonylaminopentyl , 6-hexylsulfonylaminohexyl,
As a substituent such as a 1,1-dimethyl-2-methylsulfonylaminoethyl, 2-methyl-3-ethylsulfonylaminopropyl, N-methylsulfonylamino-N-acetylaminomethyl group, a straight chain having 1 to 6 carbon atoms or A group selected from the group consisting of a branched alkylsulfonyl group and a linear or branched alkanoyl group having 1 to 6 carbon atoms,
Examples thereof include a linear or branched alkyl group having 1 to 6 carbon atoms having an amino group which may be present.

The 1,3-dioxofuranyl-substituted lower alkyl group which may have a lower alkyl group as a substituent includes, for example, (1,3-dioxolan-2-yl)
Methyl, 2- (1,3-dioxolan-4-yl) ethyl, 1- (1,3-dioxolan-2-yl) ethyl,
3- (1,3-dioxolan-4-yl) propyl, 4
-(1,3-dioxolan-2-yl) butyl, 2-
(1,3-dioxolan-2-yl) propyl, 5-
(1,3-dioxolan-2-yl) pentyl, (4-
Hexyl-1,3-dioxolan-2-yl) methyl,
(2,4-dimethyl-1,3-dioxolan-2-yl) methyl, 6- (1,3-dioxolan-3-yl)
Hexyl, 4- (2-propyl-1,3-dioxolan-2-yl) butyl, 5- (4-butyl-1,3-dioxolan-2-yl) pentyl, 6- (2-pentyl-
1,3-dioxolan-2-yl) hexyl, 1,1-
Dimethyl-2- (1,3-dioxolan-2-yl) ethyl, 2-methyl-3- (1,3-dioxolan-2-
Yl) propyl, (2-methyl-1,3-dioxolan-2-yl) methyl, 2- (4-ethyl-1,3-dioxolanyl-2-yl) ethyl, 3- (2,4,5-trimethyl An alkyl moiety such as -1,3-dioxolan-2-yl) propyl group is a straight-chain or branched alkyl group having 1 to 6 carbon atoms, and a straight-chain or branched chain having 1 to 6 carbon atoms as a substituent. 1, which may have 1 to 3 chain alkyl groups.
An example is a 3-dioxolanyl-substituted alkyl group.

The lower alkanoyl group-substituted lower alkyl group includes, for example, formylmethyl, acetylmethyl,
-Propionylethyl, 1-butyrylethyl, 3-isobutyrylpropyl, 4-pentanoylbutyl, 5-hexanoylhexyl, 6-tert-butylcarbonylhexyl, 1,1-dimethyl-2-acetylethyl, 2-
An alkanoyl moiety such as a methyl-3-acetylmethyl group is a linear or branched alkanoyl group having 1 to 6 carbon atoms, and an alkyl moiety is a linear or branched alkyl group having 1 to 6 carbon atoms. Certain alkanoylalkyl groups can be exemplified.

The aminocarbonyl-substituted lower alkyl group which may have a lower alkyl group as a substituent includes:
For example, aminocarbonylmethyl, 2-aminocarbonylethyl, 1-aminocarbonylethyl, 3-aminocarbonylpropyl, 4-aminocarbonylbutyl,
Aminocarbonylpentyl, 6-aminocarbonylhexyl, 1,1-dimethyl-2-aminocarbonylethyl, 2-methyl-3-aminocarbonylpropyl, methylaminocarbonylmethyl, 1-ethylaminocarbonylethyl, 2-propylaminocarbonylethyl , 3-
Isopropylaminocarbonylpropyl, 4-butylaminocarbonylbutyl, 5-pentylaminocarbonylpentyl, 6-hexylaminocarbonylhexyl, dimethylaminocarbonylmethyl, 2-diethylaminocarbonylethyl, 2-dimethylaminocarbonylethyl, (N-ethyl-N -Propylamino) carbonylmethyl, 2- (N-methyl-N-hexylamino) carbonylethyl group, etc. having 1 to 2 straight or branched alkyl groups having 1 to 6 carbon atoms as substituents. A straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms having a certain aminocarbonyl group can be exemplified.

The lower alkenyl group substituted by lower alkoxycarbonyl group includes, for example, 2-methoxycarbonylvinyl, 2-ethoxycarbonylvinyl, 3-propoxycarbonylallyl, 4-butoxycarbonyl-2-butenyl, 4-pentyloxycarbonyl-3 -Butenyl,
3-hexyloxycarbonyl-1-methylallyl, 5
-Isopropoxycarbonyl-2-pentenyl, 6-t
an alkenyl moiety such as ert-butoxycarbonyl-2-hexenyl group is a linear or branched alkenyl group having 2 to 6 carbon atoms, wherein the alkenyl group is substituted with a linear or branched alkoxycarbonyl group having 1 to 6 carbon atoms; Can be exemplified.

The aminocarbonyl group which may have a lower alkyl group as a substituent includes, for example, 2-aminocarbonylvinyl, 3-aminocarbonylallyl, 4-aminocarbonyl-2-butenyl, 4-amino Carbonyl-3-butenyl, 3-aminocarbonyl-1-methylallyl, 5-aminocarbonyl-2-pentenyl, 6-aminocarbonyl-2-hexenyl, 2-methylaminocarbonylvinyl, 3-ethylaminocarbonylallyl, 4-propyl Aminocarbonyl-2-butenyl, 4-isopropylaminocarbonyl-3-butenyl, 3-butylaminocarbonyl-1-methylallyl, 5-pentylaminocarbonyl-2-pentenyl, 6-hexylaminocarbonyl-2-hexenyl, 2-dimethyl Iminocarbonyl vinyl, 2-diethylamino-carbonyl-vinyl, 3- (N-ethyl--N- propylamino carbonyl) allyl, 4-(N-methyl -
(N-hexylaminocarbonyl) -2-butenyl group or the like having 2 or more carbon atoms substituted by an aminocarbonyl group which may have 1 to 2 linear or branched alkyl groups having 1 to 6 carbon atoms as a substituent. And 6 straight-chain or branched alkenyl groups.

Examples of the carboxy-substituted lower alkenyl group include 2-carboxyvinyl, 3-carboxyallyl, 4-carboxy-2-butenyl, 4-carboxy-3-butenyl, 3-carboxy-1-methylallyl,
5-carboxy-2-pentenyl, 6-carboxy-2
-Having 2 to 2 carbon atoms substituted by a carboxy group such as a hexenyl group;
And 6 straight-chain or branched alkenyl groups.

Examples of the aminocarbonyl group which may have a lower alkyl group as a substituent include, for example, aminocarbonyl, methylaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl, isopropylaminocarbonyl, butylaminocarbonyl, tert-butylaminocarbonyl , Pentylaminocarbonyl, hexylaminocarbonyl, dimethylaminocarbonyl,
Diethylaminocarbonyl, dipropylaminocarbonyl, dibutylaminocarbonyl, dipentylaminocarbonyl, dihexylaminocarbonyl, N-methyl-N
Straight-chain or straight-chain having 1 to 6 carbon atoms as a substituent such as -ethylaminocarbonyl, N-ethyl-N-propylaminocarbonyl, N-methyl-N-butylaminocarbonyl, N-methyl-N-hexylaminocarbonyl; An aminocarbonyl group which may have 1 to 2 branched alkyl groups can be exemplified.

The phenylsulfonyl group which may have a lower alkyl group as a substituent on the phenyl ring includes:
For example, phenylsulfonyl, 2-methylphenylsulfonyl, 3-methylphenylsulfonyl, 4-methylphenylsulfonyl, 2-ethylphenylsulfonyl, 3
-Ethylphenylsulfonyl, 4-ethylphenylsulfonyl, 3-isopropylphenylsulfonyl, 4-hexylphenylsulfonyl, 3,4-dimethylphenylsulfonyl, 2,5-dimethylphenylsulfonyl,
A phenylsulfonyl group which may have 1 to 3 straight or branched alkyl groups having 1 to 6 carbon atoms as a substituent on a phenyl ring such as a 3,4,5-trimethylphenylsulfonyl group can be exemplified.

Examples of the phenyl lower alkenyl group include styryl, cinnamyl, 4-phenyl-3-butenyl, 4-phenyl-2-butenyl and 5-phenyl-4-
Pentenyl, 5-phenyl-3-pentenyl, 5-phenyl-2-pentenyl, 6-phenyl-5-hexenyl, 6-phenyl-4-hexenyl, 6-phenyl-3
An alkenyl moiety such as -hexenyl, 6-phenyl-2-hexenyl, 2-methyl-4-phenyl-3-butenyl, 2-methyl-cinnamyl, 1-methyl-cinnamyl group or the like having 2 to 6 carbon atoms. A phenylalkenyl group which is a branched alkenyl group can be exemplified.

A benzoyl group which may have, on the phenyl ring, a lower alkoxy group as a substituent, a halogen atom, an amino group which may have a lower alkanoyl as a substituent and a hydroxyl group which may have 1 to 3 groups. Is, for example, benzoyl, 2-chlorobenzoyl, 3-
Chlorobenzoyl, 4-chlorobenzoyl, 2-fluorobenzoyl, 3-fluorobenzoyl, 4-fluorobenzoyl, 2-bromobenzoyl, 3-bromobenzoyl, 4-bromobenzoyl, 2-iodobenzoyl,
4-iodobenzoyl, 3,5-dichlorobenzoyl,
2,6-dichlorobenzoyl, 3,4-dichlorobenzoyl, 3,4-difluorobenzoyl, 3,5-dibromobenzoyl, 3,4,5-trichlorobenzoyl,
-Methoxybenzoyl, 3-methoxybenzoyl, 4-
Methoxybenzoyl, 2-ethoxybenzoyl, 3-ethoxybenzoyl, 4-ethoxybenzoyl, 4-isopropoxybenzoyl, 4-hexyloxybenzoyl, 3,4-dimethoxybenzoyl, 3,4-diethoxybenzoyl, 3,4,5 -Trimethoxybenzoyl,
2,5-dimethoxybenzoyl, 3-methoxy-4-chlorobenzoyl, 2-chloro-6-methoxybenzoyl, 2-methoxy-5-chlorobenzoyl, 2-aminobenzoyl, 3-aminobenzoyl, 4-aminobenzoyl, -Hydroxybenzoyl, 3-hydroxybenzoyl, 4-hydroxybenzoyl, 2,5-diaminobenzoyl, 3,4,5-triaminobenzoyl, 2-
Formylaminobenzoyl, 3-acetylaminobenzoyl, 4-acetylaminobenzoyl, 2-acetylaminobenzoyl, 3-propionylaminobenzoyl,
4-butyrylaminobenzoyl, 2-isobutyrylaminobenzoyl, 3-pentanoylaminobenzoyl, 3
-Tert-butylcarbonylaminobenzoyl, 4-
Hexanoylaminobenzoyl, 2,6-diacetylaminobenzoyl, 2,4-dihydroxybenzoyl,
A linear or branched alkoxy group having 1 to 6 carbon atoms, a halogen atom, a substituent as a substituent on a phenyl ring such as a 2,4,6-trihydroxybenzoyl group or a 2-hydroxy-5-chlorobenzoyl group; And a benzoyl group which may have 1 to 3 groups selected from the group consisting of an amino group and a hydroxyl group which may have a linear or branched alkanoyl group having 1 to 6 carbon atoms.

An amino-substituted lower alkanoyl group which may have a lower alkanoyl group as a substituent includes:
For example, 2-aminoacetyl, 3-aminopropionyl, 2-aminopropionyl, 4-aminobutyryl,
-Aminopentanoyl, 6-aminohexanoyl, 2,
2-dimethyl-3-aminopropionyl, 2-methyl-
3-aminopropionyl, 2-acetylaminoacetyl, 2-acetylaminopropionyl, 3-propionylaminopropionyl, 3-isopropionylaminopropionyl, 4-butyrylaminobutyryl, 5-pentanoylaminopentanoyl, 6-hexanoyl C2 having an amino group which may have 1 to 2 straight or branched alkanoyl groups having 1 to 6 carbon atoms as a substituent such as aminohexanoyl or 2-formylaminoacetyl group;
To 6 linear or branched alkanoyl groups.

Examples of the amino-substituted sulfonyl group which may have a lower alkyl group as a substituent include, for example, aminosulfonyl, methylaminosulfonyl, ethylaminosulfonyl, propylaminosulfonyl, isopropylaminosulfonyl, butylaminosulfonyl, tert
-Butylaminosulfonyl, pentylaminosulfonyl, hexylaminosulfonyl, dimethylaminosulfonyl, diethylaminosulfonyl, dipropylaminosulfonyl, dibutylaminosulfonyl, dipentylaminosulfonyl, dihexylaminosulfonyl, N-methyl-N-ethylaminosulfonyl, N-ethyl A linear or branched alkyl group having 1 to 6 carbon atoms as a substituent such as -N-propylaminosulfonyl, N-methyl-N-butylaminosulfonyl, N-methyl-N-hexylaminosulfonyl or the like; An aminosulfonyl group which may have two may be exemplified.

The lower alkylenedioxy group includes, for example, a methylenedioxy, ethylenedioxy, trimethylenedioxy, tetramethylenedioxy group, etc.
And 4 linear or branched alkylenedioxy groups.

The phenyl group which may have a lower alkoxy group as a substituent on the phenyl ring includes, for example,
Phenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2-ethoxyphenyl, 3
-Ethoxyphenyl, 4-ethoxyphenyl, 4-isopropoxyphenyl, 4-pentyloxyphenyl,
2,4-dimethoxyphenyl, 4-hexyloxyphenyl, 3,4-dimethoxyphenyl, 3-ethoxy-4
-Methoxyphenyl, 2,3-dimethoxyphenyl,
3,4-diethoxyphenyl, 2,5-dimethoxyphenyl, 2,6-dimethoxyphenyl, 3,5-dimethoxyphenyl, 3,4-dipentyloxyphenyl, 3,
A phenyl group which may have 1 to 3 straight or branched chain alkoxy groups having 1 to 6 carbon atoms as a substituent on a phenyl ring such as a 4,5-trimethoxyphenyl group can be exemplified.

The 2,3-dihydro-1H-indenyl ring may have, on the 2,3-dihydro-1H-indenyl ring, a group selected from the group consisting of an oxo group, a hydroxyl group, and a silyloxy group having a lower alkyl group as a substituent. Examples of the dihydro-1H-indenyl group-substituted lower alkyl group include, for example, (2,
3-dihydro-1H-inden-2-yl) methyl, 2
-(2,3-dihydro-1H-inden-1-yl) ethyl, 1- (2,3-dihydro-1H-indene-3-
Yl) ethyl, 3- (2,3-dihydro-1H-inden-4-yl) propyl, 4- (2,3-dihydro-1
H-inden-5-yl) butyl, 5- (2,3-dihydro-1H-inden-6-yl) pentyl, 6-
(2,3-dihydro-1H-inden-7-yl) hexyl, (1-oxo-2,3-dihydro-1H-inden-2-yl) methyl, (1-hydroxy-2,3-dihydro-1H) -Inden-2-yl) methyl, (1-dimethyl, tert-butylsilyloxy-2,3-dihydro-1H-inden-2-yl) methyl, (1,3-
Dihydroxy-2,3-dihydro-1H-indene-2
-Yl) methyl, [1,3-bis (trimethylsilyloxy) -2,3-dihydro-1H-inden-2-yl) methyl, (1,3,7-trihydroxy-2,3-
Dihydro-1H-inden-2-yl) methyl, [1,
3,4-tri (dimethyl, ethylsilyloxy) -2,
On a 2,3-dihydro-1H-indenyl ring such as a 3-dihydro-1H-inden-2-yl) methyl group, an oxo group as a substituent, a hydroxyl group, and a straight or branched chain having 1 to 6 carbon atoms as a substituent. A linear or branched C1-C6 substituted by a 2,3-dihydro-1H-indenyl group which may have 1 to 3 groups selected from the group consisting of silyloxy groups having 3 chain alkyl groups; A chain alkyl group can be exemplified.

Examples of the silyloxy group having a lower alkyl group as a substituent include, for example, trimethylsilyloxy, triethylsilyloxy, triisopropylsilyloxy, tributylsilyloxy, tri-tert-butylsilyloxy, tripentylsilyloxy, trihexylsilyl. Examples thereof include a silyloxy group in which three straight or branched alkyl groups having 1 to 6 carbon atoms such as oxy, dimethyl, and tert-butylsilyloxy groups are substituted.

Examples of the phenyl group which may have a substituent selected from the group consisting of a lower alkoxy group and a halogen atom on the phenyl ring include phenyl, 2-phenyl and the like.
Methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2-ethoxyphenyl, 3-ethoxyphenyl, 4-ethoxyphenyl, 4-isopropoxyphenyl, 4-pentyloxyphenyl, 2,4-dimethoxyphenyl, 4-hexyl Oxyphenyl, 3,4-dimethoxyphenyl, 3-ethoxy-4-methoxyphenyl, 2,3-dimethoxyphenyl, 3,4-diethoxyphenyl, 2,5-dimethoxyphenyl, 2,6-dimethoxyphenyl, 3, 5-dimethoxyphenyl, 3,4
-Dipentyloxyphenyl, 3,4,5-trimethoxyphenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-fluorophenyl, 3-
Fluorophenyl, 4-fluorophenyl, 2-bromophenyl, 3-bromophenyl, 4-bromophenyl,
2-iodophenyl, 3-iodophenyl, 4-iodophenyl, 3,4-dichlorophenyl, 3,5-dichlorophenyl, 2,6-dichlorophenyl, 2,3-dichlorophenyl, 2,4-dichlorophenyl, 3,4-difluoro Phenyl, 3,5-dibromophenyl, 3,
4,5-trichlorophenyl, 2-methoxy-5-chlorophenyl, 3-chloro-4-methoxyphenyl, 3-
Methoxy-5-iodophenyl, 3,4-dimethoxy-
As a substituent on a phenyl ring such as 5-bromophenyl and 3,5-diiodo-4-methoxyphenyl, a group having 1 to 1 carbon atoms.
And a phenyl group which may have 1 to 3 groups selected from the group consisting of 6 straight or branched alkoxy groups and halogen atoms.

Examples of the 5- or 6-membered saturated or unsaturated heterocyclic group having 1-4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur are, for example, pyrrolidinyl, piperidinyl, piperazinyl, morpholino , Pyridyl, thienyl, pyrazinyl, pyrimidyl, pyridazinyl, pyrrolyl, imidazodinyl, pyrazolyl, imidazolyl, pyrazolidinyl, 1,3,4-oxadiazolyl, 1,2,4-triazolyl, 1,2,3,4-tetrazolyl, 1,3 , 4-Triazolyl, 1,2,4-oxadiazolyl, furyl, pyrrolinyl, oxazolyl,
Isoxazolyl, thiazolyl, thiazolidinyl, 1,
2,3,5-oxathiadiazolyl, isothiazolyl,
Examples thereof include a pyranyl, pyrazolidinyl, 1,2,4-triazinyl group and the like.

Examples of the 5- or 6-membered saturated or unsaturated heterocyclic-substituted lower alkyl group having 1-4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur are, for example, pyrrolidinylmethyl, 2-piperidinylethyl, 3-
Piperazinylpropyl, 4-morpholinobutyl, (2-
Pyridyl) methyl, (3-pyridyl) methyl, (2-thienyl) methyl, 2- (3-pyrazinyl) ethyl, 1-
(2-pyrimidyl) ethyl, 3- (3-pyridazinyl)
Propyl, 4- (2-pyrrolyl) butyl, 4- (4-imidazolidinyl) butyl, (2-imidazolyl) methyl, (3-pyrazolyl) methyl, 2- (2-imidazolyl) ethyl, 3- (3-pyrazolidinyl) Propyl, thienylmethyl, 3- (2-imidazolinyl) propyl,
4- (2-pyrolinyl) butyl, (2-furyl) methyl, (4-oxazolyl) methyl, (5-oxazolyl) methyl, 5- (4-oxazolyl) pentyl, 6-
(3-isoxazolyl) hexyl, (4-thiazolyl) methyl, (2-thiazolyl) methyl, 2- (3-isothiazolyl) ethyl, (2-pyranyl) methyl, 3-
(3-pyrazolidinyl) propyl, 4- (2-pyrazolinyl) butyl, (5-thiazolyl) methyl, (1,3
4-oxadiazolin-5-yl) methyl, (1,2,2
4-triazol-5-yl) methyl, (1,2,3,
4-tetrazol-5-yl) methyl, (1,3,4-
(Triazol-5-yl) methyl, (1,2,4-oxadiazol-5-yl) methyl, (1,2,4-triazin-3-yl) methyl, (thiazolidin-5-yl) methyl, ( 1,2,3,5-oxathiadiazolin-4-yl) methyl, (2-furyl) methyl, (3-furyl) methyl, 2- (5-thiazolyl) ethyl, 1-
(1,3,4-oxadiazolin-2-yl) ethyl,
3- (1,2,4-triazol-3-yl) propyl, 4- (1,2,3,4-tetrazol-5-yl)
Butyl, 6- (1,3,4-triazol-2-yl)
Hexyl, 2- (1,2,4-oxadiazole-3-
Yl) ethyl, 1- (1,2,4-triazin-5-yl) ethyl, 3- (thiazolidine-2-yl) propyl, 4- (1,2,3,5-oxathiadiazoline-4)
-Yl) The heterocyclic-substituted alkyl group in which the alkyl moiety such as a butyl group is a linear or branched alkyl group having 1 to 6 carbon atoms can be exemplified.

A 5- to 14-membered monocyclic, dimeric or ternary saturated or unsaturated heterocyclic-substituted lower ring having 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur Examples of the alkenyl group include 2-benzofurylvinyl, 3-benzofuryl-2-propenyl, 4-benzofuryl-3-butenyl, 3-benzofuryl-2-butenyl, 2-methyl-3-benzofuryl-2-propenyl,
5-benzofuryl-4-pentenyl, 5-benzofuryl-2-pentenyl, 4-benzofuryl-3-pentenyl, 6-benzofuryl-5-hexenyl, 6-benzofuryl-4-hexenyl, 6-benzofuryl-3-hexenyl, 6- Benzofuryl-2-hexenyl, β-methyl-4-benzofuryl-3-butenyl, 5-benzofuryl-2,4-pentadienyl, 4-benzofuryl-1,3
-Butadienyl, 6-benzofuryl-2,4-hexadienyl, 6-benzofuryl-3,5-hexadienyl,
6-benzofuryl-1,3-hexadienyl, 5-benzofuryl-1,3-pentadienyl, 2-benzothienylvinyl, 3-benzothienyl-2-propenyl, 4-
Benzothienyl-3-butenyl, 3-benzothienyl-
2-butenyl, 2-methyl-3-benzothienyl-2-
Propenyl, 5-benzothienyl-4-pentenyl, 5
-Benzothienyl-2-pentenyl, 6-benzothienyl-5-hexenyl, 6-benzothienyl-4-hexenyl, 6-benzothienyl-3-hexenyl, 6-benzothienyl-2-hexenyl, β-methyl-4- Benzothienyl-3-butenyl, 5-benzothienyl-2,4
-Bentadienyl, 4-benzothienyl-1,3-butadienyl, 6-benzothienyl-2,4-hexadienyl, 6-benzothienyl-3,5-hexadienyl, 6
-Benzothienyl-1,3-hexadienyl, 5-benzothienyl-1,3-pentadienyl, 2- (furo [3.2-c] pyridyl) vinyl, 3- (furo [3.2
-C] pyridyl) -2-propenyl, 4- (furo [3.
2-c] pyridyl) -3-butenyl, 3- (furo [3.
2-c] pyridyl) -2-butenyl, 2-methyl-3-
(Flo [3.2-c] pyridyl) -2-propenyl, 5
-(Furo [3.2-c] pyridyl) -4-pentenyl,
5- (furo [3,2-c] pyridyl) -2-pentenyl, 6- (furo [3.2-c] pyridyl) -5-hexenyl, 6- (furo [3.2-c] pyridyl)- 4-hexenyl, 6- (furo [3.2-c] pyridyl) -3-hexenyl, 6- (furo [3.2-c] pyridyl) -2-
Hexenyl, β-methyl-4- (furo [3.2-c] pyridyl) -3-butenyl, 5- (furo [3.2-c] pyridyl) -2,4-pentadienyl, 4- (furo [3 .
2-c] pyridyl) -1,3-butadienyl, 6- (furo [3.2-c] pyridyl) -2,4-hexadienyl, 6- (furo [3.2-c] pyridyl) -3,5 -Hexadienyl, 6- (furo [3.2-c] pyridyl)-
1,3-hexadienyl, 5- (furo [3.2-c] pyridyl) -1,3-pentadienyl, 2-quinolylvinyl, 3- (1,4-dihydroquinolyl) -2-propenyl, 4-benzothiazolyl- 3-butenyl, 3-carbostyryl-2-butenyl, 2-methyl-3- (3,4-
Dihydrocarbostyril) -2-propenyl, 5-
(1,2,3,4-tetrahydroquinolyl) -4-pentenyl, 5-indolyl-2-pentenyl, 6-isoindolyl-5-hexenyl, 6-indolinyl-4-hexenyl, 6-benzimidazolyl-3-hexenyl,
6-benzoxazolyl-2-hexenyl, β-methyl-4-isoquinolyl-3-butenyl, 5-quinazolidinyl-2,4-pentadienyl, 4-cinnolyl-1,3
-Butadienyl, 6-quinoxalinyl-2,4-hexadienyl, 6-phthalazinyl-3,5-hexadienyl, 6-chromanyl-1,3-hexadienyl, 5-isoindolinyl-1,3-pentadienyl, 2- (4H
-Chromenyl) vinyl, 3- (2,3-dihydro-2-
Benzofuryl) -2-propenyl, 4- (2-perhydrobenzofuryl) -3-butenyl, 3- (1,4-benzoxazinyl) -2-butenyl, 2-methyl-3-
(3,4-dihydro-2H-1,4-benzoxazinyl) -2-propenyl, 5- (1,4-benzothiazinyl) -4-pentenyl, 5- (1,2,3,4-tetrahydro Quinoxalinyl) -2-pentenyl, 6- (1,
3-dithia-2,4-dihydronaphthalenyl) -5-hexenyl, 6- (1,4-dithianaphthalenyl) -4-
Hexenyl, 6- (1,4-benzodioxanyl) -3
-Hexenyl, 2-pyrrolidinylvinyl, 3-pyrrolidinyl-2-propenyl, 4-pyrrolidinyl-3-butenyl, 3-pyrrolidinyl-2-butenyl, 2-methyl-3
-Pyrrolidinyl-2-propenyl, 5-pyrrolidinyl-
4-pentenyl, 5-pyrrolidinyl-2-pentenyl,
4-pyrrolidinyl-3-pentenyl, 6-pyrrolidinyl-5-hexenyl, 6-pyrrolidinyl-4-hexenyl, 6-pyrrolidinyl-3-hexenyl, 6-pyrrolidinyl-2-hexenyl, β-methyl-4-pyrrolidinyl-3- Butenyl, 5-pyrrolidinyl-2,4-pentadienyl, 4-pyrrolidinyl-1,3-butadienyl, 6
-Pyrrolidinyl-2,4-hexadienyl, 6-pyrrolidinyl-3,5-hexadienyl, 6-pyrrolidinyl-
1,3-hexadienyl, 5-pyrrolidinyl-1,3-
Pentadienyl, 2-piperidinylvinyl, 3-piperidinyl-2-propenyl, 4-piperidinyl-3-butenyl, 3-piperidinyl-2-butenyl, 2-methyl-
3-piperidinyl-2-propenyl, 5-piperidinyl-4-pentenyl, 5-piperidinyl-2-pentenyl, 6-piperidinyl-5-hexenyl, 6-piperidinyl-4-hexenyl, 6-piperidinyl-3-hexenyl, 6- Piperidinyl-2-hexenyl, β-methyl-4-piperidinyl-3-butenyl, 5-piperidinyl-2,4-bentadenyl, 4-piperidinyl-1,3
-Butadienyl, 6-piperidinyl-2,4-hexadienyl, 6-piperidinyl-3,5-hexadienyl,
6-piperidinyl-1,3-hexadienyl, 5-piperidinyl-1,3-pentadienyl, 2-piperazinylvinyl, 3-piperazinyl-2-propenyl, 4-piperazinyl-3-butenyl, 3-piperazinyl-2-butenyl , 2-methyl-3-piperazinyl-2-propenyl, 5-piperazinyl-4-pentenyl, 5-piperazinyl-2-pentenyl, 6-piperazinyl-5-hexenyl, 6-piperazinyl-4-hexenyl, 6-piperazinyl-3 -Hexenyl, 6-piperazinyl-2-hexenyl, β-methyl-4-piperazinyl-3-butenyl, 5-piperazinyl-2,4-pentadienyl, 4-
Piperazinyl-1,3-butadienyl, 6-piperazinyl-2,4-hexadienyl, 6-piperazinyl-3,
5-hexadienyl, 6-piperazinyl-1,3-hexadienyl, 5-piperazinyl-1,3-pentadienyl, 2-morpholinovinyl, 3-pyridyl-2-propenyl, 4-thienyl-3-butenyl, 3-pyrazinyl-
2-butenyl, 2-methyl-3-pyrimidyl-2-propenyl, 2-pyridazinylvinyl, 3-pyrrolyl-2-
Propenyl, 4-imidazolyl-3-butenyl, 3-imidazolyl-2-butenyl, 2-methyl-3-imidazolyl-2-propenyl, 5-imidazolyl-4-pentenyl, 5-imidazolyl-2-pentenyl, 4-imidazolyl- 3-pentenyl, 6-imidazolyl-5-hexenyl, 6-imidazolyl-4-hexenyl, 6-imidazolyl-3-hexenyl, 6-imidazolyl-2-hexenyl, β-methyl-4-imidazolyl-3-butenyl, 5- Imidazolyl-2,4-pentadienyl, 4-
Imidazolyl-1,3-butadienyl, 6-imidazolyl-2,4-hexadienyl, 6-imidazolyl-3,
5-hexadienyl, 6-imidazolyl-1,3-hexadienyl, 5-imidazolyl-1,3-pentadienyl, 2-imidazolidinylvinyl, 3-pyrazolyl-2
-Propenyl, 4-pyrazolidinyl-3-butenyl, 3
-Perhydrobenzofuryl-2-butenyl, 2-methyl-3- (1,3,4-oxadiazolyl) -2-propenyl, 5- (1,2,4-triazolyl) -4-pentenyl, 5- (1 , 2,3,4-tetrazolyl) -2-pentenyl, 6- (1,3,4-triazolyl) -5-hexenyl, 6- (1,2,4-oxadiazolyl) -4
-Hexenyl, 6- (2,3-dihydro-2-benzofuryl) -3-hexenyl, 6-pyrrolinyl-2-hexenyl, β-methyl-4-nonyl-3-butenyl, 5-isoxazolyl-2,4-ventadenyl , 4-thiazolyl-1,3-butadienyl, 6-thiazolidinyl-
2,4-hexadienyl, 6- (1,2,3,5-oxathiadiazolyl) -3,5-hexadienyl, 6-isothiazolyl-1,3-hexadienyl, 5-pyranyl-1,3-pentadienyl, 2 -Oxazolyl vinyl,
3-oxazolyl-2-propenyl, 4-oxazolyl-3-butenyl, 3-oxazolyl-2-butenyl, 2
-Methyl-3-oxazolyl-2-propenyl, 5-oxazolyl-4-pentenyl, 5-oxazolyl-2-
Pentenyl, 4-oxazolyl-3-pentenyl, 6-
Oxazolyl-5-hexenyl, 6-oxazolyl-4
-Hexenyl, 6-oxazolyl-3-hexenyl, 6
-Oxazolyl-2-hexenyl, β-methyl-4-oxazolyl-3-butenyl, 5-oxazolyl-2,4
-Pentadienyl, 4-oxazolyl-1,3-butadienyl, 6-oxazolyl-2,4-hexadienyl,
6-oxazolyl-3,5-hexadienyl, 6-oxazolyl-1,3-hexadienyl, 5-oxazolyl-1,3-pentadienyl, 2-pyrazolylvinyl, 3
-Quinuclidinyl-2-propenyl, 4-benzothiazolyl-3-butenyl, 3-carbostyryl-2-butenyl, 2-methyl-3- (3,4-dihydro [2,3-
g] quinolyl) -2-propenyl, 5- (1,2,3,
4-tetrahydrofuro [2,3-g] quinolyl) -4-
Pentenyl, 2- (naphtho [2,1-b] furyl) vinyl, 3- (naphtho [2,1-b] furyl) -2-propenyl, 4- (naphtho [2,1-b] furyl) -3 -Butenyl, 3- (naphtho [2,1-b] furyl) -2-butenyl, 2-methyl-3- (naphtho [2,1-b] furyl) -2-propenyl, 5- (naphtho [2, 1-b] furyl) -4-pentenyl, 5- (naphtho [2,1-b]
Furyl) -2-pentenyl, 4- (naphtho [2,1-
b] Furyl) -3-pentenyl, 6- (naphtho [2,1
-B] furyl) -5-hexenyl, 6- (naphtho [2,
1-b] furyl) -4-hexenyl, 6- (naphtho [2,1-b] furyl) -3-hexenyl, 6- (naphtho [2,1-b] furyl) -2-hexenyl, β-methyl -4- (naphtho [2,1-b] furyl) -3-butenyl, 5- (naphtho [2,1-b] furyl) -2,4-pentadienyl, 4- (naphtho [2,1-b] Frill)-
1,3-butadienyl, 6- (naphtho [2,1-b] furyl) -2,4-hexadienyl, 6- (naphtho [2,
1-b] furyl) -3,5-hexadienyl, 6- (naphtho [2,1-b] furyl) -1,3-hexadienyl, 5- (naphtho [2,1-b] furyl) -1,3 -Pentadienyl, 2- (imidazo [1,2-a] pyridyl) vinyl, 3- (imidazo [1,2-a] pyridyl)
Alkenyl moieties such as -2-propenyl and 4- (imidazo [1,2-a] pyridyl) -3-butenyl group have 2 carbon atoms;
And the above-mentioned heterocyclic-substituted alkenyl group which is an alkenyl group having 1 to 2 linear or branched double bonds.

Examples of the phenyl lower alkoxycarbonyl group include benzyloxycarbonyl, 2-phenylethoxycarbonyl, 1-phenylethoxycarbonyl, 3-phenylpropoxycarbonyl, 4-phenylbutoxycarbonyl, 5-phenylpentyloxycarbonyl, Phenylhexyloxycarbonyl, 1,
1-dimethyl-2-phenylethoxycarbonyl, 2-
Examples thereof include a phenylalkoxycarbonyl group in which an alkoxycarbonyl moiety such as a methyl-3-phenylpropoxycarbonyl group is a linear or branched alkoxycarbonyl group having 1 to 6 carbon atoms.

The lower alkoxycarbonyloxy-substituted lower alkyl group includes, for example, methoxycarbonyloxymethyl, ethoxycarbonyloxymethyl, 2-ethoxycarbonyloxyethyl, 1-ethoxycarbonyloxyethyl, 3-methoxycarbonyloxypropyl, 4-ethoxy Carbonyloxybutyl, 6-propoxycarbonyloxyhexyl, 5-isopropoxycarbonyloxypentyl, 1,1-dimethyl-2-butoxycarbonyloxyethyl, 2-methyl-3-ter
An alkyl moiety such as a t-butoxycarbonyloxypropyl, 2-pentyloxycarbonyloxyethyl, hexyloxycarbonyloxymethyl group or the like is a straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms. A chain or branched alkoxycarbonyloxyalkyl group can be exemplified.

Examples of the benzoyl-substituted lower alkyl group which may have a halogen atom as a substituent on the phenyl ring include, for example, benzoylmethyl, 1- (2-chlorobenzoyl) ethyl, 2- (3-chlorobenzoyl) ethyl, -(4-chlorobenzoyl) propyl, 4-
(2-fluorobenzoyl) butyl, 1,1-dimethyl-2- (3-fluorobenzoyl) ethyl, 5- (4-
Fluorobenzoyl) pentyl, 6- (2-bromobenzoyl) hexyl, 2-methyl-3- (3-bromobenzoyl) propyl, (4-bromobenzoyl) methyl,
2- (2-iodobenzoyl) ethyl, 1- (4-iodobenzoyl) ethyl, (3,5-dichlorobenzoyl) methyl, 2- (2,6-dichlorobenzoyl) ethyl, 1- (3,4-dichloro Benzoyl) ethyl, 3-
(3,4-difluorobenzoyl) propyl, (3,5
-Dibromobenzoyl) methyl, (3,4,5-trichlorobenzoyl) methyl and the like may have 1 to 3 halogen atoms as substituents on the phenyl ring, and the alkyl portion is a straight-chain having 1 to 6 carbon atoms. A phenylalkyl group which is a chain or branched alkyl group can be exemplified.

Examples of the amino group which may have a lower alkanoyl group as a substituent include, for example, amino, formylamino, acetylamino, propionylamino, butyrylamino, isobutyrylamino, pentanoylamino, tert-butylcarbonylamino, hexa Examples of a substituent such as a noylamino group include an amino group having a linear or branched alkanoyl group having 1 to 6 carbon atoms.

The compounds of the present invention include the following compounds.

(1) R ¹ represents a hydrogen atom, R ² ,
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ³ , R ⁴ , m, n and r are the same as described above.

(2) R ¹ represents a halogen atom, R ² ,
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ³ , R ⁴ , m, n and r are the same as described above.

(3) R ¹ represents a lower alkyl group,
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ² , R ³ , R ⁴ , m, n and r are the same as described above.

[0116] (4) R ² is a hydrogen atom, R ^1,
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ³ , R ⁴ , m, n and r are the same as described above.

(5) R ² represents a lower alkyl group which may have a halogen atom as a substituent, and R ¹ , R ³ ,
R ⁴ , m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(6) R ² represents a phenyl group, and R ¹ and R
³ , a quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ⁴ , m, n and r are the same as described above.

(7) R ² represents a morpholino-substituted lower alkyl group, and R ¹ , R ³ , R ⁴ , m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof. .

(8) R ² represents an imidazolyl-substituted lower alkyl group, and R ¹ , R ³ , R ⁴ , m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof .

(9) R ³ is a hydrogen atom, R ⁴ is a group represented by the above-mentioned [Formula 27], and R ¹ , R ² , m, n and r
Is a quinoxaline derivative represented by the above general formula (1) or a salt thereof.

(10) R ³ is a lower alkyl group, R ⁴ is a group represented by the above formula [Chem. 27], and R ¹ , R ² , m, n and r are the same as those in the above-mentioned general formula (1) Or a salt thereof.

(11) R ³ represents a hydrogen atom, and R ⁴ represents a group selected from the group consisting of a lower alkoxy group as a substituent, a halogen atom, a lower alkanoyl group and a phenyl lower alkenylcarbonyl group as a substituent on a phenyl ring. An amino group which may have a lower alkoxy group, a lower alkoxy group substituted with a lower alkoxy group, a tetrazolyl group which may have a lower alkyl group as a substituent on the tetrazole ring, a hydroxyl group, a group -O
—A ₄ —CO—NR ⁴⁰ R ⁴¹ (A ₄ , R ⁴⁰ and R ⁴¹ are as defined above), a lower alkenyloxy group, a nitro group and a lower alkyl group which may have a halogen atom as a substituent. A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ¹ , R ² , m, n and r represent a phenyl lower alkenyl group which may have a substituted group.

[0124] (12) R ³ is a lower alkyl group, R ⁴
Is a lower alkoxy group as a substituent on the phenyl ring, a halogen atom, an amino group which may have a group selected from the group consisting of a lower alkanoyl group and a phenyl lower alkenylcarbonyl group as a substituent, a lower alkoxy group-substituted lower alkoxy group, A tetrazolyl group, which may have a lower alkyl group as a substituent on the tetrazole ring, a hydroxyl group,
Group _{-O-A 4 -CO-N-} R 40 R 41 (A 4, R 40 and R
⁴¹ is the same as described above), a phenyl lower alkenyl group which may have a group selected from the group consisting of a lower alkenyloxy group, a nitro group and a lower alkyl group which may have a halogen atom as a substituent, and R ¹ , A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ² , m, n and r are the same as described above.

(13) R ³ represents a hydrogen atom, R ⁴ represents a lower alkenyl group, and R ¹ , R ² , m, n and r are the same as defined above, and are quinoxaline derivatives represented by the general formula (1) Or a salt thereof.

[0126] (14) R ³ is a lower alkyl group, R ⁴
Represents a lower alkenyl group, and R ¹ , R ² , m, n and r
Is a quinoxaline derivative represented by the above general formula (1) or a salt thereof.

(15) R^ThreeRepresents a hydrogen atom;^FourBut shiku
R represents a lower alkyl group; ¹, R^Two, M, n
And r represent the same quino represented by the general formula (1)
Xaline derivatives or salts thereof.

[0128] (16) R ³ is a lower alkyl group, R ⁴
Represents a cycloalkyl lower alkyl group, and R ¹ , R ² ,
m, n and r are the same as described above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(17) R ³ represents a hydrogen atom, R ⁴ represents a naphthyl lower alkyl group, R ¹ , R ² , m, n and r
Is a quinoxaline derivative represented by the above general formula (1) or a salt thereof.

[0130] (18) R ³ is a lower alkyl group, R ⁴
Represents a naphthyl lower alkyl group; R ¹ , R ² , m, n
And r are the same as described above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

[0131] (19) R ³ is a hydrogen atom, a phenylthio substituted lower alkyl group wherein R ⁴ which may have a lower alkoxy group as a substituent on the phenyl ring, R ^1,
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ² , m, n and r are the same as described above.

[0132] (20) R ³ is a lower alkyl group, R ⁴
Represents a phenylthio-substituted lower alkyl group which may have a lower alkoxy group as a substituent on the phenyl ring,
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ¹ , R ² , m, n and r are the same as described above.

(21) R ³ represents a hydrogen atom; R ⁴ represents a phenylsulfinyl-substituted lower alkyl group which may have a lower alkoxy group as a substituent on a phenyl ring; R ¹ , R ² , m, n And r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

[0134] (22) R ³ is a lower alkyl group, R ⁴
Represents a phenylsulfinyl-substituted lower alkyl group which may have a lower alkoxy group as a substituent on the phenyl ring, and R ¹ , R ² , m, n and r are represented by the same general formula (1) as described above. Quinoxaline derivatives or salts thereof.

(23) R ³ represents a hydrogen atom, and R ⁴ represents a phenylsulfonyl-substituted lower alkyl group which may have a lower alkoxy group as a substituent on a phenyl ring;
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ¹ , R ² , m, n and r are the same as described above.

[0136] (24) R ³ is a lower alkyl group, R ⁴
Represents a phenylsulfonyl-substituted lower alkyl group which may have a lower alkoxy group as a substituent on the phenyl ring, and R ¹ , R ² , m, n and r are represented by the same general formula (1) as described above. Quinoxaline derivatives or salts thereof.

(25) R ³ represents a hydrogen atom, R ⁴ represents a phenoxy-substituted lower alkyl group, R ¹ , R ² , m, n
And r are the same as described above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

[0138] (26) R ³ is a lower alkyl group, R ⁴
Represents a phenoxy-substituted lower alkyl group, and R ¹ , R ² ,
m, n and r are the same as described above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(27) R ³ represents a hydrogen atom, R ⁴ represents a group represented by the above formula, and R ¹ , R ² , m, n and r have the same general formula (1) And a salt thereof.

[0140] (28) R ³ is a lower alkyl group, R ⁴
Represents a group represented by the above-mentioned [Chemical Formula 28], and R ¹ , R ² ,
m, n and r are the same as described above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(29) R ³ represents a hydrogen atom, and R ⁴ represents a group
A ₅ -CR ⁴² R ⁴³ R ⁴⁴ (A ₅ , R ⁴² , R ⁴³ and R ⁴⁴ are the same as described above), and R ¹ , R ² , m, n and r are the same as those of the general formula (1) And a salt thereof.

[0142] (30) R ³ is a lower alkyl group, R ⁴
Is a group -A ₅ -CR ⁴² R ⁴³ R ⁴⁴ (A ₅ , R ⁴² , R ⁴³ and R
⁴⁴ is the same as defined above), and R ¹ , R ² , m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(31) R ³ represents a hydrogen atom, and R ⁴ represents 2,
2,3-dihydro-1H-indenyl group which may have on the 3-dihydro-1H-indenyl ring a group selected from the group consisting of an oxo group, a hydroxyl group and a silyloxy group having a lower alkyl group as a substituent. A quinoxaline derivative represented by the general formula (1) or a salt thereof, which represents a substituted lower alkyl group, wherein R ¹ , R ² , m, n and r are the same as described above.

[0144] (32) R ³ is a lower alkyl group, R ⁴
May have a group selected from the group consisting of an oxo group, a hydroxyl group and a silyloxy group having a lower alkyl group as a substituent on the 2,3-dihydro-1H-indenyl ring. A quinoxaline derivative represented by the general formula (1) or a salt thereof, which represents an indenyl group-substituted lower alkyl group, wherein R ¹ , R ² , m, n and r are the same as described above.

(33) R ³ represents a hydrogen atom, R ⁴ represents a group represented by the above formula, and R ¹ , R ² , m, n and r have the same general formula (1) And a salt thereof.

[0146] (34) R ³ is a lower alkyl group, R ⁴
Represents a group represented by the above-mentioned [Formula 34], and R ¹ , R ² ,
m, n and r are the same as described above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(35) R ³ and R ⁴ represent a 1,2,3,4-tetrahydroisoquinolyl group formed by bonding together with the nitrogen atom to which they are bonded (having a lower alkoxy group on the group) A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ¹ , R ² , m, n and r are the same as described above.

(36) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (4), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as defined in (9) or (10).

(37) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (4), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as defined in the above (11) or (12).

(38) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (4), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as in the above (13) or (14).

(39) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (4), and R ³ and R ⁴ represent the above
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as in the above (15) or (16).

(40) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (4), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as in the above (17) or (18).

(41) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (4), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as in the above (17) or (18).

(42) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (4), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as defined in (19) or (20).

(43) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (4), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as defined in (21) or (22).

(44) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (4), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as defined in (23) or (24).

(45) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (4), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as defined in the above (25) or (26).

(46) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (4), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as defined in (27) or (28).

(47) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (4), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as defined in (29) or (30).

(48) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (4), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as defined in the above (31) or (32).

(49) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (4), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as defined in the above (33) or (34).

(50) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (4), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1), wherein m, n and r are the same as defined above, wherein m, n and r are the same as defined above, or a salt thereof.

(51) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (5), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as defined in (9) or (10).

(52) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (5), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as defined in the above (11) or (12).

(53) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (5), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as in the above (13) or (14).

(54) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (5), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as in the above (15) or (16).

(55) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (5), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as in the above (17) or (18).

(56) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (5), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as defined in (19) or (20).

(57) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (5), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as defined in (21) or (22).

(58) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (5), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as defined in (23) or (24).

(59) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (5), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as defined in the above (25) or (26).

(60) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (5), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as defined in (27) or (28).

(61) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (5), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as defined in (29) or (30).

(62) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (5), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as defined in the above (31) or (32).

(63) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (5), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as defined in the above (33) or (34).

(64) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (5), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1), wherein m, n and r are the same as defined above, wherein m, n and r are the same as defined above, or a salt thereof.

(65) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (6), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as defined in (9) or (10).

(66) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (6), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as defined in the above (11) or (12).

(67) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (6), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as in the above (13) or (14).

(68) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (6), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as in the above (15) or (16).

(69) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (6), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as in the above (17) or (18).

(70) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (6), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as defined in (19) or (20).

(71) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (6), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as defined in (21) or (22).

(72) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (6), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as defined in (23) or (24).

(73) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (6), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as defined in the above (25) or (26).

(74) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (6), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as defined in (27) or (28).

(75) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (6), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as defined in (29) or (30).

(76) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (6), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as defined in the above (31) or (32).

(77) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (6), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as defined in the above (33) or (34).

(78) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (6), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1), wherein m, n and r are the same as defined above, wherein m, n and r are the same as defined above, or a salt thereof.

(79) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (7), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as defined in (9) or (10).

(80) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (7), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as defined in the above (11) or (12).

(81) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (7), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as in the above (13) or (14).

(82) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (7), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as in the above (15) or (16).

(83) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (7), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as in the above (17) or (18).

(84) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (7), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as defined in (19) or (20).

(85) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (7), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as defined in (21) or (22).

(86) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (7), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as defined in (23) or (24).

(87) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (7), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as defined in the above (25) or (26).

(88) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (7), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as defined in (27) or (28).

(89) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (7), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as defined in (29) or (30).

(90) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (7), and R ³ and R ⁴ represent the above.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as defined in the above (31) or (32).

(91) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (7), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as defined in the above (33) or (34).

(92) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (7), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1), wherein m, n and r are the same as defined above, wherein m, n and r are the same as defined above, or a salt thereof.

(93) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (8), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as defined in (9) or (10).

(94) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (8), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as defined in the above (11) or (12).

(95) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (8), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as in the above (13) or (14).

(96) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (8), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as in the above (15) or (16).

(97) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (8), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as in the above (17) or (18).

(98) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (8), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as defined in (19) or (20).

(99) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (8), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as defined in (21) or (22).

(100) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (8), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as defined in (23) or (24).

(101) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (8), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as defined in the above (25) or (26).

(102) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (8), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as defined in (27) or (28).

(103) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (8), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as defined in (29) or (30).

(104) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (8), and R ³ and R ⁴ represent the above.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as defined in the above (31) or (32).

(105) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (8), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r have the same definitions as defined in the above (33) or (34).

(106) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (8), and R ³ and R ⁴ represent the above definitions.
A quinoxaline derivative represented by the general formula (1), wherein m, n and r are the same as defined above, wherein m, n and r are the same as defined above, or a salt thereof.

(107) R ¹ is the same as defined in the above (1), and R ³
And R ⁴ have the same definition as in the above (9), and R ² , m, n and r
Is a quinoxaline derivative represented by the above general formula (1) or a salt thereof.

(108) R ¹ is the same as defined in the above (1), and R ³
And R ⁴ are as defined in the above (10), and R ² , m, n and r
Is a quinoxaline derivative represented by the above general formula (1) or a salt thereof.

(109) R ¹ is the same as defined in the above (1), and R ³
And R ⁴ have the same meaning as defined in the above (11), and R ² , m, n and r
Is a quinoxaline derivative represented by the above general formula (1) or a salt thereof.

(110) R ¹ represents the definition of the above (1), and R ³
And R ⁴ are as defined in the above (12), and R ² , m, n and r
Is a quinoxaline derivative represented by the above general formula (1) or a salt thereof.

(111) R ¹ represents the definition of the above (1), and R ³
And R ⁴ have the same meaning as defined in the above (13), and R ² , m, n and r
Is a quinoxaline derivative represented by the above general formula (1) or a salt thereof.

(112) R ¹ is the same as defined in the above (1), and R ³
And R ⁴ have the same definition as in the above (14), and R ² , m, n and r
Is a quinoxaline derivative represented by the above general formula (1) or a salt thereof.

(113) R ¹ is the same as defined in the above (1), and R ³
And R ⁴ have the same definition as in the above (15), and R ² , m, n and r
Is a quinoxaline derivative represented by the above general formula (1) or a salt thereof.

(114) R ¹ is the same as defined in the above (1), and R ³
And R ⁴ are as defined in the above (16), and R ² , m, n and r
Is a quinoxaline derivative represented by the above general formula (1) or a salt thereof.

(115) R ¹ is the same as defined in the above (1), and R ³
And R ⁴ have the same definition as in the above (17), and R ² , m, n and r
Is a quinoxaline derivative represented by the above general formula (1) or a salt thereof.

(116) R ¹ is the same as defined in the above (1), and R ³
And R ⁴ are as defined in the above (18), and R ² , m, n and r
Is a quinoxaline derivative represented by the above general formula (1) or a salt thereof.

(117) R ¹ is the same as defined in the above (1), and R ³
And R ⁴ are as defined in the above (19), and R ² , m, n and r
Is a quinoxaline derivative represented by the above general formula (1) or a salt thereof.

(118) R ¹ is the same as defined in the above (1), and R ³
And R ⁴ have the same definition as in the above (20), and R ² , m, n and r
Is a quinoxaline derivative represented by the above general formula (1) or a salt thereof.

(119) R ¹ is the same as defined in the above (1), and R ³
And R ⁴ have the same definition as in the above (21), and R ² , m, n and r
Is a quinoxaline derivative represented by the above general formula (1) or a salt thereof.

(120) R ¹ represents the definition of the above (1), and R ³
And R ⁴ have the same definition as in the above (22), and R ² , m, n and r
Is a quinoxaline derivative represented by the above general formula (1) or a salt thereof.

(121) R ¹ is the same as defined in the above (1), and R ³
And R ⁴ are as defined in the above (23), and R ² , m, n and r
Is a quinoxaline derivative represented by the above general formula (1) or a salt thereof.

(122) R ¹ is the same as defined in the above (1), and R ³
And R ⁴ have the same definition as in the above (24), and R ² , m, n and r
Is a quinoxaline derivative represented by the above general formula (1) or a salt thereof.

(123) R ¹ is the same as defined in the above (1), and R ³
And R ⁴ have the same definition as in the above (25), and R ² , m, n and r
Is a quinoxaline derivative represented by the above general formula (1) or a salt thereof.

(124) R ¹ is the same as defined in the above (1), and R ³
And R ⁴ have the same meaning as defined in the above (26), and R ² , m, n and r
Is a quinoxaline derivative represented by the above general formula (1) or a salt thereof.

(125) R ¹ is the same as defined in the above (1), and R ³
And R ⁴ have the same definition as in the above (27), and R ² , m, n and r
Is a quinoxaline derivative represented by the above general formula (1) or a salt thereof.

(126) R ¹ is the same as defined in the above (1), and R ³
And R ⁴ have the same definition as in the above (28), and R ² , m, n and r
Is a quinoxaline derivative represented by the above general formula (1) or a salt thereof.

(127) R ¹ is the same as defined in the above (1), and R ³
And R ⁴ are as defined in the above (29), and R ² , m, n and r
Is a quinoxaline derivative represented by the above general formula (1) or a salt thereof.

(128) R ¹ is the same as defined in the above (1), and R ³
And R ⁴ have the same definition as in the above (30), and R ² , m, n and r
Is a quinoxaline derivative represented by the above general formula (1) or a salt thereof.

(129) R ¹ is the same as defined in the above (1), and R ³
And R ⁴ have the same definition as in the above (31), and R ² , m, n and r
Is a quinoxaline derivative represented by the above general formula (1) or a salt thereof.

(130) R ¹ is the same as defined in the above (1), and R ³
And R ⁴ have the same meaning as defined in the above (32), and R ² , m, n and r
Is a quinoxaline derivative represented by the above general formula (1) or a salt thereof.

(131) R ¹ is the same as defined in the above (1), and R ³
And R ⁴ are as defined in the above (33), and R ² , m, n and r
Is a quinoxaline derivative represented by the above general formula (1) or a salt thereof.

(132) R ¹ is the same as defined in the above (1), and R ³
And R ⁴ have the same meaning as defined in the above (34), and R ² , m, n and r
Is a quinoxaline derivative represented by the above general formula (1) or a salt thereof.

(133) R ¹ is the same as defined in the above (1), and R ³
And R ⁴ are as defined in the above (35), and R ² , m, n and r
Is a quinoxaline derivative represented by the above general formula (1) or a salt thereof.

(134) R ¹ represents a lower alkoxy group;
² , a quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ³ , R ⁴ , m, n and r are the same as described above.

(135) R ¹ represents an amino group which may have a lower alkyl group as a substituent, and R ² , R ³ ,
R ⁴ , m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

[0248] (136) R ¹ represents an aminocarbonyl group having optionally a lower alkyl substituent, R ^2,
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ³ , R ⁴ , m, n and r are the same as described above.

(137) R ³ is a phenyl-lower alkoxycarbonyl group, R ⁴ is a group represented by the above-mentioned [Chemical Formula 27], and R ¹ , R ² , m, n and r are the same as those defined above. The quinoxaline derivative represented by (1) or a salt thereof.

(138) A compound wherein R ³ is a lower alkanoyloxy-substituted lower alkyl group and R ⁴ is a group represented by the above formula, and R ¹ , R ² , m, n and r are the same as defined above. A quinoxaline derivative represented by the formula (1) or a salt thereof.

(139) R ³ represents a phenyl lower alkoxycarbonyl group, R ⁴ is selected from the group consisting of a lower alkoxy group as a substituent, a halogen atom, a lower alkanoyl group and a phenyl lower alkenylcarbonyl group as substituents on the phenyl ring. amino group which may have a group, a lower alkoxy-substituted lower alkoxy group, a tetrazolyl group which may have a lower alkyl group as a substituent on the tetrazole ring, a hydroxyl group, a group -O-a ₄ -CO-NR ⁴⁰ R ⁴¹
(A ₄ , R ⁴⁰ and R ⁴¹ are the same as described above), lower alkenyloxy group, nitro group and phenyl lower group which may have a group selected from the group consisting of a lower alkyl group which may have a halogen atom as a substituent. An alkenyl group;
¹ , a quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ² , m, n and r are the same as described above.

(140) R ³ represents a lower alkanoyloxy-substituted lower alkyl group; R ⁴ represents a lower alkoxy group, a halogen atom, a lower alkanoyl group or a phenyl lower alkenylcarbonyl group as a substituent on a phenyl ring; amino group which may have a more selected group, a lower alkoxy-substituted lower alkoxy group, a tetrazolyl group which may have a lower alkyl group as a substituent on the tetrazole ring, a hydroxyl group, a group -O-a ₄ -CO- N
-R ⁴⁰ R ⁴¹ (A ₄ , R ⁴⁰ and R ⁴¹ are as defined above), a lower alkenyloxy group, a nitro group and a group selected from the group consisting of a lower alkyl group which may have a halogen atom as a substituent. A quinoxaline derivative represented by the general formula (1) or a salt thereof, which represents a phenyl lower alkenyl group, and wherein R ¹ , R ² , m, n and r are the same as described above.

(141) R ³ represents a phenyl lower alkoxycarbonyl group, R ⁴ represents a lower alkenyl group,
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ¹ , R ² , m, n and r are the same as described above.

(142) R ³ represents a lower alkanoyloxy-substituted lower alkyl group, R ⁴ represents a lower alkenyl group, and R ¹ , R ² , m, n and r are the same as defined in the above general formula (1) Or a salt thereof.

(143) R ³ represents a phenyl lower alkoxycarbonyl group, R ⁴ represents a cycloalkyl lower alkyl group, and R ¹ , R ² , m, n and r have the same general formula (1) Or a salt thereof.

(144) R ³ represents a lower alkanoyloxy-substituted lower alkyl group, R ⁴ represents a cycloalkyl lower alkyl group, and R ¹ , R ² , m, n and r have the same general formula (I) A quinoxaline derivative or a salt thereof represented by 1).

(145) R ³ represents a phenyl lower alkoxycarbonyl group, R ⁴ represents a naphthyl lower alkyl group, and R ¹ , R ² , m, n and r are the same as those in the above-mentioned general formula (1). Or a salt thereof.

(146) R ³ represents a lower alkanoyloxy-substituted lower alkyl group, R ⁴ represents a naphthyl lower alkyl group, and R ¹ , R ² , m, n and r have the same general formula (1) And a salt thereof.

(147) R ³ represents a phenyl lower alkoxycarbonyl group; R ⁴ represents a phenylthio-substituted lower alkyl group which may have a lower alkoxy group as a substituent on the phenyl ring; R ¹ , R ² , m , N and r are the same as described above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(148) R ³ represents a lower alkanoyloxy-substituted lower alkyl group; R ⁴ represents a phenylthio-substituted lower alkyl group which may have a lower alkoxy group as a substituent on a phenyl ring; R ¹ and R ² , M, n and r
Is a quinoxaline derivative represented by the above general formula (1) or a salt thereof.

(149) R ³ represents a phenyl lower alkoxycarbonyl group, R ⁴ represents a phenylsulfinyl-substituted lower alkyl group which may have a lower alkoxy group as a substituent on the phenyl ring, and R ¹ , R ² , m, n and r are the same as described above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

[0262] (0.99) R ³ represents a lower alkanoyloxy-substituted lower alkyl group, a phenylsulfinyl-substituted lower alkyl group which may R ⁴ has a lower alkoxy group as a substituent on the phenyl ring, R ^1, R ² , m,
n and r are the same as described above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(151) R ³ represents a phenyl lower alkoxycarbonyl group, R ⁴ represents a phenylsulfonyl-substituted lower alkyl group which may have a lower alkoxy group as a substituent on the phenyl ring, and R ¹ , R ² , m, n and r
Is a quinoxaline derivative represented by the above general formula (1) or a salt thereof.

[0264] (152) R ³ represents a lower alkanoyloxy-substituted lower alkyl group, a phenylsulfonyl-substituted lower alkyl group wherein R ⁴ which may have a lower alkoxy group as a substituent on the phenyl ring, R ^1, R ² , m, n
And r are the same as described above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(153) R ³ represents a phenyl lower alkoxycarbonyl group, R ⁴ represents a phenoxy-substituted lower alkyl group, and R ¹ , R ² , m, n and r are the same as those of the above-mentioned general formula (1) Or a salt thereof.

(154) R ³ represents a lower alkanoyloxy-substituted lower alkyl group, R ⁴ represents a phenoxy-substituted lower alkyl group, and R ¹ , R ² , m, n and r have the same general formula (I) A quinoxaline derivative or a salt thereof represented by 1).

(155) R ³ represents a phenyl lower alkoxycarbonyl group, R ⁴ represents a group represented by the above formula, and R ¹ , R ² , m, n and r are the same as defined above. A quinoxaline derivative represented by the formula (1) or a salt thereof.

(156) R ³ represents a lower alkanoyloxy-substituted lower alkyl group, R ⁴ represents a group represented by the above formula, and R ¹ , R ² , m, n and r are as defined above. A quinoxaline derivative represented by a general formula (1) or a salt thereof.

(157) R ³ represents a phenyl lower alkoxycarbonyl group, and R ⁴ represents a group —A ₅ —CR ⁴² R ⁴³ R ⁴⁴ (R
⁴² , R ⁴³ and R ⁴⁴ are the same as defined above), and R ¹ , R ² ,
m, n and r are the same as described above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(158) R ³ represents a lower alkanoyloxy-substituted lower alkyl group, and R ⁴ represents a group —A ₅ —CR ⁴² R ⁴³ R
⁴⁴ (R ⁴² , R ⁴³ and R ⁴⁴ are as defined above), and R ¹ ,
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ² , m, n and r are the same as described above.

(159) R ³ represents a phenyl lower alkoxycarbonyl group, R ⁴ represents a silyloxy group having an oxo group as a substituent, a hydroxyl group and a lower alkyl group as a substituent on a 2,3-dihydro-1H-indenyl ring. 2,3-dihydro-1 which may have a group selected from the group consisting of
H- indenyl group substituted lower alkyl group, R ^1, R
^2. A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as described above.

(160) R ³ represents a lower alkanoyloxy-substituted lower alkyl group, and R ⁴ represents 2,3-dihydro-1H
An oxo group as a substituent on the indenyl ring, a hydroxyl group and a 2,3-dihydro-1H-indenyl group-substituted lower alkyl group which may have a group selected from a silyloxy group having a lower alkyl group as a substituent. And R
¹ , a quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ² , m, n and r are the same as described above.

(161) R ³ represents a phenyl lower alkoxycarbonyl group, R ⁴ represents a group represented by the above formula, and R ¹ , R ² , m, n and r are the same as defined above. A quinoxaline derivative represented by the formula (1) or a salt thereof.

(162) R ³ represents a lower alkanoyloxy-substituted lower alkyl group, R ⁴ represents a group represented by the above formula, and R ¹ , R ² , m, n and r are as defined above. A quinoxaline derivative represented by a general formula (1) or a salt thereof.

[0275] (163) R ³ is a lower alkanoyl group, R ⁴
Represents a group represented by the above-mentioned [Chemical Formula 27], and R ¹ , R ² ,
m, n and r are the same as described above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

[0276] (164) in R ³ is a lower alkoxycarbonyl group represents a group R ⁴ is represented by the chemical formula 27], R ^1, R
^2. A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as described above.

(165) R ³ represents a lower alkanoyl group,
R ⁴ is a lower alkoxy group as a substituent on the phenyl ring,
A halogen atom, an amino group which may have a group selected from the group consisting of a lower alkanoyl group and a phenyl lower alkenylcarbonyl group as a substituent, a lower alkoxy group, a substituted lower alkoxy group, and a lower alkyl group as a substituent on the tetrazole ring tetrazolyl group which may, hydroxyl, group ^{_{-O-a 4 -CO-NR 40}} R 41 (a 4, R 40 and R ⁴¹ are the same as defined above), a lower alkenyloxy group, a halogen atom as a nitro group and a substituted group A phenyl lower alkenyl group which may have a group selected from the group consisting of lower alkyl groups which may have R ¹ , R ² , m, n
And r are the same as described above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(166) R^ThreeIs a lower alkoxycarbonyl group
And R^FourIs a lower alcohol as a substituent on the phenyl ring
Xyl group, halogen atom, lower alkanoyl as a substituent
Group and phenyl-lower-alkenylcarbonyl group
Amino group which may have selected group, lower alkoxy
Si-substituted lower alkoxy group, substituent on tetrazole ring
Which may have a lower alkyl group as a substituent
Group, hydroxyl group, group -OA _Four-CO-NR⁴⁰R
⁴¹(A_Four, R⁴⁰And R⁴¹Is as defined above), lower alkenyl
A halogen atom as a oxy group, a nitro group or a substituent
A group selected from the group consisting of lower alkyl groups which may have
A phenyl lower alkenyl group which may have
R¹, R^Two, M, n and r are the same as defined above.
The quinoxaline derivative represented by (1) or a salt thereof.

(167) R ³ represents a lower alkanoyl group,
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ⁴ represents a lower alkenyl group, and R ¹ , R ² , m, n and r are the same as described above.

(168) R ³ represents a lower alkoxycarbonyl group, R ⁴ represents a lower alkenyl group, R ¹ , R ² ,
m, n and r are the same as described above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(169) R ³ represents a lower alkanoyl group,
R ⁴ represents cycloalkyl-lower alkyl group, R ^1, R
^2. A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as described above.

(170) R ³ represents a lower alkoxycarbonyl group, R ⁴ represents a cycloalkyl lower alkyl group,
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ¹ , R ² , m, n and r are the same as described above.

(171) R ³ represents a lower alkanoyl group,
R ⁴ represents a naphthyl lower alkyl group, R ¹ , R ² ,
m, n and r are the same as described above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

[0284] (172) R ³ represents a lower alkoxycarbonyl group, R ⁴ represents a naphthyl lower alkyl group, R ^1,
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ² , m, n and r are the same as described above.

(173) R ³ represents a lower alkanoyl group;
R ⁴ represents a phenylthio-substituted lower alkyl group which may have a lower alkoxy group as a substituent on the phenyl ring, and R ¹ , R ² , m, n and r are represented by the same general formula (1) as described above. Quinoxaline derivative or a salt thereof.

(174) R ³ represents a lower alkoxycarbonyl group, R ⁴ represents a phenylthio-substituted lower alkyl group which may have a lower alkoxy group as a substituent on a phenyl ring, and R ¹ , R ² , m, n and r are the same as described above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(175) R ³ represents a lower alkanoyl group,
R ⁴ represents a phenylsulfinyl-substituted lower alkyl group which may have a lower alkoxy group as a substituent on the phenyl ring, and R ¹ , R ² , m, n and r are the same as those in the above-mentioned general formula (1). Or a salt thereof.

(176) R ³ represents a lower alkoxycarbonyl group; R ⁴ represents a phenylsulfinyl-substituted lower alkyl group which may have a lower alkoxy group as a substituent on a phenyl ring; R ¹ , R ² , m , N and r are the same as described above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(177) R ³ represents a lower alkanoyl group,
R ⁴ represents a phenylsulfonyl-substituted lower alkyl group which may have a lower alkoxy group as a substituent on the phenyl ring, and R ¹ , R ² , m, n and r are the same as those in the above-mentioned general formula (1). Or a salt thereof.

(178) R ³ represents a lower alkoxycarbonyl group; R ⁴ represents a phenylsulfonyl-substituted lower alkyl group which may have a lower alkoxy group as a substituent on a phenyl ring; R ¹ , R ² , m , N and r are the same as described above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(179) R ³ represents a lower alkanoyl group,
R ⁴ is a phenoxy-substituted lower alkyl group, R ^1, R
^2. A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as described above.

(180) R ³ represents a lower alkoxycarbonyl group, R ⁴ represents a phenoxy-substituted lower alkyl group,
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ¹ , R ² , m, n and r are the same as described above.

(181) R ³ represents a lower alkanoyl group;
R ⁴ represents a group represented by chemical formula 28], R ^1,
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ² , m, n and r are the same as described above.

(182) R ³ represents a lower alkoxycarbonyl group; R ⁴ represents a group represented by the above formula
¹ , a quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ² , m, n and r are the same as described above.

(183) R ³ represents a lower alkanoyl group,
R ⁴ represents a group —A ₅ —CR ⁴² R ⁴³ R ⁴⁴ (R ⁴² , R ⁴³ and R ⁴⁴
Wherein R ¹ , R ² , m, n and r are the same as defined above, or a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(184) R ³ represents a lower alkoxycarbonyl group, and R ⁴ represents a group —A ₅ —CR ⁴² R ⁴³ R ⁴⁴ (R ⁴² , R ⁴³
And R ⁴⁴ are the same as defined above), and R ¹ , R ² , m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(185) R ³ represents a lower alkanoyl group,
R ⁴ may have a group selected from the group consisting of an oxo group, a hydroxyl group and a silyloxy group having a lower alkyl group as a substituent on the 2,3-dihydro-1H-indenyl ring, -1H-indenyl group-substituted lower alkyl group; R ¹ , R ² , m, n and r
Is a quinoxaline derivative represented by the above general formula (1) or a salt thereof.

(186) R ³ represents a lower alkoxycarbonyl group, and R ⁴ represents an oxo group as a substituent, a hydroxyl group and a silyloxy group having a lower alkyl group as a substituent on a 2,3-dihydro-1H-indenyl ring. A lower alkyl group substituted with a 2,3-dihydro-1H-indenyl group which may have a group selected from the group; R ¹ , R ² , m,
n and r are the same as described above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(187) R ³ represents a lower alkanoyl group;
R ⁴ represents a group represented by chemical formula 34], R ^1,
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ² , m, n and r are the same as described above.

(188) R ³ represents a lower alkoxycarbonyl group, R ⁴ represents a group represented by the above formula,
¹ , a quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ² , m, n and r are the same as described above.

(189) R ³ is a lower alkoxy lower alkyl group and R ⁴ is a group represented by the above formula
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ¹ , R ² , m, n and r are the same as described above.

(190) R ³ is a phenoxycarbonyl group and R
⁴ represents a group represented by the above-mentioned [Chemical formula 27], and R ¹ , R ² ,
m, n and r are the same as described above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(191) R ³ represents a lower alkoxy lower alkyl group, R ⁴ is selected from the group consisting of a lower alkoxy group as a substituent, a halogen atom, a lower alkanoyl group and a phenyl lower alkenylcarbonyl group as substituents on a phenyl ring. amino group which may have a group, a lower alkoxy-substituted lower alkoxy group, a tetrazolyl group which may have a lower alkyl group as a substituent on the tetrazole ring, a hydroxyl group, a group -O-a ₄ -CO-NR ⁴⁰ R
⁴¹ (A ₄ , R ⁴⁰ and R ⁴¹ are the same as described above), phenyl which may have a group selected from the group consisting of a lower alkenyloxy group, a nitro group and a lower alkyl group which may have a halogen atom as a substituent. Represents a lower alkenyl group,
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ¹ , R ² , m, n and r are the same as described above.

(192) R ³ represents a phenoxycarbonyl group, R ⁴ is selected from the group consisting of a lower alkoxy group as a substituent, a halogen atom, a lower alkanoyl group and a phenyl lower alkenylcarbonyl group as substituents on the phenyl ring. An amino group that may have a group, a lower alkoxy group-substituted lower alkoxy group, a tetrazolyl group that may have a lower alkyl group as a substituent on the tetrazole ring,
Hydroxyl, group _{-O-A 4 -CO-N-} R 40 R 41 (A 4, R
⁴⁰ and R ⁴¹ are the same as described above), a lower alkenyloxy group,
A phenyl lower alkenyl group which may have a group selected from the group consisting of a nitro group and a lower alkyl group which may have a halogen atom as a substituent; R ¹ , R ² ,
m, n and r are the same as described above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(193) R ³ represents a lower alkoxy lower alkyl group, R ⁴ represents a lower alkenyl group, R ¹ ,
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ² , m, n and r are the same as described above.

(194) R ³ represents a phenoxycarbonyl group, R ⁴ represents a lower alkenyl group, R ¹ , R ² , m,
n and r are the same as described above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(195) R ³ represents a lower alkoxy lower alkyl group, R ⁴ represents a cycloalkyl lower alkyl group, and R ¹ , R ² , m, n and r are the same as defined in the above general formula (1) Or a salt thereof.

(196) R ³ represents a phenoxycarbonyl group, R ⁴ represents a cycloalkyl lower alkyl group,
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ¹ , R ² , m, n and r are the same as described above.

(197) R ³ represents a lower alkoxy lower alkyl group, R ⁴ represents a naphthyl lower alkyl group,
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ¹ , R ² , m, n and r are the same as described above.

[0310] (198) R ³ represents a phenoxycarbonyl group, R ⁴ represents a naphthyl lower alkyl group, R ^1,
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ² , m, n and r are the same as described above.

(199) R ³ represents a lower alkoxy lower alkyl group; R ⁴ represents a phenylthio-substituted lower alkyl group which may have a lower alkoxy group as a substituent on a phenyl ring; R ¹ , R ² , m , N and r are the same as described above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(200) R ³ represents a phenoxycarbonyl group; R ⁴ represents a phenylthio-substituted lower alkyl group which may have a lower alkoxy group as a substituent on a phenyl ring; R ¹ , R ² , m, n And r are the same as described above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(201) R ³ represents a lower alkoxy lower alkyl group, R ⁴ represents a phenylsulfinyl-substituted lower alkyl group which may have a lower alkoxy group as a substituent on a phenyl ring, R ¹ , R ² , m, n and r are the same as described above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(202) R ³ represents a phenoxycarbonyl group, R ⁴ represents a phenylsulfinyl-substituted lower alkyl group which may have a lower alkoxy group as a substituent on the phenyl ring, and R ¹ , R ² , m, n and r are the same as described above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(203) R ³ represents a lower alkoxy lower alkyl group, R ⁴ represents a phenylsulfonyl-substituted lower alkyl group which may have a lower alkoxy group as a substituent on a phenyl ring, and R ¹ , R ² , m, n and r are the same as described above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(204) R ³ represents a phenoxycarbonyl group, R ⁴ represents a phenylsulfonyl-substituted lower alkyl group which may have a lower alkoxy group as a substituent on a phenyl ring, and R ¹ , R ² , m, n and r are the same as described above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(205) R ³ represents a lower alkoxy lower alkyl group, R ⁴ represents a phenoxy-substituted lower alkyl group, and R ¹ , R ² , m, n and r have the same general formula (1) Or a salt thereof.

(206) R ³ represents a phenoxycarbonyl group, R ⁴ represents a phenoxy-substituted lower alkyl group,
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ¹ , R ² , m, n and r are the same as described above.

(207) R ³ represents a lower alkoxy lower alkyl group, R ⁴ represents a group represented by the above formula (28),
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ¹ , R ² , m, n and r are the same as described above.

[0320] (208) R ³ represents a phenoxycarbonyl group, a group in which R ⁴ is represented by the chemical formula 28], R ^1,
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ² , m, n and r are the same as described above.

(209) R ³ represents a lower alkoxy lower alkyl group, and R ⁴ represents a group —A ₅ —CR ⁴² R ⁴³ R ⁴⁴ (A ₅ , R
⁴² , R ⁴³ and R ⁴⁴ are the same as defined above), and R ¹ , R ² ,
m, n and r are the same as described above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(210) R ³ represents a phenoxycarbonyl group, and R ⁴ represents a group —A ₅ —CR ⁴² R ⁴³ R ⁴⁴ (A ₅ , R ⁴² , R
⁴³ and R ⁴⁴ are the same as described above), and R ¹ , R ² , m, n
And r are the same as described above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(211) R ³ represents a lower alkoxy lower alkyl group, and R ⁴ represents an oxo group, a hydroxyl group or a silyloxy group having a lower alkyl group as a substituent on a 2,3-dihydro-1H-indenyl ring. A 2,3-dihydro-1H-indenyl-substituted lower alkyl group which may have a group selected from the group consisting of R ¹ , R ² ,
m, n and r are the same as described above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

[0324] (212) R ³ represents a phenoxycarbonyl group, the group R ⁴ is a silyloxy group having a lower alkyl group as oxo group, a hydroxyl group and a substituted group as a substituent on the 2,3-dihydro -1H- indenyl ring A lower alkyl group substituted with a 2,3-dihydro-1H-indenyl group which may have a group selected from the group consisting of R ¹ , R ² , m, n and r in the above-mentioned general formula (1) Or a salt thereof.

(213) R ³ represents a lower alkoxy lower alkyl group, R ⁴ represents a group represented by the above formula
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ¹ , R ² , m, n and r are the same as described above.

[0326] (214) R ³ represents a phenoxycarbonyl group, a group in which R ⁴ is represented by the chemical formula 34], R ^1,
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ² , m, n and r are the same as described above.

(215) R ³ is a lower alkyl group substituted with a lower alkanoyl group, R ⁴ is a group represented by the above formula [Chemical Formula 27], and R ¹ , R ² , m, n and r are the same as described above. A quinoxaline derivative represented by the general formula (1) or a salt thereof.

(216) R ³ is a lower alkoxycarbonyloxy-substituted lower alkyl group, and R ⁴ is a group represented by the above formula. R ¹ , R ² , m, n and r are as defined above. A quinoxaline derivative represented by the general formula (1) or a salt thereof.

(217) A group wherein R ³ represents a lower alkanoyl group-substituted lower alkyl group, R ⁴ represents a lower alkoxy group, a halogen atom, a lower alkanoyl group or a phenyl lower alkenylcarbonyl group as a substituent on a phenyl ring. amino group which may have a more selected group, a lower alkoxy-substituted lower alkoxy group, a tetrazolyl group which may have a lower alkyl group as a substituent on the tetrazole ring, a hydroxyl group, a group -O-a ₄ -CO- NR ⁴⁰ R
⁴¹ (A ₄ , R ⁴⁰ and R ⁴¹ are the same as described above), phenyl which may have a group selected from the group consisting of a lower alkenyloxy group, a nitro group and a lower alkyl group which may have a halogen atom as a substituent. Represents a lower alkenyl group,
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ¹ , R ² , m, n and r are the same as described above.

(218) R ³ represents a lower alkoxycarbonyloxy-substituted lower alkyl group, R ⁴ represents a lower alkoxy group as a substituent, a halogen atom, a lower alkanoyl group and a phenyl lower alkenylcarbonyl group as substituents on a phenyl ring. amino group which may have a group selected from the group, a lower alkoxy-substituted lower alkoxy group, a tetrazolyl group which may have a lower alkyl group as a substituent on the tetrazole ring, a hydroxyl group, a group -O-a ₄ -C
^{O-N-R 40 R 41} (A 4, R 40 and R ⁴¹ are the same as defined above), a lower alkenyloxy group, selected from lower alkyl group consisting of which may have a halogen atom as a nitro group and a substituted group A quinoxaline derivative represented by the general formula (1) or a salt thereof, which represents a phenyl lower alkenyl group which may have a group, wherein R ¹ , R ² , m, n and r are the same as described above.

(219) R ³ represents a lower alkanoyl group-substituted lower alkyl group; R ⁴ represents a lower alkenyl group;
¹ , a quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ² , m, n and r are the same as described above.

(220) R ³ represents a lower alkoxycarbonyloxy-substituted lower alkyl group, R ⁴ represents a lower alkenyl group, and R ¹ , R ² , m, n and r have the same general formula (1) And a salt thereof.

(221) R ³ represents a lower alkanoyl-substituted lower alkyl group, R ⁴ represents a cycloalkyl lower alkyl group, and R ¹ , R ² , m, n and r have the same general formula (1) And a salt thereof.

(222) R ³ represents a lower alkoxycarbonyloxy-substituted lower alkyl group, R ⁴ represents a cycloalkyl lower alkyl group, and R ¹ , R ² , m, n and r are the same as defined above. The quinoxaline derivative represented by (1) or a salt thereof.

(223) R ³ represents a lower alkanoyl group-substituted lower alkyl group, R ⁴ represents a naphthyl lower alkyl group, and R ¹ , R ² , m, n and r have the same general formula (1) And a salt thereof.

(224) R ³ represents a lower alkoxycarbonyloxy-substituted lower alkyl group, R ⁴ represents a naphthyl lower alkyl group, and R ¹ , R ² , m, n and r have the same general formula (I) A quinoxaline derivative or a salt thereof represented by 1).

(225) R ³ represents a lower alkanoyl-substituted lower alkyl group; R ⁴ represents a phenylthio-substituted lower alkyl group which may have a lower alkoxy group as a substituent on a phenyl ring; R ¹ and R ² , M, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

[0338] (226) R ³ represents a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenylthio substituted lower alkyl group wherein R ⁴ which may have a lower alkoxy group as a substituent on the phenyl ring, R ^1, R ² , m,
n and r are the same as described above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

[0339] (227) R ³ is a lower alkanoyl-substituted lower alkyl group, a phenylsulfinyl-substituted lower alkyl group which may R ⁴ has a lower alkoxy group as a substituent on the phenyl ring, R ^1, R ^2. A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as described above.

[0340] (228) R ³ represents a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenylsulfinyl-substituted lower alkyl group which may R ⁴ has a lower alkoxy group as a substituent on the phenyl ring, R ^1, R
^2. A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as described above.

[0341] (229) R ³ is a lower alkanoyl-substituted lower alkyl group, a phenylsulfonyl-substituted lower alkyl group wherein R ⁴ which may have a lower alkoxy group as a substituent on the phenyl ring, R ^1, R ^2. A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as described above.

[0342] (230) R ³ represents a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenylsulfonyl-substituted lower alkyl group wherein R ⁴ which may have a lower alkoxy group as a substituent on the phenyl ring, R ^1,
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ² , m, n and r are the same as described above.

(231) R ³ represents a lower alkanoyl group-substituted lower alkyl group, R ⁴ represents a phenoxy-substituted lower alkyl group, and R ¹ , R ² , m, n and r have the same general formula (I) A quinoxaline derivative or a salt thereof represented by 1).

(232) R ³ represents a lower alkoxycarbonyloxy-substituted lower alkyl group, R ⁴ represents a phenoxy-substituted lower alkyl group, and R ¹ , R ² , m, n and r are the same as defined above. The quinoxaline derivative represented by (1) or a salt thereof.

(233) R ³ represents a lower alkanoyl group-substituted lower alkyl group, R ⁴ represents a group represented by the above formula, and R ¹ , R ² , m, n and r are as defined above. A quinoxaline derivative represented by a general formula (1) or a salt thereof.

(234) R ³ represents a lower alkoxycarbonyloxy-substituted lower alkyl group, and R ⁴ represents the above
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ¹ , R ² , m, n and r are the same as described above.

(235) R ³ represents a lower alkyl group substituted with a lower alkanoyl group, and R ⁴ represents a group —A ₅ —CR ⁴² R ⁴³ R
⁴⁴ (A ₅ , R ⁴² , R ⁴³ and R ⁴⁴ are as defined above),
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ¹ , R ² , m, n and r are the same as described above.

(236) R ³ represents a lower alkoxycarbonyloxy-substituted lower alkyl group, and R ⁴ represents a group —A ₅ —CR
⁴² R ⁴³ R ⁴⁴ (A ₅ , R ⁴² , R ⁴³ and R ⁴⁴ are as defined above)
Wherein R ¹ , R ² , m, n and r are as defined above, or a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(237) R ³ represents a lower alkanoyl group-substituted lower alkyl group, and R ⁴ has an oxo group, a hydroxyl group and a lower alkyl group as a substituent on the 2,3-dihydro-1H-indenyl ring. 2,3-dihydro- which may have a group selected from the group consisting of silyloxy groups
Indicates 1H- indenyl group substituted lower alkyl group, R ^1,
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ² , m, n and r are the same as described above.

(238) R ³ represents a lower alkoxycarbonyloxy-substituted lower alkyl group, and R ⁴ represents an oxo group as a substituent, a hydroxyl group and a lower alkyl group as a substituent on a 2,3-dihydro-1H-indenyl ring. 2,3 which may have a group selected from the group consisting of silyloxy groups
A quinoxaline derivative represented by the general formula (1) or a salt thereof, which represents a -dihydro-1H-indenyl-substituted lower alkyl group, wherein R ¹ , R ² , m, n and r are the same as described above.

(239) R ³ represents a lower alkyl group substituted with a lower alkanoyl group, R ⁴ represents a group represented by the above formula, and R ¹ , R ² , m, n and r are the same as those described above. A quinoxaline derivative represented by a general formula (1) or a salt thereof.

(240) R ³ represents a lower alkoxycarbonyloxy-substituted lower alkyl group, and R ⁴ represents the above
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ¹ , R ² , m, n and r are the same as described above.

(241) R ³ is a benzoyl-substituted lower alkyl group which may have a halogen atom as a substituent on the phenyl ring, and R ⁴ is a group represented by the above formula [Chem. 27], and R ¹ and R ² , M, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(242) R ³ is a group represented by -E-NR ⁵² R ⁵³ (E, R
⁵² and R ⁵³ are the same as described above), and R ⁴ is as defined above.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ¹ , R ² , m, n and r are the same as defined above.

(243) R ³ represents a benzoyl-substituted lower alkyl group which may have a halogen atom as a substituent on the phenyl ring, and R ⁴ represents a lower alkoxy group, a halogen atom or a substituent as a substituent on the phenyl ring. An amino group, which may have a group selected from the group consisting of a lower alkanoyl group and a phenyl lower alkenylcarbonyl group, a lower alkoxy group, a substituted lower alkoxy group, and a tetrazolyl group, which may have a lower alkyl group as a substituent on the tetrazole ring , hydroxyl, groups ^{_{-O-A 4 -CO-NR 40}} R 41
(A ₄ , R ⁴⁰ and R ⁴¹ are the same as described above), lower alkenyloxy group, nitro group and phenyl lower group which may have a group selected from the group consisting of a lower alkyl group which may have a halogen atom as a substituent. An alkenyl group;
¹ , a quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ² , m, n and r are the same as described above.

(244) R ³ is a group -E-NR ⁵² R ⁵³ (E, R
⁵² and R ⁵³ are the same as described above), and R ⁴ has a group selected from the group consisting of a lower alkoxy group as a substituent, a halogen atom, a lower alkanoyl group and a phenyl lower alkenylcarbonyl group as a substituent on a phenyl ring. Certain amino groups, lower alkoxy group-substituted lower alkoxy groups,
Tetrazolyl group which may have a lower alkyl group as a substituent on the tetrazole ring, a hydroxyl group, a group -O-A ₄ -
^{CO-N-R 40 R 41} (A 4, R 40 and R ⁴¹ are the same as defined above), a lower alkenyloxy group, selected from lower alkyl group consisting of which may have a halogen atom as a nitro group and a substituted group A quinoxaline derivative represented by the general formula (1) or a salt thereof, which represents a phenyl lower alkenyl group which may have a group, wherein R ¹ , R ² , m, n and r are the same as described above.

(245) R ³ represents a benzoyl-substituted lower alkyl group which may have a halogen atom as a substituent on the phenyl ring, R ⁴ represents a lower alkenyl group,
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ¹ , R ² , m, n and r are the same as described above.

(246) R ³ is a group represented by -E-NR ⁵² R ⁵³ (E, R
⁵² and R ⁵³ are the same as defined above), R ⁴ is a lower alkenyl group, and R ¹ , R ² , m, n and r are the same as defined above, and the quinoxaline derivative represented by the general formula (1) or a quinoxaline derivative thereof salt.

(247) R ³ represents a benzoyl-substituted lower alkyl group which may have a halogen atom as a substituent on the phenyl ring, R ⁴ represents a cycloalkyl lower alkyl group, and R ¹ , R ² , m, n and r are the same as described above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(248) R ³ is a group -E-NR ⁵² R ⁵³ (E, R
⁵² and R ⁵³ are the same as defined above), R ⁴ is a cycloalkyl lower alkyl group, and R ¹ , R ² , m, n and r are the same as defined above, and the quinoxaline derivative represented by the general formula (1) Or a salt thereof.

(249) R ³ represents a benzoyl-substituted lower alkyl group which may have a halogen atom as a substituent on the phenyl ring, R ⁴ represents a naphthyl lower alkyl group, R ¹ , R ² , m, n And r are the same as described above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(250) R ³ is a group represented by -E-NR ⁵² R ⁵³ (E, R
⁵² and R ⁵³ are the same as defined above), R ⁴ is a naphthyl lower alkyl group, and R ¹ , R ² , m, n and r are the same as defined above, or a quinoxaline derivative represented by the general formula (1) or Its salt.

(251) R ³ represents a benzoyl-substituted lower alkyl group which may have a halogen atom as a substituent on the phenyl ring, and R ⁴ represents a phenylthio group which may have a lower alkoxy group as a substituent on the phenyl ring. A quinoxaline derivative represented by the general formula (1) or a salt thereof, which represents a substituted lower alkyl group, wherein R ¹ , R ² , m, n and r are the same as described above.

(252) R ³ is a group represented by -E-NR ⁵² R ⁵³ (E, R
⁵² and R ⁵³ are the same as described above), and R ⁴ represents a phenylthio-substituted lower alkyl group which may have a lower alkoxy group as a substituent on the phenyl ring, and R ¹ , R ² ,
m, n and r are the same as described above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(253) R ³ represents a benzoyl-substituted lower alkyl group which may have a halogen atom as a substituent on the phenyl ring, and R ⁴ represents a phenyl which may have a lower alkoxy group as a substituent on the phenyl ring. A quinoxaline derivative represented by the general formula (1) or a salt thereof, which represents a sulfinyl-substituted lower alkyl group, and wherein R ¹ , R ² , m, n and r are the same as described above.

(254) R ³ is a group represented by -E-NR ⁵² R ⁵³ (E, R
⁵² and R ⁵³ have the same) above, shows a phenylsulfinyl-substituted lower alkyl group which may R ⁴ has a lower alkoxy group as a substituent on the phenyl ring, R ^1,
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ² , m, n and r are the same as described above.

(255) R ³ represents a benzoyl-substituted lower alkyl group which may have a halogen atom as a substituent on the phenyl ring, and R ⁴ is a phenyl which may have a lower alkoxy group as a substituent on the phenyl ring. Represents a sulfonyl-substituted lower alkyl group, R ¹ , R ² , m, n and r
Is a quinoxaline derivative represented by the above general formula (1) or a salt thereof.

(256) R ³ is a group represented by -E-NR ⁵² R ⁵³ (E, R
⁵² and R ⁵³ have the same) above, a phenyl sulfonyl-substituted lower alkyl group wherein R ⁴ which may have a lower alkoxy group as a substituent on the phenyl ring, R ^1, R
^2. A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as described above.

(257) R ³ represents a benzoyl-substituted lower alkyl group which may have a halogen atom as a substituent on the phenyl ring, R ⁴ represents a phenoxy-substituted lower alkyl group, and R ¹ , R ² , m, n and r are the same as described above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(258) R ³ is a group represented by -E-NR ⁵² R ⁵³ (E, R
⁵² and R ⁵³ are the same as described above), R ⁴ is a phenoxy-substituted lower alkyl group, and R ¹ , R ² , m, n and r are the same as defined above, and are quinoxaline derivatives represented by the general formula (1) Or a salt thereof.

[0371] (259) R ³ represents a benzoyl-substituted lower alkyl group which may have a halogen atom as a substituent on the phenyl ring, represents a group R ⁴ is represented by the chemical formula 28], R ^1, R ^2. A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as described above.

(260) R ³ is a group represented by -E-NR ⁵² R ⁵³ (E, R
⁵² and R ⁵³ are the same as described above), and R ⁴ is as defined above.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ¹ , R ² , m, n and r are the same as defined above.

(261) R ³ represents a benzoyl-substituted lower alkyl group which may have a halogen atom as a substituent on the phenyl ring, and R ⁴ represents a group —A ₅ —CR ⁴² R ⁴³ R ⁴⁴ (A
₅ , R ⁴² , R ⁴³ and R ⁴⁴ are the same as defined above), and R ¹ ,
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ² , m, n and r are the same as described above.

(262) R ³ is a group represented by -E-NR ⁵² R ⁵³ (E, R
⁵² and R ⁵³ are the same as described above), and R ⁴ represents a group —A ₅ —C
R ⁴² R ⁴³ R ⁴⁴ (A ₅ , R ⁴² , R ⁴³ and R ⁴⁴ are the same as described above), and R ¹ , R ² , m, n and r are represented by the same general formula (1) as described above. Quinoxaline derivative or a salt thereof.

(263) R ³ represents a benzoyl-substituted lower alkyl group which may have a halogen atom as a substituent on the phenyl ring, and R ⁴ represents oxo as a substituent on the 2,3-dihydro-1H-indenyl ring. 2,3-dihydro-1 which may have a group selected from the group consisting of a group, a hydroxyl group and a silyloxy group having a lower alkyl group as a substituent
H- indenyl group substituted lower alkyl group, R ^1, R
^2. A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as described above.

(264) R ³ is a group represented by —E-NR ⁵² R ⁵³ (E, R
⁵² and R ⁵³ are the same as described above), wherein R ⁴ is an oxo group as a substituent on the 2,3-dihydro-1H-indenyl ring;
2, which may have a group selected from the group consisting of a silyloxy group having a hydroxyl group and a lower alkyl group as a substituent,
A quinoxaline derivative represented by the general formula (1) or a salt thereof, which represents a lower alkyl group substituted with a 3-dihydro-1H-indenyl group, wherein R ¹ , R ² , m, n and r are the same as described above.

[0377] (265) R ³ represents a benzoyl-substituted lower alkyl group which may have a halogen atom as a substituent on the phenyl ring, represents a group R ⁴ is represented by the chemical formula 34], R ^1, R ^2. A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as described above.

(266) R ³ is a group represented by -E-NR ⁵² R ⁵³ (E, R
⁵² and R ⁵³ are the same as described above), and R ⁴ is as defined above.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ¹ , R ² , m, n and r are the same as defined above.

(267) R ³ represents a group represented by the above [Chemical Formula 26]; R ⁴ represents a group represented by the above [Chemical Formula 27];
¹ , a quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ² , m, n and r are the same as described above.

(268) R ³ represents a group represented by the above formula, R ⁴ represents a lower alkoxy group as a substituent, a halogen atom, a lower alkanoyl group or a phenyl lower alkenylcarbonyl group as a substituent on a phenyl ring. amino group which may have a made a group selected from the group, a lower alkoxy-substituted lower alkoxy group, a tetrazolyl group which may have a lower alkyl group as a substituent on the tetrazole ring, a hydroxyl group, a group -O-a ₄ - ^{CO-NR 40 R 41 (A} 4,
R ⁴⁰ and R ⁴¹ are the same as defined above), a lower alkenyloxy group, a nitro group and a phenyl lower alkenyl group which may have a group selected from the group consisting of a lower alkyl group which may have a halogen atom as a substituent. , R ¹ , R
^2. A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as described above.

(269) R ³ represents a group represented by the above formula, R ⁴ represents a lower alkenyl group, R ¹ , R ² ,
m, n and r are the same as described above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(270) R ³ represents a group represented by the above formula, R ⁴ represents a cycloalkyl lower alkyl group,
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ¹ , R ² , m, n and r are the same as described above.

(271) R ³ represents a group represented by the above formula, R ⁴ represents a naphthyl lower alkyl group, R ¹ ,
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ² , m, n and r are the same as described above.

[0384] (272) R ³ represents a group represented by chemical formula 26] shows a phenylthio substituted lower alkyl group wherein R ⁴ which may have a lower alkoxy group as a substituent on the phenyl ring, R ^1, A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ² , m, n and r are the same as described above.

[0385] (273) R ³ represents a group represented by chemical formula 26] shows a phenylsulfinyl-substituted lower alkyl group which may R ⁴ has a lower alkoxy group as a substituent on the phenyl ring, R ¹ , R ² , m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

[0386] (274) R ³ represents a group represented by chemical formula 26], a phenyl sulfonyl-substituted lower alkyl group wherein R ⁴ which may have a lower alkoxy group as a substituent on the phenyl ring, R ¹ , R ² , m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(275) R ³ represents a group represented by the above-mentioned [Formula 26], R ⁴ represents a phenoxy-substituted lower alkyl group,
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ¹ , R ² , m, n and r are the same as described above.

(276) R ³ represents a group represented by the above [Chemical Formula 26]; R ⁴ represents a group represented by the above [Chemical Formula 28];
¹ , a quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ² , m, n and r are the same as described above.

(277) R ³ represents a group represented by the above formula [Chemical Formula 26], and R ⁴ represents a group -A ₅ -CR ⁴² R ⁴³ R ⁴⁴ (A ₅ ,
R ⁴² , R ⁴³ and R ⁴⁴ are the same as defined above), and R ¹ ,
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ² , m, n and r are the same as described above.

(278) R ³ is a group represented by the above formula [Chemical Formula 26], and R ⁴ is an oxo group, a hydroxyl group or a lower alkyl group as a substituent on the 2,3-dihydro-1H-indenyl ring. A 2,3-dihydro-1H-indenyl-substituted lower alkyl group which may have a group selected from the group consisting of a silyloxy group having R ¹ , R ² , m,
n and r are the same as described above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(279) R ³ represents a group represented by the above [Chemical Formula 26]; R ⁴ represents a group represented by the above [Chemical Formula 34];
¹ , a quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ² , m, n and r are the same as described above.

(280) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (4), R ³
And R ⁴ is as defined in the above (9) or (10), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(281) R ¹ is (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (4), R ³
And R ⁴ is as defined in the above (11) or (12), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(282) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (4), R ³
And R ⁴ is as defined in the above (13) or (14), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(283) R ¹ is (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (4), R ³
And R ⁴ is as defined in the above (15) or (16), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(284) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (4), R ³
And R ⁴ is as defined in the above (17) or (18), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(285) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (4), R ³
And R ⁴ is as defined in the above (17) or (18), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(286) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (4), R ³
And R ⁴ is as defined in the above (19) or (20), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(287) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (4), R ³
And R ⁴ is as defined in the above (21) or (22), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(288) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (4), R ³
And R ⁴ is as defined in the above (23) or (24), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(289) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (4), R ³
And R ⁴ is as defined in the above (25) or (26), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(290) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (4), R ³
And R ⁴ is as defined in the above (27) or (28), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(291) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (4), R ³
And R ⁴ is as defined in the above (29) or (30), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(292) R ¹ is (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (4), R ³
And R ⁴ is as defined in the above (31) or (32), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(293) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (4), R ³
And R ⁴ is as defined in the above (33) or (34), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(294) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (4), R ³
And R ⁴ is as defined in the above (35), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(295) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (5), R ³
And R ⁴ is as defined in the above (9) or (10), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(296) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (5), R ³
And R ⁴ is as defined in the above (11) or (12), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(297) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (5), R ³
And R ⁴ is as defined in the above (13) or (14), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(298) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (5), R ³
And R ⁴ is as defined in the above (15) or (16), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(299) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (5), R ³
And R ⁴ is as defined in the above (17) or (18), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(300) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (5), R ³
And R ⁴ is as defined in the above (19) or (20), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(301) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (5), R ³
And R ⁴ is as defined in the above (21) or (22), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(302) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (5), R ³
And R ⁴ is as defined in the above (23) or (24), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(303) R ¹ is as defined above in (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (5), R ³
And R ⁴ is as defined in the above (25) or (26), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(304) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (5), R ³
And R ⁴ is as defined in the above (27) or (28), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(305) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (5), R ³
And R ⁴ is as defined in the above (29) or (30), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(306) R ¹ is (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (5), R ³
And R ⁴ is as defined in the above (31) or (32), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(307) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (5), R ³
And R ⁴ is as defined in the above (33) or (34), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(308) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (5), R ³
And R ⁴ is as defined in the above (35), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(309) R ¹ is as defined above in (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (6), R ³
And R ⁴ is as defined in the above (9) or (10), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(310) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (6), R ³
And R ⁴ is as defined in the above (11) or (12), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(311) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (6), R ³
And R ⁴ is as defined in the above (13) or (14), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(312) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (6), R ³
And R ⁴ is as defined in the above (15) or (16), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(313) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (6), R ³
And R ⁴ is as defined in the above (17) or (18), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(314) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (6), R ³
And R ⁴ is as defined in the above (19) or (20), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(315) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (6), R ³
And R ⁴ is as defined in the above (21) or (22), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(316) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (6), R ³
And R ⁴ is as defined in the above (23) or (24), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(317) R ¹ is as defined above in (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (6), R ³
And R ⁴ is as defined in the above (25) or (26), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(318) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (6), R ³
And R ⁴ is as defined in the above (27) or (28), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(319) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (6), R ³
And R ⁴ is as defined in the above (29) or (30), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(320) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (6), R ³
And R ⁴ is as defined in the above (31) or (32), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(321) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (6), R ³
And R ⁴ is as defined in the above (33) or (34), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(322) R ¹ is as defined above in (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (6), R ³
And R ⁴ is as defined in the above (35), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(323) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (7), R ³
And R ⁴ is as defined in the above (9) or (10), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(324) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (7), R ³
And R ⁴ is as defined in the above (11) or (12), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(325) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (7), R ³
And R ⁴ is as defined in the above (13) or (14), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(326) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (7), R ³
And R ⁴ is as defined in the above (15) or (16), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(327) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (7), R ³
And R ⁴ is as defined in the above (17) or (18), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(328) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (7), R ³
And R ⁴ is as defined in the above (19) or (20), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(329) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (7), R ³
And R ⁴ is as defined in the above (21) or (22), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(330) R ¹ is as defined above in (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (7), R ³
And R ⁴ is as defined in the above (23) or (24), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(331) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (7), R ³
And R ⁴ is as defined in the above (25) or (26), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(332) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (7), R ³
And R ⁴ is as defined in the above (27) or (28), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(333) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (7), R ³
And R ⁴ is as defined in the above (29) or (30), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(334) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (7), R ³
And R ⁴ is as defined in the above (31) or (32), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(335) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (7), R ³
And R ⁴ is as defined in the above (33) or (34), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(336) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (7), R ³
And R ⁴ is as defined in the above (35), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(337) R ¹ is as defined above in (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (8), R ³
And R ⁴ is as defined in the above (9) or (10), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(338) R ¹ is as defined above in (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (8), R ³
And R ⁴ is as defined in the above (11) or (12), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(339) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (8), R ³
And R ⁴ is as defined in the above (13) or (14), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(340) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (8), R ³
And R ⁴ is as defined in the above (15) or (16), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(341) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (8), R ³
And R ⁴ is as defined in the above (17) or (18), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(342) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (8), R ³
And R ⁴ is as defined in the above (19) or (20), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(343) R ¹ is as defined above in (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (8), R ³
And R ⁴ is as defined in the above (21) or (22), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(344) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (8), R ³
And R ⁴ is as defined in the above (23) or (24), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(345) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (8), R ³
And R ⁴ is as defined in the above (25) or (26), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(346) R ¹ is as defined above in (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (8), R ³
And R ⁴ is as defined in the above (27) or (28), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(347) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (8), R ³
And R ⁴ is as defined in the above (29) or (30), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(348) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (8), R ³
And R ⁴ is as defined in the above (31) or (32), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(349) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (8), R ³
And R ⁴ is as defined in the above (33) or (34), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(350) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (8), R ³
And R ⁴ is as defined in the above (35), and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(351) R ¹ is the same as defined in the above (1), and R ³
And R ⁴ are (137), (138), (163), (164), (18)
9), (190), (215), (216), (241), (242) or (26)
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ² , m, n and r are the same as defined above.

(352) R ¹ is the same as defined in the above (1), and R ³
And R ⁴ are (139), (140), (165), (166), (19)
1), (192), (217), (218), (243), (244) or (26)
8) wherein R ² , m, n and r are the same as defined above, or a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(353) R ¹ is the same as defined in the above (1), and R ³
And R ⁴ are (141), (142), (167), (168), (19)
3), (194), (219), (220), (245), (246) or (26)
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ² , m, n and r are the same as defined above.

(354) R ¹ is the same as defined in the above (1), and R ³
And R ⁴ are (143), (144), (169), (170), (19)
5), (196), (221), (222), (247), (248) or (27)
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ² , m, n and r are the same as defined above.

(355) R ¹ is the same as defined in the above (1), and R ³
And R ⁴ are (145), (146), (171), (172), (19)
7), (198), (223), (224), (249), (250) or (27)
A quinoxaline derivative represented by the general formula (1), wherein R ² , m, n and r are the same as defined above, or a salt thereof.

(356) R ¹ is the same as defined in the above (1), and R ³
And R ⁴ are (147), (148), (173), (174), (19)
9), (200), (225), (226), (251), (252) or (27)
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ² , m, n and r are the same as defined above.

(357) R ¹ is the same as defined in the above (1), and R ³
And R ⁴ are as defined in the above (149), (150), (175), (176), (20)
1), (202), (227), (228), (253), (254) or (27)
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ² , m, n and r are the same as defined above.

(358) R ¹ is the same as defined in the above (1), and R ³
And R ⁴ are (151), (152), (177), (178), (20)
3), (204), (229), (230), (255), (256), or (27)
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ² , m, n and r are the same as defined above.

(359) R ¹ is the same as defined in the above (1), and R ³
And R ⁴ are (153), (154), (179), (180), (20)
5), (206), (231), (232), (257), (258) or (27)
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ² , m, n and r are the same as defined above.

(360) R ¹ represents the definition of the above (1), and R ³
And R ⁴ are (155), (156), (181), (182), (20)
7), (208), (233), (234), (259), (260) or (27)
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ² , m, n and r are the same as defined above.

(361) R ¹ is the same as defined in the above (1), and R ³
And R ⁴ are as defined above in (157), (158), (183), (184), (20)
9), (210), (235), (236), (261), (262) or (27)
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ² , m, n and r are the same as defined above.

(362) R ¹ is the same as defined in the above (1), and R ³
And R ⁴ are as defined in (159), (160), (185), (186), and (21).
1), (212), (237), (238), (263), (264) or (27)
8) wherein R ² , m, n and r are the same as defined above, or a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(363) R ¹ is the same as defined in the above (1), and R ³
And R ⁴ are (161), (162), (187), (188), (21)
3), (214), (239), (240), (265), (266) or (27)
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ² , m, n and r are the same as defined above.

(364) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (4), and R ³ and R ⁴ represent the above definitions.
(137), (138), (163), (164), (189), (190), (2
15) The definition of (216), (241), (242) or (267), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(365) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (4), and R ³ and R ⁴ represent the above definitions.
(139), (140), (165), (166), (191), (192), (2
A quinoxaline derivative represented by the general formula (1), wherein m, n and r are the same as defined above, wherein quinoxaline derivative or a salt thereof is defined.

(366) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (4), and R ³ and R ⁴ represent the above definitions.
(141), (142), (167), (168), (193), (194), (2
19) The definition of (220), (245), (246) or (269), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(367) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (4), and R ³ and R ⁴ represent the above definitions.
(143), (144), (169), (170), (195), (196), (2
21) The definition of (222), (247), (248) or (270), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(368) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (4), and R ³ and R ⁴ represent the above definitions.
(145), (146), (171), (172), (197), (198), (2
23) The definition of (224), (249), (250) or (271), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(369) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (4), and R ³ and R ⁴ represent the above definitions.
(147), (148), (173), (174), (199), (200), (2
25) The definition of (226), (251), (252) or (272), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(370) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (4), and R ³ and R ⁴ represent the above definitions.
(149), (150), (175), (176), (201), (202), (2
27) The definition of (228), (253), (254) or (273), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(371) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (4), and R ³ and R ⁴ represent the above definitions.
(151), (152), (177), (178), (203), (204), (2
29) The definition of (230), (255), (256) or (274), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(372) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (4), and R ³ and R ⁴ represent the above definitions.
(153), (154), (179), (180), (205), (206), (2
31) The definition of (232), (257), (258) or (275), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(373) R¹Indicates the definition of (2) or (3) above.
Then R^TwoRepresents the definition of the above (4), and R ^ThreeAnd R^FourIs
(155), (156), (181), (182), (207), (208), (2
33), (234), (259), (260) or (276)
And m, n and r are represented by the same general formula (1) as described above.
Or a salt thereof.

(374) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (4), and R ³ and R ⁴ represent the above definitions.
(157), (158), (183), (184), (209), (210), (2
35) The definition of (236), (261), (262) or (277), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(375) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (4), and R ³ and R ⁴ represent the above definitions.
(159), (160), (185), (186), (211), (212), (2
37) The definition of (238), (263), (264) or (278), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(376) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (4), and R ³ and R ⁴ represent the above definitions.
(161), (162), (187), (188), (213), (214), (2
39) The definition of (240), (265), (266) or (279), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(377) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (5), and R ³ and R ⁴ represent the above definitions.
(137), (138), (163), (164), (189), (190), (2
15) The definition of (216), (241), (242) or (267), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(378) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (5), and R ³ and R ⁴ represent the above definitions.
(139), (140), (165), (166), (191), (192), (2
A quinoxaline derivative represented by the general formula (1), wherein m, n and r are the same as defined above, wherein quinoxaline derivative or a salt thereof is defined.

(379) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (5), and R ³ and R ⁴ represent the above definitions.
(141), (142), (167), (168), (193), (194), (2
19) The definition of (220), (245), (246) or (269), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(380) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (5), and R ³ and R ⁴ represent the above definitions.
(143), (144), (169), (170), (195), (196), (2
21) The definition of (222), (247), (248) or (270), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(381) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (5), and R ³ and R ⁴ represent the above definitions.
(145), (146), (171), (172), (197), (198), (2
23) The definition of (224), (249), (250) or (271), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(382) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (5), and R ³ and R ⁴ represent the above definitions.
(147), (148), (173), (174), (199), (200), (2
25) The definition of (226), (251), (252) or (272), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(383) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (5), and R ³ and R ⁴ represent the above definitions.
(149), (150), (175), (176), (201), (202), (2
27) The definition of (228), (253), (254) or (273), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(384) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (5), and R ³ and R ⁴ represent the above definitions.
(151), (152), (177), (178), (203), (204), (2
29) The definition of (230), (255), (256) or (274), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(385) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (5), and R ³ and R ⁴ represent the above definitions.
(153), (154), (179), (180), (205), (206), (2
31) The definition of (232), (257), (258) or (275), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(386) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (5), and R ³ and R ⁴ represent the above definitions.
(155), (156), (181), (182), (207), (208), (2
33) The definition of (234), (259), (260) or (276), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(387) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (5), and R ³ and R ⁴ represent the above definitions.
(157), (158), (183), (184), (209), (210), (2
35) The definition of (236), (261), (262) or (277), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(388) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (5), and R ³ and R ⁴ represent the above definitions.
(159), (160), (185), (186), (211), (212), (2
37) The definition of (238), (263), (264) or (278), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(389) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (5), and R ³ and R ⁴ represent the above definitions.
(161), (162), (187), (188), (213), (214), (2
39) The definition of (240), (265), (266) or (279), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(390) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (6), and R ³ and R ⁴ represent the above definitions.
(137), (138), (163), (164), (189), (190), (2
15) The definition of (216), (241), (242) or (267), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(391) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (6), and R ³ and R ⁴ represent the above definitions.
(139), (140), (165), (166), (191), (192), (2
17) The definition of 218, 243, 244 or 268, wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(392) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (6), and R ³ and R ⁴ represent the above definitions.
(141), (142), (167), (168), (193), (194), (2
19) The definition of (220), (245), (246) or (269), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(393) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (6), and R ³ and R ⁴ represent the above definitions.
(143), (144), (169), (170), (195), (196), (2
21) The definition of (222), (247), (248) or (270), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(394) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (6), and R ³ and R ⁴ represent the above definitions.
(145), (146), (171), (172), (197), (198), (2
23) The definition of (224), (249), (250) or (271), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(395) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (6), and R ³ and R ⁴ represent the above definitions.
(147), (148), (173), (174), (199), (200), (2
25) The definition of (226), (251), (252) or (272), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(396) R¹Indicates the definition of (2) or (3) above.
Then R^TwoRepresents the definition of the above (6), ^ThreeAnd R^FourIs
(149), (150), (175), (176), (201), (202), (2
27), (228), (253), (254) or (273)
And m, n and r are represented by the same general formula (1) as described above.
Or a salt thereof.

(397) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (6), and R ³ and R ⁴ represent the above definitions.
(151), (152), (177), (178), (203), (204), (2
29) The definition of (230), (255), (256) or (274), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(398) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (6), and R ³ and R ⁴ represent the above definitions.
(153), (154), (179), (180), (205), (206), (2
31) The definition of (232), (257), (258) or (275), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(399) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (6), and R ³ and R ⁴ represent the above definitions.
(155), (156), (181), (182), (207), (208), (2
33) The definition of (234), (259), (260) or (276), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(400) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (6), and R ³ and R ⁴ represent the above definitions.
(157), (158), (183), (184), (209), (210), (2
35) The definition of (236), (261), (262) or (277), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(401) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (6), and R ³ and R ⁴ represent the above definitions.
(159), (160), (185), (186), (211), (212), (2
37) The definition of (238), (263), (264) or (278), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(402) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (6), and R ³ and R ⁴ represent the above definitions.
(161), (162), (187), (188), (213), (214), (2
39) The definition of (240), (265), (266) or (279), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(403) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (7), and R ³ and R ⁴ represent the above definitions.
(137), (138), (163), (164), (189), (190), (2
15) The definition of (216), (241), (242) or (267), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(404) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (7), and R ³ and R ⁴ represent the above definitions.
(139), (140), (165), (166), (191), (192), (2
A quinoxaline derivative represented by the general formula (1), wherein m, n and r are the same as defined above, wherein quinoxaline derivative or a salt thereof is defined.

(405) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (7), and R ³ and R ⁴ represent the above definitions.
(141), (142), (167), (168), (193), (194), (2
19) The definition of (220), (245), (246) or (269), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(406) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (7), and R ³ and R ⁴ represent the above definitions.
(143), (144), (169), (170), (195), (196), (2
21) The definition of (222), (247), (248) or (270), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(407) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (7), and R ³ and R ⁴ represent the above definitions.
(145), (146), (171), (172), (197), (198), (2
23) The definition of (224), (249), (250) or (271), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(408) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (7), and R ³ and R ⁴ represent the above definitions.
(147), (148), (173), (174), (199), (200), (2
25) The definition of (226), (251), (252) or (272), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(409) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (7), and R ³ and R ⁴ represent the above definitions.
(149), (150), (175), (176), (201), (202), (2
27) The definition of (228), (253), (254) or (273), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(410) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (7), and R ³ and R ⁴ represent the above definitions.
(151), (152), (177), (178), (203), (204), (2
29) The definition of (230), (255), (256) or (274), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(411) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (7), and R ³ and R ⁴ represent the above definitions.
(153), (154), (179), (180), (205), (206), (2
31) The definition of (232), (257), (258) or (275), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(412) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (7), and R ³ and R ⁴ represent the above definitions.
(155), (156), (181), (182), (207), (208), (2
33) The definition of (234), (259), (260) or (276), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(413) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (7), and R ³ and R ⁴ represent the above definitions.
(157), (158), (183), (184), (209), (210), (2
35) The definition of (236), (261), (262) or (277), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(414) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (7), and R ³ and R ⁴ represent the above definitions.
(159), (160), (185), (186), (211), (212), (2
37) The definition of (238), (263), (264) or (278), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(415) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (7), and R ³ and R ⁴ represent the above definitions.
(161), (162), (187), (188), (213), (214), (2
39) The definition of (240), (265), (266) or (279), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(416) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (8), and R ³ and R ⁴ represent the above definitions.
(137), (138), (163), (164), (189), (190), (2
15) The definition of (216), (241), (242) or (267), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(417) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (8), and R ³ and R ⁴ represent the above definitions.
(139), (140), (165), (166), (191), (192), (2
A quinoxaline derivative represented by the general formula (1), wherein m, n and r are the same as defined above, wherein quinoxaline derivative or a salt thereof is defined.

(418) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (8), and R ³ and R ⁴ represent the above definitions.
(141), (142), (167), (168), (193), (194), (2
19) The definition of (220), (245), (246) or (269), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(419) R¹Indicates the definition of (2) or (3) above.
Then R^TwoRepresents the definition of the above (8), ^ThreeAnd R^FourIs
(143), (144), (169), (170), (195), (196), (2
21), (222), (247), (248) or (270)
And m, n and r are represented by the same general formula (1) as described above.
Or a salt thereof.

(420) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (8), and R ³ and R ⁴ represent the above definitions.
(145), (146), (171), (172), (197), (198), (2
23) The definition of (224), (249), (250) or (271), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(421) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (8), and R ³ and R ⁴ represent the above definitions.
(147), (148), (173), (174), (199), (200), (2
25) The definition of (226), (251), (252) or (272), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(422) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (8), and R ³ and R ⁴ represent the above definitions.
(149), (150), (175), (176), (201), (202), (2
27) The definition of (228), (253), (254) or (273), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(423) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (8), and R ³ and R ⁴ represent the above definitions.
(151), (152), (177), (178), (203), (204), (2
29) The definition of (230), (255), (256) or (274), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(424) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (8), and R ³ and R ⁴ represent the above definitions.
(153), (154), (179), (180), (205), (206), (2
31) The definition of (232), (257), (258) or (275), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(425) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (8), and R ³ and R ⁴ represent the above definitions.
(155), (156), (181), (182), (207), (208), (2
33) The definition of (234), (259), (260) or (276), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(426) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (8), and R ³ and R ⁴ represent the above definitions.
(157), (158), (183), (184), (209), (210), (2
35) The definition of (236), (261), (262) or (277), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(427) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (8), and R ³ and R ⁴ represent the above definitions.
(159), (160), (185), (186), (211), (212), (2
37) The definition of (238), (263), (264) or (278), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(428) R ¹ represents the definition of the above (2) or (3), R ² represents the definition of the above (8), and R ³ and R ⁴ represent the above definitions.
(161), (162), (187), (188), (213), (214), (2
39) The definition of (240), (265), (266) or (279), wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(429) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (4), R ³
And R ⁴ are (137), (138), (163), (164), (18)
9), (190), (215), (216), (241), (242) or (26)
7) wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(430) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (4), R ³
And R ⁴ are (139), (140), (165), (166), (19)
1), (192), (217), (218), (243), (244) or (26)
8) wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(431) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (4), R ³
And R ⁴ are (141), (142), (167), (168), (19)
3), (194), (219), (220), (245), (246) or (26)
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as defined above.

(432) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (4), R ³
And R ⁴ are (143), (144), (169), (170), (19)
5), (196), (221), (222), (247), (248) or (27)
0) wherein m, n and r are the same as defined above, or a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(433) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (4), R ³
And R ⁴ are (145), (146), (171), (172), (19)
7), (198), (223), (224), (249), (250) or (27)
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as defined above.

(434) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (4), R ³
And R ⁴ are (147), (148), (173), (174), (19)
9), (200), (225), (226), (251), (252) or (27)
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as defined above.

(435) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (4), R ³
And R ⁴ are as defined in the above (149), (150), (175), (176), (20)
1), (202), (227), (228), (253), (254) or (27)
3) wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(436) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (4), R ³
And R ⁴ are (151), (152), (177), (178), (20)
3), (204), (229), (230), (255), (256), or (27)
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as defined above.

(437) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (4), R ³
And R ⁴ are (153), (154), (179), (180), (20)
5), (206), (231), (232), (257), (258) or (27)
5) The definition of 5), wherein m, n and r are the same as described above, or a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(438) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (4), R ³
And R ⁴ are (155), (156), (181), (182), (20)
7), (208), (233), (234), (259), (260) or (27)
6) wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(439) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (4), R ³
And R ⁴ are as defined above in (157), (158), (183), (184), (20)
9), (210), (235), (236), (261), (262) or (27)
7) wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(440) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (4), R ³
And R ⁴ are as defined in (159), (160), (185), (186), and (21).
1), (212), (237), (238), (263), (264) or (27)
8) wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(441) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (4), R ³
And R ⁴ are (161), (162), (187), (188), (21)
3), (214), (239), (240), (265), (266) or (27)
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as defined above.

(442) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (5), R ³
And R ⁴ are (137), (138), (163), (164), (18)
9), (190), (215), (216), (241), (242) or (26)
7) wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(443) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (5), R ³
And R ⁴ are (139), (140), (165), (166), (19)
1), (192), (217), (218), (243), (244) or (26)
8) wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(444) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (5), R ³
And R ⁴ are (141), (142), (167), (168), (19)
3), (194), (219), (220), (245), (246) or (26)
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as defined above.

(445) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (5), R ³
And R ⁴ are (143), (144), (169), (170), (19)
5), (196), (221), (222), (247), (248) or (27)
0) wherein m, n and r are the same as defined above, or a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(446) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (5), R ³
And R ⁴ are (145), (146), (171), (172), (19)
7), (198), (223), (224), (249), (250) or (27)
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as defined above.

(447) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (5), R ³
And R ⁴ are (147), (148), (173), (174), (19)
9), (200), (225), (226), (251), (252) or (27)
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as defined above.

(448) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (5), R ³
And R ⁴ are as defined in the above (149), (150), (175), (176), (20)
1), (202), (227), (228), (253), (254) or (27)
3) wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(449) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (5), R ³
And R ⁴ are (151), (152), (177), (178), (20)
3), (204), (229), (230), (255), (256), or (27)
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as defined above.

(450) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (5), R ³
And R ⁴ are (153), (154), (179), (180), (20)
5), (206), (231), (232), (257), (258) or (27)
5) The definition of 5), wherein m, n and r are the same as described above, or a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(451) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (5), R ³
And R ⁴ are (155), (156), (181), (182), (20)
7), (208), (233), (234), (259), (260) or (27)
6) wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(452) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (5), R ³
And R ⁴ are as defined above in (157), (158), (183), (184), (20)
9), (210), (235), (236), (261), (262) or (27)
7) wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(453) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (5), R ³
And R ⁴ are as defined in (159), (160), (185), (186), and (21).
1), (212), (237), (238), (263), (264) or (27)
8) wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(454) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (5), R ³
And R ⁴ are (161), (162), (187), (188), (21)
3), (214), (239), (240), (265), (266) or (27)
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as defined above.

(455) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (6), R ³
And R ⁴ are (137), (138), (163), (164), (18)
9), (190), (215), (216), (241), (242) or (26)
7) wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(456) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (6), R ³
And R ⁴ are (139), (140), (165), (166), (19)
1), (192), (217), (218), (243), (244) or (26)
8) wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(457) R ¹ is (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (6), R ³
And R ⁴ are (141), (142), (167), (168), (19)
3), (194), (219), (220), (245), (246) or (26)
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as defined above.

(458) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (6), R ³
And R ⁴ are (143), (144), (169), (170), (19)
5), (196), (221), (222), (247), (248) or (27)
0) wherein m, n and r are the same as defined above, or a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(459) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (6), R ³
And R ⁴ are (145), (146), (171), (172), (19)
7), (198), (223), (224), (249), (250) or (27)
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as defined above.

(460) R ¹ is (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (6), R ³
And R ⁴ are (147), (148), (173), (174), (19)
9), (200), (225), (226), (251), (252) or (27)
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as defined above.

(461) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (6), R ³
And R ⁴ are as defined in the above (149), (150), (175), (176), (20)
1), (202), (227), (228), (253), (254) or (27)
3) wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(462) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (6), R ³
And R ⁴ are (151), (152), (177), (178), (20)
3), (204), (229), (230), (255), (256), or (27)
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as defined above.

(463) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (6), R ³
And R ⁴ are (153), (154), (179), (180), (20)
5), (206), (231), (232), (257), (258) or (27)
5) The definition of 5), wherein m, n and r are the same as described above, or a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(464) R ¹ is (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (6), R ³
And R ⁴ are (155), (156), (181), (182), (20)
7), (208), (233), (234), (259), (260) or (27)
6) wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(465) R ¹ is as defined above in (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (6), R ³
And R ⁴ are as defined above in (157), (158), (183), (184), (20)
9), (210), (235), (236), (261), (262) or (27)
7) wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(466) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (6), R ³
And R ⁴ are as defined in (159), (160), (185), (186), and (21).
1), (212), (237), (238), (263), (264) or (27)
8) wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(467) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (6), R ³
And R ⁴ are (161), (162), (187), (188), (21)
3), (214), (239), (240), (265), (266) or (27)
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as defined above.

(468) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (7), R ³
And R ⁴ are (137), (138), (163), (164), (18)
9), (190), (215), (216), (241), (242) or (26)
7) wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(469) R ¹ is as defined above in (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (7), R ³
And R ⁴ are (139), (140), (165), (166), (19)
1), (192), (217), (218), (243), (244) or (26)
8) wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(470) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (7), R ³
And R ⁴ are (141), (142), (167), (168), (19)
3), (194), (219), (220), (245), (246) or (26)
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as defined above.

(471) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (7), R ³
And R ⁴ are (143), (144), (169), (170), (19)
5), (196), (221), (222), (247), (248) or (27)
0) wherein m, n and r are the same as defined above, or a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(472) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (7), R ³
And R ⁴ are (145), (146), (171), (172), (19)
7), (198), (223), (224), (249), (250) or (27)
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as defined above.

(473) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (7), R ³
And R ⁴ are (147), (148), (173), (174), (19)
9), (200), (225), (226), (251), (252) or (27)
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as defined above.

(474) R ¹ is (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (7), R ³
And R ⁴ are as defined in the above (149), (150), (175), (176), (20)
1), (202), (227), (228), (253), (254) or (27)
3) wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(475) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (7), R ³
And R ⁴ are (151), (152), (177), (178), (20)
3), (204), (229), (230), (255), (256), or (27)
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as defined above.

(476) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (7), R ³
And R ⁴ are (153), (154), (179), (180), (20)
5), (206), (231), (232), (257), (258) or (27)
5) The definition of 5), wherein m, n and r are the same as described above, or a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(477) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (7), R ³
And R ⁴ are (155), (156), (181), (182), (20)
7), (208), (233), (234), (259), (260) or (27)
6) wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(478) R ¹ is (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (7), R ³
And R ⁴ are as defined above in (157), (158), (183), (184), (20)
9), (210), (235), (236), (261), (262) or (27)
7) wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(479) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (7), R ³
And R ⁴ are as defined in (159), (160), (185), (186), and (21).
1), (212), (237), (238), (263), (264) or (27)
8) wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(480) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (7), R ³
And R ⁴ are (161), (162), (187), (188), (21)
3), (214), (239), (240), (265), (266) or (27)
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as defined above.

(481) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (8), R ³
And R ⁴ are (137), (138), (163), (164), (18)
9), (190), (215), (216), (241), (242) or (26)
7) wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(482) R ¹ is (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (8), R ³
And R ⁴ are (139), (140), (165), (166), (19)
1), (192), (217), (218), (243), (244) or (26)
8) wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(483) R ¹ is as defined above in (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (8), R ³
And R ⁴ are (141), (142), (167), (168), (19)
3), (194), (219), (220), (245), (246) or (26)
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as defined above.

(484) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (8), R ³
And R ⁴ are (143), (144), (169), (170), (19)
5), (196), (221), (222), (247), (248) or (27)
0) wherein m, n and r are the same as defined above, or a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(485) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (8), R ³
And R ⁴ are (145), (146), (171), (172), (19)
7), (198), (223), (224), (249), (250) or (27)
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as defined above.

(486) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (8), R ³
And R ⁴ are (147), (148), (173), (174), (19)
9), (200), (225), (226), (251), (252) or (27)
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as defined above.

(487) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (8), R ³
And R ⁴ are as defined in the above (149), (150), (175), (176), (20)
1), (202), (227), (228), (253), (254) or (27)
3) wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(488) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (8), R ³
And R ⁴ are (151), (152), (177), (178), (20)
3), (204), (229), (230), (255), (256), or (27)
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as defined above.

(489) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (8), R ³
And R ⁴ are (153), (154), (179), (180), (20)
5), (206), (231), (232), (257), (258) or (27)
5) The definition of 5), wherein m, n and r are the same as described above, or a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(490) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (8), R ³
And R ⁴ are (155), (156), (181), (182), (20)
7), (208), (233), (234), (259), (260) or (27)
6) wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(491) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (8), R ³
And R ⁴ are as defined above in (157), (158), (183), (184), (20)
9), (210), (235), (236), (261), (262) or (27)
7) wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(492) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (8), R ³
And R ⁴ are as defined in (159), (160), (185), (186), and (21).
1), (212), (237), (238), (263), (264) or (27)
8) wherein m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(493) R ¹ is as defined in the above (134), (135) or (13)
Shows the definition of 6), R ² represents a definition of the (8), R ³
And R ⁴ are (161), (162), (187), (188), (21)
3), (214), (239), (240), (265), (266) or (27)
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as defined above.

(494) m is 1, and R ¹ , R ² , R ³ ,
R ⁴ , n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(495) m is 0, and R ¹ , R ² , R ³ ,
R ⁴ , n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(496) R ¹ represents a hydrogen atom, R ² ,
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ³ , R ⁴ , m, n and r are the same as described above.

(497) R ¹ represents a halogen atom, a lower alkyl group, a lower alkoxy group, an amino group which may have a lower alkyl group as a substituent or an aminocarbonyl group which may have a lower alkyl group as a substituent. , R
² , a quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ³ , R ⁴ , m, n and r are the same as described above.

(498) R ¹ represents a hydrogen atom, R ² represents a lower alkyl group which may have a halogen atom as a substituent, and R ³ , R ⁴ , m, n and r are as defined above. A quinoxaline derivative represented by the general formula (1) or a salt thereof.

(499) R ¹ represents a hydrogen atom, R ² represents a hydrogen atom, a phenyl group, a morpholino-substituted lower alkyl group or an imidazolyl-substituted lower alkyl group, and R ³ , R ⁴ ,
m, n and r are the same as described above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(500) R ¹ represents a halogen atom, a lower alkyl group, a lower alkoxy group, an amino group which may have a lower alkyl group as a substituent or an aminocarbonyl group which may have a lower alkyl group as a substituent. , R
² represents a lower alkyl group which may have a halogen atom as a ^{substituent, R 3, R 4, m} , quinoxaline derivatives or salts thereof n and r are represented by the general formula (1) the same as above.

(501) R ¹ represents a halogen atom, a lower alkyl group, a lower alkoxy group, an amino group which may have a lower alkyl group as a substituent or an aminocarbonyl group which may have a lower alkyl group as a substituent. , R
² represents a hydrogen atom, a phenyl group, a morpholino-substituted lower alkyl group or an imidazolyl-substituted lower alkyl group,
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein R ³ , R ⁴ , m, n and r are the same as described above.

(502) R ¹ represents a hydrogen atom, R ² represents a lower alkyl group which may have a halogen atom as a substituent, R ³ represents a hydrogen atom, a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl A lower alkoxycarbonyloxy-substituted lower alkyl group, wherein R ⁴ is a group represented by the above [Chemical Formula 28] or
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as defined above.

(503) R ¹ represents a hydrogen atom, R ² represents a lower alkyl group which may have a halogen atom as a substituent, and R ³ represents a hydrogen atom, a lower alkyl group, a lower alkanoyloxy-substituted lower alkyl group A lower alkoxycarbonyl group or a lower alkoxycarbonyloxy-substituted lower alkyl group, wherein R ⁴ is a group represented by the above formula; a lower alkoxy group, a halogen atom, or a lower alkanoyl group as a substituent on a phenyl ring; And an amino group which may have a group selected from the group consisting of phenyl and lower alkenylcarbonyl groups, a lower alkoxy group, a substituted lower alkoxy group, a tetrazolyl group which may have a lower alkyl group as a substituent on the tetrazole ring, a hydroxyl group, a group ^{_{-O-a 4 -CO-NR 40}} R 41 (a 4 represents a lower alkylene group .R ⁴⁰及R ⁴¹ represents a hydrogen atom or a lower alkyl group the same or different. The R ⁴⁰ and R ^41,
These may be bonded to each other with or without the nitrogen atom to which they are bonded via another nitrogen atom or oxygen atom to form a 5- or 6-membered saturated heterocycle. ), A lower alkenyloxy group, a nitro group and a phenyl lower alkenyl group which may have a group selected from the group consisting of a lower alkyl group which may have a halogen atom as a substituent; an alkenyl group; a cycloalkyl lower alkyl group; A lower alkyl group; a phenylthio-substituted lower alkyl group which may have a lower alkoxy group as a substituent on the phenyl ring; a phenylsulfinyl-substituted lower alkyl group which may have a lower alkoxy group as a substituent on the phenyl ring; A phenylsulfonyl-substituted lower alkyl group which may have a lower alkoxy group as a substituent; a phenoxy-substituted lower alkyl group; a group -A ₅ -CR
⁴² R ⁴³ R ⁴⁴ (.R showing a wherein A ₅ represents a lower alkylene group ⁴²
And R ⁴³ together form a group = O, a group = N-OH or a lower alkylenedioxy group. R ⁴⁴ represents a phenyl group which may have a lower alkoxy group as a substituent on the phenyl ring. ) Or 2,3-dihydro-
A 2,3-dihydro-1H-indenyl-substituted lower alkyl group which may have on the 1H-indenyl ring a group selected from the group consisting of an oxo group, a hydroxyl group and a silyloxy group having a lower alkyl group as a substituent And m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(504) R ¹ represents a hydrogen atom, R ² represents a lower alkyl group which may have a halogen atom as a substituent, R ³ represents a phenyl lower alkoxycarbonyl group; a lower alkanoyl group; a lower alkoxy lower alkyl A phenoxycarbonyl group; a lower alkanoyl group-substituted lower alkyl group; a benzoyl-substituted lower alkyl group which may have a halogen atom as a substituent on the phenyl ring; a group -ER ⁵² R ⁵³ (R ⁵² and R ⁵³ are R ⁵² and R ⁵³ may be the same or different and represent a hydrogen atom, a lower alkyl group, a lower alkoxycarbonyl group or a phenyl group, and R ⁵² and R ⁵³ may be bonded to each other together with or without another nitrogen atom or oxygen atom to which they are bonded. 5 members or 6
It may form a membered saturated heterocycle. E is a lower alkylene group, a group -C (= O)-or a group -C (= O) -A- (A
Represents a lower alkylene group). ) Or is a group represented by [Chemical Formula 26], wherein R ⁴ is a group represented by the above [Chemical Formula 27]; a lower alkoxy group as a substituent, a halogen atom, a lower alkanoyl group and a phenyl An amino group which may have a group selected from the group consisting of a lower alkenylcarbonyl group, a lower alkoxy group, a substituted lower alkoxy group, a tetrazolyl group which may have a lower alkyl group as a substituent on a tetrazole ring, a hydroxyl group, a group -O —A ₄ —CO—NR ⁴⁰ R ⁴¹ (A ₄ represents a lower alkylene group; R ⁴⁰ and R ⁴¹ are the same or different and represent a hydrogen atom or a lower alkyl group; and R ⁴⁰ and R ⁴¹ are
These may be bonded to each other with or without the nitrogen atom to which they are bonded via another nitrogen atom or oxygen atom to form a 5- or 6-membered saturated heterocycle. ), A lower alkenyloxy group, a nitro group and a phenyl lower alkenyl group which may have a group selected from the group consisting of a lower alkyl group which may have a halogen atom as a substituent; an alkenyl group; a cycloalkyl lower alkyl group; A lower alkyl group; a phenylthio-substituted lower alkyl group which may have a lower alkoxy group as a substituent on the phenyl ring; a phenylsulfinyl-substituted lower alkyl group which may have a lower alkoxy group as a substituent on the phenyl ring; A phenylsulfonyl-substituted lower alkyl group which may have a lower alkoxy group as a substituent, a phenoxy-substituted lower alkyl group,
A group represented by; group _{^{-A 5 -CR 42 R 43 R 44}} ( wherein A ₅ are a lower alkylene group .R ⁴² and R ⁴³ together group = O, group = N-OH, or lower alkyl .R ⁴⁴ which shall form a dioxy group represents a phenyl group which may have a lower alkoxy group as a substituent on the phenyl ring);. as a substituent on the 2,3-dihydro -1H- indenyl ring An oxo group, a hydroxyl group and a 2,3-dihydro-1H-indenyl-substituted lower alkyl group which may have a group selected from the group consisting of a silyloxy group having a lower alkyl group as a substituent, or a compound represented by the above formula Wherein m, n and r are the same as defined above in the general formula (1)
Or a salt thereof.

(505) R ¹ represents a hydrogen atom, R ² represents a lower alkyl group which may have a halogen atom as a substituent, and R ³ and R ⁴ are formed by bonding together with the nitrogen atom to which they are bonded. 1,2,3,4-tetrahydroisoquinolyl group (which may have a lower alkoxy group as a substituent on this heterocycle), m, n and r
Is a quinoxaline derivative represented by the above general formula (1) or a salt thereof.

(506) R ¹ represents a hydrogen atom, R ² represents a hydrogen atom, a phenyl group, a morpholino-substituted lower alkyl group or an imidazolyl-substituted lower alkyl group, and R ³ represents a hydrogen atom, a lower alkanoyloxy-substituted lower alkyl group , A lower alkoxycarbonyl group or a lower alkoxycarbonyloxy-substituted lower alkyl group, wherein R ⁴ is as defined above.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as defined above.

(507) R¹Represents a hydrogen atom;^TwoIs hydrogen
Atom, phenyl group, morpholino-substituted lower alkyl group or
R represents an imidazolyl-substituted lower alkyl group;^ThreeIs a hydrogen source
, Lower alkyl group, lower alkanoyloxy-substituted lower
Alkyl group, lower alkoxycarbonyl group or lower alkyl group
A oxycarbonyloxy-substituted lower alkyl group;
^FourIs a group represented by the above [Chemical Formula 27]; substituted on the phenyl ring
A lower alkoxy group, a halogen atom, a substituent
Lower alkanoyl group and phenyl lower alkenyl car
Amide which may have a group selected from the group consisting of a bonyl group
Group, lower alkoxy group substituted lower alkoxy group, tetra
Having a lower alkyl group as a substituent on the sol ring
Tetrazolyl group, hydroxyl group, group -OA_Four-CO-
NR⁴⁰R⁴¹(A_FourRepresents a lower alkylene group. R⁴⁰as well as
R⁴¹Represents the same or different hydrogen atom or lower alkyl group
Show. Also R⁴⁰And R⁴¹Is the nitrogen atom to which they bind
With or through another nitrogen or oxygen atom
Form a 5- or 6-membered saturated heterocyclic ring
May be implemented. ), Lower alkenyloxy group, nitro group
And lower sometimes having a halogen atom as a substituent
Alkyl which may have a group selected from the group consisting of alkyl groups
Enyl lower alkenyl group; alkenyl group; cycloalkyl
Lower alkyl group; naphthyl lower alkyl group; phenyl
May have a lower alkoxy group as a substituent on the ring.
Phenylthio-substituted lower alkyl group; placed on the phenyl ring
Phenyl which may have a lower alkoxy group as a substituent
Rusulfinyl-substituted lower alkyl group; placed on phenyl ring
Phenyl which may have a lower alkoxy group as a substituent
Rusulfonyl-substituted lower alkyl group; phenoxy-substituted lower alkyl group
Alkyl group; group -A_Five-CR⁴²R⁴³R⁴⁴(Where A_FiveIs low
And a lower alkylene group. R ⁴²And R⁴³Are together
= O, group = N-OH or lower alkylenedioxy group
Shall be established. R⁴⁴Is a substituent on the phenyl ring
Indicates a phenyl group that may have a lower alkoxy group
You. ) Or on the 2,3-dihydro-1H-indenyl ring
An oxo group as a substituent, a hydroxyl group and a lower
Groups selected from the group consisting of silyloxy groups having an alkyl group
2,3-dihydro-1H-indenyl which may have
A lower alkyl group substituted with m, n and r are as defined above.
The same quinoxaline derivative represented by the general formula (1)
Or a salt thereof.

(508) R ¹ represents a hydrogen atom, R ² represents a hydrogen atom, a phenyl group, a morpholino-substituted lower alkyl group or an imidazolyl-substituted lower alkyl group, and R ³ represents a phenyl lower alkoxycarbonyl group; a lower alkanoyl group;
A lower alkoxy lower alkyl group; a phenoxycarbonyl group; a lower alkanoyl group-substituted lower alkyl group; a benzoyl-substituted lower alkyl group which may have a halogen atom as a substituent on a phenyl ring; a group -ER ⁵² R ⁵³ (R ⁵²
And R ⁵³ are the same or different and represent a hydrogen atom, a lower alkyl group, a lower alkoxycarbonyl group or a phenyl group. R ⁵² and R ⁵³ may be bonded to each other with or without another nitrogen atom or oxygen atom together with the nitrogen atom to which they are bonded to form a 5- or 6-membered saturated heterocyclic ring. E represents a lower alkylene group, a group -C (= O)-or a group -C (= O) -A- (A is a lower alkylene group). ) Or is a group represented by [Chemical Formula 26], wherein R ⁴ is a group represented by the above [Chemical Formula 27]; a lower alkoxy group as a substituent, a halogen atom, a lower alkanoyl group and a phenyl as a substituent on a phenyl ring. An amino group which may have a group selected from the group consisting of a lower alkenylcarbonyl group, a lower alkoxy group, a substituted lower alkoxy group, a tetrazolyl group which may have a lower alkyl group as a substituent on a tetrazole ring, a hydroxyl group, a group -O -A ₄ -CO-N
R ⁴⁰ R ⁴¹ (A ₄ represents a lower alkylene group .R ⁴⁰ and R
⁴¹ is the same or different and represents a hydrogen atom or a lower alkyl group. R ⁴⁰ and R ⁴¹ may be bonded to each other with or without another nitrogen atom or oxygen atom together with the nitrogen atom to which they are bonded to form a 5- or 6-membered saturated heterocyclic ring. ), A lower alkenyloxy group, a nitro group and a phenyl lower alkenyl group which may have a group selected from the group consisting of a lower alkyl group which may have a halogen atom as a substituent; an alkenyl group; a cycloalkyl lower alkyl group; A lower alkyl group; a phenylthio-substituted lower alkyl group which may have a lower alkoxy group as a substituent on the phenyl ring; a phenylsulfinyl-substituted lower alkyl group which may have a lower alkoxy group as a substituent on the phenyl ring; A phenylsulfonyl-substituted lower alkyl group which may have a lower alkoxy group as a substituent; a phenoxy-substituted lower alkyl group; a group represented by the above formula [28]; a group -A ₅ -C
R ⁴² R ⁴³ R ⁴⁴ (where A ₅ represents a lower alkylene group; R
⁴² and R ⁴³ are taken together to form a group = O, a group = N-OH or a lower alkylenedioxy group. R ⁴⁴ represents a phenyl group which may have a lower alkoxy group as a substituent on the phenyl ring. ); 2,3-dihydro-
A 2,3-dihydro-1H-indenyl-substituted lower alkyl group which may have on the 1H-indenyl ring a group selected from the group consisting of an oxo group, a hydroxyl group and a silyloxy group having a lower alkyl group as a substituent Or a quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as defined above.

(509) R ¹ represents a hydrogen atom, R ² represents a hydrogen atom, a phenyl group, a morpholino-substituted lower alkyl group or an imidazolyl-substituted lower alkyl group, and R ³ and R ⁴
Is a 1,2,3,4-tetrahydroisoquinolyl group formed by bonding together with the nitrogen atom to which they are bonded (this heterocyclic ring may have a lower alkoxy group as a substituent). , M, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(510) R ¹ represents a halogen atom, a lower alkyl group, a lower alkoxy group, an amino group which may have a lower alkyl group as a substituent or an aminocarbonyl group which may have a lower alkyl group as a substituent. , R
² represents a lower alkyl group which may have a halogen atom as a substituent, R ³ represents a hydrogen atom, a lower alkanoyloxy-substituted lower alkyl group, lower alkoxycarbonyl group or a lower alkoxycarbonyloxy-substituted lower alkyl group, R ⁴ Represents a group represented by the above [Chemical Formula 28] or a group represented by the above [Chemical Formula 34], and m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(511) R ¹ represents a halogen atom, a lower alkyl group, a lower alkoxy group, an amino group which may have a lower alkyl group as a substituent or an aminocarbonyl group which may have a lower alkyl group as a substituent. , R
² represents a lower alkyl group which may have a halogen atom as a substituent, R ³ represents a hydrogen atom, a lower alkyl group,
A lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group or a lower alkoxycarbonyloxy-substituted lower alkyl group, wherein R ⁴ is a group represented by the above formula; a lower alkoxy group or a halogen atom as a substituent on a phenyl ring; An amino group, which may have a group selected from the group consisting of a lower alkanoyl group and a phenyl lower alkenylcarbonyl group as a substituent, a lower alkoxy group, a substituted lower alkoxy group, and a tetrazole ring having a lower alkyl group as a substituent. there tetrazolyl group, a hydroxyl group, .R ⁴⁰ and R ⁴¹ groups ^{_{-O-a 4 -CO-NR 40}} R 41 (a 4 represents a lower alkylene group refers to the same or different and each represents a hydrogen atom or a lower alkyl group. the R ⁴⁰ and R ⁴¹ are the other nitrogen atom or oxygen atom together with the nitrogen atom to which they are attached May form a saturated 5- or 6-membered heterocyclic ring bonded to each other without or via.),
A phenyl lower alkenyl group which may have a group selected from the group consisting of a lower alkenyloxy group, a nitro group and a lower alkyl group which may have a halogen atom as a substituent; an alkenyl group; a cycloalkyl lower alkyl group;
Naphthyl lower alkyl group; phenylthio-substituted lower alkyl group which may have a lower alkoxy group as a substituent on a phenyl ring; phenylsulfinyl-substituted lower alkyl group which may have a lower alkoxy group as a substituent on a phenyl ring; A phenylsulfonyl-substituted lower alkyl group which may have a lower alkoxy group as a substituent thereon; a phenoxy-substituted lower alkyl group;
₅ -CR ⁴² R ⁴³ R ⁴⁴ (wherein A ₅ are a lower alkylene group .R ⁴² and R ⁴³ together group = O, group = N-OH
Alternatively, a lower alkylenedioxy group is formed.
R ⁴⁴ represents a phenyl group which may have a lower alkoxy group as a substituent on the phenyl ring. ) Or 2,3-dihydro- which may have on the 2,3-dihydro-1H-indenyl ring a group selected from the group consisting of an oxo group, a hydroxyl group and a silyloxy group having a lower alkyl group as a substituent. A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m represents a lower alkyl group substituted by a 1H-indenyl group, and r represents the same as above.

(512) R ¹ represents a halogen atom, a lower alkyl group, a lower alkoxy group, an amino group which may have a lower alkyl group as a substituent or an aminocarbonyl group which may have a lower alkyl group as a substituent. , R
² represents a lower alkyl group which may have a halogen atom as a substituent; R ³ represents a phenyl lower alkoxycarbonyl group; a lower alkanoyl group; a lower alkoxy lower alkyl group; a phenoxycarbonyl group; a lower alkanoyl group-substituted lower alkyl group; A benzoyl-substituted lower alkyl group which may have a halogen atom as a substituent on the ring; a group -ER ⁵² R ⁵³ (R ⁵² and R ⁵³ are the same or different and are a hydrogen atom, a lower alkyl group, a lower alkoxycarbonyl group; And R ⁵² and R ⁵³ are bonded together with or without another nitrogen atom or oxygen atom together with the nitrogen atom to which they are bonded to form a 5- or 6-membered saturated heterocyclic ring. E is a lower alkylene group, a group -C (= O)-or a group -C (= O) -A-
(A is a lower alkylene group). ) Or the form is
6], wherein R ⁴ is a group represented by the above formula [Chemical formula 27]; a lower alkoxy group as a substituent, a halogen atom, a lower alkanoyl group and a phenyl lower alkenylcarbonyl group as substituents on a phenyl ring. Amino group that may have a group selected from, lower alkoxy group substituted lower alkoxy group, tetrazolyl group that may have a lower alkyl group as a substituent on the tetrazole ring,
Hydroxyl, .R ⁴⁰ and R ⁴¹ groups ^{_{-O-A 4 -CO-NR 40}} R 41 (A 4 represents a lower alkylene group is a hydrogen atom or a lower alkyl group the same or different. The R ⁴⁰ and R ⁴¹
May be bonded to each other with or without another nitrogen atom or oxygen atom together with the nitrogen atom to which they are bonded to form a 5- or 6-membered saturated heterocyclic ring. ), A lower alkenyloxy group, a nitro group and a phenyl lower alkenyl group which may have a group selected from the group consisting of a lower alkyl group which may have a halogen atom as a substituent; an alkenyl group; a cycloalkyl lower alkyl group; A lower alkyl group; a phenylthio-substituted lower alkyl group which may have a lower alkoxy group as a substituent on the phenyl ring; a phenylsulfinyl-substituted lower alkyl group which may have a lower alkoxy group as a substituent on the phenyl ring; phenylsulfonyl-substituted lower alkyl group which may have a lower alkoxy group as a substituent; a phenoxy-substituted lower alkyl group; chemical formula 28] a group represented by; group _{^{-A 5 -CR 42 R 43 R 44}} ( wherein a ₅ .R ⁴² and R ⁴³ represents a lower alkylene group together based on Of O, as forming a group = N-OH or a lower alkylenedioxy group .R ⁴⁴ represents a phenyl group which may have a lower alkoxy group as a substituent on the phenyl ring);. 2,3-Dihydro 2,3-dihydro-1H-indenyl-substituted lower alkyl having a group selected from the group consisting of an oxo group, a hydroxyl group and a silyloxy group having a lower alkyl group as a substituent on a -1H-indenyl ring. A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m represents a group or a group represented by the above formula, and m, n, and r are the same as described above.

(513) R ¹ represents a halogen atom, a lower alkyl group, a lower alkoxy group, an amino group which may have a lower alkyl group as a substituent or an aminocarbonyl group which may have a lower alkyl group as a substituent. , R
² represents a lower alkyl group which may have a halogen atom as a substituent, and R ³ and R ⁴ are a 1,2,3,4-tetrahydroisoquinolyl group formed by bonding together with a nitrogen atom to which they are bonded. (Which may have a lower alkoxy group as a substituent on the heterocyclic ring), m,
n and r are the same as described above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(514) R ¹ represents a halogen atom, a lower alkyl group, a lower alkoxy group, an amino group which may have a lower alkyl group as a substituent or an aminocarbonyl group which may have a lower alkyl group as a substituent. , R
² is a hydrogen atom, a phenyl group, a morpholino-substituted lower alkyl group or an imidazolyl-substituted lower alkyl group, R ³
Represents a hydrogen atom, a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group or a lower alkoxycarbonyloxy-substituted lower alkyl group, and R ⁴ represents a group represented by the above [Chemical Formula 28] or a group represented by the above [Chemical Formula 34]. And m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(515) R ¹ represents a halogen atom, a lower alkyl group, a lower alkoxy group, an amino group which may have a lower alkyl group as a substituent or an aminocarbonyl group which may have a lower alkyl group as a substituent. , R
² is a hydrogen atom, a phenyl group, a morpholino-substituted lower alkyl group or an imidazolyl-substituted lower alkyl group, R ³
Represents a hydrogen atom, a lower alkyl group, a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group or a lower alkoxycarbonyloxy-substituted lower alkyl group, and R ⁴ is a group represented by the above [Chemical Formula 27]; A lower alkoxy group as a group, a halogen atom, an amino group which may have a group selected from the group consisting of a lower alkanoyl group and a phenyl lower alkenylcarbonyl group as a substituent, a lower alkoxy group, a substituted lower alkoxy group, and a substituent on the tetrazole ring A tetrazolyl group, a hydroxyl group, a group -OA which may have a lower alkyl group
_{^{4 -CO-NR 40 R 41 (}} A 4 is .R ⁴⁰ and R ⁴¹ represents a lower alkylene group represents a hydrogen atom or a lower alkyl group the same or different. The R ⁴⁰ and R ^41, the nitrogen to which they are attached And may be bonded to each other via an nitrogen atom or an oxygen atom together with or without an atom to form a 5- or 6-membered saturated heterocyclic ring.), A lower alkenyloxy group, a nitro group and a halogen atom as a substituent A phenyl lower alkenyl group which may have a group selected from the group consisting of a lower alkyl group which may have: an alkenyl group;
Cycloalkyl lower alkyl group; naphthyl lower alkyl group; phenylthio-substituted lower alkyl group which may have a lower alkoxy group as a substituent on a phenyl ring; phenylsulfinyl-substituted which may have a lower alkoxy group as a substituent on a phenyl ring. A lower alkyl group; a phenylsulfonyl-substituted lower alkyl group which may have a lower alkoxy group as a substituent on the phenyl ring; a phenoxy-substituted lower alkyl group; a group -A ₅ -CR ⁴² R ⁴³ R
⁴⁴ (wherein A ₅ represents a lower alkylene group; R ⁴² and R ⁴³
Together form a group = O, a group = N-OH or a lower alkylenedioxy group. R ⁴⁴ represents a phenyl group which may have a lower alkoxy group as a substituent on the phenyl ring. ) Or 2,3-dihydro- which may have on the 2,3-dihydro-1H-indenyl ring a group selected from the group consisting of an oxo group, a hydroxyl group and a silyloxy group having a lower alkyl group as a substituent.
Represents a 1H-indenyl-substituted lower alkyl group;
And r are the same as described above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(516) R ¹ represents a halogen atom, a lower alkyl group, a lower alkoxy group, an amino group which may have a lower alkyl group as a substituent or an aminocarbonyl group which may have a lower alkyl group as a substituent. , R
² is a hydrogen atom, a phenyl group, a morpholino-substituted lower alkyl group or an imidazolyl-substituted lower alkyl group, R ³
Is a phenyl lower alkoxycarbonyl group; a lower alkanoyl group; a lower alkoxy lower alkyl group; a phenoxycarbonyl group; a lower alkanoyl group-substituted lower alkyl group;
A benzoyl-substituted lower alkyl group which may have a halogen atom as a substituent on the phenyl ring; a group -ER ⁵² R
⁵³ (R ⁵² and R ⁵³ are the same or different and each represent a hydrogen atom, a lower alkyl group, a lower alkoxycarbonyl group or a phenyl group. R ⁵² and R ⁵³ represent, together with the nitrogen atom to which they are bonded, another nitrogen atom or oxygen E may be bonded to each other via an atom or without an atom to form a 5- or 6-membered saturated heterocyclic ring, wherein E is a lower alkylene group, a group -C (=
O)-or a group -C (= O) -A- (A is a lower alkylene group). ) Or is a group represented by [Chemical Formula 26], wherein R ⁴ is a group represented by the above [Chemical Formula 27]; a lower alkoxy group as a substituent, a halogen atom, a lower alkanoyl group and a phenyl as a substituent on a phenyl ring. An amino group which may have a group selected from the group consisting of a lower alkenylcarbonyl group, a lower alkoxy group-substituted lower alkoxy group,
Tetrazolyl group which may have a lower alkyl group as a substituent on the tetrazole ring, a hydroxyl group, a group -O-A ₄ -
^{CO-NR 40 R 41 (A} 4 represents a lower alkylene group .R
⁴⁰ and R ⁴¹ are the same or different and each represent a hydrogen atom or a lower alkyl group. R ⁴⁰ and R ⁴¹ may be bonded to each other with or without another nitrogen atom or oxygen atom together with the nitrogen atom to which they are bonded to form a 5- or 6-membered saturated heterocyclic ring. ), A lower alkenyloxy group, a nitro group and a phenyl lower alkenyl group which may have a group selected from the group consisting of a lower alkyl group which may have a halogen atom as a substituent; an alkenyl group; a cycloalkyl lower alkyl group; A lower alkyl group; a phenylthio-substituted lower alkyl group which may have a lower alkoxy group as a substituent on the phenyl ring; a phenylsulfinyl-substituted lower alkyl group which may have a lower alkoxy group as a substituent on the phenyl ring; A phenylsulfonyl-substituted lower alkyl group which may have a lower alkoxy group as a substituent; a phenoxy-substituted lower alkyl group; a group represented by the above [Chemical Formula 28];
A ₅ -CR ⁴² R ⁴³ R ⁴⁴ (where A ₅ represents a lower alkylene group; R ⁴² and R ⁴³ together form a group = O, a group = NO
H or a lower alkylenedioxy group is formed. R ⁴⁴ represents a phenyl group which may have a lower alkoxy group as a substituent on the phenyl ring. ); 2,3-
2,3-dihydro-1H-indenyl group-substituted lower having a group selected from the group consisting of an oxo group, a hydroxyl group and a silyloxy group having a lower alkyl group as a substituent on the dihydro-1H-indenyl ring. A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m represents an alkyl group or a group represented by the above formula, and m, n, and r are the same as those described above.

(517) R ¹ represents a halogen atom, a lower alkyl group, a lower alkoxy group, an amino group which may have a lower alkyl group as a substituent or an aminocarbonyl group which may have a lower alkyl group as a substituent. , R
² is a hydrogen atom, a phenyl group, a morpholino-substituted lower alkyl group or an imidazolyl-substituted lower alkyl group, R ³
And R ⁴ are a 1,2,3,4-tetrahydroisoquinolyl group formed by bonding together with the nitrogen atom to which they are bonded (this heterocyclic ring may have a lower alkoxy group as a substituent. And m, n and r are the same as defined above, and a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(518) In the group represented by the above formula [28], the saturated or unsaturated heterocyclic portion of the saturated or unsaturated heterocyclic-substituted lower alkyl group represented by the formula [29] is benzofuryl,
Benzothienyl, indolyl, 2,3-dihydrobenzofuryl, perhydrobenzofuryl, quinolyl, benzimidazolyl, benzothiazolyl, imidazo [1.2-
a] Pyridyl, 1,4-benzodioxanyl, furo [3.2-c] pyridyl, 1,2,3,4-tetrahydrofuro [2.3-g] quinolyl, furo [2.3-g] Quinolyl, 3,4-dihydrofuro [2.3-g] quinolyl, thiazolyl, pyridyl, furyl, imidazolyl,
(502), (504), (506), (508), (510), and (51) which are 1,2,3,4-tetrazolyl or oxazolyl groups.
2) A quinoxaline derivative represented by the general formula (1) described in (514) or (516) or a salt thereof.

(519) The saturated or unsaturated heterocyclic-substituted lower alkyl group represented by the formula [29] in the group represented by the formula [28], wherein the saturated or unsaturated heterocyclic portion is a benzofuryl or oxazolyl group. (502), (504), (506),
(508), (510), (512), (514) and a quinoxaline derivative represented by the general formula (1) described in (516) or a salt thereof.

(520) The saturated or unsaturated heterocyclic-substituted lower alkenyl group represented by [Formula 35] in the group represented by [Formula 34] is substituted with benzofuryl, benzothienyl, carbostyryl. , 3,4-dihydrocarbostyril, furo [3.2-c] pyridyl, 1,
2,3,4-tetrahydrofuro [2.3-g] quinolyl, furo [2.3-g] quinolyl, 3,4-dihydrofuro [2.3-g] quinolyl, naphtho [2.1-b] furyl Or an oxazolyl group (502), (504), (50
6) A quinoxaline derivative represented by the general formula (1) described in (508), (510), (512), (514) or (516) or a salt thereof.

(521) In the above-mentioned (502), the saturated or unsaturated heterocyclic moiety of the saturated or unsaturated heterocyclic-substituted lower alkenyl group represented by the formula [35] is a benzofuryl group. ), (504), (506), (508), (510)
, (512), (514) and (516). The quinoxaline derivative represented by the general formula (1) or a salt thereof.

(522) 2- [3- (Benzofuran-2-yl) -2-butenylaminocarbonyl] -3-methylquinoxaline-4-oxide, 2-[(3-methyl-7-
Trifluoromethylbenzofuran-2-yl) methylaminocarbonyl] -3-methylquinoxaline-4-oxide, 2-[(2-phenyl-5-methyloxazol-4-yl) methylaminocarbonyl] -3-methylquinoxaline- 4-oxide, 2-{[5- (2,5-dimethylthiazol-4-yl) benzofuran-3-yl] methylaminocarbonyl} -3-methylquinoxaline-4-oxide, 2- {3- [5- (2-methyl-
1,2,3,4-tetrazol-5-yl) benzofuran-2-yl] -2-butenylaminocarbonyl｝ -3
-Methylquinoxaline-4-oxide, 2- [5- (benzofuran-2-yl) -2,4-hexadienylaminocarbonyl] -3-methylquinoxaline-4-oxide, 2- {3- [5- ( 2,5-dimethylthiazole-
4-yl) benzofuran-2-yl] -2-butenylaminocarbonyl} -3-methylquinoxaline-4-oxide, 2- {3- [5- (thiazol-2-yl) benzofuran-2-yl]- 2-butenylaminocarbonyl {-3-methylquinoxaline-4-oxide, 2-
[3- (5,7-difluorobenzofuran-2-yl)
-2-butenylaminocarbonyl] -3-methylquinoxaline-4-oxide, 2- {N- [3- (benzofuran-2-yl) -2-butenyl] -N-methoxycarbonylaminocarbonyl} -3-methyl Quinoxaline-4
-Oxide, 2- {N- [3- (benzofuran-2-yl) -2-butenyl] -N-propanoyloxymethylaminocarbonyl} -3-methylquinoxaline-4-oxide, 2- {N- [3 -(Benzofuran-2-yl)
-2-butenyl] -N-acetyloxymethylaminocarbonyl} -3-methylquinoxaline-4-oxide,
2- {N- [3- (benzofuran-2-yl) -2-butenyl] -N-ethoxycarbonylaminocarbonyl}
-3-methylquinoxaline-4-oxide, 2- {N-
[(3-methyl-7-trifluoromethylbenzofuran-2-yl) methyl] -N-acetoxymethylaminocarbonyl} -3-methylquinoxaline-4-oxide and 2- {N-[(2-phenyl-5- Methyloxazol-4-yl) methyl] -N-acetoxymethylaminocarbonyl} -3-methylquinoxaline-4-oxide or a salt thereof.

In the compounds of the present invention, m and n are 1 at the same time.
, A compound in which m is 1 and n is 0, a compound in which m is 0 and n is 1 and a compound in which m and n are simultaneously 0, and a compound in which m is 1 and n is 0 is particularly preferable.

Examples of the heterocyclic group represented by the above formula include pyridyl, thiazolyl, furyl, benzimidazolyl, benzothiazolyl, oxazolyl, quinolyl,
Indolyl, 1,4-benzodioxanyl, 3,4-dihydrofuro [2.3-g] quinolyl, 1,2,3,4-
Tetrahydrofuro [2.3-g] quinolyl, furo [3.
2-c] pyridyl, furo [2.3-g] quinolyl, benzofuryl, benzothienyl, 2,3-dihydrobenzofuryl, perhydrobenzofuryl, imidazolyl, 1,
A 2,3,4-tetrazolyl, imidazo [1.2-a] pyridyl group and the like are particularly preferred.

As the heterocyclic group of the group represented by the above formula, 1,2,3,4-tetrazolyl, thiazolyl,
Pyridyl, oxazolyl, 1,2,3,5-oxathiadiazolyl, 1,3,4-triazolyl, 1,2,4-
Oxadiazolyl, 1,2,4-triazinyl, imidazolyl, 1,3,4-oxadiazolyl, pyrimidinyl, 1,2,3,4-tetrazolyl group and the like are particularly preferable.

Examples of the heterocyclic group represented by the above formula include thiazolyl, 1,2,3,4-tetrazolyl,
A thiazolidinyl group and the like are particularly preferred.

Examples of the heterocyclic group represented by the above formula include benzofuryl, benzothiazolyl, carbostyryl, 3,4-dihydrocarbostyril, furo [3.2
-C] pyridyl, benzothienyl, naphtho [2.1-
b] Furyl, oxazolyl, furo [2.3-g] quinolyl, 3,4-dihydrofuro [2.3-g] quinolyl group and the like are particularly preferred.

The compound of the present invention represented by the above general formula (1) can be produced by various methods, and a preferred example thereof is produced by the following method.

[0641]

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[Wherein R ¹ , R ² , R ³ , R ⁴ , r, m and n are as defined above. The reaction between the compound (2) and the compound (3) is carried out according to a usual amide bond formation reaction. The amide bond formation reaction is carried out by various known methods, for example, (a) the mixed acid anhydride method, for example, by reacting a carboxylic acid (2) with a halocarboxylic acid alkyl ester to form a mixed acid anhydride, and adding the amine (3)
(B) active ester method, for example, converting carboxylic acid (2) into an active ester such as p-nitrophenyl ester, N-hydroxysuccinimide ester, 1-hydroxybenzotriazole ester and the like, and adding amine (3 (C) a carbodiimide method; that is, a method in which an amine (3) is condensed with a carboxylic acid (2) in the presence of an activator such as dicyclohexylcarbodiimide, carbonyldiimidazole, or the like; A method of reacting carboxylic acid (2) with a dehydrating agent such as acetic anhydride to form carboxylic anhydride and reacting with amine (3), and reacting amine (3) with an ester of carboxylic acid (2) and lower alcohol. Method: reacting an amine (3) with an acid halide of a carboxylic acid (2), that is, a carboxylic acid halide. It can be carried out by law or the like. Further, a method in which carboxylic acid (2) is activated with a phosphorus compound such as triphenylphosphine or diethylchlorophosphate and reacted with amine (3), and carboxylic acid (2) is further reacted with phosgene or trichloromethyl chloroformate or the like. After forming an N-carboxyamino acid anhydride, a method of reacting the anhydride with an amine (3) may be used. Further, a method of activating the carboxylic acid (2) with an acetylene compound such as trimethylsilylethoxyacetylene and reacting the activated carboxylic acid with the amine (3) can be used.

In the mixed acid anhydride method shown in the above (A), the mixed acid anhydride used is obtained by a usual Jotten-Baumann reaction, and this is usually reacted with the amine (3) without isolation. Yields a compound of the general formula (1). The Schotten-Baumann reaction is performed in the presence of a basic compound. As the basic compound to be used, a compound commonly used in the Schotten-Baumann reaction is used. For example, triethylamine, trimethylamine, pyridine, dimethylaniline, N-methylmorpholine, 4-dimethylaminopyridine, 1,5-diazabicyclo [4.3 .0] nonene-5 (DBN), 1,8-diazabicyclo [5.4.0] undecene-7 (DB
U), organic bases such as 1,4-diazabicyclo [2.2.2] octane (DABCO), and inorganic bases such as potassium carbonate, sodium carbonate, potassium hydrogencarbonate and sodium hydrogencarbonate. The reaction is about -20 to 100
C., preferably at 0-50 C. for about 5 minutes to 10 hours,
Preferably, the reaction is performed for about 5 minutes to 2 hours. The reaction between the resulting mixed acid anhydride and the amine (3) is about -20 to 15
The reaction is carried out at 0 ° C., preferably 10 to 50 ° C., for about 5 minutes to 10 hours, preferably about 5 minutes to 5 hours. In addition, the mixed acid anhydride is generally a solvent commonly used in this kind of mixed acid anhydride method, specifically, halogenated hydrocarbons such as methylene chloride, chloroform, dichloroethane, and aromatic hydrocarbons such as benzene, toluene, and xylene. , Diethyl ether, dioxane, diisopropyl ether,
Ethers such as tetrahydrofuran and dimethoxyethane; esters such as methyl acetate and ethyl acetate;
The reaction is carried out in a suitable solvent or a mixed solvent such as an aprotic polar solvent such as 3,3-tetramethylurea, N, N-dimethylformamide, dimethylsulfoxide and hexamethylphosphoric triamide, or in the absence thereof. Examples of the alkyl halocarboxylate used in the production of the mixed acid anhydride include methyl chloroformate, methyl bromoformate, ethyl chloroformate, ethyl bromoformate, and isobutyl chloroformate. The halocarboxylic acid alkyl ester is generally used in an amount at least equimolar to the amine (3), preferably about 1 to 1.5 moles. The amount of the amine (3) used is usually at least equimolar to the carboxylic acid (2), preferably about 1 to 1.5 moles.

In the active ester method shown in (b) above, for example, in the case of using N-hydroxysuccinimide ester, the presence or absence of a basic compound in a suitable solvent which does not affect the reaction is taken as an example. Done down. Further, a condensing agent such as dicyclohexylcarbodiimide, carbonyldiimidazole, 1-ethyl-3- (3'-dimethylaminopropyl) carbodiimide may be added to the reaction system of the reaction. Here, as the basic compound, any of the basic compounds used in the Schotten-Baumann reaction can be used, and in addition to them, sodium acetate,
Sodium benzoate, sodium formate, potassium acetate,
Alkali metal carboxylate such as lithium benzoate and cesium acetate, and alkali metal halide such as potassium fluoride and cesium fluoride can also be used. As the solvent, specifically, methylene chloride, chloroform, halogenated hydrocarbons such as dichloroethane, benzene, toluene, aromatic hydrocarbons such as xylene, diethyl ether, dioxane, tetrahydrofuran, ethers such as dimethoxyethane, Esters such as methyl acetate and ethyl acetate; aprotic polar solvents such as N, N-dimethylformamide, dimethyl sulfoxide and hexamethylphosphoric triamide; and mixed solvents thereof. The reaction is usually performed at 0 to 150 ° C, preferably 10 to 100 ° C.
And ends in 5 to 30 hours. The use ratio of the amine (3) and the N-hydroxysuccinimide ester is usually at least equimolar, preferably equimolar to 2 times mol with respect to the compound (2).

The amine (3) and the carboxylic acid (2) can be converted to triphenylphosphine, triphenylphosphine-2,2'-dipyridyldisulfide, diethylchlorophosphate, diphenylphosphinyl chloride, phenyl N-phenylphosphoramide Compound (1) can also be obtained by reacting in the presence of a condensing agent for a phosphorus compound such as chloridate, diethyl cyanophosphate, bis (2-oxo-3-oxazolidinyl) phosphinic chloride. As the basic compound used here, known compounds can be widely used, and examples thereof include sodium hydroxide and potassium hydroxide in addition to the basic compound used in the Schotten-Baumann reaction. Examples of the solvent include, in addition to the solvent used in the mixed acid anhydride method, pyridine, acetone, acetonitrile, etc., or a mixed solvent of two or more of the above solvents. The reaction is generally carried out at about -20 to 150 ° C, preferably at about 0 to 100 ° C, and is generally completed in 5 minutes to 30 hours. The amounts of the condensing agent and the amine (3) to be used are each at least about equimolar, preferably about equimolar to about 2 times the molar amount of the carboxylic acid (2).

Compound (1) can also be obtained by reacting amine (3) with carboxylic acid (2) in the presence of a condensing agent. The reaction is carried out in a suitable solvent,
It is performed in the presence or absence of a catalyst. The solvents used here include dichloromethane, dichloroethane,
Halogenated hydrocarbons such as chloroform and carbon tetrachloride,
Examples thereof include acetonitrile and dimethylformamide. Examples of the catalyst used include organic bases such as dimethylaminopyridine and 4-piperidinopyridine, salts such as pyridinium tosylate, camphorsulfonic acid, and mercury oxide. Examples of the condensing agent include acetylene compounds such as trimethylsilylethoxyacetylene. The condensing agent is usually equimolar to 1 to 1 with respect to the amine (3).
It is good to use 0 times molar amount, preferably 2 to 6 times molar amount. The carboxylic acid (2) is usually used in an amount of at least about 1 mole, preferably about 1 to 2 moles, per mole of the amine (3). The reaction is usually carried out at about 0 to 150 ° C., preferably at about room temperature to about 100 ° C., and is completed in about 1 to 10 hours.

In the case where the method of reacting the amine (3) with the carboxylic acid halide shown in the above (d) is employed, the reaction is carried out in a suitable solvent in the presence of a dehydrohalogenating agent. Usual basic compounds are used as the dehydrohalogenating agent. As the basic compound, known compounds can be widely used, and examples thereof include sodium hydroxide, potassium hydroxide, sodium hydride, potassium hydride and the like in addition to the basic compound used in the Schotten-Baumann reaction. As the solvent, in addition to the solvent used in the mixed acid anhydride method, for example, alcohols such as methanol, ethanol, propanol, butanol, 3-methoxy-1-butanol, ethyl cellosolve, methyl cellosolve, pyridine, acetone, acetonitrile or the above Examples thereof include a mixed solvent of two or more solvents. The ratio of the carboxylic acid halide to the amine (3) is not particularly limited and may be appropriately selected within a wide range. Usually, the amount of the latter is at least about equimolar to the former, preferably about 5 to 5 mol.
It is preferable to use about twice the molar amount. The reaction is usually carried out at -20 to
Carried out at about 180 ° C, preferably at about 0 to 150 ° C,
Generally, the reaction is completed in about 5 minutes to 30 hours.

In the above, the carboxylic acid halide is produced, for example, by reacting the carboxylic acid (2) with a halogenating agent without a solvent or in the presence of a solvent. As the solvent, any solvent can be used as long as it does not adversely affect the reaction. Examples thereof include aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as chloroform, methylene chloride and carbon tetrachloride, dioxane, and tetrahydrofuran. And ethers such as diethyl ether, dimethylformamide, dimethylsulfoxide and the like. As the halogenating agent, a usual halogenating agent that changes the hydroxyl group of the carboxy group to halogen can be used, and examples thereof include thionyl chloride, phosphorus oxychloride, phosphorus oxybromide, phosphorus pentachloride, and phosphorus pentabromide. . The ratio of the carboxylic acid (2) and the halogenating agent to be used is not particularly limited and may be appropriately selected. However, when the reaction is carried out in the absence of a solvent, the latter is usually used in a large excess with respect to the former, and When performing the reaction, the latter is usually at least about equimolar to the former,
Preferably, a 2- to 4-fold molar amount is used. The reaction temperature and the reaction time are not particularly limited either, but the reaction is usually carried out at room temperature to about 100 ° C, preferably at 50 to 80 ° C, for about 30 minutes to 6 hours.

In the case of employing the method of reacting the above-mentioned ester of carboxylic acid (2) with lower alcohol with amine (3), the reaction is carried out in a suitable solvent or without solvent. As the solvent used herein, any of the solvents used in the reaction between the carboxylic acid halide and the amine can be used. The amine (3) is usually used at least in an equimolar amount, preferably in an equimolar to 15-fold molar amount, based on the ester of the carboxylic acid (2) and the lower alcohol. The reaction is completed usually at room temperature to 150 ° C., preferably at room temperature to about 120 ° C., for about 1 to 20 hours.

[0650]

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[Wherein R ¹ , R ² , r, m and n are the same as above. X represents a halogen atom. R ^3a is a hydrogen atom, lower alkyl group, phenyl lower alkoxycarbonyl group, lower alkanoyloxy-substituted lower alkyl group, lower alkanoyl group, lower alkoxycarbonyl group, lower alkoxy lower alkyl group, phenoxycarbonyl group, lower alkanoyl group-substituted lower alkyl group A lower alkoxycarbonyloxy-substituted lower alkyl group, a benzoyl-substituted lower alkyl group which may have a halogen atom as a substituent on the phenyl ring, a group -ER ⁵² R ⁵³ (R ⁵² and R ⁵³ are
The same or different represents a hydrogen atom, a lower alkyl group, a lower alkoxycarbonyl group or a phenyl group. R ⁵² and R
⁵³ may be bonded to each other via or not via another nitrogen atom or oxygen atom together with the nitrogen atom to which they are bonded, to form a 5- or 6-membered saturated heterocyclic ring. E is a lower alkylene group, a group -C (= O)-or a group -C (=
O) -A- (A is a lower alkylene group). ), A group represented by the above [Chemical Formula 26], a group represented by the above [Chemical Formula 27], a lower alkoxy group as a substituent on a phenyl ring, a halogen atom, a lower alkanoyl group and a phenyl lower alkenylcarbonyl group as a substituent. amino group which may have a more selected group, a lower alkoxy-substituted lower alkoxy group, a tetrazolyl group which may have a lower alkyl group as a substituent on the tetrazole ring, a hydroxyl group, a group -O-a ₄ -CO- NR ⁴⁰ R ⁴¹ (A ₄ , R ⁴⁰ and R ⁴¹ are as defined above), a lower alkenyloxy group, a nitro group and a group selected from the group consisting of a lower alkyl group which may have a halogen atom as a substituent. Phenyl lower alkenyl, alkenyl, cycloalkyl lower alkyl, naphthyl lower alkyl, phenyl A phenylthio-substituted lower alkyl group which may have a lower alkoxy group as a substituent, a phenylsulfinyl-substituted lower alkyl group which may have a lower alkoxy group as a substituent on a phenyl ring, a lower alkoxy group as a substituent on a phenyl ring. A phenylsulfonyl-substituted lower alkyl group, a phenoxy-substituted lower alkyl group, a group represented by the above [Chemical Formula 28], a group -A
₅ -CR ⁴² R ⁴³ R ⁴⁴ (wherein A _5, R ^42, R ⁴³ and R ⁴⁴ are as defined above.), An oxo group as a substituent on the 2,3-dihydro -1H- indenyl ring, a hydroxyl group and a substituted It represents a 2,3-dihydro-1H-indenyl-substituted lower alkyl group which may have a group selected from the group consisting of a silyloxy group having a lower alkyl group or a group represented by the above formula. R ^3b represents R ^3a other than a hydrogen atom. R ^3c and R ^3d each represent a hydrogen atom or a lower alkyl group. The reaction of the compound of the general formula (1a) with the compound of the general formula (4a) is generally performed in a suitable inert solvent in the presence or absence of a basic compound. As the inert solvent used, for example, benzene, toluene, aromatic hydrocarbons such as xylene, tetrahydrofuran, dioxane, ethers such as diethylene glycol dimethyl ether,
Examples thereof include lower alcohols such as methanol, ethanol, isopropanol and butanol, ethyl acetate, acetone, acetonitrile, dimethyl sulfoxide, dimethylformamide, hexamethylphosphoric triamide and the like, and a mixed solvent thereof. Examples of the basic compound include sodium carbonate, potassium carbonate, sodium hydrogen carbonate, carbonates such as potassium hydrogen carbonate, sodium hydroxide, metal hydroxides such as potassium hydroxide, sodium hydride, potassium, sodium, sodium amide, and the like. Metal alcoholates such as sodium methylate and sodium ethylate, pyridine, N-ethyldiisopropylamine, dimethylaminopyridine, triethylamine, DB
Organic bases such as N, DBU and DABCO can be exemplified. The ratio of the compound of the general formula (1a) to the compound of the general formula (4a) is not particularly limited, and may be appropriately selected in a wide range. It is preferable to use an equimolar to about 10-fold molar amount. The reaction is usually carried out at about 0 to 200 ° C, preferably about 0 to 170 ° C, and generally for 30 minutes to 3 minutes.
The reaction is completed in about 0 hours. An alkali metal halide such as sodium iodide and potassium iodide may be added to the reaction system. Ammonium halides such as tetra-n-butylammonium iodide, tetra-n-butylammonium bromide, n-butyl-triethylammonium iodide, tetraethylammonium iodide, and tri-n-butylmethylammonium iodide; May be added.

The reaction of compound (1a) with compound (4b) is carried out without a solvent or in a suitable solvent in the presence of a reducing agent. Examples of the solvent used herein include water, alcohols such as methanol, ethanol, and isopropanol; acetonitrile, formic acid, acetic acid, dioxane, diethyl ether, diglyme, and ethers such as tetrahydrofuran; and aromatic hydrocarbons such as benzene, toluene, and xylene. Examples thereof include hydrogens or a mixed solvent thereof. As the reducing agent, for example, formic acid, alkali metal salts of fatty acids such as sodium formate, hydrogenating reducing agents such as sodium borohydride, sodium cyanoborohydride, lithium aluminum hydride, palladium-black, palladium-carbon, platinum oxide, platinum Examples thereof include catalytic reducing agents such as black and Raney nickel.

In the case of using formic acid as a reducing agent, the reaction temperature is usually from room temperature to about 200 ° C., preferably from 50 to 150 ° C.
C. is appropriate, and the reaction is completed in about 1 to 10 hours. The amount of formic acid used is preferably a large excess with respect to compound (1a).

In the case of using a hydride reducing agent, the reaction temperature is usually about -30 to 100 ° C, preferably 0 to 70 ° C.
The reaction is appropriately performed, and the reaction is completed in about 30 minutes to 15 hours. The amount of the reducing agent to be used is generally about equimolar to about 20-fold molar quantity, preferably about 1- to 6-fold molar quantity, relative to compound (1a). In particular, when lithium aluminum hydride is used as the reducing agent, it is preferable to use ethers such as diethyl ether, dioxane, tetrahydrofuran, and diglyme as solvents, and aromatic hydrocarbons such as benzene, toluene, and xylene.

When a catalytic reducing agent is further used, it is usually in a hydrogen atmosphere at normal pressure to about 20 atm, preferably normal pressure to about 10 atm, or a hydrogen donor such as formic acid, ammonium formate, cyclohexene, hydrazine hydrate and the like. The reaction is usually carried out at a temperature of about -30 to 100 ° C., preferably about 0 to 60 ° C., and the reaction is usually completed in about 1 to 12 hours. The amount of the catalytic reducing agent used may be the compound (1
0.1 to 40% by weight, preferably 1 to 40% by weight based on a)
The content is preferably about 20% by weight.

The amount of compound (4b) to be used is generally at least equimolar, preferably equimolar to large excess with respect to compound (1a).

[0657]

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[Wherein R ¹ , R ² , R ³ , R ⁴ , r, m and n are as defined above. The reaction for converting the compound (1c) to the compound (1d) and the reaction for converting the compound (1e) to the compound (1f) are both carried out in a suitable solvent in the presence of an oxidizing agent. Examples of the solvent used here include water, organic acids such as formic acid, acetic acid, and trifluoroacetic acid; alcohols such as methanol and ethanol; halogenated hydrocarbons such as chloroform and dichloromethane; and mixed solvents thereof. it can. As the oxidizing agent used, for example, formic acid, peracetic acid, pertrifluoroacetic acid, perbenzoic acid, m-chloroperbenzoic acid, o-
Peracids such as carboxyperbenzoic acid, hydrogen peroxide, sodium metaperiodate, dichromic acid, sodium dichromate,
Dichromates such as potassium dichromate, permanganate,
Examples include permanganates such as potassium permanganate and sodium permanganate, and lead salts such as lead tetraacetate. The oxidizing agent is usually used in an amount of at least equimolar, preferably equimolar to twice molar amount to the starting material. The above reaction is carried out usually at -10 to 40C, preferably at -10C to room temperature, and is completed in about 1 to 100 hours.

[0659]

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[Wherein R ¹ , R ² , R ^3a , R ⁸ , the group represented by the above formula, r, m, n, X and l are the same as described above. R ^9a is a hydrogen atom, a lower alkanoyl group, a lower alkyl group, a morpholinocarbonyl lower alkyl group, a cycloalkylcarbonyl group, a phenyl lower alkenylcarbonyl group, a lower alkylsulfonyl group, an aminocarbonyl group which may have a lower alkyl group as a substituent A phenylsulfonyl group, which may have a lower alkyl group as a substituent on the phenyl ring, a phenyl lower alkenyl group, a halogen atom, a lower alkoxy group as a substituent on the phenyl ring, and a lower alkanoyl group as a substituent. A benzoyl group which may have 1 to 3 groups selected from the group consisting of an amino group and a hydroxyl group, an amino group-substituted lower alkanoyl group which may have a lower alkanoyl group as a substituent, and a lower alkyl group which has a substituent Amino group A sulfonyl group, a phenyl-lower alkyl group, an amino group which may have a lower alkanoyl group as a phenyl group or a substituted group. R ^10a is a lower alkanoyl group, a cycloalkylcarbonyl group, a phenyl lower alkenylcarbonyl group, a halogen atom as a substituent on a phenyl ring, a lower alkoxy group, an amino group or a hydroxyl group which may have a lower alkanoyl group as a substituent. A benzoyl group which may have 1 to 3 selected groups or an amino-substituted lower alkanoyl group which may have a lower alkanoyl group as a substituent. R ^10b is a lower alkyl group, a morpholinocarbonyl lower alkyl group, a lower alkylsulfonyl group, an aminocarbonyl group which may have a lower alkyl group as a substituent, or a phenylsulfonyl which may have a lower alkyl group as a substituent on a phenyl ring. Group, a phenyl lower alkenyl group, an amino-substituted sulfonyl group or a phenyl lower alkyl group which may have a lower alkyl group as a substituent. q 'represents 1 or 2. R ^10c and R ^10d
Represents a hydrogen atom or a lower alkyl group, respectively. The reaction between the compound (1 g) and the compound (5) is carried out under the same conditions as in the reaction between the compound (2) and the compound (3) in the aforementioned Reaction Formula-1.

In the compound (1h), R ^10a is a lower alkanoyl group represented by the general formula (R ¹¹ ) ₂ O (7) or the general formula R ¹¹ X (8) [wherein R ¹¹ is a lower alkanoyl group] Represents a group. X is the same as above. The lower alkanoylation of the compound (1 g) using the compound represented by the formula (1) is also possible. This lower alkanoylation reaction is performed in the presence or absence of a basic compound.
Examples of the basic compound used include alkali metals such as sodium metal and potassium metal and hydroxides, carbonates, bicarbonates of these alkali metals, or organic bases such as N, N-dimethylaminopyridine, pyridine and piperidine. And the like. The reaction proceeds both without solvent and in a solvent. Examples of the solvent include ketones such as acetone and methyl ethyl ketone, ethers such as diethyl ether and dioxane, aromatic hydrocarbons such as benzene, toluene and xylene, water, pyridine and the like. The compound (7) or (8) is used in at least about an equimolar amount to the starting compound, but it is generally preferable to use an equimolar amount to a large excess amount.
Although the reaction proceeds at 00 ° C., it is generally preferable to carry out the reaction at about 0 to 150 ° C. The reaction time of the reaction is generally from 5 minutes to 5 minutes.
About a day.

The reaction of the compound (1g) with the compound (6a) or the compound (6b) is carried out under the same conditions as in the reaction of the compound (1a) with the compound (4a) or the compound (4b) in the aforementioned Reaction Formula-2. It is performed.

[0663]

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[Wherein R ¹ , R ² , R ⁸ , R ^3a , m, n,
q ′, R ⁹ , R ¹⁰ , r and the group represented by the above [Formula 29] are the same as described above. R ¹² represents a lower alkyl group. The hydrolysis reaction of compound (1j) can be carried out in a suitable solvent or without a solvent, in the presence of an acid or a basic compound. As the solvent used, for example, water, methanol, ethanol, lower alcohols such as isopropanol, acetone, ketones such as methyl ethyl ketone, dioxane, tetrahydrofuran, ethers such as ethylene glycol dimethyl ether, acetic acid, fatty acids such as formic acid, dimethylformamide, These mixed solvents can be exemplified. Examples of the acid include mineral acids such as hydrochloric acid, sulfuric acid and hydrobromic acid, and organic acids such as formic acid, acetic acid and aromatic sulfonic acid.Examples of the basic compound include sodium carbonate and potassium carbonate. Examples thereof include metal salts and metal hydroxides such as sodium hydroxide, potassium hydroxide and calcium hydroxide. The reaction proceeds usually at room temperature to about 200 ° C., preferably at room temperature to about 150 ° C., and is generally completed in about 10 minutes to 25 hours.

The reaction of the compound (1k) with the compound (9) is carried out under the same conditions as in the reaction of the compound (2) with the compound (3) in the aforementioned Reaction Formula-1.

[0666]

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[Wherein R ¹ , R ² , R ^3a , R ⁸ , m, n,
q ′, X, and the group represented by the above formula [29] are the same as described above. R ¹³ is a lower alkyl group, a phenyl lower alkyl group which may have an amino group which may have a lower alkanoyl group as a substituent on the phenyl ring, a carboxy-substituted lower alkyl group, a lower alkoxycarbonyl-substituted lower alkyl group, a lower alkoxy group It represents a substituted lower alkyl group, a lower alkenyl group, a lower alkanoyl group or a morpholinocarbonyl lower alkyl group. R ¹⁴ represents a lower alkoxy group, a phenyl lower alkoxy group which may have an amino group which may have a lower alkanoyl group as a substituent on the phenyl ring, a lower alkanoyloxy group or a lower alkoxy-substituted lower alkoxy group. In the reaction for converting the compound (1o) to the compound (1m), when R ¹⁴ is a phenyl lower alkoxy group, the compound (1o)
m) by reduction. This reduction reaction can be performed, for example, by catalytic hydrogenation in the presence of a catalyst in a suitable solvent. Examples of the dissolution used include water, acetic acid, alcohols such as methanol, ethanol and isopropanol, hydrocarbons such as hexane and cyclohexane, ethers such as dioxane, tetrahydrofuran, diethyl ether and ethylene glycol dimethyl ether, ethyl acetate and acetic acid. Examples thereof include esters such as methyl, aprotic polar solvents such as dimethylformamide, and a mixed solvent thereof. As the catalyst used, for example, palladium, palladium-
Black, palladium-carbon, platinum, platinum oxide, copper chromite, Raney nickel and the like. The amount of catalyst used is
In general, the amount is preferably about 0.02 to 1 times the amount of the compound (7). The reaction temperature is usually around -20 to 100 ° C,
Preferably, the pressure is about 0 to 80 ° C., and the hydrogen pressure is usually 1 to 10 atm. The reaction is generally completed in about 0.5 to 20 hours.

When R ¹⁴ is a lower alkoxy group or a lower alkoxy-substituted lower alkoxy group, the compound (1)
The reaction for converting o) to the compound (1m) is carried out by hydrolyzing the compound (1o). The hydrolysis is carried out in a suitable solvent in the presence of an acid. Examples of the solvent include water, lower alcohols such as methanol, ethanol, and isopropanol; ethers such as dioxane and tetrahydrofuran; halogenated hydrocarbons such as dichloromethane, chloroform and carbon tetrachloride; polar solvents such as acetonitrile; and mixtures thereof. Solvents and the like can be mentioned.
Examples of the acid include mineral acids such as hydrochloric acid, sulfuric acid and hydrobromic acid, fatty acids such as formic acid and acetic acid, Lewis acids such as boron trifluoride, aluminum chloride and boron tribromide, sodium iodide, potassium iodide and the like. And a mixture of the above-mentioned Lewis acid and iodide. The reaction is usually performed at 0 to 150 ° C,
It preferably proceeds at room temperature to 100 ° C.
It ends in about 5 to 50 hours.

When R ¹⁴ is a lower alkanoyloxy group, the reaction for converting the compound (1o) to the compound (1m) is carried out under the same reaction conditions as in the hydrolysis of the compound (1j) in the aforementioned reaction formula-5. You can go to.

The reaction of the compound (1m) with the compound (10) is carried out under the same conditions as in the reaction of the compound (1g) with the compound (6) in the aforementioned reaction formula-4. Compound (1n) in which R ¹³ is a lower alkanoyl group is compound (1n)
m) and the compound (7) can also be produced by reacting the compound (1g) and the compound (7) in the above reaction formula-4 under the same reaction conditions as the reaction.

[0671]

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[Wherein R ¹ , R ² , R ^3a , R ⁵ , R ⁸ ,
m, n, q ', A, X, r and the group represented by the above [Formula 29] are the same as described above. p 'represents 1 or 2. The halogenation reaction of compound (1p) or compound (1E) is performed in the presence of a usual halogenating agent. As the halogenating agent used in such a reaction, known ones can be widely used, and examples thereof include halogen molecules such as bromine and chlorine, and N such as iodine monochloride, sulfuryl chloride, N-bromosuccinimide, and N-chlorosuccinimide. Halogenating agents such as halogenosuccinimide;
The amount of the halogenating agent to be used is generally at least equimolar, preferably equimolar to 1.5-fold molar with respect to compound (1p) or compound (1E). Examples of the solvent used in the reaction include halogenated hydrocarbons such as dichloromethane, dichloroethane, chloroform, carbon tetrachloride, acetic acid, propionic acid, water, and a mixed solvent thereof. In the reaction, the reaction temperature is usually 0 ° C.
The reaction solvent has a boiling point of preferably 0 to 100 ° C., and the reaction is usually completed in about 1 to 10 hours.

[0673]

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[Wherein R ¹ , R ² , R ^3a , R ⁸ , m, n,
q ', X, r and the group represented by the above [Formula 29] are the same as described above. R ¹⁵ represents a lower alkyl group having a hydroxyl group as a substituent. R ¹⁶ represents a lower alkanoyl group. R ¹⁷ and R ¹⁸ each represent a lower alkyl group. R ¹⁹ represents a lower alkanoyloxy-substituted lower alkyl group. R ^18a represents a hydrogen atom or a lower alkyl group. R ^18c represents a phenyl group. R ^18b represents a lower alkyl group. The reaction for converting the compound (1r) to the compound (1s) is performed in a suitable solvent in the presence of an oxidizing agent. Examples of the oxidizing agent used herein include pyridinium chlorochromate, pyridinium chromate such as pyridinium dichlorochromate, dimethyl sulfoxide-oxalyl chloride, manganese dioxide, DDQ, dichromic acid, sodium dichromate, and dichromate. Examples thereof include dichromates such as potassium, and permanganates such as permanganate, potassium permanganate, and sodium permanganate. As the solvent used, for example, water, formic acid, acetic acid, organic acids such as trifluoroacetic acid, methanol, alcohols such as ethanol,
Examples thereof include halogenated hydrocarbons such as chloroform and dichloromethane, ethers such as tetrahydrofuran, diethyl ether and dioxane, dimethyl sulfoxide, dimethylformamide, and a mixed solvent thereof. The oxidizing agent is usually used in an amount of at least equimolar, preferably equimolar to 30-fold molar amount, based on the starting material. The reaction is usually completed at about 0 to 150 ° C, preferably about 0 to 100 ° C, for about 1 to 10 hours.

The reaction for converting compound (1r) to compound (1s) is carried out by reacting compound (1r) with an oxidizing agent in a suitable solvent in the presence of a co-oxidizing agent. As the solvent used in the reaction with the oxidizing agent, for example, pyridine, dioxane, tetrahydrofuran, ethers such as diethyl ether, benzene, toluene, aromatic hydrocarbons such as xylene, dichloromethane, dichloroethane, chloroform, carbon tetrachloride and the like Examples thereof include halogenated hydrocarbons, esters such as ethyl acetate, water, alcohols such as methanol, ethanol, isopropanol and t-butanol, and mixed solvents thereof. As the co-oxidizing agent used, for example, pyridine N-oxide, N
Organic amines N such as -ethyldiisopropylamine N-oxide, N-methylmorpholine N-oxide, trimethylamine N-oxide and triethylamine N-oxide
-Oxides and the like. Examples of the oxidizing agent include, for example, tetra-n-propylammonium pearl thenate. The amount of the co-oxidizing agent used is usually at least equimolar, preferably equimolar to
The molar amount is preferably 5 times. The amount of the oxidizing agent used is preferably a catalytic amount. The reaction is carried out at -20 to 150 ° C, preferably 0 to 100 ° C, and is generally completed in about 1 to 20 hours. The reaction proceeds advantageously when molecular sieves are added to the reaction system.

For the reaction for converting the compound (1s) to the compound (1r), a reduction method using a hydrogenating reducing agent is suitably used. Examples of the hydride reducing agent to be used include lithium aluminum hydride, diborane, diisobutylaluminum hydride, sodium borohydride, lithium borohydride, tetrabutylammonium borohydride, calcium borohydride, aluminum hydride and the like. ,
The amount used is at least 0.1 times, preferably 0.1 to 15 times the mol of the starting compound. This reduction reaction is usually carried out in a suitable solvent such as water, methanol,
Lower alcohols such as ethanol and isopropanol,
Using ethers such as tetrahydrofuran, diethyl ether, diisopropyl ether and diglyme, aromatic hydrocarbons such as benzene, toluene and xylene and a mixed solvent thereof, usually about -60 to 150 ° C, preferably-
The reaction is performed at 30 to 100 ° C. for about 10 minutes to 20 hours.

The reaction between compound (1s) and compound (11) is carried out in a suitable solvent. As the solvent used herein, any solvent can be used as long as it is a solvent used in the Grignard reaction.For example, diethyl ether, dioxane, ethers such as tetrahydrofuran, benzene, aromatic hydrocarbons such as toluene, pentane, Preferred examples include saturated hydrocarbons such as hexane, heptane and cyclohexane. The amount of compound (11) to be used is generally at least equimolar, preferably equimolar to 2-fold molar amount with respect to compound (1s). The above reaction is usually carried out at -70 to 100 ° C, preferably -30 to 70 ° C.
It is performed in the vicinity, and generally ends in about 1 to 50 hours.

The reaction for converting the compound (1r) into the compound (1u) is carried out under the same conditions as in the reaction of the compound (1h) with the compound (7) or the compound (8) in the above Reaction Scheme-4. ) And compound (7) or compound (8).

The reaction for converting the compound (1u) to the compound (1r) is carried out under the same conditions as in the hydrolysis reaction of the compound (1j) in the aforementioned Reaction Formula-5.

The reaction between compound (1s) and compound (11a) is carried out in a suitable solvent in the presence of a basic compound. Examples of the basic compound to be used include inorganic bases such as sodium metal, potassium metal, sodium hydride, sodium amide, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, and sodium hydrogen carbonate;
Metal alcoholates such as sodium methylate, sodium ethylate and potassium t-butoxide; alkyl and aryl lithium or lithium amides such as methyllithium, n-butyllithium, phenyllithium and lithium diisopropylamide; pyridine, piperidine, quinoline and triethylamine And organic bases such as N, N-dimethylaniline. As the solvent, any solvent can be used as long as it does not affect the reaction.Examples include ethers such as diethyl ether, dioxane, tetrahydrofuran, monoglyme, and diglyme; aromatic hydrocarbons such as benzene, toluene, and xylene; and n. Aliphatic hydrocarbons such as aliphatic hydrocarbons such as hexane, heptane and cyclohexane, amines such as pyridine and N, N-dimethylaniline, aprotic polar solvents such as N, N-dimethylformamide, dimethyl sulfoxide and hexamethylphosphoric triamide; Examples thereof include alcohols such as methanol, ethanol, and isopropanol, and a mixed solvent thereof.
The reaction temperature is usually -80 to 150 ° C, preferably -80.
The temperature is preferably about -120 ° C, and the reaction is generally completed in about 0.5 to 15 hours. The amount of compound (11a) to be used is at least equimolar, preferably equimolar to 10-fold molar quantity, relative to compound (1s).

[0681]

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[Wherein R ¹ , R ² , R ^3a , R ⁵ , m, n,
p ', A, r and X are the same as above. R ²⁰ is a lower alkyl group, a lower alkoxy-substituted lower alkyl group, a lower alkenyl group, a lower alkoxycarbonyl-substituted lower alkyl group,
A hydroxyl-substituted lower alkyl group, a carboxy-substituted lower alkyl group, a phenyl lower alkyl group which may have a group selected from the group consisting of a lower alkyl group and a lower alkoxy group as a substituent on a phenyl ring, a morpholino-substituted lower alkyl group, or The group -A ₁ -CO-NR ⁶ R ⁷ (A ₁ , R ⁶
And R ⁷ are the same as above. ). R ²¹ represents a lower alkoxy group, a lower alkoxy-substituted lower alkoxy group, or a phenyl lower alkoxy group which may have a substituent selected from the group consisting of a lower alkyl group and a lower alkoxy group on the phenyl ring. The reaction for converting the compound (1x) into the compound (1x ′) is carried out under the same conditions as those for converting the compound (1o) into the compound (1m) in the aforementioned Reaction Formula-6.

The reaction between compound (1x ′) and compound (12) is carried out under the same conditions as in the reaction between compound (1m) and compound (10) in the aforementioned Reaction Formula-6.

[0684]

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[0685]

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[Wherein R ¹ , R ^3a , R ⁸ , m, n, q ′,
R ⁵ , p ′, r and the group represented by the above [Formula 29] are the same as described above. R ²² represents a lower alkoxycarbonyl-substituted lower alkoxy group. R ²³ represents a carboxy-substituted lower alkoxy group. R ²⁴ represents a morpholinocarbonyl lower alkoxy group. R ²⁵ represents a group —OA ₁ -CO-NR ⁶ R ⁷ (A
₁ , R ⁶ and R ⁷ are the same as above. ). The reaction for converting the compound (1y) to the compound (1z) and the reaction for converting the compound (1B) to the compound (1C) are performed according to the above-mentioned reaction formula.
The reaction is performed under the same conditions as in the hydrolysis reaction of compound (1j) in 5.

The reaction between the compound (1z) and the compound (13) and the reaction between the compound (1C) and the compound (14) are the same as the reaction between the compound (2) and the compound (3) in the reaction formula-1. It is performed under conditions.

[0688]

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[Wherein R ¹ , R ² , R ⁸ , R ^3a , m, n,
q ′, R ¹² , R ⁵ , p ′, A, r and the group represented by the above [Formula 29] are the same as described above. The reaction for converting the compound (1j) to the compound (1G) and the reaction for converting the compound (1H) to the compound (1I) are performed according to the above-mentioned reaction formula.
The reaction is carried out under the same conditions as in the reaction for converting compound (1s) to compound (1r) in 8.

[0690]

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[Wherein R ¹ , R ² , R ^3a , R ⁵ , A, m,
^{n, p ', R 12,} r and X are as defined above. B represents a lower alkylene group. The reaction for converting the compound (1J) into the compound (1K) is carried out under the same conditions as those for converting the compound (1s) into the compound (1r) in the aforementioned Reaction Formula-8.

The reaction for converting the compound (1K) into the compound (1L) is carried out by reacting the compound (1K) with a halogenating agent in a suitable solvent or without solvent. Here, as the halogenating agent, mineral acids such as hydrochloric acid and hydrobromic acid,
Phenyl lower alkyl halides such as N, N-diethyl-1,2,2-trichlorovinylamide, phosphorus pentachloride, phosphorus pentabromide, phosphorus oxychloride, thionyl chloride, mesyl chloride or tosyl chloride and basic compounds, tetrachloride Examples thereof include carbon or carbon tetrabromide and triphenylphosphine. Here, as the basic compound, the reaction formula-1
Any of the basic compounds exemplified for the reaction of the carboxylic acid halide with the amine in the above can be used. Examples of the solvent used include ethers such as dioxane and tetrahydrofuran; halogenated hydrocarbons such as chloroform, methylene chloride and carbon tetrachloride; and aromatic hydrocarbons such as benzene, toluene and xylene. When a phenyl lower alkyl halide such as tosyl chloride and a basic compound are used as the halogenating agent, the molar ratio of the halogenating agent is at least equimolar to the compound (1K), preferably equimolar to 2 times. Good to use in quantity. When another halogenating agent is used, it is preferably used in an amount at least equimolar to the compound (1K), usually in a large excess. The reaction is completed usually at room temperature to 150 ° C., preferably at room temperature to 80 ° C., for about 1 to 80 hours.

The reaction of the compound (1L) with the compound (13) is carried out under the same conditions as in the reaction of the compound (1a) with the compound (4a) in the aforementioned reaction formula-2.

[0694]

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[Wherein R ¹ , R ² , R ^3a , r, m and n are as defined above. R ²⁶ represents a phenylthio-substituted lower alkyl group which may have a lower alkoxy group as a substituent on the phenyl ring. R ²⁷ represents a phenylsulfinyl-substituted lower alkyl group which may have a lower alkoxy group as a substituent on the phenyl ring. R ²⁸ represents a phenylsulfonyl-substituted lower alkyl group which may have a lower alkoxy group as a substituent on the phenyl ring. The reaction for converting the compound (1N) to the compound (1O) and the reaction for converting the compound (1O) to the compound (1P) are performed according to the above-mentioned reaction formula.
The reaction is carried out under the same conditions as in the reaction for converting compound (1c) into compound (1d) in 3.

The reaction for introducing the compound (1N) into the compound (1P) is carried out except that the amount of the oxidizing agent used is at least 2 times, preferably 2 to 4 times the mole of the compound (1N).
The reaction can be carried out under the same conditions as in the reaction for converting compound (1N) to compound (10).

[0697]

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[Wherein R ¹ , R ² , R ^3a , R ⁵ , m, n,
p ', X, A, A 1, r and Y are as defined above. R ^6a is a hydrogen atom, a lower alkyl group which may have a hydroxyl group as a substituent, a phenyl lower alkyl group which may have a lower alkoxy group as a substituent on a phenyl ring, a furyl lower alkyl group or a lower alkoxy-substituted lower alkyl group. Is shown. R ^6b represents R ^6a other than a hydrogen atom. R ^6c and R ^6d each represent a hydrogen atom or a lower alkyl group.
R ²⁹ represents a hydrogen atom or a lower alkyl group. R ³⁰ represents a lower alkyl group or a group —A ₁ CONR ⁶ R ⁷ (A ₁ , R ⁶ and R ⁷ are as defined above). R ^30a and R ^30b each represent a hydrogen atom or a lower alkyl group. However, when R ³⁰ represents a group —A ₁ CONR ⁶ R ⁷ , R ²⁹ represents a hydrogen atom. The reaction between the compound (1Q) and the compound (15a) and the reaction between the compound (1S) and the compound (16a) are the same as the reactions between the compound (1a) and the compound (4a) in the aforementioned Reaction Formula-2. It is performed under conditions. The reaction between the compound (1Q) and the compound (15b) and the reaction between the compound (1S) and the compound (16b) are carried out under the same conditions as those for the reaction between the compound (1a) and the compound (4b) in the aforementioned Reaction Formula-2. It is performed. The compound (2) or (3) as a starting material can be produced, for example, by the method shown in the following reaction formula.

[0699]

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[Wherein R ^3b is as defined above. However, compound group R ^3b of (3a) CH ₂ - group except for the annular portion R ^3b in R ^3b CH ₂ - is the sum of the carbon number of which shall not exceed 6. The reaction for converting the compound (17) into the compound (3a) can be carried out by reacting the compound (17) with hydrazine or hydrolyzing the compound (17) in a suitable solvent. As a solvent used in reacting hydrazine, any of the same solvents as used in the reaction between compound (2) and compound (3) in the above-mentioned reaction formula-1 can be used in addition to water. The reaction is usually carried out at room temperature to about 120 ° C., preferably 0 to 120 ° C.
The process is performed at about 100 ° C., and generally ends in about 0.5 to 10 hours. The amount of hydrazine to be used is at least about an equimolar amount to compound (17), preferably from equimolar to 5 moles.
The amount is preferably about twice the molar amount.

The above hydrolysis can be carried out in a suitable solvent or without a solvent in the presence of an acid or a basic compound. Examples of the solvent used include water, lower alcohols such as methanol, ethanol and isopropanol; ketones such as acetone and methyl ethyl ketone; ethers such as dioxane, tetrahydrofuran and ethylene glycol dimethyl ether; fatty acids such as acetic acid and formic acid; Solvents and the like can be mentioned. Examples of the acid include mineral acids such as hydrochloric acid, sulfuric acid and hydrobromic acid, and organic acids such as formic acid, acetic acid and aromatic sulfonic acid.Examples of the basic compound include sodium carbonate and potassium carbonate. Examples thereof include metal carbonates and metal hydroxides such as sodium hydroxide, potassium hydroxide, and calcium hydroxide. The reaction proceeds usually at room temperature to about 200 ° C., preferably at room temperature to about 150 ° C., and is generally completed in about 10 minutes to 25 hours.

[0702]

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[Wherein R ³¹ represents a hydrogen atom, a lower alkyl group or a lower alkenyl group. R ^3e is a hydrogen atom, a lower alkyl group, a group ^{- (D) r'-R 33} (.r showing a wherein D is a lower alkylene group "is 0 or 1 .R ³³ is a group

[0704]

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(R ⁵ and p are the same as defined above.), A lower alkanoyloxy-substituted lower alkyl group, a lower alkoxy lower alkyl group, a lower alkanoyl group-substituted lower alkyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl ring A benzoyl-substituted lower alkyl group which may have a halogen atom as a substituent, a group -E'-
R ⁵² R ⁵³ (R ⁵² and R ⁵³ are the same as above, E ′ represents a lower alkylene group), a group represented by the above formula (26), a cycloalkyl group, a naphthyl group or a group

[0706]

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(Wherein R ⁸ and q are as defined above.

[0708]

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Is a 5- to 14-membered monocyclic, dimeric or tricyclic saturated or unsaturated heterocyclic ring having 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur. Represents a group. ). ), A lower alkoxy group substituted with a lower alkoxy group, a halogen atom which may have a substituent selected from the group consisting of a lower alkanoyl group and a phenyl lower alkenylcarbonyl group on the phenyl ring. , tetrazolyl group which may have a lower alkyl group as a substituent on the tetrazole ring, a hydroxyl group, a group ^{_{-O-a 4 -CO-NR 40}} R 41
(A ₄ , R ⁴⁰ and R ⁴¹ are the same as described above), phenyl which may have a group selected from the group consisting of a lower alkenyloxy group, a nitro group and a lower alkyl group which may have a halogen atom as a substituent. Group, a lower alkoxy group having a substituent selected from the group consisting of a lower alkoxy group, a halogen atom, a lower alkanoyl group and a phenyl lower alkenylcarbonyl group as a substituent on a phenyl ring, a lower alkoxy group substituted with a lower alkoxy group , A tetrazolyl group which may have a lower alkyl group as a substituent on the tetrazole ring, a hydroxyl group, a group -OA ₄ -CO-N
R ⁴⁰ R ⁴¹ (A ₄ , R ⁴⁰ and R ⁴¹ are as defined above), a lower alkenyloxy group, a nitro group and a group selected from the group consisting of a lower alkyl group which may have a halogen atom as a substituent. Phenyl lower alkenyl group, phenylthio-substituted lower alkyl group which may have a lower alkoxy group as a substituent on the phenyl ring, phenylsulfinyl-substituted lower alkyl group which may have a lower alkoxy group as a substituent on the phenyl ring A phenylsulfonyl-substituted lower alkyl group which may have a lower alkoxy group as a substituent on the phenyl ring, a phenoxy-substituted lower alkyl group, a group -A ₅ -CR ⁴² R ⁴³ R
⁴⁴ (wherein A ₅ , R ⁴² , R ⁴³ and R ⁴⁴ are as defined above),
2,3-dihydro-1H- which may have on the 2,3-dihydro-1H-indenyl ring a group selected from the group consisting of an oxo group as a substituent, a hydroxyl group and a silyloxy group having a lower alkyl group as a substituent. An indenyl group-substituted lower alkyl group, a group represented by the above [Formula 34], or a group

[0710]

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(In the formula, R ⁴⁷ and u are the same as described above.)

[0712]

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Embedded image is a 5- to 14-membered mono-, di- or tri-cyclic saturated or unsaturated heterocyclic group having 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur Is shown. ). However, R ^3e may have a lower alkoxy group as a substituent, a halogen atom, a substituent selected from the group consisting of a lower alkanoyl group and a phenyl lower alkenylcarbonyl group as a substituent on the phenyl ring, an amino group and a lower alkoxy group. A lower alkoxy group, a tetrazolyl group which may have a lower alkyl group as a substituent on the tetrazole ring, a hydroxyl group, a group -OA ₄ -CO-N
R ⁴⁰ R ⁴¹ (A ₄ , R ⁴⁰ and R ⁴¹ are as defined above), a lower alkenyloxy group, a nitro group and a group selected from the group consisting of a lower alkyl group which may have a halogen atom as a substituent. A phenyl group which may be
7], R ³¹ represents a lower alkenyl group. Further, the group (R ^3e ) of the compound (3b)
In (R ³¹⁾ CH-, the sum of the number of carbon atoms contained in the group excluding the annular portion ^{R 3e (R 3e) (R} 31) CH- shall not exceed 6. R ³² represents a lower alkanoyloxy group. The reaction between the compound (18) and the compound (19) is carried out under the same conditions as in the reaction between the compound (1a) and the compound (4b) in the aforementioned Reaction Formula-2.

Compound (17) used as a starting material
Is produced, for example, by the method shown in the following reaction formula-17.

[0715]

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[Wherein R ^3b , R ¹² and X are as defined above. M
Represents an alkali metal atom such as potassium and sodium.
The sum of the carbon atoms of the compound (17) of the group -CH ₂ R ^3b group -CH ₂ R ^3b excluding the annular portion R ^3b in shall not exceed 6. The reaction for converting the compound (20) to the compound (21) is performed under the same conditions as in the halogenation reaction of the compound (1p) in the aforementioned Reaction Scheme-7, but 2- (4-biphenylyl) is added to the reaction system. It is preferable to add a radical initiator such as -5-phenyloxazole and azobisisobutyronitrile perbenzoic acid and an appropriate amount of water (for example, 3 mol%).

The reaction between the compound (21) and the compound (22a) is carried out under the same conditions as in the reaction between the compound (1a) and the compound (4a) in the aforementioned Reaction Scheme-2.

The reaction for converting the compound (23) into the compound (24) is carried out under the same conditions as in the reaction for converting the compound (1s) into the compound (1r) in the aforementioned Reaction Formula-8.

The reaction of compound (24) with compound (22b) is carried out in a suitable solvent in diethyl azodicarboxylate,
Dialkyl azodicarboxylates such as dibutyl azodicarboxylate, azodicarboxylic acid derivatives such as dialkyl azodicarboxamides such as 1,1'-azodicarbonyl dipiperidine, and trialkyl phosphines and triphenyl phosphines such as trimethyl phosphine And the like in the presence of a phosphorus compound such as a triarylphosphine. As the solvent used herein, any solvent other than lower alcohols among the solvents used in the reaction of compound (1a) with compound (4a) in the aforementioned Reaction Formula-2 can be used. The amount of the azodicarboxylic acid derivative, phosphorus compound and compound (22b) to be used is generally at least equimolar, preferably equimolar to 1.5-fold molar with respect to compound (24). The reaction is usually carried out at 0 to 100 ° C, preferably at 0 to 7 ° C.
The process is completed at about 0 ° C. in about 1 to 15 hours.

The reaction for converting the compound (25) into the compound (24) is carried out under the same conditions as those for converting the compound (1s) into the compound (1r) in the aforementioned Reaction Formula-8.

The reaction of the compound (26) with the compound (22a) is carried out in a suitable solvent in the presence of formaldehyde and an acid. As the solvent used herein, for example, dichloromethane, dichloroethane, chloroform, halogenated hydrocarbons such as carbon tetrachloride, water, methanol, ethanol, alcohols such as isopropanol, acetic acid,
Alkanoic acids such as propionic acid, acid anhydrides such as acetic anhydride,
Examples thereof include polar solvents such as acetone and dimethylformamide and the like and mixed solvents thereof. Examples of the acid to be used include hydrochloric acid gas, hydrochloric acid, and mineral acids such as hydrobromic acid. As the formaldehyde, an aqueous solution containing 20 to 40% by weight of formaldehyde, a trimer, a polypolymer (paraformaldehyde) and the like are usually used. Compound (22
The amount of a) to be used is usually at least equimolar, preferably equimolar to 2-fold molar amount with respect to compound (26). Formaldehyde is preferably used in an amount at least equimolar to the compound (26), usually in a large excess. The reaction is carried out usually at 0 to 200 ° C, preferably at room temperature to 1 ° C.
It proceeds suitably at around 50 ° C. and ends in about 0.5 to 24 hours.

[0722]

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[Wherein R ^3b is as defined above. The reaction for converting the compound (27) into the compound (3c) is carried out under the same conditions as the reaction for converting the compound (1s) into the compound (1r) in the aforementioned Reaction Formula-8.

[0724]

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[Wherein R ³⁴ is a group

[0726]

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Or a group -NR ³⁶ R ³⁷ (R ³⁶ and R ³⁷ each represent a phenyl lower alkyl group). R ³⁵ represents a phenylthio group or a phenoxy group which may have a lower alkoxy group as a substituent on the phenyl ring. A
Is the same as above. The reaction between compound (28) and compound (29) is carried out under the same conditions as in the reaction between compound (1a) and compound (4a) in the aforementioned Reaction Formula-2.

In the reaction for converting the compound (30) into the compound (3d), when R ^{34 in the} compound (30) represents a group represented by the above formula, the compound (17) in the above reaction formula -15 is converted to the compound (17). The reaction is carried out under the same conditions as in the reaction leading to compound (3a).

In the compound (30), when R ³⁴ represents a group —NR ³⁶ R ³⁷ , the compound (1o) in the above reaction formula-6 is converted to a compound (1m), and R ¹⁴ is a phenyl lower alkoxy group. The reaction is carried out under the same conditions as the reduction reaction of a certain compound.

[0730]

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[Wherein R ¹ , R ² , R ¹² and r are as defined above. The reaction between compound (31) and compound (32) is performed in the presence of a basic compound. As the basic compound used herein, the compound (1a) in the above Reaction Formula-2
Any of the basic compounds used in the reaction of the compound (4a) with the compound (4a) can be used. The compound (32) is usually used in an amount at least equimolar, preferably equimolar to 5-fold molar amount, relative to the compound (31). The reaction is completed usually at 0 to 100 ° C, preferably at about 0 to 70 ° C, for about 1 hour to 5 days.

The reaction for converting the compound (33a) to the compound (33b) is carried out in a suitable solvent in the presence of a phosphorus halide such as phosphorus tribromide or phosphorus trichloride. Examples of the solvent used include ethers such as dioxane and tetrahydrofuran, and halogenated hydrocarbons such as chloroform, methylene chloride and carbon tetrachloride. The phosphorus halide compound is preferably used in an equimolar to 2 times the molar amount of the compound (33a). The reaction is usually carried out at 0 to 100
C., preferably at about 0 to 70 ° C., in about 0.5 to 5 hours.

The reaction for converting the compound (33a) into the compound (33c) is carried out in a suitable solvent in the presence of an acid in the presence of the compound (33).
a) is reacted with sodium hydrosulfite. As the solvent used here,
Examples thereof include alcohols such as methanol, ethanol, propanol, butanol, 3-methoxy-1-butanol, ethyl cellosolve, and methyl cellosolve, and water. Examples of the acid used include mineral acids such as hydrochloric acid. The sodium hydrosulfite is usually used in an amount of at least equimolar, preferably equimolar to 5-fold molar amount, relative to compound (33a). The reaction is usually performed at 0 to 100 ° C, preferably at 0 to 70 ° C.
It ends in about 1 to 10 hours in the vicinity.

The reaction for converting the compound (33c) to the compound (33d) is carried out under the same conditions as in the reaction for converting the compound (1c) to the compound (1d) in the aforementioned Reaction Formula-3.

The reaction for converting the compound (33a) to the compound (33d) is similar to the compound (33a) except that a trialkyl phosphite such as trimethyl phosphite is used instead of the phosphorus halide compound as the phosphorus compound. The reaction is carried out under the same conditions as in the reaction leading to (33b), but an alcohol such as 1-propanol may be used as the solvent here, and the reaction temperature is usually from 0 to 15
It is good to carry out at 0 ° C, preferably around 0-100 ° C.

[0736]

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[Wherein R ¹ , R ² , R ¹² , r, m and n are as defined above. The hydrolysis reaction of compound (33) is performed under the same conditions as the hydrolysis reaction of compound (1j) in the aforementioned Reaction Formula-5.

The esterification of the compound (2) is carried out by, for example, reacting the starting compound with methanol, in the presence of a mineral acid such as hydrochloric acid or sulfuric acid, or a halogenating agent such as thionyl chloride, phosphorus oxychloride, phosphorus pentachloride or phosphorus trichloride. The reaction is carried out by reacting with alcohols such as ethanol and isopropanol usually at 0 to 150 ° C, preferably 50 to 100 ° C for about 5 minutes to 10 hours.

The intermediate compound (24a) can also be produced by the method shown in the following reaction formula-22.

[0740]

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[Wherein R ⁸ , q ′ and R ¹² are as defined above. The reaction for converting the compound (20a) to the compound (20b) is performed in a suitable solvent in the presence of an oxidizing agent. As the solvent and the oxidizing agent used here, any of the solvent and the oxidizing agent used in the reaction for converting the compound (1c) into the compound (1d) in the above Reaction Formula-3 can be used. The oxidizing agent is usually preferably used in a large excess amount relative to the compound (20a). The reaction is carried out usually at room temperature to 150 ° C., preferably at room temperature to 120 ° C.
The process is completed in about 1 to 20 hours at about ° C.

The reaction for converting the compound (20b) into the compound (20c) can be carried out in a compound represented by the general formula R ¹² COOCOR ¹² (R ¹² is as defined above), usually at room temperature to 200 ° C.
It is preferably carried out by heating at room temperature to about 150 ° C. for 1 to 10 hours.

The reaction for converting the compound (20c) into the compound (24a) is carried out under the same conditions as in the hydrolysis reaction of the compound (1j) in the aforementioned Reaction Formula-5.

The compound of the general formula (1) in which R ⁵ or R ⁸ represents an amino group can be produced by reducing the corresponding compound in which R ⁵ or R ⁸ represents a nitro group.

The reduction reaction is carried out, for example, by reduction using a catalytic reduction catalyst in a suitable solvent or in a suitable inert solvent with a metal or metal salt and an acid or a metal or metal salt and an alkali metal hydroxide, sulfide or the like. And a mixture with an ammonium salt or the like as a reducing agent.

When the reduction catalyst is used, examples of the solvent used include water, alcohols such as acetic acid, methanol, ethanol and isopropanol, hydrocarbons such as hexane and cyclohexane, dioxane, tetrahydrofuran, diethyl ether and diethylene glycol dimethyl ether. And esters such as ethyl acetate and methyl acetate; aprotic polar solvents such as N, N-dimethylformamide; and mixed solvents thereof. Examples of the catalytic reduction catalyst used include palladium, palladium-black, palladium-carbon, platinum, platinum oxide, copper chromite, and Raney-nickel. Generally, the catalyst is preferably used in an amount of about 0.02 to 1 times the amount of the starting material. The reaction temperature is usually -20 to 150
℃, preferably 0-100 ℃, hydrogen pressure is usually 1
The reaction is generally between 0.5 and 1 atmosphere.
It ends in about 0 hours. Further, an acid such as hydrochloric acid may be added to the reaction.

In the case of using another method, iron, zinc, tin or stannous chloride and a mineral acid such as hydrochloric acid or sulfuric acid, or iron, ferrous sulfate, zinc or tin and an alkali metal hydroxide such as sodium hydroxide or the like are used. And a mixture with a sulfide such as ammonium sulfide, ammonia water, and an ammonium salt such as ammonium chloride are used as the reducing agent. As the inert solvent used, for example, water, acetic acid, methanol, ethanol,
Examples thereof include dioxane. Conditions for the reduction reaction may be appropriately selected depending on the reducing agent used. For example, when stannous chloride and hydrochloric acid are used as the reducing agent, the temperature is preferably 0 ° C. to around room temperature, about 0.5 to 10 hours. It is better to carry out the reaction. The reducing agent is used at least in an equimolar amount, usually in an equimolar to 5-fold molar amount, relative to the raw material compound.

[0748]

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[Wherein R ¹ , R ² , R ^3a , R ⁸ , R ³⁹ ,
m, n, q ', D, r, r' and the group represented by the above [Formula 29] are the same as described above. R ⁴⁸ represents a lower alkoxy group.
R ⁴⁹ represents lower alkoxycarbonyl. R ⁵⁰ and R ⁵¹
Represents the same or different and represents a hydrogen atom or a lower alkyl group. The reaction between compound (1U) and compound (34) is carried out in the presence of a basic compound in a suitable solvent. As the basic compound to be used, inorganic bases such as sodium metal, potassium metal, sodium hydride, sodium amide, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, sodium methylate, sodium ethylate , Potassium tert-butoxide and other metal alcoholates, methyllithium, n-butyllithium, phenyllithium, lithium diisopropylamide and other alkyl and aryllithium or lithium amides, pyridine, piperidine, quinoline, triethylamine, N, N-dimethylaniline And the like. As the solvent, any solvent can be used as long as it does not affect the reaction, for example, ethers such as diethyl ether, dioxane, tetrahydrofuran, monoglyme, diglyme, benzene, toluene,
Aromatic hydrocarbons such as xylene, n-hexane, heptane, aliphatic hydrocarbons such as cyclohexane, pyridine,
Examples include amines such as N, N-dimethylaniline, aprotic polar solvents such as N, N-dimethylformamide, dimethylsulfoxide, and hexamethylphosphoric triamide, and alcohols such as methanol, ethanol, and isopropanol. The reaction temperature is usually -80 to 150 ° C,
The temperature is preferably around -80 to 120 ° C, and the reaction is generally completed in about 0.5 to 15 hours.

The reaction for converting the compound (1V) into the compound (1W) can be carried out under the same reaction conditions as in the hydrolysis reaction of the compound (1j) in the aforementioned Reaction Formula-5.

The reaction between the compound (1W) and the compound (35) can be carried out under the same reaction conditions as the reaction between the compound (2) and the compound (3) in the aforementioned Reaction Formula-1.

[0752]

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[Wherein R ¹ , R ² , m, n, r and R ^3a are the same as above. R ^{3c ′} is a phenyl lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxycarbonyl group, a phenoxycarbonyl group or a group —CO-ANR ⁵² R
⁵³ (R ⁵² , R ⁵³ and A are as defined above). The reaction between the compound (1a) and the compound (38) can be carried out under the same reaction conditions as the reaction between the compound (2) and the compound (3) in the aforementioned reaction formula-1. Here, the reaction between the carboxylic anhydride and the amine is usually performed in the presence of the same solvent and basic compound as the reaction using the active ester method in the reaction between the compound (2) and the compound (3), which is usually 0 to 150.
C., preferably at 10 to 100.degree.
Complete in 30 hours. The amount of the carboxylic anhydride to be used is at least equimolar, preferably equimolar to 2 times the molar amount of compound (1a).

The compound of the general formula (1) in which R ⁸ represents a lower alkanoyl group is the same as the compound in which the corresponding R ⁸ represents a cyano group, except that the compound of the general formula R ¹⁷ MgX (11) (R ¹⁷ and X are as defined above). )), And then hydrolyzed. The reaction between the compound (1) and the compound (11) is performed under the same conditions as in the reaction between the compound (1s) and the compound (11) in the aforementioned Reaction Formula-8. The subsequent hydrolysis reaction is performed under the same conditions as in the hydrolysis reaction of compound (1j) in the aforementioned Reaction Formula-5. The reaction is preferably performed in the presence of an acid.

R ⁵ represents a 1,3-dioxolanyl group which may have a lower alkyl group as a substituent or R ⁸ represents a 1,3-dioxolanyl-substituted lower alkyl group which may have a lower alkyl group as a substituent. In the compound of the formula (1), the corresponding R ⁵ is a lower alkanoyl group or R ⁸
Is a compound having a lower alkanoyl group-substituted lower alkyl group,

[0756]

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(Wherein R ³⁸ represents a lower alkyl group; v represents an integer of 0 or 1 to 3). The reaction is carried out in a suitable solvent in the presence of an acid. As the solvent used herein, in addition to halogenated hydrocarbons such as methylene chloride, dichloroethane, and chloroform, the above-mentioned reaction formula-
Any of the solvents used for compound (1a) and compound (4a) in 2 can be used. Examples of the acid used include mineral acids such as hydrochloric acid, sulfuric acid, and hydrobromic acid, and organic acids such as p-toluenesulfonic acid. Compound (36) is usually at least equimolar to the starting material,
Preferably, it is used in an equimolar to 10-fold molar amount. The reaction is carried out usually at room temperature to 150 ° C., preferably at room temperature to 100 ° C.
It ends in about 1 to 24 hours at around ° C.

R ⁵ represents a lower alkanoyl group or R ⁸ represents a lower alkanoyl group-substituted lower alkyl group represented by the following general formula (1):
Is a compound in which the corresponding R ⁵ may have a lower alkyl group as a substituent, for example, a 1.3-dioxolanyl group or R
It can be obtained by hydrolyzing a compound in which ⁸ is a 1,3-dioxolanyl-substituted lower alkyl group which may have a lower alkyl group as a substituent. The hydrolysis reaction can be performed in a suitable solvent in the presence of an acid. As the solvent used here, for example,
Examples thereof include water, lower alcohols such as methanol, ethanol and isopropanol, ketones such as acetone and methyl ethyl ketone, halogenated hydrocarbons such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and mixed solvents thereof. Examples of the acid include mineral acids such as hydrochloric acid, sulfuric acid, and hydrobromic acid, and organic acids such as p-toluenesulfonic acid. The reaction is usually carried out at 0 to 70 ° C, preferably at 0 ° C to around room temperature,
It ends in about 1 to 10 hours.

[0759] formula showing a Ratorazoriru group R ⁸ is having a lower alkyl group or a lower alkoxy-lower alkyl group as a substituent the compounds of (1) is a compound corresponding R ⁸ is tetrazolyl general formula R ³⁹ X ( 37) (where R
³⁹ represents a lower alkyl group or a lower alkoxy lower alkyl group. X is the same as above. )) Under the same conditions as in the reaction of the compound (10) with the compound (4a) in the above Reaction Scheme-2.

The compound of the general formula (1) in which R ⁸ represents an unsubstituted tetrazolyl group is a compound in which the corresponding R ⁸ is a tetrazolyl group having a lower alkoxy lower alkyl group as a substituent in the aforementioned reaction formula-6. It is produced by hydrolysis under the same conditions as in the hydrolysis reaction of compound (1o) wherein R ¹⁴ is a lower alkoxy-substituted lower alkoxy group.

The compound of the general formula (1) in which R ² represents a morpholino-substituted lower alkyl group or an imidazolyl-substituted lower alkyl group comprises a compound in which R ² represents a lower alkyl group having a halogen atom and morpholine or imidazole. It is produced by reacting under the same conditions as the reaction between compound (1a) and compound (4a) in the above-mentioned reaction formula-2.

The compound of the general formula (1) in which R ² represents a halogen-substituted methyl group is obtained by converting a compound in which R ² is a methyl group into a compound (21) by converting the compound (20) in the aforementioned reaction formula-17 It is produced by reacting under the same conditions as described above. When the halogen atom in the halogen-substituted methyl group is a fluorine atom, it is also produced by reacting a compound of the general formula (1) showing a halogen-substituted methyl group other than the corresponding fluorine atom with silver fluoride.

Of the compounds of the present invention represented by the general formula (1), compounds having a basic group can be easily converted to acid addition salts by reacting with a pharmaceutically acceptable acid. Examples of the acid include inorganic acids such as hydrochloric acid, sulfuric acid, phosphoric acid, and hydrobromic acid, oxalic acid, acetic acid, succinic acid, malonic acid, methanesulfonic acid, maleic acid, fumaric acid, malic acid, tartaric acid, and citric acid. And organic acids such as benzoic acid.

Of the compounds of the present invention represented by the general formula (1), compounds having an acidic group can be easily converted into salts by reacting with a pharmaceutically acceptable basic compound. Examples of the basic compound include sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate, potassium hydrogen carbonate and the like.

The target compound in each step thus obtained can be easily isolated and purified by ordinary separation means. As the separation means, for example, a solvent extraction method,
Examples thereof include a dilution method, a recrystallization method, column chromatography, and preparative thin-layer chromatography.

The compounds of the present invention also include optical isomers and stereoisomers.

The compound of the formula (1) is usually used in the form of a general pharmaceutical preparation. The preparation is prepared using a diluent or excipient such as a filler, a bulking agent, a binder, a humectant, a disintegrant, a surfactant and a lubricant, which are usually used. Various forms can be selected as the pharmaceutical preparation depending on the purpose of treatment. Representative examples are tablets, pills, powders, solutions, suspensions, emulsions, granules, capsules, suppositories, injections ( Liquid, suspension, etc.). In molding into tablets, those conventionally known in the art can be widely used as carriers, for example, lactose, sucrose, sodium chloride,
Glucose, urea, starch, calcium carbonate, kaolin, crystalline cellulose, excipients such as silicic acid, water, ethanol, propanol, simple syrup, glucose solution, starch solution, gelatin solution, carboxymethylcellulose, shellac, methylcellulose, potassium phosphate , Polyvinylpyrrolidone and other binders, disintegrators such as dried starch, sodium alginate, agar powder, laminaran powder, sodium bicarbonate, calcium carbonate, polyoxyethylene sorbitan fatty acid esters, sodium lauryl sulfate, stearic acid monoglyceride, starch, lactose , White sugar,
Disintegration inhibitors such as stearin, cocoa butter, hydrogenated oil, etc., absorption promoters such as quaternary ammonium bases, sodium lauryl sulfate, humectants such as glycerin and starch, starch, lactose, kaolin, bentonite, colloidal silicic acid, etc. And a lubricant such as purified talc, stearate, boric acid powder, polyethylene glycol and the like. Further, the tablets can be made into tablets coated with a usual coating, if necessary, such as sugar-coated tablets, gelatin-coated tablets, enteric-coated tablets, film-coated tablets or double tablets or multilayer tablets. In molding into a pill form, those conventionally known in the art can be widely used as carriers, for example, excipients such as glucose, lactose, starch, cocoa butter, hydrogenated vegetable oil, kaolin, talc, gum arabic powder, Examples include binders such as tragacanth powder, gelatin and ethanol, and disintegrants such as laminaran agar. For shaping in the form of suppositories, conventionally known carriers can be widely used, and examples thereof include polyethylene glycol, cocoa butter, higher alcohols, esters of higher alcohols, gelatin, and semi-synthetic glycerides. When prepared as an injection, the solution and suspension are preferably sterilized and isotonic with blood, and when formed into the form of these solutions, emulsions and suspensions, they may be used as diluents. Any of those commonly used in the field can be used, and examples thereof include water, ethyl alcohol, propylene glycol, ethoxylated isostearyl alcohol, polyoxylated isostearyl alcohol, and polyoxyethylene sorbitan fatty acid esters. In this case, a sufficient amount of salt, glucose or glycerin to prepare an isotonic solution may be contained in the pharmaceutical preparation, and a usual solubilizing agent, buffer, soothing agent and the like may be added. You may. If necessary, colorants, preservatives, fragrances,
Flavoring agents, sweetening agents, and other pharmaceuticals may be included in the pharmaceutical preparation.

The amount of the compound of the general formula (1) of the present invention or a salt thereof to be contained in the pharmaceutical preparation is not particularly limited and may be appropriately selected from a wide range.
The content is preferably 0% by weight.

The method of administration of the above pharmaceutical preparation is not particularly limited, and it is administered in accordance with various preparation forms, age, sex and other conditions of the patient, degree of disease and the like. For example, tablets, pills, solutions, suspensions, emulsions, granules and capsules are orally administered. In the case of an injection, it may be administered intravenously, alone or as a mixture with a normal replenisher such as glucose or amino acid, and if necessary, intramuscularly, intradermally, subcutaneously or intraperitoneally. Suppositories are administered rectally.

The dose of the above-mentioned pharmaceutical preparation is appropriately selected depending on the usage, the age of the patient, gender and other conditions, the degree of the disease and the like. Is about 0.2-200 per kg of body weight per day
It is good to be about mg.

Formulation Example 1 2- (2-benzofuranylmethylaminocarbonyl) -3-methylquinoxaline-4-oxide 5 mg Starch 132 mg Magnesium stearate 18 mg Lactose 45 mg Total 200 mg One tablet in a conventional manner, tablets of the above composition Was manufactured.

Formulation Example 2 2- [3- (4-methoxyphenyl) propylaminocarbonyl] -3-methylquinoxaline-4-oxide 150 mg Avicel (trade name, manufactured by Asahi Kasei Corporation) 40 g Corn starch 30 g Magnesium stearate 2 g Hydroxy Propylmethylcellulose 10 g Polyethylene glycol-6000 3 g Castor oil 40 g Methanol 40 g The compound of the present invention, Avicel, corn starch and magnesium stearate are mixed and polished, and then tableted with sugar coated R10 mm kine. The obtained tablets are coated with a film coating agent comprising hydroxypropylmethylcellulose, polyethylene glycol-6000, castor oil and methanol to produce film-coated tablets.

Reference Example 1 2-ethoxycarbonyl-3-methylbenzofuran
0 g of anhydrous diethyl ether solution (10 ml) was mixed with lithium aluminum hydride (0.93 g) in diethyl ether (30 m).
The suspension was added dropwise to the suspension under ice-cooling. After stirring at room temperature for 30 minutes,
Cool, decompose with saturated aqueous sodium sulfate, filter through celite, and dry over anhydrous sodium sulfate. The solvent was distilled off to give 3.7 g of 2-hydroxymethyl- as a white powder.
3-Methylbenzofuran was obtained.

¹ H-NMR (CDCl ₃ ) δ ppm;
1.82 (1H, t, J = 6 Hz), 2.27 (3H,
S), 4.76 (2H, d, J = 6 Hz), 7.20-
7.55 (4H, m).

Reference Example 2 3.7% of 2-hydroxymethyl-3-methylbenzofuran
g, 6.6 g of triphenylphosphine and 3.7 g of phthalimide were suspended in 40 ml of tetrahydrofuran, and a solution of 4.4 g of diethyl azodicarboxylate in 10 ml of tetrahydrofuran was added dropwise under ice cooling, followed by stirring at room temperature overnight. The solvent was distilled off, the residue was purified by silica gel chromatography (elution solvent: methylene chloride), crystallized by adding diethyl ether, collected by filtration and dried to obtain 4.6 as a white powder.
g of 3-methyl-2-phthalimidomethylbenzofuran were obtained.

¹ H-NMR (CDCl ₃ ) δ ppm;
2.40 (3H, s), 4.97 (2H, s), 7.1
0-7.30 (2H, m), 7.40 (1H, d, J =
7 Hz) 7.48 (1 H, d, J = 7 Hz), 7.65
−7.75 (2H, m), 7.80-7.90 (2H,
m).

Reference Example 3 3-Methyl-2-phthalimidomethylbenzofuran
6 g was added to 80 ml of methanol, 1.2 g of hydrazine hydrate was added, and the mixture was circulated for 3 hours. The solvent was distilled off, and a diluted aqueous sodium hydroxide solution was added to the residue, followed by extraction with chloroform. The chloroform layer was washed with saturated saline and then dried over anhydrous sodium sulfate. The solvent was distilled off to obtain 3.0 g of 2-aminomethyl-3-methylbenzofuran as a colorless transparent liquid.

¹ H-NMR (CDCl ₃ ) δ ppm;
1.55 (2H, brs), 2.21 (3H, s),
3.93 (2H, s), 7.15-7.30 (2H,
m), 7.35-7.50 (2H, m).

Reference Example 4 4.0 g of 2-methylbenzothiophene, 4.8 g of N-bromosuccinimide and 0.3 g of azobisisobutyronitrile were added to 50 ml of carbon tetrachloride and refluxed for 5 hours. After cooling, the insolubles were filtered off and concentrated. 2 as brown powder
6.7 g of -bromomethylbenzothiophene were obtained.

¹ H-NMR (CDCl ₃ ) δ ppm;
4.79 (2H, s), 7.30-7.45 (2H,
m), 7.36 (1H, s), 7.70-7.85 (2
H, m).

Reference Example 5 6.7 g of 2-bromomethylbenzothiophene was dissolved in 40 ml of dimethylformamide, and 5.0 g of potassium phthalimide was added, followed by stirring at 60 ° C. for 2 hours. Dimethylformamide was distilled off, the residue was extracted with chloroform, washed with water and saturated saline, and dried over anhydrous sodium sulfate.
The solvent was distilled off, diethyl ether was added to the residue, and the crystals were collected by filtration and dried to obtain 4.5 g of 2-phthalimidomethylbenzothiophene as a light brown powder.

[0782] _{^{1 H-NMR (CDCl 3)}} δppm;
5.10 (2H, s), 7.20-7.40 (3H,
m), 7.70-7.80 (4H, m), 7.80-
7.95 (2H, m).

Reference Example 6 4.3 g of 3-formylbenzofuran was added to 50 m of methanol.
1 g of sodium borohydride under ice-cooling.
Was gradually added. After stirring at the same temperature for 1 hour, methanol was distilled off, the residue was extracted with chloroform, washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain 4.1 g of 3-hydroxymethylbenzofuran as a pale yellow liquid.

¹ H-NMR (CDCl ₃ ) δ ppm;
1.62 (1H, t, J = 5 Hz), 4.85 (2H,
d, J = 5 Hz), 7.20-7.45 (2H, m),
7.53 (1H, d, J = 8 Hz), 7.62 (1H, d, J = 8 Hz)
s), 7.68 (1H, d, J = 8 Hz).

Reference Example 7 An anhydrous toluene solution of 3.46 g of ethyl 2-benzofuran acrylate was cooled to −50 ° C., and diisobutylaluminum hydride (1 M solution in toluene, 37 ml) was added dropwise. After stirring at −20 ° C. for 1 hour, methanol 30 ml
And stirred at room temperature overnight. The precipitate was filtered through celite and concentrated. The residue was dissolved in ethyl acetate, filtered with Florisil, and concentrated to obtain 2.6 g of colorless liquid 2- (3-hydroxy-1-propenyl) benzofuran.

[0786] ¹ H-NMR (CDCl ₃ ) δ ppm;
4.39 (2H, brs), 6.60 (3H, m),
7.17-7.32 (2H, m), 7.43 (1H,
d, J = 7 Hz), 7.52 (1H, d, J = 7H)
z).

Reference Example 8 Hydrogen chloride gas was introduced into a mixture of 13.4 g of benzothiophene and 15 ml of an aqueous solution of 37% formaldehyde under ice cooling (about 20 to 30 minutes). The mixture was further stirred at room temperature for 2 hours. The reaction solution was poured into ice water and extracted with diethyl ether. The obtained organic layer was washed with saturated sodium hydrogen carbonate and then dried over anhydrous sodium sulfate. The solvent was distilled off, and the obtained residue and 18.5 g of potassium phthalimide were dissolved in 100 ml of dimethylformamide.
Heated for hours. After cooling, the mixture was poured into ice water and the precipitated crystals were collected by filtration. The obtained crystals were washed with diisopropyl ether to give 3-phthalimidomethylbenzothiophene 1 as pale brown crystals.
3.4 g were obtained.

¹ H-NMR (CDCl ₃ ) δ ppm;
5.08 (2H, s), 7.3-7.5 (2H, m),
7.61 (1H, S), 7.6-7.9 (5H, m),
8.15 (1H, d, J = 8 Hz).

Reference Example 9 3.2 g of 2-acetylbenzofuran was added to 60 m of methanol.
Then, 15 g of ammonium acetate and 1.26 g of sodium cyanoborohydride were added. After stirring at room temperature overnight, dilute hydrochloric acid ice solution was added to make the mixture acidic, and the mixture was washed with ethyl acetate. The aqueous layer was made alkaline with an aqueous sodium hydroxide solution and extracted with chloroform. After washing the chloroform layer with water, chloroform dried over anhydrous sodium sulfate was distilled off to obtain 1.8 g of 2- (1-aminoethyl) benzofuran as a colorless liquid.

¹ H-NMR (CDCl ₃ ) δ ppm;
1.52 (3H, d, J = 6 Hz), 1.83 (2H,
brs), 4.20 (1H, q, J = 6 Hz), 6.5
0 (1H, s), 7.15-7.30 (2H, m),
7.43 (1H, d, J = 8 Hz), 7.51 (1H, d, J = 8 Hz)
d, J = 8 Hz).

Reference Example 10 25 g of 5-ethyl-2-methylpyridine was treated with 200 m of acetic acid.
and add 25 ml of 30% aqueous hydrogen peroxide solution,
Heated to 100 ° C. After 4 hours, 25 ml of a 30% aqueous hydrogen peroxide solution was further added, and the mixture was heated and stirred at the same temperature for 14 hours. After cooling, water was added several times to concentrate, and the finally obtained residue was neutralized by adding a saturated aqueous solution of potassium carbonate and extracted with chloroform. After drying over anhydrous potassium carbonate, the solvent was distilled off. The obtained residue was dissolved in 200 ml of acetic anhydride and heated at 120 ° C. for 4 hours. After evaporating the solvent, a saturated aqueous solution of sodium hydrogen carbonate was added, and the mixture was extracted from ethyl acetate. After drying over anhydrous sodium sulfate, the solvent was distilled off. The residue was dissolved in 200 ml of methanol, and potassium carbonate 57
g was added and stirred at room temperature for 12 hours. After evaporating the solvent, water was added, extracted from chloroform, and dried over anhydrous potassium carbonate. After evaporating the solvent, the obtained residue was subjected to silica gel column chromatography (elution solvent; ethyl acetate: n-ethyl acetate).
Hexane = 1: 4) to give a light brown liquid 5-ethyl-
20.4 g of 2-hydroxymethylpyridine were obtained.

¹ H-NMR (CDCl ₃ ) δ ppm;
1.26 (3H, t, J = 8 Hz), 2.66 (2H,
q, J = 8 Hz), 3.67 (1H, br), 4.73
(2H, s), 7.18 (1H, d, J = 8 Hz),
7.52 (1H, d, J = 8 Hz), 8.41 (1H,
s).

Reference Example 11 4- (2-methyl-1.3-dioxolan-2-yl)
Dissolve 1.9 g of benzonitrile in 20 ml of diethyl ether and add 400 m of lithium aluminum hydride at 0 ° C.
g was added. After performing the reaction at room temperature for 14 hours, 1 ml of water and 3 ml of an 8 mol aqueous sodium hydroxide solution were added to the reaction solution.
Was added. Further, magnesium sulfate was added, and insolubles were removed by filtration. The solvent was concentrated to give a colorless oil [4- (2-methyl-
1.3 g (1.3-dioxolan-2-yl) benzyl] amine were obtained.

¹ H-NMR (CDCl ₃ ) δ ppm;
7.45 (2H, d, J = 8 Hz), 7.29 (2H, d, J = 8 Hz)
d, J = 8 Hz), 4.04 (2H, m), 3.87
(2H, s), 3.77 (2H, m), 1.77 (2
H, br), 1.65 (3H, s).

Reference Example 12 13 g of N-bromoethylphthalimide and 7.9 g of p-methoxythiophenol were added to 70 m of dimethylformamide.
and 10 g of potassium carbonate was added thereto, followed by stirring at 70 ° C. overnight. Dimethylformamide was distilled off, the residue was extracted with diethyl ether, washed with water, and dried over anhydrous sodium sulfate. The diethyl ether was distilled off, crystallized from n-hexane, collected by filtration and dried to give 13.9 g of N-
[2- (4-Methoxyphenylthio) ethyl] phthalimide was obtained.

¹ H-NMR (CDCl ₃ ) δ ppm;
3.14 (2H, t, J = 7 Hz), 3.75 (3H,
s), 3.89 (2H, t, J = 7 Hz), 6.80
(2H, d, J = 8 Hz), 7.42 (2H, d, J =
8 Hz), 7.65-7.75 (2H, m), 7.75
７7.90 (2H, m).

Reference Example 13 N- (2-chloroethyl) dibenzylamine hydrochloride 2
5 g and 8.0 g of phenol in dimethylformamide 1
The mixture was dissolved in 00 ml, potassium carbonate (30 g) was added, and the mixture was stirred at 70 ° C. for 6 hours. Dimethylformamide was distilled off, the residue was extracted with diethyl ether, washed with water and dried over anhydrous sodium sulfate. Diethyl ether was distilled off to obtain 25.5 g of N- (2-phenoxyethyl) dibenzylamine as a colorless oil.

[0798] ¹ H-NMR (CDCl ₃ ) δ ppm;
2.90 (2H, t, J = 6 Hz), 3.72 (4H,
s), 4.03 (2H, t, J = 6 Hz), 6.80
(2H, d, J = 8 Hz), 6.85-7.00 (1
H, m), 7.15-7.45 (12H, m).

Reference Example 14 N- (2-phenoxyethyl) dibenzylamine 25.
5 g was dissolved in 500 ml of ethanol, 3.0 g of 10% palladium carbon was added, and hydrogenated at 50 ° C. and 1 atm. The catalyst was removed by filtration, and ethanol was distilled off to obtain 11.0 g of 2-phenoxyethylamine as a colorless oil.

¹ H-NMR (CDCl ₃ ) δ ppm;
1.47 (2H, brs), 3.08 (2H, t, J =
5 Hz), 4.01 (2H, t, J = 5 Hz), 6.8
5-7.00 (3H, m), 7.25 to 7.35 (2
H, m).

Reference Example 15 216 g of benzofuroxane and 207 of ethyl acetoacetate
g was added to 1.5 liters of triethylamine and stirred at room temperature for 4 days. The precipitated crystals were collected by filtration, washed with water, dried and recrystallized from ethyl acetate to give 115 g of 2-ethoxycarbonyl-.
3-Methylquinoxaline-1.4-dioxide was obtained as pale yellow needles. m. p. 137-138 ° C.

Reference Example 16 2-ethoxycarbonyl-3-methylquinoxaline-
77 g of 1,4-dioxide was dissolved in 3.5 liter of ethanol and 200 ml of concentrated hydrochloric acid, and an aqueous solution (1 liter) of 200 g of sodium hydrosulfite was stirred at room temperature.
Was added dropwise. After stirring at the same temperature for 4 hours, the reaction solution was neutralized with sodium hydrogen carbonate, and ethanol was distilled off. Water was added to the residue, and the precipitated crystals were collected by filtration, washed with water, dried, and then recrystallized from n-pentane to give colorless needles of 2-ethoxycarbonyl-3.
67 g of methylquinoxaline were obtained. m. p. 74-7
5 ° C.

Reference Example 17 2-ethoxycarbonyl-3-methylquinoxaline 64
g of methylene chloride was dissolved in 700 ml of methylene chloride, and 70 g of metachloroperbenzoic acid was gradually added under ice cooling. After stirring at room temperature overnight, the reaction solution was washed with a diluted aqueous solution of sodium thiosulfate, a saturated aqueous solution of sodium hydrogen carbonate and water in that order, and dried over anhydrous sodium sulfate. The solvent was distilled off, n-hexane was added to the residue, and the crystals were collected by filtration, dried and then recrystallized from n-hexane-diethyl ether to give colorless needles of 2-ethoxycarbonyl-3-methylquinoxaline-4-oxide. 45 g were obtained. m. p. 91-9
3 ° C.

Reference Example 18 2-ethoxycarbonyl-3-methylquinoxaline-
1.5 g of 4-dioxide in 500 ml of chloroform
, And 44 ml of phosphorus tribromide was gradually added dropwise under ice-cooling. After stirring at room temperature for 1 hour, chloroform was distilled off, and the residue was poured into ice water and neutralized with potassium carbonate. It was extracted with chloroform, washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by silica gel chromatography (elution solvent: n-hexane: ethyl acetate = 2: 1).
The crystals were recrystallized from ethyl acetate-n-hexane to obtain 35 g of 2-ethoxycarbonyl-3-methylquinoxaline-1-oxide as colorless prisms. m. p. 85-87
° C.

Reference Example 19 2-ethoxycarbonyl-3-methylquinoxaline-4
-Oxide (4.0 g) was suspended in methanol (80 ml) and 5N-sodium hydroxide aqueous solution (10 ml), and the mixture was stirred at room temperature for 3 hours. The methanol was distilled off. The precipitated crystals were collected by filtration as hydrochloric acid, washed with water and dried to obtain 3.2 g of 2-g as a white powder.
Carboxy-3-methylquinoxaline-4-oxide was obtained. m. p. 143-145 ° C (decomposition).

Reference Example 20 2.0 g of 2-carboxyquinoxaline was added to methanol 20
Then, 1.3 ml of thionyl chloride was added dropwise under ice-cooling. After refluxing for 15 minutes, methanol was distilled off, the residue was extracted with chloroform, washed with saturated aqueous sodium hydrogen carbonate and dried over anhydrous sodium sulfate. The solvent was distilled off, and the obtained 2-methoxycarbonylquinoxaline was dissolved in 40 ml of methylene chloride.
Under stirring at room temperature, 2.9 g of metachloroperbenzoic acid was added, and the mixture was stirred overnight at room temperature. The reaction solution was washed with a diluted aqueous solution of sodium thiosulfate and a saturated aqueous solution of sodium bicarbonate, and dried over anhydrous sodium sulfate. The solvent was distilled off, n-hexane was added to the residue for crystallization, followed by filtration and drying to obtain 2.0 g of 2-methoxycarbonylquinoxaline-4-oxide as a yellow powder. m.
p. 154-155 ° C.

Reference Example 21 2-ethoxycarbonyl-3-methylquinoxaline
2 g was dissolved in carbon tetrachloride (40 ml), N-bromosuccinimide (2.7 g) and perbenzoic acid (0.2 g) were added, and the mixture was heated under reflux for 8 hours. After evaporating the solvent, water was added, and the mixture was extracted with dichloromethane. After drying over anhydrous sodium sulfate, the solvent was distilled off. The obtained residue was dissolved in 50 ml of isopropanol, 2.8 g of imidazole was added, and the mixture was heated under reflux for 10 hours. After evaporating the solvent, water was added, extracted with chloroform, and dried over anhydrous sodium sulfate. After evaporating the solvent, the obtained residue is subjected to silica gel column chromatography (elution solvent;
Dichloromethane: methanol = 16: 1) to give 1.33 g of 2-ethoxycarbonyl-3- (1-imidazolyl) methylquinoxaline as a yellow powder.

¹ H-NMR (CDCl ₃ ) δ ppm;
1.47 (3H, t, J = 7 Hz), 4.55 (2H,
q, J = 7 Hz), 5.82 (2H, s), 7.04
(2H, d, J = 5 Hz), 7.70 (1H, s),
7.8-8.0 (2H, m), 8.0-8.1 (1H,
m), 8.2-8.3 (1H, m).

Using the appropriate starting materials, the above-mentioned Reference Example 3,
In the same manner as in Nos. 9, 11 and 14, Nos. 1 to No. 70 compounds were obtained.

[0810]

[Table 1]

[0811]

[Table 2]

[0812]

[Table 3]

[0813]

[Table 4]

[0814]

[Table 5]

[0815]

[Table 6]

[0816]

[Table 7]

[0817]

[Table 8]

[0818]

[Table 9]

[0819]

[Table 10]

[0820]

[Table 11]

[0821]

[Table 12]

[0822]

[Table 13]

[0823]

[Table 14]

[0824]

[Table 15]

[0825]

[Table 16]

Using the appropriate starting materials, the above-mentioned Reference Examples 15 to
No. 21 shown in Tables 17 to 21 below in the same manner as No. 21. 1 to
No. 18 compounds were obtained.

[0827]

[Table 17]

[0828]

[Table 18]

[0829]

[Table 19]

[0830]

[Table 20]

[0831]

[Table 21]

Using the appropriate starting materials, the above-mentioned Reference Example 3,
In the same manner as in Nos. 9, 11, and 14, Nos. 1 to No. 126 compounds were obtained.

[0832]

[Table 22]

[0834]

[Table 23]

[0835]

[Table 24]

[0836]

[Table 25]

[0837]

[Table 26]

[0838]

[Table 27]

[0839]

[Table 28]

[0840]

[Table 29]

[0841]

[Table 30]

[0842]

[Table 31]

[0843]

[Table 32]

[0844]

[Table 33]

[0845]

[Table 34]

[0846]

[Table 35]

[0847]

[Table 36]

[0848]

[Table 37]

[0849]

[Table 38]

[0850]

[Table 39]

[0851]

[Table 40]

[0852]

[Table 41]

[0853]

[Table 42]

[0854]

[Table 43]

[0855]

[Table 44]

[0856]

[Table 45]

[0857]

[Table 46]

[0858]

[Table 47]

[0859]

[Table 48]

[0860]

[Table 49]

[0861]

[Table 50]

[0862]

[Table 51]

[0863]

[Table 52]

[0864]

[Table 53]

[0865]

[Table 54]

[0866]

[Table 55]

[0867]

[Table 56]

[0868]

[Table 57]

[0869]

[Table 58]

[0870]

[Table 59]

[0871]

[Table 60]

[0873]

[Table 61]

[0873]

[Table 62]

[0874]

[Table 63]

[0875] Using appropriate starting materials, the above-mentioned Reference Examples 15 to
No. 21 shown in Tables 64 to 65 below in the same manner as No. 21. 1 to
No. Compound 7 was obtained.

[0876]

[Table 64]

[0877]

[Table 65]

Using the appropriate starting materials, the above-mentioned Reference Example 3,
Compounds Nos. 1 to 26 below were obtained in the same manner as in Nos. 9, 11 and 14.

[0877]

[Table 66]

[0880]

[Table 67]

[0881]

[Table 68]

[0882]

[Table 69]

[0883]

[Table 70]

[0884]

[Table 71]

[0885]

[Table 72]

[0886]

[Table 73]

[0887]

[Table 74]

Using the appropriate starting materials, the above-mentioned Reference Examples 15 to
In the same manner as in No. 21, the following compounds Nos. 1 to 6 were obtained.

[0889]

[Table 75]

[0890]

[Table 76]

Example 1 Under a nitrogen atmosphere, 1.5 g of 2-ethoxycarbonyl-3-methylquinoxaline-4-oxide and 1.9 g of 3-aminomethylbenzofuran were mixed and stirred at 60 ° C. overnight. The reaction product was purified by silica gel chromatography (eluent; n-hexane: ethyl acetate = 3: 1), recrystallized from ethanol, and 1.3 g of 2 as colorless needles.
-[(3-benzofuranyl) methylaminocarbonyl]
-3-Methylquinoxaline-4-oxide was obtained. m.
p. 143-144 ° C.

Example 2 0.8 g of 2-carboxy-3-methylquinoxaline-4-oxide and 0.9 g of 2-aminomethyl-5-dimethylaminobenzofuran were added to 10 ml of dimethylformamide.
And 0.8 g of diethyl cyanophosphate and then 0.8 g of triethylamine were successively added dropwise under ice cooling. After stirring overnight at room temperature, the mixture was extracted with ethyl acetate, washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by silica gel chromatography (elution solvent: n-hexane: ethyl acetate = 1: 1), recrystallized from acetonitrile, and 0.6 g of 2-[(5 -Dimethylamino-2-benzofuranyl) methylaminocarbonyl] -3
-Methylquinoxaline-4-oxide was obtained. m. p.
155-157 ° C.

Example 3 0.5 g of 2-quinoxalinecarboxylic acid was dissolved in 10 ml of dichloromethane, and 0.7 g of dicyclohexylcarbodiimide was added. After stirring for 30 minutes, 0.5 g of 2-aminomethylbenzofuran was added and the mixture was stirred overnight. The insolubles were removed by filtration, and the organic layer was washed with saturated aqueous sodium hydrogen carbonate and water, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by silica gel chromatography (elution solvent: n-hexane: ethyl acetate = 3: 1), recrystallized from n-hexane-ethyl acetate, and 0.43 g as colorless scaly crystals. 2-
[(2-Benzofuranyl) methylaminocarbonyl] quinoxaline was obtained. m. p. 155-156 ° C.

Example 4 2-[(4-morpholinocarbonylmethoxybenzyl)
Aminocarbonyl] -3-methylquinoxaline 2.2 g
Was dissolved in 30 ml of methylene chloride, 1.3 g of m-chloroperbenzoic acid was added at room temperature, and the mixture was stirred for one day. Chloroform was added, and the organic layer was washed with an aqueous sodium thiosulfate solution, a saturated aqueous sodium hydrogen carbonate solution and water in that order, and dried over anhydrous sodium sulfate.
The solvent was distilled off, the residue was purified by silica gel chromatography (elution solvent: ethyl acetate), and recrystallized from acetonitrile to obtain 1.5 g of 2-[(4-
Morpholinocarbonylmethoxybenzyl) aminocarbonyl] -3-methylquinoxaline-4-oxide was obtained. m. p. 142-143 ° C.

[0895] The following Examples 28 to 103, 125, 126 and 12 were prepared in the same manner as in Example 4 using appropriate starting materials.
8, 130 to 135, 137, 138, 141, 143
146, 148, 150, 152, 154 to 157,
159, 161, 163, 165, 167, 169, 1
71, 173, 175, 177-184, 187-18
9, 191, 192, 194, 196-201, 203
To 205, 207, 209 to 213, 216, 219,
220, 224, 226, 228 to 230, 233, 2
35, 236, 239 and 240 and Example 43 described later
Compounds of 5-440, 442-479 and 484-487 were obtained.

Example 5 1.0 g of 2-cinnamylaminocarbonyl-3-methylquinoxaline was dissolved in 15 ml of dimethylformamide, and 160 mg of sodium hydride was added under ice cooling. After stirring at the same temperature for 30 minutes, 0.52 g of methyl iodide was added, and the mixture was stirred at room temperature for 2 hours. The mixture was poured into ice water, extracted with diethyl ether, washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by silica gel chromatography (elution solvent: n-hexane: ethyl acetate = 2: 1),
0.8 g of 2- (N-cinnamyl-N as a pale yellow liquid
-Methylaminocarbonyl) -3-methylquinoxaline was obtained.

[0897] _{^{1 H-NMR (CDCl 3)}} δppm;
2.78, 2.79 (3H, s), 2.92, 3.24
(3H, s), 3.98, 4.43 (2H, d, J = 6
Hz), 6.10-6.40 (1H, m), 6.40,
6.70 (1H, d, J = 16 Hz), 7.20-7.
50 (5H, m), 7.70-7.85 (2H, m),
8.00-8.15 (2H, m).

Using the appropriate starting materials, the following Examples 44, 66, 107, 110, 135,
138, 150, 151, 152, 153, 175, 1
76, 178, 186, 187, 191 and 192 were obtained.

Example 6 [0899] 0.4 g of 2-[(5-aminobenzofuran-2-yl) methylaminocarbonyl] -3-methylquinoxaline-4-oxide was suspended in 6 ml of pyridine, and stirred under ice-cooling with stirring for 0.1 ml of acetic anhydride. 26 g were added dropwise. After stirring at room temperature for one day, the mixture was poured into ice water, and the precipitated crystals were collected by filtration and washed with water. The crude crystals were recrystallized from acetonitrile to obtain 0.4 g of 2 as pale yellow needles.
-[(5-acetylaminobenzofuran-2-yl) methylaminocarbonyl] -3-methylquinoxaline-4
-An oxide was obtained. m. p. 183-184 ° C.

The following compounds of Examples 84 and 85 were obtained in the same manner as in Example 6 using appropriate starting materials.

Example 7 0.8 g of 2-[(5-aminobenzofuran-2-yl) methylaminocarbonyl] -3-methylquinoxaline-4-oxide was dissolved in 15 ml of dimethylformamide, and 0.5 g of potassium carbonate and N 0.37 g of -chloroacetylmorpholine was added, and the mixture was stirred at 70 ° C for 4 hours. The solvent was distilled off, water was added to the residue, chloroform was extracted,
After washing with water, it was dried over anhydrous sodium sulfate. The solvent is distilled off, and the residue is subjected to silica gel chromatography (elution solvent;
Ethyl acetate) and recrystallized from ethanol as oxalate to give 2-[(5-morpholinocarbonylmethylaminobenzofuran-2-yl) methylaminocarbonyl] -3-methylquinoxaline-4 as pale brown granular crystals. −
40 mg of the oxide were obtained. m. p. 159-167 ° C
(Disassembly).

[0902] _{^{1 H-NMR (CDCl 3)}} δppm;
3.09 (3H, s), 3.40-3.55 (2H,
m), 3.55-3.85 (6H, m), 3.90 (2
H, s), 4.78 (2H, d, J = 6 Hz), 6.6
0 (1H, s), 6.65 (1H, d, J = 7 Hz),
6.67 (1H, s), 7.28 (1H, d, J = 7H)
z), 7.75-7.85 (2H, m), 8.05-
8.15 (1H, m), 8.47 (1H, brs),
8.50-8.60 (1H, m).

Example 8 4.2 g of 2-[(5-ethoxycarbonylbenzofuran-2-yl) methylaminocarbonyl] -3-methylquinoxaline-4-oxide was added to 1.4 g of sodium hydroxide in 50 ml of methanol and 14 ml of water. Was added to the solution, and the mixture was stirred overnight at room temperature. The methanol was distilled off, water was added to the residue to make it acidic with hydrochloric acid, and the precipitated crystals were collected by filtration, washed with water and dried to give 2-[(5-carboxybenzofuran-2-yl) methylaminocarbonyl] -3- as a white powder. 3.8 g of methylquinoxaline-4-oxide were obtained. m.
p. 251-252 ° C (decomposition).

Example 9 2-[(6-methoxymethoxy-3-methylbenzofuran-2-yl) methylaminocarbonyl] -3-methylquinoxaline-4-oxide (2.1 g) was dissolved in tetrahydrofuran (20 ml) and methanol (20 ml). 10 ml of 6N hydrochloric acid was added, and the mixture was refluxed for 1 hour. The solvent was distilled off, the residue was extracted with chloroform, washed with saturated aqueous sodium hydrogen carbonate, water and saturated saline, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was recrystallized from dimethylformamide-water.
1.6 g of 2-[(6-hydroxy-) as yellow needles.
3-methylbenzofuran-2-yl) methylaminocarbonyl] -3-methylquinoxaline-4-oxide was obtained. m. p. 222-223 ° C (decomposition).

Example 10 2-[(4-hydroxy-3-methylbenzofuran-2)
-Yl) methylaminocarbonyl] -3-methylquinoxaline-4-oxide (0.55 g) was dissolved in dimethylformamide (4 ml), potassium carbonate (0.41 g) and methyl iodide (0.19 ml) were added, and the mixture was stirred at 60 ° C for 4 hours. Water was added, and the precipitated crystals were collected by filtration and washed with water. The crude crystals were treated with ethyl acetate
Recrystallization from n-hexane gave 0.41 g of 2-[(4-methoxy-3-methylbenzofuran-2-yl) methylaminocarbonyl] -3-methylquinoxaline-4-oxide as yellow prisms. . m. p. 19
6-197 ° C.

Example 11 2-[(Benzofuran-2-yl) methylaminocarbonyl] -3-methylquinoxaline-4-oxide 0.8
g was dissolved in 10 ml of chloroform, 0.47 g of N-bromosuccinimide was added, and the mixture was refluxed for 7 hours. The solvent was distilled off, and the residue was purified by silica gel chromatography (elution solvent: n-hexane: ethyl acetate = 2: 1),
Recrystallization from ethyl acetate-n-hexane gave 0.44 g of 2-[(3-bromobenzofuran-2) as colorless needles.
-Yl) methylaminocarbonyl] -3-methylquinoxaline-4-oxide was obtained. m. p. 170-171
° C.

The following Examples 31, 34, 38, 88, 93 and 9 were carried out in the same manner as in Example 11 using appropriate starting materials.
8, 119, 124, 125, 131 and 139 were obtained.

Example 12 2-[(4-methoxybenzyl) aminocarbonyl]-
10.5 g of 3-methylquinoxaline was dissolved in 150 ml of anhydrous methylene chloride, and 105 ml of a methylene chloride solution of boron tribromide (1M solution) was added dropwise under ice cooling. 2 at room temperature
After stirring for one day, the mixture was cooled, decomposed with methanol, and the solvent was distilled off. Water was added to the residue, and the mixture was neutralized with sodium hydrogen carbonate, and the precipitated crystals were collected by filtration, washed with water, and dried. Recrystallization from ethanol gave 10.0 g of 2-[(4-hydroxybenzyl) aminocarbonyl] -3-methylquinoxaline as colorless needles. m. p. 211-214 ° C.

Example 13 2-{[5- (1-acetoxyethyl) benzofuran-
2-yl] methylaminocarbonyl} -3-methylquinoxaline-4-oxide (4.5 g) in methanol (90 ml)
And 1.8 g of potassium carbonate was added thereto, followed by stirring overnight at room temperature. The solvent was distilled off, water was added to the residue, and the mixture was extracted with chloroform, washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off, and the crude crystals were recrystallized from ethyl acetate-n-hexane to give 3.4 g of 2-{[5- (1-hydroxyethyl) benzofuran-2-yl] methylaminocarbonyl} as colorless granular crystals. -3-Methylquinoxaline-4-oxide was obtained. m. p. 112-114 ° C.

Example 14 2-{[5- (1-hydroxyethyl) benzofuran-
2-yl] methylaminocarbonyl} -3-methylquinoxaline-4-oxide 0.8 g in chloroform 30m
and manganese dioxide (3.6 g) was added thereto, followed by refluxing for 6 hours. The reaction solution was filtered through celite and concentrated. The residue was recrystallized from ethyl acetate-n-hexane to give 0.5 g of 2-[(5-acetylbenzofuran-2-yl) as pale yellow granular crystals.
Yl) methylaminocarbonyl] -3-methylquinoxaline-4-oxide. m. p. 205-206
° C.

Example 15 0.7 g of 2-[(5-acetylbenzofuran-2-yl) methylaminocarbonyl] -3-methylquinoxaline-4-oxide was dissolved in 20 ml of anhydrous tetrahydrofuran, and methylmagnesium bromide was cooled under ice-cooling. 2.5 ml of a diethyl ether solution (1 M solution) was added dropwise. After stirring at room temperature for 3 hours, the mixture was poured into ice-ammonium chloride water, extracted with chloroform, washed with water and saturated saline, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was subjected to silica gel chromatography (elution solvent: n-hexane: ethyl acetate =
After purification by 1: 1), recrystallization from ethyl n-hexane monoacetate yielded 0.1 g of 2-g as pale yellow prisms.
{[5- (1-Hydroxy-1-methylethyl) benzofuran-2-yl] methylaminocarbonyl} -3-methylquinoxaline-4-oxide was obtained. m. p. 14
7-150 ° C.

Example 16 2-{[5- (5-tetrazolyl) benzofuran-2-
Yl] methylaminocarbonyl} -3-methylquinoxaline-4-oxide (1.4 g) in dimethylformamide 1
The mixture was dissolved in 5 ml, potassium carbonate 0.97 g and methyl iodide 0.44 g were added, and the mixture was stirred at room temperature for 4 hours. The reaction solution was poured into ice water, and the precipitated crystals were collected by filtration and recrystallized from dimethylformamide-ethanol to obtain 0.48 g of 2-{[5- (2-methyl-5-tetrazolyl) benzofuran-2- as a white powder. Yl] methylaminocarbonyl} -3-methylquinoxaline-4-oxide. m. p. 20
6-209 ° C.

Using the appropriate starting materials, the following compounds of Examples 36 and 161-164 were obtained in the same manner as in Example 16.

Example 17 3.65 g of 2-[(4-methoxycarbonylmethoxybenzyl) aminocarbonyl] -3-methylquinoxaline
Was dissolved in 50 ml of methanol, 6 ml of 2N sodium hydroxide was added, and the mixture was stirred at room temperature for 2 hours. Evaporate the solvent,
Water was added and the mixture was acidified with hydrochloric acid, and the precipitated crystals were collected by filtration, washed with water and dried to obtain 3.40 g of 2-[(4-carboxymethoxybenzyl) aminocarbonyl] -3-methylquinoxaline as a white powder.

¹ H-NMR (DMSO-d ₆ ) δpp
m; 2.83 (3H, s), 4.48 (2H, d, J =
6Hz), 4.66 (2H, s), 6.91 (2H,
d, J = 9 Hz), 7.33 (2H, d, J = 9H)
z), 7.8-8.0 (2H, m), 8.0-8.2
(2H, m), 9.33 (1H, t, J = 6 Hz).

[0916] The following Example 49 was obtained in the same manner as in Example 17 using appropriate starting materials.

Example 18 1.05 g of 2-[(4-carboxymethoxybenzyl) aminocarbonyl] -3-methylquinoxaline was dissolved in 10 ml of dimethylformamide, and 0.35 g of furfurylamine was added. .6
g and triethylamine 0.6 g were sequentially added dropwise. After stirring overnight at room temperature, the mixture was poured into ice water and the precipitated crystals were collected by filtration. Recrystallized from acetone-n-hexane to obtain 0.9 as a white powder.
2 g of 2-[(4-furfurylaminocarbonylmethoxybenzyl) aminocarbonyl] -3-methylquinoxaline were obtained. m. p. 175-176 ° C.

Example 19 2-[(4-methoxycarbonylmethoxybenzyl) aminocarbonyl] -3-methylquinoxaline 0.73 g
1.1 ml of 2-methoxyethylamine and toluene 1
It was dissolved in 0 ml and refluxed for 3 hours. The solvent was distilled off, and the residue was recrystallized from ethyl acetate to give 0.95 g of a white powder.
2-{[4- (2-methoxyethylaminocarbonylmethoxy) benzyl] aminocarbonyl} -3-methylquinoxaline. m. p. 138-140 ° C.

The following Examples 46, 47, 66, and 8 were prepared in the same manner as in Example 18 or 19, using appropriate starting materials.
2, 83, 109, 110, 127, 138, 146-
153, 157-159, 161-170, 173-1
75, 186, 187, 191-193, 195 and 1
96 compounds were obtained.

Example 20 2-[(4-hydroxybenzyl) aminocarbonyl]
1.8 g of -3-methylquinoxaline was dissolved in 30 ml of acetic acid and 150 ml of chloroform, a solution of 0.32 ml of bromine in acetic acid (5 ml) was added dropwise at room temperature, and the mixture was stirred at the same temperature for 3 hours. The reaction solution was washed with a saturated aqueous sodium hydrogen carbonate solution and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain 1.0 g of 2-[(3-bromo-4-hydroxybenzyl) aminocarbonyl] -3-methylquinoxaline as a yellow powder. This was reacted with N-chloroacetylmorpholine in the same manner as in Example 10 and then recrystallized from ethyl acetate-n-hexane to obtain 0.6 g of 2-colorless needles as 2-cylindrical crystals.
[(3-Bromo-4-morpholinocarbonylmethoxybenzyl) aminocarbonyl] -3-methylquinoxaline was obtained. m. p. 142-143 ° C.

Using the appropriate starting materials, the following Examples 45, 51, 56 and 58 were carried out in the same manner as in Example 10 or 20 above.
~ 60, 64-66, 78, 79, 82-83, 87,
106, 108, 110, 116, 117, 120, 1,
21, 123, 126, 127, 138, 140-14
2,144,146-153,156-164,167
177, 182, 185 to 193, 195, 196,
202, 207, 210-212, 222-224, 2
Compounds 30 to 234 and 241 were obtained.

Example 21 0.75 g of 2-[(4-methoxycarbonylbenzyl) aminocarbonyl] -3-methylquinoxaline was dissolved in 40 ml of tetrahydrofuran, and 0.17 g of lithium aluminum hydride was gradually added under ice-cooling and stirring. Was. After stirring at the same temperature for 3 hours, 10% aqueous sodium hydroxide solution 0.3m
After decomposing by adding l and water in order of 0.3 ml, the mixture was filtered through celite and dried over anhydrous sodium sulfate. The solvent is distilled off and 2
0.44 g of-[(4-hydroxymethylbenzyl) aminocarbonyl] -3-methylquinoxaline was obtained as a yellow powder.

[0923] _{^{1 H-NMR (CDCl 3)}} δppm;
1.75 (1H, t, J = 6 Hz), 4.70 (4H,
d, J = 6 Hz), 7.3-7.5 (4H, m), 7.
7-7.9 (2H, m), 8.0-8.1 (2H,
m), 8.39 (1H, brs).

Example 22 1.9 g of lithium aluminum hydride was suspended in 100 ml of tetrahydrofuran, and 2-[(4-methoxycarbonylmethoxybenzyl) aminocarbonyl] -3 was suspended under ice cooling.
-9.5 g of methylquinoxaline in tetrahydrofuran 5
0 ml solution was slowly added dropwise. After dropping, at the same temperature
The mixture was stirred for 0 minutes and then reacted at room temperature for 2 hours. After completion of the reaction, ethyl acetate was added under ice cooling, and then a saturated aqueous ammonium chloride solution was added. After filtering off the insolubles, the mixture was extracted with ethyl acetate and dried over anhydrous sodium sulfate. After evaporating the solvent, the residue was subjected to silica gel column chromatography (elution solvent; ethyl acetate: n-hexane = 1: 4) to give 2-{[4- (2-hydroxyethoxy) benzyl] aminocarbonyl} as a yellow liquid. 1.0 g of -3-methylquinoxaline was obtained.

[0925] _{^{1 H-NMR (CDCl 3)}} δppm;
2.25 (1H, br), 3.17 (3H, s),
9-4.1 (4H, m), 4.63 (2H, d, J = 6
Hz), 6.92 (2H, d, J = 7 Hz), 7.34
(2H, d, J = 7 Hz), 7.7-7.9 (2H, d, J = 7 Hz)
m), 8.0-8.1 (2H, m), 8.34 (1H,
br).

Example 23 2-{[4- (2-Hydroxyethoxy) benzyl] aminocarbonyl} -3-methylquinoxaline 0.2 g and triphenylphosphine 0.17 g were added to carbon tetrachloride 10
The resulting mixture was dissolved in ml and heated under reflux for 1.5 hours. After the reaction,
The solvent is distilled off, and the residue is subjected to silica gel column chromatography (elution solvent; ethyl acetate: n-hexane = 1: 2).
To give 0.10 g of 2-{[4- (2-chloroethoxy) benzyl] aminocarbonyl} -3-methylquinoxaline as a yellow liquid.

[0927] _{^{1 H-NMR (CDCl 3)}} δppm;
3.17 (3H, s), 3.82 (2H, t, J = 6H)
z), 4.24 (2H, t, J = 6 Hz), 4.64
(2H, d, J = 6 Hz), 6.93 (2H, d, J =
9 Hz), 7.35 (2H, d, J = 9 Hz), 7.7
-7.9 (2H, m), 8.0-8.1 (2H, m),
8.33 (1H, br).

Example 24 100 mg of 2-{[(4-chloroethoxy) benzyl] aminocarbonyl} -3-methylquinoxaline and 0.21 ml of morpholine were dissolved in 10 ml of dimethylformamide, and then 1.2 g of sodium iodide and potassium carbonate 300 mg was added and the mixture was heated at 60 ° C. for 7.5 hours. After completion of the reaction, the reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and saturated saline, and then dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was subjected to silica gel column chromatography (elution solvent: ethyl acetate: n-hexane =
2: 3) to give a yellow liquid. Then, it was dissolved in ethanol, an ethanol-hydrochloric acid solution was added, and the mixture was dried. The obtained crystals were recrystallized from ethanol-diethyl ether to obtain 70 mg of 2-{[4- (2-morpholinoethoxy) benzyl] aminocarbonyl} -3-methylquinoxaline hydrochloride as a yellow powder. m. p. 155-158 ° C
(Disassembly).

[0928] The compound of the following Example 203 was obtained in the same manner as in Example 24 using appropriate starting materials.

Example 25 2-{[4- (2-methyl-1,3-dioxolan-2)
-Yl) benzyl] aminocarbonyl} -3-methylquinoxaline-4-oxide (1.3 g) in acetone (20 ml)
And 10 ml of dichloromethane, 60 mg of p-toluenesulfonic acid was added, and the mixture was stirred at room temperature for 5 hours. The solvent was distilled off, the residue was extracted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate, dried over anhydrous sodium sulfate, and the solvent was distilled off.
The residue was recrystallized from ethanol to obtain 1.0 g of 2-[(4-acetylbenzyl) aminocarbonyl] -3-methylquinoxaline-4-oxide as pale yellow needles. m. p. 165-167 ° C.

Example 26 2.4 g of 2- [2- (4-methoxyphenylthio) ethylaminocarbonyl] -3-methylquinoxaline-4-oxide was dissolved in 40 ml of methylene chloride, and m-chloride was added under cooling with ice.
1.4 g of chloroperbenzoic acid was gradually added, and the mixture was stirred at the same temperature for 1 hour. The reaction solution was washed with an aqueous solution of sodium thiosulfate, a saturated aqueous solution of sodium bicarbonate and water, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by silica gel chromatography (elution solvent: ethyl acetate) and recrystallized from ethanol to obtain 1.8 g of 2- [2- (4
-Methoxyphenylsulfinyl) ethylaminocarbonyl] -3-methylquinoxaline-4-oxide. m. p. 156-157 ° C.

[0932] The compounds of the following Examples 212 and 217 to 220 were obtained in the same manner as in Example 26 using appropriate starting materials.

Example 27 2.4 g of 2- [2- (4-methoxyphenylthio) ethylaminocarbonyl] -3-methylquinoxaline-4-oxide was dissolved in 40 ml of methylene chloride, and m-chloride was added under ice cooling.
2.8 g of chloroperbenzoic acid was gradually added, and reacted at the same temperature for 1 hour. The reaction solution was washed with an aqueous solution of sodium thiosulfate, a saturated aqueous solution of sodium bicarbonate and water, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was recrystallized from ethanol to obtain 2.1 g of 2- [2- (4-methoxyphenylsulfonyl) ethylaminocarbonyl] -3-methylquinoxaline-4-oxide as colorless needles. Was. m. p. 14
8-150 ° C.

The following compounds of Examples 218 and 220 were obtained in the same manner as in Example 27 using appropriate starting materials.

Using the appropriate starting materials, the above Examples 1 and 2 were used.
Or in the same manner as in 3, compounds shown in the following Tables 77 to 135 were obtained.

[0936]

[Table 77]

[0937]

[Table 78]

[0938]

[Table 79]

[0939]

[Table 80]

[0940]

[Table 81]

[0941]

[Table 82]

[0942]

[Table 83]

[0943]

[Table 84]

[0944]

[Table 85]

[0945]

[Table 86]

[0946]

[Table 87]

[0947]

[Table 88]

[0948]

[Table 89]

[0949]

[Table 90]

[0950]

[Table 91]

[0951]

[Table 92]

[0952]

[Table 93]

[0953]

[Table 94]

[0954]

[Table 95]

[0955]

[Table 96]

[0956]

[Table 97]

[0957]

[Table 98]

[0958]

[Table 99]

[0959]

[Table 100]

[0960]

[Table 101]

[0961]

[Table 102]

[0962]

[Table 103]

[0963]

[Table 104]

[0964]

[Table 105]

[0965]

[Table 106]

[0969]

[Table 107]

[0967]

[Table 108]

[0968]

[Table 109]

[0969]

[Table 110]

[0970]

[Table 111]

[0971]

[Table 112]

[0972]

[Table 113]

[0973]

[Table 114]

[0974]

[Table 115]

[0975]

[Table 116]

[0976]

[Table 117]

[0977]

[Table 118]

[0978]

[Table 119]

[0979]

[Table 120]

[0980]

[Table 121]

[0981]

[Table 122]

[0982]

[Table 123]

[0983]

[Table 124]

[0984]

[Table 125]

[0985]

[Table 126]

[0986]

[Table 127]

[0987]

[Table 128]

[0988]

[Table 129]

[0989]

[Table 130]

[0990]

[Table 131]

[0991]

[Table 132]

[0992]

[Table 133]

[0993]

[Table 134]

[0994]

[Table 135]

[0995] Using appropriate starting materials, the above Examples 1 to 4
In the same manner as in the above, compounds shown in the following Tables 136 to 230 were obtained.

[0996]

[Table 136]

[0997]

[Table 137]

[0998]

[Table 138]

[0999]

[Table 139]

[1000]

[Table 140]

[1001]

[Table 141]

[1002]

[Table 142]

[1003]

[Table 143]

[1004]

[Table 144]

[1005]

[Table 145]

[1006]

[Table 146]

[1007]

[Table 147]

[1008]

[Table 148]

[1009]

[Table 149]

[1010]

[Table 150]

[1011]

[Table 151]

[1012]

[Table 152]

[1013]

[Table 153]

[1014]

[Table 154]

[1015]

[Table 155]

[1016]

[Table 156]

[1017]

[Table 157]

[1018]

[Table 158]

[1019]

[Table 159]

[1020]

[Table 160]

[1021]

[Table 161]

[1022]

[Table 162]

[1023]

[Table 163]

[1024]

[Table 164]

[1025]

[Table 165]

[1026]

[Table 166]

[1027]

[Table 167]

[1028]

[Table 168]

[1029]

[Table 169]

[1030]

[Table 170]

[1031]

[Table 171]

[1032]

[Table 172]

[1033]

[Table 173]

[1034]

[Table 174]

[1035]

[Table 175]

[1036]

[Table 176]

[1037]

[Table 177]

[1038]

[Table 178]

[1039]

[Table 179]

[1040]

[Table 180]

[1041]

[Table 181]

[1042]

[Table 182]

[1043]

[Table 183]

[1044]

[Table 184]

[1045]

[Table 185]

[1046]

[Table 186]

[1047]

[Table 187]

[1048]

[Table 188]

[1049]

[Table 189]

[1050]

[Table 190]

[1051]

[Table 191]

[1052]

[Table 192]

[1053]

[Table 193]

[1054]

[Table 194]

[1055]

[Table 195]

[1056]

[Table 196]

[1057]

[Table 197]

[1058]

[Table 198]

[1059]

[Table 199]

[1060]

[Table 200]

[1061]

[Table 201]

[1062]

[Table 202]

[1063]

[Table 203]

[1064]

[Table 204]

[1065]

[Table 205]

[1066]

[Table 206]

[1067]

[Table 207]

[1068]

[Table 208]

[1069]

[Table 209]

[1070]

[Table 210]

[1071]

[Table 211]

[1072]

[Table 212]

[1073]

[Table 213]

[1074]

[Table 214]

[1075]

[Table 215]

[1076]

[Table 216]

[1077]

[Table 217]

[1078]

[Table 218]

[1079]

[Table 219]

[1080]

[Table 220]

[1081]

[Table 221]

[1082]

[Table 222]

[1083]

[Table 223]

[1084]

[Table 224]

[1085]

[Table 225]

[1086]

[Table 226]

[1087]

[Table 227]

[1088]

[Table 228]

[1089]

[Table 229]

[1090]

[Table 230]

[1091]

[Table 231]

[1092]

[Table 232]

[1093]

[Table 233]

[1094]

[Table 234]

[1095]

[Table 235]

[1096]

[Table 236]

Using the appropriate starting materials, the above Examples 1 and 2 were used.
In the same manner as in Examples 3 and 3, compounds shown in Tables 237 to 259 below were obtained.

[1098]

[Table 237]

[1099]

[Table 238]

[1100]

[Table 239]

[1101]

[Table 240]

[1102]

[Table 241]

[1103]

[Table 242]

[1104]

[Table 243]

[1105]

[Table 244]

[1106]

[Table 245]

[1107]

[Table 246]

[1108]

[Table 247]

[1109]

[Table 248]

[1110]

[Table 249]

[1111]

[Table 250]

[1112]

[Table 251]

[1113]

[Table 252]

[1114]

[Table 253]

[1115]

[Table 254]

[1116]

[Table 255]

[1117]

[Table 256]

[1118]

[Table 257]

[1119]

[Table 258]

[1120]

[Table 259]

[1121]

[Table 260]

[1122]

[Table 261]

Example 480 2-{[3-methyl-3- (benzofuran-2-yl)]
-2-propenyl] aminocarbonyl} -3-methylquinoxaline-4-oxide (0.6 g) was treated with methylene chloride (40).
dissolved in 0.5 ml of 4-dimethylaminopyridine,
0.6 g of di-t-butyl-dicarbonate was added, and the mixture was stirred at room temperature for 1 day. The reaction solution was washed with dilute hydrochloric acid and saturated saline, and then dried over anhydrous sodium sulfate. The solvent is distilled off, and the residue is subjected to silica gel column chromatography (eluent: n
-Hexane: ethyl acetate = 3: 1) and recrystallized from n-hexane-diethyl ether to give 0.6 g of 2
-{Nt-butoxycarbonyl-N- [3-methyl-
3- (benzofuran-2-yl) -2-propenyl] aminocarbonyl} -3-methylquinoxaline-4-oxide was obtained.

[1124] m. p. 119-121 ° C, white powder.

Using the appropriate starting materials, the procedures of Examples 443, 444 and 451-453 were carried out in the same manner as in Example 480.
Was obtained.

Example 481 2-{[3-methyl-3- (benzofuran-2-yl)]
1.0 g of [-2-propenyl] aminocarbonyl} -3-methylquinoxaline-4-oxide was suspended in 50 ml of tetrahydrofuran, 180 mg of sodium hydride was added under a stream of argon, and the mixture was stirred at room temperature for 40 minutes. below freezing,
440 mg of ethyl chloroformate was added dropwise, and the mixture was stirred at room temperature overnight. The reaction solution was poured into ice water, extracted with dichloromethane, washed with water and saturated saline, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the obtained residue was purified by silica gel column chromatography (eluent: methylene chloride: methanol = 400: 1), and recrystallized from diethyl ether to give 0.77 g of 2- ｛N-ethoxycarbonyl. -N- [3-methyl-3- (benzofuran-2-yl)
2-propenyl] aminocarbonyl} -3-methylquinoxaline-4-oxide was obtained.

[1127] m. p. 124-125 ° C, pale yellow granules.

The compounds of Examples 443, 444451, 452 and 454 were obtained in the same manner as in Example 481, using appropriate starting materials.

Example 482 2-{[3-methyl-3- (benzofuran-2-yl)]
1.0 g of -2-propenyl] aminocarbonyl} -3-methylquinoxaline-4-oxide was suspended in 10 ml of dimethylformamide, and sodium hydride 18
0 ml was added, and the mixture was stirred at room temperature for 15 minutes. 320 mg of methoxymethyl chloride was added dropwise under ice cooling, and the mixture was stirred overnight at room temperature. The reaction mixture was poured into ice water, extracted with ethyl acetate, washed with water and saturated saline, and dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvent was purified by silica gel column chromatography (eluent; n-hexane: ethyl acetate = 4: 1) and recrystallized from diethyl ether to give 0.23 g of 2-ΔN -Methoxymethyl-N- [3-
Methyl-3- (benzofuran-2-yl) -2-propenyl] aminocarbonyl {-3-methylquinoxaline-
The 4-oxide was obtained as a mixture of rotamers.

[1130] m. p. 122-124 ° C, pale yellow powder ¹ H-NMR (CDCl ₃ ) δ ppm; 1.70, 2.
20 (3H, s), 2.66 (3H, s), 3.22,
3.55 (3H, s), 4.19, 4.58 (2H,
d, J = 7 Hz), 4.68, 5.12 (2H, s),
6.43, 6.51 (1H, t, J = 7 Hz), 6.5
5, 6.70 (1H, s), 7.13 to 7.30 (2
H, m), 7.40-7.60 (2H, m), 7.70
7.85 (2H, m), 8.10 (1H, m), 8.
60 (1H, m).

Using suitable starting materials, the same procedures as in Example 482 were repeated except that the above Examples 443, 444, 451 to 455,
457 and 479 compounds were obtained.

Example 483 92 mg of sodium hydride in dimethylformamide 20
2-{[3-methyl-3- (benzofuran-2-yl) -2-propenyl] aminocarbonyl}-
746 mg of 3-methylquinoxaline-4-oxide was added, and the mixture was stirred at room temperature for 30 minutes. Chloromethyl pivalate 3
32 μl and a catalytic amount of tetra-n-butylammonium iodide were added and stirred for 1 hour. The reaction mixture was poured into water and extracted with ethyl acetate. After washing with water and a saturated saline solution, it was dried. After evaporating the solvent, the obtained residue was purified by silica gel column chromatography, and then diethyl ether-n
-Recrystallized from hexane to obtain 300 mg of 2- {N-pivaloyloxymethyl-N- {3-methyl-3- (benzofuran-2-yl) -2-propenyl] aminocarbonyl} -3-methylquinoxaline- The 4-oxide was obtained as a mixture of rotamers.

[1133] m. p. 127-129 ° C, pale yellow needles ¹ H-NMR (CDCl ₃ ) δ ppm;
29 (9H, s), 1.66, 2.20 (3H, br
s), 2.62, 2.66 (3H, s), 4.28,
4.59 (2H, d, J = 7.2 Hz), 5.45,
5.73 (2H, s), 6.38, 6.52 (1H,
t, J = 7.2 Hz), 6.57, 6.71 (1H,
s), 7.15-7.35 (2H, m), 7.4-7.
5 (1H, m), 7.5-7.6 (1H, m), 7.7
6-7.87 (2H, m), 8.05-8.15 (1
H, m), 8.55-7.65 (1H, m).

Using the appropriate starting materials, the procedures described in Examples 443, 451 to 457 and 479 were carried out in the same manner as in Example 483.
Was obtained.

Using the appropriate starting materials, the above Examples 1-4
In the same manner as in the above, compounds shown in the following Tables 262 to 264 were obtained.

[1136]

[Table 262]

[1137]

[Table 263]

[1138]

[Table 264]

[1139] Pharmacological test method Sugar uptake test using L6 cells L6 cells (derived from rat striated muscle) were subjected to MEM / 10% FCS.
(Calf serum) and 4x
10 ⁴ cells are seeded and cultured under 2% FCS to differentiate into muscle cells. The test compound was added on the sixth day. After removing the culture solution on the 7th day, [ ³ H] -2-deoxyglucose was added and reacted at 37 ° C. for 10 minutes. After the reaction, the cells were washed twice with cold phosphate buffered saline, the cells were lysed with 0.1% sodium dodecyl sulfate, and the radioactivity was measured.
The sugar uptake% was expressed as the radioactivity% when the test compound was added, with the control being 100%. The results are shown in Tables 265 and 266 below.

[1140]

[Table 265]

[1141]

[Table 266]

 ──────────────────────────────────────────────────続 き Continuing on the front page (72) Inventor Masahito Miyake 1 Kamiyashiki, Kitamura, Kitajima-cho, Itano-gun, Tokushima Prefecture Masters L.Kitajima Building No. 17, Building No. 102 39-8 Nakase Nishinokoshi 8 (72) Inventor Hidehiro Yoshida 304-4 Hashimoto-cho, Tokushima City, Tokushima Prefecture (72) Inventor Atsunori Ueyama 4-46 Kita Sako Ichibancho, Tokushima City, Tokushima Prefecture No. 403, Sako (72) Inventor Takao Nishi, 28, Taro, Yasu, No. 2, Taro, Kitajima-cho, Itano-gun, Tokushima Pref. PHARM. BULL. , (1967), 15-7! , Pp. 1079-1082. CHEM. ENG. DATE, (1984), 29, P229-231 HETEROCYCLES, (1987), 26-3! , P699-711

Claims (6)

(57) [Claims] 1. A compound of the general formula Wherein R ¹ represents a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, an amino group which may have a lower alkyl group as a substituent, or an aminocarbonyl group which may have a lower alkyl group as a substituent. . R
² represents a hydrogen atom, a lower alkyl group which may have a halogen atom as a substituent, a phenyl group, a morpholino-substituted lower alkyl group or an imidazolyl-substituted lower alkyl group. n represents 0. m represents 0 or 1. r is 1 or 2
Is shown. R ³ and R ⁴ are the same or different,
a) hydrogen atom; b) lower alkyl group; c) phenyl lower alkoxycarbonyl group; d) lower alkanoyloxy-substituted lower alkyl group; e) lower alkanoyl group; f) lower alkoxycarbonyl group; g) lower alkoxy lower alkyl group; h) phenoxycarbonyl group; i) lower alkanoyl group-substituted lower alkyl group; j) lower alkoxycarbonyloxy-substituted lower alkyl group; k) benzoyl-substituted lower alkyl group which may have a halogen atom as a substituent on the phenyl ring; ) Group -E- NR ⁵² R ⁵³ (R
⁵² and R ⁵³ are the same or different and represent a hydrogen atom, a lower alkyl group, a lower alkoxycarbonyl group or a phenyl group. R ⁵² and R ⁵³ may be bonded to each other with or without another nitrogen atom or oxygen atom together with the nitrogen atom to which they are bonded to form a 5- or 6-membered saturated heterocyclic ring. E represents a lower alkylene group, a group -C (= O)-or a group -C (= O) -A- (A is a lower alkylene group). ); M) group (Wherein A is the same as described above; R ⁵⁴ represents a hydrogen atom or a lower alkyl group.); N) group embedded image (Wherein A represents a lower alkylene group; p represents an integer of 1 to 3; R ⁵ is a lower alkoxy-substituted lower alkoxy group;
A lower alkoxy group, an amino group that may have a lower alkyl group as a substituent, a halogen atom, a nitro group, a hydroxyl group, a lower alkyl group that may have a hydroxyl group as a substituent, a lower alkenyloxy group, a carboxy-substituted lower alkoxy group, A lower alkoxycarbonyl-substituted lower alkoxy group, a lower alkoxycarbonyl group, a halogen atom-substituted lower alkoxy group, a hydroxyl-substituted lower alkoxy group, and a group selected from the group consisting of a lower alkyl group and a lower alkoxy group as a substituent on a phenyl ring; A phenyl lower alkoxy group, a 1,3-dioxolanyl group which may have a lower alkyl group as a substituent, a lower alkanoyl group, a morpholino-substituted lower alkoxy group, a morpholino-substituted lower alkyl group, a morpholinocarbonyl group, or a group -Y- A ₁ - ONR ⁶ R ⁷ (wherein A ₁ is a lower alkylene group, Y represents a -NH- group -O- or a group .R
⁶ and R ⁷ are the same or different and are a hydrogen atom, a lower alkyl group which may have a hydroxyl group as a substituent, a phenyl lower alkyl group which may have a lower alkoxy group as a substituent on a phenyl ring, a furyl-substituted lower alkyl group And a lower alkoxy-substituted lower alkyl group. Also R
⁶ and R ⁷ may form a 5- or 6-membered saturated heterocyclic ring with or without a nitrogen atom or an oxygen atom together with the nitrogen atom to which they are bonded. The heterocycle includes:
It may have 1 to 3 groups selected from the group consisting of a hydroxyl group, a lower alkyl group and a phenyl lower alkyl group as a substituent. ). O) an amino group or a lower alkoxy-substituted lower group which may have on the phenyl ring a lower alkoxy group or a halogen atom as a substituent, and a group selected from the group consisting of a lower alkanoyl group and a phenyl lower alkenylcarbonyl group as a substituent. An alkoxy group, a tetrazolyl group which may have a lower alkyl group as a substituent on the tetrazole ring, a hydroxyl group, a group -OA ₄ -CO-NR ⁴⁰ R ⁴¹
(A ₄ represents a lower alkylene group; R ⁴⁰ and R ⁴¹ are the same or different and represent a hydrogen atom or a lower alkyl group; and R ⁴⁰ and R ⁴¹ are, together with the nitrogen atom to which they are bonded, another nitrogen atom or oxygen. A 5- or 6-membered saturated heterocyclic ring may be formed by bonding to each other with or without an atom;), a lower alkenyloxy group, a nitro group and a lower alkyl group which may have a halogen atom as a substituent. A phenyl lower alkenyl group which may have a group selected from the group consisting of: p) an alkenyl group; q) a cycloalkyl lower alkyl group; r) a naphthyl lower alkyl group; s) a lower alkoxy group as a substituent on the phenyl ring. A phenylthio-substituted lower alkyl group which may have; t) a phenylsulfinyl which may have a lower alkoxy group as a substituent on the phenyl ring; A substituted lower alkyl group; u) a phenylsulfonyl-substituted lower alkyl group which may have a lower alkoxy group as a substituent on the phenyl ring; v)
A phenoxy-substituted lower alkyl group; w) group (In the formula, q represents an integer of 1 to 3. Is a 5- to 14-membered monocyclic, dimeric or ternary saturated or unsaturated heterocyclic-substituted lower alkyl having 1-4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur Represents a group. R ⁸ is substituted on the above heterocyclic ring, and R ⁸ is
Hydrogen atom, oxo group, lower alkyl group which may have a hydroxyl group as a substituent, halogen atom, nitro group, lower alkoxy group, cyano group, lower alkoxycarbonyl group, having a lower alkanoyl group as a substituent on a phenyl ring A phenyl lower alkoxy group which may have an amino group, a carboxy-substituted lower alkoxy group,
Carboxy group, lower alkoxycarbonyl-substituted lower alkoxy group, hydroxyl group, lower alkoxy-substituted lower alkoxy group, lower alkenyloxy group, lower alkanoyloxy-substituted lower alkyl group, halogen atom-substituted lower alkyl group, lower alkanoyl group, substituent on phenyl ring A lower alkyl group, a lower alkoxy-substituted lower alkoxy group, a hydroxyl group, a phenyl group which may have a group selected from the group consisting of a halogen atom and a lower alkoxy group, a lower alkenyl group, a morpholinocarbonyl lower alkoxy group,
A lower alkylsulfinyl group, an amino group-substituted lower alkyl group which may have a group selected from the group consisting of a lower alkylsulfonyl group and a lower alkanoyl group as a substituent, a lower alkylthio group, a lower alkylsulfonyl group,
A lower alkanoyloxy group, a 1,3-dioxolanyl-substituted lower alkyl group which may have a lower alkyl group as a substituent, a lower alkanoyl group-substituted lower alkyl group,
Aminocarbonyl-substituted lower alkyl groups which may have lower alkyl groups as substituents, lower alkoxycarbonyl group-substituted lower alkenyl groups, aminocarbonyl-substituted lower alkenyl groups which may have lower alkyl groups as substituents, carboxy-substituted lower alkenyl Group, benzoyl group, lower alkoxy lower alkyl group, group (In the formula, s represents an integer of 1 to 3. Represents a 5- or 6-membered saturated or unsaturated heterocyclic group having 1 to 4 hetero atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom. R ⁴⁵ is substituted on the above heterocyclic ring;
⁴⁵ represents a hydrogen atom, a lower alkyl group, a lower alkoxy lower alkyl group, a phenyl group or an oxo group. ), Group (In the formula, t represents an integer of 1 to 3. Represents a 5- to 6-membered saturated or unsaturated heterocyclic-substituted lower alkyl group having 1 to 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom. R ⁴⁶ is substituted on the above heterocyclic ring, and R ⁴⁶ represents a hydrogen atom, a lower alkyl group or an oxo group. ) Or a group — (C ＝ O) 1NR ⁹ R ¹⁰
(Where l represents 0 or 1. R ⁹ and R ¹⁰ are the same or different and are each a hydrogen atom, a lower alkanoyl group, a lower alkyl group, a morpholinocarbonyl lower alkyl group, a cycloalkylcarbonyl group, a phenyl lower alkenylcarbonyl group, A lower alkylsulfonyl group, an aminocarbonyl group which may have a lower alkyl group as a substituent, a phenylsulfonyl group which may have a lower alkyl group as a substituent on a phenyl ring, a phenyl lower alkenyl group, a substituent on a phenyl ring A halogen atom, a lower alkoxy group, a benzoyl group which may have 1 to 3 groups selected from the group consisting of an amino group and a hydroxyl group which may have a lower alkanoyl group as a substituent, and a lower alkanoyl group which has a substituent Amino-substituted lower alkanoyl group, Amino substituted sulfonyl group which may have lower alkyl group as a substituent, a phenyl lower alkyl group, an amino group which may have a lower alkanoyl group as a phenyl group or a substituted group. The R ⁹ and R ^10, these May form a 5- or 6-membered saturated heterocyclic ring with or without another nitrogen atom or oxygen atom together with the nitrogen atom to which is bonded.
Is shown. ); X) group _{^{-A 5 -CR 42 R 43 R 44}} ( wherein A ₅
Represents a lower alkylene group. R ⁴² and R ⁴³ together form a group = O, a group = N-OH or a lower alkylenedioxy group. R ⁴⁴ represents a phenyl group which may have a lower alkoxy group as a substituent on the phenyl ring. Y) a 2,3-dihydro-1H-indenyl ring having a group selected from the group consisting of an oxo group, a hydroxyl group and a silyloxy group having a lower alkyl group as a substituent on the 2,3-dihydro-1H-indenyl ring; Dihydro-1H-indenyl-substituted lower alkyl group; or z) group Wherein u represents an integer of 1 to 3. Is a 5- to 14-membered mono-, di- or tri-cyclic saturated or unsaturated heterocyclic-substituted lower alkenyl group having 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur Is shown. R ⁴⁷ is substituted on the heterocyclic ring, and R ⁴⁷ is a hydrogen atom, a halogen atom-substituted lower alkyl group, an oxo group, a halogen atom, a lower alkoxy group, a lower alkyl group, a lower alkoxycarbonyl group, a carboxy group, or a lower substituent. It may have an aminocarbonyl group which may have an alkyl group, an amino group which may have a lower alkanoyl group as a substituent, or a group selected from a lower alkoxy group and a halogen atom as a substituent on a phenyl ring. Phenyl group or group (Wherein A ₆ , R ⁴⁵ and s are the same as described above). ). A) R ³ and R ⁴ may be bonded together with the nitrogen atom to which they are bonded to form a 1,2,3,4-tetrahydroisoquinolyl group. The heterocyclic ring may have a lower alkoxy group as a substituent. Where R ¹
Represents a hydrogen atom, R ² represents a methyl group, R ³ represents a hydrogen atom,
When m represents 0, R ⁴ is a 2- (imidazolyl-2-yl) ethyl group, 2- (imidazolyl-4-yl) ethyl
Group, 2- (indolyl-3-yl) ethyl group or sec
It must not be a -butyl group. R ¹ is a hydrogen source
Child, R ² represents a phenyl group, and when m represents 1, R ³
And R ⁴ must not both be hydrogen atoms. Further, R
¹ represents a hydrogen atom, R ² represents a phenyl group, and m represents 0
In this case, R ³ and R ⁴ are the same or different and each represent a hydrogen atom or
It must not be a lower alkyl group. ] The quinoxaline derivative represented by these, or its salt. 2. A compound of the general formula Wherein R ¹ represents a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, an amino group which may have a lower alkyl group as a substituent, or an aminocarbonyl group which may have a lower alkyl group as a substituent. . R
² represents a hydrogen atom, a lower alkyl group which may have a halogen atom as a substituent, a phenyl group, a morpholino-substituted lower alkyl group or an imidazolyl-substituted lower alkyl group. n and m each represent 0 or 1. r is 1 or 2
Is shown. R ³ and R ⁴ are the same or different,
a) hydrogen atom; b) lower alkyl group; c) phenyl lower alkoxycarbonyl group; d) lower alkanoyloxy-substituted lower alkyl group; e) lower alkanoyl group; f) lower alkoxycarbonyl group; g) lower alkoxy lower alkyl group; h) phenoxycarbonyl group; i) lower alkanoyl group-substituted lower alkyl group; j) lower alkoxycarbonyloxy-substituted lower alkyl group; k) benzoyl-substituted lower alkyl group which may have a halogen atom as a substituent on the phenyl ring; ) Group -ER ⁵² R ⁵³ (R ⁵²
And R ⁵³ are the same or different and represent a hydrogen atom, a lower alkyl group, a lower alkoxycarbonyl group or a phenyl group. R ⁵² and R ⁵³ may be bonded to each other with or without another nitrogen atom or oxygen atom together with the nitrogen atom to which they are bonded to form a 5- or 6-membered saturated heterocyclic ring. E represents a lower alkylene group, a group -C (= O)-or a group -C (= O) -A- (A is a lower alkylene group). ); M) group (Wherein A is the same as described above; R ⁵⁴ represents a hydrogen atom or a lower alkyl group); n) group embedded image (Wherein A represents a lower alkylene group; p represents an integer of 1 to 3; R ⁵ is a hydrogen atom, a lower alkoxy-substituted lower alkoxy group, a lower alkoxy group, or an amino which may have a lower alkyl group as a substituent; Group, halogen atom, nitro group, hydroxyl group, lower alkyl group which may have a hydroxyl group as a substituent, lower alkenyloxy group, carboxy-substituted lower alkoxy group, lower alkoxycarbonyl-substituted lower alkoxy group, lower alkoxycarbonyl group, halogen atom substitution A lower alkoxy group, a hydroxyl-substituted lower alkoxy group, a phenyl lower alkoxy group which may have a group selected from the group consisting of a lower alkyl group and a lower alkoxy group as a substituent on a phenyl ring, having a lower alkyl group as a substituent 1,3-dioxolanyl group, lower alkanoy Group, a morpholino-substituted lower alkoxy group, a morpholino-substituted lower alkyl group, a morpholinocarbonyl group or a group _{^{-Y-A 1 -CONR 6 R 7}} ( wherein A ₁ is a lower alkylene group, Y is a group -O- or a group -NH −
Is shown. R ⁶ and R ⁷ are the same or different and are each a hydrogen atom,
A lower alkyl group which may have a hydroxyl group as a substituent, a phenyl lower alkyl group which may have a lower alkoxy group as a substituent on a phenyl ring, a furyl-substituted lower alkyl group or a lower alkoxy-substituted lower alkyl group are shown. R ⁶ and R ⁷ may form a 5- or 6-membered saturated heterocyclic ring with or without a nitrogen atom or an oxygen atom together with the nitrogen atom to which they are bonded. In the heterocyclic ring, a group selected from the group consisting of a hydroxyl group, a lower alkyl group and a phenyl lower alkyl group as a substituent is 1 to 3;
You may have one. ). O) an amino group or a lower alkoxy-substituted lower group which may have on the phenyl ring a lower alkoxy group or a halogen atom as a substituent, and a group selected from the group consisting of a lower alkanoyl group and a phenyl lower alkenylcarbonyl group as a substituent. An alkoxy group, a tetrazolyl group which may have a lower alkyl group as a substituent on the tetrazole ring, a hydroxyl group, a group -OA ₄ -CO
-NR ⁴⁰ R ⁴¹ (A ₄ is .R ⁴⁰ and R ⁴¹ represents a lower alkylene group is a hydrogen atom or a lower alkyl group the same or different. The R ⁴⁰ and R ⁴¹ are other together with the nitrogen atom to which they are attached May form a 5- or 6-membered saturated heterocyclic ring via a nitrogen atom or an oxygen atom with or without intervening.), A lower alkenyloxy group, a nitro group and a halogen atom as a substituent A phenyl lower alkenyl group which may have a group selected from the group consisting of: a) a alkenyl group; q) a cycloalkyl lower alkyl group; r) a naphthyl lower alkyl group; s) a substituent on the phenyl ring A phenylthio-substituted lower alkyl group which may have a lower alkoxy group as a substituent; t) a phenyl group which may have a lower alkoxy group as a substituent on a phenyl ring; Sulfinyl-substituted lower alkyl group; u) phenylsulfonyl-substituted lower alkyl group which may have a lower alkoxy group as a substituent on the phenyl ring; v) phenoxy-substituted lower alkyl group; w) based embedded image (In the formula, q represents an integer of 1 to 3. Is a 5- to 14-membered monocyclic, dimeric or ternary saturated or unsaturated heterocyclic-substituted lower alkyl having 1-4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur Represents a group. R ⁸ is substituted on the above heterocyclic ring, and R ⁸ is
Hydrogen atom, oxo group, lower alkyl group which may have a hydroxyl group as a substituent, halogen atom, nitro group, lower alkoxy group, cyano group, lower alkoxycarbonyl group, having a lower alkanoyl group as a substituent on a phenyl ring A phenyl lower alkoxy group which may have an amino group, a carboxy-substituted lower alkoxy group,
Carboxy group, lower alkoxycarbonyl-substituted lower alkoxy group, hydroxyl group, lower alkoxy-substituted lower alkoxy group, lower alkenyloxy group, lower alkanoyloxy-substituted lower alkyl group, halogen atom-substituted lower alkyl group, lower alkanoyl group, substituent on phenyl ring A lower alkyl group, a lower alkoxy-substituted lower alkoxy group, a hydroxyl group, a phenyl group which may have a group selected from the group consisting of a halogen atom and a lower alkoxy group, a lower alkenyl group, a morpholinocarbonyl lower alkoxy group,
A lower alkylsulfinyl group, an amino group-substituted lower alkyl group which may have a group selected from the group consisting of a lower alkylsulfonyl group and a lower alkanoyl group as a substituent, a lower alkylthio group, a lower alkylsulfonyl group,
A lower alkanoyloxy group, a 1,3-dioxolanyl-substituted lower alkyl group which may have a lower alkyl group as a substituent, a lower alkanoyl group-substituted lower alkyl group,
Aminocarbonyl-substituted lower alkyl groups which may have lower alkyl groups as substituents, lower alkoxycarbonyl group-substituted lower alkenyl groups, aminocarbonyl-substituted lower alkenyl groups which may have lower alkyl groups as substituents, carboxy-substituted lower alkenyl Group, benzoyl group, lower alkoxy lower alkyl group, group (In the formula, s represents an integer of 1 to 3. Represents a 5- or 6-membered saturated or unsaturated heterocyclic group having 1 to 4 hetero atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom. R ⁴⁵ is substituted on the above heterocyclic ring;
⁴⁵ represents a hydrogen atom, a lower alkyl group, a lower alkoxy lower alkyl group, a phenyl group or an oxo group. ), Group (Wherein t represents an integer of 1 to 3. Represents a 5- to 6-membered saturated or unsaturated heterocyclic-substituted lower alkyl group having 1 to 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom. R ⁴⁶ is substituted on the above heterocyclic ring, and R ⁴⁶ represents a hydrogen atom, a lower alkyl group or an oxo group. ) Or a group — (C ＝ O) 1NR ⁹ R ¹⁰
(Where l represents 0 or 1. R ⁹ and R ¹⁰ are the same or different and are each a hydrogen atom, a lower alkanoyl group, a lower alkyl group, a morpholinocarbonyl lower alkyl group, a cycloalkylcarbonyl group, a phenyl lower alkenylcarbonyl group, A lower alkylsulfonyl group, an aminocarbonyl group which may have a lower alkyl group as a substituent, a phenylsulfonyl group which may have a lower alkyl group as a substituent on a phenyl ring, a phenyl lower alkenyl group, a substituent on a phenyl ring A halogen atom, a lower alkoxy group, a benzoyl group which may have 1 to 3 groups selected from the group consisting of an amino group and a hydroxyl group which may have a lower alkanoyl group as a substituent, and a lower alkanoyl group which has a substituent Amino-substituted lower alkanoyl group, Amino substituted sulfonyl group which may have lower alkyl group as a substituent, a phenyl lower alkyl group, an amino group which may have a lower alkanoyl group as a phenyl group or a substituted group. The R ⁹ and R ^10, these May form a 5- or 6-membered saturated heterocyclic ring with or without another nitrogen atom or oxygen atom together with the nitrogen atom to which is bonded.
Is shown. ); X) group _{^{-A 5 -CR 42 R 43 R 44}} ( wherein A ₅
Represents a lower alkylene group. R ⁴² and R ⁴³ together form a group = O, a group = N-OH or a lower alkylenedioxy group. R ⁴⁴ represents a phenyl group which may have a lower alkoxy group as a substituent on the phenyl ring. Y) a 2,3-dihydro-1H-indenyl ring having a group selected from the group consisting of an oxo group, a hydroxyl group and a silyloxy group having a lower alkyl group as a substituent on the 2,3-dihydro-1H-indenyl ring; Dihydro-1H-indenyl-substituted lower alkyl group; or z) group (In the formula, u represents an integer of 1 to 3. Is a 5- to 14-membered mono-, di- or tri-cyclic saturated or unsaturated heterocyclic-substituted lower alkenyl group having 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur Is shown. R ⁴⁷ is substituted on the heterocyclic ring, and R ⁴⁷ is a hydrogen atom, a halogen atom-substituted lower alkyl group, an oxo group, a halogen atom, a lower alkoxy group, a lower alkyl group, a lower alkoxycarbonyl group, a carboxy group, or a lower substituent. It may have an aminocarbonyl group which may have an alkyl group, an amino group which may have a lower alkanoyl group as a substituent, or a group selected from a lower alkoxy group and a halogen atom as a substituent on a phenyl ring. Phenyl group or group (Wherein A ₆ , R ⁴⁵ and s are the same as described above). ). A) R ³ and R ⁴ may be bonded together with the nitrogen atom to which they are bonded to form a 1,2,3,4-tetrahydroisoquinolyl group. The heterocyclic ring may have a lower alkoxy group as a substituent. ] An antidiabetic agent comprising, as an active ingredient, at least one compound selected from quinoxaline derivatives represented by the following formulas and salts thereof. 3. 2-[(3-methyl-7-trifluoro
Methylbenzofuran-2-yl) methylaminocarboni
3-Methylquinoxaline-4-oxide. 4. 2-[(2-phenyl-5-methyloxy)
Sazol-4-yl) methylaminocarbonyl] -3-
Methylquinoxaline-4-oxide. 5. The compound according to claim 3 as an active ingredient.
A therapeutic agent for diabetes. 6. The compound according to claim 4 as an active ingredient.
A therapeutic agent for diabetes.