JP2969206B2 - Oxytocin antagonist - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to oxytocin antagonists.

[0002]

BACKGROUND OF THE INVENTION Carbostyril derivatives, which are the active ingredients of the oxytocin antagonist of the present invention, are known compounds having vasopressin antagonistic activity (Japanese Patent Laid-Open No. 3-173).
870). As a result of further studies on the carbostyril derivative, the present inventors have found that the derivative is effective as an oxytocin antagonist. The present invention has been completed based on such findings.

[0003]

The oxytocin antagonist of the present invention contains a carbostil derivative represented by the following general formula (1) or a salt thereof as an organic component.

[0004]

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[Wherein R ¹ represents a hydrogen atom, a nitro group, a lower alkoxy group, a lower alkoxycarbonyl group, a lower alkyl group, a halogen atom, a lower alkanoyl group, a lower alkyl group, a benzoyl group or a phenyl lower alkoxycarbonyl group as a substituent; It represents an amino group, a hydroxyl group, a cyano group, a carboxy group, a lower alkanoyloxy group or a hydrazinocarbonyl group which may have one or two groups selected from the groups. q shows the integer of 1-3. R is a group

[0006]

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[0007] R ² is a hydrogen atom, a lower alkoxycarbonyl group; an amino group or a nitro group which may have one or two groups selected from the group consisting of a lower alkanoyl group, a lower alkyl group and a benzoyl group as a substituent on a phenyl ring. A phenoxycarbonyl group which may have 1 to 3 groups selected from the group; a phenyl lower alkenylcarbonyl group; a phenyl which may have an amino group which may have a lower alkoxycarbonyl group as a substituent on the lower alkanoyl group A lower alkanoyl group; an alkanoyl group; an alkenylcarbonyl group; a phenylsulfonyl group which may have a lower alkoxy group as a substituent on the phenyl ring; a group -CONR ⁸ R ⁹ (wherein R ⁸ and R
⁹ is the same or different, and a group selected from the group consisting of a lower alkoxy group, a lower alkyl group, a halogen atom, a lower alkyl group and a lower alkanoyl group as a substituent on a hydrogen atom or a phenyl ring is 1 to 2; A group selected from the group consisting of an amino group and a nitro group
Indicates a phenyl group which may have three. A heterocyclic carbonyl group (the heterocyclic ring has, as a substituent, one to three groups selected from the group consisting of a phenyl lower alkoxycarbonyl group, a phenyl lower alkoxy group, an oxo group, a lower alkyl group and a lower alkylenedioxy group) May have)
Base

[0008]

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Naphthylcarbonyl group; thienyl lower alkanoyl group; tricyclo [3.3.1.1] decanyl lower alkanoyl group; tricyclo [3.3.1.
1] a decanylcarbonyl group; or a group

[0010]

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(P is 0 or an integer of 1 to 3; R
¹³ is a hydroxyl group; an alkoxy group; a hydroxyl group, a lower alkanoyloxy group, a tri-lower alkylammonium group, a lower alkoxy group and a group -NR ¹⁴ R ¹⁵ (R ¹⁴ and R ¹⁵ are the same or different and are a hydrogen atom, a lower alkyl group A hydroxyl-substituted lower alkyl group, a lower alkanoyl group, a tetrahydropyranyl lower alkyl group, a phenyl group, a phenyl group which may have a hydroxyl group on the lower alkyl group, and which may have a lower alkoxy group as a substituent on the phenyl ring. It represents a lower alkyl group or a pyridyl lower alkyl group.
R ¹⁴ and R ¹⁵ may be bonded together with or without a nitrogen atom, an oxygen atom or a sulfur atom together with the nitrogen atom to which they are bonded to form a 5- to 6-membered saturated heterocyclic ring. . The heterocyclic ring may have a substituent selected from the group consisting of a carbamoyl group, a lower alkyl group, a phenyl lower alkyl group, a phenyl group and a hydroxyl-substituted lower alkyl group. A) an alkoxy group having 1 or 2 groups selected from the group consisting of: a carboxy group-substituted alkoxy group; a halogen-substituted lower alkoxy group; a lower alkoxycarbonyl group-substituted alkoxy group; a lower alkanoyloxy group-substituted lower alkoxy group; a lower alkenyloxy group Substituted lower alkoxy group; lower alkoxy lower alkoxy group; lower alkylsulfonyloxy group substituted lower alkoxy group; benzoyloxy group substituted lower alkoxy group; tricyclo [3.3.1.1] decanyl substituted lower alkoxy group; hydroxyl group and substituent A group selected from the group consisting of amino groups which may have a lower alkyl group as 1 to 2
A morpholinyl-substituted lower alkoxy group which may have a substituent selected from the group consisting of a lower alkyl group and an oxo group;
A benzimidazolylthio-substituted lower alkoxy group; a benzimidazolylsulfinyl-substituted lower alkoxy group;
_{O-A- (E) l -NR} 4 R 5 (A is .E represents an integer of .l 0 or 1 indicating an alkylene group represents a -OCO- group -CO- or a group .R ⁴ and R ⁵ Are the same or different, a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a phenyl lower alkyl group, which may have a hydroxyl group or a cyano group as a substituent, having 1 to 3 halogen atoms as a substituent Sometimes lower alkanoyl group, lower alkyl group as a substituent on the phenyl ring,
A benzoyl group, a phenyl group, or a lower alkoxy group which may have one or two groups selected from the group consisting of a lower alkanoyl group and a phenyl lower alkoxycarbonyl group; A lower alkoxycarbonyl lower alkyl group which may have an amino group which may have a phenyl lower alkoxycarbonyl group as a hydroxyl group or a substituent on a carbonyl group or a lower alkyl group, an amide group which may have a lower alkyl group as a substituent A pyrrolidinylcarbonyl group which may have a phenyl lower alkoxycarbonyl group as a substituent on the pyrrolidine ring, a phenyl lower alkoxycarbonylamino group as a substituent on a lower alkanoyl group, a hydroxyl group, a hydroxyl group as a substituent on the phenyl ring. May have Eniru group, a carbamoyl group, may have a imidazolyl group or a lower alkylthio group,
Further, as a substituent on the amino group, a lower alkyl group which may have a hydroxyl group as a substituent, a lower alkenyl group,
A phenyl lower alkyl group which may have a lower alkoxy group as a substituent on the phenyl ring, a lower alkylsulfonyl group, an amino lower alkanoyl group which may have a lower alkanoyl group or a phenyl lower alkoxycarbonyl group, a hydroxyl-substituted lower alkanoyl group, Lower alkanoyloxy lower alkanoyl group, lower alkylsulfonyl group, lower alkyl group as a substituent on a phenyl ring,
A nitro group, and a phenylsulfonyl group and a lower alkyl group which may have a group selected from an amino group which may have 1 to 2 groups selected from the group consisting of a lower alkyl group and a lower alkanoyl group. It may have a phenyl group, imidazolyl group, carbamoyl group or lower alkylthio group which may have a hydroxyl group as a substituent on a phenyl ring, and may have a lower alkyl group as a substituent on an amide group. Amido lower alkyl group, amino lower alkyl group which may have a group selected from the group consisting of lower alkyl group and lower alkanoyl group as a substituent, anilino carbonyl group, piperidinyl which may have a phenyl lower alkyl group as a substituent Group, cycloalkyl group, cycloalkenylcarbonyl group, cycloal A hydroxyl group and a lower alkanoyloxy group consisting a group selected from the group as a substituent on the Le group 1-3
A cycloalkylcarbonyl group, a tetrahydropyranyl lower alkyl group having 1 to 4 groups selected from the group consisting of a hydroxyl group and a lower alkoxy group as a substituent on a tetrahydropyranyl ring, a pyrrolidinyl, a piperazinyl , A lower alkanoyl group having a 5- to 6-membered saturated heterocyclic ring selected from the group consisting of piperidinyl and morpholinyl groups (the heterocyclic ring has a substituent selected from the group consisting of a lower alkyl group and a phenyl group). A piperidinylcarbonyl group, a lower alkanoyloxy lower alkyl group, a pyridyl lower alkyl group which may have a lower alkanoyl group as a substituent, or an amino acid residue capable of forming an amide group with an amino group bonded thereto. Represents a group. R ⁴ and R ⁵ are bonded together with or without a nitrogen atom, an oxygen atom or a sulfur atom together with the nitrogen atom to which they are bonded to form a 5- or 6-membered saturated or unsaturated heterocyclic ring. You may. In the heterocyclic group, a phenyl group which may have a group selected from the group consisting of a lower alkoxy group and a halogen atom as a substituent on the phenyl ring as a substituent, an oxo group, a hydroxyl group, a lower alkenyl group, a carboxy group, A phenyl lower alkyl group which may have a hydroxyl group on the lower alkyl group, a lower alkanoyl group, a lower alkyl group which may have a hydroxyl group as a substituent, a benzoyl group, an amide group which may have a lower alkyl group as a substituent, It may have a group selected from the group consisting of anilinocarbonyl group, benzoyl lower alkyl group, lower alkylsulfonyl group, piperidinyl group, pyrimidyl group, pyridyl group and lower alkoxycarbonyl group. A carbamoyloxy group-substituted lower alkoxy group; a lower alkylthio-substituted lower alkoxy group; a lower alkylsulfonyl-substituted lower alkoxy group; a lower alkylsulfinyl-substituted lower alkoxy group; an alkenyloxy group; a phenoxy group; a lower alkanoyloxy group; A lower alkynyloxy group, a phenyl lower alkoxy group, a cycloalkyl group, a cycloalkyloxy group, a cycloalkenyloxy group, an imidazo [4,5-c] pyridylcarbonyl lower alkoxy group, a group-(B) ₁ NR ⁶ R ⁷ ( l is the same as above.
B represents a lower alkylene group or a group -CO-. R ⁶ and R ⁷ are the same or different and are a hydrogen atom, a lower alkyl group, a lower alkanoyl group which may have 1 to 3 halogen atoms as a substituent, a carboxy lower alkyl group,
It represents a lower alkoxycarbonyl group, a lower alkoxycarbonyl lower alkyl group, a lower alkenyl group, an amide lower alkyl group which may have a lower alkyl group as a substituent, or a phenyl lower alkoxycarbonyl group. R ⁶ and R ⁷ together with the nitrogen atom to which they are attached,
They may be bonded to each other via a nitrogen atom, an oxygen atom or a sulfur atom with or without a bond to form a 5- or 6-membered saturated or unsaturated heterocyclic ring. The heterocyclic ring may have a lower alkoxycarbonyl group, a lower alkyl group, a lower alkylthio group or an oxo group as a substituent. A nitro group; a halogen atom; a lower alkylsulfonyl group; a lower alkyl group which may have 1 to 3 groups selected from a halogen atom, a hydroxyl group, a phenyl group and a lower alkoxy group as a substituent; An alkoxy group; an oxiranyl-substituted lower alkoxy group; a phthalimide-substituted alkoxy group; an amidino-substituted lower alkoxy group; a pyrrolyl-substituted lower alkoxy group; a cyano group; a lower alkoxycarbonyl group; an amidino group; a carbamoyl group; Lower alkoxycarbonyl lower alkyl group; carboxy lower alkyl group; lower alkoxy lower alkyl group; lower alkanoyloxy lower alkyl group; hydroxyimino lower alkyl group; phenyl group; lower alkylthio group; A lower alkenyl group which may have a hydroxyl group as a substituent; a lower alkylenedioxy group; a lower alkylsilyl group; a pyrimidylthio lower alkoxy group; a pyrimidylsulfinyl lower alkoxy group; a pyrimidylsulfonyl lower alkoxy group; An imidazolylthio lower alkoxy group which may have a lower alkyl group; an imidazolylsulfonyl lower alkoxy group which may have a lower alkyl group as a substituent; a group selected from the group consisting of a lower alkyl group, a lower alkenyl group and an oxo group; Phenylthio lower alkoxy group which may have a group selected from the group consisting of a nitro group and an amino group as a substituent on a phenyl ring; a nitro group as a substituent and a lower group as a substituent on a phenyl ring Alkanoyl And a phenylsulfonyl lower alkoxy group which may have a group selected from the group consisting of an amino group which may have one or two groups selected from the group consisting of a lower alkyl group and an oxo group on a pyridylthio lower alkoxy group or a pyridine ring. Represents a pyridylsulfonyl lower alkoxy group which may have a group. ) N is 1 or 2
And m represents an integer of 0 or 1 to 3, respectively. R ³
Represents a lower alkyl group. R ¹⁰ is a group — (CO) ₁ NR ¹¹
R ¹² (l is the same as above. R ¹¹ and R ¹² are the same or different and are a hydrogen atom, a lower alkyl group, a phenyl lower alkyl group, a lower alkenyl group, a benzoyl group which may have a lower alkoxy group on the phenyl ring, R ¹¹ and R ¹² represent a tricyclo [3.3.1.1] decanyl group, a phenyl group or a cycloalkyl group which may have a lower alkoxy group on the phenyl ring, and R ¹¹ and R ¹² represent a nitrogen atom to which these are bonded. Together with or without a nitrogen, oxygen or sulfur atom to form a saturated or unsaturated heterocyclic ring, wherein the heterocyclic ring is substituted with a benzoyl group, lower alkanoyl group, phenyl A group which may have a substituent selected from the group consisting of a lower alkoxy group and a lower alkanoyl group as a substituent on the lower alkyl group and the phenyl ring. Or a group selected from the group consisting of phenyl and phenyl). The bond at the 3- or 4-position of the carbostyril skeleton represents a single bond or a double bond. However,
R ¹ is a hydrogen atom and the group — (CO) ₁ —NR ¹¹ R ¹²
When 1 in is 0, R ¹¹ and R ¹² must not be simultaneously hydrogen atoms. According to the study of the present inventors, it has been found that the carbostyril derivative represented by the above general formula (1) and a salt thereof all have excellent oxytocin antagonist activity.

The oxytocin antagonist of the present invention has, for example, an inhibitory action on uterine smooth muscle contraction, an inhibitory action on milk release, an inhibitory action on prostaglandin synthesis and release, and a vasodilatory action,
It is effective for prevention or treatment of oxytocin-related diseases, particularly premature labor, dysmenorrhea, and prevention of delivery before cesarean section.

The respective groups represented by the general formula (1) are more specifically as follows.

Examples of the alkoxy group include methoxy, ethoxy, propoxy, isopropoxy, butoxy, tert-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy,
Examples thereof include linear or branched alkoxy groups having 1 to 12 carbon atoms, such as decyloxy, undecyloxy, and dodecyloxy groups.

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

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

The amino group which may have one or two groups selected from a lower alkanoyl group, a lower alkyl group and a benzoyl group as a substituent includes, for example, amino, methylamino, ethylamino, propylamino, isopropylamino Butylamino, tert-butylamino, pentylamino, hexylamino, dimethylamino, diethylamino, dipropylamino, dibutylamino, dipentylamino, dihexylamino, N-methyl-N-ethylamino, N-ethyl-N-propylamino N-methyl-N-butylamino, N-methyl-N-hexylamino, N-methyl-N-acetylamino, N-acetylamino, N-formylamino, N-propionylamino,
N-butyrylamino, N-isobutyrylamino, N-pentanoylamino, N-tert-butylcarbonylamino, N-hexanoylamino, N-ethyl-N-acetylamino, benzoylamino, N-methyl-N-benzoyl A linear or branched alkyl group having 1 to 6 carbon atoms, a linear or branched alkanoyl group having 1 to 6 carbon atoms and a benzoyl group as substituents such as amino and N-ethyl-N-benzoylamino group; And an amino group which may have 1 to 2 groups selected from

Examples of the amino group which may have one or two groups selected from a lower alkanoyl group and a lower alkyl group as a substituent include, for example, amino, methylamino, ethylamino, propylamino, isopropylamino, butylamino Tert-butylamino, pentylamino, hexylamino, dimethylamino, diethylamino, dipropylamino, dibutylamino, dipentylamino, dihexylamino, N-methyl-N-ethylamino, N-
Ethyl-N-propylamino, N-methyl-N-butylamino, N-methyl-N-hexylamino, N-methyl-N-acetylamino, N-acetylamino, N-formylamino, N-propionylamino, N -Butyrylamino, N-isobutyrylamino, N-pentanoylamino, N-tert-butylcarbonylamino, N-hexanoylamino, N-ethyl-N-acetylamino, etc. Examples thereof include an amino group which may have one or two groups selected from a straight or branched chain alkyl group and a straight or branched alkanoyl group having 1 to 6 carbon atoms.

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

A group selected from the group consisting of a lower alkyl group, a phenyl group and a phenyl lower alkyl group as a substituent is 1
Examples of the amino group that may have 2 to 2 include, for example, amino, phenylamino, diphenylamino, methylamino, ethylamino, propylamino, isopropylamino, butylamino, tert-butylamino, pentylamino, hexylamino, dimethylamino, Diethylamino, dipropylamino, dibutylamino, dipentylamino, dihexylamino, N-methyl-N-ethylamino, N-ethyl-N-propylamino, N-methyl-N
-Butylamino, N-methyl-N-hexylamino, N
-Methyl-N-phenylamino, N-ethyl-N-phenylamino, N-benzylamino, N- (2-phenylethyl) amino, N- (1-phenylethyl) amino,
N- (3-phenylpropyl) amino, N- (4-phenylbutyl) amino, N- (5-phenylpentyl) amino, N- (6-phenylhexyl) amino, N-
(1,1-dimethyl-2-phenylethyl) amino, N
-(2-methyl-3-phenylpropyl) amino, N-
As a substituent such as methyl-N-benzylamino, N-ethyl-N-benzylamino, N-phenyl-N-benzylamino, a linear or branched alkyl group having 1 to 6 carbon atoms, phenyl group and alkyl An amino group which may have one or two groups selected from the group consisting of a phenylalkyl group, which is a straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms, can be exemplified.

Examples of a hydroxyl group, a lower alkanoyloxy group, a tri-lower alkylammonium group, a lower alkoxy group and an alkoxy group having one or two groups selected from the group consisting of --NR ¹⁴ R ¹⁵ include hydroxymethoxy,
2-hydroxyethoxy, 1-hydroxyethoxy, 3
-Hydroxypropoxy, 2,3-dihydroxyethoxy, 4-hydroxybutoxy, 3,4-dihydroxybutoxy, 1,1-dimethyl-2-hydroxyethoxy,
5,6-dihydroxyhexyloxy, 5-hydroxypentyloxy, 6-hydroxyhexyloxy, 7-
Hydroxyheptyloxy, 8-hydroxyoctyloxy, 9-hydroxynonyloxy, 10-hydroxydecyloxy, 6- (3,4-dimethoxybenzylamino) -5-hydroxyhexyloxy, 6- (3-methoxybenzylamino)- 5-hydroxyhexyloxy, 6- [2- (2-pyridyl) ethylamino] -5
Hydroxyhexyloxy, 6- [N-methyl-N-
(2-pyridylmethyl) amino] -5-hydroxyhexyloxy, 6- {N-ethyl-N-2- (2-pyridyl) ethyl] amino} -5-hydroxyhexyloxy, 6- [N-ethyl-N -(4-pyridylmethyl) amino] -5-hydroxyhexyloxy, 6- (3-pyridylmethylamino) -5-hydroxyhexyloxy, 6- (2-pyridylmethylamino) -5-hydroxyhexyloxy, 6- (Diethyl, methyl ammonium) -5-methoxyhexyloxy, 4- (trimethyl ammonium) -3-hydroxyhexyloxy, 5-
(Dipropyl, ethyl ammonium) -4-acetyloxypentyloxy, 7- (2-ethoxybenzylamino) -6-acetyloxyheptyloxy, 8- (3,
4,5-trimethoxybenzylamino) -7-ethoxyoctyloxy, 5- [3- (2-pyridyl) propyl] -4-acetyloxypentyloxy, 7- [4-
(3-pyridyl) butyl] -6-propoxyheptyloxy, 2-methyl-3-hydroxypropoxy, aminomethoxy, 1-aminoethoxy, 2-aminoethoxy,
3-aminopropoxy, 4-aminobutoxy, 5-aminopentyloxy, 6-aminohexyloxy, 1,1
-Dimethyl-2-aminoethoxy, 2-methyl-3-aminopropoxy, methylaminomethoxy, ethylaminomethoxy, propylaminomethoxy, isopropylaminomethoxy, butylaminomethoxy, tert-butylaminomethoxy, pentylaminomethoxy, hexylaminomethoxy , Dimethylaminomethoxy, diethylaminomethoxy, dipropylaminomethoxy, dibutylaminomethoxy, dipentylaminomethoxy, dihexylaminomethoxy, N-methyl-N-ethylaminomethoxy, N
-Methyl-N-propylaminomethoxy, N-methyl-
N-butylaminomethoxy, N-methyl-N-hexylaminomethoxy, 1-methylaminoethoxy, 2-ethylaminoethoxy, 3-propylaminopropoxy,
-Butylaminobutoxy, 1,1-dimethyl-2-pentylaminoethoxy, 5-hexylaminopentyloxy, 6-dimethylaminohexyloxy, 7-methylaminoheptyloxy, 8-dimethylaminooctyloxy, 4-dimethylaminobutoxy , 2-diethylaminoethoxy, 1- (N-methyl-N-hexylamino) ethoxy, 3-dihexylaminopropoxy, 6-diethylaminohexyloxy, 4-dibutylaminobutoxy, 9- (N-methyl-N-propylamino) Nonyloxy, 2- (N-methyl-N-pentylamino) ethoxy, 7-hydroxy-8-dimethylaminooctyloxy, 2-hydroxy-3-diethylaminopropoxy,
7-hydroxy-8-diethylaminooctyloxy,
2-hydroxy-3- (N-phenyl-N-benzylamino) propoxy, 7-hydroxy-8-ethylaminooctyloxy, 3-hydroxy-4-methylaminobutoxy, 5-hydroxy-6-diethylaminohexyloxy, 3 -Hydroxy-4-phenylaminobutoxy, 8-hydroxy-9-dimethylaminononyloxy, 4-hydroxy-5-dimethylaminopentyloxy, 9-hydroxy-10-diethylaminodecyloxy, 4-hydroxy-5-methylaminopentyl Oxy, 4-hydroxy-5-diethylaminopentyloxy, phenylaminomethoxy, diphenylaminomethoxy, benzylaminomethoxy, 5-hydroxy-6-benzylaminohexyloxy, 5-hydroxy-6
[N-methyl-N- (2-phenylethyl) amino] hexyloxy, 5-hydroxy-6-ethylaminohexyloxy, 5-hydroxy-6-isopropylaminohexyloxy, 5-hydroxy-6- (N-methyl −
(N-benzylamino) hexyloxy, 5-hydroxy-6-aminohexyloxy, (N-methyl-N-benzylamino) methoxy, (N-ethyl-N-benzylamino) methoxy, (N-phenyl-N-benzyl) Amino) methoxy, 2- (phenylamino) ethoxy, 3-
(2-phenylethylamino) propoxy, 4- (3-
Phenylpropylamino) butoxy, 1,1-dimethyl-2- (4-phenylbutylamino) ethoxy, 5-
(5-phenylpentylamino) pentyloxy, 6-
(6-phenylhexylamino) hexyloxy, 7-
Hydroxy-8- (N-phenyl-N-benzylamino) octyloxy, 8-hydroxy-9- [N- (2
-Phenylethyl) amino] nonyloxy, 9-hydroxy-10- (N-ethyl-N-benzylamino) decyloxy, acetyloxymethoxy, 2-propionyloxyethoxy, 1-butyryloxyethoxy, 3-acetyloxypropoxy, -Isobutyryloxybutoxy, 5-pentanoyloxypentyloxy, 6-te
rt-butylcarbonyloxyhexyloxy, 1,1-
Dimethyl-2-hexanoyloxyethoxy, 2-methyl-3-acetyloxypropoxy, 7-acetyloxyheptyloxy, 8-acetyloxyoctyloxy, 9-acetyloxynonyloxy, 10-acetyloxydecyloxy, (hydroxymethyl ) Aminomethoxy, 1- [N, N-di- (2-hydroxyethyl) amino] ethoxy, 2- (3-hydroxypropyl) aminoethoxy, 3- (4-hydroxybutyl) aminopropoxy, 4- (5- (Hydroxypentyl) aminobutoxy, 5- (6-hydroxyhexyl) aminopentyloxy, 6- [N- (2-hydroxyethyl) -N-methylamino] hexyloxy, 5-hydroxy-6- [N
-(2-hydroxyethyl) -N-methylamino] hexyloxy, 5-hydroxy-6- [N, N-di (2-
(Hydroxyethyl) amino] hexyloxy, 6-hydroxy-7- [N- (2-hydroxyethyl) -N-benzylamino] heptyloxy, 7-hydroxy-8-
[N- (3-hydroxypropyl) -N-phenylamino] octyloxy, 7-hydroxy-9- {N- (4
-Hydroxybutyl) -N-[(tetrahydropyranyl-2-yl) methyl] amino} nonyloxy, 8-hydroxy-10- [N- (2-hydroxyethyl) -N-
[Acetylamino] decyloxy, acetylaminomethoxy, 2- (formylamino) ethoxy, 1- (propionylamino) ethoxy, 3- (butyrylamino) propoxy, 4- (isobutyrylamino) butoxy, 5- (pentanoylamino) pentyl Oxy, 6- (hexanoylamino) hexyloxy, 5-acetyloxy-6-
Acetylaminohexyloxy, 5-hydroxy-6
Acetylaminohexyloxy, 6-hydroxy-7-
(N-methyl-N-acetylamino) heptyloxy,
7-hydroxy-8- (N-benzyl-N-acetylamino) octyloxy, 8-hydroxy-9- (N-phenyl-N-acetylamino) nonyloxy, 9-acetyloxy-10- [N- (tetrahydro- 2-pyranylmethyl) -N-acetylamino] decyloxy, (tetrahydro-2-pyranyl) methylaminomethoxy,
-(Tetrahydro-3-pyranylmethylamino) ethoxy, 1- (tetrahydro-4-pyranylmethylamino)
Ethoxy, 3- [2- (tetrahydro-2-pyranyl)
Ethylamino] propoxy, 4- [3- (tetrahydro-2-pyranyl) propylamino] butoxy, 5- [4
-(Tetrahydro-2-pyranyl) butylamino] pentyloxy, 5-hydroxy-6- [N-ethyl-N-
Tetrahydro-2-pyranylmethylamino] hexyloxy, 6-hydroxy-7- {N-phenyl-N- [5
-(Tetrahydro-2-pyranyl) pentylamino} heptyloxy, 7-hydroxy-8- {N-benzyl-
N- [6- (tetrahydro-2-pyranyl) hexylaminodioctyloxy, (2-hydroxy-2-phenylethyl) aminomethoxy, 2-[(3-hydroxy-
3-phenylpropyl) amino] ethoxy, 3-[(2
-Hydroxy-4-phenylbutyl) amino] propoxy, 4-[(6-hydroxy-6-phenylhexyl)
Amino] butoxy, 5-[(2-hydroxy-2-phenylethyl) amino] pentyloxy, 5-hydroxy-6-[(2-hydroxy-2-phenylethyl) amino] hexyloxy, 6-hydroxy-7- [N- (2
-Hydroxy-2-phenylethyl) -N-methylamino] heptyloxy, 7-hydroxy-8- [N- (2
-Hydroxy-2-phenylethyl) -N-phenylamino] octyloxy, 8-hydroxy-9- [N-
(2-hydroxy-2-phenylethyl) -N-benzylamino] nonyloxy, 9-hydroxy-10- [N
-(2-hydroxy-2-phenylethyl) -N-acetylamino] decyloxy, (piperazin-1-yl)
Methoxy, 2- (pyrrolidin-1-yl) ethoxy, 3
-(Piperidin-1-yl) propoxy, 4-morpholinoboxy, 5-thiomorpholinopentyloxy, 6-
(Piperazin-1-yl) hexyloxy, 5-hydroxy-6- (4-benzyl-1-piperazinyl) hexyloxy, 5-hydroxy-6- (1-piperazinyl)
Hexyloxy, 5-hydroxy-6- (4-methyl-
1-piperazinyl) hexyloxy, 4-hydroxy-
5- (1-pyrrolidinyl) pentyloxy, 4-hydroxy-5- (1-piperidinyl) pentyloxy, 4-
Hydroxy-5-morpholinopentyloxy, 5-hydroxy-6- (1-pyrrolidinyl) hexyloxy, 5
-Hydroxy-6- (1-piperidinyl) hexyloxy, 5-hydroxy-6- (4-phenyl-1-piperazinyl) hexyloxy, 5-hydroxy-6- (2-
Carbamoyl-1-pyrrolidinyl) hexyloxy, 7
-Hydroxy-8- (1-pyrrolidinyl) octyloxy, 5-hydroxy-6- (2-hydroxymethyl-1
-Pyrrolidinyl) hexyloxy, 7- (2-carbamoylmorpholino) -6-hydroxyheptyloxy, 8
-Hydroxy-9- (4-benzyl-1-piperazinyl) nonyloxy, 4- (3-carbamoyl-1-piperidinyl) -3-humanoxybutoxy, 9-hydroxy-10- (4-ethyl-1-piperazinyl) decyloxy , 6- (4-carbamoyl-1-piperazinyl) -5
-A hydroxyl group such as a hydroxyhexyloxy group, having 1 to 1 carbon atoms;
A straight-chain or branched alkanoyloxy group of 6; a trialkylammonium group which is a straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms in the alkyl portion; a straight-chain or branched chain of 1 to 6 carbon atoms A chain alkoxy group and a group —NR ¹⁴ R ¹⁵ (R
¹⁴ and R ¹⁵ are the same or different and each are a hydrogen atom,
A straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms, a straight-chain or branched-chain alkanoyl group having 1 to 6 carbon atoms, and a hydroxyl group in which the alkyl portion is a straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms A substituted alkyl group, a tetrahydropyranylalkyl group in which the alkyl portion is a linear or branched alkyl group having 1 to 6 carbon atoms, a phenyl group, a hydroxyl group may be present on the alkyl group, and A phenylalkyl group having 1 to 6 carbon atoms as a group, wherein the alkyl moiety may have 1 to 3 linear or branched alkoxy groups, It represents a pyridylalkyl group which is a linear or branched alkyl group having 1 to 6 carbon atoms in the alkyl portion. R ¹⁴ and R ¹⁵ are, together with the nitrogen atom to which they are bound, bonded to each other via a nitrogen atom, an oxygen atom or a sulfur atom, or
A 6- to 6-membered saturated heterocyclic ring may be formed. On the heterocyclic ring, a carbamoyl group as a substituent, a linear or branched alkyl group having 1 to 6 carbon atoms, and an alkyl moiety having 1 to 6 carbon atoms.
A phenylalkyl group which is a straight-chain or branched alkyl group of 6, a phenyl group and a hydroxyl-substituted alkyl group whose alkyl portion is a straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms. It may have 1 to 3 groups. )
1 to 10 carbon atoms having 1 to 2 groups selected from the group consisting of
Can be exemplified.

As the carboxy-substituted alkoxy group,
For example, carboxymethoxy, 2-carboxyethoxy, 1-carboxyethoxy, 3-carboxypropoxy, 4-carboxybutoxy, 5-carboxypentyloxy, 6-carboxyhexyloxy, 1,1-dimethyl-2-carboxyethoxy, 2-carboxyethoxy Methyl-3-carboxypropoxy, 7-carboxyheptyloxy, 8
Linear or branched alkoxy having 1 to 12 carbon atoms in the alkoxy moiety such as -carboxyoctyloxy, 9-carboxynonyloxy, 10-carboxydecyloxy, 11-carboxyundecyloxy, 12-carboxydodecyloxy and the like; And a carboxyalkoxy group as a group.

The lower alkoxycarbonyl-substituted alkoxy group includes, for example, methoxycarbonylmethoxy, 3
-Methoxycarbonylpropoxy, ethoxycarbonylmethoxy, 3-ethoxycarbonylpropoxy, 4-ethoxycarbonylbutoxy, 5-isopropoxycarbonylpentyloxy, 6-propoxycarbonylhexyloxy, 1,1-dimethyl-2-butoxycarbonylethoxy, 2- Methyl-3-tert-butoxycarbonylpropoxy, 2-pentyloxycarbonylethoxy,
Hexyloxycarbonylmethoxy, 7-methoxycarbonylheptyloxy, 8-ethoxycarbonyloctyloxy, 9-propoxycarbonylnonyloxy, 1
An alkoxycarbonyl moiety such as a 0-butoxycarbonyldecyloxy, 11-methoxycarbonylundecyloxy, or 12-ethoxycarbonyldodecyloxy group is a linear or branched alkoxycarbonyl group having 1 to 6 carbon atoms; Twelve straight-chain or branched alkoxycarbonylalkoxy groups can be mentioned.

The lower alkanoyloxy group-substituted lower alkoxy group includes, for example, acetyloxymethoxy,
Propionyloxyethoxy, 1-butyryloxyethoxy, 3-acetyloxypropoxy, 4-isobutyryloxybutoxy, 5-pentanoyloxypentyloxy, 6-tert-butylcarbonyloxyhexyloxy, 1,1-dimethyl-2 A straight-chain or branched alkanoyloxy group having 2 to 6 carbon atoms, such as a hexanoyloxyethoxy or 2-methyl-3-acetyloxypropoxy group; a straight-chain or branched alkoxy group having 1 to 6 carbon atoms; Can be mentioned.

The lower alkenyloxy group-substituted lower alkoxy group includes, for example, vinyloxymethoxy, 2-allyloxyethoxy, 1- (2-butenyloxy) ethoxy, 3-allyloxypropoxy, 4- (3-butenyloxy) butoxy, -(1-methylallyloxy) pentyloxy, 6- (2-pentenyloxy) hexyloxy, 1,1-dimethyl-2- (2-hexenyloxy) ethoxy, 2-methyl-3-allyloxypropoxy and the like A straight-chain or branched alkenyloxy group having 2 to 6 carbon atoms may be a straight-chain or branched-chain alkoxy group having 1 to 6 carbon atoms.

The lower alkoxy group includes, for example, methoxymethoxy, 3-methoxypropoxy, 4-ethoxybutoxy, 6-propoxyhexyloxy, 5-isopropoxypentyloxy, 1,1-dimethyl-2-butoxyethoxy, -Methyl-3-tert
-Butoxypropoxy, 2-pentyloxyethoxy,
A straight-chain or branched-chain alkoxy group having 1 to 6 carbon atoms such as a hexyloxymethoxy group may be a straight-chain or branched-chain alkoxy group having 1 to 6 carbon atoms.

The lower alkylsulfonyloxy group-substituted lower alkoxy groups include, for example, methylsulfonyloxymethoxy, 3-methylsulfonyloxypropoxy,
-Ethylsulfonyloxybutoxy, 2-methylsulfonyloxyethoxy, 6-propylsulfonyloxyhexyloxy, 5-isopropylsulfonyloxypentyloxy, 1,1-dimethyl-2-butylsulfonyloxyethoxy, 2-methyl-3-methylsulfonyl A linear or branched alkylsulfonyloxy group having 1 to 6 carbon atoms, such as an oxypropoxy group, may be a linear or branched alkoxy group having 1 to 6 carbon atoms.

Examples of the benzoyloxy group-substituted lower alkoxy group include benzoyloxymethoxy, 2-benzoyloxyethoxy, 1-benzoyloxyethoxy, 3-benzoyloxypropoxy, 4-benzoyloxybutoxy, 6-benzoyloxyhexyloxy, -Benzoyloxypentyloxy, 1,1-dimethyl-2-benzoyloxyethoxy, 2-methyl-
A benzoyloxyalkoxy group in which an alkoxy moiety such as a 3-benzoyloxypropoxy group is a linear or branched alkoxy group having 1 to 6 carbon atoms can be given.

Examples of the tricyclo [3.3.1.1] decanyl-substituted lower alkoxy group include tricyclo [3.3.1.1] decanylmethoxy and 2-tricyclo [3.3.1.1]. ] Decanylethoxy, 1-tricyclo [3.3.1.1] decanylethoxy, 3-tricyclo [3.3.1.1] decanylpropoxy, 4-tricyclo [3.3.1. 1] decanyl butoxy, 5-
Tricyclo [3.3.1.1] decanylpentyloxy, 6-tricyclo [3.3.1.1] decanylhexyloxy, 1,1-dimethyl-2-tricyclo [3.3.1 .1] decanylethoxy, 2-methyl-3
Tricyclo [3.3.1.1] decanylpropoxy group and other tricyclo [3.3.1.1] decanyl straight-chain or branched alkoxy groups having 1 to 6 carbon atoms. it can.

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

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

Examples of the amino group which may have one or two groups selected from the group consisting of a lower alkyl group, a lower alkanoyl group and a phenyl lower alkoxycarbonyl group include amino, methylamino, ethylamino, propyl Amino, isopropylamino, butylamino, tert-butylamino, pentylamino, hexylamino, dimethylamino, diethylamino, dipropylamino, dibutylamino, dipentylamino, dihexylamino, N-methyl-N-ethylamino, N-ethyl-
N-propylamino, N-methyl-N-butylamino,
N-methyl-N-hexylamino, N-benzyloxycarbonylamino, N- (2-phenylethoxycarbonyl) amino, N- (1-phenylethoxycarbonyl) amino, N- (3-phenylpropoxycarbonyl) amino, N- -(4-phenylbutoxycarbonyl)
Amino, N- (5-phenylpentyloxycarbonyl) amino, N- (6-phenylhexyloxycarbonyl) amino, N- (1,1-dimethyl-2-phenylethoxycarbonyl) amino, N- (2-methyl- 3-
Phenylpropoxycarbonyl) amino, N-methyl-
N-benzyloxycarbonylamino, N-ethyl-N
-Benzyloxycarbonylamino, acetylamino,
Formylamino, propionylamino, butyrylamino, isobutyrylamino, pentanoylamino, tert-
A straight chain having 1 to 6 carbon atoms as a substituent such as butylcarbonylamino, hexanoylamino, N-methyl-N-acetylamino, N-ethyl-N-acetylamino, N-benzyloxycarbonyl-N-acetylamino; Or a phenylalkoxycarbonyl group in which a branched alkyl group, a linear or branched alkanoyl group having 1 to 6 carbon atoms and an alkoxy moiety is a linear or branched alkoxy group having 1 to 6 carbon atoms. An amino group which may have one or two groups selected from the above can be exemplified.

A substituent selected from the group consisting of an amino group and a nitro group which may have one or two groups selected from the group consisting of a lower alkyl group, a lower alkanoyl group and a phenyl lower alkoxycarbonyl group on the phenyl ring. The benzoyl group which may have a group includes, for example, benzoyl, 2-aminobenzoyl, 4-aminobenzoyl,
-Methylaminobenzoyl, 3-ethylaminobenzoyl, 2- (N-methyl-N-ethylamino) benzoyl, 3- (N-methyl-N-hexylamino) benzoyl, 4-dimethylaminobenzoyl, 4-dipentylaminobenzoyl , 2-isopropylaminobenzoyl,
3-butylaminobenzoyl, 4- (N-methyl-N-
Benzyloxycarbonylamino) benzoyl, 2-
[N- (2-phenylethoxycarbonyl) amino] benzoyl, 2,3-bis (dimethylamino) benzoyl, 3,4-bis (methylamino) benzoyl,
4,5-tri (methylamino) benzoyl, 2,6-di (N-methyl-N-benzyloxycarbonylamino)
Benzoyl, 3- [N- (3-phenylpropoxycarbonyl) amino] benzoyl, 4- [N- (5-phenylpentyloxycarbonyl) amino] benzoyl,
-[N- (6-phenylhexyloxycarbonyl) amino] benzoyl, 3- [N- (4-phenylbutoxycarbonyl) amino] benzoyl, 4-acetylaminobenzoyl, 3- (N-methyl-N-acetylamino)
Benzoyl, 2- (N-benzyloxycarbonyl-N
-Acetylamino) benzoyl, 4-nitrobenzoyl, 4-nitro-3-methylaminobenzoyl, 2,4
-A linear or branched alkyl group having 1 to 6 carbon atoms, a linear or branched chain having 1 to 6 carbon atoms as a substituent on a phenyl ring such as dinitrobenzoyl or 2,4,6-trinitrobenzoyl group; A group selected from the group consisting of a phenylalkoxycarbonyl group, which is a linear or branched alkoxy group having 1 to 6 carbon atoms in the chain alkanoyl group and the alkoxy moiety,
And a benzoyl group which may have 1 to 3 groups selected from the group consisting of an amino group and a nitro group.

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

Examples of the lower alkoxycarbonyl lower alkyl group include methoxycarbonylmethyl, 3-methoxycarbonylpropyl, ethoxycarbonylmethyl,
4-ethoxycarbonylbutyl, 1-ethoxycarbonylethyl, 1-methoxycarbonylethyl, 6-propoxycarbonylhexyl, 5-isopropoxycarbonylpentyl, 1,1-dimethyl-2-butoxycarbonylethyl, 2-methyl-3-tert An alkyl moiety such as -butoxycarbonylpropyl, 2-pentyloxycarbonylethyl, hexyloxycarbonylmethyl or the like having 1 to 6 carbon atoms having a linear or branched alkyl group;
To 6 linear or branched alkoxycarbonylalkyl groups.

Amide groups which may have a lower alkyl group as a substituent include, for example, carbamoyl, methylamide, ethylamide, propylamide, isopropylamide, butylamide, tert-butylamide, pentylamide, hexylamide, dimethylamide, diethylamide, diamide Propylamide, dibutylamide, dipentylamide, dihexylamide, N-methyl-N-ethylamide, N-ethyl-N-propylamide, N-methyl-
Examples of the substituent such as an N-butylamide and an N-methyl-N-hexylamide group include an amide group which may have 1 to 2 linear or branched alkyl groups having 1 to 6 carbon atoms.

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

Along with the nitrogen atom to which R ⁴ and R ⁵ are attached,
Examples of the 5- or 6-membered saturated or unsaturated heterocyclic ring formed by bonding to each other through or without a nitrogen atom, an oxygen atom or a sulfur atom include, for example, pyrrolidinyl, piperidinyl, piperazinyl, morpholino, thiomorpholino, pyrrolyl, Pyrazolyl, imidazolyl, imidazolidinyl,
1,2,4-triazolyl, 1,2,3,4-tetrazolyl, pyrrolinyl, imidazolinyl, pyrazolinyl, pyrazolidinyl, oxazolidinyl, oxazolinyl, isoxazolinyl, isoxazolidinyl, thiazolinyl, thiazolidinyl, isothiazolinyl, isothiazolidinyl And the like.

Examples of the phenyl group which may have a substituent selected from the group consisting of a lower alkoxy group and a halogen atom on the phenyl ring include phenyl, 2-methoxyphenyl, 3-methoxyphenyl, and 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-difluoro Phenyl, 3,5-dibromophenyl, 3,
As a substituent on a phenyl ring such as a 4,5-trichlorophenyl or 2-methoxy-3-chlorophenyl group, one having 1 carbon atom
And a phenyl group which may have from 1 to 6 straight or branched alkoxy groups and 1 to 3 groups selected from the group consisting of halogen atoms.

A hydroxyl group on a phenyl group, an oxo group, a hydroxyl group, a lower alkenyl group, a carboxy group or a lower alkyl group which may have a substituent selected from the group consisting of a lower alkoxy group and a halogen atom on the phenyl ring. Phenyl lower alkyl group which may have, lower alkanoyl group, lower alkyl group which may have a hydroxyl group as a substituent, benzoyl group, amide group which may have a lower alkyl group as a substituent, anilino carbonyl group, benzoyl lower Alkyl group, lower alkylsulfonyl group,
Examples of the heterocyclic group substituted by a group selected from the group consisting of piperidinyl group, pyrimidyl group, pyridyl group and lower alkoxycarbonyl group include 4-phenylpiperazinyl,
-(4-methoxyphenyl) piperazinyl, 4- (4-
(Chlorophenyl) piperazinyl, 3- (2-ethoxyphenyl) pyrrolidinyl, 2- (4-isopropoxyphenyl) pyrrolidinyl, 4- (4-pentyloxyphenyl) piperidinyl, 3- (4-hexyloxyphenyl) piperidinyl, 3- ( 2,3-dimethoxyphenyl) morpholino, 2- (2-methoxyphenyl) morpholino, 3- (3-ethoxyphenyl) thiomorpholino,
2- (3,4,5-trimethoxyphenyl) thiomorpholino, 4- (3,4-dimethoxyphenyl) piperazinyl, 4- (3,4,5-trimethoxyphenyl) piperazinyl, 3- (2-fluorophenyl ) Pyrrolidinyl,
2- (3-bromophenyl) pyrrolidinyl, 4- (3-
Iodophenyl) piperidinyl, 3- (4-bromophenyl) piperidinyl, 2- (3,4-dichlorophenyl) morpholino, 3- (3-chlorophenyl) morpholino, 3- (2-bromophenyl) thiomorpholino, 2-
(4-fluorophenyl) thiomorpholino, 4- (3,
4,5-trichlorophenyl) piperazinyl, 4-
(2,6-dichlorophenyl) piperazinyl, 4-benzylpiperazinyl, 3- (2-phenylethyl) pyrrolidinyl, 2- (3-phenylpropyl) pyrrolidinyl,
4- (4-phenylbutyl) piperidinyl, 3- (5-
Phenylpentyl) morpholino, 2- (6-phenylhexyl) thiomorpholino, 4- (2-phenyl-2-hydroxyethyl) piperazinyl, 3- (1-hydroxy-1-phenylmethyl) pyrrolidinyl, 2- (3-hydroxy -3-phenylpropyl) pyrrolidinyl, 4-
(2-hydroxy-4-phenylbutyl) piperidinyl, 2- (5-hydroxy-5-phenylpentyl) thiomorpholino, 3- (6-hydroxy-6-phenylhexyl) morpholino, 4-acetylpiperazinyl,
Formylpyrrolidinyl, 2-propionylpyrrolidinyl, 4-butyrylpiperidinyl, 3-pentanoylthiomorpholino, 2-hexanoylmorpholino, 4-methylpiperazinyl, 3,4-dimethylpiperazinyl, 3- Ethylpyrrolidinyl, 2-propylpyrrolidinyl, 3,
4,5-trimethylpiperidinyl, 4-butylpiperidinyl, 3-pentylmorpholino, 2-hexylthiomorpholino, 4-benzoylpiperazinyl, 3-benzoylpyrrolidinyl, 3-benzoylmorpholino, 2-benzoylthio Morpholino, 3-benzoylpiperidinyl, 4
-Anilinocarbonylpiperazinyl, 2-anilinocarbonylpyrrolidinyl, 3-anilinocarbonylpiperidinyl, 2-anilinocarbonylmorpholino, 3-anilinocarbonylthiomorpholino, 4- (benzoylmethyl) piperazinyl, -(1-benzoylethyl) pyrrolidinyl, 2- (3-benzoylpropyl) pyrrolidinyl, 4- (4-benzoylbutyl) piperidinyl, 3-
(5-benzoylpentyl) morpholino, 2- (6-benzoylhexyl) thiomorpholino, 3-methyl-4-
Benzoylpiperazinyl, 3-ethyl-4-acetylpiperidinyl, 3-methyl-4-benzylpyrrolidinyl,
3-propyl-4-anilinocarbonylpyrrolidinyl,
3-methyl-5- (benzoylmethyl) morpholino, 3
-Methyl-5- (2-phenyl-2-hydroxyethyl) thiomorpholino, 4-methylsulfonylpiperazinyl, 4-methoxycarbonylpiperazinyl, 3-ethylsulfonylpyrrolidinyl, 3-ethoxycarbonylpyrrolidinyl, 4-propylsulfonylpiperidinyl, 3-
Propoxycarbonylpiperidinyl, 3-butylsulfonylmorpholino, 2-pentyloxycarbonylmorpholino, 2-hexylsulfonylthiomorpholino, 3-hexyloxycarbonylthiomorpholino, 4-allylpiperazinyl, 4-ethoxycarbonylpiperidinyl, 4
-Carboxypiperidinyl, 4-dimethylamidopiperidinyl, 4-carbamoylpiperidinyl, 4- (1-piperidinyl) piperidinyl, 3-hydroxypiperidinyl, 2-carbamoylpyrrolidinyl, 2-hydroxymethylpiperidinyl 2-hydroxymethylpyrrolidinyl, 3-hydroxymethylpiperidinyl, 3-hydroxypyrrolidinyl, 4- (2-hydroxyethyl) piperidinyl, 2-methoxycarbonylpyrrolidinyl, 2-
(2-hydroxyethyl) piperidinyl, (2-pyrimidyl) piperazinyl, (2-pyridyl) piperazinyl,
4-oxothiomorpholino, 4,4-dioxothiomorpholino, 2-methylimidazolyl, 3-methyl-1,
2,4-triazolyl, 5-methyl-1,2,3,4-
Tetrazolyl, 4-hydroxymethylimidazolyl, 3
-Allyl-1,2,4-triazolyl, 5-phenyl-
A straight chain having 1 to 6 carbon atoms as a substituent on a phenyl ring such as 1,2,3,4-tetrazolyl, 3-carboxypyrrolyl, 2-hydroxyoxazolidinyl, 2-carbamoylthiazolidinyl or the like; A phenyl group, an oxo group, a hydroxyl group, a linear or branched alkenyl group having 2 to 6 carbon atoms, which may have 1 to 3 groups selected from the group consisting of a branched alkoxy group and a halogen atom; A phenylalkyl group which is a linear or branched alkyl group having 1 to 6 carbon atoms in the alkyl moiety which may have a hydroxyl group on the alkyl group, a linear or branched alkyl group having 1 to 6 carbon atoms An alkanoyl group, a linear or branched alkyl group having 1 to 6 carbon atoms which may have 1 to 3 hydroxyl groups as a substituent, a benzoyl group, a linear or branched chain having 1 to 6 carbon atoms as a substituent Alkyl groups of 1 to 2 An amide group, anilinocarbonyl group, a benzoylalkyl group in which the alkyl moiety is a straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms, a straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms. Sulfonyl group,
Examples of the above-mentioned heterocyclic group in which 1 to 3 groups selected from the group consisting of a piperidinyl group, a pyrimidyl group, a pyridyl group and a linear or branched alkoxycarbonyl group having 1 to 6 carbon atoms are substituted.

The phenyl lower alkyl group which may have a hydroxyl group on the lower alkyl group and may have a lower alkoxy group as a substituent on the phenyl ring includes, for example, 1-
Hydroxy-1-phenylmethyl, 1-phenyl-2-
Hydroxyethyl, 2-phenyl-2-hydroxyethyl, 3-hydroxy-3-phenylpropyl, 2-hydroxy-4-phenylbutyl, 6-hydroxy-6-phenylhexyl, 3,4-dimethoxybenzyl, 3-methoxybenzyl , 1- (2-methoxyphenyl) ethyl, 2- (4-methoxyphenyl) ethyl, 3- (2-
Ethoxyphenyl) propyl, 4- (3-ethoxyphenyl) butyl, 5- (4-ethoxyphenyl) pentyl, 6- (4-isopropoxyphenyl) hexyl,
1,1-dimethyl-2- (4-pentyloxyphenyl) ethyl, 2-methyl-3- (4-hexyloxyphenyl) propyl, 3-ethoxy-4-methoxybenzyl, 2,3-dimethoxybenzyl, 4-diethoxybenzyl, 3,4,5-trimethoxybenzyl, 1-hydroxy-1- (3-methoxyphenyl) methyl, 1-
Alkyl groups such as (2,5-dimethoxyphenyl) -2-hydroxyethyl, 2- (2,6-dimethoxyphenyl) -2-hydroxyethyl, 5-hydroxy-5- (3,4-dipentyloxy) pentyl May have a hydroxyl group on the phenyl ring, and an 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 has 1 to 6 carbon atoms. A phenylalkyl group which is a linear or branched alkyl group can be exemplified.

Examples of the benzoyl lower alkyl group include, for example, benzoylmethyl, 1-benzoylethyl, 2-benzoylethyl, 3-benzoylpropyl, 4-benzoylbutyl, 5-benzoylpentyl, 6-benzoylhexyl, 1,1-dimethyl- 2-benzoylethyl, 2
And a benzoylalkyl group in which the alkyl moiety such as -methyl-3-benzoylpropyl group is a linear or branched alkyl group having 1 to 6 carbon atoms.

As the carbamoyloxy group-substituted lower alkoxy group, for example, carbamoyloxymethoxy, 2-carboxy
Carbamoyloxyethoxy, 1-carbamoyloxyethoxy, 3-carbamoyloxypropoxy, 4-carbamoyloxybutoxy, 5-carbamoyloxypentyloxy, 6-carbamoyloxyhexyloxy, 1,1-dimethyl-2-carbamoyloxyethoxy, 2- Examples thereof include a carbamoyloxyalkoxy group in which an alkoxy moiety such as a methyl-3-carbamoyloxypropoxy group is a linear or branched alkoxy group having 1 to 6 carbon atoms.

Examples of the lower alkylthio-substituted lower alkoxy group include methylthiomethoxy, 3-ethylthiopropoxy, 4-methylthiobutoxy, 2-methylthioethoxy, 6-propylthiohexyloxy, 5-isopropylthiopentyloxy, 1,1- C1-C6 linear or branched alkylthio group such as dimethyl-2-butylthioethoxy, 2-methyl-3-methylthiopropoxy group, etc. Substituted C1-C6 linear or branched alkoxy group Can be mentioned.

As the lower alkylsulfonyl-substituted lower alkoxy group, for example, methylsulfonylmethoxy, 3-
Ethylsulfonylpropoxy, 4-methylsulfonylbutoxy, 2-methylsulfonylethoxy, 6-propylsulfonylhexyloxy, 5-isopropylsulfonylpentyloxy, 1,1-dimethyl-2-butylsulfonylethoxy, 2-methyl-3-methylsulfonyl A linear or branched alkylsulfonyl group having 1 to 6 carbon atoms, such as a propoxy group, may be a linear or branched alkoxy group having 1 to 6 carbon atoms.

The lower alkylsulfinyl-substituted lower alkoxy group includes, for example, methylsulfinylmethoxy,
3-ethylsulfinylpropoxy, 4-methylsulfinylbutoxy, 2-methylsulfinylethoxy, 6
-Propylsulfinylhexyloxy, 5-isopropylsulfinylpentyloxy, 1,1-dimethyl-
A linear or branched alkylsulfinyl group having 1 to 6 carbon atoms such as 2-butylsulfinylethoxy, 2-methyl-3-methylsulfinylpropoxy group, etc.
A straight-chain or branched-chain alkoxy group.

Examples of the alkenyloxy group include vinyloxy, allyloxy, 3-methyl-2-butenyloxy, 2-butenyloxy, 3-butenyloxy, 1-
Methylallyloxy, 2-pentenyloxy, 2-hexenyloxy, 1-heptenyloxy, 1-octenyloxy, 1-nonenyloxy, 1-decenyloxy, 1
-Undecenyloxy, 1-dodecenyloxy, 2-heptenyloxy, 3-heptenyloxy, 2-methyl-
4-heptenyloxy, 2-methyl-5-heptenyloxy, 4-methyl-2-heptenyloxy, 3-methyl-1-heptenyloxy, 1,3-heptadienyloxy, 1,4-heptadienyloxy, 1,5- Heptadienyloxy, 1,6-heptadienyloxy, 2,4
-Heptadienyloxy, 2-methyl-2,4-heptadienyloxy, 2,6-dimethyl-2,4-heptadienyloxy, 2,5-dimethyl-1,3-heptadienyloxy, , 4,6-Trimethyl-2,4-heptadienyloxy, 2-octenyloxy, 3-octenyloxy, 4-octenyloxy, 2-methyl-5-octenyloxy, 2-methyl-6 Octenyloxy,
2-methyl-7-octenyloxy, 1,3-octadienyloxy, 1,4-octadienyloxy, 1,5
-Octadienyloxy, 1,6-octadienyloxy, 1,7-octadienyloxy, 2,4-octadienyloxy, 3,7-octadienyloxy, 4,8
-Dimethyl-3,7-octadienyloxy, 2,4,
6-trimethyl-3,7-octadienyloxy, 3,
4-dimethyl-2,5-octadienyloxy, 3,7
-Dimethyl-2,6-octadienyloxy, 4,8-
Dimethyl-2,6-octadienyloxy, 2-nonenyloxy, 3-nonenyloxy, 4-nonenyloxy,
2-methyl-5-nonenyloxy, 2-methyl-6-nonenyloxy, 2-methyl-7-nonenyloxy, 2-
Methyl-8-nonenyloxy, 1,3-nonadienyloxy, 1,4-nonadienyloxy, 1,5-nonadienyloxy, 1,6-nonadienyloxy, 1,7-nonadienyloxy , 1,8-nonadienyloxy, 2,
4-nonadienyloxy, 3,7-nonadienyloxy, 4,8-dimethyl-3,7-nonadienyloxy,
2,4,6-trimethyl-3,7-nonadienyloxy, 3,4-dimethyl-2,5-nonadienyloxy,
4,8-dimethyl-2,6-nonadienyloxy, 2-
Decenyloxy, 3-decenyloxy, 4-decenyloxy, 5-decenyloxy, 2-methyl-6-decenyloxy, 3-methyl-7-decenyloxy, 4-methyl-8-decenyloxy, 5-methyl-9-decenyloxy, 1,3- Decadienyloxy, 1,4-decadienyloxy, 1,5-decadienyloxy, 1,6-decadienyloxy, 1,7-decadienyloxy, 1,8
-Decadienyloxy, 1,9-decadienyloxy,
2-methyl-2,4-decadienyloxy, 3-methyl-2,5-decadienyloxy, 4,8-dimethyl-
2,6-decadienyloxy, 2,4,6-trimethyl-3,7-decadienyloxy, 2,9-dimethyl-
3,7-decadienyloxy, 2-undecenyloxy, 3-undecenyloxy, 4-undecenyloxy, 5-undecenyloxy, 2-methyl-6-undecenyloxy, 3- Methyl-7-undecenyloxy,
4-methyl-8-undecenyloxy, 5-methyl-9
-Undecenyloxy, 2-methyl-10-undecenyloxy, 1,3-undecadienyloxy, 1,4-
Undecadienyloxy, 1,5-undecadienyloxy, 1,6-undecadienyloxy, 1,7-undecadienyloxy, 1,8-undecadienyloxy, 1,9-undecadienyloxy, 1,10-undecadienyloxy, 2-methyl-2,4-undecadienyloxy, 3-methyl-2,5-undecadienyloxy, 4,8-dimethyl-2,6-undecadienyloxy, 2,4,6-trimethyl-3,8-undecadienyloxy, 2,9-dimethyl-3,8-undecadienyloxy, 2-dodecenyloxy, 3-dodecenyloxy, 4-dodecenyloxy, 5-dodecenyloxy, 6- Dodecenyloxy, 2-methyl-7-dodecenyloxy, 3-methyl-8-dodecenyloxy, 4-methyl-9-dodecenyl Carboxymethyl, 5-methyl-10-Dodeseniruokishi, 6-methyl-11-Dodeseniruokishi,
2-methyl-2,4-dodecadienyloxy, 3-methyl-2,5-dodecadienenyloxy, 4,8-dimethyl-2,6-dodecadienenyloxy, 2,4,6-trimethyl-2 , 7-dodecadienyloxy, 2,10-dimethyl-2,8-dodecadienenyloxy, 2,5-dimethyl-3,7-dodecadienenyloxy, 4,8,12-trimethyl-3,7, 11-dodecatrienyloxy,
1,3,5-heptatrienyloxy, 2,4,6-octatrienyloxy, 1,3,6-nonatrienyloxy, 2,6,8-dodecatrienyloxy, 1,5
Examples thereof include alkenyl groups having 1 to 3 straight or branched double bonds having 2 to 12 carbon atoms, such as a 7-undecatrienyloxy group.

Examples of the lower alkanoyloxy group include straight-chain alkanoyloxy groups such as formyloxy, acetyloxy, propionyloxy, butyryloxy, isobutyryloxy, pentanoyloxy, tert-butylcarbonyloxy and hexanoyloxy groups. A chain or branched alkanoyloxy group may be mentioned.

Examples of the lower alkylsulfonyloxy group include those having 1 to 6 carbon atoms such as methylsulfonyloxy, ethylsulfonyloxy, isopropylsulfonyloxy, butylsulfonyloxy, tert-butylsulfonyloxy, pentylsulfonyloxy and hexylsulfonyloxy. A linear or branched alkylsulfonyloxy group can be exemplified.

The lower alkynyloxy group includes, for example, ethynyloxy, 2-propynyloxy, 2-butynyloxy, 3-butynyloxy, 1-methyl-2-propynyloxy, 2-pentynyloxy, 2-hexynyloxy and the like. Examples include 2 to 6 linear or branched alkynyloxy groups.

Examples of the phenyl lower alkoxy group include benzyloxy, 2-phenylethoxy, 1-phenylethoxy, 3-phenylpropoxy, 4-phenylbutoxy, 5-phenylpentyloxy, 6-phenylhexyloxy, 1,1- Examples thereof include a phenylalkoxy group which is a straight-chain or branched-chain alkoxy group having 1 to 6 carbon atoms in the alkoxy moiety such as dimethyl-2-phenylethoxy and 2-methyl-3-phenylpropoxy groups.

Examples of the cycloalkyloxy group include cycloalkyloxy groups having 3 to 8 carbon atoms such as cyclopropyloxy, cyclopentyloxy, cyclohexyloxy, cycloheptyloxy, and cyclooctyloxy groups.

Examples of the cycloalkenyloxy group include cycloalkenyloxy groups having 3 to 8 carbon atoms such as cyclopropenyloxy, cyclobutenyloxy, cyclopentenyloxy, cyclohexenyloxy, cycloheptenyloxy and cyclooctenyloxy. Can be mentioned.

The lower alkanoyl group which may have 1 to 3 halogen atoms as a substituent includes, for example, 2,2,2-trifluoroacetyl and 2,2,2-trichloroacetyl in addition to the lower alkanoyl group. , 2-chloroacetyl, 2-bromoacetyl, 2-fluoroacetyl, 2-iodoacetyl, 2,2-difluoroacetyl, 2,2-dibromoacetyl, 3,3,3-trifluoropropionyl, 3,3,3 -Trichloropropionyl, 3-chloropropionyl, 2,3-dichloropropionyl, 4,4,4-trichlorobutyryl, 4-fluorobutyryl, 5-chloropentanoyl, 3-chloro-2
-Methylpropionyl, 6-bromohexanoyl, 5,
Examples of the substituent such as a 6-dibromohexanoyl group include a linear or branched alkanoyl group having 1 to 6 carbon atoms which may have 1 to 3 halogen atoms.

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

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

Along with the nitrogen atom to which R ⁶ and R ⁷ are attached,
Examples of the 5- or 6-membered saturated or unsaturated heterocyclic ring formed by bonding to each other via or without a nitrogen atom, an oxygen atom or a sulfur atom include pyrrolidinyl, piperidinyl, piperazinyl, morpholino, thiomorpholino, pyrrolyl, and pyrazolyl. , Imidazolyl, imidazolidinyl, pyrrolinyl, imidazolinyl, pyrazolinyl, pyrazolidinyl, oxazolinyl, oxazolidinyl, isoxazolinyl, isoxazolidinyl, thiazolinyl, thiazolidinyl, isothiazolinyl, and isothiazolidinyl groups.

The above heterocycle having a lower alkoxycarbonyl group, a lower alkyl group, a lower alkylthio group or an oxo group as a substituent includes 4-tert-butoxycarbonylpiperazinyl, 4-methylpiperazinyl, 2-ethylthio Imidazolyl, 2-oxopyrrolidinyl, 2-
Oxooxazolidinyl, 3-oxopiperazinyl, 4
-Methoxycarbonylpiperazinyl, 3-ethoxycarbonylpiperidinyl, 2-propoxycarbonylpyrrolidinyl, 3-pentyloxycarbonylthiomorpholino, 2-hexyloxycarbonylthiomorpholino, 3
-Ethoxycarbonylpyrrolyl, 3-methoxycarbonylimidazolyl, 3-ethylpiperidinyl, 3-propylpyrrolidinyl, 3-butylpyrrolyl, 2-pentylimidazolyl, 3-hexylmorpholino, 2-methylthiomorpholino, 2-methyloxazolyl Dinyl, 2-ethylthiazolinyl, 3-methylisoxazolinyl, 2-methylthioimidazolyl, 2-propylthioimidazolinyl, 2-butylthioimidazolidinyl, 3-pentylthiopyrrolyl, 3-hexylthio A straight-chain or branched-chain alkoxycarbonyl having 1 to 6 carbon atoms as a substituent such as pyrrolinyl, 3-methylthiopyrrolidinyl, 3-ethylthiomorpholino, 2-methylthiomorpholino, or 2-methylthioisoxazolidinyl; Group, linear or branched alkyl group having 1 to 6 carbon atoms It can be exemplified the above heterocyclic rings having a straight-chain or branched alkylthio group or an oxo group having 1 to 6 carbon atoms.

A group selected from the group consisting of a halogen atom, a hydroxyl group, a phenyl group and a lower alkoxy group as a substituent is 1
Examples of the lower alkyl group which may have from 1 to 3 include, for example, hydroxymethyl, 2
-Hydroxyethyl, 1-hydroxyethyl, 3-hydroxypropyl, 2,3-dihydroxypropyl, 4-
Hydroxybutyl, 1,1-dimethyl-2-hydroxyethyl, 5,5,4-trihydroxypentyl, 5-hydroxypentyl, 6-hydroxyhexyl, 1-hydroxyisopropyl, 2-methyl-3-hydroxypropyl, trifluoro Methyl, 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, benzyl, 1-phenylethyl, 2-phenylethyl, 3-phenylpropyl, 4-phenylbutyl, 1,1-dimethyl-2-phenylethyl, 5- Phenylpentyl, 6-phenylhexyl, 2-methyl-3
-Phenylpropyl, methoxymethyl, 3-methoxypropyl, 4-ethoxybutyl, 6-propoxyhexyl, 5-isopropoxypentyl, 1,1-dimethyl-
2-butoxyethyl, 2-methyl-3-tert-butoxypropyl, 2-pentyloxyethyl, hexyloxymethyl, dimethoxymethyl, 2,3-dimethoxyethyl, 6,6,5-trimethoxyhexyl, 1-hydroxy- 1-phenylmethyl, 1-hydroxy-2-phenylethyl, 1-hydroxy-3-phenylpropyl, 1
A group selected from the group consisting of a halogen atom, a hydroxyl group, a phenyl group and a linear or branched alkoxy group having 1 to 6 carbon atoms as a substituent such as -methoxy-1-phenylmethyl group;
Examples thereof include a linear or branched alkyl group having 1 to 6 carbon atoms, which may have 1 to 3 carbon atoms.

Examples of the cyano-substituted lower alkoxy group include cyanomethoxy, 2-cyanoethoxy, 1-cyanoethoxy, 3-cyanopropoxy, 4-cyanobutoxy, 5-cyanopentyloxy, 6-cyanohexyloxy, 1,1 Examples thereof include a cyano-substituted alkoxy group which is a linear or branched alkoxy group having 1 to 6 carbon atoms in the alkoxy moiety such as -dimethyl-2-cyanoethoxy and 2-methyl-3-cyanopropoxy groups.

The oxiranyl-substituted lower alkoxy group includes, for example, glycidoxy, 2-oxiranylethoxy,
1-oxiranylethoxy, 3-oxiranylpropoxy, 4-oxiranylbutoxy, 5-oxiranylpentyloxy, 6-oxiranylhexyloxy, 1,1
-Dimethyl-2-oxiranylethoxy, 2-methyl-
An oxiranyl-substituted alkoxy group in which the alkoxy moiety such as a 3-oxiranylpropoxy group is a linear or branched alkoxy group having 1 to 6 carbon atoms can be exemplified.

The phthalimide-substituted alkoxy group includes
For example, phthalimidomethoxy, 2-phthalimidoethoxy, 1-phthalimidoethoxy, 3-phthalimidopropoxy, 4-phthalimidobutoxy, 5-phthalimidopentyloxy, 6-phthalimidohexyloxy,
1,1-dimethyl-2-phthalimidoethoxy, 2-methyl-3-phthalimidopropoxy, 7-phthalimidoheptyloxy, 8-phthalimidooctyloxy, 9
-Phthalimidononyloxy, 10-phthalimidodecyloxy, 11-phthalimidoundecyloxy, 12
A phthalimido-substituted alkoxy group in which the alkoxy moiety such as -phthalimidododecyloxy group is a linear or branched alkoxy group having 1 to 12 carbon atoms.

The pyrrolyl-substituted lower alkoxy group includes
For example, (1-pyrrolyl) methoxy, 2- (2-pyrrolyl) ethoxy, 1- (3-pyrrolyl) ethoxy, 3-
(1-pyrrolyl) propoxy, 4- (1-pyrrolyl) butoxy, 5- (2-pyrrolyl) pentyloxy, 6-
(3-pyrrolyl) hexyloxy, 1,1-dimethyl-
2- (1-pyrrolyl) ethoxy, 2-methyl-3- (1
A pyrrolyl-substituted alkoxy group in which an alkoxy moiety such as-(pyrrolyl) propoxy group is a linear or branched alkoxy group having 1 to 6 carbon atoms can be exemplified.

The amidino-substituted lower alkoxy group includes
For example, amidinomethoxy, 2-amidinoethoxy, 1-
An alkoxy moiety such as amidinoethoxy, 3-amidinopropoxy, 2-amidinobutoxy, 5-amidinopentyloxy, 6-amidinohexyloxy, 1,1-dimethyl-2-amidinoethoxy, or 2-methyl-3-amidinopropoxy is An amidino-substituted alkoxy group which is a straight-chain or branched-chain alkoxy group having 1 to 6 carbon atoms can be exemplified.

Examples of the lower alkanoyloxy lower alkyl group include acetyloxymethyl, 2-propionyloxyethyl, 1-butyryloxyethyl, 3-acetyloxypropyl, 4-isobutyryloxybutyl,
A straight-chain having 2 to 6 carbon atoms such as 5-pentanoyloxypentyl, 6-tert-butylcarbonyloxyhexyl, 1,1-dimethyl-2-hexanoyloxyethyl, and 2-methyl-3-acetyloxypropyl; A branched-chain alkanoyloxy group may be a straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms.

Examples of the lower alkylsulfinyl group include straight-chain or branched alkyl having 1 to 6 carbon atoms such as methylsulfinyl, ethylsulfinyl, isopropylsulfinyl, butylsulfinyl, tert-butylsulfinyl, pentylsulfinyl and hexylsulfinyl. An example is a sulfinyl group.

Examples of the lower alkenyl group which may have a hydroxyl group as a substituent include 1-hydroxyallyl, 4-hydroxy-1-butenyl, 4-hydroxy-2-butenyl and 2-hydroxyl, in addition to the above-mentioned lower alkenyl groups. -3-butenyl, 5-hydroxy-2-pentenyl, 6
Examples of the substituent such as -hydroxy-2-hexenyl group include a straight or branched alkenyl group having 2 to 6 carbon atoms which may have a hydroxyl group.

Examples of the lower alkylenedioxy group include those having 1 to 4 carbon atoms such as methylenedioxy, ethylenedioxy, trimethylenedioxy and tetramethylenedioxy groups.
And a straight-chain or branched alkylenedioxy group.

Examples of the lower alkylsilyl group include those having 1 to 1 carbon atoms such as methylsilyl, ethylsilyl, propylsilyl, isopropylsilyl, butylsilyl, tert-butylsilyl, pentylsilyl, hexylsilyl, dimethylsilyl, trimethylsilyl and dimethyl-tert-butylsilyl. A silyl group having 1 to 3 linear or branched alkyl groups of 6 can be exemplified.

Examples of the amino group which may have a lower alkanoyl group include amino, formylamino, acetylamino, propionylamino, butyrylamino, isobutyrylamino, pentanoylamino, tert-butylcarbonylamino, hexanoylamino and the like. Carbon number 1
Examples of the amino group which may have from 6 to 6 linear or branched alkanoyl groups can be given.

A group selected from the group consisting of an amino group and a nitro group which may have one or two groups selected from the group consisting of a lower alkanoyl group, a lower alkyl group and a benzoyl group as a substituent on the phenyl ring is represented by the following formula: Examples of the phenoxycarbonyl group which may have up to 3 include phenoxycarbonyl, 2-nitrophenoxycarbonyl, 3-nitrophenoxycarbonyl, 4-nitrophenoxycarbonyl, 3,4-dinitrophenoxycarbonyl, 2,5-
Dinitrophenoxycarbonyl, 2,6-dinitrophenoxycarbonyl, 3,4,5-trinitrophenoxycarbonyl, 2-aminophenoxycarbonyl, 3-aminophenoxycarbonyl, 4-aminophenoxycarbonyl, 3-acetylaminophenoxycarbonyl,
-Formylaminophenoxycarbonyl, 4-isobutyrylaminophenoxycarbonyl, 2-pentanoylaminophenoxycarbonyl, 3-hexanoylaminophenoxycarbonyl, 3,4-diacetylaminophenoxycarbonyl, 3,4-diaminophenoxycarbonyl, 2, 6-diaminophenoxycarbonyl, 2,5-
Diaminophenoxycarbonyl, 2,4,6-triaminophenoxycarbonyl, 4-acetylaminophenoxycarbonyl, 4-dimethylaminophenoxycarbonyl, 4-benzoylaminophenoxycarbonyl, 3-
A straight or branched chain having 1 to 6 carbon atoms as a substituent on a phenyl ring such as (N-methyl-N-benzoylamino) phenoxycarbonyl, 2- (N-ethyl-N-acetylamino) phenoxycarbonyl, etc. An alkanoyl group, a linear or branched alkyl group having 1 to 6 carbon atoms, a group selected from the group consisting of amino group and nitro group which may have 1 to 2 groups selected from the group consisting of benzoyl group; Phenoxycarbonyl groups which may have 1 to 3 groups can be exemplified.

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

Examples of the amino group which may have a lower alkoxycarbonyl group include amino, methoxycarbonylamino, ethoxycarbonylamino, propoxycarbonylamino, isopropoxycarbonylamino,
Examples thereof include amino groups which may have a linear or branched alkoxycarbonyl group having 1 to 6 carbon atoms, such as butoxycarbonylamino, tert-butoxycarbonylamino, pentyloxycarbonylamino, and hexyloxycarbonylamino groups.

The lower alkanoyl group which may have an amino group which may have a lower alkoxycarbonyl group as a substituent on the lower alkanoyl group includes phenylacetyl, 3-phenylpropionyl,
-Phenylpropionyl, 4-phenylbutyryl, 2,
2-dimethyl-3-phenylpropionyl, 5-phenylpentanoyl, 6-phenylhexanoyl, 3-methyl-4-phenylbutyryl, 2-amino-4-phenylacetyl, 2-tert-butoxycarbonylamino-2-
Phenylacetyl, 2-methoxycarbonylamino-2
-Phenylacetyl, 2-ethoxycarbonylamino-
Substitution on alkanoyl groups such as 3-phenylpropionyl, 2-propoxycarbonylamino-4-phenylbutyryl, 2-pentyloxycarbonylamino-5-phenylpentanoyl, 2-hexyloxycarbonylamino-6-phenylhexanoyl A group having 1 to 6 carbon atoms
A phenylalkanoyl group which is a linear or branched alkanoyl group having 2 to 6 carbon atoms in an alkanoyl group part which may have an amino group which may have a linear or branched alkoxycarbonyl group it can.

Examples of the alkanoyl group include, in addition to the lower alkanoyl group, a linear or branched alkanoyl group having 1 to 12 carbon atoms such as heptyl, octanoyl, nonanoyl, decanoyl, undecanoyl, dodecanoyl, neopentanoyl and the like. Can be illustrated.

The alkenylcarbonyl group includes, for example, vinylcarbonyl, acrylcarbonyl, 3-methyl-
2-butenylcarbonyl, 2-butenylcarbonyl, 1
-Methylallylcarbonyl, 2-pentenylcarbonyl, 2-hexenylcarbonyl, 1-heptenylcarbonyl, 1-octenylcarbonyl, 1-nonenylcarbonyl, 1-decenylcarbonyl, 1-undecenylcarbonyl, 1-do Decenylcarbonyl, 1-heptenylcarbonyl, 3-heptenylcarbonyl, 2-methyl-4
-Heptenylcarbonyl, 2-methyl-5-heptenylcarbonyl, 4-methyl-2-heptenylcarbonyl,
3-methyl-1-heptenylcarbonyl, 1,3-heptadienylcarbonyl, 1,4-heptadienylcarbonyl, 1,5-heptadienylcarbonyl, 1,6-heptadienylcarbonyl, 2,4- Heptadienylcarbonyl, 2-methyl-2,4-heptadienylcarbonyl, 2,6-dimethyl-2,4-heptadienylcarbonyl, 2,6-dimethyl-1,5-heptadienylcarbonyl, 2, 5-dimethyl-1,3-heptadienylcarbonyl, 2,4,6-trimethyl-2,4-heptadienylcarbonyl, 2-octenylcarbonyl, 3-octenylcarbonyl, 4-octenylcarbonyl, 2-
Methyl-5-octenylcarbonyl, 2-methyl-6
Octenylcarbonyl, 2-methyl-7-octenylcarbonyl, 1,3-octadienylcarbonyl, 1,4
-Octadienylcarbonyl, 1,5-octadienylcarbonyl, 1,6-octadienylcarbonyl, 1,
7-octadienylcarbonyl, 2,4-octadienylcarbonyl, 3,7-octadienylcarbonyl,
4,8-dimethyl-3,7-octadienylcarbonyl, 2,4,6-trimethyl-3,7-octadienylcarbonyl, 3,4-dimethyl-2,5-octadienylcarbonyl, 4,8 -Dimethyl-2,6-octadienylcarbonyl, 2-nonenylcarbonyl, 3-nonenylcarbonyl, 4-nonenylcarbonyl, 2-methyl-
5-nonenylcarbonyl, 2-methyl-6-nonenylcarbonyl, 2-methyl-7-nonenylcarbonyl, 2-
Methyl-8-nonenylcarbonyl, 1,3-nonadienylcarbonyl, 1,4-nonadienylcarbonyl, 1,
5-nonadienylcarbonyl, 1,6-nonadienylcarbonyl, 1,7-nonadienylcarbonyl, 1,8-
Nonadienylcarbonyl, 2,4-nonadienylcarbonyl, 3,7-nonadienylcarbonyl, 4,8-dimethyl-3,7-nonadienylcarbonyl, 2,4,6-
Trimethyl-3,7-nonadienylcarbonyl, 3,4
-Dimethyl-2,5-nonadienylcarbonyl, 4,8
-Dimethyl-2,6-nonadienylcarbonyl, 2-decenylcarbonyl, 3-decenylcarbonyl, 4-decenylcarbonyl, 5-decenylcarbonyl, 2-methyl-6-decenylcarbonyl , 3-methyl-7-decenylcarbonyl, 4-methyl-8-decenylcarbonyl, 5
-Methyl-9-decenylcarbonyl, 1,3-decadienylcarbonyl, 1,4-decadienylcarbonyl,
1,5-decadienylcarbonyl, 1,6-decadienylcarbonyl, 1,7-decadienylcarbonyl, 1,
8-decadienylcarbonyl, 1,9-decadienylcarbonyl, 2-methyl-2,4-decadienylcarbonyl, 3-methyl-2,5-decadienylcarbonyl,
4,8-dimethyl-2,6-decadienylcarbonyl,
2,4,6-trimethyl-3,7-decadienylcarbonyl, 2,9-dimethyl-3,7-decadienylcarbonyl, 2-undecenylcarbonyl, 3-undecenylcarbonyl, 4-undecenyl Carbonyl, 5-undecenylcarbonyl, 2-methyl-6-undecenylcarbonyl, 3-methyl-7-undecenylcarbonyl,
-Methyl-8-undecenylcarbonyl, 5-methyl-
9-undecenylcarbonyl, 2-methyl-10-undecenylcarbonyl, 1,3-undecadienylcarbonyl, 1,4-undecadienylcarbonyl, 1,5-
Undecadienylcarbonyl, 1,6-undecadienylcarbonyl, 1,7-undecadienylcarbonyl,
1,8-undecadienylcarbonyl, 1,9-undecadienylcarbonyl, 1,10-undecadienylcarbonyl, 2-methyl-2,4-undecadienylcarbonyl, 3-methyl-2,5-undecadi Enylcarbonyl, 4,8-dimethyl-2,6-undecadienylcarbonyl, 2,4,6-trimethyl-3,8-undecadienylcarbonyl, 2,9-dimethyl-3,8-undecadienylcarbonyl, 2-dodecenylcarbonyl,
3-dodecenylcarbonyl, 4-dodecenylcarbonyl, 5-dodecenylcarbonyl, 6-dodecenylcarbonyl, 2-methyl-7-dodecenylcarbonyl, 3-methyl-8- Dodecenylcarbonyl, 4-methyl-9-dodecenylcarbonyl, 5-methyl-10-dodecenylcarbonyl, 6-methyl-11-dodecenylcarbonyl,
2-methyl-2,4-dodecadienylcarbonyl, 3-
Methyl-2,5-dodecadienylcarbonyl, 4,8-
Dimethyl-2,6-dodecadienylcarbonyl, 2,
4,6-trimethyl-2,7-dodecadienylcarbonyl, 2,10-dimethyl-2,8-dodecadienenylcarbonyl, 2,5-dimethyl-3,7-dodecadienenylcarbonyl, 4,8,12 -Trimethyl-3,7,11-
Dodecatrienylcarbonyl, 1,3,5-heptatrienylcarbonyl, 2,4,6-octatrienylcarbonyl, 1,3,6-nonatrienylcarbonyl, 2,
Examples thereof include alkenylcarbonyl groups having 1 to 3 straight or branched double bonds having 2 to 12 carbon atoms, such as 6,8-dodecatrienylcarbonyl and 1,5,7-undecatrienylcarbonyl groups. .

The phenylsulfonyl group which may have a lower alkoxy group as a substituent on the phenyl ring includes, for example, phenylsulfonyl, 2-methoxyphenylsulfonyl, 3-methoxyphenylsulfonyl, 4-methoxyphenylsulfonyl, 2-ethoxyphenyl Sulfonyl, 3-ethoxyphenylsulfonyl, 4-ethoxyphenylsulfonyl, 4-isopropoxyphenylsulfonyl, 4-pentyloxyphenylsulfonyl,
-Hexyloxyphenylsulfonyl, 3,4-dimethoxyphenylsulfonyl, 3-ethoxy-4-methoxyphenylsulfonyl, 2,3-dimethoxyphenylsulfonyl, 3,4-diethoxyphenylsulfonyl, 2,
Substituents on the phenyl ring such as 5-dimethoxyphenylsulfonyl, 2,6-dimethoxyphenylsulfonyl, 3,5-dimethoxyphenylsulfonyl, 3,4-dipentyloxyphenylsulfonyl, and 3,4,5-trimethoxyphenylsulfonyl groups Examples thereof include a phenylsulfonyl group which may have 1 to 3 straight or branched alkoxy groups having 1 to 6 carbon atoms.

An amino group which may have, on the phenyl ring, a lower alkoxy group, a lower alkyl group, a halogen atom, and one or two groups selected from a lower alkyl group and a lower alkanoyl group as a substituent; Examples of the phenyl group which may have 1 to 3 groups selected from the group consisting of nitro groups include phenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl,
-Ethoxyphenyl, 3-ethoxyphenyl, 4-ethoxyphenyl, 4-isopropoxyphenyl, 3-butoxyphenyl, 4-pentyloxyphenyl, 4-hexyloxyphenyl, 3,4-dimethoxyphenyl,
-Ethoxy-4-methoxyphenyl, 2,3-dimethoxyphenyl, 3,4-diethoxyphenyl, 2,4-diethoxyphenyl, 2,5-dimethoxyphenyl, 2,
6-dimethoxyphenyl, 3,5-dimethoxyphenyl, 3,4-dipentyloxyphenyl, 3,4,5-
Trimethoxyphenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 4-isopropylphenyl, 3-butylphenyl, 4-pentylphenyl, -Hexylphenyl, 3,4-dimethylphenyl, 3,4-diethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4,5-
Trimethylphenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2
-Bromophenyl, 3-bromophenyl, 4-bromophenyl, 2-iodophenyl, 3-iodophenyl,
-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-nitrophenyl, 3-nitrophenyl, 4-nitrophenyl, 3,
4-dinitrophenyl, 2,5-dinitrophenyl,
2,6-dinitrophenyl, 3,4,5-trinitrophenyl, 2-aminophenyl, 3-aminophenyl,
-Aminophenyl, 3- (N-acetylamino) phenyl, 4- (N-formylamino) phenyl, 4- (N-
Isobutyrylamino) phenyl, 2- (N-pentanoylamino) phenyl, 3,4-diaminophenyl, 3,
4-di (N-acetylamino) phenyl, 3,4,5-
Triaminophenyl, 2,6-diaminophenyl, 2,
5-diaminophenyl, 3,5-di-t-butyl-4-
Hydroxyphenyl, 3-hydroxy-4-pentyloxyphenyl, 2-hydroxy-5-t-butylphenyl, 3,5-dichloro-4-aminophenyl, 3-amino-4-hydroxyphenyl, 3-acetylamino-4
-Methoxyphenyl, 3-nitro-4-acetylaminophenyl, 3-nitro-4-chlorophenyl, 3-chloro-4-methylphenyl, 3-methoxy-4-methyl-
5-iodophenyl, 3,4-dimethoxy-5-bromophenyl, 3,5-diiodo-4-methoxyphenyl,
4-dimethylaminophenyl, 3-methylaminophenyl, 2-butylaminophenyl, 4-diethylaminophenyl, 3-dipropylaminophenyl, 2- (N-methyl-N-hexylamino) phenyl, 4- (N-methyl -N-acetylamino) phenyl, a linear or branched alkoxy group having 1 to 6 carbon atoms as a substituent on a phenyl ring such as a 2,4-dimethylaminophenyl group,
A straight-chain or branched-chain alkyl group having 6 carbon atoms, a halogen atom, a straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms and a straight-chain or branched-chain alkanoyl group having 1 to 6 carbon atoms as substituents. Examples include an amino group which may have 1 to 2 groups selected from the group and a phenyl group which may have 1 to 3 groups selected from the group consisting of the nitro group.

As the heterocyclic carbonyl group, for example, 2-
Pyrrolidinylcarbonyl, 3-pyrrolidinylcarbonyl, 1-piperidinylcarbonyl, 1-piperazinylcarbonyl, morpholinocarbonyl, thiomorpholinocarbonyl, 2-tetrahydrofurylcarbonyl, 2-thienylcarbonyl, 3-thienylcarbonyl, 2-thienylcarbonyl, -Pyrrolylcarbonyl, 3-pyrrolylcarbonyl, 2-furoyl, 3-furoyl, 2-pyridylcarbonyl, 3-pyridylcarbonyl, 4-pyridinylcarbonyl, 3-pyridazylcarbonyl, 2-thiazolylcarbonyl, 2-oxazolylcarbonyl, 2-imidazolylcarbonyl,
4-pyridylcarbonyl, 5-pyridylcarbonyl, 6-pyridylcarbonyl, 2-pyrimidylcarbonyl, 4-pyrimidylcarbonyl, 5-pyrimidylcarbonyl, 6-pyrimidylcarbonyl, 2 -Pyrazylcarbonyl, 3-pyrazylcarbonyl, 6-quinolylcarbonyl, 5-indolylcarbonyl, 6-isoquinolylcarbonyl, 4-cinnolylcarbonyl, 3-quinoxalylcarbonyl, 4-phthalazylcarbonyl, 5 Nitrogen atoms such as -quinazolylcarbonyl, 3-benzo [b] furanylcarbonyl, 5-benzo [b] thiophenylcarbonyl, 2-oxo-6-quinolylcarbonyl, and 2-oxo-4-quinolylcarbonyl groups A 5- to 10-membered monocyclic or binomial heterocyclic carbonyl group having 1 or 2 oxygen atoms and / or sulfur atoms It can be exemplified.

The heterocyclic group having 1 to 3 groups selected from the group consisting of a phenyl lower alkoxycarbonyl group, a phenyl lower alkoxy group, an oxo group, a lower alkyl group and a lower alkylenedioxy group as the substituent is 1 −
Benzyloxycarbonyl-2-pyrrolidinylcarbonyl, 3-benzyloxycarbonyl-4,5- (1,1
-Dimethylmethylene) -2-tetrahydrofurylcarbonyl, 4- (2-phenylethoxycarbonyl) -1-
Piperazinylcarbonyl, 3-methyl-2-thienylcarbonyl, 3-ethyl-2-pyrrolylcarbonyl, 3-
Propyl-2-furoyl, 4-butyl-2-oxo-6
-Quinolylcarbonyl, 6-pentyl-2-oxo-4
-Quinolylcarbonyl, 5-hexyl-2-pyrazylcarbonyl, 1,3-dioxo-2-methyl-6-quinazolyl, 4,5-methylenedioxy-3-indolylcarbonyl, 3- (3-phenylpropoxy ) A phenylalkoxycarbonyl group in which the alkoxycarbonyl moiety is a linear or branched alkoxycarboxy group having 1 to 6 carbon atoms as a substituent such as a morpholinocarbonyl group, and a linear or branched alkoxy moiety having 1 to 6 carbon atoms A phenylalkoxy group that is a chain alkoxy group, an oxo group,
The above-mentioned heterocyclic group having 1 to 3 groups selected from the group consisting of a straight-chain or branched-chain alkyl group of 6 and a straight-chain or branched-chain alkylenedioxy group having 1 to 4 carbon atoms can be exemplified.

The thienyl lower alkanoyl group includes 2
-(2-thienyl) acetyl, 3- (3-thienyl) propionyl, 2- (3-thienyl) propionyl, 4-
(2-thienyl) butyryl, 2,2-dimethyl-3-
(3-thienyl) propionyl, 5- (2-thienyl)
Pentanoyl, 6- (3-thienyl) hexanoyl, 3
An example is a thienylalkanoyl group in which the alkanoyl group portion such as -methyl-4- (2-thienyl) butyryl group is a straight or branched alkanoyl group having 2 to 6 carbon atoms.

The tricyclo [3.3.1.1] decanyl lower alkanoyl group includes, for example, 2-tricyclo [3.3.1.1] decanylacetyl, 3-tricyclo [3.3.1. 1] decanylpropionyl, 2-tricyclo [3.3.1.1] decanylpropionyl, 4
Tricyclo [3.3.1.1] decanylbutyryl,
2,2-dimethyl-3-tricyclo [3.3.1.
1] decanylpropionyl, 5-tricyclo [3.
3.1.1] decanyl pentanoyl, 6-tricyclo [3.3.1.1] decanyl hexanoyl, 3-methyl-4-tricyclo [3.3.1.1] decanyl butyryl group, etc. A tricyclo wherein the alkanoyl group part is a linear or branched alkanoyl group having 2 to 6 carbon atoms [3.3.
1.1] A decanylalkanoyl group can be exemplified.

The benzoyl group which may have a lower alkoxy group on the phenyl ring includes, for example, benzoyl,
2-methoxybenzoyl, 3-methoxybenzoyl, 4
-Methoxybenzoyl, 2-ethoxybenzoyl, 3-
Ethoxybenzoyl, 4-butoxybenzoyl, 4-isopropoxybenzoyl, 4-pentyloxybenzoyl, 4-hexyloxybenzoyl, 3,4-dimethoxybenzoyl, 3-ethoxy-4-methoxybenzoyl, 2,3-dimethoxybenzoyl, , 4-Diethoxybenzoyl, 2,5-dimethoxybenzoyl, 2,6
Phenyl rings such as dimethoxybenzoyl, 2,4-dimethoxybenzoyl, 2,4,6-trimethoxybenzoyl, 3,5-dimethoxybenzoyl, 3,4-dipentyloxybenzoyl, and 3,4,5-trimethoxybenzoyl groups A benzoyl group which may have 1 to 3 straight or branched alkoxy groups having 1 to 6 carbon atoms thereon can be exemplified.

The phenyl group which may have a lower alkoxy group on the phenyl ring includes, for example, phenyl, 2-phenyl
Methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2-ethoxyphenyl, 3-ethoxyphenyl, 4-ethoxyphenyl, 4-isopropoxyphenyl, 3-butoxyphenyl, 4-pentyloxyphenyl, 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- A phenyl group which may have 1 to 3 carbon atoms of a linear or branched alkoxy group having 1 to 6 carbon atoms on a phenyl ring such as a trimethoxyphenyl group can be exemplified.

Examples of the cycloalkyl group include those having 3 carbon atoms such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl.
To 8 cycloalkyl groups.

The saturated or unsaturated heterocyclic ring formed by bonding to each other via a nitrogen atom, an oxygen atom or a sulfur atom together with or without a nitrogen atom to which R ¹¹ and R ¹² are bonded is, for example, pyrrolidinyl, piperidinyl, Piperazinyl, morpholino, thiomorpholino, pyrrolyl, imidazolyl, pyrazolyl, imidazolidinyl, pyrazolinyl, pyrazolidinyl, oxazolinyl, oxazolidinyl, isoxazolinyl, isoxazolidinyl, thiazolinyl, thiazolidinyl, isothiazolinyl, isothiazolinyl, 1,2 , 4-tetrahydroquinolyl, 1,2-dihydroquinolyl, indolyl, isoindolyl, 1,2-dihydroisoquinolyl, 1,2,3
4-tetrahydroisoquinolyl, 1H-indazolyl,
1,2-dihydroquinazolyl, 1,2-dihydrocinnolyl, 1,2-dihydroquinoxalyl, 1,2,3,4
A 5- or 10-membered saturated or unsaturated monocyclic or binomilic ring such as -tetrahydroquinazolyl, 1,2,3,4-tetrahydrocinnolyl, 1,2,3,4-tetrahydroquinoxalyl group Can be exemplified.

The phenyl group which may have a substituent selected from the group consisting of a lower alkoxy group and a lower alkanoyl group on the phenyl ring includes, for example, phenyl,
2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2-ethoxyphenyl, 3-ethoxyphenyl, 4-ethoxyphenyl, 4-isopropoxyphenyl, 3-butoxyphenyl, 4-pentyloxyphenyl, 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, 3-methoxy-4-acetylphenyl, 2
-Acetylphenyl, 3-acetylphenyl, 4-acetylphenyl, 2-formylphenyl, 3-propionylphenyl, 4-isobutyrylphenyl, 2-pentanoylphenyl, 3-hexanoylphenyl, 3,4-diacetylphenyl, 2,5-diacetylphenyl, 3,
A linear or branched alkoxy group having 1 to 6 carbon atoms and a linear or branched alkanoyl group having 1 to 6 carbon atoms as substituents on a phenyl ring such as a 4,5-triacetylphenyl group; A phenyl group which may have 1 to 3 groups selected more can be exemplified.

A benzoyl group, a lower alkanoyl group, a phenyl lower alkyl group, and a phenyl group which may have a substituent selected from the group consisting of a lower alkoxy group and a lower alkanoyl group on the phenyl ring; Examples of the above heterocyclic ring having a group selected from 3-benzoyl-1-pyrrolidinyl, 4-benzoyl-
1-piperidinyl, 4-benzoyl-1-piperazinyl, 4-benzyl-1-piperazinyl, 3- (2-phenylethyl) morpholino, 3- (3-phenylpropyl) thiomorpholino, 3- (4-phenylbutyl)- 1
-Pyrrolyl, 4-acetyl-1-piperidinyl, 4-acetyl-1-piperazinyl, 4-formyl-1-piperazinyl, 2- (5-phenylpentyl) -1-imidazolyl, 3- (6-phenylpentyl) -1 -Pyrazolyl, 4- (4-methoxyphenyl) -1-piperazinyl, 4- (4-acetylphenyl) -1-piperazinyl, 4- (3-ethoxyphenyl) -1-piperazinyl, 4- (3-propionylphenyl) -1-piperazinyl, 5-benzyl-1,2,3,4-tetrahydroquinolin-1-yl, 6- (4-butyrylphenyl)-
1,2,3,4-tetrahydroisoquinolin-2-yl, 4- (2-propoxyphenyl) -1-indolyl, 5- (3-pentanoylphenyl) -1H-indazol-1-yl, 6- (3 -Butoxyphenyl)-
1,2-dihydroquinazolin-1-yl, 7- (4-hexanoylphenyl) -1,2-dihydrocinnoline-
2-yl, 6- (4-hexyloxyphenyl) -1,
A benzoyl group as a substituent such as a 2,3,4-tetrahydroquinoxalin-1-yl group or the like, wherein the alkyl moiety has 1 carbon atom
A straight-chain or branched-chain alkoxy group having 1 to 6 carbon atoms and a straight-chain or branched-chain alkoxy group having 1 to 6 carbon atoms, A group selected from the group consisting of branched alkanoyl groups
Examples of the above heterocyclic ring having a group selected from the group of phenyl groups which may have from 3 to 3 can be given.

Examples of the alkylene group include, in addition to the lower alkylene group, heptamethylene, octamethylene, nonamethylene, decamethylene, undecamethylene,
Examples thereof include a linear or branched alkylene group having 1 to 12 carbon atoms such as a dodecamethylene group.

The lower alkyl group which may have an amino group which may have a phenyl lower alkoxycarbonyl group as a hydroxyl group or a substituent on the lower alkyl group may be, for example, -Hydroxy-1-methoxycarbonylmethyl, 1-methoxycarbonyl-2-hydroxyethyl, 3-hydroxy-3-methoxycarbonylpropyl, 2-hydroxy-4-ethoxycarbonylbutyl, 2-hydroxy-6-propoxycarbonylhexyl, 2 -Hydroxy-2-pentyloxycarbonylethyl, 1-hydroxy-1-hexyloxycarbonylmethyl, 5-benzyloxycarbonylamino-
On an alkyl group such as 1-methoxycarbonylpentyl, 5-amino-1-methoxycarbonylpentyl, 3- (2-phenylethoxycarbonylamino) -1-ethoxycarbonylpropyl, 4-amino-1-butyloxycarbonylbutyl, etc. An alkyl moiety which may have an amino group which may have a phenylalkoxycarbonyl group in which an alkoxycarbonyl group part is a straight-chain or branched alkoxycarbonyl group having 1 to 6 carbon atoms as a hydroxyl group or a substituent has 1 carbon atom And straight-chain or branched-chain alkoxycarbonylalkyl groups having 1 to 6 carbon atoms, which are straight-chain or branched-chain alkyl groups having 1 to 6 carbon atoms.

The lower alkanoyl group may have a phenyl lower alkoxycarbonylamino group as a substituent, a hydroxyl group, a phenyl group which may have a hydroxyl group as a substituent on the phenyl ring, a carbamoyl group, an imidazolyl group or a lower alkylthio group. Or, as a substituent on an amino group, a lower alkyl group which may have a hydroxyl group as a substituent, a lower alkenyl group, a phenyl lower alkyl group which may have a lower alkoxy group as a substituent on a phenyl ring, a lower alkylsulfonyl group Examples of the amino lower alkanoyl group which may have a lower alkanoyl group or a phenyl lower alkoxycarbonyl group include, for example, aminoacetyl, 3-formylaminopropionyl,
Acetylaminoacetyl, 2-propionylaminopropionyl, 4-butyrylaminobutyryl, 2,2-dimethyl-3-isobutyrylaminopropionyl, 5-pentanoylaminopentanoyl, 6-tert-butylcarbonylaminohexanoyl, 3-methyl-4-hexanoylaminobutyryl, 4-methylthio-2-acetylaminobutyryl, 3- (imidazol-4-yl) -2-acetylaminopropionyl, 2-acetylaminopropionyl, 3- (4- (Hydroxyphenyl) -2-benzyloxycarbonylaminopropionyl, 4-carbamoyl-2-acetylaminobutyryl, 2-acetylaminoisopentanoyl, 5-ethylthio-2-acetylaminopentanoyl, 4- (imidazol-2-yl )-
2-propionylaminobutyryl, 6- (2-hydroxyphenyl) -2-butyrylaminohexanoyl, 3-
Carbamoyl-2-benzyloxycarbonylaminopropionyl, 5-carbamoyl-2- (2-phenylethoxycarbonylamino) pentanoyl, 3- (2,4
-Dihydroxyphenyl) -2- (3-phenylpropoxycarbonylamino) propionyl, 2,5-dibenzyloxycarbonylaminohexanoyl, 3- (4-
(Hydroxyphenyl) -2-aminopropionyl, dimethylaminoacetyl, 3-hydroxy-2-benzyloxycarbonylaminopropionyl, 2-benzyloxycarbonylaminopropionyl, 2-aminopropionyl, 2-aminoisopentanoyl, 2-aminobutyryl, -Benzyloxycarbonylaminobutyryl, diethylaminoacetyl, 4-acetylaminobutyryl,
4-dimethylaminobutyryl, 2-hydroxyacetyl, ethylaminoacetyl, allylaminoacetyl, benzylaminoacetyl, isopropylaminoacetyl,
(N-methyl-N-benzylamino) acetyl, [N-
Methyl-N- (2-hydroxyethyl) amino] acetyl, [N-methyl-N- (4-ethoxybenzyl) amino] acetyl, 2-benzyloxycarbonylaminoacetyl, methylsulfonylaminoacetyl, (3-methoxybenzyl) Aminoacetyl, (N-methyl-N-acetylamino) acetyl, 5- (N-methyl-N-allylamino) pentanoyl, 6- [N-allyl-N-
(3,4-dimethoxybenzyl) amino] phenylalkoxycarbonylamino which is a straight-chain or branched-chain alkoxycarbonyl group having 1 to 6 carbon atoms in the lower alkoxycarbonyl group as a substituent on an alkanoyl group such as a hexanoyl group May have a phenyl group, a carbamoyl group, an imidazolyl group, or a linear or branched alkylthio group having 1 to 6 carbon atoms, which may have 1 to 3 hydroxyl groups as substituents on the phenyl ring. Or a straight-chain or branched alkyl group having 1 to 6 carbon atoms, which may have 1 to 3 hydroxyl groups as a substituent on the amino group, a straight-chain or branched alkyl group having 2 to 6 carbon atoms The alkenyl group may have 1 to 3 straight or branched chain alkoxy groups having 1 to 6 carbon atoms as a substituent on the phenyl ring, and the alkyl moiety may have 1 to 3 carbon atoms. A phenylalkyl group which is a straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms, a straight-chain or branched-chain alkylsulfonyl group having 1 to 6 carbon atoms, a straight-chain or branched-chain alkanoyl group having 1 to 6 carbon atoms Or a linear or branched alkanoyl having 2 to 6 carbon atoms having an amino group which may have a phenylalkoxycarbonyl group wherein the alkoxycarbonyl moiety is a linear or branched alkoxycarbonyl group having 1 to 6 carbon atoms Groups can be exemplified.

A lower alkyl group may have a phenyl group, an imidazolyl group, a carbamoyl group or a lower alkylthio group which may have a hydroxyl group as a substituent on a phenyl ring as a substituent, and a substituent on an amide group as a substituent. Amides that may have a lower alkyl group include, for example, carbamoylmethyl, 2-carbamoylethyl, 1-carbamoylethyl, 3-carbamoylpropyl, 4-carbamoylbutyl, 5-carbamoylpentyl, 6-carbamoylhexyl, 1-dimethyl-2-carbamoylethyl, 2-methyl-3-carbamoylpropyl, methylamidomethyl, 1-ethylamidoethyl, 2-propylamidoethyl, 3-isopropylamidopropyl, 4-butylamidobutyl, 5-
Pentylamidopentyl, 6-hexylamidohexyl, dimethylamidomethyl, (N-ethyl-N-propylamido) methyl, 2- (N-methyl-N-hexylamido) ethyl, 2- (4-hydroxyphenyl) -carbamoyl Ethyl, 1-carbamoylisobutyl, 2-
(Imidazol-4-yl) -1-carbamoylethyl, 1,3-dicarbamoylpropyl, 3-methylthio-1-carbamoylpropyl, 3- (2-hydroxyphenyl) -1-methylamidopropyl, 4- (2 6-
Dihydroxyphenyl) -1- (N-methyl-N-hexylamido) butyl, 3- (imidazol-2-yl)
-1-propylamidopropyl, 1,4-dicarbamoylbutyl, 2-ethylthio-1-butylamidobutyl,
A phenyl group, an imidazolyl group, a carbamoyl group or a carbon number of 1 to 6 which may have 1 to 3 hydroxyl groups as a substituent on a phenyl ring as a substituent on an alkyl group such as a 4-pentylthio-1-hexylamidobutyl group; An amide group which may have a linear or branched alkylthio group having 1 to 6 carbon atoms as a substituent or a linear or branched alkyl group having 1 to 6 carbon atoms on the amide group. And a straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms.

Examples of the carboxy lower alkyl group include carboxymethyl, 2-carboxyethyl, 1-carboxyethyl, 3-carboxypropyl, 4-carboxybutyl, 5-carboxypentyl, 6-carboxyhexyl, and 1,1-dimethyl- 2-carboxyethyl, 2
Examples thereof include a carboxyalkyl group in which the alkyl portion such as a -methyl-3-carboxypropyl group is a linear or branched alkyl group having 1 to 6 carbon atoms.

As the lower alkoxy lower alkyl group,
For example, methoxymethyl, 2-ethoxymethyl, 1-methoxymethyl, 3-methoxypropyl, 4-ethoxybutyl, 6-propoxyhexyl, 5-isopropoxypentyl, 1,1-dimethyl-2-butoxyethyl, 2-methyl- Alkyl moiety such as 3-tert-butoxypropyl, 2-pentyloxyethyl, hexyloxymethyl group is a linear or branched C1-C6 alkyl group having 1-6 carbon atoms. A chain alkoxyalkyl group can be exemplified.

The amino acid residue capable of forming an amide bond with the amino group to which R ⁴ or R ⁵ binds includes, for example, alanine residue, N ² -arginine residue, N ⁵ -arginine residue, N ⁶ -arginine residue. A group, an N ⁴ -asparagine residue,
Aspartic acid, N ⁵ - glutamine residue, cysteine residue, glutamic acid residue, glycine residue, histidine residue, isoleucine residue, leucine residue, N ² - lysine residues, N ⁶ - lysine residues, Examples thereof include a methionine residue, a phenylalanine residue, a proline residue, a serine residue, a threonine residue, a tryptophan residue, a tylosin residue, and a valine residue.

Examples of the hydroxyimino lower alkyl group include hydroxyiminomethyl, 1-hydroxyiminoethyl, 2-hydroxyiminoethyl, 3-hydroxyiminopropyl, 4-hydroxyiminobutyl,
Straight chain or branched chain having 1 to 6 carbon atoms in the alkyl moiety such as -hydroxyiminopentyl, 6-hydroxyiminohexyl, 1,1-dimethyl-2-hydroxyiminoethyl, or 2-methyl-3-hydroxyiminopropyl group. And a hydroxyiminoalkyl group which is an alkyl group.

As the halogen-substituted lower alkoxy group,
For example, 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
Carbon number having 1 to 3 halogen atoms such as trichlorobutoxy, 4-fluorobutoxy, 5-chloropentyloxy, 3-chloro-2-methylpropoxy, 6-bromohexyloxy, and 5,6-dichlorohexyloxy group Examples include 1 to 6 straight-chain or branched alkoxy groups.

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

A group selected from the group consisting of a hydroxyl group and an amino group which may have a lower alkyl group as a substituent is 1
Examples of the lower alkoxy group having 2 to 2 lower alkoxy groups include hydroxymethoxymethoxy, 3- (2-hydroxyethoxy) propoxy, 4- (1-hydroxyethoxy) butoxy, 6- (3-hydroxypropoxy) hexyloxy, 5- ( 2,3-dihydroxypropoxy)
Pentyloxy, 1,1-dimethyl-2- (4-hydroxybutoxy) ethoxy, 2-methyl-3- (3,4-
Dihydroxybutoxy) propoxy, 2- (1,1-dimethyl-2-hydroxyethoxy) ethoxy, (5-hydroxypentyloxy) methoxy, 6-hydroxyhexyloxymethoxy, (2-methyl-3-hydroxypropoxy) methoxy, amino Methoxymethoxy, 2-
(1-aminoethoxy) ethoxy, 1- (2-aminoethoxy) ethoxy, 3- (3-aminopropoxy) propoxy, 4- (4-aminobutoxy) butoxy, 5-
(5-aminopentyloxy) pentyloxy, 6-
(6-aminohexyloxy) hexyloxy, (1,
1-dimethyl-2-aminoethoxy) methoxy, (2-
Methyl-3-aminopropoxy) methoxy, 1,1-dimethyl-2- (methylaminomethoxy) ethoxy, 2-
Methyl-3- (ethylaminomethoxy) propoxy, propylaminomethoxymethoxy, 1- (isopropylaminomethoxy) ethoxy, 2- (butylaminomethoxy) ethoxy, 3- (tert-butylaminomethoxy) propoxy, 4- (pentylamino) Methoxy) butoxy,
5- (hexylaminomethoxy) pentyloxy, 6-
(Dimethylaminomethoxy) hexyloxy, 1,1-
Dimethyl-2- (diethylaminomethoxy) ethoxy,
2-methyl-3- (dipropylaminomethoxy) propoxy, dibutylaminomethoxymethoxy, 1- (dipentylaminomethoxy) ethoxy, 2- (dihexylaminomethoxy) ethoxy, 3- (N-methyl-N-ethylaminomethoxy) Propoxy, 4- (N-methyl-N-
Propylaminomethoxy) butoxy, 5- (N-methyl-N-butylaminomethoxy) pentyloxy, 6-
(N-methyl-N-hexylaminomethoxy) hexyloxy, (1-methylaminoethoxy) methoxy, 1-
(2-ethylaminoethoxy) ethoxy, 2- (3-propylaminopropoxy) ethoxy, 3- (4-butylaminobutoxy) propoxy, 4- (1,1-dimethyl-2-pentylaminoethoxy) butoxy, 5- (5-
Hexylaminopentyloxy) pentyloxy, 6-
(6-dimethylaminohexyloxy) hexyloxy, 3- (2-diethylaminoethoxy) propoxy,
4- [1- (N-methyl-N-hexylamino) ethoxy] butoxy, 5- (3-dihexylaminopropoxy) pentyloxy, 6- (4-dibutylaminobutoxy) hexyloxy, 3- [2- (N -Methyl-N-pentylamino) ethoxy] propoxy, 5- (2-hydroxy-3-dimethylaminopropoxy) pentyloxy, 5- (2-hydroxy-3-diethylaminopropoxy) pentyloxy, 3- (2-hydroxy- 3-diethylaminopropoxy) propoxy, 4- (3-hydroxy-4-methylaminobutoxy) butoxy, 5-
A hydroxyl group such as (4-hydroxy-5-dimethylaminopentyloxy) pentyloxy, 6- (4-hydroxy-5-methylaminopentyloxy) hexyloxy group and a straight-chain or branched group having 1 to 6 carbon atoms as a substituent; A straight-chain or branched alkoxy group having 1 to 6 carbon atoms having 1 to 2 groups selected from the group consisting of amino groups which may have a chain alkyl group; A branched alkoxy group can be exemplified.

The morpholinyl-substituted lower alkoxy group which may have a group selected from the group consisting of a lower alkyl group and an oxo group as a substituent includes, for example, (2-morpholinyl) methoxy, 2- (3-morpholinyl) ethoxy,
1- (3-morpholinyl) ethoxy, 3- (2-morpholinyl) propoxy, 4- (3-morpholinyl) butoxy, 5- (2-morpholinyl) pentyloxy, 6-
(3-morpholinyl) hexyloxy, 1,1-dimethyl-2- (3-morpholinyl) ethoxy, 2-methyl-
3- (2-morpholinyl) propoxy, 6- (1-methyl-5-oxo-3-morpholinyl) hexyloxy,
(1-ethyl-2-morpholinyl) methoxy, 2- (2
-Oxo-3-morpholinyl) ethoxy, 1- (2-propyl-3-morpholinyl) ethoxy, 3- (3-butyl-2-morpholinyl) propoxy, 4- (5-pentyl-3-morpholinyl) butoxy, 5- (6-hexyl-2-morpholinyl) pentyloxy, 3- (5-oxo-1-propyl-2-morpholinyl) propoxy,
-(2-oxo-1-butyl-3-morpholinyl) butoxy, 5- (3-oxo-1-pentyl-6-morpholinyl) pentyloxy, 6- (2-oxo-1-hexyl-5-morpholinyl) hexyl A morpholinyl-substituted straight-chain having 1 to 6 carbon atoms which may have 1 to 2 groups selected from the group consisting of a linear or branched alkyl group having 1 to 6 carbon atoms and an oxo group as a substituent such as an oxy group. A chain or branched alkoxy group can be exemplified.

Examples of the benzimidazolylthio-substituted lower alkoxy group include (benzimidazol-2-yl) thiomethoxy, 1- (benzimidazol-4-yl) thioethoxy, 2- (benzimidazol-5-yl) thioethoxy, and 3- (benzimidazol-5-yl) thioethoxy. (Benzimidazol-6-yl) thiopropoxy, 4- (benzimidazol-2-
Yl) thiobutoxy, 5- (benzimidazole-7-
Yl) thiopentyloxy, 6- (benzimidazol-2-yl) thiohexyloxy, 1,1-dimethyl-
2- (benzimidazol-2-yl) thioethoxy,
Examples thereof include a benzimidazolylthio-substituted linear or branched alkoxy group having 1 to 6 carbon atoms such as a 2-methyl-3- (benzimidazol-2-yl) thiopropoxy group.

The benzimidazolylsulfinyl-substituted lower alkoxy group includes, for example, (benzimidazole-
2-yl) sulfinylmethoxy, 1- (benzimidazol-4-yl) sulfinylethoxy, 3- (benzimidazol-6-yl) sulfinylpropoxy,
4- (benzimidazol-2-yl) sulfinylbutoxy, 5- (benzimidazol-7-yl) sulfinylpentyloxy, 6- (benzimidazol-2)
-Yl) sulfinylhexyloxy, 1,1-dimethyl-2- (benzimidazol-2-yl) sulfinylethoxy, 2-methyl-3- (benzimidazole-
Examples thereof include a benzimidazolylsulfinyl-substituted linear or branched alkoxy group having 1 to 6 carbon atoms such as 2-yl) sulfinylpropoxy group.

Examples of the tetrahydropyranyl lower alkyl group include (2-, 3- or 4-tetrahydropyranyl) methyl, 2- (2-, 3- or 4-tetrahydropyranyl) ethyl, 1- (2- , 3- or 4-tetrahydropyranyl) ethyl, 3- (2-, 3- or 4-tetrahydropyranyl) propyl, 4- (2-, 3- or 4-
Tetrahydropyranyl) butyl, 5- (2-, 3- or 4-tetrahydropyranyl) pentyl, 6- (2-, 3
-Or 4-tetrahydropyranyl) hexyl, 1,1-
Dimethyl-2- (2-, 3- or 4-tetrahydropyranyl) ethyl, 2-methyl-3- (2-, 3- or 4-
Examples thereof include a tetrahydropyranylalkyl group in which the alkyl portion such as a (tetrahydropyranyl) propyl group is a linear or branched alkyl group having 1 to 6 carbon atoms.

Examples of the 5- or 6-membered saturated heterocyclic group formed by bonding to each other via a nitrogen atom, an oxygen atom or a sulfur atom together with or without a nitrogen atom to which R ¹⁴ and R ¹⁵ are bonded include pyrrolidinyl , Piperidinyl, piperazinyl, morpholino and thiomorpholino groups.

Examples of the heterocyclic group substituted by a group selected from the group consisting of a carbamoyl group, a lower alkyl group, a phenyl lower alkyl group, a phenyl group and a hydroxyl-substituted lower alkyl group include 4-phenylpiperazinyl and 2-phenylpiperazinyl. Phenylpyrrolidinyl, 4-phenylpiperidinyl, 3-phenylmorpholino, 3-phenylthiomorpholino, 4-benzylpiperazinyl, 3- (2-phenylethyl) pyrrolidinyl, 2- (3-phenylpropyl) pyrrolidinyl, 4- (4-phenylbutyl) piperidinyl, 3-
(5-phenylpentyl) morpholino, 2- (6-phenylhexyl) thiomorpholinyl, 4-methylpiperazinyl, 3,4-dimethylpiperazinyl, 3-ethylpyrrolidinyl, 2-propylpyrrolidinyl, 3, 4,5-trimethylpiperidinyl, 4-butylpiperidinyl, 3-
Pentylmorpholinyl, 2-hexylthiomorpholino,
4-ethylpiperazinyl, 3-methyl-4-phenylpiperazinyl, 3-ethyl-4-benzylpiperidinyl,
3-methyl-4-benzylpyrrolidinyl, 3-methyl-
5-phenylmorpholino, 3-methyl-5- (2-hydroxyethyl) thiomorpholino, 4- (2-hydroxyethyl) piperazinyl, 2- (hydroxymethyl) pyrrolidinyl, 4- (4-hydroxybutyl) piperidinyl, 2- (5-hydroxypentyl) thiomorpholino,
3- (6-hydroxyhexyl) morpholino, 2-methyl-4- (2-hydroxyethyl) pyrrolidinyl, 2-
Carbamoylpyrrolidinyl, 3-carbamoylpyrrolidinyl, 4-carbamoylpiperazinyl, 3-carbamoylpiperazinyl, 2-carbamoylpiperazinyl, 4-
Carbamoylpiperidinyl, 3-carbamoylpiperidinyl, 2-carbamoylpiperidinyl, 3-carbamoylmorpholino, 2-carbamoylthiomorpholino, 2-carbamoylthiomorpholino
Methyl-3-carbamoylpyrrolidinyl, 3-methyl-
4-carbamoylpiperidinyl, 2,6-dimethyl-4
-A carbamoyl group such as a carbamoylpiperazinyl group, a linear or branched alkyl group having 1 to 6 carbon atoms, a phenylalkyl group in which the alkyl portion is a linear or branched alkyl group having 1 to 6 carbon atoms And the above-mentioned heterocyclic group in which 1 to 3 groups selected from the group consisting of a linear or branched alkyl group having 1 to 6 carbon atoms and a phenyl group and a hydroxyl group are substituted.

Examples of the amino group which may have a phenyl lower alkoxycarbonyl group as a substituent include, for example, amino, benzyloxycarbonylamino, (2-phenylethoxycarbonyl) amino, (1-phenylethoxycarbonyl) amino, (3- Phenylpropoxycarbonyl) amino, (4-phenylbutoxycarbonyl) amino, (5-phenylpentyloxycarbonyl) amino, (6-phenylhexyloxycarbonyl) amino, (1,1-dimethyl-2-phenylethoxycarbonyl) amino, (2-methyl-3-phenylpropoxycarbonyl) having a phenylalkoxycarbonyl group in which the alkoxycarbonyl group is a straight-chain or branched-chain alkoxycarbonyl group having 1 to 6 carbon atoms as a substituent such as an amino group. It can be exemplified certain amino group.

The phenyl group which may have a hydroxyl group as a substituent on the phenyl ring includes, for example, phenyl, 4
-Hydroxyphenyl, 3-hydroxyphenyl, 2-
Hydroxyphenyl, 2,4-dihydroxyphenyl,
A phenyl group which may have 1 to 3 hydroxyl groups as a substituent on a phenyl ring such as 3,4-dihydroxyphenyl or 2,3,4-trihydroxyphenyl group can be exemplified.

A group selected from the group consisting of an amino group which may have one or two groups selected from the group consisting of a lower alkyl group, a nitro group, and a lower alkyl group and a lower alkanoyl group on a phenyl ring. Examples of the phenylsulfonyl group which may have phenylsulfonyl, 2-methylphenylsulfonyl, 3-methylphenylsulfonyl, 4-methylphenylsulfonyl, 2-ethylphenylsulfonyl, 3-ethylphenylsulfonyl, 4-ethylphenylsulfonyl 4-isopropylphenylsulfonyl, 4-butylphenylsulfonyl,
2-pentylphenylsulfonyl, 3-hexylphenylsulfonyl, 2,4-dimethylphenylsulfonyl,
3,4-diethylphenylsulfonyl, 3,4,5-trimethylphenylsulfonyl, 4-aminophenylsulfonyl, 3-aminophenylsulfonyl, 2-aminophenylsulfonyl, 3,4-diaminophenylsulfonyl, 2,5-diaminophenyl Sulfonyl, 2,4,6
-Triaminophenylsulfonyl, 4-nitrophenylsulfonyl, 3-nitrophenylsulfonyl, 2-nitrophenylsulfonyl, 2,3-dinitrophenylsulfonyl, 2,6-dinitrophenylsulfonyl, 2,
4,6-trinitrophenylsulfonyl, 4-acetylaminophenylsulfonyl, 4-dimethylaminophenylsulfonyl, 3- (N-methyl-N-acetylamino) phenylsulfonyl, 2-methyl-4-aminophenylsulfonyl, 3- A straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms as a substituent on a phenyl ring such as nitro-4-methylphenylsulfonyl, 2-ethylaminophenylsulfonyl, 2-methyl-3-diethylaminophenylsulfonyl, Having 1 to 2 groups selected from the group consisting of a nitro group, a linear or branched alkyl group having 1 to 6 carbon atoms and a linear or branched alkanoyl group having 1 to 6 carbon atoms. A group selected from the group consisting of a certain amino group
And a phenylsulfonyl group which may be present.

Examples of the amino lower alkyl group which may have a substituent selected from the group consisting of a lower alkyl group and a lower alkanoyl group include aminomethyl, 2-aminoethyl, 1-aminoethyl, 3-aminopropyl, 4
-Aminobutyl, 5-aminopentyl, 6-aminohexyl, 1,1-dimethyl-2-aminoethyl, 2-methyl-3-aminopropyl, methylaminomethyl, 1-ethylaminoethyl, 2-propylaminoethyl, 3-isopropylaminopropyl, 4-butylaminobutyl,
5-pentylaminopentyl, 6-hexylaminohexyl, dimethylaminomethyl, (N-ethyl-N-propylamino) methyl, 2- (N-methyl-N-hexylamino) ethyl, 2- (acetylamino) ethyl, 3-
(Acetylamino) propyl, formylaminomethyl,
1- (propionylamino) ethyl, 4- (butyrylamino) butyl, 5- (pentanoylamino) pentyl,
6- (hexanoylamino) hexyl, 2- (N-methyl-N-acetylamino) ethyl, 1- (N-ethyl-
A linear or branched alkyl group having 1 to 6 carbon atoms as a substituent such as an N-acetylamino) ethyl group;
And a straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms and having an amino group which may have 1 to 2 groups selected from the group consisting of a straight-chain or branched-chain alkanoyl group.

Examples of the piperidinyl group which may have a phenyl lower alkyl group as the substituent include, for example, 4-piperidinyl, 3-piperidinyl, 2-piperidinyl,
-Benzyl-4-piperidinyl, 1- (2-phenylethyl) -3-piperidinyl, 2- (3-phenylpropyl) -5-piperidinyl, 3- (4-phenylbutyl)
-6-piperidinyl, 4- (5-phenylpentyl)-
3-piperidinyl, 5- (6-phenylhexyl) -4
-Piperidinyl, 2-benzyl-4-piperidinyl, 1
Examples of the substituent such as-(3-phenylpropyl) -4-piperidinyl include a piperidinyl group which may have a phenylalkyl group in which the alkyl portion is a linear or branched alkyl group having 1 to 6 carbon atoms.

Examples of the imidazo [4,5-c] pyridylcarbonyl lower alkoxy group include, for example, (imidazo [4,5-c] pyridylcarbonyl
5-c] pyridin-2-yl) carbonylmethoxy, 2
-(Imidazo [4,5-c] pyridin-2-yl) carbonylethoxy, 1- (imidazo [4,5-c] pyridin-4-yl) carbonylethoxy, 3- (imidazo [4,5-c] Pyridin-5-yl) carbonylpropoxy, 4- (imidazo [4,5-c] pyridin-7-yl) carbonylbutoxy, 5- (imidazo [4,5-
c] pyridin-2-yl) carbonylpentyloxy,
6- (imidazo [4,5-c] pyridin-2-yl) carbonylhexyloxy, 1,1-dimethyl-2- (imidazo [4,5-c] pyridin-2-yl) carbonylethoxy, 2-methyl -3- (imidazo [4,5-c]
An imidazo [4,5-c] pyridylcarbonylalkoxy group in which the alkoxy moiety such as a pyridin-2-yl) carbonylpropoxy group is a linear or branched alkoxy group having 1 to 6 carbon atoms.

Examples of the tri-lower alkyl ammonium group include, for example, trimethyl ammonium, triethyl ammonium, tripropyl ammonium, triisopropyl ammonium, tributyl ammonium, tri-tert-
Butyl ammonium, tripentyl ammonium, trihexylammonium, dimethyl, ethyl ammonium, diethyl, propyl ammonium, dimethyl, butyl ammonium, diethyl, methyl ammonium, dimethyl, hexyl ammonium, dipropyl, methyl ammonium, dibutyl, ethyl ammonium, methyl, ethyl, Examples thereof include ammonium groups having three straight or branched alkyl groups having 1 to 6 carbon atoms, such as propylammonium, methyl, butyl, and pentylammonium.

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

Examples of the lower alkyl group which may have a hydroxyl group or a cyano group as a substituent include, for example, hydroxymethyl, 2-hydroxyethyl, 1-hydroxyethyl, 3-hydroxypropyl, 3-dihydroxypropyl, 4-hydroxybutyl, 1,1-dimethyl-2-hydroxyethyl, 5,
5,4-trihydroxypentyl, 5-hydroxypentyl, 6-hydroxyhexyl, 1-hydroxyisopropyl, 2-methyl-3-hydroxypropyl, 2,3
-Dihydroxyethyl, 3,4-dihydroxybutyl,
5,6-dihydroxyhexyl, cyanomethyl, 2-cyanoethyl, 1-cyanoethyl, 3-cyanopropyl,
Having 1 to 3 hydroxyl groups or cyano groups as substituents such as 4-cyanobutyl, 5-cyanopentyl, 6-cyanohexyl, 1,1-dimethyl-2-cyanoethyl and 2-methyl-3-cyanopropyl groups; A linear or branched alkyl group having 1 to 6 carbon atoms can be exemplified.

Examples of the lower alkynyl group include ethynyl, 2-propynyl, 2-butynyl, 3-butynyl,
Examples thereof include a linear or branched alkynyl group having 2 to 6 carbon atoms such as -methyl-2-propynyl, 2-pentynyl, and 2-hexynyl group.

Examples of the pyrrolidinylcarbonyl group which may have a phenyl lower alkoxycarbonyl group as a substituent on the pyrrolidine ring include, for example, 1-benzyloxycarbonyl-2-pyrrolidinylcarbonyl, 2-pyrrolidinylcarbonyl, -Pyrrolidinylcarbonyl, 3-
Pyrrolidinylcarbonyl, 1- (2-phenylethoxycarbonyl) -2-pyrrolidinylcarbonyl, 2- (1
-Phenylethoxycarbonyl) -1-pyrrolidinylcarbonyl, 3- (3-phenylpropoxycarbonyl)
-2-pyrrolidinylcarbonyl, 1- (4-phenylbutoxycarbonyl) -2-pyrrolidinylcarbonyl, 2
A lower alkoxy group moiety as a substituent on a pyrrolidine ring such as-(5-phenylpentyloxycarbonyl) -1-pyrrolidinylcarbonyl, 2- (6-phenylhexyloxycarbonyl) -3-pyrrolidinylcarbonyl group is a carbon atom; Examples thereof include a pyrrolidinylcarbonyl group which may have a phenylalkoxycarbonyl group, which is a straight-chain or branched-chain alkoxy group of Formulas 1 to 6.

Examples of the phenyl lower alkoxycarbonylamino group include N-benzyloxycarbonylamino, N- (2-phenylethoxycarbonyl) amino,
N- (1-phenylethoxycarbonyl) amino, N-
(3-phenylpropoxycarbonyl) amino, N-
(4-phenylbutoxycarbonyl) amino, N- (5
-Phenylpentyloxycarbonyl) amino, N-
(6-phenylhexyloxycarbonyl) amino, N
A lower alkoxycarbonyl group moiety such as-(1,1-dimethyl-2-phenylethoxycarbonyl) amino, N- (2-methyl-3-phenylpropoxycarbonyl) amino group has a straight or branched chain having 1 to 6 carbon atoms; A phenylalkoxycarbonylamino group which is a chain alkoxycarbonyl group can be exemplified.

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

As the hydroxyl-substituted lower alkanoyl group,
For example, 2-hydroxyacetyl, 3-hydroxypropionyl, 2-hydroxypropionyl, 4-hydroxybutyryl, 2,2-dimethyl-3-hydroxypropionyl, 5-hydroxypentanoyl, 6-hydroxyhexanoyl, 3-methyl-4 -A straight-chain or branched-chain alkanoyl group having 2 to 6 carbon atoms, such as a hydroxybutyryl group, can be exemplified.

The lower alkanoyloxy lower alkanoyl group includes, for example, 2-acetyloxyacetyl,
Propionyloxypropionyl, 2-butyryloxypropionyl, 4-pentanoyloxybutyryl, 2,
2-dimethyl-3-hexanoyloxypropionyl,
A straight-chain or branched alkanoyloxy group having 2 to 6 carbon atoms, such as a 5-acetyloxypentanoyl or 6-propionyloxyhexanoyl group; and a straight-chain or branched alkanoyl group having 2 to 6 carbon atoms. it can.

The phenyl lower alkyl group which may have a lower alkoxy group as a substituent on the phenyl ring includes, for example, 2-phenyl in addition to the above-mentioned phenyl lower alkyl group.
Methoxybenzyl, 3-methoxybenzyl, 2- (4-
Methoxyphenyl) ethyl, 1- (2-ethoxyphenyl) ethyl, 3- (4-isopropoxyphenyl) propyl, 4- (3-pentyloxyphenyl) butyl,
-(4-hexyloxyphenyl) pentyl, 6- (2
-Butyloxyphenyl) hexyl, 3,4-dimethoxybenzyl, 3-ethoxy-4-methoxybenzyl,
A linear or branched alkoxy group having 1 to 6 carbon atoms as a substituent on a phenyl ring such as 2,3-dimethoxybenzyl, 2,6-dimethoxybenzyl, 3,4,5-trimethoxybenzyl, etc. Examples thereof include a phenylalkyl group which is a straight or branched alkyl group having 1 to 6 carbon atoms in the alkyl moiety which may have up to 3 carbon atoms.

As the cycloalkenylcarbonyl group,
Examples thereof include cycloalkenylcarbonyl groups having 3 to 8 carbon atoms, such as cyclopropenylcarbonyl, cyclobutenylcarbonyl, cyclopentenylcarbonyl, cyclohexenylcarbonyl, cycloheptenylcarbonyl, and cyclooctenylcarbonyl.

Examples of the pyrimidylthio lower alkoxy group include (2-pyrimidyl) thiomethoxy and 2- (4
-Pyrimidyl) thioethoxy, 1- (5-pyrimidyl)
Thioethoxy, 3- (6-pyrimidyl) thiopropoxy, 4- (4-pyrimidyl) thiobutoxy, 5- (2-
Pyrimidyl) thiopentyloxy, 6- (5-pyrimidyl) thiohexyloxy, 1,1-dimethyl-2- (2
-Pyrimidyl) thioethoxy, 2-methyl-3- (2-
A pyrimidylthioalkoxy group in which the alkoxy moiety such as (pyrimidyl) thiopropoxy group is a linear or branched alkoxy group having 1 to 6 carbon atoms can be exemplified.

Examples of the pyrimidylsulfinyl lower alkoxy group include (2-pyrimidyl) sulfinylmethoxy, 2- (4-pyrimidyl) sulfinylethoxy,
1- (5-pyrimidyl) sulfinylethoxy, 3-
(6-pyrimidyl) sulfinylpropoxy, 4- (4
-Pyrimidyl) sulfinylbutoxy, 5- (2-pyrimidyl) sulfinylpentyloxy, 6- (5-pyrimidyl) sulfinylhexyloxy, 1,1-dimethyl-2- (2-pyrimidyl) sulfinylethoxy, 2
Examples thereof include a pyrimidylsulfinylalkoxy group in which the lower alkoxy moiety such as -methyl-3- (2-pyrimidyl) sulfinylpropoxy group is a linear or branched alkoxy group having 1 to 6 carbon atoms.

Examples of the pyrimidylsulfonyl lower alkoxy group include (2-pyrimidyl) sulfonylmethoxy, 2- (4-pyrimidyl) sulfonylethoxy, 1-
(5-pyrimidyl) sulfonylethoxy, 3- (6-pyrimidyl) sulfonylpropoxy, 4- (4-pyrimidyl) sulfonylbutoxy, 5- (2-pyrimidyl) sulfonylpentyloxy, 6- (5-pyrimidyl) sulfonylhexyloxy, 1,1-dimethyl-2- (2-pyrimidyl) sulfonylethoxy, 2-methyl-3- (2
A pyrimidylsulfonylalkoxy group in which the lower alkoxy moiety such as-(pyrimidyl) sulfonylpropoxy group is a linear or branched alkoxy group having 1 to 6 carbon atoms.

The imidazolylthio lower alkoxy group which may have a lower alkyl group as a substituent includes, for example, (2-imidazolyl) thiomethoxy, 2- (4-imidazolyl) thioethoxy, 1- (5-imidazolyl)
Thioethoxy, 3- (2-imidazolyl) thiopropoxy, 4- (4-imidazolyl) thiobutoxy, 5- (2
-Imidazolyl) thiopentyloxy, 6- (5-imidazolyl) thiohexyloxy, 1,1-dimethyl-2
-(2-imidazolyl) thioethoxy, 2-methyl-3
-(2-imidazolyl) thiopropoxy, (4-methyl-2-imidazolyl) thioethoxy, 2- (5-ethyl-4-imidazolyl) thioethoxy, 1- (4-propyl-5-imidazolyl) thioethoxy, 3- (1 -Butyl-2-imidazolyl) thiopropoxy, 4- (2-pentyl-4-imidazolyl) thiobutoxy, 5- (1-
Methyl-2-imidazolyl) thiopentyloxy, 6-
(1-hexyl-5-imidazolyl) thiohexyloxy, 1,1-dimethyl-2- (1-ethyl-2-imidazolyl) thioethoxy, 2-methyl-3- (1-propyl-2-imidazolyl) thiopropoxy group An imidazolylthioalkoxy group in which the lower alkoxy moiety which may have a straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms is a straight-chain or branched-chain alkoxy group having 1 to 6 carbon atoms Can be exemplified.

The imidazolylsulfonyl lower alkoxy group which may have a lower alkyl group as a substituent includes, for example, (2-imidazolyl) sulfonylmethoxy,
2- (4-imidazolyl) sulfonylethoxy, 1-
(5-imidazolyl) sulfonylethoxy, 3- (2-
Imidazolyl) sulfonylpropoxy, 4- (4-imidazolyl) sulfonylbutoxy, 5- (2-imidazolyl) sulfonylpentyloxy, 6- (5-imidazolyl) sulfonylhexyloxy, 1,1-dimethyl-2
-(2-imidazolyl) sulfonylethoxy, 2-methyl-3- (2-imidazolyl) sulfonylpropoxy,
(4-methyl-2-imidazolyl) sulfonylmethoxy, 2- (5-ethyl-4-imidazolyl) sulfonylethoxy, 1- (4-propyl-5-imidazolyl) sulfonylethoxy, 3- (1-butyl-2-imidazolyl) ) Sulfonylpropoxy, 4- (2-pentyl-4-)
Imidazolyl) sulfonylbutoxy, 5- (1-methyl-2-imidazolyl) sulfonylpentyloxy, 6-
(1-hexyl-5-imidazolyl) sulfonylhexyloxy, 1,1-dimethyl-2- (1-ethyl-2-
Imidazolyl) sulfonylethoxy, 2-methyl-3-
A lower alkoxy moiety which may have a linear or branched alkyl group having 1 to 6 carbon atoms as a substituent such as a (1-propyl-2-imidazolyl) sulfonylpropoxy group is a straight-chain having 1 to 6 carbon atoms or An example is an imidazolylsulfonylalkoxy group which is a branched alkoxy group.

Examples of the ammonium lower alkoxy group having three groups selected from the group consisting of a lower alkyl group, a lower alkenyl group and an oxo group include, for example, trimethylammonium methoxy, 2- (triethylammonium) ethoxy, 1- (tripropylammonium) ) Ethoxy, 3-
(Tributylammonium) propoxy, 4- (tripentylammonium) butoxy, 5- (triethylammonium) pentyloxy, 6- (trihexylammonium) hexyloxy, 1,1-dimethyl-2- (triallylammonium) ethoxy, -Methyl-3-
(Tributenyl ammonium) propoxy, tri (1-
Methylallyl) ammonium methoxy, 2- [tri (2
-Pentenyl) ammonium] ethoxy, 1- [tri (2-hexenyl) ammonium] ethoxy, 3- (N
-Allyl-N, N-dimethylammonium) propoxy, 4- (N, N-diallyl-N-methyl) butoxy,
5- (N-allyl-N-methylamino) pentyloxy N-oxide, 6- (N-allyl-N-ethylamino) hexyloxy N-oxide, 5- (N-allyl-N-methyl-N-ethyl) Ammonium) a linear or branched alkyl group having 1 to 6 carbon atoms such as a pentyloxy group;
A lower alkoxy group having three groups selected from the group consisting of a linear or branched alkenyl group having 2 to 6 carbon atoms and an oxo group is a linear or branched alkoxy group having 1 to 6 carbon atoms; A certain ammonium alkoxy group can be exemplified.

Examples of the phenylthio lower alkoxy group which may have a substituent selected from the group consisting of a nitro group and an amino group on the phenyl ring include, for example, phenylthiomethoxy, 2-phenylthioethoxy and 1-phenylthioethoxy. , 3-phenylthiopropoxy, 4-phenylthiobutoxy, 5-phenylthiopentyloxy,
6-phenylthiohexyloxy, 1,1-dimethyl-
2-phenylthioethoxy, 2-methyl-3-phenylthiopropoxy, (2-nitrophenyl) thiomethoxy, 2- (3-nitrophenyl) thioethoxy, 1-
(4-nitrophenyl) thioethoxy, 3- (2,3-
Dinitrophenyl) thiopropoxy, 4- (3,4-dinitrophenyl) thiobutoxy, 5- (4-nitrophenyl) thiopentyloxy, 6- (2,6-dinitrophenyl) hexyloxy, 1,1-dimethyl-2 −
(2,4,6-trinitrophenyl) ethoxy, 2-methyl-3- (4-nitrophenyl) propoxy, (2-
Aminophenyl) thiomethoxy, 2- (3-aminophenyl) thioethoxy, 1- (4-aminophenyl) thioethoxy, 3- (2,3-diaminophenyl) thiopropoxy, 4- (3,4-diaminophenyl) thiobutoxy, 5- (4-aminophenyl) thiopentyloxy,
6- (2,6-diaminophenyl) thiohexyloxy, 1,1-dimethyl-2- (2,4,6-triaminophenyl) thioethoxy, 2-methyl-3- (4-aminophenyl) thiopropoxy group A lower alkoxy moiety which may have 1 to 3 groups selected from the group consisting of a nitro group and an amino group as a substituent on the phenyl ring is a linear or branched alkoxy group having 1 to 6 carbon atoms. A certain phenylthioalkoxy group can be exemplified.

A nitro group as a substituent and a group selected from an amino group which may have one or two groups selected from a lower alkanoyl group and a lower alkyl group as a substituent on a phenyl ring; Possible phenylsulfonyl lower alkoxy groups include, for example, phenylsulfonylmethoxy, 2-phenylsulfonylethoxy,
1-phenylsulfonylethoxy, 3-phenylsulfonylpropoxy, 4-phenylsulfonylbutoxy, 5
-Phenylsulfonylpentyloxy, 6-phenylsulfonylhexyloxy, 1,1-dimethyl-2-phenylsulfonylethoxy, 2-methyl-3-phenylsulfonylpropoxy, (2-aminophenyl) sulfonylmethoxy, 5- (4-amino Phenyl) sulfonylpentyloxy, 2- (4-methylaminophenyl) sulfonylethoxy, 1- (3-ethylaminophenyl) sulfonylethoxy, 3- [2- (N-methyl-N-ethylamino) phenyl] sulfonylpropoxy, 4- [3
-(N-methyl-N-hexylamino) phenyl] sulfonylbutoxy, 5- (4-dimethylaminophenyl)
Sulfonylpentyloxy, 4-dipentylaminophenylsulfonylmethoxy, 2- (2-isopropylaminophenyl) sulfonylethoxy, 1- (3-butylaminophenyl) sulfonylethoxy, 5- (2,4-diaminophenyl) sulfonylpentyloxy, 3-
[2,3-bis (dimethylamino) phenyl] sulfonylpropoxy, 4- [3,4-bis (methylamino) phenyl] sulfonylbutoxy, 5- (2,4,6-triaminophenyl) sulfonylpentyloxy, 6 −
[3,4,5-tri (methylamino) phenyl] sulfonylhexyloxy, 5- (4-acetylaminophenyl) sulfonylpentyloxy, 3- [4- (N-methyl-N-acetylamino) phenyl] sulfonylpropoxy , 5- (4-nitrophenyl) sulfonylpentyloxy, 2- (4-nitro-3-methylaminophenyl) sulfonylethoxy, 3- (2,4-dinitrophenyl) sulfonylpropoxy, 4- (2,4,6 A group consisting of a linear or branched alkyl group having 1 to 6 carbon atoms and a linear or branched alkanoyl group having 1 to 6 carbon atoms as substituents on a phenyl ring such as -trinitrophenyl) sulfonylbutoxy group; May have 1 to 2 groups selected from the group consisting of amino and nitro groups which may have 1 to 2 groups selected from Grade alkoxy group can be exemplified phenylsulfonyl alkoxy group is a straight-chain or branched alkoxy group having 1 to 6 carbon atoms. Examples of the pyridylthio lower alkoxy group include (2-pyridyl) thiomethoxy, 2- (3-pyridyl) thioethoxy, 1- (4-pyridyl) thioethoxy, 3- (3-pyridyl) thiopropoxy, and 4- (4-pyridyl) Thioboxy, 5- (2
-Pyridyl) thiopentyloxy, 5- (4-pyridyl) thiopentyloxy, 6- (3-pyridyl) thiohexyloxy, 1,1-dimethyl-2- (2-pyridyl) thioethoxy, 2-methyl-3- (4-pyridyl)
A pyridylthioalkoxy group which is a linear or branched alkoxy group having 1 to 6 carbon atoms in a lower alkoxy group such as a thiopropoxy group can be exemplified.

Examples of the pyridylsulfonyl lower alkoxy group which may have an oxo group on the pyridine ring include, for example, (2-pyridyl) sulfonylmethoxy, 2- (3-pyridyl) sulfonylethoxy, 1- (4-pyridyl) sulfonylethoxy 3- (3-pyridyl) sulfonylpropoxy, 4- (4-pyridyl) sulfonylbutoxy,
5- (2-pyridyl) sulfonylpentyloxy, 5-
(4-pyridyl) sulfonylpentyloxy, 6- (3
-Pyridyl) sulfonylhexyloxy, 1,1-dimethyl-2- (2-pyridyl) sulfonylethoxy, 2-
Methyl-3- (4-pyridyl) sulfonylpropoxy,
5- (1-oxide-4-pyridyl) sulfonylpentyloxy, (4-oxo-2-pyridyl) sulfonylmethoxy, 2- (1-oxo-3-pyridyl) sulfonylethoxy, 1- (2-oxo-4- Pyridyl) sulfonylethoxy, 3- (2-oxo-3-pyridyl) sulfonylpropoxy, 4- (3-oxo-4-pyridyl) sulfonylbutoxy, 5- (1-oxide-2-pyridyl) sulfonylpentyloxy, 6- (1-oxide-
A lower alkoxy group which may have an oxo group on a pyridine ring such as a 3-pyridyl) sulfonylhexyloxy group may be a pyridylsulfonylalkoxy group which is a linear or branched alkoxy group having 1 to 6 carbon atoms.

Examples of the cycloalkylcarbonyl group which may have 1 to 3 groups selected from the group consisting of a hydroxyl group and a lower alkanoyloxy group as a substituent on the cycloalkyl group include, for example, cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentyl Carbonyl, cyclohexylcarbonyl, cycloheptylcarbonyl, cyclooctylcarbonyl, 2-hydroxycyclopropylcarbonyl, 3-hydroxycyclobutylcarbonyl,
-Hydroxycyclopentylcarbonyl, 3-hydroxycyclopentylcarbonyl, 2,4-dihydroxycyclopentylcarbonyl, 2-hydroxycyclohexylcarbonyl, 3-hydroxycyclohexylcarbonyl, 4-hydroxycyclohexylcarbonyl, 3,4
-Dihydroxycyclohexylcarbonyl, 2,4-dihydroxycyclohexylcarbonyl, 2,5-dihydroxycyclohexylcarbonyl, 3,4,5-trihydroxycyclohexylcarbonyl, 3-hydroxycycloheptylcarbonyl, 3,4-dihydroxycycloheptylcarbonyl, 2, 3,4-trihydroxycycloheptylcarbonyl, 4-hydroxycyclooctylcarbonyl, 4,5-dihydroxycyclooctylcarbonyl, 4,5,6-trihydroxycyclooctylcarbonyl, 2-acetyloxycyclopropylcarbonyl, 3-propionyloxy Cyclobutylcarbonyl,
2-butyryloxycyclopentylcarbonyl, 3-pentanoyloxycyclopentylcarbonyl, 2,4-
Dihexanoylcyclopentylcarbonyl, 2-acetyloxycyclohexylcarbonyl, 3-propionyloxycyclohexylcarbonyl, 4-butyryloxycyclohexylcarbonyl, 3,4-diacetyloxycyclohexylcarbonyl, 2,4-diacetyloxycyclohexylcarbonyl, 2,5- Diacetyloxycyclohexylcarbonyl, 3,4,5-triacetyloxycyclohexylcarbonyl, 3,4-diacetyloxy-5-hydroxycyclohexylcarbonyl, 3
Pentanoyloxycycloheptylcarbonyl, 3,
4-diacetyloxycycloheptylcarbonyl, 2,
On cycloalkyl groups such as 3,4-tripropionyloxycycloheptylcarbonyl, 4-hexanoyloxycyclooctylcarbonyl, 4,5-dibutyryloxycyclooctylcarbonyl, and 4,5,6-triacetyloxycyclooctylcarbonyl group Examples of the substituent include a cycloalkyl group having 3 to 8 carbon atoms which may have 1 to 3 groups selected from the group consisting of a hydroxyl group and a linear or branched alkanoyloxy group having 2 to 6 carbon atoms. .

On the tetrahydropyranyl ring, a group selected from the group consisting of a hydroxyl group and a lower alkoxy group is substituted by 1
Examples of the lower alkyl group having 4 to 4 tetrahydropyranyl groups include, for example, (2-tetrahydropyranyl)
Methyl, 2- (3-tetrahydropyranyl) ethyl, 1
-(4-tetrahydropyranyl) ethyl, 3- (2-tetrahydropyranyl) propyl, 4- (3-tetrahydropyranyl) butyl, 5- (4-tetrahydropyranyl) pentyl, 6- (2-tetrahydropyranyl) Hexyl, 1,1-dimethyl-2- (3-tetrahydropyranyl) ethyl, 2-methyl-3- (4-tetrahydropyranyl) propyl, (3-hydroxy-2-tetrahydropyranyl) methyl, -(2,4-dihydroxy-3
-Tetrahydropyranyl) ethyl, 1- (2,3,5-
Trihydroxy-4-tetrahydropyranyl) ethyl,
3- (6-methoxy-2-tetrahydropyranyl) propyl, 4- (4-ethoxy-3-tetrahydropyranyl) butyl, 5- (4,6-dimethoxy-4-tetrahydropyranyl) pentyl, 6- ( 4,5,6-trimethoxy-2-tetrahydropyranyl) hexyl, 1,1-
Dimethyl-2- (2-propoxy-3-tetrahydropyranyl) ethyl, 2-methyl-3- (6-butoxy-4
-Tetrahydropyranyl) propyl, (6-pentyloxy-2-tetrahydropyranyl) methyl, 2- (4-
Hexyloxy-3-tetrahydropyranyl) ethyl,
2- (3,4,5-trihydroxy-6-methoxy-2
-Tetrahydropyranyl) methyl, 1- (3,4,5)
A hydroxyl group and carbon number as substituents on a tetrahydropyranyl ring such as 6-tetrahydroxy-2-tetrahydropyranyl) ethyl and 3- (3,4,5,6-tetramethoxy-2-tetrahydropyranyl) propyl group A group selected from the group consisting of 1 to 6 linear or branched alkoxy groups;
A tetrahydropyranylalkyl group in which the lower alkyl group which may have four is a linear or branched alkyl group having 1 to 6 carbon atoms can be exemplified.

The lower alkanoyl group having a 5- to 6-membered saturated heterocycle selected from the group consisting of pyrrolidinyl, piperazinyl, piperidinyl and morpholinyl groups includes, for example, 2- (1-pyrrolidinyl) acetyl, 3- (2- Pyrrolidinyl) propionyl, 2- (3-pyrrolidinyl)
Propionyl, 4- (1-pyrrolidinyl) butyryl,
2,2-dimethyl-3- (2-pyrrolidinyl) propionyl, 5- (3-pyrrolidinyl) pentanoyl, 6-
(1-pyrrolidinyl) hexanoyl, 2- (1-piperazinyl) acetyl, 3- (2-piperazinyl) propionyl, 2- (3-piperazinyl) propionyl, 4-
(1-piperazinyl) butyryl, 2,2-dimethyl-3
-(2-piperazinyl) propionyl, 5- (3-piperazinyl) pentanoyl, 6- (1-piperazinyl) hexanoyl, 2- (1-piperidinyl) acetyl, 3-
(2-piperidinyl) propionyl, 2- (3-piperidinyl) propionyl, 4- (4-piperidinyl) butyryl, 2,2-dimethyl-3- (1-piperidinyl) propionyl, 5- (2-piperidinyl) pentanoyl,
6- (3-piperidinyl) hexanoyl, 2- (4-morpholino) acetyl, 3- (2-morpholinyl) propionyl, 2- (3-morpholinyl) propionyl, 4-
(4-morpholino) butyryl, 2,2-dimethyl-3-
Pyrrolidinyl wherein the lower alkanoyl moiety such as (2-morpholinyl) propionyl, 5- (3-morpholinyl) pentanoyl, 6- (4-morpholino) hexanoyl is a straight or branched alkanoyl group having 2 to 6 carbon atoms; Examples thereof include an alkanoyl group having a 5- to 6-membered saturated heterocyclic ring selected from the group consisting of piperazinyl, piperidinyl and morpholinyl groups.

Examples of the heterocyclic-substituted lower alkanoyl group having a group selected from the group consisting of a lower alkyl group and a phenyl group as a substituent include, for example, 2- (2-methyl-1-
Pyrrolidinyl) acetyl, 3- (1-ethyl-2-pyrrolidinyl) propionyl, 2- (1-propyl-3-pyrrolidinyl) propionyl, 4- (3-butyl-1-pyrrolidinyl) butyryl, 2,2-dimethyl-3 − (4-
Pentyl-2-pyrrolidinyl) propionyl, 5- (1
-Hexyl-3-pyrrolidinyl) pentanoyl, 6-
(2,3-dimethyl-1-pyrrolidinyl) hexanoyl, 2- (2,3,4-trimethyl-1-pyrrolidinyl) acetyl, 3- (1-phenyl-2-pyrrolidinyl) propionyl, 2- (1-methyl- 2-phenyl-
3-pyrrolidinyl) propionyl, 2- (4-methyl-
1-piperazinyl) acetyl, 2- (4-phenyl-1)
-Piperazinyl) acetyl, 3- (4-ethyl-2-piperazinyl) propionyl, 2- (4-propyl-3-
Piperazinyl) propionyl, 4- (4-butyl-1-)
Piperazinyl) butyryl, 2,2-dimethyl-3- (4
-Pentyl-2-piperazinyl) propionyl, 5-
(4-hexyl-3-piperazinyl) pentanoyl, 6
-(2,4-dimethyl-1-piperazinyl) hexanoyl, 2- (3,4,5-trimethyl-1-piperazinyl) acetyl, 2- (4-phenyl-3-methyl-1-
Piperazinyl) acetyl, 2- (4-methyl-1-piperidino) acetyl, 3- (1-ethyl-2-piperidinyl) propionyl, 2- (1-propyl-3-piperidinyl) propionyl, 4- (1-butyl- 4-piperidinyl) butyryl, 2,2-dimethyl-3- (4-pentyl-1-piperidino) propionyl, 5- (1-hexyl-2-piperidinyl) pentanoyl, 6- (1-phenyl-3-piperidinyl) hexanoyl , 2- (2,5
-Dimethyl-4-phenyl-1-piperidino) acetyl, 2- (2,3,4-trimethyl-1-piperidino)
Acetyl, 2- (1,2-dimethyl-4-piperidinyl) acetyl, 2- (3-methyl-4-morpholino) acetyl, 3- (1-ethyl-2-morpholinyl) propionyl, 2- (1-propyl- 3-morpholinyl) propionyl, 4- (2-butyl-4-morpholino) butyryl, 2,2-dimethyl-3- (1-pentyl-2-morpholinyl) propionyl, 5- (2-hexyl-3-morpholinyl) pentanoyl , 6- (3,5-dimethyl-
4- (morpholino) hexanoyl, 2- (2,3,5-trimethyl-4-morpholino) acetyl, 2- (3-phenyl-4-morpholino) acetyl, 2- (2-methyl-
3-phenyl-4-morpholinyl) the above heterocyclic substitution having 1 to 3 groups selected from the group consisting of a linear or branched alkyl group having 1 to 6 carbon atoms and a phenyl group as a substituent such as an acetyl group; A linear or branched alkanoyl group having 2 to 6 carbon atoms can be exemplified.

Examples of the piperidinylcarbonyl group which may have a lower alkanoyl group as a substituent include (1-piperidino) carbonyl and (2-piperidinyl)
Carbonyl, (3-piperidinyl) carbonyl, (4-
(Piperidinyl) carbonyl, (1-acetyl-4-piperidinyl) carbonyl, (4-formyl-1-piperidino) carbonyl, (3-propionyl-2-piperidinyl) carbonyl, (1-butyryl-4-piperidinyl)
Carbonyl, (1-pentanoyl-4-piperidinyl)
Carbonyl, (1-hexanoyl-4-piperidinyl)
Examples of a substituent such as a carbonyl group include a piperidinylcarbonyl group which may have a linear or branched alkanoyl group having 1 to 6 carbon atoms.

The active ingredient compound (1) of the present invention can be easily produced according to a known method, for example, a method described in JP-A-3-173870.

Among the compounds (1) used as the active ingredient in the present invention, the compound having an acidic group can form a salt with a pharmacologically acceptable basic compound. Examples of such a basic compound include metal hydroxides such as sodium hydroxide, potassium hydroxide, lithium hydroxide and calcium hydroxide, alkali metal carbonates and bicarbonates such as sodium carbonate and sodium hydrogen carbonate, and sodium methylate. And alkali metal alcoholates such as potassium ethylate. Further, in the compound (1) as an active ingredient in the present invention, a compound having basicity can easily form a salt with a usual pharmacologically acceptable acid. Examples of such acids include inorganic acids such as sulfuric acid, nitric acid, hydrochloric acid, and hydrobromic acid, and organic acids such as acetic acid, p-toluenesulfonic acid, ethanesulfonic acid, oxalic acid, maleic acid, citric acid, succinic acid, and benzoic acid. Acids can be exemplified. The compound having an ammonium group in the compound (1) as an active ingredient in the present invention can be easily converted into a salt with a pharmaceutically acceptable halogen anion (chlorine anion, bromine anion, fluoride anion, iodine anion). Can be formed. These salts can also be used as the active ingredient compound in the present invention, similarly to the compound (1) in the free form. The compound (1) includes stereoisomers and optical isomers,
These can also be used as an active ingredient compound.

The active ingredient compound of the present invention represented by the above general formula (1) is effective as an oxytocin antagonist, and the antagonist is used in the form of a general pharmaceutical preparation. The preparation is prepared using a commonly used diluent or excipient such as a filler, a bulking agent, a binder, a humectant, a disintegrant, a surfactant and a lubricant. Various forms can be selected as the pharmaceutical preparation depending on the purpose of treatment, and typical examples are tablets, pills, powders, solutions, suspensions, emulsions, granules, capsules, suppositories, injections ( Liquid, suspension, etc.). In molding into tablets, various carriers well-known in the art can be widely used as carriers. Examples thereof include lactose, sucrose, sodium chloride, glucose, urea, starch, calcium carbonate, kaolin, crystalline cellulose, excipients such as silicic acid, water, ethanol, propanol, monosyrup, glucose solution, starch solution, Gelatin solution, carboxymethylcellulose, cerac, methylcellulose,
Binders such as potassium phosphate and polyvinylpyrrolidone, dried starch, sodium alginate, agar powder, laminaran powder, sodium hydrogen carbonate, calcium carbonate, polyoxyethylene sorbitan fatty acid esters, sodium lauryl sulfate, monoglyceride stearate, starch, lactose, etc. Disintegrants, sucrose, stearin, cocoa butter, disintegration inhibitors such as hydrogenated oils, quaternary ammonium bases, absorption promoters such as sodium lauryl sulfate, glycerin, humectants such as starch, starch, lactose, kaolin,
Adsorbents such as bentonite and colloidal silicic acid, and lubricating agents such as purified talc, stearate, powdered boric acid, and polyethylene glycol can be used. Further, the tablet can be made into a tablet coated with a usual coating, if necessary, for example, a sugar-coated tablet, a gelatin-encapsulated tablet, an enteric-coated tablet, a film-coated tablet or a double tablet or a multilayer tablet. In molding into the form of pills, a wide variety of carriers conventionally known in this field can be used. Examples thereof include excipients such as glucose, lactose, starch, cocoa butter, hardened vegetable oils, kaolin, talc, binders such as gum arabic, tragacanth, gelatin, ethanol, disintegrants such as laminaran, agar, etc. Can be used. In the case of molding into a suppository form, conventionally known carriers can be widely used. Examples thereof include polyethylene glycol, cocoa butter, higher alcohols, esters of higher alcohols, gelatin, and semi-synthetic glycerides.
Capsules are prepared according to a conventional method, usually by mixing the active ingredient compound with the various carriers exemplified above and filling the mixture into hard gelatin capsules, soft capsules and the like. When prepared as an injection, liquid preparations, emulsions and suspensions are preferably sterilized and isotonic with blood, and are commonly used as diluents in the art when molded into these forms. And water, ethyl alcohol, macrogol, propylene glycol, ethoxylated isostearyl alcohol, polyoxylated isostearyl alcohol, polyoxyethylene sorbitan fatty acid esters, and the like. In this case, a sufficient amount of salt, glucose or glycerin to prepare an isotonic solution may be included in the pharmaceutical preparation, and a usual solubilizer, buffer, soothing agent, etc. may be added. You may. Further, a coloring agent, a preservative, a flavor, a flavoring agent, a sweetening agent and the like and other pharmaceuticals can be contained in the pharmaceutical preparation as required.

The amount of the active ingredient compound to be contained in the oxytocin antagonist of the present invention is not particularly limited and may be appropriately selected from a wide range.
70% by weight, preferably about 5 to 50% by weight.

The administration method of the oxytocin antagonist of the present invention is not particularly limited, and is administered according to various preparation forms, the age, sex and other conditions of the patient, the degree of the disease, and the like. For example, tablets, pills, solutions, suspensions, emulsions, granules, and capsules are orally administered. In the case of an injection, it is administered alone or mixed with a normal replenisher such as glucose and amino acids, and administered intravenously.
It is administered intradermally, subcutaneously or intraperitoneally. In the case of suppositories, they are administered rectally.

The dose of the oxytocin antagonist of the present invention is appropriately selected depending on the usage, the age of the patient, gender and other conditions, the degree of the disease, etc. Usually, the amount of the active ingredient compound is about 1 kg / body weight / day. It is good to be about 0.6 to 50 mg. It is desirable that the active ingredient compound is contained in the dosage unit form in a range of about 10 to 1000 mg.

[0143]

EXAMPLES Hereinafter, in order to explain the present invention in more detail, preparation examples of the oxytocin antagonist of the present invention will be given, and then test examples of the active ingredient compound will be given.

Formulation Example 1 1- [1- (4-Dimethylaminobenzoyl) -4-piperidinyl] -3,4-dihydrocarbostyril 150 g Avicel (trade name, manufactured by Asahi Kasei Corporation) 40 g corn starch 30 g magnesium stearate 2 g hydroxypropyl Methylcellulose 10 g Polyethylene glycol-6000 3 g Castor oil 40 g Ethanol 40 g After mixing and polishing the active ingredient compound of the present invention, Avicel, corn starch and magnesium stearate, sugar coating R10 mm
Tablet with kine. The obtained tablets were treated with hydroxypropyl methylcellulose, polyethylene glycol-600.
0, coating with a film coating agent consisting of castor oil and ethanol to produce film coated tablets.

Formulation Example 2 1- [1- (2-Methoxy-4-ethoxybenzoyl) -4-piperidinyl] -3,4-dihydrocarbostyril 150 g Citric acid 1.0 g Lactose 33.5 g Dicalcium phosphate 0 g Pluronic F-68 30.0 g sodium lauryl sulfate 15.0 g polyvinyl pyrrolidone 15.0 g polyethylene glycol (Carbowax 1500) 4.5 g polyethylene glycol (Carbowax 6000) 45.0 g corn starch 30.0 g dried sodium stearate 3.0 g Dry magnesium stearate 3.0 g Ethanol appropriate amount The active ingredient compound of the present invention, citric acid, lactose, dicalcium phosphate, Pluronic F-68 and sodium lauryl sulfate are mixed.

The above mixture is sieved with a No. 60 screen and wet granulated with an alcohol solution containing polyvinylpyrrolidone, carbowax 1500 and 6000. If necessary, alcohol is added to make the powder into a pasty mass. Add corn starch and continue mixing until uniform particles are formed. The mixture was passed through a No. 10 screen, placed in a tray, and placed in an oven at 100 ° C. for 1 hour.
Dry for 2-14 hours. The dried particles are sieved through a No. 16 screen, dry sodium lauryl sulfate and dry magnesium stearate are added, mixed and compressed into the desired shape on a tablet press.

The above core is treated with varnish and talc is sprayed to prevent moisture absorption. An undercoat layer is coated around the core. Apply varnish a sufficient number of times for internal use. A further subbing layer and a smooth coating are applied to make the tablet completely round and smooth. Color coating is carried out until the desired hue is obtained. After drying, the coated tablets are polished into tablets of uniform gloss.

Formulation Example 3 7-Fluoro-1- [1- (2,4-dimethoxybenzoyl) -4-piperidinyl] -3,4-dihydrocarbostyril 5 g Polyethylene glycol (molecular weight: 4000) 0.3 g Sodium chloride 0.9 g polyoxyethylene-sorbitan monooleate 0.4 g sodium metabisulfite 0.1 g methyl-paraben 0.18 g propyl-paraben 0.02 g distilled water for injection 10.0 ml The above parabens, sodium metabisulfite and chloride The sodium is dissolved in about half of the above distilled water at 80 ° C. with stirring. The obtained solution is cooled to 40 ° C., and the active ingredient compound of the present invention, and then polyethylene glycol and polyoxyethylene sorbitan monooleate are dissolved in the above solution. Next, distilled water for injection is added to the solution to make the final volume, and the solution is sterilized by sterile filtration using an appropriate filter paper to prepare an injection.

<Pharmacological test> Oxytocin receptor binding assay Y. Chan et al. [Endocrinology, 126.2095-2].
101 (1990)], the day before DES (diethylstilbestro
Uterine muscle is excised from the rat to which l) has been injected subcutaneously, and a membrane preparation is prepared using a homogenate. This membrane sample 0.2
mg and [ ³ H] oxytocin at 100,000 dpm (1
0 ^-9 M) and 5 mM of the test compound (10 ^-9 to 10 ^-5 M).
Incubation was performed at 25 ° C. for 1 hour in a total volume of 250 μl of 100 mM Tris-HCl buffer (pH = 8.0) containing MgCl ₂ , 1 mM EDTA and 0.1% BSA. Thereafter, the mixture was filtered using a glass filter (GF / B) to separate the membrane preparation bound to [ ³ H] oxytocin, and washed twice with 5 ml of a buffer solution.
This glass filter was placed in a vial, mixed with aquasol (a cocktail for liquid scintillation), the amount of bound [ ³ H] oxytocin was measured with a liquid scintillation counter, and the inhibition rate (%) was calculated by the following equation.

Inhibition rate (%) = 100 − [(C ₁ −B) /
Except test compound; (C ₀ -B)] × 100 C _1; amount of binding ^{of [3} H] oxytocin in the film in a state where a known amount of test compound is ^[3 H] oxytocin coexist C ₀ Amount of [ ³ H] oxytocin bound to the membrane at the time of B: [in the presence of excess oxytocin (5 × 10 ⁻⁶ M)]
^[ H] oxytocin binding amount to the membrane The concentration of the test compound at which the inhibition rate calculated above was 50% was determined, and this was defined as the IC ₅₀ value. The results are shown in Tables 1 and 2 below. The test compounds are as follows.

The test compound No. 1: 1- {1- [4- (6-aminohexyloxy)
Benzoyl] -4-piperidinyl {-3,4-dihydrocarbostyril 2: 1- {1- [4- (6-acetylaminohexyloxy) benzoyl] -4-piperidinyl} -3,4-
Dihydrocarbostyril 3: 1- {1- [4- (6-methylsulfonylaminohexyloxy) benzoyl] -4-piperidinyl}-
3,4-dihydrocarbostyril 4: 1- {1- [4- (7-hydroxy-8-diethylaminooctyloxy) benzoyl] -4-piperidinyl} -3,4-dihydrocarbostyril 5: 1- {1- (4- [6- (4-methyl-1-piperazinyl) hexyloxy] benzoyl) -4-piperidinyl} -3,4-dihydrocarbostyril 6: 1- {1- (4- [6- (N-methyl -N- (2
-(2-pyridyl) ethyl) amino) hexyloxy]
Benzoyl) -4-piperidinyl {-3,4-dihydrocarbostyril 7: 1- {1- [4- (6-dimethylaminohexyloxy) benzoyl] -4-piperidinyl} -3,4-
Dihydrocarbostyril 8: 1- {1- [4- (6- (1-pyrrolidinyl) hexyloxy) benzoyl] -4-piperidinyl}-
3,4-dihydrocarbostyril 9: 1- {1- [4- (7- (1-pyrrolidyl) octyloxy) benzoyl] -4-piperidinyl} -3,
4-Dihydrocarbostyril 10: 1- {1- [4- (7- (4-Methyl-1-piperazinyl) octyloxy) benzoyl] -4-piperidinyl} -3,4-dihydrocarbostyril.

11: 1- {1- [4- (4-acetylaminobutyloxy) benzoyl] -4-piperidinyl}
-3,4-dihydrocarbostyril 12: 1- {1- [4- (6-diethylamino-5-hydroxyhexyloxy) benzoyl] -4-piperidinyl} -3,4-dihydrocarbostyril 13: 1- {1 -[4- (6-Dimethylamino-5-hydroxyhexyloxy) benzoyl] -4-piperidinyl} -3,4-dihydrocarbostyril 14: 1- {1- [4- (4- (4-benzyl-1 -Piperazinyl) butoxy) benzoyl] -4-piperidinyl} -3,4-dihydrocarbostyril 15: 1- {1- [4- (4- (1-piperazinyl) butoxy) benzoyl] -4-piperidinyl} -3, 4-
Dihydrocarbostyril 16: 1- {1- [4- [4- (1-piperazinyl) carbonyloxybutoxy] benzoyl] -4-piperidinyl-3,4-dihydrocarbostyril 17: 1- {1- [4- [ 5-hydroxy-6- (4-
Benzyl-1-piperazyl) hexyloxy] benzoyl] -4-piperidinyl} -3,4-dihydrocarbostyril 18: 1- {1- [4- (5-hydroxy-6- [N-
Methyl-N- (2-hydroxy-2-phenylethyl)
Amino] hexyloxy) benzoyl] -4-piperidinyl} -3,4-dihydrocarbostyril 19: 1- {1- [4- (6 [2 (S) -hydroxymethyl-1-pyrrolidinyl] -5-hydroxy) [Hexyloxy) benzoyl] -4-piperidinyl} -3,4-
Dihydrocarbostyril 20: 1- {1- [4- (5-hydroxy-6- (3,
4-dimethoxybenzylamino) hexyloxy) benzoyl] -4-piperidinyl} -3,4-dihydrocarbostyril.

21: 1- {1- [4- (5-hydroxy-6- (4-benzyl-1-piperidino) hexyloxy) benzoyl] -4-piperidinyl} -3,4-dihydrocarbostyril 22: 1 -{1- (4- [4- (4-Piperidinylcarbonylamino) butoxy] benzoyl) -4-piperidinyl} -3,4-dihydrocarbostyril 23: 1- {1- [4- (5-methoxy) -6-diethylmethylammoniumhexyloxy) benzoyl-4
-Piperidinyl] -3,4-dihydrocarbostyril.
Iodide 24: 1- {1- [4- (allylaminobutoxy) benzoyl] -4-piperidinyl} -3,4-dihydrocarbostyril 25: 1- {1- [4- (5-hydroxy-6- (allyl) Aminohexyloxy) benzoyl] -4-piperidinyl} -3,4-dihydrocarbostyril 26: 1- {1- [4- [3- (4-benzoyl-1-
Piperazinyl) propoxy] benzoyl] -4-piperidinyl {-3,4-dihydrocarbostyril 27: 1- [1- {4- [3- (4-anilinocarbonyl-1-piperazinyl) propoxy] benzoyl} -4
-Piperidinyl] -3,4-dihydrocarbostyril 28: 1- {1- [4- (3-phenylsulfonylaminopropoxy) benzoyl] -4-piperidinyl}-
3,4-dihydrocarbostyril 29: 1- {1- [4- (4-hydroxy-5- (1-
Pyrrolidinyl) pentyloxy) benzoyl] -4-piperidinyl} -3,4-dihydrocarbostyril 30: 1- {1- [4- (4-hydroxy-5- (1-
Piperidinyl) pentyloxy) benzoyl] -4-piperidinyl} -3,4-dihydrocarbostyril.

31: 1- {1- [4- (4-hydroxy-5- (4-morpholino) pentyloxy) benzoyl] -4-piperidinyl} -3,4-dihydrocarbostyril 32: 1- {1- [4- (3-Diethylaminopropoxy) benzoyl] -4-piperidinyl] -3,4-dihydrocarbostyril 33: 1- {1- [4- (3-hydroxy-4-diethylaminobutoxy) benzoyl] -4-piperidinyl ｝
-3,4-dihydrocarbostyril 34: 1- {1- [4-anilinooxycarbonyl]-
4-piperidinyl} -3,4-dihydrocarbostyril 35: 1- {1- [4-benzoylaminophenoxycarbonyl] -4-piperidinyl} -3,4-dihydrocarbostyril 36: 1- {1- [4- (5-Hydroxypentyloxy) benzoyl] -4-piperidinyl {-3,4-dihydrocarbostyril 37: 1- {1- [4- (4-carbamoylmethylaminocarbonylbutoxy) benzoyl] -4-piperidinyl} -3 , 4-Dihydrocarbostyril 38: 1- {1- [4- (5-carbamoyloxypentyloxy) benzoyl] -4-piperidinyl} -3,
4-dihydrocarbostyril 39: 5,7-difluoro-1- [1- (2-methoxy-4-ethoxybenzoyl) -4-piperidinyl]-
3,4-dihydrocarbostyril 40: 1- {1- [4- (5-[(1S) -1,3-dicarbamoyl] propylaminocarbonylpentyloxy) benzoyl] -4-piperidinyl} -3,4- Dihydrocarbostyril.

41: 1- [1- (2-hydroxy-4-
Ethoxybenzoyl) -4-piperidinyl] -7-fluoro-3,4-dihydrocarbostyril 42: 5-methyl-1- [1- (2-methoxy-4-ethoxybenzoyl) -4-piperidinyl] -3,4 -Dihydrocarbostyril 43: 1- {1- (4- [5- (1-imidazolyl) pentyloxy] benzoyl) -4-piperidinyl}-
3,4-dihydrocarbostyril 44: 5-methyl-1- {1- [4- (3-acetylaminopropoxy) benzoyl] -4-piperidinyl}-
3,4-dihydrocarbostyril 45: 1- {1- [4- (2-propynyloxy) benzoyl] -4-piperidinyl} -3,4-dihydrocarbostyril 46: 1- {1- [4- (4 -Carboxybutoxy) benzoyl] -4-piperidinyl {-3,4-dihydrocarbostyril 47: 1- {1- [4- (5-carbamoylpentyloxy) benzoyl] -4-piperidinyl} -3,4-dihydrocarbo Styryl 48: 1- {1- [4- (3-carbamoylpropylamino) benzoyl] -4-piperidinyl} -3,4-dihydrocarbostyril 49: 1- {1- [4- (5-hydroxypentyloxy) Benzoyl] -4-piperidinyl} -3,4-dihydrocarbostyril 50: 1- {1- [4- (5-acetylaminopentyloxy) benzo] Le] -4-piperidinyl} -3,4
Dihydrocarbostyril.

51: 1- [1- (4-methoxyanilinocarbonyl) -4-piperidinyl] -3,4-dihydrocarbostyril 52: 1- [1- (4-ethoxybenzoyl) -4-piperidinyl] carbo Styryl 53: 6,7-difluoro-1- [1- (2-methoxy-4-ethoxybenzoyl) -4-piperidinyl]-
3,4-dihydrocarbostyril 54: 1- [1- {4- [4- (1-pyrrolyl) butoxy] benzoyl} -4-piperidinyl] -3,4-dihydrocarbostyril 55: 1- [1-} 4- [3- (4-methyl-1-piperazinyl) propoxy] benzoyl} -4-piperidinyl] -3,4-dihydrocarbostyril dioxalate 56: 1- {1- [4- {5-[( 1S) -1-carbamoyl-2- (4-hydroxyphenyl)] ethylaminocarbonylpentyloxy {benzoyl] -4-piperidinyl} -3,4-dihydrocarbostyril 57: 7-fluoro-1- (1-benzoyl- 4-piperidinyl) carbostyril 58: 7-fluoro-1- [1- (2,4-dimethoxybenzoyl) -4-piperidinyl] carbostyril 59: 1- {1- [ - {5 - [(1S)-1-carbamoyl-3- (methylthio)] propyl aminocarbonyl pentyloxy} benzoyl] -4-piperidinyl}
-3,4-dihydrocarbostyril 60: 1- {1- [4- (5- (2-hydroxy-3-
Diethylaminopropoxy) pentyloxy) benzoyl] -4-piperidinyl} -3,4-dihydrocarbostyril.

61: 1- {1- [4- (5- (3-dimethylaminopropyl) aminocarbonylpentyloxy) benzoyl] -4-piperidinyl} -3,4-dihydrocarbostyril 62: 1- {1- [4- (5- (1-Pentyl-4-piperidinyl) aminocarbonylpentyloxy) benzoyl] -4-piperidinyl] -3,4-dihydrocarbostyril 63: 1- {1- [4- (5-hydroxy- 6- (1-
Pyrrolidinyl) hexyloxy) benzoyl] -4-piperidinyl {-3,4-dihydrocarbostyril 64: 1- {1- [4- (5- (4-piperidinyl) aminocarbonylpentyloxy) benzoyl] -4-piperidinyl} -3,4-dihydrocarbostyril 65: 1- {1- [4- (5- (1-pyrrolidinyl) pentyloxy) benzoyl] -4-piperidinyl}-
3,4-dihydrocarbostyril 66: 1- {1- [4- (5,6-dihydroxyhexyloxy) benzoyl] -4-piperidinyl} -3,4
-Dihydrocarbostyril 67: 1- {1- (4- [5-hydroxy-6- (3-
Methoxybenzylamino) hexyloxy] benzoyl) -4-piperidinyl} -3,4-dihydrocarbostyril 68: 1- {1- (4- [3-((1S) -1-aminoethylcarbonylamino) propoxy] benzoyl )-
4-piperidinyl} -3,4-dihydrocarbostyril 69: 5.7-dimethyl-1- [1- (2-methoxy-
4-ethoxybenzoyl) -4-piperidinyl] -3,
4-Dihydrocarbostyril 70: 1- {1- (4- [5- (2-Imidazolylsulfonyl) pentyloxy] benzoyl) -4-piperidinyl} -3,4-dihydrocarbostyril.

71: 1- {1- (4- [5-hydroxy-6- [N-methyl-N- (2- (2-pyridyl) ethyl) amino] hexyloxy] benzoyl) -4-piperidinyl}- 3,4-dihydrocarbostyril 72: 1- {1- (4- [5- (2- (4-methyl-1
-Piperazinyl) acetylamino) pentyloxy] benzoyl) -4-piperidinyl} -3,4-dihydrocarbostyril 73: 1- {1- (4- [5- (1-oxo-4-pyridylsulfonyl) pentyloxy] Benzoyl-4-piperidinyl} -3,4-dihydrocarbostyril 74: 1- {1- (4- [5- (3-hydroxy-1-
Piperidino) pentyloxy] benzoyl) -4-piperidinyl} -3,4-dihydrocarbostyril 75: 1- {1- (4- [5- (4-dimethylaminophenylsulfonyl) pentyloxy] benzoyl) -4
-Piperidinyl} -3,4-dihydrocarbostyril 76: 1- {1- [4- (5- (4-dimethylaminobenzoylamino) pentyloxy) benzoyl] -4-
Piperidinyl {-3,4-dihydrocarbostyril 77: 1- {1- (4- [5- (2- (2-hydroxyethyl) -1-piperazinyl) pentyloxy] benzoyl) -4-piperidinyl} -3, 4-dihydrocarbostyril 78: 1- {1- (4- [5- (N, N- (2-hydroxyethyl) amino] pentyloxy] benzoyl-4
-Piperidinyl} -3,4-dihydrocarbostyril 79; 1- {1- [4- (5-hydroxy-6- (1-
Piperidinyl) hexyloxy) benzoyl] -4-piperidinyl} -3,4-dihydrocarbostyril 80: 5-hydroxy-1- {1- [4- (3-acetylaminopropoxy) benzoyl] -4-piperidinyl] -3 , 4-dihydrocarbostyril.

81: 1- {1- [2-methoxy-4-
(4-carbamoylbutoxy) benzoyl] -4-piperidinyl] -3,4-dihydrocarbostyril 82: 1- {1- [4- [5- (2-methyl-1-piperidinyl) pentyloxy] benzoyl) -4 -Piperidinyl} -3,4-dihydrocarbostyril 83: 5-acetoxy-1- [1- (2-methoxy-4
-Ethoxybenzoyl) -4-piperidinyl] -3,4
-Dihydrocarbostyril 84: 1- {1- [4-[(5-isopropylamino)
[Pentyloxy] benzoyl] -4-piperidinyl}-
3,4-dihydrocarbostyril 85: 1- {1- (4- [2,4-di- (5- (1-pyrrolidinyl) pentyloxy)] benzoyl) -4-piperidinyl} -3,4-dihydrocarbo Styryl 86: 1- {1- [4- (5-dimethylaminopentyloxy) benzoyl] -4-piperidinyl} -3,4-
Dihydrocarbostyril 87: 1- {1- [2-methoxy-4- (4-thiomorpholinocarbonylbutyloxy) benzoyl] -4-piperidinyl} -3,4-dihydrocarbostyril 88: 1- {1- (2 -Methoxy-4- [4- (1-oxo-4-thiomorpholino) carbonylbutyloxybenzoyl] -4-piperidinyl} -3,4-dihydrocarbostyril 89: 1- {1- (2-methoxy-4-) [1,1-Dioxo-4-thiomorpholino) carbonylbutyloxybenzoyl) -4-piperidinyl} -3,4-dihydrocarbostyril 90: 1- {1- [4- (5-tert-butylaminopentyloxy) Benzoyl] -4-piperidinyl}-
3,4-dihydrocarbostyril.

91: 1- {1- [4- (5- (2-propynylamino) pentyloxy) benzoyl] -4-piperidinyl} -3,4-dihydrocarbostyril 92: 1- {1- [4- (6-Hydroxy-7-diethylamino) heptyloxy) benzoyl] -4-piperidinyl} -3,4-dihydrocarbostyril 93: 1- {1- [4- (5-cyclopropylaminopentyloxy) benzoyl] -4 -Piperidinyl｝-
3,4-dihydrocarbostyril 94: 1- {1- [4- (5-tricyclo [3.3.
1.1] Decanylmethylaminopentyloxy) benzoyl] -4-piperidinyl} -3,4-dihydrocarbostyril 95: 1- {1- [5- [3- (3-azaspiro (5,
5) Undecanyl)]-(5-phenylspiro-4-
(1-piperidinyl) pentyloxy) benzoyl]-
4-piperidinyl {-3,4-dihydrocarbostyril 96: 1- {1- [4- (5-butylaminopentyloxy) benzoyl] -4-piperidinyl} -3,4-dihydrocarbostyril 97: 1- { 1- [4- (5-cyclohexylaminopentyloxy) benzoyl] -4-piperidinyl}-
3,4-dihydrocarbostyril 98: 1- {1- [4- (5-tricyclo [3.3.
1.1] Decanylaminopentyloxy) benzoyl]
-4-piperidinyl} -3,4-dihydrocarbostyril 99: 1- {1- [4- (3-acetylaminopropoxy) benzoyl] -4-piperidinyl} -3,4-dihydrocarbostyril

[0161]

[Table 1]

[0162]

[Table 2]

────────────────────────────────────────────────── ─── Continued on the front page (51) Int.Cl. ⁶ Identification code FI A61K 31/535 A61K 31/535 // C07D 215/22 C07D 215/22 401/04 211 401/04 211 401/14 401/14 (72) Inventor Kenji Nakaya 48 Kamibetsu-gu Kita, Kawauchi-cho, Tokushima, Tokushima (72) Michiaki Tominaga 310-6, Takaiso, Kamiita-cho, Itano-gun, Tokushima (72) Inventor Yoichi Yabuuchi 900, Omatsu, Kawauchi-cho, Tokushima, Tokushima JP-A-3-173870 (JP, A) JP-A-63-26893 (JP, A) JP-A-60-54326 (JP, A) JP-A-58-222060 (JP, A) JP-A-56-150050 (JP, A) (58) Fields investigated (Int. Cl. ⁶ , DB name) C07D 215/22 C07D 401/04 C07D 401/14 CA (STN) REGISTRY (STN)

Claims (2)

(57) [Claims] 1. A compound of the general formula [Wherein R ¹ is selected from a hydrogen atom, a nitro group, a lower alkoxy group, a lower alkoxycarbonyl group, a lower alkyl group, a halogen atom, a lower alkanoyl group, a lower alkyl group, a benzoyl group and a phenyl lower alkoxycarbonyl group as a substituent. An amino group, a hydroxyl group, a cyano group, a carboxy group, a lower alkanoyloxy group or a hydrazinocarbonyl group which may have 1 to 2 groups.
q shows the integer of 1-3. R is a group Is shown. R ² is a hydrogen atom, a lower alkoxycarbonyl group; a lower alkanoyl group as a substituent on a phenyl ring,
A phenoxycarbonyl group which may have 1 to 2 groups selected from the group consisting of a lower alkyl group and a benzoyl group; and a phenoxycarbonyl group which may have 1 to 3 groups selected from the group consisting of a nitro group; phenyl lower alkenyl A phenyl lower alkanoyl group which may have an amino group which may have a lower alkoxycarbonyl group as a substituent on the lower alkanoyl group; an alkanoyl group; an alkenylcarbonyl group; a lower alkoxy group as a substituent on the phenyl ring. A phenylsulfonyl group which may have; a group -CONR ⁸ R ⁹ (wherein R ⁸ and R ⁹ are the same or different and are a hydrogen atom or a lower alkoxy group, a lower alkyl group, a halogen atom, A group selected from the group consisting of a lower alkyl group and a lower alkanoyl group as a substituent; A phenyl group which may have 1 to 3 groups selected from the group consisting of an amino group and a nitro group which may have 2 to 2 groups; a heterocyclic carbonyl group (the heterocyclic ring has a phenyl lower group as a substituent; (It may have 1 to 3 groups selected from the group consisting of an alkoxycarbonyl group, a phenyl lower alkoxy group, an oxo group, a lower alkyl group and a lower alkylenedioxy group). A naphthylcarbonyl group; a thienyl lower alkanoyl group; a tricyclo [3.3.1.1] decanyl lower alkanoyl group; a tricyclo [3.3.1.1] decanylcarbonyl group; or a group (P represents 0 or an integer of 1 to 3. R ¹³ is a hydroxyl group; an alkoxy group; a hydroxyl group, a lower alkanoyloxy group, a tri-lower alkylammonium group, a lower alkoxy group and a group —NR ¹⁴ R ¹⁵ (R ¹⁴ and R ¹⁵ are the same or different,
Hydrogen atom, lower alkyl group, hydroxyl-substituted lower alkyl group, lower alkanoyl group, tetrahydropyranyl lower alkyl group, phenyl group, may have a hydroxyl group on the lower alkyl group, and a lower alkoxy group as a substituent on the phenyl ring A phenyl lower alkyl group or a pyridyl lower alkyl group which may have R ¹⁴ and R
¹⁵ may be bonded to each other via a nitrogen atom, an oxygen atom or a sulfur atom together with or without a nitrogen atom to which they are bonded to form a 5- to 6-membered saturated heterocyclic ring. The heterocyclic ring may have a substituent selected from the group consisting of a carbamoyl group, a lower alkyl group, a phenyl lower alkyl group, a phenyl group and a hydroxyl-substituted lower alkyl group. A) an alkoxy group having 1 or 2 groups selected from the group consisting of: a carboxy group-substituted alkoxy group; a halogen-substituted lower alkoxy group; a lower alkoxycarbonyl group-substituted alkoxy group; a lower alkanoyloxy group-substituted lower alkoxy group; a lower alkenyloxy group A lower alkoxy group substituted with a lower alkoxy group; a lower alkoxy group substituted with a lower alkylsulfonyloxy group; a lower alkoxy group substituted with a benzoyloxy group; a tricyclo [3.
3.1.1] decanyl-substituted lower alkoxy group; a lower alkoxy lower alkoxy group having one or two groups selected from the group consisting of a hydroxyl group and an amino group which may have a lower alkyl group as a substituent; A morpholinyl-substituted lower alkoxy group which may have a group selected from the group consisting of an alkyl group and an oxo group; a benzimidazolylthio-substituted lower alkoxy group; a benzimidazolylsulfinyl-substituted lower alkoxy group; a group -OA- (E) l
-NR ⁴ R ⁵ (A represents an alkylene group; 1 is 0 or 1
Indicates an integer. E represents a group -CO- or a group -OCO-. R ⁴ and R ⁵ are the same or different and each represent a hydrogen atom, a lower alkyl group which may have a hydroxyl group or a cyano group as a substituent, a lower alkenyl group, a lower alkynyl group, a phenyl lower alkyl group, and a halogen atom as a substituent. 1
A lower alkanoyl group which may have 1 to 3 amino groups which may have 1 to 2 groups selected from a lower alkyl group, a lower alkanoyl group and a phenyl lower alkoxycarbonyl group as a substituent on the phenyl ring; A benzoyl group, a phenyl group, a lower alkoxycarbonyl group which may have a group selected from the group consisting of a nitro group, and an amino group which may have a phenyl lower alkoxycarbonyl group as a substituent on a lower alkyl group; A lower alkoxycarbonyl lower alkyl group, an amide group which may have a lower alkyl group as a substituent, a pyrrolidinylcarbonyl group which may have a phenyl lower alkoxycarbonyl group as a substituent on a pyrrolidine ring, a lower alkanoyl group Phenyl lower alkyl as a substituent Alkoxycarbonylamino group, a hydroxyl group,
It may have a phenyl group, a carbamoyl group, an imidazolyl group or a lower alkylthio group which may have a hydroxyl group as a substituent on the phenyl ring, and may have a hydroxyl group as a substituent as a substituent on an amino group. An alkyl group, a lower alkenyl group, an amino lower alkanoyl group having a phenyl lower alkyl group, a lower alkylsulfonyl group, a lower alkanoyl group or a phenyl lower alkoxycarbonyl group which may have a lower alkoxy group as a substituent on a phenyl ring; A hydroxyl-substituted lower alkanoyl group, a lower alkanoyloxy lower alkanoyl group, a lower alkylsulfonyl group, a group selected from the group consisting of a lower alkyl group, a nitro group, and a lower alkyl group and a lower alkanoyl group as a substituent on a phenyl ring; Up to 2 A phenylsulfonyl group which may have a group selected from the group of amino groups which may be present, a phenyl group which may have a hydroxyl group as a substituent on a phenyl ring as a substituent on a lower alkyl group, an imidazolyl group, carbamoyl May have a group or a lower alkylthio group, or an amide lower alkyl group which may have a lower alkyl group as a substituent on the amide group, a group selected from the group consisting of a lower alkyl group and a lower alkanoyl group as a substituent. Amino lower alkyl group which may have, anilinocarbonyl group, piperidinyl group which may have phenyl lower alkyl group as a substituent, cycloalkyl group, cycloalkenylcarbonyl group, hydroxyl group and lower alkanoyl as a substituent on the cycloalkyl group Groups selected from the group consisting of oxy groups are 1 to A cycloalkylcarbonyl group, a tetrahydropyranyl lower alkyl group having 1 to 4 groups selected from the group consisting of a hydroxyl group and a lower alkoxy group as a substituent on a tetrahydropyranyl ring, a pyrrolidinyl, a piperazinyl , A lower alkanoyl group having a 5- to 6-membered saturated heterocyclic ring selected from the group consisting of piperidinyl and morpholinyl groups (the heterocyclic ring has a substituent selected from the group consisting of a lower alkyl group and a phenyl group). ),
It represents a piperidinylcarbonyl group, a lower alkanoyloxy lower alkyl group, a pyridyl lower alkyl group which may have a lower alkanoyl group as a substituent, or an amino acid residue capable of forming an amide group with an amino group bonded thereto.
R ⁴ and R ⁵ are bonded together with or without a nitrogen atom, an oxygen atom or a sulfur atom together with the nitrogen atom to which they are bonded to form a 5- or 6-membered saturated or unsaturated heterocyclic ring. You may. The heterocyclic group may be a phenyl group, an oxo group, a hydroxyl group, a lower alkenyl group, which may have a substituent selected from the group consisting of a lower alkoxy group and a halogen atom on the phenyl ring as a substituent.
Carboxy group, phenyl lower alkyl group which may have a hydroxyl group on the lower alkyl group, lower alkanoyl group,
A lower alkyl group which may have a hydroxyl group as a substituent, a benzoyl group, an amide group which may have a lower alkyl group as a substituent, an anilinocarbonyl group, a benzoyl lower alkyl group, a lower alkylsulfonyl group, a piperidinyl group, a pyrimidyl group , A pyridyl group and a lower alkoxycarbonyl group. Lower carboxamoyloxy group-substituted lower alkoxy group; lower alkylthio-substituted lower alkoxy group; lower alkylsulfonyl-substituted lower alkoxy group; lower alkylsulfinyl-substituted lower alkoxy group; alkenyloxy group; phenoxy group; lower alkanoyloxy group; lower alkylsulfonyloxy group A lower alkynyloxy group;
Phenyl-lower alkoxy group; a cycloalkyl group; a cycloalkyl group; a cycloalkenyl group; imidazo [4,5-c] pyridylcarbonyl lower alkoxy group; group ^{- (B) lNR 6 R 7} (l is as .B the It is a lower alkylene group or a group -CO- .R ⁶ and R ⁷
Are the same or different and are a hydrogen atom, a lower alkyl group, a lower alkanoyl group which may have 1 to 3 halogen atoms as a substituent, a carboxy lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyl lower alkyl group, a lower It represents an alkenyl group, an amide lower alkyl group or a phenyl lower alkoxycarbonyl group which may have a lower alkyl group as a substituent. Also this R
⁶ and R ⁷ together with the nitrogen atom to which they are attached, a nitrogen atom, may form a saturated or unsaturated heterocyclic 5-6 membered ring bonded to each other without or via an oxygen atom or a sulfur atom. The heterocyclic ring may have a lower alkoxycarbonyl group, a lower alkyl group, a lower alkylthio group or an oxo group as a substituent. A nitro group; a halogen atom; a lower alkylsulfonyl group; a lower alkyl group which may have 1 to 3 groups selected from a halogen atom, a hydroxyl group, a phenyl group and a lower alkoxy group as a substituent; An alkoxy group; an oxiranyl-substituted lower alkoxy group; a phthalimide-substituted alkoxy group; an amidino-substituted lower alkoxy group; a pyrrolyl-substituted lower alkoxy group; a cyano group; a lower alkoxycarbonyl group; an amidino group; a carbamoyl group; Lower alkoxycarbonyl lower alkyl group; carboxy lower alkyl group; lower alkoxy lower alkyl group; lower alkanoyloxy lower alkyl group; hydroxyimino lower alkyl group; phenyl group; lower alkylthio group; A lower alkenyl group which may have a hydroxyl group as a substituent; a lower alkylenedioxy group; a lower alkylsilyl group; a pyrimidylthio lower alkoxy group; a pyrimidylsulfinyl lower alkoxy group; a pyrimidylsulfonyl lower alkoxy group; An imidazolylthio lower alkoxy group which may have a lower alkyl group; an imidazolylsulfonyl lower alkoxy group which may have a lower alkyl group as a substituent; a group selected from the group consisting of a lower alkyl group, a lower alkenyl group and an oxo group; An ammonium lower alkoxy group having a phenylthio lower alkoxy group which may have a substituent selected from the group consisting of a nitro group and an amino group on the phenyl ring;
The phenyl ring may have a nitro group as a substituent and a group selected from an amino group which may have one or two groups selected from a lower alkanoyl group and a lower alkyl group as a substituent. A phenylsulfonyl lower alkoxy group; a pyridylthio lower alkoxy group or a pyridylsulfonyl lower alkoxy group which may have an oxo group on a pyridine ring. ) N is an integer of 1 or 2,
m represents 0 or an integer of 1 to 3, respectively. R ³ represents a lower alkyl group. R ¹⁰ represents a group — (CO) lNR ¹¹ R ¹² (l
Is the same as above. R ¹¹ and R ¹² are the same or different and are a hydrogen atom, a lower alkyl group, a phenyl lower alkyl group, a lower alkenyl group, a benzoyl group which may have a lower alkoxy group on the phenyl ring, a tricyclo [3.3.1.
1] A decanyl group, a phenyl group or a cycloalkyl group which may have a lower alkoxy group on a phenyl ring. R ¹¹ and R ¹² may be bonded to each other via a nitrogen atom, an oxygen atom or a sulfur atom together with or without a nitrogen atom to which they are bonded to form a saturated or unsaturated heterocyclic ring. The heterocyclic ring may be a benzoyl group, a lower alkanoyl group, a phenyl lower alkyl group or a phenyl group which may have a substituent selected from the group consisting of a lower alkoxy group and a lower alkanoyl group on the phenyl ring. It may have a group selected from the group consisting of: ). The bond at the 3- or 4-position of the carbostyril skeleton represents a single bond or a double bond. However, when R ¹ is a hydrogen atom and ^{1 in the} group — (CO) 1 —NR ¹¹ R ¹² is 0, R ¹¹ and R ¹² must not be hydrogen atoms at the same time. An oxytocin antagonist comprising, as an active ingredient, a carbostyril derivative represented by the formula: 2. The method according to claim 1, wherein the active ingredient is 1- {1- [4- (3-acetate).
Tylaminopropoxy) benzoyl] -4-piperidini
Di-3,4-dihydrocarbostyril or a salt thereof;
1- [1- {4- [5- (1-pyrrolidinyl) pentyl]
[Oxy] benzoyl} -4-piperidinyl] -3,4-
Selected from the group consisting of dihydrocarbostyril or a salt thereof
2. The oxytoshi according to claim 1, which is at least one selected from the group consisting of:
Antagonists.