JPH0812579A - Diabetes mellitus-treating agent - Google Patents

Abstract

PURPOSE:To obtain a diabetes mellitus treating agent containing a novel quinoxaline derivative not acting on insulin secretion and sugar release in liver and having hypoglycemic action which is not drastic and useful as a treating medicine for diabetes mellitus and various diabetic complications, etc. CONSTITUTION:A quinoxaline deriivative is expressed by formula I [R<1> is H, a halogen, a lower alkyl, a lower alkoxy, etc.; R<2> is H, a (halogen-substituted) lower alkyl, phenyl, a morpholino-substituted lower alkyl, etc.; (n) is 0; (m) is 0 or 1; (r) is 1 or 2; R<3> and R<4> are each H, a lower alkyl, a phenyl-lower alkyl alkoxycarbonyl, a lower alkanoyloxy-substituted lower alkyl, etc., with the proviso that when R<1> is H, R<2> is methyl, R<3> is H and (m) is 0, R<4> is not 2-(imidazolyl-2-yl)ethyl, sec-butyl, etc.] or its salt, e.g. 2-[(3-benzofuranyl) methylaminocarbonyl]-3-methylquinoxaline-4-oxide. The compound of formula I is obtained by reacting, e.g. a compound of formula I with a compound of formula III.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD 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]

[Chemical 25]

[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] Indicates 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
Indicates 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) a 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; l) group -ER
⁵² R ⁵³ (R ⁵² and R ⁵³ are the same or different and each is a hydrogen atom,
A lower alkyl group, a lower alkoxycarbonyl group or a phenyl group is shown. R ⁵² and R ⁵³ may be bonded to each other together with the nitrogen atom to which they are bonded via another nitrogen atom or an oxygen atom to form a 5- or 6-membered saturated heterocycle. E is a lower alkylene group, group -C
(= O)-or a group -C (= O) -A- (A is a lower alkylene group). ); M) group

[0005]

[Chemical formula 26]

(In the formula, A is the same as above. R ⁵⁴ represents a hydrogen atom or a lower alkyl group.); N) group

[0007]

[Chemical 27]

(In the formula, 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, Halogen atom-substituted lower alkoxy group, hydroxyl group-substituted lower alkoxy group, phenyl lower alkoxy group which may have a group selected from the group consisting of lower alkyl group and lower alkoxy group on the phenyl ring, lower alkyl group as 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 (wherein 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 each is a hydrogen atom or 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,
A furyl-substituted lower alkyl group or a lower alkoxy-substituted lower alkyl group is shown. R ⁶ and R ⁷ together with the nitrogen atom to which they are bonded may form a 5- or 6-membered saturated heterocycle with or without a nitrogen atom or an oxygen atom. 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 group-substituted lower group which may have a lower alkoxy group as a substituent, a halogen atom, a lower alkanoyl group or a phenyl lower alkenylcarbonyl group as a substituent on the phenyl ring. Alkoxy group, tetrazolyl group which may have a lower alkyl group as a substituent on the tetrazole ring, hydroxyl group, 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. R ⁴⁰ and R ⁴¹ are bonded to each other. 5 to 6-membered saturated heterocycles may be bonded to each other with or without other nitrogen atom or oxygen atom to form a 5-membered or 6-membered saturated heterocycle), a lower alkenyloxy group, a nitro group and a substituent. 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) alkenyl group; q) cycloalkyl lower alkyl group; r) naphthyl lower alkyl group; s) phenyl A phenylthio-substituted lower alkyl group which may have a lower alkoxy group as a substituent on the ring; t) have 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]

[Chemical 28]

(In the formula, q represents an integer of 1 to 3.

[0011]

[Chemical 29]

Is a 5- to 14-membered monocyclic, dicyclic or ternary saturated or unsaturated heterocycle having 1 to 4 heteroatoms selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom. A substituted lower alkyl group is shown. R ⁸ is substituted on the above heterocycle, 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. Carbonyl group, phenyl lower alkoxy group which may have amino group which may have lower alkanoyl group as substituent on phenyl ring, carboxy substituted lower alkoxy group, carboxy group, lower alkoxycarbonyl substituted lower alkoxy group, hydroxyl group, lower group 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 the phenyl ring, lower alkoxy-substituted lower alkoxy group, hydroxyl group, Halogen atom and lower alcohol A phenyl group which may have a group selected from the group consisting of a coxy group,
Lower alkenyl group, morpholinocarbonyl lower alkoxy group, lower alkylsulfinyl group, amino group-substituted lower alkyl group, lower alkylthio group, lower group which may have a group selected from the group consisting of lower alkylsulfonyl group and lower alkanoyl group as a substituent 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, amino 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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(In the formula, s represents an integer of 1 to 3.

[0015]

[Chemical 31]

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

[0017]

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(In the formula, t represents an integer of 1 to 3.

[0019]

[Chemical 33]

Is a saturated or unsaturated heterocyclic-substituted lower alkyl group of 5 to 6 membered ring having 1 to 4 heteroatoms selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom. R
⁴⁶ is a substituent on the above heterocycle, and R ⁴⁶ is a hydrogen atom, a lower alkyl group or an oxo group. ), Or a group-(C = O)
lNR ⁹ R ¹⁰ (where l represents 0 or 1. R ⁹ and R
¹⁰ is the same or different and has 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, or a lower alkyl group as a substituent. A certain aminocarbonyl group, a phenylsulfonyl group that 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 which may have,
An amino group-substituted lower alkanoyl group which may have a lower alkanoyl group as a substituent, an 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 is shown. R ⁹ and R ¹⁰ may be bonded to each other with a nitrogen atom to which they are bonded via another nitrogen atom or an oxygen atom or not to form a 5- or 6-membered saturated heterocycle. ). ); X) group -A ₅ -CR ⁴² R ⁴³
R ⁴⁴ (in the formula, A ₅ represents a lower alkylene group. R ⁴² and R
⁴³ shall 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 group-substituted lower alkyl group which may have a group selected from the group consisting of an oxo group as a substituent group, a hydroxyl group and a silyloxy group having a lower alkyl group as a substituent group on the indenyl ring; Or z)
Basis

[0021]

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(In the formula, u represents an integer of 1 to 3.

[0023]

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Is a saturated or unsaturated heterocyclic ring substitution of a 5- to 14-membered monocyclic, binary or ternary ring having 1 to 4 heteroatoms selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom. A lower alkenyl group is shown. R ⁴⁷ is substituted on the above heterocycle, 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 group as a 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, and a group selected from the group consisting of a lower alkoxy group and a halogen atom as a substituent on the phenyl ring. Phenyl group or group

[0025]

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(In the formula, A ₆ , R ⁴⁵ and s are the same as above.)
Indicates. ). A) R ³ and R ⁴ may combine with the nitrogen atom to which they are bonded to form a 1,2,3,4-tetrahydroisoquinolyl group. The heterocycle may have a lower alkoxy group as a substituent. ] It contains at least 1 sort (s) of the compound selected from the group which consists of a quinoxaline derivative and its salt represented by these as an active ingredient.

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

According to WHO type classification, diabetes is caused by acute or subacute symptoms due to lack of absolute amount of insulin, and insulin-dependent diabetes mellitus requiring insulin treatment.
etes mellitus (IDDM), a non-insulin-dependent diabetes mellitus that has a slow progression of diabetes and does not necessarily require insulin treatment.
pendant diabetes mellitu
s, NIDDM), malnutrition-related diabetes (malnu)
trition-related diabetes
(Mellitus, MRDM) and other diseases and chronic hyperglycemia associated with pathological conditions.

Of these, the cause of IDDM is said to be the destruction of pancreatic β cells by an autoimmune mechanism.
The involvement of HLA antigens, cytokine viruses, etc. is considered to be the cause of the pancreatic β-cell destruction (Koji Nakanishi, Tetsuro Kobayashi, Mitsuru Hara: “Diabetes 1989”, edited by Kitonori Kosaka, Yasuo Akanuma, Diagnosis and Treatment Company. , 1989, 226-244
page). On the other hand, the causes of NIDDM include (i) congenital abnormalities in the pancreas, that is, abnormal adaptability to increase insulin demand, and (ii) impaired insulin action caused by various factors such as aging, obesity, and stress. (Yuo Imura: “Advances in Diabetes 1989”,
23rd Edition, Japan Diabetes Society, Diagnosis and Treatment, 1989
1-12).

However, the onset of diabetes is caused by IDDM and NI.
Including DDM, genetic factors and environmental factors are intricately intertwined with each other, and much of the unknown remains.

When looking at tissues in NIDDM, there are two important causes of hyperglycemia: a decrease in glucose uptake in peripheral tissues, particularly muscle tissues, and an increase in glucose release in the liver. It is considered. Currently, the most commonly used drug therapy is insulin or sulfonylurea agents (insulin secretagogues), both of which are based on supplementing deficient insulin, but strict blood glucose control is difficult. However, it may cause high insulin plasma and hypoglycemia. Therefore, a compound that promotes glucose uptake in muscle tissue without promoting insulin secretion becomes a new type of hypoglycemic agent that does not have the risk of high insulin plasma or hypoglycemia, and is useful as a therapeutic drug for diabetes. Conceivable.

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

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

More specifically, each group represented by the above general formula (1) is as follows.

As the lower alkyl group, 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.

As the halogen atom, for example, a fluorine atom,
Examples thereof include chlorine atom, bromine atom and iodine atom.

Examples of the lower alkyl group which may have a halogen atom as a substituent include, 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-
1 to 6 carbon atoms which may have 1 to 3 halogen atoms as a substituent such as 2-methylpropyl, 5-bromohexyl, 5,6-dichlorohexyl, 5-bromohexyl, 5,6-dichlorohexyl group and the like. The straight chain or branched chain alkyl group can be exemplified.

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 morpholinopropyl group has 1 to 6 carbon atoms.
And a morpholino-substituted alkyl group which is a linear or branched alkyl group of

Examples of the imidazolyl-substituted lower alkyl group include (1-imidazolyl) methyl, 2- (1-imidazolyl) ethyl, 1- (2-imidazolyl) ethyl, 3- (4-imidazolyl) propyl, 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 an alkyl moiety such as a 3- (1-imidazolyl) propyl group is a linear or branched alkyl group having 1 to 6 carbon atoms.

Examples of the lower alkylene group include methylene, ethylene, trimethylene, 2-methyltrimethylene, 2,2-dimethyltrimethylene, 1-methyltrimethylene, methylmethylene, ethylmethylene, tetramethylene, pentamethylene and hexamethylene. Number of carbon atoms such as 1
Examples of the straight chain or branched chain alkylene group of 6

Examples of the lower alkoxy group include linear or branched chain 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 and 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, N-methyl-N-hexylamino group and the like include an amino group which may have 1 or 2 linear or branched alkyl groups having 1 to 6 carbon atoms.

Examples of the lower alkyl group which may have a hydroxyl group as a substituent include, 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-
Methyl-3-hydroxypropyl, 2,3-dihydroxyethyl, 3,4-dihydroxybutyl, 5,6-dihydroxyhexyl group and the like, which may have 1 to 3 hydroxyl groups as a substituent, have 1 to 6 carbon atoms directly. 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 straight-chain or branched alkenyloxy group having 2 to 6 carbon atoms such as a 2-hexenyloxy group can be mentioned.

Examples of the lower alkoxy group substituted with a carboxy group include carboxymethoxy, 2-carboxyethoxy, 1-carboxyethoxy, 3-carboxypropoxy, 4-carboxybutoxy, 5-carboxypentyloxy, 6-carboxyhexyloxy, 1 The number of carbon atoms in the alkoxy moiety such as 1,1-dimethyl-2-carboxyethoxy and 2-methyl-3-carboxypropoxy group is 1
The carboxyalkoxy group which is a linear or branched alkoxy group of ~ 6 can be mentioned.

Lower alkoxycarbonyl group As the substituted lower alkoxy group, 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 Alkoxycarbonyl moieties such as ethoxy and hexyloxycarbonylmethoxy groups are linear or branched alkoxycarbonylalkoxy groups having 1 to 6 carbon atoms and are linear or branched alkoxycarbonylalkoxy groups having 1 to 6 carbon atoms. be able to.

The lower alkoxycarbonyl group is, for example, a straight chain having 1 to 6 carbon atoms such as methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, tert-butoxycarbonyl, pentyloxycarbonyl and hexyloxycarbonyl groups. 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
As a substituent such as a -dichlorohexyloxy group, a linear or branched alkoxy group having 1 to 3 halogen atoms and 1 to 6 carbon atoms can be exemplified.

Examples of the hydroxy-substituted lower alkoxy group include hydroxymethoxy, 2-hydroxyethoxy, 1-hydroxyethoxy, 1-hydroxypropoxy, 3-hydroxypropoxy, 2,3-dihydroxypropoxy, 4-hydroxybutoxy, 1, 1-dimethyl-2-hydroxyethoxy, 5,5,4-trihydroxypentyloxy, 5-hydroxypentyloxy, 6-hydroxyhexyloxy, 1-hydroxyisopropoxy, 2-methyl-3-hydroxypropoxy, 2,3 -Dihydroxyethoxy, 3,4-dihydroxybutoxy, 5,6-dihydroxyhexyloxy group and the like having 1 to 3 carbon atoms having 1 to 3 hydroxyl groups as a substituent.
The straight chain or branched chain alkoxy group can be exemplified.

Examples of the phenyl lower alkoxy group which may have a group selected from the group consisting of a lower alkyl group and a lower alkoxy group on the phenyl ring include 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, 2 , 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) propokin, 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
-The number of carbon atoms of the alkoxy moiety such as dimethylbenzyloxy and 2-methoxy-3-methylbenzyloxy group is 1 to 6
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. There may be mentioned 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 is added in an amount of 1 to 3
The 1,3-dioxolanyl group which may have one can be exemplified.

Examples of the lower alkanoyl group include straight-chain or branched-chain 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,
The alkoxy moiety such as 1,1-dimethyl-2- (2-morpholinyl) ethoxy, 5-morpholinopentyloxy, 6-morpholinohexyloxy, 2-methyl-3-morpholinopropoxy group is a straight chain having 1 to 6 carbon atoms or A morpholino-substituted alkoxy group which is a branched chain alkoxy group can be exemplified.

As the phenyl lower alkyl group, for example, benzyl, 2-phenylethyl, 1-phenylethyl,
The alkyl moiety such as 3-phenylpropyl, 4-phenylbutyl, 5-phenylpentyl, 6-phenylhexyl, 1,1-dimethyl-2-phenylethyl, 2-methyl-3-phenylpropyl group has 1 to 6 carbon atoms. And a phenylalkyl group which is a straight chain or branched chain alkyl group.

The phenyl lower alkyl group which may have a lower alkoxy group as a substituent on the phenyl ring includes 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,
Alkyl moiety such as 3,4-dimethoxybenzyl, 2,4-dimethoxybenzyl, 3,4,5-trimethoxybenzyl group is a linear or branched alkyl group having 1 to 6 carbon atoms, 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
The alkyl moiety such as -furyl) propyl group has 1 to 6 carbon atoms.
And a furyl-substituted alkyl group which is a straight chain or branched chain alkyl group.

As the lower alkoxy lower alkyl group,
For example, methoxymethyl, 2-ethoxyethyl, 1-methoxyethyl, 3-methoxypropyl, 4-ethoxybutyl, 6-propoxyhexyl, 5-isopropoxypentyl, 1,1-dimethyl-2-butoxyethyl, 2-methyl- A straight chain or branched chain having 1 to 6 carbon atoms in which an 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.

A lower alkoxy group substituted with a lower alkoxy group, a halogen atom, a lower alkanoyl group as a substituent, and a group selected from the group consisting of a phenyl lower alkenylcarbonyl group on the phenyl ring, which may have an amino group or a lower alkoxy group. 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 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 and 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, 4
-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, 2 -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-butyl 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
-Hydroxy-5-chlorophenyl) -2-butenyl group and the like is an alkenyl group having 1 to 2 straight or branched double bonds having 2 to 6 carbon atoms in the alkenyl moiety, and on the phenyl ring Is a straight-chain or branched-chain alkoxy group having 1 to 6 carbon atoms, a halogen atom, a straight-chain or branched-chain alkanoyl group having 1 to 6 carbon atoms as a substituent, and an alkenylcarbonyl moiety having 3 to 6 carbon atoms. An amino group which may have 1 or 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 represents a linear or branched alkylene group having 1 to 6 carbon atoms. R ⁴⁰ and R ⁴¹ are the same or different and each is a hydrogen atom or a straight chain 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 a nitrogen atom to which they are bonded via another nitrogen atom or an oxygen atom or not to form a 5- or 6-membered saturated heterocycle. ), A linear or branched alkenyloxy group having 2 to 6 carbon atoms, a nitro group, and a linear or branched alkyl group having 1 to 6 carbon atoms which may have 1 to 3 halogen atoms as a substituent. Mention may be made of phenylalkenyl groups which may have 1 to 3 groups selected from the group consisting of.

Examples of the alkenyl group include vinyl, allyl, 3-methyl-2-butenyl, 2-butenyl and 3-
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-. Four
-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-decadienyl, 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-dodecadienyl, 3-methyl-2,5-dodecadienyl, 4,8-dimethyl-2,6-dodecadienyl, 2,4,6-trimethyl-2,7-dodecadienyl, 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-
1 to 3 linear or branched double bonds having 2 to 12 carbon atoms such as dodecatrienyl and 1,5,7-undecatrienyl group
The alkenyl group which has three can be illustrated.

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 Examples of such alkyl moieties include cycloalkylalkyl groups having 3 to 8 carbon atoms, which are linear or branched alkyl groups having 1 to 6 carbon atoms.

As the naphthyl lower alkyl group, for example, α-naphthylmethyl, β-naphthylmethyl, 2-
(Α-naphthyl) ethyl, 1- (β-naphthyl) ethyl, 3- (β-naphthyl) propyl, 4- (α-naphthyl) butyl, 2-methyl-3- (α-naphthyl) propyl, 5- ( β-naphthyl) pentyl, 6- (α-naphthyl) hexyl, 1,1-dimethyl-2- (β-naphthyl) ethyl and other alkyl moieties are straight or branched chain alkyl groups having 1 to 6 carbon atoms. An example is a naphthylalkyl group.

Examples of the phenylthio-substituted lower alkyl group which may have a lower alkoxy group as a substituent on the phenyl ring include, 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 or other alkyl moiety which may have 1 to 3 linear or branched alkoxy groups having 1 to 6 carbon atoms as a substituent on the phenyl ring. Examples thereof include a phenylthioalkyl group which is a linear or branched alkyl group having 1 to 6 carbon atoms.

Examples of the phenylsulfinyl-substituted lower alkyl group which may have a lower alkoxy group as a substituent on the phenyl ring include, for example, phenylsulfinylmethyl, 2-phenylsulfinylethyl, 1-phenylsulfinylethyl and 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 group and the like having 1 to 6 carbon atoms as a substituent on the phenyl ring. The 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, can be exemplified.

Examples of the phenylsulfonyl-substituted lower alkyl group which may have a lower alkoxy group as a substituent on the phenyl ring include, 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, 1 or more linear or branched alkoxy group having 1 to 6 carbon atoms as a substituent on the phenyl ring such as 6-dimethoxyphenylsulfonyl) ethyl or 2- (3,4,5-trimethoxyphenylsulfonyl) ethyl group. 1 to 3 carbon atoms in the alkyl moiety that may have
The phenylsulfonylalkyl group which is a linear or branched alkyl group of ~ 6 can be exemplified.

As a 5- to 14-membered monocyclic, dicyclic or ternary saturated or unsaturated heterocyclic group having 1 to 4 heteroatoms selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom. Is, for example, pyrrolidinyl, piperidinyl, piperazinyl, morpholino, pyridyl, thienyl, quinolyl, 1,
4-dihydroquinolyl, benzothiazolyl, pyrazinyl, pyrimidyl, pyridazinyl, pyrrolyl, carbostyril, 3,4-dihydrocarbostyril, 1,2,3,3
4-tetrahydroquinolyl, indolyl, isoindolyl, indolinyl, benzimidazolyl, benzoxazolyl, imidazolidinyl, isoquinolyl, quinazolidinyl, quinoxalinyl, cinnonyl, phthalazinyl, chromanyl, isoindolinyl, isochromanil, pyrazolyl, imidazolyl, pyrazolidinyl, 2,3-didiyl. , Perihydrobenzofuryl, benzofuryl, benzothienyl, 4H-chromenil, 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 Furo [2.3-g] quinolyl, 1,4-benzodioxanyl, 1,2,4-triazinyl, naphtho [2,1
Examples thereof include -b] furyl and imidazo [1,2-a] pyridyl groups.

5- to 14-membered monocyclic, dicyclic or ternary saturated or unsaturated heterocyclic-substituted lower having 1 to 4 heteroatoms selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom Examples of the alkyl group include pyrrolidinylmethyl and 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, 5
-(3-Carbostyryl) pentyl, 6- (3,4-dihydrocarbostyryl-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-pyrrolinyl) 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- (1,2,3,3) 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 linear or branched 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.

As the phenoxy-substituted lower alkyl group,
For example, phenoxymethyl, 2-phenoxyethyl, 1
-Phenoxyethyl, 3-phenoxypropyl, 4-phenoxybutyl, 5-phenoxypentyl, 6-phenoxyhexyl, 1,1-dimethyl-2-phenoxyethyl, 2-methyl-3-phenoxypropyl and the like are carbon atoms. Examples thereof include a phenoxyalkyl group which is a linear or branched alkyl group having a number of 1 to 6.

Examples of 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 include, for example, benzyloxy, 2-phenylethoxy, 1-phenylethoxy,
3-phenylpropoxy, 4-phenylbutoxy, 5-
Phenylpentyloxy, 6-phenylhexoxy,
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 group is a straight-chain or branched-chain alkoxy group having 1 to 6 carbon atoms, and has 1 to 6 carbon atoms as a substituent on the phenyl ring. Mention may be made of phenylalkoxy groups which may have 1 to 3 amino groups which may have branched alkanoyl groups.

Lower alkoxy substituted lower alkoxy groups include, for example, methoxymethoxy, 3-methoxypropoxy, 4-ethoxybutoxy, 6-propoxyhexyloxy, 5-isopropoxypentyloxy, 1,1-dimethyl-2-butoxyethoxy, 2-methyl-3-te
C1-C6 linear or branched alkoxy groups such as rt-butoxypropoxy, 2-pentyloxyethoxy, hexyloxymethoxy groups, etc. are mentioned, and C1-C6 linear or branched alkoxy groups are mentioned. be able to.

Examples of the lower alkanoyloxy group-substituted lower alkyl group include acetyloxymethyl and 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 hexanoyloxyethyl or 2-methyl-3-acetyloxypropyl group, is substituted with a linear or branched alkyl group having 1 to 6 carbon atoms. Can be mentioned.

As the halogen atom-substituted lower alkyl group, for example, 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-
2-methylpropyl, 5-bromohexyl, 5,6-dichlorohexyl, 5-bromohexyl, 5,6-dichlorohexyl group and the like having 1 to 3 halogen atoms as a substituent and a straight chain having 1 to 6 carbon atoms Alternatively, a branched chain 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 and 5-propyl. A linear or branched alkyl group having 1 to 6 carbon atoms as a substituent on the tetrazole ring such as tetrazolyl, 1-butyltetrazolyl, 2-pentyltetrazolyl, 1-hexyltetrazolyl group. The tetrazolyl group which may have can be illustrated.

The phenyl group which may have a group 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 is, for example, phenyl, 2 -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-
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
1 to 6 carbon atoms as a substituent on the phenyl ring such as-(2-pentyloxyethoxy) phenyl, 4-hexyloxymethoxyphenyl, 2,3-dimethoxymethoxyphenyl, 3,4,5-trimethoxymethoxyphenyl group. Linear or branched alkyl group, linear or branched alkoxy group having 1 to 6 carbon atoms, substituted or unsubstituted linear or branched alkoxy group having 1 to 6 carbon atoms, hydroxyl group, halogen atom and carbon number 1
Examples of the phenyl group may have 1 to 3 groups selected from the group consisting of linear to branched alkoxy groups of 1 to 6.

The lower alkenyl group is, for example, a 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. A group can be mentioned.

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-
Examples thereof include a morpholinocarbonylalkoxy group in which an alkoxy moiety such as a methyl-3-morpholinocarbonylpropoxy group is a linear or branched alkoxy group having 1 to 6 carbon atoms.

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

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

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-
The alkenylcarbonyl group such as hexenoyl, 2-methyl-4-phenyl-3-butenoyl, 2-methyl-cinnamoyl, 1-methyl-cinnamoyl group is a linear or branched alkenylcarbonyl group having 3 to 6 carbon atoms. An example is a phenylalkenylcarbonyl group.

R ⁶ and R ⁷ , R ⁹ and R ¹⁰ , R ⁴⁰ and R
⁴¹ or a 5- or 6-membered saturated heterocyclic group formed together with the nitrogen atom to which R ⁵² and R ⁵³ are bound through a nitrogen atom or an oxygen atom or not, for example, pyrrolidinyl, piperidinyl, piperazinyl, A morpholino group etc. can be illustrated.

Examples of the above-mentioned 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 include, for example, 3-hydroxypyrrolidinyl, 2-hydroxypyrrolidinyl, 4 -Hydroxypiperidinyl, 3-hydroxypiperidinyl, 2-hydroxypiperidinyl, 3-hydroxypiperazinyl, 2-hydroxypiperazinyl, 3-hydroxymorpholino, 2
-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-trimethylpyrrolidinyl Peridinyl, 4-butylpiperidinyl, 3-pentylmorpholino, 2-hexylpiperazinyl, 3-methyl-4-benzylpiperazinyl, 3-ethyl-4-hydroxypiperidinyl, 3-
A hydroxyl group such as 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; 1-3 groups selected from the group consisting of certain phenylalkyl groups
The above-mentioned heterocyclic groups having one 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 as a substituent include, for example, amino, formylamino, acetylamino, propionylamino, butyrylamino, isobutyl. 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 straight-chain or branched-chain alkanoyl group having 1 to 6 carbon atoms and a phenylalkenyl in which the alkenylcarbonyl moiety is a straight-chain or branched alkenylcarbonyl group having 3 to 6 carbon atoms as a substituent such as a cinnamoylamino group. An amino group which may have 1 or 2 groups selected from the group consisting of a carbonyl 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 and hexa. An amino group which may have a linear or branched alkanoyl group having 1 to 6 carbon atoms as a substituent such as a noylamino group can be exemplified.

Examples of the lower alkylsulfinyl group include methylsulfinyl, ethylsulfinyl, isopropylsulfinyl, butylsulfinyl and tert-.
Examples thereof include linear or branched alkylsulfinyl groups having 1 to 6 carbon atoms such as butylsulfinyl, pentylsulfinyl and hexylsulfinyl groups.

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

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

The lower alkanoyloxy group is, for example, formyloxy, acetyloxy, propionyloxy, butyryloxy, isobutyryloxy, pentanoyloxy, tert-butylcarbonyloxy, hexanoyloxy group and the like having 1 to 6 carbon atoms. A straight chain or branched chain alkanoyloxy group can be exemplified.

Examples of the 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 include, 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,
1,1-dimethyl-2-methylsulfonylaminoethyl, 2-methyl-3-ethylsulfonylaminopropyl, N-methylsulfonylamino-N-acetylaminomethyl group and the like straight-chain or having 1 to 6 carbon atoms as a substituent. 1 to 2 groups 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 linear or branched alkyl groups having 1 to 6 carbon atoms and having an amino group which may be present.

Examples of the 1,3-dioxofuranyl-substituted lower alkyl group which may have a lower alkyl group as a substituent include (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-dioxolane-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 linear or branched alkyl group having 1 to 6 carbon atoms, and a linear or branched alkyl group 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.

Examples of the lower alkyl group substituted with a lower alkanoyl group include formylmethyl, acetylmethyl and 2
-Propionylethyl, 1-butyrylethyl, 3-isobutyrylpropyl, 4-pentanoylbutyl, 5-hexanoylhexyl, 6-tert-butylcarbonylhexyl, 1,1-dimethyl-2-acetylethyl, 2-
The alkanoyl moiety such as a methyl-3-acetylmethyl group is a straight chain or branched chain alkanoyl group having 1 to 6 carbon atoms, and the alkyl moiety is a straight chain or branched chain alkyl group having 1 to 6 carbon atoms. An example is an alkanoylalkyl group.

As the aminocarbonyl-substituted lower alkyl group which may have a lower alkyl group as a substituent,
For example, aminocarbonylmethyl, 2-aminocarbonylethyl, 1-aminocarbonylethyl, 3-aminocarbonylpropyl, 4-aminocarbonylbutyl, 5-
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 and the like having 1 or 2 straight or branched chain alkyl group having 1 to 6 carbon atoms as a substituent. A linear or branched alkyl group having 1 to 6 carbon atoms having a certain aminocarbonyl group can be exemplified.

Examples of the lower alkoxycarbonyl group-substituted lower alkenyl group include 2-methoxycarbonylvinyl, 2-ethoxycarbonylvinyl, 3-propoxycarbonylallyl, 4-butoxycarbonyl-2-butenyl and 4-pentyloxycarbonyl-3. -Butenyl,
3-hexyloxycarbonyl-1-methylallyl, 5
-Isopropoxycarbonyl-2-pentenyl, 6-t
ert-butoxycarbonyl-2-hexenyl group and other alkenyl moieties are straight-chain or branched-chain alkenyl groups having 2-6 carbon atoms, and straight-chain or branched-chain alkoxycarbonyl group-substituted alkenyl groups having 1-6 carbon atoms. Can be illustrated.

Examples of the aminocarbonyl group-substituted lower alkenyl group which may have a lower alkyl group as a substituent include 2-aminocarbonylvinyl, 3-aminocarbonylallyl, 4-aminocarbonyl-2-butenyl and 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 has 2 to 8 carbon atoms which is substituted with an aminocarbonyl group which may have 1 to 2 linear or branched alkyl group having 1 to 6 carbon atoms as a substituent. 6 straight-chain or branched alkenyl groups can be exemplified.

Examples of the lower alkenyl group substituted with a carboxy 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
-C2-having a carboxy group such as a hexenyl group substituted
6 straight-chain or branched alkenyl groups can be exemplified.

Examples of the aminocarbonyl group which may have a lower alkyl group as a substituent include, for example, aminocarbonyl, methylaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl, isopropylaminocarbonyl, butylaminocarbonyl and tert-butylaminocarbonyl. , Pentylaminocarbonyl, hexylaminocarbonyl, dimethylaminocarbonyl,
Diethylaminocarbonyl, dipropylaminocarbonyl, dibutylaminocarbonyl, dipentylaminocarbonyl, dihexylaminocarbonyl, N-methyl-N
-Ethylaminocarbonyl, N-ethyl-N-propylaminocarbonyl, N-methyl-N-butylaminocarbonyl, N-methyl-N-hexylaminocarbonyl group or the like as a substituent, a straight or branched chain having 1 to 6 carbon atoms. An aminocarbonyl group which may have 1 or 2 branched chain 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,
Examples thereof include a phenylsulfonyl group which may have 1 to 3 linear or branched alkyl groups having 1 to 6 carbon atoms as a substituent on the phenyl ring such as a 3,4,5-trimethylphenylsulfonyl group.

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
-Hexenyl, 6-phenyl-2-hexenyl, 2-methyl-4-phenyl-3-butenyl, 2-methyl-cinnamyl, 1-methyl-cinnamyl group and the like, the alkenyl moiety is a straight or branched chain having 2 to 6 carbon atoms. Examples thereof include a phenylalkenyl group which is a branched alkenyl group.

As a benzoyl group which may have 1 to 3 groups selected from the group consisting of 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 on the phenyl ring. 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, 2
-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, 2 -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, or a substituent on the phenyl ring such as a 2,4,6-trihydroxybenzoyl or 2-hydroxy-5-chlorobenzoyl group as a substituent. Examples thereof include 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.

As the amino group-substituted lower alkanoyl group which may have a lower alkanoyl group as a substituent,
For example, 2-aminoacetyl, 3-aminopropionyl, 2-aminopropionyl, 4-aminobutyryl, 5
-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 2 carbon atoms having an amino group which may have 1 or 2 linear or branched alkanoyl groups having 1 to 6 carbon atoms as a substituent such as aminohexanoyl and 2-formylaminoacetyl group
Examples of the straight-chain or branched-chain alkanoyl group represented by:

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 -N-propylaminosulfonyl, N-methyl-N-butylaminosulfonyl, N-methyl-N-hexylaminosulfonyl group or the like may be substituted with 1 to 6 linear or branched alkyl groups having 1 to 6 carbon atoms. The aminosulfonyl group which may have two can be illustrated.

The lower alkylenedioxy group includes, for example, methylenedioxy, ethylenedioxy, trimethylenedioxy, tetramethylenedioxy groups and the like having 1 to 1 carbon atoms.
The linear or branched alkylenedioxy group of 4 can be exemplified.

Examples of the phenyl group which may have a lower alkoxy group as a substituent on the phenyl ring include, 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 such as a 4,5-trimethoxyphenyl group which may have 1 to 3 linear or branched alkoxy groups having 1 to 6 carbon atoms on the phenyl ring as a substituent can be exemplified.

2,3-dihydro-1H-indenyl ring may have 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. Examples of the lower alkyl group substituted with a dihydro-1H-indenyl group include (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 the 2,3-dihydro-1H-indenyl ring such as 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 straight chain or branched chain having 1 to 6 carbon atoms substituted with 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 trimethylsilyloxy, triethylsilyloxy, triisopropylsilyloxy, tributylsilyloxy, tri-tert-butylsilyloxy, tripentylsilyloxy, trihexylsilyl. Examples thereof include silyloxy groups in which three linear 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 lower alkoxy group as a substituent and a group selected from the group consisting of a halogen atom on the phenyl ring include, for example, phenyl and 2-
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-
1 to 5 carbon atoms as a substituent on the phenyl ring such as 5-bromophenyl and 3,5-diiodo-4-methoxyphenyl group
Examples thereof include a phenyl group which may have 1 to 3 groups selected from the group consisting of linear or branched alkoxy groups of 6 and halogen atoms.

Examples of the 5- or 6-membered saturated or unsaturated heterocyclic group having 1 to 4 heteroatoms selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom include, for example, pyrrolidinyl, piperidinyl, piperazinyl and morpholino. , Pyridyl, thienyl, pyrazinyl, pyrimidyl, pyridazinyl, pyrrolyl, imidazolinyl, 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 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 to 4 heteroatoms selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom include 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-pyrrolinyl) 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,
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- (thiazolidin-2-yl) propyl, 4- (1,2,3,5-oxathiadiazoline-4
Examples of the heterocyclic-substituted alkyl group whose alkyl moiety such as -yl) butyl group is a linear or branched alkyl group having 1 to 6 carbon atoms.

A 5- to 14-membered monocyclic, dicyclic or ternary saturated or unsaturated heterocyclic-substituted lower having 1 to 4 heteroatoms selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom. 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-benzothienyl vinyl, 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-
(Furo [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-
Dihydrocarbostyryl) -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-pyrrolidinyl vinyl, 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-piperidinyl vinyl, 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-pentadienyl, 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-piperazinyl vinyl, 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-pyridazinyl vinyl, 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-imidazolidinyl vinyl, 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-pentadienyl , 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-pyrazolyl vinyl, 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 [2,2 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 [2,2
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)
The alkenyl moiety such as 2-propenyl and 4- (imidazo [1,2-a] pyridyl) -3-butenyl group has 2 carbon atoms.
The heterocyclic-substituted alkenyl groups which are alkenyl groups having 1 to 2 linear or branched double bonds of 6 to 6 can be mentioned.

As the phenyl lower alkoxycarbonyl group, for example, benzyloxycarbonyl, 2-phenylethoxycarbonyl, 1-phenylethoxycarbonyl, 3-phenylpropoxycarbonyl, 4-phenylbutoxycarbonyl, 5-phenylpentyloxycarbonyl, 6- 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.

Examples of the lower alkoxycarbonyloxy-substituted lower alkyl group include methoxycarbonyloxymethyl, ethoxycarbonyloxymethyl, 2-ethoxycarbonyloxyethyl, 1-ethoxycarbonyloxyethyl, 3-methoxycarbonyloxypropyl and 4-ethoxy. Carbonyloxybutyl, 6-propoxycarbonyloxyhexyl, 5-isopropoxycarbonyloxypentyl, 1,1-dimethyl-2-butoxycarbonyloxyethyl, 2-methyl-3-ter
Alkyl moieties such as t-butoxycarbonyloxypropyl, 2-pentyloxycarbonyloxyethyl and hexyloxycarbonyloxymethyl groups are straight-chain or branched-chain alkyl groups having 1 to 6 carbon atoms and directly 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 and 3 -(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 group and the like may have 1 to 3 halogen atoms as a substituent on the phenyl ring, and the alkyl moiety may be 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 and hexa. An amino group which may have a linear or branched alkanoyl group having 1 to 6 carbon atoms as a substituent such as a noylamino group can be exemplified.

The compounds of the present invention include the following compounds.

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

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

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

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

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

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

(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, or 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, or 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 [Chemical formula 27], and R ¹ , R ² , m, n and r
Is a quinoxaline derivative represented by the general formula (1) or a salt thereof, which is the same as above.

(10) R ³ is a lower alkyl group, R ⁴ is a group represented by the above [Chemical formula 27], and R ¹ , R ² , m, n and r are the same as those defined above. A quinoxaline derivative represented by or a salt thereof.

(11) R ³ represents a hydrogen atom, and R ⁴ is a group selected from the group consisting of a lower alkoxy group as a substituent, a halogen atom, a lower alkanoyl group as a substituent and a phenyl lower alkenylcarbonyl group on the phenyl ring. Optionally having an amino group, a lower alkoxy group-substituted lower alkoxy group, a tetrazolyl group having a lower alkyl group as a substituent on the tetrazole ring, a hydroxyl group, and 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 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 are the same as those described above.

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

(13) A quinoxaline derivative represented by the general formula (1) in which 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 above. Or its salt.

(14) R ³ represents 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 general formula (1) or a salt thereof, which is the same as above.

(15) R³Represents a hydrogen atom, R^FourSiku
Represents a lower alkyl group, R ¹, R², M, n
And r are the same as above, and the quinone represented by the general formula (1)
Xaline derivatives or salts thereof.

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

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

(18) R ³ represents a lower alkyl group, R ⁴
Represents a naphthyl lower alkyl group, 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.

(19) R ³ represents a hydrogen atom, 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 defined above, or a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(20) R ³ represents 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,
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.

(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 the phenyl ring, 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.

(22) R ³ represents 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 general formula (1). A quinoxaline derivative or a salt thereof.

(23) R ³ represents a hydrogen atom, R ⁴ represents a phenylsulfonyl-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 defined above, or a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(24) R ³ represents 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 the same as those described above and are represented by the general formula (1). A quinoxaline derivative or a salt 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, a quinoxaline derivative represented by the general formula (1) or a salt thereof.

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

(27) R ³ represents a hydrogen atom, R ⁴ represents a group represented by the above [formula 28], and R ¹ , R ² , m, n and r are the same as those in the general formula (1). ) The quinoxaline derivative or its salt shown by these.

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

(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 defined above) shows ^{a, R 1, R 2, m} , the general formula n and r are the same as defined above (1 ) The quinoxaline derivative or its salt shown by these.

(30) R ³ represents a lower alkyl group, R ⁴
There group _{^{-A 5 -CR 42 R 43 R 44}} (A 5, R 42, R 43 and R
⁴⁴ is the same as the above), and R ¹ , R ² , m, n and r are the same as the above, or 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,
A 2,3-dihydro-1H-indenyl group which 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 3-dihydro-1H-indenyl ring. A quinoxaline derivative represented by the general formula (1) or a salt thereof, which represents a substituted lower alkyl group, and R ¹ , R ² , m, n and r are the same as defined above.

(32) R ³ represents a lower alkyl group, R ⁴
May have 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 on the 2,3-dihydro-1H-indenyl ring. A quinoxaline derivative represented by the general formula (1) or a salt thereof, which represents a lower alkyl group substituted with an indenyl group, and R ¹ , R ² , m, n and r are the same as defined above.

(33) R ³ represents a hydrogen atom, R ⁴ represents a group represented by the above [Chemical Formula 34], and R ¹ , R ² , m, n and r are the same as those in the general formula (1). ) The quinoxaline derivative or its salt shown by these.

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

(35) 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 (having a lower alkoxy group on the 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 a salt thereof.

(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.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein (9) or (10) is defined and m, n and r are the same as defined above.

(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.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, which has the definition of (11) or (12) and m, n and r are the same as defined above.

(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.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, which has the definition of (13) or (14) and m, n and r are the same as defined above.

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

(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.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein (17) or (18) is defined and m, n and r are the same as defined above.

(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.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein (17) or (18) is defined and m, n and r are the same as defined above.

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

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

(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.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, which has the definition of (23) or (24) and m, n and r are the same as defined above.

(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.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein the definition of (25) or (26) is shown and m, n and r are the same as defined above.

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

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

(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.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein (31) or (32) is defined and m, n and r are the same as defined above.

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

(50) R ¹ represents the definition of (2) or (3), R ² represents the definition of (4), and R ³ and R ⁴ represent the above.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein definition of (35) is shown and m, n and r are the same as above.

(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.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein (9) or (10) is defined and m, n and r are the same as defined above.

(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.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, which has the definition of (11) or (12) and m, n and r are the same as defined above.

(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.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, which has the definition of (13) or (14) and m, n and r are the same as defined above.

(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.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, which has the definition of (15) or (16) and m, n and r are the same as defined above.

(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.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein (17) or (18) is defined and m, n and r are the same as defined above.

(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.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, which has the definition of (19) or (20) and m, n and r are the same as defined above.

(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.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein the definition is (21) or (22), and m, n and r are the same as defined above.

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

(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.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein the definition of (25) or (26) is shown and m, n and r are the same as defined above.

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

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

(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.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein (31) or (32) is defined and m, n and r are the same as defined above.

(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.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein (33) or (34) is defined and m, n and r are the same as defined above.

(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.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein definition of (35) is shown and m, n and r are the same as above.

(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.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein (9) or (10) is defined and m, n and r are the same as defined above.

(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.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, which has the definition of (11) or (12) and m, n and r are the same as defined above.

(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.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, which has the definition of (13) or (14) and m, n and r are the same as defined above.

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

(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.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein (17) or (18) is defined and m, n and r are the same as defined above.

(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.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, which has the definition of (19) or (20) and m, n and r are the same as defined above.

(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.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein the definition is (21) or (22), and m, n and r are the same as defined above.

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

(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.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein the definition of (25) or (26) is shown and m, n and r are the same as defined above.

(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.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein the definition of (27) or (28) is shown and m, n and r are the same as defined above.

(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.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein (29) or (30) is defined and m, n and r are the same as defined above.

(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.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein (31) or (32) is defined and m, n and r are the same as defined above.

(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.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein (33) or (34) is defined and m, n and r are the same as defined above.

(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.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein definition of (35) is shown and m, n and r are the same as above.

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

(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.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, which has the definition of (11) or (12) and m, n and r are the same as defined above.

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

(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.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, which has the definition of (15) or (16) and m, n and r are the same as defined above.

(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.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein (17) or (18) is defined and m, n and r are the same as defined above.

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

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

(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.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, which has the definition of (23) or (24) and m, n and r are the same as defined above.

(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.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein the definition of (25) or (26) is shown and m, n and r are the same as defined above.

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

(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.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein (29) or (30) is defined and m, n and r are the same as defined above.

(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 (31) or (32) is defined and m, n and r are the same as defined above.

(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.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein (33) or (34) is defined and m, n and r are the same as defined above.

(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.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein definition of (35) is shown and m, n and r are the same as above.

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

(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.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, which has the definition of (11) or (12) and m, n and r are the same as defined above.

(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.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, which has the definition of (13) or (14) and m, n and r are the same as defined above.

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

(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.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein (17) or (18) is defined and m, n and r are the same as defined above.

(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.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, which has the definition of (19) or (20) and m, n and r are the same as defined above.

(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.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein the definition is (21) or (22), and m, n and r are the same as defined above.

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

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

(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.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein the definition of (27) or (28) is shown and m, n and r are the same as defined above.

(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.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein (29) or (30) is defined and m, n and r are the same as defined above.

(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 (31) or (32) is defined and m, n and r are the same as defined above.

(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.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein (33) or (34) is defined and m, n and r are the same as defined above.

(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.
A quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein definition of (35) is shown and m, n and r are the same as above.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

(127) R ¹ represents the definition of the above (1), 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 general formula (1) or a salt thereof, which is the same as above.

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

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

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

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

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

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

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

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

(136) R ¹ represents an aminocarbonyl 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, or a quinoxaline derivative represented by the general formula (1) or a salt thereof.

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

(138) R ³ is a lower alkanoyloxy-substituted lower alkyl group, R ⁴ is a group represented by the above [Chemical formula 27], 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, and R ⁴ is selected from the group consisting of a lower alkoxy group as a substituent, a halogen atom, a lower alkanoyl group as a substituent and a phenyl lower alkenylcarbonyl group on the phenyl ring. Amino group which may have a lower group, 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, and a group —O—A ₄ —CO—NR ⁴⁰ R ⁴¹
(A ₄ , R ⁴⁰ and R ⁴¹ are the same as above), a lower alkenyloxy group, a nitro group and a 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. Represents an alkenyl group, 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.

(140) A group in which R ³ represents a lower alkanoyloxy-substituted lower alkyl group, R ⁴ represents a lower alkoxy group as a substituent, a halogen atom, a lower alkanoyl group as a substituent and a phenyl lower alkenylcarbonyl group on the 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 the same 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, wherein R ¹ , R ² , m, n and r are the same as those defined above.

(141) R ³ represents a phenyl lower alkoxycarbonyl group, R ⁴ represents a lower alkenyl group,
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.

(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 those in the general formula (1). A quinoxaline derivative represented by 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 are the same as those in the general formula (1). A quinoxaline derivative represented by 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 ( A quinoxaline derivative represented by 1) or a salt thereof.

(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 general formula (1). The indicated quinoxaline derivative or its salt.

(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). ) The quinoxaline derivative or its salt shown by these.

(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, and R ¹ , R ² and m , N and r are the same as defined above, or 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 the phenyl ring, and R ¹ , R ² , M, n and r
Is a quinoxaline derivative represented by the general formula (1) or a salt thereof, which is the same as above.

(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 , The quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as above.

(150) R ³ represents a lower alkanoyloxy-substituted 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,
The quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein n and r are the same as described above.

(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 general formula (1) or a salt thereof, which is the same as above.

(152) R ³ represents a lower alkanoyloxy-substituted 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 and 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.

(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 defined above in formula (1) A quinoxaline derivative represented by 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 are the same as those in the general formula ( A quinoxaline derivative represented by 1) or a salt thereof.

(155) R ³ represents a phenyl lower alkoxycarbonyl group, R ⁴ represents a group represented by the above [Chemical Formula 28], 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 [Chemical Formula 28], and R ¹ , R ² , m, n and r are the same as defined above. A quinoxaline derivative represented by the 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 and
The quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as above.

(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 the same as defined above), 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.

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

(160) R ³ represents a lower alkanoyloxy-substituted lower alkyl group, and R ⁴ represents 2,3-dihydro-1H
A 2,3-dihydro-1H-indenyl group-substituted lower alkyl group which may have 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 on the indenyl ring. Show, 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.

(161) R ³ represents a phenyl lower alkoxycarbonyl group, R ⁴ represents a group represented by the above [Chemical Formula 34], 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 [Chemical Formula 34], and R ¹ , R ² , m, n and r are the same as defined above. A quinoxaline derivative represented by the general formula (1) or a salt thereof.

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

(164) R ³ represents a lower alkoxycarbonyl group, R ⁴ represents a group represented by the above [Chemical Formula 27], and R ¹ and R
² , quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as 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 Optionally a tetrazolyl group, a hydroxyl group, a group —O—A ₄ —CO—NR ⁴⁰ R ⁴¹ (A ₄ , R ⁴⁰ and R ⁴¹ are the same as above), 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 R ¹ , R ² , m and n
And r are the same as described above, a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(166) R³Is a lower alkoxycarbonyl group
Indicates R^FourIs a lower alcohol as a substituent on the phenyl ring
Xy group, halogen atom, lower alkanoyl as a substituent
Group and phenyl lower alkenylcarbonyl group
Amino group that may have a selected group, lower alkoxy
Si group-substituted lower alkoxy group, substituent on tetrazole ring
May have a lower alkyl group as
Group, hydroxyl group, group -OA _Four-CO-NR⁴⁰R
⁴¹(A_Four, R⁴⁰And R⁴¹Is the same as above), lower alkeni
Roxy group, nitro group and halogen atom as 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, R², M, n and r are the same as above
A 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 defined above.

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

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

(170) R ³ represents a lower alkoxycarbonyl group, R ⁴ represents a cycloalkyl lower alkyl group,
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.

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

(172) R ³ represents a lower alkoxycarbonyl group, R ⁴ represents a naphthyl lower alkyl group, 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.

(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 the same as those described above in the general formula (1). 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 the phenyl ring, R ¹ , R ² , m, The quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein n and r are the same as described above.

(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 described above in the general formula (1). The indicated quinoxaline derivative or its salt.

(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 the phenyl ring, and R ¹ , R ² and m , N and r are the same as defined above, or 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 on the phenyl ring as a substituent, and R ¹ , R ² , m, n and r are the same as those defined above in the general formula (1). The indicated quinoxaline derivative or its salt.

(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 the phenyl ring, and R ¹ , R ² and m , N and r are the same as defined above, or a quinoxaline derivative represented by the general formula (1) or a salt thereof.

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

(180) R ³ represents a lower alkoxycarbonyl group, R ⁴ represents a phenoxy-substituted lower alkyl group,
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.

(181) R ³ represents a lower alkanoyl group,
R ⁴ represents a group represented by the above [Chemical Formula 28], 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.

(182) R ³ represents a lower alkoxycarbonyl group, R ⁴ represents a group represented by the above [Chemical Formula 28], 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.

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

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

(185) R ³ represents a lower alkanoyl group,
2,3-dihydro in which R ⁴ may have 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 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 general formula (1) or a salt thereof, which is the same as above.

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

(187) R ³ represents a lower alkanoyl group,
R ⁴ represents a group represented by the above [Chemical Formula 34], 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.

(188) R ³ represents a lower alkoxycarbonyl group, R ⁴ represents a group represented by the above [Chemical Formula 34], and R ^4
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.

(189) R ³ is a lower alkoxy lower alkyl group, R ⁴ is a group represented by the above [Chemical 27],
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.

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

(191) R ³ represents a lower alkoxy lower alkyl group, and R ⁴ is selected from the group consisting of a lower alkoxy group as a substituent, a halogen atom, a lower alkanoyl group as a substituent and a phenyl lower alkenylcarbonyl group on the phenyl ring. Amino group which may have a lower group, 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, and a group —O—A ₄ —CO—NR ⁴⁰ R
⁴¹ (A ₄ , R ⁴⁰ and R ⁴¹ are the same as above), a lower alkenyloxy group, a nitro group and a phenyl 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. Represents a lower alkenyl group,
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.

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

(193) R ³ represents a lower alkoxy lower alkyl group, R ⁴ represents a lower alkenyl group, 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.

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

(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 those defined above in formula (1) A quinoxaline derivative represented by or a salt thereof.

(196) R ³ represents a phenoxycarbonyl group, R ⁴ represents a cycloalkyl lower alkyl group,
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.

(197) R ³ represents a lower alkoxy lower alkyl group, R ⁴ represents a naphthyl lower alkyl group,
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.

(198) R ³ represents a phenoxycarbonyl group, R ⁴ represents a naphthyl lower alkyl group, 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.

(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 the phenyl ring, 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 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 the phenyl ring, 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.

(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 the phenyl ring, and R ¹ , R ² , The quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as above.

(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, The quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein n and r are the same as described above.

(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 the phenyl ring, and R ¹ , R ² , The quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as above.

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

(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 are the same as those defined above in formula (1) A quinoxaline derivative represented by or a salt thereof.

(206) R ³ represents a phenoxycarbonyl group, R ⁴ represents a phenoxy-substituted lower alkyl group,
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.

(207) R ³ represents a lower alkoxy lower alkyl group, R ⁴ represents a group represented by the above [Chemical Formula 28],
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.

(208) R ³ represents a phenoxycarbonyl group, R ⁴ represents a group represented by the above [Chemical Formula 28], 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.

(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 and
The quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as above.

(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 above), 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.

(211) R ³ represents a lower alkoxy lower alkyl group, and 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 the 2,3-dihydro-1H-indenyl ring. 2,3-dihydro-1H-indenyl group-substituted lower alkyl group which may have a group selected from the group consisting of R ¹ , R ² ,
The quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as above.

(212) A group which is a silyloxy group in which R ³ represents a phenoxycarbonyl group, and R ⁴ has an oxo group as a substituent and a hydroxyl group and a lower alkyl group as a substituent on the 2,3-dihydro-1H-indenyl ring. 2,3-dihydro-1H-indenyl group-substituted lower alkyl group which may have a group selected from the following, wherein R ¹ , R ² , m, n and r are the same as those described above in the general formula (1) The indicated quinoxaline derivative or its salt.

(213) R ³ represents a lower alkoxy lower alkyl group, R ⁴ represents a group represented by the above [Chemical Formula 34],
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.

(214) R ³ represents a phenoxycarbonyl group, R ⁴ represents a group represented by the above [Chemical Formula 34], 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.

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

(217) R ³ represents a lower alkanoyl group-substituted lower alkyl group, and R ⁴ represents a lower alkoxy group as a substituent, a halogen atom, a lower alkanoyl group as a substituent and a phenyl lower alkenylcarbonyl group on the 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 above), a lower alkenyloxy group, a nitro group and a phenyl 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. Represents a lower alkenyl group,
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.

(218) R ³ represents a lower alkoxycarbonyloxy-substituted lower alkyl group, and R ⁴ is a lower alkoxy group as a substituent, a halogen atom, a lower alkanoyl group as a substituent and a phenyl lower alkenylcarbonyl group on the 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, 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, 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, R 3
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.

(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 are the same as those described above. ) The quinoxaline derivative or its salt shown by these.

(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 are the same as those defined above. ) The quinoxaline derivative or its salt shown by these.

(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 those defined above. A 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). ) The quinoxaline derivative or its salt shown by these.

(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 are the same as those described above. A quinoxaline derivative represented by 1) or a salt thereof.

(225) R ³ represents a lower alkanoyl group-substituted 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, 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 a salt thereof.

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

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

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

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

(230) R ³ represents a lower alkoxycarbonyloxy-substituted 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 the same as defined above, or a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(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 are the same as those in the general formula ( A quinoxaline derivative represented by 1) or a salt thereof.

(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 those defined above. A 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 [Chemical Formula 28], and R ¹ , R ² , m, n and r are the same as defined above. A quinoxaline derivative represented by the general formula (1) or a salt thereof.

(234) R ³ represents a lower alkoxycarbonyloxy-substituted lower alkyl group, and R ⁴ represents 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 defined 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 the same as defined above),
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.

(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 the same as above)
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.

(237) R ³ represents a lower alkanoyl group-substituted lower alkyl group, and R ⁴ has an oxo group as a substituent, 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
1H-indenyl group-substituted lower alkyl group is represented by 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.

(238) R ³ represents a lower alkoxycarbonyloxy-substituted lower alkyl group, and R ⁴ represents an oxo group, a hydroxyl group or a lower alkyl group as a substituent on the 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 lower alkyl group substituted with a dihydro-1H-indenyl group, and R ¹ , R ² , m, n and r are the same as defined above.

(239) R ³ represents a lower alkanoyl group-substituted lower alkyl group, R ⁴ represents a group represented by the above [Chemical Formula 34], and R ¹ , R ² , m, n and r are the same as defined above. A quinoxaline derivative represented by the general formula (1) or a salt thereof.

(240) R ³ represents a lower alkoxycarbonyloxy-substituted lower alkyl group, and R ⁴ represents 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 defined above.

(241) R ³ is a benzoyl-substituted lower alkyl group which may have a halogen atom as a substituent on the phenyl ring, R ⁴ is the group represented by the above [Chemical formula 27], and R ¹ and 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.

(242) R ³ is a group —E—NR ⁵² R ⁵³ (E, R
⁵² and R ⁵³ are the same as the above), and R ⁴ is the above
7], 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.

(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 on the phenyl ring as a substituent. , 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-substituted lower alkoxy group, a tetrazolyl group which may have a lower alkyl group as a substituent on the tetrazole ring , Hydroxyl group, group —OA ₄ —CO—NR ⁴⁰ R ⁴¹
(A ₄ , R ⁴⁰ and R ⁴¹ are the same as above), a lower alkenyloxy group, a nitro group and a 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. Represents an alkenyl group, 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.

(244) R ³ is a group —E—NR ⁵² R ⁵³ (E, R
⁵² and R ⁵³ are the same as 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 as a substituent and a phenyl lower alkenylcarbonyl group on the phenyl ring. Sometimes amino group, 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—N—R ⁴⁰ R ⁴¹ (A ₄ , R ⁴⁰ and R ⁴¹ are the same as 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, 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,
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.

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

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

(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, 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.

(250) R ³ is a group —E—NR ⁵² R ⁵³ (E, R
⁵² and R ⁵³ are the same as above), R ⁴ is a naphthyl lower alkyl group, and R ¹ , R ² , m, n and r are the same as 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 phenylthio 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, and R ¹ , R ² , m, n and r are the same as defined above.

(252) R ³ is a group —E—NR ⁵² R ⁵³ (E, R
⁵² and R ⁵³ are the same as described above), 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 ,
The quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as above.

(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 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 R ¹ , R ² , m, n and r are the same as defined above.

(254) R ³ is a group —E—NR ⁵² R ⁵³ (E, R
⁵² and R ⁵³ are the same as above), 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 defined above, or a quinoxaline derivative represented by the general formula (1) or a salt thereof.

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

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

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

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

(260) R ³ is a group —E—NR ⁵² R ⁵³ (E, R
⁵² and R ⁵³ are the same as the above), and R ⁴ is the above
8], 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.

(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 ,
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.

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

(264) R ³ is a group —E—NR ⁵² R ⁵³ (E, R
⁵² and R ⁵³ are the same as above), and R ⁴ is an oxo group as a substituent on the 2,3-dihydro-1H-indenyl ring,
It may have a group selected from the group consisting of 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 lower alkyl group substituted with a 3-dihydro-1H-indenyl group, and R ¹ , R ² , m, n and r are the same as defined above.

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

(266) R ³ is a group —E—NR ⁵² R ⁵³ (E, R
⁵² and R ⁵³ are the same as the above), and R ⁴ is the above [Chemical Formula 3
4], 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.

(267) R ³ represents a group represented by [Chemical Formula 26], R ⁴ represents a group represented by [Chemical Formula 27], 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 a salt thereof.

(268) R ³ represents a group represented by the above [Chemical Formula 26], and R ⁴ represents a lower alkoxy group as a substituent, a halogen atom, a lower alkanoyl group as a substituent and a phenyl lower alkenylcarbonyl group on the phenyl ring. An amino group which may have a group selected from the group consisting of the following, 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, and a group —O—A ₄ — CO-NR ⁴⁰ R ⁴¹ (A ₄ ,
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. , R ¹ , R
² , quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as above.

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

(270) R ³ represents a group represented by the above [Chemical Formula 26], R ⁴ represents a cycloalkyl lower alkyl group,
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.

(271) R ³ represents a group represented by the above [Chemical Formula 26], R ⁴ represents a naphthyl lower alkyl group, 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.

(272) R ³ represents a group represented by the above [Chemical Formula 26], 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 defined above, or a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(273) R ³ represents a group represented by the above [Chemical Formula 26], 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 defined above, or a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(274) R ³ represents a group represented by the above [Chemical Formula 26], 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 defined above, or a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(275) R ³ represents a group represented by the above [Chemical Formula 26], R ⁴ represents a phenoxy-substituted lower alkyl group,
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.

(276) R ³ represents a group represented by the above [formula 26], R ⁴ represents a group represented by the above [formula 28], 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.

(277) R ³ represents a group represented by the above [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 ,
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.

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

(279) R ³ represents a group represented by [Chemical Formula 26], R ⁴ represents a group represented by [Chemical Formula 34], 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 a salt thereof.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

(353) R ¹ represents the definition of the above (1), and R ³
And R ⁴ is the above (141), (142), (167), (168), (19
3), (194), (219), (220), (245), (246) or (26
The quinoxaline derivative represented by the general formula (1) or a salt thereof, which has the definition of 9), and R ² , m, n, and r are the same as defined above.

(354) R ¹ represents the definition of the above (1), R ³
And R ⁴ is (143), (144), (169), (170), (19
5), (196), (221), (222), (247), (248) or (27
(0), 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.

(355) R ¹ represents the definition of the above (1), R ³
And R ⁴ is the above (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 the definition of 1) is shown and R ² , m, n and r are the same as defined above.

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

(357) R ¹ represents the definition of the above (1), and R ³
And R ⁴ is 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, which has the definition of 3), and R ² , m, n and r are the same as defined above.

(358) R ¹ represents the definition of the above (1), and R ³
And R ⁴ is (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 4) is defined and R ² , m, n and r are the same as defined above.

(359) R ¹ represents the definition of the above (1), R ³
And R ⁴ is (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 5) is defined and R ² , m, n and r are the same as defined above.

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

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

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

(363) R ¹ represents the definition of (1) above, R ³
And R ⁴ is (161), (162), (187), (188), (21
3), (214), (239), (240), (265), (266) or (27
The quinoxaline derivative represented by the general formula (1) or a salt thereof, which has the definition of 9), and 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.
(137), (138), (163), (164), (189), (190), (2
15), (216), (241), (242) or (267), wherein m, n and r are the same as defined above, and the 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.
(139), (140), (165), (166), (191), (192), (2
17), (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.

(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.
(141), (142), (167), (168), (193), (194), (2
19), (220), (245), (246) or (269), wherein m, n and r are the same as defined above, and the quinoxaline derivative represented by the general formula (1) or a salt thereof.

(367) R ¹ represents the definition of (2) or (3), R ² represents the definition of (4), and R ³ and R ⁴ represent the above.
(143), (144), (169), (170), (195), (196), (2
21), (222), (247), (248) or (270) is defined, and m, n and r are the same as defined above, and the 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.
(145), (146), (171), (172), (197), (198), (2
23), (224), (249), (250) or (271), wherein m, n and r are the same as defined above, and the 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.
(147), (148), (173), (174), (199), (200), (2
25), (226), (251), (252) or (272) is defined, and m, n and r are the same as defined above, and the 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.
(149), (150), (175), (176), (201), (202), (2
27), (228), (253), (254) or (273) is defined, and m, n and r are the same as defined above, and the 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.
(151), (152), (177), (178), (203), (204), (2
29), (230), (255), (256) or (274) is defined, and m, n and r are the same as defined above, and the 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.
(153), (154), (179), (180), (205), (206), (2
31), (232), (257), (258) or (275) is defined, and m, n and r are the same as defined above, and the quinoxaline derivative represented by the general formula (1) or a salt thereof.

(373) R¹Indicates the definition of (2) or (3) above.
Then R²Is the definition of (4) above, and R ³And R^FourIs the above
(155), (156), (181), (182), (207), (208), (2
33), (234), (259), (260) or (276)
Where m, n and r are represented by the general formula (1) which is the same as above.
A quinoxaline derivative 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.
(157), (158), (183), (184), (209), (210), (2
35), (236), (261), (262) or (277) is defined, and m, n and r are the same as defined above, and the 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.
(159), (160), (185), (186), (211), (212), (2
37), (238), (263), (264) or (278) is defined, and m, n and r are the same as defined above, and the 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.
(161), (162), (187), (188), (213), (214), (2
39), (240), (265), (266) or (279) is defined and m, n and r are the same as defined above, and the 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.
(137), (138), (163), (164), (189), (190), (2
15), (216), (241), (242) or (267), wherein m, n and r are the same as defined above, and the 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.
(139), (140), (165), (166), (191), (192), (2
17), (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.

(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.
(141), (142), (167), (168), (193), (194), (2
19), (220), (245), (246) or (269), wherein m, n and r are the same as defined above, and the 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.
(143), (144), (169), (170), (195), (196), (2
21), (222), (247), (248) or (270) is defined, and m, n and r are the same as defined above, and the 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.
(145), (146), (171), (172), (197), (198), (2
23), (224), (249), (250) or (271), wherein m, n and r are the same as defined above, and the 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.
(147), (148), (173), (174), (199), (200), (2
25), (226), (251), (252) or (272) is defined, and m, n and r are the same as defined above, and the 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.
(149), (150), (175), (176), (201), (202), (2
27), (228), (253), (254) or (273) is defined, and m, n and r are the same as defined above, and the quinoxaline derivative represented by the general formula (1) or a salt thereof.

(384) R ¹ represents the definition of (2) or (3), R ² represents the definition of (5), and R ³ and R ⁴ represent the above.
(151), (152), (177), (178), (203), (204), (2
29), (230), (255), (256) or (274) is defined, and m, n and r are the same as defined above, and the 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.
(153), (154), (179), (180), (205), (206), (2
31), (232), (257), (258) or (275) is defined, and m, n and r are the same as defined above, and the 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.
(155), (156), (181), (182), (207), (208), (2
33), (234), (259), (260) or (276) is defined and m, n and r are the same as defined above, and the 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.
(157), (158), (183), (184), (209), (210), (2
35), (236), (261), (262) or (277) is defined, and m, n and r are the same as defined above, and the 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.
(159), (160), (185), (186), (211), (212), (2
37), (238), (263), (264) or (278) is defined, and m, n and r are the same as defined above, and the 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.
(161), (162), (187), (188), (213), (214), (2
39), (240), (265), (266) or (279) is defined and m, n and r are the same as defined above, and the 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.
(137), (138), (163), (164), (189), (190), (2
15), (216), (241), (242) or (267), wherein m, n and r are the same as defined above, and the 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.
(139), (140), (165), (166), (191), (192), (2
17), (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.
(141), (142), (167), (168), (193), (194), (2
19), (220), (245), (246) or (269), wherein m, n and r are the same as defined above, and the 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.
(143), (144), (169), (170), (195), (196), (2
21), (222), (247), (248) or (270) is defined, and m, n and r are the same as defined above, and the 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.
(145), (146), (171), (172), (197), (198), (2
23), (224), (249), (250) or (271), wherein m, n and r are the same as defined above, and the 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.
(147), (148), (173), (174), (199), (200), (2
25), (226), (251), (252) or (272) is defined, and m, n and r are the same as defined above, and the quinoxaline derivative represented by the general formula (1) or a salt thereof.

(396) R¹Indicates the definition of (2) or (3) above.
Then R²Is the definition of (6) above, and R ³And R^FourIs the above
(149), (150), (175), (176), (201), (202), (2
27), (228), (253), (254) or (273)
Where m, n and r are represented by the general formula (1) which is the same as above.
A quinoxaline derivative 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.
(151), (152), (177), (178), (203), (204), (2
29), (230), (255), (256) or (274) is defined, and m, n and r are the same as defined above, and the 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.
(153), (154), (179), (180), (205), (206), (2
31), (232), (257), (258) or (275) is defined, and m, n and r are the same as defined above, and the 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.
(155), (156), (181), (182), (207), (208), (2
33), (234), (259), (260) or (276) is defined and m, n and r are the same as defined above, and the 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.
(157), (158), (183), (184), (209), (210), (2
35), (236), (261), (262) or (277) is defined, and m, n and r are the same as defined above, and the 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.
(159), (160), (185), (186), (211), (212), (2
37), (238), (263), (264) or (278) is defined, and m, n and r are the same as defined above, and the 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.
(161), (162), (187), (188), (213), (214), (2
39), (240), (265), (266) or (279) is defined and m, n and r are the same as defined above, and the 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.
(137), (138), (163), (164), (189), (190), (2
15), (216), (241), (242) or (267), wherein m, n and r are the same as defined above, and the 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.
(139), (140), (165), (166), (191), (192), (2
17), (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.

(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.
(141), (142), (167), (168), (193), (194), (2
19), (220), (245), (246) or (269), wherein m, n and r are the same as defined above, and the 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.
(143), (144), (169), (170), (195), (196), (2
21), (222), (247), (248) or (270) is defined, and m, n and r are the same as defined above, and the 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.
(145), (146), (171), (172), (197), (198), (2
23), (224), (249), (250) or (271), wherein m, n and r are the same as defined above, and the 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.
(147), (148), (173), (174), (199), (200), (2
25), (226), (251), (252) or (272) is defined, and m, n and r are the same as defined above, and the 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.
(149), (150), (175), (176), (201), (202), (2
27), (228), (253), (254) or (273) is defined, and m, n and r are the same as defined above, and the 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.
(151), (152), (177), (178), (203), (204), (2
29), (230), (255), (256) or (274) is defined, and m, n and r are the same as defined above, and the 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.
(153), (154), (179), (180), (205), (206), (2
31), (232), (257), (258) or (275) is defined, and m, n and r are the same as defined above, and the quinoxaline derivative represented by the general formula (1) or a salt thereof.

(412) R ¹ represents the definition of (2) or (3), R ² represents the definition of (7), and R ³ and R ⁴ represent the above.
(155), (156), (181), (182), (207), (208), (2
33), (234), (259), (260) or (276) is defined and m, n and r are the same as defined above, and the 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.
(157), (158), (183), (184), (209), (210), (2
35), (236), (261), (262) or (277) is defined, and m, n and r are the same as defined above, and the 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.
(159), (160), (185), (186), (211), (212), (2
37), (238), (263), (264) or (278) is defined, and m, n and r are the same as defined above, and the 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.
(161), (162), (187), (188), (213), (214), (2
39), (240), (265), (266) or (279) is defined and m, n and r are the same as defined above, and the 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.
(137), (138), (163), (164), (189), (190), (2
15), (216), (241), (242) or (267), wherein m, n and r are the same as defined above, and the 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.
(139), (140), (165), (166), (191), (192), (2
17), (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.

(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.
(141), (142), (167), (168), (193), (194), (2
19), (220), (245), (246) or (269), wherein m, n and r are the same as defined above, and the quinoxaline derivative represented by the general formula (1) or a salt thereof.

(419) R¹Indicates the definition of (2) or (3) above.
Then R²Is the definition of (8) above, and R ³And R^FourIs the above
(143), (144), (169), (170), (195), (196), (2
21), (222), (247), (248) or (270)
Where m, n and r are represented by the general formula (1) which is the same as above.
A quinoxaline derivative 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.
(145), (146), (171), (172), (197), (198), (2
23), (224), (249), (250) or (271), wherein m, n and r are the same as defined above, and the 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.
(147), (148), (173), (174), (199), (200), (2
25), (226), (251), (252) or (272) is defined, and m, n and r are the same as defined above, and the 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.
(149), (150), (175), (176), (201), (202), (2
27), (228), (253), (254) or (273) is defined, and m, n and r are the same as defined above, and the 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.
(151), (152), (177), (178), (203), (204), (2
29), (230), (255), (256) or (274) is defined, and m, n and r are the same as defined above, and the 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.
(153), (154), (179), (180), (205), (206), (2
31), (232), (257), (258) or (275) is defined, and m, n and r are the same as defined above, and the 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.
(155), (156), (181), (182), (207), (208), (2
33), (234), (259), (260) or (276) is defined and m, n and r are the same as defined above, and the 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.
(157), (158), (183), (184), (209), (210), (2
35), (236), (261), (262) or (277) is defined, and m, n and r are the same as defined above, and the 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.
(159), (160), (185), (186), (211), (212), (2
37), (238), (263), (264) or (278) is defined, and m, n and r are the same as defined above, and the 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.
(161), (162), (187), (188), (213), (214), (2
39), (240), (265), (266) or (279) is defined and m, n and r are the same as defined above, and the quinoxaline derivative represented by the general formula (1) or a salt thereof.

(429) R ¹ is the above (134), (135) or (13
6), R ² represents the definition of (4) above, and R ³
And R ⁴ is the above (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, a quinoxaline derivative represented by the general formula (1) or a salt thereof.

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

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

(432) R ¹ is the above (134), (135) or (13)
6), R ² represents the definition of (4) above, and R ³
And R ⁴ is (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, a quinoxaline derivative represented by the general formula (1) or a salt thereof.

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

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

(435) R ¹ is the above (134), (135) or (13)
6), R ² represents the definition of (4) above, and R ³
And R ⁴ is 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 3) is defined and m, n and r are the same as defined above.

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

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

(438) R ¹ is the above (134), (135) or (13)
6), R ² represents the definition of (4) above, and R ³
And R ⁴ is (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 6) is defined and m, n and r are the same as defined above.

(439) R ¹ is the above (134), (135) or (13
6), R ² represents the definition of (4) above, and R ³
And R ⁴ is the above (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, a quinoxaline derivative represented by the general formula (1) or a salt thereof.

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

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

(442) R ¹ is the above (134), (135) or (13)
6), R ² represents the definition of (5) above, and R ³
And R ⁴ is the above (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, a quinoxaline derivative represented by the general formula (1) or a salt thereof.

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

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

(445) R ¹ is the above (134), (135) or (13)
6), R ² represents the definition of (5) above, and R ³
And R ⁴ is (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, a quinoxaline derivative represented by the general formula (1) or a salt thereof.

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

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

(448) R ¹ is the above (134), (135) or (13)
6), R ² represents the definition of (5) above, and R ³
And R ⁴ is 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 3) is defined and m, n and r are the same as defined above.

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

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

(451) R ¹ is the above (134), (135) or (13)
6), R ² represents the definition of (5) above, and R ³
And R ⁴ is (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 6) is defined and m, n and r are the same as defined above.

(452) R ¹ is the above (134), (135) or (13)
6), R ² represents the definition of (5) above, and R ³
And R ⁴ is the above (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, a quinoxaline derivative represented by the general formula (1) or a salt thereof.

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

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

(455) R ¹ is the above (134), (135) or (13)
6), R ² is the definition of (6) above, R ³
And R ⁴ is the above (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, a quinoxaline derivative represented by the general formula (1) or a salt thereof.

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

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

(458) R ¹ is the above (134), (135) or (13
6), R ² is the definition of (6) above, R ³
And R ⁴ is (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, a quinoxaline derivative represented by the general formula (1) or a salt thereof.

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

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

(461) R ¹ is the above (134), (135) or (13)
6), R ² is the definition of (6) above, R ³
And R ⁴ is 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 3) is defined and m, n and r are the same as defined above.

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

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

(464) R ¹ is the above (134), (135) or (13)
6), R ² is the definition of (6) above, R ³
And R ⁴ is (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 6) is defined and m, n and r are the same as defined above.

(465) R ¹ is the above (134), (135) or (13
6), R ² is the definition of (6) above, R ³
And R ⁴ is the above (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, a quinoxaline derivative represented by the general formula (1) or a salt thereof.

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

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

(468) R ¹ is the above (134), (135) or (13
6), R ² represents the definition of (7) above, R ³
And R ⁴ is the above (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, a quinoxaline derivative represented by the general formula (1) or a salt thereof.

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

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

(471) R ¹ is the above (134), (135) or (13)
6), R ² represents the definition of (7) above, R ³
And R ⁴ is (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, a quinoxaline derivative represented by the general formula (1) or a salt thereof.

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

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

(474) R ¹ is the above (134), (135) or (13
6), R ² represents the definition of (7) above, R ³
And R ⁴ is 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 3) is defined and m, n and r are the same as defined above.

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

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

(477) R ¹ is the above (134), (135) or (13
6), R ² represents the definition of (7) above, R ³
And R ⁴ is (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 6) is defined and m, n and r are the same as defined above.

(478) R ¹ is the above (134), (135) or (13
6), R ² represents the definition of (7) above, R ³
And R ⁴ is the above (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, a quinoxaline derivative represented by the general formula (1) or a salt thereof.

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

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

(481) R ¹ is the above (134), (135) or (13
6), R ² represents the definition of (8) above, and R ³
And R ⁴ is the above (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, a quinoxaline derivative represented by the general formula (1) or a salt thereof.

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

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

(484) R ¹ is the above (134), (135) or (13)
6), R ² represents the definition of (8) above, and R ³
And R ⁴ is (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, a quinoxaline derivative represented by the general formula (1) or a salt thereof.

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

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

(487) R ¹ is the above (134), (135) or (13)
6), R ² represents the definition of (8) above, and R ³
And R ⁴ is 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 3) is defined and m, n and r are the same as defined above.

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

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

(490) R ¹ is the above (134), (135) or (13)
6), R ² represents the definition of (8) above, and R ³
And R ⁴ is (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 6) is defined and m, n and r are the same as defined above.

(491) R ¹ is the above (134), (135) or (13)
6), R ² represents the definition of (8) above, and R ³
And R ⁴ is the above (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, a quinoxaline derivative represented by the general formula (1) or a salt thereof.

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

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

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

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

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

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

(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 the same 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 ,
The quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein m, n and r are the same as above.

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

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

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

(503) 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 alkyl group or a lower alkanoyloxy-substituted lower alkyl group. A lower alkoxycarbonyl group or a lower alkoxycarbonyloxy-substituted lower alkyl group, R ⁴ is a group represented by the above [Chemical 27]; a lower alkoxy group as a substituent on the phenyl ring, a halogen atom, a lower alkanoyl group as a substituent And an amino group which may have a group selected from the group consisting of a phenyl lower alkenylcarbonyl group, 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, 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,
Together with the nitrogen atom to which they are bound, they may be bound to each other via other nitrogen atom or oxygen atom or not 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; naphthyl Lower alkyl group; phenylthio-substituted lower alkyl group that may have a lower alkoxy group as a substituent on the phenyl ring; phenylsulfinyl-substituted lower alkyl group that 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 shall form the group = O, the 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-
2,3-dihydro-1H-indenyl group-substituted lower alkyl group which may have 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 on the 1H-indenyl ring. Wherein m, n and r are the same as defined above, 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 Group; phenoxycarbonyl group; lower alkanoyl group substituted lower alkyl group; benzoyl substituted lower alkyl group which may have a halogen atom as a substituent on the phenyl ring; group -E-R ⁵² R ⁵³ (R ⁵² and R ⁵³ are The same or different, each represents a hydrogen atom, a lower alkyl group, a lower alkoxycarbonyl group or a phenyl group, and R ⁵² and R ⁵³ are bonded to each other with the nitrogen atom to which they are bonded via another nitrogen atom or an oxygen atom or not 5 members or 6
You may form the saturated heterocyclic ring of a member ring. E is a lower alkylene group, a group -C (= O)-or a group -C (= O) -A- (A
Represents a lower alkylene group). Or a group represents a group represented by [Chemical Formula 26], and R ⁴ represents a group represented by the above [Chemical Formula 27]; a lower alkoxy group, a halogen atom, a lower alkanoyl group and a phenyl group as a substituent on the phenyl ring. An amino group which may have a group selected from the group consisting of lower alkenylcarbonyl groups, 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, and a group -O. _{^{-A 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,
Together with the nitrogen atom to which they are bound, they may be bound to each other via other nitrogen atom or oxygen atom or not 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; naphthyl Lower alkyl group; phenylthio-substituted lower alkyl group that may have a lower alkoxy group as a substituent on the phenyl ring; phenylsulfinyl-substituted lower alkyl group that 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: -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 alkyl group. R ⁴⁴ represents a phenyl group which may have a lower alkoxy group as a substituent on the phenyl ring); and a substituent on the 2,3-dihydro-1H-indenyl ring. 2,3-dihydro-1H-indenyl group-substituted lower alkyl group which 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, or represented by the above [Chemical Formula 34] General formula (1) in which m, n and r are the same as those described above.
A quinoxaline derivative represented by 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 bonded 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 general formula (1) or a salt thereof, which is the same as above.

(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
8] or a group represented by the above [Chemical Formula 34], 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.

(507) R¹Represents a hydrogen atom, R²Is hydrogen
Atoms, phenyl groups, morpholino-substituted lower alkyl groups or
R represents an imidazolyl-substituted lower alkyl group, R³Is hydrogen
Child, lower alkyl group, lower alkanoyloxy substituted lower
Alkyl group, lower alkoxycarbonyl group or lower alkyl
Coxycarbonyloxy represents a lower alkyl group, R
^FourIs a group represented by the above [Chemical 27]; substituted on the phenyl ring
As a lower alkoxy group, a halogen atom, a substituent
Lower alkanoyl group and phenyl lower alkenyl
Amine which may have a group selected from the group consisting of bonyl groups.
Group, lower alkoxy group, substituted lower alkoxy group, tetra
Having a lower alkyl group as a substituent on the sol ring
With tetrazolyl group, hydroxyl group, group-OA_Four-CO-
NR⁴⁰R⁴¹(A_FourRepresents a lower alkylene group. R⁴⁰as well as
R⁴¹Are the same or different and each represents a hydrogen atom or a lower alkyl group.
Show. Also R⁴⁰And R⁴¹Is the nitrogen atom to which they bind
With or through other nitrogen or oxygen atoms
Without forming a 5- or 6-membered saturated heterocycle
May be done. ), Lower alkenyloxy group, nitro group
And a lower group which may have a halogen atom as a substituent
A group which may have a group selected from the group consisting of alkyl groups
Phenyl lower alkenyl group; alkenyl group; cycloalkyl
Ru lower alkyl group; naphthyl lower alkyl group; phenyl
Having a lower alkoxy group as a substituent on the ring
Phenylthio-substituted lower alkyl group; placed on the phenyl ring
Pheny that may have a lower alkoxy group as a substituent
Rusulfinyl-substituted lower alkyl group; placed on the phenyl ring
Pheny that may have a lower alkoxy group as a substituent
Sulfonyl substituted lower alkyl group; phenoxy substituted lower
Alkyl group; group -A_Five-CR⁴²R⁴³R⁴⁴(A in the formula_FiveIs low
Indicates a secondary alkylene group. R ⁴²And R⁴³Are together together
= O, group = N-OH or lower alkylenedioxy group
Shall be achieved. R⁴⁴As 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 group as a substituent.
A group selected from the group consisting of silyloxy groups having a rualkyl group
2,3-dihydro-1H-indeni which may have
Represents a lower alkyl group substituted with a ru group, m, n and r are as described above.
The same quinoxaline derivative represented by the general formula (1)
Or its salt.

(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;
Lower alkoxy lower alkyl group; phenoxycarbonyl group; lower alkanoyl group substituted lower alkyl group; 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 each 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 together with the nitrogen atom to which they are bonded via another nitrogen atom or an oxygen atom to form a 5- or 6-membered saturated heterocycle. E represents a lower alkylene group, a group -C (= O)-or a group -C (= O) -A- (A is a lower alkylene group). Or a group represents a group represented by [Chemical Formula 26], and R ⁴ represents a group represented by the above [Chemical Formula 27]; a lower alkoxy group, a halogen atom, a lower alkanoyl group and a phenyl group as a substituent on the phenyl ring. An amino group which may have a group selected from the group consisting of lower alkenylcarbonyl groups, 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, and 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. Further, R ⁴⁰ and R ⁴¹ may be bonded to each other with a nitrogen atom to which they are bonded via another nitrogen atom or an oxygen atom or not 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; naphthyl Lower alkyl group; phenylthio-substituted lower alkyl group that may have a lower alkoxy group as a substituent on the phenyl ring; phenylsulfinyl-substituted lower alkyl group that 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]; group -A ₅ -C
R ⁴² R ⁴³ R ⁴⁴ (wherein A ₅ represents a lower alkylene group.
⁴² and R ⁴³ shall 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. ); 2,3-Dihydro-
2,3-dihydro-1H-indenyl group-substituted lower alkyl group which may have 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 on the 1H-indenyl ring. Alternatively, a quinoxaline derivative represented by the general formula (1) or a salt thereof, which represents the group represented by the above [Chemical Formula 34], and m, n and r are the same as described 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 (which may have a lower alkoxy group as a substituent on this heterocycle) formed by bonding with the nitrogen atom to which they are bonded. , M, n and r are the same as defined above, or 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, 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.

(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, R ⁴ is a group represented by the above [Chemical Formula 27]; a lower alkoxy group or a halogen atom 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 as a substituent, a lower alkoxy group, a substituted lower alkoxy group, and a lower alkyl group which has a substituent on the tetrazole ring. 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 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 that may have a lower alkoxy group as a substituent on the phenyl ring; phenylsulfinyl-substituted lower alkyl group that may have a lower alkoxy group as a substituent on the phenyl ring; phenyl ring A phenylsulfonyl-substituted lower alkyl group which may have a lower alkoxy group as a substituent on the above; a phenoxy-substituted lower alkyl group; a group -A
_5- CR ⁴² R ⁴³ R ⁴⁴ (In the formula, 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, it shall form 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 a 2,3-dihydro-which may have 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 on the 2,3-dihydro-1H-indenyl ring. A quinoxaline derivative represented by the general formula (1) or a salt thereof, which represents a 1H-indenyl group-substituted lower alkyl group, and m, n and r are the same as described 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; phenyl A benzoyl-substituted lower alkyl group which may have a halogen atom as a substituent on the ring; group -E-R 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 Or a phenyl group, R ⁵² and R ⁵³ are bonded together with the nitrogen atom to which they are bonded via another nitrogen atom or an oxygen atom to each other to form a 5- or 6-membered saturated heterocycle. E may be a lower alkylene group, a group -C (= O)-or a group -C (= O) -A-.
(A is a lower alkylene group). ) Or state [Chemical 2
6], wherein R ⁴ is a group represented by the above [Chemical 27]; a group consisting of a lower alkoxy group as a substituent, a halogen atom, a lower alkanoyl group as a substituent and a phenyl lower alkenylcarbonyl group on the phenyl ring. An amino group which may have a selected group, 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,
Hydroxyl group, 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. R ⁴⁰ and R ⁴¹
May be bonded to each other with a nitrogen atom to which they are bonded via another nitrogen atom or an oxygen atom or not 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; naphthyl Lower alkyl group; phenylthio-substituted lower alkyl group that may have a lower alkoxy group as a substituent on the phenyl ring; phenylsulfinyl-substituted lower alkyl group that 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 group -A ₅ -CR ⁴² R ⁴³ R ⁴⁴ (wherein A is 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 1,3-dihydro-1H-indenyl group-substituted lower alkyl which may have 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 on the -1H-indenyl ring. A quinoxaline derivative represented by the general formula (1) or a salt thereof, which represents a group or a group represented by the above [Chemical Formula 34], and m, n and r are the same as 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 1,2,3,4-tetrahydroisoquinolyl group formed by bonding with a nitrogen atom to which they are bonded. (This heterocycle may have a lower alkoxy group as a substituent), m,
The quinoxaline derivative represented by the general formula (1) or a salt thereof, wherein n and r are the same as described above.

(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 represents a hydrogen atom, a phenyl group, a morpholino-substituted lower alkyl group or an imidazolyl-substituted lower alkyl group, and R ³
Is 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 is a group represented by the above [Chemical Formula 28] or a group represented by the above [Chemical Formula 34]. Wherein m, n and r are the same as defined above, 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 represents a hydrogen atom, a phenyl group, a morpholino-substituted lower alkyl group or an imidazolyl-substituted lower alkyl group, and R ³
Is 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 27]; substituted on the phenyl ring 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-substituted lower alkoxy group, a substituent on the tetrazole ring May have a lower alkyl group as a tetrazolyl group, hydroxyl group, 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. R ⁴⁰ and R ⁴¹ are the nitrogen to which they are bonded. Atoms may be bonded to each other to form a 5- or 6-membered saturated heterocyclic ring with or without other nitrogen atom or oxygen atom), 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 that may have a lower alkoxy group as a substituent on the phenyl ring; phenylsulfinyl substitution that 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 on the phenyl ring; a lower alkyl group a phenoxy-substituted lower alkyl group; group -A ₅ -CR ⁴² R ⁴³ R
⁴⁴ (wherein A ₅ represents a lower alkylene group. R ⁴² and R ⁴³
Shall 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 a 2,3-dihydro-which may have 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 on the 2,3-dihydro-1H-indenyl ring.
1H-indenyl group-substituted lower alkyl group, m, n
And r are the same as described above, 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 represents a hydrogen atom, a phenyl group, a morpholino-substituted lower alkyl group or an imidazolyl-substituted lower alkyl group, and 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; Group -E-R ⁵² R
⁵³ (R ⁵² and R ⁵³ are the same or different and each represents a hydrogen atom, a lower alkyl group, a lower alkoxycarbonyl group or a phenyl group. R ⁵² and R ⁵³ are a nitrogen atom to which these are bonded, other nitrogen atoms or oxygen. They may be bonded to each other with or without an atom to form a 5- or 6-membered saturated heterocycle, wherein E is a lower alkylene group or a group -C (=
O)-or a group -C (= O) -A- (A is a lower alkylene group). Or a group represents a group represented by [Chemical Formula 26], and R ⁴ represents a group represented by the above [Chemical Formula 27]; a lower alkoxy group, a halogen atom, a lower alkanoyl group and a phenyl group as a substituent on the 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 represents a hydrogen atom or a lower alkyl group. Further, R ⁴⁰ and R ⁴¹ may be bonded to each other with a nitrogen atom to which they are bonded via another nitrogen atom or an oxygen atom or not 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; naphthyl Lower alkyl group; phenylthio-substituted lower alkyl group that may have a lower alkoxy group as a substituent on the phenyl ring; phenylsulfinyl-substituted lower alkyl group that 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}} ( wherein A ₅ are a lower alkylene group .R ⁴² and R ⁴³ together group = O, group = N-O
H or a lower alkylenedioxy group shall be 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 substituted lower which may have 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 on the dihydro-1H-indenyl ring A quinoxaline derivative represented by the general formula (1) or a salt thereof, which represents an alkyl group or a group represented by the above [Chemical Formula 34], and m, n and r are the same as 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 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 with the nitrogen atom to which they are bonded (which may have a lower alkoxy group as a substituent on this heterocycle) ) And m, n and r are the same as defined above, or a quinoxaline derivative represented by the general formula (1) or a salt thereof.

(518) The saturated or unsaturated heterocyclic moiety of the saturated or unsaturated heterocycle-substituted lower alkyl group represented by [Formula 29] in the group represented by [Formula 28] 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,
The above (502), (504), (506), (508), (510), (51 which is a 1,2,3,4-tetrazolyl or oxazolyl group.
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 moiety of the saturated or unsaturated heterocyclic-substituted lower alkyl group represented by [Chemical 29] in the group represented by [Chemical 28] is a benzofuryl or oxazolyl group. (502), (504), (506),
(508), (510), (512), (514) and the quinoxaline derivative represented by the general formula (1) described in (516) or a salt thereof.

(520) The saturated or unsaturated heterocyclic moiety of the saturated or unsaturated heterocycle-substituted lower alkenyl group represented by [Formula 35] in the group represented by [Formula 34] is benzofuryl, benzothienyl or carbostyryl. , 3,4-dihydrocarbostyryl, 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) The saturated or unsaturated heterocyclic-substituted lower alkenyl group represented by [Chemical Formula 35] in the group represented by [Chemical Formula 34] in which the saturated or unsaturated heterocyclic moiety is a benzofuryl group. ), (504), (506), (508), (510)
, (512), (514) and (516), and a 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- A quinoxaline derivative selected from the group consisting of 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.
Are included, 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 0 at the same time, and a compound in which m is 1 and n is 0 is particularly preferable.

The heterocyclic group of the group represented by the above [Chemical Formula 29] is 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 group and an imidazo [1.2-a] pyridyl group are particularly preferable.

The heterocyclic group of the group represented by the above [Chemical Formula 31] includes 1,2,3,4-tetrazolyl, thiazolyl,
Pyridyl, oxazolyl, 1,2,3,5-oxathiadiazolyl, 1,3,4-triazolyl, 1,2,4-
Particularly preferred are oxadiazolyl, 1,2,4-triazinyl, imidazolyl, 1,3,4-oxadiazolyl, pyrimidinyl, 1,2,3,4-tetrazolyl group and the like.

The heterocyclic group of the group represented by the above [Chemical Formula 33] includes thiazolyl, 1,2,3,4-tetrazolyl,
A thiazolidinyl group and the like are particularly preferable.

The heterocyclic group of the group represented by the above [Chemical Formula 35] is benzofuryl, benzothiazolyl, carbostyryl, 3,4-dihydrocarbostyryl, 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 preferable.

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 the method shown below.

[0641]

Embedded image

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

In the mixed acid anhydride method shown in (a) above, the mixed acid anhydride used is obtained by a conventional Jotten-Baumann reaction, which is usually reacted with the amine (3) without isolation. Thus, the compound of the general formula (1) is produced. The Schotten-Baumann reaction is carried out in the presence of a basic compound. As the basic compound used, a compound commonly used in the Schotten-Baumann reaction is used, and 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 hydrogen carbonate, and sodium hydrogen carbonate. The reaction is about -20 to 100
C., preferably at 0-50 C. for about 5 minutes to 10 hours,
It is preferably carried out for about 5 minutes to 2 hours. The reaction between the obtained mixed acid anhydride and the amine (3) is about -20 to 15
It 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. 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 and dichloroethane, 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, 1,1,
It 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 halocarboxylic acid alkyl ester used in the production of the above mixed acid anhydride include methyl chloroformate, methyl bromoformate, ethyl chloroformate, ethyl bromoformate, isobutyl chloroformate and the like. The halocarboxylic acid alkyl ester is usually used in at least an equimolar amount, preferably about 1 to 1.5 times the molar amount of the amine (3). The amount of the amine (3) used is usually at least an equimolar amount, preferably about 1 to 1.5 times the molar amount of the carboxylic acid (2).

In the active ester method shown in (b) above, for example, in the case of using N-hydroxysuccinimide ester, for example, in the presence or absence of a basic compound in a suitable solvent that does not affect the reaction. Done below. In addition, a condensing agent such as dicyclohexylcarbodiimide, carbonyldiimidazole, 1-ethyl-3- (3'-dimethylaminopropyl) carbodiimide or the like 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,
It is also possible to use carboxylic acid alkali metal salts such as lithium benzoate and cesium acetate, and alkali metal halide salts such as potassium fluoride and cesium fluoride. 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, Examples thereof include esters such as methyl acetate and ethyl acetate, aprotic polar solvents such as N, N-dimethylformamide, dimethylsulfoxide, and hexamethylphosphoric triamide, and mixed solvents thereof. The reaction is usually 0 to 150 ° C, preferably 10 to 100 ° C.
Then, it will be finished in 5 to 30 hours. The ratio of the amine (3) to the N-hydroxysuccinimide ester used is usually at least equimolar, preferably equimolar to 2 times the molar amount of the compound (2).

The amine (3) and the carboxylic acid (2) were combined with triphenylphosphine, triphenylphosphine-2,2'-dipyridyl disulfide, diethyl chlorophosphate, diphenylphosphinyl chloride, phenyl N-phenylphosphoramide. Compound (1) can also be obtained by reacting a phosphorus compound such as chloridate, diethyl cyanophosphate, and bis (2-oxo-3-oxazolidinyl) phosphinic chloride in the presence of a condensing agent. 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, for example, pyridine, acetone, acetonitrile and the like, or a mixed solvent of two or more of the above solvents. The reaction is usually performed at about -20 to 150 ° C, preferably at about 0 to 100 ° C, and generally the reaction is completed in 5 minutes to 30 hours. The amount of the condensing agent and the amine (3) used is 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 carried out in the presence or absence of a catalyst. As the solvent used here, 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 with respect to the amine (3).
It is preferable to use a 0-fold molar amount, preferably a 2- to 6-fold molar amount. The carboxylic acid (2) is usually used in an amount of at least about equimolar to the amine (3), preferably about equimolar to 2 times the molar amount. The reaction is usually carried out at about 0 to 150 ° C., preferably at room temperature to about 100 ° C., and generally the reaction is completed in about 1 to 10 hours.

When the method of reacting a carboxylic acid halide with an amine (3) shown in (d) above is adopted, the reaction is carried out in the presence of a dehydrohalogenating agent in a suitable solvent. As the dehydrohalogenating agent, a usual basic compound is used. A wide variety of known basic compounds can be used, and examples thereof include sodium hydroxide, potassium hydroxide, sodium hydride and potassium hydride, in addition to the basic compounds used in the Schotten-Baumann reaction. As the solvent, other than 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 and the amine (3) to be used is not particularly limited and may be appropriately selected within a wide range, but the latter is usually at least equimolar to the former, preferably equimolar to 5
It is preferable to use a double molar amount. The reaction is usually -20 to
About 180 ° C., preferably about 0-150 ° 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 in the absence of a solvent or in the presence of a solvent. As the solvent, any solvent which does not adversely influence the reaction can be used, for example, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as chloroform, methylene chloride and carbon tetrachloride, dioxane and tetrahydrofuran. , Ethers such as diethyl ether, dimethylformamide, dimethylsulfoxide, and the like. As the halogenating agent, an ordinary halogenating agent that changes a hydroxyl group of a carboxy group into a halogen can be used, and examples thereof include thionyl chloride, phosphorus oxychloride, phosphorus oxybromide, phosphorus pentachloride, phosphorus pentabromide and the like. . The use ratio of the carboxylic acid (2) and the halogenating agent 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 amount with respect to the former, or in the solvent. When carrying out the reaction, the latter is usually at least equimolar to the former,
Preferably, a 2- to 4-fold molar amount is used. Although the reaction temperature and the reaction time are not particularly limited, the reaction is usually performed at room temperature to about 100 ° C., preferably 50 to 80 ° C. for about 30 minutes to 6 hours.

When the above-mentioned method of reacting the ester of carboxylic acid (2) and lower alcohol with amine (3) is adopted, the reaction is carried out in a suitable solvent or without solvent. As the solvent used here, 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 in an amount of at least equimolar, preferably equimolar to 15 times the molar amount of 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 120 ° C in about 1 to 20 hours.

[0650]

[Chemical 38]

[Wherein R ¹ , R ² , r, m and n are the same as defined above]. X represents a halogen atom. R ^3a represents a hydrogen atom, a lower alkyl group, a phenyl lower alkoxycarbonyl group, a lower alkanoyloxy-substituted lower alkyl group, a lower alkanoyl group, a lower alkoxycarbonyl group, a lower alkoxy lower alkyl group, a phenoxycarbonyl group, a 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 -E-R ⁵² R ⁵³ (R ⁵² and R ⁵³ are
The same or different, a hydrogen atom, a lower alkyl group, a lower alkoxycarbonyl group or a phenyl group is shown. R ⁵² and R
⁵³ may be bonded to each other with the nitrogen atom to which they are bonded via another nitrogen atom or an oxygen atom, or may be bonded to each other to form a 5- or 6-membered saturated heterocycle. E is a lower alkylene group, a group -C (= O)-or a group -C (=
O) -A- (A is a lower alkylene group). ), The group represented by [Chemical Formula 26], the group represented by [Chemical Formula 27], a lower alkoxy group as a substituent on the phenyl ring, a halogen atom, a lower alkanoyl group as a substituent, and a phenyl lower alkenylcarbonyl group. 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 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, alkenyl group, cycloalkyl lower alkyl group, naphthyl lower alkyl group, on the phenyl ring A phenylthio-substituted lower alkyl group that may have a lower alkoxy group as a substituent, a phenylsulfinyl-substituted lower alkyl group that may have a lower alkoxy group as a substituent on the phenyl ring, and a lower alkoxy group as a substituent on the 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 (in the formula, A ₅ , R ⁴² , R ⁴³ and R ⁴⁴ are the same as above), an oxo group, a hydroxyl group and a substituent on the 2,3-dihydro-1H-indenyl ring. A 2,3-dihydro-1H-indenyl group-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 group or a group represented by the above [Chemical Formula 34] is shown. R ^3b represents the above R ^3a other than a hydrogen atom. R ^3c and R ^3d each represent a hydrogen atom or a lower alkyl group. The reaction between the compound of general formula (1a) and the compound of general formula (4a) is generally carried out 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, butanol, ethyl acetate, acetone, acetonitrile, dimethylsulfoxide, dimethylformamide, hexamethylphosphoric triamide and the like, and mixed solvents thereof. Examples of the basic compound include carbonates such as sodium carbonate, potassium carbonate, sodium hydrogen carbonate and potassium hydrogen carbonate, metal hydroxides such as sodium hydroxide and potassium hydroxide, sodium hydride, potassium, sodium, sodium amide, Metal alcoholates such as sodium methylate and sodium ethylate, pyridine, N-ethyldiisopropylamine, dimethylaminopyridine, triethylamine, DB
Organic bases such as N, DBU, DABCO and the like can be mentioned. The use ratio of the compound of the general formula (1a) and the compound of the general formula (4a) is not particularly limited and may be appropriately selected within a wide range, but the latter is at least about an equimolar amount with respect to the former, preferably It is preferable to use an equimolar to 10-fold molar amount. The reaction is usually carried out at about 0 to 200 ° C., preferably about 0 to 170 ° C., and generally 30 minutes to 3
The reaction is completed in about 0 hours. An alkali metal halogen compound such as sodium iodide or potassium iodide may be added to the reaction system. Further, ammonium halides such as tetra-n-butylammonium iodide, tetra-n-butylammonium bromide, -n-butyltriethylammonium iodide, tetraethylammonium iodide, and tri-n-butylmethylammonium iodide. May be added.

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

When formic acid is used as the reducing agent, the reaction temperature is usually room temperature to 200 ° C., preferably 50 to 150.
A temperature around about 0 ° C is suitable and the reaction is completed in about 1 to 10 hours. Formic acid is preferably used in a large excess amount with respect to compound (1a).

When a hydrogenating / reducing agent is used, the reaction temperature is usually about -30 to 100 ° C, preferably 0 to 70 ° C.
The degree is appropriate, and the reaction is completed in about 30 minutes to 15 hours. The amount of the reducing agent used is usually an equimolar to 20 times molar amount, preferably 1 to 6 times molar amount with respect to the compound (1a). Particularly when lithium aluminum hydride is used as the reducing agent, it is preferable to use ethers such as diethyl ether, dioxane, tetrahydrofuran and diglyme, and aromatic hydrocarbons such as benzene, toluene and xylene as the solvent.

When a catalytic reducing agent is further used, it is usually in a hydrogen atmosphere at atmospheric pressure to 20 atm, preferably atmospheric pressure to 10 atm, or a hydrogen donor such as formic acid, ammonium formate, cyclohexene and hydrazine hydrate. In the presence of, 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 is compound (1
It is usually 0.1 to 40% by weight, preferably 1 to
It is preferable to set it to about 20% by weight.

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

[0657]

[Chemical Formula 39]

[Wherein R ¹ , R ² , R ³ , R ⁴ , r, m and n are the same as defined above]. The reaction for leading the compound (1c) to the compound (1d) and the reaction for leading 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, formic acid, acetic acid, organic acids such as trifluoroacetic acid, alcohols such as methanol and ethanol, halogenated hydrocarbons such as chloroform and dichloromethane, or a mixed solvent thereof. it can. Examples of the oxidizing agent used include 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,
Dichromate such as potassium dichromate, permanganate,
Examples thereof 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 2 times the molar amount of the starting material. The above reaction is usually performed at -10 to 40 ° C, preferably -10 ° C to around room temperature, and is completed in about 1 to 100 hours.

[0659]

[Chemical 40]

[In the formula, R ¹ , R ² , R ^3a , R ⁸ and the groups represented by the above [Chemical Formula 29], r, m, n, X and l are the same as defined 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, or 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, which may have a halogen atom, a lower alkoxy group as a substituent or a lower alkanoyl group as a substituent on the phenyl ring Having 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 as a substituent Amino group with 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 alkenyl carbonyl group, a halogen atom as a substituent on the phenyl ring, a lower alkoxy group, an amino group which may have a lower alkanoyl group as a substituent, and a hydroxyl group. A benzoyl group optionally having 1 to 3 selected groups or an amino group-substituted lower alkanoyl group optionally having a lower alkanoyl group as a substituent is shown. R ^10b is a lower alkyl group, a morpholinocarbonyl lower alkyl group, a lower alkylsulfonyl group, an aminocarbonyl group that may have a lower alkyl group as a substituent, or a phenylsulfonyl group that may have a lower alkyl group as a substituent on the phenyl ring. Group, a phenyl lower alkenyl group, an amino group-substituted sulfonyl group which may have a lower alkyl group as a substituent, or a phenyl lower alkyl group. q'represents 1 or 2. R ^10c and R ^10d
Each represents a hydrogen atom or a lower alkyl group. The reaction between the compound (1g) 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 reaction formula-1.

The compound (1h) in which R ^10a is a lower alkanoyl group can be represented by the general formula (R ¹¹ ) ₂ O (7) or the general formula R ¹¹ X (8) [in the above formulas, R ¹¹ is a lower alkanoyl group]. Indicates a group. X is the same as above. ] It can also be derived by lower alkanoylating the compound (1g) with a compound represented by the formula: This lower alkanoylation reaction is carried out in the presence or absence of a basic compound.
Examples of the basic compound used include alkali metals such as sodium metal and potassium, and hydroxides, carbonates, bicarbonates of these alkali metals, or organic bases such as N, N-dimethylaminopyridine, pyridine and piperidine. Etc. can be mentioned. The reaction proceeds with or without 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 an amount of at least about equimolar to the starting compound, but it is generally preferred to use equimolar to large excess amount thereof.
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 5 minutes to 5 minutes.
It's 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 the reaction of the compound (1a) with the compound (4a) or the compound (4b) in the reaction formula-2. To be done.

[0663]

Embedded image

[Wherein R ¹ , R ² , R ⁸ , R ^3a , m, n,
q ′, R ⁹ , R ¹⁰ , r and the group represented by the above [Chemical Formula 29] are the same as above. R ¹² represents a lower alkyl group. The hydrolysis reaction of compound (1j) can be carried out in a suitable solvent or without solvent, in the presence of an acid or a basic compound. Examples of the solvent used include 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, and the like. These mixed solvent etc. 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, and examples of the basic compound include sodium carbonate and potassium carbonate. Examples thereof include metal acid salts and metal hydroxides such as sodium hydroxide, potassium hydroxide and calcium hydroxide. The reaction normally proceeds suitably at room temperature to 200 ° C, preferably at room temperature to 150 ° C, and is generally completed in about 10 minutes to 25 hours.

The reaction between the compound (1k) and the compound (9) is carried out under the same conditions as in the reaction between the compound (2) and the compound (3) in the reaction formula-1.

[0666]

Embedded image

[Wherein R ¹ , R ² , R ^3a , R ⁸ , m, n,
q ′, X, and the group represented by the above [Chemical Formula 29] are the same as 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. A substituted lower alkyl group, a lower alkenyl group, a lower alkanoyl group or a morpholinocarbonyl lower alkyl group is shown. 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. When the R ¹⁴ is a phenyl lower alkoxy group, the reaction for converting the compound (1o) to the compound (1m) is
It is carried out by reducing m). This reduction reaction can be carried out, 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 mixed solvents thereof. As the catalyst used, for example, palladium, palladium-
Examples include black, palladium-carbon, platinum, platinum oxide, copper chromite, Raney nickel and the like. The amount of catalyst used is
Generally, 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,
The hydrogen pressure is preferably about 0 to 80 ° C. and the hydrogen pressure is usually 1 to 10 atm, and 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 compound (1m) is carried out by hydrolyzing compound (1o). The hydrolysis is carried out in the presence of acid in a suitable solvent. 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 a mixture thereof. A solvent etc. 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 and potassium iodide. And the mixture of the above Lewis acid and iodide. The reaction is usually 0 ~ 150 ℃,
The reaction proceeds preferably at room temperature to 100 ° C., and is generally 0.
It takes about 5 to 50 hours to finish.

When R ¹⁴ is a lower alkanoyloxy group, the reaction for converting the compound (1o) to the compound (1m) can be carried out under the same reaction conditions as in the hydrolysis reaction of the compound (1j) in the above Reaction scheme-5. Get to.

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

[0671]

[Chemical 43]

[Wherein R ¹ , R ² , R ^3a , R ⁵ , R ⁸ and
The groups represented by m, n, q ', A, X, r and the above [Chemical Formula 29] are the same as above. p'represents 1 or 2. The halogenation reaction of compound (1p) or compound (1E) is carried out in the presence of a usual halogenating agent. As the halogenating agent used in such a reaction, a wide variety of known ones can be used. For example, halogen molecules such as bromine and chlorine or iodine monochloride, sulfuryl chloride, N-bromosuccinimide, N-chlorosuccinimide and the like are used. And halogenating agents such as halogenosuccinimide.
The amount of the halogenating agent to be used is usually at least equimolar, preferably equimolar to 1.5 times the molar amount of the compound (1p) or the 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 mixed solvents thereof. In the reaction, the reaction temperature is usually 0 ° C to
The boiling point of the reaction solvent is preferably 0 to 100 ° C., and the reaction is usually completed in about 1 to 10 hours.

[0673]

[Chemical 44]

[Wherein R ¹ , R ² , R ^3a , R ⁸ , m, n,
q ', X, r and the group represented by the above [Chemical Formula 29] are the same as 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 carried out in a suitable solvent in the presence of an oxidizing agent. Examples of the oxidant used here include pyridinium chlorochromate, pyridinium chromate such as pyridinium dichlorochromate, dimethyl sulfoxide-oxalyl chloride, manganese dioxide, DDQ, dichromic acid, sodium dichromate, dichromic acid. Examples thereof include dichromates such as potassium, permanganate, potassium permanganate, permanganates such as sodium permanganate, and the like. Examples of the solvent used include water, formic acid, acetic acid, organic acids such as trifluoroacetic acid, alcohols such as methanol and ethanol,
Examples thereof include halogenated hydrocarbons such as chloroform and dichloromethane, ethers such as tetrahydrofuran, diethyl ether and dioxane, dimethyl sulfoxide, dimethylformamide, and mixed solvents thereof. The oxidizing agent is usually used in an amount of at least equimolar, preferably equimolar to 30 times the molar amount of 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 the compound (1r) to the compound (1s) is carried out by reacting the compound (1r) with an oxidizing agent in the presence of a co-oxidizing agent in a suitable solvent. Examples of the solvent used in the reaction with the oxidizing agent include pyridine, dioxane, tetrahydrofuran, ethers such as diethyl ether, aromatic hydrocarbons such as benzene, toluene, xylene, dichloromethane, dichloroethane, chloroform, carbon tetrachloride and the like. Examples thereof include halogenated hydrocarbons, esters such as ethyl acetate, alcohols such as water, methanol, ethanol, isopropanol and t-butanol, and mixed solvents thereof. Examples of the co-oxidant used include pyridine N-oxide, N
-Organic amine N such as ethyldiisopropylamine N-oxide, N-methylmorpholine N-oxide, trimethylamine N-oxide and triethylamine N-oxide
Examples thereof include oxides. Examples of the oxidizing agent include tetra-n-propylammonium perruthenate. The amount of the co-oxidizing agent used is usually at least an equimolar amount, preferably equimolar to the starting compound.
It is preferable to use a 5-fold molar amount. The oxidizing agent is preferably used in 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 hydrogenation reducing agent is preferably used. Examples of the hydride reducing agent used include lithium aluminum hydride, diborane, diisobutylaluminum hydride, sodium borohydride, lithium borohydride, tetrabutylammonium borohydride, calcium borohydride, and aluminum hydride. ,
The amount used is at least 0.1 times mol, preferably 0.1 to 15 times 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,
Tetrahydrofuran, diethyl ether, diisopropyl ether, diglyme and other ethers, benzene, toluene, xylene and other aromatic hydrocarbons, and mixed solvents thereof, etc. are usually used at about −60 to 150 ° C., preferably −
It is carried out at 30 to 100 ° C. for about 10 minutes to 20 hours.

The reaction of compound (1s) with compound (11) is carried out in a suitable solvent. As the solvent used here, any solvent used in the Grignard reaction can be used, for example, diethyl ether, dioxane, ethers such as tetrahydrofuran, benzene, aromatic hydrocarbons such as toluene, pentane, Preferable examples include saturated hydrocarbons such as hexane, heptane, and cyclohexane. The amount of the compound (11) used is usually at least equimolar, preferably equimolar to 2 times the molar amount of the compound (1s). The above reaction is usually -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) to the compound (1u) is carried out under the same conditions as 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 above Reaction scheme-5.

The reaction between compound (1s) and compound (11a) is carried out in the presence of a basic compound in a suitable solvent. As the basic compound used, inorganic bases such as metallic sodium, metallic potassium, sodium hydride, sodium amide, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate and sodium hydrogen carbonate,
Metallic alcoholates such as sodium methylate, sodium ethylate and potassium t-butoxide, alkyl lithium and lithium amides such as methyl lithium, n-butyl lithium, phenyl lithium and lithium diisopropylamide, lithium amides, pyridine, piperidine, quinoline and triethylamine. , Organic bases such as N, N-dimethylaniline and the like can be exemplified. 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, etc., aromatic hydrocarbons such as benzene, toluene, xylene, n, etc. -Aromatic hydrocarbons such as hexane, heptane and cyclohexane, amines such as pyridine and N, N-dimethylaniline, aprotic polar solvents such as N, N-dimethylformamide, dimethylsulfoxide and hexamethylphosphoric triamide, Examples thereof include alcohols such as methanol, ethanol and isopropanol, or a mixed solvent thereof.
The reaction temperature is generally -80 to 150 ° C, preferably -80.
It is preferable to set the temperature to about 120 ° C, and the reaction is generally completed in about 0.5 to 15 hours. The amount of the compound (11a) used is at least equimolar, preferably equimolar to 10 times the molar amount of the 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 on the phenyl ring as a substituent, a morpholino-substituted lower alkyl group, or 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 group selected from the group consisting of a lower alkyl group and a lower alkoxy group on the phenyl ring as a substituent. The reaction for converting the compound (1x) into the compound (1x ′) is carried out under the same conditions as the reaction for converting the compound (1o) into the compound (1m) in the aforementioned Reaction scheme-6.

The reaction of compound (1x ') with compound (12) is carried out under the same conditions as the reaction of compound (1m) with compound (10) in the aforementioned Reaction scheme-6.

[0684]

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[0685]

[Chemical 47]

[Wherein R ¹ , R ^3a , R ⁸ , m, n, q ',
R ⁵ , p ′, r and the group represented by the above [Chemical Formula 29] are the same as 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 is a group —O—A ₁ —CO—NR ⁶ R ⁷ (A
₁ , R ⁶ and R ⁷ are the same as above. ). ] The reaction for leading the compound (1y) to the compound (1z) and the reaction for leading the compound (1B) to the compound (1C) are the same as those shown in the reaction formula-
It is carried out 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. 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 [Chemical Formula 29] are the same as above. The reaction for leading the compound (1j) to the compound (1G) and the reaction for leading the compound (1H) to the compound (1I) are the same as those in the above reaction formula-
The reaction is conducted under the same conditions as in the reaction for converting compound (1s) to compound (1r) in 8.

[0690]

[Chemical 49]

[Wherein R ¹ , R ² , R ^3a , R ⁵ , A, m,
n, p ′, R ¹² , r and X are the same as 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 the reaction for converting the compound (1s) into the compound (1r) in the aforementioned Reaction scheme-8.

The reaction for converting compound (1K) to compound (1L) is carried out by reacting compound (1K) with a halogenating agent in a suitable solvent or without solvent. Here, as the halogenating agent, a mineral acid such as hydrochloric acid or 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 above-mentioned reaction formula-1
Any of the basic compounds exemplified in the reaction of the carboxylic acid halide and 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, 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 halogenating agent is used in at least an equimolar amount, preferably an equimolar to 2-fold molar amount with respect to the compound (1K). It is good to use a quantity. When other halogenating agent is used, it is preferred to use at least an equimolar amount to the compound (1K), usually in a large excess amount. 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 compound (1L) with compound (13) is carried out under the same conditions as in the reaction of compound (1a) with compound (4a) in the aforementioned Reaction scheme-2.

[0694]

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[Wherein R ¹ , R ² , R ^3a , r, m and n are the same 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 leading the compound (1N) to the compound (1O) and the reaction for leading the compound (1O) to the compound (1P) are the same as those in the above reaction formula-
The reaction is conducted under the same conditions as the reaction for converting compound (1c) to compound (1d) in 3.

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

[0697]

[Chemical 51]

[Wherein R ¹ , R ² , R ^3a , R ⁵ , m, n,
p ′, X, A, A ₁ , r and Y are the same as 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 the phenyl ring, a furyl lower alkyl group or a lower alkoxy-substituted lower alkyl group. Indicates. R ^6b represents the above 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 the same 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 reaction between the compound (1a) and the compound (4a) in the reaction formula-2, respectively. 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 the reaction between the compound (1a) and the compound (4b) in the aforementioned Reaction scheme-2, respectively. To be done. The compound (2) or (3) which is 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 the same as defined above. However, the total number of carbon atoms of the group R ^3b CH ₂ — excluding the cyclic portion of R ^3b in the group R ^3b CH ₂ — of the compound (3a) 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 in a suitable solvent or by hydrolysis. As the solvent used in the reaction with hydrazine, in addition to water, any of the same solvents as those used in the reaction of the compound (2) and the compound (3) in the reaction formula-1 can be used. The reaction is usually at room temperature to about 120 ° C., preferably 0 to
It is carried out at about 100 ° C., and generally completed in about 0.5 to 10 hours. The amount of hydrazine used is at least about equimolar, preferably equimolar to 5 with respect to the compound (17).
It is preferable that the amount is about twice the molar amount.

The above hydrolysis can be carried out in a suitable solvent or without 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, and mixtures thereof. A solvent etc. 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, and 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 normally proceeds suitably at room temperature to 200 ° C, preferably at room temperature to 150 ° C, and is generally completed in about 10 minutes to 25 hours.

[0702]

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[In the formula, 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 (wherein D represents a lower alkylene group, r'represents 0 or 1. R ³³ represents a group

[0704]

[Chemical 54]

(R ⁵ and p are the same as above), lower alkanoyloxy-substituted lower alkyl group, lower alkoxy lower alkyl group, lower alkanoyl group-substituted lower alkyl group, lower alkoxycarbonyloxy-substituted lower alkyl group, on the 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 [Chemical formula 26], a cycloalkyl group, a naphthyl group or a group.

[0706]

[Chemical 55]

(In the formula, R ⁸ and q are the same as defined above.

[0708]

[Chemical 56]

Is a 5- to 14-membered monocyclic, dicyclic or ternary saturated or unsaturated heterocycle having 1 to 4 heteroatoms selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom. Indicates a group. ). ), 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 , 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 above), a lower alkenyloxy group, a nitro group and phenyl which may have a group selected from the group consisting of a lower alkyl group which may have a halogen atom as a substituent. Group, 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 , 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, 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 lower alkenyl group, an phenylthio-substituted lower alkyl group that may have a lower alkoxy group as a substituent on the phenyl ring, and a phenylsulfinyl-substituted lower alkyl group that 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 (in the formula, A ₅ , R ⁴² , R ⁴³ and R ⁴⁴ are the same as above),
2,3-dihydro-1H-, which may have 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 on the 2,3-dihydro-1H-indenyl ring. An indenyl group-substituted lower alkyl group, a group represented by the above [Chemical Formula 34], or a group

[0710]

[Chemical 57]

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

[0712]

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Is a 5- to 14-membered monocyclic, dicyclic or tricyclic saturated or unsaturated heterocyclic group having 1 to 4 heteroatoms selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom. Indicates. ). Provided that R ^3e may have a lower alkoxy group as a substituent, a halogen atom, a lower alkanoyl group or a phenyl lower alkenylcarbonyl group as a substituent on the phenyl ring, and an amino group or a lower alkoxy group substituted 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-N
R 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 group selected from the group consisting of a lower alkyl group which may have a halogen atom as a substituent. Sometimes a phenyl group or the above
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 the reaction between the compound (1a) and the compound (4b) in the above Reaction scheme-2.

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

[0715]

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[Wherein R ^3b , R ¹² and X are the same as defined above]. M
Represents an alkali metal atom such as potassium or 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 carried out under the same conditions as in the halogenation reaction of the compound (1p) in the above Reaction formula-7, but 2- (4-biphenylyl) is present in the reaction system. It is preferable to add a radical initiator such as -5-phenyloxazole or 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 the reaction between the compound (1a) and the compound (4a) in the above Reaction scheme-2.

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

The reaction of the compound (24) with the compound (22b) is carried out in a suitable solvent with diethyl azodicarboxylate,
Dialkylazodicarboxylates such as dibutylazodicarboxylate, azodicarboxylic acid derivatives such as dialkylazodicarboxamides such as 1,1′-azodicarbonyldipiperidine, trialkylphosphines such as trimethylphosphine, triphenylphosphine And the like in the presence of a phosphorus compound such as triarylphosphine. As the solvent used here, any solvent other than the lower alcohols can be used among the solvents used in the reaction of the compound (1a) and the compound (4a) in the above Reaction Formula-2. The amounts of the azodicarboxylic acid derivative, the phosphorus compound and the compound (22b) used are usually at least equimolar, preferably equimolar to 1.5 times the molar amount of the compound (24). The reaction is usually 0 to 100 ° C., preferably 0 to 7
It finishes in about 1 to 15 hours at around 0 ° C.

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

The reaction between compound (26) and compound (22a) is carried out in the presence of formaldehyde and an acid in a suitable solvent. As the solvent used here, for example, dichloromethane, dichloroethane, chloroform, halogenated hydrocarbons such as carbon tetrachloride, water, methanol, ethanol, alcohols such as isopropanol, acetic acid,
Alkanoic acid such as propionic acid, acid anhydride such as acetic anhydride,
Examples include polar solvents such as acetone and dimethylformamide, and mixed solvents thereof. Examples of the acid used include mineral acids such as hydrochloric acid gas, hydrochloric acid and 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) used is usually at least equimolar, preferably equimolar to 2 times the molar amount of the compound (26). Formaldehyde is preferably used in at least an equimolar amount, usually in a large excess amount, with respect to the compound (26). The reaction is usually 0 to 200 ° C., preferably room temperature to 1
The process proceeds appropriately at about 50 ° C. and ends in about 0.5 to 24 hours.

[0722]

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[Wherein R ^3b is the same 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 scheme-8.

[0724]

[Chemical formula 61]

[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 the compound (28) and the compound (29) is carried out under the same conditions as the reaction between the compound (1a) and the compound (4a) in the above Reaction scheme-2.

The reaction for converting the compound (30) to the compound (3d) is carried out by reacting the compound (17) in the reaction formula-15 with the compound (30) when R ³⁴ represents the group represented by the above [Chemical formula 62]. It is carried out under the same conditions as the reaction leading to compound (3a).

When R ^{34 in the} compound (30) represents a group —NR ³⁶ R ³⁷ , it is a reaction for converting the compound (1o) to the compound (1m) in the reaction formula-6, and R ¹⁴ is a phenyl lower alkoxy group. It is carried out under the same conditions as the reduction reaction of a compound.

[0730]

[Chemical formula 63]

[Wherein R ¹ , R ² , R ¹² and r are the same as defined above]. The reaction between compound (31) and compound (32) is carried out in the presence of a basic compound. As the basic compound used here, the compound (1a) in the above Reaction Formula-2 is used.
Any of the basic compounds used in the reaction of the compound with the compound (4a) can be used. The compound (32) is usually used in an amount of at least equimolar, preferably equimolar to 5 times the molar amount of the compound (31). The reaction is usually completed at 0 to 100 ° C., preferably 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 the presence of a phosphorus halide compound such as phosphorus tribromide or phosphorus trichloride in a suitable solvent. Examples of the solvent used include ethers such as dioxane and tetrahydrofuran, halogenated hydrocarbons such as chloroform, methylene chloride and carbon tetrachloride. The phosphorus halide compound is preferably used in an equimolar to 2-fold molar amount with respect to the compound (33a). The reaction is usually 0-100
C., preferably in the vicinity of 0 to 70.degree. C., and completed in about 0.5 to 5 hours.

The reaction for converting the compound (33a) to the compound (33c) is carried out in the presence of an acid in a suitable solvent in the presence of an acid.
It is carried out by reacting a) 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, water and the like. 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 times the molar amount of the compound (33a). The reaction is usually 0 to 100 ° C, preferably 0 to 70 ° C.
It will be completed in about 1 to 10 hours in the vicinity.

The reaction for converting the compound (33c) into the compound (33d) is carried out under the same conditions as the reaction for converting the compound (1c) into the compound (1d) in the above-mentioned Reaction formula-3.

The reaction for converting the compound (33a) into the compound (33d) is the same as the compound (33a) except that a trialkylphosphite such as trimethylphosphite is used as the phosphorus compound instead of the phosphorus halide compound. The reaction is conducted under the same conditions as in the reaction leading to (33b), but alcohols such as 1-propanol may be used as a solvent here, and the reaction temperature is usually 0 to 15
It may be carried out at 0 ° C., preferably around 0 to 100 ° C.

[0736]

[Chemical 64]

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

The esterification reaction of the compound (2) is carried out by reacting the starting compound with methanol in the presence of a mineral acid such as hydrochloric acid or sulfuric acid, a halogenating agent such as thionyl chloride, phosphorus oxychloride, phosphorus pentachloride or phosphorus trichloride. It is carried out by reacting with alcohols such as ethanol and isopropanol usually at 0 to 150 ° C., preferably at 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 scheme-22.

[0740]

Embedded image

[Wherein R ⁸ , q ′ and R ¹² are the same as defined above]. The reaction for converting the compound (20a) to the compound (20b) is carried out 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 leading the compound (1c) to the compound (1d) in the above Reaction Formula-3 can be used. It is usually preferable to use the oxidizing agent in a large excess amount with respect to the compound (20a). The reaction is usually room temperature to 150 ° C., preferably room temperature to 120 ° C.
The process is completed in about 1 to 20 hours at around 0 ° C.

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

The reaction for converting the compound (20c) to the compound (24a) is carried out under the same conditions as in the hydrolysis reaction of the compound (1j) in the aforementioned Reaction scheme-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, a metal or metal salt and an acid, or a metal or metal salt and an alkali metal hydroxide or sulfide. , A mixture with an ammonium salt or the like is used as a reducing agent for reduction.

When the reducing catalyst of [0746] 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 the like, esters such as ethyl acetate and methyl acetate, aprotic polar solvents such as N, N-dimethylformamide and the like, or mixed solvents thereof and the like. Examples of the catalytic reduction catalyst used include palladium, palladium-black, palladium-carbon, platinum, platinum oxide, copper chromite, Raney-nickel and the like. It is generally preferable to use the catalyst 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
It is preferable that the pressure is -10 atm, and the reaction is generally 0.5-1.
It will be finished in about 0 hours. An acid such as hydrochloric acid may be added to the reaction.

When the other method is used, iron, zinc, tin or stannous chloride and a mineral acid such as hydrochloric acid or sulfuric acid, or an alkali metal hydroxide such as iron, ferrous sulfate, zinc or tin and sodium hydroxide is used. A mixture of a substance, a sulfide such as ammonium sulfide, aqueous ammonia, and an ammonium salt such as ammonium chloride is used as the reducing agent. Examples of the inert solvent used include water, acetic acid, methanol, ethanol,
Dioxane etc. can be illustrated. The conditions of 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 agents, it is preferably 0 ° C. to room temperature, about 0.5 to 10 hours. It is better to carry out the reaction. The reducing agent is used in at least an equimolar amount, usually an equimolar to 5-fold molar amount with respect to the starting compound.

[0748]

[Chemical formula 66]

[Wherein R ¹ , R ² , R ^3a , R ⁸ , R ³⁹ ,
The groups represented by m, n, q ', D, r, r'and [Chemical Formula 29] are the same as above. R ⁴⁸ represents a lower alkoxy group.
R ⁴⁹ represents lower alkoxycarbonyl. R ⁵⁰ and R ⁵¹
Are the same or different and represent 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. Examples of the basic compound 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, sodium methylate and sodium ethylate. , Metal alcoholates such as potassium t-butoxide, alkyl and aryl lithium or lithium amides such as methyllithium, n-butyllithium, phenyllithium, lithium diisopropylamide, pyridine, piperidine, quinoline, triethylamine, N, N-dimethylaniline. Examples thereof include organic bases and the like. As the solvent, any one 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, aliphatic hydrocarbons such as n-hexane, heptane and cyclohexane, pyridine,
Examples thereof include amines such as N, N-dimethylaniline, aprotic polar solvents such as N, N-dimethylformamide, dimethylsulfoxide, and hexamethylphosphoric triamide, alcohols such as methanol, ethanol, and isopropanol. The reaction temperature is usually -80 to 150 ° C,
The temperature is preferably about -80 to 120 ° C, and the reaction is generally completed in about 0.5 to 15 hours.

The reaction for converting the compound (1V) to the compound (1W) can be carried out under the same reaction conditions as in the hydrolysis reaction of the compound (1j) in the above Reaction scheme-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 reaction formula-1.

[0752]

Embedded image

[Wherein R ¹ , R ² , m, n, r and R ^3a are the same as defined 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 the same as 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 reaction formula-1. Here, the reaction between the carboxylic acid anhydride and the amine is usually 0 to 150 in the presence of the same solvent and basic compound as in the reaction using the active ester method in the reaction between the compound (2) and the compound (3).
℃, preferably 10 to 100 ℃, generally 5 ~
It will be completed in 30 hours. The amount of the carboxylic acid anhydride used is at least equimolar, preferably equimolar to 2 times the molar amount of the compound (1a).

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

R ⁷ 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 formula (1), the corresponding R ⁵ is a lower alkanoyl group or R ⁸
To a compound in which is a lower alkanoyl-substituted lower alkyl group,

[0756]

[Chemical 68]

It can be obtained by reacting a compound represented by the formula (wherein R ³⁸ represents a lower alkyl group, v represents 0 or an integer of 1 to 3). The reaction is carried out in the presence of acid in a suitable solvent. As the solvent used here, in addition to halogenated hydrocarbons such as methylene chloride, dichloroethane and chloroform, the above reaction formula-
Any of the solvents used in the compound (1a) and the 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,
It is preferable to use an equimolar to 10-fold molar amount. The reaction is usually room temperature to 150 ° C., preferably room temperature to 100 ° C.
It is completed in about 1 to 24 hours at around C.

A general formula (1) in which R ⁵ represents a lower alkanoyl group or R ⁸ represents a lower alkanoyl group-substituted lower alkyl group.
The compound of R is a 1.3-dioxolanyl group or R in which the corresponding R ⁵ may have a lower alkyl group as a substituent.
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 carried out in the presence of an acid in a suitable solvent. Examples of the solvent used here include:
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-tolueresulfonic acid. The reaction is usually 0 to 70 ° C., preferably 0 ° C. to around room temperature,
It will be completed 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) (R in the formula
³⁹ represents a lower alkyl group or a lower alkoxy lower alkyl group. X is the same as above. ) Is reacted under the same conditions as the reaction of the compound (10) with the compound (4a) in the above-mentioned reaction formula-2.

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

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 is a compound in which R ² represents a lower alkyl group having a halogen atom and morpholine or imidazole. It is produced by reacting the compound (1a) and the compound (4a) in the reaction formula-2 under the same conditions.

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

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

Of the compounds of the present invention represented by the general formula (1), the compound having an acidic group can be easily converted into a salt by reacting 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 thus obtained in each step can be easily isolated and purified by a conventional separation means. Examples of the separating means include a solvent extraction method,
Examples include dilution method, recrystallization method, column chromatography, preparative thin layer chromatography and the like.

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

The compound of general formula (1) is usually used in the form of general pharmaceutical preparations. The preparation is prepared by using a diluent or an excipient such as a filler, a filler, a binder, a moisturizer, a disintegrant, a surface active agent and a lubricant which are usually used. Various forms of this pharmaceutical preparation can be selected according to the therapeutic purpose, and typical examples thereof include tablets, pills, powders, solutions, suspensions, emulsions, granules, capsules, suppositories, and injections ( Liquid preparations, suspensions, etc.) and the like. In the case of molding in the form of tablets, those conventionally known in this field can be widely used as carriers, for example, lactose, sucrose, sodium chloride,
Excipients such as glucose, urea, starch, calcium carbonate, kaolin, crystalline cellulose, silicic acid, water, ethanol, propanol, simple syrup, glucose solution, starch solution, gelatin solution, carboxymethylcellulose, shellac, methylcellulose, potassium phosphate , Binders such as polyvinylpyrrolidone, dry starch, sodium alginate, agar powder, laminaran powder, sodium hydrogen carbonate, calcium carbonate, polyoxyethylene sorbitan fatty acid esters, sodium lauryl sulfate, stearic acid monoglyceride, starch, disintegrants such as 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 tablet may be a tablet coated with a usual coating, if necessary, such as a sugar-coated tablet, a gelatin-coated tablet, an enteric-coated tablet, a film-coated tablet, a double tablet, or a multi-layer tablet. In the case of molding in the form of pills, those conventionally known in this field 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 thereof include tragacanth powder, a binder such as gelatin and ethanol, and a disintegrating agent such as laminaranthantene. In the case of molding 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 semisynthetic glycerides. When prepared as an injection, it is preferable that the solution and suspension are sterilized and isotonic with blood. 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 sodium chloride, glucose or glycerin to prepare an isotonic solution may be contained in the pharmaceutical preparation, and a usual solubilizing agent, buffer, soothing agent, etc. may be added. May be. If necessary, colorants, preservatives, fragrances,
Flavors, sweeteners, 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.
It is preferable to set it to 0% by weight.

The administration method of the above-mentioned pharmaceutical preparation is not particularly limited, and it is administered according to various preparation forms, patient's age, sex and other conditions, degree of disease and the like. For example, tablets, pills, solutions, suspensions, emulsions, granules and capsules are orally administered. Further, in the case of an injection, it is administered alone or mixed with an ordinary replenisher such as glucose and amino acid, and then intravenously administered, and if necessary, it is intramuscularly, intradermally, subcutaneously or intraperitoneally administered. Suppositories are administered rectally.

The dose of the above-mentioned pharmaceutical preparation is appropriately selected depending on the usage, age of the patient, sex and other conditions, degree of disease and the like, but usually the amount of the compound of the general formula (1) or a salt thereof which is an active ingredient. Is about 0.2 to 200 per 1 kg of body weight per day
It is good to set it to about mg.

Formulation Example 1 2- (2-Benzofuranylmethylaminocarbonyl) -3-methyl quinoxaline-4-oxide 5 mg Starch 132 mg Magnesium stearate 18 mg Lactose 45 mg Total 200 mg Tablets of the above composition in 1 tablet according to a conventional method. 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 Propyl methyl cellulose 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 a sugar coated R10 mm kine. The obtained tablets are coated with a film coating agent consisting of hydroxypropylmethyl cellulose, polyethylene glycol-6000, castor oil and methanol to produce film coated tablets.

Reference Example 1 2-Ethoxycarbonyl-3-methylbenzofuran 5.
10 ml of 0 g of anhydrous diethyl ether solution was added with 0.93 g of lithium aluminum hydride and 30 m of diethyl ether.
1 was added dropwise to the suspension solution under ice cooling. After stirring at room temperature for 30 minutes,
Cooled, decomposed with saturated aqueous sodium sulfate solution, filtered through Celite, and dried 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 = 6Hz), 2.27 (3H,
S), 4.76 (2H, d, J = 6Hz), 7.20-
7.55 (4H, m).

Reference Example 2 2-Hydroxymethyl-3-methylbenzofuran 3.7
g, 6.6 g of triphenylphosphine and 3.7 g of phthalimide were suspended in 40 ml of tetrahydrofuran, a solution of 4.4 g of diethyl azodicarboxylate in 10 ml of tetrahydrofuran was added dropwise under ice cooling, and the mixture was stirred overnight at room temperature. The solvent was evaporated, the residue was purified by silica gel chromatography (elution solvent; methylene chloride), diethyl ether was added for crystallization, and the crystals were collected by filtration and dried to give 4.6 as a white powder.
g of 3-methyl-2-phthalimidomethylbenzofuran was 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 =
7Hz) 7.48 (1H, d, J = 7Hz), 7.65
-7.75 (2H, m), 7.80-7.90 (2H,
m).

Reference Example 3 3-Methyl-2-phthalimidomethylbenzofuran 4.
6 g was added to 80 ml of methanol, 1.2 g of hydrazine hydrate was added, and the mixture was allowed to flow for 3 hours. The solvent was distilled off, diluted aqueous sodium hydroxide solution was added to the residue, and the mixture was extracted 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 insoluble material was 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, 5.0 g of potassium phthalimide was added, and the mixture was stirred at 60 ° C. for 2 hours. Dimethylformamide was distilled off, the residue was extracted with chloroform, washed with water and saturated saline, and then 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.

¹ H-NMR (CDCl ₃ ) δ ppm;
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.
dissolved in 1, and cooled with ice, sodium borohydride 1.1 g
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 = 5Hz), 4.85 (2H,
d, J = 5 Hz), 7.20-7.45 (2H, m),
7.53 (1H, d, J = 8Hz), 7.62 (1H,
s), 7.68 (1H, d, J = 8Hz).

Reference Example 7 An anhydrous toluene solution of 3.46 g of ethyl 2-benzofuran acrylate was cooled to -50 ° C, and diisobutylaluminum hydride (1M toluene solution, 37 ml) was added dropwise. After stirring at -20 ° C for 1 hour, 30 ml of methanol
Was added, and the mixture was 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 2- (3-hydroxy-1-propenyl) benzofuran as a colorless liquid.

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, the obtained residue and 18.5 g of potassium phthalimide were dissolved in 100 ml of dimethylformamide, and the mixture was stirred at 60 ° C. for 1.5 minutes.
Heated for hours. After cooling, it was poured into ice water and the precipitated crystals were collected by filtration. The obtained crystals were washed with diisopropyl ether to give pale brown crystals of 3-phthalimidomethylbenzothiophene 1
3.4 g was 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 = 8Hz).

Reference Example 9 3.2 g of 2-acetylbenzofuran was added to 60 m of methanol.
It was dissolved in 1 and 15 g of ammonium acetate and 1.26 g of sodium cyanoborohydride were added. After stirring overnight at room temperature, dilute hydrochloric acid ice solution was added to acidify the mixture, 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 the chloroform layer was washed 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 = 6Hz), 1.83 (2H,
brs), 4.20 (1H, q, J = 6Hz), 6.5
0 (1H, s), 7.15-7.30 (2H, m),
7.43 (1H, d, J = 8Hz), 7.51 (1H,
d, J = 8 Hz).

Reference Example 10 25 g of 5-ethyl-2-methylpyridine was added to 200 m of acetic acid.
Dissolve in 1 and add 25 ml of 30% hydrogen peroxide solution,
Heated to 100 ° C. After 4 hours, 25 ml of a 30% hydrogen peroxide aqueous 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 the mixture, and the resulting residue was neutralized with 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 sodium hydrogen carbonate solution was added, and the mixture was extracted with 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 the mixture was stirred at room temperature for 12 hours. After the solvent was distilled off, water was added, the mixture was extracted with chloroform and dried over anhydrous potassium carbonate. After distilling off the solvent, the obtained residue was subjected to silica gel column chromatography (eluting solvent; ethyl acetate: n-).
Hexane = 1: 4) and light brown liquid 5-ethyl-
20.4 g of 2-hydroxymethylpyridine was obtained.

¹ H-NMR (CDCl ₃ ) δ ppm;
1.26 (3H, t, J = 8Hz), 2.66 (2H,
q, J = 8 Hz), 3.67 (1H, br), 4.73
(2H, s), 7.18 (1H, d, J = 8Hz),
7.52 (1H, d, J = 8Hz), 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 reacting for 14 hours at room temperature, the reaction solution was mixed with 1 ml of water and 3 ml of 8 molar aqueous sodium hydroxide solution.
Was added. Further magnesium sulfate was added, and the insoluble material was filtered off. The solvent was concentrated to give a colorless oil [4- (2-methyl-
2.1 g of 1.3-dioxolan-2-yl) benzyl] amine were obtained.

¹ H-NMR (CDCl ₃ ) δ ppm;
7.45 (2H, d, J = 8Hz), 7.29 (2H,
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.
10 g of potassium carbonate was added, and the mixture was stirred at 70 ° C. overnight. Dimethylformamide was distilled off, the residue was extracted with diethyl ether, washed with water, and then dried over anhydrous sodium sulfate. Diethyl ether was distilled off, and the crystals were crystallized from n-hexane, collected by filtration and dried to give 13.9 g of N- as white powder.
[2- (4-Methoxyphenylthio) ethyl] phthalimide was obtained.

¹ H-NMR (CDCl ₃ ) δ ppm;
3.14 (2H, t, J = 7Hz), 3.75 (3H,
s), 3.89 (2H, t, J = 7Hz), 6.80.
(2H, d, J = 8 Hz), 7.42 (2H, d, J =
8 Hz), 7.65-7.75 (2H, m), 7.75
~ 7.90 (2H, m).

Reference Example 13 N- (2-chloroethyl) dibenzylamine.hydrochloride 2
Dimethylformamide 1 was added to 5 g and 8.0 g of phenol.
It was dissolved in 00 ml, 30 g of potassium carbonate 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 oily substance.

¹ H-NMR (CDCl ₃ ) δ ppm;
2.90 (2H, t, J = 6Hz), 3.72 (4H,
s), 4.03 (2H, t, J = 6Hz), 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 filtered off and ethanol was distilled off to obtain 11.0 g of 2-phenoxyethylamine as a colorless oily substance.

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 benzofuroxan and ethyl acetoacetate 207
g was added to 1.5 liters of triethylamine, and the mixture was stirred for 4 days at room temperature. The precipitated crystals were collected by filtration, washed with water, dried and then 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 dripped. 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 recrystallized from n-pentane to give colorless needle crystals 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 was dissolved in 700 ml of methylene chloride, and 70 g of metachloroperbenzoic acid was gradually added under ice cooling. After stirring overnight at room temperature, the reaction solution was washed with a dilute aqueous solution of sodium thiosulfate, saturated aqueous sodium hydrogen carbonate and water in this order, and dried over anhydrous sodium sulfate. The solvent was evaporated, n-hexane was added to the residue, the crystals were collected by filtration, dried and recrystallized from n-hexane-diethyl ether to give colorless needle crystals of 2-ethoxycarbonyl-3-methylquinoxaline-4-oxide. 45 g were obtained. m. p. 91-9
3 ° C.

Reference Example 18 2-Ethoxycarbonyl-3-methylquinoxaline-
Chloroform 500 ml with 1.4-dioxide 105 g
Was dissolved in, 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, 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),
Recrystallization from ethyl acetate-n-hexane gave 35 g of 2-ethoxycarbonyl-3-methylquinoxaline-1-oxide as colorless prism crystals. 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 stirred at room temperature for 3 hours. Methanol was distilled off, water was added to the residue to dissolve it, and the aqueous layer was washed with ethyl acetate. Precipitated crystals were collected by filtration, washed with water and dried by acidification with hydrochloric acid to obtain 3.2 g of 2- as 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 20 g of methanol.
After dissolving in ml, 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, the obtained 2-methoxycarbonylquinoxaline was dissolved in 40 ml of methylene chloride,
2.9 g of metachloroperbenzoic acid was added with stirring at room temperature, and the mixture was stirred overnight at room temperature. The reaction mixture was washed with diluted aqueous sodium thiosulfate solution and saturated aqueous sodium hydrogen carbonate, and dried over anhydrous sodium sulfate. The solvent was distilled off, and n-hexane was added to the residue for crystallization, which was collected by filtration and dried 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.
2 g was dissolved in 40 ml of carbon tetrachloride, 2.7 g of N-bromosuccinimide and 0.2 g of perbenzoic acid were added, and the mixture was heated under reflux for 8 hours. After the solvent was distilled off, 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 the solvent was distilled off, water was added, the mixture was extracted with chloroform and dried over anhydrous sodium sulfate. After distilling off the solvent, the obtained residue was subjected to silica gel column chromatography (eluting solvent;
Dichloromethane: methanol = 16: 1) to obtain 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 = 7Hz), 4.55 (2H,
q, J = 7 Hz), 5.82 (2H, s), 7.04
(2H, d, J = 5Hz), 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 Reference Example 3,
Similar to Nos. 9, 11 and 14, Nos. Shown in Tables 1 to 16 below. 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 suitable starting materials, the above Reference Examples 15 to
Similar to No. 21, Nos. Shown in Tables 17 to 21 below. 1 to
No. 18 compounds were obtained.

[0827]

[Table 17]

[0828]

[Table 18]

[0829]

[Table 19]

[0830]

[Table 20]

[0831]

[Table 21]

Using suitable starting materials, the above Reference Example 3,
Similar to Nos. 9, 11 and 14, Nos. Shown in Tables 22 to 63 below. 1 to No. 126 compounds were obtained.

[0833]

[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]

[0872]

[Table 61]

[0873]

[Table 62]

[0874]

[Table 63]

Using appropriate starting materials, the above Reference Examples 15 to
No. 21 shown in Tables 64 to 65 below as in No. 21. 1 to
No. 7 compound was obtained.

[0876]

[Table 64]

[0877]

[Table 65]

Using suitable starting materials, the above Reference Example 3,
In the same manner as in 9, 11, and 14, the following compounds No. 1 to 26 were obtained.

[0879]

[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 suitable starting materials, the above Reference Examples 15 to
In the same manner as in No. 21, the following compounds No. 1 to 6 were obtained.

[0889]

[Table 75]

[0890]

[Table 76]

Example 1 Under an atmosphere of nitrogen, 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 (elution solvent; n-hexane: ethyl acetate = 3: 1) and recrystallized from ethanol to obtain 1.3 g of 2 as colorless needle crystals.
-[(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.
The resulting solution was dissolved in, and 0.8 g of diethyl cyanophosphate and then 0.8 g of triethylamine were sequentially added dropwise under ice cooling. The mixture was stirred overnight at room temperature, extracted with ethyl acetate, washed with water, and dried over anhydrous sodium sulfate. The solvent was evaporated, the residue was purified by silica gel chromatography (elution solvent; n-hexane: ethyl acetate = 1: 1), and recrystallized from acetonitrile to give 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, 0.7 g of dicyclohexylcarbodiimide was added, and after stirring for 30 minutes, 0.5 g of 2-aminomethylbenzofuran was added and stirred overnight. The insoluble material was filtered off, the organic layer was washed with saturated aqueous sodium hydrogen carbonate and water, and dried over anhydrous sodium sulfate. The solvent was evaporated, the residue was purified by silica gel chromatography (elution solvent; n-hexane: ethyl acetate = 3: 1), and recrystallized from n-hexane-ethyl acetate to give 0.43 g of colorless flake 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, saturated aqueous sodium hydrogen carbonate and water in that order, and dried over anhydrous sodium sulfate.
The solvent was evaporated, the residue was purified by silica gel chromatography (elution solvent; ethyl acetate), and recrystallized from acetonitrile to give 1.5 g of 2-[(4-
Morpholinocarbonylmethoxybenzyl) aminocarbonyl] -3-methylquinoxaline-4-oxide was obtained. m. p. 142-143 ° C.

The following Examples 28 to 103, 125, 126 and 12 were carried out in the same manner as in Example 4 using appropriate starting materials.
8, 130-135, 137, 138, 141, 143
~ 146, 148, 150, 152, 154 to 157,
159, 161, 163, 165, 167, 169, 1
71, 173, 175, 177 to 184, 187 to 18
9, 191, 192, 194, 196 to 201, 203
~ 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.
The 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. It was poured into ice water, extracted with diethyl ether, washed with water, and dried over anhydrous sodium sulfate. The solvent was evaporated, 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.

¹ H-NMR (CDCl ₃ ) δ ppm;
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 = 16Hz), 7.20-7.
50 (5H, m), 7.70-7.85 (2H, m),
8.00-8.15 (2H, m).

The following Examples 44, 66, 107, 110, 135 were prepared in the same manner as in Example 5 using appropriate starting materials.
138, 150, 151, 152, 153, 175, 1
The compounds of 76, 178, 186, 187, 191 and 192 were obtained.

Example 6 0.4 g of 2-[(5-aminobenzofuran-2-yl) methylaminocarbonyl] -3-methylquinoxaline-4-oxide was suspended in 6 ml of pyridine, and acetic anhydride of 0.1. 26 g was added dropwise. After stirring at room temperature for 1 day, the mixture was poured into ice water, and the precipitated crystals were collected by filtration and washed with water. The crude crystal was recrystallized from acetonitrile to give 0.4 g of a pale yellow needle crystal.
-[(5-Acetylaminobenzofuran-2-yl) methylaminocarbonyl] -3-methylquinoxaline-4
-Oxide was obtained. m. p. 183-184 ° C.

The compounds of Examples 84 and 85 below 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, 0.5 g of potassium carbonate and N were added. -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 was distilled off, and the residue was subjected to silica gel chromatography (elution solvent;
Ethyl acetate) and recrystallized as oxalate from ethanol to give 2-[(5-morpholinocarbonylmethylaminobenzofuran-2-yl) methylaminocarbonyl] -3-methylquinoxaline-4 as light brown granular crystals. −
40 mg of oxide was obtained. m. p. 159-167 ° C
(Disassembly).

¹ H-NMR (CDCl ₃ ) δ ppm;
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 = 7Hz),
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 50 ml of methanol and 14 ml of water to obtain 1.4 g of sodium hydroxide. Was added to the dissolved solution and stirred overnight at room temperature. Methanol was distilled off, water was added to the residue to make it acidic, and the precipitated crystals were collected by filtration, washed with water and dried to give 2-[(5-carboxybenzofuran-2-yl) methylaminocarbonyl] -3- as white powder. 3.8 g of methylquinoxaline-4-oxide was obtained. m.
p. 251-252 ° C (decomposition).

Example 9 2.1 g of 2-[(6-methoxymethoxy-3-methylbenzofuran-2-yl) methylaminocarbonyl] -3-methylquinoxaline-4-oxide was dissolved in 20 ml of tetrahydrofuran and 20 ml of methanol, 10 ml of 6N hydrochloric acid was added, and the mixture was refluxed for 1 hour. The solvent was evaporated, the residue was extracted with chloroform, washed with saturated aqueous sodium hydrogen carbonate, water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, the residue was recrystallized from dimethylformamide-water,
1.6 g of 2-[(6-hydroxy-
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 hr. Water was added, and the precipitated crystals were collected by filtration and washed with water. The crude crystals were converted to 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 prismatic crystals. . 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 evaporated, 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 needle crystals.
-Yl) methylaminocarbonyl] -3-methylquinoxaline-4-oxide was obtained. m. p. 170-171
° C.

Using the appropriate starting materials and in the same manner as in Example 11, the following Examples 31, 34, 38, 88, 93, 9 were performed.
The compounds of 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 sodium hydrogen carbonate was added to neutralize it. 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 needle crystals. 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)
, Potassium carbonate (1.8 g) was added, and the mixture was stirred overnight at room temperature. The solvent was distilled off, water was added to the residue, 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 chloroform 30 m
1 g of manganese dioxide was added thereto, and the mixture was refluxed for 6 hours. The reaction solution was filtered through Celite and then concentrated. The residue was recrystallized from ethyl acetate-n-hexane to give 0.5 g of 2-[(5-acetylbenzofuran-2-
Il) methylaminocarbonyl] -3-methylquinoxaline-4-oxide was obtained. m. p. 205-206
° C.

Example 15 2-[(5-Acetylbenzofuran-2-yl) methylaminocarbonyl] -3-methylquinoxaline-4-oxide (0.7 g) was dissolved in anhydrous tetrahydrofuran (20 ml) and methylmagnesium bromide under ice cooling. 2.5 ml of a diethyl ether solution (1M solution) of was added dropwise. The mixture was stirred at room temperature for 3 hours, 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), the crystals were recrystallized from n-hexane-ethyl acetate to give 0.1 g of 2-yellow prism-like crystals.
{[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-
Iyl] methylaminocarbonyl} -3-methylquinoxaline-4-oxide (1.4 g) was added to dimethylformamide 1
It was dissolved in 5 ml, 0.97 g of potassium carbonate and 0.44 g of methyl iodide 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 give 0.48 g of 2-{[5- (2-methyl-5-tetrazolyl) benzofuran-2- as white powder. Yield] methylaminocarbonyl} -3-methylquinoxaline-4-oxide was obtained. m. p. 20
6-209 ° C.

The compounds of Examples 36 and 161 to 164 below were obtained in the same manner as in Example 16 using appropriate starting materials.

Example 17 2-[(4-Methoxycarbonylmethoxybenzyl) aminocarbonyl] -3-methylquinoxaline 3.65 g
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, 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 =
6 Hz), 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 = 6Hz).

Using the appropriate starting materials, the following Example 49 was obtained in the same manner as in Example 17.

Example 18 1.05 g of 2-[(4-carboxymethoxybenzyl) aminocarbonyl] -3-methylquinoxaline was dissolved in 10 ml of dimethylformamide, 0.35 g of furfurylamine was added, and diethyl cyanophosphate was added under cooling with ice. .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 give 0.9 as white powder.
2 g of 2-[(4-furfurylaminocarbonylmethoxybenzyl) aminocarbonyl] -3-methylquinoxaline was obtained. m. p. 175-176 ° C.

Example 19 0.73 g of 2-[(4-methoxycarbonylmethoxybenzyl) aminocarbonyl] -3-methylquinoxaline
And 1.1 ml of 2-methoxyethylamine in 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 was obtained. m. p. 138-140 ° C.

The following Examples 46, 47, 66, 8 were carried out in the same manner as in Examples 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 are 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 mixture was washed with saturated aqueous sodium hydrogen carbonate 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 give 0.6 g of 2- (2-acyl) needle-like 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, 58 were carried out in the same manner as in Examples 10 or 20.
~ 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, 185-193, 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 thereto while stirring with ice cooling. It was After stirring for 3 hours at the same temperature, 0.3m of 10% aqueous sodium hydroxide solution
1 and 0.3 ml of water were sequentially added for decomposition, 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.

¹ H-NMR (CDCl ₃ ) δ ppm;
1.75 (1H, t, J = 6Hz), 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 under ice cooling.
-Methylquinoxaline 9.5 g of tetrahydrofuran 5
The 0 ml solution was slowly added dropwise. 3 times at the same temperature after dropping
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 saturated ammonium chloride aqueous solution was added. The insoluble material was filtered off, extracted with ethyl acetate, and dried over anhydrous sodium sulfate. After the solvent was distilled off, the residue was subjected to silica gel column chromatography (elution solvent; ethyl acetate: n-hexane = 1: 4) to give a yellow liquid 2-{[4- (2-hydroxyethoxy) benzyl] aminocarbonyl}. 1.0 g of 3-methylquinoxaline was obtained.

¹ H-NMR (CDCl ₃ ) δ ppm;
2.25 (1H, br), 3.17 (3H, s), 3.25.
9-4.1 (4H, m), 4.63 (2H, d, J = 6)
Hz), 6.92 (2H, d, J = 7Hz), 7.34
(2H, d, J = 7Hz), 7.7-7.9 (2H,
m), 8.0-8.1 (2H, m), 8.34 (1H,
br).

Example 23 0.2 g of 2-{[4- (2-hydroxyethoxy) benzyl] aminocarbonyl} -3-methylquinoxaline and 0.17 g of triphenylphosphine were mixed with 10 parts of carbon tetrachloride.
It was dissolved in ml and heated under reflux for 1.5 hours. After the reaction,
The solvent was distilled off, and the residue was subjected to silica gel column chromatography (elution solvent; ethyl acetate: n-hexane = 1: 2).
Then, 0.10 g of 2-{[4- (2-chloroethoxy) benzyl] aminocarbonyl} -3-methylquinoxaline as a yellow liquid was obtained.

¹ H-NMR (CDCl ₃ ) δ ppm;
3.17 (3H, s), 3.82 (2H, t, J = 6H
z), 4.24 (2H, t, J = 6Hz), 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, then 1.2 g of sodium iodide and potassium carbonate. 300 mg was added and heated at 60 ° C. for 7.5 hours. After completion of the reaction, the 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) and a yellow liquid was obtained. Then, it was dissolved in ethanol and an ethanol-hydrochloric acid solution was added to dry it. 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).

Using the appropriate starting materials and in the same manner as in Example 24, the compound of the following Example 203 was obtained.

Example 25 2-{[4- (2-methyl-1,3-dioxolane-2
-Yl) benzyl] aminocarbonyl} -3-methylquinoxaline-4-oxide (1.3 g) in acetone (20 ml)
And dissolved in 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 evaporated, the residue was extracted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate, and dried over anhydrous sodium sulfate. The solvent was evaporated,
The residue was recrystallized from ethanol to obtain 1.0 g of 2-[(4-acetylbenzyl) aminocarbonyl] -3-methylquinoxaline-4-oxide as pale yellow needle crystals. 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-was cooled 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 mixture was washed with aqueous sodium thiosulfate solution, saturated aqueous sodium hydrogen carbonate and water, 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 ethanol to give 1.8 g of 2- [2- (4
-Methoxyphenylsulfinyl) ethylaminocarbonyl] -3-methylquinoxaline-4-oxide was obtained. m. p. 156-157 ° C.

[0932] The compounds of Examples 212 and 217 to 220 below 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- was added under ice cooling.
2.8 g of chloroperbenzoic acid was gradually added, and the mixture was reacted at the same temperature for 1 hour. The reaction mixture was washed with aqueous sodium thiosulfate solution, saturated aqueous sodium hydrogen carbonate 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 needle crystals. It was m. p. 14
8 to 150 ° C.

The compounds of Examples 218 and 220 below were obtained in the same manner as in Example 27 using appropriate starting materials.

Using the appropriate starting materials, the above Examples 1, 2
Alternatively, the compounds described in Tables 77 to 135 below were obtained in the same manner as in 3.

[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]

[0966]

[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]

[0977]

[Table 120]

[0980]

[Table 121]

[0981]

[Table 122]

[982]

[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]

Using suitable starting materials, the above Examples 1-4
In the same manner as described above, the compounds shown in Tables 136 to 230 below were obtained.

[0996]

[Table 136]

[0997]

[Table 137]

[0995]

[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]

[1097] Using the appropriate starting materials, the above Examples 1 and 2 were used.
The compounds shown in the following Tables 237 to 259 were obtained in the same manner as in Examples 3 and 4.

[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)
0.6 g of 2-propenyl] aminocarbonyl} -3-methylquinoxaline-4-oxide was added to methylene chloride 40
dissolved in ml, 4-dimethylaminopyridine 0.5 g,
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 diluted hydrochloric acid 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 (eluent: n
-Hexane: ethyl acetate = 3: 1) and then 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.

[1125] Using the appropriate starting materials, the above Examples 443, 444 and 451-453 were conducted 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 an argon stream, and the mixture was stirred at room temperature for 40 minutes. below freezing,
Ethyl chloroformate (440 mg) 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 evaporated, the obtained residue was purified by silica gel column chromatography (eluent: methylene chloride: methanol = 400: 1), and recrystallized with 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 granular.

[1128] 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 was added under ice cooling.
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 at room temperature overnight. The reaction mixture was poured into ice water, extracted with ethyl acetate, washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated and the obtained residue 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- {N. -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 powdery 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 = 7Hz), 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).

[1131] The above-mentioned Examples 443, 444, 451-455 were prepared in the same manner as in Example 482 using appropriate starting materials.
The compounds of 457 and 479 were obtained.

Example 483 Sodium hydride 92 mg dimethylformamide 20
2-{[3-methyl-3- (benzofuran-2-yl) -2-propenyl] aminocarbonyl}-in a ml suspension.
3-methylquinoxaline-4-oxide (746 mg) 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. It was washed with water and saturated saline and then dried. After evaporating the solvent, the obtained residue was purified by silica gel column chromatography, and then diethyl ether-n
Recrystallized from hexane to give 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 needle crystals ¹ H-NMR (CDCl ₃ ) δ ppm; 1.14, 1.
29 (9H, s), 1.66, 2.20 (3H, br
s), 2.62, 2.66 (3H, s), 4.28,
4.59 (2H, d, J = 7.2Hz), 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).

[1134] The above Examples 443, 451-457 and 479 are carried out in the same manner as in Example 483 using appropriate starting materials.
Was obtained.

[1135] Using the appropriate starting materials, the above Examples 1-4
The compounds shown in Tables 262 to 264 below were obtained in the same manner as in.

[1136]

[Table 262]

[1137]

[Table 263]

[1138]

[Table 264]

[1139] Pharmacological test method Glucose uptake test with L6 cells L6 cells (derived from rat striated muscle) were MEM / 10% FCS.
Pre-incubate with (fetal calf serum) and then 4x into a 48-well plate
10 ⁴ cells are seeded and cultured under 2% FCS to differentiate into muscle cells. The test compound was added on the 6th 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]

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Masahito Miyake No. 1 Kamiyashiki, Kitamura, Kitashima-cho, Itano-gun, Tokushima Prefecture Masters L Kitajima Building No. 17, Building No. 102 (72) Inventor Kiyohiko Kumata Nakashiki, Matsushige-machi, Itano-gun, Tokushima Prefecture Nakase Nishinokoshi 39 Address 8 (72) Inventor Hidehiro Yoshida 304-4 Hashimoto Hachimoto, Tokushima City, Tokushima Prefecture (4) 72 Inventor Atsunori Ueyama 4-46 Kitasako Ichibancho, Tokushima City, Tokushima Prefecture Grandor Kita Sako No. 403 (72) Inventor Takao Nishi 28, No. 2 outside of Taro Yasuji, Kitajima-cho, Itano-gun, Tokushima Prefecture

Claims (2)

[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
Indicates. 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-R ⁵² R ⁵³ (R ⁵²
And R ⁵³ are the same or different and each 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 together with the nitrogen atom to which they are bonded via another nitrogen atom or an oxygen atom to form a 5- or 6-membered saturated heterocycle. E represents a lower alkylene group, a group -C (= O)-or a group -C (= O) -A- (A is a lower alkylene group). ); M) group (In the formula, A is the same as above. R ⁵⁴ represents a hydrogen atom or a lower alkyl group.); N) group (In the formula, A represents a lower alkylene group. P represents an integer of 1 to 3. R ⁵ represents a lower alkoxy-substituted lower alkoxy group,
Lower alkoxy group, an amino group which may have a lower alkyl group as a substituent, 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, Lower alkoxycarbonyl substituted lower alkoxy group, lower alkoxycarbonyl group, halogen atom substituted lower alkoxy group, hydroxyl group substituted lower alkoxy group, having a group selected from the group consisting of lower alkyl group and lower alkoxy group as a substituent on the 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 each 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 the phenyl ring, and a furyl-substituted lower alkyl group. Group or a lower alkoxy-substituted lower alkyl group. Also R
⁶ and R ⁷ together with the nitrogen atom to which they are bonded may form a 5- or 6-membered saturated heterocycle with or without a nitrogen atom or an oxygen atom. 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 group-substituted lower group which may have a lower alkoxy group as a substituent, a halogen atom, a lower alkanoyl group or a phenyl lower alkenylcarbonyl group as a substituent on the phenyl ring. 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 and R ⁴¹ are the same or different and each represents a hydrogen atom or a lower alkyl group. R ⁴⁰ and R ⁴¹ represent a nitrogen atom to which they are bonded, another nitrogen atom or oxygen. May be bonded to each other via an atom or not to form a 5- or 6-membered saturated heterocycle), 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. Phenylthio-substituted lower alkyl groups which may have; t) 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)
Phenoxy-substituted lower alkyl group; w) group (In the formula, q represents an integer of 1 to 3. embedded image Is a 5- to 14-membered monocyclic, dicyclic or ternary saturated or unsaturated heterocyclic-substituted lower alkyl having 1 to 4 heteroatoms selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom. Indicates a group. R ⁸ is substituted on the above heterocycle, and R ⁸ is
Having a hydrogen atom, an oxo group, a lower alkyl group that may have a hydroxyl group as a substituent, a halogen atom, a nitro group, a lower alkoxy group, a cyano group, a lower alkoxycarbonyl group, or a lower alkanoyl group as a substituent on the 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 the phenyl ring As a lower alkyl group, a lower alkoxy-substituted lower alkoxy group, a hydroxyl group, a halogen atom and a phenyl group which may have a group selected from the group consisting of a lower alkoxy group, a lower alkenyl group, a morpholinocarbonyl lower alkoxy group,
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,
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,
Aminocarbonyl-substituted lower alkyl group that may have a lower alkyl group as a substituent, lower alkoxycarbonyl group-substituted lower alkenyl group, aminocarbonyl-substituted lower alkenyl group that may have a lower alkyl group as a substituent, and carboxy group-substituted lower alkenyl Group, benzoyl group, lower alkoxy lower alkyl group, group (In the formula, s represents an integer of 1 to 3. embedded image Represents a 5- or 6-membered saturated or unsaturated heterocyclic group having 1 to 4 heteroatoms selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom. R ⁴⁵ is substituted on the above heterocycle,
⁴⁵ represents a hydrogen atom, a lower alkyl group, a lower alkoxy lower alkyl group, a phenyl group or an oxo group. ), The group (In the formula, t represents an integer of 1 to 3. embedded image Represents a saturated or unsaturated heterocyclic-substituted lower alkyl group of 5 to 6 membered ring having 1 to 4 heteroatoms selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom. R ⁴⁶ is substituted on the heterocyclic ring, R ⁴⁶ represents a hydrogen atom, a lower alkyl group or an oxo group. ), Or a group — (C═O) lNR ⁹ R ¹⁰
(Here, 1 represents 0 or 1. R ⁹ and R ¹⁰ are the same or different and each represents a hydrogen atom, a lower alkanoyl group, a lower alkyl group, a morpholinocarbonyl lower alkyl group, a cycloalkylcarbonyl group, a phenyl lower alkenylcarbonyl group, Lower alkylsulfonyl group, aminocarbonyl group which may have a lower alkyl group as a substituent, phenylsulfonyl group which may have a lower alkyl group as a substituent on a phenyl ring, phenyl lower alkenyl group, substituent group on a phenyl ring Has a halogen atom, a lower alkoxy group, an amino group which may have a lower alkanoyl group as a substituent, and a benzoyl group which may have 1 to 3 groups selected from the group consisting of a hydroxyl group, and a lower alkanoyl group as a substituent An amino group-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 be bonded to each other with a nitrogen atom to which is bonded via another nitrogen atom or an oxygen atom, or may be bonded to each other to form a 5- or 6-membered saturated heterocycle.)
Indicates. ); X) group —A ₅ —CR ⁴² R ⁴³ R ⁴⁴ (in the formula, A ₅
Represents a lower alkylene group. R ⁴² and R ⁴³ shall be taken together to form the group = O, the 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-indenyl may have 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 2,3- Dihydro-1H-indenyl group-substituted lower alkyl group; or z) group (In the formula, u represents an integer of 1 to 3.) Is a 5- to 14-membered monocyclic, dicyclic or tricyclic saturated or unsaturated heterocyclic-substituted lower alkenyl group having 1 to 4 heteroatoms selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom. Indicates. R ⁴⁷ is substituted on the above heterocycle, 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 group as a substituent. It may have an aminocarbonyl group that may have an alkyl group, an amino group that may have a lower alkanoyl group as a substituent, a lower alkoxy group as a substituent, and a group selected from the group consisting of halogen atoms on the phenyl ring. Phenyl group or group (Wherein A ₆ , R ⁴⁵ and s are the same as above). ). A) R ³ and R ⁴ may combine with the nitrogen atom to which they are bonded to form a 1,2,3,4-tetrahydroisoquinolyl group. The heterocycle may have a lower alkoxy group as a substituent. However, R ¹
Is a hydrogen atom, R ² is a methyl group, R ³ is a hydrogen atom,
If m represents 0, R ⁴ should not be 2- (imidazolyl-2-yl) ethyl group, 2- (indolyl-3-yl) ethyl group or a sec- butyl group. ] The quinoxaline derivative or its salt represented by these. 2. A 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
Indicates. 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-R ⁵² R ⁵³ (R ⁵²
And R ⁵³ are the same or different and each 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 together with the nitrogen atom to which they are bonded via another nitrogen atom or an oxygen atom to form a 5- or 6-membered saturated heterocycle. E represents a lower alkylene group, a group -C (= O)-or a group -C (= O) -A- (A is a lower alkylene group). ); M) group (In the formula, A is the same as above. R ⁵⁴ represents a hydrogen atom or a lower alkyl group.); N) group (In the formula, A represents a lower alkylene group. P represents an integer of 1 to 3. R ⁵ represents 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 substituted A lower alkoxy group, a lower alkoxy group-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 on the phenyl ring, and a lower alkyl group as a substituent 1,3-dioxolanyl group with 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 −
Indicates. R ⁶ and R ⁷ are the same or different and each represents 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 the phenyl ring, a furyl-substituted lower alkyl group or a lower alkoxy-substituted lower alkyl group is shown. R ⁶ and R ⁷ together with the nitrogen atom to which they are bonded may form a 5- or 6-membered saturated heterocycle with or without a nitrogen atom or an oxygen atom. The heterocycle has 1 to 3 substituents selected from the group consisting of a hydroxyl group, a lower alkyl group and a phenyl lower alkyl group.
You may have one. ). ); O) an amino group or a lower alkoxy group-substituted lower group which may have a lower alkoxy group as a substituent, a halogen atom, a lower alkanoyl group or a phenyl lower alkenylcarbonyl group as a substituent on the phenyl ring. 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 and R ⁴¹ are the same or different and each represents a hydrogen atom or a lower alkyl group. R ⁴⁰ and R ⁴¹ are the same as the nitrogen atom to which they are bonded. May be bonded to each other through a nitrogen atom or an oxygen atom to form a 5- or 6-membered saturated heterocycle), a lower alkenyloxy group, a nitro group and a halogen atom as a substituent. Phenyl lower alkenyl group which may have a group selected from the group consisting of certain lower alkyl groups; p) alkenyl groups; q) cycloalkyl lower alkyl groups; r) naphthyl lower alkyl groups; s) substituents on the phenyl ring A phenylthio-substituted lower alkyl group which may have a lower alkoxy group as; t) a phenyl group which may have a lower alkoxy group as a substituent on the 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, dicyclic or ternary saturated or unsaturated heterocyclic-substituted lower alkyl having 1 to 4 heteroatoms selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom. Indicates a group. R ⁸ is substituted on the above heterocycle, and R ⁸ is
Having a hydrogen atom, an oxo group, a lower alkyl group that may have a hydroxyl group as a substituent, a halogen atom, a nitro group, a lower alkoxy group, a cyano group, a lower alkoxycarbonyl group, or a lower alkanoyl group as a substituent on the 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 the phenyl ring As a lower alkyl group, a lower alkoxy-substituted lower alkoxy group, a hydroxyl group, a halogen atom and a phenyl group which may have a group selected from the group consisting of a lower alkoxy group, a lower alkenyl group, a morpholinocarbonyl lower alkoxy group,
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,
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,
Aminocarbonyl-substituted lower alkyl group that may have a lower alkyl group as a substituent, lower alkoxycarbonyl group-substituted lower alkenyl group, aminocarbonyl-substituted lower alkenyl group that may have a lower alkyl group as a substituent, and carboxy group-substituted lower alkenyl Group, benzoyl group, lower alkoxy lower alkyl group, group (In the formula, s represents an integer of 1 to 3. embedded image Represents a 5- or 6-membered saturated or unsaturated heterocyclic group having 1 to 4 heteroatoms selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom. R ⁴⁵ is substituted on the above heterocycle,
⁴⁵ represents a hydrogen atom, a lower alkyl group, a lower alkoxy lower alkyl group, a phenyl group or an oxo group. ), The group (In the formula, t represents an integer of 1 to 3. Represents a saturated or unsaturated heterocyclic-substituted lower alkyl group of 5 to 6 membered ring having 1 to 4 heteroatoms selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom. R ⁴⁶ is substituted on the heterocyclic ring, R ⁴⁶ represents a hydrogen atom, a lower alkyl group or an oxo group. ), Or a group ^{- (C = O) lNR 9} R 10 ( wherein l is 0 or 1 .R ⁹ and R ¹⁰ are the same or different, a hydrogen atom, a lower alkanoyl group, a lower alkyl group, morpholinocarbonyl Lower alkyl group, cycloalkylcarbonyl group, phenyl lower alkenylcarbonyl group, lower alkylsulfonyl group, aminocarbonyl group which may have a lower alkyl group as a substituent, and lower alkyl group which may have a substituent on the phenyl ring 1 to 3 groups selected from the group consisting of a phenylsulfonyl group, a phenyl lower alkenyl group, a halogen atom as a substituent on the phenyl ring, a lower alkoxy group, an amino group which may have a lower alkanoyl group as a substituent, and a hydroxyl group. A benzoyl group which may have a lower alkanoyl group as a substituent An amino group-substituted lower alkanoyl group,
Amino group which may have a lower alkyl group as a substituent: A substituted sulfonyl group, a phenyl lower alkyl group, a phenyl group or an amino group which may have a lower alkanoyl group as a substituent. R ⁹ and R ¹⁰ may be bonded to each other with a nitrogen atom to which they are bonded via another nitrogen atom or an oxygen atom or not to form a 5- or 6-membered saturated heterocycle. ). ); X) group -A ₅ -CR ⁴² R ⁴³ R ⁴⁴ (wherein A ₅ represents a lower alkylene group. R ⁴² and R ⁴³ together are a group = O, a group = N-
It shall form an OH or 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
A 2,3-dihydro-1H-indenyl group which 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 3-dihydro-1H-indenyl ring. A substituted lower alkyl group; or a z) group (In the formula, u represents an integer of 1 to 3.) Is a 5- to 14-membered monocyclic, dicyclic or tricyclic saturated or unsaturated heterocyclic-substituted lower alkenyl group having 1 to 4 heteroatoms selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom. Indicates. R ⁴⁷ is substituted on the above heterocycle, 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 group as a substituent. It may have an aminocarbonyl group that may have an alkyl group, an amino group that may have a lower alkanoyl group as a substituent, a lower alkoxy group as a substituent, and a group selected from the group consisting of halogen atoms on the phenyl ring. Phenyl group or group (Wherein A ₆ , R ⁴⁵ and s are the same as above). ). A) R ³ and R ⁴ may combine with the nitrogen atom to which they are bonded to form a 1,2,3,4-tetrahydroisoquinolyl group. The heterocycle may have a lower alkoxy group as a substituent. ] A therapeutic agent for diabetes containing at least one compound selected from the quinoxaline derivative represented by the formula and a salt thereof as an active ingredient.