JP4787529B2 - Pharmaceutical composition - Google Patents

Description

  The present invention relates to pharmaceutical compositions.

Among the acid-fast bacilli, Mycobacterium tuberculosis ( Mycobacterium tuberculosis ) is widely known and is said to be infected with one third of the human race. Also, Mycobacterium africanum and Mycobacterium bovis are known as a tuberculosis group similar to Mycobacterium tuberculosis and known as mycobacteria having strong pathogenicity to humans.

  These tuberculosis diseases are treated with three drugs of rifampicin, isoniazid and ethambutol (or streptomycin), which are positioned as first-line drugs, or four drugs with pyrazinamide added thereto.

  However, because the treatment of tuberculosis requires a very long-term medication, compliance is poor and treatment failure is not uncommon.

  In addition, rifampicin causes liver damage, full syndrome, drug allergy, concomitant contraindication with other agents induced by P450-related enzymes, isoniazid causes peripheral neuropathy, combined with rifampicin causes severe liver damage, and causes ethambutol There have been reports of side effects such as visual acuity loss due to optic neuropathy, reduced hearing due to streptomycin 8th neuropathy, hepatic damage with pyrazinamide, gout attack associated with elevated uric acid levels, vomiting etc. (A Clinician's Guide To Tuberculosis, Michael D. Iseman 2000 by Lippincott Williams & Wilkins, printed in the USA, ISBN 0-7817-1749-3, Tuberculosis second edition, Fumiyuki Kuze, Takahide Izumi, School of Medicine 1992).

  In fact, it is reported that 70% of the cases (about 23%, 52 cases) of the whole (total inpatients surveyed: 228 cases) can not be administered standard chemotherapy due to these side effects. There are also (Kekkaku Vol. 74: 77-82, 1999).

  Hepatotoxicity common to rifampicin, isoniazid and pyrazinamide among the five drugs used in combination in the first line is particularly known as the most frequent side effect. On the other hand, tuberculosis bacteria that are resistant to anti-tuberculosis agents and tuberculosis bacteria that have become multidrug resistant are increasing, making treatment even more difficult.

  According to the WHO survey (1996-1999), among the tuberculosis bacteria isolated in the world, the proportion showing resistance to any of the existing antituberculosis agents reaches 19%, and also multi-drug resistant tuberculosis bacteria5. It is announced that 1%. Carriers infected with such multidrug-resistant tuberculosis bacteria are said to reach 60 million people worldwide, and there is concern about the increase of multidrug-resistant tuberculosis bacteria in the future (April 2001 as a supplement to the journal Tuberculosis, "Scientific Blueprint for TB Drug Development".

  Furthermore, it is reported that the majority of deaths of AIDS patients are caused by tuberculosis, and as of 1997, the number of persons infected with tuberculosis and HIV has reached 10.7 million (Global Alliance for TB drug development) ). It is also believed that mixed infections are associated with a risk of developing tuberculosis at least 30 times higher than usual.

  Based on such current conditions, as a profile of the desired antituberculosis drug, (1) effective for multidrug-resistant tuberculosis, (2) capable of short-term chemotherapy, (3) having few side effects, (4) Those showing efficacy against latently infected Mycobacterium tuberculosis (Latent Mycobacterium tuberculosis), and (5) Those that can be orally administered.

In addition, Mycobacterium avium and Mycobacterium intracellulare cause is the bacteria in recent years increased to have that MAC disease (Mycobacterium avium-intracellulare complex disease) In addition, other Mycobacterium kansasii, Mycobacterium marinum, Mycobacterium simiae , Mycobacterium scrofulaceum, Mycobacterium szulgai, Mycobacterium xenopi, Mycobacterium Atypical anti-acidic bacteria such as malmoense , Mycobacterium haemophilum , Mycobacterium ulcerans , Mycobacterium shimoidei , Mycobacterium fortuitum , Mycobacterium chelonae , Mycobacterium smegmatis , Mycobacterium aurum, etc. are known as pathogenic bacteria to have human pathogenic bacteria.

  Today, there are few promising therapeutic agents for these atypical mycobacterial diseases, and the antituberculous agents rifampicin, isoniazid, ethambutol, streptomycin, kanamycin, general bacterial infections treatment agents new quinolone agents, macrolide antibiotics At present, agents, aminoglycoside type antibacterial agents and tetracycline type antibacterial agents are used in combination.

  However, in the treatment of atypical acid-fast bacilliosis, long-term medication is required, and cases that become incurable and die as compared to infections caused by general bacteria have been reported. In order to solve such current situation, development of a drug showing stronger efficacy is desired.

  For example, 6-nitro-1,2,3,4-tetrahydro [2,1-b] imidazopyran compounds are disclosed in Japanese Patent Application Laid-Open No. 11-508270 (WO 97/01562, Patent Document 1) in vitro. (H37Rv strain) and bactericidal activity against multidrug-resistant Mycobacterium tuberculosis and having therapeutic effect by oral administration to a tuberculosis-infected animal model, it is useful as an antituberculosis agent Is disclosed.

  However, the compounds described in the above documents differ from the compounds of the present invention in basic skeleton and are dissimilar compounds.

  Furthermore, Kupswamynagarajan et al., European Journal of Medicinal Chemistry, 1989, Vol. 24, pp. 631 to 633 (European Journal of Medicinal Chemistry 1989, Vol. 24, p. 631-633) (non- Patent Document 1) describes the general formula (I)

In which R ¹ represents a hydrogen atom or a methyl group, and-(CH ₂ ) _n R ² represents a chloromethyl group, a C1 to C7 alkyl group, an isopropoxymethyl group, a 3-propenyloxymethyl group, and an unsubstituted phenoxymethyl group. Group compounds and compounds in which R ¹ and-(CH ₂ ) _n R ² are combined to form a cyclopentane ring or cyclohexane ring (total of 16 types of compounds) have a bactericidal action against Mycobacterium tuberculosis (H37Rv strain) Is reported to have.

However, the above references, the active compounds by oral administration is only slightly four high compounds the most active among them, the R ¹ that is, in the general formula (I) represents a hydrogen atom, - (CH ₂ It has been described that the mutagenicity was found in a compound (CGI-17341) in which _n R ² is ethyl, and therefore the development of these series of compound groups as a drug was abandoned.

Furthermore, in Anti-microvial Agent and Chemotherapy, February 1993, pp. 183-186 (Dilip R. Astekar et. Al., Antimicrobial Agents and Chemotherapy, Feb. 1993, p 183-186) (Non-patent Document 2). Has the bactericidal activity against the above-mentioned CGI-17341 antibacterial profile, ie, against M. tuberculosis (H37Rv strain) and multidrug-resistant M. tuberculosis, but the atypical acid-fast bacillus M. avium , M. intracellulare And M. fortuitum are reported to have no activity at 250 μg / ml or less.
WO 97/01562 European Journal of Medicinal Chemistry, 1989, 24: 631-633 Anti-Micro Vial Agent and Chemotherapy, February 1993, pages 183-186

  An object of the present invention is to provide a pharmaceutical composition having excellent bactericidal activity against Mycobacterium tuberculosis and multidrug-resistant Mycobacterium tuberculosis.

  An object of the present invention is to provide a pharmaceutical composition having excellent bactericidal activity against atypical acid-fast bacteria.

  As a result of intensive studies to solve the above problems, the present inventor has found that 2,3-dihydroimidazo [2] having excellent bactericidal activity against Mycobacterium tuberculosis, multidrug-resistant Mycobacterium tuberculosis and atypical acid-fast bacteria. , 1-b] Oxazole compounds were successfully synthesized. The present invention has been completed based on such findings.

  The present invention provides the pharmaceutical compositions shown in the following 1 to 3.

  1. General formula (1)

At least one selected from the group consisting of 2,3-dihydro-6-nitroimidazo [2,1-b] oxazole compounds represented by the formula (IV), their optically active substances, and their pharmacologically acceptable salts Pharmaceutical composition containing.
[In formula, R < ¹ > shows a hydrogen atom or a C1-6 alkyl group. n shows the integer of 0-6. R ² represents a group of any of the following formulas (A) to (G) and (a) to (y). In addition, R ¹ and-(CH ₂ ) _n R ² may be combined with adjacent carbon atoms via a nitrogen atom to form a spiro ring represented by the following general formula (H).

The group represented by formula (A):
-OR ³ (A)
(Wherein R ³ is
A1) hydrogen atom;
A2) C1-6 alkyl group;
A3) C1-6 alkoxy-C1-6 alkyl group;
A4) phenyl C1-6 alkyl group (on the phenyl ring, phenyl C1-6 alkoxy group; halogen substituted or unsubstituted C1-6 alkyl group; halogen substituted or unsubstituted C1-6 alkoxy group and phenoxy group [phenyl And at least one group selected from the group consisting of halogen-substituted or unsubstituted C1-6 alkoxy groups may be substituted on the ring);
A5) biphenylyl C1-6 alkyl group;
A6) phenyl C2-6 alkenyl group;
A7) C1-6 alkylsulfonyl group;
A8) a benzenesulfonyl group which may be substituted by a C1-6 alkyl group;
A9) C1-6 alkanoyl;
A10) A group represented by formula (Aa):

(Wherein R ⁴ represents a C1-6 alkoxycarbonyl group; a phenyl C1-6 alkoxycarbonyl group [wherein a phenyl C1-6 alkoxy group, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted At least one group selected from the group consisting of unsubstituted C1-6 alkoxy groups may be substituted or phenyl C1-6 alkyl group [on phenyl ring, phenyl C1-6 alkoxy group, halogen At least one selected from the group consisting of a substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted).
A11) biphenylyl C1-6 alkoxycarbonyl group;
A12) benzoxazolyl C1-6 alkyl group (wherein at least one oxo group may be substituted on the benzoxazole ring);
A13) benzoxazolyl group;
Or
A14) Oxazolyl C1-6 alkyl group (On the oxazole ring, at least one of a group selected from the group consisting of a phenyl group and a C1-6 alkyl group may be substituted)
Indicates )

The group represented by formula (B):
-SR ⁵ (B)
(Wherein, R ⁵ represents a tetrazolyl group [a phenyl group which may have a C 1 to ⁶ alkyl group or a halogen atom may be substituted on the tetrazole ring] or a benzoxazolyl group)

The group represented by formula (C):
-COOR ⁶ (C)
(Wherein, R ⁶ represents a C1 to ⁶ alkyl group)

The carbamoyloxy group represented by formula (D):
-OOCNR ⁷ R ⁸ (D)
(Wherein, R ⁷ and R ⁸ are the same or different,
D1) Hydrogen atom;
D2) C1-8 alkyl;
D3) halogen substituted C1-6 alkyl group;
D4) C1-6 alkoxycarbonyl-C1-6 alkyl group;
D5) C3-8 cycloalkyl group;
D6) phenyl C1-6 alkyl group (on the phenyl ring, a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group At least one may be substituted);
D7) phenyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group, a halogen substituted or unsubstituted C1-6 alkoxy group, a C1-6 alkanoyl group, a carboxyl group, C1-6 A group selected from the group consisting of alkoxycarbonyl group, phenyl C1-6 alkoxycarbonyl group, carbamoyl group, C1-6 alkyl carbamoyl group, aminosulfonyl group and morpholino group may be substituted by 1 to 3);
D8) Naphthyl;
Or
D9) Shows a pyridyl group.
D10) R ⁷ and R ⁸ together with the nitrogen atom to which they are adjacent are bonded to each other via or without another heteroatom or carbon atom to form a saturated complex as shown in (D10-1) to (D10-3) below A ring group or a benzene-fused heterocyclic group shown in the following (D10-4) to (D10-7) may be formed. )
(D10-1) Piperazinyl group represented by the general formula (Da):

(Where R ⁹ is
(Da1) hydrogen atom;
(Da2) C1-6 alkyl group;
(Da3) phenyl C1-6 alkyl group (a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group on the phenyl ring At least one of which may be substituted);
(Da4) phenyl group (on the phenyl ring, at least one group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group, and a halogen substituted or unsubstituted C1-6 alkoxy group May be substituted);
(Da5) C1-6 alkoxycarbonyl group;
(Da6) phenyl C1-6 alkoxycarbonyl group (on the phenyl ring, selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group At least one of the groups may be substituted);
(Da7) phenyl C3-6 alkenyloxycarbonyl group (in the phenyl ring, at least one halogen-substituted or unsubstituted C1-6 alkyl group may be substituted);
Or
(Da8) phenyl C1-6 alkylidene substituted amino group (a halogen-substituted or unsubstituted C1-6 alkyl group may be substituted at least one on the phenyl ring)
Indicates );
(D10-2) A group represented by formula (Db):

(Wherein, the dotted line indicates that it may be a double bond. R ¹⁰ represents
(Db1) hydrogen atom;
(Db2) phenyl group (in the phenyl ring, at least one group selected from the group consisting of halogen, halogen-substituted or unsubstituted C1-6 alkyl group and halogen-substituted or unsubstituted C1-6 alkoxy group is May be substituted);
(Db3) phenoxy group (on the phenyl ring, at least one halogen-substituted or unsubstituted C1-6 alkyl group may be substituted);
Or
(Db4) phenylamino group (on the phenyl ring, at least one halogen-substituted or unsubstituted C1-6 alkyl group may be substituted)
Indicates );
(D10-3) morpholino group;
(D10-4) indolinyl group (on the indoline ring, at least one halogen atom may be substituted);
(D10-5) isoindolinyl group (on the isoindoline ring, at least one halogen atom may be substituted);
(D10-6) 1,2,3,4-tetrahydroquinolyl group (on the 1,2,3,4-tetrahydroquinoline ring, at least one halogen atom may be substituted);
Or
(D10-7) 1,2,3,4-Tetrahydroisoquinolinyl group (at least one halogen atom may be substituted on the 1,2,3,4-tetrahydroisoquinoline ring)

The phenoxy group represented by formula (E):

[Wherein, X represents a halogen atom or an amino-substituted C1-6 alkyl group which may have a C1-6 alkyl group as a substituent. m shows the integer of 0-3. R ¹¹ is
E1) hydrogen atom;
E2) halogen-substituted or unsubstituted C1-6 alkyl group;
E3) halogen-substituted or unsubstituted C1-6 alkoxy group;
E4) A group represented by formula (Ea):
-(W) o-NR ¹² R ¹³ (Ea)
(Wherein, W represents a group -CO- or a C1-6 alkylene group, o represents 0 or 1. R ¹² and R ¹³ are the same or different,
(Ea1) hydrogen atom;
(Ea2) C1-6 alkyl group;
(Ea3) C1-6 alkanoyl group;
(Ea4) C1-6 alkoxycarbonyl group;
(Ea5) phenyl C1-6 alkyl group (a halogen atom on a phenyl ring; halogen substituted or unsubstituted C1-6 alkyl group; halogen substituted or unsubstituted C1-6 alkoxy group and phenoxy group [phenyl ring Is optionally substituted by at least one group selected from the group consisting of halogen atoms, halogen-substituted or unsubstituted C1-6 alkyl groups and halogen-substituted or unsubstituted C1-6 alkoxy groups as substituents And at least one member selected from the group consisting of (1) may be substituted, and a C1 to 6 alkoxyimino group may be substituted on the C1 to 6 alkyl moiety);
(Ea6) phenyl group (at least one group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group on a phenyl ring May be substituted);
(Ea7) Benzoyl group (in the phenyl ring, at least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group is May be substituted);
(Ea8) a pyridyl group (on the pyridine ring, at least one halogen atom may be substituted);
(Ea9) phenyl C1-6 alkyl group (in the phenyl ring, a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group At least one may be substituted);
(Ea10) phenoxy C1-6 alkyl group (on the phenyl ring, a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group At least one may be substituted);
Or
(Ea11) benzoyl C1-6 alkyl group (on the phenyl ring, a group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group At least one may be substituted)
Indicates );
E5) imidazolyl;
E6) triazolyl group;
E7) morpholino group;
E8) thiomorpholino group;
E9) s-Oxidothiomorpholino group;
E10) Piperidyl group represented by the general formula (Eaa):

(Wherein, W and o are the same as above. R ^14A represents a hydrogen atom, a hydroxyl group, a C1-6 alkoxy group or a phenyl group [a halogen atom may be substituted on the phenyl ring]). The dotted line shows that it may be a double bond, and when the dotted line shows a double bond, it is assumed that only R ¹⁴ is substituted R ¹⁴ and R ^{14 A} together with their adjacent carbon atoms good .R ¹⁴ be formed C1~4 alkylenedioxy group bonded to each other,
(Eaa1) hydrogen atom;
(Eaa2) C1-6 alkoxycarbonyl group;
(Eaa3) phenoxy group (a halogen atom on a phenyl ring; halogen substituted or unsubstituted C1-6 alkyl group; halogen substituted or unsubstituted C1-6 alkoxy group; C1 to 4 alkylenedioxy group; C1 to 6 Alkoxycarbonyl group; cyano group; C2-6 alkenyl group; nitro group; phenyl group; having a group selected from the group consisting of phenyl group, C1-6 alkyl group, carbamoyl group and C1-6 alkanoyl group as a substituent C1-6 alkanoyl substituted C1-6 alkyl group; hydroxyl group; C1-6 alkoxycarbonyl substituted C1-6 alkyl group; phenyl C1-6 alkyl group; C1-6 alkanoyl group; C1-6 alkylthio group; 2,4-triazolyl group; isoxazolyl group; imidazolyl group; benzothiazolyl group; H-benzotriazolyl group; pyrrolyl group; benzoxazolyl group; piperazinyl group [C1-6 alkoxycarbonyl group as a substituent, and phenyl C1-6 alkyl group (on phenyl ring as a substituent (halogen on a phenyl ring At least one group selected from the group consisting of an atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted At least one kind of the above-mentioned groups may be substituted); piperidyl group [in the piperidine ring, at least one amino group may be substituted. 6 alkyl group and phenyl group (on the phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C 6) at least one group selected from the group consisting of alkoxy groups may be substituted), and at least one group selected from the group consisting of) may be substituted] and a carbamoyl group At least one of the selected groups may be substituted);
(Eaa4) hydroxyl group;
(Eaa5) carboxy group;
(Eaa6) phenyl group (a phenyl group, a phenoxy group as a substituent [a phenyl atom as a substituent, a halogen atom as a substituent, a halogen substituted or unsubstituted C1-6 alkyl group, and a halogen substituted or unsubstituted C1 At least one group selected from the group consisting of 6 alkoxy groups may be substituted], a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group And at least one of the groups selected from the group consisting of
(Eaa7) C1-6 alkoxy group;
(Eaa8) C3-8 cycloalkyl-C1-6 alkoxy group;
(Eaa9) phenylcarbamoyl group (in which at least one of a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group on a phenyl ring Species may be substituted);
(Eaa10) tetrahydropyranyloxy group;
(Eaa11) 1,3-dioxolanyl group;
(Eaa12) oxo group;
(Eaa13) a naphthyloxy group (on the naphthalene ring, at least one C1-6 alkyl group may be substituted);
(Eaa14) 2,3-dihydrobenzofuryloxy group (even if at least one group selected from the group consisting of a C1-6 alkyl group and an oxo group is substituted on the 2,3-dihydrobenzofuran ring Good);
(Eaa15) a benzothiazolyloxy group (on the benzothiazole ring, at least one C1-6 alkyl group may be substituted);
(Eaa16) 1,2,3,4-tetrahydronaphthyloxy group (in the 1,2,3,4-tetrahydronaphthalene ring, at least one oxo group may be substituted);
(Eaa17) 1,3-benzooxathiolanyloxy group (in the 1,3-benzooxathiolane ring, at least one oxo group may be substituted);
(Eaa 18) isoquinolyloxy group;
(Eaa19) pyridyloxy group;
(Eaa20) quinolyloxy group (on the quinoline ring, at least one C1-6 alkyl group may be substituted);
(Eaa21) dibenzofuryloxy group;
(Eaa22) 2H-chromenyloxy group (on the 2H-chromen ring, at least one oxo group may be substituted);
(Eaa23) benzisoxazolyloxy group;
(Eaa24) quinoxalyloxy group;
(Eaa 25) 2,3-dihydro-1H-indenyloxy group (at least one oxo group may be substituted on the 2,3-dihydro-1H-indene ring);
(Eaa26) benzofurananyloxy group;
Or
(Eaa27) phenyl C2-6 alkenyl group (a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group on the phenyl ring At least one of may be substituted)
Indicates );
E11) A group represented by general formula (Eab):

(Wherein, o is as defined above, W ₁ is a C 1-6 alkylene group, and R ¹⁵ is
(Eab1) hydrogen atom;
(Eab2) a C1-6 alkyl group (on the alkyl group, a morpholino group, a benzoyl group, a carbamoyl group optionally having a C1-6 alkyl group as a substituent, or a cyano group may be substituted);
(Eab3) C3-8 cycloalkyl group;
(Eab4) phenyl C1-6 alkyl group (on the phenyl ring, a halogen atom, cyano group, phenyl group, nitro group, C1-6 alkylthio group, C1-6 alkylsulfonyl group, phenyl C1-6 alkoxy group, C2 At least one group selected from the group consisting of 6 alkanoyloxy groups, halogen-substituted or unsubstituted C1-6 alkyl groups, halogen-substituted or unsubstituted C1-6 alkoxy groups and 1,2,3-thiadiazole groups is May be substituted);
(Eab5) C2-6 alkenyl group;
(Eab6) phenyl group (at least one of a group selected from the group consisting of a halogen atom, a cyano group, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group on a phenyl ring Species may be substituted);
(Eab7) C1-6 alkanoyl group;
(Eab8) phenyl C2-6 alkanoyl group (group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group on the phenyl ring At least one of which may be substituted);
(Eab9) Benzoyl group (at least one member selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group, and a halogen-substituted or unsubstituted C1-6 alkoxy group on a benzene ring May be substituted);
(Eab10) C1-20 alkoxycarbonyl group (selected from the group consisting of a halogen atom, an amino group which may have a C1-6 alkyl group as a substituent, and a C1-6 alkoxy substituted C1-6 alkoxy group on the alkoxy group At least one of the substituted groups may be substituted);
(Eab11) phenyl C1-6 alkoxycarbonyl group (in the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group, a halogen substituted or unsubstituted C1-6 alkoxy group, a nitro group, a halogen substituted or Selected from the group consisting of an unsubstituted C1-6 alkylthio group, an amino group which may have a C1-6 alkanoyl group, a phenyl C1-6 alkoxy group, a C1-6 alkoxycarbonyl group and a 1,2,3-thiadiazolyl group At least one of the aforementioned groups may be substituted);
(Eab12) phenyl C3-6 alkenyloxycarbonyl group (on the phenyl ring, selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group At least one of the groups may be substituted);
(Eab13) Phenoxycarbonyl group (on the phenyl ring, at least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group May be substituted);
(Eab14) phenyl C1-6 alkylcarbamoyl group (group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group on the phenyl ring At least one of which may be substituted);
(Eab15) phenylcarbamoyl group (in which at least one group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group on a phenyl ring May be substituted);
(Eab16) benzofuryl-substituted C1-6 alkoxycarbonyl group (on the benzofuran ring, at least one halogen atom may be substituted);
(Eab17) benzothienyl C1-6 alkoxycarbonyl group (in which at least one group selected from the group consisting of a halogen atom and a halogen-substituted or unsubstituted C1-6 alkoxy group is substituted on the benzothiophene ring Also good);
(Eab18) naphthyl substituted C1-6 alkoxycarbonyl group;
(Eab19) pyridyl substituted C.sub.1-6 alkoxycarbonyl group (at least one halogen atom may be substituted on the pyridine ring);
(Eab20) furyl-substituted C1-6 alkoxycarbonyl group (on the furan ring, at least one nitro group may be substituted);
(Eab21) thienyl-substituted C1-6 alkoxycarbonyl group (on the thiophene ring, at least one halogen atom may be substituted);
(Eab22) a thiazolyl-substituted C1-6 alkoxycarbonyl group (a C1-6 alkyl group and a phenyl group on the thiazole ring [a phenyl substituted or unsubstituted C1-6 alkyl group is substituted on the phenyl ring; At least one of the groups selected from the group consisting of
(Eab23) a group consisting of a tetrazolyl substituted C1-6 alkoxycarbonyl group (a C1-6 alkyl group and a phenyl group on the tetrazole ring [at least one halogen atom may be substituted on the phenyl ring]) At least one of the selected groups may be substituted);
(Eab24) 2,3-dihydro-1H-indenyloxycarbonyl group;
(Eab 25) adamantane substituted C1-6 alkoxycarbonyl group;
(Eab26) phenyl C3-6 alkynyloxycarbonyl group;
(Eab27) phenylthio C1-6 alkoxycarbonyl group;
(Eab28) phenyl C1-6 alkoxy substituted C1-6 alkoxycarbonyl group;
(Eab29) C2-6 alkenyloxycarbonyl group;
(Eab30) C2-6 alkynyloxycarbonyl group;
(Eab31) C3-8 cycloalkyl substituted C1-6 alkoxycarbonyl group;
Or
(Eab32) A benzoyl substituted C1-6 alkoxycarbonyl group is shown. );
E12) A group represented by general formula (Eb):

(In the formula, the dotted line indicates that it may be a double bond. R ¹⁶ represents the same group as R ^15. )
E13) A group represented by formula (Ec):

(Wherein R ¹⁷ is
(Ec1) phenyl C1-6 alkyl group (on the phenyl ring, a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group At least one may be substituted);
(Ec2) C1-6 alkoxycarbonyl group;
Or
(Ec3) phenyl C1-6 alkoxycarbonyl group (a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group on the phenyl ring At least one of may be substituted)
Indicates );
E14) a pyridyl group;
E15) A group represented by formula (Ee):

(Wherein, R ⁴⁶ is selected from the group consisting of a halogen atom as a substituent, a halogen-substituted or unsubstituted C1-6 alkyl group, and a halogen-substituted or unsubstituted C1-6 alkoxy group on a phenyl group [phenyl ring At least one of the substituted groups may be substituted); phenyl C.sub.1-6 alkyl group [in the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1 group;少 な く と も 6 alkoxy group may be substituted by at least one group selected from the group consisting of ア ル コ キ シ 6 alkoxy group]; phenyl C1-6 alkoxycarbonyl group [on the phenyl ring, a halogen atom, halogen substituted or unsubstituted C1 1〜6 6 At least one group selected from the group consisting of alkyl groups and halogen substituted or unsubstituted C1-6 alkoxy groups is substituted And each may be a] or an C1~6 alkoxycarbonyl group).;
E16) a phenoxy group (on the phenyl ring, at least one of a group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group is substituted May));
E17) Benzoyl group (in which at least one member selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group is substituted on a phenyl ring May));
E18) 8-azabicyclo [3,2,1] octyl group (8-azabicyclo [3,2,1] octane ring, at least one phenoxy group (phenyl ring, halogen atom, halogen substituted or substituted At least one of a group selected from the group consisting of an unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted);
E19) A group represented by formula (Ef):
-CH = N-NR ⁴⁷ R ⁴⁸ (Ef)
(Wherein R ⁴⁷ and R ⁴⁸ are the same or different and each is a hydrogen atom; a C1-6 alkyl group; a phenyl group [on a phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted Or at least one of a group selected from the group consisting of unsubstituted C1-6 alkoxy groups may be substituted or a pyridyl group [on the pyridine ring, halogen-substituted or unsubstituted C1-6 as a substituent group And at least one alkyl group may be substituted], and R ⁴⁷ and R ⁴⁸ together with their adjacent nitrogen atoms are bonded to each other via or without other heteroatoms. It may form a saturated heterocyclic ring of up to 7-membered ring, on which at least one phenyl group may be substituted as a substituent [on a phenyl ring, a halogen atom, halogen-substituted or Unsubstituted C1~6 alkyl group and at least one halogen substituted or group selected from the group consisting of C1~6 alkoxy group unsubstituted may be substituted] may be substituted).;
E20) phenyl C1-6 alkoxy group (in the phenyl ring, at least one group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group One may be substituted);
E21) Amino-substituted C2-6 alkenyl group (wherein on the amino group, a C1-6 alkyl group and a phenyl group [a phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or not substituted At least one group selected from the group consisting of a group selected from the group consisting of a substituted C1-6 alkoxy group may be substituted);
Or
E22) Oxazolidinyl group (at least one oxo group may be substituted on the oxazolidine ring)
Indicates ]

The group represented by formula (F):
-NR ¹⁹ R ²⁰ (F)
[Wherein, R ¹⁹ and R ²⁰ are the same or different,
F1) hydrogen atom;
F2) C1-6 alkyl;
F3) phenyl C1-6 alkyl group (on the phenyl ring phenoxy group [on the phenyl ring, halogen atoms, halogen substituted or unsubstituted C1-6 alkyl groups and halogen substituted or unsubstituted C1-6 alkoxy groups At least one group selected from the group consisting of: a halogen atom; a halogen-substituted or unsubstituted C.sub.1-6 alkyl group; a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group; On an amino group, a C1-6 alkyl group and a phenyl C1-6 alkyl group [on a phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group At least one group selected from the group consisting of: at least one group selected from the group consisting of Also one kind may be substituted; piperazinyl group [in the piperazine ring at least one phenyl C1-6 alkyl group (on the phenyl ring, a halogen atom, halogen substituted or unsubstituted C1-6 alkyl And at least one of a group selected from the group consisting of halogen substituted or unsubstituted C1-6 alkoxy group may be substituted) and piperidyl group [on the piperidine ring At least one amino group may be substituted on the phenyl group (a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted group on the phenyl group). At least one of a group selected from the group consisting of C1-6 alkoxy groups optionally substituted) and a group consisting of C1-6 alkyl groups . And at least one may be substituted] comprising at least one group selected from the group may be substituted with a group);
F4) a phenoxy C1-6 alkyl group (on the phenyl ring, a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group At least one may be substituted);
F5) amino C1-6 alkyl group (on the amino group, C1-6 alkyl group, C1-6 alkoxycarbonyl group and phenyl group [on the phenyl ring, a halogen atom or halogen substituted or unsubstituted C1-6 alkyl group At least one group selected from the group consisting of groups may be substituted] and at least one group selected from the group consisting of groups may be substituted);
F6) a phenyl group (on the phenyl ring, a halogen atom, on a phenoxy group [the phenyl ring is composed of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group At least one group selected from the group may be substituted] and at least one group selected from the group consisting of a C1-6 alkoxycarbonyl group may be substituted);
F7) C1-6 alkoxycarbonyl group;
F8) phenyl C1-6 alkoxycarbonyl group (group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group on the phenyl ring At least one of which may be substituted);
F9) A group represented by general formula (Fa):

(Wherein, R ²¹ represents a C1-6 alkoxycarbonyl group; a phenyl C1-6 alkoxycarbonyl group (on the phenyl ring, a halogen atom, a cyano group, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or At least one group selected from the group consisting of unsubstituted C1-6 alkoxy groups may be substituted; phenyl C1-6 alkyl group (on the phenyl ring, a halogen atom and halogen substituted or unsubstituted) Or at least one of a group selected from the group consisting of C1-6 alkyl groups may be substituted) or a phenyl group (on the phenyl ring, a halogen atom, a cyano group, a halogen substituted or unsubstituted C1 6 alkyl group and at least one group selected from the group consisting of halogen substituted or unsubstituted C1-6 alkoxy group is substituted Even though it may) shows a).;
F10) 1-substituted-4-piperidyl group represented by formula (Fb):

(Wherein R ²² represents a C1 to 6 alkoxycarbonyl group; a phenyl C1 to 6 alkoxycarbonyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1 to 6 alkyl group and a halogen substituted or unsubstituted At least one of a group selected from the group consisting of a C1-6 alkoxy group may be substituted) or a phenyl group (on the phenyl ring, a halogen atom, a cyano group, a halogen substituted or unsubstituted C1-6, At least one of a group selected from the group consisting of an alkyl group or a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted) or
F11) Piperidyl C1-6 alkyl group (on the piperidine ring, at least one phenoxy group (on the phenyl ring, at least one halogen-substituted or unsubstituted C1-6 alkyl group may be substituted) May substitute)
Indicates ;
F12) Further, R ¹⁹ and R ²⁰ together with the nitrogen atom to which they are adjacent are bonded to each other without or through other hetero atoms or carbon atoms and are shown in the following (F12-1) to (F12-10) It may form a heterocyclic ring. ;
(F12-1) A group represented by general formula (Fc):

[Here, dotted lines indicate that they may be double bonds. R ²³ is
(Fc1) C1-6 alkyl group;
(Fc2) phenyl C1-6 alkyl group (group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group on the phenyl ring At least one of which may be substituted);
(Fc3) phenyl group (a halogen atom on a phenyl ring; halogen substituted or unsubstituted C1-6 alkyl group; halogen substituted or unsubstituted C1-6 alkoxy group; C1-6 alkyl group as a substituent and phenyl C1 To at least one member selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group, and a halogen-substituted or unsubstituted C1-6 alkoxy group on the phenyl ring Amino group which may have a group selected from the group consisting of: phenoxy group [on the phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted group; At least one group selected from the group consisting of C1-6 alkoxy groups may be substituted], phenyl Cア ル コ キ シ 6 alkoxy group [in which at least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group, and a halogen-substituted or unsubstituted C1-6 alkoxy group is substituted on a phenyl ring And at least one amino group may be substituted on the piperidine ring, and a phenyl C.sub.1-6 alkyl group (on the phenyl ring may be substituted on the amino group. At least one group selected from the group consisting of halogen atoms, halogen substituted or unsubstituted C1-6 alkyl groups and halogen substituted or unsubstituted C1-6 alkoxy groups may be substituted) and C1-6 alkyl At least one kind of the group selected from the group consisting of at least one kind of the group selected from the group consisting of Good);
(Fc4) phenyl C1-6 alkoxy group (a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group on the phenyl ring At least one of which may be substituted);
(Fc5) biphenylyl C1-6 alkoxy group;
(Fc6) a phenyl C3-6 alkenyloxy group which may be substituted by at least one halogen atom on the phenyl ring;
(Fc7) phenoxy group (on the phenyl ring, a group selected from the group consisting of a halogen atom, a cyano group, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group At least one may be substituted);
(Fc8) Benzoyl group (at least one group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group on a phenyl ring May be substituted);
(Fc9) C1-6 alkoxycarbonyl group;
(Fc10) phenyl C1-6 alkoxycarbonyl group (on the phenyl ring, at least one halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted);
(Fc11) a phenylC1-6 alkylcarbamoyl group which may be substituted by at least one halogen atom on the phenyl ring;
(Fc12) phenylcarbamoyl group (in which at least one group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group on a phenyl ring May be substituted);
(Fc 13) a phenylthio group (on the phenyl ring, at least one halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted);
(Fc14) phenyl sulfoxide (on the phenyl ring, at least one halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted);
(Fc15) pyridyl C1-6 alkoxy group;
Or
(Fc16) A group represented by general formula (Fca):
-(C = O) o -NR ²⁴ R ²⁵ (Fca)
(In the formula, o is the same as above. R ²⁴ and R ²⁵ are each
(Fca1) hydrogen atom;
(Fca2) C1-6 alkyl group;
(Fca3) phenyl C1-6 alkyl group (group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group on the phenyl ring At least one of which may be substituted);
(Fca4) phenyl group (on the phenyl ring, a group selected from the group consisting of a halogen atom, a cyano group, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group At least one may be substituted);
(Fca5) C1-6 alkanoyl group;
(Fca6) a phenyl C 2-6 alkanoyl group which may be substituted by at least one halogen atom on the phenyl ring;
(Fca7) Benzoyl group (at least one member selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group on a phenyl ring May be substituted);
(Fca8) C1-6 alkoxycarbonyl group;
(Fca9) phenyl C1-6 alkoxycarbonyl group (on the phenyl ring, selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group At least one of the groups may be substituted);
(Fca10) phenylcarbamoyl group (on the phenyl ring, at least one halogen-substituted or unsubstituted C1-6 alkyl group may be substituted);
Or
(Fca11) Piperidyloxycarbonyl group (a phenyl group as a substituent group on the piperidine ring [a halogen-substituted or unsubstituted C1 to C6 alkyl group may be optionally substituted on the phenyl ring]) is at least 1 It may be replaced individually.)
Indicates ;
(Fca12) R ²⁴ and R ²⁵ may form a 5- to 6-membered saturated heterocyclic ring via the nitrogen atom to which they are adjacent. On the heterocycle, a C1-6 alkoxycarbonyl group; a benzoyl group (on a phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group At least one of the groups selected from the group may be substituted; phenoxy group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1 6 at least one group selected from the group consisting of alkoxy groups may be substituted; phenyl C1-6 alkyl group (on the phenyl ring, a halogen atom, halogen substituted or unsubstituted C1-6 alkyl group And at least one of a group selected from the group consisting of halogen-substituted or unsubstituted C.sub.1-6 alkoxy groups A phenyl C1-6 alkoxycarbonyl group (on the phenyl ring, selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group; At least one of the above-mentioned groups may be substituted); phenyl C2-6 alkenyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1 And at least one group selected from the group consisting of 6 alkoxy groups may be substituted) and a phenyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or Even if at least one of the groups selected from the group consisting of unsubstituted C1-6 alkoxy groups is substituted At least one group selected from the group may be substituted consisting have))
Indicates ];
(F12-2) 4-substituted-1-piperazinyl group represented by General Formula (Fd):

(Wherein R ²⁶ is
(Fd1) hydrogen atom;
(Fd2) C1-6 alkyl group;
(Fd3) C3-8 cycloalkyl group;
(Fd4) C3-8 cycloalkyl C1-6 alkyl group;
(Fd5) C1-6 alkoxycarbonyl C1-6 alkyl group;
(Fd6) phenyl C2-6 alkenyl group;
(Fd7) phenyl C1-6 alkyl group (a halogen atom on the phenyl ring; cyano group; halogen substituted or unsubstituted C1-6 alkyl group; C3-8 cycloalkyl group; halogen substituted or unsubstituted C1-6 Alkoxy group; amino group which may have C1-6 alkyl group as a substituent; C1-6 alkoxycarbonyl group; phenoxy group; phenyl C1-6 alkyl group; phenyl C2-6 alkenyl group; pyridyl group; imidazolyl group and piperidyl One to three groups selected from the group consisting of groups may be substituted);
(Fd8) biphenylyl C1-6 alkyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group, a halogen substituted or unsubstituted C1-6 alkoxy group and a C1-6 alkyl as a substituent At least one group selected from the group consisting of amino groups which may have a group may be substituted);
(Fd9) naphthyl C1-6 alkyl group;
(Fd10) phenyl group (a halogen atom on a phenyl ring; cyano group; amino group which may have a C1-6 alkyl group as a substituent; halogen substituted or unsubstituted C1-6 alkyl group; halogen substituted or not Substituted C1-6 alkoxy group; C1-6 alkoxycarbonyl group; carboxyl group; phenoxy group [in the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 At least one of a group selected from the group consisting of an alkoxy group may be substituted; amino C1-6 alkyl group [a phenyl group on an amino group (a halogen atom on a phenyl ring, halogen substitution or It is selected from the group consisting of an unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group And at least one group selected from the group consisting of C1-6 alkyl groups] and phenyl C1-6 alkoxy group [phenyl On the ring, at least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted. And at least one of the groups selected from the group consisting of
(Fd11) biphenylyl group (in the phenyl ring, at least one halogen-substituted or unsubstituted C1-6 alkyl group may be substituted);
(Fd12) amino group, amino group substituted with C1-6 alkoxycarbonyl group, phenyl C1-6 alkylamino group (wherein at least one halogen-substituted or unsubstituted C1-6 alkyl group is substituted on the phenyl ring Or a phenylamino group (in the phenyl ring, at least one of a group selected from the group consisting of a halogen atom and a halogen-substituted or unsubstituted C1-6 alkyl group may be substituted);
(Fd13) benzoyl C1-6 alkyl group (wherein at least one halogen atom may be substituted on the phenyl ring);
(Fd14) phenylcarbamoyl C1-6 alkyl group (wherein at least one halogen-substituted or unsubstituted C1-6 alkyl group may be substituted on the phenyl ring);
(Fd15) thiazolyl C1-6 alkyl group (on the thiazole ring, at least one group selected from the group consisting of halogen-substituted or unsubstituted phenyl group and C1-6 alkyl group may be substituted) ;
(Fd16) an oxazolyl C1-6 alkyl group (on the oxazolyl ring, at least one of a group selected from the group consisting of a halogen-substituted or unsubstituted phenyl group and a C1-6 alkyl group is substituted Good);
(Fd17) indolyl C1-6 alkyl group;
(Fd18) furyl C1-6 alkyl group (wherein at least one halogen-substituted or unsubstituted phenyl group may be substituted on the furan ring);
(Fd19) imidazolyl C1-6 alkyl group (phenyl group may be substituted on imidazole ring);
(Fd20) quinolyl C1-6 alkyl group;
(Fd21) a tetrazolyl group (a phenyl group may be substituted on the tetrazole ring);
(Fd22) a pyrimidyl group which may be substituted by a phenyl group;
(Fd23) pyridyl group;
(Fd24) benzoxazolyl group;
(Fd25) benzothiazolyl group;
(Fd26) benzoxazolyl C1-6 alkyl group (on the benzoxazole ring, at least one oxo group may be substituted);
(Fd27) a phenoxy C2-6 alkanoyl group which may be substituted by a halogen atom on the phenyl ring;
(Fd28) a phenylthio C2-6 alkanoyl group which may be substituted by a halogen atom on the phenyl ring;
(Fd29) phenyl C2-6 alkanoyl group (a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group on the phenyl ring At least one of which may be substituted);
(Fd30) benzoyl group (having a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group, a halogen-substituted or unsubstituted C1-6 alkoxy group and a C1-6 alkyl group as a substituent group on the phenyl ring At least one group selected from the group consisting of a certain amino group may be substituted);
(Fd31) biphenylyl carbonyl group;
(Fd32) pyridylcarbonyl group;
(Fd33) a phenyl C2-6 alkenyl carbonyl group which may be substituted by a halogen atom on the phenyl ring;
(Fd34) a phenylC1-6 alkylsulfonyl group which may be substituted by a halogen atom on the phenyl ring;
(Fd35) benzenesulfonyl group (on the benzene ring, at least one of a group selected from the group consisting of a halogen atom and a C1-6 alkyl group may be substituted);
(Fd36) a group represented by formula (Fda):
-COOR ²⁷ (Fda)
(In the formula, R ²⁷ is
(Fda1) halogen-substituted or unsubstituted C1-8 alkyl group;
(Fda2) C3 to C8 cycloalkyl group;
(Fda3) C3-C8 cycloalkyl-C1-6 alkyl group;
(Fda4) C1-6 alkoxy-C1-6 alkyl group;
(Fda5) amino-C1-6 alkyl group which may have C1-6 alkyl group;
(Fda6) a group represented by the general formula (Fdb)

(Wherein R ²⁸ , R ²⁹ and R ³⁰ each represent a hydrogen atom; a C 1-6 alkyl group; a phenyl group (on a phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C 1-6 alkyl group and a halogen-substituted or At least one group selected from the group consisting of unsubstituted C1-6 alkoxy groups may be substituted).
(Fda7) phenyl C1-6 alkyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group, a halogen substituted or unsubstituted C1-6 alkoxy group, a halogen substituted or unsubstituted C1 To 6 alkylthio group, phenyl C1-6 alkoxy group, hydroxy group, C1-6 alkylsulfinyl group, C1-6 alkylsulfonyl group, C1-6 alkylsulfonyloxy group, cyano group, C1-6 alkanoyl group, benzoyl group, alkyl Phenyl C1-6 alkyl group which may have C1-6 alkoxy group in part, amino group, nitro group, carbamoyl group, C1-6 alkanoylamino group, C1-6 alkoxycarbonyl group, C1-6 alkylamino carbonyl group, C1-6 alkoxycarbonylamino group, tri C1- A group selected from the group consisting of 6 alkylsiloxy group, pyrrolyl group, tetrahydropyranyloxy group and imidazolyl group may be substituted by 1 to 5);
(Fda8) biphenylyl C1-6 alkyl group;
(Fda9) a benzhydryl group (on the benzene ring, at least one of a group selected from the group consisting of a halogen atom, a trifluoromethyl group and a trifluoromethoxy group may be substituted);
(Fda10) a phenoxy C1-6 alkyl group (a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group on the phenyl ring At least one of which may be substituted);
(Fda11) phenyl C2-6 alkynyl group (wherein at least one halogen-substituted or unsubstituted C1-6 alkyl group may be substituted on the phenyl ring);
(Fda12) pyridyl C1-6 alkyl group;
(Fda13) a group represented by the general formula (Fdc)

(Wherein R ³¹ represents a group consisting of a halogen atom, a cyano group, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group on a phenyl group [phenyl ring At least one selected group may be substituted; phenyl C1-6 alkyl group [wherein on a phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted Or at least one of a group selected from the group consisting of C1-6 alkoxy groups may be substituted or a benzoyl group [on the phenyl ring, a halogen atom or a halogen substituted or unsubstituted C1-6 alkyl group And at least one of a group selected from the group consisting of halogen-substituted or unsubstituted C1-6 alkoxy groups may be substituted Be).;
(Fda14) piperidino C1-6 alkyl group (a phenoxy group which may have at least one halogen-substituted or unsubstituted alkyl group as a substituent on the phenyl ring on the piperidine ring may be substituted);
(Fda15) amino C1-6 alkyl group (group comprising a C1-6 alkyl group on the amino group and a phenyl group which may have a halogen-substituted or unsubstituted C1-6 alkoxy group as a substituent on the phenyl ring At least one of the selected groups may be substituted);
(Fda16) 1,2,3,6-tetrahydropyridyl C1-6 alkyl group (1,2,3,6-tetrahydropyridine ring, at least one phenyl group [phenyl ring or halogen substitution or At least one unsubstituted C1-6 alkoxy group may be substituted];
(Fda17) naphthyl C1-6 alkyl group;
(Fda18) fluorenyl C1-6 alkyl group;
(Fda19) pyridyl C1-6 alkyl group;
(Fda20) furyl C1-6 alkyl group (a halogen-substituted or unsubstituted phenyl group may be substituted on the furan ring);
(Fda21) thienyl C1-6 alkyl group;
(Fda22) oxazolyl C1-6 alkyl group (a halogen atom or a halogen-substituted or unsubstituted phenyl group may be substituted on the oxazole ring);
(Fda23) oxadiazolyl C1-6 alkyl group (a halogen-substituted or unsubstituted phenyl group may be substituted on the oxadiazole ring);
(Fda24) pyrazolyl C1-6 alkyl group (a halogen-substituted or unsubstituted phenyl group may be substituted on the pyrazole ring);
(Fda 25) benzothienyl C1-6 alkyl group (in which at least one group selected from the group consisting of a halogen atom and a halogen substituted or unsubstituted C1-6 alkoxy group is substituted on the benzothiophene ring Good);
(Fda26) a thienyl C1-6 alkyl group which may be substituted by a halogen atom on the thiophene ring;
(Fda27) benzothiazolyl C1-6 alkyl group;
(Fda28) a benzofuryl C1-6 alkyl group which may be substituted by a halogen atom on the benzofuran ring;
(Fda29) indolinyl C1-6 alkyl group (on the indoline ring, at least one of a group selected from the group consisting of a C1-6 alkyl group and an oxo group may be substituted);
(Fda30) benzoxazolyl C1-6 alkyl group (on the benzoxazole ring, at least one of a group selected from the group consisting of a halogen atom, a C1-6 alkyl group and an oxo group may be substituted );
(Fda31) chromenyl C1-6 alkyl group;
(Fda32) 1,2,3,4-tetrahydroquinolyl C1-6 alkyl group (on the quinoline ring, at least one of a group selected from the group consisting of a C1-6 alkyl group and an oxo group is substituted May)
(Fda33) thiazolyl C1-6 alkyl group (wherein at least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted phenyl group and a C1-6 alkyl group is substituted on the thiazole ring Also good);
Or
(Fda34) tetrazolyl C1-6 alkyl group (on the tetrazole ring, at least one group selected from the group consisting of halogen-substituted or unsubstituted phenyl group and C1-6 alkyl group may be substituted)
Indicates );
(Fd37) a group represented by the general formula (Fe):
-Z-NR ³² R ³³ (Fe)
(Wherein, Z represents -C = O or -C = S. R ³² and R ³³ are the same or different, and
(Fe1) hydrogen atom;
(Fe2) C1-6 alkyl group;
(Fe3) C3-8 cycloalkyl group;
(Fe4) phenyl C1-6 alkyl group (group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group on the phenyl ring At least one of which may be substituted);
(Fe5) phenyl C2-6 alkenyl group (group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group on the phenyl ring At least one of which may be substituted);
Or
(Fe6) phenyl group (on the phenyl ring, at least one group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group, and a halogen substituted or unsubstituted C1-6 alkoxy group May substitute)
Indicates ;
(Fe7) Alternatively, R ³² and R ³³ may be bonded to each other via the other carbon atom together with the nitrogen atom to which they are adjacent to form a piperidine ring or a 1,2,3,6-tetrahydropyridine ring . A phenyl group may be substituted on the piperidine ring and the 1,2,3,6-tetrahydropyridine ring, and the phenyl group is a group consisting of a halogen atom and a halogen substituted or unsubstituted C1-6 alkyl group. At least one of the selected groups may be substituted. );
(Fd38) group represented by formula (Ff):

(Wherein, R ³⁴ represents a hydrogen atom or a C 1-6 lower alkyl group. R ³⁵ represents
(Ff1) C3-8 cycloalkyl group;
(Ff2) C3-8 cycloalkenyl group;
(Ff3) group represented by the general formula (Ffa):

(Wherein R ³⁶ , R ³⁷ and R ³⁸ each represent a hydrogen atom; a C 1-6 alkyl group; a phenyl group [wherein a halogen atom, a halogen substituted or unsubstituted C 1-6 alkyl group, a halogen substituted Or unsubstituted C1-6 alkoxy, C1-4 alkylenedioxy, C1-6 alkylsulfonyl, halogen substituted or unsubstituted C1-6 alkylthio, nitro and C1-6 alkanoyl as a substituent Or at least one group selected from the group consisting of amino groups may be substituted with 1 to 5 groups; benzofuryl group [on the benzofuran ring, a halogen atom, a halogen substituted or unsubstituted C1- At least one of a group selected from the group consisting of a 6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group is substituted A biphenylyl group or a furyl group [a phenyl group which may have a halogen atom as a substituent may be substituted on the furan ring] or a thiazolyl group [a halogen atom on a thiazol ring At least one phenyl group which may be substituted may be substituted.
(Ff4) phenyl group (a halogen atom on the phenyl ring; halogen substituted or unsubstituted C1-6 alkyl group; C3-8 cycloalkyl group; hydroxyl group; halogen substituted or unsubstituted C1-8 alkoxy group C3-8 cycloalkoxy group; C1-4 alkylenedioxy group; cyano group; nitro group; phenyl C2-6 alkenyl group; C2-6 alkanoyloxy group; amino sometimes having C1-6 alkanoyl group as a substituent Group: C1-6 alkylsulfonylamino group; phenyl C1-6 alkoxy group; phenoxy group; amino group substituted with at least one C1-6 alkyl group; amino group substituted with at least one phenyl group; amino C1-6 alkoxy Group [in the amino group, at least one C1-6 alkyl group may be substituted] C1-6 alkoxycarbonyl group; C1-6 alkoxycarbonyl C1-6 alkoxy group; C1-6 alkylthio group; pyrrolyl group; imidazolyl group; piperidyl group; morpholino group; pyrrolidinyl group; thienyl group; benzofuryl group; piperazinyl group [piperazine ring And at least one group selected from the group consisting of a benzoyl group which may have at least one of a C1-6 alkyl group, a phenyl C1-6 alkyl group and a C1-6 alkyl group as a substituent A quinolyl group [in which at least one group selected from the group consisting of a C1-6 alkoxy group and an oxo group may be substituted on a quinoline ring]; a carbostyryl group on a piperidine ring Selected from the group consisting of optionally substituted piperidyl carbonyl group and triazolyl group At least one may be substituted groups);
(Ff5) a naphthyl group (a group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkoxy group and a C1-6 alkyl group as a substituent on the naphthalene ring At least one of which may be substituted);
(Ff6) biphenylyl group (on the biphenylyl ring, at least one group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-9 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group May be substituted);
(Ff7) fluorenyl group; pyrenyl group;
(Ff8) benzofuryl group (in the benzofuran ring, at least one group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group is May be substituted);
(Ff9) a benzothienyl group (on the benzothiophene ring, at least one of a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group Species may be substituted);
(Ff10) a pyridyl group (a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group on a pyridine ring, a phenyl group [a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group on a phenyl ring, And at least one group selected from the group consisting of halogen substituted or unsubstituted C1-6 alkoxy group may be substituted], at least one group selected from the group consisting of furyl group and thienyl group May be substituted);
(Ff11) Furyl group (C1-6 alkyl group on the furan ring, nitro group and phenyl group [on the phenyl ring, halogen atom, halogen substituted or unsubstituted C1-6 alkyl group, halogen substituted or not At least one group selected from the group consisting of a substituted C1-6 alkoxy group and a nitro group may be substituted with one to three groups selected from the group consisting of );
(Ff12) a benzothiazole group (on the benzothiazole ring, at least one phenyl group which may have a C1 to C6 alkoxy group on the phenyl ring as a substituent may be substituted);
(Ff13) Thienyl group (a halogen atom, a nitro group, a C1-6 alkyl group on the thiophene ring, a pyrazolyl which may be substituted at least one halogen-substituted or unsubstituted C1-6 alkyl group on the pyrazole ring And at least one group selected from the group consisting of a group and a thienyl group which may be substituted by a halogen atom on the thiophene ring may be substituted);
(Ff14) an indolyl group (selected from the group consisting of a phenylsulfonyl group which may have a C1-6 alkyl group as a substituent, an phenyl C1-6 alkyl group, a C1-6 alkoxycarbonyl group and a phenyl group on the indole ring At least one of the substituted groups may be substituted);
(Ff15) a pyrrolyl group (on the pyrrole ring, a group selected from the group consisting of a phenyl group which may be substituted by at least one halogen-substituted or unsubstituted C1-6 alkyl group and a C1-6 alkyl group; At least one may be substituted);
(Ff 16) coumaryl group;
(Ff17) benzoimidazolyl group (on the benzimidazole ring, at least one thienyl group may be substituted);
(Ff 18) an oxazolyl group (on the oxazole ring, at least one phenyl group which may have a halogen atom may be substituted);
(Ff19) thiazolyl group (at least one phenyl group may be substituted on a thiazole ring. On the phenyl ring, a group selected from the group consisting of a halogen atom, a nitro group and a phenyl group At least one kind may be substituted));
(Ff21) quinolyl group;
(Ff22) 3,4-dihydrocarbostyryl group (a group selected from the group consisting of a C1-6 alkoxy group, a C1-6 alkyl group and a phenyl C1-6 alkoxy group on the 3,4-dihydrocarbostyryl ring Or a group selected from the group consisting of a C1-6 alkoxy group, a C1-6 alkyl group and a phenyl C1-6 alkoxy group on the carbostyryl ring At least one of which may be substituted);
(Ff23) imidazo [2,1-b] thiazolyl group;
(Ff24) imidazo [2,1-a] pyridyl group;
(Ff 25) a chromanyl group (on the chroman ring, at least one C1-6 alkyl group may be substituted);
Or
(Ff26) A 2,3-dihydrobenzofuryl group is shown. );
Or
(Fd39) a group represented by formula (Ffb):

(Wherein R ⁴⁵ represents a C1 to 6 alkoxycarbonyl group; a phenyl group [wherein a halogen atom, a halogen substituted or unsubstituted C1 to 6 alkyl group and a halogen substituted or unsubstituted C1 to 6 alkoxy group on a phenyl ring Amino-substituted C.sub.1-6 alkyl group [on the amino group, a phenyl group (on the phenyl ring, a halogen atom, or a halogen-substituted or non-halogenated group; At least one group selected from the group consisting of a substituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group may be substituted) and a C1-6 alkyl group selected At least one of the groups may be substituted]; benzoyl group [on the phenyl ring, a halogen atom, halogen substituted or unsubstituted C1-6 aryl And at least one group selected from the group consisting of halogen and a substituted or unsubstituted C.sub.1-6 alkoxy group may be substituted]; phenyl C.sub.1-6 alkyl group [a halogen atom on a phenyl ring And at least one selected from the group consisting of a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted]; phenyl C1-6 alkoxycarbonyl And at least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group is substituted on the phenyl ring. Or a phenyl C 2-6 alkenyl group [on the phenyl ring, a halogen atom, halogen substituted or unsubstituted C It shows a 6 alkyl group and at least one group selected from the group consisting of C1~6 alkoxy group a halogen substituted or unsubstituted may be substituted.)
Indicates )
(F12-3) morpholino group;
(F12-4) imidazolyl group;
(F12-5) 1,4-dioxaazaspiro [4,5] decyl group (1,4-dioxaazaspiro [4,5] decane ring has at least one oxo group substituted thereon May)
(F12-6) Homopiperazinyl group (at least one group selected from the group consisting of a C1-6 alkoxycarbonyl group, a phenyl C1-6 alkoxycarbonyl group, and a phenyl substituted or unsubstituted phenyl group on the homopiperazine ring May be substituted);
(F12-7) Piperazinyl group (in the piperazine ring, an oxo group, a C1-6 alkyl group, a phenyl C1-6 alkyl group [on a phenyl ring, at least one of a halogen-substituted or unsubstituted C1-6 alkyl group And at least one group selected from the group consisting of may be substituted);
(F12-8) piperidyl group (on the piperidine ring, at least one oxo group may be substituted);
(F12-9) pyrrolidinyl group (on the pyrrolidine ring, at least one phenoxy C1-6 alkyl group which may have a halogen-substituted or unsubstituted C1-6 alkoxy group as a substituent may be substituted) ;
Or
(F12-10) is an isoindolinyl group; ;
F13) Further, R ¹⁹ and R ²⁰ are bonded to each other together with the adjacent nitrogen atom, with or without a heteroatom, to form a cyclic imide or amide represented by (F13-1) to (F13-11) below You may form.

(F13-1) succinimide group;
(F13-2) oxazolidinyl group (on the oxazolidine ring, at least one oxo group may be substituted);
(F13-3) Benzo-1,3-oxazolidinyl group (On the benzo-1,3-oxazolidine ring, at least one of a group selected from the group consisting of an oxo group, a halogen atom and a phenyl group is substituted May)
(F13-4) Imidazolidinyl group (On an imidazolidine ring, an oxo group, a phenyl C1-6 alkyl group [a phenyl ring, a group selected from the group consisting of a halogen atom and a C1-6 alkoxy group is selected At least one of a group selected from the group consisting of a phenyl group and a phenyl group may be substituted);
(F13-5) benzoimidazolidinyl group (having an oxo group, a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group, and a C1-6 alkyl group as a substituent on the benzoimidazolidine ring (F13-5) Amino group, C1-6 alkoxycarbonyl group and piperidyl group [C1-6 alkyl group on piperidine ring, phenyl group which may have 1 to 3 halogen atoms substituted on phenyl ring, C1-6 alkoxycarbonyl group At least one group may be substituted with a group selected from the group consisting of a group and at least one group selected from the group consisting of phenyl C1-6 alkoxycarbonyl group);
(F13-6) Phthalimide group;
(F13-7) indolinyl group (in the indoline ring, at least one of a group selected from the group consisting of a C1-6 alkyl group, a halogen atom and an oxo group may be substituted);
(F13-8) 2,3-dihydrobenzothiazolyl group (wherein at least one oxo group may be substituted on the 2,3-dihydrobenzothiazole ring);
(F13-9) 1H-2,4-benzoxazinyl group (at least one oxo group may be substituted on the 1H-2,4-benzoxazine ring);
(F13-10) A group represented by formula (Fga):

(Wherein, R ³⁹ represents a hydrogen atom; a phenyl C 1 to C 6 alkyl group which may have a halogen atom as a substituent on the phenyl ring; a phenoxy C 1 to 6 which may have a halogen atom as a substituent on the phenyl ring An alkyl group; a phenyl C2-6 alkenyl group which may have a halogen atom as a substituent on the phenyl ring; a halogen atom as a substituent on the phenyl ring, a halogen substituted or unsubstituted C1-6 alkyl group, a halogen substituted or not At least one of a group selected from the group consisting of a substituted C1-6 alkoxy group and a phenyl group is an optionally substituted phenyl group; a pyridyl group or a pyrazinyl group is shown)
(F13-11) 1,3-thiazolidinyl group (On the 1,3-thiazolidine ring, an oxo group as a substituent and a halogen-substituted or unsubstituted C1-6 alkyl group on the phenyl ring may be contained. At least one of a group selected from the group consisting of a phenyl C1-6 alkylidene group may be substituted)]

The group represented by formula (G):

(Wherein, R ⁴⁰ represents a C1-6 alkyl group or a halogen-substituted or unsubstituted phenyl group)

(A) phenyl group (at least one piperidyl group on the phenyl ring [at least one phenoxy group on the piperidine ring (a halogen atom on the phenyl ring, halogen-substituted or unsubstituted C1 to C6; At least one of a group selected from the group consisting of an alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group may be substituted) may be substituted) ;

(B) benzothiazolyloxy group (on the benzothiazole ring, (b-1) phenyl group [on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or not substituted. At least one of a group selected from the group consisting of substituted C1-6 alkoxy groups may be substituted, (b-2) piperazinyl group [in the piperazine ring, a phenyl C1-6 alkyl group (phenyl At least one selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted on the ring A phenyl C2-6 alkenyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group or not And at least one of a group selected from the group consisting of: a phenyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted group; Or at least one group selected from the group consisting of C1-6 alkoxy groups of the above group may be substituted), (b-3 A piperidyl group [a piperidine ring, an amino group (an amino group, a phenyl group [a phenyl group, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1 group. -At least one group selected from the group consisting of 6 alkoxy groups may be substituted] and at least one group selected from the group consisting of C1-6 alkyl groups may be substituted) , (In the phenyl ring, at least one of a group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group is substituted. And phenyl C1-6 alkyl group (on the phenyl ring, selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group At least one kind of the aforementioned groups may be substituted), and at least one kind of the group selected from the group consisting of (a) may be substituted], (b-4) pyrrolyl group [on the pyrrole ring, C1-6 alkyl group and phenyl C1-6 alkyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen At least one group selected from the group consisting of a group selected from the group consisting of a substituted or unsubstituted C1-6 alkoxy group may be substituted) And (b-5) phenylthio group [in the phenyl ring, a group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group] At least one group selected from the group consisting of at least one group may be substituted);

(C) quinolyloxy group (in the quinoline ring, (c-1) a halogen atom; (c-2) phenoxy group [in the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen At least one of a group selected from the group consisting of a substituted or unsubstituted C1-6 alkoxy group may be substituted], (c-3) piperazinyl group [a phenyl C1-6 alkyl group on a piperazine ring Group (on the phenyl ring, at least one of a group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group is substituted) (Optional), a phenyl group (on the phenyl ring, a phenoxy group [on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted Is optionally substituted by at least one group selected from the group consisting of unsubstituted C1-6 alkoxy groups], a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted group And at least one group selected from the group consisting of C.sub.1-6 alkoxy groups, and a phenyl C.sub.2-6 alkenyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1) At least one group selected from the group consisting of: at least one group selected from the group consisting of a -6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group; And (c-4) piperidyl group [an amino group (a phenyl group on an amino group, a halogen atom on a phenyl ring, At least one of a group selected from the group consisting of a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group] and a C1-6 alkyl group At least one group selected from the group consisting of: phenoxy group (on the phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted group; At least one of a group selected from the group consisting of a C1-6 alkoxy group may be substituted); a phenyl C1-6 alkyl group (on a phenyl ring, a C1 to 4 alkylenedioxy group, a halogen atom, At least one group selected from the group consisting of a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group 1 type may be substituted; phenyl C1-6 alkoxy group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group At least one group selected from the group consisting of: a phenyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted group; And at least one group selected from the group consisting of C1-6 alkoxy groups may be substituted); naphthyl C1-6 alkyl group and phenyl C1-6 alkylidene group (a halogen atom on the phenyl ring, From the group consisting of halogen-substituted or unsubstituted C1-6 alkyl groups and halogen-substituted or unsubstituted C1-6 alkoxy groups At least one kind of group selected from the group consisting of at least one kind of branched group may be substituted) and at least one kind of group selected from the group consisting of May be);

(D) a pyridyloxy group (a pyridine ring, a (d-1) piperidyl group [a piperidine ring, a phenoxy group (a phenyl atom, a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group, And at least one of a group selected from the group consisting of halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted), phenyl C1-6 alkoxy substituted C1-6 alkyl group (on the phenyl ring) , At least one of a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group may be substituted), phenoxy C1 To a 6 alkyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.6 And at least one group selected from the group consisting of -6 alkoxy groups may be substituted) and a phenyl C1-6 alkyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6, At least one group selected from the group consisting of an alkyl group and at least one group selected from the group consisting of a halogen substituted or unsubstituted C1-6 alkoxy group is substituted And (d-2) piperazinyl group [C1-6 alkoxycarbonyl group on piperazine ring, furyl C1-6 alkyl group (on furan ring, at least one phenyl group [phenyl ring on At least one of a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group (One of which may be substituted) may be substituted), pyridyl C1-6 alkyl group (on the pyridine ring, furyl group and phenyl group [on the phenyl ring, a halogen atom, halogen substitution or At least one of a group selected from the group consisting of an unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group] may be substituted by at least one group selected from the group consisting of (One of which may be substituted), benzothienyl C1-6 alkyl group (on the benzothiophene ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 At least one of a group selected from the group consisting of an alkoxy group may be substituted, a phenyl C 2-6 alkenyl group (on the phenyl ring, a halogen atom, a halogen At least one member selected from the group consisting of a substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group, a benzofuryl C1-6 alkyl group (which may be substituted) At least one member selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group is substituted on the benzofuran ring A benzofuryl C2-6 alkenyl group (on the benzofuran ring, a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group At least one of which may be substituted), a thiazolyl C.sub.1-6 alkyl group (on the thiazole ring, at least one phenyl). The phenyl ring has at least one member selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group. (Optionally substituted), phenoxy C1-6 alkyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 At least one group selected from the group consisting of alkoxy groups may be substituted, indolyl C1-6 alkyl group (on the indole ring, a halogen atom, halogen substituted or unsubstituted C1-6 alkyl group And at least one group selected from the group consisting of halogen-substituted or unsubstituted C1-6 alkoxy groups may be substituted) and phenyl C1-6 aryl A group selected from the group consisting of a benzofuryl group, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group on a phenyl ring At least one kind of groups selected from the group consisting of may be substituted) and at least one kind of groups selected from the group consisting of

(E) 1,2,3,4-tetrahydroquinolyloxy group (in the 1,2,3,4-tetrahydroquinoline ring, an oxo group, a phenyl group [on a phenyl ring, a halogen atom, halogen substitution or At least one of a group selected from the group consisting of an unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted] and a phenyl C1-6 alkyl group [phenyl ring At least one selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group, and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted thereon. And at least one of the groups selected from the group consisting of

(F) 1,2,3,4-tetrahydronaphthyloxy group (at least one oxo group may be substituted on the 1,2,3,4-tetrahydronaphthalene ring);

(G) 2H-chromenyloxyl group (on the 2H-chromen ring, at least one oxo group may be substituted);

(H) Naphthyloxy group (on the naphthalene ring at least one piperidyl group [on the piperidine ring at least one phenoxy group (on the phenyl ring a halogen atom, halogen substituted or unsubstituted C1 6) at least one of a group selected from the group consisting of an alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted) );

(I) 1,2,3,4-tetrahydroisoquinolyloxy group (in the 1,2,3,4-tetrahydroisoquinoline ring, a C1-6 alkoxycarbonyl group, a phenyl C1-6 alkyl group [on a phenyl ring And at least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted Phenyl group [in which at least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group is substituted on a phenyl ring At least one of the groups selected from the group consisting of

(J) group-NR ^{22 '} R ^23'
(R ^{22 ′} represents a hydrogen atom or a C1-6 alkyl group. R ^{23 ′} represents a (j-1) phenyl group [wherein at least one piperidyl group on a phenyl ring (at least one on a piperidine ring 1 phenoxy group [in the phenyl ring, at least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group Is optionally substituted] is substituted), (j-2) phenyl C1-6 alkyl group [on a phenyl ring, a piperidyl group (on a piperidine ring Phenoxy group [on the phenyl ring, at least one group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group, and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group. But Conversion and may be] is assumed to be substituted) and groups ^{-NR 24 'R 25' (R} 24 ' are, .R ²⁵ represents a hydrogen atom or a C1~6 alkyl ^group' is phenyl C2~ 6 alkenyl group [in which at least one group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group is substituted on a phenyl ring In which at least one member selected from the group consisting of is optionally substituted], (j-3) piperidyl C.sub.1-6 alkyl group [on the piperidine ring, At least one phenyl group (on the phenyl ring at least one of the groups selected from the group consisting of halogen atoms, halogen substituted or unsubstituted C.sub.1-6 alkyl groups and halogen substituted or unsubstituted C.sub.1-6 alkoxy groups Species replaced (Optionally substituted), (j-4) thiazolyl group [wherein a phenyl group (on the phenyl ring, a halogen atom, halogen substituted or unsubstituted C1 to C6 is substituted. At least one of piperazinyl C1-6 alkyl groups (on the piperazine ring, at least one of which may be substituted), selected from the group consisting of an alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group; [Phenyl ring and at least one group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group] Optionally substituted) and piperidyl C1-6 alkyl groups (on the piperidine ring, at least one phenoxy group [on the phenyl ring: At least one of a group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group may be substituted Or at least one of the groups selected from the group consisting of) or (j-5) phenyl C.sub.2-6 alkenyl group [on the phenyl ring, a halogen atom, halogen substituted or not, And at least one group selected from the group consisting of a substituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted. );

(K) benzoxazolyloxy group (on a benzoxazole ring, a piperazinyl group [on a piperazine ring, a phenyl C.sub.1-6 alkyl group (on a phenyl ring, a halogen atom, halogen substituted or unsubstituted C.sub.1 6 alkyl group and at least one group selected from the group consisting of halogen substituted or unsubstituted C1-6 alkoxy group may be substituted) and phenyl C2-6 alkenyl group (on the phenyl ring, halogen At least one group selected from the group consisting of an atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted At least one of the selected groups may be substituted], piperidyl group [on the piperidine ring, a phenyl C.sub.1-6 alkyl group ( At least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group on the ring And an amino group (on the amino group, a C1-6 alkyl group and a phenyl group [on a phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1 At least one group selected from the group consisting of 6 alkoxy groups may be substituted], and at least one group may be substituted from the group selected from the group consisting of And at least one group may be substituted] and a phenyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1 At least one group selected from the group consisting of 6 alkoxy group at least one group selected from the group consisting of and may have) substitution assumed to substituted);

(L) benzimidazolyloxy group (on a benzimidazole ring, a C1-6 alkyl group, a phenyl group [a phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted At least one of a group selected from the group consisting of a C1-6 alkoxy group may be substituted, a piperidyl group [at least one phenoxy group on a piperidine ring (a halogen atom on a phenyl ring, At least one of a group selected from the group consisting of a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted A piperazinyl group [in the piperazine ring, at least one phenyl C.sub.1-6 alkyl group (on the phenyl ring, a halogen atom, halo; At least one group selected from the group consisting of substituted or unsubstituted C.sub.1-6 alkyl group and halogen substituted or unsubstituted C.sub.1-6 alkoxy group may be substituted And phenyl C.sub.1-6 alkyl groups [in the phenyl ring, a group selected from the group consisting of halogen atoms, halogen substituted or unsubstituted C.sub.1-6 alkyl groups and halogen substituted or unsubstituted C.sub.1-6 alkoxy groups. At least one group selected from the group consisting of at least one group may be substituted);

(M) 1,2,3,4-tetrahydroisoquinolyl group (on the 1,2,3,4-tetrahydroisoquinoline ring, (m-1) amino group [on amino group, C1-6 alkyl Group, a phenyl group (on the phenyl ring, at least one group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group is And a group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group (which may be substituted) and a phenyl C1-6 alkyl group (on the phenyl ring And at least one group selected from the group consisting of at least one group selected from the group consisting of) may be substituted] and (m-2) phenoxy group [on phenyl ring Is the halo Group selected from the group consisting of a gen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group, and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group; and the group consisting of At least one selected group may be substituted);

(N) piperidyl group (in the piperidine ring, (n-1) phenyl group [in the phenyl ring, at least one group -NR ^{26 '} R ^27' (R ^{26 '} is a hydrogen atom or C 1 to 6 R ^{27 ′} represents a phenyl group [wherein a phenyl group is selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group] At least one kind of the above-mentioned groups may be substituted])) is substituted.], (N-2) group -W ₁ NR ^{28 '} R ^29' [W ₁ is C 1- 6 represents an alkylene group, R ^{28 ′} represents a hydrogen atom or a C1-6 alkyl group, R ^{29 ′} represents a phenyl group (on a phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group And halogen selected from the group consisting of halogen substituted or unsubstituted C1-6 alkoxy group At least one of the groups may be substituted)], a C1-6 alkoxy group substituted by two (n-3) phenyl groups [on the phenyl ring, a halogen atom, a halogen substituted or an unsubstituted group And at least one group selected from the group consisting of a C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group] and (n-4) phenyl C1-6 alkyl groups [At least one phenyl group on the phenyl ring (on the phenyl ring, a group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group. At least one of the groups selected from the group consisting of] may be substituted), and at least one of the selected groups may be substituted);

(O) Piperazinyl group (a C.sub.1-6 alkyl group substituted by two phenyl groups on the piperazine ring [a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or not substituted on the phenyl ring At least one member selected from the group consisting of substituted C1-6 alkoxy groups may be substituted], phenyl C1-6 alkyl group [in the phenyl ring, at least one phenoxy group (phenyl ring Above, at least one of a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group is substituted Embedded image], a thiazolyl group [at least one phenyl group may be substituted on the thiazole ring], Noxy C1-6 alkyl group [on the phenyl ring (on the phenyl ring there is a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group At least one group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group [C2-6 alkenyl group] [wherein on the phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted group are substituted; At least one group selected from the group consisting of C1-6 alkoxy groups is substituted] and imidazo Group [on the imidazole ring, at least one phenyl group (on the phenyl ring, it comprises a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group. At least one of the groups selected from the group may be substituted), and at least one of the groups selected from the group consisting of the groups may be substituted);

(P) a thiazolyl C1-6 alkoxy group (on the thiazole ring, a (p-1) phenoxy C1-6 alkyl group [on a phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen At least one of a group selected from the group consisting of a substituted or unsubstituted C1-6 alkoxy group may be substituted], (p-2) anilino C1-6 alkyl group [on the phenyl ring, a halogen At least one group selected from the group consisting of an atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group], (p-3 ) Phenyl C1-6 alkyl group [on the phenyl ring, selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group (P-4) Piperazinyl C1-6 alkyl group [in the piperazine ring, at least one phenyl group (a halogen atom on the phenyl ring, a halogen atom, a halogen At least one of a group selected from the group consisting of a substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted) And (p-5) piperidyl C.sub.1-6 alkyl group [in the piperidine ring, at least one phenoxy group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or At least one of a group selected from the group consisting of an optionally substituted group selected from the group consisting of an unsubstituted C.sub.1-6 alkoxy group)) There may be substituted);

(q) 8-azabicyclo [3.2.1] octyl group (8-azabicyclo [3.2.1] octane ring, at least one phenoxy group [phenyl ring, halogen atom substituted Or at least one of a group selected from the group consisting of an unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted);

(r) group

[Where X and m are as defined above. R ^{3 '} represents one of the following groups (i) to (xxii).
(i) group-(W) o-NR ^{4 '} R ^5'
(W and o are the same as above. R ^{4 ′} represents a hydrogen atom, a C1-6 alkyl group or a phenylcarbamoyl group [wherein a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or substituted on the phenyl ring And at least one of a group selected from the group consisting of unsubstituted C1-6 alkoxy groups may be substituted] R ^{5 '} is a phenyl C1-6 alkoxycarbonyl group [on the phenyl ring, At least one selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted; 6 alkenylcarbonyl group [on the phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1 group; At least one group selected from the group consisting of 6 alkoxy groups may be substituted; phenyl C2-6 alkenyl group [on the phenyl ring, a halogen atom, halogen substituted or unsubstituted C1-6 alkyl Group and at least one group selected from the group consisting of halogen substituted or unsubstituted C1-6 alkoxy group may be substituted; pipedyryl C1-6 alkyl group [at least one on a piperidine ring (In the phenyl ring, at least one of a group selected from the group consisting of halogen atoms, halogen-substituted or unsubstituted C.sub.1-6 alkyl groups and halogen-substituted or unsubstituted C.sub.1-6 alkoxy groups is substituted. Optionally substituted); phenyl C1-6 alkyl group [wherein at least one phenyl group (phenyl ring on the phenyl ring (phenyl ring In which at least one of a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group may be substituted) Benzofuryl C1-6 alkyl group [wherein at least one halogen-substituted or unsubstituted C1-6 alkyl group may be substituted on the benzofuran ring]; piperidyl carbonyl C1 6 alkyl groups [in the piperidine ring, at least one phenoxy group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group At least one of the groups selected from the group consisting of

[R ^{6 ′} represents a C1 to ⁶ alkyl group; a phenyl group (on a phenyl ring, a C 1 to 4 alkylenedioxy group, a cyano group, a nitro group, an amino group sometimes having a C 1 to ⁶ alkyl group as a substituent An amino-substituted sulfonyl group which may have a C1-6 alkyl group as a substituent, a C1-6 alkoxycarbonyl group, a C1-6 alkylthio group, a phenoxy group, a phenyl C1-6 alkoxy group, a pyrrolidinyl group [a pyrrolidine ring And at least one oxo group may be substituted], imidazolyl group, isoxazolyl group, oxazolyl group, phenyl C1-6 alkyl group, phenyl group, amino C1 having a C1-6 alkyl group as a substituent To 6 alkyl group, pyrrolidinyl C1-6 alkoxy group, halogen atom, halogen substituted or unsubstituted Cア ル キ ル 6 alkyl group and at least one group selected from the group consisting of halogen substituted or unsubstituted C1-6 alkoxy group may be substituted; phenyl C1-6 alkoxycarbonyl group (on the phenyl ring) And at least one group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group may be substituted); 6 alkyl group (in the benzofuran ring, at least one of a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group is substituted Benzofuryl C 2-6 alkenyl group (on the benzofuran ring, a halogen atom, halogen Or at least one of a group selected from the group consisting of an unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted; phenoxy C1-6 alkyl group (phenyl At least one selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted on the ring) A thiazolyl C1-6 alkyl group (on the thiazolyl ring, at least one phenyl group [on a phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6; At least one of a group selected from the group consisting of an alkoxy group may be substituted]; phenyl C 1 to 6 alkyl groups (on the phenyl ring [phenyl group on the phenyl ring, halogen atoms, halogen substituted or unsubstituted C1 to 6 alkyl groups and halogen substituted or unsubstituted C1 to 6 alkoxy groups; Selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group, and a halogen-substituted or unsubstituted C1-6 alkoxy group; At least one of the groups may be substituted); pyridyl C1-6 alkyl group (on the pyridine ring at least one phenyl group [on the phenyl ring a halogen atom, halogen substituted or unsubstituted C1 -6 alkyl group and at least one kind of group selected from the group consisting of halogen substituted or unsubstituted C1-6 alkoxy group may be substituted] C1-6 alkoxycarbonyl group; benzoyl group (on the phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group At least one group selected from the group consisting of: a phenylcarbamoyl group (on the phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted group; At least one of a group selected from the group consisting of a C1-6 alkoxy group may be substituted); benzothienyl group; benzothienyl C1-6 alkyl group (at least one halogen on a benzothiophene ring) An atom may be substituted); indolyl C1-6 alkyl group (on the indole ring, halogen At least one group selected from the group consisting of aryl, halogen substituted or unsubstituted C.sub.1-6 alkyl group and halogen substituted or unsubstituted C.sub.1-6 alkoxy group); 4H-1, 3-benzodioxynyl group (at least one halogen atom may be substituted on the 4H-1,3-benzodioxin ring); naphthyl group; quinolyl group; benzothiazolyl group (on benzothiazole ring) Is optionally substituted by at least one C.sub.1-6 alkyl group; 2,3-dihydro-1H-indenyl group (on the 2,3-dihydro-1H-indan ring, at least one oxo). Group may be substituted); 9H-fluorenyl group or phenyl C2-6 alkenyl group (on the phenyl ring, a halogen atom, halogen substituted or unsubstituted C1-6 alkyl And it represents at least one may be substituted) groups selected from the group consisting of C1~6 alkoxy group a halogen substituted or unsubstituted. ]
Indicates );
(ii) group

(W and o are the same as above. The dotted line indicates that it may be a double bond. When the dotted line shows a double bond, only R ^{8 ′} is substituted. R ^{7 ′} is hydrogen R ^{8 ′} represents an atom, a hydroxyl group, a C 1 to 6 alkoxy group or a phenyl group [a halogen may be substituted on the phenyl ring], and R ^{8 ′} represents a group of any one of the following (1) to (63) Show.
(1) Phenyl C1-6 alkoxy substituted C1-6 alkyl group (in the phenyl ring, C1-4 alkylenedioxy group, halogen atom, cyano group, phenyl group, phenyl C1-6 alkoxy group, phenyl C2-6 alkenyl At least one group selected from the group consisting of a group, a phenoxy group, a C1-6 alkylthio group, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group May)
(2) phenyl C1-6 alkoxy group (on the phenyl ring, cyano group, phenyl group, C1-6 alkoxycarbonyl group, phenoxy group, C1-6 alkylthio group, halogen atom, halogen substituted or unsubstituted C1-6 At least one of a group selected from the group consisting of an alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted);
(3) phenyl C2-6 alkenyloxy group (on the phenyl ring, selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group At least one of the groups may be substituted);
(4) Group-(W) o-NR ^{9 '} R ^10'
(W and o are the same as above.
R ^{9 ′} and R ^{10 ′} are the same or different and are a hydrogen atom; a C1-6 alkyl group which may have a hydroxyl group as a substituent; C1-6 alkanoyl group; C1-6 alkoxycarbonyl group; phenyl C1-6 alkoxy A carbonyl group [in which at least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group is substituted on a phenyl ring; Phenyl group [in the phenyl ring, as a substituent, a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group, a halogen-substituted or unsubstituted C1-6 alkoxy group, a substituent, a C1 to C6 alkyl group; An amino group which may have a group selected from the group consisting of 6 alkanoyl groups and a C1-6 alkyl group, a C1-6 alkoxycarbonyl group A phenyl group, a phenoxy group (on the phenyl ring, at least one of a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group Species may be substituted), an aminosulfonyl group, a 1,2,3,4-tetrahydroquinolyl group (on the 1,2,3,4-tetrahydroquinoline ring, at least one oxo group may be substituted as a substituent). (Optionally substituted), C1-6 alkylsulfonyl group, C3-8 cycloalkyl group, nitro group, cyano group, C1-6 alkylthio group, phenylsulfonyl group (on halogen ring, halogen atom, halogen substituted Or at least one group selected from the group consisting of an unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group And may be), hydroxy-substituted C1~6 alkyl group and group

(W ₁ is the same as above. R ^{11 ′} and R ^{12 ′} are the same or different and each represents a C _{1 to 6} alkoxy group.) At least one of the groups selected from the group consisting of A phenyl C1-6 alkyl group [in the phenyl ring, a C1-4 alkylenedioxy group as a substituent, a phenyl group (in the phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group, At least one group selected from the group consisting of halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted), a group -N ( ^{R11A '} ) ^R12A' ( ^{R11A '} and ^{R12A) '} Are the same or different and each represents a hydrogen atom, a C1-6 alkyl group or a phenyl group. R11A ^' and ^{R12A '} , together with the adjacent nitrogen atoms, are either without or via a nitrogen atom, an oxygen atom or a sulfur atom 5 to 7 members connected to each other A saturated heterocyclic ring may be formed, phenoxy group (on the phenyl ring, from a group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group At least one selected group may be substituted), phenyl C1-6 alkoxy group, amino group substituted C1-6 alkoxy group which may have C1-6 alkyl group as a substituent, halogen atom, halogen At least one selected from the group consisting of a substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-10 alkoxy group may be substituted]; a benzofuryl C1-6 alkyl group [ On the benzofuran ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alcohol. At least one of a group selected from the group consisting of a substituent group; a phenylsulfonyl group [on a phenyl ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group, a halogen substituted Or at least one of a group selected from the group consisting of an unsubstituted C1-6 alkoxy group and a C1-4 alkylenedioxy group may be substituted]; phenoxycarbonyl group [a halogen atom on a phenyl ring And at least one selected from the group consisting of a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted]; phenyl C2-6 alkenyl Group [on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy. At least one group selected from the group consisting of groups may be substituted]; C1-6 alkoxy substituted C1-6 alkyl group; C2-6 alkenyl group; C1-6 alkoxy substituted C2-6 alkanoyl group; C3-8 cycloalkyl substituted C1-6 alkyl group; phenoxy C1-6 alkyl group [on the phenyl ring, halogen atom, halogen substituted or unsubstituted C1-6 alkyl group and halogen substituted or unsubstituted C1-6 alkoxy Benzoyl group [in the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or not substituted group]; At least one of a group selected from the group consisting of a substituted C1-6 alkoxy group may be substituted]; phenylcarbamoyl group [fe At least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group on the ring Pyridyl group; pyridyl C1-6 alkyl group; imidazolyl C1-6 alkyl group; 1,2,3,4-tetrahydroquinolyl group [1,2,3,4-tetrahydroquinoline ring, substituents And at least one group selected from the group consisting of oxo group and C1-6 alkyl group may be substituted]; quinolyl group; indolyl group; amino having C1-6 alkyl group as a substituent Group: indazolyl group; naphthyl group; C3-8 cycloalkyl group; amino substituted C1-6 alkyl group which may have C1-6 alkyl group as a substituent; Substituted C1~6 alkyl group; furyl substituted C1~6 alkyl group; group

[RR is a phenyl group (on the phenyl ring, at least one of the groups selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group. The species is optionally substituted). Or a piperazinyl substituted C1-6 alkyl group [in the piperazine ring, at least one phenyl group as a substituent (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or At least one member selected from the group consisting of unsubstituted C1-6 alkoxy groups may be substituted).
R ^{9 ′} and R ^{10 ′} are, together with adjacent nitrogen atoms, bonded to each other via or without a nitrogen atom, an oxygen atom or a sulfur atom, and a 1,2,3,4-tetrahydroisoquinolyl group, an isoindolyl group or It may form a 5- to 7-membered saturated heterocyclic ring. On the heterocycle, a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group, a halogen-substituted or unsubstituted C1-6 alkoxy group, a phenyl group [on the phenyl ring, a phenyl group, a halogen atom, a halogen At least one of a group selected from the group consisting of a substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group may be substituted, a benzoyl group [on a phenyl ring At least one of a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group may be substituted], pyridyl C1-6 alkyl group, C3-8 cycloalkyl group, phenyl C1-6 alkyl group [on the phenyl ring, a C1 to 4 alkylenedioxy group, a halogen At least one selected from the group consisting of an atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group], piperidyl C1-6 Alkyl group, piperidyl group, phenyl C1-6 alkoxy group [on the phenyl ring, selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group At least one of the above-mentioned groups may be substituted], phenoxy group [in the phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy] Group may be substituted by at least one group selected from the group consisting of At least one group selected from the group consisting of a gen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group], C1 to C6 Alkyl group and phenyl C1-6 alkyl group [on the phenyl ring, a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group At least one group selected from the group consisting of: an amino group which may be substituted by at least one group selected from the group consisting of: benzoxazolyl group, phenyl C 2-6 alkenyl group (on phenyl ring A group selected from the group consisting of halogen atoms, halogen-substituted or unsubstituted C.sub.1-6 alkyl groups and halogen-substituted or unsubstituted C.sub.1-6 alkoxy groups; And at least one group selected from the group consisting of benzimidazolyl groups may be substituted);
(5) phenyl C1-6 alkyl group (a halogen atom on a phenyl ring, a halogen group on a phenyl ring (a phenyl ring, a halogen atom substituted or unsubstituted C1 to 6 alkyl group and a halogen substituted or unsubstituted C1 At least one group selected from the group consisting of -6 alkoxy groups may be substituted), halogen substituted or unsubstituted C1-6 alkyl group and halogen substituted or unsubstituted C1-6 alkoxy group At least one of the groups selected from the group may be substituted);
(6) a carbamoyloxy group (on the amino group, a C1-6 alkyl group and a phenyl group [a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1 -At least one group selected from the group consisting of-6 alkoxy groups may be substituted] at least one group selected from the group consisting of
(7) carbamoyloxy substituted C1-6 alkyl group (on the amino group, C1-6 alkyl group, phenyl C1-6 alkyl group, C3-8 cycloalkyl group, naphthyl group, 2,3-dihydro-1H-indenyl Group, 2,3-dihydrobenzofuryl group and phenyl group [in the phenyl ring, C1-4 alkylenedioxy group, cyano group, phenoxy group, C1-6 alkylthio group, C1-6 alkanoyl group, phenyl group, phenyl group Even if at least one group selected from the group consisting of a C1-6 alkyl group, a halogen atom, a halogen substituted or unsubstituted C1-10 alkyl group and a halogen substituted or unsubstituted C1-10 alkoxy group is substituted At least one of the groups selected from the group consisting of
(8) phenoxy C1-6 alkyl group (a halogen atom on the phenyl ring; C1 -4 alkylenedioxy group; C1 -6 alkoxycarbonyl group; phenyl group; phenoxy group; pyrrolyl group; benzothiazolyl group; 4-triazolyl group, imidazolyl group, isoxazolyl group, benzoxazolyl group, benzotriazolyl group, cyano group, nitro group, C2-6 alkenyl group, C1-6 alkanoyl group, C1-6 alkoxycarbonyl substituted C1-6 alkyl group; Cl to 6 alkanoyl substituted Cl to 6 alkyl radical; group ^{-N (R 11B ') R 12B} ' (R 11B ' and R ^12B' are the same or different and represent a hydrogen atom, Cl to 6 alkyl, C1 to .R ^{11B 'and} R ^12B' indicate the 6 alkanoyl group or a phenyl group, together with the adjacent nitrogen atom, a nitrogen atom, an oxygen atom or a sulfur atom Or a 5- to 7-membered saturated heterocyclic ring may be formed on the heterocyclic ring via a C1-6 alkoxycarbonyl group or an amino group [a phenyl group At least one of a group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group is substituted on the phenyl ring And at least one group selected from the group consisting of C.sub.1-6 alkyl groups and at least one group selected from the group consisting of C.sub.1-6 alkyl groups may optionally be substituted); C1-6 alkoxy group; phenyl C1-6 alkyl group; C1-6 alkylthio group; C3-8 cycloalkyl group; halogen substituted or unsubstituted C1-6 alkyl group and halogen substituted or not At least one may be substituted for a group selected from the group consisting of C1~10 alkoxy group conversion);
(9) tetrahydropyranyloxy C1-6 alkyl group;
(10) a hydroxyl group substituted C1 to 6 alkyl group;
(11) furyl C1-6 alkoxy-substituted C1-6 alkyl group (wherein at least one C1-6 alkoxycarbonyl group may be substituted on the furan ring);
(12) Tetrazolyl C1-6 alkoxy substituted C1-6 alkyl group (on tetrazole ring, a phenyl group (a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted And at least one group selected from the group consisting of C1-6 alkoxy groups may be substituted), and selected from the group consisting of phenyl C1-6 alkyl groups and C3-8 cycloalkyl C1-6 alkyl groups A substituted group may be substituted);
(13) isoxazolyl C1-6 alkoxy-substituted C1-6 alkyl group (at least one C1-6 alkyl group may be substituted on the isoxazole ring);
(14) benzothienyl C.sub.1-6 alkoxy-substituted C.sub.1-6 alkyl group (on the benzothiophene ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group At least one of the groups selected from the group consisting of
(15) 1,3,4-oxadiazolyl C.sub.1-6 alkoxy-substituted C.sub.1-6 alkyl group (on the 1,3,4-oxadiazole ring, a phenyl group [on the phenyl ring, a halogen atom, halogen-substituted or At least one of a group selected from the group consisting of an unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted);
(16) C2-6 alkynyloxy substituted C1-6 alkyl group;
(17) Naphthyl C1-6 alkoxy substituted C1-6 alkyl group;
(18) 1,2,4-oxadiazolyl C1-6 alkoxy-substituted C1-6 alkyl group [a phenyl group may be substituted on the 1,2,4-oxadiazole ring];
(19) Pyridyl C.sub.1-6 alkoxy-substituted C.sub.1-6 alkyl group [in the pyridine ring, a group consisting of a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group At least one of the selected groups may be substituted];
(20) thiazolyl C1-6 alkoxy substituted C1-6 alkyl group [wherein a phenyl group (a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted on a phenyl ring Or at least one group selected from the group consisting of C1-6 alkoxy groups may be substituted) and at least one group selected from the group consisting of C1-6 alkyl groups may be substituted ];
(21) 1,2,3,4-tetrahydronaphthyl C1-6 alkoxy-substituted C1-6 alkyl group [1,2,3,4-tetrahydronaphthalene ring, at least one C1-6 alkyl group is substituted May be
(22) carbamoyl C1-6 alkoxy substituted C1-6 alkyl group [C3-8 cycloalkyl group and phenyl group on the amino group (halogen atom, halogen substituted or unsubstituted C1-6 alkyl on the phenyl ring At least one group selected from the group consisting of groups and at least one group selected from the group consisting of halogen-substituted or unsubstituted C1-6 alkoxy groups is substituted Also good];
(23) benzofuryl C1-6 alkoxy-substituted C1-6 alkyl group [at least one cyano group may be substituted on the benzofuran ring];
(24) Benzofuryl C1-6 alkyl group [in the benzofuran ring, a group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group At least one of may be substituted];
(25) phenoxy group [in which at least one group selected from the group consisting of phenyl C1-6 alkoxy group, C3-8 cycloalkyl group, C7-10 alkoxy group and phenoxy group is substituted on the phenyl ring Shall be present];
(26) a naphthyloxy group;
(27) 2,3-dihydrobenzofuryloxy group [in the 2,3-dihydrobenzofuran ring, at least one oxo group may be substituted];
(28) a benzothiazolyloxy group [at least one C1-6 alkyl group may be substituted on the benzothiazole ring];
(29) 1,2,3,4-tetrahydronaphthyloxy group [at least one oxo group may be substituted on the 1,2,3,4-tetrahydronaphthalene ring];
(30) dibenzofuryloxy group;
(31) quinolyloxy group;
(32) furyl C1-6 alkoxy group [optionally, at least one C1-6 alkoxycarbonyl group may be substituted on the furan ring];
(33) Tetrazolyl C1-6 alkoxy group [in which at least one group selected from the group consisting of phenyl C1-6 alkyl group and C3-8 cycloalkyl C1-6 alkyl group is substituted on the tetrazole ring Also good];
(34) 1,2,4-oxadiazolyl C.sub.1-6 alkoxy group [a phenyl group (a halogen atom, a halogen-substituted or unsubstituted C.sub.1 substituted on the phenyl ring, and a phenyl group on the 1,2,4-oxadiazole ring. At least one of a group selected from the group consisting of 6 alkyl groups and halogen-substituted or unsubstituted C1-6 alkoxy groups may be substituted);
(35) benzothienyl C1-6 alkoxy group [at least one halogen atom may be substituted on the benzothiophene ring];
(36) isoxazolyl C1-6 alkoxy group [in the isoxazole ring, at least one C1-6 alkyl group may be substituted];
(37) 1,3,4-oxadiazolyl C.sub.1-6 alkoxy group [in the case of at least one phenyl group on the 1,3,4-oxadiazole ring (on the phenyl ring at least one C.sub.1-6 group. An alkyl group may be substituted) may be substituted];
(38) naphthyl C1-6 alkoxy group;
(39) a pyridyl C1-6 alkoxy group (on the pyridine ring, at least one halogen-substituted or unsubstituted C1-6 alkyl group may be substituted);
(40) thiazolyl C1-6 alkoxy group [in which at least one phenyl group (a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted group on the phenyl ring At least one of a group selected from the group consisting of a C1-6 alkoxy group may be substituted);
(41) 1,2,3,4-tetrahydronaphthyl C1-6 alkoxy group (1,2,3,4 tetrahydronaphthalene ring may be substituted by at least one C1-6 alkyl group );
(42) a phenoxy C1-6 alkoxy group (a group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group on the phenyl ring At least one of which may be substituted);
(43) carbamoyl C1-6 alkoxy group [on an amino group, a C3-8 cycloalkyl group and a phenyl group (on a phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or At least one group selected from the group consisting of at least one group selected from the group consisting of unsubstituted C1-6 alkoxy groups may be substituted];
(44) benzofuryl C1-6 alkoxy group (at least one cyano group may be substituted on the benzofuran ring);
(45) Naphthyloxy oxy C1-6 alkyl group (wherein at least one C1-6 alkoxy group may be substituted on the naphthalene ring);
(46) benzothiazolyloxy C1-6 alkyl group (on the benzothiazole ring, at least one C1-6 alkyl group may be substituted);
(47) quinolyloxy C1-6 alkyl group (on the quinoline ring, at least one C1-6 alkyl group may be substituted);
(48) 2,3-Dihydrobenzofuryloxy C1-6 alkyl group (wherein at least one group selected from the group consisting of a C1-6 alkyl group and an oxo group is substituted on the 2,3-dihydrobenzofuran ring May));
(49) 1,2,3,4-tetrahydronaphthyloxy C1-6 alkyl group (in the 1,2,3,4-tetrahydronaphthalene ring, at least one oxo group may be substituted);
(50) 2,3-dihydro-1H-indenyloxy C1-6 alkyl group (wherein at least one oxo group may be substituted on 2,3-dihydro-1H-indene ring);
(51) Benzoxathiolanyloxy C1-6 alkyl group (wherein at least one oxo group may be substituted on the benzooxathiolane ring);
(52) isoquinolyloxy C1-6 alkyl group;
(53) pyridyloxy C1-6 alkyl group;
(54) dibenzofuryloxy C1-6 alkyl group;
(55) 2H-1-benzopyranyloxy C1-6 alkyl group (in the 2H-1-benzopyran ring, at least one oxo group may be substituted);
(56) benzisoxazolyloxy C1-6 alkyl group;
(57) benzofurazanyloxy C1-6 alkyl group;
(58) quinoxalyloxy C1-6 alkyl group;
(59) C1-6 alkoxy C1-6 alkoxy substituted C1-6 alkyl group;
(60) thienyl C1-6 alkoxy-substituted C1-6 alkyl group (wherein at least one halogen atom may be substituted on the thiophene ring);
(61) phenyl C2-6 alkenyloxy substituted C1-6 alkyl group (containing a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group on the phenyl ring At least one of the groups selected from the group may be substituted);
(62) quinolyl C1-6 alkoxy substituted C1-6 alkyl group;
(63) piperidylcarbonyl C1-6 alkoxy substituted C1-6 alkyl group;
Also, R ^{7 ′} and R ^{8 ′} may be taken together to form a group CC (R ^{29 ′} ) (R ^{30 ′} ). Here, R ^{29 ′} and R ^{30 ′} are the same or different and each is a hydrogen atom, a C 1-6 alkyl group or a phenyl group [on a phenyl ring, a halogen atom, a halogen substituted or unsubstituted C 1-6 alkyl group and a halogen At least one group selected from the group consisting of a substituted or unsubstituted C1-6 alkoxy group may be substituted. );
(iii) group

(W ₁ and o are the same as above. R ^{13 ′} is a 2,3-dihydro-1H-indenyl group; a benzothienyl group; a phenyl C 2-10 alkenyl group [on a phenyl ring, a halogen atom, a C 1-4 alkyl group Dioxy oxy group, C1-6 alkylthio group, benzoyl group, cyano group, nitro group, C2-6 alkanoyloxy group, amino group which may have C1-6 alkyl group as a substituent, hydroxyl group, phenyl C1-6 alkoxy group And at least one group selected from the group consisting of phenoxy group, halogen-substituted or unsubstituted C1-6 alkyl group and halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted]; naphthyl C2 -6 alkenyl group; benzofuryl C1-6 alkyl group [in the benzofuran ring, a halogen atom, halogen substituted or unplaced At least one of a group selected from the group consisting of C1-6 alkyl groups and halogen substituted or unsubstituted C1-6 alkoxy groups; and benzothienyl C2-6 alkenyl group; benzothiazolyl C2 6 alkenyl group [at least one C1-6 alkyl group may be substituted on the benzothiazole ring]; phenyl C1-6 alkyl group [on the phenyl ring a piperidinyl group (on the piperidine ring At least one phenoxy group [in the phenyl ring, at least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group; 1) may be substituted), a phenyl group (on the phenyl ring, a halogen atom, a halogen) At least one group selected from the group consisting of a substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group is substituted, and a phenoxy group (on the phenyl ring) At least one of a group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group) At least one of the groups selected from the group consisting of: diphenyl C.sub.1-6 alkyl group [on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen; At least one of a group selected from the group consisting of a substituted or unsubstituted C1-6 alkoxy group may be substituted]; Alkyl group [on the phenyl ring, at least one of the groups selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group Species may be substituted]; C1-6 alkyl group, C1-6 alkoxycarbonyl group and phenyl C1-6 alkyl group [phenyl group (on halogen ring, halogen atom on phenyl ring, halogen substituted Or at least one of a group selected from the group consisting of an unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted), a halogen atom, a halogen-substituted or an unsubstituted group At least one group selected from the group consisting of a C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group An amino group which may be substituted by at least one group selected from the group consisting of one group may be substituted; a C1-6 alkyl group and a phenyl group (a halogen atom on a phenyl ring, At least one group selected from the group consisting of a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted) Amino C1-6 alkyl group which may be substituted; benzofuryl C2-6 alkenyl group [wherein on the benzofuran ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or not substituted At least one group selected from the group consisting of substituted C1-6 alkoxy groups may be substituted]; piperidyl group [on a piperidine ring At least one phenyl C 2-6 alkenyl group (on the phenyl ring, selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group At least one kind of the above groups may be substituted); ferrocene substituted C.sub.1-6 alkyl group, indolyl C.sub.1-6 alkyl group (on indole ring, at least one halogen atom) May be substituted); phenyl C2-6 alkynyl group; phenyl group [C1 to 4 alkylenedioxy group, phenyl group, C1 to 6 alkoxycarbonyl group, hydroxyl group and phenoxy group (phenyl ring Above, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1 6) at least one group selected from the group consisting of alkoxy groups may be substituted), at least one group selected from the group consisting of) is substituted; benzofuryl group [benzofuran ring Above, at least one of a group selected from the group consisting of a halogen atom and a C1-6 alkyl group may be substituted); a benzothiazolinyl group [in the benzothiazoline ring, at least one of Oxo group may be substituted !; benzothienyl group [at least one halogen atom may be substituted on the benzothiophene ring]; naphthyl group; 1,2,3,4-tetrahydroquino A lyl group [at least one of a group selected from the group consisting of an oxo group and a C1-6 alkyl group may be substituted on the 1,2,3,4-tetrahydroquinoline ring]; A zoisoxazolyl group; a 2,3-dihydrobenzofuryl group; a 1,2-dihydroquinolyl group [at least one oxo group may be substituted on the 1,2-dihydroquinoline ring] 1,2,3,4-tetrahydroquinazolinyl group [1,2,3,4-tetrahydroquinazoline ring, on the ring, at least one member selected from the group consisting of oxo group and C1-6 alkyl group; May be substituted]; benzocycloheptyl group; phenoxy C1-6 alkyl group [in the phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-C6 alkyl group] At least one of a group selected from the group consisting of 6 alkoxy groups may be substituted]; benzothienyl substituted C.sub.1-6 alkyl group [a few on the benzothiophene ring At least one halogen atom may be contained); naphthyl-substituted C1-6 alkyl group [wherein at least one C1-6 alkoxy group may be substituted on the naphthalene ring]; pyridyl substituted C1-6 alkyl group [at least one halogen atom may be substituted on a pyridine ring]; furyl-substituted C1-6 alkyl group [at least one nitro group is substituted on a furan ring Thienyl-substituted C1-6 alkyl group [at least one halogen atom may be substituted on the thiophene ring]; thiazolyl-substituted C1-6 alkyl group [on the thiazole ring C1 To 6 alkyl group and a phenyl group (on the phenyl ring, at least one selected from the group consisting of a halogen atom and a halogen substituted or unsubstituted C.sub.1-6 alkyl group. And at least one group selected from the group consisting of is optionally substituted); tetrazolyl-substituted C.sub.1-6 alkyl group [in the tetrazole ring, at least one C.sub.1-6 group; Alkyl group may be substituted; isoxazolyl substituted C1-6 alkyl group [at least one C1-6 alkyl group may be substituted on the isoxazole ring]; 1,2,4- Oxadiazolyl substituted C1-6 alkyl group [in the 1,2,4-oxadiazole ring, at least one phenyl group (C1-6 alkyl group may be substituted on the phenyl ring) It may be substituted] or a benzofurazinyl substituted C1-6 alkyl group is shown. );
(iv) group

(R ^{14 ′} may be substituted with a C1 to 6 alkyl group at the N position of a phenylamino group [phenylamino group, and at least one halogen-substituted or unsubstituted group on the phenyl ring of the phenylamino group The C 1 to C 6 alkoxy group may be substituted); the piperidyl group [a phenoxy group on the piperidine ring (a halogen substituted or unsubstituted C 1 to C 6 alkoxy group may be substituted on the phenyl ring And an amino group (on the amino group, a C1-6 alkyl group as a substituent and a phenyl group [a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted on a phenyl ring And at least one group selected from the group consisting of C1-6 alkoxy groups may be substituted]; at least one group selected from the group consisting of At least one group selected from the group consisting of optionally substituted) may be substituted]; piperazinyl group [C.sub.1-6 alkoxycarbonyl group, phenyl C.sub.1-6 alkyl group on piperazine ring (On the phenyl ring, at least one of a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group is substituted (Optional), phenyl C2-6 alkenyl group (on the phenyl ring, selected from the group consisting of halogen atom, halogen substituted or unsubstituted C1-6 alkyl group and halogen substituted or unsubstituted C1-6 alkoxy group And at least one group may be substituted) and benzoyl group (on the phenyl ring, a halogen atom, halogen substituted or not, At least one group selected from the group consisting of substituted C1-6 alkyl groups and at least one group selected from the group consisting of halogen-substituted or unsubstituted C1-6 alkoxy groups) A phenyl group (on the phenyl ring, selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group At least one of the above-mentioned groups may be substituted); homopiperazinyl group [in the homopiperazine ring, a C.sub.1-6 alkoxycarbonyl group and a phenyl C.sub.1-6 alkyl group (on the phenyl ring, a halogen atom, a halogen; It is selected from the group consisting of a substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group Or at least one group selected from the group consisting of at least one group may be substituted) or a phenoxy group [on the phenyl ring, halogen-substituted or unsubstituted C1 to C6] At least one group selected from the group consisting of an alkoxy group and a phenoxy substituted phenyl group (wherein at least one halogen substituted or unsubstituted C1-6 alkoxy group may be substituted on the phenyl ring) is May be substituted]. );
(v) group

(R ^{13 ′} is the same as above. The dotted line indicates that it may be a double bond);
(vi) homopiperazinyl group (C1-6 alkoxycarbonyl group on homopiperazine ring; phenyl C1-6 alkyl group [on halogen ring, halogen atom, halogen substituted or unsubstituted C1-6 alkyl group and halogen substituted Or at least one group selected from the group consisting of unsubstituted C1-6 alkoxy groups may be substituted; phenyl group [on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1 group, 6 alkyl group and at least one selected from the group consisting of halogen substituted or unsubstituted C1-6 alkoxy group may be substituted]; phenyl C1-6 alkoxycarbonyl group [on the phenyl ring, A halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkyl group At least one group selected from the group consisting of alkoxy group may be substituted; phenylcarbamoyl group [in the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted Or at least one group selected from the group consisting of unsubstituted C.sub.1-6 alkoxy groups may be substituted; phenyl C.sub.2-6 alkenyl group [on the phenyl ring, a halogen atom, halogen substituted or not, or At least one of a group selected from the group consisting of a substituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group may be substituted; and a benzoyl group [on the phenyl ring, a halogen From an atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group That at least one group of at least one kind selected from the group consisting of] may be substituted groups may be substituted selected from a group);
(vii) group

(Wherein, R ^{19 ′} represents a C1-6 alkoxy group. R ^{20 ′} represents a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group, and a halogen-substituted or non-substituted phenyl group on a phenyl group [phenyl ring At least one group selected from the group consisting of substituted C1-6 alkoxy groups may be substituted.
(viii) group -CHR ^{20 '} R ^21'
(R ^{20 ′} is the same as above. R ^{21 ′} represents an amino group which may have a C 1-6 alkyl group as a substituent.);
(ix) 1,2,3,4-tetrahydroisoquinolyl group (1,2,3,4-tetrahydroisoquinoline ring on at least one amino group [amino group on phenyl C1 -6 alkyl Group (on the phenyl ring, at least one of a group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group is substituted) And at least one group selected from the group consisting of C1-6 alkyl groups may be substituted);
(x) an oxazolyl group (a group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group on the phenyl ring [phenyl group on the oxazole ring At least one of the selected groups may be substituted], C1-6 alkyl group and piperidyl group [in the piperidine ring, at least one phenoxy group (on the phenyl ring, a halogen atom, halogen At least one of a group selected from the group consisting of a substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group may be substituted or substituted) Optionally substituted], at least one of the groups selected from the group: optionally substituted);
(xi) isoindolinyl group (on the isoindoline ring, at least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group May be substituted);
(xii) thiazolyl group (on thiazole ring, phenoxy C1-6 alkyl group [on phenyl ring, halogen atom, halogen substituted or unsubstituted C1-6 alkyl group and halogen substituted or unsubstituted C1-6 alkoxy group At least one group selected from the group consisting of: a phenyl group [wherein a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted group on the phenyl ring At least one of a group selected from the group consisting of a C1-6 alkoxy group may be substituted; a phenyl C1-6 alkyl group [on a phenyl ring, a halogen atom, a halogen substituted or an unsubstituted C1-6, At least one of the groups selected from the group consisting of alkyl groups and halogen substituted or unsubstituted C1-6 alkoxy groups is substituted It may be]; group ^{_{- (W 1) oNR 31 '}} R 32' [W 1 and o are as defined above .R ^{31 'and} R ^32' are the same or different, a hydrogen atom, Cl to 6 alkyl Group, a phenyl group (on the phenyl ring, at least one of a group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group is substituted Or a phenyl C1-6 alkyl group (on the phenyl ring, selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group At least one of the above-mentioned groups may be substituted)]; Piperazinyl [in the piperazine ring at least one phenyl group (on the phenyl ring a halogen atom At least one of a group selected from the group consisting of a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted) A piperidyl group [on a piperidine ring, a phenoxy group (on a phenyl ring, selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group; And at least one group selected from the group consisting of phenyl C1-6 alkyl group may be substituted] and phenoxy group [on the phenyl ring, A group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group Ri at least one may be at least one substituted group selected from the group consisting of and may have] substituted group selected);
(xiii) hydroxyl group-substituted C1-6 alkyl group;
(xiv) oxazolyl C1-6 alkyl group (on the oxazole ring, at least one phenyl group [on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted At least one of a group selected from the group consisting of a C1-6 alkoxy group may be substituted];
(xv) isoxazolyl group (on the isoxazoline ring at least one phenyl group [on the phenyl ring a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 At least one of a group selected from the group consisting of an alkoxy group may be substituted];
(xvi) benzoxazolyl group (on the benzoxazole ring, at least one halogen atom may be substituted);
(xvii) phenylthio group (on the phenyl ring, at least one group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group May be substituted);
(xviii) benzoimidazolyl group (on a benzimidazole ring, a halogen atom and a phenyl C1-6 alkyl group [on a phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted At least one kind of groups selected from the group consisting of C1-6 alkoxy groups may be substituted] and at least one kind of groups selected from the group: optionally substituted);
(xiv) a pyrrolidinyl group (on the pyrrolidine ring at least one amino group [on the amino group a C1-6 alkyl group and a phenyl group (on the phenyl ring a halogen atom, halogen-substituted or unsubstituted C1 At least one group selected from the group consisting of 6 alkyl group and at least one group selected from the group consisting of halogen substituted or unsubstituted C1-6 alkoxy group) May be substituted));
(xx) phenylsulfonyl group (on the phenyl ring, at least one of a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group Species may be substituted);
(xxi) imidazolyl group (on the imidazole ring, at least one phenyl group [on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy At least one of the groups selected from the group consisting of groups may be substituted);
(xxii) a phenylsulfinyl group (on the phenyl ring, at least one of a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group Species may be substituted);

(S) imidazolyl group (on the imidazole ring, at least one of a group selected from the group consisting of a halogen atom and a nitro group may be substituted);

(T) Isoindolinyloxy group (C1-6 alkoxycarbonyl group on phenyl group, phenyl C1-6 alkyl group on phenyl group (benzofuryl group, halogen atom, halogen substituted or unsubstituted C1 group on phenyl ring) 6 alkyl group and at least one group selected from the group consisting of halogen substituted or unsubstituted C1-6 alkoxy group may be substituted], phenyl C2-6 alkenyl group [on the phenyl ring, halogen At least one selected from the group consisting of an atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group], furyl C1 to C6 An alkyl group [on the furan ring, at least one phenyl group (on the phenyl ring, a halogen atom, halogen substitution Or at least one of a group selected from the group consisting of an unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted) A pyridyl C1-6 alkyl group [a pyridine ring, a furyl group and a phenyl group (a phenyl atom, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 At least one group selected from the group consisting of alkoxy group, at least one group selected from the group consisting of alkoxy group may be substituted], benzofuryl C1-6 alkyl group [ On the benzofuran ring, from a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group And at least one kind of groups selected from the group consisting of the following groups], benzothienyl C.sub.1-6 alkyl group [at least one halogen atom may be substituted on the benzothiophene ring], Benzofuryl C2-6 alkenyl group [in the benzofuran ring, at least one of the groups selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group Species may be substituted], a thiazolyl group [in which at least one phenyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted At least one of a group selected from the group consisting of unsubstituted C.sub.1-6 alkoxy groups may be substituted) And phenoxy C1-6 alkyl group [on the phenyl ring, selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group At least one kind of the group selected from the group consisting of at least one kind of the group may be substituted);

(U) benzothiazolidinyloxy group (on the benzothiazolidine ring, an oxo group and a phenyl C1 to 6 alkyl group [on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1 to 6 alkyl group and a halogen At least one group selected from the group consisting of a substituted or unsubstituted C1-6 alkoxy group may be substituted] at least one group selected from the group consisting of ;

(V) indolyloxy group (in the indole ring, at least one phenyl C.sub.1-6 alkyl group [in the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or not substituted. At least one group selected from the group consisting of substituted C1-6 alkoxy groups may be substituted);

(W) a pyrrolidinyl group (on the pyrrolidine ring at least one amino group [on the amino group a C1 to 6 alkyl group and a phenyl group (on the phenyl ring a halogen atom, halogen substituted or unsubstituted C1 At least one group selected from the group consisting of 6 alkyl group and at least one group selected from the group consisting of halogen substituted or unsubstituted C1-6 alkoxy group) May be substituted));

(X) an indolinyl group (on the indoline ring, at least one halogen atom may be substituted);

(Y) an indolinyloxy group (a phenyl C1-6 alkyl group on an indoline ring [a halogen atom, a halogen substituted or unsubstituted C1 to 6 alkyl group and a halogen substituted or unsubstituted C1 to 6 alkyl group on a phenyl ring At least one group selected from the group consisting of alkoxy groups may be substituted] and at least one group selected from the group consisting of oxo groups may be substituted);

Spiro ring group represented by formula (H):

(Wherein, R ⁴¹ is
H1) hydrogen atom;
H2) C1-6 alkyl;
H3) a phenyl C1-6 alkyl group which may have a phenyl group as a substituent on the phenyl ring;
H4) phenyl group (on the phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group, a halogen-substituted or unsubstituted C1-6 alkoxy group, an amino group [on an amino group, a C1-6 alkyl group Group and a phenyl group (in which at least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group is substituted on the phenyl ring) At least one of the groups selected from the group consisting of (optionally substituted)], phenoxy group [on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group, and And at least one group selected from the group consisting of halogen-substituted or unsubstituted C1-6 alkoxy groups may be substituted] and [Piperidyl group [on the piperidine ring, at least one phenoxy group (on the phenyl ring, a group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group At least one kind of the group selected from the group consisting of the group consisting of] may optionally be substituted);
H5) Piperazinyl C1-6 alkyl group (in the piperazine ring, C1-6 alkoxycarbonyl group and phenyl C1-6 alkoxycarbonyl group [in the phenyl ring, a halogen atom, halogen substituted or unsubstituted C1-6 alkyl group And at least one group selected from the group consisting of a group selected from the group consisting of a halogen-substituted or unsubstituted C1-6 alkoxy group and a phenyl group may be substituted; May be);
H6) Piperazinylcarbonyl C1-6 alkyl group (C1-6 alkoxycarbonyl group on piperazine ring, halogen substituted or unsubstituted C1-6 alkyl group as a substituent on phenyl ring may be possessed Phenyl C1-6 alkoxycarbonyl group and phenyl C1-6 alkyl group [in the phenyl ring, at least one kind of group selected from the group consisting of halogen substituted or unsubstituted C1-6 alkyl group and phenyl group is substituted At least one of the groups selected from the group consisting of
H7) phenylcarbamoyl C1-6 alkyl group (wherein at least one halogen-substituted or unsubstituted C1-6 alkyl group may be substituted on the phenyl ring);
H8) benzoxazolyl C1-6 alkyl group (wherein at least one oxo group may be substituted on the benzoxazole ring);
H9) benzothiazolyl group;
H10) a tetrazolyl group (on the tetrazole ring, at least one phenyl group may be substituted);
H11) C1-6 alkylsulfonyl group;
H12) a phenylsulfonyl group (wherein at least one C1-6 alkyl group may be substituted on the phenyl ring);
H 13) phenylthiocarbamoyl group (wherein at least one halogen atom may be substituted on the phenyl ring);
H14) C1-8 alkoxycarbonyl group;
H15) phenyl C1-6 alkoxycarbonyl group (on the phenyl ring, a halogen atom, a C1-6 alkoxycarbonyl group, an amino group which may have a C1-6 alkoxycarbonyl group as a substituent, a halogen substituted or unsubstituted group At least one of a group selected from the group consisting of a C1-6 alkyl group, a halogen substituted or unsubstituted C1-6 alkoxy group, a nitro group and a C1-6 alkylthio group;
H 16) benzhydryloxycarbonyl group (wherein at least one halogen atom may be substituted on the phenyl ring);
H17) a phenyl substituted or unsubstituted phenyl C1-6 alkoxycarbonyl group;
H18) Naphthyl C1-6 alkoxycarbonyl group;
H19) pyridyl C1-6 alkoxycarbonyl group;
H20) C1-6 alkoxy substituted C1-6 alkoxycarbonyl group;
H21) Piperazinyl C1-6 alkoxycarbonyl group (C1-6 alkoxycarbonyl group and phenyl C1-6 alkoxycarbonyl group on piperazine ring [in phenyl ring, at least one halogen atom may be substituted At least one of the groups selected from the group consisting of
H22) Phenoxycarbonyl group (On the phenyl ring, at least one of groups selected from the group consisting of a C1-6 alkyl group and a C1-6 alkoxy group may be substituted);
H23) C1-6 alkanoyl;
H24) benzoyl group (wherein at least one halogen-substituted or unsubstituted C1-6 alkyl group may be substituted on the phenyl ring);
H25) phenyl C1-6 alkanoyl group (wherein at least one halogen-substituted or unsubstituted C1-6 alkyl group may be substituted on the phenyl ring);
H26) phenoxy C1-6 alkanoyl group (1 to 3 halogen atoms may be substituted on the phenyl ring);
H27) Piperazinyl C2-6 alkanoyl group (C1-6 alkanoyl group on piperazine ring, phenyl C1-6 alkyl group [phenyl group on halogen ring, halogen atom, halogen-substituted or unsubstituted C1-6 alkyl group Group and at least one group selected from the group consisting of halogen substituted or unsubstituted C1-6 alkoxy group may be substituted], phenyl C1-6 alkoxycarbonyl group [a halogen atom on a phenyl ring And at least one group selected from the group consisting of a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted], phenylcarbamoyl C1-6 An alkyl group [on the phenyl ring, a halogen atom, halogen-substituted or unsubstituted C.sub.1-6 alkyl, Group and at least one group selected from the group consisting of halogen substituted or unsubstituted C1-6 alkoxy group may be substituted], phenylcarbamoyl group [in the case of a halogen atom, halogen substitution or At least one selected from the group consisting of an unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group] and a group consisting of a benzoxazolyl group At least one selected group may be substituted);
H28) phenylcarbamoyl group (on the phenyl ring, a halogen atom, an amino group which may have a C1-6 alkyl group as a substituent, a carboxyl group, a C1-6 alkoxycarbonyl group, a halogen substituted or unsubstituted C1-6 1 to 3 groups selected from the group consisting of an alkyl group, a halogen-substituted or unsubstituted C1-6 alkoxy group, a piperazinyl group which may have a C1-6 alkyl group as a substituent on a piperazine ring, and a morpholino group May be substituted);
H29) phenyl C1-6 alkylcarbamoyl group (wherein at least one of the groups selected from the group consisting of halogen-substituted or unsubstituted C1-6 alkyl groups and halogen-substituted or unsubstituted C1-6 alkoxy groups on the phenyl ring Species may be substituted);
Or
H30) Piperazinylcarbonyl group (C1-6 alkoxycarbonyl group, phenyl C1-6 alkoxycarbonyl group on piperazine ring [having at least one halogen-substituted or unsubstituted C1-6 alkyl group on phenyl ring Selected from the group consisting of [optionally substituted] and phenyl C1-6 alkyl group [wherein at least one halogen-substituted or unsubstituted C1-6 alkyl group may be substituted on the phenyl ring] At least one of the groups may be substituted)
Indicates )

Also, R ¹ and-(CH ₂ ) _n R ² are bonded to each other together with adjacent carbon atoms.

(Wherein RRR represents a piperidyl group [in which at least one phenoxy group (on a phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted on a phenyl ring At least one of a group selected from the group consisting of a C1-6 alkoxy group may be substituted).
And may form a spiro ring represented by

However, when R ¹ represents a hydrogen atom and R ² represents a group represented by formula (A), R ³ must not be an isopropyl group. When R ¹ represents a hydrogen atom, R ² represents a group represented by general formula (E), and m represents 0, R ¹¹ should not be a hydrogen atom. Furthermore, when R ¹ represents a hydrogen atom and R ² represents a group represented by formula (F), R ¹⁹ may not represent a hydrogen atom and R ²⁰ may not represent a tert-butoxycarbonyl group. ]

2. The pharmaceutical composition according to the above 1, wherein the pharmaceutical composition is an antituberculosis drug.

3. An oxazole compound is
4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid 3- (4-trifluoromethylphenyl) -2-propenyl ester,
(S) -4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid 3- (4-trifluoromethylphenyl) -2-propenyl ester,
(R) -4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid 3- (4-trifluoromethylphenyl) -2-propenyl ester,
2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethoxyphenoxy) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole,
(S) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethoxyphenoxy) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b ] Oxazole,
(R) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethoxyphenoxy) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b ] Oxazole,
2-Methyl-6-nitro-2- {4- [1- (4-trifluoromethoxybenzyl) piperidin-4-yl] phenoxymethyl} -2,3-dihydro-imidazo [2,1-b] oxazole,
(S) -2-Methyl-6-nitro-2- {4- [1- (4-trifluoromethoxybenzyl) piperidin-4-yl] phenoxymethyl} -2,3-dihydro-imidazo [2,1-] b] oxazole,
(R) -2-Methyl-6-nitro-2- {4- [1- (4-trifluoromethoxybenzyl) piperidin-4-yl] phenoxymethyl} -2,3-dihydro-imidazo [2,1-] b] oxazole,
6-nitro-2- {4- [4- (4-trifluoromethoxyphenoxy) piperidin-1-yl] phenoxymethyl} -2,3-dihydro-imidazo [2,1-b] oxazole,
(S) -6-Nitro-2- {4- [4- (4-trifluoromethoxyphenoxy) piperidin-1-yl] phenoxymethyl} -2,3-dihydro-imidazo [2,1-b] oxazole,
(R) -6-Nitro-2- {4- [4- (4-trifluoromethoxyphenoxy) piperidin-1-yl] phenoxymethyl} -2,3-dihydro-imidazo [2,1-b] oxazole,
2-Methyl-6-nitro-2- {4- [3- (4-trifluoromethoxyphenoxy) -8-azabicyclo [3.2.1] octan-8-yl] phenoxymethyl} -2,3-dihydro Imidazo [2,1-b] oxazole,
(S) -2-Methyl-6-nitro-2- {4- [3- (4-trifluoromethoxyphenoxy) -8-azabicyclo [3.2.1] octan-8-yl] phenoxymethyl} -2 , 3-dihydroimidazo [2,1-b] oxazole,
(R) -2-Methyl-6-nitro-2- {4- [3- (4-trifluoromethoxyphenoxy) -8-azabicyclo [3.2.1] octan-8-yl] phenoxymethyl} -2 , 3-dihydroimidazo [2,1-b] oxazole,
(R) -2-Methyl-6-nitro-2- {4- [3- (4-trifluoromethoxyphenoxy) -8-azabicyclo [3.2.1] octan-8-yl] phenoxymethyl} -2 , 3-dihydroimidazo [2,1-b] oxazole 4-toluenesulfonate,
2-Methyl-6-nitro-2- [4- (4-trifluoromethylbenzylideneamino) piperazin-1-yl] -2,3-dihydroimidazo [2,1-b] oxazole,
(S) -2-Methyl-6-nitro-2- [4- (4-trifluoromethylbenzylideneamino) piperazin-1-yl] -2,3-dihydroimidazo [2,1-b] oxazole,
(R) -2-Methyl-6-nitro-2- [4- (4-trifluoromethylbenzylideneamino) piperazin-1-yl] -2,3-dihydroimidazo [2,1-b] oxazole,
2- [4- (5-chlorobenzofuran-2-ylmethyleneamino) piperazin-1-yl] -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole,
(S) -2- [4- (5-chlorobenzofuran-2-ylmethyleneamino) piperazin-1-yl] -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole ,
(R) -2- [4- (5-chlorobenzofuran-2-ylmethyleneamino) piperazin-1-yl] -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole ,
2- [4- (5-trifluoromethylbenzofuran-2-ylmethyleneamino) piperazin-1-yl] -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole;
(S) -2- [4- (5-Trifluoromethylbenzofuran-2-ylmethyleneamino) piperazin-1-yl] -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b ] Oxazole,
(R) -2- [4- (5-trifluoromethylbenzofuran-2-ylmethyleneamino) piperazin-1-yl] -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b ] Oxazole,
2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethylbenzyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole,
(S) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethylbenzyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b ] Oxazole,
(R) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethylbenzyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b ] Oxazole,
2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethoxybenzyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole,
(S) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethoxybenzyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b ] Oxazole,
(R) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethoxybenzyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b ] Oxazole,
2-Methyl-6-nitro-2- [4- (4-trifluoromethylphenoxy) piperidin-1-ylmethyl] -2,3-dihydroimidazo [2,1-b] oxazole,
(S) -2-Methyl-6-nitro-2- [4- (4-trifluoromethylphenoxy) piperidin-1-ylmethyl] -2,3-dihydroimidazo [2,1-b] oxazole,
(R) -2-Methyl-6-nitro-2- [4- (4-trifluoromethylphenoxy) piperidin-1-ylmethyl] -2,3-dihydroimidazo [2,1-b] oxazole,
2- [4- (4-trifluoromethoxyphenyl) piperazin-1-ylmethyl] -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole,
(S) -2- [4- (4-trifluoromethoxyphenyl) piperazin-1-ylmethyl] -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole;
(R) -2- [4- (4-trifluoromethoxyphenyl) piperazin-1-ylmethyl] -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole;
2- [4- (4-chlorophenyl) piperazin-1-ylmethyl] -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole,
(S) -2- [4- (4-chlorophenyl) piperazin-1-ylmethyl] -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole;
(R) -2- [4- (4-chlorophenyl) piperazin-1-ylmethyl] -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole;
2-Methyl-6-nitro-2- [4- (4'-trifluoromethylbiphenyl-4-ylmethyl) piperazin-1-ylmethyl] -2,3-dihydroimidazo [2,1-b] oxazole,
(S) -2-Methyl-6-nitro-2- [4- (4'-trifluoromethylbiphenyl-4-ylmethyl) piperazin-1-ylmethyl] -2,3-dihydroimidazo [2,1-b] Oxazole,
(R) -2-Methyl-6-nitro-2- [4- (4'-trifluoromethylbiphenyl-4-ylmethyl) piperazin-1-ylmethyl] -2,3-dihydroimidazo [2,1-b] Oxazole,
2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethylphenyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole,
(S) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethylphenyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b ] Oxazole,
(R) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethylphenyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b ] Oxazole,
2-Methyl-6-nitro-2- {4- [4- (4-chlorobenzyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole,
(S) -2-Methyl-6-nitro-2- {4- [4- (4-chlorobenzyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole ,
(R) -2-Methyl-6-nitro-2- {4- [4- (4-chlorobenzyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole ,
2-Methyl-6-nitro-2- {4- [4- (4-chlorophenyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole,
(S) -2-Methyl-6-nitro-2- {4- [4- (4-chlorophenyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole;
(R) -2-Methyl-6-nitro-2- {4- [4- (4-chlorophenyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole;
2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethoxybenzyloxycarbonyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole ,
(S) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethoxybenzyloxycarbonyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1 -B] oxazole,
(R) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethoxybenzyloxycarbonyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1 -B] oxazole,
2-Methyl-6-nitro-2- {4- [4- (3,4-dichlorobenzyloxycarbonyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole ,
(S) -2-Methyl-6-nitro-2- {4- [4- (3,4-dichlorobenzyloxycarbonyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1 -B] oxazole,
(R) -2-Methyl-6-nitro-2- {4- [4- (3,4-dichlorobenzyloxycarbonyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1 -B] oxazole,
2-Methyl-6-nitro-2- [4- (4-trifluoromethoxyphenoxy) piperidin-1-ylmethyl] -2,3-dihydroimidazo [2,1-b] oxazole,
(S) -2-Methyl-6-nitro-2- [4- (4-trifluoromethoxyphenoxy) piperidin-1-ylmethyl] -2,3-dihydroimidazo [2,1-b] oxazole,
(R) -2-Methyl-6-nitro-2- [4- (4-trifluoromethoxyphenoxy) piperidin-1-ylmethyl] -2,3-dihydroimidazo [2,1-b] oxazole,
2-Methyl-6-nitro-2- [4- (4-trifluoromethylphenyl) piperazin-1-ylmethyl] -2,3-dihydroimidazo [2,1-b] oxazole,
(S) -2-Methyl-6-nitro-2- [4- (4-trifluoromethylphenyl) piperazin-1-ylmethyl] -2,3-dihydroimidazo [2,1-b] oxazole,
(R) -2-Methyl-6-nitro-2- [4- (4-trifluoromethylphenyl) piperazin-1-ylmethyl] -2,3-dihydroimidazo [2,1-b] oxazole,
2-Methyl-6-nitro-2- [4- (5-trifluoromethoxybenzofuran-2-ylmethyleneamino) piperazin-1-ylmethyl] -2,3-dihydroimidazo [2,1-b] oxazole,
(S) -2-Methyl-6-nitro-2- [4- (5-trifluoromethoxybenzofuran-2-ylmethyleneamino) piperazin-1-ylmethyl] -2,3-dihydroimidazo [2,1-b ] Oxazole,
(R) -2-Methyl-6-nitro-2- [4- (5-trifluoromethoxybenzofuran-2-ylmethyleneamino) piperazin-1-ylmethyl] -2,3-dihydroimidazo [2,1-b ] Oxazole,
2-Methyl-6-nitro-2- [4- (5-trifluoromethylbenzofuran-2-ylmethyleneamino) piperazin-1-ylmethyl] -2,3-dihydroimidazo [2,1-b] oxazole,
(S) -2-Methyl-6-nitro-2- [4- (5-trifluoromethylbenzofuran-2-ylmethyleneamino) piperazin-1-ylmethyl] -2,3-dihydroimidazo [2,1-b ] Oxazole,
(R) -2-Methyl-6-nitro-2- [4- (5-trifluoromethylbenzofuran-2-ylmethyleneamino) piperazin-1-ylmethyl] -2,3-dihydroimidazo [2,1-b ] Oxazole,
2-Methyl-6-nitro-2- {4- [4- (4-chlorophenoxy) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole (S)- 2-Methyl-6-nitro-2- {4- [4- (4-chlorophenoxy) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole,
(R) -2-Methyl-6-nitro-2- {4- [4- (4-chlorophenoxy) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole ,
2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethylphenoxy) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole,
(S) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethylphenoxy) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b ] Oxazole,
(R) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethylphenoxy) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b ] Oxazole,
2-Methyl-6-nitro-2- {4- [1- (4-chlorobenzyl) piperidin-4-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole,
(S) -2-Methyl-6-nitro-2- {4- [1- (4-chlorobenzyl) piperidin-4-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole ,
(R) -2-Methyl-6-nitro-2- {4- [1- (4-chlorobenzyl) piperidin-4-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole ,
2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethylbenzyloxymethyl) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole ,
(R) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethylbenzyloxymethyl) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1 -B] oxazole,
(S) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethylbenzyloxymethyl) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1 -B] oxazole,
2-Methyl-6-nitro-2- {4- [4- (4-chlorophenoxymethyl) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole,
(R) -2-Methyl-6-nitro-2- {4- [4- (4-chlorophenoxymethyl) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] Oxazole,
(S) -2-Methyl-6-nitro-2- {4- [4- (4-chlorophenoxymethyl) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] Oxazole,
2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethylcinnamyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole,
(R) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethylcinnamyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-] b] oxazole,
(S) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethylcinnamyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-] b] oxazole,
2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethoxycinnamyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole,
(R) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethoxycinnamyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1- b] oxazole,
(S) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethoxycinnamyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-] b] oxazole,
2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethylphenoxymethyl) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole,
(R) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethylphenoxymethyl) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-] b] oxazole,
(S) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethylphenoxymethyl) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-] b] oxazole,
6-nitro-2- {4- [4- (4-trifluoromethoxybenzyloxy) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole,
(R) -6-nitro-2- {4- [4- (4-trifluoromethoxybenzyloxy) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole,
(S) -6-Nitro-2- {4- [4- (4-trifluoromethoxybenzyloxy) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole;
6-nitro-2- {4- [4- (4-trifluoromethoxyphenoxymethyl) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole,
(R) -6-Nitro-2- {4- [4- (4-trifluoromethoxyphenoxymethyl) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole,
(S) -6-Nitro-2- {4- [4- (4-trifluoromethoxyphenoxymethyl) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole;
6-nitro-2- {4- [4- (4-trifluoromethoxybenzyl) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole,
(R) -6-Nitro-2- {4- [4- (4-trifluoromethoxybenzyl) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole,
(S) -6-Nitro-2- {4- [4- (4-trifluoromethoxybenzyl) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole;
2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethoxybenzyl) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole,
(R) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethoxybenzyl) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b ] Oxazole,
(S) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethoxybenzyl) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b ] Oxazole,
2-Methyl-6-nitro-2- [4- {4- [4- (4-trifluoromethylphenyl) piperazin-1-yl] piperidin-1-yl} phenoxymethyl] -2,3-dihydroimidazo [ 2,1-b] oxazole,
(R) -2-Methyl-6-nitro-2- [4- {4- [4- (4-trifluoromethylphenyl) piperazin-1-yl] piperidin-1-yl} phenoxymethyl] -2,3 Dihydroimidazo [2,1-b] oxazole,
(S) -2-Methyl-6-nitro-2- [4- {4- [4- (4-trifluoromethylphenyl) piperazin-1-yl] piperidin-1-yl} phenoxymethyl] -2,3 Dihydroimidazo [2,1-b] oxazole,
2-Methyl-6-nitro-2- [4- {4- [4- (4-trifluoromethoxyphenoxy) benzyl] piperazin-1-yl} phenoxymethyl] -2,3-dihydroimidazo [2,1- b] oxazole,
(R) -2-Methyl-6-nitro-2- [4- {4- [4- (4-trifluoromethoxyphenoxy) benzyl] piperazin-1-yl} phenoxymethyl] -2,3-dihydroimidazo [ 2,1-b] oxazole,
(S) -2-Methyl-6-nitro-2- [4- {4- [4- (4-trifluoromethoxyphenoxy) benzyl] piperazin-1-yl} phenoxymethyl] -2,3-dihydroimidazo [ 2,1-b] oxazole,
6-nitro-2- [4- {4- [3- (4-trifluoromethoxyphenyl) propyl] piperidin-1-yl} phenoxymethyl] -2,3-dihydroimidazo [2,1-b] oxazole,
(R) -6-nitro-2- [4- {4- [3- (4-trifluoromethoxyphenyl) propyl] piperidin-1-yl} phenoxymethyl] -2,3-dihydroimidazo [2,1- b] oxazole,
(S) -6-Nitro-2- [4- {4- [3- (4-trifluoromethoxyphenyl) propyl] piperidin-1-yl} phenoxymethyl] -2,3-dihydroimidazo [2,1- b] oxazole,
2-Methyl-6-nitro-2- {4- [2- (4-trifluoromethoxyphenyl) oxazol-4-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole,
(R) -2-Methyl-6-nitro-2- {4- [2- (4-trifluoromethoxyphenyl) oxazol-4-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b ] Oxazole,
(S) -2-Methyl-6-nitro-2- {4- [2- (4-trifluoromethoxyphenyl) oxazol-4-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b ] Oxazole,
6-nitro-2- {4- [4- (4-chlorophenoxymethyl) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole,
(R) -6-Nitro-2- {4- [4- (4-chlorophenoxymethyl) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole;
(S) -6-Nitro-2- {4- [4- (4-chlorophenoxymethyl) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole;
2-Methyl-6-nitro-2- {4- [4- (5-trifluoromethylbenzofuran-2-ylmethyl) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b ] Oxazole,
(R) -2-Methyl-6-nitro-2- {4- [4- (5-trifluoromethylbenzofuran-2-ylmethyl) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2 , 1-b] oxazole,
(S) -2-Methyl-6-nitro-2- {4- [4- (5-trifluoromethylbenzofuran-2-ylmethyl) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2 , 1-b] oxazole,
2-Methyl-6-nitro-2- {4- [2- (4-chlorophenyl) oxazol-4-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole,
(R) -2-Methyl-6-nitro-2- {4- [2- (4-chlorophenyl) oxazol-4-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole,
(S) -2-Methyl-6-nitro-2- {4- [2- (4-chlorophenyl) oxazol-4-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole,
6-nitro-2- {4- [4- (4-trifluoromethylphenoxymethyl) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole,
(R) -6-Nitro-2- {4- [4- (4-trifluoromethylphenoxymethyl) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole;
(S) -6-Nitro-2- {4- [4- (4-trifluoromethylphenoxymethyl) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole,
2-Methyl-6-nitro-2- {4- [4- (4-bromocinnamyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole,
(R) -2-Methyl-6-nitro-2- {4- [4- (4-bromocinnamyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole;
(S) -2-Methyl-6-nitro-2- {4- [4- (4-bromocinnamyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole;
2-Methyl-6-nitro-2- [2- (4-trifluoromethoxyphenyl) -1,2,3-tetrahydroisoquinolin-6-yloxymethyl] -2,3-dihydroimidazo [2,1 -B] oxazole,
(R) -2-Methyl-6-nitro-2- [2- (4-trifluoromethoxyphenyl) -1,2,3-tetrahydroisoquinolin-6-yloxymethyl] -2,3-dihydroimidazo [2,1-b] oxazole, and (S) -2-methyl-6-nitro-2- [2- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydroisoquinolin-6-yl The pharmaceutical composition according to the above 1 or 2, which is at least one selected from the group consisting of oxymethyl] -2,3-dihydroimidazo [2,1-b] oxazole.
In the present specification, each group represented by R ¹ and (A) to (G) is specifically as follows.

  As a halogen atom, a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom are shown, for example.

  The C1-6 alkyl group is a linear or branched alkyl group having 1 to 6 carbon atoms, and examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group and an n- group. A butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, an n-pentyl group, a neopentyl group, an n-hexyl group, an isohexyl group, a 3-methylpentyl group and the like can be mentioned.

  The C1-6 alkoxy group is a group composed of a C1-6 alkyl group as defined above and an oxygen atom, and for example, a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group And isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, n-hexyloxy, isohexyloxy, 3-methylpentoxy and the like.

  A C1-6 alkoxy-C1-6 alkyl group is a group comprised by said C1-6 alkyl group and C1-6 alkoxy group, Comprising: For example, methoxymethyl group, 2-methoxyethyl group, 3-methoxypropyl Group, 4-methoxybutyl group, 5-methoxypentyl group, 6-methoxyhexyl group, ethoxymethyl group, 2-ethoxyethyl group, 3-ethoxypropyl group, 2-isopropoxyethyl group, tert-butoxymethyl group, 2 -(Tert- butoxy) ethyl group, 3- (tert- butoxy) propyl group, 6- (tert- butoxy) hexyl group, 4- (tert- butoxy) butyl group etc. can be mentioned.

  The halogen-substituted or unsubstituted C1-6 alkyl group is a linear or branched alkyl group having 1 to 6 carbon atoms as defined above, and the above-mentioned alkyl in which 1 to 7 halogen atoms are substituted. Group, for example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, n-pentyl group, neopentyl group, n-hexyl group Group, isohexyl group, 3-methylpentyl group, fluoromethyl group, difluoromethyl group, trifluoromethyl group, chloromethyl group, dichloromethyl group, trichloromethyl group, bromomethyl group, dibromomethyl group, dichlorofluoromethyl group, 2,2-trifluoroethyl group, pentafluoroethyl group, 2-chloroethyl group, 3,3,3-t Fluoropropyl group, heptafluoropropyl group, heptafluoroisopropyl group, 3-chloropropyl group, 2-chloropropyl group, 3-bromopropyl group, 4,4,4-trifluorobutyl group, 4,4,4,3 trifluorobutyl group , 3-pentafluorobutyl group, 4-chlorobutyl group, 4-bromobutyl group, 2-chlorobutyl group, 5,5,5-trifluoropentyl group, 5-chloropentyl group, 6,6,6-trifluorohexyl group Group, 6-chlorohexyl group etc. can be mentioned.

  The halogen-substituted or unsubstituted C1-6 alkoxy group is a C1-6 alkoxy group as defined above and the above alkoxy group substituted by 1 to 7 halogen atoms, and examples thereof include a methoxy group, an ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, tert-butoxy group, sec-butoxy group, n-pentoxy group, neopentoxy group, n-hexyloxy group, isohexyloxy group, 3-methyl pen Toxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chloromethoxy, dichloromethoxy, trichloromethoxy, bromomethoxy, dibromomethoxy, dichlorofluoromethoxy, 2,2,2-trifluoroethoxy Group, pentafluoroethoxy group, 2-chloroet Group, 3,3,3-trifluoropropoxy group, heptafluoropropoxy group, heptafluoroisopropoxy group, 3-chloropropoxy group, 2-chloropropoxy group, 3-bromopropoxy group, 4,4,4-trithio Fluorobutoxy group, 4,4,4,3,3-pentafluorobutoxy group, 4-chlorobutoxy group, 4-bromobutoxy group, 2-chlorobutoxy group, 5,5,5-trifluoropentoxy group, 5 -Chloropentoxy group, 6,6, 6- trifluorohexyloxy group, 6-chlorohexyloxy group etc. can be mentioned.

  A phenyl C1-6 alkyl group (on the phenyl ring, a phenyl C1-6 alkoxy group; a halogen substituted or unsubstituted C1-6 alkyl group; a halogen substituted or unsubstituted C1-6 alkoxy group and a phenoxy group [on the phenyl ring In which at least one member selected from the group consisting of halogen-substituted or unsubstituted C.sub.1-6 alkoxy group may be substituted) may be substituted, for example, Benzyl group, 1-phenethyl group, 2-phenethyl group, 3-phenylpropyl group, 2-phenylpropyl group, 4-phenylbutyl group, 5-phenylpentyl group, 4-phenylpentyl group, 6-phenylhexyl group, 2 -Benzyloxybenzyl group, 3-benzyloxybenzyl group, 4-benzyloxybenzyl group, 2,4-diben Roxybenzyl group, 2,4,6-tribenzyloxybenzyl group, 2- (2-phenethyloxy) benzyl group, 3- (2-phenethyloxy) benzyl group, 4- (2-phenethyloxy) benzyl group, 2- (3-phenylpropoxy) benzyl group, 3- (3-phenylpropoxy) benzyl group, 4- (3-phenylpropoxy) benzyl group, 2- (4-phenylbutoxy) benzyl group, 3- (4-phenyl group) Butoxy) benzyl group, 4- (4-phenylbutoxy) benzyl group, 2- (5-phenylpentyloxy) benzyl group, 3- (5-phenylpentyloxy) benzyl group, 4- (5-phenylpentyloxy) benzyl Group, 2- (6-phenylhexyloxy) benzyl group, 3- (6-phenylhexyloxy) benzyl group, 4- (4- -Phenylhexyloxy) benzyl group, 2-methylbenzyl group, 2,3-dimethylbenzyl group, 3,4-dimethylbenzyl group, 3,5-dimethylbenzyl group, 2,6-dimethylbenzyl group, 2,4- Dimethylbenzyl group, 2,5-dimethylbenzyl group, 2,4,6-trimethylbenzyl group, 3,5-ditrifluoromethylbenzyl group, 2,4,6-trifluoromethylbenzyl group, 2-trifluoromethylbenzyl group Group, 3-trifluoromethylbenzyl group, 4-trifluoromethylbenzyl group, 2-trifluoromethoxybenzyl group, 3-trifluoromethoxybenzyl group, 4-trifluoromethoxybenzyl group, 3-methoxybenzyl group, 2, 3-dimethoxybenzyl group, 3,4-dimethoxybenzyl group, 3,5-dimethoxybenzyl group 2,6-dimethoxybenzyl group, 2,4-dimethoxybenzyl group, 2,5-dimethoxybenzyl group, 2,4,6-trimethoxybenzyl group, 2,6-ditrifluoromethoxybenzyl group 2,3, 4-trifluoromethoxybenzyl group, 1- (4-benzyloxyphenyl) ethyl group, 1- (3-benzyloxyphenyl) ethyl group, 1- (2-benzyloxyphenyl) ethyl group, 1- (2-trioxy) Fluoromethylphenyl) ethyl group, 1- (3-trifluoromethylphenyl) ethyl group, 1- (4-trifluoromethylphenyl) ethyl group, 1- (2-trifluoromethoxyphenyl) ethyl group, 1- (3) -Trifluoromethoxyphenyl) ethyl group, 1- (4-trifluoromethoxyphenyl) ethyl group, 2- (4-benzyloxy) group -Yl) ethyl group, 2- (3-benzyloxyphenyl) ethyl group, 2- (2-benzyloxyphenyl) ethyl group, 2- (2-trifluoromethylphenyl) ethyl group, 2- (3-trifluoromethyl) Phenyl) ethyl group, 2- (4-trifluoromethylphenyl) ethyl group, 2- (2-trifluoromethoxyphenyl) ethyl group, 2- (3-trifluoromethoxyphenyl) ethyl group, 2- (4-trimethyl) Fluoromethoxyphenyl) ethyl group, 3- (4-benzyloxyphenyl) propyl group, 3- (3-benzyloxyphenyl) propyl group, 3- (2-benzyloxyphenyl) propyl group, 3- (2-trifluoro) Methylphenyl) propyl group, 3- (3-trifluoromethylphenyl) propyl group, 3- (4-trifluoromethyl) Phenyl) propyl group, 3- (2-trifluoromethylphenyl) propyl group, 3- (3-trifluoromethoxyphenyl) propyl group, 3- (4-trifluoromethoxyphenyl) propyl group, 4- (3-triol) Fluoromethylphenyl) butyl group, 5- (4-trifluoromethylphenyl) pentyl group, 4- (4-trifluoromethylphenyl) pentyl group, 4- (4-trifluoromethoxyphenyl) pentyl group, 6- (3) -Trifluoromethylphenyl) hexyl group, 6- (4-trifluoromethylphenyl) hexyl group, 6- (4-trifluoromethoxyphenyl) hexyl group, 2-phenoxybenzyl group, 3-phenoxybenzyl group, 4-phenoxy Benzyl, 2,5-diphenoxybenzyl, 2,4,6-triphenoxyben Zyl group, 1- (4-phenoxyphenyl) ethyl group, 1- (3-phenoxyphenyl) ethyl group, 1- (2-phenoxyphenyl) ethyl group, 3- (4-phenoxyphenyl) propyl group, 3- ( 3-phenoxyphenyl) propyl group, 3- (2-phenoxyphenyl) propyl group, 2- (4-trifluoromethoxyphenoxy) benzyl group, 3- (4-trifluoromethoxyphenoxy) benzyl group, 4- (4-) Trifluoromethoxyphenoxy) benzyl group, 1- (4- (4-trifluoromethoxyphenoxy) phenyl) ethyl group, 1- (3- (4-trifluoromethoxyphenoxy) phenyl) ethyl group, 1- (2- (2- (2- (4- (4-trifluoromethoxyphenoxy) phenyl) ethyl group) 4-trifluoromethoxyphenoxy) phenyl) ethyl group, 3- (4- (4-trifluoromethoxyphenoxy) Phenyl) propyl group, 3- (3- (4-trifluoromethoxyphenoxy) phenyl) propyl group, 3- (2- (4-trifluoromethoxyphenoxy) phenyl) propyl group, 2-trifluoromethyl-3-trile A phenyl C1-6 alkyl group such as fluoromethoxybenzyl group, 2-benzyloxy-3-trifluoromethoxybenzyl group, 3-phenoxy-4-trifluoromethylbenzyl group (on the phenyl ring, a phenyl C1-6 alkoxy group A halogen-substituted or unsubstituted C1-6 alkyl group, a halogen-substituted or unsubstituted C1-6 alkoxy group and a phenoxy group [in the phenyl ring, 1 to 3 halogen-substituted or unsubstituted C1-6 alkoxy groups] Even if 1 to 3 groups selected from the group consisting of [optionally substituted] are substituted Stomach) can be mentioned.

  Examples of the biphenylyl C1-6 alkyl group include a 2-biphenylylmethyl group, 2- (2-biphenylyl) ethyl group, 3- (2-biphenylyl) propyl group, 4- (2-biphenylyl) butyl group, 5- (2-biphenylyl) pentyl group, 6- (2-biphenylyl) hexyl group, 3-biphenylylmethyl group, 2- (3-biphenylyl) ethyl group, 3- (3-biphenylyl) propyl group, 4- (3-biphenylyl) group Biphenylyl) butyl group, 5- (3-biphenylyl) pentyl group, 6- (3-biphenylyl) hexyl group, 4-biphenylylmethyl group, 2- (4-biphenylyl) ethyl group, 3- (4-biphenylyl) propyl Group such as phenyl, 4- (4-biphenylyl) butyl, 5- (4-biphenylyl) pentyl, 6- (4-biphenylyl) hexyl and the like To 6 alkyl groups (on the phenyl ring, a phenyl C1-6 alkoxy group, a halogen-substituted or unsubstituted C1-6 alkyl group, a halogen-substituted or unsubstituted C1-6 alkoxy group, and a halogen as a substituent on the phenyl ring One to three groups selected from the group consisting of phenoxy groups which may have at least one substituted or unsubstituted C1-6 alkoxy group may be substituted, and the like.

  The phenyl C2-6 alkenyl group means a group composed of a phenyl group and an alkenyl group having 2 to 6 carbon atoms and 1 to 3 double bonds, and the phenyl C2-6 alkenyl group is a trans isomer and a cis group. Includes both of the body. As such a phenyl C2-6 alkenyl group, for example, 3-phenyl-2-propenyl group (conventional name: cinnamyl group), 4-phenyl-2-butenyl group, 4-phenyl-3-butenyl group, 5- Phenyl-4-pentenyl group, 5-phenyl-3-pentenyl group, 6-phenyl-5-hexenyl group, 6-phenyl) -4-hexenyl group, 6-phenyl-3-hexenyl group, 4-phenyl-1, 4, Examples include 3-butadienyl group, 6-phenyl-1,3,5-hexatrienyl group and the like.

  The C1-6 alkylsulfonyl group is a group composed of an alkyl group having 1 to 6 carbon atoms and a sulfonyl group, and for example, a methanesulfonyl group, an ethanesulfonyl group, a propanesulfonyl group, a butanesulfonyl group And pentanesulfonyl group, hexanesulfonyl group and the like.

  The benzenesulfonyl group which may be substituted by a C1-6 alkyl group is, for example, benzenesulfonyl group, o-toluenesulfonyl group, m-toluenesulfonyl group, p-toluenesulfonyl group, 2-ethylbenzenesulfonyl group, 3- Ethylbenzenesulfonyl group, 4-ethylbenzenesulfonyl group, 2-propylbenzenesulfonyl group, 3-propylbenzenesulfonyl group, 4-propylbenzenesulfonyl group, 2,3-dimethylbenzenesulfonyl group, 2,4-dimethylbenzenesulfonyl group, 2 Mention may be made of a benzenesulfonyl group in which 1 to 3 C1-6 alkyl groups such as 4, 6, 4-trimethylbenzenesulfonyl group may be substituted.

  The C1-6 alkanoyl group is a group derived from an aliphatic carboxylic acid having 1 to 6 carbon atoms, and examples thereof include a formyl group, an acetyl group, a propionyl group, a butyryl group, a pentanoyl group, and a hexanoyl group. Etc.

  The C1-6 alkoxycarbonyl group is a group composed of a C1-6 alkoxy group as defined above and a carbonyl group, and for example, a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, an isopropoxycarbonyl group, n-butoxycarbonyl group, isobutoxycarbonyl group, tert-butoxycarbonyl group, sec-butoxycarbonyl group, n-pentoxycarbonyl group, neopentoxy carbonyl group, n-hexyloxycarbonyl group, isohexyloxycarbonyl group, 3 -A methyl pentoxy carbonyl group etc. can be mentioned.

  Phenyl C1-6 alkoxycarbonyl group [on the phenyl ring, selected from the group consisting of a phenyl C1-6 alkoxy group, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group At least one of the above-mentioned groups may be substituted] means a phenyl C.sub.1-6 alkoxy group, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted group on the phenyl ring defined above A group selected from the group consisting of a C1-6 alkoxy group is a group consisting of a phenyl C1-6 alkoxy group optionally substituted with 1 to 3 substituted groups and a carbonyl group, and examples thereof include a benzyloxycarbonyl group, 1 -Phenylethoxycarbonyl group, 2-phenylethoxycarbonyl group, 3-phenylpropoxycarbonyl group, -Phenylpropoxycarbonyl group, 4-phenylbutoxycarbonyl group, 5-phenylpentoxy carbonyl group, 4-phenylpentoxy carbonyl group, 6-phenylhexyloxycarbonyl group, 2-benzyloxybenzyloxycarbonyl group, 3-benzyloxy Benzyloxycarbonyl group, 4-benzyloxybenzyloxycarbonyl group, 2,4-dibenzyloxybenzyloxycarbonyl group, 3,4,5-benzyloxybenzyloxycarbonyl group, 2-trifluoromethylbenzyloxycarbonyl group, 2 -Methylbenzyloxycarbonyl group, 3-methylbenzyloxycarbonyl group, 4-methylbenzyloxycarbonyl group, 2,6-dimethylbenzyloxycarbonyl group, 2,4,6-trimethylbenzylo group A carbonyl group, a 2,3-ditrifluoromethylbenzyloxycarbonyl group, a 2,4,6-tri (trifluoromethyl) benzyloxycarbonyl group, a 2-methoxybenzyloxycarbonyl group, a 3-methoxybenzyloxycarbonyl group, 4 -Methoxybenzyloxycarbonyl group, 2,4-dimethoxybenzyloxycarbonyl group, 3,4,5-trimethoxybenzyloxycarbonyl group, 2,5-ditrifluoromethoxybenzyloxycarbonyl group, 2,4,6-tri ( (Trifluoromethoxy) benzyloxycarbonyl group, 3-trifluoromethylbenzyloxycarbonyl group, 4-trifluoromethylbenzyloxycarbonyl group, 2-trifluoromethoxybenzyloxycarbonyl group, 3-trifluoromethoxybenzyl Oxycarbonyl group, 4-trifluoromethoxybenzyloxycarbonyl group, 2- (2-trifluoromethylphenyl) ethoxycarbonyl group, 2- (3-trifluoromethylphenyl) ethoxycarbonyl group, 2- (4-trifluoromethyl) Phenyl) ethoxycarbonyl group, 2- (2-trifluoromethoxyphenyl) ethoxycarbonyl group, 2- (3-trifluoromethoxyphenyl) ethoxycarbonyl group, 2- (4-trifluoromethoxyphenyl) ethoxycarbonyl group, 3- (4-benzyloxyphenyl) propoxycarbonyl group, 3- (3-benzyloxyphenyl) propoxycarbonyl group, 3- (2-benzyloxyphenyl) propoxycarbonyl group, 3- (2-trifluoromethylphenyl) propoxycarbo group Group, 3- (3-trifluoromethylphenyl) propoxycarbonyl group, 3- (4-trifluoromethylphenyl) propoxycarbonyl group, 3- (2-trifluoromethoxyphenyl) propoxycarbonyl group, 3- (3- Trifluoromethoxyphenyl) propoxycarbonyl group, 3- (4-trifluoromethoxyphenyl) propoxycarbonyl group, 4- (3-benzyloxyphenyl) butoxycarbonyl group, 4- (4-benzyloxyphenyl) butoxycarbonyl group, 4 -(3-trifluoromethylphenyl) butoxycarbonyl group, 4- (4-trifluoromethylphenyl) butoxycarbonyl group, 5- (3-benzyloxyphenyl) pentoxycarbonyl group, 5- (4-benzyloxyphenyl) group Pentox carboni Group, 5- (4-trifluoromethylphenyl) pentoxy carbonyl group, 4- (4-trifluoromethylphenyl) pentoxy carbonyl group, 4- (4-trifluoromethoxyphenyl) pentoxy carbonyl group, 6- ( 3-benzyloxyphenyl) hexyloxycarbonyl group, 6- (4-benzyloxyphenyl) hexyloxycarbonyl group, 6- [3- (2-phenethyloxy) phenyl] hexyloxycarbonyl group, 6- [4- (2) -Phenethyloxy) phenyl] hexyloxycarbonyl group, 6- [3- (3-phenylpropoxy) phenyl] hexyloxycarbonyl group, 6- [4- (4-phenylbutoxy) phenyl] hexyloxycarbonyl group, 6- [4- (5-phenylpentyloxy) phenyl] hexyl Oxycarbonyl group, 6- [4- (6-phenylhexyloxy) phenyl] hexyloxycarbonyl group, 6- (3-trifluoromethylphenyl) hexyloxycarbonyl group, 6- (4-trifluoromethylphenyl) hexyloxy Carbonyl group, 6- (4-trifluoromethoxyphenyl) hexyloxycarbonyl group, 2-trifluoromethyl-4-benzyloxybenzyloxycarbonyl group, 3-trifluoromethoxy-5-benzyloxybenzyloxycarbonyl group, 2- Trifluoromethyl-3-trifluoromethoxybenzyloxycarbonyl group etc. can be mentioned.

  Phenyl C1-6 alkyl group [on the phenyl ring is selected from the group consisting of phenyl C1-6 alkoxy group, halogen substituted or unsubstituted C1-6 alkyl group and halogen substituted or unsubstituted C1-6 alkoxy group As at least one kind of the group may be substituted], for example, benzyl group, 1-phenethyl group, 2-phenethyl group, 3-phenylpropyl group, 2-phenylpropyl group, 4-phenylbutyl group, 5 -Phenylpentyl group, 4-phenylpentyl group, 6-phenylhexyl group, 2-benzyloxybenzyl group, 3-benzyloxybenzyl group, 4-benzyloxybenzyl group, 2,4-dibenzyloxybenzyl group, 2, 4,6-tribenzyloxybenzyl group, 2- (2-phenethyloxy) benzyl group, 3- (2-fe 2-hydroxy-3-benzyl, 4- (2-phenethyloxy) benzyl, 2- (3-phenylpropoxy) benzyl, 3- (3-phenylpropoxy) benzyl, 4- (3-phenylpropoxy) benzyl, 2 -(4-phenylbutoxy) benzyl group, 3- (4-phenylbutoxy) benzyl group, 4- (4-phenylbutoxy) benzyl group, 2- (5-phenylpentyloxy) benzyl group, 3- (5-phenyl group) Pentyloxy) benzyl group, 4- (5-phenylpentyloxy) benzyl group, 2- (6-phenylhexyloxy) benzyl group, 3- (6-phenylhexyloxy) benzyl group, 4- (6-phenylhexyloxy ) Benzyl group, 2-methylbenzyl group, 2,3-dimethylbenzyl group, 3,4-dimethylbenzyl group, 3,5-dimethylbenzyl group, 2,6-dimethylbenzyl group, 2,4-dimethylbenzyl group, 2,5-dimethylbenzyl group, 2,4,6-trimethylbenzyl group, 3,5-ditrifluoromethylbenzyl group 2,4,6-Trifluoromethylbenzyl group, 2-trifluoromethylbenzyl group, 3-trifluoromethylbenzyl group, 4-trifluoromethylbenzyl group, 2-trifluoromethoxybenzyl group, 3-trifluoromethoxy Benzyl group, 4-trifluoromethoxybenzyl group, 3-methoxybenzyl group, 2,3-dimethoxybenzyl group, 3,4-dimethoxybenzyl group, 3,5-dimethoxybenzyl group, 2,6-dimethoxybenzyl group, 2 , 4-Dimethoxybenzyl group, 2,5-dimethoxybenzyl group, 2,4,6-trimethoxy group Nidyl group, 2,6-ditrifluoromethoxybenzyl group, 2,3,4-trifluoromethoxybenzyl group, 1- (4-benzyloxyphenyl) ethyl group, 1- (3-benzyloxyphenyl) ethyl group, 1 -(2-benzyloxyphenyl) ethyl group, 1- (2-trifluoromethylphenyl) ethyl group, 1- (3-trifluoromethylphenyl) ethyl group, 1- (4-trifluoromethylphenyl) ethyl group, 1- (2-trifluoromethoxyphenyl) ethyl group, 1- (3-trifluoromethoxyphenyl) ethyl group, 1- (4-trifluoromethoxyphenyl) ethyl group, 2- (4-benzyloxyphenyl) ethyl group , 2- (3-benzyloxyphenyl) ethyl group, 2- (2-benzyloxyphenyl) ethyl group, 2- (2-t) Fluoromethylphenyl) ethyl group, 2- (3-trifluoromethylphenyl) ethyl group, 2- (4-trifluoromethylphenyl) ethyl group, 2- (2-trifluoromethoxyphenyl) ethyl group, 2- (3 -Trifluoromethoxyphenyl) ethyl group, 2- (4-trifluoromethoxyphenyl) ethyl group, 3- (4-benzyloxyphenyl) propyl group, 3- (3-benzyloxyphenyl) propyl group, 3- (2 -Benzyloxyphenyl) propyl group, 3- (2-trifluoromethylphenyl) propyl group, 3- (3-trifluoromethylphenyl) propyl group, 3- (4-trifluoromethylphenyl) propyl group, 3- (3- (4-trifluoromethylphenyl) propyl group) 2-trifluoromethoxyphenyl) propyl group, 3- (3-trifluoromethoxyphenyl) group Pill, 3- (4-trifluoromethoxyphenyl) propyl, 4- (3-trifluoromethylphenyl) butyl, 5- (4-trifluoromethylphenyl) pentyl, 4- (4-trifluoromethyl) Phenyl) pentyl group, 4- (4-trifluoromethoxyphenyl) pentyl group, 6- (3-trifluoromethylphenyl) hexyl group, 6- (4- trifluoromethylphenyl) hexyl group, 6- (4- tri- Fluorine methoxyphenyl) such as fluoromethoxyphenyl) hexyl group, 2-trifluoromethyl-3-trifluoromethoxybenzyl group, 2-benzyloxy-3-trifluoromethoxybenzyl group, 3-phenoxy-4-trifluoromethylbenzyl group, etc. 6 alkyl group (on the phenyl ring, a phenyl C.sub.1-6 alkoxy group, a halogen And the group selected from the group consisting of a substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted with 1 to 3 groups).

  Examples of the biphenylyl C1-6 alkoxycarbonyl group include 2-biphenylyl methoxycarbonyl group, 2- (2-biphenylyl) ethoxycarbonyl group, 3- (2-biphenylyl) propoxycarbonyl group, 4- (2-biphenylyl) butoxy Carbonyl group, 5- (2-biphenylyl) pentoxy carbonyl group, 6- (2-biphenylyl) hexyloxycarbonyl group, 3-biphenylylmethoxycarbonyl group, 2- (3-biphenylyl) ethoxycarbonyl group, 3- (3) -Biphenylyl) propoxycarbonyl group, 4- (3-biphenylyl) butoxycarbonyl group, 5- (3-biphenylyl) pentoxy carbonyl group, 6- (3-biphenylyl) hexyloxycarbonyl group, 4-biphenylyl methoxycarbonyl group, 2- (4-bit) Phenylyl) ethoxycarbonyl group, 3- (4-biphenylyl) propoxycarbonyl group, 4- (4-biphenylyl) butoxycarbonyl group, 5- (4-biphenylyl) pentoxy carbonyl group, 6- (4-biphenylyl) hexyloxycarbonyl And the like.

  Examples of the benzoxazolyl C1-6 alkyl group (wherein at least one oxo group may be substituted on the benzoxazole ring) include, for example, benzoxazol-2-ylmethyl group and benzoxazol-4-ylmethyl group. Group, benzoxazol-5-ylmethyl group, benzoxazol-6-ylmethyl group, benzoxazol-7-ylmethyl group, 2- (benzoxazol-4-yl) ethyl group, 1- (benzoxazol-5-yl) ethyl Group, 3- (benzoxazol-6-yl) propyl group, 4- (benzoxazol-7-yl) butyl group, 5- (benzoxazol-2-yl) pentyl group, 6- (benzoxazol-4-yl) group ) Hexyl group, 2-methyl-3- (benzoxazol-5-yl) propyl group, 1, -Dimethyl-2- (benzoxazol-2-yl) ethyl group, (2,3-dihydro-2-oxo-benzoxazol-3-yl) methyl group, (2,3-dihydro-2-oxo-benzoxazole) -4-yl) methyl group, (2,3-dihydro-2-oxo-benzoxazol-5-yl) methyl group, (2,3-dihydro-2-oxo-benzoxazol-6-yl) methyl group, (2,3-dihydro-2-oxo-benzoxazol-7-yl) methyl group, 2- (benzoxazol-6-yl) ethyl group, 2- (benzoxazol-7-yl) ethyl group, 2- ( 2,3-Dihydro-2-oxo-benzoxazol-3-yl) ethyl group, 2- (2,3-dihydro-2-oxo-benzoxazol-4-yl) ethyl group, 2 (2,3-dihydro-2-oxo-benzoxazol-5-yl) ethyl group, 2- (2,3-dihydro-2-oxo-benzoxazol-6-yl) ethyl group, 2- (2,3 -Dihydro-2-oxo-benzoxazol-7-yl) ethyl group, 3- (benzoxazol-2-yl) propyl group, 3- (benzoxazol-4-yl) propyl group, 3- (benzoxazole-5) -Yl) propyl group, 3- (benzoxazol-7-yl) propyl group, 3- (2,3-dihydro-2-oxo-benzoxazol-3-yl) propyl group, 3- (2,3-dihydro) group -2-oxo-benzoxazol-4-yl) propyl group, 3- (2,3-dihydro-2-oxo-benzoxazol-5-yl) propyl group, 3- (2,3-di) Hydro-2-oxo-benzoxazol-6-yl) propyl group, 3- (2,3-dihydro-2-oxo-benzoxazol-7-yl) propyl group, 4- (benzoxazol-2-yl) butyl Group, 4- (benzoxazol-4-yl) butyl group, 4- (benzoxazol-5-yl) butyl group, 4- (benzoxazol-6-yl) butyl group, 4- (2,3-dihydro-) 2-oxo-benzoxazol-3-yl) butyl group, 4- (2,3-dihydro-2-oxo-benzoxazol-4-yl) butyl group, 4- (2,3-dihydro-2-oxo-) Benzoxazol-5-yl) butyl group, 4- (2,3-dihydro-2-oxo-benzoxazol-6-yl) butyl group, 4- (2,3-dihydro-2-oxo-be) Zooxazol-7-yl) butyl group, 5- (benzoxazol-4-yl) pentyl group, 5- (benzoxazol-5-yl) pentyl group, 5- (benzoxazol-6-yl) pentyl group, 5 -(Benzoxazol-7-yl) pentyl group, 5- (2,3-dihydro-2-oxo-benzoxazol-3-yl) pentyl group, 5- (2,3-dihydro-2-oxo-benzoxazole) -4-yl) pentyl group, 5- (2,3-dihydro-2-oxo-benzoxazol-5-yl) pentyl group, 5- (2,3-dihydro-2-oxo-benzoxazol-6-yl) ) Pentyl group, 5- (2,3-dihydro-2-oxo-benzoxazol-7-yl) pentyl group, 6- (benzoxazol-2-yl) hexyl group 6- (benzoxazol-5-yl) hexyl group, 6- (benzoxazol-6-yl) hexyl group, 6- (benzoxazol-7-yl) hexyl group, 6- (2,3-dihydro-2-) Oxo-benzoxazol-3-yl) hexyl group, 6- (2,3-dihydro-2-oxo-benzoxazol-4-yl) hexyl group, 6- (2,3-dihydro-2-oxo-benzoxazole) -5-yl) hexyl group, 6- (2,3-dihydro-2-oxo-benzoxazol-6-yl) hexyl group, 6- (2,3-dihydro-2-oxo-benzoxazole-7-yl) Hexyl group etc. can be mentioned.

  As the benzoxazolyl group, for example, benzoxazol-2-yl group, benzoxazol-4-yl group, benzoxazol-5-yl group, benzoxazol-6-yl group, benzoxazol-7-yl group and the like can be mentioned. It can be mentioned.

  Examples of the oxazolyl C1-6 alkyl group (wherein at least one group selected from the group consisting of a phenyl group and a C1-6 alkyl group may be substituted on the oxazole ring) include, for example, oxazole-2- Ylmethyl group, oxazol-4-ylmethyl group, oxazol-5-ylmethyl group, 2- (oxazol-2-yl) ethyl group, 1- (oxazol-4-yl) ethyl group, 3- (oxazol-5-yl) group Propyl, 4- (oxazol-2-yl) butyl, 5- (oxazol-4-yl) pentyl, 6- (oxazol-5-yl) hexyl, 2-methyl-3- (oxazole-2-) (I) propyl group, 1,1-dimethyl-2- (oxazol-5-yl) ethyl group, (4-methyloxazol-2-yl) methyl group, 5-methyloxazol-2-yl) methyl group, (4-ethyloxazol-2-yl) methyl group, (5-ethyloxazol-2-yl) methyl group, (4-n-propyloxazol-2-yl) Methyl group, (5-n-propyloxazol-2-yl) methyl group, (4-n-butyloxazol-2-yl) methyl group, (5-n-butyloxazol-2-yl) methyl group, (4 -N-pentyloxazol-2-yl) methyl group, (5-n-pentyloxazol-2-yl) methyl group, (4-n-hexyloxazol-2-yl) methyl group, (5-n-hexyl oxazole) -2-yl) methyl group, 2- (oxazol-4-yl) ethyl group, 2- (oxazol-5-yl) ethyl group, 2- (4-methyl oxazol-2-yl) 2) Ethyl group, 2- (5-methyloxazol-2-yl) ethyl group, 2- (4-ethyloxazol-2-yl) ethyl group, 2- (5-ethyloxazol-2-yl) ethyl group, 2 -(4-n-propyloxazol-2-yl) ethyl group, 2- (5-n-propyloxazol-2-yl) ethyl group, 2- (4-n-butyloxazol-2-yl) ethyl group, 2- (5-n-butyloxazol-2-yl) ethyl group, 2- (4-n-pentyloxazol-2-yl) ethyl group, 2- (5-n-pentyloxazol-2-yl) ethyl group , 2- (4-n-hexyloxazol-2-yl) ethyl group, 2- (5-n-hexyloxazol-2-yl) ethyl group, 3- (oxazol-2-yl) propyl group, 3- ( Oxazole 4-yl) propyl group, 3- (4-methyloxazol-2-yl) propyl group, 3- (5-methyloxazol-2-yl) propyl group, 3- (4-ethyloxazol-2-yl) group Propyl group, 3- (5-ethyloxazol-2-yl) propyl group, 3- (4-n-propyloxazol-2-yl) propyl group, 3- (5-n-propyloxazol-2-yl) propyl group Group, 3- (4-n-butyloxazol-2-yl) propyl group, 3- (5-n-butyloxazol-2-yl) propyl group, 3- (4-n-pentyloxazol-2-yl) group Propyl group, 3- (5-n-pentyloxazol-2-yl) propyl group, 3- (4-n-hexyloxazol-2-yl) propyl group, 3- (5-n-hexyl oxazoe group 4- (Oxazol-4-yl) butyl group, 4- (oxazol-5-yl) butyl group, 4- (4-methyloxazol-2-yl) butyl group, 4- (4-yl) propyl group 5-methyloxazol-2-yl) butyl group, 4- (4-ethyloxazol-2-yl) butyl group, 4- (5-ethyloxazol-2-yl) butyl group, 4- (4-n-propyl) group Oxazol-2-yl) butyl group, 4- (5-n-propyloxazol-2-yl) butyl group, 4- (4-n-butyloxazol-2-yl) butyl group, 4- (5-n-) Butyloxazol-2-yl) butyl group, 4- (4-n-pentyloxazol-2-yl) butyl group, 4- (5-n-pentyloxazol-2-yl) butyl group, 4- (4-n) -Hexyl oxa -L-2-yl) butyl group, 4- (5-n-hexyloxazol-2-yl) butyl group, 5- (oxazol-2-yl) pentyl group, 5- (oxazol-5-yl) pentyl group Group, 6- (oxazol-2-yl) hexyl group, 6- (oxazol-4-yl) hexyl group, (5-phenyloxazol-2-yl) methyl group, (2-phenyloxazol-4-yl) methyl Group, (2-phenyloxazol-5-yl) methyl group, 2- (5-phenyloxazol-2-yl) ethyl group, 2- (2-phenyloxazol-4-yl) ethyl group, 2- (2- Phenyloxazol-5-yl) ethyl group, 3- (5-phenyloxazol-2-yl) propyl group, 3- (2-phenyloxazol-4-yl) propyl group, 3- ( 2-phenyloxazol-5-yl) propyl group, 4- (5-phenyloxazol-2-yl) butyl group, 4- (2-phenyloxazol-4-yl) butyl group, 4- (2-phenyloxazole- 5-yl) butyl group, 5- (5-phenyloxazol-2-yl) pentyl group, 5- (2-phenyloxazol-4-yl) pentyl group, 5- (2-phenyloxazol-5-yl) pentyl group Group, (2-phenyl-4-methyloxazol-5-yl) methyl group, (2,4-dimethyloxazol-5-yl) methyl group, (2,5-diphenyloxazol-4-yl) methyl group, etc. An oxazolyl C.sub.1-6 alkyl group (on the oxazole ring, one to three groups selected from the group consisting of a phenyl group and a C.sub.1-6 alkyl group are substituted, Good) can be mentioned.

  As a tetrazolyl group [a phenyl group which may have a C1-6 alkyl group or a halogen atom may be substituted on a tetrazole ring], for example, a 5- (1H) -tetrazolyl group, 1-methyl- and the like can be mentioned. 5- (1H) -tetrazolyl group, 1-ethyl-5- (1H) -tetrazolyl group, 1-n-propyl-5- (1H) -tetrazolyl group, 1-isopropyl-5- (1H) -tetrazolyl group, 1-n-butyl-5- (1H) -tetrazolyl group, 1- (2-methylpropyl) -5- (1H) -tetrazolyl group, 1-n-pentyl-5- (1H) -tetrazolyl group, 1- n-hexyl-5- (1H) -tetrazolyl group, 1-phenyl-5- (1H) -tetrazolyl group, 1- (4-chlorophenyl) -5- (1H) -tetrazolyl group, 1- (4-full) Rophenyl) -5- (1H) -tetrazolyl group, 1- (4-bromophenyl) -5- (1H) -tetrazolyl group, 1- (3,4-difluorophenyl) -5- (1H) -tetrazolyl group, Tetrazolyl groups such as 1- (3,4-dichlorophenyl) -5- (1H) -tetrazolyl group, 1- (3,4,5-trichlorophenyl) -5- (1H) -tetrazolyl group (on the tetrazole ring And C.sub.1-6 alkyl group or a phenyl group which may have 1 to 3 halogen atoms as the substituent may be mentioned.

  The C1-8 alkyl group is a linear or branched alkyl group having 1 to 8 carbon atoms, and examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, and an n- group. Butyl group, isobutyl group, tert-butyl group, sec-butyl group, n-pentyl group, neopentyl group, n-hexyl group, isohexyl group, 3-methylpentyl group, n-heptyl group, 6-methylheptyl group, n -Octyl group, 3,5-dimethylhexyl group etc. can be mentioned.

  As a halogen substituted C1-6 alkyl group, for example, fluoromethyl group, difluoromethyl group, trifluoromethyl group, chloromethyl group, dichloromethyl group, trichloromethyl group, bromomethyl group, dibromomethyl group, dichlorofluoromethyl group, 2 , 2,2-trifluoroethyl group, pentafluoroethyl group, 2-chloroethyl group, 3,3,3-trifluoropropyl group, heptafluoropropyl group, heptafluoroisopropyl group, 3-chloropropyl group, 2-chloro Propyl group, 3-bromopropyl group, 4,4,4-trifluorobutyl group, 4,4,4,3,3-pentafluorobutyl group, 4-chlorobutyl group, 4-bromobutyl group, 2-chlorobutyl group, 5,5,5-trifluoropentyl group, 5-chloropentyl group, 6,6,6- Hexyl group trifluoroacetic, halogen atoms such as 6-chloro-hexyl group can be given one to seven substituted with C1~6 alkyl.

  The C1-6 alkoxycarbonyl-C1-6 alkyl group is a C1-6 alkyl group as defined above which is substituted by the previously defined C1-6 alkoxycarbonyl group, and examples thereof include a methoxycarbonylmethyl group and ethoxycarbonylmethyl. Group, propoxycarbonylmethyl group, isopropoxycarbonylmethyl group, n-butoxycarbonylmethyl group, tert-butoxycarbonylmethyl group, pentoxy carbonylmethyl group, n-hexyloxycarbonylmethyl group, 2- (methoxycarbonyl) ethyl group, 2- (Ethoxycarbonyl) ethyl, 2- (1-propoxycarbonyl) ethyl, 2- (isopropoxycarbonyl) ethyl, 2- (n-butoxycarbonyl) ethyl, 2- (tert-butoxycarbonyl) ethyl Group 2- (2 Pentoxycarbonyl) ethyl group, 2- (n-hexyloxycarbonyl) ethyl group, 3- (methoxycarbonyl) propyl group, 3- (ethoxycarbonyl) propyl group, 3- (1-propoxycarbonyl) propyl group, 3- (Isopropoxycarbonyl) propyl group, 3- (n-butoxycarbonyl) propyl group, 3- (tert-butoxycarbonyl) propyl group, 3- (3-pentoxycarbonyl) propyl group, 3- (n-hexyloxycarbonyl) ) Propyl, 4- (methoxycarbonyl) butyl, 4- (ethoxycarbonyl) butyl, 4- (1-propoxycarbonyl) butyl, 4- (isopropoxycarbonyl) butyl, 4- (n-butoxycarbonyl) ) Butyl group, 4- (tert-butoxycarbonyl) butyl group 5- (methoxycarbonyl) pentyl group, 5- (ethoxycarbonyl) pentyl group, 5- (propoxycarbonyl) pentyl group, 5- (isopropoxycarbonyl) pentyl group, 5- (n-butoxycarbonyl) pentyl group, 5- (Tert-butoxycarbonyl) pentyl group, 6- (methoxycarbonyl) hexyl group, 6- (ethoxycarbonyl) hexyl group, 6- (propoxycarbonyl) hexyl group, 6- (isopropoxycarbonyl) hexyl group, 6- (n) And -butoxycarbonyl) hexyl group, 6- (tert-butoxycarbonyl) hexyl group and the like can be mentioned.

  The C3-8 cycloalkyl group is a 3-, 8-, 5-, 6-, 7-, or 8-membered cyclic alkyl group having 3 to 8 carbon atoms. For example, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, 3,4-dimethylcyclopentyl group, 3,3-dimethylcyclohexyl group and the like can be mentioned.

  Phenyl C1-6 alkyl group (wherein at least one of the groups selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group on the phenyl ring The term “optionally substituted” means an unsubstituted phenyl C1-6 alkyl group, and a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted group on the phenyl ring constituting those groups. A group selected from the group consisting of unsubstituted C1-6 alkoxy groups, which is substituted by 1 to 5, preferably 1 to 3 groups, and examples thereof include benzyl group, 1-phenethyl group and 2-phenethyl group Group, 3-phenylpropyl group, 2-phenylpropyl group, 4-phenylbutyl group, 5-phenylpentyl group, 4-phenylpentyl group 6-phenylhexyl group, 2-fluorobenzyl group, 3-fluorobenzyl group, 4-fluorobenzyl group, 2-chlorobenzyl group, 3-chlorobenzyl group, 4-chlorobenzyl group, 2-bromobenzyl group, 3- Bromobenzyl, 4-bromobenzyl, 2-iodobenzyl, 3-iodobenzyl, 4-iodobenzyl, 2,3-difluorobenzyl, 3,4-difluorobenzyl, 3,5-difluorobenzyl Group, 2,4-difluorobenzyl group, 2,6-difluorobenzyl group, 2,3-dichlorobenzyl group, 3,4-dichlorobenzyl group, 3,5-dichlorobenzyl group, 2,4-dichlorobenzyl group, 2,6-dichlorobenzyl group, 2-fluoro-4-bromobenzyl group, 4-chloro-3-fluorobenzyl group, 2,3,3, -Trichlorobenzyl group, 3,4,5-trifluorobenzyl group, 2,4,6-trichlorobenzyl group, 4-isopropylbenzyl group, 4-n-butylbenzyl group, 4-methylbenzyl group, 2-methylbenzyl group Group, 3-methylbenzyl group, 2,4-dimethylbenzyl group, 2,3-dimethylbenzyl group, 2,6-dimethylbenzyl group, 3,5-dimethylbenzyl group, 2,5-dimethylbenzyl group, 2, 4,6-trimethylbenzyl group, 3,5-ditrifluoromethylbenzyl group, 2,3,4,5,6-pentafluorobenzyl group, 4-isopropoxybenzyl group, 4-n-butoxybenzyl group, 4- Methoxybenzyl group, 2-methoxybenzyl group, 3-methoxybenzyl group, 2,4-dimethoxybenzyl group, 2,3-dimethoxybenzyl group, 2 , 6-Dimethoxybenzyl group, 3,5-dimethoxybenzyl group, 2,5-dimethoxybenzyl group, 2,4,6-trimethoxybenzyl group, 3,5-ditrifluoromethoxybenzyl group, 2-isopropoxybenzyl group , 3-chloro-4-methoxybenzyl group, 2-chloro-4-trifluoromethoxybenzyl group, 3-methyl-4-fluorobenzyl group, 4-bromo-3-trifluoromethylbenzyl group, 2-trifluoromethyl Benzyl, 3-trifluoromethylbenzyl, 4-trifluoromethylbenzyl, 2-pentafluoroethylbenzyl, 3-pentafluoroethylbenzyl, 4-pentafluoroethylbenzyl, 2-trifluoromethoxybenzyl , 3-Trifluoromethoxybenzyl group, 4-Trifluoromethoxy Benzyl group, 2-pentafluoroethoxybenzyl group, 3-pentafluoroethoxybenzyl group, 4-pentafluoroethoxybenzyl group, 2- (2-trifluoromethylphenyl) ethyl group, 2- (3-trifluoromethylphenyl) Ethyl group, 2- (4-trifluoromethylphenyl) ethyl group, 2- (2-trifluoromethoxyphenyl) ethyl group, 3-trifluoromethoxyphenyl) ethyl group, 2- (4-trifluoromethoxyphenyl) ethyl Group, 2- (2-pentafluoroethoxyphenyl) ethyl group, 2- (3-pentafluoroethoxyphenyl) ethyl group, 2- (4-pentafluoroethoxyphenyl) ethyl group, 3- (2-trifluoromethylphenyl) group ) Propyl group, 3- (3-trifluoromethylphenyl) propy Group, 3- (4-trifluoromethylphenyl) propyl group, 3- (2-trifluoromethoxyphenyl) propyl group, 3- (3-trifluoromethoxyphenyl) propyl group, 3- (4-trifluoromethoxyphenyl) group ) Propyl group, 3- (3-pentafluoroethoxyphenyl) propyl group, 3- (4-pentafluoroethoxyphenyl) propyl group, 4- (3-pentafluoroethoxyphenyl) butyl group, 5- (4-trifluoro) Methylphenyl) pentyl group, 4- (4-trifluoromethylphenyl) pentyl group, 4- (4-trifluoromethoxyphenyl) pentyl group, 6- (3-trifluoromethylphenyl) hexyl group, 6- (4- (4-trifluoromethylphenyl) hexyl group) Trifluoromethylphenyl) hexyl group, 6- (4-trifluoromethoxyphenyl) hexene A sil group etc. can be mentioned.

  Phenyl group (in the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group, a halogen substituted or unsubstituted C1-6 alkoxy group, a C1-6 alkanoyl group, a carboxyl group, a C1-6 alkoxycarbonyl group And a group selected from the group consisting of phenyl C1-6 alkoxycarbonyl group, carbamoyl group, C1-6 alkyl carbamoyl group, aminosulfonyl group and morpholino group may be substituted with 1 to 3), for example, Phenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 2-bromophenyl group, 3-bromophenyl group, 4- Bromophenyl group, 2-iodophenyl group, 3-iodophenyl group, -Iodophenyl group, 2,3-difluorophenyl group, 3,4-difluorophenyl group, 3,5-difluorophenyl group, 2,4-difluorophenyl group, 2,6-difluorophenyl group, 2,3-dichlorophenyl group Group, 3,4-dichlorophenyl group, 3,5-dichlorophenyl group, 2,4-dichlorophenyl group, 2,6-dichlorophenyl group, 3,4,5-trifluorophenyl group, 3,4,5-trichlorophenyl group 2,4,6-trifluorophenyl group, 2,4,6-trichlorophenyl group, 2-fluoro-4-bromophenyl group, 4-chloro-3-fluorophenyl group, 2,3,4-trichlorophenyl group Group, 4-isopropylphenyl group, 4-n-butylphenyl group, 2,4-dimethylphenyl group, 2,3-dimethylphenyl group 2,6-dimethylphenyl group, 3,5-dimethylphenyl group, 2,5-dimethylphenyl group, 2,4,6-trimethylphenyl group, 3,5-ditrifluoromethylphenyl group, 4-n-butoxyphenyl group Group, 2,4-dimethoxyphenyl group, 2,3-dimethoxyphenyl group, 2,6-dimethoxyphenyl group, 3,5-dimethoxyphenyl group, 2,5-dimethoxyphenyl group, 3,5-ditrifluoromethoxyphenyl group Group, 3-chloro-4-methoxyphenyl group, 2-chloro-4-trifluoromethoxyphenyl group, 3-methyl-4-fluorophenyl group, 4-bromo-3-trifluoromethylphenyl group, 2-methylphenyl Group, 3-methylphenyl group, 4-methylphenyl group, 2-trifluoromethylphenyl group, 3-trifluoromethyl Phenyl, 4-trifluoromethylphenyl, 2-pentafluoroethylphenyl, 3-pentafluoroethylphenyl, 4-pentafluoroethylphenyl, 2-isopropylphenyl, 3-isopropylphenyl, 2-tert -Butylphenyl group, 3-tert-butylphenyl group, 4-tert-butylphenyl group, 2-sec-butylphenyl group, 3-sec-butylphenyl group, 4-sec-butylphenyl group, 2-n-hepta Fluoropropylphenyl group, 3-n-heptafluoropropylphenyl group, 4-n-heptafluoropropylphenyl group, 4-n-pentylphenyl group, 4-n-hexylphenyl group, 2-methoxyphenyl group, 3-methoxy Phenyl group, 4-methoxyphenyl group, 2,3-dimethoxy Phenyl group, 3-fluoro-2-methoxyphenyl group, 2-fluoro-3-methoxyphenyl group, 2-chloro-4-methoxyphenyl group, 2,3,4-trimethoxyphenyl group, 3,4,5- Trimethoxyphenyl group, 2,4,6-trimethoxyphenyl group, 2-trifluoromethoxyphenyl group, 3-trifluoromethoxyphenyl group, 4-trifluoromethoxyphenyl group, 2-pentafluoroethoxyphenyl group, 3- Pentafluoroethoxyphenyl group, 4-pentafluoroethoxyphenyl group, 2-isopropoxyphenyl group, 3-isopropoxyphenyl group, 4-isopropoxyphenyl group, 2-tert-butoxyphenyl group, 3-tert-butoxyphenyl group , 4-tert-butoxyphenyl group, 2-sec-butokiki Phenyl group, 3-sec-butoxyphenyl group, 4-sec-butoxyphenyl group, 2-n-heptafluoropropoxyphenyl group, 3-n-heptafluoropropoxyphenyl group, 4-n-heptafluoropropoxyphenyl group, 4 -Pentoxyphenyl group, 4-hexyloxyphenyl group, 2-famylphenyl group, 3-formylphenyl group, 4-formylphenyl group, 2-acetylphenyl group, 3-acetylphenyl group, 4-acetylphenyl group, 2- Propionylphenyl group, 3-propionylphenyl group, 4-propionylphenyl group, 2-butyrylphenyl group, 3-butyrylphenyl group, 4-butyrylphenyl group, 2-pentanoylphenyl group, 3-pentanoylphenyl group , 4-pentanoylphenyl group, 2-hexanoylfe Group, 3-hexanoylphenyl group, 4-hexanoylphenyl group, 2-methoxycarbonylphenyl group, 3-methoxycarbonylphenyl group, 4-methoxycarbonylphenyl group, 2-ethoxycarbonylphenyl group, 3-ethoxycarbonylphenyl group Group, 4-ethoxycarbonylphenyl group, 2-propoxycarbonylphenyl group, 3-propoxycarbonylphenyl group, 4-propoxycarbonylphenyl group, 2-butoxycarbonylphenyl group, 3-butoxycarbonylphenyl group, 4-butoxycarbonylphenyl group , 2-tert-butoxycarbonylphenyl group, 3-tert-butoxycarbonylphenyl group, 4-tert-butoxycarbonylphenyl group, 2-pentoxy carbonylphenyl group, 3-pentoxycarbo -Phenyl, 4-pentoxycarbonylphenyl, 2-hexyloxycarbonylphenyl, 3-hexyloxycarbonylphenyl, 4-hexyloxycarbonylphenyl, 2-benzyloxycarbonylphenyl, 3-benzyloxycarbonylphenyl , 4-benzyloxycarbonylphenyl group, 2-carboxylphenyl group, 3-carboxylphenyl group, 4-carboxylphenyl group, 2-aminosulfonylphenyl group, 3-aminosulfonylphenyl group, 4-aminosulfonylphenyl group, 2- Carbamoylphenyl group, 3-carbamoylphenyl group, 4-carbamoylphenyl group, 2-methylcarbamoylphenyl group, 3-methylcarbamoylphenyl group, 4-methylcarbamoylphenyl group, 2-ethyl Carbamoylphenyl group, 3-ethylcarbamoylphenyl group, 4-ethylcarbamoylphenyl group, 2-dimethylcarbamoylphenyl group, 3-dimethylcarbamoylphenyl group, 4-dimethylcarbamoylphenyl group, 2-diethylcarbamoylphenyl group, 3-diethylcarbamoyl group A phenyl group, 4-diethylcarbamoylphenyl group, 4-morpholinophenyl group, 3-morpholinophenyl group, 4-morpholinophenyl group etc. can be mentioned.

  A C1-6 alkyl carbamoyl group is a group in which one or two hydrogens constituting a carbamoyl (-CONH2) group are substituted with a C1-6 alkyl group as defined above, for example, N-methyl Carbamoyl group, N, N-dimethylcarbamoyl group, n-ethylcarbamoyl group, N-n-propylcarbamoyl group, N-isopropylcarbamoyl group, N-n-butylcarbamoyl group, N-tert-butylcarbamoyl group, N-n -Pentylcarbamoyl group, N-n-hexylcarbamoyl group, N-methyl-N-ethylcarbamoyl group, N-methyl-N-n-propylcarbamoyl group, N-methyl-N-isopropylcarbamoyl group, N-methyl-N -N-butylcarbamoyl group, N-methyl-N-tert-butylcarbamoyl group, N-methyl- -N-pentylcarbamoyl group, N-methyl-N-n-hexylcarbamoyl group, N-ethyl-N-isopropylcamoyl group, N-ethyl-N-tert-butylcarbamoyl group, N-propyl-N-tert- Examples include butyl carbamoyl group, N-isopropyl-N-tert-butyl carbamoyl group and the like.

  Phenyl group (in which at least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group is substituted on a phenyl ring; And the like) is selected from the group consisting of unsubstituted phenyl group and the halogen atom as defined above, halogen substituted or unsubstituted C1-6 alkyl group and halogen substituted or unsubstituted C1-6 alkoxy A phenyl group having 1 to 5, preferably 1 to 3 substituents, such as phenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3 -Chlorophenyl group, 4-chlorophenyl group, 2-bromophenyl group, 3-bromophenyl group, 4-bromophenyl group 2-iodophenyl group, 3-iodophenyl group, 4-iodophenyl group, 2,3-difluorophenyl group, 3,4-difluorophenyl group, 3,5-difluorophenyl group, 2,4-difluorophenyl group, 2,6-Difluorophenyl group, 2,3-dichlorophenyl group, 3,4-dichlorophenyl group, 3,5-dichlorophenyl group, 2,4-dichlorophenyl group, 2,6-dichlorophenyl group, 2,3,4-triphenyl Fluorophenyl group, 3,4,5-trichlorophenyl group, 2,4,6-trifluorophenyl group, 2,4,6-trichlorophenyl group, 2-fluoro-4-bromophenyl group, 4-chloro-3 -Fluorophenyl group, 2,3,4-trichlorophenyl group, 3,4,5-trifluorophenyl group, 2,3,4,5,6-penta Fluorophenyl, 2,4,6-trimethylphenyl, 4-n-butylphenyl, 2,4-dimethylphenyl, 2,3-dimethylphenyl, 2,6-dimethylphenyl, 3,5-dimethyl Phenyl, 2,5-dimethylphenyl, 3,5-ditrifluoromethylphenyl, 4-n-butoxyphenyl, 2,4-dimethoxyphenyl, 2,3-dimethoxyphenyl, 2,6-dimethoxy Phenyl group, 3,5-dimethoxyphenyl group, 2,5-dimethoxyphenyl group, 2,4,6-trimethoxyphenyl group, 3,5-ditrifluoromethoxyphenyl group, 3-chloro-4-methoxyphenyl group, 2-chloro-4-trifluoromethoxyphenyl group, 3-methyl-4-fluorophenyl group, 4-bromo-3-trifluoromethyl group 2-phenylphenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2-methyl-3-chlorophenyl, 3-methyl-4-chlorophenyl, 2-chloro-4-methylphenyl, 2 -Methyl-3-fluorophenyl group, 2-trifluoromethylphenyl group, 3-trifluoromethylphenyl group, 4-trifluoromethylphenyl group, 2-pentafluoroethylphenyl group, 3-pentafluoroethylphenyl group, 4 -Pentafluoroethylphenyl group, 2-isopropylphenyl group, 3-isopropylphenyl group, 4-isopropylphenyl group, 2-tert-butylphenyl group, 3-tert-butylphenyl group, 4-tert-butylphenyl group, 2 -Sec-butylphenyl group, 3-sec-butylphenyl group 4-sec-butylphenyl group, 2-n-heptafluoropropylphenyl group, 3-n-heptafluoropropylphenyl group, 4-n-heptafluoropropylphenyl group, 4-pentylphenyl group, 4-hexylphenyl group, 2-methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 3-chloro-2-methoxyphenyl group, 2-fluoro-3-methoxyphenyl group, 2-fluoro-4-methoxyphenyl group, 3, 4-dimethoxyphenyl group, 2-trifluoromethoxyphenyl group, 3-trifluoromethoxyphenyl group, 4-trifluoromethoxyphenyl group, 3-fluoro-2-trifluoromethoxyphenyl group, 2-fluoro-3-trifluoro Methoxyphenyl group, 3-fluoro-4-trifluoromethoxy , 3-chloro-2-trifluoromethoxyphenyl group, 2-chloro-3-trifluoromethoxyphenyl group, 3-chloro-4-trifluoromethoxyphenyl group, 2-pentafluoroethoxyphenyl group, 3-pentacene group Fluoroethoxyphenyl group, 4-pentafluoroethoxyphenyl group, 3-chloro-2-pentafluoroethoxyphenyl group, 2-chloro-3-pentafluoroethoxyphenyl group, 3-chloro-4-pentafluoroethoxyphenyl group, 2 -Isopropoxyphenyl group, 3-isopropoxyphenyl group, 4-isopropoxyphenyl group, 2-tert-butoxyphenyl group, 3-tert-butoxyphenyl group, 4-tert-butoxyphenyl group, 2-sec-butoxyphenyl group Group, 3-sec-butoxyfe Group, 4-sec-butoxyphenyl group, 2-n-heptafluoropropoxyphenyl group, 3-n-heptafluoropropoxyphenyl group, 4-n-heptafluoropropoxyphenyl group, 4-n-pentoxyphenyl group, A 4-n-hexyl oxyphenyl group etc. can be mentioned.

  Phenyl C1-6 alkoxycarbonyl group (on the phenyl ring, at least a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group And 1 type may be substituted) is selected from the group consisting of a halogen atom as defined above, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group A group consisting of a phenyl C1-6 alkoxy group optionally substituted with 1 to 5, preferably 1 to 3 alkoxy groups and a carbonyl group, and examples thereof include a benzyloxycarbonyl group and a 2-phenylethoxycarbonyl group , 3-phenylpropoxycarbonyl group, 2-phenylpropoxycarbonyl group, 4-phenylbutoxy Ribonyl group, 5-phenyl pentoxy carbonyl group, 4-phenyl pentoxy carbonyl group, 6-phenyl hexyl oxycarbonyl group, 2- fluoro benzyl oxycarbonyl group, 3- fluoro benzyl oxycarbonyl group, 4- fluoro benzyl oxycarbonyl group , 2- (2-fluorophenyl) ethoxycarbonyl group, 2- (3-fluorophenyl) ethoxycarbonyl group, 2- (4-fluorophenyl) ethoxycarbonyl group, 2-chlorobenzyloxycarbonyl group, 3-chlorobenzyloxy Carbonyl group, 4-chlorobenzyloxycarbonyl group, 2-fluoro-4-bromobenzyloxycarbonyl group, 4-chloro-3-fluorobenzyloxycarbonyl group, 2,3,4-trichlorobenzyloxycarbonyl group, 3 4,5-trifluorobenzyloxycarbonyl group, 2,3,4,5,6-pentafluorobenzyloxycarbonyl group, 2,4,6-trichlorobenzyloxycarbonyl group, 4-isopropylbenzyloxycarbonyl group, 4- n-Butylbenzyloxycarbonyl group, 4-methylbenzyloxycarbonyl group, 2-methylbenzyloxycarbonyl group, 3-methylbenzyloxycarbonyl group, 2,4-dimethylbenzyloxycarbonyl group, 2,3-dimethylbenzyloxycarbonyl group Group, 2,6-dimethylbenzyloxycarbonyl group, 3,5-dimethylbenzyloxycarbonyl group, 2,5-dimethylbenzyloxycarbonyl group, 2,4,6-trimethylbenzyloxycarbonyl group, 3,5-ditrifluoro Methyl benzyl Oxycarbonyl group, 4-isopropoxybenzyloxycarbonyl group, 4-n-butoxybenzyloxycarbonyl group, 4-methoxybenzyloxycarbonyl group, 2-methoxybenzyloxycarbonyl group, 3-methoxybenzyloxycarbonyl group, 2,4 -Dimethoxybenzyloxycarbonyl group, 2,3-dimethoxybenzyloxycarbonyl group, 2,6-dimethoxybenzyloxycarbonyl group, 3,5-dimethoxybenzyloxycarbonyl group, 2,5-dimethoxybenzyloxycarbonyl group, 2,4 , 6-trimethoxybenzyloxycarbonyl group, 3,5-ditrifluoromethoxybenzyloxycarbonyl group, 2-isopropoxybenzyloxycarbonyl group, 3-chloro-4-methoxybenzyloxycarbonyl group 2-chloro-4-trifluoromethoxybenzyloxycarbonyl group, 3-methyl-4-fluorobenzyloxycarbonyl group, 4-bromo-3-trifluoromethylbenzyloxycarbonyl group, 2- (2-chlorophenyl) ethoxycarbonyl group , 2- (3-chlorophenyl) ethoxycarbonyl group, 2- (4-chlorophenyl) ethoxycarbonyl group, 2-trifluoromethylbenzyloxycarbonyl group, 3-trifluoromethylbenzyloxycarbonyl group, 4-trifluoromethylbenzyloxy Carbonyl group, 2-trifluoromethoxybenzyloxycarbonyl group, 3-trifluoromethoxybenzyloxycarbonyl group, 4-trifluoromethoxybenzyloxycarbonyl group, 2- (2-trifluoromethylphenyl) Ethoxycarbonyl group, 2- (3-trifluoromethylphenyl) ethoxycarbonyl group, 2- (4-trifluoromethylphenyl) ethoxycarbonyl group, 2- (2-trifluoromethoxyphenyl) ethoxycarbonyl group, 2- (3 -Trifluoromethoxyphenyl) ethoxycarbonyl group, 2- (4-trifluoromethoxyphenyl) ethoxycarbonyl group, 3- (2-trifluoromethylphenyl) propoxycarbonyl group, 3- (3-trifluoromethylphenyl) propoxycarbonyl group Group, 3- (4-trifluoromethylphenyl) propoxycarbonyl group, 3- (2-trifluoromethylphenyl) propoxycarbonyl group, 3- (3-trifluoromethoxyphenyl) propoxycarbonyl group, 3- (4-trichloromethoxyphenyl) propoxycarbonyl group Fluorometh Xyphenyl) propoxycarbonyl group, 4- (3-trifluoromethylphenyl) butoxycarbonyl group, 5- (4-trifluoromethylphenyl) pentoxy carbonyl group, 4- (4-trifluoromethylphenyl) pentoxy carbonyl group, 4- (4-trifluoromethoxyphenyl) pentoxycarbonyl group, 6- (3-trifluoromethylphenyl) hexyloxycarbonyl group, 6- (4-trifluoromethylphenyl) hexyloxycarbonyl group, 6- (4-trifluoromethylphenyl) hexyloxycarbonyl group A trifluoromethoxyphenyl) hexyl oxycarbonyl group etc. can be mentioned.

  Examples of the phenyl C3-6 alkenyloxycarbonyl group (wherein at least one halogen-substituted or unsubstituted C1-6 alkyl group may be substituted on the phenyl ring) include an unsubstituted phenyl group and a halogen-substituted group. A group selected from the group consisting of unsubstituted C1-6 alkyl groups is composed of a substituted or unsubstituted phenyl group having 1 to 3 carbon atoms, an alkenyloxy group having 1 to 3 carbon atoms and 1 to 3 double bonds, and a carbonyl group And includes both a trans form and a cis form. As such a group, for example, 3-phenyl-2-propenyloxycarbonyl group (conventional name: cinnamyloxycarbonyl group), 4-phenyl-2-butenyloxycarbonyl group, 4-phenyl-3-butenyl group Oxycarbonyl group, 5-phenyl-2-pentenyloxycarbonyl group, 5-phenyl-4-pentenyloxycarbonyl group, 5-phenyl-3-pentenyloxycarbonyl group, 6-phenyl-5-hexenyloxycarbonyl group, 6- Phenyl-4-hexenyloxycarbonyl group, 6-phenyl-3-hexenyloxycarbonyl group, 6-phenyl-3-hexenyloxycarbonyl group, 4-phenyl-1,3-butadienyloxycarbonyl group, 6-phenyl- 1,3,5-hexatrienyloxy carbonyl group, 3- 2-methylphenyl) -2-propenyloxycarbonyl group, 3- (3-methylphenyl) -2-propenyloxycarbonyl group, 3- (4-methylphenyl) -2-propenyloxycarbonyl group, 3- (2- (2-methylphenyl) -2-propenyloxycarbonyl group Trifluoromethylphenyl) -2-propenyloxycarbonyl group, 3- (3-trifluoromethylphenyl) -2-propenyloxycarbonyl group, 3- (4-trifluoromethylphenyl) -2-propenyloxycarbonyl group, 4 -(2-trifluoromethylphenyl) -3-butenyloxycarbonyl group, 4- (3-trifluoromethylphenyl) -3-butenyloxycarbonyl group, 4- (4-trifluoromethylphenyl) -3- Butenyloxycarbonyl group, 3- (3,5-ditrifluoromethylphenyl)- -Propenyloxycarbonyl group, 3- [2,4,6-tri (trifluoromethyl) phenyl] -2-propenyloxycarbonyl group, 3- (2,4-dimethylphenyl) -2-propenyloxycarbonyl group, etc. It can be mentioned.

  The phenyl C1-6 alkylidene substituted amino group (in the phenyl ring, at least one halogen substituted or unsubstituted C1-6 alkyl group may be substituted) means a halogen substituted or unsubstituted C1-6 alkyl A C1-6 alkylidene-substituted amino group substituted by a phenyl group which may be substituted by 1 to 3 groups, and examples thereof include a benzylideneamino group, 2-phenylethylideneamino group, 3-phenylpropylideneamino group, 4- Phenylbutylideneamino group. 5-phenylpentylideneamino group, 6-phenylhexylideneamino group, 2-methylbenzylideneamino group, 2-trifluoromethylbenzylideneamino group, 3-methylbenzylideneamino group, 3-trifluoromethylbenzylideneamino group, 4 -Methylbenzylideneamino group, 4-trifluoromethylbenzylideneamino group, 3,4-dimethylbenzylideneamino group, 3,4,5-trimethylbenzylideneamino group, 3,5-ditrifluoromethylbenzylideneamino group, etc. it can.

  The phenoxy group (on the phenyl ring, at least one halogen-substituted or unsubstituted C1-6 alkyl group may be substituted) means an unsubstituted phenoxy group or a halogen-substituted or unsubstituted group as defined above A phenoxy group in which 1 to 3 C1-6 alkyl groups are substituted, and examples thereof include phenoxy group, 2-methylphenoxy group, 3-methylphenoxy group, 4-methylphenoxy group, 2-ethylphenoxy group, 3-ethyl group Siphenoxy group, 4-ethylphenoxy group, 4-n-propylphenoxy group, 4-tert-butylphenoxy group, 4-n-butylphenoxy group, 2-trifluoromethylphenoxy group, 3-trifluoromethylphenoxy group, 4-trifluoromethylphenoxy group, 2-pentafluoroethyl phenoxy group, 3-pentafu Oroethyl phenoxy group, 2,3-dimethyl phenoxy group, 3,4,5-trimethyl phenoxy group, 4-n-pentyl phenoxy group, 4-n-hexyl phenoxy group, 3,5-ditrifluoromethyl phenoxy group, etc. It can be mentioned.

  The phenylamino group (on the phenyl ring, at least one halogen-substituted or unsubstituted C1-6 alkyl group may be substituted) means an unsubstituted phenylamino group (alias: anilino group) or A phenylamino group substituted by 1 to 3 halogen-substituted or unsubstituted C1-6 alkyl groups as defined above, such as phenylamino, 2-methylphenylamino, 3-methylphenylamino, 4-methyl; Phenylamino group, 2-ethylphenylamino group, 3-ethylphenylamino group, 4-ethylphenylamino group, 4-propylphenylamino group, 4-tert-butylphenylamino group, 4-butylphenylamino group, 2- Trifluoromethylphenylamino group, 3-trifluoromethylphenylamino group, 4-trifluoro Ethylphenylamino group, 2-pentafluoroethylphenylamino group, 3-pentafluoroethylphenylamino group, 2,3-dimethylphenylamino group, 3,4,5-trimethylphenylamino group, 4-n-pentylphenylamino Groups, 4-n-hexylphenylamino group, 3,5-ditrifluoromethylphenylamino group and the like can be mentioned.

  The indolinyl group (at least one halogen atom may be substituted on the indoline ring) means a fluorine atom, a chlorine atom or a bromine atom which is unsubstituted or at the 2, 3, 4, 5, 6 or 7 position. Or an indolinyl group substituted by 1 to 3 iodine atoms, and examples thereof include 1-indolinyl group, 2-fluoro-1-indolinyl group, 3-bromo-1-indolinyl group, 4,5-dichloro-1-indolinyl Group, 4-fluoro-1-indolinyl group, 4,5,6-trifluoro-1-indolinyl group, 5-fluoro-1-indolinyl group, 6-fluoro-1-indolinyl group, 7-fluoro-1-indolinyl group Group, 4-chloro-1-indolinyl group, 5-chloro-1-indolinyl group, 6-chloro-1-indolinyl group, 7-chloro-1-indolinyl group, 4-bro -1-indolinyl group, 5-bromo-1-indolinyl group, 6-bromo-1-indolinyl group, 7-bromo-1-indolinyl group, 4-iodo-1-indolinyl group, 5-iodo-1-indolinyl group 6-iodo-1-indolinyl group, 7-iodo-1-indolinyl group, etc. can be mentioned.

  The isoindolinyl group (on the isoindoline ring, at least one halogen atom may be substituted) means a fluorine atom, a chlorine atom or a bromine atom which is unsubstituted or at the 1, 3, 4, 5, 6 or 7 position. An isoindolinyl group substituted by 1 to 3 atoms or an iodine atom, and examples thereof include a 2-isoindolinyl group, a 1-fluoro-2-isoindolinyl group, a 3-bromo-2-isoindolinyl group, and a 4,5-dichloro-2-yl group. Isoindolinyl group, 4,5,6-trifluoro-2-isoindolinyl group, 4-fluoro-2-isoindolinyl group, 5-fluoro-2-isoindolinyl group, 6-fluoro-2-isoindolinyl group, 7-fluoro-2-isoindolinyl group Isoindolinyl group, 4-chloro-2-isoindolinyl group, 5-chloro-2-isoindolinyl group, 6-chloro-2- Soindolinyl group, 7-chloro-2-isoindolinyl group, 4-bromo-2-isoindolinyl group, 5-bromo-2-isoindolinyl group, 6-bromo-2-isoindolinyl group, 7-bromo-2-isoindolinyl group, 4- 4- Examples thereof include iodo-2-isoindolinyl group, 5-iodo-2-isoindolinyl group, 6-iodo-2-isoindolinyl group, and 7-iodo-2-isoindolinyl group.

  The 1,2,3,4-tetrahydroquinolyl group (wherein at least one halogen atom may be substituted on the 1,2,3,4-tetrahydroquinoline ring) is unsubstituted or 2,2 A 1,2,3,4-tetrahydroquinolyl group substituted by 1 to 3 fluorine atom, chlorine atom, bromine atom or iodine atom at the 3, 4, 5, 6, 7 or 8 position, for example, 1 2,2,3,4-Tetrahydro-1-quinolyl group, 5-fluoro-1,2,3,4-tetrahydro-1-quinolyl group, 2-bromo-1,2,3,4-tetrahydro-1-quinolyl Group, 3-iodo-1,2,3,4-tetrahydro-1-quinolyl group, 4-chloro-1,2,3,4-tetrahydro-1-quinolyl group, 3,4-dichloro-1,2, 3,4-Tetrahydro-1-quinolyl group 4,5,6-triclo -1,2,3,4-tetrahydro-1-quinolyl group, 6-fluoro-1,2,3,4-tetrahydro-1-quinolyl group, 7-fluoro-1,2,3,4-tetrahydro-1 -Quinolyl group, 8-fluoro-1,2,3,4-tetrahydro-1-quinolyl group, 5-chloro-1,2,3,4-tetrahydro-1-quinolyl group, 6-chloro-1,2,5 3,4-tetrahydro-1-quinolyl group, 7-chloro-1,2,3,4-tetrahydro-1-quinolyl group, 8-chloro-1,2,3,4-tetrahydro-1-quinolyl group, 5 -Bromo-1,2,3,4-tetrahydro-1-quinolyl group, 6-bromo-1,2,3,4-tetrahydro-1-quinolyl group, 7-bromo-1,2,3,4-tetrahydro -1-quinolyl group, 8-bromo-1,2,3,4-tetra Rahydro-1-quinolyl group, 5-iodo-1,2,3,4-tetrahydro-1-quinolyl group, 6-iodo-1,2,3,4-tetrahydro-1-quinolyl group, 7-iodo-1 There may be mentioned 2,2,3,4-tetrahydro-1-quinolyl group, 8-iodo-1,2,3,4-tetrahydro-1-quinolyl group and the like.

  The 1,2,3,4-tetrahydroisoquinolinyl group (at least one halogen atom may be substituted on the 1,2,3,4-tetrahydroisoquinoline ring) is shown. And the like) means 1,2,3,4-tetrahydroisoquino which is unsubstituted or substituted by 1 to 3 fluorine atom, atom, bromine atom or iodine atom at the 1, 3, 4, 5, 6, 7 or 8 position. Ryl group, for example, 1,2,3,4-tetrahydro-2-isoquinolyl group, 1-bromo-1,2,3,4-tetrahydro-2-isoquinolyl group, 3-iodo-1,2,2,3 3,4-Tetrahydro-2-isoquinolyl group, 4-chloro-1,2,3,4-tetrahydro-2-isoquinolyl group, 3,4-dichloro-1,2,3,4-tetrahydro-2-isoquinolyl group 4,5,6-Trichloro-1,2,3,4-tetrahydro-2-isoquinolyl group, 5-fluoro-1,2,3,4-tetrahydro-2-isoquinolyl group, 6-fluoro-1,2 , 3,4-Tetrahydro-2-isoquino Group, 7-fluoro-1,2,3,4-tetrahydro-2-isoquinolyl group, 8-fluoro-1,2,3,4-tetrahydro-2-isoquinolyl group, 5-chloro-1,2,3 , 4-tetrahydro-2-isoquinolyl group, 6-chloro-1,2,3,4-tetrahydro-2-isoquinolyl group, 7-chloro-1,2,3,4-tetrahydro-2-isoquinolyl group, 8- Chloro-1,2,3,4-tetrahydro-2-isoquinolyl group, 5-bromo-1,2,3,4-tetrahydro-2-isoquinolyl group, 6-bromo-1,2,3,4-tetrahydro- 2-isoquinolyl group, 7-bromo-1,2,3,4-tetrahydro-2-isoquinolyl group, 8-bromo-1,2,3,4-tetrahydro-2-isoquinolyl group, 5-iodo-1,2 , 3,4-tetra Dro-2-isoquinolyl group, 6-iodo-1,2,3,4-tetrahydro-2-isoquinolyl group, 7-iodo-1,2,3,4-tetrahydro-2-isoquinolyl group, 8-iodo-1 And 2,3,4-tetrahydro-2-isoquinolyl and the like.

  As the C1-6 alkylene group, for example, methylene, ethylene, trimethylene, 2-methyltrimethylene, 2,2-dimethyltrimethylene, 1-methyltrimethylene, methylmethylene, ethylmethylene, tetramethylene, pentamethylene, hexamethylene And the like.

  A phenyl C1-6 alkyl group (a halogen atom on the phenyl ring; a halogen substituted or unsubstituted C1-6 alkyl group; a halogen substituted or unsubstituted C1-6 alkoxy group and a phenoxy group [substituted on the phenyl ring At least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group as a group] At least one of the groups selected from the group may be substituted, and in the C1-6 alkyl moiety, a C1-6 alkoxyimino group may be substituted) as the unsubstituted phenyl. Group or halogen atom, halogen-substituted or unsubstituted C1-6 alkyl group, halogen-substituted or unsubstituted C1-6 alkoxy group and Noxy group [on the phenyl ring, a group selected from the group consisting of a halogen atom as a substituent, a halogen-substituted or unsubstituted C1-6 alkyl group, and a halogen-substituted or unsubstituted C1-6 alkoxy group is preferably 1 to 3) Group selected from the group consisting of [1], preferably 1 to 5, preferably 1 to 3 substituted phenyl group and an alkyl group having 1 to 6 carbon atoms, For example, benzyl group, 1-phenethyl group, 2-phenethyl group, 3-phenylpropyl group, 2-phenylpropyl group, 4-phenylbutyl group, 5-phenylpentyl group, 4-phenylpentyl group, 6-phenylhexyl Group, 2-fluorobenzyl group, 3-fluorobenzyl group, 4-fluorobenzyl group, 2-chlorobenzyl group, 3-chlorobenzyl group, 4-chlorobenzyl group , 2-bromobenzyl group, 3-bromobenzyl group, 4-bromobenzyl group, 2-iodobenzyl group, 3-iodobenzyl group, 4-iodobenzyl group, 2,3-difluorobenzyl group, 3,4-difluoro Benzyl, 3,5-difluorobenzyl, 2,4-difluorobenzyl, 2,6-difluorobenzyl, 2,3-dichlorobenzyl, 3,4-dichlorobenzyl, 3,5-dichlorobenzyl 2,4-dichlorobenzyl group, 2,6-dichlorobenzyl group, 2-fluoro-4-bromobenzyl group, 4-chloro-3-fluorobenzyl group, 2,3,4-trichlorobenzyl group, 3,4 3,5-Trifluorobenzyl group, 2,3,4,5,6-pentafluorobenzyl group, 2,4,6-trichlorobenzyl group, 4-isopropyl group Group, 4-n-butylbenzyl group, 4-methylbenzyl group, 2-methylbenzyl group, 3-methylbenzyl group, 2,4-dimethylbenzyl group, 2,3-dimethylbenzyl group, 2,6-dimethyl group Benzyl group, 3,5-dimethylbenzyl group, 2,5-dimethylbenzyl group, 2,4,6-trimethylbenzyl group, 3,5-ditrifluoromethylbenzyl group, 4-isopropoxybenzyl group, 4-n- Butoxybenzyl group, 4-methoxybenzyl group, 2-methoxybenzyl group, 3-methoxybenzyl group, 2,4-dimethoxybenzyl group, 2,3-dimethoxybenzyl group, 2,6-dimethoxybenzyl group, 3,5- Dimethoxybenzyl group, 2,5-dimethoxybenzyl group, 2,4,6-trimethoxybenzyl group, 3,5-ditrifluoromethoxyben Group, 2-isopropoxybenzyl group, 3-chloro-4-methoxybenzyl group, 2-chloro-4-trifluoromethoxybenzyl group, 3-methyl-4-fluorobenzyl group, 4-bromo-3-trifluoro group Methyl benzyl group, 2-trifluoromethylbenzyl group, 3-trifluoromethylbenzyl group, 4-trifluoromethylbenzyl group, 2-pentafluoroethyl benzyl group, 3-pentafluoroethyl benzyl group, 4-pentafluoroethyl benzyl Group, 2-trifluoromethoxybenzyl group, 3-trifluoromethoxybenzyl group, 4-trifluoromethoxybenzyl group, 2-pentafluoroethoxybenzyl group, 3-pentafluoroethoxybenzyl group, 4-pentafluoroethoxybenzyl group, 2- (2-trifluoromethyl) -Yl) ethyl group, 2- (3-trifluoromethylphenyl) ethyl group, 2- (4-trifluoromethylphenyl) ethyl group, 2- (2-trifluoromethoxyphenyl) ethyl group, 2- (3-trimethyl group) Fluoromethoxyphenyl) ethyl group, 2- (4-trifluoromethoxyphenyl) ethyl group, 2- (2-pentafluoroethoxyphenyl) ethyl group, 2- (3-pentafluoroethoxyphenyl) ethyl group, 2- (4 -Pentafluoroethoxyphenyl) ethyl group, 3- (2-trifluoromethylphenyl) propyl group, 3- (3-trifluoromethylphenyl) propyl group, 3- (4-trifluoromethylphenyl) propyl group, 3- (2-trifluoromethoxyphenyl) propyl group, 3- (3-trifluoromethoxyphenyl) propyl Group, 3- (4-trifluoromethoxyphenyl) propyl group, 3- (3-pentafluoroethoxyphenyl) propyl group, 3- (4-pentafluoroethoxyphenyl) propyl group, 4- (3-pentafluoroethoxy) Phenyl) butyl group, 5- (4-trifluoromethylphenyl) pentyl group, 4- (4-trifluoromethylphenyl) pentyl group, 4- (4-trifluoromethoxyphenyl) pentyl group, 6- (3-trimethyl Fluoromethylphenyl) hexyl group, 6- (4-trifluoromethylphenyl) hexyl group, 6- (4-trifluoromethoxyphenyl) hexyl group, (4-pentafluoroethoxyphenyl) propyl group, 4- (3-penta) Fluoroethoxyphenyl) butyl group, 5- (4-trifluoromethylphenyl) pen Group, 4- (4-trifluoromethylphenyl) pentyl group, 4- (4-trifluoromethoxyphenyl) pentyl group, 6- (3-trifluoromethylphenyl) hexyl group, 6- (4-trifluoromethyl) Phenyl) hexyl group, 6- (4-trifluoromethoxyphenyl) hexyl group, 3-phenoxybenzyl group, 4-phenoxybenzyl group, 2- (4-phenoxyphenyl) ethyl group, 3- (4-phenoxyphenyl) propyl Group, 2- (4-phenoxyphenyl) propyl group, 4- (4-phenoxyphenyl) butyl group, 5- (4-phenoxyphenyl) pentyl group, 4- (4-phenoxyphenyl) pentyl group, 6- (4) -Phenoxyphenyl) hexyl group, 2-phenoxybenzyl group, 2- (3-phenoxyphenyl) ethyl 3- (2-phenoxyphenyl) propyl group, 2- (2-phenoxyphenyl) propyl group, 4- (3-phenoxyphenyl) butyl group, 5- (2-phenoxyphenyl) pentyl group, 4- (3- (3-phenoxyphenyl) propyl group Phenoxyphenyl) pentyl group, 6- (3-phenoxyphenyl) hexyl group, 4- (2-chlorophenoxy) benzyl group, 4- (3-chlorophenoxy) benzyl group, 4- (4-chlorophenoxy) benzyl group, 4- (2-trifluoromethylphenoxy) benzyl group, 4- (3-trifluoromethylphenoxy) benzyl group, 4- (4-trifluoromethylphenoxy) benzyl group, 4- (2-trifluoromethoxyphenoxy) benzyl Group, 4- (3-trifluoromethoxyphenoxy) benzyl group, 4- (4-trifluoromethoxy) Phenoxy) benzyl group, 2- [4- (4-chlorophenoxy) phenyl] ethyl group, 2- [4- (4-trifluoromethylphenoxy) phenyl] ethyl group, 3- [4- (4-chlorophenoxy) group Phenyl] propyl group, 3- [4- (4-trifluoromethylphenoxy) phenyl] propyl group, 3- [4- (4-trifluoromethoxyphenoxy) phenyl] propyl group, 2- [4- (4-chloro) Phenoxy) phenyl] propyl group, 4- [4- (4-chlorophenoxy) phenyl] butyl group, 4- [4- (4-trifluoromethylphenoxy) phenyl] butyl group, 4- [4- (4-tri-butyl] Fluoromethoxyphenoxy) phenyl] butyl group, 5- [4- (4-chlorophenoxy) phenyl] pentyl group, 4- [4- (4-chloropheno] C) Phenyl] pentyl group, 6- [4- (4-chlorophenoxy) phenyl] hexyl group, 6- [4- (4-trifluoromethylphenoxy) phenyl] hexyl group, 6- [4- (4-tri- Fluoromethoxyphenoxy) phenyl] hexyl group, (2-fluoro-4-bromophenoxy) benzyl group, (4-chloro-3-fluorophenoxy) benzyl group, (2,3,4-trichlorophenoxy) benzyl group, (3 , 4,5-Trifluorophenoxy) benzyl, (2,4,6-trichlorophenoxy) benzyl, (4-isopropylphenoxy) benzyl, (4-n-butylphenoxy) benzyl, (4-methylphenoxy) ) Benzyl group, (2-methyl phenoxy) benzyl group, (3-methyl phenoxy) benzyl group, (2, 4 Dimethylphenoxy) benzyl group, (2,3-dimethylphenoxy) benzyl group, (2,6-dimethylphenoxy) benzyl group, (3,5-dimethylphenoxy) benzyl group, (2,5-dimethylphenoxy) benzyl group, (2,4,6-trimethylphenoxy) benzyl group, (3,5-ditrifluoromethylphenoxy) benzyl group, (4-isopropoxyphenoxy) benzyl group, (4-n-butoxyphenoxy) benzyl group, (4- (Methoxyphenoxy) benzyl group, (2-methoxyphenoxy) benzyl group, (3-methoxyphenoxy) benzyl group, (2,4-dimethoxyphenoxy) benzyl group, (2,3-dimethoxyphenoxy) benzyl group, (2,6 -Dimethoxyphenoxy) benzyl group, (3,5-dimethoxyphenoxy) Benzyl group, (2,5-dimethoxyphenoxy) benzyl group, (2,4,6-trimethoxyphenoxy) benzyl group, (3,5-ditrifluoromethoxyphenoxy) benzyl group, (2-isopropoxyphenoxy) benzyl group , (3-chloro-4-methoxyphenoxy) benzyl group, (2-chloro-4-trifluoromethoxyphenoxy) benzyl group, (3-methyl-4-fluorophenoxy) benzyl group, (4-bromo-3-trile) A fluoromethyl phenoxy) benzyl group etc. can be mentioned.

  A benzoyl group (in which at least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group is substituted on a phenyl ring May be, for example, benzoyl group, 2-fluorobenzoyl group, 3-fluorobenzoyl group, 4-fluorobenzoyl group, 2,3-difluorobenzoyl group, 2,3,4,5,6-pentafluoro Benzoyl group, 3,4-difluorobenzoyl group, 2-chlorobenzoyl group, 3-chlorobenzoyl group, 4-chlorobenzoyl group, 2,3-dichlorobenzoyl group, 3,4-dichlorobenzoyl group, 2-bromobenzoyl group , 3-bromobenzoyl group, 4-bromobenzoyl group, 2,3-dibromobenzoyl group, 3,4 Dibromobenzoyl group, 2-fluoro-4-bromobenzoyl group, 4-chloro-3-fluorobenzoyl group, 2,3,4-trifluorobenzoyl group, 2,4,6-trichlorobenzoyl group, 4-isopropylbenzoyl group 4-n-Butylbenzoyl group, 2,4-dimethylbenzoyl group, 2,3-dimethylbenzoyl group, 2,6-dimethylbenzoyl group, 3,5-dimethylbenzoyl group, 2,5-dimethylbenzoyl group, 2 , 4,6-Trimethylbenzoyl group, 3,5-ditrifluoromethylbenzoyl group, 4-n-butoxybenzoyl group, 2,4-dimethoxybenzoyl group, 2,3-dimethoxybenzoyl group, 2,6-dimethoxybenzoyl group 3,5-Dimethoxybenzoyl, 2,5-dimethoxybenzoyl, 3,5-ditrif Oromethoxybenzoyl group, 3-chloro-4-methoxybenzoyl group, 2-chloro-4-trifluoromethoxybenzoyl group, 3-methyl-4-fluorobenzoyl group, 4-bromo-3-trifluoromethylbenzoyl group, 2 -Methylbenzoyl group, 3-methylbenzoyl group, 4-methylbenzoyl group, 3,4-dimethylbenzoyl group, 2-iodobenzoyl group, 3-iodobenzoyl group, 4-iodobenzoyl group, 2-trifluoromethylbenzoyl group , 3-trifluoromethylbenzoyl group, 4-trifluoromethylbenzoyl group, 2,3-ditrifluoromethylbenzoyl group, 3,4-ditrifluoromethylbenzoyl group, 2-methoxybenzoyl group, 3-methoxybenzoyl group, 4 -Methoxybenzoyl group, 2-trifluoromethoxy Benzoyl groups such as benzoyl, 3-trifluoromethoxybenzoyl, 4-trifluoromethoxybenzoyl and the like (a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted group on the phenyl ring 1 to 5, preferably 1 to 3 groups selected from the group consisting of C1-6 alkoxy groups of the above) may be mentioned.

  As a pyridyl group (on the pyridine ring, at least one halogen atom may be substituted), for example, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 2-chloropyridine-3- , 2-chloropyridin-4-yl, 2-chloropyridin-5-yl, 5-chloropyridin-2-yl, 4-chloropyridin-2-yl, 3-chloropyridin-2-yl , 2-fluoropyridin-3-yl, 2-fluoropyridin-4-yl, 2-fluoropyridin-5-yl, 5-fluoropyridin-2-yl, 4-fluoropyridine-2- , 3-fluoropyridin-2-yl group, 2-bromopyridin-3-yl group, 2-bromopyridin-4-yl group, 2-bromopyridin-5-yl group, 5-bromopyridin-2-yl group Ill , 4-bromopyridin-2-yl group, 3-bromopyridin-2-yl group, 2-bromo-4-chloropyridin-4-yl group, 2,6-dichloropyridin-4-yl group, 2,4 And pyridyl groups (such as 1 to 3 halogen atoms may be substituted on the pyridine ring) such as 6, 6-trichloropyridin-3-yl and the like.

  A phenoxy C1-6 alkyl group (on the phenyl ring, at least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group, and a halogen-substituted or unsubstituted C1-6 alkoxy group; Is optionally substituted) is a group consisting of an unsubstituted phenoxy group or a halogen-substituted or unsubstituted C1-6 alkyl group as defined above, a halogen-substituted or unsubstituted C1-6 alkoxy group and a halogen And the selected group is a group composed of a phenoxy group substituted by 1 to 5, preferably 1 to 3 and a C1 to 6 alkyl group, and examples thereof include a phenoxymethyl group, a 2-phenoxyethyl group, and a 3-phenoxy group. Propyl group, 4-phenoxybutyl group, 5-phenoxypentyl group, 6-phenoxyhexyl group, 4-fluorophenoxy Group, 2-fluoro-4-bromophenoxymethyl group, 4-chloro-3-fluorophenoxymethyl group, 2,3,4-trichlorophenoxymethyl group, 3,4,5-trichlorophenoxymethyl group, 2,4 , 6-Trichlorophenoxymethyl group, 4-isopropylphenoxymethyl group, 4-n-butylphenoxymethyl group, 4-methylphenoxymethyl group, 2-methylphenoxymethyl group, 3-methylphenoxymethyl group, 2,4-dimethyl Phenoxymethyl group, 2,3-dimethylphenoxymethyl group, 2,6-dimethylphenoxymethyl group, 3,5-dimethylphenoxymethyl group, 2,5-dimethylphenoxymethyl group, 2,4,6-trimethylphenoxymethyl group , 3,5-ditrifluoromethylphenoxymethyl, 2,3,4,5 6-pentafluorophenoxymethyl group, 4-isopropoxyphenoxymethyl group, 4-n-butoxyphenoxymethyl group, 4-methoxyphenoxymethyl group, 2-methoxyphenoxymethyl group, 3-methoxyphenoxymethyl group, 2,4- Dimethoxyphenoxymethyl group, 2,3-dimethoxyphenoxymethyl group, 2,6-dimethoxyphenoxymethyl group, 3,5-dimethoxyphenoxymethyl group, 2,5-dimethoxyphenoxymethyl group, 2,4,6-trimethoxyphenoxy Methyl group, 3,5-ditrifluoromethoxyphenoxymethyl group, 2-isopropoxyphenoxymethyl group, 3-chloro-4-methoxyphenoxymethyl group, 2-chloro-4-trifluoromethoxyphenoxymethyl group, 3-methyl- 4-Fluorophenoxy Ethyl, 4-bromo-3-trifluoromethylphenoxymethyl, 2- (4-fluorophenoxy) ethyl, 3- (4-fluorophenoxy) propyl, 4- (4-fluorophenoxy) butyl, 5 -(4-fluorophenoxy) pentyl group, 6- (4-fluorophenoxy) hexyl group, 4-chlorophenoxymethyl group, 2- (4-chlorophenoxy) ethyl group, 3- (4-chlorophenoxy) propyl group, 4- (4-chlorophenoxy) butyl group, 5- (4-chlorophenoxy) pentyl group, 6- (4-chlorophenoxy) hexyl group, 4-methylphenoxymethyl group, 2- (4-methylphenoxy) ethyl group , 3- (4-Methylphenoxy) propyl group, 4- (4-Methylphenoxy) butyl group, 5- (4-Methylphenoxy) ) Pentyl group, 6- (4-methylphenoxy) hexyl group, 4-trifluoromethylphenoxymethyl group, 2- (4-trifluoromethylphenoxy) ethyl group, 3- (4-trifluoromethylphenoxy) propyl group, 4- (4-trifluoromethylphenoxy) butyl group, 5- (4-trifluoromethylphenoxy) pentyl group, 6- (4-trifluoromethylphenoxy) hexyl group, 4-trifluoromethoxyphenoxymethyl group, 2- (4-trifluoromethoxyphenoxy) ethyl group, 3- (4-trifluoromethoxyphenoxy) propyl group, 4- (4-trifluoromethoxyphenoxy) butyl group, 5- (4-trifluoromethoxyphenoxy) pentyl group, 6- (4-trifluoromethoxyphenoxy) hexyl group, 2- 4-methoxyphenoxy) ethyl group, 3- (4-methoxyphenoxy) propyl group, 4- (4-methoxyphenoxy) butyl group, 5- (4-methoxyphenoxy) pentyl group, 6- (4-methoxyphenoxy) hexyl And the like.

  A benzoyl C1-6 alkyl group (on the phenyl ring, at least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group, and a halogen-substituted or unsubstituted C1-6 alkoxy group Is optionally substituted), for example, benzoylmethyl group, 2-benzoylethyl group, 1-benzoylethyl group, 3-benzoylpropyl group, 4-benzoylbutyl group, 5-benzoylpentyl group, 6-benzoyl group Hexyl group, 2-methyl-3-benzoylpropyl group, 1,1-dimethyl-2-benzoylethyl group, 2-fluorobenzoylmethyl group, 3-fluorobenzoylmethyl group, 4-fluorobenzoylmethyl group, 2-chlorobenzoyl Methyl group, 3-chlorobenzoyl methyl group, 4-chlorobenzoyl group Group, 2-bromobenzoylmethyl group, 3-bromobenzoylmethyl group, 4-bromobenzoylmethyl group, 2-fluoro-4-bromobenzoylmethyl group, 4-chloro-3-fluorobenzoylmethyl group, 2,3, 4-trichlorobenzoylmethyl group, 2,4,6-trichlorobenzoylmethyl group, 4-isopropylbenzoylmethyl group, 4-n-butylbenzoylmethyl group, 2,4-dimethylbenzoylmethyl group, 2,3-dimethylbenzoylmethyl group Group, 2,6-dimethylbenzoylmethyl group, 3,5-dimethylbenzoylmethyl group, 2,5-dimethylbenzoylmethyl group, 2,4,6-trimethyl benzoylmethyl group, 3,5-ditrifluoromethylbenzoylmethyl group , 2,3,4,5,6-pentafluorobenzoylmethyl group, 4 n-Butoxybenzoylmethyl group, 2,4-dimethoxybenzoylmethyl group, 2,3-dimethoxybenzoylmethyl group, 2,6-dimethoxybenzoylmethyl group, 3,5-dimethoxybenzoylmethyl group, 2,5-dimethoxybenzoyl group Methyl group, 3,5-ditrifluoromethoxybenzoylmethyl group, 3-chloro-4-methoxybenzoylmethyl group, 2-chloro-4-trifluoromethoxybenzoylmethyl group, 3-methyl-4-fluorobenzoylmethyl group, 4 -Bromo-3-trifluoromethylbenzoylmethyl group, 2-trifluoromethylbenzoylmethyl group, 3-trifluoromethylbenzoylmethyl group, 4-trifluoromethylbenzoylmethyl group, 2-trifluoromethoxybenzoylmethyl group, 3- Trifluoromethoxy Benzoylmethyl group, 4-trifluoromethoxybenzoylmethyl group, 2- (2-fluorobenzoyl) ethyl group, 2- (3-fluorobenzoyl) ethyl group, 2- (4-fluorobenzoyl) ethyl group, 2- (2) -Chlorobenzoyl) ethyl group, 2- (3-chlorobenzoyl) ethyl group, 2- (4-chlorobenzoyl) ethyl group, 2- (2-bromobenzoyl) ethyl group, 2- (3-bromobenzoyl) ethyl group , 2- (4-bromobenzoyl) ethyl group, 2- (2-trifluoromethylbenzoyl) ethyl group, 2- (3-trifluoromethylbenzoyl) ethyl group, 2- (4-trifluoromethylbenzoyl) ethyl group , 2- (2-trifluoromethoxybenzoyl) ethyl group, 2- (3-trifluoromethoxybenzoyl) ethyl group, -(4-trifluoromethoxybenzoyl) ethyl group, 3- (2-chlorobenzoyl) propyl group, 3- (3-chlorobenzoyl) propyl group, 3- (4-chlorobenzoyl) propyl group, 3- (2- (2-chlorobenzoyl) propyl group) Trifluoromethylbenzoyl) propyl group, 3- (3-trifluoromethylbenzoyl) propyl group, 3- (4-trifluoromethylbenzoyl) propyl group, 3- (2-trifluoromethoxybenzoyl) propyl group, 3- (3- (2-trifluoromethoxybenzoyl) propyl group 3-trifluoromethoxybenzoyl) propyl, 3- (4-trifluoromethoxybenzoyl) propyl, 4- (2-chlorobenzoyl) butyl, 4- (3-chlorobenzoyl) butyl, 4- (4-) Chlorobenzoyl) butyl group, 4- (2-trifluoromethylbenzoyl) butyl group, 4- (3-t) Fluoromethylbenzoyl) butyl group, 4- (4-trifluoromethylbenzoyl) butyl group, 4- (2-trifluoromethoxybenzoyl) butyl group, 4- (3-trifluoromethoxybenzoyl) butyl group, 4- (4 -Trifluoromethoxybenzoyl) butyl group, 5- (2-chlorobenzoyl) pentyl group, 5- (3-chlorobenzoyl) pentyl group, 5- (4-chlorobenzoyl) pentyl group, 5- (2-trifluoromethyl) Benzoyl) pentyl group, 5- (3-trifluoromethylbenzoyl) pentyl group, 5- (4-trifluoromethylbenzoyl) pentyl group, 5- (2-trifluoromethoxybenzoyl) pentyl group, 5- (3-trimethyl pentyl) group Fluoromethoxybenzoyl) pentyl group, 5- (4-trifluoromethoxybenzoyl) ) Pentyl group, 6- (2-chlorobenzoyl) hexyl group, 6- (3-chlorobenzoyl) hexyl group, 6- (4-chlorobenzoyl) hexyl group, 6- (2-trifluoromethylbenzoyl) hexyl group, 6- (3-trifluoromethylbenzoyl) hexyl group, 6- (4-trifluoromethylbenzoyl) hexyl group, 6- (2-trifluoromethoxybenzoyl) hexyl group, 6- (3-trifluoromethoxybenzoyl) hexyl Group, a benzoyl C1-6 alkyl group such as 6- (4-trifluoromethoxybenzoyl) hexyl group (on the phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1 1 to 5 groups, preferably 1 to 3 groups selected from the group consisting of -6 alkoxy groups Mention may be made of the conversion may be not).

A phenoxy group (on the phenyl ring, a halogen atom; a halogen substituted or unsubstituted C1-6 alkyl group; a halogen substituted or unsubstituted C1-6 alkoxy group; a C1-4 alkylenedioxy group; a C1-6 alkoxycarbonyl group Cyano group; C2-6 alkenyl group; nitro group; phenyl group; amino optionally having a group selected from the group consisting of phenyl group, C1-6 alkyl group, carbamoyl group and C1-6 alkanoyl group as a substituent Group: C1-6 alkanoyl substituted C1-6 alkyl group; hydroxyl group; C1-6 alkoxycarbonyl substituted C1-6 alkyl group; phenyl C1-6 alkyl group; C1-6 alkanoyl group; C1-6 alkylthio group; 4-triazolyl group; isoxazolyl group; imidazolyl group; benzothiazolyl group; 2H- Nzazotriazolyl group; pyrrolyl group; benzoxazolyl group; piperazinyl group [C.sub.1-6 alkoxycarbonyl group and phenyl C.sub.1-6 alkyl group as substituents (on halogen ring, halogen atom, halogen substitution or on phenyl ring; At least one group selected from the group consisting of an unsubstituted C.sub.1-6 alkyl group and a group selected from the group consisting of a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group) [1 type may be substituted]; piperidyl group [in the piperidine ring, at least one amino group may be substituted. On the amino group, a C 1-6 alkyl group as a substituent and phenyl as a substituent group Group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6. Or at least one group selected from the group consisting of lkoxy groups may be substituted), and a group consisting of a carbamoyl group As at least one kind of selected group may be substituted), for example, phenoxy group, 2-fluorophenoxy group, 3-fluorophenoxy group, 4-fluorophenoxy group, 2-chlorophenoxy group, 3- Chlorophenoxy group, 4-chlorophenoxy group, 2-bromophenoxy group, 3-bromophenoxy group, 4-bromophenoxy group, 2-iodophenoxy group, 3-iodophenoxy group, 4-iodophenoxy group, 2,3- Difluorophenoxy group, 3,4-difluorophenoxy group, 3,5-difluorophenoxy group, 2,4-difluorophenoxy Group, 2,6-difluorophenoxy group, 2,3-dichlorophenoxy group, 3,4-dichlorophenoxy group, 3,5-dichlorophenoxy group, 2,4-dichlorophenoxy group, 2,6-dichlorophenoxy group, 2,3,4-trifluorophenoxy group, 3,4,5-trifluorophenoxy group, 3,4,5-trichlorophenoxy group, 2,4,6-trifluorophenoxy group, 2,3,4,5 , 6-pentafluorophenoxy group, 2,4,6-trichlorophenoxy group, 2-fluoro-4-chlorophenoxy group, 2-fluoro-4-bromophenoxy group, 3-fluoro-4-chlorophenoxy group, 2- Methylphenoxy group, 3-methylphenoxy group, 4-methylphenoxy group, 2,6-dimethylphenoxy group, 2,4,6-trimethylphenol Group, 2-methyl-3-chlorophenoxy group, 3-methyl-4-chlorophenoxy group, 2-chloro-4-methylphenoxy group, 2-methyl-3-fluorophenoxy group, 2-trifluoromethylphenoxy group, 3-trifluoromethylphenoxy group, 4-trifluoromethylphenoxy group, 3,5-di (trifluoromethyl) phenoxy group, 3,4-di (trifluoromethyl) phenoxy group, 2,4-di (trifluoro) Methyl) phenoxy group, 2-pentafluoroethyl phenoxy group, 3-pentafluoroethyl phenoxy group, 4-pentafluoroethyl phenoxy group, 2-isopropyl phenoxy group, 3-isopropyl phenoxy group, 4-isopropyl phenoxy group, 2-tert -Butylphenoxy group, 3-tert-butylphenoxy 4-tert-butylphenoxy group, 2-sec-butylphenoxy group, 3-sec-butylphenoxy group, 4-sec-butylphenoxy group, 4-n-butylphenoxy group, 4-n-pentylphenoxy group, 4 -N-hexylphenoxy group, 2-n-heptafluoropropylphenoxy group, 3-n-heptafluoropropylphenoxy group, 4-n-heptafluoropropylphenoxy group, 4-pentylphenoxy group, 4-hexylphenoxy group, 2 -Methoxyphenoxy group, 3-methoxyphenoxy group, 4-methoxyphenoxy group, 2-methoxy-3-chlorophenoxy group, 2-fluoro-3-methoxyphenoxy group, 2-fluoro-4-methoxyphenoxy group, 2-fluoro -4-bromophenoxy and 2,4-dimethylphenoxy 2,3-Dimethylphenoxy, 3,5-dimethylphenoxy, 2,5-dimethylphenoxy, 4-isopropoxyphenoxy, 4-n-butoxyphenoxy, 2,4-dimethoxyphenoxy, 2, 3-dimethoxyphenoxy group, 3,5-dimethoxyphenoxy group, 2,5-dimethoxyphenoxy group, 2,4,6-trimethoxyphenoxy group, 3,5-ditrifluoromethoxyphenoxy group, 2-isopropoxyphenoxy group, 3-chloro-4-methoxyphenoxy group, 2-chloro-4-trifluoromethoxyphenoxy group, 3-methyl-4-fluorophenoxy group, 4-bromo-3-trifluoromethylphenoxy group, 2,6-dimethoxyphenoxy Group, 2-trifluoromethoxyphenoxy group, 3-trifluoromethoxy group Noxy group, 4-trifluoromethoxyphenoxy group, 2,3-di (trifluoromethoxy) phenoxy group, 3,5-di (trifluoromethoxy) phenoxy group, 2,4-di (trifluoromethoxy) phenoxy group, 2-pentafluoroethoxyphenoxy group, 3-pentafluoroethoxyphenoxy group, 4-pentafluoroethoxyphenoxy group, 3-isopropoxyphenoxy group, 2-tert-butoxyphenoxy group, 3-tert-butoxyphenoxy group, 4-tert -Butoxyphenoxy group, 2-sec-butoxyphenoxy group, 3-sec-butoxyphenoxy group, 4-sec-butoxyphenoxy group, 4-n-hexyloxyphenoxy group, 2-n-heptafluoropropoxyphenoxy group, 3- n-heptafluoropropo Siphenoxy, 4-n-heptafluoropropoxyphenoxy, 2,3-methylenedioxyphenoxy, 3,4-methylenedioxyphenoxy, 2,3-ethylenedioxyphenoxy, 3,4-ethylenedi Oxyphenoxy group, 2-methoxycarbonylphenoxy group, 3-methoxycarbonylphenoxy group, 4-methoxycarbonylphenoxy group, 2-ethoxycarbonylphenoxy group, 3-ethoxycarbonylphenoxy group, 4-ethoxycarbonylphenoxy group, 4-propoxycarbonyl group Phenoxy group, 4-butoxycarbonylphenoxy group, 4-pentoxy carbonylphenoxy group, 4-hexyloxycarbonylphenoxy group, 2-cyanophenoxy group, 3-cyanophenoxy group, 4-cyanophenoxy group, 2,3-di Cyanophenoxy group, 2,4,6-tricyanophenoxy group, 2-vinylphenoxy group, 3-vinylphenoxy group, 4-vinylphenoxy group, 2-allylphenoxy group, 3-allylphenoxy group, 4-allylphenoxy group , 2- (3-butenyl) phenoxy group, 3- (3-butenyl) phenoxy group, 4- (3-butenyl) phenoxy group, 2- (4-pentenyl) phenoxy group, 3- (4-pentenyl) phenoxy group , 4- (4-pentenyl) phenoxy group, 2- (5-hexenyl) phenoxy group, 3- (5-hexenyl) phenoxy group, 4- (5-hexenyl) phenoxy group, 2-nitrophenoxy group, 3-nitro Phenoxy group, 4-nitrophenoxy group, 2,3-dinitrophenoxy group, 2,4-dinitrophenoxy group, 2,4,6-tri Trophenoxy group, 2-biphenylyloxy group, 3-biphenylyloxy group, 4-biphenylyloxy group, 2-dimethylamino phenoxy group, 3-dimethylamino phenoxy group, 4-dimethylamino phenoxy group, 2-diethyl amino phenoxy Group, 3-diethylaminophenoxy group, 4-diethylaminophenoxy group, 2-di- (N-propyl) aminophenoxy group, 3-di- (N-propyl) aminophenoxy group, 4-di- (N-propyl) amino Phenoxy group, 2-diphenylaminophenoxy group, 3-diphenylaminophenoxy group, 4-diphenylaminophenoxy group, 2-acetylaminophenoxy group, 3-acetylaminophenoxy group, 4-acetylaminophenoxy group, 2-propionylaminophenoxy Group, 3-propi Nylaminophenoxy group, 4-propionylaminophenoxy group, 2-butyrylaminophenoxy group, 3-butyrylaminophenoxy group, 4-butyrylaminophenoxy group, 4-pentanoylaminophenoxy group, 4-hexanoylaminophenoxy Group, 3- (N-methyl-N-phenylamino) phenoxy group, 2- (N-acetyl-N-methylamino) phenoxy group, 2-carbamoylaminophenoxy group, 3-carbamoylaminophenoxy group, 4-carbamoylamino Phenoxy group, 4- (N-acetyl-N-phenylamino) phenoxy group, 4-acetylmethyl phenoxy group, 4-propionyl methyl phenoxy group, 4-n-butyrylmethyl phenoxy group, 4- (2-acetyl ethyl) Phenoxy group, 4- (3-acetylpropyl) Phenoxy group, 4- (4-acetylbutyl) phenoxy group, 4- (5-acetylpentyl) phenoxy group, 4- (6-acetylhexyl) phenoxy group, 2-hydroxyphenoxy group, 3-hydroxyphenoxy group, 4- Hydroxyphenoxy group, 2,4-dihydroxyphenoxy group, 2,4,6-trihydroxyphenoxy group, 2-hydroxy-3-chlorophenoxy group, 2-fluoro-3-hydroxyphenoxy group, 2-fluoro-4-hydroxy group Phenoxy group, 4-methoxycarbonylmethylphenoxy group, 4-ethoxycarbonylmethylphenoxy group, 4-n-propoxycarbonylmethylphenoxy group, 4- (2-ethoxycarbonylethyl) phenoxy group, 4- (3-ethoxycarbonylpropyl) Phenoxy group, 4- (4-d Xylcarbonylbutyl) phenoxy group, 4- (5-ethoxycarbonylpentyl) phenoxy group, 4- (6-ethoxycarbonylhexyl) phenoxy group, 2-benzylphenoxy group, 3-benzylphenoxy group, 4-benzylphenoxy group, 2 -(2-phenylethyl) phenoxy group, 3- (2-phenylethyl) phenoxy group, 4- (2-phenylethyl) phenoxy group, 2- (3-phenylpropyl) phenoxy group, 3- (3-phenylpropyl) ) Phenoxy group, 4- (3-phenylpropyl) phenoxy group, 2- (4-phenylbutyl) phenoxy group, 3- (4-phenylbutyl) phenoxy group, 4- (4-phenylbutyl) phenoxy group, 2- (5-phenylpentyl) phenoxy group, 3- (5-phenylpentyl) phenoxy , 4- (5-phenylpentyl) phenoxy, 2- (6-phenylhexyl) phenoxy, 3- (6-phenylhexyl) phenoxy, 4- (6-phenylhexyl) phenoxy, 2-acetylphenoxy , 3-acetylphenoxy group, 4-acetylphenoxy group, 4-n-propionylphenoxy group, 4-n-butyrylphenoxy group, 4-n-pentanoylphenoxy group, 4-n-hexanoylphenoxy group, 2 -Methylthiophenoxy group, 3-methylthiophenoxy group, 4-methylthiophenoxy group, 4-ethylthiophenoxy group, 4-n-propylthiophenoxy group, 4-isopropylthiophenoxy group, 4-n-butylthiophenoxy group, 4 -Tert-butylthiophenoxy group, 4-n-pentylthiophenoxy group, 4-n-hexylthiophenoxy group, 2,4-dimethylthiophenoxy group, 3,4,5-dimethylthiophenoxy group, 2- (1,2,4-triazol-1-yl) phenoxy group, 3- (3 1,2,4-Triazol-1-yl) phenoxy group, 4- (1,2,4-trido)


Azol-1-yl) phenoxy group, 2- (3-isoxazolyl) phenoxy group, 3- (4-isoxazolyl) phenoxy group, 4- (5-isoxazolyl) phenoxy group, 2- (1-imidazolyl) phenoxy group, 3 -(1-imidazolyl) phenoxy group, 4- (1-imidazolyl) phenoxy group, 2- (2-benzothiazolyl) phenoxy group, 3- (2-benzothiazolyl) phenoxy group, 4- (2-benzothiazolyl) phenoxy group, 2 -(2H-benzotriazol-2-yl) phenoxy group, 3- (2H-benzotriazol-2-yl) phenoxy group, 4- (2H-benzotriazol-2-yl) phenoxy group, 2- (1-pyrrolyl) ) Phenoxy group, 3- (1-pyrrolyl) phenoxy group, 4- (1-pyrrolyl) phenoxy , 2- (2-benzoxazolyl) phenoxy group, 3- (2-benzoxazolyl) phenoxy group, 4- (2-benzoxazolyl) phenoxy group, 2- (1-piperazinyl) phenoxy group, 3- (1-piperazinyl) phenoxy group, 4- (1-piperazinyl) phenoxy group, 4- (4-methoxycarbonyl-1-piperazinyl) phenoxy group, 4- (4-ethoxycarbonyl-1-piperazinyl) phenoxy group, 4- (4-n-propoxycarbonyl-1-piperazinyl) phenoxy group, 4- (4-n-butoxycarbonyl-1-piperazinyl) phenoxy group, 4- (4-n-pentyloxycarbonyl-1-piperazinyl) phenoxy Group, 4- (4-n-hexyloxycarbonyl-1-piperazinyl) phenoxy group, 4- (4-ben) Le-1-piperazinyl) phenoxy group, 4- (4- (2-phenethyl) -1-piperazinyl) phenoxy group, 4- (4- (3-phenylpropyl) -1-piperazinyl) phenoxy group, 4- (4 -(4-phenylbutyl) -1-piperazinyl) phenoxy group, 4- (4- (5-phenylpentyl) -1-piperazinyl) phenoxy group, 4- (4- (6-phenylhexyl) -1-piperazinyl) A phenoxy group, 4- [4- (2-fluorobenzyl) -1-piperazinyl] phenoxy group, 4- [4- (3-fluorobenzyl) -1-piperazinyl] phenoxy group, 4- [4- (4-fluoro) Benzyl) -1-piperazinyl] phenoxy group, 4- [4- (2-chlorobenzyl) -1-piperazinyl] phenoxy group, 4- [4- (3-chlorobenzyl) Le) -1-Piperazinyl] phenoxy group, 4- [4- (4-chlorobenzyl) -1-piperazinyl] phenoxy group, 4- [4- (2,3-dichlorobenzyl) -1-piperazinyl] phenoxy group, 4- [4- (2,4-dichlorobenzyl) -1-piperazinyl] phenoxy group, 4- [4- (3,4-dichlorobenzyl) -1-piperazinyl] phenoxy group, 4- [4- (3, 5-dichlorobenzyl) -1-piperazinyl] phenoxy group, 4- [4- (3,4,5-trichlorobenzyl) -1-piperazinyl] phenoxy group, 4- [4- (2-trifluoromethylbenzyl)- 1-piperazinyl] phenoxy group, 4- [4- (3-trifluoromethylbenzyl) -1-piperazinyl] phenoxy group, 4- [4- (4-trifluoromethylbenzyl) 4) 4-Piperazinyl] phenoxy group, 4- [4- (4-methylbenzyl) -1-piperazinyl] phenoxy group, 4- [4- (3,4-dimethylbenzyl) -1-piperazinyl] phenoxy group, 4 -[4- (2,4,6-trimethylbenzyl) -1-piperazinyl] phenoxy group, 4- [4- (2-pentafluoroethylbenzyl) -1-piperazinyl] phenoxy group, 4- [4- (3) -Pentafluoroethylbenzyl) -1-piperazinyl] phenoxy group, 4- [4- (4-pentafluoroethylbenzyl) -1-piperazinyl] phenoxy group, 4- [4- (2-trifluoromethoxybenzyl) -1 -Piperazinyl] phenoxy group, 4- [4- (3-trifluoromethoxybenzyl) -1-piperazinyl] phenoxy group, 4- [4- (4- -Trifluoromethoxybenzyl) -1-piperazinyl] phenoxy group, 4- [4- (4-methoxybenzyl) -1-piperazinyl] phenoxy group, 4- [4- (3,4-dimethoxybenzyl) -1-piperazinyl Phenoxy group, 4- [4- (2,4,6-trimethoxybenzyl) -1-piperazinyl] phenoxy group, 4- [4- (2-pentafluoroethoxybenzyl) -1-piperazinyl] phenoxy group, 4 -[4- (3-Pentafluoroethoxybenzyl) -1-piperazinyl] phenoxy group, 4- [4- (4-pentafluoroethoxybenzyl) -1-piperazinyl] phenoxy group, 4- {4- [2- (2- (2-pentafluoroethoxybenzyl)] 4-trifluoromethoxyphenyl) ethyl] -1-piperazinyl} phenoxy group, 4- {4- [3- (4-trifluorometh) Xyphenyl) propyl] -1-piperazinyl} phenoxy group, 4- {4- [4- (4-trifluoromethoxyphenyl) butyl] -1-piperazinyl} phenoxy group, 4- {4- [5- (4-tri-butyl] phenoxy group] Fluoromethoxyphenyl) pentyl] -1-piperazinyl} phenoxy group, 4- {4- [6- (4-trifluoromethoxyphenyl) hexyl] -1-piperazinyl} phenoxy group, 4- {4- [2- (4) -Trifluoromethylphenyl) ethyl] -1-piperazinyl} phenoxy group, 4- {4- [3- (4-trifluoromethylphenyl) propyl] -1-piperazinyl} phenoxy group, 4- {4- [4-] (4-Trifluoromethylphenyl) butyl] -1-piperazinyl} phenoxy group, 4- {4- [5- (4-trifluoromethylpheny] Pentyl) -1-piperazinyl} phenoxy group, 4- {4- [6- (4-trifluoromethylphenyl) hexyl] -1-piperazinyl} phenoxy group, 2-piperidinophenoxy group, 3-piperidine Nophenoxy group, 4-piperidinophenoxy group, 2- (4-amino-1-piperidyl) phenoxy group, 3- (4-amino-1-piperidyl) phenoxy group, 4- (4-amino-1-piperidyl) ) Phenoxy group, 4- (4-methylamino-1-piperidyl) phenoxy group, 4- (4-ethylamino-1-piperidyl) phenoxy group, 4- (4-n-propylamino-1-piperidyl) phenoxy group 4- (4-dimethylamino-1-piperidyl) phenoxy group, 4- (4-diethylamino-1-piperidyl) phenoxy group, 4- (4-di-) -Propylamino-1-piperidyl) phenoxy group, 4- (4-phenylamino-1-piperidyl) phenoxy group, 4- [4- (N-phenyl-N-methylamino) -1-piperidyl] phenoxy group, 4 -[4- (2-fluorophenylamino) -1-piperidyl] phenoxy group, 4- [4- (3-fluorophenylamino) -1-piperidyl] phenoxy group, 4- [4- (4-fluorophenylamino) )-1-Piperidyl] phenoxy group, 4- [4- (2-chlorophenylamino) -1-piperidyl] phenoxy group, 4- [4- (3-chlorophenylamino) -1-piperidyl] phenoxy group, 4- [4 4- (4-chlorophenylamino) -1-piperidyl] phenoxy group, 4- [4- (2,3-dichlorophenylamino) -1-piperidyl Phenoxy group, 4- [4- (2,4-dichlorophenylamino) -1-piperidyl] phenoxy group, 4- [4- (3,4-dichlorophenylamino) -1-piperidyl] phenoxy group, 4- [4 -(3,5-dichlorophenylamino) -1-piperidyl] phenoxy group, 4- [4- (2-trifluoromethylphenylamino) -1-piperidyl] phenoxy group, 4- [4- (2-methylphenylamino] ) -Piperidyl] phenoxy group, 4- [4- (2,3-dimethylphenylamino) -1-piperidyl] phenoxy group, 4- [4- (2-trifluoromethylphenylamino) -1-piperidyl] Phenoxy group, 4- [4- (2,4,6-trimethylphenylamino) -1-piperidyl] phenoxy group, 4- [4- (4-trifluoromethane) Rulphenylamino) -1-piperidyl] phenoxy group, 4- [4- (2-pentafluoroethylphenylamino) -1-piperidyl] phenoxy group, 4- [4- (3-pentafluoroethylphenylamino) -1 -Piperidyl] phenoxy group, 4- [4- (4-pentafluoroethylphenylamino) -1-piperidyl] phenoxy group, 4- [4- (2-trifluoromethoxyphenylamino) -1-piperidyl] phenoxy group, 4- [4- (2-methoxyphenylamino) -1-piperidyl] phenoxy group, 4- [4- (2,3-dimethoxyphenylamino) -1-piperidyl] phenoxy group, 4- [4- (2, 4,6-Trimethoxyphenylamino) -1-piperidyl] phenoxy group, 4- {4- [N-methyl-N- (2,4,6-to] Methoxyphenylamino)]-1-piperidyl} phenoxy group, 4- {4- [N-methyl-N- (3,4-dimethylphenylamino)]-1-piperidyl} phenoxy group, 4- [4- ( 3-trifluoromethoxyphenylamino) -1-piperidyl] phenoxy group, 4- [4- (4-trifluoromethoxyphenylamino) -1-piperidyl] phenoxy group, 4- [4- (2-pentafluoroethoxyphenyl) Amino) -1-piperidyl] phenoxy group, 4- [4- (3-pentafluoroethoxyphenylamino) -1-piperidyl] phenoxy group, 4- [4- (4-pentafluoroethoxyphenylamino) -1-piperidyl Phenoxy group, 2-carbamoyl phenoxy group, 3-carbamoyl phenoxy group, 4-carbamoyl phenoxy And the like (a phenyl atom on a phenyl ring; a halogen substituted or unsubstituted C1-6 alkyl group; a halogen substituted or unsubstituted C1-6 alkoxy group; a C1 to 4 alkylenedioxy group; C1 to C4) 6 alkoxycarbonyl group; cyano group; C2-6 alkenyl group; nitro group; phenyl group; 1 group selected from the group consisting of phenyl group, C1-6 alkyl group, carbamoyl group and C1-6 alkanoyl group as a substituent C1-6 alkanoyl substituted C1-6 alkyl group; hydroxyl group; C1-6 alkoxycarbonyl substituted C1-6 alkyl group; phenyl C1-6 alkyl group; C1-6 alkanoyl group; 6 alkylthio groups; 1,2,4 triazolyl groups; isoxazolyl groups; imidazolyl groups; benzothia Ryl group; 2H-benzotriazolyl group; pyrrolyl group; benzoxazolyl group; piperazinyl group [C.sub.1-6 alkoxycarbonyl group and phenyl C.sub.1-6 alkyl group as substituents on the piperazine ring (on the phenyl ring (on the phenyl ring Is substituted by 1 to 5, preferably 1 to 3 groups selected from the group consisting of halogen atoms, halogen-substituted or unsubstituted C.sub.1-6 alkyl groups and halogen-substituted or unsubstituted C.sub.1-6 alkoxy groups; It may be A group selected from the group consisting of 1 to 3 groups may be substituted); piperidyl group [an amino group as a substituent on the piperidine ring (C 1 to 6 alkyl as a substituent on the amino group Group and phenyl group (1 to 5 groups selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group on the phenyl ring) And preferably 1 to 3 groups may be substituted), and 1 to 3 groups selected from the group consisting of may be substituted] and groups selected from the group consisting of carbamoyl groups may be 1 to 5 And preferably 1 to 3 substituents may be mentioned.

  Phenyl group (on the phenyl ring, a phenoxy group as a substituent [on the phenyl ring, a halogen atom as a substituent, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group At least one of a group selected from the group consisting of: a group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group As at least one of the selected groups may be substituted), for example, phenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3- Chlorophenyl group, 4-chlorophenyl group, 2-bromophenyl group, 3-bromophenyl group, 4-bromophenyl group, 2-iodophenyl Group, 3-iodophenyl group, 4-iodophenyl group, 2,3-difluorophenyl group, 3,4-difluorophenyl group, 3,5-difluorophenyl group, 2,4-difluorophenyl group, 2, 6 -Difluorophenyl group, 2,3-dichlorophenyl group, 3,4-dichlorophenyl group, 3,5-dichlorophenyl group, 2,4-dichlorophenyl group, 2,6-dichlorophenyl group, 2,3,4-trifluorophenyl group 2,4,5-trifluorophenyl group, 3,4,5-trichlorophenyl group, 2,4,6-trifluorophenyl group, 2,3,4,5,6-pentafluorophenyl group, 2, 4,6-Trichlorophenyl group, 2-fluoro-4-chlorophenyl group, 2-fluoro-4-bromophenyl group, 3-fluoro-4-chlorophenyl group Group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 2-methyl-3-chlorophenyl group, 3-methyl-4-chlorophenyl group, 2-chloro-4-methylphenyl group, 2 -Methyl-3-fluorophenyl group, 2-trifluoromethylphenyl group, 3-trifluoromethylphenyl group, 4-trifluoromethylphenyl group, 2-pentafluoroethylphenyl group, 3-pentafluoroethylphenyl group, 4 -Pentafluoroethylphenyl group, 2-isopropylphenyl group, 3-isopropylphenyl group, 4-isopropylphenyl group, 2-tert-butylphenyl group, 3-tert-butylphenyl group, 4-tert-butylphenyl group, 2 -Sec-butylphenyl group, 3-sec-butylphenyl group, 4-s ec-butylphenyl group, 2-n-heptafluoropropylphenyl group, 3-n-heptafluoropropylphenyl group, 4-n-heptafluoropropylphenyl group, 4-pentylphenyl group, 4-hexylphenyl group, 2- Fluoro-4-bromophenyl group, 4-chloro-3-fluorophenyl group, 2,3,4-trichlorophenyl group, 4-n-butylphenyl group, 2,4-dimethylphenyl group, 2,3-dimethylphenyl group Group, 2,4-dimethylphenyl group, 2,6-dimethylphenyl group, 3,5-dimethylphenyl group, 2,5-dimethylphenyl group, 2,4,6-trimethylphenyl group, 3,5-ditrifluoro Methylphenyl group, 4-n-butoxyphenyl group, 2,4-dimethoxyphenyl group, 2,3-dimethoxyphenyl group, 2, 6 Dimethoxyphenyl group, 3,5-dimethoxyphenyl group, 2,5-dimethoxyphenyl group, 3,5-ditrifluoromethoxyphenyl group, 2,4,6-trimethoxyphenyl group, 3-chloro-4-methoxyphenyl group , 2-chloro-4-trifluoromethoxyphenyl group, 3-methyl-4-fluorophenyl group, 4-bromo-3-trifluoromethylphenyl group, 2-methoxyphenyl group, 3-methoxyphenyl group, 4-methoxy Phenyl group, 2-methoxy-3-chlorophenyl group, 2-fluoro-3-methoxyphenyl group, 2-fluoro-4-methoxyphenyl group, 2,6-dimethoxyphenyl group, 2-trifluoromethoxyphenyl group, 3- Trifluoromethoxyphenyl group, 4-trifluoromethoxyphenyl group, 2-pentafluoro Ethoxyphenyl group, 3-pentafluoroethoxyphenyl group, 4-pentafluoroethoxyphenyl group, 2-isopropoxyphenyl group, 3-isopropoxyphenyl group, 4-isopropoxyphenyl group, 2-tert-butoxyphenyl group, 3 3-tert-butoxyphenyl group, 4-tert-butoxyphenyl group, 2-sec-butoxyphenyl group, 3-sec-butoxyphenyl group, 4-sec-butoxyphenyl group, 2-n-heptafluoropropoxyphenyl group, 3 -N-heptafluoropropoxyphenyl group, 4-n-heptafluoropropoxyphenyl group, 4-pentyloxyphenyl group, 4-hexyloxyphenyl group, 2-phenoxyphenyl group, 3-phenoxyphenyl group, 4-phenoxyphenyl group , 2- (2-) Rolophenoxy) phenyl group, 2- (3-chlorophenoxy) phenyl group, 2- (4-chlorophenoxy) phenyl group, 3- (2-chlorophenoxy) phenyl group, 3- (3-chlorophenoxy) phenyl group, 3- (4-chlorophenoxy) phenyl group, 4- (2-chlorophenoxy) phenyl group, 4- (3-chlorophenoxy) phenyl group, 4- (4-chlorophenoxy) phenyl group, 2- (2-trichlorophenoxy) phenyl group Fluoromethylphenoxy) phenyl group, 2- (2-methylphenoxy) phenyl group, 2- (3-trifluoromethylphenoxy) phenyl group, 2- (4-trifluoromethylphenoxy) phenyl group, 3- (2- Trifluoromethylphenoxy) phenyl group, 3- (3-trifluoromethylphenoxy) phenyl group, 3- (4-trif Omethylphenoxy) phenyl group, 4- (2-trifluoromethylphenoxy) phenyl group, 4- (3-trifluoromethylphenoxy) phenyl group, 4- (4-trifluoromethylphenoxy) phenyl group, 2- (2 -Trifluoromethoxyphenoxy) phenyl group, 2- (3-trifluoromethoxyphenoxy) phenyl group, 2- (4-trifluoromethoxyphenoxy) phenyl group, 2- (4-methoxyphenoxy) phenyl group, 2- (2 2,4-dimethylphenoxy) phenyl group 2- (2,4,6-trimethylphenoxy) phenyl group 2- (3,4-dimethoxyphenoxy) phenyl group 2- (3,4,5-trimethoxyphenoxy) Phenyl group, 3- (2-trifluoromethoxyphenoxy) phenyl group, 3- (3-trif Oromethoxyphenoxy) phenyl group, 3- (4-trifluoromethoxyphenoxy) phenyl group, 4- (2-trifluoromethoxyphenoxy) phenyl group, 4- (3-trifluoromethoxyphenoxy) phenyl group, 4- (4 Phenyl group such as trifluoromethoxyphenoxy) phenyl group (a phenyl group as a substituent, a phenoxy group as a substituent [a phenyl atom as a substituent, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen as a substituent Group types selected from the group consisting of substituted or unsubstituted C1-6 alkoxy groups may be substituted with 1 to 5, preferably 1 to 3 groups; halogen atoms, halogen substituted or unsubstituted C1 1 to 5 groups selected from the group consisting of 6 alkyl groups and halogen substituted or unsubstituted C1-6 alkoxy groups are preferable Or 1 to 3 may be substituted).

  The C3-8 cycloalkyl-C1-6 alkoxy group is a group composed of a cyclic alkyl group having 3 to 8 carbon atoms and an alkoxy group having 1 to 6 carbon atoms, and examples thereof include a cyclopropyl methoxy group, 2-cyclopropylethoxy group, 3-cyclopropylpropoxy group, 4-cyclopropylbutoxy group, 5-cyclopropylpentyloxy group, 6-cyclopropylhexyloxy group, cyclobutyl methoxy group, 2-cyclobutyl ethoxy group, 3 -Cyclobutylpropoxy, 4-cyclobutylbutoxy, 5-cyclobutylpentyloxy, 6-cyclobutylhexyloxy, cyclopentylmethoxy, 2-cyclopentylethoxy, 3-cyclopentylpropoxy, 4-cyclopentylbutoxy , 5-cyclopentylpentyloxy group 6-Cyclopentylhexyloxy group, cyclohexylmethoxy group, 2-cyclohexylethoxy group, 3-cyclohexylpropoxy group, 4-cyclohexylbutoxy group, 5-cyclohexylpentyloxy group, 6-cyclohexylhexyloxy group, cycloheptylmethoxy group, 2- Cycloheptylethoxy group, 3-cycloheptylpropoxy group, 4-cycloheptylbutoxy group, 5-cycloheptylpentyloxy group, 6-cycloheptylhexyloxy group, cyclooctyl methoxy group, 2-cyclooctyl ethoxy group, 3-cyclo The octyl propoxy group, 4-cyclo octyl butoxy group, 5- cyclo octyl pentyloxy group, 6- cyclo octylhexyl oxy group etc. can be mentioned.

  A phenylcarbamoyl group (in which at least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group is substituted on a phenyl ring And “optionally substituted” means a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group on the phenyl ring. 5 groups, preferably 1 to 3 anilines, which may be substituted aniline, N-C1-6 alkyl aniline or N-phenyl C1-6 alkyl aniline and a carbonyl group, for example, a phenylcarbamoyl group , 2-fluorophenylcarbamoyl group, 3-fluorophenylcarbamoyl group, 4-fluorophenylcarbamoyl group Group, 2-chlorophenylcarbamoyl group, 3-chlorophenylcarbamoyl group, 4-chlorophenylcarbamoyl group, 2-bromophenylcarbamoyl group, 3-bromophenylcarbamoyl group, 4-bromophenylcarbamoyl group, 2-iodophenylcarbamoyl group, 3- Iodophenylcarbamoyl group, 4-iodophenylcarbamoyl group, 2,3-difluorophenylcarbamoyl group, 3,4-difluorophenylcarbamoyl group, 3,5-difluorophenylcarbamoyl group, 2,4-difluorophenylcarbamoyl group, 2, 6-difluorophenylcarbamoyl group, 2,3-dichlorophenylcarbamoyl group, 3,4-dichlorophenylcarbamoyl group, 3,5-dichlorophenylcarbamoyl group, 2,4-dichlorophenyl Ruvamoyl group, 2,6-dichlorophenylcarbamoyl group, 3,4,5-trifluorophenylcarbamoyl group, 2,3,4,5,6-pentafluorophenylcarbamoyl group, 3,4,5-trichlorophenylcarbamoyl group, 2,4,6-trifluorophenylcarbamoyl group, 2,4,6-trichlorophenylcarbamoyl group, 2-methylphenylcarbamoyl group, 3-methylphenylcarbamoyl group, 4-methylphenylcarbamoyl group, 2-methyl-3- Chlorophenylcarbamoyl group, 3-methyl-4-chlorophenylcarbamoyl group, 2-chloro-4-methylphenylcarbamoyl group, 2-methyl-3-fluorophenylcarbamoyl group, 2-trifluoromethylphenylcarbamoyl group, 3-trifluoromethyl Phenylca Rubamoyl group, N-methyl-N-phenylcarbamoyl group, N- (2-fluorophenyl) -N-methylcarbamoyl group, N- (3-fluorophenyl) -N-methylcarbamoyl group, N- (4-fluorophenyl) ) -N-methylcarbamoyl group, N- (2-chlorophenyl) -N-methylcarbamoyl group, N- (3-chlorophenyl) -N-methylcarbamoyl group, N- (4-chlorophenyl) -N-methylcarbamoyl group, N- (4-bromophenyl) -N-methylcarbamoyl group, N- (2-iodophenyl) -N-methylcarbamoyl group, N- (3-iodophenyl) -N-methylcarbamoyl group, N- (4-iodophenyl) Iodophenyl) -N-methylcarbamoyl group, N- (2,3-difluorophenyl) -N-methylcarbamoyl group, N- 3,4-Difluorophenyl) -N-methylcarbamoyl group, N- (3,5-difluorophenyl) -N-methylcarbamoyl group, N- (2,4-difluorophenyl) -N-methylcarbamoyl group, N- (2,6-difluorophenyl) -N-methylcarbamoyl group, N- (2,3-dichlorophenyl) -N-methylcarbamoyl group, N- (3,4-dichlorophenyl) -N-methylcarbamoyl group, n- ( 3,5-Dichlorophenyl) -N-methylcarbamoyl group, N- (2,4-dichlorophenyl) -N-methylcarbamoyl group, N- (2,6-dichlorophenyl) -N-methylcarbamoyl group, N- (3, 4,5-Trifluorophenyl) -N-methylcarbamoyl group, N- (3,4,5-trichlorophenyl) -N-methylcarbyl Moyl group, N- (2,4,6-trifluorophenyl) -N-methylcarbamoyl group, N- (2,4,6-trichlorophenyl) -N-methylcarbamoyl group, N- (2-methylphenyl) -N-methylcarbamoyl group, N- (3-methylphenyl) -N-methylcarbamoyl group, N- (4-methylphenyl) -N-methylcarbamoyl group, N- (2-methyl-3-chlorophenyl) -N -Methylcarbamoyl group, N- (3-methyl-4-chlorophenyl) -N-methylcarbamoyl group, N- (2-chloro-4-methylphenyl) -N-methylcarbamoyl group, N- (2-methyl-3) -Fluorophenyl) -N-methylcarbamoyl group, N- (2-trifluoromethylphenyl) -N-methylcarbamoyl group, N- (4-trifluoromethyl) Phenyl) -N-methylcarbamoyl group, N-benzyl-N-phenylcarbamoyl group, N-benzyl-N- (2-fluorophenyl) carbamoyl group, N-benzyl-N- (3-fluorophenyl) carbamoyl group, N -Benzyl-N- (4-fluorophenyl) carbamoyl group, N-benzyl-N- (2-chlorophenyl) carbamoyl group, N-benzyl-N- (3-chlorophenyl) carbamoyl group, N-benzyl-N- (4 -Chlorophenyl) carbamoyl group, N-benzyl-N- (2-bromophenyl) carbamoyl group, N-benzyl-N- (3-bromophenyl) carbamoyl group, N-benzyl-N- (4-bromophenyl) carbamoyl group , N-benzyl-N- (2-iodophenyl) carbamoyl group, N-benzyl-N- ( -Iodophenyl) carbamoyl group, N-benzyl-N- (4-iodophenyl) carbamoyl group, N-benzyl-N- (2,3-difluorophenyl) carbamoyl group, N-benzyl-N- (3,4-) Difluorophenyl) carbamoyl group, N-benzyl-N- (3,5-difluorophenyl) carbamoyl group, N-benzyl-N- (2,4-difluorophenyl) carbamoyl group, N-benzyl-N- (2,6 -Difluorophenyl) carbamoyl group, n-benzyl-N- (2,3-dichlorophenyl) carbamoyl group, N-benzyl-N- (3,4-dichlorophenyl) carbamoyl group, N-benzyl-N- (3,5-) Dichlorophenyl) carbamoyl group, N-benzyl-N- (2,4-dichlorophenyl) carbamoyl group, N-be Zyl-N- (2,6-dichlorophenyl) carbamoyl group, N-benzyl-N- (3,4,5-trifluorophenyl) carbamoyl group, N-benzyl-N- (3,4,5-trichlorophenyl) Carbamoyl group, N-benzyl-N- (2,4,6-trifluorophenyl) carbamoyl group, N-benzyl-N- (2,4,6-trichlorophenyl) carbamoyl group, N-benzyl-N- (2 -Methylphenyl) carbamoyl group, N-benzyl-N- (3-methylphenyl) carbamoyl group, N-benzyl-N- (4-methylphenyl) carbamoyl group, N-benzyl-N- (2-methyl-3-) Chlorophenyl) carbamoyl group, N-benzyl-N- (3-methyl-4-chlorophenyl) carbamoyl group, n-benzyl-N- (2-chloro- 4-Methylphenyl) carbamoyl group, N-benzyl-N- (2-methyl-3-fluorophenyl) carbamoyl group, N-benzyl-N- (2-trifluoromethylphenyl) carbamoyl group, N-benzyl-N- (3-trifluoromethylphenyl) carbamoyl group, N-benzyl-N- (4-trifluoromethylphenyl) carbamoyl group, 2-pentafluoroethylphenylcarbamoyl group, 3-pentafluoroethylphenylcarbamoyl group, 4-pentafluoro Ethylphenylcarbamoyl group, 2-isopropylphenylcarbamoyl group, 3-isopropylphenylcarbamoyl group, 4-isopropylphenylcarbamoyl group, 2-tert-butylphenylcarbamoyl group, 3-tert-butylphenylcarbamoyl group, 4- ert-butylphenylcarbamoyl group, 2-sec-butylphenylcarbamoyl group, 3-sec-butylphenylcarbamoyl group, 4-sec-butylphenylcarbamoyl group, 2-n-heptafluoropropylphenylcarbamoyl group, 3-n-hepta Fluoropropylphenylcarbamoyl group, 4-n-heptafluoropropylphenylcarbamoyl group, 4-pentylphenylcarbamoyl group, 4-hexylphenylcarbamoyl group, 2,4-dimethylphenylcarbamoyl group, 2,4,6-trimethylphenylcarbamoyl group , 3,4-dimethoxyphenylcarbamoyl group, 3,4,5-trimethoxyphenylcarbamoyl group, 2-methoxyphenylcarbamoyl group, 3-methoxyphenylcarbamoyl group, 4-methoxypheny Carbamoyl group, 2-methoxy-3-chlorophenylcarbamoyl group, 2-fluoro-3-methoxyphenylcarbamoyl group, 2-fluoro-4-methoxyphenylcarbamoyl group, 2,6-dimethoxyphenylcarbamoyl group, 2,3,4- Trifluorophenylcarbamoyl group, 3,4,5-trifluorophenylcarbamoyl group, 2-trifluoromethoxyphenylcarbamoyl group, 3-trifluoromethoxyphenylcarbamoyl group, 4-trifluoromethoxyphenylcarbamoyl group, 2-pentafluoroethoxy Phenylcarbamoyl group, 3-pentafluoroethoxyphenylcarbamoyl group, 4-pentafluoroethoxyphenylcarbamoyl group, 2-isopropoxyphenylcarbamoyl group, 3-isopropoxyphenyl group Ruvamoyl group, 4-isopropoxyphenylcarbamoyl group, 2-tert-butoxyphenylcarbamoyl group, 3-tert-butoxyphenylcarbamoyl group, 4-tert-butoxyphenylcarbamoyl group, 2-sec-butoxyphenylcarbamoyl group, 3-sec 4-butoxyphenylcarbamoyl group, 4-sec-butoxyphenylcarbamoyl group, 2-n-heptafluoropropoxyphenylcarbamoyl group, 3-n-heptafluoropropoxyphenylcarbamoyl group, 4-n-heptafluoropropoxyphenylcarbamoyl group, 4- Examples include n-pentyloxyphenylcarbamoyl group, 4-n-hexyloxyphenylcarbamoyl group and the like.

  As the naphthyloxy group (on the naphthalene ring, at least one C1-6 alkyl group may be substituted), for example, 1-naphthyloxy group, 2-naphthyloxy group, 2-methyl-1 -Naphthyloxy group, 3-methyl-1-naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-1-naphthyloxy group, 6-methyl-1-naphthyloxy group, 7-methyl-1 -Naphthyloxy group, 8-methyl-1-naphthyloxy group, 1-methyl-2-naphthyloxy group, 5-methyl-2-naphthyloxy group, 4-ethyl-1-naphthyloxy group, 5-ethyl-1 -Naphthyloxy group, 6-ethyl-1-naphthyloxy group, 1-ethyl-2-naphthyloxy group, 5-ethyl-2-naphthyloxy group, 5-n-propyl-1-naphthylo group And 6-n-propyl-1-naphthyloxy, 1-n-propyl-2-naphthyloxy, 5-n-propyl-2-naphthyloxy and 5-n-butyl-1-naphthyloxy 6-n-butyl-1-naphthyloxy group, 1-n-butyl-2-naphthyloxy group, 5-n-butyl-2-naphthyloxy group, 5-n-pentyl-1-naphthyloxy group, 6 -N-pentyl-1-naphthyloxy group, 1-n-pentyl-2-naphthyloxy group, 5-n-pentyl-2-naphthyloxy group, 5-n-hexyl-1-naphthyloxy group, 6-n -Hexyl-1-naphthyloxy group, 1-n-hexyl-2-naphthyloxy group, 5-n-hexyl-2-naphthyloxy group, 2,4-dimethyl-1-naphthyloxy group, 4, 6, 7 -Trimethyl-2 (On the naphthalene ring, Cl to 6 alkyl groups may be 1-3 substituents as a substituent.) Naphthyloxy group such as naphthyloxy group and the like.

  2,3-Dihydrobenzofuryloxy group (On the 2,3-dihydrobenzofuran ring, at least one of a group selected from the group consisting of a C1-6 alkyl group and an oxo group may be substituted.) Are, for example, 2,3-dihydrobenzofuran-3-yloxy group, 2,3-dihydrobenzofuran-4-yloxy group, 2,3-dihydrobenzofuran-5-yloxy group, 2,3-dihydrobenzofuran-6- Yloxy group, 2,3-dihydrobenzofuran-7-yloxy group, 2-oxo-2,3-dihydrobenzofuran-3-yloxy group, 2-oxo-2,3-dihydrobenzofuran-4-yloxy group, 2-oxo -2,3-Dihydrobenzofuran-5-yloxy group, 2-oxo-2,3-dihydrobenzofuran-6-yloxy group 2-oxo-2,3-dihydrobenzofuran-7-yloxy group, 3-oxo-2,3-dihydrobenzofuran-2-yloxy group, 3-oxo-2,3-dihydrobenzofuran-4-yloxy group, 3- Oxo-2,3-dihydrobenzofuran-5-yloxy group, 3-oxo-2,3-dihydrobenzofuran-6-yloxy group, 3-oxo-2,3-dihydrobenzofuran-7-yloxy group, 2-methyl- 2,3-dihydrobenzofuran-3-yloxy group, 2-methyl-2,3-dihydrobenzofuran-4-yloxy group, 2-methyl-2,3-dihydrobenzofuran-5-yloxy group, 2-methyl-2, 3-dihydrobenzofuran-6-yloxy group, 2-methyl-2,3-dihydrobenzofuran-7-yloxy group, 2- Tyl-2,3-dihydrobenzofuran-3-yloxy group, 2-ethyl-2,3-dihydrobenzofuran-4-yloxy group, 2-ethyl-2,3-dihydrobenzofuran-5-yloxy group, 2-ethyl- 2,3-dihydrobenzofuran-6-yloxy group, 2-ethyl-2,3-dihydrobenzofuran-7-yloxy group, 4-methyl-2,3-dihydrobenzofuran-3-yloxy group, 5-methyl-2, 3-dihydrobenzofuran-4-yloxy group, 4-methyl-2,3-dihydrobenzofuran-5-yloxy group, 4-methyl-2,3-dihydrobenzofuran-6-yloxy group, 4-methyl-2,3- Dihydrobenzofuran-7-yloxy group, 5-methyl-2,3-dihydrobenzofuran-3-yloxy group, 4-methyl- 2,3-dihydrobenzofuran-6-yloxy group, 4-methyl-2,3-dihydrobenzofuran-7-yloxy group, 6-methyl-2,3-dihydrobenzofuran-3-yloxy group, 6-methyl-2, 3-dihydrobenzofuran-4-yloxy, 6-methyl-2,3-dihydrobenzofuran-5-yloxy, 6-methyl-2,3-dihydrobenzofuran-7-yloxy, 7-methyl-2,3- Dihydrobenzofuran-3-yloxy group, 7-methyl-2,3-dihydrobenzofuran-4-yloxy group, 7-methyl-2,3-dihydrobenzofuran-5-yloxy group, 7-methyl-2,3-dihydrobenzofuran group -6-yloxy group, 2-n-propyl-2,3-dihydrobenzofuran-5-yloxy group, 2-n-pro 2,3-dihydrobenzofuran-6-yloxy group, 2-n-butyl-2,3-dihydrobenzofuran-5-yloxy group, 2-n-butyl-2,3-dihydrobenzofuran-6-yloxy group, 2-n-pentyl-2,3-dihydrobenzofuran-5-yloxy group, 2-n-pentyl-2,3-dihydrobenzofuran-6-yloxy group, 2-n-hexyl-2,3-dihydrobenzofuran-5 -Yloxy group, 2-n-hexyl-2,3-dihydrobenzofuran-6-yloxy group, 2,2-dimethyl-2,3-dihydrobenzofuran-5-yloxy group, 2,2,4-trimethyl-2, 3-dihydrobenzofuran-5-yloxy group, 3-oxo-4-methyl-2,3-dihydrobenzofuran-5-yloxy group, 2,2-diphenyl A 2,3-dihydrobenzofuryloxy group such as a ethyl 3-oxo-2,3-dihydrobenzofuran-5-yloxy group (on the 2,3-dihydrobenzofuran ring, a group consisting of a C1-6 alkyl group and an oxo group 1 to 3 selected groups may be substituted).

  Examples of the benzothiazolyloxy group (on the benzothiazole ring, at least one C1-6 alkyl group may be substituted) include, for example, 2-benzothiazolyloxy group, 4-benzothiazolyl group Roxy group, 5-benzothiazolyloxy group, 6-benzothiazolyloxy group, 7-benzothiazolyloxy group, 2-methyl-5-benzothiazolyloxy group, 4-methyl-5- Benzothiazolyloxy group, 6-methyl-5-benzothiazolyloxy group, 7-methyl-5-benzothiazolyloxy group, 4-ethyl-2-benzothiazolyloxy group, 5-ethyl- 2-benzothiazolyloxy group, 6-ethyl-4-benzothiazolyloxy group, 7-ethyl-6-benzothiazolyloxy group, 4-n-propyl-7-benzothiazolyloxy group, 5-n Propyl-2-benzothiazolyloxy group, 6-n-propyl-2-benzothiazolyloxy group, 7-n-propyl-5-benzothiazolyloxy group, 4-n-butyl-5-benzo Thiazolyloxy group, 5-n-butyl-2-benzothiazolyloxy group, 6-n-butyl-2-benzothiazolyloxy group, 7-n-butyl-4-benzothiazolyloxy group , 4-n-pentyl-6-benzothiazolyloxy group, 5-n-pentyl-7-benzothiazolyloxy group, 6-n-pentyl-2-benzothiazolyloxy group, 7-n- Pentyl-2-benzothiazolyloxy group, 4-n-hexyl-2-benzothiazolyloxy group, 5-n-hexyl-2-benzothiazolyloxy group, 6-n-hexyl-2-benzo Thiazolyloxy group, 7-n- Benzothiazolyloxy group such as xyl-2-benzothiazolyloxy group, 2,4-dimethyl-5-benzothiazolyloxy group, 2,4,6-trimethyl-5-benzothiazolyloxy group (On the benzothiazole ring, 1 to 3 C1-6 alkyl groups may be substituted) can be mentioned.

  Examples of 1,2,3,4-tetrahydronaphthyloxy group (at least one oxo group may be substituted on the 1,2,3,4-tetrahydronaphthalene ring) include, for example, , 3,4-tetrahydro-1-naphthyloxy group, 1,2,3,4-tetrahydro-2-naphthyloxy group, 1,2,3,4-tetrahydro-6-naphthyloxy group, 1,2,3 , 4-tetrahydro-5-naphthyloxy group, 1,2,3,4-tetrahydro-1-oxo-5-naphthyloxy group, 1,2,3,4-tetrahydro-2-oxo-3-naphthyloxy group 1,2,3,4-tetrahydro-1-oxo-6-naphthyloxy, 1,2,3,4-tetrahydro-3-oxo-5-naphthyloxy, 1,2,3,4-tetrahydro -4-oxo-6 Naphthyloxy group, 1,2,3,4-tetrahydro-2-oxo-7-naphthyloxy group, and a 1,2,3,4-tetrahydro-1-oxo-8-naphthyloxy group or the like.

  Examples of the 1,3-benzooxathiolanyloxy group (at least one oxo group may be substituted on the 1,3-benzooxathiolane ring) include, for example, 1,3-benzooxathiothio. Lan-4-yloxy group, 1,3-benzooxathiolan-5-yloxy group, 1,3-benzooxathiolane-6-yloxy group, 1,3-benzooxathiolane-7-yloxy group, 2 -Oxo-1,3-benzooxathiolane-5-yloxy group, 2-oxo-1,3-benzooxathiolane-6-yloxy group, 2-oxo-1,3-benzooxathiolane-7- Examples include an yloxy group and the like.

  Examples of the isoquinolyloxy group include isoquinolin-1-yloxy group, isoquinolin-3-yloxy group, isoquinolin-4-yloxy group, isoquinolin-5-yloxy group, isoquinolin-6-yloxy group, isoquinolin-7-yloxy group. Group, isoquinolin-8-yloxy group and the like.

  The pyridyloxy group includes a 2-pyridyloxy group, a 3-pyridyloxy group, and a 4-pyridyloxy group.

  Examples of the quinolyloxy group (wherein at least one C1-6 alkyl group may be substituted on the quinoline ring) include, for example, 2-quinolyloxy group, 3-quinolyloxy group, 4-quinolyloxy group, 5-quinolyloxy group , 6-quinolyloxy group, 7-quinolyloxy group, 8-quinolyloxy group, 3-methyl-2-quinolyloxy group, 4-methyl-2-quinolyloxy group, 5-methyl-2-quinolyloxy group, 6-methyl-2-quinolyloxy group Group, 7-methyl-2-quinolyloxy group, 2-methyl-3-quinolyloxy group, 4-methyl-3-quinolyloxy group, 5-methyl-3-quinolyloxy group, 6-methyl-3-quinolyloxy group, 7-methyl -3-quinolyloxy group, 8-methyl-3-quinolyloxy group, 2-methyl-4-quinolyloxy Group, 3-methyl-4-quinolyloxy group, 5-methyl-4-quinolyloxy group, 6-methyl-4-quinolyloxy group, 7-methyl-4-quinolyloxy group, 8-methyl-4-quinolyloxy group, 2-methyl -5-quinolyloxy group, 4-methyl-5-quinolyloxy group, 3-methyl-5-quinolyloxy group, 6-methyl-5-quinolyloxy group, 7-methyl-5-quinolyloxy group, 8-methyl-5-quinolyloxy group , 2-methyl-6-quinolyloxy group, 4-methyl-6-quinolyloxy group, 5-methyl-6-quinolyloxy group, 3-methyl-6-quinolyloxy group, 7-methyl-6-quinolyloxy group, 8-methyl- 6-quinolyloxy group, 2-methyl-7-quinolyloxy group, 4-methyl-7-quinolyloxy group, 5-methyl-7 Quinolyloxy group, 6-methyl-7-quinolyloxy group, 3-methyl-7-quinolyloxy group, 8-methyl-7-quinolyloxy group, 2-methyl-8-quinolyloxy group, 4-methyl-8-quinolyloxy group, 5- Methyl-8-quinolyloxy group, 6-methyl-8-quinolyloxy group, 7-methyl-8-quinolyloxy group, 3-methyl-8-quinolyloxy group, 2,5-dimethyl-8-quinolyloxy group, 6,7-dimethyl -4-quinolyloxy group, 4,6,7-trimethyl-5-quinolyloxy group and methyl group of these compound groups to ethyl group, n-propyl group, n-butyl group, n-pentyl group or n-hexyl group (1 to 3 C1-6 alkyl groups may be substituted as a substituent on a quinolyloxy group such as a substituted compound group) Yes. Can be mentioned.

  The dibenzofuryloxy group is 1-dibenzofuryloxy group, 2-dibenzofuryloxy group, 3-dibenzofuryloxy group, 4-dibenzofuryloxy group, 5-dibenzofuryloxy group, 6-dibenzofuryloxy group, 7- It contains a dibenzofuryloxy group, an 8-dibenzofuryloxy group and a 9-dibenzofuryloxy group.

  As the 2H-chromenyloxy group (on the 2H-chromen ring, at least one oxo group may be substituted), for example, 4- (2H) chromenyloxy group, 5- (2H) chloro Menyloxy group, 6- (2H) chromenyloxy group, 7- (2H) chromenyloxy group, 8- (2H) chromenyloxy group, 2-oxo-4- (2H) chromenyloxy group, 2- Oxo-5- (2H) chromium nyloxy group, 2-oxo-6- (2H) chromium nyloxy group, 2-oxo-7- (2H) chromium nyloxy group, 2-oxo-8- (2H) chromium Menyloxy group etc. can be mentioned.

  Examples of the benzoisoxazolyloxy group include 3-benzoisoxazolyloxy group, 4-benzoisoxazolyloxy group, 5-benzoisoxazolyloxy group, 6-benzoisoxazolyloxy group Group, 7-benzoisoxazolyloxy group, etc. can be mentioned.

  Examples of the quinoxalyloxy group include a 2-quinoxalyloxy group, a 5-quinoxalyloxy group, and a 6-quinoxalyloxy group.

  As the 2,3-dihydro-1H-indenyloxy group (on the 2,3-dihydro-1H-indene ring, at least one oxo group may be substituted), for example, Dihydro-1H-inden-1-yloxy group, 2,3-dihydro-1H-inden-2-yloxy group, 2,3-dihydro-1H-inden-3-yloxy group, 2,3-dihydro-1H-indene -4-yloxy group, 2,3-dihydro-1H-inden-5-yloxy group, 2,3-dihydro-1H-inden-6-yloxy group, 2,3-dihydro-1H-inden-7-yloxy group 2,3-dihydro-1-oxo-1H-inden-2-yloxy group, 2,3-dihydro-1-oxo-1H-inden-3-yloxy group, 2,3-dihydro-1-oxo group S−1-1H-indene-4-yloxy group, 2,3-dihydro-1-oxo-1H-indene-5-yloxy group, 2,3-dihydro-1-oxo-1H-indene-6-yloxy group, 2 And 3-dihydro-1-oxo-1H-inden-7-yloxy group etc. can be mentioned.

  Examples of the benzofurazanyloxy group include 4-benzofurazanyloxy group, 5-benzofurazanyloxy group and the like.

  A phenyl C 2-6 alkenyl group (on the phenyl ring at least one of the groups selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group The term “optionally substituted” means that 1 to 5 groups, preferably 1 group selected from an unsubstituted or halogen atom, a halogen C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group are used. It is a group composed of an 基 3-substituted phenyl group and an alkenyl group having 2 to 6 carbon atoms and at least one double bond. The phenyl C2-6 alkenyl group includes both trans and cis forms. As such a phenyl C2-6 alkenyl group, in addition to the above-mentioned phenyl C2-6 alkenyl group, for example, 3- (2-fluorophenyl) -2-propenyl group, 3- (3-fluorophenyl) -2 -Propenyl group, 3- (4-fluorophenyl) -2-propenyl group, 3- (2,3-difluorophenyl) -2-propenyl group, 3- (2,3,4,5,6-pentafluorophenyl) ) -2-propenyl group, 3- (2,4-difluorophenyl) -2-propenyl group, 3- (3,4-difluorophenyl) -2-propenyl group, 3- (3,5-difluorophenyl)- 2-propenyl group, 3- (2-chlorophenyl) -2-propenyl group, 3- (3-chlorophenyl) -2-propenyl group, 3- (4-chlorophenyl) -2-propenyl group 3- (2,3-dichlorophenyl) -2-propenyl group, 3- (2,4-dichlorophenyl) -2-propenyl group, 3- (3,4-dichlorophenyl) -2-propenyl group, 3- (3) 5-dichlorophenyl) -2-propenyl group, 3- (2-bromophenyl) -2-propenyl group, 3- (3-bromophenyl) -2-propenyl group, 3- (4-bromophenyl) -2- Propenyl group, 3- (2-methylphenyl) -2-propenyl group, 3- (3-methylphenyl) -2-propenyl group, 3- (4-methylphenyl) -2-propenyl group, 3- (2- (2-methylphenyl) -2-propenyl group, 3- (2-methylphenyl) -2-propenyl group Trifluoromethylphenyl) -2-propenyl group, 3- (2-fluoro-4-bromophenyl) -2-propenyl group, 3- (4-chloro-3-fluorophenyl) -2-propenyl group, -(2,3,4-trichlorophenyl) -2-propenyl group, 3- (2,4,6-trichlorophenyl) -2-propenyl group, 3- (4-isopropylphenyl) -2-propenyl group, 3 -(4-n-butylphenyl) -2-propenyl group, 3- (2,4-dimethylphenyl) -2-propenyl group, 3- (2,3-dimethylphenyl) -2-propenyl group, 3- ( 2,6-dimethylphenyl) -2-propenyl group, 3- (3,5-dimethylphenyl) -2-propenyl group, 3- (2,5-dimethylphenyl) -2-propenyl group, 3- (2, 4,6-trimethylphenyl) -2-propenyl group, 3- (3,5-ditrifluoromethylphenyl) -2-propenyl group, 3- (4-n-butoxyphenyl) -2-propenyl group, 3- (3- 2,4-di Methoxyphenyl) -2-propenyl group, 3- (2,3-dimethoxyphenyl) -2-propenyl group, 3- (2,6-dimethoxyphenyl) -2-propenyl group, 3- (3,5-dimethoxyphenyl) ) -2-propenyl group, 3- (2,5-dimethoxyphenyl) -2-propenyl group, 3- (3,5-ditrifluoromethoxyphenyl) -2-propenyl group, 3- (3-chloro-4-) Methoxyphenyl) -2-propenyl group, 3- (2-chloro-4-trifluoromethoxyphenyl) -2-propenyl group, 3- (3-methyl-4-fluorophenyl) -2-propenyl group, 3- ( 4-bromo-3-trifluoromethylphenyl) -2-propenyl group, 3- (3-trifluoromethylphenyl) -2-propenyl group, 3- (4-trifluoromethyl) Phenyl) -2-propenyl group, 3- (2-trifluoromethoxyphenyl) -2-propenyl group, 3- (3-trifluoromethoxyphenyl) -2-propenyl group, 3- (4-trifluoromethoxyphenyl) -2-propenyl group, 3- (2-methoxyphenyl) -2-propenyl group, 3- (3-methoxyphenyl) -2-propenyl group, 3- (4-methoxyphenyl) -2-propenyl group, 3- (3,4-Dimethoxyphenyl) -2-propenyl group, 4- (4-chlorophenyl) -2-butenyl group, 4- (4-chlorophenyl) -3-butenyl group, 5- (4-chlorophenyl) -2- Pentenyl group, 5- (4-chlorophenyl) -4-pentenyl group, 5- (4-chlorophenyl) -3-pentenyl group, 6- (4-chlorophenyl) -5 Hexenyl, 6- (4-chlorophenyl) -4-hexenyl group, 6- (4-chlorophenyl) -3-hexenyl group, 6- (4-chlorophenyl) -3- can be exemplified hexenyl.

  As the C1-6 alkyl group (in the alkyl group, a morpholino group, a benzoyl group, a carbamoyl group optionally having a C1-6 alkyl group as a substituent, or a cyano group may be substituted), for example, a methyl group , Ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, morpholinomethyl group, 2-morpholinoethyl group, 3-morpholinopropyl group, 4-morpholinobutyl group, 5-morpholinopentyl Group, 6-morpholinohexyl group, benzoylmethyl group, 2-benzoylethyl group, 1-benzoylethyl group, 3-benzoylpropyl group, 4-benzoylbutyl group, 5-benzoylpentyl group, 6-benzoylhexyl group, carbamoylmethyl Group, 2-carbamoylethyl group, 1-carbamoylethyl group, 3-carbamoyl Ropyl group, 4-carbamoylbutyl group, 5-carbamoylpentyl group, 6-carbamoylhexyl group, 2-methyl-3-carbamoylpropyl group, 1,1-dimethyl-2-carbamoylethyl group, methylcarbamoylmethyl group, 2- Methylcarbamoylethyl group, 3-methylcarbamoylpropyl group, 4-methylcarbamoylbutyl group, 5-methylcarbamoylpentyl group, 6-methylcarbamoylhexyl group, dimethylcarbamoylmethyl group, 2-dimethylcarbamoylethyl group, 3-dimethylcarbamoylpropyl , 4-dimethylcarbamoylbutyl, 5-dimethylcarbamoylpentyl, 6-dimethylcarbamoylhexyl, diethylcarbamoylmethyl, 2-diethylcarbamoylethyl, 3-diethylcarbamoyl Ropyl, 4-diethylcarbamoylbutyl, 5-diethylcarbamoylpentyl, 6-diethylcarbamoylhexyl, n-propylcarbamoylmethyl, 2-n-propylcarbamoylethyl, 3-n-propylcarbamoylpropyl, -N-propylcarbamoylbutyl group, 5-n-propylcarbamoylpentyl group, 6-n-propylcarbamoylhexyl group, n-butylcarbamoylmethyl group, 2-n-butylcarbamoylethyl group, 3-n-butylcarbamoylpropyl group , 4-n-butylcarbamoylbutyl group, 5-n-butylcarbamoylpentyl group, 6-n-butylcarbamoylhexyl group, n-hexylcarbamoylmethyl group, 2-n-hexylcarbamoylethyl group, 3-n-hexylcarbamoyl group The Ropyl group, 4-n-hexylcarbamoylbutyl group, 5-n-hexylcarbamoylpentyl group, 6-n-hexylcarbamoylhexyl group, cyanomethyl group, 2-cyanoethyl group, 1-cyanoethyl group, 3-cyanopropyl group, 4 -Cyanobutyl group, 5-cyanopentyl group, 6-cyanohexyl group etc. can be mentioned.

  Phenyl C1-6 alkyl group (on the phenyl ring, halogen atom, cyano group, phenyl group, nitro group, C1-6 alkylthio group, C1-6 alkylsulfonyl group, phenyl C1-6 alkoxy group, C2-6 alkanoyloxy At least one group selected from the group consisting of a group, a halogen-substituted or unsubstituted C1-6 alkyl group, a halogen-substituted or unsubstituted C1-6 alkoxy group and a 1,2,3-thiadiazole group is substituted May be, for example, benzyl group, 1-phenethyl group, 2-phenethyl group, 3-phenylpropyl group, 2-phenylpropyl group, 4-phenylbutyl group, 5-phenylpentyl group, 4-phenylpentyl group Group, 6-phenylhexyl group, 4-biphenylylmethyl group, 2- (4-biphenylyl) ethyl group, 3 (4-biphenylyl) propyl group, 2- (4-biphenylyl) propyl group, 4- (4-biphenylyl) butyl group, 5- (4-biphenylyl) pentyl group, 4- (4-biphenylyl) pentyl group, 6- (4-biphenylyl) hexyl group, 2-fluorobenzyl group, 3-fluorobenzyl group, 4-fluorobenzyl group, 2-chlorobenzyl group, 3-chlorobenzyl group, 4-chlorobenzyl group, 2-bromobenzyl group, 3-bromobenzyl group, 4-bromobenzyl group, 2-iodobenzyl group, 3-iodobenzyl group, 4-iodobenzyl group, 2,3-difluorobenzyl group, 3,4-difluorobenzyl group, 3,5- Difluorobenzyl group, 2,4-difluorobenzyl group, 2,6-difluorobenzyl group, 2,4,6-trifluorobenzyl group 3,4,5-Trifluorobenzyl group, 2,3-dichlorobenzyl group, 3,4-dichlorobenzyl group, 3,5-dichlorobenzyl group, 2,4-dichlorobenzyl group, 2,6-dichlorobenzyl group 2,4,6-trichlorobenzyl group, 3,4,5-trichlorobenzyl group, 2-difluoromethyl benzyl group, 3-difluoromethyl benzyl group, 4-difluoromethyl benzyl group, 4-chloro-3-difluoromethyl group Benzyl, 3-chloro-4-difluoromethylbenzyl, 3-bromo-4-difluoromethylbenzyl, 3,5-difluoro-4-difluoromethylbenzyl, 2-fluoro-4-bromobenzyl, 4- Chloro-3-fluorobenzyl group, 2,3,4-trichlorobenzyl group, 4-isopropylbenzyl group, 4-n- Butyl benzyl group, 4-methylbenzyl group, 2-methylbenzyl group, 3-methylbenzyl group, 2,4-dimethylbenzyl group, 2,3-dimethylbenzyl group, 2,6-dimethylbenzyl group, 3,5- Dimethylbenzyl group, 2,5-dimethylbenzyl group, 2,4,6-trimethylbenzyl group, 3,5-ditrifluoromethylbenzyl group, 4-isopropoxybenzyl group, 4-n-butoxybenzyl group, 4-methoxy Benzyl group, 2-methoxybenzyl group, 3-methoxybenzyl group, 2,4-dimethoxybenzyl group, 2,3-dimethoxybenzyl group, 2,6-dimethoxybenzyl group, 3,5-dimethoxybenzyl group, 2,5 -Dimethoxybenzyl group, 2,4,6-trimethoxybenzyl group, 3,5-ditrifluoromethoxybenzyl group, 2,3,4 5,6-pentafluorobenzyl group, 2-isopropoxybenzyl group, 3-chloro-4-methoxybenzyl group, 2-chloro-4-trifluoromethoxybenzyl group, 3-methyl-4-fluorobenzyl group, 4- Bromo-3-trifluoromethylbenzyl group, 2-trifluoromethylbenzyl group, 3-trifluoromethylbenzyl group, 4-trifluoromethylbenzyl group, 4-fluoro-3-trifluoromethylbenzyl group, 3-fluoro- 4-trifluoromethylbenzyl group, 4-chloro-3-pentafluoroethyl benzyl group, 3-chloro-4-pentafluoroethyl benzyl group, 2-pentafluoroethyl benzyl group, 3-pentafluoroethyl benzyl group, 4- Pentafluoroethyl benzyl group, 2-trifluoromethoxy benzyl , 3-trifluoromethoxybenzyl group, 4-trifluoromethoxybenzyl group, 4-fluoro-3-trifluoromethoxybenzyl group, 3-fluoro-4-trifluoromethoxybenzyl group, 2-pentafluoroethoxybenzyl group, 3 -Pentafluoroethoxybenzyl group, 4-pentafluoroethoxybenzyl group, 3-chloro-4-trifluoromethoxybenzyl group, 3-chloro-4-pentafluoroethoxybenzyl group, 2- (2-trifluoromethylphenyl) ethyl Group, 2- (3-trifluoromethylphenyl) ethyl group, 2- (4-trifluoromethylphenyl) ethyl group, 2- (2-trifluoromethoxyphenyl) ethyl group, 2- (3-trifluoromethoxyphenyl) ) Ethyl group, 2- (4-trifluoromethoxyphenyl) Ethyl group, 2- (2-pentafluoroethoxyphenyl) ethyl group, 2- (3-pentafluoroethoxyphenyl) ethyl group, 2- (4-pentafluoroethoxyphenyl) ethyl group, 3- (2-trifluoromethyl) Phenyl) propyl group, 3- (3-trifluoromethylphenyl) propyl group, 3- (4-trifluoromethylphenyl) propyl group, 3- (2-trifluoromethoxyphenyl) propyl group, 3- (3- (3-trifluoromethylphenyl) propyl group Trifluoromethoxyphenyl) propyl group, 3- (4-trifluoromethoxyphenyl) propyl group, 3- (3-pentafluoroethoxyphenyl) propyl group, 3- (4-pentafluoroethoxyphenyl) propyl group, 4- (4- (4-pentafluoroethoxyphenyl) propyl group) 3-pentafluoroethoxyphenyl) butyl group, 5- (4-trifluoromethyl) Pentyl), 4- (4-trifluoromethylphenyl) pentyl, 4- (4-trifluoromethoxyphenyl) pentyl, 6- (3-trifluoromethylphenyl) hexyl, 6- (4-trimethyl) Fluoromethylphenyl) hexyl group, 6- (4-trifluoromethoxyphenyl) hexyl group, 2-methylthiobenzyl group, 3-methylthiobenzyl group, 4-methylthiobenzyl group, 2,3-dimethylthiobenzyl group, 2,4 , 6-trimethylthiobenzyl group, 2- (2-methylthiophenyl) ethyl group, 2- (3-methylthiophenyl) ethyl group, 2- (4-methylthiophenyl) ethyl group, 3- (4-methylthiophenyl) propyl Group, 4- (4-methylthiophenyl) butyl group, 5- (4-methylthiophenyl) pentyl group, 6 -(4-Methylthiophenyl) hexyl group, 2-benzyloxybenzyl group, 3-benzyloxybenzyl group, 4-benzyloxybenzyl group, 2- (2-benzyloxyphenyl) ethyl group, 2- (3-benzyloxy group Phenyl) ethyl group, 2- (4-benzyloxyphenyl) ethyl group, 3- (4-benzyloxyphenyl) propyl group, 4- (4-benzyloxyphenyl) butyl group, 5- (4-benzyloxyphenyl) Pentyl group, 6- (4-benzyloxyphenyl) hexyl group, 2- (2-phenylethoxy) benzyl group, 3- (2-phenylethoxy) benzyl group, 4- (2-phenylethoxy) benzyl group, 2- (2- (2-phenylethoxy) phenyl) ethyl group, 2- (3- (2-phenylethoxy) phenyl) ethyl Group, 2- (4- (2-phenylethoxy) phenyl) ethyl group, 3- (4- (2-phenylethoxy) phenyl) propyl group, 4- (4- (2-phenylethoxy) phenyl) butyl group, 5- (4- (2-phenylethoxy) phenyl) pentyl group, 6- (4- (2-phenylethoxy) phenyl) hexyl group, 2- (3-phenylpropoxy) benzyl group, 3- (3-phenylpropoxy) ) Benzyl group, 4- (3-phenylpropoxy) benzyl group, 2- (4-phenylbutoxy) benzyl group, 3- (4-phenylbutoxy) benzyl group, 4- (4-phenylbutoxy) benzyl group, 2- Acetyloxybenzyl group, 3-acetyloxybenzyl group, 4-acetyloxybenzyl group, 2- (2-acetyloxyphenyl) ethyl group, 2- 3-acetyloxyphenyl) ethyl group, 2- (4-acetyloxyphenyl) ethyl group, 3- (4-acetyloxyphenyl) propyl group, 4- (4-acetyloxyphenyl) butyl group, 5- (4- (4-acetyloxyphenyl) butyl group) Acetyloxyphenyl) pentyl group, 6- (4-acetyloxyphenyl) hexyl group, 2-methanesulfonylbenzyl group, 3-methanesulfonylbenzyl group, 4-methanesulfonylbenzyl group, 3,4-dimethanesulfonylbenzyl group, 3,4,5-trimethanesulfonylbenzyl group, 2- (2-methanesulfonylphenyl) ethyl group, 2- (3-methanesulfonylphenyl) ethyl group, 2- (4-methanesulfonylphenyl) ethyl group, 3- (4-methanesulfonylphenyl) propyl group, 4- (4-methanesulfonylphenyl) bu Ethyl, 5- (4-methanesulfonylphenyl) pentyl, 6- (4-methanesulfonylphenyl) hexyl, 2-cyanobenzyl, 3-cyanobenzyl, 4-cyanobenzyl, 2,4-dicyano Benzyl group, 3,4,5-tricyanobenzyl group, 2- (2-cyanophenyl) ethyl group, 2- (3-cyanophenyl) ethyl group, 2- (4-cyanophenyl) ethyl group, 3- ( 4-cyanophenyl) propyl group, 4- (4-cyanophenyl) butyl group, 5- (4-cyanophenyl) pentyl group, 6- (4-cyanophenyl) hexyl group, 2-nitrobenzyl group, 3-nitro Benzyl group, 4-nitrobenzyl group, 2,6-dinitrobenzyl group, 3,4,5-trinitrobenzyl group, 2- (2-nitrophenyl) ethyl group, 2- (3-) Rophenyl) ethyl group, 2- (4-nitrophenyl) ethyl group, 3- (4-nitrophenyl) propyl group, 4- (4-nitrophenyl) butyl group, 5- (4-nitrophenyl) pentyl group, 6 -(4-nitrophenyl) hexyl group, 2- (1,2,3-thiadiazol-4-yl) benzyl group, 3- (1,2,3-thiadiazol-4-yl) benzyl group, Phenyl C1-6 alkyl group such as 4- (1,2,3-thiadiazo-l-4-yl) benzyl group (on the phenyl ring, halogen atom, cyano group, phenyl group, nitro group, C1-6 alkylthio) Group, C1-6 alkylsulfonyl group, phenyl C1-6 alkoxy group, C2-6 alkanoyloxy group, halogen substituted or unsubstituted C1-6 alkyl group, halogen substituted or unsubstituted C1 1-5 from selected groups 6 alkoxy group and the group consisting of 1,2,3-thiadiazole group can be preferably exemplified may) also be 1-3 substituents.

  As a C 2 to C 6 alkenyl group, for example, a vinyl group, 2-propenyl group, 3-butenyl group, 2-butenyl group, 4-pentenyl group, 3-pentenyl group, 5-hexenyl group, 4-hexenyl group, 3-Hexenyl group etc. can be mentioned.

  Phenyl group (wherein at least one group selected from the group consisting of a halogen atom, a cyano group, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group on a phenyl ring is substituted For example, unsubstituted phenyl group, a halogen atom as defined above, a cyano group, a halogen substituted or unsubstituted C.sub.1-6 alkyl group, and a halogen substituted or unsubstituted C.sub.1-6 alkoxy. A phenyl group having 1 to 5, preferably 1 to 3 substituents selected from the group consisting of: more specifically, for example, a phenyl group, a 2-fluorophenyl group, a 3-fluorophenyl group , 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 2-bromophenyl group, -Bromophenyl group, 4-bromophenyl group, 2-iodophenyl group, 3-iodophenyl group, 4-iodophenyl group, 2,3-difluorophenyl group, 3,4-difluorophenyl group, 3,5-difluoro Phenyl group, 2,4-difluorophenyl group, 2,3,4,5,6-pentafluorophenyl group, 2,6-difluorophenyl group, 2,3-dichlorophenyl group, 3,4-dichlorophenyl group, 3, 5-dichlorophenyl group, 2,4-dichlorophenyl group, 2,6-dichlorophenyl group, 3,4,5-trifluorophenyl group, 3,4,5-trichlorophenyl group, 2,4,6-trifluorophenyl group 2,4,6-trichlorophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2-methyl-3 Chlorophenyl group, 3-methyl-4-chlorophenyl group, 2-chloro-4-methylphenyl group, 2-methyl-3-fluorophenyl group, 2-trifluoromethylphenyl group, 3-trifluoromethylphenyl group, 4- Trifluoromethylphenyl group, 2-pentafluoroethylphenyl group, 3-pentafluoroethylphenyl group, 4-pentafluoroethylphenyl group, 2-isopropylphenyl group, 3-isopropylphenyl group, 4-isopropylphenyl group, 2- tert-butylphenyl group, 3-tert-butylphenyl group, 4-tert-butylphenyl group, 2-sec-butylphenyl group, 3-sec-butylphenyl group, 4-sec-butylphenyl group, 2-n- Heptafluoropropylphenyl group, 3-n-heptafluoro Propylphenyl group, 4-n-heptafluoropropylphenyl group, 4-pentylphenyl group, 4-hexylphenyl group, 2-methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 3-chloro-2- Methoxyphenyl group, 2-fluoro-3-methoxyphenyl group, 2-fluoro-4-methoxyphenyl group, 2,6-dimethoxyphenyl group, 2,3,4-trifluorophenyl group, 2-fluoro-4-bromo group Phenyl group, 4-chloro-3-fluorophenyl group, 2,3,4-trichlorophenyl group, 4-n-butylphenyl group, 2,4-dimethylphenyl group, 2,3-dimethylphenyl group, 2, 6 -Dimethylphenyl group, 3,5-dimethylphenyl group, 2,5-dimethylphenyl group, 2,4,6-trimethylphenyl group, , 4,6-Trimethoxyphenyl group, 3,5-ditrifluoromethylphenyl group, 4-n-butoxyphenyl group, 2,4-dimethoxyphenyl group, 2,3-dimethoxyphenyl group, 3,5-dimethoxyphenyl group Group, 2,5-dimethoxyphenyl group, 3,5-ditrifluoromethoxyphenyl group, 3-chloro-4-methoxyphenyl group, 2-chloro-4-trifluoromethoxyphenyl group, 3-methyl-4-fluorophenyl group Group, 4-bromo-3-trifluoromethylphenyl group, 2-cyanophenyl group, 3-cyanophenyl group, 4-cyanophenyl group, 2-trifluoromethoxyphenyl group, 3-trifluoromethoxyphenyl group, 4- Trifluoromethoxyphenyl group, 3-fluoro-2-trifluoromethoxyphenyl group, 2-fluo -3-Trifluoromethoxyphenyl group, 3-fluoro-4-trifluoromethoxyphenyl group, 3-chloro-2-trifluoromethoxyphenyl group, 2-chloro-3-trifluoromethoxyphenyl group, 3-chloro-4 -Trifluoromethoxyphenyl group, 2-pentafluoroethoxyphenyl group, 3-pentafluoroethoxyphenyl group, 4-pentafluoroethoxyphenyl group, 3-chloro-2-pentafluoroethoxyphenyl group, 2-chloro-3-pentacene group Fluoroethoxyphenyl group, 3-chloro-4-pentafluoroethoxyphenyl group, 2-isopropoxyphenyl group, 3-isopropoxyphenyl group, 4-isopropoxyphenyl group, 2-tert-butoxyphenyl group, 3-tert- Butoxyphenyl group, 4-tert 4-butoxyphenyl group, 2-sec-butoxyphenyl group, 3-sec-butoxyphenyl group, 4-sec-butoxyphenyl group, 2-n-heptafluoropropoxyphenyl group, 3-n-heptafluoropropoxyphenyl group, 4 And -n-heptafluoropropoxyphenyl group, 4-n-pentoxyphenyl group, 4-n-hexyloxyphenyl group and the like can be mentioned.

  At least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group, and a halogen-substituted or unsubstituted C1-6 alkoxy group on the phenyl ring; As 1 type may be substituted, for example, phenylacetyl group, 3-phenylpropionyl group, 4-phenylbutyryl group, 5-phenylpentanoyl group, 6-phenylhexanoyl group, 4-fluorophenyl Acetyl group, 3- (4-fluorophenyl) propionyl group, 4- (4-fluorophenyl) butyryl group, 5- (4-fluorophenyl) pentanoyl group, 6- (4-fluorophenyl) hexanoyl group, 2-chlorophenyl Acetyl, 2,3,4,5,6-pentafluorophenylacetyl, 3- (3 -Chlorophenyl) propionyl group, 4- (2-chlorophenyl) butyryl group, 5- (2-chlorophenyl) pentanoyl group, 6- (2-chlorophenyl) hexanoyl group, 3-chlorophenylacetyl group, 3- (3-chlorophenyl) propionyl Group, 4- (3-chlorophenylphenyl) butyryl group, 5- (3-chlorophenyl) pentanoyl group, 6- (3-chlorophenyl) hexanoyl group, 4-chlorophenylacetyl group, 3- (4-chlorophenyl) propionyl group, 4 -(4-chlorophenyl) butyryl group, 5- (4-chlorophenyl) pentanoyl group, 6- (4-chlorophenyl) hexanoyl group, 3,4-dichlorophenylacetyl group, 3- (3,4-dichlorophenyl) propionyl group, 4 -(3,4-dichloropheny ) Butyryl group, 5- (3,4-dichlorophenyl) pentanoyl group, 6- (3,4-dichlorophenyl) hexanoyl group, 2-methylphenylacetyl group, 3-methylphenylacetyl group, 4-methylphenylacetyl group, 2,4,6-trimethylphenyl) acetyl group, (2,6-dimethoxyphenyl) acetyl group, (2,4,5-trimethoxyphenyl) acetyl group, (3,5-ditrifluoromethylphenyl) acetyl group, (3,5-ditrifluoromethoxyphenyl) acetyl group, 2-trifluoromethylphenylacetyl group, 3-trifluoromethylphenylacetyl group, 4-trifluoromethylphenylacetyl group, 2-phenylpropionyl group, 3- (2 -Methylphenyl) propionyl group, 3- (3-methylphenyl) group Lopionyl group, 3- (4-methylphenyl) propionyl group, 3- (2-trifluoromethylphenyl) propionyl group, 3- (3-trifluoromethylphenyl) propionyl group, 3- (4-trifluoromethylphenyl) group Propionyl group, 3- (3,5-dimethylphenyl) propionyl group, 4- (4-trifluoromethylphenyl) butyryl group, 5- (4-trifluoromethylphenyl) pentanoyl group, 6- (4-trifluoromethyl) Phenyl) hexanoyl group, 4- (4-pentafluoroethylphenyl) butyryl group, 5- (4-pentafluoroethylphenyl) pentanoyl group, 6- (4-pentafluoroethylphenyl) hexanoyl group, 2-methoxyphenylacetyl group , 3-methoxyphenylacetyl group, 4-methoxy group Group, 2-trifluoromethoxyphenylacetyl group, 3-trifluoromethoxyphenylacetyl group, 4-trifluoromethoxyphenylacetyl group, 3- (2-methoxyphenyl) propionyl group, 3- (3-methoxyphenyl) propionyl Group, 3- (4-methoxyphenyl) propionyl group, 3- (2-trifluoromethoxyphenyl) propionyl group, 3- (3-trifluoromethoxyphenyl) propionyl group, 3- (4-trifluoromethoxyphenyl) propionyl group Group, 3- (3,5-dimethoxyphenyl) propionyl group, 4- (4-trifluoromethoxyphenyl) butyryl group, 5- (4-trifluoromethoxyphenyl) pentanoyl group, 6- (4-trifluoromethoxyphenyl) group ) Hexanoyl group, 4 Phenyl C2-6 alkanoyl groups such as (4-trifluoromethoxyphenyl) butyryl group, 5- (4-pentafluoroethoxyphenyl) pentanoyl group, 6- (4-pentafluoroethoxyphenyl) hexanoyl group (on a phenyl ring) Is substituted by 1 to 5, preferably 1 to 3 groups selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group May be mentioned.

  A C1 to 20 alkoxycarbonyl group (on the alkoxy group, a halogen atom, an amino group which may have a C1 to 6 alkyl group as a substituent, and a C1 to 6 alkoxy substituted C1 to 6 alkoxy group And at least one kind of the group may be substituted) is selected from the group consisting of a halogen atom, an amino group which may have a C1-6 alkyl group as a substituent, and a C1-6 alkoxy substituted C1-6 alkoxy group A group having 1 to 20 carbon atoms which may have 1 to 7 carbon atoms, and an alkoxy group having 1 to 20 carbon atoms and a carbonyl group, and examples thereof include a methoxycarbonyl group, an ethoxycarbonyl group, and n-propoxy carbonyl Group, n-buXycarbonyl group, n-pentyloxycarbonyl group, n-hexyloxycarbonyl group, n-heptylo A carbonyl group, n-octyloxycarbonyl group, n-nonyloxycarbonyl group, n-decyloxycarbonyl group, n-undecyloxycarbonyl group, n-dodecyloxycarbonyl group, n-tridecyloxycarbonyl group, n- Tetradecyloxycarbonyl group, n-pentadecyloxycarbonyl group, n-hexadecyloxycarbonyl group, n-heptadecyloxycarbonyl group, n-octadecyloxycarbonyl group, n-nonadecyloxycarbonyl group, n-icosyloxy Carbonyl group, chloromethoxycarbonyl group, trichloromethoxycarbonyl group, 2-bromoethoxycarbonyl group, 2,2-dibromoethoxycarbonyl group, 3-fluoropropoxycarbonyl group, 4-iodobutoxyxoxycarbonyl group, 5, 5,4,4,3,3-heptafluoropentyloxycarbonyl group, 4,4,4,3,3,2,2-heptafluorobutoxycarbonyl group, 5-chloropentyloxycarbonyl group, 6-bromohexyl Oxycarbonyl group, 7-chloroheptyloxycarbonyl group, 8-iodooctyloxycarbonyl group, 9-chlorononyloxycarbonyl group, 10-bromodecyloxycarbonyl group, 11-fluoroundecyloxycarbonyl group, 12-iodododecyloxy Carbonyl group, 12-chlorododecyloxycarbonyl group, 13-fluorotridecyloxycarbonyl group, 14-bromotetradecyloxycarbonyl group, 15-iodopentadecyloxycarbonyl group, 16-chlorohexadecyloxycarbonyl group, 17-bromo Heptadecyloxycarbonyl group, 18-fluorooctadecyloxycarbonyl group, 19-chlorononadecyloxycarbonyl group, 20-chloroicosyloxycarbonyl group, aminomethoxycarbonyl group, diethylaminomethoxycarbonyl group, 2-diethylaminoethoxycarbonyl group, 3 -Diethylaminopropoxyoxycarbonyl group, 4-diethylaminobutoxycarbonyl group, 5-diethylaminopentyloxycarbonyl group, 6-diethylaminohexyloxycarbonyl group, 7-diethylaminoheptyloxycarbonyl group, 8-diethylaminobutyloxycarbonyl group, 9-diethylamino Nonyloxycarbonyl group, 10-diethylaminodecyloxycarbonyl group, 11-diethylaminodecyloxy carboni Group, 12-diethylaminododecyloxycarbonyl group, 13-diethylaminotridecyloxycarbonyl group, 14-diethylaminotetradecyloxycarbonyl group, 15-diethylaminopentadecyloxycarbonyl group, 16-diethylaminohexadecyloxycarbonyl group, 17-diethylaminohepta group Decyloxycarbonyl group, 18-diethylaminooctadecyloxycarbonyl group, 19-diethylaminononadecyloxycarbonyl group, 20-diethylamino icosyloxycarbonyl group, methoxyethoxymethoxycarbonyl group, 2- (2-ethoxyethoxy) ethoxycarbonyl group, 2 -(2-propoxyethoxy) ethoxycarbonyl group, 2- (2-butoxyethoxy) ethoxycarbonyl group, 2- (2-pen) Roxyethoxy) ethoxycarbonyl group, 2- (2-hexyloxyethoxy) ethoxycarbonyl group, 2-methoxyethoxyethoxycarbonyl group, 3- (3-methoxypropoxy) propoxycarbonyl group, 4- (4-methoxybutoxy) group Butoxycarbonyl group, 5- (5-methoxypentyloxy) pentyloxycarbonyl group, 6- (6-methoxyhexyloxy) hexyloxycarbonyl group, 7- (2-methoxyethoxy) heptyloxycarbonyl group, 8- (1 (one) -Methoxyethoxy) octyloxycarbonyl group, 9- (1-methoxyethoxy) nonyloxycarbonyl group, 10- (2-methoxyethoxy) decyloxycarbonyl group, 11- (1-methoxyethoxy) undecyloxycarbonyl group, 12 -(2- Toxethoxy) dodecyloxycarbonyl group, 12- (1-methoxyethoxy) dodecyloxycarbonyl group, 13- (2-methoxyethoxy) tridecyloxycarbonyl group, 14- (1-methoxyethoxy) tetradecyloxycarbonyl group, 15 -(2-methoxyethoxy) pentadecyloxycarbonyl group, 16- (1-methoxyethoxy) hexadecyloxycarbonyl group, 17- (2-methoxyethoxy) heptadecyloxycarbonyl group, 18- (1-methoxyethoxy) octadecyl An oxycarbonyl group, 19- (2-methoxyethoxy) nonadecyloxycarbonyl group, 20- (1-methoxyethoxy) icosyloxycarbonyl group, dimethylaminomethoxycarbonyl group, 2-methylaminoethoxycarbonyl group, 3- ( -Methyl-N-butylamino) propoxycarbonyl group, 4-propylaminobuoxycarbonyl group, 5-hexylaminopentyloxycarbonyl group, 6-pentylaminohexyloxycarbonyl group, 7- (N-ethyl-N-propyl group Amino) heptyloxycarbonyl group, 8- (N-propyl-N-hexyl) aminooctyloxycarbonyl group, 9- (N-pentyl-N-methylamino) nonyloxycarbonyl group, 10-dipropylaminodecyloxycarbonyl group 11-dipentylaminoundecyloxycarbonyl group, 12-dihexylaminododecyloxycarbonyl group, 12-dibutylaminododecyloxycarbonyl group, 13- (N-ethyl-N-butylamino) tridecyloxycarbonyl group, 14- (14 N- Methyl-N-hexylamino) tetradecyloxycarbonyl group, 15-dimethylaminopentadecyloxycarbonyl group, 16-dimethylaminohexadecyloxycarbonyl group, 17-dimethylaminoheptadecyloxycarbonyl group, 18-dimethylaminooctadecyloxycarbonyl Groups, 19-dimethylaminononadecyloxycarbonyl group, 20-dimethylaminoicosyloxycarbonyl group and the like.

Phenyl C1-6 alkoxycarbonyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group, a halogen substituted or unsubstituted C1-6 alkoxy group, a nitro group, a halogen substituted or unsubstituted Of a group selected from the group consisting of a C1-6 alkylthio group, an amino group which may have a C1-6 alkanoyl group, a phenyl C1-6 alkoxy group, a C1-6 alkoxycarbonyl group and a 1,2,3-thiadiazolyl group As at least one group may be substituted, for example, benzyloxycarbonyloxycarbonyl group, 1-phenethyloxycarbonyl group, 2-phenethyloxycarbonyl group, 3-phenylpropoxycarbonyl group, 2-phenylpropoxycarbonyl group , 4-phenylbutoxy carboni Group, 5-phenylpentyloxycarbonyl group, 4-phenylpentyloxycarbonyl group, 6-phenylhexyloxycarbonyl group, 2-fluorobenzyloxycarbonyl group, 3-fluorobenzyloxycarbonyl group, 4-fluorobenzyloxycarbonyl group, 2-chlorobenzyloxycarbonyl group, 3-chlorobenzyloxycarbonyl group, 4-chlorobenzyloxycarbonyl group, 2-bromobenzyloxycarbonyl group, 3-bromobenzyloxycarbonyl group, 4-bromobenzyloxycarbonyl group, 2- Iodobenzyloxycarbonyl group, 3-iodobenzyloxycarbonyl group, 4-iodobenzyloxycarbonyl group, 2,3-difluorobenzyloxycarbonyl group, 3,4-difluorobenzyloxy Rubonyl group, 3,5-difluorobenzyloxycarbonyl group, 2,4-difluorobenzyloxycarbonyl group, 2,6-difluorobenzyloxycarbonyl group, 2,4,6-trifluorobenzyloxycarbonyl group, 3,4, 5-trifluorobenzyloxycarbonyl group, 2,3-dichlorobenzyloxycarbonyl group, 3,4-dichlorobenzyloxycarbonyl group, 3,5-dichlorobenzyloxycarbonyl group, 2,4-dichlorobenzyloxycarbonyl group, 2 , 6-dichlorobenzyloxycarbonyl group, 2,4,6-trichlorobenzyloxycarbonyl group, 3,4,5-trichlorobenzyloxycarbonyl group, 2,3,4,5,6-pentafluorobenzyloxycarbonyl group, 2-difluoromethylbenzylo Xycarbonyl group, 3-difluoromethylbenzyloxycarbonyl group, 4-difluoromethylbenzyloxycarbonyl group, 4-chloro-3-difluoromethylbenzyloxycarbonyl group, 3-chloro-4-difluoromethylbenzyloxycarbonyl group, 3- Bromo-4-difluoromethylbenzyloxycarbonyl group, 3,5-difluoro-4-difluoromethylbenzyloxycarbonyl group, 2-trifluoromethylbenzyloxycarbonyl group, 2-fluoro-4-bromobenzyloxycarbonyl group, 4- Chloro-3-fluorobenzyloxycarbonyl group, 2,3,4-trichlorobenzyloxycarbonyl group, 4-isopropylbenzyloxycarbonyl group, 4-n-butylbenzyloxycarbonyl group, 4-methylbenzene Roxycarbonyl group, 2-methylbenzyloxycarbonyl group, 3-methylbenzyloxycarbonyl group, 2,4-dimethylbenzyloxycarbonyl group, 2,3-dimethylbenzyloxycarbonyl group, 2,6-dimethylbenzyloxycarbonyl group , 3,5-Dimethylbenzyloxycarbonyl group, 2,5-dimethylbenzyloxycarbonyl group, 2,4,6-trimethylbenzyloxycarbonyl group, 3,5-ditrifluoromethylbenzyloxycarbonyl group, 4-isopropoxybenzyl Oxycarbonyl group, 4-n-butoxybenzyloxycarbonyl group, 4-methoxybenzyloxycarbonyl group, 2-methoxybenzyloxycarbonyl group, 3-methoxybenzyloxycarbonyl group, 2,4-dimethoxybenzyloxy Carbonyl, 2,3-dimethoxybenzyloxycarbonyl, 2,6-dimethoxybenzyloxycarbonyl, 3,5-dimethoxybenzyloxycarbonyl, 2,5-dimethoxybenzyloxycarbonyl, 2,4,6-tri Methoxybenzyloxycarbonyl group, 3,5-ditrifluoromethoxybenzyloxycarbonyl group, 2-isopropoxybenzyloxycarbonyl group, 3-chloro-4-methoxybenzyloxycarbonyl group, 2-chloro-4-trifluoromethoxybenzyloxy Carbonyl group, 3-methyl-4-fluorobenzyloxycarbonyl group, 4-bromo-3-trifluoromethylbenzyloxycarbonyl group, 3-trifluoromethylbenzyloxycarbonyl group, 4-trifluoromethylbenzylo group Xycarbonyl group, 4-fluoro-3-trifluoromethylbenzyloxycarbonyl group, 3-fluoro-4-trifluoromethylbenzyloxycarbonyl group, 2-pentafluoroethylbenzyloxycarbonyl group, 4-chloro-3-pentafluoro group Ethyl benzyloxycarbonyl group, 3-chloro-4-pentafluoroethyl benzyloxycarbonyl group, 3-pentafluoroethyl benzyloxycarbonyl group, 4-pentafluoroethyl benzyloxycarbonyl group, 2-trifluoromethoxybenzyloxycarbonyl group, 3-trifluoromethoxybenzyloxycarbonyl group, 4-trifluoromethoxybenzyloxycarbonyl group, 4-fluoro-3-trifluoromethoxybenzyloxycarbonyl group, 3-fluoro- -Trifluoromethoxybenzyloxycarbonyl group, 2-pentafluoroethoxybenzyloxycarbonyl group, 3-pentafluoroethoxybenzyloxycarbonyl group, 4-pentafluoroethoxybenzyloxycarbonyl group, 3-chloro-4-trifluoromethoxybenzyloxy Carbonyl group, 3-chloro-4-pentafluoroethoxybenzyloxycarbonyl group, 2- (2-trifluoromethylphenyl) ethoxycarbonyl group, 2- (3-trifluoromethylphenyl) ethoxycarbonyl group, 2- (4- Trifluoromethylphenyl) ethoxycarbonyl group, (2-trifluoromethoxyphenyl) methoxycarbonyl group, (3-trifluoromethoxyphenyl) methoxycarbonyl group, 2- (4-trifluorometh Siphenyl) ethoxycarbonyl group, 2- (2-pentafluoroethoxyphenyl) ethoxycarbonyl group, 2- (3-pentafluoroethoxyphenyl) methoxycarbonyl group, 2- (4-pentafluoroethoxyphenyl) methoxycarbonyl group, 3- (2-trifluoromethylphenyl) propoxycarbonyl group, 3- (3-trifluoromethylphenyl) propoxycarbonyl group, 3- (4-trifluoromethylphenyl) propoxycarbonyl group, 3- (2-trifluoromethoxyphenyl) Propoxycarbonyl group, 3- (3-trifluoromethoxyphenyl) propoxycarbonyl group, 3- (4-trifluoromethoxyphenyl) propoxycarbonyl group, 3- (3-pentafluoroethoxyphenyl) propoxycarbonyl group Group, 3- (4-pentafluoroethoxyphenyl) propoxycarbonyl group, 4- (3-pentafluoroethoxyphenyl) butoxycarbonyl group, 5- (4-trifluoromethylphenyl) pentyloxycarbonyl group, 4- (4- Trifluoromethylphenyl) pentyloxycarbonyl group, 4- (4-trifluoromethoxyphenyl) pentyloxycarbonyl group, 6- (3-trifluoromethylphenyl) hexyloxycarbonyl group, 6- (4-trifluoromethylphenyl) group Hexyloxycarbonyl group, 6- (4-trifluoromethoxyphenyl) hexyloxycarbonyl group, 2-methylthiobenzyloxycarbonyl group, 3-methylthiobenzyloxycarbonyl group, 4-methylthiobenzyloxycarbonyl group, 2- ( -Methylthiophenyl) ethoxycarbonyl group, 2- (3-methylthiophenyl) ethoxycarbonyl group, 2- (4-methylthiophenyl) ethoxycarbonyl group, 3- (4-methylthiophenyl) propoxycarbonyl group, 4- (4-methylthio) Phenyl) butoxycarbonyl group, 5- (4-methylthiophenyl) pentyloxycarbonyl group, 6- (4-methylthiophenyl) hexyloxycarbonyl group, 2-trifluoromethylthiobenzyloxycarbonyl group, 3-trifluoromethylthiobenzyloxycarbonyl Group, 4-trifluoromethylthiobenzyloxycarbonyl group, 2- (2-trifluoromethylthiophenyl) ethoxycarbonyl group, 2- (3-trifluoromethylthiophenyl) ethoxycarbonyl group, 2- 4-trifluoromethylthiophenyl) ethoxycarbonyl group, 3- (4-trifluoromethylthiophenyl) propoxycarbonyl group, 4- (4-trifluoromethylthiophenyl) butoxycarbonyl group, 5- (4-trifluoromethylthiophenyl) pentyl Oxycarbonyl group, 6- (4-trifluoromethylthiophenyl) hexyloxycarbonyl group, 2-benzyloxybenzyloxycarbonyl group, 3-benzyloxybenzyloxycarbonyl group, 4-benzyloxybenzyloxycarbonyl group, 2- (2 -Benzyloxyphenyl) methoxycarbonyl group, 2- (3-benzyloxyphenyl) methoxycarbonyl group, 2- (4-benzyloxyphenyl) methoxycarbonyl group, 3- (4-benzyloxyphenyl) group ) Propoxycarbonyl group, 4- (4-benzyloxyphenyl) butoxycarbonyl group, 5- (4-benzyloxyphenyl) pentyloxycarbonyl group, 6- (4-benzyloxyphenyl) hexyloxycarbonyl group, 2- (2 -Phenylethoxy) benzyloxycarbonyl group, 3- (2-phenylethoxy) benzyloxycarbonyl group, 4- (2-phenylethoxy) benzyloxycarbonyl group, 2- (2- (2-phenylethoxy) phenyl) ethoxycarbonyl Group, 2- (3- (2-phenylethoxy) phenyl) ethoxycarbonyl group, 2- (4- (2-phenylethoxy) phenyl) ethoxycarbonyl group, 3- (4- (2-phenylethoxy) phenyl) propoxy Carbonyl group, 4- (4- (2-phenyl ether) Xyl) phenyl) butoxycarbonyl group, 5- (4- (2-phenylethoxy) phenyl) pentyloxycarbonyl group, 6- (4- (2-phenylethoxy) phenyl) hexyloxycarbonyl group, 2- (3- phenyl group Propoxy) benzyloxycarbonyl group, 3- (3-phenylpropoxy) benzyloxycarbonyl group, 4- (3-phenylpropoxy) benzyloxycarbonyl group, 2- (4-phenylbutoxy) benzyloxycarbonyl group, 3- (4) -Phenylbutoxy) benzyloxycarbonyl group, 4- (4-phenylbutoxy) benzyloxycarbonyl group, 2-methoxycarbonylbenzyloxycarbonyl group, 3-methoxycarbonylbenzyloxycarbonyl group, 4-methoxycarbonylbenzyloxycar Group, 2- (2-methoxycarbonylphenyl) ethoxycarbonyl group, 2- (3-methoxycarbonylphenyl) ethoxycarbonyl group, 2- (4-methoxycarbonylphenyl) ethoxycarbonyl group, 3- (4-methoxycarbonylphenyl) group ) Propoxycarbonyl group, 4- (4-Methoxycarbonylphenyl) butoxycarbonyl group, 5- (4-methoxycarbonylphenyl) pentyloxycarbonyl group, 6- (4-methoxycarbonylphenyl) hexyloxycarbonyl group, 2-butyryl Aminobenzyloxycarbonyl group, 3-butyrylaminobenzyloxycarbonyl group, 4-butyrylaminobenzyloxycarbonyl group, 2- (2-butyrylaminophenyl) ethoxycarbonyl group, 2- (3-butyrylaminopheny E) ethoxycarbonyl group, 2- (4-butyrylaminophenyl) ethoxycarbonyl group, 3- (4-butyrylaminophenyl) propoxycarbonyl group, 4- (4-butyrylaminophenyl) butoxycarbonyl group, 5- (4-butyrylaminophenyl) pentylo


Xycarbonyl group, 6- (4-butyrylaminophenyl) hexyloxycarbonyl group, 2-nitrobenzyloxycarbonyl group, 3-nitrobenzyloxycarbonyl group, 4-nitrobenzyloxycarbonyl group, 2- (2-nitrophenyl group) 2.) Ethoxycarbonyl group, 2- (3-nitrophenyl) ethoxycarbonyl group, 2- (2,4-dinitrophenyl) ethoxycarbonyl group, 2- (2,4,6-trinitrophenyl) ethoxycarbonyl group, 2- (4-nitrophenyl) ethoxycarbonyl group, 3- (4-nitrophenyl) propoxycarbonyl group, 4- (4-nitrophenyl) butoxycarbonyl group, 5- (4-nitrophenyl) pentyloxycarbonyl group, 6- ( 4-nitrophenyl) hexyloxycarbonyl group, 2-amino Benzyloxycarbonyl group, 3-aminobenzyloxycarbonyl group, 4-aminobenzyloxycarbonyl group, 2- (2-aminophenyl) ethoxycarbonyl group, 2- (3-aminophenyl) ethoxycarbonyl group, 2- (4-) Aminophenyl) ethoxycarbonyl group, 3- (4-aminophenyl) propoxycarbonyl group, 4- (4-aminophenyl) butoxycarbonyl group, 5- (4-aminophenyl) pentyloxycarbonyl group, 6- (4-amino) Phenyl) hexyloxycarbonyl group, 2-acetylaminobenzyloxycarbonyl group, 3-propionylaminobenzyloxycarbonyl group, 4-pentanoylaminobenzyloxycarbonyl group, 2- (2-hexanoylaminophenyl) ethoxycarbonyl group, 2 - 3-acetylaminophenyl) ethoxycarbonyl group, 2- (4-acetylaminophenyl) ethoxycarbonyl group, 3- (4-acetylaminophenyl) propoxycarbonyl group, 4- (4-acetylaminophenyl) butoxycarbonyl group, 5 -(4-acetylaminophenyl) pentyloxycarbonyl group, 6- (4-acetylaminophenyl) hexyloxycarbonyl group, 2-ethoxycarbonylbenzyloxycarbonyl group, 3-ethoxycarbonylbenzyloxycarbonyl group, 4-ethoxycarbonylbenzyl group An oxycarbonyl group, 2- (2-ethoxycarbonylphenyl) ethoxycarbonyl group, 2- (3-butoxycarbonylphenyl) ethoxycarbonyl group, 2- (4-propoxycarbonylphenyl) ethoxycal Bonyl group, 3- (4-ethoxycarbonylphenyl) propoxycarbonyl group, 4- (4-pentyloxycarbonylphenyl) butoxycarbonyl group, 5- (4-hexyloxycarbonylphenyl) pentyloxycarbonyl group, 6- (4-ethoxycarbonyl group) Ethoxycarbonylphenyl) hexyloxycarbonyl group, 2- (1,2,3-thiadiazol-4-yl) benzyloxycarbonyl group, 3- (1,2,3-thiadiazol-4-yl) benzyloxycarbonyl group, 4 A phenyl C1-6 alkoxycarbonyl group such as-(1,2,3-thiadiazol-4-yl) benzyloxycarbonyl group (a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group on a phenyl ring, a halogen Substituted or unsubstituted C1-6 alkoxy group, And an amino group which may have one or two C1-6 alkylthio groups, one or two C1-6 alkanoyl groups, a phenyl C1-6 alkoxy group, a C1-6 alkoxycarbonyl group, and a 1,2,2,3 alkoxy group. 1-5, preferably, 1 to 3 groups selected from the group consisting of 3-thiadiazolyl groups may be mentioned.

  Phenyl C3-6 alkenyloxycarbonyl group (on the phenyl ring, a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group And at least one group may be substituted with 1 to 5 groups selected from an unsubstituted phenyl group or a halogen atom, a halogen C1-6 alkyl group, and a halogen substituted or unsubstituted C1-6 alkoxy group And preferably a substituted or unsubstituted phenyl group, an alkenyloxy group having 1 to 3 carbon atoms of 1 to 3 carbon atoms, and a carbonyl group. The phenyl C3-6 alkenyloxycarbonyl group includes both a trans form and a cis form. As such a phenyl C3-6 alkenyloxycarbonyl group, for example, unsubstituted 3-phenyl-2-propenyloxycarbonyl group (conventional name: cinnamyloxycarbonyl group), 4-phenyl-2-butenyloxycarbonyl Group, 4-phenyl-3-butenyloxycarbonyl group, 5-phenyl-2-pentenyloxycarbonyl group, 5-phenyl-4-pentenyloxycarbonyl group, 5-phenyl-3-pentenyloxycarbonyl group, 6-phenyl -5-Hexenyloxycarbonyl group, 6-phenyl-4-hexenyloxycarbonyl group, 6-phenyl-3-hexenyloxycarbonyl group, 4-phenyl-1,3-butadienyloxycarbonyl group, 6-phenyl-1 , 3,5-hexatrienyloxy carbonyl group, 6 Phenyl-3-hexenyloxycarbonyl group, 3- (2-fluorophenyl) -2-propenyloxycarbonyl group, 3- (3-fluorophenyl) -2-propenyloxycarbonyl group, 3- (4-fluorophenyl)- 2-propenyloxycarbonyl group, 3- (2,3-difluorophenyl) -2-propenyloxycarbonyl group, 3- (2,4-difluorophenyl) -2-propenyloxycarbonyl group, 3- (3,4-) Difluorophenyl) -2-propenyloxycarbonyl group, 3- (3,5-difluorophenyl) -2-propenyloxycarbonyl group, 3- (2-chlorophenyl) -2-propenyloxycarbonyl group, 3- (3-chlorophenyl group ) -2-Propenyloxycarbonyl group, 3- (4-chlorophenyl) -2-propenyloxycarbonyl group, 3- (2,3-dichlorophenyl) -2-propenyloxycarbonyl group, 3- (2,4-dichlorophenyl) -2-propenyloxycarbonyl group, 3- (3,4-dichlorophenyl group) ) -2-Propenyloxycarbonyl group, 3- (3,5-dichlorophenyl) -2-propenyloxycarbonyl group, 3- (2-bromophenyl) -2-propenyloxycarbonyl group, 3- (3-bromophenyl) group -2-propenyloxycarbonyl group, 3- (4-bromophenyl) -2-propenyloxycarbonyl group, 3- (2-fluoro-4-bromophenyl) -2-propenyloxycarbonyl group, 3- (2,3 , 4,5,6-pentafluorophenyl) -2-propenyloxycarbonyl group, 3- (4- (4-) Chloro-3-fluorophenyl) -2-propenyloxycarbonyl group, 3- (2,3,4-trichlorophenyl) -2-propenyloxycarbonyl group, 3- (2,4,6-trichlorophenyl) -2- Propenyloxycarbonyl group, 3- (4-isopropylphenyl) -2-propenyloxycarbonyl group, 3- (4-n-butylphenyl) -2-propenyloxycarbonyl group, 3- (2,4-dimethylphenyl)- 2-propenyloxycarbonyl group, 3- (2,3-dimethylphenyl) -2-propenyloxycarbonyl group, 3- (2,6-dimethylphenyl) -2-propenyloxycarbonyl group, 3- (3,5-) Dimethylphenyl) -2-propenyloxycarbonyl group, 3- (2,5-dimethylphenyl) -2-propenyl An oxycarbonyl group, 3- (2,4,6-trimethylphenyl) -2-propenyloxycarbonyl group, 3- (3,5-ditrifluoromethylphenyl) -2-propenyloxycarbonyl group, 3- (4-n) -Butoxyphenyl) -2-propenyloxycarbonyl group, 3- (2,4-dimethoxyphenyl) -2-propenyloxycarbonyl group, 3- (2,3-dimethoxyphenyl) -2-propenyloxycarbonyl group, 3- (2,6-dimethoxyphenyl) -2-propenyloxycarbonyl group, 3- (3,5-dimethoxyphenyl) -2-propenyloxycarbonyl group, 3- (2,5-dimethoxyphenyl) -2-propenyloxycarbonyl Group, 3- (3,5-ditrifluoromethoxyphenyl) -2-propenyloxycar Group, 3- (3-chloro-4-methoxyphenyl-2-propenyloxycarbonyl group, 3- (2-chloro-4-trifluoromethoxyphenyl) -2-propenyloxycarbonyl group, 3- (3-methyl) -4-fluorophenyl) -2-propenyloxycarbonyl group, 3- (4-bromo-3-trifluoromethylphenyl) -2-propenyloxycarbonyl group, 3- (2-methylphenyl) -2-propenyloxycarbonyl Group, 3- (3-methylphenyl) -2-propenyloxycarbonyl group, 3- (4-methylphenyl) -2-propenyloxycarbonyl group, 3- (2-trifluoromethylphenyl) -2-propenyloxycarbonyl Group, 3- (3-trifluoromethylphenyl) -2-propenyloxycarbonyl group, 3- (4-trifluoromethylphenyl) -2-propenyloxycarbonyl group, 3- (2-trifluoromethoxyphenyl) -2-propenyloxycarbonyl group, 3- (3-trifluoromethoxyphenyl) -2-propenyl group Oxycarbonyl group, 3- (4-trifluoromethoxyphenyl) -2-propenyloxycarbonyl group, 3- (2-methoxyphenyl) -2-propenyloxycarbonyl group, 3- (3-methoxyphenyl) -2-propenyl group Oxycarbonyl group, 3- (4-methoxyphenyl) -2-propenyloxycarbonyl group, 3- (3,4-dimethoxyphenyl) -2-propenyloxycarbonyl group, 4- (4-chlorophenyl) -2-butenyl group Oxycarbonyl group, 4- (4-chlorophenyl) -3-butenylo A carbonyl group, 5- (4-chlorophenyl) -2-pentenyloxycarbonyl group, 5- (4-chlorophenyl) -4-pentenyloxycarbonyl group, 5- (4-chlorophenyl) -3-pentenyloxycarbonyl group, 6 -(4-chlorophenyl) -5-hexenyloxycarbonyl group, 6- (4-chlorophenyl) -4-hexenyloxycarbonyl group, 6- (4-chlorophenyl) -2-hexenyloxycarbonyl group, 6- (4-chlorophenyl) group ) -3-hexenyloxycarbonyl group etc. can be mentioned.

  Phenoxycarbonyl group (on the phenyl ring, at least one of a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C May be, for example, phenoxycarbonyl group, 2-fluorophenoxycarbonyl group, 3-fluorophenoxycarbonyl group, 2,3,4,5,6-pentafluorophenoxycarbonyl group, 4-fluorophenoxycarbonyl group, 2-chlorophenoxycarbonyl group, 3-chlorophenoxycarbonyl group, 4-chlorophenoxycarbonyl group, 2,3-dichlorophenoxycarbonyl group, 3,4-dichlorophenoxycarbonyl group, 3,5-dichlorophenoxycarbonyl group, 2- Bromophenoxycarbo Group, 3-bromophenoxycarbonyl group, 4-bromophenoxycarbonyl group, 2-methylphenoxycarbonyl group, 3-methylphenoxycarbonyl group, 4-methylphenoxycarbonyl group, 2-ethylphenoxycarbonyl group, 3-ethylsiphenoxy group Carbonyl group, 4-ethylphenoxycarbonyl group, 4-propylphenoxycarbonyl group, 4-tert-butylphenoxycarbonyl group, 4-butylphenoxycarbonyl group, 2,3-dimethylphenoxycarbonyl group, 3,4,5-trimethylphenoxy Carbonyl group, 4-pentylphenoxycarbonyl group, 4-hexylphenoxycarbonyl group, 2-fluoro-4-bromophenoxycarbonyl group, 4-chloro-3-fluorophenoxycarbonyl group, 2,3,4-tricarbonyl Rolophenoxycarbonyl group, 2,4,6-trichloropheninoxycarbonyl group, 4-isopropylphenoxycarbonyl group, 4-n-butylphenoxycarbonyl group, 2,4-dimethylphenoxycarbonyl group, 2,6-dimethylphenoxycarbonyl Group, 3,5-dimethylphenoxycarbonyl group, 2,5-dimethylphenoxycarbonyl group, 2,4,6-trimethylphenoxycarbonyl group, 3,5-ditrifluoromethylphenoxycarbonyl group, 4-n-butoxyphenoxycarbonyl group 2,4-dimethoxyphenoxycarbonyl group, 2,3-dimethoxyphenoxycarbonyl group, 2,6-dimethoxyphenoxycarbonyl group, 3,5-dimethoxyphenoxycarbonyl group, 2,5-dimethoxyphenoxycarbonyl group, 3, 5-ditrifluoromethoxyphenoxycarbonyl group, 3-chloro-4-methoxyphenoxycarbonyl group, 2-chloro-4-trifluoromethoxyphenoxycarbonyl group, 3-methyl-4-fluorophenoxycarbonyl group, 4-bromo-3- Trifluoromethylphenoxycarbonyl group, 2-trifluoromethylphenoxycarbonyl group, 3-trifluoromethylphenoxycarbonyl group, 4-trifluoromethylphenoxycarbonyl group, 2-pentafluoroethylphenoxycarbonyl group, 3-pentafluoroethylsiphenoxy Carbonyl group, 4-pentafluoroethylphenoxycarbonyl group, 2-methoxyphenoxycarbonyl group, 3-methoxyphenoxycarbonyl group, 4-methoxyphenoxycarbonyl group, 2-ethoxy Phenoxycarbonyl group, 3-ethoxyphenoxycarbonyl group, 4-ethoxyphenoxycarbonyl group, 4-propoxyphenoxycarbonyl group, 4-tert-butoxyphenoxycarbonyl group, 4-n-butoxyphenoxycarbonyl group, 3,4,5-tri Methoxy phenoxycarbonyl group, 4-pentoxy phenoxycarbonyl group, 4-hexyl oxy phenoxycarbonyl group, 2- trifluoro methoxy phenoxycarbonyl group, 3- trifluoro methoxy phenoxycarbonyl group, 4- trifluoro methoxy phenoxycarbonyl group, 2- Phenoxy carbonyl such as penta fluoro ethoxy phenoxycarbonyl group, 3 penta fluoro ethoxy phenoxycarbonyl group, 4 penta fluoro ethoxy phenoxycarbonyl group (On the phenyl ring, 1 to 5 groups, preferably 1 to 6 groups selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group are preferred. 3) may be mentioned.

  Phenyl C1-6 alkyl carbamoyl group (on the phenyl ring, at least one of a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group As 1 type may be substituted, for example, benzylcarbamoyl group, 2-phenethylcarbamoyl group, 3-phenylpropylcarbamoyl group, 2-phenylpropylcarbamoyl group, 4-phenylbutylcarbamoyl group, 5-phenylpentylcarbamoyl group 4-phenylpentylcarbamoyl group, 6-phenylhexylcarbamoyl group, 2-fluorobenzylcarbamoyl group, 3-fluorobenzylcarbamoyl group, 4-fluorobenzylcarbamoyl group, 2-chlorobenzylcarbamoyl group, 3- Rorobenzylcarbamoyl group, 4-chlorobenzylcarbamoyl group, 2-bromobenzylcarbamoyl group, 3-bromobenzylcarbamoyl group, 4-bromobenzylcarbamoyl group, 2-iodobenzylcarbamoyl group, 3-iodobenzylcarbamoyl group, 4-iodo Benzylcarbamoyl group, N-benzyl-N-methylcarbamoyl group, N-methyl-N- (2-phenethyl) carbamoyl group, N-methyl-N- (3-phenylpropyl) carbamoyl group, N-methyl-N- ( 2-phenylpropyl) carbamoyl group, N-methyl-N- (4-phenylbutyl) carbamoyl group, N-methyl-N- (5-phenylpentyl) carbamoyl group, N-methyl-N- (4-phenylpentyl) Carbamoyl group, N-methyl-N- (6-phenyl Xyl) carbamoyl group, N- (2-fluorobenzyl) -N-methylcarbamoyl group, N- (3-fluorobenzyl) -N-methylcarbamoyl group, N- (4-fluorobenzyl) -N-methylcarbamoyl group, N- (2-chlorobenzyl) -N-methylcarbamoyl group, N- (3-chlorobenzyl) -N-methylcarbamoyl group, N- (4-chlorobenzyl) -N-methylcarbamoyl group, N- (2-chlorobenzyl) Bromobenzyl) -N-methylcarbamoyl group, N- (3-bromobenzyl) -N-methylcarbamoyl group, N- (4-bromobenzyl) -N-methylcarbamoyl group, N, N-dibenzylcarbamoyl group, N -Benzyl-N- (2-phenethyl) carbamoyl group, N-benzyl- (3-phenylpropyl) carbamoyl group, N-benzyl alcohol N-benzyl-N- (4-phenylbutyl) carbamoyl group, N-benzyl-N- (5-phenylpentyl) carbamoyl group, N-benzyl-N- ( 4-phenylpentyl) carbamoyl group, N-benzyl-N- (6-phenylhexyl) carbamoyl group, N-benzyl-N- (2-fluorobenzyl) carbamoyl group, N-benzyl-N- (3-fluorobenzyl) Carbamoyl group, N-benzyl-N- (4-fluorobenzyl) carbamoyl group, N-benzyl-N- (2-chlorobenzyl) carbamoyl group, N-benzyl-N- (3-chlorobenzyl) carbamoyl group, N- Benzyl-N- (4-chlorobenzyl) carbamoyl group, N-benzyl-N- (2-bromobenzyl) carba Group, N-benzyl-N- (3-bromobenzyl) carbamoyl group, N-benzyl-N- (4-bromobenzyl) carbamoyl group, 2,3-difluorobenzylcarbamoyl group, 3,4-difluorobenzylcarbamoyl group , 3,5-difluorobenzylcarbamoyl group, 2,4-difluorobenzylcarbamoyl group, 2,6-difluorobenzylcarbamoyl group, 2,3-dichlorobenzylcarbamoyl group, 3,4-dichlorobenzylcarbamoyl group, 3,5- Dichlorobenzylcarbamoyl group, 2,4-dichlorobenzylcarbamoyl group, 2,6-dichlorobenzylcarbamoyl group, 2-fluoro-4-bromobenzylcarbamoyl group, 4-chloro-3-fluorobenzylcarbamoyl group, 2,3,4 -Trichlorobenzylcarbamo Group, 3,4,5-trifluorobenzylcarbamoyl group, 2,4,6-trichlorobenzylcarbamoyl group, 4-isopropylbenzylcarbamoyl group, 4-n-butylbenzylcarbamoyl group, 4-methylbenzylcarbamoyl group, 2 -Methylbenzylcarbamoyl group, 3-methylbenzylcarbamoyl group, 2,4-dimethylbenzylcarbamoyl group, 2,3-dimethylbenzylcarbamoyl group, 2,6-dimethylbenzylcarbamoyl group, 3,5-dimethylbenzylcarbamoyl group, 2 5-dimethylbenzylcarbamoyl group, 2,4,6-trimethylbenzylcarbamoyl group, 3,5-ditrifluoromethylbenzylcarbamoyl group, 4-isopropoxybenzylcarbamoyl group, 4-n-butoxybenzylcarbamoyl group, 4-methane Hydroxybenzylcarbamoyl group, 2-methoxybenzylcarbamoyl group, 3-methoxybenzylcarbamoyl group, 2,4-dimethoxybenzylcarbamoyl group, 2,3-dimethoxybenzylcarbamoyl group, 2,6-dimethoxybenzylcarbamoyl group, 3,5- Dimethoxybenzylcarbamoyl group, 2,5-dimethoxybenzylcarbamoyl group, 2,4,6-trimethoxybenzylcarbamoyl group, 3,5-ditrifluoromethoxybenzylcarbamoyl group, 2-isopropoxybenzylcarbamoyl group, 3-chloro-4 -Methoxybenzylcarbamoyl group, 2-chloro-4-trifluoromethoxybenzylcarbamoyl group, 3-methyl-4-fluorobenzylcarbamoyl group, 4-bromo-3-trifluoromethylbenzylcarbamoyl group , 2-trifluoromethylbenzylcarbamoyl group, 3-trifluoromethylbenzylcarbamoyl group, 4-trifluoromethylbenzylcarbamoyl group, 2-pentafluoroethylbenzylcarbamoyl group, 3-pentafluoroethylbenzylcarbamoyl group, 4-pentafluoro Ethylbenzylcarbamoyl group, 2-trifluoromethoxybenzylcarbamoyl group, 3-trifluoromethoxybenzylcarbamoyl group, 4-trifluoromethoxybenzylcarbamoyl group, 2-pentafluoroethoxybenzylcarbamoyl group, 3-pentafluoroethoxybenzylcarbamoyl group, 4-Pentafluoroethoxybenzylcarbamoyl group, 2- (2-trifluoromethylphenyl) ethylcarbamoyl group, 2- (3-trifluoromethyl) Phenyl) ethylcarbamoyl group, 2- (4-trifluoromethylphenyl) ethylcarbamoyl group, 2- (2-trifluoromethoxyphenyl) ethylcarbamoyl group, 2- (3-trifluoromethoxyphenyl) ethylcarbamoyl group, 2- (4-trifluoromethoxyphenyl) ethylcarbamoyl group, 2- (2-pentafluoroethoxyphenyl) ethylcarbamoyl group, 2- (3-pentafluoroethoxyphenyl) ethylcarbamoyl group, 2- (4-pentafluoroethoxyphenyl) group Ethylcarbamoyl group, 3- (2-trifluoromethylphenyl) propylcarbamoyl group, 3- (3-trifluoromethylphenyl) propylcarbamoyl group, 3- (4-trifluoromethylphenyl) propyl group carbamoyl, 3- (2 - Trifluoromethoxyphenyl) propylcarbamoyl group, 3- (3-trifluoromethoxyphenyl) propylcarbamoyl group, 3- (4-trifluoromethoxyphenyl) propylcarbamoyl group, 3- (3-pentafluoroethoxyphenyl) propylcarbamoyl group 3- (4-Pentafluoroethoxyphenyl) propylcarbamoyl group, 4- (3-pentafluoroethoxyphenyl) butylcarbamoyl group, 5- (4-trifluoromethylphenyl) pentylcarbamoyl group, 4- (4-trifluoro) Methylphenyl) pentylcarbamoyl group, 4- (4-trifluoromethoxyphenyl) pentylcarbamoyl group, 6- (3-trifluoromethylphenyl) hexylcarbamoyl group, 6- (4-trifluoromethylphenyl) group Phenyl C1-6 alkylcarbamoyl groups such as xylcarbamoyl group, 6- (4-trifluoromethoxyphenyl) hexyl carbamoyl group (on the phenyl ring, halogen atoms, halogen substituted or unsubstituted C1-6 alkyl groups and halogen substituted Or 1 to 5, preferably 1 to 3 groups selected from the group consisting of unsubstituted C1-6 alkoxy groups may be mentioned.

  Examples of the benzofuryl-substituted C1-6 alkoxycarbonyl group (at least one halogen atom may be substituted on the benzofuran ring) include, for example, 2-benzofurylmethoxycarbonyl group, 1- (2-benzofuryl) Ethoxycarbonyl group, 2- (4-benzofuryl) ethoxycarbonyl group, 3- (5-benzofuryl) propoxycarbonyl group, 4- (6-benzofuryl) butoxycarbonyl group, 5- (7-benzofuryl) pentyloxycarbonyl group, 6 -(2-benzofuryl) hexyloxycarbonyl group, 4-fluoro-2-benzofurylmethoxycarbonyl group, 5-fluoro-2-benzofurylmethoxycarbonyl group, 6-fluoro-2-benzofurylmethoxycarbonyl group, 7-fluoro -2-benzofuryl methoxycal Group, 4-chloro-2-benzofurylmethoxycarbonyl group, 5-chloro-2-benzofurylmethoxycarbonyl group, 6-chloro-2-benzofurylmethoxycarbonyl group, 7-chloro-2-benzofurylmethoxycarbonyl group 4-bromo-2-benzofurylmethoxycarbonyl group, 5-bromo-2-benzofurylmethoxycarbonyl group, 6-bromo-2-benzofurylmethoxycarbonyl group, 7-bromo-2-benzofurylmethoxycarbonyl group, 4 -Iodo-2-benzofurylmethoxycarbonyl group, 5-iodo-2-benzofurylmethoxycarbonyl group, 6-iodo-2-benzofurylmethoxycarbonyl group, 7-iodo-2-benzofurylmethoxycarbonyl group, 4-fluoro -3-benzofurylmethoxycarbonyl group, 5- Luoro-3-benzofurylmethoxycarbonyl group, 6-fluoro-3-benzofurylmethoxycarbonyl group, 7-fluoro-3-benzofurylmethoxycarbonyl group, 4-chloro-3-benzofurylmethoxycarbonyl group, 5-chloro- 3-benzofurylmethoxycarbonyl group, 6-chloro-3-benzofurylmethoxycarbonyl group, 7-chloro-3-benzofurylmethoxycarbonyl group, 4-bromo-3-benzofurylmethoxycarbonyl group, 5-bromo-3- Benzofuryl methoxycarbonyl group, 6-bromo-3-benzofuryl methoxycarbonyl group, 7-bromo-3-benzofuryl methoxycarbonyl group, 4-iodo-3-benzofuryl methoxycarbonyl group, 5-iodo-3-benzofuryl Methoxy carbonyl group, 6-iodo-3- Benzofuryl methoxycarbonyl group, 7-iodo-3-benzofuryl methoxycarbonyl group, 2- (4-fluoro-2-benzofuryl) ethoxycarbonyl group, 2- (5-fluoro-2-benzofuryl) ethoxycarbonyl group, 2- (6-fluoro-2-benzofuryl) ethoxycarbonyl group, 2- (7-fluoro-2-benzofuryl) ethoxycarbonyl group, 2- (4-chloro-2-benzofuryl) ethoxycarbonyl group, 2- (5-chloro-) 2-benzofuryl) ethoxycarbonyl group, 2- (6-chloro-2-benzofuryl) ethoxycarbonyl group, 2- (7-chloro-2-benzofuryl) ethoxycarbonyl group, 2- (4-fluoro-3-benzofuryl) ethoxy Carbonyl group, 2- (5-fluoro-3-benzofuryl) ethoxycal 2- (6-fluoro-3-benzofuryl) ethoxycarbonyl group, 2- (7-fluoro-3-benzofuryl) ethoxycarbonyl group, 2- (4-chloro-3-benzofuryl) ethoxycarbonyl group, 2- (5-chloro-3-benzofuryl) ethoxycarbonyl group, 2- (6-chloro-3-benzofuryl) ethoxycarbonyl group, 2- (7-chloro-3-benzofuryl) ethoxycarbonyl group, 6- (4-fluoro-) 2-benzofuryl) hexyloxycarbonyl group, 6- (5-fluoro-2-benzofuryl) hexyloxycarbonyl group, 6- (6-fluoro-2-benzofuryl) hexyloxycarbonyl group, 6- (7-fluoro-2-) Benzofuryl) hexyloxycarbonyl group, 6- (4-chloro-2-benzofuryl) hexene Roxycarbonyl, 6- (5-chloro-2-benzofuryl) hexyloxycarbonyl, 6- (6-chloro-2-benzofuryl) hexyloxycarbonyl, 6- (7-chloro-2-benzofuryl) hexyloxy Carbonyl group, 6- (4-fluoro-3-benzofuryl) methoxycarbonyl group, 6- (5-fluoro-3-benzofuryl) hexyloxycarbonyl group, 6- (6-fluoro-3-benzofuryl) hexyloxycarbonyl group, 6- (7-fluoro-3-benzofuryl) hexyloxycarbonyl group, 6- (4-chloro-3-benzofuryl) hexyloxycarbonyl group, 6- (5-chloro-3-benzofuryl) hexyloxycarbonyl group, 6- (6-chloro-3-benzofuryl) hexyloxycarbonyl group, 6 Benzofuran rings such as-(7-chloro-3-benzofuryl) hexyloxycarbonyl group, (2,4-dibromo-3-benzofuryl) methoxycarbonyl group, (4,5,6-trichloro-3-benzofuryl) methoxycarbonyl group, etc. Mention may be made of a benzofuryl-substituted C1-6 alkoxycarbonyl group which may be substituted by 1 to 3 halogen atoms.

  A benzothienyl C1-6 alkoxycarbonyl group (on the benzothiophene ring, at least one of a group selected from the group consisting of a halogen atom and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted) Are, for example, 2-benzothienylmethoxycarbonyl group, 3-benzothienylmethoxycarbonyl group, 4-benzothienylmethoxycarbonyl group, 5-benzothienylmethoxycarbonyl group, 6-benzothienylmethoxycarbonyl group, 7-benzothienylmethoxy Carbonyl group, 2- (2-benzothienyl) ethoxycarbonyl group, 3- (2-benzothienyl) propoxycarbonyl group, 4- (2-benzothienyl) butoxycarbonyl group, 5- (2-benzothienyl) pentyloxycarbonyl 6- (2- Benzothienyl) hexyloxycarbonyl group, 5-trifluoromethoxy-2-benzothienylmethoxycarbonyl group, 5-trifluoromethoxy-3-benzothienylmethoxycarbonyl group, 5-trifluoromethoxy-4-benzothienylmethoxycarbonyl group, 4 -Trifluoromethoxy-5-benzothienylmethoxycarbonyl group, 3-trifluoromethoxy-6-benzothienylmethoxycarbonyl group, 2-trifluoromethoxy-7-benzothienylmethoxycarbonyl group, 2-methoxy-7-benzothienyl methoxy Carbonyl group, 5,6-dimethoxy-3-benzothienylmethoxycarbonyl group, 2,5,6-trimethoxy-3-benzothienylmethoxycarbonyl group, 5-chloro-6-methoxy-3-benzothienyl group Xycarbonyl group, 2- (4-ethoxy-2-benzothienyl) ethoxycarbonyl group, 5-chloro-3-benzothienylmethoxycarbonyl group, 3,4-dibromo-2-benzothienylmethoxycarbonyl group, 4,5,5 Benzothienyl C.sub.1-6 alkoxycarbonyl groups such as 6-trichloro-2-benzothienylmethoxycarbonyl group, 5-trifluoromethoxy-2-chloro-7-benzothienylmethoxycarbonyl group, etc. (as substituents on the benzothiophene ring And 1 to 3 groups selected from the group consisting of a halogen atom and a halogen-substituted or unsubstituted C1-6 alkoxy group may be mentioned.

  As a naphthyl substituted C1-6 alkoxycarbonyl group, for example, 1-naphthyl methoxycarbonyl group, 2-naphthyl methoxycarbonyl group, 2- (1-naphthyl) ethoxycarbonyl group, 2- (2-naphthyl) ethoxycarbonyl group, 3 -(1-naphthyl) propoxycarbonyl group, 3- (2-naphthyl) propoxycarbonyl group, 4- (1-naphthyl) butoxycarbonyl group, 4- (2-naphthyl) butoxycarbonyl group, 5- (1-naphthyl) group Examples thereof include pentoxy carbonyl group, 5- (2-naphthyl) pentoxy carbonyl group, 6- (1-naphthyl) hexyl oxycarbonyl group, 6- (2-naphthyl) hexyl oxycarbonyl group and the like.

  Examples of the pyridyl substituted C1-6 alkoxycarbonyl group (in which at least one halogen atom may be substituted on the pyridine ring) include, for example, 2-pyridylmethoxycarbonyl group, 3-pyridylmethoxycarbonyl group, 4- Pyridyl methoxycarbonyl group, 2- (2-pyridyl) ethoxycarbonyl group, 2- (3-pyridyl) ethoxycarbonyl group, 2- (4-pyridyl) ethoxycarbonyl group, 3- (2-pyridyl) propoxycarbonyl group, 3 -(3-Pyridyl) propoxycarbonyl group, 3- (4-pyridyl) propoxycarbonyl group, 4- (2-pyridyl) butoxycarbonyl group, 4- (3-pyridyl) butoxycarbonyl group, 4- (4-pyridyl) group Butoxycarbonyl group, 5- (2-pyridyl) pentyloxycarbonyl group, 5 (3-pyridyl) pentyloxycarbonyl group, 5- (4-pyridyl) pentyloxycarbonyl group, 6- (2-pyridyl) hexyloxycarbonyl group, 6- (3-pyridyl) hexyloxycarbonyl group, 6- (4) -Pyridyl) hexyloxycarbonyl group, 2-chloro-3-pyridylmethoxycarbonyl group, 3-bromo-2-pyridylmethoxycarbonyl group, 4-fluoro-2-pyridylmethoxycarbonyl group, 2- (2-chloro-4- Pyridyl) ethoxycarbonyl group, 2- (3-chloro-5-pyridyl) ethoxycarbonyl group, 2- (4-iodo-3-pyridyl) ethoxycarbonyl group, 3- (2-bromo-5-pyridyl) propoxycarbonyl group , 3- (3-fluoro-4-pyridyl) propoxycarbonyl group, 3- (4-qu) Ro-2-pyridyl) propoxycarbonyl group, 4- (2-iodo-5-pyridyl) butoxycarbonyl group, 4- (3-bromo-5-pyridyl) butoxycarbonyl group, 4- (4-chloro-5-pyridyl) group ) 5-Butoxycarbonyl group, 5- (2-chloro-5-pyridyl) pentyloxycarbonyl group, 5- (3-fluoro-2-pyridyl) pentyloxycarbonyl group, 5- (4-bromo-2-pyridyl) pentyloxy Carbonyl group, 6- (2-chloro-5-pyridyl) hexyloxycarbonyl group, 6- (3-fluoro-4-pyridyl) hexyloxycarbonyl group, 6- (4-bromo-2-pyridyl) hexyloxycarbonyl group , (2,6-dichloro-4-pyridyl) methoxycarbonyl group, (2,3,4-trichloro-6-pyridyl) Pyridyl-substituted C1-6 alkoxycarbonyl groups such as a toxoxycarbonyl group (1 to 3 halogen atoms may be substituted as substituents on a pyridine ring).

  Examples of the furyl-substituted C1-6 alkoxycarbonyl group (in which at least one nitro group may be substituted on the furan ring) include, for example, 2-furyl methoxycarbonyl group, 3-furyl methoxycarbonyl group, 2- (2-furyl) ethoxycarbonyl group, 3- (2-furyl) propoxycarbonyl group, 3- (3-furyl) propoxycarbonyl group, 4- (2-furyl) butoxycarbonyl group, 4- (3-furyl) butoxy Carbonyl group, 5- (2-furyl) pentyloxycarbonyl group, 5- (3-furyl) pentyloxycarbonyl group, 6- (2-furyl) hexyloxycarbonyl group, 6- (3-furyl) hexyloxycarbonyl group , 5-nitro-2-furylmethoxycarbonyl group, 5-nitro-3-furylmethoxycarbonyl group, 2- 5-nitro-2-furyl) ethoxycarbonyl group, 3- (5-nitro-2-furyl) propoxycarbonyl group, 4- (5-nitro-2-furyl) butoxycarbonyl group, 4- (5-nitro-3) -Furyl) butoxycarbonyl group, 5- (5-nitro-2-furyl) pentyloxycarbonyl group, 5- (5-nitro-3-furyl) pentyloxycarbonyl group, 6- (5-nitro-2-furyl) group Hexyloxycarbonyl group, 6- (5-nitro-3-furyl) hexyloxycarbonyl group, (4,5-dinitro-2-furyl) methoxycarbonyl group, (2,4,5-trinitro-3-furyl) methoxy Furyl-substituted C.sub.1-6 alkoxycarbonyl groups such as carbonyl groups (1 to 3 nitro groups may be substituted as substituents on the furan ring) Rukoto can.

  Examples of the thienyl-substituted C1-6 alkoxycarbonyl group (on the thiophene ring, at least one halogen atom may be substituted) include, for example, 2-thienylmethoxycarbonyl group, 3-thienylmethoxycarbonyl group, 2- (2-thienyl) ethoxycarbonyl group, 3- (2-thienyl) propoxycarbonyl group, 3- (3-thienyl) propoxycarbonyl group, 4- (2-thienyl) butoxycarbonyl group, 4- (3-thienyl) butoxy Carbonyl group, 5- (2-thienyl) pentyloxycarbonyl group, 5- (3-thienyl) pentyloxycarbonyl group, 6- (2-thienyl) hexyloxycarbonyl group, 6- (3-thienyl) hexyloxycarbonyl group , 5-chloro-2-thienylmethoxycarbonyl group, 5-chloro-3 Thienyl methoxycarbonyl group, 2- (4-bromo-2-thienyl) ethoxycarbonyl group, 3- (3-fluoro-2-thienyl) propoxycarbonyl group, 4- (5-iodo-2-thienyl) butoxycarbonyl group, 4- (4-chloro-3-thienyl) butoxycarbonyl group, 5- (3-chloro-2-thienyl) pentyloxycarbonyl group, 5- (2-chloro-3-thienyl) pentyloxycarbonyl group, 6- (6) 3-chloro-2-thienyl) hexyloxycarbonyl group, 6- (5-chloro-3-thienyl) hexyloxycarbonyl group, (4,5-dichloro-2-thienyl) methoxycarbonyl group, (2,4,5 Thienyl-substituted C1-6 alkoxycarbonyl groups such as -trichloro-3-thienyl) methoxycarbonyl group (thiophene The upper, and a halogen atom may be a have 1-3) as a substituent.

  From a thiazolyl-substituted C.sub.1-6 alkoxycarbonyl group (a C.sub.1-6 alkyl group and a phenyl group on the thiazole ring [a halogen substituted or unsubstituted C.sub.1-6 alkyl group may be substituted on the phenyl ring]) As at least one group selected from the group consisting of) may be, for example, 2-thiazolyl methoxycarbonyl group, 2- (2-thiazolyl) ethoxycarbonyl group, 3- (2-thiazolyl group) ) Propoxycarbonyl group, 4- (2-thiazolyl) butoxycarbonyl group, 5- (2-thiazolyl) pentyloxycarbonyl group, 6- (2-thiazolyl) hexyloxycarbonyl group, 4-thiazolylmethoxycarbonyl group, 5 -Thiazolyl methoxycarbonyl group, 2-methyl-4-thiazolyl methoxycarbonyl group, 2-methyl 5-thiazolylmethoxycarbonyl group, 5-methyl-2-thiazolylmethoxycarbonyl group, 4-methyl-2-thiazolylmethoxycarbonyl group, 5-methyl-4-thiazolylmethoxycarbonyl group, 4- Methyl-5-thiazolylmethoxycarbonyl group, 2-ethyl-4-thiazolylmethoxycarbonyl group, 2-ethyl-5-thiazolylmethoxycarbonyl group, 5-ethyl-2-thiazolylmethoxycarbonyl group, 5-propyl-2-thiazolylmethoxycarbonyl group, 4-n-butyl-2-thiazolylmethoxycarbonyl group, 5-ethyl-4-thiazolylmethoxycarbonyl group, 4-n-pentyl-5-thia group Zoryl methoxycarbonyl group, 2-n-hexyl-4-thiazolyl methoxycarbonyl group, 2-n-hexyl-5-thiazolyl group Xycarbonyl group, 4-n-pentyl-2-thiazolyl methoxycarbonyl group, 5-n-hexyl-2-thiazolyl methoxycarbonyl group, 4-n-hexyl-2-thiazolyl methoxycarbonyl group, 5 -N-Hexyl-4-thiazolyl methoxycarbonyl group, 4-n-hexyl-5-thiazolyl methoxycarbonyl group, 2-phenyl-4-thiazolyl methoxycarbonyl group, 2-phenyl-5-thiazole group 4-methoxy-2-thiazolyl methoxycarbonyl, 4-phenyl-2-thiazolyl methoxycarbonyl, 5-phenyl-2-thiazolyl methoxycarbonyl, 2- (4-phenyl) -2-thiazolyl) ethoxycarbonyl group, 5-phenyl-4-thiazolylmethoxycarbonyl group, 4-phenyl-5-thiol Azolyl methoxycarbonyl group, 5- (2-fluorophenyl) -2-thiazolylmethoxycarbonyl group, 5- (2-fluorophenyl) -4-thiazolylmethoxycarbonyl group, 4- (2-fluorophenyl) group -5-thiazolylmethoxycarbonyl group, 2- (2-bromophenyl) -4-thiazolylmethoxycarbonyl group, 2- (2-fluorophenyl) -5-thiazolylmethoxycarbonyl group, 2- (3) -Chlorophenyl) -4-thiazolylmethoxycarbonyl group, 2- (2,3-difluorophenyl) -5-thiazolylmethoxycarbonyl group, 2- (2,4-dibromophenyl) -4-thiazolylmethoxy Carbonyl group, 4- (2,5-dichlorophenyl) -5-thiazolylmethoxycarbonyl group, 2- (2-chlorophenyl) -4- 4 Azolyl methoxycarbonyl group, 2- (2,4,6-trichlorophenyl) -5-thiazolylmethoxycarbonyl group, 2- (4-chlorophenyl) -4-thiazolylmethoxycarbonyl group, 2- (2- (2-chlorophenyl) group Fluorophenyl) -5-thiazolylmethoxycarbonyl group, 2- (4-chlorophenyl) -5-thiazolylmethoxycarbonyl group, 2- (2,4-dichlorophenyl) -5-thiazolylmethoxycarbonyl group, 4 -(2-Methylphenyl) -5-thiazolylmethoxycarbonyl group, 2- (2-ethylphenyl) -4-thiazolylmethoxycarbonyl group, 2- (2-n-propylphenyl) -5-thiazole group And 2- (3-isopropylphenyl) -4-thiazolylmethoxycarbonyl group, 2- (3-n-butylphenyne) ) 5-thiazolyl methoxycarbonyl group, 2- (4-n-pentylphenyl) -4-thiazolyl methoxycarbonyl group, 4- (2-n-hexylphenyl) -5-thiazolyl methoxycarbonyl group , 2- (2,4-dimethylphenyl) -4-thiazolylmethoxycarbonyl group, 2- (2,3-dimethylphenyl) -5-thiazolylmethoxycarbonyl group, 2- (2,4,6-) Trimethylphenyl) -4-thiazolylmethoxycarbonyl group, 2- (2-methylphenyl) -4-methyl-5-thiazolylmethoxycarbonyl group, 2- (4-chlorophenyl) -5-methyl-4-thia Zoryl methoxycarbonyl group, 2,4-dimethyl-5-thiazolyl methoxycarbonyl group, 5- (2-trifluoromethylphenyl) -2-thiazolyl methoxy group Rubonyl, 5- (2-trifluoromethylphenyl) -4-thiazolylmethoxycarbonyl, 4- (2-trifluoromethylphenyl) -5-thiazolylmethoxycarbonyl, 2- (2-trifluoro) Methylphenyl) -4-thiazolylmethoxycarbonyl group, 2- (2-trifluoromethylphenyl) -5-thiazolylmethoxycarbonyl group, 2- (3-trifluoromethylphenyl) -4-thiazolylmethoxy Thiazolyl-substituted C1-6 alkoxy such as carbonyl group, 2- (3-trifluoromethylphenyl) -5-thiazolylmethoxycarbonyl group, 2- (4-trifluoromethylphenyl) -4-thiazolylmethoxycarbonyl group, etc. A carbonyl group (on the thiazole ring, a C 1 to 6 alkyl group and a phenyl group [on the phenyl ring Or two or more groups selected from the group consisting of 1 to 5, preferably 1 to 3 substituted C1-6 alkyl groups which may be gen-substituted or unsubstituted] Can be mentioned.

  A tetrazolyl-substituted C.sub.1-6 alkoxycarbonyl group (on the tetrazole ring, a C.sub.1-6 alkyl group and a phenyl group, and on the phenyl ring, at least one halogen atom may be substituted), As at least one kind of the substituted groups) may be, for example, 5- (1H) -tetrazolylmethoxycarbonyl group, 2- (5- (1H) -tetrazolyl) ethoxycarbonyl group, 3- (3) 5- (1H) -tetrazolyl) propoxycarbonyl group, 4- (5- (1H) -tetrazolyl) butoxycarbonyl group, 5- (5- (1H) -tetrazolyl) pentyloxycarbonyl group, 6- (5- (1H) ) -Tetrazolyl) hexyloxycarbonyl group, 1-methyl-5- (1H) -tetrazolylmethoxycarbonyl group, 1-ethyl- -(1H) -tetrazolylmethoxycarbonyl group, 1-n-propyl-5- (1H) -tetrazolylmethoxycarbonyl group, 1-n-butyl-5- (1H) -tetrazolylmethoxycarbonyl group, 1-n-Pentyl-5- (1H) -tetrazolylmethoxycarbonyl group, 1-n-hexyl-5- (1H) -tetrazolylmethoxycarbonyl group, 1-phenyl-5- (1H) -tetrazoli group 1- (2-fluorophenyl) -5- (1H) -tetrazolylmethoxycarbonyl group, 1- (3-fluorophenyl) -5- (1H) -tetrazolylmethoxycarbonyl group, 1 -(4-fluorophenyl) -5- (1H) -tetrazolylmethoxycarbonyl group, 1- (2-chlorophenyl) -5- (1H) -tetrazolyl methoxyl Carbonyl group, 1- (3-chlorophenyl) -5- (1H) -tetrazolylmethoxycarbonyl group, 1- (4-chlorophenyl) -5- (1H) -tetrazolylmethoxycarbonyl group, 1- (2- (2-chlorophenyl) -5- (1H) -tetrazolylmethoxycarbonyl group; Bromophenyl) -5- (1H) -tetrazolylmethoxycarbonyl group, 1- (3-bromophenyl) -5- (1H) -tetrazolylmethoxycarbonyl group, 1- (4-bromophenyl) -5- (1H) -tetrazolylmethoxycarbonyl group, 2- (1-methyl-5- (1H) -tetrazolyl) ethoxycarbonyl group, 2- (1-ethyl-5- (1H) -tetrazolyl) ethoxycarbonyl group, 2 -(1-propyl-5- (1H) -tetrazolyl) methoxycarbonyl group, 2- (1-butyl-5- (1H) -tetrazolyl) ethoxycarbonyl group , 2- (1-pentyl-5- (1H) -tetrazolyl) ethoxycarbonyl group, 2- (1-hexyl-5- (1H) -tetrazolyl) ethoxycarbonyl group, 2- (1-phenyl-5- (1H) ) -Tetrazolyl) ethoxycarbonyl group, 2- (1- (2,4-difluorophenyl) -5- (1H) -tetrazolyl) ethoxycarbonyl group, 2- (1- (3-fluorophenyl) -5- (1H) ) -Tetrazolyl) ethoxycarbonyl group, 2- (1- (4-fluorophenyl) -5- (1H) -tetrazolyl) ethoxycarbonyl group, 2- (1- (2,4,6-trichlorophenyl) -5-carbonyl group (1H) -tetrazolyl) ethoxycarbonyl group, 2- (1- (3-chlorophenyl) -5- (1H) -tetrazolyl) ethoxycarbonyl group, 2- (1-) 4-chlorophenyl) -5- (1H) -tetrazolyl) ethoxycarbonyl group, 2- (1- (2-bromophenyl) -5- (1H) -tetrazolyl) ethoxycarbonyl group, 2- (1- (3-bromo) group Tetrazolyl-substituted C1-6 alkoxycarbonyl groups (tetrazole such as phenyl) -5- (1H) -tetrazolyl) ethoxycarbonyl group, 2- (1- (4-bromophenyl) -5- (1H) -tetrazolyl) ethoxycarbonyl group, etc. The ring is selected from the group consisting of a C1-6 alkyl group as a substituent and a phenyl group [1 to 5, preferably 1 to 3 halogen atoms may be substituted on the phenyl ring]. And the substituted group may be substituted by 1 to 3).

  As the 2,3-dihydro-1H-indenyloxycarbonyl group, for example, 2,3-dihydro-1H-inden-1-yloxycarbonyl group, 2,3-dihydro-1H-inden-2-yloxycarbonyl And the like.

  Examples of the adamantane-substituted C1-6 alkoxycarbonyl group include adamantan-1-ylmethoxycarbonyl group, 2- (adamantan-1-yl) ethoxycarbonyl group, 3- (adamantan-1-yl) propoxycarbonyl group, 4- Examples include (adamantan-1-yl) butoxycarbonyl group, 5- (adamantan-1-yl) pentyloxycarbonyl group, 6- (adamantan-1-yl) hexyloxycarbonyl group and the like.

  As the phenyl C3-6 alkynyloxycarbonyl group, for example, 2-phenylethynyloxycarbonyl group, 3-phenyl-2-propynyloxycarbonyl group, 4-phenyl-3-butyn-1-yloxycarbonyl group, 4-phenyl Examples thereof include a 3-butyn-2-yloxycarbonyl group, a 5-phenyl-4-pentyn-1-yloxycarbonyl group, a 6-phenyl-5-hexyn-1-yloxycarbonyl group and the like.

  As phenylthio C1-6 alkoxycarbonyl group, for example, phenylthiomethoxycarbonyl group, 2-phenylthioethoxycarbonyl group, 1-phenylthioethoxycarbonyl group, 3- (phenylthio) propoxycarbonyl group, 4- (phenylthio) butoxycarbonyl group And 5- (phenylthio) pentyloxycarbonyl group, 6- (phenylthio) hexyloxycarbonyl group and the like can be mentioned.

  As phenyl C1-6 alkoxy substituted C1-6 alkoxy carbonyl group, for example, benzyloxy methoxy carbonyl group, 2-benzyloxy ethoxy carbonyl group, 3- (benzyloxy) propoxycarbonyl group, 4- (benzyloxy) butoxycarbonyl group , 5- (benzyloxy) pentyloxycarbonyl group, 6- (benzyloxy) hexyloxycarbonyl group, 2-phenylethoxymethoxycarbonyl group, 2-phenylethoxyethoxycarbonyl group, 3- (2-phenylethoxy) propoxycarbonyl group 4- (2-phenylethoxy) butoxycarbonyl group, 5- (2-phenylethoxy) pentyloxycarbonyl group, 6- (2-phenylethoxy) hexyloxycarbonyl group, 3-phenylpropoxy group Xycarbonyl group, 3-phenylpropoxyethoxycarbonyl group, 3- (3-phenylpropoxy) propoxycarbonyl group, 4- (3-phenylpropoxy) butoxycarbonyl group, 5- (3-phenylpropoxy) pentyloxycarbonyl group, 6 -(3-phenylpropoxy) hexyloxycarbonyl group, 4-phenylbutoxymethoxycarbonyl group, 4-phenylbutoxyethoxycarbonyl group, 3- (4-phenylbutoxy) propoxycarbonyl group, 4- (4-phenylbutoxy) butoxycarbonyl group Group, 5- (4-phenylbutoxy) pentyloxycarbonyl group, 6- (4-phenylbutoxy) hexyloxycarbonyl group, 5-phenylpentyloxymethoxycarbonyl group, 5-phenylpentyloxyethoxy Rubonyl group, 3- (5-phenylpentyloxy) propoxycarbonyl group, 4- (5-phenylpentyloxy) butoxycarbonyl group, 5- (5-phenylpentyloxy) pentyloxycarbonyl group, 6- (5-phenylpentyl group) Oxy) hexyloxycarbonyl group, 6-phenylhexyloxymethoxycarbonyl group, 6-phenylhexyloxyethoxycarbonyl group, 3- (6-phenylhexyloxy) propoxycarbonyl group, 4- (6-phenylhexyloxy) butoxycarbonyl group And 5- (6-phenylhexyloxy) pentyloxycarbonyl group, 6- (6-phenylhexyloxy) hexyloxycarbonyl group and the like.

  As C 2-6 alkenyloxycarbonyl group, for example, vinyloxycarbonyl group, 2-propenyloxycarbonyl group (common name: allyloxycarbonyl group), 2-buten-1-yloxycarbonyl group, 3-butene-1-yl Yloxycarbonyl group, 4-penten-1-yloxycarbonyl group, 3-penten-1-yloxycarbonyl group, 5-hexen-1-yloxycarbonyl group, 4-hexen-1-yloxycarbonyl group, 3 And -hexen-1-yloxycarbonyl group etc. can be mentioned.

  Examples of the C 2-6 alkynyloxycarbonyl group include an acetyleneoxycarbonyl group, a 2-propynyloxycarbonyl group, a 2-butyn-1-yloxycarbonyl group, a 3-butyn-1-yloxycarbonyl group, and a 4-pentyne- 1-yloxycarbonyl group, 3-pentyn-1-yloxycarbonyl group, 5-hexyn-1-yloxycarbonyl group, 4-hexyn-1-yloxycarbonyl group, 3-hexyn-1-yloxycarbonyl group Etc. can be mentioned.

  As a C3-8 cycloalkyl substituted C1-6 alkoxycarbonyl group, for example, cyclopropyl methoxycarbonyl group, cyclobutyl methoxy carbonyl group, cyclopentyl methoxy carbonyl group, cyclohexyl methoxy carbonyl group, cycloheptyl methoxy carbonyl group, cyclooctyl methoxy carbonyl group , 2-cyclopropylethoxycarbonyl group, 2-cyclobutylethoxycarbonyl group, 2-cyclopentylethoxycarbonyl group, 2-cyclohexylethoxycarbonyl group, 2-cycloheptylethoxycarbonyl group, 3-cyclopropylpropoxycarbonyl group, 3-cyclo Butylpropoxycarbonyl group, 3-cyclopentylpropoxycarbonyl group, 3-cyclohexylpropoxycarbonyl group, 3-cycloheptene group L-propoxycarbonyl group, 3-cyclooctylpropoxycarbonyl group, 4-cyclopropylbutoxycarbonyl group, 4-cyclobutylbutoxycarbonyl group, 4-cyclohexylbutoxycarbonyl group, 5-cyclohexylpentyloxycarbonyl group, 6-cyclohexylhexyloxycarbonyl And the like.

  Examples of benzoyl-substituted C1-6 alkoxycarbonyl group include benzoylmethoxycarbonyl group, 2-benzoylethoxycarbonyl group, 1-benzoylethoxycarbonyl group, 3- (benzoyl) propoxycarbonyl group, 4- (benzoyl) butoxycarbonyl group, Examples include 5- (benzoyl) pentyloxycarbonyl group, 6- (benzoyl) hexyloxycarbonyl group and the like.

  A phenoxy group (in which at least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group is substituted on a phenyl ring For example, phenoxy group, 2-fluorophenoxy group, 3-fluorophenoxy group, 4-fluorophenoxy group, 2-chlorophenoxy group, 3-chlorophenoxy group, 4-chlorophenoxy group, 2) -Bromophenoxy group, 3-bromophenoxy group, 4-bromophenoxy group, 2-iodophenoxy group, 3-iodophenoxy group, 4-iodophenoxy group, 2,3-difluorophenoxy group, 3,4-difluorophenoxy group , 3,5-difluorophenoxy group, 2,4-difluorophenoxy group, 2, 6 Difluorophenoxy group, 2,3-dichlorophenoxy group, 3,4-dichlorophenoxy group, 3,5-dichlorophenoxy group, 2,4-dichlorophenoxy group, 2,6-dichlorophenoxy group, 2,3,4- Trifluorophenoxy group, 3,4,5-trifluorophenoxy group, 3,4,5-trichlorophenoxy group, 2,4,6-trifluorophenoxy group, 2,3,4,5,6-pentafluorophenoxy Group, 2,4,6-trichlorophenoxy group, 2-fluoro-4-chlorophenoxy group, 2-fluoro-4-bromophenoxy group, 3-fluoro-4-chlorophenoxy group, 2-methylphenoxy group, 3- Methylphenoxy group, 4-methylphenoxy group, 2,6-dimethylphenoxy group, 2,4,6-trimethylphenoxy group, 2- Ethyl 3-chlorophenoxy group, 3-methyl-4-chlorophenoxy group, 2-chloro-4-methylphenoxy group, 2-methyl-3-fluorophenoxy group, 2-trifluoromethylphenoxy group, 3-trifluoro Methyl phenoxy group, 4-trifluoromethyl phenoxy group, 3,5-di (trifluoromethyl) phenoxy group, 3,4- di (trifluoromethyl) phenoxy group, 2,4- di (trifluoromethyl) phenoxy group , 2-pentafluoroethyl phenoxy group, 3-pentafluoroethyl phenoxy group, 4-pentafluoroethyl phenoxy group, 2-isopropyl phenoxy group, 3-isopropyl phenoxy group, 4-isopropyl phenoxy group, 2-tert-butyl phenoxy group , 3-tert-butylphenoxy group, 4-te rt-Butylphenoxy group, 2-sec-butylphenoxy group, 3-sec-butylphenoxy group, 4-sec-butylphenoxy group, 4-n-butylphenoxy group, 4-n-pentylphenoxy group, 4-n- Hexylphenoxy, 2-n-heptafluoropropylphenoxy, 3-n-heptafluoropropylphenoxy, 4-n-heptafluoropropylphenoxy, 4-pentylphenoxy, 4-hexylphenoxy, 2-methoxyphenoxy Group, 3-methoxyphenoxy group, 4-methoxyphenoxy group, 2-methoxy-3-chlorophenoxy group, 2-fluoro-3-methoxyphenoxy group, 2-fluoro-4-methoxyphenoxy group, 2-fluoro-4- 4- Bromophenoxy group, 4-chloro-3-fluorophenoxy group, , 3,4-trichlorophenoxy group, 3,4,5-trifluorophenoxy group, 2,4,6-trichlorophenoxy group, 2,4-dimethylphenoxy group, 2,3-dimethylphenoxy group, 3,5- Dimethylphenoxy, 2,5-dimethylphenoxy, 4-isopropoxyphenoxy, 4-n-butoxyphenoxy, 2,4-dimethoxyphenoxy, 2,3-dimethoxyphenoxy, 3,5-dimethoxyphenoxy 2,5-Dimethoxyphenoxy, 2,4,6-trimethoxyphenoxy, 3,5-di (trifluoromethoxy) phenoxy, 3-chloro-4-methoxyphenoxy, 2-chloro-4-trichloro Fluoromethoxyphenoxy group, 3-methyl-4-fluorophenoxy group, 4-bromo-3-trifluoromethyl Phenoxy group, 2,6-dimethoxyphenoxy group, 2-trifluoromethoxyphenoxy group, 3-trifluoromethoxyphenoxy group, 4-trifluoromethoxyphenoxy group, 2,3-di (trifluoromethoxy) phenoxy group, 2, 4-di (trifluoromethoxy) phenoxy group, 2-pentafluoroethoxyphenoxy group, 3-pentafluoroethoxyphenoxy group, 4-pentafluoroethoxyphenoxy group, 2-isopropoxyphenoxy group, 3-isopropoxyphenoxy group, 4 -Isopropoxyphenoxy group, 2-tert-butoxyphenoxy group, 3-tert-butoxyphenoxy group, 4-tert-butoxyphenoxy group, 2-sec-butoxyphenoxy group, 3-sec-butoxyphenoxy group, 4-sec- Butoxy Phenoxy groups such as phenoxy group, 4-n-hexyloxyphenoxy group, 2-n-heptafluoropropoxyphenoxy group, 3-n-heptafluoropropoxyphenoxy group, 4-n-heptafluoropropoxyphenoxy group, etc. Is substituted by 1 to 5, preferably 1 to 3 groups selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group, and a halogen substituted or unsubstituted C1-6 alkoxy group May be Can be mentioned.

  8-azabicyclo [3,2,1] octyl group (8-azabicyclo [3,2,1] octane ring, at least one phenoxy group (phenyl ring, halogen atom, halogen substituted or unsubstituted At least one member selected from the group consisting of a C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted). For example, 8-azabicyclo [3,2,1] octane-8-yl group, 3-phenoxy-8-azabicyclo [3,2,1] octan-8-yl group, 3- (3-chlorophenoxy) -8 -Azabicyclo [3,2,1] octan-1-yl group, 3- (4-bromophenoxy) -8-azabicyclo [3,2,1] octan-8-yl group, 3- (2-fluorophenoxy) -8-Azabicyclo [3,2,1] octan-8-yl group, 3- (3-iodophenoxy) -8-azabicyclo [3,2,1] octan-8-yl group, 3- (3- tri- Fluoromethyl phenoxy) -8-azabicyclo [3,2,1] octan-1-yl group, 3- (3-methylphenoxy) -8-azabicyclo [3,2,1] octan-1-yl group, 3- (4-Methoxyphenoxy) -8-azabicyclo [3,2,1] octan-1-yl group, 3- (3,5-ditrifluoromethylphenoxy) -8-azabicyclo [3,2,1] octane-1 -Yl group, 3- (3-trifluoromethyl-4-fluorophenoxy) -8-azabicyclo [3,2,1] octan-1-yl group, 3- (2-trifluoromethoxy-3-chlorophenoxy) group -8- Xabicyclo [3,2,1] octan-1-yl group, 3- (2,4-difluorophenoxy) -8-azabicyclo [3,2,1] octan-1-yl group, 3- (2,4,4 6-Trichlorophenoxy) -8-azabicyclo [3,2,1] octan-1-yl group, 3- (4-trifluoromethylphenoxy) -8-azabicyclo [3,2,1] octan-1-yl group , 3- (3-trifluoromethoxyphenoxy) -8-azabicyclo [3,2,1] octan-1-yl group, 3- (4-trifluoromethoxyphenoxy) -8-azabicyclo [3,2,1] 8-azabicyclo [3,2,1] octyl groups such as octan-1-yl group (as a substituent, phenoxy group (on phenyl ring, halogen on phenyl ring) (8-azabicyclo [3,2,1] octane ring atom, One to five, preferably one to three groups selected from the group consisting of a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted. ) May be substituted at least one kind. Can be mentioned.

  As a pyridyl group [in pyridine ring, at least one halogen-substituted or unsubstituted C1-6 alkyl group may be substituted as a substituent], for example, pyridin-3-yl group, pyridine-2- , Pyridin-4-yl group, 4-trifluoromethylpyridin-2-yl group, 4-trifluoromethylpyridin-3-yl group, 5-trifluoromethylpyridin-2-yl group, 5-trifluoro Methylpyridin-3-yl group, 2-trifluoromethylpyridin-3-yl group, 2,4-dimethylpyridin-3-yl group, 3,4,5-trimethylpyridin-2-yl group, 4-ethylpyridine Pyridyl groups such as 2-yl group, 3-n-butylpyridin-2-yl group, 5-n-pentylpyridin-2-yl group, 4-n-hexylpyridin-2-yl group and the like On the pyridine ring, and a halogen substituted or unsubstituted C1~6 alkyl group may be also be one to three substituents) as a substituent.

A 5- to 7-membered saturated heterocyclic ring formed by bonding R ⁴⁷ and R ⁴⁸ together with adjacent nitrogen atoms with or without other heteroatoms (at least one substituent as a substituent on the heterocyclic ring) [Phenyl ring substituted by at least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group, and a halogen-substituted or unsubstituted C1-6 alkoxy group] And the like] may be substituted), for example, pyrrolidinyl group, morpholino group, thiomorpholino group, piperazyl group, piperidyl group, homopiperazyl group, 4-phenylpiperazin-1-yl group, 4 -Phenylpiperidin-1-yl group, 4- (3-chlorophenyl) piperazin-1-yl group, 4- (4-chlorophenyl) piperazine-1 -Yl, 4- (3,4-dichlorophenyl) piperazin-1-yl, 4- (3-trifluoromethylphenyl) piperazin-1-yl, 4- (4-trifluoromethylphenyl) piperazine-1-one -Yl, 4- (3-trifluoromethoxyphenyl) piperazin-1-yl, 4- (4-trifluoromethoxyphenyl) piperazin-1-yl, 4-phenylpiperidin-1-yl, 4- (4- 3-chlorophenyl) piperidin-1-yl group, 4- (4-chlorophenyl) piperidin-1-yl group, 4- (3,4-dichlorophenyl) piperidin-1-yl group, 4- (3-trifluoromethylphenyl) ) Piperidin-1-yl group, 4- (4-trifluoromethylphenyl) piperidin-1-yl group, 4- (3-trifluoromethoxy) Nyl) piperidin-1-yl group, 4- (4-trifluoromethoxyphenyl) piperidin-1-yl group, 4- (2,4,6-trifluorophenyl) piperazin-1-yl group, 4- (4 -Methylphenyl) piperazin-1-yl group, 4- (3-methoxyphenyl) piperazin-1-yl group, 4- (3,4-dimethoxylophenyl) piperazin-1-yl group, 4- (2,4 (2,4) -Dimethylphenyl) piperazin-1-yl group, 4- (2,4,6-trimethoxyphenyl) piperazin-1-yl group, 4- (3,4,5-trimethylphenyl) piperazin-1-yl group, 4- (2,4,6-trifluorophenyl) piperidin-1-yl group, 4- (2,3,4,5,6-pentafluorophenyl) piperidin-1-yl group, 4- (4-methyl) Phenyl) Piperidin-1-yl group, 4- (3-methoxyphenyl) piperidin-1-yl group, 4- (3,4-dimethoxylophenyl) piperidin-1-yl group, 4- (2,4-dimethylphenyl) Piperidin-1-yl group, 4- (2,4,6-trimethoxyphenyl) piperidin-1-yl group, 4- (3,4,5-trimethylphenyl) piperidin-1-yl group, 3- (4 -Methylphenyl) morpholino group, 3- (3-methoxyphenyl) pyrrolidinyl-1-yl group, 2- (4-methylphenyl) pyrrolidinyl-1-yl group, 4- (2,4,6-trimethoxyphenyl) group Homopiperazin-1-yl group, 4- (3,4,5-trimethylphenyl) thiomorpholino group, 2,4-diphenylpiperazin-1-yl group, 2,4,6-triphenylpiperazine- -Yl group, 4-phenylpiperazin-1-yl group, 4-phenylpiperidin-1-yl group, 3- (3-chlorophenyl) pyrrolidin-1-yl group, 3- (4-chlorophenyl) morpholino group, 4- (3,4-dichlorophenyl) homopiperazin-1-yl group, 3- (3-trifluoromethylphenyl) thiomorpholino group, 2- (4-trifluoromethylphenyl) pyrrolidin-1-yl group, 2- (3 -Trifluoromethoxyphenyl) morpholino group, 3- (4-trifluoromethoxyphenyl) homopiperazin-1-yl group, 3-phenylpyrrolidin-1-yl group, 4- (3-chlorophenyl) morpholino group, 4- (4- (3-chlorophenyl) morpholino group 4-chlorophenyl) homopiperidin-1-yl group, 3- (3,4-dichlorophenyl) thiomorpholino group, 3- (3-t) As a substituent on a heterocycle such as fluoromethylphenyl) pyrrolidin-1-yl group, 4- (4-trifluoromethylphenyl) homopiperazin-1-yl group, 3-phenylthiomorpholino group, 4-phenylmorpholino group, etc. Phenyl group (on the phenyl ring, 1 to 5 groups selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group, preferably One to three may be substituted. And the above-mentioned heterocycles which may be substituted by 1 to 3).

  A phenyl C1-6 alkoxy group (wherein at least one of the groups selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group on the phenyl ring And the species may be substituted) is a group selected from the group consisting of a halogen atom as defined above, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group Is a phenylC1-6 alkoxy group which may be substituted by 1 to 5, preferably 1 to 3 groups, and examples thereof include a benzyloxy group, a 2-phenylethoxy group, a 3-phenylpropoxy group and a 2-phenylpropoxy group. Group, 4-phenyl butoxy group, 5-phenyl pentoxy group, 4-phenyl pentoxy group, 6-phenylhexylo , 2-fluorobenzyloxy, 3-fluorobenzyloxy, 4-fluorobenzyloxy, 2- (2-fluorophenyl) ethoxy, 2- (3-fluorophenyl) ethoxy, 2- (4) -Fluorophenyl) ethoxy group, 2-chlorobenzyloxy group, 3-chlorobenzyloxy group, 4-chlorobenzyloxy group, 2-fluoro-4-bromobenzyloxy group, 4-chloro-3-fluorobenzyloxy group, 2,3,4-trichlorobenzyloxy group, 3,4,5-trifluorobenzyloxy group, 2,3,4,5,6-pentafluorobenzyloxy group, 2,4,6-trichlorobenzyloxy group, 4-isopropylbenzyloxy group, 4-n-butylbenzyloxy group, 4-methylbenzyloxy group, 2-methyl ben Dihydroxy, 3-methylbenzyloxy, 2,4-dimethylbenzyloxy, 2,3-dimethylbenzyloxy, 2,6-dimethylbenzyloxy, 3,5-dimethylbenzyloxy, 2,5- Dimethyl benzyloxy group, 2,4,6-trimethylbenzyloxy group, 3,5-ditrifluoromethylbenzyloxy group, 4-isopropoxybenzyloxy group, 4-n-butoxybenzyloxy group, 4-methoxybenzyloxy group , 2-methoxybenzyloxy group, 3-methoxybenzyloxy group, 2,4-dimethoxybenzyloxy group, 2,3-dimethoxybenzyloxy group, 2,6-dimethoxybenzyloxy group, 3,5-dimethoxybenzyloxy group 2,5-Dimethoxybenzyloxy group 2,4,6-trimethoxyben Dihydroxy group, 3,5-ditrifluoromethoxybenzyloxy group, 2-isopropoxybenzyloxy group, 3-chloro-4-methoxybenzyloxy group, 2-chloro-4-trifluoromethoxybenzyloxy group, 3-methyl- 4-fluorobenzyloxy group, 4-bromo-3-trifluoromethylbenzyloxy group, 2- (2-chlorophenyl) ethoxy group, 2- (3-chlorophenyl) ethoxy group, 2- (4-chlorophenyl) ethoxy group, 2-trifluoromethylbenzyloxy group, 3-trifluoromethylbenzyloxy group, 4-trifluoromethylbenzyloxy group, 2-trifluoromethoxybenzyloxy group, 3-trifluoromethoxybenzyloxy group, 4-trifluoromethoxy Benzyloxy group, 2- (2-trifluoro) Ethylphenyl) ethoxy group, 2- (3-trifluoromethylphenyl) ethoxy group, 2- (4-trifluoromethylphenyl) ethoxy group, 2- (2-trifluoromethoxyphenyl) ethoxy group, 2- (3-triol) Fluoromethoxyphenyl) ethoxy group, 2- (4-trifluoromethoxyphenyl) ethoxy group, 3- (2-trifluoromethylphenyl) propoxy group, 3- (3-trifluoromethylphenyl) propoxy group, 3- (4 -Trifluoromethylphenyl) propoxy group, 3- (2-trifluoromethylphenyl) propoxy group, 3- (3-trifluoromethoxyphenyl) propoxy group, 3- (4-trifluoromethoxyphenyl) propoxy group, 4- (4-trifluoromethoxyphenyl) propoxy group (3-trifluoromethylphenyl) butoxy group, 5- (4-trif Omethylphenyl) pentoxy group, 4- (4-trifluoromethylphenyl) pentoxy group, 4- (4-trifluoromethoxyphenyl) pentoxy group, 6- (3-trifluoromethylphenyl) hexyloxy group, 6- (6 Examples include 4-trifluoromethylphenyl) hexyloxy group, 6- (4-trifluoromethoxyphenyl) hexyloxy group and the like.

  An amino-substituted C2-6 alkenyl group (wherein the amino group includes a C1-6 alkyl group and a phenyl group [wherein a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1 -6 alkoxy group, at least one group may be substituted with at least one group selected from the group consisting of at least one group selected from the group consisting of Group, 3-amino-2-propenyl group, 3-amino-1-propenyl group, 4-amino-3-butenyl group, 4-amino-3-butenyl group, 5-amino-4-pentenyl group, 6-amino -5-hexenyl group, methylaminovinyl group, 3-methylamino-2-propenyl group, 3-methylamino-1-propenyl group, 4-methylamino-3-butenyl group Group, 4-methylamino-3-butenyl group, 5-methylamino-4-pentenyl group, 6-methylamino-5-hexenyl group, methylaminovinyl group, 3-methylamino-2-propenyl group, 3-dimethyl Amino-2-propenyl group, 3-ethylamino-1-propenyl group, 3-diethylamino-1-propenyl group, 4-ethylamino-3-butenyl group, 4-dimethylamino-3-butenyl group, 4-diethylamino- 3-butenyl group, 5-ethylamino-4-pentenyl group, 6-ethylamino-5-hexenyl group, n-propylaminovinyl group, 3-n-propylamino-2-propenyl group, 3-n-propylamino -1-propenyl group, 4-n-propylamino-3-butenyl group, 4-n-propylamino-3-butenyl group, 5-n-propynyl group Amino-4-pentenyl group, 6-n-propylamino-5-hexenyl group, n-butylaminovinyl group, 3-n-butylamino-2-propenyl group, 3-n-butylamino-1-propenyl group, 4-n-butylamino-3-butenyl group, 4-n-butylamino-3-butenyl group, 5-n-butylamino-4-pentenyl group, 6-n-butylamino-5-hexenyl group, n- Pentylaminovinyl group, 3-n-pentylamino-2-propenyl group, 3-n-hexylamino-1-propenyl group, 4-n-hexylamino-3-butenyl group, 4-n-hexylamino-3- Butenyl group, 5-n-hexylamino-4-pentenyl group, 6-n-pentylamino-5-hexenyl group, phenylaminovinyl group, 3-phenylamino-2-propenyl group , 3-phenylamino-1-propenyl group, 4-phenylamino-3-butenyl group, 4-phenylamino-3-butenyl group, 5-phenylamino-4-pentenyl group, 6-phenylamino-5-hexenyl group 4-chlorophenylaminovinyl group, 3- (4-bromophenyl) amino-2-propenyl group, 3- (2,4-dichlorophenyl) amino-1-propenyl group, 4- (2,4,6-trichlorophenyl) ) Amino-3-butenyl group, 4- (2,3,4,5,6-pentafluorophenyl) amino-3-butenyl group, 4- (4-fluorophenyl) amino-3-butenyl group, 5- ( 4-iodophenyl) amino-4-pentenyl group, 6- (4-chlorophenyl) amino-5-hexenyl group, (3-methylphenyl) aminovinyl group, (4 Trifluoromethylphenyl) aminovinyl group, 3- (4-trifluoromethylphenyl) amino-2-propenyl group, 3- (4-trifluoromethylphenyl) amino-1-propenyl group, 4- (4-trifluoro) Methylphenyl) amino-3-butenyl group 4- (4-trifluoromethylphenyl) amino-3-butenyl group 5- (3,4-dimethylphenyl) amino-4-pentenyl group 6- (3,4 5-trimethylphenyl) amino-5-hexenyl group, (2-methoxyphenyl) aminovinyl group, (4-trifluoromethoxyphenyl) aminovinyl group, 3- (4-trifluoromethoxyphenyl) amino-2-propenyl Group, 3- (3,5-dimethoxyphenyl) amino-1-propenyl group, 4- (2,5-dimethoxypheny) L) amino-3-butenyl group, 4- (2,4,6-trimethoxyphenyl) amino-3-butenyl group, 5- [N-methyl-N- (4-trifluoromethylphenyl) amino] -4 An amino-substituted C2-6 alkenyl group such as a pentenyl group, 6- [N-ethyl-N- (4-trifluoromethoxyphenyl) amino] -5-hexenyl group (wherein the amino group is a C1-6 alkyl group and Phenyl group [in the phenyl ring, 1 to 5 groups selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group, preferably One to three may be substituted. One to two groups selected from the group consisting of Can be mentioned.

  Examples of the oxazolidinyl group (at least one oxo group may be substituted on the oxazolidine ring) include, for example, oxazolidin-4-yl group, oxazolidin-5-yl group, 2-oxooxazolidin-4-yl group. And 2-oxo-oxazolidin-5-yl group.

A phenyl C1-6 alkyl group (a phenoxy group on the phenyl ring [a group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group on the phenyl ring At least one member selected from the group consisting of: a halogen atom; a halogen substituted or unsubstituted C.sub.1-6 alkyl group; a halogen substituted or unsubstituted C.sub.1-6 alkoxy group; an amino group (amino group [C1-6 alkyl group and phenyl C1-6 alkyl group [on the phenyl ring, consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group At least one group selected from the group consisting of at least one group selected from the group consisting of Species may be substituted); piperazinyl group [in the piperazine ring at least one phenyl C.sub.1-6 alkyl group (on the phenyl ring a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and At least one of a group selected from the group consisting of a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted) and a piperidyl group [on the piperidine ring, at least One amino group may be substituted. On the amino group, a phenyl group (on the phenyl ring, a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group) At least one group selected from the group consisting of at least one group optionally substituted) and a C1-6 alkyl group may be substituted. As at least one kind of group selected from the group consisting of may be substituted), for example, benzyl group, 1-phenethyl group, 2-phenethyl group, 3-phenylpropyl group, 2-phenylpropyl group, 4-phenylbutyl group, 5-phenylpentyl group, 4-phenylpentyl group, 6-phenylhexyl group, 2-fluorobenzyl group, 3-fluorobenzyl group, 4-fluorobenzyl group, 2-chlorobenzyl group, 3- Chlorobenzyl, 4-chlorobenzyl, 2-bromobenzyl, 3-bromobenzyl, 4-bromobenzyl, 2-iodobenzyl, 3-iodobenzyl, 4-iodobenzyl, 2,3- Difluorobenzyl group, 3,4-difluorobenzyl group, 3,5-difluorobenzyl group, 2,3,4,5,6-pentafluoroben Group, 2,4-difluorobenzyl group, 2,6-difluorobenzyl group, 2,3-dichlorobenzyl group, 3,4-dichlorobenzyl group, 3,5-dichlorobenzyl group, 2,4-dichlorobenzyl group 2,6-dichlorobenzyl group, 2-fluoro-4-bromobenzyl group, 4-chloro-3-fluorobenzyl group, 2,3,4-trichlorobenzyl group, 3,4,5-trifluorobenzyl group, 2,4,6-trichlorobenzyl group, 4-isopropylbenzyl group, 4-n-butylbenzyl group, 4-methylbenzyl group, 2-methylbenzyl group, 3-methylbenzyl group, 2,4-dimethylbenzyl group, 2,3-Dimethylbenzyl, 2,6-dimethylbenzyl, 3,5-dimethylbenzyl, 2,5-dimethylbenzyl, 2,4,6-trimethyl Ndidyl group, 3,5-ditrifluoromethylbenzyl group, 2,3,4,5,6-pentafluorobenzyl group, 4-isopropoxybenzyl group, 4-n-butoxybenzyl group, 4-methoxybenzyl group, 2 -Methoxybenzyl group, 3-methoxybenzyl group, 2,4-dimethoxybenzyl group, 2,3-dimethoxybenzyl group, 2,6-dimethoxybenzyl group, 3,5-dimethoxybenzyl group, 2,5-dimethoxybenzyl group 2,4,6-Trimethoxybenzyl group, 3,5-ditrifluoromethoxybenzyl group, 2-isopropoxybenzyl group, 3-chloro-4-methoxybenzyl group, 2-chloro-4-trifluoromethoxybenzyl group , 3-methyl-4-fluorobenzyl group, 4-bromo-3-trifluoromethylbenzyl group, 2-trifluoro Methyl benzyl group, 3-trifluoromethylbenzyl group, 4-trifluoromethylbenzyl group, 2-pentafluoroethyl benzyl group, 3-pentafluoroethyl benzyl group, 4-pentafluoroethyl benzyl group, 2-trifluoromethoxybenzyl Group, 3-trifluoromethoxybenzyl group, 4-trifluoromethoxybenzyl group, 2-pentafluoroethoxybenzyl group, 3-pentafluoroethoxybenzyl group, 4-pentafluoroethoxybenzyl group, 2- (2-trifluoromethyl) Phenyl) ethyl group, 2- (3-trifluoromethylphenyl) ethyl group, 2- (4-trifluoromethylphenyl) ethyl group, 2- (2-trifluoromethoxyphenyl) ethyl group, 2- (3-triphenyl) ethyl group Fluoromethoxyphenyl) ethyl group, 2- ( -Trifluoromethoxyphenyl) ethyl group, 2- (2-pentafluoroethoxyphenyl) ethyl group, 2- (3-pentafluoroethoxyphenyl) ethyl group, 2- (4-pentafluoroethoxyphenyl) ethyl group, 3- (2-trifluoromethylphenyl) propyl group, 3- (3-trifluoromethylphenyl) propyl group, 3- (4-trifluoromethylphenyl) propyl group, 3- (2-trifluoromethoxyphenyl) propyl group, 3- (3-trifluoromethoxyphenyl) propyl group, 3- (4-trifluoromethoxyphenyl) propyl group, 3- (3-pentafluoroethoxyphenyl) propyl group, 3- (4-pentafluoroethoxyphenyl) propyl group Group, 4- (3-pentafluoroethoxyphenyl) butyl group, -(4-trifluoromethylphenyl) pentyl group, 4- (4-trifluoromethylphenyl) pentyl group, 4- (4-trifluoromethoxyphenyl) pentyl group, 6- (3-trifluoromethylphenyl) hexyl group , 6- (4-trifluoromethylphenyl) hexyl group, 6- (4-trifluoromethoxyphenyl) hexyl group, 2-aminobenzyl group, 2,4-diaminobenzyl group, 2,4,6-triaminobenzyl Group, 2-methylaminobenzyl group, 2-benzylaminobenzyl group, 2-fluorobenzylaminobenzyl group, 3-fluorobenzylaminobenzyl group, 4-fluorobenzylaminobenzyl group, 2-chlorobenzyl group, 3-chlorobenzyl Aminobenzyl group, 4-chlorobenzylaminobenzyl group, 2-bromobenzene Dylaminobenzyl group, 3-bromobenzylaminobenzyl group, 4-bromobenzylaminobenzyl group, 2-iodobenzylaminobenzyl group, 3-iodobenzylaminobenzyl group, 4-iodobenzylaminobenzyl group, 2,3-difluoro Benzylaminobenzyl group, 3,4-difluorobenzylaminobenzyl group, 3,5-difluorobenzylaminobenzyl group, 2,3,4,5,6-pentafluorobenzylaminobenzyl group, 2,4-difluorobenzylaminobenzyl group Group, 2,6-difluorobenzylaminobenzyl group, 2,3-dichlorobenzylaminobenzyl group, 3,4-dichlorobenzylaminobenzyl group, 3,5-dichlorobenzylaminobenzyl group, 2,4-dichlorobenzylaminobenzyl group Group 2,6-dichloro N-benzylaminobenzyl group, 2-fluoro-4-bromobenzylaminobenzyl group, 4-chloro-3-fluorobenzylaminobenzyl group, 2,3,4-trichlorobenzylaminobenzyl group, 3,4,5-trifluoro Benzylaminobenzyl group, 2,4,6-trichlorobenzylaminobenzyl group, 4-isopropylbenzylaminobenzyl group, 4-n-butylbenzylaminobenzyl group, 4-methylbenzylaminobenzyl group, 2-methylbenzylaminobenzyl group , 3-methylbenzylaminobenzyl group, 2,4-dimethylbenzylaminobenzyl group, 2,3-dimethylbenzylaminobenzyl group, 2,6-dimethylbenzylaminobenzyl group, 3,5-dimethylbenzylaminobenzyl group, 2 3,5-Dimethylbenzylaminobenzyl , 2,4,6-trimethylbenzylaminobenzyl, 3,5-ditrifluoromethylbenzylaminobenzyl, 2,3,4,5,6-pentafluorobenzylaminobenzyl, 4-isopropoxybenzylaminobenzyl Group, 4-n-butoxybenzylaminobenzyl group, 4-methoxybenzylaminobenzyl group, 2-methoxybenzylaminobenzyl group, 3-methoxybenzylaminobenzyl group, 2,4-dimethoxybenzylaminobenzyl group, 2,3- Dimethoxybenzylaminobenzyl, 2,6-dimethoxybenzylaminobenzyl, 3,5-dimethoxybenzylaminobenzyl, 2,5-dimethoxybenzylaminobenzyl, 2,4,6-trimethoxybenzylaminobenzyl, 3 5-Ditrifluoromethoxy Benzylaminobenzyl, 2-isopropoxybenzylaminobenzyl, 3-chloro-4-methoxybenzylaminobenzyl, 2-chloro-4-trifluoromethoxybenzylaminobenzyl, 3-methyl-4-fluorobenzylaminobenzyl Group, 4-bromo-3-trifluoromethylbenzylaminobenzyl group, 2-trifluoromethylbenzyl group, aminobenzyl group, 3-trifluoromethylbenzylaminobenzyl group, 4-trifluoromethylbenzylaminobenzyl group, 2- Pentafluoroethoxybenzylaminobenzyl group, 3-pentafluoroethoxybenzylaminobenzyl group, 4-pentafluoroethoxybenzylaminobenzyl group, 2-trifluoromethoxybenzylaminobenzyl group, 3-trifluorometh 3-benzylaminobenzyl, 4-trifluoromethoxybenzylaminobenzyl, 2-pentafluoroethoxybenzylaminobenzyl, 3-pentafluoroethoxybenzylaminobenzyl, 4-pentafluoroethoxybenzylaminobenzyl, 3- (N -Methyl-N-benzylamino) benzyl group, 4- (dibenzylamino) benzyl group, 2-dimethylaminobenzyl group, 3-dimethylaminobenzyl group, 4-dimethylaminobenzyl group, 2- (2-dimethylaminophenyl group) ) Ethyl group, 2- (3-dimethylaminophenyl) ethyl group, 2- (4-dimethylaminophenyl) ethyl group, 3- (2-dimethylaminophenyl) propyl group, 3- (3-dimethylaminophenyl) propyl Group, 3- (4-dimethylaminopheny) ) Propyl, 2-phenoxybenzyl, 2,3-diphenoxybenzyl, 2,4,6-tolyphenoxybenzyl, 2- (2-fluorophenoxy) benzyl, 3- (3-fluorophenoxy) benzyl Group, 4- (4-fluorophenoxy) benzyl group, 2- (2-chlorophenoxy) benzyl group, 3- (3-chlorophenoxy) benzyl group, 4- (4-chlorophenoxy) benzyl group, 2- (2) -Bromophenoxy) benzyl group, 3- (3-bromophenoxy) benzyl group, 4- (4-bromophenoxy) benzyl group, 2- (2-iodophenoxy) benzyl group, 3- (3-iodophenoxy) cybenzyl group , 4- (4-iodo-phenoxy) benzyl group, 3- (2,3-difluorophenoxy) benzyl group, 4- (3,4-diphenyl) Fluorophenoxy) benzyl group, 2- (3,5-difluorophenoxy) benzyl group, 4- (2,3,4,5,6-pentafluorophenoxy) benzyl group, 2- (2,4-difluorophenoxy) group Benzyl, 4- (2,6-difluorophenoxy) benzyl, 3- (2,3-dichlorophenoxy) benzyl, 2- (3,4-dichlorophenoxy) benzyl, 4- (3,5-dichloro) Phenoxy) benzyl group, 3- (2,4-dichlorophenoxy) benzyl group, 4- (2,6-dichlorophenoxy) benzyl group, 4- (2-fluoro-4-bromophenoxy) benzyl group, 3- (4) -Chloro-3-fluorophenoxy) benzyl group, 4- (2,3,4-trichlorophenoxy) benzyl group, 4- (3,4,5-trifluorophenoxy) ) Benzyl group, 4- (2,4,6-trichlorophenoxy) benzyl group, 2- (4-isopropylphenoxy) benzyl group, 3- (4-n-butylphenoxy) benzyl group, 4- (4-methylphenoxy) ) Benzyl group, 3


-(2-Methylphenoxy) benzyl group, 2- (3-methylphenoxy) benzyl group, 2- (2,4-dimethylphenoxy) benzyl group, 3- (2,3-dimethylphenoxy) benzyl group, 4- ( 2,6-Dimethylphenoxy) benzyl group, 2- (3,5-dimethylphenoxy) benzyl group, 3- (2,5-dimethylphenoxy) benzyl group, 2- (2,4,6-trimethylphenoxy) benzyl group 3- (3,5-ditrifluoromethylphenoxy) benzyl group, 4- (2,3,4,5,6-pentafluorophenoxy) benzyl group, 2- (4-isopropoxyphenoxy) benzyl group, 2- (4-n-butoxy phenoxy) benzyl group, 2- (4- methoxy phenoxy) benzyl group, 3- (2- methoxy phenoxy) benzyl group, 4- ( -Methoxyphenoxy) benzyl group, 2- (2,4-dimethoxyphenoxy) benzyl group, 3- (2,3-dimethoxyphenoxy) benzyl group, 4- (2,6-dimethoxyphenoxy) benzyl group, 2- (3 5-Dimethoxyphenoxy) benzyl group, 3- (2,5-dimethoxyphenoxy) benzyl group, 4- (2,4,6-trimethoxyphenoxy) benzyl group, 2- (3,5-ditrifluoromethoxyphenoxy) group Benzyl group, 3- (2-isopropoxyphenoxy) benzyl group, 4- (3-chloro-4-methoxyphenoxy) benzyl group, 3- (2-chloro-4-trifluoromethoxyphenoxy) benzyl group, 2- (2- 3-Methyl-4-fluorophenoxy) benzyl group, 3- (4-bromo-3-trifluoromethylphenoxy) bee Dyl, 4- (2-trifluoromethylphenoxy) benzyl, 2- (3-trifluoromethylphenoxy) benzyl, 3- (4-trifluoromethylphenoxy) benzyl, 4- (2-pentafluoroethoxy) Phenoxy) benzyl group, 2- (3-pentafluoroethoxyphenoxy) benzyl group, 3- (4-pentafluoroethoxyphenoxy) benzyl group, 4- (2-trifluoromethoxyphenoxy) benzyl group, 2- (3-trimethoxy group) Fluoromethoxyphenoxy) benzyl group, 3- (4-trifluoromethoxyphenoxy) benzyl group, 4- (2-pentafluoroethoxyphenoxy) benzyl group, 2- (3-pentafluoroethoxyphenoxy) benzyl group, 3- (4 -Pentafluoroethoxyphenoxy) benzyl group, 2- [ 3- (2-trifluoromethylphenoxy) phenyl] ethyl group, 2- [3- (3-trifluoromethylphenoxy) phenyl] ethyl group, 2- [4- (4-trifluoromethylphenoxy) phenyl] ethyl group , 3- [4- (2-trifluoromethylphenoxy) phenyl] propyl group, 4- [3- (3-pentafluoroethoxyphenoxy) phenyl] butyl group, 5- [4- (4-trifluoromethylphenoxy) group Phenyl] pentyl group, 6- [2- (3-trifluoromethylphenoxy) phenyl] hexyl group, 4- (1-piperazinyl) benzyl group, 4- (1-piperidinyl) benzyl group, 4- (4-benzyl-) group 1-piperazinyl) benzyl group, 4- (4- (3-chlorobenzyl) -1-piperazinyl) benzyl group, 4- (4- (2,4-) Dimethylbenzyl) -1-piperazinyl) benzyl group, 4- (4- (2,4-dimethylbenzyl) -1-piperazinyl) benzyl group, 4- (2,4-dibenzyl-1-piperazinyl) benzyl group, 4- (2,4-dibenzyl-1-piperazinyl) benzyl group (2,3,4-tribenzyl-1-piperazinyl) benzyl group, 4- (4- (4-trifluoromethoxybenzyl) -1-piperazinyl) benzyl group, 4- (4-anilino-1-piperidinyl) benzyl group , 4- (4- (3-trifluoromethylbenzyl) -1-piperazinyl) benzyl group, 4- [4- (N-methylanilino) -1-piperidinyl] benzyl group, 4- [4- (N-methyl-) 3-chloroanilino) -1-piperidinyl] benzyl group, 4- [4- (2,4-dimethylanilino) -1-piperidinyl] benzyl group, 4- [4- (N) Methyl-2,4,6-trimethoxyanilino) -1-piperidinyl] benzyl group, 4- [4- (4-trifluoromethoxyanilino) -1-piperidinyl] benzyl group, 4- [4- (N) -Methyl-3-trifluoromethylanilino) -1-piperidinyl] benzyl group, 4- (3,4-dianilino-1-piperidinyl) benzyl group, 4- (3,4,5-trianilino-1-piperidinyl) Phenyl C 1 to 6 alkyl groups such as benzyl group (on the phenyl ring phenoxy group [on the phenyl ring, halogen atoms, halogen substituted or unsubstituted C 1 to 6 alkyl groups and halogen substituted or unsubstituted C 1 to 6 alkoxy Groups selected from the group consisting of groups may be substituted by 1 to 5, preferably 1 to 3 groups; halogen atoms; halogen substituted or unsubstituted C1-6 alkyl group; halogen-substituted or unsubstituted C1-6 alkoxy group; amino group (C1-6 alkyl group and phenyl C1-6 alkyl group on amino group [halogen atom on halogen ring, halogen, 1 to 5, preferably 1 to 3 groups selected from the group consisting of a group selected from the group consisting of a substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group Or a group selected from the group consisting of one or two groups may be substituted); piperazinyl group [as a substituent, a phenyl C.sub.1-6 alkyl group as a substituent (on a phenyl ring) And 1 to 5 groups selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group And preferably 1 to 3 substituents may be substituted 1 to 3) and a piperidyl group [1 to 3 amino groups may be substituted on the piperidine ring . On the amino group, a phenyl group (on the phenyl ring, a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group is One to two groups selected from the group consisting of 1 to 5, preferably 1 to 3) and a C1 to 6 alkyl group may be substituted. 1 to 5, preferably 1 to 3 groups selected from the group consisting of

  An amino C1-6 alkyl group (on the amino group, a C1-6 alkyl group, a C1-6 alkoxycarbonyl group and a phenyl group [on a phenyl ring, a halogen atom or a halogen substituted or unsubstituted C1-6 alkyl group As at least one group selected from the group consisting of at least one group selected from the group consisting of Aminoethyl group, 1-aminoethyl group, 3-aminopropyl group, 4-aminobutyl group, 5-aminopentyl group, 6-aminohexyl group, 2-methyl-3-aminopropyl group, 1,1-dimethyl- 2-aminoethyl group, 2- (methylamino) ethyl group, 3- (methylamino) propyl group, 4- (methylamino) butyl group, 5- (methylamino) penty Group, 6- (methylamino) hexyl group, 2- (N-methyl-N-methoxycarbonylamino) ethyl group, 3- (N-methyl-N-methoxycarbonylamino) propyl group, 4- (N-methyl- group) N-methoxycarbonylamino) butyl group, 5- (N-methyl-N-methoxycarbonylamino) pentyl group, 6- (N-methyl-N-methoxycarbonylamino) hexyl group, 2- (N-ethoxycarbonyl-N group -Methylamino)) ethyl group, 3- (N-ethoxycarbonyl-N-methylamino) propyl group, 4- (N-ethoxycarbonyl-N-methylamino) butyl group, 5- (N-ethoxycarbonyl-N- group Methylamino) pentyl group, 6- (N-ethoxycarbonyl-N-methylamino) hexyl group, 2- [N-methyl-N- (n-pro) Xycarbonylamino)] ethyl group, 3- [N-methyl-N- (n-propoxycarbonylamino)] propyl group, 4- [N-methyl-N- (N-propoxycarbonylamino)] butyl group, 5- [N-methyl-N- (n-propoxycarbonylamino)] pentyl group, 6- [N-methyl-N- (n-propoxycarbonylamino)] hexyl group, 2- [N- (tert-butoxycarbonyl)- N-methylamino] ethyl group, 3- [N- (tert-butoxycarbonyl) -N-methylamino] propyl group, 4- [N- (tert-butoxycarbonyl) -N-methylamino] butyl group, 5- [N- (tert-butoxycarbonyl) -N-methylamino] pentyl group, 6- [N- (tert-butoxycarbonyl) -N-methylamino] Hexyl group, 2- [N-methyl-N- (n-pentoxycarbonyl) amino] ethyl group, 2- [N-methyl-N- (n-hexyloxycarbonyl) amino] ethyl group, 2- (N- Methylanilino) ethyl group, 3- (N-methylanilino) propyl group, 4- (N-methylanilino) butyl group, 2- (N-methyl-4-chloroanilino) ethyl group, 3- (N-methyl-4-chloroanilino) group Propyl group, 4- (N-methyl-4-chloroanilino) butyl group, 2- (4-fluoro-N-methylanilino) ethyl group, 3- (4-fluoro-N-methylanilino) propyl group, 2- (3- (4-fluoro-N-methylanilino) propyl group Fluoro-N-methylanilino) ethyl group, 3- (3-fluoro-N-methylanilino) propyl group, 4- (3-fluoro-N-methylanilino) butyl group, 2- 2-fluoro-N-methylanilino) ethyl group, 3- (2-fluoro-N-methylanilino) propyl group, 4- (2-fluoro-N-methylanilino) butyl group, 2- (2-chloro-N-methylanilino) group Ethyl group, 3- (2-chloro-N-methylanilino) propyl group, 4- (2-chloro-N-methylanilino) butyl group, 2- (3-chloro-N-methylanilino) ethyl group, 3- (3- (3-chloro-N-methylanilino) ethyl group Chloro-N-methylanilino) propyl group, 4- (3-chloro-N-methylanilino) butyl group, 2- (4-trifluoromethyl-N-methylanilino) ethyl group, 2- (4-methylanilino) ethyl group, 2 -(3,5-ditrifluoromethyl-N-ethoxycarbonylanilino) ethyl group, 2- (3,5-ditrifluoromethyl-N-methyl anily) ) Ethyl group, 2- (2,4-dimethyl-N-methylanilino) ethyl group, 2- (3,5-dimethoxy-N-methylanilino) ethyl group, 2- (2,4,6-trimethylanilino) ethyl Group, 2- (3,4,5-trimethoxyanilino) ethyl group, 3- (4-trifluoromethyl-N-methylanilino) propyl group, 4- (4-trifluoromethyl-N-methylanilino) butyl group , 2- (3-trifluoromethyl-N-methylanilino) ethyl group, 3- (3-trifluoromethyl-N-methylanilino) propyl group, 2- (2-trifluoromethyl-N-methylanilino) ethyl group, 3 -(2-trifluoromethyl-N-methylanilino) propyl, 4- (2-trifluoromethyl-N-methylanilino) butyl, 2- (4-trifluoro Romethoxy-N-methylanilino) ethyl group, 3- (4-trifluoromethoxy-N-methylanilino) propyl group, 4- (4-trifluoromethoxy-N-methylanilino) butyl group, 2- (3-trifluoromethoxy- N-methylanilino) ethyl group, 3- (3-trifluoromethoxy-N-methylanilino) propyl group, 4- (3-trifluoromethoxy-N-methylanilino) butyl group, 2- (2-trifluoromethoxy-N- Methylanilino) ethyl group, 3- (2-trifluoromethoxy-N-methylanilino) propyl group, 4- (2-trifluoromethoxy-N-methylanilino) butyl group, 2- (4-methoxy-N-methylanilino) ethyl group , 3- (4-methoxy-N-methylanilino) propyl group, 4- (4-methoxy-) -Methylanilino) butyl group, 2- (3-methoxy-N-methylanilino) ethyl group, 3- (3-methoxy-N-methylanilino) propyl group, 4- (3-methoxy-N-methylanilino) butyl group, 2- (3-methoxy-N-methylanilino) butyl group Amino C1-6 alkyl groups (amino group such as (2-methoxy-N-methylanilino) ethyl group, 3- (2-methoxy-N-methylanilino) propyl group, 4- (2-methoxy-N-methylanilino) butyl group, etc. In the above, a C1-6 alkyl group, a C1-6 alkoxycarbonyl group and a phenyl group [on the phenyl ring, a group selected from the group consisting of halogen or halogen substituted or unsubstituted C1-6 alkyl group is selected And the group selected from the group consisting of 5 and preferably 1 to 3 may be substituted). Ru.

  A phenyl group (on a phenyl ring, a halogen atom, a phenoxy group [on a phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group, and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group; As at least one kind of the group selected from the group consisting of at least one kind of the selected group may be substituted] and a C1-6 alkoxycarbonyl group optionally substituted, for example, a phenyl group , 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 2-bromophenyl group, 3-bromophenyl group, 4-bromophenyl group Group, 2-iodophenyl group, 3-iodophenyl group, 4-iodophenyl group, 2,3-difluorophenyl group Group, 3,4-difluorophenyl group, 3,5-difluorophenyl group, 2,4-difluorophenyl group, 2,6-difluorophenyl group, 2,3-dichlorophenyl group, 3,4-dichlorophenyl group, 3 5-dichlorophenyl group, 2,4-dichlorophenyl group, 2,6-dichlorophenyl group, 2,3,4-trifluorophenyl group, 3,4,5-trifluorophenyl group, 3,4,5-trichlorophenyl group Group, 2,4,6-trifluorophenyl group, 2,3,4,5,6-pentafluorophenyl group, 2,4,6-trichlorophenyl group, 2-fluoro-4-chlorophenyl group, 2-fluoro -4-bromophenyl group, 3-fluoro-4-chlorophenyl group, 2-methoxycarbonylphenyl group, 3-methoxycarbonylphenyl group, -Methoxycarbonylphenyl group, 2,4-dimethoxycarbonylphenyl group, 2,4,6-trimethoxycarbonylphenyl group, 2-ethoxycarbonylphenyl group, 3-ethoxycarbonylphenyl group, 4-ethoxycarbonylphenyl group, 2- Propoxycarbonyl carbonyl group, 3-propoxycarbonyl phenyl group, 4-propoxycarbonyl phenyl group, 2-butoxycarbonyl phenyl group, 3-butoxycarbonyl phenyl group, 4-butoxycarbonyl phenyl group, 4-pentoxycarbonyl phenyl group, 4- Hexyloxycarbonylphenyl group, 2-phenoxyphenyl group, 3-phenoxyphenyl group, 4-phenoxyphenyl group, 2- (2-chlorophenoxy) phenyl group, 2- (3-chlorophenoxy) phenyl group, 2 -(4-chlorophenoxy) phenyl group, 3- (2-chlorophenoxy) phenyl group, 3- (3-chlorophenoxy) phenyl group, 3- (4-chlorophenoxy) phenyl group, 4- (2-chlorophenoxy) group ) Phenyl group, 4- (2,4-dichlorophenoxy) phenyl group, 4- (2,4,6-trichlorophenoxy) phenyl group, 4- (3-chlorophenoxy) phenyl group, 4- (4-chlorophenoxy) ) Phenyl group, 2- (2-trifluoromethylphenoxy) phenyl group, 2- (3-trifluoromethylphenoxy) phenyl group, 2- (4-trifluoromethylphenoxy) phenyl group, 3- (2-trifluoro) Methylphenoxy) phenyl group, 3- (2-methylphenoxy) phenyl group, 3- (2,4-dimethylphenoxy) phenyl group 3- (2,4,6-trimethylphenoxy) phenyl group, 3- (2-methoxyphenoxy) phenyl group, 3- (2,4-dimethoxyphenoxy) phenyl group, 3- (2,4,6-triyl group) Methoxyphenoxy) phenyl group, 2- (3,5-ditrifluoromethylphenoxy) phenyl group, 2- (3,5-ditrifluoromethoxyphenoxy) phenyl group, 3- (3-trifluoromethylphenoxy) phenyl group, 3 -(4-Trifluoromethylphenoxy) phenyl group, 4- (2-trifluoromethylphenoxy) phenyl group, 4- (3-trifluoromethylphenoxy) phenyl group, 4- (4-trifluoromethylphenoxy) phenyl group , 2- (2-trifluoromethoxyphenoxy) phenyl group, 2- (3-trifluoromethoxyphen) Xyl) phenyl group, 2- (4-trifluoromethoxyphenoxy) phenyl group, 3- (2-trifluoromethoxyphenoxy) phenyl group, 3- (3-trifluoromethoxyphenoxy) phenyl group, 3- (4-tri- Phenyl groups such as fluoromethoxyphenoxy) phenyl group, 4- (2-trifluoromethoxyphenoxy) phenyl group, 4- (3-trifluoromethoxyphenoxy) phenyl group, 4- (4-trifluoromethoxyphenoxy) phenyl group, etc. (On the phenyl ring, selected from the group consisting of a halogen atom, a phenoxy group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group 1 to 5, preferably 1 to 3 substituted groups may be substituted) and 1-5, preferably 1 to 3 groups selected from the group consisting of C1-6 alkoxycarbonyl groups may be mentioned.

  Phenyl C1-6 alkoxycarbonyl group (on the phenyl ring, at least a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group As 1 type may be substituted), for example, benzyloxycarbonyl group, 1-phenethyloxycarbonyl group, 2-phenethyloxycarbonyl group, 3-phenylpropoxycarbonyl group, 2-phenylpropoxycarbonyl group, 4 -Phenylbutoxycarbonyl group, 5-phenylpentyloxycarbonyl group, 4-phenylpentyloxycarbonyl group, 6-phenylhexyloxycarbonyl, 2-fluorobenzyloxycarbonyl group, 3-fluorobenzyloxycarbonyl group, 4-fluoro Benzyloxycarbonyl group, 2-chlorobenzyloxycarbonyl group, 3-chlorobenzyloxycarbonyl group, 4-chlorobenzyloxycarbonyl group, 2-bromobenzyloxycarbonyl group, 3-bromobenzyloxycarbonyl group, 4-bromobenzyloxy group Carbonyl group, 2-iodobenzyloxycarbonyl group, 3-iodobenzyloxycarbonyl group, 4-iodobenzyloxycarbonyl group, 2,3-difluorobenzyloxycarbonyl group, 3,4-difluorobenzyloxycarbonyl group, 3,5 -Difluorobenzyloxycarbonyl group, 2,4-difluorobenzyloxycarbonyl group, 2,6-difluorobenzyloxycarbonyl group, 2,4,6-trifluorobenzyloxycarbonyl group, 2,3,4, , 6-Pentafluorobenzyloxycarbonyl group, 3,4,5-trifluorobenzyloxycarbonyl group, 2,3-dichlorobenzyloxycarbonyl group, 3,4-dichlorobenzyloxycarbonyl group, 3,5-dichlorobenzyloxy group Carbonyl group, 2,4-dichlorobenzyloxycarbonyl group, 2,6-dichlorobenzyloxycarbonyl group, 2,4,6-trichlorobenzyloxycarbonyl group, 3,4,5-trichlorobenzyloxycarbonyl group, perfluorobenzyl Oxycarbonyl group, 2-difluoromethylbenzyloxycarbonyl group, 3-methylbenzyloxycarbonyl group, 3,5-dimethylbenzyloxycarbonyl group, 2,4,6-trimethylbenzyloxycarbonyl group, 3-methoxybenzyloxy Carbonyl group, 3,5-dimethoxybenzyloxycarbonyl group, 2,4,6-trimethoxybenzyloxycarbonyl group, 3-difluoromethylbenzyloxycarbonyl group, 4-difluoromethylbenzyloxycarbonyl group, 4-chloro-3- Difluoromethylbenzyloxycarbonyl group, 3-chloro-4-difluoromethylbenzyloxycarbonyl group, 3-bromo-4-difluoromethylbenzyloxycarbonyl group, 3,5-difluoro-4-difluoromethylbenzyloxycarbonyl group, 2- Trifluoromethylbenzyloxycarbonyl group, 3-trifluoromethylbenzyloxycarbonyl group, 4-trifluoromethylbenzyloxycarbonyl group, 4-fluoro-3-trifluoromethylbenzyloxycarbonyl , 3-fluoro-4-trifluoromethylbenzyloxycarbonyl group, 2-pentafluoroethyl benzyloxycarbonyl group, 4-chloro-3-pentafluoroethyl benzyloxycarbonyl group, 3-chloro-4-pentafluoroethyl benzyloxy Carbonyl group, 2-pentafluoroethyl benzyloxycarbonyl group, 3-pentafluoroethyl benzyloxycarbonyl group, 4-pentafluoroethyl benzyloxycarbonyl group, 2-trifluoromethoxybenzyloxycarbonyl group, 3-trifluoromethoxybenzyloxy Carbonyl group, 4-trifluoromethoxybenzyloxycarbonyl group, 4-fluoro-3-trifluoromethoxybenzyloxycarbonyl group, 3-fluoro-4-trifluoromethoxy group Dyloxycarbonyl group, 2-pentafluoroethoxybenzyloxycarbonyl group, 3-pentafluoroethoxybenzyloxycarbonyl group, 4-pentafluoroethoxybenzyloxycarbonyl group, 3-chloro-4-trifluoromethoxybenzyloxycarbonyl group, 3 -Chloro-4-pentafluoroethoxybenzyloxycarbonyl group, 2- (2-trifluoromethylphenyl) ethoxycarbonyl group, 2- (3-trifluoromethylphenyl) ethoxycarbonyl group, 2- (4-trifluoromethylphenyl) ) Ethoxycarbonyl group, (2-trifluoromethoxyphenyl) methoxycarbonyl group, (3-trifluoromethoxyphenyl) methoxycarbonyl group, 2- (4-trifluoromethoxyphenyl) methoxy group Bonyl, 2- (2-pentafluoroethoxyphenyl) ethoxycarbonyl, 2- (3-pentafluoroethoxyphenyl) ethoxycarbonyl, 2- (4-pentafluoroethoxyphenyl) ethoxycarbonyl, 3- (2- Trifluoromethylphenyl) propoxycarbonyl group, 3- (3-trifluoromethylphenyl) propoxycarbonyl group, 3- (4-trifluoromethylphenyl) propoxycarbonyl group, 3- (2-trifluoromethylphenyl) propoxycarbonyl group 3- (3-trifluoromethoxyphenyl) propoxycarbonyl group, 3- (4-trifluoromethoxyphenyl) propoxycarbonyl group, 3- (3-pentafluoroethoxyphenyl) propoxycarbonyl group, 3- (4-pentafluoro) Ethoxyphenyl) propoxycarbonyl group, 4- (3-pentafluoroethoxyphenyl) butoxycarbonyl group, 5- (4-trifluoromethylphenyl) pentyloxycarbonyl group, 4- (4-trifluoromethylphenyl) pentyloxycarbonyl group 4- (4-trifluoromethoxyphenyl) pentyloxycarbonyl group, 6- (3-trifluoromethylphenyl) hexyloxycarbonyl group, 6- (4-trifluoromethylphenyl) hexyloxycarbonyl group, 6- (4 Phenyl-C1-6 alkoxycarbonyl group such as trifluoromethoxyphenyl) hexyloxycarbonyl group (a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1 group on the phenyl ring 1-5 from selected group the group consisting of 6 alkoxy group, preferably mention may be made of may) also be 1-3 substituents.

  A phenyl C1-6 alkoxycarbonyl group (on the phenyl ring, selected from the group consisting of a halogen atom, a cyano group, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group As at least one kind of group may be substituted), for example, benzyloxycarbonyl group, phenylethoxycarbonyl group, 3-phenylpropoxycarbonyl group, 2-phenylpropoxycarbonyl group, 4-phenylbutoxycarbonyl group, 5 -Phenyl pentoxy carbonyl group, 4-phenyl pentoxy carbonyl group, 6-phenyl hexyl oxycarbonyl group, 2-fluoro benzyl oxycarbonyl group, 3- fluoro benzyl oxycarbonyl group, 4- fluoro benzyl oxycarbonyl group, 2- ( 2 Fluorophenyl) ethoxycarbonyl group, 1- (3-fluorophenyl) ethoxycarbonyl group, 2- (4-fluorophenyl) ethoxycarbonyl group, 2-chlorobenzyloxycarbonyl group, 3-chlorobenzyloxycarbonyl group, 4-chloro Benzyloxycarbonyl group, 2- (2-bromophenyl) ethoxycarbonyl group, 1- (3-chlorophenyl) ethoxycarbonyl group, 2- (4-iodophenyl) ethoxycarbonyl group, 2- (2,3-dichlorophenyl) ethoxy Carbonyl group, (2,4,6-trichlorophenyl) methoxycarbonyl group, (2,3,4,5,6-pentafluorophenyl) methoxycarbonyl group, 2-cyanobenzyloxycarbonyl group, 3-cyanobenzyloxycarbonyl Group, 4-cyanobe Dyloxycarbonyl group, 2,4-dicyanobenzyloxycarbonyl group, 3,4,5-tricyanobenzyloxycarbonyl group, 2-cyanophenylethoxycarbonyl group, 3-cyanophenylethoxycarbonyl group, 4-cyanophenylethoxycarbonyl group Group, 2-methylbenzyloxycarbonyl group, 2,4-dimethylbenzyloxycarbonyl group, 2,4,6-trimethylbenzyloxycarbonyl group, 2-trifluoromethylbenzylXycarbonyl group, 3-trifluoromethylbenzyloxycarbonyl Group, 4-trifluoromethylbenzyloxycarbonyl group, 2-methoxybenzyloxycarbonyl group, 2,4-dimethoxybenzyloxycarbonyl group, 2,4,6-trimethoxybenzyloxycarbonyl group, 2-trif Luoromethoxybenzyl oxoxycarbonyl group, 3-trifluoromethoxybenzyloxycarbonyl group, 4-trifluoromethoxybenzyloxycarbonyl group, 2- (2-trifluoromethylphenyl) ethoxycarbonyl group, 2- (3-trifluoromethyl) Phenyl) ethoxycarbonyl group, 2- (4-trifluoromethylphenyl) ethoxycarbonyl group, 2- (2-trifluoromethoxyphenyl) ethoxycarbonyl group, 2- (3-trifluoromethoxyphenyl) ethoxycarbonyl group, 2- (4-trifluoromethoxyphenyl) ethoxycarbonyl group, 3- (2-trifluoromethylphenyl) propoxycarbonyl group, 3- (3-trifluoromethylphenyl) propoxycarbonyl group, 3- (4-trifluoromethylphenyl) ) Propoxycarbonyl group, 3- (2-trifluoromethoxyphenyl) propoxycarbonyl group, 3- (3-trifluoromethoxyphenyl) propoxycarbonyl group, 3- (4-trifluoromethoxyphenyl) propoxycarbonyl group, 3- (3- (4-trifluoromethoxyphenyl) propoxycarbonyl group, 4-biphenylyl) propoxycarbonyl group, 4- (4-biphenylyl) butoxycarbonyl group, 5- (4-biphenylyl) pentoxy carbonyl group, 4- (3-trifluoromethylphenyl) butoxycarbonyl group, 5- (4-biphenylyl) butoxycarbonyl group Trifluoromethylphenyl) pentoxy carbonyl group, 4- (4- trifluoromethyl phenyl) pentoxy carbonyl group, 4- (4- trifluoro methoxy phenyl) pentoxy carbonyl group, 6- (3- trifluoromethyl phenyl) Hexyloxycarbo Phenyl C1-6 alkoxycarbonyl groups such as nyl group, 6- (4-trifluoromethylphenyl) hexyloxycarbonyl group, 6- (4-trifluoromethoxyphenyl) hexyloxycarbonyl group (a halogen atom on a phenyl ring; 1 to 5, preferably 1 to 3 groups selected from the group consisting of a cyano group, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group May be mentioned.

  A phenyl C1-6 alkyl group (wherein at least one of a group selected from the group consisting of a halogen atom and a halogen-substituted or unsubstituted C1-6 alkyl group may be substituted on the phenyl ring), 1 to 5 groups, preferably 1 group, selected from the group consisting of unsubstituted phenyl C1-6 alkyl groups and phenyl rings constituting these groups from halogen atoms and halogen substituted or unsubstituted C1-6 alkyl groups To 3 -substituted group, for example, benzyl group, 1-phenethyl group, 2-phenethyl group, 3-phenylpropyl group, 2-phenylpropyl group, 4-phenylbutyl group, 5-phenylpentyl group , 4-phenylpentyl group, 6-phenylhexyl group, 2-fluorobenzyl group, 3-fluorobenzyl group, 4-fluorobenzyl group, 2-chloro Benzyl, 3-chlorobenzyl, 4-chlorobenzyl, 2-bromobenzyl, 3-bromobenzyl, 4-bromobenzyl, 2-iodobenzyl, 3-iodobenzyl, 4-iodobenzyl , 2,3-difluorobenzyl group, 3,4-difluorobenzyl group, 3,5-difluorobenzyl group, 2,4-difluorobenzyl group, 2,6-difluorobenzyl group, 2,3,4,5,6 -Pentafluorobenzyl group, 2,3-dichlorobenzyl group, 3,4-dichlorobenzyl group, 3,5-dichlorobenzyl group, 2,4-dichlorobenzyl group, 2,6-dichlorobenzyl group, 2-trifluoro Methyl benzyl group, 3-trifluoromethylbenzyl group, 4-trifluoromethylbenzyl group, 2-methylbenzyl group, 2,3-dimethyl Ndidyl group, 2,4,6-trimethylbenzyl group, 3,5-ditrifluoromethylbenzyl group, 2- (2-trifluoromethylphenyl) ethyl group, 2- (3-trifluoromethylphenyl) ethyl group, 2 -(4-Trifluoromethylphenyl) ethyl group, 3- (2-trifluoromethylphenyl) propyl group, 3- (3-trifluoromethylphenyl) propyl group, 3- (4-trifluoromethylphenyl) propyl group 3- (2-trifluoromethylphenyl) propyl group, 5- (4-trifluoromethylphenyl) pentyl group, 4- (4-trifluoromethylphenyl) pentyl group, 6- (3-trifluoromethylphenyl) group A hexyl group, 6- (4-trifluoromethylphenyl) hexyl group etc. can be mentioned.

  The piperidinyl C1-6 alkyl group (on the piperidine ring, at least one phenoxy group (on the phenyl ring, at least one halogen-substituted or unsubstituted C1-6 alkyl group may optionally be substituted) is substituted As piperidine-1-ylmethyl group, piperidin-2-ylethyl group, piperidin-3-ylpropyl group, piperidin-4-ylbutyl group, piperidin-1-ylpentyl group, piperidine-2 -Ylhexyl group, 4-phenoxypiperidin-1-ylmethyl group, 2- (4-phenoxypiperidin-1-yl) ethyl group, 3- (4-phenoxypiperidin-1-yl) propyl group, 4- (4-phenoxy) Piperidin-1-yl) butyl group, 5- (4-phenoxypiperidin-1-yl) pentyl group, 6- (6) -Phenoxypiperidin-1-yl) hexyl group, 4- (3-methylphenoxy) piperidin-1-ylmethyl group, 4- (2,5-dimethylphenoxy) piperidin-1-ylmethyl group, 4- (2,4,4, 6-trimethylphenoxy) piperidin-1-ylmethyl group, 4- (3,5-ditrifluoromethylphenoxy) piperidin-1-ylmethyl group, 4- (2-trifluoromethylphenoxy) piperidin-1-ylmethyl group, 2- [4- (2-trifluoromethylphenoxy) piperidin-1-yl] ethyl group, 3- [4- (2-trifluoromethylphenoxy) piperidin-1-yl] propyl group, 4- [4- (2- (2- (2-trifluoromethylphenoxy) piperidinyl) -propyl] Trifluoromethylphenoxy) piperidin-1-yl] butyl group, 5- [4- (2-trifluoromethylphenoxy) Piperidin-1-yl] pentyl group, 6- [4- (2-trifluoromethylphenoxy) piperidin-1-yl] hexyl group, 4- (3-trifluoromethylphenoxy) piperidin-1-ylmethyl group, 2- [4- (3-Trifluoromethylphenoxy) piperidin-1-yl] ethyl group, 3- [4- (3-trifluoromethylphenoxy) piperidin-1-yl] propyl group, 4- [4- (3- (3- (3-trifluoromethyl) phenyl) propyl group Trifluoromethylphenoxy) piperidin-1-yl] butyl group, 5- [4- (3-trifluoromethylphenoxy) piperidin-1-yl] pentyl group, 6- [4- (3-trifluoromethylphenoxy) piperidine -1-yl] hexyl group, 4- (4-trifluoromethylphenoxy) piperidin-1-ylmethyl group, 2- [4- (4-) Trifluoromethylphenoxy) piperidin-1-yl] ethyl group, 3- [4- (4-trifluoromethylphenoxy) piperidin-1-yl] propyl group, 4- [4- (4-trifluoromethylphenoxy) piperidine -1-yl] butyl group, 5- [4- (4-trifluoromethylphenoxy) piperidin-1-yl] pentyl group, 6- [4- (4-trifluoromethylphenoxy) piperidin-1-yl] hexyl And the like piperidinyl C.sub.1-6 alkyl group (on the piperidine ring, a phenoxy group as a substituent (on the phenyl ring, 1 to 5 halogen-substituted or unsubstituted C.sub.1-6 alkyl groups as a substituent, preferably And the like) may be included.

Phenyl group (on the phenyl ring, halogen atom; halogen substituted or unsubstituted C1-6 alkyl group; halogen substituted or unsubstituted C1-6 alkoxy group; C1-6 alkyl group as a substituent and phenyl C1-6 alkyl And at least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group is substituted on the phenyl ring. An amino group which may have a group selected from the group consisting of: phenoxy group [on a phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 At least one group selected from the group consisting of alkoxy groups may be substituted]; phenyl C1- At least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group, and a halogen-substituted or unsubstituted C1-6 alkoxy group is substituted on an alkoxy group [phenyl ring] And at least one amino group may be substituted on the piperidine ring, and a phenyl C1-6 alkyl group (a halogen atom on the phenyl ring may be substituted on the amino group). And at least one selected from the group consisting of a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group optionally substituted) and a C1-6 alkyl group At least one of the groups selected from the group may be substituted.] And at least one of the groups selected from the group consisting of Are, for example, phenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 2-bromophenyl group, 3- Bromophenyl group, 4-bromophenyl group, 2-iodophenyl group, 3-iodophenyl group, 4-iodophenyl group, 2,3-difluorophenyl group, 3,4-difluorophenyl group, 3,5-difluorophenyl group Group, 2,4-difluorophenyl group, 2,6-difluorophenyl group, 2,3-dichlorophenyl group, 3,4-dichlorophenyl group, 3,5-dichlorophenyl group, 2,4-dichlorophenyl group, 2,6- Dichlorophenyl group, 3,4,5-trifluorophenyl group, 3,4,5-trichlorophenyl group 2, 4,6-trifluorophenyl group, 2,3,4,5,6-pentafluorophenyl group, 2,4,6-trichlorophenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group Group, 2,4-dimethylphenyl group, 3,4,5-trimethylphenyl group, 3,5-ditrifluoromethylphenyl group, 2-methyl-3-chlorophenyl group, 3-methyl-4-chlorophenyl group, 2- Chloro-4-methylphenyl group, 2-methyl-3-fluorophenyl group, 2-trifluoromethylphenyl group, 3-trifluoromethylphenyl group, 4-trifluoromethylphenyl group, 2-pentafluoroethylphenyl group, 3-pentafluoroethylphenyl group, 4-pentafluoroethylphenyl group, 2-isopropylphenyl group, 3-isopropyl Pirphenyl group, 4-isopropylphenyl group, 2-tert-butylphenyl group, 3-tert-butylphenyl group, 4-tert-butylphenyl group, 2-sec-butylphenyl group, 3-sec-butylphenyl group, 4 -Sec-butylphenyl group, 2-n-heptafluoropropylphenyl group, 3-n-heptafluoropropylphenyl group, 4-n-heptafluoropropylphenyl group, 4-pentylphenyl group, 4-hexylphenyl group, 2 -Methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 2-methoxy-3-chlorophenyl group, 2-fluoro-3-methoxyphenyl group, 2-fluoro-4-methoxyphenyl group, 2,6- Dimethoxyphenyl group, 2,4,6-trimethoxyphenyl group, 3,5-di Trifluoromethoxyphenyl group, 2-trifluoromethoxyphenyl group, 3-trifluoromethoxyphenyl group, 4-trifluoromethoxyphenyl group, 2-pentafluoroethoxyphenyl group, 3-pentafluoroethoxyphenyl group, 4-pentafluoro Ethoxyphenyl group, 2-isopropoxyphenyl group, 3-isopropoxyphenyl group, 4-isopropoxyphenyl group, 2-tert-butoxyphenyl group, 3-tert-butoxyphenyl group, 4-tert-butoxyphenyl group, 2 -Sec-butoxyphenyl group, 3-sec-butoxyphenyl group, 4-sec-butoxyphenyl group, 2-n-heptafluoropropoxyphenyl group, 3-n-heptafluoropropoxyphenyl group, 4-n-heptafluoropropoxy group Fen Group, 4-pentyloxyphenyl group, 4-hexyloxyphenyl group, 3-aminophenyl group, 4-methylaminophenyl group, 4-dimethylaminophenyl group, 3-methylaminophenyl group, 3-dimethylaminophenyl group , 4-ethylaminophenyl group, 4-diethylaminophenyl group, 4-n-propylaminophenyl group, 4-di-n-propylaminophenyl group, 44-n-butylaminophenyl group, 4-di-n-butyl group Aminophenyl group, 4-n-pentylaminophenyl group, 4-di-n-pentylaminophenyl group, 4-n-hexylaminophenyl group, 4-di-n-hexylaminophenyl group, 4-benzylaminophenyl group , 4- (2-fluorobenzylamino) phenyl group, 4- (3-fluorobenzylamino) phenyl group, 4- (4- (2-fluorobenzylamino) phenyl group) -Fluorobenzylamino) phenyl group, 4- (2,3-difluorobenzylamino) phenyl group, 4- (2,4-difluorobenzylamino) phenyl group, 4- (3,4-difluorobenzylamino) phenyl group, 4- (3,5-difluorobenzylamino) phenyl group, 4- (2-chlorobenzylamino) phenyl group, 4- (3-chlorobenzylamino) phenyl group, 4- (4-chlorobenzylamino) phenyl group, 4- (2-bromobenzylamino) phenyl group, 4- (3-bromobenzylamino) phenyl group, 4- (4-bromobenzylamino) phenyl group, 4- (2,3-dichlorobenzylamino) phenyl group, 4- (2,4-dichlorobenzylamino) phenyl group, 4- (3,4-dichlorobenzylamino) phenyl group, 4- (4- (2,4-dichlorobenzylamino) phenyl group) 3,5-Dichlorobenzylamino) phenyl group, 4- (2-methylbenzylamino) phenyl group, 4- (3-methylbenzylamino) phenyl group, 4- (4-methylbenzylamino) phenyl group, 4- (4- (4-methylbenzylamino) phenyl group) 2-ethylbenzylamino) phenyl group, 4- (3-ethylbenzylamino) phenyl group, 4- (4-ethylbenzylamino) phenyl group, 4- (4-n-propylbenzylamino) phenyl group, 4- (4- 4-tert-butylbenzylamino) phenyl group, 4- (4-n-butylbenzylamino) phenyl group, 4- (2-trifluoromethylbenzylamino) phenyl group, 4- (3-trifluoromethylbenzylamino) Phenyl group, 4- (4-trifluoromethylbenzylamino) phenyl group, 4- (2-pentafluoroethyl benzyl) Mino) phenyl group, 4- (3-pentafluoroethylbenzylamino) phenyl group, 4- (2,3-dimethylbenzylamino) phenyl group, 4- (3, 4, 5- trimethylbenzylamino) phenyl group, 4 4- (4-pentylbenzylamino) phenyl group, 4- (4-hexylbenzylamino) phenyl group, 4- (3-methoxybenzylamino) phenyl group, 4- (3,5-dimethoxybenzylamino) phenyl group, 4 -(2,4,6-trimethoxybenzylamino) phenyl, 4- (2-trifluoromethoxybenzylamino) phenyl, 4- (3-trifluoromethoxybenzylamino) phenyl, 4- (4-tri- Fluoromethoxybenzylamino) phenyl group, 4- (2-pentafluoroethoxybenzylamino) phenyl group, -(3-pentafluoroethoxybenzylamino) phenyl group, 4- (4-pentafluoroethoxybenzylamino) phenyl group, phenethylamino) phenyl group, 4- (2-fluorophenethylamino) phenyl group, 4- (3- Fluorophenethylamino) phenyl group, 4- (4-fluorophenethylamino) phenyl group, 4- (2,3-difluorophenethylamino) phenyl group, 4- (2,4-difluorophenethylamino) phenyl group, 4- (4- 3,4-Difluorophenethylamino) phenyl group, 4- (3,5-difluorophenethylamino) phenyl group, 4- (2-chlorophenethylamino) phenyl group, 4- (3-chlorophenethylamino) phenyl group, 4 -(4-chlorophenethylamino) phenyl group, 4- (2-bromophen) 4- (3-bromophenethylamino) phenyl group, 4- (4-bromophenethylamino) phenyl group, 4- (2,3-dichlorophenethylamino) phenyl group, 4- (2,4-bromophenethylamino) phenyl group Dichlorophenethylamino) phenyl group, 4- (3,4-dichlorophenethylamino) phenyl group, 4- (3,5-dichlorophenethylamino) phenyl group, 4- (2-methylphenethylamino) phenyl group, 4- (4- (2-methylphenethylamino) phenyl group) 3-Methylphenethylamino) phenyl group, 4- (4-methylphenethylamino) phenyl group, 4- (4-ethylphenethylamino) phenyl group, 4- (4-propylphenethylamino) phenyl group, 4- (4-methylphenethylamino) phenyl group tert-Butylphenethylamino) phenyl group, 4- (2-trifluoromethylphenethylamino) phenyl 4- (3-trifluoromethylphenethylamino) phenyl group, 4- (4-trifluoromethylphenethylamino) phenyl group, 4- (2-pentafluoroethylphenethylamino) phenyl group, 4- (3-pentafluorophenyl) Ethylphenethylamino) phenyl group, 4- (2,3-dimethylphenethylamino) phenyl group, 4- (2-trifluoromethoxyphenethylamino) phenyl group, 4- (3-trifluoromethoxyphenethylamino) phenyl group, 4 -(4-Trifluoromethoxyphenethylamino) phenyl, 4- (2-pentafluoroethoxyphenethylamino) phenyl, 4- (3-pentafluoroethoxyphenethylamino) phenyl, 4- (4-pentafluoroethoxyphenethyl) Amino) phenyl group, 4- (3- Phenylpropylamino) phenyl group, 4- [3- (2-fluorophenyl) propylamino] phenyl group, 4- [3- (3-fluorophenyl) propylamino] phenyl group, 4- [3- (4-fluoro) Phenyl) propylamino] phenyl group, 4- [3- (2,3-difluorophenyl) propylamino] phenyl group, 4- [3- (2,4-difluorophenyl) propylamino] phenyl group, 4- [3 -(3,4-difluorophenyl) propylamino] phenyl group, 4- [3- (3,5-difluorophenyl) propylamino] phenyl group, 4- [3- (2-chlorophenyl) propylamino] phenyl group, 4- [3- (3-chlorophenyl) propylamino] phenyl group, 4- [3- (4-chlorophenyl) propylamino] fe Group, 4- [3- (2-bromophenyl) propylamino] phenyl group, 4- [3- (3-bromophenyl) propylamino] phenyl group, 4- [3- (4-bromophenyl) propylamino ] Phenyl group, 4- [3- (2,3-dichlorophenyl) propylamino] phenyl group, 4- [3- (2,4-dichlorophenyl) propylamino] phenyl group, 4- [3- (3,4- (3,4-) Dichlorophenyl) propylamino] phenyl group, 4- [3- (3,5-dichlorophenyl) propylamino] phenyl group, 4- [3- (2-methylphenyl) propylamino] phenyl group, 4- [3- (3) -Methylphenyl) propylamino] phenyl group, 4- [3- (4-methylphenyl) propylamino] phenyl group, 4- [3- (2-ethylphenyl) group Pylamino] phenyl group, 4- [3- (3-ethylphenyl) propylamino] phenyl group, 4- [3- (4-ethylphenyl) propylamino] phenyl group, 4- [3- (4-propylphenyl) phenyl group Propylamino] phenyl group, 4- [3- (4-tert-butyl]


Phenyl) propylamino] phenyl group, 4- [3- (4-butylphenyl) propylamino] phenyl group, 4- [3- (2-trifluoromethylphenyl) propylamino] phenyl group, 4- [3-triyl Fluoromethylphenyl] propylamino] phenyl group, 4- [3- (4-trifluoromethylphenyl) propylamino] phenyl group, 4- [3- (2-pentafluoroethylphenyl) propylamino] phenyl group, 4- [3- (3-Pentafluoroethylphenyl) propylamino] phenyl group, 4- [3- (2,3-dimethylphenyl) propylamino] phenyl group, 4- [3- (3,4,5-trimethylphenyl) group ) Propylamino] phenyl group, 4- [3- (4-pentylphenyl) propylamino] phenyl group, 4- [3 (4-Hexylphenyl) propylamino] phenyl group, 4- [3- (2-trifluoromethoxyphenyl) propylamino] phenyl group, 4- [3-trifluoromethoxyphenyl] propylamino] phenyl group, 4- [3 3- (4-Trifluoromethoxyphenyl) propylamino] phenyl group, 4- [3- (2-pentafluoroethoxyphenyl) propylamino] phenyl group, 4- [3- (3-pentafluoroethoxyphenyl) propylamino ] Phenyl group, 4- [3- (4-pentafluoroethoxyphenyl) propylamino] phenyl group, 2-phenoxyphenyl group, 3-phenoxyphenyl group, 4-phenoxyphenyl group, 2- (2-chlorophenoxy) phenyl Group, 2- (3-chlorophenoxy) phenyl group, 2- (4-) Rolophenoxy) phenyl group, 3- (2-chlorophenoxy) phenyl group, 3- (3-chlorophenoxy) phenyl group, 3- (4-chlorophenoxy) phenyl group, 4- (2-chlorophenoxy) phenyl group, 4- (3-chlorophenoxy) phenyl group, 4- (4-chlorophenoxy) phenyl group, 3- (4-methylphenoxy) phenyl group, 2- (3,4-dimethylphenoxy) phenyl group, 4- (2) 4,6-trimethylphenoxy) phenyl group, 2- (2-trifluoromethylphenoxy) phenyl group, 2- (3-trifluoromethylphenoxy) phenyl group, 2- (4-trifluoromethylphenoxy) phenyl group, 3- (2-trifluoromethylphenoxy) phenyl group, 3- (3-trifluoromethylphenoxy) phenyl group, 3- (4-trifluoromethylphenoxy) phenyl group, 4- (2-trifluoromethylphenoxy) phenyl group, 4- (3-trifluoromethylphenoxy) phenyl group, 4- (4-trifluoromethylphenoxy) phenyl group Group, 3- (4-methoxyphenoxy) phenyl group, 2- (3,4-dimethoxyphenoxy) phenyl group, 4- (2,4,6-trimethoxyphenoxy) phenyl group, 2- (2-trifluoromethoxy) group Phenoxy) phenyl group, 2- (3-trifluoromethoxyphenoxy) phenyl group, 2- (4-trifluoromethoxyphenoxy) phenyl group, 3- (2-trifluoromethoxyphenoxy) phenyl group, 3- (3-triyl) Fluoromethoxyphenoxy) phenyl group, 3- (4-trifluoromethoxyphenoxy) phenyl Nyl group, 4- (2-trifluoromethoxyphenoxy) phenyl group, 4- (3-trifluoromethoxyphenoxy) phenyl group, 4- (4-trifluoromethoxyphenoxy) phenyl group, 4-benzyloxyphenyl group, 4 -(2-phenylethoxy) phenyl group, 4- (3-phenylpropoxy) phenyl group, 4- (4-phenylbutoxy) phenyl group, 4- (5-phenylpentoxy) phenyl group, 4- (6-phenyl group) Hexyloxy) phenyl group, 4- (4-fluorobenzyloxy) phenyl group, 4- (3-fluorobenzyloxy) phenyl group, 4- (2-fluorobenzyloxy) phenyl group, 4- (4-chlorobenzyloxy) ) Phenyl group, 4- (3-chlorobenzyloxy) phenyl group, 4- (2-chlorobenzyl oxy) ) Phenyl group, 3- (4-methylbenzyloxy) phenyl group, 2- (2,4-dimethylbenzyloxy) phenyl group, 4- (2,4,6-trimethylbenzyloxy) phenyl group, 4- (2 -Trifluoromethylbenzyloxy) phenyl group, 4- (3-trifluoromethylbenzyloxy) phenyl group, 4- (4-trifluoromethylbenzyloxy) phenyl group, 3- (4-methoxylbenzyloxy) phenyl group, 2- (2,4-dimethoxybenzyloxy) phenyl group, 4- (2,4,6-trimethoxybenzyloxy) phenyl group, 4- (2-trifluoromethoxybenzyloxy) phenyl group, 4- (3- Trifluoromethoxybenzyloxy) phenyl group, 4- (4-trifluoromethoxybenzyloxy) phenyl group, 4 -(4-fluorophenylethoxy) phenyl group, 4- (3-fluorophenylethoxy) phenyl group, 4- (2-fluorophenylethoxy) phenyl group, 4- (4-chlorophenylethoxy) phenyl group, 4- (3 -Chlorophenylethoxy) phenyl group, 4- (2-chlorophenylethoxy) phenyl group, 4- (2-trifluoromethylphenylethoxy) phenyl group, 4- (3-trifluoromethylphenylethoxy) phenyl group, 4- (4 -Trifluoromethylphenylethoxy) phenyl group, 4- (2-trifluoromethoxyphenylethoxy) phenyl group, 4- (3-trifluoromethoxyphenylethoxy) phenyl group, 4- (4-trifluoromethoxyphenylethoxy) phenyl Group, 4- [3- (4-fluorophenyl) Propoxy] phenyl group, 4- [3- (3-fluorophenyl) propoxy] phenyl group, 4- [3- (2-fluorophenyl) propoxy] phenyl group, 4- [3- (2-trifluoromethylphenyl) group Propoxy] phenyl group, 4- [3- (3-trifluoromethylphenyl) propoxy] phenyl group, 4- [3- (4-trifluoromethylphenyl) propoxy] phenyl group, 4- [3- (2-triphenyl) propoxy group Fluoromethylphenyl) propoxy] phenyl group, 4- [3- (3-trifluoromethoxyphenyl) propoxy] phenyl group, 3- (4-trifluoromethoxyphenyl) propoxy] phenyl group, 4- [4- (3-) Trifluoromethylphenyl) butoxy] phenyl group, 4- [5- (4-trifluoromethylphenyl) pentoxy group ] Phenyl group, 4- [4- (4-trifluoromethoxyphenyl) pentoxy] phenyl group, 4- [6- (3-trifluoromethylphenyl) hexyloxy] phenyl group, 4- [6- (4- tri- Fluoromethylphenyl) hexyloxy] phenyl group, 4- [6- (4-trifluoromethoxyphenyl) hexyloxy] phenyl group, 3- (piperidin-1-yl) phenyl group, 2- (4-benzylaminopiperidine- 1-yl) phenyl group, 2- (3-benzylaminopiperidin-1-yl) phenyl group, 2- (4-benzylaminopiperidin-1-yl) phenyl group, 2- (4-benzylaminopiperidine-1-) Yl) phenyl group, 2- (4-benzylaminopiperidin-1-yl) phenyl group, 2- [4- (4-chlorobenzyl) group Minopiperidin-1-yl] phenyl group, 2- [2- (2,4-dichlorobenzyl) aminopiperidin-1-yl] phenyl group, 2- [4- (2,4,6-trichlorobenzyl) aminopiperidine -1-yl] phenyl group, 2- [4- (4-methylbenzyl) aminopiperidin-1-yl] phenyl group, 2- [4- (2,4-dimethylbenzyl) aminopiperidin-1-yl] phenyl Group, 2- [4- (2,4,6-trimethylbenzyl) aminopiperidin-1-yl] phenyl group, 2- [4- (4-trifluoromethylbenzyl) aminopiperidin-1-yl] phenyl group, 2- [4- (2,4-ditrifluoromethylbenzyl) piperidin-1-yl] phenyl group, 2- [4- [2,4,6-tri (trifluoromethyl) benzyl] aminopipe Lysine-1-yl] phenyl group, 2- [4- (4-methoxybenzyl) aminopiperidin-1-yl] phenyl group, 2- [4- (2,4-dimethoxybenzyl) aminopiperidin-1-yl] Phenyl group, 2- [4- (2,4,6-trimethoxybenzyl) aminopiperidin-1-yl] phenyl group, 2- [4- (4-trifluoromethoxybenzyl) aminopiperidin-1-yl] phenyl Group, 2- [4- (3,5-trifluoromethoxybenzyl) aminopiperidin-1-yl] phenyl group, 2- [4- [2,4,6-tri (trifluoromethoxy) benzyl] aminopiperidine- 1-yl] phenyl group, 4- (4-methylaminopiperidin-1-yl) phenyl group, 4- (4-dimethylaminopiperidin-1-yl) phenyl group, 4- (4-ethylamino) phenyl group 4- (4-diethylaminopiperidin-1-yl) phenyl group, 4- (4-n-propylaminopiperidin-1-yl) phenyl group, 4- (4- (4- (4-diethylaminopiperidin-1-yl) phenyl) group; Di n-propylamino) piperidin-1-yl group, 4- (4-n-butylaminopiperidin-1-yl) phenyl group, 4- [4- (N-ethyl-N-methylamino) piperidine-1 [Yl] phenyl group, 4- [4- (N-benzyl-N-methylamino) piperidin-1-yl] phenyl group, 4- (4-n-pentylaminopiperidin-1-yl) phenyl group, 4- (4- (4-n-pentylaminopiperidin-1-yl) phenyl group Phenyl group such as 4-n-hexylaminopiperidin-1-yl) phenyl group (a halogen atom on the phenyl ring; halogen substituted or unsubstituted C1-6 alkyl group; halogen substituted Or unsubstituted C.sub.1-6 alkoxy group; C.sub.1-6 alkyl group and phenyl C.sub.1-6 alkyl group as substituents [on the phenyl ring, halogen atoms, halogen substituted or unsubstituted C.sub.1-6 alkyl groups and halogen substituted or 1 to 5, preferably 1 to 3 groups selected from the group consisting of unsubstituted C1-6 alkoxy groups may have one or two groups selected from the group consisting of A group selected from the group consisting of a halogen group, a halogen-substituted or unsubstituted C1-6 alkyl group, and a halogen-substituted or unsubstituted C1-6 alkoxy group on a phenyl ring; Phenyl, preferably 1 to 3 substituents; phenyl C1-6 alkoxy group [on the phenyl ring, a halogen atom, halogen substituted or unsubstituted 1 to 5, preferably 1 to 3 groups selected from the group consisting of a C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group may be substituted] and a piperidyl group [piperidine ring Above, at least one amino group may be substituted. On the amino group, a phenyl C1-6 alkyl group (on the phenyl ring, selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group Group selected from the group consisting of 1 to 5, preferably 1 to 3 substituted groups and C.sub.1-6 alkyl group may be substituted); 1 to 5 groups, and preferably 1 to 3 groups selected from those groups) may be mentioned.

  As the biphenylyl C1-6 alkoxy group, for example, 1,1′-biphenyl-4-ylmethoxy group, 2- (1,1′-biphenyl-4-yl) ethoxy group, 3- (1,1′-biphenyl- 4-yl) propoxy group, 4- (1,1'-biphenyl-4-yl) butoxy group, 5- (1,1'-biphenyl-4-yl) pentyloxy group, 6- (1,1'-) Examples include biphenyl-4-yl) hexyloxy group and the like.

  Examples of the phenyl C3-6 alkenyloxy group which may be substituted by at least one halogen atom on the phenyl ring include, for example, 3-phenyl-2-propenyloxy group (conventional name: cinnamyloxy group), 4- Phenyl-2-butenyloxy group, 4-phenyl-3-butenyloxy group, 3- (2-fluorophenyl) -2-propenyloxy group, 3- (3-fluorophenyl) -2-propenyloxy group, 3- (4 -Fluorophenyl) -2-propenyloxy group, 3- (2,3-difluorophenyl) -2-propenyloxy group, 3- (2,4-difluorophenyl) -2-propenyloxy group, 3- (3, 3, 4-difluorophenyl) -2-propenyloxy group, 3- (3,5-difluorophenyl) -2-propenyloxy group, 3- (2- Rolophenyl) -2-propenyloxy group, 3- (3-chlorophenyl) -2-propenyloxy group, 3- (4-chlorophenyl) -2-propenyloxy group, 3- (2,4,6-trichlorophenyl)- 2-propenyloxy group, 3- (2,3,4,5,6-pentafluorophenyl) -2-propenyloxy group, 3- (2,3-dichlorophenyl) -2-propenyloxy group, 3- (2 , 4-Dichlorophenyl) -2-propenyloxy group, 3- (3,4-dichlorophenyl) -2-propenyloxy group, 3- (3,5-dichlorophenyl) -2-propenyloxy group, 3- (2-bromo) Phenyl) -2-propenyloxy group, 3- (3-bromophenyl) -2-propenyloxy group, 3- (4-bromophenyl) -2-propenyl group 4- (4-chlorophenyl) -3-butenyloxy group, 4- (2,3-dichlorophenyl) -3-butenyloxy group, 4- (2,4-dichlorophenyl) -3-butenyloxy group, 4- (3 -4) , 4-Dichlorophenyl) -3-butenyloxy, 4- (3,5-dichlorophenyl) -3-butenyloxy, 5- (4-chlorophenyl) -4-pentenyloxy, 5- (2,3-dichlorophenyl)- 4-pentenyloxy group, 5- (2,4-dichlorophenyl) -4-pentenyloxy group, 5- (3,4-dichlorophenyl) -4-pentenyloxy group, 5- (3,5-dichlorophenyl) -4- 4 Pentanyloxy group, 6- (4-chlorophenyl) -5-hexenyloxy group, 6- (2,3-dichlorophenyl) -5-hexenyl group Xy group, 6- (2,4-dichlorophenyl) -5-hexenyloxy group, 6- (3,4-dichlorophenyl) -5-hexenyloxy group, 6- (3,5-dichlorophenyl) -5-hexenyloxy group Mention may be made of a phenyl C3-6 alkenyloxy group which may be substituted by 1 to 5 and preferably 1 to 3 halogen atoms on the phenyl ring of the like.

  A phenoxy group (on the phenyl ring, at least one group selected from the group consisting of a halogen atom, a cyano group, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group May be substituted), for example, phenoxy group, 2-fluorophenoxy group, 3-fluorophenoxy group, 4-fluorophenoxy group, 2-chlorophenoxy group, 3-chlorophenoxy group, 4-chloro Phenoxy group, 2-bromophenoxy group, 3-bromophenoxy group, 4-bromo-phenoxy group, 2,3-dichlorophenoxy group, 3,4-dichlorophenoxy group, 2,4-dichlorophenoxy group, 3,4, 5-trichlorophenoxy group, 2,4,6-trichlorophenoxy group, 2,3,4,5,6-pentaful Rophenoxy group, 2-cyanophenoxy group, 3-cyanophenoxy group, 4-cyanolophenoxy group, 2-methylphenoxy group, 2,4,6-tricyanolophenoxy group, 2,3-dicyanophenoxy group, 3- Methyl phenoxy group, 4-methyl phenoxy group, 2-ethyl phenoxy group, 3-ethyl phenoxy group, 4-ethyl phenoxy group, 4-n-propyl phenoxy group, 4-tert-butyl phenoxy group, 4-n-butyl Phenoxy group, 2-trifluoromethylphenoxy group, 3-trifluoromethylphenoxy group, 4-trifluoromethylphenoxy group, 2-pentafluoroethylphenoxy group, 3-pentafluoroethylphenoxy group, 2,3-dimethylphenoxy group 3,4,5-trimethylphenoxy group, 4-n-pentyl group Noxy group, 4-n-hexylphenoxy group, 2-methoxyphenoxy group, 3-methoxyphenoxy group, 4-methoxyphenoxy group, 2-ethoxyphenoxy group, 3-ethoxyphenoxy group, 4-ethoxyphenoxy group, 4-n -Propoxy phenoxy group, 4-tert- butoxy phenoxy group, 4- n-butoxy phenoxy group, 2- trifluoro methoxy phenoxy group, 3- trifluoro methoxy phenoxy group, 4- trifluoro methoxy phenoxy group, 2- penta fluoro ethoxy Phenoxy groups such as phenoxy group, 3-pentafluoroethoxyphenoxy group, 2,3-dimethoxyphenoxy group, 3,4,5-trimethoxyphenoxy group, 4-n-pentyloxyphenoxy group, 4-n-hexyloxyphenoxy group and the like Group (on the phenyl ring, 1 to 5, preferably 1 to 3 groups selected from the group consisting of a halogen atom, a cyano group, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group May be mentioned).

  Examples of the phenyl C1-6 alkoxycarbonyl group (wherein at least one halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted on the phenyl ring) include, for example, a benzyloxycarbonyl group, a phenylethoxycarbonyl group , 3-phenylpropoxycarbonyl group, 2-phenylpropoxycarbonyl group, 4-phenylbutoxycarbonyl group, 5-phenylpentoxycarbonyl group, 4-phenylpentoxycarbonyl group, 6-phenylhexyloxycarbonyl group, 2-methoxybenzyl group Oxycarbonyl group, 2,4-dimethoxybenzyloxycarbonyl group, 2,4,6-trimethoxybenzyloxycarbonyl group, 2-trifluoromethoxybenzyloxy carbonyl group, 3-trifluoromethoxybenzyloxycar Group, 4-trifluoromethoxybenzyloxycarbonyl group, 2- (2-trifluoromethoxyphenyl) ethoxycarbonyl group, 2- (3-trifluoromethoxyphenyl) ethoxycarbonyl group, 2- (4-trifluoromethoxyphenyl) group ) Ethoxycarbonyl group, 3- (3-trifluoromethoxyphenyl) propoxycarbonyl group, 3- (4-trifluoromethoxyphenyl) propoxycarbonyl group, 4- (4-trifluoromethoxyphenyl) pentoxy carbonyl group, 6- Phenyl C1-6 alkoxycarbonyl groups such as (4-trifluoromethoxyphenyl) hexyloxycarbonyl group (1 to 3 halogen-substituted or unsubstituted C1-6 alkoxy groups may be substituted on the phenyl ring Can be mentioned

  Examples of the phenyl C1-6 alkylcarbamoyl group which may be substituted by at least one halogen atom on the phenyl ring include, for example, benzylcarbamoyl group, 2-phenethylcarbamoyl group, 3-phenylpropylcarbamoyl group, 2-phenylpropylcarbamoyl group , 4-phenylbutylcarbamoyl group, 5-phenylpentylcarbamoyl group, 4-phenylpentylcarbamoyl group, 6-phenylhexylcarbamoyl group, 2-fluorobenzylcarbamoyl group, 3-fluorobenzylcarbamoyl group, 2,4,6-trichloro Benzylcarbamoyl group, 2,3,4,5,6-pentafluorobenzylcarbamoyl group, 4-fluorobenzylcarbamoyl group, 2-chlorobenzylcarbamoyl group, 3-chlorobenzylcarbamoyl group, -Chlorobenzylcarbamoyl group, 2-bromobenzylcarbamoyl group, 3-bromobenzylcarbamoyl group, 4-bromobenzylcarbamoyl group, 2-iodobenzylcarbamoyl group, 3-iodobenzylcarbamoyl group, 4-iodobenzylcarbamoyl group, 2, 3-difluorobenzylcarbamoyl group, 3,4-difluorobenzylcarbamoyl group, 3,5-difluorobenzylcarbamoyl group, 2,4-difluorobenzylcarbamoyl group, 2,6-difluorobenzylcarbamoyl group, 2,3-dichlorobenzylcarbamoyl group Group, 3,4-dichlorobenzylcarbamoyl group, 3,5-dichlorobenzylcarbamoyl group, 2,4-dichlorobenzylcarbamoyl group, 2,6-dichlorobenzylcarbamoyl group, etc. Gen atoms can be exemplified 1-5 which may be substituted phenyl C1~6 alkylcarbamoyl.

  Examples of the phenylthio group (on the phenyl ring, at least one halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted) include, for example, a phenylthio group, a 2-methoxyphenylthio group, and 3-methoxyphenyl. Thio group, 4-methoxyphenylthio group, 2,4-dimethoxyphenylthio group, 2,4,6-trimethoxyphenylthio group, 3,5-ditrifluoromethoxyphenylthio group, 2-trifluoromethoxyphenylthio group , 3-trifluoromethoxyphenylthio group, 4-trifluoromethoxyphenylthio group, 4-ethoxyphenylthio group, 4-pentafluoroethoxyphenylthio group, 4-propoxyphenylthio group, 4-butoxyphenylthio group, 4 -Pentyloxyphenylthio group, 4-hexyloxyphenylthio (On the phenyl ring, Cl to 6 alkoxy groups halogen-substituted or unsubstituted may also be one to three substituents) phenylthio group such as and the like.

  Examples of the phenylsulfoxide group (on the phenyl ring, at least one halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted) include, for example, phenylsulfoxide group, 2-methoxyphenylsulfoxide group, 3- Methoxyphenyl sulfoxide, 4-methoxyphenyl sulfoxide, 2,4-dimethoxyphenyl sulfoxide, 2,4,6-trimethoxyphenyl sulfoxide, 3,5-ditrifluoromethoxyphenyl sulfoxide, 2-trifluoromethoxyphenyl Phenyl sulfoxide groups such as sulfoxide group, 3-trifluoromethoxyphenyl sulfoxide group, 4-trifluoromethoxyphenyl sulfoxide group, etc. (1 to 3 halogen-substituted or unsubstituted C1-6 alkoxy groups on the phenyl ring) Mention may be made of the conversion may be).

  As the pyridyl C1-6 alkoxy group, for example, 2-pyridylmethoxy group, 3-pyridylmethoxy group, 4-pyridylmethoxy group, 2- (2-pyridyl) ethoxy group, 2- (3-pyridyl) ethoxy group, 2 -(4-pyridyl) ethoxy group, 3- (2-pyridyl) propoxy group, 3- (3-pyridyl) propoxy group, 3- (4-pyridyl) propoxy group, 4- (2-pyridyl) butoxy group, 4 -(3-Pyridyl) butoxy, 4- (4-Pyridyl) butoxy, 5- (2-Pyridyl) pentyloxy, 5- (3-Pyridyl) Pentyloxy, 5- (4-Pyridyl) Pentyloxy And 6- (2-pyridyl) hexyloxy group, 6- (3-pyridyl) hexyloxy group, 6- (4-pyridyl) hexyloxy group and the like.

  Examples of the phenyl C2-6 alkanoyl group which may be substituted by at least one halogen atom on the phenyl ring include, for example, phenyl acetyl group, 3-phenyl propionyl group, 4-phenyl butyryl group, 5-phenyl pentanoyl Group, 6-phenylhexanoyl group, 2-fluorophenylacetyl group, 3-fluorophenylacetyl group, 4-fluorophenylacetyl group, 2-chlorophenylacetyl group, 3-chlorophenylacetyl group, 4-chlorophenylacetyl group, 2- Bromophenyl acetyl group, 3-bromophenyl acetyl group, 4-bromophenyl acetyl group, 2,3-dichlorophenyl acetyl group, 2,4,6-trichlorophenyl acetyl group, 2,3,4,5,6-pentafluoro Phenylacetyl group, 3- (2-fluoro) -(3-fluorophenyl) propionyl group, 3- (4-fluorophenyl) propionyl group, 3- (2-chlorophenyl) propionyl group, 3- (3-chlorophenyl) propionyl group, 3- (3) 4-chlorophenyl) propionyl group, 3- (2-bromophenyl) propionyl group, 3- (3-bromophenyl) propionyl group, 3- (4-bromophenyl) propionyl group, 4- (4-fluorophenyl) butyryl group , 4- (3-Chlorophenyl) butyryl, 4- (4-chlorophenyl) butyryl, 5- (4-fluorophenyl) pentanoyl, 5- (3-chlorophenyl) pentanoyl, 5- (4-chlorophenyl) pentanoyl Group, 6- (4-fluorophenyl) hexanoyl group, 5- (3-chloro) group Phenyl) hexanoyl group, 6- (4-chlorophenyl) halogen atoms on the phenyl ring such as hexanoyl group can be exemplified 1-5 substituted phenyl optionally C2~6 alkanoyl group.

  Examples of the phenylcarbamoyl group (on the phenyl ring, at least one halogen-substituted or unsubstituted C1-6 alkyl group may be substituted) include, for example, phenylcarbamoyl group, 2-methylphenylcarbamoyl group, 3- Methylphenylcarbamoyl group, 4-methylphenylcarbamoyl group, 3,4-dimethylphenylcarbamoyl group, 2,4,6-trimethylphenylcarbamoyl group, 4-n-propylphenylcarbamoyl group, 4-n-butylphenylcarbamoyl group, 3-n-pentylphenylcarbamoyl group, 2-n-hexylphenylcarbamoyl group, 2-trifluoromethylphenylcarbamoyl group, 3-trifluoromethylphenylcarbamoyl group, 4-trifluoromethylphenylcarbamoyl group, N-methyl-N - Group, N- (2-methylphenyl) -N-methylcarbamoyl group, N- (3-ethylphenyl) -N-methylcarbamoyl group, N- (4-n-hexylphenyl) -N-methylcarbamoyl group N- (2-isopropylphenyl) -N-methylcarbamoyl group, N- (3-n-butylphenyl) -N-methylcarbamoyl group, N- (4-tert-butylphenyl) -N-methylcarbamoyl group, N- (4-n-pentylphenyl) -N-methylcarbamoyl group, N-benzyl-N-phenylcarbamoyl group, N-benzyl-N- (2-trifluoromethylphenyl) carbamoyl group, N-benzyl-N- (2,3-Dimethylphenyl) carbamoyl group, N-benzyl-N- (2,4,6-trimethylphenyl) carbamoyl group Group, N-benzyl-N- (3,5-ditrifluoromethylphenyl) carbamoyl group, N-benzyl-N- (3-methylphenyl) carbamoyl group, N-benzyl-N- (4-tert-butylphenyl) ) Carbamoyl group, N-benzyl-N- (2-isopropylphenyl) carbamoyl group, N-benzyl-N- (3-n-propylphenyl) carbamoyl group, N-benzyl-N- (4-ethylphenyl) carbamoyl group And the like. (A phenyl substituted or unsubstituted C1 to C6 alkyl group may be substituted on the phenyl ring. The amino group portion of the carbamoyl group is a C1 to 6 alkyl group. Or phenyl C1-6 alkyl group may be substituted).

  At least one piperidinyloxycarbonyl group (on the piperidine ring, a phenyl group as a substituent [on the phenyl ring, at least one halogen-substituted or unsubstituted C1 to C6 alkyl group may be substituted]) And the like.) Which may be substituted), for example, piperidin-1-yloxycarbonyl group, piperidin-2-yloxycarbonyl group, piperidin-3-yloxycarbonyl group, piperidin-4-yloxycarbonyl group, 1 -Phenylpiperidin-4-yloxycarbonyl group, 1,2-diphenylpiperidin-4-yloxycarbonyl group, 1,3,4-triphenylpiperidin-4-yloxycarbonyl group, 1- (2-methylphenyl) Piperidine-4-yloxycarbonyl group, 1- (3-methylphenyl) piperidine 4-yloxycarbonyl group, 1- (4-methylphenyl) piperidin-4-yloxycarbonyl group, 1- (2,4-dimethylphenyl) piperidin-4-yloxycarbonyl group, 1- (2,4,-(2,4-dimethylphenyl) piperidine) 6-trimethylphenyl) piperidin-4-yloxycarbonyl group, 1- (2-trifluoromethylphenyl) piperidin-4-yloxycarbonyl group, 1- (3-trifluoromethylphenyl) piperidin-4-yloxycarbonyl Group, 1- (3,5-ditrifluoromethylphenyl) piperidin-4-yloxycarbonyl group, 1- (4-trifluoromethylphenyl) piperidin-4-yloxycarbonyl group, 1- (2-pentafluoroethyl) group Phenyl) piperidin-4-yloxycarbonyl group, 1- (3-pentafluo) Ethylphenyl) piperidin-4-yloxycarbonyl group, 1- (4-pentafluoroethylphenyl) piperidin-4-yloxycarbonyl group, 1- (2-n-propylphenyl) piperidin-4-yloxycarbonyl group, A piperidinyloxycarbonyl group such as 1- (3-n-propylphenyl) piperidin-4-yloxycarbonyl group, 1- (4-n-propylphenyl) piperidin-4-yloxycarbonyl group, etc. (on the piperidine ring Is substituted by 1 to 3 phenyl groups [which may be substituted by 1 to 3 halogen-substituted or unsubstituted C1-6 alkyl groups on the phenyl ring] as a substituent. It can be mentioned.

A 5- to 6-membered saturated heterocyclic ring formed by R ²⁴ and R ²⁵ via an adjacent nitrogen, together with the adjacent nitrogen atom, is bonded to each other via or without a nitrogen atom, an oxygen atom or a sulfur atom And a pyrrolidinyl group, a piperazyl group, a piperidyl group, a morpholino group, a thiomorpholino group and the like.

  As a C3-8 cycloalkyl C1-6 alkyl group, for example, cyclopropylmethyl group, 2-cyclopropylethyl group, 3-cyclopropylpropyl group, 4-cyclopropylbutyl group, 4-cyclopropylpentyl group, 6 -Cyclopropylhexyl group, cyclobutylmethyl group, 2-cyclobutylethyl group, 3-cyclobutylpropyl group, 4-cyclobutylbutyl group, 4-cyclobutylpentyl group, 6-cyclobutylhexyl group, cyclopentylmethyl group, 2-cyclopentylethyl group, 3-cyclopentylpropyl group, 4-cyclopentylbutyl group, 4-cyclopentylpentyl group, 6-cyclopentylhexyl group, cyclohexylmethyl group, 2-cyclohexylethyl group, 3-cyclohexylpropyl group, 4-cyclohexylbutyl group Group 4-cyclohexylpentyl group, 6-cyclohexylhexyl group, cycloheptylmethyl group, 2-cycloheptylethyl group, 3-cycloheptylpropyl group, 4-cycloheptylbutyl group, 4-cycloheptylpentyl group, 6-cycloheptylhexyl Groups, cyclooctylmethyl group, 2-cyclooctylethyl group, 3-cyclooctylpropyl group, 4-cyclooctylbutyl group, 4-cyclooctylpentyl group, 6-cyclooctylhexyl group and the like.

  Phenyl C1-6 alkyl group (a halogen atom on the phenyl ring; cyano group; halogen substituted or unsubstituted C1-6 alkyl group; C3-8 cycloalkyl group; halogen substituted or unsubstituted C1-6 alkoxy group; An amino group which may have a C1-6 alkyl group as a substituent; C1-6 alkoxycarbonyl group; phenoxy group; phenyl C1-6 alkyl group; phenyl C2-6 alkenyl group; pyridyl group; consisting of imidazolyl group and piperidyl group As the group selected from the group, 1 to 3 groups may be substituted), for example, benzyl group, 1-phenethyl group, 2-phenethyl group, 3-phenylpropyl group, 2-phenylpropyl group, 4- Phenylbutyl group, 5-phenylpentyl group, 4-phenylpentyl group, 6-phenylhexyl group, 4-chain Nobenzyl group, 2,3-dicyanobenzyl group, 2,4,6-tricyanobenzyl group, 2- (4-cyanophenyl) ethyl group, 3- (4-cyanophenyl) propyl group, 2- (4-cyano) Phenyl) propyl group, 4- (4-cyanophenyl) butyl group, 5- (4-cyanophenyl) pentyl group, 4- (4-cyanophenyl) pentyl group, 6- (4-cyanophenyl) hexyl group, 2 -Cyanobenzyl, 2- (3-cyanophenyl) ethyl, 3- (2-cyanophenyl) propyl, 2- (2-cyanophenyl) propyl, 4- (3-cyanophenyl) butyl, 5 -(2-cyanophenyl) pentyl group, 4- (3-cyanophenyl) pentyl group, 6- (3-cyanophenyl) hexyl group, 2-fluorobenzyl group, 3-fluorobenzyl group Group, 4-fluorobenzyl group, 2-chlorobenzyl group, 3-chlorobenzyl group, 4-chlorobenzyl group, 2-bromobenzyl group, 3-bromobenzyl group, 4-bromobenzyl group, 2-iodobenzyl group, 3-iodobenzyl group, 4-iodobenzyl group, 2,3-difluorobenzyl group, 3,4-difluorobenzyl group, 3,5-difluorobenzyl group, 2,4-difluorobenzyl group, 2,6-difluorobenzyl group Group, 2,3-dichlorobenzyl group, 3,4-dichlorobenzyl group, 3,5-dichlorobenzyl group, 2,4,6-trichlorobenzyl group, 2,4-dichlorobenzyl group, 2,6-dichlorobenzyl group Group, 2-trifluoromethylbenzyl group, 2-methylbenzyl group, 2,4-dimethylbenzyl group, 2,4,6-trimethylbenzyl group , 3,5-ditrifluoromethylbenzyl group, 3-trifluoromethylbenzyl group, 4-trifluoromethylbenzyl group, 2-pentafluoroethyl benzyl group, 3-pentafluoroethyl benzyl group, 4-pentafluoroethyl benzyl group , 2-trifluoromethoxybenzyl group, 3-trifluoromethoxybenzyl group, 4-trifluoromethoxybenzyl group, 2-pentafluoroethoxybenzyl group, 3-pentafluoroethoxybenzyl group, 4-pentafluoroethoxybenzyl group, 2 -(2-trifluoromethylphenyl) ethyl group, 2- (3-trifluoromethylphenyl) ethyl group, 2- (4-trifluoromethylphenyl) ethyl group, 2-methoxybenzyl group, 2,4-dimethoxybenzyl Group, 2,4,6-trimethoxyben Group, 3,5-ditrifluoromethoxybenzyl group, 2-chloro-4-trifluoromethylbenzyl group, 3-fluoro-4-trichloromethoxybenzyl group, 2- (2-trifluoromethoxyphenyl) ethyl group, 2 -(3-Trifluoromethoxyphenyl) ethyl group, 2- (4-trifluoromethoxyphenyl) ethyl group, 2- (2-pentafluoroethoxyphenyl) ethyl group, 2- (3-pentafluoroethoxyphenyl) ethyl group , 2- (4-pentafluoroethoxyphenyl) ethyl group, 3- (2-trifluoromethylphenyl) propyl group, 3- (3-trifluoromethylphenyl) propyl group, 3- (4-trifluoromethylphenyl) group Propyl group, 3- (2-trifluoromethoxyphenyl) propyl group, 3- (3-trile Fluoromethoxyphenyl) propyl group, 3- (4-trifluoromethoxyphenyl) propyl group, 3- (3-pentafluoroethoxyphenyl) propyl group, 3- (4-pentafluoroethoxyphenyl) propyl group, 4- (4- (4-pentafluoroethoxyphenyl) propyl group) 3-pentafluoroethoxyphenyl) butyl group, 5- (4-trifluoromethylphenyl) pentyl group, 4- (4-trifluoromethylphenyl) pentyl group, 4- (4-trifluoromethoxyphenyl) pentyl group, 6 -(3-trifluoromethylphenyl) hexyl group, 6- (4-trifluoromethylphenyl) hexyl group, 6- (4-trifluoromethoxyphenyl) hexyl group, 2-cyclohexylbenzyl group, 3-cyclohexylbenzyl group, 4-cyclohexylbenzyl group, 2- (2-cyclohexyl) Phenyl) ethyl group, 2- (3-cyclohexylphenyl) ethyl group, 2- (4-cyclohexylphenyl) ethyl group, 3- (2-cyclohexylphenyl) propyl group, 3- (3-cyclohexylphenyl) propyl group, 3 -(4-cyclohexylphenyl) propyl group, 3-aminobenzyl group, 2,4-diaminobenzyl group, 2,4,6-triaminobenzyl group, 2-dimethylaminobenzyl group, 3-dimethylaminobenzyl group, 4 -Dimethylaminobenzyl group, 2- (2-dimethylaminophenyl) ethyl group, 2- (3-dimethylaminophenyl) ethyl group, 2- (4-dimethylaminophenyl) ethyl group, 3- (2-dimethylaminophenyl) group ) Propyl group, 3- (3-dimethylaminophenyl) propyl group, 3- (4-dimethylamine) Phenyl) propyl group, 2-methoxy carbonyl benzyl group, 3- methoxy carbonyl benzyl group, 4- methoxy carbonyl benzyl group, 2- (2- methoxy carbonyl phenyl) ethyl group, 2- (3- methoxy carbonyl phenyl) ethyl group, 2- (4-Methoxycarbonylphenyl) ethyl group, 3- (2-methoxycarbonylphenyl) propyl group, 3- (3-methoxycarbonylphenyl) propyl group, 3- (4-methoxycarbonylphenyl) propyl group, 2- Ethoxycarbonylbenzyl group, 3-ethoxycarbonylbenzyl group, 4-ethoxycarbonylbenzyl group, 2- (2-ethoxycarbonylphenyl) ethyl group, 2- (3-ethoxycarbonylphenyl) ethyl group, 2- (4-ethoxycarbonyl) Phenyl) ethyl group, -(2-Ethoxycarbonylphenyl) propyl, 3- (3-ethoxycarbonylphenyl) propyl, 3- (4-ethoxycarbonylphenyl) propyl, 2-phenoxybenzyl, 3-phenoxybenzyl, 4-phenoxy Benzyl group, 2-styryl benzyl group, 3-styryl benzyl group, 4-styryl benzyl group, 2- (2-phenoxyphenyl) ethyl group, 2- (3-phenoxyphenyl) ethyl group, 2- (4-phenoxyphenyl) group 4) Ethyl group, 3- (2-phenoxyphenyl) propyl group, 3- (3-phenoxyphenyl) propyl group, 3- (4-phenoxyphenyl) propyl group, 2-benzylbenzyl group, 3-benzylbenzyl group, 4 -Benzylbenzyl group, 2- (2-benzylphenyl) ethyl group, 2- (3-be) 2- (4-benzylphenyl) ethyl group, 3- (2-benzylphenyl) propyl group, 3- (3-benzylphenyl) propyl group, 3- (4-benzylphenyl) propyl group, 2 -(2-phenethyl) benzyl group, 3- (2- phenethyl) benzyl group, 4- (2- phenethyl) benzyl group, 2- (2- (1- phenethyl) phenyl) ethyl group, 2- (3- (3- (2- phenethyl) phenyl group) 2-phenethyl) phenyl) ethyl group, 2- (4- (2-phenethyl) phenyl) ethyl group, 2- (3- (2-phenethyl) phenyl) propyl group, 3- (2- (2-phenethyl) phenyl group ) Propyl group, 3- (4- (1-phenethyl) phenyl) propyl group, 2- (3-pyridyl) benzyl group, 3- (3-pyridyl) benzyl group, 4- (3-pyridyl) bee Dyl group, 2- (1-imidazolyl) benzyl group, 3- (1-imidazolyl) benzyl group, 4- (1-imidazolyl) benzyl group, 2- (1-piperidino) benzyl group, 3- (1-piperidino) A benzyl group, 4- (1-piperidino) benzyl group etc. can be mentioned.

  Biphenylyl C1-6 alkyl group (having a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group, a halogen-substituted or unsubstituted C1-6 alkoxy group and a C1-6 alkyl group as a substituent group on the phenyl ring As at least one group selected from the group consisting of amino groups which may be substituted), for example, 2-biphenylylmethyl group, 3-biphenylylmethyl group, 4-biphenylylmethyl group , 2- (2-biphenylyl) ethyl group, 2- (3-biphenylyl) ethyl group, 2- (4-biphenylyl) ethyl group, 3- (2-biphenylyl) propyl group, 3- (3-biphenylyl) propyl group , 3- (4-biphenylyl) propyl group, 4- (4-biphenylyl) butyl group, 5- (4-biphenylyl) pentyl group, 6- (4 Biphenylyl) hexyl group, 2′-fluoro-2-biphenylylmethyl group, 2′-fluoro-3-biphenylylmethyl group, 2′-fluoro-4-biphenylylmethyl group, 3′-fluoro-2-biphenylyl Methyl group, 3'-fluoro-3-biphenylylmethyl group, 3'-fluoro-4-biphenylylmethyl group, 4'-fluoro-2-biphenylylmethyl group, 4'-fluoro-3-biphenylylmethyl group 4′-fluoro-4-biphenylylmethyl group, 2′-chloro-2-biphenylylmethyl group, 2′-chloro-3-biphenylylmethyl group, 2′-chloro-4-biphenylylmethyl group, 3 '-Chloro-2-biphenylylmethyl group, 3'-chloro-3-biphenylylmethyl group, 3'-chloro-4-biphenylylmethyl group, 4'-chloro-2-bi Phenyrylmethyl group, 4'-chloro-3-biphenylylmethyl group, 4'-chloro-4-biphenylylmethyl group, 2 ', 4'-dichloro-4-biphenylylmethyl group, 2', 4 ', 6' -Trichloro-3-biphenylylmethyl group, 3 ', 5'-ditrifluoromethyl-4-biphenylylmethyl group, 2', 3 ', 4', 5 ', 6'-pentafluoro-3-biphenylylmethyl Group, 2'-methyl-2-biphenylylmethyl group, 2'-methyl-3-biphenylylmethyl group, 2'-methyl-4-biphenylylmethyl group, 3'-methyl-2-biphenylylmethyl group, 3'-methyl-3-biphenylylmethyl group, 3'-methyl-4-biphenylylmethyl group, 4'-methyl-2-biphenylylmethyl group, 4'-methyl-3-biphenylylmethyl group, 4 ' -Methyl -4-biphenylylmethyl group, 2'-trifluoromethyl-2-biphenylylmethyl group, 2'-trifluoromethyl-3-biphenylylmethyl group, 2'-trifluoromethyl-4-biphenylylmethyl group, 3'-trifluoromethyl-2-biphenylylmethyl group, 3'-trifluoromethyl-3-biphenylylmethyl group, 3'-trifluoromethyl-4-biphenylylmethyl group, 4'-trifluoromethyl-2 -Biphenylyl methyl group, 4'- trifluoromethyl 3- biphenylyl methyl group, 4'- trifluoromethyl 4- biphenylyl methyl group, 2'- methoxy 2- biphenylyl methyl group, 2'- methoxy -3-biphenylylmethyl group, 2'-methoxy-4-biphenylylmethyl group, 3'-methoxy-2-biphenylylmethyl group, 3 -Methoxy-3-biphenylylmethyl group, 2 ', 4'-dimethoxy-3-biphenylylmethyl group, 2', 4 ', 6'-trimethoxy-4-biphenylylmethyl group, 2'-methoxy-4' group -Trifluoromethyl-2-biphenylylmethyl group, 3'-methyl-4'-trifluoromethoxy-2-biphenylylmethyl group, 2'-chloro-4'-trifluoromethoxy-3-biphenylylmethyl group, 3'-methoxy-4-biphenylylmethyl group, 4'-methoxy-2-biphenylylmethyl group, 4'-methoxy-3-biphenylylmethyl group, 4'-methoxy-4-biphenylylmethyl group, 2 ' -Trifluoromethoxy-2-biphenylylmethyl group, 2'-trifluoromethoxy-3-biphenylylmethyl group, 2'-trifluoromethoxy-4-biphe Rylmethyl group, 3'-trifluoromethoxy-2-biphenylylmethyl group, 3'-trifluoromethoxy-3-biphenylylmethyl group, 3'-trifluoromethoxy-4-biphenylylmethyl group, 4'-trifluoro Methoxy-2-biphenylylmethyl group, 4'-trifluoromethoxy-3-biphenylylmethyl group, 4'-trifluoromethoxy-4-biphenylylmethyl group, 2- (4'-trifluoromethoxy-4-biphenylyl group ) Ethyl group, 3- (4'-trifluoromethoxy-4-biphenylyl) propyl group, 3- (4'-trifluoromethoxy-4-biphenylyl) propyl group, 4- (4'-trifluoromethoxy-4-) group Biphenylyl) butyl group, 5- (4'-trifluoromethoxy-4-biphenylyl) pentyl group, 6- (4'-) Biphenylyl C1-6 alkyl groups such as trifluoromethoxy-4-biphenylyl) hexyl, 4'-dimethylamino-3-biphenylylmethyl, 4'-dimethylamino-4-biphenylyl, etc. A group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group, a halogen-substituted or unsubstituted C1-6 alkoxy group and an amino group having one or two C1-6 alkyl groups as a substituent 1 to 5 groups, and preferably 1 to 3 groups selected from those groups) may be mentioned.

  As the naphthyl C1-6 alkyl group, for example, 1-naphthylmethyl group, 2-naphthylmethyl group, 2- (1-naphthyl) ethyl group, 1- (2-naphthyl) ethyl group, 3- (1-naphthyl) Propyl, 3- (2-naphthyl) propyl, 4- (1-naphthyl) butyl, 4- (2-naphthyl) butyl, 5- (1-naphthyl) pentyl, 5- (2-naphthyl) A pentyl group, 6- (1-naphthyl) hexyl group, 6- (2-naphthyl) hexyl group etc. can be mentioned.

A phenyl group (a halogen atom on a phenyl ring; a cyano group; an amino group which may have a C1-6 alkyl group as a substituent; a halogen substituted or unsubstituted C1-6 alkyl group; a halogen substituted or unsubstituted C1 -6 alkoxy group; C1-6 alkoxycarbonyl group; carboxyl group; phenoxy group [in the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group At least one of the groups selected from the group consisting of: an amino C.sub.1-6 alkyl group [a phenyl group on an amino group (a halogen atom on a phenyl ring, a halogen substituted or an unsubstituted C 1; Selected from the group consisting of an alkyl group of 6 to 6 and a halogen-substituted or unsubstituted C1-6 alkoxy group At least one group of at least one group may be substituted) and at least one group selected from the group consisting of a C1-6 alkyl group] and a phenyl C1-6 alkoxy group [on a phenyl ring At least one of a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group may be substituted As at least one of the selected groups may be substituted), for example, phenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3- Chlorophenyl group, 4-chlorophenyl group, 2-bromophenyl group, 3-bromophenyl group, 4-bromophenyl group, 2-iodophenyl group, -Iodophenyl group, 4-iodophenyl group, 2,3-difluorophenyl group, 3,4-difluorophenyl group, 3,5-difluorophenyl group, 2,4-difluorophenyl group, 2,6-difluorophenyl group 2,3-dichlorophenyl group, 3,4-dichlorophenyl group, 3,5-dichlorophenyl group, 2,4-dichlorophenyl group, 2,6-dichlorophenyl group, 3,4,5-trifluorophenyl group, 2,3 3,4,5,6-pentafluorophenyl group, 3,4,5-trichlorophenyl group, 2,4,6-trifluorophenyl group, 2,4,6-trichlorophenyl group, 2-cyanophenyl group, 3 -Cyanophenyl group, 4-cyanophenyl group, 2,4-dicyanophenyl group, 2,4,6-tricyanophenyl group, 2-methylphenyl group , 3-methylphenyl group, 4-methylphenyl group, 2,3-dimethylphenyl group, 2,4,6-trimethylphenyl group, 2-methyl-3-chlorophenyl group, 3-methyl-4-chlorophenyl group, 2 -Chloro-4-methylphenyl group, 2-methyl-3-fluorophenyl group, 2-trifluoromethylphenyl group, 3-trifluoromethylphenyl group, 4-trifluoromethylphenyl group, 2-pentafluoroethylphenyl group , 3-pentafluoroethylphenyl group, 4-pentafluoroethylphenyl group, 2-isopropylphenyl group, 3-isopropylphenyl group, 4-isopropylphenyl group, 2-tert-butylphenyl group, 3-tert-butylphenyl group , 4-tert-butylphenyl group, 2-sec-butylphenyl group, -Sec-butylphenyl group, 4-sec-butylphenyl group, 2-n-heptafluoropropylphenyl group, 3-n-heptafluoropropylphenyl group, 4-n-heptafluoropropylphenyl group, 4-pentylphenyl group , 4-hexylphenyl group, 2-methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 2,4-dimethoxyphenyl group, 2,4,6-trimethoxyphenyl group, 2-methoxy-3- Chlorophenyl group, 2-fluoro-3-methoxyphenyl group, 2-fluoro-4-methoxyphenyl group, 2,6-dimethoxyphenyl group, 2,3,4-trifluorophenyl group, 2-trifluoromethoxyphenyl group, 3-trifluoromethoxyphenyl group, 4-trifluoromethoxyphenyl group, 2-pen Fluoroethoxyphenyl group, 3-pentafluoroethoxyphenyl group, 4-pentafluoroethoxyphenyl group, 2-isopropoxyphenyl group, 3-isopropoxyphenyl group, 4-isopropoxyphenyl group, 2-tert-butoxyphenyl group, 3-tert-butoxyphenyl group, 4-tert-butoxyphenyl group, 2-sec-butoxyphenyl group, 3-sec-butoxyphenyl group, 4-sec-butoxyphenyl group, 2-n-heptafluoropropoxyphenyl group, 3-n-heptafluoropropoxyphenyl group, 4-n-heptafluoropropoxyphenyl group, 4-pentyloxyphenyl group, 4-hexyloxyphenyl group, 3-aminophenyl group, 4-methylaminophenyl group, 2-dimethyl Aminophenyl group, 3 -Dimethylaminophenyl group, 4-dimethylaminophenyl group, 2-methoxycarbonylphenyl group, 3-methoxycarbonylphenyl group, 4-methoxycarbonylphenyl group, 2-carboxyphenyl group, 3-carboxyphenyl group, 4-carboxyphenyl group Group, 2,3-dicarboxyphenyl group, 2,4,6-tricarboxyphenyl group, 2-ethoxycarbonylphenyl group, 3-ethoxycarbonylphenyl group, 4-ethoxycarbonylphenyl group, 2,3-diethoxycarbonyl group Phenyl, 2,4,6-trimethoxycarbonylphenyl, 2-phenoxyphenyl, 3-phenoxyphenyl, 4-phenoxyphenyl, 2- (2-chlorophenoxy) phenyl, 2- (3-chloro Phenoxy) phenyl group, 2- (4-) Rophenoxy) phenyl group, 3- (2-chlorophenoxy) phenyl group, 3- (3-chlorophenoxy) phenyl group, 3- (4-chlorophenoxy) phenyl group, 4- (2-chlorophenoxy) phenyl group, 4- (3-chlorophenoxy) phenyl group, 4- (4-chlorophenoxy) phenyl group, 2- (2-trifluoromethylphenoxy) phenyl group, 2- (3-trifluoromethylphenoxy) phenyl group, 2- (3-methylphenoxy) phenyl group, 2- (2,3-dimethylphenoxy) phenyl group, 2- (3,4,5-trimethylphenoxy) phenyl group, 2- (4-trifluoromethylphenoxy) phenyl group, 3- (2-trifluoromethylphenoxy) phenyl group, 3- (3-trifluoromethylphenoxy) phenyl group, -(4-Trifluoromethylphenoxy) phenyl group, 4- (2-trifluoromethylphenoxy) phenyl group, 4- (3-trifluoromethylphenoxy) phenyl group, 4- (4-trifluoromethylphenoxy) phenyl group , 2- (3-methoxyphenoxy) phenyl group, 2- (2,3-dimethoxyphenoxy) phenyl group, 2- (3,4,5-trimethoxyphenoxy) phenyl group, 2- (2-trifluoromethoxyphenoxy) ) Phenyl group, 2- (3-trifluoromethoxyphenoxy) phenyl group, 2- (4-trifluoromethoxyphenoxy) phenyl group, 3- (2-trifluoromethoxyphenoxy) phenyl group, 3- (3-trifluoro Methoxyphenoxy) phenyl group, 3- (4-trifluoromethoxyphenoxy) fe Nyl group, 4- (2-trifluoromethoxyphenoxy) phenyl group, 4- (3-trifluoromethoxyphenoxy) phenyl group, 4- (4-trifluoromethoxyphenoxy) phenyl group, 4-aminomethylphenyl group, 4 -Methylaminomethylphenyl group, 4-dimethylaminomethylphenyl group, 4-diethylaminomethylphenyl group, 4-di (n-propyl) aminomethylphenyl group, 4- (phenylaminomethyl) phenyl group, 4- (2-) Phenylaminoethyl) phenyl group, 4- (3-phenylaminopropyl) phenyl group, 4- (N-methyl-N-phenylaminomethyl) phenyl group, 4- (2-N-methyl-N-phenylaminoethyl) Phenyl, 4- (3-N-ethyl-N-phenylaminopropyl) phenyl, 4- (4 Chlorophenylaminomethyl) phenyl group, 4- [2- (4-chlorophenylamino) ethyl] phenyl group, 4- [3- (4-chlorophenylamino) propyl] phenyl group, 4- [N-methyl-N-4- 4 Chlorophenylamino] methyl] phenyl group, 4- [2- (N-methyl-N-4-chlorophenylamino) ethyl] phenyl group, 4- [3- (N-ethyl-N-4-chlorophenylamino) propyl] phenyl Group, 4- (4-trifluoromethylphenylaminomethyl) phenyl group, 4- [2- (4-trifluoromethylphenylamino) ethyl] phenyl group, 4- [2- (4-methylphenylamino) methyl] Phenyl group, 4- [2- (2,4-dimethylphenylamino) methyl] phenyl group, 4- [2- (2,4,6-trimethyl] Phenylamino) methyl] phenyl group, 4- [3- (3,5-ditrifluoromethylphenylamino) propyl] phenyl group, 4- [N-methyl-N-4-trifluoromethylphenylamino] methyl] phenyl group, 4- [2- (N-methyl-N-4-trifluoromethylphenylamino) ethyl] phenyl group, 4- [3- (N-ethyl-N-4-trifluoromethylphenylamino) propyl] phenyl group, 4- [2- (3-methoxyphenylamino) methyl] phenyl group, 4- [2- (2,4-dimethoxyphenylamino) methyl] phenyl group, 4- [2- (2,4,6-trimethoxy] Phenylamino) methyl] phenyl group, 4- (4-trifluoromethoxyphenylaminomethyl) phenyl group, 4- [2- (3,5-ditrifluoromethane) Xyphenylamino) ethyl] phenyl group, 4- [3- (4-trifluoromethoxyphenylamino) propyl] phenyl group, 4- [N-methyl-N-4-trifluoromethoxyphenylamino] methyl] phenyl group, 4- [2- (N-methyl-N-4-trifluoromethoxyphenylamino) ethyl] phenyl group, 4- [3- (N-ethyl-N-4-trifluoromethoxyphenylamino) propyl] phenyl group, 4-benzyloxyphenyl group, 4- (4-chlorobenzyloxy) phenyl group, 4- [2- (2,3-dichlorophenyl) ethoxy] phenyl group, 4- [3- (4-chlorophenyl) propoxy] phenyl group , 4- [4- (2,4,6-trichlorophenyl) butoxy] phenyl group, 4- (4-methylbenzyloxy) fe Group, 4- (3,4-dimethylbenzyloxy) phenyl group, 4- (2,4,6-trimethylbenzyloxy) phenyl group, 4- (4-trifluoromethylbenzyloxy) phenyl group, 4- [4 2- (4-trifluoromethylphenyl) ethoxy] phenyl group, 4- [3- (4-trifluoromethylphenyl) propoxy] phenyl group, 4- [4- (4-trifluoromethylphenyl) butoxy] phenyl group 4- (4-trifluoromethoxybenzyloxy) phenyl group, 4- (4-methoxybenzyloxy) phenyl group, 4- (3,4-dimethoxybenzyloxy) phenyl group, 4- (2,4,6-) Trimethoxybenzyloxy) phenyl group, 4- [2- (4-trifluoromethoxyphenyl) ethoxy] phenyl group, 4- [3- (4) Phenyl groups such as trifluoromethoxyphenyl) propoxy] phenyl group, 4- [4- (4-trifluoromethoxyphenyl) butoxy] phenyl group (a halogen atom on the phenyl ring; cyano group; C1 to 6 as a substituent Amino group which may have an alkyl group; halogen-substituted or unsubstituted C1-6 alkyl group and halogen-substituted or unsubstituted C1-6 alkoxy group; C1-6 alkoxycarbonyl group; carboxyl group; phenoxy group [on phenyl ring 1 to 5 groups, preferably 1 to 3 groups, selected from the group consisting of halogen atoms, halogen substituted or unsubstituted C.sub.1-6 alkyl groups, and halogen substituted or unsubstituted C.sub.1-6 alkoxy groups; It may be Amino C1-6 alkyl group [where the phenyl group on the amino group (on the phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group are formed; 1 to 5 groups, preferably 1 to 3 groups, may be substituted from the group; and 1 to 6 groups selected from the group consisting of C1-6 alkyl groups


It may have two or three. And phenyl C1-6 alkoxy group [in the phenyl ring, a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group is selected; Five to five, preferably one to three may be substituted. 1 to 5 and preferably 1 to 3 groups selected from the group consisting of

  Examples of the biphenylyl group (wherein at least one halogen-substituted or unsubstituted C1-6 alkyl group may be substituted on the phenyl ring) include, for example, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group , 2'-methyl-2-biphenylyl group, 2'-methyl-3-biphenylyl group, 2'-methyl-4-biphenylyl group, 3'-methyl-2-biphenylyl group, 3'-methyl-3-biphenylyl group , 3'-methyl-4-biphenylyl group, 4'-methyl-2-biphenylyl group, 4'-methyl-3-biphenylyl group, 4'-methyl-4-biphenylyl group, 3 ', 4'-dimethyl-2 -Biphenylyl group, 2 ', 4', 6'-trimethyl-3-biphenylyl group, 2'-trifluoromethyl-4 ', 6'-dimethyl-3- biphenylyl group, 2'- Trifluoromethyl-2-biphenylyl group, 2′-trifluoromethyl-3-biphenylyl group, 2′-trifluoromethyl-4-biphenylyl group, 3′-trifluoromethyl-2-biphenylyl group, 3′-trifluoro Methyl-3-biphenylyl group, 3'-trifluoromethyl-4-biphenylyl group, 4'-trifluoromethyl-2-biphenylyl group, 4'-trifluoromethyl-3-biphenylyl group, 4'-trifluoromethyl- And biphenylyl groups such as 4-biphenylyl group (1 to 3 halogen-substituted or unsubstituted C1-6 alkyl groups may be substituted on the phenyl ring).

  Examples of the amino group substituted by a C1-6 alkoxycarbonyl group include methoxycarbonylamino group, ethoxycarbonylamino group, n-propoxycarbonylamino group, isopropoxycarbonylamino group, tert-butoxycarbonylamino group, N-pentoxy Carbonylamino group, N-hexyloxycarbonylamino group, N-methyl-N-methoxycarbonylamino group, N-ethoxycarbonyl-N-methylamino group, N-methyl-N- (n-propoxycarbonyl) amino group, N -Methyl-N- (isopropoxycarbonyl) amino group, N- (tert-butoxycarbonyl) -N-methylamino group, N-methyl-N- (n-pentoxycarbonyl) amino group, N- (n-hexyl) Oxycarbonyl) -N-methylamino group, -Ethyl-N-methoxycarbonylamino group, N-ethyl-N-ethoxycarbonylamino group, N-ethyl-N- (n-propoxycarbonyl) amino group, N-ethyl-N-isopropoxycarbonylamino group, N- C1-6 alkoxy such as (tert-butoxycarbonyl) -N-ethylamino group, N-ethyl-N- (n-pentoxycarbonyl) amino group, N-ethyl-N- (n-hexyloxycarbonyl) amino group The amino group which the carbonyl group substituted (an amino group may have a C1-6 alkyl group as another substituent) can be mentioned.

  As a phenylamino group (on the phenyl ring, at least one member selected from the group consisting of a halogen atom and a halogen-substituted or unsubstituted C1-6 alkyl group may be substituted), for example, phenyl Amino group, 2-methylphenylamino group, 3-methylphenylamino group, 4-methylphenylamino group, 2-ethylphenylamino group, 3-ethylphenylamino group, 4-ethylphenylamino group, 4-propylphenylamino Group, 4-tert-butylphenylamino group, 4-butylphenylamino group, 2-trifluoromethylphenylamino group, 3-trifluoromethylphenylamino group, 4-trifluoromethylphenylamino group, 2-pentafluoroethyl Phenylamino group, 3-pentafluoroethylphenylamino group, 2 3-dimethylphenylamino group, 3,4,5-trimethylphenylamino group, 4-pentylphenylamino group, 4-hexylphenylamino group, N-phenyl-N- (2-fluorophenyl) amino group, 2-fluoro Phenylamino group, 3-fluorophenylamino group, 4-fluorophenylamino group, 2-chlorophenylamino group, 3-chlorophenylamino group, 4-chlorophenylamino group, 2-bromophenylamino group, 3-bromophenylamino group, 4-bromophenylamino group, 2-iodophenylamino group, 3-iodophenylamino group, 4-iodophenylamino group, 2,3-difluorophenylamino group, 3,4-difluorophenylamino group, 3,5- Difluorophenylamino group, 2,4-difluorophenylamino 2,6-difluorophenylamino group, 2,3-dichlorophenylamino group, 3,4-dichlorophenylamino group, 3,5-dichlorophenylamino group, 2,4-dichlorophenylamino group, 2,6-dichlorophenylamino group, 3,4,5-trifluorophenylamino group, 2,3,4,5,6-pentafluorophenylamino group, 3,4,5-trichlorophenylamino group, 2,4,6-trifluorophenylamino group An amino group having one to two phenyl groups such as 2,4,6-trichlorophenylamino group (on the phenyl ring, selected from the group consisting of a halogen atom and a halogen-substituted or unsubstituted C1-6 alkyl group; 1 to 5 groups, preferably 1 to 3 groups) may be mentioned.

  Examples of the benzoyl C1-6 alkyl group (wherein at least one halogen atom may be substituted on the phenyl ring) include, for example, benzoylmethyl group, 2-fluorobenzoylmethyl group, 3-fluorobenzoylmethyl group 4-fluorobenzoylmethyl group, 2-chlorobenzoylmethyl group, (2,3-dichlorobenzoyl) methyl group, (2,4,6-trichlorobenzoyl) methyl group, (2,3,4,5,6- Pentafluorobenzoyl) methyl group, 3-chlorobenzoylmethyl group, 4-chlorobenzoylmethyl group, 2-bromobenzoylmethyl group, 3-bromobenzoylmethyl group, 4-bromobenzoylmethyl group, 2-benzoylethyl group, 2- (2-fluorobenzoyl) ethyl group, 2- (3-fluorobenzoyl) ethyl group, 2- 4-fluorobenzoyl) ethyl group, 2- (2-chlorobenzoyl) ethyl group, 2- (3-chlorobenzoyl) ethyl group, 2- (4-chlorobenzoyl) ethyl group, 3- (2-chlorobenzoyl) propyl Group, 3- (3-chlorobenzoyl) propyl group, 3- (4-chlorobenzoyl) propyl group, 4- (2-chlorobenzoyl) butyl group, 4- (3-chlorobenzoyl) butyl group, 4- (4) -Chlorobenzoyl) butyl group, 5- (2-chlorobenzoyl) pentyl group, 5- (3-chlorobenzoyl) pentyl group, 5- (4-chlorobenzoyl) pentyl group, 6- (2-chlorobenzoyl) hexyl group Benzoyl C1-6 alkyl groups such as 6- (3-chlorobenzoyl) hexyl group, 6- (4-chlorobenzoyl) hexyl group, etc. (phenyl The upper may have one to five halogen atoms as a substituent.) May be mentioned.

  Examples of the phenylcarbamoyl C1-6 alkyl group (wherein at least one halogen-substituted or unsubstituted C1-6 alkyl group may be substituted on the phenyl ring) include, for example, phenylcarbamoylmethyl group, 2-methylphenyl A carbamoylmethyl group, a 3-methylphenylcarbamoylmethyl group, a 4-methylphenylcarbamoylmethyl group, a 2,3-dimethylphenylcarbamoylmethyl group, a 2,4-dimethylphenylcarbamoylmethyl group, a 2,6-dimethylphenylcarbamoylmethyl group, 2,4,6-trimethylphenylcarbamoylmethyl group, 2-trifluoromethylphenylcarbamoylmethyl group, 3-trifluoromethylphenylcarbamoylmethyl group, 4-trifluoromethylphenylcarbamoylmethyl group, 2,3-dito Fluoromethylphenylcarbamoylmethyl group, 2,4-ditrifluoromethylphenylcarbamoylmethyl group, 2,6-ditrifluoromethylphenylcarbamoylmethyl group, 2-pentafluoroethylphenylcarbamoylmethyl group, 3-pentafluoroethylphenylcarbamoylmethyl group 4-pentafluoroethylphenylcarbamoylmethyl group, 2- (n-propylphenyl) carbamoylmethyl group, 3- (n-propylphenyl) carbamoylmethyl group, 4- (n-propylphenyl) carbamoylmethyl group, 2- ( Phenylcarbamoyl) ethyl group, 2- (3-trifluoromethylphenylcarbamoyl) ethyl group, 2- (4-trifluoromethylphenylcarbamoyl) ethyl group, 2- (2,3-ditrifluoromethyl) Phenylcarbamoyl) ethyl group, 2- (2,4-ditrifluoromethylphenylcarbamoyl) ethyl group, 2- (2,6-ditrifluoromethylphenylcarbamoyl) ethyl group, 2- (2-pentafluoroethylphenylcarbamoyl) ethyl Group, 2- (3-pentafluoroethylphenylcarbamoyl) ethyl group, 2- (4-pentafluoroethylphenylcarbamoyl) ethyl group, 3- (phenylcarbamoyl) propyl group, 3- (3-trifluoromethylphenylcarbamoyl) Propyl group, 3- (4-trifluoromethylphenylcarbamoyl) propyl group, 3- (2,3-ditrifluoromethylphenylcarbamoyl) propyl group, 3- (2,4-ditrifluoromethylphenylcarbamoyl) propyl group, 3 -(2,6-Jito Trifluoromethylphenylcarbamoyl) propyl group, 3- (2-pentafluoroethylphenylcarbamoyl) propyl group, 3- (3-pentafluoroethylphenylcarbamoyl) propyl group, 3- (4-pentafluoroethylphenylcarbamoyl) propyl group Phenylcarbamoyl C1-6 alkyl such as 4- (4-trifluoromethylphenylcarbamoyl) butyl group, 5- (4-trifluoromethylphenylcarbamoyl) pentyl group, 6- (4-trifluoromethylphenylcarbamoyl) hexyl group, etc. Mention may be made of the group (on the phenyl ring, 1 to 3 halogen-substituted or unsubstituted C1-6 alkyl groups may be substituted).

  As a thiazolyl C1-6 alkyl group (wherein at least one group selected from the group consisting of a halogen-substituted or unsubstituted phenyl group and a C1-6 alkyl group may be substituted on the thiazole ring), For example, 4-thiazolylmethyl group, 5-thiazolylmethyl group, 2-methyl-4-thiazolylmethyl group, 2-methyl-5-thiazolylmethyl group, 2,5-dimethyl-4-thiazolylmethyl group, 2,4-dimethyl-5-thiazolylmethyl Group, 2-methyl-5-phenyl-4-thiazolylmethyl group, 2-methyl-4-phenyl-5-thiazolylmethyl group, 2-phenyl-4-thiazolylmethyl group, 2-phenyl-5-thiazolylmethyl group, 2-phenyl- 5-methyl-4-thiazolylmethyl group, 2-phenyl-4-methyl-5-thiazolylmethyl 2-methyl-5- (2-fluorophenyl) -4-thiazolylmethyl group, 2-methyl-4- (2-fluorophenyl) -5-thiazolylmethyl group, 2- (2-chlorophenyl) -4-thiazolylmethyl group, 2- (2-bromophenyl) -5-thiazolylmethyl group, 2- (2-fluorophenyl) -5-methyl-4-thiazolylmethyl group, 2- (2-fluorophenyl) -4-methyl-5-thiazolylmethyl group, 2-methyl-5- (3-iodophenyl) -4-thiazolylmethyl group, 2-methyl-4- (3-fluorophenyl) -5-thiazolylmethyl group, 2- (2,3-difluorophenyl) -4-thiazolylmethyl Group, 2- (3-fluorophenyl) -5-thiazolylmethyl group, 2- (3-fluorophenyl) -5-methyl-4-thia Rylmethyl, 2- (3-fluorophenyl) -4-methyl-5-thiazolylmethyl, 2-methyl-5- (2,4,6-trichlorophenyl) -4-thiazolylmethyl, 2-methyl-4- ( 2,3,4,5,6-pentafluorophenyl) -5-thiazolylmethyl group, 2- (4-fluorophenyl) -4-thiazolylmethyl group, 4- (2-fluorophenyl) -5-thiazolylmethyl group, 2- (4-fluorophenyl) -5-methyl-4-thiazolylmethyl group, 2- (4-fluorophenyl) -4-methyl-5-thiazolylmethyl group, 2-methyl-5- (2-chlorophenyl) -4-thiazolylmethyl group , 2-methyl-4- (2-chlorophenyl) -5-thiazolylmethyl group, 2- (2-chlorophenyl) -4-thiazolylmethyl group, 2 -(2-chlorophenyl) -5-thiazolylmethyl group, 2- (2-chlorophenyl) -5-methyl-4-thiazolylmethyl group, 2- (2-chlorophenyl) -4-methyl-5-thiazolylmethyl group, 2-methyl- 5- (3-chlorophenyl) -4-thiazolylmethyl group, 2-methyl-4- (3-chlorophenyl) -5-thiazolylmethyl group, 2- (3-chlorophenyl) -4-thiazolylmethyl group, 2- (2-fluorophenyl) ) 5-thiazolylmethyl group, 2- (3-chlorophenyl) -5-methyl-4-thiazolylmethyl group, 2- (3-chlorophenyl) -4-methyl-5-thiazolylmethyl group, 2-methyl-5- (4-) Chlorophenyl) -4-thiazolylmethyl group, 2-methyl-4- (4-chlorophenyl) -5-thiazolylmethyl group 2- (4-chlorophenyl) -4-thiazolylmethyl group, 2- (4-chlorophenyl) -5-thiazolylmethyl group, 2- (4-chlorophenyl) -5-methyl-4-thiazolylmethyl group, 2- (4-chlorophenyl) group -4-methyl-5-thiazolylmethyl group, 2- (2-thiazolyl) ethyl group, 2- (4-thiazolyl) ethyl group, 2- (5-thiazolyl) ethyl group, 2- (2-methyl-4-thiazolyl) ) Ethyl group, 2- (2-methyl-5-thiazolyl) ethyl group, 2- (2,5-dimethyl-4-thiazolyl) ethyl group, 2- (2,4-dimethyl-5-thiazolyl) ethyl group, 2- (2-methyl-5-phenyl-4-thiazolyl) ethyl group, 2- (2-methyl-4-phenyl-5-thiazolyl) ethyl group, 2- (2-phenyl-4-thiazole) ) Ethyl group, 2- (2-phenyl-5-thiazolyl) ethyl group, 2- (2-phenyl-5-methyl-4-thiazolyl) ethyl group, 3- (2-thiazolyl) propyl group, 2- (4) -Thiazolyl) propyl group, 3- (5-thiazolyl) propyl group, 3- (2-methyl-4-thiazolyl) propyl group, 2- (2-methyl-5-thiazolyl) propyl group, 3- (2,5) -Dimethyl-4-thiazolyl) propyl, 3- (2,4-dimethyl-5-thiazolyl) propyl, 3- (2-methyl-5-phenyl-4-thiazolyl) propyl, 3- (2-methyl) -4-phenyl-5-thiazolyl) propyl, 2- (2-phenyl-4-thiazolyl) propyl, 3- (3-phenyl-5-thiazolyl) propyl, 3- (2-phenyl-5-methyl) -4- Thiazolyl) propyl group, 4- (2-thiazolyl) butyl group, 4- (4-thiazolyl) butyl group, 3- (5-thiazolyl) butyl group, 4- (2-methyl-4-thiazolyl) butyl group, 4 -(2-methyl-5-thiazolyl) butyl group, 4- (2,5-dimethyl-4-thiazolyl) butyl group, 4- (2,4-dimethyl-5-thiazolyl) butyl group, 4- (2- Methyl-5-phenyl-4-thiazolyl) butyl group, 4- (2-methyl-4-phenyl-5-thiazolyl) butyl group, 4- (2-phenyl-4-thiazolyl) butyl group, 4-phenyl-5 -Thiazolyl) butyl group, 4- (2-phenyl-5-methyl-4-thiazolyl) butyl group, 5- (2-thiazolyl) pentyl group, 5- (4-thiazolyl) pentyl group, 5- (5-thiazolyl) group ) Pentyl 5- (2-methyl-4-thiazolyl) pentyl group, 5- (2-methyl-5-thiazolyl) pentyl group, 5- (2,5-dimethyl-4-thiazolyl) pentyl group, 5- (2, 4-dimethyl-5-thiazolyl) pentyl group, 5- (2-methyl-5-phenyl-4-thiazolyl) pentyl group, 5- (2-methyl-4-phenyl-5-thiazolyl) pentyl group, 5- (5-methyl-2-phenyl-5-thiazolyl) pentyl group 2-phenyl-4-thiazolyl) pentyl group, 5- (4-phenyl-5-thiazolyl) pentyl group, 5- (2-phenyl-5-methyl-4-thiazolyl) pentyl group, 5- (2-thiazolyl) group Hexyl, 5- (4-thiazolyl) hexyl, 5- (5-thiazolyl) hexyl, 5- (2-methyl-4-thiazolyl) hexyl, 5- (2-methyl-5-thiazolyl) hexyl , 5- (2,5-dimethyl-4-thiazolyl) hexyl group, 5- (2,4-dimethyl-5-thiazolyl) hexyl group, 5- (2-methyl-5-phenyl-4-thiazolyl) hexyl group 5- (2-Methyl-4-phenyl-5-thiazolyl) hexyl group, 5- (2-phenyl-4-thiazolyl) hexyl group, 4-phenyl-5-thiazolyl) hexyl group, 5- (2-phenyl) group A thiazolyl C1-6 alkyl group such as a -5-methyl-4-thiazolyl hexyl group (on the thiazole ring, a group selected from the group consisting of a halogen-substituted or unsubstituted phenyl group and a C1-6 alkyl group is To 2) may be mentioned.

  As an oxazolyl C1-6 alkyl group (On the oxazole ring, at least one of a group selected from the group consisting of a halogen-substituted or unsubstituted phenyl group and a C1-6 alkyl group may be substituted), For example, 4-oxazolylmethyl group, 5-oxazolylmethyl group, 2-methyl-4-oxazolylmethyl group, 2-methyl-5-oxazolylmethyl group, 2,5-dimethyl-4- Oxazolylmethyl group, 2,5-diphenyl-4-oxazolylmethyl group, 2,4-dimethyl-5-oxazolylmethyl group, 2-methyl-5-phenyl-4-oxazolylmethyl group, 2-methyl-4-phenyl-5-oxazolylmethyl group, 2-phenyl-4-oxazolylmethyl group, 2-phenyl-5-oxazolylmethyl group, 2-phenyl-5-methyl- -Oxazolylmethyl group, 2-phenyl-4-methyl-5-oxazolylmethyl group, 2-methyl-5- (2,3,4,5,6-pentafluorophenyl) -4-oxazolyl Methyl group, 2-methyl-4- (2-fluorophenyl) -5-oxazolylmethyl group, 2- (2,4-difluorophenyl) -4-oxazolylmethyl group, 2- (2-fluorophenyl) ) 5-oxazolylmethyl group, 2- (2-fluorophenyl) -5-methyl-4-oxazolylmethyl group, 2- (2-fluorophenyl) -4-methyl-5-oxazolylmethyl Group, 2-methyl-5- (3-fluorophenyl) -4-oxazolylmethyl group, 2-methyl-4- (3-fluorophenyl) -5-oxazolylmethyl group, 2- (3-fluoro) Phenyl) -4-oxa Rylmethyl group, 2- (3-fluorophenyl) -5-oxazolylmethyl group, 2- (3-fluorophenyl) -5-methyl-4-oxazolylmethyl group, 2- (3-fluorophenyl)- 4-methyl-5-oxazolylmethyl group, 2-methyl-5- (4-fluorophenyl) -4-oxazolylmethyl group, 2-methyl-4- (4-fluorophenyl) -5-oxazole Methyl group, 2- (4-fluorophenyl) -4-oxazolylmethyl group, 2- (4-fluorophenyl) -5-oxazolylmethyl group, 2- (4-fluorophenyl) -5-methyl -4-oxazolyl methyl group, 2- (4-bromophenyl) -4-methyl-5-oxazolyl methyl group, 2-methyl-5- (2-chlorophenyl) -4-oxazolyl methyl group, 2-Methyl- 4- (2-chlorophenyl) -5-oxazolylmethyl group, 2- (2-chlorophenyl) -4-oxazolylmethyl group, 2- (2-iodophenyl) -5-oxazolylmethyl group, 2 -(2-chlorophenyl) -5-methyl-4-oxazolylmethyl group, 2- (2-chlorophenyl) -4-methyl-5-oxazolylmethyl group, 2-methyl-5- (3-chlorophenyl) group 4-oxazolyl methyl group, 2-methyl-4- (3-chlorophenyl) -5-oxazolyl methyl group, 2- (3-chlorophenyl) -4-oxazolyl methyl group, 2- (2, 4.6-trichlorophenyl) -5-oxazolylmethyl group, 2- (3-chlorophenyl) -5-methyl-4-oxazolylmethyl group, 2- (3-chlorophenyl) -4-methyl-5- Oxazol Methyl group, 2-methyl-5- (4-chlorophenyl) -4-oxazolylmethyl group, 2-methyl-4- (4-chlorophenyl) -5-oxazolylmethyl group, 2- (4-chlorophenyl) group 4-oxazolyl methyl group, 2- (4-chlorophenyl) -5-oxazolyl methyl group, 2- (4-chlorophenyl) -5-methyl-4-oxazolyl methyl group, 2- (4- Chlorophenyl) -4-methyl-5-oxazolylmethyl group, 2- (4-oxazolyl) ethyl group, 2- (5-oxazolyl) ethyl group, 2- (2-methyl-4-oxazolyl) ethyl group, 2 -(2-Methyl-5-oxazolyl) ethyl group, 2- (2-phenyl-5-methyl-4-oxazolyl) ethyl group, 2- [2- (4-chlorophenyl) -5-methyl-4-oxazolyl Ethyl group, 3- (4-oxazolyl) propyl group, 3- (5-oxazolyl) propyl group, 3- (2-methyl-4-oxazolyl) propyl group, 3- (2-methyl-5-oxazolyl) propyl group , 3- (2-phenyl-5-methyl-4-oxazolyl) propyl group, 3- [2- (4-chlorophenyl) -5-methyl-4-oxazolyl] propyl group, 4- (4-oxazolyl) butyl group 4- (5-oxazolyl) butyl group, 4- (2-methyl-4-oxazolyl) butyl group, 4- (2-methyl-5-oxazolyl) butyl group, 4- (2-phenyl-5-methyl-) 4-oxazolyl) butyl group, 4- [2- (4-chlorophenyl) -5-methyl-4-oxazolyl] butyl group, 5- (4-oxazolyl) pentyl group, 5- (5-oxazolyl) group Pentyl), 5- (2-methyl-4-oxazolyl) pentyl, 5- (2-methyl-5-oxazolyl) pentyl, 5- (2-phenyl-5-methyl-4-oxazolyl) pentyl , 5- [2- (4-chlorophenyl) -5-methyl-4-oxazolyl] pentyl group, 6- (4-oxazolyl) hexyl group, 6- (5-oxazolyl) hexyl group, 6- (2-methyl-) 4-oxazolyl) hexyl group, 6- (2-methyl-5-oxazolyl) hexyl group, 6- (2-phenyl-5-methyl-4-oxazolyl) hexyl group, 6- [2- (4-chlorophenyl)- Oxazolyl C1-6 alkyl groups such as 6-methyl-4-oxazolyl] hexyl group (on the oxazole ring, halogen substituted or unsubstituted phenyl group and C1-6 alkyl Groups selected from the group consisting of Le group can be mentioned may) be in one or two substituents.

  As the indolyl C1-6 alkyl group, for example, indoline-1-ylmethyl group, indoline-2-ylmethyl group, indoline-3-ylmethyl group, indoline-4-ylmethyl group, indoline-5-ylmethyl group, indoline-6-yl group Ylmethyl group, indoline-7-ylmethyl group, 2- (indoline-3-yl) ethyl group, 3- (indoline-3-yl) propyl group, 4- (indoline-3-yl) butyl group, 5- (indoline) -3-yl) pentyl group, 6- (indoline-3-yl) hexyl group, 2- (indoline-4-yl) ethyl group, 3- (indoline-4-yl) propyl group, 4- (indoline-4) -Yl) butyl group, 5- (indoline-4-yl) pentyl group, 6- (indoline-4-yl) hexyl group, 2- (indoline- -Yl) ethyl group, 3- (indoline-5-yl) propyl group, 4- (indoline-5-yl) butyl group, 5- (indoline-5-yl) pentyl group, 6- (indoline-5-yl) group ) Hexyl group, 2- (indoline-6-yl) ethyl group, 3- (indoline-6-yl) propyl group, 4- (indoline-6-yl) butyl group, 5- (indoline-6-yl) pentyl Group, 6- (indoline-6-yl) hexyl group, 2- (indoline-7-yl) ethyl group, 3- (indoline-7-yl) propyl group, 4- (indoline-7-yl) butyl group, 5- (indoline-7-yl) pentyl group, 6- (indoline-7-yl) hexyl group and the like can be mentioned.

  Examples of the furyl C1-6 alkyl group (on the furan ring, at least one halogen-substituted or unsubstituted phenyl group may be substituted) include, for example, 2-furylmethyl group, 1- (3-furyl) Ethyl group, 2- (2-furyl) ethyl group, 3- (3-furyl) propyl group, 4- (3-furyl) butyl group, 5- (2-furyl) pentyl group, 6- (2-furyl) Hexyl group, 2-methyl-3- (3-furyl) propyl group, 1,1-dimethyl-2- (2-furyl) ethyl group, 3,4-diphenyl-2-furylmethyl group, 3,4,5 -Triphenyl-2-furylmethyl group, 5-phenyl-2-furylmethyl group, 5- (2-fluorophenyl) -2-furylmethyl group, 5- (3-fluorophenyl) -2-furylmethyl group, 5- (4-fluorophenyl)- -Furyl methyl group, 5- (2-chlorophenyl) -2-furyl methyl group, 5- (3-chlorophenyl) -2-furyl methyl group, 5- (4-chlorophenyl) -2-furyl methyl group, 5- ( 2-bromophenyl) -2-furylmethyl group, 5- (3-bromophenyl) -2-furylmethyl group, 5- (4-bromophenyl) -2-furylmethyl group, 4-phenyl-2-furylmethyl Group, 4- (2,3,4,5,6-pentafluorophenyl) -2-furylmethyl group, 4- (3,4-difluorophenyl) -2-furylmethyl group, 4- (4-iodophenyl) ) 2-Furylmethyl group, 4- (2,3-dichlorophenyl) -2-furylmethyl group, 4- (3-chlorophenyl) -2-furylmethyl group, 4- (2,4,6-trichlorophenyl) -2-f Methyl group, 4- (2-bromophenyl) -2-furylmethyl group, 4- (3-bromophenyl) -2-furylmethyl group, 4- (4-bromophenyl) -2-furylmethyl group, 5- Phenyl-2-furylmethyl group, 2- (2-furyl) ethyl group, 3- (2-furyl) propyl group, 4- (2-furyl) butyl group, 5- (2-furyl) pentyl group, 6- (2-furyl) hexyl group, 2- [5- (4-chlorophenyl) -2-furyl] ethyl group, 3- [5- (4-chlorophenyl) -2-furyl] propyl group, 4- [5- (5-furyl) hexyl group; Furyl C1-6 alkyl group (furan ring such as 4-chlorophenyl) -2-furyl] butyl group, 5- (2-furyl) pentyl group, 6- [5- (4-chlorophenyl) -2-furyl] hexyl group, etc. Above, halogen substituted or unsubstituted The phenyl group may be substituted by 1 to 3).

  The imidazolyl C1-6 alkyl group (a phenyl group may be substituted on the imidazole ring) is, for example, 4-imidazolylmethyl group, 2- (4-imidazolyl) ethyl group, 3- (2-imidazolyl group) ) Propyl group, 4- (1-imidazolyl) butyl group, 5- (5-imidazolyl) pentyl group, 6- (4-imidazolyl) hexyl group, 2,5-diphenyl-1-imidazolylmethyl group, 2-phenyl- 4-imidazolyl methyl group, 2- (2-phenyl-4-imidazolyl) ethyl group, 3- (2-phenyl-4-imidazolyl) propyl group, 4- (2-phenyl-5-imidazolyl) butyl group, 5- Imidazolyl C1-6 alkyl such as (2-phenyl-4-imidazolyl) pentyl, 6- (2-phenyl-4-imidazolyl) hexyl and the like (On the imidazole ring, a phenyl group may be one to two substituents) group and the like.

  As the quinolyl C1-6 alkyl group, for example, 4-quinolylmethyl group, 2- (4-quinolyl) ethyl group, 3- (4-quinolyl) propyl group, 4- (4-quinolyl) butyl group, 5- (4) -Quinolyl) pentyl, 6- (4-quinolyl) hexyl, 5-quinolylmethyl, 2- (5-quinolyl) ethyl, 3- (5-quinolyl) propyl, 4- (5-quinolyl) butyl , 5- (5-quinolyl) pentyl group, 6- (5-quinolyl) hexyl group, 6-quinolylmethyl group, 2- (6-quinolyl) ethyl group, 3- (6-quinolyl) propyl group, 4- (6 -Quinolyl) butyl group, 5- (6-quinolyl) pentyl group, 6- (6-quinolyl) hexyl group, 7-quinolylmethyl group, 2- (7-quinolyl) ethyl group, 3- (7-quinolyl) propyl group , 4- 7-quinolyl) butyl group, 5- (7-quinolyl) pentyl group, 6- (7-quinolyl) hexyl group, 8-quinolylmethyl group, 2- (8-quinolyl) ethyl group, 3- (8-quinolyl) propyl And 4- (8-quinolyl) butyl, 5- (8-quinolyl) pentyl, 6- (8-quinolyl) hexyl and the like.

  Examples of the tetrazolyl group (a phenyl group may be substituted on the tetrazole ring) include, for example, 5- (1H) -tetrazolyl group, 1-phenyl-5- (1H) -tetrazolyl group, etc. Be

  The pyrimidyl group which may be substituted by a phenyl group is, for example, 2-pyrimidyl group, 3-pyrimidyl group, 4-pyrimidyl group, 4-phenyl-2-pyrimidyl group, 2-phenyl-4-pyrimidyl group, 4 And 6-diphenyl-2-pyrimidinyl groups.

  As the benzoxazolyl group, for example, 2-benzoxazolyl group, 4-benzoxazolyl group, 5-benzoxazolyl group, 6-benzoxazolyl group, 7-benzoxazolyl group, etc. Can be mentioned.

  As the benzothiazolyl group, for example, benzothiazol-2-yl group, benzothiazol-4-yl group, benzothiazol-5-yl group, benzothiazol-6-yl group, benzothiazol-7-yl group And the like.

  Examples of phenoxy C2-6 alkanoyl group which may have a halogen atom substituted on the phenyl ring include phenoxy acetyl group, 3-phenoxy propionyl group, 4-phenoxy butyryl group, 5-phenoxy pentanoyl group, 6- Phenoxyhexanoyl group, 4- (4-chlorophenoxy) butyryl group, 5- (4-chlorophenoxy) pentanoyl group, 6- (4-chlorophenoxy) hexanoyl group, 2-fluorophenoxyacetyl group, 3-fluorophenoxyacetyl group Group, 4-fluorophenoxyacetyl group, 2-chlorophenoxyacetyl group, 3-chlorophenoxyacetyl group, 4-chlorophenoxyacetyl group, 4-bromophenoxyacetyl group, 2,3-difluorophenoxyacetyl group, 2-fluoro- 4-chlorophenoxy A cetyl group, 3,5-difluorophenoxyacetyl group, 2,3,4,5,6-pentafluorophenoxyacetyl group, 2,4,6-trichlorophenoxyacetyl group, 3- (2-fluorophenoxy) propionyl group, 3- (3-fluorophenoxy) propionyl group, 3- (4-fluorophenoxy) propionyl group, 3- (2-chlorophenoxy) propionyl group, 3- (3-chlorophenoxy) propionyl group, 3- (4-chloro) Phenoxy) propionyl group, 3- (4-bromophenoxy) propionyl group, 3- (2,3-difluorophenoxy) propionyl group, 3- (2-fluoro-4-chlorophenoxy) propionyl group, 3- (3,5 1 to 5 halogens substituted on phenyl ring such as -difluorophenoxy) propionyl group Which may be phenoxy C2~6 alkanoyl group and the like.

  The phenylthio C2-6 alkanoyl group which may be substituted by a halogen atom on the phenyl ring is a group composed of a substituted or unsubstituted phenylthio group having 1 to 5 halogen atoms or a C1-6 alkanoyl group, For example, phenylthioacetyl group, 3-phenylthiopropionyl group, 4-phenylthiobutyryl group, 5-phenylthiopentanoyl group, 6-phenylthiohexanoyl group, 4- (4-chlorophenyl) thiobutyryl group, 5 -(4-chlorophenyl) thiopentanoyl group, 6- (4-chlorophenyl) thiohexanoyl group, 2-fluorophenylthioacetyl group, 3-fluorophenylthioacetyl group, 4-fluorophenylthioacetyl group, 2-chlorophenylthioacetyl group, 2,4-dichlorophenylthioacetyl group, , 4,6-trichlorophenylthioacetyl group, 2,3,4,5,6-tetrafluorophenylthioacetyl group, 3-chlorophenylthioacetyl group, 4-chlorophenylthioacetyl group, 4-bromophenylthioacetyl group, 2,3-Difluorophenylthioacetyl group, 2-fluoro-4-chlorophenylthioacetyl group, 3,5-difluorophenylthioacetyl group, 3- (2-fluorophenyl) thiopropionyl group, 3- (3-fluorophenyl) ) Thiopropionyl group, 3- (4-fluorophenyl) thiopropionyl group, 3- (2-chlorophenyl) thiopropionyl group, 3- (3-chlorophenyl) thiopropionyl group, 3- (4-chlorophenyl) thiopropionyl group, 3- (4-bromophenyl) thiopropionyl group, - (2,3-difluorophenyl) thiopropionyl group, 3- (2-fluoro-4-chlorophenyl) thiopropionyl group, and a 3- (3,5-difluorophenyl) thiopropionyl group or the like.

  A benzoyl group (a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group, a halogen-substituted or unsubstituted C1-6 alkoxy group and a C1-6 alkyl group as a substituent group on the phenyl ring As the group consisting of at least one group selected from the group consisting of: benzoyl group, 2-fluorobenzoyl group, 3-fluorobenzoyl group, 4-fluorobenzoyl group, 2,3- Difluorobenzoyl group, 3,4-difluorobenzoyl group, 2-chlorobenzoyl group, 3-chlorobenzoyl group, 4-chlorobenzoyl group, 2,3-dichlorobenzoyl group, 3,4-dichlorobenzoyl group, 2,4, 6-trichlorobenzoyl group, 4-iodobenzoyl group, 2,3,4,5,6-tetrafluoroben , 2-bromobenzoyl group, 3-bromobenzoyl group, 4-bromobenzoyl group, 2,3-dibromobenzoyl group, 3,4-dibromobenzoyl group, 2-methylbenzoyl group, 3-methylbenzoyl group, 4 -Methylbenzoyl group, 2,3-dimethylbenzoyl group, 3,4-dimethylbenzoyl group, 3,4,5-trimethylbenzoyl group, 2-trifluoromethylbenzoyl group, 3-trifluoromethylbenzoyl group, 4-trimethylbenzoyl group Fluoromethylbenzoyl group, 2,3-ditrifluoromethylbenzoyl group, 3,4-ditrifluoromethylbenzoyl group, 2-methoxybenzoyl group, 3-methoxybenzoyl group, 4-methoxybenzoyl group, 3,4-dimethoxybenzoyl group 2,4,6-trimethoxybenzoyl group, 2-trifluoro Toxibenzoyl group, 3-trifluoromethoxybenzoyl group, 4-trifluoromethoxybenzoyl group, 2-aminobenzoyl group, 3-aminobenzoyl group, 4-aminobenzoyl group, 2-methylaminobenzoyl group, 3-methylaminobenzoyl group Group, 4-methylaminobenzoyl group, 2-ethylaminobenzoyl group, 3-ethylaminobenzoyl group, 4-ethylaminobenzoyl group, 2-propylaminobenzoyl group, 3-propylaminobenzoyl group, 4-propylaminobenzoyl group , 4-butylaminobenzoyl group, 4-pentylaminobenzoyl group, 4-hexylaminobenzoyl group, 2-dimethylaminobenzoyl group, 3-dimethylaminobenzoyl group, 4-dimethylaminobenzoyl group, 2-diethylaminobenzoyl group, 3-diethylaminobenzoyl group, 4-diethylaminobenzoyl group, 2-dipropylaminobenzoyl group, 3-dipropylaminobenzoyl group, 4-dipropylaminobenzoyl group, 4-dibutylaminobenzoyl group, 4-dipentylaminobenzoyl group, Benzoyl groups such as 4-dihexylaminobenzoyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group, a halogen substituted or unsubstituted C1-6 alkoxy group and a C1-6 alkyl as a substituent 1 to 5, preferably 1 to 3 groups selected from the group consisting of amino groups which may have 1 to 2 groups may be mentioned.

  As a biphenylyl carbonyl group, 2-biphenylyl carbonyl group, 3-biphenylyl carbonyl group, 4-biphenylyl carbonyl group etc. are mentioned, for example.

  As a pyridyl carbonyl group, 2-pyridyl carbonyl group, 3-pyridyl carbonyl group, 4-pyridyl carbonyl group etc. are mentioned, for example.

  Examples of the phenyl C2-6 alkenylcarbonyl group which may be substituted by a halogen atom on the phenyl ring include, for example, 3-phenyl-2-propenylcarbonyl group (conventional name: cinnamoyl group), 4-phenyl-2-butenyl Carbonyl group, 4-phenyl-3-butenylcarbonyl group, 5-phenyl-2-pentenylcarbonyl group, 5-phenyl-4-pentenylcarbonyl group, 5-phenyl-3-pentenylcarbonyl group, 6-phenyl-5-carbonyl group Hexenylcarbonyl group, 6-phenyl-4-pentenylcarbonyl group, 6-phenyl-3-hexenyloxycarbonyl group, 4-phenyl-1,3-butadienylcarbonyl group, 6-phenyl-1,3,5-hexacene Trienylcarbonyl group, 3- (2-fluorophenyl) -2-propenylcarbonyl (Also referred to as 2-fluorocinnamoyl group in the common name), 3- (3-fluorophenyl) -2-propenylcarbonyl group, 3- (4-fluorophenyl) -2-propenylcarbonyl group, 2,4 -Difluorocinnamoyl group, 3- (2,5-difluorophenyl) -2-propenylcarbonyl group, 3- (3,5-difluorophenyl) -2-propenylcarbonyl group, 3- (3,4-difluorophenyl) group -2-propenyl carbonyl group, 3- (2,3,4,5,6-pentafluorophenyl) -2-propenyl carbonyl group, 3- (2-chlorophenyl) -2-propenyl carbonyl group, 3- ( 3-chlorophenyl) -2-propenylcarbonyl group, 3- (4-chlorophenyl) -2-propenylcarbonyl group, 3- (2,4 Dichlorophenyl) -2-propenylcarbonyl group, 3- (2,5-dichlorophenyl) -2-propenylcarbonyl group, 3- (3,5-dichlorophenyl) -2-propenylcarbonyl group, 3- (3,4-dichlorophenyl) ) -2-propenyl carbonyl group, 3- (2,4,6-trichlorophenyl) -2-propenyl carbonyl group, 3- (2-bromophenyl) -2-propenyl carbonyl group, 3- (3- (3-) Bromophenyl) -2-propenylcarbonyl group, 3- (4-bromophenyl) -2-propenylcarbonyl group, 3- (2,4-dibromophenyl) -2-propenylcarbonyl group, 3- (2,5- Dibromophenyl) -2-propenylcarbonyl group, 3- (3,5-dibromophenyl) -2-propenylcarbonyl group, Mention may be made of a phenyl C2-6 alkenyl carbonyl group which may be substituted by 1 to 5 halogen atoms on the phenyl ring such as 3- (3,4-dibromophenyl) -2-propenyl carbonyl group.

  The phenyl C1-6 alkylsulfonyl group which the halogen atom may substitute on the phenyl ring means a phenyl C1-6 alkyl group and a sulfonyl which may be substituted by 1 to 5 halogens on the phenyl ring defined above A phenylsulfonyl group, a phenethylsulfonyl group, 3-phenylpropylsulfonyl group, 4-phenylbutylsulfonyl group, 5-phenylpentylsulfonyl group, 6-phenylhexylsulfonyl group, 2- Fluorobenzylsulfonyl group, 3-fluorobenzylsulfonyl group, 4-fluorobenzylsulfonyl group, 2-chlorobenzylsulfonyl group, 3-chlorobenzylsulfonyl group, 4-chlorobenzylsulfonyl group, 2,3-dichlorobenzylsulfonyl group, 3 , 4-Dichlorobenzyls Phonyl group, 3,5-dichlorobenzylsulfonyl group, 2,4-dichlorobenzylsulfonyl group, 3,4,5-trifluorobenzylsulfonyl group, 2,3,4,5,6-pentafluorobenzylsulfonyl group, 2 -(2-fluoro) phenethylsulfonyl group, 2- (3-fluoro) phenethylsulfonyl group, 2- (4-fluoro) phenethylsulfonyl group, 2- (2-chloro) phenethylsulfonyl group, 2- (3-chloro) group Phenethylsulfonyl group, 2- (4-chloro) phenethylsulfonyl group, 2- (2,3-dichloro) phenethylsulfonyl group, 2- (3,4-dichloro) phenethylsulfonyl group, 2- (3,5-dichloro) Phenethylsulfonyl group, 2- (2,4-dichloro) phenethylsulfonyl group 2- (3,4,5- trifluoro) ) Phenethylsulfonyl group, 3- (2-fluorophenyl) propylsulfonyl group, 3- (3-fluorophenyl) propylsulfonyl group, 3- (4-fluorophenyl) propylsulfonyl group, 3- (2-chlorophenyl) propylsulfonyl Group, 3- (3-chlorophenyl) propylsulfonyl group, 3- (4-chlorophenylprosulfonyl group, 2- (2,3-dichlorophenyl) propylsulfonyl group, 3- (3,4-dichlorophenyl) propylsulfonyl group, 3 Examples include-(3,5-dichlorophenyl) propylsulfonyl group, 3- (2,4-dichlorophenyl) propylsulfonyl group, 3- (3,4,5-trifluorophenyl) propylsulfonyl group and the like.

  As a halogen substituted or unsubstituted C1-8 alkyl group, for example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, n- Pentyl group, neopentyl group, 3-methylpentyl group, n-hexyl group, isohexyl group, 1,3,5-trimethylhexyl group, n-heptyl group, 6-methylheptyl group, 1-methylheptyl group, n-octyl Group, fluoromethyl group, difluoromethyl group, trifluoromethyl group, chloromethyl group, dichloromethyl group, trichloromethyl group, bromomethyl group, dibromomethyl group, dichlorofluoromethyl group, 2,2,2-trifluoroethyl group, Pentafluoroethyl group, 2-chloroethyl group, 3,3,3-trifluoropropyl group, Pentafluoropropyl, heptafluoroisopropyl, 3-chloropropyl, 2-chloropropyl, 3-bromopropyl, 4,4,4-trifluorobutyl, 4,4,4,3,3-penta Fluorobutyl group, 4-chlorobutyl group, 4-bromobutyl group, 2-chlorobutyl group, 5,5,5-trifluoropentyl group, 5-chloropentyl group, 6,6,6-trifluorohexyl group, 6- Mention may be made of a C1-8 alkyl group in which 1 to 7 halogen atoms such as chlorohexyl group, 7-chloroheptyl group and 8-chlorooctyl group are substituted or unsubstituted.

  The C3-8 cycloalkyl-C1-6 alkyl group is a group composed of a C3-C8 cyclic alkyl group and a C1-C6 alkyl group, and examples thereof include a cyclopropylmethyl group, 2-Cyclopropylethyl group, 3-cyclopropylpropyl group, 4-cyclopropylbutyl group, 4-cyclopropylpentyl group, 6-cyclopropylhexyl group, cyclobutylmethyl group, 2-cyclobutylethyl group, 3-cyclo Butylpropyl group, 4-cyclobutylbutyl group, 4-cyclobutylpentyl group, 6-cyclobutylhexyl group, cyclopentylmethyl group, 2-cyclopentylethyl group, 3-cyclopentylpropyl group, 4-cyclopentylbutyl group, 4- A cyclopentylpentyl group, 6-cyclopentylhexyl group, cyclohexylmethyl group, -Cyclohexylethyl group, 3-cyclohexylpropyl group, 4-cyclohexylbutyl group, 4-cyclohexylpentyl group, 6-cyclohexylhexyl group, cycloheptylmethyl group, 2-cycloheptylethyl group, 3-cycloheptylpropyl group, 4- Cycloheptylbutyl group, 4-cycloheptylpentyl group, 6-cycloheptylhexyl group, cyclooctylmethyl group, 2-cyclooctylethyl group, 3-cyclooctylpropyl group, 4-cyclooctylbutyl group, 4-cyclooctylpentyl group Group, 6-cyclooctylhexyl group, etc. can be mentioned.

  Examples of the amino-C1-6 alkyl group which may have a C1-6 alkyl group include, for example, an amimethyl group, 2-aminoethyl group, 1-aminoethyl group, 3-aminopropyl group, 4-aminobutyl group, 5 -Aminopentyl group, 6-aminohexyl group, 2-methyl-3-aminopropyl group, 1,1-dimethyl-2-aminoethyl group, ethylaminomethyl group, 1- (propylamino) ethyl group, 2- ( Methylamino) ethyl group, 3- (isopropylamino) propyl group, 4- (n-butylamino) butyl group, 5- (n-pentylamino) pentyl group, 6- (n-hexylamino) hexyl group, dimethylamino 1 to 6 alkyl groups such as methyl group, (N-ethyl-N-propylamino) methyl group, 2- (N-methyl-N-hexylamino) ethyl group, etc. It may be mentioned certain amino -C1~6 alkyl group which may have pieces.

A phenyl C1-6 alkyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group, a halogen substituted or unsubstituted C1-6 alkoxy group, a halogen substituted or unsubstituted C1-6 alkylthio Group, phenyl C1-6 alkoxy group, hydroxy group, C1-6 alkylsulfinyl group, C1-6 alkylsulfonyl group, C1-6 alkylsulfonyloxy group, cyano group, C1-6 alkanoyl group, benzoyl group, C1 -C6 alkyl group optionally having 1 to 6 alkoxy group, amino group, nitro group, carbamoyl group, C1-6 alkanoylamino group, C1-6 alkoxycarbonyl group, C1-6 alkylaminocarbonyl group, C1-6 Alkoxycarbonylamino group, tri C 1-6 a As the pyrsiloxy group, the pyrrolyl group, the tetrahydropyranyloxy group and the imidazolyl group, a group selected from the group consisting of 1 to 5 groups may be substituted), for example, a benzyl group, 1-phenethyl group, 2-phenethyl group Group, 3-phenylpropyl group, 2-phenylpropyl group, 4-phenylbutyl group, 5-phenylpentyl group, 4-phenylpentyl group, 6-phenylhexyl group, 2-fluorobenzyl group, 3-fluorobenzyl group, 4-fluorobenzyl group, 2-chlorobenzyl group, 3-chlorobenzyl group, 4-chlorobenzyl group, 2-bromobenzyl group, 3-bromobenzyl group, 4-bromobenzyl group, 2-iodobenzyl group, 3- Iodobenzyl group, 4-iodobenzyl group, 2,3-difluorobenzyl group, 3,4-difluorobenzyl group 3,5-difluorobenzyl group, 2,3,4,5,6-pentafluorobenzyl group, 2,4-difluorobenzyl group, 2,6-difluorobenzyl group, 2,4,6-trifluorobenzyl group, 3,4,5-Trifluorobenzyl group, 2,3-dichlorobenzyl group, 3,4-dichlorobenzyl group, 3,5-dichlorobenzyl group, 2,4-dichlorobenzyl group, 2,6-dichlorobenzyl group 2,4,6-trichlorobenzyl, 3,4,5-trichlorobenzyl, perfluorobenzyl, 2-difluoromethylbenzyl, 3-difluoromethylbenzyl, 4-difluoromethylbenzyl, 4-chloro -3-difluoromethylbenzyl group, 3-chloro-4-difluoromethylbenzyl group, 3-bromo-4-difluoromethylbenzyl group 3,5-difluoro-4-difluoromethylbenzyl group, 2-methylbenzyl group, 3-methylbenzyl group, 4-methylbenzyl group, 2,3-dimethylbenzyl group, 2,4,6-trimethylbenzyl group, 3,5-ditrifluoromethylbenzyl group, 2-trifluoromethylbenzyl group, 3-trifluoromethylbenzyl group, 4-trifluoromethylbenzyl group, 4-fluoro-3-trifluoromethylbenzyl group, 3-fluoro- 4-trifluoromethylbenzyl group, 2-pentafluoroethyl benzyl group, 4-chloro-3-pentafluoroethyl benzyl group, 3-chloro-4-pentafluoroethyl benzyl group, 2-pentafluoroethyl benzyl group, 3- Pentafluoroethyl benzyl group, 4-pentafluoroethyl benzyl group, 2-methane Xybenzyl group, 3-methoxybenzyl group, 4-methoxybenzyl group, 2,3-dimethoxybenzyl group, 2,4,6-trimethoxybenzyl group, 3,5-ditrifluoromethoxybenzyl group, 2-trifluoromethoxybenzyl group Group, 3-trifluoromethoxybenzyl group, 4-trifluoromethoxybenzyl group, 4-fluoro-3-trifluoromethoxybenzyl group, 3-fluoro-4-trifluoromethoxybenzyl group, 2-pentafluoroethoxybenzyl group, 3-pentafluoroethoxybenzyl group, 4-pentafluoroethoxybenzyl group, 3-chloro-4-trifluoromethoxybenzyl group, 3-chloro-4-pentafluoroethoxybenzyl group, 2- (2-trifluoromethylphenyl) Ethyl group, 2- (3-trifluorome -Phenyl) ethyl group, 2- (4-trifluoromethylphenyl) ethyl group, 2-trifluoromethoxyphenyl) ethyl group, 3-trifluoromethoxyphenyl) ethyl group, 2- (4-trifluoromethoxyphenyl) ethyl group , 2- (2-pentafluoroethoxyphenyl) ethyl group, 2- (3-pentafluoroethoxyphenyl) ethyl group, 2- (4-pentafluoroethoxyphenyl) ethyl group, 3- (2-trifluoromethylphenyl) group Propyl group, 3- (3-trifluoromethylphenyl) propyl group, 3- (4-trifluoromethylphenyl) propyl group, 3- (2-trifluoromethoxyphenyl) propyl group, 3- (3-trifluoromethoxy Phenyl) propyl group, 3- (4-trifluoromethoxyphenyl) propyl Group, 3- (3-pentafluoroethoxyphenyl) propyl group, 3- (4-pentafluoroethoxyphenyl) propyl group, 4- (3-pentafluoroethoxyphenyl) butyl group, 5- (4-trifluoromethylphenyl) group ) Pentyl group, 4- (4-trifluoromethylphenyl) pentyl group, 4- (4-trifluoromethoxyphenyl) pentyl group, 6- (3-trifluoromethylphenyl) hexyl group, 6- (4-trifluoro) Methylphenyl) hexyl group, 6- (4-trifluoromethoxyphenyl) hexyl group, 2-methylthiobenzyl group, 3-methylthiobenzyl group, 4-methylthiobenzyl group, 2,3-dimethylthiobenzyl group, 2,4,4, 6-trimethylthiobenzyl group, 2- (2-methylthiophenyl) ethyl group, 2- (3- (3-methylthiophenyl) ethyl group Ethylthio, 2- (4-methylthiophenyl) ethyl, 3- (4-methylthiophenyl) propyl, 4- (4-methylthiophenyl) butyl, 5- (4-methylthiophenyl) pentyl , 6- (4-methylthiophenyl) hexyl group, 2-trifluoromethylthiobenzyl group, 3-trifluoromethylthiobenzyl group, 4-trifluoromethylthiobenzyl group, 2- (2-trifluoromethylthiophenyl) ethyl group, 2 -(3-trifluoromethylthiophenyl) ethyl group, 2- (4-trifluoromethylthiophenyl) ethyl group, 3- (4-trifluoromethylthiophenyl) propyl group, 4- (4-trifluoromethylthiophenyl) butyl group , 5- (4-trifluoromethylthiophenyl) pentyl group, -(4-trifluoromethylthiophenyl) hexyl group, 2-benzyloxybenzyl group, 3-benzyloxybenzyl group, 4-benzyloxybenzyl group, 2- (2-benzyloxyphenyl) ethyl group, 2- (3- Benzyloxyphenyl) ethyl group, 2- (4-benzyloxyphenyl) ethyl group, 3- (4-benzyloxyphenyl) propyl group, 4- (4-benzyloxyphenyl) butyl group, 5- (4-benzyloxy) Phenyl) pentyl group, 6- (4-benzyloxyphenyl) hexyl group, 2- (2-phenylethoxy) benzyl group, 3- (2-phenylethoxy) benzyl group, 4- (2-phenylethoxy) benzyl group, 2- [2- (2-phenylethoxyphenyl)] ethyl group, 2- [3- (2-phenylethoxyphen) Group] ethyl group, 2- [4- (2-phenylethoxyphenyl)] ethyl group, 3- [4- (2-phenylethoxyphenyl)] propyl group, 4- [4- (2-phenylethoxyphenyl) group Butyl group, 5- [4- (2-phenylethoxyphenyl)] pentyl group, 6- [4- (2-phenylethoxyphenyl)] hexyl group, 2- (3-phenylpropoxy) benzyl group, 3- (3- 3-phenylpropoxy) benzyl group, 4- (3-phenylpropoxy) benzyl group, 2- (4-phenylbutoxy) benzyl group, 3- (4-phenylbutoxy) benzyl group, 4- (4-phenylbutoxy) benzyl Group, 2-methoxy carbonyl benzyl group, 3- methoxy carbonyl benzyl group, 4- methoxy carbonyl benzyl group, 2- (2- methoxy carbo) Lephenyl) ethyl group, 2- (3-methoxycarbonylphenyl) ethyl group, 2- (4-methoxycarbonylphenyl) ethyl group, 3- (4-methoxycarbonylphenyl) propyl group, 4- (4-methoxycarbonylphenyl) Butyl, 5- (4-methoxycarbonylphenyl) pentyl, 6- (4-methoxycarbonylphenyl) hexyl, 2-hydroxybenzyl, 3-hydroxybenzyl, 4-hydroxybenzyl, 2,3-dihydroxy Benzyl group, 2,4,6-trihydroxybenzyl group, 2- (2-hydroxyphenyl) ethyl group, 2- (3-hydroxyphenyl) ethyl group, 2- (4-hydroxyphenyl) ethyl group, 3- ( 4-hydroxyphenyl) propyl group, 4- (4-hydroxyphenyl) butyl group 5- (4-hydroxyphenyl) pentyl group, 6- (4-hydroxyphenyl) hexyl group, 2-methylsulfinylbenzyl group, 3-methylsulfinylbenzyl group, 4-methylsulfinylbenzyl group, 2,3-dimethylsulfinylbenzyl group Group, 2,4,6-trimethylsulfinylbenzyl group, 2- (2-methylsulfinylphenyl) ethyl group, 2- (3-methylsulfinylphenyl) ethyl group, 2- (4-methylsulfinylphenyl) ethyl group, 3 -(4-methylsulfinylphenyl) propyl group, 4- (4-methylsulfinylphenyl) butyl group, 5- (4-methylsulfinylphenyl) pentyl group, 6- (4-methylsulfinylphenyl) hexyl group, 2-methane Sulfonyl benzyl group, 3-methanesulfonyl Benzyl, 4-methanesulfonylbenzyl, 2,3-dimethanesulfonylbenzyl, 2,4,6-trimethanesulfonylbenzyl, 2- (2-methanesulfonylphenyl) ethyl, 2- (3-methane Sulfonylphenyl) ethyl group, 2- (4-methanesulfonylphenyl) ethyl group, 3- (4-methanesulfonylphenyl) propyl group, 4- (4-methanesulfonylphenyl) butyl group, 5- (4-methanesulfonylphenyl) ) Pentyl group, 6- (4-methanesulfonylphenyl) hexyl group, 2-methanesulfonyloxybenzyl group, 3-methanesulfonyloxybenzyl group, 4-methanesulfonyloxybenzyl group, 2,3-dimethanesulfonyloxybenzyl group , 2,4,6-trimethanesulfonyloxy benzyl group, 2- 2-methanesulfonyloxyphenyl) ethyl group, 2- (3-methanesulfonyloxyphenyl) ethyl group, 2- (4-methanesulfonyloxyphenyl) ethyl group, 3- (4-methanesulfonyloxyphenyl) propyl group, 4 -(4-methanesulfonyloxyphenyl) butyl group, 5- (4-methanesulfonyloxyphenyl) pentyl group, 6- (4-methanesulfonyloxyphenyl) hexyl group, 2-cyanobenzyl group, 3-cyanobenzyl group, 4-cyanobenzyl group, 2,3-dicyanobenzyl group, 2,4,6-tricyanobenzyl group, 2- (2-cyanophenyl) ethyl group, 2- (3-cyanophenyl) ethyl group, 2- (2- 4-cyanophenyl) ethyl group, 3- (4-cyanophenyl) propyl group, 4- (4-cyanophenyl) Ethyl, 5- (4-cyanophenyl) pentyl, 6- (4-cyanophenyl) hexyl, 2-acetylbenzyl, 3-acetylbenzyl, 4-acetylbenzyl, 2- (2-acetylphenyl) ) Ethyl group, 2- (3-acetylphenyl) ethyl group, 2- (4-acetylphenyl) ethyl group, 3- (4-acetylphenyl) propyl group, 4- (4-acetylphenyl) butyl group, 5- (4-acetylphenyl) pentyl group, 6- (4-acetylphenyl) hexyl group, 2-benzoylbenzyl group, 3-benzoylbenzyl group, 4-benzoylbenzyl group, 2- (2-benzoylphenyl) ethyl group, 2 -(3-benzoylphenyl) ethyl group, 2- (4-benzoylphenyl) ethyl group, 3- (4-benzoylphenyl) propyl group 4- (4-benzoylphenyl) butyl group, 5- (4-benzoylphenyl) pentyl group, 6- (4-benzoylphenyl) hexyl group, 2-α, α-dimethoxybenzylbenzyl group, 3-α, α -Dimethoxybenzylbenzyl group, 4-α, α-dimethoxybenzyl


Benzyl group, 2- (2-α, α-dimethoxybenzylphenyl) ethyl group, 2- (3- (α, α-dimethoxybenzyl) phenyl) ethyl group, 2- (4- (α, α-dimethoxybenzyl) group Phenyl) ethyl group, 3- (4- (α, α-dimethoxybenzyl) phenyl) propyl group, 4- (4- (α, α-dimethoxybenzyl) phenyl) butyl group, 5- (4- (α, α) -Dimethoxybenzyl) phenyl) pentyl, 6- (4- (α, α-dimethoxybenzyl) phenyl) hexyl, 2-aminobenzyl, 3-aminobenzyl, 4-aminobenzyl, 2,3-diamino Benzyl group, 2,4,6-triaminobenzyl group, 2- (2-aminophenyl) ethyl group, 2- (3-aminophenyl) ethyl group, 2- (4-aminophenyl) ethyl group, 3- ( 4-aminophenyl) propyl group, 4- (4-aminophenyl) butyl group, 5- (4-aminophenyl) pentyl group, 6- (4-aminophenyl) hexyl group, 2-nitrobenzyl group, 3-nitro Benzyl group, 4-nitrobenzyl group, 2,4-dinitrobenzyl group, 2,4,6-trinitrobenzyl group, 2- (2-nitrophenyl) ethyl group, 2- (3-nitrophenyl) ethyl group, 2- (4-nitrophenyl) ethyl group, 3- (4-nitrophenyl) propyl group, 4- (4-nitrophenyl) butyl group, 5- (4-nitrophenyl) pentyl group, 6- (4-nitro) Phenyl) hexyl group, 2-carbamoyl benzyl group, 3-carbamoyl benzyl group, 4-carbamoyl benzyl group, 2- (2-carbamoylphenyl) ethyl group, 2- (3- Ruvamoylphenyl) ethyl group, 2- (4-carbamoylphenyl) ethyl group, 3- (4-carbamoylphenyl) propyl group, 4- (4-carbamoylphenyl) butyl group, 5- (4-carbamoylphenyl) pentyl group 6- (4-carbamoylphenyl) hexyl group, 2-acetylaminobenzyl group, 3-acetylaminobenzyl group, 4-acetylaminobenzyl group, 2- (2-acetylaminophenyl) ethyl group, 2- (3- Acetylaminophenyl) ethyl group, 2- (4-acetylaminophenyl) ethyl group, 3- (4-acetylaminophenyl) propyl group, 4- (4-acetylaminophenyl) butyl group, 5- (4-acetylamino) Phenyl) pentyl group, 6- (4-acetylaminophenyl) hexyl group, 2-ethoxy carbon Bonylbenzyl, 3-ethoxycarbonylbenzyl, 4-ethoxycarbonylbenzyl, 2- (2-ethoxycarbonylphenyl) ethyl, 2- (3-ethoxycarbonylphenyl) ethyl, 2- (4-ethoxycarbonylphenyl) Ethyl group, 3- (4-ethoxycarbonylphenyl) propyl group, 4- (4-ethoxycarbonylphenyl) butyl group, 5- (4-ethoxycarbonylphenyl) pentyl group, 6- (4-ethoxycarbonylphenyl) hexyl group , 2-methylaminocarbonylbenzyl group, 3-methylaminocarbonylbenzyl group, 4-methylaminocarbonylbenzyl group, 2-dimethylaminocarbonylbenzyl group, 3-dimethylaminocarbonylbenzyl group, 2-ethylaminocarbonylbenzyl group, 3 -D 2-methylaminocarbonylbenzyl group, 4-ethylaminocarbonylbenzyl group, 4-dimethylaminocarbonylbenzyl group, 2-diethylaminocarbonylbenzyl group, 3-diethylaminocarbonylbenzyl group, 4-diethylaminocarbonylbenzyl group, 2- (di-n-) Propylaminocarbonyl) benzyl group, 3- (di-n-propylaminocarbonyl) benzyl group, 4- (di-n-propylaminocarbonyl) benzyl group, 2-methoxycarbonylaminobenzyl group, 3-methoxycarbonylaminobenzyl group , 4-Methoxycarbonylaminobenzyl, 2-ethoxycarbonylaminobenzyl, 3-ethoxycarbonylaminobenzyl, 4-ethoxycarbonylaminobenzyl, 2- (tert-butoxycarbonylamino) Benzyl, 3- (tert-butoxycarbonylamino) benzyl, 4- (tert-butoxycarbonylamino) benzyl, 4-trimethylsiloxybenzyl, 4-triethylsiloxybenzyl, 2-pyrrolylbenzyl, 3- Pyrrolyl benzyl group, 4-pyrrolyl benzyl group, 2- (1-imidazolyl) benzyl group, 3- (1-imidazolyl) benzyl group, 4- (1-imidazolyl) benzyl group, 2- (2-tetrahydropyranyl) Examples include oxy) benzyl group, 3- (2-tetrahydropyranyloxy) benzyl group, 4- (2-tetrahydropyranyloxy) benzyl group and the like.

  Examples of the benzhydryl group (wherein at least one member selected from the group consisting of a halogen atom, a trifluoromethyl group and a trifluoromethoxy group may be substituted on the benzene ring) include, for example, a benzhydryl group, 4 4,4'-Dichlorobenzhydryl, 4,4'-Difluorobenzhydryl, 4,4'-Ditrifluoromethylbenzhydryl, 4,4'-Ditrifluoromethoxybenzhydryl, etc. Can.

  Examples of the phenyl C2-6 alkynyl group (in the phenyl ring, at least one of halogen substituted or unsubstituted C1-6 alkyl group may be substituted) include, for example, 2-phenylethynyl group, 3-phenyl -2-propynyl group, 4-phenyl-3-butynyl group, 4-phenyl-2-butynyl group, 5-phenyl-4-pentynyl group, 6-phenyl-5-hexynyl group, 2-methylphenyl-2-propynyl group Group, 3-methylphenyl-3-butynyl group, 4-methylphenyl-2-butynyl group, 2,4-ditylphenyl-4-pentynyl group, 2,4,6-trimethylphenyl-5-hexynyl group, 3, 5-ditrifluoromethylphenyl-2-propynyl group, 2-trifluoromethylphenyl-3-butynyl group, 3-trifluoromethylphenyl Phenyl C2-6 alkynyl groups such as 2-butynyl group, 4-trifluoromethylphenyl-2-propynyl group (1 to 3 halogen-substituted or unsubstituted C1-6 alkyl groups as substituents on the phenyl ring And may be substituted).

  Examples of the phenyl C2-6 alkynyl group (on the phenyl ring, at least one halogen-substituted or unsubstituted C1-6 alkyl group may be substituted) include, for example, 2-phenylethynyl group, 3-phenyl -2-propynyl group, 4-phenyl-3-butynyl group, 4-phenyl-2-butynyl group, 5-phenyl-4-pentynyl group, 6-phenyl-5-hexynyl group, 2-methylphenyl-2-propynyl group Group, 3-methylphenyl-3-butynyl group, 4-methylphenyl-2-butynyl group, 2,4-ditylphenyl-4-pentynyl group, 2,4,6-trimethylphenyl-5-hexynyl group, 3, 5-ditrifluoromethylphenyl-2-propynyl group, 2-trifluoromethylphenyl-3-butynyl group, 3-trifluoromethylphenyl Phenyl C2-6 alkynyl groups such as 2-butynyl group, 4-trifluoromethylphenyl-2-propynyl group (1 to 3 halogen-substituted or unsubstituted C1-6 alkyl groups as substituents on the phenyl ring And may be substituted).

  As the pyridyl C1-6 alkyl group, for example, 2-pyridylmethyl group, 2- (3-pyridyl) ethyl group, 1- (4-pyridyl) ethyl group, 3- (2-pyridyl) propyl group, 4- (4- 3-pyridyl) butyl, 5- (4-pyridyl) pentyl, 6- (2-pyridyl) hexyl, 2-methyl-3- (3-pyridyl) propyl, 1,1-dimethyl-2- ( 2-pyridyl) ethyl etc. can be mentioned.

  Examples of the piperidino C1-6 alkyl group (on the piperidine ring, a phenoxy group which may have at least one halogen-substituted or unsubstituted alkyl group as a substituent on the phenyl ring may be substituted) include, for example, , Piperidin-1-ylmethyl group, 2- (piperidin-2-yl) ethyl group, 3- (piperidin-3-yl) propyl group, 4- (piperidin-4-yl) butyl group, 5- (piperidine-1) -Yl) pentyl, 6- (piperidin-1-yl) hexyl, 4- (4-trifluoromethylphenoxy) piperidin-1-ylmethyl, 4-phenoxypiperidin-1-ylmethyl, 4- (4- Methylphenoxy) piperidin-1-ylmethyl group, 4- (2,4-dimethylphenoxy) piperidin-1-ylmethyl group, 4- (4- (2,4-dimethylphenoxy) piperidin-1-ylmethyl group , 4,6-trimethylphenoxy) piperidin-1-ylmethyl group, 2- [4- (4-trifluoromethylphenoxy) piperidin-1-yl] ethyl group, 3- [4- (4-trifluoromethylphenoxy) group Piperidin-1-yl] propyl group, 4- [4- (4-trifluoromethylphenoxy) piperidin-1-yl] butyl group, 5- [4- (4-trifluoromethylphenoxy) piperidin-1-yl] Piperidino C1-6 alkyl groups such as pentyl group, 6- [4- (4-trifluoromethylphenoxy) piperidin-1-yl] hexyl group (on the piperidine ring, halogen-substituted or unsubstituted as a substituent on the phenyl ring And phenoxy groups which may have 1 to 3 substituted alkyl groups may be substituted).

  Amino C1-6 alkyl group (selected from the group consisting of a C1-6 alkyl group on the amino group and a phenyl group which may have a halogen substituted or unsubstituted C1-6 alkoxy group as a substituent on the phenyl ring As at least one kind of substituted group) may be, for example, aminomethyl group, 2-aminoethyl group, 2-aminopropyl group, 3-aminopropyl group, 3-aminobutyl group, 4-amino Butyl group, 5-aminopentyl group, 6-aminohexyl group, 2-methylaminoethyl group, 2-methylaminopropyl group, 3-methylaminopropyl group, 3-methylaminobutyl group, 4-methylaminobutyl group, 5-methylaminopentyl group, 6-methylaminohexyl group, 2- (ethylamino) ethyl group, 3- (ethylamino) propyl group, 4- Ethylamino) butyl, 5- (ethylamino) pentyl, 6- (ethylamino) hexyl, 2- (n-propylamino) ethyl, 3- (n-propylamino) propyl, 4- (n -Propylamino) butyl group, 5- (n-propylamino) pentyl group, 6- (n-propylamino) hexyl group, 2- (n-butylamino) ethyl group, 3- (n-butylamino) propyl group , 2- (n-pentylamino) ethyl group, 3- (n-pentylamino) propyl group, 2- (n-hexylamino) ethyl group, 3- (n-hexylamino) propyl group, 2-dimethylaminoethyl group Group, 2-dimethylaminopropyl group, 3-dimethylaminopropyl group, 3-dimethylaminobutyl group, 4-dimethylaminobutyl group, 5-dimethylaminopentyl group 6-dimethylaminohexyl group, 2- (diethylamino) ethyl group, 3- (diethylamino) propyl group, 4- (diethylamino) butyl group, 5- (diethylamino) pentyl group, 6- (diethylamino) hexyl group, 2- (2- (diethylamino) hexyl group) Di-n-propylamino) ethyl group, 3- (di-n-propylamino) propyl group, 4- (di-n-propylamino) butyl group, 5- (di-n-propylamino) pentyl group, 6 -(Di-n-propylamino) hexyl group, 2- (phenylamino) ethyl group, 3- (phenylamino) propyl group, 4- (phenylamino) butyl group, 5- (phenylamino) pentyl group, 6- (Phenylamino) hexyl group, 2- (N-methyl-N-phenylamino) ethyl group, 3- (N-methyl-N-phenylamino) propyl group, 4- (N-methyl-N-phenylamino) butyl group, 5- (N-methyl-N-phenylamino) pentyl group, 6- (N-methyl-N-phenylamino) hexyl group, (4-methoxyphenyl) ) Aminomethyl group, (3,4-dimethoxyphenyl) aminomethyl group, (2,4,6-trimethoxyphenyl) aminomethyl group, 2- (4-trifluoromethoxyphenylamino) ethyl group, 3- (4 (4) -Trifluoromethoxyphenylamino) propyl group, 4- (4-trifluoromethoxyphenylamino) butyl group, 5- (4-trifluoromethoxyphenylamino) pentyl group, 6- (4-trifluoromethoxyphenylamino) hexyl Group, 2- (N-methyl-N-4-trifluoromethoxyphenylamino) ethyl group, 3- (N-methyl-N-) -Trifluoromethoxyphenylamino) propyl group, 4- (N-methyl-N-4-trifluoromethoxyphenylamino) butyl group, 5- (N-methyl-N-4-trifluoromethoxyphenylamino) pentyl group, As a substituent such as 6- (N-methyl-N-4-trifluoromethoxyphenylamino) hexyl group, a C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group as a substituent on a phenyl ring The amino C1-6 alkyl group which may have 1-2 groups selected from the group which consists of a phenyl group which may have -3 can be mentioned.

  1,2,3,6-tetrahydropyridyl C1-6 alkyl group (1,2,3,6-tetrahydropyridine ring, at least one phenyl group [phenyl ring or halogen-substituted or unsubstituted As the C1-6 alkoxy group, at least one of them may be substituted] may be substituted, for example, (1,2,3,6-tetrahydropyridin-1-yl) methyl group, 1- (1,2,3,6-tetrahydropyridin-2-yl) ethyl group, 2- (1,2,3,6-tetrahydropyridin-3-yl) ethyl group, 3- (1,2,3,6 -Tetrahydropyridin-4-yl) propyl group, 4- (1,2,3,6-tetrahydropyridin-1-yl) butyl group, 5- (1,2,3,6-tetrahydropyridin-2-yl) Pentyl group, 6- (1, , 3,6-tetrahydropyridin-3-yl) hexyl group, 2-methyl-3- (1,2,3,6-tetrahydropyridin-1-yl) propyl group, 1,1-dimethyl-2- (1 2,2,3,6-Tetrahydropyridin-4-yl) ethyl group, 4-phenyl-1,2,3,6-tetrahydropyridin-1-ylmethyl group, 3,4,5-triphenyl-1,2,5 3,6-Tetrahydropyridin-1-ylmethyl group, 3,4-diphenyl-1,2,3,6-tetrahydropyridin-1-ylmethyl group, 4- (2-methoxyphenyl) -1,2,3,6 -Tetrahydropyridin-1-ylmethyl group, 4- (3-methoxyphenyl) -1,2,3,6-tetrahydropyridin-1-ylmethyl group, 4- (4-methoxyphenyl) -1,2,3,6 -Tet Hydropyridin-1-ylmethyl group, 4- (2,4-dimethoxyphenyl) -1,2,3,6-tetrahydropyridin-1-ylmethyl group, 3- (2,4,6-trimethoxyphenyl) -1 2,2,3,6-Tetrahydropyridin-1-ylmethyl group, 4- (2-trifluoromethoxyphenyl) -1,2,3,6-tetrahydropyridin-1-ylmethyl group, 4- (3-trifluoromethoxy Phenyl) -1,2,3,6-tetrahydropyridin-1-ylmethyl group, 4- (3,5-ditrifluoromethoxyphenyl) -1,2,3,6-tetrahydropyridin-1-ylmethyl group, 4- (4-trifluoromethoxyphenyl) -1,2,3,6-tetrahydropyridin-1-ylmethyl group, 2- (4-phenyl-1,2,3,6-tetraphenyl) Dolopyridin-1-yl) ethyl group, 2- [4- (4-methoxyphenyl) -1,2,3,6-tetrahydropyridin-1-yl] ethyl group, 2- [4- (4-trifluoromethoxy) Phenyl) -1,2,3,6-tetrahydropyridin-1-yl] ethyl group, 3- (4-phenyl-1,2,3,6-tetrahydropyridin-1-yl) propyl group, 3- [4 -(4-Methoxyphenyl) -1,2,3,6-tetrahydropyridin-1-yl] propyl group, 3- [4- (4-trifluoromethoxyphenyl) -1,2,3,6-tetrahydropyridine -1-yl] propyl group, 4- (4-phenyl-1,2,3,6-tetrahydropyridin-1-yl) butyl group, 4- [4- (4-methoxyphenyl) -1,2,3 , 6-Tetrahydropyridine -1-yl] butyl group, 4- [4- (4-trifluoromethoxyphenyl) -1,2,3,6-tetrahydropyridin-1-yl] butyl group, 5- (4-phenyl-1,2 , 3,6-tetrahydropyridin-1-yl) pentyl, 5- [4- (4-methoxyphenyl) -1,2,3,6-tetrahydropyridin-1-yl] pentyl, 5- [4- (4-Trifluoromethoxyphenyl) -1,2,3,6-tetrahydropyridin-1-yl] pentyl group, 6- (4-phenyl-1,2,3,6-tetrahydropyridin-1-yl) hexyl Group, 6- [4- (4-methoxyphenyl) -1,2,3,6-tetrahydropyridin-1-yl] hexyl group, 6- [4- (4-trifluoromethoxyphenyl) -1,2,4, 3,6-tetrahydro 1,2,3,6-Tetrahydropyridyl C1-6 alkyl groups such as a lysine-1-yl] hexyl group (on the 1,2,3,6-tetrahydropyridine ring, halogen substitution on the phenyl ring as a substituent) Alternatively, 1 to 3 phenyl groups which may have 1 to 3 unsubstituted C1-6 alkoxy groups may be substituted. Can be mentioned.

  As the fluorenyl C1-6 alkyl group, for example, 1-fluorenyl methyl group, 2-fluorenyl methyl group, 3-fluorenyl methyl group, 4-fluorenyl methyl group, 9-fluorenyl methyl group , 2- (1-fluorenyl) ethyl group, 2- (2-fluorenyl) ethyl group, 2- (3-fluorenyl) ethyl group, 2- (4-fluorenyl) ethyl group, 2- (9-fluorenyl) ethyl group , 3- (1-fluorenyl) propyl group, 3- (2-fluorenyl) propyl group, 3- (3-fluorenyl) propyl group, 3- (4-fluorenyl) propyl group, 3- (9-fluorenyl) propyl group , 4- (1-fluorenyl) butyl group, 4- (2-fluorenyl) butyl group, 5- (1-fluorenyl) pentyl group, 5- (2-fluorenyl) pentyl group 6- (1-fluorenyl) hexyl group, 6- (2-fluorenyl) and a hexyl group.

  Examples of the furyl C1-6 alkyl group (a halogen-substituted or unsubstituted phenyl group may be substituted on the furan ring) include, for example, 2-furylmethyl group, 3-furylmethyl group, 2- (2) -Furyl) ethyl group, 1- (3-furyl) ethyl group, 3- (2-furyl) propyl group, 3- (3-furyl) propyl group, 4- (2-furyl) butyl group, 4- (3) -Furyl) butyl group, 5- (2-furyl) pentyl group, 5- (3-furyl) pentyl group, 6- (2-furyl) hexyl group, 6- (3-furyl) hexyl group, 4-phenyl- 2-furylmethyl group, 4- (2-fluorophenyl) -2-furylmethyl group, 4- (3-fluorophenyl) -2-furylmethyl group, 4- (4-fluorophenyl) -2-furylmethyl group , 4- (2,3,4,5,6-pen Fluorophenyl) -2-furylmethyl group, 4- (2-chlorophenyl) -2-furylmethyl group, 4- (3-chlorophenyl) -2-furylmethyl group, 4- (4-chlorophenyl) -2-furylmethyl Group, 4- (2-bromophenyl) -2-furylmethyl group, 4- (3-bromophenyl) -2-furylmethyl group, 4- (4-bromophenyl) -2-furylmethyl group, 4-phenyl -3-furyl methyl group, 4- (2,3-dichlorophenyl) -3-furyl methyl group, 4- (4-chlorophenyl) -3-furyl methyl group, 4- (2-bromophenyl) -3-furyl methyl group Group, 4- (3-bromophenyl) -3-furylmethyl group, 4- (4-bromophenyl) -3-furylmethyl group, 4-phenyl-3-furylethyl group, 2- [4- (3-) Chloro Phenyl) -3-furyl] ethyl group, 2- [4- (4-chlorophenyl) -3-furyl] ethyl group, 2- [4- (2-bromophenyl) -3-furyl] ethyl group, 2- [4 4- (3-bromophenyl) -3-furyl] ethyl group, 2- [4- (2,4-dibromophenyl) -3-furyl] ethyl group, 2- (4-phenyl-2-furyl) ethyl group , 2- [4- (3-chlorophenyl) -2-furyl] ethyl group, 2- [4- (4-chlorophenyl) -2-furyl] ethyl group, 2- [4- (4-bromophenyl) -2 -Furyl] ethyl group, 3- (4-phenyl-3-furyl) propyl group, 3- [4- (3-chlorophenyl) -3-furyl] propyl group, 3- [4- (2,4,6-) Trichlorophenyl) -3-furyl] propyl group, 3- [4- (4-bromo) Phenyl) -3-furyl] propyl group, 3- (4-phenyl-2-furyl) propyl group, 3- [4- (3-chlorophenyl) -2-furyl] propyl group, 3- [4- (4- (4- (4-chlorophenyl) propyl) group] Chlorophenyl) -2-furyl] propyl group, 3- [4- (4-bromophenyl) -2-furyl] propyl group, 4- (4-phenyl-3-furyl) butyl group, 4- [4- (3) -Chlorophenyl) -3-furyl] butyl group, 4- [4- (4-chlorophenyl) -3-furyl] butyl group, 4- [4- (4-bromophenyl) -3-furyl] butyl group, 4- (4-phenyl-2-furyl) butyl group, 4- [4- (3-chlorophenyl) -2-furyl] butyl group, 4- [4- (4-chlorophenyl) -2-furyl] butyl group, 4- [4- (4-bromophenyl) -2-furyl] Group, 5- (4-phenyl-3-furyl) pentyl group, 5- [4- (3-chlorophenyl) -3-furyl] pentyl group, 5- [4- (4-chlorophenyl) -3-furyl] A pentyl group, 5- [4- (4-bromophenyl) -3-furyl] pentyl group, 5- (4-phenyl-2-furyl) pentyl group, 5- [4- (3-chlorophenyl) -2-furyl Pentyl group, 5- [4- (4-chlorophenyl) -2-furyl] pentyl group, 5- [4- (4-bromophenyl) -2-furyl] pentyl group, 6- (4-phenyl-3-phenyl) group Furyl) hexyl group, 6- [4- (3-chlorophenyl) -3-furyl] hexyl group, 6- [4- (4-chlorophenyl) -3-furyl] hexyl group, 6- [4- (4-bromo) Phenyl) -3-furyl] hexyl group, 6- 4-phenyl-2-furyl) hexyl group, 6- [4- (3-chlorophenyl) -2-furyl] hexyl group, 6- [4- (4-chlorophenyl) -2-furyl] hexyl group, 6- [6 Furyl C1-6 alkyl groups such as 4- (4-bromophenyl) -2-furyl] hexyl group (1 to 5 halogen atoms may be substituted or unsubstituted on the furan ring; Good) can be mentioned.

  As a thienyl substituted C1-6 alkyl group, for example, 2-thienylmethyl group, 3-thienylmethyl group, 2- (2-thienyl) ethyl group, 1- (3-thienyl) ethyl group, 4- (2-thienyl group ) Butyl group, 4- (3-thienyl) butyl group, 5- (2-thienyl) pentyl group, 5- (3-thienyl) pentyl group, 6- (2-thienyl) hexyl group, 6- (3-thienyl group Hexyl group etc. can be mentioned.

  Examples of the oxazolyl C1-6 alkyl group (a halogen atom or a halogen-substituted or unsubstituted phenyl group may be substituted on the oxazole ring) include, for example, 2-oxazolylmethyl group, 4-oxazolyl Methyl group, 5-oxazolylmethyl group, 2- (2-oxazolyl) ethyl group, 1- (4-oxazolyl) ethyl group, 3- (2-oxazolyl) propyl group, 4- (2-oxazolyl) butyl group , 5- (2-oxazolyl) pentyl group, 6- (2-oxazolyl) hexyl group, 2- (4-oxazolyl) ethyl group, 3- (4-oxazolyl) propyl group, 4- (4-oxazolyl) butyl group , 5- (4-oxazolyl) pentyl, 6- (4-oxazolyl) hexyl, 2-chloro-4-oxazolylmethyl, 2,5-dichloro 4-oxazolylmethyl group, 2,5-diphenyl-4-oxazolylmethyl group, 2- (2-chloro-4-oxazolyl) ethyl group, 3- (2-chloro-4-oxazolyl) propyl group, 4- (2-iodo-4-oxazolyl) butyl group, 5- (2-bromo-4-oxazolyl) pentyl group, 6- (2-fluoro-4-oxazolyl) hexyl group, 2- (4-chlorophenyl)- 4-oxazolylmethyl group, 2- (2,3,4,5,6-pentafluorophenyl) -4-oxazolylmethyl group, 2- [2- (4-chlorophenyl) -4-oxazolyl] ethyl Group, 3- [2- (4-chlorophenyl) -4-oxazolyl] propyl group, 4- [2- (2,4,6-trichlorophenyl) -4-oxazolyl] butyl group, 5- [2- (4) -Chloro Oxazolyl such as Phenyl) -4-oxazolyl] pentyl, 6- [2- (4-chlorophenyl) -4-oxazolyl] hexyl, [2-chloro-4- (3-chlorophenyl) -5-oxazolyl] methyl and the like A C1-6 alkyl group (A halogen atom on the oxazole ring or a phenyl group which may be substituted by 1 to 5 halogen atoms on the phenyl ring may be optionally substituted).

  Examples of the oxadiazolyl C1-6 alkyl group (a halogen-substituted or unsubstituted phenyl group may be substituted on the oxadiazole ring) include, for example, 5-oxadiazolylmethyl group, 2- (5-oxadiazolyl) ) Ethyl group, 1- (2-oxadiazolyl) ethyl group, 3- (5-oxadiazolyl) propyl group, 4- (2-oxadiazolyl) butyl group, 5- (5-oxadiazolyl) pentyl group, 6- (2-oxadiazolyl) group ) Hexyl group, 2-methyl-3- (2-oxadiazolyl) propyl group, 1,1-dimethyl-2- (5-oxadiazolyl) ethyl group, 2-phenyl-5-oxadiazolylmethyl group, 2- (2 -Fluorophenyl) -5-oxadiazolylmethyl group, 2- (3-fluorophenyl) -5-oxadiazolyl Ethyl, 2- (2,3,4,5,6-pentafluorophenyl) -5-oxadiazolylmethyl, 2- (2,4-dichlorophenyl) -5-oxadiazolylmethyl, 2- ( 3-chlorophenyl) -5-oxadiazolylmethyl group, 2- (4-chlorophenyl) -5-oxadiazolylmethyl group, 2- (2-bromophenyl) -5-oxadiazolylmethyl group, 2- (2 , 4,6-tribromophenyl) -5-oxadiazolylmethyl group, 2- (4-bromophenyl) -5-oxadiazolylmethyl group, 2- (5-oxadiazolyl) ethyl group, 3- (5- Oxadiazolyl) propyl group, 4- (5-oxadiazolyl) butyl group, 5- (5-oxadiazolyl) pentyl group, 6- (5-oxadiazolyl) hexyl group, 2- (2-fluoro) Nyl-5-oxadiazolyl) ethyl group, 3- (2-phenyl-5-oxadiazolyl) propyl group, 4- (2-phenyl-5-oxadiazolyl) butyl group, 5- (2-phenyl-5-oxadiazolyl) pentyl group , 6- (2-phenyl-5-oxadiazolyl) hexyl group, 2- [2- (4-chlorophenyl) -5-oxadiazolyl] ethyl group, 3- [2- (4-chlorophenyl) -5-oxadiazolyl] propyl group 4- [2- (4-chlorophenyl) -5-oxadiazolyl] butyl group, 5- [2- (4-chlorophenyl) -5-oxadiazolyl] pentyl group, 6- [2- (4-chlorophenyl) -5-yl group Oxadiazolyl C1-6 alkyl groups such as oxadiazolyl] hexyl group (one halogen atom is present on the oxadiazole ring And 5-substituted or unsubstituted phenyl groups may be substituted).

  As a pyrazolyl C1-6 alkyl group (a halogen-substituted or unsubstituted phenyl group may be substituted on the pyrazole ring), for example, 3-pyrazolylmethyl group, 2- (4-pyrazolyl) ethyl group, 1- (5-pyrazolyl) ethyl group, 3- (3-pyrazolyl) propyl group, 4- (4-pyrazolyl) butyl group, 5- (1-pyrazolyl) pentyl group, 6- (5-pyrazolyl) hexyl group, 2-methyl-3- (1-pyrazolyl) propyl group, 1,1-dimethyl-2- (3-pyrazolyl) ethyl group, 1- (1-phenyl-3-pyrazolylmethyl group, 1- (2-fluorophenyl) group ) 4-Pyrazolylmethyl group, 1- (3-fluorophenyl) -3-pyrazolylmethyl group, 3-phenyl-1-pyrazolylmethyl group, 3,4,5-triphenyl-1-yl Razolyl methyl group, 3,4-diphenyl-1-pyrazolyl methyl group, 1- (4-fluorophenyl) -3-pyrazolyl methyl group, 1- (2,3,4,5,6-pentafluorophenyl) -3- Pyrazolylmethyl group, 1- (2-chlorophenyl) -5-pyrazolylmethyl group, 1- (3-chlorophenyl) -3-pyrazolylmethyl group, 1- (4-chlorophenyl) -3-pyrazolylmethyl group, 1- (2) -Bromophenyl) -3-pyrazolylmethyl group, 1- (3-bromophenyl) -3-pyrazolylmethyl group, 1- (4-bromophenyl) -3-pyrazolylmethyl group, 2- (3-pyrazolyl) ethyl group 3- (3-pyrazolyl) propyl group, 4- (3-pyrazolyl) butyl group, 5- (3-pyrazolyl) pentyl group, 6- (3-pyrazolyl) hexy Group, 2- [1- (4-chlorophenyl) -3-pyrazolyl] ethyl group, 3- [1- (2,4-dichlorophenyl) -3-pyrazolyl] propyl group, 4- [1- (4-chlorophenyl) group -3-pyrazolyl] butyl group, 5- [1- (4-chlorophenyl) -3-pyrazolyl] pentyl group, 6- [1- (2,4,6-trichlorophenyl) -3-pyrazolyl] hexyl group, etc. There may be mentioned pyrazolyl C1-6 alkyl groups (1 to 5 halogen atoms may be substituted on the pyrazole ring or 1 to 3 substituted phenyl groups may be substituted).

  As a benzothienyl C1 to 6 alkyl group (on the benzothiophene ring, at least one of a group selected from the group consisting of a halogen atom and a halogen substituted or unsubstituted C1 to 6 alkoxy group may be substituted) For example, 2-benzothienylmethyl group, 2- (3-benzothienyl) ethyl group, 1- (4-benzothienyl) ethyl group, 3- (5-benzothienyl) propyl group, 4- (6-benzo Thienyl) butyl group, 5- (7-benzothienyl) pentyl group, 6- (2-benzothienyl) hexyl group, 2-methyl-3- (3-benzothienyl) propyl group, 1,1-dimethyl-2- (2-benzothienyl) ethyl group, 4-fluoro-2-benzothienylmethyl group, 5-fluoro-2-benzothienylmethyl group, 6-fluoro-2-benzo Enylmethyl group, 7-fluoro-2-benzothienylmethyl group, 4-chloro-2-benzothienylmethyl group, 5-chloro-2-benzothienylmethyl group, 6-chloro-2-benzothienylmethyl group, 7-chloro -2-benzothienylmethyl group, 4-bromo-2-benzothienylmethyl group, 5-bromo-2-benzothienylmethyl group, 6-bromo-2-benzothienylmethyl group, 7-bromo-2-benzothienylmethyl group Group, 4-methoxy-2-benzothienylmethyl group, 5-methoxy-2-benzothienylmethyl group, 6-methoxy-2-benzothienylmethyl group, 6,7-dimethoxy-2-benzothienylmethyl group, 3, 6,7-trimethoxy-2-benzothienylmethyl group, 7-methoxy-2-benzothienylmethyl group, 4-trifluoro 4-hydroxy-2-benzothienylmethyl group, 5-trifluoromethoxy-2-benzothienylmethyl group, 6-trifluoromethoxy-2-benzothienylmethyl group, 7-trifluoromethoxy-2-benzothienylmethyl group, 4- Ethoxy-2-benzothienylmethyl group, 5-ethoxy-2-benzothienylmethyl group, 6-ethoxy-2-benzothienylmethyl group, 7-ethoxy-2-benzothienylmethyl group, 4-chloro-5-trifluoro Methoxy-2-benzothienylmethyl group, 6-chloro-5-trifluoromethoxy-2-benzothienylmethyl group, 7-chloro-5-trifluoromethoxy-2-benzothienylmethyl group, 3-benzothienylmethyl group, 4-fluoro-3-benzothienylmethyl group, 5-fluoro-3-benzothienyl Methyl group, 6-fluoro-3-benzothienylmethyl group, 7-fluoro-3-benzothienylmethyl group, 4-chloro-3-benzothienylmethyl group, 5-chloro-3-benzothienylmethyl group, 6-chloro -3-benzothienylmethyl group, 7-chloro-3-benzothienylmethyl group, 4-bromo-3-benzothienylmethyl group, 5-bromo-3-benzothienylmethyl group, 6-bromo-3-benzothienylmethyl Group, 7-bromo-3-benzothienylmethyl group, 4-methoxy-3-benzothienylmethyl group, 5-methoxy-3-benzothienylmethyl group, 6-methoxy-3-benzothienylmethyl group, 7-methoxy- 3-benzothienylmethyl group, 4-trifluoromethoxy-3-benzothienylmethyl group, 5-trifluoromethoxy-3- Nzothienylmethyl group, 6-trifluoromethoxy-3-benzothienylmethyl group, 7-trifluoromethoxy-3-benzothienylmethyl group, 4-ethoxy-3-benzothienylmethyl group, 5-ethoxy-3-benzo Thienylmethyl group, 6-ethoxy-3-benzothienylmethyl group, 7-ethoxy-3-benzothienylmethyl group, 4-chloro-5-trifluoromethoxy-3-benzothienylmethyl group, 6-chloro-5-trithiotrimethylmethyl group Fluoromethoxy-3-benzothienylmethyl group, 7-chloro-5-trifluoromethoxy-3-benzothienylmethyl group, 2- (2-benzothienyl) ethyl group, 3- (2-benzothienyl) propyl group, 4 -(2-benzothienyl) butyl group, 5- (2-benzothienyl) pentyl group, 6- (2-benzothie) Hexyl group, 2- (3-benzothienyl) ethyl group, 3- (3-benzothienyl) propyl group, 4- (3-benzothienyl) butyl group, 5- (3-benzothienyl) pentyl group, 6 -(3-benzothienyl) hexyl group, 2- (5-chloro-2-benzothienyl) ethyl group, 3- (5-chloro-2-benzothienyl) propyl group, 4- (5-chloro-2-benzo) group Thienyl) butyl group, 5- (5-chloro-2-benzothienyl) pentyl group, 6- (5-chloro-2-benzothienyl) hexyl group, 2- (5-chloro-3-benzothienyl) ethyl group, 3- (5-chloro-3-benzothienyl) propyl group, 4- (5-chloro-3-benzothienyl) butyl group, 5- (5-chloro-3-benzothienyl) pentyl group, 6- (5-chloro-3-benzothienyl) propyl group Chloro-3- A benzothienyl C1-6 alkyl group such as a benzothienyl) hexyl group (in the benzothiophene ring, a group selected from the group consisting of a halogen atom and a halogen substituted or unsubstituted C1-6 alkoxy group is substituted by 1 to 3) May be mentioned).

  As a thienyl C1-6 alkyl group which may be substituted by a halogen atom on the thiophene ring, for example, 2-thienylmethyl group, 2- (3-thienyl) ethyl group, 1- (2-thienyl) ethyl group, 3- (2-thienyl) propyl group, 4- (3-thienyl) butyl group, 5- (2-thienyl) pentyl group, 6- (2-thienyl) hexyl group, 2-methyl-3- (3-thienyl group ) Propyl group, 1,1-dimethyl-2- (2-thienyl) ethyl group, 3-fluoro-2-thienylmethyl group, 4-fluoro-2-thienylmethyl group, 3,4-difluoro-2-thienylmethyl Group, 3,4,5-trichloro-2-thienylmethyl group, 5-fluoro-2-thienylmethyl group, 3-chloro-2-thienylmethyl group, 4-chloro-2-thienylmethyl group, 5-chloro 2-thienylmethyl group, 3-bromo-2-thienylmethyl group, 4-bromo-2-thienylmethyl group, 5-bromo-2-thienylmethyl group, 3-thienylmethyl group, 2-fluoro-3-thienylmethyl Group, 4-fluoro-3-thienylmethyl group, 5-fluoro-3-thienylmethyl group, 2-chloro-3-thienylmethyl group, 4-chloro-3-thienylmethyl group, 5-chloro-3-thienylmethyl group Group, 2-bromo-3-thienylmethyl group, 4-bromo-3-thienylmethyl group, 5-iodo-3-thienylmethyl group, 2- (5-chloro-2-thienyl) ethyl group, 3- (5) -Chloro-2-thienyl) propyl group, 4- (5-chloro-2-thienyl) butyl group, 5- (5-chloro-2-thienyl) pentyl group, 6- (5-chloro-2-thienyl) phenyl group Sil group, 2- (5-chloro-3-thienyl) ethyl group, 3- (5-chloro-3-thienyl) propyl group, 4- (5-chloro-3-thienyl) butyl group, 5- (5-) To cite a thienyl C1-6 alkyl group which may have one to three halogen atoms substituted on a thiophene ring such as chloro-3-thienyl) pentyl group, 6- (5-chloro-3-thienyl) hexyl group Can.

  Examples of the benzothiazolyl C1-6 alkyl group include a benzothiazol-2-ylmethyl group, a benzothiazol-4-ylmethyl group, a benzothiazol-5-ylmethyl group, a benzothiazol-6-ylmethyl group and a benzothiazol-7-ylmethyl group. , 2- (benzothiazol-4-yl) ethyl group, (benzothiazol-5-yl) methyl group, 2- (benzothiazol-6-yl) ethyl group, 2- (benzothiazol-7-yl) ethyl group , 3- (benzothiazol-4-yl) propyl group, 3- (benzothiazol-5-yl) propyl group, 3- (benzothiazol-6-yl) propyl group, 3- (benzothiazol-7-yl) Propyl group, 4- (benzothiazol-2-yl) butyl group, 4- (benzothiazol-4-yl) Ethyl, 4- (benzothiazol-5-yl) butyl, 4- (benzothiazol-6-yl) butyl, 4- (benzothiazol-7-yl) butyl, 5- (benzothiazole-2-) Pentyl), 5- (benzothiazol-4-yl) pentyl, 5- (benzothiazol-5-yl) pentyl, 5- (benzothiazol-6-yl) pentyl, 5- (benzothiazol-) 7-yl) pentyl group, 6- (benzothiazol-2-yl) hexyl group, 6- (benzothiazol-4-yl) hexyl group, 6- (benzothiazol-5-yl) hexyl group, 6- (benzo) Thiazol-6-yl) hexyl group, 6- (benzothiazol-7-yl) hexyl group and the like can be mentioned.

  As the benzofuryl C1-6 alkyl group which the halogen atom may substitute on the benzofuran ring, for example, 2-benzofurylmethyl group, 2- (3-benzofuryl) ethyl group, 1- (4-benzofuryl) ethyl group 3- (5-benzofuryl) propyl group, 4- (6-benzofuryl) butyl group, 5- (7-benzofuryl) pentyl group, 6- (2-benzofuryl) hexyl group, 2-methyl-3- (3-) Benzofuryl) propyl, 1,1-dimethyl-2- (2-benzofuryl) ethyl, 4-fluoro-2-benzofurylmethyl, 5-fluoro-2-benzofurylmethyl, 6-fluoro-2-benzo Furylmethyl group, 7-fluoro-2-benzofurylmethyl group, 4-chloro-2-benzofurylmethyl group, 5-chloro-2-benzofurylmethyl , 6-chloro-2-benzofurylmethyl group, 7-chloro-2-benzofurylmethyl group, 4-bromo-2-benzofurylmethyl group, 5-bromo-2-benzofurylmethyl group, 6-bromo-2 -Benzofurylmethyl group, 7-bromo-2-benzofurylmethyl group, 4-iodo-2-benzofurylmethyl group, 5-iodo-2-benzofurylmethyl group, 6-iodo-2-benzofurylmethyl group, 7-iodo-2-benzofurylmethyl group, 4-fluoro-3-benzofurylmethyl group, 5-fluoro-3-benzofurylmethyl group, 5,6-difluoro-2-benzofurylmethyl group, 7-fluoro- 3-benzofurylmethyl group, 4-chloro-3-benzofurylmethyl group, 3,5,6-trichloro-3-benzofurylmethyl group, 6-chloro-3-benzofuryl Ethyl, 7-chloro-3-benzofurylmethyl, 4-bromo-3-benzofurylmethyl, 5-bromo-3-benzofurylmethyl, 6-bromo-3-benzofurylmethyl, 7-bromo -3-benzofurylmethyl group, 4-iodo-3-benzofurylmethyl group, 5-iodo-3-benzofurylmethyl group, 6-iodo-3-benzofurylmethyl group, 7-iodo-3-benzofurylmethyl group Mention may be made of a benzofuryl C1-6 alkyl group which may be substituted by 1 to 3 halogen atoms as a substituent on a benzofuran ring such as a group.

  Examples of the indolinyl C1-6 alkyl group (wherein at least one group selected from the group consisting of a C1-6 alkyl group and an oxo group may be substituted on the indoline ring) include, for example, 2-indolinylmethyl Group, 2- (3-indolinyl) ethyl group, 1- (4-indolinyl) ethyl group, 3- (5-indolinyl) propyl group, 4- (6-indolinyl) butyl group, 5- (7-indolinyl) pentyl Group, 6- (1-indolinyl) hexyl group, 2-methyl-3- (3-indolinyl) propyl group, 1,1-dimethyl-2- (2-indolinyl) ethyl group, 3,3-dimethyl-5- Indolinylmethyl group, 1,3,3-trimethyl-5-indolinylmethyl group, 1-ethyl-3,3-dimethyl-5-indolinylmethyl group, 1-methyl-5-indo Nylmethyl group, 1,3-dimethyl-5-indolinylmethyl group, 1,3,3,6,7-pentamethyl-5-indolinylmethyl group, 3,3-dimethyl-1- (n-propyl) -5 -Indolinylmethyl group, 3,3-dimethyl-1- (isopropyl) -5-indolinylmethyl group, 1- (n-butyl) -3,3-dimethyl-5-indolinylmethyl group, 1- (sec) -Butyl) -3,3-dimethyl-5-indolinylmethyl, 1- (tert-butyl) -3,3-dimethyl-5-indolinylmethyl, 1- (n-pentyl) -3,3- Dimethyl-5-indolinylmethyl group, 1- (n-hexyl) -3,3-dimethyl-5-indolinylmethyl group, 3,3-dimethyl-2-oxo-5-indolinylmethyl group, 1,3 , 3-trimethyl- -Oxo-5-indolinylmethyl group, 1-ethyl-3,3-dimethyl-2-oxo-5-indolinylmethyl group, 3,3-dimethyl-2-oxo-1- (n-propyl) -5 -Indolinylmethyl group, 3,3-dimethyl-2-oxo-1- (isopropyl) -5-indolinylmethyl group, 1- (n-butyl) -3,3-dimethyl-2-oxo-5-indoli Nylmethyl group, 1- (sec-butyl) -3,3-dimethyl-2-oxo-5-indolinylmethyl group, 1- (tert-butyl) -3,3-dimethyl-2-oxo-5-indoli Nylmethyl group, 1- (n-pentyl) -3,3-dimethyl-2-oxo-5-indolinylmethyl group, 1- (n-hexyl) -3,3-dimethyl-2-oxo-5-indoli Nylmethyl group, 2-oxo- Examples include indolinyl C1-6 alkyl groups such as 5-indolinylmethyl group (1 to 5 groups selected from the group consisting of C1-6 alkyl groups and oxo groups may be substituted on the indoline ring) be able to.

  As a benzoxazolyl C1-6 alkyl group (The benzoxazole ring may be substituted by at least one group selected from the group consisting of a halogen atom, a C1-6 alkyl group and an oxo group) For example, benzoxazol-2-ylmethyl group, benzoxazol-4-ylmethyl group, benzoxazol-5-ylmethyl group, benzoxazol-6-ylmethyl group, benzoxazol-7-ylmethyl group, 2- (benzoxazole-2-yl group) -Ethyl group, 1- (benzoxazol-4-yl) ethyl group, 3- (benzoxazol-5-yl) propyl group, 4- (benzoxazol-6-yl) butyl group, 5- (benzoxazole-) 7-yl) pentyl group, 6- (benzoxazol-2-yl) hexyl group, 2-methyl -3- (benzoxazol-4-yl) propyl, 1,1-dimethyl-2- (benzoxazol-5-yl) ethyl, 2,5-dimethylbenzoxazol-4-ylmethyl, 2,5, 6-trimethylbenzoxazol-4-ylmethyl group, 4,5-dichlorobenzoxazol-4-ylmethyl group, 2,4,5-trichlorobenzoxazol-4-ylmethyl group, (2,3-dihydro-2-oxo- Benzoxazol-3-yl) methyl group, (2,3-dihydro-2-oxo-benzoxazol-4-yl) methyl group, (2,3-dihydro-2-oxo-benzoxazol-5-yl) methyl group Group, (2,3-dihydro-2-oxo-benzoxazol-6-yl) methyl group, (2,3-dihydro-2-oxo-be) Zooxazol-7-yl) methyl group, 2- (benzoxazol-4-yl) ethyl group, (benzoxazol-5-yl) methyl group, 2- (benzoxazol-6-yl) ethyl group, 2- (benzoxazol-4-yl) ethyl group Benzoxazol-7-yl) ethyl group, 2- (2,3-dihydro-2-oxo-benzoxazol-3-yl) ethyl group, 2- (2,3-dihydro-2-oxo-benzoxazole-4) -Yl) ethyl group, 2- (2,3-dihydro-2-oxo-benzoxazol-5-yl) ethyl group, 2- (2,3-dihydro-2-oxo-benzoxazol-6-yl) ethyl Group, 2- (2,3-dihydro-2-oxo-benzoxazol-7-yl) ethyl group, 3- (benzoxazol-2-yl) propyl group, 3- (benzoxazool) R-4-yl) propyl group, 3- (benzoxazol-6-yl) propyl group, 3- (benzoxazol-7-yl) propyl group, 3- (2,3-dihydro-2-oxo-benzoxazole) -3-yl) propyl group, 3- (2,3-dihydro-2-oxo-benzoxazol-4-yl) propyl group, 3- (2,3-dihydro-2-oxo-benzoxazol-5-yl) ) Propyl group, 3- (2,3-dihydro-2-oxo-benzoxazol-6-yl) propyl group, 3- (2,3-dihydro-2-oxo-benzoxazol-7-yl) propyl group, 4- (benzoxazol-2-yl) butyl group, 4- (benzoxazol-4-yl) butyl group, 4- (benzoxazol-5-yl) butyl group, 4- (benzoxazol-2-yl) butyl group Zol-7-yl) butyl group, 4- (2,3-dihydro-2-oxo-benzoxazol-3-yl) butyl group, 4- (2,3-dihydro-2-oxo-benzoxazole-4- 4 Yl) butyl group, 4- (2,3-dihydro-2-oxo-benzoxazol-5-yl) butyl group, 4- (2,3-dihydro-2-oxo-benzoxazol-6-yl) butyl group 4- (2,3-dihydro-2-oxo-benzoxazol-7-yl) butyl group, 5- (benzoxazol-2-yl) pentyl group, 5- (benzoxazol-4-yl) pentyl group, 5- (benzoxazol-5-yl) pentyl group, 5- (benzoxazol-6-yl) pentyl group, 5- (2,3-dihydro-2-oxo-benzoxazol-3-yl) A pentyl group, 5- (2,3-dihydro-2-oxo-benzoxazol-4-yl) pentyl group, 5- (2,3-dihydro-2-oxo-benzoxazol-5-yl) pentyl group, 5 -(2,3-dihydro-2-oxo-benzoxazol-6-yl) pentyl group, 5- (2,3-dihydro-2-oxo-benzoxazol-7-yl) pentyl group, 6- (benzoxazole) -4-yl) hexyl group, 6- (benzoxazol-5-yl) hexyl group, 6- (benzoxazol-6-yl) hexyl group, 6- (benzoxazol-7-yl) hexyl group, 6- (6) 2,3-Dihydro-2-oxo-benzoxazol-3-yl) hexyl group, 6- (2,3-dihydro-2-oxo-benzoxazol-4-yl) hexy 6- (2,3-dihydro-2-oxo-benzoxazol-5-yl) hexyl group, 6- (2,3-dihydro-2-oxo-benzoxazol-6-yl) hexyl group, 6 -(2,3-dihydro-2-oxo-benzoxazol-7-yl) hexyl group, 2-methylbenzoxazol-4-ylmethyl group, 2-methylbenzoxazol-5-ylmethyl group, 2-methylbenzoxazol-6-ylmethyl group, 4-methylbenzoxazol-2-ylmethyl group, 5-methylbenzoxazol-2-ylmethyl group, 6-methylbenzoxazole- 2-ylmethyl group, 7-methylbenzoxazol-2-ylmethyl group, 2-ethylbenzoxazol-4-ylmethyl group, 2-ethylbenzoxazol-5-ylmethyl , 2-ethylbenzoxazol-6-ylmethyl group, 2-n-propylbenzoxazol-4-ylmethyl group, 2-n-propylbenzoxazol-5-ylmethyl group, 2-n -Propylbenzoxazol-6-ylmethyl group, 4-fluorobenzoxazol-2-ylmethyl group, 5-fluoro-2-benzoxazolylmethyl group, 6-fluoro-2-benzoxazolyl Methyl group, 7-fluorobenzoxazol-2-ylmethyl group, 4-chlorobenzoxazol-2-ylmethyl group, 5-chloro-2-benzoxazol-2-ylmethyl group, 6-chloro- 2-benzoxazol-2-ylmethyl group, 7-chloro-2-benzoxazol-2-ylmethyl group, 4-bromo-2-benzoxazol-2-ylmethyl group , 5-bromo-2-benzoxazol-2-ylmethyl group, 6-bromo-2-benzoxazol-2-ylmethyl group, 7-bromo-2-benzoxazol-2-ylmethyl group, 4-fluoro- 2-oxo-2,3-dihydrobenzoxazol-3-ylmethyl group, 5-fluoro-2-oxo-2,3-dihydrobenzoxazol-3-ylmethyl group, 6-fluoro-2- Oxo-2,3-dihydrobenzoxazol-3-ylmethyl group, 7-fluoro-2-oxo-2,3-dihydrobenzoxazol-3-ylmethyl group, 4-chloro-2-oxo- 2,3-Dihydrobenzoxazol-3-ylmethyl group, 5-chloro-2-oxo-2,3-dihydrobenzoxazol-3-ylmethyl group, 6-chloro-2-oxo-2 , 3-dihydrobenzoxazol-3-ylmethyl group, 7-chloro-2-oxo-2,3-dihydrobenzoxazol-3-ylmethyl group, 4-bromo-2-oxo-2,3 -Dihydrobenzoxazol-3-ylmethyl group, 5-bromo-2-oxo-2,3-dihydrobenzoxazol-3-ylmethyl group, 6-bromo-2-oxo-2,3-dihydro Benzoxazol-3-ylmethyl group, 7-bromo-2-oxo-2,3-dihydrobenzoxazol-3-ylmethyl group, 4-fluoro-2-oxo-2,3-dihydrobenzoxa Zol-5-ylmethyl group, 5-fluoro-2-oxo-2,3-dihydrobenzoxazol-5-ylmethyl group, 6-fluoro-2-oxo-2,3-dihydrobenzoxazo- Le-5 Ylmethyl group, 7-fluoro-2-oxo-2,3-dihydrobenzoxazol-5-ylmethyl group, 4-chloro-2-oxo-2,3-dihydrobenzoxazol-5-ylmethyl group 5-chloro-2-oxo-2,3-dihydrobenzoxazol-5-ylmethyl group, 6-chloro-2-oxo-2,3-dihydrobenzoxazol-5-ylmethyl group, 7 -Chloro-2-oxo-2,3-dihydrobenzoxazol-5-ylmethyl group, 4-bromo-2-oxo-2,3-dihydrobenzoxazol-5-ylmethyl group, 5-bromo -2-oxo-2,3-dihydrobenzoxazol-5-ylmethyl group, 6-bromo-2-oxo-2,3-dihydrobenzoxazol-5-ylmethyl group, 7-bromo-2 -Oxo- , 3-dihydrobenzoxazol-5-ylmethyl group, 4-fluoro-2-oxo-2,3-dihydrobenzoxazol-6-ylmethyl group, 5-fluoro-2-oxo-2,3 -Dihydrobenzoxazol-6-ylmethyl group, 6-fluoro-2-oxo-2,3-dihydrobenzoxazol-6-ylmethyl group, 7-fluoro-2-oxo-2,3-dihydro Benzoxazol-6-ylmethyl group, 4-chloro-2-oxo-2,3-dihydrobenzoxazol-6-ylmethyl group, 5-chloro-2-oxo-2,3-dihydrobenzoxa Zol-6-ylmethyl group, 6-chloro-2-oxo-2,3-dihydrobenzoxazol-6-ylmethyl group, 7-chloro-2-oxo-2,3-dihydrobenzoxazo- Rule 6-ylmethyl group, 4-bromo-2-oxo-2,3-dihydrobenzoxazol-6-ylmethyl group, 5-bromo-2-oxo-2,3-dihydrobenzoxazole-6- Ylmethyl group, 6-bromo-2-oxo-2,3-dihydrobenzoxazol-6-ylmethyl group, 7-bromo-2-oxo-2,3-dihydrobenzoxazol-6-ylmethyl group A benzoxazolyl C.sub.1-6 alkyl group (such as a halogen atom, a C.sub.1-6 alkyl group, and a group selected from the group consisting of oxo groups may be substituted on the benzoxazole ring). It can be mentioned.

  As a clomenyl C1-6 alkyl group, for example, 2-chromenyl methyl group, 3-chromenyl methyl group, 4-chromenyl methyl group, 5-chromenyl methyl group, 6-chromenyl methyl group, 7-chromenyl group Methyl group, 8-chromenylmethyl group, 2- (2-chromenyl) ethyl group, 1- (3-chromenyl) ethyl group, 3- (4-chromenyl) propyl group, 4- (5-chromenyl) butyl group, 5- (6-chromenyl) pentyl group, 6- (7-chromenyl) hexyl group, 2-methyl-3- (8-chromenyl) propyl group, 1,1-dimethyl-2- (6-chromenyl) ethyl group, etc. Can be mentioned.

  1,2,3,4-Tetrahydroquinolyl C1-6 alkyl group (On the quinoline ring, at least one selected from the group consisting of a C1-6 alkyl group and an oxo group may be substituted) For example, (1,2,3,4-tetrahydro-6-quinolyl) methyl group, 2- (1,2,3,4-tetrahydro-2-quinolyl) ethyl group, 1- (1,2,2, 3,4-tetrahydro-1-quinolyl) ethyl group, 3- (1,2,3,4-tetrahydro-3-quinolyl) propyl group, 4- (1,2,3,4-tetrahydro-4-quinolyl) Butyl group, 5- (1,2,3,4-tetrahydro-5-quinolyl) pentyl group, 6- (1,2,3,4-tetrahydro-6-quinolyl) hexyl group, 2-methyl-3- ( 1,2,3,4-Tetrahydro-7-quinolyl) group Pill group, 1,1-dimethyl-2- (1,2,3,4-tetrahydro-8-quinolyl) ethyl group, 2-oxo-1,2,3,4-tetrahydro-6-quinolylmethyl group, 4- Methyl-1,2,3,4-tetrahydro-6-quinolylmethyl group, 4-oxo-1,2,3,4-tetrahydro-6-quinolylmethyl group, 4,6-dimethyl-1,2,3,4- Tetrahydro-5-quinolylmethyl group, 1,4,8-trimethyl-1,2,3,4-tetrahydro-6-quinolylmethyl group, 1-methyl-2-oxo-1,2,3,4-tetrahydro-6- Quinolylmethyl group, 1-ethyl-2-oxo-1,2,3,4-tetrahydro-6-quinolylmethyl group, 2-oxo-1- (n-propyl) -1,2,3,4-tetrahydro-6- Quinolylmethyl group, 2 Oxo-1- (isopropyl) -1,2,3,4-tetrahydro-6-quinolylmethyl group, 1- (n-butyl) -2-oxo-1,2,3,4-tetrahydro-6-quinolylmethyl group, 1- (sec-butyl) -2-oxo-1,2,3,4-tetrahydro-6-quinolylmethyl group, 1- (tert-butyl) -2-oxo-1,2,3,4-tetrahydro-6 -Quinolylmethyl group, 1- (n-pentyl) -2-oxo-1,2,3,4-tetrahydro-6-quinolylmethyl group, 1- (n-hexyl) -2-oxo-1,2,3,4 -Tetrahydro-6-quinolylmethyl group, 2- (2-oxo-1,2,3,4-tetrahydro-6-quinolyl) ethyl group, 3- (2-oxo-1,2,3,4-tetrahydro-6) -Quinolyl) propyl group, 4- (2-oxo-1,2,3,4-tetrahydro-6-quinolyl) butyl group, 5- (2-oxo-1,2,3,4-tetrahydro-6-quinolyl) pentyl group, 6- (2 -Oxo-1,2,3,4-tetrahydro-6-quinolyl) hexyl group, 2- (1-methyl-2-oxo-1,2,3,4-tetrahydro-6-quinolyl) ethyl group, 3- (1-Methyl-2-oxo-1,2,3,4-tetrahydro-6-quinolyl) propyl group, 4- (1-methyl-2-oxo-1,2,3,4-tetrahydro-6-quinolyl ) Butyl group, 5- (1-methyl-2-oxo-1,2,3,4-tetrahydro-6-quinolyl) pentyl group, 6- (1-methyl-2-oxo-1,2,3,4 1,2,3,4-Tetra, such as -Tetrahydro-6-quinolyl) hexyl group Dorokinoriru Cl to 6 (On quinoline ring, Cl to 6 alkyl and a group selected from oxo group consisting group may have one to three substituents) alkyl group can be exemplified.

  A thiazolyl C1-6 alkyl group (on the thiazole ring, at least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted phenyl group and a C1-6 alkyl group may be substituted) As, for example, 2-thiazolylmethyl group, 4-thiazolylmethyl group, 5-thiazolylmethyl group, 2- (2-thiazolyl) ethyl group, 1- (4-thiazolyl) ethyl group, 3- (5-thiazolyl) propyl group, 4- (2-thiazolyl) butyl group, 5- (4-thiazolyl) pentyl group, 6- (5-thiazolyl) hexyl group, 2-methyl-3- (2-thiazolyl) propyl group, 1,1-dimethyl- 2- (4-thiazolyl) ethyl group, 2-chloro-4-thiazolylmethyl group, 2,5-dichloro-4-thiazolylmethyl group, 2-chloro-5-thiol Zorylmethyl group, 2-chloro-6-thiazolylmethyl group, 6-chloro-2-thiazolylmethyl group, 5-chloro-2-thiazolylmethyl group, 4-chloro-2-thiazolylmethyl group, 5-chloro-4-thiazolylmethyl group, 4- Chloro-5-thiazolylmethyl group, 2-ethyl-4-thiazolylmethyl group, 2,5-dimethyl-4-thiazolylmethyl group 2-methyl-4-thiazolylmethyl group, 2-methyl-5-thiazolylmethyl group, 2-methyl-6- Thiazolylmethyl group, 6-methyl-2-thiazolylmethyl group, 5-methyl-2-thiazolylmethyl group, 4-methyl-2-thiazolylmethyl group, 5-methyl-4-thiazolylmethyl group, 4-methyl-5-thiazolylmethyl group, 2- Ethyl-4-thiazolylmethyl group, 2-ethyl-5-thiazolylmethyl , 2-ethyl-6-thiazolylmethyl group, 6-ethyl-2-thiazolylmethyl group, 5-ethyl-2-thiazolylmethyl group, 4-ethyl-2-thiazolylmethyl group, 5-ethyl-4-thiazolylmethyl group, 4-ethyl- 5-thiazolylmethyl group, 2-phenyl-4-thiazolylmethyl group, 2-phenyl-5-thiazolylmethyl group, 2-phenyl-6-thiazolylmethyl group, 6-phenyl-2-thiazolylmethyl group, 5-phenyl-2-thiazolylmethyl group, 4-phenyl-2-thiazolylmethyl group, 5-phenyl-4-thiazolylmethyl group, 4-phenyl-5-thiazolylmethyl group, 5- (2-fluorophenyl) -2-thiazolylmethyl group, 5- (2,4-difluorophenyl) ) -4-thiazolylmethyl group, 4- (2-fluorophenyl)- 5-thiazolylmethyl group, 2- (2-fluorophenyl) -4-thiazolylmethyl group, 2- (2-fluorophenyl) -5-thiazolylmethyl group, 2- (3-fluorophenyl) -4-thiazolylmethyl group, 2- (2- (2-fluorophenyl) -4-thiazolylmethyl group) 3-fluorophenyl) -5-thiazolylmethyl group, 2- (4-fluorophenyl) -4-thiazolylmethyl group, 4- (2-fluorophenyl) -5-thiazolylmethyl group, 2- (2-chlorophenyl) -4-thiazolylmethyl Group, 2- (2-chlorophenyl) -5-thiazolylmethyl group, 2- (3-chlorophenyl) -4-thiazolylmethyl group, 2- (2-fluorophenyl) -5-thiazolylmethyl group, 2- (4-chlorophenyl)- 4-thiazolyl methyl group, 2- (4-chlorophenyl) -5-thiazolyl methyl group, etc. Zoryl C1-6 alkyl group (1 to 2 groups selected from the group consisting of halogen atoms, 1 to 5 halogen atoms or substituted or unsubstituted phenyl groups and C1 to 6 alkyl groups on the thiazole ring May be mentioned).

  As a tetrazolyl C1-6 alkyl group (wherein at least one group selected from the group consisting of a halogen-substituted or unsubstituted phenyl group and a C1-6 alkyl group may be substituted on the tetrazole ring), For example, 5- (1H) -tetrazolylmethyl group, 2- (5- (1H) -tetrazolyl) ethyl group, 1- (5- (1H) -tetrazolyl) ethyl group, 3- (5- (1H) group -Tetrazolyl) propyl group, 4- (5- (1H) -tetrazolyl) butyl group, 5- (5- (1H) -tetrazolyl) pentyl group, 6- (5- (1H) -tetrazolyl) hexyl group, 2- Methyl-3- (5- (1H) -tetrazolyl) propyl group, 1,1-dimethyl-2- (5- (1H) -tetrazolyl) ethyl group, 1-methyl-5- (1H) -tetrazolylmethyl Group 1-ethyl-5- (1H) -tetrazolylmethyl group, 1-propyl-5- (1H) -tetrazolylmethyl group, 1-butyl-5- (1H) -tetrazolylmethyl group, 1- Pentyl-5- (1H) -tetrazolylmethyl group, 1-hexyl-5- (1H) -tetrazolylmethyl group, 1-phenyl-5- (1H) -tetrazolylmethyl group, 1- (2) -Fluorophenyl) -5- (1H) -tetrazolylmethyl group, 1- (3-fluorophenyl) -5- (1H) -tetrazolylmethyl group, 1- (2,3,4,5,6) -Pentafluorophenyl) -5- (1H) -tetrazolylmethyl group, 1- (2-chlorophenyl) -5- (1H) -tetrazolylmethyl group, 1- (3-chlorophenyl) -5- (1H) ) -Tetrazolylmethyl group, 1- (2,4,6-to) Chlorophenyl) -5- (1H) -tetrazolylmethyl group, 1- (2-bromophenyl) -5- (1H) -tetrazolylmethyl group, 1- (2,3-dibromophenyl) -5- (4) 1H) -tetrazolylmethyl group, 1- (4-bromophenyl) -5- (1H) -tetrazolylmethyl group, 2- (1-methyl-5- (1H) -tetrazolyl) ethyl group, 2- (1-ethyl-5- (1H) -tetrazolyl) ethyl group, 2- (1-propyl-5- (1H) -tetrazolyl) ethyl group, 2- (1-butyl-5- (1H) -tetrazolyl) ethyl Group, 2- (1-pentyl-5- (1H) -tetrazolyl) ethyl group, 2- (1-hexyl-5- (1H) -tetrazolyl) ethyl group, 2- (1-phenyl-5- (1H) -Tetrazolyl) ethyl group, 2- (1- (2) -Fluorophenyl) -5- (1H) -tetrazolyl) ethyl group, 2- (1- (3-fluorophenyl) -5- (1H) -tetrazolyl) ethyl group, 2- (1- (4-fluorophenyl) group -5- (1H) -tetrazolyl) ethyl group, 2- (1- (2-chlorophenyl) -5- (1H) -tetrazolyl) ethyl group, 2- (1- (3-chlorophenyl) -5- (1H) -Tetrazolyl) ethyl group, 2- (1- (4-chlorophenyl) -5- (1H) -tetrazolyl) ethyl group, 2- (1- (2-bromophenyl) -5- (1H) -tetrazolyl) ethyl group Tetrazolyl C1 such as 2- (1- (3-bromophenyl) -5- (1H) -tetrazolyl) ethyl group, 2- (1- (4-bromophenyl) -5- (1H) -tetrazolyl) ethyl group, etc. ~ 6 al Group (on the tetrazole ring, a halogen atom may be substituted with a group selected from the group consisting of a substituted or unsubstituted phenyl group and a C1-6 alkyl group of 1 to 5). .

A piperidine ring or a 1,2,3,6-tetrahydropyridine ring (a piperidine ring and a 1,2,3,3, ring formed by R ^{32 ′} and R ^{33 ′} being bonded to each other via another carbon atom together with the adjacent nitrogen atom) A phenyl group may be substituted on the 6-tetrahydropyridine ring, and at least one group selected from the group consisting of a halogen atom and a halogen substituted or unsubstituted C1-6 alkyl group may be substituted on the phenyl group. And the like, for example, piperidine, 4-phenylpiperidine, 4- (2-fluorophenyl) piperidine, 4- (3-fluorophenyl) piperidine, 4- (3-fluoro-4-triyl). Fluoromethylphenyl) piperidine, 4- (3,4,5-trichlorophenyl) piperidine, 4- (2,3,4,5,6-pentafluorophenyl) Peridine, 4- (2,4-dimethylphenyl) piperidine, 4- (2,4,6-trimethylphenyl) piperidine, 4- (2-trifluoromethyl-4-methylphenyl) piperidine, 4- (4-fluoro) Phenyl) piperidine, 4- (3,4-difluorophenyl) piperidine, 4- (2-chlorophenyl) piperidine, 4- (3-chlorophenyl) piperidine, 4- (4-chlorophenyl) piperidine, 4- (3,4-chlorophenyl) piperidine Dichlorophenyl) piperidine, 4- (2-methylphenyl) piperidine, 4- (3-methylphenyl) piperidine, 4- (4-methylphenyl) piperidine, 4- (2-trifluoromethylphenyl) piperidine, 4- (3 -Trifluoromethylphenyl) piperidine, 4- (4-trifluoromethylphenyl) pipe Lysine, 4-phenyl-1,2,3,6-tetrahydropyridine, 4- (2-fluorophenyl) -1,2,3,6-tetrahydropyridine, 4- (3-fluorophenyl) -1,2,3, 3,6-tetrahydropyridine, 4- (4-fluorophenyl) -1,2,3,6-tetrahydropyridine, 4- (3,4-difluorophenyl) -1,2,3,6-tetrahydropyridine, 4 -(2-chlorophenyl) -1,2,3,6-tetrahydropyridine, 4- (3-chlorophenyl) -1,2,3,6-tetrahydropyridine, 4- (4-chlorophenyl) -1,2,3 , 6-tetrahydropyridine, 4- (3,4-dichlorophenyl) -1,2,3,6-tetrahydropyridine, 4- (2-methylphenyl) -1,2,3,6-tetrahydropyridine Gin, 4- (3-methylphenyl) -1,2,3,6-tetrahydropyridine, 4- (4-methylphenyl) -1,2,3,6-tetrahydropyridine, 4- (2-trifluoromethyl) Phenyl) -1,2,3,6-tetrahydropyridine, 4- (3-trifluoromethylphenyl) -1,2,3,6-tetrahydropyridine, 4- (4-trifluoromethylphenyl) -1,2 , 3,6-tetrahydropyridine, 4- (3-fluoro-4-trifluoromethylphenyl) -1,2,3,6-tetrahydropyridine, 4- (3,4,5-trichlorophenyl) -1,2 , 3,6-tetrahydropyridine, 4- (2,3,4,5,6-pentafluorophenyl) -1,2,3,6-tetrahydropyridine, 4- (2,4-dimethylphenyl) 1,2,3,6-tetrahydropyridine, 4- (2,4,6-trimethylphenyl) -1,2,3,6-tetrahydropyridine, 4- (2-trifluoromethyl-4-methylphenyl)- A piperidine ring such as 1,2,3,6-tetrahydropyridine or a 1,2,3,6-tetrahydropyridine ring (a phenyl group is substituted on the piperidine ring or on the 1,2,3,6-tetrahydropyridine ring The phenyl group may be substituted by 1 to 5, preferably 1 to 3 groups selected from the group consisting of halogen atoms and halogen-substituted or unsubstituted C1-6 alkyl groups. . Can be mentioned.

  Examples of the C3-8 cycloalkenyl group include cyclopropenyl group, cyclobutenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, cyclooctenyl group and the like.

  Phenyl group [on the phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group, a halogen-substituted or unsubstituted C1-6 alkoxy group, a C1-4 alkylenedioxy group, a C1-6 alkylsulfonyl group At least one of a group selected from the group consisting of a halogen-substituted or unsubstituted C1-6 alkylthio group, a nitro group and an amino group which may have a C1-6 alkanoyl group as a substituent is substituted by 1 to 5 For example, phenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 2-bromophenyl Group, 3-bromophenyl group, 4-bromophenyl group, 2-iodophenyl group, 3-iodophenyl group Group, 4-iodophenyl group, 2,3-difluorophenyl group, 3,4-difluorophenyl group, 3,5-difluorophenyl group, 2,4-difluorophenyl group, 2,6-difluorophenyl group, 2 , 3-dichlorophenyl group, 3,4-dichlorophenyl group, 3,5-dichlorophenyl group, 2,4-dichlorophenyl group, 2,6-dichlorophenyl group, 3,4,5-trifluorophenyl group, 3,4,5 -Trichlorophenyl, 2,4,6-trifluorophenyl, 2,3,4,5,6-pentafluorophenyl, 2,4,6-trichlorophenyl, 2-methylphenyl, 3-methyl Phenyl, 4-methylphenyl, 2,4-dimethylphenyl, 2,4,6-trimethylphenyl, 2-methyl-3-chlorophenyl 3-methyl-4-chlorophenyl group, 2-chloro-4-methylphenyl group, 2-methyl-3-fluorophenyl group, 2-trifluoromethylphenyl group, 3-trifluoromethylphenyl group, 4-trifluoromethyl Phenyl, 2-pentafluoroethylphenyl, 3-pentafluoroethylphenyl, 4-pentafluoroethylphenyl, 2-isopropylphenyl, 3-isopropylphenyl, 4-isopropylphenyl, 2-tert-butyl Phenyl group, 3-tert-butylphenyl group, 4-tert-butylphenyl group, 2-sec-butylphenyl group, 3-sec-butylphenyl group, 4-sec-butylphenyl group, 2-n-heptafluoropropyl Phenyl group, 3-n-heptafluoropropylphenyl group , 4-n-heptafluoropropylphenyl group, 4-pentylphenyl group, 4-hexylphenyl group, 2-methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 2-methoxy-3-chlorophenyl group, 2-fluoro-3-methoxyphenyl group, 2-fluoro-4-methoxyphenyl group, 2,6-dimethoxyphenyl group, 2,4,6-trimethoxyphenyl group, 2,3,4-trifluorophenyl group, 3,4,5-trifluorophenyl group, 2-trifluoromethoxyphenyl group, 3-trifluoromethoxyphenyl group, 4-trifluoromethoxyphenyl group, 2-pentafluoroethoxyphenyl group, 3-pentafluoroethoxyphenyl group , 4-pentafluoroethoxyphenyl group, 2-isopropoxyphenyl group, -Isopropoxyphenyl group, 4-isopropoxyphenyl group, 2-tert-butoxyphenyl group, 3-tert-butoxyphenyl group, 4-tert-butoxyphenyl group, 2-sec-butoxyphenyl group, 3-sec-butoxy Phenyl group, 4-sec-butoxyphenyl group, 2-n-heptafluoropropoxyphenyl group, 3-n-heptafluoropropoxyphenyl group, 4-n-heptafluoropropoxyphenyl group, 4-pentoxyphenyl group, 4- Hexyloxyphenyl group, 2,3-methylenedioxyphenyl group, 3,4-methylenedioxyphenyl group, 3-nitrophenyl group, 2,3-dinitrophenyl group, 2,4,6-trinitrophenyl group, 4-nitrophenyl group, 3-methylthiophenyl group, 4-methylthione Group, 3-trifluoromethylthiophenyl group, 4-trifluoromethylthiophenyl group, 3-methanesulfonylphenyl group, 4-methanesulfonylphenyl group, 2-methanesulfonylphenyl group, 2-aminophenyl, 2,4-dia Phenyl groups such as miniphenyl, 2,4,6-triaminophenyl, 2-acetylaminophenyl group, 3-acetylaminophenyl group, 4-acetylaminophenyl group, etc. Unsubstituted C1-6 alkyl group, halogen substituted or unsubstituted C1-6 alkoxy group, C1-4 alkylenedioxy group, C1-6 alkylsulfonyl group, halogen substituted or unsubstituted C1-6 alkylthio group, nitro group And one or two C1 to 6 alkanoyl groups as a substituent One to five, preferably one to three, groups selected from the group consisting of amino groups may be substituted. When the substituent is a C1-4 alkylenedioxy group, it is preferable to substitute 1 to 3 substituents. Can be mentioned.

  Benzofuryl group [in the benzofuran ring, at least one of a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group is substituted For example, unsubstituted 2-benzofuryl group, 4-fluoro-2-benzofuryl group, 5-fluoro-2-benzofuryl group, 6-fluoro-2-benzofuryl group, 7-fluoro-2 -Benzofuryl group, 4-chloro-2-benzofuryl group, 5-chloro-2-benzofuryl group, 6-chloro-2-benzofuryl group, 7-chloro-2-benzofuryl group, 4-bromo-2-benzofuryl group, 5 -Bromo-2-benzofuryl, 6-bromo-2-benzofuryl, 7-bromo-2-benzofuryl, 4-methyl-2- Nzofryl group, 5-methyl-2-benzofuryl group, 6-methyl-2-benzofuryl group, 7-methyl-2-benzofuryl group, 4-trifluoromethyl-2-benzofuryl group, 5-trifluoromethyl-2-benzofuryl group Group, 6-trifluoromethyl-2-benzofuryl group, 7-trifluoromethyl-2-benzofuryl group, 4-ethyl-2-benzofuryl group, 5-ethyl-2-benzofuryl group, 6-ethyl-2-benzofuryl group 7-ethyl-2-benzofuryl group, 4-pentafluoroethyl-2-benzofuryl group, 5-pentafluoroethyl-2-benzofuryl group, 6-pentafluoroethyl-2-benzofuryl group, 7-pentafluoroethyl-2 -Benzofuryl group, 4-methoxy-2-benzofuryl group, 5-methoxy-2-benzofuryl group 6-methoxy-2-benzofuryl group, 7-methoxy-2-benzofuryl group, 4-trifluoromethoxy-2-benzofuryl group, 5-trifluoromethoxy-2-benzofuryl group, 6-trifluoromethoxy-2-benzofuryl group 7-trifluoromethoxy-2-benzofuryl, 4-isopropyl-2-benzofuryl, 5-isopropyl-2-benzofuryl, 6-isopropyl-2-benzofuryl, 7-isopropyl-2-benzofuryl, 4- Hexyl-2-benzofuryl group, 5-hexyl-2-benzofuryl group, 6-hexyl-2-benzofuryl group, 7-hexyl-2-benzofuryl group, 4-ethoxy-2-benzofuryl group, 5-ethoxy-2-benzofuryl group Group, 6-ethoxy-2-benzofuryl group, 7-ethoxy-2-benzo group Furyl group, 4-fluoro-5-trifluoromethyl-2-benzofuryl group, 6-fluoro-5-trifluoromethyl-2-benzofuryl group, 7-fluoro-5-trifluoromethyl-2-benzofuryl group, 4- Chloro-5-trifluoromethyl-2-benzofuryl group, 6-chloro-5-trifluoromethyl-2-benzofuryl group, 7-chloro-5-trifluoromethyl-2-benzofuryl group, 4-chloro-5-triol Fluoromethoxy-2-benzofuryl group, 6-chloro-5-trifluoromethoxy-2-benzofuryl group, 7-chloro-5-trifluoromethoxy-2-benzofuryl group, 3-benzofuryl group, 4-fluoro-3-benzofuryl group Group, 5-fluoro-3-benzofuryl group, 6-fluoro-3-benzofuryl group, 7-fluoro-3- Nzofuryl group, 4-chloro-3-benzofuryl group, 5-chloro-3-benzofuryl group, 6-chloro-3-benzofuryl group, 7-chloro-3-benzofuryl group, 4-bromo-3-benzofuryl group, 5- Bromo-3-benzofuryl group, 6-bromo-3-benzofuryl group, 7-bromo-3-benzofuryl group, 4-methyl-3-benzofuryl group, 5-methyl-3-benzofuryl group, 6-methyl-3-benzofuryl group Group, 7-methyl-3-benzofuryl group, 4-trifluoromethyl-3-benzofuryl group, 5-trifluoromethyl-3-benzofuryl group, 6-trifluoromethyl-3-benzofuryl group, 7-trifluoromethyl- 3-benzofuryl group, 4-ethyl-3-benzofuryl group, 5-ethyl-3-benzofuryl group, 6-ethyl-3-benzofuryl group Group, 7-ethyl-3-benzofuryl group, 4-pentafluoroethyl-3-benzofuryl group, 5-pentafluoroethyl-3-benzofuryl group, 6-pentafluoroethyl-3-benzofuryl group, 7-pentafluoroethyl- 3-benzofuryl group, 4-methoxy-3-benzofuryl group, 5-methoxy-3-benzofuryl group, 6-methoxy-3-benzofuryl group, 7-methoxy-3-benzofuryl group, 4-trifluoromethoxy-3-benzofuryl group , 5-trifluoromethoxy-3-benzofuryl, 6-trifluoromethoxy-3-benzofuryl, 7-trifluoromethoxy-3-benzofuryl, 4-isopropyl-3-benzofuryl, 5-isopropyl-3- Benzofuryl group, 6-isopropyl-3-benzofuryl group, 7-isopropanol Pill-3-benzofuryl group, 4-hexyl-3-benzofuryl group, 5-hexyl-3-benzofuryl group, 6-hexyl-3-benzofuryl group, 7-hexyl-3-benzofuryl group, 4-ethoxy-3-benzofuryl group Group, 5-ethoxy-3-benzofuryl group, 6-ethoxy-3-benzofuryl group, 7-ethoxy-3-benzofuryl group, 4-fluoro-5-trifluoromethyl-3-benzofuryl group, 6-fluoro-5-benzofuryl group Trifluoromethyl-3-benzofuryl group, 7-fluoro-5-trifluoromethyl-3-benzofuryl group, 4-chloro-5-trifluoromethyl-3-benzofuryl group, 6-chloro-5-trifluoromethyl-3 group -Benzofuryl group, 7-chloro-5-trifluoromethyl-3-benzofuryl group, 4-chloro-5-trifluoro group Methoxy-3-benzofuryl group, 6-chloro-5-trifluoromethoxy-3-benzofuryl group, 6,7-dichloro-5-trifluoromethoxy-3-benzofuryl group, 5,6,7-trichloro-2-benzofuryl group Group, a benzofuryl group such as 7-chloro-5-trifluoromethoxy-3-benzofuryl group [a halogen atom on a benzofuran ring, a halogen substituted or unsubstituted C1-6 alkyl and a halogen substituted or unsubstituted C1-6 alkoxy group And the group selected from the group consisting of may be substituted with 1 to 3 groups].

  Furyl group [on the furan ring, a phenyl group which may have a halogen atom as a substituent may be substituted. ] As a 2-furyl group, a 3, 5- diphenyl- 2-furyl group, 2, 4, 5- triphenyl 3- furyl group, 5- (4-chlorophenyl) 2-furyl group, for example, 4 -(4-fluorophenyl) -2-furyl group, 4- (2,3,4,5,6-pentafluorophenyl) -2-furyl group, 3- (4-bromophenyl) -2-furyl group, 3-furyl group, 5- (2,4-dichlorophenyl) -3-furyl group, 4- (2,4,6-trichlorophenyl) -3-furyl group, 3- (4-iodophenyl) -3-furyl group Furyl group such as group [1 to 3 phenyl groups which may have 1 to 5 halogen atoms as a substituent may be substituted on the furan ring. Can be mentioned.

Phenyl group (a halogen atom on a phenyl ring; halogen substituted or unsubstituted C1-6 alkyl group; C3-8 cycloalkyl group; hydroxyl group; halogen substituted or unsubstituted C1-8 alkoxy group; C3 C.sub.1-4 cycloalkoxy group; C.sub.1-4 alkylenedioxy group; cyano group; nitro group; phenyl C.sub.2-6 alkenyl group; C.sub.2-6 alkanoyloxy group; amino group sometimes having C.sub.1-6 alkanoyl group as a substituent;ア ル キ ル 6 alkylsulfonylamino group; phenyl C1-6 alkoxy group; phenoxy group; amino group substituted with at least one C1-6 alkyl group; amino group substituted with at least one phenyl group; amino C1-6 alkoxy group [amino And at least one C1-6 alkyl group may be substituted on the group]; C C1-6 alkoxycarbonyl group; C1-6 alkoxycarbonyl C1-6 alkoxy group; C1-6 alkylthio group; pyrrolyl group; imidazolyl group; piperidyl group; morpholino group; pyrrolidinyl group; thienyl group; benzofuryl group; piperazinyl group [on piperazine ring And at least one group selected from the group consisting of a benzoyl group which may have at least one of a C1-6 alkyl group, a phenyl C1-6 alkyl group and a C1-6 alkyl group as a substituent A quinolyl group [optionally substituted at least one of a group selected from the group consisting of a C1-6 alkoxy group and an oxo group on a quinoline ring]; a carbostyryl group substituted on a piperidine ring Of a group selected from the group consisting of optionally substituted piperidyl carbonyl group and triazolyl group At least one group may be substituted), for example, a phenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4- Chlorophenyl group, 2-bromophenyl group, 3-bromophenyl group, 4-bromophenyl group, 2-iodophenyl group, 3-iodophenyl group, 4-iodophenyl group, 2,3-difluorophenyl group, 3,4 -Difluorophenyl group, 3,5-difluorophenyl group, 2,4-difluorophenyl group, 2,6-difluorophenyl group, 2,3-dichlorophenyl group, 3,4-dichlorophenyl group, 3,5-dichlorophenyl group, 2,4-dichlorophenyl group, 2,6-dichlorophenyl group, 2,3,4-trifluorophenyl group, 3,4 3,5-trifluorophenyl group, 3,4,5-trichlorophenyl group, 2,4,6-trifluorophenyl group, 2,3,4,5,6-pentafluorophenyl group, 2,4,6- Trichlorophenyl group, 2-fluoro-4-chlorophenyl group, 2-fluoro-4-bromophenyl group, 3-fluoro-4-chlorophenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 2,6-Dimethylphenyl, 2,4,6-trimethylphenyl, 2-methyl-3-chlorophenyl, 3-methyl-4-chlorophenyl, 2-chloro-4-methylphenyl, 2-methyl- 3-fluorophenyl group, 2-trifluoromethylphenyl group, 3-trifluoromethylphenyl group, 4-trifluoromethylphenyl group, 3,5-diphenyl Trifluoromethyl) phenyl group, 3,4-di (trifluoromethyl) phenyl group, 2,4-di (trifluoromethyl) phenyl group, 2-pentafluoroethylphenyl group, 3-pentafluoroethylphenyl group, 4 -Pentafluoroethylphenyl group, 2-isopropylphenyl group, 3-isopropylphenyl group, 4-isopropylphenyl group, 2-tert-butylphenyl group, 3-tert-butylphenyl group, 4-tert-butylphenyl group, 2 -Sec-butylphenyl group, 3-sec-butylphenyl group, 4-sec-butylphenyl group, 4-n-butylphenyl group, 4-n-pentylphenyl group, 4-n-hexylphenyl group, 2-n -Heptafluoropropylphenyl group, 3-n-heptafluoropropylphenyl group, -N-heptafluoropropylphenyl group, 4-pentylphenyl group, 4-hexylphenyl group, 2-methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 2-methoxy-3-chlorophenyl group, 2- Fluoro-3-methoxyphenyl group, 2-fluoro-4-methoxyphenyl group, 4-cyclopropylphenyl group, 4-cyclobutylphenyl group, 4-cyclopentylphenyl group, 4-cyclohexylphenyl group, 4-cycloheptylphenyl group , 4-cyclooctylphenyl group, 2,6-dimethoxyphenyl group, 2-trifluoromethoxyphenyl group, 3-trifluoromethoxyphenyl group, 4-trifluoromethoxyphenyl group, 2,3-di (trifluoromethoxy) group Phenyl group, 3,5-di (trifluoromethoxy) ) Phenyl group, 2,4-di (trifluoromethoxy) phenyl group, 2-pentafluoroethoxyphenyl group, 3-pentafluoroethoxyphenyl group, 4-pentafluoroethoxyphenyl group, 2-isopropoxyphenyl group, 3- Isopropoxyphenyl group, 4-isopropoxyphenyl group, 2-tert-butoxyphenyl group, 3-tert-butoxyphenyl group, 4-tert-butoxyphenyl group, 2-sec-butoxyphenyl group, 3-sec-butoxyphenyl group Group, 4-sec-butoxyphenyl group, 4-n-hexyloxyphenyl group, 4-n-heptyloxyphenyl group, 4-n-octyloxyphenyl group, 2-n-heptafluoropropoxyphenyl group, 3-n -Heptafluoropropoxyphenyl group, 4-n-hepta Fluoropropoxyphenyl group, 4-cyclopropoxyphenyl group, 4-cyclobutoxyphenyl group, 4-cyclopentoxyphenyl group, 4-cyclohexyloxyphenyl group, 4-cycloheptyloxyphenyl group, 4-cyclooctyloxyphenyl group , 4-pentoxyphenyl group, 4-hexyloxyphenyl group, 2-hydroxyphenyl group, 3-hydroxyphenyl group, 4-hydroxyphenyl group, 2,4-dihydroxyphenyl group, 2,4,6-trihydroxyphenyl group Group, 2-methoxy-3-chlorophenyl group, 2-fluoro-3-hydroxyphenyl group, 2-fluoro-4-hydroxyphenyl group, 2,3-methylenedioxyphenyl group, 3,4-methylenedioxyphenyl group , 2,3-ethylenedioxyphenyl group, 3,4 Ethylenedioxyphenyl group, 2-cyanophenyl group, 3-cyanophenyl group, 4-cyanophenyl group, 2,3-dicyanophenyl group, 2,4,6-tricyanophenyl group, 2-nitrophenyl group, 3 -Nitrophenyl group, 4-nitrophenyl group, 2,4-dinitrophenyl group, 2,4,6-trinitrophenyl group, 2-cinnamylphenyl group, 3-cinnamylphenyl group, 4-cinnamylphenyl group , 2-acetyloxyphenyl group, 3-acetyloxyphenyl group, 2-aminophenyl group, 2,4-diaminophenyl group, 2,4,6-triaminophenyl group, 4-acetyloxyphenyl group, 2-propionyl Oxyphenyl group, 3-propionyloxyphenyl group, 4-propionyloxyphenyl group, 2-butyryloxyphenyl group , 3-butyryloxyphenyl group, 4-butyryloxyphenyl group, 4-pentanoyloxyphenyl group, 4-hexanoyloxyphenyl group, 2-acetylaminophenyl group, 3-acetylaminophenyl group, 4-acetyl Aminophenyl group, 2-propionylaminophenyl group, 3-propionylaminophenyl group, 4-propionylaminophenyl group, 2-butyrylaminophenyl group, 3-butyrylaminophenyl group, 4-butyrylaminophenyl group, 4 -Pentanoylaminophenyl group, 4-hexanoylaminophenyl group, 2-methanesulfonylaminophenyl group, 3-methanesulfonylaminophenyl group, 4-methanesulfonylaminophenyl group, 2-benzyloxyphenyl group, 3-benzyloxy Phenyl group, 4-benzyl Xyphenyl group, 2- (2-phenylethoxy) phenyl group, 3- (2-phenylethoxy) phenyl group, 4- (2-phenylethoxy) phenyl group, 2- (3-phenylpropoxy) phenyl group, 3- ( 3-phenylpropoxy) phenyl group, 4- (3-phenylpropoxy) phenyl group, 2- (4-phenylbutoxy) phenyl group, 3- (4-phenylbutoxy) phenyl group, 4- (4-phenylbutoxy) phenyl Group, 2- (5-phenylpentoxy) phenyl group, 3- (5-phenylpentoxy) phenyl group, 4- (5-phenylpentoxy) phenyl group, 2- (6-phenylhexyloxy) phenyl group, 3- (6-phenylhexyloxy) phenyl group, 4- (6-phenylhexyloxy) phenyl group, 2-phenoxyphen Group, 3-phenoxyphenyl group, 4-phenoxyphenyl group, 2-methylaminophenyl group, 3-ethylaminophenyl group, 4-propylaminophenyl group, 2-n-butylaminophenyl group, 3-n-pentyl Aminophenyl group, 4-n-hexycylaminophenyl group, 2-dimethylaminophenyl group, 3-dimethylaminophenyl group, 4-dimethylaminophenyl group, 2-diethylaminophenyl group, 3-diethylaminophenyl group, 4-diethylamino Phenyl group, 2-di- (n-propyl) aminophenyl group, 3-di- (n-propyl) aminophenyl group, 4-di- (n-propyl) aminophenyl group, 3-phenylaminophenyl group, 2 -Diphenylaminophenyl group, 3-diphenylaminophenyl group, 4-diphenylamino Phenyl group, 2- (2-methylaminoethoxy) phenyl group, 3-ethylaminomethoxyphenyl group, 2- (2-dimethylaminoethoxy) phenyl group, 3- (2-dimethylaminoethoxy) phenyl group, 4- ( 2-dimethylaminoethoxy) phenyl group, 2- (3-dimethylaminopropoxy) phenyl group, 3- (3-dimethylaminopropoxy) phenyl group, 4- (3-dimethylaminopropoxy) phenyl group, 4- (4-dimethylaminopropyl) phenyl group Dimethylamino butoxy) phenyl group, 4- (5-dimethylamino pentoxy) phenyl group, 4- (6-dimethylaminohexyloxy) phenyl group, 2- (2-diethylaminoethoxy) phenyl group, 3- (2-diethylamino) (Ethoxy) phenyl group, 4- (2-diethylaminoethoxy) phenyl group, 2- (3) Diethylaminopropoxy) phenyl group, 3- (3-diethylaminopropoxy) phenyl group, 4- (3-diethylaminopropoxy) phenyl group, 4- (4-diethylaminobutoxy) phenyl group, 4- (5-diethylaminopentoxy) phenyl group 4- (6-diethylaminohexyloxy) phenyl group, 2-methoxycarbonylphenyl group, 3-methoxycarbonylphenyl group, 4-methoxycarbonylphenyl group, 2-ethoxycarbonylphenyl group, 3-ethoxycarbonylphenyl group, 4- Ethoxycarbonylphenyl group, 4- (3-propoxycarbonyl) phenyl group, 4- (4-butoxycarbonyl) phenyl group, 4- (5-pentoxycarbonyl) phenyl group, 4- (6-hexyloxycarbonyl) phenyl group , 2 Methoxycarbonyl methoxyphenyl group, 3-methoxycarbonyl methoxyphenyl group, 4-methoxycarbonyl methoxyphenyl group, 2-ethoxycarbonyl methoxyphenyl group, 3-ethoxycarbonyl methoxyphenyl group, 4-ethoxycarbonyl methoxyphenyl group, 4- (3 -Propoxycarbonyl) methoxyphenyl group, 4- (4-butoxycarbonyl) methoxyphenyl group, 4- (5-pentoxycarbonyl) methoxyphenyl group, 4- (6-hexyloxycarbonyl) methoxyphenyl group, 4- (2 -Methoxycarbonylethoxy) phenyl group, 4- (2-ethoxycarbonyl) ethoxyphenyl group, 4- (2- (3-propoxycarbonyl) ethoxy) phenyl group, 4- (2- (4-butoxycarbonyl) ethoxy) phenyl Henyl group, 4- (2- (5-pentoxycarbonyl) ethoxy) phenyl group, 4- (2- (6-hexyloxycarbonyl) ethoxy) phenyl group, 4- (3-methoxycarbonylpropoxy) phenyl group, 4 -(3- (2-Ethoxycarbonyl) propoxy) pheny


And 4- (3- (3-propoxycarbonyl) propoxy) phenyl, 4- (3- (4-butoxycarbonyl) propoxy) phenyl, 4- (3- (5-pentoxycarbonyl) propoxy) phenyl Group, 4- (3- (6-hexyloxycarbonyl) propoxy) phenyl group, 4- (4-methoxycarbonylbutoxy) phenyl group, 4- (4- (2-ethoxycarbonyl) butoxy) phenyl group, 4- (4- (4- (2-ethoxycarbonyl) butoxy) phenyl group; 5-methoxycarbonylpentoxy) phenyl group, 4- (5- (2-ethoxycarbonyl) pentoxy) phenyl group, 4- (6- (2-ethoxycarbonyl) hexyloxy) phenyl group, 2-methylthiophenyl group, 3 -Methylthiophenyl group, 4-methylthiophenyl group, 4-ethylthiophenyl group, 4-n-propylthione , 4-isopropylthiophenyl group, 4-n-butylthiophenyl group, 4-tert-butylthiophenyl group, 4-n-pentylthiophenyl group, 4-n-hexylthiophenyl group, 2- (1 -Pyrrolyl) phenyl group, 3- (1-pyrrolyl) phenyl group, 4- (1-pyrrolyl) phenyl group, 2- (1-imidazolyl) phenyl group, 3- (1-imidazolyl) phenyl group, 4- (1 -Imidazolyl) phenyl group, 2- piperidino phenyl group, 3- piperidino phenyl group, 4- piperidino phenyl group, 4- morpholino phenyl group, 3- morpholino phenyl group, 2- morpholino phenyl group, 2- morpholino phenyl group (1-pyrrolidinyl) phenyl group, 3- (1-pyrrolidinyl) phenyl group, 4- (1-pyrrolidinyl) phenyl group, 2- (2-thienyl) pheny Group, 3- (2-thienyl) phenyl group, 4- (2-thienyl) phenyl group, 2- (2-benzofuryl) phenyl group, 3- (2-benzofuryl) phenyl group, 4- (2-benzofuryl) phenyl Group, 2- (1-piperazinyl) phenyl group, 3- (1-piperazinyl) phenyl group, 4- (1-piperazinyl) phenyl group, 2- (4-methyl-1-piperazinyl) phenyl group, 3- (4) -Methyl-1-piperazinyl) phenyl group, 4- (4-methyl-1-piperazinyl) phenyl group, 4- (4-ethyl-1-piperazinyl) phenyl group, 4- (4-n-propyl-1-piperazinyl) group ) Phenyl group, 4- (4-isopropyl-1-piperazinyl) phenyl group, 4- (4-n-butyl-1-piperazinyl) phenyl group, 4- (4-tert-butyl-1) -Piperazinyl) phenyl group, 4- (4-n-pentyl-1-piperazinyl) phenyl group, 4- (4-n-hexyl-1-piperazinyl) phenyl group, 4- (4-benzyl-1-piperazinyl) phenyl group Group, 4- (4- (2-phenethyl) -1-piperazinyl) phenyl group, 4- (4- (3-phenylpropyl) -1-piperazinyl) phenyl group, 4- (4- (4-phenylbutyl) phenyl group -1-piperazinyl) phenyl group, 4- (4- (5-phenylpentyl) -1-piperazinyl) phenyl group, 4- (4- (6-phenylhexyl) -1-piperazinyl) phenyl group, 4- (4 -Benzoyl-1-piperazinyl) phenyl group, 4- (4- (2-methylbenzoyl) -1-piperazinyl) phenyl group, 4- (4- (2,3-dimethylbenzoyl) group 1-piperazinyl) phenyl group, 4- (4- (2,4,6-trimethylbenzoyl) -1-piperazinyl) phenyl group, 4- (4- (3-methylbenzoyl) -1-piperazinyl) phenyl group, 4 -(4- (4-Methylbenzoyl) -1-piperazinyl) phenyl group, 4- (4- (4-ethylbenzoyl) -1-piperazinyl) phenyl group, 4- (4- (4-isopropylbenzoyl) -1 -Piperazinyl) phenyl group, 4- (4- (4-n-butylbenzoyl) -1-piperazinyl) phenyl group, 4- (4- (4-n-pentylbenzoyl) -1-piperazinyl) phenyl group, 4- (4- (4-n-hexylbenzoyl) -1-piperazinyl) phenyl group, 3- (2-quinolyl) phenyl, 4- (4,5,6-trimethoxy-3-quinoli) ) Phenyl group, 4- (6-methoxy-2-quinolyl) phenyl group, 2- (5,6-dimethoxy-4-quinolyl) phenyl group, 3- (2-oxo-3-quinolyl) phenyl group, 4- (2-oxo-3-quinolyl) phenyl group, 3- (5-methoxy-2-oxo-3-quinolyl) phenyl group, 4- (5-methoxy-2-oxo-3-quinolyl) phenyl group, 3- (6-methoxy-2-oxo-7-quinolyl) phenyl group, 4- (6-methoxy-2-oxo-3-quinolyl) phenyl group, 3- (7-methoxy-2-oxo-6-quinolyl) phenyl Group, 4- (7-methoxy-2-oxo-8-quinolyl) phenyl group, 3- (8-methoxy-2-oxo-3-quinolyl) phenyl group, 4- (8-methoxy-2-oxo-3) -Quinolyl) phenyl group, 3 -(5,6-diethoxy-2-oxo-4-quinolyl) phenyl group, 4- (5-ethoxy-2-oxo-3-quinolyl) phenyl group, 3- (6-ethoxy-2-oxo-5-yl group Quinolyl) phenyl, 4- (6-ethoxy-2-oxo-3-quinolyl) phenyl, 3- (7-ethoxy-2-oxo-3-quinolyl) phenyl, 4- (7-ethoxy-2-) Oxo-3-quinolyl) phenyl group, 3- (8-ethoxy-2-oxo-3-quinolyl) phenyl group, 4- (8-ethoxy-2-oxo-3-quinolyl) phenyl group, 3- (1- (1-) Phenyl groups such as piperidinylcarbonyl) phenyl, 4- (4- (carbostyryl-1-yl) piperidinyl-1-carbonyl) phenyl group, 4- (1,2,4-triazol-1-yl) phenyl group, etc. (Pheny On the ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group; a C3-8 cycloalkyl group; a hydroxyl group; a halogen substituted or unsubstituted C1-8 alkoxy group; a C3-8 cycloalkoxy group C1-4 alkylenedioxy group; cyano group; nitro group; phenyl C2-6 alkenyl group; C2-6 alkanoyloxy group; amino group sometimes having one or two C1-6 alkanoyl groups as a substituent; C1 6 6 alkylsulfonylamino group; phenyl C 1 to 6 alkoxy group; phenoxy group; amino group substituted by 1 to 2 C 1 to 6 alkyl group as a substituent; amino group substituted by 1 to 2 phenyl group; An amino C1-6 alkoxy group which may be substituted by 1 to 2 C1-6 alkyl group; C1-6 alkoxy carbony Group: C1-6 alkoxycarbonyl C1-6 alkoxy group; C1-6 alkylthio group; pyrrolyl group; imidazolyl group; piperidyl group; morpholino group; pyrrolidinyl group; thienyl group; benzofuryl group; piperazinyl group [substituted on piperazine ring At least one group selected from the group consisting of C1-6 alkyl group, phenyl C1-6 alkyl group and benzoyl group which may have 1 to 3 of C1-6 alkyl groups may be substituted A quinolyl group which may be substituted on at least one of a group selected from the group consisting of a C1-6 alkoxy group and an oxo group on a quinoline ring; a carbostyryl group may be substituted on a piperidine ring 1 to 5, preferably 1 to 3 groups selected from the group consisting of piperidyl carbonyl group and triazolyl group It may be done. When the substituent is a C1-4 alkylenedioxy group, it is preferable to substitute 1 to 3 substituents. Can be mentioned.

  Naphthyl group (at least one group selected from the group consisting of halogen atoms, halogen-substituted or unsubstituted C1-6 alkoxy groups, and amino groups optionally having a C1-6 alkyl group as a substituent, on a naphthalene ring As 4) may be, for example, 1-naphthylmethyl group, 2- (2-naphthyl) ethyl group, 1- (3-naphthyl) ethyl group, 3- (4-naphthyl) propyl group, 4 -(5-Naphthyl) butyl group, 5- (6-naphthyl) pentyl group, 6- (7-naphthyl) hexyl group, 2-methyl-3- (8-naphthyl) propyl group, 1,1-dimethyl-2 -(3-naphthyl) ethyl group, 2-fluoro-1-naphthyl group, 2-chloro-1-naphthyl group, 2-bromo-1-naphthyl group, 3-fluoro-1-naphthyl group, 3-chloro-1 -Naf Group, 3-bromo-1-naphthyl group, 4-fluoro-1-naphthyl group, 4-chloro-1-naphthyl group, 4-bromo-1-naphthyl group, 5-fluoro-1-naphthyl group, 5- Chloro-1-naphthyl group, 5-bromo-1-naphthyl group, 6-fluoro-1-naphthyl group, 6-chloro-1-naphthyl group, 6-bromo-1-naphthyl group, 7-fluoro-1-naphthyl group Group, 7-chloro-1-naphthyl group, 7-bromo-1-naphthyl group, 1-fluoro-2-naphthyl group, 8-fluoro-1-naphthyl group, 8-chloro-1-naphthyl group, 8-bromo -1-naphthyl group, 1-fluoro-2-naphthyl group, 1-chloro-2-naphthyl group, 1-bromo-2-naphthyl group, 3-fluoro-2-naphthyl group, 3-chloro-2-naphthyl group , 3-bromo-2-naphthyl group 4-fluoro-2-naphthyl group, 4-chloro-2-naphthyl group, 4-bromo-2-naphthyl group, 4-dimethylamino-1-naphthyl group, 2-methoxy-1-naphthyl group, 3-methoxy- 1-naphthyl group, 4-methoxy-1-naphthyl group, 5-methoxy-1-naphthyl group, 6-methoxy-1-naphthyl group, 7-methoxy-1-naphthyl group, 8-methoxy-1-naphthyl group, 2-trifluoromethoxy-1-naphthyl group, 3-trifluoromethoxy-1-naphthyl group, 4-trifluoromethoxy-1-naphthyl group, 5-trifluoromethoxy-1-naphthyl group, 6-trifluoromethoxy- 1-naphthyl group, 7-trifluoromethoxy-1-naphthyl group, 8-trifluoromethoxy-1-naphthyl group, 3-amino-2-naphthyl group, 2-methyl group Mino-1-naphthyl group, 4-ethylamino-2-naphthyl group, 5-propylamino-1-naphthyl group, 6-n-butylamino-2-naphthyl group, 7-n-pentylamino-1-naphthyl group 8-hexylamino-2-naphthyl group, 2,3-dichloro-1-naphthyl group, 2,4,6-trichloro-1-naphthyl group, 2-chloro-4-trifluoromethoxy-1-naphthyl group, 2-chloro-6-dimethylamino-1-naphthyl group, 2-dimethylamino-1-naphthyl group, 3-dimethylamino-1-naphthyl group, 4-dimethylamino-1-naphthyl group, 5-dimethylamino-1 group -Naphthyl group, 6-dimethylamino-1-naphthyl group, 7-dimethylamino-1-naphthyl group, 8-dimethylamino-1-naphthyl group, 1-methoxy-2-naphthyl group, 3 Methoxy-2-naphthyl group, 4-methoxy-2-naphthyl group, 5-methoxy-2-naphthyl group, 6-methoxy-2-naphthyl group, 7-methoxy-2-naphthyl group, 8-methoxy-2-naphthyl group Group, 1-trifluoromethoxy-2-naphthyl group, 3-trifluoromethoxy-2-naphthyl group, 4-trifluoromethoxy-2-naphthyl group, 5-trifluoromethoxy-2-naphthyl group, 6-trifluoro Methoxy-2-naphthyl group, 7-trifluoromethoxy-2-naphthyl group, 8-trifluoromethoxy-2-naphthyl group, 1-dimethylamino-2-naphthyl group, 3-dimethylamino-2-naphthyl group, 4 -Dimethylamino-2-naphthyl group, 5-dimethylamino-2-naphthyl group, 6-dimethylamino-2-naphthyl group, 7-dimethylamine A halogen atom, a halogen-substituted or unsubstituted C1-6 alkoxy group and a C1-6 alkyl group as a substituent on a naphthalene ring such as no-2-naphthyl group, 8-dimethylamino-2-naphthyl group Examples include a naphthyl group which may be substituted by 1 to 3 groups selected from the group of amino groups which may be possessed.

  (In the biphenylyl ring, at least one of a group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-9 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group is substituted. May be, for example, 3-biphenylyl group, 4-biphenylyl group, 2′-fluoro-3-biphenylyl group, 3′-fluoro-3-biphenylyl group, 4′-fluoro-3-biphenylyl group, 3 ', 4'-difluoro-3-biphenylyl group, 3', 4 ', 5'-trichloro-3-biphenylyl group, 2', 3 ', 4', 5 ', 6'-pentafluoro-4-biphenylyl Group, 2′-fluoro-3 ′, 4′-ditrifluoromethyl-3-biphenylyl group, 2 ′, 4′-difluoro-3-biphenylyl group, 3 ′, 5′-diphenyl group Luoro-3-biphenylyl group, 2′-chloro-3-biphenylyl group, 3′-chloro-3-biphenylyl group, 4′-chloro-3-biphenylyl group, 3 ′, 4′-dichloro-3-biphenylyl group, 2 ', 4'-dichloro-3-biphenylyl group, 3', 5'-dichloro-3-biphenylyl group, 2'-methyl-3-biphenylyl group, 3'-methyl-3-biphenylyl group, 4'-methyl -3-biphenylyl group, 3 ′, 4′-dimethyl-3-biphenylyl group, 2 ′, 4′-dimethyl-3-biphenylyl group, 3 ′, 5′-dimethyl-3-biphenylyl group, 2′-trifluoro Methyl-3-biphenylyl group, 3'-trifluoromethyl-3-biphenylyl group, 4'-trifluoromethyl-3-biphenylyl group, 3 ', 4'-ditrifluoromethyl-3-biphenyl Niryl group, 2 ′, 4′-ditrifluoromethyl-3-biphenylyl group, 3 ′, 5′-ditrifluoromethyl-3-biphenylyl group, 2′-methoxy-3-biphenylyl group, 3′-methoxy-3-3 Biphenylyl group, 4′-methoxy-3-biphenylyl group, 3 ′, 4′-dimethoxy-3-biphenylyl group, 2 ′, 4′-dimethoxy-3-biphenylyl group, 3 ′, 4 ′, 5′-trimethoxy- 3-biphenylyl group, 3 ', 5'-dimethoxy-3-biphenylyl group, 2'-trifluoromethoxy-3-biphenylyl group, 3'-trifluoromethoxy-3-biphenylyl group, 4'-trifluoromethoxy-3 -Biphenylyl group, 3 ', 4'- ditrifluoromethoxy-3- biphenylyl group, 2', 4'- ditrifluoromethoxy-3- biphenylyl group, 3 ', 5'-ditrifluoromethoxy-3-biphenylyl group, 2'-fluoro-4-biphenylyl group, 3'-fluoro-4-biphenylyl group, 4'-fluoro-4-biphenylyl group, 3', 4 ' -Difluoro-4-biphenylyl group, 2 ', 4'-difluoro-4-biphenylyl group, 3', 5'-difluoro-4-biphenylyl group, 2'-chloro-4-biphenylyl group, 3'-chloro-4 -Biphenylyl group, 4'-chloro-4-biphenylyl group, 3 ', 4'-dichloro-4-biphenylyl group, 2', 4'-dichloro-4-biphenylyl group, 3 ', 5'-dichloro-4- Biphenylyl group, 2′-methyl-4-biphenylyl group, 3′-methyl-4-biphenylyl group, 4′-methyl-4-biphenylyl group, 4′-ethyl-4-biphenylyl group, 4′- -Propyl-4-biphenylyl group, 4'-n-butyl-4-biphenylyl group, 4'-n-pentyl-4-biphenylyl group, 4'-n-hexyl-4-biphenylyl group, 4'-n-heptyl group -4-biphenylyl group, 4′-n-octyl-4-biphenylyl group, 4′-n-nonyl-4-biphenylyl group, 3 ′, 4′-dimethyl-4-biphenylyl group, 2 ′, 4′-dimethyl group -4-biphenylyl group, 3 ', 5'-dimethyl-4-biphenylyl group, 3', 4 ', 5'-trimethyl-4-biphenylyl group, 2'-trifluoromethyl-4-biphenylyl group, 3'- Trifluoromethyl-4-biphenylyl group, 4′-trifluoromethyl-4-biphenylyl group, 3 ′, 4′-ditrifluoromethyl-4-biphenylyl group, 2 ′, 4′-ditrifluoromethane Ru-4-biphenylyl group, 3 ', 5'-ditrifluoromethyl-4-biphenylyl group, 2'-methoxy-4-biphenylyl group, 3'-methoxy-4-biphenylyl group, 4'-methoxy-4-biphenylyl Group, 3 ', 4'-dimethoxy-4-biphenylyl group, 2', 4'-dimethoxy-4-biphenylyl group, 3 ', 4'-dimethoxy-2'-chloro-4-biphenylyl group, 3', 5 '-Dimethoxy-4-biphenylyl group, 2'-trifluoromethoxy-4-biphenylyl group, 3'-trifluoromethoxy-4-biphenylyl group, 4'-trifluoromethoxy-4-biphenylyl group, 3', 4 ' -Ditrifluoromethoxy-4-biphenylyl group, 2 ', 4'-ditrifluoromethoxy-4-biphenylyl group, 3', 5'-ditrifluoromethoxy (A group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-9 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group on the biphenylyl ring, such as -4-biphenylyl group 1 to 5 and preferably 1 to 3 may be substituted).

  A benzothienyl group (on the benzothiophene ring, at least one of a group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl and a halogen-substituted or unsubstituted C1-6 alkoxy group is substituted For example, 2-benzothienyl group, 3-benzothienyl group, 3-methyl-2-benzothienyl group, 2-methyl-3-benzothienyl group, 4-fluoro-2- Benzothienyl group, 5-fluoro-2-benzothienyl group, 4,5,6-trichloro-2-benzothienyl group, 6-fluoro-2-benzothienyl group, 7-fluoro-2-benzothienyl group, 4- Chloro-2-benzothienyl group, 5-chloro-2-benzothienyl group, 6-chloro-2-benzothienyl group, 7-chloro-2-benzothie Group, 4-bromo-2-benzothienyl group, 5-bromo-2-benzothienyl group, 6-bromo-2-benzothienyl group, 7-bromo-2-benzothienyl group, 5-methyl-2-benzo group Thienyl group, 6-methyl-2-benzothienyl group, 7-methyl-2-benzothienyl group, 4-trifluoromethyl-2-benzothienyl group, 5-trifluoromethyl-2-benzothienyl group, 6-triethyl group Fluoromethyl-2-benzothienyl group, 7-trifluoromethyl-2-benzothienyl group, 4-ethyl-2-benzothienyl group, 5-ethyl-2-benzothienyl group, 6-ethyl-2-benzothienyl group , 7-ethyl-2-benzothienyl group, 4-pentafluoroethyl-2-benzothienyl group, 5-pentafluoroethyl-2-benzothienyl group, 6- Intafluoroethyl-2-benzothienyl group, 7-pentafluoroethyl-2-benzothienyl group, 4-methoxy-2-benzothienyl group, 5-methoxy-2-benzothienyl group, 6-methoxy-2-benzothienyl group Group, 7-methoxy-2-benzothienyl group, 4-trifluoromethoxy-2-benzothienyl group, 5-trifluoromethoxy-2-benzothienyl group, 6-trifluoromethoxy-2-benzothienyl group, 7- Trifluoromethoxy-2-benzothienyl group, 4-fluoro-3-methyl-2-benzothienyl group, 5-fluoro-3-methyl-2-benzothienyl group, 6-fluoro-3-methyl-2-benzothienyl group Group, 7-fluoro-3-methyl-2-benzothienyl group, 4-chloro-3-methyl-2-benzothienyl group, 5 -Chloro-3-methyl-2-benzothienyl group, 6-chloro-3-methyl-2-benzothienyl group, 7-chloro-3-methyl-2-benzothienyl group, 4-bromo-3-methyl-2 -Benzothienyl group, 5-bromo-3-methyl-2-benzothienyl group, 6-bromo-3-methyl-2-benzothienyl group, 7-bromo-3-methyl-2-benzothienyl group, 5-methyl -3-Methyl-2-benzothienyl group, 6-methyl-3-methyl-2-benzothienyl group, 7-methyl-3-methyl-2-benzothienyl group, 3,4,6-trimethyl-2-benzo Thienyl group, 4,5,6-trimethoxy-2-benzothienyl group, 4-trifluoromethyl-3-methyl-2-benzothienyl group, 5-trifluoromethyl-3-methyl-2-benzothienyl group 6-trifluoromethyl-3-methyl-2-benzothienyl group, 7-trifluoromethyl-3-methyl-2-benzothienyl group, 4-ethyl-3-methyl-2-benzothienyl group, 5-ethyl- 3-methyl-2-benzothienyl group, 6-ethyl-3-methyl-2-benzothienyl group, 7-ethyl-3-methyl-2-benzothienyl group, 4-pentafluoroethyl-3-methyl-2- Benzothienyl group, 5-pentafluoroethyl-3-methyl-2-benzothienyl group, 6-pentafluoroethyl-3-methyl-2-benzothienyl group, 7-pentafluoroethyl-3-methyl-2-benzothienyl group Group, 4-methoxy-3-methyl-2-benzothienyl group, 5-methoxy-3-methyl-2-benzothienyl group, 6-methoxy-3-methyl-2 Benzothienyl group, 7-methoxy-3-methyl-2-benzothienyl group, 4-trifluoromethoxy-3-methyl-2-benzothienyl group, 5-trifluoromethoxy-3-methyl-2-benzothienyl group, 6-trifluoromethoxy-3-methyl-2-benzothienyl group, 7-trifluoromethoxy-3-methyl-2-benzothienyl group, 4-isopropyl-2-benzothienyl group, 5-isopropyl-3-methyl- 2-benzothienyl group, 6-isopropyl-2-benzothienyl group, 7-isopropyl-2-benzothienyl group, 4-hexyl-2-benzothienyl group, 5-hexyl-2-benzothienyl group, 6-hexyl- 2-benzothienyl group, 7-hexyl-2-benzothienyl group, 4-ethoxy-2-benzothienyl group, 5-eth Xy-2-benzothienyl group, 6-ethoxy-2-benzothienyl group, 7-ethoxy-2-benzothienyl group, 4-fluoro-5-trifluoromethyl-2-benzothienyl group, 6-fluoro-5- Trifluoromethyl-2-benzothienyl group, 7-fluoro-5-trifluoromethyl-2-benzothienyl group, 4-chloro-5-trifluoromethyl-2-benzothienyl group, 6-chloro-5-trifluoro Methyl-2-benzothienyl group, 7-chloro-5-trifluoromethyl-2-benzothienyl group, 4-chloro-5-trifluoromethoxy-2-benzothienyl group, 6-chloro-5-trifluoromethoxy- 2-benzothienyl group, 7-chloro-5-trifluoromethoxy-2-benzothienyl group, 4-fluoro-3-benzothienyl group , 5-fluoro-3-benzothienyl group, 6-fluoro-3-benzothienyl group, 7-fluoro-3-benzothienyl group, 4-chloro-3-benzothienyl group, 5-chloro-3-benzothienyl group , 6-chloro-3-benzothienyl group, 7-chloro-3-benzothienyl group, 4-bromo-3-benzothienyl group, 5-bromo-3-benzothienyl group, 6-bromo-3-benzothienyl group , 7-bromo-3-benzothienyl group, 4-fluoro-3-benzothienyl group, 5-methyl-3-benzothienyl group, 6-methyl-3-benzothienyl group, 7-methyl-3-benzothienyl group , 4-trifluoromethyl-3-benzothienyl group, 5-trifluoromethyl-3-benzothienyl group, 6-trifluoromethyl-3-benzothienyl group, 7-to Fluoromethyl-3-benzothienyl group, 4-fluoro-2-methyl-3-benzothienyl group, 5-fluoro-2-methyl-3-benzothienyl group, 6-fluoro-2-methyl-3-benzothienyl group 7-fluoro-2-methyl-3-benzothienyl group, 4-chloro-2-methyl-3-benzothienyl group, 5-chloro-2-methyl-3-benzothienyl group, 6-chloro-2-methyl group -3-benzothienyl group, 7-chloro-2-methyl-3-benzothienyl group, 4-bromo-2-methyl-3-benzothienyl group, 5-bromo-2-methyl-3-benzothienyl group, 6 -Bromo-2-methyl-3-benzothienyl group, 7-bromo-2-methyl-3-benzothienyl group, 4-fluoro-2-methyl-3-benzothienyl group, 5-methyl-2-methyone Le-3-benzothienyl group, 6-methyl-2-methyl-3-benzothienyl group, 7-methyl-2-methyl-3-benzothienyl group, 4-trifluoromethyl-2-methyl-3-benzothienyl group Group, 5-trifluoromethyl-2-methyl-3-benzothienyl group, 6-trifluoromethyl-2-methyl-3-benzothienyl group, 7-trifluoromethyl-2-methyl-3-benzothienyl group, 4-ethyl-3-benzothienyl group, 5-ethyl-3-benzothienyl group, 6-ethyl-3-benzothienyl group, 7-ethyl-3-benzothienyl group, 4-pentafluoroethyl-3-benzothienyl Group, 5-pentafluoroethyl-3-benzothienyl group, 6-pentafluoroethyl-3-benzothienyl group, 7-pentafluoroethyl-3-benzo group , 4-methoxy-3-benzothienyl group, 5-methoxy-3-benzothienyl group, 6-methoxy-3-benzothienyl group, 7-methoxy-3-benzothienyl group, 4-trifluoromethoxy-3 -Benzothienyl group, 5-trifluoromethoxy-3-benzothienyl group, 6-trifluoromethoxy-3-benzothienyl group, 7-trifluoromethoxy-3-benzothienyl group, 4-isopropyl-3-benzothienyl group , 5-isopropyl-3-benzothienyl group, 6-isopropyl-3-benzothienyl group, 7-isopropyl-3-benzothienyl group, 4-hexyl-3-benzothienyl group, 5-hexyl-3-benzothienyl group , 6-hexyl-3-benzothienyl group, 7-hexyl 3-benzothienyl group, 4-ethoxy- -Benzothienyl group, 5-ethoxy-3-benzothienyl group, 6-ethoxy-3-benzothienyl group, 7-ethoxy-3-benzothienyl group, 4-fluoro-5-trifluoromethyl-3-benzothienyl group , 6-fluoro-5-trifluoromethyl-3-benzothienyl group, 7-fluoro-5-trifluoromethyl-3-benzothienyl group, 4-chloro-5-trifluoromethyl-3-benzothienyl group, 6 -Chloro-5-trifluoromethyl-3-benzothienyl group, 7-chloro-5-trifluoromethyl-3-benzothienyl group, 4-chloro-5-trifluoromethoxy-3-benzothienyl group, 6-chloro -5-trifluoromethoxy-3-benzothienyl group, 7-chloro-5-trifluoromethoxy-3-benzothienyl group, etc. (In the benzothiophene ring, 1 to 3 groups selected from the group consisting of halogen atoms, halogen-substituted or unsubstituted C.sub.1-6 alkyl and halogen-substituted or unsubstituted C.sub.1-6 alkoxy groups are substituted. It may be Can be mentioned.

  A pyridyl group (a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group on a pyridine ring, a halogen atom, a halogen-substituted or an unsubstituted C1-6 alkyl group on a phenyl ring, and a halogen-substituted group Or at least one group selected from the group consisting of unsubstituted C1-6 alkoxy groups may be substituted], at least one group selected from the group consisting of furyl group and thienyl group For example, unsubstituted 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 3-fluoro-2-pyridyl group, 4-fluoro-2-pyridyl group, 5-fluoro- 2-pyridyl group, 6-fluoro-2-pyridyl group, 3-chloro-2-pyridyl group, 4-chloro-2-pyridyl group, 5-chloro-2-pyridyl group, 6-ku Ro-2-pyridyl group, 6-chloro-4-methyl-2-pyridyl group, 3,4,5-trichloro-2-pyridyl group, 3-methyl-2-pyridyl group, 4-methyl-2-pyridyl group , 5-methyl-2-pyridyl group, 6-methyl-2-pyridyl group, 3-ethyl-2-pyridyl group, 4-ethyl-2-pyridyl group, 5-ethyl-2-pyridyl group, 6-ethyl- 2-pyridyl group, 3-n-propyl-2-pyridyl group, 4-n-propyl-2-pyridyl group, 5-n-propyl-2-pyridyl group, 6-n-propyl-2-pyridyl group, 5 -Tert-butyl-2-pyridyl group, 4-n-pentyl-2-pyridyl group, 5-n-hexyl-2-pyridyl group, 6-n-hexyl-2-pyridyl group, 2-chloro-3-pyridyl group Group, 4-chloro-3-pyridyl group, 5-chloro 3-pyridyl group, 6-chloro-3-pyridyl group, 3-pyridyl group, 4-pyridyl group, 3-methyl-3-pyridyl group, 4-methyl-3-pyridyl group, 5-methyl-3-pyridyl group Group, 6-methyl-3-pyridyl group, 2-ethyl-3-pyridyl group, 4-ethyl-3-pyridyl group, 5-ethyl-3-pyridyl group, 6-ethyl-3-pyridyl group, 2-propyl -3-pyridyl group, 4-propyl-3-pyridyl group, 5-propyl-3-pyridyl group, 6-propyl-3-pyridyl group, 5-tert-butyl-3-pyridyl group, 4-pentyl-3- Pyridyl group, 5-hexyl-3-pyridyl group, 6-hexyl-3-pyridyl group, 3-chloro-4-pyridyl group, 2-chloro-4-pyridyl group, 3-methyl-4-pyridyl group, 2- Methyl-4-pyridyl group, 3- Trifluoromethyl-4-pyridyl group, 3-ethyl-4-pyridyl group, 2-ethyl-4-pyridyl group, 3-propyl-4-pyridyl group, 6-n-propyl-4-pyridyl group, 5-tert -Butyl-4-pyridyl group, 2-n-hexyl-4-pyridyl group, 3-phenyl-2-pyridyl group, 4-phenyl-2-pyridyl group, 5-phenyl-2-pyridyl group, 6-phenyl- 2-pyridyl group, 2-phenyl-3-pyridyl group, 2-phenyl-4-pyridyl group, 2-phenyl-5-pyridyl group, 3- (4-fluorophenyl) -2-pyridyl group, 3- (3) -Fluoro-4-chlorophenyl) -2-pyridyl group, 3- (3-fluorophenyl) -2-pyridyl group, 3- (4-bromophenyl) -4-pyridyl group, 3- (3-fluorophenyl)- 4- Lysyl group, 4- (2,3,4,5,6-pentafluorophenyl) -2-pyridyl group, 4- (3-fluoro-4-chlorophenyl) -2-pyridyl group, 4- (3-fluorophenyl) ) -2-pyridyl group, 3- (4-chlorophenyl) -2-pyridyl group, 4- (4-chlorophenyl) -2-pyridyl group, 5- (4-chlorophenyl) -2-pyridyl group, 6- (2) , 4,6-trichlorophenyl) -2-pyridyl group, 2- (4-chlorophenyl) -3-pyridyl group, 2- (4-chlorophenyl) -4-pyridyl group, 6- (4-chlorophenyl) -3- Pyridyl group, 4- (3-fluoro-4-chlorophenyl) -2-pyridyl group, 5- (4-iodo-3-chlorophenyl) -2-pyridyl group, 6- (4-fluoro-3-chlorophenyl) -2 - Zyl group, 2- (4-fluoro-3-chlorophenyl) -3-pyridyl group, 2- (4-fluoro-3-chlorophenyl) -4-pyridyl group, 6- (4-fluoro-3-chlorophenyl) -3 -Pyridyl group, 5- (4-trifluoromethylphenyl) -2-pyridyl group, 6- (4-trifluoromethylphenyl) -2-pyridyl group, 2- (4-trifluoromethylphenyl) -3-pyridyl group Group, 2- (4-trifluoromethylphenyl) -4-pyridyl group, 6- (4-trifluoromethylphenyl) -3-pyridyl group, 5- (4-methylphenyl) -2-pyridyl group, 6- (4-methylphenyl) -2-pyridyl group, 2- (4-methylphenyl) -3-pyridyl group, 2- (4-methylphenyl) -4-pyridyl group, 6- (4-methylphenyl)- 3-pyridyl group, 4-fluoro-2- (4-methoxyphenyl) -3-pyridyl group, 4-methyl-5-phenyl-3-chloro-2-pyridyl group, 5- (4-methoxyphenyl) -2 -Pyridyl group, 6- (4-methoxyphenyl) -2-pyridyl group, 2- (4-methoxyphenyl) -3-pyridyl group, 2- (4-methoxyphenyl) -4-pyridyl group, 6- (4) -Methoxyphenyl) -3-pyridyl group, 5- (4-trifluoromethoxyphenyl) -2-pyridyl group, 6- (4-trifluoromethoxyphenyl) -2-pyridyl group, 2- (4-trifluoromethoxy) Phenyl) -3-pyridyl group, 2- (4-trifluoromethoxyphenyl) -4-pyridyl group, 6- (4-trifluoromethoxyphenyl) -3-pyridyl group, 5- (3-chloro group 4-trifluoromethoxyphenyl) -2-pyridyl group, 6- (3-chloro-4-trifluoromethoxyphenyl) -2-pyridyl group, 2- (3-chloro-4-trifluoromethoxyphenyl) -3- Pyridyl group, 2- (3-chloro-4-trifluoromethoxyphenyl) -4-pyridyl group, 6- (3-chloro-4-trifluoromethoxyphenyl) -3-pyridyl group, 5- (3-fluoro- 4-trifluoromethoxyphenyl) -2-pyridyl group, 6- (3-fluoro-4-trifluoromethoxyphenyl) -2-pyridyl group, 2- (3-fluoro-4-trifluoromethoxyphenyl) -3- Pyridyl group, 2- (3-fluoro-4-trifluoromethoxyphenyl) -4-pyridyl group, 6- (3-fluoro-4-trifluoromethoxy) Phenyl) -3-pyridyl group, 5- (3,4-dimethoxyphenyl) -2-pyridyl group, 6- (3,4-dimethoxyphenyl) -2-pyridyl group, 2- (3,4-dimethoxyphenyl) 3-pyridyl group, 2- (3,4-dimethoxyphenyl) -4-pyridyl group, 6- (3,4-dimethoxyphenyl) -3-pyridyl group, 5- (3,4-difluorophenyl) -2 -Pyridyl group, 6- (3,4-difluorophenyl) -2-pyridyl group, 2- (3,4-difluorophenyl) -3-pyridyl group, 2- (3,4-difluorophenyl) -4-pyridyl group Group, 6- (3,4-difluorophenyl) -3-pyridyl group, 5- (3,4-dichlorophenyl) -2-pyridyl group, 6- (3,4-dichlorophenyl) -2-pyridyl group, 2- (3,4-dichloro) Rophenyl) -3-pyridyl group, 2- (3,4-dichlorophenyl) -4-pyridyl group, 6- (3,4-dichlorophenyl) -3-pyridyl group, 5- (2-furyl) -2-pyridyl group , 6- (2-furyl) -2-pyridyl group, 5- (2-furyl) -3-pyridyl group, 6- (2-furyl) -3-pyridyl group, 5- (3-furyl) -2- group Pyridyl group, 6- (3-furyl) -2-pyridyl group, 5- (3-furyl) -3-pyridyl group, 6- (3-furyl) -3-pyridyl group, 5- (2-thienyl)- 2-pyridyl group, 6- (2-thienyl) -2-pyridyl group, 5- (2-thienyl) -3-pyridyl group, 6- (2-thienyl) -3-pyridyl group, 5- (3-thienyl group ) -2-Pyridyl group, 6- (3-thienyl) -2-pyridyl group, 5- (3-thienyl) Pyridyl groups such as 3-pyridyl group, 6- (3-thienyl) -3-pyridyl group (a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group on a pyridine ring, a phenyl group [on a phenyl ring Is substituted by 1 to 5, preferably 1 to 3 groups selected from the group consisting of halogen atoms, halogen-substituted or unsubstituted C.sub.1-6 alkyl groups and halogen-substituted or unsubstituted C.sub.1-6 alkoxy groups; And the group selected from the group consisting of furyl group and thienyl group may be substituted with 1 to 3 groups.

  Furyl group (on the furan ring, a C1-6 alkyl group, a nitro group and a phenyl group [on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group, a halogen substituted or unsubstituted C1 At least one group selected from the group consisting of an alkoxy group of 6 to 6 and a nitro group may be substituted], and as the group selected from the group consisting of 1 to 3 may be substituted, For example, 2-furyl group, 3-furyl group, 3-methyl-2-furyl group, 3,4-dimethyl-2-furyl group, 3,4,5-trimethyl-2-furyl group, 4-methyl-2 -Furyl group, 5-methyl-2-furyl group, 3-ethyl-2-furyl group, 4-ethyl-2-furyl group, 5-ethyl-2-furyl group, 3-n-propyl-2-furyl group , 4-n-propyl-2-furyl group, 5- -Propyl-2-furyl group, 3-n-butyl-2-furyl group, 4-n-butyl-2-furyl group, 5-n-butyl-2-furyl group, 3-n-pentyl-2-furyl group Group, 4-n-pentyl-2-furyl group, 5-n-pentyl-2-furyl group, 3-n-hexyl-2-furyl group, 4-n-hexyl-2-furyl group, 5-n- Hexyl-2-furyl group, 2-methyl-3-furyl group, 4-methyl-3-furyl group, 5-methyl-3-furyl group, 2-ethyl-3-furyl group, 4-ethyl-3-furyl group Group, 5-ethyl-3-furyl group, 2-n-propyl-3-furyl group, 4-n-propyl-3-furyl group, 5-n-propyl-3-furyl group, 2-n-butyl- 3-furyl group, 4-n-butyl-3-furyl group, 5-n-butyl-3-furyl group, 2-n-pinch -3-furyl group, 4-n-pentyl-3-furyl group, 5-n-pentyl-3-furyl group, 2-n-hexyl-3-furyl group, 4-n-hexyl-3-furyl group, 5-n-hexyl-3-furyl group, 3-nitro-2-furyl group, 4-nitro-2-furyl group, 5-nitro-2-furyl group, 2-nitro-3-furyl group, 4-nitro -3-furyl group, 3-phenyl-2-furyl group, 4-phenyl-2-furyl group, 5-phenyl-2-furyl group, 3-phenyl-4-furyl group, 4-phenyl-3-furyl group , 3- (3-fluorophenyl) -2-furyl group, 4- (3-fluorophenyl) -2-furyl group, 5- (3-fluorophenyl) -2-furyl group, 2- (3-fluorophenyl) ) -3-furyl group, 3- (2-fluorophenyl) -2-furyl group, 4- (2-fluorophenyl) -2-furyl group, 5- (2-fluorophenyl) -2-furyl group, 2- (2-fluorophenyl) -3-furyl group, 4-nitro-3-furyl group 3- (4-fluorophenyl) -2-furyl group, 4- (4-fluorophenyl) -2-furyl group, 5- (4-fluorophenyl) -2-furyl group, 2- (4-fluorophenyl) ) 3-furyl group, 4- (4-fluorophenyl) -3-furyl group, 3- (3,4-difluorophenyl) -2-furyl group, 4- (2,3,4,5,6-) Pentafluorophenyl) -2-furyl group, 5- (3,4-difluorophenyl) -2-furyl group, 2- (3,4-difluorophenyl) -3-furyl group, 4- (3,4-difluoro) group Phenyl) -3-furyl group, 3- (4-chloropheny) ) -2-furyl group, 4- (4-chlorophenyl) -2-furyl group, 5- (4-chlorophenyl) -2-furyl group, 2- (4-chlorophenyl) -3-furyl group, 4- (4) -Chlorophenyl) -3-furyl group, 3- (2-chlorophenyl) -2-furyl group, 4- (2-chlorophenyl) -2-furyl group, 5- (2-chlorophenyl) -2-furyl group, 2- (2-chlorophenyl) -3-furyl group, 4- (2-chlorophenyl) -3-furyl group, 5- (2-chlorophenyl) -3-furyl group, 3- (3-chlorophenyl) -2-furyl group, 4- (3-chlorophenyl) -2-furyl group, 5- (3-chlorophenyl) -2-furyl group, 2- (3-chlorophenyl) -3-furyl group, 4- (3-chlorophenyl) -3-furyl Group, 3- (3, 4, 5) Trichlorophenyl) -2-furyl group, 4- (3,4-dichlorophenyl) -2-furyl group, 5- (3,4-dichlorophenyl) -2-furyl group, 2- (3,4-dichlorophenyl) -3 -Furyl group, 4- (3,4-dichlorophenyl) -3-furyl group, 3- (4-methylphenyl) -2-furyl group, 4- (4-methylphenyl) -2-furyl group, 5- (4- (4-methylphenyl) -2-furyl group) 4-methylphenyl) -2-furyl group, 2- (4-methylphenyl) -3-furyl group, 4- (4-methylphenyl) -3-furyl group, 3- (4-trifluoromethylphenyl)- 2-furyl group, 4- (4-trifluoromethylphenyl) -2-furyl group, 5- (4-trifluoromethylphenyl) -2-furyl group, 2- (4-trifluoromethylphenyl) -3- Furyl group, 4- (4-t Trifluoromethylphenyl) -3-furyl group, 3- (2-trifluoromethylphenyl) -2-furyl group, 4- (2-trifluoromethylphenyl) -2-furyl group, 5- (2-trifluoro) Methylphenyl) -2-furyl group, 2- (2-trifluoromethylphenyl) -3-furyl group, 4- (2-trifluoromethylphenyl) -3-furyl group, 3- (3-trifluoromethylphenyl) ) -2-Furyl group, 4- (3-trifluoromethylphenyl) -2-furyl group, 5- (4-trifluoromethylphenyl) -2-furyl group, 2- (3-trifluoromethylphenyl)- 3-furyl group, 4- (3-trifluoromethylphenyl) -3-furyl group, 3- (2-chloro-5-trifluoromethylphenyl) -2-furyl group, 4- (2-chloro-) -Trifluoromethylphenyl) -2-furyl group, 5- (2-chloro-5-trifluoromethylphenyl) -2-furyl group, 2- (2-chloro-5-trifluoromethylphenyl) -3-furyl group Group, 4- (2-chloro-5-trifluoromethylphenyl) -3-furyl group, 3- (4-methoxyphenyl) -2-furyl group, 4- (4-methoxyphenyl) -2-furyl group, 5- (4-methoxyphenyl) -2-furyl group, 3- (4-methoxyphenyl) -4-furyl group, 4- (4-methoxyphenyl) -3-furyl group, 3- (2-methoxyphenyl) -2-furyl group, 4- (2-methoxyphenyl) -2-furyl group, 5- (2-methoxyphenyl) -2-furyl group, 2- (2-methoxyphenyl) -3-furyl group, 4- (2-methoxypheny ) -3-Furyl group, 3- (2-trifluoromethoxyphenyl) -2-furyl group, 4- (2-trifluoromethoxyphenyl) -2-furyl group, 5- (2-trifluoromethoxyphenyl)- 2-furyl group, 3- (4-trifluoromethoxyphenyl) -2-furyl group, 4- (4-trifluoromethoxyphenyl) -2-furyl group, 5- (4-trifluoromethoxyphenyl) -2- group Furyl group, 2- (4-trifluoromethoxyphenyl) -3-furyl group, 4- (4-trifluoromethoxyphenyl) -3-furyl group, 3- (3,4-dimethoxyphenyl) -2-furyl group 4- (3,4-dimethoxyphenyl) -2-furyl group, 5- (3,4-dimethoxyphenyl) -2-furyl group, 3- (3,4-dimethoxyphenyl) -3-furyl group, 4- (3,4-dimethoxyphenyl) -3-furyl group, 3- (4-nitrophenyl) -2-furyl group, 4- (4-nitrophenyl) -2-furyl group, 5- (4-nitro) Phenyl) -2-furyl group, 2- (4-nitrophenyl) -3-furyl group, 4- (4-nitrophenyl) -3-furyl group, 3- (3-nitrophenyl) -2-furyl group, 4- (3-nitrophenyl) -2-furyl group, 5- (3-nitrophenyl) -2-furyl group, 2- (3-nitrophenyl) -3-furyl group, 4- (3-nitrophenyl) Furyl group such as -3-furyl group, 4-methyl-5-nitro-2-furyl group, 4-phenyl-3,5-dimethyl-2-furyl group (C1-6 alkyl group on furan ring , A nitro group and a phenyl group (on the phenyl ring, a halogen atom, a halogen Even if 1 to 5, preferably 1 to 3 groups selected from the group consisting of a substituted or unsubstituted C1-6 alkyl group, a halogen substituted or unsubstituted C1-6 alkoxy group and a nitro group are substituted 1 to 3 groups selected from the group consisting of (1) may be substituted.

  Examples of benzothiazole groups (on the benzothiazole ring, at least one phenyl group which may have a C1 to C6 alkoxy group on the phenyl ring as a substituent may be substituted) include, for example, benzothiazole groups -2-yl group, benzothiazol-4-yl group, benzothiazol-5-yl group, benzothiazol-6-yl group, benzothiazol-7-yl group, 2-phenylbenzothiazol-4-yl group, 2 5-diphenylbenzothiazol-4-yl group, 4,5,6-triphenylbenzothiazol-2-yl group, 2-phenylbenzothiazol-5-yl group, 2-phenylbenzothiazol-6-yl group, 2-phenylbenzothiazol-7-yl group, 2- (3-ethoxyphenyl) benzothiazol-7-yl group, 2- (4- Lpropoxyphenyl) benzothiazol-4-yl group, 2- (4-n-butoxyphenyl) benzothiazol-5-yl group, 2- (4-n-hexyloxyphenyl) benzothiazol-6-yl group, 2 -(4-n-Pentyloxyphenyl) benzothiazol-7-yl group, 4-phenylbenzothiazol-2-yl group, 5-phenylbenzothiazol-2-yl group, 6-phenylbenzothiazol-2-yl group 7-phenylbenzothiazol-2-yl group 4- (3,4-dimethoxyphenyl) benzothiazol-2-yl group 5- (3,4,5-trimethoxyphenyl) benzothiazol-2-yl group 7- (3-methoxyphenyl) benzothiazol-2-yl group, 4- (4-methoxyphenyl) benzothiazol-2-yl group, Benzothiazoles such as-(4-methoxyphenyl) benzothiazol-2-yl group, 6- (4-methoxyphenyl) benzothiazol-2-yl group, 7- (4-methoxyphenyl) benzothiazol-2-yl group Mentioning a group (on the benzothiazole ring, it may have 1 to 3 phenyl groups which may have 1 to 3 C1-6 alkoxy groups on the phenyl ring as substituents). it can.

  Thienyl group (a halogen atom, a nitro group, a C1-6 alkyl group on a thiophene ring, a pyrazolyl which may be substituted at least one halogen substituted or unsubstituted C1-6 alkyl group as a substituent on a pyrazole ring As the group and at least one group selected from the group consisting of a thienyl group optionally having a halogen atom on the thiophene ring may be substituted), for example, 2-thienyl group, 3-fluoro -2-thienyl group, 4-fluoro-2-thienyl group, 5-fluoro-2-thienyl group, 3-chloro-2-thienyl group, 4-chloro-2-thienyl group, 5-chloro-2-thienyl group , 3-bromo-2-thienyl group, 4-bromo-2-thienyl group, 5-bromo-2-thienyl group, 3-thienyl group, 2-fluoro-3-thienyl group, 4-fluo -3-thienyl group, 5-fluoro-3-thienyl group, 2-chloro-3-thienyl group, 4-chloro-3-thienyl group, 5-chloro-3-thienyl group, 2-bromo-3-thienyl group , 4-bromo-3-thienyl group, 5-bromo-3-thienyl group, 3-nitro-2-thienyl group, 4-nitro-2-thienyl group, 5-nitro-2-thienyl group, 2-nitro- 3-thienyl group, 4-nitro-3-thienyl group, 5-nitro-3-thienyl group, 3-methyl-2-thienyl group, 4-methyl-2-thienyl group, 5-methyl-2-thienyl group, 5-ethyl-2-thienyl group, 2-methyl-3-thienyl group, 4-methyl-3-thienyl group, 5-methyl-3-thienyl group, 2,5-dimethyl-3-thienyl group, 2,4 5-trimethyl-3-thienyl group, 2,4-di Tyl-3-thienyl group, 3- (pyrazol-yl) -2-thienyl group, 4- (pyrazol-1-yl) -2-thienyl group, 5- (pyrazol-1-yl) -2-thienyl group, 2- (pyrazol-1-yl) -3-thienyl group, 4- (pyrazol-1-yl) -3-thienyl group, 5- (pyrazol-1-yl) -3-thienyl group, 3- (3- (3-) Trifluoromethylpyrazole-yl) -2-thienyl group, 4- (3-trifluoromethylpyrazole-1-yl) -2-thienyl group, 5- (1-methyl-3-trifluoromethylpyrazole-5-yl) ) -2-thienyl group, 2- (1,4,5-trimethylpyrazol-3-yl) -3-thienyl group, 4- (1,5-dimethylpyrazol-3-yl) -3-thienyl group, 5 -(1-methyl-pyrazole- 3-yl) -3-thienyl group, 5- (1-n-pentyl-pyrazol-5-yl) -2-thienyl group, 5- (1-n-hexyl-pyrazol-5-yl) -2-thienyl Group, 3- (5-trifluoromethylpyrazol-yl) -2-thienyl group, 4- (5-n-propyl-pyrazol-1-yl) -2-thienyl group, 5- (5-n-butyl-) Pyrazol-1-yl) -2-thienyl group, 2- (5-trifluoromethylpyrazol-1-yl) -3-thienyl group, 4- (5-ethyl-pyrazol-1-yl) -3-thienyl group , 5- (5-trifluoromethylpyrazol-1-yl) -3-thienyl group, 3- (2-thienyl) -2-thienyl group, 4- (2-thienyl) -2-thienyl group, 3-chloro -4- (2-thienyl) -2-thienyl group, -(2-thienyl) -2-thienyl group, 2- (2-thienyl) -3-thienyl group, 4- (2-thienyl) -3-thienyl group, 5- (2-thienyl) -3-thienyl group 3- (5-chloro-2-thienyl) -2-thienyl group, 4- (5-bromo-2-thienyl) -2-thienyl group, 5- (5-chloro-2-thienyl) -2-thienyl group Group, 2- (5-chloro-2-thienyl) -3-thienyl group, 4- (5-chloro-2-thienyl) -3-thienyl group, 5- (5-chloro-2-thienyl) -3- Thienyl group, 3- (4-chloro-2-thienyl) -2-thienyl group, 4- (3,4-dichloro-2-thienyl) -2-thienyl group, 5- (3,4,5-trichloro- 2-thienyl) -2-thienyl group, 2- (4-bromo-2-thienyl) -3-thienyl Thienyl groups such as 4- (4-chloro-2-thienyl) -3-thienyl group, 5- (4-bromo-2-thienyl) -3-thienyl group, etc. (a halogen atom on a thiophene ring, a nitro group And C1-6 alkyl group, pyrazolyl group optionally substituted by 1 to 3 halogen-substituted or unsubstituted C1-6 alkyl groups as a substituent on the pyrazole ring, and 1 to 3 halogen atoms on the thiophene ring It may have 1 to 3 groups selected from the group consisting of optionally substituted thienyl groups. Can be mentioned.

  Indolyl group (group selected from the group consisting of phenylsulfonyl group which may have C1-6 alkyl group as a substituent, phenyl C1-6 alkyl group, C1-6 alkoxycarbonyl group and phenyl group on indole ring As at least one of the following may be substituted), for example: indol-1-yl, indol-2-yl, indol-3-yl, indol-4-yl, indol-5-yl, indole-6 -Yl, indole-7-yl, 1- (benzenesulfonyl) indol-3-yl group, 1- (4-methylbenzenesulfonyl) indol-3-yl group, 1- (3,4-dimethylbenzenesulfonyl) indole -3-yl group, 1- (3,4,6-trimethylbenzenesulfonyl) indol-3-yl group, 1-ben 1- (2-phenethyl) indol-3-yl group, 1- (1-phenethyl) indol-3-yl group, 1- (3-phenylpropyl) indol-3-yl group 1- (4-phenylbutyl) indol-3-yl group, 1- (5-phenylpentyl) indol-3-yl group, 1- (6-phenylhexyl) indol-3-yl group, 6-methoxycarbonyl Indol-3-yl group, 6-ethoxycarbonylindol-3-yl group, 6-n-propoxycarbonylindol-3-yl group, 6-n-butoxycarbonylindol-3-yl group, 6-n-pentyloxy Carbonylindol-3-yl group, 6-n-hexyloxycarbonylindol-3-yl group, 2-phenylindol-3-yl group 1-benzyl-6-phenyl-6-methoxycarbonylindol-3-yl group, 1-benzyl-6-methoxycarbonylindol-3-yl group, 2-phenyl-1- (4-methylbenzenesulfonyl) indole-3 Indolyl group (such as a phenylsulfonyl group which may have 1 to 3 C1-6 alkyl groups as a substituent, an phenyl C1-6 alkyl group, a C1-6 alkoxycarbonyl group and a phenyl group on the indole ring 1 to 3 groups selected from the group consisting of groups may be substituted.

  A pyrrolyl group (on the pyrrole ring, at least one group selected from the group consisting of a phenyl group which may be substituted by at least one halogen-substituted or unsubstituted C1-6 alkyl group and a C1-6 alkyl group; As 1) may be, for example, 2-pyrrolyl group, 1-methyl-2-pyrrolyl group, 1-ethyl-2-pyrrolyl group, 1-n-propyl-2-pyrrolyl group, 1-n -Butyl-2-pyrrolyl group, 1-n-pentyl-2-pyrrolyl group, 1-n-hexyl-2-pyrrolyl group, 3-pyrrolyl group, 1-methyl-3-pyrrolyl group, 1-ethyl-3-3 Pyrrolyl group, 1-n-propyl-3-pyrrolyl group, 1-n-butyl-3-pyrrolyl group, 1-n-pentyl-3-pyrrolyl group, 1-n-hexyl-3-pyrrolyl group, 2,5 -Dimethyl-3-pyrrolyl group 1- (3-methylphenyl) -2,5-dimethyl-3-pyrrolyl group, 1- (4-methylphenyl) -2,5-dimethyl-3-pyrrolyl group, 1- (3-trifluoromethylphenyl) -2,5-dimethyl-3-pyrrolyl group, 1- (4-trifluoromethylphenyl) -2,5-dimethyl-3-pyrrolyl group, 1- (2,3-dimethylphenyl) -3-pyrrolyl group, 1- (4-methylphenyl) -3-pyrrolyl group, 1- (3-trifluoromethylphenyl) -3-loryl group, 1- (4-trifluoromethylphenyl) -3-pyrrolyl group, 1- (3) -Methylphenyl) -3,5-dimethyl-2-pyrrolyl group, 1- (4-methylphenyl) -3,5-dimethyl-2-pyrrolyl group, 1- (3-trifluoromethylphenyl) -3,5 -Dimethyl-2-pi Ryl group, 1- (4-trifluoromethylphenyl) -3,5-dimethyl-2-pyrrolyl group, 1- (3-methylphenyl) -2-pyrrolyl group, 1- (2,4,6-trimethylphenyl) And pyrrolyl groups such as 1) (2-pyrrolyl group), 1- (3,5-ditrifluoromethylphenyl) -2-pyrrolyl group, 1- (4-trifluoromethylphenyl) -2-pyrrolyl group, etc. And a group selected from the group consisting of a phenyl group which may be substituted by 1 to 3 halogen-substituted or unsubstituted C1-6 alkyl groups and a C1-6 alkyl group may be substituted by 1 to 3) Can be mentioned.

  The coumaryl group includes 4-coumaryl group, 5-coumaryl group, 6-coumaryl group, 7-coumaryl group and 8-coumaryl group.

  Examples of the benzoimidazolyl group (on the benzimidazole ring, at least one thienyl group may be substituted) include, for example, 2-benzoimidazolyl group, 4-benzoimidazolyl group, 5-benzoimidazolyl group, 6-benzoimidazolyl group, 2 -(2-thienyl) -4-benzoimidazolyl group, 2- (2-thienyl) -5-benzoimidazolyl group, 2- (2-thienyl) -6-benzoimidazolyl group, 2- (2-thienyl) -7-benzoimidazolyl group , 2- (3-thienyl) -4-benzoimidazolyl group, 2- (3-thienyl) -5-benzoimidazolyl group, 2- (3-thienyl) -6-benzoimidazolyl group, 2- (3-thienyl) -7- Benzimidazolyl group etc. can be mentioned.

  Examples of the oxazolyl group (wherein at least one phenyl group which may have a halogen atom may be substituted on the oxazole ring) include, for example, 2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group, 2 -Phenyl-4-oxazolyl group, 2- (4-fluorophenyl) -4-oxazolyl group, 2,4-di (4-chlorophenyl) -5-oxazolyl group, 2- (4-chlorophenyl) -4-oxazolyl group , 2- (4-bromophenyl) -4-oxazolyl group, 2- (4-iodophenyl) -4-oxazolyl group, 2- (4-fluorophenyl) -5-oxazolyl group, 2- (4-chlorophenyl) -5-oxazolyl group, 2- (4-bromophenyl) -5-oxazolyl group, 2- (4-iodophenyl) -5-oxazolyl group 2- (4-fluorophenyl) -4-oxazolyl group, 2- (3,4-chlorophenyl) -4-oxazolyl group, 2- (4-bromophenyl) -5-oxazolyl group, 2- (4-iodophenyl) ) 5-oxazolyl group, 2- (2,3,4,5,6-pentafluorophenyl) -4-oxazolyl group, 2- (2,4,6-trichlorophenyl) -4-oxazolyl group, 2- Oxazolyl groups such as (4-bromophenyl) -5-oxazolyl group, 2- (4-iodophenyl) -5-oxazolyl group (a phenyl group which may have 1 to 5 halogen atoms on the oxazole ring) As a substituent, one to two may be substituted) can be mentioned.

  A thiazolyl group (at least one phenyl group may be substituted on the thiazole ring; at least one member selected from the group consisting of a halogen atom, a nitro group and a phenyl group on the phenyl ring May be substituted), for example, 2-thiazolyl group, 4-thiazolyl group, 5-thiazolyl group, 2-phenyl-4-thiazolyl group, 2-phenyl-5-thiazolyl group, 2,4 -Diphenyl-5-thiazolyl group, 2,5-diphenyl-4-thiazolyl group, 2- (4-chlorophenyl) -4-thiazolyl group, 2- (4-fluorophenyl) -5-thiazolyl group, 2- (2) , 3,4,5,6-pentafluorophenyl) -4-thiazolyl group, 2- (4-bromophenyl) -4-thiazolyl group, 2- (3,4-dichlorophenyl) -4-thia Ryl group, 2- (3,4-dichlorophenyl) -5-thiazolyl group, 2- (3,4-difluorophenyl) -5-thiazolyl group, 2- (2,4,6-trichlorophenyl) -4-thiazolyl Group, 2- (3-chloro-4-nitrophenyl) -4-thiazolyl group, 2- (4-phenyl-3-bromophenyl) -4-thiazolyl group, 2- (4-nitrophenyl) -4-thiazolyl group Group, 2- (4-nitrophenyl) -5-thiazolyl group, 2- (2,4,6-trinitrophenyl) -5-thiazolyl group, 2- (2,4-dinitrophenyl) -4-thiazolyl group 2- (4-biphenylyl) -4-thiazolyl group, 2- (4-biphenylyl) -5-thiazolyl group, 4- (4-biphenylyl) -2-thiazolyl group, 2- (4-biphenylyl) -4-thiazolyl group Thiazolyl And the like, or a thiazolyl group (for example, a group selected from the group consisting of a halogen atom, a nitro group and a phenyl group on the thiazole ring is 1 to 5, preferably 1 to 3 substituted phenyl groups may be substituted. 2 may be substituted.) Can be mentioned.

  The quinolyl group includes 2-quinolyl group, 3-quinolyl group, 4-quinolyl group, 5-quinolyl group, 6-quinolyl group, 7-quinolyl group and 8-quinolyl group.

  A 3,4-dihydrocarbostyryl group (on the 3,4-dihydrocarbostyryl ring, at least one of a group selected from the group consisting of a C.sub.1-6 alkoxy group, a C.sub.1-6 alkyl group and a phenyl C.sub.1-6 alkoxy group; And at least one of the groups selected from the group consisting of a C 1-6 alkoxy group, a C 1-6 alkyl group and a phenyl C 1-6 alkoxy group on the carbostyryl ring (which may be substituted with a species) As the species may be substituted), for example, 3,4-dihydrocarbostyryl-1-yl group, 3,4-dihydrocarbostyryl-3-yl group, 3,4-dihydrocarbostyryl-4- Group, 3,4-dihydrocarbostyryl-5-yl group, 3,4-dihydrocarbostyryl-6-yl group, 3,4-dihydrocarbostyryl-7-yl group 3,4-dihydrocarbostyryl-8-yl group, carbostyryl-1-yl group, carbostyryl-3-yl group, carbostyryl-4-yl group, carbostyryl-5-yl group, carbostyryl-6, -Yl, carbostyryl-7-yl, carbostyryl-8-yl, 6-methoxy-3,4-dihydrocarbostyryl-5-yl, 7-methoxy-3,4-dihydrocarbostyryl-5 -Yl group, 8-methoxy-3,4-dihydrocarbostyryl-5-yl group, 8-methoxy-1-methyl-3,4-dihydrocarbostyryl-5-yl group, 8-benzyloxy-3, 4 -Dihydrocarbostyryl-5-yl group, 8-methoxycarbostyryl-5-yl group, 8-methoxy-1-methylcarbostyryl-5-yl group, 8-benzyloxycar Styryl-5-yl group, 8-methoxy-3,4-dihydrocarbostyryl-6-yl group, 6-methyl-3,4-dihydrocarbostyryl-5-yl group, 6,7-dimethyl-3,4 -Dihydrocarbostyryl-5-yl group, 1,5,6-trimethyl-3,4-dihydrocarbostyryl-7-yl group, 6-methylcarbostyryl-5-yl group, 6,7-dimethylcarbostyryl- 5-yl, 1,5,6-trimethylcarbostyryl-7-yl, 8-methoxy-1-methyl-3,4-dihydrocarbostyryl-6-yl, 8-benzyloxy-3,4- Dihydrocarbostyryl-6-yl group, 8-methoxycarbostyryl-6-yl group, 8-methoxy-1-methylcarbostyryl-6-yl group, 8-benzyloxycarbostyryl-6-yl group Group, 8-methoxy-3,4-dihydrocarbostyryl-7-yl group, 8-methoxy-1-methyl-3,4-dihydrocarbostyryl-7-yl group, 8-benzyloxy-3,4-dihydro group Carbostyryl-7-yl group, 8-ethoxycarbostyryl-7-yl group, 8-methoxy-1-propylcarbostyryl-7-yl group, 8- (2-phenylethoxy) carbostyryl-7-yl group, etc. (In the 3,4-dihydrocarbostyryl ring, a group selected from the group consisting of a C1-6 alkoxy group, a C1-6 alkyl group and a phenyl C1-6 alkoxy group is And -3 substituted carbostyryl groups (on the carbostyryl ring, C1-6 alkoxy, C1-6 alkyl and phenyl C1-6 alkoxy) Ranaru group selected from the group may also be one to three substituents. Can be mentioned.

  Examples of the imidazo [2,1-b] thiazolyl group include 6-imidazo [2,1-b] thiazolyl group, 5-imidazo [2,1-b] thiazolyl group, 3-imidazo [2,1-b] Thiazolyl group, 2-imidazo [2,1-b] thiazolyl group, etc. can be mentioned.

  As the imidazo [2,1-a] pyridyl group, for example, 2-imidazo [2,1-a] pyridyl group, 3-imidazo [2,1-a] pyridyl group, 5-imidazo [2,1-a] pyridyl group ] A pyridyl group, 6- imidazo [2, 1-a] pyridyl group, 7- imidazo [2, 1-a] pyridyl group etc. can be mentioned.

  As the chromanyl group (on the chroman ring, at least one C1-6 alkyl group may be substituted), for example, 2-methyl-5-chromanyl group, 2,2-dimethyl-5-chromanyl group , 2-methyl-6-chromanyl group, 2-ethyl-6-chromanyl group, 2-n-propyl-6-chromanyl group, 2-n-butyl-6-chromanyl group, 2-n-pentyl-6-chromanyl Group, 2-n-hexyl-6-chromanyl group, 2,2-dimethyl-6-chromanyl group, 2,2-diethyl-6-chromanyl group, 2-methyl-7-chromanyl group, 2,2-dimethyl- Chromanyl groups such as 7-chromanyl group, 2,2,4-trimethyl-6-chromanyl group, 2-methyl-8-chromanyl group, 2,2-dimethyl-8-chromanyl group (C1-6 on chroman ring Archi Group can be mentioned may) also be 1-3 substituents.

  As the 2,3-dihydrobenzofuryl group, for example, 2,3-dihydro-4-benzofuryl group, 2,3-dihydro-5-benzofuryl group, 2,3-dihydro-6-benzofuryl group, 2,3-dihydrobenzofuryl group A dihydro-7-benzofuryl group etc. can be mentioned.

  Amino-substituted C.sub.1-6 alkyl group [wherein the phenyl group (the phenyl ring has a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group on the phenyl group. As at least one group selected from the group consisting of at least one group selected from the group and at least one group selected from the group consisting of a C1-6 alkyl group], for example, an amimethyl group , 2-aminoethyl group, 1-aminoethyl group, 3-aminopropyl group, 4-aminobutyl group, 5-aminopentyl group, 6-aminohexyl group, 2-methyl-3-aminopropyl group, 1, 1 -Dimethyl-2-aminoethyl group, 2- (methylamino) ethyl group, 3- (methylamino) propyl group, 4- (methylamino) butyl group, 5- (methylamino) group ) Pentyl group, 6- (methylamino) hexyl group, dimethylaminomethyl group, 2- (diethylamino) ethyl group, 3- (di n-propylamino) propyl group, 4- (di n-butylamino) butyl group, 5- (di n-pentylamino) pentyl group, 2- (di n-hexylamino) hexyl group, anilinomethyl group, 2- (N-methyl anilino) ethyl group, 3- (N- methyl anilino) propyl group, 4- anilino butyl Group, 2- (N-methyl-4-chloroanilino) ethyl group, 3- (N-methyl-4-chloroanilino) propyl group, 4- (N-methyl-4-chloroanilino) butyl group, 2- (N-methyl group -4-fluoroanilino) ethyl group, 3- (N-methyl-2,3,4,5,6-pentafluoroanilino) propyl group, 2- (3-fluoro-arene) Lino) ethyl group, 3- (N-methyl-3-fluoroanilino) propyl group, 4- (3-fluoro-anilino) butyl group, 2- (N-methyl-2-fluoro-anilino) ethyl group, 3 -(2-fluoroanilino) propyl, 4- (N-methyl-2-fluoroanilino) butyl, 2- (N-methyl-2-chloroanilino) ethyl, 3- (N-methyl-2-) Chloroanilino) propyl group, 4- (N-methyl-2-chloroanilino) butyl group, 2- (N-methyl-2,3-dichloroanilino) ethyl group, 3- (N-methyl-2,4,6- Trichloroanilino) propyl group, 4- (N-methyl-3-chloroanilino) butyl group, 2- (N-methyl-4-trifluoromethyl-anilino) ethyl group, 2- (4-methylanilino) ethyl group, 2 -(N -Ethyl-3,5-ditrifluoromethyl-anilino) ethyl group, 2- (N-methyl-3,5-ditrifluoromethylanilino) ethyl group, 2- (N-methyl-2,4-dimethylanilino) ) Ethyl group, 2- (N-methyl-3,5-dimethoxyanilino) ethyl group, 2- (2,4,6-trimethylanilino) ethyl group, 2- (3,4,5-trimethoxy ani group Lino) ethyl group, 3- (N-methyl-4-trifluoromethylanilino) propyl group, 4- (N-methyl-4-trifluoromethylanilino) butyl group, 2- (N-methyl-3-) Trifluoromethylanilino) ethyl, 3- (N-methyl-3-trifluoromethylanilino) propyl, 2- (N-methyl-2-trifluoromethylanilino) ethyl, 3- (N- Methyl-2-trif Omethylanilino) propyl, 4- (N-methyl-2-trifluoromethylanilino) butyl, 2- (N-methyl-4-trifluoromethoxyanilino) ethyl, 3- (N-methyl -4-Trifluoromethoxyanilino) propyl, 4- (4-trifluoromethoxyanilino) butyl, 2- (N-methyl-3-trifluoromethoxyanilino) ethyl, 3- (N-methyl -3-trifluoromethoxyanilino) propyl group, 4- (N-methyl-3-trifluoromethoxyanilino) butyl group, 2- (N-methyl-2-trifluoromethoxyanilino) ethyl group, 3- (N-methyl-2-trifluoromethoxyanilino) propyl group, 4- (N-methyl-2-trifluoromethoxyamino) butyl group, 2- (N-methyl-4-amino) Toxianilino) ethyl group, 3- (N-methyl-4-methoxyanilino) propyl group, 4- (N-methyl-4-methoxyanilino) butyl group, 2- (N-methyl-3-methoxyanilino) Ethyl, 3- (N-methyl-3-methoxy-anilino) propyl, 4- (3-methoxyanilino) butyl, 2- (2-methoxyanilino) ethyl, 3- (N-methyl- As a substituent such as 2-methoxyanilino) propyl group, 4- (N-methyl-2-methoxyanilino) butyl group, etc. (a halogen atom, halogen-substituted or unsubstituted C1-6 alkyl on the phenyl ring One to five, preferably one to three, groups selected from the group consisting of a group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted. And C 1 -C 6 alkyl groups which may have one or two groups selected from the group consisting of C 1 -C 6 alkyl groups.

  As a 1,4-dioxaazaspiro [4,5] decyl group (at least one oxo group may be substituted on the 1,4-dioxaazaspiro [4,5] decane ring) Is, for example, 1,4-dioxa-8-azaspiro [4,5] dec-8-yl group, 7-oxo-1,4-dioxa-8-azaspiro [4,5] dec-8-yl group, Examples include 6-oxo-1,4-dioxa-8-azaspiro [4,5] dec-8-yl group and the like.

  In the homopiperazinyl group (in the homopiperazine ring, at least one of a group selected from the group consisting of a C.sub.1-6 alkoxycarbonyl group, a phenyl C.sub.1-6 alkoxycarbonyl group and a phenyl substituted or unsubstituted phenyl group is substituted. And 1-homopiperazinyl group, 2-homopiperazinyl group, 3-homopiperazinyl group, 4-homopiperazinyl group, 5-homopiperazinyl group, 6-homopiperazinyl group, 7-homopiperazinyl group, 4-methoxycarbonyl-1 group. Homopiperazinyl group, 4-ethoxycarbonyl-1-homopiperazinyl group, 4-n-propoxycarbonyl-1-homopiperazinyl group, 4-tert-butoxycarbonyl-1-homopiperazinyl group, 4-n-pentyl Oxycarbonyl-1-homopipe Zinnyl group, 4-n-hexyloxycarbonyl-1-homopiperazinyl group, 4-benzyloxycarbonyl-1-homopiperazinyl group, 4- (2-phenylethoxycarbonyl) -1-homopiperazinyl group, 4- (3-phenylpropoxycarbonyl) -1-homopiperazinyl group, 4- (4-phenylbutoxycarbonyl) -1-homopiperazinyl group, 4- (5-phenylpentyloxycarbonyl) -1-homopiperazinyl group, 4- (6-phenylhexyloxycarbonyl) -1-homopiperazinyl group, 4- (4-biphenylyl) -1-homopiperazinyl group, 3,4-diphenyl-1-homopiperazinyl group, 3,4,5-triphenyl -1-homopiperazinyl group, 3-phenyl-4-methoxycarbonyl-1-homopiy Homopiperazinyl groups such as a razinyl group (1 to 3 groups selected from the group consisting of C1-6 alkoxycarbonyl group, phenyl C1-6 alkoxycarbonyl group and phenyl substituted or unsubstituted phenyl group on the homopiperazine ring And may be substituted).

  Piperazinyl group (in the piperazine ring, oxo group, C1-6 alkyl group, phenyl C1-6 alkyl group [in phenyl ring, at least one of halogen substituted or unsubstituted C1-6 alkyl group is substituted As at least one group selected from the group consisting of [1] may be substituted], for example, piperazin-1-yl group, piperazin-2-yl group, piperazin-3-yl group, Piperazin-4-yl group, 1-methyl-piperazin-4-yl group, 1-benzyl-piperazin-4-yl group, 1,2-dimethyl-piperazin-4-yl group, 1-benzyl-2,6- Dimethyl-piperazin-4-yl group, 1-ethyl-2-oxopiperazin-4-yl group, 1-n-propyl-2-oxopiperazin-4-yl group, 1-isopropyl-2-o group Sopiperazin-4-yl group, 1-n-butyl-2-oxopiperazin-4-yl group, 1-tert-butyl-2-oxopiperazin-4-yl group, 1-n-pentyl-2-oxopiperazine- 4-yl group, 1-n-hexyl-2-oxopiperazin-4-yl group, 1- (4-benzyl) -2-oxopiperazin-4-yl group, 1- (2,4-dimethylbenzyl) piperazine -4-yl group, 1- (2,4,6-trimethylbenzyl) piperazin-4-yl group, 1- (3,5-ditrifluoromethylbenzyl) piperazin-4-yl group, 1- (4-methyl group) Benzyl) -2-oxopiperazin-4-yl group, 1- (4-trifluoromethylbenzyl) -2-oxopiperazin-4-yl group, 1- [2- (4-trifluoromethylphenyl) ethyl -2-oxopiperazin-4-yl group, 1- [3- (4-trifluoromethylphenyl) propyl] -2-oxopiperazin-4-yl group, 1- [4- (4-trifluoromethylphenyl) group Butyl] -2-oxopiperazin-4-yl group, 1- [5- (4-trifluoromethylphenyl) pentyl] -2-oxopiperazin-4-yl group, 1- [6- (4-trifluoromethyl) group Piperazinyl groups such as (phenyl) hexyl] -2-oxopiperazin-4-yl group (in the piperazine ring, oxo group, C.sub.1-6 alkyl group, phenyl C.sub.1-6 alkyl group [in the phenyl ring or halogen substituted or The group selected from the group consisting of 1 to 3 unsubstituted C1-6 alkyl groups may be substituted] may be substituted 1 to 3).

  Examples of the piperidyl group (on the piperidine ring, at least one oxo group may be substituted) include, for example, 1-piperidyl group, 2-piperidyl group, 3-piperidyl group, 4-piperidyl group, 2- Examples include oxo-1-piperidyl group, 3-oxo-1-piperidyl group, 4-oxo-1-piperidyl group and the like.

  As a pyrrolidinyl group (on the pyrrolidine ring, at least one phenoxy C1-6 alkyl group optionally having halogen-substituted or unsubstituted C1-6 alkoxy group as a substituent may be substituted), for example, Pyrrolidin-1-yl group, pyrrolidin-2-yl group, pyrrolidin-3-yl group, 2-phenoxymethylpyrrolidin-1-yl group, 3-phenoxymethylpyrrolidin-1-yl group, 2- (2,4- Dimethoxyphenoxymethyl) pyrrolidin-1-yl group, 2- (2,4,6-trimethoxyphenoxymethyl) pyrrolidin-1-yl group, 2,3-diphenoxymethylpyrrolidin-1-yl group, 1,3, 4-phenoxymethylpyrrolidin-2-yl group, 2- (4-methoxyphenoxymethyl) pyrrolidin-1-yl group, 2- (4- Trifluoromethoxyphenoxymethyl) pyrrolidin-1-yl group, 2- [2- (3-trifluoromethoxyphenoxy) ethyl] pyrrolidin-1-yl group, 2- [3- (4-trifluoromethoxyphenoxy) propyl] Pyrrolidin-1-yl group, 2- [4- (4-trifluoromethoxyphenoxy) butyl] pyrrolidin-1-yl group, 2- [5- (4-trifluoromethoxyphenoxy) pentyl] pyrrolidin-1-yl group , 2- [6- (4-trifluoromethoxyphenoxy) hexyl] pyrrolidin-1-yl group, 3- (4-methoxyphenoxymethyl) pyrrolidin-1-yl group, 3- (3-trifluoromethoxyphenoxymethyl) Pyrrolidin-1-yl group, 3- (4-trifluoromethoxyphenoxymethyl) pyrrolidin-1-yl (1 to 3 phenoxy C1-6 alkyl groups which may have 1 to 3 halogen-substituted or unsubstituted C1 to 6 alkoxy groups as substituents on the pyrrolidine ring) Can be mentioned.

  Examples of the isoindolinyl group include 2-isoindolinyl group, 1-isoindolinyl group, 3-isoindolinyl group, 4-isoindolinyl group, 5-isoindolinyl group, 6-isoindolinyl group and the like.

  Examples of the oxazolidinyl group (at least one oxo group may be substituted on the oxazolidine ring) include, for example, 2-oxazolidinyl group, 3-oxazolidinyl group, 4-oxazolidinyl group, 5-oxazolidinyl group, An oxo-3-oxazolidinyl group etc. can be mentioned.

  Even if at least one of a group selected from the group consisting of an oxo group, a halogen atom and a phenyl group as a substituent is substituted on a benzo-1,3-oxazolidinyl group (benzo-1,3-oxazolidine ring As preferable), for example, benzo-1,3-oxazolidin-2-yl group, benzo-1,3-oxazolidin-3-yl group, benzo-1,3-oxazolidin-4-yl group, benzo-1 ,. 3-oxazolidin-5-yl group, benzo-1,3-oxazolidin-6-yl group, benzo-1,3-oxazolidin-7-yl group, 2-oxobenzo-1,3-oxazolidin-3-yl group, 4-chloro-2-oxobenzo-1,3-oxazolidin-3-yl group, 5-chloro-2-oxobenzo-1,3-oxazolidin-3-yl group, 5-bromo- -Oxobenzo-1,3-oxazolidin-3-yl group, 5-fluoro-benzo-1,3-oxazolidin-3-yl group, 6-phenyl-benzo-1,3-oxazolidin-3-yl group, 5- Bromo-6-phenyl-2-oxobenzo-1,3-oxazolidin-3-yl group, 6-chloro-2-oxobenzo-1,3-oxazolidin-3-yl group, 7-chloro-2-oxobenzo-1 ,, 3-oxazolidin-3-yl group, 5-bromo-2-oxobenzo-1,3-oxazolidin-3-yl group, 4-phenyl-2-oxobenzo-1,3-oxazolidin-3-yl group, 5-phenyl -2-oxobenzo-1,3-oxazolidin-3-yl group, 6-phenyl-2-oxobenzo-1,3-oxazolidin-3-yl group, 7-phenyl- Benzo-1,3-oxazolidinyl group such as oxobenzo-1,3-oxazolidin-3-yl group (on the benzo-1,3-oxazolidine ring, selected from the group consisting of oxo group, halogen atom and phenyl group Groups may be substituted by 1 to 3 groups).

  Imidazolidinyl group (On the imidazolidine ring, an oxo group, a phenyl C1 to 6 alkyl group [on the phenyl ring, a group selected from the group consisting of a halogen atom and a C1 to 6 alkoxy group is substituted by 1 to 3 And the like; and at least one member selected from the group consisting of phenyl group may be substituted), for example, imidazolidin-1-yl group, imidazolidin-2-yl group, imidazolidine -3-yl group, imidazolidin-4-yl group, imidazolidin-5-yl group, 3-benzyl-imidazolidin-1-yl group, 3,4-dibenzyl-2-oxoimidazolidin-1-yl group , 2-oxoimidazolidin-1-yl group, 3-benzyl-2-oxoimidazolidin-1-yl group, 3- (2-fluorobenzyl) -2-oxoimidazolide -1-yl group, 3- (3-fluorobenzyl) -2-oxoimidazolidin-1-yl group, 3- (4-fluorobenzyl) -2-oxoimidazolidin-1-yl group, 3-phenyl- 2-oxoimidazolidin-1-yl group, 3- (3,4-difluorobenzyl) -2-oxoimidazolidin-1-yl group, 3- (3,5-difluorobenzyl) -2-oxoimidazolidine- 1-yl group, 3- (3,4,5-trifluorobenzyl) -2-oxoimidazolidin-1-yl group, 3- (2-chlorobenzyl) -2-oxoimidazolidin-1-yl group, 3- (3-chlorobenzyl) -2-oxoimidazolidin-1-yl group, 3- (4-chlorobenzyl) -2-oxoimidazolidin-1-yl group, 3- (2,3-dichlorobenzyl) -2 Oxoimidazolidin-1-yl group, 3- (3,4-dichlorobenzyl) -2-oxoimidazolidin-1-yl group, 3- (3,5-dichlorobenzyl) -2-oxoimidazolidine-1-one -Yl, 3- (3,4,5-trichlorobenzyl) -2-oxoimidazolidin-1-yl, 3- (2-bromobenzyl) -2-oxoimidazolidin-1-yl, 3- ( 3-bromobenzyl) -2-oxoimidazolidin-1-yl group, 3- (4-bromobenzyl) -2-oxoimidazolidin-1-yl group, 3- (2-methoxybenzyl) -2-oxoimidazo Lysine-1-yl group, 3- (3-methoxybenzyl) -2-oxoimidazolidin-1-yl group, 3- (4-methoxybenzyl) -2-oxoimidazolidin-1-yl group, 3- ( 2 , 4-Dimethoxybenzyl) -2-oxoimidazolidin-1-yl group, 3- (2,4,6-trimethoxybenzyl) -2-oxoimidazolidin-1-yl group, 3- (3,5-) Dimethoxybenzyl) -2-oxoimidazolidin-1-yl group, 3- (4-ethoxybenzyl) -2-oxoimidazolidin-1-yl group, 3- (4-isopropoxybenzyl) -2-oxoimidazolidine -1-yl group, 3- (4-n-butoxybenzyl) -2-oxoimidazolidin-1-yl group, 3- (4-n-pentyloxybenzyl) -2-oxoimidazolidin-1-yl group , 3- (4-Hexyloxybenzyl) -2-oxoimidazolidin-1-yl group, 3- [2- (3-methoxy-4-chlorophenyl) ethyl] -2-oxoimidazolidine 1-yl group, 3- [3- (4-chlorophenyl) propyl] -2-oxoimidazolidin-1-yl group, 3- [4- (4-chlorophenyl) butyl] -2-oxoimidazolidine-1-one Group, 3- [5- (4-chlorophenyl) pentyl] -2-oxoimidazolidin-1-yl group, 3- [6- (4-chlorophenyl) hexyl] -2-oxoimidazolidin-1-yl group , 2-phenylimidazolidin-1-yl group, 3-phenyl-2-benzylimidazolidin-1-yl group, 3-phenyl-4-benzyl-2-oxoimidazolidin-1-yl group, 3-phenyl- Imidazolidinyl groups such as 5-benzyl-2-oxoimidazolidin-1-yl group, 4-phenyl-2-oxoimidazolidin-1-yl group, etc. A group consisting of a phenyl group, a phenyl C1-6 alkyl group [in which a group selected from the group consisting of a halogen atom and a C1-6 alkoxy group may be substituted on the phenyl ring] and a phenyl group One to three selected groups may be substituted. Can be mentioned.

  A benzimidazolidinyl group (on the benzimidazolidine ring, an oxo group, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group, an amino group which may have a C1-6 alkyl group as a substituent, C1 6 alkoxycarbonyl group and piperidyl group [in the piperidine ring, a C1-6 alkyl group, a phenyl group which may have 1 to 3 halogen atoms substituted on the phenyl ring, a C1-6 alkoxycarbonyl group and a phenyl C1 At least one group may be substituted with at least one group selected from the group consisting of at least one group selected from the group consisting of 6 alkoxycarbonyl groups; Imidazolidin-1-yl group, benzimidazolidin-2-yl group, benzimidazolidin-3-yl group, benzimi Zolidin-4-yl group, benzimidazolidin-5-yl group, benzimidazolidin-6-yl group, benzimidazolidin-7-yl group, 2-oxobenzimidazolidin-1-yl group, 3-methyl- 2-oxobenzimidazolidin-1-yl group, 3-methyl-benzoimidazolidin-1-yl group, 6-dimethylaminobenzimidazolidin-1-yl group, 6-ethoxycarbonylbenzoimidazolidin-1-yl group , 3- (4-phenylpiperidin-4-yl) benzoimidazolidin-1-yl group, 4-fluoro-benzoimidazolidin-1-yl group, 3-ethyl-2-oxobenzoimidazolidin-1-yl group , 3-n-propyl-2-oxobenzimidazolidin-1-yl group, 3-n-butyl-2-oxobenzimidazolidine 1-yl group, 3-n-pentyl-2-oxobenzimidazolidin-1-yl group, 3-n-hexyl-2-oxobenzimidazolidin-1-yl group, 3-methyl-6-fluoro-2 -Oxobenzimidazolidin-1-yl group, 3-methyl-4-fluoro-2-oxobenzimidazolidin-1-yl group, 3-methyl-5-fluoro-2-oxobenzimidazolidin-1-yl group , 3-methyl-7-fluoro-2-oxobenzimidazolidin-1-yl group, 3-methyl-6-chloro-2-oxobenzimidazolidin-1-yl group, 3-methyl-5-chloro-2 -Oxobenzimidazolidin-1-yl group, 3-methyl-4-chloro-2-oxobenzimidazolidin-1-yl group, 3-methyl-5-chloro-2-oxobenzoimida Zolidin-1-yl group, 3-methyl-7-chloro-2-oxobenzimidazolidin-1-yl group, 3-methyl-6-bromo-2-oxobenzimidazolidin-1-yl group, 3-methyl -4-bromo-2-oxobenzoimidazolidin-1-yl group, 3-methyl-5-bromo-2-oxobenzimidazolidin-1-yl group, 3-methyl-7-bromo-2-oxobenzo group Imidazolidin-1-yl group, 3-ethyl-6-fluoro-2-oxobenzimidazolidin-1-yl group, 3-isopropyl-6-fluoro-2-oxobenzimidazolidin-1-yl group, 3- n-Hexyl-6-fluoro-2-oxozones imidazolidin-1-yl group, 3-ethyl-6-chloro-2-oxobenzimidazolidin-1-yl group, 3-isopropyl 6-chloro-2-oxobenzimidazolidin-1-yl group, 3-n-hexyl-6-chloro-2-oxobenzoimidazolidin-1-yl group, 3-ethyl-5-chloro-2- Oxobenzimidazolidin-1-yl group, 3-isopropyl-5-chloro-2-oxobenzimidazolidin-1-yl group, 3-tert-butyl-5-chloro-2-oxobenzimidazolidin-1-yl group Group, 3-methyl-6-ethoxycarbonyl-2-oxobenzimidazolidin-1-yl group, 3-isopropyl-6-ethoxycarbonyl-2-oxobenzimidazolidin-1-yl group, 3-n-propyl- 6-Ethoxycarbonyl-2-oxobenzimidazolidin-1-yl group, 3-methyl-6-trifluoromethyl-2-oxobenzoimida Lysine-1-yl group, 5-trifluoromethyl-2-oxobenzimidazolidin-1-yl group, 3-methyl-5-trifluoromethyl-2-oxobenzimidazolidin-1-yl group, 3-isopropyl -5-trifluoromethyl-2-oxobenzimidazolidin-1-yl group, 3- (4-phenylpiperidin-1-yl) -2-oxobenzimidazolidin-1-yl group, 3- (4-phenyl) Piperidin-1-yl) -5-trifluoromethyl-2-oxobenzimidazolidin-1-yl group, 3- (4-phenylpiperidin-1-yl) -6-trifluoromethyl-2-oxobenzimidazolidine -1-yl group, 3-methyl-6-dimethylamino-2-oxobenzimidazolidin-1-yl group, 3-ethyl-6-dimethylamino -2-oxobenzimidazolidin-1-yl group, 3-methyl-6-amino-2-oxobenzoimidazolidin-1-yl group, 3-isopropyl-6-dimethylamino-2-oxobenzimidazolidine-1 -Yl group, 3- [4- (3-fluorophenyl) piperidin-1-yl] -2-oxobenzimidazolidin-1-yl group, 3- [4- (4-fluorophenyl) piperidin-1-yl group -2-oxobenzimidazolidin-1-yl group, 3- [4- (3-chlorophenyl) piperidin-1-yl] -2-oxobenzimidazolidin-1-yl group, 3- [4- (4) -Chlorophenyl) piperidin-1-yl] -2-oxobenzimidazolidin-1-yl group, 3- [4- (2,3-difluorophenyl) piperidin-1-yl] -5 Chloro-2-oxobenzimidazolidin-1-yl group, 3- [4- (4-fluorophenyl) piperidin-1-yl] -5-chloro-2-oxobenzimidazolidin-1-yl group, 3- [4- (2,4,6-Trichlorophenyl) piperidin-1-yl] -5-chloro-2-oxobenzimidazolidin-1-yl group, 3- [4- (4-chlorophenyl) piperidine-1-one Yl] -5-chloro-2-oxobenzimidazolidin-1-yl group, 3- [4- (3-fluorophenyl) piperidin-1-yl] -6-chloro-2-oxobenzimidazolidine-1-one Group, 3- [4- (4-iodophenyl) piperidin-1-yl] -6-chloro-2-oxobenzimidazolidin-1-yl group, 3- [4- (3-bromophenyl) pipe Gin-1-yl] -6-chloro-2-oxobenzimidazolidin-1-yl group, 3- [1-methylpiperidin-4-yl] -6-chloro-2-oxobenzimidazolidin-1-yl Group, 3- (piperidin-4-yl) -2-oxobenzimidazolidin-1-yl group, 3- (1-tert-butoxycarbonylpiperidin-4-yl) -2-oxobenzimidazolidin-1-yl group Group, 3- (benzyloxycarbonylpiperidin-4-yl) -2-oxobenzimidazolidin-1-yl group, 3- (piperidin-4-yl) -6-fluoro-2-oxobenzimidazolidine-1- Group, 3- (1-tert-butoxycarbonylpiperidin-4-yl) -6-fluoro-2-oxobenzimidazolidin-1-yl group, 3- (1- Benzyloxycarbonylpiperidin-4-yl) -6-fluoro-2-oxobenzimidazolidin-1-yl group, 3- (piperidin-4-yl) -6-chloro-2-oxobenzimidazolidin-1-yl Group, 3- (1-tert-butoxycarbonylpiperidin-4-yl) -6-chloro-2-oxobenzimidazolidin-1-yl group, 3- (1-benzyloxycarbonyl-4-piperidinyl) -6- Chloro-2-oxobenzimidazolidin-1-yl group, 3- (1,2-dimethylpiperidin-4-yl) benzoimidazolidin-1-yl group, 3- (1-benzyloxycarbonyl-2-methylpiperidine -4-yl) benzoimidazolidin-1-yl group, 3- (1,2,6-trimethylpiperidin-4-yl) benzimidazo And benzimidazolidinyl groups such as a zine-1-yl group (in which a oxo group, a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group, and a C1-6 alkyl group as a substituent group are disposed on the benzimidazolidine ring) Amino group which may have 2 to 2, C1-6 alkoxycarbonyl group and piperidyl group [C1-6 alkyl group on the piperidine ring, phenyl optionally substituted by 1 to 3 halogen atoms on the phenyl ring Group selected from the group consisting of C1-6 alkoxycarbonyl group and phenyl C1-6 alkoxycarbonyl group may be substituted by 1 to 3 groups substituted by 1 to 3 groups selected from the group consisting of It may be done. Can be mentioned.

  As a phthalimide group, a phthalimido 2-yl group etc. are mentioned, for example.

  As the indolinyl group (on the indoline ring, at least one member selected from the group consisting of a C1-6 alkyl group, a halogen atom and an oxo group may be substituted), for example, indolinin-1-yl Group, indolinin-2-yl group, indolinin-3-yl group, indolinin-4-yl group, indolinin-5-yl group, indolinin-6-yl group, indolinin-7-yl group, 3-methyl-indoline- 1-yl group, 3,8-dibromoindoline-1-yl group, 2-oxoindoline-1-yl group (alias: oxindole-1-yl group), 3-methyl-2-oxoindoline-1-yl group Group, 3,3-dimethyl-2-oxoindoline-1-yl group, 3-ethyl-2-oxoindoline-1-yl group, 3-n-propyl-2-oxoin Phosphorus-1-yl group, 3-n-butyl-2-oxoindoline-1-yl group, 3-n-pentyl-2-oxoindoline-1-yl group, 3-fluoro-2-oxoindoline-1-yl group Group, 3, 3-difluoro-2-oxoindoline-1-yl group, 3-chloro-2-oxoindoline-1-yl group, 3, 3-dichloro-2-oxoindoline-1-yl group, etc. (In the indoline ring, one to three groups selected from the group consisting of a C1-6 alkyl group, a halogen atom and an oxo group may be substituted).

  Examples of the 2,3-dihydrobenzisothiazolyl group (wherein at least one oxo group may be substituted on the 2,3-dihydrobenzisothiazole ring) include, for example, 3-benzoisothiazolidinone -1,1-dioxide-2-yl group etc. can be mentioned.

  As the 1H-2,4-benzoxazinyl group (at least one oxo group may be substituted on the 1H-2,4-benzoxazine ring), 1H-2,4-benzoxazine Examples include -3 (4H) -on-4-yl group and 1H-2,4-benzoxazine-1,3 (4H) -dione-4-yl group.

  As phenoxy C1-6 alkyl group which may have a halogen atom as a substituent on a phenyl ring, for example, phenoxymethyl group, 2-fluorophenoxymethyl group, 3-fluorophenoxymethyl group, 3,4-difluorophenoxymethyl group Group, 3,5-difluorophenoxymethyl group, 2,3,4,5,6-pentafluorophenoxymethyl group, 2-chlorophenoxymethyl group, 3-chlorophenoxymethyl group, 4-chlorophenoxymethyl group, 3, 4-dichlorophenoxymethyl group, 3,5-dichlorophenoxymethyl group, 2-phenoxyethyl group, 1-phenoxyethyl group, 3-phenoxypropyl group, 4-phenoxybutyl group, 5-phenoxypentyl group, 6-phenoxyhexyl group Group, 2- (2,4,6-chlorophenoxy) And phenyl rings such as 3- (4-iodophenoxy) propyl, 4- (4-bromophenoxy) butyl, 5- (4-chlorophenoxy) pentyl and 6- (4-chlorophenoxy) hexyl. The phenoxy C1-6 alkyl group which may be substituted by 1-5 halogen atoms can be mentioned to the top.

  Examples of the phenyl C2-6 alkenyl group which may have a halogen atom as a substituent on the phenyl ring include, for example, 3-phenyl-2-propenyl group (common name: cinnamyl group), 4-phenyl-2-butenyl group, 4-phenyl-3-butenyl group, 4-phenyl-1,3-butadienyl group, 5-phenyl-1,3,5-hexatrienyl group, 3- (2-fluorophenyl) -2-propenyl group, 3 -(3-fluorophenyl) -2-propenyl group, 3- (4-fluorophenyl) -2-propenyl group, 3- (2,3-difluorophenyl) -2-propenyl group, 3- (2,3, 3- 4,5,6-pentafluorophenyl) -2-propenyl group, 3- (3,4-difluorophenyl) -2-propenyl group, 3- (3,5-difluorophenyl) -2-prop Penyl group, 3- (2,4,6-trichlorophenyl) -2-propenyl group, 3- (3-chlorophenyl) -2-propenyl group, 3- (4-chlorophenyl) -2-propenyl group, 3- ( 2,3-Dichlorophenyl) -2-propenyl group, 3- (2,4-dichlorophenyl) -2-propenyl group, 3- (3,4-dichlorophenyl) -2-propenyl group, 3- (3,5-dichlorophenyl) ) -2-Propenyl group, 3- (2-bromophenyl) -2-propenyl group, 3- (3-bromophenyl) -2-propenyl group, 3- (4-bromophenyl) -2-propenyl group, 4 -(4-chlorophenyl) -2-butenyl group, 4- (4-chlorophenyl) -3-butenyl group, 5- (4-chlorophenyl) -2-pentenyl group, 5- (4-chlorophenyl) 4-pentenyl group, 5- (4-chlorophenyl) -3-pentenyl group, 6- (4-chlorophenyl) -5-hexenyl group, 6- (4-chlorophenyl) -4-hexenyl group, 6- (4-chlorophenyl) -3-hexenyl group It may have 1 to 5 halogen atoms on the phenyl ring such as chlorophenyl) -3-hexenyl group, 6- (4-chlorophenyl) -3-hexenyl group, etc. phenyl C2 having 1 to 2 double bonds 6 alkenyl groups can be mentioned.

  At least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group, a halogen-substituted or unsubstituted C1-6 alkoxy group and a phenyl group as a substituent on the phenyl ring is substituted As the phenyl group which may be substituted, for example, phenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 2-chlorophenyl group Bromophenyl group, 3-bromophenyl group, 4-bromophenyl group, 2-iodophenyl group, 3-iodophenyl group, 4-iodophenyl group, 2,3-difluorophenyl group, 3,4-difluorophenyl group, 3,5-difluorophenyl group, 2,4-difluorophenyl group, 2,6-difluorophenyl 2,3-dichlorophenyl group, 3,4-dichlorophenyl group, 3,5-dichlorophenyl group, 2,4-dichlorophenyl group, 2,6-dichlorophenyl group, 3,4,5-trifluorophenyl group, 3,4 5, 5-trichlorophenyl group, 2,4,6-trifluorophenyl group, 2,4,6-trichlorophenyl group, 2-fluoro-4-bromophenyl group, 4-chloro-3-fluorophenyl group, 2 ,, 3,4-Trichlorophenyl group, 3,4,5-trifluorophenyl group, 2,4,6-tribromophenyl group, 4-n-butylphenyl group, 2,4-dimethylphenyl group, 2,3- Dimethylphenyl group, 2,6-dimethylphenyl group, 3,5-dimethylphenyl group, 2,5-dimethylphenyl group, 2,4,6-trimethylphenyl group, 3,5 Ditrifluoromethylphenyl group, 4-n-butoxyphenyl group, 2,4-dimethoxyphenyl group, 2,3-dimethoxyphenyl group, 2,6-dimethoxyphenyl group, 3,5-dimethoxyphenyl group, 2,5- Dimethoxyphenyl group, 2,4,6-trimethoxyphenyl group, 3,5-ditrifluoromethoxyphenyl group, 3-chloro-4-methoxyphenyl group, 2-chloro-4-trifluoromethoxyphenyl group, 3-methyl -4-fluorophenyl group, 4-bromo-3-trifluoromethylphenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 2-methyl-3-chlorophenyl group, 3-methyl- 4-chlorophenyl group, 2-chloro-4-methylphenyl group, 2-methyl-3-fluorophenyl group, 2-trile Fluoromethylphenyl group, 3-trifluoromethylphenyl group, 4-trifluoromethylphenyl group, 2-pentafluoroethylphenyl group, 3-pentafluoroethylphenyl group, 4-pentafluoroethylphenyl group, 2-isopropylphenyl group , 3-isopropylphenyl group, 4-isopropylphenyl group, 2-tert-butylphenyl group, 3-tert-butylphenyl group, 4-tert-butylphenyl group, 2-sec-butylphenyl group, 3-sec-butyl Phenyl group, 4-sec-butylphenyl group, 2-n-heptafluoropropylphenyl group, 3-n-heptafluoropropylphenyl group, 4-n-heptafluoropropylphenyl group, 4-pentylphenyl group, 4-hexyl Phenyl group, 2-methoxyphenyl , 3-methoxyphenyl group, 4-methoxyphenyl group, 3-chloro-2-methoxyphenyl group, 2-fluoro-3-methoxyphenyl group, 2-fluoro-4-methoxyphenyl group, 2,6-dimethoxyphenyl group , 2,3,4-Trifluorophenyl group, 2,3,4,5,6-pentafluorophenyl group, 2-trifluoromethoxyphenyl group, 3-trifluoromethoxyphenyl group, 4-trifluoromethoxyphenyl group , 3-fluoro-2-trifluoromethoxyphenyl group, 2-fluoro-3-trifluoromethoxyphenyl group, 3-fluoro-4-trifluoromethoxyphenyl group, 3-chloro-2-trifluoromethoxyphenyl group, 2 -Chloro-3-trifluoromethoxyphenyl group, 3-chloro-4-trifluoromethoxy , 2-pentafluoroethoxyphenyl group, 3-pentafluoroethoxyphenyl group, 4-pentafluoroethoxyphenyl group, 3-chloro-2-pentafluoroethoxyphenyl group, 2-chloro-3-pentafluoroethoxyphenyl group , 3-chloro-4-pentafluoroethoxyphenyl group, 2-isopropoxyphenyl group, 3-isopropoxyphenyl group, 4-isopropoxyphenyl group, 2-tert-butoxyphenyl group, 3-tert-butoxyphenyl group, 4-tert-butoxyphenyl group, 2-sec-butoxyphenyl group, 3-sec-butoxyphenyl group, 4-sec-butoxyphenyl group, 2-n-heptafluoropropoxyphenyl group, 3-n-heptafluoropropoxyphenyl group Group, 4-n-heptaf A halogen atom, a halogen atom or a halogen atom on a phenyl ring such as fluoropropoxyphenyl group, 4-n-pentoxyphenyl group, 4-n-hexyloxyphenyl group, 4-biphenylyl group, 3-biphenylyl group and 2-biphenylyl group Phenyl optionally substituted by 1 to 5, preferably 1 to 3 groups selected from the group consisting of unsubstituted C1-6 alkyl groups, halogen-substituted or unsubstituted C1-6 alkoxy groups and phenyl groups Groups can be mentioned.

  1,3-thiazolidinyl group (phenyl C1-6 alkylidene which may have halogen-substituted or unsubstituted C1-6 alkyl group on oxo group and phenyl ring as a substituent group on 1,3-thiazolidine ring As the group in which at least one group selected from the group consisting of groups may be substituted), for example, 1,3-thiazolidin-2-yl group, 1,3-thiazolidin-3-yl group, 1,3 -Thiazolidin-4-yl group, 1,3-thiazolidin-5-yl group, 1,3-thiazolidine-2,4-dione-3-yl group, 5-benzylidene-1,3-thiazolidin-3-yl group 5-benzylidene-1,3-thiazolidine-2, on-3-yl group, 5-benzylidene-1,3-thiazolidin-4-on-3-yl group, 5- (2-methylbenzylidene) -1, 3- Azolizin-3-yl group, 5- (2,4-dimethylbenzylidene) -1,3-thiazolidin-3-yl group, 5- (2,4,6-trimethylbenzylidene) -1,3-thiazolidine-3- , 5-benzylidene-1,3-thiazolidine-2,4-dione-3-yl group, 5- (2-trifluoromethylbenzylidene) -1,3-thiazolidine-2,4-dione-3-yl Group, 5- (3,5-ditrifluoromethylbenzylidene) -1,3-thiazolidine-2,4-dione-3-yl group, 5- (4-trifluoromethylbenzylidene) -1,3-thiazolidine-2 , 4-dione-3-yl group, 5- [2- (4-trifluoromethylphenyl) ethylidene] -1,3-thiazolidine-2,4-dione-3-yl group, 5- [3- (4) -Trifluoro Methylphenyl) propylidene] -1,3-thiazolidine-2,4-dione-3-yl group, 5- [4- (4-trifluoromethylphenyl) butylidene] -1,3-thiazolidine-2,4-dione -3-yl group, 5- [5- (4-trifluoromethylphenyl) pentylidene] -1,3-thiazolidine-2,4-dione-3-yl group, 5- [6- (4-trifluoromethyl) group 1,3-thiazolidinyl groups such as phenyl) hexylidene] -1,3-thiazolidine-2,4-dione-3-yl group (as in the case of a 1,3-thiazolidine ring, an oxo group as a substituent and a phenyl ring) And 1-3 groups optionally selected from the group consisting of phenyl C1-6 alkylden groups which may have 1 to 3 halogen-substituted or unsubstituted C1-6 alkyl groups may be mentioned. be able to.

  As a halogen substituted or unsubstituted phenyl group, for example, phenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 2 -Bromophenyl group, 3-bromophenyl group, 4-bromophenyl group, 2-iodophenyl group, 3-iodophenyl group, 4-iodophenyl group, 2,3-difluorophenyl group, 3,4-difluorophenyl group , 3,5-difluorophenyl group, 2,4-difluorophenyl group, 2,6-difluorophenyl group, 2,3-dichlorophenyl group, 3,4-dichlorophenyl group, 3,5-dichlorophenyl group, 2,4- Dichlorophenyl group, 2,6-dichlorophenyl group, 3,4,5-trifluorophenyl group, 3 4,5-Trichlorophenyl group, 2,4,6-trifluorophenyl group, 2,4,6-trichlorophenyl group, 2-fluoro-4-bromophenyl group, 4-chloro-3-fluorophenyl group, 2 , 3,4-trichlorophenyl group, 3,4,5-trifluorophenyl group, 2,4,6-trifluorophenyl group, 2,3,4,5,6-pentafluorophenyl group, etc. on a phenyl ring And a phenyl group which may be substituted by 1 to 5 halogen atoms.

  Examples of the phenyl C1-6 alkyl group which may have a phenyl group as a substituent on the phenyl ring include, for example, benzyl group, 2-phenylethyl group, 1-phenylethyl group, 3-phenylpropyl group, 4-phenylbutyl Group, 5-phenylpentyl group, 6-phenylhexyl group, 2-methyl-3-phenylpropyl group, 1,1-dimethyl-2-phenylethyl group, 3-phenylbenzyl group, 2-phenylbenzyl group, 4- The phenyl C1-6 alkyl group which may have 1 to 3 phenyl groups as a substituent on a phenyl ring such as phenylbenzyl group, 2,4-diphenylbenzyl group, 2,4,6-triphenylbenzyl group is mentioned be able to.

Phenyl group (on the phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group, a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group, an amino group [C.sub.1-6 alkyl group on an amino group, Phenyl group (in which at least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group is substituted on a phenyl ring At least one of a group selected from the group consisting of (optional) may be substituted], a phenoxy group [on the phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted group Or at least one group selected from the group consisting of unsubstituted C.sub.1-6 alkoxy groups may be substituted] and Lysyl group [in the piperidine ring, at least one phenoxy group (on the phenyl ring, a group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group. As at least one kind of the group selected from the group consisting of the group consisting of the group consisting of the group consisting of], for example, Phenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 2-bromophenyl group, 3-bromophenyl group, 4- Bromophenyl group, 2-iodophenyl group, 3-iodophenyl group, 4-iodophenyl group, 2,3-difluorophenyl group, , 3,4,5,6-pentafluorophenyl group, 3,4-difluorophenyl group, 3,5-difluorophenyl group, 2,4-difluorophenyl group, 2,6-difluorophenyl group, 2,3- Dichlorophenyl group, 3,4-dichlorophenyl group, 3,5-dichlorophenyl group, 2,4-dichlorophenyl group, 2,6-dichlorophenyl group, 3,4,5-trifluorophenyl group, 3,4,5-trichlorophenyl group Group, 2,4,6-trifluorophenyl group, 2,4,6-trichlorophenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 2,4-dimethylphenyl group, 2 , 4,6-trimethylphenyl group, 2-methyl-3-chlorophenyl group, 3-methyl-4-chlorophenyl group, 2-chloro-4-methylphenyl group Group, 2-methyl-3-fluorophenyl group, 2-trifluoromethylphenyl group, 3-trifluoromethylphenyl group, 3,5-ditrifluoromethylphenyl group, 4-trifluoromethylphenyl group, 2-pentacene group Fluoroethylphenyl group, 3-pentafluoroethylphenyl group, 4-pentafluoroethylphenyl group, 2-isopropylphenyl group, 3-isopropylphenyl group, 4-isopropylphenyl group, 2-tert-butylphenyl group, 3-tert -Butylphenyl group, 4-tert-butylphenyl group, 2-sec-butylphenyl group, 3-sec-butylphenyl group, 4-sec-butylphenyl group, 2-n-heptafluoropropylphenyl group, 3-n -Heptafluoropropylphenyl group, 4-n-heptaful Ropropylphenyl group, 4-pentylphenyl group, 4-hexylphenyl group, 2-methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 2-methoxy-3-chlorophenyl group, 2-fluoro-3- Methoxyphenyl group, 2-fluoro-4-methoxyphenyl group, 2,6-dimethoxyphenyl group, 2,4,6-trimethoxyphenyl group, 2-trifluoromethoxyphenyl group, 3-trifluoromethoxyphenyl group, 3 5-Ditrifluoromethoxyphenyl group, 4-trifluoromethoxyphenyl group, 2-pentafluoroethoxyphenyl group, 3-pentafluoroethoxyphenyl group, 4-pentafluoroethoxyphenyl group, 2-isopropoxyphenyl group, 3- Isopropoxyphenyl group, 4-isopropoxy group Group, 2-tert-butoxyphenyl group, 3-tert-butoxyphenyl group, 4-tert-butoxyphenyl group, 2-sec-butoxyphenyl group, 3-sec-butoxyphenyl group, 4-sec-butoxyphenyl group , 2-n-heptafluoropropoxyphenyl group, 3-n-heptafluoropropoxyphenyl group, 4-n-heptafluoropropoxyphenyl group, 4-pentyloxyphenyl group, 4-hexyloxyphenyl group, 2-aminophenyl group 3-aminophenyl group, 4-aminophenyl group, 3-methylaminophenyl group, 3-dimethylaminophenyl group, 4-methylaminophenyl group, 4-dimethylaminophenyl group, 4-ethylaminophenyl group, 4- Diethylaminophenyl group, 4-n-propylaminopheny Group, 4-di-n-propylaminophenyl group, 4-n-butylaminophenyl group, 4-di-n-butylaminophenyl group, 4-n-pentylaminophenyl group, 4-di-n-pentyl group Aminophenyl group, 4-n-hexylaminophenyl group, 4-di-n-hexylaminophenyl group, 4-phenylaminophenyl group, 4- (2-fluorophenylamino) phenyl group, 4- (3-fluorophenyl) Amino) phenyl group, 4- (4-fluorophenylamino) phenyl group, 4- (2,3,4,5,6-pentafluorophenylamino) phenyl group, 4- (2,4-difluorophenylamino) phenyl Group, 4- (3,4-difluorophenylamino) phenyl group, 4- (3,5-difluorophenylamino) phenyl group, 4- (2-chlorophenyl) Nylamino) phenyl group, 4- (3-chlorophenylamino) phenyl group, 4- (4-chlorophenylamino) phenyl group, 4- (2-bromophenylamino) phenyl group, 4- (3-bromophenylamino) phenyl group 4- (4-Bromophenylamino) phenyl group, 4- (2,3-dichlorophenylamino) phenyl group, 4- (2,4-dichlorophenylamino) phenyl group, 4- (2,4,6-trichlorophenyl) Amino) phenyl group, 4- (3,5-dichlorophenylamino) phenyl group, 4- (2-methylphenylamino) phenyl group, 4- (3-methylphenylamino) phenyl group, 4- (4-methylphenylamino) ) Phenyl group, 4- (2-ethylphenylamino) phenyl group, 4- (3-ethylphenylamino) phenyl Group, 4- (4-ethylphenylamino) phenyl group, 4- (4-n-propylphenylamino) phenyl group, 4- (4-tert-butylphenylamino) phenyl group, 4- (4-n-butyl group) Phenylamino) phenyl group, 4- (2-trifluoromethylphenylamino) phenyl group, 4- (3-trifluoromethylphenylamino) phenyl group, 4- (4-trifluoromethylphenylamino) phenyl group, 4- (2-Pentafluoroethylphenylamino) phenyl group, 4- (3-pentafluoroethylphenylamino) phenyl group, 4- (2,3-dimethylphenylamino) phenyl group, 4- (3,4,5-trimethyl) Phenylamino) phenyl group, 4- (4-pentylphenylamino) phenyl group, 4- (4-hexylphenylamide) B) phenyl group, 4- (2-trifluoromethoxyphenylamino) phenyl group, 4- (3-trifluoromethoxyphenylamino) phenyl group, 4- (3-methoxyphenylamino) phenyl group, 4- (2, 4-dimethoxyphenylamino) phenyl group, 4- (2,4,6-trimethoxyphenylamino) phenyl group, 4- (4-trifluoromethoxyphenylamino) phenyl group, 4- (2-pentafluoroethoxyphenylamino) ) Phenyl group, 4- (3-pentafluoroethoxyphenylamino) phenyl group, 4- (4-pentafluoroethoxyphenylamino) phenyl group, 3- (N-methyl-N-phenylamino) phenyl group, 2-phenoxy Phenyl group, 3-phenoxyphenyl group, 4-phenoxyphenyl group, 2- (2-q) Rophenoxy) phenyl group, 2,4-diphenoxyphenyl group, 2- (3-chlorophenoxy) phenyl group, 2- (4-chlorophenoxy) phenyl group, 3- (2-chlorophenoxy) phenyl group, 3- (3-chlorophenoxy) phenyl group, 3- (4-chlorophenoxy) phenyl group, 4- (2-chlorophenoxy) phenyl group, 4- (2,3-dichlorophenoxy) phenyl group, 4- (2,4 (2,4) , 6-Trichlorophenoxy) phenyl group, 2- (2-trifluoromethylphenoxy) phenyl group, 2- (3-trifluoromethylphenoxy) phenyl group, 2- (4-trifluoromethylphenoxy) phenyl group, 3- (2-trifluoromethylphenoxy) phenyl group, 3- (3-trifluoromethylphenoxy) phenyl group, 3- (2 3,4,5,6-Pentafluoromethylphenoxy) phenyl group, 4- (2-trifluoromethylphenoxy) phenyl group, 4- (3-methylphenoxy) phenyl group, 4- (2,4-dimethylphenoxy) Phenyl group, 4- (2,4,6-trimethylphenoxy) phenyl group, 4- (3-trifluoromethylphenoxy) phenyl group, 4- (4-trifluoromethylphenoxy) phenyl group, 2- (2-trimethylphenoxy) phenyl group Fluoromethoxyphenoxy) phenyl group, 2- (3-trifluoromethoxyphenoxy) phenyl group, 2- (4-trifluoromethoxyphenoxy) phenyl group, 2- (4-methoxyphenoxy) phenyl group, 2- (2,4 -Dimethoxyphenoxy) phenyl group, 2- (2,4,6-trimethoxyphenoxy) phenyl group, 3- ( 2-trifluoromethoxyphenoxy) phenyl group, 3- (3-trifluoromethoxyphenoxy) phenyl group, 3- (4-trifluoromethoxyphenoxy) phenyl group, 4- (2-trifluoromethoxyphenoxy) phenyl group, 4 -(3-trifluoromethoxyphenoxy) phenyl group, 4- (4-trifluoromethoxyphenoxy) phenyl group, 2- (4-phenoxypiperidin-1-yl) phenyl group, 3- (4-phenoxypiperidine-1-) Yl) phenyl group, 4- (4-phenoxypiperidin-1-yl) phenyl group, 2- [4- (4-chlorophenoxy) piperidin-1-yl] phenyl group, 4- [4- (4-chlorophenoxy) ) Piperidin-1-yl] phenyl group, 3- [4- (2,4,6-trichlorophenoxy) pipe Gin-1-yl] phenyl group, 4- [4- (3,4-dichlorophenoxy) piperidin-1-yl] phenyl group, 4- [4- (2,3,4,5,6-pentafluorophenoxy] ) Piperidin-1-yl] phenyl group, 4- [4- (4-bromophenoxy) piperidin-1-yl] phenyl group, 3- [4- (4-chlorophenoxypiperidin-1-yl) phenyl group, 2 -[4- (4-Methylphenoxy) piperidin-1-yl] phenyl group, 2- [4- (3,4-dimethylphenoxy) piperidin-1-yl] phenyl group, 2- [4- (3,4) 5-trimethylphenoxy) piperidin-1-yl] phenyl group, 3- [4- (4-trifluoromethylphenoxy) piperidin-1-yl] phenyl group, 4- [4- (4-trifluoromethyl) Henoxy) piperidin-1-yl] phenyl group, 3- [4- (4-pentafluoroethyl phenoxy) piperidin-1-yl] phenyl group, 4- [4- (4-pentafluoroethyl phenoxy) piperidine-1-] Yl] phenyl group, 2- [4- (4-trifluoromethoxyphenoxypiperidin-1-yl) phenyl group, 3- [4- (4-trifluoromethoxyphenoxy) piperidin-1-yl] phenyl group, 4- [4- (4-Methoxyphenoxy) piperidin-1-yl] phenyl group, 4- [4- (2,4-dimethoxyphenoxy) piperidin-1-yl] phenyl group, 4- [4- (2,4,4,4 6-trimethoxyphenoxy) piperidin-1-yl] phenyl group, 4- [4- (4-trifluoromethoxyphenoxy) piperidin-1-yl A phenyl group, 2- [4- (4-pentafluoroethoxyphenoxy) piperidin-1-yl] phenyl group, 4- [4- (4-pentafluoroethoxyphenoxy) piperidin-1-yl] phenyl group, (3 , 4-Diphenoxypiperidin-1-yl) phenyl group,


A phenyl group such as a peridin-1-ylphenyl group, a (3,4,5-triphenoxypiperidin-1-yl) phenyl group, a piperidin-4-ylphenyl group (on the phenyl ring, a halogen atom, halogen substitution or Unsubstituted C1-6 alkyl group and halogen substituted or unsubstituted C1-6 alkoxy group, amino group [C1-6 alkyl group and phenyl group (on halogen group, halogen atom on halogen ring, halogen substituted or substituted From 1 to 5, preferably 1 to 3 groups selected from the group consisting of unsubstituted C1-6 alkyl groups and halogen-substituted or unsubstituted C1-6 alkoxy groups; The selected group may be substituted by 1 to 2), phenoxy group [on the phenyl ring, a halogen atom, halogen substituted or unsubstituted C1 to C6] 1-5 is a group selected from the group consisting of C1~6 alkoxy alkyl group and halogen-substituted or unsubstituted, preferably it may be in 1-3 substituents. And a piperidyl group [on a piperidine ring, as a substituent, a phenoxy group (on a phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group, and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group. 1 to 5 groups, preferably 1 to 3 groups, and 1 to 3 groups may optionally be substituted); and 1 to 5 groups selected from the group consisting of And preferably 1 to 3) may be mentioned.

  Piperazinyl C1-6 alkyl group (in the piperazine ring, C1-6 alkoxycarbonyl group and phenyl C1-6 alkoxycarbonyl group [in the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group, a halogen 1 to 3 groups selected from the group consisting of a substituted or unsubstituted C1-6 alkoxy group and a phenyl group may be substituted], at least one of the groups selected from the group consisting of And 2- (2-piperazinyl) ethyl group, 1- (3-piperazinyl) ethyl group, 3- (4-piperazinyl) propyl group, 4- (1). -Piperazinyl) butyl group, 5- (2-piperazinyl) pentyl group, 6- (3-piperazinyl) hexyl group, 4-methoxycarbonyl-1-yl Perazinylmethyl group, 2- (4-methoxycarbonyl-1-piperazinyl) ethyl group, 3- (4-methoxycarbonyl-1-piperazinyl) propyl group, 4- (4-methoxycarbonyl-1-piperazinyl) butyl group, 5- (4-Methoxycarbonyl-1-piperazinyl) pentyl group, 6- (4-methoxycarbonyl-1-piperazinyl) hexyl group, 4-ethoxycarbonyl-1-piperazinylmethyl group, 2- (4-ethoxycarbonyl-1 group) -Piperazinyl) ethyl group, 3- (4-ethoxycarbonyl-1-piperazinyl) propyl group, 4- (4-ethoxycarbonyl-1-piperazinyl) butyl group, 5- (4-ethoxycarbonyl-1-piperazinyl) pentyl group , 6- (4-Ethoxycarbonyl-1-piperazinyl) hexyl group, 4 tert-butoxycarbonyl-1-piperazinylmethyl group, 2- (4-tert-butoxycarbonyl-1-piperazinyl) ethyl group, 3- (4-tert-butoxycarbonyl-1-piperazinyl) propyl group, 4- (4- (4-tert-butoxycarbonyl-1-piperazinyl) propyl group 4-tert-butoxycarbonyl-1-piperazinyl) butyl group, 5- (4-tert-butoxycarbonyl-1-piperazinyl) pentyl group, 6- (4-tert-butoxycarbonyl-1-piperazinyl) hexyl group, 2- (4-biphenylylmethoxycarbonyl-1-piperazinyl) ethyl group, 3- (4-biphenylylmethoxycarbonyl-1-piperazinyl) propyl group, 4- (4-biphenylylmethoxycarbonyl-1-piperazinyl) butyl group, 5 -(4-Biphenylylmethoxycarbonyl-1-pipera Dinyl) pentyl group, 6- (4-biphenylylmethoxycarbonyl-1-piperazinyl) hexyl group, 2- (4-benzyloxycarbonyl-1-piperazinyl) ethyl group, 3- (4-benzyloxycarbonyl-1-piperazinyl) ) Propyl, 4- (4-benzyloxycarbonyl-1-piperazinyl) butyl, 5- (4-benzyloxycarbonyl-1-piperazinyl) pentyl, 6- (4-benzyloxycarbonyl-1-piperazinyl) hexyl Group, 2- (4- (2-fluorobenzyloxycarbonyl) -1-piperazinyl) ethyl group, 3- (4- (2-fluorobenzyloxycarbonyl) -1-piperazinyl) propyl group, 4- (4- (4- (2-fluorobenzyloxycarbonyl)) 2,3-Difluorobenzyloxycarbonyl) -1-piperazinyl) butyl group, -(4- (2-Fluorobenzyloxycarbonyl) -1-piperazinyl) pentyl, 6- (4- (4-fluorobenzyloxycarbonyl) -1-piperazinyl) hexyl, 3- (4- (3-fluoro) Benzyloxycarbonyl) -1-piperazinyl) propyl group, 4- (4- (3-fluorobenzyloxycarbonyl) -1-piperazinyl) butyl group, 5- (4- (3-fluorobenzyloxycarbonyl) -1-piperazinyl ) Pentyl group, 3- (4- (4-fluorobenzyloxycarbonyl) -1-piperazinyl) propyl group, 4- (4- (4-fluorobenzyloxycarbonyl) -1-piperazinyl) butyl group, 5- (4 -(4-Fluorobenzyloxycarbonyl) -1-piperazinyl) pentyl group, 6- (4- (4- (4-) Fluorobenzyloxycarbonyl) -1-piperazinyl) hexyl group, 2- (4- (2,3-dichlorobenzyloxycarbonyl) -1-piperazinyl) ethyl group, 3- (4- (2-chlorobenzyloxycarbonyl) group -1-piperazinyl) propyl group, 4- (4- (2-chlorobenzyloxycarbonyl) -1-piperazinyl) butyl group, 5- (4- (2,4,6-trichlorobenzyloxycarbonyl) -1-piperazinyl ) Pentyl group, 6- (4- (2-chlorobenzyloxycarbonyl) -1-piperazinyl) hexyl group, 2- (4- (3-chlorobenzyloxycarbonyl) -1-piperazinyl) ethyl group, 3- (4 -(3-Chlorobenzyloxycarbonyl) -1-piperazinyl) propyl group, 4- (4- (3-chlorobenzyl) Oxycarbonyl) -1-piperazinyl) butyl group, 5- (4- (3-chlorobenzyloxycarbonyl) -1-piperazinyl) pentyl group, 6- (3-chloro-4-methylbenzyloxycarbonyl-1-piperazinyl) Hexyl group, 2- (4- (4-chlorobenzyloxycarbonyl) -1-piperazinyl) ethyl group, 3- (4- (4-chlorobenzyloxycarbonyl) -1-piperazinyl) propyl group, 4- (4- (4-chlorobenzyloxycarbonyl) -1-piperazinyl) group (4-chloro-3-methoxybenzyloxycarbonyl) -1-piperazinyl) butyl group, 5- (4- (4-chlorobenzyloxycarbonyl) -1-piperazinyl) pentyl group, 6- (4-chlorobenzyloxycarbonyl) -1-piperazinyl) hexyl group, 2- (4- (2-methylbenzyloxycarbonyl) -1 -Piperazinyl) methyl group, 2- (4- (2,4-dimethylbenzyloxycarbonyl) -1-piperazinyl) methyl group, 2- (4- (2,4,6-trimethylbenzyloxycarbonyl) -1-piperazinyl ) Methyl group, 2- (4- (2-trifluoromethylbenzyloxycarbonyl) -1-piperazinyl) ethyl group, 3- (4- (3,5-ditrifluoromethylbenzyloxycarbonyl) -1-piperazinyl) propyl Group, 4- (4- (2-trifluoromethylbenzyloxycarbonyl) -1-piperazinyl) butyl group, 5- (4- (2-trifluoromethylbenzyloxycarbonyl) -1-piperazinyl) pentyl group, 6- (4- (2-trifluoromethylbenzyloxycarbonyl) -1-piperazinyl) hexyl group, 3- 4- (3-trifluoromethylbenzyloxycarbonyl) -1-piperazinyl) propyl group, 4- (4- (3-trifluoromethylbenzyloxycarbonyl) -1-piperazinyl) butyl group, 5- (4- (3) -Trifluoromethylbenzyloxycarbonyl) -1-piperazinyl) pentyl, 3- (4- (4-trifluoromethylbenzyloxycarbonyl) -1-piperazinyl) propyl, 4- (4- (4-trifluoromethyl) Benzyloxycarbonyl) -1-piperazinyl) butyl group, 5- (4- (4-trifluoromethylbenzyloxycarbonyl) -1-piperazinyl) pentyl group, 6- (4- (4-trifluoromethylbenzyloxycarbonyl) -1-piperazinyl) hexyl group, 2- (4- (3,5-ditriful) Lomethoxybenzyloxycarbonyl) -1-piperazinyl) ethyl group, 2- (4- (2-methoxybenzyloxycarbonyl) -1-piperazinyl) methyl group, 2- (4- (2,4-dimethoxybenzyloxycarbonyl) -1-piperazinyl) methyl group, 2- (4- (2,4,6-trimethoxybenzyloxycarbonyl) -1-piperazinyl) methyl group, 3- (4- (2-trifluoromethoxybenzyloxycarbonyl)- 1-piperazinyl) propyl group, 4- (4- (2-trifluoromethoxybenzyloxycarbonyl) -1-piperazinyl) butyl group, 5- (4- (2-trifluoromethoxybenzyloxycarbonyl) -1-piperazinyl) A pentyl group, 6- (4- (2-trifluoromethoxybenzyloxycarbonyl) -1-piperazinyl) hexyl group, 3- (4- (3-trifluoromethoxybenzyloxycarbonyl) -1-piperazinyl) propyl group, 4- (4- (3-trifluoromethoxybenzyloxycarbonyl) -1-piperazinyl ) Butyl group, 5- (4- (3-trifluoromethoxybenzyloxycarbonyl) -1-piperazinyl) pentyl group, 3- (4- (4-trifluoromethoxybenzyloxycarbonyl) -1-piperazinyl) propyl group, 4- (4- (4-trifluoromethoxybenzyloxycarbonyl) -1-piperazinyl) butyl group, 5- (4- (4-trifluoromethoxybenzyloxycarbonyl) -1-piperazinyl) pentyl group, 6- (4 -(4-Trifluoromethoxybenzyloxycarbonyl) -1-pipera Piperazinyl C1-6 alkyl groups such as nyl) hexyl group, (3,4-diethoxycarbonyl-1-piperazinyl) methyl group, 4-phenylmethoxycarbonyl-2,5-dimethoxycarbonyl-1-piperazinyl) methyl group (Ci.sub.1-6 alkoxycarbonyl group and phenyl C.sub.1-6 alkoxycarbonyl group on the piperazine ring [in the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group, a halogen substituted or unsubstituted C.sub.1 Groups selected from the group consisting of -6 alkoxy group and phenyl group may be substituted by 1 to 3 groups] may be substituted 1 to 3 groups selected from the group consisting of .

  Piperazinylcarbonyl C1-6 alkyl group (C1-6 alkoxycarbonyl group on the piperazine ring, phenyl C1 optionally having halogen-substituted or unsubstituted C1-6 alkyl group as a substituent on the phenyl ring To 6 alkoxycarbonyl group and phenyl C1-6 alkyl group [wherein at least one group selected from the group consisting of halogen-substituted or unsubstituted C1-6 alkyl group and phenyl group is substituted on the phenyl ring And the like.) At least one of a group selected from the group consisting of (1) may be substituted), for example, 1-piperazinylcarbonylmethyl group, 2- (2-piperazinylcarbonyl) ethyl group, 1- (3-piperazinylcarbonyl) ethyl group, 3- (4-piperazinylcarbonyl) propyl group, 4- (1-piperazinyl) Rubonyl) butyl group, 5- (2-piperazinylcarbonyl) pentyl group, 6- (3-piperazinylcarbonyl) hexyl group, 4-tert-butoxycarbonyl-1-piperazinylcarbonylmethyl group, 2- ( 4-tert-butoxycarbonyl-1-piperazinylcarbonyl) ethyl group, 3- (4-tert-butoxycarbonyl-1-piperazinylcarbonyl) propyl group, 4- (4-tert-butoxycarbonyl-1-pipete) Razinylcarbonyl) butyl group, 5- (methoxycarbonyl-1-piperazinylcarbonyl) pentyl group, 6- (4-tert-butoxycarbonyl-1-piperazinylcarbonyl) hexyl group, 4-ethoxycarbonyl-1-yl Piperazinylcarbonylmethyl group, 2- (4-ethoxycarbonyl-1-pipera) Nylcarbonyl) ethyl group, 3- (4-n-propoxycarbonyl-1-piperazinylcarbonyl) propyl group, 4- (4-ethoxycarbonyl-1-piperazinylcarbonyl) butyl group, 5- (4-n) -Pentyloxycarbonyl-1-piperazinylcarbonyl) pentyl group, 6- (4-n-hexyloxycarbonyl-1-piperazinylcarbonyl) hexyl group, 4- (benzyloxycarbonyl) -1-piperazinylcarbonyl Methyl group, 2- (4- (benzyloxycarbonyl) -1-piperazinylcarbonyl) ethyl group, 3- (4- (benzyloxycarbonyl) -1-piperazinylcarbonyl) propyl group, 4- (4- (4- (benzyloxycarbonyl) -1-piperazinylcarbonyl) propyl group; (Benzyloxycarbonyl) -1-piperazinylcarbonyl) butyl group, 5- (4- (benzyloxycar) Bonyl) -1-piperazinylcarbonyl) pentyl group, 6- (4- (benzyloxycarbonyl) -1-piperazinylcarbonyl) hexyl group, 4- (4-methylbenzyloxycarbonyl) -1-piperazinyl Carbonylmethyl group, 4- (2,4-dimethylbenzyloxycarbonyl) -1-piperazinylcarbonylmethyl group, 4- (2,4,6-trimethylbenzyloxycarbonyl) -1-piperazinylcarbonylmethyl group, 4- (4-trifluoromethylbenzyloxycarbonyl) -1-piperazinylcarbonylmethyl group, 2- (4- (3,5-ditrifluoromethylbenzyloxycarbonyl) -1-piperazinylcarbonyl) ethyl group, 3- (4- (4-trifluoromethylbenzyloxycarbonyl) -1-piperazinyl radical Bonyl) propyl group, 4- (4- (4-trifluoromethylbenzyloxycarbonyl) -1-piperazinylcarbonyl) butyl group, 5- (4- (4-trifluoromethylbenzyloxycarbonyl) -1-pipe Razinylcarbonyl) pentyl group, 6- (4- (4-trifluoromethylbenzyloxycarbonyl) -1-piperazinylcarbonyl) hexyl group, 4- (2-phenylethoxycarbonyl) -1-piperazinylcarbonylmethyl Group, 2- {4- [2- (4-trifluoromethylphenyl) ethoxycarbonyl] -1-piperazinylcarbonyl} ethyl group, 3- {4- [2- (4-trifluoromethylphenyl) ethoxycarbonyl] -1-piperazinylcarbonyl} propyl group, 4- {4- [2- (4-trifluoromethyl) group Nyl) ethoxycarbonyl] -1-piperazinylcarbonyl} butyl group, 5- {4- [2- (2,4,6-trimethylphenyl) ethoxycarbonyl] -1-piperazinylcarbonyl} pentyl group, 6- {4- [2- (4-Trifluoromethylphenyl) ethoxycarbonyl] -1-piperazinylcarbonyl} hexyl group, 4-benzyl-1-piperazinylcarbonylmethyl group, 4- (4-trifluoromethylbenzyl) ) -1-Piperazinylcarbonylmethyl group, 2- (4- (4-trifluoromethylbenzyl) -1-piperazinylcarbonyl) ethyl group, 3- (4- (4-trifluoromethylbenzyl) -1 -Piperazinylcarbonyl) propyl group, 4- (4-methylbenzyl) -1-piperazinylcarbonylmethyl group, 4- (2,4-dialkyl) Methylbenzyl) -1-piperazinylcarbonylmethyl group, 4- (2,4,6-trimethylbenzyl) -1-piperazinylcarbonylmethyl group, 4- (4- (4-trifluoromethylbenzyl) -1 -Piperazinylcarbonyl) butyl group, 5- (4- (3,5-ditrifluoromethylbenzyl) -1-piperazinylcarbonyl) pentyl group, 6- (4- (4-trifluoromethylbenzyl) -1 -Piperazinylcarbonyl) hexyl group, 4- (4-biphenylylmethyl) -1-piperazinylcarbonylmethyl group, 2- (4- (4-biphenylylmethyl) -1-piperazinylcarbonyl) ethyl group , 3- (4- (4-biphenylylmethyl) -1-piperazinylcarbonyl) propyl group, 4- (4- (4-biphenylylmethyl) -1-piperazini Carbonyl) butyl group, 5- (4- (4-biphenylylmethyl) -1-piperazinylcarbonyl) pentyl group, 6- (4- (4-biphenylylmethyl) -1-piperazinylcarbonyl) hexyl group 2,4-dibenzyl-1-piperazinylcarbonylmethyl group, 4-benzyloxycarbonyl-3-benzyl-1-piperazinylcarbonylmethyl group, 4-ethoxycarbonyl-2,6-dibenzyl-1-piperazini Piperazinylcarbonyl C.sub.1-6 alkyl group (such as a C.sub.1-6 alkoxycarbonyl group on a piperazine ring, and a halogen-substituted or unsubstituted C.sub.1-6 alkyl group as a substituent group on a phenyl ring). Three optionally substituted phenyl C1-6 alkoxycarbonyl groups and halogens as substituents on the phenyl ring A group selected from the group consisting of a phenyl C1-6 alkyl group which may have 1 to 3 groups selected from the group consisting of a substituted or unsubstituted C1-6 alkyl group and a phenyl group is substituted by 1 to 3 groups May be mentioned).

  Examples of the phenylcarbamoyl C1-6 alkyl group (wherein at least one halogen-substituted or unsubstituted C1-6 alkyl group may be substituted on the phenyl ring) include, for example, 4-methylphenylcarbamoylmethyl group, 2 4, 4-Dimethylphenylcarbamoylmethyl group, 2,4, 6-trimethylphenylcarbamoylmethyl group, 3-ethylphenylcarbamoylmethyl group, 2-n-propylphenylcarbamoylmethyl group, 4-n-butylphenylcarbamoylmethyl group, 4 -N-pentylphenylcarbamoylmethyl group, 4-n-hexylphenylcarbamoylmethyl group, 4-trifluoromethylphenylcarbamoylmethyl group, 2- (4-trifluoromethylphenylcarbamoyl) ethyl group, 3- (3,5-) Ditrifluoromethyl Phenyl such as nylcarbamoyl) propyl group, 4- (4-trifluoromethylphenylcarbamoyl) butyl group, 5- (4-trifluoromethylphenylcarbamoyl) pentyl group, 6- (4-trifluoromethylphenylcarbamoyl) hexyl group, etc. Mention may be made of a phenylcarbamoyl C1-6 alkyl group which may have 1 to 3 halogen-substituted or unsubstituted C1-6 alkyl groups as a substituent on the ring.

  Examples of the benzoxazolyl C1-6 alkyl group (wherein at least one oxo group may be substituted on the benzoxazole ring) include, for example, benzoxazol-2-ylmethyl group and benzoxazole-4- Ylmethyl group, benzoxazol-5-ylmethyl group, benzoxazol-6-ylmethyl group, benzoxazol-7-ylmethyl group, 2- (benzoxazol-2-yl) ethyl group, 1- (benzoxazol-4-yl) group Ethyl group, 3- (benzoxazol-5-yl) propyl group, 4- (benzoxazol-6-yl) butyl group, 5- (benzoxazol-7-yl) pentyl group, 6- (benzoxazole-2-yl) group 1) hexyl group, 2-methyl-3- (benzoxazol-4-yl) propyl group, 1 1-dimethyl-2- (benzoxazol-5-yl) ethyl group, (2,3-dihydro-2-oxo-benzoxazol-3-yl) methyl group, (2,3-dihydro-2-oxo-benzo) Oxazol-4-yl) methyl group, (2,3-dihydro-2-oxo-benzoxazol-5-yl) methyl group, (2,3-dihydro-2-oxo-benzoxazol-6-yl) methyl group And (2,3-dihydro-2-oxo-benzoxazol-7-yl) methyl group etc. can be mentioned.

  Examples of the phenylthiocarbamoyl group (wherein at least one halogen atom may be substituted on the phenyl ring) include, for example, phenylthiocarbamoyl group, 4-fluorophenylthiocarbamoyl group, 4-chlorophenylthiocarbamoyl group, Phenyl ring such as 4-bromophenylthiocarbamoyl group, 3,4-dichlorophenylthiocarbamoyl group, 3,4,6-trichlorophenylthiocarbamoyl group, 2,3,4,5,6-pentafluorophenylthiocarbamoyl group, etc. And a phenylthiocarbamoyl group which may be substituted by 1 to 5 halogens as a substituent.

  As C 1-8 alkoxycarbonyl group, for example, methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, n-pentyloxycarbonyl group, n-hexyloxycarbonyl group, n-heptyloxycarbonyl group, n-octyl An oxycarbonyl group etc. can be mentioned.

  A phenyl C1-6 alkoxycarbonyl group (a halogen atom, a C1-6 alkoxycarbonyl group on a phenyl ring, an amino group optionally having a C1-6 alkoxycarbonyl group as a substituent, a halogen-substituted or unsubstituted C1 As at least one member selected from the group consisting of a -6 alkyl group, a halogen-substituted or unsubstituted C1-6 alkoxy group, a nitro group and a C1-6 alkylthio group, for example, Benzyloxycarbonyl group, 1-phenethyloxycarbonyl group, 2-phenethyloxycarbonyl group, 3-phenylpropoxycarbonyl group, 2-phenylpropoxycarbonyl group, 4-phenylbutoxycarbonyl group, 5-phenylpentyloxycarbonyl group, 4 -Phenyl pentyl oxycarbonyl 6-phenylhexyloxycarbonyl group, 2-fluorobenzyloxycarbonyl group, 3-fluorobenzyloxycarbonyl group, 4-fluorobenzyloxycarbonyl group, 2-chlorobenzyloxycarbonyl group, 3-chlorobenzyloxycarbonyl group, 4 -Chlorobenzyloxycarbonyl group, 2-bromobenzyloxycarbonyl group, 3-bromobenzyloxycarbonyl group, 4-bromobenzyloxycarbonyl group, 2-iodobenzyloxycarbonyl group, 3-iodobenzyloxycarbonyl group, 4-iodo Benzyloxycarbonyl group, 2,3-difluorobenzyloxycarbonyl group, 3,4-difluorobenzyloxycarbonyl group, 3,5-difluorobenzyloxycarbonyl group, 2,4-difluoroben Roxycarbonyl, 2,6-difluorobenzyloxycarbonyl, 2,4,6-trifluorobenzyloxycarbonyl, 2,3,4,5,6-pentafluorobenzyloxycarbonyl, 3,4,5 -Trifluorobenzyloxycarbonyl group, 2,3-dichlorobenzyloxycarbonyl group, 3,4-dichlorobenzyloxycarbonyl group, 3,5-dichlorobenzyloxycarbonyl group, 2,4-dichlorobenzyloxycarbonyl group, 2, 6-dichlorobenzyloxycarbonyl group, 2,4,6-trichlorobenzyloxycarbonyl group, 3,4,5-trichlorobenzyloxycarbonyl group, 2-trifluoromethylbenzyloxycarbonyl group, 3-methylbenzyloxycarbonyl group, 2,4-dimethylbenzyl Oxycarbonyl group, 2,4,6-trimethylbenzyloxycarbonyl group, 3-difluoromethylbenzyloxycarbonyl group, 4-difluoromethylbenzyloxycarbonyl group, 4-chloro-3-difluoromethylbenzyloxycarbonyl group, 3-chloro -4-difluoromethylbenzyloxycarbonyl group, 3-bromo-4-difluoromethylbenzyloxycarbonyl group, 3,5-difluoro-4-difluoromethylbenzyloxycarbonyl group, 3,5-ditrifluoromethylbenzyloxycarbonyl group, 3-trifluoromethylbenzyloxycarbonyl group, 4-trifluoromethylbenzyloxycarbonyl group, 4-fluoro-3-trifluoromethylbenzyloxycarbonyl group, 3-fluoro-4-trifluoromethane Benzyloxycarbonyl group, 2-pentafluoroethyl benzyloxycarbonyl group, 4-chloro-3-pentafluoroethyl benzyloxycarbonyl group, 3-chloro-4-pentafluoroethyl benzyloxycarbonyl group, 2-pentafluoroethyl benzyl group Oxycarbonyl group, 3-pentafluoroethyl benzyloxycarbonyl group, 4-pentafluoroethyl benzyloxycarbonyl group, 3-methoxybenzyloxycarbonyl group, 2,4-dimethoxybenzyloxycarbonyl group, 2,4,6-trimethoxy Benzyloxycarbonyl group, 2-trifluoromethoxybenzyloxycarbonyl group, 3-trifluoromethoxybenzyloxycarbonyl group, 4-trifluoromethoxybenzyloxycarbonyl group, 4- Luoro-3-trifluoromethoxybenzyloxycarbonyl group, 3-fluoro-4-trifluoromethoxybenzyloxycarbonyl group, 2-pentafluoroethoxybenzyloxycarbonyl group, 3-pentafluoroethoxybenzyloxycarbonyl group, 4-pentafluoro Ethoxybenzyloxycarbonyl group, 3-chloro-4-trifluoromethoxybenzyloxycarbonyl group, 3-chloro-4-pentafluoroethoxybenzyloxycarbonyl group, 2- (2-trifluoromethylphenyl) ethoxycarbonyl group, 2- (3-trifluoromethylphenyl) ethoxycarbonyl group, 2- (4-trifluoromethylphenyl) ethoxycarbonyl group, 2- (4-trifluoromethoxyphenyl) ethoxycarbonyl group, 2- ( 2-pentafluoroethoxyphenyl) ethoxycarbonyl group, 2- (3-pentafluoroethoxyphenyl) ethoxycarbonyl group, 2- (4-pentafluoroethoxyphenyl) ethoxycarbonyl group, 3- (2-trifluoromethylphenyl) propoxy Carbonyl group, 3- (3-trifluoromethylphenyl) propoxycarbonyl group, 3- (4-trifluoromethylphenyl) propoxycarbonyl group, 3- (2-trifluoromethylphenyl) propoxycarbonyl group, 3- (3- Trifluoromethoxyphenyl) propoxycarbonyl group, 3- (4-trifluoromethoxyphenyl) propoxycarbonyl group, 3- (3-pentafluoroethoxyphenyl) propoxycarbonyl group, 3- (4-pentafluoroethoxyphenyl) ) Propoxycarbonyl group, 4- (3-pentafluoroethoxyphenyl) butoxycarbonyl group, 5- (4-trifluoromethylphenyl) pentyloxycarbonyl group, 4- (4-trifluoromethylphenyl) pentyloxycarbonyl group, 4) -(4-Trifluoromethoxyphenyl) pentyloxycarbonyl group, 6- (3-trifluoromethylphenyl) hexyloxycarbonyl group, 6- (4-trifluoromethylphenyl) hexyloxycarbonyl group, 6- (4-trichlorophenyl) hexyloxycarbonyl group Fluoromethoxyphenyl) hexyloxycarbonyl group, 2-methylthiobenzyloxycarbonyl group, 3-methylthiobenzyloxycarbonyl group, 4-methylthiobenzyloxycarbonyl group, 2- (2-methylthiophenyl) ethoxycarbonyl , 2- (3-methylthiophenyl) ethoxycarbonyl group, 2- (4-methylthiophenyl) ethoxycarbonyl group, 3- (4-methylthiophenyl) propoxycarbonyl group, 4- (4-methylthiophenyl) butoxycarbonyl group, 5 -(4-Methylthiophenyl) pentyloxycarbonyl group, 6- (4-methylthiophenyl) hexyloxycarbonyl group, 2-methoxycarbonylbenzyloxycarbonyl group, 3-methoxycarbonylbenzyloxycarbonyl group, 4-methoxycarbonylbenzyloxycarbonyl Group, 2- (2-methoxycarbonylphenyl) ethoxycarbonyl group, 2- (3-methoxycarbonylphenyl) ethoxycarbonyl group, 2- (4-methoxycarbonylphenyl) ethoxycarbonyl group, 3- (4 -Methoxycarbonylphenyl) propoxycarbonyl group, 4- (4-methoxycarbonylphenyl) butoxycarbonyl group, 5- (4-methoxycarbonylphenyl) pentyloxycarbonyl group, 6- (4-methoxycarbonylphenyl) hexyloxycarbonyl group, 4-n-pentyloxycarbonylaminobenzyloxycarbonyl group, 4-ethoxycarbonylaminobenzyloxycarbonyl group, 4-propoxycarbonylaminobenzyloxycarbonyl group, 4-tert-butoxycarbonylaminobenzyloxycarbonyl group, 2- (n- Hexyloxycarbonylaminophenyl) ethoxycarbonyl group, 3- (4-tert-butoxycarbonylaminophenyl) propoxycarbonyl group, 4- (4-tert-buto) Sylcoylaminophenyl) butoxycarbonyl group, 5- (4-tert-butoxycarbonylaminophenyl) pentyloxycarbonyl group, 6- (4-tert-butoxycarbonylaminophenyl) hexyloxycarbonyl group, 2-nitrobenzyloxycarbonyl group , 3-nitrobenzyloxycarbonyl group, 4-nitrobenzyloxycarbonyl group, 2- (2-nitrophenyl) ethoxycarbonyl group, 2- (3-nitrophenyl) ethoxycarbonyl group, 2- (4-nitrophenyl) ethoxy Carbonyl group, 3- (2,4-dinitrophenyl) propoxycarbonyl group, 4- (4-nitrophenyl) butoxycarbonyl group, 5- (4-nitrophenyl) pentyloxycarbonyl group, 6- (2,4,6 -Trinitropheny ) Hexyloxycarbonyl group, 2-aminobenzyloxycarbonyl group, 3-aminobenzyloxycarbonyl group, 4-aminobenzyloxycarbonyl group, 2- (2-aminophenyl) ethoxycarbonyl group, 2- (2,3-diamino) Phenyl) ethoxycarbonyl group, 2- (4-aminophenyl) ethoxycarbonyl group, 3- (2,4,6-triaminophenyl) propoxycarbonyl group, 4- (4-aminophenyl) butoxycarbonyl group, 5- (4) 4-aminophenyl) pentyloxycarbonyl group, 6- (4-aminophenyl) hexyloxycarbonyl group, 2-ethoxycarbonylbenzyloxycarbonyl group, 3-ethoxycarbonylbenzyloxycarbonyl group, 4-methoxycarbonylbenzyloxycarbonyl group, 2- (2-ethoxycarbonylphenyl) ethoxycarbonyl group, 2- (3-ethoxycarbonylphenyl) ethoxycarbonyl group, 2- (4-ethoxycarbonylphenyl) ethoxycarbonyl group, 3- (4-n-butoxycarbonylphenyl) propoxycarbonyl Group, 4- (4-n-pentyloxycarbonylphenyl) butoxycarbonyl group, 5- (4-n-hexyloxycarbonylphenyl) pentyloxycarbonyl group, 6- (4-ethoxycarbonylphenyl) hexyloxycarbonyl group, etc. A phenyl C1-6 alkoxycarbonyl group (on the phenyl ring, a halogen atom, a C1-6 alkoxycarbonyl group, an amino group which may have a C1-6 alkoxycarbonyl group as a substituent, a halogen-substituted or unsubstituted C1 ~ 6 1 to 5, preferably 1 to 3 groups selected from the group consisting of an alkyl group, a halogen substituted or unsubstituted C1-6 alkoxy group, a nitro group and a C1-6 alkylthio group) Can be mentioned.

  Examples of the benzhydryloxycarbonyl group (in which at least one halogen atom may be substituted on the phenyl ring) include, for example, benzhydryloxycarbonyl group, 3-fluorobenzhydryloxycarbonyl group, 4 -Fluorobenzhydryloxycarbonyl group, 3,3'-difluorobenzhydryloxycarbonyl group, 3,4'-difluorobenzhydryloxycarbonyl group, 4,4'-difluorobenzhydryloxycarbonyl group, 3, 4,4'-Trifluorobenzhydryloxycarbonyl group, 3,3 ', 4,4'-tetrafluorobenzhydryloxycarbonyl group, 2,2', 4,4'-tetrafluorobenzhydryloxycarbonyl Group, 3,3 ', 5,5'-tetrafluorobenzhydryloxy carboni Group, 3-chlorobenzhydryloxycarbonyl group, 4-chlorobenzhydryloxycarbonyl group, 3,3'-dichlorobenzhydryloxycarbonyl group, 3,4'-dichlorobenzhydryloxycarbonyl group, 4, 4'-Dichlorobenzhydryloxycarbonyl group, 3,4,4'-trichlorobenzhydryloxycarbonyl group, 3,3 ', 4,4'-tetrachlorobenzhydryloxycarbonyl group, 2,2', Benzhydryloxycarbonyl groups such as 4,4'-tetrachlorobenzhydryloxycarbonyl group, 3,3 ', 5,5'-tetrachlorobenzhydryloxycarbonyl group (one halogen atom on the phenyl ring To 4 may be substituted).

  As a phenyl substituted or unsubstituted phenyl C1-6 alkoxycarbonyl group, for example, benzyloxycarbonyl group, 1-phenylethoxycarbonyl group, 2-phenylethoxycarbonyl group, 3-phenylpropoxycarbonyl group, 2-phenylpropoxycarbonyl group , 4-phenylbutoxycarbonyl group, 5-phenylpentoxy carbonyl group, 4-phenyl pentoxy carbonyl group, 6-phenylhexyloxycarbonyl group, 2-biphenylyl methoxycarbonyl group, 2- (2-biphenylyl) ethoxycarbonyl group , 3- (2-biphenylyl) propoxycarbonyl group, 4- (2-biphenylyl) butoxycarbonyl group, 5- (2-biphenylyl) pentoxy carbonyl group, 6- (2-biphenylyl) hexyloxycar Group, 3-biphenylyl methoxycarbonyl group, 2- (3-biphenylyl) ethoxycarbonyl group, 3- (3-biphenylyl) propoxycarbonyl group, 4- (3-biphenylyl) butoxycarbonyl group, 5- (3-biphenylyl group ) Pentoxy carbonyl group, 6- (3-biphenylyl) hexyloxycarbonyl group, 4-biphenylyl methoxycarbonyl group, 2- (4-biphenylyl) ethoxycarbonyl group, 3- (4-biphenylyl) propoxycarbonyl group, 4- Examples include (4-biphenylyl) butoxycarbonyl group, 5- (4-biphenylyl) pentoxy carbonyl group, 6- (4-biphenylyl) hexyloxycarbonyl group and the like.

  As a pyridyl C1-6 alkoxy carbonyl group, for example, 2- pyridyl methoxy carbonyl group, 3- pyridyl methoxy carbonyl group, 4- pyridyl methoxy carbonyl group, 2- (2- pyridyl) ethoxy carbonyl group, 2- (3- pyridyl) group )) Ethoxycarbonyl group, 2- (4-pyridyl) ethoxycarbonyl group, 3- (2-pyridyl) propoxycarbonyl group, 3- (3-pyridyl) propoxycarbonyl group, 3- (4-pyridyl) propoxycarbonyl group, 4) -(2-pyridyl) butoxycarbonyl group, 4- (3-pyridyl) butoxycarbonyl group, 4- (4-pyridyl) butoxycarbonyl group, 5- (2-pyridyl) pentyloxycarbonyl group, 5- (3-pyridyl) group ) Pentyloxycarbonyl group, 5- (4-pyridyl) pentyl Alkoxycarbonyl group, 6- (2-pyridyl) hexyloxy group, 6- (3-pyridyl) hexyloxy group, 6- (4-pyridyl) and a hexyl oxycarbonyl group.

  As the C1-6 alkoxy substituted C1-6 alkoxycarbonyl group, for example, methoxy methoxycarbonyl group, 2-methoxy ethoxy carbonyl group, ethoxy methoxy carbonyl group, n-propoxy methoxy carbonyl group, n-butoxy methoxy carbonyl group, n-pentyl Oxymethoxycarbonyl group, n-hexyloxymethoxycarbonyl group, 1-methoxyethoxycarbonyl group, 2-ethoxyethoxycarbonyl group, 2-n-propoxyethoxycarbonyl group, n-butoxymethoxycarbonyl group, n-pentyloxymethoxycarbonyl group , N-hexyloxymethoxycarbonyl group, 3-methoxypropoxycarbonyl group, 4-methoxybutoxycarbonyl group, 5-methoxypentyloxycarbonyl group, 6-methoxyhexylo group A xycarbonyl group etc. can be mentioned.

  From a piperazinyl C.sub.1-6 alkoxycarbonyl group (C.sub.1-6 alkoxycarbonyl group and phenyl C.sub.1-6 alkoxycarbonyl group on the piperazine ring [at least one halogen atom may be substituted on the phenyl ring]) As at least one group selected from the group consisting of: — (1-piperazinyl) methoxycarbonyl group, 2- (2-piperazinyl) ethoxycarbonyl group, 1- (3-piperazinyl); ) Ethoxycarbonyl group, 3- (4-piperazinyl) propoxycarbonyl group, 4- (1-piperazinyl butoxycarbonyl group, 5- (2-piperazinyl) pentyloxycarbonyl group, 6- (3-piperazinyl) hexyloxycarbonyl group Group, 2-methyl-3- (1-piperazinyl) propoxycal Group, 1,1-dimethyl-2- (4-piperazinyl) ethoxycarbonyl group, 2- (1-piperazinyl) ethoxycarbonyl group, 2- (4-methoxycarbonyl-1-piperazinyl) ethoxycarbonyl group, 2- ( 4-ethoxycarbonyl-1-piperazinyl) ethoxycarbonyl group, 2- (4-n-propoxycarbonyl-1-piperazinyl) ethoxycarbonyl group, 2- (4-tert-butoxycarbonyl-1-piperazinyl) ethoxycarbonyl group, 2 -(4-sec-butoxycarbonyl-1-piperazinyl) ethoxycarbonyl group, 2- (4-n-pentyloxycarbonyl-1-piperazinyl) ethoxycarbonyl group, 2- (4-n-hexyloxycarbonyl-1-piperazinyl) ) Ethoxycarbonyl group, 2- (4-be Dyloxycarbonyl-1-piperazinyl) ethoxycarbonyl group, 2- (4-phenylethoxycarbonyl-1-piperazinyl) ethoxycarbonyl group, 2- (4- (3-phenylpropoxycarbonyl) -1-piperazinyl) ethoxycarbonyl group, 2- (4- (2-fluorobenzyloxycarbonyl) -1-piperazinyl) ethoxycarbonyl group, 2- (4- (4-fluorobenzyloxycarbonyl) -1-piperazinyl) ethoxycarbonyl group, 2- (4- (4- (4-fluorobenzyloxycarbonyl)) 4-chlorobenzyloxycarbonyl) -1-piperazinyl) ethoxycarbonyl group, 2- (4- (3-chlorobenzyloxycarbonyl) -1-piperazinyl) ethoxycarbonyl group, 2- (4- (2-bromobenzyloxycarbonyl) group )-1-Piperazinyl) Etoki A carbonyl group, 2- (4- (2-chlorobenzyloxycarbonyl) -1-piperazinyl) ethoxycarbonyl group, 2- (4- (3,4-difluorobenzyloxycarbonyl) -1-piperazinyl) ethoxycarbonyl group, 2- (4- (2,3,4,5,6-pentafluorobenzyloxycarbonyl) -1-piperazinyl) methoxycarbonyl group, 2- (4- (2,4-dichlorobenzyloxycarbonyl) -1-piperazinyl ) Ethoxycarbonyl group, 2- (4- (2,4,6-trichlorobenzyloxycarbonyl) -1-piperazinyl) ethoxycarbonyl group, (3,4-methoxycarbonyl-1-piperazinyl) methoxycarbonyl group, (2, 5-Methoxycarbonyl-4-benzyloxycarbonyl-1-piperazinyl) group Piperazinyl C1-6 alkoxycarbonyl group such as xycarbonyl group (C1-6 alkoxycarbonyl group as a substituent, and phenyl C1 having 1 to 5 halogen atoms as a substituent on phenyl ring as a substituent One to three groups selected from the group consisting of 6 alkoxycarbonyl groups may be substituted. Can be mentioned.

  Examples of the phenoxycarbonyl group (on the phenyl ring, at least one member selected from the group consisting of a C1-6 alkyl group and a C1-6 alkoxy group may be substituted) include, for example, a phenoxy carbonyl group, 2-methylphenoxycarbonyl group, 3-methylphenoxycarbonyl group, 4-methylphenoxycarbonyl group, 2-ethylphenoxycarbonyl group, 3-ethyl cyphenoxycarbonyl group, 4-ethylphenoxycarbonyl group, 4-propylphenoxycarbonyl group, 4-tert-butylphenoxycarbonyl group, 4-butylphenoxycarbonyl group, 2,3-dimethylphenoxycarbonyl group, 3,4,5-trimethylphenoxycarbonyl group, 4-pentylphenoxycarbonyl group, 4-hexylphenoxycarbonyl group 2-methoxyphenoxycarbonyl group, 3-methoxyphenoxycarbonyl group, 4-methoxyphenoxycarbonyl group, 2-ethoxyphenoxycarbonyl group, 3-ethoxyphenoxycarbonyl group, 4-ethoxyphenoxycarbonyl group, 4-propoxyphenoxycarbonyl group, 4 -Tert-butoxyphenoxycarbonyl group, 4-n-butoxyphenoxycarbonyl group, 2,3-dimethoxyphenoxycarbonyl group, 3,4,5-trimethoxyphenoxycarbonyl group, 4-pentoxyphenoxycarbonyl group, 4-hexyloxy Phenoxycarbonyl groups such as phenoxycarbonyl group, 2-methyl-4-methoxyphenoxycarbonyl group (on the phenyl ring, selected from the group consisting of C1-6 alkyl group and C1-6 alkoxy group Group can be exemplified also may) have been 1-3 substituents.

  Examples of benzoyl group (on the phenyl ring, at least one halogen-substituted or unsubstituted C1-6 alkyl group may be substituted) include, for example, benzoyl group, 2-methylbenzoyl group, 3-methylbenzoyl group , 4-Methylbenzoyl, 4-ethylbenzoyl, 4-n-propylbenzoyl, 4-tert-butylbenzoyl, 4-n-pentylbenzoyl, 4-n-hexylbenzoyl, 2,3-dimethyl Benzoyl group, 3,4-dimethyl benzoyl group, 2,4,6-trimethyl benzoyl group, 2-trifluoromethyl benzoyl group, 3-trifluoromethyl benzoyl group, 4-trifluoromethyl benzoyl group, 4-pentafluoroethyl Benzoyl group, 2,3-ditrifluoromethylbenzoyl group, 3,4-ditrif (On the phenyl ring, a halogen substituted or C1~6 alkyl group unsubstituted may be 1-3 substituents) Oro methylbenzoyl benzoyl group such as and the like.

  Examples of the phenyl C2-6 alkanoyl group (wherein at least one halogen-substituted or unsubstituted C1-6 alkyl group may be substituted on the phenyl ring) include, for example, phenylacetyl group, 3-phenylpropionyl group, 4-phenylbutyryl group, 5-phenylpentanoyl group, 6-phenylhexanoyl group, 2-methylphenylacetyl group, 3-methylphenylacetyl group, 4-methylphenylacetyl group, 2-trifluoromethylphenylacetyl group , 3-trifluoromethylphenylacetyl group, 4-trifluoromethylphenylacetyl group, 3- (2,4-dimethylphenyl) propionyl group, (2,4,6-trimethylphenyl) acetyl group, 3- (2- (2-) Methylphenyl) propionyl group, 3- (3-methylphenyl) propioni group Group, 3- (4-methylphenyl) propionyl group, 3- (2-trifluoromethylphenyl) propionyl group, 3- (3-trifluoromethylphenyl) propionyl group, 3- (4-trifluoromethylphenyl) propionyl Group, 3- (3,5-dimethylphenyl) propionyl group, 4- (4-trifluoromethylphenyl) butyryl group, 5- (4-trifluoromethylphenyl) pentanoyl group, 6- (3,5-ditrifluoro) Phenyl C2-6 such as methylphenyl) hexanoyl group, 4- (4-trifluoromethylphenyl) butyryl group, 5- (4-pentafluoroethylphenyl) pentanoyl group, 6- (4-pentafluoroethylphenyl) hexanoyl group, etc. Alkanoyl group (on the phenyl ring, substituted or unsubstituted C 6 alkyl group can be exemplified also may) have been 1-3 substituents.

  Examples of phenoxy C2-6 alkanoyl group (1 to 3 halogen atoms may be substituted on the phenyl ring) include, for example, phenoxyacetyl group, 3-phenoxypropionyl group, 4-phenoxybutyryl group, 5 -Phenoxypentanoyl group, 6-phenoxyhexanoyl group, 4- (4-chlorophenoxy) butyryl group, 5- (4-chlorophenoxy) pentanoyl group, 6- (4-chlorophenoxy) hexanoyl group, 2-fluorophenoxy Acetyl group, 3-fluorophenoxyacetyl group, 4-fluorophenoxyacetyl group, 2-chlorophenoxyacetyl group, 3-chlorophenoxyacetyl group, 4-chlorophenoxyacetyl group, 4-bromophenoxyacetyl group, 2,3-difluoro Phenoxyacetyl group, 2-fluoro-4- Rolophenoxyacetyl group, 3,5-difluorophenoxyacetyl group, 2,4,6-trichlorophenoxyacetyl group, 3- (2-fluorophenoxy) propionyl group, 3- (3-fluorophenoxy) propionyl group, 3- (3- 4-fluorophenoxy) propionyl group, 3- (2-chlorophenoxy) propionyl group, 3- (3-chlorophenoxy) propionyl group, 3- (4-chlorophenoxy) propionyl group, 3- (4-bromophenoxy) propionyl Group, 3- (2,3-difluorophenoxy) propionyl group, 3- (2-fluoro-4-chlorophenoxy) propionyl group, 3- (3,5-difluorophenoxy) propionyl group, 4- (4-fluorophenoxy) group ) Butyryl group, 5- (4-bromophenoxy) pentano And 6- (4-chlorophenoxy) hexanoyl, 4- (4-chlorophenoxy) butyryl, 5- (4-iodophenoxy) pentanoyl, 6- (4-chlorophenoxy) hexanoyl and the like. Can.

Piperazinyl C2-6 alkanoyl group (in the piperazine ring, a C1-6 alkanoyl group, a phenyl C1-6 alkyl group [in the phenyl ring, a phenyl group, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and At least one group selected from the group consisting of halogen substituted or unsubstituted C1-6 alkoxy group may be substituted], phenyl C1-6 alkoxycarbonyl group [a halogen atom on a phenyl ring, halogen At least one group may be substituted with a group selected from the group consisting of a substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group], phenylcarbamoyl C1-6 alkyl group [On the phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group And at least one group selected from the group consisting of halogen-substituted or unsubstituted C.sub.1-6 alkoxy groups may be substituted], phenylcarbamoyl group [in the case of a phenyl ring, a halogen atom, a halogen-substituted or an unsubstituted group; At least one group selected from the group consisting of a substituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group may be substituted] and a group consisting of a benzoxazolyl group As at least one kind of the substituted groups) may be, for example, 1-piperazinylacetyl group, 3- (2-piperazinyl) propanoyl group, 4- (3-piperazinyl) butyryl group, 4- (4-piperazinyl) pentanoyl group, 5- (1-piperazinyl) pentanoyl group, 6- (2-piperazinyl) hexanoyl group, 4-amino Tyl-1-piperazinylacetyl group, 3- (4-propionyl-1-piperazinyl) propionyl group, 3- (4-butyryl-1-piperazinyl) butyryl group, 4- (4-pentanoyl-1-piperazinyl) butyryl group Group, 5- (4-hexanoyl-1-piperazinyl) pentanoyl group, 6- (4-acetyl-1-piperazinyl) hexanoyl group, 4-benzyl-1-piperazinyl acetyl group, 3- [4- (2- (2-) Phenylethyl) -1-piperazinyl] propionyl group, (4-acetyl-3-benzyl-1-piperazinyl) acetyl group, (4-benzyloxycarbonyl-2-benzyl-1-piperazinyl) acetyl group, (4-phenylcarbamoyl) -2,6-Dibenzyl-1-piperazinyl) acetyl group, 4- [4- (1-phenylethyl)- 1-piperazinyl! Butyryl group, [4- (3-phenylpropyl) 1-piperazinyl] butyryl group, 5- [4- (5-phenylpentyl) -1-piperazinyl] pentanoyl group, 6- [4- (6- (6-phenyl)] Phenylhexyl) -1-piperazinyl] hexanoyl group, 4- (4-phenylbenzyl) -1-piperazinylacetyl group, 3- [4- (3-fluorobenzyl) -1-piperazinyl] propionyl group, 4- [4 4- (2,3,4,5,6-pentafluorobenzyl) -1-piperazinyl] butyryl group, 4- [4- (2,4-dichlorobenzyl) -1-piperazinyl] butyryl group, 5- [4 -(2,4,6-trichlorobenzyl) -1-piperazinyl] pentanoyl group, 6- [4- (4-methylbenzyl) -1-piperazinyl] hexanoyl group, 4- (4-trifluoromethylbenzyl) -1-piperazinyl] acetyl group, [4- (3,5-ditrifluoromethylbenzyl) -1-piperazinyl] acetyl group, [4- (2,3-dimethylbenzyl)] -1-piperazinyl! Acetyl group, [4- (2,4,6-trimethylbenzyl) -1-piperazinyl] acetyl group, 6- [4- (4-methoxybenzyl) -1-piperazinyl] hexanoyl group, [4 -(4-Trifluoromethoxybenzyl) -1-piperazinyl] acetyl group, [4- (3,5-ditrifluoromethoxybenzyl) -1-piperazinyl] acetyl group, [4- (2,3-dimethoxybenzyl)- 1-piperazinyl] acetyl group, [4- (2,4,6-trimethoxybenzyl) -1-piperazinyl] acetyl group, 3- (4-ben Roxycarbonyl-1-piperazinyl) propionyl group, 4- (2,4-dichlorobenzyloxycarbonyl-1-piperazinyl) acetyl group, 3- (4-benzyloxycarbonyl-1-piperazinyl) butyryl group, 4- (4 -Benzyloxycarbonyl-1-piperazinyl) butyryl group, 5- (4-benzyloxycarbonyl-1-piperazinyl) pentanoyl group, 6- (4-benzyloxycarbonyl-1-piperazinyl) hexanoyl group, 3- (4- (4- (4-benzyloxycarbonyl-1-piperazinyl) hexanoyl group) 2-fluorobenzyloxycarbonyl) -1-piperazinyl) propionyl group, 3- (4- (2-fluorobenzyloxycarbonyl) -1-piperazinyl) butyryl group, 4- (4- (2-fluorobenzyloxycarbonyl)- 1-piperazinyl) butyryl group, 5- (4-) 2,3,4,5,6-pentafluorobenzyloxycarbonyl) -1-piperazinyl) pentanoyl group, 6- (4-fluorobenzyloxycarbonyl-1-piperazinyl) hexanoyl group, 3- (4- (2,3) -Difluorobenzyloxycarbonyl) -1-piperazinyl) butyryl group, 4- (4- (3-fluorobenzyloxycarbonyl) -1-piperazinyl) butyryl group, 5- (4- (3-fluorobenzyloxycarbonyl) -1 -Piperazinyl) pentanoyl group, 3- (4- (4-fluorobenzyloxycarbonyl) -1-piperazinyl) butyryl group, 4- (4- (4-fluorobenzyloxycarbonyl) -1-piperazinyl) butyryl group, 5- (4- (4-fluorobenzyloxycarbonyl) -1-piperazinyl) pipe Intanoyl group, 6- (4- (4-fluorobenzyloxycarbonyl) -1-piperazinyl) hexanoyl group, 3- (4- (2-chlorobenzyloxycarbonyl) -1-piperazinyl) propionyl group, 3- (4- (4-chlorochloro) (2-chlorobenzyloxycarbonyl) -1-piperazinyl) butyryl group, 4- (4- (2-chlorobenzyloxycarbonyl) -1-piperazinyl) butyryl group, 5- (4- (2-chlorobenzyloxycarbonyl) group -1-piperazinyl) pentanoyl group, 6- (2,4,6-trichlorobenzyloxycarbonyl-1-piperazinyl) hexanoyl group, 3- (4- (3-chlorobenzyloxycarbonyl) -1-piperazinyl) propionyl group, 3- (4- (3-Chlorobenzyloxycarbonyl) -1-piperazinyl Butyryl group, 4- (4- (3-chlorobenzyloxycarbonyl) -1-piperazinyl) butyryl group, 5- (4- (3-chlorobenzyloxycarbonyl) -1-piperazinyl) pentanoyl group, 6- (3- (3-chlorobenzyloxycarbonyl) -1-piperazinyl group Chlorobenzyloxycarbonyl-1-piperazinyl) hexanoyl group, 2- (4- (4-chlorobenzyloxycarbonyl) -1-piperazinyl) propionyl group, 3- (4- (4-chlorobenzyloxycarbonyl) -1-piperazinyl ) Butyryl group, 4- (4- (4-chlorobenzyloxycarbonyl) -1-piperazinyl) butyryl group, 5- (4- (4-chlorobenzyloxycarbonyl) -1-piperazinyl) pentanoyl group, 6- (4 -Chlorobenzyloxycarbonyl-1-piperazinyl) hexanoyl group, (4- ( -Methylbenzyloxycarbonyl) -1-piperazinyl) acetyl, (4- (2,4-dimethylbenzyloxycarbonyl) -1-piperazinyl) acetyl, (4- (2,4,6-trimethylbenzyloxycarbonyl) -1-piperazinyl) acetyl group, (4- (2-methoxybenzyloxycarbonyl) -1-piperazinyl) acetyl group, (4- (2,4-dimethoxybenzyloxycarbonyl) -1-piperazinyl) acetyl group, (4 -(2,4,6-trimethoxybenzyloxycarbonyl) -1-piperazinyl) acetyl group, 4- (3,5-ditrifluoromethylbenzyloxycarbonyl) -1-piperazinyl) acetyl group, 4- (3,5 -Ditrifluoromethoxybenzyloxycarbonyl) -1-piperazinyl) aceto Ethyl, 3- (4- (2-trifluoromethylbenzyloxycarbonyl) -1-piperazinyl) propionyl, 3- (4- (2-trifluoromethylbenzyloxycarbonyl) -1-piperazinyl) butyryl, 4 -(4- (2-trifluoromethylbenzyloxycarbonyl) -1-piperazinyl) butyryl group, 5- (4- (2-trifluoromethylbenzyloxycarbonyl) -1-piperazinyl) pentanoyl group, 6- (4- Trifluoromethylbenzyloxycarbonyl-1-piperazinyl) hexanoyl, 3- (4- (3-trifluoromethylbenzyloxycarbonyl) -1-piperazinyl) butyryl group, 4- (4- (3-trifluoromethylbenzyloxy) Carbonyl) -1-piperazinyl) butyryl group, 5- (4-) 3-trifluoromethylbenzyloxycarbonyl) -1-piperazinyl) pentanoyl group, 3- (4- (4-trifluoromethylbenzyloxycarbonyl) -1-piperazinyl) butyryl group, 4- (4- (4-trifluoro) Methylbenzyloxycarbonyl) -1-piperazinyl) butyryl group, 5- (4- (4-trifluoromethylbenzyloxycarbonyl) -1-piperazinyl) pentanoyl group, 6- (4- (4-trifluoromethylbenzyloxycarbonyl) group ) -1-Piperazinyl) hexanoyl group, 2- (4- (2-trifluoromethoxybenzyloxycarbonyl) -1-piperazinyl) propionyl group, 3- (4- (2-trifluoromethoxybenzyloxycarbonyl) -1-) Piperazinyl) butyryl group, 4- (4- (4- ( -Trifluoromethoxybenzyloxycarbonyl) -1-piperazinyl) butyryl group, 5- (4- (2-trifluoromethoxybenzyloxycarbonyl) -1-piperazinyl) pentanoyl group, 6- (4-trifluoromethoxybenzyloxycarbonyl) -1-piperazinyl) hexanoyl, 3- (4- (3-trifluoromethoxybenzyloxycarbonyl) -1-piperazinyl) butyryl group, 4- (4- (3-trifluoromethoxybenzyloxycarbonyl) -1-piperazinyl ) Butyryl group, 5- (4- (3-trifluoromethoxybenzyloxycarbonyl) -1-piperazinyl) pentanoyl group, 3- (4- (4-trifluoromethoxybenzyloxycarbonyl) -1-piperazinyl) butyryl group, 4- (4- (4-t) Trifluoromethoxybenzyloxycarbonyl) -1-piperazinyl) butyryl group, 5- (4- (4-trifluoromethoxybenzyloxycarbonyl) -1-piperazinyl) pentanoyl group, 6- (4- (4-trifluoromethoxybenzyl) group Oxycarbonyl) -1-piperazinyl) hexanoyl group, 4-phenylcarbamoylmethyl-1-piperazinylacetyl group, 3- (4-phenylcarbamoylmethyl-1-piperazinyl) propionyl group, 4- (4-fluorophenylcarbamoylmethyl group) ) -1-Piperazinylacetyl group, 3- (4- (2,3,4,5,6-pentafluorophenylcarbamoylmethyl) -1-piperazinyl) propionyl group, 4- (4-chlorophenylcarbamoylmethyl)- 1-piperazinyl acetyl group, 3 (4- (3,4-Dichlorophenylcarbamoylmethyl) -1-piperazinyl) propionyl group, 4- (4-methylphenylcarbamoylmethyl) -1-piperazinylacetyl group, 3- (4- (2,4-dimethyl) Phenylcarbamoylmethyl) -1-piperazinyl) propionyl group, 4- (4-methoxyphenylcarbamoylmethyl) -1-piperazinylacetyl group, 3- (4- (2,4,6-trimethoxyphenylcarbamoylmethyl)- 1-piperazinyl) propionyl group, 3- (4- (4-trifluoromethylphenylcarbamoylmethyl) -1-piperazinyl) propionyl group, 4- (4-trifluoromethoxyphenylcarbamoylmethyl) -1-piperazinylacetyl group , 3- (4- (4-trifluoromethoxyphenyl) Moylmethyl) -1-piperazinyl) propionyl group, 4-phenylcarbamoyl-1-piperazinylacetyl group, 3- (4-phenylcarbamoyl-1-piperazinyl) propionyl group, 4- (4-fluorophenylcarbamoyl) -1-l Piperazinyl acetyl group




, 3- (4- (2,3,4,5,6-pentafluorophenylcarbamoyl) -1-piperazinyl) propionyl group, 4- (4-chlorophenylcarbamoyl) -1-piperazinylacetyl group, 4- (4- 2,4-Dichlorophenylcarbamoyl) -1-piperazinylacetyl group, 4- (2,6-trichlorophenylcarbamoyl) -1-piperazinylacetyl group, 3- (4- (4-chlorophenylcarbamoyl) -1-) Piperazinyl) propionyl group, 4- (4-methylphenylcarbamoyl) -1-piperazinylacetyl group, 3- (4- (3,4-dimethylphenylcarbamoyl) -1-piperazinyl) propionyl group, 4- (4- (4-methylphenylcarbamoyl) propionyl group Methoxyphenylcarbamoyl) -1-piperazinylacetyl group, 3- [4- (2,4,6-trimethoxyphen) Nilcarbamoyl) -1-piperazinyl] propionyl group, 3- (4- (4-trifluoromethylphenylcarbamoyl) -1-piperazinyl) propionyl group, 4- (3,5-ditrifluoromethoxyphenylcarbamoyl) -1-pipepe Ladinyl acetyl group, 3- (4- (4-trifluoromethoxyphenylcarbamoyl) -1-piperazinyl) propionyl group, 3- (4- (4-fluorophenylcarbamoyl) -1-piperazinyl) propionyl group, 3- (4- (4-fluorophenylcarbamoyl) -1-piperazinyl) propionyl group 4- (4-Methylphenylcarbamoyl) -1-piperazinyl) propionyl group, 3- (4- (4-methoxyphenylcarbamoyl) -1-piperazinyl) propionyl group, 4- (2-benzoxazolyl) -1- Piperazinyl acetyl group, 3- (4- (2-benzoxazolyl) ) -1-Piperazinyl) propionyl group, 4- (4- (2-benzoxazolyl) -1-piperazinyl) butyryl group, 5- (4- (2-benzoxazolyl) -1-piperazinyl) pentanoyl group Piperazinyl C2-6 alkanoyl group such as 6- (4- (2-benzoxazolyl) -1-piperazinyl) hexanoyl group (C1-6 alkanoyl group on piperazine ring, phenyl as a substituent on phenyl ring Having 1 to 5, preferably 1 to 3 groups selected from the group consisting of groups, halogen atoms, halogen-substituted or unsubstituted C1-6 alkyl groups and halogen-substituted or unsubstituted C1-6 alkoxy groups A substituted phenyl C1-6 alkyl group, a halogen atom as a substituent on the phenyl ring, a halogen substituted or unsubstituted C1-6 alkyl group And a phenyl C1-6 alkoxycarbonyl group which may have 1 to 5, preferably 1 to 3 groups selected from the group consisting of halogen-substituted or unsubstituted C1-6 alkoxy groups, and substituents on the phenyl ring As having 1 to 5, preferably 1 to 3 groups selected from the group consisting of halogen atoms, halogen-substituted or unsubstituted C.sub.1-6 alkyl groups and halogen-substituted or unsubstituted C.sub.1-6 alkoxy groups. A group selected from the group consisting of a certain phenylcarbamoyl C1-6 alkyl group, a halogen atom as a substituent, a halogen-substituted or unsubstituted C1-6 alkyl group, and a halogen-substituted or unsubstituted C1-6 alkoxy group on a phenyl ring A phenylcarbamoyl group and a benzoxazolyl group which may have 1 to 5 and preferably 1 to 3 Group selected from the group consisting may have one to three substituents. Can be mentioned.

  Phenylcarbamoyl group (a halogen atom, an amino group which may have a C1-6 alkyl group as a substituent, a carboxyl group, a C1-6 alkoxycarbonyl group, a halogen substituted or unsubstituted C1-6 alkyl group on the phenyl ring) And 1-3 substituted groups selected from the group consisting of halogen-substituted or unsubstituted C1-6 alkoxy groups, piperazinyl groups which may have C1-6 alkyl groups as substituents, and morpholino groups on the piperazine ring, For example, phenylcarbamoyl group, 2-fluorophenylcarbamoyl group, 3-fluorophenylcarbamoyl group, 4-fluorophenylcarbamoyl group, 2-chlorophenylcarbamoyl group, 3-chlorophenylcarbamoyl group, 4-chlorophenyl Carbamoyl group, 2- Mophenylcarbamoyl group, 3-bromophenylcarbamoyl group, 4-bromophenylcarbamoyl group, 2-iodophenylcarbamoyl group, 3-iodophenylcarbamoyl group, 4-iodophenylcarbamoyl group, 2,3-difluorophenylcarbamoyl group, 3 , 4-Difluorophenylcarbamoyl group, 3,5-difluorophenylcarbamoyl group, 2,4-difluorophenylcarbamoyl group, 2,6-difluorophenylcarbamoyl group, 2,3-dichlorophenylcarbamoyl group, 3,4-dichlorophenylcarbamoyl group 3,5-dichlorophenylcarbamoyl group, 2,4-dichlorophenylcarbamoyl group, 2,6-dichlorophenylcarbamoyl group, 3,4,5-trifluorophenylcarbamoyl group, 2,3-di Fluorophenylcarbamoyl group, 3,4,5-trichlorophenylcarbamoyl group, 2,4,6-trifluorophenylcarbamoyl group, 2,4,6-trichlorophenylcarbamoyl group, 2-methylphenylcarbamoyl group, 3-methyl Phenylcarbamoyl group, 4-methylphenylcarbamoyl group, 2-methyl-3-chlorophenylcarbamoyl group, 3-methyl-4-chlorophenylcarbamoyl group, 2-chloro-4-methylphenylcarbamoyl group, 2-methyl-3-fluorophenyl Carbamoyl group, 2-trifluoromethylphenylcarbamoyl group, 3-trifluoromethylphenylcarbamoyl group, 4-trifluoromethylphenylcarbamoyl group, N-methyl-N-phenylcarbamoyl group, N- (2-fluorophenyl)- N-methylcarbamoyl group, N- (3-fluorophenyl) -N-methylcarbamoyl group, N- (4-fluorophenyl) -N-methylcarbamoyl group, N- (2-chlorophenyl) -N-methylcarbamoyl group, N- (3-chlorophenyl) -N-methylcarbamoyl group, N- (4-chlorophenyl) -N-methylcarbamoyl group, N- (4-bromophenyl) -N-methylcarbamoyl group, N- (2-iodophenyl) ) -N-methylcarbamoyl group, N- (3-iodophenyl) -N-methylcarbamoyl group, N- (4-iodophenyl) -N-methylcarbamoyl group, N- (2,3-difluorophenyl) -N -Methylcarbamoyl group, N- (3,4-difluorophenyl) -N-methylcarbamoyl group, N- (3,5-difluorophenyl) Group), N- (2,4-difluorophenyl) -N-methylcarbamoyl group, N- (2,6-difluorophenyl) -N-methylcarbamoyl group, N- (2,3-difluorocarbyl) group, Dichlorophenyl) -N-methylcarbamoyl group, N- (3,4-dichlorophenyl) -N-methylcarbamoyl group, N- (3,5-dichlorophenyl) -N-methylcarbamoyl group, N- (2,4-dichlorophenyl) group -N-methylcarbamoyl group, N- (2,6-dichlorophenyl) -N-methylcarbamoyl group, N- (3,4,5-trifluorophenyl) -N-methylcarbamoyl group, N- (3,4,6 5-trichlorophenyl) -N-methylcarbamoyl group, N- (2,4,6-trifluorophenyl) -N-methylcarbamoyl group, N- 2,4,6-trichlorophenyl) -N-methylcarbamoyl group, N- (2-methylphenyl) -N-methylcarbamoyl group, N- (3-methylphenyl) -N-methylcarbamoyl group, N- (4) -Methylphenyl) -N-methylcarbamoyl group, N- (2-methyl-3-chlorophenyl) -n-methylcarbamoyl group, N- (3-methyl-4-chlorophenyl) -N-methylcarbamoyl group, N- ( 2-chloro-4-methylphenyl) -N-methylcarbamoyl group, N- (2-methyl-3-fluorophenyl) -N-methylcarbamoyl group, N- (2-trifluoromethylphenyl) -N-methylcarbamoyl Group, N- (4-trifluoromethylphenyl) -N-methylcarbamoyl group, N-benzyl-N-phenylcarbamoyl group, N- Benzyl-N- (2-fluorophenyl) carbamoyl group, N-benzyl-N- (3-fluorophenyl) carbamoyl group, N-benzyl-N- (4-fluorophenyl) carbamoyl group, N-benzyl-N- ( 2-chlorophenyl) carbamoyl group, N-benzyl-N- (3-chlorophenyl) carbamoyl group, N-benzyl-N- (4-chlorophenyl) carbamoyl group, N-benzyl-N- (2-bromophenyl) carbamoyl group, N-benzyl-N- (3-bromophenyl) carbamoyl group, N-benzyl-N- (4-bromophenyl) carbamoyl group, N-benzyl-N- (2-iodophenyl) carbamoyl group, N-benzyl-N -(3-iodophenyl) carbamoyl group, N-benzyl-N- (4-iodophenyl) carbamoyl group Group, N-benzyl-N- (2,3-difluorophenyl) carbamoyl group, N-benzyl-N- (3,4-difluorophenyl) carbamoyl group, N-benzyl-N- (3,5-difluorophenyl) ) Carbamoyl group, N-benzyl-N- (2,4-difluorophenyl) carbamoyl group, N-benzyl-N- (2,6-difluorophenyl) carbamoyl group, N-benzyl-N- (2,3-dichlorophenyl) ) Carbamoyl group, N-benzyl-N- (3,4-dichlorophenyl) carbamoyl group, N-benzyl-N- (3,5-dichlorophenyl) carbamoyl group, N-benzyl-N- (2,4-dichlorophenyl) carbamoyl group Group, N-benzyl-N- (2,6-dichlorophenyl) carbamoyl group, N-benzyl-N- (3,4,6 -Trifluorophenyl) carbamoyl group, N-benzyl-N- (3,4,5-trichlorophenyl) carbamoyl group, N-benzyl-N- (2,3-difluorophenyl) carbamoyl group, N-benzyl-N- (2,4,6-trichlorophenyl) carbamoyl group, N-benzyl-N- (2-methylphenyl) carbamoyl group, N-benzyl-N- (3-methylphenyl) carbamoyl group, N-benzyl-N- ( 4-Methylphenyl) carbamoyl group, N-benzyl-N- (2-methyl-3-chlorophenyl) carbamoyl group, N-benzyl-N- (3-methyl-4-chlorophenyl) carbamoyl group, N-benzyl-N- (2-chloro-4-methylphenyl) carbamoyl group, N-benzyl-N- (2-methyl-3-fluorophenyl) Carbamoyl group, N-benzyl-N- (2-trifluoromethylphenyl) carbamoyl group, N-benzyl-N- (3-trifluoromethylphenyl) carbamoyl group, N-benzyl-N- (4-trifluoromethylphenyl) ) Carbamoyl group, 2-pentafluoroethylphenylcarbamoyl group, 3-pentafluoroethylphenylcarbamoyl group, 4-pentafluoroethylphenylcarbamoyl group, 2-isopropylphenylcarbamoyl group, 3-isopropylphenylcarbamoyl group, 4-isopropylphenylcarbamoyl group Group, 2-tert-butylphenylcarbamoyl group, 3-tert-butylphenylcarbamoyl group, 4-tert-butylphenylcarbamoyl group, 2-sec-butylphenylcarbamoyl group, 3-s c-Butylphenylcarbamoyl group, 4-sec-butylphenylcarbamoyl group, 2-n-heptafluoropropylphenylcarbamoyl group, 3-n-heptafluoropropylphenylcarbamoyl group, 4-n-heptafluoropropylphenylcarbamoyl group, 4 -Pentylphenylcarbamoyl group, 4-hexylphenylcarbamoyl group, 2-methoxyphenylcarbamoyl group, 3-methoxyphenylcarbamoyl group, 4-methoxyphenylcarbamoyl group, 2-methoxy-3-chlorophenylcarbamoyl group, 2-fluoro-3- Methoxyphenylcarbamoyl group, 2-fluoro-4-methoxyphenylcarbamoyl group, 2,6-dimethoxyphenylcarbamoyl group, 2,3,4-trifluorophenylcarbamoyl group, 3,4,5 -Trifluorophenylcarbamoyl group, 2-trifluoromethoxyphenylcarbamoyl group, 3-trifluoromethoxyphenylcarbamoyl group, 4-trifluoromethoxyphenylcarbamoyl group, 2-pentafluoroethoxyphenylcarbamoyl group, 3-pentafluoroethoxyphenylcarbamoyl group Group, 4-pentafluoroethoxyphenylcarbamoyl group, 2-isopropoxyphenylcarbamoyl group, 3-isopropoxyphenylcarbamoyl group, 4-isopropoxyphenylcarbamoyl group, 2-tert-butoxyphenylcarbamoyl group, 3-tert-butoxyphenyl group Carbamoyl group, 4-tert-butoxyphenylcarbamoyl group, 2-sec-butoxyphenylcarbamoyl group, 3-sec-butoxyphenyne Carbamoyl group, 4-sec-butoxyphenylcarbamoyl group, 2-n-heptafluoropropoxyphenylcarbamoyl group, 3-n-heptafluoropropoxyphenylcarbamoyl group, 4-n-heptafluoropropoxyphenylcarbamoyl group, 4-pentyloxyphenyl Carbamoyl group, 4-hexyloxyphenylcarbamoyl group, 2-dimethylaminophenylcarbamoyl group, 2-aminophenylcarbamoyl group, 2,4-diaminophenylcarbamoyl group, 2,4,6-triaminophenylcarbamoyl group, 3-dimethyl Aminophenylcarbamoyl group, 4-methylaminophenylcarbamoyl group, 2-carboxylphenylcarbamoyl group, 3-carboxylphenylcarbamoyl group, 4-carboxylphenyl group Moyl group, 2,3-dicarboxylphenylcarbamoyl group, 2,4,6-tricarboxylphenylcarbamoyl group, 2-methoxycarbonylphenylcarbamoyl group, 3-methoxycarbonylphenylcarbamoyl group, 4-methoxycarbonylphenylcarbamoyl group, 2 -Ethoxycarbonylphenylcarbamoyl group, 3-ethoxycarbonylphenylcarbamoyl group, 4-ethoxycarbonylphenylcarbamoyl group, 2-propoxycarbonylphenylcarbamoyl group, 3-propoxycarbonylphenylcarbamoyl group, 4-propoxycarbonylphenylcarbamoyl group, 2- (2-) 1-piperazinyl) phenylcarbamoyl group, 2- (2,4-dimethyl-1-piperazinyl) phenylcarbamoyl group, 2- (2,3,4-trime Tyl-1-piperazinyl) phenylcarbamoyl group, 2- (4-methyl-1-piperazinyl) phenylcarbamoyl group, 3- (4-methyl-1-piperazinyl) phenylcarbamoyl group, 4- (4-methyl-1-piperazinyl) group ) Phenylcarbamoyl groups such as phenylcarbamoyl group, 2-morpholinophenylcarbamoyl group, 3-morpholinophenylcarbamoyl group, 4-morpholinophenylcarbamoyl group (a halogen atom on a phenyl ring, and a C1-6 alkyl group as a substituent) Substituents on an amino group, carboxyl group, C1-6 alkoxycarbonyl group, halogen substituted or unsubstituted C1-6 alkyl group, halogen substituted or unsubstituted C1-6 alkoxy group, piperazine ring which may have 2 to 2 C1-6 alkyl group as 1 to 3 One to three groups selected from the group consisting of piperazinyl and morpholino which may be substituted may be substituted, and another C1 to C6 alkyl group or a phenyl C1 to C6 alkyl group is substituted to the amino group portion May be mentioned).

  Phenyl C1-6 alkyl carbamoyl group (wherein at least one group selected from the group consisting of a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group on the phenyl ring is As optionally substituted), for example, benzylcarbamoyl group, 1-phenylethylcarbamoyl group, 2-phenylethylcarbamoyl group, 3-phenylpropylcarbamoyl group, 4-phenylbutylcarbamoyl group, 5-phenylpentylcarbamoyl group, 6-phenylhexylcarbamoyl group, 2-methyl-3-phenylpropylcarbamoyl group, 1,1-dimethyl-2-phenylethylcarbamoyl group, 2-methylbenzylcarbamoyl group, 3-methylbenzylcarbamoyl group, 4-methylbenzylcarbamoyl group Group, 2,4-dimethylbenzylcarbamoyl group, 2,4,6-trimethylbenzylcarbamoyl group, 4-trifluoromethyl-3-methoxybenzylcarbamoyl group, 2-ethylbenzylcarbamoyl group, 3-ethylbenzylcarbamoyl group, 4 4-ethylbenzylcarbamoyl group, 2-isopropylbenzylcarbamoyl group, 3-isopropylbenzylcarbamoyl group, 4-isopropylbenzylcarbamoyl group, 2,4-dimethoxybenzylcarbamoyl group, 2,4,6-trimethoxybenzylcarbamoyl group, 4- Trifluoromethoxy-3-methylbenzylcarbamoyl group, 4-methoxybenzylcarbamoyl group, 2-ethoxybenzylcarbamoyl group, 3-ethoxybenzylcarbamoyl group, 4-ethoxybenzylcarbamoyl group 2-isopropoxybenzylcarbamoyl group, 3-isopropoxybenzylcarbamoyl group, 4-isopropoxybenzylcarbamoyl group, 4-trifluoromethylbenzylcarbamoyl group, 4-pentafluoroethylbenzylcarbamoyl group, 4-n-heptafluoropropylbenzyl Phenyl C1-6 alkylcarbamoyl groups such as carbamoyl group, 4-trifluoromethoxybenzylcarbamoyl group, 4-pentafluoroethoxybenzylcarbamoyl group, 4-n-heptafluoropropoxybenzyl carbamoyl group (on the phenyl ring, halogen substituted or substituted; And the group selected from the group consisting of an unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted with 1 to 3 groups.

  Piperazinyl carbonyl group (C.sub.1-6 alkoxycarbonyl group, phenyl C.sub.1-6 alkoxycarbonyl group on the piperazine ring [in the phenyl ring, at least one halogen-substituted or unsubstituted C.sub.1-6 alkyl group is substituted. And phenyl C1-6 alkyl group [wherein at least one halogen-substituted or unsubstituted C1-6 alkyl group may be substituted on the phenyl ring] As at least one type of the substituent, for example, 1-piperazinylcarbonyl group, 2-piperazinylcarbonyl group, 3-piperazinylcarbonyl group, 4-piperazinylcarbonyl group, 4- tert-Butoxycarbonyl-1-piperazinylcarbonyl group, 4- (4-methylbenzyloxycarbonyl) -1-pipe Dinylcarbonyl group, 4- (2,4-dimethylbenzyloxycarbonyl) -1-piperazinylcarbonyl group, 4- (2,4,6-trimethylbenzyloxycarbonyl) -1-piperazinylcarbonyl group, 4 -(4-Trifluoromethylbenzyloxycarbonyl) -1-piperazinylcarbonyl group, 4- (4-methylbenzyl) -1-piperazinylcarbonyl group, 4- (3,4-dimethylbenzyl) -1- Piperazinyl carbonyl group, 4- (3,4,5-trimethylbenzyl) -1-piperazinyl carbonyl group, 4- (4-trifluoromethylbenzyl) -1-piperazinyl carbonyl group, 4-methoxycarbonyl group -3-benzyl-1-piperazinylcarbonyl group, 4-benzyloxycarbonyl-3,5-dimethoxycarbonyl-1 Piperazinyl carbonyl group such as piperazinyl carbonyl group (C1-6 alkoxycarbonyl group on piperazine ring, halogen substituted or unsubstituted C1 to C3 alkyl group on phenyl ring) A group selected from the group consisting of a phenyl C1-6 alkoxycarbonyl group and a phenyl C1-6 alkyl group which may have 1 to 3 halogen-substituted or unsubstituted C1-6 alkyl groups on the phenyl ring is 1 to 3 ) May be mentioned.

  In the present specification, each group represented by (a) to (y) is specifically as follows.

  As a halogen atom, a fluorine atom, a chlorine atom, a bromine atom and an iodine atom are shown.

  The C1-6 alkyl group is a linear or branched alkyl group having 1 to 6 carbon atoms, and examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group and an n- group. A butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, an n-pentyl group, a neopentyl group, an n-hexyl group, an isohexyl group, a 3-methylpentyl group and the like can be mentioned.

  The C1-6 alkoxy group is a group composed of a C1-6 alkyl group as defined above and an oxygen atom, and for example, a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group And isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, n-hexyloxy, isohexyloxy, 3-methylpentoxy and the like.

  The halogen-substituted or unsubstituted C1-6 alkyl group is a linear or branched alkyl group having 1 to 6 carbon atoms as defined above, and the above-mentioned alkyl in which 1 to 7 halogen atoms are substituted. Group, for example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, n-pentyl group, neopentyl group, n-hexyl group Group, isohexyl group, 3-methylpentyl group, fluoromethyl group, difluoromethyl group, trifluoromethyl group, chloromethyl group, dichloromethyl group, trichloromethyl group, bromomethyl group, dibromomethyl group, dichlorofluoromethyl group, 2,2-trifluoroethyl group, pentafluoroethyl group, 2-chloroethyl group, 3,3,3-t Fluoropropyl group, heptafluoropropyl group, heptafluoroisopropyl group, 3-chloropropyl group, 2-chloropropyl group, 3-bromopropyl group, 4,4,4-trifluorobutyl group, 4,4,4,3 trifluorobutyl group , 3-pentafluorobutyl group, 4-chlorobutyl group, 4-bromobutyl group, 2-chlorobutyl group, 5,5,5-trifluoropentyl group, 5-chloropentyl group, 6,6,6-trifluorohexyl group Group, 6-chlorohexyl group etc. can be mentioned.

  The halogen-substituted or unsubstituted C1-6 alkoxy group is a C1-6 alkoxy group as defined above and the above alkoxy group substituted by 1 to 7 halogen atoms, and examples thereof include a methoxy group, an ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, tert-butoxy group, sec-butoxy group, n-pentoxy group, neopentoxy group, n-hexyloxy group, isohexyloxy group, 3-methyl pen Toxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chloromethoxy, dichloromethoxy, trichloromethoxy, bromomethoxy, dibromomethoxy, dichlorofluoromethoxy, 2,2,2-trifluoroethoxy Group, pentafluoroethoxy group, 2-chloroet Group, 3,3,3-trifluoropropoxy group, heptafluoropropoxy group, heptafluoroisopropoxy group, 3-chloropropoxy group, 2-chloropropoxy group, 3-bromopropoxy group, 4,4,4-trithio Fluorobutoxy group, 4,4,4,3,3-pentafluorobutoxy group, 4-chlorobutoxy group, 4-bromobutoxy group, 2-chlorobutoxy group, 5,5,5-trifluoropentoxy group, 5 -Chloropentoxy group, 6,6, 6- trifluorohexyloxy group, 6-chlorohexyloxy group etc. can be mentioned.

  A phenoxy group (in which at least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group is substituted on a phenyl ring; As phenoxy group, 2-fluorophenoxy group, 3-fluorophenoxy group, 4-fluorophenoxy group, 2-chlorophenoxy group, 3-chlorophenoxy group, 4-chlorophenoxy group, and the like. -Bromophenoxy group, 3-bromophenoxy group, 4-bromophenoxy group, 2,3-dichlorophenoxy group, 3,4-dichlorophenoxy group, 2,4-dichlorophenoxy group, 3,4,5-trichlorophenoxy group 2,4,6-trichlorophenoxy group 2,3,4,5,6-pentafluorophenoxy , 2-methylphenoxy group, 3-methylphenoxy group, 4-methylphenoxy group, 2-ethylphenoxy group, 3-ethylsiphenoxy group, 4-ethylphenoxy group, 4-n-propylphenoxy group, 4-tert- Butylphenoxy, 4-n-butylphenoxy, 2-trifluoromethylphenoxy, 3-trifluoromethylphenoxy, 4-trifluoromethylphenoxy, 2-pentafluoroethylphenoxy, 3-pentafluoroethylphenoxy Group, 2,3-dimethylphenoxy group, 3,4,5-trimethylphenoxy group, 4-n-pentylphenoxy group, 4-n-hexylphenoxy group, 2-methoxyphenoxy group, 3-methoxyphenoxy group, 4- Methoxyphenoxy group, 2-ethoxyphenoxy group, 3-etokiki Phenoxy group, 4-ethoxyphenoxy group, 4-n-propoxyphenoxy group, 4-tert-butoxyphenoxy group, 4-n-butoxyphenoxy group, 2-trifluoromethoxyphenoxy group, 3-trifluoromethoxyphenoxy group, 4 -Trifluoromethoxyphenoxy group, 2-pentafluoroethoxyphenoxy group, 3-pentafluoroethoxyphenoxy group, 2,3-dimethoxyphenoxy group, 3,4,5-trimethoxyphenoxy group, 4-n-pentyloxyphenoxy group Or a phenoxy group such as 4-n-hexyloxyphenoxy group (from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group on the phenyl ring 1 to 5 selected groups, preferably 1 to 3 may be substituted).

  Piperidyl group [in which at least one phenoxy group (on the phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group are formed on the phenyl ring At least one group selected from the group may be substituted), for example, 1-piperidyl group, 4-piperidyl group, 2-piperidyl group, 3-piperidyl group 4-phenoxy-1-piperidyl group, 2,4-diphenoxy-1-piperidyl group, 2,4,6-triphenoxy-1-piperidyl group, 2- (2-fluorophenoxy) -1-piperidyl group, 3 -(3-fluorophenoxy) -2-piperidyl group, 4- (4-fluorophenoxy) -3-piperidyl group, 2- (2-chlorophenoxy) -4-pi Lysyl group, 3- (3-chlorophenoxy) -5-piperidyl group, 4- (4-chlorophenoxy) -2-piperidyl group, 5- (2-bromophenoxy) -2-piperidyl group, 6- (3- (3-bromophenoxy) -2-piperidyl group Bromophenoxy) -3-piperidyl group, 4- (4-bromophenoxy) -1-piperidyl group, 3- (2,3-dichlorophenoxy) -2-piperidyl group, 4- (3,4-dichlorophenoxy)- 3-piperidyl group, 3- (2,4-dichlorophenoxy) -4-piperidyl group, 2- (3,4,5-trichlorophenoxy) -3-piperidyl group, 6- (2,4,6-trichlorophenoxy group) ) -2-Piperidyl group, 3- (2,3,4,5,6-pentafluorophenoxy) -1-piperidyl group, 4- (2-methylphenoxy) -1-piperidyl group, 5- (3-methyl-3-vinyl) Phenoxy) -2-piperidyl group, 6- (4-methyl phenoxy) -3-piperidyl group, 1- (2-ethyl phenoxy) -4-piperidyl group, 2- (3-ethyl cyphenoxy) -1-piperidyl Group, 3- (4-ethylphenoxy) -2-piperidyl group, 4- (4-n-propylphenoxy) -3-piperidyl group, 3- (4-tert-butylphenoxy) -4-piperidyl group, 2- (4-n-butylphenoxy) -3-piperidyl group, 1- (2-trifluoromethylphenoxy) -2-piperidyl group, 2- (3-trifluoromethylphenoxy) -1-piperidyl group, 3- (4 -Trifluoromethylphenoxy) -1-piperidyl group, 1- (2-pentafluoroethyl phenoxy) -4-piperidyl group, 1- (3-pentafluoroethyl phenyl) Phenoxy) 4-piperidyl group, 4- (2,3-dimethylphenoxy) -1-piperidyl group, 1- (3,4,5-trimethylphenoxy) -4-piperidyl group, 1- (4-n-pentyl) group Phenoxy) -4-piperidyl group, 4- (4-n-hexylphenoxy) -1-piperidyl group, 4- (2-methoxyphenoxy) -1-piperidyl group, 1- (3-methoxyphenoxy) -4-piperidyl Group, 1- (4-methoxyphenoxy) -4-piperidyl group, 2- (2-ethoxyphenoxy) -3-piperidyl group, 3- (3-ethoxyphenoxy) -4-piperidyl group, 4- (4-ethoxy) group Phenoxy) -3-piperidyl group, 3- (4-n-propoxyphenoxy) -2-piperidyl group, 2- (4-tert-butoxyphenoxy) -1-piperidyl group 1- (4-n-butoxyphenoxy) -2-piperidyl group, 2- (2-trifluoromethoxyphenoxy) -3-piperidyl group, 3- (3-trifluoromethoxyphenoxy) -4-piperidyl group, 4- (4-Trifluoromethoxyphenoxy) -3-piperidyl group, 3- (2-pentafluoroethoxyphenoxy) -2-piperidyl group, 2- (4-pentafluoroethoxyphenoxy) -1-piperidyl group, 1- (2 4, 3-Dimethoxyphenoxy) -4-piperidyl group, 4- (3,4,5-trimethoxyphenoxy) -1-piperidyl group, 4- (4-n-pentyloxyphenoxy) -1-piperidyl group, 4- Piperidyl groups such as (4-n-hexyloxyphenoxy) -1-piperidyl group [1 to 3 phenoxy groups on the piperidine ring On the phenyl ring, 1 to 5 groups, preferably 1 to 6 groups selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group are preferable. And the like) may be substituted.

  A phenyl group (on the phenyl ring, at least one piperidyl group [on the piperidine ring, at least one phenoxy group (on the phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group, At least one of a group selected from the group consisting of a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted) may be substituted), For example, phenyl group, 4- (1-piperidyl) phenyl group, 2,4-di (1-piperidyl) phenyl group, 2,4,6-tri (1-piperidyl) phenyl group, 3- (4-piperidyl) Phenyl group, 2- (2-piperidyl) phenyl group, 4- (3-piperidyl) phenyl group, 3- (4-phenoxy-1-piperidyl) phenyl group, 2- (2,4-diphenoxy-1) Piperidyl) phenyl, 4- (2,4,6-triphenoxy-1-piperidyl) phenyl, 3- [2- (2-fluorophenoxy) -1-piperidyl] phenyl, 2- [3- (3) -Fluorophenoxy) -2-piperidyl] phenyl group, 4- [4- (4-fluorophenoxy) -3-piperidyl] phenyl group, 3- [2- (2-chlorophenoxy) -4-piperidyl] phenyl group, 2- [3- (3-chlorophenoxy) -5-piperidyl] phenyl group, 4- [4- (4-chlorophenoxy) -2-piperidyl] phenyl group, 3- [5- (2-bromophenoxy)- 2-piperidyl] phenyl group, 2- [6- (3-bromophenoxy) -3-piperidyl] phenyl group, 4- [4- (4-bromophenoxy) -1-piperidyl] phenyl , 3- [3- (2,3-dichlorophenoxy) -2-piperidyl] phenyl group, 2- [4- (3,4-dichlorophenoxy) -3-piperidyl] phenyl group, 4- [3- (2) , 4-Dichlorophenoxy) -4-piperidyl] phenyl group, 3- [2- (3,4,5-trichlorophenoxy) -3-piperidyl] phenyl group, 2- [6- (2,4,6-trichloro) Phenoxy) -2-piperidyl] phenyl group, 4- [3- (2,3,4,5,6-pentafluorophenoxy) -1-piperidyl] phenyl group, 3- [4- (2-methylphenoxy)- 1-piperidyl! Phenyl group, 2- [5- (3-methylphenoxy) -2-piperidyl] phenyl group, 4- [6- (4-methylphenoxy) -3-piperidyl] phenyl group, 3- [1-] (2-ethyl Phenoxy) -4-piperidyl] phenyl group, 2- [2- (3-ethyl phenoxy) -1-piperidyl] phenyl group, 4- [3- (4-ethyl phenoxy) -2-piperidyl] phenyl group, 3- [4- (4-n-propylphenoxy) -3-piperidyl] phenyl group, 2- [3- (4-tert-butylphenoxy) -4-piperidyl] phenyl group, 4- [2- (4-n-) Butylphenoxy) -3-piperidyl] phenyl group, 3- [1- (2-trifluoromethylphenoxy) -2-piperidyl] phenyl group, 2- [2- (3-trifluoromethylphenoxy) -1-piperidyl] Phenyl group, 4- [3- (4-trifluoromethylphenoxy) -1-piperidyl] phenyl group, 3- [1- (2-pentafluoroethyl phenoxy) -4-pi] Lysyl] phenyl group, 2- [1- (3-pentafluoroethyl phenoxy) -4-piperidyl] phenyl group, 4- [4- (2,3-dimethylphenoxy) -1-piperidyl] phenyl group, 3- [4 1- (3,4,5-trimethylphenoxy) -4-piperidyl] phenyl group, 2- [1- (4-n-pentylphenoxy) -4-piperidyl] phenyl group, 4- [4- (4-n) -Hexylphenoxy) -1-piperidyl] phenyl group, 3- [4- (2-methoxyphenoxy) -1-piperidyl] phenyl group, 2- [1- (3-methoxyphenoxy) -4-piperidyl] phenyl group, 4- [1- (4-methoxyphenoxy) -4-piperidyl] phenyl group, 3- [2- (2-ethoxyphenoxy) -3-piperidyl] phenyl group, 2- [3- (3- (3-) Toxiphenoxy) -4-piperidyl] phenyl group, 4- [4- (4-ethoxyphenoxy) -3-piperidyl] phenyl group, 3- [3- (4-n-propoxyphenoxy) -2-piperidyl] phenyl group , 2- [2- (4-tert-butoxyphenoxy) -1-piperidyl] phenyl group, 4- [1- (4-n-butoxyphenoxy) -2-piperidyl] phenyl group, 3- [2- (2 (2-) -Trifluoromethoxyphenoxy) -3-piperidyl] phenyl group, 2- [3- (3-trifluoromethoxyphenoxy) -4-piperidyl] phenyl group, 4- [4- (4-trifluoromethoxyphenoxy) -1 -Piperidyl] phenyl group, 3- [3- (2-pentafluoroethoxyphenoxy) -2-piperidyl] phenyl group, 2- [2- (4-pen] Tafluoroethoxyphenoxy) -1-piperidyl] phenyl group, 4- [1- (2,3-dimethoxyphenoxy) -4-piperidyl] phenyl group, 3- [4- (3,4,5-trimethoxyphenoxy) phenyl group -1-piperidyl! Phenyl group, 2- [4- (4-n-pentyloxyphenoxy) -1-piperidyl] phenyl group, 4- [4- (4-n-hexyloxyphenoxy) -1-piperidyl] phenyl A phenyl group such as a group (one to three piperidyl groups on the phenyl ring [one to three phenoxy groups on the piperidine ring (a halogen atom on the phenyl ring, halogen substituted or unsubstituted C1 1 to 5, preferably 1 to 3 groups selected from the group consisting of a -6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted There may be] it can be mentioned may) be substituted.

  Phenyl group [in which at least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group is substituted on a phenyl ring And the like] is selected from the group consisting of unsubstituted phenyl group and the halogen atom as defined above, halogen substituted or unsubstituted C1-6 alkyl group and halogen substituted or unsubstituted C1-6 alkoxy group A phenyl group having 1 to 5, preferably 1 to 3 substituents, such as phenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 2-bromophenyl group, 3-bromophenyl group, 4-bromophenyl group, 2- Dophenyl group, 3-iodophenyl group, 4-iodophenyl group, 2,3-difluorophenyl group, 3,4-difluorophenyl group, 3,5-difluorophenyl group, 2,4-difluorophenyl group, 2, 6 -Difluorophenyl group, 2,3-dichlorophenyl group, 3,4-dichlorophenyl group, 3,5-dichlorophenyl group, 2,4-dichlorophenyl group, 2,6-dichlorophenyl group, 3,4,5-trifluorophenyl group 3,4,5-trichlorophenyl group, 2,4,6-trifluorophenyl group, 2,4,6-trichlorophenyl group, 2-fluoro-4-bromophenyl group, 4-chloro-3-fluorophenyl group Group, 2,3,4-trichlorophenyl group, 2,3,4,5,6-pentafluorophenyl group, 2,4,6-trimethyl group , 4-n-butylphenyl, 2,4-dimethylphenyl, 2,3-dimethylphenyl, 2,6-dimethylphenyl, 3,5-dimethylphenyl, 2,5-dimethylphenyl 3,5-Ditrifluoromethylphenyl group, 4-n-butoxyphenyl group, 2,4-dimethoxyphenyl group, 2,3-dimethoxyphenyl group, 2,6-dimethoxyphenyl group, 3,5-dimethoxyphenyl group , 2,5-Dimethoxyphenyl group, 2,4,6-trimethoxyphenyl group, 3,5-ditrifluoromethoxyphenyl group, 3-chloro-4-methoxyphenyl group, 2-chloro-4-trifluoromethoxyphenyl group Group, 3-methyl-4-fluorophenyl group, 4-bromo-3-trifluoromethylphenyl group, 2-methylphenyl group, 3- Tylphenyl group, 4-methylphenyl group, 2-methyl-3-chlorophenyl group, 3-methyl-4-chlorophenyl group, 2-chloro-4-methylphenyl group, 2-methyl-3-fluorophenyl group, 2-trile Fluoromethylphenyl group, 3-trifluoromethylphenyl group, 4-trifluoromethylphenyl group, 2-pentafluoroethylphenyl group, 3-pentafluoroethylphenyl group, 4-pentafluoroethylphenyl group, 2-isopropylphenyl group , 3-isopropylphenyl group, 4-isopropylphenyl group, 2-tert-butylphenyl group, 3-tert-butylphenyl group, 4-tert-butylphenyl group, 2-sec-butylphenyl group, 3-sec-butyl Phenyl group, 4-sec-butylphenyl group, 2-n-ha Tafluoropropylphenyl group, 3-n-heptafluoropropylphenyl group, 4-n-heptafluoropropylphenyl group, 4-pentylphenyl group, 4-hexylphenyl group, 2-methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 3-chloro-2-methoxyphenyl group, 2-fluoro-3-methoxyphenyl group, 2-fluoro-4-methoxyphenyl group, 2,3,4-trifluorophenyl group, 2-trile Fluoromethoxyphenyl group, 3-trifluoromethoxyphenyl group, 4-trifluoromethoxyphenyl group, 3-fluoro-2-trifluoromethoxyphenyl group, 2-fluoro-3-trifluoromethoxyphenyl group, 3-fluoro-4 -Trifluoromethoxyphenyl group, 3-chloro-2-triflule Lomethoxyphenyl group, 2-chloro-3-trifluoromethoxyphenyl group, 3-chloro-4-trifluoromethoxyphenyl group, 2-pentafluoroethoxyphenyl group, 3-pentafluoroethoxyphenyl group, 4-pentafluoroethoxy Phenyl group, 3-chloro-2-pentafluoroethoxyphenyl group, 2-chloro-3-pentafluoroethoxyphenyl group, 3-chloro-4-pentafluoroethoxyphenyl group, 2-isopropoxyphenyl group, 3-isopropoxy Phenyl group, 4-isopropoxyphenyl group, 2-tert-butoxyphenyl group, 3-tert-butoxyphenyl group, 4-tert-butoxyphenyl group, 2-sec-butoxyphenyl group, 3-sec-butoxyphenyl group, 4-sec-butoxyphenyl Group, 2-n-heptafluoropropoxyphenyl group, 3-n-heptafluoropropoxyphenyl group, 4-n-heptafluoropropoxyphenyl group, 4-n-pentoxyphenyl group, 4-n-hexyloxyphenyl group etc. Can be mentioned.

  Examples of the phenyl C1-6 alkyl group include benzyl group, 1-phenethyl group, 2-phenethyl group, 3-phenylpropyl group, 2-phenylpropyl group, 4-phenylbutyl group, 5-phenylpentyl group, 4- Examples include phenylpentyl group, 6-phenylhexyl group, 2-methyl-3-phenylpropyl group, 1,1-dimethyl-2-phenylethyl group and the like.

  Phenyl C1-6 alkyl group (wherein at least one of the groups selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group on the phenyl ring The term “optionally substituted” means an unsubstituted phenyl C1-6 alkyl group, and a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted group on the phenyl ring constituting those groups. A group selected from the group consisting of unsubstituted C1-6 alkoxy groups substituted with 1 to 5, preferably 1 to 3 groups, and examples thereof include benzyl group, 1-phenethyl group and 2-phenethyl group Group, 3-phenylpropyl group, 2-phenylpropyl group, 4-phenylbutyl group, 5-phenylpentyl group, 4-phenylpentyl group, -Phenylhexyl group, 2-fluorobenzyl group, 3-fluorobenzyl group, 4-fluorobenzyl group, 2-chlorobenzyl group, 3-chlorobenzyl group, 4-chlorobenzyl group, 2-bromobenzyl group, 3-bromo Benzyl, 4-bromobenzyl, 2-iodobenzyl, 3-iodobenzyl, 4-iodobenzyl, 2,3-difluorobenzyl, 3,4-difluorobenzyl, 3,5-difluorobenzyl 2,4-difluorobenzyl group, 2,6-difluorobenzyl group, 2,3-dichlorobenzyl group, 3,4-dichlorobenzyl group, 3,5-dichlorobenzyl group, 2,4-dichlorobenzyl group, 2 , 6-dichlorobenzyl group, 2-fluoro-4-bromobenzyl group, 4-chloro-3-fluorobenzyl group, 2, 3, 4 Trichlorobenzyl group, 3,4,5-trifluorobenzyl group, 2,4,6-trichlorobenzyl group, 4-isopropylbenzyl group, 4-n-butylbenzyl group, 4-methylbenzyl group, 2-methylbenzyl group , 3-methylbenzyl group, 2,4-dimethylbenzyl group, 2,3-dimethylbenzyl group, 2,6-dimethylbenzyl group, 3,5-dimethylbenzyl group, 2,5-dimethylbenzyl group, 2,4 , 6-trimethylbenzyl, 3,5-ditrifluoromethylbenzyl, 2,3,4,5,6-pentafluorobenzyl, 4-isopropoxybenzyl, 4-n-butoxybenzyl, 4-methoxy Benzyl group, 2-methoxybenzyl group, 3-methoxybenzyl group, 2,4-dimethoxybenzyl group, 2,3-dimethoxybenzyl group, 2, 6-dimethoxybenzyl group, 3,5-dimethoxybenzyl group, 2,5-dimethoxybenzyl group, 2,4,6-trimethoxybenzyl group, 3,5-ditrifluoromethoxybenzyl group, 2-isopropoxybenzyl group, 3-chloro-4-methoxybenzyl group, 2-chloro-4-trifluoromethoxybenzyl group, 3-methyl-4-fluorobenzyl group, 4-bromo-3-trifluoromethylbenzyl group, 2-trifluoromethylbenzyl group Group, 3-trifluoromethylbenzyl group, 4-trifluoromethylbenzyl group, 2-pentafluoroethyl benzyl group, 3-pentafluoroethyl benzyl group, 4-pentafluoroethyl benzyl group, 2-trifluoromethoxybenzyl group, 3-trifluoromethoxybenzyl group, 4-trifluoromethoxy Group, 2-pentafluoroethoxybenzyl group, 3-pentafluoroethoxybenzyl group, 4-pentafluoroethoxybenzyl group, 2- (2-trifluoromethylphenyl) ethyl group, 2- (3-trifluoromethylphenyl) Ethyl group, 2- (4-trifluoromethylphenyl) ethyl group, 2- (2-trifluoromethoxyphenyl) ethyl group, 2- (3-trifluoromethoxyphenyl) ethyl group, 2- (4-trifluoromethoxy) Phenyl) ethyl group, 2- (2-pentafluoroethoxyphenyl) ethyl group, 2- (3-pentafluoroethoxyphenyl) ethyl group, 2- (4-pentafluoroethoxyphenyl) ethyl group, 3- (2-triphenyl) ethyl group Fluoromethylphenyl) propyl group, 3- (3-trifluoromethylphenyl) group Pill group, 3- (4-trifluoromethylphenyl) propyl group, 3- (2-trifluoromethoxyphenyl) propyl group, 3- (3-trifluoromethoxyphenyl) propyl group, 3- (4-trifluoromethoxy) Phenyl) propyl group, 3- (3-pentafluoroethoxyphenyl) propyl group, 3- (4-pentafluoroethoxyphenyl) propyl group, 4- (3-pentafluoroethoxyphenyl) butyl group, 5- (4-tri- Fluoromethylphenyl) pentyl group, 4- (4-trifluoromethylphenyl) pentyl group, 4- (4-trifluoromethoxyphenyl) pentyl group, 6- (3-trifluoromethylphenyl) hexyl group, 6- (4) -Trifluoromethylphenyl) hexyl group, 6- (4-trifluoromethoxyphenyl) A hexyl group etc. can be mentioned.

  [Piperazinyl group [in the piperazine ring, at least one phenyl C.sub.1-6 alkyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6. And the like.] May be substituted, for example, 1-piperazinyl group, 2-piperazinyl group, 3,4-dibenzyl) -1-piperazinyl group, 2,3,4-tribenzyl-1-piperazinyl group, 4-benzyl-1-piperazinyl group, 4- (2-phenethyl) -1-piperazinyl group, 4- (3-phenylpropyl)- 1-piperazinyl group, 4- (4-phenylbutyl) -1-piperazinyl group, 4- (5-phenylpentyl) -1-piperazinyl group, 4- (6- (6-phenyl) Phenylhexyl) -1-piperazinyl group, 4- (2-fluorobenzyl) -1-piperazinyl group, 4- (3-fluorobenzyl) -1-piperazinyl group, 4- (4-fluorobenzyl) -1-piperazinyl group, 4- (2-chlorobenzyl) -1-piperazinyl group, 4- (3-chlorobenzyl) -1-piperazinyl group, 4- (4-chlorobenzyl) -1-piperazinyl group, 4- (2,3-dichloromethane) Benzyl) -1-piperazinyl group, 4- (2,4-dichlorobenzyl) -1-piperazinyl group, 4- (3,4-dichlorobenzyl) -1-piperazinyl group, 4- (3,5-dichlorobenzyl) -1-piperazinyl group, 4- (3,4,5-trichlorobenzyl) -1-piperazinyl group, 4- (2,3,4,5,6-pentafluorobenzyl) -1- Perazinyl group, 4- (2-trifluoromethylbenzyl) -1-piperazinyl group, 4- (3-trifluoromethylbenzyl) -1-piperazinyl group, 4- (4-trifluoromethylbenzyl) -1-piperazinyl group 4- (4-methylbenzyl) -1-piperazinyl group, 4- (3,4-dimethylbenzyl) -1-piperazinyl group, 4- (2,4,6-trimethylbenzyl) -1-piperazinyl group, 4 -(2-Pentafluoroethyl benzyl) -1-piperazinyl group, 4- (3-pentafluoroethyl benzyl) -1-piperazinyl group, 4- (4-pentafluoroethyl benzyl) -1-piperazinyl group, 4- (4- 2-trifluoromethoxybenzyl) -1-piperazinyl group, 4- (3-trifluoromethoxybenzyl) -1-piperazinyl group, 4- (4-trifluoromethoxybenzyl) -1-piperazinyl group, 4- (4-methoxybenzyl) -1-piperazinyl group, 4- (3,4-dimethoxybenzyl) -1-piperazinyl group, 4- (2 , 4,6-trimethoxybenzyl) -1-piperazinyl group, 4- (2-pentafluoroethoxybenzyl) -1-piperazinyl group, 4- (3-pentafluoroethoxybenzyl) -1-piperazinyl group, 4- (4- 4-pentafluoroethoxybenzyl) -1-piperazinyl group, 4- [2- (4-trifluoromethoxyphenyl) ethyl] -1-piperazinyl group, 4- [3- (4-trifluoromethoxyphenyl) propyl]- 1-piperazinyl group, 4- [4- (4-trifluoromethoxyphenyl) butyl] -1-piperazinyl group, 4- [5- (4) Trifluoromethoxyphenyl) pentyl] -1-piperazinyl group, 4- [6- (4-trifluoromethoxyphenyl) hexyl] -1-piperazinyl group, 4- [2- (4-trifluoromethylphenyl) ethyl]- 1-piperazinyl group, 4- [3- (4-trifluoromethylphenyl) propyl] -1-piperazinyl group, 4- [4- (4-trifluoromethylphenyl) butyl] -1-piperazinyl group, 4- [4 Piperazinyl groups such as 5- (4-trifluoromethylphenyl) pentyl] -1-piperazinyl group, 4- [6- (4-trifluoromethylphenyl) hexyl] -1-piperazinyl group, etc. ~ 3 phenyl C 1-6 alkyl groups (on the phenyl ring, halogen atoms, halogen substituted or unsubstituted C 1-6 alkyl And 1 to 5, preferably 1 to 3 groups selected from the group consisting of halogen-substituted or unsubstituted C1-6 alkoxy groups may be substituted). Can.

The piperidyl group [a piperidine ring is an amino group (an amino group is a phenyl group [a phenyl group is a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1 At least one group selected from the group consisting of 6 alkoxy groups may be substituted], and at least one group selected from the group consisting of a C1-6 alkyl group may be substituted), A phenoxy group (in which at least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group is substituted on a phenyl ring; And phenyl C1-6 alkyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halo At least one group selected from the group consisting of at least one group selected from the group consisting of substituted or unsubstituted C.sub.1-6 alkoxy groups may be substituted) And the like.] Is, for example, 1-piperidyl group, 2-piperidyl group, 3-piperidyl group, 4-piperidyl group, 2,4-) Diamino-1-piperidyl group, 2,4,6-triamino-1-piperidyl group, 2-amino-1-piperidyl group, 3-amino-1-piperidyl group, 4-amino-1-piperidyl group, 4-methyl Amino-1-piperidyl group, 4-ethylamino-1-piperidyl group, 4-n-propylamino-1-piperidyl group, 4-dimethylamino-1-piperidyl group, 4-diethylamino-1-piperidyl group Group, 4-di-n-propylamino-1-piperidyl group, 4-phenylamino-1-piperidyl group, 4- (N-phenyl-N-methylamino) -1-piperidyl group, 4- (2-) Fluorophenylamino) -1-piperidyl group, 4- (3-fluorophenylamino) -1-piperidyl group, 4- (4-fluorophenylamino) -1-piperidyl group, 4- (2-chlorophenylamino) -1 -Piperidyl group, 4- (3-chlorophenylamino) -1-piperidyl group, 4- (4-chlorophenylamino) -1-piperidyl group, 4- (2,3-dichlorophenylamino) -1-piperidyl group, 4- (2,4,6-trifluorophenylamino) -1-piperidyl group, 4- (2,4-dichlorophenylamino) -1-piperidyl group, 4- (3,4-diqu) Rolophenylamino) -1-piperidyl group, 4- (3,5-dichlorophenylamino) -1-piperidyl group, 4- (2,3,4,5,6-pentafluorophenylamino) -1-piperidyl group, 4- (2-trifluoromethylphenylamino) -1-piperidyl group, 4- (2-methylphenylamino) -1-piperidyl group, 4- (2,3-dimethylphenylamino) -1-piperidyl group, 4 -(2-trifluoromethylphenylamino) -1-piperidyl group, 4- (2,4,6-trimethylphenylamino) -1-piperidyl group, 4- (4-trifluoromethylphenylamino) -1-piperidyl Group, 4- (2-pentafluoroethylphenylamino) -1-piperidyl group, 4- (3-pentafluoroethylphenylamino) -1-piperidine Group, 4- (4-pentafluoroethylphenylamino) -1-piperidyl group, 4- (2-trifluoromethoxyphenylamino) -1-piperidyl group, 4- (2-methoxyphenylamino) -1-piperidyl group 4- (2,3-dimethoxyphenylamino) -1-piperidyl group, 4- (2,4,6-trimethoxyphenylamino) -1-piperidyl group, 4- [N-methyl-N- (2, 4,6-Trimethoxyphenylamino)]-1-piperidyl group, 4- [N-methyl-N- (3,4-dimethylphenylamino)]-1-piperidyl group, 4- (3-trifluoromethoxyphenyl) Amino) -1-piperidyl group, 4- (4-trifluoromethoxyphenylamino) -1-piperidyl group, 4- (2-pentafluoroethoxyphenylamino) -1 Piperidyl group, 4- (3-pentafluoroethoxyphenylamino) -1-piperidyl group, 4- (4-pentafluoroethoxyphenylamino) -1-piperidyl group, 4-phenoxy-1-piperidyl group, 2,4- Diphenoxy-1-piperidyl group, 2,4,6-triphenoxy-1-piperidyl group, 2- (2-fluorophenoxy) -1-piperidyl group, 3- (3-fluorophenoxy) -2-piperidyl group, 4 -(4-Fluorophenoxy) -3-piperidyl group, 2- (2-chlorophenoxy) -4-piperidyl group, 3- (3-chlorophenoxy) -5-piperidyl group, 4- (4-chlorophenoxy)- 2-piperidyl group, 5- (2-bromophenoxy) -2-piperidyl group, 6- (3-bromophenoxy) -3-piperidyl group, 4- ( 4-bromophenoxy) -1-piperidyl group, 3- (2,3-dichlorophenoxy) -2-piperidyl group, 4- (3,4-dichlorophenoxy) -3-piperidyl group, 3- (2,4-) Dichlorophenoxy) -4-piperidyl group, 2- (3,4,5-trichlorophenoxy) -3-piperidyl group, 6- (2,4,6-trichlorophenoxy) -2-piperidyl group, 3- (2, 3,4,5,6-pentafluorophenoxy) -1-piperidyl group, 4- (2-methylphenoxy) -1-piperidyl group, 5- (3-methylphenoxy) -2-piperidyl group, 6- (4) -Methylphenoxy) -3-piperidyl group, 1- (2-ethyl phenoxy) -4-piperidyl group, 2- (3-ethyl phenoxy) -1-piperidyl group, 3- (4-ethyl phenoxy) group 2-piperidyl group, 4- (4-n-propylphenoxy) -3-piperidyl group, 3- (4-tert-butylphenoxy) -4-piperidyl group, 2- (4-n-butylphenoxy) -3- Piperidyl group, 1- (2-trifluoromethylphenoxy) -2-piperidyl group, 2- (3-trifluoromethylphenoxy) -1-piperidyl group, 3- (4-trifluoromethylphenoxy) -1-piperidyl group 1- (2-pentafluoroethyl phenoxy) -4-piperidyl group, 1- (3-pentafluoroethyl phenoxy) -4-piperidyl group, 4- (2,3-dimethylphenoxy) -1-piperidyl group, 1 -(3,4,5-trimethylphenoxy) -4-piperidyl group, 1- (4-n-pentylphenoxy) -4-piperidyl group, 4- (4- -Hexylphenoxy) -1-piperidyl group, 4- (2-methoxyphenoxy) -1-piperidyl group, 1- (3-methoxyphenoxy) -4-piperidyl group, 1- (4-methoxyphenoxy) -4-piperidyl Group, 2- (2-ethoxyphenoxy) -3-piperidyl group, 3- (3-ethoxyphenoxy) -4-piperidyl group, 4- (4-ethoxyphenoxy) -3-piperidyl group, 3- (4-n) -Propoxyphenoxy) -2-piperidyl group, 2- (4-tert-butoxyphenoxy) -1-piperidyl group, 1- (4-n-butoxyphenoxy) -2-piperidyl group, 2- (2-trifluoromethoxy) group Phenoxy) -3-piperidyl group, 3- (3-trifluoromethoxyphenoxy) -4-piperidyl group, 4- (4-trifluoromethoxy) Phenoxy) -3-piperidyl group, 3- (2-pentafluoroethoxyphenoxy) -2-piperidyl group, 2- (4-pentafluoroethoxyphenoxy) -1-piperidyl group, 1- (2,3-dimethoxyphenoxy) group -4-piperidyl group, 4- (3,4,5-trimethoxyphenoxy) -1-piperidyl group, 4- (4-n-pentyloxyphenoxy) -1-piperidyl group, 4- (4-n-hexyl) group Oxyphenoxy) -1-piperidyl group, 4-benzyl-1-piperidyl group, 2,4-dibenzyl-1-piperidyl group, 2,4,6-tribenzyl-1-piperidyl group, 2- (2-fluorobenzyl) -1-piperidyl group, 3- [2- (3-fluorophenyl) ethyl] -2-piperidyl group, 4- [1- (4-fluorophenyl) ethyl]- -Piperidyl group, 2- [3- (2-chlorophenyl) propyl] -4-piperidyl group, 3- [4- (3-chlorophenyl) butyl] -5-piperidyl group, 4- [5- (4-chlorophenyl) group Pentyl] -2-piperidyl group, 5-([6- (2-bromophenyl) hexyl] -2-piperidyl group, 6- (3-bromobenzyl) -3-piperidyl group, 4- (4-bromobenzyl) -1-piperidyl group, 3- (2,3-dichlorobenzyl) -2-piperidyl group, 4- (3,4-dichlorobenzyl) -3-piperidyl group, 3- (2,4-dichlorobenzyl) -4 -Piperidyl group, 2- (3,4,5-trichlorobenzyl) -3-piperidyl group, 6- (2,4,6-trichlorobenzyl) -2-piperidyl group, 3- (2,3,4,5 , 6-pentaful Lobenzyl) -1-piperidyl group, 4- (2-methylbenzyl) -1-piperidyl group, 5- [2- (3-methylphenyl) ethyl] -2-piperidyl group, 6- [3- (4-methyl) group Phenyl) propyl] -3-piperidyl group, 1- [4- (2-ethylphenyl) butyl] -4-piperidyl group, 2- [5- (3-ethylphenyl) pentyl] -1-piperidyl group, 3- [6- (4-ethylphenyl) hexyl] -2-piperidyl group, 4- (4-n-propylbenzyl) -3-piperidyl group, 3- (4-tert-butylbenzyl) -4-piperidyl group, 2 -(4-n-butylbenzyl) -3-piperidyl group, 1- (2-trifluoromethylbenzyl) -2-piperidyl group, 2- (3-trifluoromethylbenzyl) -1-piperidyl group, 3- ( 4 -Trifluoromethylbenzyl) -1-piperidyl group, 1- (2-pentafluoroethylbenzyl) -4-piperidyl group, 1- (3-pentafluoroethylbenzyl) -4-piperidyl group, 4- (2,3 -Dimethylbenzyl) -1-piperidyl group, 1- (3,4,5-trimethylbenzyl) -4-piperidyl group, 1- (4-n-pentylbenzyl) -4-piperidyl group, 4- (4-n) -Hexylbenzyl) -1-piperidyl group, 4- (2-methoxybenzyl) -1-piperidyl group, 1- [2- (3-methoxyphenyl) ethyl] -4-piperidyl group, 1- [1- (4) -Methoxyphenyl) ethyl] -4-piperidyl group, 2- [3- (2-ethoxyphenyl) propyl] -3-piperidyl group, 3- [4- (3-ethoxyphenyl) butyl] -4 Piperidyl group, 4- [5- (4-ethoxyphenyl) pentyl] -3-piperidyl group, 3- [6- (4-n-propoxyphenyl) hexyl-2-piperidyl group, 2- (4-tert-butoxy group Benzyl) -1-piperidyl group, 1- (4-n-butoxybenzyl) -2-piperidyl group, 2- (2-trifluoromethoxybenzyl) -3-piperidyl group, 3- (3-trifluoromethoxybenzyl) -4-piperidyl group, 4- (4-trifluoromethoxybenzyl) -3-piperidyl group, 3- (2-pentafluoroethoxybenzyl) -2-piperidyl group, 2- (4-pentafluoroethoxybenzyl) -1 -Piperidyl group, 1- (2,3-dimethoxybenzyl) -4-piperidyl group, 4- (3,4,5-trimethoxybenzyl) -1-pipe Dyl, 4- (4-n-pentyloxybenzyl) -1-piperidyl group, 4- (4-n-hexyloxybenzyl) -1-piperidyl group, 4-benzyl-3-phenoxy-1-piperidyl group, Piperidyl groups such as 4-phenoxy-2-methylamino-1-piperidyl group [an amino group (on the piperidine ring, a phenyl group on the amino group, a halogen atom on the phenyl ring, halogen substituted or unsubstituted 1 to 5, preferably 1 to 3 groups selected from the group consisting of C1-6 alkyl groups of the above and halogen-substituted or unsubstituted C1-6 alkoxy groups] and C1-6 alkyl A group selected from the group consisting of 1 to 2 groups, which may be substituted by 1 to 2), a phenoxy group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and And 1 to 5, preferably 1 to 3 groups selected from the group consisting of halogen-substituted or unsubstituted C1-6 alkoxy groups, and phenyl C1-6 alkyl groups (on the phenyl ring) A halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and


1 to 5, preferably 1 to 3 groups selected from the group consisting of rogen-substituted or unsubstituted C1 to 6 alkoxy groups may be selected from 1 to 3) And the like] may be mentioned.

  A pyrrolyl group [on the pyrrole ring, a C1-6 alkyl group and a phenyl C1-6 alkyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1 -At least one kind of group selected from the group consisting of a group selected from the group consisting of -6 alkoxy group may be substituted], for example, 1-, 2- or 3-) pyrrolyl, 1- (4-trifluoromethoxybenzyl)-(2- or 3-) pyrrolyl, 1- (4-trifluoromethylbenzyl)-(2- or 3-) pyrrolyl 1- (4-chlorobenzyl)-(2- or 3-) pyrrolyl, 1- (4-methoxybenzyl)-(2- or 3-) pyrrolyl, 1- (4-methylbenzyl)-(2- or -) Pyrrolyl, 1- (3,4-dimethoxybenzyl)-(2- or 3-) pyrrolyl, 1- (2,4,6-trimethoxybenzyl)-(2- or 3-) pyrrolyl, 1-(-) 3,4-Dimethylbenzyl)-(2- or 3-) pyrrolyl, 1- (2,4,6-trimethylbenzyl)-(2- or 3-) pyrrolyl, 1- (2,4,6-trifluoro) Benzyl)-(2- or 3-) pyrrolyl, 1- (2,6-dichlorobenzyl)-(2- or 3-) pyrrolyl, 1-benzyl- (2- or 3-) pyrrolyl, 1,2-dibenzyl -(3-, 4- or 5-) pyrrolyl, 1,2,4-tribenzyl- (3- or 5-) pyrrolyl, 2- (3-chloro-4-trifluoromethoxybenzyl)-(1-, 3) -, 4- or 5-) pyrrolyl, 1-methyl- (2- or 3-) pi Ryl, 1-ethyl- (2- or 3-) pyrrolyl, 1-n-propyl- (2- or 3-) pyrrolyl, 1-n-butyl- (2- or 3-) pyrrolyl, 1-n-pentyl -(2- or 3-) pyrrolyl, 1-n-hexyl- (2- or 3-) pyrrolyl, 1,3-dimethyl- (2-, 4- or 5-) pyrrolyl, 1,3,4-trimethyl Pyrrolyl group such as-(2- or 5-) pyrrolyl, 1-benzyl-3-methyl- (2-, 4- or 5-) pyrrolyl group [C1-6 alkyl group and alkyl moiety are present on the pyrrole ring A phenyl C1-6 alkyl group which is a linear or branched alkyl group having 1 to 6 carbon atoms (a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted group on the phenyl ring Selected from the group consisting of C1-6 alkoxy groups of And the group selected from the group consisting of 1 to 5 and preferably 1 to 3 substituted groups may be substituted).

  Phenylthio group (on the phenyl ring, at least one of a group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group is substituted. For example, from the group consisting of unsubstituted phenylthio groups and the halogen atoms as defined above, halogen-substituted or unsubstituted C.sub.1-6 alkyl groups and halogen-substituted or unsubstituted C.sub.1-6 alkoxy groups. A phenylthio group having 1 to 5, preferably 1 to 3 selected substituents, such as phenylthio group, 2-fluorophenylthio group, 3-fluorophenylthio group, 4-fluorophenylthio group, 2-chlorophenylthio group, 3-chlorophenylthio group, 4-chlorophenylthio group, 2-bromophenyl O group, 3-bromophenylthio group, 4-bromophenylthio group, 2-iodophenylthio group, 3-iodophenylthio group, 4-iodophenylthio group, 2,3-difluorophenylthio group, 3,4 -Difluorophenylthio group, 3,5-difluorophenylthio group, 2,4-difluorophenylthio group, 2,6-difluorophenylthio group, 2,3-dichlorophenylthio group, 3,4-dichlorophenylthio group, 3 5-dichlorophenylthio group, 2,4-dichlorophenylthio group, 2,6-dichlorophenylthio group, 3,4,5-trifluorophenylthio group, 3,4,5-trichlorophenylthio group, 2,4,4, 6-trifluorophenylthio group, 2,4,6-trichlorophenylthio group, 2-fluoro-4-bromophenylthio group, 4 Chloro-3-fluorophenylthio group, 2,3,4-trichlorophenylthio group, 2,3,4,5,6-pentafluorophenylthio group, 2,4,6-trimethylphenylthio group, 4-n -Butylphenylthio group, 2,4-dimethylphenylthio group, 2,3-dimethylphenylthio group, 2,6-dimethylphenylthio group, 3,5-dimethylphenylthio group, 2,5-dimethylphenylthio group 3,5-ditrifluoromethylphenylthio group, 4-n-butoxyphenylthio group, 2,4-dimethoxyphenylthio group, 2,3-dimethoxyphenylthio group, 2,6-dimethoxyphenylthio group, 3, 5-dimethoxyphenylthio group, 2,5-dimethoxyphenylthio group, 2,4,6-trimethoxyphenylthio group, 3,5-ditrifluoromethoxy group Siphenylthio group, 3-chloro-4-methoxyphenylthio group, 2-chloro-4-trifluoromethoxyphenylthio group, 3-methyl-4-fluorophenylthio group, 4-bromo-3-trifluoromethylphenylthio group , 2-methylphenylthio group, 3-methylphenylthio group, 4-methylphenylthio group, 2-methyl-3-chlorophenylthio group, 3-methyl-4-chlorophenylthio group, 2-chloro-4-methylphenyl Thio group, 2-methyl-3-fluorophenylthio group, 2-trifluoromethylphenylthio group, 3-trifluoromethylphenylthio group, 4-trifluoromethylphenylthio group, 2-pentafluoroethylphenylthio group, 3-pentafluoroethylphenylthio group, 4-pentafluoroethylphenylthio group, -Isopropylphenylthio group, 3-isopropylphenylthio group, 4-isopropylphenylthio group, 2-tert-butylphenylthio group, 3-tert-butylphenylthio group, 4-tert-butylphenylthio group, 2-sec -Butylphenylthio group, 3-sec-butylphenylthio group, 4-sec-butylphenylthio group, 2-n-heptafluoropropylphenylthio group, 3-n-heptafluoropropylphenylthio group, 4-n- Heptafluoropropylphenylthio group, 4-pentylphenylthio group, 4-hexylphenylthio group, 2-methoxyphenylthio group, 3-methoxyphenylthio group, 4-methoxyphenylthio group, 3-chloro-2-methoxyphenyl group Thio group, 2-fluoro-3-methoxyphenylthio group, -Fluoro-4-methoxyphenylthio group, 2,3,4-trifluorophenylthio group, 2-trifluoromethoxyphenylthio group, 3-trifluoromethoxyphenylthio group, 4-trifluoromethoxyphenylthio group, 3 -Fluoro-2-trifluoromethoxyphenylthio group, 2-fluoro-3-trifluoromethoxyphenylthio group, 3-fluoro-4-trifluoromethoxyphenylthio group, 3-chloro-2-trifluoromethoxyphenylthio group , 2-chloro-3-trifluoromethoxyphenylthio group, 3-chloro-4-trifluoromethoxyphenylthio group, 2-pentafluoroethoxyphenylthio group, 3-pentafluoroethoxyphenylthio group, 4-pentafluoroethoxy Phenylthio group, 3-chloro-2-penta Fluoroethoxyphenylthio group, 2-chloro-3-pentafluoroethoxyphenylthio group, 3-chloro-4-pentafluoroethoxyphenylthio group, 2-isopropoxyphenylthio group, 3-isopropoxyphenylthio group, 4- Isopropoxyphenylthio group, 2-tert-butoxyphenylthio group, 3-tert-butoxyphenylthio group, 4-tert-butoxyphenylthio group, 2-sec-butoxyphenylthio group, 3-sec-butoxyphenylthio group 4-sec-butoxyphenylthio group, 2-n-heptafluoropropoxyphenylthio group, 3-n-heptafluoropropoxyphenylthio group, 4-n-heptafluoropropoxyphenylthio group, 4-n-pentoxyphenyl Thio group, 4-n-hexyloxyf Niruchio group, and the like can be mentioned.

A benzothiazolyloxy group (on the benzothiazole ring, a (b-1) phenyl group [on a phenyl ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1 To 6 alkoxy groups, at least one of a group selected from the group consisting of an alkoxy group may be substituted], (b-2) piperazinyl group [on a piperazine ring, a phenyl C.sub.1-6 alkyl group (on a phenyl ring At least one of a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group may be substituted), phenyl A C 2-6 alkenyl group (on the phenyl ring, it comprises a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group And at least one of the groups selected from the group may be substituted) and a phenyl group (on the phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1 At least one group selected from the group consisting of -6 alkoxy groups may be substituted), and at least one group selected from the group consisting of-6 alkoxy group may be substituted], (b-3) piperidyl Group [a piperidine ring, an amino group (an amino group, a phenyl group [a phenyl group, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 At least one group selected from the group consisting of an alkoxy group may be substituted] and at least one group selected from the group consisting of a C1-6 alkyl group may be substituted), pheno (In the phenyl ring, at least one of a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group is substituted And phenyl C1-6 alkyl group (on the phenyl ring, selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group At least one kind of the aforementioned groups may be substituted), and at least one kind of the group selected from the group consisting of (a) may be substituted], (b-4) pyrrolyl group [on the pyrrole ring, C1-6 alkyl groups and phenyl C1-6 alkyl groups (on the phenyl ring, halogen atoms, halogen substituted or unsubstituted C1-6 alkyl groups and halogen substitution And at least one group selected from the group consisting of at least one group selected from the group consisting of unsubstituted C1-6 alkoxy groups may be substituted) And (b-5) phenylthio group [in the phenyl ring, a group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group] As at least one group selected from the group consisting of at least one group optionally substituted, at least one group may be substituted), for example, a 2-benzothiazolyloxy group, 4-benzothiazole group Roxy group, 5-benzothiazolyloxy group, 6-benzothiazolyloxy group, 7-benzothiazolyloxy group, 2- (1-piperazinyl) -4-benzothiazolyloxy group, 2- (4-Benji Le-1-piperazinyl) -4-benzothiazolyloxy group, 2- (3,4-dibenzyl-1-piperazinyl) -4-benzothiazolyloxy group, 5- (2,3,4-tribenzyl- 1-piperazinyl) -2-benzothiazolyloxy group, 4- [4- (2-phenethyl) -1-piperazinyl] -2-benzothiazolyloxy group, 4- [4- (3-phenylpropyl) group -1-piperazinyl] -5-benzothiazolyloxy group, 4- [4- (4-phenylbutyl) -1-piperazinyl] -6-benzothiazolyloxy group, 4- [4- (5-phenyl) group Pentyl) -1-piperazinyl] -7-benzothiazolyloxy group, 2- [4- (6-phenylhexyl) -1-piperazinyl] -4-benzothiazolyloxy group, 4- [4- (2) -Fluorobenzyl -1-piperazinyl] -2-benzothiazolyloxy group, 2- [4- (3-fluorobenzyl) -1-piperazinyl] -4-benzothiazolyloxy group, 2- [4- (4-fluoro) Benzyl) -1-piperazinyl] -5-benzothiazolyloxy group, 2- [4- (2-chlorobenzyl) -1-piperazinyl] -6-benzothiazolyloxy group, 2- [4- (3) -Chlorobenzyl) -1-piperazinyl] -7-benzothiazolyloxy group, 5- [4- (4-chlorobenzyl) -1-piperazinyl] -4-benzothiazolyloxy group, 6- [4- (2,3-Dichlorobenzyl) -1-piperazinyl] -4-benzothiazolyloxy group, 7- [4- (2,4-dichlorobenzyl) -1-piperazinyl] -4-benzothiazolyloxy group , 2- [4 (3,4-Dichlorobenzyl) -1-piperazinyl] -4-benzothiazolyloxy group, 4- [4- (3,5-dichlorobenzyl) -1-piperazinyl] -2-benzothiazolyloxy group , 4- [4- (3,4,5-trichlorobenzyl) -1-piperazinyl] -5-benzothiazolyloxy group, 4- [4- (2,3,4,5,6-pentafluorobenzyl) ) -L-Piperazinyl] -2-benzothiazolyloxy group, 4- [4- (2-trifluoromethylbenzyl) -1-piperazinyl] -6-benzothiazolyloxy group, 4- [4- (4- 3-trifluoromethylbenzyl) -1-piperazinyl] -7-benzothiazolyloxy group, 2- [4- (4-trifluoromethylbenzyl) -1-piperazinyl] -4-benzothiazolyloxy group, 5- [4- (4-Methylbenzyl) -1-piperazinyl] -4-benzothiazolyloxy group, 6- [4- (3,4-dimethylbenzyl) -1-piperazinyl] -4-benzothiazolyloxy Group, 7- [4- (2,4,6-trimethylbenzyl) -1-piperazinyl] -4-benzothiazolyloxy group, 4- [4- (2-pentafluoroethylbenzyl) -1-piperazinyl] -2-benzothiazolyloxy group, 4- [4- (3-pentafluoroethyl benzyl) -1-piperazinyl] -5-benzothiazolyloxy group, 4- [4- (4-pentafluoroethyl benzyl] group ) -1-Piperazinyl] -6-benzothiazolyloxy group, 4- [4- (2-trifluoromethoxybenzyl) -1-piperazinyl] -7-benzothiazolyloxy group, 5- [4 (3-Trifluoromethoxybenzyl) -1-piperazinyl] -4-benzothiazolyloxy group, 6- [4- (4-trifluoromethoxybenzyl) -1-piperazinyl] -5-benzothiazolyloxy group 7- [4- (4-methoxybenzyl) -1-piperazinyl] -5-benzothiazolyloxy group, 6- [4- (3,4-dimethoxybenzyl) -1-piperazinyl] -4-benzothia Zoryloxy group, 7- [4- (2,4,6-trimethoxybenzyl) -1-piperazinyl] -4-benzothiazolyloxy group, 5- [4- (2-pentafluoroethoxybenzyl)- 1-piperazinyl] -4-benzothiazolyloxy group, 4- [4- (3-pentafluoroethoxybenzyl) -1-piperazinyl] -2-benzothiazolyloxy group, 6 [4- (4-Pentafluoroethoxybenzyl) -1-piperazinyl] -4-benzothiazolyloxy group, 4- {4- [2- (4-trifluoromethoxyphenyl) ethyl] -1-piperazinyl}- 2-benzothiazolyloxy group, 4- {4- [3- (4-trifluoromethoxyphenyl) propyl] -1-piperazinyl} -2-benzothiazolyloxy group, 4- {4- [4-] (4-Trifluoromethoxyphenyl) butyl] -1-piperazinyl} -2-benzothiazolyloxy group, 4- {4- [5- (4-trifluoromethoxyphenyl) pentyl] -1-piperazinyl} -2 -Benzothiazolyloxy group, 4- {4- [6- (4-trifluoromethoxyphenyl) hexyl] -1-piperazinyl} -2-benzothiazolyloxy group, 4- {4- [2- (4-Trifluoromethylphenyl) ethyl] -1-piperazinyl} -2-benzothiazolyloxy group, 5- {4- [3- (4-trifluoromethylphenyl) propyl]- 1-piperazinyl} -2-benzothiazolyloxy group, 6- {4- [4- (4-trifluoromethylphenyl) butyl] -1-piperazinyl} -2-benzothiazolyloxy group, 7- { 4- [5- (4-trifluoromethylphenyl) pentyl] -1-piperazinyl} -2-benzothiazolyloxy group, 5- {4- [6- (4-trifluoromethylphenyl) hexyl] -1 -Piperazinyl} -2-benzothiazolyloxy group, 2- [4- (trifluoromethoxyphenoxy-1-piperidyl)]-6-benzothiazolyloxy group, 2- [4- (trifluro] Lomethoxybenzyl-1-piperidyl)]-6-benzothiazolyloxy group, 2- {4- [N-ethyl-N- (4-chlorophenyl) amino] -1-piperidyl} -6-benzothiazolyl Oxy group, 2-phenyl-5-benzothiazolyloxy group, 2- (4-chlorophenyl) -5-benzothiazolyloxy group, 2- (4-trifluoromethoxyphenyl) -6-benzothiazolyl Oxy group, 2- (3-trifluoromethylphenyl) -5-benzothiazolyloxy group, 2- (1-piperidyl) -4-benzothiazolyloxy group, 2- (4-benzyl-1-piperidyl) ) 4-benzothiazolyloxy group, 2- (3,4-dibenzyl-1-piperidyl) -4-benzothiazolyloxy group, 5- (2,3,4-tribenzyl-1-piperidyl) -2-benzothiazolyloxy group, 4- [4- (2-phenethyl) -1-piperidyl] -2-benzothiazolyloxy group, 4- [4- (3-phenylpropyl) -1-piperidyl ] 5-benzothiazolyloxy group, 4- [4- (4-phenylbutyl) -1-piperidyl] -6-benzothiazolyloxy group, 4- [4- (5-phenylpentyl) -1 -Piperidyl] -7-benzothiazolyloxy group, 2- [4- (6-phenylhexyl) -1-piperidyl) -4-benzothiazolyloxy group, 4- [4- (2-fluorobenzyl) group -1-piperidyl] -2-benzothiazolyloxy group, 2- [4- (3-fluorobenzyl) -1-piperidyl] -4-benzothiazolyloxy group, 2- [4- (4-fluoro) Benzyl) -1-piperazinyl] -5-benzothiazolyloxy group, 2- [4- (2-chlorobenzyl) -1-piperidyl] -6-benzothiazolyloxy group, 2- [4- (3-chlorobenzyl) -1-] Piperidyl] -7-benzothiazolyloxy, 5- [4- (4-chlorobenzyl) -1-piperidyl] -4-benzothiazolyloxy, 6- [4- (2,3-dichlorobenzyl) )-1-Piperidyl] -4-benzothiazolyloxy group, 7- [4- (2,4-dichlorobenzyl) -1-piperidyl] -4-benzothiazolyloxy group, 2- [4- (4) 3,4-Dichlorobenzyl) -1-piperidyl] -4-benzothiazolyloxy group, 4- [4- (3,5-dichlorobenzyl) -1-piperidyl] -2-benzothiazolyloxy group, 4- [4- (3,4,5-trichloromethane Jyl) -1-piperidyl] -5-benzothiazolyloxy group, 4- [4- (2,3,4,5,6-pentafluorobenzyl) -1-piperidyl] -2-benzothiazolyloxy Group, 4- [4- (2-trifluoromethylbenzyl) -1-piperidyl] -6-benzothiazolyloxy group, 4- [4- (3-trifluoromethylbenzyl) -1-piperidyl] -7 -Benzothiazolyloxy group, 2- [4- (4-trifluoromethylbenzyl) -1-piperidyl] -4-benzothiazolyloxy group, 5- [4- (4-methylbenzyl) -1-] Piperidyl] -4-benzothiazolyloxy, 6- [4- (3,4-dimethylbenzyl) -1-piperidyl] -4-benzothiazolyloxy, 7- [4- (2,4,5 6-trimethylbenzyl) -1- Peridyl] -4-benzothiazolyloxy group, 4- [4- (2-pentafluoroethylbenzyl) -1-piperidyl] -2-benzothiazolyloxy group, 4- [4- (3-pentafluoro] Ethyl benzyl) -1-piperidyl] -5-benzothiazolyloxy


Group, 4- [4- (4-pentafluoroethyl benzyl) -1-piperidyl] -6-benzothiazolyloxy group, 4- [4- (2-trifluoromethoxybenzyl) -1-piperidyl] -7 -Benzothiazolyloxy group, 5- [4- (3-trifluoromethoxybenzyl) -1-piperidyl] -4-benzothiazolyloxy group, 6- [4- (4-trifluoromethoxybenzyl)- 1-piperidyl] -5-benzothiazolyloxy group, 7- [4- (4-methoxybenzyl) -1-piperidyl] -5-benzothiazolyloxy group, 6- [4- (3,4-) Dimethoxybenzyl) -1-piperidyl] -4-benzothiazolyloxy group, 7- [4- (2,4,6-trimethoxybenzyl) -1-piperidyl] -4-benzothiazolyloxy group, 5 -[4 (2-Pentafluoroethoxybenzyl) -1-piperidyl] -4-benzothiazolyloxy group, 4- [4- (3-pentafluoroethoxybenzyl) -1-piperidyl] -2-benzothiazolyloxy group , 6- [4- (4-pentafluoroethoxybenzyl) -1-piperidyl] -4-benzothiazolyloxy group, 4- {4- [2- (4-trifluoromethoxyphenyl) ethyl] -1- Piperidyl} -2-benzothiazolyloxy group, 4- {4- [3- (4-trifluoromethoxyphenyl) propyl] -1-piperidyl} -2-benzothiazolyloxy group, 4- {4- [4- (4-Trifluoromethoxyphenyl) butyl] -1-piperidyl} -2-benzothiazolyloxy group, 4- {4- [5- (4-trifluoromethoxypheny] ) Pentyl] -1-piperidyl} -2-benzothiazolyloxy group, 4- {4- [6- (4-trifluoromethoxyphenyl) hexyl] -1-piperidyl} -2-benzothiazolyloxy group , 4- {4- [2- (4-trifluoromethylphenyl) ethyl] -1-piperidyl} -2-benzothiazolyloxy group, 5- {4- [3- (4-trifluoromethylphenyl) group Propyl] -1-piperidyl} -2-benzothiazolyloxy group, 6- {4- [4- (4-trifluoromethylphenyl) butyl] -1-piperidyl} -2-benzothiazolyloxy group, 7- {4- [5- (4-trifluoromethylphenyl) pentyl] -1-piperidyl} -2-benzothiazolyloxy group, 5- {4- [6- (4-trifluoromethylphenyl) hexy] [L] -Piperidyl} -2-benzothiazolyloxy group, 2- (4-phenoxy-1-piperidyl) -4-benzothiazolyloxy group, 2- (3,4-diphenoxy-1-piperidyl) ) 4-benzothiazolyloxy group, 5- (2,3,4-triphenoxy-1-piperidyl) -2-benzothiazolyloxy group, 4- [4- (2-fluorophenoxy) -1] -Piperidyl] -2-benzothiazolyloxy group, 2- [4- (3-fluorophenoxy) -1-piperidyl] -4-benzothiazolyloxy group, 2- [4- (4-fluorophenoxy) group -1-piperazinyl] -5-benzothiazolyloxy group, 2- [4- (2-chlorophenoxy) -1-piperidyl] -6-benzothiazolyloxy group, 2- [4- (3-chloro) group Phenoxy) -1- Peridyl] -7-benzothiazolyloxy group, 5- [4- (4-chlorophenoxy) -1-piperidyl] -4-benzothiazolyloxy group, 6- [4- (2,3-dichlorophenoxy) group ) -L-Piperidyl] -4-benzothiazolyloxy group, 7- [4- (2,4-dichlorophenoxy) -1-piperidyl] -4-benzothiazolyloxy group, 2- [4- ( 3,4-Dichlorophenoxy) -1-piperidyl] -4-benzothiazolyloxy group, 4- [4- (3,5-dichlorophenoxy) -1-piperidyl] -2-benzothiazolyloxy group, 4- [4- (3,4,5-trichlorophenoxy) -1-piperidyl] -5-benzothiazolyloxy group, 4- [4- (2,3,4,5,6-pentafluorophenoxy) -1-piperidyl] -2- Group [4- (4- (2-trifluoromethylphenoxy) -1-piperidyl] -6-benzothiazolyloxy group, 4- [4- (3-trifluoromethylphenoxy)-] 1-piperidyl] -7-benzothiazolyloxy group, 2- [4- (4-trifluoromethylphenoxy) -1-piperidyl] -4-benzothiazolyloxy group, 5- [4- (4- (4-) Methylphenoxy) -1-piperidyl] -4-benzothiazolyloxy group, 6- [4- (3,4-dimethylphenoxy) -1-piperidyl] -4-benzothiazolyloxy group, 7- [4 -(2,4,6-trimethylphenoxy) -1-piperidyl] -4-benzothiazolyloxy group, 4- [4- (2-pentafluoroethyl phenoxy) -1-piperidyl] -2-benzothiazo Ryloxy group, 4- [4- (3-pentafluoroethyl phenoxy) -1-piperidyl] -5-benzothiazolyloxy group, 4- [4- (4-pentafluoroethyl phenoxy) -1-piperidyl]- 6-benzothiazolyloxy group, 4- [4- (2-trifluoromethoxyphenoxy) -1-piperidyl] -7-benzothiazolyloxy group, 5- [4- (3-trifluoromethoxyphenoxy) group -1-piperidyl] -4-benzothiazolyloxy group, 6- [4- (4-trifluoromethoxyphenoxy) -1-piperidyl] -5-benzothiazolyloxy group, 7- [4- (4) -Methoxyphenoxy) -1-piperidyl] -5-benzothiazolyloxy group, 6- [4- (3,4-dimethoxyphenoxy) -1-piperidyl] -4-benzothia Ryloxy group, 7- [4- (2,4,6-trimethoxyphenoxy) -1-piperidyl] -4-benzothiazolyloxy group, 5- [4- (2-pentafluoroethoxyphenoxy) -1-] Piperidyl] -4-benzothiazolyloxy, 4- [4- (3-pentafluoroethoxyphenoxy) -1-piperidyl] -2-benzothiazolyloxy, 6- [4- (4-pentafluoro] Ethoxyphenoxy) -1-piperidyl] -4-benzothiazolyloxy group 2,5,6-triphenyl-7-benzothiazolyloxy group 2- (4-amino-1-piperidyl) -6- Benzothiazolyloxy group, 4- (2,4-diamino-1-piperidyl) -2-benzothiazolyloxy group, 5- (2,4,6-triamino-1-piperidyl) -4-benzo Azolyloxy group, 6- (2-amino-1-piperidyl) -5-benzothiazolyloxy group, 7- (3-amino-1-piperidyl) -6-benzothiazolyloxy group, 2- (4-) Methylamino-1-piperidyl) -4-benzothiazolyloxy group, 2- (4-ethylamino-1-piperidyl) -5-benzothiazolyloxy group, 2- (4-n-propylamino-1) -Piperidyl) -6-benzothiazolyloxy group, 2- (4-dimethylamino-1-piperidyl) -7-benzothiazolyloxy group, 2- (4-diethylamino-1-piperidyl) -4-benzo Thiazolyloxy group, 2- (4-di-n-propylamino-1-piperidyl) -5-benzothiazolyloxy group, 2- (4-phenylamino-1-piperidyl) -6-benzothiazolyl Oxy group, 2- [4- (N-phenyl-N-methylamino) -1-piperidyl] -7-benzothiazolyloxy group, 2- [4- (2-fluorophenylamino) -1-piperidyl] -4-benzothiazolyloxy group, 2- [4- (3-fluorophenylamino) -1-piperidyl] -5-benzothiazolyloxy group, 2- [4- (4-fluorophenylamino)- 1-piperidyl] -6-benzothiazolyloxy group, 2- [4- (2-chlorophenylamino) -1-piperidyl] -7-benzothiazolyloxy group, 2- [4- (3-chlorophenylamino] )-1-Piperidyl] -4-benzothiazolyloxy group, 2- [4- (4-chlorophenylamino) -1-piperidyl] -5-benzothiazolyloxy group, 2- [4- (2, 3-dichloro Phenylamino) -1-piperidyl] -6-benzothiazolyloxy group, 2- [4- (2,4,6-trifluorophenylamino) -1-piperidyl] -7-benzothiazolyloxy group, 2 -[4- (2,4-dichlorophenylamino) -1-piperidyl] -4-benzothiazolyloxy group, 2- [4- (3,4-dichlorophenylamino) -1-piperidyl] -6-benzothia Zoryloxy group, 4- (3,5-dichlorophenylamino) -1-piperidyl] -5-benzothiazolyloxy group, 2- [4- (2,3,4,5,6-pentafluorophenylamino] )-1-Piperidyl] -6-benzothiazolyloxy group, 2- [4- (2-trifluoromethylphenylamino) -1-piperidyl] -7-benzothiazolyloxy group, 2- [4- 2-Methylphenylamino) -1-piperidyl] -4-benzothiazolyloxy group, 2- [4- (2,3-dimethylphenylamino) -1-piperidyl] -5-benzothiazolyloxy group, 2- [4- (2-trifluoromethylphenylamino) -1-piperidyl] -6-benzothiazolyloxy group, 2- [4- (2,4,6-trimethylphenylamino) -1-piperidyl] -7-benzothiazolyloxy group, 2- [4- (4-trifluoromethylphenylamino) -1-piperidyl] -4-benzothiazolyloxy group, 2- [4- (2-pentafluoroethyl) group Phenylamino) -1-piperidyl] -5-benzothiazolyloxy group, 2- [4- (3-pentafluoroethylphenylamino) -1-piperidyl] -5-benzothiazolyloxy Xy group, 2- [4- (4-pentafluoroethylphenylamino) -1-piperidyl] -6-benzothiazolyloxy group, 2- [4- (2-trifluoromethoxyphenylamino) -1-piperidyl ] -7-benzothiazolyloxy group, 2- [4- (2-methoxyphenylamino) -1-piperidyl] -4-benzothiazolyloxy group, 2- [4- (2,3-dimethoxyphenyl) group Amino) -1-piperidyl] -5-benzothiazolyloxy group, 2- [4- (2,4,6-trimethoxyphenylamino) -1-piperidyl] -6-benzothiazolyloxy group, 2 -{4- [N-methyl-N- (2,4,6-trimethoxyphenylamino)]-1-piperidyl} -7-benzothiazolyloxy group, 2- {4- [N-methyl-N -(3,4-dimethy Phenylamino)]-1-piperidyl} -4-benzothiazolyloxy group, 2- [4- (3-trifluoromethoxyphenylamino) -1-piperidyl] -5-benzothiazolyloxy group, 2- [4- (4-Trifluoromethoxyphenylamino) -1-piperidyl] -6-benzothiazolyloxy group, 2- [4- (2-pentafluoroethoxyphenylamino) -1-piperidyl] -7-benzo Thiazolyloxy group, 2- [4- (3-pentafluoroethoxyphenylamino) -1-piperidyl] -4-benzothiazolyloxy group, 2- [4- (4-pentafluoroethoxyphenylamino)- 1-piperidyl] -5-benzothiazolyloxy group, 2- [4- (2-fluorophenylamino) -1-piperidyl] -5-benzothiazolyl Xy group, 4- (3-fluorophenylamino) -1-piperidyl] -6-benzothiazolyloxy group, 2- [4- (4-fluorophenylamino) -1-piperidyl] -7-benzothiazole Roxy group, 2-phenyl-5- (4-phenoxy-1-piperidyl) -7-benzothiazolyloxy group, 2- [1- (4-trifluoromethoxyphenyl)-(2- or 3-) Pyrrolyl]-(4-, 5-, 6- or 7-) benzothiazolyloxy group, 2- [1-methyl- (2- or 3-) pyrrolyl]-(4-, 5-, 6- or 7-) benzothiazolyloxy group, 2- {4- [3- (4-trifluoromethylphenyl) -2-propenyl]-(1-, 2- or 3-) piperazinyl}-(4-, 5 -, 6- or 7-) benzothiazolyloxy group, 2- [4 -(4-Trifluoromethoxyphenyl)]-(1-, 2- or 3-) piperazinyl- (4-, 5-, 6- or 7-) benzothiazolyloxy group, 2- [4- (4) -Trifluoromethylphenyl)]-(1-, 2- or 3-) piperazinyl- (4-, 5-, 6- or 7-


) Benzothiazolyloxy groups such as benzothiazolyloxy group, 2- (4-chlorophenylthio)-(4-, 5-, 6- or 7-) benzothiazolyloxy group (on a benzothiazole ring) (B-1) phenyl group [a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group, and a halogen substituted or unsubstituted C1-6 alkoxy group on a phenyl ring Or (b-2) a piperazinyl group [in the piperazine ring, a phenyl C.sub.1-6 alkyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1 group, -6 alkyl group and at least one group selected from the group consisting of halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted), the alkenyl moiety having 2 to 6 carbon atoms, and a double bond The Phenyl C2-6 alkenyl group (a halogen atom, halogen substituted or unsubstituted on the phenyl ring, containing 1 to 3 linear or branched alkenyl groups, including both trans and cis isomers) 1 to 5, preferably 1 to 3 groups selected from the group consisting of C1-6 alkyl groups and halogen-substituted or unsubstituted C1-6 alkoxy groups, and phenyl groups (phenyl There are 1 to 5 groups, preferably 1 to 3 groups selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group on the ring. And 1 to 3 groups selected from the group consisting of (optionally substituted) may be substituted], (b-3) piperidyl group [in the piperidine ring, an amino group (on the amino group , Phenyl group [phenyl ring And at least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted At least one of a group selected from the group consisting of a C1-6 alkyl group may be substituted, a phenoxy group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and And at least one of a group selected from the group consisting of halogen substituted or unsubstituted C1-6 alkoxy group may be substituted) and phenyl C1-6 alkyl group (on the phenyl ring, halogen atom, halogen substituted Or at least one group selected from the group consisting of unsubstituted C1-6 alkyl groups and halogen-substituted or unsubstituted C1-6 alkoxy groups At least one of the groups selected from the group consisting of (optionally substituted) may be substituted], (b-4) pyrrolyl group [C1-6 alkyl group on the pyrrole ring and phenyl A C1-6 alkyl group (on the phenyl ring, a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group is selected from 1 to 5) 1-3, preferably, 1 to 3 groups selected from the group consisting of 1 to 3 may be substituted] may be substituted 1 to 3) and (b-5) phenylthio group [on the phenyl ring 1-5, preferably 1-3, are selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group Selected from the group consisting of And the like groups may be substituted with 1 to 3 groups].

  [Piperazinyl group [on a piperazine ring, a phenyl C.sub.1-6 alkyl group (on a phenyl ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group is included. At least one of the groups selected from the group may be substituted), phenyl group [a phenoxy group on a phenyl ring (a halogen atom, a halogen substituted or unsubstituted C1 to 6 alkyl on a phenyl ring, Group and at least one group selected from the group consisting of halogen substituted or unsubstituted C1-6 alkoxy group may be substituted), halogen atom, halogen substituted or unsubstituted C1-6 alkyl group and halogen And at least one group selected from the group consisting of substituted or unsubstituted C1-6 alkoxy groups may be substituted] and [C2-6 alkenyl group [wherein at least one of the groups selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group on a phenyl ring As the piperazinyl group [in the piperazine ring, at least one phenyl C 1 -6 alkyl group may be substituted as at least one of the groups selected from the group consisting of a species may be substituted] Group (on the phenyl ring, at least one of a group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group is substituted) May be substituted], 4- [3- (4-trifluoromethylphenyl) -2-propenyl]-(1-, 2-) Is 3-) piperazinyl group, 4- (4-methoxyphenyl)-(1-, 2- or 3-) piperazinyl group, 4- (3,4-dimethylphenyl)-(1-, 2- or 3-) Piperazinyl group, 4- (4-fluorophenyl)-(1-, 2- or 3-) piperazinyl group, 4- (4-trifluoromethylphenyl)-(1-, 2- or 3-) piperazinyl group, 4 -(4-Methylphenyl)-(1-, 2- or 3-) piperazinyl group, 4- (3,4-dichlorophenyl)-(1-, 2- or 3-) piperazinyl group, 4- (4-triphenyl) group Piperazinyl groups such as fluoromethoxyphenyl)-(1-, 2- or 3-) piperazinyl group, 4- [4- (4-chlorophenoxy) phenyl]-(1-, 2- or 3-) piperazinyl group [piperazine On the ring, phenyl C 1 to 6 Alkyl group (on the phenyl ring, 1 to 5 groups selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group are preferred, Is optionally substituted 1 to 3), phenyl group [on the phenyl ring, a phenoxy group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or not substituted. 1 to 5, preferably 1 to 3 groups selected from the group consisting of substituted C1-6 alkoxy groups may be substituted, halogen atoms, halogen substituted or unsubstituted C1-6 alkyl groups, and 1-5, preferably 1 to 3 groups selected from the group consisting of halogen-substituted or unsubstituted C1-6 alkoxy groups may be substituted] and alkenyl groups A linear or branched alkenyl group having a prime number of 2 to 6 and 1 to 3 double bonds, including both trans and cis forms; phenyl C 2-6 alkenyl group [on phenyl ring Is substituted by 1 to 5, preferably 1 to 3 groups selected from the group consisting of halogen atoms, halogen-substituted or unsubstituted C.sub.1-6 alkyl groups and halogen-substituted or unsubstituted C.sub.1-6 alkoxy groups; And the group selected from the group which may be substituted] may be substituted 1-3.

  As the naphthyl C1-6 alkyl group, for example, [(1- or 2-) naphthyl] methyl group, 1-[(1- or 2-) naphthyl] ethyl group, 2-[(1- or 2-) naphthyl group Ethyl group, 3-[(1- or 2-) naphthyl] propyl group, 2-[(1- or 2-) naphthyl] propyl group, 4-[(1- or 2-) naphthyl] butyl group, 5 -[(1- or 2-) naphthyl] pentyl group, 4-[(1- or 2-) naphthyl] pentyl group, 6-[(1- or 2-) naphthyl] hexyl group, 2-methyl-3- C1-C6 linear or branched alkyl moiety of alkyl moiety such as [(1- or 2-) naphthyl] propyl group, 1,1-dimethyl-2-[(1- or 2-) naphthyl] ethyl group It is possible to exemplify a naphthylalkyl group which is a cyclic alkyl group.

  Phenyl C1-6 alkylidene group (in which at least one of the groups selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group on the phenyl ring The species may be substituted), for example, benzylidene group, 1-phenylethylidene group, 2-phenylethylidene group, 3-phenylpropylidene group, 2-phenylpropylidene group, 4-phenylbutylidene group, 5-phenylpropylidene group Phenyl pentylidene group, 4-phenyl pentylidene group, 6-phenylhexylidene group, 2-fluorobenzylidene group, 3-fluorobenzylidene group, 4-fluorobenzylidene group, 2-chlorobenzylidene group, 3-chlorobenzylidene group, 4-chlorobenzylidene group, 2-bromobenzylidene group, 3 Bromobenzylidene group, 4-bromobenzylidene group, 2-iodobenzylidene group, 3-iodobenzylidene group, 4-iodobenzylidene group, 2,3-difluorobenzylidene group, 3,4-difluorobenzylidene group, 3,5-difluorobenzylidene Group, 2,4-difluorobenzylidene group, 2,6-difluorobenzylidene group, 2,3-dichlorobenzylidene group, 3,4-dichlorobenzylidene group, 3,5-dichlorobenzylidene group, 2,4-dichlorobenzylidene group, 2,6-dichlorobenzylidene group, 2-fluoro-4-bromobenzylidene group, 4-chloro-3-fluorobenzylidene group, 2,3,4-trichlorobenzylidene group, 3,4,5-trifluorobenzylidene group, 2 , 4, 6- trichlorobenzylidene group, 4- isopropyl Benzylidene group, 4-n-butylbenzylidene group, 4-methylbenzylidene group, 2-methylbenzylidene group, 3-methylbenzylidene group, 2,4-dimethylbenzylidene group, 2,3-dimethylbenzylidene group, 2, 6- Dimethylbenzylidene group, 3,5-dimethylbenzylidene group, 2,5-dimethylbenzylidene group, 2,4,6-trimethylbenzylidene group, 3,5-ditrifluoromethylbenzylidene group, 2,3,4,5,6- Pentafluorobenzylidene group, 4-isopropoxybenzylidene group, 4-n-butoxybenzylidene group, 4-methoxybenzylidene group, 2-methoxybenzylidene group, 3-methoxybenzylidene group, 2,4-dimethoxybenzylidene group, 2,3- Dimethoxybenzylidene, 2,6-Dimethoxybenzylidene Group, 3,5-dimethoxybenzylidene group, 2,5-dimethoxybenzylidene group, 2,4,6-trimethoxybenzylidene group, 3,5-ditrifluoromethoxybenzylidene group, 2-isopropoxybenzylidene group, 3-chloro- 4-methoxybenzylidene group, 2-chloro-4-trifluoromethoxybenzylidene group, 3-methyl-4-fluorobenzylidene group, 4-bromo-3-trifluoromethylbenzylidene group, 2-trifluoromethylbenzylidene group, 3- Trifluoromethylbenzylidene group, 4-trifluoromethylbenzylidene group, 2-pentafluoroethyl benzylidene group, 3-pentafluoroethyl benzylidene group, 4-pentafluoroethyl benzylidene group, 2-trifluoromethoxybenzylidene group, 3-trifluoromethane Xyzylidene group, 4-trifluoromethoxybenzylidene group, 2-pentafluoroethoxybenzylidene group, 3-pentafluoroethoxybenzylidene group, 4-pentafluoroethoxybenzylidene group, 2- (2-trifluoromethylphenyl) ethylidene group, 2 -(3-Trifluoromethylphenyl) ethylidene group, 2- (4-trifluoromethylphenyl) ethylidene group, 2- (2-trifluoromethoxyphenyl) ethylidene group, 2- (3-trifluoromethoxyphenyl) ethylidene group , 2- (4-trifluoromethoxyphenyl) ethylidene group, 2- (2-pentafluoroethoxyphenyl) ethylidene group, 2- (3-pentafluoroethoxyphenyl) ethylidene group, 2- (4-pentafluoroethoxyphenyl) group Echiri Group, 3- (2-trifluoromethylphenyl) propylidene group, 3- (3-trifluoromethylphenyl) propylidene group, 3- (4-trifluoromethylphenyl) propylidene group, 3- (2-trifluoromethoxy) group Phenyl) propylidene group, 3- (3-trifluoromethoxyphenyl) propylidene group, 3- (4-trifluoromethoxyphenyl) propylidene group, 3- (3-pentafluoroethoxyphenyl) propylidene group, 3- (4-pentafluoroethylphenyl) propylidene group Fluoroethoxyphenyl) propylidene group, 4- (3-pentafluoroethoxyphenyl) butylidene group, 5- (4-trifluoromethylphenyl) pentylidene group, 4- (4-trifluoromethylphenyl) pentylidene group, 4- (4 -Trifluoromethoxyphenyl) pentyl Phenyl C1-6 alkylidene groups such as den group, 6- (3-trifluoromethylphenyl) hexylidene group, 6- (4-trifluoromethylphenyl) hexylidene group, 6- (4-trifluoromethoxyphenyl) hexylidene group, etc. On the phenyl ring, 1 to 5 groups, preferably 1 to 6 groups selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group are preferable. 3) may be mentioned.

  Piperazinyl group [C1-6 alkoxycarbonyl group on piperazine ring, furyl C1-6 alkyl group [at least one phenyl group on furan ring (halogen atom on halogen ring, halogen-substituted or unsubstituted In which at least one of a group selected from the group consisting of a C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted), 6 alkyl groups [containing a furyl group and a phenyl group on a pyridine ring (on a phenyl ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group. At least one group selected from the group consisting of at least one group selected from the group may be substituted), Zothienyl C1-6 alkyl group (on the benzothiophene ring, at least one of a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group 1 type may be substituted, phenyl C2-6 alkenyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group At least one of a group selected from the group consisting of: a benzofuryl C1-6 alkyl group [a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen on the benzofuran ring At least one of a group selected from the group consisting of a substituted or unsubstituted C1-6 alkoxy group may be substituted], Zofuryl C2-6 alkenyl group [in the benzofuran ring, at least one of the groups selected from the group consisting of halogen atoms, halogen substituted or unsubstituted C1-6 alkyl groups and halogen substituted or unsubstituted C1-6 alkoxy groups Species may be substituted], thiazolyl C1-6 alkyl group [in at least one phenyl group on the thiazole ring (a halogen atom, halogen substituted or unsubstituted C1-6 alkyl group on the phenyl ring) And at least one group selected from the group consisting of halogen-substituted or unsubstituted C1-6 alkoxy groups may be substituted), phenoxy C1-6 alkyl group (phenyl ring Above, it consists of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group At least one group selected from the group may be substituted, indolyl C1-6 alkyl group (on the indole ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or And at least one group selected from the group consisting of unsubstituted C1-6 alkoxy groups may be substituted) and phenyl C1-6 alkyl groups (on the phenyl ring, benzofuryl group, halogen atoms, halogen substituted Or at least one group selected from the group consisting of an unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group at least one group selected from the group consisting of As the 1 type may be substituted, for example, as the piperazinyl group [on the piperazine ring, at least one phenyl C.sub.1-6 alkyl group Even if at least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group is substituted on the nyl ring In addition to 4- (4-[(2-, 3-, 4-, 4-, 4-)-butoxycarbonyl- (1-, 2- or 3-) piperazinyl group]. 5-, 6- or 7-) benzofuryl] benzyl}-(1-, 2- or 3-) piperazinyl group, 4- {3-[(2- or 3-) furyl] pyridylmethyl}-(1-, 2- or 3-) piperazinyl group, 4- [2- (4-trifluoromethoxyphenyl) pyridylmethyl]-(1-, 2- or 3-) piperazinyl group, 4- [2- (3-chloro-4) -Fluorocyphenyl) pyridylmethyl]-(1 , 2- or 3-) piperazinyl group, 4- [5-trifluoromethyl- (2-, 3-, 4-, 6- or 7-) benzofurylmethyl]-(1-, 2- or 3-) Piperazinyl group, 4- [6-trifluoromethyl- (2-, 3-, 4-, 5- or 7-) benzofurylmethyl]-(1-, 2- or 3-) piperazinyl group, 4- [5 -Chloro- (2-, 3-, 4-, 6- or 7-) benzothienylmethyl]-(1-, 2- or 3-) piperazinyl group, 4- [6-chloro- (2-, 3-) , 4-, 5- or 7-) benzofurylmethyl]-(1-, 2- or 3-) piperazinyl group, 4- [5-trifluoromethoxy- (2-, 3-, 4-, 6- or 7-) Benzofurylmethyl]-(1-, 2- or 3-) piperazinyl group, 4- [3- (4-trifluoromethyl) Phenyl) -2-propenyl]-(1-, 2- or 3-) piperazinyl group, 4- [3- (3,4-dichlorophenyl) -2-propenyl]-(1-, 2- or 3-) piperazinyl Group, 4- [3- (4-chlorophenyl) -2-propenyl]-(1-, 2- or 3-) piperazinyl group, 4- {3- [6-trifluoromethyl- (2-, 3-, 6 4-, 5- or 7-) benzofuryl] -2-propenyl}-(1-, 2- or 3-) piperazinyl group, 4- {3- [5-chloro- (2-, 3-, 4-, 4-, 5-, 4-) 5- or 7-) benzofuryl] -2-propenyl}-(1-, 2- or 3-) piperazinyl group, 4- [5-chloro- (2-, 3-, 4-, 6- or 7-) Benzofurylmethyl]-(1-, 2- or 3-) piperazinyl group, 4- [2- (4-trifluoro] Ethylphenyl)-(4- or 5-) thiazolylmethyl]-(1-, 2- or 3-) piperazinyl group, 4- [2- (4-trifluoromethoxyphenoxy) ethyl]-(1-, 2- or 3 -) Piperazinyl group, 4- [3- (4-trifluoromethoxyphenyl) -2-propenyl]-(1-, 2- or 3-) piperazinyl group, 4- [5-trifluoromethoxy- (1-, 2-, 3-, 4-, 6- or 7-) indolylmethyl]-(1-, 2- or 3-) piperazinyl group, 4- [2- (4-chlorophenyl)-(3-, 4-) Or 5-) furylmethyl]-(1-, 2- or 3-) piperazinyl group, 4- [2- (2-chloro-5-trifluoromethylphenyl)-(3-, 4- or 5-) furyl Methyl]-(1-, 2- or 3-) piperazinyl group etc. On the piperazine ring, a C1-6 alkoxycarbonyl group, a furyl C1-6 alkyl group in which the alkyl moiety is a linear or branched alkyl group having 1 to 6 carbon atoms [1 to 3 on the furan ring (1 to 5 groups selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group, and a halogen-substituted or unsubstituted C1-6 alkoxy group on the phenyl ring, Preferably, 1 to 3 of which may be substituted) may be substituted], a pyridyl C1-6 alkyl group [pyridine having an alkyl moiety of a linear or branched alkyl group having 1 to 6 carbon atoms] On the ring, a furyl group and a phenyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group are selected. Group may be substituted by 1 to 3 groups selected from the group consisting of 1 to 5 groups, preferably 1 to 3 groups), and the alkyl moiety has 1 to 5 carbon atoms Benzothienyl C.sub.1-6 alkyl group which is a linear or branched alkyl group of 6 (a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1 on the benzothiophene ring) Group selected from the group consisting of -6 alkoxy group may be substituted by 1 to 3), a straight or branched chain having 2 to 6 carbon atoms and 1 to 3 double bonds in the alkenyl moiety Phenyl C2-6 alkenyl group (including a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or non-halogenated group on the phenyl ring), including both a trans isomer and a cis isomer Substitution of C1 to C6 1 to 5, preferably 1 to 3 groups selected from the group consisting of alkoxy groups may be substituted), and the alkyl moiety is a linear or branched alkyl group having 1 to 6 carbon atoms Benzofuryl C1-6 alkyl group [in the benzofuran ring, a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group is selected And the alkenyl moiety is a linear or branched alkenyl group having 2 to 6 carbon atoms and 1 to 3 double bonds, and it may be a trans or cis isomer. Benzofuryl C 2-6 alkenyl group [in the benzofuran ring, a group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group Selected groups may be substituted by 1 to 3 groups], thiazolyl C.sub.1-6 alkyl groups wherein the alkyl moiety is a linear or branched alkyl group having 1 to 6 carbon atoms [on the thiazole ring And one or two phenyl groups (on the phenyl ring, a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group. 1-5, preferably 1-3, may be substituted), phenoxy C1 wherein the alkyl moiety is a linear or branched alkyl group having 1 to 6 carbon atoms 6 alkyl groups (1 to 5 groups selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group on the phenyl ring, Preferably 1 to 3 substitution An indolyl C1-6 alkyl group in which the alkyl moiety is a linear or branched alkyl group having 1 to 6 carbon atoms (on the indole ring, a halogen atom, a halogen substituted or unsubstituted C1 And a group selected from the group consisting of an alkyl group of 6 to 6 and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted with 1 to 3) and a phenyl C1-6 alkyl group (on the phenyl ring) 1 to 5, preferably 1 to 3 groups selected from the group consisting of a benzofuryl group, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group And one to three groups selected from the group consisting of (1) may be substituted.

The piperidyl group [a piperidine ring is an amino group (an amino group is a phenyl group [a phenyl group is a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1 At least one group selected from the group consisting of 6 alkoxy groups may be substituted] and at least one group selected from the group consisting of a C1-6 alkyl group may be substituted); A phenoxy group (in which at least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group is substituted on a phenyl ring; Phenyl C1-6 alkyl group (on the phenyl ring, a C1 to 4 alkylenedioxy group, a halogen atom, halogen substituted or unsubstituted At least one of a group selected from the group consisting of a C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group may be substituted; a phenyl C1-6 alkoxy group (on the phenyl ring) And at least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted; phenyl group (On the phenyl ring, at least one of a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group is substituted Naphthyl C1-6 alkyl group and phenyl C1-6 alkylidene group (on the phenyl ring, halogen atoms, halogen A group selected from the group consisting of a substituted or unsubstituted C1-6 alkyl group and a group selected from the group consisting of a halogen-substituted or unsubstituted C1-6 alkoxy group; As at least one member of the above may be substituted], for example, 1-piperidyl group, 2-piperidyl group, 3-piperidyl group, 4-piperidyl group, 2,4-diamino-1-piperidyl group, 2, 4,6-Triamino-1-piperidyl group, 2-amino-1-piperidyl group, 3-amino-1-piperidyl group, 4-amino-1-piperidyl group, 4-methylamino-1-piperidyl group, 4- Ethylamino-1-piperidyl group, 4-n-propylamino-1-piperidyl group, 4-dimethylamino-1-piperidyl group, 4-diethylamino-1-piperidyl group, 4- Di-n-propylamino-1-piperidyl group, 4-phenylamino-1-piperidyl group, 4- (N-phenyl-N-methylamino) -1-piperidyl group, 4- (2-fluorophenylamino)- 1-piperidyl group, 4- (3-fluorophenylamino) -1-piperidyl group, 4- (4-fluorophenylamino) -1-piperidyl group, 4- (2-chlorophenylamino) -1-piperidyl group, 4 -(3-chlorophenylamino) -1-piperidyl group, 4- (4-chlorophenylamino) -1-piperidyl group, 4- (2,3-dichlorophenylamino) -1-piperidyl group, 4- (2,4,4 6-trifluorophenylamino) -1-piperidyl group, 4- (2,4-dichlorophenylamino) -1-piperidyl group, 4- (3,4-dichlorophenyl) Amino) -1-piperidyl group, 4- (3,5-dichlorophenylamino) -1-piperidyl group, 4- (2,3,4,5,6-pentafluorophenylamino) -1-piperidyl group, 4- (2-trifluoromethylphenylamino) -1-piperidyl group, 4- (2-methylphenylamino) -1-piperidyl group, 4- (2,3-dimethylphenylamino) -1-piperidyl group, 4- (4- 3-trifluoromethylphenylamino) -1-piperidyl group, 4- (2,4,6-trimethylphenylamino) -1-piperidyl group, 4- (4-trifluoromethylphenylamino) -1-piperidyl group, 4- (2-pentafluoroethylphenylamino) -1-piperidyl group, 4- (3-pentafluoroethylphenylamino) -1-piperidyl group, 4- 4-pentafluoroethylphenylamino) -1-piperidyl group, 4- (2-trifluoromethoxyphenylamino) -1-piperidyl group, 4- (2-methoxyphenylamino) -1-piperidyl group, 4- (2) , 3-Dimethoxyphenylamino) -1-piperidyl group, 4- (2,4,6-trimethoxyphenylamino) -1-piperidyl group, 4- [N-methyl-N- (2,4,6-triyl group Methoxyphenylamino)]-1-piperidyl group, 4- [N-methyl-N- (3,4-dimethylphenylamino)]-1-piperidyl group, 4- [N-ethyl-N- (4-chlorophenylamino) )]-Piperidyl group, 4- (3-trifluoromethoxyphenylamino) -1-piperidyl group, 4- (4-trifluoromethoxyphenylamino) -1-piperi Zyl group, 4- (2-pentafluoroethoxyphenylamino) -1-piperidyl group, 4- (3-pentafluoroethoxyphenylamino) -1-piperidyl group, 4- (4-pentafluoroethoxyphenylamino) -1 -Piperidyl group, 4- [N-methyl-N- (2-fluorophenyl) amino] -1-piperidyl group, 4- [N-methyl-N- (3-fluorophenyl) amino] -1-piperidyl group, 4- [N-methyl-N- (4-fluorophenyl) amino] -1-piperidyl group, 4-phenoxy-1-piperidyl group, 2,4-diphenoxy-1-piperidyl group, 2,4,6-triyl group Phenoxy-1-piperidyl group, 2- (2-fluorophenoxy) -1-piperidyl group, 3- (3-fluorophenoxy) -2-piperidyl group, 4- (4-fluorophenyl) Orophenoxy) -3-piperidyl group, 2- (2-chlorophenoxy) -4-piperidyl group, 3- (3-chlorophenoxy) -5-piperidyl group, 4- (4-chlorophenoxy) -1-piperidyl group , 5- (2-bromophenoxy) -2-piperidyl group, 6- (3-bromophenoxy) -3-piperidyl group, 4- (4-bromophenoxy) -1-piperidyl group, 3- (2,3-) Dichlorophenoxy) -2-piperidyl group, 4- (3,4-dichlorophenoxy) -3-piperidyl group, 3- (2,4-dichlorophenoxy) -4-piperidyl group, 2- (3,4,5-) Trichlorophenoxy) -3-piperidyl group, 6- (2,4,6-trichlorophenoxy) -2-piperidyl group, 3- (2,3,4,5,6-pentafluorophenoxy) -1- Peridyl group, 4- (2-methylphenoxy) -1-piperidyl group, 5- (3-methylphenoxy) -2-piperidyl group, 6- (4-methylphenoxy) -3-piperidyl group, 4- (2- Ethylphenoxy) -1-piperidyl group, 2- (3-ethylphenoxy) -1-piperidyl group, 3- (4-ethylphenoxy) -2-piperidyl group, 4- (4-n-propylphenoxy) -3- Piperidyl group, 3- (4-tert-butylphenoxy) -4-piperidyl group, 2- (4-n-butylphenoxy) -3-piperidyl group, 1- (2-trifluoromethylphenoxy) -2-piperidyl group , 2- (3-trifluoromethylphenoxy) -1-piperidyl group, 4- (4-trifluoromethylphenoxy) -1-piperidyl group, 1- (2-pentafluo) Roethylphenoxy) -4-piperidyl group, 4- (3-pentafluoroethylphenoxy) -1-piperidyl group, 4- (2,3-dimethylphenoxy) -1-piperidyl group, 4- (3,4,5 -Trimethylphenoxy) -1-piperidyl group, 4- (4-n-pentylphenoxy) -1-piperidyl group, 4- (4-n-hexylphenoxy) -1-piperidyl group, 4- (2-methoxyphenoxy) group -1-piperidyl group, 4- (3-methoxyphenoxy) -1-piperidyl group, 4- (4-methoxyphenoxy) -1-piperidyl group, 2- (2-ethoxyphenoxy) -3-piperidyl group, 3- (3-Ethoxyphenoxy) -4-piperidyl group, 4- (4-ethoxyphenoxy) -3-piperidyl group, 3- (4-n-propoxyphenoxy) -2- Peridyl group, 2- (4-tert-butoxyphenoxy) -1-piperidyl group, 4- (4-n-butoxyphenoxy) -2-piperidyl group, 2- (2-trifluoromethoxyphenoxy) -3-piperidyl group 3- (3-trifluoromethoxyphenoxy) -4-piperidyl group, 4- (4-trifluoromethoxyphenoxy) -3-piperidyl group, 3- (2-pentafluoroethoxyphenoxy) -2-piperidyl group, 2 -(4-pentafluoroethoxyphenoxy) -1-piperidyl group, 4- (2,3-dimethoxyphenoxy) -14-piperidyl group, 4- (3,4,5-trimethoxyphenoxy) -1-piperidyl group, 4- (4-n-Pentyloxyphenoxy) -1-piperidyl group, 4- (4-n-hexyloxyphenoxy) -1 Piperidyl group, 4-benzyl-1-piperidyl group, 2,4-dibenzyl-1-piperidyl group, 2,4,6-tribenzyl-1-piperidyl group, 2- (2-fluorobenzyl) -1-piperidyl group, 3- [2- (3-fluorophenyl) ethyl] -2-piperidyl group, 4- [1- (4-fluorophenyl) ethyl] -3-piperidyl group, 2- [3- (2-chlorophenyl) propyl] -4-piperidyl group, 3- [4- (3-chlorophenyl) butyl] -5-piperidyl group, 4- [5- (4-chlorophenyl) pentyl] -2-piperidyl group, 5- [6- (2- (2-chlorophenyl) butyl] Bromophenyl) hexyl] -2-piperidyl group, 6- (3-bromobenzyl) -3-piperidyl group, 4- (4-bromobenzyl) -1-piperidyl group, 3- (2,3-dichlorobenzyl) And 4- (3,4-dichlorobenzyl) -3-piperidyl group, 3- (2,4-dichlorobenzyl) -4-piperidyl group, 2- (3,4,5-trichloro) Benzyl) -3-piperidyl group, 6- (2,4,6-trichlorobenzyl) -2-piperidyl group, 3- (2,3,4,5,6-pentafluorobenzyl) -1-piperidyl group, 4 -(2-methylbenzyl) -1-piperidyl group, 5- [2- (3-methylphenyl) ethyl] -2-piperidyl group, 6- [3- (4-methylphenyl) propyl] -3-piperidyl group 1- [4- (2-ethylphenyl) butyl] -4-piperidyl group, 2- [5- (3-ethylphenyl) pentyl] -1-piperidyl group, 3- [6- (4-ethylphenyl) group Hexyl] -2-piperidyl group, -(4-n-propylbenzyl) -3-piperidyl group, 3- (4-tert-butylbenzyl) -4-piperidyl group, 2- (4-n-butylbenzyl) -3-piperidyl group, 1- (4-n-propylbenzyl) -3-piperidyl group 2-trifluoromethylbenzyl) -2-piperidyl group, 2- (3-trifluoromethylbenzyl) -1-piperidyl group, 4- (4-trifluoromethylbenzyl) -1-piperidyl group, 1- (2-) Pentafluoroethylbenzyl) -4-piperidyl group, 1- (3-pentafluoroethylbenzyl) -4-piperidyl group, 4- (2,3-dimethylbenzyl) -1-piperidyl group, 1- (3,4,3 5-trimethylbenzyl) -4-piperidyl group, 1- (4-n-pentylbenzyl) -4-piperidyl group, 4- (4-n-hexylbenzyl) -1-piperidyl group, -(2-methoxybenzyl) -1-piperidyl group, 1- [2- (3-methoxyphenyl) ethyl] -4-piperidyl group, 1- [1- (4-methoxyphenyl) ethyl] -4-piperidyl group 2- [3- (2-Ethoxyphenyl) propyl] -3-piperidyl group, 3- [4- (3-ethoxyphenyl) butyl] -4-piperidyl group, 4- [5- (4-ethoxyphenyl) group Pentyl] -3-piperidyl group, 3- [6- (4-n-propoxyphenyl) hexyl] -2-piperidyl group, 2- (4-tert-butoxybenzyl) -1-piperidyl group, 1- (4- (4-tert-butoxybenzyl) -1-piperidyl group) n-butoxybenzyl) -2-piperidyl group, 2- (2-trifluoromethoxybenzyl) -3-piperidyl group, 3- (3-trifluoromethoxybenzyl) -4-piperidyl group, 4- ( 4-trifluoromethoxybenzyl) -1-piperidyl group, 3- (2-pentafluoroethoxybenzyl) -2-piperidyl group, 2- (4-pentafluoroethoxybenzyl) -1-piperidyl group, 1- (2,2, 3-dimethoxybenzyl) -4-piperidyl group, 4- (3)


4,5-trimethoxybenzyl) -1-piperidyl group, 4- (4-n-pentyloxybenzyl) -1-piperidyl group, 4- (4-n-hexyloxybenzyl) -1-piperidyl group, 4 -Benzyl-3-phenoxy-1-piperidyl group, 4-phenoxy-2-methylamino-1-piperidyl group, 4- (4-trifluoromethoxybenzylidene) -1-piperidyl group, 4- (4-chlorobenzylidene) -1-piperidyl group, 4- (4-trifluoromethylbenzylidene) -1-piperidyl group, 4- (3,4-dichlorobenzyloxy)-(1-, 2- or 3-) piperidyl group, 4- (4-) 4-methylbenzyloxy)-(1-, 2- or 3-) piperidyl group, 4- (4-trifluoromethoxybenzyloxy)-(1-, 2- or 3-) piperi 4- (4-methoxyphenyl)-(1-, 2- or 3-) piperidyl group, 4- (3,4-dichlorophenyl)-(1-, 2- or 3-) piperidyl group, 4- [(1- or 2-) naphthylmethyl]-(1-, 2- or 3-) piperidyl group, 4- (3,4-methylenedioxyphenyl)-(1-, 2- or 3-) piperidyl group A piperidyl group such as 4- (4-chlorobenzyloxy)-(1-, 2- or 3-) piperidyl group [an amino group (on the piperidine ring; a phenyl group on the amino group; Is substituted by 1 to 5, preferably 1 to 3 groups selected from the group consisting of halogen atoms, halogen-substituted or unsubstituted C.sub.1-6 alkyl groups and halogen-substituted or unsubstituted C.sub.1-6 alkoxy groups; And C1-6 alkyl group A group selected from the group may be substituted by 1 to 2 groups; phenoxy group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1 1 to 5, preferably 1 to 3, groups selected from the group consisting of -6 alkoxy groups may be substituted; phenyl C1-6 alkyl group (on the phenyl ring, having 1 to 4 carbon atoms Or a group selected from the group consisting of a linear or branched C1-4 alkylenedioxy group, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group Is optionally substituted by 1 to 5, preferably 1 to 3; phenyl C1-6 alkoxy group (on the phenyl ring, a halogen atom, halogen substituted or unsubstituted C1-6 alkyl group; 1 to 5 and preferably 1 to 3 groups selected from the group consisting of halogen and halogen substituted or unsubstituted C.sub.1-6 alkoxy); phenyl group described above (phenyl ring Above, 1 to 5 groups, preferably 1 to 3 groups selected from the group consisting of halogen atoms, halogen substituted or unsubstituted C1-6 alkyl groups and halogen substituted or unsubstituted C1-6 alkoxy groups And may be substituted); naphthyl C1-6 alkyl group wherein the alkyl moiety is a linear or branched alkyl group having 1 to 6 carbon atoms and phenyl C1-6 alkylidene group (a halogen atom on the phenyl ring 1 to 5, preferably 1 to 3 groups selected from the group consisting of halogen-substituted or unsubstituted C1-6 alkyl groups and halogen-substituted or unsubstituted C1-6 alkoxy groups Conversion and selected from the group consisting of even may) have groups can be exemplified] may be in 1-3 substituents.

Quinolyloxy group (in the quinoline ring, (c-1) a halogen atom; (c-2) a phenoxy group [in the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or not substituted At least one group selected from the group consisting of substituted C1-6 alkoxy groups may be substituted], (c-3) piperazinyl group [in the piperazine ring, a phenyl C1-6 alkyl group (phenyl At least one selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted on the ring A phenyl group (on the phenyl ring, a phenoxy group [on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or not. At least one group selected from the group consisting of substituted C1-6 alkoxy groups may be substituted], a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1 And at least one group selected from the group consisting of -6 alkoxy groups and a phenyl C2-6 alkenyl group [on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6, At least one group selected from the group consisting of an alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted], at least one group selected from the group consisting of And (c-4) piperidyl group [an amino group (on the piperidine ring; a phenyl group on the amino group; a halogen atom on the phenyl ring, a halogen atom; At least one of a group selected from the group consisting of a substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted] and a C1-6 alkyl group At least one of the groups selected from the group may be substituted; phenoxy group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1; 66 alkoxy group optionally substituted by at least one group selected from the group consisting of ア ル コ キ シ 6 alkoxy group; phenyl C1-6 alkyl group (C1 to 4 alkylenedioxy group on halogen ring, halogen atom, halogen At least one group selected from the group consisting of a substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group A phenyl C1-6 alkoxy group (on the phenyl ring, a group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group, and a halogen substituted or unsubstituted C1-6 alkoxy group; At least one of the selected groups may be substituted); a phenyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1 At least one group selected from the group consisting of 6 alkoxy groups may be substituted); a naphthyl C1-6 alkyl group and a phenyl C1-6 alkylidene group (on the phenyl ring, a halogen atom, a halogen substitution or It is selected from the group consisting of an unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group At least one kind of groups may be substituted) and at least one kind of groups selected from the group consisting of And 2-quinolyloxy, 3-quinolyloxy, 4-quinolyloxy, 5-quinolyloxy, 6-quinolyloxy, 7-quinolyloxy, 8-quinolyloxy, 4- (1-piperazinyl). -2-quinolyloxy group, 3- (2-piperazinyl) -4-quinolyloxy group, 4- (1-piperazinyl) -3-quinolyloxy group, 5- (1-piperazinyl) -4-quinolyloxy group, 6- (3, 4-dibenzyl-1-piperazinyl) -5-quinolyloxy group, 7- (2,3,4-tribenzyl-1-piperazinyl) -6-quinolyloxy Group, 4- (4-benzyl-1-piperazinyl) -2-quinolyloxy group, 3- [4- (2-phenethyl) -1-piperazinyl] -2-quinolyloxy group, 4- [4- (3-phenylpropyl) group ) -1-Piperazinyl] -3-quinolyloxy group, 5- [4- (4-phenylbutyl) -1-piperazinyl] -4-quinolyloxy group, 6- [4- (5-phenylpentyl) -1-piperazinyl] -5-quinolyloxy group, 7- [4- (6-phenylhexyl) -1-piperazinyl] -6-quinolyloxy group, 8- [4- (2-fluorobenzyl) -1-piperazinyl] -7-quinolyloxy group, 2- [4- (3-fluorobenzyl) -1-piperazinyl] -8-quinolyloxy group, 3- [4- (4-fluorobenzyl) -1-piperazinyl] -2-ki Ryloxy group, 4- [4- (2-chlorobenzyl) -1-piperazinyl] -3-quinolyloxy group, 5- [4- (3-chlorobenzyl) -1-piperazinyl] -4-quinolyloxy group, 2- [4 4- (4-chlorobenzyl) -1-piperazinyl] -6-quinolyloxy group, 7- [4- (2,3-dichlorobenzyl) -1-piperazinyl] -6-quinolyloxy group, 8- [4- (2) , 4-Dichlorobenzyl) -1-piperazinyl] -7-quinolyloxy group, 2- [4- (3,4-dichlorobenzyl) -1-piperazinyl] -8-quinolyloxy group, 3- [4- (3,5) -Dichlorobenzyl) -1-piperazinyl] -2-quinolyloxy group, 4- [4- (3,4,5-trichlorobenzyl) -1-piperazinyl] -3-quinolyloxy group, 5- [ -(2,3,4,5,6-pentafluorobenzyl) -1-piperazinyl] -4-quinolyloxy group, 6- [4- (2-trifluoromethylbenzyl) -1-piperazinyl] -5-quinolyloxy group 7- [4- (3-trifluoromethylbenzyl) -1-piperazinyl] -6-quinolyloxy group, 2- [4- (4-trifluoromethylbenzyl) -1-piperazinyl] -6-quinolyloxy group, 2 -[4- (4-methylbenzyl) -1-piperazinyl] -8-quinolyloxy group, 3- [4- (3,4-dimethylbenzyl) -1-piperazinyl] -2-quinolyloxy group, 4- [4- (2,4,6-trimethylbenzyl) -1-piperazinyl] -3-quinolyloxy group, 5- [4- (2-pentafluoroethylbenzyl) -1-piperazinyl ] 4-quinolyloxy group, 6- [4- (3-pentafluoroethylbenzyl) -1-piperazinyl] -5-quinolyloxy group, 7- [4- (4-pentafluoroethylbenzyl) -1-piperazinyl]- 6-quinolyloxy group, 2- [4- (4-trifluoromethoxybenzyl) -1-piperazinyl] -6-quinolyloxy group, 2- [4- (3-trifluoromethoxybenzyl) -1-piperazinyl] -8- Quinolyloxy group, 3- [4- (4-trifluoromethoxybenzyl) -1-piperazinyl] -2-quinolyloxy group, 4- [4- (4-methoxybenzyl) -1-piperazinyl] -3-quinolyloxy group, 5 -[4- (3,4-Dimethoxybenzyl) -1-piperazinyl] -4-quinolyloxy group, 6- [4- (2,4,6-toly] Toxibenzyl) -1-piperazinyl] -5-quinolyloxy group, 7- [4- (2-pentafluoroethoxybenzyl) -1-piperazinyl] -6-quinolyloxy group, 8- [4- (3-pentafluoroethoxy benzyl] ) -1-Piperazinyl] -2-quinolyloxy group, 3- [4- (4-pentafluoroethoxybenzyl) -1-piperazinyl] -2-quinolyloxy group, 4- {4- [2- (4-trifluoromethoxy) group Phenyl) ethyl] -1-piperazinyl} -3-quinolyloxy group, 5- {4- [3- (4-trifluoromethoxyphenyl) propyl] -1-piperazinyl] -4-quinolyloxy group, 6- {4- [4 4- (4-trifluoromethoxyphenyl) butyl] -1-piperazinyl} -5-quinolyloxy group, 7- {4- [5 (4-trifluoromethoxyphenyl) pentyl] -1-piperazinyl} -6-quinolyloxy group, 8- {4- [6- (4-trifluoromethoxyphenyl) hexyl] -1-piperazinyl} -7-quinolyloxy group, 2- {4- [2- (4-trifluoromethylphenyl) ethyl] -1-piperazinyl} -8-quinolyloxy group, 3- {4- [3- (4-trifluoromethylphenyl) propyl] -1- Piperazinyl} -2-quinolyloxy, 4- {4- [4- (4-trifluoromethylphenyl) butyl] -1-piperazinyl} -2-quinolyloxy, 5- {4- [5- (4-trifluoro] Methylphenyl) pentyl] -1-piperazinyl} -2-quinolyloxy group, 6- {4- [6- (4-trifluoromethylphenyl) hexyl -1-piperazinyl} -2-quinolyloxy group, 3- (2-piperidyl) -2-quinolyloxy group, 4- (3-piperidyl) -3-quinolyloxy group, 5- (4-piperidyl) -4-quinolyloxy group , 6- (2,4-diamino-1-piperidyl) -5-quinolyloxy group, 7- (2,4,6-triamino-1-piperidyl) -6-quinolyloxy group, 8- (4-amino-1- Piperidyl) -7-quinolyloxy, 2- (4-amino-1-piperidyl) -8-quinolyloxy, 3- (4-amino-1-piperidyl) -2-quinolyloxy, 4- (4-methylamino- 1-piperidyl) -3-quinolyloxy group, 5- (4-ethylamino-1-piperidyl) -4-quinolyloxy group, 6- (4-n-propylamino-1-piperidyl) 5-quinolyloxy group, 7- (4-dimethylamino-1-piperidyl) -6-quinolyloxy group, 8- (4-diethylamino-1-piperidyl) -7-quinolyloxy group, 2- (4-di-n-propyl) group Amino-1-piperidyl) -8-quinolyloxy group, 3- (4-phenylamino-1-piperidyl) -2-quinolyloxy group, 4- [4- (N-phenyl-N-methylamino) -1-piperidyl] -3-quinolyloxy group, 5- [4- (2-fluorophenylamino) -1-piperidyl] -4-quinolyloxy group, 6- [4- (3-fluorophenylamino) -1-piperidyl] -5-quinolyloxy Group, 7- [4- (4-fluorophenylamino) -1-piperidyl] -6-quinolyloxy group, 8- [4- (2-chlorophenylamino) 1-piperidyl] -7-quinolyloxy group, 2- [4- (3-chlorophenylamino) -1-piperidyl] -8-quinolyloxy group, 3- [4- (4-chlorophenylamino) -1-piperidyl] -2 -Quinolyloxy group, 4- [4- (2,3-dichlorophenylamino) -1-piperidyl] -3-quinolyloxy group, 5- [4- (2,4,6-trifluorophenylamino) -1-piperidyl] -4-quinolyloxy group, 6- [4- (2,4-dichlorophenylamino) -1-piperidyl] -5-quinolyloxy group, 7- [4- (3,4-dichlorophenylamino) -1-piperidyl] -6 -Quinolyloxy group, 8- [4- (3,5-dichlorophenylamino) -1-piperidyl] -7-quinolyloxy group, 2- [4- (2,3,4,5,5 6-pentafluorophenylamino) -1-piperidyl] -8-quinolyloxy group, 3- [4- (2-trifluoromethylphenylamino) -1-piperidyl] -2-quinolyloxy group, 4- [4- (2) -Methylphenylamino) -1-piperidyl] -3-quinolyloxy group, 5- [4- (2,3-dimethylphenylamino) -1-piperidyl] -4-quinolyloxy group, 6- [4- (2-trilyl] group Fluoromethylphenylamino) -1-piperidyl] -5-quinolyloxy group, 7- [4- (2,4,6-trimethylphenylamino) -1-piperidyl] -6-quinolyloxy group, 8- [4- (4) -Trifluoromethylphenylamino) -1-piperidyl] -7-quinolyloxy group, 2- [4- (2-pentafluoroethylphenylamino) -1 Piperidyl] -8-quinolyloxy, 3- [4- (3-pentafluoroethylphenylamino) -1-piperidyl] -2-quinolyloxy, 4- [4- (4-pentafluoroethylphenylamino) -1-] Piperidyl]}-3-quinolyloxy group, 5- [


4- (2-trifluoromethoxyphenylamino) -1-piperidyl] -4-quinolyloxy group, 6- [4- (2-methoxyphenylamino) -1-piperidyl] -5-quinolyloxy group, 7- [4- (4-methoxy) phenyl] (2,3-Dimethoxyphenylamino) -1-piperidyl] -6-quinolyloxy group, 8- [4- (2,4,6-trimethoxyphenylamino) -1-piperidyl] -7-quinolyloxy group, 2- {4- [N-Methyl-N- (2,4,6-trimethoxyphenylamino)]-1-piperidyl} -8-quinolyloxy group, 3- {4- [N-methyl-N- (3,4 -Dimethylphenylamino)]-1-piperidyl} -2-quinolyloxy group, 4- [4- (3-trifluoromethoxyphenylamino) -1-piperidyl] -2-quinolyloxy group, -[4- (4-trifluoromethoxyphenylamino) -1-piperidyl] -2-quinolyloxy group, 6- [4- (2-pentafluoroethoxyphenylamino) -1-piperidyl] -2-quinolyloxy group, 7 -[4- (3-pentafluoroethoxyphenylamino) -1-piperidyl] -2-quinolyloxy group, 8- [4- (4-pentafluoroethoxyphenylamino) -1-piperidyl] -2-quinolyloxy group, 2 -[4- (2-fluorophenylamino) -1-piperidyl] -3-quinolyloxy group, 3- [4- (3-fluorophenylamino) -1-piperidyl] -2-quinolyloxy group, 4- [4- (4-fluorophenylamino) -1-piperidyl] -2-quinolyloxy group, 2- {4- [N-ethyl-N- (4-chloro) Phenyl) amino] -1-piperidyl} -6-quinolyloxy, 2,4-di (1-piperazinyl) -6-quinolyloxy, 3- (1-piperidyl) -4- (1-piperazinyl) -2-quinolyloxy Group, 2,4,6-tri (1-piperidyl) -3-quinolyloxy group, 5-chloro-8-quinolyloxy group, 2- (4-trifluoromethoxyphenoxy) -6-quinolyloxy group, 2- [4-] (4-Trifluoromethoxybenzylidene) -1-piperidyl] -6-quinolyloxy group, 2- [4- (4-chlorobenzylidene) -1-piperidyl] -6-quinolyloxy group, 2- [4- (4-trilyl] group Fluoromethylbenzylidene) -1-piperidyl] -6-quinolyloxy group, 2- (4-benzyl-1-piperidyl) -4-quinolyloxy group, 2 -(3,4-dibenzyl-1-piperidyl) -4-quinolyloxy group, 5- (2,3,4-tribenzyl-1-piperidyl) -2-quinolyloxy group, 4- [4- (2-phenethyl)- 1-piperidyl] -2-quinolyloxy group, 4- [4- (3-phenylpropyl) -1-piperidyl] -5-quinolyloxy group, 4- [4- (4-phenylbutyl) -1-piperidyl] -6 -Quinolyloxy group, 4- [4- (5-phenylpentyl) -1-piperidyl] -7-quinolyloxy group, 2- [4- (6-phenylhexyl) -1-piperidyl] -4-quinolyloxy group, 4- [4- (2-Fluorobenzyl) -1-piperidyl] -2-quinolyloxy group, 2- [4- (3-fluorobenzyl) -1-piperidyl] -4-quinolyloxy group, 2- [ -(4-fluorobenzyl) -1-piperidyl] -5-quinolyloxy group, 2- [4- (2-chlorobenzyl) -1-piperidyl] -6-quinolyloxy group, 2- [4- (3-chlorobenzyl] group ) -Piperidyl] -7-quinolyloxy group, 5- [4- (4-chlorobenzyl) -1-piperidyl] -4-quinolyloxy group, 6- [4- (2,3-dichlorobenzyl) -1-] Piperidyl] -4-quinolyloxy, 7- [4- (2,4-dichlorobenzyl) -1-piperidyl] -8-quinolyloxy, 2- [4- (3,4-dichlorobenzyl) -1-piperidyl] -8-quinolyloxy group, 4- [4- (3,5-dichlorobenzyl) -1-piperidyl] -2-quinolyloxy group, 4- [4- (3,4,5-trichlorobenzyl) -1-pipe Jyl] -5-quinolyloxy group, 4- [4- (2,3,4,5,6-pentafluorobenzyl) -1-piperidyl] -2-quinolyloxy group, 4- [4- (2-trifluoromethyl) group Benzyl) -1-piperidyl] -6-quinolyloxy group, 4- [4- (3-trifluoromethylbenzyl) -1-piperidyl] -7-quinolyloxy group, 2- [4- (4-trifluoromethylbenzyl) group -1-piperidyl] -8-quinolyloxy group, 5- [4- (4-methylbenzyl) -1-piperidyl] -4-quinolyloxy group, 6- [4- (3,4-dimethylbenzyl) -1-piperidyl ] 4-quinolyloxy group, 8- [4- (2,4,6-trimethylbenzyl) -1-piperidyl] -4-quinolyloxy group, 3- [4- (2-pentafluoroethyl ben] Dyl) -1-piperidyl] -2-quinolyloxy group, 8- [4- (3-pentafluoroethyl benzyl) -1-piperidyl] -5-quinolyloxy group, 4- [4- (4-pentafluoroethyl benzyl) -1-piperidyl] -6-quinolyloxy group, 4- [4- (2-trifluoromethoxybenzyl) -1-piperidyl] -7-quinolyloxy group, 5- [4- (3-trifluoromethoxybenzyl) -1 -Piperidyl] -4-quinolyloxy group, 6- [4- (4-trifluoromethoxybenzyl) -1-piperidyl] -5-quinolyloxy group, 7- [4- (4-methoxybenzyl) -1-piperidyl]- 5-quinolyloxy group, 6- [4- (3,4-dimethoxybenzyl) -1-piperidyl] -4-quinolyloxy group, 7- [4- (2,4,6 -Trimethoxybenzyl) -1-piperidyl] -4-quinolyloxy group, 5- [4- (2-pentafluoroethoxybenzyl) -1-piperidyl] -4-quinolyloxy group, 4- [4- (3-pentafluoro] group Ethoxybenzyl) -1-piperidyl] -2-quinolyloxy, 6- [4- (4-pentafluoroethoxybenzyl) -1-piperidyl] -4-quinolyloxy, 4- {4- [2- (4-tri) Fluoromethoxyphenyl) ethyl] -1-piperidyl} -2-quinolyloxy group, 4- {4- [3- (4-trifluoromethoxyphenyl) propyl] -1-piperidyl} -2-quinolyloxy group, 4- {4 -[4- (4-trifluoromethoxyphenyl) butyl] -1-piperidyl} -2-quinolyloxy group, 4- {4- [5- (4) Trifluoromethoxyphenyl) pentyl] -1-piperidyl} -3-quinolyloxy group, 4- {4- [6- (4-trifluoromethoxyphenyl) hexyl] -1-piperidyl} -3-quinolyloxy group, 4- {4 4- [2- (4-trifluoromethylphenyl) ethyl] -1-piperidyl} -2-quinolyloxy group, 5- {4- [3- (4-trifluoromethylphenyl) propyl] -1-piperidyl}- 2-quinolyloxy group, 6- {4- [4- (4-trifluoromethylphenyl) butyl] -1-piperidyl} -2-quinolyloxy group, 7- {4- [5- (4-trifluoromethylphenyl) group Pentyl] -2-piperidyl} -2-quinolyloxy group, 5- {4- [6- (4-trifluoromethylphenyl) hexyl] -1-piperidyl } 2-quinolyloxy group, 2- (4-phenoxy-1-piperidyl) -4-quinolyloxy group, 2- (3,4-diphenoxy-1-piperidyl) -4-quinolyloxy group, 5- (2,3,3 4-triphenoxy-1-piperidyl) -2-quinolyloxy group, 4- [4- (2-fluorophenoxy) -1-piperidyl] -2-quinolyloxy group, 2- [4- (3-fluorophenoxy) -1 -Piperidyl] -4-quinolyloxy group, 2- [4- (4-fluorophenoxy) -1-piperazinyl] -5-quinolyloxy group, 2- [4- (2-chlorophenoxy) -1-piperidyl] -6- Quinolyloxy group, 2- [4- (3-chlorophenoxy) -1-piperidyl] -7-quinolyloxy group, 5- [4- (4-chlorophenoxy) -1-piperidine ] 4-quinolyloxy group, 6- [4- (2,3-dichlorophenoxy) -1-piperidyl] -4-quinolyloxy group, 7- [4- (2,4-dichlorophenoxy) -1-piperidyl]- 4-quinolyloxy group, 2- [4- (3,4-dichlorophenoxy) -1-piperidyl] -8-quinolyloxy group, 4- [4- (3,5-dichlorophenoxy) -1-piperidyl] -2- Quinolyloxy group, 4- [4- (3,4,5-trichlorophenoxy) -1-piperidyl] -5-quinolyloxy group, 4- [4- (2,3,4,5,6-pentafluorophenoxy)- 1-piperidyl] -2-quinolyloxy group, 4- [4- (2-trifluoromethylphenoxy) -1-piperidyl] -6-quinolyloxy group, 4- [4- (3-trifluoromethyl] group Phenoxy) -1-piperidyl] -7-quinolyloxy group, 2- [4- (4-trifluoromethylphenoxy) -1-piperidyl] -4-quinolyloxy group, 5- [4- (4-methylphenoxy) -1 -Piperidyl] -4-quinolyloxy group, 6- [4- (3,4-dimethylphenoxy) -1-piperidyl] -4-quinolyloxy group, 7- [4- (2,4,6-trimethylphenoxy) -1 -Piperidyl] -4-quinolyloxy group, 4- [4- (2-pentafluoroethyl phenoxy) -1-piperidyl] -2-quinolyloxy group, 4- [4- (3-pentafluoroethyl phenoxy) -1-piperidyl ] 5-quinolyloxy group, 4- [4- (4-pentafluoroethylphenoxy) -1-piperidyl] -6-quinolyloxy group, 4- [4- (2-trifluoromethoxyphenoxy) -1-piperidyl] -7-quinolyloxy group, 5- [4- (3-trifluoromethoxyphenoxy) -1-piperidyl] -4-quinolyloxy group, 6- [4- (4) -Trifluoromethoxyphenoxy) -1-piperidyl] -5-quinolyloxy, 7- [4- (4-methoxyphenoxy) -1-piperidyl] -5-quinolyloxy, 6- [4- (3,4-dimethoxy] Phenoxy) -1-piperidyl] -4-quinolyloxy, 8- [4- (2,4,6-trimethoxyphenoxy) -1-piperidyl] -4-quinolyloxy, 5- [4- (2-pentafluoro] Ethoxyphenoxy) -1-piperidyl] -4-quinolyloxy group, 4- [4- (3-pentafluoroethoxyphenoxy) -1-piperi [L] -quinolyloxy group, 6- [4- (4-pentafluoroethoxyphenoxy) -1-piperidyl] -4-quinolyloxy group, 2,5,6-triphenoxy-7-quinolyloxy group, 4,5, 6-trichloro-2-quinolyloxy group, 2-phenoxy-6-bromo-5-quinolyloxy group, 2- (2,3-dimethylphenoxy) -5-quinolyloxy group, 2- (3,4,5-trimethylphenoxy) group -6-quinolyloxy group, 2- (2,3-dimethoxyphenoxy) -7-quinolyloxy group, 2- (3,4,5-trimethoxyphenoxy) -8-quinolyloxy group, 2- (2,3,4, 5,6-Pentafluorophenoxy) -6-quinolyloxy group, 2- (2-methylphenoxy) -4-quinolyloxy group, 2- (3-methylpheno) C) 3-quinolyloxy group, 3- (4-methylphenoxy) -2-quinolyloxy group, 4- (2-methoxyphenoxy) -3-quinolyloxy group, 5- (3-methoxyphenoxy) -4-quinolyloxy group, 6- (4-methoxyphenoxy) -5-quinolyloxy group, 7- (2-fluorophenoxy) -6-quinolyloxy group, 8- (3-fluorophenoxy) -7-quinolyloxy group, 2- (4-fluorophenoxy) group -5-quinolyloxy group, 3- (2-chlorophenoxy) -2-quinolyloxy group, 4- (3-chlorophenoxy) -6-quinolyloxy group, 5- (4-chlorophenoxy) -2-quinolyloxy group, 6- (2-bromophenoxy) -3-quinolyloxy group, 7- (3-bromophenoxy) -4-quinolyloxy group, 8 -(4-bromophenoxy) -2-quinolyloxy group, 2- (2,3-dichlorophenoxy) -6-quinolyloxy group, 3- (3,4-dichlorophenoxy) -7-quinolyloxy group, 4- (2, 2, 2- 4-dichlorophenoxy) -5-quinolyloxy group, 2- (3,4,5-


Trichlorophenoxy) -6-quinolyloxy group, 2- (2,4,6-trichlorophenoxy) -5-quinolyloxy group, 2- (3-trifluoromethylphenoxy) 7-quinolyloxy group, 2- {4- [3-] (4-Trifluoromethylphenyl) -2-propenyl]-(1-, 2- or 3-) piperazinyl}-(3-, 4-, 5-, 6-, 7- or 8-) quinolyloxy group, 2 -[4- (4-methoxyphenyl)-(1-, 2- or 3-) piperazinyl]-(3-, 4-, 5-, 6-, 7- or 8-) quinolyloxy group, 2- [4 -(3,4-Dimethylphenyl)-(1-, 2- or 3-) piperazinyl]-(3-, 4-, 5-, 6-, 7- or 8-) quinolyloxy group, 2- [4-] (4-fluorophenyl)-(1-, 2- or 3-) pi Razinyl]-(3-, 4-, 5-, 6-, 7- or 8-) quinolyloxy group, 2- [4- (4-trifluoromethylphenyl)-(1-, 2- or 3-) piperazinyl ]-(3-, 4-, 5-, 6-, 7- or 8-) quinolyloxy group, 2- [4- (4-methylphenyl)-(1-, 2- or 3-) piperazinyl]-( 3-, 4-, 5-, 6-, 7- or 8-) quinolyloxy group, 2- [4- (3,4-dichlorophenyl)-(1-, 2- or 3-) piperazinyl]-(3- 4-, 5-, 6-, 7- or 8-) quinolyloxy group, 2- [4- (4-trifluoromethoxyphenyl)-(1-, 2- or 3-) piperazinyl]-(3-, 4-, 5-, 6-, 7- or 8-) quinolyloxy group, 2- {4- [4- (4-chlorophenoxy) group -(1-, 2- or 3-) piperazinyl}-(3-, 4-, 5-, 6-, 7- or 8-) quinolyloxy group, 2- [4- (3,4-dichlorobenzyl) Oxy)-(1-, 2- or 3-) piperidyl]-(3-, 4-, 5-, 6-, 7- or 8-) quinolyloxy group, 2- [4- (4-methylbenzyloxy) -(1-, 2- or 3-) piperidyl]-(3-, 4-, 5-, 6-, 7- or 8-) quinolyloxy group, 2- [4- (4-trifluoromethoxybenzyloxy) -(1-, 2- or 3-) piperidyl]-(3-, 4-, 5-, 6-, 7- or 8-) quinolyloxy group, 2- [4- (4-methoxyphenyl)-(1 -, 2- or 3-) piperidyl]-(3-, 4-, 5-, 6-, 7- or 8-) quinolyloxy group, 2- [4- (3,4-Dichlorophenyl)-(1-, 2- or 3-) piperidyl]-(3-, 4-, 5-, 6-, 7- or 8-) quinolyloxy group, 2- {4-[( 1- or 2-) Naphthylmethyl]-(1-, 2- or 3-) piperidinyl}-(3-, 4-, 5-, 6-, 7- or 8-) quinolyloxy group, 2- [4-] (3,4-methylenedioxyphenyl)-(1-, 2- or 3-) piperidyl]-(3-, 4-, 5-, 6-, 7- or 8-) quinolyloxy group, 2- [4 -(4-chlorobenzyloxy)-(1-, 2- or 3-) piperidyl]-(3-, 4-, 5-, 6-, 7- or 8-) quinolyloxy group such as quinolyloxy group (quinoline ring Above, (c-1) halogen atom, (c-2) phenoxy group (on the phenyl ring, halogen atom, halogen substituted or not 1 to 5, preferably 1 to 3 groups selected from the group consisting of a substituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted, (c- 3) Piperazinyl group [on a piperazine ring, a phenyl C.sub.1-6 alkyl group (on a phenyl ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group Group selected from the group consisting of 1 to 5 groups, preferably 1 to 3 groups, phenyl group (on the phenyl ring, phenoxy group [on the phenyl ring, halogen atom, halogen One to five, preferably one to three groups selected from the group consisting of a substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted] 1 to 5, preferably 1 to 3 groups selected from the group consisting of halogen atoms, halogen-substituted or unsubstituted C1-6 alkyl groups and halogen-substituted or unsubstituted C1-6 alkoxy groups are substituted, And an alkenyl group having 2 to 6 carbon atoms and having at least 1 to 3 double bonds, and including both a trans form and a cis form [a phenyl alkenyl group on a phenyl ring, a halogen atom, a halogen 1-5, preferably 1 to 3 groups selected from the group consisting of substituted or unsubstituted C1-6 alkyl groups and halogen-substituted or unsubstituted C1-6 alkoxy groups] And a group selected from the group may be substituted with 1 to 3 groups) and (c-4) piperidyl group [in the piperidine ring, an amino group (on the amino group, a phenyl group [phenyl ring 1 to 5, preferably 1 to 3 groups selected from the group consisting of halogen atoms, halogen-substituted or unsubstituted C1-6 alkyl groups and halogen-substituted or unsubstituted C1-6 alkoxy groups And one to two groups selected from the group consisting of C1-6 alkyl groups may be substituted), phenoxy groups (on the phenyl ring, halogen atoms, halogen substituted or unsubstituted 1 to 5, preferably 1 to 3 groups selected from the group consisting of C1-6 alkyl groups and halogen-substituted or unsubstituted C1-6 alkoxy groups, and phenyl C1-6, An alkyl group (on a phenyl ring, a linear or branched alkylenedioxy group having 1 to 4 carbon atoms, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted 1 to 5, preferably 1 to 3, groups selected from the group consisting of substituted C1-6 alkoxy groups may be substituted), and the alkoxy moiety is a linear or branched chain having 1 to 6 carbon atoms C1-6 alkoxy group which is an alkoxy group (on the phenyl ring, selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group 1 to 5, preferably 1 to 3 substituted groups, a phenyl group (on the phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or not substituted group). 1 to 5, preferably 1 to 3 groups selected from the group consisting of substituted C1-6 alkoxy groups may be substituted), and the alkyl moiety is a linear or branched chain having 1 to 6 carbon atoms Condition And the phenyl C1-6 alkyl group (a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group on the phenyl ring) And 1 to 3 groups selected from the group consisting of 1 to 5 groups, and preferably 1 to 3 groups may be substituted). 1 to 3 selected groups may be substituted).

  Phenyl C1-6 alkoxy substituted C1-6 alkyl group (on the phenyl ring, selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group And at least one kind of the aforementioned groups may be substituted) with a group consisting of a halogen atom as defined above, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group A group selected from 1 to 5 and preferably 1 to 3 substituted phenyl C1-6 alkoxy and C1-6 alkyl, such as benzyloxymethyl; , 2-phenylethoxymethyl group, 3-phenylpropoxymethyl group, 2-phenylpropoxymethyl group, 4-phenylbutoxymethyl group Group, 5-phenylpentoxymethyl group, 4-phenylpentoxymethyl group, 6-phenylhexyloxymethyl group, 2-fluorobenzyloxymethyl group, 4-fluorobenzyloxymethyl group, 4-chlorobenzyloxymethyl group, 3-chlorobenzyloxymethyl group, 2-chlorobenzyloxymethyl group, 3,5-dichlorobenzyloxymethyl group, 3,4-dichlorobenzyloxymethyl group, 2- (3-fluorobenzyloxy) ethyl group, 1- (4-fluorobenzyloxy) ethyl group, 3- [2- (2-fluorophenyl) ethoxy] propyl group, 4- [2- (3-fluorophenyl) ethoxy] butyl group, 5- [2- (4- (4-fluorobenzyl) ethoxy] butyl group Fluorophenyl) ethoxy] pentyl group, 6- (2-chlorobenzyloxy) hexyl group, 3-chloro Benzyloxymethyl group, 2- (4-chlorobenzyloxy) ethyl group, 1- (2-fluoro-4-bromobenzyloxy) ethyl group, 3- (4-chloro-3-fluorobenzyloxy) propyl group, 4 -(2,3,4-trichlorobenzyloxy) butyl group, 5- (3,4,5-trifluorobenzyloxy) pentyl group, 6- (2,3,4,5,6-pentafluorobenzyloxy) Hexyl, 2,4,6-trichlorobenzyloxymethyl, 2- (4-isopropylbenzyloxy) ethyl, 1- (4-n-butylbenzyloxy) ethyl, 3- (4-methylbenzyloxy) Propyl group, 4- (2-methylbenzyloxy) butyl group, 5- (3-methylbenzyloxy) pentyl group, 6- (2,4-dimethylbenzyloxy) ]] Hexyl group, 2,3-dimethylbenzyloxymethyl group, 4-methylbenzyloxymethyl group, 4-ethylbenzyloxymethyl group, 3,5-dimethylbenzyloxymethyl group, 4-isopropylbenzyloxymethyl group, 3 -Trifluoromethylbenzyloxymethyl group, 4-trifluoromethylbenzyloxymethyl group, 2-trifluoromethylbenzyloxymethyl group, 2- (2,6-dimethylbenzyloxy) ethyl group, 1- (3,5-) Dimethylbenzyloxy) ethyl group, 3- (2,5-dimethylbenzyloxy) propyl group, 4- (2,4,6-trimethylbenzyloxy) butyl group, 5- (3,5-ditrifluoromethylbenzyloxy) Pentyl group, 6- (4-isopropoxybenzyloxy) hexyl group, 4-n-b Xybenzyloxymethyl group, 4-trifluoromethoxybenzyloxymethyl group, 2-trifluoromethoxybenzyloxymethyl group, 3-trifluoromethoxybenzyloxymethyl group, 3-methoxybenzyloxymethyl group, 2- (4-methoxy Benzyloxy) ethyl group, 1- (2-methoxybenzyloxy) ethyl group, 3- (3-methoxybenzyloxy) propyl group, 4- (2,4-dimethoxybenzyloxy) butyl group, 5- (2,3 -Dimethoxybenzyloxy) pentyl group, 6- (2,6-dimethoxybenzyloxy) hexyl group, 3,5-dimethoxybenzyloxymethyl group, 2- (2,5-dimethoxybenzyloxy) ethyl group, 1- (2 , 4,6-Trimethoxybenzyloxy) ethyl group, 3- (3,5-ditrile) Fluoromethoxybenzyloxy) propyl, 4- (2-isopropoxybenzyloxy) butyl, 5- (3-chloro-4-methoxybenzyloxy) pentyl, 6- (2-chloro-4-trifluoromethoxy Benzyloxy) hexyl group, 3-methyl-4-fluorobenzyloxymethyl group, 2- (4-bromo-3-trifluoromethylbenzyloxy) ethyl group, 1- [2- (2-chlorophenyl) ethoxy] methyl group , 3- [2- (3-chlorophenyl) ethoxy] propyl, 4- [2- (4-chlorophenyl) ethoxy] butyl, 5- [2-trifluoromethylbenzyloxy] pentyl, 6- (3- Trifluoromethylbenzyloxy) hexyl group, 4-trifluoromethylbenzyloxymethyl group, 2- (2-trif Fluoromethoxybenzyloxy) ethyl group, 1- (3-trifluoromethoxybenzyloxy) ethyl group, 3- (4-trifluoromethoxybenzyloxy) propyl group, 4- [2- (2-trifluoromethylphenyl) group Ethoxy] butyl group, 5- [2- (3-trifluoromethylphenyl) ethoxy] pentyl group, 6- [2- (4-trifluoromethylphenyl) ethoxy] hexyl group, [2- (2-trifluoromethoxy) Phenyl) ethoxy] methyl group, 2- [2- (3-trifluoromethoxyphenyl) ethoxy] ethyl group, 1- [2- (4-trifluoromethoxyphenyl) ethoxy] ethyl group, 3- [3- (2) -Trifluoromethylphenyl) propoxy] propyl group, 4- [3- (3-trifluoromethylphenyl) propoxy Butyl group, 5- [3- (4-trifluoromethylphenyl) propoxy] pentyl group, 6- [3- (2-trifluoromethylphenyl) propoxy] hexyl group, [3- (3-trifluoromethoxyphenyl) Propoxy] methyl group, 2- [3- (4-trifluoromethoxyphenyl) propoxy] ethyl group, 1- [4- (3-trifluoromethylphenyl) butoxy] ethyl group, 3- [5- (4-tri- Fluoromethylphenyl) pentoxy] butyl group, 4- [4- (4-trifluoromethylphenyl) pentoxy] butyl group, 5- [4- (4-trifluoromethoxyphenyl) pentoxy] pentyl group, 6- [6- (3-Trifluoromethylphenyl) hexyloxy] hexyl group, [6- (4-trifluoromethylphenyl) hexyl Carboxymethyl] methyl group, and 2- [6- (4-trifluoromethoxyphenyl) hexyloxy] ethyl group or the like.

Piperidyl group [on a piperidine ring, selected from the group consisting of a phenoxy group (on a phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group At least one of the above groups may be substituted, phenyl C.sub.1-6 alkoxy substituted C.sub.1-6 alkyl group (on the phenyl ring, halogen atom, halogen substituted or unsubstituted C.sub.1-6 alkyl group and halogen substituted) Or at least one group selected from the group consisting of unsubstituted C1-6 alkoxy groups may be substituted), phenoxy C1-6 alkyl group (on the phenyl ring, a halogen atom, halogen substituted or not, A small number of groups selected from the group consisting of a substituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group And at least one member may be substituted) and phenyl C1-6 alkyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 At least one group selected from the group consisting of alkoxy group, and at least one group selected from the group consisting of alkoxy groups may be substituted], for example, 1-piperidyl , 4-piperidyl group, 2-piperidyl group, 3-piperidyl group, 4-phenoxy-1-piperidyl group, 2,4-diphenoxy-1-piperidyl group, 2,4,6-triphenoxy-1-piperidyl group , 2- (2-fluorophenoxy) -1-piperidyl group, 3- (3-fluorophenoxy) -2-piperidyl group, 4- (4-fluorophenoxy) -3- Peridyl group, 2- (2-chlorophenoxy) -4-piperidyl group, 3- (3-chlorophenoxy) -5-piperidyl group, 4- (4-chlorophenoxy) -2-piperidyl group, 5- (2-) Bromophenoxy) -2-piperidyl group, 6- (3-bromophenoxy) -3-piperidyl group, 4- (4-bromophenoxy) -1-piperidyl group, 3- (2,3-dichlorophenoxy) -2- Piperidyl group, 4- (3,4-dichlorophenoxy) -3-piperidyl group, 3- (2,4-dichlorophenoxy) -4-piperidyl group, 2- (3,4,5-trichlorophenoxy) -3- Piperidyl group, 6- (2,4,6-trichlorophenoxy) -2-piperidyl group, 3- (2,3,4,5,6-pentafluorophenoxy) -1-piperidyl group, 4- (2- Thilphenoxy) -1-piperidyl group, 5- (3-methylphenoxy) -2-piperidyl group, 6- (4-methylphenoxy) -3-piperidyl group, 3- (2-ethylphenoxy) -4-piperidyl group , 2- (3-ethyl phenoxy) -1-piperidyl group, 3- (4-ethyl phenoxy) -2-piperidyl group, 4- (4-n-propyl phenoxy) -3-piperidyl group, 3- (4 -Tert-Butylphenoxy) -4-piperidyl group, 2- (4-n-butylphenoxy) -3-piperidyl group, 4- (2-trifluoromethylphenoxy) -2-piperidyl group, 2- (3-tributyl group) Fluoromethyl phenoxy) -1-piperidyl group, 3- (4-trifluoromethyl phenoxy) -1-piperidyl group, 1- (2-pentafluoroethyl phenoxy)- -Piperidyl group, 1- (3-pentafluoroethyl phenoxy) -4-piperidyl group, 4- (2,3-dimethylphenoxy) -1-piperidyl group, 3- (3,4,5-trimethylphenoxy) -4 -Piperidyl group, 1- (4-n-pentylphenoxy) -4-piperidyl group, 4- (4-n-hexylphenoxy) -1-piperidyl group, 4- (2-methoxyphenoxy) -1-piperidyl group, 1- (3-methoxyphenoxy) -4-piperidyl group, 3- (4-methoxyphenoxy) -4-piperidyl group, 2- (2-ethoxyphenoxy) -3-piperidyl group, 3- (3-ethoxyphenoxy) -4-piperidyl group, 4- (4-ethoxyphenoxy) -3-piperidyl group, 3- (4-n-propoxyphenoxy) -2-piperidyl group, 2- (4 tert-Butoxyphenoxy) -1-piperidyl group, 4- (4-n-butoxyphenoxy) -2-piperidyl group, 2- (2-trifluoromethoxyphenoxy) -3-piperidyl group, 3- (3-trifluoro Methoxyphenoxy) -4-piperidyl group, 4- (4-trifluoromethoxyphenoxy) -3-piperidyl group, 3- (2-pentafluoroethoxyphenoxy) -2-piperidyl group, 2- (4-pentafluoroethoxyphenoxy) group ) -L-Piperidyl group, 3- (2,3-dimethoxyphenoxy) -4-piperidyl group, 4- (3,4,5-trimethoxyphenoxy) -1-piperidyl group, 4- (4-n-pentyl) group Oxyphenoxy) -1-piperidyl group, 4- (4-n-hexyloxyphenoxy) -1-piperidyl group, 4-benzylene Le-1-piperidyl group, 2,4-dibenzyl-1-piperidyl group, 2,4,6-tribenzyl-1-piperidyl group, 2- (2-fluorobenzyl) -1-piperidyl group, 3- [2- (3-fluorophenyl) ethyl] -2-piperidyl group, 4- [1- (4-fluorophenyl) ethyl] -3-piperidyl group, 2- [3- (2-chlorophenyl) propyl] -4-piperidyl group 3- [4- (3-chlorophenyl) butyl] -5-piperidyl group, 4- [5- (4-chlorophenyl) pentyl] -2-piperidyl group, 5-([6- (2-bromophenyl) hexyl] ] -2-piperidyl group, 6- (3-bromobenzyl) -3-piperidyl group, 4- (4-bromobenzyl) -1-piperidyl group, 3- (2,3-dichlorobenzyl) -2-piperidyl group 4- (3,4-dichlorobenzyl) -3-piperidyl group, 3- (2,4-dichlorobenzyl) -4-piperidyl group, 2- (3,4,5-trichlorobenzyl) -3-piperidyl group, 6- (2,4,6-trichlorobenzyl) -2-piperidyl group, 3- (2,3,4,5,6-pentafluorobenzyl) -1-piperidyl group, 4- (2-methylbenzyl)- 1-piperidyl group, 5- [2- (3-methylphenyl) ethyl] -2-piperidyl group, 6- [3- (4-methylphenyl) propyl] -3-piperidyl group, 1- [4- (2) -Ethylphenyl) butyl] -4-piperidyl group, 2- [5- (3-ethylphenyl) pentyl] -1-piperidyl group, 3- [6- (4-ethylphenyl) hexyl] -2-piperidyl group, 4- (4-n-propyl) N'diyl) -3-piperidyl group, 3- (4-tert-butylbenzyl) -4-piperidyl group, 2- (4-n-butylbenzyl) -3-piperidyl group, 1- (2-trifluoromethylbenzyl) -2-piperidyl group, 2- (3-trifluoromethylbenzyl) -1-piperidyl group, 4- (4-trifluoromethylbenzyl) -1-piperidyl group, 1- (2-pentafluoroethyl benzyl) -4 -Piperidyl group, 1- (3-pentafluoroethylbenzyl) -4-piperidyl group, 4- (2,3-dimethylbenzyl) -1-piperidyl group, 1- (3,4,5-trimethylbenzyl) -4 -Piperidyl group, 1- (4-n-pentylbenzyl) -4-piperidyl group, 4- (4-n-hexylbenzyl) -1-piperidyl group, 4- (2-methoxybenzyl) L) -Piperidyl group, 1- [2- (3-methoxyphenyl) ethyl] -4-piperidyl group, 1- [1- (4-methoxyphenyl) ethyl] -4-piperidyl group, 2- [3 -(2-ethoxyphenyl) propyl] -3-piperidyl group, 3- [4- (3-ethoxyphenyl) butyl] -4-piperidyl group, 4- [5- (4-ethoxyphenyl) pentyl] -3- Piperidyl group, 3- [6- (4-n-propoxyphenyl) hexyl-2-piperidyl group, 2- (4-tert-butoxybenzyl) -1-piperidyl group, 1- (4-n-butoxybenzyl)- 2-piperidyl group, 2- (2-trifluoromethoxybenzyl) -3-piperidyl group, 3- (3-trifluoromethoxybenzyl) -4-piperidyl group, 4- (4-trifluoromethoxy) Nidyl) -1-piperidyl group, 3- (2-pentafluoroethoxybenzyl) -2-piperidyl group, 2- (4-pentafluoroethoxybenzyl) -1-piperidyl group, 1- (2,3-dimethoxybenzyl) group -4-piperidyl group, 4- (3,4,5-trimethoxybenzyl) -1-piperidyl group, 4- (4-n-pentyloxybenzyl) -1-piperidyl group, 4- (4-n-hexyl) group Oxybenzyl) -1-piperidyl group, 4-benzyl-3-phenoxy-1-piperidyl group, 4-benzyloxymethyl-1-piperidyl group, 2,4-dibenzyloxymethyl-1-piperidyl group, 2,4 , 6-tribenzyloxymethyl-1-piperidyl group, 2-[(2-fluorobenzyloxy) methyl] -1-piperidyl group, 3- {2- [2- (3) Fluorophenyl) ethoxy] ethyl} -2-piperidyl group, 4- {1- [1- (4-fluorophenyl) ethyl] ethoxy} -3-piperidyl group, 2- {3- [3- (2-chlorophenyl) group Propoxy] propyl} -4-piperidyl group, 3- {4- [4- (3-chlorophenyl) butoxy] butyl} -5-piperidyl group, 4- {5- [5- (4-chlorophenyl) pentyloxy] pentyl } -2-Piperidyl group, 5- {6- [6- (2-bromophenyl) hexyloxy] -2-piperidyl group, 6- (3-bromobenzyloxymethyl) -3-piperidyl group, 4- (4) -Bromobenzyloxymethyl) -1-piperidyl group, 3- (2,3-dichlorobenzyloxymethyl) -2-piperidyl group, 4- (3,4-dichlorobenzyloxyme) Ethyl) -3-piperidyl group, 3- (2,4-dichlorobenzyloxymethyl) -4-piperidyl group, 2- (3,4,5-trichlorobenzyloxymethyl) -3-piperidyl group, 6- (2) , 4,6-Trichlorobenzyloxymethyl) -2-piperidyl group, 3- (2,3,4,5,6-pentafluorobenzyloxymethyl) -1-piperidyl group, 4- (2-methylbenzyloxymethyl) ) -L-Piperidyl group, 5- {2- [2- (3-methylphenyl) ethoxy] ethyl} -2-piperidyl group, 6- {3- [3- (4-methylphenyl) propoxy] propyl}- 3-piperidyl group, 1- {4- [4- (2-ethylphenyl) butoxy] butyl} -4-piperidyl group, 2- {5- [5- (3-ethylphenyl) pentyloxy] pentyl} 1-piperidyl group, 3- {6- [6- (4-ethylphenyl) hexyloxy] hexyl} -2-piperidyl group, 4- (4-n-propylbenzyloxymethyl) -3-piperidyl group, 3- (4-tert-butylbenzyloxymethyl) -4-piperidyl group, 2- (4-n-butylbenzyloxymethyl) -3-piperidyl group, 1- (2-trifluoromethylbenzyloxymethyl) -2-piperidyl Group, 2- (3-trifluoromethylbenzyloxymethyl) -1-piperidyl group, 4- (4-trifluoromethylbenzyloxymethyl) -1-piperidyl group, 1- (2-pentafluoroethyl benzyloxymethyl) -4-piperidyl group, 1- (3-pentafluoroethylbenzyloxymethyl) -4-piperidyl group, 4- (2,3-) Methylbenzyloxymethyl) -1-piperidyl group, 1- (3,4,5-trimethylbenzyloxymethyl) -4-piperidyl group, 1- (4-n-pentylbenzyloxymethyl) -4-piperidyl group, 4 -(4-n-hexylbenzyloxymethyl) -1-piperidyl group, 4- (2-methoxybenzyloxymethyl) -1-piperidyl group, 1- {2- [2- (3-methoxyphenyl) ethoxy] ethyl } -4-Piperidyl group, 1- {1- [1- (4-methoxyphenyl) ethoxy] ethyl} -4-piperidyl group, 2- {3- [3- (2-ethoxyphenyl) propoxy] propyl}- 3-piperidyl group, 3- {4- [4- (3-ethoxyphenyl) butoxy] butyl-4-piperidyl group, 4- {5- [5- (4-ethoxyphenyl) penty] group Roxy] pentyl} -3-piperidyl group, 3- {6- [6- (4-n-propoxyphenyl) hexyloxy] hexyl} -2-piperidyl group, 2- (4-tert-butoxybenzyloxymethyl)- 1-piperidyl group, 1- (4-n-butoxybenzyloxyme)




4- (4-Trifluoromethoxybenzyloxymethyl) -4-piperidyl group; 4- (4-tridochloro); 2- (2-trifluoromethoxybenzyloxymethyl) -3-piperidyl group; 3- (3-trifluoromethoxybenzyloxymethyl) -4-piperidyl group Fluoromethoxybenzyloxymethyl) -1-piperidyl group, 3- (2-pentafluoroethoxybenzyloxymethyl) -2-piperidyl group, 2- (4-pentafluoroethoxybenzyloxymethyl) -1-piperidyl group, 1- (2,3-Dimethoxybenzyloxymethyl) -4-piperidyl group, 4- (3,4,5-trimethoxybenzyloxymethyl) -1-piperidyl group, 4- (4-n-pentyloxybenzyloxymethyl) -1-piperidyl group, 4- (4-n-hexyloxybenzyloxymethyl) -1-piperidyl group 4-benzyloxymethyl-3-phenoxy-1-piperidyl group, 4-benzyl-3-phenoxy-1-piperidyl group, 4- (4-chlorophenoxymethyl)-(1-, 2- or 3-) piperidyl group And the like. On the piperidine ring (from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group, and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group). 1 to 5, preferably 1 to 3 selected groups may be substituted; phenyl C1 to 6 alkoxy substituted C1 to 6 alkyl groups (on the phenyl ring, halogen atoms, halogen substituted or unsubstituted) 1 to 5 groups, preferably 1 to 3 groups, selected from the group consisting of C1-6 alkyl groups of the above and halogen-substituted or unsubstituted C1-6 alkoxy groups Phenoxy C1-6 alkyl group in which the alkyl moiety is a linear or branched alkyl group having 1 to 6 carbon atoms (a halogen atom, a halogen-substituted or unsubstituted C 1 on the phenyl ring) 1 to 5, preferably 1 to 3 groups selected from the group consisting of -6 alkyl group and halogen substituted or unsubstituted C1-6 alkoxy group may be substituted) and phenyl C1-6 alkyl group (On the phenyl ring, 1 to 5 groups, preferably 1 group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group are preferable. And the group selected from the group consisting of -3 each may be substituted.

  A benzothienyl C1-6 alkyl group (on the benzothiophene ring, a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group As at least one kind of the substituent, for example, [(2-, 3-, 4-, 5-, 6- or 7-) benzothienyl] methyl group, 1-[(2-, 3- , 4-, 5-, 6- or 7-) benzothienyl] ethyl group, 2-[(2-, 3-, 4-, 5-, 6- or 7-) benzothienyl] ethyl group, 3- [ (2-, 3-, 4-, 5-, 6- or 7-) benzothienyl] propyl group, 2-[(2-, 3-, 4-, 5-, 6- or 7-) benzothienyl] Propyl group, 4-[(2-, 3-, 4-, 5-, 6- or 7-) benzothienyl] Group, 5-[(2-, 3-, 4-, 5-, 6- or 7-) benzothienyl] pentyl group, 4-[(2-, 3-, 4-, 5-, 6- or 7-) benzothienyl] pentyl group, 6-[(2-, 3-, 4-, 5-, 6- or 7-) benzothienyl] hexyl group, 2-methyl-3-[(2-, 3- , 4-, 5-, 6- or 7-) benzothienyl] propyl group, 1,1-dimethyl-2-[(2-, 3-, 4-, 5-, 6- or 7-) benzothienyl] Ethyl group, 5-chloro- (2-, 3-, 4-, 6- or 7-) benzothienylmethyl group, 5-methyl- (2-, 3-, 4-, 6- or 7-) benzothienyl Methyl, 5-methoxy- (2-, 3-, 4-, 6- or 7-) benzothienylmethyl, 5-trifluoromethyl- (2-, 3-, 4-, 6- Is 7-) benzothienylmethyl group, 5-trifluoromethoxy- (2-, 3-, 4-, 6- or 7-) benzothienylmethyl group, 5, 6-dichloro- (2-, 3-, 4) -Or 7-) benzothienylmethyl group, 4,5, 6-trifluoro- (2-, 3- or 7-) benzothienylmethyl group, 5-chloro-6-trifluoromethoxy- (2-, 3) -, 4- or 7-) benzothienylmethyl group, 2, 5-dimethyl- (3-, 4-, 6- or 7-) benzothienylmethyl group, 2, 5, 6- trimethyl- (3-, 4) Benzothienyl C1-6 alkyl group wherein the alkyl moiety such as-or 7-) benzothienylmethyl group is a linear or branched alkyl group having 1 to 6 carbon atoms (a halogen atom or halogen on the benzothiophene ring Substituted or unsubstituted C1-6 alkyl And 1 to 3 groups selected from the group consisting of a group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be mentioned.

  A thiazolyl C1-6 alkyl group [in which at least one phenyl group (a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 on a phenyl ring Examples of a group in which at least one group selected from the group consisting of an alkoxy group may be substituted may be substituted with, for example, a [(2-, 4- or 5-) thiazolyl] methyl group 1-[(2-, 4- or 5-) thiazolyl] ethyl group, 2-[(2-, 4- or 5-) thiazolyl] ethyl group, 3-[(2-, 4- or 5-) group Thiazolyl] propyl group, 2-[(2-, 4- or 5-) thiazolyl] propyl group, 4-[(2-, 4- or 5-) thiazolyl] butyl group, 5-[(2-, 4-) Or 5-) thiazolyl] pentyl group, 4-[(2- 4- or 5-) thiazolyl] pentyl group, 6-[(2-, 4- or 5-) thiazolyl] hexyl group, 2-methyl-3-[(2-, 4- or 5-) thiazolyl] propyl group 1,1-dimethyl-2-[(2-, 4- or 5-) thiazolyl] ethyl group, 2- (4-trifluoromethylphenyl)-(4- or 5-) thiazolylmethyl group, 2- (4) -Trifluoromethylphenyl)-(4- or 5-) thiazolylmethyl group, 2- (4-trifluoromethoxyphenyl)-(4- or 5-) thiazolylmethyl group, 4- (3-methylphenyl)-(2-) Or 5-) thiazolyl methyl group, 5- (2-methoxyphenyl)-(2- or 5-) thiazolyl methyl group, 4- (4-chlorophenyl)-(2- or 5-) thiazolyl methyl group, 2- (2, 4) -Jime Phenyl)-(4- or 5-) thiazolylmethyl group, 2- (2,4,6-trimethylphenyl)-(4- or 5-) thiazolylmethyl group, 2- (3,4-dimethoxyphenyl)-(4-) Or 5-) thiazolylmethyl group, 2- (3,4,5-trimethoxyphenyl)-(4- or 5-) thiazolylmethyl group, 2- (3-chloro-4-trifluoromethylphenyl)-(4- or 5-) thiazolylmethyl group, 4- (3,4-dichlorophenyl)-(2- or 5-) thiazolylmethyl group, 2- (3,4,6-trifluorophenyl)-(4- or 5-) thiazolylmethyl group, Thiazolyl C1-6 alkyl group [thiazo wherein the alkyl moiety such as 2,4-diphenyl- (4- or 5-) thiazolyl methyl group is a linear or branched alkyl group having 1 to 6 carbon atoms Group having one to two phenyl groups (on the phenyl ring, a group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group). 1 to 5 groups, and preferably 1 to 3 groups may be substituted) may be substituted.

  Indolyl C1-6 alkyl group (on the indole ring, at least one of the groups selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group The species may be substituted), for example, [(1-, 2-, 3-, 4-, 5-, 6- or 7-) indolyl] methyl group, 1-[(1-, 2 -, 3-, 4-, 5-, 6- or 7-) indolyl] ethyl group, 2-[(1-, 2-, 3-, 4-, 5-, 6- or 7-) indolyl] ethyl Group, 3-[(1-, 2-, 3-, 4-, 5-, 6- or 7-) indolyl] propyl group, 2-[(1-, 2-, 3-, 4-, 5-] , 6- or 7-) indolyl] propyl group, 4-[(1-, 2-, 3-, 4-, 5-, 6- or 7-) indolyl Butyl group, 5-[(1-, 2-, 3-, 4-, 5-, 6- or 7-) indolyl] pentyl group, 4-[(1-, 2-, 3-, 4-, 5 -, 6- or 7-) indolyl] pentyl group, 6-[(1-, 2-, 3-, 4-, 5-, 6- or 7-) indolyl] hexyl group, 2-methyl-3- [ (1-, 2-, 3-, 4-, 5-, 6- or 7-) indolyl] propyl group, 1,1-dimethyl-2-[(1-, 2-, 3-, 4-, 5 -, 6- or 7-) indolyl] ethyl group, 2-trifluoromethyl- (1-, 3-, 4-, 5-, 6- or 7-) indolylmethyl group, 5-trifluoromethyl- ( 1-, 2-, 3-, 4-, 6- or 7-) indolylmethyl group, 2-trifluoromethoxy- (1-, 3-, 4-, 5-, 6- or 7-) indolylme Group 4-methyl- (1-, 2-, 3-, 5-, 6- or 7-) indolylmethyl group, 5-methoxy- (1-, 2-, 3-, 4-, 6- Or 7-) indolylmethyl group, 4-chloro- (1-, 2-, 3-, 5-, 6- or 7-) indolylmethyl group, 2,4-dimethyl- (1-, 3-, 7-) 5-, 6- or 7-) indolylmethyl group, 2,4,6-trimethyl- (1-, 3-, 5- or 7-) indolylmethyl group, 3,4-dimethoxy- (1-, 2-, 5-, 6- or 7-) indolylmethyl group, 3, 4, 5-trimethoxy- (1-, 2-, 6- or 7-) indolylmethyl group, 3-chloro-4-trilo Fluoromethyl- (1-, 2-, 5-, 6- or 7-) indolyl methyl group, 3,4-dichloro- (1-, 2-, 5-, 6- or 7-) indoli Methyl group, 3,4,6-trifluoro- (1-, 2-, 5- or 7-) indolylmethyl group, 5-trifluoromethoxy- (1-, 2-, 3-, 4-, 6 -Or 7-) indolylmethyl group, 5-trifluoromethoxy-6-chloro- (1-, 2-, 3-, 4- or 7-) indolylmethyl group, 1,3-dimethyl-5-fluoro An indolyl C1-6 alkyl group in which the alkyl moiety such as-(2-, 4-, 6- or 7-) indolylmethyl group is a linear or branched alkyl group having 1 to 6 carbon atoms (on an indole ring And the group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted with 1 to 3 It can be mentioned.

  A phenyl C1-6 alkyl group (a group selected from the group consisting of a benzofuryl group, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group on the phenyl ring As the above-mentioned phenyl C1-6 alkyl group (on the phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group, and a halogen-substituted or unsubstituted group. 4-[(2-, 3-, 4-, 5-, 6-, or 7-) in addition to at least one of a group selected from the group consisting of C1-6 alkoxy groups] ) Benzofuryl] benzyl group, 2-[(2-, 3-, 4-, 5-, 6- or 7-) benzofuryl] benzyl group, 3-[(2-, 3-, 4-, 5-, 6) -Or 7-) benzofuryl Benzyl, 3,4-di [(2-, 3-, 4-, 5-, 6- or 7-) benzofuryl] benzyl, 2,4,6-tri [(2-, 3-, 4-) Alkyl moieties such as 5-, 6- or 7-) benzofuryl] benzyl group, 3-chloro-4-[(2-, 3-, 4-, 5-, 6- or 7-) benzofuryl] benzyl group A phenyl C1-6 alkyl group which is a linear or branched alkyl group having 1 to 6 carbon atoms (a benzofuryl group, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted on the phenyl ring Or 1 to 5, preferably 1 to 3 groups selected from the group consisting of unsubstituted C1-6 alkoxy groups may be mentioned.

A pyridyloxy group (a pyridine ring, a (d-1) piperidyl group [a piperidine ring, a phenoxy group (a phenyl atom, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted Or at least one group selected from the group consisting of unsubstituted C1-6 alkoxy groups may be substituted), phenyl C1-6 alkoxy substituted C1-6 alkyl group (a halogen atom on the phenyl ring) , At least one of a group selected from the group consisting of halogen-substituted or unsubstituted C1-6 alkyl groups and halogen-substituted or unsubstituted C1-6 alkoxy groups may be substituted), phenoxy C1-6 alkyl Group (on the phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1-6 group. And at least one of a group selected from the group consisting of a lucoxy group may be substituted) and a phenyl C1-6 alkyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group) And at least one group selected from the group consisting of halogen-substituted or unsubstituted C1-6 alkoxy groups, and at least one group selected from the group consisting of And (d-2) piperazinyl group [C.sub.1-6 alkoxycarbonyl group on piperazine ring, furyl C.sub.1-6 alkyl group [on furan ring, at least one phenyl group (on phenyl ring; At least one selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group [Optionally substituted], pyridyl C1-6 alkyl group [wherein on a pyridine ring, a furyl group and a phenyl group (on a phenyl ring, a halogen atom, halogen substituted or unsubstituted At least one group selected from the group consisting of a group selected from the group consisting of a C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted) Benzothienyl C1-6 alkyl group (on the benzothiophene ring, from a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group At least one of a group selected from the group consisting of: a phenyl C.sub.2-6 alkenyl group (on the phenyl ring, a halogen atom, halogen substitution; Is optionally substituted by at least one group selected from the group consisting of unsubstituted C.sub.1-6 alkyl groups and halogen substituted or unsubstituted C.sub.1-6 alkoxy groups), benzofuryl C.sub.1-6 alkyl groups [benzofuran At least one selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted on the ring A benzofuryl C 2-6 alkenyl group [in the benzofuran ring, a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group At least one type may be substituted], thiazolyl C.sub.1-6 alkyl group [on the thiazole ring, at least one phenyl group Even if at least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group is substituted on the phenyl ring (Optional) may be substituted], phenoxy C1-6 alkyl group (on the phenyl ring, halogen atom, halogen substituted or unsubstituted C1-6 alkyl group and halogen substituted or unsubstituted C1-6 alkoxy group At least one group selected from the group consisting of: an indolyl C.sub.1-6 alkyl group (on the indole ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen) At least one selected from the group consisting of substituted or unsubstituted C1-6 alkoxy groups may be substituted) and phenyl C1-6 alkyl (On the phenyl ring, at least one of a group selected from the group consisting of a benzofuryl group, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group is substituted For example, at least one kind of groups selected from the group consisting of at least one kind of groups selected from the group consisting of , 2-pyridyloxy group, 3-pyridyloxy group, 4-pyridyloxy group, 3- (1-piperidyl) -2-pyridyloxy group, 2- (4-piperidyl) -3-pyridyloxy group, 4- (4- 2-piperidyl) -3-pyridyloxy group, 5- (3-piperidyl) -2-pyridyloxy group, 2,4-di (1-piperidyl) -3-pyridyloxy group, 2- (1-piperidine) ) -4- [2- (2-Fluorophenoxy) -1-piperidyl] -3-pyridyloxy group, 2,4,6-tri (1-piperidyl) -3-pyridyloxy group, 2- (4-phenoxy) group -1-piperidyl) -3-pyridyloxy group, 2- (2,4-diphenoxy-1-piperidyl) -3-pyridyloxy group, 3- (2,4,6-triphenoxy-1-piperidyl) -4 -Pyridyloxy group, 4- [2- (2-fluorophenoxy) -1-piperidyl] -2-pyridyloxy group, 5- [3- (3-fluorophenoxy) -2-piperidyl] -3-pyridyloxy group 6- [4- (4-fluorophenoxy) -3-piperidyl] -4-pyridyloxy group, 2- [2- (2-chlorophenoxy) -4-piperidyl] -3-pyridyloxy group, 3- [4 3- ( 3-chlorophenoxy) -5-piperidyl] -4-pyridyloxy group, 4- [4- (4-chlorophenoxy) -2-piperidyl] -2-pyridyloxy group, 5- [5- (2-bromophenoxy] group ) -2-Piperidyl] -3-pyridyloxy group, 2- [6- (3-bromophenoxy) -3-piperidyl] -4-pyridyloxy group, 2- [4- (4-bromophenoxy) -1-] Piperidyl] -2-pyridyloxy, 3- [3- (2,3-dichlorophenoxy) -2-piperidyl] -4-pyridyloxy, 3- [4- (3,4-dichlorophenoxy) -3- Piperidyl] -4-pyridyloxy, 4- [3- (2,4-dichlorophenoxy) -4-piperidyl] -2-pyridyloxy, 5- [2- (3,4,5-trichlorophenoxy)- 3- Peridyl] -2-pyridyloxy, 6- [6- (2,4,6-trichlorophenoxy) -2-piperidyl] -3-pyridyloxy, 2- [3- (2,3,4,5,5 6-Pentafluorophenoxy) -1-piperidyl] -3-pyridyloxy group, 4- [4- (2-methylphenoxy) -1-piperidyl] -2-pyridyloxy group, 3- [5- (3-methyl] group Phenoxy) -2-piperidyl] -2-pyridyloxy group, 5- [6- (4-methylphenoxy) -3-piperidyl] -3-pyridyloxy group, 2- [1- (2-ethylphenoxy) -4 -Piperidyl] -4-pyridyloxy group, 2- [2- (3-ethylphenoxy) -1-piperidyl] -3-pyridyloxy group, 3- [3- (4-ethylphenoxy) -2-piperidyl]- 4-Piri Ryloxy group, 4- [4- (4-n-propylphenoxy) -3-piperidyl] -2-pyridyloxy group, 5- [5- (4-tert-butylphenoxy) -4-piperidyl] -3-pyridyl Oxy group, 6- [2- (4-n-butylphenoxy) -3-piperidyl] -2-pyridyloxy group, 2- [1- (2-trifluoromethylphenoxy) -2-piperidyl] -4-pyridyl Oxy group, 3- [2- (3-trifluoromethylphenoxy) -1-piperidyl] -4-pyridyloxy group, 4- [3- (4-trifluoromethylphenoxy) -1-piperidyl] -2-pyridyl Oxy group, 5- [1- (2-pentafluoroethyl phenoxy) -4-piperidyl] -3-pyridyloxy group, 6- [1- (3-pentafluoroethyl phenoxy) -4 -Piperidyl] -2-pyridyloxy group, 2- [4- (2,3-dimethylphenoxy) -1-piperidyl] -3-pyridyloxy group, 3- [1- (3,4,5-trimethylphenoxy) group -4-piperidyl] -2-pyridyloxy group, 4- [1- (4-n-pentylphenoxy) -4-piperidyl] -3-pyridyloxy group, 5- [4- (4-n-hexylphenoxy) group -1-piperidyl] -2-pyridyloxy group, 6- [4- (2-methoxyphenoxy) -1-piperidyl] -2-pyridyloxy group, 2- [1- (3-methoxyphenoxy) -4-piperidyl ] 4-pyridyloxy group, 3- [1- (4-methoxyphenoxy) -4-piperidyl] -2-pyridyloxy group, 4- [2- (2-ethoxyphenoxy) -3-piperidyl] -2- Lysyloxy group, 5- [3- (3-ethoxyphenoxy) -4-piperidyl] -3-pyridyloxy group, 2- [4- (4-ethoxyphenoxy) -5-piperidyl] -4-pyridyloxy group, 2 -[3- (4-n-propoxyphenoxy) -2-piperidyl] -4-pyridyloxy group, 3- [2- (4-tert-butoxyphenoxy) -1-piperidyl] -4-pyridyloxy group, 4 -[1- (4-n-butoxyphenoxy) -2-piperidyl] -2-pyridyloxy group, 5- [2- (2-trifluoromethoxyphenoxy) -3-piperidyl] -2-pyridyloxy group, 6 -[3- (3-trifluoromethoxyphenoxy) -4-piperidyl] -2-pyridyloxy group, 6- [4- (4-trifluoromethoxyphenoxy) -3-pipe Jyl] -2-pyridyloxy group, 2- [3- (2-pentafluoroethoxyphenoxy) -2-piperidyl] -3-pyridyloxy group, 3- [4- (4-pentafluoroethoxyphenoxy) -1-] Piperidyl] -2-pyridyloxy group, 4- [1- (2,3-dimethoxyphenoxy) -4-piperidyl] -2-pyridyloxy group, 5- [4- (3,4,5-trimethoxyphenoxy) group -1-piperidyl] -3-pyridyloxy group, 6- [4- (4-n-pentyloxyphenoxy) -1-piperidyl] -3-pyridyloxy group, 5- [4- (4-n-hexyloxy group) Phenoxy) -1-piperidyl] -3-pyridyloxy group, 2- [4- (4-trifluoromethylbenzyloxymethyl) -1-piperidyl] -5-pyridyloxy group, 2- (4-trifluoromethoxybenzyl-1-piperidyl) -5-pyridyloxy group, 2- [4- (4-chlorobenzyl) -1-piperazinyl] -5-pyridyloxy group, 2- [4- (4-) Trifluoromethylbenzyl) -1-piperazinyl] -5-pyridyloxy group, 2- [4- (4-chlorobenzyloxymethyl) -1-piperidyl] -5-pyridyloxy group, 4- (4-fluorobenzyl- 1-piperazinyl) -6-pyridyloxy group, 4-phenoxy-3- [4- (4-trifluoromethoxybenzyloxymethyl) -1-piperidyl] -2-pyridyloxy group, 2- [4-tert-butoxy Carbonyl- (1-, 2- or 3-) piperazinyl]-(3-, 4-, 5- or 6-) pyridyloxy group, 2- [4- {4-[(2-, 3-) 4-, 5-, 6- or 7-) benzofuryl] benzyl}-(1-, 2- or 3-) piperazinyl]-(3-, 4-, 5- or 6-) pyridyloxy group, 2- [ 4- {3-[(2- or 3-) furyl] pyridylmethyl}-(1-, 2- or 3-) piperazinyl]-(3-, 4-, 5- or 6-) pyridyloxy group, 2 -{4- [2- (4-trifluoromethoxyphenyl) pyridylmethyl]-(1-, 2- or 3-) piperazinyl}-(3-, 4-, 5- or 6-) pyridyloxy group, 2 -{4- [2- (3-chloro-4-fluorophenyl) pyridylmethyl]-(1-, 2- or 3-) piperazinyl}-(3-, 4-, 5- or 6-) pyridyloxy group , 2- {4- [5-trifluoromethyl- (2-, 3-, 4-, 6- or 7-) benzo Rylmethyl]-(1-, 2- or 3-) piperazinyl}-(3-, 4-, 5- or 6-) pyridyloxy group, 2- {4- [6-trifluoromethyl- (2-, 3) -, 4-, 5- or 7-) benzofurylmethyl]-(1-, 2- or 3-) piperazinyl}-(3-, 3-


4-, 5- or 6-) pyridyloxy group, 2- {4- [5-chloro- (2-, 3-, 4-, 6- or 7-) benzothienylmethyl]-(1-, 2- Or 3-) piperazinyl}-(3-, 4-, 5- or 6-) pyridyloxy group, 2- {4- [6-chloro- (2-, 3-, 4-, 5- or 7-) Benzofurylmethyl]-(1-, 2- or 3-) piperazinyl}-(3-, 4-, 5- or 6-) pyridyloxy group, 2- {4- [5-trifluoromethoxy- (2-) , 3-, 4-, 6- or 7-) benzofurylmethyl]-(1-, 2- or 3-) piperazinyl}-(3-, 4-, 5- or 6-) pyridyloxy group, 2- {4- [3- (4-Trifluoromethylphenyl) -2-propenyl]-(1-, 2- or 3-) piperazinyl} pyridyloxy , 2- {4- [3- (3,4-dichlorophenyl) -2-propenyl]-(1-, 2- or 3-) piperazinyl} pyridyloxy group, 2- {4- [3- (4-chlorophenyl) ) -2-propenyl]-(1-, 2- or 3-) piperazinyl} pyridyloxy group, 2- [4- {3- [6-trifluoromethyl- (2-, 3-, 4-, 5-) Or 7-) benzofuryl] -2-propenyl}-(1-, 2- or 3-) piperazinyl] pyridyloxy group, 2- [4- {3- [5-chloro- (2-, 3-, 4-] , 5- or 7-) benzofuryl] -2-propenyl}-(1-, 2- or 3-) piperazinyl] pyridyloxy group, 2- {4- [5-chloro- (2-, 3-, 4-) , 6- or 7-) benzofurylmethyl]-(1-, 2- or 3-) piperazinyl} (3-, 4-, 5- or 6-) pyridyloxy group, 2- {4- [2- (4-trifluoromethylphenyl)-(4- or 5-) thiazolylmethyl]-(1-, 2- Or 3-) piperazinyl} pyridyloxy group, 2- {4- [2- (4-trifluoromethoxyphenoxy) ethyl]-(1-, 2- or 3-) piperazinyl} pyridyloxy group, 2- {4- [3- (4-Trifluoromethoxyphenyl) -2-propenyl]-(1-, 2- or 3-) piperazinyl} pyridyloxy group, 2- {4- [5-trifluoromethoxy- (1-, 2 -, 3-, 4-, 6- or 7-) indolylmethyl]-(1-, 2- or 3-) piperazinyl} pyridyloxy group, 2- [4- (4-chlorophenoxymethyl)-(1 -, 2- or 3-) piperidyl]-(3 -, 4-, 5- or 6-) pyridyloxy group, 2- {4- [2- (4-chlorophenyl)-(3-, 4- or 5-) furylmethyl]-(1-, 2- or 3-) Piperazinyl} pyridyloxy group, 2- {4- [2- (2-chloro-5-trifluoromethylphenyl)-(3-, 4- or 5-) furylmethyl]-(1-, 2- Or a pyridyloxy group (such as a piperazyl group [a piperidine ring, a phenoxy group (a halogen atom, a halogen atom substituted or unsubstituted C 1 or substituted C 1 on a piperidine ring. 1 to 5, preferably 1 to 3 groups selected from the group consisting of 6 alkyl groups and halogen substituted or unsubstituted C1 to 6 alkoxy groups may be substituted), phenyl C1 to 6 alkoxy substituted C1 ~ 6 alkyl group ( One to five, preferably one, groups selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group on the nyl ring. Phenoxy C1-6 alkyl group in which the alkyl moiety is a linear or branched alkyl group having 1 to 6 carbon atoms (a halogen atom may be substituted or not substituted on the phenyl ring) 1-5, preferably 1 to 3 groups selected from the group consisting of a substituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group may be substituted) and phenyl C1 6 alkyl group (on the phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group 1 to 5, preferably 1 to 3 groups selected from the group consisting of at least one group selected from the group consisting of) and piperazinyl groups [piperazine On the ring, a C1-6 alkoxycarbonyl group, a furyl C1-6 alkyl group in which the alkyl moiety is a linear or branched alkyl group having 1 to 6 carbon atoms [1 to 3 on the furan ring Phenyl group (on the phenyl ring, a group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group is preferably 1 to 5) Is optionally substituted by 1 to 3)), a pyridyl C.sub.1-6 alkyl group in which the alkyl moiety is a linear or branched alkyl group having 1 to 6 carbon atoms [pyridine ring Above, the furyl and fe Group (on the phenyl ring, 1 to 5 groups selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group are preferred, And the group selected from the group consisting of 1 to 3 may be substituted by 1 to 3 groups], and the alkyl moiety is a linear or branched alkyl having 1 to 6 carbon atoms A benzothienyl C.sub.1-6 alkyl group which is a group (on the benzothiophene ring, selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group And the alkenyl moiety has a carbon number of 2 to 6 and a linear or branched alkenyl group having 1 to 3 double bonds, which is a trans-isomer and Wrap both sides of cis A phenyl C2-6 alkenyl group (on the phenyl ring, a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group 1 to 5, preferably 1 to 3), benzofuryl C1-6 alkyl group wherein the alkyl moiety is a linear or branched alkyl group having 1 to 6 carbon atoms [on a benzofuran ring Are optionally substituted one to three groups selected from the group consisting of halogen atoms, halogen substituted or unsubstituted C1-6 alkyl groups and halogen substituted or unsubstituted C1-6 alkoxy groups], alkenyl A linear or branched alkenyl group having a carbon number of 2 to 6 and 1 to 3 double bonds, and includes both trans and cis forms; [1 to 3 groups selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group are substituted on the benzoyl ring [benzofuran ring; Thiazolyl C.sub.1-6 alkyl group wherein the alkyl moiety is a linear or branched alkyl group having 1 to 6 carbon atoms [1 to 2 phenyl groups on the thiazole ring 1 to 5, preferably 1 to 3 groups selected from the group consisting of halogen atoms, halogen-substituted or unsubstituted C1-6 alkyl groups and halogen-substituted or unsubstituted C1-6 alkoxy groups (Optionally substituted), phenoxy C.sub.1-6 alkyl group in which the alkyl moiety is a linear or branched alkyl group having 1 to 6 carbon atoms (a halogen atom on the phenyl ring) , One to five, preferably one to three groups selected from the group consisting of a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted) An indolyl C.sub.1-6 alkyl group wherein the alkyl moiety is a linear or branched alkyl group having 1 to 6 carbon atoms (on the indole ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen) And a group selected from the group consisting of a substituted or unsubstituted C1-6 alkoxy group may be substituted with 1 to 3 groups, and a phenyl C1-6 alkyl group (on the phenyl ring, a benzofuryl group, a halogen atom, 1-5, preferably 1 to 3 groups selected from the group consisting of halogen-substituted or unsubstituted C1-6 alkyl groups and halogen-substituted or unsubstituted C1-6 alkoxy groups And selected from the group consisting of may also be) group can be exemplified groups may be 1-3 substituents selected from the group) consisting of may be in 1-3 substituents.

  1,2,3,4-tetrahydroquinolyloxy group (in the 1,2,3,4-tetrahydroquinoline ring, an oxo group, a phenyl group [on a phenyl ring, a halogen atom, a halogen substituted or unsubstituted At least one of a group selected from the group consisting of a C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group and a phenyl C1-6 alkyl group [on the phenyl ring , At least one of a group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group] As at least one kind of the selected group may be substituted), for example, 1,2,3,4-tetrahydro- (1-, 2-, 3-, 4-, 5) -, 6-, 7- or 8-) quinolyloxy group, 1- (4-trifluoromethylbenzyl) -2-oxo-1,2,3,4-tetrahydro-6-quinolyloxy group, 1- (4-triol) Fluoromethoxybenzyl) -2-oxo-1,2,3,4-tetrahydro-6-quinolyloxy group, 1- (4-chlorobenzyl) -2-oxo-1,2,3,4-tetrahydro-6-quinolyloxy Group, 1- (4-trifluoromethylbenzyl) -1,2,3,4-tetrahydro-6-quinolyloxy group, 1- (4-trifluoromethoxybenzyl) -1,2,3,4-tetrahydro-6 -Quinolyloxy group, 1- (4-chlorobenzyl) -1,2,3,4-tetrahydro-6-quinolyloxy group, 1- (4-chlorophenyl) -1,2,3,4-tetrahydro 6-quinolyloxy group, 1- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydro-6-quinolyloxy group, 1- (4-trifluoromethylphenyl) -1,2,3,4- Tetrahydro-6-quinolyloxy group, 1- (3,4-dichlorobenzyl) -1,2,3,4-tetrahydro-6-quinolyloxy group, 1- [3,4-di (trifluoromethoxy) benzyl] -1 1,2,3,4-tetrahydro-6-quinolyloxy group, 1- (4-chlorophenyl) -1,2,3,4-tetrahydro-5-quinolyloxy group, 1- (4-trifluoromethoxyphenyl) -1, 2,3,4-tetrahydro-5-quinolyloxy group, 1- (4-trifluoromethylphenyl) -1,2,3,4-tetrahydro-5-quinolyloxy group, -(4-chlorobenzyl) -1,2,3,4-tetrahydro-5-quinolyloxy group, 1- (4-trifluoromethoxybenzyl) -1,2,3,4-tetrahydro-5-quinolyloxy group, 1 -(4-Trifluoromethylbenzyl) -1,2,3,4-tetrahydro-5-quinolyloxy group, 1- [3,4,5-tri (trifluoromethyl) benzyl] -1,2,3,4 -Tetrahydro-6-quinolyloxy group, 1-benzyl-4-phenyl-1,2,3,4-tetrahydro-6-quinolyloxy group, 1-phenyl-4,6-dibenzyl-1,2,3,4-tetrahydro 1,2,3,4-Tetrahydroquinolyloxy group [1 such as -5-quinolyloxy group, 4-phenyl-2-oxo-1,2,3,4-tetrahydro-1-quinolyloxy group, etc. Oxo group, a phenyl group (a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 on the phenyl ring). Groups selected from the group consisting of alkoxy groups may be substituted by 1 to 5, preferably 1 to 3) and phenyl C1-6 alkyl groups (on the phenyl ring, halogen atoms, halogen substituted or not). 1-5, preferably 1-3, groups selected from the group consisting of substituted C1-6 alkyl groups and halogen substituted or unsubstituted C1-6 alkoxy groups may be substituted One to three selected groups may be substituted].

  Examples of the 1,2,3,4-tetrahydronaphthyloxy group (at least one oxo group may be substituted on the 1,2,3,4-tetrahydronaphthalene ring) include, for example, , 2-, 5- or 6-) 1,2,3,4-tetrahydronaphthyloxy group, 4-oxo-7-1,2,3,4-tetrahydronaphthyloxy group, 1,4-dioxo-6- 1,2,3,4-tetrahydronaphthyloxy groups such as 1,2,3,4-tetrahydronaphthyloxy group, 1,2,4-trioxo-5-1,2,3,4-tetrahydronaphthyloxy group 1 to 3 oxo groups may be substituted on the 1,2,3,4-tetrahydronaphthalene ring).

  Examples of the 2H-chromenoxyl group (wherein at least one oxo group may be substituted on the 2H-chromene ring) include 2H-chromenioxyl such as 2H-chromenioxyl group and 2-oxo-2H-chromenioxyl group. Mention may be made of the group (on the 2H-chromene ring, at least one oxo group may be substituted).

  Naphthyloxy group (on naphthalene ring, at least one piperidyl group [on piperidine ring, at least one phenoxy group (on phenyl ring, halogen atom, halogen-substituted or unsubstituted C1-6 alkyl group And at least one of a group selected from the group consisting of a halogen-substituted or unsubstituted C1-6 alkoxy group) may be substituted). For example, (1- or 2-) naphthyloxy group, 6- [4- (4-trifluoromethoxyphenoxy) -1-piperidyl] -2-naphthyloxy group, 5- (1-piperidyl) -2-naphthyl Oxy group, 2- (4-piperidyl) -3-naphthyloxy group, 4- (2-piperidyl) -1-naphthyloxy group, 5- (3-piperidyl) -2-naphthyloxy Group, 5,6-di (1-piperidyl) -1-naphthyloxy group, 7- (1-piperidyl) -6- [2- (2-fluorophenoxy) -1-piperidyl] -1-naphthyloxy group, 5,6,7-tri (1-piperidyl) -2-naphthyloxy group, 6- (4-phenoxy-1-piperidyl) -3-naphthyloxy group, 2- (2,4-diphenoxy-1-piperidyl) -4-naphthyloxy group, 3- (2,4,6-triphenoxy-1-piperidyl) -5-naphthyloxy group, 4- [2- (2-fluorophenoxy) -1-piperidyl] -6-naphthyl Oxy group, 4- [3- (3-fluorophenoxy) -2-piperidyl] -2-naphthyloxy group, 3- [4- (4-fluorophenoxy) -3-piperidyl] -1-naphthyloxy group, 5 -[2- 2-chlorophenoxy) -4-piperidyl] -2-naphthyloxy group, 6- [3- (3-chlorophenoxy) -5-piperidyl] -1-naphthyloxy group, 4- [4- (4-chlorophenoxy) group ) -2-piperidyl] -2-naphthyloxy group, 5- [5- (2-bromophenoxy) -2-piperidyl] -3-naphthyloxy group, 6- [6- (3-bromophenoxy) -3- Piperidyl] -4-naphthyloxy group, 6- [4- (4-bromophenoxy) -1-piperidyl] -2-naphthyloxy group, 3- [3- (2,3-dichlorophenoxy) -2-piperidyl] -4-naphthyloxy group, 6- [4- (3,4-dichlorophenoxy) -3-piperidyl] -1-naphthyloxy group, 4- [3- (2,4-dichlorophenoxy) -4-piperidyl] -2-naphthyloxy group, 5- [2- (3,4,5-trichlorophenoxy) -3-piperidyl] -2-naphthyloxy group, 6- [6- (2,4,6-trichlorophenoxy)- 2-piperidyl] -3-naphthyloxy group, 2- [3- (2,3,4,5,6-pentafluorophenoxy) -1-piperidyl] -3-naphthyloxy group, 4- [4- (2) -Methylphenoxy) -1-piperidyl] -2-naphthyloxy group, 3- [5- (3-methylphenoxy) -2-piperidyl] -2-naphthyloxy group, 5- [6- (4-methylphenoxy) group -3-piperidyl] -3-naphthyloxy group, 6- [1- (2-ethylphenoxy) -4-piperidyl] -4-naphthyloxy group, 2- [2- (3-ethylsiphenoxy) -1-] Piperidyl] -3-Na A thyloxy group, 3- [3- (4-ethylphenoxy) -2-piperidyl] -4-naphthyloxy group, 4- [4- (4-n-propylphenoxy) -3-piperidyl] -2-naphthyloxy group , 5- [5- (4-tert-Butylphenoxy) -4-piperidyl] -1-naphthyloxy group, 6- [2- (4-n-butylphenoxy) -3-piperidyl] -2-naphthyloxy group , 2- [1- (2-trifluoromethylphenoxy) -2-piperidyl] -4-naphthyloxy group, 3- [2- (3-trifluoromethylphenoxy) -1-piperidyl] -4-naphthyloxy group , 4- [3- (4-trifluoromethylphenoxy) -1-piperidyl] -2-naphthyloxy group, 5- [1- (2-pentafluoroethylphenoxy) -4-piperidine ] 3-Naphthyloxy group, 6- [1- (3-pentafluoroethyl phenoxy) -4-piperidyl] -2-naphthyloxy group, 2- [4- (2,3-dimethylphenoxy) -1-piperidyl] -1-naphthyloxy group, 3- [1- (3,4,5-trimethylphenoxy) -4-piperidyl] -2-naphthyloxy group, 4- [1- (4-n-pentylphenoxy) -4] -Piperidyl] -1-naphthyloxy group, 5- [4- (4-n-hexylphenoxy) -1-piperidyl] -2-naphthyloxy group, 6- [4- (2-methoxyphenoxy) -1-piperidyl ] 2-naphthyloxy group, 2- [1- (3-methoxyphenoxy) -4-piperidyl] -4-naphthyloxy group, 3- [1- (4-methoxyphenoxy) -4-piperidyl] -2- Naphthyloxy group, 4- [2- (2-ethoxyphenoxy) -3-piperidyl] -2-naphthyloxy group, 5- [3- (3-ethoxyphenoxy) -4-piperidyl] -1-naphthyloxy group, 6- [4- (4-ethoxyphenoxy) -5-piperidyl] -4-naphthyloxy group, 2- [3- (4-n-propoxyphenoxy) -2-piperidyl] -4-naphthyloxy group, 3- [2- (4-tert-butoxyphenoxy) -1-piperidyl] -4-naphthyloxy group, 4- [1- (4-n-butoxyphenoxy) -2-piperidyl] -2-naphthyloxy group, 5- [2- (2-Trifluoromethoxyphenoxy) -3-piperidyl] -2-naphthyloxy group, 6- [3- (3-trifluoromethoxyphenoxy) -4-piperidyl] -2 Naphthyloxy group, 6- [4- (4-trifluoromethoxyphenoxy) -3-piperidyl] -2-naphthyloxy group, 2- [3- (2-pentafluoroethoxyphenoxy) -2-piperidyl] -3- Naphthyloxy group, 3- [4- (4-pentafluoroethoxyphenoxy) -1-piperidyl] -2-naphthyloxy group, 4- [1- (2,3-dimethoxyphenoxy) -4-piperidyl] -2- Naphthyloxy group, 5- [4- (3,4,5-trimethoxyphenoxy) -1-piperidyl] -1-naphthyloxy group, 6- [4- (4-n-pentyloxyphenoxy) -1-piperidyl Naphthyloxy groups such as -3-naphthyloxy group, 5- [4- (4-n-hexyloxyphenoxy) -1-piperidyl] -1-naphthyloxy group, etc. 1 to 3 piperidyl groups on the thalene ring [1 to 3 phenoxy groups on the piperidine ring (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen 1 to 5, preferably 1 to 3 groups selected from the group consisting of substituted or unsubstituted C1-6 alkoxy groups may be substituted) Can be mentioned.

  1,2,3,4-tetrahydroisoquinolyloxy group (in the 1,2,3,4-tetrahydroisoquinoline ring, a C.sub.1-6 alkoxycarbonyl group, a phenyl C.sub.1-6 alkyl group [in the phenyl ring, And at least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted) [Wherein at least one of the selected groups may be substituted] and a phenyl group [in the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 At least one group selected from the group consisting of alkoxy groups may be substituted], at least one group selected from the group consisting of As, for example, 1,2,3,4-tetrahydroisoquinolyl (1-, 2-, 3-, 4-, 5-, 6-, 7- or 8-) quinolyloxy group , 2-tert-butoxycarbonyl-1,2,3,4-tetrahydro-6-isoquinolyloxy group, 2- (4-chlorobenzyl) -1,2,3,4-tetrahydro-6-isoquinolyl Oxy group, 2- (4-trifluoromethoxybenzyl) -1,2,3,4-tetrahydro-6-isoquinolyloxy group, 2- (4-trifluoromethylbenzyl) -1,2,3,4 -Tetrahydro-6-isoquinolyloxy group, 2-ethoxycarbonyl-4-benzyl-1,2,3,4-tetrahydro-7-isoquinolyloxy group, 1,4,6-tribenzyl-1,2,6 3,4-tetrahydro-8 Isoquinolyloxy group, 1- [3,4-di (trifluoromethoxy) benzyl] -1,2,3,4-tetrahydro-6-isoquinolyloxy group, 1- [3,4,5-triyl group (Trifluoromethyl) benzyl] -1,2,3,4-tetrahydro-6-isoquinolyloxy group, 2- (4-trifluoromethoxyphenyl)-(1-, 3-, 4-, 5-, 5-, A 1,2,3,4-tetrahydroisoquinolyloxy group such as a 6-, 7- or 8-) isoquinolyloxy group (on a 1,2,3,4-tetrahydroisoquinoline ring, C1-6 alkoxy A carbonyl group, a phenyl C1-6 alkyl group (on the phenyl ring, selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group Group may be substituted by 1 to 5, preferably 1 to 3) and the above phenyl group [in the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or not substituted; 1 to 5, preferably 1 to 3 groups selected from the group consisting of substituted C 1 to 6 alkoxy groups may be substituted], and 1 to 3 groups substituted from the group consisting of May be mentioned.

  Phenyl group [at least one piperidyl group on the phenyl ring (at least one phenoxy group on the piperidine ring [a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group on the phenyl ring, and At least one kind of group selected from the group consisting of halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted)) is substituted. ] As the 4- (1-piperidyl) phenyl group, 3- (2-piperidyl) phenyl group, 4- [4- (4-trifluoromethoxyphenoxy) -1-piperidyl] phenyl group, 4- [4- (1-piperidinyl) phenyl], for example 4- (4-trifluoromethylphenoxy) -1-piperidyl] phenyl group, 4- [4- (4-chlorophenoxy) -1-piperidyl] phenyl group, 4- {4- [3,4-di (tri) Fluoromethoxy) phenoxy-1-piperidyl]} phenyl group, 4- {4- (3,4,5-tri (trifluoromethyl) phenoxy-1-piperidyl)} phenyl group, 4- [4- (2,4) -Dichlorophenoxy) -1-piperidyl] phenyl group, 4- [4- (2,4,6-trifluorophenoxy) -1-piperidyl] phenyl group, 2- (2,4,5-triphenoxy) 1-piperidyl) phenyl group, 3- (1,2-diphenoxy-4-piperidyl) phenyl group, 2,4-di (4-piperidyl) phenyl group, 2,4,6-tri (3-piperidyl) phenyl group Etc. [1 to 3 piperidyl groups on the phenyl ring (1 to 3 phenoxy groups on the piperidine ring [a halogen atom on the phenyl ring, halogen substituted or unsubstituted C1 1 to 5, preferably 1 to 3 groups selected from the group consisting of 6 alkyl groups and halogen-substituted or unsubstituted C1-6 alkoxy groups may be substituted) Is assumed to be replaced. Can be mentioned.

Phenyl C 1-6 alkyl group [in the phenyl ring at least one piperidyl group (in the piperidine ring, in the phenoxy group [on the phenyl ring a halogen atom, halogen substituted or unsubstituted C 1-6 alkyl group and At least one of a group selected from the group consisting of halogen-substituted or unsubstituted C1-6 alkoxy group] may be substituted) and a group —NR ^{24 ′} R ^{25 ′} ( R ^{24 ′} represents a hydrogen atom or a C1-6 alkyl group R ^{25 ′} represents a phenyl C2-6 alkenyl group [on a phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen At least one group selected from the group consisting of a substituted or unsubstituted C.sub.1-6 alkoxy group may be substituted), and at least one group selected from the group consisting of For example, 4- (1-piperidyl) benzyl group, 2,4-di (4-piperidyl) benzyl group, 2,4,6-tri (2-piperidyl) benzyl group, 4- [4- (4-trifluoromethoxyphenoxy) -1-piperidyl] benzyl group, 4- [N-methyl-N- (4-trifluoromethoxycinnamyl) amino] benzyl group, 4- [N- (N- 4-trifluoromethoxycinnamyl) amino] benzyl group, 4- [4- (4-trifluoromethylphenoxy) -1-piperidyl] benzyl group, 4- [4- (4-chlorophenoxy) -1-piperidyl] Benzyl, 4- {4- [3,4-di (trifluoromethoxy) phenoxy] -1-piperidyl} benzyl, 4- {4- [2,4,6-tri (trifluoromethyl) phenyl Noxy] -1-piperidyl} benzyl group, 4- [4- (2,4-dichlorophenoxy) -1-piperidyl] benzyl group, 4- [4- (2,4,6-trifluorophenoxy) -1-] Piperidyl] benzyl, 3- [2,4-diphenoxy-3-piperidyl] benzyl, 2- [1,2,3-triphenoxy-4-piperidyl] benzyl, 4- [N-methyl-N- ( 4-trifluoromethoxycinnamyl) amino] -3- [4- (4-trifluoromethoxyphenoxy) -1-piperidyl] phenyl C1-6 alkyl group such as benzyl group [1 to 3 on phenyl ring (A phenoxy group on the piperidine ring [a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted group on the phenyl ring 1 to 5, preferably 1 to 3 groups selected from the group consisting of substituted C1-6 alkoxy groups may be substituted) and the group -NR ^{24 '} R ^25' (R ^{24 '} represents a hydrogen atom or a C1-6 alkyl group. R ^{25 ′} is a phenyl C2-6 alkenyl group [unsubstituted or halogen atom, halogen-substituted or unsubstituted C1-6 alkyl group and halogen-substituted or unsubstituted C1-6 alkoxy group selected from 1 to 5 groups , And preferably 1 to 3 substituted phenyl groups having 1 to 2 carbon atoms and an alkenyl group having 2 to 6 carbon atoms and 1 to 3 double bonds. And the group selected from the group consisting of 1 to 3 is substituted.

  Piperidyl C1-6 alkyl group (on the piperidine ring at least one phenyl group (on the phenyl ring a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 As the (4) phenyl group, for example, (4-phenyl-1-piperidyl) methyl group, 2) for example, it is preferable that at least one of the groups selected from the group consisting of alkoxy groups may be substituted). -(3-phenyl-2-piperidyl) ethyl group, 3- (2-phenyl-3-piperidyl) propyl group, 4- (1-phenyl-4-piperidyl) butyl group, 5- (4-phenyl-1-phenyl) Piperidyl) pentyl group, 6- (1-phenyl-2-piperidyl) hexyl group, 1- (4-trifluoromethoxyphenyl) -4-piperidyl methyl group, 1- (4-tributyl) Luomethylphenyl) -4-piperidyl methyl group, 1- (3-methoxyphenyl) -4-piperidyl methyl group, 1- (2-methylphenyl) -4-piperidyl methyl group, 1- (4-chlorophenyl)- 4-piperidyl methyl group, 1- [3,4-di (trifluoromethoxy) phenyl] -4-piperidyl methyl group, 1- [2,4,6-tri (trifluoromethyl) phenyl] -4-piperidyl methyl Group, 1- (3,4-dimethylphenyl) -4-piperidylmethyl group, 1- (2,4,6-trimethoxyphenyl) -4-piperidylmethyl group, 1- (3,4-dichlorophenyl) -4 -Piperidyl methyl group, 1- (2,4,6-tribromophenyl) -4-piperidyl methyl group, (1,2,6-triphenyl-4-piperidyl) methyl group, Piperidyl C1-6 alkyl groups such as (1,4-diphenyl-1-piperidyl) methyl group (1 to 3 phenyl groups on the piperidine ring (halogen atoms, halogen substituted or unsubstituted C1 on the phenyl ring 1 to 5, preferably 1 to 3 groups selected from the group consisting of an alkyl group of 6 to 6 and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted) Can be mentioned.

  Phenyl C1-6 alkyl group [wherein at least one phenyl group (a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 on the phenyl ring Examples of the group in which at least one group selected from the group consisting of alkoxy groups is substituted) are, for example, 2- (2-fluorophenyl) benzyl group, 3- (3-fluorophenyl) benzyl group, 4- (4-fluorophenyl) benzyl group, 2- (2-chlorophenyl) benzyl group, 3- (3-chlorophenyl) benzyl group, 4- (4-chlorophenyl) benzyl group, 2- (2-bromophenyl) benzyl group, 3- (3-bromophenyl) benzyl group, 4- (4-bromophenyl) benzyl group, 2- (2-bromophenyl) benzyl group 2-iodophenyl) benzyl group, 3- (3-iodophenyl) benzyl group, 4- (4-iodophenyl) benzyl group, 4- (2,3-difluorophenyl) benzyl group, 3- (3,4-) Difluorophenyl) benzyl group, 2- (3,5-difluorophenyl) benzyl group, 4- (2,4-difluorophenyl) benzyl group, 3- (2,6-difluorophenyl) benzyl group, 2- (2, 3-dichlorophenyl) benzyl group, 4- (3,4-dichlorophenyl) benzyl group, 3- (3,5-dichlorophenyl) benzyl group, 2- (2,4-dichlorophenyl) benzyl group, 4- (2, 6- Dichlorophenyl) benzyl group, 3- (2-fluoro-4-bromophenyl) benzyl group, 2- (4-chloro-3-fluorophenyl) benzyl group, 4 (2,3,4-Trichlorophenyl) benzyl, 3- (3,4,5-trifluorophenyl) benzyl, 2- (2,4,6-trichlorophenyl) benzyl, 4- (4-isopropyl) Phenyl) benzyl group, 3- (4-n-butylphenyl) benzyl group, 2- (4-methylphenyl) benzyl group, 4- (2-methylphenyl) benzyl group, 3- (3-methylphenyl) benzyl group , 2- (2,4-dimethylphenyl) benzyl group, 4- (2,3-dimethylphenyl) benzyl group, 3- (2,6-dimethylphenyl) benzyl group, 2- (3,5-dimethylphenyl) Benzyl group, 4- (2,5-dimethylphenyl) benzyl group, 3- (2,4,6-trimethylphenyl) benzyl group, 2- (3,5-ditrifluoromethylphenyl) ben Dyl group, 4- (2,3,4,5,6-pentafluorophenyl) benzyl group, 3- (4-isopropoxyphenyl) benzyl group, 2- (4-n-butoxyphenyl) benzyl group, 4- (4-methoxyphenyl) benzyl group, 3- (2-methoxyphenyl) benzyl group, 2- (3-methoxyphenyl) benzyl group, 4- (2,4-dimethoxyphenyl) benzyl group, 3- (2,3 -Dimethoxyphenyl) benzyl group, 2- (2,6-dimethoxyphenyl) benzyl group, 2- (3,5-dimethoxyphenyl) benzyl group, 4- (2,5-dimethoxyphenyl) benzyl group, 3- (2) 4,6-trimethoxyphenyl) benzyl group, 2- (3,5-ditrifluoromethoxyphenyl) benzyl group, 4- (2-isopropoxyphenyl) benzyl group, -(3-chloro-4-methoxyphenyl) benzyl group, 2- (2-chloro-4-trifluoromethoxyphenyl) benzyl group, 4- (3-methyl-4-fluorophenyl) benzyl group, 3- (4 -Bromo-3-trifluoromethylphenyl) benzyl group, 4- (2-trifluoromethylphenyl) benzyl group, 3- (3-trifluoromethylphenyl) benzyl group, 4- (4-trifluoromethylphenyl) benzyl Group, 2- (2-pentafluoroethylphenyl) benzyl group, 3- (3-pentafluoroethylphenyl) benzyl group, 2- (4-pentafluoroethylphenyl) benzyl group, 4- (2-trifluoromethoxyphenyl) ) Benzyl group, 3- (3-trifluoromethoxyphenyl) benzyl group, 4- (4-trifluorometh) Siphenyl) benzyl group, 4- (2-pentafluoroethoxyphenyl) benzyl group, 3- (3-pentafluoroethoxyphenyl) benzyl group, 2- (4-pentafluoroethoxyphenyl) benzyl group, 2- [4- (4- 2-trifluoromethylphenyl) phenyl] ethyl group, 2- [3- (3-trifluoromethylphenyl) phenyl] ethyl group, 2- [2- (4-trifluoromethylphenyl) phenyl] ethyl group, 2- [4- (2-Trifluoromethoxyphenyl) phenyl] ethyl group, 2- [3- (3-trifluoromethoxyphenyl) phenyl] ethyl group, 2- [2- (4-trifluoromethoxyphenyl) phenyl] ethyl Group, 2- [4- (2-pentafluoroethoxyphenyl) phenyl] ethyl group, 2- [3- (3-pentafluoroethoxyphenyl) group -Yl) phenyl] ethyl group, 2- [2- (4-pentafluoroethoxyphenyl) phenyl] ethyl group, 3- [4- (2-trifluoromethylphenyl) phenyl] propyl group, 3- [3- (3) -Trifluoromethylphenyl) phenyl] propyl group, 3- [2- (4-trifluoromethylphenyl) phenyl] propyl group, 3- [4- (2-trifluoromethoxyphenyl) phenyl] propyl group, 3- [4 3- (3-trifluoromethoxyphenyl) phenyl group, 3- [2- (4-trifluoromethoxyphenyl) phenyl] propyl group, 3- [4- (3-pentafluoroethoxyphenyl) phenyl] propyl group , 3- [3- (4-pentafluoroethoxyphenyl) phenyl] propyl group, 4- [2- (3-pentafluoroethoxyphenyl) phenyl] Ethyl group, 5- [4- (4-trifluoromethylphenyl) phenyl] pentyl group, 4- [3- (4-trifluoromethylphenyl) phenyl] pentyl group, 4- [2- (4-trifluoromethoxy) Phenyl) phenyl] pentyl group, 6- [4- (3-trifluoromethylphenyl) phenyl] hexyl group, 6- [3- (4-trifluoromethylphenyl) phenyl] hexyl group, 6- [2- (4) -Alkyl moiety such as trifluoromethoxyphenyl) phenyl] hexyl group, 2,4-di (4-trifluoromethylphenyl) benzyl group and 2,4,6-tri (4-trifluoromethoxyphenyl) benzyl group is carbon A phenylalkyl group which is a linear or branched alkyl group having 1 to 6 [1 to 3 phenyl groups on the phenyl ring (a halogen source on the phenyl ring Or a group selected from the group consisting of halogen-substituted or unsubstituted linear or branched C1-6 alkyl groups and halogen-substituted or unsubstituted linear or branched C1-6 alkoxy groups; To which 5 to 5 and preferably 1 to 3 are substituted) can be mentioned.

  Piperazinyl C1-6 alkyl group (in the piperazine ring, at least one phenyl group [in the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 Examples of the group in which at least one group selected from the group consisting of an alkoxy group may be substituted] may be substituted, for example, 1-piperazinylmethyl group, 1- (2-piperazinyl) Ethyl group, 2- (1-piperazinyl) ethyl group, 3- (1-piperazinyl) propyl group, 2- (1-piperazinyl) propyl group, 4- (2-piperazinyl) butyl group, 5- (2-piperazinyl) group Pentyl group, 4- (1-piperazinyl) pentyl group, 6- (1-piperazinyl) hexyl group, 2-methyl-3- (1-piperazinyl) propyl group, 1,1 Dimethyl-2- (1-piperazinyl) ethyl group, (4-phenyl-1-piperazinyl) methyl group, (2,4-diphenyl-1-piperazinyl) methyl group, (2,4,5-triphenyl-1-methyl group) Piperazinyl) methyl group, [4- (4-trifluoromethoxyphenyl) -1-piperazinyl] methyl group, [4- (4-trifluoromethylphenyl) -1-piperazinyl] methyl group, [4- (4-chlorophenyl) methyl group ) -1-Piperazinyl] methyl group, [4- (2,4-dichlorophenyl) -1-piperazinyl] methyl group, [4- (2,4,6-trifluorophenyl) -1-piperazinyl] methyl group, 2,4-di (trifluoromethyl) phenyl-1-piperazinyl] methyl group, [2,4,6-tri (trifluoromethoxy) phenyl-1-pipera Piperazinyl C.sub.1-6 alkyl groups (such as 1 to 3 phenyl groups on the piperazine ring [a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted on the piperazine ring. Or 1 to 5, preferably 1 to 3 groups selected from the group consisting of unsubstituted C1-6 alkoxy groups may be substituted).

  Piperidyl C1-6 alkyl group (in the piperidine ring, at least one phenoxy group [in the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 Examples of a group in which at least one group selected from the group consisting of an alkoxy group may be substituted] may be substituted, for example, 1-piperidylmethyl group, 2- (2-piperidyl) ethyl group 3- (3-piperidyl) propyl group, 4- (4-piperidyl) butyl group, 5- (1-piperidyl) pentyl group, 6- (2-piperidyl) hexyl group, 1- (4-trifluoromethoxyphenoxy) ) -4-piperidylmethyl group, 1- (4-trifluoromethylphenoxy) -4-piperidylmethyl group, 2-methyl-3- (piperidin-1-yl) Propyl group, 1,1-dimethyl-2- (piperidin-1-yl) ethyl group, 1- (4-chlorophenoxy) -4-piperidyl methyl group, 1- [3,4-di (trifluoromethoxy) phenoxy ]-4-piperidyl methyl group, 1- [2,4,6- tri (trifluoro methoxy) phenoxy] 4-piperidyl methyl group, 1-(3, 4- dichloro phenoxy) 4-piperidyl methyl group, 1 -(2,4,6-tribromophenoxy) -4-piperidylmethyl group, (1,2,6-triphenoxy-4-piperidyl) methyl group, (2,4-diphenoxy-1-piperidyl) methyl group and the like Piperidyl C1-6 alkyl group (1 to 3 phenoxy groups on the piperidine ring [halogen atoms on the phenyl ring, halogen substituted or unsubstituted C1-6 alkyl And 1 to 5, preferably 1 to 3 groups selected from the group consisting of halogen-substituted or unsubstituted C1-6 alkoxy groups may be substituted). It can be mentioned.

  A thiazolyl group [on a thiazole ring, a phenyl group (on a phenyl ring, selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group; At least one of the above groups may be substituted), piperazinyl C.sub.1-6 alkyl group (on the piperazine ring, at least one phenyl group [on the phenyl ring, a halogen atom, halogen substituted or unsubstituted At least one of a group selected from the group consisting of a C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted) and piperidyl C1-6 An alkyl group (on the piperidine ring at least one phenoxy group [on the phenyl ring a halogen atom, halogen substituted or unsubstituted C 1 to 6 A group selected from the group consisting of an alkyl group and a group selected from the group consisting of halogen-substituted or unsubstituted C1-6 alkoxy groups] optionally substituted) As at least one of which may be substituted], for example, (2-, 4- or 5-) thiazolyl group, 2- (4-trifluoromethoxyphenyl) -5-thiazolyl group, 2- [4 -(4-Trifluoromethoxyphenyl) -1-piperazinyl] methyl-5-thiazolyl group, 2- [4- (4-trifluoromethoxyphenoxy) -1-piperidyl] methyl-5-thiazolyl group, 2- [2 , 4-Di (trifluoromethoxy) phenyl] -5-thiazolyl group, 2- {4- [2,4-di (trifluoromethoxy) phenyl] -1-piperazinyl} methyl-5-thiazo Group, 2- {4- [2,4-di (trifluoromethoxy) phenoxy] -1-piperidyl} methyl-5-thiazolyl group, 2- (4-trifluoromethylphenyl) -5-thiazolyl group, 2 -[4- (4-trifluoromethylphenyl) -1-piperazinyl] methyl-5-thiazolyl group, 2- [4- (4-trifluorotylphenoxy) -1-piperidyl] methyl-5-thiazolyl group, 2 -[2,4,6-tri (trifluoromethyl) phenyl] -5-thiazolyl group, 2- {4- [2,4,6-tri (trifluoromethyl) phenyl] -1-piperazinyl} methyl-5 -Thiazolyl group, 2- {4- [2,4,6-tri (trifluoromethyl) phenoxy] -1-piperidyl} methyl-5-thiazolyl group, 2- (4-chlorophenyl) -5-thia Zoryl group, 2- [4- (4-chlorophenyl) -1-piperazinyl] methyl-5-thiazolyl group, 2- [4- (2-chlorophenoxy) -1-piperidyl] methyl-5-thiazolyl group, 2- (2,4-dichlorophenyl) -5-thiazolyl group, 2- [4- (2,4-dichlorophenyl) -1-piperazinyl] methyl-5-thiazolyl group, 2- [4- (2,4-dichlorophenoxy) group -1-piperidyl] methyl-5-thiazolyl group, 2- (2,4,6-trifluorophenyl) -5-thiazolyl group, 2- [4- (2,4,6-trifluorophenyl) -1-] Piperazinyl] methyl-5-thiazolyl group, 2- [4- (2,4,6-trifluorophenoxy) -1-piperidyl] methyl-5-thiazolyl group, 2- (2,4-diphenoxy-1-pipe) Dyl) methyl-5-thiazolyl group, 5- (2,4,5-triphenoxy-1-piperidyl) methyl-2-thiazolyl group, 5- (2,4-diphenyl-1-piperazinyl) methyl-2-thiazolyl Group, a thiazolyl group such as 2- (2,4,5-triphenyl-1-piperazinyl) methyl-4-thiazolyl group, 4- (1-piperidyl) -2- (1-piperazinyl) -5-thiazolyl group, etc. On the thiazole ring, a phenyl group (on the phenyl ring, a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group is 1 to 5, preferably 1 to 3 substituted, piperazinyl C1-6 alkyl group (1 to 3 phenyl groups on the piperazine ring [halo on the phenyl ring 1 to 5, preferably 1 to 3 groups selected from the group consisting of halogen atoms, halogen substituted or unsubstituted C1-6 alkyl groups and halogen substituted or unsubstituted C1-6 alkoxy groups (May be substituted) and piperidyl C1-6 alkyl group (one to three phenoxy groups on the piperidine ring [on the phenyl ring, halogen atoms, halogen substituted or unsubstituted C1 1 to 5, preferably 1 to 3 groups selected from the group consisting of 6 alkyl groups and halogen-substituted or unsubstituted C1-6 alkoxy groups may be substituted) And one or two groups selected from the group consisting of

  A benzoxazolyloxy group (on a benzoxazole ring, a piperazinyl group [on a piperazine ring, a phenyl C.sub.1-6 alkyl group (on a phenyl ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group And at least one of a group selected from the group consisting of halogen substituted or unsubstituted C1-6 alkoxy group may be substituted) and phenyl C2-6 alkenyl group (on the phenyl ring, a halogen atom, halogen A group selected from the group consisting of a substituted or unsubstituted C1-6 alkyl group and a group selected from the group consisting of a halogen-substituted or unsubstituted C1-6 alkoxy group; At least one of the above may be substituted], piperidyl group [on the piperidine ring, a phenyl C.sub.1-6 alkyl group (phenyl At least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted on the above) And an amino group (on the amino group, a C1-6 alkyl group and a phenyl group [on a phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy At least one group selected from the group consisting of groups may be substituted] at least one group selected from the group consisting of at least one group selected from the group consisting of And a phenyl group (on the phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1-6 group. As at least one kind of the groups selected from the group consisting of the group consisting of the group consisting of the alkoxy group and the at least one kind of the group selected from the group consisting of the alkoxy group may be substituted), for example, 2 -[4- (4-trifluoromethoxybenzyl) -1-piperazinyl] -6-benzoxazolyloxy group, 2-phenyl-5-benzoxazolyloxy group, 2- (4-chlorophenyl) -5- Benzoxazolyloxy group, 2- [4- (4-trifluoromethylbenzyl) -1-piperazinyl] -6-benzoxazolyloxy group, 2- [4- (4-chlorobenzyl) -1-piperazinyl 6-benzoxazolyloxy group, 2- {4- [2,4,6-tri (trifluoromethoxy) benzyl] -1-piperazinyl} -6-benzoxazolyloxy group, 2 -{4- [2,4-di (trifluoromethyl) benzyl] -1-piperazinyl} -6-benzoxazolyloxy group, 2- [4- (2,4-dichlorobenzyl) -1-piperazinyl] -6-benzoxazolyloxy group, 2- [4- (2,4,6-trifluorobenzyl) -1-piperazinyl] -6-benzoxazolyloxy group, 2- (4-benzyl-1-yl) Piperazinyl) -4-benzoxazolyloxy group, 2- (2,4-dibenzyl-1-piperazinyl) -7-benzoxazolyloxy group, 2- (2,4,6-tribenzyl-1-piperazinyl) -6-benzoxazolyloxy group, 2- (4-trifluoromethoxyphenyl) -5-benzoxazolyloxy group, 2- (4-trifluoromethylphenyl) -5-benzoxazole Oxy group, 2- (2,4-dibromophenyl) -5-benzoxazolyloxy group, 2- (2,4,6-trichlorophenyl) -5-benzoxazolyloxy group, 2- [2, 2, 4,6-Tri (trifluoromethoxy) phenyl] -5-benzoxazolyloxy group, 2- [2,4-di (trifluoromethyl) phenyl] -5-benzoxazolyloxy group, 4-phenyl -5- (1-piperazinyl) -2-benzoxazolyloxy group, 2,4,5-triphenyl-7-benzoxazolyloxy group, 2- [4- (4-trifluoromethoxybenzyl) )-(1-, 2- or 3-) piperidyl]-(2-, 4-, 5-, 6- or 7-) benzoxazolyloxy group, 2- {4- [3- (4-tri) Fluoromethylphenyl) -2-propenyl] (1-, 2- or 3-) piperazinyl}-(2-, 4-, 5-, 6- or 7-benzoxazolyloxy group, 4- [N-methyl-N- (4-chlorophenyl) amino ]-(1-, 2- or 3-) piperidyl]-(2-, 4-, 5-, 6- or 7-) benzoxazolyloxy group such as benzoxazolyloxy group (on benzoxazole ring The piperazinyl group [in the piperazine ring, a phenyl C.sub.1-6 alkyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy. Groups selected from the group consisting of 1 to 5 groups, preferably 1 to 3 groups) and the alkenyl moiety has 2 to 6 carbon atoms and a linear chain having 1 to 3 double bonds Or branched alkenyl groups and Phenyl C2-6 alkenyl group (including a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy on the phenyl ring Group selected from the group consisting of 1 to 5 groups, preferably 1 to 3 groups may be substituted), and 1 to 3 groups selected from the group consisting of groups may be substituted], piperidyl Group [on the piperidine ring, a phenyl C.sub.1-6 alkyl group (on the phenyl ring, a group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group Groups selected from 1 to 5 and preferably 1 to 3) and an amino group (on the amino group, a C1 to 6 alkyl group and a phenyl group [on the phenyl ring 1-5, preferably 1-3, are selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group And one to two groups selected from the group selected from the group consisting of) may be substituted one to three) and a phenyl group (on the phenyl ring) Is substituted by 1 to 5, preferably 1 to 3 groups selected from the group consisting of halogen atoms, halogen-substituted or unsubstituted C.sub.1-6 alkyl groups and halogen-substituted or unsubstituted C.sub.1-6 alkoxy groups; And one to three groups selected from the group consisting of Can be mentioned.

  A benzimidazolyloxy group (on the benzimidazole ring, a C1-6 alkyl group, a phenyl group on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 At least one group selected from the group consisting of alkoxy groups may be substituted, piperidyl group [at least one phenoxy group on a piperidine ring (a halogen atom on a phenyl ring, halogen substitution or At least one of a group selected from the group consisting of an unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted), piperazinyl Group [in the piperazine ring, at least one phenyl C.sub.1-6 alkyl group (on the phenyl ring, a halogen atom, halogen Or at least one of a group selected from the group consisting of an unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted) and Phenyl C1-6 alkyl group [in which at least one of the groups selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group on a phenyl ring As the (optionally substituted) species, at least one group selected from the group consisting of may be substituted), for example (1-, 2-, 4-, 5-, 6- or 7-) benzoimidazolyloxy group, 2-phenyl-5-benzoimidazolyloxy group, 1-methyl-5-benzoimidazolyloxy group, 1-methyl-2-phenyl-5-benzoimidazolyl Xy group, 2- (4-chlorophenyl) -5-benzoimidazolyloxy group, 1-methyl-2- (4-chlorophenyl) -5-benzoimidazolyloxy group, 1,2-diphenyl-5-benzoimidazolyloxy group, 1, 4 -Dimethyl-5-benzoimidazolyloxy group, 1-methyl-2, 6-diphenyl-5-benzoimidazolyloxy group, 2- (4-trifluoromethylphenyl) -5-benzoimidazolyloxy group, 1-methyl-2- (4) -Trifluoromethoxyphenyl) -5-benzoimidazolyloxy group, 1,2,7-triphenyl-5-benzoimidazolyloxy group, 1,2,4-trimethyl-5-benzoimidazolyloxy group, 1-ethyl-2, 6- Diphenyl-5-benzoimidazolyloxy group, 2- [2,4-di (triflic) Luomethyl) phenyl] -5-benzoimidazolyloxy group, 1-methyl-2- [2,4,6-tri (trifluoromethoxy) phenyl] -5-benzoimidazolyloxy group, 2- (2,4-dichlorophenyl) -5 -Benzoimidazolyloxy group, 2- (2,4,6-trifluorophenyl) -5-benzoimidazolyloxy group, 2- (3-bromophenyl) -5-benzoimidazolyloxy group, 2- (2-iodophenyl) -5 -Benzoimidazolyloxy group, 2- [4-trifluoromethoxyphenoxy- (1-, 2- or 3-) piperidyl]-(1-, 4-, 5-, 6- or 7-) imidazolyloxy group, 1- Benzyl-2- [4-trifluoromethoxybenzyl- (1-, 2- or 3-) piperazinyl]-(4-, 5-, 6- or 7-) Benzimidazolyloxy groups (such as benzimidazole rings such as 1- (4-trifluoromethoxybenzyl)-(2-, 4-, 5-, 6- or 7-) imidazolyloxy group, and the like; [C1-6 alkyl group, phenyl group [on the phenyl ring, a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group] 1 to 5, preferably 1 to 3 substituted, piperidyl group [1 to 3 phenoxy groups on the piperidine ring (halogen atoms on the phenyl ring, halogen substituted or unsubstituted One to five, preferably one to three, groups selected from the group consisting of a C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group may be substituted May be substituted], piperazinyl group [1 to 3 phenyl C1-6 alkyl groups on the piperazine ring (on the phenyl ring, halogen atoms, halogen substituted or unsubstituted C1-6 alkyl groups And 1 to 5, preferably 1 to 3 groups selected from the group consisting of halogen-substituted or unsubstituted C1-6 alkoxy groups may be substituted) and phenyl C1 To 6 alkyl groups [in the phenyl ring, 1 to 5 groups selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group , And preferably 1 to 3 groups may be substituted], and groups selected from the group consisting of 1 to 3 may be substituted).

  1,2,3,4-tetrahydroisoquinolyl group (on the 1,2,3,4-tetrahydroisoquinoline ring, an (m-1) amino group [on an amino group a C1 to 6 alkyl group, phenyl Group (on the phenyl ring, at least one of a group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group is substituted) And phenyl C1-6 alkyl group (on the phenyl ring, selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group And at least one group selected from the group consisting of at least one group may be substituted) and (m-2) phenoxy group [on the phenyl ring, halogen original At least one group selected from the group consisting of a group consisting of a halogen, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group] As at least one of the substituted groups, one may substitute, for example, (1-, 2-, 3-, 4-, 5-, 6-, 7- or 8-) 1, 2, 3 , 4-tetrahydroisoquinolyl group, 7- [N-methyl-N- (4-trifluoromethoxyphenyl) amino] -1,2,3,4-tetrahydro-2-isoquinolyl group, 7- [N-methyl -N- (4-trifluoromethoxybenzyl) amino] -1,2,3,4-tetrahydro-2-isoquinolyl group, 6- (4-trifluoromethoxyphenoxy) -1,2,3,4-tetrahydro- 2-isoquinolyl 7- [N-Methyl-N- (4-trifluoromethylphenyl) amino] -1,2,3,4-tetrahydro-2-isoquinolyl, 7- [N-methyl-N- (4-trifluoro) [Methylbenzyl) amino] -1,2,3,4-tetrahydro-2-isoquinolyl group, 6- (4-trifluoromethylphenoxy) -1,2,3,4-tetrahydro-2-isoquinolyl group, 7- [ N-methyl-N- (4-chlorophenyl) amino] -1,2,3,4-tetrahydro-2-isoquinolyl group, 7- [N- (4-chlorophenyl) amino] -1,2,3,4- Tetrahydro-2-isoquinolyl group, 7- [N-methyl-N- (4-chlorobenzyl) amino] -1,2,3,4-tetrahydro-2-isoquinolyl group, 7- [N- (4-chlorobenzyl) )amino -1,2,3,4-tetrahydro-2-isoquinolyl group, 6- (4-chlorophenoxy) -1,2,3,4-tetrahydro-2-isoquinolyl group, 7- {N-methyl-N- [2,4-Di (trifluoromethoxy) phenyl] amino} -1,2,3,4-tetrahydro-2-isoquinolyl group, 7- {N-methyl-N- [2,4,6-tri (tri) Fluoromethoxy) benzyl] amino} -1,2,3,4-tetrahydro-2-isoquinolyl group, 6- [2,4-di (trifluoromethoxy) phenoxy] -1,2,3,4-tetrahydro-2 -Isoquinolyl group, 7- {N-methyl-N- [2,4,6-tri (trifluoromethyl) phenyl] amino} -1,2,3,4-tetrahydro-2-isoquinolyl group, 7- {N -Methyl-N- [2,4-di (Trifluoromethyl) benzyl] amino} -1,2,3,4-tetrahydro-2-isoquinolyl group, 6- [2,4,6-tri (trifluoromethyl) phenoxy] -1,2,3,4 -Tetrahydro-2-isoquinolyl group, 7- [N-methyl-N- (2,4-dibromophenyl) amino] -1,2,3,4-tetrahydro-2-isoquinolyl group, 7- [N-methyl- N- (2,3-diiodobenzyl) amino] -1,2,3,4-tetrahydro-2-isoquinolyl group, 6- (2,4,6-trifluorophenoxy) -1,2,3,4 -Tetrahydro-2-isoquinolyl group, 7-amino-6-phenoxy-1,2,3,4-tetrahydro-2-isoquinolyl group, 4,5,6-triphenoxy-1,2,3,4-tetrahydro- 7-isoquinolyl Etc. (1,2,3,4-tetrahydroisoquinolyl group (1,2,3,4-tetrahydroisoquinoline ring, amino group [amino group, C1-6 alkyl group, phenyl group (phenyl There are 1 to 5 groups, preferably 1 to 3 groups selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group on the ring. And optionally substituted phenyl and phenyl C1-6 alkyl (on the phenyl ring, consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl and a halogen substituted or unsubstituted C1-6 alkoxy) And one to two groups selected from the group consisting of 1 to 5 groups, and preferably 1 to 3 groups may be substituted) and the phenoxy described above Group One to five, preferably one, groups selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group on the nyl ring. 1 to 3 of the groups selected from the group consisting of 3) may be substituted.

  C1-6 alkoxy group substituted with two phenyl groups [wherein a phenyl ring is selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group As at least one kind of the substituted groups] may be, for example, 1,1-diphenylmethoxy, 1,2-diphenylethoxy, 3,3-diphenylpropoxy, 3,4-diphenylbutoxy Group, 3,5-diphenylpentyloxy group, 4,6-diphenylhexyloxy group, 1,1-di (4-trifluoromethoxyphenyl) methoxy group, 1- (2-fluorophenyl) -1- (3-) Fluorophenyl) methoxy group, 1- (4-fluorophenyl) -1- (2-chlorophenyl) methoxy group, 1- (3-chlorophenyl) methoxy group L)-(4-chlorophenyl) methoxy group, 1- (2-bromophenyl) -1- (3-bromophenyl) methoxy group, 1- (4-bromophenyl) -2- (2-iodophenyl) Ethoxy group, 3- (3-iodophenyl) -3- (4-iodophenyl) propoxy group, 1- (2,3-difluorophenyl) -1- (3,4-difluorophenyl) methoxy group, 4- (4- 3,5-Difluorophenyl) -4- (2,4-difluorophenyl) butoxy, 5- (2,6-difluorophenyl) -5- (2,3-dichlorophenyl) pentyloxy, 6- (3, 4-dichlorophenyl) -6- (3,5-dichlorophenyl) hexyloxy group, 1- (2,4-dichlorophenyl) -1- (2,6-dichlorophenyl) methoxy group, 1- (3) 4,5-Trifluorophenyl) -1- (3,4,5-trichlorophenyl) methoxy group, 1- (2,3,4,5,6-pentafluorophenyl) -1- (2,4,6 -Trimethylphenyl) methoxy group, 1- (4-n-butylphenyl) -1- (2,4-dimethylphenyl) methoxy group, 1- (3,5-ditrifluoromethylphenyl) -1- (4-n) -Butoxyphenyl) methoxy group, 1- (2,4-dimethoxyphenyl) -1- (2,3-dimethoxyphenyl) methoxy group, 1- (2,4,6-trimethoxyphenyl) -1- (3, 5-ditrifluoromethoxyphenyl) methoxy group, 1- (3-chloro-4-methoxyphenyl) -1- (2-chloro-4-trifluoromethoxyphenyl) methoxy group, 1- (3-methyl-4-fluoro Rophenyl) -1- (4-bromo-3-trifluoromethylphenyl) methoxy, 1- (2-methylphenyl) -1- (3-methylphenyl) methoxy, 1- (2-pentafluoroethylphenyl) -1- (3-Pentafluoroethylphenyl) methoxy, 1- (2-isopropylphenyl) -1- (2-tert-butylphenyl) methoxy, 1- (2-sec-butylphenyl) -1- ( 2-n-heptafluoropropylphenyl) methoxy group, 1- (4-pentylphenyl) -1- (4-hexylphenyl) methoxy group, 1- (2-methoxyphenyl) -1- (2,6-dimethoxyphenyl) ) Methoxy group, 1- (2-pentafluoroethoxyphenyl) -1- (isopropoxyphenyl) methoxy group, 1- (2-tert-butyl) Xyphenyl) -1- (2-sec-butoxyphenyl) methoxy group, 1- (2-n-heptafluoropropoxyphenyl) -1- (4-n-pentoxyphenyl) methoxy group, 1,1-di (4) A C1-6 alkoxy group substituted by two phenyl groups such as -n-hexyloxyphenyl) methoxy group (a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted on a phenyl ring 1 to 5, preferably 1 to 3 groups selected from the group consisting of C1-6 alkoxy groups of the above) may be mentioned.

  Phenyl C1-6 alkyl group [in the phenyl ring (at least one phenyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1 6) at least one of a group selected from the group consisting of alkoxy groups may be substituted), for example, 4-phenylbenzyl group, 3-phenylbenzyl group, 2 -Phenylbenzyl group, 2,4-diphenylbenzyl group, 2,4,6-triphenylbenzyl group, 4- (4-trifluoromethoxyphenyl) benzyl group, 2- (3-trifluoromethylphenyl) benzyl group, 4- (2-fluorophenyl) benzyl group, 3- (4-chlorophenyl) benzyl group, 4- (4-methoxyphenyl) benzyl group, 3- 4-methylphenyl) benzyl group, 2- (3,4-dimethoxyphenyl) benzyl group, 4- (3,4-dimethylphenyl) benzyl group, 3- (3,4,6-trimethoxyphenyl) benzyl group, 2- (2,4,5-trimethylphenyl) benzyl group, 4- (3,4-dichlorophenyl) benzyl group, 2- (2,4,6-trifluorophenyl) benzyl group, 4- (3-chloro-) 4-trifluoromethoxyphenyl) benzyl group, 2- [4- (2-fluorophenyl) phenyl] ethyl group, 3- [2- (3,4-dimethoxyphenyl) phenyl] propyl group, 4- [2- (2- (4- (2-fluorophenyl) phenyl)] 2,4,5-trimethylphenyl) phenyl] butyl group, 5- [4- (3-chloro-4-trifluoromethoxyphenyl) phenyl] pentyl group, 6- [2- (3-tri) Phenyl in which the alkyl moiety such as trifluoromethylphenyl) phenyl] hexyl group or 1- [4- (4-trifluoromethoxyphenyl) phenyl] ethyl group is a linear or branched alkyl group having 1 to 6 carbon atoms C1-6 alkyl group [in the phenyl ring (1 to 3 phenyl groups (in the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1 And the group selected from the group consisting of 6 alkoxy groups may be substituted by 1 to 5, and preferably 1 to 3).

Piperidyl group (in the piperidine ring, (n-1) phenyl group [in the phenyl ring at least one group -NR ^{26 '} R ^27' (R ^{26 '} is a hydrogen atom or a C 1-6 alkyl group R ^{27 ′} represents a phenyl group [a group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group on the phenyl ring And at least one of them may be substituted])) is substituted.], (N-2) group -W ₁ NR ^{28 '} R ^29' [W ₁ is a C 1-6 alkylene group] R ^{28 ′} represents a hydrogen atom or a C1-6 alkyl group R ^{29 ′} represents a phenyl group (on a phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted group Or a group selected from the group consisting of unsubstituted C.sub.1-6 alkoxy groups C1-6 alkoxy group substituted by two (n-3) phenyl groups [in the phenyl ring, a halogen atom, halogen substituted or unsubstituted. At least one of a group selected from the group consisting of a C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group may be substituted] and a (n-4) phenyl C1-6 alkyl group [ At least one phenyl group on the phenyl group ring (from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group on the phenyl ring) As at least one kind of a group selected from the group consisting of a group consisting of], at least one kind of selected groups may be substituted), for example, (1 , 2-, 3- or 4-) piperidyl group, 4- [N-methyl-N- (4-trifluoromethoxyphenyl) amino] phenyl-1-piperidyl group, 4- [N- (4-trifluoromethoxy) Phenyl) aminomethyl] -1-piperidyl group, 4- [N-methyl-N- (4-trifluoromethoxyphenyl) aminomethyl] -1-piperidyl group, 4- [N-ethyl-N- (4-tri] Fluoromethoxyphenyl) aminomethyl] -1-piperidyl group, 4- [1,1-di (4-trifluoromethoxyphenyl) methoxy] -1-piperidyl group, 4- [N-methyl-N- (4-tributyl group Fluoromethylphenyl) amino] phenyl-1-piperidyl group, 4- [N- (4-trifluoromethylphenyl) aminomethyl] -1-piperidyl group, 4- {N-methyl- -[2,4-di (trifluoromethyl) phenyl] aminomethyl} -1-piperidyl group, 4- {N-ethyl-N- [2,4,6-tri (trifluoromethoxy) phenyl] aminomethyl} -1-piperidyl group, 4- [1,1-di (4-trifluoromethylphenyl) methoxy] -1-piperidyl group, 4- [N-methyl-N- (4-chlorophenyl) amino] phenyl-1- Piperidyl group, 4- [N- (2,4-dibromophenyl) aminomethyl] -1-piperidyl group, 4- [N-methyl-N- (2,4,6-trifluorophenyl) aminomethyl] -1 -Piperidyl group, 4- [N-ethyl-N- (4-chlorophenyl) aminomethyl] -1-piperidyl group, 4- [1,1-di (4-chlorophenyl) methoxy] -1-piperidyl group, 4- [N -Methyl-N- (2,4-dibromophenyl) amino] phenyl-1-piperidyl group, 4- [1,1-di (2,4-dibromophenyl) methoxy] -1-piperidyl group, 4- [N -Methyl-N- (2,4,6-trifluorophenyl) amino] phenyl-1-piperidyl group, 4- [1,1-di (2,4,6-trifluorophenyl) methoxy] -1- Piperidyl group, 4- {N-methyl-N- [2,4-di (trifluoromethyl) phenyl] amino} phenyl-1-piperidyl group, 4- {N-methyl-N- [2,4,6- Tri (trifluoromethoxy) phenyl] amino} phenyl-1-piperidyl group, 4- {1- [2,4-di (trifluoromethyl) phenyl] -1- [2,4,6-tri (trifluoromethoxy) ) Phenyl] methoxy}- -Piperidyl group, 4- [N- (4-trifluoromethoxyphenyl) aminomethyl] -3- [N- (4-trifluoromethylphenyl) aminomethyl] -1-piperidyl group, 3,4,6-triperyl group Piperidyl groups such as (1,1-diphenylmethoxy) -1-piperidyl group, 4- (4-phenylbenzyl)-(1-, 2- or 3-) piperidyl group (on the piperidine ring, (n-1 ) Phenyl group [in the phenyl ring, 1 to 3 groups -NR ^{26 '} R ^27' (R ^{26 '} represents a hydrogen atom or a C 1-6 alkyl group. R ^{27 ′} is a group selected from the group consisting of a halogen group, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group on a phenyl group [phenyl ring To 5 and preferably 1 to 3 may be substituted]. ) Is assumed to be substituted. ] Indicates the (n-2) group _{^{-W 1 NR 28 'R 29'}} [W 1 is C1~6 alkylene group. R ^{28 ′} represents a hydrogen atom or a C1-6 alkyl group. R ^{29 ′} is a phenyl group (on the phenyl ring, a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group is To 5 and preferably 1 to 3 may be substituted). ], (N-3) a C1-6 alkoxy group substituted by two phenyl groups [in the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 Groups selected from the group consisting of alkoxy groups may be substituted by 1 to 5, preferably 1 to 3) and (n-4) phenyl C1-6 alkyl groups [on the phenyl ring 1 A group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group on the phenyl ring And 5 groups, preferably 1 to 3 groups, may be substituted), and 1 to 3 groups selected from the group consisting of .

  C 1 to C 6 alkyl group substituted with two phenyl groups [on the phenyl ring, selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C 1 to 6 alkyl group and a halogen substituted or unsubstituted C 1 to 6 alkoxy group As at least one kind of the substituted groups] may be, for example, 1,1-diphenylmethyl group, 1,2-diphenylethyl group, 3,3-diphenylpropyl group, 3,4-diphenyltyl group Group, 3,5-diphenylpentyl group, 4,6-diphenylhexyl group, 1,1-di (4-trifluoromethoxyphenyl) methyl group, 1,1-di (4-chlorophenyl) methyl group, 1- ( 2-fluorophenyl) -1- (3-fluorophenyl) methyl group, 1- (4-fluorophenyl) -1- (2-chlorophenyl) methyl group, 1- (3) Chlorophenyl) -1- (4-chlorophenyl) methyl group, 1- (2-bromophenyl) -1- (3-bromophenyl) methyl group, 1- (4-bromophenyl) -2- (2-iodophenyl) Ethyl group, 3- (3-iodophenyl) -3- (4-iodophenyl) propyl group, 1- (2,3-difluorophenyl) -1- (3,4-difluorophenyl) methyl group, 4- (4- 3,5-difluorophenyl) -4- (2,4-difluorophenyl) butyl, 5- (2,6-difluorophenyl) -5- (2,3-dichlorophenyl) pentyl, 6- (3,4 -Dichlorophenyl) -6- (3,5-dichlorophenyl) hexyl group, 1- (2,4-dichlorophenyl) -1- (2,6-dichlorophenyl) methyl group, 1- (3,4,5-triyl) Fluorophenyl) -1- (3,4,5-trichlorophenyl) methyl group, 1- (2,3,4,5,6-pentafluorophenyl) -1- (2,4,6-trimethylphenyl) methyl group 1- (4-n-butylphenyl) -1- (2,4-dimethylphenyl) methyl group, 1- (3,5-ditrifluoromethylphenyl) -1- (4-n-butoxyphenyl) methyl group 1- (2,4-dimethoxyphenyl) -1- (2,3-dimethoxyphenyl) methyl group, 1- (2,4,6-trimethoxyphenyl) -1- (3,5-ditrifluoromethoxyphenyl) ) Methyl group, 1- (3-chloro-4-methoxyphenyl) -1- (2-chloro-4-trifluoromethoxyphenyl) methyl group, 1- (3-methyl-4-fluorophenyl) -1- ( 4-bro Mo-3-trifluoromethylphenyl) methyl group, 1- (2-methylphenyl) -1- (3-methylphenyl) methyl group, 1- (2-pentafluoroethylphenyl) -1- (3-pentafluoro Ethylphenyl) methyl group, 1- (2-isopropylphenyl) -1- (2-tert-butylphenyl) methyl group, 1- (2-sec-butylphenyl) -1- (2-n-heptafluoropropylphenyl) ) Methyl group, 1- (4-n-pentylphenyl) -1- (4-n-hexylphenyl) methyl group, 1- (2-methoxyphenyl) -1- (2,6-dimethoxyphenyl) methyl group, 1- (2-pentafluoroethoxyphenyl) -1- (isopropoxyphenyl) methyl group, 1- (2-tert-butoxyphenyl) -1- (2-sec- 1- (2-n-heptafluoropropoxyphenyl) -1- (4-n-pentoxyphenyl) methyl group, 1,1-di (4-n-hexyloxyphenyl) methyl group, etc. C1-6 alkyl group in which two phenyl groups are substituted [on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group 1 to 5, preferably 1 to 3 selected groups may be substituted].

  A phenoxy group (in which at least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group is substituted on a phenyl ring; Are selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group as defined above. Phenoxy group having 5 to 5, preferably 1 to 3 groups, for example, 2-fluorophenoxy group, 3-fluorophenoxy group, 4-fluorophenoxy group, 2-chlorophenoxy group, 3-chlorophenoxy group, 4 -Chlorophenoxy group, 2-bromophenoxy group, 3-bromophenoxy group, 4-bromophenoxy group, 2-y Dephenoxy group, 3-iodophenoxy group, 4-iodophenoxy group, 2,3-difluorophenoxy group, 3,4-difluorophenoxy group, 3,5-difluorophenoxy group, 2,4-difluorophenoxy group, 2, 6-difluorophenoxy group, 2,3-dichlorophenoxy group, 3,4-dichlorophenoxy group, 3,5-dichlorophenoxy group, 2,4-dichlorophenoxy group, 2,6-dichlorophenoxy group, 3,4, 5-trifluorophenoxy group, 3,4,5-trichlorophenoxy group, 2,4,6-trifluorophenoxy group, 2,4,6-trichlorophenoxy group, 2-fluoro-4-bromophenoxy group, 4- Chloro-3-fluorophenoxy group, 2,3,4-trichlorophenoxy group, 3,4,5-trifluoropheno , 2,3,4,5,6-pentafluorophenoxy, 2,4,6-trimethylphenoxy, 4-n-butylphenoxy, 2,4-dimethylphenoxy, 2,3-dimethylphenoxy Group, 2,6-dimethylphenoxy group, 3,5-dimethylphenoxy group, 2,5-dimethylphenoxy group, 3,5-ditrifluoromethylphenoxy group, 4-n-butoxyphenoxy group, 2,4-dimethoxyphenoxy group Group, 2,3-dimethoxyphenoxy group, 2,6-dimethoxyphenoxy group, 3,5-dimethoxyphenoxy group, 2,5-dimethoxyphenoxy group, 2,4,6-trimethoxyphenoxy group, 3,5-ditrile Fluoromethoxyphenoxy group, 3-chloro-4-methoxyphenoxy group, 2-chloro-4-trifluoromethoxyphenoxy Group, 3-methyl-4-fluorophenoxy group, 4-bromo-3-trifluoromethylphenoxy group, 2-methylphenoxy group, 3-methylphenoxy group, 4-methylphenoxy group, 2-methyl-3-chlorophenoxy Group, 3-methyl-4-chlorophenoxy group, 2-chloro-4-methylphenoxy group, 2-methyl-3-fluorophenoxy group, 2-trifluoromethylphenoxy group, 3-trifluoromethylphenoxy group, 4- Trifluoromethyl phenoxy group, 2-pentafluoroethyl phenoxy group, 3-pentafluoroethyl phenoxy group, 4-pentafluoroethyl phenoxy group, 2-isopropyl phenoxy group, 3-isopropyl phenoxy group, 4-isopropyl phenoxy group, 2- tert-Butylphenoxy group, 3-tert Butylphenoxy group, 4-tert-butylphenoxy group, 2-sec-butylphenoxy group, 3-sec-butylphenoxy group, 4-sec-butylphenoxy group, 2-n-heptafluoropropylphenoxy group, 3-n- Heptafluoropropylphenoxy group, 4-n-heptafluoropropylphenoxy group, 4-n-pentylphenoxy group, 4-n-hexylphenoxy group, 2-methoxyphenoxy group, 3-methoxyphenoxy group, 4-methoxyphenoxy group, 3-chloro-2-methoxyphenoxy group, 2-fluoro-3-methoxyphenoxy group, 2-fluoro-4-methoxyphenoxy group, 2,6-dimethoxyphenoxy group, 2,3,4-trifluorophenoxy group, 2 , 4,6-Trifluorophenoxy group, 2-Trifluorome Xyphenoxy group, 3-trifluoromethoxyphenoxy group, 4-trifluoromethoxyphenoxy group, 3-fluoro-2-trifluoromethoxyphenoxy group, 2-fluoro-3-trifluoromethoxyphenoxy group, 3-fluoro-4- Trifluoromethoxyphenoxy group, 3-chloro-2-trifluoromethoxyphenoxy group, 2-chloro-3-trifluoromethoxyphenoxy group, 3-chloro-4-trifluoromethoxyphenoxy group, 2-pentafluoroethoxyphenoxy group, 3-pentafluoroethoxyphenoxy group, 4-pentafluoroethoxyphenoxy group, 3-chloro-2-pentafluoroethoxyphenoxy group, 2-chloro-3-pentafluoroethoxyphenoxy group, 3-chloro-4-pentafluoroethoxyphene Nooxy group, 2-isopropoxyphenoxy group, 3-isopropoxyphenoxy group, 4-isopropoxyphenoxy group, 2-tert-butoxyphenoxy group, 3-tert-butoxyphenoxy group, 4-tert-butoxyphenoxy group, 2- sec-Butoxyphenoxy group, 3-sec-butoxyphenoxy group, 4-sec-butoxyphenoxy group, 2-n-heptafluoropropoxyphenoxy group, 3-n-heptafluoropropoxyphenoxy group, 4-n-heptafluoropropoxyphenoxy group Groups, 4-n-pentoxyphenoxy group, 4-n-hexyloxyphenoxy group etc. can be mentioned.

  Phenyl C1-6 alkyl group [in the phenyl ring there are at least one phenoxy group (on the phenyl ring a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 Examples of the group in which at least one group selected from the group consisting of alkoxy groups is substituted) are, for example, 4- (4-trifluoromethoxyphenyl) benzyl group, 2,4-di (4-trifluoromethoxyphenyl) benzyl group, 2- (3-trifluoromethylphenoxy) benzyl group, 4- (2-fluorophenoxy) benzyl group, 2,4,6-tri (2-) Fluorophenoxy) benzyl group, 3- (4-chlorophenoxy) benzyl group, 4- (4-methoxyphenoxy) benzyl group, 3- (4- (4-methoxyphenoxy) benzyl group And 2- (3,4-dimethoxyphenoxy) benzyl group; 4- (3,4-dimethylphenoxy) benzyl group; 3- (3,4,6-trimethoxyphenoxy) benzyl group; (2,4,5-trimethylphenoxy) benzyl group, 4- (3,4-dichlorophenoxy) benzyl group, 2- (2,4,6-trifluorophenoxy) benzyl group, 4- (3-chloro-4) -Trifluoromethoxyphenoxy) benzyl group, 2- [4- (2-fluorophenoxy) phenyl] ethyl group, 3- [2- (3,4-dimethoxyphenoxy) phenyl] propyl group, 4- [2- (2) , 4,5-Trimethylphenoxy) phenyl] butyl group, 5- [4- (3-chloro-4-trifluoromethoxyphenoxy) phenyl] pentyl group, 6 A linear or branched C1-C6 alkyl moiety such as [2- (3-trifluoromethylphenoxy) phenyl] hexyl group, 1- [4- (4-trifluoromethoxyphenoxy) phenyl] ethyl group, etc. C 1 -C 6 alkyl group which is a cyclic alkyl group [1 to 3 phenoxy groups on the phenyl ring (a halogen atom, a halogen substituted or unsubstituted C 1 to 6 alkyl group and a halogen substituted or substituted on the phenyl ring Groups substituted by 1 to 3 groups selected from the group consisting of unsubstituted C.sub.1-6 alkoxy groups are substituted.

  As a thiazolyl group (on the thiazole ring, at least one phenyl group may be substituted), for example, (2-, 4- or 5-) thiazolyl group, 2-phenyl- (4- or 5) -) Thiazolyl group, 4-phenyl- (2- or 5-) thiazolyl group, 5-phenyl- (2- or 4-) thiazolyl group, 2, 5-diphenyl-4- thiazolyl group, 2,4- diphenyl- Mention may be made of thiazolyl groups such as 5-thiazolyl group and 4,5-diphenyl-2-thiazolyl group (one or two phenyl groups may be substituted on the thiazol ring).

A phenoxy C1-6 alkyl group (on the phenyl ring, the phenyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group At least one group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group Examples of the phenoxy C1-6 alkyl group (a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group, and a halogen-substituted or unsubstituted C1 alkyl group include: To 6) at least one of a group selected from the group consisting of alkoxy groups may be substituted Phenylphenoxymethyl group, 3-phenylphenoxymethyl group, 2-phenylphenoxymethyl group, 2,4-diphenylphenoxymethyl group, 2,4,6-triphenylphenoxymethyl group, 4- (4-trifluoromethoxyphenyl) Phenoxymethyl group, 2- (3-trifluoromethylphenyl) phenoxymethyl group, 4- (2-fluorophenyl) phenoxymethyl group, 3- (4-chlorophenyl) phenoxymethyl group, 4- (4-methoxyphenyl) phenoxy Methyl group, 3- (4-methylphenyl) phenoxymethyl group, 2- (3,4-dimethoxyphenyl) phenoxymethyl group, 4- (3,4-dimethylphenyl) phenoxymethyl group, 3- (3,4,6 6-trimethoxyphenyl) phenoxymethyl group, 2- (2,4,5-) Rymethylphenyl) phenoxymethyl group, 4- (3,4-dichlorophenyl) phenoxymethyl group, 2- (2,4,6-trifluorophenyl) phenoxymethyl group, 4- (3-chloro-4-trifluoromethoxy Phenyl) phenoxymethyl group, 2- (4-phenylphenoxy) ethyl group, 2- [4- (2-fluorophenyl) phenoxy] ethyl group, 3- [2- (3,4-dimethoxyphenyl) phenoxy] propyl group , 4- [2- (2,4,5-trimethylphenyl) phenoxy] butyl group, 5- [4- (3-chloro-4-trifluoromethoxyphenyl) phenoxy] pentyl group, 6- [2- (3) -Trifluoromethylphenyl) phenoxy] hexyl group, 2- [4- (4-trifluoromethylphenyl) phenoxy] ethyl group, 2 A phenoxy C1-6 alkyl group in which the alkyl moiety such as-[4- (4-trifluoromethoxyphenyl) phenoxy] ethyl group is a linear or branched alkyl group having 1 to 6 carbon atoms (on the phenyl ring Phenyl group (in the phenyl ring, 1 to 5 groups selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group, A group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group, and a halogen-substituted or unsubstituted C1-6 alkoxy group, which is preferably 1 to 3 substituted; Cphenyl C2-6 alkenyl group [in the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and At least one member selected from the group consisting of a halogen-substituted or unsubstituted C1-6 alkoxy group is substituted with a halogen atom, a halogen C1-6 alkyl group, and a halogen-substituted or unsubstituted group; And an alkenyl group having 1 to 2 and preferably 1 to 3 substituted phenyl groups having 1 to 3 carbon atoms and 2 to 6 carbon atoms each having 2 to 6 carbon atoms. A group consisting of The phenyl C2-6 alkenyl group includes both trans and cis forms. As such a phenyl C2-6 alkenyl group, for example, 3- (2-fluorophenyl) -2-propenyl group, 3,3-di (2-fluorophenyl) -2-propenyl group, 3- (3- (3- (3-) Fluorophenyl) -2-propenyl group, 3- (4-fluorophenyl) -2-propenyl group, 3- (2,3-difluorophenyl) -2-propenyl group, 3- (2,3,4,5, 6-pentafluorophenyl) -2-propenyl group, 3- (2,4-difluorophenyl) -2-propenyl group, 3- (3,4-difluorophenyl) -2-propenyl group, 3- (3,5 -Difluorophenyl) -2-propenyl group, 3- (2-chlorophenyl) -2-propenyl group, 3- (3-chlorophenyl) -2-propenyl group, 3- (4-chlorophenyl) -2-propane Penyl group, 3- (2,3-dichlorophenyl) -2-propenyl group, 3- (2,4-dichlorophenyl) -2-propenyl group, 3- (3,4-dichlorophenyl) -2-propenyl group, 3- (3,5-dichlorophenyl) -2-propenyl group, 3- (2-bromophenyl) -2-propenyl group, 3- (3-bromophenyl) -2-propenyl group, 3- (4-bromophenyl)- 2-propenyl group, 3- (2-methylphenyl) -2-propenyl group, 3- (3-methylphenyl) -2-propenyl group, 3- (4-methylphenyl) -2-propenyl group, 3- (3- (4-methylphenyl) -2-propenyl group 2-trifluoromethylphenyl) -2-propenyl group, 3- (2-fluoro-4-bromophenyl) -2-propenyl group, 3- (4-chloro-3-fluorophenyl) -2-prope group And 3- (2,3,4-trichlorophenyl) -2-propenyl, 3- (2,4,6-trichlorophenyl) -2-propenyl and 3- (4-isopropylphenyl) -2- Propenyl group, 3- (4-n-butylphenyl) -2-propenyl group, 3- (2,4-dimethylphenyl) -2-propenyl group, 3- (2,3-dimethylphenyl) -2-propenyl group 3- (2,6-dimethylphenyl) -2-propenyl group, 3- (3,5-dimethylphenyl) -2-propenyl group, 3- (2,5-dimethylphenyl) -2-propenyl group, 3 -(2,4,6-trimethylphenyl) -2-propenyl group, 3- (3,5-ditrifluoromethylphenyl) -2-propenyl group, 3- (4-n-butoxyphenyl) -2-propenyl group , 3- (2 , 4-Dimethoxyphenyl) -2-propenyl group, 3- (2,3-dimethoxyphenyl) -2-propenyl group, 3- (2,6-dimethoxyphenyl) -2-propenyl group, 3- (3,5 -Dimethoxyphenyl) -2-propenyl group, 3- (2,5-dimethoxyphenyl) -2-propenyl group, 3- (3,5-ditrifluoromethoxyphenyl) -2-propenyl group, 3- (3-chloro) -4-methoxyphenyl) -2-propenyl group, 3- (2-chloro-4-trifluoromethoxyphenyl) -2-propenyl group, 3- (3-methyl-4-fluorophenyl) -2-propenyl group, 3- (4-bromo-3-trifluoromethylphenyl) -2-propenyl group, 3- (3-trifluoromethylphenyl) -2-propenyl group, 3- (4-trifluro) Methylphenyl) -2-propenyl group, 3- (2-trifluoromethoxyphenyl) -2-propenyl group, 3- (3-trifluoromethoxyphenyl) -2-propenyl group, 3- (4-trifluoromethoxy) Phenyl) -2-propenyl group, 3- (2-methoxyphenyl) -2-propenyl group, 3- (3-methoxyphenyl) -2-propenyl group, 3- (4-methoxyphenyl) -2-propenyl group, 3- (3,4-dimethoxyphenyl) -2-propenyl group, 3- (3,5-dimethoxyphenyl) -2-propenyl group, 4- (4-chlorophenyl) -2-butenyl group, 4- (4- (4-chlorophenyl) -2-butenyl group) Chlorophenyl) -3-butenyl group, 5- (4-chlorophenyl) -2-pentenyl group, 5- (4-chlorophenyl) -4-pentenyl group, 5- (4-chloro) 6- (4-chlorophenyl) -3-hexenyl group, 6- (4-chlorophenyl) -3-hexenyl group, 6- (4-chlorophenyl) -3-hexenyl group, 6- (phenyl) -3-pentenyl group 4-chlorophenyl) -3-hexenyl group etc. can be mentioned.

  Imidazolyl group [in which at least one phenyl group (on the phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group are formed on the phenyl ring Group (s) may be substituted), for example, (1-, 2-, 4- or 5-) imidazolyl group, 1-phenyl 2-imidazolyl group, 2- (2-fluorophenyl) -1-imidazolyl group, 4- (3-fluorophenyl) -2-imidazolyl group, 5- (4-fluorophenyl) -3-imidazolyl group, 1- (2-chlorophenyl) -3-imidazolyl group, 2- (3-chlorophenyl) -5-imidazolyl group, 1- (4-chlorophenyl) -2-imidazolyl group 4- (2-bromophenyl) -5-imidazolyl group, 5- (3-bromophenyl) -2-imidazolyl group, 1- (4-bromophenyl) -3-imidazolyl group, 2- (2-iodophenyl) 4-imidazolyl group, 4- (3-iodophenyl) -5-imidazolyl group, 5- (4-iodophenyl) -1-imidazolyl group, 1- (2,3-difluorophenyl) -2-imidazolyl group, 1- (3,4-difluorophenyl) -2-imidazolyl group, 1- (3,5-difluorophenyl) -2-imidazolyl group, 1- (2,4-difluorophenyl) -4-imidazolyl group, 1- (2,6-difluorophenyl) -5-imidazolyl group, 1- (2,3-dichlorophenyl) -2-imidazolyl group, 1- (3,4-dichloropheny) -4-imida Ryl group, 1- (3,5-dichlorophenyl) -5-imidazolyl group, 1- (2,4-dichlorophenyl) -2-imidazolyl group, 1- (2,6-dichlorophenyl) -4-imidazolyl group, 1- (3,4,5-trifluorophenyl) -5-imidazolyl group, 1- (3,4,5-trichlorophenyl) -2-imidazolyl group, 1- (2,4,6-trifluorophenyl) -4 -Imidazolyl, 1- (2,4,6-trichlorophenyl) -5-imidazolyl, 1- (2-fluoro-4-bromophenyl) -2-imidazolyl, 1- (4-chloro-3-fluoro) Phenyl) -4-imidazolyl group, 1- (2,3,4-trichlorophenyl) -5-imidazolyl group, 1- (2,3,4,5,6-pentafluorophenyl) -2-imidazolyl Group, 1- (2,4,6-trimethylphenyl) -2-imidazolyl group, 2- (4-n-butylphenyl) -4-imidazolyl group, 4- (2,4-dimethylphenyl) -1-imidazolyl group Group, 5- (2,3-dimethylphenyl) -2-imidazolyl group, 1- (2,6-dimethylphenyl) -4-imidazolyl group, 2- (3,5-dimethylphenyl) -5-imidazolyl group, 4- (2,5-dimethylphenyl) -1-imidazolyl group, 5- (3,5-ditrifluoromethylphenyl) -2-imidazolyl group, 1- (4-n-butoxyphenyl) -2-imidazolyl group, 1- (2,4-dimethoxyphenyl) -2-imidazolyl group, 1- (2,3-dimethoxyphenyl) -2-imidazolyl group, 1- (2,6-dimethoxyphenyl) -2-imidazo And 2- (3,5-dimethoxyphenyl) -4-imidazolyl, 4- (2,5-dimethoxyphenyl) -1-imidazolyl, 5- (2,4,6-trimethoxyphenyl) -2 -Imidazolyl group, 1- (3,5-ditrifluoromethoxyphenyl) -2-imidazolyl group, 1- (3-chloro-4-methoxyphenyl) -2-imidazolyl group, 1- (2-chloro-4-triyl group) Fluoromethoxyphenyl) -2-imidazolyl group, 1- (3-methyl-4-fluorophenyl) -2-imidazolyl group, 1- (4-bromo-3-trifluoromethylphenyl) -2-imidazolyl group, 1- (2-methylphenyl) -2-imidazolyl group, 2- (3-methylphenyl) -4-imidazolyl group, 4- (4-methylphenyl) -5-imidazolyl group, 5 (2-methyl-3-chlorophenyl) -1-imidazolyl group, 1- (3-methyl-4-chlorophenyl) -2-imidazolyl group, 2- (2-chloro-4-methylphenyl) -4-imidazolyl group, 4- (2-methyl-3-fluorophenyl) -5-imidazolyl group, 5- (2-trifluoromethylphenyl) -1-imidazolyl group, 1- (3-trifluoromethylphenyl) -2-imidazolyl group, 2- (4-trifluoromethylphenyl) -4-imidazolyl group, 4- (2-pentafluoroethylphenyl) -5-imidazolyl group, 5- (3-pentafluoroethylphenyl) -1-imidazolyl group, 1- (4-Pentafluoroethylphenyl) -2-imidazolyl group, 2- (2-isopropylphenyl) -4-imidazolyl group, 4- (3) -Isopropylphenyl) -5-imidazolyl group, 5- (4-isopropylphenyl) -1-imidazolyl group, 1- (2-tert-butylphenyl) -2-imidazolyl group, 2- (3-tert-butylphenyl) -4-imidazolyl group, 4- (4-tert-butylphenyl) -5-imidazolyl group, 5- (2-sec-butylphenyl) -1-imidazolyl group, 1- (3-sec-butylphenyl) -2 -Imidazolyl group, 2- (4-sec-butylphenyl) -4-imidazolyl group, 4- (2-n-heptafluoropropylphenyl) -5-imidazolyl group, 5- (3-n-heptafluoropropylphenyl) -1-imidazolyl group, 1- (4-n-heptafluoropropylphenyl) -2-imidazolyl group, 2- (4-pentyl) group Nyl) -4-imidazolyl group, 4- (4-hexylphenyl) -5-imidazolyl group, 1- (2-methoxyphenyl) -2-imidazolyl group, 5- (3-methoxyphenyl) -1-imidazolyl group, 1- (4-methoxyphenyl) -2-imidazolyl group, 2- (3-chloro-2-methoxyphenyl) -4-imidazolyl group, 4- (2-fluoro-3-methoxyphenyl) -5-imidazolyl group, 5- (2-fluoro-4-methoxyphenyl) -1-imidazolyl group, 1- (2,6-dimethoxyphenyl) -2-imidazolyl group, 1- (2,3,4-trifluorophenyl) -2- Imidazolyl group, 1- (2-trifluoromethoxyphenyl) -2-imidazolyl group, 2- (3-trifluoromethoxyphenyl) -4-imidazolyl group, 1- 4-trifluoromethoxyphenyl) -2-imidazolyl group, 1- (3-fluoro-2-trifluoromethoxyphenyl) -2-imidazolyl group, 1- (2-fluoro-3-trifluoromethoxyphenyl) -2- Imidazolyl group, 1- (3-fluoro-4-trifluoromethoxyphenyl) -2-imidazolyl group, 1- (3-chloro-2-trifluoromethoxyphenyl) -2-imidazolyl group, 1- (2-chloro-) 3-trifluoromethoxyphenyl) -2-imidazolyl group, 1- (3-chloro-4-trifluoromethoxyphenyl) -2-imidazolyl group, 1- (2-pentafluoroethoxyphenyl) -2-imidazolyl group, 1 -(3-pentafluoroethoxyphenyl) -2-imidazolyl group, 1- (4-pentafluoroethoxy) Phenyl) -2-imidazolyl group, 1- (3-chloro-2-pentafluoroethoxyphenyl) -2-imidazolyl group, 1- (2-chloro-3-pentafluoroethoxyphenyl) -2-imidazolyl group, 1- (3-chloro-4-pentafluoroethoxyphenyl) -2-imidazolyl group, 1- (2-isopropoxyphenyl) -2-imidazolyl group, 1- (3-isopropoxyphenyl) -2-imidazolyl group, 1- (4-isopropoxyphenyl) -2-imidazolyl group, 1- (2-tert-butoxyphenyl) -2-imidazolyl group, 1- (3-tert-butoxyphenyl) -2-imidazolyl group, 1- (4- (4-tert-butoxyphenyl) -2-imidazolyl group) tert-butoxyphenyl) -2-imidazolyl group, 1- (2-sec-butoxyphenyl) -2-imidazolyl group, -(3-sec-butoxyphenyl) -2-imidazolyl group, 1- (4-sec-butoxyphenyl) -2-imidazolyl group, 1- (2-n-heptafluoropropoxyphenyl) -2-imidazolyl group, 1 -(3-n-heptafluoropropoxyphenyl) -2-imidazolyl group, 1- (4-n-heptafluoropropoxyphenyl) -2-imidazolyl group, 1- (4-n-pentoxyphenyl) -2-imidazolyl group , An imidazolyl group such as 1- (4-n-hexyloxyphenyl) -2-imidazolyl group, 1,4-diphenyl-2-imidazolyl group, 1,4,5-triphenyl-2-imidazolyl group [imidazole ring Above, 1 to 3 phenyl groups (on the phenyl ring, halogen atoms, halogen substituted or unsubstituted C1-6 alkyl And 1 to 5, preferably 1 to 3 groups selected from the group consisting of halogen-substituted or unsubstituted C1-6 alkoxy groups may be substituted). Can.

  Piperazinyl group (C.sub.1-6 alkyl group substituted by two phenyl groups on the piperazine ring [a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C1. 66 alkoxy group, at least one of a group selected from the group consisting of an alkoxy group may be substituted], phenyl C1-6 alkyl group [in the phenyl ring, at least one phenoxy group (in the phenyl ring And at least one group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group is substituted Thiazolyl group [at least one phenyl group may be substituted on the thiazole ring], phenoxyl group C1-6 alkyl group [a phenyl group (a group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group on a phenyl ring At least one of the selected groups may be substituted), a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group; [C2-6 alkenyl group] [in the phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1 group; It is assumed that at least one group selected from the group consisting of -6 alkoxy groups is substituted.] And imidazolyl [At least one phenyl group on the imidazole ring (on the phenyl ring, a group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group. As at least one kind of the group selected from the group consisting of the group consisting of] may be substituted, for example, at least one kind of the selected group may be substituted), for example , 4- [1,1-di (4-chlorophenyl) methyl] -1-piperazinyl group, 4- [1,1-di (4-trifluoromethoxyphenyl) methyl] -1-piperazinyl group, 4- (4 -Chlorocinnamyl) -1-piperazinyl group, 4- (4-trifluoromethoxycinnamyl) -1-piperazinyl group, 4- [1- (4-chlorophenyl) -2-imidazolyl -1-piperazinyl group, 4- [1,1-di (2,4-dibromophenyl) methyl] -1-piperazinyl group, 4- [1,1-di (4-trifluoromethylphenyl) methyl]- 1-piperazinyl group, 4- (2,4-dichlorocinnamyl) -1-piperazinyl group, 4- (4-trifluoromethyl nanamyl) -1-piperazinyl group, 4- {1- [2,4-di] (Trifluoromethoxy) phenyl] -2-imidazolyl} -1-piperazinyl group, 4- [1,1-di (2,4,6-trifluorophenyl) methyl] -1-piperazinyl group, 4- {1, 1 1-di [2,4-di (trifluoromethoxy) phenyl] methyl} -1-piperazinyl group, 4- [2,4,6-tri (trifluoromethyl) cinnamyl] -1-piperazinyl group, 4- [4 2,4-di (tri Luoromethoxy) cinnamyl] -1-piperazinyl group, 4- [1- (4-trifluoromethylphenyl) -2-imidazolyl] -1-piperazinyl group, 4- (2,4,6-trifluorocinnamyl) -1- Piperazinyl group, 4- [1- (2,4-dibromophenyl) -2-imidazolyl] -1-piperazinyl group, 4- [1,1-di (4-chlorophenyl) methyl] -3- (4-chlorocinna) Mil) -1-piperazinyl group, 4- (4-trifluoromethoxycinnamyl) -2- [1- (4-chlorophenyl) -2-imidazolyl] -1-piperazinyl group, 4- (4-trifluoromethoxycinnama) Mil) -2- [1- (4-chlorophenyl) -2-imidazolyl] -6- (1-imidazolyl) -1-piperazinyl group, 4- [4- (4-trifluro] Lomethoxyphenoxy) benzyl]-(1-, 2- or 3-) piperazinyl group, 4- [4-phenyl- (2- or 5-) thiazolyl]-(1-, 2- or 3-) piperazinyl group, 4- [2- (4-trifluoromethoxyphenoxy) ethyl]-(1-, 2- or 3-) piperazinyl group, 4- [2- (4-phenylphenoxy) ethyl]-(1-, 2- or 3-) Piperazinyl group, 4- [2- (4-chlorophenoxy) ethyl]-(1-, 2- or 3-) piperazinyl group, 4- [2- (3,4-dichlorophenol) ethyl]- (1-, 2- or 3-) piperazinyl group, 4- [2- (4-trifluoromethylphenoxy) ethyl]-(1-, 2- or 3-) piperazinyl group, 4- [2- (4- (4-) Trifluoromethoxyphenoxy) ethyl]-( Piperazinyl groups such as 1-, 2- or 3-) piperazinyl groups (C.sub.1-6 alkyl groups substituted with two phenyl groups on the piperazine ring [halogen atoms, halogen substituted or unsubstituted on the phenyl ring, 1 to 5, preferably 1 to 3 groups selected from the group consisting of a C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group may be substituted], phenyl C1-6 alkyl Group [phenyl ring on 1 to 3 phenoxy groups (phenyl ring on halogen ring, halogen substituted or unsubstituted C1-6 alkyl group and halogen substituted or unsubstituted C1-6 alkoxy group It is assumed that 1 to 5, preferably 1 to 3 groups selected from the group are substituted), thiazolyl group [on the thiazole ring, 1 [2 phenyl group may be substituted], phenoxy C1-6 alkyl group [phenyl group (on halogen ring, halogen atom, halogen substituted or unsubstituted C1 to 6 alkyl group on phenyl ring And 1 to 5, preferably 1 to 3 groups selected from the group consisting of halogen substituted or unsubstituted C1-6 alkoxy groups may be substituted), halogen atoms, halogen substituted or unsubstituted C1 1 to 5, preferably 1 to 3 groups selected from the group consisting of -6 alkyl group and halogen substituted or unsubstituted C1-6 alkoxy group may be substituted], phenyl C2-6 alkenyl group [1 to 5, preferably 1 to 5 groups selected from a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group And 1 to 3 substituted phenyl groups each having 1 to 2 or 2 carbon atoms and an alkenyl group having 2 to 6 carbon atoms and 1 to 3 double bonds] and an imidazolyl group [on the imidazole ring, Groups selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group on the phenyl ring It is assumed that 1 to 3 groups selected from the group consisting of 5), preferably 1 to 3 optionally substituted) are substituted. Can be mentioned.

  Anilino C1-6 alkyl group [in which at least one of the groups selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group on a phenyl ring As the species, “N may be substituted with a C1-6 alkyl group at the N-position of the anilino group,” for example, an unsubstituted anilino group or a halogen-substituted or unsubstituted C1 as defined aboveア ニ 6 alkyl group, halogen-substituted or unsubstituted C1-6 alkoxy group, and a group selected from the group consisting of halogen are composed of anilino group and C1-6 alkyl group substituted with 1 to 5, preferably 1 to 3 Groups, for example, anilinomethyl group, N-methyl-N-anilinomethyl group, N-ethyl-N-anilinomethyl group, N-n-propyl-N-a Linomethyl group, Nn-butyl-N-anilinomethyl group, Nn-pentyl-N-anilinomethyl group, N-n-hexyl-N-anilinomethyl group, 2-anilinoethyl group, 3-anilinopropyl group, 4- Anilinobutyl group, 5-anilinopentyl group, 6-anilinohexyl group, 4-fluoroanilinomethyl group, 2-fluoro-4-bromoanilinomethyl group, 4-chloro-3-fluoroanilinomethyl group, 2 , 3,4-trichloroanilinomethyl group, 3,4,5-trichloroanilinomethyl group, 2,4,6-trichloroanilinomethyl group, N-methyl-N-2,4,6-trichloroanilino Methyl, 4-isopropylanilinomethyl, 4-n-butylanilinomethyl, 4-methylanilinomethyl, 2-methylanilinomethyl, 3- Tilanilinomethyl group, 2,4-dimethylanilinomethyl group, 2,3-dimethylanilinomethyl group, 2,6-dimethylanilinomethyl group, 3,5-dimethylanilinomethyl group, 2,5- Dimethylanilinomethyl group, N-methyl-N-2,5-dimethylanilinomethyl group, 2,4,6-trimethylanilinomethyl group, 3,5-ditrifluoromethylanilinomethyl group, 2,3, 4,5,6-pentafluoroanilinomethyl group, 4-isopropoxyanilinomethyl group, 4-n-butoxyanilinomethyl group, 4-methoxyanilinomethyl group, 2-methoxyanilinomethyl group, 3- Methoxyanilinomethyl group, N-methyl-N-3-methoxyanilinomethyl group, 2,4-dimethoxyanilinomethyl group, 2,3-dimethoxyanilinomethyl group, 2, 6- Dimethoxyanilinomethyl group, 3,5-dimethoxyanilinomethyl group, 2,5-dimethoxyanilinomethyl group, 2,4,6-trimethoxyanilinomethyl group, 3,5-ditrifluoromethoxyanilinomethyl group 2-isopropoxyanilinomethyl group, 3-chloro-4-methoxyanilinomethyl group, 2-chloro-4-trifluoromethoxyanilinomethyl group, 3-methyl-4-fluoroanilinomethyl group, 4- Bromo-3-trifluoromethylanilinomethyl group, 2- (4-fluoroanilino) ethyl group, 3- (4-fluoroanilino) propyl group, 4- (4-fluoroanilino) butyl group, 5- (4-fluoroanilino) pentyl, 6- (4-fluoroanilino) hexyl, 4-chloroanilinomethyl, 2- (4-chloroanilino) Ethyl, 3- (4-chloroanilino) propyl, 4- (4-chloroanilino) butyl, 5- (4-chloroanilino) pentyl, 6- (4-chloroanilino) hexyl, 4-methylanilinomethyl , 2- (4-Methylanilino) ethyl, 3- (4-Methylanilino) propyl, 4- (4-Methylanilino) butyl, 5- (4-Methylanilino) pentyl, 6- (4-Methylanilino) hexyl , 4-trifluoromethylanilinomethyl group, 2- (4-trifluoromethylanilino) ethyl group, 3- (4-trifluoromethylanilino) propyl group, 4- (4-trifluoromethylanilino) Butyl group, N-methyl-N- [4- (4-trifluoromethylanilino)] butyl group, 5- (4-trifluoromethylanilino) N'tynyl group, 6- (4-trifluoromethylanilino) hexyl group, 4-trifluoromethoxyanilinomethyl group, N-methyl-N-4-trifluoromethoxyanilinomethyl group, 2- (4-trifluoro) Methoxyanilino) ethyl group, 3- (4-trifluoromethoxyanilino) propyl group, 4- (4-trifluoromethoxyanilino) butyl group, 5- (4-trifluoromethoxyanilino) pentyl group, 6 -(4-trifluoromethoxyanilino) hexyl, 4-methoxyanilinomethyl, 2- (4-methoxyanilino) ethyl, 3- (4-methoxyanilino) propyl, 4- (4- Examples thereof include methoxyanilino) butyl group, 5- (4-methoxyanilino) pentyl group, 6- (4-methoxyanilino) hexyl group and the like.

  A thiazolyl C.sub.1-6 alkoxy group (on the thiazole ring, a (p-1) phenoxy C.sub.1-6 alkyl group [on a phenyl ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or not. At least one of the groups selected from the group consisting of substituted C1-6 alkoxy groups may be substituted], (p-2) anilino C1-6 alkyl group [on halogen ring, halogen atom, halogen At least one group selected from the group consisting of a substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted], (p-3) phenyl C1 To a group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group on the phenyl ring (P-4) Piperazinyl C1-6 alkyl group [in the piperazine ring, at least one phenyl group (on the phenyl ring, a halogen atom, halogen-substituted or not At least one of a group selected from the group consisting of a substituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted) and (p -5) Piperidyl C1-6 alkyl group [in the piperidine ring, at least one phenoxy group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted At least one group selected from the group consisting of a C1-6 alkoxy group may be substituted)) and at least one group selected from the group consisting of As (4) may be, for example, (2-thiazolyl) methoxy, 2- (4-thiazolyl) ethoxy, 3- (5-thiazolyl) propoxy, 4- (2-thiazolyl) butoxy, 5 -(4-thiazolyl) pentyloxy, 6- (5-thiazolyl) hexyloxy, {4- [4- (4-chlorophenoxy) -1-piperidylmethyl] -2-thiazolyl} methoxy, {4- [4- (4-Trifluoromethylphenoxy) -1-piperidylmethyl] -2-thiazolyl} methoxy, 2-methyl-3- (2-thiazolyl) propoxy, 1,1-dimethyl-2- (2- Thiazolyl) ethoxy group, {4- [4- (4-trifluoromethoxyphenoxy) -1-piperidylmethyl] -2-thiazolyl} methoxy group, [4- {4- [2,4] Di (trifluoromethoxy) phenoxy] -1-piperidylmethyl} -2-thiazolyl] methoxy group, [4- {4- [2,4,6-tri (trifluoromethyl) phenoxy] -1-piperidylmethyl}- 2-thiazolyl] methoxy group, {4- [4- (2,4-dibromophenoxy) -1-piperidylmethyl] -2-thiazolyl} methoxy group, {4- [4- (2,4,6-trifluoro] group Phenoxy) -1-piperidylmethyl] -2-thiazolyl} methoxy, {4- [4- (4-trifluoromethylphenyl) -1-piperazinylmethyl] -2-thiazolyl} methoxy, {4- [4 4- (4-Trifluoromethoxyphenyl) -1-piperazinylmethyl] -2-thiazolyl} methoxy group, {4- [4- (4-chlorophenyl) -1-piperazini] Rumethyl] -2-thiazolyl} methoxy, [4- {4- [2,4-di (trifluoromethyl) phenyl] -1-piperazinylmethyl} -2-thiazolyl] methoxy, [4- {4 -[2,4,6-tri (trifluoromethoxy) phenyl] -1-piperazinylmethyl} -2-thiazolyl] methoxy group, {4- [4- (2,4-dibromophenyl) -1-pipe] Ladinylmethyl] -2-thiazolyl} methoxy, {4- [4- (2,4,6-trifluorophenyl) -1-piperazinylmethyl] -2-thiazolyl} methoxy, 4- (4- (4-) Trifluoromethylphenoxymethyl) -2-thiazolyl group, [4- (4-trifluoromethoxyphenoxymethoxy) -2-thiazolyl] methoxy group, [4- (4-chlorophenoxymethyl) -2-thia] Lyl] methoxy group, {4- [2,4-di (trifluoromethoxy) phenoxymethyl] -2-thiazolyl} methoxy group, {4- [2,4,6-tri (trifluoromethyl) phenoxymethyl]- 2-thiazolyl} methoxy group, [4- (2,4-dibromophenoxymethyl) -2-thiazolyl] methoxy group, [4- (2,4,6-trifluorophenoxymethyl) -2-thiazolyl] methoxy group, [4- (4-Trifluoromethylanilinomethyl) -2-thiazolyl] methoxy, [4- (4-trifluoromethoxyanilinomethoxy) -2-thiazolyl] methoxy, [4- (4-chloroanil) Linomethyl) -2-thiazolyl] methoxy, {4- [2,4-di (trifluoromethoxy) anilinomethyl] -2-thiazolyl} methoxy, { -[2,4,6-tri (trifluoromethyl) anilinomethyl] -2-thiazolyl} methoxy group, [4- (2,4-dibromoanilinomethyl) -2-thiazolyl] methoxy group, [4- (2) , 4,6-Trifluoroanilinomethyl) -2-thiazolyl] methoxy, {4- [3- (4-trifluoromethoxyphenyl) propyl] -2-thiazolyl} methoxy, {4- [3- ( 4-Trifluoromethylphenyl) propyl] -2-thiazolyl} methoxy, {4- [3- (4-chlorophenyl) propyl] -2-thiazolyl} methoxy, [4- (2,4-diiodobenzyl) -2-thiazolyl] methoxy group, [4- (2,4,6-tribromobenzyl) -2-thiazolyl] methoxy group, {4- [2,4-di (trifluoromethoxy) benzyl group [L] -thiazolyl} methoxy, {4- [2,4,6-tri (trifluoromethyl) benzyl] -2-thiazolyl} methoxy, (4,5-dibenzyl-2-thiazolyl) methoxy, Thiazolyl C1-6 alkoxy groups such as (2-phenoxymethyl-4-benzyl-5-thiazolyl) methoxy group, (2,5-dianilinomethyl-4-thiazolyl) methoxy group (on the thiazole ring, phenoxy C1-6 alkyl Group [in the phenyl ring, 1 to 5 groups selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group, preferably 1 to 3 [optionally substituted], anilino C1-6 alkyl group [on the phenyl ring, a halogen atom, halogen substituted or unsubstituted C1-6 1 to 5, preferably 1 to 3 groups selected from the group consisting of an alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted], phenyl C1-6 alkyl group [phenyl There are 1 to 5 groups, preferably 1 to 3 groups selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group on the ring. [Optionally substituted], piperazinyl C1-6 alkyl group [1 to 3 phenyl groups on the piperazine ring (halogen atoms, halogen substituted or unsubstituted C1-6 alkyl group on the phenyl ring And 1 to 5, preferably 1 to 3 groups selected from the group consisting of halogen-substituted or unsubstituted C1-6 alkoxy groups may be substituted] and piperidyl 1 to 6 alkyl groups [on the piperidine ring, 1 to 3 phenoxy groups (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1 to 6 alkyl group and a halogen substituted or unsubstituted C1 to 6 1 to 5, preferably 1 to 3 groups selected from the group consisting of alkoxy groups may be substituted) 1 to 3 groups selected from the group consisting of And may be substituted).

  8-azabicyclo [3.2.1] octyl group (8-azabicyclo [3.2.1] octane ring, at least one phenoxy group [phenyl ring, halogen atom substituted or unsubstituted For example, at least one of a group selected from the group consisting of a C1-6 alkyl group of and a halogen-substituted or unsubstituted C1-6 alkoxy group] may be substituted, for example, 8-azabicyclo [3.2.1] octyl group, 3- (4-trifluoromethoxyphenoxy) -8-azabicyclo [3.2.1] octyl group, 3- (4-trifluoromethylphenoxy) -8 -Azabicyclo [3.2.1] octyl group, 3- (4-chlorophenoxy) -8-azabicyclo [3.2.1] octyl group, 3- (2,4-dichlorophenoxy) -8 Azabicyclo [3.2.1] octyl group, 3- (2,4,6-trichlorophenoxy) -8-azabicyclo [3.2.1] octyl group, 3- (2-bromophenoxy) -8-azabicyclo [ 3.2.1] Octyl group, 3- (3-fluorophenoxy) -8-azabicyclo [3.2.1] octyl group, 3- [2,4-di (trifluoromethoxy) phenoxy] -8-azabicyclo [3.2.1] Octyl group, 3- [2,4,6-tri (trifluoromethoxy) phenoxy] -8-azabicyclo [3.2.1] octyl group, 3- [2,4-di ( Trifluoromethyl) phenoxy] -8-azabicyclo [3.2.1] octyl group, 3- [2,4,6-tri (trifluoromethyl) phenoxy] -8-azabicyclo [3.2.1] octyl group , 3, -Diphenoxy-8-azabicyclo [3.2.1] octyl group, 3,7,6-triphenoxy-8-azabicyclo [3.2.1] octyl group, 3- (4-methoxyphenoxy) -8-azabicyclo [3.2.1] Octyl group, 3- (4-methylphenoxy) -8-azabicyclo [3.2.1] octyl group, 3- (2,4-dimethoxyphenoxy) -8-azabicyclo [3.2 .1] Octyl group, 3- (2,4,6-trimethoxyphenoxy) -8-azabicyclo [3.2.1] octyl group, 3- (2,4-dimethylphenoxy) -8-azabicyclo [3. 2.1] 8-azabicyclo [3.2.1] octyl group (8-azabicyclo such as octyl group, 3- (2,4,6-trimethylphenoxy) -8-azabicyclo [3.2.1] octyl group, etc. [3 .2.1] On the octane ring, 1 to 3 phenoxy groups [on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy 1 to 5 and preferably 1 to 3 groups selected from the group consisting of groups may be substituted).

  As the benzofuryl C1-6 alkyl group (in the benzofuran ring, at least one halogen-substituted or unsubstituted C1-6 alkyl group may be substituted), for example, [(2-, 3-, 4 -, 5-, 6- or 7-) benzofuryl] methyl group, 1-[(2-, 3-, 4-, 5-, 6- or 7-) benzofuryl] ethyl group, 2-[(2-, 3-, 4-, 5-, 6- or 7-) benzofuryl] ethyl group, 3-[(2-, 3-, 4-, 5-, 6- or 7-) benzofuryl] propyl group, 2- [ (2-, 3-, 4-, 5-, 6- or 7-) benzofuryl] propyl group, 4-[(2-, 3-, 4-, 5-, 6- or 7-) benzofuryl] butyl group , 5-[(2-, 3-, 4-, 5-, 6- or 7-) benzofuryl] pentyl group, 4-[(2-, 3-, 4 , 5-, 6- or 7-) benzofuryl] pentyl group, 6-[(2-, 3-, 4-, 5-, 6- or 7-) benzofuryl] hexyl group, 2-methyl-3-[( 2-, 3-, 4-, 5-, 6- or 7-) benzofuryl] propyl group, 1,1-dimethyl-2-[(2-, 3-, 4-, 5-, 6- or 7- ) Benzofuryl] ethyl group, 2-trifluoromethyl- (3-, 4-, 5-, 6- or 7-) benzofurylmethyl group, 5-trifluoromethyl- (2-, 3-, 4-, 6) -Or 7-) benzofuryl methyl group, 4-methyl- (2-, 3-, 5-, 6- or 7-) benzofuryl methyl group, 2,4-dimethyl- (3-, 5-, 6- Or 7-) benzofuryl methyl group, 2,4, 6-trimethyl- (3-, 5- or 7-) benzofuryl methyl group, 4- tri Luomethyl- (2-, 3-, 5-, 6- or 7-) benzofuryl methyl group, 6-trifluoromethyl- (2-, 3-, 4-, 5- or 7-) benzofuryl methyl group etc Benzofuryl C.sub.1-6 alkyl group wherein the alkyl portion of the alkyl group is a C.sub.1-6 linear or branched alkyl group (1 to 3 halogen-substituted or unsubstituted C.sub.1-6 alkyl groups on the benzofuran ring) May be substituted).

  Piperidyl carbonyl C1-6 alkyl group [in the piperidine ring at least one phenoxy group (on the phenyl ring a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1 6) at least one member selected from the group consisting of alkoxy groups may be substituted); for example, (4-phenoxy-1-piperidylcarbonyl) methyl group, 2 -(3-Phenoxy-2-piperidylcarbonyl) ethyl group, 3- (2-phenoxy-3-piperidylcarbonyl) propyl group, 4- (1-phenoxy-4-piperidylcarbonyl) butyl group, 5- (4-phenoxy) group -1-piperidylcarbonyl) pentyl group, 6- (1-phenoxy-2-piperidylcarbonyl) hexyl group, 1 (4-Trifluoromethoxyphenoxy) -4-piperidylcarbonylmethyl group, 4- (4-trifluoromethoxyphenoxy) -1-piperidylcarbonylmethyl group, 4- (4-trifluoromethylphenoxy) -1-piperidylcarbonylmethyl Group, 4- (3-methoxyphenoxy) -1-piperidylcarbonylmethyl group, 1- (2-methylphenoxy) -4-piperidylcarbonylmethyl group, 4- (4-chlorophenoxy) -1-piperidylcarbonylmethyl group, 4- [3,4-di (trifluoromethoxy) phenoxy] -1-piperidylcarbonylmethyl group, 4- [2,4,6-tri (trifluoromethyl) phenoxy] -1-piperidylcarbonylmethyl group, 4- (3,4-Dimethylphenoxy) -1-piperidyl carbonyl ester Group, 4- (2,4,6-trimethoxyphenoxy) -4-piperidylcarbonylmethyl group, 2- (3,4-dichlorophenoxy) -1-piperidylcarbonylmethyl group, 3- (2,4,6 Alkyl moieties such as -tribromophenoxy) -1-piperidylcarbonylmethyl group, (1,2,6-triphenoxy-4-piperidylcarbonyl) methyl group, (2,4-diphenoxy-1-piperidylcarbonyl) methyl group Piperidyl carbonyl C1-6 alkyl group which is a linear or branched alkyl group having 1 to 6 carbon atoms (1 to 3 phenoxy groups on the piperidine ring (halogen atoms on the phenyl ring, halogen substituted Or 1 to 5 groups, preferably selected from the group consisting of unsubstituted C1-6 alkyl groups and halogen-substituted or unsubstituted C1-6 alkoxy groups Or 1 to 3) may be substituted. Can be mentioned.

  Examples of the amino-substituted C1-6 alkyl group which may have a C1-6 alkyl group as a substituent include, for example, aminomethyl group, 2-aminoethyl group, 1-aminoethyl group, 3-aminopropyl group, 4-amino Butyl group, 5-aminopentyl group, 6-aminohexyl group, 2-methyl-3-aminopropyl group, 1,1-dimethyl-2-aminoethyl group, ethylaminomethyl group, 1- (propylamino) ethyl group , 2- (methylamino) ethyl group, 3- (isopropylamino) propyl group, 4- (n-butylamino) butyl group, 5- (n-pentylamino) pentyl group, 6- (n-hexylamino) hexyl And a substituent such as dimethylaminomethyl group, (N-ethyl-N-propylamino) methyl group, 2- (N-methyl-N-hexylamino) ethyl group and the like Which may have one or two a C1~6 alkyl group Te amino -C1~6 alkyl group can be exemplified.

  As the C1-6 alkylene group, for example, methylene, ethylene, trimethylene, 2-methyltrimethylene, 2,2-dimethyltrimethylene, 1-methyltrimethylene, methylmethylene, ethylmethylene, tetramethylene, pentamethylene, hexamethylene And the like.

  Pyridyl C.sub.1-6 alkyl group [in which at least one phenyl group (on the phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1-6 are substituted. Examples of the group optionally substituted by at least one group selected from the group consisting of an alkoxy group may be substituted], for example, in addition to the pyridyl C1-6 alkyl group, 2- (4) -Trifluoromethoxyphenyl)-(3-, 4-, 5- or 6-) pyridylmethyl group, 2- (4-trifluoromethylphenyl)-(3-, 4-, 5- or 6-) pyridylmethyl Group, 2- (4-methoxyphenyl)-(3-, 4-, 5- or 6-) pyridylmethyl group, 2- (4-methylphenyl)-(3-, 4-, 5- or 6-) Pyridylmethyl group, 2- 3-chloro-4-fluorophenyl)-(3-, 4-, 5- or 6-) pyridylmethyl group, 2- (2,4-dimethoxyphenyl)-(3-, 4-, 5- or 6- ) Pyridylmethyl group, 2- (3,4,5-trimethoxyphenyl)-(3-, 4-, 5- or 6-) pyridylmethyl group, 2- (2,4-dimethylphenyl)-(3-) , 4-, 5- or 6-) pyridylmethyl group, 2- (2,4, 6-trimethylphenyl)-(3-, 4-, 5- or 6-) pyridylmethyl group, 2- (2, 4 , 6-Trichlorophenyl)-(3-, 4-, 5- or 6-) pyridylmethyl, 2- (3-chloro-4-trifluoromethoxyphenyl)-(3-, 4-, 5- or 6 -) Pyridylmethyl, 2,4,6-triphenyl- (3- or 5-) pyridylmethyl, A pyridyl C1-6 alkyl group [in which a alkyl moiety such as a 5-diphenyl- (3-, 4- or 6-) pyridylmethyl group is a linear or branched alkyl group having 1 to 6 carbon atoms [a pyridine ring Selected from the group consisting of 1 to 3 phenyl groups (on the phenyl ring, halogen atoms, halogen substituted or unsubstituted C.sub.1-6 alkyl groups and halogen substituted or unsubstituted C.sub.1-6 alkoxy groups. And the group may be substituted), and the group may be substituted by 1 to 5 and preferably 1 to 3).

  Phenyl C1-6 alkoxycarbonyl group [in which at least a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group on a phenyl ring And 1 type may be substituted] is selected from the group consisting of a halogen atom as defined above, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group A group consisting of a phenyl C1-6 alkoxy group optionally substituted with 1 to 5, preferably 1 to 3 alkoxy groups and a carbonyl group, and examples thereof include a benzyloxycarbonyl group and a 2-phenylethoxycarbonyl group , 3-phenylpropoxycarbonyl group, 2-phenylpropoxycarbonyl group, 4-phenylbutoxy cal Group, 5-phenylpentoxy carbonyl group, 4-phenyl pentoxy carbonyl group, 6-phenylhexyloxycarbonyl group, 2-fluorobenzyloxycarbonyl group, 3-fluorobenzyloxycarbonyl group, 4-fluorobenzyloxycarbonyl group , 2- (2-fluorophenyl) ethoxycarbonyl group, 2- (3-fluorophenyl) ethoxycarbonyl group, 2- (4-fluorophenyl) ethoxycarbonyl group, 2-chlorobenzyloxycarbonyl group, 3-chlorobenzyloxy Carbonyl group, 4-chlorobenzyloxycarbonyl group, 2-fluoro-4-bromobenzyloxycarbonyl group, 4-chloro-3-fluorobenzyloxycarbonyl group, 2,3,4-trichlorobenzyloxycarbonyl group, 3,4 5-trifluorobenzyloxycarbonyl group, 2,3,4,5,6-pentafluorobenzyloxycarbonyl group, 2,4,6-trichlorobenzyloxycarbonyl group, 4-isopropylbenzyloxycarbonyl group, 4-n- Butyl benzyloxycarbonyl group, 4-methylbenzyloxycarbonyl group, 2-methylbenzyloxycarbonyl group, 3-methylbenzyloxycarbonyl group, 2,4-dimethylbenzyloxycarbonyl group, 2,3-dimethylbenzyloxycarbonyl group, 2,6-Dimethylbenzyloxycarbonyl group, 3,5-dimethylbenzyloxycarbonyl group, 2,5-dimethylbenzyloxycarbonyl group, 2,4,6-trimethylbenzyloxycarbonyl group, 3,5-ditrifluoromethylbenzyl group Oki A carbonyl group, 4-isopropoxybenzyloxycarbonyl group, 4-n-butoxybenzyloxycarbonyl group, 4-methoxybenzyloxycarbonyl group, 2-methoxybenzyloxycarbonyl group, 3-methoxybenzyloxycarbonyl group, 2,4 -Dimethoxybenzyloxycarbonyl group, 2,3-dimethoxybenzyloxycarbonyl group, 2,6-dimethoxybenzyloxycarbonyl group, 3,5-dimethoxybenzyloxycarbonyl group, 2,5-dimethoxybenzyloxycarbonyl group, 2,4 , 6-trimethoxybenzyloxycarbonyl group, 3,5-ditrifluoromethoxybenzyloxycarbonyl group, 2-isopropoxybenzyloxycarbonyl group, 3-chloro-4-methoxybenzyloxycarbonyl group, 2 Chloro-4-trifluoromethoxybenzyloxycarbonyl group, 3-methyl-4-fluorobenzyloxycarbonyl group, 4-bromo-3-trifluoromethylbenzyloxycarbonyl group, 2- (2-chlorophenyl) ethoxycarbonyl group, 2 -(3-chlorophenyl) ethoxycarbonyl group, 2- (4-chlorophenyl) ethoxycarbonyl group, 2-trifluoromethylbenzyloxycarbonyl group, 3-trifluoromethylbenzyloxycarbonyl group, 4-trifluoromethylbenzyloxycarbonyl group , 2-trifluoromethoxybenzyl oxoxycarbonyl group, 3-trifluoromethoxybenzyloxycarbonyl group, 4-trifluoromethoxybenzyloxycarbonyl group, 2- (2-trifluoromethylphenyl) etoxy group Carbonyl group, 2- (3-trifluoromethylphenyl) ethoxycarbonyl group, 2- (4-trifluoromethylphenyl) ethoxycarbonyl group, 2- (2-trifluoromethoxyphenyl) ethoxycarbonyl group, 2- (3- Trifluoromethoxyphenyl) ethoxycarbonyl group, 2- (4-trifluoromethoxyphenyl) ethoxycarbonyl group, 3- (2-trifluoromethylphenyl) propoxycarbonyl group, 3- (3-trifluoromethylphenyl) propoxycarbonyl group 3- (4-trifluoromethylphenyl) propoxycarbonyl group, 3- (2-trifluoromethylphenyl) propoxycarbonyl group, 3- (3-trifluoromethoxyphenyl) propoxycarbonyl group, 3- (4-trifluoro) Methoxypheny (4) propoxycarbonyl group, 4- (3-trifluoromethylphenyl) butoxycarbonyl group, 5- (4-trifluoromethylphenyl) pentoxy carbonyl group, 4- (4-trifluoromethylphenyl) pentoxy carbonyl group, 4- (4-trifluoromethoxyphenyl) pentoxycarbonyl group, 6- (3-trifluoromethylphenyl) hexyloxycarbonyl group, 6- (4-trifluoromethylphenyl) hexyloxycarbonyl group, 6- (4-trifluoromethylphenyl) hexyloxycarbonyl group A trifluoromethoxyphenyl) hexyl oxycarbonyl group etc. can be mentioned.

  Phenyl C 2-6 alkenyl carbonyl group [in which at least a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C 1-6 alkyl group and a halogen substituted or unsubstituted C 1-6 alkoxy group on a phenyl ring As 1 type may be substituted, for example, 1 to 5 groups selected from an unsubstituted or halogen atom, a halogen C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group, It is preferably a group composed of a substituted or unsubstituted phenyl group and an alkenylcarbonyl group having 2 to 6 carbon atoms and 1 to 3 double bonds. The phenyl C2-6 alkenyl carbonyl group includes both trans and cis forms. As such a phenyl C2-6 alkenyl carbonyl group, for example, 2-phenyl vinyl carbonyl group, 3-phenyl-2-propenyl carbonyl group (conventional name: cinnamoyl group), 4-phenyl-2-butenyl carbonyl group, 4-phenyl-3-butenylcarbonyl group, 4-phenyl-1,3-butadienylcarbonyl group, 5-phenyl-1,3,5-hexatrienylcarbonyl group, 3- (2-fluorophenyl)- 2-propenyl carbonyl group, 3- (3-fluorophenyl) -2-propenyl carbonyl group, 3- (4-fluorophenyl) -2-propenyl carbonyl group, 3- (2,3-difluorophenyl) -2-propenyl group Carbonyl group, 3- (2,3,4,5,6-pentafluorophenyl) -2-propenylcarbonyl group 3- (2,4-difluorophenyl) -2-propenylcarbonyl group, 3- (3,4-difluorophenyl) -2-propenylcarbonyl group, 3- (3,5-difluorophenyl) -2-propenylcarbonyl group 3- (2-chlorophenyl) -2-propenylcarbonyl group, 3- (3-chlorophenyl) -2-propenylcarbonyl group, 3- (4-chlorophenyl) -2-propenylcarbonyl group, 3- (2,3- (2-chlorophenyl) -2-propenylcarbonyl group) Dichlorophenyl) -2-propenylcarbonyl group, 3- (2,4-dichlorophenyl) -2-propenylcarbonyl group, 3- (3,4-dichlorophenyl) -2-propenylcarbonyl group, 3- (3,5-dichlorophenyl) group -2-propenyl carbonyl group, 3- (2-bromophenyl) -2-propenyl carbonyl group, -(3-bromophenyl) -2-propenylcarbonyl group, 3- (4-bromophenyl) -2-propenylcarbonyl group, 3- (2-methylphenyl) -2-propenylcarbonyl group, 3- (3-methyl Phenyl) -2-propenylcarbonyl group, 3- (4-methylphenyl) -2-propenylcarbonyl group, 3- (4-trifluoromethylphenyl) -2-propenylcarbonyl group, 3- (2-fluoro-4- 4 Bromophenyl) -2-propenylcarbonyl group, 3- (4-chloro-3-fluorophenyl) -2-propenylcarbonyl group, 3- (2,3,4-trichlorophenyl) -2-propenylcarbonyl group, 3- (2,4,6-trichlorophenyl) -2-propenylcarbonyl group, 3- (4-isopropylphenyl) -2-prope Nylcarbonyl group, 3- (4-n-butylphenyl) -2-propenylcarbonyl group, 3- (2,4-dimethylphenyl) -2-propenylcarbonyl group, 3- (2,3-dimethylphenyl) -2 -Propenylcarbonyl group, 3- (2,6-dimethylphenyl) -2-propenylcarbonyl group, 3- (3,5-dimethylphenyl) -2-propenylcarbonyl group, 3- (2,5-dimethylphenyl)- 2-propenyl carbonyl group, 3- (2,4,6-trimethylphenyl) -2-propenyl carbonyl group, 3- (3,5-ditrifluoromethylphenyl) -2-propenyl carbonyl group, 3- (4-n) -Butoxyphenyl) -2-propenylcarbonyl group, 3- (2,4-dimethoxyphenyl) -2-propenylcarbonyl group, 3- (2, 2, 3- -Dimethoxyphenyl) -2-propenylcarbonyl group, 3- (2,6-dimethoxyphenyl) -2-propenylcarbonyl group, 3- (3,5-dimethoxyphenyl) -2-propenylcarbonyl group, 3- (2, 2, 3-dimethoxyphenyl) 5-dimethoxyphenyl) -2-propenylcarbonyl group, 3- (3,5-ditrifluoromethoxyphenyl) -2-propenylcarbonyl group, 3- (3-chloro-4-methoxyphenyl) -2-propenylcarbonyl group, 3- (2-chloro-4-trifluoromethoxyphenyl) -2-propenylcarbonyl group, 3- (3-methyl-4-fluorophenyl) -2-propenylcarbonyl group, 3- (4-bromo-3-triol) Fluoromethylphenyl) -2-propenylcarbonyl group, 3- (3-trifluoromethylphenyl) -2 Propenyl carbonyl group, 3- (4-trifluoromethylphenyl) -2-propenyl carbonyl group, 3- (2-trifluoromethoxyphenyl) -2-propenyl carbonyl group, 3- (3-trifluoromethoxyphenyl) -2 -Propenylcarbonyl group, 3- (4-trifluoromethoxyphenyl) -2-propenylcarbonyl group, 3- (2-methoxyphenyl) -2-propenylcarbonyl group, 3- (3-methoxyphenyl) -2-propenylcarbonyl Group, 3- (4-methoxyphenyl) -2-propenylcarbonyl group, 3- (3,4-dimethoxyphenyl) -2-propenylcarbonyl group, 3- (3,5-dimethoxyphenyl) -2-propenylcarbonyl group , 4- (4-chlorophenyl) -2-butenylcarbonyl group, 4- (4 -Chlorophenyl) -3-butenylcarbonyl group, 5- (4-chlorophenyl) -2-pentenylcarbonyl group, 5- (4-chlorophenyl) -4-pentenylcarbonyl group, 5- (4-chlorophenyl) -3-pentenyl group Group, 6- (4-chlorophenyl) -5-hexenylcarbonyl group, 6- (4-chlorophenyl) -4-hexenyl group, 6- (4-chlorophenyl) -3-hexenylcarbonyl group, 6- (4-chlorophenyl) group A -3-hexenyl carbonyl group etc. can be mentioned.

  As C1-4 alkylenedioxy group, a methylene dioxy group, ethylene dioxy group, trimethylene dioxy group, tetramethylene dioxy group etc. can be illustrated, for example.

  Examples of the amino-substituted sulfonyl group which may have a C1-6 alkyl group as a substituent include an aminosulfonyl group, a methylaminosulfonyl group, an ethylaminosulfonyl group, a propylaminosulfonyl group, an isopropylaminosulfonyl group, a butylaminosulfonyl group, tert-Butylaminosulfonyl group, pentylaminosulfonyl group, hexylaminosulfonyl group, dimethylaminosulfonyl group, diethylaminosulfonyl group, dipropylaminosulfonyl group, dibutylaminosulfonyl group, dipentylaminosulfonyl group, dihexylaminosulfonyl group, N-methyl -N-ethylaminosulfonyl group, N-ethyl-N-propylaminosulfonyl group, N-methyl-N-butylaminosulfonyl group, N-methyl-N-hexylamide It can be exemplified aminosulfonyl group which may have one or two a C1~6 alkyl group as a substituent such as a sulfonyl group.

  As the phenyl C1-6 alkoxy group, for example, benzyloxy group, 2-phenylethoxy group, 1-phenylethoxy group, 3-phenylpropoxy group, 2-phenylpropoxy group, 4-phenylbutoxy group, 5-phenylpentoxy group , 4-phenylpentoxy group, 6-phenylhexyloxy group, 2-methyl-3-phenylpropoxy group, 1,1-dimethyl-2-phenylethoxy group and the like.

  As a pyrrolidinyl group [at least one oxo group may be substituted on the pyrrolidine ring], for example, pyrrolidinyl group, 2-oxopyrrolidinyl group, 2,5-dioxopyrrolidinyl group, etc. And pyrrolidinyl groups (1 to 2 oxo groups may be substituted on the pyrrolidine ring) can be mentioned.

  As the pyrrolidinyl C1-6 alkoxy group, for example, (1-pyrrolidinyl) methoxy group, 2- (1-pyrrolidinyl) ethoxy group, 1- (2-pyrrolidinyl) ethoxy group, 3- (1-pyrrolidinyl) propoxy group, 2 -(3-pyrrolidinyl) propoxy group, 4- (1-pyrrolidinyl) butoxy group, 5- (2-pyrrolidinyl) pentoxy group, 4- (3-pyrrolidinyl) pentoxy group, 6- (1-pyrrolidinyl) hexyloxy group, Examples include 2-methyl-3- (1-pyrrolidinyl) propoxy group, 1,1-dimethyl-2- (1-pyrrolidinyl) ethoxy group and the like.

  As the benzofuryl C1-6 alkyl group (on the benzofuran ring, at least one halogen atom may be substituted as a substituent), for example, 2-benzofurylmethyl group, 1- (2-benzofuryl) ethyl Group, 2- (4-benzofuryl) ethyl group, 3- (5-benzofuryl) propyl group, 4- (6-benzofuryl) butyl group, 5- (7-benzofuryl) pentyl group, 6- (2-benzofuryl) hexyl Group, 4-fluoro-2-benzofurylmethyl group, 5-fluoro-2-benzofurylmethyl group, 6-fluoro-2-benzofurylmethyl group, 7-fluoro-2-benzofurylmethyl group, 4-chloro- 2-benzofurylmethyl, 5-chloro-2-benzofurylmethyl, 6-chloro-2-benzofurylmethyl, 7-chloro-2-benzo Rylmethyl group, 4-bromo-2-benzofurylmethyl group, 5-bromo-2-benzofurylmethyl group, 6-bromo-2-benzofurylmethyl group, 7-bromo-2-benzofurylmethyl group, 4-iodo -2-benzofurylmethyl group, 5-iodo-2-benzofurylmethyl group, 6-iodo-2-benzofurylmethyl group, 7-iodo-2-benzofurylmethyl group, 4-fluoro-3-benzofurylmethyl group Group, 5-fluoro-3-benzofurylmethyl group, 6-fluoro-3-benzofurylmethyl group, 7-fluoro-3-benzofurylmethyl group, 4-chloro-3-benzofurylmethyl group, 5-chloro- 3-benzofurylmethyl group, 6-chloro-3-benzofurylmethyl group, 7-chloro-3-benzofurylmethyl group, 4-bromo-3-benzofurylmethyl , 5-bromo-3-benzofurylmethyl group, 6-bromo-3-benzofurylmethyl group, 7-bromo-3-benzofurylmethyl group, 4-iodo-3-benzofurylmethyl group, 5-iodo-3 -Benzofurylmethyl group, 6-iodo-3-benzofurylmethyl group, 7-iodo-3-benzofurylmethyl group, 2- (4-fluoro-2-benzofuryl) ethyl group, 2- (5-fluoro-2) -Benzofuryl) ethyl group, 2- (6-fluoro-2-benzofuryl) ethyl group, 2- (7-fluoro-2-benzofuryl) ethyl group, 2- (4-chloro-2-benzofuryl) ethyl group, 2- (5-chloro-2-benzofuryl) ethyl group, 2- (6-chloro-2-benzofuryl) ethyl group, 2- (7-chloro-2-benzofuryl) ethyl group, 2- (4-fluoro-3) -Benzofuryl) methyl group, 2- (5-fluoro-3-benzofuryl) methyl group, 2- (6-fluoro-3-benzofuryl) ethyl group, 2- (7-fluoro-3-benzofuryl) ethyl group, 2- (4-chloro-3-benzofuryl) ethyl group, 2- (5-chloro-3-benzofuryl) ethyl group, 2- (6-chloro-3-benzofuryl) ethyl group, 2- (7-chloro-3-benzofuryl) ) Ethyl group, 2- (4-fluoro-2-benzofuryl) ethyl group, 6- (5-fluoro-2-benzofuryl) hexyl group, 6- (6-fluoro-2-benzofuryl) hexyl group, 6- (7) -Fluoro-2-benzofuryl) hexyl group, 6- (4-chloro-2-benzofuryl) hexyl group, 6- (5-chloro-2-benzofuryl) hexyl group, 6- (6-chloro-) -Benzofuryl) hexyl group, 6- (7-chloro-2-benzofuryl) hexyl group, 6- (4-fluoro-3-benzofuryl) methyl group, 6- (5-fluoro-3-benzofuryl) hexyl group, 6- (6-Fluoro-3-benzofuryl) hexyl group, 6- (7-fluoro-3-benzofuryl) hexyl group, 6- (4-chloro-3-benzofuryl) hexyl group, 6- (5-chloro-3-benzofuryl) ) Hexyl group, 6- (6-chloro-3-benzofuryl) hexyl group, 6- (7-chloro-3-benzofuryl) hexyl group, (2,4-dibromo-3-benzofuryl) methyl group, (4,5 Benzofuryl-substituted C1-6 alkyl group which may be substituted by 1 to 3 halogen atoms on the benzofuran ring such as 6,6-trichloro-3-benzofuryl) methyl group It can gel.

  A phenoxy C1-6 alkyl group (on the phenyl ring, at least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group, and a halogen-substituted or unsubstituted C1-6 alkoxy group; Is optionally substituted) is a group consisting of an unsubstituted phenoxy group or a halogen-substituted or unsubstituted C1-6 alkyl group as defined above, a halogen-substituted or unsubstituted C1-6 alkoxy group and a halogen And the selected group is a group composed of a phenoxy group substituted by 1 to 5, preferably 1 to 3 and a C1 to 6 alkyl group, and examples thereof include a phenoxymethyl group, a 2-phenoxyethyl group, and a 3-phenoxy group. Propyl, 4-phenoxybutyl, 5-phenoxypentyl, 6-phenoxyhexyl, 4-fluoro-6-methy Phenoxymethyl group, 2-fluoro-4-bromophenoxymethyl group, 2-fluoro-4-bromophenoxymethyl group, 4-chloro-3-fluorophenoxymethyl group, 2-chlorophenoxymethyl group, 3-chlorophenoxymethyl group 4-chlorophenoxymethyl group, 3,4-dichlorophenoxymethyl group, 2,3,4-trichlorophenoxymethyl group, 3,4,5-trichlorophenoxymethyl group, 2,4,6-trichlorophenoxymethyl group, 2- (2-chlorophenoxy) ethyl group, 2- (3-chlorophenoxy) ethyl group, 2- (4-chlorophenoxy) ethyl group, 2- (3,4-dichlorophenoxy) ethyl group, 2- (4 -Fluorophenoxy) ethyl group, 4-isopropylphenoxymethyl group, 4-n-butylphenoxy group Group, 4-methylphenoxymethyl group, 2-methylphenoxymethyl group, 3-methylphenoxymethyl group, 4-n-propylphenoxymethyl group, 4-isopropylphenoxymethyl group, 2,4-dimethylphenoxymethyl group, 2 , 3-Dimethylphenoxymethyl, 2,6-dimethylphenoxymethyl, 3,5-dimethylphenoxymethyl, 2,5-dimethylphenoxymethyl, 2,4,6-trimethylphenoxymethyl, 4-hexylphenoxy Methyl group, 2- (3-methylphenoxy) ethyl group, 2- (3,4-dimethylphenoxy) ethyl group, 3,5-ditrifluoromethylphenoxymethyl group, 2,3,4,5,6-pentafluoro Phenoxymethyl group, 4-isopropoxyphenoxymethyl group, 4-n-butoxypheno Xymethyl group, 4-methoxyphenoxymethyl group, 2-methoxyphenoxymethyl group, 3-methoxyphenoxymethyl group, 2- (3-methoxyphenoxy) ethyl group, 2- (4-methoxyphenoxy) ethyl group, 2- (3) , 4-Dimethoxyphenoxy) ethyl group, 2,4-dimethoxyphenoxymethyl group, 2,3-dimethoxyphenoxymethyl group, 3,4-dimethoxyphenoxymethyl group, 2,6-dimethoxyphenoxymethyl group, 3,5-dimethoxyme Phenoxymethyl group, 2,5-dimethoxyphenoxymethyl group, 2,4,6-trimethoxyphenoxymethyl group, 3,4,5-trimethoxyphenoxymethyl group, 3,5-ditrifluoromethoxyphenoxymethyl group, 2- Isopropoxyphenoxymethyl group, 3-chloro-4-methoxy group Noxymethyl group, 2-chloro-4-methoxyphenoxymethyl group, 2-chloro-4-trifluoromethoxyphenoxymethyl group, 3-methyl-4-fluorophenoxymethyl group, 4-bromo-3-trifluoromethylphenoxymethyl group 2- (4-fluorophenoxy) ethyl group, 3- (4-fluorophenoxy) propyl group, 4- (4-fluorophenoxy) butyl group, 5- (4-fluorophenoxy) pentyl group, 6- (4-fluorophenoxy) pentyl group Fluorophenoxy) hexyl group, 4-chlorophenoxymethyl group, 3- (4-chlorophenoxy) propyl group, 4- (4-chlorophenoxy) butyl group, 5- (4-chlorophenoxy) pentyl group, 6- (4) -Chlorophenoxy) hexyl group, 4-methylphenoxymethyl group, 2- (4-methylphenoxy) Ethyl group, 2- (2-isopropylphenoxy) ethyl group, 2- (4-isopropylphenoxy) ethyl group, 2- (4-hexylphenoxy) ethyl group, 2- (2-fluoro-5-methylphenoxy) ethyl group , 2- (2-chloro-4-methoxyphenoxy) ethyl group, 2- (3-fluoro-4-chlorophenoxy) ethyl group, 2- (3,4,5-trimethylphenoxy) ethyl group, 3- (4 -Methylphenoxy) propyl group, 4- (4-methylphenoxy) butyl group, 5- (4-methylphenoxy) pentyl group, 6- (4-methylphenoxy) hexyl group, 4-trifluoromethylphenoxymethyl group, 2 -Trifluoromethylphenoxymethyl group, 3-trifluoromethylphenoxymethyl group, 2- (4-trifluoromethylphenoxy) group ) Ethyl group, 2- (2-trifluoromethylphenoxy) ethyl group, 2- (3-trifluoromethylphenoxy) ethyl group, 3- (4-trifluoromethylphenoxy) propyl group, 4- (4-trifluoro) Methylphenoxy) butyl group, 5- (4-trifluoromethylphenoxy) pentyl group, 6- (4-trifluoromethylphenoxy) hexyl group, 4-trifluoromethoxyphenoxymethyl group, 2- (4-trifluoromethoxyphenoxy group ) Ethyl group, 2- (3-trifluoromethoxyphenoxy) ethyl group, 2- (2-trifluoromethoxyphenoxy) ethyl group, 3- (4-trifluoromethoxyphenoxy) propyl group, 4- (4-trifluoro) Methoxyphenoxy) butyl group, 5- (4-trifluoromethoxyphenoxy) Nthyl group, 6- (4-trifluoromethoxyphenoxy) hexyl group, 4-methoxyphenoxymethyl group, 2-isopropoxyphenoxymethyl group, 2- (4-methoxyphenoxy) ethyl group, 3- (4-methoxyphenoxy) group A propyl group, 4- (4-methoxy phenoxy) butyl group, 5- (4-methoxy phenoxy) pentyl group, 6- (4- methoxy phenoxy) hexyl group etc. can be mentioned.

  A thiazolyl C1-6 alkyl group (on the thiazolyl ring at least one phenyl group [on the phenyl ring a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy Group) may be substituted), for example, 2-thiazolylmethyl group, 4-thiazolylmethyl group, 5-thiazolylmethyl group, 5) -Phenyl-4-thiazolylmethyl group, 4-phenyl-5-thiazolylmethyl group, 2-phenyl-4-thiazolylmethyl group, 2-phenyl-5-thiazolylmethyl group, 2,5-diphenyl-4-thiazolylmethyl group, 2,4- Diphenyl-5-thiazolylmethyl group, 5- (2-fluorophenyl) -4-thiazolyl group Group, 4- (2-fluorophenyl) -5-thiazolylmethyl group, 2- (2-chlorophenyl) -4-thiazolylmethyl group, 2- (2-bromophenyl) -5-thiazolylmethyl group, 2- (2,3 , 4,5,6-pentafluorophenyl) -4-thiazolylmethyl group, 2- (2-bromophenyl) -5-thiazolylmethyl group, 5- (3-iodophenyl) -4-thiazolylmethyl group, 4- (3- (3-iodophenyl) -4-thiazolylmethyl group Fluorophenyl) -5-thiazolylmethyl group, 2- (2,3-difluorophenyl) -4-thiazolylmethyl group, 2- (3-bromophenyl) -5-thiazolylmethyl group, 2- (3,4,5-trifluoro Phenyl) -4-thiazolylmethyl group, 2- (3-fluorophenyl) -5-thiazolylmethyl group, 5- (2,4,6-trichlorophenyl) ) -4-thiazolylmethyl group, 4- (2,3,4,5,6-pentafluorophenyl) -5-thiazolylmethyl group, 2- (4-fluorophenyl) -4-thiazolylmethyl group, 4- (2-fluoro) Phenyl) -5-thiazolylmethyl group, 2- (4-fluorophenyl) -5-thiazolylmethyl group, 5- (2-chlorophenyl) -4-thiazolylmethyl group, 4- (2-chlorophenyl) -5-thiazolylmethyl group, 2- (2-chlorophenyl) -5-thiazolylmethyl group, 5- (3-methylphenyl) -4-thiazolylmethyl group, 4- (3-ethylphenyl) -5-thiazolylmethyl group, 2- (3-propylphenyl) -4- 4 Thiazolylmethyl group, 2- (2-n-butylphenyl) -5-thiazolylmethyl group, 2- (3-n-pentylphenyl) group ) -4-thiazolylmethyl group, 2- (3-n-hexylphenyl) -5-thiazolylmethyl group, 5- (3,4-dimethylphenyl) -4-thiazolylmethyl group, 4- (2,4,6-trimethylphenyl group) 2) 5-thiazolyl methyl group, 2- (4-methoxyphenyl) -4-thiazolyl methyl group, 2- (4-ethoxyphenyl) -5-thiazolyl methyl group, 2- (4-propoxyphenyl) -4-thiazolyl methyl group, 2 -(4-n-butoxyphenyl) -5-thiazolylmethyl group, 2- (2-thiazolyl) ethyl group, 2- (4-thiazolyl) ethyl group, 2- (5-thiazolyl) ethyl group, 2- [5- (2-n-Pentyloxyphenyl) -4-thiazolyl] ethyl group, 2- [2- (2-n-hexyloxyphenyl) -5-thiazolyl] ethyl , 2- [2- (2,5-dimethoxyphenyl) -4-thiazolyl] ethyl group, 2- [2- (2,4,6-trimethoxyphenyl) -5-thiazolyl] ethyl group, 2- (2 -Trifluoromethylphenyl) -4-thiazolylmethyl group, 2,4-di (trifluoromethyl) phenyl-5-thiazolylmethyl group, 2-trifluoromethoxyphenyl-4-thiazolylmethyl group, 2,3-di (trifluoromethoxy) group ) Phenyl-5-thiazolylmethyl group, 2- (2-methyl-5-trifluoromethoxyphenyl-4-thiazolyl) ethyl group, 3- (2-thiazolyl) propyl group, 2- (4-thiazolyl) propyl group, 3) -(5-thiazolyl) propyl group, 3-[(2-methoxy-4-trifluoromethylphenyl) -4-thiazolyl]] propyl group 4- (2-thiazolyl) butyl group, 4- (4-thiazolyl) butyl group, 3- (5-thiazolyl) butyl group, 4- [4- (2-chloro-4-methylphenyl) -2-thiazolyl] Butyl group, 5- (2-thiazolyl) pentyl group, 5- [5- (2-fluoro-3-methoxyphenyl) -2-thiazolyl] pentyl group, 5- (4-thiazolyl) pentyl group, 5- (5 Thiazolyl C.sub.1-6 alkyl groups such as thiazolyl) pentyl group, 5- (2-thiazolyl) hexyl group, 5- (4-thiazolyl) hexyl group, 5- (5-thiazolyl) hexyl group, 1-2 phenyl groups [on the phenyl ring, from the group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group 1 to 5 and preferably 1 to 3 groups may be substituted] may be substituted.

  The C1-6 alkoxycarbonyl group is a group composed of a C1-6 alkoxy group as defined above and a carbonyl group, and for example, a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, an isopropoxycarbonyl group, n-butoxycarbonyl group, isobutoxycarbonyl group, tert-butoxycarbonyl group, sec-butoxycarbonyl group, n-pentoxycarbonyl group, neopentoxy carbonyl group, n-hexyloxycarbonyl group, isohexyloxycarbonyl group, 3 -A methyl pentoxy carbonyl group etc. can be mentioned.

  A benzoyl group (in which at least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group is substituted on a phenyl ring; As benzoyl group, 2-fluorobenzoyl group, 3-fluorobenzoyl group, 4-fluorobenzoyl group, 2,3-difluorobenzoyl group, 3,4-difluorobenzoyl group, 2-chloro Benzoyl group, 3-chlorobenzoyl group, 4-chlorobenzoyl group, 2,3-dichlorobenzoyl group, 3,4-dichlorobenzoyl group, 2,4,6-trichlorobenzoyl group, 4-iodobenzoyl group, 2,3 , 4,5,6-pentafluorobenzoyl group, 2-bromobenzoyl group, 3-bromobenzoyl group 4-bromobenzoyl group, 2,3-dibromobenzoyl group, 3,4-dibromobenzoyl group, 2-methylbenzoyl group, 3-methylbenzoyl group, 4-methylbenzoyl group, 2,3-dimethylbenzoyl group, 3, 4-dimethylbenzoyl group, 3,4,5-trimethylbenzoyl group, 2-trifluoromethylbenzoyl group, 3-trifluoromethylbenzoyl group, 4-trifluoromethylbenzoyl group, 2,3-ditrifluoromethylbenzoyl group, 3,4-ditrifluoromethylbenzoyl group, 2-methoxybenzoyl group, 3-methoxybenzoyl group, 4-methoxybenzoyl group, 3,4-dimethoxybenzoyl group, 2,4,6-trimethoxybenzoyl group, 2-triyl Fluoromethoxybenzoyl group, 3-trifluoromethoxybenzoyl , 4-trifluoromethoxybenzoyl group, 2-methoxy-3-fluorobenzoyl group, 3-methyl-4-chlorobenzoyl, 3-trifluoromethoxy-4-methylbenzoyl group, 2-methoxy-4-trifluoromethylbenzoyl group Groups and the like (in the phenyl ring, a group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group, a halogen-substituted or unsubstituted C1-6 alkoxy group, and the like) And preferably 1 to 3 substituents may be mentioned.

  A phenylcarbamoyl group (in which at least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group is substituted on a phenyl ring And “optionally substituted” means a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group on the phenyl ring. An aniline which may be substituted, preferably 1 to 3 anilines, N-C1-6 alkyl aniline, or a group composed of N-phenyl C1-6 alkyl aniline and a carbonyl group, for example, a phenyl carbamoyl group , 2-fluorophenylcarbamoyl group, 3-fluorophenylcarbamoyl group, 4-fluorophenylcarbamoyl group , 2-chlorophenylcarbamoyl group, 3-chlorophenylcarbamoyl group, 4-chlorophenylcarbamoyl group, 2-bromophenylcarbamoyl group, 3-bromophenylcarbamoyl group, 4-bromophenylcarbamoyl group, 2-iodophenylcarbamoyl group, 3-iodo Phenylcarbamoyl group, 4-iodophenylcarbamoyl group, 2,3-difluorophenylcarbamoyl group, 3,4-difluorophenylcarbamoyl group, 3,5-difluorophenylcarbamoyl group, 2,4-difluorophenylcarbamoyl group, 2, 6 -Difluorophenylcarbamoyl group, 2,3-dichlorophenylcarbamoyl group, 3,4-dichlorophenylcarbamoyl group, 3,5-dichlorophenylcarbamoyl group, 2,4-dichlorophenyl carboxyl group Bamoyl group, 2,6-dichlorophenylcarbamoyl group, 3,4,5-trifluorophenylcarbamoyl group, 2,3,4,5,6-pentafluorophenylcarbamoyl group, 3,4,5-trichlorophenylcarbamoyl group, 2,4,6-trifluorophenylcarbamoyl group, 2,4,6-trichlorophenylcarbamoyl group, 2-methylphenylcarbamoyl group, 3-methylphenylcarbamoyl group, 4-methylphenylcarbamoyl group, 2-methyl-3- Chlorophenylcarbamoyl group, 3-methyl-4-chlorophenylcarbamoyl group, 2-chloro-4-methylphenylcarbamoyl group, 2-methyl-3-fluorophenylcarbamoyl group, 2-trifluoromethylphenylcarbamoyl group, 3-trifluoromethyl Phenylcal Bamoyl group, N-methyl-N-phenylcarbamoyl group, N- (2-fluorophenyl) -N-methylcarbamoyl group, N- (3-fluorophenyl) -N-methylcarbamoyl group, N- (4-fluorophenyl) ) -N-methylcarbamoyl group, N- (2-chlorophenyl) -N-methylcarbamoyl group, N- (3-chlorophenyl) -N-methylcarbamoyl group, N- (4-chlorophenyl) -N-methylcarbamoyl group, N- (4-bromophenyl) -N-methylcarbamoyl group, N- (2-iodophenyl) -N-methylcarbamoyl group, N- (3-iodophenyl) -N-methylcarbamoyl group, N- (4-iodophenyl) Iodophenyl) -N-methylcarbamoyl group, N- (2,3-difluorophenyl) -N-methylcarbamoyl group, N- ( , 4-difluorophenyl) -N-methylcarbamoyl group, N- (3,5-difluorophenyl) -N-methylcarbamoyl group, N- (2,4-difluorophenyl) -N-methylcarbamoyl group, N- ( 2,6-Difluorophenyl) -N-methylcarbamoyl group, N- (2,3-dichlorophenyl) -N-methylcarbamoyl group, N- (3,4-dichlorophenyl) -N-methylcarbamoyl group, N- (3 5-dichlorophenyl) -N-methylcarbamoyl group, N- (2,4-dichlorophenyl) -N-methylcarbamoyl group, N- (2,6-dichlorophenyl) -N-methylcarbamoyl group, N- (3,4 3,5-Trifluorophenyl) -N-methylcarbamoyl group, N- (3,4,5-trichlorophenyl) -N-methylcarba Group, N- (2,4,6-trifluorophenyl) -N-methylcarbamoyl group, N- (2,4,6-trichlorophenyl) -N-methylcarbamoyl group, N- (2-methylphenyl) group -N-methylcarbamoyl group, N- (3-methylphenyl) -N-methylcarbamoyl group, N- (4-methylphenyl) -N-methylcarbamoyl group, N- (2-methyl-3-chlorophenyl) -N -Methylcarbamoyl group, N- (3-methyl-4-chlorophenyl) -N-methylcarbamoyl group, N- (2-chloro-4-methylphenyl) -N-methylcarbamoyl group, N- (2-methyl-3) -Fluorophenyl) -N-methylcarbamoyl group, N- (2-trifluoromethylphenyl) -N-methylcarbamoyl group, N- (4-trifluoromethylphenyl) Phenyl) -N-methylcarbamoyl group, N-benzyl-N-phenylcarbamoyl group, N-benzyl-N- (2-fluorophenyl) carbamoyl group, N-benzyl-N- (3-fluorophenyl) carbamoyl group, N -Benzyl-N- (4-fluorophenyl) carbamoyl group, N-benzyl-N- (2-chlorophenyl) carbamoyl group, N-benzyl-N- (3-chlorophenyl) carbamoyl group, N-benzyl-N- (4 -Chlorophenyl) carbamoyl group, N-benzyl-N- (2-bromophenyl) carbamoyl group, N-benzyl-N- (3-bromophenyl) carbamoyl group, N-benzyl-N- (4-bromophenyl) carbamoyl group , N-benzyl-N- (2-iodophenyl) carbamoyl group, N-benzyl-N- (3 Iodophenyl) carbamoyl group, N-benzyl-N- (4-iodophenyl) carbamoyl group, N-benzyl-N- (2,3-difluorophenyl) carbamoyl group, N-benzyl-N- (3,4-difluoro) Phenyl) carbamoyl group, N-benzyl-N- (3,5-difluorophenyl) carbamoyl group, N-benzyl-N- (2,4-difluorophenyl) carbamoyl group, N-benzyl-N- (2,6-) Difluorophenyl) carbamoyl group, N-benzyl-N- (2,3-dichlorophenyl) carbamoyl group, N-benzyl-N- (3,4-dichlorophenyl) carbamoyl group, N-benzyl-N- (3,5-dichlorophenyl) ) Carbamoyl group, N-benzyl-N- (2,4-dichlorophenyl) carbamoyl group, N-ben Group N- (2,6-dichlorophenyl) carbamoyl group, N-benzyl-N- (3,4,5-trifluorophenyl) carbamoyl group, N-benzyl-N- (3,4,5-trichlorophenyl) Carbamoyl group, N-benzyl-N- (2,4,6-trifluorophenyl) carbamoyl group, N-benzyl-N- (2,4,6-trichlorophenyl) carbamoyl group, N-benzyl-N- (2 -Methylphenyl) carbamoyl group, N-benzyl-N- (3-methylphenyl) carbamoyl group, N-benzyl-N- (4-methylphenyl) carbamoyl group, N-benzyl-N- (2-methyl-3-) Chlorophenyl) carbamoyl group, N-benzyl-N- (3-methyl-4-chlorophenyl) carbamoyl group, N-benzyl-N- (2-chloro-4) -Methylphenyl) carbamoyl group, N-benzyl-N- (2-methyl-3-fluorophenyl) carbamoyl group, N-benzyl-N- (2-trifluoromethylphenyl) carbamoyl group, N-benzyl-N- ( 3-trifluoromethylphenyl) carbamoyl group, N-benzyl-N- (4-trifluoromethylphenyl) carbamoyl group, 2-pentafluoroethylphenylcarbamoyl group, 3-pentafluoroethylphenylcarbamoyl group, 4-pentafluoroethyl Phenylcarbamoyl group, 2-isopropylphenylcarbamoyl group, 3-isopropylphenylcarbamoyl group, 4-isopropylphenylcarbamoyl group, 2-tert-butylphenylcarbamoyl group, 3-tert-butylphenylcarbamoyl group, 4-t rt-Butylphenylcarbamoyl group, 2-sec-butylphenylcarbamoyl group, 3-sec-butylphenylcarbamoyl group, 4-sec-butylphenylcarbamoyl group, 2-n-heptafluoropropylphenylcarbamoyl group, 3-n-hepta Fluoropropylphenylcarbamoyl group, 4-n-heptafluoropropylphenylcarbamoyl group, 4-pentylphenylcarbamoyl group, 4-hexylphenylcarbamoyl group, 2,4-dimethylphenylcarbamoyl group, 2,4,6-trimethylphenylcarbamoyl group , 3,4-dimethoxyphenylcarbamoyl group, 3,4,5-trimethoxyphenylcarbamoyl group, 2-methoxyphenylcarbamoyl group, 3-methoxyphenylcarbamoyl group, 4-methoxyphenyl Ruvamoyl group, 2-methoxy-3-chlorophenylcarbamoyl group, 2-fluoro-3-methoxyphenylcarbamoyl group, 2-fluoro-4-methoxyphenylcarbamoyl group, 2,6-dimethoxyphenylcarbamoyl group, 2,3,4- Trifluorophenylcarbamoyl group, 3,4,5-trifluorophenylcarbamoyl group, 2-trifluoromethoxyphenylcarbamoyl group, 3-trifluoromethoxyphenylcarbamoyl group, 4-trifluoromethoxyphenylcarbamoyl group, 2-pentafluoroethoxy Phenylcarbamoyl group, 3-pentafluoroethoxyphenylcarbamoyl group, 4-pentafluoroethoxyphenylcarbamoyl group, 2-isopropoxyphenylcarbamoyl group, 3-isopropoxyphenylcarbyl Bamoyl group, 4-isopropoxyphenylcarbamoyl group, 2-tert-butoxyphenylcarbamoyl group, 3-tert-butoxyphenylcarbamoyl group, 4-tert-butoxyphenylcarbamoyl group, 2-sec-butoxyphenylcarbamoyl group, 3-sec 4-butoxyphenylcarbamoyl group, 4-sec-butoxyphenylcarbamoyl group, 2-n-heptafluoropropoxyphenylcarbamoyl group, 3-n-heptafluoropropoxyphenylcarbamoyl group, 4-n-heptafluoropropoxyphenylcarbamoyl group, 4- Examples include n-pentyloxyphenylcarbamoyl group, 4-n-hexyloxyphenylcarbamoyl group and the like.

  Examples of the 4H-1,3-benzodioxynyl group (at least one halogen atom may be substituted on the 4H-1,3-benzodioxin ring) include, for example, (2-, 4- , 5-, 6-, 7- or 8-) 4H-1,3-benzodioxynyl group, 2,2,4,4-tetrafluoro- (5-, 6-, 7- or 8-) 4H 1,3-benzodioxynyl group, 2-chloro- (2-, 4-, 5-, 6-, 7- or 8-) 4H-1,3-benzodioxynyl group, 4-bromo- (2-, 4-, 5-, 6-, 7- or 8-) 4H-1,3-benzodioxynyl group, 2,4-dichloro- (2-, 4-, 5-, 6-, 7- or 8-) 4H-1,3-benzodioxinyl group 2,4,6-trifluoro- (2-, 4-, 5-, 7- or 8-) 4H-1,3-benzodi Examples thereof include 4H-1,3-benzodioxynyl groups such as an oxynyl group (1 to 4 halogen atoms may be substituted on the 4H-1,3-benzodioxin ring).

  Examples of the benzothiazolyl group (in which at least one C1-6 alkyl group may be substituted on the benzothiazole ring) include, for example, (2-, 4-, 5-, 6-, or 7-) benzothiazolyl Group, 2-methyl-5-benzothiazolyl group, 4-ethyl-6-benzothiazolyl group, 5-propyl-7-benzothiazolyl group, 6-tert-butyl-2-benzothiazolyl group, 7-pentyl-4-benzothiazolyl group, 2 Benzothiazolyl groups such as 4-hexyl-5-benzothiazolyl group, 2,4-dimethyl-5-benzothiazolyl group, 2,4,6-trimethyl-7-benzothiazolyl group (1 to 3 C1-6 on the benzothiazole ring And alkyl groups may be substituted).

As the 2,3-dihydro-1H-indenyl group (on the 2,3-dihydro-1H-indene ring, at least one oxo group may be substituted), for example, 2,3-dihydro- 2,3-dihydro-1H-indenyl groups such as 1H-indenyl group, 1-oxo-2,3-dihydro-1H-indenyl group, 1,3-dioxo-2,3-dihydro-1H-indenyl group And one or two oxo groups may be substituted on the 3-dihydro-1H-indan ring)
A phenyl C 2-6 alkenyl group (on the phenyl ring at least one of the groups selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group And 1 to 5 groups selected from unsubstituted or halogen atoms, halogen-substituted or unsubstituted C.sub.1-6 alkyl groups, and halogen-substituted or unsubstituted C.sub.1-6 alkoxy groups. It is preferably a group composed of 1 or 2 of 1 to 3 substituted phenyl groups and an alkenyl group having 2 to 6 carbon atoms and 1 to 3 double bonds. The phenyl C2-6 alkenyl group includes both trans and cis forms. As such a phenyl C2-6 alkenyl group, for example, 2-phenylvinyl group, 3-phenyl-2-propenyl group (conventional name: cinnamyl group), 3, 3-diphenyl-2-propenyl group, 3-phenyl -2-methyl-2-propenyl group, 4-phenyl-2-butenyl group, 4,4-diphenyl-2-butenyl group, 4-phenyl-3-butenyl group, 4-phenyl-1,3-butadienyl group, 5-phenyl-1,3,5-hexatrienyl group, 5,5-diphenyl-3-pentenyl group, 6,6-diphenyl-2-hexenyl group, 6-phenyl-1,3-hexadienyl group, 3- (2-fluorophenyl) -2-propenyl group, 3- (3-fluorophenyl) -2-propenyl group, 3- (4-fluorophenyl) -2-propenyl group, 3- (2, 2, 3 -Difluorophenyl) -2-propenyl group, 3- (2,3,4,5,6-pentafluorophenyl) -2-propenyl group, 3- (2,4-difluorophenyl) -2-propenyl group, 3 -(3,4-difluorophenyl) -2-propenyl group, 3- (3,5-difluorophenyl) -2-propenyl group, 3- (2-chlorophenyl) -2-propenyl group, 3- (3-chlorophenyl) ) -2-propenyl group, 3- (4-chlorophenyl) -2-propenyl group, 3- (2,3-dichlorophenyl) -2-propenyl group, 3- (2,4-dichlorophenyl) -2-propenyl group, 3- (3,4-dichlorophenyl) -2-propenyl group, 3- (3,5-dichlorophenyl) -2-propenyl group, 3- (2,6-dichlorophenyl) -2-prope group And 3- (3,6-dichlorophenyl) -2-propenyl group, 3- (3,5,6-trichlorophenyl) -2-propenyl group, 3- (2,4,5-trichlorophenyl) -2 -Propenyl group, 3- (2-bromophenyl) -2-propenyl group, 3- (3-bromophenyl) -2-propenyl group, 3- (4-bromophenyl) -2-propenyl group, 3- (2) -Methylphenyl) -2-propenyl group, 3- (3-methylphenyl) -2-propenyl group, 3- (4-methylphenyl) -2-propenyl group, 3- (2-trifluoromethylphenyl) -2 -Propenyl group, 3- (2-fluoro-4-bromophenyl) -2-propenyl group, 3- (4-chloro-3-fluorophenyl) -2-propenyl group, 3- (2,3,4-triphenyl group) Chlorophenyl) -2-propenyl group, 3- (2,4,6-trichlorophenyl) -2-propenyl group, 3- (4-ethylphenyl) -2-propenyl group, 3- (4-n-hexylphenyl) -2 -Propenyl group, 3- (4-isopropylphenyl) -2-propenyl group, 3- (4-n-butylphenyl) -2-propenyl group, 3- (2,4-dimethylphenyl) -2-propenyl group, 3- (2,3-dimethylphenyl) -2-propenyl group, 3- (2,6-dimethylphenyl) -2-propenyl group, 3- (3,5-dimethylphenyl) -2-propenyl group, 3- (2,5-dimethylphenyl) -2-propenyl group, 3- (2,4,6-trimethylphenyl) -2-propenyl group, 3- (3,5-ditrifluoromethylphenyl) -2-propenyl group, 3- ( -N-butoxyphenyl) -2-propenyl group, 3- (2,4-dimethoxyphenyl) -2-propenyl group, 3- (2,3-dimethoxyphenyl) -2-propenyl group, 3- (2, 6) -Dimethoxyphenyl) -2-propenyl group, 3- (3,5-dimethoxyphenyl) -2-propenyl group, 3- (2,5-dimethoxyphenyl) -2-propenyl group, 3- (3,5-ditriyl) Fluoromethoxyphenyl) -2-propenyl group, 3- (3-chloro-4-methoxyphenyl) -2-propenyl group, 3- (2-chloro-4-trifluoromethoxyphenyl) -2-propenyl group, 3- (3-methyl-4-fluorophenyl) -2-propenyl group, 3- (2-methyl-4-fluorophenyl) -2-propenyl group, 3- (3-trifluoromethyl-4) Fluorophenyl) -2-propenyl group, 3- (3-trifluoromethyl-2-fluorophenyl) -2-propenyl group, 3- (4-bromo-3-trifluoromethylphenyl) -2-propenyl group, 3 -(4-chloro-3-trifluoromethylphenyl) -2-propenyl group, 3- (3-trifluoromethylphenyl) -2-propenyl group, 3- (2-trifluoromethylphenyl) -2-propenyl group 3- (4-trifluoromethylphenyl) -2-propenyl group, 3- (2-trifluoromethoxyphenyl) -2-propenyl group, 3- (3-trifluoromethoxyphenyl) -2-propenyl group, 3 -(4-trifluoromethoxyphenyl) -2-propenyl group, 3- (2-methoxyphenyl) -2-propenyl group, 3- (3-metho) Xyphenyl) -2-propenyl group, 3- (4-methoxyphenyl) -2-propenyl group, 3- (4-n-hexyloxyphenyl) -2-propenyl group, 3- (3,4-dimethoxyphenyl)- 2-propenyl group, 3- (3,5-dimethoxyphenyl) -2-propenyl group, 4- (4-chlorophenyl) -2-butenyl group, 4- (4-chlorophenyl) -3-butenyl group, 5- ( 4-chlorophenyl) -2-pentenyl group, 5- (4-chlorophenyl) -4-pentenyl group, 5- (4-chlorophenyl) -3-pentenyl group, 6- (4-chlorophenyl) -5-hexenyl group, 6 -(4-chlorophenyl) -4-hexenyl group, 6- (4-chlorophenyl) -3-hexenyl group, 6- (4-chlorophenyl) -3-hexenyl group etc. Door can be.

  A phenyl group (on a phenyl ring, a C1-4 alkylenedioxy group, a cyano group, a nitro group, an amino group which may have a C1-6 alkyl group as a substituent, a C1-6 alkyl group as a substituent Amino substituted sulfonyl group, C1-6 alkoxycarbonyl group, C1-6 alkylthio group, phenoxy group, phenyl C1-6 alkoxy group, pyrrolidinyl group (on the pyrrolidine ring, at least one oxo group is substituted Imidazolyl group, isoxazolyl group, oxazolyl group, phenyl C1-6 alkyl group, phenyl group, amino C1-6 alkyl group which may have C1-6 alkyl group as a substituent, pyrrolidinyl C1-6 alkoxy group, Halogen atom, halogen-substituted or unsubstituted C1-6 alkyl group and halogen Or as at least one group selected from the group consisting of unsubstituted C.sub.1-6 alkoxy groups may be substituted, for example, a phenyl group (on the phenyl ring, a halogen atom, a halogen substituted or not substituted). 4-cyanophenyl group, in addition to at least one member selected from the group consisting of a substituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group; Cyanophenyl group, 2-cyanophenyl group, 3,4-dicyanophenyl group, 2,4,6-tricyanophenyl group, 4-nitrophenyl group, 3-nitrophenyl group, 2-nitrophenyl group, 3,4 -Dinitrophenyl group, 2,4,6-trinitrophenyl group, 4-dimethylaminophenyl group, 3-methylaminophenyl group, 2-N-ethyl-N-methyl ester 2-aminophenyl, 2,4-di (methylamino) phenyl, 2,4,6-tri (methylamino) phenyl, 4-dimethylaminosulfonylphenyl, 3-methylaminosulfonylphenyl, 2-N -Ethyl-N-methylaminosulfonylphenyl group, 2,4-di (methylaminosulfonyl) phenyl group, 2,4,6-tri (methylaminosulfonyl) phenyl group, 4-ethoxycarbonylphenyl group, 4-ethoxycarbonyl Phenyl, 3-methoxycarbonylphenyl, 2-propoxycarbonylphenyl, 2,4-diethoxycarbonylphenyl, 2,4,6-triethoxycarbonylphenyl, 4-methylthiophenyl, 3-ethylthiophenyl Group, 2-methylthiophenyl group, 3,4-dimethylthiophenyl group Group, 2,4,6-trimethylthiophenyl group, 3,4-ethylenedioxyphenyl group, 3,4-methylenedioxyphenyl group, 4-diisopropylaminomethylphenyl group, 3-methylaminomethylphenyl group, 2 -Ethylaminomethylphenyl group, 2,4-dimethylaminomethylphenyl group, 2,4,6-triethylaminomethylphenyl group, 4-phenoxyphenyl group, 3-phenoxyphenyl group, 2-phenoxyphenyl group, 2,4 -Diphenoxyphenyl group, 3,4,5-triphenoxyphenyl group, 4-benzyloxyphenyl group, 3-benzyloxyphenyl group, 2-benzyloxyphenyl group, 2,4-dibenzyloxyphenyl group, 2, 4,6-tribenzyloxyphenyl group, 4- (2-oxo-1-pyrrolidinyl) fe Group 4- (5-oxazolyl) phenyl group 4- (5-isoxazolyl) phenyl group 4- (1-imidazolyl) phenyl group 4-benzylphenyl group 3-benzylphenyl group 2-benzylphenyl group 3,4-dibenzylphenyl, 2,4,6-tribenzylphenyl, 4-biphenyl, 3-biphenyl, 2-biphenyl, 2,4-diphenylphenyl, 2,4,6- Phenyl such as triphenylphenyl group, 2- (2-imidazolyl) -4-phenoxyphenyl group, 3- (2-oxazolyl) -4-benzyloxyphenyl group, 4- (3-isoxazolyl) -2-benzylphenyl group, etc. Group (containing a C1-4 alkylenedioxy group, a cyano group, a nitro group and one or two C1-6 alkyl groups as a substituent on a phenyl ring Amino group, amino substituted sulfonyl group having 1 to 2 C1-6 alkyl groups as a substituent, C1-6 alkoxycarbonyl group, C1-6 alkylthio group, phenoxy group, phenyl C1-6 alkoxy group And pyrrolidinyl group (in pyrrolidine ring, at least one oxo group may be substituted), imidazolyl group, isoxazolyl group, oxazolyl group, phenyl C1-6 alkyl group, phenyl group, C1-6 as a substituent From the group consisting of an amino C1-6 alkyl group which may have an alkyl group, a pyrrolidinyl C1-6 alkoxy group, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group One to five, preferably one to three, of the selected groups may be substituted Can be mentioned.

  As a phenyl group [a halogen may be substituted on the phenyl ring], for example, a phenyl group, a 2-fluorophenyl group, a 3-fluorophenyl group, a 4-fluorophenyl group, a 2-chlorophenyl group, 3 -Chlorophenyl group, 4-chlorophenyl group, 2-bromophenyl group, 3-bromophenyl group, 4-bromophenyl group, 2-iodophenyl group, 3-iodophenyl group, 4-iodophenyl group, 2,3-difluoro Phenyl group, 3,4-difluorophenyl group, 3,5-difluorophenyl group, 2,4-difluorophenyl group, 2,6-difluorophenyl group, 2,3-dichlorophenyl group, 3,4-dichlorophenyl group, 3 5-dichlorophenyl group, 2,4-dichlorophenyl group, 2,6-dichlorophenyl group, 3,4,5-triyl Fluorophenyl group, 3,4,5-trichlorophenyl group, 2,4,6-trifluorophenyl group, 2,4,6-trichlorophenyl group, 2-fluoro-4-bromophenyl group, 4-chloro-3- Fluorophenyl group, 2,3,4-trichlorophenyl group, 3,4,5-trifluorophenyl group, 2,4,6-tribromophenyl group, 2,3,4,5,6-pentafluorophenyl group And a phenyl group which may be substituted by 1 to 5 halogen atoms on the phenyl ring thereof.

  Phenyl C1-6 alkoxy substituted C1-6 alkyl group (on the phenyl ring, C1-4 alkylenedioxy group, halogen atom, cyano group, phenyl group, phenyl C1-6 alkoxy group, phenyl C2-6 alkenyl group, phenoxy At least one group selected from the group consisting of a group, a C1-6 alkylthio group, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group may be substituted Are, for example, a phenyl C.sub.1-6 alkoxy substituted C.sub.1-6 alkyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group. In addition to at least one of the groups selected from the group consisting of Nylmethoxymethyl group, 3-cyanophenylmethoxymethyl group, 2-cyanophenylmethoxymethyl group, 2,4-dicyanophenylmethoxymethyl group, 2,4,6-tricyanophenylmethoxymethyl group, 4-biphenylmethoxymethyl group , 3-biphenyl methoxymethyl group, 2-biphenyl methoxymethyl group, 2,4-diphenylphenyl methoxymethyl group, 2,4,6-triphenylphenyl methoxymethyl group, 4-phenoxyphenyl methoxymethyl group, 3-phenoxyphenyl group Methoxymethyl group, 2-phenoxyphenyl methoxymethyl group, 3,4-diphenoxyphenyl methoxymethyl group, 3,4,5-triphenoxyphenyl methoxymethyl group, 4-methylthiophenyl methoxymethyl group, 3-ethylthiophenyl methoxy Me Group, 2-methylthiophenylmethoxymethyl group, 2,4-dimethylthiophenylmethoxymethyl group, 2,4,6-trimethylthiophenylmethoxymethyl group, 4-cyano-2-phenylphenylmethoxymethyl group, 3-phenoxy -4-methylthiophenyl methoxymethyl group, 3-trifluoromethyl-4-methylthiophenyl methoxymethyl group, 3-trifluoromethoxy-2-phenoxyphenyl methoxymethyl group, 3,4-methylenedioxyphenyl methoxymethyl group, 4 -Benzyloxyphenylmethoxymethyl group, 3,4-dibenzyloxyphenylmethoxymethyl group, 2,4,6-tribenzyloxyphenylmethoxymethyl group, 3-benzyloxyphenylmethoxymethyl group, 2-benzyloxyphenylmethoxymethyl group Group Phenyl such as 4-styrylphenyl methoxymethyl group, 3-styrylphenyl methoxymethyl group, 2-styrylphenyl methoxymethyl group, 2,4-distyrylphenyl methoxymethyl, 2,4,6-tristyrylphenyl methoxymethyl group C1-6 alkoxy substituted C1-6 alkyl group (in the phenyl ring, the alkyl moiety is a linear or branched alkylenedioxy group having 1 to 4 carbon atoms, a halogen atom, a cyano group, a phenyl group, an alkoxy moiety It is composed of a phenylalkoxy group which is a linear or branched alkoxy having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms and at least 1 to 2 double bonds, and includes both a trans form and a cis form Phenylalkenyl group, phenoxy group, linear or branched alkylthio group having 1 to 6 carbon atoms, halogen substitution Is a group selected from the group consisting of unsubstituted linear or branched alkyl groups having 1 to 6 carbon atoms and halogen substituted or unsubstituted linear or branched alkoxy groups having 1 to 6 carbon atoms One to five, preferably one to three, may be substituted (if the substituent is a C1 to 4 alkylenedioxy group, one to two may be substituted).

  A phenyl C1-6 alkoxy group (on the phenyl ring, a cyano group, a phenyl group, a C1-6 alkoxycarbonyl group, a phenoxy group, a C1-6 alkylthio group, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group, As at least one kind of group selected from the group consisting of halogen substituted or unsubstituted C1-6 alkoxy group may be substituted, for example, phenyl C1-6 alkoxy group (on the phenyl ring, halogen In addition to at least one of a group selected from the group consisting of an atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group; -Cyanophenyl methoxy group, 3-cyano benzyloxy group, 2-cyano benzyloxy group, 2,4-dicyano benzyl Xy, 2,3,4-tricyanobenzyloxy, 4-biphenylmethoxy, 3-biphenylmethoxy, 2-biphenylmethoxy, 2,4-diphenylbenzyloxy, 2,4,6-triphenyl Benzyloxy, 4-methoxycarbonylbenzyloxy, 3-ethoxycarbonylbenzyloxy, 2-methoxycarbonylbenzyloxy, 3,4-diethoxycarbonylbenzyloxy, 3,4,5-trimethoxycarbonylbenzyloxy Group, 3-phenoxybenzyloxy group, 2-phenoxybenzyloxy group, 4-phenoxybenzyloxy group, 2,4-diphenoxybenzyloxy group, 2,4,6-triphenoxybenzyloxy group, 4-methylthiobenzyloxy Group, 3-methylthiobenzyloxy group, -Methylthiobenzyloxy group, 3,4-dimethylthiobenzyloxy group, 2,5,6-trimethylthiobenzyloxy group, 3-cyano-4-bibenzyloxy group, 4-ethoxycarbonyl-3-phenoxybenzyloxy group , 3-methylthio-4-ethylbenzyloxy group, di (4-trifluoromethoxyphenyl) methoxy group, di (4-trifluoromethylphenyl) methoxy group, di (4-chlorophenyl) methoxy group, di (3-methoxy) group Phenyl) methoxy, di (2-methylphenyl) methoxy, di (2,4-dimethoxyphenyl) methoxy, di (3,4-dimethylphenyl) methoxy, di (2,4,6-trimethoxyphenyl) ) Methoxy group, di (3,4,5-trifluorophenyl) methoxy group, di (2,4,6-trifluo! Or C.sub.1-6 alkoxy group substituted with one or two phenyl groups such as orophenyl) methoxy group, 1- (4-trifluoromethoxyphenyl) -1- (2,4-dichlorophenyl) methoxy group, etc. A cyano group, a phenyl group, a C1-6 alkoxycarbonyl group, a phenoxy group, a C1-6 alkylthio group, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group 1 to 5, preferably 1 to 3 groups selected from the group may be substituted).

  Phenyl C 2-6 alkenyloxy group (on the phenyl ring, at least one of a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group 1 type may be substituted is 1 to 5 groups, preferably 1 to 5 groups selected from unsubstituted or halogen atoms, halogen C1-6 alkyl groups and halogen substituted or unsubstituted C1-6 alkoxy groups; It is a group composed of a substituted or unsubstituted phenyl group and an alkenyl group having 2 to 6 carbon atoms and at least 1 to 3 double bonds. The phenyl C2-6 alkenyloxy group includes both a trans form and a cis form. As such a phenyl C2-6 alkenyloxy group, for example, 2-phenylvinyloxy group, 3-phenyl-2-propenyloxy group (common name: cinnamyloxy group), 4-phenyl-2-butenyloxy group, 4-phenyl-3-butenyloxy group, 4-phenyl-1,3-butadienyloxy group, 5-phenyl-1,3,5-hexatrienyloxy group, 3- (2-fluorophenyl) -2- Propenyloxy group, 3- (3-fluorophenyl) -2-propenyloxy group, 3- (4-fluorophenyl) -2-propenyloxy group, 3- (2,3-difluorophenyl) -2-propenyloxy group , 3- (2,3,4,5,6-pentafluorophenyl) -2-propenyloxy group, 3- (2,4-difluorophenyl) -2-prop Nyloxy group, 3- (3,4-difluorophenyl) -2-propenyloxy group, 3- (3,5-difluorophenyl) -2-propenyloxy group, 3- (2-chlorophenyl) -2-propenyloxy group 3- (3-chlorophenyl) -2-propenyloxy group, 3- (4-chlorophenyl) -2-propenyloxy group, 3- (2,3-dichlorophenyl) -2-propenyloxy group, 3- (2, 2, 3-chlorophenyl) 4-dichlorophenyl) -2-propenyloxy group, 3- (3,4-dichlorophenyl) -2-propenyloxy group, 3- (3,5-dichlorophenyl) -2-propenyloxy group, 3- (2-bromophenyl) group ) -2-propenyloxy group, 3- (3-bromophenyl) -2-propenyloxy group, 3- (4-bromophenyl) -2-prope Roxy group, 3- (2-methylphenyl) -2-propenyloxy group, 3- (3-methylphenyl) -2-propenyloxy group, 3- (4-methylphenyl) -2-propenyloxy group, 3- (2-trifluoromethylphenyl) -2-propenyloxy group, 3- (2-fluoro-4-bromophenyl) -2-propenyloxy group, 3- (4-chloro-3-fluorophenyl) -2-propenyl group Oxy group, 3- (2,3,4-trichlorophenyl) -2-propenyloxy group, 3- (2,4,6-trichlorophenyl) -2-propenyloxy group, 3- (4-isopropylphenyl)- 2-propenyloxy group, 3- (4-n-butylphenyl) -2-propenyloxy group, 3- (2,4-dimethylphenyl) -2-propenyloxy group, 3 -(2,3-dimethylphenyl) -2-propenyloxy group, 3- (2,6-dimethylphenyl) -2-propenyloxy group, 3- (3,5-dimethylphenyl) -2-propenyloxy group, 3- (2,5-dimethylphenyl) -2-propenyloxy group, 3- (2,4,6-trimethylphenyl) -2-propenyloxy group, 3- (3,5-ditrifluoromethylphenyl) -2 -Propenyloxy group, 3- (4-n-butoxyphenyl) -2-propenyloxy group, 3- (2,4-dimethoxyphenyl) -2-propenyloxy group, 3- (2,3-dimethoxyphenyl)- 2-propenyloxy group, 3- (2,6-dimethoxyphenyl) -2-propenyloxy group, 3- (3,5-dimethoxyphenyl) -2-propenyloxy group, 3- 2,5-Dimethoxyphenyl) -2-propenyloxy group, 3- (3,5-ditrifluoromethoxyphenyl) -2-propenyloxy group, 3- (3-chloro-4-methoxyphenyl) -2-propenyloxy Group, 3- (2-chloro-4-trifluoromethoxyphenyl) -2-propenyloxy group, 3- (3-methyl-4-fluorophenyl) -2-propenyloxy group, 3- (4-bromo-3) -Trifluoromethylphenyl) -2-propenyloxy group, 3- (3-trifluoromethylphenyl) -2-propenyloxy group, 3- (4-trifluoromethylphenyl) -2-propenyloxy group, 3- ( 2-trifluoromethoxyphenyl) -2-propenyloxy group, 3- (3-trifluoromethoxyphenyl) -2-propenyl group And 3- (4-trifluoromethoxyphenyl) -2-propenyloxy, 3- (2-methoxyphenyl) -2-propenyloxy, 3- (3-methoxyphenyl) -2-propenyloxy, 3- (4-methoxyphenyl) -2-propenyloxy group, 3- (3,4-dimethoxyphenyl) -2-propenyloxy group, 3- (3,5-dimethoxyphenyl) -2-propenyloxy group, 4 -(4-chlorophenyl) -2-butenyloxy group, 4- (4-chlorophenyl) -3-butenyloxy group, 5- (4-chlorophenyl) -2-pentenyloxy group, 5- (4-chlorophenyl) -4-pentenyl group Oxy group, 5- (4-chlorophenyl) -3-pentenyloxy group, 6- (4-chlorophenyl) -5-hexenyloxy group, 6- Examples include (4-chlorophenyl) -4-hexenyloxy group, 6- (4-chlorophenyl) -3-hexenyloxy group, 6- (4-chlorophenyl) -3-hexenyloxy group and the like.

  As a C1 to C6 alkyl group which may have a hydroxyl group as a substituent, in addition to the C1 to C6 alkyl group, a hydroxymethyl group, a 2-hydroxyethyl group, a 1-hydroxyethyl group, a 3-hydroxypropyl group, 2 , 3-Dihydroxypropyl group, 4-hydroxybutyl group, 3,4-dihydroxybutyl group, 1,1-dimethyl-2-hydroxyethyl group, 5-hydroxypentyl group, 6-hydroxyhexyl group, 2-methyl-3 -C1-6 linear or branched alkyl group which may have 1 to 3 hydroxyl groups, such as-hydroxypropyl group and 2,3,4- trihydroxy butyl group, can be mentioned.

  The C1-6 alkanoyl group is a group derived from an aliphatic carboxylic acid having 1 to 6 carbon atoms, and examples thereof include a formyl group, an acetyl group, a propionyl group, a butyryl group, a pentanoyl group, and a hexanoyl group. Etc.

  Phenyl C1-6 alkoxycarbonyl group [in which at least a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group on a phenyl ring And 1 type may be substituted] is selected from the group consisting of a halogen atom as defined above, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group A group consisting of a phenyl C1-6 alkoxy group optionally substituted with 1 to 5, preferably 1 to 3 alkoxy groups and a carbonyl group, and examples thereof include a benzyloxycarbonyl group and a 2-phenylethoxycarbonyl group , 3-phenylpropoxycarbonyl group, 2-phenylpropoxycarbonyl group, 4-phenylbutoxy cal Group, 5-phenylpentoxy carbonyl group, 4-phenyl pentoxy carbonyl group, 6-phenylhexyloxycarbonyl group, 2-fluorobenzyloxycarbonyl group, 3-fluorobenzyloxycarbonyl group, 4-fluorobenzyloxycarbonyl group , 2- (2-fluorophenyl) ethoxycarbonyl group, 2- (3-fluorophenyl) ethoxycarbonyl group, 2- (4-fluorophenyl) ethoxycarbonyl group, 2-chlorobenzyloxycarbonyl group, 3-chlorobenzyloxy Carbonyl group, 4-chlorobenzyloxycarbonyl group, 2-fluoro-4-bromobenzyloxycarbonyl group, 4-chloro-3-fluorobenzyloxycarbonyl group, 2,3,4-trichlorobenzyloxycarbonyl group, 3,4 5-trifluorobenzyloxycarbonyl group, 2,3,4,5,6-pentafluorobenzyloxycarbonyl group, 2,4,6-trichlorobenzyloxycarbonyl group, 4-isopropylbenzyloxycarbonyl group, 4-n- Butyl benzyloxycarbonyl group, 4-methylbenzyloxycarbonyl group, 2-methylbenzyloxycarbonyl group, 3-methylbenzyloxycarbonyl group, 2,4-dimethylbenzyloxycarbonyl group, 2,3-dimethylbenzyloxycarbonyl group, 2,6-Dimethylbenzyloxycarbonyl group, 3,5-dimethylbenzyloxycarbonyl group, 2,5-dimethylbenzyloxycarbonyl group, 2,4,6-trimethylbenzyloxycarbonyl group, 3,5-ditrifluoromethylbenzyl group Oki A carbonyl group, 4-isopropoxybenzyloxycarbonyl group, 4-n-butoxybenzyloxycarbonyl group, 4-methoxybenzyloxycarbonyl group, 2-methoxybenzyloxycarbonyl group, 3-methoxybenzyloxycarbonyl group, 2,4 -Dimethoxybenzyloxycarbonyl group, 2,3-dimethoxybenzyloxycarbonyl group, 2,6-dimethoxybenzyloxycarbonyl group, 3,5-dimethoxybenzyloxycarbonyl group, 2,5-dimethoxybenzyloxycarbonyl group, 2,4 , 6-trimethoxybenzyloxycarbonyl group, 3,5-ditrifluoromethoxybenzyloxycarbonyl group, 2-isopropoxybenzyloxycarbonyl group, 3-chloro-4-methoxybenzyloxycarbonyl group, 2 Chloro-4-trifluoromethoxybenzyloxycarbonyl group, 3-methyl-4-fluorobenzyloxycarbonyl group, 4-bromo-3-trifluoromethylbenzyloxycarbonyl group, 2- (2-chlorophenyl) ethoxycarbonyl group, 2 -(3-chlorophenyl) ethoxycarbonyl group, 2- (4-chlorophenyl) ethoxycarbonyl group, 2-trifluoromethylbenzyloxycarbonyl group, 3-trifluoromethylbenzyloxycarbonyl group, 4-trifluoromethylbenzyloxycarbonyl group , 2-trifluoromethoxybenzyloxy carbonyl group, 3-trifluoromethoxybenzyloxycarbonyl group, 4-trifluoromethoxybenzyloxycarbonyl group, 2- (2-trifluoromethylphenyl) etho A carbonyl group, 2- (3-trifluoromethylphenyl) ethoxycarbonyl group, 2- (4-trifluoromethylphenyl) ethoxycarbonyl group, 2- (2-trifluoromethoxyphenyl) ethoxycarbonyl group, 2- (3 -Trifluoromethoxyphenyl) ethoxycarbonyl group, 2- (4-trifluoromethoxyphenyl) ethoxycarbonyl group, 3- (2-trifluoromethylphenyl) propoxycarbonyl group, 3- (3-trifluoromethylphenyl) propoxycarbonyl group Group, 3- (4-trifluoromethylphenyl) propoxycarbonyl group, 3- (2-trifluoromethylphenyl) propoxycarbonyl group, 3- (3-trifluoromethoxyphenyl) propoxycarbonyl group, 3- (4-trichloromethoxyphenyl) propoxycarbonyl group Fluoro methoxy group Phenyl) propoxycarbonyl group, 4- (3-trifluoromethylphenyl) butoxycarbonyl group, 5- (4-trifluoromethylphenyl) pentoxy carbonyl group, 4- (4-trifluoromethylphenyl) pentoxy carbonyl group, 4- (4-trifluoromethoxyphenyl) pentoxycarbonyl group, 6- (3-trifluoromethylphenyl) hexyloxycarbonyl group, 6- (4-trifluoromethylphenyl) hexyloxycarbonyl group, 6- (4-trifluoromethylphenyl) hexyloxycarbonyl group A trifluoromethoxyphenyl) hexyl oxycarbonyl group etc. can be mentioned.

  Examples of the amino group which may have a group selected from the group consisting of a C1-6 alkanoyl group and a C1-6 alkyl group as a substituent include, for example, an amino group, a methylamino group, an ethylamino group and an n-propylamino group , Isopropylamino group, n-butylamino group, tert-butylamino group, n-pentylamino group, n-hexylamino group, dimethylamino group, diethylamino group, di-n-propylamino group, di-n-butylamino group Group, di-n-pentylamino group, di-n-hexylamino group, N-methyl-N-ethylamino group, N-ethyl-N-n-propylamino group, N-methyl-N-n-butylamino Group, N-methyl-Nn-hexylamino group, N-methyl-N-acetylamino group, acetylamino group, formylamino group, n-propioni C1-6 alkanoyl group and C1-6 as a substituent such as amino group, n-butyrylamino group, isobutyrylamino group, n-pentanoylamino group, n-hexanoylamino group, N-ethyl-N-acetylamino group and the like Mention may be made of an amino group which may have one or two groups selected from the group consisting of 6 alkyl groups.

  Examples of the 1,2,3,4-tetrahydroquinolyl group (in the 1,2,3,4-tetrahydroquinoline ring, at least one oxo group may be substituted as a substituent) include, for example, 1 1,2,3,4-tetrahydro-1-quinolyl group, 1,2,3,4-tetrahydro-2-quinolyl group, 1,2,3,4-tetrahydro-3-quinolyl group, 1,2,3,3, 4-tetrahydro-4-quinolyl group, 1,2,3,4-tetrahydro-5-quinolyl group, 1,2,3,4-tetrahydro-6-quinolyl group, 1,2,3,4-tetrahydro-7 -Quinolyl group, 1,2,3,4-tetrahydro-8-quinolyl group, 2-oxo-1,2,3,4-tetrahydro-1-quinolyl group, 4-oxo-1,2,3,4- Tetrahydro-1-quinolyl group, 2,4-dioxo-1, 3,4-tetrahydro-1-quinolyl group, 2-oxo-1,2,3,4-tetrahydro-6-quinolyl group, 2-oxo-1,2,3,4-tetrahydro-4-quinolyl group, 2-oxo-1,2,3,4-tetrahydro-7-quinolyl group, 2-oxo-1,2,3,4-tetrahydro-8-quinolyl group, 2-oxo-1,2,3,4- 1,2,3,4-Tetrahydroquinolyl groups such as tetrahydro-5-quinolyl group, 2-oxo-1,2,3,4-tetrahydro-3-quinolyl group (1,2,3,4-tetrahydroquinoline On the ring, one or two oxo groups may be substituted as a substituent).

  The C1-6 alkylsulfonyl group is a group composed of an alkyl group having 1 to 6 carbon atoms and a sulfonyl group, and examples thereof include a methanesulfonyl group, an ethanesulfonyl group, an n-propanesulfonyl group, and n group. And -butanesulfonyl group, n-pentanesulfonyl group, n-hexanesulfonyl group and the like can be mentioned.

  The C3-8 cycloalkyl group is a 3-, 8-, 5-, 6-, 7-, or 8-membered cyclic alkyl group having 3 to 8 carbon atoms. For example, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, 3,4-dimethylcyclopentyl group, 3,3-dimethylcyclohexyl group and the like can be mentioned.

  The C1-6 alkylthio group is a linear or branched alkylthio group having 1 to 6 carbon atoms, and examples thereof include a methylthio group, an ethylthio group, an n-propylthio group, an isopropylthio group, n -Butylthio, isobutylthio, tert-butylthio, sec-butylthio, n-pentylthio, neopentylthio, n-hexylthio, isohexylthio, 3-methylpentylthio and the like. .

  A phenylsulfonyl group (on the phenyl ring, at least one of a group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group, a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group, and As the optionally substituted phenyl group, it is composed of an unsubstituted phenylsulfonyl group, the halogen atom as defined above, a halogen substituted or unsubstituted C1-6 alkyl group, a halogen substituted or unsubstituted C1-6 alkoxy group and A phenylsulfonyl group having 1 to 5, preferably 1 to 3 substituents selected from the group consisting of, for example, phenylsulfonyl group, 2-fluorophenylsulfonyl group, 3-fluorophenylsulfonyl group, 4-fluoro Phenylsulfonyl group, 2-chlorophenylsulfonyl group, 3-chlorophenyl sulfone Group, 4-chlorophenylsulfonyl group, 2-bromophenylsulfonyl group, 3-bromophenylsulfonyl group, 4-bromophenylsulfonyl group, 2-iodophenylsulfonyl group, 3-iodophenylsulfonyl group, 4-iodophenylsulfonyl group, 2,3-Difluorophenylsulfonyl group, 3,4-difluorophenylsulfonyl group, 3,5-difluorophenylsulfonyl group, 2,4-difluorophenylsulfonyl group, 2,6-difluorophenylsulfonyl group, 2,3-dichlorophenyl group A sulfonyl group, 3,4-dichlorophenylsulfonyl group, 3,5-dichlorophenylsulfonyl group, 2,4-dichlorophenylsulfonyl group, 2,6-dichlorophenylsulfonyl group, 3,4,5-trifluorophenylsulfonyl group, , 4,5-trichlorophenylsulfonyl group, 2,4,6-trifluorophenylsulfonyl group, 2,4,6-trichlorophenylsulfonyl group, 2-fluoro-4-bromophenylsulfonyl group, 4-chloro-3- Fluorophenylsulfonyl group, 2,3,4-trichlorophenylsulfonyl group, 3,4,5-trifluorophenylsulfonyl group, 2,3,4,5,6-pentafluorophenylsulfonyl group, 2,4,6- Trimethylphenylsulfonyl group, 4-n-butylphenylsulfonyl group, 2,4-dimethylphenylsulfonyl group, 2,3-dimethylphenylsulfonyl group, 2,6-dimethylphenylsulfonyl group, 3,5-dimethylphenylsulfonyl group, 2,5-Dimethylphenylsulfonyl group, 3,5-ditrifluoromethyl group Rphenylsulfonyl group, 4-n-butoxyphenylsulfonyl group, 2,4-dimethoxyphenylsulfonyl group, 2,3-dimethoxyphenylsulfonyl group, 2,6-dimethoxyphenylsulfonyl group, 3,5-dimethoxyphenylsulfonyl group, 2,5-Dimethoxyphenylsulfonyl group, 2,4,6-trimethoxyphenylsulfonyl group, 3,5-ditrifluoromethoxyphenylsulfonyl group, 3-chloro-4-methoxyphenylsulfonyl group, 2-chloro-4-triphenyl group Fluoromethoxyphenylsulfonyl group, 3-methyl-4-fluorophenylsulfonyl group, 4-bromo-3-trifluoromethylphenylsulfonyl group, 2-methylphenylsulfonyl group, 3-methylphenylsulfonyl group, 4-methylphenylsulfonyl group , 2- Tyl-3-chlorophenylsulfonyl group, 3-methyl-4-chlorophenylsulfonyl group, 2-chloro-4-methylphenylsulfonyl group, 2-methyl-3-fluorophenylsulfonyl group, 2-trifluoromethylphenylsulfonyl group, 3 -Trifluoromethylphenylsulfonyl group, 4-trifluoromethylphenylsulfonyl group, 2-pentafluoroethylphenylsulfonyl group, 3-pentafluoroethylphenylsulfonyl group, 4-pentafluoroethylphenylsulfonyl group, 2-isopropylphenylsulfonyl group , 3-isopropylphenylsulfonyl group, 4-isopropylphenylsulfonyl group, 2-tert-butylphenylsulfonyl group, 3-tert-butylphenylsulfonyl group, 4-tert-butylphene -Sulfonyl group, 2-sec-butylphenylsulfonyl group, 3-sec-butylphenylsulfonyl group, 4-sec-butylphenylsulfonyl group, 2-n-heptafluoropropylphenylsulfonyl group, 3-n-heptafluoropropylphenyl Sulfonyl group, 4-n-heptafluoropropylphenylsulfonyl group, 4-n-pentylphenylsulfonyl group, 4-n-hexylphenylsulfonyl group, 2-methoxyphenylsulfonyl group, 3-methoxyphenylsulfonyl group, 4-methoxyphenyl Sulfonyl group, 3-chloro-2-methoxyphenylsulfonyl group, 2-fluoro-3-methoxyphenylsulfonyl group, 2-fluoro-4-methoxyphenylsulfonyl group, 2,6-dimethoxyphenylsulfonyl group, 2,3,4 -To Trifluorophenylsulfonyl group, 2,4,6-trifluorophenylsulfonyl group, 2-trifluoromethoxyphenylsulfonyl group, 3-trifluoromethoxyphenylsulfonyl group, 4-trifluoromethoxyphenylsulfonyl group, 3-fluoro-2 -Trifluoromethoxyphenylsulfonyl group, 2-fluoro-3-trifluoromethoxyphenylsulfonyl group, 3-fluoro-4-trifluoromethoxyphenylsulfonyl group, 3-chloro-2-trifluoromethoxyphenylsulfonyl group, 2-chloro -3-trifluoromethoxyphenylsulfonyl group, 3-chloro-4-trifluoromethoxyphenylsulfonyl group, 2-pentafluoroethoxyphenylsulfonyl group, 3-pentafluoroethoxyphenylsulfonyl group, -Pentafluoroethoxyphenylsulfonyl group, 3-chloro-2-pentafluoroethoxyphenylsulfonyl group, 2-chloro-3-pentafluoroethoxyphenylsulfonyl group, 3-chloro-4-pentafluoroethoxyphenylsulfonyl group, 2-iso Propoxyphenylsulfonyl group, 3-isopropoxyphenylsulfonyl group, 4-isopropoxyphenylsulfonyl group, 2-tert-butoxyphenylsulfonyl group, 3-tert-butoxyphenylsulfonyl group, 4-tert-butoxyphenylsulfonyl group, 2- sec-butoxyphenylsulfonyl group, 3-sec-butoxyphenylsulfonyl group, 4-sec-butoxyphenylsulfonyl group, 2-n-heptafluoropropoxyphenylsulfonyl group, 3-n Heptafluoropropoxy phenylsulfonyl group, 4-n-heptafluoropropoxy phenylsulfonyl group, 4-n-pentoxy phenylsulfonyl group, and a 4-n-hexyloxy phenylsulfonyl group.

  Examples of the amino group-substituted C1-6 alkoxy group which may have a C1-6 alkyl group as a substituent include, for example, aminomethoxy group, 2-aminoethoxy group, 1-aminoethoxy group, 3-aminopropoxy group, 4- Aminobutoxy, 5-aminopentyloxy, 6-aminohexyloxy, 2-methyl-3-aminopropoxy, 1,1-dimethyl-2-aminoethoxy, ethylaminomethoxy, 1- (propylamino) ) Ethoxy, 2- (methylamino) ethoxy, 3- (isopropylamino) propoxy, 4- (n-butylamino) butoxy, 5- (n-pentylamino) pentyloxy, 6- (n-) Hexylamino) hexyloxy group, dimethylaminomethoxy group, 3-dimethylaminopropoxy group, (N-ethyl-N Examples of amino-C1-6 alkoxy group which may have one or two C1-6 alkyl groups as a substituent such as propylamino) methoxy group and 2- (N-methyl-N-hexylamino) ethoxy group it can.

  Phenyl group [on the phenyl ring, a halogen atom as a substituent, a halogen-substituted or unsubstituted C1-6 alkyl group, a halogen-substituted or unsubstituted C1-6 alkoxy group, a C1-6 alkanoyl group as a substituent, and Amino group which may have a group selected from the group consisting of 6 alkyl groups, C1-6 alkoxycarbonyl group, phenyl group, phenoxy group (on the phenyl ring, a halogen atom, halogen substituted or unsubstituted C1-6 At least one group selected from the group consisting of an alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted), an aminosulfonyl group, 1,2,3,4-tetrahydroquinolyl Group (on the 1,2,3,4-tetrahydroquinoline ring, at least one oxo group may be substituted as a substituent), C1 6 alkylsulfonyl group, C3-8 cycloalkyl group, nitro group, cyano group, C1-6 alkylthio group, phenylsulfonyl group (on the phenyl ring, halogen atom, halogen substituted or unsubstituted C1-6 alkyl group and halogen At least one of a group selected from the group consisting of a substituted or unsubstituted C1-6 alkoxy group may be substituted), a hydroxyl group-substituted C1-6 alkyl group and a group

(W ₁ represents a C 1-6 alkylene group, and R ^{11 ′} and R ^{12 ′} are the same or different and represent a C 1-6 alkoxy group.) At least one of the groups selected from the group consisting of As the above-mentioned halogen atom, halogen-substituted or unsubstituted C1-6 alkyl group, halogen-substituted or unsubstituted C1-6 alkoxy group, C1-6 alkanoyl group as a substituent and C1-6 alkyl Group having one or two groups selected from the group consisting of an amino group, a C1-6 alkoxycarbonyl group, a phenyl group, a phenoxy group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1 -5, preferably 1 to 3 groups selected from the group consisting of a -6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group), aminosulfo Group, 1,2,3,4-tetrahydroquinolyl group (1 to 2 oxo groups may be substituted as a substituent on the 1,2,3,4-tetrahydroquinoline ring), C1 To 6 alkylsulfonyl group, C3-8 cycloalkyl group, nitro group, cyano group, C1-6 alkylthio group, phenylsulfonyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and 1 to 5, preferably 1 to 3 groups selected from the group consisting of halogen substituted or unsubstituted C1 to 6 alkoxy groups may be substituted), hydroxyl group substituted C1 to 6 alkyl groups and groups

(In the formula, W ₁ represents a C 1 to C 6 alkylene group, and R ^{11 ′} and R ^{12 ′} are the same or different and each represents a C 1 to C 6 alkoxy group); Examples thereof include a phenyl group which may be substituted at 1 to 6, preferably 1 to 3 at the 2 to 6 position.

  As a hydroxy-substituted C1-6 alkyl group, for example, a hydroxymethyl group, a 2-hydroxyethyl group, a 1-hydroxyethyl group, a 3-hydroxypropyl group, a 2,3-dihydroxypropyl group, a 4-hydroxybutyl group, 3, 3, 4-dihydroxybutyl group, 1,1-dimethyl-2-hydroxyethyl group, 5-hydroxypentyl group, 6-hydroxyhexyl group, 2-methyl-3-hydroxypropyl group, 2,3,4-trihydroxybutyl group And C.sub.1-6 linear or branched alkyl groups having 1 to 3 hydroxyl groups.

  Examples of the halogen-substituted or unsubstituted C1-10 alkoxy group include, in addition to the halogen-substituted or unsubstituted C1-6 alkoxy group, a heptyloxy group, an octyloxy group, a nonyloxy group, a decyloxy group, and a 7-fluoroheptyloxy group. Group, 7,7,6-trifluoroheptyloxy group, 7,7,7,6,6,5,5-heptafluoroheptyloxy group, 8-chlorooctyloxy group, 8,8-dibromooctyloxy group, 6,7,8-trifluorooctyloxy group, 8,8,8,7,7,6,6- heptafluorooctyloxy group, 8,8,8,7,7-pentachlorooctyloxy group, 9 -Iodononyloxy group, 9,9-dibromononyloxy group, 9,9,9,8,8-pentachlorononyloxy group 9,9,9,8,8,7,7- 10-10 10 10 9 10 9 10 9 10 9 10 9 10 9 10 9 10 9 10 9 10 9 10 9 10 9 10 9 10 9 10 9 10 9 10 9 10 9 10 9 10 9 10 9 10 9 10 9 10 9 10 9 10 9 10 9 10 9 10 9 10 9 10 9 10 9 10 Examples include C1-10 alkoxy groups such as 8-heptafluorodecyloxy group, and C1-10 alkoxy groups substituted with 1 to 7 halogen atoms.

  Phenyl C 1-6 alkyl group (as a substituent, a C 1-4 alkylenedioxy group, a phenyl group, a halogen atom, a halogen substituted or unsubstituted C 1-6 alkyl group and a halogen substituted or unsubstituted C 1 At least one of a group selected from the group consisting of 6 alkoxy groups may be substituted) with an unsubstituted phenyl C.sub.1-6 alkyl group and a C.sub.1-4 alkyl group on the phenyl ring constituting those groups. 1 to 5 groups, preferably 1 group selected from the group consisting of a dioxy group, a phenyl group, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group A group which is substituted by 3 (in the case where the substituent is a C1 to 4 alkylenedioxy group, 1 to 2 may be substituted), and, for example, Nidyl group, 1-phenethyl group, 2-phenethyl group, 3-phenylpropyl group, 2-phenylpropyl group, 4-phenylbutyl group, 5-phenylpentyl group, 4-phenylpentyl group, 6-phenylhexyl group, 2 , 3-methylenedioxybenzyl group, 3,4-methylenedioxybenzyl group, 3-phenylbenzyl group, 2-phenylbenzyl group, 4-phenylbenzyl group, 3,4-diphenylbenzyl group, 2,4,6 -Triphenylbenzyl group, 2-fluorobenzyl group, 3-fluorobenzyl group, 4-fluorobenzyl group, 2-chlorobenzyl group, 3-chlorobenzyl group, 4-chlorobenzyl group, 2-bromobenzyl group, 3- Bromobenzyl group, 4-bromobenzyl group, 2-iodobenzyl group, 3-iodobenzyl group, 4-iodobenzyl , 2,3-difluorobenzyl group, 3,4-difluorobenzyl group, 3,5-difluorobenzyl group, 2,4-difluorobenzyl group, 2,6-difluorobenzyl group, 2,3-dichlorobenzyl group, 3 , 4-Dichlorobenzyl group, 3,5-dichlorobenzyl group, 2,4-dichlorobenzyl group, 2,6-dichlorobenzyl group, 2-fluoro-4-bromobenzyl group, 4-chloro-3-fluorobenzyl group 2,3,4-Trichlorobenzyl, 3,4,5-trifluorobenzyl, 2,4,6-trichlorobenzyl, 4-ethylbenzyl, 4-sec-butylbenzyl, 4-isopropylbenzyl Group, 4-n-butylbenzyl group, 4-methylbenzyl group, 2-methylbenzyl group, 3-methylbenzyl group, 2,4-dimethylbenzyl group 2,3-Dimethylbenzyl, 2,6-dimethylbenzyl, 3,5-dimethylbenzyl, 2,5-dimethylbenzyl, 2,4,6-trimethylbenzyl, 3,5-ditrifluoromethyl Benzyl group, 2,3,4,5,6-pentafluorobenzyl group, 4-isopropoxybenzyl group, 4-n-butoxybenzyl group, 4-tert-butoxybenzyl group, 4-methoxybenzyl group, 2-methoxy Benzyl group, 3-methoxybenzyl group, 2,4-dimethoxybenzyl group, 2,3-dimethoxybenzyl group, 2,6-dimethoxybenzyl group, 3,5-dimethoxybenzyl group, 2,5-dimethoxybenzyl group, 2 , 4,6-trimethoxybenzyl group, 3,5-ditrifluoromethoxybenzyl group, 2-isopropoxybenzyl group, 3-chloro 4-methoxybenzyl group, 2-chloro-4-trifluoromethoxybenzyl group, 3-methyl-4-fluorobenzyl group, 4-bromo-3-trifluoromethylbenzyl group, 2-trifluoromethylbenzyl group, 3- Trifluoromethylbenzyl group, 4-trifluoromethylbenzyl group, 2-pentafluoroethyl benzyl group, 3-pentafluoroethyl benzyl group, 4-pentafluoroethyl benzyl group, 2-trifluoromethoxybenzyl group, 3-trifluoro Methoxybenzyl group, 4-trifluoromethoxybenzyl group, 2-pentafluoroethoxybenzyl group, 3-pentafluoroethoxybenzyl group, 4-pentafluoroethoxybenzyl group, 2- (2-trifluoromethylphenyl) ethyl group, 2 -(3-trifluoromethyl group -Yl) ethyl group, 2- (4-trifluoromethylphenyl) ethyl group, 2- (2-trifluoromethoxyphenyl) ethyl group, 1- (3-trifluoromethoxyphenyl) ethyl group, 2- (4-trimethyl) Fluoromethoxyphenyl) ethyl group, 2- (2-pentafluoroethoxyphenyl) ethyl group, 2- (3-pentafluoroethoxyphenyl) ethyl group, 2- (4-pentafluoroethoxyphenyl) ethyl group, 3- (2 -Trifluoromethylphenyl) propyl group, 3- (3-trifluoromethylphenyl) propyl group, 3- (4-trifluoromethylphenyl) propyl group, 3- (2-trifluoromethoxyphenyl) propyl group, 3- (3-trifluoromethoxyphenyl) propyl group, 3- (4-trifluoromethoxyphenyl) group Ropyl group, 3- (3-pentafluoroethoxyphenyl) propyl group, 3- (4-pentafluoroethoxyphenyl) propyl group, 4- (3-pentafluoroethoxyphenyl) butyl group, 5- (4-trifluoromethyl) Phenyl) pentyl group, 4- (4-trifluoromethylphenyl) pentyl group, 4- (4-trifluoromethoxyphenyl) pentyl group, 6- (3-trifluoromethylphenyl) hexyl group, 6- (4- tri Examples include fluoromethylphenyl) hexyl group, 6- (4-trifluoromethoxyphenyl) hexyl group, 4- (4-chlorophenyl) butyl group and the like.

Phenyl C1-6 alkyl group [in the phenyl ring, a C1-4 alkylenedioxy group as a substituent, a phenyl group (in the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted Or at least one group selected from the group consisting of unsubstituted C1-6 alkoxy groups may be substituted), a group -N ( ^{R11A '} ) ^R12A' ( ^{R11A '} and ^R12A' is R ^{11A ′} and R ^{12A ′} , together with adjacent nitrogen atoms, are bonded to each other via or without nitrogen atoms, oxygen atoms or sulfur atoms May form a 5- to 7-membered saturated heterocyclic ring), a phenoxy group (on the phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted group. At least one group selected from the group consisting of 1 to 6 alkoxy groups may be substituted), phenyl C 1 to 6 alkoxy groups, amino group substituted C 1 which may have a C 1 to 6 alkyl group as a substituent -6 alkoxy group, a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group, and at least one group selected from the group consisting of a halogen-substituted or unsubstituted C1-10 alkoxy group may be substituted As a phenyl C1-6 alkyl group (in the phenyl ring, a C1 to 4 alkylenedioxy group as a substituent, a phenyl group, a halogen atom, a halogen substituted or unsubstituted C1 to 6 alkyl group and a halogen substituted); Or 4- (4-) in addition to at least one of a group selected from the group consisting of unsubstituted C1-6 alkoxy groups may be substituted Trifluoromethylphenyl) benzyl group, 4- (4-trifluoromethoxyphenyl) benzyl group, 4- (4-chlorophenyl) benzyl group, 4- (4-trifluoromethylphenoxy) benzyl group, 4- (4-trichlorophenyl) benzyl group Fluoromethoxyphenoxy) benzyl group, 4- (4-chlorophenoxy) benzyl group, 4-phenoxybenzyl group, 3-phenoxybenzyl group, 2-phenoxybenzyl group, 2,4-diphenoxybenzyl group, 2,4,6 -Triphenoxybenzyl group, 4-benzyloxybenzyl group, 3-benzyloxybenzyl group, 2-benzyloxybenzyl group, 3,4-dibenzyloxybenzyl group, 3,4,5-tribenzyloxybenzyl group, 4 -Octyloxybenzyl group, 3-nonyloxybenzyl group, 2-decyloxy Heptyl group, 4-heptyloxybenzyl group, 2,4-dioctyloxybenzyl group, 3,4,6-trioctyloxybenzyl group, 4- (8,8,8-trifluorooctyloxy) benzyl group, 4- 4- Dimethylaminobenzyl group, 4-diphenylaminobenzyl group, 4- (3-dimethylaminopropoxy) benzyl group, 4-di-n-butylaminobenzyl group, 3- (N-methyl-N-ethylamino) benzyl group, 2- (N-methyl-N-phenylamino) benzyl group, 2,4,6-methylaminobenzyl group, 3- (3-dimethylaminopropoxy) benzyl group, 2,4-di-n-butylaminobenzyl group , 4- (2-methylaminoethoxy) benzyl group, 2- (4-methylaminobutoxy) benzyl group, 4- (2-dimethylaminoethoxy) Benzyl, 2,3-diethylaminomethoxybenzyl, 2,4,6-tri (2-dimethylaminoethoxy) benzyl, 2-phenoxy-3-phenylbenzyl, 4-octyloxy-3-trifluoromethoxybenzyl Phenyl C1-6 alkyl groups such as 4-benzyloxy-2-dimethylaminobenzyl, 4- (1-pyrrolidinyl) benzyl, 4- (1-piperidyl) benzyl, etc. [as a substituent on a phenyl ring C 1-4 alkylenedioxy group, phenyl group (on the phenyl ring, a halogen atom, halogen-substituted or unsubstituted linear or branched alkyl group having 1 to 6 carbon atoms, halogen-substituted or unsubstituted carbon One to five, preferably one to three, groups selected from the group consisting of linear or branched alkoxy groups having 1 to 6 may be substituted. Group, —N (R ^{11A ′} ) R ^{12A ′} (R ^{11A ′} and R ^{12A ′} are the same or different and each represents a hydrogen atom, a C1-6 alkyl group or a phenyl group. R ^{11A ′} and R ^{12A ′} may be bonded to each other to form a 5- to 7-membered saturated heterocyclic ring together with adjacent nitrogen atoms, with or without a nitrogen atom, an oxygen atom or a sulfur atom) Group (on the phenyl ring, a halogen atom, a halogen-substituted or unsubstituted linear or branched alkyl group having 1 to 6 carbon atoms, a halogen-substituted or unsubstituted linear chain having 1 to 6 carbon atoms or 1 to 5, preferably 1 to 3 groups selected from the group consisting of branched alkoxy groups may be substituted, phenyl C1-6 alkoxy group, C1-6 alkyl group as a substituent A group selected from the group consisting of an amino group-substituted C1-6 alkoxy group which may have, a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-10 alkoxy group is 5 pieces, Preferably, 1 to 3 may be substituted. When the substituent is a C1-4 alkylenedioxy group, one to two substituents may be preferable.

  Benzofuryl C1-6 alkyl group [in the benzofuran ring, at least one of the groups selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group The species may be substituted], for example, (2-, 3-, 4-, 5-, 6- or 7-) benzofurylmethyl group, 1- (2-benzofuryl) ethyl group, 2- (3-benzofuryl) ethyl group, 3- (4-benzofuryl) propyl group, 2- (5-benzofuryl) propyl group, 2- (6-benzofuryl) propyl group, 4- (7-benzofuryl) butyl group, 5- (2-benzofuryl) pentyl group, 4- (3-benzofuryl) pentyl group, 6- (4-benzofuryl) hexyl group, 2-methyl-3- (5-benzofuryl) propyl group, 1,1-Dimethyl-2- (6-benzofuryl) ethyl group, (5-chloro-2-benzofuryl) methyl group, 2- (5-trifluoromethoxybenzofuryl) methyl group, 2- (5-trifluoromethyl benzo) Furyl) methyl group, (6-trifluoromethylbenzofuryl) methyl group, 2- (5-methylbenzofuryl) methyl group, 2- (5-methoxybenzofuryl) methyl group, (5,6-dibromo-2-) Benzofuryl) methyl group, (3,5,6-trifluoro-2-benzofuryl) methyl group, 2- (5,6-dimethylbenzofuryl) methyl group, 2- (5,7-dimethoxybenzofuryl) methyl group, 2- (5,6,7-trimethylbenzofuryl) methyl group, 2- (3,5,6-trimethoxybenzofuryl) methyl group, 2- (5-trifluoromethyl-6) Benzofuryl C1-6 alkyl groups such as chlorobenzofuryl) methyl group, 2- (5-trifluoromethoxy-6-methoxybenzofuryl) methyl group [on a benzofuran ring, halogen atoms, halogen substituted or unsubstituted C1 1 to 3 groups selected from the group consisting of 6 alkyl groups and halogen-substituted or unsubstituted C1-6 alkoxy groups may be substituted.

  A phenylsulfonyl group [on the phenyl ring, selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group, a halogen-substituted or unsubstituted C1-6 alkoxy group and a C1-4 alkylenedioxy group At least one kind of the above-mentioned groups may be substituted] with an unsubstituted phenylsulfonyl group, a halogen atom as defined above, a halogen substituted or unsubstituted C1-6 alkyl group, a halogen substituted or unsubstituted C1 A phenylsulfonyl group having 1 to 5, preferably 1 to 3 substituents selected from the group consisting of to 6 alkoxy groups and C1 to 4 alkylenedioxy groups (when the substituent is a C1 to 4 alkylenedioxy group Is preferably substituted by 1 to 2), for example, phenylsulfonyl, 2-fluorophenylsulfonyl , 3-fluorophenylsulfonyl group, 4-fluorophenylsulfonyl group, 2-chlorophenylsulfonyl group, 3-chlorophenylsulfonyl group, 4-chlorophenylsulfonyl group, 2-bromophenylsulfonyl group, 3-bromophenylsulfonyl group, 4-bromo Phenylsulfonyl group, 2-iodophenylsulfonyl group, 3-iodophenylsulfonyl group, 4-iodophenylsulfonyl group, 2,3-difluorophenylsulfonyl group, 3,4-difluorophenylsulfonyl group, 3,5-difluorophenylsulfonyl group Group, 2,4-difluorophenylsulfonyl group, 2,6-difluorophenylsulfonyl group, 2,3-dichlorophenylsulfonyl group, 3,4-dichlorophenylsulfonyl group, 3,5-dichlorophenyl sulfone Group, 2,4-dichlorophenylsulfonyl group, 2,6-dichlorophenylsulfonyl group, 3,4,5-trifluorophenylsulfonyl group, 3,4,5-trichlorophenylsulfonyl group, 2,4,6-trifluoro Phenylsulfonyl group, 2,4,6-trichlorophenylsulfonyl group, 2-fluoro-4-bromophenylsulfonyl group, 4-chloro-3-fluorophenylsulfonyl group, 2,3,4-trichlorophenylsulfonyl group, 3, 4,5-Trifluorophenylsulfonyl group, 2,3,4,5,6-pentafluorophenylsulfonyl group, 2,4,6-trimethylphenylsulfonyl group, 4-n-butylphenylsulfonyl group, 2,4- Dimethylphenylsulfonyl group, 2,3-dimethylphenylsulfonyl group, 2,6-di Methylphenylsulfonyl group, 3,5-dimethylphenylsulfonyl group, 2,5-dimethylphenylsulfonyl group, 3,5-ditrifluoromethylphenylsulfonyl group, 4-n-butoxyphenylsulfonyl group, 2,4-dimethoxyphenylsulfonyl group Group, 2,3-dimethoxyphenylsulfonyl group, 2,6-dimethoxyphenylsulfonyl group, 3,5-dimethoxyphenylsulfonyl group, 2,5-dimethoxyphenylsulfonyl group, 2,4,6-trimethoxyphenylsulfonyl group, 3,5-ditrifluoromethoxyphenylsulfonyl group, 3-chloro-4-methoxyphenylsulfonyl group, 2-chloro-4-trifluoromethoxyphenylsulfonyl group, 3-methyl-4-fluorophenylsulfonyl group, 4-bromo- 3- trifluoro Methylphenylsulfonyl group, 2-methylphenylsulfonyl group, 3-methylphenylsulfonyl group, 4-methylphenylsulfonyl group, 2-methyl-3-chlorophenylsulfonyl group, 3-methyl-4-chlorophenylsulfonyl group, 2-chloro- 4-methylphenylsulfonyl group, 2-methyl-3-fluorophenylsulfonyl group, 2-trifluoromethylphenylsulfonyl group, 3-trifluoromethylphenylsulfonyl group, 4-trifluoromethylphenylsulfonyl group, 2-pentafluoroethyl Phenylsulfonyl group, 3-pentafluoroethylphenylsulfonyl group, 4-pentafluoroethylphenylsulfonyl group, 2-isopropylphenylsulfonyl group, 3-isopropylphenylsulfonyl group, 4-isopropyl Henylsulfonyl group, 2-tert-butylphenylsulfonyl group, 3-tert-butylphenylsulfonyl group, 4-tert-butylphenylsulfonyl group, 2-sec-butylphenylsulfonyl group, 3-sec-butylphenylsulfonyl group, 4 -Sec-butylphenylsulfonyl group, 2-n-heptafluoropropylphenylsulfonyl group, 3-n-heptafluoropropylphenylsulfonyl group, 4-n-heptafluoropropylphenylsulfonyl group, 4-n-pentylphenylsulfonyl group, 4-n-hexylphenylsulfonyl group, 2-methoxyphenylsulfonyl group, 3-methoxyphenylsulfonyl group, 4-methoxyphenylsulfonyl group, 3-chloro-2-methoxyphenylsulfonyl group, 2-fluoro-3-methane Toxyphenylsulfonyl group, 2-fluoro-4-methoxyphenylsulfonyl group, 2,6-dimethoxyphenylsulfonyl group, 2,3,4-trifluorophenylsulfonyl group, 2,4,6-trifluorophenylsulfonyl group, 2 -Trifluoromethoxyphenylsulfonyl group, 3-trifluoromethoxyphenylsulfonyl group, 4-trifluoromethoxyphenylsulfonyl group, 3-fluoro-2-trifluoromethoxyphenylsulfonyl group, 2-fluoro-3-trifluoromethoxyphenylsulfonyl group Group, 3-fluoro-4-trifluoromethoxyphenylsulfonyl group, 3-chloro-2-trifluoromethoxyphenylsulfonyl group, 2-chloro-3-trifluoromethoxyphenylsulfonyl group, 3-chloro-4-trifluro group Lomethoxyphenylsulfonyl group, 2-pentafluoroethoxyphenylsulfonyl group, 3-pentafluoroethoxyphenylsulfonyl group, 4-pentafluoroethoxyphenylsulfonyl group, 3-chloro-2-pentafluoroethoxyphenylsulfonyl group, 2-chloro- 3-pentafluoroethoxyphenylsulfonyl group, 3-chloro-4-pentafluoroethoxyphenylsulfonyl group, 2-isopropoxyphenylsulfonyl group, 3-isopropoxyphenylsulfonyl group, 4-isopropoxyphenylsulfonyl group, 2-tert- Butoxyphenylsulfonyl group, 3-tert-butoxyphenylsulfonyl group, 4-tert-butoxyphenylsulfonyl group, 2-sec-butoxyphenylsulfonyl group, 3-sec-bu Xyphenylsulfonyl group, 4-sec-butoxyphenylsulfonyl group, 2-n-heptafluoropropoxyphenylsulfonyl group, 3-n-heptafluoropropoxyphenylsulfonyl group, 4-n-heptafluoropropoxyphenylsulfonyl group, 4-n -A pentoxy phenyl sulfonyl group, 4-n-hexyl oxyphenyl sulfonyl group, a 2, 3- methylene di oxy phenyl sulfonyl group, a 3, 4- methylene di oxy phenyl sulfonyl group etc. can be mentioned.

  Phenoxycarbonyl group [in the phenyl ring, at least one of a group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group is substituted May be, for example, phenoxycarbonyl group, 2-fluorophenoxycarbonyl group, 3-fluorophenoxycarbonyl group, 2,3,4,5,6-pentafluorophenoxycarbonyl group, 4-fluorophenoxycarbonyl group , 2-chlorophenoxycarbonyl group, 3-chlorophenoxycarbonyl group, 4-chlorophenoxycarbonyl group, 2,3-dichlorophenoxycarbonyl group, 3,4-dichlorophenoxycarbonyl group, 3,5-dichlorophenoxycarbonyl group, 2 -Bromophenoxycal Group, 3-bromophenoxycarbonyl group, 4-bromophenoxycarbonyl group, 2-methylphenoxycarbonyl group, 3-methylphenoxycarbonyl group, 4-methylphenoxycarbonyl group, 2-ethylphenoxycarbonyl group, 3-ethylsiphenoxy Carbonyl group, 4-ethylphenoxycarbonyl group, 4-n-propylphenoxycarbonyl group, 4-tert-butylphenoxycarbonyl group, 4-n-butylphenoxycarbonyl group, 2,3-dimethylphenoxycarbonyl group, 3,4, 5-trimethylphenoxycarbonyl group, 4-n-pentylphenoxycarbonyl group, 4-n-hexylphenoxycarbonyl group, 2-fluoro-4-bromophenoxycarbonyl group, 4-chloro-3-fluorophenoxycarbonyl group 2,3,4-Trichlorophenoxycarbonyl group, 2,4,6-trichloropheninoxycarbonyl group, 4-isopropylphenoxycarbonyl group, 4-n-butylphenoxycarbonyl group, 2,4-dimethylphenoxycarbonyl group, 2 3, 3-dimethylphenoxycarbonyl group, 2,6-dimethylphenoxycarbonyl group, 3,5-dimethylphenoxycarbonyl group, 2,5-dimethylphenoxycarbonyl group, 2,4,6-trimethylphenoxycarbonyl group, 3,5- Ditrifluoromethylphenoxycarbonyl group, 4-n-butoxyphenoxycarbonyl group, 2,4-dimethoxyphenoxycarbonyl group, 2,3-dimethoxyphenoxycarbonyl group, 2,6-dimethoxyphenoxycarbonyl group, 3,5-dimethoxyphenoxy group Rubonyl group, 2,5-dimethoxyphenoxycarbonyl group, 3,5-ditrifluoromethoxyphenoxycarbonyl group, 3-chloro-4-methoxyphenoxycarbonyl group, 2-chloro-4-trifluoromethoxyphenoxycarbonyl group, 3-methyl -4-fluorophenoxycarbonyl group, 4-bromo-3-trifluoromethylphenoxycarbonyl group, 2-trifluoromethylphenoxycarbonyl group, 3-trifluoromethylphenoxycarbonyl group, 4-trifluoromethylphenoxycarbonyl group, 2- Pentafluoroethylphenoxycarbonyl group, 3-pentafluoroethyl cyphenoxycarbonyl group, 4-pentafluoroethylphenoxycarbonyl group, 2-methoxyphenoxycarbonyl group, 3-methoxyphenoxy group Bonyl group, 4-methoxyphenoxycarbonyl group, 2-ethoxyphenoxycarbonyl group, 3-ethoxyphenoxycarbonyl group, 4-ethoxyphenoxycarbonyl group, 4-n-propoxyphenoxycarbonyl group, 4-tert-butoxyphenoxycarbonyl group, 4 -N-butoxy phenoxycarbonyl group, 2,3- dimethoxy phenoxycarbonyl group, 3, 4, 5- trimethoxy phenoxycarbonyl group, 4- n-pentoxy phenoxycarbonyl group, 4- n-hexyl oxy phenoxycarbonyl group, 2 -Trifluoro methoxy phenoxycarbonyl group, 3- trifluoro methoxy phenoxycarbonyl group, 4- trifluoro methoxy phenoxycarbonyl group, 2- pentafluoro ethoxy phenoxycarbonyl group, 3- penta Phenoxycarbonyl groups such as fluoroethoxyphenoxycarbonyl group, 4-pentafluoroethoxyphenoxycarbonyl group (on the phenyl ring, halogen atoms, halogen-substituted or unsubstituted C1-6 alkyl groups and halogen-substituted or unsubstituted C1-6 1 to 5, preferably 1 to 3 groups selected from the group consisting of alkoxy groups may be mentioned.

  The C1-6 alkoxy substituted C1-6 alkyl group is a group composed of the above C1-6 alkyl group and C1-6 alkoxy group, and examples thereof include a methoxymethyl group, a 2-methoxyethyl group, and a 3-methoxypropyl group. Group, 4-methoxybutyl group, 5-methoxypentyl group, 6-methoxyhexyl group, ethoxymethyl group, 2-ethoxyethyl group, 3-ethoxypropyl group, 2-isopropoxyethyl group, tert-butoxymethyl group, pentyl Oxymethyl group, hexyloxymethyl group, 2- (tert-butoxy) ethyl group, 3- (tert-butoxy) propyl group, 6- (tert-butoxy) hexyl group, 4- (tert-butoxy) butyl group, etc. It can be mentioned.

  As C 2-6 alkenyl group, for example, vinyl group, 2-propenyl group, 3-butenyl group, 2-butenyl group, 4-pentenyl group, 3-pentenyl group, 5-hexenyl group, 4-hexenyl group, 3-Hexenyl group etc. can be mentioned.

  The C1-6 alkoxy substituted C2-6 alkanoyl group is a group composed of the above C1-6 alkyl group and C2-6 alkanoyl group, and is exemplified by, for example, 2-methoxyacetyl group, 2-methoxypropionyl group, 3- Methoxypropionyl group, 4-methoxybutyryl group, 5-methoxypentanoyl group, 6-methoxyhexanoyl group, 2-ethoxyacetyl group, 2-ethoxypropionyl group, 3-ethoxypropionyl group, 2-isopropoxypropionyl group, 2- (tert-butoxy) acetyl group, 2-pentyloxyacetyl group, 2-hexyloxyacetyl group, 2- (tert-butoxy) propionyl group, 3- (tert-butoxy) propionyl group, 6- (tert-butoxy) group ) Hexanoyl group, 4- (tert-butoxy) butyryl group, etc. It can gel.

  The C3-8 cycloalkyl substituted C1-6 alkyl group is a group composed of a cyclic alkyl group having 3 to 8 carbon atoms and an alkyl group having 1 to 6 carbon atoms, and examples thereof include a cyclopropylmethyl group, 2-cyclopropylethyl group, 3-cyclopropylpropyl group, 4-cyclopropylbutyl group, 5-cyclopropylpentyl group, 6-cyclopropylhexyl group, cyclobutylmethyl group, 2-cyclobutylethyl group, 3-cyclo Butylpropyl, 4-cyclobutylbutyl, 5-cyclobutylpentyl, 6-cyclobutylhexyl, cyclopentylmethyl, 2-cyclopentylethyl, 3-cyclopentylpropyl, 4-cyclopentylbutyl, 5-cyclopentyl Pentyl group, 6-cyclopentylhexyl group, cyclohexylmethyl group, -Cyclohexylethyl group, 3-cyclohexylpropyl group, 4-cyclohexylbutyl group, 5-cyclohexylpentyl group, 6-cyclohexylhexyl group, cycloheptylmethyl group, 2-cycloheptylethyl group, 3-cycloheptylpropyl group, 4- Cycloheptylbutyl group, 5-cycloheptylpentyl group, 6-cycloheptylhexyl group, cyclooctylmethyl group, 2-cyclooctylethyl group, 3-cyclooctylpropyl group, 4-cyclooctylbutyl group, 5-cyclooctylpentyl group Group, 6-cyclooctylhexyl group, etc. can be mentioned.

  As the pyridyl C1-6 alkyl group, for example, 2-pyridylmethyl group, 2- (3-pyridyl) ethyl group, 1- (4-pyridyl) ethyl group, 3- (2-pyridyl) propyl group, 4- (4- 3-pyridyl) butyl, 5- (4-pyridyl) pentyl, 6- (2-pyridyl) hexyl, 2-methyl-3- (3-pyridyl) propyl, 1,1-dimethyl-2- ( 2-pyridyl) ethyl etc. can be mentioned.

  The imidazolyl C1-6 alkyl group (a phenyl group may be substituted on the imidazole ring) is, for example, 4-imidazolylmethyl group, 2- (4-imidazolyl) ethyl group, 3- (2-imidazolyl group) ) Propyl group, 4- (1-imidazolyl) butyl group, 5- (5-imidazolyl) pentyl group, 6- (4-imidazolyl) hexyl group, 2,5-diphenyl-1-imidazolylmethyl group, 2-phenyl- 4-imidazolyl methyl group, 2- (2-phenyl-4-imidazolyl) ethyl group, 3- (2-phenyl-4-imidazolyl) propyl group, 4- (2-phenyl-5-imidazolyl) butyl group, 5- Imidazolyl C1-6 alkyl such as (2-phenyl-4-imidazolyl) pentyl, 6- (2-phenyl-4-imidazolyl) hexyl and the like (On the imidazole ring, a phenyl group may be one to two substituents) group and the like.

  1,2,3,4-tetrahydroquinolyl group (on the 1,2,3,4-tetrahydroquinoline ring, at least one of the groups selected from the group consisting of an oxo group and a C.sub.1-6 alkyl group as a substituent) The species may be substituted), for example, 1,2,3,4-tetrahydro-1-quinolyl group, 1,2,3,4-tetrahydro-2-quinolyl group, 1,2,3, 4-tetrahydro-3-quinolyl group, 1,2,3,4-tetrahydro-4-quinolyl group, 1,2,3,4-tetrahydro-5-quinolyl group, 1,2,3,4-tetrahydro-6 -Quinolyl group, 1,2,3,4-tetrahydro-7-quinolyl group, 1,2,3,4-tetrahydro-8-quinolyl group, 2-oxo-1,2,3,4-tetrahydro-1- Quinolyl group, 4-oxo-1,2,3,4-tet Hydro-1-quinolyl group, 2,4-dioxo-1,2,3,4-tetrahydro-1-quinolyl group, 2-oxo-1,2,3,4-tetrahydro-6-quinolyl group, 2-oxo -1,2,3,4-tetrahydro-4-quinolyl group, 2-oxo-1,2,3,4-tetrahydro-7-quinolyl group, 2-oxo-1,2,3,4-tetrahydro-8 group -Quinolyl group, 2-oxo-1,2,3,4-tetrahydro-5-quinolyl group, 2-oxo-1,2,3,4-tetrahydro-3-quinolyl group, 2-methyl-1,2,3 3,4-Tetrahydro-1-quinolyl group, 4-ethyl-1,2,3,4-tetrahydro-1-quinolyl group, 2,4-dimethyl-1,2,3,4-tetrahydro-1-quinolyl group 1,5,6-trimethyl-1,2,3,4-tetraphenyl Ro-1-quinolyl group, 1,4,5,6-tetramethyl-2-oxo-1,2,3,4-tetrahydro-1-quinolyl group, 1-propyl-1,2,3,4-tetrahydro -6-quinolyl group, 5-n-pentyl-1,2,3,4-tetrahydro-4-quinolyl group, 6-n-hexyl-1,2,3,4-tetrahydro-7-quinolyl group, 7- tert-Butyl-1,2,3,4-tetrahydro-8-quinolyl group, 8-n-pentyl-1,2,3,4-tetrahydro-8-quinolyl group, 1-n-hexyl-2-oxo- 1,2,3,4-tetrahydro-8-quinolyl group, 1-methyl-2-oxo-1,2,3,4-tetrahydro-5-quinolyl group, 3-ethyl-2-oxo-1,2,4 1,2,3,4-Teto such as 3,4-tetrahydro-3-quinolyl group Rahydroquinolyl group (1 to 5 groups selected from the group consisting of oxo group and C1-6 alkyl group may be substituted on the 1,2,3,4-tetrahydroquinoline ring) It can be mentioned.

  Examples of the amino group which may have a C1-6 alkyl group as a substituent include, for example, amino group, methylamino group, ethylamino group, n-propylamino group, isopropylamino group, n-butylamino group, tert-butylamino group Group, n-pentylamino group, n-hexylamino group, dimethylamino group, diethylamino group, di-n-propylamino group, di-n-butylamino group, di-n-pentylamino group, di-n-hexyl group Amino group, N-methyl-N-ethylamino group, N-ethyl-N-n-propylamino group, N-methyl-N-n-butylamino group, N-methyl-N-n-hexylamino group, etc. The amino group which may have 1-2 C1-6 alkyl groups as a substituent can be mentioned.

  As a cyano substituted C1-6 alkyl group, for example, cyanomethyl group, 2-cyanoethyl group, 1-cyanoethyl group, 3-cyanopropyl group, 4-cyanobutyl group, 5-cyanopentyl group, 6-cyanohexyl group, 2- Examples thereof include methyl-3-cyanopropyl group and 1,1-dimethyl-2-cyanoethyl group.

  The furyl-substituted C1-6 alkyl group is, for example, 2-furylmethyl group, 3-furylmethyl group, 2- (2-furyl) ethyl group, 1- (3-furyl) ethyl group, 3- (2-furyl) ) Propyl group, 3- (3-furyl) propyl group, 4- (2-furyl) butyl group, 4- (3-furyl) butyl group, 5- (2-furyl) pentyl group, 5- (3-furyl) Pentyl group, 6- (2-furyl) hexyl group, 6- (3-furyl) hexyl group etc. can be mentioned.

  Piperazinyl-substituted C1-6 alkyl group [in the piperazine ring, at least one phenyl group as a substituent (on the phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted group In which at least one group selected from the group consisting of a C.sub.1-6 alkoxy group may be substituted) may be substituted, for example, 1-piperazinylmethyl group, 2- (2-) 2-piperazinyl) ethyl group, 1- (1-piperazinyl) ethyl group, 3- (1-piperazinyl) propyl group, 4- (1-piperazinyl) butyl group, 5- (2-piperazinyl) pentyl group, 6- (6 1-piperazinyl) hexyl group, 2- (4-phenyl-1-piperazinyl) ethyl group, 3- (4-phenyl-1-piperazinyl) propyl group, 4- (4-feline) Nyl-1-piperazinyl) butyl group, 5- (4-phenyl-1-piperazinyl) pentyl group, 6- (4-phenyl-1-piperazinyl) hexyl group, 2- [4- (2-fluorophenyl) -1 -Piperazinyl] ethyl group, 3- [4- (2-fluorophenyl) -1-piperazinyl] propyl group, 4- [4- (2,3-difluorophenyl) -1-piperazinyl] butyl group, 5- [4 -(2-fluorophenyl) -1-piperazinyl] pentyl group, 6- [4- (4-fluorophenyl) -1-piperazinyl] hexyl group, 3- [4- (3-fluorophenyl) -1-piperazinyl] Propyl group, 4- [4- (3-fluorophenyl) -1-piperazinyl] butyl group, 5- [4- (3-fluorophenyl) -1-piperazinyl] pentyl group, 3- 4- (4-fluorophenyl) -1-piperazinyl] propyl group, 4- [4- (4-fluorophenyl) -1-piperazinyl] butyl group, 5- [4- (4-fluorophenyl) -1-piperazinyl] Pentyl group, 6- [4- (4-fluorophenyl) -1-piperazinyl] hexyl group, 2- [4- (2,3-dichlorophenyl) -1-piperazinyl] ethyl group, 3- [4- (2) -Chlorophenyl) -1-piperazinyl] propyl group, 4- [4- (2-chlorophenyl) -1-piperazinyl] butyl group, 5- [4- (2,4,6-trichlorophenyl) -1-piperazinyl] pentyl Group, 6- [4- (2-chlorophenyl) -1-piperazinyl] hexyl group, 2- [4- (3-chlorophenyl) -1-piperazinyl] ethyl group, 3- [4- (4- -Chlorophenyl) -1-piperazinyl] propyl group, 4- [4- (3-chlorophenyl) -1-piperazinyl] butyl group, 5- [4- (2,3,4,5,6-pentafluorophenyl)- 1-piperazinyl! Pentyl group, 6- [4- (3-chloro-4-methylphenyl) -1-piperazinyl] hexyl group, 2- [4- (4-chlorophenyl) -1-piperazinyl] ethyl group, 3- [4- (4-Chlorophenyl) -1-piperazinyl] propyl group, 4- [4- (4-chloro-3-methoxyphenyl) -1-piperazinyl] butyl group, 5- [4- (4-chlorophenyl)- 1-piperazinyl! Pentyl group, 6- [4- (4-chlorophenyl) -1-piperazinyl] hexyl group, 2- [4- (2-methylphenyl) -1-piperazinyl] methyl group , 2- [4- (2,4-dimethylphenyl) -1-piperazinyl] methyl group, 2- [4- (2,4,6-trimethylphenyl) -1-piperazinyl] methyl group, 2- [4- (2-trifluoromethylphenyl) -1-piperazinyl] ethyl group, 3- [4- (3,5-ditrifluoromethylphenyl) -1-piperazinyl] propyl group, 4- [4- (2-trifluoromethyl) Phenyl) -1-piperazinyl] butyl group, 5- [4- (2-trifluoromethylphenyl) -1-piperazinyl] pentyl group, 6- [4- (2-trifluoromethylphenyl) -1-piperazinyl] hexyl Group, 3- [4- (3-trifluoromethylphenyl) -1-piperazinyl] propyl group, 4- [4- (3-trifluoromethylphenyl) -1-piperazinyl] Ethyl, 5- [4- (3-trifluoromethylphenyl) -1-piperazinyl] pentyl, 3- [4- (4-trifluoromethylphenyl) -1-piperazinyl] propyl, 4- [4- (4-Trifluoromethylphenyl) -1-piperazinyl] butyl group, 5- [4- (4-trifluoromethylphenyl) -1-piperazinyl] pentyl group, 6- [4- (4-trifluoromethylphenyl) group -1-piperazinyl! Hexyl group, 2- [4- (3,5-ditrifluoromethoxyphenyl) -1-piperazinyl] ethyl group, 2- [4- (2-methoxyphenyl) -1-piperazinyl] methyl group, 2- [4- (2,4-dimethoxyphenyl) -1-piperazinyl] methyl group, 2- [4- (2,4,6-trimethoxyphenyl) -1-piperazini Methyl group, 3- [4- (2-trifluoromethoxyphenyl) -1-piperazinyl] propyl group, 4- [4- (2-trifluoromethoxyphenyl) -1-piperazinyl] butyl group, 5- [4 -(2-Trifluoromethoxyphenyl) -1-piperazinyl] pentyl, 6- [4- (2-trifluoromethoxyphenyl) -1-piperazinyl] hexyl, 3- [4- (3-trifluoromethoxyphenyl) ) -1-Piperazinyl] propyl group, 4- [4- (3-trifluoromethoxyphenyl) -1-piperazinyl] butyl group, 5- [4- (3-trifluoromethoxyphenyl) -1-piperazinyl] pentyl group , 3- [4- (4-trifluoromethoxyphenyl) -1-piperazinyl] propyl group, 4- [4- (4-trifluoromethoxy) Ciphenyl) -1-piperazinyl] butyl group, 5- [4- (4-trifluoromethoxyphenyl) -1-piperazinyl] pentyl group, 6- [4- (4-trifluoromethoxyphenyl) -1-piperazinyl] hexyl Substituted with a piperazinyl-substituted C.sub.1-6 alkyl group such as a 2,4-diphenyl-1-piperazinylmethyl group, a (2,4,5-triphenyl-1-piperazinyl) methyl group, etc. As a substituent, one to three phenyl groups (on the phenyl ring, selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group 1-5 groups, and preferably 1 to 3 groups may be substituted) may be substituted.

R ^{9 ′} and R ^{10 ′} , R ^{11A ′} and R ^{12A ′} or R ^{11B ′} and R ^{12B ′} , together with adjacent nitrogen atoms, are formed by bonding to each other via or without nitrogen, oxygen or sulfur atoms Examples of the 5- to 7-membered saturated heterocyclic group include pyrrolidinyl group, piperazyl group, piperidyl group, morpholino group, thiomorpholino group, homopiperazinyl group and the like.

1,2,3,4-Tetrahydroisoquinolyl group which R ^{9 ′} and R ^{10 ′} form together with adjacent nitrogen atoms, with or without nitrogen atoms, oxygen atoms or sulfur atoms, or isoindolyl group Group or a 5- to 7-membered saturated heterocyclic ring, a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group, a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group, a phenyl group [on a phenyl ring At least one of a group selected from the group consisting of a phenyl group, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group may be substituted Benzoyl group [in the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group At least one of the groups selected from the group consisting of: pyridyl C.sub.1-6 alkyl group, C.sub.3-8 cycloalkyl group, phenyl C.sub.1-6 alkyl group [on the phenyl ring, C.sub.1-4 At least one group selected from the group consisting of an alkylenedioxy group, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group may be substituted ], Piperidyl C1-6 alkyl group, piperidyl group, phenyl C1-6 alkoxy group [in the phenyl ring, a halogen atom, halogen substituted or unsubstituted C1-6 alkyl group and halogen substituted or unsubstituted C1-6 alkoxy] Group may be substituted by at least one group selected from the group consisting of groups], phenoxy group [on the phenyl ring, a halogen atom, halogen Or at least one of a group selected from the group consisting of an unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted], a phenyl group [phenyl ring as a substituent] At least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group, and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted thereon. , C1-6 alkyl group and phenyl C1-6 alkyl group [in the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group An amino group which may be substituted, at least one of a group selected from the group consisting of at least one of selected groups may be substituted; Group, a group selected from the group consisting of a phenyl C2-6 alkenyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group And at least one group selected from the group consisting of benzimidazolyl groups may be substituted, and as such a substituent, halogen exemplified above and below Atom, halogen-substituted or unsubstituted C1-6 alkyl group and halogen-substituted or unsubstituted C1-6 alkoxy group, phenyl group [in the phenyl ring, a phenyl group, halogen atom, halogen-substituted or unsubstituted C1-6 1 to 5, preferably 1 to 3 groups selected from the group consisting of alkyl groups and halogen-substituted or unsubstituted C1-6 alkoxy groups are substituted Benzoyl group [in the phenyl ring, a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group, a halogen substituted or unsubstituted C1-6 alkoxy group, -5, preferably 1 to 3 substituents, pyridyl C1-6 alkyl group, C3-8 cycloalkyl group, phenyl C1-6 alkyl group [on phenyl ring, C1 to 4 alkylene group 1 to 5, preferably 1 to 3 groups selected from the group consisting of an oxy group, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group It may be done. When the substituent is a C1 to 4 alkylenedioxy group, one to two substituents should be substituted], piperidyl C1 to C6 alkyl group, piperidyl group, phenyl C1 to C6 alkoxy group [a halogen atom on a phenyl ring And 1 to 5, preferably 1 to 3 groups selected from the group consisting of halogen-substituted or unsubstituted C1-6 alkyl groups and halogen-substituted or unsubstituted C1-6 alkoxy groups may be substituted Phenoxy group [1 to 5 groups selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group on the phenyl ring And preferably 1 to 3 substituents], a phenyl group as a substituent [on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted 1 to 5, preferably 1 to 3 groups selected from the group consisting of unsubstituted C1-6 alkoxy groups may be substituted], C1-6 alkyl groups and phenyl C1-6 alkyl groups [phenyl There are 1 to 5 groups, preferably 1 to 3 groups selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group on the ring. Amino group which may be substituted one to two groups selected from the group consisting of [optionally substituted], benzoxazolyl group, phenyl C.sub.2-6 alkenyl group (on the phenyl ring, halogen A group consisting of an atom, a halogen-substituted or unsubstituted linear or branched alkyl group having 1 to 6 carbon atoms, and a halogen-substituted or unsubstituted linear or branched alkoxy group having 1 to 6 carbon atoms 1 to 5 groups selected from Preferably 1 to 3 substituents and may be) and a group selected from the group consisting of benzimidazolyl group may be one to three substituents.

On the 5- to 7-membered saturated heterocycle formed by R ^{11B ′} and R ^{12B ′} , together with the adjacent nitrogen atom, being bonded to each other without or through the nitrogen atom, oxygen atom or sulfur atom, C 1 To 6 alkoxycarbonyl group and amino group [amino group [phenyl group (on the phenyl group, halogen atom, halogen substituted or unsubstituted C1-6 alkyl group and halogen substituted or unsubstituted C1-6 alkoxy group And at least one group selected from the group consisting of C 1 to 6 alkyl groups may be substituted) At least one of the selected groups may be substituted, and as such a substituent, a C1-6 alkoxycarbonyl group and an amino group [an amino group represented by (1 to 5 groups selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group on a phenyl ring, preferably Is a group selected from the group consisting of 1 to 3) and a group selected from the group consisting of a C1 to 6 alkyl group]; and groups selected from the group consisting of These substituents may be substituted by 1 to 3 on the heterocyclic ring.

  Phenyl group [in which at least one group selected from the group consisting of a phenyl group, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group on a phenyl ring Is optionally substituted] means an unsubstituted phenyl group, a phenyl group as defined above, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy. A phenyl group having 1 to 5, preferably 1 to 3 substituents selected from the group consisting of: phenyl group, 2-phenylphenyl group, 3-phenylphenyl group, 4-phenylphenyl group, 2,3-Diphenylphenyl, 2,4,6-triphenylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group Group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 2-bromophenyl group, 3-bromophenyl group, 4-bromophenyl group, 2-iodophenyl group, 3-iodo Phenyl group, 4-iodophenyl group, 2,3-difluorophenyl group, 3,4-difluorophenyl group, 3,5-difluorophenyl group, 2,4-difluorophenyl group, 2,6-difluorophenyl group, 2 , 3-dichlorophenyl group, 3,4-dichlorophenyl group, 3,5-dichlorophenyl group, 2,4-dichlorophenyl group, 2,6-dichlorophenyl group, 3,4,5-trifluorophenyl group, 3,4,5 -Trichlorophenyl group, 2,4,6-trifluorophenyl group, 2,4,6-trichlorophenyl group, 2-full Ro-4-bromophenyl, 4-chloro-3-fluorophenyl, 2,3,4-trichlorophenyl, 3,4,5-trifluorophenyl, 2,3,4,5,6-penta Fluorophenyl group, 2,4,6-trimethylphenyl group, 4-n-butylphenyl group, 2,4-dimethylphenyl group, 2,3-dimethylphenyl group, 2,6-dimethylphenyl group, 3,5- Dimethylphenyl group, 2,5-dimethylphenyl group, 3,5-ditrifluoromethylphenyl group, 4-n-butoxyphenyl group, 2,4-dimethoxyphenyl group, 2,3-dimethoxyphenyl group, 2,6- Dimethoxyphenyl group, 3,5-dimethoxyphenyl group, 2,5-dimethoxyphenyl group, 2,4,6-trimethoxyphenyl group, 3,5-ditrifluoromethoxyphene Group, 3-chloro-4-methoxyphenyl group, 2-chloro-4-trifluoromethoxyphenyl group, 3-methyl-4-fluorophenyl group, 4-bromo-3-trifluoromethylphenyl group, 2-methyl group Phenyl group, 3-methylphenyl group, 4-methylphenyl group, 2-methyl-3-chlorophenyl group, 3-methyl-4-chlorophenyl group, 2-chloro-4-methylphenyl group, 2-methyl-3-fluoro Phenyl group, 2-trifluoromethylphenyl group, 3-trifluoromethylphenyl group, 4-trifluoromethylphenyl group, 2-pentafluoroethylphenyl group, 3-pentafluoroethylphenyl group, 4-pentafluoroethylphenyl group , 2-isopropylphenyl group, 3-isopropylphenyl group, 4-isopropylpheny Group, 2-tert-butylphenyl group, 3-tert-butylphenyl group, 4-tert-butylphenyl group, 2-sec-butylphenyl group, 3-sec-butylphenyl group, 4-sec-butylphenyl group, 2-n-heptafluoropropylphenyl group, 3-n-heptafluoropropylphenyl group, 4-n-heptafluoropropylphenyl group, 4-n-pentylphenyl group, 4-n-hexylphenyl group, 2-methoxyphenyl group Group, 3-methoxyphenyl group, 4-methoxyphenyl group, 3-chloro-2-methoxyphenyl group, 2-fluoro-3-methoxyphenyl group, 2-fluoro-4-methoxyphenyl group, 2,6-dimethoxyphenyl group Group, 2,3,4-trifluorophenyl group, 2,4,6-trifluorophenyl group, 2-to Fluoromethoxyphenyl group, 3-trifluoromethoxyphenyl group, 4-trifluoromethoxyphenyl group, 3-fluoro-2-trifluoromethoxyphenyl group, 2-fluoro-3-trifluoromethoxyphenyl group, 3-fluoro-4 -Trifluoromethoxyphenyl group, 3-chloro-2-trifluoromethoxyphenyl group, 2-chloro-3-trifluoromethoxyphenyl group, 3-chloro-4-trifluoromethoxyphenyl group, 2-pentafluoroethoxyphenyl group , 3-pentafluoroethoxyphenyl group, 4-pentafluoroethoxyphenyl group, 3-chloro-2-pentafluoroethoxyphenyl group, 2-chloro-3-pentafluoroethoxyphenyl group, 3-chloro-4-pentafluoroethoxy Phenyl group, 2-iso Propoxyphenyl group, 3-isopropoxyphenyl group, 4-isopropoxyphenyl group, 2-tert-butoxyphenyl group, 3-tert-butoxyphenyl group, 4-tert-butoxyphenyl group, 2-sec-butoxyphenyl group, 3-sec-butoxyphenyl group, 4-sec-butoxyphenyl group, 2-n-heptafluoropropoxyphenyl group, 3-n-heptafluoropropoxyphenyl group, 4-n-heptafluoropropoxyphenyl group, 4-n- A pentoxyphenyl group, 4-n-hexyl oxyphenyl group etc. can be mentioned.

  Phenyl C1-6 alkoxy group [in which at least one of the groups selected from the group consisting of halogen atoms, halogen substituted or unsubstituted C1-6 alkyl groups and halogen substituted or unsubstituted C1-6 alkoxy groups on the phenyl ring The species may be substituted] is a group selected from the group consisting of a halogen atom as defined above, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group Is a phenyl C1-6 alkoxy group which may be substituted by 1 to 5, preferably 1 to 3 groups, and examples thereof include a benzyloxy group, a 2-phenylethoxy group, a 3-phenylpropoxy group and a 2-phenylpropoxy group. Group, 4-phenylbutoxy group, 5-phenylpentoxy group, 4-phenylpentoxy group, 6-phenylhexyloxy , 2-fluorobenzyloxy group, 3-fluorobenzyloxy group, 4-fluorobenzyloxy group, 2- (2-fluorophenyl) ethoxy group, 2- (3-fluorophenyl) ethoxy group, 2- (4-fluoro) Phenyl) ethoxy group, 2-chlorobenzyloxy group, 3-chlorobenzyloxy group, 4-chlorobenzyloxy group, 2-fluoro-4-bromobenzyloxy group, 4-chloro-3-fluorobenzyloxy group, 2- Chloro-4-fluorobenzyloxy group, 3,4-dichlorobenzyloxy group, 3,5-dichlorobenzyloxy group, 2,3-dichlorobenzyloxy group, 2,5-dichlorobenzyloxy group, 2, 3, 4 -Trichlorobenzyloxy group, 3,4,5-trifluorobenzyloxy group, 2,3,4,5,6-pen Fluorobenzyloxy group, 2,4,6-trichlorobenzyloxy group, 4-isopropylbenzyloxy group, 4-n-butylbenzyloxy group, 4-methylbenzyloxy group, 2-methylbenzyloxy group, 3-methylbenzyl Oxy group, 2,4-dimethylbenzyloxy group, 2,3-dimethylbenzyloxy group, 2,6-dimethylbenzyloxy group, 3,5-dimethylbenzyloxy group, 2,5-dimethylbenzyloxy group, 2, 4,6-trimethylbenzyloxy group, 4-ethylbenzyloxy group, 4-isopropylbenzyloxy group, 3,5-ditrifluoromethylbenzyloxy group, 4-isopropoxybenzyloxy group, 4-n-butoxybenzyloxy group , 4-methoxybenzyloxy group, 2-methoxybenzyloxy group, 3 -Methoxybenzyloxy group, 2,4-dimethoxybenzyloxy group, 2,3-dimethoxybenzyloxy group, 2,6-dimethoxybenzyloxy group, 3,5-dimethoxybenzyloxy group, 2,5-dimethoxybenzyloxy group 2,4,6-trimethoxybenzyloxy group, 3,5-ditrifluoromethoxybenzyloxy group, 2-isopropoxybenzyloxy group, 3-chloro-4-methoxybenzyloxy group, 2-chloro-4-trihydroxy group Fluoromethoxybenzyloxy group, 3-methyl-4-fluorobenzyloxy group, 4-bromo-3-trifluoromethylbenzyloxy group, 2- (2-chlorophenyl) ethoxy group, 2- (3-chlorophenyl) ethoxy group, 2- (4-chlorophenyl) ethoxy group, 2-trifluoromethylbenzyl Oxy group, 3-trifluoromethylbenzyloxy group, 4-trifluoromethylbenzyloxy group, 2-trifluoromethoxybenzyloxy group, 3-trifluoromethoxybenzyloxy group, 4-trifluoromethoxybenzyloxy group, 2- (2-trifluoromethylphenyl) ethoxy group, 2- (3-trifluoromethylphenyl) ethoxy group, 2- (4-trifluoromethylphenyl) ethoxy group, 2- (2-trifluoromethoxyphenyl) ethoxy group, 2- (3-trifluoromethoxyphenyl) ethoxy group, 2- (4-trifluoromethoxyphenyl) ethoxy group, 3- (2-trifluoromethylphenyl) propoxy group, 3- (3-trifluoromethylphenyl) propoxy Group, 3- (4-trifluoromethylphenyl) Lopoxy group, 3- (2-trifluoromethylphenyl) propoxy group, 3- (3-trifluoromethoxyphenyl) propoxy group, 3- (4-trifluoromethoxyphenyl) propoxy group, 4- (3-trifluoromethyl) Phenyl) butoxy group, 5- (4-trifluoromethylphenyl) pentoxy group, 4- (4- trifluoromethylphenyl) pentoxy group, 4- (4- trifluoromethoxyphenyl) pentoxy group, 6- (3- tritoxy group Examples include fluoromethylphenyl) hexyloxy group, 6- (4-trifluoromethylphenyl) hexyloxy group, 6- (4-trifluoromethoxyphenyl) hexyloxy group and the like.

  At least one member selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group is substituted on the phenoxy group [phenyl ring; And the like] is selected from the group consisting of an unsubstituted phenoxy group and a halogen atom as defined above, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group Phenoxy group having 1 to 5 and preferably 1 to 3 substituents, such as phenoxy group, 2-fluorophenoxy group, 3-fluorophenoxy group, 4-fluorophenoxy group, 2-chlorophenoxy group , 3-chlorophenoxy group, 4-chlorophenoxy group, 2-bromophenoxy group, 3-bromophenoxy Group, 4-bromophenoxy group, 2-iodophenoxy group, 3-iodophenoxy group, 4-iodophenoxy group, 2,3-difluorophenoxy group, 3,4-difluorophenoxy group, 3,5-difluorophenoxy group, 2,4-difluorophenoxy group, 2,6-difluorophenoxy group, 2,3-dichlorophenoxy group, 3,4-dichlorophenoxy group, 3,5-dichlorophenoxy group, 2,4-dichlorophenoxy group, 2, 6-dichlorophenoxy group, 3,4,5-trifluorophenoxy group, 3,4,5-trichlorophenoxy group, 2,4,6-trifluorophenoxy group, 2,4,6-trichlorophenoxy group, 2- Fluoro-4-bromophenoxy group, 4-chloro-3-fluorophenoxy group, 2,3,4-trichlorophenol Group, 3,4,5-trifluorophenoxy group, 2,3,4,5,6-pentafluorophenoxy group, 2,4,6-trimethylphenoxy group, 4-n-butylphenoxy group, 2,4- Dimethylphenoxy group, 2,3-dimethylphenoxy group, 2,6-dimethylphenoxy group, 3,5-dimethylphenoxy group, 2,5-dimethylphenoxy group, 3,5-ditrifluoromethylphenoxy group, 4-n- Butoxyphenoxy group, 2,4-dimethoxyphenoxy group, 2,3-dimethoxyphenoxy group, 2,6-dimethoxyphenoxy group, 3,5-dimethoxyphenoxy group, 2,5-dimethoxyphenoxy group, 2,4,6- Trimethoxyphenoxy group, 3,5-ditrifluoromethoxyphenoxy group, 3-chloro-4-methoxyphenoxy group, 2-chloro -4-trifluoromethoxyphenoxy group, 3-methyl-4-fluorophenoxy group, 4-bromo-3-trifluoromethylphenoxy group, 2-methylphenoxy group, 3-methylphenoxy group, 4-methylphenoxy group, 2 -Methyl-3-chlorophenoxy group, 3-methyl-4-chlorophenoxy group, 2-chloro-4-methylphenoxy group, 2-methyl-3-fluorophenoxy group, 2-trifluoromethylphenoxy group, 3-trile Fluoromethyl phenoxy group, 4-trifluoromethyl phenoxy group, 2-pentafluoroethyl phenoxy group, 3-pentafluoroethyl phenoxy group, 4-pentafluoroethyl phenoxy group, 2-isopropyl phenoxy group, 3-isopropyl phenoxy group, 4 -Isopropylphenoxy group, 2-ter -Butylphenoxy group, 3-tert-butylphenoxy group, 4-tert-butylphenoxy group, 2-sec-butylphenoxy group, 3-sec-butylphenoxy group, 4-sec-butylphenoxy group, 2-n-hepta Fluoropropylphenoxy group, 3-n-heptafluoropropylphenoxy group, 4-n-heptafluoropropylphenoxy group, 4-n-pentylphenoxy group, 4-n-hexylphenoxy group, 2-methoxyphenoxy group, 3-methoxy Phenoxy group, 4-methoxyphenoxy group, 3-chloro-2-methoxyphenoxy group, 2-fluoro-3-methoxyphenoxy group, 2-fluoro-4-methoxyphenoxy group, 2,6-dimethoxyphenoxy group, 2, 3 , 4-Trifluorophenoxy group, 2,4,6-triful Rophenoxy group, 2-trifluoromethoxyphenoxy group, 3-trifluoromethoxyphenoxy group, 4-trifluoromethoxyphenoxy group, 3-fluoro-2-trifluoromethoxyphenoxy group, 2-fluoro-3-trifluoromethoxyphenoxy Group, 3-fluoro-4-trifluoromethoxyphenoxy group, 3-chloro-2-trifluoromethoxyphenoxy group, 2-chloro-3-trifluoromethoxyphenoxy group, 3-chloro-4-trifluoromethoxyphenoxy group, 2-pentafluoroethoxyphenoxy group, 3-pentafluoroethoxyphenoxy group, 4-pentafluoroethoxyphenoxy group, 3-chloro-2-pentafluoroethoxyphenoxy group, 2-chloro-3-pentafluoroethoxyphenoxy group, 3- The Rolo-4-pentafluoroethoxyphenoxy group, 2-isopropoxyphenoxy group, 3-isopropoxyphenoxy group, 4-isopropoxyphenoxy group, 2-tert-butoxyphenoxy group, 3-tert-butoxyphenoxy group, 4-tert 4-butoxyphenoxy group, 2-sec-butoxyphenoxy group, 3-sec-butoxyphenoxy group, 4-sec-butoxyphenoxy group, 2-n-heptafluoropropoxyphenoxy group, 3-n-heptafluoropropoxyphenoxy group, 4 And -n-heptafluoropropoxyphenoxy group, 4-n-pentoxyphenoxy group, 4-n-hexyloxyphenoxy group and the like can be mentioned.

  Phenyl C1-6 alkyl group [wherein on the phenyl ring, a C1-4 alkylenedioxy group, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group At least one of the selected groups may be substituted] means an unsubstituted phenyl C.sub.1-6 alkyl group and a C.sub.1-4 alkylenedioxy group on the phenyl ring constituting those groups, a halogen atom A group in which 1 to 5, preferably 1 to 3 groups selected from the group consisting of a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group are substituted ((1) When the substituent is a C1-4 alkylenedioxy group, one to two substituents may be substituted), and examples thereof include a benzyl group, a 1-phenethyl group and a 2-phenyl group. Netyl group, 3-phenylpropyl group, 2-phenylpropyl group, 4-phenylbutyl group, 5-phenylpentyl group, 4-phenylpentyl group, 6-phenylhexyl group, 2,3-methylenedioxybenzyl group, 3 , 4-Methylenedioxybenzyl group, 2-fluorobenzyl group, 3-fluorobenzyl group, 4-fluorobenzyl group, 2-chlorobenzyl group, 3-chlorobenzyl group, 4-chlorobenzyl group, 2-bromobenzyl group , 3-bromobenzyl group, 4-bromobenzyl group, 2-iodobenzyl group, 3-iodobenzyl group, 4-iodobenzyl group, 2,3-difluorobenzyl group, 3,4-difluorobenzyl group, 3,5 -Difluorobenzyl group, 2,4-difluorobenzyl group, 2,6-difluorobenzyl group, 2,3-dichloroben Group, 3,4-dichlorobenzyl group, 3,5-dichlorobenzyl group, 2,4-dichlorobenzyl group, 2,6-dichlorobenzyl group, 2-fluoro-4-bromobenzyl group, 4-chloro-3 -Fluorobenzyl group, 2,3,4-trichlorobenzyl group, 3,4,5-trifluorobenzyl group, 2,4,6-trichlorobenzyl group, 4-isopropylbenzyl group, 4-n-butylbenzyl group, 4-methylbenzyl group, 2-methylbenzyl group, 3-methylbenzyl group, 2,4-dimethylbenzyl group, 2,3-dimethylbenzyl group, 2,6-dimethylbenzyl group, 3,5-dimethylbenzyl group, 2,5-dimethylbenzyl, 2,4,6-trimethylbenzyl, 3,5-ditrifluoromethylbenzyl, 2,3,4,5,6-pentafluoroben Dyl, 4-isopropoxybenzyl, 4-n-butoxybenzyl, 4-methoxybenzyl, 2-methoxybenzyl, 3-methoxybenzyl, 2,4-dimethoxybenzyl, 2,3-dimethoxybenzyl Group, 2,6-dimethoxybenzyl group, 3,5-dimethoxybenzyl group, 2,5-dimethoxybenzyl group, 2,4,6-trimethoxybenzyl group, 3,5-ditrifluoromethoxybenzyl group, 2-iso Propoxybenzyl group, 3-chloro-4-methoxybenzyl group, 2-chloro-4-trifluoromethoxybenzyl group, 3-methyl-4-fluorobenzyl group, 4-bromo-3-trifluoromethylbenzyl group, 2- Trifluoromethylbenzyl group, 3-trifluoromethylbenzyl group, 4-trifluoromethylbenzyl group, 2 Pentafluoroethyl benzyl group, 3-pentafluoroethyl benzyl group, 4-pentafluoroethyl benzyl group, 2-trifluoromethoxybenzyl group, 3-trifluoromethoxybenzyl group, 4-trifluoromethoxybenzyl group, 2-pentafluoro Ethoxybenzyl group, 3-pentafluoroethoxybenzyl group, 4-pentafluoroethoxybenzyl group, 2- (2-trifluoromethylphenyl) ethyl group, 2- (3-trifluoromethylphenyl) ethyl group, 2- (4 -Trifluoromethylphenyl) ethyl group, 2- (2-trifluoromethoxyphenyl) ethyl group, 3-trifluoromethoxyphenyl) ethyl group, 2- (4-trifluoromethoxyphenyl) ethyl group, 2- (2- Pentafluoroethoxyphenyl) ethyl group 2- (3-Pentafluoroethoxyphenyl) ethyl group, 2- (4-pentafluoroethoxyphenyl) ethyl group, 3- (2-trifluoromethylphenyl) propyl group, 3- (3-trifluoromethylphenyl) propyl Group, 3- (4-trifluoromethylphenyl) propyl group, 3- (2-trifluoromethoxyphenyl) propyl group, 3- (3-trifluoromethoxyphenyl) propyl group, 3- (4-trifluoromethoxyphenyl) group ) Propyl group, 3- (3-pentafluoroethoxyphenyl) propyl group, 3- (4-pentafluoroethoxyphenyl) propyl group, 4- (3-pentafluoroethoxyphenyl) butyl group, 5- (4-trifluoro) Methylphenyl) pentyl group, 4- (4-trifluoromethylphenyl) pentyl Group, 4- (4-trifluoromethoxyphenyl) pentyl group, 6- (3-trifluoromethylphenyl) hexyl group, 6- (4-trifluoromethylphenyl) hexyl group, 6- (4-trifluoromethoxyphenyl) Hexyl group etc. can be mentioned.

  As a piperidyl C1-6 alkyl group, for example, piperidin-1-ylmethyl group, piperidin-2-ylethyl group, piperidin-3-ylpropyl group, piperidin-4-ylbutyl group, piperidin-1-ylpentyl group, piperidine-2 -Hexyl group etc. can be mentioned.

  As a substituent, a phenyl group [in the phenyl ring, at least one group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group] C1-6 alkyl group and phenyl C1-6 alkyl group [in the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1 Examples of the amino group which may be substituted by at least one group selected from the group consisting of -6 alkoxy group may be substituted by at least one group selected from the group consisting of Amino group, methylamino group, dimethylamino group, ethylamino group, diethylamino group, n-propylamino group, n-butylamino group, n-pentylamine Group, n-hexylamino group, phenylamino group, (4-chlorophenyl) amino group, (4-bromophenyl) amino group, (2,4-dichlorophenyl) amino group, (2,4,6-trichlorophenyl) amino Group, (2,3,4,5,6-pentafluorophenyl) amino group, (4-fluorophenyl) amino group, (4-iodophenyl) amino group, (4-chlorophenyl) amino group, (3-methyl) (Phenyl) amino group, (2-trifluoromethylphenyl) amino group, (3-trifluoromethylphenyl) amino group, (4-trifluoromethylphenyl) amino group, (3,4-dimethylphenyl) amino group, 3,4,5-trimethylphenyl) amino group, (2-methoxyphenyl) amino group, (4-trifluoromethoxyphenyl) amide Group, (3-trifluoromethoxyphenyl) amino group, (3,5-dimethoxyphenyl) amino group, (2,5-dimethoxyphenyl) amino group, (2,4,6-trimethoxyphenyl) amino group, N -Methyl-N- (4-trifluoromethylphenyl) amino group, N-ethyl-N- (4-trifluoromethoxyphenyl) amino group, 1-phenethylamino group, 2-phenethylamino group, 3-phenylpropylamino Group, 2-phenylpropylamino group, 4-phenylbutylamino group, 5-phenylpentylamino group, 4-phenylpentylamino group, 6-phenylhexylamino group, 2-fluorobenzylamino group, 3-fluorobenzylamino group , N-phenyl-N- (4-fluorobenzyl) amino group, 2-chlorobenzylamino group, 3 -Chlorobenzylamino group, 4-chlorobenzylamino group, 2-bromobenzylamino group, N-methyl-N- (3-bromobenzyl) amino group, 4-bromobenzylamino group, 2-iodobenzylamino group, 3 -Iodobenzylamino group, 4-iodobenzylamino group, 2,3-difluorobenzylamino group, 3,4-difluorobenzylamino group, 3,5-difluorobenzylamino group, 2,4-difluorobenzylamino group, 2 , 6-Difluorobenzylamino group, 2,3-dichlorobenzylamino group, 3,4-dichlorobenzylamino group, 3,5-dichlorobenzylamino group, 2,4-dichlorobenzylamino group, 2,6-dichlorobenzyl Amino group, 2-fluoro-4-bromobenzylamino group, 4-chloro-3-fluorobenzyl Mino group, 2,3,4-trichlorobenzylamino group, 3,4,5-trifluorobenzylamino group, 2,4,6-trichlorobenzylamino group, 4-isopropylbenzylamino group, 4-n-butylbenzyl Amino group, 4-methylbenzylamino group, 2-methylbenzylamino group, 3-methylbenzylamino group, 2,4-dimethylbenzylamino group, 2,3-dimethylbenzylamino group, 2,6-dimethylbenzylamino group , 3,5-dimethylbenzylamino, 2,5-dimethylbenzylamino, 2,4,6-trimethylbenzylamino, 3,5-ditrifluoromethylbenzylamino, 2,3,4,5,6 -Pentafluorobenzylamino group, 4-isopropoxybenzylamino group, 4-n-butoxybenzylamino group, 4-methane Xybenzylamino, 2-methoxybenzylamino, 3-methoxybenzylamino, 2,4-dimethoxybenzylamino, 2,3-dimethoxybenzyl, 2,6-dimethoxybenzylamino, 3,5-dimethoxy Benzylamino, 2,5-dimethoxybenzylamino, 2,4,6-trimethoxybenzylamino, 3,5-ditrifluoromethoxybenzylamino, 2-isopropoxybenzylamino, 3-chloro-4- Methoxybenzylamino group, 2-chloro-4-trifluoromethoxybenzylamino group, 3-methyl-4-fluorobenzylamino group, 4-bromo-3-trifluoromethylbenzylamino group, 2-trifluoromethylbenzylamino group , 3-trifluoromethylbenzylamino group, 4-trifluoro Methyl benzylamino group, 2-pentafluoroethyl benzylamino group, 3-pentafluoroethyl benzylamino group, 4-pentafluoroethyl benzylamino group, 2-trifluoromethoxybenzylamino group, 3-trifluoromethoxybenzylamino group , 4-Trifluoromethoxybenzylamino group, 2-pentafluoroethoxybenzylamino group, 3-pentafluoroethoxybenzylamino group, 4-pentafluoroethoxybenzylamino group, 2- (2-trifluoromethylphenyl) ethylamino group , 2- (3-trifluoromethylphenyl) ethylamino group, 2- (4-trifluoromethylphenyl) ethylamino group, 2- (2-trifluoromethoxyphenyl) ethylamino group, 2- (3-trifluoro) Methoxyphenyl Ethylamino group, 2- (4-trifluoromethoxyphenyl) ethylamino group, 2- (2-pentafluoroethoxyphenyl) ethylamino group, 2- (3-pentafluoroethoxyphenyl) ethylamino group, 2- (4 -Pentafluoroethoxyphenyl) ethylamino group, 3- (2-trifluoromethylphenyl) propylamino group, 3- (3-trifluoromethylphenyl) propylamino group, 3- (4-trifluoromethylphenyl) propylamino Group, 3- (2-trifluoromethoxyphenyl) propylamino group, 3- (3-trifluoromethoxyphenyl) propylamino group, 3- (4-trifluoromethoxyphenyl) propylamino group, 3- (3-penta) Fluoroethoxyphenyl) propylamino group, 3- (4-penta) Fluoroethoxyphenyl) propylamino group, 4- (3-pentafluoroethoxyphenyl) butylamino group, 5- (4-trifluoromethylphenyl) pentylamino group, 4- (4-trifluoromethylphenyl) pentylamino group , 4- (4-trifluoromethoxyphenyl) pentylamino group, 6- (3-trifluoromethylphenyl) hexylamino group, 6- (4-trifluoromethylphenyl) hexylamino group, 6- (4-trifluoro) As a substituent group such as methoxyphenyl) hexylamino group, N-methyl-N-phenylamino group, N-methyl-N-benzylamino group, N-phenyl-N-benzylamino group, etc. A halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted 1 to 5, preferably 1 to 3, groups selected from the group consisting of substituted C1-6 alkoxy groups may be substituted], C1-6 alkyl groups and phenyl C1-6 alkyl groups [phenyl ring Above, 1-5 groups, preferably 1-3 groups selected from the group consisting of halogen atoms, halogen-substituted or unsubstituted C1-6 alkyl groups and halogen-substituted or unsubstituted C1-6 alkoxy groups The amino group which may be substituted may be one to two groups selected from the group consisting of [optionally substituted].

  A phenyl C1-6 alkyl group (on the phenyl ring, a halogen atom, a phenyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group, and a halogen substituted or unsubstituted C1-6 alkoxy At least one group selected from the group consisting of groups may be substituted), selected from the group consisting of halogen-substituted or unsubstituted C1-6 alkyl groups and halogen-substituted or unsubstituted C1-6 alkoxy groups Examples of the phenyl C 1-6 alkyl group (on the phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C 1-6 alkyl group and a halogen) include 4- (4-T) in addition to at least one of a group selected from the group consisting of a substituted or unsubstituted C1-6 alkoxy group may be substituted) Fluoromethylphenyl) benzyl group, 4- (4-trifluoromethoxyphenyl) benzyl group, 4- (4-chlorophenyl) benzyl group, 4- (4-trifluoromethylphenyl) benzyl group, 4-phenylbenzyl group, 3 -Alkyl such as phenylbenzyl group, 3,4-diphenylbenzyl group, 3,4,5-triphenylbenzyl group, 4-nitro-3-trifluoromethylbenzyl group, 4-trifluoromethoxy-3-phenylbenzyl group A phenylalkyl group in which the moiety is a linear or branched alkyl group having 1 to 6 carbon atoms (a halogen atom on the phenyl ring, a halogen group on the phenyl ring (a halogen atom on the phenyl ring, or a halogen atom substituted or unsubstituted 1 to 5 groups selected from the group consisting of a C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group A group selected from the group consisting of a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group, which may be substituted preferably 1 to 3) is preferably 1 to 5 And preferably 1 to 3 substituents may be mentioned.

  A carbamoyloxy group (on the amino group, a C1-6 alkyl group and a phenyl group [a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy on the phenyl ring At least one group selected from the group consisting of groups may be substituted], and at least one group selected from the group consisting of groups may be substituted), for example, a carbamoyloxy group, Phenylcarbamoyloxy group, 2-fluorophenylcarbamoyloxy group, 3-fluorophenylcarbamoyloxy group, 4-fluorophenylcarbamoyloxy group, 2-chlorophenylcarbamoyloxy group, 3-chlorophenylcarbamoyloxy group, 4-chlorophenylcarbamoyloxy group, 2-bromophenylcarbamoylo , 3-bromophenylcarbamoyloxy group, 4-bromophenylcarbamoyloxy group, 2-iodophenylcarbamoyloxy group, 3-iodophenylcarbamoyloxy group, 4-iodophenylcarbamoyloxy group, 2,3-difluorophenylcarbamoyl group Oxy group, 3,4-difluorophenylcarbamoyloxy group, 3,5-difluorophenylcarbamoyloxy group, 2,4-difluorophenylcarbamoyloxy group, 2,6-difluorophenylcarbamoyloxy group, 2,3-dichlorophenylcarbamoyloxy group Group, 3,4-dichlorophenylcarbamoyloxy group, 3,5-dichlorophenylcarbamoyloxy group, 2,4-dichlorophenylcarbamoyloxy group, 2,6-dichlorophenylcarbamoyl group Oxy group, 3,4,5-trifluorophenylcarbamoyloxy group, 2,3,4,5,6-pentafluorophenylcarbamoyloxy group, 3,4,5-trichlorophenylcarbamoyloxy group, 2,4,6 -Trifluorophenylcarbamoyloxy group, 2,4,6-trichlorophenylcarbamoyloxy group, 2-methylphenylcarbamoyloxy group, 3-methylphenylcarbamoyloxy group, 4-methylphenylcarbamoyloxy group, 2-methyl-3- Chlorophenylcarbamoyloxy group, 3-methyl-4-chlorophenylcarbamoyloxy group, 2-chloro-4-methylphenylcarbamoyloxy group, 2-methyl-3-fluorophenylcarbamoyloxy group, 2-trifluoromethylphenylcarbamoyloxy group , 3-trifluoromethylphenylcarbamoyloxy group, methylcarbamoyloxy group, ethylcarbamoyloxy group, n-propylcarbamoyloxy group, n-butylcarbamoyloxy group, n-hexylcarbamoyloxy group, n-pentylcarbamoyloxy group, N -Methyl-N-phenylcarbamoyloxy group, N, N-dimethylcarbamoyloxy group, N-methyl-N-ethylcarbamoyloxy group, N- (2-fluorophenyl) -N-methylcarbamoyloxy group, N- (3 -Fluorophenyl) -N-methylcarbamoyloxy group, N- (4-fluorophenyl) -N-methylcarbamoyloxy group, N- (2-chlorophenyl) -N-methylcarbamoyloxy group, N- (3-chlorophenyl) group -N-methylcarbamoyl Oxy group, N- (4-chlorophenyl) -N-methylcarbamoyloxy group, N- (4-bromophenyl) -N-methylcarbamoyloxy group, N- (2-iodophenyl) -N-methylcarbamoyloxy group, N- (3-iodophenyl) -N-methylcarbamoyloxy group, N- (4-iodophenyl) -N-methylcarbamoyloxy group, N- (2,3-difluorophenyl) -N-methylcarbamoyloxy group, N- (3,4-difluorophenyl) -N-methylcarbamoyloxy group, N- (3,5-difluorophenyl) -N-methylcarbamoyloxy group, N- (2,4-difluorophenyl) -N-methyl A carbamoyloxy group, N- (2,6-difluorophenyl) -N-methylcarbamoyloxy group, N- (2,3-) Chlorophenyl) -N-methylcarbamoyloxy group, N- (3,4-dichlorophenyl) -N-methylcarbamoyloxy group, N- (3,5-dichlorophenyl) -N-methylcarbamoyloxy group, N- (2,4 (2,4) -Dichlorophenyl) -N-methylcarbamoyloxy group, N- (2,6-dichlorophenyl) -N-methylcarbamoyloxy group, N- (3,4,5-trifluorophenyl) -N-methylcarbamoyloxy group, N -(3,4,5-trichlorophenyl) -N-methylcarbamoyloxy group, N- (2,4,6-trifluorophenyl) -N-methylcarbamoyloxy group, N- (2,4,6-triyl group Chlorophenyl) -N-methylcarbamoyloxy group, N- (2-methylphenyl) -N-methylcarbamoyloxy group, N- (3-methylphenyl) -N-methylcarbamoyloxy group, N- (4-methylphenyl) -N-methylcarbamoyloxy group, N- (2-methyl-3-chlorophenyl) -N-methylcarbamoyloxy group N- (3-methyl-4-chlorophenyl) -N-methylcarbamoyloxy group, N- (2-chloro-4-methylphenyl) -N-methylcarbamoyloxy group, N- (2-methyl-3-fluoro) Phenyl) -N-methylcarbamoyloxy group, N- (2-trifluoromethylphenyl) -N-methylcarbamoyloxy group, N- (4-trifluoromethylphenyl) -N-methylcarbamoyloxy group, N-phenyl- N-phenylcarbamoyloxy group, N-phenyl-N- (2-fluorophenyl) carbamoyloxy group, -Phenyl-N- (3-fluorophenyl) carbamoyloxy group, N-phenyl-N- (4-fluorophenyl) carbamoyloxy group, N-phenyl-N- (2-chlorophenyl) carbamoyloxy group, N-phenyl- N- (3-chlorophenyl) carbamoyloxy group, N-phenyl-N- (4-chlorophenyl) carbamoyloxy group, N-phenyl-N- (2-bromophenyl) carbamoyloxy group, N-phenyl-N- (3) -Bromophenyl) carbamoyloxy group, N-phenyl-N- (4-bromophenyl) carbamoyloxy group, N-phenyl-N- (2-iodophenyl) carbamoyloxy group, N-phenyl-N- (3-iodo Phenyl) carbamoyloxy group, N-phenyl-N- (4-iodophenyl) group Bamoyloxy group, N-phenyl-N- (2,3-difluorophenyl) carbamoyloxy group, N-phenyl-N- (3,4-difluorophenyl) carbamoyloxy group, N-phenyl-N- (3,5-) Difluorophenyl) carbamoyloxy group, N-phenyl-N- (2,4-difluorophenyl) carbamoyloxy group, N-phenyl-N- (2,6-difluorophenyl) carbamoyloxy group, N-phenyl-N- ( 2,3-Dichlorophenyl) carbamoyloxy group, N-phenyl-N- (3,4-dichlorophenyl) carbamoyloxy group, N-phenyl-N- (3,5-dichlorophenyl) carbamoyloxy group, N-phenyl-N- (2,4-dichlorophenyl) carbamoyloxy group, N-phenyl-N- (2,6 -Dichlorophenyl) carbamoyloxy group, N-phenyl-N- (3,4,5-trifluorophenyl) carbamoyloxy group, N-phenyl-N- (3,4,5-trichlorophenyl) carbamoyloxy group, N- Phenyl-N- (2,4,6-trifluorophenyl) carbamoyloxy group, N-phenyl-N- (2,4,6-trichlorophenyl) carbamoyloxy group, N-phenyl-N- (2-methylphenyl) ) Carbamoyloxy group, N-phenyl-N- (3-methylphenyl) carbamoyloxy group, N-phenyl-N- (4-methylphenyl) carbamoyloxy group, N-phenyl-N- (2-methyl-3-) Chlorophenyl) carbamoyloxy group, N-phenyl-N- (3-methyl-4-chlorophenyl) carbamoyl Xy group, N-phenyl-N- (2-chloro-4-methylphenyl) carbamoyloxy group, N-phenyl-N- (2-methyl-3-fluorophenyl) carbamoyloxy group, N-phenyl-N- ( 2-trifluoromethylphenyl) carbamoyloxy group, N-phenyl-N- (3-trifluoromethylphenyl) carbamoyloxy group, N-phenyl-N- (4-trifluoromethylphenyl) carbamoyloxy group, 2-pentacene Fluoroethylphenylcarbamoyloxy group, 3-pentafluoroethylphenylcarbamoyloxy group, 4-pentafluoroethylphenylcarbamoyloxy group, 2-isopropylphenylcarbamoyloxy group, 3-isopropylphenylcarbamoyloxy group, 4-isopropylphenylcarba group Iryloxy group, 2-tert-butylphenylcarbamoyloxy group, 3-tert-butylphenylcarbamoyloxy group, 4-tert-butylphenylcarbamoyloxy group, 2-sec-butylphenylcarbamoyloxy group, 3-sec-butylphenylcarbamoyl group Oxy group, 4-sec-butylphenylcarbamoyloxy group, 2-n-heptafluoropropylphenylcarbamoyloxy group, 3-n-heptafluoropropylphenylcarbamoyloxy group, 4-n-heptafluoropropylphenylcarbamoyloxy group, 4 -N-pentylphenylcarbamoyloxy group, 4-n-hexylphenylcarbamoyloxy group, 2,4-dimethylphenylcarbamoyloxy group, 2,4,6-trimethylphenylcarbamoyl group Roxy group, 3,4-dimethoxyphenylcarbamoyloxy group, 3,4,5-trimethoxyphenylcarbamoyloxy group, 2-methoxyphenylcarbamoyloxy group, 3-methoxyphenylcarbamoyloxy group, 4-methoxyphenylcarbamoyloxy group, 2-methoxy-3-chlorophenylcarbamoyloxy group, 2-fluoro-3-methoxyphenylcarbamoyloxy group, 2-fluoro-4-methoxyphenylcarbamoyloxy group, 2,6-dimethoxyphenylcarbamoyloxy group, 2,3,4 -Trifluorophenylcarbamoyloxy group, 3,4,5-trifluorophenylcarbamoyloxy group, 2-trifluoromethoxyphenylcarbamoyloxy group, 3-trifluoromethoxyphenylcarbamoyloxy group , 4-trifluoromethoxyphenylcarbamoyloxy group, 2-pentafluoroethoxyphenylcarbamoyloxy group, 3-pentafluoroethoxyphenylcarbamoyloxy group, 4-pentafluoroethoxyphenylcarbamoyloxy group, 2-isopropoxyphenylcarbamoyloxy group, 3-isopropoxyphenylcarbamoyloxy group, 4-isopropoxyphenylcarbamoyloxy group, 2-tert-butoxyphenylcarbamoyloxy group, 3-tert-butoxyphenylcarbamoyloxy group, 4-tert-butoxyphenylcarbamoyloxy group, 2- sec-butoxyphenylcarbamoyloxy group, 3-sec-butoxyphenylcarbamoyloxy group, 4-sec-butoxyphenylcarbamoyl Xy group, 2-n-heptafluoropropoxyphenyl carbamoyloxy group, 3-n-heptafluoropropoxyphenyl carbamoyloxy group, 4-n-heptafluoropropoxyphenyl carbamoyloxy group, 4-n-pentyloxyphenyl carbamoyloxy group, A carbamoyloxy group such as a 4-n-hexyloxyphenylcarbamoyloxy group (a C1-6 alkyl group on the amino group and a phenyl group [a halogen atom or a halogen substituted or unsubstituted C1-6 alkyl on the phenyl ring 1 to 5, preferably 1 to 3 groups selected from the group consisting of groups and halogen-substituted or unsubstituted C1-6 alkoxy groups] may be selected from the group consisting of To 2) may be mentioned.

  Examples of the halogen-substituted or unsubstituted C1-10 alkyl group include, in addition to the halogen-substituted or unsubstituted C1-6 alkyl group, a heptyl group, an octyl group, a nonyl group, a decyl group and a 7-fluoroheptyl group. 7,7,6-trifluoroheptyl group, 7,7,7,6,6,5,5-heptafluoroheptyl group, 8-chlorooctyl group, 8,8-dibromooctyl group, 6,7 , 8-trifluorooctyl group, 8,8,8,7,7,6,6- heptafluorooctyl group, 8,8,8,7,7-pentachlorooctyl group, 9-iodononyl group, 9, 9-dibromononyl group, 9,9,9,8,8-pentachlorononyl group, 9,9,9,8,8,7,7-heptafluorononyl group, 10-chlorodecyl group, 10,10-dibromo Decyl group, 10, 10, 10, C1-10 alkyl groups such as tetrachlorodecyl group, 10, 10, 10, 9, 9, 9, 8, 8 heptafluorodecyl group and C1-10 alkyl groups substituted by 1 to 7 halogen atoms It can be mentioned.

  Phenyl group [in the phenyl ring, C1-4 alkylenedioxy group, cyano group, phenoxy group, C1-6 alkylthio group, C1-6 alkanoyl group, phenyl group, phenyl C1-6 alkyl group, halogen atom, halogen substitution Or at least one of a group selected from the group consisting of an unsubstituted C1-10 alkyl group and a halogen-substituted or unsubstituted C1-10 alkoxy group] is, for example, a phenyl group (phenyl At least one selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted on the ring And 4-cyanophenyl, 3-cyanophenyl, 2-cyanophenyl and 3,4-dicycyl. Nophenyl group, 3,4,5-tricyanophenyl group, 4-phenoxyphenyl group, 3-phenoxyphenyl group, 2-phenoxyphenyl group, 3,4-diphenoxyphenyl group, 2,4,6-triphenoxyphenyl group Group, 4-methylthiophenyl group, 3-methylthiophenyl group, 2-methylthiophenyl group, 3,4-dimethylthiophenyl group, 2,4,6-trimethylthiophenyl group, 4-acetylphenyl group, 3-acetylphenyl group Group, 2-acetylphenyl group, 3,4-diacetylphenyl group, 2,4,6-triacetylphenyl group, 4-biphenyl group, 3-biphenyl group, 2-biphenyl group, 3,4-diphenylphenyl group, 2,4,6-triphenylphenyl group, 4-heptyloxyphenyl group, 3-octyloxyphenyl group, 2 Nonyloxyphenyl group, 4-decyloxyphenyl group, 2,4-diheptyloxyphenyl group, 2,4,6-triheptyloxyphenyl group, 4- (7,7-dichloroheptyloxy) phenyl group, 4- Benzylphenyl group, 3-benzylphenyl group, 2-benzylphenyl group, 2,4-dibenzylphenyl group, 2,4,6-tribenzylphenyl group, 4-octylphenyl group, 4-heptylphenyl group, 3- Octylphenyl, 3- (8,8,8-trifluorooctyl) phenyl, 2-nonylphenyl, 4-decylphenyl, 2,4-dioctylphenyl, 2,4,6-trioctylphenyl Group, 4-phenyl-3-chlorophenyl group, 4-phenoxy-3-methylthiophenyl group, 4-heptyloxy-3-trifluoro Phenyl group such as lomethoxyphenyl group, 4-octyl-2-trifluoromethylphenyl group, 4-benzyl-2-methylphenyl group, 3,4-ethylenedioxyphenyl group, 3,4-methylenedioxyphenyl group [In the phenyl ring, C 1 -4 alkylenedioxy group, cyano group, phenoxy group, C1-6 alkylthio group, C1-6 alkanoyl group, phenyl group, phenyl C1-6 alkyl group, halogen atom, halogen substituted or not One to five, preferably one to three, groups selected from the group consisting of a substituted C1-10 alkyl group and a halogen substituted or unsubstituted C1-10 alkoxy group may be substituted (the substituent is C1 In the case of -4 alkylenedioxy group, one to two substituents may be substituted)].

A carbamoyloxy substituted C1-6 alkyl group (on the amino group, a C1-6 alkyl group, a phenyl C1-6 alkyl group, a C3-8 cycloalkyl group, a naphthyl group, a 2,3-dihydro-1H-indenyl group, 2 [1, 3-dihydrobenzofuryl group and phenyl group [on the phenyl ring, C1-4 alkylenedioxy group, cyano group, phenoxy group, C1-6 alkylthio group, C1-6 alkanoyl group, phenyl group, phenyl C1-6 At least one group selected from the group consisting of an alkyl group, a halogen atom, a halogen substituted or unsubstituted C1-10 alkyl group and a halogen substituted or unsubstituted C1-10 alkoxy group may be substituted As at least one group selected from the group consisting of: a carbamoyloxymethyl group, -Carbamoyloxyethyl group, 1-carbamoyloxyethyl group, 3-carbamoyloxypropyl group, 4-carbamoyloxybutyl group, 5-carbamoyloxypentyl group, 6-carbamoyloxyhexyl group, phenylcarbamoyloxymethyl group, 2-methyl Phenylcarbamoyloxymethyl group, 3-methylphenylcarbamoyloxymethyl group, 4-methylphenylcarbamoyloxymethyl group, 2,3-dimethylphenylcarbamoyloxymethyl group, 2,4-dimethylphenylcarbamoyloxymethyl group, 2, 6- Dimethylphenylcarbamoyloxymethyl group, 2,4,6-trimethylphenylcarbamoyloxymethyl group, 2-trifluoromethylphenylcarbamoyloxymethyl group, 3-trifluoromethyl Phenylcarbamoyloxymethyl group, 4-trifluoromethylphenylcarbamoyloxymethyl group, 2,3-ditrifluoromethylphenylcarbamoyloxymethyl group, 2,4-ditrifluoromethylphenylcarbamoyloxymethyl group, 2,6-ditrifluoromethyl Phenylcarbamoyloxymethyl group, 2-pentafluoroethylphenylcarbamoyloxymethyl group, 3-pentafluoroethylphenylcarbamoyloxymethyl group, 4-pentafluoroethylphenylcarbamoyloxymethyl group, 2- (n-propylphenyl) carbamoyloxymethyl group Group, 3- (n-propylphenyl) carbamoyloxymethyl group, 4- (n-propylphenyl) carbamoyloxymethyl group, 2- (phenylcarbamoyloxy) group Ethyl group, 2- (3-trifluoromethylphenylcarbamoyloxy) ethyl group, 2- (4-trifluoromethylphenylcarbamoyloxy) ethyl group, 2- (2,3-ditrifluoromethylphenylcarbamoyloxy) ethyl group, 2- (2,4-ditrifluoromethylphenylcarbamoyloxy) ethyl group, 2- (2,6-ditrifluoromethylphenylcarbamoyloxy) ethyl group, 2- (2-pentafluoroethylphenylcarbamoyloxy) ethyl group, 2 -(3-pentafluoroethylphenylcarbamoyloxy) ethyl group, 2- (4-pentafluoroethylphenylcarbamoyloxy) ethyl group, 3- (phenylcarbamoyloxy) propyl group, 3- (3-trifluoromethylphenylcarbamoyloxy) ) Pill, 3- (4-trifluoromethylphenylcarbamoyloxy) propyl, 3- (2,3-ditrifluoromethylphenylcarbamoyloxy) propyl, 3- (2,4-ditrifluoromethylphenylcarbamoyloxy) propyl Group, 3- (2,6-ditrifluoromethylphenylcarbamoyloxy) propyl group, 3- (2-pentafluoroethylphenylcarbamoyloxy) propyl group, 3- (3-pentafluoroethylphenylcarbamoyloxy) propyl group, 3 -(4-Pentafluoroethylphenylcarbamoyloxy) propyl group, 4- (4-trifluoromethylphenylcarbamoyloxy) butyl group, 5- (4-trifluoromethylphenylcarbamoyloxy) pentyl group, 6- (4-trichlorophenyl) Fluoro Ethylphenylcarbamoyloxy) hexyl group, (2-fluorophenylcarbamoyloxy) methyl group, 2- (3-fluorophenylcarbamoyloxy) ethyl group, 1- (4-fluorophenylcarbamoyloxy) ethyl group, 3- (2- (2-fluorophenylcarbamoyloxy) ethyl group Chlorophenylcarbamoyloxy) propyl group, 4- (3-chlorophenylcarbamoyloxy) butyl group, 5- (4-chlorophenylcarbamoyloxy) pentyl group, 6- (2-bromophenylcarbamoyloxy) hexyl group, (3-bromophenylcarbamoyl Oxy) methyl group, 2- (4-bromophenylcarbamoyloxy) ethyl group, 1- (2-iodophenylcarbamoyloxy) ethyl group, 3- (3-iodophenylcarbamoyloxy) propyl group, 4- (4-iodopheny Carbamoyloxy) butyl group, 5- (2,3-difluorophenylcarbamoyloxy) pentyl group, 6- (3,4-difluorophenylcarbamoyloxy) hexyl group, (3,5-difluorophenylcarbamoyloxy) methyl group, 2 -(2,4-difluorophenylcarbamoyloxy) ethyl group, 1- (2,6-difluorophenylcarbamoyloxy) ethyl group, 3- (2,3-dichlorophenylcarbamoyloxy) propyl group, 4- (3,4-) Dichlorophenylcarbamoyloxy) butyl group, 5- (3,5-dichlorophenylcarbamoyloxy) pentyl group, 6- (2,4-dichlorophenylcarbamoyloxy) hexyl group, (2,6-dichlorophenylcarbamoyloxy) methyl group, 2- ( 3,4,5-Tri Fluorophenylcarbamoyloxy) ethyl group, 1- (2,3,4,5,6-pentafluorophenylcarbamoyloxy) ethyl group, 3- (3,4,5-trichlorophenylcarbamoyloxy) propyl group, 4- (2,4,6-trifluorophenylcarbamoyloxy) butyl group, 5- (2,4,6-trichlorophenylcarbamoyloxy) pentyl group, (2-methyl-3-chlorophenylcarbamoyloxy) methyl group, (3- Methyl-4-chlorophenylcarbamoyloxy) methyl group, (2-chloro-4-methylphenylcarbamoyloxy) methyl group, (2-methyl-3-fluorophenylcarbamoyloxy) methyl group, ethylcarbamoyloxymethyl group, n-butyl Rucarbamoyloxymethyl group, n-hexyl cal Moyloxymethyl group, n-pentylcarbamoyloxymethyl group, N-methyl-N-phenylcarbamoyloxymethyl group, N, N-dimethylcarbamoyloxymethyl group, N-methyl-N-ethylcarbamoyloxymethyl group, 2- [ N- (2-fluorophenyl) -N-methylcarbamoyloxy] ethyl group, 1- [N- (3-fluorophenyl) -N-methylcarbamoyloxy] ethyl group, 3- [N- (4-fluorophenyl) group -N-methylcarbamoyloxy] propyl group, 4- [N- (2-chlorophenyl) -N-methylcarbamoyloxy] butyl group, 5- [N- (3-chlorophenyl) -N-methylcarbamoyloxy] pentyl group, 6- [N- (4-chlorophenyl) -N-methylcarbamoyloxy] hexyl group, [6 N- (4-bromophenyl) -N-methylcarbamoyloxy] methyl group, 2- [N- (2-iodophenyl) -N-methylcarbamoyloxy] ethyl group, 1- [N- (3-iodophenyl) group -N-methylcarbamoyloxy] ethyl group, 3- [N- (4-iodophenyl) -N-methylcarbamoyloxy] propyl group, 4- [N- (2,3-difluorophenyl) -N-methylcarbamoyloxy Butyl group, 5- [N- (3,4-difluorophenyl) -N-methylcarbamoyloxy] pentyl group, 6- [N- (3,5-difluorophenyl) -N-methylcarbamoyloxy] hexyl group, [N- (2,4-difluorophenyl) -N-methylcarbamoyloxy] methyl group, 2- [N- (2,6-difluorophenyl) -N- Ethyl carbamoyloxy! Ethyl group, 1- [N- (2,3-dichlorophenyl) -N-methylcarbamoyloxy] ethyl group, 3- [N- (3,4-dichlorophenyl) -N-methylcarbamoyloxy] propyl group , [N- (3,5-dichlorophenyl) -N-methylcarbamoyloxy] methyl group, 4- [N- (2,4-dichlorophenyl) -N-methylcarbamoyloxy] butyl group, 5- [N- (2) , 6-Dichlorophenyl) -N-methylcarbamoyloxy] pentyl group, 6- [N- (3,4,5-trifluorophenyl) -N-methylcarbamoyloxy] hexyl group, [N- (3,4,5 -Trichlorophenyl) -N-methylcarbamoyloxy] methyl group, 2- [N- (2,4,6-trifluorophenyl) -N-methyl Rubamoyloxy] ethyl group, 1- [N- (2,4,6-trichlorophenyl) -N-methylcarbamoyloxy] ethyl group, 3- [N- (2-methylphenyl) -N-methylcarbamoyloxy] propyl group , 4- [N- (3-methylphenyl) -N-methylcarbamoyloxy] butyl group, 5- [N- (4-methylphenyl) -N-methylcarbamoyloxy] hexyl group, 6- [N- (2) -Methyl-3-chlorophenyl) -N-methylcarbamoyloxy] hexyl group, [N- (3-methyl-4-chlorophenyl) -N-methylcarbamoyloxy] methyl group, 2- [N- (2-chloro-4) -Methylphenyl) -N-methylcarbamoyloxy] ethyl group, 1- [N- (2-methyl-3-fluorophenyl) -N-methylcarbamoyl Oxy] ethyl group, 3- [N- (2-trifluoromethylphenyl) -N-methylcarbamoyloxy] propyl group, 4- [N- (4-trifluoromethylphenyl) -N-methylcarbamoyloxy] butyl group , 2- [N- (4-trifluoromethylphenyl) -N-methylcarbamoyloxy] ethyl group, 5- [N-phenyl-N-phenylcarbamoyloxy] pentyl group, 6- [N-phenyl-N- ( 2-fluorophenyl) carbamoyloxy] hexyl group, [N-phenyl-N- (3-fluorophenyl) carbamoyloxy] methyl group, 2- [N-phenyl-N- (4-fluorophenyl) carbamoyloxy] ethyl group 1- [N-phenyl-N- (2-chlorophenyl) carbamoyloxy] ethyl group, 1- [N-pheny -N- (3-chlorophenyl) carbamoyloxy] ethyl group, 3- [N-phenyl-N- (4-chlorophenyl) carbamoyloxy] propyl group, 4- [N-phenyl-N- (2-bromophenyl) carbamoyl Oxy] butyl group, 5- [N-phenyl-N- (3-bromophenyl) carbamoyloxy] pentyl group, 6- [N-phenyl-N- (4-bromophenyl) carbamoyloxy] hexyl group, [N- Phenyl-N- (2-iodophenyl) carbamoyloxy] methyl group, 1- [N-phenyl-N- (3-iodophenyl) carbamoyloxy] ethyl group, 2- [N-phenyl-N- (4-iodo) Phenyl) carbamoyloxy] ethyl group, 1- [N-phenyl-N- (2,3-difluorophenyl) carbamoyloxy Ethyl group, 3- [N-phenyl-N- (3,4-difluorophenyl) carbamoyloxy] propyl group, 4- [N-phenyl-N- (3,5-difluorophenyl) carbamoyloxy] butyl group, 5 -[N-phenyl-N- (2,4-difluorophenyl) carbamoyloxy] pentyl group, 6- [N-phenyl-N- (2,6-difluorophenyl) carbamoyloxy] hexyl group, [N-phenyl- N- (2,3-dichlorophenyl) carbamoyloxy] methyl group, 2- [N-phenyl-N- (3,4-dichlorophenyl) carbamoyloxy] ethyl group, 1- [N-phenyl-N- (3,5) -Dichlorophenyl) carbamoyloxy] ethyl group, 3- [N-phenyl-N- (2,4-dichlorophenyl) carbamoyloxy] Propyl group, 4- [N-phenyl-N- (2,6-dichlorophenyl) carbamoyloxy] butyl group, 5- [N-phenyl-N- (3,4,5-trifluorophenyl) carbamoyloxy] pentyl group , 6- [N-phenyl-N- (3,4,5-trichloropheny


Carbamoyloxy! Hexyl group, [N-phenyl-N- (2,4,6-trifluorophenyl) carbamoyloxy] methyl group, 2- [N-phenyl-N- (2,4,6-trichlorophenyl] 4) carbamoyloxy] ethyl group, 1- [N-phenyl-N- (2-methylphenyl) carbamoyloxy] ethyl group, 3- [N-phenyl-N- (3-methylphenyl) carbamoyloxy] propyl group, 4 -[N-phenyl-N- (4-methylphenyl) carbamoyloxy] butyl group, 5- [N-phenyl-N- (2-methyl-3-chlorophenyl) carbamoyloxy] pentyl group, 6- [N-phenyl group -N- (3-methyl-4-chlorophenyl) carbamoyloxy] hexyl group, [N-phenyl-N- (2-chloro-4-methyl) Group) carbamoyloxy! Methyl group, [N-phenyl-N- (2-methyl-3-fluorophenyl) carbamoyloxy] methyl group, 2- [N-phenyl-N- (2-trifluoromethylphenyl) carbamoyloxy] Ethyl group, 1- [N-phenyl-N- (3-trifluoromethylphenyl) carbamoyloxy] ethyl group, 3- [N-phenyl-N- (4-trifluoromethylphenyl) carbamoyloxy] propyl group, 2-isopropylphenylcarbamoyloxymethyl group, 3-isopropylphenylcarbamoyloxymethyl group, 4-isopropylphenylcarbamoyloxymethyl group, 2-tert-butylphenylcarbamoyloxymethyl group, 4-n-butylphenylcarbamoyloxymethyl group, 2 -Methyl-4 Chlorophenylcarbamoyloxymethyl group, 3-tert-butylphenylcarbamoyloxymethyl group, 4-tert-butylphenylcarbamoyloxymethyl group, 2-sec-butylphenylcarbamoyloxymethyl group, 3-sec-butylphenylcarbamoyloxymethyl group, 4-sec-butylphenylcarbamoyloxymethyl group, 4-pentylphenylcarbamoyloxymethyl group, 4-hexylphenylcarbamoyloxymethyl group, 3,4-dimethoxyphenylcarbamoyloxymethyl group, 3,4,5-trimethoxyphenylcarbamoyl Oxymethyl group, 2-methoxyphenylcarbamoyloxymethyl group, 3-methoxyphenylcarbamoyloxymethyl group, 4-methoxyphenylcarbamoyloxymethyl Group, 2-methoxy-3-chlorophenylcarbamoyloxymethyl group, 2- (2-fluoro-3-methoxyphenylcarbamoyloxy) ethyl group, 1- (2-fluoro-4-methoxyphenylcarbamoyloxy) ethyl group, 3- (2,6-dimethoxyphenylcarbamoyloxy) propyl group, 4- (2,3,4-trifluorophenylcarbamoyloxy) butyl group, 5- (3,4,5-trifluorophenylcarbamoyloxy) pentyl group, 6 -(2-trifluoromethoxyphenylcarbamoyloxy) hexyl group, 3-trifluoromethoxyphenylcarbamoyloxymethyl group, 4-trifluoromethoxyphenylcarbamoyloxymethyl group, 2- (4-trifluoromethoxyphenylcarbamoyloxy) ethyl group , 2 [N-methyl-N- (4-trifluoromethoxyphenyl) carbamoyloxy] ethyl group, 3-trifluoromethylphenylcarbamoyloxymethyl group, 4-trifluoromethylphenylcarbamoyloxymethyl group, 3-trifluoromethyl-4 -Chlorophenylcarbamoyloxymethyl group, 3,5-ditrifluoromethoxyphenylcarbamoyloxymethyl group, 2,4-dichlorophenylcarbamoyloxymethyl group, 2-chlorophenylcarbamoyloxymethyl group, 3-chlorophenylcarbamoyloxymethyl group, 4-chlorophenylcarbamoyl group Oxymethyl group, 3,5-dichlorophenylcarbamoyloxymethyl group, 3,4-dichlorophenylcarbamoyloxymethyl group, 2-fluorophenylcarbamoyloxy group Simethyl group, 3-fluorophenylcarbamoyloxymethyl group, 4-fluorophenylcarbamoyloxymethyl group, 2-pentafluoroethoxyphenylcarbamoyloxymethyl group, 3-pentafluoroethoxyphenylcarbamoyloxymethyl group, 4-pentafluoroethoxyphenylcarbamoyl group Oxymethyl group, 2-isopropoxyphenylcarbamoyloxymethyl group, 3-isopropoxyphenylcarbamoyloxymethyl group, 4-isopropoxyphenylcarbamoyloxymethyl group, 2-tert-butoxyphenylcarbamoyloxymethyl group, 4-n-butoxy Phenylcarbamoyloxymethyl group, 3-methoxyphenylcarbamoyloxymethyl group, 4-methoxyphenylcarbamoyloxymethyl group, 4- Ethoxyphenylcarbamoyloxymethyl group, 3-tert-butoxyphenylcarbamoyloxymethyl group, 4-tert-butoxyphenylcarbamoyloxymethyl group, 2-sec-butoxyphenylcarbamoyloxymethyl group, 3-sec-butoxyphenylcarbamoyloxymethyl group 4-sec-Butoxyphenylcarbamoyloxymethyl group, 2-n-heptafluoropropoxyphenylcarbamoyloxymethyl group, 3-n-heptafluoropropoxyphenylcarbamoyloxymethyl group, 4-n-heptafluoropropoxyphenylcarbamoyloxymethyl group , 4-n-pentyloxyphenylcarbamoyloxymethyl group, 4-n-hexyloxyphenylcarbamoyloxymethyl group, 4-cyanophenyl Rubamoyloxymethyl group, [N-methyl-N- (3-cyanophenyl) carbamoyloxy] methyl group, 2-cyanophenylcarbamoyloxymethyl group, 3,4-dicyanophenylcarbamoyloxymethyl group, 3, 4, 5 -Tricyanophenylcarbamoyloxymethyl group, 4-phenoxyphenylcarbamoyloxymethyl group, [N-methyl-N- (3-phenoxyphenyl) carbamoyloxy] methyl group, 2-phenoxyphenylcarbamoyloxymethyl group, 3,4- Diphenoxyphenylcarbamoyloxymethyl group, 2,4,6-triphenoxyphenylcarbamoyloxymethyl group, 4-methylthiophenylcarbamoyloxymethyl group, [N-methyl-N- (4-methylthiophenyl) carbamoyloxy] methyl , 3-methylthiophenylcarbamoyloxymethyl group, 2-methylthiophenylcarbamoyloxymethyl group, 3,4-dimethylthiophenylcarbamoyloxymethyl group, 2,4,6-trimethylthiophenylcarbamoyloxymethyl group, 4-acetylphenylcarbamoyl group Oxymethyl group, 3-acetylphenylcarbamoyloxymethyl group, 2-acetylphenylcarbamoyloxymethyl group, 3,4-diacetylphenylcarbamoyloxymethyl group, [N-methyl-N- (3,4-diacetylphenyl) carbamoyloxy group Methyl group, 2,4,6-triacetylphenylcarbamoyloxymethyl group, 4-biphenylcarbamoyloxymethyl group, 3-biphenylcarbamoyloxymethyl group, 2-biphenylcarbamoyl group Oxymethyl group, [N-methyl-N- (2-biphenyl) carbamoyloxy] methyl group, 3,4-diphenylphenylcarbamoyloxymethyl group, 2,4,6-triphenylphenylcarbamoyloxymethyl group, 4-n -Heptyloxyphenylcarbamoyloxymethyl group, [N-methyl-N-4- (n-heptyloxyphenyl) carbamoyloxy] methyl group, 3-n-octyloxyphenylcarbamoyloxymethyl group, 2-n-nonyloxyphenyl group Carbamoyloxymethyl group, 4-n-decyloxyphenylcarbamoyloxymethyl group, 2,4-di n-heptyloxyphenylcarbamoyloxymethyl group, 2,4,6-tri n-heptyloxyphenylcarbamoyloxymethyl group, 4 -(7,7-dichlorohept Roxy) phenylcarbamoyloxymethyl group, 4-benzylphenylcarbamoyloxymethyl group, [N-methyl-N- (4-benzylphenyl) carbamoyloxy] methyl group, 3-benzylphenylcarbamoyloxymethyl group, 2-benzylphenylcarbamoyl group Oxymethyl group, 2,4-dibenzylphenylcarbamoyloxymethyl group, 2,4,6-tribenzylphenylcarbamoyloxymethyl group, 4-n-octylphenylcarbamoyloxymethyl group, [N-methyl-N- (4) -N-octylphenyl) carbamoyloxy] methyl group, 3-n-heptylphenylcarbamoyloxymethyl group, 2-n-octylphenylcarbamoyloxymethyl group, 3- (8,8,8-trifluorooctyl) phenylcarbamomo group Roxymethyl group, 4-n-nonylphenylcarbamoyloxymethyl group, 3-n-decylphenylcarbamoyloxymethyl group, 2,4-di n-octylphenylcarbamoyloxymethyl group, 2,4,6-tri-n-octylsilyl group Phenylcarbamoyloxymethyl group, 4-phenyl-3-chlorophenylcarbamoyloxymethyl group, 4-phenoxy-3-methylthiophenylcarbamoyloxymethyl group, 4-n-heptyloxy-3-trifluoromethoxyphenylcarbamoyloxymethyl group, 4 -N-octyl-2-trifluoromethylphenylcarbamoyloxymethyl group, 4-benzyl-2-methylphenylcarbamoyloxymethyl group, 3,4-ethylenedioxyphenylcarbamoyloxymethyl group, 3,4-methylenedi Oxyphenylcarbamoyloxymethyl group, benzylcarbamoyloxymethyl group, 2-phenylethylcarbamoyloxymethyl group, cyclohexylcarbamoyloxymethyl group, 1-naphthylcarbamoyloxymethyl group, 2-naphthylcarbamoyloxymethyl group, 5- (2,3 -Dihydro-1H-indenyl) carbamoyloxymethyl group, 5- (2,3-dihydrobenzofuryl) carbamoyloxymethyl group, [N-methyl-N- (3,4-methylenedioxyphenyl) carbamoyloxy] methyl group , (N-methyl-N-benzylcarbamoyloxy) methyl group, [N-methyl-N- (2-phenylethyl) carbamoyloxy] methyl group, (N-methyl-N-cyclohexylcarbamoyloxy) methyl group, [N -Methyl- -(1-naphthyl) carbamoyloxy] methyl group, [N-methyl-N- (2-naphthyl) carbamoyloxy] methyl group, {N-methyl-N- [5- (2,3-dihydro-1H-indenyl) ) Carbamoyloxy substituted C1-6 alkyl groups such as [N-methyl-N- (2,3-dihydro-5-benzofuryl) carbamoyloxy] methyl group, etc. (on the amino group, C1 -C6) 6 alkyl group, phenyl C1-6 alkyl group described above, C3-8 cycloalkyl group described above, naphthyl group, 2,3-dihydro-1H-indenyl group, 2,3-dihydrobenzofuryl group and the above Phenyl group [in the phenyl ring, C1 -4 alkylenedioxy group, cyano group, phenoxy group, C1-6 alkylthio group, C1-6 alkano A group selected from the group consisting of alkyl group, phenyl group, phenyl C1-6 alkyl group, halogen atom, halogen substituted or unsubstituted C1-10 alkyl group and halogen substituted or unsubstituted C1-10 alkoxy group 5 or preferably 1 to 3 (or 1 to 2 substituted when the substituent is a C1 to 4 alkylenedioxy group may be substituted) is selected from the group consisting of And the group may be substituted by 1 to 2).

  As a C1-6 alkanoyl substituted C1-6 alkyl group, for example, acetylmethyl group, 2-propionylethyl group, 1-butyrylethyl group, 2-acetylethyl group, 3-acetylpropyl group, 4-acetylbutyl group, 4- Isobutyrylbutyl, 5-pentanoylpentyl, 6-acetylhexyl, 6-tert-butylcarbonylhexyl, 1,1-dimethyl-2-hexanoylethyl, 2-methyl-3-acetylpropyl Etc. can be mentioned.

Phenoxy C1-6 alkyl group (a halogen atom on the phenyl ring; C1 -4 alkylenedioxy group; C1 to 6 alkoxycarbonyl group; phenyl group; phenoxy group; pyrrolyl group; benzothiazolyl group; 1,2,4 triazolyl Group: imidazolyl group; isoxazolyl group; benzoxazolyl group; benzotriazolyl group; cyano group; nitro group; C2-6 alkenyl group; C1-6 alkanoyl group; C1-6 alkoxycarbonyl substituted C1-6 alkyl group; C1-6 alkanoyl substituted C1-6 alkyl group; group -N ( ^{R11B '} ) ^R12B' ( ^{R11B '} and ^R12B' are the same or different and are a hydrogen atom, C1-6 alkyl group, C1-6 alkanoyl group or .R ^{11B 'and} R ^12B' represents a phenyl group, through together with the adjacent nitrogen atom, a nitrogen atom, an oxygen atom or a sulfur atom Alternatively, they may be combined with each other to form a 5- to 7-membered saturated heterocyclic ring on which a C1-6 alkoxycarbonyl group and an amino group [phenyl group (phenyl group At least one selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted on the ring And at least one group selected from the group consisting of C.sub.1-6 alkyl groups may optionally be substituted); phenyl C1 -6 alkoxy group; phenyl C1-6 alkyl group; C1-6 alkylthio group; C3-8 cycloalkyl group; halogen substituted or unsubstituted C1-6 alkyl group and halogen substituted or unsubstituted And at least one group selected from the group consisting of a C.sub.1-10 alkoxy group may be substituted). As the phenoxy C1-6 alkyl group (on the phenyl ring, it is selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group) 3,4-methylenedioxyphenoxymethyl group, 3,4-ethylenedioxyphenoxymethyl group, 4-ethoxycarbonylphenoxymethyl group, in addition to -Methoxycarbonylphenoxymethyl group, 2-ethoxycarbonylphenoxymethyl group, 2,4-diethoxycarbonylphenoxymethyl group, 2,4,6-triethoxycarbonylphenoxymethyl group, 2-ethoxycarbonyl-4-methylphenoxymethyl group , 2-Methoxycarbonyl-4-methoxyphenoxymethyl , 2-methoxycarbonyl-3-methoxyphenoxymethyl group, 2- (4-ethoxycarbonylphenoxy) ethyl group, 4-cyanophenoxymethyl group, 3-cyanophenoxymethyl group, 2-cyanophenoxymethyl group, 2,4- Dicyanophenoxymethyl group, 2,4,6-tricyanophenoxymethyl group, 2- (4-cyanophenoxy) ethyl group, 4-nitrophenoxymethyl group, 3-nitrophenoxymethyl group, 2-nitrophenoxymethyl group, 2 , 4-Dinitrophenoxymethyl group, 2,4,6-trinitrophenoxymethyl group, 2- (4-nitrophenoxy) ethyl group, 4-allylphenoxymethyl group, 3-allylphenoxymethyl group, 2-allylphenoxymethyl group Group, 3,4-diallylphenoxymethyl group, 3,4,5-tria 2-phenoxy-ethyl group, 2- (3-allylphenoxy) ethyl group, 3-diethylaminophenoxymethyl group, 3-anilininophenoxymethyl group, 4-acetylaminophenoxymethyl group, 2,4,6-tri (diethylamino) phenoxymethyl group, 2-anilinophenoxymethyl group, 2,4-diacetylaminophenoxymethyl group, 2- (3-diethylaminophenoxy) ethyl group, 2- (3-anilino Phenoxy) ethyl group, 2- [4- (2-acetylethyl) phenoxy] ethyl group, 4- (2-acetylethyl) phenoxymethyl group, 3-acetylmethylphenoxymethyl group, 2- (3-acetylpropyl) phenoxy Methyl, 2,4-di (2-acetylethyl) phenoxymethyl, 2,4 , 6-tri (2- acetyl ethyl) phenoxy methyl group, 4- methoxy carbonyl methyl phenoxy methyl group, 3- ethoxy carbonyl methyl phenoxy methyl group, 2- methoxy carbonyl methyl phenoxy methyl group, 2, 4- dimethoxy carbonyl methyl phenoxy methyl Group, 2,4,6-trimethoxycarbonylmethylphenoxymethyl group, 2- (4-methoxycarbonylmethylphenoxy) ethyl group, 4-propionylphenoxymethyl group, 4-acetylphenoxymethyl group, 3-propionylphenoxymethyl group, 2-acetylphenoxymethyl group, 2,4-dipropionylphenoxymethyl group, 2,4,6-triacetylphenoxymethyl group, 2- (4-propionylphenoxy) ethyl group, 2-benzylphenoxymethyl group, 3 Benzylphenoxymethyl group, 4-benzylphenoxymethyl group, 2,3-dibenzylphenoxymethyl group, 3,4,5-tribenzylphenoxymethyl group, 4-methylthiophenoxymethyl group, 3-methylthiophenoxymethyl group, 2- Methylthiophenoxymethyl group, 2,4-dimethylthiophenoxymethyl group, 2,4,6-trimethylthiophenoxymethyl group, 2- (4-methylthiophenoxy) ethyl group, 4-cyclopentylphenoxymethyl group, 3-cyclohexylphenoxymethyl Group, 4-cyclohexylphenoxymethyl group, 2-cycloheptylphenoxymethyl group, 2,4-dicyclopentylphenoxymethyl group, 2,4-cyclopentyl-6-cyclooctylphenoxymethyl group, 2- (4-cyclohexylphenoxy group Ethyl group, 2- (4-cyclopentylphenoxy) ethyl group, 4-n-octyloxyphenoxymethyl group, 2- (4-n-octyloxyphenoxy) ethyl group, 4-phenylphenoxymethyl group, 3-phenylphenoxymethyl Group, 2-phenylphenoxymethyl group, 2,4-diphenylphenoxymethyl group, 2,4,6-triphenylphenoxymethyl group, 2- (4-phenylphenoxy) ethyl group, 4-phenoxyphenoxymethyl group, 3- Phenoxyphenoxymethyl group, 2-phenoxyphenoxymethyl group, 2,4-diphenoxyphenoxymethyl group, 2,4,6-triphenoxyphenoxymethyl group, 2- (3-phenoxyphenoxy) ethyl group, 4-benzyloxyphenoxy Methyl group, 3-benzyloxyphenoxymeth Group, 2-benzyloxyphenoxymethyl group, 2,4-dibenzyloxyphenoxymethyl group, 2,4,6-tribenzyloxyphenoxymethyl group, 2- (4-benzyloxyphenoxy) ethyl group, 2,4 -Dibenzylphenoxymethyl group, 2,4,6-tribenzylphenoxymethyl group, 2- (4-benzylphenoxy) ethyl group, 4- (1-pyrrolyl) phenoxymethyl group, 3- (1-pyrrolyl) phenoxymethyl Group, 2- (1-pyrrolyl) phenoxymethyl group, 2,4-di (1-pyrrolyl) phenoxymethyl group, 2,4,6-tri (1-pyrrolyl) phenoxymethyl group, 2- (2-benzothiazolyl) Phenoxymethyl group, 2- (2-benzothiazolyl) phenoxymethyl group, 3- (2-benzothiazolyl) phenoxymethyl group 2,4,6-tri (5-benzothiazolyl) phenoxymethyl group, 2,4-di (6-benzothiazolyl) phenoxymethyl group, 4- (1-1,2,4-triazolyl) phenoxymethyl group, 3- ( 1-1,2,4-triazolyl) phenoxymethyl group, 2- (1-1,2,4-triazolyl) phenoxymethyl group, 4- (3-1,2,4-triazolyl) phenoxymethyl group, 2, 4-di (5-1,2,4-triazolyl) phenoxymethyl group, 2,4,6-tri (1-1,2,4-triazolyl) phenoxymethyl group, 4- (5-isoxazolyl) phenoxymethyl group , 3- (3-isoxazolyl) phenoxymethyl group, 2- (4-isoxazolyl) phenoxymethyl group, 2- (5-isoxazolyl) phenoxymethyl group, 2, -Di (5-isoxazolyl) phenoxymethyl group, 2,4,6-tri (5-isoxazolyl) phenoxymethyl group, 4- (1-imidazolyl) phenoxymethyl group, 3- (2-imidazolyl) phenoxymethyl group, 2 -(4-Imidazolyl) phenoxymethyl group, 2,4-di (1-imidazolyl) phenoxymethyl group, 2,4,6-tri (1-imidazolyl) phenoxymethyl group, 4- (1-benzotriazolyl) Phenoxymethyl group, 3- (1-benzotriazolyl) phenoxymethyl group, 2- (1-benzotriazolyl) phenoxymethyl group, 2- (1-benzotriazolyl) phenoxymethyl group, 2,4- Di (1-benzotriazolyl) phenoxymethyl group, 2,4,6-tri (1-benzotriazolyl) phenoxymethyl group, 4 -(6-benzoimidazolyl) phenoxymethyl group, 3- (5-benzoimidazolyl) phenoxymethyl group, 2- (2-benzoimidazolyl) phenoxymethyl group, 2- (1-benzotriazolyl) phenoxymethyl group, 2,4- Di (2-benzoimidazolyl) phenoxymethyl group, 2,4,6-tri (2-benzoimidazolyl) phenoxymethyl group, 4- (4-tert-butoxycarbonyl-1-piperazinyl) phenoxymethyl group, 2- [4-{{ 4- [4- (N- (4-chlorophenyl) -N-methylamino)]-1-piperidyl} phenoxy] ethyl group, 2- [4- (1-1,2,4-triazolyl) phenoxy] ethyl group , 2- [2- (5-isoxazolyl) phenoxy] ethyl group, 2- (2-methoxy-4-allylphenoxy) Ethyl group, 2- (2-fluoro-4-nitrophenoxy) ethyl group, 2- (2-ethoxy-5-allylphenoxy) ethyl group, 2-fluoro-4-nitrophenoxymethyl group, 2-methoxy-4- Phenoxy C1-6 alkyl groups such as allyl phenoxy methyl group, 2-ethoxy-5-allyl phenoxy methyl group, 2-methyl-4- acetyl phenoxy methyl group (on the phenyl ring, halogen atoms; C1 -4 alkylenedioxy Group: C1-6 alkoxycarbonyl group; phenyl group; phenoxy group; pyrrolyl group; benzothiazolyl group; 1,2,4-triazolyl group; imidazolyl group; isoxazolyl group; benzoxazolyl group; benzotriazolyl group; cyano group Nitro group; C2-6 alkenyl group; C1-6 alkanoyl group; C1-6 alkoxy Carbonyl-substituted Cl to 6 alkyl radical; Cl to 6 alkanoyl substituted Cl to 6 alkyl radical; group ^{-N (R 11B ') R 12B} ' (R 11B ' and R ^12B' are the same or different and represent a hydrogen atom, Cl to 6 It shows an alkyl group, a C1-6 alkanoyl group or a phenyl group. R ^{11B ′} and R ^{12B ′} may be combined with adjacent nitrogen atoms with each other with or without a nitrogen atom, an oxygen atom or a sulfur atom to form a 5- to 7-membered saturated heterocyclic ring. On the hetero ring, a C 1 to 6 alkoxycarbonyl group and an amino group [on the amino group, a phenyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C 1 to 6 alkyl group and a halogen substituted or A group selected from the group consisting of 1 to 5, preferably 1 to 3 groups selected from the group consisting of unsubstituted C1-6 alkoxy groups) and a group consisting of C1 to 6 alkyl groups A group selected from the group consisting of one to two may be substituted, and one to three groups may be substituted); phenyl C1-6 alkoxy group; phenyl C1-6 alkyl group; C1-6 alkylthio Group: 1 to 5 groups, preferably 1 to 5 groups selected from the group consisting of C3-8 cycloalkyl groups; halogen substituted or unsubstituted C1-6 alkyl groups and halogen substituted or unsubstituted C1-10 alkoxy groups (If substituents are C1~4 alkylenedioxy group, it is preferable is one to two substituents) may also be individual substitutions are shown a). Can be mentioned.

  As a tetrahydropyranyloxy C1-6 alkyl group, for example, (2-tetrahydropyranyloxy) methyl group, 2- (3-tetrahydropyranyloxy) ethyl group, 1- (4-tetrahydropyranyloxy) ethyl group 2- (2-tetrahydropyranyloxy) ethyl group, 3- (2-tetrahydropyranyloxy) propyl group, 4- (2-tetrahydropyranyloxy) butyl group, 4- (3-tetrahydropyranyloxy) group Butyl group, 5- (2-tetrahydropyranyloxy) pentyl group, 6- (2-tetrahydropyranyloxy) hexyl group, 6- (2-tetrahydropyranyloxy) hexyl group, 1,1-dimethyl-2- (4-Tetrahydropyranyloxy) ethyl group, 2-methyl-3- (3-tetrahydropyranyloxy) pro It can be exemplified Le group.

  As the furyl C1-6 alkoxy substituted C1-6 alkyl group (on the furan ring, at least one C1-6 alkoxycarbonyl group may be substituted), for example, [(2-furyl) methoxy] methyl Group, [2- (3-furyl) ethoxy] methyl group, [3- (2-furyl) propoxy] methyl group, [2- (3-furyl) propoxy] methyl group, [4- (2-furyl) butoxy] Methyl group, [5- (3-furyl) pentoxy] methyl group, [4- (2-furyl) pentoxy] methyl group, [6- (3-furyl) hexyloxy] methyl group, 2- [(2- Furyl) methoxy] ethyl group, 1- [2- (3-furyl) ethoxy] ethyl group, 3- [3- (2-furyl) propoxy] propyl group, 4- [2- (3-furyl) propoxy] butyl Group, 5- [4 (2-furyl) butoxy] hexyl group, 1,1-dimethyl-2- [5- (3-furyl) pentoxy] ethyl group, 2-methyl-3- [4- (2-furyl) pentoxy] propyl group, 2- [6- (3-furyl) hexyloxy] ethyl group, [(5-ethoxycarbonyl-2-furyl) methoxy] methyl group, [(4-methoxycarbonyl-2-furyl) methoxy] methyl group, [( 3-propoxycarbonyl-2-furyl) methoxy] methyl group, [(5-butoxycarbonyl-2-furyl) methoxy] methyl group, [(4-pentyloxycarbonyl-2-furyl) methoxy] methyl group, [(3 -Hexyloxycarbonyl-2-furyl) methoxy] methyl group, [(3,5-diethoxycarbonyl-2-furyl) methoxy] methyl group, [(3,4,5 Furyl C1-6 alkoxy-substituted C1-6 alkyl group such as triethoxycarbonyl-2-furyl) methoxy] methyl group (1 to 3 C1-6 alkoxycarbonyl group may be substituted on the furan ring Can be mentioned.

  As a C3-8 cycloalkyl C1-6 alkyl group, for example, cyclohexylmethyl group, 2-cyclopropylethyl group, 1-cyclopentylethyl group, 3-cyclobutylpropyl group, 4-cyclohexylbutyl group, 5-cycloheptylpentyl Groups, 6-cyclooctylhexyl group, 1,1-dimethyl-2-cyclohexylethyl group, 2-methyl-3-cyclohexylpropyl group and the like.

  Tetrazolyl C.sub.1-6 alkoxy substituted C.sub.1-6 alkyl group (on the tetrazole ring, a phenyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1 substituted alkyl group. At least one group selected from the group consisting of 6 alkoxy groups may be substituted), a group selected from the group consisting of a phenyl C1-6 alkyl group and a C3-8 cycloalkyl C1-6 alkyl group Examples of the group which may be substituted include, for example, a [(5-tetrazolyl) methoxy] methyl group, a [2- (5-tetrazolyl) ethoxy] methyl group, a [3- (5-tetrazolyl) propoxy] methyl group, 2- (5-tetrazolyl) propoxy] methyl group, [4- (5-tetrazolyl) butoxy] methyl group, [5- (5-tetrazolyl) pe] Toxy] methyl group, [4- (1-tetrazolyl) pentoxy] methyl group, [6- (5- tetrazolyl) hexyloxy] methyl group, 2- [(1- tetrazolyl) methoxy] ethyl group, 1-[2- (5-tetrazolyl) ethoxy] ethyl group, 3- [3- (1-tetrazolyl) propoxy] propyl group, 4- [2- (5-tetrazolyl) propoxy] butyl group, 5- [4- (1-tetrazolyl) group Butoxy] hexyl group, 1,1-dimethyl-2- [5- (5-tetrazolyl) pentoxy] ethyl group, 2-methyl-3- [4- (1-tetrazolyl) pentoxy] propyl group, 2- [6- (5-tetrazolyl) hexyloxy! Ethyl group, {[1- (2-phenylethyl) -5-tetrazolyl] methoxy} methyl group, [(1-cyclohexylmethyl- -Tetrazolyl) methoxy] methyl group, [(5-benzyl-1-tetrazolyl) methoxy] methyl group, [(1-cyclopentylmethyl-5-tetrazolyl) methoxy] methyl group, {[5- (2-cyclohexylethyl)- 1-tetrazolyl] methoxy} methyl group, [(1-benzyl-5-tetrazolyl) methoxy] methyl group, [(1-cycloheptylmethyl-5-tetrazolyl) methoxy] methyl group, {[1- (3-phenylpropyl) group ) 5-tetrazolyl] methoxy} methyl group, [(1-phenyl-5-tetrazolyl) methoxy] methyl group, {[1- (4-trifluoromethoxyphenyl) -5-tetrazolyl] methoxy} methyl group, {[ 1- (4-trifluoromethylphenyl) -5-tetrazolyl] methoxy} methyl group, {[1- (4) Tetrazolyl C1-6 alkoxy substituted C1-6 alkyl group such as -chlorophenyl) -5-tetrazolyl] methoxy} methyl group (a phenyl group (a halogen atom, a halogen atom substituted or unsubstituted on a phenyl ring (a tetrazole ring on a tetrazole ring A group selected from the group consisting of a linear or branched alkyl group having 1 to 6 carbon atoms and a halogen-substituted or unsubstituted linear or branched alkoxy group having 1 to 6 carbon atoms is A group selected from the group consisting of 5, preferably 1 to 3 substituted, a phenyl C1-6 alkyl group and a C3-8 cycloalkyl C1-6 alkyl group may be substituted) Can be mentioned.

  Examples of the isoxazolyl C1-6 alkoxy-substituted C1-6 alkyl group (on the isoxazole ring, at least one C1-6 alkyl group may be substituted) include, for example, [(3-isoxazolyl) methoxy] methyl Group, [2- (4-isoxazolyl) ethoxy] methyl group, [3- (5-isoxazolyl) propoxy] methyl group, [2- (3-isoxazolyl) propoxy] methyl group, [4- (4-isoxazolyl) butoxy group Methyl group, [5- (5-isoxazolyl) pentoxy] methyl group, [4- (3- isoxazolyl) pentoxy] methyl group, [6- (4- isoxazolyl) hexyloxy] methyl group, 2- [(5- Isoxazolyl) methoxy] ethyl group, 1- [2- (3-isoxazolyl) ethoxy] ethyl Group, 3- [3- (4-isoxazolyl) propoxy] propyl group, 4- [2- (5-isoxazolyl) propoxy] butyl group, 5- [4- (3-isoxazolyl) butoxy] hexyl group, 1,1 -Dimethyl-2- [5- (4-isoxazolyl) pentoxy] ethyl group, 2-methyl-3- [4- (5-isoxazolyl) pentoxy] propyl group, 2- [6- (3-isoxazolyl) hexyloxy] Ethyl group, [(5-methyl-3-isoxazolyl) methoxy] methyl group, [(4-ethyl-3-isoxazolyl) methoxy] methyl group, [(3-n-propyl-4-isoxazolyl) methoxy] methyl group, [(5-n-Butyl-3-isoxazolyl) methoxy] methyl group, [(4-n-pentyl-3-isoxazolyl) Isoxazolyl C1-6 alkoxy substituted C1-6 alkyl such as [toxyl] methyl group, [(3-n-hexyl-5-isoxazolyl) methoxy] methyl group, [(4, 5-dimethyl-3- isoxazolyl) methoxy] methyl group A group (one or two C1-6 alkyl groups may be substituted on the isoxazole ring) can be mentioned.

  Benzothienyl C.sub.1-6 alkoxy substituted C.sub.1-6 alkyl group (on the benzothiophene ring, from the group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group As at least one selected group may be substituted), for example, [(3-benzothienyl) methoxy] methyl group, [2- (2-benzothienyl) ethoxy] methyl group, [3- (4-benzothienyl) propoxy] methyl group, [2- (5-benzothienyl) propoxy] methyl group, [4- (6-benzothienyl) butoxy] methyl group, [5- (7-benzothienyl) pentoxy] Methyl group, [4- (3-benzothienyl) pentoxy] methyl group, [6- (2-benzothienyl) hexyloxy] methyl group 2-[(4-benzothienyl) methoxy] ethyl group, 1- [2- (5-benzothienyl) ethoxy] ethyl group, 3- [3- (6-benzothienyl) propoxy] propyl group, 4- [2 -(7-benzothienyl) propoxy] butyl group, 5- [4- (3-benzothienyl) butoxy] hexyl group, 1,1-dimethyl-2- [5- (3-benzothienyl) pentoxy] ethyl group, 2-methyl-3- [4- (5-benzothienyl) pentoxy] propyl group, 2- [6- (3-benzothienyl) hexyloxy] ethyl group, [(5-methyl-3-benzothienyl) methoxy] Methyl group, [(4-ethyl-3-benzothienyl) methoxy] methyl group, [(5-chloro-3-benzothienyl) methoxy] methyl group, [(6-methyl-3-benzothienyl] Methoxy] methyl group, [(4-trifluoromethyl-3-benzothienyl) methoxy] methyl group, [(3-methoxy-5-benzothienyl) methoxy] methyl group, [(5-trifluoromethoxy-3-benzo] Thienyl) methoxy] methyl group, [(4,5-dichloro-3-benzothienyl) methoxy] methyl group, [(2,4,5-trifluoro-3-benzothienyl) methoxy] methyl group, [(4,4,5 Benzothienyl C1-6 alkoxy substituted C1 to 5 such as 5-dichloro-2-methyl-3-benzothienyl) methoxy] methyl group, [(4,5-dichloro-2-methoxy-3-benzothienyl) methoxy] methyl group, etc. 6 alkyl groups (on the benzothiophene ring, halogen atoms, halogen substituted or unsubstituted C.sub.1-6 alkyl groups and halogen substituted or halogenated One to three groups selected from the group consisting of unsubstituted C1-6 alkoxy groups may be substituted).

  1,3,4-oxadiazolyl C.sub.1-6 alkoxy substituted C.sub.1-6 alkyl group (1,3, 4-oxadiazole ring, phenyl group [phenyl ring, halogen atom, halogen substituted or unsubstituted As at least one of a group selected from the group consisting of a C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group may be substituted), for example, [(2-1,3,4-oxadiazolyl) methoxy] methyl group, [2- (2-1,3,4-oxadiazolyl) ethoxy] methyl group, [3- (2-1,3,4-oxadiazolyl) group Propoxy] methyl group, [2- (2-1,3,4-oxadiazolyl) propoxy] methyl group, [4- (2-1,3,4-oxadiazolyl) butoxy] methyl group, [5 (2-1,3,4-oxadiazolyl) pentoxy] methyl group, [4- (2-1,3,4-oxadiazolyl) pentoxy] methyl group, [6- (2-1,3,4-oxadiazolyl) hexyl Oxy] methyl group, 2-[(2-1,3,4-oxadiazolyl) methoxy] ethyl group, 1- [2- (2-1,3,4-oxadiazolyl) ethoxy] ethyl group, 3- [3- (2-1,3,4-oxadiazolyl) propoxy] propyl group, 4- [2- (2-1,3,4-oxadiazolyl) propoxy] butyl group, 5-[(2-1,3,4-oxadiazolyl] group ) Methoxy] pentyl group, 6- [4- (2-1,3,4-oxadiazolyl) butoxy] hexyl group, 1,1-dimethyl-2- [5- (2-1,3,4-oxadiazolyl) pentoxy ] Ethyl, 2-methyl-3- [4- (2-1,3,4-oxadiazolyl) pentoxy] propyl, 2- [6- (2-1,3,4-oxadiazolyl) hexyloxy] ethyl group, [5- (4-methylphenyl) -2-1,3,4-oxadiazolyl] methoxymethyl group, [5- (4-chlorophenyl) -2-1,3,4-oxadiazolyl] methoxymethyl group, [5- (4-Trifluoromethylphenyl) -2-1,3,4-oxadiazolyl] methoxymethyl group, [5- (4-methoxyphenyl) -2-1,3,4-oxadiazolyl] methoxymethyl group, [5- (4-Trifluoromethoxyphenyl) -2-1,3,4-oxadiazolyl] methoxymethyl group, [5- (2,4-dichlorophenyl) -2-1,3,4-oxadiazolyl [L] methoxymethyl group, [5- (2,4,6-trimethylphenyl) -2-1,3,4-oxadiazolyl] methoxymethyl group, [5- (2,4-dimethoxyphenyl) -2-1, A 1,3,4-oxadiazolyl C1-6 alkoxy-substituted C1-6 alkyl group such as a 3,4-oxadiazolyl] methoxymethyl group (on a 1,3,4-oxadiazole ring, a phenyl group [on a phenyl ring Is substituted by 1 to 5, preferably 1 to 3 groups selected from the group consisting of halogen atoms, halogen-substituted or unsubstituted C.sub.1-6 alkyl groups and halogen-substituted or unsubstituted C.sub.1-6 alkoxy groups; And the like may be substituted).

  As a C 2-6 alkynyloxy substituted C 1-6 alkyl group, for example, ethynyl oxymethyl group, 2-ethynyl oxymethyl group, 2- (2-ethynyl oxy) ethyl group, 1- (2-butynyloxy) ethyl group, 2 -(3-butynyloxy) ethyl group, 3- (1-methyl-2-propynyloxy) propyl group, 4- (2-pentynyloxy) butyl group, 4- (2-hexynyloxy) butyl group, 5- (2 -Propinyloxy) pentyl group, 6- (2-propynyloxy) hexyl group, 6- (2-butynyloxy) hexyl group, 1,1-dimethyl-2- (2-propynyloxy) ethyl group, 2-methyl-3 -(2-propynyloxy) propyl group etc. can be mentioned.

  As a naphthyl C1-6 alkoxy substituted C1-6 alkyl group, for example, (1-naphthyl) methoxymethyl group, [2- (2-naphthyl) ethoxy] methyl group, [3- (1-naphthyl) propoxy] methyl group , [2- (2-naphthyl) propoxy] methyl group, [4- (1-naphthyl) butoxy] methyl group, [5- (2-naphthyl) pentoxy] methyl group, [4- (1-naphthyl) pentoxy] Methyl group, [6- (1-naphthyl) hexyloxy] methyl group, 2-[(1-naphthyl) methoxy] ethyl group, 1- [2- (2-naphthyl) ethoxy] ethyl group, 3- [3- (1-Naphthyl) propoxy] propyl, 4- [2- (2-naphthyl) propoxy] butyl, 5- [4- (1-naphthyl) butoxy] pentyl, 6- [5- (2-naphthyl) Examples include pentoxy] hexyl group, 1,1-dimethyl-2- [4- (1-naphthyl) pentoxy] ethyl group, 2-methyl-3- [6- (1-naphthyl) hexyloxy] propyl group and the like. it can.

  As the 1,2,4-oxadiazolyl C1-6 alkoxy-substituted C1-6 alkyl group [a phenyl group may be substituted on the 1,2,4-oxadiazole ring], for example, [(3 -1,2,4-oxadiazolyl) methoxy] methyl group, [2- (5-1,2,4-oxadiazolyl) ethoxy] methyl group, [3- (3-1,2,4-oxadiazolyl) propoxy] methyl group Group, [2- (5-1,2,4-oxadiazolyl) propoxy] methyl group, [4- (3-1,2,4-oxadiazolyl) butoxy] methyl group, [5- (5-1,2,4, 4-oxadiazolyl) pentoxy] methyl group, [4- (3-1,2,4-oxadiazolyl) pentoxy] methyl group, [6- (3-1,2,4-oxadiazolyl) hexyloxy] methyl group, 2 [(5-1,2,4-oxadiazolyl) methoxy] ethyl group, 1- [2- (3-1,2,4-oxadiazolyl) ethoxy] ethyl group, 3- [3- (5-1,2,5 4-oxadiazolyl) propoxy] propyl group, 4- [2- (3-1,2,4-oxadiazolyl) propoxy] butyl group, 5-[(3-1,2,4-oxadiazolyl) methoxy] pentyl group, 6 -[4- (5-1,2,4-oxadiazolyl) butoxy] hexyl group, 1,1-dimethyl-2- [5- (3-1,2,4-oxadiazolyl) pentoxy] ethyl group, 2-methyl -3- [4- (5-1,2,4-oxadiazolyl) pentoxy] propyl group, 2- [6- (3-1,2,4-oxadiazolyl) hexyloxy] ethyl group, (5-phenyl-3 -1, 2, 4 1,2,4-Oxadiazolyl C1-6 alkoxy-substituted C1-6 alkyl group [1,2,4-, such as oxadiazolyl) methoxymethyl group, (3-phenyl-5-1,2,2,4-oxadiazolyl) methoxymethyl group, etc. On the oxadiazole ring, a phenyl group may be substituted] can be mentioned.

  A pyridyl C1-6 alkoxy substituted C1-6 alkyl group [wherein a pyridine ring is selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group; As at least one group of the above groups may be substituted], for example, (2-pyridyl) methoxymethyl group, [2- (3-pyridyl) ethoxy] methyl group, [3- (4-pyridyl) propoxy ] Methyl group, [2- (2- pyridyl) propoxy] methyl group, [4- (3- pyridyl) butoxy] methyl group, [5- (4- pyridyl) pentoxy] methyl group, [4- (2- pyridyl) ) Pentoxy] methyl group, [6- (3-pyridyl) hexyloxy] methyl group, 2-[(4-pyridyl) methoxy] ethyl group, 1- [2- (2- pyridin] ) Ethoxy] ethyl group, 3- [3- (3-pyridyl) propoxy] propyl group, 4- [2- (4-pyridyl) propoxy] butyl group, 5-[(2-pyridyl) methoxy] pentyl group, 6 -[4- (2-pyridyl) butoxy] hexyl group, 1,1-dimethyl-2- [5- (3-pyridyl) pentoxy] ethyl group, 2-methyl-3- [4- (4-pyridyl) pentoxy group A propyl group, 2- [6- (2-pyridyl) hexyloxy] ethyl group, (2-trifluoromethyl-5-pyridyl) methoxymethyl group, (4-chloro-2-pyridyl) methoxymethyl group, (3 -Trifluoromethyl-2-pyridyl) methoxymethyl group, (2-methoxy-4-pyridyl) methoxymethyl group, (2-trifluoromethoxy-5-pyridyl) methoxymethyl group, 2,4-dibromo-3-pyridyl) methoxymethyl group, (2,4,6-trimethyl-5-pyridyl) methoxymethyl group, (2,4-dimethoxy-5-pyridyl) methoxymethyl group, (2,4,6 Pyridyl C1-6 alkoxy-substituted C1-6 alkyl groups such as 6-trifluoro-3-pyridyl) methoxymethyl group [on a pyridine ring, halogen atoms, halogen-substituted or unsubstituted C1-6 alkyl groups and halogen-substituted or 1 to 3 groups selected from the group consisting of unsubstituted C1-6 alkoxy groups may be substituted.

  A thiazolyl C1-6 alkoxy substituted C1-6 alkyl group [wherein at least one phenyl group (a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen At least one group selected from the group consisting of substituted C1-6 alkoxy groups may be substituted) and at least one group selected from the group consisting of lower alkyl groups may be substituted ], For example, (4-thiazolyl) methoxymethyl group, [2- (2-thiazolyl) ethoxy] methyl group, [3- (5-thiazolyl) propoxy] methyl group, [2- (4-thiazolyl) propoxy group] A methyl group, a [4- (2-thiazolyl) butoxy] methyl group, a [5- (4-thiazolyl) pentoxy] methyl group, a [4- (5-thio) methyl group, Zoryl) pentoxy] methyl group, [6- (4-thiazolyl) hexyloxy] methyl group, 2-[(2-thiazolyl) methoxy] ethyl group, 1- [2- (5- thiazolyl) ethoxy] ethyl group, 3 -[3- (4-thiazolyl) propoxy] propyl group, 4- [2- (2-thiazolyl) propoxy] butyl group, 5-[(4-thiazolyl) methoxy] pentyl group, 6- [4- (5-) Thiazolyl) butoxy] hexyl group, 1,1-dimethyl-2- [5- (4-thiazolyl) pentoxy] ethyl group, 2-methyl-3- [4- (2-thiazolyl) pentoxy] propyl group, 2- [ 6- (5-thiazolyl) hexyloxy] ethyl group, [2- (4-methylphenyl) -4-thiazolyl] methoxymethyl group, [2- (4-chlorophenyl) -4-thiazolyl group Methoxymethyl group, [2- (4-trifluoromethylphenyl) -4-thiazolyl] methoxymethyl group, [5- (4-methoxyphenyl) -4-thiazolyl] methoxymethyl group, [2- (4-trifluoro) Methoxyphenyl) -4-thiazolyl] methoxymethyl group, [5- (2,4-dichlorophenyl) -2-thiazolyl] methoxymethyl group, [4- (2,4,6-trimethylphenyl) -2-thiazolyl] methoxy Methyl group, [4- (2,4-dimethoxyphenyl) -2-thiazolyl] methoxymethyl group, (2-methyl-4-thiazolyl) methoxymethyl group, (2,5-dimethyl-5-thiazolyl) methoxymethyl group And thiazolyl C1-6 alkoxy substituted C1-6 aryl such as (2-phenyl-4-methyl-5-thiazolyl) methoxymethyl group [1 to 2 phenyl groups (on the phenyl ring, halogen atoms, halogen-substituted or unsubstituted linear or branched alkyl groups having 1 to 6 carbon atoms, and halogen substitution Or 1 to 5, preferably 1 to 3 groups selected from the group consisting of unsubstituted C 1 to C 6 linear or branched alkoxy groups may be substituted and carbon number 1 1 to 2 groups selected from the group consisting of -6 linear or branched alkyl groups] may be mentioned.

  1,2,3,4-tetrahydronaphthyl C1-6 alkoxy substituted C1-6 alkyl group [in the 1,2,3,4-tetrahydronaphthalene ring, at least one C1-6 alkyl group is substituted, And the like] may be, for example, (6-1,2,3,4-tetrahydronaphthyl) methoxymethyl group, [2- (2-1,2,3,4-tetrahydronaphthyl) ethoxy] methyl group, [3 -(3-1,2,3,4-tetrahydronaphthyl) propoxy] methyl group, [2- (4-1,2,3,4-tetrahydronaphthyl) propoxy] methyl group, [4- (5-1,4) 2,3,4-tetrahydronaphthyl) butoxy] methyl group, [5- (6,1,2,3,4-tetrahydronaphthyl) pentoxy] methyl group, [4- (6,1,2,3,4-, Tetrahydronaphthyl Pentoxy] methyl group, [6- (5-1,2,3,4-tetrahydronaphthyl) hexyloxy] methyl group, 2-[(6-1,2,3,4-tetrahydronaphthyl) methoxy] ethyl group, 1- [2- (6,1,2,3,4-tetrahydronaphthyl) ethoxy] ethyl group, 3- [3- (5-1,2,3,4-tetrahydronaphthyl) propoxy] propyl group, 4- [2- (5-1,2,3,4-tetrahydronaphthyl) propoxy] butyl group, 5- [4- (6-1,2,3,4-tetrahydronaphthyl) butoxy] pentyl group, 6- [5 -(5-1,2,3,4-tetrahydronaphthyl) pentoxy] hexyl group, 1,1-dimethyl-2- [4- (6,1,2,3,4-tetrahydronaphthyl) pentoxy] ethyl group, 2-methyl-3- [6 (6-1,2,3,4-tetrahydronaphthyl) hexyloxy] propyl group, (1,1,4,4-tetramethyl-6-1,2,3,4-tetrahydronaphthyl) methoxymethyl group, 1,1,4-trimethyl-6-1,2,3,4-tetrahydronaphthyl) methoxymethyl group, (1,1-dimethyl-6-1,2,3,4-tetrahydronaphthyl) methoxymethyl group, 1,1-dimethyl-7-1,2,3,4-tetrahydronaphthyl) methoxymethyl group, (1-methyl-6-1,2,3,4-tetrahydronaphthyl) methoxymethyl group, Dimethyl-6-1,2,3,4-tetrahydronaphthyl) methoxymethyl group, (1,1,4,4-tetraethyl-6-1,2,3,4-tetrahydronaphthyl) methoxymethyl group, (1,1 1- Dimethyl-4-ethyl-6-1,2,3,4-tetrahydronaphthyl) methoxymethyl group, (1,1-di-n-propyl-6-1,2,3,4-tetrahydronaphthyl) methoxymethyl group Or (4,4-di-n-butyl-6-1,2,3,4-tetrahydronaphthyl) methoxymethyl group, (1-n-pentyl-6-1,2,3,4-tetrahydronaphthyl) methoxy Methyl group, (1,4-di-n-hexyl-6-1,2,3,4-tetrahydronaphthyl) methoxymethyl group, (1-methyl-5-n-propyl-4-ethyl-6-1, 1,2,3,4-tetrahydronaphthyl C1-6 alkoxy substituted C1-6 alkyl group [1,2,3,4-tetrahydronaphthalene ring such as 1,2,3,4-tetrahydronaphthyl) methoxymethyl group etc. 1 to 4 Serial C1~6 alkyl group can be exemplified] may be substituted.

  Carbamoyl C1-6 alkoxy substituted C1-6 alkyl group [C3-8 cycloalkyl group and phenyl group on the amino group (halogen atom, halogen substituted or unsubstituted C1-6 alkyl group and halogen on the phenyl ring At least one group selected from the group consisting of a group selected from the group consisting of a substituted or unsubstituted C1-6 alkoxy group may be substituted) Are, for example, carbamoylmethoxymethyl group, 2- (carbamoylethoxy) methyl group, (3-carbamoylpropoxy) methyl group, (2-carbamoylpropoxy) methyl group, (4-carbamoylbutoxy) methyl group, (5-carbamoyl) Pentoxy) methyl group, (4-carbamoyl pentoxy) methyl group, (6-carbamoyl Xyloxy) methyl group, 2- (carbamoyl methoxy) ethyl group, 1-(2- carbamoyl ethoxy) ethyl group, 3- (3- carbamoyl propoxy) propyl group, 4- (2- carbamoyl propoxy) butyl group, 5- ( Carbamoylmethoxy) pentyl group, 4- (2-carbamoylpropoxy) butyl group, 6- (4-carbamoylbutoxy) hexyl group, 1,1-dimethyl-2- (5-carbamoylpentoxy) ethyl group, 2-methyl- 3- (4-carbamoylpentoxy) propyl group, 2- (6-carbamoylhexyloxy) ethyl group, [N- (4-methylphenyl) carbamoyl] methoxymethyl group, [N- (4-chlorophenyl) carbamoyl] methoxy Methyl group, [N- (4-trifluoromethylphenyl) carbamoyl] Toxymethyl group, [N- (4-methoxyphenyl) carbamoyl] methoxymethyl group, [N- (4-trifluoromethoxyphenyl) carbamoyl] methoxymethyl group, [N- (2,4-dichlorophenyl) carbamoyl] methoxymethyl group , [N- (2,4,6-trimethylphenyl) carbamoyl] methoxymethyl group, [N- (2,4-dimethoxyphenyl) carbamoyl] methoxymethyl group, (N-cyclohexylcarbamoyl) methoxymethyl group, (N- Cyclopentylcarbamoyl) methoxymethyl group, (N-cycloheptylcarbamoyl) methoxymethyl group, (N-cyclooctylcarbamoyl) methoxymethyl group, (N-cyclobutylcarbamoyl) methoxymethyl group, (N-cyclopropylcarbamoyl) methoxymethyl group , (N-cyclopropyl-N-cyclohexylcarbamoyl) methoxymethyl group, (N, N-dicyclohexylcarbamoyl) methoxymethyl group, [N-cyclopropyl-N- (4-fluoromethylphenyl) carbamoyl] methoxymethyl group, A carbamoyl C1-6 alkoxy-substituted C1-6 alkyl group such as N-cyclohexyl-N- (4-fluoromethylphenyl) carbamoyl] methoxymethyl group (on an amino group, a C3-8 cycloalkyl group and a phenyl group [phenyl ring Above, 1 to 5 groups, preferably 1 to 3 groups selected from the group consisting of halogen atoms, halogen substituted or unsubstituted C1-6 alkyl groups and halogen substituted or unsubstituted C1-6 alkoxy groups One to two groups selected from the group consisting of May be) can be mentioned.

  Examples of the benzofuryl C1-6 alkoxy-substituted C1-6 alkyl group [at least one cyano group may be substituted on the benzofuran ring] include, for example, (2-benzofuryl) methoxymethyl group, 3-benzofuryl) ethoxy] methyl group, [3- (4-benzofuryl) propoxy] methyl group, [2- (5-benzofuryl) propoxy] methyl group, [4- (6-benzofuryl) butoxy] methyl group, [5 -(7-benzofuryl) pentoxy] methyl group, [4- (2-benzofuryl) pentoxy] methyl group, [6- (3-benzofuryl) hexyloxy] methyl group, 2-[(2-benzofuryl) methoxy] ethyl group 1- [2- (3-benzofuryl) ethoxy] ethyl group, 3- [3- (4-benzofuryl) propoxy] propyl group, 4 [2- (5-benzofuryl) propoxy] butyl group, 5- [4- (6-benzofuryl) butoxy] pentyl group, 6- [5- (7-benzofuryl) pentoxy] hexyl group, 1,1-dimethyl-2 -[4- (2-benzofuryl) pentoxy] ethyl group, 2-methyl-3- [6- (3-benzofuryl) hexyloxy] propyl group, (7-cyano-2-benzofuryl) methoxymethyl group, (6- Cyano-2-benzofuryl) methoxymethyl group, (5-cyano-2-benzofuryl) methoxymethyl group, (4-cyano-2-benzofuryl) methoxymethyl group, (3-cyano-2-benzofuryl) methoxymethyl group, 2-Cyano-5-benzofuryl) methoxymethyl group, (6,7-dicyano-2-benzofuryl) methoxymethyl group, (3,4,5- Rishiano 2- benzofuryl) [On benzofuran ring, may be substituted by one to three cyano groups] benzofuryl C1~6 alkoxy substituent C1~6 alkyl group such as a methoxymethyl group and the like.

  As the C 7-10 alkoxy group, for example, n-heptyloxy group, n-octyloxy group, n-nonyloxy group, n-decyloxy group, 5-methylhexyloxy group, 4, 4-dimethylpentyloxy group, 6- A methyl heptyloxy group, a 5, 5, 5- trimethyl pentyloxy group etc. can be mentioned.

  At least one kind of a group selected from the group consisting of phenyl C1-6 alkoxy group, C3-8 cycloalkyl group, C7-10 alkoxy group and phenoxy group is substituted on a phenoxy group [phenyl ring ], For example, 4-benzyloxyphenoxy group, 4-cyclohexylphenoxy group, 4-n-octyloxyphenoxy group, 4-cyclopentylphenoxy group, 3-phenoxyphenoxy group, 3-benzyloxyphenoxy group, 3-cyclohexyl Phenoxy group, 3-n-octyloxyphenoxy group, 3-cyclopentylphenoxy group, 4-phenoxyphenoxy group, 2-benzyloxyphenoxy group, 2-cyclohexylphenoxy group, 2-n-heptyloxyphenoxy group, 2-cyclopentylphenoxy Group, 2-fe 4-phenoxy-phenoxy, 4- (2-phenylethoxy) phenoxy, 4-cyclooctylphenoxy, 4-n-nonyloxyphenoxy, 4-cyclopropylphenoxy, 2,3-diphenoxyphenoxy, 4- ( 3-phenylpropoxy) phenoxy group, 4-cycloheptylphenoxy group, 4-n-decyloxyphenoxy group, 4-cyclobutylphenoxy group, 2,4,6-triphenoxyphenoxy group, 4- (4-phenylbutoxy) Phenoxy group, 2,4-dicyclohexylphenoxy group, 2,4-di-n-octyloxyphenoxy group, 2,4,6-tricyclopentylphenoxy group, 3-phenoxy-4-benzyloxyphenoxy group, 4- (5 -Phenylpentyloxy) phenoxy group, 4-cyclohexyl-3-fe Xyphenoxy group, 2,4,6-tri-n-octyloxyphenoxy group, 4-cyclopentyl-2-benzyloxyphenoxy group, 3-phenoxy-2-cyclohexylphenoxy group, 4- (6-phenylhexoxy) A phenoxy group such as a phenoxy group, a 3,4,5-tribenzyloxyphenoxy group, a 2,4-dibenzyloxyphenoxy group [in the phenyl ring, a phenyl C1-6 alkoxy group, a C3-8 cycloalkyl group, a C7 To 10 alkoxy groups and groups selected from the group consisting of phenoxy groups are substituted with 1 to 3 groups].

  As the 2,3-dihydrobenzofuryloxy group [at least one oxo group may be substituted on the 2,3-dihydrobenzofuran ring], for example, (2-, 3-, 4-, 5-, 6- or 7-) 2,3-dihydrobenzofuryloxy group, 3-oxo-6-2,3-dihydrobenzofuryloxy group, 2-oxo-5-2,3-dihydrobenzofuryloxy group And the like, [one or two oxo groups may be substituted on the 2,3-dihydrobenzofuran ring] can be mentioned.

  Examples of the benzothiazolyloxy group [at least one C1-6 alkyl group may be substituted on the benzothiazole ring] include, for example (2-, 4-, 5-, 6- or 7- -) Benzothiazolyloxy group, 2-methyl-5-benzothiazolyloxy group, 2-ethyl-5-benzothiazolyloxy group, 2-n-propyl-5-benzothiazolyloxy group, 2-tert-butyl-5-benzothiazolyloxy group, 2-n-pentyl-5-benzothiazolyloxy group, 2-n-hexyl-5-benzothiazolyloxy group, 2,5-dimethyl A benzothiazolyloxy group such as a 6-benzothiazolyloxy group, a 4,5,6-trimethyl-2-benzothiazolyloxy group, etc. [1 to 3 C1-6 alkyls on a benzothiazole ring Even if the group is substituted ] Can be mentioned.

  Examples of the furyl C1-6 alkoxy group [at least one C1-6 alkoxycarbonyl group may be substituted on the furan ring] include, for example, (2- or 3-) furylmethoxy group, 2- [2 (2- or 3-) furyl] ethoxy group, 1-[(2- or 3-) furyl] ethoxy group, 3-[(2- or 3-) furyl] propoxy group, 2-[(2- or 3) -) Furyl] propoxy group, 4-[(2- or 3-) furyl] butoxy group, 5-[(2- or 3-) furyl] pentoxy group, 4-[(2- or 3-) furyl] pentoxy Group, 6-[(2- or 3-) furyl] hexyloxy group, 2-methyl-3-[(2- or 3-) furyl] propoxy group, 1,1-dimethyl-2-[(2- or 3-) Furyl] ethoxy group, 2-ethoxycarbonyl-5-furylme Xy group, 2-ethoxycarbonyl-5-furylmethoxy group, 2-methoxycarbonyl-4-furylmethoxy group, 2-propoxycarbonyl-3-furylmethoxy group, 2-butoxycarbonyl-5-furylmethoxy group, 2-pentyl Oxycarbonyl-5-furylmethoxy, 2-hexyloxycarbonyl-5-furylmethoxy, 2,3-diethoxycarbonyl-5-furylmethoxy, 2,3,4-trimethoxycarbonyl-5-furylmethoxy And the like, [wherein, on the furan ring, 1 to 3 C1-6 alkoxycarbonyl groups may be substituted] can be mentioned.

  As a tetrazolyl C1-6 alkoxy group [in the tetrazole ring, at least one of a group selected from the group consisting of a phenyl C1-6 alkyl group and a C3-8 cycloalkyl C1-6 alkyl group may be substituted] Are, for example, (1-, 2- or 5-) tetrazolylmethoxy, 2-[(1-, 2- or 5-) tetrazolyl] ethoxy, 1-[(1-, 2- or 5-) ) Tetrazolyl] ethoxy group, 3-[(1-, 2- or 5-) tetrazolyl] propoxy group, 2-[((1-, 2- or 5-) tetrazolyl) propoxy group, 4-[(1-, 2- or 5-) tetrazolyl] butoxy group, 5-[(1-, 2- or 5-) tetrazolyl] pentoxy group, 4-[(1-, 2- or 5-) tetrazolyl] pentoxy group, 6- [6 (1-, 2- or 5-) Razolyl] hexyloxy group, 2-methyl-3-[(1-, 2- or 5-) tetrazolyl] propoxy group, 1,1-dimethyl-2-[(1-, 2- or 5-) tetrazolyl] ethoxy Group, 1- (2-phenylethyl) -5-tetrazolylmethoxy group, 1-cyclohexylmethyl-5-tetrazolylmethoxy group, 5-benzyl-1-tetrazolylmethoxy group, 5- (2-cyclopentyl) Ethyl) -1-tetrazolylmethoxy, 1-benzyl-5-tetrazolylmethoxy, 1- (3-phenylpropyl) -5-tetrazolylmethoxy, 1- (4-phenylbutyl) -5 -Tetrazolylmethoxy group, 1- (5-phenylpentyl) -5-tetrazolylmethoxy group, 1- (6-phenylhexyl) -5-tetrazolylmethoxy group, 1-cyclo Tylmethyl-5-tetrazolylmethoxy, 1- (3-cyclopropylpropyl) -5-tetrazolylmethoxy, 1- (4-cycloheptylbutyl) -5-tetrazolylmethoxy, 1- (5 Tetrazolyl C.sub.1-6 alkoxy group such as 4-cyclooctyllpentyl) -5-tetrazolylmethoxy group, 1- (6-cyclohexylhexyl) -5-tetrazolylmethoxy group, etc. And the group selected from the group consisting of an alkyl group and a C3-8 cycloalkyl C1-6 alkyl group may be substituted with one.

  1,2,4-oxadiazolyl C1-6 alkoxy group [1,2,4 oxadiazole ring on the phenyl group (phenyl ring on the halogen atom, halogen substituted or unsubstituted C1-6 alkyl group And at least one of a group selected from the group consisting of halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted], for example, (3- or 5 -) 1,2,4-oxadiazolylmethoxy group, 2-[(3- or 5-) 1,2,4-oxadiazolyl] ethoxy group, 1-[(3- or 5-) 1,2,4 -Oxadiazolyl] ethoxy group, 3-[(3- or 5-) 1,2,4-oxadiazolyl] propoxy group, 2-[(3- or 5-) 1,2,4-oxadiazolyl] propoxy group, 4- [(3 or -) 1,2,4-oxadiazolyl] butoxy group, 5-[(3- or 5-) 1,2,4-oxadiazolyl] pentoxy group, 4-[(3- or 5-) 1,2,4- Oxadiazolyl] pentoxy group, 6-[(3- or 5-) 1,2,4-oxadiazolyl] hexyloxy group, 2-methyl-3-[(3- or 5-) 1,2,4-oxadiazolyl] propoxy Group, 1,1-dimethyl-2-[(3- or 5-) 1,2,4-oxadiazolyl] ethoxy group, 3- (4-tert-butylphenyl) -5-1,2,4-oxadiazo Group, 3-phenyl-5-1,2-, 4-oxadiazolylmethoxy group, 3- (4-chlorophenyl) -5-1,2,4-oxadiazolylmethoxy group, 3- (4-trichloro) Fluoromethylphenyl) -5- , 2,4-oxadiazolylmethoxy, 5- (4-trifluoromethoxyphenyl) -3-1,2,4-oxadiazolylmethoxy, 5- (4-methoxyphenyl) -3-1,2 , 4-Oxadiazolyl methoxy group, 5- (2, 4- dimethylphenyl) -3- 1, 2, 4- oxadiazolyl methoxy group, 3- (2, 4, 6- trimethylphenyl) -5-1 , 2,4-oxadiazolylmethoxy, 3- (2,4-dimethylphenyl) -5-1,2,4-oxadiazolylmethoxy, 5- (2,4,6-trimethoxyphenyl)- 3-1,2,4-oxadiazolylmethoxy, 3- (2,4-dibromophenyl) -5-1,2,4-oxadiazolylmethoxy, 3- (2,4,6-trifluoro Phenyl) -5-1,2,4-oxa Diazolylmethoxy, 3- (3,5-dichlorophenyl) -5-1,2,4-oxadiazolylmethoxy, 3- (2-methyl-5-chlorophenyl) -5-1,2,4-oxa Diazolylmethoxy group, 3- (3-methoxy-5-chlorophenyl) -5-1,2,4-oxadiazolylmethoxy group, 3- (2,3,4,5,6-pentafluorophenyl) -5 1,2,4-oxadiazolyl C.sub.1-6 alkoxy group such as a 1,2,4-oxadiazolylmethoxy group [a phenyl group (a phenyl ring on a 1,2,4-oxadiazole ring, 1 to 5, preferably 1 to 3 groups selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group are substituted The Good) can be mentioned] may be substituted.

  Examples of the benzothienyl C1-6 alkoxy group [at least one halogen atom may be substituted on the benzothiophene ring] include, for example (2-, 3-, 4-, 5-, 6- or 7-) benzothienyl methoxy group, 2-[(2-, 3-, 4-, 5-, 6- or 7-) benzothienyl] ethoxy group, 1-[(2-, 3-, 4-, 5 -, 6 or 7-) benzothienyl] ethoxy group, 3-[(2-, 3-, 4-, 5-, 6- or 7-) benzothienyl] propoxy group, 2-[(2-, 3) -, 4-, 5-, 6- or 7-) benzothienyl] propoxy group, 4-[(2-, 3-, 4-, 5-, 6- or 7-) benzothienyl] butoxy group, 5- [(2-, 3-, 4-, 5-, 6- or 7-) benzothienyl] pentoxy group, 4-[(2-, 3-,- -, 5-, 6- or 7-) benzothienyl] pentoxy group, 6-[(2-, 3-, 4-, 5-, 6- or 7-) benzothienyl] hexyloxy group, 2-methyl- 3-[(2-, 3-, 4-, 5-, 6- or 7-) benzothienyl] propoxy group, 1,1-dimethyl-2-[(2-, 3-, 4-, 5-, 5-, 6- or 7-) benzothienyl] ethoxy group, 5-chloro-3-benzothienylmethoxy group, 4-bromo-2-benzothienylmethoxy group, 6-fluoro-5-benzothienylmethoxy group, 7-iodo-4 Benzothienyl C1-6 alkoxy groups such as -1,2,4-oxadiazolylmethoxy, 4,5-dichloro-3-benzothienylmethoxy, 3,4,5-trifluoro-2-benzothienylmethoxy and the like [On the benzothiophene ring 1 to 3 halogen atoms can be mentioned] may be substituted.

  Examples of the isoxazolyl C1-6 alkoxy group [at least one C1-6 alkyl group may be substituted on the isoxazole ring] include, for example, (3-, 4- or 5-) isoxazolyl Methoxy group, 2-[(3-, 4- or 5-) isoxazolyl] ethoxy group, 1-[(3-, 4- or 5-) isoxazolyl] ethoxy group, 3-[(3-, 4- or 5] -) Isoxazolyl] propoxy group, 2-[(3-, 4- or 5-) isoxazolyl] propoxy group, 4-[(3-, 4- or 5-) isoxazolyl] butoxy group, 5-[(3-, 4- or 5-) isoxazolyl] pentoxy group, 4-[(3-, 4- or 5-) isoxazolyl] pentoxy group, 6-[(3-, 4- or 5-) isoxazolyl] hexyloxy group, -Methyl-3-[(3-, 4- or 5-) isoxazolyl] propoxy group, 1,1-dimethyl-2-[(3-, 4- or 5-) isoxazolyl] ethoxy group, (3,5- Dimethyl-4-isoxazolyl) methoxy, (3-methyl-5-isoxazolyl) methoxy, (4-ethyl-5-isoxazolyl) methoxy, (5-n-propyl-4-isoxazolyl) methoxy, (3- Isoxazolyl C1-6 alkoxy group [isoxazole ring such as tert-butyl-4-isoxazolyl) methoxy group, (4-n-pentyl-5-isoxazolyl) methoxy group, (5-n-hexyl-5-isoxazolyl) methoxy group, etc. Above, one to two C1-6 alkyl groups may be substituted].

  1,3,4-oxadiazolyl C1-6 alkoxy [1, 3,4-oxadiazole ring on which at least one phenyl group (on the phenyl ring at least one C1-6 alkyl group is attached And the like] may be substituted], for example, a 2-1,3,4-oxadiazolylmethoxy group, a 2- (2-1,3,4-oxadiazolyl) ethoxy group, 1- (2-1,3,4-oxadiazolyl) ethoxy group, 3- (2-1,3,4-oxadiazolyl) propoxy group, 2- (2-1,3,4-oxadiazolyl) propoxy group, 4- (2-1,3,4-oxadiazolyl) butoxy group, 5- (2-1,3,4-oxadiazolyl) pentoxy group, 4- (2-1,3,4-oxadiazolyl) pentoxy group, 6- (2 -1, 3, 4 Oxadiazolyl) hexyloxy group, 2-methyl-3- (2-1,3,4-oxadiazolyl) propoxy group, 1,1-dimethyl-2- (2-1,3,4-oxadiazolyl) ethoxy group, 2- (4-Methylphenyl) -5-1,3,4-oxadiazolylmethoxy, 3-phenyl-5-1,3,4-oxadiazolylmethoxy, 2- (4-ethylphenyl) -5- 1,3,4-oxadiazolylmethoxy, 3- (4-n-propylphenyl) -5-1,3,4-oxadiazolylmethoxy, 3- (4-sec-butylphenyl) -5- 1,3,4-oxadiazolylmethoxy, 3- (4-n-pentylphenyl) -5-1,3,4-oxadiazolylmethoxy, 3- (2,4-dimethylphenyl) -5- 1, 3, 4-Oki Diazolylmethoxy group, 3- (2,4,6-trimethylphenyl) -5-1,3,4-oxadiazolylmethoxy group, 3- (3-n-hexylphenyl) -5-1,3,4 -Oxadiazolylmethoxy, 3- (2-methylphenyl) -5-1,3,4-oxadiazolylmethoxy, 3- (3-methylphenyl) -5-1,2,4-oxadiazolyl 1,3, 4-oxadiazolyl C1-6 alkoxy group such as methoxy group [1,3,4-oxadiazole ring, one phenyl group (one to three C1 6 alkyl group may be substituted) may be mentioned.

  As the naphthyl C1-6 alkoxy group, for example, (2- or 3-) naphthylmethoxy group, 2-[(2- or 3-) naphthyl] ethoxy group, 1-[(2- or 3-) naphthyl] ethoxy Group, 3-[(2- or 3-) naphthyl] propoxy group, 2-[(2- or 3-) naphthyl] propoxy group, 4- (2- or 3-) naphthyl] butoxy group, 5-[( 2- or 3-) naphthyl] pentoxy group, 4- (1- or 2-) naphthyl] pentoxy group, 6- (2- or 3-) naphthyl] hexyloxy group, 2-methyl-3-[(2- Or 3-) naphthyl] propoxy group, 1,1-dimethyl-2-[(2- or 3-) naphthyl] ethoxy group and the like.

  Examples of the pyridyl C1-6 alkoxy group (in which at least one halogen-substituted or unsubstituted C1-6 alkyl group may be substituted on the pyridine ring) include, for example, (1-, 2-, 3- Or 4-) pyridylmethoxy, 2-[(1-, 2-, 3- or 4-) pyridyl] ethoxy, 1-[(1-, 2-, 3- or 4-) pyridyl] ethoxy, 3-[(1-, 2-, 3- or 4-) pyridyl] propoxy group, 2-[(1-, 2-, 3- or 4-) pyridyl] propoxy group, 4-[(1-, 2) -, 3- or 4-) pyridyl] butoxy group, 5- [1-, 2-, 3- or 4-] pyridyl] pentoxy group, 4-[(1-, 2-, 3- or 4-) pyridyl ] Pentoxy group, 6-[(1-, 2-, 3- or 4-) pyridyl] hexyloxy group, 2-methy -3-[(1-, 2-, 3- or 4-) pyridyl] propoxy group, 1, 1-dimethyl-2-[(1-, 2-, 3- or 4-) pyridyl] ethoxy group, 2 -Trifluoromethyl-5-pyridylmethoxy group, 2-methyl-5-pyridylmethoxy group, 2-ethyl-6-pyridylmethoxy group, 3-n-propyl-2-pyridylmethoxy group, 4-n-butyl-5 group -Pyridylmethoxy, 3-n-pentyl-4-pyridylmethoxy, 2-n-hexyl-6-pyridylmethoxy, 2,3-ditrifluoromethyl-5-pyridylmethoxy, 3,4,5-triyl Pyridyl C1-6 alkoxy groups such as fluoromethyl-2-pyridylmethoxy, 2,4-dimethyl-5-pyridylmethoxy, 3,4,5-trimethyl-2-pyridylmethoxy and the like (on a pyridine ring May 1-3 C1~6 alkyl groups halogen-substituted or unsubstituted of substituted) can be exemplified.

  A thiazolyl C1-6 alkoxy group [in which at least one phenyl group (a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or Examples of the group (2) in which at least one group selected from the group consisting of an alkoxy group may be substituted may be substituted with, for example, a (2-, 4- or 5-) thiazolyl methoxy group , 2-[(2-, 4- or 5-) thiazolyl] ethoxy group, 1-[(2-, 4- or 5-) thiazolyl] ethoxy group, 3-[(2-, 4- or 5-) group Thiazolyl] propoxy group, 2-[(2-, 4- or 5-) thiazolyl] propoxy group, 4-[(2-, 4- or 5-) thiazolyl] butoxy group, 5-[(2-, 4-) Or 5-) thiazolyl] pent And 4-[(2-, 4- or 5-) thiazolyl] pentoxy group, 6-[(2-, 4- or 5-) thiazolyl] hexyloxy group, 2-methyl-3-[(2- , 4- or 5-) thiazolyl] propoxy group, 1,1-dimethyl-2-[(2-, 4- or 5-) thiazolyl] ethoxy group, 2- (4-trifluoromethylphenyl) -4-thia Zorylmethoxy, 2-phenyl-4-thiazolylmethoxy, 2- (4-chlorophenyl) -4-thiazolylmethoxy, 2- (4-trifluoromethylphenyl) -5-thiazolylmethoxy Group, 2- (4-trifluoromethoxyphenyl) -4-thiazolylmethoxy group, 5- (4-methoxyphenyl) -3-thiazolylmethoxy group, 5- (2,4-dimethylphenyl) -2 -Thiazolyl methoxy group, -(2,4,6-trimethylphenyl) -2-thiazolylmethoxy, 2- (2,4-dimethylphenyl) -5-thiazolylmethoxy, 2- (2,4,6-trimethoxy) Phenyl) -4-thiazolylmethoxy, 2- (2,4-dibromophenyl) -4-thiazolylmethoxy, 2- (2,4,6-trifluorophenyl) -5-thiazolylmethoxy , 2- (3,5-dichlorophenyl) -4-thiazolylmethoxy, 2- (2-methyl-5-chlorophenyl) -4-thiazolylmethoxy, 2- (3-methoxy-5-chlorophenyl) ) 4-thiazolyl methoxy group, 2- (2,3,4,5,6-pentafluorophenyl) -4-thiazolyl methoxy group, 2,5-diphenyl-4-thiazolyl methoxy group etc. Thiazolyl C1-6 alkoxy [1 to 2 phenyl groups (on the phenyl ring, halogen atoms, halogen substituted or unsubstituted C.sub.1-6 alkyl groups and halogen substituted or unsubstituted C.sub.1-6 alkoxy groups. Group (s) selected from the group consisting of 1 to 5 and preferably 1 to 3 may be substituted].

  As a 1,2,3,4-tetrahydronaphthyl C1-6 alkoxy group (at least one C1-6 alkyl group may be substituted on the 1,2,3,4-tetrahydronaphthalene ring). For example, (1-, 2-, 5- or 6-) 1, 2, 3, 4-tetrahydronaphthylmethoxy group, 2-[(1-, 2-, 5- or 6-) 1, 2, 3 4, 4- tetrahydronaphthyl] ethoxy group, 1-[(1-, 2, 5- or 6-) 1, 2, 3, 4-tetrahydronaphthyl] ethoxy group, 3-[(1-, 2, 5) -Or 6-) 1,2,3,4-tetrahydronaphthyl] propoxy group, 2-[(1-, 2, 5- or 6-) 1,2,3,4-tetrahydronaphthyl] propoxy group, 4 -[(1- or 2-) 1,2,3,4-tetrahydronaphthyl] butoxy group, -[(1- or 2-) 1,2,3,4-tetrahydronaphthyl] pentoxy group, 4-[(1-, 2, 5- or 6-) 1,2,3,4-tetrahydronaphthyl] Pentoxy group, 6-[(1-, 2, 5- or 6-) 1, 2, 3, 4-tetrahydronaphthyl] hexyloxy group, 2-methyl-3-[(1-, 2, 5-) Or 6-) 1,2,3,4-tetrahydronaphthyl] propoxy group, 1,1-dimethyl-2-[(1-, 2, 5- or 6-) 1,2,3,4-tetrahydronaphthyl ] Ethoxy group, (1,1,4,4-tetramethyl-6-1,2,3,4-tetrahydronaphthyl) methoxy group, (1,1,4-trimethyl-6-1,2,3,4 -Tetrahydronaphthyl) methoxy, (1,1-dimethyl-6-1,2,3,4-tetrahydric) Naphthyl) methoxy group, (4,4-dimethyl-6-1,2,3,4-tetrahydronaphthyl) methoxy group, (1-methyl-6-1,2,3,4-tetrahydronaphthyl) methoxy group, ( 1,4-dimethyl-6-1,2,3,4-tetrahydronaphthyl) methoxy group, (1,1,4,4-tetraethyl-6-1,2,3,4-tetrahydronaphthyl) methoxy group, 1,1-Dimethyl-4-ethyl-6-1,2,3,4-tetrahydronaphthyl) methoxy group, (1,1-di n-propyl-6-1,2,3,4-tetrahydronaphthyl) methoxy Group, (4,4-di-n-butyl-6-1,2,3,4-tetrahydronaphthyl) methoxy group, (1-n-pentyl-6-1,2,3,4-tetrahydronaphthyl) methoxy group Group, (1,4-di n-hex 6-1, 2, 3, 4-tetrahydronaphthyl) methoxy group, (1-methyl-5-n-propyl 4-ethyl 6- 1, 2, 3, 4-tetrahydronaphthyl) methoxy group, etc. 1 And 2,3,4 tetrahydronaphthyl C1-6 alkoxy groups (1 to 4 C1-6 alkyl groups may be substituted on the 1,2,3,4-tetrahydronaphthalene ring) be able to.

  A phenoxy C.sub.1-6 alkoxy group (on the phenyl ring, at least one of a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group; As the species may be substituted), for example, phenoxymethoxy group, 2-phenoxyethoxy group, 1-phenoxyethoxy group, 3-phenoxypropoxy group, 2-phenoxypropoxy group, 4-phenoxybutoxy group, 5- Phenoxypentoxy group, 4-phenoxypentoxy group, 6-phenoxyhexyloxy group, 2-methyl-3-phenoxypropoxy group, 1,1-dimethyl-2-phenoxyethoxy group, 2-fluorophenoxymethoxy group, 3- Fluorophenoxy methoxy group, 4-fluorophenoxy methoxy Group, 2- (2-fluorophenoxy) ethoxy group, 2- (3-fluorophenoxy) ethoxy group, 2- (4-fluorophenoxy) ethoxy group, 2-chlorophenoxymethoxy group, 3-chlorophenoxymethoxy group, 4 3-chlorophenoxymethoxy, 2-fluoro-4-bromophenoxymethoxy, 4-chloro-3-fluorophenoxymethoxy, 2-chloro-4-fluorophenoxymethoxy, 3,4-dichlorophenoxymethoxy, 3, 5-dichlorophenoxymethoxy group, 2,3-dichlorophenoxymethoxy group, 2,5-dichlorophenoxymethoxy group, 2,3,4-trichlorophenoxymethoxy group, 3,4,5-trifluorophenoxymethoxy group, 2, 3,4,5,6-pentafluorophenoxy methoxy group, 2 4,6-Trichlorophenoxymethoxy, 4-isopropylphenoxymethoxy, 4-n-butylphenoxymethoxy, 4-methylphenoxymethoxy, 2-methylphenoxymethoxy, 3-methylphenoxymethoxy, 2,4- Dimethyl phenoxy methoxy group, 2,3-dimethyl phenoxy methoxy group, 2, 6- dimethyl phenoxy methoxy group, 3,5- dimethyl phenoxy methoxy group, 2, 5- dimethyl phenoxy methoxy group, 2, 4, 6- trimethyl phenoxy methoxy Group, 4-ethylphenoxymethoxy group, 4-isopropylphenoxymethoxy group, 3,5-ditrifluoromethylphenoxymethoxy group, 4-isopropoxyphenoxymethoxy group, 4-n-butoxyphenoxymethoxy group, 4-methoxyphenoxy group Toxy, 2-methoxyphenoxymethoxy, 3-methoxyphenoxymethoxy, 2,4-dimethoxyphenoxymethoxy, 2,3-dimethoxyphenoxymethoxy, 2,6-dimethoxyphenoxymethoxy, 3,5-dimethoxyphenoxy Methoxy group, 2,5-dimethoxyphenoxymethoxy group, 2,4,6-trimethoxyphenoxymethoxy group, 3,5-ditrifluoromethoxyphenoxymethoxy group, 2-isopropoxyphenoxymethoxy group, 3-chloro-4-methoxy Phenoxymethoxy group, 2-chloro-4-trifluoromethoxyphenoxymethoxy group, 3-methyl-4-fluorophenoxymethoxy group, 4-bromo-3-trifluoromethylphenoxymethoxy group, 2- (2-chlorophenoxy) ethoxy Group 2- 3-chlorophenoxy) ethoxy group, 2- (4-chlorophenoxy) ethoxy group, 2-trifluoromethylphenoxymethoxy group, 3-trifluoromethylphenoxymethoxy group, 4-trifluoromethylphenoxymethoxy group, 2-trifluoro Methoxy phenoxy methoxy group, 3-trifluoro methoxy phenoxy methoxy group, 4- trifluoro methoxy phenoxy methoxy group, 2- (2- trifluoromethyl phenoxy) ethoxy group, 2- (3- trifluoromethyl phenoxy) ethoxy group, 2 — (4-trifluoromethylphenoxy) ethoxy group, 2- (2-trifluoromethoxyphenoxy) ethoxy group, 2- (3-trifluoromethoxyphenoxy) ethoxy group, 2- (4-trifluoromethoxyphenoxy) ethoxy group , 3 (2-trifluoromethylphenoxy) propoxy group, 3- (3-trifluoromethylphenoxy) propoxy group, 3- (4-trifluoromethylphenoxy) propoxy group, 3- (2-trifluoromethylphenoxy) propoxy group, 3- (3-trifluoromethoxyphenoxy) propoxy group, 3- (4-trifluoromethoxyphenoxy) propoxy group, 4- (3-trifluoromethylphenoxy) butoxy group, 5- (4-trifluoromethylphenoxy) pentoxy group Group, 4- (4-trifluoromethylphenoxy) pentoxy group, 4- (4-trifluoromethoxyphenoxy) pentoxy group, 6- (3-trifluoromethylphenoxy) hexyloxy group, 6- (4-trifluoromethyl) Phenoxy) hexyloxy group, 6- (4-) From a phenoxy C1-6 alkoxy group such as a trifluoromethoxyphenoxy) hexyloxy group (on the phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group 1 to 5, preferably 1 to 3 groups selected from the group consisting of

  A carbamoyl C1-6 alkoxy group [on an amino group a C3-8 cycloalkyl group and a phenyl group (on a phenyl ring a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted At least one group selected from the group consisting of a group selected from the group consisting of a C1-6 alkoxy group) may be substituted], for example, Carbamoyl methoxy group, 2-carbamoyl ethoxy group, 3-carbamoyl propoxy group, 2-carbamoyl propoxy group, 4-carbamoyl butoxy group, 5-carbamoyl pentoxy group, 4-carbamoyl pentoxy group, 6-carbamoylhexyloxy group, 2 -Methyl-3-carbamoylpropoxy group, 1,1-dimethyl-2-carbamoyl ester Xy group, [N- (4-methylphenyl) carbamoyl] methoxy group, [N- (4-chlorophenyl) carbamoyl] methoxy group, [N- (4-trifluoromethylphenyl) carbamoyl] methoxy group, [N- ( 4-methoxyphenyl) carbamoyl] methoxy group, [N- (4-trifluoromethoxyphenyl) carbamoyl] methoxy group, [N- (2,4-dichlorophenyl) carbamoyl] methoxy group, [N- (2,4,6 -Trimethylphenyl) carbamoyl] methoxy, [N- (2,4-dimethoxyphenyl) carbamoyl] methoxy, (N-cyclohexylcarbamoyl) methoxy, (N-cyclopentylcarbamoyl) methoxy, (N-cycloheptylcarbamoyl) Methoxy group, (N-cyclooctylcarbamoyl Methoxy group, (N-cyclobutylcarbamoyl) methoxy group, (N-cyclopropylcarbamoyl) methoxy group, (N-cyclopropyl-N-cyclohexylcarbamoyl) methoxy group, (N, N-dicyclohexylcarbamoyl) methoxy group, [N Carbamoyl C1-6 alkoxy groups such as -cyclopropyl-N- (4-fluoromethylphenyl) carbamoyl] methoxy group, [N-cyclohexyl-N- (4-fluoromethylphenyl) carbamoyl] methoxy group, etc. [on the amino group A C 3-8 cycloalkyl group and a phenyl group (on the phenyl ring, selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group 1 to 5 groups, preferably 1 to 3 groups, Or two or more groups selected from the group consisting of

  Examples of the benzofuryl C1-6 alkoxy group (wherein at least one cyano group may be substituted on the benzofuran ring) include, for example, (2-benzofuryl) methoxy group, 2- (3-benzofuryl) ethoxy group, 3- (4-benzofuryl) propoxy group, 2- (5-benzofuryl) propoxy group, 4- (6-benzofuryl) butoxy group, 5- (7-benzofuryl) pentoxy group, 4- (2-benzofuryl) pentoxy group, 6- (3-benzofuryl) hexyloxy group, 2- (2-benzofuryl) methoxy group, 1,1-dimethyl-2- (2-benzofuryl) ethoxy group, 2-methyl-3- (3-benzofuryl) propoxy group , (7-cyano-2-benzofuryl) methoxy group, (6-cyano-2-benzofuryl) methoxy group, (5-cyano-2-beta) group Zofuryl) methoxy group, (4-cyano-2-benzofuryl) methoxy group, (3-cyano-2-benzofuryl) methoxy group, (2-cyano-5-benzofuryl) methoxy group, (6, 7-dicyano-2-yl) Benzofuryl C1-6 alkyl group such as benzofuryl) methoxy group, (3,4,5-tricyano-2-benzofuryl) methoxy group (1 to 3 cyano groups may be substituted on the benzofuran ring) Can be mentioned.

  As the naphthyloxy C1-6 alkyl group (on the naphthalene ring, at least one C1-6 alkoxy group may be substituted), for example, a (1- or 2-) naphthyloxymethyl group, 2- [(1- or 2-) naphthyloxy] ethyl group, 1-[(1- or 2-) naphthyloxy] ethyl group, 3-[(1- or 2-) naphthyloxy] propyl group, 2-[( 1- or 2-) naphthyloxy] butyl group, 5-[(1- or 2-) naphthyloxy] pentyl group, 4-[(1- or 2-) naphthyloxy] pentyl group, 6-[(1- Or 2-) naphthyloxy] hexyl group, 2-methyl-3-[(1- or 2-) naphthyloxy] propyl group, 1,1-dimethyl-2-[(1- or 2-) naphthyloxy] ethyl Group, 2- (4-methoxy-1-) Phenyloxy) ethyl group, (4-methoxy-1-naphthyloxy) methyl group, 2- (3-ethoxy-1-naphthyloxy) ethyl group, 2-n-propoxy-1-naphthyloxymethyl group, 5-tert- Butoxy-2-naphthyloxymethyl group, 6-n-pentyloxy-3-naphthyloxymethyl group, 7-n-hexyloxy-4-naphthyloxymethyl group, 2- (2,4-dimethoxy-1-naphthyoloxy) group Naphthyloxy C1-6 alkyl groups such as ethyl group, 2- (1,2,3,4-tetramethoxy-5-naphthyoloxy) ethyl group, etc. (1-4 C1-6 alkoxy groups are present on the naphthalene ring And the like) can be mentioned.

  Examples of the benzothiazolyloxy C1-6 alkyl group (in which at least one C1-6 alkyl group may be substituted on the benzothiazole ring) include, for example (2-, 4-, 5-, 6- or 7-) benzothiazolyloxy methyl group, 2-[(2-, 4-, 5-, 6- or 7-) benzothiazolyloxy] ethyl group, 1-[(2-, 4 -, 5-, 6- or 7-) benzothiazolyloxy] ethyl group, 3-[(2-, 4-, 5-, 6- or 7-) benzothiazolyloxy] propyl group, 2- [(2-, 4-, 5-, 6- or 7-) benzothiazolyloxy] propyl group, 4-[(2-, 4-, 5-, 6- or 7-) benzothiazolyloxy A butyl group, 5-[(2-, 4-, 5-, 6- or 7-) benzothiazolyloxy] pentyl group, 4- [(4- -, 4-, 5-, 6- or 7-) benzothiazolyloxy] pentyl group, 6-[(2-, 4-, 5-, 6- or 7-) benzothiazolyloxy] hexyl group , 2-methyl-3-[(2-, 4-, 5-, 6- or 7-) benzothiazolyloxy] propyl group, 1,1-dimethyl-2-[(2-, 4-, 5 -, 6- or 7-) benzothiazolyloxy] ethyl group, 2- (2-methyl-5-benzothiazolyloxy) ethyl group, (2-methyl-5-benzothiazolyloxy) methyl group , 2- (4-ethyl-6-benzothiazolyloxy) ethyl group, (2-n-propyl-4-benzothiazolyloxy) methyl and the like, (5-tert-butyl-6-benzothiazolyl) Oxy) methyl group, (6-n-pentyl-7-benzothiazolyloxy) methyl group, 7-n-hexyl-5-benzothiazolyloxy) methyl group, 2- (2,4-dimethyl-5-benzothiazolyloxy) ethyl group, 2- (2,4,5-trimethyl-7-) Mentioning benzothiazolyloxy C1-6 alkyl groups such as a benzothiazolyloxy) ethyl group (1 to 3 C1-6 alkyl groups may be substituted on the benzothiazole ring) it can.

  Examples of the quinolyloxy C1-6 alkyl group (wherein at least one C1-6 alkyl group may be substituted on the quinoline ring) include, for example (2-, 3-, 4-, 5-, 6-, 7- or 8-) quinolyloxymethyl group, 2-[(2-, 3-, 4-, 5-, 6-, 7- or 8-) quinolyloxy] ethyl group, 1-[(2-, (2-) 3-, 4-, 5-, 6-, 7- or 8-) quinolyloxy] ethyl group, 3-[(2-, 3-, 4-, 5-, 6-, 7- or 8-) quinolyloxy] Propyl group, 2-[(2-, 3-, 4-, 5-, 6-, 7- or 8-) quinolyloxy] propyl group, 4-[(2-, 3-, 4-, 5-, 6 -, 7- or 8-) quinolyloxy] butyl group, 5-[(2-, 3-, 4-, 5-, 6-, 7- or 8-) quinolyloxy] pentyl , 4-[(2-, 3-, 4-, 5-, 6-, 7- or 8-) quinolyloxy] pentyl group, 6-[(2-, 3-, 4-, 5-, 6-, 7- or 8-) quinolyloxy] hexyl group, 2-methyl-3-[(2-, 3-, 4-, 5-, 6-, 7- or 8-) quinolyloxy] propyl group, 1, 1-dimethyl -2-[(2-, 3-, 4-, 5-, 6-, 7- or 8-) quinolyloxy] ethyl group, 2-methyl-8-quinolyloxymethyl group, (3-ethyl-7- Quinolyloxy) methyl group, (4-n-propyl-6-quinolyloxy) methyl group, (5-n-butyl-4-quinolyloxy) methyl group, (6-n-hexyl-5-quinolyloxy) methyl group, (2- Methyl-7-quinolyloxy) methyl group, (7-n-pentyl-6-quinolyloxy) Quinolyloxy C1 such as methyl group, (8-methyl-2-quinolyloxymethyl) group, (2,4-dimethyl-8-quinolyloxy) methyl group, (5, 6, 7-trimethyl-2-quinolyloxy) methyl group, etc. And 6 alkyl groups (1 to 3 C1-6 alkyl groups may be substituted on the quinoline ring) can be mentioned.

  2,3-dihydrobenzofuryloxy C1-6 alkyl group (on the 2,3-dihydrobenzofuran ring, at least one of a group selected from the group consisting of a C1-6 alkyl group and an oxo group is substituted As (2) may be, for example, (2-, 3-, 4-, 5-, 6- or 7-) 2,3-dihydrobenzofuryloxymethyl group, 2-[(2-, 3-, 4-; , 5-, 6- or 7-) 2,3-dihydrobenzofuryloxy] ethyl group, 1-[(2-, 3-, 4-, 5-, 6- or 7-) 2,3-dihydrobenzo Furyloxy] ethyl group, 3-[(2-, 3-, 4-, 5-, 6- or 7-) 2,3-dihydrobenzofuryloxy] propyl group, 2-[(2-, 3-, 4-, 5-, 6- or 7-) 2,3-dihydrobenzofuryloxy] propyl group, 4-[(4) -, 3-, 4-, 5-, 6- or 7-) 2,3-dihydrobenzofuryloxy] butyl group, 5-[(2-, 3-, 4-, 5-, 6- or 7- ) 2,3-Dihydrobenzofuryloxy] pentyl group, 4-[(2-, 3-, 4-, 5-, 6- or 7-) 2,3-dihydrobenzofuryloxy] pentyl group, 6- [6 (2-, 3-, 4-, 5-, 6- or 7-) 2,3-dihydrobenzofuryloxy] hexyl group, 2-methyl-3-[(2-, 3-, 4-, 5-] , 6- or 7-) 2,3-dihydrobenzofuryloxy] propyl group, 1,1-dimethyl-2-[(2-, 3-, 4-, 5-, 6- or 7-) 2, 3 -Dihydrobenzofuryloxy] ethyl group, 2- (2,2-dimethyl-7-2,3-dihydrobenzofuryloxy) ethyl group, (2,2- Methyl-7-2,3-dihydrobenzofuryloxy) methyl group, 2- (3-ethyl-6-2,3-dihydrobenzofuryloxy) ethyl group, (4-n-propyl-5-2,3-) Dihydrobenzofuryloxy) methyl group, (5-tert-butyl-6-2,3-dihydrobenzofuryloxy) methyl group, (6-n-pentyl-7-2,3-dihydrobenzofuryloxy) methyl group, (7-n-hexyl-5-2,3-dihydrobenzofuryloxy) methyl group, 2- (2,4-dimethyl-5-2,3-dihydrobenzofuryloxy) ethyl group, 2- (2,2 , 3-trimethyl-7-2,3-dihydrobenzofuryloxy) ethyl group, (2-oxo-5-2,3-dihydrobenzofuryloxy) methyl group, (3-oxo-6-2,3-dihydroben) 2,3-Dihydrobenzofuryloxy C1-6 alkyl group (2,3-dihydrobenzofuran ring such as Zofuryloxy) methyl group, (2-oxo-3-methyl-5-2,3-dihydrobenzofuryloxy) methyl group Above, a group selected from the group consisting of a C1-6 alkyl group and an oxo group may be substituted with 1 to 3).

1,2,3,4-Tetrahydronaphthyloxy C1-6 alkyl group (at least one oxo group may be substituted on the 1,2,3,4-tetrahydronaphthalene ring)
Are, for example, (1-, 2-, 5- or 6-) 1, 2, 3, 4-tetrahydronaphthyloxymethyl group, 2-[(1-, 2-, 5- or 6-) 1, 2,3,4-tetrahydronaphthyloxy] ethyl group, 1-[(1-, 2-, 5- or 6-) 1,2,3,4-tetrahydronaphthyloxy] ethyl group, 3-[(1- , 2-, 5- or 6-) 1,2,3,4-tetrahydronaphthyloxy] propyl group, 2-[(1-, 2-, 5- or 6-) 1,2,3,4-tetrahydro Naphthyloxy] propyl group, 4-[(1-, 2-, 5- or 6-) 1, 2, 3, 4-tetrahydronaphthyloxy] butyl group, 5-[(1-, 2-, 5- or 5 6-) 1,2,3,4-tetrahydronaphthyloxy] pentyl group, 4-[(1- or 2-) 1,2,3,3, -Tetrahydronaphthyloxy] pentyl group, 6-[(1- or 2-) 1,2,3,4-tetrahydronaphthyloxy] hexyl group, 2-methyl-3-[(1-, 2-, 5- or 6-) 1,2,3,4-tetrahydronaphthyloxy] propyl group, 1,1-dimethyl-2-[(1-, 2-, 5- or 6-) 1,2,3,4-tetrahydronaphthyl Oxy] ethyl group, [1-oxo- (2-, 5-, or 6-) 1, 2, 3, 4-tetrahydronaphthyloxy] methyl group, [1, 4-dioxo- (2-, 5- or 5- 6-) 1,2,3,4-tetrahydronaphthyloxy] methyl group, 1,2,4-trioxo- (3-, 5-, 6-, 7- or 8-) 1, 2, 3, 4- 1,2,3,4-Tetrahydronaphthy such as tetrahydronaphthyloxy] methyl group Oxy Cl to 6 (On 1,2,3,4-tetrahydronaphthalene ring, 1 to 3 oxo groups may be substituted) alkyl group can be exemplified.

  Examples of the 2,3-dihydro-1H-indenyloxy C1-6 alkyl group (wherein at least one oxo group may be substituted on the 2,3-dihydro-1H-indene ring) include, for example, (1-, 2-, 4- or 5-) 2,3-dihydro-1 H-indenyl oxymethyl group, 2-[(1-, 2-, 4- or 5-) 2,3-dihydro-1 H -Indenyloxy] ethyl group, 1-[(1-, 2-, 4- or 5-) 2,3-dihydro-1 H-indenyloxy] ethyl group, 3-[(1-, 2-, 4] -Or 5-) 2,3-dihydro-1H-indenyloxy] propyl group, 2-[(1-, 2-, 4- or 5-) 2,3-dihydro-1H-indenyloxy] propyl group , 4-[(1-, 2-, 4- or 5-) 2,3-dihydro-1 H-indenyloxy Butyl group, 5-[(1-, 2-, 4- or 5-) 2,3-dihydro-1H-indenyloxy] pentyl group, 4-[(1-, 2-, 4- or 5-) 2,3-Dihydro-1H-indenyloxy] pentyl group, 6-[(1-, 2-, 4- or 5-) 2,3-dihydro-1H-indenyloxy] hexyl group, 2-methyl- 3-[(1-, 2-, 4- or 5-) 2,3-dihydro-1 H-indenyloxy] propyl group, 1,1-dimethyl-2-[(1-, 2-, 4- or 5-) 2,3-dihydro-1H-indenyloxy] ethyl group, [1-oxo- (2-, 3-, 4-, 5-, 6- or 7-) 2,3-dihydro-1H- Indenyloxy] methyl group, [1, 3-dioxo- (2-, 4-, or 5-) 2,3-dihydro-1 H-indenylo 2,3-Dihydro-1H-indenyloxy C1-6 alkyl group such as a [] methyl group (one or two oxo groups may be substituted on the 2,3-dihydro-1H-indene ring Good) can be mentioned.

  Examples of the benzooxathiolanyloxy C1-6 alkyl group (in which at least one oxo group may be substituted on the benzooxathiolane ring) include, for example, (2-, 4-, 5-, 6) -Or 7-) benzooxathiolanyloxymethyl group, 2-[(2-, 4-, 5-, 6- or 7-) benzooxathiolanyloxy] ethyl group, 1-[(2-, 4-) , 5-, 6-, or 7-) benzooxathioranyloxy] ethyl group, 3-[(2-, 4-, 5-, 6- or 7-) benzooxathioranyloxy] propyl group, 2- [ (2-, 4-, 5-, 6-, or 7-) benzooxathiolanyloxy] propyl group, 4-[(2-, 4-, 5-, 6-, or 7-) benzooxathioranyloxy] Butyl group, 5-[(2-, 4-, 5-, 6- or 7-) benzoo Satioranyloxy] pentyl group, 4-[(2-, 4-, 5-, 6- or 7-) benzooxathioranyloxy] pentyl group, 6-[(2-, 4-, 5-, 6) -Or 7-) benzooxathiolanyloxy] hexyl group, 2-methyl-3-[(2-, 4-, 5-, 6- or 7-) benzooxathioranyloxy] propyl group, 1, 1- Dimethyl-2-[(2-, 4-, 5-, 6- or 7-) benzoxathioranyloxy] ethyl group, [2-oxo- (4-, 5-, 6- or 7-) benzoxa Mention may be made of benzooxathioranyloxy C1-6 alkyl groups such as a thioranyloxy] methyl group (on the benzooxathiolane ring, one oxo group may be substituted).

  The isoquinolyloxy C1-6 alkyl group is, for example, (1-, 3-, 4-, 5-, 6-, 7- or 8-) isoquinolyloxymethyl group, 2-[(1-, 3) -, 4-, 5-, 6-, 7- or 8-) isoquinolyloxy] ethyl group, 1-[(1-, 3-, 4-, 5-, 6-, 7- or 8-) Isoquinolyloxy] ethyl group, 3-[(1-, 3-, 4-, 5-, 6-, 7- or 8-) isoquinolyloxy] propyl group, 2-[(1-, 3- , 4-, 5-, 6-, 7- or 8-) isoquinolyloxy] propyl group, 4-[(1-, 3-, 4-, 5-, 6-, 7- or 8-) iso. Quinolyloxy] butyl group, 5-[(1-, 3-, 4-, 5-, 6-, 7- or 8-) isoquinolyloxy] pentyl group, 4-[(1-, 3-, 4-, 5-, 6-, 7- Is 8-) isoquinolyloxy! Pentyl group, 6-[(1-, 3-, 4-, 5-, 6-, 7- or 8-) isoquinolyloxy] hexyl group, 2-methyl-3 -[(1-, 3-, 4-, 5-, 6-, 7- or 8-) isoquinolyloxy] propyl group, 1, 1-dimethyl-2-[(1-, 3-, 4-] And 5-, 6-, 7- or 8-) isoquinolyloxy] ethyl group etc. can be mentioned.

  The pyridyloxy C1-6 alkyl group is, for example, (2-, 3- or 4-) pyridyloxymethyl group, 2-[(2-, 3- or 4-) pyridyloxy] ethyl group, 1-[( 2-, 3- or 4-) pyridyloxy] ethyl group, 3-[(2-, 3- or 4-) pyridyloxy] propyl group, 2-[(2-, 3- or 4-) pyridyloxy] Propyl group, 4-[(2-, 3- or 4-) pyridyloxy] butyl group, 5-[(2-, 3- or 4-) pyridyloxy] pentyl group, 4-[(2-, 3-) Or 4-) pyridyloxy] pentyl group, 6-[(2-, 3- or 4-) pyridyloxy] hexyl group, 2-methyl-3-[(2-, 3- or 4-) pyridyloxy] propyl Group, 1,1-dimethyl-2-[(2-, 3- or 4-) pyridyloxy It can be exemplified an ethyl group.

  As the dibenzofuryloxy C1-6 alkyl group, for example, (1-, 2-, 3- or 4-) dibenzofuryloxymethyl group, 2-[(1-, 2-, 3-, 4-, 5-) , 6-, 7- or 8-) dibenzofuryloxy! Ethyl group, 1-[(1-, 2-, 3- or 4-) dibenzofuryloxy] ethyl group, 3-[(1-, 2-) , 3- or 4-) dibenzofuryloxy] propyl group, 2-[(1-, 2-, 3- or 4-) dibenzofuryloxy] propyl group, 4-[(1-, 2-, 3- or 4-) Dibenzofuryloxy] butyl group, 5-[(1-, 2-, 3- or 4-) dibenzofuryloxy] pentyl group, 4-[(1-, 2-, 3- or 4-) dibenzo Furyloxy] pentyl group, 6-[(1-, 2-, 3- or 4-dibenzofuryloxy) Sil group, 2-methyl-3-[(1-, 2-, 3- or 4-) dibenzofuryloxy] propyl group, 1,1-dimethyl-2-[(1-, 2-, 3- or 4 -) Dibenzofuryloxy] ethyl group etc. can be mentioned.

  Examples of the 2H-1-benzopyranyloxy C1-6 alkyl group (wherein at least one oxo group may be substituted on the 2H-1-benzopyran ring) include, for example, (2-, 3-, -3, 4-, 5-, 6-, 7- or 8-) 2H-1-benzopyranyloxymethyl group, 2-[(2-, 3-, 4-, 5-, 6-, 7- or 8-) ) 2H-1-benzopyranyloxy] ethyl group, 1-[(2-, 3-, 4-, 5-, 6-, 7- or 8-) 2H-1-benzopyranyloxy] ethyl group, 3-[(2-, 3-, 4-, 5-, 6-, 7- or 8-) 2H-1-benzopyranyloxy] propyl group, 2-[(2-, 3-, 4-, 5-, 6-, 7- or 8-) 2H-1-benzopyranyloxy] propyl group, 4-[(2-, 3-, 4-, 5-, 6-, 7- or 8-) 2 -1-benzopyranyloxy! Butyl group, 5-[(2-, 3-, 4-, 5-, 6-, 7- or 8-) 2H-1-benzopyranyloxy] pentyl group, 4- [(2-, 3-, 4-, 5-, 6-, 7- or 8-) 2H-1-benzopyranyloxy] pentyl group, 6-[(2-, 3-, 4-, 5- , 6-, 7- or 8-) 2H-1-benzopyranyloxy] hexyl group, 2-methyl-3-[(2-, 3-, 4-, 5-, 6-, 7- or 8-) ) 2H-1-benzopyranyloxy] propyl group, 1,1-dimethyl-2-[(2-, 3-, 4-, 5-, 6-, 7- or 8-) 2H-1-benzopyrani 2H-l-benzopyra, such as roxy] ethyl group, [2-oxo- (3-, 4-, 5-, 6-, 7- or 8-) 2H- 1 -benzopyranyloxy] methyl group Aryloxy Cl to 6 (On 2H-1-benzopyran ring, one oxo group may be substituted) alkyl group can be exemplified.

  As the benzisoxazolyloxy C1-6 alkyl group, for example, (3-, 4-, 5-, 6- or 7-) benzisoxazolyloxymethyl group, 2-[(3-, 4 -, 5-, 6-, or 7-) benzisoxazolyloxy] ethyl group, 1-[(3-, 4-, 5-, 6-, or 7-) benzisoxazolyloxy] ethyl Group, 3-[(3-, 4-, 5-, 6-, or 7-) benzisoxazolyloxy] propyl group, 2-[(3-, 4-, 5-, 6-, or 7 -) Benzisoxazolyloxy] propyl group, 4-[(3-, 4-, 5-, 6-, or 7-) benzisoxazolyloxy] butyl group, 5-[(3-, 4 -, 5-, 6-, or 7-) benzoisoxazolyloxy! Pentyl group, 4-[(3-, 4-, 5-, 6-, or 7-) ben Isoxazolyloxy! Pentyl group, 6-[(3-, 4-, 5-, 6-, or 7-) benzisoxazolyloxy] hexyl group, 2-methyl-3-[(3-, 4-, 5-, 6-, or 7-) benzoisoxazolyloxy] propyl group, 1, 1-dimethyl-2-[(3-, 4-, 5-, 6-, or 7-) benzo Examples include isoxazolyloxy] ethyl group and the like.

  Examples of the benzofurazanyloxy C1-6 alkyl group include, for example, (4- or 5-) benzofurazanyloxymethyl group, 2-[(4- or 5-) benzofurazanyloxy] ethyl group, 1 -[(4- or 5-) benzofurazanyloxy] ethyl group, 3-[(4- or 5-) benzofurazanyloxy] propyl group, 2-[(4- or 5-) benzofuraza Nyloxy] propyl group, 4-[(4- or 5-) benzofurazanyloxy] butyl group, 5-[(4- or 5-) benzofurazanyloxy] pentyl group, 4-[(4- Or 5-) benzofurazanyloxy] pentyl group, 6-[(4- or 5-) benzofurazanyloxy] hexyl group, 2-methyl-3-[(4- or 5-) benzofurazanil Oxy] propyl group, 1,1-dimethyl-2-[(4- or 5) benzofuranyl The oxy] ethyl group and the like.

  As the quinoxalyloxy C1-6 alkyl group, for example, (2-, 5- or 6-) quinoxalyloxymethyl group, 2-[(2-, 5- or 6-) quinoxalyloxy] ethyl Group, 1-[(2-, 5- or 6-) quinoxalyloxy] ethyl group, 3-[(2-, 5- or 6-) quinoxalyloxy] propyl group, 2-[(2- , 5- or 6-) quinoxalyloxy] propyl group, 4-[(2-, 5- or 6-) quinoxalyloxy] butyl group, 5-[(2-, 5- or 6-) quino Xalyloxy] pentyl group, 4-[(2-, 5- or 6-) quinoxalyloxy] pentyl group, 6-[(2-, 5- or 6-) quinoxalyloxy] hexyl group, 2 -Methyl-3-[(2-, 5- or 6-) quinoxalyloxy] propyl group, 1,1-dimethyl 2 - [(2-, 5- or 6-) quinoxalyl oxy] can be exemplified an ethyl group.

  As C1-6 alkoxy C1-6 alkoxy substituted C1-6 alkyl group, for example, methoxymethoxymethyl, 2- (methoxymethoxy) ethyl, 1- (2-methoxyethoxy) ethyl, 1- (methoxymethoxy) ethyl, 2 -(3-propoxy) propoxyethyl, 3- (2-ethoxyisopropoxy) propyl, 4- (4-butoxybutoxy) butyl, 5- (5-pentyloxypentyloxy) pentyl, 6- (6-hexyloxyhexyl) Alkoxy moiety such as oxy) hexyl, 1,1-dimethyl-2- (ethoxymethoxy) ethyl, 2-methyl-3- (methoxyethoxy) propyl, 3- (propoxymethoxy) propyl group is a straight chain having 1 to 6 carbon atoms A linear or branched alkoxy group, the alkyl moiety of which is a linear or branched C1 to C6 carbon atom Examples include alkoxyalkoxyalkyl groups which are alkyl groups.

  Examples of the thienyl C1-6 alkoxy-substituted C1-6 alkyl group (wherein at least one halogen atom may be substituted on the thiophene ring) include, for example, a 2-thienylmethoxymethyl group and a 3-thienylmethoxymethyl group , 2- [2- (2-thienyl) ethoxy] ethyl group, 3- [3- (2-thienyl) propoxy] propyl group, 3- [3- (3-thienyl) propoxy] propyl group, 4- [4 -(2-thienyl) butoxy] butyl group, 4- [4- (3-thienyl) butoxy] butyl group, 5- [5- (2-thienyl) pentyloxy] pentyl group, 5- [5- (3-) Thienyl) pentyloxy] pentyl group, 6- [6- (2-thienyl) hexyloxy] hexyl group, 6- [6- (3-thienyl) hexyloxy] hexyl group, (5-chloro- -Thienylmethoxy) methyl group, (5-chloro-3-thienylmethoxy) methyl group, 2- [2- (4-bromo-2-thienyl) ethoxy] ethyl group, 3- [3- (3-fluoro-2) -Thienyl) propoxy] propyl group, 4- [4- (5-iodo-2-thienyl) butoxy] butyl group, 4- [4- (4-chloro-3-thienyl) butoxy] butyl group, 5- [5 -(3-chloro-2-thienyl) pentyloxy] pentyl group, 5-[(2-chloro-3-thienyl) methoxy] pentyl group, 6- [2- (3-chloro-2-thienyl) ethoxy] hexyl Group, 6- [6- (5-chloro-3-thienyl) hexyloxy] hexyl group, [2- (4,5-dichloro-2-thienyl) ethoxy] methyl group, [(2,4,5-trichloro) -3-thienyl) Thienylalkoxyalkyls in which the alkoxy moiety such as a toxi] methyl group is a linear or branched alkoxy group having 1 to 6 carbon atoms, and the alkyl moiety is a linear or branched alkyl group having 1 to 6 carbon atoms A group (on the thiophene ring, one to three halogen atoms may be substituted as a substituent) can be mentioned.

  Phenyl C2-6 alkenyloxy substituted C1-6 alkyl group (on the phenyl ring, selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group And at least one kind of the above-mentioned groups may be substituted) with unsubstituted or halogen-substituted or unsubstituted linear or branched alkyl group having 1 to 6 carbon atoms and halogen-substituted or unsubstituted A group selected from a linear or branched alkoxy group having 1 to 6 carbon atoms is preferably substituted by 1 to 5, preferably 1 to 3 phenyl groups, and at least a double bond having 2 to 6 carbon atoms. It is a group comprised from the alkenyl group which has 1-3, and phenyl C2-6 alkenyloxy group includes both a trans body and a cis body. As such phenyl C2-6 alkenyloxy C1-6 alkyl group, for example, (2-phenylvinyloxy) methyl group, (3-phenyl-2-propenyloxy) methyl group, 2- (4-phenyl-2) -Butenyloxy) ethyl group, 1- (4-phenyl-3-butenoxy) ethyl group, 3- (4-phenyl-1,3-butadienyloxy) propyl group, 4- (5-phenyl-1,3,3 5-hexatrienyloxy) butyl group, 5- [3- (2-fluorophenyl) -2-propenyloxy] pentyl group, 6- [3- (3-fluorophenyl) -2-propenyloxy] hexyl group, [3- (4-Fluorophenyl) -2-propenyloxy] methyl group, 2- [3- (2,3-difluorophenyl) -2-propenyloxy] ethyl group, -[3- (2,3,4,5,6-pentafluorophenyl) -2-propenyloxy] propyl group, 4- [3- (2,4-difluorophenyl) -2-propenyloxy] butyl group, 5- [3- (3,4-difluorophenyl) -2-propenyloxy] pentyl group, 6- [3- (3,5-difluorophenyl) -2-propenyloxy] hexyl group, [3- (2-) Chlorophenyl) -2-propenyloxy] methyl group, 2- [3- (3-chlorophenyl) -2-propenyloxy] ethyl group, 3- [3- (4-chlorophenyl) -2-propenyloxy] propyl group, 4 -[3- (2,3-dichlorophenyl) -2-propenyloxy] butyl group, 5- [3- (2,4-dichlorophenyl) -2-propenyloxy] pentyl group, 6- [6 -(3,4-dichlorophenyl) -2-propenyloxy] hexyl group, [3- (3,5-dichlorophenyl) -2-propenyloxy] methyl group, 2- [3- (2-bromophenyl) -2- group Propenyloxy] ethyl group, 3- [3- (3-bromophenyl) -2-propenyloxy] propyl group, 4- [3- (4-bromophenyl) -2-propenyloxy] butyl group, 5- [3 -(2-Methylphenyl) -2-propenyloxy] pentyl group, 6- [3- (3-methylphenyl) -2-propenyloxy] hexyl group, [3- (4-methylphenyl) -2-propenyloxy Methyl group, 2- [3- (2-trifluoromethylphenyl) -2-propenyloxy] ethyl group, 3- [3- (2-fluoro-4-bromophenyl) -2-pro Penyloxy] propyl group, 4- [3- (4-chloro-3-fluorophenyl) -2-propenyloxy] butyl group, 5- [3- (2,3,4-trichlorophenyl) -2-propenyloxy] Pentyl group, 6- [3- (2,4,6-trichlorophenyl) -2-propenyloxy] hexyl group, [3- (4-isopropylphenyl) -2-propenyloxy] methyl group, 2- [3- (4-n-Butylphenyl) -2-propenyloxy] ethyl group, 1- [3- (2,4-dimethylphenyl) -2-propenyloxy] ethyl group, 3- [3- (2,3-dimethyl) group Phenyl) -2-propenyloxy! Propyl group, [(2,6-dimethylphenyl) -2-propenyloxy] methyl group, 5- [3- (3,5-dimethylphenyl) -2-propenyl group [Oxy] pentyl group, 6- [3- (2,5-dimethylphenyl) -2-propenyloxy] hexyl group, [3- (2,4,6-trimethylphenyl) -2-propenyloxy] methyl group, [oxy 3- (3,5-ditrifluoromethylphenyl) -2-propenyloxy] methyl group, [3- (4-n-butoxyphenyl) -2-propenyloxy] methyl group, [3- (2,4-dimethoxyphen) Phenyl) -2-propenyloxy] methyl group, [3- (2,3-dimethoxyphenyl) -2-propenyloxy] methyl group, [3- (2,6-dimethoxyphenyl) -2-propenyloxy] methyl group , [3- (3,5-dimethoxyphenyl) -2-propenyloxy] methyl group, [3- (2,5-dimethoxyphenyl) -2-propenyloxy] methyl group [3- (3,5-ditrifluoromethoxyphenyl) -2-propenyloxy] methyl group, [3- (3-chloro-4-methoxyphenyl) -2-propenyloxy] methyl group, [3- (2- Chloro-4-trifluoromethoxyphenyl) -2-propenyloxy] methyl group, [3- (3-methyl-4-fluorophenyl) -2-propenyloxy] methyl group, [3- (4-bromo-3-) Trifluoromethylphenyl) -2-propenyloxy] methyl group, [3- (3-trifluoromethylphenyl) -2-propenyloxy] methyl group, [3- (4-trifluoromethylphenyl) -2-propenyloxy A methyl group, [3- (2-trifluoromethoxyphenyl) -2-propenyloxy] methyl group, [3- (3-trifluoromethoxy) methyl group, [2- (2-methoxyphenyl) -2-propenyloxy] methyl group, [3- (4-trifluoromethoxyphenyl) -2-propenyloxy] methyl group, [3- (2-methoxyphenyl) -2-propenyloxy] methyl group, 3- (3-methoxyphenyl) -2-propenyloxy] methyl group, [3- (4-methoxyphenyl) -2-propenyloxy] methyl group, [3- (3,4-dimethoxyphenyl) -2-propenyl group Oxy] methyl group, [3- (3,5-dimethoxyphenyl) -2-propenyloxy] methyl group, [4- (4-chlorophenyl) -2-butenyloxy] methyl group, [4- (4-chlorophenyl)- 3-butenyloxy] methyl group, [5- (4-chlorophenyl) -2-pentenyloxy] methyl group, [5- (4-chlorophenyl) -4- 4 And [6- (4-chlorophenyl) -5-hexenyloxy] methyl group, [6- (4-chlorophenyl) -4- 4- (4-chlorophenyl) -3-pentenyloxy] methyl group; Hexenyloxy] methyl group, [6- (4-chlorophenyl) -3-hexenyloxy] methyl group, [6- (4-chlorophenyl) -3- hexenyloxy] methyl group etc. can be mentioned.

  As the quinolyl C1-6 alkoxy-substituted C1-6 alkyl group, for example, (2-, 3-, 4-, 5-, 6-, 7- or 8-) quinolyl methoxymethyl group, 2- {2- [2 (2-, 3-, 4-, 5-, 6-, 7- or 8-) quinolyl] ethoxy} ethyl group, 3- {3-[(2-, 3-, 4-, 5-, 6- , 7- or 8-) quinolyl] propoxy} propyl group, 4- {4-[(2-, 3-, 4-, 5-, 6-, 7- or 8-) quinolyl] butoxy} butyl group, 5 -{5-[(2-, 3-, 4-, 5-, 6-, 7- or 8-) quinolyl] pentyloxy} pentyl group, 6- {6-[(2-, 3-, 4-] And an alkoxy moiety such as 5-, 6-, 7- or 8-) quinolyl] hexyloxy} hexyl group is a linear or branched alkoxy group having 1 to 6 carbon atoms, Alkyl moiety can be exemplified quinolyl alkoxyalkyl group is a straight-chain or branched alkyl group having 1 to 6 carbon atoms.

  As a piperidyl carbonyl C1-6 alkoxy substituted C1-6 alkyl group, for example, (1-, 2- or 3-) piperidyl carbonyl methoxymethyl group, 2- {2-[(1-, 2- or 3-) piperidyl] Carbonyl] ethoxy} ethyl group, 3- {3-[(1-, 2- or 3-) piperidinyl carbonyl] propoxy} propyl group, 4- {4-[(1-, 2- or 3-) piperidyl carbonyl] Butoxy} butyl group, 5- {5-[(1-, 2- or 3-) piperidinyl carbonyl] pentyloxy} pentyl group, 6- {6-[((1-, 2- or 3-) piperidyl carbonyl) And the alkoxy moiety such as a hexyloxy] hexyl group is a linear or branched alkoxy group having 1 to 6 carbon atoms, and the alkyl moiety is a linear or branched alkyl group having 1 to 6 carbon atoms It can be exemplified piperidylcarbonyl alkoxyalkyl group.

  Phenyl C2-10 alkenyl group [in the phenyl ring, a halogen atom, C1-4 alkylenedioxy group, C1-6 alkylthio group, benzoyl group, cyano group, nitro group, C2-6 alkanoyloxy group, C1 as a substituent group Group comprising an amino group, an hydroxyl group, a phenyl C1-6 alkoxy group, a phenoxy group, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group which may have an alkyl group of 6 to 6 As at least one kind of the selected group may be substituted], for example, a phenyl C 2-6 alkenyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C 1-6 alkyl group and At least one group selected from the group consisting of halogen-substituted or unsubstituted C1-6 alkoxy groups is substituted In addition to 2) n-pentyl-3-phenyl-2-propenyl group, 9-phenyl-2-nonenyl group, 10-phenyl-2-decenyl group, 8-phenyl-1,3 -Octadienyl group, 9-phenyl-1,3,5-nonatrienyl group, 10-2,4,6-decatrienyl group, 3- (4-methylthiophenyl) -2-propenyl group, 3- (3-methylthiophenyl) group -2-propenyl group, 3- (2-methylthiophenyl) -2-propenyl group, 3- (3,4-dimethylthiophenyl) -2-propenyl group, 3- (3,4,5-trimethylthiophenyl) -2-propenyl group, 3- (4-benzoyl) -2-propenyl group, 3- (3-benzoyl) -2-propenyl group, 3- (2-benzoyl) -2-propenyl group, 3- (3, 4 Dibenzoyl) -2-propenyl group, 3- (2,4,6-tribenzoyl) -2-propenyl group, 3- (4-cyanophenyl) -2-propenyl group, 3- (3-cyanophenyl) -2 -Propenyl group, 3- (2-cyanophenyl) -2-propenyl group, 3- (3,4-dicyanophenyl) -2-propenyl group, 3- (2,4,6-tricyanophenyl) -2- Propenyl group, 3- (4-acetyloxyphenyl) -2-propenyl group, 3- (4-acetyloxy-3-methoxyphenyl) -2-propenyl group, 3- (3-acetyloxyphenyl) -2-propenyl group Group, 3- (2-acetyloxyphenyl) -2-propenyl group, 3- (3,4-diacetyloxyphenyl) -2-propenyl group, 3- (2,4,6-triacetyloxyphene Nyl) -2-propenyl group, 3- (4-dimethylaminophenyl) -2-propenyl group, 3- (4-dimethylaminophenyl) -2-propenyl group, 3- (3-methylaminophenyl) -2- Propenyl group, 3- [2- (N-methyl-N-ethylamino) phenyl] -2-propenyl group, 3- (2,4-dimethylaminophenyl) -2-propenyl group, 3- [2,4,4 6-tri (dimethylamino) phenyl] -2-propenyl group, 3- (2-hydroxyphenyl) -2-propenyl group, 3- (3-hydroxyphenyl) -2-propenyl group, 3- (4-hydroxyphenyl) ) -2-propenyl group, 3- (3,5-dimethyl-4-hydroxyphenyl) -2-propenyl group, 3- (3-methoxy-4-hydroxyphenyl) -2-propenyl group 3- (2-hydroxyphenyl) -2-propenyl group, 3- (4-benzyloxyphenyl) -2-propenyl group, 3- (4-benzyloxyphenyl) -2-propenyl group, 3- (2-benzyl) Oxyphenyl) -2-propenyl group, 3- (2,4,6-tribenzyloxyphenyl) -2-propenyl group, 3- (3,4-dibenzyloxyphenyl) -2-propenyl group, 3- ( 4-phenoxyphenyl) -2-propenyl group, 3- (3-phenoxyphenyl) -2-propenyl group, 3- (2-phenoxyphenyl) -2-propenyl group, 3- (2,4-diphenoxyphenyl) -2-propenyl group, 3- (2,4,6-triphenoxyphenyl) -2-propenyl group, 3- (3,4-methylenedioxyphenyl) -2-propenyl group A phenyl group is 1 to 10 on a C2-10 alkenyl group such as 3- (2,3-ethylenedioxyphenyl) -2-propenyl group, 3- (3,4-ethylenedioxyphenyl) -2-propenyl group, etc. Examples thereof include a 2-substituted alkenyl group having 2 to 10 carbon atoms and 1 to 3 double bonds. The phenyl C2-10 alkenyl group includes both trans and cis forms. The phenyl ring has a halogen atom, a C1-4 alkylenedioxy group, a C1-6 alkylthio group, a benzoyl group, a cyano group, a nitro group, a C2-6 alkanoyloxy group, and a C1-6 alkyl group as a substituent. A group selected from the group consisting of amino group, hydroxyl group, phenyl C1-6 alkoxy group, phenoxy group, halogen substituted or unsubstituted C1-6 alkyl group and halogen substituted or unsubstituted C1-6 alkoxy group One to five, preferably one to three, may be substituted. When the substituent is a C1-4 alkylenedioxy group, it is preferable that the group is substituted by 1 to 2 on the phenyl ring.

  As a naphthyl C2-6 alkenyl group, for example, 2- (1- or 2-)-naphthylvinyl group, 3- (1- or 2-) naphthyl-2-propenyl group, 3- (1- or 2-) naphthyl group -2-methyl-2-propenyl group, 4- (1- or 2-) naphthyl-2-butenyl group, 4- (1- or 2-) naphthyl-3-butenyl group, 4- (1- or 2-) ) Naphthyl-1,3-butadienyl group, 5- (1- or 2-) naphthyl-1,3-pentadienyl group, 6- (1- or 2-) naphthyl-1,3-hexadienyl group, 6- (1 Naphthyl such as-or 2-) naphthyl-2-hexenyl group, 5- (1- or 2-) naphthyl-2-pentenyl group, 6- (1- or 2-) naphthyl-1,3,5-hexadienyl group Group-substituted C 2 to C 6 having 1 to 3 double bonds And an alkenyl group. The naphthyl C2-6 alkenyl group includes both trans and cis forms.

  Examples of the benzothienyl C 2-6 alkenyl group include, for example, 2- (2-, 3-, 4-, 5-, 6- or 7-) benzothienylvinyl group, 3- (2-, 3-, 4-, 4-, 5-, 6- or 7-) benzothienyl-2-propenyl group, 3- (2-, 3-, 4-, 5-, 6- or 7-) benzothienyl-2-methyl-2-propenyl group, 4- (2-, 3-, 4-, 5-, 6- or 7-) benzothienyl-2-butenyl group, 4- (2-, 3-, 4-, 5-, 6- or 7-) Benzothienyl-3-butenyl group, 4- (2-, 3-, 4-, 5-, 6-, or 7-) benzothienyl-1,3-butadienyl group, 5- (2-, 3-, 4-) , 5-, 6-, or 7-) benzothienyl-1,3-pentadienyl group, 6- (2-, 3-, 4-, 5-, 6- or 7-) benzothie 1, 3- (3-hexadienyl) group, 6- (2-, 3-, 4-, 5-, 6- or 7-) benzothienyl-2-hexenyl group, 5- (2-, 3-, 4-, 4- 5-, 6- or 7-) benzothienyl-2-pentenyl group, 6- (2-, 3-, 4-, 5-, 6- or 7-) benzothienyl-1,3,5-hexatrienyl Examples thereof include alkenyl groups having 2 to 6 carbon atoms and 1 to 3 double bonds which are substituted by a benzothienyl group such as a group. The benzothienyl C2-6 alkenyl group includes both trans and cis forms.

  Examples of the benzothiazolyl C 2-6 alkenyl group [at least one C 1-6 alkyl group may be substituted on the benzothiazole ring] include, for example, 2- (2-, 4-, 5-, 6-, Or 7-) benzothiazolyl vinyl group, 3- (2-, 4-, 5-, 6- or 7-) benzothiazolyl-2-propenyl group, 3- (2-, 4-, 5-, 6-) Or 7-) benzothiazolyl-2-methyl-2-propenyl group, 4- (2-, 4-, 5-, 6- or 7-) benzothiazolyl-2-butenyl group, 4- (2-, 4-, 5) -, 6 or 7-) benzothiazolyl-3-butenyl group, 4- (2-, 4-, 5-, 6- or 7-) benzothiazolyl-1,3-butadienyl group, 5- (2-, 4-) , 5-, 6- or 7-) benzothiazolyl-1,3-pentadienyl group 6- (2-, 4-, 5-, 6- or 7-) benzothiazolyl-1,3-hexadienyl group, 6- (2-, 4-, 5-, 6- or 7-) benzothiazolyl-2-hexenyl Group, 5- (2-, 4-, 5-, 6- or 7-) benzothiazolyl-2-pentenyl group, 6- (2-, 4-, 5-, 6- or 7-) benzothiazolyl-1, 3 5-hexadienyl group, 3- (2-methyl-5-benzothiazolyl) -2-propenyl group, 3- (2-ethyl-4-benzothiazolyl) -2-propenyl group, 3- (2-n-propyl-6) -Benzothiazolyl) -2-propenyl group, 3- (2-n-butyl-7-benzothiazolyl) -2-propenyl group, 3- (4-n-pentyl-5-benzothiazolyl) -2-propenyl group, 3- (4- (2-n-butyl-7-benzothiazolyl) -2-propenyl group 5-n-hexial-2-beta Benzothiazolyl such as zothiazolyl) -2-propenyl group, 3- (2,4-dimethyl-5-benzothiazolyl) -2-propenyl group, 3- (2,4,5-trimethyl-7-benzothiazolyl) -2-propenyl group and the like Examples thereof include alkenyl groups having 2 to 6 carbon atoms and 1 to 3 double bonds, which are substituted by a group. The benzothiazolyl C2-6 alkenyl group includes both a trans form and a cis form.

  A phenyl C1-6 alkyl group [on the phenyl ring a piperidyl group (on the piperidine ring at least one phenoxy group [on the phenyl ring a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and At least one of a group selected from the group consisting of a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted) and a phenoxy group (on the phenyl ring, halogen At least one group selected from the group consisting of an atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted As at least one kind of substituted groups are substituted], for example, 4- (1-piperidyl) benzyl group, 2,4-di (4-piperyl ) Benzyl, 2,4,6-tri (2-piperidyl) benzyl, 4- [4- (4-trifluoromethoxyphenoxy) -1-piperidyl] benzyl, 4- [4- (4-tri) Fluoromethylphenoxy) -1-piperidyl] benzyl group, 4- [4- (4-chlorophenoxy) -1-piperidyl] benzyl group, 4- {4- [3,4-di (trifluoromethoxy) phenoxy]- 1-piperidyl} benzyl group, 4- {4- [2,4,6-tri (trifluoromethyl) phenoxy] -1-piperidyl} benzyl group, 4- [4- (2,4-dichlorophenoxy) -1 -Piperidyl] benzyl group, 4- [4- (2,4,6-trifluorophenoxy) -1-piperidyl] benzyl group, 3- [2,4-diphenoxy-3-piperidyl] benzyl group, -[1,2,3-triphenoxy-4-piperidyl] benzyl group, 4- (4-trifluoromethoxyphenoxy) benzyl group, 4- (4-trifluoromethylphenoxy) benzyl group, 4- (4-chloro) Phenoxy) benzyl group, 4- (2,4-dichlorophenoxy) benzyl group, 4- (3,4,5-trifluorophenoxy) benzyl group, 4- (3-methylphenoxy) benzyl group, 4- (2- (2-methylphenoxy) benzyl group Methoxyphenoxy) benzyl group, 4- (2,4-dimethylphenoxy) benzyl group, 4- (3,4-dimethoxyphenoxy) benzyl group, 4- (2,4,6-trimethylphenoxy) benzyl group, 4- (4 3,4,5-Trimethoxyphenoxy) benzyl group, 2,4-diphenoxybenzyl group, 2,4,6-triphenoxybenzyl group, 2-phen Phenyl C1-6 alkyl groups such as noxy-4- (1-piperidyl) benzyl group [a phenyl ring on a phenyl ring (a piperidine ring on a piperidine ring [a halogen atom on a phenyl ring, halogen substituted or 1 to 5, preferably 1 to 3 groups selected from the group consisting of unsubstituted C1-6 alkyl groups and halogen-substituted or unsubstituted C1-6 alkoxy groups may be substituted Selected from the group consisting of three optionally substituted phenoxy groups (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group In which one to three groups selected from the group consisting of 1 to 5 and preferably 1 to 3 groups may be substituted.

  Diphenyl C1-6 alkyl group [in which at least one of a group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group on a phenyl ring] The species may be substituted], for example, diphenylmethyl group, 2,2-diphenylethyl group, 1,1-diphenylethyl group, 3,3-diphenylpropyl group, 2,3-diphenylpropyl group, 4,4-diphenylbutyl group, 5,5-diphenylpentyl group, 4,5-diphenylpentyl group, 6,6-diphenylhexyl group, 2-methyl-3,3-diphenylpropyl group, 1,1-dimethyl- 2,2-diphenylethyl group, di (4-chlorophenyl) methyl group, di (4-trifluoromethoxyphenyl) methyl group, di- 4-trifluoromethylphenyl) methyl group, di (3-methoxyphenyl) methyl group, di (2,4-dichlorophenyl) methyl group, di (2-methylphenyl) methyl group, di (2,4,6-tri) Fluorophenyl) methyl group, di (3,4-dimethoxyphenyl) methyl group, di (2,4,6-trimethoxyphenyl) methyl group, di (3,4-dimethylphenyl) methyl group, di (2,4 Phenyl groups such as 1,6-trimethylphenyl) methyl group, 1- (4-trifluoromethoxyphenyl) -1- (4-chlorophenyl) methyl group [a halogen atom, a halogen-substituted or unsubstituted C1 group on a phenyl ring, etc. 1 to 5, preferably 1 to 3 groups selected from the group consisting of an alkyl group of 6 to 6 and a halogen-substituted or unsubstituted C1-6 alkoxy group are substituted, Good] can be mentioned two substituted C1~6 alkyl group.

  A benzoyl C1-6 alkyl group (in which at least one of a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group on a phenyl ring The term “optionally substituted” refers to unsubstituted benzoyl C 1 -C 6 alkyl groups as well as halogen atoms on the phenyl rings making up these groups, and halogen-substituted or unsubstituted linear or branched C 1 A group in which 1 to 5, preferably 1 to 3 groups selected from the group consisting of an alkyl group of 6 to 6 and a halogen-substituted or unsubstituted linear or branched C1-6 alkoxy group are substituted For example, benzoylmethyl group, 1-benzoylethyl group, 2-benzoylethyl group, 3-benzoylpropyl group, 2-benzoylpropyl group, 4-be Zoylbutyl, 5-benzoylpentyl, 4-benzoylpentyl, 6-benzoylhexyl, 2-fluorobenzoylmethyl, 3-fluorobenzoylmethyl, 4-fluorobenzoylmethyl, 2-chlorobenzoylmethyl, 3 4-chlorobenzoylmethyl group, 4-chlorobenzoylmethyl group, 2-bromobenzoylmethyl group, 3-bromobenzoylmethyl group, 4-bromobenzoylmethyl group, 2-iodobenzoylmethyl group, 3-iodobenzoylmethyl group, 4- Iodobenzoylmethyl group, 2,3-difluorobenzoylmethyl group, 3,4-difluorobenzoylmethyl group, 3,5-difluorobenzoylmethyl group, 2,4-difluorobenzoylmethyl group, 2,6-difluorobenzoylmethyl group, 2,3-Diclo Benzoylmethyl group, 3,4-dichlorobenzoylmethyl group, 3,5-dichlorobenzoylmethyl group, 2,4-dichlorobenzoylmethyl group, 2,6-dichlorobenzoylmethyl group, 2-fluoro-4-bromobenzoylmethyl group 4-chloro-3-fluorobenzoylmethyl group, 2,3,4-trichlorobenzoylmethyl group, 3,4,5-trifluorobenzoylmethyl group, 2,4,6-trichlorobenzoylmethyl group, 4-isopropylbenzoyl Methyl group, 4-n-butyl benzoyl methyl group, 4-methyl benzoyl methyl group, 2-methyl benzoyl methyl group, 3- methyl benzoyl methyl group, 2,4- dimethyl benzoyl methyl group, 2,3- dimethyl benzoyl methyl group , 2,6-Dimethyl benzoyl methyl group, 3,5-dimethyl bene Nzoyl methyl group, 2,5-dimethyl benzoyl methyl group, 2,4,6-trimethyl benzoyl methyl group, 3,5-ditrifluoromethyl benzoyl methyl group, 2,3,4,5,6-pentafluoro benzoyl methyl group, 4-isopropoxybenzoylmethyl group, 4-n-butoxybenzoylmethyl group, 4-methoxybenzoylmethyl group, 2-methoxybenzoylmethyl group, 3-methoxybenzoylmethyl group, 2,4-dimethoxybenzoylmethyl group, 2, 3 -Dimethoxybenzoylmethyl group, 2,6-dimethoxybenzoylmethyl group, 3,5-dimethoxybenzoylmethyl group, 2,5-dimethoxybenzoylmethyl group, 2,4,6-trimethoxybenzoylmethyl group, 3,5-ditrile Fluoromethoxy benzoyl methyl group, 2-isopropo Benzoylmethyl group, 3-chloro-4-methoxybenzoylmethyl group, 2-chloro-4-trifluoromethoxybenzoylmethyl group, 3-methyl-4-fluorobenzoylmethyl group, 4-bromo-3-trifluoromethylbenzoyl group Methyl group, 2-trifluoromethylbenzoylmethyl group, 3-trifluoromethylbenzoylmethyl group, 4-trifluoromethylbenzoylmethyl group, 2-pentafluoroethyl benzoylmethyl group, 3-pentafluoroethyl benzoylmethyl group, 4- Pentafluoroethyl benzoyl methyl group, 2-trifluoro methoxy benzoyl methyl group, 3- trifluoro methoxy benzoyl methyl group, 4- trifluoro methoxy benzoyl methyl group, 2- pentafluoro ethoxy benzoyl methyl group, 3- pen Fluoroethoxybenzoylmethyl group, 4-pentafluoroethoxybenzoylmethyl group, 2- (2-trifluoromethylbenzoyl) ethyl group, 2- (3-trifluoromethylbenzoyl) ethyl group, 2- (4-trifluoromethylbenzoyl) group ) Ethyl group, 2- (2-trifluoromethoxybenzoyl) ethyl group, 2- (3-trifluoromethoxybenzoyl) ethyl group, 2- (4-trifluoromethoxybenzoyl) ethyl group, 2- (2-pentafluoro) Ethoxybenzoyl) ethyl group, 2- (3-pentafluoroethoxybenzoyl) ethyl group, 2- (4-pentafluoroethoxybenzoyl) ethyl group, 3- (2-trifluoromethylbenzoyl) propyl group, 3- (3- Trifluoromethyl benzoyl) propyl group, 3- (4-t) Trifluoromethylbenzoyl) propyl group, 3- (2-trifluoromethoxybenzoyl) propyl group, 3- (3-trifluoromethoxybenzoyl) propyl group, 3- (4-trifluoromethoxybenzoyl) propyl group, 3- (3- (4-trifluoromethoxybenzoyl) propyl group 3-pentafluoroethoxybenzoyl) propyl group, 3- (4-pentafluoroethoxybenzoyl) propyl group, 4- (3-pentafluoroethoxybenzoyl) butyl group, 5- (4-trifluoromethylbenzoyl) pentyl group, 4 -(4-trifluoromethylbenzoyl) pentyl group, 4- (4-trifluoromethoxybenzoyl) pentyl group, 6- (3-trifluoromethylbenzoyl) hexyl group, 6- (4-trifluoromethylbenzoyl) hexyl group , 6- (4-Trifluoromethoxybenzo Le) hexyl group, and the like.

  A C1-6 alkyl group, a C1-6 alkoxycarbonyl group and a phenyl C1-6 alkyl group [a phenyl group (a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group on a phenyl ring and Or at least one group selected from the group consisting of halogen-substituted or unsubstituted C1-6 alkoxy groups may be substituted), a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or At least one kind of groups selected from the group consisting of unsubstituted C1-6 alkoxy groups may be substituted] as an amino group which may be substituted at least one kind of groups selected from For example, amino group, tert-butoxycarbonylamino group, methylamino group, benzylamino group, (4-trifluorometh (Cybenzyl) amino group, (4-trifluoromethylbenzyl) amino group, (4-chlorobenzyl) amino group, [4- (4-trifluoromethoxyphenyl) benzyl] amino group, [4- (4-trifluoromethyl) Phenyl) benzyl] amino group, [4- (4-chlorophenyl) benzyl] amino group, N-methyl-N-benzylamino group, N-methyl-N- (4-trifluoromethoxybenzyl) amino group, N-methyl -N- (4-trifluoromethylbenzyl) amino group, N-methyl-N- (4-chlorobenzyl) amino group, N-methyl-N- [4- (4-trifluoromethoxyphenyl) benzyl] amino group N-methyl-N- [4- (4-trifluoromethylphenyl) benzyl] amino group, N-methyl-N- [4- (4-chlorophenyl) benzyl] Mino group, N-methoxycarbonyl-N-benzylamino group, N-ethoxycarbonyl-N- (4-trifluoromethoxybenzyl) amino group, N-propoxycarbonyl-N- (4-trifluoromethylbenzyl) amino group, N-n-butoxycarbonyl-N- (4-chlorobenzyl) amino group, N-n-pentyloxycarbonyl-N- [4- (4-trifluoromethoxyphenyl) benzyl] amino group, N-n-hexyloxy Carbonyl-N- [4- (4-trifluoromethylphenyl) benzyl] amino group, N-ethoxycarbonyl-N- [4- (4-chlorophenyl) benzyl] amino group, N, N-dimethylamino group, N- A linear or branched alkyl group having 1 to 6 carbon atoms such as methyl-N-ethylamino group, a linear or branched chain alkyl group having 1 to 6 carbon atoms And the alkyl moiety is a straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms [a phenyl group (a halogen atom on the phenyl ring, a halogen atom substituted or not substituted on the phenyl ring, 1 to 5, preferably 1 group selected from the group consisting of substituted C1-6 linear or branched alkyl groups and halogen substituted or unsubstituted C1-6 linear or branched alkoxy groups -3 optionally substituted), halogen atom, halogen-substituted or unsubstituted C1-6 linear or branched alkyl group, and halogen-substituted or unsubstituted C1-6 linear or branched alkoxy 1 to 5, preferably 1 to 3 groups selected from the group consisting of groups may be substituted] amino groups which may be substituted 1 to 2 groups selected from the group about It can be.

  A C1-6 alkyl group and a phenyl group (on the phenyl ring, a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group Examples of the amino C1-6 alkyl group which may be substituted by at least one group selected from the group consisting of at least one group which may be substituted) include, for example, aminomethyl group, 2-aminoethyl group, 1-aminoethyl group, 3-aminopropyl group, 4-aminobutyl group, 5-aminopentyl group, 6-aminohexyl group, 2-methyl-3-aminopropyl group, 1,1-dimethyl-2-aminoethyl Group, ethylaminomethyl group, 1- (propylamino) ethyl group, 2- (methylamino) ethyl group, 3- (isopropylamino) propyl group, 4- ( -Butylamino) butyl group, 5- (n-pentylamino) pentyl group, 6- (n-hexylamino) hexyl group, dimethylaminomethyl group, (N-ethyl-N-propylamino) methyl group, 2- ( N-methyl-Nn-hexylamino) ethyl group, phenylaminomethyl group, 1- (phenylamino) ethyl group, 2- (4-chloroanilino) ethyl group, 2- (4-trifluoromethoxyanilino) ethyl Group, 2- (4-trifluoromethylanilino) ethyl group, 3- (4-fluoroanilino) propyl group, 4- (3,4-difluoroanilino) butyl group, 5- (3,4,6 -Trifluoroanilino) pentyl, 6- (4-methylanilino) hexyl, (3-methoxyanilino) methyl, (2,3,4-trimethoxyanilino) methyl (3,4-dimethylanilino) methyl group, (2,4,6-trimethylanilino) methyl group, [N-ethyl-N- (3,4-dimethoxyanilino)] methyl group, 2- [N -Methyl-N- (4-chloroanilino)! Ethyl group, 2- [N-methyl-N- (4-trifluoromethoxyanilino)] ethyl group, 2- [N-methyl-N- (4-trifluoro) (Methylanilino)] C1-C6 straight-chain or branched-chain alkyl group such as ethyl group and phenyl group (on the phenyl ring, halogen atom, halogen-substituted or unsubstituted C1-C6 straight-chain or molecule 1 to 5, preferably 1 to 3 groups selected from the group consisting of a linear alkyl group and a halogen-substituted or unsubstituted C1-6 linear or branched alkoxy group may be substituted) One or two groups selected from the group Alkyl moiety can be mentioned an aminoalkyl group is a straight-chain or chain alkyl group having 1 to 6 carbon atoms.

  Benzofuryl C2-6 alkenyl group [in the benzofuran ring, at least one of the groups selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group The species may be substituted], for example, 2-[(2-, 3-, 4-, 5-, 6- or 7-) benzofuryl] vinyl group, 3-[(2-, 3- , 4-, 5-, 6- or 7-) benzofuryl] 2-propenyl group, 3-[(2-, 3-, 4-, 5-, 6- or 7-) benzofuryl] 2-methyl- 2-propenyl group, 4-[(2-, 3-, 4-, 5-, 6- or 7-) benzofuryl] -2-butenyl group, 4-[(2-, 3-, 4-, 5-] , 6- or 7-) benzofuryl] -3-butenyl group, 4-[(2-, 3-, 4-, 5-, 6 Or 7-) benzofuryl] -1,3-butadienyl group, 5-[(2-, 3-, 4-, 5-, 6- or 7-) benzofuryl] -1,3,5-hexatrienyl group, 5-[(2-, 3-, 4-, 5-, 6- or 7-) benzofuryl] -2,4-hexadienyl group, 5-[(2-, 3-, 4-, 5-, 6- Or 7-) benzofuryl] -3-pentenyl group, 3- [5-trifluoromethyl- (2-, 3-, 4-, 6- or 7-) benzofuryl] -2-propenyl group, 3- [5- Trifluoromethoxy- (2-, 3-, 4-, 6- or 7-) benzofuryl] -2-propenyl group, 3- [6-trifluoromethyl- (2-, 3-, 4-, 5- or 7-) Benzofuryl] -2-propenyl group, 3- [4-chloro- (2-, 3-, 5-, 6- or 7-) benzofuryl] -2-prope Group, 3- [4,5-dimethoxy- (2-, 3-, 6- or 7-) benzofuryl] -2-propenyl group, 3- [3,4,5-trimethyl- (2-, 6-) Or an alkenyl moiety such as 7-) benzofuryl] -2-propenyl group, 3- [3-methyl-5-methoxy- (2-, 4-, 6- or 7-) benzofuryl] -2-propenyl group has a carbon number Benzofuryl alkenyl group which is an alkenyl group having 2 to 6 straight or branched chain and having 1 to 3 double bonds and includes both a trans form and a cis form [on a benzofuran ring, a halogen atom, a halogen One to three substituted groups selected from the group consisting of substituted or unsubstituted C1-6 straight or branched chain alkyl groups and halogen substituted or unsubstituted C1 to 6 straight or branched chain alkoxy groups May be mentioned] That.

  [Piperidyl group [in the piperidine ring, at least one phenyl C.sub.2-6 alkenyl group (on the phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1-6 group. Examples of the group (1) in which at least one group selected from the group consisting of an alkoxy group may be substituted may be substituted with, for example, (1-, 2-, 3- or 4-) piperidyl group 1- (3-phenyl-2-propenyl)-(2-, 3- or 4-) piperidyl group, 1,3-di (3-phenyl-2-propenyl)-(2-, 4-, 5-) Or 6-) piperidyl group, 1, 2, 4- tri (3-phenyl-2-propenyl)-(3-, 5- or 6-) piperidyl group, 1- [3- (4-trifluoromethoxyphenyl) -2-propenyl]-( -, 3- or 4-) piperidyl group, 1- [3- (4-trifluoromethylphenyl) -2-propenyl]-(2-, 3- or 4-) piperidyl group, 1- [3- (4) -Chlorophenyl) -2-propenyl]-(2-, 3- or 4-) piperidyl group, 1- [3- (3,4-dimethoxyphenyl) -2-propenyl]-(2-, 3- or 4-) Piperidyl group such as piperidyl group, 1- [3- (2,4,6-trimethylphenyl) -2-propenyl]-(2-, 3- or 4-) piperidyl group [Piperidine ring A phenylalkenyl group (in which both of the trans form and the cis form are contained) in which the three above-mentioned alkenyl moieties are linear or branched alkenyl groups having 1 to 3 carbon atoms and 1 to 3 double bonds, and having 2 to 6 carbon atoms On the phenyl ring, halogen atoms, halogen substitution or 1 to 5, preferably 1 group selected from the group consisting of substituted C1-6 linear or branched alkyl groups and halogen substituted or unsubstituted C1-6 linear or branched alkoxy groups ~ 3 may be substituted) may be mentioned].

  As a ferrocene substituted C1-6 alkyl group, for example, ferrocene methyl group, 1-ferrocene ethyl group, 2-ferrocene ethyl group, 3-ferrocene propyl group, 2-ferrocene propyl group, 4-ferrocene butyl group, 5-ferrocene pentyl group A straight chain or a molecule having an alkyl moiety of 1 to 6 carbon atoms, such as a 4-ferrocene pentyl group, 6-ferrocene hexyl group, 1,1-dimethyl-2-ferrocene ethyl group and 2-methyl-3-ferrocene propyl group Examples thereof include ferrocene alkyl groups that are linear alkyl groups.

  Examples of the indolyl C1-6 alkyl group (wherein at least one halogen atom may be substituted on the indole ring) include, for example, [(1-, 2-, 3-, 4-, 5-, 6 -Or 7-) indolyl] methyl group, 1-[(1-, 2-, 3-, 4-, 5-, 6- or 7-) indolyl] ethyl group, 2-[(1-, 2-, 3-, 4-, 5-, 6- or 7-) indolyl] ethyl group, 3-[(1-, 2-, 3-, 4-, 5-, 6- or 7-) indolyl] propyl group, 2-[(1-, 2-, 3-, 4-, 5-, 6- or 7-) indolyl] propyl group, 4-[(1-, 2-, 3-, 4-, 5-, 6 -Or 7-) indolyl] butyl group, 5-[(1-, 2-, 3-, 4-, 5-, 6- or 7-) indolyl] pentyl group, 4-[(1-, 2-,- 3-, 4-, 5-, 6- or 7 ) Indolyl] pentyl group, 6-[(1-, 2-, 3-, 4-, 5-, 5- or 6- or 7-) indolyl] hexyl group, 1, 1-dimethyl-2-[(1-, 2) -, 3-, 4-, 5-, 6- or 7-) indolyl] ethyl group, 2-methyl-3-[(1-, 2-, 3-, 4-, 5-, 5- or 6- or 7- ) Indolyl] propyl group, [5-chloro- (1-, 2-, 3-, 4-, 6- or 7-) indolyl] methyl group, [5,6-difluoro- (1-, 2-, 3) -, 4- or 7-) indolyl] methyl group, [3, 5, 6- tribromo- (1-, 2-, 4- or 7-) indolyl] methyl group and the like alkyl moiety has 1 to 6 carbon atoms Examples include indolylalkyl groups which are linear or branched alkyl groups (1 to 3 halogen atoms may be substituted on the indole ring).

  As a phenyl C2-6 alkynyl group, for example, 2-phenylethynyl group, 3-phenyl-2-propynyl group, 3-phenyl-1-methyl-2-propynyl group, 4-phenyl-2-butynyl group, 4-phenyl-2-butynyl group A linear or molecular chain having 2 to 6 carbon atoms in the alkynyl moiety such as phenyl-3-butynyl group, 4-phenyl-1-butynyl group, 5-phenyl-2-pentynyl group, 6-phenyl-2-hexynyl group and the like And a phenyl alkynyl group which is a cyclic alkynyl group can be exemplified.

  Phenyl group [in the phenyl ring, C 1-4 alkylenedioxy group, phenyl group, C 1-6 alkoxycarbonyl group, hydroxyl group and phenoxy group (on the phenyl ring, halogen atoms, halogen substituted or unsubstituted C 1 to 6 At least one group selected from the group consisting of an alkyl group and at least one group selected from the group consisting of a halogen substituted or unsubstituted C1-6 alkoxy group For example, 4-biphenyl group, 4-tert-butoxycarbonylphenyl group, 4-ethoxycarbonylphenyl group, 2-biphenyl group, 4-hydroxyphenyl group, 4- (4-chlorophenoxy) Phenyl group, 2,3-ethylenedioxyphenyl group, 3-biphenyl group, 3-tert-butoxycarbonyl group Group, 3-methoxycarbonylphenyl group, 2,4-diphenylphenyl group, 3-hydroxyphenyl group, 4- (4-trifluoromethoxyphenoxy) phenyl group, 2,3-methylenedioxyphenyl group, 2,4 , 6-triphenyl group, 2-tert-butoxycarbonylphenyl group, 2-propoxycarbonylphenyl group, 2-n-pentyloxyphenyl group, 2-hydroxyphenyl group, 4- (4-trifluoromethylphenoxy) phenyl group 3,4-ethylenedioxyphenyl group, 2,4,6-trihydroxyphenyl group, 4-n-hexyloxycarbonylphenyl group, 2,4-diethoxycarbonylphenyl group, 2-biphenyl group, 3,4 -Dihydroxyphenyl group, 4- (2,4-dichlorophenoxy) phenyl group, 3- 2,4,6-trifluorophenoxy) phenyl group, 2,4,6-triethoxycarbonylphenyl group, 3- (2-methylphenoxy) phenyl group, 4- (3-methylphenoxy) phenyl group, 2- (2- (6-methylphenoxy) phenyl group 4-Methylphenoxy) phenyl group, 3- (2,3-dimethylphenoxy) phenyl group, 4- (2,4,5-trimethylphenoxy) phenyl group, 3- (2-methoxyphenoxy) phenyl group, 4- ( 3-methoxyphenoxy) phenyl group, 2- (4-methoxyphenoxy) phenyl group, 3- (3,4-dimethoxyphenoxy) phenyl group, 4- (2,4,6-trimethoxyphenoxy) phenyl group, 2- Phenyl groups such as phenoxy-4-ethoxycarbonylphenyl group, 2-phenyl-3-phenoxyphenyl group, etc. To 4 alkylenedioxy group, phenyl group, C1-6 alkoxycarbonyl group, hydroxyl group and phenoxy group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1 And 1 to 6 groups selected from the group consisting of 1 to 6 alkoxy groups, and 1 to 5 groups, preferably 1 to 3 groups, may be substituted) Can be mentioned.

  Examples of the benzofuryl group [optionally substituted on the benzofuran ring, at least one of a group selected from the group consisting of a halogen atom and a C1-6 alkyl group] include, for example, (2-, 3-, 4- , 5-, 6- or 7-) benzofuryl group, 5-chloro-7-benzofuryl group, 5-methyl-7-benzofuryl group, 4-iodo-6-benzofuryl group, 6-ethyl-7-benzofuryl group, 6 -Bromo-5-benzofuryl group, 7-n-propyl-4-benzofuryl group, 7-fluoro-2-benzofuryl group, 4-n-butyl-2-benzofuryl group, 2,5-dichloro-7-benzofuryl group, 5,6-Dimethyl-7-benzofuryl group, 3,5,6-trifluoro-2-benzofuryl group, 3,4,5-trimethyl-3-benzofuryl group, 5-chloro-4-methyl-7- Benzofuryl group such as nzofyl group, 5-methyl-3-fluoro-8-benzofuryl group [1 to 3 groups selected from the group consisting of a halogen atom and a C1-6 alkyl group are substituted on the benzofuran ring May be mentioned.

  Examples of the benzothiazolinyl group [at least one oxo group may be substituted on the benzothiazoline ring] include, for example, (2-, 4-, 5-, 6- or 7-) benzothiazolyl group And benzothiazolinyl groups such as 2-oxo-6-benzothiazolyl group [wherein one oxo group may be substituted on the benzothiazoline ring] can be mentioned.

  Examples of the benzothienyl group [at least one halogen atom may be substituted on the benzothiophene ring] include, for example, (2-, 3-, 4-, 5-, 6-, or 7-) benzo. Thienyl group, 5-fluoro-4-benzothienyl group, 6-fluoro-2-benzothienyl group, 2-chloro-3-benzothienyl group, 3-bromo-6-benzothienyl group, 4-iodo-5-benzo Benzothienyl groups such as thienyl group, 2,4,6-trichloro-7-benzothienyl group, 4,5-difluoro-2-benzothienyl group [1 to 3 halogen atoms are substituted on the benzothiophene ring May be mentioned].

  1,2,3,4-tetrahydroquinolyl group (wherein at least one group selected from the group consisting of oxo group and C1-6 alkyl group is substituted on the 1,2,3,4-tetrahydroquinoline ring And the like, for example, (1-, 2-, 3-, 4-, 5-, 6-, 7- or 8-) 1, 2, 3, 4-tetrahydroquinolyl group; Oxo- (1-, 3-, 4-, 5-, 6-, 7- or 8-) 1,2,3,4-tetrahydroquinolyl group, 2,4-dioxo- (1-, 3-, 5-, 6-, 7- or 8-) 1, 2, 3, 4-tetrahydroquinolyl group, 3-oxo- (1-, 2-, 4-, 5-, 6-, 7- or 8-) ) 1,2,3,4-tetrahydroquinolyl group, 1-methyl-2-oxo-5-1,2,3,4-tetrahydroquinolyl group, 2-methyl-1-1, , 3,4-tetrahydroquinolyl group, 3-ethyl-2-1,2,3,4-tetrahydroquinolyl group, 4-n-propyl-3-1,2,3,4-tetrahydroquinolyl group, 5-n-butyl-4-1,2,3,4-tetrahydroquinolyl group, 6-n-pentyl-5-1,2,3,4-tetrahydroquinolyl group, 7-n-hexyl-6- 1,2,3,4-tetrahydroquinolyl group, 8-methyl-7-1,2,3,4-tetrahydroquinolyl group, 4,6-dimethyl-5-1,2,3,4-tetrahydroquino group 1,2,3,4-Tetrahydroquinolyl groups (1,2,3,4-Tetrahydroquinolines such as silyl group, 5,6,7-trimethyl-4-1,2,3,4-tetrahydroquinolyl group On the ring, 1 group selected from the group consisting of oxo group and C1-6 alkyl group Three be substituted can be mentioned may also be).

  Examples of the 1,2-dihydrohydroquinolyl group (wherein at least one oxo group may be substituted on the 1,2-dihydrohydroquinoline ring) include, for example, (1-, 2-, 3-, 4-, 5-, 6-, 7- or 8-) 1,2-dihydrohydroquinolyl group, 2-oxo-1-, 3-, 4-, 5-, 6-, 7- or 8-) 1 Mention may be made of 1,2-dihydrohydroquinolyl groups such as, 2-dihydrohydroquinolyl group and the like.

  (One oxo group may be substituted on the 1,2-dihydrohydroquinoline ring) 1,2,3,4-tetrahydroquinazolinyl group [1,2,3,4-tetrahydroquinazoline Examples of the ring on which at least one member selected from the group consisting of oxo group and C1-6 alkyl group may be substituted include, for example, (1-, 2-, 3-, 4-, 5-, 6-, 7- or 8-) 1, 2, 3, 4-tetrahydroquinazolinyl group, 2-oxo- (1-, 3-, 4-, 5-, 6-, 7- or 8) -) 1,2,3,4-tetrahydroquinazolinyl group, 4-oxo- (1-, 2-, 3-, 5-, 6-, 7- or 8-) 1, 2, 3, 4- Tetrahydroquinazolinyl group, 2,4-dioxo- (1-, 3-, 5-, 6-, 7- or 8-) 1, 2, 3, 4-tetrahydroquina Rynyl group, 1-methyl-2,4-dioxo- (3-, 5-, 6-, 7- or 8-) 1,2,3,4-tetrahydroquinazolinyl group, 3-ethyl-2,4 -Dioxo- (1-, 5-, 6-, 7- or 8-) 1,2,3,4-tetrahydroquinazolinyl group, 1,3-dimethyl-2,4-dioxo (5-, 6- , 7- or 8-) 1,2,3,4-tetrahydroquinazolinyl group, 1-n-propyl-5-methyl-2-oxo- (3-, 4-, 6-, 7- or 8- ) 1,2,3,4-Tetrahydroquinazolinyl group, 1-n-butyl-6-methyl-4-oxo (2-, 3-, 5-, 7- or 8-) 1,2,3, 4-tetrahydroquinazolinyl group, 1-n-pentyl-7-methyl-2-oxo- (3-, 4-, 5-, 6- or 8-) 1, 2, 3, 4- tete Hydroquinazolinyl group, 1-n-hexyl-8-methyl-2,4-dioxo- (3-, 5-, 6- or 7-) 1, 2, 3, 4-tetrahydroquinazolinyl group, etc. 1 1,2,3,4-Tetrahydroquinazolinyl group [1,2,3,4-Tetrahydroquinazoline ring, one to four substituted groups selected from the group consisting of oxo group and C1-6 alkyl group May be mentioned].

  Examples of the benzothienyl-substituted C1-6 alkyl group [at least one halogen atom may be substituted on the benzothiophene ring] include, for example, 2-benzothienylmethyl group, 3-benzothienylmethyl group, 4 -Benzothienylmethyl group, 5-benzothienylmethyl group, 6-benzothienylmethyl group, 7-benzothienylmethyl group, 2- (2-benzothienyl) ethyl group, 3- (2-benzothienyl) propyl group, 4 -(2-benzothienyl) butyl group, 5- (2-benzothienyl) pentyl group, 6- (2-benzothienyl) hexyl group, 5-chloro-3-benzothienylmethyl group, 3,4-dibromo-2 Benzothienyl-substituted C.sub.1-6 alkyl groups such as -benzothienylmethyl group, 4,5,6-trichloro-2-benzothienylmethyl group, etc. On Zochiofen ring include a halogen atom may also be one to three substituents.

  As a naphthyl substituted C1-6 alkyl group, for example, 1-naphthylmethyl group, 2-naphthylmethyl group, 2- (1-naphthyl) ethyl group, 1- (2-naphthyl) ethyl group, 3- (1-naphthyl) group ) Propyl group, 3- (2-naphthyl) propyl group, 4- (1-naphthyl) butyl group, 4- (2-naphthyl) butyl group, 5- (1-naphthyl) pentyl group, 5- (2-naphthyl) group And pentyl), 6- (1-naphthyl) hexyl, 6- (2-naphthyl) hexyl and the like.

  Examples of the naphthyl-substituted C1-6 alkyl group (wherein at least one C1-6 alkoxy group may be substituted on the naphthalene ring) include, for example, [(1- or 2-) naphthyl] methyl group, 1 -[(1- or 2-) naphthyl] ethyl group, 2-[(1- or 2-) naphthyl] ethyl group, 3-[(1- or 2-) naphthyl] propyl group, 2-[(1- Or 2-) naphthyl] propyl group, 4-[(1- or 2-) naphthyl] butyl group, 5-[(1- or 2-) naphthyl] pentyl group, 4-[(1- or 2-) naphthyl group Pentyl group, 6-[(1- or 2-) naphthyl] hexyl group, 1,1-dimethyl-2-[(1- or 2-) naphthyl] ethyl group, 2-methyl-3-[(1- Or 2-) Naphthyl] propyl group, [6-methoxy- (1-, 2-, 3-, 4-, 5-, 7- or 8-) naphthi A methyl group, [5,6-dimethoxy- (1-, 2-, 3-, 4-, 7- or 8-) naphthyl] methyl group, [5, 6, 7-trimethoxy- (1-, 2-) A naphthyl-substituted alkyl group in which the alkyl moiety such as a 3-, 4- or 8-) naphthyl] methyl group is a linear or branched alkyl group having 1 to 6 carbon atoms And C 1 -C 6 linear or branched alkoxy groups may be substituted).

  Examples of pyridyl-substituted C1-6 alkyl group [wherein at least one halogen atom may be substituted on a pyridine ring] include, for example, 2-pyridylmethyl group, 3-pyridylmethyl group, 4-pyridylmethyl group , 2- (2-pyridyl) ethyl group, 2- (3-pyridyl) ethyl group, 2- (4-pyridyl) ethyl group, 3- (2-pyridyl) propyl group, 3- (3-pyridyl) propyl group , 3- (4-pyridyl) propyl group, 4- (2-pyridyl) butyl group, 4- (3-pyridyl) butyl group, 4- (4-pyridyl) butyl group, 5- (2-pyridyl) pentyl group , 5- (3-pyridyl) pentyl group, 5- (4-pyridyl) pentyl group, 6- (2-pyridyl) hexyl group, 6- (3-pyridyl) hexyl group, 6- (4-pyridyl) hexyl group , 2-chloro-3 Pyridylmethyl group, 3-bromo-2-pyridylmethyl group, 4-fluoro-2-pyridylmethyl group, 2- (2-chloro-4-pyridyl) ethyl group, 2- (3-chloro-5-pyridyl) ethyl group Group, 2- (4-iodo-3-pyridyl) ethyl group, 3- (2-bromo-5-pyridyl) propyl group, 3- (3-fluoro-4-pyridyl) propyl group, 3- (4-chloro) -2-pyridyl) propyl group, 4- (2-iodo-5-pyridyl) butyl group, 4- (3-bromo-5-pyridyl) butyl group, 4- (4-chloro-3-pyridyl) butyl group, 5- (2-chloro-5-pyridyl) pentyl group, 5- (3-fluoro-2-pyridyl) pentyl group, 5- (4-bromo-2-pyridyl) pentyl group, 6- (2-chloro-5) group -Pyridyl) hexyl group, 6- (3-) Oro-4-pyridyl) hexyl group, 6- (4-bromo-2-pyridyl) hexyl group, (2,6-dichloro-4-pyridyl) methyl group, (2,3,4-trichloro-6-pyridyl) Examples include pyridyl-substituted C1-6 alkyl groups such as methyl group [1 to 3 halogen atoms may be substituted as substituents on a pyridine ring].

  Examples of the furyl-substituted C1-6 alkyl group [wherein at least one nitro group may be substituted on the furan ring] include, for example, a 2-furylmethyl group, a 3-furylmethyl group, and 2- (2- (2-) Furyl) ethyl group, 3- (2-furyl) propyl group, 3- (3-furyl) propyl group, 4- (2-furyl) butyl group, 4- (3-furyl) butyl group, 5- (2- Furyl) pentyl group, 5- (3-furyl) pentyl group, 6- (2-furyl) hexyl group, 6- (3-furyl) hexyl group, 5-nitro-2-furyl methyl group, 5-nitro-3 -Furylmethyl group, 2- (5-nitro-2-furyl) ethyl group, 3- (5-nitro-2-furyl) propyl group, 4- (5-nitro-2-furyl) butyl group, 4- (4- 5-nitro-3-furyl) butyl group, 5- (5-nitro-2-yl) Pentyl group, 5- (5-nitro-3-furyl) pentyl group, 6- (5-nitro-2-furyl) hexyl group, 6- (5-nitro-3-furylhexyl) group, (4, Furyl-substituted C1-6 alkyl groups such as 5-dinitro-2-furyl) methyl group, (2,4,5-trinitro-3-furyl) methyl group [where a nitro group is substituted on the furan ring as a substituent) 3 may be substituted] can be mentioned.

  Examples of the thienyl-substituted C1-6 alkyl group [at least one halogen atom may be substituted on the thiophene ring] include, for example, 2-thienylmethyl group, 3-thienylmethyl group, 2- (2- (2-) Thienyl) ethyl group, 3- (2-thienyl) propyl group, 3- (3-thienyl) propyl group, 4- (2-thienyl) butyl group, 4- (3-thienyl) butyl group, 5- (2-thienyl) group Thienyl) pentyl group, 5- (3-thienyl) pentyl group, 6- (2-thienyl) hexyl group, 6- (3-thienyl) hexyl group, 5-chloro-2-thienylmethyl group, 5-chloro-3 -Thienylmethyl group, 2- (4-bromo-2-thienyl) ethyl group, 3- (3-fluoro-2-thienyl) propyl group, 4- (5-iodo-2-thienyl) butyl group, 4- (4-iodo-2-thienyl) group 4-chloro-3- -Yl) butyl group, 5- (3-chloro-2-thienyl) pentyl group, 5- (2-chloro-3-thienyl) pentyl group, 6- (3-chloro-2-thienyl) hexyl group, 6- (6) Thienyl-substituted C1-6 alkyl groups such as 5-chloro-3-thienyl) hexyl group, (4,5-dichloro-2-thienyl) methyl group, (2,4,5-trichloro-3-thienyl) methyl group One to three halogen atoms may be substituted as a substituent on the thiophene ring.

  As a phenyl group (on the phenyl ring, at least one of a group selected from the group consisting of a halogen atom and a halogen-substituted or unsubstituted C1-6 alkyl group may be substituted), for example, a phenyl group , 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 2-bromophenyl group, 3-bromophenyl group, 4-bromophenyl group Group, 2-iodophenyl group, 3-iodophenyl group, 4-iodophenyl group, 2,3-difluorophenyl group, 3,4-difluorophenyl group, 3,5-difluorophenyl group, 2,4-difluorophenyl group Group, 2,6-difluorophenyl group, 2,3-dichlorophenyl group, 3,4-dichlorophenyl group, 3,5 Dichlorophenyl group, 2,4-dichlorophenyl group, 2,6-dichlorophenyl group, 3,4,5-trifluorophenyl group, 3,4,5-trichlorophenyl group, 2,4,6-trifluorophenyl group, 2 , 4,6-trichlorophenyl group, 2-fluoro-4-bromophenyl group, 4-chloro-3-fluorophenyl group, 2,3,4-trichlorophenyl group, 3,4,5-trifluorophenyl group, 2,3,4,5,6-pentafluorophenyl group, 2,4,6-trimethylphenyl group, 4-n-butylphenyl group, 2,4-dimethylphenyl group, 2,3-dimethylphenyl group, 2 , 6-dimethylphenyl group, 3,5-dimethylphenyl group, 2, 5-dimethylphenyl group, 3,5-ditrifluoromethylphenyl group, 3-methyl-4-full Rophenyl group, 4-bromo-3-trifluoromethylphenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 2-methyl-3-chlorophenyl group, 3-methyl-4-chlorophenyl group , 2-chloro-4-methylphenyl group, 2-methyl-3-fluorophenyl group, 2-trifluoromethylphenyl group, 3-trifluoromethylphenyl group, 4-trifluoromethylphenyl group, 2-pentafluoroethyl Phenyl, 3-pentafluoroethylphenyl, 4-pentafluoroethylphenyl, 2-isopropylphenyl, 3-isopropylphenyl, 4-isopropylphenyl, 2-tert-butylphenyl, 3-tert-butyl Phenyl group, 4-tert-butylphenyl group, 2-sec- Butylphenyl group, 3-sec-butylphenyl group, 4-sec-butylphenyl group, 2-n-heptafluoropropylphenyl group, 3-n-heptafluoropropylphenyl group, 4-n-heptafluoropropylphenyl group, Examples include 4-n-pentylphenyl group, 4-n-hexylphenyl group, 2,3,4-trifluorophenyl group, 2,4,6-trifluorophenyl group and the like.

  A thiazolyl-substituted C1-6 alkyl group [on the thiazole ring is selected from the group consisting of a C1-6 alkyl group and a phenyl group (on the phenyl ring, a halogen atom and a halogen substituted or unsubstituted C1-6 alkyl group At least one kind of groups may be substituted) and at least one kind of groups selected from the group consisting of may be substituted], for example, 4-thiazolylmethyl group, 5-thiazolylmethyl group, 2- Methyl-4-thiazolylmethyl group, 2-methyl-5-thiazolylmethyl group, 2,5-dimethyl-4-thiazolylmethyl group, 2,4-dimethyl-5-thiazolylmethyl group, 2-methyl-5-phenyl-4-thiazolylmethyl group , 2-methyl-4-phenyl-5-thiazolylmethyl group, 2-phenyl-4-thiazolylmethyl group, 2-phenyl- -Thiazolylmethyl group, 2-phenyl-5-methyl-4-thiazolylmethyl group, 2-phenyl-4-methyl-5-thiazolylmethyl group, 2-methyl-5- (2-fluorophenyl) -4-thiazolylmethyl group, 2- Methyl-4- (2-fluorophenyl) -5-thiazolylmethyl group, 2- (2-chlorophenyl) -4-thiazolylmethyl group, 2- (2-bromophenyl) -5-thiazolylmethyl group, 2- (2-fluorophenyl) ) 5-Methyl-4-thiazolylmethyl group, 2- (2-fluorophenyl) -4-methyl-5-thiazolylmethyl group, 2-methyl-5- (3-iodophenyl) -4-thiazolylmethyl group, 2-methyl -4- (3-fluorophenyl) -5-thiazolylmethyl group, 2- (2,3-difluorophenyl) -4-thia Rylmethyl group, 2- (3-fluorophenyl) -5-thiazolylmethyl group, 2- (3-fluorophenyl) -5-methyl-4-thiazolylmethyl group, 2- (3-fluorophenyl) -4-methyl-5- Thiazolylmethyl group, 2-methyl-5- (2,4,6-trichlorophenyl) -4-thiazolylmethyl group, 2-methyl-4- (2,3,4,5,6-pentafluorophenyl) -5-thiazolylmethyl Group, 2- (4-fluorophenyl) -4-thiazolylmethyl group, 4- (2-fluorophenyl) -5-thiazolylmethyl group, 2- (4-fluorophenyl) -5-methyl-4-thiazolylmethyl group, 2- (4-fluorophenyl) -4-methyl-5-thiazolylmethyl group, 2-methyl-5- (2-chlorophenyl) -4-thiazolylmethyl group , 2-methyl-4- (2-chlorophenyl) -5-thiazolylmethyl group, 2- (2-chlorophenyl) -4-thiazolylmethyl group, 2- (2-chlorophenyl) -5-thiazolylmethyl group, 2- (2-chlorophenyl) group ) 5-Methyl-4-thiazolylmethyl group, 2- (2-chlorophenyl) -4-methyl-5-thiazolylmethyl group, 2-methyl-5- (3-chlorophenyl) -4-thiazolylmethyl group, 2-methyl-4 -(3-chlorophenyl) -5-thiazolylmethyl group, 2- (3-chlorophenyl) -4-thiazolylmethyl group, 2- (2-fluorophenyl) -5-thiazolylmethyl group, 2- (3-chlorophenyl) -5-methyl -4-thiazolyl methyl group, 2- (3-chlorophenyl) -4-methyl-5-thiazolyl methyl group, 2- 5- (4-chlorophenyl) -4-thiazolylmethyl group, 2-methyl-4- (4-chlorophenyl) -5-thiazolylmethyl group, 2- (4-chlorophenyl) -4-thiazolylmethyl group, 2- (4-chlorophenyl) -4-thiazolylmethyl group Chlorophenyl) -5-thiazolylmethyl group, 2- (4-chlorophenyl) -5-methyl-4-thiazolylmethyl group, 2- (4-chlorophenyl) -4-methyl-5-thiazolylmethyl group, 2- (2-thiazolyl) ethyl Group, 2- (4-thiazolyl) ethyl group, 2- (5-thiazolyl) ethyl group, 2- (2-methyl-4-thiazolyl) ethyl group, 2- (2-methyl-5-thiazolyl) ethyl group, 2- (2,5-dimethyl-4-thiazolyl) ethyl group, 2- (2,4-dimethyl-5-thiazolyl) ethyl group, 2- (2-methyl-5-pheny) -4-thiazolyl) ethyl group, 2- (2-methyl-4-phenyl-5-thiazolyl) ethyl group, 2- (2-phenyl-4-thiazolyl) ethyl group, 2- (2-phenyl-5-thiazolyl) ) Ethyl group, 2- (2-phenyl-5-methyl-4-thiazolyl) ethyl group, 3- (2-thiazolyl) propyl group, 2- (4-thiazolyl) propyl group, 3- (5-thiazolyl) propyl group Group, 3- (2-methyl-4-thiazolyl) propyl group, 2- (2-methyl-5-thiazolyl) propyl group, 3- (2,5-dimethyl-4-thiazolyl) propyl group, 3- (2 , 4-Dimethyl-5-thiazolyl) propyl, 3- (2-methyl-5-phenyl-4-thiazolyl) propyl, 3- (2-methyl-4-phenyl-5-thiazolyl) propyl, 2- (2-f Phenyl-4-thiazolyl) propyl group, 3- (3-phenyl-5-thiazolyl) propyl group, 3- (2-phenyl-5-methyl-4-thiazolyl) propyl group, 4- (2-thiazolyl) butyl group 4- (4-thiazolyl) butyl group, 3- (5-thiazolyl) butyl group, 4- (2-methyl-4-thiazolyl) butyl group, 4- (2-methyl-5-thiazolyl) butyl group, 4 -(2,5-dimethyl-4-thiazolyl) butyl group, 4- (2,4-dimethyl-5-thiazolyl) butyl group, 4- (2-methyl-5-phenyl-4-thiazolyl) butyl group, 4 -(2-methyl-4-phenyl-5-thiazolyl) butyl group, 4- (2-phenyl-4-thiazolyl) butyl group, 4- (4-phenyl-5-thiazolyl) butyl group, 4- (2- Phenyl-5-methyl 4-thiazolyl) butyl group, 5- (2-thiazolyl) pentyl group, 5- (4-thiazolyl) pentyl group, 5- (5-thiazolyl) pentyl group, 5- (2-methyl-4-thiazolyl) pentyl group 5- (2-methyl-5-thiazolyl) pentyl group, 5- (2,5-dimethyl-4-thiazolyl) pentyl group, 5- (2,4-dimethyl-5-thiazolyl) pentyl group, 5- (5- (2-methyl-5-thiazolyl) pentyl group; 2-methyl-5-phenyl-4-thiazolyl) pentyl group, 5- (2-methyl-4-phenyl-5-thiazolyl) pentyl group, 5- (2-phenyl-4-thiazolyl) pentyl group, 5- (5- (2-phenyl-4-thiazolyl) pentyl group; 4-phenyl-5-thiazolyl) pentyl group, 5- (2-phenyl-5-methyl-4-thiazolyl) pentyl group, 6- (2-thiazolyl) hexyl group, 6- (4-thiazolyl) hexyl group , 6- (5-thiazolyl) hexyl group, 6- (2-methyl-4-thiazolyl) hexyl group, 6- (2-methyl-5-thiazolyl) hexyl group, 6- (2,5-dimethyl-4-) Thiazolyl) hexyl group, 6- (2,4-dimethyl-5-thiazolyl) hexyl group, 6- (2-methyl-5-phenyl-4-thiazolyl) hexyl group, 6- (2-methyl-4-phenyl-) 5-thiazolyl) hexyl group, 6- (2-phenyl-4-thiazolyl) hexyl group, 6- (4-phenyl-5-thiazolyl) hexyl group, 6- (2-phenyl-5-methyl-4-thiazolyl) Hexyl group, 2- (2,3-dimethylphenyl) -4-thiazolylmethyl group, 2- (3-methylphenyl) -5-thiazolylmethyl group, 2- (3-trifluoromethylphenyl) -5-methyone Ru-4-thiazolylmethyl group, 2- (3-ethylphenyl) -4-methyl-5-thiazolylmethyl group, 2- (2-trifluoroethylphenyl) -4-methyl-5-thiazolylmethyl group, 2-methyl-5 A thiazolyl-substituted C1-6 alkyl group such as a-(2,4,6-trimethylphenyl) -4-thiazolylmethyl group [C1-6 alkyl group and phenyl group (a halogen atom and 1 to 5, preferably 1 to 3 groups selected from the group consisting of halogen-substituted or unsubstituted C1 to 6 alkyl groups may be selected from 1 to 2) And the like] may be mentioned.

  Examples of the tetrazolyl-substituted C1-6 alkyl group [at least one C1-6 alkyl group may be substituted on the tetrazole ring] include, for example, a 5- (1H) -tetrazolylmethyl group, 2- (5- (1H) -tetrazolyl) ethyl group, 1- (5- (1H) -tetrazolyl) ethyl group, 3- (5- (1H) -tetrazolyl) propyl group, 4- (5- (1H) -tetrazolyl ) Butyl group, 5- (5- (1H) -tetrazolyl) pentyl group, 6- (5- (1H) -tetrazolyl) hexyl group, 2-methyl-3- (5- (1H) -tetrazolyl) propyl group, 1,1-Dimethyl-2- (5- (1H) -tetrazolyl) ethyl group, 1-methyl-5- (1H) -tetrazolylmethyl group, 1-ethyl-5- (1H) -tetrazolylmethyl Group, 1-n-pro Le-5- (1H) -tetrazolylmethyl group, 1-n-butyl-5- (1H) -tetrazolylmethyl group, 1-n-pentyl-5- (1H) -tetrazolylmethyl group, 1-n-Hexyl-5- (1H) -tetrazolylmethyl group, 2- (1-methyl-5- (1H) -tetrazolyl) ethyl group, 2- (1-ethyl-5- (1H) -tetrazolyl ) Ethyl group, 2- (1-n-propyl-5- (1H) -tetrazolyl) ethyl group, 2- (1-n-butyl-5- (1H) -tetrazolyl) ethyl group, 2- (1-n) Tetrazolyl-substituted C1-6 alkyl group such as -pentyl-5- (1H) -tetrazolyl) ethyl group, 2- (1-n-hexyl-5- (1H) -tetrazolyl) ethyl group, etc. C 1 to 6 alkyl groups may be substituted] It can be mentioned.

  Examples of the isoxazolyl-substituted C1-6 alkyl group [at least one C1-6 alkyl group may be substituted on the isoxazole ring] include, for example, (3-, 4- or 5-isoxazolyl) methyl group , 2- (3-, 4- or 5-isoxazolyl) ethyl group, 1- (3-, 4- or 5- isoxazolyl) ethyl group, 3- (3-, 4- or 5- isoxazolyl) propyl group, 4 -(3-, 4- or 5- isoxazolyl) butyl group, 5- (3-, 4- or 5- isoxazolyl) pentyl group, 6- (3-, 4- or 5- isoxazolyl) hexyl group, 3- methyl -2- (3-, 4- or 5-isoxazolyl) propyl group, 1,1-dimethyl-2- (3-, 4- or 5-isoxazolyl) ethyl group, (3-methyl-4-isooone Sazolyl) methyl group, (4-ethyl-3-isoxazolyl) methyl group, (5-n-propyl-3-isoxazolyl) methyl group, (4-n-butyl-5-isoxazolyl) methyl group, (5-n- Pentyl-3-isoxazolyl) methyl group, (3-n-hexyl-4-isoxazolyl) methyl group, (3,4-dimethyl-5-isoxazolyl) methyl group, 2- (3-methyl-4-isoxazolyl) ethyl group 1- (4-ethyl-3-isoxazolyl) ethyl group, 3- (5-n-propyl-3-isoxazolyl) propyl group, 4- (4-n-butyl-5-isoxazolyl) butyl group, 5- (4- (4-n-butyl-5-isoxazolyl) butyl group 5-n-Pentyl-3-isoxazolyl) mepentyl group, 6- (3-n-hexyl-4-isoxazolyl) hexyl group, 2- (3, - [On isoxazole ring, Cl to 6 alkyl groups may be one or two substituted] isoxazolyl substituted Cl to 6 alkyl group such as dimethyl-5-isoxazolyl) ethyl group can be exemplified.

  1,2,4-oxadiazolyl-substituted C.sub.1-6 alkyl group [in the 1,2,4-oxadiazole ring, at least one phenyl group (C.sub.1-6 alkyl group is substituted on the phenyl ring. Optionally substituted) may be, for example, (3- or 5-) 1,2,4-oxadiazolylmethyl group, 2-[(3- or 5-) 1,2 2,4-oxadiazolyl] ethyl group, 1-[(3- or 5-) 1,2,4-oxadiazolyl] ethyl group, 3-[(3- or 5-) 1,2,4-oxadiazolyl] propyl group, 4-[(3- or 5-) 1,2,4-oxadiazolyl] butyl group, 5-[(3- or 5-) 1,2,4-oxadiazolyl] pentyl group, 6-[(3- or 5] -) 1,2,4-oxadiazolyl] hexyl group, 3-methyl-2- (3- or 5-) 1,2,4-oxadiazolyl] propyl group, 1,1-dimethyl-2-[(3- or 5-) 1,2,4-oxadiazolyl] ethyl group, (3-phenyl- 5-1,2,4-oxadiazolyl) methyl group, (5-phenyl-3-1,2,4-oxadiazolyl) methyl group, [3- (3-methylphenyl) -5-1,2,4-oxadiazolyl ] Methyl group, [5- (3,4-dimethylphenyl) -3-1,2,4-oxadiazolyl] methyl group, [3- (2,4,6-trimethylphenyl) -5-1,2 , 4-Oxadiazolyl] methyl group, [5- (2-ethylphenyl) -3-1,2,4-oxadiazolyl] methyl group, 2-[(3-n-propylphenyl) -5,1,2,4 -Oxadiazolyl] ethyl group, 1- [5 (4-n-Butylphenyl) -3-1,2,4-oxadiazolyl] ethyl group, 3- [3- (3-n-pentylphenyl) -5-1,2,4-oxadiazolyl]] propyl group, 4- [5- (5-n-hexylphenyl) -3-1,2,4-oxadiazolyl]] butyl group, 5- [3- (3-ethyl-4-methylphenyl) -5-1,2,4, 1,2,4-oxadiazolyl-substituted C1-6 alkyl group such as 4-oxadiazolyl]] pentyl group, 6- [5- (2-methylphenyl) -3-1,2,4-oxadiazolyl]] hexyl group [1 And one or more phenyl groups (C1 to C6 alkyl groups may be substituted one to three on the phenyl ring) may be substituted on the 2,4-oxadiazole ring Can be mentioned.

  Examples of the benzofurazanyl-substituted C1-6 alkyl group include, for example, 4-benzofurazanylmethyl, 5-benzofurazanylmethyl, 6-benzofurazanylmethyl, 7-benzofurazanylmethyl, 1- (4-benzofurazanil ) Ethyl, 2- (5-benzofurazanyl) ethyl, 3- (6-benzofurazanyl) propyl, 4- (7-benzofurazanyl) butyl, 5- (4-benzofurazanyl) pentyl, 6- (5-benzofurazanyl) hexyl, 2- Examples include methyl-3- (6-benzofurazanyl) propyl and 1,1-dimethyl-2- (7-benzofurazanyl) ethyl group.

  Phenylamino group [C-N-alkyl group may be substituted at the N-position of the phenylamino group, and at least one halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted on the phenyl ring of the phenylamino group May be substituted with unsubstituted phenylamino group (alias: anilino group) or phenylamino group substituted by 1 to 3 halogen substituted or unsubstituted C1-6 alkoxy groups as defined above For example, phenylamino group, 2-methoxyphenylamino group, 3-methoxyphenylamino group, 4-methoxyphenylamino group, 2-ethoxyphenylamino group, 3-ethoxyphenylamino group, 4-ethoxyphenylamino group , 4-n-propoxyphenylamino group, 4-tert-butoxyphenylamino group, 4-n-bu Xyphenylamino group, 2-trifluoromethoxylphenylamino group, 3-trifluoromethoxylphenylamino group, 4-trifluoromethoxyphenylamino group, 2-pentafluoroethoxyphenylamino group, 3-pentafluoroethoxyphenylamino group, 2,3-Dimethoxylphenylamino group, 3,4,5-trimethoxyphenylamino group, 4-n-pentyloxyphenylamino group, 4-n-hexyloxyphenylamino group, 3,5-ditrifluoromethoxyphenyl Amino group, N-phenyl-N-methylamino group, N- (2-methoxyphenyl) -N-ethylamino group, N- (3-methoxyphenyl) -N-n-propylamino group, N- (4-) Methoxyphenyl) -N-n-butylamino group, N- (2-ethoxyphenyl) N) pentylamino group, N- (3-ethoxyphenyl) -Nn-hexylamino group, N- (4-ethoxyphenyl) -N-methylamino group, N- (4-n-) Propoxyphenyl) -N-ethylamino group, N- (4-tert-butoxyphenyl) -N-n-propylamino group, N- (4-n-butoxyphenyl) -N-n-butylamino group, N- (2-trifluoromethoxyphenyl) -N-n-pentylamino group, N- (3-trifluoromethoxyphenyl) -N-n-hexylamino group, N- (4-trifluoromethoxyphenyl) -N-methyl Amino group, N- (2-pentafluoroethoxyphenyl) -N-ethylamino group, N- (3-pentafluoroethoxyphenyl) -Nn-propylamino group, N- (2,3-diamino) Methoxyphenyl) -N-methylamino group, N- (3,4,5-trimethoxyphenyl) -N-methylamino group, N- (4-n-pentyloxyphenyl) -N-methylamino group, N- Examples include (4-n-hexyloxyphenyl) -N-methylamino group, N- (3,5-ditrifluoromethoxyphenyl) -N-methylamino group and the like.

  Examples of the phenoxy group (a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted on the phenyl ring) include, for example, phenoxy group, 2-methoxyphenoxy group, 3-methoxyphenoxy group, 4- Methoxyphenoxy group, 4-isopropoxyphenoxy group, 4-n-butoxyphenoxy group, 2,4-dimethoxyphenoxy group, 2,3-dimethoxyphenoxy group, 2,3,4,5,6-pentamethoxyphenoxy group, 3,5-Dimethoxyphenoxy group, 2,5-dimethoxyphenoxy group, 2,4,6-trimethoxyphenoxy group, 3,5-di (trifluoromethoxy) phenoxy group, 4-methoxy-3-trifluoromethoxyphenoxy Group, 2,6-dimethoxyphenoxy group, 2-trifluoromethoxyphenoxy group, 3-trile Fluoromethoxy group, 4-trifluoromethoxyphenoxy group, 2,3-di (trifluoromethoxy) phenoxy group, 2,4-di (trifluoromethoxy) phenoxy group, 2-pentafluoroethoxyphenoxy group, 3- Pentafluoroethoxyphenoxy group, 4-pentafluoroethoxyphenoxy group, 2-isopropoxyphenoxy group, 3-isopropoxyphenoxy group, 4-isopropoxyphenoxy group, 2-tert-butoxyphenoxy group, 3-tert-butoxyphenoxy group , 4-tert-butoxyphenoxy group, 2-sec-butoxyphenoxy group, 3-sec-butoxyphenoxy group, 4-sec-butoxyphenoxy group, 4-n-hexyloxyphenoxy group, 2-n-heptafluoropropoxy phenoxy group And phenoxy groups such as 3-n-heptafluoropropoxyphenoxy group and 4-n-heptafluoropropoxyphenoxy group (on the phenyl ring, selected from the group consisting of halogen substituted or unsubstituted C1-6 alkoxy group 1 to 5 groups, and preferably 1 to 3 groups may be substituted).

  Amino group (on the amino group, a C1-6 alkyl group as a substituent and a phenyl group [a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1 6) at least one kind of groups selected from the group consisting of 6 alkoxy groups may optionally be substituted] Methylamino group, dimethylamino group, ethylamino group, diethylamino group, n-propylamino group, n-butylamino group, n-pentylamino group, 3-n-hexylamino group, phenylamino group, (4-chlorophenyl ) Amino group, (4-bromophenyl) amino group, (2,4-dichlorophenyl) amino group, (2,4,6-trichlorophenyl) Mino group, (2,3,4,5,6-pentafluorophenyl) amino group, (4-fluorophenyl) amino group, (4-iodophenyl) amino group, (4-chlorophenyl) amino group, (3- Methylphenyl) amino group, (4-trifluoromethylphenyl) amino group, (4-trifluoromethylphenyl) amino group, 3- (4-trifluoromethylphenyl) amino group, (3,4-dimethylphenyl) amino Group, (3,4,5-trimethylphenyl) amino group, (2-methoxyphenyl) amino group, (4-trifluoromethoxyphenyl) amino group, 3- (4-trifluoromethoxyphenyl) amino group, (3 5-Dimethoxyphenyl) amino group, (2,5-dimethoxyphenyl) amino group, (2,4,6-trimethoxyphenyl) amino Amino groups such as N-methyl-N- (4-trifluoromethylphenyl) amino group, N-ethyl-N- (4-trifluoromethoxyphenyl) amino group, etc. Alkyl group and phenyl group [in the phenyl ring, a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group is preferably And the group selected from the group consisting of 5 and preferably 1 to 3 may be substituted).

  Piperidyl group [on the piperidine ring, a phenoxy group (on the phenyl ring, a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted as a substituent group) and an amino group (on the amino group [C1-6 alkyl group as a substituent and a phenyl group [on the phenyl ring, selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group At least one group selected from the group consisting of at least one group selected from the group consisting of at least one group selected from the group consisting of at least one group selected from the group consisting of May be, for example, 2-piperidyl group, 3-piperidyl group, 4-piperidyl group, 2,4-diamino-1-piperidyl group, 2,4,6-tria No-1-piperidyl group, 4-amino-3-phenoxy-1-piperidyl group, 4-phenoxy-2-amino-1-piperidyl group, 2-amino-1-piperidyl group, 3-amino-1-piperidyl group , 4-amino-1-piperidyl group, 4-methylamino-1-piperidyl group, 4-ethylamino-1-piperidyl group, 4-n-propylamino-1-piperidyl group, 4-dimethylamino-1-piperidyl group Group, 4-diethylamino-1-piperidyl group, 4-di-n-propylamino-1-piperidyl group, 4-phenylamino-1-piperidyl group, 4- (N-phenyl-N-methylamino) -1-one Piperidyl group, 4- (2-fluorophenylamino) -1-piperidyl] group, 4- (3-fluorophenylamino) -1-piperidyl group, 4- (4-fluoro) Phenylamino) -1-piperidyl group, 4- (2-chlorophenylamino) -1-piperidyl group, 4- (3-chlorophenylamino) -1-piperidyl group, 4- (4-chlorophenylamino) -1-piperidyl group, 4- (2,3-dichlorophenylamino) -1-piperidyl group, 4- (2,4,6-trifluorophenylamino) -1-piperidyl group, 4- (2,4-dichlorophenylamino) -1-piperidyl Group, 4- (3,4-dichlorophenylamino) -1-piperidyl group, 4- (3,5-dichlorophenylamino) -1-piperidyl group, 4- (2,3,4,5,6-pentafluorophenyl) Amino) -1-piperidyl group, 4- (2-trifluoromethylphenylamino) -1-piperidyl group, 4- (2-methylphenylamino) -1- Piperidyl group, 4- (2,3-dimethylphenylamino) -1-piperidyl group, 4- (2-trifluoromethylphenylamino) -1-piperidyl group, 4- (2,4,6-trimethylphenylamino) -1-piperidyl group, 4- (4-trifluoromethylphenylamino) -1-piperidyl group, 4- (2-pentafluoroethylphenylamino) -1-piperidyl group, 4- (3-pentafluoroethylphenylamino ) -L-Piperidyl group, 4- (4-pentafluoroethylphenylamino) -1-piperidyl group, 4- (2-trifluoromethoxyphenylamino) -1-piperidyl group, 4- (2-methoxyphenylamino) -1-piperidyl group, 4- (2,3-dimethoxyphenylamino) -1-piperidyl group, 4- (2,4,6-trime Xyphenylamino) -1-piperidyl group, 4- [N-methyl-N- (2,4,6-trimethoxyphenylamino)]-1-piperidyl group, 4- [N-methyl-N- (3,, 4-Dimethylphenylamino)]-1-piperidyl group, 4- (3-trifluoromethoxyphenylamino) -1-piperidyl group, 4- (4-trifluoromethoxyphenylamino) -1-piperidyl group, 4- (4- (4-trifluoromethoxyphenylamino)) 2-pentafluoroethoxyphenylamino) -1-piperidyl group, 4- (3-pentafluoroethoxyphenylamino) -1-piperidyl group, 4- (4-pentafluoroethoxyphenylamino) -1-piperidyl group, 4- (4) (2-fluorophenylamino) -1-piperidyl group, 4- (3-fluorophenylamino) -1-piperidyl group, 4- (4-fluoro) Phenylamino) -1-piperidyl group, 4-phenoxy-1-piperidyl group, 2,4-diphenoxy-1-piperidyl group, 2,4,6-triphenoxy-1-piperidyl group, 4- (2-methoxyphenoxy) 1) 1-piperidyl group, 1- (3-methoxyphenoxy) -4-piperidyl group, 1- (4-methoxyphenoxy) -4-piperidyl group, 2- (2-ethoxyphenoxy) -3-piperidyl group, 3 -(3-Ethoxyphenoxy) -4-piperidyl group, 4- (4-ethoxyphenoxy) -5-piperidyl group, 3- (4-n-propoxyphenoxy) -2-piperidyl group, 2- (4-tert-) Butoxyphenoxy) -1-piperidyl group, 1- (4-n-butoxyphenoxy) -2-piperidyl group, 2- (2-trifluoromethoxyphenoxy) )) 3-piperidyl group, 3- (3-trifluoromethoxyphenoxy) -4-piperidyl group, 4- (4-trifluoromethoxyphenoxy) -3-piperidyl group, 3- (2-pentafluoroethoxyphenoxy)- 2-piperidyl group, 6- (3-pentafluoroethoxyphenoxy) -1-piperidyl group, 1- (2,3-dimethoxyphenoxy) -4-piperidyl group, 4- (3,4,5-trimethoxyphenoxy) group Piperidyl groups such as -1-piperidyl group, 4- (4-n-pentyloxyphenoxy group, 4- (4-n-hexyloxyphenoxy) -1-piperidyl group, etc. [Piperidine ring has a phenoxy group (phenyl ring In the above, one to five, preferably one to three halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted as a substituent. And an amino group (on the amino group, a C 1 to 6 alkyl group as a substituent and a phenyl group [on a phenyl ring, a halogen atom, a halogen substituted or unsubstituted C 1 to 6 alkyl group and a halogen substituted or unsubstituted 1 to 5 groups, preferably 1 to 3 groups, which may be substituted from the group consisting of C 1 to C 6 alkoxy groups; and 1 to 2 groups substituted from the group consisting of Groups selected from the group consisting of (1) may be substituted with 1 to 3 groups].

  Piperazinyl group [in the piperazine ring, a C1-6 alkoxycarbonyl group, a phenyl C1-6 alkyl group (in the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted At least one of a group selected from the group consisting of a C1-6 alkoxy group may be substituted, a phenyl C2-6 alkenyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6, At least one member selected from the group consisting of an alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted) and a benzoyl group (on the phenyl ring, a halogen atom, a halogen-substituted or an unsubstituted group) A group consisting of a substituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group At least one kind of the group selected from the group consisting of at least one kind of the selected groups may be substituted], for example, (1-, 2- or 3) -) Piperazinyl group, 4-tert-butoxycarbonyl-1-piperazinyl group, 4-ethoxycarbonyl-1-piperazinyl group, 4-methoxycarbonyl-1-piperazinyl group, 2,4-dimethoxycarbonyl-1-piperazinyl group, 2 4,6-triethoxycarbonyl-1-piperazinyl group, 4- (4-trifluoromethoxybenzyl) -1-piperazinyl group, 4- (4-chlorobenzyl) -1-piperazinyl group, 4- (4-methoxy) Benzyl) -1-piperazinyl group, 4- (4-bromobenzyl) -1-piperazinyl group, 4- (4-methylbenzyl) -1-piperazy And 4- (2,4-dichlorobenzyl) -1-piperazinyl, 4- (3,4-dimethoxybenzyl) -1-piperazinyl, 4- (2,4,6-trifluorobenzyl) -1 -Piperazinyl group, 4- (3,4-dimethylbenzyl) -1-piperazinyl group, 4- (2,4,6-trimethoxybenzyl) -1-piperazinyl group, 4- (2,4,6-trimethylbenzyl) )-1-Piperazinyl group, 4- (4-iodobenzyl) -1-piperazinyl group, 4- (4-trifluoromethylbenzyl) -1-piperazinyl group, 4- (3,4-dichlorobenzyl) -1- Piperazinyl group, 4- [3- (4-trifluoromethylphenyl) -2-propenyl] -1-piperazinyl group, 4- [3- (4-trifluoromethylphenyl) -2-propenyl] -1 -Piperazinyl group, 4- (4-trifluoromethylbenzoyl) -1-piperazinyl group, 4- [3- (4-chlorophenyl) -2-propenyl] -1-piperazinyl group, 4- [3- (4-methyl) Phenyl) -2-propenyl] -1-piperazinyl group, 4- [3- (4-methoxyphenyl) -2-propenyl] -1-piperazinyl group, 4- [3- (3,4-dimethylphenyl) -2 -Propenyl] -1-piperazinyl group, 4- [3- (3,4-dimethoxyphenyl) -2-propenyl] -1-piperazinyl group, 4- [3- (3,4,5-trimethylphenyl) -2 -Propenyl] -1-piperazinyl group, 4- [3- (3,4,5-trimethoxyphenyl) -2-propenyl] -1-piperazinyl group, 4- [3- (3,4-dichlorophenyl)- -Propenyl] -1-piperazinyl group, 4- [3- (2,4,6-trifluorophenyl) -2-propenyl] -1-piperazinyl group, 4- [3- (4-iodophenyl) -2-] Propenyl] -1-piperazinyl group, 4- [3- (3-bromophenyl) -2-propenyl] -1-piperazinyl group, 4- (4-fluorobenzyl) -1-piperazinyl group, 4- (4-methyl) Benzoyl) -1-piperazinyl group, 4- (4-methoxybenzoyl) -1-piperazinyl group, 4- (3,4-dimethylbenzoyl) -1-piperazinyl group, 4- (2,4-dimethoxybenzoyl) -1 -Piperazinyl group, 4- (3,4,5-trimethylbenzoyl) -1-piperazinyl group, 4- (2,4,6-trimethoxybenzoyl) -1-piperazinyl group, 4- (4- -Chlorobenzoyl) -1-piperazinyl group, 4- (2,4,6-trifluorobenzoyl) -1-piperazinyl group, 4- (4-bromobenzoyl) -1-piperazinyl group, 4- (4-iodobenzoyl group) ) -L-piperazinyl group, 4- (3,4-dichlorobenzoyl) -1-piperazinyl group, 4- (4-fluorobenzoyl) -1-piperazinyl group, 4-benzyl-3- (3-phenyl-2-) Piperazinyl groups such as propenyl) -1-piperazinyl group, 4-benzoyl-3,5-dibenzyl-1-piperazinyl group [C.sub.1-6 alkoxycarbonyl group on the piperazine ring, phenyl C.sub.1-6 alkyl group (on the phenyl ring A halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group. Group selected from the group consisting of 1 to 5 groups, which may be substituted, preferably 1 to 3), phenyl C 2-6 alkenyl group (unsubstituted or halogen atom, halogen substituted or unsubstituted C 1 to C 6 And 6 selected from 1 to 2 and preferably 1 to 3 substituted phenyl groups each selected from 6 alkyl groups and halogen-substituted or unsubstituted C1-6 alkoxy groups, each having 1 to 2 carbon atoms and 2 to 6 carbon atoms; It is a group composed of an alkenyl group having 1 to 3 bonds. And 1 to 5 groups selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group on the phenyl ring) , And preferably 1 to 3 groups may be substituted), and groups selected from the group consisting of 1 to 3 may be substituted].

  Homopiperazinyl group [in a homopiperazine ring, a C.sub.1-6 alkoxycarbonyl group and a phenyl C.sub.1-6 alkyl group (in a phenyl ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted At least one kind of groups selected from the group consisting of C1-6 alkoxy groups of at least one kind of groups selected from the group consisting of , (1-, 2-, 3-, 4-, 5-, 6- or 7-) homopiperazinyl group, 3,4-dibenzyl-1-homopiperazinyl group, 2,7-dibenzyl-1-homopiperazinyl group, 2, 3,4-Tribenzyl-1-homopiperazinyl, 2,4,6-tribenzyl-1-homopiperazinyl, 4-benzyl-1-homopiperazinyl 4- (2-phenethyl) -1-homopiperazinyl group 4- (3-phenylpropyl) -1-homopiperazinyl group 4- (4-phenylbutyl) -1-homopiperazinyl group 4- (5-phenylpentyl) -1-homopiperazinyl group, 4- (6-phenylhexyl) -1-homopiperazinyl group, 4- (2-fluorobenzyl) -1-homopiperazinyl group, 4- (3-fluorobenzyl) -1-homopiperazinyl group, 4- (3-fluorobenzyl) -1-homopiperazinyl group (4-fluorobenzyl) -1-homopiperazinyl group, 4- (2-chlorobenzyl) -1-homopiperazinyl group, 4- (3-chlorobenzyl) -1-homopiperazinyl group, 4- (4-chlorobenzyl) -1 -Homopiperazinyl group, 4- (2,3-dichlorobenzyl) -1-homopiperazinyl group, 4- (2,4-dichloromethane group) Jyl) -1-homopiperazinyl group, 4- (3,4-dichlorobenzyl) -1-homopiperazinyl group, 4- (3,5-dichlorobenzyl) -1-homopiperazinyl group, 4- (3,4,5-trichloro) Benzyl) -1-homopiperazinyl group, 4- (2,3,4,5,6-pentafluorobenzyl) -1-homopiperazinyl group, 4- (2-trifluoromethylbenzyl) -1-homopiperazinyl group, 4- (2-) 3-trifluoromethylbenzyl) -1-homopiperazinyl group, 4- (4-trifluoromethylbenzyl) -1-homopiperazinyl group, 4- (4-methylbenzyl) -1-homopiperazinyl group, 4- (3,4-) Dimethylbenzyl) -1-homopiperazinyl group, 4- (2,4,6-trimethylbenzyl) -1-homopiperazinyl group, 4- (2-pe Intafluoroethylbenzyl) -1-homopiperazinyl, 4- (3-pentafluoroethylbenzyl) -1-homopiperazinyl, 4- (4-pentafluoroethylbenzyl) -1-homopiperazinyl, 4- (2-trifluoro) benzyl. Methoxybenzyl) -1-homopiperazinyl group, 4- (3-trifluoromethoxybenzyl) -1-homopiperazinyl group, 4- (4-trifluoromethoxybenzyl) -1-homopiperazinyl group, 4- (4-methoxybenzyl)- 1-homopiperazinyl group, 4- (3,4-dimethoxybenzyl) -1-homopiperazinyl group, 4- (2,4,6-trimethoxybenzyl) -1-homopiperazinyl group, 4- (2-pentafluoroethoxybenzyl) -1-homopiperazinyl group, 4- (3-pentafluoroethoxy bene) Jyl) -1-homopiperazinyl group, 4- (4-pentafluoroethoxybenzyl) -1-homopiperazinyl group, 4- [2- (4-trifluoromethoxyphenyl) ethyl] -1-homopiperazinyl group, 4- [3- (4-Trifluoromethoxyphenyl) propyl] -1-homopiperazinyl, 4- [4- (4-trifluoromethoxyphenyl) butyl] -1-homopiperazinyl, 4- [5- (4-trifluoromethoxyphenyl) Pentyl] -1-homopiperazinyl group, 4- [6- (4-trifluoromethoxyphenyl) hexyl] -1-homopiperazinyl group, 4- [2- (4-trifluoromethylphenyl) ethyl] -1-homopiperazinyl group, 4- [3- (4-trifluoromethylphenyl) propyl] -1-homopiperazinyl group, -[4- (4-Trifluoromethylphenyl) butyl] -1-homopiperazinyl group, 4- [5- (4-trifluoromethylphenyl) pentyl] -1-homopiperazinyl group, 4- [6- (4-tri-tributyl] butyl group Fluoromethylphenyl) hexyl] -1-homopiperazinyl group, 4-tert-butoxycarbonyl- (1-, 2-, 3-, 5-, 6- or 7-) homopiperazinyl group, 4-methoxycarbonyl (1-, 2 -, 3-, 5-, 6- or 7-) homopiperazinyl group, 4-ethoxycarbonyl carbonyl- (1-, 2-, 3-, 5-, 6- or 7-) homopiperazinyl group such as homopiperazinyl group [homo On the piperazine ring, a C1 to 6 alkoxycarbonyl group and a phenyl C1 to 6 alkyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted group 1-5, preferably 1 to 3 groups selected from the group consisting of substituted C1-6 alkyl groups and halogen-substituted or unsubstituted C1-6 alkoxy groups; One to three selected groups may be substituted].

  As the phenoxy substituted phenyl group (on the phenyl ring, at least one halogen substituted or unsubstituted C1-6 alkoxy group may be substituted), for example, 2-phenoxyphenyl group, 2,3-di Phenoxyphenyl group, 2,4,6-triphenoxyphenyl group, 3- (2-methoxyphenoxy) phenyl group, 4- (3-methoxyphenoxy) phenyl group, 2- (4-methoxyphenoxy) phenyl group, 3- (4-isopropoxyphenoxy) phenyl group, 4- (4-n-butoxyphenoxy) phenyl group, 2- (2,4-dimethoxyphenoxy) phenyl group, 3- (2,3-dimethoxyphenoxy) phenyl group, 4 -(2,3,4,5,6-pentamethoxyphenoxy) phenyl group, 2- (3,5-dimethoxyphenoxy) pheny Group, 3- (2,5-dimethoxyphenoxy) phenyl group, 4- (2,4,6-trimethoxyphenoxy) phenyl group, 2- [3,5-di (trifluoromethoxy) phenoxy] phenyl group, 3 -(4-methoxy-3-trifluoromethoxyphenoxy) phenyl group, 4- (2,6-dimethoxyphenoxy) phenyl group, 2- (2-trifluoromethoxyphenoxy) phenyl group, 3- (3-trifluoromethoxy Phenoxyphenyl group, 4- (4-trifluoromethoxyphenoxy) phenyl group, 2- [2,3-di (trifluoromethoxy) phenoxy] phenyl group, 3- [2,4-di (trifluoromethoxy) phenoxy] Phenyl group, 4- (2-pentafluoroethoxyphenoxy) phenyl group, 2- (3-pentafluoroethoxy) phenyl group Noxy) phenyl group, 3- (4-pentafluoroethoxyphenoxy) phenyl group, 4- (2-isopropoxyphenoxy) phenyl group, 2- (3-isopropoxyphenoxy) phenyl group, 3- (4-isopropoxyphenoxy) ) Phenyl group, 4- (2-tert-butoxyphenoxy) phenyl group, 2- (3-tert-butoxyphenoxy) phenyl group, 3- (4-tert-butoxyphenoxy) phenyl group, 4- (2-sec-) Butoxyphenoxy) phenyl group, 3- (3-sec-butoxyphenoxy) phenyl group, 4- (4-sec-butoxyphenoxy) phenyl group, 2- (4-n-hexyloxyphenoxy) phenyl group, 3- (2 -N-heptafluoropropoxyphenoxy) phenyl group, 4- (3-n-heptafluo) Phenoxy-substituted phenyl groups such as lopropoxyphenoxy) phenyl group, 2- (4-n-heptafluoropropoxyphenoxy) phenyl group (1 to 5, preferably 1 to 3 halogen-substituted or not substituted on the phenyl ring) And C.sub.1-6 alkoxy groups may be substituted).

  Phenoxy group [on the phenyl ring, a halogen-substituted or unsubstituted C1-6 alkoxy group and a phenoxy-substituted phenyl group (on the phenyl ring, at least one halogen-substituted or unsubstituted C1-6 alkoxy group is substituted; As the group consisting of at least one group selected from the group consisting of (optionally substituted)], for example, phenoxy group, 2-methoxyphenoxy group, 3-methoxyphenoxy group, 4-methoxyphenoxy group , 4-isopropoxyphenoxy group, 4-n-butoxyphenoxy group, 2,4-dimethoxyphenoxy group, 2,3-dimethoxyphenoxy group, 2,3,4,5,6-pentamethoxyphenoxy group, 3,5 -Dimethoxyphenoxy group, 2,5-dimethoxyphenoxy group, 2,4,6-trimethoxyphenoxy group 3, -Di (trifluoromethoxy) phenoxy group, 4-methoxy-3-trifluoromethoxyphenoxy group, 2,6-dimethoxyphenoxy group, 2-trifluoromethoxyphenoxy group, 3-trifluoromethoxyphenoxy group, 4-trifluoro Methoxyphenoxy group, 2,3-di (trifluoromethoxy) phenoxy group, 2,4-di (trifluoromethoxy) phenoxy group, 2-pentafluoroethoxyphenoxy group, 3-pentafluoroethoxyphenoxy group, 4-pentafluoro Ethoxyphenoxy, 2-isopropoxyphenoxy, 3-isopropoxyphenoxy, 4-isopropoxyphenoxy, 2-tert-butoxyphenoxy, 3-tert-butoxyphenoxy, 4-tert-butoxyphenoxy, 2 - ec-butoxyphenoxy group, 3-sec-butoxyphenoxy group, 4-sec-butoxyphenoxy group, 4-n-hexyloxyphenoxy group, 2-n-heptafluoropropoxyphenoxy group, 3-n-heptafluoropropoxyphenoxy group , 4-n-heptafluoropropoxyphenoxy group, 2- (2-phenoxyphenyl) phenoxy group, 2,3-di (2-phenoxyphenyl) phenoxy group, 2,3-di (2-phenoxyphenyl) -4- 4 Methoxyphenoxy group, 2,4-dimethoxy-3- (3-phenoxyphenyl) phenoxy group, 3- (2,3-diphenoxyphenyl) phenoxy group, 4- (2,4,6-triphenoxyphenyl) phenoxy group , 2- [3- (2-methoxyphenoxy) phenyl] phenoxy group, 3- [4 -(3-methoxyphenoxy) phenyl] phenoxy group, 4- [2- (4-methoxyphenoxy) phenyl] phenoxy group, 2- [3- (4-isopropoxyphenoxy) phenyl] phenoxy group, 3- [4- (4-n-butoxyphenoxy) phenyl] phenoxy group, 4- [2- (2,4-dimethoxyphenoxy) phenyl] phenoxy group, 2- [3- (2,3-dimethoxyphenoxy) phenyl] phenoxy group, 3 -[4- (2,3,4,5,6-pentamethoxyphenoxy) phenyl] phenoxy group, 4- [2- (3,5-dimethoxyphenoxy) phenyl] phenoxy group, 2- [3- (2, 5-dimethoxyphenoxy) phenyl] phenoxy group, 3- [4- (2,4,6-trimethoxyphenoxy) phenyl] phenoxy group, 4- { -[3,5-di (trifluoromethoxy) phenoxy] phenyl} phenoxy group, 2- [3- (4-methoxy-3-trifluoromethoxyphenoxy) phenyl] phenoxy group, 3- [4- (2, 6) -Dimethoxyphenoxy) phenyl] phenoxy group, 4- [2- (2-trifluoromethoxyphenoxy) phenyl] phenoxy group, 2- [3- (3-trifluoromethoxyphenoxy) phenyl] phenoxy group, 3- [4-] (4-Trifluoromethoxyphenoxy) phenyl] phenoxy group, 4- {2- [2,3-di (trifluoromethoxy) phenoxy] phenyl} phenoxy group, 2- {3- [2,4-di (trifluoro) Methoxy) phenoxy] phenyl} phenoxy group, 3- [4- (2-pentafluoroethoxyphenoxy) phenyl Phenoxy group, 4- [2- (3-pentafluoroethoxyphenoxy) phenyl] phenoxy group, 2- [3- (4-pentafluoroethoxyphenoxy) phenyl] phenoxy group, 3- [4- (2-isopropoxyphenoxy] ) Phenyl] phenoxy group, 4- [2- (3-isopropoxy phenoxy) phenyl] phenoxy group, 2- [3- (4- isopropoxy phenoxy) phenyl] phenoxy group, 3- [2- (2- tert- Butoxyphenoxy) phenyl] phenoxy group, 4- [2- (3-tert-butoxyphenoxy) phenyl] phenoxy group, 2- [3- (4-tert-butoxyphenoxy) phenyl] phenoxy group, 3- [4- (4- (4-tert-butoxyphenoxy) phenyl] phenoxy group 2-sec-butoxyphenoxy) phenyl] phenoxy group, 2- [2- (3-sec-buto] Xyphenoxy) phenyl] phenoxy group, 2- [3- (4-sec-butoxyphenoxy) phenyl] phenoxy group, 4- [2- (4-n-hexyloxyphenoxy) phenyl] phenoxy group, 2- [3- (2-n-heptafluoropropoxyphenoxy) phenyl] phenoxy group, 3- [4- (3-n-heptafluoropropoxyphenoxy) phenyl] phenoxy group, 4- [2- (4-n-heptafluoropropoxyphenoxy) group Phenoxy groups such as phenyl] phenoxy group [in the phenyl ring, halogen substituted or unsubstituted C1-6 alkoxy group and phenoxy substituted phenyl group (in the phenyl ring, 1 to 5, preferably 1 to 3 Selected from the group consisting of halogen-substituted or unsubstituted C1-6 alkoxy groups which may be substituted) Groups 1-5 was, preferably can be mentioned may have 1 to 3 substituents.

  A homopiperazinyl group (in the homopiperazine ring, a C.sub.1-6 alkoxycarbonyl group, a phenyl C.sub.1-6 alkyl group [in the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted Or at least one of a group selected from the group consisting of C1-6 alkoxy groups, a phenyl group [in the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group, And at least one of a group selected from the group consisting of halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted], phenyl C1-6 alkoxycarbonyl group [a halogen atom on a phenyl ring, Halogen-substituted or unsubstituted C1-6 alkyl group and halogen-substituted or unsubstituted C1-6 alkyl group At least one of a group selected from the group consisting of xy groups may be substituted], phenylcarbamoyl group [wherein on a phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted Or at least one group selected from the group consisting of unsubstituted C.sub.1-6 alkoxy groups may be substituted, phenyl C.sub.2-6 alkenyl group [on the phenyl ring, a halogen atom, halogen substituted or not, or At least one of a group selected from the group consisting of a substituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group may be substituted; and a benzoyl group [on the phenyl ring, a halogen An atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group As at least one group selected from the group consisting of at least one group selected from the group may be substituted], for example, (1-, 2-,-, 3-, 4-, 5-, 6- or 7-) homopiperazinyl group, 4-tert-butoxycarbonyl-1-homopiperazinyl group, 4-ethoxycarbonyl-1-homopiperazinyl group, 4-methoxycarbonyl-1-homopiperazinyl group, 2,4-Dimethoxycarbonyl-1-homopiperazinyl group, 2,4,6-triethoxycarbonyl-1-homopiperazinyl group, 4- (4-trifluoromethoxybenzyl) -1-homopiperazinyl group, 4- (4-chlorobenzyl) ) -1-homopiperazinyl group, 4- (4-methoxybenzyl) -1-homopiperazinyl group, 4- (4-bromobenzyl) -1-homopiperazinyl, 4- (4-methylbenzyl) -1-homopiperazinyl, 4- (2,4-dichlorobenzyl) -1-homopiperazinyl, 4- (3,4-dimethoxybenzyl) -1-homopiperazinyl Group, 4- (2,4,6-trifluorobenzyl) -1-homopiperazinyl group, 4- (3,4-dimethylbenzyl) -1-homopiperazinyl group, 4- (2,4,6-trimethoxybenzyl) -1-homopiperazinyl group, 4- (2,4,6-trimethylbenzyl) -1-homopiperazinyl group, 4- (4-iodobenzyl) -1-homopiperazinyl group, 4- (4-trifluoromethylbenzyl) -1 -Homopiperazinyl group, 4- (3,4-dichlorobenzyl) -1-homopiperazinyl group, 4- [3- (4-trifluoromethylphenyl) group 2-propenyl] -1-homopiperazinyl group, 4- [3- (4-trifluoromethylphenyl) -2-propenyl] -1-homopiperazinyl group, 4- (4-trifluoromethylbenzoyl) -1-homopiperazinyl group, 4- [3- (4-chlorophenyl) -2-propenyl] -1-homopiperazinyl group, 4- [3- (4-methylphenyl) -2-propenyl] -1-homopiperazinyl group, 4- [3- (4 (4-) -Methoxyphenyl) -2-propenyl] -1-homopiperazinyl group, 4- [3- (3,4-dimethylphenyl) -2-propenyl] -1-homopiperazinyl group, 4- [3- (3,4-dimethoxy] group Phenyl) -2-propenyl] -1-homopiperazinyl group, 4- [3- (3,4,5-trimethylphenyl) -2-propenyl] -1-homo Perazinyl group, 4- [3- (3,4,5-trimethoxyphenyl) -2-propenyl] -1-homopiperazinyl group, 4- [3- (3,4-dichlorophenyl) -2-propenyl] -1- Homopiperazinyl group, 4- [3- (2,4,6-trifluorophenyl) -2-propenyl] -1-homopiperazinyl group, 4- [3- (4-iodophenyl) -2-propenyl] -1-homopiperazinyl Group, 4- [3- (3-bromophenyl) -2-propenyl] -1-homopiperazinyl group, 4- (4-fluorobenzyl) -1-homopiperazinyl group, 4- (4-methylbenzoyl) -1-homopiperazinyl group Group, 4- (4-methoxybenzoyl) -1-homopiperazinyl group, 4- (3,4-dimethylbenzoyl) -1-homopiperazinyl group, 4- (2,4-) Dimethoxybenzoyl) -1-homopiperazinyl group, 4- (3,4,5-trimethylbenzoyl) -1-homopiperazinyl group, 4- (2,4,6-trimethoxybenzoyl) -1-homopiperazinyl group, 4- (4 (4) -Chlorobenzoyl) -1-homopiperazinyl group, 4- (2,4,6-trifluorobenzoyl) -1-homopiperazinyl group, 4- (4-bromobenzoyl) -1-homopiperazinyl group, 4- (4-iodobenzoyl group) ) -1-homopiperazinyl, 4- (3,4-dichlorobenzoyl) -1-homopiperazinyl, 4- (4-fluorobenzoyl) -1-homopiperazinyl, 4-benzyl-3- (3-phenyl-2-) Propenyl) -1-homopiperazinyl group, 4-benzoyl-3,5-dibenzyl-1-homopiperazinyl group, 2 7-dibenzyl-4-phenyl-1-homopiperazinyl group; 4- (4-trifluoromethylphenyl) -1-homopiperazinyl group; 4- (4-trifluoromethoxyphenyl) -1-homopiperazinyl group; Chlorophenyl) -1-homopiperazinyl group, 4- (4-methoxyphenyl) -1-homopiperazinyl group, 4- (4-methylphenyl) -1-homopiperazinyl group, 4- (2,4-dimethoxyphenyl) -1-homopiperazinyl group Group, 4- (2,4-dimethylphenyl) -1-homopiperazinyl group, 4- (2,4,6-trimethoxyphenyl) -1-homopiperazinyl group, 4- (2,4,6-trimethylphenyl)- 1-homopiperazinyl group, 4- (3,4-dichlorophenyl) -1-homopiperazinyl group, 4- (2,4,6 Trifluorophenyl) -1-homopiperazinyl group, 4- (4-bromophenyl) -1-homopiperazinyl group, 4- (4-iodophenyl) -1-homopiperazinyl group, 4- (4-fluorophenyl) -1-homopiperazinyl group Group, 4- (4-trifluoromethoxybenzyloxycarbonyl) -1-homopiperazinyl group, 4- (4-chlorobenzyloxycarbonyl) -1-homopiperazinyl group, 4- (4-methoxybenzyloxycarbonyl) -1-homopiperazinyl group Group, 4- (4-bromobenzyloxycarbonyl) -1-homopiperazinyl group, 4- (4-methylbenzyloxycarbonyl) -1-homopiperazinyl group, 4- (2,4-dichlorobenzyloxycarbonyl) -1-homopiperazinyl Group, 4- (3,4-dimethoxybenzyl) Roxycarbonyl) -1-homopiperazinyl group, 4- (2,4,6-trifluorobenzyloxycarbonyl) -1-homopiperazinyl group, 4- (3,4-dimethylbenzyloxycarbonyl) -1-homopiperazinyl group, 4 -(2,4,6-trimethoxybenzyloxycarbonyl) -1-homopiperazinyl group, 4- (2,4,6-trimethylbenzyloxycarbonyl) -1-homopiperazinyl group, 4- (4-iodobenzyloxycarbonyl) -1-homopiperazinyl group, 4- (4-trifluoromethylbenzyloxycarbonyl) -1-homopiperazinyl group, 4- (3,4-dichlorobenzyloxycarbonyl) -1-homopiperazinyl group, 4- (4-trifluoromethoxy) group Phenylcarbamoyl) -1-homopiperazinyl group, 4 (4-chlorophenylcarbamoyl) -1-homopiperazinyl group, 4- (4-methoxyphenylcarbamoyl) -1-homopiperazinyl group, 4- (4-bromophenylcarbamoyl) -1-homopiperazinyl group, 4- (4-methylphenylcarbamoyl group ) 1-homopiperazinyl group, 4- (2,4-dichlorophenylcarbamoyl) -1-homopiperazinyl group, 4- (3,4-dimethoxyphenylcarbamoyl) -1-homopiperazinyl group, 4- (2,4,6-triyl group) Fluorophenylcarbamoyl) -1-homopiperazinyl group, 4- (3,4-dimethylphenylcarbamoyl) -1-homopiperazinyl group, 4- (2,4,6-trimethoxyphenylcarbamoyl) -1-homopiperazinyl group, 4- (4 2,4,6-trimethylphenyl carba Yl) -1-homopiperazinyl group, 4- (4-iodophenylcarbamoyl) -1-homopiperazinyl group, 4- (4-trifluoromethylphenylcarbamoyl) -1-homopiperazinyl group, 3,4-di (phenylcarbamoyl)- Homopiperazinyl groups such as 1-homopiperazinyl group, 4- [2- (4-trifluoromethylphenyl) ethyl] -1-homopiperazinyl group, 4- [3- (4-trifluoromethylphenyl) propyl] -1-homopiperazinyl group, etc. (C1-6 alkoxycarbonyl group on the homopiperazine ring, phenyl C1-6 alkyl group [halogen atom, halogen substituted or unsubstituted C1-6 alkyl group and halogen substituted or unsubstituted C1 on the phenyl ring 1 to 5 groups selected from the group consisting of Or a phenyl group [in the phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group] Group selected from the group consisting of 1 to 5 groups, preferably 1 to 3 groups, phenyl C1-6 alkoxycarbonyl group [on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted group 1 to 5, preferably 1 to 3 groups selected from the group consisting of a C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group may be substituted], phenylcarbamoyl group [phenyl On the ring, a group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group 1 to 5, preferably 1 to 3 selected groups may be substituted], phenyl C2-6 alkenyl group [unsubstituted or halogen atom, halogen substituted or unsubstituted C1-6 alkyl group and halogen substituted Or a group selected from unsubstituted C1-6 alkoxy groups is 1 to 2 and preferably 1 to 3 substituted phenyl groups, each having 1 to 2 carbon atoms and 2 to 6 carbon atoms, each having 1 to 2 double bonds It is a group comprised from the alkenyl group which it has. And phenyl group [1 to 5 groups selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group on the phenyl ring] , And preferably 1 to 3 groups may be substituted], and groups selected from the group consisting of 1 to 3 may be substituted).

  1,2,3,4-tetrahydroisoquinolyl group (on the 1,2,3,4-tetrahydroisoquinoline ring, at least one amino group [on the amino group a phenyl C At least one selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted on the ring And at least one group selected from the group consisting of C.sub.1-6 alkyl groups may be substituted), for example, as 1,2,3,4-tetrahydro (for example, 1-, 2-, 3-, 4-, 5-, 6-, 7- or 8-) isoquinolyl group, 4,6-diamino-1,2,3,4-tetrahydro-2-isoquinolyl group, 4, 6,7-triamino-1,2 3,4-tetrahydro-2-isoquinolyl group, 7- [N-methyl-N- (4-trifluoromethoxybenzyl) amino] -1,2,3,4-tetrahydro-2-isoquinolyl group, 6- (4 -Trifluoromethoxyphenoxy) -1,2,3,4-tetrahydro-2-isoquinolyl group, 7- [N-methyl-N- (4-trifluoromethylbenzyl) amino] -1,2,3,4- Tetrahydro-2-isoquinolyl group, 7- [N-methyl-N- (4-chlorobenzyl) amino] -1,2,3,4-tetrahydro-2-isoquinolyl group, 7- [N- (4-chlorobenzyl) ) Amino] -1,2,3,4-tetrahydro-2-isoquinolyl group, 7- {N-methyl-N- [2,4,6-tri (trifluoromethoxy) benzyl] amino} -1,2, 3, 4 Tetrahydro-2-isoquinolyl group, 7- {N-methyl-N- [2,4-di (trifluoromethyl) benzyl] amino} -1,2,3,4-tetrahydro-2-isoquinolyl group, 7- [7 1,2,3,4-Tetrahydroisoquinolyl groups such as N-methyl-N- (2,3-diiodobenzyl) amino] -1,2,3,4-tetrahydro-2-isoquinolyl group (1,1 On the 2,3,4-tetrahydroisoquinoliline ring there are 1 to 3 amino groups [on the amino group a phenyl C.sub.1-6 alkyl group (on the phenyl ring a halogen atom, halogen substituted or unsubstituted 1 to 5, preferably 1 to 3 groups selected from the group consisting of C1-6 alkyl groups of the above and halogen-substituted or unsubstituted C1-6 alkoxy groups, and C1-6 alkyl Selected from the group consisting of And the like may be substituted).

  An oxazolyl group (on the oxazole ring, a phenyl group [on the phenyl ring, selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group; C 1-6 alkyl group and piperidyl group [in the piperidine ring, at least one phenoxy group (on the phenyl ring, a halogen atom, halogen-substituted or not At least one of a group selected from the group consisting of a substituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group may be substituted or substituted) And the like] may be, for example, a (2-, 4- or 5-) oxazolyl group, 4- 4-chlorophenyl) -2-oxazolyl group, 4- (4-trifluoromethoxyphenyl) -2-oxazolyl group, 2- (4-trifluoromethylphenyl) -4-oxazolyl group, 4- (4-trifluoromethyl) Phenyl) -2-oxazolyl group, 2- (4-trifluoromethoxyphenyl) -4-oxazolyl group, 4- (3,4-dichlorophenyl) -2-oxazolyl group, 5- (4-bromophenyl) -2- Oxazolyl group, 4- (4-fluorophenyl) -2-oxazolyl group, 5- (4-iodophenyl) -2-oxazolyl group, 2- (2,4,6-trifluorophenyl) -4-oxazolyl group, 4- (4-methylphenyl) -2-oxazolyl group, 4- (3-methoxyphenyl) -2-oxazolyl group, 2- (3,4-dime) L-phenyl) -5-oxazolyl group, 4- (2,4-dimethoxyphenyl) -2-oxazolyl group, 4- (2,4,6-trimethylphenyl) -2-oxazolyl group, 4- (3,4,5 -Trimethoxyphenyl) -2-oxazolyl group, 4,5-diphenyl-2-oxazolyl group, 2,4-diphenyl-5-oxazolyl group, 4-methyl-5- [4- (4-trifluoromethoxyphenoxy) An oxazolyl group such as-(1-, 2- or 3-) piperidyl] -2-oxazolyl group (a phenyl group on a oxazole ring, a halogen atom on a phenyl ring, halogen substituted or unsubstituted C1 to C6; 1 to 5, preferably 1 to 3 groups selected from the group consisting of an alkyl group and a halogen substituted or unsubstituted C1 to 6 alkoxy group may be substituted], C1 to C6 6 alkyl group and piperidyl group [1 to 3 phenoxy groups on the piperidine ring (a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1 6 groups selected from the group consisting of alkoxy groups may be substituted by 1 to 5, preferably 1 to 3 groups] may be substituted by 1 to 2 groups selected from the group May be substituted).

  An isoindolinyl group (on the isoindoline ring, at least one of a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group is substituted. And the like, for example, (1-, 2-, 4- or 5-) isoindolinyl group, 4-chloro- (1-, 2-, 3-, 5-, 6- or 7-)- Isoindolinyl group, 4-trifluoromethyl- (1-, 2-, 3-, 5-, 6- or 7-)-isoindolinyl group, 4-trifluoromethoxy- (1-, 2-, 3-, 5- , 6- or 7-)-isoindolinyl group, 5-methyl- (1-, 2-, 3-, 4-, 6- or 7-)-isoindolinyl group, 4-methoxy- (1-, 2-, 3) -, 5-, 6- or 7-) Drylyl group, 3,4-Difluoro- (1-, 2-, 5-, 6- or 7-) isoindolinyl group, 4, 5, 6-trichloro (1-, 2-, 3- or 7-) isoindolinyl group 4,5-Dimethyl (1-, 2-, 3-, 6- or 7-) isoindolinyl group, 4, 5, 6-trimethyl (1-, 2-, 3- or 7-) isoindolinyl group, 4, 4, 5-dimethoxy (1-, 2-, 3-, 6- or 7-) isoindolinyl group, 4, 5, 6-trimethoxy (1-, 2-, 3- or 7-) isoindolinyl group, 1, 1-dimethyl An isoindolinyl group such as a -5-bromo- (2-, 3-, 4-, 6- or 7-) isoindolinyl group (on the isoindoline ring, a halogen atom, said halogen substituted or unsubstituted C1-6 alkyl as indicated above) Group and halogen substituted or not Groups selected from the group consisting of C1~6 alkoxy group conversion can be cited also may) have been 1-3 substituents.

  Piperazinyl group [in which at least one phenyl group (on the phenyl ring, a group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group on the phenyl ring is selected At least one of the selected groups may be substituted), for example, (1-, 2- or 3-) piperazinyl, 4-phenyl-1-piperazinyl Group, 2,4-diphenyl-1-piperazinyl group, 2,4,5-triphenyl-1-piperazinyl group, 4- (4-trifluoromethoxyphenyl) -1-piperazinyl group, 4- (4-trifluoro) Methylphenyl) -1-piperazinyl group, (4-chlorophenyl-1-piperazinyl) methyl group, 4- (2,4-dichlorophenyl) -1-pipe Dinyl group, 4- (2,4,6-trifluorophenyl) -1-piperazinyl group, 2,4-di (trifluoromethyl) phenyl-1-piperazinyl group, 2,4,6-tri (trifluoromethoxy) Piperazinyl groups such as phenyl-1-piperazinyl group [1 to 3 phenyl groups on the piperazine ring (on the phenyl ring, halogen atoms, halogen substituted or unsubstituted C1-6 alkyl groups and halogen substituted or 1 to 5 and preferably 1 to 3 groups selected from the group consisting of unsubstituted C1-6 alkoxy groups may be substituted].

  [Piperidyl group [on the piperidine ring (on the phenyl ring is selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group. As at least one kind of group selected from the group consisting of at least one kind of group may be substituted and phenyl C1-6 alkyl group may be substituted, for example, as the above-mentioned piperidyl group [piperidine ring Above, at least one phenoxy group (on the phenyl ring, a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group In which at least one of them may be substituted), in addition to 4-benzyl- (1-, 2- or 3 ) Piperidyl group, 3-benzyl- (1-, 2-, 4-, 5- or 6-) piperidyl group, 2-benzyl- (1-, 3-, 4-, 5- or 6-) piperidyl group, 2,4-dibenzyl- (1-, 3-, 5- or 6-) piperidyl group, 2, 3,4- tribenzyl- (1-, 5- or 6-) piperidyl group, 4-phenoxy-3-benzyl group -A piperidyl group such as a (1-, 2-, 5- or 6-) piperidyl group [a piperidine ring, a phenoxy group (a phenyl atom, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and A group selected from the group consisting of a halogen-substituted or unsubstituted C1-6 alkoxy group is selected from the group consisting of 1 to 5, preferably 1 to 3, and a phenyl C1-6 alkyl group; 1 to 3 substituted groups may be substituted ] Can be exemplified.

A thiazolyl group (on the thiazolyl ring, a phenoxy C1-6 alkyl group [on the phenyl ring, a group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group At least one of the selected groups may be substituted; phenyl group [in the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 At least one group selected from the group consisting of alkoxy groups may be substituted; phenyl C1-6 alkyl group [on the phenyl ring, a halogen atom, halogen substituted or unsubstituted C1-6 alkyl group and At least one of a group selected from the group consisting of halogen substituted or unsubstituted C1-6 alkoxy group And may be]; group ^{_{- (W 1) oNR 31 '}} R 32' [W 1 and o are as defined above .R ^{31 'and} R ^32' are the same or different, a hydrogen atom, Cl to 6 alkyl radical Phenyl group (in the phenyl ring, at least one of a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group is substituted. Or a phenyl C1-6 alkyl group (on the phenyl ring, selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group, and a halogen substituted or unsubstituted C1-6 alkoxy group At least one of the above-mentioned groups may be substituted)]; Piperazinyl [in the piperazine ring, at least one phenyl group (on the phenyl ring, a halogen atom, C At least one of a group selected from the group consisting of a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted) A piperidyl group [on a piperidine ring, a phenoxy group (on a phenyl ring, selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group; And at least one group selected from the group consisting of phenyl C1-6 alkyl group may be substituted] and phenoxy group [on the phenyl ring, From the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group As at least one kind of group selected from the group consisting of at least one kind of branched group may be substituted, for example, (2-, 4- or 5-) Thiazolyl group, 2-[(4-fluoromethoxyphenoxy) methyl] -4-thiazolyl group, 4-[(4-fluoromethoxyphenoxy) methyl] -2-thiazolyl group, 2-[(4-fluoromethylphenoxy) methyl ] 4-thiazolyl group, 2-[(4-chlorophenoxy) methyl] -4-thiazolyl group, 2-[(3-methoxyphenoxy) methyl] -4-thiazolyl group, 2-[(2-methylphenoxy) group] Methyl] -5-thiazolyl group, 2-[(2,4-dimethoxyphenoxy) methyl] -5-thiazolyl group, 2-[(3,4-dimethylphenoxy) methyl] -4-thiazole Group, 5-[(2,4,6-trimethoxyphenoxy) methyl-2-thiazolyl group, 2-[(3,4,5-trimethylphenoxy) methyl] -4-thiazolyl group, 2-[(2, 2, 6 4,6-Trifluorophenoxy) methyl] -4-thiazolyl group, 4-([3,4-dichlorophenoxy] methyl) -2-thiazolyl group, 2- [4-bromophenoxy] methyl] -4-thiazolyl group , 2-[(4-iodophenoxy) methyl] -4-thiazolyl group, 4-[(4-fluorophenoxy) methyl] -2-thiazolyl group, 2,5-diphenoxymethyl-4-thiazolyl group, 4, 5-diphenoxymethyl-2-thiazolyl group, 2- (4-fluorophenyl) -4-thiazolyl group, 4- (4-fluorophenyl) -2-thiazolyl group, 2- (4-chlorophenyl) ) 4-thiazolyl group, 4- (4-chlorophenyl) -2-thiazolyl group, 2- (4-trifluoromethylphenyl) -4-thiazolyl group, 2- (4-trifluoromethoxyphenyl) -4-thiazolyl Group, 4- (4-trifluoromethylphenyl) -2-thiazolyl group, 4- (4-trifluoromethoxyphenyl) -2-thiazolyl group, 2- (3,4-dichlorophenyl) -4-thiazolyl group, 4 -(3,4-dichlorophenyl) -2-thiazolyl group, 4- (2,4,6-trifluorophenyl) -2-thiazolyl group, 5- (4-bromophenyl) -2-thiazolyl group, 5- (4- 4-fluorophenyl) -4-thiazolyl group, 2- (4-iodophenyl) -5-thiazolyl group, 2- (4-methylphenyl) -4-thiazolyl group, 2- (4-methylphenyl) -4-thiazolyl group Xyphenyl) -4-thiazolyl group, 2- (2,4-dimethylphenyl) -5-thiazolyl group, 4- (3,4-dimethoxyphenyl) -2-thiazolyl group, 4- (2,4,6-trimethyl group Phenyl) -5-thiazolyl group, 5- (3,4,5-trimethoxyphenyl) -4-thiazolyl group, 2,4-diphenyl-5-thiazolyl group, 4,5-diphenyl-2-thiazolyl group, 2 -Phenyl-5-phenoxymethyl-4-thiazolyl group, 2- (4-fluorobenzyl) -4-thiazolyl group, 2- (4-chlorobenzyl) -4-thiazolyl group, 2- (4-trifluoromethylbenzyl) ) -4-thiazolyl group, 2- (4-trifluoromethoxybenzyl) -4-thiazolyl group, 2- (3,4-dichlorobenzyl) -4-thiazolyl group, 4- (2,4 (2,4) 6-trifluorobenzyl) -2-thiazolyl group, 5- (4-bromobenzyl) -2-thiazolyl group, 5- (4-fluorobenzyl) -4-thiazolyl group, 2- (4-iodobenzyl) -5 -Thiazolyl group, 2- (4-methylbenzyl) -4-thiazolyl group, 2- (4-methoxybenzyl) -4-thiazolyl group, 2- (2,4-dimethylbenzyl) -5-thiazolyl group, 4- (3,4-Dimethoxybenzyl) -2-thiazolyl group, 4- (2,4,6-trimethylbenzyl) -5-thiazolyl group, 5- (3,4,5-trimethoxybenzyl) -4-thiazolyl group , 2,4-dibenzyl-5-thiazolyl, 4,5-dibenzyl-2-thiazolyl, 2-benzyl-5-phenoxymethyl-4-thiazolyl, 4- (4-chlorobenzyl) amino -2-thiazolyl group, 4- (4-trifluoromethoxybenzyl) amino-2-thiazolyl group, 4- (4-trifluoromethylbenzyl) amino-2-thiazolyl group, 4- [N-methyl-N- ( 4-chlorobenzyl) amino] -2-thiazolyl group, 4- [N-methyl-N- (4-trifluoromethoxybenzyl) amino] -2-thiazolyl group, 4- [N-methyl-N- (4-) Trifluoromethylbenzyl) amino] -2-thiazolyl group, 4- (4-chlorophenyl) amino-2-thiazolyl group, 4- (4-trifluoromethoxyphenyl) amino-2-thiazolyl group, 4- (4-trilyl) Fluoromethylphenyl) amino-2-thiazolyl group, 4- [N-methyl-N- (4-chlorophenyl) amino] -2-thiazolyl group, 4- [N-methyl-N (4-Trifluoromethoxyphenyl) amino] -2-thiazolyl group, 4- [N-methyl-N- (4-trifluoromethylphenyl) amino] -2-thiazolyl group, 4- (4-chlorobenzyl) amino Methyl-2-thiazolyl group, 4- (4-trifluoromethoxybenzyl) aminomethyl-2-thiazolyl group, 4- (4-trifluoromethylbenzyl) aminomethyl-2-thiazolyl group, 4- [N-methyl- N- (4-chlorobenzyl) aminomethyl] -2-thiazolyl group, 4- [N-methyl-N- (4-trifluoromethoxybenzyl) aminomethyl] -2-thiazolyl group, 4- [N-methyl- N- (4-Trifluoromethylbenzyl) aminomethyl] -2-thiazolyl group, 4- (4-chlorophenyl) aminomethyl-2-thiazolyl group 4- (4-trifluoromethoxyphenyl) aminomethyl-2-thiazolyl group, 4- (4-trifluoromethylphenyl) aminomethyl-2-thiazolyl group, 4- [N-methyl-N- (4-chlorophenyl) group Aminomethyl] -2-thiazolyl group, 4- [N-methyl-N- (4-trifluoromethoxyphenyl) aminomethyl] -2-thiazolyl group, 4- [N-methyl-N- (4-trifluoromethyl) Phenyl) aminomethyl] -2-thiazolyl group, 4- (4-bromobenzyl) amino-2-thiazolyl group, 4- (4-methoxybenzyl) amino-2-thiazolyl group, 4- (4-methylbenzyl) amino -2-thiazolyl group, 4- [N-methyl-N- (3,4-dichlorobenzyl) amino] -2-thiazolyl group, 4- [N-methyl-N- (2 ,, 4-dimethoxybenzyl) amino] -2-thiazolyl group, 4- [N-methyl-N- (3,4-dimethylbenzyl) amino] -2-thiazolyl group, 4- (4-bromophenyl) amino-2- Thiazolyl group, 4- (4-methoxyphenyl) amino-2-thiazolyl group, 4- (4-methylphenyl) amino-2-thiazolyl group, 4- [N-methyl-N- (3,4-dichlorophenyl) amino ] 2-thiazolyl group, 4- [N-methyl-N- (3,4-dimethoxyphenyl) amino] -2-thiazolyl group, 4- [N-methyl-N- (2,4-dimethylphenyl) amino 4- (4-bromobenzyl) aminomethyl-2-thiazolyl group, 4- (4-methoxybenzyl) aminomethyl-2-thiazolyl group, 4- (4-methylbenzyl group) Aminomethyl-2-thiazolyl group, 4- [N-methyl-N- (3,4-dichlorobenzyl) aminomethyl] -2-thiazolyl group, 4- [N-methyl-N- (4-methoxybenzyl) amino Methyl] -2-thiazolyl group, 4- [N-methyl-N- (3,4-dimethylbenzyl) aminomethyl] -2-thiazolyl group, 4- (4-bromophenyl) aminomethyl-2-thiazolyl group, 4- (4-methoxyphenyl) aminomethyl-2-thiazolyl group, 4- (4-methylphenyl) aminomethyl-2-thiazolyl group, 4- [N-methyl-N- (3,4-dichlorophenyl) aminomethyl ] -2-thiazolyl group, 4- [N-methyl-N- (2,4-dimethoxyphenyl) aminomethyl] -2-thiazolyl group, 4- [N-methyl-N- (3,4-dimethyl) Phenyl) aminomethyl] -2-thiazolyl group, 4- (4-fluorobenzyl) amino-2-thiazolyl group, 4- (2,4,6-trimethoxybenzyl) amino-2-thiazolyl group, 4- (3 4,5-trimethylbenzyl) amino-2-thiazolyl group, 4- [N-methyl-N- (4-iodobenzyl) amino] -2-thiazolyl group, 4- [N-methyl-N- (2, 4,6-Trifluorobenzyl) amino] -2-thiazolyl group, 4- [N-methyl-N- (4-iodobenzyl) amino] -2-thiazolyl group, 4- (4-fluorophenyl) amino-2 -Thiazolyl group, 4- (2,4,6-trimethoxyphenyl) amino-2-thiazolyl group, 4- (3,4,5-trimethylphenyl) amino-2-thiazolyl group, 4- [N-methyl- N-( 4-iodophenyl) amino] -2-thiazolyl group, 4- [N-methyl-N- (2,4,6-trifluorophenyl) amino] -2-thiazolyl group, 4- (4-fluorobenzyl) amino Methyl-2-thiazolyl group, 4- (3,4,6-trimethoxybenzyl) aminomethyl-2-thiazolyl group, 4- (2,4,6-trimethylbenzyl) aminomethyl-2-thiazolyl group, 4- [N-Methyl-N- (4-iodobenzyl) aminomethyl] -2-thiazolyl group, 4- [N-methyl-N- (2,4,6-trifluorobenzyl) aminomethyl] -2-thiazolyl group 4- (4-Fluorophenyl) aminomethyl-2-thiazolyl group, 4- (2,4,6-trimethoxyphenyl) aminomethyl-2-thiazolyl group, 4- (3,4,5-trimethyl group Phenyl) aminomethyl-2-thiazolyl group, 4- [N-methyl-N- (4-iodophenyl) aminomethyl] -2-thiazolyl group, 4- [N-methyl-N- (2,4,6-) Trifluorophenyl


) Aminomethyl] -2-thiazolyl group, 4- [N-methyl-N- (4-trifluoromethylphenyl) aminomethyl] -2-thiazolyl group, 4- (4-trifluoromethoxyphenoxy) -2-thiazolyl Group, 4- (4-trifluoromethylphenoxy) -2-thiazolyl group, 4- (4-chlorophenoxy) -2-thiazolyl group, 4- (3,4-dichlorophenoxy) -2-thiazolyl group, 4- (4-methoxyphenoxy) -2-thiazolyl group, 4- (4-methylphenoxy) -2-thiazolyl group, 4- (3,4-dimethoxyphenoxy) -2-thiazolyl group, 5- (2,4-dimethyl) group Phenoxy) -4-thiazolyl group, 4- (2,4,6-trimethoxyphenoxy) -5-thiazolyl group, 4- (3,4,5-trimethylphenoxy) -2- Azolyl group, 4- (4-fluorophenoxy) -2-thiazolyl group, 2- (4-bromophenoxy) -5-thiazolyl group, 2- (4-iodophenoxy) -4-thiazolyl group, 5- (2, 4,6-Trifluorophenoxy) -2-thiazolyl group, 4- [4- (4-trifluoromethylphenyl) -1-piperazinyl] -2-thiazolyl group, 4- [4- (4-trifluoromethoxyphenyl) ) -1-Piperazinyl] -2-thiazolyl group, 4- [4- (4-chlorophenyl) -1-piperazinyl] -2-thiazolyl group, 4- [4- (4-trifluoromethylphenoxy) -1-piperidyl ] 2-thiazolyl group, 4- [4- (4-trifluoromethoxyphenoxy) -1-piperidyl] -2-thiazolyl group, 4- [4- (4-chlorophenoxy] -1-piperidyl] -2-thiazolyl group, 5- [3,4-diphenyl-1-piperazinyl] -2-thiazolyl group, 2- [3,4,5-triphenyl-1-piperazinyl] -4-thiazolyl Group, 5- [3,4,5-triphenoxy-1-piperidyl] -4-thiazolyl group, 4- [3,4-diphenoxy-1-piperidyl] -5-thiazolyl group, 4- [4- (4 (4) -Trifluoromethoxyphenyl) -1-piperazinyl] -5-phenoxy-2-thiazolyl group, 4- [4- (4-trifluoromethoxyphenoxy) -1-piperidyl] -5-phenoxy-2-thiazolyl group, 4 Thialia such as -phenyl-2-thiazolyl group, 2-phenyl-4-thiazolyl group, 2- [4-benzyl- (1-, 2- or 3-) piperidyl]-(4- or 5-) thiazolyl group, etc. Zoryl group (on thiazole ring, phenoxy C.sub.1-6 alkyl group [on phenyl ring, halogen atom, halogen substituted or unsubstituted C.sub.1-6 alkyl group and halogen substituted or unsubstituted C.sub.1-6 alkoxy group. [1 to 5 and preferably 1 to 3 selected groups may be substituted] phenyl group [on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted Or a group selected from the group consisting of unsubstituted C1-6 alkoxy groups may be substituted with 1 to 5, preferably 1 to 3 groups; phenyl C1-6 alkyl group [on the phenyl ring, A group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group is Pieces, preferably may be in 1-3 substituents]; group ^{_{- (W 1) oNR 31 '}} R 32' [W 1 and o are as defined above. R ^{31 ′} and R ^{32 ′} are the same or different and each is a hydrogen atom, a C1-6 alkyl group, a phenyl group (on a phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or not One to five, preferably one to three, of the groups selected from the group consisting of substituted C1-6 alkoxy groups may be substituted, or a phenyl C1-6 alkyl group (a halogen atom on the phenyl ring) Or 1-5, preferably 1 to 3 groups selected from the group consisting of halogen-substituted or unsubstituted C1-6 alkyl groups and halogen-substituted or unsubstituted C1-6 alkoxy groups) Indicates Piperazinyl group [in the piperazine ring, at least 1 to 3 phenyl groups (on the phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 group; A group selected from the group consisting of an alkoxy group may be substituted by 1 to 5, preferably 1 to 3)]; piperidyl group [a phenoxy group on a piperidine ring On the phenyl ring, 1 to 5 groups, preferably 1 to 3 groups selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group are preferable. And one to three groups selected from the group consisting of phenyl C1-6 alkyl groups may be substituted) and phenoxy groups [on the phenyl ring, 1 to 5, preferably 1 to 3 groups selected from the group consisting of a gen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group And one or two groups selected from the group consisting of (1) may be substituted).

  An oxazolyl C.sub.1-6 alkyl group (on the oxazole ring at least one phenyl group [on a phenyl ring a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6. Examples of the group in which at least one group selected from the group consisting of an alkoxy group may be substituted] may be, for example, a [(2-, 4- or 5-) oxazolyl] methyl group 1-[(2-, 4- or 5-) oxazolyl] ethyl group, 2-[(2-, 4- or 5-) oxazolyl] ethyl group, 3-[(2-, 4- or 5-) group Oxazolyl] propyl group, 2-[(2-, 4- or 5-) oxazolyl] propyl group, 4-[(2-, 4- or 5-) oxazolyl] butyl group, 5-[(2-, 4-] Or 5-) oxazolyl] pliers Group, 4-[(2-, 4- or 5-) oxazolyl] pentyl group, 6-[(2-, 4- or 5-) oxazolyl] hexyl group, 2-methyl-3-[(2-, 4) -Or 5-) oxazolyl] propyl group, 1,1-dimethyl-2-[(2-, 4- or 5-) oxazolyl] ethyl group, 4- (4-trifluoromethoxyphenyl)-(2- or 5) -) Oxazolyl methyl group, 4- (4-chlorophenyl)-(2- or 5-) oxazolyl methyl group, 4- (4-trifluoromethylphenyl)-(2- or 5-) oxazolyl Methyl group, 4- (4-methylphenyl)-(2- or 5-) oxazolyl methyl group, 4- (4-methoxyphenyl)-(2- or 5-) oxazolyl methyl group, 4- (4- 2,4-Dichlorophenyl)-(2- or 5-) oxazo Methyl group, 4- (2,4,6-trifluorophenyl)-(2- or 5-) oxazolylmethyl group, 2- (3,4-dimethylphenyl)-(4- or 5-) oxazolate Methyl group, 5- (3,4,6-trimethylphenyl)-(2- or 4-) oxazolyl methyl group, 2- (3,4-dimethoxyphenyl)-(4- or 5-) oxazolate Methyl group, 4- (2,4,6-trimethoxyphenyl)-(2- or 5-) oxazolylmethyl group, 4- (3-chloro-4-trifluoromethoxyphenyl)-(2- or 5-) Oxazolylmethyl group, 2,4-diphenyl-5-oxazolylmethyl group, 4,5-diphenyl-2-oxazolylmethyl group, 2,5-diphenyl-5-oxazolylmethyl group And alkyl moieties such as C1 to C6 straight or branched Branched alkyl group oxazolyl C1-6 alkyl group [1 to 2 phenyl groups on the oxazole ring (a halogen atom, a halogen substituted or unsubstituted C1 to 6 alkyl group on the phenyl ring and a halogen 1 to 5, preferably 1 to 3 groups selected from the group consisting of substituted or unsubstituted C1-6 alkoxy groups may be substituted). .

  An isoxazolyl group (on the isoxazoline ring at least one phenyl group [on the phenyl ring a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group As at least one kind of group selected from the group consisting of) may be substituted), for example, (3-, 4- or 5-) isoxazolyl group, 3-phenyl- ( 4- or 5-) isoxazolyl group, 4-phenyl- (3- or 5-) isoxazolyl group, 5-phenyl- (3- or 4-) isoxazolyl group, 3,4-diphenyl-5- isoxazolyl group, 3, 5-diphenyl-4-isoxazolyl group, 4,5-diphenyl-3-isoxazolyl group, 3- (4-trifluorophenyl)-(4- or- -) Isoxazolyl group, 4- (4-chlorophenyl)-(3- or 5-) isoxazolyl group, 3- (4-trifluoromethylphenyl)-(4- or 5-) isoxazolyl group, 4- (4-methyl) Phenyl)-(3- or 5-) isoxazolyl group, 3- (4-methoxyphenyl)-(4- or 5-) isoxazolyl group, 4- (2,4-dichlorophenyl)-(3- or 5-) isoxazolyl Group, 3- (2,4,6-trifluorophenyl)-(4- or 5-) isoxazolyl group, 3- (3,4-diphenylmethyl)-(4- or 5-) isoxazolyl group, 5- ( 3,4,6-trimethylphenyl)-(3- or 4-) isoxazolyl group, 3- (3,4-dimethoxyphenyl)-(4- or 5-) isoxazolyl group, 4- Isoxazolyl groups such as 2,4,6-trimethoxyphenyl)-(3- or 5-) isoxazolyl group, 3- (3-chloro-4-trifluoromethoxyphenyl)-(4- or 5-) isoxazolyl group [ On the isoxazoline ring, one or two phenyl groups (on the phenyl ring, a group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group Groups selected from 1 to 5 and preferably 1 to 3 may be substituted).

  Examples of the benzoxazolyl group (wherein at least one halogen atom may be substituted on the benzoxazole ring) include, for example, (2-, 4-, 5-, 6- or 7-) benzooxa Zoryl group, 5-chloro- (2-, 4-, 6- or 7-) benzoxazolyl group, 6-chloro- (2-, 4-, 5- or 7-) benzoxazolyl group, 5-fluoro- (2-, 4-, 6- or 7-) benzoxazolyl group, 6-bromo- (2-, 4-, 5- or 7-) benzoxazolyl group, 5-iodo- (2-, 4-, 6- or 7-) benzoxazolyl group, 5,6-dichloro- (2-, 4- or 7-) benzoxazolyl group, 4,5,6-trifluoro- (2- or 7-) benzoxazolyl group, 5-fluoro-6-chloro- (2-, 4- or 7-) benzo (On the benzoxazole ring may be 1 to 3 halogen atoms are substituted) benzoxazolyl group such Kisazoriru group can be exemplified.

  A benzimidazolyl group [on a benzimidazole ring, a halogen atom and a phenyl C.sub.1-6 alkyl group (on a phenyl ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6. As at least one group selected from the group consisting of an alkoxy group, at least one group selected from the group consisting of an alkoxy group may be substituted], for example, (2-, 4-, 5-, 6- or 7-) benzoimidazolyl group, 1- (4-trifluoromethoxybenzyl) -5, 6-dichloro- (2-, 4- or 7-) benzoimidazolyl group, 5-chloro- ( 1-, 2-, 4-, 6- or 7-) benzoimidazolyl group, 6-chloro- (1-, 2-, 4-, 5- or 7-) benzimidazolyl group, 5-fluoro- ( -, 2-, 4-, 6- or 7-) benzoimidazolyl group, 6-bromo- (1-, 2-, 4-, 5- or 7-) benzimidazolyl group, 5-iodo- (1-, 2-) , 4-, 6- or 7-) benzoimidazolyl group, 5, 6-dichloro- (1-, 2-, 4- or 7-) benzoimidazolyl group, 4, 5, 6- trifluoro- (1-, 2-) Or 7-) benzoimidazolyl group, 5-fluoro-6-chloro- (1-, 2-, 4- or 7-) benzoimidazolyl group, 1-benzyl- (2-, 4-, 5-, 6- or 7-) ) Benzimidazolyl group, 1- (4-trifluoromethylbenzyl)-(2-, 4-, 5-, 6- or 7-) benzimidazolyl group, 1- (4-chlorobenzyl)-(2-, 4-, 4-) 5-, 6- or 7-) benzoimidazolyl group, 1- (3-methyl) 1) (2-, 4-, 5-, 6- or 7-) benzoimidazolyl group, 1- (2-methoxybenzyl)-(2-, 4-, 5-, 6- or 7-) benzimidazolyl group, 1- (3,4-dimethylbenzyl)-(2-, 4-, 5-, 6- or 7-) benzoimidazolyl group, 1- (2,4,6-trimethylbenzyl)-(2-, 4-, 6- 5-, 6- or 7-) benzoimidazolyl group, 1- (3,4-dimethoxybenzyl)-(2-, 4-, 5-, 6- or 7-) benzoimidazolyl group, 1- (2, 4, 5) -Trimethoxybenzyl)-(2-, 4-, 5-, 6- or 7-) benzoimidazolyl group, 1- (3,4-dichlorobenzyl)-(2-, 4-, 5-, 6- or 7) -) Benzimidazolyl group, 1- (2,4,6-trifluorobenzyl)-( 2-, 4-, 5-, 6- or 7-) benzoimidazolyl group, 1- (3-chloro-4-trifluoromethylbenzyl)-(2-, 4-, 5-, 6- or 7-) benzimidazolyl Groups such as benzimidazolyl group such as 1, 5, 4-dibenzyl- (2-, 4-, 6- or 7-) benzimidazolyl group, 1, 5, 6-tribenzyl- (2-, 4- or 7-) benzimidazolyl group etc. [A halogen atom and a phenyl C1-6 alkyl group on a benzimidazole ring (a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group on a phenyl ring Groups selected from the group consisting of 1 to 5 groups, and preferably 1 to 3 groups may be substituted).

  An imidazolyl group (on an imidazole ring, at least one phenyl group [on a phenyl ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group Examples of the group in which at least one group selected from the group may be substituted] are, for example, 2-phenyl- (4- or 5-) imidazolyl group, 4-phenyl- (2- or 5-) imidazolyl group, 2,4-diphenyl-5-imidazolyl group, 2,4-diphenyl-5-imidazolyl group, 4,5-diphenyl-2-imidazolyl group, 2- (4-trifluoro) Methoxyphenyl)-(4- or 5-) imidazolyl group, 2- (4-trifluorophenyl)-(4- or 5-) imidazolyl group, 4- (4-chloropheny) Yl)-(2- or 5-) imidazolyl group, 4- (4-trifluoromethylphenyl)-(2- or 5-) imidazolyl group, 4- (4-methylphenyl) -2-imidazolyl group, 2- (4-methoxyphenyl)-(4- or 5-) imidazolyl group, 4- (2,4-dichlorophenyl)-(2- or 5-) imidazolyl group, 2- (2,4,6-trifluorophenyl) -(4- or 5-) imidazolyl group, 2- (3,4-diphenylmethyl)-(4- or 5-) imidazolyl group, 5- (3,4,6-trimethylphenyl)-(2- or 4) -) Imidazolyl, 2- (3,4-dimethoxyphenyl)-(4- or 5-) imidazolyl, 4- (2,4,6-trimethoxyphenyl)-(2- or 5-) imidazolyl, 5- (3-chloro-4-to An imidazolyl group such as fluoromethoxyphenyl)-(2- or 4-) imidazolyl group (one or two phenyl groups on the imidazole ring [a halogen atom, halogen-substituted or unsubstituted C1 1 to 5, preferably 1 to 3 groups selected from the group consisting of 6 alkyl groups and halogen-substituted or unsubstituted C1-6 alkoxy groups] may be substituted Can be illustrated.

  Phenylsulfinyl group (in which at least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group is substituted on the phenyl ring And the like, for example, an unsubstituted phenylsulfinyl group and a halogen atom as defined above, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group Phenylsulfinyl group having 1 to 5, preferably 1 to 3 substituents selected from the group consisting of phenylsulfinyl group, 2-fluorophenylsulfinyl group, 3-fluorophenylsulfinyl group, 4-fluoro Phenylsulfinyl group, 2-chlorophenylsulfinyl group, 3-qu Rophenylsulfinyl group, 4-chlorophenylsulfinyl group, 2-bromophenylsulfinyl group, 3-bromophenylsulfinyl group, 4-bromophenylsulfinyl group, 2-iodophenylsulfinyl group, 3-iodophenylsulfinyl group, 4-iodophenyl Sulfinyl group, 2,3-difluorophenylsulfinyl group, 3,4-difluorophenylsulfinyl group, 3,5-difluorophenylsulfinyl group, 2,4-difluorophenylsulfinyl group, 2,6-difluorophenylsulfinyl group, 2, 3-dichlorophenylsulfinyl group, 3,4-dichlorophenylsulfinyl group, 3,5-dichlorophenylsulfinyl group, 2,4-dichlorophenylsulfinyl group, 2,6-dichlorophenylsulfone Group, 3,4,5-trifluorophenylsulfinyl group, 3,4,5-trichlorophenylsulfinyl group, 2,4,6-trifluorophenylsulfinyl group, 2,4,6-trichlorophenylsulfinyl group, 2 -Fluoro-4-bromophenylsulfinyl group, 4-chloro-3-fluorophenylsulfinyl group, 2,3,4-trichlorophenylsulfinyl group, 2,3,4,5,6-pentafluorophenylsulfinyl group, 2, 4,6-Trimethylphenylsulfinyl, 4-n-butylphenylsulfinyl, 2,4-dimethylphenylsulfinyl, 2,3-dimethylphenylsulfinyl, 2,6-dimethylphenylsulfinyl, 3,5-dimethyl Phenylsulfinyl group, 2,5-dimethylphenyls Ruffinyl group, 3,5-ditrifluoromethylphenylsulfinyl group, 4-n-butoxyphenylsulfinyl group, 2,4-dimethoxyphenylsulfinyl group, 2,3-dimethoxyphenylsulfinyl group, 2,6-dimethoxyphenylsulfinyl group, 3,5-Dimethoxyphenylsulfinyl group, 2,5-dimethoxyphenylsulfinyl group, 2,4,6-trimethoxyphenylsulfinyl group, 3,5-ditrifluoromethoxyphenylsulfinyl group, 3-chloro-4-methoxyphenylsulfinyl group Group, 2-chloro-4-trifluoromethoxyphenylsulfinyl group, 3-methyl-4-fluorophenylsulfinyl group, 4-bromo-3-trifluoromethylphenylsulfinyl group, 2-methylphenylsulfinyl group, -Methylphenylsulfinyl group, 4-methylphenylsulfinyl group, 2-methyl-3-chlorophenylsulfinyl group, 3-methyl-4-chlorophenylsulfinyl group, 2-chloro-4-methylphenylsulfinyl group, 2-methyl-3- Fluorophenylsulfinyl group, 2-trifluoromethylphenylsulfinyl group, 3-trifluoromethylphenylsulfinyl group, 4-trifluoromethylphenylsulfinyl group, 2-pentafluoroethylphenylsulfinyl group, 3-pentafluoroethylphenylsulfinyl group, 4-pentafluoroethylphenylsulfinyl group, 2-isopropylphenylsulfinyl group, 3-isopropylphenylsulfinyl group, 4-isopropylphenylsulfinyl group, 2-ter -Butylphenylsulfinyl group, 3-tert-butylphenylsulfinyl group, 4-tert-butylphenylsulfinyl group, 2-sec-butylphenylsulfinyl group, 3-sec-butylphenylsulfinyl group, 4-sec-butylphenylsulfinyl group , 2-n-heptafluoropropylphenylsulfinyl group, 3-n-heptafluoropropylphenylsulfinyl group, 4-n-heptafluoropropylphenylsulfinyl group, 4-n-pentylphenylsulfinyl group, 4-n-hexylphenylsulfinyl group Group, 2-methoxyphenylsulfinyl group, 3-methoxyphenylsulfinyl group, 4-methoxyphenylsulfinyl group, 3-chloro-2-methoxyphenylsulfinyl group, 2-fluoro-3-methoxy Xyphenylsulfinyl group, 2-fluoro-4-methoxyphenylsulfinyl group, 2,3,4-trifluorophenylsulfinyl group, 2-trifluoromethoxyphenylsulfinyl group, 3-trifluoromethoxyphenylsulfinyl group, 4-trifluoro Methoxyphenylsulfinyl group, 3-fluoro-2-trifluoromethoxyphenylsulfinyl group, 2-fluoro-3-trifluoromethoxyphenylsulfinyl group, 3-fluoro-4-trifluoromethoxyphenylsulfinyl group, 3-chloro-2- Trifluoromethoxyphenylsulfinyl group, 2-chloro-3-trifluoromethoxyphenylsulfinyl group, 3-chloro-4-trifluoromethoxyphenylsulfinyl group, 2-pentafluoroethoxyphenyl Rusulfinyl group, 3-pentafluoroethoxyphenylsulfinyl group, 4-pentafluoroethoxyphenylsulfinyl group, 3-chloro-2-pentafluoroethoxyphenylsulfinyl group, 2-chloro-3-pentafluoroethoxyphenylsulfinyl group, 3- Chloro-4-pentafluoroethoxyphenylsulfinyl group, 2-isopropoxyphenylsulfinyl group, 3-isopropoxyphenylsulfinyl group, 4-isopropoxyphenylsulfinyl group, 2-tert-butoxyphenylsulfinyl group, 3-tert-butoxyphenyl Sulfinyl group, 4-tert-butoxyphenylsulfinyl group, 2-sec-butoxyphenylsulfinyl group, 3-sec-butoxyphenylsulfinyl group, 4-se 4-butoxyphenylsulfinyl group, 2-n-heptafluoropropoxyphenylsulfinyl group, 3-n-heptafluoropropoxyphenylsulfinyl group, 4-n-heptafluoropropoxyphenylsulfinyl group, 4-n-pentoxyphenylsulfinyl group, 4 And -n-hexyloxyphenylsulfinyl group etc. can be mentioned.

  As the imidazolyl group (on the imidazole ring, at least one of a group selected from the group consisting of a halogen atom and a nitro group may be substituted), for example (1-, 2-, 4- or 5-) ) Imidazolyl group, 2-chloro-4-nitro- (1- or 5-) imidazolyl group, 2-bromo- (1-, 4- or 5-) imidazolyl group, 4-fluoro- (1-, 2- or 2-) 5-) Imidazolyl group, 2,5-dichloro- (1- or 4-) imidazolyl group, 2,4,5-trichloro-1-imidazolyl group, 2-nitro- (1-, 4- or 5-) imidazolyl group Imidazolyl such as 4-nitro- (1-, 2- or 5-) imidazolyl, 2,5-dinitro- (1- or 4-) imidazolyl, 2,4,5-trinitro-1-imidazolyl Group (on the imidazole ring Groups selected from halogen atoms and nitro group consisting group can be exemplified a may) also be 1-3 substituents.

  A phenyl C1-6 alkyl group (a group selected from the group consisting of a benzofuryl group, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group on the phenyl ring At least one member of the above may be substituted) as the above-mentioned phenyl C.sub.1-6 alkyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted In addition to 4-[(2-, 3-, 4-, 5-, 6-, or 7], in addition to at least one of a group selected from the group consisting of -) Benzofuryl] benzyl group, 2-[(2-, 3-, 4-, 5-, 6- or 7-) benzofuryl] benzyl group, 3-[(2-, 3-, 4-, 5-, 5-, 6- or 7- Benzofuryl! Benzyl group, 2,4-di [(2-, 3-, 4-, 5-, 6- or 7-) benzofuryl] benzyl group, 2,4, 6-tri [(2-, 3-, 4-, 5-, 6- or 7-) benzofuryl] benzyl group, 2-trifluoromethyl-4- (2-, 3-, 4-, 5-, 6- or 7-) benzofuryl] benzyl group, 3 -Trifluoromethoxy-4- (2-, 3-, 4-, 5-, 6- or 7-) benzofuryl] benzyl group, 4-chloro-3- (2-, 3-, 4-, 5-, 5-, 6- or 7-) benzofuryl] phenyl C1-6 alkyl group in which the alkyl moiety such as benzyl group is a linear or branched alkyl group having 1 to 6 carbon atoms (a benzofuryl group on a phenyl ring, a halogen atom , Halogen substituted or unsubstituted C1-6 alkyl group and halogen substituted Can be exemplified the one to five groups selected from the group consisting of C1~6 alkoxy group unsubstituted, preferably it may be in 1-3 substituents).

  A furyl C1-6 alkyl group [in which at least one phenyl group (a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or Examples of a group in which at least one group selected from the group consisting of an alkoxy group may be substituted may be substituted with, for example, a (2- or 3-) furylmethyl group, 1-[( 2- or 3-) furyl] ethyl group, 2-[(2- or 3-) furyl] ethyl group, 3-[(2- or 3-) furyl] propyl group, 2-[(2- or 3-) ) Furyl] propyl, 4-[(2- or 3-) furyl] butyl, 5-[(2- or 3-) furyl] pentyl, 4-[(2- or 3-) furyl] pentyl , 6-[(2- or 3-) furyl] hexyl group, 1,1-dimethyl-2- [ 2- or 3-) furyl] ethyl group, 2-methyl-3-[(2- or 3-) furyl] propyl group, 2- (4-chlorophenyl)-(3-, 4- or 5-) furyl methyl Group, 2- (2-chloro-5-trifluoromethylphenyl)-(3-, 4- or 5-) furylmethyl group, 2- (4-trifluoromethoxyphenyl)-(3-, 4- or 5 -) Furylmethyl group, 2- (2,4-dichlorophenyl)-(3-, 4- or 5-) furylmethyl group, 2- (2,4,6-trifluorophenyl)-(3-, 4-) Or 5-) furyl methyl group, 2- (4-methylphenyl)-(3-, 4- or 5-) furyl methyl group, 2- (4-methoxyphenyl)-(3-, 4- or 5-) Furyl methyl group, 2- (2,4-dimethylphenyl)-(3-, 4- or 5-) furyl Methyl group, 2- (3,4-dimethoxyphenyl)-(3-, 4- or 5-) furylmethyl group, 2- (2,4,6-trimethylphenyl)-(3-, 4- or 5-) ) Furyl methyl group, 2- (3,4,5-trimethoxyphenyl)-(3-, 4- or 5-) furyl methyl group, 2,4-diphenyl- (3- or 5-) furyl methyl group, Furyl C1-6 alkyl group wherein the alkyl moiety such as a 2,4,5-triphenyl-3-furylmethyl group is a linear or branched alkyl group having 1 to 6 carbon atoms [1 on the furan ring Groups selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group on the phenyl ring Five, preferably one to three, may be substituted. ) Can be exemplified a] may be substituted.

  Pyridyl C.sub.1-6 alkyl group [on a pyridine ring, a furyl group and a phenyl group (on a phenyl ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy. Group may be substituted by at least one group selected from the group consisting of groups) may be substituted by at least one group selected from the group consisting of groups In addition to the 6 alkyl group, 3- (2- or 3-) furyl- (2-, 4-, 5- or 6-) pyridylmethyl group, 2- (4-trifluoromethoxyphenyl)-(3-, 4-, 5- or 6-) pyridylmethyl group, 2- (4-trifluoromethylphenyl)-(3-, 4-, 5- or 6-) pyridylmethyl group, 2- (4-methoxyphenyl)- (3- 4-, 5- or 6-) pyridylmethyl group, 2- (4-methylphenyl)-(3-, 4-, 5- or 6-) pyridylmethyl group, 2- (3-chloro-4-fluorophenyl) )-(3-, 4-, 5- or 6-) pyridylmethyl group, 2- (2,4-dimethoxyphenyl)-(3-, 4-, 5- or 6-) pyridylmethyl group, 2- (2-) 3,4,5-trimethoxyphenyl)-(3-, 4-, 5- or 6-) pyridylmethyl group, 2- (2,4-dimethylphenyl)-(3-, 4-, 5- or 6 -) Pyridylmethyl group, 2- (2,4,6-trimethylphenyl)-(3-, 4-, 5- or 6-) pyridylmethyl group, 2- (2,4,6-trichlorophenyl)-( 3-, 4-, 5- or 6-pyridylmethyl group, 2- (3-chloro-4-trifluoromethoxy) Phenyl)-(3-, 4-, 5- or 6-) pyridylmethyl, 2,4-di (2- or 3-) furyl- (5- or 6) pyridylmethyl, 2, 4, 6 -An alkyl moiety such as triphenyl- (3- or 5-) pyridylmethyl group or 2-furyl-5-phenyl- (3-, 4- or 6-) pyridylmethyl group is a straight chain having 1 to 6 carbon atoms or A branched alkyl group pyridyl C1-6 alkyl group [in which a furyl group and a phenyl group (a phenyl group, a benzofuryl group, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group on a phenyl ring And a group selected from the group consisting of 1 to 5, preferably 1 to 3 groups selected from the group consisting of halogen-substituted or unsubstituted C1-6 alkoxy groups; [3] may be substituted Ru.

  Examples of the benzothienyl C1-6 alkyl group (wherein at least one halogen atom may be substituted on the benzothiophene ring) include, for example, 2-benzothienylmethyl group, 1- (2-benzothienyl) ethyl Group, 2- (4-benzothienyl) ethyl group, 3- (5-benzothienyl) propyl group, 4- (6-benzothienyl) butyl group, 5- (7-benzothienyl) pentyl group, 6- (2) -Benzothienyl) hexyl group, 4-fluoro-2-benzothienylmethyl group, 5-fluoro-2-benzothienylmethyl group, 6-fluoro-2-benzothienylmethyl group, 7-fluoro-2-benzothienylmethyl group , 4-chloro-2-benzothienylmethyl group, 5-chloro-2-benzothienylmethyl group, 6-chloro-2-benzothienylmethyl group, -Chloro-2-benzothienylmethyl group, 4-bromo-2-benzothienylmethyl group, 5-bromo-2-benzothienylmethyl group, 6-bromo-2-benzothienylmethyl group, 7-bromo-2-benzo Thienylmethyl group, 4-iodo-2-benzothienylmethyl group, 5-iodo-2-benzothienylmethyl group, 6-iodo-2-benzothienylmethyl group, 7-iodo-2-benzothienylmethyl group, 4- Fluoro-3-benzothienylmethyl group, 5-fluoro-3-benzothienylmethyl group, 6-fluoro-3-benzothienylmethyl group, 7-fluoro-3-benzothienylmethyl group, 4-chloro-3-benzothienyl group Methyl group, 5-chloro-3-benzothienylmethyl group, 6-chloro-3-benzothienylmethyl group, 7-chloro-3-be Zothienylmethyl group, 4-bromo-3-benzothienylmethyl group, 5-bromo-3-benzothienylmethyl group, 6-bromo-3-benzothienylmethyl group, 7-bromo-3-benzothienylmethyl group, 4 -Iodo-3-benzothienylmethyl group, 5-iodo-3-benzothienylmethyl group, 6-iodo-3-benzothienylmethyl group, 7-iodo-3-benzothienylmethyl group, 2- (4-fluoro-) 2-benzothienyl) ethyl group, 2- (5-fluoro-2-benzothienyl) ethyl group, 2- (6-fluoro-2-benzothienyl) ethyl group, 2- (7-fluoro-2-benzothienyl) Ethyl group, 2- (4-chloro-2-benzothienyl) ethyl group, 2- (5-chloro-2-benzothienyl) ethyl group, 2- (6-chloro-2-benzothi) Enyl) ethyl group, 2- (7-chloro-2-benzothienyl) ethyl group, 2- (4-fluoro-3-benzothienyl) methyl group, 2- (5-fluoro-3-benzothienyl) methyl group, 2- (6-fluoro-3-benzothienyl) ethyl group, 2- (7-fluoro-3-benzothienyl) ethyl group, 2- (4-chloro-3-benzothienyl) ethyl group, 2- (5-) Chloro-3-benzothienyl) ethyl group, 2- (6-chloro-3-benzothienyl) ethyl group, 2- (7-chloro-3-benzothienyl) ethyl group, 2- (4-fluoro-2-benzo) Thienyl) ethyl group, 6- (5-fluoro-2-benzothienyl) hexyl group, 6- (6-fluoro-2-benzothienyl) hexyl group, 6- (7-fluoro-2-benzothienyl) hexyl group, 6 (4-chloro-2-benzothienyl) hexyl group, 6- (5-chloro-2-benzothienyl) hexyl group, 6- (6-chloro-2-benzothienyl) hexyl group, 6- (7-chloro- 2-benzothienyl) hexyl group, 6- (4-fluoro-3-benzothienyl) methyl group, 6- (5-fluoro-3-benzothienyl) hexyl group, 6- (6-fluoro-3-benzothienyl) Hexyl group, 6- (7-fluoro-3-benzothienyl) hexyl group, 6- (4-chloro-3-benzothienyl) hexyl group, 6- (5-chloro-3-benzothienyl) hexyl group, 6- (6-chloro-3-benzothienyl) hexyl group, 6- (7-chloro-3-benzothienyl) hexyl group, (2,4-dibromo-3-benzothienyl) methyl group, (4, 5, 6) Trichloro-3-benzothienyl) can be halogen atoms on a benzofuran ring, such as a methyl group include 1 to 3 substituents and may optionally benzothienyl substituted C1~6 alkyl group.

  A benzofuryl C 2-6 alkenyl group (on the benzofuran ring, at least one of a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group And the species may be substituted) means that 1 to 3 groups selected from unsubstituted or halogen atoms, halogen substituted or unsubstituted C.sub.1-6 alkyl groups and halogen substituted or unsubstituted C.sub.1-6 alkoxy groups are used. A benzofuryl C2-6 alkenyl group, which is a group composed of one substituted benzofuryl and a linear or branched alkenyl group having 1 to 3 carbon atoms and 2 to 6 carbon atoms and having 1 to 3 double bonds; And both cis and cis forms are included. As such a benzofuryl C2-6 alkenyl group, for example, 2-[(2-, 3-, 4-, 5-, 6- or 7-) benzofuryl] vinyl group, 3-[(2-, 3-) , 4-, 5-, 6- or 7-) benzofuryl] 2-propenyl group, 3-[(2-, 3-, 4-, 5-, 6- or 7-) benzofuryl] 2-methyl- 2-propenyl group, 4-[(2-, 3-, 4-, 5-, 6- or 7-) benzofuryl] -2-butenyl group, 4-[(2-, 3-, 4-, 5-] , 6- or 7-) benzofuryl] -3-butenyl group, 4-[(2-, 3-, 4-, 5-, 6- or 7-) benzofuryl] -1,3-butadienyl group, 5- [ (2-, 3-, 4-, 5-, 6- or 7-) benzofuryl] -1,3,5-hexatrienyl group, 6-[(2-, 3-, 4-, 5 , 6- or 7-) benzofuryl] -1,3-hexadienyl group, 3- [6-trifluoromethyl- (2-, 3-, 4-, 5- or 7-) benzofuryl] -2-propenyl group, 3- [5-trifluoromethoxy- (2-, 3-, 4-, 5- or 7-) benzofuryl] -2-propenyl group, 3- [7-chloro- (2-, 3-, 4-, 4-, 5- or 7-) benzofuryl] -2-propenyl group, 3- [2, 6-dimethyl- (3-, 4-, 5- or 7-) benzofuryl] 2-propenyl group, 3- [3, 6 -Dimethoxy- (2-, 3-, 4-, 5- or 7-) benzofuryl] -2-propenyl group, 3- [4,5,6-trimethyl- (2-, 3- or 7-) benzofuryl] -2-propenyl group, 3- [3,5,6-trimethoxy- (2-, 4- or 7-) bene Zofuryl] -2-propenyl group, 3- [3-chloro-6-trifluoromethyl- (2-, 3-, 4-, 5- or 7-) benzofuryl] 2-propenyl group and the like can be mentioned. .

  A thiazolyl group [having at least one phenyl group on the thiazole ring (on the phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group And the like.] May be substituted, for example, (2-, 4- or 5-) thiazolyl group, 4-phenyl- (2 -Or 5-) thiazolyl group, 2-phenyl- (4- or 5-) thiazolyl group, 5-phenyl- (2- or 4-) thiazolyl group, 2, 5-diphenyl-4-thiazolyl group, 2, 4 -Diphenyl-5-thiazolyl group, 2- (4-trifluoromethylphenyl)-(4- or 5-) thiazolyl group, 2- (4-trifluoromethoxyphenyl)-(4- or 5-) Azolyl group, 2- (4-chlorophenyl)-(4- or 5-) thiazolyl group, 2- (3-chloro-4-trifluoromethylphenyl)-(4- or 5-) thiazolyl group, 2- (4) -Methylphenyl)-(4- or 5-) thiazolyl group, 2- (2,4-dimethylphenyl)-(4- or 5-) thiazolyl group, 2- (3,4,6-trimethylphenyl)-( 4- or 5-) thiazolyl group, 2- (4-methoxyphenyl)-(4- or 5-) thiazolyl group, 2- (2,4-dimethoxyphenyl)-(4- or 5-) thiazolyl group, 2 -(3,4,6-trimethoxyphenyl)-(4- or 5-) thiazolyl group, 2- (2,4-dichlorophenyl)-(4- or 5-) thiazolyl group, 2- (3,4,6 6-Trifluorophenyl)-(4- or 5-) Thiazolyl groups such as azolyl groups [1 to 2 phenyl groups on the thiazole ring (on the phenyl ring, halogen atoms, halogen substituted or unsubstituted C1-6 alkyl groups and halogen substituted or unsubstituted C1 And the group selected from the group consisting of 6 alkoxy groups may be substituted by 1 to 5 and preferably 1 to 3).

  Isoindolinyloxy group [C1-6 alkoxycarbonyl group on phenyl group, phenyl C1-6 alkyl group (benzofuryl group on halogen ring, halogen atom, halogen substituted or unsubstituted C1-6 alkyl group on phenyl ring And at least one of a group selected from the group consisting of halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted, phenyl C2-6 alkenyl group (a halogen atom on the phenyl ring, halogen At least one of a group selected from the group consisting of a substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted), a furyl C1-6 alkyl group [ On the furan ring, at least one phenyl group (on the phenyl ring, a halogen atom, halogen substitution or At least one of a group selected from the group consisting of a substituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted), pyridyl C1 To a 6-alkyl group [a pyridine ring, a furyl group and a phenyl group (a phenyl ring, a benzofuryl group, a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 At least one group selected from the group consisting of an alkoxy group and at least one group selected from the group consisting of an alkoxy group may be substituted], benzofuryl C1-6 alkyl group ( On the benzofuran ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alcohol. Or at least one halogen atom may be substituted on the benzothiophene ring (in the benzothiophene ring), at least one of the groups selected from the group consisting of A benzofuryl C2-6 alkenyl group (on the benzofuran ring, a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group At least one member of the thiazolyl group may have at least one phenyl group (a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen atom on the phenyl ring); At least one of a group selected from the group consisting of a substituted or unsubstituted C.sub.1-6 alkoxy group may be substituted) And phenoxy C1-6 alkyl group (on the phenyl ring, a group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group, and a halogen substituted or unsubstituted C1-6 alkoxy group At least one kind of the group selected from the group consisting of at least one kind of the selected group may be substituted], for example, (1-, 2-, 3 -Or 4-) isoindolinyloxy group, 1-tert-butoxycarbonyl- (2-, 3- or 4-) isoindolinyloxy group, 1- [2- (4-chlorophenyl)-(3-, 4) -Or 5-) furylmethyl]-(2-, 3- or 4-) isoindolinyloxy group, 1- [2- (2-chloro-5-trifluoromethylphenyl)-(3-, 4- or- 5-) Frill Group]-(2-, 3- or 4-) isoindolinyloxy group, 1- (3-trifluoromethyl-4-chlorobenzyl)-(2-, 3- or 4-) isoindolinyloxy group, 1- {4-[(2-, 3-, 4-, 5-, 6- or 7-) benzofuryl] benzyl}-(2-, 3- or 4-) isoindolinyloxy group, 1- {3 -[(2- or 3-) furyl]-(2-, 4-, 5- or 6-) pyridylmethyl}-(2-, 3- or 4-) isoindolinyloxy group, 1- [2- (4-Trifluoromethoxyphenyl)-(3-, 4-, 5- or 6-) pyridylmethyl]-(2-, 3- or 4-) isoindolinyloxy group, 1- [2- (3-) Chloro-4-fluorophenyl)-(3-, 4-, 5- or 6-) pyridylmethyl]-(2-, 3- or 3- 4-) Isoindolinyloxy group, 1- [6-trifluoromethyl- (2-, 3-, 4-, 5- or 7-) benzofurylmethyl]-(2-, 3- or 4-) iso Indolinyloxy group, 1- [5-chloro- (2-, 3-, 4-, 6- or 7-) benzothienylmethyl]-(2-, 3- or 4-) isoindolinyloxy group, 1 -[6-chloro- (2-, 3-, 4-, 5-, or 7-) benzofurylmethyl]-(2-, 3- or 4-) isoindolinyloxy group, 1- [5-tri- Fluoromethoxy- (2-, 3-, 4-, 6- or 7-) benzofurylmethyl]-(2-, 3- or 4-) isoindolinyloxy group, 1- {3- [6-trifluoro Methyl- (2-, 3-, 4-, 5- or 7-) benzofuryl] -2-propenyl}-(2-, 3- 4-) isoindolinyloxy group, 1- [5-chloro- (2-, 3-, 4-, 6- or 7-) benzofurylmethyl]-(2-, 3- or 4-) isoindoli Nyloxy group, 1- [2- (4-trifluoromethylphenyl)-(4- or 5-) thiazolylmethyl]-(2-, 3- or 4-) isoindolinyloxy group, 1- [2- (2- 4-Trifluoromethoxyphenoxy) ethyl]-(2-, 3- or 4-) isoindolinyloxy group, 1,3-diethoxycarbonyl- (2- or 4-) isoindolinyloxy group, 2- Phenoxymethyl-4-[(2-, 3-, 4-, 5-, 6- or 7-) benzofurylmethyl]-(1-, 3-, 5-, 6- or 7-) isoindolinyloxy Group, 2-[(2- or 3-) furylmethyl] -4,5-dime An isoindolinyloxy group such as a xycarbonyl- (1-, 3-, 6- or 7-) isoindolinyloxy group [a linear or branched C 1 -C 6 chain or branched chain on an isoindoline ring; C1-6 alkoxycarbonyl group, phenyl C1-6 alkyl group in which the alkyl moiety is a linear or branched alkyl group having 1 to 6 carbon atoms (on the phenyl ring, a benzofuryl group, a halogen atom, halogen substituted or not 1-5, preferably 1 to 3 groups selected from the group consisting of a substituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group may be substituted), an alkenyl moiety A linear or branched alkenyl group having 2 to 6 carbon atoms and 1 to 3 double bonds, and including both a trans form and a cis form; On the ring, 1 to 5, preferably 1 to 3, groups selected from the group consisting of halogen atoms, halogen substituted or unsubstituted C1-6 alkyl groups and halogen substituted or unsubstituted C1-6 alkoxy groups. Optionally substituted), furyl C.sub.1-6 alkyl group wherein the alkyl moiety is a linear or branched alkyl group having 1 to 6 carbon atoms [1 to 3 phenyl groups on the furan ring ( On the phenyl ring, 1 to 5 groups, preferably 1 to 6 groups selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group are preferable. Pyridyl C1-6 alkyl group wherein the alkyl moiety is a linear or branched alkyl group having 1 to 6 carbon atoms] , Furyl and A phenyl group (on the phenyl ring, a group selected from the group consisting of a benzofuryl group, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group is selected from 1 to 5) And preferably 1 to 3 groups may be substituted with 1 to 3 groups selected from the group consisting of 1 to 3), and the alkyl moiety is a linear or branched chain having 1 to 6 carbon atoms Benzofuryl C1-6 alkyl group which is a linear alkyl group (selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group on the benzofuran ring Benzothienyl C.sub.1-6 alkyl group in which the alkyl moiety is a linear or branched alkyl group having 1 to 6 carbon atoms 1 to 3 halogen atoms may be substituted on the benzothiophene ring), a linear or branched alkenyl group having 2 to 6 carbon atoms and 1 to 3 double bonds of the alkenyl moiety. A benzofuryl C2-6 alkenyl group (including a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkyl group on the benzofuran ring, including both a trans form and a cis form) A group selected from the group consisting of 6 alkoxy groups may be substituted by 1 to 3), thiazolyl group [in one or two phenyl groups (on the phenyl ring, halogen atoms on the phenyl ring, 1 to 5, preferably 1 to 3 groups selected from the group consisting of halogen substituted or unsubstituted C1-6 alkyl groups and halogen substituted or unsubstituted C1-6 alkoxy groups Phenyoxy C1-6 alkyl group (which may be substituted) and whose alkyl moiety is a linear or branched alkyl group having 1 to 6 carbon atoms (on the phenyl ring, a halogen) 1 to 5, preferably 1 to 3 groups selected from the group consisting of an atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group Groups selected from the group consisting of (1) may be substituted with 1 to 3 groups].

Benzothiazolidinyloxy group [on the benzothiazolidine ring, an oxo group and a phenyl C.sub.1-6 alkyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or not substituted. At least one group selected from the group consisting of a group selected from the group consisting of a substituted C1-6 alkoxy group] may be substituted] For example, (2-, 3-, 4-, 5-, 6-, or 7-) benzothiazolidinyloxy group, 3- (4-trifluoromethoxybenzyl) -2-oxo- (4-, 5-) , 6- or 7-) benzothiazolidinyloxy group, 3- (4-trifluoromethylbenzyl)-(2-, 4-, 5-, 6- or 7-) benzothiazolidinyloxy group, 3- (4- Rolobenzyl)-(2-, 4-, 5-, 6- or 7-) benzothiazolidinyloxy group, 3- (4-methylbenzyl)-(2-, 4-, 5-, 6- or 7) -) Benzothiazolidinyloxy group, 3- (3,4-dimethylbenzyl)-(2-, 4-, 5-, 6- or 7-) benzothiazolidinyloxy group, 3- (2, 4,6-trimethylbenzyl)-(2-, 4-, 5-, 6- or 7-) benzothiazolidinyloxy group, 3- (4-methoxybenzyl)-(2-, 4-, 5-) , 6- or 7-) benzothiazolidinyloxy group, 3- (3,4-dimethoxybenzyl)-(2-, 4-, 5-, 6- or 7-) benzothiazolidinyloxy group, 3- (3,4,5-trimethoxybenzyl)-(2-, 4-, 5-, 6- or 7-) benzothiazolidinyl Xy group, 3- (4-fluorobenzyl)-(2-, 4-, 5-, 6- or 7-) benzothiazolidinyloxy group, 3- (3,4-dichlorobenzyl)-(2- , 4-, 5-, 6- or 7-) benzothiazolidinyloxy group, 3- (2,4,6-trifluorobenzyl)-(2-, 4-, 5-, 6- or 7- ) Benzothiazolidinyloxy group, 2-oxo- (2-, 4-, 5-, 6- or 7-) benzothiazolidinyloxy group, 2,3-dibenzyl- (4-, 5-, 5-) Benzothiazolidinyloxy such as 6- or 7-benzothiazolidinyloxy group, 2,3,5-tribenzyl- (4-, 5-, 6- or 7-) benzothiazolidinyloxy group Oxo group and the alkyl moiety are linear or branched alkyl having 1 to 6 carbon atoms on the benzothiazolidine ring. Alkyl group (which is selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group on the phenyl ring) A group selected from the group consisting of 1 to 5, preferably 1 to 3 groups may be substituted 1 to 3 groups]
Indolyloxy group [in the indole ring, at least one phenyl C.sub.1-6 alkyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1少 な く と も 6 alkoxy group may be substituted by at least one kind of the group selected from the group consisting of) alkoxy group] may be, for example, (1-, 2-, 3-, 4-, 5-, 6- or 7-) indolyloxy group, 1- (4-trifluoromethoxybenzyl)-(2-, 3-, 4-, 5-, 6- or 7-) indolyloxy group, 1 -(4-trifluoromethylbenzyl)-(2-, 3-, 4-, 5-, 6- or 7-) indolyloxy group, 1- (4-chlorobenzyl)-(2-, 3-,- 4-, 5-, 6- or 7-) indolyl oxi Group, 2- (4-methylbenzyl)-(1-, 3-, 4-, 5-, 6- or 7-) indolyloxy group, 3- (3,4-dimethylbenzyl)-(1-, 2-, 4-, 5-, 6- or 7-) indolyloxy group, 4- (2,4,6-trimethylbenzyl)-(1-, 2-, 3-, 5-, 6- or 7) -) Indolyloxy group, 5- (4-methoxybenzyl)-(1-, 2-, 3-, 4-, 6- or 7-) indolyloxy group, 6- (3,4-dimethoxybenzyl) -(1-, 2-, 3-, 4-, 5- or 7-) indolyloxy group, 7- (3, 4, 5- trimethoxy benzyl)-(1-, 2-, 3-, 4) -, 5- or 6-) indolyloxy group, 1- (4-fluorobenzyl)-(2-, 3-, 4-, 5-, 6- or 7-) indolyloxy group, -(3,4-Dichlorobenzyl)-(2-, 3-, 4-, 5-, 6- or 7-) indolyloxy group, 1- (2,4,6-trifluorobenzyl)-(2 -, 3-, 4-, 5-, 6- or 7-) indolyloxy group, 1,3-dibenzyl- (2-, 4-, 5-, 6- or 7-) indolyloxy group, 1 An indolyloxy group such as 3,5-tribenzyl- (2-, 4-, 6- or 7-) indolyloxy group [in an indole ring, 1 to 3 alkyl moieties have 1 to 6 carbon atoms] (A phenyl atom, a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group on the phenyl ring) which is a straight-chain or branched alkyl group of 1 to 5, preferably 1 to 3 groups selected from the group consisting of groups And the like) may be substituted.

  Pyrrolidinyl group [in the pyrrolidine ring, at least one amino group (on the amino group a C.sub.1-6 alkyl group and a phenyl group (on a phenyl ring a halogen atom, halogen substituted or unsubstituted C.sub.1-6 alkyl Even if at least one group is substituted with a group selected from the group consisting of a group and at least one group selected from the group consisting of a halogen-substituted or unsubstituted C1-6 alkoxy group) For example, 3- [N-methyl-N- (3,4-dichlorophenyl) amino]-(1-, 2-, 4- or 5-) pyrrolidinyl group] , 3-amino- (1-, 2-, 4- or 5-) pyrrolidinyl group, 2,3-diamino- (1-, 4- or 5-) pyrrolidinyl group, 2, 3,5- triamino- (1 -Or 4-) pyrrolidinyl , 3- [N-Methyl-N- (4-methylphenyl) amino]-(1-, 2-, 4- or 5-) pyrrolidinyl group, 3- [N-ethyl-N- (3-methoxyphenyl) Amino]-(1-, 2-, 4- or 5-) pyrrolidinyl group, 3- [N- (4-trifluoromethylphenyl) amino]-(1-, 2-, 4- or 5-) pyrrolidinyl group , 3- [N- (4-trifluoromethoxyphenyl) amino]-(1-, 2-, 4- or 5-) pyrrolidinyl group, 3- [N-methyl-N- (3,4,5-triyl] Fluorophenyl) amino]-(1-, 2-, 4- or 5-) pyrrolidinyl group, 3- [N-methyl-N- (3-chloro-4-trifluoromethylphenyl) amino]-(1-, 2-, 4- or 5-) pyrrolidinyl group, 3- (N-phenylamino)-(1 , 2-, 4- or 5-) pyrrolidinyl group, 3-methylamino- (1-, 2-, 4- or 5-) pyrrolidinyl group, 3-dimethylamino- (1-, 2-, 4- or 5) -) Pyrrolidinyl group such as pyrrolidinyl group [1 to 3 amino groups on the pyrrolidine ring (C1-6 alkyl group on the amino group and phenyl group (on the phenyl ring, halogen atom, halogen substituted or At least one group selected from the group consisting of an unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted ), And preferably 1 to 3 may be substituted).

  Examples of the indolinyl group (in the indoline ring, at least one halogen atom may be substituted) include, for example, (1-, 2-, 3-, 4-, 5-, 6- or 7-) Indolinyl group, 5-bromo- (1-, 2-, 3-, 4-, 6- or 7-) indolinyl group, 4-chloro- (1-, 2-, 3-, 5-, 6- or 7) -) Indolinyl group, 6-fluoro- (1-, 2-, 3-, 4-, 5- or 7-) indolinyl group, 5, 7- dichloro- (1-, 2-, 3-, 4- or- 6-) Indolinyl group such as indolinyl group, 3,5,6-trifluoro- (1-, 2-, 4- or 7-) indolinyl group (1 to 3 halogen atoms are substituted on the indoline ring Can be illustrated).

  Indolinyloxy group [phenyl C1-6 alkyl group on the indoline ring (from the halogen ring, halogen substituted or unsubstituted C1-6 alkyl group and halogen substituted or unsubstituted C1-6 alkoxy group on the phenyl ring As at least one group selected from the group consisting of oxo group and at least one group selected from the group consisting of , 2-, 3-, 4-, 5-, 6- or 7-) indolinyloxy group, 1- (4-trifluoromethoxybenzyl) -2,3-dioxo- (1-, 2-, 3-) , 4-, 5-, 6- or 7-) indolinyloxy group, 1- (4-trifluoromethoxybenzyl) -2-oxo- (3-, 4-, 5-, 6- or 7-) indoli. Nyloxy group, 1- (4) Trifluoromethylbenzyl)-(2-, 3-, 4-, 5-, 6- or 7-) indolinyloxy group, 1- (4-chlorobenzyl)-(2-, 3-, 4-, 5 -, 6 or 7-) indolinyloxy group, 3- (4-methylbenzyl)-(1-, 2-, 4-, 5-, 6- or 7-) indolinyloxy group, 4- (3) 4-Dimethylbenzyl)-(1-, 2-, 3-, 5-, 6- or 7-) indolinyloxy group, 2- (2,4,6-trimethylbenzyl)-(1-, 3-) , 4-, 5-, 6- or 7-) indolinyloxy group, 5- (4-methoxybenzyl)-(1-, 2-, 3-, 4-, 6- or 7-) indolinyloxy group , 6- (3,4-dimethoxybenzyl)-(1-, 2-, 3-, 4-, 5- or 7-) indolinyloxy group, 7- 3,4,5-trimethoxybenzyl)-(1-, 2-, 3-, 4-, 5- or 6-) indolinyloxy group, 1- (4-fluorobenzyl)-(2-, 3-) , 4-, 5-, 6- or 7-) indolinyloxy group, 1- (3,4-dichlorobenzyl)-(2-, 3-, 4-, 5-, 6- or 7-) indolinyl Oxy group, 1- (2,4,6-trifluorobenzyl)-(2-, 3-, 4-, 5-, 6- or 7-) indolinyloxy group, 2-oxo- (1-, 3) -, 4-, 5-, 6- or 7-) indolinyloxy group, 1,3-dibenzyl- (2-, 4-, 5-, 6- or 7-) indolinyloxy group, 1, 5, 5 6-tribenzyl- (1-, 2-, 3-, 4- or 7-) indolinyloxy group, 2,3-dioxo- (1-, 4-, 5-, 6- or Is an indolinyloxy group such as a 7-) indolinyloxy group [on an indoline ring, a phenyl C.sub.1-6 alkyl group in which the alkyl moiety is a linear or branched alkyl group having 1 to 6 carbon atoms (on the phenyl ring 1 to 5, preferably 1 to 3 groups selected from the group consisting of halogen atoms, halogen-substituted or unsubstituted C1-6 alkyl groups and halogen-substituted or unsubstituted C1-6 alkoxy groups And the group selected from the group consisting of oxo group and oxo group may be substituted with 1 to 3 groups].

  The method for producing the compound of the present invention is shown below.

[Wherein, R ¹ , R ² and n are as defined above. X ¹ represents a halogen atom or a nitro group. ]
According to reaction process formula 1, the compound of the present invention represented by the general formula (1) can be obtained by reacting a 4-nitroimidazole compound represented by the general formula (2) in the presence or absence of a basic compound Prepared by reacting the compound represented by the general formula (3a) with the epoxy compound represented by the general formula (3a) to obtain a compound represented by the general formula (4a) and then ring-closing the compound represented by the general formula (4a) obtained Ru.

  The ratio of the compound of the general formula (2) to the compound of the general formula (3a) is usually 0.5 to 5 times by mole, preferably 0.5 to 3 times by mole of the latter. .

  As the basic compound, known compounds can be widely used, and examples thereof include inorganic basic compounds such as metal hydrides, metal alcoholates, hydroxides, carbonates and hydrogencarbonates, organic basic compounds such as acetates, etc. Be

  Specific examples of the metal hydride include sodium hydride and potassium hydride. Specific examples of metal alcoholates include sodium methoxide, sodium ethoxide, potassium tert-butoxide and the like. Specific examples of the hydroxide include sodium hydroxide and potassium hydroxide. Specific examples of the carbonate include sodium carbonate and potassium carbonate. Specific examples of the hydrogen carbonate include sodium hydrogen carbonate and potassium hydrogen carbonate. Inorganic basic compounds include sodium amide and the like in addition to the above.

  Specific examples of the acetate include sodium acetate, potassium acetate and the like. Specific examples of the organic basic compounds other than the above include triethylamine, trimethylamine, diisopropylethylamine, pyridine, dimethylaniline, 1-methylpyrrolidine, N-methylmorpholine, 1,5-diazabicyclo [4.3.0] nonene -5 (DBN), 1, 8- diaza bicyclo [5. 4.0] undecene 7 (DBU), 1, 4- diaza bicyclo [2.2.2] octane (DABCO), etc. can be illustrated.

  Such a basic compound is used usually 0.1 to 2 times mol, preferably 0.1 times to equimol, more preferably 0.1 to 0.5 times mol of the compound of the general formula (2) That's good.

  The reaction of the compound of the general formula (2) with the compound of the general formula (3a) is usually carried out in a suitable solvent.

  As the solvent, widely known solvents can be used as long as they do not inhibit the reaction. Examples of such a solvent include aprotic polar solvents such as dimethylformamide (DMF), dimethylsulfoxide (DMSO), and acetonitrile, ketone solvents such as acetone and methyl ethyl ketone, benzene, toluene, xylene, tetralin, liquid paraffin, etc. Hydrocarbon solvents such as methanol, ethanol, isopropanol, alcohol solvents such as n-butanol and tert-butanol, tetrahydrofuran (THF), ether solvents such as dioxane, dipropyl ether, diethyl ether and diglyme, ethyl acetate, acetic acid Examples thereof include ester solvents such as methyl, mixed solvents thereof and the like. These solvents may contain water.

  The reaction of the compound of the general formula (2) with the compound of the general formula (3a) can be carried out, for example, by dissolving the compound of the general formula (2) in a reaction solvent and stirring under ice cooling or at room temperature (30 ° C) while stirring. A basic compound is added, and after stirring for 30 minutes to 1 hour at room temperature to 80 ° C., a compound of the general formula (3a) is added, usually for 30 minutes to 60 hours, preferably at room temperature to 100 ° C., preferably 50 to 80 ° C. Is carried out by continuing stirring for 1 to 50 hours.

  The compound (2) used as a raw material is a known compound. The compound (3a) includes a novel compound, and the method for producing the compound will be described later.

  The reaction mixture thus obtained is, for example, cooled, and then the crude reaction product is separated by an isolation operation such as filtration, concentration, extraction and the like, and by a general purification operation such as column chromatography and recrystallization. The compound of formula (4a) can be isolated and purified from the reaction mixture.

  The compound of the present invention represented by the general formula (1) is produced by subjecting the compound represented by the general formula (4a) to a ring closure reaction. The ring closure reaction is carried out by dissolving the compound represented by the general formula (4a) obtained above in a reaction solvent, adding a basic compound and stirring.

  As the reaction solvent and the basic compound, the same reaction solvents and basic compounds as those used in the reaction of the compound of the general formula (2) with the compound of the general formula (3a) can be used.

  The amount of the basic compound to be used is generally equimolar to excess molar, preferably 1 to 5 times molar, more preferably 1 to 2 times molar relative to the compound of general formula (4a).

  The reaction temperature of the ring closure reaction is usually 0 to 150 ° C., preferably room temperature to 120 ° C., more preferably 50 to 100 ° C. The reaction time is usually 30 minutes to 48 hours, preferably 1 to 24 hours, more preferably 1 to 12 hours.

  The reaction mixture thus obtained is, for example, cooled, and then the crude reaction product is separated by an isolation operation such as filtration, concentration, extraction and the like, and by a general purification operation such as column chromatography and recrystallization. The compound of formula (1) can be isolated and purified from the reaction mixture.

  In the present invention, the reaction mixture may be subjected to subsequent ring-closing reaction without isolation of the compound of the general formula (4a) formed by the reaction of the compound of the general formula (2) and the compound of the general formula (3a). it can. For example, after reacting the compound of the general formula (2) with the compound of the general formula (3a) at room temperature to 80 ° C., a basic compound is added to the reaction mixture, and stirring is further performed at 50 to 100 ° C. Alternatively, after reacting the compound of the general formula (2) with the compound of the general formula (3a) at room temperature to 80 ° C., the reaction mixture is concentrated, the residue is dissolved in a high boiling point solvent, and the resulting solution is basic The target compound represented by General formula (1a) can also be manufactured by adding a compound and performing stirring further at 50-100 degreeC.

  In addition, in the reaction of the compound of the general formula (2) with the compound of the general formula (3a), the basic compound is used at 0.9 to 2 times mol of the compound (2) and stirred at 50 to 100 ° C. Thus, the compound of general formula (2) can be reacted with the compound of general formula (3a) at once to produce the target compound of general formula (1a).

[Wherein, X ¹ is the same as the above. R ^1a represents a hydrogen atom or a C1 to 6 alkyl group. R ^2a represents a group represented by general formula (A), (B), (E) or (F) or a group represented by the above (a) or (y). ]
According to Reaction scheme-2, the compound of the present invention represented by the general formula (1b) is represented by the compound represented by the general formula (3b) and the general formula (5) in the presence of a basic compound The compound represented by the general formula (4b) is obtained by reacting the compound or the salt thereof, and then the compound represented by the general formula (4b) obtained is subjected to ring closure.

The compound (3b) is a novel compound, and the method for producing the compound will be described later (Scheme 13). Further, a compound (5) in which R ^2a represents a group represented by the general formula (E) includes a novel compound, and one example of a method for producing the compound is described in Reference Example 182, Reference Example 186 to Reference Example 188 described later. Reference Example 192 and Reference Example 449 are shown.

  The ratio of the compound of the general formula (3b) to the compound of the general formula (5) is usually 0.5 to 5 moles, preferably 0.5 to 2 moles of the latter with respect to the former. .

  The reaction of the compound of the general formula (3b) with the compound of the general formula (5) is carried out in a suitable solvent in the presence of a basic compound.

  As the basic compound and the reaction solvent, the same basic compounds and reaction solvents as those used in the reaction of the compound of the general formula (2) with the compound of the general formula (3a) can be used. The amount of the basic compound used is usually a catalytic amount, preferably 0.1 to 3 times mol, more preferably 0.1 to 2 times mol, of the compound of the general formula (3b).

In the case of a compound (5) in which R ^2a represents a group represented by general formula (B) or (E), a salt of the compound (5) is used instead of using the compound (5) and the basic compound be able to. Such salts include alkali metal salts such as sodium salt and potassium salt of compound (5).

  The reaction of the compound of the general formula (3b) with the compound of the general formula (5) is performed usually at room temperature to 150 ° C., preferably at room temperature to 120 ° C., more preferably at room temperature to 80 ° C. The reaction time is generally 10 minutes to 48 hours, preferably 10 minutes to 24 hours, and more preferably 10 minutes to 2 hours.

  The reaction mixture thus obtained is, for example, cooled, and then the crude reaction product is separated by an isolation operation such as filtration, concentration, extraction and the like, and by a general purification operation such as column chromatography and recrystallization. The compound of formula (4b) can be isolated and purified from the reaction mixture.

  The compound of the present invention represented by the general formula (1b) is produced by subjecting the compound represented by the general formula (4b) to a ring closure reaction. The ring closure reaction is carried out by dissolving the compound represented by the general formula (4b) obtained above in a reaction solvent, adding a basic compound, and stirring at a predetermined temperature.

  As the reaction solvent and the basic compound, the same reaction solvents and basic compounds as those used in the reaction of the compound of the general formula (3b) with the compound of the general formula (5) can be used.

  The amount of the basic compound to be used is generally equimolar to excess molar, preferably equimolar to 5 times molar, more preferably equimolar to double molar relative to the compound of the general formula (4b).

  The reaction temperature of the ring closure reaction is usually 0 to 150 ° C., preferably room temperature to 120 ° C., more preferably 50 to 100 ° C. The reaction time is generally 10 minutes to 48 hours, preferably 10 minutes to 24 hours, and more preferably 20 minutes to 4 hours.

  The reaction mixture thus obtained is, for example, cooled, and then the crude reaction product is separated by an isolation operation such as filtration, concentration, extraction and the like, and by a general purification operation such as column chromatography and recrystallization. The compound of formula (1b) can be isolated and purified from the reaction mixture.

  In the present invention, the reaction mixture may be subjected to the subsequent ring-closing reaction without isolation of the compound of the general formula (4b) formed by the reaction of the compound of the general formula (3b) with the compound of the general formula (5). Thus, it is also possible to produce the desired compound of the present invention represented by the general formula (1b).

In particular, in the case of compound (5) in which R ^2a represents a group represented by general formula (B) or (E), the basic compound is used in equimolar to excess molar with respect to compound (5), 50 to 100 If the reaction is carried out at ° C., the present compound of the general formula (1 b) is produced at once without isolation of the intermediate (4). The same applies to the case where an alkali metal salt (e.g., a sodium salt or a potassium salt) of a compound (5) in which R ^2a represents a group represented by general formula (B) or (E) is used.

[Wherein, R ⁴¹ and X ¹ are as defined above. ]
According to Reaction scheme-3, the compound of the present invention represented by the general formula (1c) is represented by the compound represented by the general formula (2) and the general formula (3c) in the presence of a basic compound The compound represented by the general formula (4c) is reacted with a compound to give a compound, and then the compound represented by the general formula (4c) obtained is subjected to ring closure.

  The compound (3c) includes a novel compound, and the method for producing the compound will be described later (Scheme 14).

  The ratio of the compound of the general formula (2) to the compound of the general formula (3c) is usually 0.1 to 2 moles, preferably 0.1 to 1 mole, more preferably 0 moles of the former with respect to the latter. It is good to make it 1-0.5 times mole.

  The reaction of the compound of the general formula (2) with the compound of the general formula (3c) is carried out in a suitable solvent in the presence of a basic compound.

  As the basic compound and the reaction solvent, the same basic compounds and reaction solvents as those used in the reaction of the compound of the general formula (2) with the compound of the general formula (3a) can be used. The amount of the basic compound to be used is generally 0.1 times mol to excess mol, preferably 1 to 5 times mol, more preferably 1 to 2 times mol, of the compound of the general formula (2).

  The reaction of the compound of the general formula (2) with the compound of the general formula (3c) is carried out, for example, by dissolving the compound of the general formula (2) in a reaction solvent and stirring under ice cooling or at room temperature (30 ° C.) while stirring. A basic compound is added, and after stirring for 30 minutes to 1 hour at room temperature to 80 ° C., a compound of the general formula (3c) is added, usually for 30 minutes to 24 hours, preferably at room temperature to 100 ° C., preferably 50 to 80 ° C. Is carried out by continuing the stirring for 1 to 12 hours, more preferably 1 to 8 hours.

  The reaction mixture thus obtained is, for example, cooled, and then the crude reaction product is separated by an isolation operation such as filtration, concentration, extraction and the like, and by a general purification operation such as column chromatography and recrystallization. The compound of formula (4c) can be isolated and purified from the reaction mixture.

  The compound of the present invention represented by the general formula (1c) is produced by subjecting the compound represented by the general formula (4c) to a ring closure reaction. The ring closure reaction is carried out by dissolving the compound represented by the general formula (4c) obtained above in a reaction solvent, adding a basic compound, and stirring at a predetermined temperature.

  As the reaction solvent and the basic compound, the same reaction solvents and basic compounds as those used in the reaction of the compound of the general formula (2) with the compound of the general formula (3c) can be used.

  The amount of the basic compound to be used is generally equimolar to excess molar, preferably 1 to 5 moles, more preferably 1 to 2 moles, per mole of the compound of the general formula (4c).

  The reaction temperature of the ring closure reaction is usually 0 to 150 ° C., preferably room temperature to 120 ° C., more preferably 50 to 100 ° C. The reaction time is usually 30 minutes to 48 hours, preferably 1 to 24 hours, more preferably 1 to 12 hours.

  The reaction mixture thus obtained is, for example, cooled, and then the crude reaction product is separated by an isolation operation such as filtration, concentration, extraction and the like, and by a general purification operation such as column chromatography and recrystallization. The compound of formula (1c) can be isolated and purified from the reaction mixture.

  In the present invention, the reaction mixture may be subjected to the subsequent ring-closing reaction without isolation of the compound of the general formula (4c) formed by the reaction of the compound of the general formula (2) with the compound of the general formula (3c). Thus, it is also possible to produce the desired compound of the present invention represented by the general formula (1c).

[Wherein, R ^1a and n are as defined above. R ^3a represents a C1-6 alkoxy-C1-6 alkyl group. R ^3b represents a C1 to 6 alkanoyl group. ]
In the general formula (1), a compound in which R ² represents a group represented by general formula (A) and R ³ represents a hydrogen atom of A 1 (hereinafter referred to as “compound (1-A-A1)”) is corresponding compounds exhibiting C1~6 alkoxy -C1~6 alkyl group R ³ is A3) (hereinafter "compound (1-a-A3)" hereinafter) or a compound showing a C1~6 alkanoyl group R ³ is A9) It manufactures by hydrolyzing (Hereinafter, it is called "compound (1-A-A9).").

  The hydrolysis of compound (1-A-A3) is performed under acidic conditions. For example, the reaction can be performed by adding an acid to a solution in which compound (1-A-A3) is suspended or dissolved in a suitable solvent, and stirring at 0 to 120 ° C. Examples of the solvent used include water, methanol, ethanol, isopropanol, alcohol solvents such as ethylene glycol, acetonitrile, acetone, toluene, DMF, DMSO, acetic acid, trifluoroacetic acid, mixed solvents of these, and the like. . Examples of the acid to be used include organic acids such as trifluoroacetic acid and acetic acid, and inorganic acids such as hydrochloric acid, bromic acid, hydrobromic acid and sulfuric acid. Organic acids such as trifluoroacetic acid and acetic acid can themselves be used as reaction solvents. The reaction temperature is usually 0 to 120 ° C., preferably room temperature to 100 ° C., more preferably room temperature to 80 ° C. The reaction time is usually 30 minutes to 24 hours, preferably 30 minutes to 12 hours, and more preferably 1 to 8 hours.

  The hydrolysis of compound (1-A-A9) is performed under basic conditions. For example, the reaction can be performed by adding a base to a solution in which compound (1-A-A9) is suspended or dissolved in a suitable solvent, and stirring at 0 to 120 ° C. The solvent to be used is, for example, water, alcohol solvents such as methanol, ethanol, isopropanol, ethylene glycol and the like, or a mixed solvent thereof. Examples of the base to be used include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; and acetates such as sodium acetate. The reaction temperature is 0 to 120 ° C., preferably room temperature to 100 ° C., more preferably room temperature to 80 ° C. The reaction time is 30 minutes to 24 hours, preferably 30 minutes to 12 hours, and more preferably 1 to 8 hours.

  The reaction mixture thus obtained is, for example, cooled, and then the crude reaction product is separated by an isolation operation such as filtration, concentration, extraction and the like, and the compound is produced by a usual purification operation such as column chromatography and recrystallization. (1-A-A1) can be isolated and purified from the reaction mixture.

[Wherein, R ^1a and n are as defined above. X ² represents a halogen atom. ^R3aa represents a C1-6 alkyl group or a phenyl group which may be substituted by a C1-6 alkyl group. ]
In the general formula (1), R ² is a group represented by the general formula (A), and R ³ is C ¹ to 6 alkylsulfonyl group of A 7) and C ¹ to 6 alkyl group of A 8) A compound exhibiting a good benzenesulfonyl group (hereinafter referred to as "compound (1-A-A7)" sulfonylates a compound (compound (1-A-A1)) in which the corresponding R ³ represents a hydrogen atom of A1) Manufactured by

  Here, a C1-6 alkylsulfonyl group is a group constituted by an alkyl group having 1 to 6 carbon atoms and a sulfonyl group, and examples thereof include a methanesulfonyl group, an ethanesulfonyl group, a propanesulfonyl group, A butane sulfonyl group, a pentane sulfonyl group, a hexane sulfonyl group etc. can be mentioned.

  The benzenesulfonyl group which may be substituted by a C1-6 alkyl group is, for example, benzenesulfonyl group, o-toluenesulfonyl group, m-toluenesulfonyl group, p-toluenesulfonyl group, 2-ethylbenzenesulfonyl group, 3- Ethylbenzenesulfonyl group, 4-ethylbenzenesulfonyl group, 2-propylbenzenesulfonyl group, 3-propylbenzenesulfonyl group, 4-propylbenzenesulfonyl group, 2,3-dimethylbenzenesulfonyl group, 2,4-dimethylbenzenesulfonyl group, 2 Mention may be made of a benzenesulfonyl group in which 1 to 3 C1-6 alkyl groups such as 4, 6, 4-trimethylbenzenesulfonyl group may be substituted.

The reaction conditions of the sulfonylation reaction of the alcohol generally performed are widely applicable to the sulfonylation of compound (1-A-A1). For example, the compound (1-A-A1) is dissolved in a suitable solvent, and to this solution is added a compound represented by the general formula R ^3aa SO ₂ X ² in the presence of a basic compound, and the mixture is stirred at 0-150 ° C. The compound (1-A-A7) can be obtained by

  Any solvent can be used as long as it does not inhibit the sulfonylation reaction. Examples of such solvents include halogenated hydrocarbon solvents such as methylene chloride and chloroform, aprotic polar solvents such as DMF, DMSO and acetonitrile, aromatic hydrocarbon solvents such as benzene, toluene and xylene, and tetralin Liquid paraffin, hydrocarbon solvents such as cyclohexane, THF, dioxane, dipropyl ether, ether solvents such as diethyl ether, diglyme, etc., ethyl acetate, acetone, etc., or mixed solvents of these, etc. may be mentioned.

The compound represented by the general formula R ^3aa SO ₂ X ² is generally equimolar to excess molar, preferably equimolar to 2-fold molar, more preferably equimolar to 1-fold relative to the compound (1-A-A1). .1 mole may be used.

  As the basic compound, the same basic compounds as those used in the reaction of the compound of the above general formula (2) with the compound of the general formula (3a) can be used.

The amount of the basic compound used is usually equimolar to excess molar, preferably 1 to 5 times molar, more preferably 1 to 2 times molar relative to the compound represented by the general formula R ^3aa SO ₂ X ² .

  In the sulfonylation reaction, 4-dimethylaminopyridine, 4- (1-pyrrolidinyl) pyridine and the like can also be used as a catalyst.

  The reaction temperature is usually 0 to 150 ° C, preferably 0 to 100 ° C, and more preferably 0 to 60 ° C. The reaction time is usually 30 minutes to 48 hours, preferably 1 to 24 hours, more preferably 1 to 4 hours.

  The reaction mixture thus obtained is, for example, cooled, and then the crude reaction product is separated by an isolation operation such as filtration, concentration, extraction and the like, and the compound is produced by a usual purification operation such as column chromatography and recrystallization. (1-A-A7) can be isolated and purified from the reaction mixture.

[Wherein, R ^1a , R ^2a , R ^3aa and n are as defined above. ]
Compounds represented by general formula (1) in which R ² represents a group represented by general formula (A), (B), (E) or (F) or a group represented by (a) to (y) “Compound (1b)” represents a group in which R ² is represented by general formula (A), and the corresponding R ³ is a C1-6 alkylsulfonyl group of A7) and a C1-6 alkyl group of A8) It is also produced by reacting a compound (compound (1-A-A7)) showing a benzenesulfonyl group which may be substituted with a compound represented by the general formula (5).

  The reaction of compound (1-A-A7) with the compound represented by the general formula (5) is carried out in a suitable solvent in the presence of a basic compound.

  Any solvent can be used as long as it does not inhibit the reaction. Examples of such a solvent include aprotic polar solvents such as water, DMF, DMSO and acetonitrile, hydrocarbon solvents such as benzene, toluene, xylene, tetralin, liquid paraffin and cyclohexane, ethanol, isopropanol and n-butanol Alcohol solvents such as tert-butanol, ether solvents such as THF, dioxane, dipropyl ether, diethyl ether and diglyme, ethyl acetate, acetone and the like, or mixed solvents of these, and the like can be mentioned.

  As the basic compound, the same basic compounds as those used in the reaction of the compound of the above general formula (2) with the compound of the general formula (3a) can be used.

  The amount of the basic compound to be used is generally equimolar to molar excess, preferably 1 to 5 times molar, more preferably 1 to 2 times molar relative to the compound (1-A-A7).

  The compound represented by the general formula (5) is generally equimolar to excess molar, preferably 0.9 to 2-fold molar, more preferably 0.9 to 1. The compound (1-A-A7). A 5-fold molar amount may be used.

  The reaction temperature is usually room temperature to 150 ° C., preferably room temperature to 100 ° C., more preferably 60 to 100 ° C. The reaction time is generally 10 minutes to 24 hours, preferably 10 minutes to 12 hours, and more preferably 20 minutes to 7 hours.

  The reaction mixture thus obtained is, for example, cooled, and then the crude reaction product is separated by an isolation operation such as filtration, concentration, extraction and the like, and the objective is obtained by a usual purification operation such as column chromatography and recrystallization. The compounds can be isolated and purified from the reaction mixture.

[Wherein, R ^1a , n, R ⁷ and R ⁸ are as defined above. ]
In the general formula (1), a compound in which R ² represents a group represented by the general formula (D) (hereinafter referred to as “compound (1-D)”) is a group in which R ² is represented by the general formula (A) And R ³ is a hydrogen atom of A1) (compound (1-A-A1)), which is produced by carbamateing.

The reaction conditions of the carbamate reaction of alcohol generally carried out can be widely applied to the carbamate formation of the compound (1-A-A1). As such a method, for example, (i) a method using an amine represented by the general formula R ⁷ R ⁸ NH (wherein R ⁷ and R ⁸ are the same as above) and triphosgene, (ii) a general formula R ^A reaction using an amine and a carbodiimidazole represented by ⁷ R ⁸ NH (wherein R ⁷ and R ⁸ are as defined above), a method using an (iii) isocyanate compound, and the like can be mentioned.

(i) Method using amine and triphosgene:
When triphosgene is allowed to act on the amine represented by the general formula R ⁷ R ⁸ NH (wherein R ⁷ and R ⁸ are as defined above), the general formula ClCONR ⁷ R ⁸ (wherein R ⁷ and R ⁸ are the above-mentioned) The same carbamic acid chloride represented by The carbamic acid chloride may be isolated but is generally used as it is in the next step without isolation because it is generally unstable.

  To a methylene chloride solution of triphosgene under cooling and stirring, the basic compound and the above amine are added, and the mixture is stirred at 0-30 ° C. for 30 minutes to 4 hours to generate carbamic acid chloride. The use amount of triphosgene is usually 0.3 to 1.5 times mol, preferably 0.3 to 0.6 times mol, more preferably 0.3 to 0.4 times mol based on the amine.

  As a basic compound used in reaction of an amine and triphosgene, a triethylamine, N-ethyldiisopropylamine, N- methyl morpholine etc. are mentioned, for example. These basic compounds are used in a 3-fold molar to excess molar, preferably 3-4.5-fold molar, more preferably 3-3.3-fold molar, with respect to triphosgene.

  The reaction temperature is usually 0 to 60 ° C., preferably 0 ° C. to room temperature (30 ° C.), and the reaction time is usually 30 minutes to 8 hours, preferably 1 to 4 hours, more preferably 1 to 2 hours .

  The reaction solution of carbamic acid chloride thus obtained can be used as it is, but it is more advantageous to remove insolubles by filtration and to concentrate the filtrate.

  Next, the compound (1-A-A1) is dissolved in a suitable reaction solvent, and the carbamic acid chloride prepared above is added under ice-cooling and stirring, and then cuprous chloride is added, and then further added at a predetermined temperature for a predetermined time Compound (1-D) can be produced by stirring.

  As a reaction solvent which can be used here, a solvent which does not inhibit the reaction can be widely used. As such solvent, for example, aprotic polar solvents such as DMF, DMSO and acetonitrile, hydrocarbon solvents such as benzene, toluene, xylene, tetralin and liquid paraffin, halogenated carbons such as methylene chloride, chloroform and dichloroethane Examples thereof include hydrogen solvents, ether solvents such as THF, dioxane, dipropyl ether, diethyl ether, diglyme and the like, acetone, ethyl acetate, and the above mixed solvents and the like.

  The carbamic acid chloride is used usually equimolar to 5 times molar, preferably equimolar to 3-fold molar, more preferably equimolar to 2-fold molar relative to the compound (1-A-A1).

  The cuprous chloride is usually 0.1 to 5 times mol, preferably 0.5 to 2 times mol, more preferably 0.5 times to 1 mol of the compound (1-A-A1). You may use it.

  The reaction temperature is generally 0 to 60 ° C, preferably 10 to 50 ° C, and more preferably 20 to 35 ° C. The reaction time is usually 30 minutes to 48 hours, preferably 1 to 30 hours, more preferably 2 to 24 hours.

(ii) Reaction with amine and carbodiimidazole:
An amine represented by the general formula R ⁷ R ⁸ NH (wherein R ⁷ and R ⁸ are the same as above) is dissolved in a suitable reaction solvent, into which 1,1'-carbonyldiimidazole is stirred under ice cooling. Is added and the mixture is stirred at a predetermined temperature for a predetermined time to obtain an aminocarbonylimidazole derivative.

  The amount of 1,1'-carbonyldiimidazole to be used is generally 0.9 to 2 moles, preferably 1 mole to 1.5 moles, more preferably 1 mole to 1.2 moles per mole of the amine. It is a mole.

  Solvents used include aprotic polar solvents such as acetonitrile, hydrocarbon solvents such as benzene, toluene, xylene, tetralin and liquid paraffin, halogenated hydrocarbon solvents such as methylene chloride, chloroform and dichloroethane, THF, dioxane Examples thereof include ether solvents such as dipropyl ether, diethyl ether and diglyme, acetone, ethyl acetate, and the above mixed solvent.

  The reaction temperature is usually 0 to 60 ° C., preferably 0 ° C. to room temperature (30 ° C.), and the reaction time is usually 30 minutes to 8 hours, preferably 1 to 4 hours, more preferably 1 to 2 hours .

  Next, the compound (1-A-A1) is previously dissolved in a suitable solvent, the aminocarbonylimidazole derivative obtained above is added to this with stirring under ice-cooling, cuprous chloride is further added, and the mixture is heated to a predetermined temperature The compound (1-D) can be produced by stirring for a period of time.

  As a reaction solvent which can be used here, a solvent which does not inhibit the reaction can be widely used. As such solvent, for example, aprotic polar solvents such as DMF, DMSO and acetonitrile, hydrocarbon solvents such as benzene, toluene, xylene, tetralin and liquid paraffin, halogenated carbons such as methylene chloride, chloroform and dichloroethane Examples thereof include hydrogen solvents, ether solvents such as THF, dioxane, dipropyl ether, diethyl ether, diglyme and the like, acetone, ethyl acetate, and the above mixed solvents and the like.

  The aminocarbonylimidazole derivative is generally used in equimolar to 5 times molar, preferably equimolar to 3-fold molar, more preferably equimolar to 2-fold molar relative to the compound (1-A-A1).

  In addition, the amount of cuprous chloride used is usually 0.9 to 5 times mol, preferably 1 mol to 2 times mol, more preferably 1 mol to 1.2 times mol of the compound (1-A-A1). do it.

  The reaction temperature is generally 0 to 60 ° C, preferably 10 to 50 ° C, and more preferably 20 to 35 ° C. The reaction time is usually 30 minutes to 48 hours, preferably 1 to 30 hours, more preferably 1 to 3 hours.

(iii) Method using isocyanate:
The compound (1-A-A1) is dissolved in a suitable reaction solvent, isocyanates are added thereto with ice-cooling and stirring, cuprous chloride is further added, and stirring is carried out at a predetermined temperature for a predetermined time. R ⁷ or R ⁸ can be produced a compound a hydrogen atom (1-D).

  As a reaction solvent which can be used here, a solvent which does not inhibit the reaction can be widely used. As such solvent, for example, aprotic polar solvents such as DMF, DMSO and acetonitrile, hydrocarbon solvents such as benzene, toluene, xylene, tetralin and liquid paraffin, halogenated carbons such as methylene chloride, chloroform and dichloroethane Examples thereof include hydrogen solvents, ether solvents such as THF, dioxane, dipropyl ether, diethyl ether, diglyme and the like, acetone, ethyl acetate, and the above mixed solvents and the like.

  The isocyanates may be used in an amount of usually 1 to 5 moles, preferably 1 to 3 moles, more preferably 1 to 2 moles, per mole of the compound (1-A-A1).

  In addition, the amount of cuprous chloride used is usually 0.9 to 5 times mol, preferably 1 mol to 2 times mol, more preferably 1 mol to 1.2 times mol of the compound (1-A-A1). do it.

  The reaction temperature is generally 0 to 60 ° C, preferably 10 to 50 ° C, and more preferably 20 to 35 ° C. The reaction time is usually 30 minutes to 48 hours, preferably 1 to 30 hours, more preferably 1 to 3 hours.

  For example, after cooling the reaction mixture obtained by the method of the above (i), (ii) or (iii), the crude reaction product is separated by an isolation operation such as filtration, concentration, extraction and the like, and column chromatography Compound (1-D) can be isolated and purified from the reaction mixture by ordinary purification procedures such as recrystallization and the like.

  In the compound of the present invention of the general formula (1), a compound having a heterocycle containing a nitrogen atom in the molecule and having a nitrogen atom on the heterocycle substituted with a C1 to 6 alkoxycarbonyl group is deprotected Can lead to a compound in which a nitrogen atom on the corresponding heterocycle is substituted by a hydrogen atom.

  In this method, for example, the target compound can be obtained by dissolving the raw material compound to be deprotected in a suitable reaction solvent and hydrolyzing using an acid.

  As a reaction solvent which can be used here, a solvent which does not inhibit the reaction can be widely used. Examples of such solvents include water, alcohol solvents such as methanol and ethanol, aprotic polar solvents such as DMSO and acetonitrile, hydrocarbon solvents such as benzene, toluene, xylene, tetralin and liquid paraffin, methylene chloride Examples thereof include halogenated hydrocarbon solvents such as chloroform and dichloroethane, ether solvents such as THF, dioxane, dipropyl ether, diethyl ether and diglyme, acetone, ethyl acetate, and the above mixed solvents.

  Examples of the acid include inorganic acids such as hydrochloric acid, bromic acid and hydrobromic acid, and organic acids such as trifluoroacetic acid, trichloroacetic acid and acetic acid. Among these, trifluoroacetic acid is preferably used.

  The amount of these acids used is usually at least equimolar, preferably 2 to 10 times the molar amount of the raw material compound, but these acids may be used in a large excess as a reaction solvent. The reaction temperature is usually room temperature to 100 ° C., but may be appropriately adjusted depending on the type of acid used. If trifluoroacetic acid is used, room temperature is sufficient. The reaction time is usually 1 to 24 hours, preferably 1 to 12 hours.

  The reaction mixture thus obtained can be concentrated, and if necessary, it can be crystallized by adding an acid such as hydrochloric acid, and the target compound in the form of hydrochloride or trifluoroacetate can be isolated by recrystallization or the like.

  The deprotected target compound can be isolated as described above, but without isolation, a basic compound such as triethylamine is added to lead to a free form of the target compound, which is then It can be used for the reaction.

  For example, the corresponding amide or carbamate can be produced by reacting an acid halide, an acid anhydride or a mixed acid anhydride with the target compound in free form. The corresponding sulfonic acid amide can be prepared by reacting the free form of the above target compound with a sulfonic acid chloride. The corresponding urea can be prepared by ureazing the free form of the above target compound with an amine. Furthermore, the reductive amination reaction using an aldehyde or an alkylation reaction with an alkyl halide can be used to produce an N-alkylated form of the above target compound.

In the compound of the present invention of the general formula (1), a compound having a heterocycle containing a nitrogen atom in the molecule, and having a nitrogen atom on the heterocycle substituted with a hydrogen atom, corresponds by carbamateing the compound A nitrogen atom on the heterocycle can be derived to a compound in which a -COOR ²⁷ group (R ²⁷ is the same as above) is substituted.

  Examples of the carbamate method include (i) methods using various halogenated formate esters, and (ii) methods using active intermediates obtained by reacting an alcohol with carbonyldiimidazole.

(i) Method using halogenated formate ester:
The target compound can be produced by reacting the starting compound with a halogenated formate in a reaction solvent in the presence of a basic compound.

  As a reaction solvent which can be used here, a solvent which does not inhibit the reaction can be widely used. Such solvents include, for example, aprotic polar solvents such as DMSO and acetonitrile, hydrocarbon solvents such as benzene, toluene, xylene, tetralin and liquid paraffin, and halogenated hydrocarbons such as methylene chloride, chloroform and dichloroethane. Examples thereof include solvents, ether solvents such as THF, dioxane, dipropyl ether, diethyl ether and diglyme, acetone, ethyl acetate, and the above mixed solvents.

  A wide variety of known basic compounds can be used as the basic compound, and examples thereof include inorganic basic compounds such as hydroxides, carbonates and hydrogencarbonates, and organic basic compounds such as acetates.

  Specific examples of the hydroxide include sodium hydroxide, potassium hydroxide, cesium hydroxide, lithium hydroxide and the like. Specific examples of the carbonate include sodium carbonate, potassium carbonate, cesium carbonate, lithium carbonate and the like. Specific examples of the hydrogen carbonate include sodium hydrogencarbonate, potassium hydrogencarbonate, cesium hydrogencarbonate, lithium hydrogencarbonate and the like.

  Specific examples of the acetate include sodium acetate, potassium acetate and the like. Specific examples of organic basic compounds other than the above include triethylamine, trimethylamine, diisopropylethylamine, pyridine, dimethylaniline, 1-methylpyrrolidine, N-methylmorpholine, DBN, DBU, DABCO and the like.

  Such a basic compound is generally used in an equimolar to 4 times molar amount, preferably 1 to 1.5 times molar, more preferably 1 to 1.1 times molar, relative to the starting compound.

  The halogenated formic acid ester is used in an equimolar to excess molar amount, preferably equimolar to 1.5 times molar, more preferably equimolar to 1.1 times molar, relative to the starting compound.

  The reaction temperature is generally 0-100 ° C., preferably 0-60 ° C., more preferably 10-30 ° C. The reaction time is usually 30 minutes to 12 hours, preferably 1 to 6 hours, more preferably 1 to 2 hours.

(ii) Method of using an active intermediate:
In a suitable solvent, an alcohol represented by the general formula R ²⁷ OH (where R ²⁷ is the same as above) is reacted with 1,1′-carbonyldiimidazole to obtain an active intermediate (first step), then obtained The target compound can be produced by reacting the starting compound with the active intermediate (step 2).

  As a reaction solvent which can be used here, a solvent which does not inhibit the reaction can be widely used. As such solvent, for example, aprotic polar solvents such as DMF, DMSO and acetonitrile, hydrocarbon solvents such as benzene, toluene, xylene, tetralin and liquid paraffin, halogenated carbons such as methylene chloride, chloroform and dichloroethane Examples thereof include hydrogen solvents, ether solvents such as THF, dioxane, dipropyl ether, diethyl ether, diglyme and the like, acetone, ethyl acetate, and the above mixed solvents and the like.

  1,1'-Carbonyldiimidazole is usually equimolar to excess molar, preferably equimolar to 1.5 times molar, more preferably equimolar to 1.1 times the alcohol represented by the above general formula It is good to use a mole.

  The reaction temperature of the first step is usually 0-100 ° C., preferably 0-60 ° C., more preferably 10-30 ° C. The reaction time is usually 30 minutes to 12 hours, preferably 1 to 6 hours, more preferably 1 to 2 hours.

  The active intermediate may be used in an equimolar to excess molar amount, preferably equimolar to 1.5 times molar, more preferably equimolar to 1.1 times molar, relative to the starting compound.

  The reaction temperature in the second step is usually 0-100 ° C, preferably 0-60 ° C, more preferably 10-30 ° C. The reaction time is usually 30 minutes to 12 hours, preferably 1 to 6 hours, more preferably 1 to 2 hours.

  For example, after cooling the reaction mixture obtained by the above method (i) or (ii), the crude reaction product is separated by an isolation operation such as filtration, concentration, extraction, etc., column chromatography, recrystallization etc. The desired carbamate compound can be isolated and purified from the reaction mixture by the usual purification procedure of

The compound of the present invention of the general formula (1) has a heterocycle containing a nitrogen atom in the molecule, and the nitrogen atom on the heterocycle has a R ³² R ³³ NCO- (R ³² and R ³³ are as defined above) group The compound in which is substituted is prepared by ureazing a compound in which a nitrogen atom on the corresponding heterocycle is substituted by a hydrogen atom.

In this ureazation reaction, for example, (i) a method using an amine represented by the general formula R ³² R ³³ NH (wherein R ³² and R ³³ are the same as above) and triphosgene, (ii) a general formula R ^A reaction using an amine represented by ³² R ³³ NH (wherein R ³² and R ³³ are the same as above) and carbonyldiimidazole, a method using (iii) an isocyanate compound, and the like can be applied.

  The reaction of (i), (ii) and (iii) is, for example, the same reaction as the reaction of (i), (ii) and (iii) described in the carbamate formation of the compound (1-A-A1) above. Performed under conditions.

  For example, after cooling the reaction mixture obtained by the method of the above (i), (ii) or (iii), the crude reaction product is separated by an isolation operation such as filtration, concentration, extraction and the like, and column chromatography The desired compound can be isolated and purified from the reaction mixture by ordinary purification procedures such as recrystallization and the like.

The compound of the present invention of the general formula (1) has a heterocycle containing a nitrogen atom in the molecule, and the nitrogen atom on the heterocycle contains a group R ^38a- (R ^38a is a C1-6 alkanoyl group, phenyl C2 6 alkanoyl group (in which at least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group is substituted on the phenyl ring Phenoxy C 2-6 alkanoyl group which may have a halogen atom substituted on the phenyl ring, phenylthio C 2-6 alkanoyl group which may have a halogen atom substituted on the phenyl ring, benzoyl group On the phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group, a halogen-substituted or unsubstituted C1-6 alkoxy And at least one of a group selected from the group consisting of C.sub.1-6 alkylamino groups may be substituted), a 4-biphenylylcarbonyl group, a pyridylcarbonyl group or a halogen atom is substituted on the phenyl ring, Compounds in which a good phenyl C2-6 alkenylcarbonyl group is substituted) are compounds represented by the general formula R ^38a OH (R ^38a is the same as above) to a compound in which a nitrogen atom on the corresponding heterocycle is substituted by a hydrogen atom. It is produced by reacting the carboxylic acid.

  This reaction is carried out under the same reaction conditions as the reaction of compound (Ea-2) with compound (18) in the following reaction scheme-19.

  The reaction mixture obtained by the above method is, for example, cooled, and then the crude reaction product is separated by an isolation operation such as filtration, concentration, extraction and the like, and by a usual purification operation such as column chromatography and recrystallization, The desired compound can be isolated and purified from the reaction mixture.

In the compound of the present invention of the general formula (1), the molecule has a heterocycle containing a nitrogen atom in the molecule, and the nitrogen atom on the heterocycle contains a group R ^39a SO _2- (R ^39a is a halogen atom and a C1-6 alkyl group And a compound in which a nitrogen atom on the corresponding heterocycle is substituted with a hydrogen atom, the compound having the general formula R ^39a SO 2 is a compound in which at least one selected from the group consisting of It is produced by reacting a sulfonic acid halide represented by ₂ X ² (R ^39a and X ² are as defined above).

  This reaction is carried out under the same reaction conditions as the reaction of compound (Fd-1) with compound (15) in the following reaction scheme-18.

  The reaction mixture obtained by the above method is, for example, cooled, and then the crude reaction product is separated by an isolation operation such as filtration, concentration, extraction and the like, and by a usual purification operation such as column chromatography and recrystallization, The desired compound can be isolated and purified from the reaction mixture.

The compound of the present invention of the general formula (1) has a heterocycle containing a nitrogen atom in the molecule, and the nitrogen atom on the heterocycle contains a group R ^40a R ⁵² CH- (where R ^40a is a phenyl group [phenyl ring Are a halogen atom, a cyano group, a halogen substituted or unsubstituted C1-6 alkyl group, a cyclohexyl group, an amino group which may have a C1-6 alkyl group as a substituent, a C1-6 alkoxycarbonyl group, a phenoxy At least one member selected from the group consisting of a group, phenyl C1-6 alkyl group, phenyl C2-6 alkenyl group, pyridyl group, imidazolyl group, halogen-substituted or unsubstituted C1-6 alkoxy group and piperidinyl group is substituted [4] a biphenylyl group [on the phenyl ring, a halogen atom, a cyano group, a halogen-substituted or unsubstituted C1-6 alkyl group And at least one member selected from the group consisting of halogen-substituted or unsubstituted C1-6 alkoxy groups and amino groups optionally having a C1-6 alkyl group as a substituent may be substituted], naphthyl Group, a furyl group or a thienyl group, wherein R ⁵² represents a hydrogen atom or a C1-6 alkyl group), reduces a compound in which a nitrogen atom on the corresponding heterocycle is substituted with a hydrogen atom, Manufactured by subjecting to a selective alkylation reaction.

This reductive alkylation reaction is carried out, for example, by using an aldehyde or ketone represented by the general formula R ⁴⁰ R ⁵² CO (R ⁴⁰ and R ⁵² are the same as above) to the starting compound in the presence of a reducing agent in a suitable solvent. Reaction is carried out.

  This reaction is carried out under the same reaction conditions as the reaction of compound (E-2) with compound (13) in the following reaction scheme-16.

  The reaction mixture obtained by the above method is, for example, cooled, and then the crude reaction product is separated by an isolation operation such as filtration, concentration, extraction and the like, and by a usual purification operation such as column chromatography and recrystallization, The desired compound can be isolated and purified from the reaction mixture.

[Wherein, R ^1a , X ² and n are as defined above. R ^24a represents a group represented by (Fca1) to (Fca11). R ^42a represents a C1-6 alkyl group. R ⁴² represents a group represented by (Fca5), (Fca6) or (Fca7). R ^42c represents a group represented by (Fca2), (Fca3), (Fca4), (Fca8) or (Fca9). R ^42b represents a phenyl group (in which at least one halogen-substituted or unsubstituted C1-6 alkyl group may be substituted on the phenyl ring). ]
The reaction for converting the compound (1-F-Fc16a) to the compound (1-F-Fc16b) is the same reaction condition as the reaction for converting the compound (E-1) to the compound (E-2) in the following Reaction scheme 16 It takes place below.

  The reaction mixture thus obtained can be concentrated, and if necessary, it can be crystallized by adding an acid such as hydrochloric acid, and the target compound in the form of hydrochloride or trifluoroacetate can be isolated by recrystallization or the like.

Compound (1-F-Fc16c) is produced by reacting compound (1-F-Fc16b) with a halide represented by the general formula R ^42c X ² .

  This reaction is carried out under the same reaction conditions as the reaction of compound (Ed-1) with compound (15) in the following reaction scheme-18.

Compound (1-F-Fc16d) is produced by reacting compound (1-F-Fc16b) with a carboxylic acid represented by the general formula R ⁴² OH.

  This reaction is carried out under the same reaction conditions as the reaction of compound (Ea-2) with compound (18) in the following reaction scheme-19.

  The reaction mixture obtained by the above method is, for example, cooled, and then the crude reaction product is separated by an isolation operation such as filtration, concentration, extraction and the like, and by a usual purification operation such as column chromatography and recrystallization, The desired compound can be isolated and purified from the reaction mixture.

Compound (1-F-Fc16e) is produced by reacting compound (1-F-Fc16b) with an isocyanate compound represented by the general formula R ^42b NCO.

  The reaction of the compound (1-F-Fc 16b) with the isocyanate compound is carried out in the presence or absence of a basic compound, preferably in the absence of a suitable inert solvent or in the absence of a solvent.

  Examples of basic compounds include triethylamine, trimethylamine, pyridine, dimethylaniline, N-ethyldiisopropylamine, dimethylaminopyridine, N-methylmorpholine, 1,5-diazabicyclo [4.3.0] nonene-5 (DBN). Organic bases such as 1,8-diazabicyclo [5.4.0] undecene-7 (DBU), 1,4-diazabicyclo [2.2.2] octane (DABCO), sodium carbonate, potassium carbonate, sodium hydrogen carbonate Carbonates such as potassium hydrogen carbonate, metal hydroxides such as sodium hydroxide, potassium hydroxide and calcium hydroxide, potassium hydride, sodium hydride, potassium, sodium, sodium amide, sodium methylate, sodium ethylate, etc. Inorganic bases such as metal alcoholates of It is. Further, as the solvent, for example, halogenated hydrocarbons such as chloroform, dichloromethane, dichloroethane, carbon tetrachloride, aromatic hydrocarbons such as benzene, toluene, xylene and the like, diethyl ether, diisopropyl ether, tetrahydrofuran, dimethoxyethane and the like Aprotic polar solvents such as ethers, esters such as methyl acetate, ethyl acetate and isopropyl acetate, N, N-dimethylacetamide, N, N-dimethylformamide, dimethylsulfoxide and hexamethylphosphoric acid triamide, methanol, ethanol, Alcohols such as isopropanol, propanol, butanol, 3-methoxy-1-butanol, ethyl cellosolve, methyl cellosolve, acetonitrile, pyridine, acetone, water, etc. or mixed solvents thereof

  The amount of the isocyanate compound used is usually about 1 to 5 times by mole, preferably 1 to 3 times by mole, relative to the compound (1-F-Fc 16b). The reaction is carried out usually at a temperature of about 0 to 200 ° C., preferably at about room temperature to about 150 ° C., usually for about 5 minutes to 30 hours.

  A boron compound such as boron trifluoride diethyl ether complex or a copper halide compound such as cuprous chloride may be added to the reaction system of the reaction.

  The reaction mixture thus obtained is, for example, cooled, and then the crude reaction product is separated by an isolation operation such as filtration, concentration, extraction and the like, and the objective is obtained by a usual purification operation such as column chromatography and recrystallization. The compounds can be isolated and purified from the reaction mixture.

[Wherein, R ^1a , R ^42a and n are as defined above. ]
Compound (1-Fdb) is produced by deprotecting compound (1-Fda). Specifically, for example, compound (1-Fdb) can be obtained by dissolving compound (1-Fda) in a suitable reaction solvent and hydrolyzing using an acid.

  As a reaction solvent which can be used here, a solvent which does not inhibit the reaction can be widely used. Examples of such solvents include water, alcohol solvents such as methanol and ethanol, aprotic polar solvents such as DMSO and acetonitrile, hydrocarbon solvents such as benzene, toluene, xylene, tetralin and liquid paraffin, methylene chloride Examples thereof include halogenated hydrocarbon solvents such as chloroform and dichloroethane, ether solvents such as THF, dioxane, dipropyl ether, diethyl ether and diglyme, acetone, ethyl acetate, and the above mixed solvents.

  Examples of the acid include inorganic acids such as hydrochloric acid, hydrobromic acid and bromic acid, and organic acids such as trifluoroacetic acid, trichloroacetic acid and acetic acid. Among these, trifluoroacetic acid is preferably used.

  The amount of these acids used is usually at least equimolar, preferably 2 to 10 times the molar amount of the compound (1-Fda), but these acids may be used in a large excess as a reaction solvent. The reaction temperature is usually room temperature to 100 ° C., but may be appropriately adjusted depending on the type of acid used. If trifluoroacetic acid is used, room temperature is sufficient. The reaction time is usually 1 to 24 hours, preferably 1 to 12 hours.

  The reaction mixture thus obtained is concentrated, and if necessary, it is crystallized by addition of an acid such as hydrochloric acid, and the compound (1-Fdb) in the form of hydrochloride or trifluoroacetate is isolated by recrystallization etc. it can.

[Wherein, R ^1a , R ^42a , n, R ³⁴ and R ³⁵ are as defined above. ]
Compound (1-Fdc) is produced by reacting compound (1-Fda) with an aldehyde or ketone represented by the general formula R ³⁴ COR ³⁵ (R ³⁴ and R ³⁵ are as defined above).

  This reaction is carried out in a suitable solvent in the presence of an acid.

  As a reaction solvent which can be used here, a solvent which does not inhibit the reaction can be widely used. Examples of such solvents include water, alcohol solvents such as methanol and ethanol, aprotic polar solvents such as DMSO and acetonitrile, hydrocarbon solvents such as benzene, toluene, xylene, tetralin and liquid paraffin, methylene chloride Examples thereof include halogenated hydrocarbon solvents such as chloroform and dichloroethane, ether solvents such as THF, dioxane, dipropyl ether, diethyl ether and diglyme, acetone, ethyl acetate, and the above mixed solvents.

  Examples of the acid include inorganic acids such as hydrochloric acid, hydrobromic acid and bromic acid, and organic acids such as trifluoroacetic acid, trichloroacetic acid and acetic acid. Among these, trifluoroacetic acid is preferably used.

  The amount of these acids used is usually at least 0.5 times mol, preferably 0.5 to 1.5 times mol, of the compound (1-Fda), but these acids are used in large excess as a reaction solvent It may be used for

  The amount of the aldehyde or ketone to be used is generally 0.9 to 3 times mol, preferably 1 to 1.5 times mol, more preferably 1 to 1.3 times mol, of the compound (1-Fda).

  The reaction temperature is usually room temperature to 100 ° C., but may be appropriately adjusted depending on the type of acid used. The reaction time is usually 1 to 12 hours, preferably 1 to 3 hours.

  The reaction mixture thus obtained is concentrated, and if necessary, it is crystallized by addition of an acid such as hydrochloric acid, and the compound (1-Fdc) in the form of hydrochloride or trifluoroacetate is isolated by recrystallization etc. it can.

  Next, methods for producing starting materials and intermediates for producing the compound of the present invention will be described.

[Wherein, R ^1a , R ⁷ , R ⁸ , X ¹ and n are as defined above. R ^3c represents a C1-6 alkoxy-C1-6 alkyl group, a C1-6 alkanoyl group or a p-nitrobenzoyl group. ]
The reaction leading to the compound (4e) from the compound (4d) leads, for example, to the compound (1-A-A1) from the compound (1-A-A3) or the compound (1-A-A9) in the reaction scheme-4. It is carried out under the same reaction conditions as the reaction. For example, in the case of a compound (4d) in which R ^3c represents a C1-6 alkoxy-C1-6 alkyl group, a reaction similar to the reaction leading to a compound (1-A-A1) from the compound (1-A-A3) may be carried out under the conditions, in the case of compounds exhibiting R ^3c is C1~6 alkanoyl group or p- nitrobenzoyl group (4d), the compound from the compound (1-a-A9) ( 1-a-A1 It is good to carry out under the same reaction conditions as the reaction leading to).

  The reaction for converting Compound (4e) to Compound (4f) is carried out, for example, under the same reaction conditions as the reaction for converting Compound (1-A-A1) to Compound (1-D) in Reaction scheme-7. .

[Wherein, R ^1a , R ^2a , R ^3a , X ¹ and n are as defined above. ]
The reaction for converting Compound (4e) to Compound (4g) is carried out, for example, under the same reaction conditions as the reaction for converting Compound (1-A-A1) to Compound (1-A-A7) in the reaction scheme-5. To be done.

  The reaction for converting compound (4g) to compound (4h) is performed, for example, under the same reaction conditions as the reaction for converting compound (1-A-A7) to compound (1b) in the reaction scheme-6.

[Wherein, R ^1a and X ¹ are as defined above. R ^2e represents a halogen atom, a C1-6 alkylsulfonyloxy group or a phenylsulfonyloxy group which may be substituted by a C1-6 alkyl group on the phenyl ring. ]
The reaction for converting compound (41) to compound (3b) is carried out in a suitable solvent in the presence of a basic compound.

  As a solvent that can be used here, a wide range of solvents that do not inhibit the reaction can be used. Such solvents include, for example, aprotic polar solvents such as DMSO and acetonitrile, hydrocarbon solvents such as benzene, toluene, xylene, tetralin and liquid paraffin, and halogenated hydrocarbons such as methylene chloride, chloroform and dichloroethane. Examples thereof include solvents, ether solvents such as THF, dioxane, dipropyl ether, diethyl ether and diglyme, acetone, ethyl acetate, and the above mixed solvents.

  As the basic compound, the same basic compounds as those used in the reaction of the compound of the above general formula (2) with the compound of the general formula (3a) can be used.

  The basic compound is generally used in an equimolar to excess molar amount, preferably 1 to 5 times molar, more preferably 1 to 2 times molar, relative to compound (4l).

  The reaction temperature of this reaction is usually 0 to 150 ° C., preferably 0 to 100 ° C., more preferably 0 to 60 ° C. The reaction time is usually 30 minutes to 48 hours, preferably 1 to 24 hours, more preferably 1 to 4 hours.

  The reaction mixture obtained by the above method is, for example, cooled, and then the crude reaction product is separated by an isolation operation such as filtration, concentration, extraction and the like, and by a usual purification operation such as column chromatography and recrystallization, Compound (3b) can be isolated and purified from the reaction mixture.

[Wherein, R ¹ , R ² and n are as defined above. ]
The reaction for converting Compound (5) to Compound (3f) is carried out, for example, by treating Compound (5) with trimethylsulfoxonium iodide in the presence of a basic compound in a suitable solvent.

  As a solvent that can be used here, a wide range of solvents that do not inhibit the reaction can be used. As such solvent, for example, aprotic polar solvents such as DMSO and acetonitrile, hydrocarbon solvents such as benzene, toluene, xylene, tetralin and liquid paraffin, THF, dioxane, dipropyl ether, diethyl ether, diglyme etc And the above-mentioned mixed solvents and the like.

  Examples of the basic compound include metal hydrides such as sodium hydride, sodium amide, sodium methoxide, sodium ethoxide, potassium tert-butoxide and the like.

  These basic compounds are generally used in an equimolar to excess molar amount, preferably 1 to 3 times molar, more preferably 1 to 1.5 times molar relative to the compound (5).

  The trimethylsulfoxonium iodide is generally used in an equimolar to excess molar amount, preferably 1 to 3 times the molar amount, more preferably 1 to 1.5 times the molar amount, relative to the compound (5).

  The reaction temperature of this reaction is usually 0 to 80 ° C, preferably 10 to 50 ° C, more preferably 20 to 35 ° C. The reaction time is usually 1 to 24 hours, preferably 1 to 12 hours, more preferably 1 to 4 hours.

  The reaction mixture obtained by the above method is, for example, cooled, and then the crude reaction product is separated by an isolation operation such as filtration, concentration, extraction and the like, and by a usual purification operation such as column chromatography and recrystallization, Compound (3f) can be isolated and purified from the reaction mixture.

  The reaction for converting Compound (6) to Compound (3f) is carried out, for example, by treating Compound (6) with a peroxide in a suitable solvent.

  As a reaction solvent which can be used here, a solvent which does not inhibit the reaction can be widely used. As such solvent, for example, alcohol solvents such as water, methanol and ethanol, aprotic polar solvents such as DMF, DMSO and acetonitrile, hydrocarbons such as benzene, toluene, xylene, tetralin, liquid paraffin and cyclohexane Examples thereof include solvents, halogenated hydrocarbon solvents such as methylene chloride, chloroform and dichloroethane, ether solvents such as THF, dioxane, dipropyl ether, diethyl ether and diglyme, and the above mixed solvents.

  Examples of the peroxide include metachloroperbenzoic acid (mCPBA), perbenzoic acid, peracetic acid, hydrogen peroxide and the like.

  These peroxides may be used in an amount of usually 1 to 2 moles, preferably 1 to 1.5 moles, more preferably 1 to 1.3 moles per mole of the compound (6).

  The reaction temperature of this reaction is usually 0 to 80 ° C, preferably 0 to 50 ° C, more preferably 20 to 35 ° C. The reaction time is usually 10 minutes to 24 hours, preferably 1 to 12 hours, more preferably 1 to 8 hours.

  The reaction mixture obtained by the above method is, for example, cooled, and then the crude reaction product is separated by an isolation operation such as filtration, concentration, extraction and the like, and by a usual purification operation such as column chromatography and recrystallization, Compound (3f) can be isolated and purified from the reaction mixture.

  The optically active compound (3f) is produced, for example, from compound (6) as follows.

The optically active compound (3f) is prepared by using cumene hydroperoxide or tert-butyl hydroperoxide in place of the peroxide in the reaction for converting the compound (6) to the compound (3f) and using Ti (O-iso-) as a catalyst C ₃ H _{7) 4} and oxidized in the presence of tartaric acid C1~6 alkyl esters such as optically active tartaric acid diethyl (D or L- form), it can be prepared by the so-called Sharpless epoxidation.

  As a solvent used for this reaction, a solvent which does not inhibit this reaction can be widely used. Such solvents include, for example, aprotic polar solvents such as acetonitrile, hydrocarbon solvents such as benzene, toluene, xylene, tetralin, liquid paraffin and cyclohexane, halogenated hydrocarbons such as methylene chloride, chloroform and dichloroethane Examples thereof include solvents, ether solvents such as THF, dioxane, dipropyl ether, diethyl ether and diglyme, and mixed solvents thereof.

  The cumene hydroperoxide or tert-butyl hydroperoxide is generally 0.1 to 2 times mol, preferably 0.1 to 1.5 times mol, more preferably 0.1 times to 1 mol of the compound (6). You may use a mole.

Ti (O-iso-C ₃ H ₇ ) ₄ is generally 0.1 to 2 times mol, preferably 0.1 to 1.5 times mol, more preferably 0.1 times the amount of the compound (6) Mole to equimolar may be used.

  The optically active tartaric acid C1-6 alkyl ester (D or L-form) is generally equimolar to 2-fold molar, preferably equimolar to 1.5-fold molar, more preferably equimolar to the compound (6) It is sufficient to use a mole of ~ 1.3-fold.

  The reaction temperature of this reaction is usually -50 to 30 ° C, preferably -20 to 20 ° C, more preferably -20 to 5 ° C. The reaction time is usually 1 to 48 hours, preferably 4 to 24 hours, more preferably 4 to 12 hours.

In the compound (5) or the compound (6), when R ¹ and-(CH ₂ ) _n R ^2a are bonded to each other via a nitrogen atom together with the adjacent carbon atom to form a piperidine ring, the above Compounds (3f) in which R ¹ and-(CH ₂ ) _n R ^2a are bonded to each other through the nitrogen atom together with the adjacent carbon atom to form a piperidine ring (compound (3c) Can lead to)).

  The reaction mixture obtained by the above method is, for example, cooled, and then the crude reaction product is separated by an isolation operation such as filtration, concentration, extraction and the like, and by a usual purification operation such as column chromatography and recrystallization, The optically active compound (3f) can be isolated and purified from the reaction mixture.

  The compound (final compound) represented by the general formula (1) of the present invention and the intermediates obtained in the above reaction schemes include stereoisomers and optical isomers.

[Wherein, R ^1a , R ^2a , R ^3a and n are as defined above. ]
The reaction for converting the compound (3g) to the compound (3h) is performed, for example, under the same reaction conditions as the reaction for converting the compound (1-A-A7) to the compound (1b) in the reaction scheme-6.

[Wherein, R ^1a , X, n and m are as defined above. R ^11a is a group

(W and o are the same as above. R ^15a represents a C1-20 alkoxycarbonyl group, provided that when W represents a group C = O, R ^15a represents a C1-6 alkoxycarbonyl group. ) Or groups

(R ^16a represents a C1-8 alkoxycarbonyl group). R ^11b is a group

(W and o are the same as above.)
Or group

Indicates R ^11c is a group

(R ^15b represents a C3-8 cycloalkyl group) or a group

(R ^16b represents a C3-8 cycloalkyl group). R ^A represents a C3-8 cycloalkyl group. ]
Compound (E-2) is produced by hydrolyzing compound (E-1).

  This hydrolysis reaction is carried out in a suitable solvent or without solvent, in the presence of an acid or a basic compound.

  As the solvent to be used, for example, lower alcohols such as water, methanol, ethanol, isopropanol and tert-butanol, ketones such as acetone and methyl ethyl ketone, ethers such as diethyl ether, dioxane, tetrahydrofuran, monoglyme and diglyme, acetic acid, Fatty acids such as formic acid, esters such as methyl acetate and ethyl acetate, halogenated hydrocarbons such as chloroform, dichloromethane, dichloroethane and carbon tetrachloride, dimethyl sulfoxide, N, N-dimethylformamide, hexamethyl phosphate triamide or a mixture thereof A solvent etc. can be mentioned.

  Examples of the acid include mineral acids such as hydrochloric acid, sulfuric acid and hydrobromic acid; and organic acids such as sulfonic acids such as formic acid, acetic acid, trifluoroacetic acid and p-toluenesulfonic acid.

  Examples of the basic compound include carbonates such as sodium carbonate, potassium carbonate, sodium hydrogencarbonate and potassium hydrogencarbonate, and metal hydroxides such as sodium hydroxide, potassium hydroxide, calcium hydroxide and lithium hydroxide. be able to.

  The reaction suitably proceeds usually at about 0 to 200 ° C., preferably at about 0 to 150 ° C., and is generally completed in about 10 minutes to 30 hours.

  The amount of the acid or basic compound used is at least equimolar, preferably equimolar to 10 molar, per 1 mole of the compound (E-1), but may be used in a large excess as a reaction solvent.

  After the above hydrolysis treatment, in order to complete the reaction, the above hydrolysis reaction solution is usually prepared in the presence of a basic compound in a suitable solvent at 0 to 100 ° C., preferably at room temperature to 70 ° C. You may hold for about 30 minutes. Examples of basic compounds include triethylamine, trimethylamine, pyridine, dimethylaniline, N-ethyldiisopropylamine, dimethylaminopyridine, N-methylmorpholine, 1,5-diazabicyclo [4.3.0] nonene-5 (DBN). Organic bases such as 1,8-diazabicyclo [5.4.0] undecene-7 (DBU), 1,4-diazabicyclo [2.2.2] octane (DABCO), sodium carbonate, potassium carbonate, sodium hydrogen carbonate Carbonates such as potassium hydrogen carbonate, metal hydroxides such as sodium hydroxide, potassium hydroxide and calcium hydroxide, potassium hydride, sodium hydride, potassium, sodium, sodium amide, sodium methylate, sodium ethylate, etc. Inorganic bases such as metal alcoholates of It is. Further, as the solvent, for example, halogenated hydrocarbons such as chloroform, dichloromethane, dichloroethane, carbon tetrachloride, aromatic hydrocarbons such as benzene, toluene, xylene and the like, diethyl ether, diisopropyl ether, tetrahydrofuran, dimethoxyethane and the like Aprotic polar solvents such as ethers, esters such as methyl acetate, ethyl acetate and isopropyl acetate, N, N-dimethylacetamide, N, N-dimethylformamide, dimethylsulfoxide and hexamethylphosphoric acid triamide, methanol, ethanol, Alcohols such as isopropanol, propanol, butanol, 3-methoxy-1-butanol, ethyl cellosolve, methyl cellosolve, acetonitrile, pyridine, acetone, water, etc. or mixed solvents thereof

  The reaction of compound (E-2) with compound (13) is carried out without solvent or in a suitable solvent in the presence of a reducing agent.

  Examples of the solvent to be used herein include lower alcohols such as water, methanol, ethanol, isopropanol, butanol, tert-butanol, ethylene glycol, etc., fatty acids such as acetonitrile, formic acid, acetic acid, trifluoroacetic acid, diethyl ether, tetrahydrofuran And ethers such as dioxane, monoglyme and diglyme, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and mixed solvents thereof.

  As the reducing agent, for example, a fatty acid alkali metal salt such as formic acid, sodium formate and sodium acetate, sodium borohydride sodium, sodium cyanoborohydride, sodium triacetyloxyborohydride hydride, and a hydrogenation reducing agent such as lithium aluminum hydride Or the mixture of these hydrogenation reducing agents, catalytic hydrogen reducing agents, such as palladium black, palladium carbon, platinum oxide, platinum black, Raney nickel, etc. can be illustrated.

  When formic acid is used as the reducing agent, the reaction temperature is usually about room temperature to 200 ° C., preferably about 50 to 150 ° C., and the reaction is completed in about 10 minutes to 10 hours. Formic acid is preferably used in a large excess relative to compound (E-2).

  When a hydrogenation reducing agent is used as the reducing agent, the reaction temperature is usually about −80 to 100 ° C., preferably about −80 to 70 ° C., and the reaction is completed in about 30 minutes to 100 hours. The amount of the hydrogenation reducing agent to be used is generally equimolar to 20 times molar amount, preferably equimolar to 6 times molar, with respect to compound (E-2). In particular, when lithium aluminum hydride is used as the reducing agent, it is preferable to use, as a solvent, ethers such as diethyl ether, tetrahydrofuran, dioxane, monoglyme and diglyme, and aromatic hydrocarbons such as benzene, toluene and xylene.

  In the reaction system of this reaction, amines such as trimethylamine, triethylamine and N-ethyldiisopropylamine may be added, and molecular sieves 3A (MS-3A), molecular sieves 4A (MS-4A), etc. Molecular sieves may be added.

  Furthermore, when using a catalytic hydrogen reducing agent, a hydrogen donor such as formic acid, ammonium formate, cyclohexene, hydrazine hydrate, etc., usually in a hydrogen atmosphere of about normal pressure to about 20 atm, preferably about normal pressure to about 10 atm. The reaction is preferably carried out at a temperature of about -30 to 100 ° C, preferably about 0 to 60 ° C, in the presence of H. The reaction is usually completed in about 1 to 12 hours. The amount of the catalytic hydrogen reducing agent used is usually about 0.1 to 40% by weight, preferably about 1 to 20% by weight, relative to the compound (E-2).

  The amount of compound (13) to be used is generally at least an equimolar amount, preferably an equimolar to large excess amount, relative to compound (E-2).

[Wherein, R ^1a , X, n, m, W and o are the same as above]. R ^14Aa represents a hydrogen atom, a hydroxyl group, a C1-6 alkoxy group or a phenyl group (a halogen atom may be substituted on the phenyl ring). R ^{14 b} represents a C1-6 alkoxycarbonyl group. ]
The reaction for converting the compound (Eaa6-1) to the compound (Eaa5-1) is carried out under the same reaction conditions as the reaction for converting the compound (E-1) to the compound (E-2) in the aforementioned Reaction scheme-16. .

[Wherein, R ^1a , n, R ⁵² and X ² are as defined above.
R ^{26 b} is a halogen atom, a cyano group, an amino group which may have a C1-6 alkyl group as a substituent, a halogen substituted or unsubstituted C1-6 alkyl group, a halogen substituted or unsubstituted C1-6 alkoxy group, Selected from the group consisting of a C1-6 alkoxycarbonyl group, a carboxyl group, a phenoxy group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group At least one of the above-mentioned groups may be substituted), an amino C1-6 alkyl group (on the amino group, a C1 to 6 alkyl group and a phenyl group [on the phenyl ring, a halogen atom, halogen substitution or At least a group selected from the group consisting of unsubstituted C1-6 alkyl groups and halogen substituted or unsubstituted C1-6 alkoxy groups Or at least one group selected from the group consisting of one group may be substituted) or a phenyl C1-6 alkoxy group (on the phenyl ring, a halogen atom, halogen substitution, Or at least one of a group selected from the group consisting of an unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted).
p shows the integer of 0-4.
R ^26a is a group -NHR ^26h (wherein R ^26h represents a hydrogen atom or a C1-6 alkyl group) or a group -W ₁ -NHR ^26c (wherein W ₁ is the same as above. R ^26c is a hydrogen atom, C1-6 alkyl Group or a phenyl group (on the phenyl ring, at least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group is May be substituted)).
R ^{26 d} represents a group —NR ^{26 e ′} R ^{26 h} or a group —W ₁ —NR ^{26 c} R ^{26 e} . R ^{26 e} is a phenyl group (on the phenyl ring, at least one of the groups selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group The species may be substituted) or C1-6 alkyl. R ^{26e ′} represents a C1-6 alkyl group.
R ^{26 f} represents a C1-6 alkyl group.
R ^{26 g} is a group ^{-N (R 26h) CHR 52 R} 26f or a group -W ₁ -N (R ^26c) shows a CHR ⁵² R ^26f. However the group ^{-N (R 26h) CHR 52 R} CHR 52 R 26f moiety and group -W ₁ -N in ^26f (R ^26c) CHR ⁵² the total number of carbon atoms of CHR ⁵² R ^26f moiety in R ^26f is not exceed 6 I assume. ]
The reaction of compound (Fd-1) with compound (15) is generally carried out in a suitable solvent, in the presence or absence of a basic compound.

  As an inert solvent to be used, for example, aromatic hydrocarbons such as benzene, toluene and xylene, ethers such as diethyl ether, tetrahydrofuran, dioxane, monoglyme and diglyme, halogens such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride Lower hydrocarbons such as methanol, ethanol, isopropanol, butanol, tert-butanol and ethylene glycol, fatty acids such as acetic acid, esters such as ethyl acetate and methyl acetate, ketones such as acetone and methyl ethyl ketone, acetonitrile, Pyridine, dimethylsulfoxide, N, N-dimethylformamide, hexamethylphosphoric acid triamide or a mixed solvent thereof can be mentioned.

  Examples of the basic compound include carbonates such as sodium carbonate, potassium carbonate, sodium hydrogencarbonate, potassium hydrogencarbonate and cesium carbonate, metal hydroxides such as sodium hydroxide, potassium hydroxide and calcium hydroxide, sodium hydride , Metal hydrides such as potassium hydride, potassium, sodium, sodium amide, sodium methylate, sodium ethylate, sodium n-butoxide, pyridine, imidazole, N-ethyldiisopropylamine, dimethylaminopyridine, triethylamine, trimethylamine, dimethylaniline , N-methylmorpholine, 1,5-diazabicyclo [4.3,0] nonene-5 (DBN), 1,8-diazabicyclo [5.4.0] undecene-7 (DBU), 1,4-diazabicyclo [5] 2.2. ] Can be exemplified organic bases or mixtures thereof, such as octane (DABCO).

  The compound (15) is generally used in an amount of at least equimolar amount, preferably about equimolar to 10 times molar amount, relative to the compound (Fd-1). In addition, the basic compound is generally used in an amount of at least equimolar amount, preferably about equimolar to 10-fold molar amount, relative to compound (Fd-1).

  This reaction is carried out generally at 0-200 ° C., preferably at about 0-150 ° C., and the reaction is completed generally in about 5 minutes to 80 hours.

  Into the reaction system of this reaction, an alkali metal halogen compound such as sodium iodide or potassium iodide may be added, or a phase transfer catalyst may be added.

  As a phase transfer catalyst, for example, tetrabutyl ammonium chloride, tetrabutyl ammonium bromide, tetrabutyl ammonium fluoride, tetrabutyl ammonium iodide, tetrabutyl ammonium hydroxide, tetrabutyl ammonium hydrogen sulfite, tributyl methyl ammonium chloride, tributyl benzyl ammonium Chloride, tetrapentyl ammonium chloride, tetrapentyl ammonium bromide, tetrahexyl ammonium chloride, benzyl dimethyl octyl ammonium chloride, methyl trihexyl ammonium chloride, benzyl dimethyl octadecanyl ammonium chloride, methyl tridecanyl ammonium chloride, benzyl tripropyl ammonium chloride, Benzyl tri It is selected from the group consisting of a linear or branched alkyl group having 1 to 18 carbon atoms such as ethyl ammonium chloride, phenyl triethyl ammonium chloride, tetraethyl ammonium chloride, tetramethyl ammonium chloride, phenyl C 1-6 alkyl group and phenyl group Carbon atoms such as 1-dodecanyl pyridinium chloride and the like, quaternary ammonium salts and the like having a substituted group, phosphonium salts and the like having 1 to 18 carbon atoms such as tetrabutylphosphonium chloride and the like, or linear or branched alkyl groups; The pyridinium salt etc. which 1-18 linear or branched alkyl group substituted can be illustrated.

  The phase transfer catalyst is generally used in an amount of 0.1 mol to 1 mol, preferably 0.1 to 0.5 mol, per mol of the compound (Fd-1).

  The reaction of compound (Fd-1) with compound (16) is carried out under the same reaction conditions as the reaction of compound (E-2) with compound (13) in the aforementioned Reaction scheme-16.

[Wherein, R ^1a , n, W, X, m, o, R ⁵² and X ² are as defined above.
R ^12a represents a C1-6 alkoxycarbonyl group.
R ^13a is a hydrogen atom, a C1-6 alkyl group, a C1-6 alkanoyl group, a C1-6 alkoxycarbonyl group, a phenyl C1-6 alkyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1 6 alkyl group, halogen substituted or unsubstituted C1-6 alkoxy group and phenoxy group [in the phenyl ring, halogen atom, halogen substituted or unsubstituted C1-6 alkyl group and halogen substituted or unsubstituted C1-6 alkoxy group At least one group selected from the group consisting of groups may be substituted], and at least one group selected from the group consisting of groups may be substituted. 6 alkoxyimino group may be substituted), phenyl group (on the phenyl ring, a halogen atom, halogen substituted or unsubstituted C1 to C6) At least one of a group selected from the group consisting of an alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group may be substituted, a benzoyl group (on the phenyl ring, a halogen atom, a halogen substitution or At least one of a group selected from the group consisting of an unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted), a pyridyl group (on a pyridine ring), At least one halogen atom may be substituted, phenoxy C1-6 alkyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1ベ ン ゾ イ ル 6 alkoxy group, at least one of the groups selected from the group consisting of may be substituted) or benzoyl C1-6 alkyl group (on the phenyl ring) , A halogen atom, at least one group selected from the group consisting of C1~6 alkoxy groups halogen-substituted or unsubstituted C1~6 alkyl group and a halogen substituted or unsubstituted may be substituted).
R ^12b is a C1-6 alkyl group, a C1-6 alkoxycarbonyl group, a phenyl C1-6 alkyl group (on the phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group, a halogen-substituted or an unsubstituted group A C 1-6 alkoxy group and a phenoxy group [in the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a group selected from the group consisting of a halogen substituted or unsubstituted C.sub.1-6 alkoxy group At least one group may be substituted], and at least one group selected from the group consisting of [1] may be substituted, and the alkyl moiety may be substituted by a C1-6 alkoxyimino group Phenyl group (on the phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted group. At least one group selected from the group consisting of a C1-6 alkoxy group may be substituted), pyridyl group (at least one halogen atom may be substituted on a pyridine ring), A phenoxy C.sub.1-6 alkyl group (on the phenyl ring, at least one of a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group; Or a benzoyl C.sub.1-6 alkyl group (on the phenyl ring, from a halogen atom, halogen substituted or unsubstituted C.sub.1-6 alkyl group and halogen substituted or unsubstituted C.sub.1-6 alkoxy group. At least one of the groups selected from the group consisting of
R ^12c is selected from the group consisting of a C1-6 alkanoyl group or a benzoyl group (on the phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group At least one of the above-mentioned groups may be substituted).
R ^12d is a hydrogen atom, a C1-6 alkyl group, a phenyl C1-6 alkyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group, a halogen substituted or unsubstituted C1-6 Alkoxy group and phenoxy group [in the phenyl ring, at least one of a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group And at least one group selected from the group consisting of (optionally substituted) may be substituted), a phenyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1 to C6) An alkyl group, a halogen substituted or unsubstituted C1-6 alkoxy group and a phenoxy group [on the phenyl ring, a halogen atom, a halogen substituted or At least one of a group selected from the group consisting of an unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group] may be substituted by at least one group selected from the group consisting of 1 type may be substituted, phenoxy C1-6 alkyl group (on the phenyl ring, halogen atom, halogen substituted or unsubstituted C1-6 alkyl group and halogen substituted or unsubstituted C1-6 alkoxy group Or at least one of a group selected from the group consisting of: or a benzoyl C1-6 alkyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen At least one group selected from the group consisting of a substituted or unsubstituted C.sub.1-6 alkoxy group may be substituted).
The total carbon number of the portion of CHR ⁵² R ^{12 d} constituting the group-(W) _o -N (R ^13a ) CHR ⁵² R ^{12 d} in the general formula (Ea-5) does not exceed 6. ]
The reaction for converting the compound (Ea-1) to the compound (Ea-2) is carried out under the same reaction conditions as the reaction for converting the compound (E-1) to the compound (E-2) in the aforementioned Reaction scheme-16. .

  The reaction of the compound (Ea-2) with the compound (17) is carried out under the same reaction conditions as the reaction of the compound (Ed-1) with the compound (15) in the aforementioned Reaction scheme-18.

  The reaction of compound (Ea-2) with carboxylic acid (18) is a common amide bond forming reaction. The conditions for known amide bond formation reaction can be easily used for the amide bond formation reaction. For example, (a) mixed acid anhydride method, ie, a method in which an alkyl halocarboxylic acid is reacted with carboxylic acid (18) to make a mixed acid anhydride and this is reacted with amine (Ea-2), (b) active ester The carboxylic acid (18) is an active ester such as phenyl, p-nitrophenyl ester, N-hydroxysuccinimide ester, 1-hydroxybenzotriazole ester, or an active amide with benzoxazoline-2-thione, (A) Carbodiimide method, ie, amine (Ea-2) with carboxylic acid (18), dicyclohexyl carbodiimide, 1- (3-dimethylaminopropyl) -3-ethyl carbodiimide ( A method of condensation reaction in the presence of an activator such as WSC), carbonyldiimidazole, etc. Other methods, for example, a method of converting carboxylic acid (18) into carboxylic acid anhydride with a dehydrating agent such as acetic anhydride and reacting it with amine (Ea-2), ester of carboxylic acid (18) with lower alcohol and amine Examples include a method of reacting (Ea-2) under high pressure and temperature, a method of reacting an amine (Ea-2) with an acid halide of carboxylic acid (18), that is, a carboxylic acid halide.

  The mixed acid anhydride used in the above mixed anhydride method (i) is obtained by a common Schotten-Baumann reaction, and is reacted with an amine (Ea-2) usually without isolation to obtain a general formula (Ea) The compound of the present invention is prepared.

  The Schotten-Baumann reaction is carried out in the presence of a basic compound. As the basic compound to be used, compounds conventionally used in Schotten-Baumann reaction, such as triethylamine, trimethylamine, pyridine, dimethylaniline, N-ethyldiisopropylamine, dimethylaminopyridine, N-methylmorpholine, 1,5-diazabicyclo [4] .3.0] Organic compounds such as nonene-5 (DBN), 1,8-diazabicyclo [5.4.0] undecene-7 (DBU), 1,4-diazabicyclo [2.2.2] octane (DABCO) Bases, carbonates such as sodium carbonate, potassium carbonate, sodium hydrogencarbonate and potassium hydrogencarbonate, metal hydroxides such as sodium hydroxide, potassium hydroxide and calcium hydroxide, potassium hydride, sodium hydride, sodium hydride, sodium, Sodium amide, sodium methylate, sodium Inorganic bases such as metal alcoholates such as Chirato like.

  The reaction is usually carried out at about -20 to 100 ° C, preferably about 0 to 50 ° C, and the reaction time is about 5 minutes to 10 hours, preferably about 5 minutes to 2 hours.

  The reaction of the obtained mixed acid anhydride with the amine (Ea-2) is carried out usually at about -20 to 150 ° C, preferably at about 10 to 50 ° C, and the reaction time is preferably about 5 minutes to 10 hours, Is about 5 minutes to 5 hours.

  The mixed acid anhydride method is generally carried out in a solvent. As the solvent to be used, any of the solvents commonly used in the mixed acid anhydride method can be used. Specifically, halogenated hydrocarbons such as chloroform, dichloromethane, dichloroethane, carbon tetrachloride, benzene, toluene, xylene Aromatic hydrocarbons such as diethyl ether, diisopropyl ether, tetrahydrofuran, ethers such as dimethoxyethane, esters such as methyl acetate, ethyl acetate, isopropyl acetate, N, N-dimethyl acetamide, N, N-dimethyl acetamide Aprotic polar solvents such as formamide, dimethylsulfoxide, hexamethylphosphoric acid triamide and the like, or mixed solvents thereof and the like can be mentioned.

  Examples of the alkyl halocarboxylic acid used in the mixed acid anhydride method include methyl chloroformate, methyl bromoformate, ethyl chloroformate, ethyl bromoformate, isobutyl chloroformate and the like. The proportions of carboxylic acid (18), alkyl halocarboxylic acid and amine (Ea-2) used in this method may be generally equimolar, but it is preferable to use alkyl halocarboxylic acid relative to amine (Ea-2). It is preferable to use carboxylic acid (18) in an equimolar to 1.5 times molar amount or so.

  In the method (3) of condensation reaction in the presence of the above-mentioned activating agent, the reaction is carried out in a suitable solvent, in the presence or absence of a basic compound. As the solvent and the basic compound used here, any of the solvents used in the method of reacting the amine halide (Ea-2) with the carboxylic acid halide of the method (ii) shown below can be used.

  The amount of the activating agent to be used is generally at least equimolar amount, preferably about equimolar to 5 times molar amount, relative to compound (Ea-2). When WSC is used as the activating agent, the reaction proceeds advantageously when 1-hydroxybenzotriazole is added to the reaction system. The reaction is usually carried out at about -20 to about 180 ° C, preferably at about 0 to 150 ° C, and the reaction is generally completed in about 5 minutes to about 90 hours.

  Moreover, when employ | adopting the method to which amine (Ea-2) is made to react with carboxylic acid halide among said method (ii), this reaction is performed in a suitable solvent in presence of a basic compound. A wide variety of known basic compounds can be used as the basic compound to be used, and, for example, any of the basic compounds used for the Schotten-Baumann reaction can be used. As the solvent, for example, in addition to the solvent used in the above mixed acid anhydride method, alcohols such as methanol, ethanol, isopropanol, propanol, butanol, 3-methoxy-1-butanol, ethyl cellosolve, methyl cellosolve, acetonitrile, Pyridine, acetone, water and the like can be mentioned.

  The proportions of the amine (Ea-2) and the carboxylic acid halide are not particularly limited and may be suitably selected within a wide range, but generally the latter is at least about equimolar, preferably equimolar to the former. It is preferable to use about 5 times molar amount.

  The reaction is usually carried out at about -20 to 180 ° C, preferably at about 0 to 150 ° C, and the reaction is generally completed in about 5 minutes to 50 hours.

  Furthermore, the above-mentioned amide bond formation reaction includes carboxylic acid (18) and amine (Ea-2), a condensing agent such as diphenyl phosphinic chloride, phenyl-N-fevir phosphoramide chloridate, diethyl chlorophosphate, cyano phosphorus The reaction is also carried out by the method of reacting in the presence of a phosphorus compound such as acid diethyl, diphenyl phosphate azide, bis (2-oxo-3-oxazolidinyl) phosphinic chloride and the like.

  The reaction is usually performed at about -20 to about 150 ° C, preferably at about 0 to about 100 ° C, in the presence of a solvent and a basic compound used in the method of reacting an amine (Ea-2) with the carboxylic acid halide. The reaction is generally completed in about 5 minutes to 30 hours. The condensing agent and the carboxylic acid (18) are used in an amount of at least about equimolar amount, preferably about equimolar to 2-fold molar amount, with respect to the amine (Ea-2).

  The reaction of compound (Ea-2) with compound (19) is carried out under the same reaction conditions as the reaction of compound (E-2) with compound (13) in the aforementioned Reaction scheme-16.

[Wherein, R ^1a , n, R ⁵² , p and X ² are the same as above].
R ^19a represents the same group as the group represented by the above-mentioned F1) to F11).
R ⁵³ is a phenoxy group (on the phenyl ring, at least one of a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group Species may be substituted), a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group, a halogen substituted or unsubstituted C1-6 alkoxy group, a C1-6 alkyl group as a substituent and a phenyl C1-6 An alkyl group (on the phenyl ring, at least one of a group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group, and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group is substituted Or an amino group which may have a group selected from the group consisting of 6 alkyl group [in which at least one group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group is substituted on a phenyl ring Or a piperidinyl group (on the piperidine ring, at least one amino group may be substituted. On the amino group, a phenyl group [a halogen atom on a phenyl ring, a halogen, At least one of a group selected from the group consisting of a substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted] and a C1-6 alkyl group And at least one of the groups selected from the group may be substituted.
R ⁵⁴ is selected from the group consisting of a phenyl C1-6 alkyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group And at least one of the groups may be substituted).
R ⁵⁵ is selected from the group consisting of a phenyl C1-6 alkyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group Or at least one of the groups may be substituted or a phenyl group (on the phenyl ring, from a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group At least one of the groups selected from the group consisting of
The total carbon number of the group -CHR ⁵² R ⁵⁵ in the general formula (F3-3) does not exceed 6. ]
The reaction of compound (F3-1) with compound (20) is carried out under the same reaction conditions as the reaction of compound (Fd-1) with compound (15) in the aforementioned Reaction scheme-18.

  The reaction of compound (F3-1) with compound (21) is carried out under the same reaction conditions as the reaction of compound (E-2) with compound (13) in the aforementioned Reaction scheme-16.

[Wherein, R ^1a , n, X, m, R ⁴⁷ and R ⁴⁸ are as defined above. ]
The reaction of compound (E18-1) with compound (27) is carried out in a suitable inert solvent, in the presence or absence of a basic compound.

  Examples of the basic compound to be used include inorganic basic compounds such as sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate and potassium carbonate, alkali metal salts of fatty acids such as sodium acetate, piperidine, triethylamine, trimethylamine, Pyridine, dimethylaniline, N-ethyldiisopropylamine, dimethylaminopyridine, N-methylmorpholine, 1,5-diazabicyclo [4.3.0] nonene-5 (DBN), 1,8-diazabicyclo [5.4.0 Examples are organic bases such as undecene-7 (DBU) and 1,4-diazabicyclo [2.2.2] octane (DABCO).

  The inert solvent to be used may be any solvent as long as it does not adversely affect the reaction, and examples thereof include water, aromatic hydrocarbons such as benzene, toluene and xylene, diethyl ether, tetrahydrofuran, dioxane, monoglyme, Ethers such as diglyme, halogenated hydrocarbons such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, lower alcohols such as methanol, ethanol, isopropanol, butanol, tert-butanol and ethylene glycol, fatty acids such as acetic acid, ethyl acetate And esters such as methyl acetate, ketones such as acetone and methyl ethyl ketone, acetonitrile, pyridine, dimethyl sulfoxide, N, N-dimethylformamide, hexamethylphosphoric acid triamide, and mixed solvents thereof. Can.

  The compound (27) is generally used in an amount of at least equimolar amount, preferably about equimolar to 5-fold molar amount, relative to compound (E18-1).

  The reaction temperature is usually room temperature to 200 ° C., preferably about room temperature to 150 ° C., and the reaction is generally completed in about 5 minutes to 30 hours.

[Wherein, R ^1a , n, X, m, X ² and R ⁵² are as defined above.
R ^47a represents a hydrogen atom.
R ^48a is a hydrogen atom, a C1-6 alkyl group, a phenyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group At least one of the groups selected from the group may be substituted) or pyridyl group (on the pyridine ring, at least one halogen-substituted or unsubstituted C1-6 alkyl group may be substituted) ).
R ^{47 b} is selected from the group consisting of a C1-6 alkyl group; a phenyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group And at least one of the above-mentioned groups may be substituted or a pyridyl group (on the pyridine ring, at least one halogen-substituted or unsubstituted C1-6 alkyl group may be substituted).
R ^47c represents a hydrogen atom or a C1-6 alkyl group.
The total carbon number of CHR ^47c R ⁵² constituting the group -CH = N-N (R ^48a ) CHR ^47c R ⁵² in the general formula (Ea18-5) does not exceed 6. ]
The reaction of compound (E18-3) with compound (28) is carried out under the same reaction conditions as the reaction of compound (Fd-1) with compound (15) in the aforementioned Reaction scheme-18.

  The reaction of compound (E18-3) with compound (29) is carried out under the same reaction conditions as the reaction of compound (E-2) with compound (13) in the aforementioned Reaction scheme-16.

[Wherein, R ^1a , n, X, m, W and o are the same as above]. R ^14Ab and R ^14c are independently an C1~6 alkoxy group. ]
The reaction for converting the compound (Eaa17-6) to the compound (Eaa17-7) is carried out under the same reaction conditions as the reaction for converting the compound (E-1) to the compound (E-2) in the aforementioned Reaction scheme-16. .

[Wherein, R ^1a , n, X, m, W, o, R ^14Aa and the dotted line on the piperidine ring are the same as above]. When the dotted line on the piperidine ring indicates a double bond, it is assumed that a hydroxyl group is substituted.
R ⁵⁷ is a phenyl group (on the phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group, a halogen-substituted or unsubstituted C1-6 alkoxy group, a C1-4 alkylenedioxy group, a C1 6 having a group selected from the group consisting of alkoxycarbonyl group, cyano group, C2-6 alkenyl group, nitro group, phenyl group, phenyl group as a substituent, C1-6 alkyl group, carbamoyl group and C1-6 alkanoyl group Amino group, C1-6 alkanoyl substituted C1-6 alkyl group, hydroxyl group, C1-6 alkoxycarbonyl substituted C1-6 alkyl group, phenyl C1-6 alkyl group, C1-6 alkanoyl group, C1-6 alkylthio group, 1 , 2,4-triazolyl group, isoxazolyl group, imidazolyl group, benzothiazolyl group, 2H-benzo Loazolyl group, pyrrolyl group, benzoxazolyl group, piperazinyl group [C.sub.1-6 alkoxycarbonyl group on the piperazine ring and phenyl C.sub.1-6 alkyl group (on the phenyl ring, a halogen atom, halogen substituted or unsubstituted At least one group selected from the group consisting of a group selected from the group consisting of a C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted) [Optionally substituted], piperidinyl group [in the piperidine ring, at least one amino group may be substituted. On the amino group, a C1-6 alkyl group and a phenyl group Are selected from the group consisting of halogen atoms, halogen substituted or unsubstituted C.sub.1-6 alkyl groups and halogen substituted or unsubstituted C.sub.1-6 alkoxy groups. At least one group selected from the group consisting of at least one of the substituted groups may be substituted), and at least one group selected from the group consisting of a carbamoyl group is (Which may be substituted). ]
The reaction of compound (Eaa4-1) with compound (31) is carried out in the presence of a condensing agent in a suitable solvent.

  As the solvent used here, in the reaction of the compound (Ea-2) of the aforementioned reaction scheme 19 with the compound (18), the amine halide (Ea-2) is reacted with the carboxylic acid halide of the method (d) Any of the solvents used in the preparation can be used.

  As the condensing agent, for example, a mixture of azo carboxylates and a phosphorus compound can be mentioned. Examples of azocarboxylates include diethyl azodicarboxylate and tert-butyl azodicarboxylate, and examples of phosphorus compounds include triphenylphosphine and the like. The triphenylphosphine may be supported by a suitable polymer. Such triphenyl phosphines are commercially available, for example, under trade names such as triphenyl phosphine polymer suported.

  The condensing agent is generally used in an amount of at least equimolar amount, preferably about equimolar to 3-fold molar amount, relative to the compound (Eaa4-1).

  The compound (31) is generally used in an amount of at least equimolar amount, preferably about equimolar to 2-fold molar amount, relative to compound (Eaa4-1).

  The reaction suitably proceeds usually at 0 to 200 ° C., preferably at about 0 to 150 ° C., and is generally completed in about 1 to 10 hours.

[Wherein, R ^1a , n, X, m, X ² and R ⁵² are as defined above.
R ^46a represents a C1-6 alkoxycarbonyl group.
R ^{46 b} is a phenyl group (on the phenyl ring, at least one of a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group Species may be substituted, phenyl C.sub.1-6 alkyl groups (on the phenyl ring, from halogen atoms, halogen substituted or unsubstituted C.sub.1-6 alkyl groups and halogen substituted or unsubstituted C.sub.1-6 alkoxy groups. At least one member selected from the group consisting of: a phenyl C.sub.1-6 alkoxycarbonyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen) At least one of a group selected from the group consisting of a substituted or unsubstituted C1-6 alkoxy group may be substituted) or a C1-6 alkoxy Indicates a carbonyl group.
R ^{46 c} is a phenyl group (on the phenyl ring, at least one of a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group Or a phenyl C1-6 alkyl group (on the phenyl ring, from a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group And at least one of the groups selected from the group consisting of )
R ^{46 d} is a phenyl group (on the phenyl ring, at least one of a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group The species may be substituted) or a C1-6 alkyl group. ]
The reaction for converting the compound (E14-1) to the compound (E14-2) is carried out under the same reaction conditions as the reaction for converting the compound (E-1) to the compound (E-2) in the aforementioned Reaction scheme-16. .

  The reaction of compound (E14-2) with compound (32) is carried out in the presence of a condensing agent in a suitable solvent.

  As the solvent, the solvent used when reacting the amine halide (Ea-2) with the carboxylic acid halide of the method (ii) in the reaction of the compound (Ea-2) of the aforementioned reaction scheme 19 with the compound (18) Either can be used.

  As a condensing agent, N, N'- carbonyl diimidazole etc. can be mentioned, for example.

  The compound (32) and the condensing agent may be used in an amount of at least 1 mol, preferably about 1 to 2 mol, per 1 mol of the compound (E14-2). The reaction is usually carried out at 0 to 150 ° C., preferably at about 0 to 100 ° C., and generally completed in about 1 to 30 hours.

  The reaction of compound (E14-2) with compound (33) is carried out under the same reaction conditions as the reaction of compound (E-2) with compound (13) in the aforementioned Reaction scheme-16.

  The reaction of compound (E14-2) with compound (34) is carried out under the same reaction conditions as the reaction of compound (Fd-1) with compound (15) in the aforementioned Reaction scheme-18.

[Wherein, R ^1a , n and o are as defined above.
R ^24a and R ^25a form a piperazine ring via the nitrogen atom to which they are adjacent. On the piperazine ring, a C1 to 6 alkoxycarbonyl group; a benzoyl group (on a phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1 to 6 alkyl group and a halogen substituted or unsubstituted C1 to 6 alkoxy group At least one of the groups selected from the group may be substituted; phenoxy group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1 6 at least one group selected from the group consisting of alkoxy groups may be substituted; phenyl C1-6 alkyl group (on the phenyl ring, a halogen atom, halogen substituted or unsubstituted C1-6 alkyl group And at least one group selected from the group consisting of halogen-substituted or unsubstituted C1-6 alkoxy groups Phenyl C1-6 alkoxycarbonyl group (on the phenyl ring, a group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group At least one selected group may be substituted; phenyl C2-6 alkenyl group (wherein a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted on the phenyl ring) And at least one of a group selected from the group consisting of a C1-6 alkoxy group may be substituted) and a phenyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen) At least one of a group selected from the group consisting of a substituted or unsubstituted C.sub.1-6 alkoxy group is substituted; At least one of selected from the group consisting also be) groups may be substituted. However, it is assumed that a C1-6 alkoxycarbonyl group is substituted on the nitrogen atom of the piperazine ring.
R ⁵⁸ is a phenyl group (on the phenyl ring, a group selected from the group consisting of a halogen atom as a substituent, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group And at least one of them may be substituted).
R ^24b and R ^25b form a piperazine ring via the adjacent nitrogen atom. On the piperazine ring, a C1 to 6 alkoxycarbonyl group; a benzoyl group (on a phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1 to 6 alkyl group and a halogen substituted or unsubstituted C1 to 6 alkoxy group At least one of the groups selected from the group may be substituted; phenoxy group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1 6 at least one group selected from the group consisting of alkoxy groups may be substituted; phenyl C1-6 alkyl group (on the phenyl ring, a halogen atom, halogen substituted or unsubstituted C1-6 alkyl group And at least one group selected from the group consisting of halogen-substituted or unsubstituted C1-6 alkoxy groups Phenyl C1-6 alkoxycarbonyl group (on the phenyl ring, a group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group At least one selected group may be substituted; phenyl C2-6 alkenyl group (wherein a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted on the phenyl ring) And at least one of a group selected from the group consisting of a C1-6 alkoxy group may be substituted) and a phenyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen) At least one of a group selected from the group consisting of a substituted or unsubstituted C.sub.1-6 alkoxy group is substituted; At least one of selected from the group consisting also be) groups may be substituted. However, a hydrogen atom is bonded to the nitrogen atom of the piperazine ring.
R ^24c and R ^25c form a piperazine ring via the adjacent nitrogen atom. On the piperazine ring, a C1 to 6 alkoxycarbonyl group; a benzoyl group (on a phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1 to 6 alkyl group and a halogen substituted or unsubstituted C1 to 6 alkoxy group At least one of the groups selected from the group may be substituted; phenoxy group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1 6 at least one group selected from the group consisting of alkoxy groups may be substituted; phenyl C1-6 alkyl group (on the phenyl ring, a halogen atom, halogen substituted or unsubstituted C1-6 alkyl group And at least one group selected from the group consisting of halogen-substituted or unsubstituted C1-6 alkoxy groups Phenyl C1-6 alkoxycarbonyl group (on the phenyl ring, a group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group At least one selected group may be substituted; phenyl C2-6 alkenyl group (wherein a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted on the phenyl ring) And at least one of a group selected from the group consisting of a C1-6 alkoxy group may be substituted) and a phenyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen) At least one of a group selected from the group consisting of a substituted or unsubstituted C.sub.1-6 alkoxy group is substituted; At least one of selected from the group consisting also be) groups may be substituted. However, on the nitrogen atom of the piperazine ring, a phenyl C.sub.1-6 alkoxycarbonyl group (a halogen atom as a substituent, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1 group on the phenyl ring are exemplified. -6 alkoxy group may be substituted at least one group selected from the group consisting of). ]
The reaction for converting the compound (Fca12-1) to the compound (Fca12-2) is carried out under the same reaction conditions as the reaction for converting the compound (E-1) to the compound (E-2) in the aforementioned Reaction scheme-16. .

  The reaction of compound (Fca12-2) with compound (36) is carried out under the same reaction conditions as the reaction of compound (E14-2) with compound (32) in the aforementioned Reaction scheme-25.

[Wherein, R ^1a and n are as defined above. R ^45a represents a C1-6 alkoxycarbonyl group. R ^{46a ′} is a phenyl group (on the phenyl ring, at least one of a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group 1 is optionally substituted). ]
The reaction for converting the compound (Fd-39-1) to the compound (Fd-39-2) is the same reaction condition as the reaction for converting the compound (E-1) to the compound (E-2) in the aforementioned Reaction scheme-16. It takes place below.

  The reaction of compound (Fd-39-2) with compound (37) is carried out under the same reaction conditions as the reaction of compound (E14-2) with compound (32) in the aforementioned Reaction scheme 25.

[Wherein, R ^1a , X, n, m, W and o are the same as above]. R ^{7a ′} represents a hydrogen atom, a hydroxyl group, a C1-6 alkoxy group or a phenyl group (a halogen atom may be substituted on the phenyl ring). The dotted line on the piperidine ring indicates that it may be a double bond. When the dotted line is a double bond, a hydroxyl group is substituted on the piperidine ring. R ^{6a ′} represents a tetrahydropyranyloxy group. R ^{17 ′} is a C1-6 alkyl group or a phenyl group (on the phenyl ring, a group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group And at least one of the selected groups may be substituted). M represents an alkali metal such as sodium or potassium. ]
The reaction to give compound (14 ′) to compound (15 ′) is carried out in the presence of an acid in a suitable solvent or in the absence of a solvent.

  As the solvent, any solvent which does not affect the reaction can be used. For example, water, halogenated hydrocarbons such as dichloromethane, chloroform and carbon tetrachloride, lower alcohols such as methanol, ethanol and isopropanol, acetone, methyl ethyl ketone and the like Ketones, dioxane, tetrahydrofuran, ethers such as ethylene glycol monomethyl ether and ethylene glycol dimethyl ether, fatty acids such as formic acid and acetic acid, mixed solvents of these, and the like.

  Examples of the acid include mineral acids such as hydrochloric acid, sulfuric acid and hydrobromic acid, and organic acids such as formic acid, trifluoroacetic acid, acetic acid, pyridinium p-toluenesulfonic acid, aromatic sulfonic acid such as p-toluenesulfonic acid and the like. be able to. The amount of the acid used is not particularly limited and can be appropriately selected from a wide range, but it is usually about 0.1 to 10 mol, preferably about 0.1 to 2 mol, per 1 mol of the compound (14 '). Good.

  The reaction suitably proceeds usually at about 0 to 200 ° C., preferably at about room temperature to 150 ° C., and is usually completed in about 0.5 to 50 hours.

  The reaction of compound (15 ') with compound (16') or (17 ') is carried out in the presence or absence of a basic compound, preferably in the absence of a suitable inert solvent or no solvent.

  Examples of the basic compound to be used herein include triethylamine, trimethylamine, pyridine, dimethylaniline, N-ethyldiisopropylamine, dimethylaminopyridine, N-methylmorpholine, 1,5-diazabicyclo [4.3.0] nonene-5. Organic bases such as (DBN), 1,8-diazabicyclo [5.4.0] undecene-7 (DBU), 1,4-diazabicyclo "[2.2.2] octane (DABCO), sodium carbonate, potassium carbonate , Carbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate, metal hydroxides such as sodium hydroxide, potassium hydroxide and calcium hydroxide, potassium hydride, sodium hydride, sodium hydride, potassium, sodium, sodium amide, sodium methylate, Metal alcoholates such as sodium ethylate Inorganic bases.

  As the solvent to be used, for example, halogenated hydrocarbons such as chloroform, dichloromethane, dichloroethane and carbon tetrachloride, aromatic hydrocarbons such as benzene, toluene and xylene, diethyl ether, diisopropyl ether, tetrahydrofuran, dimethoxyethane and the like Ethers, esters such as methyl acetate, ethyl acetate and isopropyl acetate, methanol, ethanol, isopropanol, propanol, butanol, 3-methoxy-1-butanol, alcohols such as ethyl cellosolve and methyl cellosolve, acetonitrile, pyridine, acetone, Aprotic polar solvents such as water, N, N-dimethylacetamide, N, N-dimethylformamide, dimethylsulfoxide, hexamethylphosphoric acid triamide etc. or mixed solvents thereof .

  The amount of compound (16 ′) or (17 ′) used is usually about equimolar to 5 times the molar amount, preferably about equimolar to 3 times the molar amount, relative to the compound (15 ′) Good.

  The reaction is carried out usually at a temperature of about 0 to 200 ° C., preferably at about room temperature to about 150 ° C., usually for about 5 minutes to 30 hours.

  A boron compound such as boron trifluoride diethyl ether complex or a copper halide compound such as cuprous chloride may be added to the reaction system of the reaction.

  In the reaction of the compound (15 ') with the compound (17'), the reaction proceeds advantageously when an organic acid such as trifluoroacetic acid is added to the reaction system.

[Wherein, R ^1a , X, n, m, W, R ^{7a ′} , X ² and o are the same as above]. Two W in the general formulas (1c ′) to (1g ′) may be the same or different.

R ^{9a ′} represents a hydrogen atom.

R ^{10a ′} is a hydrogen atom; a C1-6 alkyl group which may have a hydroxyl group as a substituent; a C1-6 alkanoyl group; a C1-6 alkoxycarbonyl group; a phenyl C1-6 alkoxycarbonyl group (on the phenyl ring And at least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group as a substituent may be substituted); Phenyl group (on the phenyl ring, a halogen atom as a substituent, a halogen substituted or unsubstituted C1-6 alkyl group, a halogen substituted or unsubstituted C1-6 alkoxy group, a C1-6 alkanoyl group as a substituent and a C1 Amino group which may have a group selected from the group consisting of 6 alkyl groups, C1-6 alkoxycarbonyl group, phenyl group A phenoxy group (on the phenyl ring, at least one of a group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group, and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group is substituted Aminosulfonyl group, 1,2,3,4-tetrahydroquinolyl group (1,2,3,4-tetrahydroquinoline ring on which at least one oxo group is substituted as a substituent) C1-6 alkylsulfonyl group, C3-8 cycloalkyl group, nitro group, cyano group, C1-6 alkylthio group; phenylsulfonyl group (on the phenyl ring, a halogen atom as a substituent, halogen substitution or At least one of the groups selected from the group consisting of unsubstituted C1-6 alkyl and halogen substituted or unsubstituted C1-6 alkoxy is substituted May be substituted), hydroxyl-substituted C.sub.1-6 alkyl groups and groups

(W ₁ represents a C 1-6 alkylene group, and R ^{11 ′} and R ^{12 ′} are the same or different and represent a C 1-6 alkoxy group.) At least one of the groups selected from the group consisting of Phenyl C1-6 alkyl group (in the phenyl ring, a C1 to 4 alkylenedioxy group as a substituent, a phenyl group (on the phenyl ring, a halogen atom, halogen substituted or unsubstituted C1 6 alkyl group and at least one member selected from the group consisting of halogen substituted or unsubstituted C1-6 alkoxy group may be substituted), a group -N ( ^{R11A '} ) ^R12A' ( ^{R11A '} and ^{R12A '} is the same or different and represents a hydrogen atom, a C1-6 alkyl group or a phenyl group, and R11A ^' and ^{R12A '} together with adjacent nitrogen atoms via or through a nitrogen atom, an oxygen atom or a sulfur atom Without each other 5 to 7 membered saturated heterocyclic ring), a phenoxy group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 At least one selected from the group consisting of alkoxy groups may be substituted), phenyl C1-6 alkoxy group, amino group substituted C1-6 alkoxy group which may have C1-6 alkyl group as a substituent, At least one group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-10 alkoxy group may be substituted); benzofuryl C1 6 alkyl group [in the benzofuran ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1 C.sub.1 group. At least one of a group selected from the group consisting of an alkoxy group may be substituted; a phenylsulfonyl group (on a phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group, a halogen substituted Or at least one of a group selected from the group consisting of an unsubstituted C1-6 alkoxy group and a C1-4 alkylenedioxy group may be substituted); a phenoxycarbonyl group (on the phenyl ring, a substituent group And at least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted; To a 6 alkenyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted At least one group selected from the group consisting of C1-6 alkoxy groups may be substituted); C1-6 alkoxy substituted C1-6 alkyl group; C2-6 alkenyl group; C1-6 alkoxy substituted C2 To 6 alkanoyl groups; C3-8 cycloalkyl substituted C1-6 alkyl groups; phenoxy C1-6 alkyl groups (on the phenyl ring, halogen atoms, halogen substituted or unsubstituted C1-6 alkyl groups and halogen substituted or unsubstituted And at least one group selected from the group consisting of C1-6 alkoxy groups may be substituted; benzoyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group) And at least one of a group selected from the group consisting of halogen substituted or unsubstituted C1-6 alkoxy group may be substituted); phenyl (In the phenyl ring, at least one of a group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group is substituted. Pyridyl group; pyridyl C1-6 alkyl group; imidazolyl C1-6 alkyl group; 1,2,3,4-tetrahydroquinolyl group (on a 1,2,3,4-tetrahydroquinoline ring And at least one of a group selected from the group consisting of an oxo group and a C1-6 alkyl group as a substituent may be substituted); quinolyl group; indolyl group; having a C1-6 alkyl group as a substituent Indazolyl group; naphthyl group; C3-8 cycloalkyl group; amino substituted C1 which may have C1-6 alkyl group as a substituent 6 alkyl group; cyano C1~6 alkyl group; furyl substituted C1~6 alkyl group, group

[RR is a phenyl group (on the phenyl ring, at least one of the groups selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group. The species is optionally substituted). Or a piperazinyl substituted C1-6 alkyl group (on the piperazine ring, at least one phenyl group as a substituent [on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or At least one member selected from the group consisting of unsubstituted C.sub.1-6 alkoxy groups may be substituted).

R ^{9b ′} is a hydrogen atom; a C1-6 alkyl group which may have a hydroxyl group as a substituent; a phenyl group (on a phenyl ring, a C1 to 4 alkylenedioxy group as a substituent, a phenyl group (on a phenyl ring At least one member selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group may be substituted), a group -N (R ^{11A ′} ) R ^{12A ′} (R ^{11A ′} and R ^{12A ′} are the same or different and each represents a hydrogen atom, a C1-6 alkyl group or a phenyl group. R ^{11A ′} and R ^{12A ′} together with the adjacent nitrogen atom , A 5- to 7-membered saturated heterocyclic ring may be bonded to each other via or without a nitrogen atom, an oxygen atom or a sulfur atom, a phenoxy group (on the phenyl ring, a halogen atom, a halogen substitution or At least one member selected from the group consisting of a substituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group may be substituted), a phenyl C1-6 alkoxy group, a C1-as a substituent Selected from the group consisting of an amino group-substituted C1-6 alkoxy group which may have 6 alkyl groups, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-10 alkoxy group At least one kind of the group may be substituted); phenyl C1-6 alkyl group (in the phenyl ring, a C1-4 alkylenedioxy group as a substituent, a phenyl group (a halogen atom in the phenyl ring, At least one selected from the group consisting of halogen-substituted or unsubstituted C1-6 alkyl groups and halogen-substituted or unsubstituted C1-6 alkoxy groups May also be one species substituted), group ^{-N (R 11A ') R 12A} ' (R 11A ' and R ^12A' are the same or different and each is hydrogen atom, Cl to 6 alkyl or phenyl And R ^{11A ′} and R ^{12A ′} may be bonded to each other to form a 5- to 7-membered saturated heterocycle, together with adjacent nitrogen atoms, with or without a nitrogen atom, an oxygen atom or a sulfur atom) A phenoxy group (in which at least one member selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group is substituted on the phenyl ring , A phenyl C1-6 alkoxy group, an amino group substituted C1-6 alkoxy group which may have a C1-6 alkyl group as a substituent, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halo At least one group selected from the group consisting of substituted or unsubstituted C.sub.1-10 alkoxy groups may be substituted); benzofuryl [a halogen atom, a halogen substituted or unsubstituted C.sub.1 or the like on the benzofuran ring; At least one of a group selected from the group consisting of a -6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group may be substituted]; a benzofuryl C1-6 alkyl group [on the benzofuran ring, At least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted]; C1 to C6 Alkoxy substituted C1-6 alkyl group; C3-8 cycloalkyl substituted C1-6 alkyl group; C3-8 cycloalkyl group; phenoxy C1-6 ar Group (on the phenyl ring, at least one of a group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group is substituted Pyridyl group; pyridyl C1-6 alkyl group; imidazolyl group; imidazolyl C1-6 alkyl group; amino substituted C1-6 alkyl group which may have a C1-6 alkyl group as a substituent; cyano substituted C1 To 6 alkyl groups; furyl substituted C1-6 alkyl groups; furyl groups; piperazinyl groups (on the piperazine ring, at least one phenyl group as a substituent [on the phenyl ring, a halogen atom, halogen substituted or unsubstituted At least one of the groups selected from the group consisting of a C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group (A species may be substituted) or a piperazinyl substituted C.sub.1-6 alkyl group (on the piperazine ring, at least one phenyl group as a substituent [a halogen atom on the phenyl ring And at least one of a group selected from the group consisting of a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted Good).

R ^{9c ′} is a C1-6 alkyl group which may have a hydroxyl group as a substituent; C1-6 alkoxycarbonyl group; phenyl C1-6 alkoxycarbonyl group (on the phenyl ring, a halogen atom as a substituent, halogen substitution or At least one of a group selected from the group consisting of an unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted; a phenyl group (on the phenyl ring) Or a substituent selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group, a halogen substituted or unsubstituted C1-6 alkoxy group, and a substituent C1-6 alkanoyl group and a C1-6 alkyl group Amino group which may have a substituted group, C1-6 alkoxycarbonyl group, phenyl group, phenoxy group (on the phenyl ring, At least one selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group), an aminosulfonyl group 1,2,3,4-tetrahydroquinolyl group (wherein at least one oxo group may be substituted as a substituent on the 1,2,3,4-tetrahydroquinoline ring), C1-6 alkyl A sulfonyl group, a C3-8 cycloalkyl group, a nitro group, a cyano group, a C1-6 alkylthio group; a phenylsulfonyl group (on the phenyl ring, a halogen atom as a substituent, a halogen substituted or unsubstituted C1-6 alkyl group and At least one member selected from the group consisting of halogen-substituted or unsubstituted C1-6 alkoxy groups may be substituted), hydroxyl-substituted C1 6 alkyl group and group

(W ₁ represents a C 1-6 alkylene group, and R ^{11 ′} and R ^{12 ′} are the same or different and represent a C 1-6 alkoxy group.) At least one of the groups selected from the group consisting of A phenyl C1-6 alkyl group (in the phenyl ring, a C1 to 4 alkylenedioxy group as a substituent, a phenyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1 to C6 alkyl group; At least one member selected from the group consisting of an alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted), a group -N ( ^{R11A '} ) ^R12A' ( ^{R11A '} and R) ^{12A '} is the same or different and represents a hydrogen atom, a C1-6 alkyl group or a phenyl group, and R11A ^' and ^{R12A '} together with adjacent nitrogen atoms via or through a nitrogen atom, an oxygen atom or a sulfur atom Not tied to each other 77-membered saturated heterocyclic ring may be formed), phenoxy group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group At least one member selected from the group consisting of: a phenyl C1-6 alkoxy group, an amino group substituted C1-6 alkoxy group which may have a C1-6 alkyl group as a substituent, a halogen atom And at least one selected from the group consisting of a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-10 alkoxy group may be substituted; benzofuryl C1-6 alkyl Group [on the benzofuran ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkyl group. At least one group selected from the group consisting of Coxy groups may be substituted]; phenylsulfonyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group, a halogen substituted Or at least one of a group selected from the group consisting of an unsubstituted C1-6 alkoxy group and a C1-4 alkylenedioxy group may be substituted; phenyl C2-6 alkenyl group (on the phenyl ring) And at least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted); 6 alkoxy substituted C1-6 alkyl group; C2-6 alkenyl group; C3-8 cycloalkyl group substituted C1-6 alkyl group; phenoxy C1-6 alkyl group (On the phenyl ring, at least one of a group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group is substituted Pyridyl group; pyridyl C1-6 alkyl group; imidazolyl C1-6 alkyl group; 1,2,3,4-tetrahydroquinolyl group (substituted on the 1,2,3,4-tetrahydroquinoline ring) At least one group selected from the group consisting of oxo group and C1-6 alkyl group may be substituted as a group); quinolyl group; indolyl group; indazolyl group; naphthyl group; C3-8 cycloalkyl group; Amino-substituted C1-6 alkyl group which may have C1-6 alkyl group as a substituent; cyano-substituted C1-6 alkyl group; furyl-substituted C1-6 alkyl , Based on

[RR is a phenyl group (on the phenyl ring, at least one of the groups selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group. The species is optionally substituted). Or a piperazinyl substituted C1-6 alkyl group (on the piperazine ring, at least one phenyl group as a substituent [on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or At least one member selected from the group consisting of unsubstituted C.sub.1-6 alkoxy groups may be substituted).

R ^{9 d ′} is a C1 to 6 alkanoyl group; a group comprising a phenoxycarbonyl group (on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C1 to 6 alkyl group and a halogen substituted or unsubstituted C1 to 6 alkoxy group Or C.sub.1-6 alkoxy-substituted C.sub.2-6 alkanoyl group or benzoyl group (on the phenyl ring, a halogen atom, halogen-substituted or unsubstituted C.sub.1-6). And at least one group selected from the group consisting of an alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted).

R ^{9e ′} is a phenyl group (on the phenyl ring, at least a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group 1 is optionally substituted).

R ^{18 ′} represents a hydrogen atom or a C1 to 6 alkyl group.

The dotted line on the piperidine ring indicates that it may be a double bond. When the dotted line is a double bond, group ^{- (W) oNR 9a 'R} 10a', group ^{- (W) oN (CHR 18} 'R 9b') R 10a ', group ^{- (W) oNR 9c' R} 10a ' And the group-(W) oNR ^{9d '} R ^10a' or the group-(W) oN (CONHR ^{9a '} ) R ^10a' is substituted.

The total number of carbon atoms in the 'group -N in (R ^10a formula ^{(1d)') CHR 18 CHR} 18 constituting the 'R ^9b' 'R ^9b' shall not exceed 6. ]
The reaction of compound (1c ′) with compound (16 ′) is carried out without solvent or in a suitable solvent in the presence of a reducing agent.

  The amount of the compound (16 ') to be used is generally at least an equimolar amount, preferably an equimolar to a large excess amount, relative to the compound (1c').

  Examples of the solvent used in the reaction include lower alcohols such as water, methanol, ethanol, isopropanol, butanol, tert-butanol and ethylene glycol, fatty acids such as acetonitrile, formic acid, acetic acid and trifluoroacetic acid, diethyl ether, Ethers such as tetrahydrofuran, dioxane, monoglyme and diglyme, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and mixed solvents thereof .

  As the reducing agent, for example, an alkali metal salt of formate such as formic acid and sodium formate, sodium borohydride, sodium cyanoborohydride, sodium triacetyloxyborohydride, a hydride reducing agent such as lithium aluminum hydride or the like A mixture of hydrogenation reducing agents, catalytic hydrogen reducing agents such as palladium-black, palladium-carbon, platinum oxide, platinum black, Raney nickel and the like can be exemplified.

  When formic acid and an alkali metal formate salt are used as the reducing agent, the reaction temperature is usually about room temperature to 200 ° C., preferably about 50 to 150 ° C., and the reaction is completed in about 10 minutes to 10 hours. The amount of formic acid used is preferably in a large excess relative to the compound (1c ').

  When a hydrogenation reducing agent is used, the reaction temperature is usually about −80 to 100 ° C., preferably about −80 to 70 ° C., and the reaction is completed in about 30 minutes to 100 hours. The amount of the hydrogenation reducing agent to be used is generally equimolar to 20 times molar amount, preferably equimolar to 6 times molar, with respect to compound (1c '). In particular, when lithium aluminum hydride is used as the hydrogenation reducing agent, it is preferable to use, as a solvent, ethers such as diethyl ether, tetrahydrofuran, dioxane, monoglyme and diglyme, and aromatic hydrocarbons such as benzene, toluene and xylene. . Even in the reaction system of the reaction, amines such as trimethylamine, triethylamine and N-ethyldiisopropylamine, and molecular sieves such as molecular sieves 3A (MS-3A) and molecular sieves 4A (MS-4A) can be added. Good.

  Furthermore, when a catalytic hydrogen reducing agent is used, it is usually in a hydrogen atmosphere of about normal pressure to 20 atm, preferably about normal pressure to 10 atm, or a hydrogen donor such as formic acid, ammonium formate, cyclohexene, water release hydrazine, etc. The reaction is preferably carried out at a temperature of about -30 to 100 ° C, preferably about 0 to 60 ° C, in the presence, and the reaction is usually completed in about 1 to 12 hours. The amount of the catalytic hydrogen reducing agent to be used is generally about 0.1 to 40% by weight, preferably about 1 to 20% by weight, relative to the compound (1c ′).

  The reaction of compound (1c ') with compound (17') is generally carried out in a suitable solvent, in the presence or absence of a basic compound.

  As an inert solvent to be used, for example, aromatic hydrocarbons such as benzene, toluene and xylene, ethers such as diethyl ether, tetrahydrofuran, dioxane, monoglyme and diglyme, halogens such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride Lower hydrocarbons such as methanol, ethanol, isopropanol, butanol, tert-butanol and ethylene glycol, fatty acids such as acetic acid, esters such as ethyl acetate and methyl acetate, ketones such as acetone and methyl ethyl ketone, acetonitrile, Pyridine, dimethylsulfoxide, N, N-dimethylformamide, hexamethylphosphoric acid triamide or a mixed solvent thereof can be mentioned.

  Examples of the basic compound include carbonates such as sodium carbonate, potassium carbonate, sodium hydrogencarbonate, potassium hydrogencarbonate and cesium carbonate, metal hydroxides such as sodium hydroxide, potassium hydroxide and calcium hydroxide, sodium hydride , Metal hydrides such as potassium hydride, potassium, sodium, sodium amide, sodium methylate, sodium ethylate, sodium n-butoxide, pyridine, imidazole, N-ethyldiisopropylamine, dimethylaminopyridine, triethylamine, trimethylamine, dimethylaniline , N-methylmorpholine, 1,5-diazabicyclo [4.3,0] nonene-5 (DBN), 1,8-diazabicyclo [5.4.0] undecene-7 (DBU), 1,4-diazabicyclo [5] 2.2. ] Can be exemplified organic bases or mixtures thereof, such as octane (DABCO).

  The basic compound is used in an amount of at least equimolar amount, preferably equimolar to 10-fold molar amount relative to compound (1c ′).

  The compound (17 ') is used in an amount of at least equimolar, preferably equimolar to 10-fold molar, relative to the compound (1c').

  The reaction is usually carried out at 0 to 200 ° C., preferably about 0 to 150 ° C., and the reaction is completed generally in about 5 minutes to 80 hours.

  An alkali metal halogen compound such as sodium iodide or potassium iodide may be added to the reaction system, or a phase transfer catalyst may be added.

  Here, as a phase transfer catalyst, for example, tetrabutyl ammonium chloride, tetrabutyl ammonium bromide, tetrabutyl ammonium fluoride, tetrabutyl ammonium iodide, tetrabutyl ammonium hydroxide, tetrabutyl ammonium hydrogen sulfite, tributyl methyl ammonium chloride, tributyl Benzyl ammonium chloride, tetrapentyl ammonium chloride, tetrapentyl ammonium bromide, tetrahexyl ammonium chloride, benzyl dimethyl octyl ammonium chloride, methyl trihexyl ammonium chloride, benzyl dimethyl octadecanyl ammonium chloride, methyl tridecanyl ammonium chloride, benzyl tripropyl ammonium Chloride, Benzi It is selected from the group consisting of a linear or branched alkyl group having 1 to 18 carbon atoms such as triethyl ammonium chloride, phenyl triethyl ammonium chloride, tetraethyl ammonium chloride, tetramethyl ammonium chloride, phenyl C1-6 alkyl group and phenyl group Quaternary ammonium salt substituted with a substituted group, phosphonium salt substituted with a linear or branched alkyl group having 1 to 18 carbon atoms such as tetrabutylphosphonium chloride, 1 carbon atom such as 1-dodecanyl pyridinium chloride Examples thereof include pyridinium salts and the like in which a linear or branched alkyl group of up to 18 is substituted.

  The amount of phase transfer catalyst used is usually 0.1 to 1 mole, and preferably 0.1 to 0.5 mole, per mol of compound (1c ′).

  The reaction of the compound (1c ') with the compound (18') is a method of reacting the compound (1c ') with the carboxylic acid of the compound (18') in a usual amide bond forming reaction.

  A wide range of conditions for known amide bond formation reactions can be applied to the amide bond formation reaction. For example, (a) mixed acid anhydride method, that is, a method in which a carboxylic acid (18 ') is reacted with an alkyl halocarboxylic acid to make a mixed acid anhydride and this is reacted with an amine (1c'), (b) active ester method That is, a carboxylic acid (18 ′) is used as an active ester such as p-nitrophenyl ester, N-hydroxysuccinimide ester, 1-hydroxybenzotriazole ester, or an active amide with benzoxazoline-2-thione, Method of reacting amine (1c '), (iii) Carbodiimide method, ie, amine (1c') to dicyclohexylcarbodiimide, 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide (WSC) to carboxylic acid (18 ') A condensation reaction in the presence of an activating agent such as carbonyldiimidazole, (d) other Method, for example, a method of converting carboxylic acid (18 ') into carboxylic acid anhydride with a dehydrating agent such as acetic anhydride, and reacting this with amine (1c'), ester of carboxylic acid (18 ') with lower alcohol and amine ( Examples include a method of reacting 1c ′) under high pressure and temperature, a method of reacting an amine (1c ′) with an acid halide of a carboxylic acid (18 ′), that is, a carboxylic acid halide.

  The mixed acid anhydride used in the above mixed anhydride method (a) is obtained by the usual Schotten-Baumann reaction, and is reacted with an amine (1c ') without usually isolating the compound of the general formula (1f') The compound of the present invention is produced.

  The Schotten-Baumann reaction is carried out in the presence of a basic compound.

  As the basic compound to be used, compounds conventionally used in Schotten-Baumann reaction, such as triethylamine, trimethylamine, pyridine, dimethylaniline, N-ethyldiisopropylamine, dimethylaminopyridine, N-methylmorpholine, 1,5-diazabicyclo [4] .3.0] Nonene-5 (DBN), 1,8-diazabicyclo [5.4.0] undecene-7 (DBU), 1,4-diazabicyclo "[2.2.2] octane (DABCO), etc. Organic bases, carbonates such as sodium carbonate, potassium carbonate, sodium hydrogen carbonate and potassium hydrogen carbonate, metal hydroxides such as sodium hydroxide, potassium hydroxide and calcium hydroxide, potassium hydride, sodium hydride, sodium hydride, potassium sodium , Sodium amide, sodium methylate, natrium Inorganic base metal alcoholates such as ethylate and the like.

  The reaction is usually carried out at about -20 to 100 ° C, preferably about 0 to 50 ° C, and the reaction time is about 5 minutes to 10 hours, preferably about 5 minutes to 2 hours.

  The reaction of the obtained mixed acid anhydride with the amine (1c ') is carried out usually at about -20 to 150 ° C, preferably at about 10 to 50 ° C, and the reaction time is preferably about 5 minutes to 10 hours, preferably It is about 5 minutes to 5 hours. The mixed acid anhydride method is generally carried out in a solvent.

  As the solvent to be used, any of the solvents commonly used in the mixed acid anhydride method can be used. Specifically, halogenated hydrocarbons such as chloroform, dichloromethane, dichloroethane, carbon tetrachloride, benzene, toluene, xylene Aromatic hydrocarbons such as diethyl ether, diisopropyl ether, tetrahydrofuran, ethers such as dimethoxyethane, esters such as methyl acetate, ethyl acetate, isopropyl acetate, N, N-dimethyl acetamide, N, N-dimethyl acetamide Aprotic polar solvents such as formamide, dimethylsulfoxide, hexamethylphosphoric acid triamide and the like, or mixed solvents thereof and the like can be mentioned.

  Examples of the alkyl halocarboxylic acid used in the mixed acid anhydride method include methyl chloroformate, methyl bromoformate, ethyl chloroformate, ethyl bromoformate, isobutyl chloroformate and the like. The ratio of carboxylic acid (18 '), alkyl halocarboxylic acid and amine (1c') to be used in this method is usually equimolar, but it is preferable to use alkylhalocarboxylic acid and carboxylic acid with respect to amine (1c '). Each (18 ') can be used in the range of equimolar to 1.5 times molar amount or so.

  In the method (3) of condensation reaction in the presence of the above-mentioned activating agent, the reaction is carried out in a suitable solvent, in the presence or absence of a basic compound.

  As the solvent and the basic compound used herein, any of the solvents used in the method of reacting an amine (1c ') with a carboxylic acid halide in the following other method (d) can be used.

  The amount of the activating agent used is at least equimolar, preferably equimolar to 5-fold molar, relative to the compound (1c ′). When WSC is used as the activating agent, the reaction proceeds advantageously when 1-hydroxybenzotriazole is added to the reaction system.

  The reaction is usually carried out at about -20 to about 180 ° C, preferably at about 0 to 150 ° C, and the reaction is generally completed in about 5 minutes to about 90 hours.

  Moreover, among the other methods (ii), when a method of reacting an amine (1c ') with a carboxylic acid halide is adopted, the reaction is carried out in a suitable solvent in the presence of a basic compound.

  A wide variety of known basic compounds can be used as the basic compound to be used, and, for example, any of the basic compounds used for the Schotten-Baumann reaction can be used.

  As the solvent to be used, for example, in addition to the solvent used in the above mixed acid anhydride method, alcohols such as methanol, ethanol, isopropanol, propanol, butanol, 3-methoxy-1-butanol, ethyl cellosolve, methyl cellosolve, Acetonitrile, pyridine, acetone, water and the like can be mentioned.

  The use ratio of the amine (1c ′) to the carboxylic acid halide is not particularly limited and may be appropriately selected within a wide range, but generally the latter is at least about equimolar to the former, preferably about 1 to 5 It is preferable to use about double molar amount.

  The reaction is usually carried out at about -20 to 180 ° C, preferably at about 0 to 150 ° C, and the reaction is generally completed in about 5 minutes to 50 hours.

  Furthermore, the above-mentioned amide bond formation reaction includes carboxylic acid (18 ') and amine (1c'), diphenyl phosphinic chloride, phenyl-N-phenyl phosphoramide chloridate, diethyl chlorophosphate, diethyl cyanophosphate, diphenyl phosphate It can also be carried out by a method of reacting in the presence of a condensing agent of a phosphorus compound such as azide or bis (2-oxo-3-oxazolidinyl) phosphinic chloride.

  The reaction is generally carried out in the presence of a solvent and a basic compound used in the method of reacting an amine (1c ') with the above-mentioned carboxylic acid halide, usually at around -20 to 150 ° C, preferably around 0 to 100 ° C. Generally, the reaction is completed in about 5 minutes to 30 hours. The condensing agent and the carboxylic acid (18 ') may be used in an amount of at least about equimolar amount, preferably about equimolar to 2-fold molar amount, with respect to the amine (1c').

  The reaction of compound (1c ′) with compound (19 ′) is carried out under the same reaction conditions as the reaction of compound (15 ′) with compound (16 ′) or (17 ′) in the aforementioned Reaction scheme-28. be able to.

[Wherein, R ^1a , X, n, m, W, R ^{7a ′} , R ^{9 ′} , R ^{10 ′} and o are the same as the above]. R ^{6b ′} represents a C1-6 alkoxycarbonyl group. The dotted line on the piperidine ring indicates that it may be a double bond. When the dotted line is a double bond, the group R ^{6b '} , a COOH group or a group -CONR ^9' R ^{10 '} is substituted. ]
Compound (21 ′) is produced by hydrolyzing compound (20 ′).

  The hydrolysis reaction is carried out in the presence of an acid or a basic compound in a suitable solvent or in the absence of a solvent.

  As the solvent to be used, for example, lower alcohols such as water, methanol, ethanol, isopropanol and tert-butanol, ketones such as acetone and methyl ethyl ketone, ethers such as diethyl ether, dioxane, tetrahydrofuran, monoglyme and diglyme, acetic acid, Fatty acids such as formic acid, esters such as methyl acetate and ethyl acetate, halogenated hydrocarbons such as chloroform, dichloromethane, dichloroethane and carbon tetrachloride, dimethyl sulfoxide, N, N-dimethylformamide, hexamethyl phosphate triamide or a mixture thereof A solvent etc. can be mentioned.

  Examples of the acid include mineral acids such as hydrochloric acid, sulfuric acid and hydrobromic acid; and organic acids such as sulfonic acids such as formic acid, acetic acid, trifluoroacetic acid and P-toluenesulfonic acid.

  Examples of the basic compound include carbonates such as sodium carbonate, potassium carbonate, sodium hydrogencarbonate and potassium hydrogencarbonate, and metal hydroxides such as sodium hydroxide, potassium hydroxide, calcium hydroxide and lithium hydroxide. be able to.

  The acid or basic compound is used at least equimolar, preferably equimolar to 10-fold molar, relative to compound (20 '), but may be used as a reaction solvent in a large excess.

  The reaction suitably proceeds usually at about 0 to 200 ° C., preferably at about 0 to 150 ° C., and is generally completed in about 10 minutes to 30 hours.

  After the above hydrolysis treatment, the reaction may be carried out usually in the presence of a basic compound in a suitable solvent to complete the reaction, preferably at about 0 to 100 ° C., preferably at about room temperature to 70 ° C., for about 1 to 30 minutes. Good. As the solvent and the basic compound used here, among the reactions of the compound (1c ′) and the compound (18 ′) in the above-mentioned reaction scheme-29, an amine (1c) can be added to the carboxylic acid halide of the method (d). Any solvent and basic compound used in the reaction method can be used.

  The reaction of compound (21 ') with compound (22') is carried out under the same reaction conditions as the reaction of compound (1c ') with compound (18') in the aforementioned Reaction scheme-29. However, the amount used was that the reaction formula-10 converted the amount used of the carboxylic acid (18 ') to the amine (1c'), but in the reaction, the amine to the carboxylic acid (18 ') Convert the used amount of (22 ').

[Wherein, R ^1a , n, X, m, W, o, X ² , R ^{4 ′} and R ^{5 ′} are as defined above. ]
The reaction of compound (1i ′) with compound (23 ′) is carried out under the same reaction conditions as the reaction of compound (1c ′) with compound (17 ′) in the aforementioned Reaction scheme-29.

[Wherein, R ^1a , n, R ^{18 ′} , X, m, W, o, R ^{4 ′} and X ² are the same as the above].

R ^{6aa ′} represents a C1-6 alkoxycarbonyl group.

R ^{6bb ′} is a C1 to 6 alkyl group; a phenyl group (on a phenyl ring, a C1 to 4 alkylenedioxy group, a cyano group, a nitro group, an amino group which may have a C1 to 6 alkyl group as a substituent, Amino-substituted sulfonyl group which may have a C1-6 alkyl group as a substituent, C1-6 alkoxycarbonyl group, C1-6 alkylthio group, phenoxy group, phenyl C1-6 alkoxy group, pyrrolidinyl group [in the pyrrolidine ring, At least one oxo group may be substituted], imidazolyl group, isoxazolyl group, oxazolyl group, phenyl C1-6 alkyl group, phenyl group, amino C1 having a C1-6 alkyl group as a substituent 6 alkyl group, pyrrolidinyl C1-6 alkoxy group, halogen atom, halogen-substituted or unsubstituted C1 6 alkyl group and at least one group selected from the group consisting of halogen substituted or unsubstituted C1-6 alkoxy group may be substituted; phenyl C1-6 alkoxycarbonyl group (on the phenyl ring, At least one selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted; benzofuryl C1 6 alkyl group (on the benzofuran ring, at least one of a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group as a substituent A species may be substituted); benzofuryl C1-6 alkenyl group (on the benzothiazole ring, a halogen atom, halogen At least one of a group selected from the group consisting of a substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted; At least one of a group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group is substituted on the phenyl ring Thiazolyl C.sub.1-6 alkyl group (on the thiazolyl ring, at least one phenyl group [on the phenyl ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted At least one of a group selected from the group consisting of a C1-6 alkoxy group may be substituted] may be substituted); A phenyl group (on the phenyl ring, a phenyl group [on the phenyl ring, selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group. Group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C.sub.1-6 alkyl group and a halogen-substituted or unsubstituted C.sub.1-6 alkoxy group; At least one type may be substituted); pyridyl C1-6 alkyl group [in which at least one phenyl group (a halogen atom, halogen-substituted or unsubstituted C1-6 on a phenyl ring, is substituted on the pyridine ring At least one of a group selected from the group consisting of an alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted C1-6 alkoxycarbonyl group; benzothienyl group; benzothienyl C1-6 alkyl group (at least one halogen atom may be substituted on the benzothiophene ring); indolyl C1-6 alkyl group (On the indole ring, at least one of a group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group is substituted 4H-1,3-benzodioxynyl group (at least one halogen atom may be substituted on the 4H-1,3-benzodioxin ring); naphthyl group; quinolyl group; A benzothiazolyl group (on the benzothiazole ring, at least one C1-6 alkyl group may be substituted); 2,3-dihydro-1H- (Optionally substituted at least one oxo group on 2,3-dihydro-1H-indane ring); 9H-fluorenyl group or phenyl C2-6 alkenyl group (on phenyl ring) And at least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted).

R ^{6c ′} is a benzoyl group (on the phenyl ring, at least one group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group 1 is optionally substituted).

R ^{6d ′} is a hydrogen atom, a phenyl group (on the phenyl ring [a phenyl group on the phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 And at least one group selected from the group consisting of alkoxy groups may be substituted], a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group At least one group selected from the group consisting of: a benzofuryl C.sub.1-6 alkyl group (on the benzofuran ring, a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted Or at least one group selected from the group consisting of unsubstituted C1-6 alkoxy groups may be substituted); benzofuryl group (the said benzofuran At least one selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted on the ring Phenoxy C1-6 alkyl group (on the phenyl ring, a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1-6 alkoxy group At least one type may be substituted); thiazolyl C1-6 alkyl group (on the thiazol ring, at least one phenyl group [on a phenyl ring, a halogen atom, halogen substituted or unsubstituted C1 to C6; At least one of a group selected from the group consisting of an alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted Thiazolyl group (at least one phenyl group on the thiazole ring [a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-on the phenyl ring A group selected from the group consisting of 6 alkoxy groups may be substituted by at least one group], phenyl C.sub.1-6 alkyl group (on phenyl ring, phenyl group [phenyl ring on phenyl ring; And at least one of a group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group may be substituted], At least at least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group Species may be substituted); pyridyl C1-6 alkyl group [wherein at least one phenyl group on the pyridine ring (on the phenyl ring a halogen atom, halogen substituted or unsubstituted C1-6 alkyl group And at least one of a group selected from the group consisting of halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted); benzothienyl C1-6 alkyl group (benzo At least one halogen atom may be substituted on the thiophene ring); indolyl C1-6 alkyl group (on indole ring, a halogen atom, halogen substituted or unsubstituted C1-6 alkyl group and halogen) At least one of a group selected from the group consisting of a substituted or unsubstituted C1-6 alkoxy group may be substituted); a pyridyl group [on a pyridine ring At least one phenyl group (on the phenyl ring, at least one group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group. At least one halogen atom may be substituted on the benzothiophene ring) or an indolyl group (indole ring) At least one group selected from the group consisting of a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group may be substituted on the above) Indicates

R ^{6e ′} is a phenyl group (on the phenyl ring, at least one group selected from the group consisting of a halogen atom, a halogen substituted or unsubstituted C.sub.1-6 alkyl group and a halogen substituted or unsubstituted C.sub.1-6 alkoxy group 1 is optionally substituted).

The total carbon number of the group -CHR ^{18 '} R ^{6b' in} the general formula (1o ') does not exceed 6. ]
The reaction for converting the compound (1k ′) to the compound (1l ′) is carried out under the same reaction conditions as the reaction for converting the compound (20 ′) to the compound (21 ′) in the aforementioned Reaction scheme-30.

  The reaction of compound (11 ') with compound (24') is carried out under the same reaction conditions as the reaction of compound (1c ') with compound (17') in the aforementioned Reaction scheme-29.

    The reaction of compound (11 ') with compound (25') is carried out under the same reaction conditions as the reaction of compound (1c ') with compound (18') in the aforementioned Reaction scheme-29.

    The reaction of compound (11 ') with compound (26') is carried out under the same reaction conditions as the reaction of compound (1c ') with compound (16') in the aforementioned Reaction scheme-29.

    The reaction of compound (11 ') with compound (27') is carried out under the same reaction conditions as the reaction of compound (1c ') with compound (19') in the aforementioned Reaction scheme-29.

[Wherein, R ^1a , n, X, m, W, o and R ^{4 ′} are as defined above. R ^{6f ′} is a C1-6 alkyl group or a phenyl C1-6 alkyl group (on the phenyl ring, a halogen atom, a halogen-substituted or unsubstituted C1-6 alkyl group and a halogen-substituted or unsubstituted C1-6 alkoxy group And at least one of the groups selected from the group consisting of ]
The reaction of compound (1q ′) with compound (26 ′) is carried out in the presence of a condensing agent in a suitable solvent.

  As the solvent used here, among the reactions of the compound (1c ′) and the compound (18 ′) in the above-mentioned reaction scheme-29, the carboxylic acid halide of the method (ii) is reacted with the amine (1c ′). Any of the solvents used in the process can be used.

  As a condensing agent, N, N'- carbonyl diimidazole etc. can be mentioned, for example. The amount of the compound (26 ') and the condensing agent to be used is at least 1 mol, preferably about 1 to 2 mol, per 1 mol of compound (1q'). The reaction is completed generally at 0 to 150 ° C., preferably at about 0 to 100 ° C., for about 1 to 30 hours.

[Wherein, R ^1a , n, X, m, W, o, R ^{9 ′} and R ^{10 ′} are as defined above. ]
The reaction of compound (27 ′) with compound (28 ′) is carried out under the same reaction conditions as the reaction of compound (1c ′) with compound (16 ′) in the aforementioned Reaction scheme-29.

[Wherein, R ^1a , n, X, m, W, o, R ^{7a ′} and R ^{10a ′} are as defined above. Two W in the general formulas (1t ') to (1v') may be the same or different. R ^{9f ′} represents a C1-6 alkoxycarbonyl group. The dotted line on the piperidine ring indicates that it may be a double bond. When the dotted line is a double bond, the group-(W) oNR ^{9f '} R ^10a' , the group-(W) oNHR ^{10a '} or the group-(W) oNR ^10a' (COOR ^{9g '} ) is substituted. R ^{9g ′} is a C1-6 alkyl group or a phenyl C1-6 alkyl group (on the phenyl ring, a halogen atom as a substituent, a halogen substituted or unsubstituted C1-6 alkyl group and a halogen substituted or unsubstituted C1 At least one group selected from the group consisting of 6 alkoxy groups may be substituted). ]
The reaction for converting the compound (1t ′) to the compound (1u ′) is carried out under the same reaction conditions as the reaction for converting the compound (20 ′) to the compound (21 ′) in the aforementioned Reaction scheme-30.

  The reaction of compound (1u ') with compound (29') is carried out under the same reaction conditions as the reaction of compound (1q ') with compound (26') in the aforementioned Reaction scheme-33.

  The starting material compound (14 ') of Reaction scheme-28 and the starting material compound (20') of Reaction scheme-30 are novel compounds. These compounds can be easily produced, for example, by using the corresponding starting materials and following the methods shown in the reaction scheme formulas 1 to 2.

  The compound (final compound) represented by the general formula (1) of the present invention and the intermediates obtained in the above reaction schemes include stereoisomers and optical isomers.

  Each target compound obtained in each reaction scheme shown above is obtained by, for example, cooling the reaction mixture, and then separating the crude reaction product by an isolation operation such as filtration, concentration, extraction, etc. It can be isolated and purified from the reaction mixture by ordinary purification operation such as crystallization.

  The compounds of the present invention include pharmaceutically acceptable salts. Such salts include, for example, mineral acid salts such as hydrochloride, hydrobromide, nitrate, sulfate, phosphate, etc., methanesulfonate, p-toluenesulfonate, acetate, citrate, tartaric acid And salts of organic acids such as maleates, fumarates, malates and lactates.

  Next, a medical preparation containing the compound of the present invention as an active ingredient will be described.

  The above-mentioned medical preparation is prepared by formulating the compound of the present invention in the form of a usual medical preparation, and a filler, an extender, a binder, a moisturizer, a disintegrant, a surface active agent and a lubricant which are usually used. Etc. are prepared using a diluent or excipient such as

  Such a medical preparation can be selected from various forms according to the therapeutic purpose, and representative ones are tablets, pills, powders, solutions, suspensions, emulsions, granules, capsules, sitting Agents, injections (solutions, suspensions etc.) and the like.

  As a carrier used when forming in the form of a tablet, known ones can be widely used, for example, excipients such as lactose, sucrose, sodium chloride, glucose, urea, starch, calcium carbonate, kaolin, crystalline cellulose, etc. Binders such as water, ethanol, propanol, simple syrup, glucose solution, starch solution, gelatin solution, carboxymethylcellulose, shellac, methylcellulose, potassium phosphate, polyvinylpyrrolidone etc., dry starch, sodium alginate, agar powder, laminaran powder, hydrogen carbonate Sodium, calcium carbonate, polyoxyethylene sorbitan fatty acid esters, sodium lauryl sulfate, monoglyceride of stearic acid, starch, disintegrating agent such as lactose, sucrose, disintegrating agent such as stearin, cocoa butter, hydrogenated oil, etc. quaternary ammonium , Absorption accelerators such as sodium lauryl sulfate, moisturizers such as glycerin and starch, adsorbents such as starch, lactose, kaolin, bentonite and colloidal silicic acid, purified talc, stearate, boric acid powder, polyethylene glycol etc. Lubricants and the like.

  Furthermore, the tablets can be tablets, which are coated with conventional tablets as required, for example, sugar coating, gelatin coated tablet, enteric coated tablet, film-coated tablet or double tablet, multilayer tablet.

  As a carrier used when forming into a pill form, known ones can be widely used. For example, an excipient such as glucose, lactose, starch, cocoa butter, hydrogenated vegetable oil, kaolin, talc, gum arabic powder, Examples thereof include binders such as tragacanth powder, gelatin and ethanol, and disintegrators such as laminaran and agar.

  As a carrier used when forming into a suppository form, publicly known ones can be widely used and, for example, polyethylene glycol, cacao butter, higher alcohol, esters of higher alcohol, gelatin, semi-synthetic glyceride and the like can be mentioned.

  When prepared as an injection, solutions, emulsions and suspensions are preferably sterile and isotonic with blood. As a diluent used when forming into the form of these solutions, emulsions and suspensions, those widely known can be used, for example, water, ethanol, propylene glycol, ethoxy And isostearyl alcohol, polyoxylated isostearyl alcohol, polyoxyethylene sorbetan fatty acid esters and the like. In this case, a sufficient amount of sodium chloride, glucose or glycerin may be contained in the pharmaceutical preparation to prepare an isotonic solution, and a common solubilizer, buffer, soothing agent, etc. Further, if necessary, colorants, preservatives, flavors, flavors, sweeteners and the like and other medicines may be contained.

  The amount of the compound of the present invention contained in the medical preparation is not particularly limited and can be appropriately selected from a wide range, but usually, it is preferable to contain 1 to 70% by weight of the compound of the present invention in the medical preparation .

  The administration method of the medical preparation according to the present invention is not particularly limited, and administration is carried out according to various preparation forms, patient's age, sex, disease state, and other conditions. For example, tablets, pills, solutions, suspensions, emulsions, granules and capsules are orally administered. In the case of injections, they may be administered intravenously alone or in combination with ordinary fluid replacements such as glucose and amino acids, and further, if necessary, alone, intramuscularly, intracutaneously, subcutaneously or intraperitoneally. It can be administered. In the case of suppositories, it is administered rectally.

  The dosage of the above-mentioned medical preparation may be appropriately selected according to the dosage, patient's age, sex, degree of disease and other conditions, and usually 0.01 to 100 mg, preferably 1 kg of body weight per day. 0.1 to 50 mg may be administered once to several times.

  Since the above dose varies under various conditions, a dose smaller than the above range may be sufficient, or a dose exceeding the above range may be required.

  The compound of the present invention is particularly effective against Mycobacterium tuberculosis (Mycobacterium, atypical Mycobacterium) such as acid-fast bacteria. The compounds of the present invention have excellent effects on multidrug-resistant Mycobacterium tuberculosis. The compound of the present invention has an antibacterial action against anaerobic bacteria.

  The compounds of the present invention not only show the above activity in vitro, but also exhibit the above activity upon oral administration.

  The compound of the present invention does not induce diarrhea as seen in known antibacterial agents having a broad spectrum against general bacteria such as gram positive bacteria and gram negative bacteria, and side effects as compared with existing drugs Because it is small, it can be a medical preparation that can be taken for a long time.

  The compound of the present invention can be well distributed to the lung tissue, which is the main infected organ of acid-fast bacteria infection, and has high properties such as long duration of efficacy and excellent safety. Therapeutic effect can be expected.

  The compound of the present invention is more effective against intracellular parasites such as human-derived macrophage infective tubercle bacillus and the like than existing antituberculosis agents, and therefore, the relapse rate of tuberculosis can be reduced, and thus the short-term It enables chemotherapy and is expected to be used as a mainstay of preventive medications that are being implemented because HIV / TB mixed infection is a serious problem.

  Hereinafter, formulation examples, reference examples, examples and test examples are listed.

Formulation example 1
100 g of the compound of the present invention, 40 g of Avicel (trade name, manufactured by Asahi Kasei Co., Ltd.), 30 g of corn starch and 2 g of magnesium stearate were mixed and polished, and then tableted with sugar coating R10 mm.

  The obtained tablet is coated with a film coating agent consisting of 10 g of TC-5 (trade name, manufactured by Shin-Etsu Chemical Co., Ltd., hydroxypropyl methylcellulose), 3 g of polyethylene glycol-6000, 40 g of castor oil and an appropriate amount of ethanol, Film-coated tablets of the above composition were produced.

Reference Example 1
Preparation of 4- (2-oxopropyl) piperazine-1-carboxylic acid benzyl ester Potassium carbonate (1.27 g) in a solution of piperazine-1-carboxylic acid benzyl ester (2.03 g, 9.22 mmol) in acetonitrile (20 ml) (9.22 mmol), N-ethyldiisopropylamine (0.80 ml, 4.61 mmol) and chloroacetone (1.22 ml, 13.83 mmol) were added and the mixture was heated under reflux for 2 hours. The insolubles were filtered and washed with ethyl acetate. The mother liquor and washings were combined and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride / methanol = 100/1) to give 4- (2-oxopropyl) piperazine-1-carboxylic acid benzyl ester (2.24 g, yield 88%) as a slightly yellow liquid. Got).
¹ H-NMR (CDCl ₃ ) δ ppm:
2.15 (3H, s), 2.35 to 2.50 (4H, m), 3.21 (2H, s), 3.50 to 3.62 (4H, m), 5.13 (2H, 2) s), 7.27-7. 42 (5 H, m).

Reference Example 2
Preparation of 4- (3-oxobutyl) piperazine-1-carboxylic acid tert-butyl ester To a mixture of methyl vinyl ketone (2.3 g, 32.9 mmol) and THF (25 ml) was added piperazine-1 under ice cooling. A solution of carboxylic acid tert-butyl ester (6 g, 32.3 mmol) in THF (50 ml) was slowly added dropwise and stirred at room temperature for 3 days. The reaction solution is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (methylene chloride / methanol = 20/1) to obtain 4- (3-oxobutyl) piperazine-1-carboxylic acid tert- of a slightly yellow oil. The butyl ester (7.2 g, yield 87%) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.46 (9H, s), 2.17 (3H, s), 2.30-2.42 (4H, m), 2.53-2.70 (4H, m), 3.33-3. 47 (4H, m).

  The compounds of Reference Example 3 to Reference Example 10 were produced in the same manner as in Reference Example 1 using the corresponding starting materials.

Reference Example 3
1- [4- (4-trifluoromethylphenyl) piperazin-1-yl] propan-2-one yield 99%
¹ H-NMR (CDCl ₃ ) δ ppm:
2.18 (3H, s), 2.63-2.68 (4H, m), 3.27 (2H, s), 3.30-3.45 (4H, m), 6.92 (2H, 2H, s) d, J = 8.7 Hz), 7.48 (2 H, d, J = 8.7 Hz).

Reference Example 4
1- (4-phenylpiperazin-1-yl) propan-2-one yield 95%
¹ H-NMR (CDCl ₃ ) δ ppm:
2.19 (3 H, s), 2.65-2.70 (4 H, m), 3. 27-3. 22 (6 H, m), 6. 97-7. 01 (2 H, m), 7. 24-7.31 (1 H, m), 7.37-7. 43 (2 H, m).

Reference Example 5
1- [4- (4-chlorophenyl) piperazin-1-yl] propan-2-one yield 99%
¹ H-NMR (CDCl ₃ ) δ ppm:
2.17 (3H, s), 2.63-2.67 (4H, m), 3.18-3.23 (4H, m), 3.26 (2H, s), 6.80-6. 87 (2H, m), 7.17-7. 23 (2H, m).

Reference Example 6
1- [4- (4-trifluoromethoxyphenyl) piperazin-1-yl] propan-2-one yield 100%
¹ H-NMR (CDCl ₃ ) δ ppm:
2.18 (3H, s), 2.63-2.68 (4H, m), 3.20-3. 25 (4H, m), 3.26 (2H, s), 6.85-6. 92 (2H, m), 7.09-7. 13 (2H, m).

Reference Example 7
1- [4- (2-pyridyl) piperazin-1-yl] propan-2-one yield 97%
¹ H-NMR (CDCl ₃ ) δ ppm:
2.19 (3H, s), 2.58-2.63 (4H, m), 3.25 (2H, s), 3.57-3.62 (4H, m), 6.60-6. 66 (2H, m), 7.44-7.51 (1 H, m), 8.17-8.20 (1 H, m).

Reference Example 8
1- [4- (2-Pyrimidyl) piperazin-1-yl] propan-2-one yield 88%
¹ H-NMR (CDCl ₃ ) δ ppm:
2.19 (3 H, s), 2.53-2.57 (4 H, m), 3. 25 (2 H, s), 3.86-3.90 (4 H, m), 6.49 (1 H, 1 H, s) t, J = 4.8 Hz), 8.30 (2 H, d, J = 4.8 Hz).

Reference Example 9
N- [1- (2-Oxopropyl) piperidin-4-yl] -N-methyl-carbamic acid tert-butyl ester yield 79%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.46 (9 H, s), 1.57-1.63 (2 H, m), 1. 70-1.91 (2 H, m), 2.04-2.18 (2 H, m), 14 (3 H, s), 2.71-2. 74 (1 H, m), 2. 74 (3 H, s), 2. 90-2. 95 (2 H, m), 3. 19 (2 H, s) .

Reference Example 10
4- (2-Oxopropyl) homopiperazine-1-carboxylic acid tert-butyl ester yield 58%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.46 (9H, s), 1.75 to 1.93 (2H, m), 2.14 (3H, s), 2.64 to 2.76 (4H, m), 3.32 (2H, 2) s), 3.38-3.58 (4 H, m).

Reference Example 11
Preparation of 1- (4-trifluoromethylbenzoyl) -4-hydroxypiperidine To a mixture of 4-hydroxypiperidine (1 g, 9.89 mmol), triethylamine (1.7 ml, 11.9 mmol) and methylene chloride (20 ml) Under ice-cooling, 4- (trifluoromethyl) benzoyl chloride (1.5 ml, 9.89 mmol) was added, and the mixture was stirred at room temperature for 30 minutes. The reaction solution was washed sequentially with water, saturated aqueous sodium bicarbonate solution and saturated brine, and dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (n-hexane / acetone = 2/1) to give 1- (4-trifluoromethylbenzoyl) -4-hydroxypiperidine (2.07 g, yield 77%) of white powdery crystals. I got
¹ H-NMR (CDCl ₃ ) δ ppm:
1.36-2.07 (4H, m), 3.07-3.70 (3H, m), 3.91-4.32 (2H, m), 7.51 (2H, d, J = 8 .0 Hz), 7.68 (2 H, d, J = 8.0 Hz).

  The compound of Reference Example 12 was produced in the same manner as in Reference Example 11 using the corresponding starting materials.

Reference Example 12
1- (4-Trifluoromethoxybenzoyl) -4-hydroxypiperidine white powder crystal, 100% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
1.34-2.07 (4H, m), 3.09-3.80 (3H, m), 3.9 1-4. 32 (2H, m), 7. 25 (2H, d, J = 7 .9 Hz), 7.45 (2 H, d, J = 7.9 Hz).

Reference Example 13
Preparation of 1- [2- (Tetrahydropyran-2-yloxy) ethyl] -4- (4-trifluoromethylphenoxy) piperidine 4- (4-Trifluoromethylphenoxy) piperidine (1.87 g, 7.63 mmol) , 2- (2-bromoethoxy) tetrahydropyran (1.75 g, 8.4 mmol), potassium carbonate (1.16 g, 8.38 mmol), sodium iodide (1.2 g, 8.01 mmol) and DMF The mixture of (30 ml) was stirred at 100 ° C. for 1 hour. The reaction was allowed to warm to room temperature, poured into water and extracted twice with ethyl acetate. The organic phases were combined, washed twice with water, then washed with saturated brine and dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / methanol = 50/1) to give 1- [2- (tetrahydropyran-2-yloxy) ethyl] -4- (4-trifluoromethylphenoxy) piperidine as a colorless oil. (1.69 g, 59% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.39-2.12 (10H, m), 2.36-2.53 (2H, m), 2.68 (2H, t, J = 6.1 Hz), 2.71-2.92 (2H) , M), 3.43-3.63 (2H, m), 3.78-3.94 (2H, m), 4.31-4.47 (1H, m), 4.57-4.67 (1 H, m), 6.96 (2 H, d, J = 8.7 Hz), 7.52 (2 H, d, J = 8.7 Hz).

Reference Example 14
Preparation of 2- [4- (4-trifluoromethylphenoxy) piperidin-1-yl] ethanol 1- [2- (tetrahydropyran-2-yloxy) ethyl] -4- (4-tri) prepared in Reference Example 13 A mixture of fluoromethyl phenoxy) piperidine (1.69 g, 4.53 mmol), pyridinium p-toluenesulfonate (114 mg, 0.45 mmol) and ethanol (50 ml) was stirred at 60-70 ° C. for 6 hours. The reaction solution was returned to room temperature and concentrated under reduced pressure. To the residue was added 10% caustic soda and extracted with methylene chloride. The extract was washed with saturated brine and dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride / methanol = 50/1) to give 2- [4- (4-trifluoromethylphenoxy) piperidin-1-yl] ethanol (1.19 g, yield) as a colorless oil. 91%).
¹ H-NMR (CDCl ₃ ) δ ppm:
1.73-2.10 (4H, m), 2.31-2.47 (2H, m), 2.58 (2H, t, J = 5.5 Hz), 2.69-3.00 (3H) , M), 3.63 (2H, t, J = 5.5 Hz), 4.33-4.48 (1 H, m), 6.95 (2 H, d, J = 8.6 Hz), 7.53 (2H, d, J = 8.6 Hz).

Reference Example 15
Preparation of 2- [2- (4-Trifluoromethylphenoxy) ethoxy] tetrahydropyran 4-Hydroxybenzotrifluoride (2.08 g, 12.83 mmol), 2- (2-bromoethoxy) tetrahydropyran (3 g, 14 A mixture of .11 mmol), potassium carbonate (1.95 g, 14.11 mmol), sodium iodide (2 g, 13.47 mmol) and DMF (15 ml) was stirred at 100 ° C. for 3 hours. The reaction was allowed to warm to room temperature, poured into water and extracted twice with ethyl acetate. The organic phases were combined, washed twice with water, then washed with saturated brine and dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane / ethyl acetate = 1/1) to give 2- [2- (4-trifluoromethylphenoxy) ethoxy] tetrahydropyran (2.47 g, yield 66) as a colorless oil. %) Got.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.41-1.90 (6H, m), 3.45-3.66 (1H, m), 3.76-3.96 (2H, m), 4.02-4.24 (3H, m) , 4.63-4.76 (1 H, m), 6.98 (2 H, d, J = 8.6 Hz), 7.53 (2 H, d, J = 8.6 Hz).

Reference Example 16
Preparation of 2- (4-trifluoromethylphenoxy) ethanol Reference was made using 2- [2- (4-trifluoromethylphenoxy) ethoxy] tetrahydropyran (2.47 g, 8.51 mmol) prepared in Reference Example 15 In the same manner as in Example 14, 2- (4-trifluoromethylphenoxy) ethanol (1.32 g, yield 79%) of white powdery crystals was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
3.88-4.14 (4H, m), 6.98 (2H, d, J = 8.6 Hz), 7.55 (2 H, d, J = 8.6 Hz).

Reference Example 17
Preparation of 1- [2- (tetrahydropyran-2-yloxy) ethyl] -4- (4-trifluoromethoxyphenyl) -1,2,3,6-tetrahydropyridine 4- (4-trifluoromethoxyphenyl)- Analogously to Reference Example 15 using 1,2,3,6-tetrahydropyridine monohydrochloride (680 mg, 2.43 mmol) and 2- (2-bromoethoxy) tetrahydropyran (610 mg, 2.92 mmol) , 1- [2- (Tetrahydropyran-2-yloxy) ethyl] -4- (4-trifluoromethoxyphenyl) -1,2,3,6-tetrahydropyridine (425 mg, yield 47%) I got
¹ H-NMR (CDCl ₃ ) δ ppm:
1.41-1.92 (6H, m), 2.45-2.59 (2H, m), 2.67-2.86 (4H, m), 3.18-3. 21 (2H, m) ), 3.43-3.65 (2H, m), 3.80-4.00 (2H, m), 4.55-4.65 (1H, m), 5.98-6.10 (1H) , M), 7.15 (2 H, dd, J = 2.1 Hz, 8.8 Hz), 7.38 (2 H, dd, J = 2.1 Hz, 8.8 Hz).

Reference Example 18
Preparation of 2- [4- (4-trifluoromethoxyphenyl) -1,2,3,6-tetrahydropyridin-1-yl] ethanol 1- [2- (tetrahydropyran-2-yloxy) prepared in Reference Example 17 In the same manner as in Reference Example 14 using ethyl) -4- (4-trifluoromethoxyphenyl) -1,2,3,6-tetrahydropyridine (425 mg, 1.14 mmol), [4- (4-Trifluoromethoxyphenyl) -1,2,3,6-tetrahydropyridin-1-yl] ethanol (222 mg, yield 68%) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
2.47-2.59 (2H, m), 2.68 (2H, t, J = 5.5 Hz), 2.79 (2H, t, J = 5.5 Hz), 3.16-3.25 (2H, m), 3.70 (2H, t, J = 5.5 Hz), 6.00-6.10 (1 H, m), 7.17 (2 H, dd, J = 2.1 Hz, 6. 7 Hz), 7.40 (2 H, dd, J = 2.1 Hz, 6.7 Hz).

Reference Example 19
Preparation of 3- (4-Trifluoromethylphenyl) -2-propyn-1-ol 4-Bromobenzotrifluoride (6.5 g, 28.89 mmol), propargyl alcohol (2.35 ml, 40.45 mmol), Triethylamine (5.64 ml, 40.45 mmol), triphenylphosphine (230 mg, 0.87 mmol), cuprous iodide (110 mg, 0.58 mmol), dichlorobis (triphenylphosphine) palladium (210 mg, 0. 1). A mixture of 29 mmol) and toluene (100 ml) was stirred at 100 ° C. for 2 hours under a nitrogen atmosphere. The reaction solution was returned to room temperature and filtered through celite. The filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 9/1) to give 3- (4-trifluoromethylphenyl) -2-propyne-1 as a light tea oil. -All (3.47 g, 60% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
4.52 (2H, d, J = 6.2 Hz), 7.53 (2 H, d, J = 8.7 Hz), 7.58 (2 H, d, J = 8.7 Hz).

Reference Example 20
Preparation of 2- [N-methyl- (4-trifluoromethoxyphenyl) amino] ethanol N-methyl- (4-trifluoromethoxyphenyl) amine (4.83 g, 24.24 mmol), 2- (2-bromo) A mixture of (ethoxy) tetrahydropyran (6.1 g, 29.03 mmol), potassium carbonate (3.84 g, 27.76 mmol) and DMF (20 ml) was stirred at 100 ° C. for 5 hours. The reaction was allowed to warm to room temperature, poured into water and extracted twice with ethyl acetate. The organic phases were combined, washed twice with water, then washed with saturated brine and dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride / ethyl acetate = 20/1) to give 2- [N-methyl- (4-trifluoromethoxyphenyl) amino] ethanol (3.1 g, yield as slightly yellow oil) 53%).
¹ H-NMR (CDCl ₃ ) δ ppm:
2.96 (3 H, s), 3.46 (2 H, t, J = 5.7 Hz), 3.81 (2 H, q, J = 5.7 Hz), 6.74 (2 H, d, J = 8) .7 Hz), 7.08 (2 H, d, J = 8.7 Hz).

Reference Example 21
Preparation of 8- (4-Trifluoromethoxyphenyl) -1,4-dioxa-8-azaspiro [4.5] decane 1-Bromo-4- (trifluoromethoxy) benzene (6.3 g, 26.14 mmol) 1,4-dioxa-8-azaspiro [4,5] decane (3.35 ml, 26.14 mmol), palladium acetate (60 mg, 0.26 mmol), (S)-(-)-2,2- A mixture of bis (diphenylphosphino) -1,1′-binaphthyl (BINAP) (244 mg, 0.39 mmol), tert-butoxy sodium (3.77 g, 39.23 mmol) and toluene (50 ml) at 80 ° C. The mixture was stirred for 1 hour. The reaction solution was returned to room temperature, 50 ml of ethyl acetate was added, and the mixture was filtered. The filtrate was washed with water, then with saturated brine, and dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / methanol = 50/1) to give 8- (4-trifluoromethoxyphenyl) -1,4-dioxa-8-azaspiro [4.5] decane as slightly yellow powder. (6.54 g, 83% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.83 (4 H, t, J = 5.8 Hz), 3.31 (4 H, t, J = 5.8 Hz), 3.99 (4 H, s), 6. 90 (2 H, d, J = 8 .8 Hz), 7.09 (2 H, d, J = 8.8 Hz).

Reference Example 22
Preparation of 1- (4-trifluoromethoxyphenyl) piperidin-4-one 8- (4-trifluoromethoxyphenyl) -1,4-dioxa-8-azaspiro [4.5] decane prepared in Reference Example 21 A mixture of 1.23 g, 4.06 mmol), concentrated hydrochloric acid (5 ml), water (10 ml) and ethanol (30 ml) was heated to reflux for 5 hours. The reaction solution was returned to room temperature and concentrated under reduced pressure. To the residue was added 10% caustic soda and extracted with methylene chloride. After washing with water, it was washed with saturated brine and dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (n-hexane / ethyl acetate = 3/1) to give 1- (4-trifluoromethoxyphenyl) piperidin-4-one (848 mg, yield 81%) as a colorless oil. The
¹ H-NMR (CDCl ₃ ) δ ppm:
2.56 (4H, t, J = 6.2 Hz), 3.59 (4 H, t, J = 6.2 Hz), 6.94 (2 H, d, J = 8.5 Hz), 7.14 (2 H) , D, J = 8.5 Hz).

Reference Example 23
Preparation of 1- (4-Trifluoromethoxyphenyl) piperidin-4-ol 1- (4-Trifluoromethoxyphenyl) piperidin-4-one (1.11 g, 4.28 mmol) prepared in Reference Example 22 and methanol To a mixture of (30 ml) was added sodium borohydride (324 mg, 8.56 mmol) under ice-cooling, and stirred at the same temperature for 30 minutes. To the reaction solution was added 10% hydrochloric acid, and concentrated under reduced pressure. To the residue was added saturated aqueous sodium bicarbonate solution, and the mixture was extracted with methylene chloride. The extract solution was washed with water, then with saturated brine, and dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (n-hexane / ethyl acetate = 3/1) to give 1- (4-trifluoromethoxyphenyl) piperidin-4-ol (1.08 g, yield 97%) as a white powder. I got
¹ H-NMR (CDCl ₃ ) δ ppm:
1.59-1.76 (2H, m), 1.90-2.06 (2H, m), 2.82-2.98 (2H, m), 3.43-3.57 (2H, m) ), 3.75-3.91 (1 H, m), 6.89 (2 H, d, J = 7.1 Hz), 7.09 (2 H, d, J = 7.1 Hz).

  The compounds of Reference Example 24 and Reference Example 25 were produced in the same manner as in Reference Example 23.

Reference Example 24
1- (4-Trifluoromethylphenyl) piperidin-4-ol white powder, yield 76%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.53-1.71 (2H, m), 1.89-2.04 (2H, m), 2.91-3.11 (2H, m), 3.56-3.71 (2H, m) 3.80-4.00 (1 H, m), 6.93 (2 H, d, J = 8.7 Hz), 7.46 (2 H, d, J = 8.7 Hz).

Reference Example 25
1- (4-Methoxyphenyl) piperidine 4-ol white powder, 5% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
1.64-1.79 (2H, m), 1.92-2.08 (2H, m), 2.74-2.88 (2H, m), 3.32-3.47 (2H, m) ), 3.70-3.85 (4H, m), 6.84 (2H, dd, J = 2.4 Hz, 6.8 Hz), 6.93 (2 H, dd, J = 2.4 Hz, 6. 8 Hz).

Reference Example 26
Preparation of 1- (4-chlorophenyl) piperidin-4-ol 8- (4-chlorophenyl) -1,4-dioxa-8-azaspiro [4.5] decane (2.6 g, 10.25 mmol), concentrated hydrochloric acid A mixture of (12 ml), water (10 ml) and ethanol (50 ml) was heated to reflux for 5 hours. The reaction solution was returned to room temperature and concentrated under reduced pressure. To the residue was added 10% caustic soda and extracted with methylene chloride. After washing with water, it was washed with saturated brine and dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was dissolved in methanol (50 ml), sodium borohydride (388 mg, 10.25 mmol) was added under ice-cooling, and the mixture was stirred for 30 minutes at the same temperature. To the reaction solution was added 10% hydrochloric acid, and concentrated under reduced pressure. To the residue was added saturated aqueous sodium bicarbonate solution, and the mixture was extracted with methylene chloride. After washing with water, it was washed with saturated brine and dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (n-hexane / ethyl acetate = 3/1) to give 1- (4-chlorophenyl) piperidin-4-ol (1.73 g, yield 80%) of pale yellow powdery crystals. Obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.55-1.74 (2H, m), 1.89-2.08 (2H, m), 2.79-3.00 (2H, m), 3.43-3.57 (2H, m) ), 3.75-3.92 (1 H, br), 6.89 (2 H, d, J = 7.1 Hz), 7.09 (2 H, d, J = 7.1 Hz).

  The compound of Reference Example 27 was produced in the same manner as in Reference Example 26 using the corresponding starting materials.

Reference Example 27
1- (4-Fluorophenyl) piperidin-4-ol white powder, 66% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
1.57-1.79 (2H, m), 1.92-2.08 (2H, m), 2.75-2.92 (2H, m), 3.36-3.50 (2H, m) ), 3.74-3.89 (1 H, m), 6.77-7.00 (4 H, m).

Reference Example 28
Preparation of 4- [4- (tert-butyldimethylsiloxy) piperidin-1-yl] benzonitrile 4-Bromobenzonitrile (2.76 g, 15.16 mmol), 4- (tert-butyldimethylsiloxy) piperidine (2 .9 g, 13.79 mmol), palladium acetate (62 mg, 0.28 mmol), (S)-(-)-2,2'-bis (diphenylphosphino) -1,1'-binaphthyl (BINAP) ( A mixture of 258 mg, 0.41 mmol), sodium tert-butoxy (1.99 g, 20.68 mmol) and toluene (60 ml) was stirred at 80 ° C. for 1 hour. The reaction solution was returned to room temperature, 60 ml of ethyl acetate was added, and the mixture was filtered. The filtrate was washed with water, then with saturated brine, and dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (n-hexane / methylene chloride = 1/1) to give 4- [4- (tert-butyldimethylsiloxy) piperidin-1-yl] benzonitrile (2. 8 g (yield 66%) were obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
0.90 (9H, s), 1.50-1.69 (8H, m), 1.73-1.90 (2H, m), 3.18-3. 31 (2H, m), 50-3.65 (2H, m), 3.90-4.04 (1H, m), 6.85 (2H, d, J = 7.0 Hz), 7.47 (2H, d, J = 7) .0 Hz).

Reference Example 29
Preparation of 4- (4-hydroxypiperidin-1-yl) benzonitrile 4- [4- (tert-Butyldimethylsiloxy) piperidin-1-yl] benzonitrile (2.8 g, 8.85) prepared in Reference Example 28 A solution of 1 M tetra n-butylammonium fluoride in THF (10.6 ml, 10.2 mmol) was added to a mixture of mmol) and THF (30 ml) under ice-cooling, and the mixture was stirred at room temperature for 16 hours. The reaction solution was concentrated under reduced pressure. To the residue was added water and extracted twice with ethyl acetate. The organic phases were combined, washed with water, then with saturated brine, and dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (n-hexane / ethyl acetate = 1/2) to give 4- (4-hydroxypiperidin-1-yl) benzonitrile (1.52 g, yield 85%) as white powder crystals. I got
¹ H-NMR (CDCl ₃ ) δ ppm:
1.50 to 1.73 (2H, m), 1.90 to 2.04 (2H, m), 3.00 to 3.20 (2H, m), 3.59 to 3.76 (2H, m) ), 3.84-4.04 (1 H, m), 6.86 (2 H, dd, J = 2.0 Hz, 7.1 Hz), 7.48 (2 H, dd, J = 2.0 Hz, 7. 1 Hz).

Reference Example 30
Preparation of 1- (4-trifluoromethylphenyl) piperidine-4-carboxylic acid ethyl ester 4-bromobenzotrifluoride (3.15 g, 13.99 mmol) and ethyl isonipecotate (2.2 g, 13.99 mmol) In the same manner as in Reference Example 21, 1- (4-trifluoromethylphenyl) piperidine-4-carboxylic acid ethyl ester (3.18 g, yield 74%) of pale tea powder crystals was obtained using
¹ H-NMR (CDCl ₃ ) δ ppm:
1.27 (3 H, t, J = 7.2 Hz), 1.71-2.10 (4 H, m), 2.41-2. 55 (1 H, m), 2.82-2.98 (2 H) , M), 3.65-3.80 (2H, m), 4.16 (2H, q, J = 7.2 Hz), 6.92 (2H, d, J = 6.9 Hz), 7.63 (2H, d, J = 6.9 Hz).

Reference Example 31
Preparation of [1- (4-trifluoromethylphenyl) piperidin-4-yl] methanol: Lithium aluminum hydride (1.58 g, 41.64 mmol) was suspended in THF (30 ml), and cooled with ice under a nitrogen atmosphere. A solution of 1- (4-trifluoromethylphenyl) piperidine-4-carboxylic acid ethyl ester (3.18 g, 10.41 mmol) prepared in Reference Example 30 in THF (10 ml) was added dropwise. It stirred for 30 minutes under the same temperature. Water and 10% caustic soda were added to the reaction solution and filtered through celite. The filtrate was extracted twice with ethyl acetate. The organic phases were combined, washed with water, then with saturated brine, and dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to obtain [1- (4-trifluoromethylphenyl) piperidin-4-yl] methanol (2.64 g, yield 98%) as a slightly yellow oil.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.31-1.47 (2H, m), 1.61-1.90 (3H, m), 2.74-2.90 (2H, m), 3.45-3.61 (2H, m) ), 3.83 (2H, d, J = 12.6 Hz), 6.92 (2H, d, J = 8.8 Hz), 7.46 (2H, d, J = 8.8 Hz).

Reference Example 32
Preparation of 1- (4-Trifluoromethoxybenzyl) piperidin-4-ol 4- (Trifluoromethoxy) benzaldehyde (1 g, 5.26 mmol), 4-hydroxypiperidine (798 mg, 7.89 mmol) and acetonitrile (20 ml) Sodium triacetoxyborohydride (1.67 g, 7.89 mmol) was added to the mixture under ice cooling, and the mixture was stirred at the same temperature for 30 minutes and then overnight at room temperature. The reaction solution was poured into 7.5% sodium bicarbonate water and extracted twice with ethyl acetate. The organic phases were combined, washed with water, then with saturated brine, and dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride / methanol = 10/1) to give 1- (4-trifluoromethoxybenzyl) piperidin-4-ol (1.21 g, yield 84%) as a slightly yellow oil. Obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.50 to 1.74 (2H, m), 1.80 to 1.98 (2H, m), 2.08 to 2.24 (2H, m), 2.63 to 2.84 (2H, m) ), 3.49 (2H, s), 3.61-3.80 (1H, m), 7.15 (2H, d, J = 8.5 Hz), 7. 34 (2H, d, J = 8) .5 Hz).

  The compounds of Reference Example 33 and Example 34 were produced in the same manner as in Reference Example 32.

Reference Example 33
1- (4-Chlorobenzyl) piperidin-4-ol white powder, yield 87%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.48-1.63 (2H, m), 1.76-1.91 (2H, m), 2.04-2.20 (2H, m), 2.61-2. 76 (2H, m) ), 3.45 (2H, s), 3.57 to 3.72 (1H, m), 7.24 (2H, d, J = 8.8 Hz), 7.28 (2 H, d, J = 8) .8 Hz).

Reference Example 34
1- (4-Trifluoromethylbenzyl) piperidin-4-ol white powder, yield 83%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.43-1.67 (2H, m), 1.80-1.94 (2H, m), 2.06-2.24 (2H, m), 2.63-2.78 (2H, m) ), 3.67 (2 H, s), 3.61-3. 72 (1 H, m), 7.44 (2 H, d, J = 8.0 Hz), 7.57 (2 H, d, J = 8 .0 Hz).

Reference Example 35
Preparation of (4-benzylpiperazin-1-yl) carbamic acid tert-butyl ester 4-benzylpiperazin-1-ylamine (36.03 g, 188 mmol) was dissolved in methanol (260 ml) and ice cooled. A solution of di-tert-butyl dicarbonate (61.66 g, 283 mmol) in methanol (100 ml) was added dropwise over 20 minutes. It returned to room temperature and stirred overnight. The reaction mixture was concentrated and then purified by silica gel column chromatography (n-hexane / acetone = 3/1). Isopropyl ether (IPE) (60 ml) and n-hexane (20 ml) were added to the obtained solid, and after stirring, it was filtered to obtain primary crystals. The mother liquor was concentrated, isopropyl ether (10 ml) and n-hexane (10 ml) were added, and after stirring, it was filtered to obtain secondary crystals. The primary crystals and the secondary crystals were combined and dried under reduced pressure to obtain (4-benzylpiperazin-1-yl) carbamic acid tert-butyl ester (42.22 g, yield 77%) as white powder crystals.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.45 (9 H, s), 2.55 to 2.58 (4 H, m), 2. 80 (4 H, br), 3.51 (2 H, s), 5. 35 (1 H, br), 7 24-7.31 (5 H, m).

Reference Example 36
Preparation of piperazin-1-ylcarbamic acid tert-butyl ester Dissolving (4-benzylpiperazin-1-yl) carbamic acid tert-butyl ester (42.22 g, 145 mmol) prepared in Reference Example 35 in ethanol (300 ml) did. 20% Palladium hydroxide / carbon (6.0 g) was added, stirred at room temperature under hydrogen atmosphere for 20 minutes, and further stirred at 50 ° C. for 30 minutes. After 20% palladium hydroxide / carbon was filtered off through celite, the filtrate was concentrated under reduced pressure. The resulting solid was washed with IPE and filtered. The obtained solid was dried under reduced pressure to obtain piperazin-1-ylcarbamic acid tert-butyl ester (28.9 g, yield 99%) of white powdery crystals.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.46 (9 H, s), 2.74-2.77 (4 H, m), 2.95- 2.99 (4 H, m), 5. 45 (1 H, br).

Reference Example 37
Preparation of 4- (4-trifluoromethylphenoxy) piperidine-1-carboxylic acid tert-butyl ester 4-hydroxypiperidine-1-carboxylic acid tert-butyl ester (2.22 g, 10.0 mmol), 4-hydroxybenzo Trifluoride (1.21 g, 7.45 mmol), tri-n-butylphosphine (2.26 g, 11.2 mmol) and 1,1 '-(azodicarbonyl) dipiperidine (2.82 g, 11.2 mmol) Was dissolved in benzene (20 ml) and stirred at room temperature for 2 days. Water was added to the reaction solution, and extracted with ethyl acetate. After drying over magnesium sulfate and filtration, the obtained filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane / ethyl acetate = 5/1). The colorless oil 4- (4-trifluoromethylphenoxy) piperidine-1-carboxylic acid tert-butyl ester (1.13 g, yield 44%) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.48 (9 H, s), 1.65 to 1.82 (2 H, m), 1.87 to 1.97 (2 H, m), 3.33 to 3.44 (2 H, m), 63-3.74 (2H, m), 4.47-4.58 (1 H, m), 6.89-6.97 (2 H, m), 7.47-7.55 (2 H, m).

Reference Example 38
Preparation of 4- (4-trifluoromethylphenoxy) piperidine 4- (4-trifluoromethylphenoxy) piperidine-1-carboxylic acid tert-butyl ester (1.13 g, 3.27 mmol) prepared in Reference Example 37 It was dissolved in methylene chloride (10 ml). Under room temperature, trifluoroacetic acid (10 ml) was added dropwise and stirred for 5 hours. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in methylene chloride again. The methylene chloride solution was made alkaline with aqueous sodium hydroxide solution and extracted with methylene chloride. The organic phase was washed with brine, dried over magnesium sulfate and filtered. The obtained filtrate was concentrated under reduced pressure to give 4- (4-trifluoromethylphenoxy) piperidine (727 mg, yield 91%) as a white powder.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.63-1.75 (2H, m), 1.97-2.06 (2H, m), 2.69-2.80 (2H, m), 3.10-3.20 (2H, m) 4.38-4.49 (1 H, m), 6.94-6.98 (2 H, m), 7. 50-7. 55 (2 H, m).

  The compounds of Reference Example 39 to Reference Example 43 were produced in the same manner as in Reference Example 38 using the corresponding starting materials.

Reference Example 39
4- (4-Fluorophenoxy) piperidine white powder, 76% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
1.61-1.74 (2H, m), 1.96-2.06 (2H, m), 2.50 (1 H, bs), 2.70-2.80 (2H, m), 11-3.20 (2H, m), 4.23-4. 33 (1H, m), 6.80-6.89 (2H, m), 6.91-7.00 (2H, m).

Reference Example 40
4- (3-Trifluoromethylphenoxy) piperidine white powder, yield 48%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.62-1.76 (2H, m), 1.80 (1H, bs), 1.97-2.08 (2H, m), 2.71-2.81 (2H, m), 3. 11-3.20 (2H, m), 4.37-4.47 (1H, m), 7.05-7.20 (3H, m), 7.34-7.41 (1H, m).

Reference Example 41
4- (4-Trifluoromethoxyphenoxy) piperidine white powder, yield 88%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.59-1.73 (3H, m), 1.97-2.04 (2H, m), 2.68-2.78 (2H, m), 3.10-3. 19 (2H, m) 4.29-4.36 (1 H, m), 6.85-6.92 (2 H, m), 7. 10-7. 14 (2 H, m).

Reference Example 42
4- (4-Cyanophenoxy) piperidine white powder, yield 83%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.63-1.77 (3H, m), 1.98-2.08 (2H, m), 2.72-2.82 (2H, m), 3.12-3. 21 (2H, m) ), 4.42-4.51 (1 H, m), 6.92-6.98 (2 H, m), 7.55-7.61 (2 H, m).

Reference Example 43
4- (4-Chlorophenoxy) piperidine white powder, yield 62%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.50 (1 H, bs), 1.56 to 1.71 (2 H, m), 1.94 to 2.04 (2 H, m), 2.66 to 2.76 (2 H, m), 3. 08-3.18 (2H, m), 4.25-4.35 (1H, m), 6.80-6.86 (2H, m), 7.18-7. 25 (2H, m).

Reference Example 44
Preparation of 1-ethyl-5- (3-methyl-3-butenyl) -1H-tetrazole 1-ethyl-5-methyl-1H-tetrazole (0.80 g, 7.13 mmol) in THF (15 ml)- The mixture was cooled to 70 ° C. and stirred under stirring, n-butyllithium (1.53 M) hexane solution (6.5 ml, 9.98 mmol) was added dropwise and stirred for 1.5 hours, and at the same temperature, 3-chloro-2-methyl- A solution of 1-propene (0.77 ml, 7.84 mmol) in THF (5 ml) was added, and the mixture was further stirred at the same temperature for 2 hours. To the reaction mixture was added water, extracted with ethyl acetate, dried over magnesium sulfate and concentrated under reduced pressure. A brown liquid 1-ethyl-5- (3-methyl-3-butenyl) -1H-tetrazole (0.95 g, 80% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.56 (3 H, t, J = 7.3 Hz), 1. 80 (3 H, s), 2.44-2.67 (2 H, m), 2. 90-3.06 (2 H, m), 4.32 (2H, q, J = 7.3 Hz), 4.65-4.77 (1 H, m), 4.77-4.87 (1 H, m).

  The compounds of Reference Examples 45 and 46 were produced in the same manner as in Reference Example 44 using the corresponding starting materials.

Reference Example 45
1-phenyl-5- (3-methyl-3-butenyl) -1H-tetrazole white powder, 45% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
1.67 (3H, s), 2.49 (2H, t, J = 8.1 Hz), 3.04 (2H, t, J = 8.1 Hz), 4.58-4.65 (1 H, m) ), 4.71-4.77 (1 H, m), 7.43-7.47 (2 H, m), 7.59-7.62 (3 H, m).

Reference Example 46
1- (4-Chlorophenyl) -5- (3-methyl-3-butenyl) -1H-tetrazole white powder, yield 55%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.68 (3 H, s), 2.50 (2 H, t, J = 8.1 Hz), 3.03 (2 H, t, J = 8.1 Hz), 4.58-4.63 (1 H, m) ], 4.71-4.77 (1 H, m), 7. 38-7. 44 (2 H, m), 7.56-7.62 (2 H, m).

Reference Example 47
Preparation of 3- (4-Methyl-4-pentenyl) -3H-benzoxazol-2-one To a mixture of methyltriphenylphosphonium bromide (11 g, 30.8 mmol) and THF (100 ml) under ice-cooling tert -Potassium butoxy (3.5 g, 31.2 mmol) was gradually added and stirred at the same temperature for 20 minutes. Under the same temperature, a solution of 3- (4-oxopentyl) -3H-benzoxazol-2-one (5.6 g, 25.6 mmol) in THF (10 ml) was slowly added dropwise. The mixture was stirred at room temperature for 2 hours. The reaction solution was poured into ice water and extracted twice with ethyl acetate. The organic phases were combined, washed successively with water and saturated brine, and dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (n-hexane / ethyl acetate = 3/1) to give colorless oil 3- (4-methyl-4-pentenyl) -3H-benzoxazol-2-one (3.4 g, A yield of 61% was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.73 (3H, s), 1.84-2.16 (4H, m), 3.83 (2H, t, J = 7.3 Hz), 4.75 (2 H, d, J = 12.7 Hz) 6.97 (1 H, d, J = 8.2 Hz), 7.02-7.28 (3 H, m).

Reference Example 48
Preparation of 3- (5-Methyl-5-hexenyl) -3H-benzoxazol-2-one With 3- (5-oxohexyl) -3H-benzoxazol-2-one (1.4 g, 6 mmol), A colorless oil of 3- (5-methyl-5-hexenyl) -3H-benzoxazol-2-one (1.1 g, yield 79%) was obtained in the same manner as in Reference Example 47.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.42-1.60 (2H, m), 1.65 to 1.83 (5H, m), 2.00-2.16 (2H, m), 3.84 (2H, t, J = 6 .9 Hz), 4.69 (2 H, d, J = 11.7 Hz), 6.97 (1 H, d, J = 7.9 Hz), 7.02-7.23 (3 H, m).

Reference Example 49
Preparation of 5- (4-Trifluoromethoxyphenyl) -3H- [1,3,4] oxadiazol-2-one 4-Trifluoromethoxybenzoic acid hydrazide (5.06 g, 22.98 mmol) in THF Triethylamine (3.52 ml, 25.28 mmol) and 1,1'-carbonyldiimidazole (4.84 g, 29.87 mmol) were added to the solution with ice cooling and stirring under stirring for 2 hours at room temperature. The mixture was concentrated under reduced pressure, water was added, extraction was performed with ethyl acetate, the extract was dried over magnesium sulfate and concentrated under reduced pressure. White solid 5- (4-trifluoromethoxyphenyl) -3H- [1,3,4] oxadiazol-2-one (5.34 g, yield 94%) was obtained.
¹ H-NMR (DMSO-d ₆ ) δ ppm:
7.01 (1 H, s), 7.47-7.59 (2 H, m), 7.86-7.98 (2 H, m).

  The compounds of Reference Example 50 to Reference Example 61 were produced in the same manner as in Reference Example 49 using the corresponding starting materials.

Reference Example 50
5- (4-Trifluoromethylphenyl) -3H- [1,3,4] oxadiazol-2-one white powder, yield 97%
¹ H-NMR (DMSO-d ₆ ) δ ppm:
7.90 (2H, d, J = 8.5 Hz), 7.99 (2H, d, J = 8.5 Hz).

Reference Example 51
5- (4-Biphenylyl) -3H- [1,3,4] oxadiazol-2-one white powder, yield 97%
¹ H-NMR (DMSO-d ₆ ) δ ppm:
7.35-7.52 (3 H, m), 7.68-7. 73 (2 H, m), 7.76-7. 87 (4 H, m).

Reference Example 52
5-phenyl-3H- [1,3,4] oxadiazol-2-one white powder, yield 92%
¹ H-NMR (CDCl ₃ ) δ ppm:
7.40-7.58 (3 H, m), 7.77-7.91 (2 H, m).

Reference Example 53
5- (4-Chlorophenyl) -3H- [1,3,4] oxadiazol-2-one white powder, yield 80%
¹ H-NMR (DMSO-d ₆ ) δ ppm:
7.61 (2H, dd, J = 1.9 Hz, 6.6 Hz), 7.80 (2 H, dd, J = 1.9 Hz, 6.6 Hz).

Reference Example 54
5- (4-Fluorophenyl) -3H- [1,3,4] oxadiazol-2-one white powder, yield 74%
¹ H-NMR (DMSO-d ₆ ) δ ppm:
7.30-7.49 (2H, m), 7.78-7.92 (2H, m).

Reference Example 55
5- (4-Bromophenyl) -3H- [1,3,4] oxadiazol-2-one white powder, yield 87%
¹ H-NMR (DMSO-d ₆ ) δ ppm:
7.65-7.78 (4H, m).

Reference Example 56
5- (4-Chlorobenzyl) -3H- [1,3,4] oxadiazol-2-one white powder, yield 83%
¹ H-NMR (DMSO-d ₆ ) δ ppm:
3.94 (2H, s), 7.31 (2H, dd, J = 2.1 Hz, 6.4 Hz), 7.41 (2 H, dd, J = 2.1 Hz, 6.4 Hz).

Reference Example 57
5- [2- (4-chlorophenyl) ethyl] -3H- [1,3,4] oxadiazol-2-one white powder, yield 78%
¹ H-NMR (DMSO-d ₆ ) δ ppm:
2.76-3.00 (4H, m), 7.27 (2H, d, J = 8.5 Hz), 7.35 (2H, d, J = 8.5 Hz), 12.03 (1 H, s) ).

Reference Example 58
5- (4-Chlorostyryl) -3H- [1,3,4] oxadiazol-2-one white powder, yield 88%
¹ H-NMR (DMSO-d ₆ ) δ ppm:
6.99 (1 H, d, J = 16.5 Hz), 7.32 (1 H, d, J = 16.5 Hz), 7.47 (2 H, d, J = 8.6 Hz), 7.75 (2 H , D, J = 8.6 Hz), 12.06 (1 H, s).

Reference Example 59
5- (4-Chlorophenoxymethyl) -3H- [1,3,4] oxadiazol-2-one white powder, yield 68%
¹ H-NMR (DMSO-d ₆ ) δ ppm:
5.07 (2H, s), 7.07 (2H, d, J = 6.8 Hz), 7.37 (2 H, d, J = 6.8 Hz), 12.41 (1 H, br).

Reference Example 60
5- (4-Pyridyl) -3H- [1,3,4] oxadiazol-2-one white powder, yield 40%
¹ H-NMR (DMSO-d ₆ ) δ ppm:
7.72 (2H, dd, J = 1.6 Hz, 4.6 Hz), 8.76 (2 H, dd, J = 1.6 Hz, 4.6 Hz), 12.90 (1 H, s).

Reference Example 61
5- (2-Pyrimidyl) -3H- [1,3,4] oxadiazol-2-one white powder, yield 70%
¹ H-NMR (DMSO-d ₆ ) δ ppm:
8.68-8.86 (2H, m), 9.12 (1 H, d, J = 1.4 Hz), 12.97 (1 H, s).

Reference Example 62
Preparation of (S) -2- (4-Trifluoromethoxyphenoxymethyl) pyrrolidine-1-carboxylic acid tert-butyl ester 4- (trifluoromethoxy) phenol (2.1 g, 11.8 mmol), (S)- 2-hydroxymethyl pyrrolidine-1-carboxylic acid tert-butyl ester (2 g, 9.8 mmol), diethyl azodicarboxylate (2.3 ml, 14.7 mmol), triphenylphosphine (3.86 g, 14.7 mmol) ) And THF (30 ml) was heated to reflux for 1 h. The reaction solution was returned to room temperature and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (n-hexane / ethyl acetate = 10/1) to give tert-butyl (S) -2- (4-trifluoromethoxyphenoxymethyl) pyrrolidine-1-carboxylate as a slightly yellow oil The ester (2.96 g, 65% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.48 (9 H, s), 1.78-2.10 (4 H, m), 3.27-3. 49 (2 H, m), 3.73-3.98 (1 H, m), 4. 04-4.20 (2H, m), 6.90 (2H, dd, J = 2.2 Hz, 7.0 Hz), 7.12 (2 H, dd, J = 2.2 Hz, 7.0 Hz).

Reference Example 63
Preparation of (S) -2- (4-trifluoromethoxyphenoxymethyl) pyrrolidine (S) -2- (4-trifluoromethoxyphenoxymethyl) pyrrolidine-1-carboxylic acid tert-butyl ester prepared in Reference Example 62 A mixture of 2.31 g, 6.39 mmol), trifluoroacetic acid (20 ml) and methylene chloride (20 ml) was stirred at room temperature for 4 hours. The reaction solution was concentrated under reduced pressure. The residue was basified by adding 10% caustic soda, extracted with methylene chloride and dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure to obtain (S) -2- (4-trifluoromethoxyphenoxymethyl) pyrrolidine (1.65 g, yield 99%) as a pale tea oil.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.41 to 1.63 (1 H, m), 1.65 to 2.04 (3 H, m), 2.70 (1 H, bs), 2.88 to 3.08 (2 H, m), 3. 43-3.59 (1 H, m), 3.78-3.96 (2 H, m), 6.88 (2 H, dd, J = 2.3 Hz, 8.4 Hz), 7.11 (2 H, dd) , J = 2.3 Hz, 8.4 Hz).

Reference Example 64
Preparation of 3-oxo-4- (4-trifluoromethylbenzyl) piperazine-1-carboxylic acid tert-butyl ester 3-oxopiperazine-1-carboxylic acid tert-butyl ester (4.1 g, 20.4 mmol) and To a mixture of DMF (30 ml), sodium hydride (840 mg, 24.5 mmol) was gradually added under ice-cooling, and the mixture was stirred at room temperature for 30 minutes. A solution of 4-trifluoromethylbenzyl chloride (5 g, 20.9 mmol) in DMF (5 ml) was added dropwise under ice-cooling and stirred at room temperature for 2 hours. The reaction solution was poured into ice water and extracted twice with ethyl acetate. The organic phases were combined, washed twice with water, then washed with saturated brine and dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride) to give 3-oxo-4- (4-trifluoromethylbenzyl) piperazine-1-carboxylic acid tert-butyl ester (6.7 g, yield 91) as white powder crystals. %) Got.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.47 (9 H, s), 3.27 (2 H, t, J = 5.7 Hz), 3.62 (2 H, t, J = 5.7 Hz), 4.18 (2 H, s), 4. 67 (2H, s), 7.39 (2H, d, J = 8.1 Hz), 7.61 (2 H, d, J = 8.1 Hz).

Reference Example 65
Preparation of 1- (4-trifluoromethylbenzyl) piperazin-2-one 3-oxo-4- (4-trifluoromethylbenzyl) piperazine-1-carboxylic acid tert-butyl ester (6. 6) prepared in Reference Example 64. In the same manner as in Reference Example 63, 7 g (18.7 mmol) of 1- (4-trifluoromethylbenzyl) piperazin-2-one (4.5 g, yield 93%) was obtained in the same manner as in Reference Example 63. .
¹ H-NMR (CDCl ₃ ) δ ppm:
3.06 (2 H, t, J = 5.2 Hz), 3. 24 (2 H, t, J = 5.2 Hz), 3.62 (2 H, s), 4. 60 (2 H, s), 7. 39 (2H, d, J = 8.1 Hz), 7.59 (2H, d, J = 8.1 Hz).

Reference Example 66
Preparation of 4'-trifluoromethoxybiphenyl-4-carbaldehyde 1-bromo-4- (trifluoromethoxy) benzene (1.53 g, 6.35 mmol), 4-formylbenzeneboronic acid (1 g, 6.67 mmol) A mixture of tetrakis (triphenylphosphine) palladium (147 mg, 0.13 mmol), potassium phosphate (2.02 g, 9.53 mmol) and DMF (10 ml) was stirred at 100 ° C. for 5 hours. The reaction solution is cooled to room temperature, extracted with ethyl acetate, washed three times with water, then washed with saturated brine, and dried over magnesium sulfate. After filtration, the filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (n-hexane / methylene chloride = 3/1) to give 4′-trifluoromethoxybiphenyl-4-carbaldehyde (white powder) 1.56 g (yield 92%) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
7.33 (2H, d, J = 8.8 Hz), 7.60-7.80 (4 H, m), 7.97 (2 H, d, J = 8.2 Hz), 10.07 (1 H, s ).

  The compounds of Reference Examples 67 to 73 were produced from the corresponding iodobenzene or brominated benzene compound and formylbenzeneboronic acid in the same manner as in Reference Example 66.

Reference Example 67
4'-Trifluoromethylbiphenyl-4-carbaldehyde colorless powder crystals, yield 27%
¹ H-NMR (CDCl ₃ ) δ ppm:
7.68-7.81 (6 H, m), 7.99 (2 H, dd, J = 1.7 Hz, 6.5 Hz), 10.09 (1 H, s).

Reference Example 68
4'-Trifluoromethylbiphenyl-3-carbaldehyde yellow oil, yield 83%
¹ H-NMR (CDCl ₃ ) δ ppm:
7.33 (2H, d, J = 8.8 Hz), 7.60-7.80 (4 H, m), 7.97 (2 H, d, J = 8.2 Hz), 10.07 (1 H, s ).

Reference Example 69
4'-Dimethylaminobiphenyl-4-carbaldehyde yellow powder, yield 46%
¹ H-NMR (CDCl ₃ ) δ ppm:
3.03 (6 H, s), 6.81 (2 H, dd, J = 2.1 Hz, 6.8 Hz), 7.58 (2 H, dd, J = 2.1 Hz, 6.8 Hz), 7.71 (2H, dd, J = 1.8 Hz, 6.6 Hz), 7.90 (2 H, dd, J = 1.8 Hz, 6.6 Hz), 10.00 (1 H, s).

Reference Example 70
4'-Chlorobiphenyl-4-carbaldehyde slightly yellow powder crystal, 47% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
7.45 (2H, d, J = 8.6 Hz), 7.57 (2 H, d, J = 8.6 Hz), 7.73 (2 H, d, J = 8.4 Hz), 7.96 (2 H) , D, J = 8.4 Hz), 10.06 (1 H, s).

Reference Example 71
2'-Chlorobiphenyl-4-carbaldehyde white powder crystal, 46% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
7.30-7.40 (3H, m), 7.38-7.58 (1H, m), 7.63 (2H, d, J = 8.1 Hz), 7.96 (2H, d, J = 8.1 Hz), 10.08 (1 H, s).

Reference Example 72
3 ', 4'-Dichlorobiphenyl-4-carbaldehyde white powder crystal, 24% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
7.46 (1H, dd, J = 2.1 Hz, 8.4 Hz), 7.56 (1 H, d, J = 8.4 Hz), 7.70-7.80 (3 H, m), 7.97 (2H, dd, J = 1.8 Hz, 6.6 Hz), 10.07 (1 H, s).

Reference Example 73
4'-Methoxybiphenyl-4-carbaldehyde white powder crystal, 45% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
3.87 (3 H, s), 7.01 (2 H, d, J = 6.8 Hz), 7.59 (2 H, d, J = 6.8 Hz), 7.72 (2 H, d, J = 8 .3 Hz), 7.93 (2 H, d, J = 8.3 Hz), 10.04 (1 H, s).

Reference Example 74
Preparation of 4- (Pyridin-3-yl) benzaldehyde 4-bromobenzaldehyde (2 g, 10.8 mmol), diethyl (3-pyridyl) borane (1.75 g, 11.9 mmol), tetrakis (triphenylphosphine) palladium A mixture of (375 mg, 0.32 mmol), 2N sodium carbonate (10.8 ml, 21.6 mmol) and toluene (40 ml) was heated to reflux overnight under a nitrogen atmosphere. The reaction was brought to room temperature and diluted with ethyl acetate. After washing with water, it was washed with saturated brine and dried over sodium sulfate. After filtration, the filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (n-hexane / ethyl acetate = 1/1) to give 4- (pyridin-3-yl) benzaldehyde (a slight yellow powder crystal) 1.43 g (yield 72%) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
7.33-7.50 (1 H, m), 7.76 (2 H, dd, J = 1.8 Hz, 6.6 Hz), 7.89-8.06 (3 H, m), 8.56-8 .69 (1 H, m), 8. 90 (1 H, dd, J = 0.7 Hz, 1.7 Hz), 10.09 (1 H, s).

Reference Example 75
Preparation of 4- (Imidazol-1-yl) benzaldehyde 4-Fluorobenzaldehyde (4.96 g, 40 mmol), imidazole (2.86 g, 42 mmol), potassium carbonate (6.08 g, 44 mmol) and DMSO (40 ml) The mixture was stirred at 110.degree. C. overnight. The reaction solution was returned to room temperature, poured into ice water (100 ml), and the precipitated crystals were collected by filtration. After washing with water, the residue was washed with ethyl acetate to obtain 4- (imidazol-1-yl) benzaldehyde (2.33 g, yield 34%) as pale yellow powdery crystals.
¹ H-NMR (CDCl ₃ ) δ ppm:
7.20-7.30 (1H, m), 7.38 (1H, dd, J = 1.3 Hz, 1.4 Hz), 7.58 (2 H, dd, J = 1.8 Hz, 6.8 Hz) , 7.98-8.10 (3 H, m), 1 0.05 (1 H, s).

  The compound of Reference Example 76 was produced in the same manner as in Reference Example 75 using the corresponding starting materials.

Reference Example 76
4- (Piperidin-1-yl) benzaldehyde yellow powder crystal, 46% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
1.58-1.75 (6H, m), 3.33-3.50 (4H, m), 6.89 (2H, dd, J = 1.9 Hz, 7.0 Hz), 7.73 (2 H) , Dd, J = 1.9 Hz, 7.0 Hz), 9.75 (1 H, s).

Reference Example 77
Preparation of 4- (4-trifluoromethylphenyl) piperazine-1-carboxylic acid tert-butyl ester 4-bromobenzotrifluoride (3.0 g, 13.3 mmol), piperazine-1-carboxylic acid tert-butyl ester 2.9 g (15.3 mmol), bis (dibenzylideneacetone) palladium (306 mg, 0.53 mmol), tri-o-tolylphosphine (162 mg, 0.53 mmol) and sodium tert-butoxy (2.2 g, 22.7 mmol) was heated to reflux for 4 hours in toluene (60 ml) under a nitrogen atmosphere. Ethyl acetate and water were added to the reaction solution and the mixture was stirred, and the precipitate was removed by celite filtration, and the filtrate was extracted with ethyl acetate. The organic phase was washed with brine, dried over magnesium sulfate and filtered. The obtained filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (n-hexane / methylene chloride = 2/1) to give 4- (4-trifluoromethylphenyl) piperazine-1-carboxylic acid as white powder. The tert-butyl ester (3.8 g, yield 87%) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.49 (9H, s), 3.21-3.26 (4H, m), 3.56-3.61 (4H, m), 6.90-6. 93 (2H, m), 7.. 47-7.51 (2H, m).

  The compounds of Reference Examples 78 to 84 were produced in the same manner as in Reference Example 77 using the corresponding starting materials.

Reference Example 78
4- (4-Trifluoromethoxyphenyl) piperazine-1-carboxylic acid tert-butyl ester white powder, yield 95%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.48 (9 H, s), 3.09-3.13 (4 H, m), 3.55-3. 60 (4 H, m), 6.87-6.91 (2 H, m), 7.. 10-7.14 (2H, m).

Reference Example 79
4- (4-Biphenylyl) piperazine-1-carboxylic acid tert-butyl ester white powder, 95% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
1.49 (9 H, s), 3.16 to 3.21 (4 H, m), 3.58 to 3.62 (4 H, m), 6.97 to 7.01 (2 H, m), 7. 27-7. 32 (1 H, m), 7. 37-7. 44 (2 H, m), 7. 50-7. 58 (4 H, m).

Reference Example 80
4- (4-Dimethylaminophenyl) piperazine-1-carboxylic acid tert-butyl ester white powder, yield 79%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.48 (9H, s), 2.87 (6H, s), 2.96-3.00 (4H, m), 3.54-3.59, (4H, m), 6.72-6 77 (2H, m), 6.87-6.92 (2H, m).

Reference Example 81
4- (3-Pyridyl) piperazine-1-carboxylic acid tert-butyl ester white powder, yield 99%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.49 (9H, s), 3.14-3.19 (4H, m), 3.57-3.62 (4H, m), 7.17-7.19 (2H, m), 8. 12-8.14 (1 H, m), 8.31-8. 33 (1 H, m).

Reference Example 82
4- (4-Ethoxycarbonylphenyl) piperazine-1-carboxylic acid tert-butyl ester white powder, 42% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
1.37 (3 H, t, J = 7.1 Hz), 1.48 (9 H, s), 3. 27-3. 22 (4 H, m), 3.5 6-3. 60 (4 H, m), 4.33 (2H, q, J = 7.1 Hz), 6.84-6.88 (2H, m), 7.92-7.96 (2H, m).

Reference Example 83
4- (4-Methylphenyl) piperazine-1-carboxylic acid tert-butyl ester white powder, yield 55%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.48 (9 H, s), 2.27 (3 H, s), 3.04-3.09 (4 H, m), 3.55-3.59 (4 H, m), 6.82-6. 87 (2H, m), 7.06-7. 10 (2H, m).

Reference Example 84
4- (4-Cyanophenyl) piperazine-1-carboxylic acid tert-butyl ester white powder, 86% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
1.49 (9 H, s), 3. 28-3. 33 (4 H, m), 3.5 6-3. 60 (4 H, m), 6.8 3-6. 87 (2 H, m), 7. 49-7.53 (2H, m).

Reference Example 85
Preparation of 1- (4-trifluoromethylphenyl) piperazine 4- (4-trifluoromethylphenyl) piperazine-1-carboxylic acid tert-butyl ester (3.8 g, 11.5 mmol) prepared in Reference Example 77 was used. It was dissolved in methylene chloride (40 ml), trifluoroacetic acid (10 ml) was added dropwise and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure, and the residue was neutralized with saturated aqueous sodium hydrogen carbonate solution and extracted with methylene chloride. The organic phase was dried over magnesium sulfate and filtered. The obtained filtrate was concentrated under reduced pressure to obtain 1- (4-trifluoromethylphenyl) piperazine (2.5 g, yield 96%) as a white powder.
¹ H-NMR (CDCl ₃ ) δ ppm:
3.01-3.06 (4H, m), 3.21-3.26 (4H, m), 6.92 (2H, d, J = 8.6 Hz), 7.48 (2H, d, J = 8.6 Hz).

  The compounds of Reference Example 86 to Reference Example 89 were produced in the same manner as in Reference Example 85 using the corresponding starting materials.

Reference Example 86
1- (4-Trifluoromethoxyphenyl) piperazine white powder, 100% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
1.61 (1 H, s), 3.00-3.05 (4 H, m), 3.10-3.15 (4 H, m), 6.85-6. 92 (2 H, m), 7.. 08-7. 13 (2H, m).

Reference Example 87
1- (4-Dimethylaminophenyl) piperazine white powder, yield 99%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.60 (1H, br), 2.86 (6H, s), 3.01 (8H, br), 6.71 to 6.78 (2H, m), 6.87 to 6.92 (2H, s) m).

Reference Example 88
1- (3-Pyridyl) piperazine white powder, 100% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
2.09 (1 H, s), 3.03-3.09 (4 H, m), 3.14-3.20 (4 H, m), 7.16-7.18 (2 H, m), 8. 09-8.11 (1 H, m), 8.31 (1 H, s).

Reference Example 89
1- (4-Ethoxycarbonylphenyl) piperazine white powder, 95% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
1.37 (3 H, t, J = 7.1 Hz), 1.84 (1 H, s), 3.00 to 3.04 (4 H, m), 3.26 to 3.31 (4 H, m), 4.33 (2H, q, J = 7.1 Hz), 6.83-6.89 (2H, m), 7.89-7.96 (2H, m).

Reference Example 90
Preparation of 4- (piperazin-1-yl) benzoic acid tert-butyl ester 4-bromobenzoic acid tert-butyl ester (4.8 g, 18.8 mmol), piperazine (9.7 g, 0.11 mol), acetic acid Palladium (85 mg, 0.38 mmol), (S)-(-)-BINAP (352 mg, 0.57 mmol) and tert-butoxy sodium (2.7 g, 28.2 mmol) in toluene (50 ml), nitrogen The mixture was heated to reflux under an atmosphere for 2 hours. Ethyl acetate and water were added to the reaction solution and the mixture was stirred, and the precipitate was removed by celite filtration, and the filtrate was extracted with ethyl acetate. The organic phase was washed with brine, dried over magnesium sulfate and filtered. The obtained filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (methylene chloride / methanol = 5/1) to obtain gray powder of 4- (piperazin-1-yl) benzoic acid tert-butyl ester (3. 3). 8 g (yield 77%) were obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.57 (9 H, s), 3.00-3.04 (4 H, m), 3.24-3.29 (4 H, m), 6.83-6.87 (2 H, m), 7. 85-7.89 (2H, m).

Reference Example 91
Preparation of piperazine-1-carboxylic acid 4-trifluoromethoxybenzyl ester 4-trifluoromethoxybenzyl alcohol (25 g, 130.11 mmol) and phenyl chloroformate (20.37 g, 130.11 mmol) in ethyl acetate (125 ml) And cooled to 3 ° C. A solution of pyridine (11.6 ml, 143.12 mmol) in ethyl acetate (50 ml) was added dropwise over 15 minutes at 15 ° C. or less. It stirred for 30 minutes under the same temperature. The reaction mixture was washed successively with water, 3N hydrochloric acid, 10% aqueous potassium carbonate solution and saturated brine and dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to give carbonate as a colorless oil. Piperazine (33.62 g, 390.34 mmol) was dissolved in methanol (125 ml) and cooled to 3 ° C. A solution in which the above carbonate was dissolved in ethyl acetate (50 ml) was added dropwise thereto at 10 ° C. or less over 25 minutes. It stirred under the same temperature for 1 hour. The reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride / methanol = 10/1). A colorless oil of piperazine-1-carboxylic acid 4-trifluoromethoxybenzyl ester (35.33 g, 89% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
2.57-2.96 (4H, m), 3.42-3.63 (4H, m), 5.13 (2H, s), 7.21 (2H, d, J = 8.5 Hz), 7.39 (2H, d, J = 8.5 Hz).

Reference Example 92
Preparation of piperazine-1-carboxylic acid 3- (4-trifluoromethylphenyl) -2-propenyl ester 3- (4-trifluoromethylphenyl) -2-propen-1-ol (1 g, 4.95 mmol), A solution of pyridine (0.5 ml, 6.18 mmol) in ethyl acetate (2 ml) in a mixture of phenyl chloroformate (0.72 ml, 5.69 mmol) and ethyl acetate (5 ml) under ice-cooling It dripped gradually. The mixture was stirred at room temperature for 1 hour. The reaction mixture was washed successively with water, 3N hydrochloric acid, 10% aqueous potassium carbonate solution and saturated brine and dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to give carbonate as a colorless oil. Piperazine (1.28 g, 14.84 mmol) was dissolved in methanol (5 ml), and a solution of the above carbonate dissolved in ethyl acetate (5 ml) was gradually added dropwise under ice-cooling. The mixture was stirred at room temperature for 2.5 hours. The reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride / methanol = 10/1). There was obtained piperazine-1-carboxylic acid 3- (4-trifluoromethylphenyl) -2-propenyl ester (1.4 g, yield 90%) as a colorless oil.
¹ H-NMR (CDCl ₃ ) δ ppm:
2.75-2.95 (4H, m), 3.43-3.57 (4H, m), 4.78 (2H, dd, J = 1.2 Hz, 6.0 Hz), 6.33-6 .43 (1 H, m), 6.66 (1 H, d, 16.0 Hz), 7.48 (2 H, d, J = 8.4 Hz), 7.57 (2 H, d, J = 8.4 Hz) .

  The compound of Reference Example 93 was produced in the same manner as in Reference Example 92 using the corresponding starting materials.

Reference Example 93
Piperazine-1-carboxylic acid 3- (4-trifluoromethoxyphenyl) -2-propenyl ester colorless oil, yield 90%
¹ H-NMR (CDCl ₃ ) δ ppm:
2.75-2.88 (4H, m), 3.44-3.52 (4H, m), 4.75 (2H, dd, J = 1.3 Hz, 6.2 Hz), 6.29 (1 H) , Dt, J = 6.2 Hz, 15.9 Hz), 6.62 (1 H, d, J = 15.9 Hz), 7.15 to 7.18 (2 H, m), 7.38 to 7.42 2H, m).

Reference Example 94
Preparation of 4- (4-Chlorophenyl) -1,2,3,6-tetrahydropyridine-1-carbonyl chloride 4- (4-Chlorophenyl) -1,2,3,6-tetrahydropyridine hydrochloride (1 g, 4. A mixture of 3 mmol), pyridine (680 mg, 8.6 mmol), triphosgene (430 mg, 1.45 mmol) and toluene (20 ml) was heated to reflux for 3 hours. The reaction was brought to room temperature and diluted with diethyl ether. It wash | cleaned in order of 10% hydrochloric acid, water, and a saturated salt solution, and dried with magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure to obtain 4- (4-chlorophenyl) -1,2,3,6-tetrahydropyridine-1-carbonyl chloride (1 g, yield 90%) as a yellow oil.
¹ H-NMR (CDCl ₃ ) δ ppm:
2.51-2.72 (2H, m), 3.81-4.00 (2H, m), 4.26-4.40 (2H, m), 5.93-6.09 (1 H, m) ), 7.16-7.35 (4H, m).

Reference Example 95
Preparation of 1-benzyl-4- (4-trifluoromethylphenyl) piperidin-4-ol 4-Bromobenzotrifluoride (1 g, 4.44 mmol) was dissolved in THF (15 ml) and n -70 ° C. -A butyl lithium (1.5 M) hexane solution (3.1 ml, 4.67 mmol) was added dropwise. Under the same temperature, a solution of 1-benzyl-4-piperidone dissolved in THF (15 ml) was added dropwise, and the mixture was stirred for 2 hours and then at room temperature for 2 hours. The reaction solution was diluted with ethyl acetate, washed successively with water and saturated brine, and dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane / acetone = 2/1) to give 1-benzyl-4- (4-trifluoromethylphenyl) piperidin-4-ol (692 mg, yield 46) as white powder crystals. %) Got.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.60-1.78 (2H, m), 2.07-2. 25 (2H, m), 2.38-2.54 (2H, m), 2.74-2.87 (2H, m) ), 3.59 (2H, s), 7.20-7.38 (5H, m), 7.51-7.67 (4H, m).

Reference Example 96
Preparation of 1-benzyl-4- (4-trifluoromethylphenyl) -1,2,3,6-tetrahydropyridine 1-benzyl-4- (4-trifluoromethylphenyl) piperidine-4 prepared in Reference Example 95 A mixture of -ol (692 mg, 2.06 mmol), concentrated hydrochloric acid (4.5 ml) and acetic acid (10 ml) was heated to reflux overnight. The reaction was brought to room temperature and diluted with methylene chloride. The extract was washed successively with water, 10% sodium hydroxide and saturated brine and dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (n-hexane / acetone = 4/1) to give 1-benzyl-4- (4-trifluoromethylphenyl) -1,2,3,6-tetrahydro as pale yellow powder crystal. Pyridine (528 mg, 80% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
2.50-2.60 (2H, m), 2.62-2.76 (2H, m), 3.11-3.22 (2H, m), 3.65 (2H, s), 6. 10-6.20 (1 H, m), 7.20-7.54 (9 H, m).

Reference Example 97
Preparation of 4- (4-trifluoromethylphenyl) -1,2,3,6-tetrahydropyridine hydrochloride 1-benzyl-4- (4-trifluoromethylphenyl) -1,2,3 prepared in Reference Example 96 3,6-Tetrahydropyridine (2 g, 6.3 mmol) is dissolved in methylene chloride (20 ml) and 2-chloroethyl chloroformate (1.67 g, 11.68) under nitrogen atmosphere with ice cooling. The solution was added dropwise and stirred at the same temperature for 3 hours. Methanol (20 ml) was added and heated to reflux for 1 hour. The reaction solution is returned to room temperature, diethyl ether is added, and the precipitated crystals are collected by filtration to give 4- (4-trifluoromethylphenyl) -1,2,3,6-tetrahydropyridine hydrochloride (1 of white powder crystals). .44 g (yield 87%) were obtained.
¹ H-NMR (DMSO-d ₆ ) δ ppm:
2.64-2.80 (2H, m), 3.18-3. 34 (2H, m), 3.68-3.80 (2H, m), 6.25-6. 39 (1H, m) ), 7.61-7.80 (4H, m).

Reference Example 98
Preparation of 4- (4-trifluoromethylphenyl) -1,2,3,6-tetrahydropyridine-1-carbonyl chloride 4- (4-trifluoromethylphenyl) -1,2,3 prepared in Reference Example 97 Yellow oil according to Reference Example 94 using 3,6-tetrahydropyridine hydrochloride (300 mg, 1.14 mmol), pyridine (0.18 ml, 2.28 mmol) and triphosgene (112 mg, 0.38 mmol) There was obtained 4- (4-trifluoromethylphenyl) -1,2,3,6-tetrahydropyridine-1-carbonyl chloride (220 mg, yield 67%) of
¹ H-NMR (CDCl ₃ ) δ ppm:
2.57-2.75 (2H, m), 3.82-4.00 (2H, m), 4.25-4. 40 (2H, m), 6.05-6.16 (1 H, m) ), 7.47 (2H, d, J = 8.2 Hz), 7.59 (2 H, d, J = 8.2 Hz).

Reference Example 99
Preparation of 4- (4-chlorophenyl) piperidine hydrochloride 4- (4-chlorophenyl) -1,2,3,6-tetrahydropyridine hydrochloride (2 g, 8.7 mmol) was dissolved in ethanol (100 ml) and oxidized Atmospheric pressure catalytic reduction was carried out at room temperature using platinum (100 mg) as a catalyst. The reaction solution was filtered through celite, and the filtrate was concentrated under reduced pressure. The crystals obtained by treating the residue with diethyl ether were collected by filtration to give 4- (4-chlorophenyl) piperidine hydrochloride (1.9 g, yield 94%) as a pale ash powder.
¹ H-NMR (DMSO-d ₆ ) δ ppm:
1.75-1.95 (4H, m), 2.74-3.05 (3H, m), 3.25-3.44 (2H, m), 7.25 (2H, d, J = 8) .5 Hz), 7.38 (2 H, d, J = 8.5 Hz).

Reference Example 100
Preparation of 4- (4-trifluoromethylphenyl) piperidine 1-benzyl-4- (4-trifluoromethylphenyl) -1,2,3,6-tetrahydropyridine prepared in Reference Example 96 (528 mg, 1.66) C. Methanol was dissolved in acetic acid (5 ml), and atmospheric pressure catalytic reduction was carried out at room temperature using 10% palladium / carbon (50 mg) as a catalyst. The reaction solution was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was dissolved in methylene chloride, washed successively with water, 10% sodium hydroxide and brine, and dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to give 4- (4-trifluoromethylphenyl) piperidine (400 mg, quantitative) as a yellow oil.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.72-2.00 (4H, m), 2.61-2.84 (3H, m), 3.07-3. 27 (2H, m), 7.32 (2H, d, J = 8 .2 Hz), 7.56 (2 H, d, J = 8.2 Hz).

Reference Example 101
Preparation of 4- (4-trifluoromethylphenyl) piperidine-1-carbonyl chloride Using 4- (4-trifluoromethylphenyl) piperidine (760 mg, 3.32 mmol) prepared in Reference Example 100, Similarly, 4- (4-trifluoromethylphenyl) piperidine-1-carbonyl chloride (crude product) of pale tea oil was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.65-1.84 (2H, m), 1.86-2.02 (2H, m), 2.77-3.28 (3H, m), 4.42-4.60 (2H, m) ), 7.32 (2H, d, J = 8.1 Hz), 7.59 (2H, d, J = 8.1 Hz).

Reference Example 102
Preparation of 2- [3- (4-trifluoromethylphenyl) -2-propenyl] phthalimide 4- (trifluoromethyl) cinnamyl alcohol (3 g, 14.84 mmol) was dissolved in THF (60 ml) to give phthalimide ( 2.84 g (19.29 mmol) and triphenylphosphine (5.84 g, 22.26 mmol) were added, and a solution of diethyl azodicarboxylate (3.87 g, 22.26 mmol) in THF (20 ml) was added. It dripped gradually. The mixture was stirred at room temperature for 3 hours. The reaction solution is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (n-hexane / methylene chloride = 1/1) to give 2- [3- (4-trifluoromethylphenyl) -2 as a white powder. -Propenyl] phthalimide (4.57 g, 93% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
4.47 (2H, dd, J = 1.2 Hz, 6.3 Hz), 6.27-6.41 (1 H, m), 6.68 (1 H, d, J = 15.9 Hz), 7.44 (2H, d, J = 8.4 Hz), 7.54 (2 H, d, J = 8.4 Hz), 7.74 (2 H, dd, J = 2.0 Hz, 7.0 Hz), 7.85 ( 2H, dd, J = 2.0 Hz, 7.0 Hz).

Reference Example 103
Preparation of 3- (4-Trifluoromethylphenyl) -2-propenylamine 2- [3- (4-trifluoromethylphenyl) -2-propenyl] phthalimide (4.57 g, 13.79) prepared in Reference Example 102 A mixture of mmol), hydrazine hydrate (897 mg, 17.93 mmol) and ethanol (80 ml) was heated to reflux for 3 hours. The reaction was allowed to warm to room temperature, filtered and the filtrate was concentrated under reduced pressure. Ethyl acetate was added to the residue, and the mixture was washed successively with 1N caustic soda and saturated brine and dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure to give 3- (4-trifluoromethylphenyl) -2-propenylamine (2.78 g, quantitative) as pale tea powder crystals.
¹ H-NMR (CDCl ₃ ) δ ppm:
3.51 (2H, d, J = 4.7 Hz), 6.31-6.47 (1 H, m), 6.55 (1 H, d, J = 16.0 Hz), 7.45 (2 H, d , J = 8.3 Hz), 7.55 (2 H, d, J = 8.3 Hz).

Reference Example 104
Preparation of Piperazin-1-yl- (5-chlorobenzofuran-2-ylmethylene) amine 1-Aminopiperazine (29 g, 287 mmol) is dissolved in isopropyl alcohol (173 ml) and 5-chlorobenzofuran-2-aldehyde (34. 52 g (191 mmol) was added and stirred at room temperature for 16 hours. The reaction solution is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography to obtain piperazin-1-yl- (5-chlorobenzofuran-2-ylmethylene) amine (49.49 g, yield 98%) as yellow powdery crystals. Got).
¹ H-NMR (CDCl ₃ ) δ ppm:
2.95-3.10 (4H, m), 3.17-3.29 (4H, m), 6.70 (1H, s), 7.20 (1 H, dd, J = 2.1 Hz, 8 .7 Hz), 7.38-7.52 (3 H, m).

Reference Example 105
Preparation of Piperazin-1-yl- (4-trifluoromethylbenzylidene) amine Piperazin-1-yl-carbamic acid tert-butyl ester (403 mg, 2.0 mmol) was suspended in methylene chloride (4 ml), trifluoroacetic acid was added (1.6 ml) was added and stirred at room temperature for 5 minutes. To the reaction mixture was added 4- (trifluoromethyl) benzaldehyde (0.3 ml, 2.2 mmol) and stirred at room temperature for 1 hour. The reaction solution is poured into aqueous sodium hydrogen carbonate solution, extracted with ethyl acetate, washed with saturated brine, dried over sodium sulfate and concentrated under reduced pressure, and the residue is concentrated by silica gel column chromatography (methylene chloride / methanol = 9 / The residue was purified by 1) to give piperazin-1-yl- (4-trifluoromethylbenzylidene) amine (432 mg, yield 84%) as a white solid.
¹ H-NMR (CDCl ₃ ) δ ppm:
3.00-3.29 (8 H, m), 7.43-7.62 (3 H, m), 7.68 (2 H, d, J = 8.2 Hz).

Reference Example 106
Preparation of piperazin-1-yl- (4-trifluoromethoxybenzylidene) amine To 4-benzylpiperazin-1-ylamine (43.18 g, 225 mmol) was added ethanol (400 ml) and palladium hydroxide / carbon (6.50 g) A suspension of ethanol (30 ml) was added, and stirred under hydrogen atmosphere at room temperature for 3 hours and at 50 ° C. for 2 hours. The reaction mixture was filtered through celite, 4- (trifluoromethoxy) benzaldehyde (42.92 g, 225 mmol) was added to the filtrate, and the mixture was stirred at room temperature for 1.5 hours. The reaction mixture is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (methylene chloride / methanol = 10/1) to give pale yellow powdery crystals of piperazin-1-yl- (4-trifluoromethoxybenzylidene). An amine (56.88 g, 93% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
3.00-3.23 (8 H, m), 7.18 (2 H, d, J = 8.7 Hz), 7.58 (1 H, s), 7.62 (2 H, d, J = 8.7 Hz ).

  The compound of Reference Example 107 was produced in the same manner as in Reference Example 106 using the corresponding starting materials.

Reference Example 107
Piperazin-1-yl- (5-trifluoromethylbenzofuran-2-ylmethylene) amine slightly yellow powder crystal, yield 77%
¹ H-NMR (CDCl ₃ ) δ ppm:
3.00-3.14 (4H, m), 3.23-3.32 (4H, m), 6.79 (1 H, s), 7.41-7.59 (3 H, m), 7. 82 (1 H, s).

Reference Example 108
Preparation of (4-benzylpiperazin-1-yl)-(4-trifluoromethylphenyl) amine 4-bromobenzotrifluoride (3.00 g, 13.3 mmol), 4-benzylpiperazin-1-ylamine (3. 06 g (16.0 mmol), palladium acetate (60 mg, 0.267 mmol), (S)-(-)-BINAP (174 mg, 0.280 mmol), sodium tert-butoxy (1.92 g, 20.0 mmol) ) Was heated under reflux in toluene (60 ml) for 7 hours under a nitrogen atmosphere. Water was added and extracted with ethyl acetate. The organic phase was washed with brine, dried over sodium sulfate and filtered. The obtained filtrate is dried under reduced pressure, and the residue is purified by silica gel column chromatography (n-hexane / acetone = 4/1) to obtain a slightly yellow liquid (4-benzylpiperazin-1-yl)-(4-trifluoro) Methylphenyl) amine (2.666 g, 59% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
2.58 (4H, br), 2.76 (4H, br), 3.55 (2H, s), 4.65 (1H, br), 6.90 (2H, d, J = 8.6 Hz) , 7.23-7.35 (5H, m), 7.41 (2H, d, J = 8.6 Hz).

Reference Example 109
Preparation of piperazin-1-yl- (4-trifluoromethylphenyl) amine The (4-benzylpiperazin-1-yl)-(4-trifluoromethylphenyl) amine prepared in Reference Example 108 was dissolved in ethanol (50 ml) did. 10% Palladium / carbon (0.53 g) was added and stirred at room temperature under hydrogen atmosphere for 6 hours. The mixture was further stirred at 60 ° C. for 10 hours. The reaction solution was filtered through celite, 10% palladium / carbon (0.53 g) was added to the filtrate, and the mixture was stirred at 60 ° C. for 8 hours under a hydrogen atmosphere. After filtering off 10% palladium / carbon through celite, the filtrate was concentrated under reduced pressure. The obtained solid was dried under reduced pressure to obtain piperazin-1-yl- (4-trifluoromethylphenyl) amine (1.76 g, yield 90%) as a colorless solid.
¹ H-NMR (CDCl ₃ ) δ ppm:
2.71 (4H, br), 3.00 (4H, t, J = 4.8 Hz), 4.71 (1 H, br), 6.92 (2 H, d, J = 8.5 Hz), 7. 42 (2H, d, J = 8.5 Hz).

Reference Example 110
Preparation of 4- (3-phenyl-2-propenyloxy) piperidine-1-carboxylic acid tert-butyl ester 4-hydroxypiperidine-1-carboxylic acid tert-butyl ester (0.396 g, 1,97 mmol) in DMF The product was dissolved in 5 ml), sodium hydride (0.086 g, 2.16 mmol) was added, and the mixture was stirred at room temperature for 1 hour. Under ice cooling, cinnamyl chloride (0.300 g, 1.97 mmol) was added, and the mixture was warmed to room temperature and stirred overnight. After extraction with ethyl acetate, the organic phases were combined and washed with water and brine. After drying over magnesium sulfate, it was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane / ethyl acetate = 6/1) to give 4- (3-phenyl-2-propenyloxy) piperidine-1-carboxylic acid tert-butyl ester (0. 0) as a yellow liquid. 314 g (yield 50%) were obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.46 (9 H, s), 1.48-1.59 (2 H, m), 1.81-1. 93 (2 H, m), 3.01-3. 15 (2 H, m), 3. 50-3.61 (1 H, m), 3.74-3.87 (2 H, m), 4.19 (2 H, d, J = 5.9 Hz), 6.29 (1 H, ddd, J = 5) 9 Hz, 5.9 Hz, 15.9 Hz), 6.61 (1 H, d, J = 15.9 Hz), 7.18 to 7.43 (5 H, m).

Reference Example 111
Preparation of 4- (3-phenyl-2-propenyloxy) piperidine 4- (3-phenyl-2-propenyloxy) piperidine-1-carboxylic acid tert-butyl ester prepared in Reference Example 110 (0.314 g, 0. 1). 989 mmol) was dissolved in ethanol (10 ml), 6N hydrochloric acid (3 ml, 18 mmol) was added, and the mixture was stirred at 60 ° C. for 1 hour. The reaction mixture was made alkaline with aqueous sodium hydroxide solution and then extracted with methylene chloride. The organic phases were combined and washed with brine. The organic phase was dried over sodium sulfate and filtered. The obtained filtrate was concentrated under reduced pressure and dried under reduced pressure to obtain 4- (3-phenyl-2-propenyloxy) piperidine (0.198 g, yield 92%) as a yellow liquid.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.40-1.57 (2H, m), 1.91-2.02 (2H, m), 2.56-2.70 (2H, m), 3.12 (2H, ddd, J = 4 .2 Hz, 4.2 Hz, 12.8 Hz), 3.42-3.52 (1 H, m), 4.19 (2 H, d, J = 5.9 Hz), 6.30 (1 H, ddd, J = 5.9 Hz, 5.9 Hz, 15.9 Hz), 6.57 (1 H, d, J = 15.9 Hz), 7.20-7.43 (5 H, m).

Reference Example 112
Preparation of 4- [3- (4-Chlorophenyl) -2-propenyloxy] piperidine-1-carboxylic acid tert-butyl ester 4-hydroxypiperidine-1-carboxylic acid tert-butyl ester (3.58 g, 17.8 mmol Was dissolved in DMF (30 ml), sodium hydride (0.71 g, 17.8 mmol) was added, and the mixture was stirred at room temperature for 2 hours.

  Meanwhile, 4-chlorocinnamyl alcohol (3.00 g, 17.8 mmol) is dissolved in methylene chloride (60 ml), triethylamine (5 ml, 35.6 mmol) and methanesulfonyl chloride (2.1 ml, 26.7 mmol) ) Was added dropwise with ice-cooling and stirred at room temperature for 1.5 hours. Water was added and the mixture was extracted with methylene chloride, and the organic phases were combined and washed with aqueous hydrochloric acid solution, aqueous sodium bicarbonate solution and saturated brine. The organic phase was dried over magnesium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The residue was dissolved in 10 ml DMF.

To this solution, the previously prepared DMF solution was added under ice-cooling, and the mixture was warmed to room temperature and stirred overnight. After extraction with ethyl acetate, the organic phases were combined and washed with water and brine. The organic phase was dried over sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (n-hexane / ethyl acetate = 6/1) and tert-butyl 4- [3- (4-chlorophenyl) -2-propenyloxy] piperidine-1-carboxylate as yellow liquid The ester (0.759 g, 12% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.46 (9 H, s), 1.50 to 1.62 (2 H, m), 1.83 to 1.94 (2 H, m), 3.03 to 3.14 (2 H, m), 3. 53-3.58 (1H, m), 3.77-3.83 (2H, m), 4.17 (1H, d, J = 5.7 Hz), 4.18 (1 H, d, J = 5 .7 Hz), 6.27 (1 H, ddd, J = 5.7 Hz, 5.7 Hz, 15.9 Hz), 6.57 (1 H, d, J = 15.9 Hz), 7.20-7. 4H, m).

Reference Example 113
Preparation of 4- [3- (4-chlorophenyl) -2-propenyloxy] piperidine tert-butyl 4- [3- (4-chlorophenyl) -2-propenyloxy] piperidine-1-carboxylic acid prepared in Reference Example 112 A brown liquid 4- [3- (4-chlorophenyl) -2-propenyloxy] piperidine (0.291 g, quantitative) in the same manner as in Reference Example 111 using the ester (0.350 g, 0.995 mmol) I got
¹ H-NMR (CDCl ₃ ) δ ppm:
1.38-1.56 (2H, m), 1.9 1-2.01 (2H, m), 2.55-2.69 (2H, m), 3.11 (2H, ddd, J = 4 .0 Hz, 4.0 Hz, 13.0 Hz), 3.39-3.51 (1 H, m), 4.18 (2 H, d, J = 5.8 Hz), 6.28 (1 H, ddd, J = 5.8 Hz, 5.8 Hz, 15.9 Hz), 6.57 (1 H, d, J = 15.9 Hz), 7.25-7.35 (4 H, m).

Reference Example 114
Preparation of 4- [3- (4-chlorophenyl) propoxy] piperidine-1-carboxylic acid tert-butyl ester 4- [3- (4-chlorophenyl) -2-propenyloxy] piperidine-1- 1 prepared in Reference Example 112 Carboxylic acid tert-butyl ester (0.37 g, 1.05 mmol) was dissolved in ethanol (10 ml), and atmospheric pressure catalytic reduction was carried out at room temperature using platinum oxide (37 mg) as a catalyst. The reaction solution was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane / ethyl acetate = 4/1) to obtain 4- [3- (4-chlorophenyl) propoxy] piperidine-1-carboxylic acid tert-butyl ester (0. 6) as a yellow liquid. 151 g (yield 40%) were obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.40-1.51 (2H, m), 1.46 (9H, s), 1.77-1.90 (4H, m), 2.67 (2H, t, J = 7.9 Hz), 3.02-3.12 (2H, m), 3.38-3.45 (3H, m), 3.73-3.79 (2H, m), 7.11 (2H, d, J = 8) .4 Hz), 7.24 (2 H, d, J = 8.4 Hz).

Reference Example 115
Preparation of 4- [3- (4-chlorophenyl) propoxy] piperidine The 4- [3- (4-chlorophenyl) propoxy] piperidine-1-carboxylic acid tert-butyl ester prepared in Reference Example 114 (0.151 g, 0 .427 mmol) was dissolved in methylene chloride (4 ml), trifluoroacetic acid was added and stirred overnight at room temperature. The solution was made alkaline with aqueous sodium hydroxide solution and then extracted twice with methylene chloride. The organic phases were combined and washed with brine. The organic phase was dried over sodium sulfate and filtered. The obtained filtrate was concentrated under reduced pressure and dried under reduced pressure to obtain 4- [3- (4-chlorophenyl) propoxy] piperidine as a brown liquid (0.109 g, yield 92%).
¹ H-NMR (CDCl ₃ ) δ ppm:
1.35 to 1.51 (2H, m), 1.83 to 1.94 (4H, m), 2.54 to 2.70 (4H, m), 3.03 to 3.14 (2H, m) ), 3.22-3.38 (1 H, m), 3.43 (2 H, t, J = 6.3 Hz), 7. 12 (2 H, d, J = 8.4 Hz), 7.25 (2 H) , D, J = 8.4 Hz).

Reference Example 116
4- [2- (4-Chlorophenyl) ethoxy] piperidine-1-carboxylic acid tert-butyl ester (4-chlorobenzyl) -triphenyl-phosphonium chloride (1.191 g, 2.81 mmol) in DMSO (20 ml) It melt | dissolved, under ice-cooling sodium hydride (0.118 g, 2.95 mmol) was added, and it stirred at room temperature for 1 hour. The 4-formyloxy piperidine 1-carboxylic acid tert- butyl ester (0.500 g, 2.34 mmol) was added there, and it stirred at room temperature overnight. After extraction with ethyl acetate, the organic phases were combined and washed with water and brine. The organic phase was dried over sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride / hexane = 9/1) to give a colorless liquid.

Using the obtained liquid, a colorless liquid of 4- [2- (4-chlorophenyl) ethoxy] piperidine-1-carboxylic acid tert-butyl ester (0.127 g, yield 16%) by a method similar to Reference Example 114 Got).
¹ H-NMR (CDCl ₃ ) δ ppm:
1.40-1.51 (2H, m), 1.45 (9 H, s), 1.71-1. 79 (2 H, m), 2.83 (2 H, t, J = 6.9 Hz), 3.02-3.13 (2H, m), 3.38-3.44 (1H, m), 3.62-3.75 (4H, m), 7.15 (2H, d, J = 8) .5 Hz), 7.25 (2 H, d, J = 8.5 Hz).

Reference Example 117
Preparation of 4- [2- (4-chlorophenyl) ethoxy] piperidine 4- [2- (4-Chlorophenyl) ethoxy] piperidine-1-carboxylic acid tert-butyl ester (0.127 g, 0. 1) prepared in Reference Example 116. Using 374 mmol) and according to the same manner as in Reference Example 115, colorless liquid 4- [2- (4-chlorophenyl) ethoxy] piperidine (0.080 g, yield 89%) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.37-1.48 (2H, m), 1.84-1.91 (2H, m), 2.53-2.63 (2H, m), 2.83 (2H, t, J = 7 .0 Hz), 3.01 to 3.09 (2 H, m), 3.25 to 3.41 (1 H, m), 3.64 (2 H, t, J = 7.0 Hz), 7.15 (2 H) , D, J = 8.4 Hz), 7. 25 (2 H, d, J = 8.4 Hz).

Reference Example 118
Preparation of 1- (2-nitrovinyl) -4-trifluoromethylbenzene 4-Trifluoromethylbenzaldehyde (3.00 g, 17.2 mmol) was dissolved in nitromethane (10 ml) and ammonium acetate (1.341 g, 17.4). The mixture was heated to reflux for 2 hours. Water was added and the mixture was extracted with methylene chloride, and the organic phases were combined and washed with saturated brine. The organic phase was dried over magnesium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane / ethyl acetate = 9/1) to give 1- (2-nitrovinyl) -4-trifluoromethylbenzene (1.596 g, yield 43%) as a slightly yellow solid. I got
¹ H-NMR (CDCl ₃ ) δ ppm:
7.58-7.74 (5 H, m), 8.02 (1 H, d, J = 13.8 Hz).

Reference Example 119
Preparation of 2- (4-trifluoromethylphenyl) ethylamine Lithium aluminum hydride (0.558 g, 14.7 mmol) was suspended in THF (10 ml). A solution of 1- (2-nitrovinyl) -4-trifluoromethylbenzene (1.596 g, 7.35 mmol) prepared in Reference Example 118 dissolved in THF (10 ml) was added dropwise thereto under ice-cooling for 2 hours. Heated to reflux. Methanol was added slowly until bubbling ceased. Water (0.6 ml), 15% aqueous sodium hydroxide solution (0.6 ml) and water (1.8 ml) were sequentially added, and the precipitate was filtered off. The filtrate is concentrated under reduced pressure, and the obtained residue is purified by silica gel column chromatography (basic silica gel, methylene chloride / n-hexane = 4/1) to give orange liquid 2- (4-trifluoromethylphenyl) ethylamine (0.431 g, 31% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
2.81 (2H, t, J = 6.9 Hz), 3.03 (2 H, t, J = 6.9 Hz), 7.32 (2 H, d, J = 8.0 Hz), 7.56 (2 H , D, J = 8.0 Hz).

Reference Example 120
Preparation of N- (1-benzylpiperidin-4-yl) -N- [2- (4-trifluoromethylphenyl) ethyl] carbamic acid tert-butyl ester 2- (4-trifluoromethyl) prepared in Reference Example 119 Phenyl) ethylamine (0.431 g, 2.28 mmol) and 1-benzyl-4-piperidone (0.517 g, 2.73 mmol) are dissolved in methanol (15 ml) and sodium cyanoborohydride (0.429 g) , 6.83 mmol) and acetic acid (0.52 ml, 9.11 mmol) were added and stirred at room temperature overnight. After concentration under reduced pressure, extraction was performed with ethyl acetate. The organic phases were combined and washed with saturated aqueous sodium bicarbonate solution and saturated brine. The organic phase was dried over sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was dissolved in methanol (5 ml), di-tert-butyl dicarbonate (0.597 g, 2.74 mmol) was added and stirred overnight at room temperature. The mixture was extracted with ethyl acetate, and the organic phases were combined and washed with brine. The organic phase was dried over sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (n-hexane / ethyl acetate = 3/1) to give N- (1-benzylpiperidin-4-yl) -N- [2- (4-trifluoromethylphenyl) as a colorless liquid ) Ethyl] carbamic acid tert-butyl ester (0.437 g, 41% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.55 (9 H, s), 1.59-1.73 (4 H, m), 1.90-2.10 (2 H, m), 2.82-2.96 (4 H, m), 24-3.28 (2H, m), 3.49 (2H, s), 4.00 (1 H, bs), 7.26-7.31 (7 H, m), 7.54 (2 H, d, 2) J = 8.0 Hz).

Reference Example 121
Preparation of N- (Piperidin-4-yl) -N- [2- (4-trifluoromethylphenyl) ethyl] carbamic acid tert-butyl ester N- (1-benzylpiperidin-4-yl prepared in Reference Example 120 ) -N- [2- (4-Trifluoromethylphenyl) ethyl] carbamic acid tert-butyl ester (0.437 g, 0.944 mmol) is dissolved in ethanol (20 ml), 20% palladium hydroxide / carbon ( Atmospheric pressure catalytic reduction was carried out at room temperature using 100 mg of the catalyst as a catalyst. The reaction solution is filtered through Celite, and the filtrate is concentrated under reduced pressure to give colorless liquid N- (piperidin-4-yl) -N- [2- (4-trifluoromethylphenyl) ethyl] carbamic acid tert-. The butyl ester (0.332 g, 94% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.49 (9 H, s), 1.51-1. 80 (4 H, m), 2.62-3.49 (9 H, m), 7.28-7.31 (2 H, m), 7. 54 (2H, d, J = 8.0 Hz).

Reference Example 122
Preparation of 4- (4-Trifluoromethylbenzyloxy) piperidine-1-carboxylic acid tert-butyl ester 4-hydroxypiperidine-1-carboxylic acid tert-butyl ester (1.88 g, 9.34 mmol) in THF (20 ml) Dissolved in To this solution was added sodium hydride (411 mg, 10.3 mmol) under ice cooling, and the mixture was stirred for 1 hour. To this mixture 4- (trifluoromethyl) benzyl bromide (2.23 g, 9.34 mmol) was added and stirred at room temperature for 2 hours. Water was added to the reaction solution and extracted with methylene chloride. The extract was dried over magnesium sulfate and filtered, and the obtained filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride / methanol = 100/1) to give 4- (4-trifluoromethylbenzyloxy) piperidine-1-carboxylic acid tert-butyl ester (2.56 g) as pale yellow oil. , Yield 76%).
¹ H-NMR (CDCl ₃ ) δ ppm:
1.46 (9H, s), 1.51-1.67 (2H, m), 1.83-1.91 (2H, m), 3.07-3.18 (2H, m), 3. 52-3.63 (1 H, m), 3.73-3.83 (2 H, m), 4.61 (2 H, m), 7.46 (2 H, d, J = 8.2 Hz), 7. 60 (2H, d, J = 8.2 Hz).

  The compound of Reference Example 123 was produced in the same manner as in Reference Example 122 using the corresponding starting materials.

Reference Example 123
4- (4-Trifluoromethoxybenzyloxy) piperidine-1-carboxylic acid tert-butyl ester pale yellow oil, yield 74%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.46 (9H, s), 1.51-1.65 (2H, m), 1.82-1.90 (2H, m), 3.06-3.17 (2H, m), 3. 52-3.62 (1H, m), 3.73-3.83 (2H, m), 4.54 (2H, s), 7.17-7.20 (2H, m), 7.35- 7.38 (2H, m).

Reference Example 124
Preparation of 4- (4-trifluoromethylbenzyloxy) piperidine 4- (4-trifluoromethylbenzyloxy) piperidine-1-carboxylic acid tert-butyl ester (2.56 g, 7.12 mmol) prepared in Reference Example 122 ) Was dissolved in methylene chloride (20 ml). Under room temperature, trifluoroacetic acid (10 ml) was added dropwise and stirred for 5 hours. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in methylene chloride again. The solution was made alkaline with aqueous sodium hydroxide solution and extracted with methylene chloride. The organic phase was washed with brine, dried over magnesium sulfate and filtered. The obtained filtrate was concentrated under reduced pressure to give 4- (4-trifluoromethylbenzyloxy) piperidine (1.85 g, yield 99%) as a white powder.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.46 to 1.60 (2H, m), 1.87 (1H, s), 1.93 to 2.01 (2H, m), 2.58 to 2.69 (2H, m), 07-3.16 (2H, m), 3.43-3.54 (1H, m), 4.61 (2H, s), 7.44-7.48 (2H, m), 7.57- 7.61 (2H, m).

  The compounds of Reference Examples 125 to 128 were produced in the same manner as in Reference Example 124 using the corresponding starting materials.

Reference Example 125
4- (4-Trifluoromethoxybenzyloxy) piperidine white powder, yield 74%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.41 to 1.60 (2H, m), 1.92 to 2.02 (2H, m), 2.11 (1H, s), 2.59 to 2.70 (2H, m), 07-3.17 (2H, m), 3.43-3.54 (1 H, m), 4.55 (2 H, s), 7.17-7.20 (2 H, m), 7.35- 7.40 (2H, m).

Reference Example 126
4- (4-Chlorobenzyloxy) piperidine white powder, 94% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
1.39-1.56 (3H, m), 1.90-1.99 (2H, m), 2.55-2.66 (2H, m), 3.06-3.11 (2H, m) ), 3.39-3.51 (1 H, m), 4.52 (2 H, s), 7.25-7.33 (4 H, m).

Reference Example 127
4- (3,4-Dichlorobenzyloxy) piperidine white powder, yield 99%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.41 to 1.60 (2H, m), 1.91 to 2.01 (2H, m), 2.19 (1H, s), 2.59 to 2.70 (2H, m), 3. 07-3.16 (2 H, m), 3.42-3.52 (1 H, m), 4.50 (2 H, s), 7.17 (1 H, dd, J = 1.9 Hz, 8.2 Hz ), 7.40 (1 H, d, J = 8.2 Hz), 7. 45 (1 H, d, J = 1.9 Hz).

Reference Example 128
4- (4-phenylbenzyloxy) piperidine white powder, 16% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
1.45 to 1.60 (2H, m), 1.72 (1H, s), 1.95 to 2.02 (2H, m), 2.57 to 2.68 (2H, m), 3. 07-3.16 (2H, m), 3.45-3.56 (1H, m), 4.60 (2H, s), 7.25-7.60 (9H, m).

Reference Example 129
Preparation of (1-benzylpiperidin-4-yl)-(4-trifluoromethoxyphenyl) amine 1-bromo-4-trifluoromethoxybenzene (2.0 g, 8.3 mmol), 4-amino-1-benzyl Piperidine (1.73 g, 9.13 mmol), palladium acetate (37 mg, 0.17 mmol), (R)-(+)-BINAP (155 mg, 0.25 mmol) and tert-butoxy sodium (1.2 g, 11.6 mmol) was heated to reflux for 5 hours in toluene (30 ml) under a nitrogen atmosphere. Ethyl acetate and water were added to the reaction solution and the mixture was stirred, and the precipitate was removed by celite filtration, and the filtrate was extracted with ethyl acetate. The organic phase was washed with brine, dried over magnesium sulfate and filtered. The obtained filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (methylene chloride / methanol = 100/1) to give (1-benzylpiperidin-4-yl)-(4-trifluoromethoxy) as a black oil. Phenyl) amine (3.0 g, 99% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.39-1.55 (2H, m), 1.98-2.05 (2H, m), 2.09-2.20 (2H, m), 2.80-2.89 (2H, m) ), 3.21-3.28 (1 H, m), 3.52 (2 H, s), 3.52-3.59 (1 H, m), 6.48-6.55 (2 H, m), 6.98-7.02 (2H, m), 7.22-7.33 (5H, m).

Reference Example 130
Preparation of piperidin-4-yl- (4-trifluoromethoxyphenyl) amine (1-benzylpiperidin-4-yl)-(4-trifluoromethoxyphenyl) amine (3.0 g, 8.3 mmol) in ethanol The mixture was dissolved in 30 ml), a catalytic amount of 10% palladium / carbon was added, and the mixture was heated to reflux under a hydrogen atmosphere for 20 hours. The reaction solution was filtered through celite, and the obtained filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / methanol = 10/1) to give piperidin-4-yl- (4-trifluoromethoxyphenyl) amine (2.02 g, yield 94%) as a colorless solid. The
¹ H-NMR (CDCl ₃ ) δ ppm:
1.24-1.39 (2H, m), 2.03-2.08 (2H, m), 2.65-2.77 (2H, m), 3.08-2.16 (2H, m) ), 3.24 to 3.41 (1H, m), 3.59 (1H, br), 6.50 to 6.58 (2H, m), 6.99 to 7.03 (2H, m).

Reference Example 131
Preparation of 4- (4-chlorophenylamino) piperidine-1-carboxylic acid tert-butyl ester p-bromochlorobenzene (1.91 g, 9.99 mmol), 4-aminopiperidine-1-carboxylic acid tert-butyl ester (2 .0 g, 9.99 mmol), palladium acetate (45 mg, 0.2 mmol), (R)-(+)-BINAP (187 mg, 0.3 mmol) and tert-butoxy sodium (1.35 g, 14.0) The mmol) was heated to reflux for 1 hour in toluene (20 ml) under a nitrogen atmosphere. Ethyl acetate and water were added to the reaction solution and the mixture was stirred, and the precipitate was removed by celite filtration, and the filtrate was extracted with ethyl acetate. The organic phase was washed with brine, dried over magnesium sulfate and filtered. The obtained filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (methylene chloride / methanol = 100/1) to obtain 4- (4-chlorophenylamino) piperidine-1-carboxylic acid tert-butyl ester as a yellow powder. (2.67 g, 86% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.21-1.54 (2H, m) 1.46 (9H, s), 1.99-2.05 (2H, m), 2.85-2.97 (2H, m), 3.37 (1H, br), 3.51 (1H, br), 4.01 to 4.07 (2H, m), 6.48 to 6.54 (2H, m), 7.07 to 7.14 (2H) , M).

  The compounds of Reference Example 132 to Reference Example 133 were produced in the same manner as in Reference Example 131 using the corresponding starting materials.

Reference Example 132
4- (4-Trifluoromethylphenylamino) piperidine-1-carboxylic acid tert-butyl ester yellow powder, 93% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
1.21-1.58 (2H, m), 1.47 (9H, s), 2.00-2.06 (2H, m), 2.88-2.99 (2H, m), 3. 47 (1 H, br), 3.88 (1 H, bs), 4.03-4.09 (1 H, m), 6.56 (2 H, d, J = 8.6 Hz), 7.39 (2 H, d, J = 8.6 Hz).

Reference Example 133
4- (4-Cyanophenylamino) piperidine-1-carboxylic acid tert-butyl ester yellow powder, 92% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
1.26 to 1.54 (2H, m), 1.47 (9H, s), 1.99 to 2.05 (2H, m), 2.87 to 2.99 (2H, m), 3. 41-3.53 (1H, br), 4.02-4.14 (3H, m), 6.52-6.58 (2H, m), 7.39-7. 45 (2H, m).

Reference Example 134
Preparation of 4- (4-chlorophenylamino) piperidine 4- (4-chlorophenylamino) piperidine-1-carboxylic acid tert-butyl ester (2.67 g, 8.59 mmol) prepared in Reference Example 131 in methylene chloride (20 ml) Dissolved in Trifluoroacetic acid (15 ml) was added dropwise at room temperature and stirred for 5 hours. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in methylene chloride again. The reaction solution was made alkaline with aqueous sodium hydroxide solution and extracted with methylene chloride. The organic phase was washed with brine, dried over magnesium sulfate and filtered. The obtained filtrate was concentrated under reduced pressure to obtain 4- (4-chlorophenylamino) piperidine (1.76 g, yield 97%) as pale yellow powder.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.22-1.38 (2H, m), 2.02-2.07 (2H, m), 2.65-2.76 (2H, m), 3.08-3.16 (2H, m) ), 3.25 to 3.38 (1 H, m), 3.50 to 3.54 (1 H, m), 6.48 to 6.55 (2 H, m), 7.06 to 7.26 (2 H) , M).

  The compounds of Reference Examples 135 to 136 were produced in the same manner as in Reference Example 134 using the corresponding starting materials.

Reference Example 135
4- (4-Trifluoromethylphenylamino) piperidine yellow powder, 97% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
1.26-1.42 (2H, m), 2.04-2.09 (2H, m), 2.67-2.78 (2H, m), 3.09-3. 17 (2H, m) ), 3.33-3.46 (1 H, m), 3.86-3.90 (1 H, m), 6.59 (2 H, d, J = 8.6 Hz), 7.38 (2 H, d) , J = 8.6 Hz).

Reference Example 136
4- (4-Cyanophenylamino) piperidine yellow powder, yield 98%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.27-1.45 (2H, m), 2.02-2.07 (2H, m), 2.67-2.78 (2H, m), 3.09-3.17 (2H, m) ), 3.33-3.46 (1 H, m), 4.09-4.13 (1 H, m), 6.51-6.57 (2 H, m), 7.38-7.44 (2 H) , M).

Reference Example 137
Preparation of 4- (toluene-4-sulfonyloxy) piperidine-1-carboxylic acid tert-butyl ester 4-hydroxypiperidine-1-carboxylic acid tert-butyl ester (2.22 g, 10.0 mmol) in acetonitrile (40 ml) Solution in this solution and triethylamine (2.74 ml, 19.7 mmol) and N, N, N ', N'-tetramethyl-1,6-diaminohexane (0.57 ml, 2.64 mmol) in this solution. Add ice cold. To this mixture was added p-toluenesulfonyl chloride (2.75 g, 14.4 mmol) and stirred overnight with warming to room temperature. The reaction solution was poured into water and extracted with diethyl ether. The organic phase was washed with brine, dried over magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride / methanol = 100/1) to give 4- (toluene-4-sulfonyloxy) piperidine-1-carboxylic acid tert-butyl ester (4.16 g, pale yellow powder) Rate of 89%).
¹ H-NMR (CDCl ₃ ) δ ppm:
1.44 (9H, s), 1.64-1.82 (4H, m), 2.44 (3H, s), 3.19-3. 30 (2H, m), 3.54-3. 64 (2H, m), 4.63-4.72 (1 H, m), 7.31-7.37 (2 H, m), 7.78-7.82 (2 H, m).

Reference Example 138
Preparation of 4- (4-trifluoromethoxyphenylsulfanyl) piperidine-1-carboxylic acid tert-butyl ester 4- (trifluoromethoxy) thiophenol (2.0 g, 10.3 mmol) was dissolved in THF (30 ml) Ice cooled. After adding sodium hydride (453 mg, 11.3 mmol) and stirring for 30 minutes, 4- (toluene-4-sulfonyloxy) piperidine-1-carboxylic acid tert-butyl ester (3.66 g) prepared in Reference Example 137 10.3 mmol) was added and stirred at room temperature for 30 minutes and then heated to reflux for 1 hour. Water was added to the reaction solution and extracted with methylene chloride. The organic phase was dried over magnesium sulfate and filtered, and the obtained filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane / ethyl acetate = 20/1). There was obtained 4- (4-trifluoromethoxyphenylsulfanyl) piperidine-1-carboxylic acid tert-butyl ester (3.12 g, yield 80%) as a colorless oil.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.45 (9H, s), 1.46 to 1.60 (2H, m), 1.87 to 1.95 (2H, m), 2.86 to 2.98 (2H, m), 14-3. 23 (1 H, m), 3.94-4.00 (2 H, m), 7. 13-7. 17 (2 H, m), 7. 40-7. 47 (2 H, m).

Reference Example 139
Preparation of 4- (4-trifluoromethoxyphenylsulfanyl) piperidine By using 4- (4-trifluoromethoxyphenylsulfanyl) piperidine-1-carboxylic acid tert-butyl ester prepared in Reference Example 138 in the same manner as in Reference Example 134 As a result, 4- (4-trifluoromethoxyphenylsulfanyl) piperidine (yield 92%) as a colorless oil was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.43-1.59 (2H, m), 1.91-1.98 (2H, m), 2.59-2.70 (2H, m), 3.06-3.20 (3H, m) ], 7.12-7.16 (2H, m), 7.40-7.46 (2H, m).

Reference Example 140
Preparation of 4- (4-trifluoromethoxybenzyl) piperidine-1-carboxylic acid tert-butyl ester Triphenyl- (4-trifluoromethoxybenzyl) phosphonium bromide (2.0 g, 3.87 mmol) was dissolved in DMSO Then, sodium hydride was added and stirred for 30 minutes. 4-oxopiperidine-1-carboxylic acid tert-butyl ester (700 mg, 3.51 mmol) was added and stirred at 60 ° C. for 2 hours. The reaction solution was poured into water and extracted with diethyl ether. The organic phase was washed with brine, dried over magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride / methanol = 100/1) to give a white solid.

The white solid was dissolved in methanol, a catalytic amount of 10% Pd-C was added, and the mixture was stirred at room temperature for 3 hours under a hydrogen atmosphere. The reaction solution is filtered, and the obtained filtrate is concentrated under reduced pressure to give 4- (4-trifluoromethoxybenzyl) piperidine-1-carboxylic acid tert-butyl ester (1.28 g, yield) as a colorless oil. 60%).
¹ H-NMR (CDCl ₃ ) δ ppm:
1.06-1.21 (2H, m), 1.45 (9 H, s), 1.57-1.70 (3 H, m), 2.52-2. 69 (4 H, m), 4.. 08 (2H, br), 7.09-7. 17 (4H, m).

Reference Example 141
Preparation of 4- (4-trifluoromethoxybenzyl) piperidine Using 4- (4-trifluoromethoxybenzyl) piperidine-1-carboxylic acid tert-butyl ester prepared in Reference Example 140, in the same manner as in Reference Example 134, 4- (4-Trifluoromethoxybenzyl) piperidine was prepared.
Colorless solid, 99% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
1.06-1.22 (2H, m), 1.50 (1 H, s), 1.53-1.68 (3 H, m), 2.48-2.60 (4 H, m), 3. 02-3.08 (2H, m), 7.09-7. 17 (4H, m).

Reference Example 142
Preparation of 1-benzyl-4- (4-trifluoromethoxybenzylidene) piperidine Triphenyl- (4-trifluoromethoxybenzyl) -phosphonium bromide (21.6 g, 41.75 mmol) was dissolved in DMSO and sodium hydride (1.82 g, 45.52 mmol) was added and stirred for 30 minutes. 1-benzyl-4-piperidone (7.18 g, 37.96 mmol) was added and stirred at 60 ° C. for 2 hours. The reaction solution was poured into ice water and extracted with ethyl acetate. The organic phase was washed with brine, dried over magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 10/1) to give 1-benzyl-4- (4-trifluoromethoxybenzylidene) piperidine (9.75 g, yield 74%) as a yellow oil. I got
¹ H-NMR (CDCl ₃ ) δ ppm:
2.36-2.55 (8 H, m), 3.53 (2 H, s), 6.23 (1 H, s), 7.1 1-7.34 (9 H, m).

  The compound of Reference Example 143 was produced in the same manner as in Reference Example 142 using the corresponding starting materials.

Reference Example 143
1-Benzyl-4- (4-trifluoromethylbenzylidene) piperidine yellow oil, yield 52%
¹ H-NMR (CDCl ₃ ) δ ppm:
2.38-2.57 (8 H, m), 3.53 (2 H, s), 6.28 (1 H, m), 7.24-7.56 (9 H, m).

Reference Example 144
Preparation of 4- (4-trifluoromethoxybenzyl) piperidine (Another synthesis method of the compound of Reference Example 141)
1-Benzyl-4- (4-trifluoromethoxybenzylidene) piperidine (9.7 g, 27.92 mmol) was dissolved in ethanol (100 ml), 6N hydrochloric acid (9.3 ml) was added, and ice-cooled. 10% Palladium / carbon (970 mg) was added, and the mixture was stirred at 50 ° C. for 5 hours under a hydrogen atmosphere. The reaction solution was filtered through Celite, and the obtained filtrate was concentrated under reduced pressure. Water and 10% aqueous sodium hydroxide solution were added to the residue, and the mixture was extracted with methylene chloride. The organic phase was washed with brine, dried over magnesium sulfate and filtered. The obtained filtrate was concentrated under reduced pressure to give 4- (4-trifluoromethoxybenzyl) piperidine (6.77 g, yield 94%) as a colorless solid.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.06-1.22 (2H, m), 1.50 (1 H, s), 1.53-1.68 (3 H, m), 2.48-2.60 (4 H, m), 3. 02-3.08 (2H, m), 7.09-7. 17 (4H, m).

  The compounds of Reference Example 145 and Reference Example 146 were produced in the same manner as in Reference Example 144 using the corresponding starting materials.

Reference Example 145
4- (4-Trifluoromethylbenzyl) piperidine white solid, 94% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
1.06-1.29 (2H, m), 1.50-1.69 (4H, m), 2.48-2.60 (4H, m), 3.02-3.09 (2H, m) ), 7.23-7.29 (2H, m), 7.51-7.54 (2H, m).

Reference Example 146
4- (4-Chlorobenzyl) piperidine white solid, yield 94%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.07-1.21 (2H, m), 1.53-1.82 (4H, m), 2.47-2.59 (4H, m), 3.02-3.08 (2H, m) ), 7.04-7.08 (2H, m), 7.22-7.27 (2H, m).

Reference Example 147
Preparation of 1-benzylpiperidine-4-carboxylic acid N-methyl-N-methoxyamide 1-benzylpiperidine-4-carboxylic acid hydrochloride (21 g, 82.3 mmol) was suspended in chloroform, DMF (1 ml) at room temperature And thionyl chloride (30 ml) were added and heated to reflux for 2 hours. The mixture was concentrated under reduced pressure to adjust acid chloride.

In a separate container, N, O-dimethylhydroxylamine hydrochloride (12 g, 0.12 mol) is dissolved in acetone (200 ml) -water (20 ml) and potassium carbonate (34.12 g, 246.9 mmol) is added, It stirred under ice-cooling. The previous acetone solution (120 ml) of acid chloride was added dropwise thereto, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, water was added, and the mixture was extracted with methylene chloride. The organic phase was washed with brine, dried over magnesium sulfate and filtered. The obtained filtrate was concentrated under reduced pressure to obtain 1-benzylpiperidine-4-carboxylic acid N-methyl-N-methoxyamide (16.8 g, yield 78%) as a brown oil.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.65-1.92 (4H, m), 1.97-2.07 (2H, m), 2.62-2.68 (1H, m), 2.91-2.96 (2H, m) ), 3.17 (3H, s), 3.51 (2H, s), 3.69 (3H, s), 7.20-7. 32 (5H, m).

Reference Example 148
Preparation of 1-benzyl-4- (4-trifluoromethoxybenzoyl) piperidine 1-bromo-4-trifluoromethoxybenzene (5.3 g, 22.0 mmol) was dissolved in dry THF (70 ml) under nitrogen atmosphere. It cooled and stirred at -60 degreeC. n-Butyllithium (1.6 M) hexane solution (15 ml, 24.0 mmol) was added dropwise, and the mixture was stirred for 1 hour while warming up to -30 ° C. After cooling again to -60 ° C, a solution of 1-benzylpiperidine-4-carboxylic acid N-methyl-N-methoxyamide (4.1 g, 15.6 mmol) prepared in Reference Example 147 in THF (10 ml) was added dropwise. The mixture was stirred at the same temperature for 1 hour and at 0 ° C. for 3 hours. The reaction solution was poured into ice-saturated aqueous ammonium chloride solution and extracted with diethyl ether. The organic phase was washed with water and brine, dried over magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane / ethyl acetate = 4/1) to give 1-benzyl-4- (4-trifluoromethoxybenzoyl) piperidine (4.8 g, yield 85) as a pale yellow oil. %) Got.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.80-1.89 (4H, m), 2.04-2.18 (2H, m), 2.94-3.01 (2H, m), 3.15-3.24 (1 H, m) ), 3.55 (2 H, s), 7.19-7.34 (7 H, m), 7.95-8.01 (2 H, m).

  The compound of Reference Example 149 was produced in the same manner as in Reference Example 148 using the corresponding starting materials.

Reference Example 149
1-Benzyl-4- (4-trifluoromethylbenzoyl) piperidine pale yellow oil, yield 66%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.78-1.89 (4H, m), 2.09-2.19 (2H, m), 2.94-3.02 (2H, m), 3.16-3. 29 (1 H, m) ), 3.55 (2H, m), 7.26-7.34 (5H, m), 7. 70-7. 74 (2H, m), 8.00-8. 04 (2H, m).

Reference Example 150
Preparation of 4- (4-trifluoromethoxybenzoyl) piperidine 1-benzyl-4- (4-trifluoromethoxybenzoyl) piperidine (4.8 g, 13.22 mmol) prepared in Reference Example 148 in methylene chloride (60 ml) In ice and cooled on ice. 1-Chloroethyl chloroformate (2.9 ml, 26.4 mmol) was added dropwise and stirred at the same temperature for 30 minutes. The reaction solution was concentrated under reduced pressure, methanol (100 ml) was added to the residue, and the mixture was heated to reflux for 15 minutes. Water was added to the reaction solution, and the mixture was stirred for 30 minutes, made alkaline with sodium hydroxide, and extracted with methylene chloride. The organic phase was washed with brine, dried over magnesium sulfate and filtered. The obtained filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (n-hexane / ethyl acetate = 1/1) to give 4- (4-trifluoromethoxybenzoyl) piperidine (light orange solid) 1.3 g, 36% yield) were obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.57-1.88 (5H, m), 2.71-2.81 (2H, m), 3.15-3. 23 (2H, m), 3.29-3. 42 (1 H, m) ), 7.27-7.28 (2H, m), 7.95-8.05 (2H, m).

  The compounds of Reference Example 151 and Reference Example 152 were produced in the same manner as in Reference Example 150 using the corresponding starting materials.

Reference Example 151
4- (4-Trifluoromethylbenzoyl) piperidine white solid, yield 68%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.61-1.76 (3H, m), 1.82-1.89 (2H, m), 2.72-2.83 (2H, m), 3.16-3.24 (2H, m) ), 3.32-3.44 (1 H, m), 7.72-7. 76 (2 H, m), 8.01-8. 05 (2 H, m).

Reference Example 152
4- (4-Chlorobenzoyl) piperidine white solid, 100% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
1.60-1.84 (5 H, m), 2.72-2.83 (2 H, m), 3.16-3. 24 (2 H, m), 3.30-3. 40 (1 H, m) ), 7.41 to 7.47 (2H, m), 7.85 to 7.91 (2H, m).

Reference Example 153
Preparation of N- {2- [4- (4-Trifluoromethylphenyl) piperazin-1-yl] ethyl} phthalimide 1- (4-Trifluoromethylphenyl) piperazine (5.2 g, 22.59 mmol), N -(2-Bromoethyl) phthalimide (5.22 g, 20.53 mmol) and potassium carbonate (3.36 g, 24.28 mmol) were stirred in DMF (30 ml) at 100 ° C. for 2 hours. The reaction solution was cooled, water was added, and the mixture was extracted with ethyl acetate. The organic phase was washed with brine, dried over magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue is separated and purified by silica gel column chromatography (methylene chloride / ethyl acetate = 50/1), and the obtained crystals are washed with methanol and then dried under reduced pressure to obtain N- {2- [4- (white powder)]. 4-trifluoromethylphenyl) piperazin-1-yl] ethyl} phthalimide (4.85 g, yield 53%) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
2.64-2.72 (6H, m), 3.18-3.23 (4H, m), 3.86 (2H, t, J = 6.4 Hz), 6.89 (2H, d, J = 8.7 Hz), 7.45 (2 H, d, J = 8.7 Hz), 7. 70-7. 75 (2 H, m), 7.8 1-7. 86 (2 H, m).

Reference Example 154
Preparation of 2- [4- (4-trifluoromethylphenyl) piperazin-1-yl] ethylamine N- {2- [4- (4-trifluoromethylphenyl) piperazin-1-yl] prepared in Reference Example 153 Ethyl} phthalimide (4 g, 9.92 mmol) was suspended in ethanol (30 ml), hydrazine monohydrate (0.53 ml, 10.91 mmol) was added and the mixture was heated to reflux and stirred for 5 hours. The reaction solution was cooled and the precipitate was collected by filtration. This is separated and purified by silica gel column chromatography (methylene chloride / ethyl acetate = 100/1) to give 2- [4- (4-trifluoromethylphenyl) piperazin-1-yl] ethylamine (2.87 g) as white crystals. , Yield 100%).
¹ H-NMR (CDCl ₃ ) δ ppm:
1.33 (2H, bs), 2.49 (2H, t, J = 6.1 Hz), 2.59-2.63 (4H, m), 2.84 (2H, t, J = 6.1 Hz ), 3.26-3.31 (4H, m), 6.92 (2H, d, J = 8.7 Hz), 7.48 (2 H, d, J = 8.7 Hz).

Reference Example 155
Preparation of N- {2- [4- (4-trifluoromethylphenyl) piperazin-1-yl] ethyl} formamide 2- [4- (4-trifluoromethylphenyl) piperazine-1 prepared in Reference Example 154 [Ethyl] ethylamine (906 mg, 3.32 mmol) in ethyl formate (10 ml) was heated to reflux for 5 hours. The reaction mixture is concentrated under reduced pressure, and the residue is separated and purified by silica gel column chromatography (methylene chloride / methanol = 100/1) to give N- {2- [4- (4-trifluoromethylphenyl) piperazine as a white powder. 1-yl] ethyl} formamide (942 mg, 94% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
2.53-2.65 (6H, m), 3.26-3. 31 (4H, m), 3.42-3.49 (2H, m), 6.05 (1 H, bs), 92 (2H, d, J = 8.7 Hz), 7.49 (2 H, d, J = 8.7 Hz), 8.21 (1 H, s).

Reference Example 156
Preparation of N-methyl- {2- [4- (4-trifluoromethylphenyl) piperazin-1-yl] ethyl} amine Lithium aluminum hydride (237 mg, 6.25 mmol) was suspended in THF (20 ml), It stirred under ice-cooling. Thereto was dropwise added a solution of N- {2- [4- (4-trifluoromethylphenyl) piperazin-1-yl] ethyl} formamide (942 mg, 3.13 mmol) prepared in Reference Example 155 in THF (10 ml). The mixture was stirred at room temperature for 2 hours and then heated under reflux for 2 hours. The reaction solution was cooled, and water and 15% aqueous sodium hydroxide solution were carefully added to terminate the reaction. Sodium sulfate was added and the mixture was vigorously stirred and filtered through celite. The filtrate was concentrated under reduced pressure to give N-methyl- {2- [4- (4-trifluoromethylphenyl) piperazin-1-yl] ethyl} amine (900 mg, 100% yield) as a yellow oily substance.
¹ H-NMR (CDCl ₃ ) δ ppm:
2.47 (3H, s), 2.52-2.74 (8H, m), 3.26-3.30 (4H, m), 3.71-3.77 (1 H, m), 6. 91 (2H, d, J = 8.7 Hz), 7.47 (2 H, d, J = 8.7 Hz).

Reference Example 157
Preparation of 4- (2-Methylaminoethyl) piperazine-1-carboxylic acid tert-butyl ester 4- (2-Chloroethyl) piperazine-1-carboxylic acid tert-butyl ester (3.13 g, 12.58 mmol) in methanol It was dissolved in (20 ml), methylamine methanol solution (30 ml) was added, and the mixture was heated to reflux for 5 hours. The reaction solution was concentrated under reduced pressure, diluted with methylene chloride and washed with saturated sodium bicarbonate. The organic phase is dried over magnesium sulfate and filtered, and the obtained filtrate is concentrated under reduced pressure to give 4- (2-methylaminoethyl) piperazine-1-carboxylic acid tert-butyl ester of a slightly yellow oily substance (3 .0 g, yield 98%).
¹ H-NMR (CDCl ₃ ) δ ppm:
1.46 (9H, m), 1.66 (1H, s), 2.36-2.41 (4H, m), 2.45 (3H, s), 2.46 to 2.53 (2H, 2H) m), 2.65-2.70 (2H, m), 3.40-3.44 (4H, m).

Reference Example 158
Preparation of N- [2- (4-Trifluoromethylphenoxy) ethyl] phthalimide N- (2-hydroxyethyl) phthalimide (3.59 g, 18.75 mmol), 4-hydroxybenzotrifluoride (3.04 g, 18 .75 mmol), diethyl azodicarboxylate (4.37 ml, 28.13 mmol) and triphenylphosphine (7.38 g, 28.13 mmol) were dissolved in THF (50 ml) and stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane / ethyl acetate = 5/1). White crystals of N- [2- (4-trifluoromethylphenoxy) ethyl] phthalimide (4.05 g, yield 69%) were obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
4.11-4.16 (2H, m), 4.25-4.30 (2H, m), 6.92-6.96 (2H, m), 7.48-7. 52 (2H, m) ], 7.72-7.77 (2H, m), 7.83-7.89 (2H, m).

Reference Example 159
Preparation of 2- (4-trifluoromethylphenoxy) ethylamine Using N- [2- (4-trifluoromethylphenoxy) ethyl] phthalimide prepared in Reference Example 158, in the same manner as in Reference Example 154, 2- (4 -Trifluoromethylphenoxy) ethylamine was obtained.
Colorless oil, 95% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
1.36 (2H, s), 3.11 (2H, t, J = 5.1 Hz), 4.03 (2H, t, J = 5.1 Hz), 6.97 (2H, d, J = 8 .6 Hz), 7.54 (2 H, d, J = 8.6 Hz).

Reference Example 160
Preparation of N- [2- (4-trifluoromethylphenoxy) ethyl] formamide Ethyl formate (10 ml) was prepared from 2- (4-trifluoromethylphenoxy) ethylamine (1.38 g, 6.72 mmol) prepared in Reference Example 159 ) Under reflux for 5 hours. The reaction mixture is concentrated under reduced pressure, and the residue is separated and purified by silica gel column chromatography (methylene chloride / methanol = 100/1) to give N- [2- (4-trifluoromethylphenoxy) ethyl] formamide (1 as a white powder) .51 g (97% yield) were obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
3.72-3.78 (2H, m), 4.09-4.13 (2H, m), 6.02 (1 H, bs), 6.96 (2 H, d, J = 8.6 Hz), 7.56 (2H, d, J = 8.6 Hz), 8.24 (1 H, s).

Reference Example 161
Preparation of N-methyl-N- [2- (4-trifluoromethylphenoxy) ethyl] amine N- [2- (4-trifluoromethylphenoxy) ethyl] formamide (2.02 g, 8) prepared in Reference Example 160 .66 mmol) was dissolved in THF (20 ml). Under ice cooling, a 1 M solution of borane-THF complex (21.7 ml, 21.7 mmol) was added dropwise and stirred overnight. The reaction solution was cooled, water and 6N hydrochloric acid were added, and the mixture was stirred for 20 minutes. The solution was made alkaline with sodium hydroxide aqueous solution and extracted with methylene chloride. The organic phase was dried over magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue is separated and purified by silica gel column chromatography (methylene chloride / methanol = 200/1) to give N-methyl-N- [2- (4-trifluoromethylphenoxy) ethyl] amine (1.05 g) as a white powder. , Yield 55%).
¹ H-NMR (CDCl ₃ ) δ ppm:
2.68 (3 H, d, J = 5.8 Hz), 3.05-3.28 (2 H, m), 4.06 (1 H, br), 4. 10-4. 18 (1 H, m), 4.45-4.54 (1 H, m), 6.98 (2 H, d, J = 8.5 Hz), 7.58 (2 H, d, J = 8.5 Hz).

Reference Example 162
Preparation of N-Methyl-N- [2- (4-Trifluoromethoxyphenoxy) ethyl] amine 1- (2-Bromoethoxy) -4-trifluoromethoxybenzene (2.2 g, 7.72 mmol) in methanol (2.2 g, 7.72 mmol) The solution was dissolved in 20 ml, 40% methylamine methanol solution (20 ml) was added, and the mixture was heated to reflux for 5 hours. The reaction solution was concentrated under reduced pressure, diluted with methylene chloride and washed with saturated sodium bicarbonate. The organic phase is dried over magnesium sulfate and filtered, and the filtrate obtained is concentrated under reduced pressure to give N-methyl-N- [2- (4-trifluoromethoxyphenoxy) ethyl] amine as a slightly yellow oily substance. (1.44 g, 79% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.54 (1 H, s), 2.51 (3 H, s), 2.97 (2 H, t, J = 5.1 Hz), 4.06 (2 H, t, J = 5.1 Hz), 6. 85-6.92 (2H, m), 7.10-7. 17 (2H, m).

Reference Example 163
Preparation of N-methyl-N- [2- (4-trifluoromethylphenoxy) ethyl] amine In the same manner as in Reference Example 162 using 1- (2-bromoethoxy) -4- (trifluoromethyl) benzene N-Methyl-N- [2- (4-trifluoromethylphenoxy) ethyl] amine was prepared.
White powder, 82% yield.
¹ H-NMR (CDCl ₃ ) δ ppm:
2.68 (3H, d, J = 5.8 Hz), 3.02-3.28 (2H, m), 3.92-4.18 (2H, m), 4.41-4.54 (1H) , M), 6.98 (2H, d, J = 8.5 Hz), 7.58 (2H, d, J = 8.5 Hz).

Reference Example 164
Preparation of N, N'-dimethyl-N- (4-trifluoromethylphenyl) -1,2-ethylenediamine 4-bromobenzotrifluoride (3.0 g, 13.3 mmol), N, N'-dimethylethylenediamine ( 9.4 g, 0.11 mol), palladium acetate (60 mg, 0.27 mmol), BINAP (250 mg, 0.40 mmol) and sodium tert-butoxy (1.80 g, 18.7 mmol) under a nitrogen atmosphere The mixture was heated to reflux for 3 hours in (20 ml). Ethyl acetate and water were added to the reaction solution, and the mixture was stirred, the precipitate was removed by Celite filtration, and the filtrate was extracted with ethyl acetate. The organic phase was washed with brine, dried over magnesium sulfate and filtered. The obtained filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (methylene chloride / methanol = 10/1) to give N, N'-dimethyl-N- (4-trifluoromethylphenyl) as a pale yellow oil. ) -1,2-ethylenediamine (650 mg, 21% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.53 (1 H, s), 2.47 (3 H, s), 2.82 (2 H, t, J = 6.7 Hz), 3.02 (3 H, s), 3.52 (2 H, t, J = 6.7 Hz), 6.74 (2 H, d, J = 8.8 Hz), 7.43 (2 H, d, J = 8.8 Hz).

Reference Example 165
Preparation of N- [1- (4-chlorophenyl) piperidin-4-yl] -N-methylcarbamic acid tert-butyl ester p-bromochlorobenzene (3.13 g, 16.3 mmol), (piperidin-4-yl)- N-Methylcarbamic acid tert-butyl ester (3.5 g, 10.8 mmol), palladium acetate (73 mg, 0.33 mmol), (S)-(-)-BINAP (305 mg, 0.49 mmol) and tert- Sodium butoxy (2.2 g, 22.9 mmol) was heated to reflux under toluene atmosphere in toluene (30 ml) for 3 hours. Ethyl acetate and water were added to the reaction solution, and the mixture was stirred, the precipitate was removed by Celite filtration, and the filtrate was extracted with ethyl acetate. The organic phase was washed with brine, dried over magnesium sulfate and filtered. The obtained filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 10/1) to obtain N- [1- (4-chlorophenyl) piperidin-4-yl] -yellow powder. N-methylcarbamic acid tert-butyl ester (4.7 g, 89% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.47 (9 H, s), 1. 70 -1. 90 (4 H, m), 2.7 3-2.8 2 (2 H, m), 2. 74 (3 H, s), 3.64-3. 71 (2H, m), 4.08 (1 H, br), 6.81-6.87 (2 H, m), 7.15-7.22 (2 H, m).

  The compounds of Reference Example 166 to Reference Example 168 were produced in the same manner as in Reference Example 165, using the corresponding starting materials.

Reference Example 166
N- [1- (4-Trifluoromethoxyphenyl) piperidin-4-yl] -N-methylcarbamic acid tert-butyl ester yield 88%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.48 (9H, s), 1.72-1.91 (4H, m), 2.76 (3H, s), 2.79-2.85 (2H, m), 3.67-3. 73 (2H, m), 4.10 (1 H, br), 6.86-6.93 (2 H, m), 7.07-7.11 (2 H, m).

Reference Example 167
Production yield of N- [1- (4-trifluoromethylphenyl) piperidin-4-yl] -N-methylcarbamic acid tert-butyl ester 91%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.47 (9H, s), 1.72-1.87 (4H, m), 2.74 (3H, s), 2.82-2.94 (2H, m), 3.83-3. 89 (2H, m), 4.12 (1 H, br), 6.92 (2 H, d, J = 8.7 Hz), 7.46 (2 H, d, J = 8.7 Hz).

Reference Example 168
Production yield of N- [1- (4-cyanophenyl) piperidin-4-yl] -N-methylcarbamic acid tert-butyl ester 73%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.47 (9H, s), 1.69-1.77 (4H, m), 2.73 (3H, s), 2.87-3.00 (2H, m), 3.89-3. 97 (2H, m), 4.16 (1 H, br), 6.84-6.89 (2 H, m), 7.45-7.51 (2 H, m).

Reference Example 169
Preparation of N- [1- (4-Chlorophenyl) piperidin-4-yl] -N-methylamine N- [1- (4-Chlorophenyl) piperidin-4-yl] -N-methylcarbamic acid prepared in Reference Example 165 The tert-butyl ester (4.71 g, 14.5 mmol) was dissolved in methylene chloride (30 ml). Under room temperature, trifluoroacetic acid (20 ml) was added dropwise and stirred for 5 hours. The reaction mixture was concentrated under reduced pressure, the residue was dissolved again in methylene chloride, made alkaline with aqueous sodium hydroxide solution, and extracted with methylene chloride. The organic phase was washed with brine, dried over magnesium sulfate and filtered. The obtained filtrate was concentrated under reduced pressure to obtain N- [1- (4-chlorophenyl) piperidin-4-yl] -N-methylamine (3.1 g, yield 95%) as a pale brown powder.
¹ H-NMR (CDCl ₃ ) δ ppm:
0.99 (1 H, s), 1.38-1.54 (2 H, m), 1.95-2.00 (2 H, m), 2.44-2.54 (1 H, m), 46 (3H, s), 2.71 to 2.82 (2H, m), 3.55 to 3.63 (2H, m), 6.81 to 6.87 (2H, m), 7.14- 7.21 (2H, m).

  The compounds of Reference Example 170 to Reference Example 172 were produced in the same manner as in Reference Example 169, using the corresponding starting materials.

Reference Example 170
N- [1- (4-Trifluoromethoxyphenyl) piperidin-4-yl] -N-methylamine light brown powder, yield 100%
¹ H-NMR (CDCl ₃ ) δ ppm:
0.96 (1 H, s), 1.39-1.55 (2 H, m), 1.96-2.02 (2 H, m), 2.44-2.57 (1 H, m), 47 (3H, s), 2.73-2.84 (2H, m), 3.58-3.66 (2H, m), 6.86-6.92 (2H, m), 7.05- 7.10 (2H, m).

Reference Example 171
N- [1- (4-Trifluoromethylphenyl) piperidin-4-yl] -N-methylamine light brown powder, yield 100%
¹ H-NMR (CDCl ₃ ) δ ppm:
0.96 (1 H, s), 1.36 to 1.52 (2 H, m), 1.96 to 2.02 (2 H, m), 2.47 (3 H, s), 2.50-2. 62 (1 H, m), 2.82-2.94 (2 H, m), 3.72-3.80 (2 H, m), 6.92 (2 H, d, J = 8.8 Hz), 7. 45 (2H, d, J = 8.8 Hz).

Reference Example 172
N- [1- (4-Cyanophenyl) piperidin-4-yl] -N-methylamine light brown powder, yield 99%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.05 (1 H, s), 1.34-1.49 (2 H, m), 1.95-2.02 (2 H, m), 2.47 (3 H, s), 2.55-2. 67 (1H, m), 2.90-3.01 (2H, m), 3.76-3.84 (2H, m), 6.82-6.90 (2H, m), 7.43- 7.50 (2H, m).

Reference Example 173
Preparation of N- (2-methyl-2-propenyl) carbamic acid benzyl ester 2-Methallylamine hydrochloride (21.52 g, 0.2 mol) is dissolved in water (200 ml) and benzyl chloroformate (37.53 g, 0 The mixture was ice cooled. Sodium carbonate (46.63 g, 0.44 mol) was added in small portions and stirred at room temperature for 3 hours. After extraction twice with methylene chloride, the organic phases were combined, dried over sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane / ethyl acetate = 7/1) to give N- (2-methyl-2-propenyl) carbamic acid benzyl ester (41.58 g, quantitative) as a colorless liquid The
¹ H-NMR (CDCl ₃ ) δ ppm:
1.74 (3 H, s), 3.75 (2 H, d, J = 6.2 Hz), 4.69-4.94 (2 H, m), 5.13 (2 H, s), 7. 26- 7.39 (5 H, m).

Reference Example 174
Preparation of N- (2-methyl-2-propenyl) carbamic acid 4-chlorobenzyl ester 4-chlorobenzyl alcohol (3.00 g, 21.0 mmol) and triphosgene (3.12 g, 10.5 mmol) in toluene The mixture was dissolved in 15 ml), N-ethyldiisopropylamine (3.6 ml, 21.0 mmol) was added under ice-cooling, and the mixture was stirred for 1 hour. Methylene chloride and water were added for extraction, and the organic phases were combined and dried over magnesium sulfate. Filter and concentrate the filtrate under reduced pressure. Water (40 ml) and 2-methallylamine hydrochloride (2.49 g, 23.1 mmol) were added to the obtained residue, sodium carbonate (5.15 g, 48.6 mmol) was added under ice-cooling, and the mixture was stirred for 15 minutes. Methylene chloride is added for extraction, the organic phases are combined, dried over magnesium sulfate and filtered, and the filtrate is concentrated under reduced pressure. The obtained residue is purified by silica gel column chromatography (n-hexane / ethyl acetate = 10/1) to give colorless liquid N- (2-methyl-2-propenyl) carbamic acid 4-chlorobenzyl ester (4.06 g) , Yield 80%).
¹ H-NMR (CDCl ₃ ) δ ppm:
1.74 (3 H, s), 3.74 (2 H, d, J = 5.8 Hz), 4.73-4.91 (2 H, m), 5.08 (2 H, s), 7.26 7.41 (4H, m).

Reference Example 175
Preparation of N- (2-methyl-2-propenyl) carbamic acid 4-fluorobenzyl ester 4-Fluorobenzyl alcohol (3.00 g, 23.8 mmol) was dissolved in THF (60 ml) '-Carbonyldiimidazole (4.05 g, 25.0 mmol) was added and stirred for 30 minutes. Add 2-methallylamine hydrochloride (2.81 g, 26.2 mmol) and triethylamine (3.98 g, 28.5 mmol), and stir for 2 hours under ice-cooling. After concentration under reduced pressure, extraction was performed by adding methylene chloride and water. The combined organic phases were dried over sodium sulfate and filtered. The filtrate is concentrated under reduced pressure and then purified by silica gel column chromatography (n-hexane / ethyl acetate = 10/1) to give N- (2-methyl-2-propenyl) carbamic acid 4-fluorobenzyl ester (4 of colorless liquid) .69 g (yield 88%) were obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.73 (3H, s), 3.74 (2H, d, J = 5.8 Hz), 4.55-4.95 (3H, m), 5.08 (2H, s), 6.95 7.14 (2H, m), 7.27-7.41 (2H, m).

Reference Example 176
Preparation of 3-methoxymethoxy-2-methyl-1-propene Chloromethyl methyl ether (105 ml) was stirred in a solution of 2-methyl-2-propen-1-ol (50 g, 693 mmol) in THF (500 ml) with ice cooling. 1386 mmol) and N-ethyldiisopropylamine (265 ml, 1525 mmol) were added and stirred at room temperature for 2 hours. The reaction mixture was filtered, washed with diethyl ether and the filtrate concentrated in vacuo. The residue is dissolved in diethyl ether, washed with water, saturated aqueous sodium hydrogen carbonate solution and water, dried over magnesium sulfate and concentrated under reduced pressure to give 3-methoxymethoxy-2-methyl-1-propene (9. 7 g, yield 12%) were obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.76 (3H, s), 3.39 (3H, s), 3.97 (2H, s), 4.65 (2H, s), 4.85-4.94 (1 H, m), 4 .98-5.06 (1 H, m).

Reference Example 177
Preparation of 2-methoxymethoxymethyl-2-methyloxirane m-chloroperbenzoic acid in a solution of 3-methoxymethoxy-2-methylpropene (9.7 g, 84 mmol) prepared in Reference Example 176 in methylene chloride (200 ml) (22.7 g, 92 mmol) was added little by little with ice-cooling and stirring for 6 hours at room temperature, sodium hydrogen carbonate (14.1 g, 168 mmol) and methylene chloride were added and stirred. The solution was separated, washed with aqueous sodium hydrogen carbonate solution, aqueous sodium thiosulfate solution, aqueous sodium hydrogen carbonate solution, dried over magnesium sulfate and concentrated under reduced pressure to give 2-methoxymethoxymethyl-2-methyloxirane (6.8 g) as a green liquid. , Yield 62%).
¹ H-NMR (CDCl ₃ ) δ ppm:
1.40 (3 H, s), 2.65 (1 H, d, J = 4.9 Hz), 2.78 (1 H, d, J = 4.9 Hz), 3.38 (3 H, s), 53 (1 H, d, J = 11.1 Hz), 3.62 (1 H, d, J = 11.1 Hz), 4.65 (2 H, s).

Reference Example 178
Preparation of 4- (4-chlorobenzyl) piperazine-1-carboxylic acid tert-butyl ester Potassium carbonate in a solution of piperazine-1-carboxylic acid tert-butyl ester (1.5 g, 8.05 mmol) in DMF (10 ml) (1.45 g, 10.47 mmol) and 4-chlorobenzyl chloride (1.82 g, 8.86 mmol) were added and stirred at 50 ° C. for 1 hour. It was diluted with ethyl acetate, washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride / ethyl acetate = 9/1) to give 4- (4-chlorobenzyl) piperazine-1-carboxylic acid tert-butyl ester (2.50 g, quantitative) as a colorless liquid I got
¹ H-NMR (CDCl ₃ ) δ ppm:
1.45 (9 H, s), 2.36 (4 H, t, J = 5.0 Hz), 3.42 (4 H, t, J = 5.0 Hz), 3.46 (2 H, s), 7. 23-7. 31 (4H, m).

Reference Example 179
Preparation of 1- (4-chlorobenzyl) piperazine Methylene chloride (16 ml) of 4- (4-chlorobenzyl) piperazine-1-carboxylic acid tert-butyl ester (2.50 g, 8.05 mmol) prepared in Reference Example 178 Trifluoroacetic acid (8 ml) was added to the solution and stirred at room temperature for 5 hours. The reaction solution was concentrated under reduced pressure. To the residue was added aqueous caustic soda, extracted with methylene chloride, dried over sodium sulfate and filtered. The filtrate was concentrated to give colorless liquid 1- (4-chlorobenzyl) piperazine (1.70 g, quantitative).
¹ H-NMR (DMSO-d ₆ ) δ ppm:
2.55 to 2.74 (4H, m), 3.57 to 3.76 (6H, m), 7.35 to 7.45 (4H, m), 8.55 to 8.88 (1H, br) ).

Reference Example 180
Preparation of 1- (4-trifluoromethylbenzyl) piperazine In the same manner as in Reference Example 179 using 4- (4-trifluoromethylbenzyl) piperazine-1-carboxylic acid tert-butyl ester, 1- (4-trimethyl) Fluoromethylbenzyl) piperazine was prepared.
100% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
2.72 (4H, t, J = 4.9 Hz), 3.16-3.26 (4 H, m), 3.62 (2 H, s), 7.44 (2 H, d, J = 8.1 Hz ), 7.59 (2H, d, J = 8.1 Hz).

Reference Example 181
Preparation of 1- (4-trifluoromethoxybenzyl) piperazine In the same manner as in Reference Example 179 using 4- (4-trifluoromethoxybenzyl) piperazine-1-carboxylic acid tert-butyl ester, Fluoromethoxybenzyl) piperazine was prepared.
100% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
2.70 (4H, t, J = 4.9 Hz), 3.19 (4 H, t, J = 4.9 Hz), 3.56 (2 H, s), 7.17 (2 H, d, J = 7) .9 Hz), 7.33 (2 H, d, J = 7.9 Hz).

Reference Example 182
Preparation of 4- [4- (4-trifluoromethoxybenzyl) piperazin-1-yl] phenol 4- (4-hydroxyphenyl) piperazine (3 g, 16.8 mmol) and 4-trifluoromethoxybenzaldehyde (3.36 g) , 17.7 mmol) was dissolved in methanol (60 ml) and methylene chloride (15 ml). To this solution was added under ice-cooling sodium cyanoborohydride (1.59 g, 25.3 mmol) and acetic acid (1.6 ml), and the mixture was warmed to room temperature and stirred for 2 hours. Saturated aqueous sodium hydrogen carbonate solution and methylene chloride were added, stirred and extracted with methylene chloride. The organic phase was washed with brine, dried over magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (methylene chloride / methanol = 100/1) to give 4- [4- (4-trifluoromethoxybenzyl) piperazin-1-yl] phenol (3.36 g) as white powder crystals. A yield of 57% was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
5.59-2.64 (4H, m), 3.05-3. 10 (4H, m), 3.56 (2H, s), 4.90-5. 40 (1 H, br), 6. 69-6.75 (2H, m), 6.79-6.85 (2H, m), 7.16 (2H, d, J = 8.4 Hz), 7.37 (2H, d, J = 8 .4 Hz).

Reference Example 183
Preparation of 1- [4- (Tetrahydropyran-2-yloxy) phenyl] -4- (4-trifluoromethoxyphenyl) piperazine 1- (4-Trifluoromethoxyphenyl) piperazine (4.4 g, 17.8 mmol) 2- (4-bromophenoxy) tetrahydropyran (4.6 g, 17.8 mmol), palladium acetate (159 mg, 0.71 mmol), BINAP (666 mg, 1.07 mmol) and tert-butoxy sodium (2. 2 g, 23.1 mmol) were heated to reflux for 5 hours in toluene (40 ml) under a nitrogen atmosphere. Ethyl acetate and water were added to the reaction solution, the mixture was stirred and the precipitate was removed by celite filtration, and the filtrate was extracted with ethyl acetate. The organic phase was washed with brine, dried over magnesium sulfate and filtered. The obtained filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (n-hexane / ethyl acetate = 20/1) to give 1- [4- (tetrahydropyran-2-yloxy) phenyl]-as a white powder. 4- (4-Trifluoromethoxyphenyl) piperazine (2.7 g, 35% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.54-2.05 (6H, m), 3.21-3.34 (8H, m), 3.55-3.64 (1H, m), 3.89-3.99 (1H, m) ), 5.31-5.34 (1H, m), 6.90-7.03 (6H, m), 7.11-7.16 (2H, m).

  This compound was also produced by the method of Reference Example 185.

Reference Example 184
Preparation of 1- [4- (tetrahydropyran-2-yloxy) phenyl] piperazine 2- (4-bromophenoxy) tetrahydropyran (7.8 g, 30.3 mmol), piperazine (15.7 g, 180 mmol), acetic acid Palladium (136 mg, 0.61 mmol), BINAP (567 mg, 0.91 mmol) and sodium tert-butoxy (3.8 g, 39.4 mmol) were heated to reflux under nitrogen atmosphere in toluene (50 ml) for 2 hours . Ethyl acetate and water were added to the reaction solution, the mixture was stirred and the precipitate was removed by celite filtration, and the filtrate was extracted with ethyl acetate. The organic phase was washed with brine, dried over magnesium sulfate and filtered. The obtained filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (n-hexane / ethyl acetate = 20/1) to obtain 1- [4- (tetrahydropyran-2-yloxy) phenyl] of light gray powder. The piperazine (6.8 g, 85% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.57-2.04 (6H, m), 3.00-3.06 (8H, m), 3.53-3.66 (1H, m), 3.89-3.99 (1H, m) ), 5.29-5.32 (1 H, m), 6.84-6. 90 (2 H, m), 6.95-7.02 (2 H, m).

Reference Example 185
Preparation of 1- [4- (tetrahydropyran-2-yloxy) phenyl] -4- (4-trifluoromethoxyphenyl) piperazine (another synthetic method of the compound of Reference Example 183)
1- [4- (tetrahydropyran-2-yloxy) phenyl] piperazine (2.1 g, 8.05 mmol) prepared in Reference Example 184, 4-trifluoromethoxy-1-bromobenzene (1.9 g, 8. 05 mmol), palladium acetate (72 mg, 0.32 mmol), BINAP (300 mg, 0.48 mmol) and sodium tert-butoxy (1.0 g, 10.5 mmol) in toluene (30 ml) under a nitrogen atmosphere. Heated to reflux for 5 hours. Ethyl acetate and water were added to the reaction solution, the mixture was stirred and the precipitate was removed by celite filtration, and the filtrate was extracted with ethyl acetate. The organic phase was washed with brine, dried over magnesium sulfate and filtered. The obtained filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (n-hexane / ethyl acetate = 20/1) to give 1- [4- (tetrahydropyran-2-yloxy) phenyl]-as a white powder. 4- (4-Trifluoromethoxyphenyl) piperazine (3.1 g, 90% yield) was obtained.

Reference Example 186
Preparation of 4- [4- (4-trifluoromethoxyphenyl) piperazin-1-yl] phenol 1- [4- (tetrahydropyran-2-yloxy) phenyl] -4- (4-tri) prepared in Reference Example 185 Fluoromethoxyphenyl) piperazine (2.65 g, 6.27 mmol) was suspended in ethanol (50 ml), pyridinium p-toluenesulfonate (473 mg, 1.88 mmol) was added and stirred at 70 ° C. for 5 hours. Ethanol was distilled off under reduced pressure, and methylene chloride and a saturated aqueous solution of sodium hydrogen carbonate were added to the residue and stirred. This was extracted with methylene chloride, dried over magnesium sulfate and filtered. The obtained filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 10/1) to obtain 4- [4- (4-trifluoromethoxyphenyl) piperazine-1-white powder. [I] phenol (1.95 g, 92% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
3.19-3.24 (4H, m), 3.29-3.34 (4H, m), 4.50 (1H, s), 6.76-6.80 (2H, m), 6. 87-6.97 (4H, m), 7.11-7.15 (2H, m).

  The compounds of Reference Example 187 and Reference Example 188 were produced in the same manner as in Reference Example 186, using the corresponding starting materials.

Reference Example 187
4- [4- (4-Trifluoromethylphenyl) piperazin-1-yl] phenol white powder, yield 82%
¹ H-NMR (CDCl ₃ ) δ ppm:
3.18-3.23 (4H, m), 3.41-3. 45 (4H, m), 4.47 (1H, s), 6.76-6.82 (2H, m), 6. 87-7.00 (4H, m), 7.48-7.52 (2H, m).

Reference Example 188
4- [4- (4-Chlorophenyl) piperazin-1-yl] phenol white powder, yield 23%
¹ H-NMR (CDCl ₃ ) δ ppm:
3.18-3.23 (4H, m), 3.28-3. 32 (4H, m), 4.45 (1 H, s), 6.77-6. 81 (2 H, m), 6. 87-6, 92 (4H, m), 7.21-7.24 (2H, m).

Reference Example 189
Preparation of 4- (4-trifluoromethoxyphenoxy) piperidine-1-carboxylic acid tert-butyl ester 4-hydroxypiperidine-1-carboxylic acid tert-butyl ester (56.5 g, 0.28 mol), 4-trifluoro Methoxyphenol (50 g, 0.28 mol) and triphenylphosphine (108 g, 0.42 mol) were dissolved in THF (500 ml). Under heating to reflux, diethyl azodicarboxylate (65 ml, 0.42 mol) was added dropwise, and the mixture was stirred for 5 hours. The reaction mixture is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (n-hexane / ethyl acetate = 5/1) to give 4- (4-trifluoromethoxyphenoxy) piperidine-1-carboxylic acid tert- of a colorless oil. The butyl ester (92 g, 91% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.47 (9H, s), 1.69-1.80 (2H, m), 1.85 to 1.96 (2H, m), 3.28-3. 39 (2H, m), 3. 64-3.75 (2H, m), 4.40-4. 46 (1H, m), 6.85-6.92 (2H, m), 7.11-7.15 (2H, m).

Reference Example 190
Preparation of 4- (4-trifluoromethoxyphenoxy) piperidine 4- (4-Trifluoromethoxyphenoxy) piperidine-1-carboxylic acid tert-butyl ester (92 g, 254.59 mmol) prepared in Reference Example 189 with methylene chloride It was dissolved in (100 ml). Under room temperature, trifluoroacetic acid (200 ml) was added dropwise and stirred overnight. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in methylene chloride again. The solution was made alkaline with aqueous sodium hydroxide solution and extracted with methylene chloride. The organic phase was washed with brine, dried over sodium sulfate and filtered. The obtained filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (methylene chloride / methanol = 5/1) to give 4- (4-trifluoromethoxyphenoxy) piperidine (55 g, yield 83%) as a white powder. Got).
¹ H-NMR (CDCl ₃ ) δ ppm:
1.65-1.78 (2H, m), 2.00-2.07 (2H, m), 2.73-2.83 (2H, m), 3.12-3.21 (2H, m) ], 4.32-4.38 (2H, m), 6.85-6.92 (2H, m), 7.10-7.15 (2H, m).

Reference Example 191
Preparation of 1- [4- (tetrahydropyran-2-yloxy) phenyl] -4- (4-trifluoromethoxyphenoxy) piperidine 4- (4-trifluoromethoxyphenoxy) piperidine prepared in Reference Example 190 (30.3 g) 0.116 mol), 2- (4-bromophenoxy) tetrahydropyran (30 g, 0.116 mol), palladium acetate (1.0 g, 4.64 mmol), BINAP (4.3 g, 6.96 mmol) And cesium carbonate (49 g, 0.151 mol) were heated under reflux in toluene (300 ml) under a nitrogen atmosphere for 30 hours. Ethyl acetate and water were added to the reaction solution, the mixture was stirred and the precipitate was removed by celite filtration, and the filtrate was extracted with ethyl acetate. The organic phase was washed with brine, dried over magnesium sulfate and filtered. The obtained filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (n-hexane / ethyl acetate = 20/1) to give 1- [4- (tetrahydropyran-2-yloxy) phenyl]-of yellow powder. 4- (4-Trifluoromethoxyphenoxy) piperidine (32.6 g, yield 64%) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.55-1.75 (3H, m), 1.81-2.20 (7H, m), 2.95-3.04 (2H, m), 3.38-3. 42 (2H, m) ), 3.55 to 3.66 (1H, m), 3.87 to 3.99 (1H, m), 4.36 to 4.45 (1H, m), 5.29 to 5.32 (1H) , M), 6.89-7.01 (6 H, m), 7.1 1-7. 16 (2 H, m).

Reference Example 192
Preparation of 4- [4- (4-trifluoromethoxyphenoxy) piperidin-1-yl] phenol 1- [4- (tetrahydropyran-2-yloxy) phenyl] -4- (4-tri) prepared in Reference Example 191 Fluoromethoxyphenoxy) piperidine (30.1 g, 68.8 mmol) is suspended in ethanol (450 ml), pyridinium p-toluenesulfonate (5.2 g, 20.6 mmol) is added, and it is kept at 70 ° C. for 24 hours It stirred. Ethanol was distilled off under reduced pressure, and methylene chloride and saturated aqueous sodium hydrogen carbonate solution were added to the residue and stirred. This was extracted with methylene chloride, dried over magnesium sulfate and filtered. The obtained filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 10/1) to obtain light brown powder of 4- [4- (4-trifluoromethoxyphenoxy) piperidine-1 Y-yl] phenol (22.9 g, 94% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.88-2.02 (2H, m), 2.06-2.16 (2H, m), 2.92-3.02 (2H, m), 3.30-3. 39 (2H, m) ), 4.36-4.44 (1H, m), 4.74 (1H, s), 6.71-6.78 (2H, m), 6.85-6.94 (4H, m), 7.10-7.16 (2H, m).

Reference Example 193
Preparation of 4- [2-Chloro-4- (tetrahydropyran-2-yloxy) phenyl] piperazine-1-carboxylic acid tert-butyl ester Piperazine-1-carboxylic acid tert-butyl ester (3.94 g, 21.6 mmol ), 2- (4-bromo-3-chlorophenoxy) tetrahydropyran (5.61 g, 19.2 mol), palladium acetate (86.4 mg, 0.39 mmol), BINAP (172 mg, 0.58 mmol) and Sodium tert-butoxy (2.4 g, 25.0 mmol) was heated to reflux under toluene atmosphere in toluene (40 ml) for 2 hours. Ethyl acetate and water were added to the reaction solution, the mixture was stirred and the precipitate was removed by celite filtration, and the filtrate was extracted with ethyl acetate. The organic phase was washed with brine, dried over magnesium sulfate and filtered. The obtained filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (n-hexane / ethyl acetate = 20/1) to give 4- [2-chloro-4- (tetrahydropyran-2-yl) as a yellow oily substance. Iryloxy) phenyl] piperazine-1-carboxylic acid tert-butyl ester (4.72 g, 62% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.48 (9 H, s), 1.51 to 2.04 (6 H, m), 2.88 to 2.93 (4 H, m), 3.56 to 3.63 (5 H, m), 83-3.94 (1 H, m), 5.31-5. 34 (1 H, m), 6.88-6. 96 (2 H, m), 7. 10-7. 13 (1 H, m).

Reference Example 194
Preparation of 4- (2-chloro-4-hydroxyphenyl) piperazine-1-carboxylic acid tert-butyl ester 4- [2-chloro-4- (tetrahydropyran-2-yloxy) phenyl] piperazine prepared in Reference Example 193 A 1-carboxylic acid tert-butyl ester (4.73 g, 11.9 mmol) was suspended in ethanol (50 ml), a catalytic amount of pyridinium p-toluenesulfonate was added, and the mixture was stirred at 70 ° C. for 1 hour. Ethanol was distilled off under reduced pressure, and methylene chloride and saturated aqueous sodium hydrogen carbonate solution were added to the residue and stirred. The precipitate was collected by filtration and then dried under reduced pressure to obtain 4- (2-chloro-4-hydroxyphenyl) piperazine-1-carboxylic acid tert-butyl ester (2.68 g, yield 72%) as a white powder.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.49 (9 H, s), 2.87-2.91 (4 H, m), 3.55-3. 60 (4 H, m), 5.19 (1 H, br), 6.68-6. 74 (1 H, m), 6.88-6. 93 (2 H, m).

Reference Example 195
Preparation of 4- (4-Acetoxybenzoyl) piperazine-1-carboxylic acid tert-butyl ester p-Acetoxybenzoic acid (11 g, 61.1 mmol) is dissolved in methylene chloride (100 ml), DMF (3 drops) and chloride Thionyl (5.54 ml, 76.3 mmol) was added and the mixture was heated to reflux for 2 hours. This is ice-cooled, and a solution of piperazine-1-carboxylic acid tert-butyl ester (10.3 g, 55.5 mmol) and pyridine (12 ml, 0.15 mol) in methylene chloride (100 ml) is added dropwise, and 2 hours Stir at room temperature. The reaction mixture was diluted with methylene chloride, washed with water, 10% hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (methylene chloride / ethyl acetate = 20/1) to give 4- (4-acetoxybenzoyl) piperazine-1-carboxylic acid tert-butyl ester (18.5 g, yield) as a white solid. 87%).
¹ H-NMR (CDCl ₃ ) δ ppm:
1.47 (9H, s), 2.31 (3H, s), 3.46 (8H, br), 7.12-7.18 (2H, m), 7.41-7.46 (2H, 2) m).

Reference Example 196
Preparation of 4- (4-hydroxybenzoyl) piperazine-1-carboxylic acid tert-butyl ester 4- (4-acetoxybenzoyl) piperazine-1-carboxylic acid tert-butyl ester prepared in Reference Example 195 (18.5 g, 53) 1 mmol) was dissolved in methanol (200 ml), potassium carbonate (370 mg, 2.65 mmol) was added and stirred overnight at room temperature. The reaction solution was concentrated under reduced pressure, 5% hydrochloric acid and methylene chloride were added to the residue, and the mixture was vigorously stirred. The precipitate is collected by filtration, washed with water and methylene chloride and dried under reduced pressure to give 4- (4-hydroxybenzoyl) piperazine-1-carboxylic acid tert-butyl ester (14.9 g, yield 92%) as a white powder. Got).
¹ H-NMR (CDCl ₃ ) δ ppm:
1.48 (9H, s), 3.46 (4H, br), 3.60 (4H, br), 6.75-6.79 (2H, m), 7.22-7.28 (2H, 2H, s) m).

Reference Example 197
Preparation of 1-benzyl-4- [4- (tetrahydropyran-2-yloxy) phenyl] piperidin-4-ol 2- (4-bromophenoxy) tetrahydropyran (7.2 g, 28 mmol) in THF (70 ml) Melted and cooled to -60 ° C. n-Butyllithium (1.53 M) hexane solution (20 ml, 30.8 mmol) was added dropwise and stirred for 30 minutes. A solution of 1-benzyl-4-piperidone (5.3 g, 28 mmol) in THF (20 ml) was added dropwise and stirred for 3 hours while warming up to 0 ° C. Aqueous ammonium chloride solution was added to the reaction solution, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue is separated and purified by silica gel column chromatography (n-hexane / ethyl acetate = 20/1) to obtain 1-benzyl-4- [4- (tetrahydropyran-2-yloxy) phenyl] piperidine-4- orange oil. All (5.27 g, 51% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.52-2.21 (11 H, m), 2.41-2.52 (2 H, m), 2.75-2.82 (2 H, m), 3.57 (2 H, s), 3. 56-3.63 (1H, m), 3.83-3.96 (1H, m), 5.39-5. 42 (1H, m), 6.98-7.04 (2H, m), 7.20-7.44 (7H, m).

Reference Example 198
Preparation of 4- (4-hydroxyphenyl) piperidine-1-carboxylic acid tert-butyl ester 1-benzyl-4- [4- (tetrahydropyran-2-yloxy) phenyl] piperidin-4-ol prepared in Reference Example 197 (1.67 g, 4.55 mmol) was dissolved in acetonitrile (45 ml) and cooled to -10.degree. Triethylsilane (2.9 ml, 18.2 mmol) and boron trifluoride diethyl etherate (1.1 ml, 9.1 mmol) were added to the cooling liquid and stirred at room temperature for 2 days. Water was added to the reaction solution and extracted with methylene chloride. After drying over magnesium sulfate and filtration, the obtained filtrate was concentrated under reduced pressure. The residue was dissolved in ethanol (50 ml), a catalytic amount of 20% palladium hydroxide / carbon was added, and stirred overnight at room temperature under a hydrogen atmosphere. The reaction solution was filtered through celite, di-tert-butyl dicarbonate (1.1 ml, 4.78 mmol) was added to the filtrate, and the mixture was stirred at room temperature for 30 minutes. The reaction solution is concentrated under reduced pressure, and the residue is separated and purified by silica gel column chromatography (methylene chloride / methanol = 50/1) to obtain 4- (4-hydroxyphenyl) piperidine-1-carboxylic acid tert-butyl ester as a white solid. (1.07 g, 85% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.41-1.63 (2H, m), 1.49 (9H, s), 1.73-1.80 (2H, m), 2.50-2.62 (1 H, m), 73-2.83 (2H, m), 4.19-4.24 (2H, m), 5.87 (1H, bs), 6.76-6.81 (2H, m), 7.02- 7.08 (2H, m).

Reference Example 199
Preparation of 4- [3- (tetrahydropyran-2-yloxy) phenyl] piperazine-1-carboxylic acid tert-butyl ester Piperazine-1-carboxylic acid tert-butyl ester (2.94 g, 15.8 mmol), 2- (3-Bromophenoxy) tetrahydropyran (3.69 g, 14.4 mmol), palladium acetate (64 mg, 0.29 mmol), BINAP (285 mg, 0.43 mmol) and tert-butoxy sodium (1.8 g, 18 .7 mmol) was heated to reflux for 2 hours in toluene (40 ml) under a nitrogen atmosphere. Ethyl acetate and water were added to the reaction solution, the mixture was stirred and the precipitate was removed by celite filtration, and the filtrate was extracted with ethyl acetate. The organic phase was washed with brine, dried over magnesium sulfate and filtered. The obtained filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (n-hexane / ethyl acetate = 20/1) to give 4- [3- (tetrahydropyran-2-yloxy) phenyl] as a colorless oil. Piperazine-1-carboxylic acid tert-butyl ester (5.3 g, yield 99%) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.48 (9 H, s), 1.52-2.04 (6 H, m), 3.10-3.15 (4 H, m), 3.53-3.64 (5 H, m), 87-3.94 (1 H, m), 5. 38-5. 41 (1 H, m), 6.5 3-6. 63 (3 H, m), 7.1 2-7. 19 (1 H, m).

Reference Example 200
Preparation of 4- (3-hydroxyphenyl) piperazine-1-carboxylic acid tert-butyl ester tert-butyl 4- [3- (tetrahydropyran-2-yloxy) phenyl] piperazine-1-carboxylic acid prepared in Reference Example 199 The ester (5.20 g, 14.4 mmol) was suspended in ethanol (100 ml), a catalytic amount of pyridinium p-toluenesulfonate was added, and the mixture was stirred at 70 ° C. for 1.5 hours. Ethanol was distilled off under reduced pressure, and methylene chloride and saturated aqueous sodium hydrogen carbonate solution were added to the residue and stirred. The precipitate was collected by filtration and then dried under reduced pressure to give 4- (3-hydroxyphenyl) piperazine-1-carboxylic acid tert-butyl ester (3.73 g, yield 93%) as a pale brown powder.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.49 (9 H, s), 3.09-3.14 (4 H, m), 3.54-3.59 (4 H, m), 5. 38 (1 H, br), 6.33-6. 41 (2H, m), 6.47-6.52 (1 H, m), 7.08-7.15 (1 H, m).

Reference Example 201
Preparation of 3-methyl-2-methylenebutyraldehyde Journal of American Chemical Society, 1957 p. 3-Methyl-2-methylenebutyraldehyde was prepared according to the method described in 3267 (J. Am. Chem. Soc., 3267, 1957). Thus, isovaleraldehyde (100 ml, 932 mmol), 37% formalin (83.8 ml, 1120 mmol) and dimethylamine hydrochloride (91.2 g, 1120 mmol) were stirred at 70 ° C. for 30 hours. Steam distillation, the fractions were separated and the aqueous phase was extracted with diethyl ether. The organic phases were combined, dried over sodium sulfate and concentrated under reduced pressure. The concentrate was distilled to obtain colorless liquid 3-methyl-2-methylenebutyraldehyde (65.5 g, yield 72%).
Boiling point 105-115 ° C
¹ H-NMR (CDCl ₃ ) δ ppm:
1.08 (6H, d, J = 6.9 Hz), 2.75-2.89 (1 H, m), 5.95 (1 H, s), 6.24 (1 H, s), 9.53 ( 1 H, s).

Reference Example 202
Preparation of 3-Methyl-2-methylenebutan-1-ol A solution of 3-methyl-2-methylenebutyraldehyde (65 g, 668 mmol) prepared in Reference Example 201 in THF (30 ml) was treated with lithium aluminum hydride (14. A suspension of 15 g (373 mmol) in THF (1000 ml) was added dropwise with ice-cooling and stirring, and further allowed to warm up naturally and stirred for 2 hours. Under ice-cooling, water, a 15% aqueous solution of sodium hydroxide and water are added, and the mixture is filtered, dried over sodium sulfate, concentrated under reduced pressure, and colorless liquid 3-methyl-2-methylenebutan-1-ol (61.5 g, Yield 93%).
¹ H-NMR (CDCl ₃ ) δ ppm:
1.07 (6 H, d, J = 6.9 Hz), 1.42 (1 H, t, J = 6.1 Hz), 2.25 to 2.43 (1 H, m), 4.13 (2 H, d , J = 6.1 Hz), 4.84-4.93 (1 H, m), 4.98-5.05 (1 H, m).

Reference Example 203
Preparation of 2-methoxymethoxymethyl-3-methyl-1-butene Ice-cold solution of 3-methyl-2-methylenebutan-1-ol (61.5 g, 615 mmol) prepared in Reference Example 202 in THF (500 ml) Under stirring, chloromethyl methyl ether (98 ml, 1292 mmol) and N-ethyldiisopropylamine (234 ml, 1344 mmol) were added and stirred at room temperature for 22 hours. The reaction solution was filtered and the filtrate was concentrated under reduced pressure. Diethyl ether was added, and the mixture was washed with water and saturated brine, dried over sodium sulfate and concentrated under reduced pressure to give 2-methoxymethoxymethyl-3-methyl-1-butene (89 g, quantitative) as a colorless liquid.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.07 (6H, d, J = 6.9 Hz), 2.25-2.41 (1H, m), 3.39 (3H, s), 4.05 (2H, s), 4.65 ( 2H, s), 4.87-4.95 (1 H, m), 5.00-5. 05 (1 H, m).

Reference Example 204
Preparation of 2-methylenebutyraldehyde A mixture of butyraldehyde (100 ml, 1110 mmol), 37% formalin (99.8 ml, 1330 mmol) and dimethylamine hydrochloride (108.6 g, 1330 mmol) was stirred at 70 ° C. for 23 hours . Steam distillation, the fractions were separated and the aqueous phase was extracted with diethyl ether. The organic phases were combined, dried over sodium sulfate and concentrated under reduced pressure. The concentrate was distilled to obtain colorless liquid 2-methylenebutyraldehyde (66.9 g, yield 72%).
Boiling point 70-93 ° C
¹ H-NMR (CDCl ₃ ) δ ppm:
1.08 (3 H, t, J = 7.5 Hz), 2.27 (2 H, q, J = 7.5 Hz), 5.98 (1 H, s), 6.25 (1 H, s), 9. 56 (1 H, s).

Reference Example 205
Preparation of 2-Methylene-1-Butanol A suspension of 2-methylenebutyraldehyde (66.9 g, 796 mmol) prepared in Reference Example 204 in lithium aluminum hydride (15.1 g, 398 mmol) in THF (1000 ml) The mixture was added dropwise with ice-cooling and stirring, and stirred at the same temperature for 1 hour. Water, a 15% aqueous solution of sodium hydroxide and water were added, filtered, dried over sodium sulfate and concentrated under reduced pressure to obtain 2-methylene-1-butanol (65.1 g, yield 95%) as a colorless liquid.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.07 (3 H, t, J = 7.5 Hz), 1. 44 (1 H, t, J = 6.0 Hz), 2. 13 (2 H, q, J = 7.5 Hz), 4.09 (2 H , D, J = 6.0 Hz), 4.82-4.93 (1 H, m), 4.98-5.07 (1 H, m).

Reference Example 206
Preparation of 2-methoxymethoxymethyl-1-butene Chloromethyl methyl ether (103) was stirred in a solution of 2-methylene-1-butanol (65.1 g, 757 mmol) prepared in Reference Example 205 in THF (750 ml) under ice-cooling and stirring. .4 ml, 1363 mmol) and N-ethyldiisopropylamine (247.2 ml, 1419 mmol) were added and stirred at room temperature for 3 days. The reaction mixture was filtered and the filtrate concentrated in vacuo. The residue was dissolved in diethyl ether, washed with water and saturated brine, dried over sodium sulfate and concentrated under reduced pressure to give 2-methoxymethoxymethyl-1-butene (98 g, quantitative) as a colorless liquid.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.07 (3 H, t, J = 7.5 Hz), 2.09 (2 H, q, J = 7.5 Hz), 3.38 (3 H, s), 4.01 (2 H, s), 4. 64 (2H, s), 4.86-4.95 (1 H, m), 5.00-5. 05 (1 H, m).

Reference Example 207
Preparation of 4- [2-Oxo-2- (4-oxopiperidin-1-yl) ethyl] piperazine-1-carboxylic acid tert-butyl ester 1- (2-chloroacetyl) piperidin-4-one (5.17 g , 29.4 mmol) was dissolved in acetonitrile (50 ml). To this solution was added piperazine-1-carboxylic acid tert-butyl ester (5.48 g, 29.4 mmol) and N-ethyldiisopropylamine (6.2 ml, 35.3 mmol) and heated to reflux for 2 hours. The reaction solution is cooled to room temperature, water is added, and the mixture is extracted with ethyl acetate. The organic phase was washed with brine, dried over magnesium sulfate and filtered. The obtained filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (methylene chloride / methanol = 100/1) to give 4- [2-oxo-2- (4-oxopiperidine) as a pale yellow solid -1-yl) ethyl] piperazine-1-carboxylic acid tert-butyl ester (6.49 g, 68% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.46 (9H, s), 2.44-2.54 (8H, m), 3.28 (2H, s), 3.42-3.47 (4H, m), 3.85-3. 90 (4H, m).

Reference Example 208
Preparation of acetic acid 4-methyl-4-pentenyl ester To a mixture of methyltriphenylphosphonium bromide (30 g, 84 mmol) and THF (300 ml) was added potassium tert-butoxide (9.4 g, 84 mmol), and the solution was stirred at room temperature 40 Stirred for a minute. Under ice-cooling, a solution of acetic acid 4-oxopentyl ester (9.9 g, 68.8 mmol) dissolved in THF (30 ml) was gradually added dropwise, and stirred at room temperature for 2 hours. The reaction solution was poured into ice water and extracted twice with diethyl ether. The organic phases were combined, washed with brine and dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane / ethyl acetate = 4/1) to obtain acetic acid 4-methyl-4-pentenyl ester (5.9 g, yield 60.4%) as a colorless oil.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.70-1.86 (5 H, m), 2.00-2. 14 (5 H, m), 4.07 (2 H, t, J = 6.7 Hz), 4.69 (1 H, s), 4.74 (1 H, s).

Reference Example 209
Preparation of 4- (2-methyl-2-oxiranylmethyl) piperazine-1-carboxylic acid benzyl ester With a suspension of sodium hydride (0.37 g, 9.32 mmol) in DMSO (20 ml) under ice cooling Trimethylsulfoxonium iodide (1.96 g, 8.91 mmol) was added, and the mixture was stirred at room temperature for 30 minutes to give 4- (2-oxopropyl) piperazine-1-carboxylic acid benzyl ester (2.24 g, 8). A solution of .10 mmol) in DMSO (10 ml) was added and further stirred at room temperature for 1 hour. The mixture was poured into ice water, extracted with diethyl ether, washed with water, dried over magnesium sulfate and concentrated under reduced pressure. A slightly yellow liquid 4- (2-methyl-2-oxiranylmethyl) piperazine-1-carboxylic acid benzyl ester (1.51 g, yield 64%) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.37 (3H, s), 2.27-2.63 (8H, m), 3.44-3.63 (4H, m), 5.13 (2H, s), 7.29-7. 44 (5 H, m).

Reference Example 210
Preparation of 4- (2-methyl-2-oxiranylmethyl) homopiperazine-1-carboxylic acid tert-butyl ester Sodium hydride (4.3 g, 109 mmol) was suspended in DMSO (200 ml), trimethylsulfoxo was used. Add slowly sodium iodide (22.95 g, 104 mmol) and stir at room temperature for 2 hours. A solution of 4- (2-oxopropyl) homopiperazine-1-carboxylic acid tert-butyl ester (24.3 g, 94.8 mmol) prepared in Reference Example 10 in DMSO (25 ml) was added to the resulting mixture. The solution was gradually added dropwise and stirred at room temperature for 1 hour. The reaction solution was poured into ice water, extracted with diethyl ether, and dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / methanol = 100/1) to give 4- (2-methyl-2-oxiranylmethyl) homopiperazine-1-carboxylic acid tert-butyl ester of a slightly yellow oil ( 15.38 g (yield 60%) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.38 (3 H, s), 1.43 (9 H, s), 1.69-1.90 (2 H, m), 2.40-2.75 (8 H, m), 3.36-3. 55 (4H, m).

Reference Example 211
Preparation of 4- [2- (2-Methyl-2-oxiranyl) ethyl] piperazine-1-carboxylic acid tert-butyl ester Sodium hydride (1.2 g, 35 mmol) was suspended in DMSO (120 ml) under nitrogen atmosphere. The solution became cloudy, trimethylsulfoxonium iodide (7.8 g, 35 mmol) was gradually added, and the mixture was stirred at room temperature for 2 hours. To the resulting mixture was slowly added dropwise a solution of 4- (3-oxobutyl) piperazine-1-carboxylic acid tert-butyl ester (6.1 g, 23.8 mmol) in DMSO (10 ml) at room temperature. The mixture was stirred for 1.5 hours and then at 50 to 60 ° C. for 1.5 hours. The reaction solution was cooled to room temperature, poured into ice water, and extracted three times with ethyl acetate. The organic phases were combined, washed three times with water, then washed with saturated brine and dried over sodium sulfate. After filtration, the filtrate is concentrated under reduced pressure, and 4- [2- (2-methyl-2-oxiranyl) ethyl] piperazine-1-carboxylic acid tert-butyl ester (5.6 g, yield 87) as a slightly yellow oil. %) Got.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.33 (3 H, s), 1.46 (9 H, s), 1.66-1.85 (2 H, m), 2.28-2.50 (6 H, m), 2.55-2. 66 (2H, m), 3.33-3.47 (4H, m).

Reference Example 212
Preparation of 1- (2-methyl-2-oxiranylmethyl) -4- (4-trifluoromethylphenyl) piperazine Sodium hydride (484 mg, 12.1 mmol) was suspended in dimethyl sulfoxide (30 ml) . Trimethylsulfoxonium iodide (2.5 g, 11.6 mmol) was added little by little to this suspension and stirred at room temperature for 1 hour. A solution of 1- [4- (4-trifluoromethylphenyl) piperazin-1-yl] propan-2-one (3.4 g, 11.9 mmol) in dimethyl sulfoxide (20 ml) was added to the resulting mixture. Add and stir at room temperature for 1 hour. The reaction solution was poured into ice water and extracted with diethyl ether. The organic phase was washed with brine, dried over magnesium sulfate and filtered. The obtained filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (methylene chloride / methanol = 100/1) to obtain 1- (2-methyl-2-oxiranylmethyl) as a pale yellow powder. -4- (4-Trifluoromethylphenyl) piperazine (3.2 g, 98% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.40 (3 H, s), 2. 33 (1 H, d, J = 13.0 Hz), 2.53-2.73 (7 H, m), 3.26-3.30 (4 H, m), 6.91 (2H, d, J = 8.7 Hz), 7.47 (2 H, d, J = 8.7 Hz).

  The compounds of Reference Example 213 to Reference Example 217 were produced in the same manner as in Reference Example 212.

Reference Example 213
1- (2-Methyl-2-oxiranylmethyl) -4- (4-biphenylyl) piperazine pale yellow powder, yield 99%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.41 (3 H, s), 2.37 (1 H, d, J = 12.9 Hz), 2.58-2.76 (7 H, m), 3.23-3.28 (4 H, m), 6.97-7.01 (2H, m), 7.24-7.30 (1H, m), 7.37-7.43 (2H, m), 7.49-7.58 (4H, m) ).

Reference Example 214
1- (2-Methyl-2-oxiranylmethyl) -4- (4-chlorophenyl) piperazine pale yellow powder, yield 99%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.39 (3 H, s), 2. 34 (1 H, d, J = 12.9 Hz), 2.54-2.73 (7 H, m), 3.14-3.18 (4 H, m), 6.81-6.87 (2H, m), 7.16-7.22 (2H, m).

Reference Example 215
1- (2-Methyl-2-oxiranylmethyl) -4- (4-trifluoromethoxyphenyl) piperazine pale yellow powder, yield 99%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.40 (3 H, s), 2. 34 (1 H, d, J = 12.9 Hz), 2.54-2.73 (7 H, m), 3.16-3.20 (4 H, m), 6.85-6.92 (2H, m), 7.08-7. 13 (2H, m).

Reference Example 216
1- (2-Methyl-2-oxiranylmethyl) -4- (pyridin-2-yl) piperazine pale yellow powder, yield 99%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.41 (3 H, s), 2. 35 (1 H, d, J = 12.9 Hz), 2.50-2.69 (7 H, m), 3.48-3. 60 (4 H, m), 6.59-6.66 (2H, m), 7.43-7.50 (1H, m), 8.17-8.20 (1H, m).

Reference Example 217
1- (2-Methyl-2-oxiranylmethyl) -4- (pyrimidin-2-yl) piperazine pale yellow powder, yield 99%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.41 (3 H, s), 2.36 (1 H, d, J = 12.9 Hz), 2.45-2.64 (7 H, m), 3.81-3. 85 (4 H, m), 6.47 (1 H, t, J = 4.8 Hz), 8.30 (2 H, d, J = 4.8 Hz).

Reference Example 218
Preparation of N-methyl- [1- (2-methyl-2-oxiranylmethyl) piperidin-4-yl] carbamic acid tert-butyl ester Sodium hydride (372 mg, 9.32 mmol) in dimethyl sulfoxide (20 ml) Was suspended. Trimethylsulfoxonium iodide (1.96 g, 8.89 mmol) was added little by little to this suspension and stirred at room temperature for 1.5 hours. A solution of N-methyl- [1- (2-oxopropyl) piperidin-4-yl] carbamic acid tert-butyl ester (2.3 g, 8.5 mmol) dissolved in dimethyl sulfoxide (20 ml) in the resulting mixture Was added and stirred at room temperature for 2 hours. The reaction solution was poured into ice water and extracted with diethyl ether. The organic phase was washed with brine, dried over magnesium sulfate and filtered. The obtained filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (methylene chloride / methanol = 100/1) to give N-methyl- [1- (2-methyl-2) as a pale yellow oil. -Oxiranylmethyl) piperidin-4-yl] carbamic acid tert-butyl ester (2.1 g, yield 86%) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.36 (3H, s), 1.46 (9H, s), 1.55 to 1.79 (5H, m), 1.97-2.13 (2H, m), 2.30 (1H, 1H, s) d, J = 12.9 Hz), 2.49 (1 H, d, J = 12.9 Hz), 2.59 (2 H, s), 2.74 (3 H, s), 2.88-3. 2H, m).

Reference Example 219
Preparation of 3- (2-methyl-2-oxiranyl) pyridine In the same manner as in Reference Example 218 using 3-acetylpyridine (8 g, 66.1 mmol), a light tea oil 3- (2-methyl-2-) was prepared. Oxiranyl) pyridine (7 g, 78.4% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.74 (3 H, s), 2.82 (1 H, d, J = 5.2 Hz), 3.02 (1 H, d, J = 5.2 Hz), 7.21 to 7.33 (1 H, m) ), 7.58-7. 70 (1 H, m), 8.54 (1 H, dd, 1.6 Hz, 4.8 Hz), 8.65 (1 H, d, J = 2.3 Hz).

Reference Example 220
Preparation of 1-oxa-6-azaspiro [2,5] octane-6-carboxylic acid tert-butyl ester Sodium hydride (13.3 g, 0.33 mol) was suspended in dimethyl sulfoxide (600 ml). To this suspension, trimethylsulfoxonium iodide (70 g, 0.32 mol) was added little by little and stirred at room temperature for 1 hour. To the resulting mixture was slowly added 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (58 g, 0.291 mol) and stirred at 55 ° C. for 1 hour. The reaction solution was poured into ice water and extracted with diethyl ether. The organic phase was washed with brine, dried over magnesium sulfate and filtered. The obtained filtrate is concentrated under reduced pressure, and the residue is crystallized with n-hexane to give white powder of 1-oxa-6-azaspiro [2,5] octane-6-carboxylic acid tert-butyl ester (61.7 g) , Yield 96%).
¹ H-NMR (CDCl ₃ ) δ ppm:
1.40-1.53 (2H, m), 1.47 (9H, s), 1.72-1.85 (2H, m), 2.69 (2H, s), 3.37-3. 48 (2H, m), 3.67-3.77 (2H, m).

Reference Example 221
Preparation of 4- [2- (1-oxa-6-azaspiro [2,5] octan-6-yl) -2-oxoethyl] piperazine-1-carboxylic acid tert-butyl ester Sodium hydride in dimethyl sulfoxide (50 ml) (385 mg, 9.64 mmol) was suspended. Trimethylsulfoxonium iodide (2.02 g, 9.20 mmol) was added little by little to this suspension and stirred at room temperature for 1 hour. The resulting mixture contained 10 ml of 4- [2-oxo-2- (4-oxopiperidin-1-yl) ethyl] piperazine-1-carboxylic acid tert-butyl ester (2.85 g, 8.76 mmol) in DMSO (10 ml). ) The solution was added and stirred for 2 hours at room temperature and 1 hour at 55 ° C. The reaction solution was poured into ice water and extracted with diethyl ether. The organic phase was washed with brine, dried over magnesium sulfate and filtered. The resulting filtrate is concentrated under reduced pressure to give 4- [2- (1-oxa-6-azaspiro [2,5] octan-6-yl) -2-oxoethyl] piperazine-1-carboxylic acid as a white solid. The tert-butyl ester (2.97 g, 99% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.45-1.54 (2H, m), 1.48 (9H, s), 1.78-1.93 (2H, m), 2.44-2.49 (4H, m), 62 (2H, s), 2.73 (2H, s), 3.15-3.36 (2H, m), 3.42-3.47 (2H, m), 3.52-3.68 ( 1 H, m), 3.77-3.88 (1 H, m), 4.02-4.22 (2 H, m).

Reference Example 222
Preparation of 6- (4-Trifluoromethylphenyl) -1-oxa-6-azaspiro [2,5] octane Sodium hydride (361 mg, 9.02 mmol) was suspended in dimethyl sulfoxide (30 ml). Trimethylsulfoxonium iodide (2.00 g, 9.02 mmol) was added little by little to this suspension and stirred at room temperature for 1 hour. To the resulting mixture was added a solution of 1- (4-trifluoromethylphenyl) piperidin-4-one (2.00 g, 8.2 mmol) in DMSO (10 ml) and stirred at room temperature overnight. The reaction solution was poured into ice water and extracted with diethyl ether. The organic phase was washed with brine, dried over sodium sulfate and filtered. The filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (n-hexane / ethyl acetate = 5/1) to give 6- (4-trifluoromethylphenyl) -1-oxa- as a pale yellow solid. 6-Azaspiro [2,5] octane (1.51 g, 72% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.54-1.65 (2H, m), 1.91-2.04 (2H, m), 2.54-2.59 (2H, m), 2.73 (2H, s), 3. 38-3.48 (1 H, m), 3.52-3.62 (1 H, m), 6.95 (2 H, d, J = 8.7 Hz), 7.48 (2 H, d, J = 8) .7 Hz).

Reference Example 223
Preparation of Acetic Acid 3- (2-Methyl-2-Oxiranyl) propyl Ester To a mixture of acetic acid 4-methyl-4-pentenyl ester (5.9 g, 41.5 mmol) prepared in Reference Example 208 and methylene chloride (60 ml) Under ice cooling, m-chloroperbenzoic acid (12.3 g, 71.30 mmol) was gradually added, and the mixture was stirred at room temperature for 2 hours. Under ice-cooling, saturated sodium sulfite aqueous solution and saturated sodium carbonate aqueous solution were added, and the mixture was stirred for 30 minutes and separated. The aqueous phase is further extracted with methylene chloride. The organic phases were combined, washed sequentially with saturated aqueous sodium bicarbonate solution and saturated brine, and dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to obtain acetic acid 3- (2-methyl-2-oxiranyl) propyl ester (6.9 g, quantitative) as a colorless oil.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.33 (3 H, s), 1.56 to 1.79 (4 H, m), 2.05 (3 H, s), 2.52 to 2. 70 (2 H, m), 4.08 (2 H, 2 H, s) t, J = 6.5 Hz).

Reference Example 224
Preparation of 1-ethyl-5- [2- (2-methyl-2-oxiranyl) ethyl] -1H-tetrazole 1-ethyl-5- (3-methyl-3-butenyl) -1H-tetrazole (0.95 g, M-Chloroperbenzoic acid (1.97 g, 7.99 mmol) was added little by little to a solution of 5.71 mmol) in methylene chloride (20 ml) under ice-cooling and further stirred at room temperature for 21 hours. An aqueous solution of sodium thiosulfate and an aqueous solution of sodium hydrogencarbonate were added to the reaction mixture, followed by filtration. The methylene chloride phase was washed with an aqueous solution of sodium hydrogencarbonate, dried over magnesium sulfate and concentrated under reduced pressure. A slightly yellow liquid 1-ethyl-5- [2- (2-methyl-2-oxiranyl) ethyl] -1H-tetrazole (1.2 g, quantitative) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.40 (3 H, s), 1.55 (3 H, t, J = 7.3 Hz), 2.00-2.16 (1 H, m), 2. 20-2. 37 (1 H, m), 2.66 (2H, s), 2.78-2.98 (2H, m), 4.32 (2H, q, J = 7.3 Hz).

  The compounds of Reference Example 225 and Reference Example 226 were produced in the same manner as in Reference Example 224, using the corresponding starting materials.

Reference Example 225
1-phenyl-5- [2- (2-methyl-2-oxiranyl) ethyl] -1H-tetrazole 100% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
1.32 (3H, s), 2.01-2.28 (2H, m), 2.59 (2H, s), 2.92-2.99 (2H, m), 7.43-7. 47 (2 H, m), 7.58-7. 63 (3 H, m).

Reference Example 226
1- (4-chlorophenyl) -5- [2- (2-methyl-2-oxiranyl) ethyl] -1H-tetrazole 100% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
1.33 (3 H, s), 2.00-2.12 (1 H, m), 2.19-2. 31 (1 H, m), 2. 60 (2 H, s), 2. 90-2. 97 (2H, m), 7.39-7. 45 (2H, m), 7.56-7.62 (2H, m).

Reference Example 227
Preparation of 1- (2-methyl-2-oxiranylmethyl) -1,4-dihydrobenzo [d] [1,3] oxazin-2-one 1- (2-methyl-2-propenyl) -1, M-Chloroperbenzoic acid (13.76 g, 55.81 mmol) in a solution of 4-dihydrobenzo [d] [1,3] oxazin-2-one (7.09 g, 34.88 mmol) in methylene chloride (150 ml) ) Was added and stirred at room temperature for 24 hours. An aqueous solution of sodium thiosulfate and an aqueous solution of sodium hydrogencarbonate were added, followed by filtration. The methylene chloride phase was washed with an aqueous solution of sodium hydrogencarbonate, dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (n-hexane / ethyl acetate = 4/1) to obtain a slightly yellow liquid 1- (2-methyl-2-oxiranylmethyl) -1,4-dihydrobenzo [d] [L, 3] oxazin-2-one (5.13 g, 67%) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.39 (3 H, s), 2. 70 (1 H, d, J = 4.4 Hz), 2.78 (1 H, d, J = 4.4 Hz), 3.79 (1 H, d, J = 15) .5 Hz), 4.51 (1 H, d, J = 15.5 Hz), 5.23 (2 H, s), 7.04 to 7.13 (2 H, m), 7.21 to 7.27 (1 H) , M), 7.29-7.38 (1 H, m).

Reference Example 228
Preparation of 3- (2-Methyl-2-oxiranylmethyl) -3H-benzoxazol-2-one 3- (2-Methyl-2-propenyl) -3H-benzoxazol-2-one (1.66 g, To a mixture of 8.77 mmol) and methylene chloride (30 ml) was added m-chloroperbenzoic acid (1.66 g, 9.65 mmol) under ice-cooling, and the mixture was stirred overnight at room temperature. The reaction solution was filtered, and the filtrate was washed successively with 20% aqueous sodium sulfite solution, saturated aqueous sodium bicarbonate solution and saturated brine, and dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue is treated with methylene chloride / n-hexane, and the precipitated crystals are collected by filtration to give 3- (2-methyl-2-oxiranylmethyl) -3H-benzoxazol-2-one (1. 78 g (99% yield) were obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.38 (3 H, s), 2. 73 (1 H, d, J = 4.3 Hz), 2.8 1 (1 H, d, J = 4.3 Hz), 3.68 (1 H, d, J = 15) .0 Hz), 4.26 (1 H, d, J = 15.0 Hz), 7.09-7. 29 (4 H, m).

  The compounds of Reference Example 229 to Reference Example 232 were produced in the same manner as in Reference Example 228 using the corresponding starting materials.

Reference Example 229
5-chloro-3- (2-methyl-2-oxiranylmethyl) -3H-benzoxazol-2-one yield 93%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.38 (3H, s), 2.75 (1H, d, J = 4.2 Hz), 2.79 (1 H, d, J = 4.2 Hz), 3.60 (1 H, d, J = 15) .1 Hz), 4.28 (1 H, d, J = 15.1 Hz), 7.05-7.16 (2 H, m), 7.20-7. 27 (1 H, m).

Reference Example 230
5-fluoro-3- (2-methyl-2-oxiranylmethyl) -3H-benzoxazol-2-one yield 97%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.38 (3H, s), 2.75 (1H, d, J = 4.3 Hz), 2.80 (1 H, d, J = 4.3 Hz), 3.60 (1 H, d, J = 15) .1 Hz), 4.29 (1 H, d, J = 15.1 Hz), 6.75-6.85 (1 H, m), 7.01 (1 H, dd, J = 2.6 Hz, 7.9 Hz) , 7.13 (1 H, dd, J = 4.2 Hz, 8.8 Hz).

Reference Example 231
5-phenyl-3- (2-methyl-2-oxiranylmethyl) -3H-benzoxazol-2-one yield 92%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.40 (3H, s), 2.74 (1H, d, J = 4.3 Hz), 2.82 (1 H, d, J = 4.3 Hz), 3.70 (1 H, d, J = 15) .0 Hz), 4. 32 (1 H, d, J = 15.0 Hz), 7. 25 (1 H, d, J = 8.4 Hz), 7. 29-7. 49 (5 H, m), 7.57 (2H, dd, J = 1.6 Hz, 8.5 Hz).

Reference Example 232
5-bromo-3- (2-methyl-2-oxiranylmethyl) -3H-benzoxazol-2-one yield 80%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.38 (3H, s), 2.75 (1H, d, J = 4.2 Hz), 2.79 (1 H, d, J = 4.2 Hz), 3.61 (1 H, d, J = 15) .1 Hz), 4.27 (1 H, d, J = 15.1 Hz), 7.08 (1 H, d, J = 8.5 Hz), 7.18-7.31 (1 H, m), 7.38 (1 H, d, J = 1.9 Hz).

Reference Example 233
Preparation of 1- (2-methyl-2-oxiranylmethyl) -3-phenyl-1,3-dihydrobenzimidazol-2-one 1- (2-methyl-2-propenyl) -3-phenyl-1, As in Reference Example 228 using 3-dihydrobenzimidazol-2-one (720 mg, 2.72 mmol), 1- (2-methyl-2-oxiranylmethyl) -3-phenyl as a slightly yellow oil There was obtained 1,3-dihydrobenzimidazol-2-one (758 mg, yield 99%).
¹ H-NMR (CDCl ₃ ) δ ppm:
1.40 (3 H, s), 2. 73 (1 H, d, J = 4.5 Hz), 2.86 (1 H, d, J = 4.5 Hz), 3.82 (1 H, d, J = 15) .0 Hz), 4.38 (1 H, d, J = 15.0 Hz), 7.02-7.30 (4 H, m), 7.34-7.45 (1 H, m), 7.50-7 .57 (4H, m).

  The compounds of Reference Example 234 to Reference Example 245 were produced in the same manner as in Reference Example 233, using the corresponding starting materials.

Reference Example 234
1- (4-fluorophenyl) -3- (2-methyl-2-oxiranylmethyl) -1,3-dihydrobenzimidazol-2-one yield 96%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.40 (3H, s), 2.73 (1H, d, J = 4.5 Hz), 2.85 (1 H, d, J = 4.5 Hz), 3.81 (1 H, d, J = 15) .0 Hz), 4.38 (1 H, d, J = 15.0 Hz), 7.00-7.30 (6 H, m), 7.43-7.57 (2 H, m).

Reference Example 235
1- (1-tert-butoxycarbonylpiperidin-4-yl) -3- (2-methyl-2-oxiranylmethyl) -1,3-dihydrobenzimidazol-2-one yield 40%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.34 (3 H, s), 1.54 (9 H, s), 1.71-1. 87 (2 H, m), 2. 20-2. 42 (2 H, m), 2. 70 (1 H, 1 H, m) d, J = 4.5 Hz), 2.71 to 2. 89 (3 H, m), 3. 75 (1 H, d, J = 15.0 Hz), 4.20 to 4.53 (4 H, m), 7.00-7.13 (3 H, m), 7.15-7. 25 (1 H, m).

Reference Example 236
1-methyl-3- (2-methyl-2-oxiranylmethyl) -1,3-dihydrobenzimidazol-2-one yield 68%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.34 (3 H, s), 2.69 (1 H, d, J = 4.5 Hz), 2.78 (1 H, d, J = 4.5 Hz), 3.44 (3 H, s), 76 (1 H, d, J = 15.0 Hz), 4.31 (1 H, d, J = 15.0 Hz), 6.91-7.00 (1 H, m), 7.05-5.25 (3 H) , M).

Reference Example 237
5-chloro-1-methyl-3- (2-methyl-2-oxiranylmethyl) -1,3-dihydrobenzimidazole-2-one yield 89%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.34 (3H, s), 2.70 (1 H, d, J = 4.4 Hz), 2.76 (1 H, d, J = 4.4 Hz), 3.42 (3 H, s), 69 (1 H, d, J = 15.1 Hz), 4.28 (1 H, d, J = 15.1 Hz), 6.88 (1 H, d, J = 8.3 Hz), 7.09 (1 H, dd , J = 1.9 Hz, 8.3 Hz), 7.22 (1 H, d, J = 1.9 Hz).

Reference Example 238
1-methyl-3- (2-methyl-2-oxiranylmethyl) -5-trifluoromethyl-1,3-dihydrobenzimidazole-2-one yield 99%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.36 (3 H, s), 2.71 (1 H, d, J = 4.4 Hz), 2.77 (1 H, d, J = 4.4 Hz), 3.47 (3 H, s), 3. 74 (1 H, d, J = 15.1 Hz), 4.38 (1 H, d, J = 15.1 Hz), 7.04 (1 H, d, J = 8.2 Hz), 7.39 (1 H, dd , J = 1.9 Hz, 8.2 Hz), 7.45 (1 H, d, J = 1.9 Hz).

Reference Example 239
6-chloro-1-methyl-3- (2-methyl-2-oxiranylmethyl) -1,3-dihydrobenzimidazole-2-one yield 99%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.32 (3 H, s), 2.69 (1 H, d, J = 4.6 Hz), 2.75 (1 H, d, J = 4.6 Hz), 3.41 (3 H, s), 68 (1 H, d, J = 15.1 Hz), 4.33 (1 H, d, J = 15.1 Hz), 6.97 (1 H, d, J = 1.9 Hz), 7.07 (1 H, dd , J = 1.9 Hz, 8.4 Hz), 7.13 (1 H, d, J = 8.4 Hz).

Reference Example 240
5-fluoro-1-methyl-3- (2-methyl-2-oxiranylmethyl) -1,3-dihydrobenzimidazole-2-one yield 66%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.34 (3 H, s), 2.70 (1 H, d, J = 4.4 Hz), 2.77 (1 H, d, J = 4.4 Hz), 3.42 (3 H, s), 77 (1 H, d, J = 15.0 Hz), 4.33 (1 H, d, J = 15.0 Hz), 6.74-6. 91 (2 H, m), 7.00 (1 H, dd, J = 2.2 Hz, 8.6 Hz).

Reference Example 241
5-chloro-1-ethyl-3- (2-methyl-2-oxiranylmethyl) -1,3-dihydrobenzimidazole-2-one yield 100%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.25-1.39 (6 H, m), 2.70 (1 H, d, J = 4.4 Hz), 2.76 (1 H, d, J = 4.4 Hz), 3.69 (1 H, d) , J = 15.1 Hz), 3.93 (2 H, q, J = 7.3 Hz), 4.30 (1 H, d, J = 15.1 Hz), 6.90 (1 H, d, J = 8. 3 Hz), 7.07 (1 H, dd, J = 2.0 Hz, 8.3 Hz), 7.23 (1 H, d, J = 2.0 Hz).

Reference Example 242
5-chloro-1-isopropyl-3- (2-methyl-2-oxiranylmethyl) -1,3-dihydrobenzimidazole-2-one 100% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
1.34 (3H, s), 1.53 (6H, dd, J = 2.1 Hz, 6.7 Hz), 2.70 (1 H, d, J = 4.5 Hz), 2.75 (1 H, d , J = 4.5 Hz), 3.68 (1 H, d, J = 15.1 Hz), 4.28 (1 H, d, J = 15.1 Hz), 4.65-4.79 (1 H, m) , 7.04 (2H, s), 7.22 (1 H, s).

Reference Example 243
5-dimethylamino-1-methyl-3- (2-methyl-2-oxiranylmethyl) -1,3-dihydrobenzimidazol-2-one 100% yield
¹ H-NMR (DMSO-d ₆ ) δ ppm:
1.33 (3H, s), 2.69 (1 H, d, J = 4.5 Hz), 2.79 (1 H, d, J = 4.5 Hz), 2.92 (6 H, s), 39 (3H, s), 3.67 (1H, d, J = 15.0 Hz), 4.32 (1 H, d, J = 15.0 Hz), 6.55 (1 H, dd, J = 2.4 Hz , 8.6 Hz), 6.71 (1 H, d, J = 2.4 Hz), 6.85 (1 H, d, J = 8.6 Hz).

Reference Example 244
5-chloro-1- (n-hexyl) -3- (2-methyl-2-oxiranylmethyl) -1,3-dihydrobenzimidazol-2-one yield 100%
¹ H-NMR (CDCl ₃ ) δ ppm:
0.87 (3H, t, J = 6.9 Hz), 1.18-1.43 (9 H, m), 1.64-1.80 (2 H, m), 2.70 (1 H, d, J = 4.4 Hz), 2.75 (1 H, d, J = 4.4 Hz), 3.69 (1 H, d, J = 15.0 Hz), 3.86 (2 H, t, J = 7.4 Hz) , 4.30 (1 H, d, J = 15.0 Hz), 6. 88 (1 H, d, J = 8.4 Hz), 7.06 (1 H, dd, J = 1.9 Hz, 8.4 Hz), 7.22 (1 H, d, J = 1.9 Hz).

Reference Example 245
5-ethoxycarbonyl-1-methyl-3- (2-methyl-2-oxiranylmethyl) -1,3-dihydrobenzimidazole-2-one 100% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
1.32-1.43 (6 H, m), 2.69 (1 H, d, J = 4.5 Hz), 2.78 (1 H, d, J = 4.5 Hz), 3.47 (3 H, s) ), 3.87 (1 H, d, J = 15.0 Hz), 4.28 (1 H, d, J = 15.0 Hz), 4.39 (2 H, q, J = 7.2 Hz), 7.00 (1H, d, J = 8.2 Hz), 7.85 (1 H, d, J = 1.5 Hz), 7.90 (1 H, dd, J = 1.5 Hz, 8.2 Hz).

Reference Example 246
Preparation of 1-Benzyl-3- (2-methyl-2-oxiranylmethyl) imidazolidin-2-one 1-Benzyl-3- (2-methyl-2-propenyl) imidazolidin-2-one (1. Using 63 g (7.05 mmol) of 1-benzyl-3- (2-methyl-2-oxiranylmethyl) imidazolidin-2-one as a pale yellow oil (680 mg, 39% rate).
¹ H-NMR (CDCl ₃ ) δ ppm:
1.35 (3 H, s), 2.62 (1 H, d, J = 4.7 Hz), 2.69 (1 H, d, J = 4.7 Hz), 3.05-3.25 (3 H, m) ), 3.27-3.49 (2H, m), 3.61 (1H, d, J = 14.6 Hz), 4.39 (2H, s), 7.20-7.34 (5H, m) ).

  The compounds of Reference Example 247 to Reference Example 2 were produced in the same manner as in Reference Example 247 using the corresponding starting materials.

Reference Example 247
1- (2-methyl-2-oxiranylmethyl) -3-phenylimidazolidin-2-one yield 58%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.37 (3H, s), 2.65 (1 H, d, J = 4.6 Hz), 2.72 (1 H, d, J = 4.6 Hz), 3.18 (1 H, d, J = 14) .7 Hz), 3.48-3.61 (2H, m), 3.64 (1 H, d, J = 14.7 Hz), 3.77-3.91 (2 H, m), 7.03 (1 H) , T, J = 7.3 Hz), 7.25-7.36 (2 H, m), 7.56 (2 H, d, J = 7.9 Hz).

Reference Example 248
1- (4-fluorobenzyl) -3- (2-methyl-2-oxiranylmethyl) imidazolidin-2-one yield 34%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.35 (3H, s), 2.62 (1H, d, J = 4.7 Hz), 2.68 (1 H, d, J = 4.7 Hz), 3.12 (1 H, d, J = 14) .6 Hz), 3.16-3.20 (2 H, m), 3. 27-3. 45 (2 H, m), 3.6 1 (1 H, d, J = 14.6 Hz), 4. 35 (2 H) , S), 6.89-7.07 (2H, m), 7.14-7.27 (2H, m).

Reference Example 249
1- (4-bromobenzyl) -3- (2-methyl-2-oxiranylmethyl) imidazolidin-2-one yield 51%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.34 (3H, s), 2.62 (1H, d, J = 4.7 Hz), 2.67 (1 H, d, J = 4.7 Hz), 3.12 (1 H, d, J = 14) .7 Hz), 3.16 to 3.25 (2 H, m), 3.27-3. 50 (2 H, m), 3.61 (1 H, d, J = 14.7 Hz), 4.33 (2 H) , S), 7.15 (2 H, d, J = 8.4 Hz), 7. 45 (2 H, d, J = 8.4 Hz).

Reference Example 250
1- (4-methoxybenzyl) -3- (2-methyl-2-oxiranylmethyl) imidazolidin-2-one yield 43%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.34 (3H, s), 2.61 (1 H, d, J = 4.7 Hz), 2.67 (1 H, d, J = 4.7 Hz), 3.07-3.23 (3 H, m) , 3.27-3.50 (2H, m), 3.58 (1 H, d, J = 14.6 Hz), 3.80 (3 H, s), 4.32 (2 H, s), 6. 86 (2H, d, J = 8.4 Hz), 7.19 (2H, d, J = 8.4 Hz).

Reference Example 251
Preparation of 1- (4-Chlorobenzyl) -3- (2-methyl-2-oxiranylmethyl) imidazolidin-2-one Toluene-4-sulfonic acid 2-methyl-2-oxiranyl methyl ester (500 mg) , 2.37 mmol) was dissolved in 5 ml of DMF, sodium hydride (99 mg, 2.49 mmol) was added under ice-cooling, and the mixture was stirred at room temperature for 1 hour. A solution of 1- (4-chlorobenzyl) imidazolidin-2-one (633 mg, 2.61 mmol) dissolved in 5 ml of DMF was added under ice-cooling and stirred overnight at room temperature. Water was added to the reaction solution and extracted twice with diethyl ether. The organic phases were combined, washed twice with water, then washed with saturated brine and dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (n-hexane / acetone = 3/1) to give 1- (4-chlorobenzyl) -3- (2-methyl-2-oxiranylmethyl) imidazolidine as a slightly yellow oil. -2-one (399 mg, 60%) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.35 (3 H, s), 2.62 (1 H, d, J = 4.7 Hz), 2.68 (1 H, d, J = 4.7 Hz), 3.05-3.25 (3 H, m) ), 3.27-3.49 (2H, m), 3.61 (1H, d, J = 14.7 Hz), 4.35 (2H, s), 7.21 (2H, dd, J = 2) .0 Hz, 6.7 Hz), 7.30 (2 H, dd, J = 2.0 Hz, 6.7 Hz).

  The compounds of Reference Example 252 and Reference Example 253 were produced in the same manner as in Reference Example 251 using the corresponding starting materials.

Reference Example 252
1- (1-benzylpiperidin-4-yl) -3- (2-methyl-2-oxiranylmethyl) imidazolidin-2-one yield 54%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.35 (3 H, s), 1.59-1.80 (4 H, m), 2.00-2.16 (2 H, m), 2. 60 (1 H, d, J = 4.7 Hz), 2.66 (1 H, d, J = 4.7 Hz), 2.84-3.00 (2 H, m), 3.07 (1 H, d, J = 14.6 Hz), 3.22-3.43 (4H, m), 3.50 (2H, s), 3.54 (1 H, d, J = 14.7 Hz), 3.68-3.86 (1 H, m), 7.16-7.34 (5H, m).

Reference Example 253
1- (2,4-dimethoxybenzyl) -3- (2-methyl-2-oxiranylmethyl) imidazolidin-2-one yield 40%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.34 (3 H, s), 2. 60 (1 H, d, J = 4.7 Hz), 2. 67 (1 H, d, J = 4.7 Hz), 3. 10 (1 H, d, J = 14) .6 Hz), 3.14-3.34 (4 H, m), 3.56 (1 H, d, J = 14.6 Hz), 3.80 (6 H, s), 4. 35 (2 H, s), 6.32-6.43 (2H, m), 7.18 (1 H, d, J = 8.9 Hz).

Reference Example 254
Preparation of 1- (2-methyl-2-oxiranylmethyl) pyrrolidine-2,5-dione Analogously to Reference Example 228 using 1- (2-methyl-2-propenyl) pyrrolidine-2,5-dione Thus, 1- (2-methyl-2-oxiranylmethyl) pyrrolidine-2,5-dione was prepared.
86% yield
¹ H-NMR (DMSO-d ₆ ) δ ppm:
1.34 (3 H, s), 2.58 (1 H, d, J = 4.6 Hz), 2.67-2.79 (5 H, m), 3.56 (1 H, d, J = 13.9 Hz ), 3.84 (1 H, d, J = 13.9 Hz).

Reference Example 255
Preparation of 2- (2-Methyl-2-oxiranylmethyl) phthalimide In the same manner as in Reference Example 228 using 2- (2-methyl-2-propenyl) phthalimide, 2- (2-methyl-2-oxy) Ranylmethyl) phthalimide was prepared.
98% yield
¹ H-NMR (DMSO-d ₆ ) δ ppm:
1.38 (3H, s), 2.62 (1H, d, J = 4.6 Hz), 2.82 (1 H, d, J = 4.6 Hz), 3.71 (1 H, d, J = 14) .3 Hz), 4.01 (1 H, d, J = 14.3 Hz), 7.73 (2 H, dd, J = 2.9 Hz, 8.6 Hz), 7.87 (2 H, dd, J = 2. 9 Hz, 8.6 Hz).

Reference Example 256
Preparation of 1- (2-methyl-2-oxiranylmethyl) -1H-benzimidazole Using 1- (2-methyl-2-propenyl) -1H-benzoimidazole, in the same manner as in Reference Example 228, (2-Methyl-2-oxiranylmethyl) -1H-benzimidazole was prepared.
11% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
1.32 (3H, s), 2.60 (1 H, d, J = 4.4 Hz), 2.71 (1 H, d, J = 4.4 Hz), 4.17 (1 H, d, J = 15) .1 Hz), 4.44 (1 H, d, J = 15.1 Hz), 7.23-7.41 (2 H, m), 7.48 (1 H, dd, J = 2.2 Hz, 7.8 Hz) , 7.80 (1 H, dd, J = 2.2 Hz, 7.8 Hz), 7.93 (1 H, s).

Reference Example 257
Preparation of 1- (2-methyl-2-oxiranylmethyl) -1H-imidazole By using 1- (2-methyl-2-propenyl) -1H-imidazole in the same manner as in Reference Example 228, 1- (2 -Methyl-2-oxiranylmethyl) -1H-imidazole was prepared.
53% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
1.26 (3H, s), 2.57 (1H, d, J = 4.4 Hz), 2.69 (1 H, d, J = 4.4 Hz), 3.94 (1 H, d, J = 14) .7 Hz), 4.16 (1 H, d, J = 14.7 Hz), 6.97 (1 H, s), 7.08 (1 H, s), 7.49 (1 H, s).

Reference Example 258
Preparation of 3- [3- (2-Methyl-2-oxiranyl) propyl] -3H-benzoxazol-2-one 3- (4-Methyl-4-pentenyl) -3H-benzoxazol-2-one (3. In the same manner as in Reference Example 228, 4 g (15.65 mmol) of 3- [3- (2-Methyl-2-oxiranyl) propyl] -3H-benzoxazol-2-one (3. 3) was obtained in the same manner as in Reference Example 228. 8 g (quantitative) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.33 (3H, s), 1.56-1.77 (2H, m), 1.80-1.95 (2H, m), 2.59 (1 H, d, J = 4.8 Hz), 2.63 (1 H, d, J = 4.8 Hz), 3.85 (2 H, t, J = 7.4 Hz), 6.99 (1 H, d, J = 7.9 Hz), 7.05-7 .23 (3 H, m).

Reference Example 259
Preparation of 3- [4- (2-Methyl-2-oxiranyl) butyl] -3H-benzoxazol-2-one 3- (5-Methyl-5-hexenyl) -3H-benzoxazol-2-one (1. In the same manner as in Reference Example 228 using 1 g (4.8 mmol), 3- [4- (2-methyl-2-oxiranyl) butyl] -3H-benzoxazol-2-one (1.2 g) as a colorless oil , Quantitative).
¹ H-NMR (CDCl ₃ ) δ ppm:
1.30 (3H, s), 1.42-1.67 (4H, m), 1.74-1.88 (2H, m), 2.57 (1 H, d, J = 4.9 Hz), 2.60 (1H, d, J = 4.9 Hz), 3.84 (2H, t, J = 7.2 Hz), 6.98 (1 H, d, J = 8.1 Hz), 7.02-7 .30 (3 H, m).

Reference Example 260
Preparation of 3- (2-Methyl-2-oxiranylmethyl) oxazolidin-2-one Using 3- (2-Methyl-2-propenyl) oxazolidin-2-one (4.28 g, 30.35 mmol), The method of Reference Example 228 gave 3- (2-methyl-2-oxiranylmethyl) oxazolidin-2-one (2.87 g, yield 62%) as a colorless oil.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.36 (3H, s), 2.66 (1H, d, J = 4.5 Hz), 2.70 (1 H, d, J = 4.5 Hz), 3.15 (1 H, d, J = 14) .7 Hz), 3.57-3.75 (3 H, m), 4.25-4. 39 (2 H, m).

Reference Example 261
Preparation of 3,3-Difluoro-1- (2-methyl-2-oxiranylmethyl) -1,3-dihydroindol-2-one 3,3-Difluoro-1- (2-methyl-2-propenyl) In the same manner as in Reference Example 228 using 1,3-dihydroindol-2-one (1.08 g, 4.83 mmol), 3,3-difluoro-1- (2-methyl-2) as a slightly yellow powder -Oxiranylmethyl) -1,3-dihydroindol-2-one (1.14 g, 99% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.35 (3 H, s), 2.71 (1 H, d, J = 4.3 Hz), 2.77 (1 H, d, J = 4.3 Hz), 3.46 (1 H, d, J = 15) .0 Hz), 4.26 (1 H, d, J = 15.0 Hz), 7.12-7.24 (2 H, m), 7.45-7.61 (2 H, m).

  The compounds of Reference Example 262 and Reference Example 263 were produced in the same manner as in Reference Example 261 using the corresponding starting materials.

Reference Example 262
3,3-Dimethyl-1- (2-methyl-2-oxiranylmethyl) -1,3-dihydroindol-2-one
¹ H-NMR (CDCl ₃ ) δ ppm:
1. 31 (3 H, s), 1. 39 (6 H, s), 2. 67 (1 H, d, J = 4.5 Hz), 2. 74 (1 H, d, J = 4.5 Hz), 3. 53 (1 H, d, J = 14.0 Hz), 4.22 (1 H, d, J = 14.0 Hz), 7.00-7.10 (2 H, m), 7.16-7. 31 (2 H) , M).

Reference Example 263
1- (2-Methyl-2-oxiranylmethyl) -1,3-dihydroindol-2-one
¹ H-NMR (CDCl ₃ ) δ ppm:
1.34 (3H, s), 2.67 (1 H, d, J = 4.5 Hz), 2.76 (1 H, d, J = 4.5 Hz), 3.49-3.61 (3 H, m) ), 4.22 (1 H, d, J = 14.9 Hz), 7.00-7.10 (2 H, m), 7.18-7. 35 (2 H, m).

Reference Example 264
Preparation of (2-methyl-2-oxiranylmethyl) carbamic acid benzyl ester N- (2-methyl-2-propenyl) carbamic acid benzyl ester (3.90 g, 19.0 mmol) prepared in Reference Example 173 was used. Dissolve in methylene chloride (80 ml), add m-chloroperbenzoic acid (5.15 g, 20.9 mmol) and stir at room temperature overnight. Aqueous sodium thiosulfate solution and saturated aqueous sodium hydrogen carbonate solution were added, and after stirring for a while, the layers were separated. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to give colorless liquid (2-methyl-2-oxiranylmethyl) carbamic acid benzyl ester (4.31 g, quantitative).
¹ H-NMR (CDCl ₃ ) δ ppm:
1.35 (3 H, s), 2.61 (1 H, d, J = 4.5 Hz), 2.72 (1 H, d, J = 4.5 Hz), 3.28-3.53 (2 H, m) ), 4.90 (1 H, br), 5.11 (2 H, s), 7.26-7.44 (5 H, m).

  The compounds of Reference Example 265 to Reference Example 276 were produced in the same manner as in Reference Example 264, using the corresponding starting materials.

Reference Example 265
N-Methyl-N- (2-methyl-2-oxiranylmethyl) carbamic acid benzyl ester yield 42%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.26 (1.5 H, s), 1.31 (1.5 H, s), 2.57 (1 H, s), 2.61 (1 H, s), 2.99 (3 H, s), 3 24 (1 H, d, J = 15.1 Hz), 3.62 (0.5 H, d, J = 15.1 Hz), 3.72 (0.5 H, d, J = 15.1 Hz), 5. 14 (2 H, s), 7. 27-7. 41 (5 H, m).

Reference Example 266
(2-Methyl-2-oxiranylmethyl) carbamic acid 4-chlorobenzyl ester yield 98%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.35 (3H, s), 2.62 (1 H, d, J = 4.4 Hz), 2.71 (1 H, d, J = 4.4 Hz), 3.27-3.50 (2 H, m) ), 4.88 (1 H, br), 5.06 (2 H, s), 7.23 to 7.41 (4 H, m).

Reference Example 267
(2-Methyl-2-oxiranylmethyl) carbamic acid 4-fluorobenzyl ester 100% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
1.34 (3 H, s), 2.61 (1 H, d, J = 4.5 Hz), 2.71 (1 H, d, J = 4.5 Hz), 3.32-3.50 (2 H, m) ), 4.86 (1 H, br), 5.06 (2 H, s), 6.95 to 7.09 (2 H, m), 7. 27 to 7.41 (2 H, m).

Reference Example 268
(2-Methyl-2-oxiranylmethyl) carbamic acid ethyl ester yield 82%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.24 (3 H, t, J = 7.1 Hz), 1.35 (3 H, s), 2.62 (1 H, d, J = 4.5 Hz), 2.74 (1 H, d, J = 4 .5 Hz), 3.27-3.50 (2 H, m), 4.12 (2 H, q, J = 7.1 Hz), 4.78 (1 H, br).

Reference Example 269
(2-Methyl-2-oxiranylmethyl) carbamic acid 4-trifluoromethoxybenzyl ester yield 99%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.35 (3 H, s), 2.62 (1 H, d, J = 4.4 Hz), 2.71 (1 H, d, J = 4.4 Hz), 3.42 (2 H, d, J = 5 .6 Hz), 4.90 (1 H, br), 5. 10 (2 H, s), 7. 20 (2 H, d, J = 8.3 Hz), 7.38 (2 H, d, J = 8.3 Hz ).

Reference Example 270
N-methyl-N- (2-methyl-2-oxiranylmethyl) carbamic acid 4-fluorobenzyl ester yield 73%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.25 (1.5 H, s), 1.30 (1.5 H, s), 2.56 (1 H, s), 2.61 (1 H, s), 2.97 (3 H, s), 3 22 (1 H, d, J = 14.8 Hz), 3.61 (0.5 H, d, J = 14.8 Hz), 3.72 (0.5 H, d, J = 14.8 Hz), 5. 10 (2H, s), 6.95 to 7.09 (2H, m), 7.27 to 7.41 (2H, m).

Reference Example 271
Oxylanylmethylcarbamic acid 4-chlorobenzyl ester yield 97%
¹ H-NMR (CDCl ₃ ) δ ppm:
2.59 (1 H, dd, J = 2.6 Hz, 4.6 Hz), 2.79 (1 H, t, J = 4.3 Hz), 3.11 (1 H, br), 3.20-3.32 (1H, m), 3.50 to 3.73 (1H, m), 4.93 (1H, br), 5.07 (2H, s), 7.23 to 7.41 (4H, m).

Reference Example 272
Oxyranyl methyl carbamic acid 4-fluorobenzyl ester 89% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
2.59 (1H, dd, J = 2.6 Hz, 4.6 Hz), 2.79 (1 H, t, J = 4.3 Hz), 3.11 (1 H, br), 3.21-3.32 (1H, m), 3.45-3. 73 (1 H, m), 4.92 (1 H, br), 5.07 (2 H, s), 6.95-7.09 (2 H, m), 7.27-7.41 (2H, m).

Reference Example 273
N-methyl-N-oxiranyl methyl carbamic acid 4-fluorobenzyl ester 34% yield,
¹ H-NMR (CDCl ₃ ) δ ppm:
2.51 (1H, br), 2.76 (1H, br), 3.01 (3H, s), 3.02-3.27 (2H, m), 3.55-3.91 (1H, 1H, s) m), 5.10 (2H, s), 6.95 to 7.09 (2H, m), 7.27 to 7.41 (2H, m).

Reference Example 274
Oxiranylmethylcarbamic acid tert-butyl ester yield 83%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.45 (9 H, s), 2.59 (1 H, dd, J = 2.6 Hz, 4.6 Hz), 2.78 (1 H, t, J = 4.4 Hz), 3.09 (1 H, br) ), 3.16-3.28 (1 H, m), 3. 38-3. 66 (1 H, br), 4.53-4. 91 (1 H, br).

Reference Example 275
Oxyranyl methyl carbamic acid benzyl ester yield 72%
¹ H-NMR (DMSO-d ₆ ) δ ppm:
2.67 (1 H, t, J = 4.5 Hz), 2.91-3. 32 (4 H, m), 4.91-5.09 (3 H, m), 7.23-7. 55 (5 H) , M).

Reference Example 276
Oxiranylmethyl carbamic acid phenyl ester yield 90%
¹ H-NMR (DMSO-d ₆ ) δ ppm:
2.57 (1 H, dd, J = 2.5 Hz, 5.0 Hz), 2.73 (1 H, t, J = 4.5 Hz), 3.00-3.45 (3 H, m), 7.10 (2H, d, J = 7.6 Hz), 7.20 (1 H, t, J = 7.6 Hz), 7.38 (2 H, t, J = 7.6 Hz), 7.94 (1 H, br) .

Reference Example 277
Preparation of (4-chlorophenyl) carbamic acid (2-methyl-2-oxiranylmethyl) ester Methylene chloride of (4-chlorophenyl) carbamic acid 2-methyl-2-propenyl ester (1.0 g, 4.4 mmol) To a solution (20 ml) was added m-chloroperbenzoic acid (1.6 g, 6.6 mmol) under ice-cooling and stirring, and the mixture was stirred at room temperature for 4 hours. An aqueous solution of sodium thiosulfate is added, and the reaction mixture is filtered, sodium bicarbonate and water are added thereto, and the mixture is separated, dried over magnesium sulfate and concentrated under reduced pressure to give (4-chlorophenyl) carbamic acid (2- Methyl-2-oxiranylmethyl) ester (1.1 g, quantitative) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.42 (3 H, s), 2.71 (1 H, d, J = 4.6 Hz), 2.82 (1 H, d, J = 4.6 Hz), 4.01 (1 H, d, J = 11) .9 Hz), 4.37 (1 H, d, J = 11.9 Hz), 6.79 (1 H, br), 7.23-7.37 (4 H, m).

Reference Example 278
Preparation of N- (4-chlorophenyl) -N-methylcarbamic acid (2-methyl-2-oxiranylmethyl) ester N- (4-chlorophenyl) -N-methylcarbamic acid 2-methyl-2-propenyl ester (1. M-Chloroperbenzoic acid (2.5 g, 10.1 mmol) was added to a solution of 78 g (6.7 mmol) in methylene chloride (20 ml) with ice-cooling and stirring at room temperature for 6.5 hours. An aqueous solution of sodium thiosulfate is added, and the reaction mixture is filtered, sodium hydrogen carbonate and water are added thereto, and the mixture is separated, dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / methanol = 20/1) to give a slightly yellow liquid N- (4-chlorophenyl) -N-methylcarbamic acid (2-methyl-2-oxiranylmethyl) ester (2-methyl-2-oxiranylmethyl) ester 1.7 g (quantitative) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.32 (3 H, s), 2.62 (1 H, d, J = 4.6 Hz), 2.69 (1 H, d, J = 4.6 Hz), 3.30 (3 H, s), 3. 99 (1 H, d, J = 11.8 Hz), 4.30 (1 H, d, J = 11.8 Hz), 7.15 to 7.25 (2 H, m), 7.31 to 7.38 (2 H) , M).

Reference Example 279
Preparation of 4-oxiranylmethylpiperazine-1-carboxylic acid tert-butyl ester Piperazine-1-carboxylic acid tert-butyl ester (6.2 g, 33.29 mmol), epibromohydrin (5.4 g, 39. A mixture of 42 mmol) and potassium carbonate (5.5 g, 39.79 mmol) in acetonitrile (70 ml) was heated to reflux for 3 hours. The reaction solution was concentrated under reduced pressure, water was added, and the mixture was extracted with methylene chloride. The extract was washed with saturated brine, dried over sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) to give 4-oxiranylmethylpiperazine-1-carboxylic acid tert-butyl ester (6.2 g, yield 77%) as a colorless oil.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.46 (9 H, s), 2.21-2. 60 (6 H, m), 2. 70-2.81 (2 H, m), 3.05-3. 12 (1 H, m), 3. 35-3.56 (4H, m).

Reference Example 280
Preparation of [4- (2-Methyl-2-oxiranylmethyl) piperazin-1-yl] carbamic acid tert-butyl ester Toluene-4-sulfonic acid (2-methyl-2-oxiranylmethyl) ester (9) .75 g (40.3 mmol) and piperazin-1-yl-carbamic acid tert-butyl ester (6.75 g, 33.5 mmol) prepared in Reference Example 36 were dissolved in DMF (70 ml). To this solution was added triethylamine (7 ml, 50.3 mmol) and potassium iodide (6.68 g, 33.5 mmol) and stirred at room temperature overnight. After extraction with ethyl acetate, the organic phases were combined, washed with water and saturated brine, dried over sodium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (hexane / acetone = 4/1) to give [4- (2-methyl-2-oxiranylmethyl) piperazin-1-yl] carbamic acid tert-butyl ester as white powder crystals. (4.66 g, 51% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.35 (3 H, s), 1.46 (9 H, s), 2.31 (1 H, d, J = 12.9 Hz), 2.49-2.84 (11 H, m), 5.37 ( 1H, br).

Reference Example 281
Preparation of 3- (2-Methyl-2-oxiranylmethyl) -5- (4-trifluoromethoxyphenyl) -3H- [1,3,4] oxadiazol-2-one Prepared according to Reference Example 49 5- (4-Trifluoromethoxyphenyl) -3H- [1,3,4] oxadiazol-2-one (3.18 g, 12.92 mmol) and toluene-4-sulfonic acid (2-methyl-2) Potassium carbonate (2.14 g, 15.50 mmol) and sodium iodide (2.90 g, 19.38 mmol) in a solution of oxiranylmethyl) ester (4.80 g, 19.38 mmol) in DMF (30 ml) ) Was added and stirred at room temperature for 24 hours and further at 60 ° C. for 4 hours. To the reaction solution was added water, extracted with ethyl acetate, washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (hexane / ethyl acetate = 9/1) to give 3- (2-methyl-2-oxiranylmethyl) -5- (4-trifluoromethoxyphenyl) -3H as a white solid. -[1,3,4] oxadiazol-2-one (2.37 g, yield 58%) was obtained.
¹ H-NMR (DMSO-d ₆ ) δ ppm:
1.43 (3H, s), 2.72 (1 H, d, J = 4.4 Hz), 2.86 (1 H, d, J = 4.4 Hz), 3.93 (2 H, dd, J = 14) .8 Hz, 22.2 Hz), 7.28-7.41 (2H, m), 7.83-7.98 (2H, m).

  In analogy to Reference Example 281 using 5-substituted-3H- [1,3,4] oxadiazol-2-one and toluene-4-sulfonic acid (2-methyl-2-oxiranylmethyl) ester The compounds of Reference Example 282 to Reference Example 289 were produced.

Reference Example 282
3- (2-Methyl-2-oxiranylmethyl) -5-phenyl-3H- [1,3,4] oxadiazol-2-one yield 41%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.44 (3 H, s), 2.72 (1 H, d, J = 4.5 Hz), 2.88 (1 H, d, J = 4.5 Hz), 3.87 (1 H, d, J = 14) .7 Hz), 3.99 (1 H, d, J = 14.7 Hz), 7.40-7.57 (3 H, m), 7.79-7.87 (2 H, m).

Reference Example 283
3- (2-Methyl-2-oxiranylmethyl) -5- (4-trifluoromethylphenyl) -3H- [1,3,4] oxadiazol-2-one yield 34%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.45 (3H, s), 2.73 (1H, d, J = 4.5 Hz), 2.87 (1 H, d, J = 4.5 Hz), 3.92 (1 H, d, J = 14) .8 Hz), 4.00 (1 H, d, J = 14.8 Hz), 7.75 (2 H, d, J = 8.3 Hz), 8.01 (2 H, d, J = 8.3 Hz).

Reference Example 284
3- (2-Methyl-2-oxiranylmethyl) -5- (4-biphenylyl) -3H- [1,3,4] oxadiazol-2-one yield 38%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.45 (3H, s), 2.73 (1H, d, J = 4.5 Hz), 2.89 (1 H, d, J = 4.5 Hz), 3.89 (1 H, d, J = 14) .8 Hz), 4.00 (1 H, d, J = 14.8 Hz), 7.33-7.50 (3 H, m), 7.57-7. 75 (4 H, m), 7.93 (2 H) , D, J = 8.6 Hz).

Reference Example 285
3- (2-Methyl-2-oxiranylmethyl) -5- (4-chlorophenyl) -3H- [1,3,4] oxadiazol-2-one yield 52%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.44 (3 H, s), 2.72 (1 H, d, J = 4.4 Hz), 2.86 (1 H, d, J = 4.4 Hz), 3.89 (1 H, d, J = 14) .8 Hz), 3.97 (1 H, d, J = 14.8 Hz), 7.46 (2 H, d, J = 8.7 Hz), 7.80 (2 H, d, J = 8.7 Hz).

Reference Example 286
3- (2-Methyl-2-oxiranylmethyl) -5- (4-fluorophenyl) -3H- [1,3,4] oxadiazol-2-one yield 72%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.43 (3 H, s), 2.72 (1 H, d, J = 4.5 Hz), 2.87 (1 H, d, J = 4.5 Hz), 3.88 (1 H, d, J = 14) .7 Hz), 3.96 (1 H, d, J = 14.7 Hz), 7.11-7.21 (2 H, m), 7.74-7. 89 (2 H, m)
Reference Example 287
3- (2-Methyl-2-oxiranylmethyl) -5- [2- (4-chlorophenyl) ethyl] -3H- [1,3,4] oxadiazol-2-one yield 78%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.32 (3H, s), 2.64 (1H, d, J = 4.5 Hz), 2.72 (1 H, d, J = 4.5 Hz), 2.79-2.90 (2H, m) ), 2.93-3.04 (2H, m), 3.74 (1 H, d, J = 14.8 Hz), 3.79 (1 H, d, J = 14.8 Hz), 7.12 (2 H) , D, J = 8.6 Hz), 7.27 (2 H, d, J = 8.6 Hz)
Reference Example 288
3- (2-Methyl-2-oxiranylmethyl) -5- [2- (4-chlorophenyl) vinyl] -3H- [1,3,4] oxadiazol-2-one yield 100%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.41 (3 H, s), 2.71 (1 H, d, J = 4.4 Hz), 2.83 (1 H, d, J = 4.4 Hz), 3.88 (2 H, s), 6. 60 (1 H, d, J = 16.4 Hz), 7.28-7.47 (5 H, m).

Reference Example 289
3- (2-Methyl-2-oxiranylmethyl) -5- (4-chlorophenoxymethyl) -3H- [1,3,4] oxadiazol-2-one yield 59%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.37 (3 H, s), 2.68 (1 H, d, J = 4.4 Hz), 2.78 (1 H, d, J = 4.4 Hz), 3.86 (2 H, s), 4. 90 (2H, s), 6.91 (2H, dd, J = 2.3 Hz, 6.9 Hz), 7.29 (2 H, dd, J = 2.3 Hz, 6.9 Hz).

Reference Example 290
Preparation of 2- (2-Methyl-2-oxiranylmethyl) -1,1-dioxo-1,2-dihydrobenzo [d] isothiazol-3-one Saccharin and toluene-4-sulfonic acid 2-methyl- In the same manner as in Reference Example 281 from 2-oxiranylmethyl ester, 2- (2-methyl-2-oxiranylmethyl) -1,1-dioxo-1,2-dihydrobenzo [d] isothiazole-3 -Manufactured on.
White powder crystal yield 43%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.49 (3H, s), 2.74 (1H, d, J = 4.5 Hz), 2.96 (1 H, d, J = 4.5 Hz), 3.73 (1 H, d, J = 15) .5 Hz), 4.04 (1 H, d, J = 15.5 Hz), 7.81-8.00 (3 H, m), 8.09 (1 H, dd, J = 2.4 Hz, 6.6 Hz) .

Reference Example 291
Preparation of 1- (2-methyl-2-oxiranylmethyl) piperidin-4-one In the same manner as in Reference Example 281 using 4-piperidone hydrochloride, 1- (2-methyl-2-oxy) Ranylmethyl) piperidin-4-one was prepared.
Colorless oil, 50% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
1.43 (3 H, s), 2.35 to 2.51 (5 H, m), 2.58 to 2.93 (7 H, m).

Reference Example 292
Preparation of 4- (2-methyl-2-oxiranylmethyl) -1- (4-trifluoromethylbenzyl) piperazin-2-one Using 1- (4-trifluoromethylbenzyl) piperazin-2-one In the same manner as in Reference Example 281, 4- (2-methyl-2-oxiranylmethyl) -1- (4-trifluoromethylbenzyl) piperazin-2-one was produced.
Colorless powdery crystals, yield 63%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.37 (3 H, s), 2. 34 (1 H, d, J = 12.9 Hz), 2.53-2.67 (4 H, m), 2.77-2.91 (1 H, m), 3.14-3.37 (4H, m), 4.62 (1 H, d, J = 15.1 Hz), 4.69 (1 H, d, J = 15.1 Hz), 7.38 (2 H, d , J = 8.2 Hz), 7.60 (2 H, d, J = 8.2 Hz).

Reference Example 293
Preparation of 4- (2-methyl-2-oxiranylmethyl) -1- (tert-butyl) piperazin-2-one Analogously to Reference Example 281 using 1- (tert-butyl) piperazin-2-one Then, 4- (2-methyl-2-oxiranylmethyl) -1- (tert-butyl) piperazin-2-one was prepared.
Colorless powdery crystals, 39% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
1.38 (3H, s), 1.45 (9H, s), 2.31 (1H, d, J = 12.9 Hz), 2.42 to 2.55 (4 H, m), 2.74 2.88 (1 H, m), 3.02 (1 H, d, J = 16.1 Hz), 3. 20 (1 H, d, J = 16.1 Hz), 3.28-3.37 (2 H, m) ).

Reference Example 294
Preparation of (S) -1- (2-Methyl-2-oxiranylmethyl) -4- (4-trifluoromethoxyphenyl) piperazine (R) -Toluene-4-sulfonic acid (2-methyl-2-oxy) Triethylamine (0.55 ml) in a solution of lanylmethyl) ester (0.80 g, 3.30 mmol) and 1- (4-trifluoromethoxyphenyl) piperazine (0.91 g, 3.36 mmol) in DMF (8 ml) , 3.96 mmol) and stirred for a further 22 hours at room temperature. To the reaction solution was added water, extracted with ethyl acetate, washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / methanol = 100/1) to give a slightly yellow liquid (S) -1- (2-methyl-2-oxiranylmethyl) -4- (4-trifluoro) Methoxyphenyl) piperazine (0.46 g, 44% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.40 (3 H, s), 2. 34 (1 H, d, J = 12.9 Hz), 2.52-2.77 (7 H, m), 3.10-3.27 (4 H, m), 6.81-6.94 (2H, m), 7.06-7.17 (2H, m).

Reference Example 295
Preparation of (S) -1- (2-Methyl-2-oxiranylmethyl) piperidine-4-carboxylic acid ethyl ester (R) -Toluene-4-sulfonic acid (2-methyl-2-oxiranylmethyl) A mixture of ester (13.5 g, 55.8 mmol), piperidine 4-carboxylic acid ethyl ester (8.9 g, 50.9 mmol) and triethylamine (6.5 g, 64.4 mmol) in DMF (70 ml) Stir at room temperature for 2 days. The reaction solution was poured into water and extracted with ethyl acetate. The organic phase was washed with water and brine, dried over magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (n-hexane / ethyl acetate = 3/1) to give (S) -1- (2-methyl-2-oxiranylmethyl) piperidine-4-carboxylic acid as a colorless oily substance Ethyl ester (5.4 g, 47% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.25 (3 H, t, J = 7.1 Hz), 1.36 (3 H, s), 1.67-1.93 (4 H, m), 1.97-2.08 (2 H, m), 2.19-2.37 (2H, m), 2.48 (1H, d, J = 11.5 Hz), 2.58 (2H, s), 2.78-2.97 (2H, m), 4.13 (2H, q, J = 7.1 Hz).

  The compounds of Reference Example 296 to Reference Example 299 were produced in the same manner as in Reference Example 295, using the corresponding starting materials.

Reference Example 296
(S) -1- (2-Methyl-2-oxiranylmethyl) piperidine-4-carboxylic acid 4-trifluoromethylbenzyl ester colorless oil, 18% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
1.35 (3 H, s), 1.69-2. 10 (6 H, m), 2. 25-2. 37 (1 H, m), 2. 28 (1 H, d, J = 12.9 Hz), 2.48 (1 H, d, J = 12.9 Hz), 2.58 (2 H, s), 2.81-3.00 (2 H, m), 5.11 (2 H, s), 7.20 ( 2H, d, J = 8.0 Hz), 7.38 (2H, d, J = 8.0 Hz).

Reference Example 297
(S) -1- (2-Methyl-2-oxiranylmethyl) piperidine-4-carboxylic acid 4-chlorobenzyl ester colorless oil, yield 26%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.36 (3 H, s), 1.75-2.16 (7 H, m), 2.27 (1 H, d, J = 12.9 Hz), 2.50 (1 H, d, J = 12.9 Hz ), 2.58 (2H, s), 2.87-3.09 (2H, m), 5.13 (2H, s), 7.17-7.21 (2H, m), 7.27- 7.31 (2H, m).

Reference Example 298
(S) -1- (2-Methyl-2-oxiranylmethyl) piperidine-4-carboxylic acid (4-chlorobenzyl) amide colorless oil, yield 26%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.36 (3 H, s), 1.75-2.16 (7 H, m), 2.27 (1 H, d, J = 12.9 Hz), 2.50 (1 H, d, J = 12.9 Hz ), 2.58 (2H, s), 2.87-3.09 (2H, m), 4.41 (2H, d, J = 5.8 Hz), 5.78 (1 H, br), 7. 17-7. 21 (2 H, m), 7. 27-7. 31 (2 H, m).

Reference Example 299
(S) -1- (2-Methyl-2-oxiranylmethyl) piperidine-4-carboxylic acid (4-chlorophenyl) amide colorless oil, yield 33%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.37 (3 H, s), 1.82-2.08 (6 H, m), 2.13-2.27 (1 H, m), 2. 30 (1 H, d, J = 13.0 Hz), 2.53 (1 H, d, J = 13.0 Hz), 2.60 (2 H, s), 2.93-3.12 (2 H, m), 7.16 (1 H, bs), 7.26 7.31 (2H, m), 7.45-7.49 (2H, m).

Reference Example 300
Preparation of 5- (2-Methyl-2-oxiranylmethylsulfanyl) -1-phenyl-1H-tetrazole 1-phenyl-5-mercapto-1H-tetrazole (3.5 g, 19.64 mmol), toluene-4 Sulfonic acid (2-methyl-2-oxiranylmethyl) ester (5 g, 20.64 mmol), potassium carbonate (3 g, 21.71 mmol), sodium iodide (4.5 g, 30.02 mmol) and The mixture of DMF (30 ml) was stirred at 60 ° C. for 6 hours. The reaction solution was cooled to room temperature, water was added, and the mixture was extracted twice with ethyl acetate. The organic phases were combined, washed with 5% caustic soda, washed three times with water and dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (n-hexane / ethyl acetate = 2/1) to give 5- (2-methyl-2-oxiranylmethylsulfanyl) -1-phenyl-1H-tetrazole (1 of colorless oil) .9 g, yield 39%) were obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.46 (3H, s), 2.73 (1H, d, J = 4.5 Hz), 2.91 (1 H, d, J = 4.5 Hz), 3.61 (1 H, d, J = 13) .9 Hz), 3.77 (1 H, d, J = 13.9 Hz), 7.50-7.65 (5 H, m).

Reference Example 301
Preparation of 3- (2-methyl-2-oxiranyl) propionic acid tert-butyl ester Trimethylsulfoxonium under ice cooling with sodium hydride (3.71 g, 92.82 mmol) in DMSO (50 ml) suspension Add iodide (19.54 g, 88.78 mmol) and stir for 2.5 hours, then add a solution of 4-oxo-pentanoic acid tert-butyl ester (13.90 g, 80.71 mmol) in DMSO (20 ml) Add and stir at room temperature for 15 hours. The mixture was poured into ice water, extracted with diethyl ether, washed with water, dried over magnesium sulfate and concentrated under reduced pressure. A slightly yellow liquid of 3- (2-methyl-2-oxiranyl) propionic acid tert-butyl ester (10.1 g, yield 67%) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.32 (3 H, s), 1.44 (9 H, s), 1.85 to 1.94 (2 H, m), 2.27 to 2. 33 (2 H, m), 2.58 (1 H, 1 H, d, J = 4.7 Hz), 2.63 (1 H, d, J = 4.7 Hz).

Reference Example 302
Preparation of 2-isopropyl-2-methoxymethoxymethyloxirane m-chloroperbenzoic acid (213 g, 861 mmol) in a solution of 2-methoxymethoxymethyl-3-methyl-1-butene (89 g, 615 mmol) in methylene chloride (800 ml) The reaction mixture was added little by little under ice cooling and stirred for 18 hours at room temperature, then washed with 10% aqueous potassium sulfite solution and aqueous sodium hydrogencarbonate solution, dried over sodium sulfate and concentrated under reduced pressure to give 2-isopropyl-2-colorless liquid Methoxy methoxymethyl oxirane (98 g, quantitative) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
0.95 (3 H, d, J = 7.0 Hz), 1.02 (3 H, d, J = 7.0 Hz), 1.84-2.05 (1 H, m), 2.66 (1 H, d , J = 4.9 Hz), 2.75 (1 H, d, J = 4.9 Hz), 3.37 (3 H, s), 3.63 (1 H, d, J = 11.3 Hz), 3.70 (1 H, d, J = 11.3 Hz), 4.62 (2 H, s).

Reference Example 303
Preparation of 2-ethyl-2-methoxymethoxymethyloxirane To a solution of 2-methoxymethoxymethyl-1-butene (98 g, 757 mmol) prepared in Reference Example 206 in methylene chloride (800 ml), m-chloroperbenzoic acid (143. 7 g (833 mmol) was added little by little under ice-cooling and stirring under room temperature, stirred at room temperature overnight, washed with water, 10% aqueous sodium sulfite solution, aqueous sodium hydrogen carbonate solution, dried over sodium sulfate and concentrated under reduced pressure to give colorless liquid 2 -Ethyl 2-methoxymethoxymethyloxirane (111 g, quantitative) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
0.96 (3 H, t, J = 7.5 Hz), 1.60-1.73 (1 H, m), 1.77-1.93 (1 H, m), 2. 66 (1 H, d, J = 4.8 Hz), 2.74 (1 H, d, J = 4.8 Hz), 3.37 (3 H, s), 3.56 (1 H, d, J = 11.2 Hz), 3.65 (1 H) , D, J = 11.2 Hz), 4.64 (2 H, s).

Reference Example 304
Preparation of 2- (2-methoxymethoxyethyl) oxirane m-chloroperbenzoic acid (20.6 g, 95) in a solution of 4-methoxymethoxy-1-butene (10.46 g, 90.1 mmol) in methylene chloride (250 ml) .6 mmol) was added little by little under ice-cooling and stirring for 6 hours at room temperature, the reaction solution was filtered and the filtrate was washed with 10% aqueous sodium sulfite solution and aqueous sodium hydrogencarbonate solution, dried over magnesium sulfate and concentrated under reduced pressure The colorless liquid 2- (2-methoxymethoxyethyl) oxirane (10.3 g, 86%) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.69-1.96 (2H, m), 2.53 (1H, dd, J = 2.7 Hz, 4.9 Hz), 2.79 (1 H, t, J = 4.9 Hz), 3.02 -3.08 (1 H, m), 3.38 (3 H, s), 3.68 (2 H, t, J = 5.9 Hz), 4.64 (2 H, s).

Reference Example 305
Preparation of 4- (4-Trifluoromethylphenoxy) piperidine-1-Carbonyl Chloride Triphosgene in a suspension of 4- (4-trifluoromethylphenoxy) piperidine (0.6 g, 2.45 mmol) in toluene (6 ml) 0.25 g (0.86 mmol) and pyridine (0.4 ml, 4.90 mmol) were added and heated to reflux for 2.5 hours. Ethyl acetate is added, and the mixture is washed with 10% hydrochloric acid, dried over magnesium sulfate, concentrated under reduced pressure, and slightly yellow liquid 4- (4-trifluoromethylphenoxy) piperidine-1-carbonyl chloride (0.72 g, yield 96) %) Got.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.79-2.10 (4H, m), 3.50-3.96 (4H, m), 4.58-4. 75 (1H, m), 6.97 (2H, d, J = 8 .8 Hz), 7.56 (2 H, d, J = 8.8 Hz).

Reference Example 306
Preparation of 4- (4-trifluoromethylphenylamino) piperidine-1-carbonyl chloride Triphosgene (0 ml) of (4-trifluoromethylphenylamino) piperidine (1.14 g, 4.67 mmol) in methylene chloride (10 ml) .55 g (1.87 mmol) and triethylamine (0.98 ml, 7.01 mmol) were added and stirred at room temperature for 1.5 hours. The reaction solution was washed with water, dried over magnesium sulfate and concentrated under reduced pressure to give 4- (4-trifluoromethylphenylamino) piperidine-1-carbonyl chloride (1.43 g, quantitative) as a pale yellow liquid .
¹ H-NMR (CDCl ₃ ) δ ppm:
1.33-1.65 (2H, m), 2.09-2.24 (2H, m), 3.02-3.22 (1 H, m), 3.22-3.41 (1 H, m) ), 3.48-3.70 (1 H, m), 4. 20-4. 35 (2 H, m), 6. 66 (2 H, d, J = 8.5 Hz), 7.43 (2 H, d) , J = 8.5 Hz).

  As shown in Reference Example 305 or Reference Example 306, the compounds of Reference Examples 307 to 324 are produced by reacting amines, cyclic amines, and benzene-fused heterocyclic compounds in the presence of triphosgene and triethylamine or pyridine. did.

Reference Example 307
5-chloro-2,3-dihydroindole-1-carbonyl chloride slightly yellow solid, yield 100%
¹ H-NMR (CDCl ₃ ) δ ppm:
3.19 (2 H, t, J = 8.3 Hz), 4. 28 (2 H, t, J = 8.3 Hz), 7.18-7.22 (2 H, m), 7. 80 (1 H, d , J = 9.5 Hz).

Reference Example 308
6-Chloro-3,4-dihydro-1H-isoquinoline-2-carbonyl chloride slightly yellow liquid, yield 100%
¹ H-NMR (CDCl ₃ ) δ ppm:
2.83-3.00 (2H, m), 3.83 (1H, t, J = 6.0 Hz), 3.90 (1 H, t, J = 6.0 Hz), 4.71 (1 H, s) 4.80 (1 H, s), 7.06 (1 H, d, J = 8.0 Hz), 7.13-7.28 (2 H, m).

Reference Example 309
6-Chloro-3,4-dihydro-2H-quinoline-1-carbonyl chloride yellow liquid, yield 100%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.99-2.09 (2H, m), 2.79 (2H, t, J = 6.5 Hz), 3.94 (2 H, t, J = 6.3 Hz), 7.14-7.20 (2H, m), 7.62 (1 H, d, J = 8.5 Hz).

Reference Example 310
5-chloro-1,3-dihydroisoindole-2-carbonyl chloride yellow liquid, yield 100%,
¹ H-NMR (CDCl ₃ ) δ ppm:
3.19 (2 H, t, J = 8.3 Hz), 4. 28 (2 H, t, J = 8.3 Hz), 7.18-7.22 (2 H, m), 7. 80 (1 H, d , J = 9.5 Hz).

Reference Example 311
4-Chlorocarbonylpiperazine-1-carboxylic acid tert-butyl ester slightly yellow solid, 100% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
1.47 (9H, s), 3.16-3.29 (2H, m), 3.37-3.55 (4H, m), 3.55-3.78 (2H, m).

Reference Example 312
4- (4-Trifluoromethoxybenzyloxycarbonyl) piperazine-1-carbonyl chloride 100% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
3.43-3.80 (8H, m), 5.15 (2H, s), 7.15-7.25 (2H, m), 7.33-7.45 (2H, m).

Reference Example 313
4- [3- (4-Trifluoromethylphenyl) -2-propenyloxycarbonyl] piperazine-1-carbonyl chloride 100% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
3.54-3.65 (4H, m), 3.65-3.72 (2H, m), 3.72-3.83 (2H, m), 4.80 (2H, dd, J = 1 .1 Hz, 6.1 Hz), 6.39 (1 H, dt, J = 6.1 Hz, 15.9 Hz), 6.68 (1 H, d, J = 15.9 Hz), 7.49 (2 H, d, J = 8.4 Hz), 7.59 (2 H, d, J = 8.4 Hz).

Reference Example 314
4- (4-Chlorobenzyl) piperazine-1-carbonyl chloride brown liquid, yield 100%
¹ H-NMR (CDCl ₃ ) δ ppm:
2.65-2.96 (4H, m), 3.67-4.08 (6H, m), 7.36-7.39 (4H, m).

Reference Example 315
4- (4-Trifluoromethylbenzyl) piperazine-1-carbonyl chloride brown liquid, yield 100%
¹ H-NMR (CDCl ₃ ) δ ppm:
2.97-3.12 (4H, m), 3.91-4.06 (2H, m), 4.06-4.21 (2H, m), 4.15 (2H, s), 7.. 58-7.73 (4H, m).

Reference Example 316
4- (4-Trifluoromethoxybenzyl) piperazine-1-carbonyl chloride brown liquid, yield 100%
¹ H-NMR (CDCl ₃ ) δ ppm:
2.58-2.85 (4H, m), 3.58-3. 90 (6H, m), 7.17-7. 25 (2H, m), 7.35-7. 46 (2H, m) ).

Reference Example 317
4- (4-Trifluoromethoxyphenyl) -1,2,3,6-tetrahydropyridine-1-carbonyl chloride slightly brown liquid, yield 57%
¹ H-NMR (CDCl ₃ ) δ ppm:
2.54-2.67 (2H, m), 3.85 (1H, t, J = 5.7 Hz), 3.94 (1 H, t, J = 5.7 Hz), 4.28 (1 H, d) , J = 2.7 Hz), 4.36 (1 H, d, J = 2.7 Hz), 5.94-6.06 (1 H, m), 7.16-7.21 (2 H, m), 7 36-7.41 (2H, m).

Reference Example 318
4- (4-Methoxyphenyl) -1,2,3,6-tetrahydropyridine-1-carbonyl chloride slightly brown liquid, yield 60%
¹ H-NMR (CDCl ₃ ) δ ppm:
2.54-2.67 (2H, m), 3.51 (1H, t, J = 5.6 Hz), 3.81 (3H, s), 3.92-4.02 (1 H, m), 4.23-4.31 (1H, m), 4.34-4.37 (1H, m), 5.87-5.96 (1H, m), 6.85-6.90 (2H, m) ), 7.29-7.35 (2H, m).

Reference Example 319
4- (3-trifluoromethylphenyl) -1,2,3,6-tetrahydropyridine-1-carbonyl chloride slightly brown liquid, yield 100%
¹ H-NMR (CDCl ₃ ) δ ppm:
2.58-2.71 (2H, m), 3.87 (1H, t, J = 5.7 Hz), 3.96 (1 H, t, J = 5.7 Hz), 4.31 (1 H, d) , J = 2.8 Hz), 4.39 (1 H, d, J = 2.8 Hz), 6.04-6.15 (1 H, m), 7.45-7.63 (4 H, m).

Reference Example 320
4- (4-Bromophenyl) -1,2,3,6-tetrahydropyridine-1-carbonyl chloride slightly brown liquid, yield 100%
¹ H-NMR (CDCl ₃ ) δ ppm:
2.52-2.67 (2H, m), 3.84 (1H, t, J = 5.7 Hz), 3.93 (1 H, t, J = 5.7 Hz), 4.27 (1 H, d) , J = 2.6 Hz), 4.35 (1 H, d, J = 2.6 Hz), 5.94-6.06 (1 H, m), 7.21-7.24 (2 H, m), 7 43-7.49 (2H, m).

Reference Example 321
4- (4-Fluorophenyl) -1,2,3,6-tetrahydropyridine-1-carbonyl chloride slightly brown liquid, yield 100%
¹ H-NMR (CDCl ₃ ) δ ppm:
2.54-2.67 (2H, m), 3.84 (1 H, t, J = 5.7 Hz), 3.93 (1 H, t, J = 5.7 Hz), 4.27 (1 H, d) , J = 2.6 Hz), 4.35 (1 H, d, J = 2.6 Hz), 5.90-6.00 (1 H, m), 7.00-7.07 (2 H, m), 7 24-7.35 (2H, m).

Reference Example 322
N- (4-Chlorophenyl) -N-cyclohexylcarbamyl chloride slightly yellow solid, yield 100%
¹ H-NMR (CDCl ₃ ) δ ppm:
0.79 to 1.06 (1 H, m), 1.14 (2 H, t, J = 3, 5 Hz, 12.5 Hz), 1.23 to 1.44 (2 H, m), 1.50 to 65 (1H, m), 1.67-1.81 (2H, m), 1.87-2.00 (2H, m), 4.78 (1H, m), 7.06-7. 10 (2H , M), 7.36-7.41 (2H, m).

Reference Example 323
N-Methyl-N- (4-trifluoromethoxybenzyl) carbamyl chloride yellow liquid, yield 100%
¹ H-NMR (CDCl ₃ ) δ ppm:
3.09 (3 H, s), 4.58 (2 H, s), 7.16-7.33 (4 H, m).

Reference Example 324
4-[(4-Trifluoromethylbenzylidene) amino] piperazine-1-carbonyl chloride brown liquid, yield 100%
¹ H-NMR (CDCl ₃ ) δ ppm:
3.17-3.39 (4H, m), 3.74-4.02 (4H, m), 7.56 (1 H, s), 7.60 (2 H, d, J = 8.3 Hz), 7.69 (2H, d, J = 8.3 Hz).

Reference Example 325
Preparation of 4- (4-trifluoromethoxyphenyl) piperazine-1-carbonyl chloride Ice-cold suspension of 1- (4-trifluoromethoxyphenyl) piperazine (1.0 g, 4.1 mmol) in toluene (20 ml) While stirring, triphosgene (0.42 g, 1.4 mmol) and pyridine (0.66 ml, 8.2 mmol) were added and stirred at 100 ° C. for 4.5 hours. Ethyl acetate was added, washed with water, dried over magnesium sulfate and concentrated under reduced pressure to give 4- (4-trifluoromethoxyphenyl) piperazine-1-carbonyl chloride (1.3 g, quantitative) as a brown liquid .
¹ H-NMR (CDCl ₃ ) δ ppm:
3.08-3.30 (4H, m), 3.67-4.00 (4H, m), 6.79-6.98 (2H, m), 7.08-7. 17 (2H, m) ).

  The compounds of Reference Example 326 to Reference Example 332 were quantitatively produced in the same manner as in Reference Example 325 using the corresponding starting materials.

Reference Example 326
4- (4-Trifluoromethylphenyl) piperazine-1-carbonyl chloride
¹ H-NMR (CDCl ₃ ) δ ppm:
3.26-3.39 (4H, m), 3.76-3.87 (2H, m), 3.87-3.98 (2H, m), 6.87-6.98 (2H, m) ), 7.48-7.59 (2H, m).

Reference Example 327
4- (4-Methoxyphenyl) piperazine-1-carbonyl chloride
¹ H-NMR (CDCl ₃ ) δ ppm:
3.04-3.15 (4H, m), 3.52-3.75 (2H, m), 3.75-3.92 (2H, m), 3.78 (3H, s), 6. 81-6.98 (4H, m).

Reference Example 328
4- (4-Chlorophenyl) piperazine-1-carbonyl chloride
¹ H-NMR (CDCl ₃ ) δ ppm:
3.10-3.25 (4H, m), 3.37-3.52 (2H, m), 3.73-3.90 (2H, m), 6.83-6.88 (2H, m) ), 7.20-7.25 (2H, m).

Reference Example 329
4- (3-Chlorophenyl) piperazine-1-carbonyl chloride
¹ H-NMR (CDCl ₃ ) δ ppm:
3.15 to 3.29 (4H, m), 3.73 to 3.94 (4H, m), 6.77 to 6.81 (1H, m), 6.88 to 6.91 (2H, m) ), 7.20 (1 H, t, J = 8.3 Hz).

Reference Example 330
4- (3,4-Dichlorophenyl) piperazine-1-carbonyl chloride
¹ H-NMR (CDCl ₃ ) δ ppm:
3.08-3.27 (4H, m), 3.37-3.48 (2H, m), 3.60-3.73 (1 H, m), 3.73-3.90 (1 H, m) ), 6.75 (1 H, dd, J = 2.9 Hz, 9.0 Hz), 6.96-6.98 (1 H, m), 7.30 (1 H, dd, J = 5.1 Hz, 9. 0 Hz).

Reference Example 331
4- (4-Fluorophenyl) piperazine-1-carbonyl chloride
¹ H-NMR (CDCl ₃ ) δ ppm:
3.04-3.19 (4H, m), 3.40-3.50 (2H, m), 3.62-3.75 (1H, m), 3.75-3.92 (1H, m) ), 6.86-7.03 (4H, m).

Reference Example 332
4- (3-Trifluoromethylphenyl) piperazine-1-carbonyl chloride
¹ H-NMR (CDCl ₃ ) δ ppm:
3.21-3.35 (4H, m), 3.42-3.54 (2H, m), 3.77-3.96 (2H, m), 7.02-7.19 (3H, m) ), 7.31 to 7.46 (1 H, m).

Reference Example 333
Preparation of 4- [1- (4-trifluoromethoxyphenyl) piperidin-4-yl] piperazine-1-carboxylic acid tert-butyl ester 4-piperidin-4-ylpiperazine-1-carboxylic acid tert-butyl ester (1 .5 g, 5.67 mmol), 4- (trifluoromethoxy) bromobenzene (3.36 g, 13.92 mmol), palladium acetate (25 mg, 0.11 mmol), BINAP (87 mg, 0.14 mmol), A mixture of tert-butoxy sodium (1.07 g, 11.14 mmol) and toluene (20 ml) was stirred at 80 ° C. for 8 hours under a nitrogen atmosphere. The reaction solution is cooled to room temperature, 10 ml of ethyl acetate and 20 ml of saturated brine are added, and the mixture is filtered. The filtrate is separated and the organic phase is dried over sodium sulphate. After filtering the organic phase, the filtrate is concentrated, and the residue is purified by silica gel column chromatography (methylene chloride / methanol = 20/1) to give 4- [1- (4-trifluoromethoxyphenyl) piperidine as a yellow powder. -4-yl] piperazine-1-carboxylic acid tert-butyl ester (1.01 g, 42%) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.49 (9H, s), 1.52-1.75 (2H, m), 1.83-1.99 (2H, m), 2.31-2.52 (5H, m), 64- 2.81 (2H, m), 3.36-3.49 (4H, m), 3.62-3.75 (2H, m), 6.86 (2H, d, J = 8.5 Hz ), 7.09 (2H, d, J = 8.5 Hz).

Reference Example 334
Preparation of 1- [1- (4-trifluoromethoxyphenyl) piperidin-4-yl] piperazine tert-butyl 4- [1- (4-trifluoromethoxyphenyl) piperidin-4-yl] piperazine-1-carboxylate The ester (1 g, 2.33 mmol) was dissolved in methylene chloride (10 ml), trifluoroacetic acid (10 ml) was added under ice-cooling, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was washed successively with 25% sodium hydroxide (40 ml) and saturated brine (10 ml) and dried over sodium sulfate. The reaction mixture was filtered and the filtrate was concentrated to give yellow amorphous 1- [1- (4-trifluoromethoxyphenyl) piperidin-4-yl] piperazine (770 mg, quantitative).
¹ H-NMR (CDCl ₃ ) δ ppm:
1.52-1.75 (2H, m), 1.83-1.99 (2H, m), 2.25-2.38 (1H, m), 2.48-2.76 (6H, m) ), 2.79-2.99 (4H, m), 3.56-3.75 (2H, m), 6.89 (2H, d, J = 8.5 Hz), 7.09 (2H, d) , J = 8.5 Hz).

  The compounds shown in the following Tables 1 to 6 were produced in the same manner as in Reference Example 334. In Tables 1 and 2, "none" in the column of X means that X is a direct bond. Also, in Table 3 and later, "Ph" means a phenyl group or a phenylene group.

  The compounds shown in the following Table 7 were produced in the same manner as in Reference Example 222.

  The compounds of Reference Example 372 to Reference Example 395 were produced in the same manner as in Reference Example 186.

Reference Example 372
1- (4-hydroxyphenyl) -4-phenylpiperidin-4-ol Ms; 269 (M ^<+> ).

Reference Example 373
4- (4-Chlorophenyl) -1- (4-hydroxyphenyl) piperidin-4-ol Ms; 349 (M ⁺ -1).

Reference Example 374
1- (4-Hydroxyphenyl) -4- (4-trifluoromethoxyphenyl) piperidin-4-ol Ms: 353 (M ⁺ ).

Reference Example 375
(4-hydroxyphenyl)-[4- (4-trifluoromethoxyphenoxy) piperidin-1-yl] methanone Ms; 381 (M ⁺ ).

Reference Example 376
1- (4-hydroxyphenyl) piperidine-4-carboxylic acid tert-butyl ester
¹ H-NMR (CDCl ₃ ) δ ppm;
1.46 (9 H, s), 1.76-2.05 (4 H, m), 2.22-2.34 (1 H, m), 2.62-2.73 (2 H, m), 3. 39-3.48 (2H, m), 4.39-4. 49 (1H, m), 4.78 (1H, s), 6.72-6.78 (2H, m), 6.82- 6.89 (2H, m).

Reference Example 377
4- (4-phenylpiperidin-1-yl) phenol Ms: 253 (M ⁺ ).

Reference Example 378
4- (4,4-Diethoxypiperidin-1-yl) phenol Ms: 265 (M ⁺ ).

Reference Example 379
2-Dimethylaminomethyl-4- [4- (4-trifluoromethoxyphenoxy) piperidin-1-yl] phenol Ms: 410 (M ⁺ ).

Reference Example 380
4- (4- [1,3] dioxolan-2-ylpiperidin-1-yl) phenol
¹ H-NMR (CDCl ₃ ) δ ppm;
1.51 to 1.70 (2H, m), 1.80 to 1.92 (2H, m), 2.53 to 2.66 (2H, m), 3.48 to 3.57 (2H, m) ), 3.84-3.92 (2H, m), 3.92-4.02 (2H, m), 4.63 (1 H, brs), 4.69 (1 H, d, J = 4.9 Hz) 6.70-6.78 (2H, m), 6.83-6.91 (2H, m).

Reference Example 381
4- [4- (4-Trifluoromethoxyphenyl) piperazin-1-yl] phenol Ms: 337 (M ⁺ ).

Reference Example 382
4- (4-hydroxyphenoxy) piperidine-1-carboxylic acid tert-butyl ester Ms: 293 (M ⁺ ).

Reference Example 383
4- [1- (4-Trifluoromethylphenyl) piperidin-4-yloxy] phenol Ms; 337 (M ⁺ ).

Reference Example 384
4- (1,4-dioxa-8-azaspiro [4,5] -decane-8-yl) phenol
¹ H-NMR (CDCl ₃ ) δ ppm;
1.87 (4H, t, J = 5.7 Hz), 3.18 (4 H, t, J = 5.7 Hz), 3.99 (4 H, s), 6.74 (2 H, d, J = 8 .9 Hz), 6.88 (2 H, d, J = 8.9 Hz).

Reference Example 385
4- (4-phenyl-1,2,3,6-tetrahydropyridin-1-yl) phenol Ms: 251 (M ⁺ ).

Reference Example 386
4- (4-hydroxyphenyl) piperazine-1-carboxylic acid tert-butyl ester
¹ H-NMR (CDCl ₃ ) δ ppm;
1.49 (9H, s), 2.95 to 3.00 (4H, m), 3.55 to 3.60 (4H, m), 5.77 (1H, s), 6.74-6. 86 (4H, m).

Reference Example 387
4- [4- (4-Trifluoromethoxyphenyl) piperazin-1-yl] phenol
¹ H-NMR (CDCl ₃ ) δ ppm;
3.19-3.24 (4H, m), 3.29-3.34 (4H, m), 4.51 (1 H, s), 6.76-6.82 (2 H, m), 6. 87-6.97 (4H, m), 7.11-7.16 (2H, m).

Reference Example 388
4- {4-[(4-Trifluoromethoxybenzylidene) amino] piperazin-1-yl} phenol Ms: 349 (M ⁺ -1).

Reference Example 389
4- [4- (4-Chlorobenzyl) piperazin-1-yl] phenol
¹ H-NMR (CDCl ₃ ) δ ppm;
2.60 (4H, t, J = 4.8 Hz), 3.08 (4 H, t, J = 4.8 Hz), 3.53 (2 H, s), 6.71-6.78 (2 H, m) ), 6.81 to 6.89 (2H, m), 7.27 to 7.42 (4H, m).

Reference Example 390
3- (4-hydroxyphenyl) oxazolidin-2-one
¹ H-NMR (CDCl ₃ ) δ ppm;
3.94-4.01 (2H, m), 4.35-4.42 (2H, m), 6.73-6.80 (2H, m), 7.29-7.36 (2H, m) ), 9.34 (1 H, s).

Reference Example 391
4- (4-pyridyl) phenol
¹ H-NMR (CDCl ₃ ) δ ppm;
6.87-6.93 (2H, m), 7.60-7. 70 (4H, m), 8.54-8.57 (2H, m), 9.85 (1 H, s).

Reference Example 392
4-hydroxy-N- (4-trifluoromethoxyphenyl) benzamide
¹ H-NMR (CDCl ₃ ) δ ppm;
6.84-6.87 (2H, m), 7.31-7.34 (2H, m), 7.83-7.87 (4H, m), 10. 11 (1H, brs), 10. 15 (1 H, brs).

Reference Example 393
(4-hydroxyphenyl)-(4-trifluoromethoxyphenyl) methanone
¹ H-NMR (CDCl ₃ ) δ ppm;
6.08 (1H, s), 6.92-6.96 (2H, m), 7.30-7.33 (2H, m), 7.76-7.83 (4H, m).

Reference Example 394
(4-hydroxyphenyl)-(4-trifluoromethylphenyl) methanone Ms: 266 (M ⁺ ).

Reference Example 395
4- (4-Trifluoromethoxyphenoxy) phenol
¹ H-NMR (CDCl ₃ ) δ ppm;
4.67 (1H, brs), 6.81-6.85 (2H, m), 6.90-6.96 (4H, m), 7.13-7.16 (2H, m).

  The compounds shown in the following Tables 8 to 12 were produced in the same manner as in Reference Example 186.

Example 1
Preparation of 2-chloro-1- (3-chloro-2-hydroxypropyl) -4-nitroimidazole 2-Chloro-4-nitro-1H-imidazole (2 g, 13.56 mmol) and epichlorohydrin (1. Sodium bicarbonate (1.25 g, 14.91 mmol) was added to a solution of 38 g (14.91 mmol) in acetonitrile (60 ml), and the mixture was heated to reflux for 4 hours. The reaction solution was returned to room temperature and concentrated under reduced pressure. To the residue was added water (20 ml), extracted twice with methylene chloride (15 ml), the extract was dried over sodium sulfate and filtered. The filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (ethyl acetate / n-hexane = 1/1) to give 2-chloro-1- (3-chloro-) as a slightly yellow oil. 2-hydroxypropyl) -4-nitroimidazole (2.04 g, 63% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
3.51-3.70 (2H, m), 4.02-4. 35 (4H, m), 7.92 (1 H, s).

Example 2
Preparation of 2-chloro-4-nitro-1- (2-oxiranylmethyl) imidazole 2-Chloro-1- (3-chloro-2-hydroxypropyl) -4-nitroimidazole (2) prepared in Example 1 Dissolve .04 g (8.5 mmol) in methylene chloride (20 ml) and add 1,8-diazabicyclo [5.4.0] -7-undecene (DBU, 2.04 ml, 13.67 mmol) at room temperature Stir overnight. The reaction mixture was washed successively with 3N hydrochloric acid (20 ml) and saturated brine (20 ml), dried over sodium sulfate and filtered. The filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 20/1) to give 2-chloro-4-nitro-1- (2-oxira) as a colorless oil. Nilmethyl) imidazole (190 mg, 11% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
2.55 to 2.69 (1 H, m), 2.97 (1 H, t, J = 4.2 Hz), 3.26 to 3.43 (1 H, m), 3.94 (1 H, dd, J = 6.4 Hz, 15.0 Hz), 4.52 (1 H, dd, J = 2.6 Hz, 15.0 Hz), 7.88 (1 H, s).

Example 3
Preparation of 2-Chloro-1- (2,3-dihydroxy-2-methylpropyl) -4-nitroimidazole 2-Chloro-4-nitro-1H-imidazole (6.78 g, 46 mmol) and 4-nitrobenzoic acid 2-Methyl-2-oxiranylmethyl ester (12 g, 51 mmol) was dissolved in ethyl acetate (24 ml), triethylamine (1.3 ml, 9.2 mmol) was added to this solution and heated to reflux for 14 hours. The reaction solution was concentrated under reduced pressure, and methylene chloride (40 ml) was added to the residue for crystallization. The resulting crystals were collected by filtration and dissolved in methanol (120 ml). Potassium carbonate (318 mg, 2.3 mmol) was added and stirred at room temperature for 1 hour. Under ice-cooling, 6N hydrochloric acid (0.8 ml) and magnesium sulfate (8 g) were added in this order and stirred for 30 minutes. The insolubles were removed by filtration through Celite, and the filtrate was concentrated under reduced pressure. To the residue were added ethyl acetate (6 ml) and toluene (60 ml). The resulting crystals are collected by filtration and dried at 50 ° C. to give 2-chloro-1- (2,3-dihydroxy-2-methylpropyl) -4-nitroimidazole (7.88 g) as white powder crystals. Rate of 72%).
¹ H-NMR (DMSO-d ₆ ) δ ppm:
1.02 (3 H, s), 3. 25 (2 H, d, J = 5.3 Hz), 4.04 (2 H, s), 4.98 (1 H, s), 5. 10 (1 H, t, J = 5.4 Hz), 8.29 (1 H, s).

Example 4
Preparation of 2-Chloro-1- (2-hydroxy-3-methanesulfonyloxy-2-methylpropyl) -4-nitroimidazole 2-Chloro-1- (2,3-dihydroxy-2-one) prepared in Example 3 To a solution of methylpropyl) -4-nitroimidazole (5.05 g, 21.43 mmol) in pyridine (10 ml) was added methanesulfonyl chloride (2.01 ml, 25.72 mmol) with stirring under ice cooling, and 1 at room temperature. Stir for .5 hours. The reaction mixture was added with 6N hydrochloric acid, extracted with ethyl acetate, dried over magnesium sulfate and concentrated under reduced pressure to give 2-chloro-1- (2-hydroxy-3-methanesulfonyloxy-2-methylpropyl) -4-nitro as a yellow oil. Imidazole (6.72 g, quantitative) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.31 (3H, s), 2.10 (1 H, s), 3.11 (3 H, s), 4.08-4. 23 (4 H, m), 8.02 (1 H, s).

Example 5
Preparation of 2-Chloro-1- [2-hydroxy-2-methyl-3- (4-methylbenzenesulfonyloxy) propyl] -4-nitroimidazole 2-Chloro-4-nitro-1H-imidazole (1 g, 6. 78 mmol) and a mixture of para-toluenesulfonic acid 2-methyl-2-oxiranyl methyl ester (2.46 g, 10.15 mmol), benzyltriethylammonium chloride (150 mg, 0.66 mmol) and acetonitrile (10 ml) Heated to reflux for 8 hours. The reaction solution is cooled to room temperature, diluted with ethyl acetate, washed twice with saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 6/1) to give 2-chloro-1- [2-hydroxy-2-methyl-3 as a slightly yellow oil. There was obtained-(4-methylbenzenesulfonyloxy) propyl] -4-nitroimidazole (1.86 g, 70% yield).
¹ H-NMR (CDCl ₃ ) δ ppm:
1.25 (3 H, s), 2.46 (3 H, s), 2. 80 (1 H, s), 3.9 1 (1 H, d, J = 10.4 Hz), 3.95 (1 H, d, J) J = 10.4 Hz), 4.04-4.16 (2 H, m), 7. 38 (2 H, d, J = 8.0 Hz), 7.76 (2 H, d, J = 8.0 Hz), 7.93 (1 H, s).

Example 6
Preparation of 2-Chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitroimidazole 2-Chloro-1- (2-hydroxy-3-methanesulfonyloxy-2-) prepared in Example 4 Methylpropyl) -4-nitroimidazole (6.72 g, 21.43 mmol) is treated in the same manner as in Example 2 to give 2-chloro-1- (2-methyl-2-oxiranyl) as white powdery crystals. Methyl) -4-nitroimidazole (5.6 g, 94% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.39 (3H, s), 2.62 (2H, d, J = 4.0 Hz), 2.78 (1 H, d, J = 4.0 Hz), 4.00 (1 H, d, J = 14 .9 Hz), 4.38 (1 H, d, J = 14.9 Hz), 7.87 (1 H, s).

Example 7
Preparation of 2-chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitro-1H-imidazole 2-Chloro-1- [2-hydroxy-2-methyl-3 prepared in Example 5 By the same method as in Example 2 using (4-methylbenzenesulfonyloxy) propyl] -4-nitroimidazole (1.11 g, 2.84 mmol), 2-chloro-1- (slightly yellow powder crystal) 2-Methyl-2-oxiranylmethyl) -4-nitroimidazole (523 mg, 85% yield) was obtained.

  Physical properties of the obtained compound were the same as those of the compound obtained in Example 6.

Example 8
Preparation of (R) -2-Chloro-1- [2-hydroxy-3- (4-methylbenzenesulfonyloxy) propyl] -4-nitroimidazole 2-Chloro-4-nitro-1H-imidazole (10 g, 67. 79 mmol) and (R)-(-)-glycidyl tosylate (17.02 g, 74.58 mmol) are dissolved in acetonitrile (50 ml) and sodium hydrogen carbonate (6.26 g, 74.15 mmol) is added to this solution Was added and heated to reflux for 3.5 hours. The reaction solution was allowed to cool to room temperature, and after filtration, the filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (ethyl acetate / n-hexane = 1/2) to give (R) -2-chloro-1- [2-hydroxy-3- (4-) as a slightly yellow oil. Methylbenzenesulfonyloxy) propyl] -4-nitroimidazole (16.9 g, yield 66%) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
2.47 (3 H, s), 3. 65 (1 H, d, J = 5.8 Hz), 3.93-4. 33 (5 H, m), 7.38 (2 H, d, J = 8.3 Hz ), 7.70 (2H, d, J = 8.3 Hz), 7.86 (1 H, s).

Example 9
Preparation of (R) -2-Chloro-4-nitro-1- (2-oxiranylmethyl) imidazole 2-Chloro-4-nitro-1H-imidazole (1 g, 6.78 mmol) and (R)-( -)-Glycidyl tosylate (1.7 g, 7.45 mmol) was dissolved in tetrahydrofuran (THF) (10 ml) and sodium hydrogen carbonate (600 mg, 7.14 mmol) was added to this solution and heated to reflux for 11 hours . The reaction mixture was concentrated under reduced pressure, water was added, and the mixture was extracted with ethyl acetate. The organic phase was washed successively with water and brine, dried over sodium sulfate and filtered. The filtrate is concentrated, and the residue is purified by silica gel column chromatography (ethyl acetate / n-hexane = 1/1) to give (R) -2-chloro-4-nitro-1- (2) as a slightly yellow oil. -Oxiranylmethyl) imidazole (1.45 g, 57% yield) was obtained.
Optical purity 79.2% ee
[Α] _D ²⁷ = 42.55 ° (concentration: 1.262, CHCl ₃ )
¹ H-NMR (CDCl ₃ ) δ ppm:
2.61 (1 H, t, J = 2.5 Hz, 4.3 Hz), 2.97 (1 H, t, J = 4.3 Hz), 3.25-3.34 (1 H, m,) 3. 95 (1 H, dd, J = 6.4 Hz, 15.0 Hz), 4.51 (1 H, dd, J = 2.6 Hz, 15.0 Hz), 7.88 (1 H, s).

Example 10
Preparation of (R) -2-Chloro-1- (2,3-dihydroxy-2-methylpropyl) -4-nitroimidazole 2-Chloro-4-nitro-1H-imidazole (600 g, 4.07 moles) and ( R) 4-Nitrobenzoic acid 2-methyl-2-oxiranyl methyl ester (1060 g, 4.47 mol) is dissolved in ethyl acetate (2124 ml) and to this solution triethylamine (113.64 ml, 0.82 mol) ) Was added and heated to reflux for 16 hours. The reaction solution was concentrated under reduced pressure, and ethyl acetate (530 ml) and toluene (5300 ml) were added to the residue to crystallize. The resulting crystals were collected by filtration and dissolved in methanol (10.6 l). After adding potassium carbonate (55.4 g, 0.4 mol) to this solution and stirring at room temperature for 1 hour, concentrated hydrochloric acid (66 ml) and magnesium sulfate (671 g) were added in this order under ice-cooling and stirred for 30 minutes . The insolubles were filtered through celite, and the filtrate was concentrated under reduced pressure. To the residue were added ethyl acetate (530 ml) and toluene (5300 ml). The obtained crystals are collected by filtration, dried at 50 ° C., and (R) -2-chloro-1- (2,3-dihydroxy-2-methylpropyl) -4-nitroimidazole (light tea powder crystals). 879.1 g (yield 92%) were obtained.
Optical purity 99.0% ee
[Α] _D ²⁷ = 17.38 ° (concentration: 1.03, DMSO)
¹ H-NMR (DMSO-d ₆ ) δ ppm:
1.01 (3 H, s), 3. 25 (2 H, d, J = 5.3 Hz), 4.05 (2 H, s), 5.01 (1 H, s), 5.11 (1 H, t, J = 5.4 Hz), 8.32 (1 H, s).

Example 11
Preparation of (R) -2-Chloro-1- (2-hydroxy-3-methanesulfonyloxy-2-methylpropyl) -4-nitroimidazole The (R) -2-chloro-1- (prepared according to Example 10) 2,3-Dihydroxy-2-methylpropyl) -4-nitroimidazole (879 g, 3.73 moles) was dissolved in pyridine (1778 ml) and cooled to 5 ° C. Methanesulfonyl chloride (432.7 ml, 5.59 mol) was gradually added dropwise to this at 15 ° C. or lower, and the mixture was stirred at the same temperature for 1 hour. To this was added 6N hydrochloric acid (5500 ml) at 30 ° C. or less, and stirred for 40 minutes under ice cooling. The precipitated crystals were collected by filtration and washed sequentially with water and toluene to obtain primary crystals. The filtrate was extracted twice with ethyl acetate (5 liters), the extract was washed with water, dried over magnesium sulfate, filtered, the filtrate was concentrated under reduced pressure, and the crystals obtained by adding toluene were collected by filtration. , Got secondary crystals. The primary and secondary crystals are combined, dried at 60 ° C., and (R) -2-chloro-1- (2-hydroxy-3-methanesulfonyloxy-2-methylpropyl) -4- 4 Nitroimidazole (942.6 g, 81% yield) was obtained.
¹ H-NMR (DMSO-d ₆ ) δ ppm:
1.12 (3 H, s), 3.23 (3 H, s), 4.09 (2 H, s), 4. 13 (2 H, s), 5. 60 (1 H, br), 8.34 (1 H) , S).

Example 12
Preparation of (R) -2-Chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitroimidazole (R) -2-Chloro-1- (2-hydroxy-) prepared in Example 11 3-Methanesulfonyloxy-2-methylpropyl) -4-nitroimidazole (942.6 g, 3 mol) is suspended in ethyl acetate (9426 ml), to which DBU (494 ml, 3.3 mol) is added, and it is at room temperature. Stir for 1 hour. The reaction was washed with water (5 liters). The aqueous layer was extracted twice with ethyl acetate (5 liters). The extract and the organic phase were combined, washed with saturated brine (5 liters), dried over magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (ethyl acetate / n-hexane = 1/2) to give (R) -2-chloro-1- (2-methyl-2) as white powder crystals. -Oxiranylmethyl) -4-nitroimidazole (600.7 g, 92% yield) was obtained.
Optical purity 98.8% ee
[Α] _D ²⁶ = 31.11 ° (concentration: 2.02, CHCl ₃ )
¹ H-NMR (CDCl ₃ ) δ ppm:
1.38 (3 H, s), 2.62 (1 H, d, J = 4.0 Hz), 2.78 (1 H, d, J = 4.0 Hz), 4.00 (1 H, d, J = 14 .9 Hz), 4.38 (1 H, d, J = 14.9 Hz), 7.87 (1 H, s).

Example 13
Preparation of (R) -2-Chloro-1- [2-hydroxy-2-methyl-3- (4-methylbenzenesulfonyloxy) propyl] -4-nitroimidazole 2-Chloro-4-nitro-1H-imidazole ( 18.4 g (125 mmol) and (R) -4-methylbenzenesulfonic acid 2-methyl-2-oxiranyl methyl ester (36.2 g, 149 mmol) were suspended in acetonitrile (150 ml), to which benzyltriethyl was added. Ammonium chloride (5.7 g, 25 mmol) was added and heated to reflux for 8 hours. The reaction solution was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 20/1) to give white amorphous (R) -2-chloro-1- [2-hydroxy-2-methyl-3- (4-methylbenzene) Sulfonyloxy) propyl] -4-nitroimidazole (20.1 g, 43%) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.24 (3 H, s), 2.47 (3 H, s), 2.8 1 (1 H, s), 3. 90 (1 H, d, J = 10.4 Hz), 3.95 (1 H, d, J = 10.4 Hz), 4.04-4.14 (2 H, m), 7. 39 (2 H, d, J = 8.0 Hz), 7.76 (2 H, d, J = 8.0 Hz), 7.91 (1 H, s).

Example 14
Preparation of (R) -2-Chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitroimidazole (Another synthesis method of the compound of Example 12)
15. 2-chloro-4-nitro-1H-imidazole (1.51 g, 10.17 mmol) and (R) -4-methylbenzenesulfonic acid 2-methyl-2-oxiranylmethyl ester (3.70 g, 15. 25 mmol) was suspended in acetonitrile (15 ml), to which benzyltriethylammonium chloride (0.23, 1.02 mmol) was added, and the mixture was heated to reflux for 10 hours. The reaction solution is cooled to room temperature, ethyl acetate is added, and the mixture is washed with an aqueous sodium hydrogen carbonate solution, dried over magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure and dissolved in ethyl acetate (40 ml). Under ice cooling and stirring, DBU (1.57 ml, 10.17 mmol) was added, and the mixture was further stirred at room temperature for 1.5 hours. The reaction solution was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (n-hexane / ethyl acetate = 7/3) to give (R) -2-chloro-1- (2-methyl-2-oxiranylmethyl) as a slightly yellow oil. -4-Nitroimidazole (1.50 g, 68% yield) was obtained.

Example 15
Preparation of (S) -2-Chloro-4-nitro-1- [2-hydroxy-3- (4-nitrobenzoyloxy) -2-methylpropyl] imidazole 2-Chloro-4-nitro-1H-imidazole (3 g) 20.34 mmol) and (S) -4-nitrobenzoic acid 2-methyl-2-oxiranyl methyl ester (5.31 g, 22.37 mmol) are dissolved in ethyl acetate (10 ml) and Triethylamine (0.57 ml, 4.07 mmol) was added and stirred at 60-65 ° C. for 10 hours. The reaction solution was concentrated under reduced pressure. Ethyl acetate (3 ml) and toluene (30 ml) were added to the residue, and the resulting crystals were collected by filtration to give (S) -2-chloro-4-nitro-1- [2-hydroxy-3- as yellow powder crystals. (4-Nitrobenzoyloxy) -2-methylpropyl] imidazole (6.82 g, 87% yield) was obtained.
¹ H-NMR (DMSO-d ₆ ) δ ppm:
1.23 (3H, s), 4.11-4.33 (4H, m), 5.61 (1H, s), 8. 25 (2H, d, J = 8.9 Hz), 8.31- 8.45 (3H, m).

Example 16
Preparation of (S) -2-Chloro-1- (2,3-dihydroxy-2-methylpropyl) -4-nitroimidazole (S) -2-Chloro-4-nitro-1- [5 prepared in Example 15 Dissolve 2-hydroxy-3- (4-nitrobenzoyloxy) -2-methylpropyl] imidazole (6.8 g, 17.67 mmol) in methanol (68 ml) and potassium carbonate (122 mg, 0.88 mmol) In addition, it stirred at room temperature overnight. After ice cooling, 6N hydrochloric acid (0.3 ml) and magnesium sulfate (3 g) were added in this order and stirred for 30 minutes. The insolubles were filtered through celite, and the filtrate was concentrated under reduced pressure. Ethyl acetate (3.4 ml) and toluene (34 ml) were added to the residue, and the resulting crystals were collected by filtration to give (S) -2-chloro-1- (2,3-dihydroxy-2-methyl) as yellow powder crystals. Propyl) -4-nitroimidazole (4.09 g, 97% yield) was obtained.
¹ H-NMR (DMSO-d ₆ ) δ ppm:
1.02 (3 H, s), 3. 25 (2 H, d, J = 5.3 Hz), 4.05 (2 H, s), 4.98 (1 H, s), 5.11 (1 H, t, J = 5.2 Hz), 8.30 (1 H, s).

Example 17
Preparation of (S) -2-Chloro-1- (2-hydroxy-2-methyl-3-methanesulfonyloxypropyl) -4-nitroimidazole The (S) -2-chloro-1- (prepared in Example 16) 2,3-Dihydroxy-2-methylpropyl) -4-nitroimidazole (4.05 g, 16.9 mmol) was dissolved in pyridine (8 ml) and cooled to 4 ° C. Methanesulfonyl chloride (1.6 ml, 20.28 mmol) was gradually added dropwise at 15 ° C. or less, and the mixture was further stirred at the same temperature for 1 hour. 6 N hydrochloric acid (33 ml) was added dropwise at 30 ° C. or less. The reaction mixture was extracted three times with methylene chloride (20 ml), the organic phases were combined, washed with water (20 ml) and saturated brine (20 ml), dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. Toluene (10 ml) is added to the residue, and the resulting crystals are collected by filtration to give (S) -2-chloro-1- (2-hydroxy-2-methyl-3-methanesulfonyloxypropyl)-in the form of white powdery crystals. 4-Nitroimidazole (3.04 g, 57% yield) was obtained.
¹ H-NMR (DMSO-d ₆ ) δ ppm:
1.12 (3 H, s), 3. 24 (3 H, s), 4.09 (2 H, s), 4. 13 (2 H, s), 5.62 (1 H, br), 8.34 (1 H) , S).

Example 18
Preparation of (S) -2-Chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitroimidazole (S) -2-Chloro-1- (2-hydroxy-) prepared in Example 17 Dissolve 2-methyl-3-methanesulfonyloxypropyl) -4-nitroimidazole (3.02 g, 9.51 mmol) in methylene chloride (30 ml) and add DBU (1.7 ml, 11.41 mmol), The mixture was stirred at room temperature for 1.5 hours. The reaction solution was washed successively with 30 ml of 3 N hydrochloric acid and 20 ml of saturated brine, dried over magnesium sulfate and filtered. The filtrate is concentrated, and the residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 20/1) to give (S) -2-chloro-1- (2-methyl-2-oxy) as a slightly yellow oil. Ranylmethyl) -4-nitroimidazole (1.89 g, 91% yield) was obtained.
Optical purity 93.2% ee
[Α] _D ²⁷ = -29.15 ° (concentration: 1.18, CHCl ₃ )
¹ H-NMR (CDCl ₃ ) δ ppm:
1.39 (3H, s), 2.63 (1 H, d, J = 4.0 Hz), 2.79 (1 H, d, J = 4.0 Hz), 4.00 (1 H, d, J = 14 .9 Hz), 4.38 (1 H, d, J = 14.9 Hz), 7.88 (1 H, s).

Example 19
Preparation of 2-tert-butoxymethyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole 2,4-dinitro-1H-imidazole (10 g, 63.3 mmol), 2-tert-butoxy Methyl oxirane (27 ml, 189 mmol) and sodium acetate (5.19 g, 189 mmol) were suspended in ethanol (100 ml) and the suspension was heated to reflux for 17 hours. The reaction solution was returned to room temperature and concentrated under reduced pressure. To the residue was added water, extracted with methylene chloride, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / methanol = 50/1) to give 2-tert-butoxymethyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole as white powder crystals. (3.2 g, 21% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.18 (9 H, s), 3.63-3.80 (2 H, m), 4.22-4. 36 (2 H, m), 5. 27-5. 42 (1 H, m), 7. 53 (1 H, s).

  Example 20, analogously to Example 19, using 2-methyl-2- (2-methoxymethoxyethyl) oxirane, 2-ethyl-2-methoxymethoxymethyloxirane or 2-isopropyl-2-methoxymethoxymethyloxirane The compound of Example 22 was made.

Example 20
2- (2-Methoxymethoxyethyl) -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole white powder crystal, yield 48%, MS = 257.

Example 21
2-ethyl-2-methoxymethoxymethyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole slightly yellow powder crystal, yield 49%
¹ H-NMR (DMSO-d ₆ ) δ ppm:
0.91 (3 H, t, J = 7.5 Hz), 1.91 (2 H, q, J = 7.5 Hz), 3.24 (3 H, s), 3.72 (1 H, d, J = 11) .2 Hz), 3.78 (1 H, d, J = 11.2 Hz), 4.15 (1 H, d, J = 11.2 Hz), 4.23 (1 H, d, J = 11.2 Hz), 4 .59 (2H, s), 8.10 (1 H, s).

Example 22
2-isopropyl-2-methoxymethoxymethyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole slightly yellow powder crystal, yield 90%
¹ H-NMR (DMSO-d ₆ ) δ ppm:
0.94 (6H, d, J = 6.9 Hz), 2.16-2.32 (1 H, m), 3.24 (3 H, s), 3.76 (1 H, d, J = 13.0 Hz) ), 3.82 (1 H, d, J = 13.0 Hz), 4.18 (1 H, d, J = 13.0 Hz), 4.25 (1 H, d, J = 13.0 Hz), 4.59 (2H, s), 8.09 (1 H, s).

Example 23
Preparation of 2-Chloro-1- (2-hydroxy-4-methoxymethoxybutyl) -4-nitroimidazole 2-Chloro-4-nitro-1H-imidazole (5.74 g, 38.93 mmol) in ethanol (60 ml) Sodium acetate (3.51 g, 42.82 mmol) and 2- (2-methoxymethoxyethyl) oxirane (10.3 g, 77.86 mmol) were added to the solution, and the mixture was heated to reflux for 13.5 hours. Ethanol was distilled off under reduced pressure, water was added to the residue, and extracted with methylene chloride. After drying over magnesium sulfate and concentration under reduced pressure, the residue was purified by silica gel column chromatography (methylene chloride / methanol = 100/1). Crystallization with methylene chloride and diisopropyl ether gave 2-chloro-1- (2-hydroxy-4-methoxymethoxybutyl) -4-nitroimidazole (8.51 g, yield 78%) as pale yellow powder crystals .
¹ H-NMR (CDCl ₃ ) δ ppm:
1.67 (2H, m), 3.38 (3H, s), 3.46 (1 H, d, J = 2.4 Hz), 3.78-3.83 (2 H, m), 4.00 ( 1 H, dd, J = 7.6 Hz, 14.3 Hz), 4.11-4.21 (2 H, m), 4.63 (2 H, s), 7.96 (1 H, s).

  The compound of Example 24 was produced in the same manner as Example 23 using 2-methyl-2-methoxymethoxymethyloxirane.

Example 24
2-Chloro-1- (2-hydroxy-3-methoxymethoxypropyl) -4-nitroimidazole colorless liquid, yield 63%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.20 (3H, s), 3.08 (1H, s), 3.42 (3H, s), 3.53 (2H, q, J = 10.4 Hz, 13.8 Hz), 4.67 ( 2H, s), 8.01 (1 H, s).

Example 25
Preparation of 2- (2-Methoxymethoxyethyl) -6-nitro-2,3-dihydroimidazo [2,1-b] oxazole 2-Chloro-1- (2-hydroxy-4-methoxy prepared in Example 23 To a solution of methoxy) butyl-4-nitroimidazole (8.45 g, 30.21 mmol) in 1,4-dioxane (100 ml) was added sodium hydride (1.33 g, 33.23 mmol) under ice-cooling and stirring. Heated to reflux for 40 hours. The reaction mixture was concentrated under reduced pressure, ice-cooled, water was added to the residue, and the mixture was extracted with methylene chloride. The extract is dried over magnesium sulfate and concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (methylene chloride / methanol = 100/1), crystallized with methylene chloride and diisopropyl ether, 2- (2 -Methoxy methoxyethyl) -6-nitro-2,3-dihydroimidazo [2,1-b] oxazole (3.41 g, yield 47%) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
2.11-2.35 (2H, m), 3.36 (3H, s), 3.75 (2H, dd, J = 4.8 Hz, 6.8 Hz), 4.08 (1 H, dd, J = 7.6 Hz, 10.3 Hz), 4.40 (1 H, dd, J = 7.6 Hz, 10.3 Hz), 4.61 (2 H, s), 5.43-5.54 (1 H, m) , 7.53 (1 H, s).

  The compound of Example 26 was produced in the same manner as in Example 25 using the 2-chloro-1- (2-hydroxy-3-methoxymethoxypropyl) -4-nitroimidazole produced in Example 24.

Example 26
2-methoxymethoxymethyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole slightly yellow powder crystal, yield 38%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.66 (3 H, s), 3.34 (3 H, s), 3.63 (1 H, d, J = 11.0 Hz), 3.84 (1 H, d, J = 11.0 Hz), 93 (1 H, d, J = 9.9 Hz), 4.37 (1 H, d, J = 9.9 Hz), 4.62 (2 H, s), 7.52 (1 H, s).

Example 27
Preparation of (R) -2-Chloro-1- (2-hydroxy-3-methoxymethoxy-2-methylpropyl) -4-nitroimidazole The (R) -2-chloro-1- (2) prepared in Example 10 , 3-Dihydroxy-2-methylpropyl) -4-nitroimidazole (7.4 g, 31 mmol) is suspended in methylene chloride (120 ml), to which N-ethyldiisopropylamine (13.1 ml, 74 mmol) and chloro Methyl methyl ether (7.1 ml, 74 mmol) was added and stirred at room temperature for 46 hours. The reaction solution was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 9/1) to obtain a slightly yellow liquid (R) -2-chloro-1- (2-hydroxy-3-methoxymethoxy-2-methylpropyl) ) -4-Nitroimidazole (6.0 g, 69% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.20 (3 H, s), 3.08 (1 H, s), 3.42 (3 H, s), 3.50 (1 H, d, J = 10.4 Hz), 3.55 (1 H, d, J = 10.4 Hz), 4.05 (1 H, d, J = 14.4 Hz), 4.15 (1 H, d, J = 14.4 Hz), 4.67 (2 H, s), 8.01 (1 H) 1 H, s).

Example 28
Preparation of (R) -2-Methoxymethoxymethyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole (R) -2-Chloro-1-one prepared in Example 27 Sodium hydride (1.0 g, 25 mmol) in a solution of (2-hydroxy-3-methoxymethoxy-2-methylpropyl) -4-nitroimidazole (6.0 g, 21 mmol) in DMF (30 ml) under ice-cooling and stirring ) Was added and stirred at room temperature for 1.5 hours. Ice water is added to the reaction solution, and the precipitate is collected by filtration, washed with water, and (R) -2-methoxymethoxymethyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,2] as a yellow solid. 1-b] oxazole (3.1 g, 59% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.66 (3 H, s), 3.34 (3 H, s), 3.63 (1 H, d, J = 11.0 Hz), 3.84 (1 H, d, J = 11.0 Hz), 93 (1 H, d, J = 10.0 Hz), 4.42 (1 H, d, J = 10.0 Hz), 4.63 (2 H, s), 7.52 (1 H, s).

Example 29
Preparation of 2-chloro-1- (5-acetoxy-2-hydroxy-2-methylpentyl) -4-nitroimidazole 2-chloro-4-nitro-1H-imidazole (6.8 g, 43 mmol), 2- (2-) 3-acetoxypropyl) -2-methyloxirane (5.8 g, 39.3 mmol) and sodium acetate (3.9 g, 47.6 mmol) are suspended in ethanol (60 ml) and this suspension is heated to reflux overnight did. The reaction solution was returned to room temperature and concentrated under reduced pressure. Water was added to the residue and extracted twice with methylene chloride. The organic phases were combined, washed successively with saturated aqueous sodium bicarbonate solution and saturated brine, dried over sodium sulfate and filtered. The filtrate is concentrated under reduced pressure to give light tea oil 2-chloro-1- (5-acetoxy-2-hydroxy-2-methylpentyl) -4-nitroimidazole (9.5 g, yield 79%) Obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.21 (3 H, s), 1.50 to 1.81 (4 H, m), 2.05 (3 H, s), 3.9 1 to 4. 12 (4 H, m), 8.02 (1 H, 1 H, s).

Example 30
Preparation of 2- (3-Acetoxypropyl) -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole 2-Chloro-1- (5-acetoxy-) prepared in Example 29 Using 2-hydroxy-2-methylpentyl) -4-nitroimidazole (9.5 g, 31.1 mmol) and according to a method similar to Example 25, 2- (3-acetoxy) propyl-2 as a slightly orange powder -Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole (5.2 g, yield 62%) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.67 (3H, s), 1.67-2.00 (4H, m), 2.05 (3H, s), 3.91-4.14 (4H, m), 7.52 (1H, 1H, s) s).

Example 31
Preparation of 2- (2-Hydroxyethyl) -6-nitro-2,3-dihydroimidazo [2,1-b] oxazole 2- (2-methoxymethoxyethyl) -6-nitro-2 prepared in Example 25 Trifluoroacetic acid (2 ml) was added to a solution of 3, 3-dihydroimidazo [2,1-b] oxazole (0.2 g, 0.822 mmol) in methylene chloride (10 ml), and the mixture was further stirred overnight at room temperature. After concentration under reduced pressure, the residue is purified by silica gel column chromatography (methylene chloride / methanol = 100/1), crystallized with methanol and diisopropyl ether, and 2- (2-hydroxyethyl) -6-nitro as pale yellow powdery crystals. There was obtained -2,3-dihydroimidazo [2,1-b] oxazole (0.11 g, yield 65%).
¹ H-NMR (DMSO-d ₆ ) δ ppm:
1.92-2.14 (2H, m), 3.52-3.63 (2H, m), 4.05 (1H, dd, J = 7.6 Hz, 10.6 Hz), 4.43 (1 H , Dd, J = 7.6 Hz, 10.6 Hz), 4.72 (1 H, t, J = 2.7 Hz), 5.38-5. 53 (1 H, m), 8.12 (1 H, s) .

Example 32
Preparation of 2-hydroxymethyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole 2-tert-butoxymethyl-6-nitro-2,3-dihydroimidazo [2 prepared in Example 19 The reaction is carried out in the same manner as in Example 31 using 1,1-b] oxazole (5.82 g, 24.1 mmol) to give 2-hydroxymethyl-6-nitro-2,3-dihydroimidazo [2] as white powder crystals. , 1-b] oxazole (4.25 g, 95% yield) was obtained.
¹ H-NMR (DMSO-d ₆ ) δ ppm:
3.55-3.67 (1 H, m), 3.72-3.88 (1 H, m), 4.12 (1 H, dd, J = 6.5 Hz, 10.5 Hz), 4.36 (1 H) , T, J = 10.4 Hz), 5.25-5.50 (2 H, m), 8.11 (1 H, s).

Example 33
Preparation of 2-hydroxymethyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole 2-methoxymethoxymethyl-2-methyl-6-nitro-2 prepared in Example 26 The reaction is carried out in the same manner as in Example 31 using 2,3-dihydroimidazo [2,1-b] oxazole (4.14 g, 38 mmol), and 2-hydroxymethyl-2-methyl-6- in the form of slightly yellow powdery crystals. Nitro-2,3-dihydroimidazo [2,1-b] oxazole (2.17 g, 64% yield) was obtained.
Melting point 166-168 ° C
¹ H-NMR (DMSO-d ₆ ) δ ppm:
1.51 (3 H, s), 3.53 (1 H, d, J = 12.1 Hz), 3.64 (1 H, d, J = 12.1 Hz), 4.03 (1 H, d, J = 10 .6 Hz), 4.24 (1 H, d, J = 10.6 Hz), 5.40 (1 H, br), 8. 10 (1 H, s).

Example 34
Preparation of 2- (2-Hydroxyethyl) -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole 2- (2-Methoxymethoxyethyl) -2 prepared in Example 20 The reaction is carried out in the same manner as in Example 31 using -methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole (13.4 g, 52.1 mmol). There was obtained-(2-hydroxyethyl) -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole (2, 32 g, yield 21%).
¹ H-NMR (DMSO-d ₆ ) δ ppm:
1.58 (3H, s), 1.93-2.17 (2H, m), 3.59 (2H, t, J = 6.4 Hz), 4.04 (1 H, d J = 10.9 Hz) , 4.33 (d, 1 H, J = 10.9 Hz), 8.11 (1 H, s).

Example 35
Preparation of 2-ethyl-2-hydroxymethyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole 2-ethyl-2-methoxymethoxymethyl-6-nitro-2 prepared in Example 21 3, 3-dihydroimidazo [2, 1-b] oxazole (21.5 g, 83.7 mmol) was suspended in methanol (430 ml), to which concentrated hydrochloric acid (2.15 ml) was added, and the mixture was heated to reflux for 5 hours. The reaction solution is concentrated under reduced pressure, and the precipitate is collected by filtration to give 2-ethyl-2-hydroxymethyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole (7. 14 g, 40% yield) were obtained.
¹ H-NMR (DMSO-d ₆ ) δ ppm:
0.89 (3 H, t, J = 7.4 Hz), 1.95 (2 H, q, J = 7.4 Hz), 3.53-3.69 (2 H, m), 4.08 (1 H, d , J = 10.8 Hz), 4.21 (1 H, d, J = 10.8 Hz), 5.39 (t, 1 H, J = 5.6 Hz), 8.09 (1 H, s).

  The compound of Example 36 was produced in the same manner as in Example 35 using the corresponding starting materials.

Example 36
2-hydroxymethyl-2-isopropyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole slightly yellow powder crystal, yield 50%
¹ H-NMR (DMSO-d ₆ ) δ ppm:
0.91 (6H, d, J = 6.9 Hz), 2.12-2.23 (1 H, m), 3.60-3.77 (2 H, m), 4. 16 (2 H, s), 5.35 (1 H, t, J = 5.6 Hz), 8.08 (1 H, s).

Example 37
Preparation of (R) -2-Hydroxymethyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole (R) -2-methoxymethoxymethyl-2 prepared in Example 28 Trifluoroacetic acid (15 ml) was added to a solution of -methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole (3.1 g, 13 mmol) in methylene chloride (30 ml), and further 25 at room temperature. Stir for hours. The reaction solution was concentrated under reduced pressure, methanol was added, and concentrated under reduced pressure. To the residue is added 2-propanol, and the precipitated crystals are collected by filtration, washed with 2-propanol and (R) -2-hydroxymethyl-2-methyl-6-nitro-2,3-dihydroimidazo of pale yellow powder crystals. [2,1-b] oxazole (1.2 g, 46% yield) was obtained.
Melting point 162-163 ° C
Optical purity 97% ee
[Α] _D ²⁶ = -19.01 ° (concentration: 0.526, DMSO).

Example 38
Preparation of 2-Methyl-2- (3-hydroxypropyl) -6-nitro-2,3-dihydroimidazo [2,1-b] oxazole 2- (3-Acetoxypropyl) -2- 2 prepared in Example 30 A mixture of methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole (3.2 g, 11.88 mmol), potassium carbonate (320 mg, 2.32 mmol) and methanol (35 ml) at room temperature The mixture was stirred for 2 hours. The reaction solution is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (methylene chloride / methanol = 25/1) to give a slightly yellow powder of 2-methyl-2- (3-hydroxypropyl) -6-. Nitro-2,3-dihydroimidazo [2,1-b] oxazole (2.1 g, 78%) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.67-1.72 (5 H, m), 1.91-2. 07 (2 H, m), 3.51-3. 65 (2 H, m), 4.01 (1 H, d, J = 10 .5 Hz), 4.15 (1 H, d, J = 10.5 Hz), 7.66 (1 H, s).

Example 39
Preparation of Methanesulfonic Acid 3- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-yl) propyl ester 2-Methyl-2- (prepared in Example 38) 3-hydroxypropyl) -6-nitro-2,3-dihydroimidazo [2,1-b] oxazole (2.1 g, 9.24 mmol), triethylamine (2.8 g, 20.09 mmol), 4-dimethyl A solution of methanesulfonyl chloride (1.4 ml, 18.09 mmol) in 10 ml of methylene chloride was slowly added dropwise to a mixture of aminopyridine (50 mg, 0.41 mmol) and methylene chloride (80 ml) under ice-cooling And stirred overnight at room temperature. The reaction solution was concentrated, 10% hydrochloric acid was added to the residue, and the mixture was stirred for 30 minutes under ice cooling. The precipitated crystals are collected by filtration and washed with water to give methanesulfonic acid 3- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-yl) propyl ester as white powder. (2.6 g, 92% yield) was obtained.
¹ H-NMR (DMSO-d ₆ ) δ ppm:
1.58 (3H, s), 1.65 to 2.02 (4H, m), 3.17 (3H, s), 4.05 to 4.26 (4H, m), 8.12 (1H, 1H) s).

  The compounds of Example 40 to Example 42 were produced in the same manner as in Example 39, using the corresponding starting materials.

Example 40
Methanesulfonic acid 6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-yl methyl ester slightly yellow powder, yield 82%
¹ H-NMR (DMSO-d ₆ ) δ ppm:
3.25 (3 H, s), 4.11 (1 H, dd, J = 6.6 Hz, 11.0 Hz), 4.47 (1 H, t, J = 9.1 Hz), 4.55-4.70 (2H, m), 5.60-5. 75 (1 H, m), 8. 14 (1 H, s).

Example 41
Methanesulfonic acid 2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl ester slightly yellow powder, yield 87%
¹ H-NMR (DMSO-d ₆ ) δ ppm:
1.64 (3H, s), 3.24 (3H, s), 4.17 (1 H, d, J = 11.2 Hz), 4.27 (1 H, d, J = 11.2 Hz), 4. 52 (2 H, br), 8. 14 (1 H, s).

Example 42
Methanesulfonic acid 2- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-yl) ethyl ester slightly yellow powder, yield 87%
¹ H-NMR (DMSO-d ₆ ) δ ppm:
1.61 (3H, s), 2.38 (2H, t, J = 6.5 Hz), 3.19 (3 H, s), 4.11 (1 H, d, J = 11.0 Hz), 4. 25 (1 H, d, J = 11.0 Hz), 4.36 (2 H, t, J = 6.5 Hz), 8.14 (1 H, s).

Example 43
Preparation of 5- (2-chloro-4-nitroimidazol-1-yl) -4-hydroxy-4-methylpentanoic acid tert-butyl ester 3- (2-Methyl-2-oxiranyl) propionic acid tert-butyl ester ( Sodium acetate (0.59 g, 7.18) in a suspension of 1.00 g (5.39 mmol) and 2-chloro-4-nitro-1H-imidazole (0.53 g, 3.59 mmol) in ethanol (5 ml) Add millimoles) and heat at reflux for 6 hours. The insolubles were filtered off and the filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / methanol = 100/1) to give 5- (2-chloro-4-nitroimidazol-1-yl) -4-hydroxy-4-methylpentane as a slightly yellow oil. Acid tert-butyl ester (0.94 g, 78% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.17 (3H, s), 1.45 (9 H, s), 1.78-1.87 (2 H, m), 2.43-2.54 (2 H, m), 3.59 (1 H, m) br), 3.99 (2H, s), 8.06 (1 H, s).

Example 44
Preparation of 3- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-yl) propionic acid tert-butyl ester 5- (2-Chloro) prepared in Example 43 -4-nitroimidazol-1-yl) -4-hydroxy-4-methylpentanoic acid tert-butyl ester (0.93 g, 2.79 mmol) in 1,4-dioxane (10 ml) with ice-cooling and stirring Sodium hydride (0.12 g, 3.07 mmol) was added and heated to reflux for 7.5 hours. The reaction mixture was concentrated under reduced pressure, water was added, extracted with methylene chloride, dried over magnesium sulfate and concentrated under reduced pressure. Wash with diethyl ether and white solid 3- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-yl) propionic acid tert-butyl ester (0.35 g, 42%).
¹ H-NMR (CDCl ₃ ) δ ppm:
1.45 (9 H, s), 1. 65 (3 H, s), 2.12-2.25 (2 H, m), 2.37-2.46 (2 H, m), 3.98 (1 H, 1 H, m) d, J = 10.3 Hz), 4.10 (1H, d, J = 10.3 Hz), 7.52 (1 H, s).

Example 45
Preparation of 3- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-yl) propionic acid 3- (2-Methyl-6-nitro prepared in Example 44 Trifluoroacetic acid (2 ml) in methylene chloride (14 ml) solution of -2,3-dihydroimidazo [2,1-b] oxazol-2-yl) propionic acid tert-butyl ester (0.72 g, 2.42 mmol) Was added and stirred for another 30 minutes at room temperature. The reaction solution is concentrated under reduced pressure and crystallized with ethanol and methylene chloride to give 3- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-yl) propion as a slightly yellow solid. The acid (0.30 g, 51%) was obtained.
¹ H-NMR (DMSO-d ₆ ) δ ppm:
1.32 (3H, s), 1.91-2.09 (1 H, m), 2.12-2.26 (1 H, m), 2.41-2.74 (2 H, m), 3. 89 (2 H, s), 7.96 (1 H, s), 12. 19 (1 H, br).

Example 46
Preparation of 2- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) benzoxazole 2-hydroxymethyl-2-methyl-6 prepared in Example 33 Sodium hydride (77 mg, 1.9 mmol) under ice-cooling and stirring in a solution of nitro-2,3-dihydroimidazo [2,1-b] oxazole (0.32 g, 1.6 mmol) in DMF (3 ml) Was added, and the mixture was further stirred at 0 ° C. for 30 minutes. A solution of 2-chlorobenzoxazole (0.30 g, 1.9 mmol) in DMF (3 ml) was added to the reaction solution with stirring under ice cooling, and the mixture was further stirred at room temperature for 44 hours. Ice water is added to the reaction mixture, and the mixture is extracted with ethyl acetate, washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / methanol = 100/1), recrystallized with acetonitrile and isopropanol, and lightly yellow solid 2- (2-methyl-6-nitro-2,3-dihydroimidazo [ 2,1-b] oxazol-2-ylmethoxy) benzoxazole (0.20 g, 39%) was obtained.
Mp 200-203 ° C.

Example 47
Preparation of (R) -2- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) benzoxazole (R) -2-prepared as in Example 37 Sodium hydride under ice-cooling and stirring in a solution of hydroxymethyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole (0.40 g, 2.0 mmol) in DMF (4 ml) (0.1 g, 2.4 mmol) was added and stirred at 0 ° C. for 30 minutes. A solution of 2-chlorobenzoxazole (0.38 g, 2.4 mmol) in DMF (4 ml) was added to the reaction solution with stirring under ice cooling, and the mixture was further stirred at room temperature for 48 hours. Ice water was added to the reaction solution, and the precipitate was collected by filtration and washed with water. Recrystallization from acetonitrile and isopropanol gives a pale yellow solid (R) -2- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) benzoxazole (0 .15 g (yield 24%) were obtained.
Melting point 232-233 ° C
Optical purity> 99.5% ee
^{_{[Α] D 26 = + 11.20}} ° ( concentration: 0.518, DMSO).

Example 48
Preparation of 2- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethylthio) benzoxazole 2-mercaptobenzoxazole (200 mg, 1.3 mmol) and DMF Sodium hydride (50 mg, 1.25 mmol) was added to the mixture of (3 ml) and stirred at room temperature for 1 hour. Next, to this reaction solution, methanesulfonic acid 2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl ester (330 mg, 1. 2 mmol) were added and stirred at 60-70 ° C. for 5 hours. The reaction solution was cooled to room temperature, water was added, and the mixture was extracted twice with ethyl acetate. The organic phases were combined, washed with 5% caustic soda, washed three times with water, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (n-hexane / ethyl acetate = 1/1) to give 2- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] as a white powder. Oxazol-2-ylmethylthio) benzoxazole (37 mg, 9% yield) was obtained.
Mp 163-166 ° C.

Example 49
Preparation of 2- [2- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-yl) ethylthio] benzoxazole Methanesulfonic acid 2--prepared according to Example 42 A white powder was obtained by the same method as in Example 48 using (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-yl) ethyl ester (300 mg, 1 mmol) Crystalline 2- [2- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-yl) ethylthio] benzoxazole (296 mg, yield 83%) was obtained .
Melting point 174-175 ° C.

Example 50
Preparation of 1- (2-chloro-4-nitroimidazol-1-yl) -2-methyl-3- (1-phenyl-1H-tetrazol-5-ylthio) propan-2-ol 2-chloro-4-nitro -1H-imidazole (1.2 g, 8.13 mmol), 5- (2-methyl-2-oxiranylmethylthio) -1-phenyl-1 H-tetrazole (1.9 g, 7.65 mmol), sodium acetate A mixture of (700 mg, 8.53 mmol) and ethanol (20 ml) was heated to reflux overnight. The reaction solution was returned to room temperature and concentrated under reduced pressure. To the residue was added water and extracted twice with ethyl acetate. The organic phases were combined, washed twice with saturated aqueous sodium bicarbonate solution, then sequentially washed with water and saturated brine, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / methanol = 50/1) to give 1- (2-chloro-4-nitroimidazol-1-yl) -2-methyl-3- (1-) as a slightly yellow powder. Phenyl-1 H-tetrazol-5-ylthio) propan-2-ol (2.1 g, 69% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.38 (3 H, s), 3.54 (1 H, d, J = 14.8 Hz), 3.62 (1 H, d, J = 14.8 Hz), 4.19 (2 H, s), 4. 58 (1 H, s), 7. 50-7. 67 (5 H, m), 8.08 (1 H, s).

Example 51
Preparation of 2-Methyl-6-nitro-2- (1-phenyl-1H-tetrazol-5-ylthiomethyl) -2,3-dihydroimidazo [2,1-b] oxazole 1- (2) prepared in Example 50 -Chloro-4-nitroimidazol-1-yl) -2-methyl-3- (1-phenyl-1H-tetrazol-5-ylthio) propan-2-ol (2.1 g, 5.3 mmol) and 1,1 Sodium hydride (220 mg, 5.5 mmol) was added to a mixture of 4-dioxane (40 ml) and heated to reflux for 24 hours. The reaction solution was returned to room temperature and concentrated under reduced pressure. To the residue was added water and extracted twice with ethyl acetate. The organic phases were combined, washed successively with water and saturated brine, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (n-hexane / ethyl acetate = 1/1), and light tea powdery 2-methyl-6-nitro-2- (1-phenyl-1H-tetrazol-5-ylthiomethyl)- 2,3-Dihydroimidazo [2,1-b] oxazole (500 mg, 26%) was obtained.
Melting point 140-147 [deg.] C.

Example 52
Preparation of (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxycarbonylamino) acetic acid tert-butyl ester Triphosgene (0.30 g, 0.76 mmol) A solution of glycine tert-butyl ester hydrochloride (0.52 g, 2.27 mmol) in methylene chloride (5 ml) and N-ethyldiisopropylamine (1.05 ml, 4.53) under ice-cooling and stirring in a solution of methylene chloride (10 ml) Then, the mixture was further stirred at room temperature for 2 hours. The insolubles were filtered off and the filtrate was concentrated under reduced pressure. This was prepared according to Example 33 2-hydroxymethyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole (0.30 g, 1.51 mmol) in DMF (3 ml) The solution was added with ice cooling and stirring, cuprous chloride (75 mg, 0.76 mmol) was further added, and the mixture was further stirred at room temperature for 22 hours. To the reaction solution was added water, and the mixture was extracted with ethyl acetate, washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (n-hexane / ethyl acetate = 3/2) to give (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole-2 as a white solid. -Ylmethoxycarbonylamino) acetic acid tert-butyl ester (40 mg, 7% yield) was obtained.
Melting point 104-106 [deg.] C.

Example 53
Preparation of (4-morpholinophenyl) carbamic acid 6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl ester 4-morpholinoaniline (0.40 g, 2.24 mmol) in THF To the (4 ml) solution was added 1,1′-carbonyldiimidazole (0.44 g, 2.69 mmol) under ice-cooling and stirring, and the mixture was stirred at 0 ° C. for 2 hours. The reaction mixture was filtered and washed with diethyl ether. The filtrate was ice cooled in a solution of 2-hydroxymethyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole (0.30 g, 1.62 mmol) prepared in Example 32 in DMF (3 ml). Under stirring, copper chloride (75 mg, 0.76 mmol) was further added, and the mixture was further stirred at room temperature for 2 hours. To the reaction solution was added water, and the mixture was extracted with ethyl acetate, washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / acetone = 9/1), washed with methylene chloride and ethyl acetate, and (4-morpholinophenyl) carbamic acid 6-nitro-2,3-dihydroimidazo as a white solid. [2,1-b] oxazol-2-ylmethyl ester (34 mg, 5% yield) was obtained.
¹ H-NMR (DMSO-d ₆ ) δ ppm:
2.93-3.09 (4H, m), 3.64-3.80 (4H, m), 4.13 (1 H, dd, J = 6.8 Hz, 10.9 Hz), 4.34-4 .55 (3 H, m), 5.55 to 5.73 (1 H, m), 6.77 to 6.95 (2 H, m), 7.18 to 7.41 (2 H, m), 8.15 (1 H, s), 9.52 (1 H, br).

Example 54
Preparation of 4-chlorophenylcarbamic acid 2- (6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-yl) ethyl ester 2-Hydroxyethyl-6-nitro-prepared in Example 31 A solution of 2,3-dihydroimidazo [2,1-b] oxazole (0.2 g, 1.0 mmol) in DMF (5 ml) under ice cooling with stirring, 4-chlorophenyl isocyanate (169 ml, 1.1 mmol) and chloride Copper (50 mg, 0.5 mmol) was added and stirred at room temperature for 4 hours. The mixture was ice-cooled, 10% hydrochloric acid was added, extraction was performed with ethyl acetate, the extract was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / methanol = 100/1), crystallized with methylene chloride and diisopropyl ether, and 4-chlorophenylcarbamic acid 2- (6-nitro-2,3-dihydroimidazo) as a white solid. [2,1-b] oxazol-2-yl) ethyl ester (0.16 g, 45% yield) was obtained.
¹ H-NMR (DMSO-d ₆ ) δ ppm:
2.16-2.38 (2H, m), 4.08 (1H, dd, J = 7.4 Hz, 10.6 Hz), 4.16-4.36 (2H, m), 4.47 (1H , Dd, J = 7.4 Hz, 10.6 Hz), 5.44-5.55 (1 H, m), 7. 30-7. 36 (2 H, m), 7.4 6-7.52 (2 H, 2 H, m) m), 8.14 (1 H, s), 9.83 (1 H, br).

  Phenyl isocyanate and 2-hydroxyethyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole, 2-ethyl-2-hydroxymethyl-6-nitro-2,3-dihydroimidazo Example 55 Analogously to Example 54 using [2, 1-b] oxazole or 2-hydroxymethyl-2-isopropyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole The compound of Example 57 is produced. In addition, with using 2-hydroxymethyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole and 3-fluorophenyl isocyanate or 4-tert-butoxycarbonylphenyl isocyanate, the procedure of The compounds of Example 58 and Example 59 were produced in the same manner.

Example 55
Phenylcarbamic acid 2- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-yl) ethyl ester yellow solid, 17% yield
¹ H-NMR (DMSO-d ₆ ) δ ppm:
1.63 (3H, s), 2.30 (2H, t, J = 6.9 Hz), 4.13 (1 H, d, J = 10.9 Hz), 4.21-4.32 (3 H, m) ), 6.96-7.02 (1 H, m), 7.24-7. 27 (2 H, m), 7.43-7.46 (2 H, m), 8.12 (1 H, s), 9.60 (1 H, br).

Example 56
Phenylcarbamic acid 2-ethyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl ester white solid, yield 60%
¹ H-NMR (DMSO-d ₆ ) δ ppm:
0.93 (3H, t, J = 7.4 Hz), 1.89-2.11 (2H, m), 4.19-4.29 (2H, m), 4.39-4. 50 (2H , M), 6.99 (1 H, t, J = 7.2 Hz), 7.23-7.29 (2 H, m), 7.34-7.55 (2 H, m), 8. 14 (1 H) , S), 9.70 (1 H, br).

Example 57
Phenylcarbamic acid 2-isopropyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl ester white solid, yield 73%
¹ H-NMR (DMSO-d ₆ ) δ ppm:
0.97 (6 H, dd, J = 2.7 Hz, 6.9 Hz), 2.25 to 2, 39 (1 H, m), 4.20 (1 H, d, J = 11.4 Hz), 4.30 (1 H, d, J = 11.4 Hz), 4.48 (2 H, s), 6.99 (1 H, t, J = 7.1 Hz), 7.23-7. 29 (2 H, m), 7 32-7.52 (2H, m), 8.13 (1 H, s), 9.67 (1 H, br).

Example 58
3-fluorophenylcarbamic acid 2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl ester white solid, yield 71%
Melting point 168-169 [deg.] C.

Example 59
4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxycarbonylamino) benzoic acid tert-butyl ester white solid, yield 32%
Melting point 177-178 [deg.] C.

Example 60
Preparation of 4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxycarbonylamino) benzoic acid 4- (2-Methyl-) prepared in Example 59 6-Nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxycarbonylamino) benzoic acid tert-butyl ester (185 mg, 0.44 mmol) in methylene chloride (10 ml) suspension Under ice-cooling and stirring, trifluoroacetic acid (1 ml) was added, and the mixture was further stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, dissolved in ethyl acetate, washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue is washed with ethyl acetate and white solid 4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxycarbonylamino) benzoic acid (50 mg, The yield was 31%).
Melting point 248 ° C (decomposition).

Example 61
Preparation of 4-chlorophenylcarbamic acid 2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl ester 4-chlorophenylcarbamic acid 2-methyl-2-oxiranylmethyl The ester (1.1 g, 4.4 mmol) and 2,4-dinitro-1H-imidazole (0.35 g, 2.2 mmol) are suspended in ethanol (1 ml) and stirred at room temperature for 24 hours, further sodium acetate (0.36 g, 4.4 mmol) and ethanol (2 ml) were added and heated to reflux for 6 hours. The reaction solution is concentrated under reduced pressure, water is added, and the mixture is extracted with ethyl acetate, dried over magnesium sulfate and concentrated under reduced pressure. Crystallization with methylene chloride and diethyl ether gives 4-chlorophenylcarbamic acid 2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl ester (0. 17 g (yield 22%) were obtained.
Melting point 179-181 [deg.] C.

Example 62
Preparation of N- (4-chlorophenyl) -N-methylcarbamic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester N- (4-chlorophenyl) -N- Methylcarbamic acid 2-methyl-2-oxiranyl methyl ester (1.7 g, 6.6 mmol) and 2-chloro-4-nitro-1H-imidazole (0.98 g, 6.6 mmol) in ethanol (10 ml) The mixture was suspended in water, sodium acetate (0.85 g, 10 mmol) was added, and the mixture was heated to reflux for 4 hours. Ethanol was distilled off under reduced pressure, saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with methylene chloride. The extract was dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 9/1) to give N- (4-chlorophenyl) -N-methylcarbamic acid 3- (2-chloro-4-nitroimidazole) as a slightly yellow oil. 1-yl) -2-hydroxy-2-methylpropyl ester (2.7 g, quantitative) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.15 (3H, br), 3.28 (3H, s), 3.78-4.28 (4H, m), 7.11-7.24 (2H, m), 7.30-7. 41 (2H, m), 7.90 (1 H, br).

Example 63
Preparation of N- (4-Chlorophenyl) -N-methylcarbamic acid 2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl ester N-prepared as described in Example 62 (4-Chlorophenyl) -N-methylcarbamic acid 3- (2-chloro-4-nitroimidazol-1yl) -2-hydroxy-2-methylpropyl ester (2.7 g, 6.6 mmol) in 1,4- Sodium hydride (0.32 g, 7.9 mmol) was added to a solution of dioxane (30 ml) under ice cooling with stirring, and the mixture was heated to reflux for 12 hours. The reaction solution is concentrated under reduced pressure, ice-cooled, and water is added. The mixture is extracted with methylene chloride, dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (ethyl acetate), crystallized with methylene chloride and ethanol, and white solid N- (4-chlorophenyl) -N-methylcarbamic acid 2-methyl-6-nitro-2,3-dihydro The imidazo [2,1-b] oxazol-2-ylmethyl ester (0.88 g, 36% yield) was obtained.
Melting point 146-148 [deg.] C.

Example 64
Preparation of (R) -4-chlorophenylcarbamic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester (R) -2-chloro prepared in Example 10 4-chlorophenyl isocyanate (1.3 g, 8. g) in a suspension of 1- (2,3-dihydroxy-2-methylpropyl) -4-nitroimidazole (1.5 g, 6.5 mmol) in THF (30 ml). A solution of 5 mmol) in THF (15 ml) and triethylamine (0.1 ml) were added, and the mixture was further stirred at room temperature for 19 hours. The insolubles are removed by filtration, the filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 9/1) to obtain (R) -4-chlorophenylcarbamic acid 3- (2-chloro) as a white solid. -4-Nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester (2.1 g, 83% yield) was obtained.
¹ H-NMR (DMSO-d ₆ ) δ ppm:
1.15 (3 H, s), 3.99 (2 H, s), 4.07 (2 H, s), 7. 29-7. 39 (2 H, m), 7. 45-7.5 8 (2 H, s) m), 8.33 (1 H, s), 9.86 (1 H, br).

  The compounds of Examples 65 to 69 were prepared in the same manner as Example 64, using various corresponding phenyl isocyanate compounds. The compounds of Example 70 and Example 71 were prepared in the same manner as Example 64 using benzyl isocyanate or methyl isocyanate.

Example 65
(R) -3-chlorophenylcarbamic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester yield 41%
¹ H-NMR (DMSO-d ₆ ) δ ppm:
1.15 (3 H, s), 4.00 (2 H, s), 4. 13 (2 H, s), 5.4 1 (1 H, s), 7.04-7.09 (1 H, m), 7 29-7.41 (2H, m), 7.55-7.66 (1H, m), 8.33 (1H, s), 9.93 (1H, br).

Example 66
(R) -4-bromophenylcarbamic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester yield 62%
¹ H-NMR (DMSO-d ₆ ) δ ppm:
1.15 (3 H, s), 3.99 (2 H, s), 4. 13 (2 H, s), 5. 40 (1 H, s), 7.34-7.53 (4 H, m), 8 .33 (1 H, s), 9.86 (1 H, br).

Example 67
(R) -4-trifluoromethylphenylcarbamic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester yield 83%
¹ H-NMR (DMSO-d ₆ ) δ ppm:
1.16 (3 H, s), 4.02 (2 H, s), 4. 14 (2 H, s), 5.42 (1 H, s), 7.58-7. 74 (4 H, m), 8 .34 (1 H, s), 10. 14 (1 H, br).

Example 68
(R) -4-Trifluoromethoxyphenylcarbamic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester yield 58%
¹ H-NMR (DMSO-d ₆ ) δ ppm:
1.15 (3 H, s), 3.99 (2 H, s), 4. 13 (2 H, s), 5.4 1 (1 H, s), 7.31 (2 H, d, J = 8.5 Hz) , 7.58 (2 H, d, J = 8.5 Hz), 8.33 (1 H, s), 9. 92 (1 H, br).

Example 69
(R) -4-Fluorophenylcarbamic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester yield 95%
¹ H-NMR (DMSO-d ₆ ) δ ppm:
1.15 (3 H, s), 3.98 (2 H, s), 4.12 (2 H, s), 5. 39 (1 H, s), 7. 10-7. 17 (2 H, m), 7 45-7.51 (2H, m), 8.33 (1 H, s), 9.73 (1 H, br).

Example 70
(R) -benzylcarbamic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester yield 72%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.20 (3H, s), 3.61 (1H, br), 3.97-4.04 (3H, m), 4.23 (1H, d, J = 12.0 Hz), 4.70- 4.89 (1 H, m), 7.13-7.39 (5 H, m), 8.01 (1 H, s).

Example 71
(R) -Methylcarbamic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester yield 73%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.21 (3 H, s), 2.80 (3 H, d, J = 4.8 Hz), 3.57 (1 H, br), 3.98-4.16 (3 H, m), 4.24 ( 1 H, d, J = 12.3 Hz), 4.72 to 4.91 (1 H, m), 8.03 (1 H, s).

Example 72
Preparation of (R) -N-methyl-N- (4-trifluoromethoxybenzyl) carbamic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester N- (R) -2-Chloro-1-l prepared in Example 10 in a suspension of methyl-N- (4-trifluoromethoxybenzyl) carbamyl chloride (2.05 g, 7.65 mmol) in toluene (40 ml) (2,3-Dihydroxy-2-methylpropyl) -4-nitroimidazole (2.16 g, 9.18 mmol), N-ethyldiisopropylamine (2.67 ml, 15.30 mmol) and 4-dimethylaminopyridine ( 0.19 g (1.53 mmol) was added and stirred at 100 ° C. for 3.5 hours. The reaction mixture was diluted with ethyl acetate, washed with 10% hydrochloric acid, dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 9/1) to give (R) -N-methyl-N- (4-trifluoromethoxybenzyl) carbamic acid 3- (2-) as a colorless oil. Chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester (2.74 g, 77% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.25 (3H, s), 2.83 (3H, s), 3.87-4.17 (4H, m), 4.44 (2H, s), 7.18-7. 25 (4H, s) m), 8.05 (1 H, s).

Example 73
Preparation of (R) -N-methyl-N- (4-trifluoromethoxybenzyl) carbamic acid 2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl ester (R) -N-Methyl-N- (4-trifluoromethoxybenzyl) carbamic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methyl prepared in Example 72 To a solution of propyl ester (2.74 g, 5.87 mmol) in DMF (20 ml) was added sodium hydride (0.28 g, 7.04 mmol) with stirring under ice cooling, and the mixture was further stirred at 0 ° C. for 1 hour. Ice water was added to the reaction solution, and the precipitate was collected by filtration and washed with water. Recrystallization from isopropanol and white solid of (R) -N-methyl-N- (4-trifluoromethoxybenzyl) carbamic acid 2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] Oxazol-2-ylmethyl ester (1.40 g, 55% yield) was obtained.
Mp 123-124 ° C.

Example 74
Preparation of (R) -N- (4-chlorophenyl) -N-cyclohexylcarbamic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester N- (4-) (R) -2-Chloro-1- (2,3-dihydroxy-) prepared in Example 10 in a suspension of chlorophenyl) -N-cyclohexylcarbamoyl chloride (1.56 g, 6.05 mmol) in toluene (10 ml) 2-Methylpropyl) -4-nitroimidazole (0.95 g, 4.03 mmol), N-ethyldiisopropylamine (1.45 ml, 8.06 mmol) and 4-dimethylaminopyridine (0.10 g, 0.81) Add millimoles) and stir at 100 ° C. for 3 hours. The reaction mixture was diluted with ethyl acetate, washed with 10% hydrochloric acid, dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 9/1) to give white amorphous (R) -N- (4-chlorophenyl) -N-cyclohexylcarbamic acid 3- (2-chloro-4- 4 Nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester (0.75 g, 40% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
0.78-1.22 (6H, m), 1.24-1.48 (2H, m), 1.54-1.67 (1H, m), 1.70-1.93 (4H, m) ), 2.87-3.13 (1 H, m), 3.72-3.98 (3 H, m), 4.00-4.24 (2 H, m), 7.00-7.06 (2 H) , M), 7.35-7.41 (2H, m), 7.80 (1 H, br).

Example 75
Preparation of (R) -N- (4-Chlorophenyl) -N-cyclohexylcarbamic acid 2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl ester Example 74 Prepared (R) -N- (4-chlorophenyl) -N-cyclohexylcarbamic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester (0.75 g) Sodium hydride (76 mg, 1.91 mmol) was added to a solution of 1.59 mmol) in DMF (7 ml) with ice cooling, and the mixture was further stirred at 0 ° C. for 0.5 hour. Ice water is added to the reaction mixture, and the mixture is extracted with ethyl acetate, washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue is recrystallized with isopropanol and (R) -N- (4-chlorophenyl) -N-cyclohexylcarbamic acid 2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole as a white solid 2-yl methyl ester (0.53 g, 77% yield) was obtained.
Melting point 175-177 [deg.] C.

Example 76
Preparation of (R) -N-methyl-N- (4-trifluoromethoxyphenyl) carbamic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester Example To a suspension of (R) -2-chloro-1- (2,3-dihydroxy-2-methyl) propyl-4-nitroimidazole (0.82 g, 3.48 mmol) prepared in 10 in toluene (10 ml) N-Methyl-N- (4-trifluoromethoxyphenyl) carbamoyl chloride (1.33 g, 5.23 mmol), N-ethyldiisopropylamine (1.2 ml, 6.97 mmol) and 4-dimethylaminopyridine (85 mg) , 0.70 mmol) was added and stirred at 100 ° C. for 5 hours. The reaction solution was diluted with ethyl acetate, washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (n-hexane / ethyl acetate = 2/1) to obtain slightly yellow amorphous (R) -N-methyl-N- (4-trifluoromethoxyphenyl) carbamic acid 3- (2) -Chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester (1.04 g, yield 65%) was obtained.
¹ H-NMR (DMSO-d ₆ ) δ ppm:
1.02 (3H, s), 3.26 (3H, s), 3.80-4.00 (4H, m), 5.39 (1H, s), 7.37-7.40 (2H, 2) m), 7.47-7.52 (2 H, m), 8. 25 (1 H, s).

Example 77
Preparation of (R) -N-methyl-N- (4-trifluoromethoxyphenyl) carbamic acid 2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl ester (R) -N-Methyl-N- (4-trifluoromethoxyphenyl) carbamic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methyl prepared according to Example 76 Sodium hydride (0.48 g, 11.9 mmol) was added to a solution of propyl ester (4.50 g, 9.94 mmol) in DMF (13.5 ml) with ice cooling, and the mixture was stirred at room temperature for 1 hour. Water and ethyl acetate were added to the reaction mixture, and the precipitate was collected by filtration. The crude crystals are recrystallized from isopropanol and (R) -N-methyl-N- (4-trifluoromethoxyphenyl) carbamic acid 2-methyl-6-nitro-2,3-dihydroimidazo [2 1-b] oxazol-2-ylmethyl ester (2.95 g, 71% yield) was obtained.
Melting point 144-145 ° C
Optical purity 99.8% ee
[Α] _D ²⁴ = 7.68 ° (concentration: 0.938, CHCl ₃ ).

  The compounds of Example 78 and Example 79 were produced in the same manner as in Example 77, using the corresponding starting materials.

Example 78
(R) -Methylcarbamic acid 2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl ester yield 26%, mp 175-178 ° C.

Example 79
(R) -Diethylcarbamic acid 2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl ester yield 27%, mp 196-197 ° C.

Example 80
Preparation of (R) -N- (4-Chlorophenyl) -N-methylcarbamic acid 2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl ester Example 64 DMSO of (R) -4-chlorophenylcarbamic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester (1.5 g, 3.8 mmol) prepared To the solution was added iodomethane (0.71 ml, 11.4 mmol) and potassium hydroxide (0. 64 g, 11.4 mmol) and stirred at room temperature for 4 hours. After ice-cooling, 10% hydrochloric acid was added, and the mixture was extracted with ethyl acetate, washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (n-hexane / ethyl acetate = 1/1), recrystallized with isopropanol, and (R) -N- (4-chlorophenyl) -N-methylcarbamic acid 2-methyl of white solid -6-Nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl ester (0.67 g, 60% yield) was obtained.
Melting point 131-133 ° C
Optical purity 99.8% ee
[Α] _D ²⁶ = 22.86 ° (concentration: 1.028, CHCl ₃ ).

Example 81
Preparation of (R) -Bis (4-chlorophenyl) carbamic acid 2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl ester Prepared as in Example 37 (R ) 2-Hydroxymethyl-2-methyl-6-nitro-2, 3-dihydroimidazo [2,1-b] oxazole (0.30 g, 1.5 mmol) in ice in a suspension of methylene chloride (15 ml) Under cold stirring, pyridine (0.37 ml, 4.5 mmol) and triphosgene (0.16 g, 0.5 mmol) were added, and the mixture was further stirred at room temperature for 2.5 hours. To the reaction mixture was added bis (4-chlorophenyl) amine (0.39 g, 1.6 mmol), and the mixture was further stirred at room temperature for 20 hours. The reaction solution is ice-cooled, 10% hydrochloric acid is added, extraction is carried out with methylene chloride, after drying with magnesium sulfate, concentration under reduced pressure and the residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 19/1). Recrystallization from isopropanol and white solid of (R) -bis (4-chlorophenyl) carbamic acid 2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl ester ( 82 mg, yield 12%) were obtained.
Mp 200-201 ° C.

Example 82
Preparation of piperidine-1-carboxylic acid 2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl ester 2-hydroxymethyl-2-methyl prepared in Example 33 Pyridine (0.37 ml) in a suspension of -6-nitro-2,3-dihydroimidazo [2,1-b] oxazole (0.3 g, 1.5 mmol) in methylene chloride (15 ml) with ice cooling. 4.5 mmol) and triphosgene (0.18 g, 0.6 mmol) were added and further stirred at room temperature for 2 hours. The reaction solution was ice-cooled, piperidine (0.16 ml, 1.7 mmol) was added, and the mixture was further stirred at room temperature for 3 hours. The reaction solution was ice-cooled, 10% hydrochloric acid was added, the insoluble matter was removed by filtration and washed with methylene chloride. The filtrate was separated, and the organic phase was dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (n-hexane / ethyl acetate = 3/2), recrystallized with methylene chloride and diisopropyl ether, and white solid piperidine-1-carboxylic acid 2-methyl-6-nitro-2 is obtained. 3, 3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl ester (65 mg, 14% yield) was obtained.
Melting point 152-154 [deg.] C.

Example 83
Preparation of 4- (4-Trifluoromethoxyphenyl) piperazine-1-carboxylic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester Prepared as in Example 3 4- (4-trifluoromethoxy) in a suspension of 2-chloro-1- (2,3-dihydroxy-2-methylpropyl) -4-nitroimidazole (0.30 g, 1.3 mmol) in toluene (5 ml) Add phenyl) piperazine-1-carbonyl chloride (0.26 g, 0.85 mmol), N-ethyldiisopropylamine (0.30 ml, 1.7 mmol) and 4-dimethylaminopyridine (21 mg, 0.17 mmol) The mixture was stirred at 100 ° C. for 2.5 hours. It was diluted with ethyl acetate, washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 9/1) to give 4- (4-trifluoromethoxyphenyl) piperazine-1-carboxylic acid 3- (2-chloro-4) as a slightly yellow oil. -Nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester (0.24 g, 55% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.26 (3H, s), 3.02-3.17 (4H, m), 3.39-3.72 (4H, m), 3.91 (1H, s), 3.99-4. 18 (3 H, m), 4. 34 (1 H, d, J = 12.3 Hz), 6.85-6.98 (2 H, m), 7.09-7.22 (2 H, m), 8. 05 (1 H, s).

Example 84
Preparation of 4- (4-Trifluoromethoxyphenyl) piperazine-1-carboxylic acid 2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl ester Example 83 4- (4-Trifluoromethytoxyphenyl) piperazine-1-carboxylic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester prepared (0.24 g, Sodium hydride (23 mg, 0.56 mmol) was added to a solution of 0.47 mmol) in DMF (2 ml) under ice cooling, and the mixture was further stirred at 0 ° C. for 1 hour. Ice water is added to the reaction mixture, and the mixture is extracted with ethyl acetate, washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (ethyl acetate), washed with diisopropyl ether and 4- (4-trifluoromethoxyphenyl) piperazine-1-carboxylic acid 2-methyl 6-nitro-2,3-white solid. Dihydroimidazo [2,1-b] oxazol-2-ylmethyl ester (0.13 g, 58% yield) was obtained.
Melting point 138-140 [deg.] C.

Example 85
4- (4-Trifluoromethylphenyl) -1,2,3,6-tetrahydropyridine-1-carboxylic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methyl Preparation of propyl ester A suspension of 4- (4-trifluoromethylphenyl) -1,2,3,6-tetrahydropyridine-1-carbonyl chloride (0.10 g, 0.38 mmol) in toluene (3 ml), 2-chloro-1- (2,3-dihydroxy-2-methylpropyl) -4-nitroimidazole (0.13 g, 0.57 mmol) prepared in Example 3, N-ethyldiisopropylamine (0.13 ml, 0.76 mmol), 4-dimethylaminopyridine (10 mg, 0.08 mmol) were added and stirred at 100 ° C. for 2.5 hours. The reaction solution was diluted with ethyl acetate, washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 9/1) to give 4- (4-trifluoromethylphenyl) -1,2,3,6-tetrahydropyridine-1-carvone as colorless oil. The acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester (0.11 g, 59% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.26 (3 H, s), 2.43-2.50 (2 H, m), 3.50-3.78 (2 H, m), 3.93-4.24 (5 H, m), 7. 46 (1 H, d, J = 8.3 Hz), 7. 60 (1 H, d, J = 8.3 Hz), 8.05 (1 H, s).

Example 86
4- (4-trifluoromethylphenyl) -1,2,3,6-tetrahydropyridine-1-carboxylic acid 2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole-2 Preparation of 4-ylmethyl ester 4- (4-Trifluoromethylphenyl) -1,2,3,6-tetrahydropyridine-1-carboxylic acid 3- (2-chloro-4-nitroimidazole) prepared in Example 85 To a solution of 1-yl) -2-hydroxy-2-methylpropyl ester (0.11 g, 0.23 mmol) in DMF (1 ml) was added sodium hydride (11 mg, 0.28 mmol) under ice-cooling and stirring. The mixture was further stirred at 0 ° C. for 1 hour. Ice water is added to the reaction mixture, and the mixture is extracted with ethyl acetate, washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 4/1), washed with diisopropyl ether, and 4- (4-trifluoromethylphenyl) -1,2,3,6-tetrahydroline as a white solid. Pyridine-1-carboxylic acid 2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl ester (0.04 g, 39% yield) was obtained.
113-115 ° C.

Example 87
Preparation of (R) -4-tert-butoxycarbonylpiperazine-1-carboxylic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester 4-chlorocarbonylpiperazine- (R) -2-Chloro-1- (2,3-dihydroxy-) prepared in Example 10 in a suspension of 1-carboxylic acid tert-butyl ester (3.34 g, 13.42 mmol) in toluene (70 ml) 2-Methylpropyl) -4-nitroimidazole (4.43 g, 18.79 mmol), N-ethyldiisopropylamine (4.68 ml, 26.84 mmol) and 4-dimethylaminopyridine (0.33 g, 2.68) Add millimoles) and stir at 100 ° C. for 4.5 hours. The reaction solution was diluted with ethyl acetate, washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (n-hexane / methylene chloride / ethyl acetate = 45/45/10) to give (R) -4-tert-butoxycarbonylpiperazine-1-carboxylic acid 3- (colorless oil) 2-Chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester was obtained (4.12 g, yield 69%).
¹ H-NMR (CDCl ₃ ) δ ppm:
1.23 (3H, s), 1.47 (9 H, s), 3.33-3.50 (8 H, m), 3.91 (1 H, s), 3.99-4.16 (3 H, 3 H, s) m), 4.30 (1 H, d, J = 12.1 Hz), 8.04 (1 H, s).

  Example using 4- (4-trifluoromethoxybenzyloxycarbonyl) piperazine-1-carbonyl chloride or 4- [3- (4-trifluoromethylphenyl) -2-propenyloxycarbonyl] piperazine-1-carbonyl chloride Analogously to Example 87, the compounds of Example 88 and Example 89 were produced.

Example 88
(R) -2-Chloro-1- {3- [4- (4-trifluoromethoxybenzyloxycarbonyl) piperazin-1-ylcarbonyloxy] -2-hydroxy-2-methylpropyl} -4-nitroimidazole 81% rate
¹ H-NMR (CDCl ₃ ) δ ppm:
1.24 (3H, s), 3.28-3.61 (8H, m), 3.89 (1H, s), 4.00-4.20 (3H, m), 4.31 (1H, 1) d, J = 12.5 Hz), 5.14 (2 H, s), 7.22 (2 H, d, J = 8.7 Hz), 7.39 (2 H, d, J = 8.7 Hz), 8. 04 (1 H, s).

Example 89
(R) -2-chloro-1- {3- [4- [3- (4-trifluoromethylphenyl) -2-propenylcarbonyl] piperazin-1-ylcarbonyloxy] -2-hydroxy-2-methylpropyl } -4-Nitroimidazole yield 95%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.24 (3 H, s), 3.33-3.61 (8 H, m), 3. 90 (1 H, s), 3.99-4. 17 (3 H, m), 4.31 (1 H, 1 H, s) d, J = 12.1 Hz), 4.79 (2 H, d, J = 6.1 Hz), 6.39 (1 H, dt, J = 6.1 Hz, 15.9 Hz), 6.67 (1 H, d , J = 15.9 Hz), 7.39 (2 H, d, J = 8.3 Hz), 7.49 (2 H, d, J = 8.3 Hz), 8.04 (1 H, s).

Example 90
Preparation of (R) -4- (4-Chlorobenzyl) piperazine-1-carboxylic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester 4- (4) (Chloro) benzyl) piperazine-1-carbonyl chloride (2.20 g, 8.05 mmol) in toluene (30 ml), the (R) -2-chloro-1- (2,3) prepared in Example 10 -Dihydroxy-2-methyl) propyl-4-nitroimidazole (2.28 g, 9.66 mmol), N-ethyldiisopropylamine (2.81 ml, 16.10 mmol) and 4-dimethylaminopyridine (0.20 g, 1.61 mmol) was added and stirred at 100 ° C. for 3 hours. The reaction solution was diluted with ethyl acetate, washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 9/1) to give (R) -4- (4-chlorobenzyl) piperazine-1-carboxylic acid 3- (2-chloro-) as a yellow oil. 4-Nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester (1.82 g, yield 48%) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.23 (3 H, s), 2.17-2. 50 (4 H, m), 2.55 (1 H, s), 3.26- 3.52 (6 H, m), 3.98-4. 20 (3H, m), 4.30 (1 H, d, J = 12.4 Hz), 7.23-7.32 (4 H, m), 8.05 (1 H, s).

  The compounds of Example 91 and Example 92 were produced in the same manner as in Example 90, using the corresponding starting materials.

Example 91
(R) -2-Chloro-1- {3- [4- (4-trifluoromethylbenzyl) piperazin-1-ylcarbonyloxy] -2-hydroxy-2-methylpropyl} -4-nitroimidazole yield 31 %
¹ H-NMR (CDCl ₃ ) δ ppm:
1.23 (3H, s), 2.24-2.54 (4H, m), 3.24-3.50 (4H, m), 3.56 (2H, s), 3.97-4. 20 (3 H, m), 4.32 (1 H, d, J = 12.4 Hz), 7. 45 (2 H, d, J = 8.0 Hz), 7.58 (2 H, d, J = 8.0 Hz ), 8.05 (1 H, s).

Example 92
(R) -2-Chloro-1- {3- [4- (4-trifluoromethoxybenzyl) piperazin-1-ylcarbonyloxy] -2-hydroxy-2-methylpropyl} -4-nitroimidazole yield 47 %
¹ H-NMR (CDCl ₃ ) δ ppm:
1.23 (3 H, s), 2.22-2.54 (4 H, m), 3.30-3.54 (4 H, m), 3.50 (2 H, s), 3.97-4. 16 (3H, m), 4.32 (1H, d, J = 12.5 Hz), 7.15 to 7.18 (2H, m), 7.32 to 7.36 (2H, m), 8. 05 (1 H, s).

Example 93
Preparation of (R) -4- (4-Trifluoromethoxyphenyl) piperazine-1-carboxylic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester Example To a suspension of (R) -2-chloro-1- (2,3-dihydroxy-2-methylpropyl) -4-nitroimidazole (0.65 g, 2.8 mmol) prepared in 10 in toluene (13 ml) 4- (4-Trifluoromethoxyphenyl) piperazine-1-carbonyl chloride (1.25 g, 4.2 mmol), N-ethyldiisopropylamine (0.96 ml, 5.6 mmol) and 4-dimethylaminopyridine (67 mg) 0.56 mmol) was added and stirred at 100 ° C. for 8.5 hours. The reaction solution was diluted with ethyl acetate, washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 19/1) to give (R) -4- (4-trifluoromethoxyphenyl) piperazine-1-carboxylic acid 3- (2-) as a yellow oil. Chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester (1.29 g, 92% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.26 (3H, s), 3.02-3.17 (4H, m), 3.39-3.72 (4H, m), 3.91 (1H, s), 3.99-4. 18 (3 H, m), 4. 34 (1 H, d, J = 12.3 Hz), 6.85-6.98 (2 H, m), 7.09-7.22 (2 H, m), 8. 05 (1 H, s).

  The compounds of Example 94 to Example 102 were produced in the same manner as in Example 93, using the corresponding starting materials.

Example 94
(R) -4- (4-trifluoromethylphenyl) piperazine-1-carboxylic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester yield 48%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.26 (3H, s), 3.13-3.35 (4H, m), 3.48-3.72 (4H, m), 3.94 (1H, s), 4.00-4. 18 (3H, m), 4.33 (1 H, d, J = 12.3 Hz), 6.93 (2 H, d, J = 8.6 Hz), 7.50 (2 H, d, J = 8.6 Hz ), 8.05 (1 H, s).

Example 95
(R) -4- (4-methoxyphenyl) piperazine-1-carboxylic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester yield 54%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.24 (3 H, s), 2.93-3.09 (4 H, m), 3.52-3.63 (4 H, m), 3.77 (3 H, s), 3.96 (1 H, 1 H, s) s), 4.00-4. 19 (3 H, m), 4.32 (1 H, d, J = 12.3 Hz), 6.82-6.92 (4 H, m), 8.05 (1 H, 1 H, m) s).

Example 96
(R) -4- (4-chlorophenyl) piperazine-1-carboxylic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester yield 81%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.25 (3 H, s), 3.00-3. 13 (4 H, m), 3.52-3. 65 (4 H, m), 3.93 (1 H, s), 4.00-4. 17 (3H, m), 4.33 (1H, d, J = 12.5 Hz), 6.82-6.86 (2H, m), 7.20-7.25 (2H, m), 8. 05 (1 H, s).

Example 97
(R) -4- (3-chlorophenyl) piperazine-1-carboxylic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester yield 87%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.25 (3 H, s), 3.04-3.22 (4 H, m), 3.43-3.70 (4 H, m), 3.89 (1 H, s), 4.00-4. 17 (3 H, m), 4.33 (1 H, d, J = 12.3 Hz), 6.78 (1 H, ddd, J = 1.6 Hz, 2.4 Hz, 8.4 Hz), 6.85-6 .88 (2 H, m), 7.19 (1 H, t, J = 8.4 Hz), 8.05 (1 H, s).

Example 98
(R) -4- (3,4-Dichlorophenyl) piperazine-1-carboxylic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester yield 47%
¹ H-NMR (DMSO-d ₆ ) δ ppm:
1.12 (3H, s), 3.15-3.26 (4H, m), 3.39-3.61 (4H, m), 3.88 (1 H, d, J = 11.0 Hz), 3.93 (1 H, d, J = 11.0 Hz), 4.07 (1 H, d, J = 14.7 Hz), 4.15 (1 H, d, J = 14.7 Hz), 6.96 (1 H , Dd, J = 2.9 Hz, 9.1 Hz), 7.16 (1 H, d, J = 2.9 Hz), 7.42 (1 H, d, J = 9.1 Hz), 8.34 (1 H) , S).

Example 99
(R) -4- (4-Fluorophenyl) piperazine-1-carboxylic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester 100% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
1.25 (3 H, s), 2.96-3.09 (4 H, m), 3.50-3.67 (4 H, m), 3.98 (1 H, s), 4.05-4. 16 (3 H, m), 4.33 (1 H, d, J = 12.3 Hz), 6.85-7.02 (4 H, m), 8.05 (1 H, s).

Example 100
(R) -4- (3-trifluoromethylphenyl) piperazine-1-carboxylic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester yield 83%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.25 (3 H, s), 3.11-3.26 (4 H, m), 3.48-3. 70 (4 H, m), 3.91 (1 H, s), 4.00-4. 24 (3 H, m), 4.33 (1 H, d, J = 12.3 Hz), 7.02-7.20 (3 H, m), 7.38 (1 H, t, J = 8.0 Hz), 8.05 (1 H, s).

Example 101
(R) -2-chloro-1- (3-diethylaminocarbonyloxy-2-hydroxy-2-methylpropyl) -4-nitroimidazole yield 37%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.11 (6 H, t, J = 7.1 Hz), 1.20 (3 H, s), 3.16 (4 H, q, J = 7.1 Hz), 3.76 (1 H, br), 4. 06-4.11 (3 H, m), 4.26 (1 H, d, J = 11.1 Hz), 8.05 (1 H, s).

Example 102
2-Chloro-1- (3-morpholinocarbonyloxy-2-hydroxy-2-methylpropyl) -4-nitroimidazole 100% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
1.23 (3H, s), 3.35-3. 52 (4H, m), 3.61-3. 72 (4H, m), 3.99-4. 16 (3H, m), 4.. 31 (1 H, d, J = 12.3 Hz), 8.05 (1 H, s).

Example 103
(R) -4- (4-Trifluoromethylbenzylideneamino) piperazine-1-carboxylic acid Preparation of 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester 4 (R) -2-chloro-1 prepared in Example 10 in a suspension of 4- (4-trifluoromethylbenzylideneamino) piperazine-1-carbonyl chloride (2.48 g, 7.77 mmol) in toluene (40 ml) -(2,3-Dihydroxy-2-methylpropyl) -4-nitroimidazole (2.75 g, 11.66 mmol), N-ethyldiisopropylamine (2.71 ml, 15.54 mmol) and 4-dimethylaminopyridine (0.19 g, 1.55 mmol) was added and stirred at 100 ° C. for 2.5 hours. The reaction mixture was diluted with ethyl acetate, washed with 10% hydrochloric acid, dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 9/1) to give (R) -4- (4-trifluoromethylbenzylideneamino) piperazine-1-carboxylic acid 3- (2) as a yellow oil. -Chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester (4.03 g, quantitative) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.25 (3 H, s), 3.04-3.33 (4 H, m), 3.48-3.76 (4 H, m), 3.83 (1 H, s), 4.00-4. 17 (3 H, m), 4.33 (1 H, d, J = 12.3 Hz), 7.55 (1 H, s), 7.59 (2 H, d, J = 8.4 Hz), 7.69 ( 2H, d, J = 8.4 Hz), 8.04 (1 H, s).

Example 104
Preparation of (R) -4- (4-trifluoromethylphenoxy) piperidine-1-carboxylic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester 4- (R) -2-chloro-1-l prepared in Example 10 in a suspension of (4-trifluoromethylphenoxy) piperidine-1-carbonyl chloride (0.72 g, 2.34 mmol) in toluene (40 ml) Add (2,3-dihydroxy-2-methylpropyl) -4-nitroimidazole (1.16 g, 4.68 mmol) and triethylamine (1.63 ml, 11.70 mmol) and stir at 100 ° C. for 2.5 hours did. The reaction solution was diluted with ethyl acetate, washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 9/1) to give (R) -4- (4-trifluoromethylphenoxy) piperidine-1-carboxylic acid 3- (2-) as a colorless oil. Chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester (184 mg, 16% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.24 (3H, s), 1.72-1.98 (4H, m), 3.33-3.67 (4H, m), 3.91-4.20 (3H, m), 4.. 24-4. 39 (1 H, m), 4.52-4. 65 (1 H, m), 6.96 (2 H, d, J = 8.7 Hz), 7.55 (2 H, d, J = 8 .7 Hz), 8.05 (1 H, s).

Example 105
Preparation of (R) -4- (4-trifluoromethylphenylamino) piperidine-1-carboxylic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester 4 (R) -2-Chloro-1 prepared in Example 10 in a suspension of 4- (4-trifluoromethylphenylamino) piperidine-1-carbonyl chloride (1.43 g, 4.67 mmol) in toluene (30 ml) -(2,3-Dihydroxy-2-methylpropyl) -4-nitroimidazole (1.54 g, 7.01 mmol), N-ethyldiisopropylamine (1.63 ml, 9.34 mmol), 4-dimethylaminopyridine (0.11 g, 0.93 mmol) was added and stirred at 100 ° C. for 2.5 hours. The reaction solution was diluted with ethyl acetate, washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 9/1) to give (R) -4- (4-trifluoromethylphenylamino) piperidine-1-carboxylic acid 3- (yellowish oil) 2-Chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester was obtained (1.44 g, yield 61%).
¹ H-NMR (CDCl ₃ ) δ ppm:
1.25 (3 H, s), 1.30-1. 48 (2 H, m), 1.98-2.13 (2 H, m), 2.83-3. 13 (2 H, m), 3. 37-3.61 (1 H, m), 3.83-3.96 (2 H, m), 3.96-4.22 (4 H, m), 4.34 (1 H, d, J = 11.8 Hz 7.40 (2H, d, J = 8.5 Hz), 7.60 (2H, d, J = 8.5 Hz), 8.07 (1 H, s).

Example 106
(R) -4- (4-Trifluoromethylphenyl) -1,2,3,6-tetrahydropyridine-1-carboxylic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy Preparation of 2-methylpropyl ester 4- (4-Trifluoromethylphenyl) -1,2,3,6-tetrahydropyridine-1-carbonyl chloride (0.60 g, 2.07 mmol) in toluene (36 ml) To the suspension, (R) -2-chloro-1- (2,3-dihydroxy-2-methyl) propyl-4-nitroimidazole (0.74 g, 3.11 mmol) prepared in Example 10 and triethylamine 1.74 ml, 12.42 mmol) were added and stirred at 100 ° C. for 16 hours. It was diluted with ethyl acetate, washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 9/1) to give (R) -4- (4-trifluoromethylphenyl) -1,2,3,6-tetrahydro oil as a slightly yellow oil. Pyridine-1-carboxylic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester (0.32 g, 31% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.26 (3 H, s), 2.43-2.50 (2 H, m), 3.50-3.78 (2 H, m), 3.93-4.24 (5 H, m), 7. 46 (2H, d, J = 8.3 Hz), 7.60 (2 H, d, J = 8.3 Hz), 8.05 (1 H, s).

  The compounds of Examples 107 to 112 were produced in the same manner as in Example 106, using the corresponding starting materials.

Example 107
(R) -4- (4-Chlorophenyl) -1,2,3,6-tetrahydropyridine-1-carboxylic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-hydroxy-2- (2-chloro) Production yield of methyl propyl ester 94%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.25 (3 H, s), 2.41-2. 59 (2 H, m), 3.50 to 3. 78 (2 H, m), 3.93 to 4.22 (6 H, m), 4. 35 (1 H, d, J = 12.3 Hz), 5.87-6.13 (1 H, m), 7.26-7. 37 (4 H, m), 8.05 (1 H, s).

Example 108
(R) -4- (4-Trifluoromethoxyphenyl) -1,2,3,6-tetrahydropyridine-1-carboxylic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxyl -2- methyl propyl ester yield 92%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.26 (3 H, s), 2.46-2.59 (2 H, m), 3. 13-3. 37 (1 H, m), 3.50-3.74 (2 H, m), 4. 00-4.14 (6 H, m), 4.36 (1 H, d, J = 12.4 Hz), 7.19 (2 H, d, J = 8.0 Hz), 7.37 (2 H, d, J = 8.0 Hz), 8.05 (1 H, s).

Example 109
(R) -4- (4-Methoxyphenyl) -1,2,3,6-tetrahydropyridine-1-carboxylic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2 -Methyl propyl ester yield 63%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.23 (3 H, s), 2.43-2.61 (2 H, m), 3.52-3.74 (2 H, m), 3.82 (3 H, s), 4.01-4. 16 (5 H, m), 4. 34 (1 H, d, J = 12.6 Hz), 5. 38-6.00 (1 H, m), 6. 88 (2 H, d, J = 8.8 Hz), 7.30 (2H, d, J = 8.8 Hz), 8.05 (1 H, s).

Example 110
(R) -4- (3-Trifluoromethylphenyl) -1,2,3,6-tetrahydropyridine-1-carboxylic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy -2- methyl propyl ester yield 54%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.25 (3 H, s), 2.46 to 2. 70 (2 H, m), 3.50 to 3.78 (2 H, m), 4.00 to 4. 32 (6 H, m), 4. 35 (1 H, d, J = 12.6 Hz), 5.98-6.22 (1 H, m), 7. 39-7. 67 (4 H, m), 8.06 (1 H, s).

Example 111
(R) -4- (4-bromophenyl) -1,2,3,6-tetrahydropyridine-1-carboxylic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2 -Methyl propyl ester yield 80%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.25 (3 H, s), 2.41-2. 63 (2 H, m), 3.50-3.76 (2 H, m), 3.96-4. 20 (6 H, m), 4.. 35 (1H, d, J = 12.3 Hz), 5.87-6.13 (1H, m), 7.15-7.26 (2H, m), 7.43-7.48 (2H, m) ), 8.05 (1 H, s).

Example 112
(R) -4- (4-Fluorophenyl) -1,2,3,6-tetrahydropyridine-1-carboxylic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2 -Methyl propyl ester yield 57%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.25 (3 H, s), 2.41-2. 63 (2 H, m), 3.50-3.76 (2 H, m), 3.89-4.22 (6 H, m), 4. 35 (1H, d, J = 12.6 Hz), 5.83-6.04 (1H, m), 6.99-7.06 (2H, m), 7.29-7. 35 (2H, m) ), 8.05 (1 H, s).

  5-chloro-2,3-dihydroindole-1-carbonyl chloride, 5-chloro-1,3-dihydroisoindole-2-carbonyl chloride, 6-chloro-3,4-dihydro-1H-isoquinoline-2-carbonyl The compounds of Example 113 to Example 116 were prepared in the same manner as in Example 106 using chloride or 6-chloro-3,4-dihydro-2H-quinoline-1-carbonyl chloride.

Example 113
(R) -5-Chloroindolinyl-1-carboxylic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester slightly yellow amorphous, 50% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
1.27 (3 H, s), 3. 14 (2 H, t, J = 8.5 Hz), 3.42 (1 H, br), 3.91-4.28 (5 H, m), 4.37 ( 1 H, d, J = 11.8 Hz), 7.04 to 7.24 (2 H, m), 7.73 (1 H, d, J = 8.3 Hz), 8.04 (1 H, s).

Example 114
(R) -5-Chloroisoindolinyl-2-carboxylic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester brown solid, 19% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
1.27 (3 H, s), 3.93 (1 H, d, J = 7.8 Hz), 4.04-4.24 (7 H, m), 4.32 (1 H, d, J = 11.8 Hz) ], 7.16-7.29 (3 H, m), 8.07 (1 H, s).

Example 115
(R) -6-Chloro-3,4-dihydro-1H-isoquinoline-2-carboxylic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester slightly yellow Oil, 63% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
1.24 (3H, s), 2.83 (2H, t, J = 5.8 Hz), 3.46-3.76 (2H, m), 3.90 (1 H, d, J = 5.3 Hz) ), 4.01 to 4.15 (3 H, m), 4. 34 (1 H, d, J = 12.3 Hz), 4.43 to 4.65 (2 H, m), 6.93 to 7.09. (1 H, m), 7.09-7. 22 (2 H, m), 8.04 (1 H, s).

Example 116
(R) -6-Chloro-3,4-dihydro-2H-quinoline-1-carboxylic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester slightly yellow Oil, 70% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
1.26 (3H, s), 1.87-2.00 (2H, m), 2.76 (2H, t, J = 6.5 Hz), 3.27 (1 H, br), 3.57- 3.83 (2H, m), 3.98-4.17 (3H, m), 4.33 (1H, d, J = 12.0 Hz), 7.12-7.16 (2H, m), 7.41-7.61 (1 H, br), 7.98 (1 H, s).

Example 117
Preparation of (R) -4-tert-butoxycarbonylpiperazine-1-carboxylic acid 2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl ester (R) -4-tert-Butoxycarbonylpiperazine-1-carboxylic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester (4.12 g, 9) Sodium hydride (0.44 g, 11.04 mmol) was added to a solution of 20 mmol) in DMF (30 ml) with ice cooling, and the mixture was stirred at 0 ° C. for 1 hour. Ice water is added to the reaction solution, the precipitate is collected by filtration, the crude crystals are purified by silica gel column chromatography (ethyl acetate), washed with isopropanol, and (R) -4-tert-butoxycarbonylpiperazine-1 as a white solid. Carboxylic acid 2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl ester (2.24 g, 59% yield) was obtained.
Mp 211-212 ° C.

Example 118
Preparation of (R) -4- (4-Trifluoromethoxyphenyl) piperazine-1-carboxylic acid 2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl ester (R) -4- (4-Trifluoromethytoxyphenyl) piperazine-1-carboxylic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-hydroxy-2- (2-hydroxy) -2- (2-hydroxy) -4-hydroxy-4- (2-methoxy-2-hydroxyimidazole) To a solution of methyl propyl ester (1.29 g, 2.5 mmol) in DMF (13 ml) was added sodium hydride (0.12 g, 3 mmol) under ice cooling with stirring and further stirred at 0 ° C. for 1 hour. Ice water is added to the reaction solution, and the precipitate is collected by filtration, washed with water, recrystallized from isopropanol, and (R) -4- (4-trifluoromethoxyphenyl) piperazine-1-carboxylic acid 2- (white solid). Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl ester (0.70 g, 59% yield) was obtained.
Optical purity 99.6% ee
[Α] _D ²⁵ = 0.99 ° (concentration: 0.704, CHCl ₃ )
Melting point 168-169 [deg.] C.

Example 119
Preparation of (R) -4- (4-Chlorobenzyl) piperazine-1-carboxylic acid 2-methyl 6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl ester Example 90 (R) -4- (4-chlorobenzyl) piperazine-1-carboxylic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester (1. Sodium hydride (0.31 g, 7.70 mmol) was added to a solution of 82 g (3.85 mmol) in DMF (10 ml) with ice cooling, and the mixture was further stirred at 0 ° C. for 1 hour. Ice water is added to the reaction solution, the precipitate is collected by filtration, the crude crystals are washed with isopropanol, and (R) -4- (4-chlorobenzyl) piperazine-1-carboxylic acid 2-methyl 6-nitro as a slightly yellow solid. There was obtained (0.46 g, 28% yield) of -2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl ester.
Mp 161-163 ° C.

Example 120
(R) -4- (4-Trifluoromethylbenzylideneamino) piperazine-1-carboxylic acid 2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl ester Preparation (R) -4- (4-Trifluoromethylbenzylideneamino) piperazine-1-carboxylic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2 prepared in Example 103 Sodium hydride (0.37 g, 9.32 mmol) was added to a solution of methylpropyl ester (4.03 g, 7.77 mmol) in DMF (20 ml) with ice cooling and stirring, and the mixture was stirred at 0 ° C for 1 hour. Ice water is added to the reaction solution, the precipitate is collected by filtration, washed with water, recrystallized from acetonitrile and isopropanol, and (R) -4- (4-trifluoromethylbenzylideneamino) piperazine-1-carboxylic acid as a white solid. 2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl ester (2.60 g, 69% yield) was obtained.
Melting point 176-178 [deg.] C.

Example 121
(R) -4- (4-Trifluoromethylphenylamino) piperidine-1-carboxylic acid 2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl ester Preparation (R) -4- (4-Trifluoromethylphenylamino) piperidine-1-carboxylic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2 prepared in Example 105 Sodium hydride (0.14 g, 3.42 mmol) was added to a solution of -methylpropyl ester (1.44 g, 2.85 mmol) in DMF (10 ml) with ice cooling and further stirred at 0 ° C for 1 hour . Ice water is added to the reaction mixture, and the mixture is extracted with ethyl acetate, washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (ethyl acetate), recrystallized from acetonitrile and isopropanol, and white solid of (R) -4- (4-trifluoromethylphenylamino) piperidine-1-carboxylic acid 2-methyl- There was obtained 6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl ester (0.42 g, 31% yield).
Melting point 137-140 [deg.] C.

Example 122
Preparation of (R) -4- (4-trifluoromethylphenoxy) piperidine-1-carboxylic acid 2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl ester (R) -4- (4-Trifluoromethylphenoxy) piperidine-1-carboxylic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methyl prepared according to Example 104 Sodium hydride (19 mg, 0.47 mmol) was added to a solution of propyl ester (0.18 g, 0.36 mmol) in DMF (2 ml) with ice cooling, and the mixture was further stirred at 0 ° C. for 1.5 hours. Ice water was added to the reaction solution, extracted with ethyl acetate, washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 9/1), recrystallized from isopropanol, and (R) -4- (4-trifluoromethylphenoxy) piperidine-1-carboxylic acid as a white solid 2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl ester (0.08 g, 47% yield) was obtained.
Mp 165-166 ° C.

Example 123
(R) -4- (4-trifluoromethylphenyl) -1,2,3,6-tetrahydropyridine-1-carboxylic acid 2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b Preparation of Oxazol-2-ylmethyl Ester (R) -4- (4-Trifluoromethylphenyl) -1,2,3,6-tetrahydropyridine-1-carboxylic acid 3- (2) prepared in Example 106 Sodium hydride (31 mg) under ice cooling with a solution of -chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester (0.32 g, 0.65 mmol) in DMF (3 ml). 0.78 mmol) was added, and the mixture was further stirred at 0 ° C. for 1.5 hours. Ice water is added to the reaction mixture, and the mixture is extracted with ethyl acetate, washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 9/1) and recrystallized from isopropanol to give (R) -4- (4-trifluoromethylphenyl) -1,2,3 as a white solid. 6,6-Tetrahydropyridine-1-carboxylic acid 2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl ester (0.14 g, yield 49%) is obtained The
Optical purity 98.4% ee
^{_{[Α] D 26 = + 2.50}} ° (c0.560, CHCl 3).
Mp 169-171 ° C.

Example 124
Preparation of (R) -5-Chloro-2,3-dihydroindole-1-carboxylic acid 2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl ester (R) -5-Chloro-2,3-dihydroindole-1-carboxylic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl ester prepared in Example 113 Sodium hydride (70 mg, 1.73 mmol) was added to a solution of (0.60 g, 1.44 mmol) in DMF (6 ml) with stirring under ice cooling, and the mixture was further stirred at 0 ° C. for 1 hour. Ice water was added to the reaction solution, and the precipitate was collected by filtration and washed with water. This is recrystallized from acetonitrile and isopropanol, and (R) -5-chloro-2,3-dihydroindole-1-carboxylic acid 2-methyl-6-nitro-2,3-dihydroimidazo [2,1] as a white solid -B] oxazol-2-ylmethyl ester (0.30 g, 55% yield) was obtained.
Melting point 189-191 [deg.] C.

Example 125
Preparation of (R) -5-Chloro-1,3-dihydroisoindole-2-carboxylic acid 2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl ester (R) -5-Chloro-1,3-dihydro-isoindole-2-carboxylic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2- 2 Sodium hydride (15 mg, 0.37 mmol) was added to a solution of methyl propyl ester (0.13 g, 0.31 mmol) in DMF (2 ml) with ice cooling, and the mixture was further stirred at 0 ° C. for 1 hour. Ice water is added to the reaction mixture, and the mixture is extracted with ethyl acetate, washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate), and a slightly yellow solid of (R) -5-chloro-1,3-dihydroisoindole-2-carboxylic acid 2-methyl-6-nitro-2,3- Dihydroimidazo [2,1-b] oxazol-2-ylmethyl ester (7 mg, 6% yield) was obtained.
Melting point 182 [deg.] C (decomposition).

Example 126
(R) -6-Chloro-3,4-dihydro-1H-isoquinoline-2-carboxylic acid 2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl ester Preparation of (R) -6-Chloro-3,4-dihydro-1H-isoquinoline-2-carboxylic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy prepared in Example 115 Sodium hydride (30 mg, 0.73 mmol) was added to a solution of -2-methylpropyl ester (0.26 g, 0.61 mmol) in DMF (2 ml) with ice cooling and further stirred at 0 ° C. for 1 hour . Ice water is added, and the mixture is extracted with ethyl acetate, washed with water, dried over magnesium sulfate and concentrated under reduced pressure. It is recrystallized from isopropanol and (R) -6-chloro-3,4-dihydro-1H-isoquinoline-2-carboxylic acid 2-methyl-6-nitro-2,3-dihydroimidazo [2, 1] as a slightly yellow solid. -B] Oxazol-2-ylmethyl ester (0.12 g, 49%) was obtained.
Mp 180-182 ° C.

Example 127
(R) -6-chloro-3,4-dihydro-2H-quinoline-1-carboxylic acid 2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl ester Preparation of (R) -6-Chloro-3,4-dihydro-2H-quinoline-1-carboxylic acid 3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy prepared in Example 116 Sodium hydride (0.21 g, 5.15 mmol) was added to a solution of -2-methylpropyl ester (1.84 g, 4.29 mmol) in DMF (10 ml) with ice-cooling and stirring, and further at 0 ° C. for 1 hour It stirred. Ice water is added to the reaction mixture, and the mixture is extracted with ethyl acetate, washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 9/1), recrystallized from acetonitrile and isopropanol, and (R) -6-chloro-3,4-dihydro-2H-quinoline as a white solid. 1-carboxylic acid 2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl ester (0.68 g, 40% yield) was obtained.
Melting point 172-174 [deg.] C.

Example 128
Preparation of 2-Methyl-6-nitro-2- (4-trifluoromethoxyphenoxymethyl) -2,3-dihydroimidazo [2,1-b] oxazole 4-trifluoromethoxyphenol (198 mg, 1.11 mmol) Was dissolved in DMF (5 ml). To this solution was added sodium hydride (48 mg, 1.21 mmol) at room temperature, and the mixture was heated and stirred for 20 minutes while raising the temperature to 80 ° C. This is ice-cooled, 2-chloro-1- (2-methyloxiranylmethyl) -4-nitroimidazole (220 mg, 1.01 mmol) prepared in Example 6 is added, and the temperature is raised to 80 ° C. The mixture was further heated and stirred for 15 minutes. The reaction solution was poured into ice water and extracted with ethyl acetate. It was washed with saturated brine, dried over magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue is separated and purified by silica gel column chromatography (methylene chloride / ethyl acetate = 10/1), further crystallized by methylene chloride-diisopropyl ether, filtered and dried under reduced pressure to obtain 2-methyl-6 of white powder. -Nitro-2- (4-trifluoromethoxyphenoxymethyl) -2,3-dihydroimidazo [2, l-b] oxazole (170 mg, yield 47%) was obtained.
Melting point 126.8-127.9 ° C
MS 358 (M-1) ⁺
Example 129
Preparation of 2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethoxyphenoxy) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole 4- [4- (4-Trifluoromethoxyphenoxy) piperidine] -1-ylphenol (244 mg, 0.69 mmol) was dissolved in DMF (10 ml). To this solution was added sodium hydride (33 mg, 0.83 mmol) at room temperature, and the mixture was heated and stirred for 20 minutes while raising the temperature to 80 ° C. This is ice-cooled, 2-chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitroimidazole (150 mg, 0.69 mmol) prepared in Example 6 is added, and the temperature is raised to 80 ° C. The mixture was heated and stirred for another 20 minutes while warming. Ice water was added to the reaction solution, the mixture was vigorously stirred, the precipitate was collected by filtration and washed with water. This was dissolved in methylene chloride, washed with saturated brine, dried over magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue is separated and purified by silica gel column chromatography (methylene chloride / ethyl acetate = 10/1) and further crystallized by methylene chloride / ethyl acetate to give 2-methyl-6-nitro-2- {4- [4] as a white powder. -(4-Trifluoromethoxyphenoxy) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole (103 mg, yield 28%) was obtained.
Mp 165.4-166.3 ° C.

Example 130
Preparation of 2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethylphenyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole 4- [4- (4-Trifluoromethylphenyl) piperazin-1-yl] phenol (296 mg, 0.92 mmol) was dissolved in DMF (10 ml). To this solution was added sodium hydride (44 mg, 1.1 mmol) at room temperature, and the mixture was heated and stirred for 20 minutes while raising the temperature to 80 ° C. This is ice-cooled, 2-chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitroimidazole (200 mg, 0.92 mmol) prepared in Example 6 is added, and the temperature is raised to 80 ° C. The mixture was heated and stirred for another 20 minutes while warming. Ice water was added to the reaction solution, the mixture was vigorously stirred, the precipitate was collected by filtration and washed with water. This was dissolved in methylene chloride, washed with saturated brine, dried over magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue is separated and purified by silica gel column chromatography (methylene chloride / ethyl acetate = 10/1) and further crystallized by methylene chloride / ethyl acetate to give 2-methyl-6-nitro-2- {4- [4] as a white powder. -(4-Trifluoromethylphenyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole (178 mg, yield 38%) was obtained.
Mp 230.7-233.1 ° C.

Example 131
Preparation of 4- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) phenyl] piperazine-1-carboxylic acid tert-butyl ester 4- (4- (2-methyl-6-nitro-2,3-dihydroimidazo) 4-hydroxyphenyl) piperazine-1-carboxylic acid tert-butyl ester (2.01 g, 7.23 mmol) was dissolved in DMF (20 ml). To this solution was added sodium hydride (320 mg, 8 mmol) at room temperature, and the mixture was heated and stirred for 20 minutes while raising the temperature to 70 ° C. This is ice-cooled, 2-chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitroimidazole (1.5 g, 7.23 mmol) prepared in Example 6 is added, and the mixture is heated to 80 ° C. The mixture was further heated and stirred for 20 minutes while raising the temperature. Ice water was added to the reaction solution, the mixture was vigorously stirred, the precipitate was collected by filtration and washed with water. This was dissolved in methylene chloride, washed with saturated brine, dried over magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue is separated and purified by silica gel column chromatography (methylene chloride / ethyl acetate = 20/1), further crystallized by methylene chloride-ethyl acetate, filtered and dried under reduced pressure to obtain 4- [4- [4] of white powder. (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) phenyl] piperazine-1-carboxylic acid tert-butyl ester (1.5 g, yield 45%) I got
¹ H-NMR (CDCl ₃ ) δ ppm:
1.48 (9 H, s), 1.77 (3 H, s), 2.99-3.03 (4 H, m), 3.55-3.59 (4 H, m), 4.02 (1 H, 1 H, s) d, J = 10.2 Hz), 4.04 (1 H, d, J = 10.1 Hz), 4.18 (1 H, d, J = 10.1 Hz), 4.49 (1 H, d, J = 10 .2 Hz), 6.76-6.81 (2H, m), 6.84-6.89 (2H, m), 7.55 (1 H, s).
Melting point 212.0-214.5 ° C
MS 459 (M ^<+> ).

Example 132
Preparation of 4- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) phenyl] piperidine-1-carboxylic acid tert-butyl ester 4- (4-) 4-hydroxyphenyl) piperidine-1-carboxylic acid tert-butyl ester (364 mg, 1.31 mmol) was dissolved in DMF (10 ml). To this solution was added sodium hydride (58 mg, 1.44 mmol) at room temperature, and the mixture was heated and stirred for 20 minutes while raising the temperature to 80 ° C. This is ice-cooled, 2-chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitroimidazole (300 mg, 1.38 mmol) prepared in Example 6 is added, and the temperature is raised to 80 ° C. The mixture was heated and stirred for another 20 minutes while warming. Ice water was added to the reaction solution, the mixture was vigorously stirred, the precipitate was collected by filtration and washed with water. This was dissolved in methylene chloride, washed with saturated brine, dried over magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue is separated and purified by silica gel column chromatography (methylene chloride / methanol = 200/1) and further crystallized by methylene chloride / diisopropyl ether to give 4- [4- (2-methyl-6-nitro-2) as a white powder. 3, 3-Dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) phenyl] piperidine-1-carboxylic acid tert-butyl ester (248 mg, yield 41%) was obtained.
Mp 207.8-209.1 ° C.

Example 133
Preparation of 4- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) phenyl] piperazine-1-carboxylic acid 3,4-dichlorobenzyl ester 4- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) phenyl] piperazine-1-carboxylate prepared in Example 131 tert-Butyl 1-carboxylate The ester (118 mg, 0.26 mmol) was dissolved in 5 ml of methylene chloride and trifluoroacetic acid (5 ml) was added and stirred for 3 hours at room temperature. The reaction solution was concentrated under reduced pressure, and 2 ml each of methylene chloride and triethylamine were added. The reaction solution was stirred at room temperature for 5 minutes, concentrated under reduced pressure, and the residue was dissolved in DMF (15 ml). Prepared by dissolving 3,4-dichlorobenzyl alcohol (136 mg, 0.77 mmol) and 1,1'-carbonyldiimidazole (125 mg, 0.77 mmol) in DMF (5 ml) and stirring for 3 hours at room temperature. The added solution was added and stirred at room temperature overnight. The reaction solution is poured into water and extracted with ethyl acetate, and the organic phase is washed with saturated brine, dried over magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (methylene chloride / methanol = 200/1). Crystallization from methylene chloride-isopropyl ether, filtration and drying under reduced pressure give 4- [4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] as a slightly yellow powder. ] Oxazol-2-ylmethoxy) phenyl] piperazine-1-carboxylic acid 3,4-dichlorobenzyl ester (101 mg, 70% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.77 (3H, s), 3.01 to 3.06 (4H, m), 3.62 to 3.67 (4H, m), 4.02 (1 H, d, J = 10.2 Hz), 4.04 (1H, d, J = 10.2 Hz), 4.18 (1 H, d, J = 10.2 Hz), 4.49 (1 H, d, J = 10.2 Hz), 5.09 (2 H) , S), 6.76-6.81 (2H, m), 6.84-6.89 (2H, m), 7.18-7. 22 (1 H, m), 7.41-7.47 (2H, m), 7.55 (1 H, s).

Example 134
Preparation of 2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethylbenzyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole 4- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) phenyl] piperazine-1-carboxylate prepared in Example 131 tert-Butyl 1-carboxylate The ester (88 mg, 0.19 mmol) was dissolved in trifluoroacetic acid (5 ml) and stirred for 5 hours at room temperature. The reaction solution was concentrated under reduced pressure, and 2 ml each of methylene chloride and triethylamine were added. After stirring for 5 minutes at room temperature, the solution was concentrated under reduced pressure. The residue is dissolved in dichloroethane, 4-trifluoromethylbenzaldehyde (40 μl, 0.29 mmol) and sodium triacetoxyborohydride (82 mg, 0.38 mmol) are added under ice-cooling, and the temperature is raised to room temperature and then overnight. It stirred. Saturated sodium hydrogencarbonate aqueous solution and methylene chloride were added to this, it stirred, and the methylene chloride extracted. The organic phase was dried over magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (methylene chloride / methanol = 200/1). Crystallization is carried out from methylene chloride-ethyl acetate, followed by filtration and drying under reduced pressure to obtain 2-methyl-6-nitro-2- {4- [4- (4-trifluoromethylbenzyl) piperazine-1 as a white powder. -Yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole (53 mg, 53% yield) was obtained.
Melting point 171.8-173.1 ° C.

  4- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) phenyl] piperidine-1-carboxylic acid tert-butyl ester prepared in Example 132 The compound of Example 135 was produced in the same manner as Example 134 using an ester.

Example 135
2-Methyl-6-nitro-2- {4- [1- (4-trifluoromethoxybenzyl) piperidin-4-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole yield 45%, mp 160.6-161.1 ° C.

Example 136
Preparation of (R) -2-Methyl-6-nitro-2- (4-trifluoromethoxyphenoxymethyl) -2,3-dihydroimidazo [2,1-b] oxazole 4-trifluoromethoxyphenol (1.1 g , 6.17 mmol) was dissolved in DMF (20 ml). To this solution was added sodium hydride (260 mg, 6.45 mmol) at room temperature, and the mixture was heated and stirred for 15 minutes while raising the temperature to 80 ° C. This was ice-cooled, and (R) -2-chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitroimidazole (1.22 g, 5.61 mmol) prepared in Example 12 was obtained. In addition, the mixture was heated and stirred for 2 hours while raising the temperature to 80 ° C. The reaction solution was poured into ice water and vigorously stirred, and then the precipitate was collected by filtration and washed with water. This was dissolved in methylene chloride, washed with saturated brine, dried over magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue is separated and purified by silica gel column chromatography (methylene chloride / ethyl acetate = 10/1), further crystallized by methylene chloride-diisopropyl ether, filtered and dried under reduced pressure to obtain white powder (R) -2 There was obtained -methyl-6-nitro-2- (4-trifluoromethoxyphenoxymethyl) -2,3-dihydroimidazo [2,1-b] oxazole (1.03 g, yield 51%).
Optical purity> 99% ee
[Α] _D ²⁸ = 7.67 ° (concentration: 1.030, CHCl ₃ )
MS 359 (M ⁺ )
Mp 176.5-178.0 ° C.

  The compounds of Example 137 to Example 139 were produced in the same manner as in Example 136, using the corresponding starting materials.

Example 137
(R) -2-Methyl-6-nitro-2- [4- (thiomorpholin-4-yl) phenoxymethyl] -2,3-dihydroimidazo [2,1-b] oxazole yield 38%, melting point 227 5-229.0 ° C., MS 376 (M ⁺ ).

Example 138
(R) -2-Methyl-6-nitro-2- [4- (imidazol-1-yl) phenoxymethyl] -2,3-dihydroimidazo [2,1-b] oxazole yield 44%, melting point 172- 175 ° C.

Example 139
(R) -2-Methyl-6-nitro-2- [4- (1,2,4-triazol-1-yl) phenoxymethyl] -2,3-dihydroimidazo [2,1-b] oxazole yield 53%, mp 236.0-238.7 ° C.

  The compound of Example 140 was produced in the same manner as Example 136 using 1- (4-hydroxyphenyl) piperidine-4-carboxylic acid ethyl ester.

Example 140
(R) -1- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) phenyl] piperidine-4-carboxylic acid ethyl ester yield 30 %, Mp 208.2-211.5 ° C.

Example 141
(R) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethoxyphenoxy) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b Preparation of oxazole 4- [4- (4-Trifluoromethoxyphenoxy) piperidin-1-yl] phenol (17.4 g, 49.0 mmol) was dissolved in DMF (150 ml). To the reaction mixture was added sodium hydride (2.15 g, 53.8 mmol) at room temperature, and the mixture was heated and stirred for 20 minutes while raising the temperature to 80 ° C. This was ice-cooled, and (R) -2-chloro-1- (2-methyloxiranylmethyl) -4-nitroimidazole (14.9 g, 68.6 mmol) prepared in Example 12 was added, The mixture was further heated and stirred for 20 minutes while raising the temperature to ° C. Ice water was added to the reaction solution, the mixture was vigorously stirred, the precipitate was collected by filtration and washed with water. This was dissolved in methylene chloride, washed with saturated brine, dried over magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue is separated and purified by silica gel column chromatography (methylene chloride / ethyl acetate = 10/1) and further crystallized by methylene chloride / ethyl acetate to obtain (R) -2-methyl-6-nitro-2- as a pale yellow powder. {4- [4- (4-Trifluoromethoxyphenoxy) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole (14.3 g, yield 55%) is obtained. The
MS 535 (M + 1) ⁺
Optical purity 99.9% ee
[Α] _D ²⁸ = -9.94 ° (concentration: 1.006, CHCl ₃ )
Melting point 194.5-196 ° C
¹ H-NMR (CDCl ₃ ) δ ppm:
1.77 (3 H, s), 1.87-2.00 (2 H, m), 2.05-2.16 (2 H, m), 2.95-3.05 (2 H, m), 3. 32-3.41 (2H, m), 4.02 (1H, d, J = 10.2 Hz), 4.04 (1H, d, J = 10.2 Hz), 4.18 (1H, d, J = 10.2 Hz), 4.36-4.45 (1H, m), 4.49 (1H, d, J = 10.2 Hz), 6.74-6.81 (2H, m), 6.87 -6.94 (4H, m), 7.11-7.16 (2H, m), 7.55 (1 H, s).

Example 142
(R) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethoxyphenyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b Preparation of oxazole 4- [4- (4-Trifluoromethoxyphenyl) piperazin-1-yl] phenol (1.7 g, 5.02 mmol) was dissolved in DMF (20 ml). To this solution was added sodium hydride (221 m, 5.53 mmol) at room temperature, and the mixture was heated and stirred for 20 minutes while raising the temperature to 80 ° C. This was ice-cooled, and (R) -2-chloro-1- (2-methyloxiranylmethyl) -4-nitroimidazole (1.2 g, 5.53 mmol) prepared in Example 12 was added, The mixture was further heated and stirred for 20 minutes while raising the temperature to ° C. Ice water was added to the reaction solution, the mixture was vigorously stirred, the precipitate was collected by filtration and washed with water. This was dissolved in methylene chloride, washed with saturated brine, dried over magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue is separated and purified by silica gel column chromatography (methylene chloride / ethyl acetate = 10/1) and further recrystallized from ethyl acetate to give pale yellow powder of (R) -2-methyl-6-nitro-2- { 4- [4- (4-trifluoromethoxyphenyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole (1.02 g, yield 39%) was obtained .
MS 519 (M ⁺ )
Optical purity> 99% ee
[Α] _D ²⁸ = -18.02 ° (concentration: 1.160, CHCl ₃ )
Mp 262.5-265 ° C.

Example 143
(R) -4- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) phenyl] piperidine-1-carboxylic acid tert-butyl ester Preparation 4- (4-hydroxyphenyl) piperidine-1-carboxylic acid tert-butyl ester (1.07 g, 3.86 mmol) was dissolved in 10 ml DMF. To this solution was added sodium hydride (185 mg, 4.63 mmol) at room temperature, and the mixture was heated and stirred for 20 minutes while raising the temperature to 80 ° C. This was ice-cooled, 923 mg (4.24 mmol) of (R) -2-chloro-1- (2-methyloxiranylmethyl) -4-nitroimidazole prepared in Example 12 was added, and the temperature was raised to 80 ° C. The mixture was heated and stirred for another 20 minutes while warming. Ice water was added to the reaction solution, the mixture was vigorously stirred, the precipitate was collected by filtration and washed with water. This was dissolved in methylene chloride, washed with saturated brine, dried over magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (methylene chloride / methanol = 200/1), and further crystallized from ethyl acetate / diisopropyl ether to give (R) -4- [4- (2-methyl-6-) as a white powder. Nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) phenyl] piperidine-1-carboxylic acid tert-butyl ester (857 mg, yield 48%) was obtained.
MS 458 (M ⁺ )
Optical purity> 99% ee
[Α] _D ²⁸ = -1.07 ° (concentration: 1.028, CHCl ₃ )
Melting point 227.5-228.3 ° C (decomposition).

  The compound of Example 144 was produced in the same manner as in Example 143, using the corresponding starting materials.

Example 144
(R) -4- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) phenyl] -1,2,3,6-tetrahydropyridine -1-carboxylic acid tert-butyl ester MS 438 (M-18) ⁺
Melting point 183.0-189.0 ° C (decomposition).

Example 145
(R) -4- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) benzoyl] piperazine-1-carboxylic acid tert-butyl ester Preparation 4- (4-hydroxybenzoyl) piperazine-1-carboxylic acid tert-butyl ester (6.6 g, 21.5 mmol) was dissolved in 50 ml DMF. To this solution was added sodium hydride (991 mg, 24.8 mmol) at room temperature, and the mixture was heated and stirred for 20 minutes while raising the temperature to 80 ° C. This was ice-cooled, and (R) -2-chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitroimidazole 5.16 (23.7 mmol) prepared in Example 12 was added. The mixture was further heated and stirred for 20 minutes while raising the temperature to 80 ° C. Ice water was added to the reaction solution, the mixture was vigorously stirred, the precipitate was collected by filtration and washed with water. This was dissolved in methylene chloride, washed with saturated brine, dried over magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue is separated and purified by silica gel column chromatography (methylene chloride / methanol = 100/1), and further crystallized from methylene chloride / diisopropyl ether to give (R) -4- [4- (2-methyl-6-) as a white powder. Nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) benzoyl] piperazine-1-carboxylic acid tert-butyl ester (7.35 g, 70% yield) was obtained.
MS 488 (M + 1) ⁺
Melting point 222.5-224.0 [deg.] C.

Example 146
(R) -4- [2-Chloro-4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) phenyl] piperazine-1-carboxylic acid tert Preparation of -butyl ester 4- (2-Chloro-4-hydroxyphenyl) piperazine-1-carboxylic acid tert-butyl ester (2.7 g, 8.63 mmol) was dissolved in 20 ml DMF. To this solution was added sodium hydride (397 mg, 9.92 mmol) at room temperature, and the mixture was heated and stirred for 20 minutes while raising the temperature to 80 ° C. This was ice-cooled, and (R) -2-chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitroimidazole (2.1 g, 9.50 mmol) prepared in Example 12 was obtained. In addition, the mixture was heated and stirred for 20 minutes while raising the temperature to 80 ° C. Ice water was added to the reaction solution, the mixture was vigorously stirred, the precipitate was collected by filtration and washed with water. This was dissolved in methylene chloride, washed with saturated brine, dried over magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue is separated and purified by silica gel column chromatography (methylene chloride / methanol = 200/1), and further crystallized by methylene chloride / ethyl acetate to obtain (R) -4- [2-chloro-4- (2-) Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) phenyl] piperazine-1-carboxylic acid tert-butyl ester (2.34 g, 55% yield) was obtained .
MS 493 (M ⁺ )
Mp 207.0-209.5 ° C.

Example 147
(R) -4- [3- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) phenyl] piperazine-1-carboxylic acid tert-butyl ester Preparation 4- (3-hydroxyphenyl) piperazine-1-carboxylic acid tert-butyl ester (3.23 g, 11.6 mmol) was dissolved in 40 ml DMF. To this solution was added 557 mg (13.9 mmol) of sodium hydride at room temperature, and the mixture was heated and stirred for 20 minutes while raising the temperature to 70 ° C. This is ice-cooled, and 2.78 g (12.8 mmol) of (R) -2-chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitroimidazole prepared in Example 12 is added. The mixture was further heated and stirred for 20 minutes while raising the temperature to 80 ° C. Ice water was added to the reaction solution, the mixture was vigorously stirred, the precipitate was collected by filtration and washed with water. This was dissolved in methylene chloride, washed with saturated brine, dried over magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue is separated and purified by silica gel column chromatography (methylene chloride / methanol = 100/1), further crystallized by methylene chloride-ethyl acetate, filtered and dried under reduced pressure to obtain (R) -4 as a white powder. -[3- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) phenyl] piperazine-1-carboxylic acid tert-butyl ester (1.4 g, 26% rate).
MS 459 (M ⁺ )
Melting point 179.5-182.0 ° C.

Example 148
(R) -4- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) phenyl] piperazine-1-carboxylic acid tert-butyl ester Preparation 4- (4-hydroxyphenyl) piperazine-1-carboxylic acid tert-butyl ester (13.5 g, 48.8 mmol) was dissolved in 100 ml DMF. To this solution was added sodium hydride (2.15 g, 53.7 mmol) at room temperature, and the mixture was heated and stirred for 20 minutes while raising the temperature to 70 ° C. This was ice-cooled, and (R) -2-chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitroimidazole (10.6 g, 48.8 mmol) prepared in Example 12 was obtained. In addition, the mixture was heated and stirred for 20 minutes while raising the temperature to 80 ° C. Ice water was added to the reaction solution, the mixture was vigorously stirred, the precipitate was collected by filtration and washed with water. This was dissolved in methylene chloride, washed with saturated brine, dried over magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue is separated and purified by silica gel column chromatography (methylene chloride / methanol = 100/1), further crystallized by methylene chloride-ethyl acetate, filtered and dried under reduced pressure to obtain (R) -4 as a white powder. -[4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) phenyl] piperazine-1-carboxylic acid tert-butyl ester (9.9 g, The rate is 44%).
Optical purity> 99.5% ee
[Α] _D ²⁸ = -10.85 ° (concentration: 1.014, CHCl ₃ )
MS 459 (M ⁺ )
Melting point 230-232 ° C
¹ H-NMR (CDCl ₃ ) δ ppm:
1.48 (9 H, s), 1.76 (3 H, s), 2.99-3.03 (4 H, m), 3.54-3.59 (4 H, m), 4.02 (1 H, 1 H, d, J = 10.2 Hz), 4.04 (1 H, d, J = 10.1 Hz), 4.18 (1 H, d, J = 10.1 Hz), 4.49 (1 H, d, J = 10 .2 Hz), 6.76-6.81 (2H, m), 6.85-6.89 (2H, m), 7.58 (1 H, s).

Example 149
Preparation of (R)-[4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) phenyl] piperazine dihydrochloride Prepared as in Example 148 ( R) 4- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) phenyl] piperazine-1-carboxylic acid tert-butyl ester (300 mg , 0.65 mmol) was dissolved in 5 ml of trifluoroacetic acid and stirred for 3 hours at room temperature. The reaction solution was concentrated under reduced pressure, and the residue was dissolved in methanol. To this, 5 ml of saturated hydrogen chloride ethyl acetate solution is added, and the precipitate is collected by filtration and dried under reduced pressure to obtain (R)-[4- (2-methyl-6-nitro-2,3-dihydro] as a pale yellow powder. Imidazo [2,1-b] oxazol-2-ylmethoxy) phenyl] piperazine dihydrochloride (279 mg, yield 99%) was obtained.
MS 359 (M ⁺ )
Melting point 212-220 ° C (decomposition)
¹ H-NMR (DMSO-d ₆ ) δ ppm:
1.67 (3 H, s), 3.22-3.31 (8 H, m), 4.18 (1 H, d, J = 10.9 Hz), 4.23 (2 H, s), 4.37 (4 1 H, d, J = 10.9 Hz), 6.85 (2 H, d, J = 9.1 Hz), 7.00 (2 H, d, J = 9.1 Hz), 8. 16 (1 H, s), 9.37 (3H, br).

Example 150
(R) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethylbenzyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b Preparation of Oxazole] (R) -4- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) phenyl] piperazine prepared in Example 148 A mixture of -1-carboxylic acid tert-butyl ester (800 mg, 1.74 mmol) and trifluoroacetic acid (3 ml) was stirred at room temperature for 7 hours. The reaction solution was concentrated under reduced pressure, the residue was dissolved in 10 ml of methylene chloride, 3 ml (21.52 mmol) of triethylamine was added, and the mixture was stirred at room temperature for 5 minutes and concentrated under reduced pressure. The residue is dissolved in 10 ml of methanol and 4-trifluoromethylbenzaldehyde (910 mg, 5.23 mmol), sodium cyanotrihydroborate (328 mg, 5.23 mmol) and 0.33 ml (5.23 mmol) of acetic acid under ice cooling. ) Was added, the mixture was warmed to room temperature and stirred overnight. Saturated aqueous sodium hydrogen carbonate solution and methylene chloride were added and the mixture was stirred and extracted with methylene chloride. The organic phase was dried over magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue is separated and purified by silica gel column chromatography (methylene chloride / methanol = 200/1) to give (R) -2-methyl-6-nitro-2- {4- [4- (4- (4-) Trifluoromethylbenzyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole (667 mg, yield 74%) was obtained.
Mp 205.5-207 ° C.

Example 151
Preparation of (R) -4- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) phenyl] piperazine-1-carboxylic acid ethyl ester (R) -4- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) phenyl] piperazine-1-carboxylic acid prepared in Example 148 The tert-butyl ester (300 mg, 0.65 mmol) was dissolved in 5 ml of methylene chloride, 5 ml of trifluoroacetic acid were added and stirred for 3 hours at room temperature. The reaction solution was concentrated under reduced pressure, 5 ml of methylene chloride and 2 ml of triethylamine were added, followed by addition of ethyl chloroformate (0.11 ml, 1.31 mmol), and the mixture was stirred at room temperature for 1 hour. The reaction solution was poured into water, extracted with methylene chloride, and the organic phase was washed with saturated brine. After drying over magnesium sulfate, it was filtered. The resulting filtrate was concentrated under reduced pressure. The residue is separated and purified by silica gel column chromatography (methylene chloride / methanol = 200/1), crystallized from methylene chloride-isopropyl ether, filtered and dried under reduced pressure to obtain white powder (R) -4. -[4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) phenyl] piperazine-1-carboxylic acid ethyl ester (182 mg, 65% yield) I got
^{_{[Α] D 28 = -9.86 °}} ( concentration: 1.014, CHCl _3).
MS 431 (M ⁺ )
Mp 210.5-212.0 ° C.

Example 152
(R) -4- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) phenyl] piperazine-1-carboxylic acid 4-chlorobenzyl ester Preparation of (R) -4- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) phenyl] piperazine-1 prepared in Example 148 Carboxylic acid tert-butyl ester (300 mg, 0.65 mmol) was dissolved in 5 ml of methylene chloride, 5 ml of trifluoroacetic acid were added and stirred for 3 hours at room temperature. The reaction solution was concentrated under reduced pressure, and 2 ml each of methylene chloride and triethylamine were added. After stirring for 5 minutes at room temperature, the solution was concentrated under reduced pressure, and the residue was dissolved in 15 ml of DMF. A mixture of 4-chlorobenzyl alcohol (186 mg, 1.31 mmol) and 1,1'-carbonyldiimidazole (212 mg, 1.31 mmol) dissolved in 5 ml of DMF and stirred at room temperature for 3 hours was added thereto, and it was left overnight at room temperature. It stirred. The reaction mixture was poured into water, extracted with ethyl acetate, and the organic phase was washed with saturated brine. After drying over magnesium sulfate, it was filtered. The resulting filtrate was concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (methylene chloride / methanol = 200/1). Crystallization from methylene chloride-isopropyl ether, filtration and drying under reduced pressure give (R) -4- [4- (2-methyl-6-nitro-2,3-dihydroimidazo [2] as a slightly yellow powder. [1,1-b] oxazol-2-ylmethoxy) phenyl] piperazine-1-carboxylic acid 4-chlorobenzyl ester (313 mg, yield 91%) was obtained.
[Α] _D ²⁸ = -10.84 ° (concentration: 1.006, CHCl ₃ )
MS 527 (M ⁺ )
Mp 184.5-187.5 ° C.

  The compound of Example 153 was produced in the same manner as Example 152 using the corresponding starting materials.

Example 153
(R) -4- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) phenyl] piperazine-1-carboxylic acid 5-chlorobenzofuran- 2-yl methyl ester yield 79%, mp 195-197 ° C.

  (R) -4- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) phenyl] piperidine-1-carboxylic acid prepared in Example 143 Acid tert-butyl ester, (R) -4- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) phenyl prepared in Example 144 ] -1,2,3,6-Tetrahydropyridine-1-carboxylic acid tert-butyl ester, (R) -4- [4- (2-methyl-6-nitro-2,3-) prepared in Example 145 Dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) benzoyl] piperazine-1-carboxylic acid tert-butyl ester, or (R) -4- [3 prepared in Example 147 As in Example 152, using (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) phenyl] piperazine-1-carboxylic acid tert-butyl ester The compounds of Example 154 to Example 158 were produced.

Example 154
(R) -4- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) phenyl] piperidine-1-carboxylic acid 4-trifluoromethoxy Benzyl ester yield 54%, mp 202.5-204 ° C.

Example 155
(R) -4- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) phenyl] -1,2,3,6-tetrahydropyridine -1-carboxylic acid 4-trifluoromethoxybenzyl ester yield 67%, mp 174.3-174.8 ° C.

Example 156
(R) -4- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) benzoyl] piperazine-1-carboxylic acid 4-trifluoromethoxy Benzyl ester yield 86%, mp 168.5-172 ° C.

Example 157
(R) -4- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) benzoyl] piperazine-1-carboxylic acid ethyl ester yield 85 %, Mp 132-135 ° C.

Example 158
(R) -4- [3- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) phenyl] piperazine-1-carboxylic acid 4-trifluoromethoxy Benzyl ester yield 50%, mp 136.5-138 ° C.

Example 159
(R) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethoxybenzyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b Preparation of Oxazole] (R) -4- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) phenyl] piperazine prepared in Example 148 The 1-carboxylic acid tert-butyl ester (4.22 g, 9.60 mmol) was dissolved in 10 ml of methylene chloride, 30 ml of trifluoroacetic acid was added and the mixture was stirred at room temperature for 5 hours. The reaction solution was concentrated under reduced pressure, and 10 ml each of methylene chloride and triethylamine were added. The mixture was stirred at room temperature for 5 minutes and concentrated under reduced pressure. The residue is dissolved in dichloroethane, 4-trifluoromethoxybenzaldehyde (1.64 ml, 11.5 mmol) and sodium triacetoxyborohydride (3.05 g, 14.4 mmol) are added under ice-cooling, and the temperature is raised to room temperature. After warming, it was stirred overnight. Saturated sodium hydrogencarbonate aqueous solution and methylene chloride were added to this, it stirred, and the methylene chloride extracted. The organic phase was dried over magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (methylene chloride / methanol = 200/1). Crystallization from methylene chloride-ethyl acetate, filtration and drying under reduced pressure give (R) -2-methyl-6-nitro-2- {4- [4- (4-trifluoromethoxy) as a slightly yellow powder. Benzyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole (3.23 g, yield 63%) was obtained.
Optical purity> 99.5% ee
[Α] _D ²⁸ = -8.25 ° (concentration: 1.018, CHCl ₃ )
MS 533 (M ⁺ )
Mp 213.5-217 ° C.

  The compound of Example 159 was also prepared in Example 160 below.

Example 160
(R) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethoxybenzyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b Preparation of oxazole 3.36 g (9.54 mmol) of 4- [4- (4-trifluoromethoxybenzyl) piperazin-1-yl] phenol was dissolved in 20 ml of DMF. To this solution was added 420 mg (10.5 mmol) of sodium hydride at room temperature, and the mixture was heated and stirred for 15 minutes while raising the temperature to 80 ° C. This was ice-cooled, and 2.18 g (10.0 mmol) of (R) -2-chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitroimidazole prepared in Example 12 was added. The mixture was further heated and stirred for 15 minutes while raising the temperature to 80 ° C. Ice water was added to the reaction solution, the mixture was vigorously stirred, and the precipitate was collected by filtration and washed with water. This was dissolved in methylene chloride, washed with saturated brine, dried over magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue is separated and purified by silica gel column chromatography (methylene chloride / methanol = 100/1), further crystallized by methylene chloride-ethyl acetate, filtered and dried to obtain light yellow powder of (R) -2- Methyl-6-nitro-2- {4- [4- (4-trifluoromethoxybenzyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole (2.0 g) , Yield 40%).

  (R) -4- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) phenyl] piperidine-1-carboxylic acid prepared in Example 143 Acid tert-butyl ester, (R) -4- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) phenyl prepared in Example 144 ] -1,2,3,6-Tetrahydropyridine-1-carboxylic acid tert-butyl ester or (R) -4- [4- (2-methyl-6-nitro-2,3- 3 Example 1 in analogy to example 159 using dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) benzoyl] piperazine-1-carboxylic acid tert-butyl ester 1 were prepared compounds of Examples 163.

Example 161
(R) -2-Methyl-6-nitro-2- {4- [1- (4-trifluoromethoxybenzyl) piperidin-4-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b 45% yield, mp 186-188 ° C.

Example 162
(R) -2-Methyl-6-nitro-2- {4- [1- (4-trifluoromethoxybenzyl) -1,2,3,6-tetrahydro-2H-pyridin-4-yl] phenoxymethyl} 2,3-dihydroimidazo [2,1-b] oxazole yield 61%, mp 168-174 ° C.

Example 163
(R) -4- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) benzoyl] -1- (4-trifluoromethoxybenzyl) Piperazine yield 83%, mp 155-156 ° C.

Example 164
(R) -4- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) phenyl] piperazine-1-carboxylic acid 4-trifluoromethoxy Preparation of benzylamide (R) -4- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) phenyl] piperazine prepared in Example 148 The 1-carboxylic acid tert-butyl ester (120 mg, 0.26 mmol) was dissolved in 5 ml of methylene chloride, 5 ml of trifluoroacetic acid was added and the mixture was stirred at room temperature for 3 hours. The reaction solution was concentrated under reduced pressure, and 2 ml each of methylene chloride and triethylamine were added. The mixture was stirred at room temperature for 5 minutes, concentrated under reduced pressure, and the residue was dissolved in 10 ml of DMF. There, 4-trifluoromethoxybenzylamine (125 mg, 0.65 mmol) and 1,1'-carbonyldiimidazole (110 mg, 0.68 mmol) are dissolved in 5 ml of DMF, and the mixture stirred at room temperature for 3 hours is added. Stir at room temperature overnight. The reaction mixture is poured into water and extracted with ethyl acetate. The organic phase is washed with saturated brine, dried over magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (methylene chloride / methanol = 200/1). Crystallization from methylene chloride-isopropyl ether, filtration and drying under reduced pressure give (R) -4- [4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,2] as a white powder. 1-b] oxazol-2-ylmethoxy) phenyl) piperazine-1-carboxylic acid 4-trifluoromethoxybenzylamide (48 mg, 32% yield) was obtained.
MS 558 (M-18) ⁺
Mp 166.5-168.5 ° C.

Example 165
(R) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethoxybenzoyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b Preparation of Oxazole] (R) -4- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) phenyl] piperazine prepared in Example 148 The 1-carboxylic acid tert-butyl ester (300 mg, 0.65 mmol) was dissolved in 5 ml of methylene chloride, to which 5 ml of trifluoroacetic acid was added and stirred for 5 hours at room temperature. The reaction solution was concentrated under reduced pressure, 10 ml of methylene chloride and 2 ml of triethylamine were added, followed by addition of 4-trifluoromethoxybenzoyl chloride (0.15 ml, 0.98 mmol) and stirred at room temperature for 1 hour. The reaction solution was poured into water, extracted with methylene chloride, and the organic phase was washed with saturated brine. The extract was dried over magnesium sulfate and filtered, and the obtained filtrate was concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (methylene chloride / ethyl acetate = 10/1). Crystallization from methylene chloride-diisopropyl ether, filtration and drying under reduced pressure give (R) -2-methyl-6-nitro-2- {4- [4- (4-trifluoromethoxybenzoyl) as a white powder. ) Piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole (263 mg, yield 74%) was obtained.
MS 547 (M ⁺ )
Mp 201.5-203.2 ° C.

Example 166
Preparation of (R) -2-Methyl-6-nitro-2- [4- (1-oxothiomorpholin-4-yl) phenoxymethyl] -2,3-dihydroimidazo [2,1-b] oxazole Example (R) -2-Methyl-6-nitro-2- [4- (thiomorpholin-4-yl) phenoxymethyl] -2,3-dihydroimidazo [2,1-b] oxazole (85 mg, 0.23 mmol) was dissolved in 5 ml of methylene chloride. To this was added m-chloroperbenzoic acid (59 mg, 0.24 mmol) and stirred at room temperature for 20 minutes. The reaction mixture was diluted with methylene chloride, washed with aqueous sodium thiosulfate solution, saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue is crystallized with methylene chloride-isopropyl ether, collected by filtration and dried to give (R) -2-methyl-6-nitro-2- [4- (1-oxothiomorpholine-4-) as a white powder. Y) phenoxymethyl] -2,3-dihydroimidazo [2,1-b] oxazole (59 mg, yield 67%) was obtained.
MS 392 (M ⁺ )
Melting point 198-200 ° C.

Example 167
Preparation of N-Methyl-N- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -2- (4-trifluoromethoxyphenoxy) ethylamine Example 2-Chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitroimidazole prepared in 6 (84 mg, 0.39 mmol), N-methyl-2- (4-trifluoromethoxyphenoxy) A mixture of ethylamine (100 mg, 0.43 mmol) and DMF (1 ml) was stirred at 65-70 ° C. for 8 hours. The reaction solution was returned to room temperature, poured into water and extracted with ethyl acetate. The extract was washed with saturated brine, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride / ethyl acetate = 20/1) to give a yellow oil.

The yellow oil was dissolved in 1 ml DMF, sodium hydride (11 mg, 0.28 mmol) was added and stirred at room temperature for 1 hour. Ice water was added to the reaction solution and extracted with ethyl acetate. The organic phase was washed with brine, dried over magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 10/1), crystallized from methylene chloride-diisopropyl ether, and white powder N-methyl-N- (2-methyl-6-nitro- 2,3-Dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -2- (4-trifluoromethoxyphenoxy) ethylamine (34 mg, 21% yield) was obtained.
Mp 86.4-89.2 ° C.

Example 168
N-methyl-N- {2- [N-methyl- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) amino] ethyl} carbamic acid tert- Preparation of butyl ester 2-Chloro-4-nitro-1H-imidazole (5.97 g, 27.43 mmol), N-methyl- {2- [N-methyl- (2-methyl-2-oxiranylmethyl) A mixture of amino] ethyl} carbamic acid tert-butyl ester (10.53 g, 40.76 mmol), triethylamine (0.76 ml, 5.49 mmol) and 1-propanol (60 ml) was heated to reflux for 5 hours. The reaction solution was returned to room temperature and concentrated under reduced pressure. To the residue was added water, extracted with methylene chloride, washed with saturated brine, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride / methanol = 20/1) to give a yellow oil.

The yellow oil was dissolved in 200 ml 1,4-dioxane, sodium hydride (500 mg, 12.5 mmol) was added and heated to reflux overnight. The reaction solution was returned to room temperature and concentrated under reduced pressure. To the residue was added ice water, extracted with methylene chloride, washed with saturated brine, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / methanol = 20/1) to give white powdery crystals of N-methyl-N- {2- [N-methyl- (2-methyl-6-nitro-2,3 -Dihydroimidazo [2,1-b] oxazol-2-ylmethyl) amino] ethyl} carbamic acid tert-butyl ester (1.94 g, 13% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.45 (9 H, s), 1.58 (3 H, s), 2. 38 (3 H, s), 2.57-2.69 (3 H, m), 2.79 (3 H, s), 2 .89 (1H, d, J = 14.9 Hz), 3.15-3.25 (2H, bm), 3.85 (1H, d, J = 14.9 Hz), 4.33 (1H, br) , 7.52 (1 H, s).

Example 169
(S) -N-Methyl-N- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl)-[2- {4- [4- (tri) Preparation of Fluoromethyl) phenyl] piperazin-1-yl} ethyl] amine (R) -2-Chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitroimidazole prepared in Example 12 523 mg (2.41 mmol) and N-methyl-2- [4- (4-trifluoromethylphenyl) piperazin-1-yl] ethylamine (900 mg, 3.13 mmol) are added to 15 ml of DMF, and the mixture is heated to 70-80.degree. Stir for 5 hours. The reaction solution was returned to room temperature, poured into water and extracted with ethyl acetate. The extract was washed with saturated brine, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride / ethyl acetate = 20/1) to give a yellow oil.

The yellow oil was dissolved in 15 ml DMF, sodium hydride (115 mg, 2.89 mmol) was added and stirred at room temperature for 1 hour. Ice water was added to the reaction solution and extracted with ethyl acetate. The organic phase was washed with brine, dried over magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 10/1), and crystallization is performed from methylene chloride-diisopropyl ether to give (S) -N-methyl-N- (2-methyl-) as a white powder. 6-Nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -2- [4- (4-trifluoromethylphenyl) piperazin-1-yl] ethylamine (173 mg, yield 15 %) Got.
MS 468 (M ⁺ )
Melting point 148.0-150.5 ° C.

  The compounds of Example 170 to Example 177 were produced in the same manner as in Example 169, using the corresponding starting materials.

Example 170
(S) -N-Methyl-N- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -2- (4-trifluoromethylphenoxy) ethylamine White powder, 12% yield
MS 399 (M-H) ⁺
Melting point 123.0-126.0 ° C.

Example 171
(S) -N-Methyl-N- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -2- (4-trifluoromethoxyphenoxy) ethylamine White powder, 45% yield
MS 416 (M ⁺ )
112.5-115.0 ° C.

Example 172
(S) -N, N'-Dimethyl-N- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -N '-(4-trifluoro) Methylphenyl) -1,2-ethylenediamine white powder, yield 24%
MS 413 (M ⁺ )
Melting point 135.5-137.5 ° C.

Example 173
(S) -4- [2- (N-Methyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethylamino) ethyl] piperazine-1-carvone Acid tert-butyl ester white powder, 30% yield
MS 425 (M + H) ⁺
Melting point 149.5-151.8 ° C.

Example 174
(S) -N-benzyl-N- [2- (4-trifluoromethoxyphenoxy) ethyl] -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-yl Methylamine white powder, 25% yield
Mp 96.5-97 ° C.

Example 175
(S) -N-Methyl-N- [3- (4-trifluoromethoxyphenoxy) propyl] -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-yl Methylamine white powder, 50% yield
Mp 92-95 ° C.

Example 176
(S) -N-Methyl-N- [2- (4-chlorophenoxy) ethyl] -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethylamine White powder, 27% yield
Melting point 130.5-132 ° C.

Example 177
(S) -N-Methyl-N- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -2- [4- (4-trifluoromethyl) Phenoxy) piperidin-1-yl] ethylamine light tea powder, 26% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
1.58 (3 H, s), 1. 70-1. 85 (2 H, m), 1. 98 (2 H, br), 2. 37 (3 H, s), 2. 25-2.50 (4 H, s) m), 2.50-2.80 (5H, m), 2.90 (1H, d, J = 14.9 Hz), 3.85 (1H, d, J = 9.5 Hz), 4.37 (4) 1 H, m), 4.52 (1 H, d, J = 14.9 Hz), 7.42 (2 H, d, J = 8.7 Hz), 7.52 (1 H, s), 7.53 (2 H, 2 H, s) d, J = 8.7 Hz).

Example 178
Preparation of N- (2-Ethoxycarbonylphenyl) -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethylamine 2-Chloro-4-nitro-1H- 5. imidazole (891 mg, 6.04 mmol), 1- (2-methyl-2-oxiranylmethyl) -1 H-benzo [d] [1,3] oxazine-2,4-dione (1.41 g, 6. A mixture of 04 mmol), sodium acetate (545 mg, 6.64 mmol) and ethanol (10 ml) was heated to reflux for 10 hours. The reaction solution was returned to room temperature and concentrated under reduced pressure. The residue was added with water, extracted with methylene chloride, washed with saturated brine, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and the residue was dissolved in 20 ml of 1,4-dioxane, sodium hydride (219 mg, 5.48 mmol) was added and heated to reflux for 5 hours. The reaction solution was returned to room temperature and concentrated under reduced pressure. Ice water was added to the residue, and the precipitated crystals were collected by filtration. The resultant is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 20/1) to obtain N- (2-ethoxycarbonylphenyl) -2-methyl-6-nitro-2,3-dihydroimidazo [white powder]. 2,1-b] oxazol-2-ylmethylamine (1.15 g, 55% yield) was obtained.
Mp 162.5-163.2 ° C.

Example 179
Preparation of (S) -1- [2-hydroxy-3- (N-methyl-benzylamino) -2-methylpropyl] -2-chloro-4-nitroimidazole (R) -2-prepared as in Example 12 A mixture of chloro-1- (2-methyloxiranylmethyl) -4-nitroimidazole (500 mg, 2.3 mmol), N-methylbenzylamine (334 mg, 2.76 mmol) and DMF (2.5 ml) Stir at 60 ° C. for 9 hours. The reaction solution was cooled to room temperature, water was added, and the mixture was extracted twice with ethyl acetate. The organic phases were combined, washed three times with water, dried over sodium sulfate and filtered. The filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (n-hexane / ethyl acetate = 1/1) to give (S) -1- [2-hydroxy-3- (N-) as a yellow oil. Methyl-N-benzylamino) -2-methylpropyl] -2-chloro-4-nitroimidazole (712 mg, 91% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.13 (3 H, s), 2.37-2.57 (5 H, m), 3.51 (1 H, d, J = 12.9 Hz), 3.72 (1 H, d, J = 12.9 Hz) ), 3.85 (2H, s), 7.16-7.39 (5H, m), 7.87 (1 H, s).

  The compounds of Example 180 to Example 187 were produced in the same manner as in Example 179, using the corresponding starting materials.

Example 180
(S) -1- {2-hydroxy-3- [N-methyl- (3-chlorobenzyl)] amino-2-methyl} propyl-2-chloro-4-nitroimidazole yield 98%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.15 (3 H, s), 2.35-2.57 (5 H, m), 3.53 (1 H, d, J = 13.3 Hz), 3.67 (1 H, d, J = 13.3 Hz) ), 3.92 (2H, s), 7.10-7. 31 (4H, m), 7.95 (1 H, s).

Example 181
(S) -1- {2-hydroxy-3- (N-methyl-4-chlorobenzylamino) -2-methylpropyl] -2-chloro-4-nitroimidazole yield 86%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.13 (3 H, s), 2.33-2.59 (5 H, m), 3.53 (1 H, d, J = 13.2 Hz), 3.68 (1 H, d, J = 13.2 Hz) ), 3.92 (2H, s), 7.19 (2H, d, J = 8.4 Hz), 7.31 (2 H, d, J = 8.4 Hz), 7.96 (1 H, s).

Example 182
(S) -1- [2-hydroxy-3- (N-methyl-4-trifluoromethoxybenzylamino) -2-methylpropyl] -2-chloro-4-nitroimidazole yield 98%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.13 (3 H, s), 2.37 (3 H, s), 2.47 (1 H, d, J = 13.9 Hz), 2.58 (1 H, d, J = 13.9 Hz), 58 (1 H, d, J = 13.3 Hz), 3.72 (1 H, d, J = 13.3 Hz), 3.94 (2 H, s), 7.19 (2 H, d, J = 8.6 Hz ), 7.31 (2 H, d, J = 8.6 Hz), 7.99 (1 H, s).

Example 183
(S) -1- [2-hydroxy-3- (N-methyl-4-trifluoromethylbenzylamino) -2-methylpropyl] -2-chloro-4-nitroimidazole yield 100%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.15 (3 H, s), 2.38 (3 H, s), 2.50 (1 H, d, J = 13.9 Hz), 2.60 (1 H, d, J = 13.9 Hz), 3. 65 (1 H, d, J = 13.6 Hz), 3.79 (1 H, d, J = 13.6 Hz), 3.97 (2 H, s), 7.41 (2 H, d, J = 8.2 Hz ), 7.61 (2H, d, J = 8.2 Hz), 8.00 (1 H, s).

Example 184
(S) -1- [2-hydroxy-3- (N-methyl-4-methoxybenzylamino) -2-methylpropyl] -2-chloro-4-nitroimidazole yield 85%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.12 (3 H, s), 2.36-2.50 (5 H, m), 3. 45 (1 H, d, J = 12.8 Hz), 3.64 (1 H, d, J = 12.8 Hz) ), 3.80 (3H, s), 3.84 (2H, s), 6.84 (2H, dd, J = 1.9 Hz, 8.6 Hz), 7.13 (2 H, dd, J = 1) .9 Hz, 8.6 Hz), 7.89 (1 H, s).

Example 185
(S) -1- [2-hydroxy-3- (N-methyl-4-dimethylaminobenzylamino) -2-methylpropyl] -2-chloro-4-nitroimidazole yield 94%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.11 (3H, s), 2.34-2.47 (5H, m), 2.93 (s, 6H), 3.39 (1H, d, J = 12.8 Hz), 3.60 ( 1 H, d, J = 12.8 Hz), 3.81 (2 H, s), 6.65 (2 H, d, J = 8.7 Hz), 7.03 (2 H, d, J = 8.7 Hz), 7.87 (1 H, s).

Example 186
(S) -1- [2-hydroxy-3- (N-methyl-phenylamino) -2-methylpropyl] -2-chloro-4-nitroimidazole yield 92%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.24 (3 H, s), 3.06 (3 H, s), 3. 40 (2 H, s), 4.05 (1 H, d, J = 14.2 Hz), 4. 13 (1 H, d, J) J = 14.2 Hz), 6.74-6.89 (3 H, m), 7.17-7.34 (2 H, m), 8.04 (1 H, s).

Example 187
(S) -1- {2-hydroxy-3- (N-methyl-4-chlorophenylamino) -2-methylpropyl] -2-chloro-4-nitroimidazole yield 92%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.24 (3H, s), 3.04 (3H, s), 3.38 (2H, s), 4.08 (2H, s), 6.74 (2H, dd, J = 2.1 Hz, 7.2 Hz), 7.19 (2 H, dd, J = 2.1 Hz, 7.2 Hz), 8.02 (1 H, s).

Example 188
Preparation of (S) -2- (N-benzyl-N-methyl) aminomethyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole Prepared as in Example 179 (S ) -1- [2-Hydroxy-3- (N-methyl-benzylamino) -2-methylpropyl] -2-chloro-4-nitroimidazole (710 mg, 2.1 mmol) and DMF (2.1 ml) To the mixture was added sodium hydride (101 mg, 2.51 mmol) under ice cooling, and the mixture was stirred at the same temperature for 2 hours. 0.7 ml of ethyl acetate and 5 ml of water were sequentially added to the reaction solution, and the precipitated crystals were collected by filtration. This was dissolved in 10 ml of isopropyl alcohol under heating to reflux, 28 mg of activated carbon was added, and heating to reflux was continued for 20 minutes. After hot filtration, 3 ml of isopropyl ether is added to the filtrate, the mixture is allowed to stand, and the precipitated crystals are collected by filtration to obtain (S) -2- (N-benzyl-N-methyl) aminomethyl-2 as a yellow powder crystal. -Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole (248 mg, 39% yield) was obtained.
132.5-133 ° C.

  The compounds of Example 189 to Example 196 were produced in the same manner as in Example 188, using the corresponding starting materials.

Example 189
(S) -2- [N- (4-chlorobenzyl) -N-methylamino] methyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole yield 44%, Melting point 129-129.5 [deg.] C.

Example 190
(S) -2- [N- (3-chlorobenzyl) -N-methylamino] methyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole yield 65%, Mp 177.5-178.5 ° C.

Example 191
(S) -2- [N- (4-Trifluoromethoxybenzyl) -N-methylamino] methyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole yield 53 %, Mp 145-146 ° C.

Example 192
(S) -2- [N- (4-Trifluoromethylbenzyl) -N-methylamino] methyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole yield 49 %, Mp 130-132 ° C.

Example 193
(S) -2- [N- (4-methoxybenzyl) -N-methylamino] methyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole yield 59%, Melting point 144-147 [deg.] C.

Example 194
(S) -2- [N- (4-dimethylaminobenzyl) -N-methylamino] methyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole yield 47% Mp 168-169 ° C.

Example 195
(S) -2- (N-phenyl-N-methylamino) methyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole yield 55%, melting point 147-148 ° C. .

Example 196
(S) -2- [N- (4-Chlorophenyl) -N-methylamino] methyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole yield 34%, melting point 174-175 ° C.

Example 197
(S) -4- [2- (N-Methyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethylamino) ethyl] piperazine-1-carvone Preparation of acid 4-trifluoromethylbenzyl ester (S) -4- [2- (N-methyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] prepared in Example 173 ] Oxazol-2-ylmethylamino) ethyl] piperazine-1-carboxylic acid tert-butyl ester (300 mg, 0.71 mmol) was dissolved in 5 ml of methylene chloride, 5 ml of trifluoroacetic acid was added and stirred at room temperature for 3 hours . The reaction solution was concentrated under reduced pressure, and 2 ml each of methylene chloride and triethylamine were added. After stirring for 5 minutes at room temperature, the reaction solution was concentrated under reduced pressure, and the residue was dissolved in 15 ml of DMF. Thereto, a mixture of 4-trifluoromethylbenzyl alcohol (373 mg, 2.12 mmol) and 1,1'-carbonyldiimidazole (344 mg, 2.12 mmol) dissolved in 5 ml of DMF and stirred at room temperature for 3 hours is added, and room temperature is added. The mixture was stirred for 1 hour. The reaction mixture was poured into water, extracted with ethyl acetate, and the organic phase was washed with saturated brine. After drying over magnesium sulfate, it was filtered. The resulting filtrate was concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (methylene chloride / methanol = 50/1). Crystallization from methylene chloride-isopropyl ether, filtration and drying under reduced pressure give (S) -4- [2- (N-methyl-2-methyl-6-nitro-2,3-) as a white powder. Dihydroimidazo [2,1-b] oxazol-2-ylmethylamino) ethyl] piperazine-1-carboxylic acid 4-trifluoromethylbenzyl ester (196 mg, 53% yield) was obtained.
MS 509 (M-H ₂ O) ⁺
Mp 77.2-76.9 ° C.

Example 198
(S) -N-Methyl-N- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -2- [4- (4-trifluoromethyl) Preparation of Benzyl) piperazin 1-yl] ethylamine The (S) -4- [2- (N-methyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] prepared in Example 173 ] Oxazol-2-ylmethylamino) ethyl] piperazine-1-carboxylic acid tert-butyl ester (400 mg, 0.94 mmol) was dissolved in 5 ml of methylene chloride, 5 ml of trifluoroacetic acid was added and stirred for 5 hours at room temperature . The reaction solution was concentrated under reduced pressure, and 2 ml each of methylene chloride and triethylamine were added. After stirring for 5 minutes at room temperature, the solution was concentrated under reduced pressure. The residue is dissolved in 10 ml of methanol and 4- (trifluoromethyl) benzaldehyde (0.4 ml, 2.83 mmol), sodium cyanotrihydroborate (178 mg, 2.83 mmol) and 0.2 ml of acetic acid are added and it is brought to room temperature. The mixture was stirred for 30 minutes. Saturated aqueous sodium hydrogen carbonate solution and methylene chloride were added, stirred and extracted with methylene chloride. The organic phase was dried over magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (methylene chloride / methanol = 200/1). Crystallization from methylene chloride-isopropyl ether, filtration and drying under reduced pressure give (S) -N-methyl-N- (2-methyl-6-nitro-2,3-dihydroimidazo [2] as a white powder. 1,1-b] oxazol-2-ylmethyl) -2- [4- (4-trifluoromethylbenzyl) piperazin 1-yl] ethylamine (307 mg, yield 68%) was obtained.
MS 482 (M ⁺ )
Mp 102.0-104.5 ° C.

Example 199
Preparation of (6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) carbamic acid ethyl ester 2,4-dinitro-1H-imidazole (0.678 g, 3.92 mmol) and 2-Oxiranylmethylcarbamic acid phenyl ester (1.04 g, 5.87 mmol) was dissolved in 20 ml of ethanol, sodium acetate (0.386 g, 4.70 mmol) was added and heated to reflux overnight. It extracted by adding saturated sodium hydrogencarbonate aqueous solution and a methylene chloride. After drying over sodium sulfate and filtration, the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (methylene chloride / methanol = 50/1) and diisopropyl ether was added. The precipitate is collected by filtration and dried under reduced pressure to give (6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) carbamic acid ethyl ester (0.116 g) as a slightly brown solid. Yield 11.6%) was obtained.
¹ H-NMR (DMSO-d ₆ ) δ ppm:
1.15 (3 H, t, J = 7.1 Hz), 3.41-3.51 (2 H, m), 3.93-4. 11 (3 H, m), 4. 38 (1 H, dd, J = 8.6 Hz, 10.7 Hz), 5.31-5. 47 (1 H, m), 7.52 (1 H, br), 8.13 (1 H, s).

Example 200
Preparation of (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) carbamic acid benzyl ester 2,4-dinitro-1H-imidazole (3 g, 19 mmol) and Dissolve (2-methyl-2-oxiranylmethyl) carbamic acid benzyl ester (4.31 g, 19 mmol) in ethanol (20 ml) and add sodium acetate (1.56 g, 19.0 mmol) to 70 ° C. Stirred overnight. It extracted by adding saturated sodium hydrogencarbonate aqueous solution and a methylene chloride. After drying over sodium sulfate and filtration, the filtrate was concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (n-hexane / ethyl acetate = 1/1, methylene chloride / methanol = 50/1) and recrystallized from ethyl acetate-methylene chloride to give colorless solid (2 -Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) carbamic acid benzyl ester (0.298 g, yield 4.7%) was obtained.
Melting point 171.3-172.2 ° C
¹ H-NMR (DMSO-d ₆ ) δ ppm:
1.55 (3 H, s), 3.46 (2 H, d, J = 6.3 Hz), 4.06 (1 H, d, J = 1 1.0 Hz), 4. 25 (1 H, d, J = 11) .0 Hz), 5.03 (2 H, s), 7.19-7.41 (5 H, m), 7. 76 (1 H, t, J = 6.3 Hz), 8.13 (1 H, s).

Example 201
Preparation of 2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethylamine trifluoroacetate salt Prepared as in Example 200 (2-Methyl-6-nitro- A mixture of 2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) carbamic acid benzyl ester (190 mg, 0.57 mmol), trifluoroacetic acid (4 ml) and methylene chloride (5 ml) at room temperature Stir overnight. The reaction solution was concentrated under reduced pressure. Diethyl ether is added to the residue, and the precipitated crystals are collected by filtration to obtain a slightly yellow powder of 2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethylamine tri. The fluoroacetate salt (120 mg, yield 67%) was obtained.
¹ H-NMR (DMSO-d ₆ ) δ ppm:
1.35 (3 H, s), 3.23 (1 H, d, J = 9.6 Hz), 3.49 (1 H, d, J = 9.6 Hz), 3.82-3.98 (2 H, m) ), 7.98 (1 H, s), 12. 22 (1 H, s).

  The compounds of Example 202 to Example 204 were produced in the same manner as in Example 200, using the corresponding starting materials.

Example 202
N-Methyl- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) carbamic acid benzyl ester yield 14%, mp 150.3-151.6 ° C .

Example 203
(6-Nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) carbamic acid benzyl ester yield 11%
¹ H-NMR (DMSO-d ₆ ) δ ppm:
3.45-3.59 (2H, m), 4.07 (1H, dd, J = 6.6 Hz, 10.8 Hz), 4.39 (1 H, dd, J = 8.6 Hz, 10.8 Hz) , 5.04 (2H, s), 5.32-5.50 (1 H, m), 7.23-7.41 (5 H, m), 7.71 (1 H, br), 8.13 (1 H) , S).

Example 204
(6-Nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) carbamic acid tert-butyl ester yield 27%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.43 (9H, s), 3.65 (2H, dd, J = 4.3 Hz, 6.2 Hz), 4.20 (1 H, dd, 7.0 Hz, 10.5 Hz), 4.36 (1 H) , Dd, J = 8.6 Hz, 10.5 Hz), 5.20 (1 H, t, J = 6.2 Hz), 5.35-5. 48 (1 H, m), 7.56 (1 H, s) .

Example 205
Preparation of (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) carbamic acid 4-chlorobenzyl ester 2,4-dinitro-1H-imidazole (0.518 g , 3.28 mmol) and (2-methyl-2-oxiranylmethyl) carbamic acid 4-chlorobenzyl ester (2.097 g, 8.20 mmol) were mixed and stirred at room temperature overnight. 6 ml of ethanol was added to the reaction solution, sodium acetate (0.538 g, 6.56 mmol) was added and the mixture was heated to reflux for 1 hour. Water was added to this and the precipitate was collected by filtration. The resulting solid is washed with diethyl ether and then dried under reduced pressure to give (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) carbamic acid as a colorless solid. -Chlorobenzyl ester (0.197 g, 16% yield) was obtained.
Melting point 221.0-221.8 [deg.] C.

  As in Example 201, using N-methyl- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) carbamic acid benzyl ester prepared in Example 202. The compound of Example 206 was produced.

Example 206
N-Methyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethylamine trifluoroacetate salt mp 176.2-178.8 ° C.

  The compounds of Example 207 to Example 211 were produced in the same manner as in Example 205, using the corresponding starting materials.

Example 207
(2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) carbamic acid 4-fluorobenzyl ester yield 25%, mp 200.4-202.1 ° C.

Example 208
(2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) carbamic acid ethyl ester yield 26%, mp 182.5-183.4 ° C.

Example 209
(2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) carbamic acid 4-trifluoromethoxybenzyl ester yield 17%, melting point 182.3-184.4 ° C.

Example 210
(6-Nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) carbamic acid 4-chlorobenzyl ester yield 17%, mp 182.6-182.9 ° C.

Example 211
(6-Nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) carbamic acid 4-fluorobenzyl ester yield 17%, mp 164.6-165.1 ° C.

Example 212
Preparation of [3- (2-Chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] -N-methyl-carbamic acid 4-fluorobenzyl ester 2-chloro-4-nitro-1H -Imidazole (0.953 g, 6.46 mmol) and N-methyl- (2-methyl-2-oxiranylmethyl) carbamic acid 4-fluorobenzyl ester (1.964 g, 7.75 mmol) in 20 ml of ethanol Dissolve, add sodium acetate (0.583 g, 7.11 mmol) and heat to reflux overnight. The ethanol was concentrated under reduced pressure, and the residue was extracted with ethyl acetate and water. After drying over sodium sulfate and filtration, the filtrate was concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (n-hexane / ethyl acetate = 1/1) to give [3- (2-chloro-4-nitroimidazol-1-yl) -2 as a colorless oil. -Hydroxy-2-methylpropyl] -N-methyl-carbamic acid 4-fluorobenzyl ester (1.683 g, 65% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.17 (3 H, s), 3.06 (3 H, s), 3. 25 (1 H, d, J = 14.7 Hz), 3.51 (1 H, d, J = 14.7 Hz); 00 (2H, s), 5.12 (2H, s), 6.95 to 7.09 (2H, m), 7.27 to 7.41 (2H, m), 8.07 (1 H, s) .

  The compound of Example 213 was prepared in the same manner as Example 212 using N-methyl- (2-oxiranylmethyl) carbamic acid 4-fluoro-benzyl ester.

Example 213
[3- (2-Chloro-4-nitroimidazol-1-yl) -2-hydroxypropyl] -N-methyl-carbamic acid 4-fluorobenzyl ester yield 51%
¹ H-NMR (CDCl ₃ ) δ ppm:
3.04 (3H, s), 3.27-3.55 (2H, m), 3.73-4.23 (4H, m), 5.11 (2H, s), 7.00-7. 14 (2H, m), 7.27-7.41 (2H, m), 7.96 (1 H, s).

Example 214
Preparation of N-Methyl- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) carbamic Acid 4-Fluorobenzyl Ester Prepared as in Example 212 [3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] -N-methyl-carbamic acid 4-fluorobenzyl ester (1.683 g, 4.20 mmol); -Dissolve in 30 ml of dioxane, add sodium hydride (0.185 g, 4.62 mmol), stir at room temperature for 1 hour and then heat to reflux for 7 hours. The solvent was evaporated under reduced pressure, water was added to the residue, and the precipitate was collected by filtration. It was purified by silica gel column chromatography (n-hexane / acetone = 2/1). The resulting solid is washed with a mixed solvent of n-hexane and ethyl acetate, filtered and dried under reduced pressure to give N-methyl- (2-methyl-6-nitro-2,3-dihydroimidazo) as a colorless solid. [2,1-b] oxazol-2-ylmethyl) carbamic acid 4-fluorobenzyl ester (0.381 g, yield 25%) was obtained.
Mp 168.9-169.9 ° C.

  As in Example 214, using [3- (2-Chloro-4-nitroimidazol-1-yl) -2-hydroxypropyl] -N-methyl-carbamic acid 4-fluorobenzyl ester prepared in Example 213; Thus, the compound of Example 215 is produced.

Example 215
N-methyl- (6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) carbamic acid 4-fluorobenzyl ester yield 16%, mp 124.5-128.1 ° C.

  The compounds of Example 216 to Example 220 were produced in the same manner as in Example 179, using the corresponding starting materials.

Example 216
(S) -1- (2-Chloro-4-nitroimidazol-1-yl) -3-{[1- (4-chlorophenyl) piperidin-4-yl] -N-methyl-amino} -2-hydroxy- 2-Methylpropane yellow oil, yield 98%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.13 (3 H, s), 1.57-1. 82 (4 H, m), 2. 38-2. 71 (4 H, m), 2. 40 (3 H, m), 3. 65-3. 71 (2H, m), 3.82 (1 H, s), 3.89-4.01 (2 H, m), 6.81-6.86 (2 H, m), 7.16-7.22 ( 2H, m), 8.06 (1 H, s).

Example 217
(S) -1- (2-Chloro-4-nitroimidazol-1-yl) -3-{[1- (4-trifluoromethoxyphenyl) piperidin-4-yl] -N-methyl-amino} -2 -Hydroxy-2-methylpropane yellow oil, yield 91%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.13 (3H, s), 1.59-1.83 (4H, m), 2.41 (3H, s), 2.43-2.73 (5H, m), 3.66-3. 73 (2H, m), 3.84 (1 H, s), 3.93 (1 H, d, J = 14.2 Hz), 4.00 (1 H, d, J = 14.2 Hz), 6.86- 6.91 (2H, m), 7.07-7.12 (2H, m), 8.06 (1 H, s).

Example 218
(S) -1- (2-Chloro-4-nitroimidazol-1-yl) -3-{[1- (4-trifluoromethylphenyl) piperidin-4-yl] -N-methyl-amino} -2 -Hydroxy-2-methylpropane yellow oil, yield 96%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.13 (3H, s), 1.54-1.70 (2H, m), 1.77-1.84 (2H, m), 2.40 (3H, s), 2.42-2. 60 (3H, m), 2.72-2.82 (2H, m), 3.79 (1H, s), 3.84-3.89 (2H, m), 3.92 (1 H, d, J = 14.2 Hz), 3.99 (1 H, d, J = 14.2 Hz), 6.91 (2 H, d, J = 8.7 Hz), 7.46 (2 H, d, J = 8.7 Hz ), 8.06 (1 H, s).

Example 219
(S) -1- (2-Chloro-4-nitroimidazol-1-yl) -3-{[1- (4-cyanophenyl) piperidin-4-yl] -N-methyl-amino} -2-hydroxy -2-Methylpropane yellow oil, 89% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
1.13 (3H, s), 1.51-1.65 (2H, m), 1.77-1.84 (2H, m), 2.39 (3H, s), 2.42-2. 62 (3H, m), 2.76-2.88 (2H, m), 3.75 (1 H, s), 3.88-4.03 (4H, m), 6.81-6.88 ( 2H, m), 7.45-7.53 (2H, m), 8.05 (1 H, s).

Example 220
(S) -1- (2-Chloro-4-nitroimidazol-1-yl) -3-{[1- (tert-butoxycarbonyl) piperidin-4-yl] -N-methyl-amino} -2-hydroxy -2- methylpropane yellow oil,
¹ H-NMR (CDCl ₃ ) δ ppm:
1.11 (3H, s), 1.46 (9H, s), 1.50-1.80 (4H, m), 2.37 (3H, s), 2.40-2.75 (5H, m), 3.90 (1 H, d, J = 14.2 Hz), 3.99 (1 H, d, J = 14.2 Hz), 4.22 (2 H, br), 8.05 (1 H, s) .

  The compounds of Examples 221 to 225 were produced from the compounds produced in Examples 216 to 220 in the same manner as in Example 188.

Example 221
(S) -2-{[1- (4-chlorophenyl) piperidin-4-yl] -N-methyl-aminomethyl} -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b ] Oxazole white powder, 47% yield
MS 406 (M + 1) ⁺
Mp 179.2-182.1 ° C.

Example 222
(S) -2-{[1- (4-trifluoromethoxyphenyl) piperidin-4-yl] -N-methyl-aminomethyl} -2-methyl-6-nitro-2,3-dihydroimidazo [2,2, 1-b] oxazole mp 127.2-129.7 ° C.

Example 223
(S) -2-{[1- (4-trifluoromethylphenyl) piperidin-4-yl] -N-methyl-aminomethyl} -2-methyl-6-nitro-2,3-dihydroimidazo [2,2, 1-b] oxazole melting point 131.5-133.6 ° C.

Example 224
(S) -2-{[1- (4-cyanophenyl) piperidin-4-yl] -N-methyl-aminomethyl} -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-] b] Oxazole melting point 149-152 [deg.] C.

Example 225
(S) -2-{[1- (tert-butoxycarbonyl) piperidin-4-yl] -N-methyl-aminomethyl} -2-methyl-6-nitro-2,3-dihydroimidazo [2,1- b] Oxazole pale yellow powder crystal, yield 37%
Melting point 138.5-140.3 ° C.

Example 226
(S) -2-{[1- (4-trifluoromethylbenzyloxycarbonyl) piperidin-4-yl] -N-methyl-aminomethyl} -2-methyl-6-nitro-2,3-dihydroimidazo [ Preparation of 2,1-b] oxazole (S) -2-{[1- (tert-butoxycarbonyl) piperidin-4-yl] -N-methyl-aminomethyl} -2-methyl- prepared in Example 225 6-Nitro-2,3-dihydroimidazo [2,1-b] oxazole (400 mg, 1.01 mmol) was dissolved in 1 ml of methylene chloride, to which 1 ml of trifluoroacetic acid was added and stirred at room temperature for 5 hours. The reaction solution was concentrated under reduced pressure, and 1 ml each of methylene chloride and triethylamine were added. The mixture was stirred at room temperature for 5 minutes, concentrated under reduced pressure, and the residue was dissolved in 8 ml of DMF. Thereto is added a mixture of 4- (trifluoromethyl) benzyl alcohol (267 mg, 1.51 mmol) and 1,1'-carbonyldiimidazole (246 mg, 1.51 mmol) dissolved in 2 ml of DMF and stirred for 4 hours at room temperature. Stir at room temperature overnight. The reaction mixture was poured into water, extracted with ethyl acetate, and the organic phase was washed with saturated brine. After drying over magnesium sulfate, it was filtered. The resulting filtrate was concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (methylene chloride / methanol = 200/1). Crystallization is carried out from methylene chloride-isopropyl ether, followed by filtration and drying under reduced pressure to obtain a slightly yellow powder of (S) -2-{[1- (4-trifluoromethylbenzyloxycarbonyl) piperidin-4-yl]. -N-Methyl-aminomethyl} -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole (341 mg, yield 68%) was obtained.
Melting point 110.6-113.1 ° C.

  The compounds of Example 227 and Example 228 were produced in the same manner as in Example 226, using the corresponding starting materials.

Example 227
(S) -2-{[1- (4-trifluoromethoxybenzyloxycarbonyl) piperidin-4-yl] -N-methyl-aminomethyl} -2-methyl-6-nitro-2,3-dihydroimidazo [ 2,1-b] oxazole melting point 84.2-86.8 ° C.

Example 228
(S) -2-{[1- (4-chlorobenzyloxycarbonyl) piperidin-4-yl] -N-methyl-aminomethyl} -2-methyl-6-nitro-2,3-dihydroimidazo [2,2, 1-b] oxazole melting point 116.2-16.6.degree.

Example 229
Preparation of 2-Methyl-6-nitro-2- [4- (4-trifluoromethylbenzyloxy) piperidin-1-ylmethyl] -2,3-dihydroimidazo [2,1-b] oxazole Prepared in Example 6 2-chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitroimidazole (122 mg, 0.56 mmol) and 4- [4- (trifluoromethyl) benzyloxy] piperidine (188 mg, 4.86 mol) were dissolved in 10 ml DMF and stirred at 70-75 ° C. for 5 hours. The reaction solution was returned to room temperature, poured into water, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride / methanol = 50/1) to give a yellow oil.

The yellow oily substance was dissolved in 10 ml of DMF, sodium hydride (134 mg, 3.36 mmol) was added under ice-cooling, and the mixture was warmed to room temperature and stirred for 1 hour. The reaction solution was poured into water and extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 10/1) and crystallized from ethyl acetate-diisopropyl ether to give 2-methyl-6-white powder as a white powder. Nitro-2- [4- (4-trifluoromethylbenzyloxy) piperidin-1-ylmethyl] -2,3-dihydroimidazo [2,1-b] oxazole (41 mg, 17% yield) was obtained.
MS 440 (M-1) ^+
1 H-NMR (CDCl ₃ ) δ ppm:
1.41 to 1.70 (2H, m), 1.60 (3H, s), 1.75 to 1.88 (2H, m), 2.26 to 2.40 (1 H, m), 45-2.55 (2H, m), 2.72-2.95 (3H, m), 3.38 (1H, m), 3.89 (1 H, d, J = 9.6 Hz), 4. 31 (1 H, d, J = 9.6 Hz), 4.54 (2 H, s), 7.43 (2 H, d, J = 8.2 Hz), 7.53 (1 H, s), 7.79 ( 2H, d, J = 8.2 Hz).

Example 230
Preparation of 1- (2-Chloro-4-nitroimidazol-1-yl) -2-methyl-3- [4- (4-trifluoromethylphenoxy) piperidin-1-yl] propan-2-ol Example 5 2-chloro-1- [2-hydroxy-2-methyl-3- (4-methylbenzenesulfonyloxy) propyl] -4-nitroimidazole (0.30 g, 0.77 mmol) and 4- (4 Sodium iodide (0.13 g, 0.77 mmol) and triethylamine (0.12 ml, 0.77 mmol) in a solution of trifluoromethylphenoxy) piperidine (0.21 g, 0.85 mmol) in DMF (6 ml) In addition, it was stirred at 80 ° C. for 7 hours. Water was added to the reaction solution, extracted with ethyl acetate, washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 9/1) to give 1- (2-chloro-4-nitroimidazol-1-yl) -2-methyl-3- [4 as a yellow oil. -(4-Trifluoromethylphenoxy) piperidin-1-yl] propan-2-ol (0.23 g, yield 63%) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.14 (3H, s), 1.76-2.04 (4H, m), 2.36 (1H, d, J = 14.0 Hz), 2.43-2.72 (3H, m), 2.76 to 3.00 (2H, m), 3.46 to 3.52 (1H, br), 3.98 (2H, s), 4.37 to 4. 50 (1 H, m), 6. 91-7.00 (2H, m), 7.48-7. 61 (2H, m), 8.05 (1 H, s).

  The compound of Example 231 was produced in the same manner as in Example 230, using the corresponding starting materials.

Example 231
1- (2-chloro-4-nitroimidazol-1-yl) -2-methyl-3- [4- (4-trifluoromethoxyphenoxy) piperidin-1-yl] propan-2-ol yield 61%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.14 (3 H, s), 1.74-2.04 (4 H, m), 2. 35 (1 H, d, J = 13.9 Hz), 2.40 (1 H, d, J = 13.9 Hz) ), 2.42 to 2.70 (2H, m), 2.74 to 3.00 (2H, m), 3.98 (2H, s), 4.25 to 4.41 (1 H, m), 6.86-6.92 (2 H, m), 7.1 1-7. 15 (2 H, m), 8.05 (1 H, s).

Example 232
Preparation of 1- (2-Chloro-4-nitroimidazol-1-yl) -2-methyl-3- [4- (4-trifluoromethoxyphenylamino) piperidin-1-yl] propan-2-ol Example 2-Chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitroimidazole (0.3 g, 1.38 mmol) prepared in 6 and piperidin-4-yl- (4-trifluoromethoxy A solution of phenyl) amine (0.43 g, 1.66 mmol) in DMF (8 ml) was stirred at 80 ° C. for 2 hours. To the reaction solution was added water, extracted with ethyl acetate, dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (n-hexane / ethyl acetate = 1/1) to give 1- (2-chloro-4-nitroimidazol-1-yl) -2-methyl-3- [yellow oil] 4- (4-Trifluoromethoxyphenylamino) piperidin-1-yl] propan-2-ol (0.37 g, 56% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.13 (3H, s), 1.39-1.63 (2H, m), 1.96-2.09 (2H, m), 2.47 (1 H, d, J = 13.9 Hz), 2.43-2.63 (3H, m), 2.67-2.83 (1H, m), 2.87-3.02 (1H, m), 3.15-3. 39 (1H, m) ), 3.41-3.72 (2H, m), 3.97 (2H, s), 6.46-6.59 (2H, m), 6.96-7.09 (2H, m), 8.05 (1 H, s).

Example 233
Preparation of 2-Methyl-6-nitro-2- [4- (4-trifluoromethylphenoxy) piperidin-1-ylmethyl] -2,3-dihydroimidazo [2,1-b] oxazole Prepared as in Example 230 1- (2-Chloro-4-nitroimidazol-1-yl) -2-methyl-3- [4- (4-trifluoromethylphenoxy) piperidin-1-yl] propan-2-ol (225 mg, 0. 1; Sodium hydride (23 mg, 0.59 mmol) was added to a solution of 49 mmol) in DMF (2.5 ml) with ice cooling and stirred at 0 ° C. for 1 hour. Ice water and ethyl acetate are added thereto, and the precipitate is collected by filtration, washed with water, recrystallized from methylene chloride and diisopropyl ether, washed with n-hexane, and slightly yellow solid 2-methyl-6-nitro- 2- [4- (4-Trifluoromethylphenoxy) piperidin-1-ylmethyl] -2,3-dihydroimidazo [2,1-b] oxazole (80 mg, 39% yield) was obtained.
113-114 ° C.

  The compound of Example 234 was produced in the same manner as in Example 233, using the corresponding starting materials.

Example 234
2-Methyl-6-nitro-2- [4- (4-trifluoromethoxyphenoxy) piperidin-1-ylmethyl] -2,3-dihydroimidazo [2,1-b] oxazole mp 117-119 ° C.

Example 235
Preparation of 2- [4- (4-Trifluoromethoxyphenyl) aminopiperidin-1-yl] methyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole Example 33 1- (2-Chloro-4-nitroimidazol-1-yl) -2-methyl-3- [4- (4-trifluoromethoxyphenylamino) piperidin-1-yl] propan-2-ol (369 mg) prepared , 0.77 mmol), and in the same manner as in Example 232, 2- [4- (4-trifluoromethoxyphenylamino) piperidin-1-yl] methyl-2-methyl-6-nitro- yellow powder 2,3-Dihydroimidazo [2,1-b] oxazole (25 mg, 7% yield) was obtained.
MS 441 (M ⁺ )
¹ H-NMR (CDCl ₃ ) δ ppm:
1.11-1.40 (2H, m), 1.61 (3H, s), 1.85-2.01 (2H, m), 2.37 (1 H, dt, J = 2.7 Hz, 11 .4 Hz), 2.46-2.59 (2 H, m), 2.76-2.84 (1 H, m), 2.87 (1 H, d, J = 14.9 Hz), 2.95-3 .03 (1 H, m), 3.10-3.25 (1 H, m), 3.50 (1 H, d, J = 7.8 Hz), 3.90 (1 H, d, J = 9.7 Hz) , 4.29 (1 H, d, J = 9.7 Hz), 6.46-6.52 (2 H, m), 6.98-7. 01 (2 H, m), 7. 50 (1 H, s) .

Example 236
Preparation of N-Methyl- [1- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperidin-4-yl] carbamic acid tert-butyl ester 2 -Chloro-4-nitro-1H-imidazole (1.08 g, 7.31 mmol), N-methyl- [1- (2-methyl-2-oxiranylmethyl) piperidin-4-yl] carbamic acid tert- The butyl ester (2.08 g, 7.31 mmol) and sodium acetate (660 mg, 8.04 mmol) were heated to reflux overnight in 15 ml of 1-propanol. The reaction solution was concentrated under reduced pressure, extracted with methylene chloride, dried over sodium sulfate and filtered. The obtained filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (methylene chloride / methanol = 200/1), crystallized with methylene chloride-isopropyl ether, filtered and dried under reduced pressure. Thus, N-methyl- [1- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperidin-4-yl] carbamic acid tert of white powder is obtained. -Butyl ester (348 mg, 12% yield) was obtained.
MS 396 (M + 1) ⁺
Mp 198.8-201.1 ° C.

Example 237
Preparation of N-Methyl- [1- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperidin-4-yl] carbamic acid benzyl ester Example 236 -Methyl- {1- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperidin-4-yl} carbamic acid tert-butyl ester prepared in (207 mg, 0.52 mmol) was dissolved in 5 ml of methylene chloride, 5 ml of trifluoroacetic acid was added and stirred for 5 hours at room temperature. The reaction solution was concentrated under reduced pressure, and 5 ml of methylene chloride, 1 ml of triethylamine and benzyl chlorocarbonate (0.15 ml, 1.05 mmol) were added to the residue and stirred at room temperature for 30 minutes. The reaction solution was poured into water, extracted with methylene chloride, dried over sodium sulfate and filtered. The obtained filtrate was concentrated under reduced pressure, and the residue was separated and purified by silica gel column chromatography (methylene chloride / methanol = 200/1). Crystallization is performed from ethyl acetate-isopropyl ether, followed by filtration and drying under reduced pressure to obtain N-methyl- [1- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-] as a white powder. b] Oxazol-2-ylmethyl) piperidin-4-yl] carbamic acid benzyl ester (184 mg, 82% yield) was obtained.
MS 430 (M + H) ⁺
Melting point 138.7-139.2 ° C.

  The compound of Example 238 was prepared in the same manner as Example 237 using 4-chlorobenzyl chlorocarbonate. In addition, the compound of Example 239 was produced in the same manner as Example 237 using 4-chlorophenyl acetyl chloride.

Example 238
N-Methyl- [1- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperidin-4-yl] carbamic acid 4-chlorobenzyl ester melting point 147 2-149.2 ° C.

Example 239
2- {4- [N- (4-Chlorophenylacetyl) -N-methyl] aminopiperidin-1-yl} methyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole melting point 206.8-208 ° C.

Example 240
2-Methyl-2- {4- [N-methyl-N- (4-trifluoromethoxyphenyl)] aminopiperidin-1-yl} methyl-6-nitro-2,3-dihydroimidazo [2,1-b Preparation of Oxazol] 2- [4- (4-Trifluoromethoxyphenyl) aminopiperidin-1-yl] methyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1 prepared in Example 235] -B] To a solution of 60 mg (0.14 mmol) in methanol (2 ml) was added 37% formaldehyde solution (51 μl, 0.70 mmol) and sodium cyanoborohydride (26 mg, 0.42 mmol), and further added Stir at room temperature for 30 minutes. The reaction solution was ice-cooled, acetic acid (23 μl, 0.42 mmol) was added, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was further ice-cooled, aqueous sodium hydrogen carbonate solution was added, extraction was performed with methylene chloride, drying with magnesium sulfate, and concentration under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 1/1), crystallized with diisopropyl ether, 2-methyl-2- {4- [N-methyl-N- (4) as slightly yellow solid -Trifluoromethoxyphenyl)] aminopiperidin-1-yl} methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole (40 mg, yield 65%) was obtained.
Mp 135-136 ° C.

Example 241
Preparation of 2- [4- (4-chlorobenzyl) oxypiperidin-1-yl] methyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole 2-chloro-4- Nitro-1H-imidazole (1.5 g, 10.17 mmol), 4- (4-chlorobenzyloxy) -1- (2-methyl-2-oxiranylmethyl) piperidine (2.5 g, 8.45 mmol A mixture of sodium bicarbonate (0.86 g, 10.24 mmol) and ethanol (15 ml) was heated to reflux for 15 hours. The reaction solution was returned to room temperature and concentrated under reduced pressure. To the residue was added water, extracted with methylene chloride, dried over sodium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 10/1) to give 2- [4- (4-chlorobenzyl) oxypiperidin-1-yl] methyl-2-methyl-6-white powder. Nitro-2,3-dihydroimidazo [2,1-b] oxazole (662 mg, 16% yield) was obtained.
Melting point 129-130 [deg.] C.

Example 242
2- {4- [N- (4-Chlorophenyl) -N-methyl] aminopiperidin-1-yl} methyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole Preparation 2-Chloro-1- (2-methyloxiranylmethyl) -4-nitroimidazole (350 mg, 1.61 mmol) prepared in Example 6; 4- [N- (4-chlorophenyl) -N-methyl A mixture of amino] piperidine (373 mg, 1.66 mmol) and DMF (15 ml) was stirred at 70 ° C. for 5 hours. To this reaction solution was added 77 mg (1.93 mmol) of sodium hydride under ice-cooling, and the mixture was stirred at the same temperature for 1 hour. The reaction solution was poured into ice water and extracted twice with ethyl acetate. The organic phases were combined, washed three times with water, then washed with saturated brine, dried over sodium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 1/1) to obtain 2- {4- [N- (4-chlorophenyl) -N-methyl] aminopiperidin-1-yl as pale yellow powdery crystals. } Methyl 2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole (307 mg, 47% yield) was obtained.
Melting point 186-187.8 [deg.] C.

  Analog of Example 242 with 4- (4-trifluoromethoxybenzyl) piperidine, 4- (4-trifluoromethylbenzyl) piperidine, 4- (4-chlorobenzyl) piperidine or 4- (chlorobenzoyl) piperidine The compounds of Example 243 to Example 246 were prepared.

Example 243
2-Methyl-6-nitro-2- [4- (4-trifluoromethoxybenzyl) piperidin-1-yl] methyl-2,3-dihydroimidazo [2,1-b] oxazole melting point 143.5-145 ° C .

Example 244
2-Methyl-6-nitro-2- [4- (4-trifluoromethylbenzyl) piperidin-1-yl] methyl-2,3-dihydroimidazo [2,1-b] oxazole mp 125-126 ° C.

Example 245
2- [4- (4-Chlorobenzyl) piperidin-1-yl] methyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole melting point 109-110.5 ° C
Example 246
2- [4- (4-Chlorobenzoyl) piperidin-1-yl] methyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole mp 165-167 ° C.

Example 247
Preparation of 2-Methyl-6-nitro-2- [4- (4-trifluoromethylbenzoyl) piperidin-1-yl] methyl-2,3-dihydroimidazo [2,1-b] oxazole Prepared in Example 6 2-chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitroimidazole (80 mg, 0.37 mmol), 4- (4-trifluoromethylbenzoyl) piperidine (95 mg, 0.37) A mixture of mmol), sodium acetate (150 mg, 1.83 mmol) and DMF (2 ml) was stirred at 80 ° C. overnight. The reaction was poured into water and extracted twice with ethyl acetate. The organic phases were combined, washed three times with water, then washed with saturated brine, dried over sodium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (ethyl acetate / n-hexane = 1/1) to give white powder of 2-methyl-6-nitro-2- [4- (4-trifluoromethylbenzoyl) piperidine-1-]. [Ill] methyl-2,3-dihydroimidazo [2,1-b] oxazole (46 mg, 29% yield) was obtained.
Melting point 172-174 [deg.] C.

  The compound of Example 248 was produced in the same manner as in Example 247 using the corresponding starting materials.

Example 248
2-Methyl-6-nitro-2- [4- (4-trifluoromethoxybenzoyl) piperidin-1-yl] -2,3-dihydroimidazo [2,1-b] oxazole mp 165-167 ° C.

Example 249
Preparation of (S) -2- [4- (3,4-Dichlorobenzyloxy) piperidin-1-ylmethyl] -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole (R) -2-Chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitroimidazole (396 mg, 1.82 mmol) prepared in Example 12 and 4- (3,4-dichlorobenzyl) Oxy) piperidine (614 mg, 2.36 mol) was stirred in 15 ml DMF at 70-75 ° C. for 4 hours. The reaction solution was allowed to cool to room temperature, poured into water, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride / methanol = 50/1) to give a yellow oil.

The yellow oil was dissolved in 15 ml of DMF, 87 mg (2.18 mmol) of sodium hydride was added under ice-cooling, and the mixture was stirred overnight at room temperature. The reaction solution was poured into water and extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 10/1), and crystallization is performed from methylene chloride-diisopropyl ether to give (S) -2- [4- (3,4-dichloro) as a white powder. Benzyloxy) piperidin-1-ylmethyl] -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole (431 mg, yield 44%) was obtained.
MS 441 (M ⁺ )
Melting point 132.0-136.0 ° C.

Example 250
(S)-[1- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperidin-4-yl]-(4-trifluoromethoxyphenyl) Preparation of Methanone (R) -2-Chloro-1- (2-methyloxiranylmethyl) -4-nitroimidazole (1.0 g, 4.6 mmol) prepared in Example 12 and 4- (4-Tri) From (Fluoromethoxybenzoyl) piperidine (1.3 g, 4.8 mmol), according to a similar method to Example 249, (S)-[1- (2-Methyl-6-nitro-2,3-) as a slightly yellow powder Dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperidin-4-yl]-(4-trifluoromethoxyphenyl) methanone (771 mg, yield 37%) was obtained.
113.0-115.0 ° C.

Example 251
Preparation of (S) -1- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperidine-4-carboxylic acid ethyl ester 2-chloro-4- Nitro-1H-imidazole (3.7 g, 25.1 mmol), (S) -1- (2-methyl-2-oxiranylmethyl) piperidine-4-carboxylic acid ethyl ester (4.8 g, 21.1 Mmole) and sodium bicarbonate (2.2 g, 25.1 mmol) were heated to reflux overnight in 25 ml of ethanol. The reaction mixture was concentrated under reduced pressure, water was added to the residue, and the mixture was extracted with methylene chloride. The organic phase was washed with brine, dried over magnesium sulfate and filtered. The obtained filtrate is concentrated under reduced pressure, and the residue is separated and purified by silica gel column chromatography (n-hexane / ethyl acetate = 3/1), and crystallized with diethyl ether to obtain a white powder (S) -1- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperidine-4-carboxylic acid ethyl ester (1.4 g, 20% yield) Obtained.
Mp 101.0-103.0 ° C.

Example 252
(S) -2-Methyl-6-nitro-2- [4- (4-trifluoromethoxyphenyl) -1,2,3,6-tetrahydropyridin-1-ylmethyl] -2,3-dihydroimidazo [2 Preparation of 1,1-b] oxazole 4- (4-Trifluoromethoxyphenyl) -1,2,3,6-tetrahydro-2H-pyridine (0.985 g, 4.05 mmol) and prepared in Example 12 ( R) 2-Chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitroimidazole (0.839 g, 3.86 mmol) was added to 15 ml DMF and stirred at 60 ° C. for 8 hours. After extraction with ethyl acetate, the organic phases were combined and washed with water and brine. After drying over sodium sulfate, it was filtered. The resulting filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane / ethyl acetate = 4/1). The resulting oil was dissolved in 20 ml DMF and cooled to 4 ° C. To this solution was added sodium hydride (94 mg, 2.35 mmol) and stirred overnight at room temperature. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic phases were combined, washed with water and saturated brine, dried over sodium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (n-hexane / ethyl acetate = 1/1) and then dried under reduced pressure to obtain a slightly yellow solid of (S) -2-methyl-6-nitro-2- [4- (4-) 4-trifluoromethoxyphenyl) -1,2,3,6-tetrahydropyridin-1-ylmethyl] -2,3-dihydroimidazo [2,1-b] oxazole (0.192 g, 23% yield) is obtained The
¹ H-NMR (CDCl ₃ ) δ ppm:
1.68 (3H, s), 2.46-3.39 (8H, m), 3.95 (1 H, d, J = 10.2 Hz), 4.49 (1 H, br), 5.98 ( 1 H, s), 7.16 (2 H, d, J = 8.3 Hz), 7. 35 (2 H, d, J = 8.3 Hz), 7.53 (1 H, s).

Example 253
(S) -1- (2-Chloro-4-nitroimidazol-1-yl) -2-methyl-3- [4- (4-trifluoromethylphenoxy) piperidin-1-yl] propan-2-ol Preparation (R) -2-Chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitroimidazole (500 mg, 2,30 mmol) prepared in Example 12 and 4- (4-trifluoro) Methylphenoxy) piperidine (730 mg, 3.0 mmol) was stirred in 10 ml DMF at 70-75 ° C. for 5 hours. The reaction solution was returned to room temperature, poured into water and extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (methylene chloride / methanol = 50/1) to give (S) -1- (2-chloro-4-nitroimidazole-1 as a yellow oily substance. -Yl) -2-methyl-3- [4- (4-trifluoromethylphenoxy) piperidin-1-yl] propan-2-ol (1.06 g, yield 99%) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.14 (3 H, s), 1.80-2.04 (4 H, m), 2, 38 (1 H, d, J = 14.0 Hz), 2.48-2.68 (2 H, m), 2.52 (1 H, d, J = 14.0 Hz), 2.77-2.95 (2 H, m), 3.73 (1 H, s), 4.01 (2 H, s), 4.39- 4.46 (1 H, m), 6.93-6.97 (2 H, m), 7.49-7.55 (2 H, m), 8.08 (1 H, s).

Example 254
(S) -1- (2-Chloro-4-nitroimidazol-1-yl) -2-methyl-3- [4- (4-trifluoromethylbenzyloxy) piperidin-1-yl] propan-2-ol Preparation of (R) -2-Chloro-1- (2-methyloxiranylmethyl) -4-nitroimidazole (700 mg, 3.22 mmol) prepared in Example 12 and 4- (4-trifluoromethylbenzyl) Oxy) piperidine (1.09 g, 4.86 mol) was stirred in 10 ml DMF at 70-75 ° C. for 4 hours. The reaction solution was returned to room temperature, poured into water and extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (methylene chloride / methanol = 50/1) to give (S) -1- (2-chloro-4-nitroimidazole-1 as a yellow oil. -Yl) -2-methyl-3- [4- (4-trifluoromethylbenzyloxy) piperidin-1-yl] propan-2-ol (1.36 g, yield 87%) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.12 (3 H, s), 1.61-1. 78 (2 H, m), 1. 88-1. 96 (2 H, m), 2. 32 (1 H, d, J = 13.9 Hz), 2.35-2.56 (2H, m), 2.47 (1H, d, J = 13.9 Hz), 2.72-2.81 (1H, m), 2.86-2.95 (1H , M), 3.44-3.51 (1 H, m), 3.63 (1 H, bs), 3.97 (2 H, s), 4.59 (2 H, s), 7.43-7. 47 (2H, m), 7.58-7. 62 (2H, m), 8.05 (1 H, s).

  The compounds of Examples 255 to 260 shown in the following Table were produced in the same manner as in Example 254, using the corresponding starting materials.

Example 261
(S) -1- (2-Chloro-4-nitroimidazol-1-yl) -2-methyl-3- [4- (3-phenyl-2-propenyloxy) piperidin-1-yl] propane-2- Preparation of the (R) -2-chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitroimidazole (0.198 g, 0.910 mmol) prepared in Example 12 and 4- (4) Using 3-phenyl-2-propenyloxy) piperidine (0.198 g, 0.910 mmol) and according to a method similar to Example 254, (S) -1- (2-chloro-4-nitro) as a brown oil Imidazol-1-yl) -2-methyl-3- [4- (3-phenyl-2-propenyloxy) piperidin-1-yl] propan-2-ol (0.192 g, yield 49%) was obtained. .
¹ H-NMR (CDCl ₃ ) δ ppm:
1.12 (3 H, s), 1.55-1.98 (4 H, m), 2.28-2.94 (6 H, m), 3.41-3. 49 (1 H, m), 3. 62 (1H, br), 3.95 (2H, s), 4.16 (1H, d, J = 6.0 Hz), 4.17 (1 H, d, J = 6.0 Hz), 6.28 ( 1 H, ddd, J = 6.0 Hz, 6.0 Hz, 15.9 Hz), 6.60 (1 H, d, J = 15.9 Hz), 7.21 to 7.42 (5 H, m), 8.05 (1 H, s).

Example 262
(S) -1- (2-chloro-4-nitroimidazol-1-yl) -3- {4- [3- (4-chlorophenyl) -2-propenyloxy] piperidin-1-yl} -2-methyl Preparation of propan-2-ol (R) -2-Chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitroimidazole prepared in Example 12 (0.217 g, 1.00 mmol) And 4- [3- (4-chloro-phenyl) allyloxy] piperidine (0.250 g, 0.995 mmol) in the same manner as in Example 254 give (S) -1- (2-) as a brown liquid. Chloro-4-nitroimidazol-1-yl) -3- {4- [3- (4-chlorophenyl) -2-propenyloxy] piperidin-1-yl} -2-methylpropan-2-ol (0.263 g , Yield 56%).
¹ H-NMR (CDCl ₃ ) δ ppm:
1.12 (3 H, s), 1.55-2.01 (4 H, m), 2.28-2.99 (6 H, m), 3. 40-3.51 (1 H, m), 3. 60 (1H, br), 3.96 (2H, s), 4.14-4.16 (2H, m), 6.20-6.31 (1 H, m), 6.56 (1 H, d, J = 15.7 Hz), 7.19-7.34 (4 H, m), 8.05 (1 H, s).

Example 263
Preparation of (S) -2- {4- [3- (4-chlorophenyl) propoxy] piperidin-1-ylmethyl} -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole (R) -2-Chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitroimidazole (0.103 g, 0.473 mmol) prepared in Example 12 and 4- [3- (3-chloro) 4-Chlorophenyl) propoxy] piperidine (0.109 g, 0.430 mmol) was dissolved in 2 ml DMF and stirred at 60 ° C. for 4 hours. After extraction with ethyl acetate, the organic phases were combined and washed with water and brine. After drying over sodium sulfate, it was filtered. The resulting filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane / ethyl acetate = 2/3). The resulting oil was dissolved in 2 ml DMF and cooled to 4 ° C. To this solution was added sodium hydride (15 mg, 0.375 mmol) and stirred at room temperature for 3 hours. Water was added to the reaction solution, and the precipitate was collected by filtration. The precipitate is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 6/1) and recrystallized from ethyl acetate / n-hexane = 1/3 (6 ml) to give white powder crystals of (S) -2- {4- [3- (4-Chlorophenyl) propoxy] piperidin-1-ylmethyl} -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole (36 mg, 19% yield) I got
Melting point 88.8-91.9 ° C.

Example 264
(S) -1- (2-Chloro-4-nitroimidazol-1-yl) -3- {4- [2- (4-chlorophenyl) ethoxy] piperidin-1-yl} -2-methyl-propane-2 (R) -2-Chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitroimidazole (0.076 g, 0.350 mmol) prepared in Example 12 and 4- By a method similar to Example 254 using [2- (4-chlorophenyl) ethoxy] piperidine (0.080 g, 0.334 mmol), (S) -1- (2-chloro-4) as a slightly yellow oil -Nitroimidazol-1-yl) -3- {4- [2- (4-chlorophenyl) ethoxy] piperidin-1-yl} -2-methyl-propan-2-ol (0.109 g, 71% yield) I got
¹ H-NMR (CDCl ₃ ) δ ppm:
1.10 (3 H, s), 1.51-1. 72 (2 H, m), 1.78-1.92 (2 H, m), 2.24-2.50 (4 H, m), 55-2.88 (4H, m), 3.29-3.39 (1H, m), 3.58-3.66 (3H, m), 3.94 (2H, s), 7.15 ( 2H, d, J = 8.5 Hz), 7.24 (2 H, d, J = 8.5 Hz), 8.04 (1 H, s).

Example 265
(S) -1- (2-Chloro-4-nitroimidazol-1-yl) -2-methyl-3- {4- [2- (4-trifluoromethylphenyl) ethoxy] piperidin-1-yl} propane Preparation of -2-ol Triphenyl- (4-trifluoromethylbenzyl) phosphonium bromide (3.00 g, 5.98 mmol) was dissolved in 50 ml of DMSO and sodium hydride (0.239 g, 98 mmol) was added and stirred at room temperature for 1 hour. Thereto, 10 ml of a solution of 4-formyloxypiperidine-1-carboxylic acid benzyl ester (1.497 g, 5.69 mmol) in DMSO was added dropwise and stirred at 60 ° C. for 7 hours. After extraction with ethyl acetate twice, the organic phases were combined, washed with water and saturated brine, dried over sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane / ethyl acetate = 4/1). The residue was further purified by silica gel column chromatography (methylene chloride / ethyl acetate = 9/1) to obtain 4- [2- (4-trifluoromethylphenyl) vinyloxy] piperidine-1-carboxylic acid benzyl ester as a colorless oil. .

  The obtained 4- [2- (4-trifluoromethylphenyl) vinyloxy] piperidine-1-carboxylic acid benzyl ester is dissolved in 10 ml of ethanol, and 90 mg of 10% Pd / C is used as a catalyst at normal pressure under room temperature. The catalytic reduction was performed. The reaction solution was filtered through celite, and the filtrate was concentrated under reduced pressure to obtain 4- [2- (trifluoromethylphenyl) ethoxy] piperidine as a brown liquid.

The obtained 4- [2- (trifluoromethylphenyl) ethoxy] piperidine and (R) -2-chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitro prepared in Example 12 A brown oil of (S) -1- (2-chloro-4-nitroimidazol-1-yl) -2-methyl- was obtained in the same manner as in Example 254 using 0.184 g (0.844 mmol) of imidazole. 3- {4- [2- (4-Trifluoromethylphenyl) ethoxy] piperidin-1-yl} propan-2-ol (0.088 g, 3% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.10 (3 H, s), 1.49-1.92 (4 H, m), 2.24-2. 81 (6 H, m), 2. 92 (2 H, t, J = 6.8 Hz), 3.30-3.35 (1H, m), 3.65 (2H, t, J = 6.8 Hz), 3.94 (2H, s), 7.34 (2 H, d, J = 8.2 Hz ), 7.54 (2 H, d, J = 8.2 Hz), 8.04 (1 H, s).

Example 266
(S) -1- (2-Chloro-4-nitroimidazol-1-yl) -2-methyl-3- [4- (4-trifluoromethoxyphenylamino) piperidin-1-yl] propan-2-ol Preparation of (R) -2-Chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitroimidazole and N-piperidin-4-yl-4-trifluoromethoxyphenyl prepared in Example 12 Similarly to Example 254 using aniline, (S) -1- (2-chloro-4-nitroimidazol-1-yl) -2-methyl-3- [4- (4-tri- (4-trichloro)] as a yellow oil Fluoromethoxyphenylamino) piperidin-1-yl] propan-2-ol (1.36 g, 88% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.13 (3 H, s), 1.41-1. 57 (2 H, m), 2.03-2.08 (2 H, m), 2. 34 (1 H, d, J = 13.9 Hz), 2.49-2.59 (3 H, m), 2.65-2.77 (2 H, m), 3.08-2.16 (2 H, m), 3.24-3. 41 (1 H, m) ), 3.97 (2H, s), 6.47-6.55 (2H, m), 6.98-7.04 (2H, m), 8.05 (1 H, s).

  The compounds of Examples 267 to 269 shown in the following table were prepared in the same manner as in Example 266 using the corresponding starting materials.

Example 270
Preparation of (S) -1- (4-Piperidinopiperidin-1-yl) -3- (2-chloro-4-nitroimidazol-1-yl) -2-methyl-propan-2-ol Example 12 And (R) -2-chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitroimidazole (0.500 g, 2.29 mmol) and 4-piperidinopiperidine (0.. 425 g (2.53 mmol) was dissolved in 5 ml DMF and stirred at 70 ° C. for 5 hours. After extraction with ethyl acetate twice, the organic phases were combined, washed with water and saturated brine, dried over sodium sulfate and filtered. The obtained filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (n-hexane / ethyl acetate = 3/2) using basic silica gel to obtain (S) -1- (brown oil) (4-Piperidinopiperidin-1-yl) -3- (2-chloro-4-nitroimidazol-1-yl) -2-methyl-propan-2-ol (0.656 g, yield 74%) Obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.11 (3 H, s), 1.38-1.89 (10 H, m), 2.18-2.55 (9 H, m), 2. 70-2. 81 (1 H, m), 89-3.01 (1 H, m), 3.67 (1 H, br), 3.94 (1 H, s), 8.05 (1 H, s).

Example 271
(S) -1- (2-Chloro-4-nitroimidazol-1-yl) -2-methyl-3-{[4- (4-trifluoromethoxyphenyl) sulfanyl] piperidin-1-yl} propane-2 (R) -2-Chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitroimidazole prepared in Example 12 and 4- [4- (trifluoromethoxy) phenylsulfanyl Similarly to Example 270, using piperidine, (S) -1- (2-chloro-4-nitroimidazol-1-yl) -2-methyl-3-{[4- (4) as a yellow oil -Trifluoromethoxyphenyl) sulfanyl] piperidin-1-yl} propan-2-ol (3.4 g, yield 99%) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.11 (3H, s), 1.58 to 1.73 (2H, m), 1. 9 to 1.99 (2H, m), 2. 32 (1 H, d, J = 13.9 Hz), 2.41-2.50 (2H, m), 2.46 (1H, d, J = 13.9 Hz), 2.75-3.09 (4H, m), 3.97 (2H, s), 7.11-7.17 (2H, m), 7.36-7.53 (2H, m), 8.04 (1H, s).

Example 272
(S) -1- (2-Chloro-4-nitroimidazol-1-yl) -2-methyl-3- [4- (4-trifluoromethoxybenzyl) piperidin-1-yl] propan-2-ol Preparation, using 4- (4-trifluoromethoxybenzyl) piperidine and (R) -2-chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitroimidazole prepared in Example 12. Analogously to Example 270, (S) -1- (2-chloro-4-nitroimidazol-1-yl) -2-methyl-3- [4- (4-trifluoromethoxybenzyl) piperidine as a yellow oil -1-yl] propan-2-ol crude was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.10 (3 H, m), 1.22 to 1.71 (5 H, m), 2.26 to 2.55 (6 H, m), 2.66 to 2.96 (3 H, m), 3. 94 (2H, s), 7.09-7. 18 (4H, m), 8.06 (1 H, s).

  The compounds of Example 273 and Example 274 shown in the following Table were produced in the same manner as in Example 272 using the corresponding starting materials.

Example 275
(S) -1- (2-Chloro-4-nitroimidazol-1-yl) -2-methyl-3- (4-phenyl-1,2,3,6-tetrahydropyridin-1-yl) propane-2 Preparation of 4-ol 4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride (0.495 g, 2.53 mmol) extracted with methylene chloride and aqueous sodium hydroxide solution, dried over sodium sulfate and filtered did. The filtrate was concentrated under reduced pressure and the concentrate was prepared from (R) -2-chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitroimidazole (0.5 g, 29 mmol) and 5 ml of DMF were added and stirred at 70 ° C. for 5 hours. The reaction mixture was extracted twice with ethyl acetate, then the organic phases were combined, washed with water and saturated brine, dried over sodium sulfate and filtered. The obtained filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (n-hexane / ethyl acetate = 2/1) to give (S) -1- (2-chloro-4) as a yellow oil. -Nitroimidazol-1-yl) -2-methyl-3- (4-phenyl-1,2,3,6-tetrahydropyridin-1-yl) propan-2-ol (0.492 g, yield 57%) I got
¹ H-NMR (CDCl ₃ ) δ ppm:
1.17 (3 H, s), 2.47 (1 H, d, J = 13.91 Hz), 2.58-2.64 (3 H, m), 2.78-3.00 (2 H, m), 3.27-3.40 (2H, m), 3.62 (1H, br), 4.01 (2H, s), 6.02-6. 05 (1 H, m), 7.23-7. 41 (5 H, m), 8.07 (1 H, s).

Example 276
Preparation of (S) -1- (2-Chloro-4-nitroimidazol-1-yl) -2-methyl-3- (4-phenylpiperidin-1-yl) propan-2-ol 4-phenylpiperidine hydrochloride (0.522 g, 2.64 mmol) was extracted with methylene chloride and aqueous sodium hydroxide, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and the concentrate was prepared from (R) -2-chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitroimidazole (0.5 g, 29 mmol) and 5 ml of DMF were added and stirred at 70 ° C. for 5 hours. After extraction twice with ethyl acetate, the organic phases were combined, washed with water and saturated brine, dried over sodium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (n-hexane / ethyl acetate = 2/1) to give (S) -1- (2-chloro-4-nitroimidazol-1-yl) -2-methyl as a yellow oil. -3- (4-phenylpiperidin-1-yl) propan-2-ol (0.703 g, 81% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.14 (3 H, s), 1.76 to 1.89 (4 H, m), 2.36 (1 H, d, J = 13.9 Hz), 2.48 to 2.61 (4 H, m), 2.75-2.89 (1H, m), 2.98-3.09 (1H, m), 3.75 (1H, br), 3.98 (2H, s), 7.18-7. 35 (5 H, m), 8.08 (1 H, s).

Example 277
(S) -1- (2-Chloro-4-nitroimidazol-1-yl) -2-methyl-3- [4- (4-trifluoromethylphenyl) piperidin-1-yl] propan-2-ol Preparation (R) -2-Chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitroimidazole (0.329 g, 1.51 mmol) prepared in Example 12 and 4- (4-) Trifluoromethylphenyl) piperidine (0.400 g, 1.66 mmol) was dissolved in 5 ml DMF and stirred at 70 ° C. for 3 hours. After extraction twice with ethyl acetate, the organic phases were combined, washed with water and saturated brine, dried over sodium sulfate and filtered. The obtained filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (n-hexane / ethyl acetate = 2/1) to give (S) -1- (2-chloro-4) as a brown oil. -Nitroimidazol-1-yl) -2-methyl-3- [4- (4-trifluoromethylphenyl) piperidin-1-yl] propan-2-ol (0.361 g, yield 54%) was obtained .
¹ H-NMR (CDCl ₃ ) δ ppm:
1.13 (3 H, s) 1.71-1. 93 (4 H, m), 2.36 (1 H, d, J = 14.0 Hz), 2.48-2.65 (4 H, m), 2 .77-2.90 (1 H, m), 3.01-3.14 (1 H, m), 3.64 (1 H, br), 3.99 (2 H, s), 7.32 (2 H, d) , J = 8.1 Hz), 7.57 (2 H, d, J = 8.1 Hz), 8.07 (1 H, s).

Example 278
Preparation of (S)-{1- [3- (2-Chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] piperidin-4-yl} carbamic acid tert-butyl ester Example EXAMPLE 2 277 Using (R) -2-Chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitroimidazole and piperidin-4-yl-carbamic acid tert-butyl ester prepared in Example 12 Similarly, (S)-{1- [3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] piperidin-4-yl} carbamine as a yellow oil An acid tert-butyl ester (yield 92%) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.11 (3 H, s), 1.32-1.51 (2 H, m), 1. 44 (9 H, m), 1.90-1. 96 (2 H, m), 2. 32 (1 H, 1 H, m) d, J = 13.9 Hz), 2.39-2.55 (2H, m), 2.46 (1 H, d, J = 13.9 Hz), 2.67-2.96 (3 H, m), 3.44 (1 H, br), 3.59 (1 H, s), 3.96 (2 H, s), 8.05 (1 H, s).

Example 279
(S)-{1- [3- (2-Chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methyl-propyl] piperidin-4-yl} -N- [2- (4- (4-) Preparation of trifluoromethylphenyl) ethyl] carbamic acid tert-butyl ester (R) -2-chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitroimidazole (0) prepared in Example 12 Implementation with .332 g (0.891 mmol) and piperidin-4-yl-N- [2- (4-trifluoromethylphenyl) ethyl] carbamic acid tert-butyl ester (0.194 g, 0.891 mmol) By a method similar to Example 277, (S)-{1- [3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methy] as a slightly yellow oil. Le-propyl] piperidin-4-yl} -N- [2- (4-trifluoromethylphenyl) ethyl] carbamic acid tert-butyl ester (0.370 g, 70% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.12 (3 H, s), 1.49 (9 H, s), 1.55 to 1.80 (4 H, m), 2.17 to 2.57 (4 H, m), 2.70-2. 98 (4H, m), 3.21-3.30 (2H, m), 3.50 (1 H, s), 3.95 (2 H, s), 7.31 (2 H, d, J = 8. 2 Hz), 7.57 (2 H, d, J = 8.2 Hz), 8.05 (1 H, s).

Example 280
Preparation of (S) -2-Methyl-6-nitro-2- [4- (4-trifluoromethylphenoxy) piperidin-1-ylmethyl] -2,3-dihydroimidazo [2,1-b] oxazole Example (S) -1- (2-Chloro-4-nitroimidazol-1-yl) -2-methyl-3- [4- (4-trifluoromethylphenoxy) piperidin-1-yl] propane-prepared according to The 2-ol (1.06 g, 2.3 mmol) was dissolved in 15 ml DMF. To this solution was added sodium hydride (110 mg, 2.76 mmol) under ice-cooling, and the mixture was stirred overnight at room temperature. The reaction solution was poured into water and extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 5/1) and crystallized from methylene chloride-diisopropyl ether to give (S) -2- (white powder) Methyl-6-nitro-2- [4- (4-trifluoromethylphenoxy) piperidin-1-ylmethyl] -2,3-dihydroimidazo [2,1-b] oxazole (431 mg, yield 44%) is obtained. The
MS 427 (M + 1) ⁺
Optical purity 97.8% ee
[Α] _D ²⁷ = -2.07 ° (concentration: 1.064, CHCl ₃ )
¹ H-NMR (CDCl ₃ ) δ ppm:
1.61 (3 H, s), 1.67-1.92 (4 H, m), 2.41-2.51 (1 H, m), 2.57 (1 H, d, J = 14.9 Hz), 2.58-2.67 (1 H, m), 2.88 (1 H, d, J = 14.9 Hz), 2.74-2.98 (2 H, m), 3.91 (1 H, d, J = 9.7 Hz), 4.31 (1 H, d, J = 9.7 Hz), 4.28-4.36 (1 H, m), 6.91 (2 H, d, J = 8.7 Hz), 7 .51 (2H, d, J = 8.7 Hz), 7.54 (1 H, s).

Example 281
Preparation of (S) -2-Methyl-6-nitro-2- [4- (4-trifluoromethylbenzyloxy) piperidin-1-ylmethyl] -2,3-dihydroimidazo [2,1-b] oxazole (S) -1- (2-Chloro-4-nitroimidazol-1-yl) -2-methyl-3- [4- (4-trifluoromethylbenzyloxy) piperidin-1-yl] prepared in Example 254 Propan-2-ol (1.36 g, 2.8 mmol) was dissolved in 15 ml DMF. To this solution was added sodium hydride (134 mg, 3.36 mmol) under ice cooling, and the mixture was stirred at room temperature overnight. The reaction solution was poured into water and extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 10/1) and crystallized from methylene chloride-diisopropyl ether to give (S) -2- (white powder) Methyl-6-nitro-2- [4- (4-trifluoromethylbenzyloxy) piperidin-1-ylmethyl] -2,3-dihydroimidazo [2,1-b] oxazole (431 mg, yield 44%) Obtained.
MS 440 (M-1) ⁺
91-92 ° C melting point
Optical purity 99.6% ee
[Α] _D ²⁷ = −8.63 ° (concentration: 1.066, CHCl ₃ )
¹ H-NMR (CDCl ₃ ) δ ppm:
1.44-1.66 (2H, m), 1.60 (3H, s), 1.71-1.85 (2H, m), 2.28-2.38 (1 H, m), 44-2.56 (1 H, m), 2.52 (1 H, d, J = 14.9 Hz), 2.72-2.81 (1 H, m), 2.84 (1 H, d, J = 14) .9 Hz), 2.87-2.94 (1 H, m), 3.33-3.41 (1 H, m), 3.88 (1 H, d, J = 9.6 Hz), 4.31 (1 H) , D, J = 9.6 Hz), 4.54 (2 H, s), 7.41 to 7.44 (2 H, m), 7.52 (1 H, s), 7.56 to 7.60 (2 H) , M).

Example 282
Preparation of (S) -2- [4- (4-Trifluoromethoxyphenyl) aminopiperidin-1-yl] methyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole (S) -1- (2-Chloro-4-nitroimidazol-1-yl) -2-methyl-3- [4- (4-trifluoromethoxyphenylamino) piperidin-1-yl prepared in Example 266 Similarly to Example 281 using propan-2-ol, (S) -2- [4- (4-trifluoromethoxyphenyl) aminopiperidin-1-yl] methyl-2-methyl- in a white powder. 6-Nitro-2,3-dihydroimidazo [2,1-b] oxazole (yield 73%) was obtained.
Melting point 107.5-109.0 ° C
MS 441 (M ⁺ )
Optical purity 99.8% ee
[Α] _D ²⁷ = 19.19 ° (concentration: 1.006, CHCl ₃ ).

Example 283
Preparation of (S)-[1- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperidin-4-yl] carbamic acid tert-butyl ester Tert-Butyl (S)-{1- [3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] piperidin-4-yl} carbamate prepared according to example 278 (S)-[1- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl] as a white powder using an ester in the same manner as in Example 281. ) Piperidin-4-yl] carbamic acid tert-butyl ester (yield 49%) was obtained.
MS 381 (M ⁺ )
Melting point 158.5-160.7 ° C.

Example 284
(S)-[1- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperidin-4-yl] -N- [2- (4- Preparation of trifluoromethylphenyl) ethyl] carbamic acid tert-butyl ester (S)-{1- [3- (2-Chloro-4-nitroimidazol-1-yl) -2-hydroxy- prepared in Example 279 Example 281 using 2-methyl-propyl] piperidin-4-yl} -N- [2- (4-trifluoromethylphenyl) ethyl] carbamic acid tert-butyl ester (0.37 g, 0.627 mmol) (S)-[1- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) in a pale yellow powdery crystal by the same method as in Piperidine-4-yl] -N- [2- (4-trifluoromethylphenyl) ethyl] carbamic acid tert-butyl ester (0.211 g, 63% yield) was obtained.
Mp 206.8-208.6 ° C.

Example 285
(S) -2-Methyl-6-nitro-2- {4- [4- (trifluoromethoxyphenyl) sulfanyl] piperidin-1-ylmethyl} -2,3-dihydroimidazo [2,1-b] oxazole Preparation (S) -1- (2-Chloro-4-nitroimidazol-1-yl) -2-methyl-3-{[4- (4-trifluoromethoxyphenyl) sulfanyl] piperidine prepared in Example 271 A white powder of (S) -2-methyl-6-nitro-2- {4- [4- (trifluoromethoxyphenyl) sulfanyl in the same manner as in Example 281 using 1-yl} propan-2-ol ] -Piperidin-1-ylmethyl} -2,3-dihydroimidazo [2,1-b] oxazole (yield 62%) was obtained.
MS 458 (M ⁺ )
Melting point 133.0-137.4 ° C.

Example 286
Preparation of (S) -2-Methyl-6-nitro-2- [4- (4-trifluoromethoxybenzyl) piperidin-1-yl] methyl-2,3-dihydroimidazo [2,1-b] oxazole (S) -1- (2-Chloro-4-nitroimidazol-1-yl) -2-methyl-3- [4- (4-trifluoromethoxybenzyl) piperidin-1-yl] propane prepared in Example 272 White powder of (S) -2-methyl-6-nitro-2- [4- (4-trifluoromethoxybenzyl) piperidin-1-yl] methyl in the same manner as in Example 281 using -2-ol -2,3-dihydro imidazo [2, 1-b] oxazole (yield 55%) was obtained.
111.0-112.5 ° C
MS: 440 (M ⁺ )
Optical purity 99.0% ee
^{_{[Α] D 27 = 5.38 °}} ( concentration: 1.004, CHCl _3).

Example 287
(S) -2-Methyl-6-nitro-2- (4-phenyl-1,2,3,6-tetrahydropyridin-1-ylmethyl) -2,3-dihydroimidazo [2,1-b] oxazole Preparation (S) -1- (2-Chloro-4-nitroimidazol-1-yl) -2-methyl-3- (4-phenyl-1,2,3,6-tetrahydropyridine) prepared in Example 275 1-yl) propan-2-ol (0.492 g, 1.31 mmol) was dissolved in 8 ml DMF and cooled to 4 ° C. To this solution was added sodium hydride (63 mg, 1.57 mmol) and stirred at room temperature for 3 hours. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate, then the organic phases were combined, washed with water and saturated brine, dried over sodium sulfate and filtered. The obtained filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (n-hexane / acetone = 4/1) and then recrystallized from methylene chloride and ethyl acetate to obtain a slightly yellow solid (S) -2-Methyl-6-nitro-2- (4-phenyl-1,2,3,6-tetrahydropyridin-1-ylmethyl) -2,3-dihydroimidazo [2,1-b] oxazole (0.059 g) , Yield 13%).
Mp 200.1-201 ° C.

Example 288
Preparation of (S) -2-Methyl-6-nitro-2- (4-phenylpiperidin-1-ylmethyl) -2,3-dihydroimidazo [2,1-b] oxazole Prepared as in Example 276 (S) -1- (2-chloro-4-nitroimidazol-1-yl) -2-methyl-3- (4-phenylpiperidin-1-yl) propan-2-ol (0.703 g, 1.86 mmol) It was dissolved in 12 ml DMF and cooled to 4 ° C. To this solution was added sodium hydride (89 mg, 2.23 mmol) and stirred at room temperature for 3 hours. Water was added to the reaction solution, and the precipitate was collected by filtration. The precipitate is purified by silica gel column chromatography (n-hexane / acetone = 3/1) and recrystallized from ethyl acetate to give (S) -2-methyl-6-nitro-2- (4-) as white powder crystals. Phenylpiperidin-1-ylmethyl) -2,3-dihydroimidazo [2,1-b] oxazole (0.230 g, 36% yield) was obtained.
Melting point 158.8-163.9 ° C.

  The compounds of Example 289 to Example 294 were produced in the same manner as in Example 288, using the corresponding starting materials.

Example 289
(S) -1 '-(2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl)-[1,4'] bipiperidinyl melting point 163.4-146. 9 ° C.

Example 290
(S) -2-Methyl-6-nitro-2- [4- (4-trifluoromethylphenyl) piperidin-1-ylmethyl] -2,3-dihydroimidazo [2,1-b] oxazole melting point 138.7 -139.9 ° C.

Example 291
(S) -2-Methyl-6-nitro-2- [4- (3-phenyl-2-propenyloxy) piperidin-1-ylmethyl] -2,3-dihydroimidazo [2,1-b] oxazole melting point 91 3-92.7 ° C.

Example 292
(S) -2- {4- [3- (4-chlorophenyl) -2-propenyloxy] piperidin-1-ylmethyl} -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b Mp 140.6-142.8 ° C.

Example 293
(S) -2-Methyl-6-nitro-2- {4- [2- (4-trifluoromethylphenyl) ethoxy] piperidin-1-ylmethyl} -2,3-dihydroimidazo [2,1-b] Oxazole mp 84.6-86.8 ° C.

Example 294
(S) -2- {4- [2- (4-Chlorophenyl) ethoxy] piperidin-1-ylmethyl} -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole melting point 92 5-94 ° C.

Example 295
(S)-[1- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperidin-4-yl] -N-methyl- (4-tri) Preparation of fluoromethoxyphenyl) amine (S) -2- [4- (4-Trifluoromethoxyphenyl) aminopiperidin-1-yl] methyl-2-methyl-6-nitro-2,3 prepared in Example 282 -Dissolve dihydroimidazo [2,1-b] oxazole (400 mg, 0.90 mmol) in 10 ml of methanol, 37% formaldehyde solution (0.13 ml, 4.52 mmol), sodium cyanoborohydride (170 mg, 2.71 mmol) and acetic acid (0.17 ml, 2.71 mmol) were added and stirred for 30 minutes at room temperature. The reaction mixture was poured into saturated aqueous sodium hydrogen carbonate solution and extracted with methylene chloride. The organic phase was dried over magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / methanol = 100/1) and recrystallized from methylene chloride-diisopropyl ether to give (S)-[1- (2-methyl-6) as pale yellow needles. -Nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperidin-4-yl] -N-methyl- (4-trifluoromethoxyphenyl) amine (309 mg, yield 78%) I got
Optical purity 99.9% ee
[Α] _D ¹⁷ = 7.77 ° (concentration: 1.042, CHCl ₃ )
MS 455 (M ⁺ )
Melting point 133.2-134.4 ° C.

Example 296
(S) -N- [1- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperidin-4-yl] -N- (4-tri Preparation of fluoromethoxyphenyl) acetamide (S) -2- [4- (4-Trifluoromethoxyphenyl) aminopiperidin-1-yl] methyl-2-methyl-6-nitro-2,3 prepared in Example 282 Dihydroimidazo [2,1-b] oxazole (153 mg, 0.35 mmol) was dissolved in 5 ml of methylene chloride, 76 μl of triethylamine and 30 μl of acetyl chloride were added and stirred for 1.5 hours at room temperature. The reaction solution was poured into water and extracted with methylene chloride. The organic phase was dried over magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / methanol = 100/1) and crystallized from methylene chloride-diisopropyl ether to give (S) -N- [1- (2-methyl-6-nitro) as a white powder. -2,3-dihydro imidazo [2, 1-b] oxazol -2- ylmethyl) piperidin- 4-yl] -N- (4- trifluoro methoxyphenyl) acetamide (82 mg, yield 49%) was obtained.
MS 484 (M + 1) ⁺
Melting point 137.0-138.7 ° C.

Example 297
(S) -2- {4-N-[(4-trifluoromethylphenyl) acetyl] aminopiperidin-1-yl} methyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-] b) Preparation of oxazole (S)-[1- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperidine-4- 4 prepared in Example 283 [I]] carbamic acid tert-butyl ester (0.1 g, 0.262 mmol) was dissolved in 4 ml of ethanol, 3 ml of 6 N hydrochloric acid was added, and the mixture was stirred at room temperature for 5 hours. The reaction mixture was concentrated under reduced pressure, 4 ml of methylene chloride and 4 ml of triethylamine were added to the concentrate, and the mixture was stirred at room temperature for 5 minutes and concentrated. Water was azeotroped by adding 10 ml of toluene and concentrating. The concentrated solution contains 4-trifluoromethylphenylacetic acid (0.064 g, 0.315 mmol), 4 ml of methylene chloride, triethylamine (0.06 ml, 0.393 mmol) and 1-ethyl-3- (3-dimethylaminopropyl) Carbodiimide hydrochloride (WSCD) (0.065 g, 0.341 mmol) was added and stirred overnight at room temperature. Water was added to the reaction solution, and the mixture was extracted twice with methylene chloride, and then the organic phases were combined, washed with water and saturated brine, dried over sodium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane / acetone = 3/2. Recrystallization from 3 ml of ethyl acetate) gave (S) -2- {4-N-[(4-trifluoromethyl) as white powder crystals. Phenyl) acetyl] aminopiperidin-1-yl} methyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole (32 mg, 26% yield) was obtained.
Melting point 152.7-154.3 [deg.] C.

Example 298
(S)-[1- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperidin-4-yl] carbamic acid 4-trifluoromethylbenzyl ester Preparation of (S)-[1- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperidin-4-yl] carbamine prepared in Example 283 Acid tert-butyl ester (0.300 g, 0.787 mmol) was dissolved in 4 ml of methylene chloride, 2 ml of trifluoroacetic acid was added and stirred for 2 hours at room temperature. The reaction solution was concentrated under reduced pressure, and 4 ml each of methylene chloride and triethylamine were added. The mixture was stirred at room temperature for 5 minutes and then concentrated under reduced pressure. The residue was dissolved in 6 ml DMF. In this solution 4- (trifluoromethyl) benzyl alcohol (0.166 g, 0.944 mmol) is dissolved in 4 ml DMF and 1,1'-carbonyldiimidazole (0.153 g, 0.944 mmol) is added The mixture stirred at room temperature for 4 hours was added. The mixture was stirred at room temperature overnight and then at 65 ° C. for 8 hours. Water was added to the reaction solution, and the mixture was extracted twice with ethyl acetate, then the organic phases were combined, washed with water and saturated brine, dried over sodium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane / acetone = 2/1). Recrystallization from ethyl acetate, filtration and drying under reduced pressure give (S)-[1- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] of pale yellow powder crystals. Oxazol-2-ylmethyl) piperidin-4-yl] carbamic acid 4-trifluoromethylbenzyl ester (0.107 g, yield 28%) was obtained.
Melting point 141.2-144 [deg.] C.

  The compounds of Example 299 and Example 300 were produced in the same manner as in Example 298, using the corresponding starting materials.

Example 299
(S)-[1- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperidin-4-yl] carbamic acid 1- (4-trifluoro Methylphenyl) piperidin-4-yl ester mp 134.4-136.9 ° C.

Embodiment 300
(S)-[1- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperidin-4-yl] carbamic acid 4-trifluoromethoxybenzyl ester Mp 156.2-158.5 ° C.

Example 301
(S)-[1- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperidin-4-yl]-(4-trifluoromethylbenzyl) Preparation of Amines (S)-[1- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperidin-4-yl] prepared in Example 283 Carbamic acid tert-butyl ester (0.300 g, 0.787 mmol) was dissolved in 4 ml of methylene chloride, 2 ml of trifluoroacetic acid was added and stirred at room temperature for 1 hour. The reaction solution was concentrated under reduced pressure, and 4 ml each of methylene chloride and triethylamine were added. The mixture was stirred at room temperature for 20 minutes and then concentrated under reduced pressure. The residue is dissolved in 4 ml of methanol, into which 4-trifluoromethylbenzaldehyde (0.164 g, 0.945 mmol), sodium cyanotrihydroborate (0.099 g, 1.57 mmol) and acetic acid (0.09 ml) are added. 1.57 mmol) was added and stirred at room temperature for 4 hours. The reaction mixture was concentrated under reduced pressure, water was added to the residue, and the mixture was extracted with methylene chloride. The organic phases were combined, washed with brine, dried over sodium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride / methanol = 20/1). It is recrystallized from isopropyl alcohol, filtered and dried under reduced pressure to obtain (S)-[1- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] of slightly yellow powdery crystals. Oxazol-2-ylmethyl) piperidin-4-yl]-(4-trifluoromethylbenzyl) amine (0.078 g, 22% yield) was obtained.
Melting point 148.6-152.9 [deg.] C.

Example 302
(S) -1- [1- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperidin-4-yl] -3- (4-tri Preparation of fluoromethylphenyl) urea (S)-[1- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperidine prepared in Example 283 4-yl] carbamic acid tert-butyl ester (0.300 g, 0.787 mmol) was dissolved in 4 ml of methylene chloride, 2 ml of trifluoroacetic acid was added and stirred for 2 hours at room temperature. After concentration under reduced pressure, 4 ml of methylene chloride and triethylamine were added, and the mixture was stirred at room temperature for 5 minutes and then concentrated under reduced pressure. Let this be "residue 1".

  On the other hand, 4- (trifluoromethyl) aniline (0.139 g, 0.865 mmol) is dissolved in 4 ml of THF, pyridine (0.07 ml, 0.865 mmol) is added, and phenyl chloroformate (0. 108 ml (0.865 mmol) was added and reacted at room temperature for 1 hour. The reaction mixture was diluted with ethyl acetate, washed with water, 10% hydrochloric acid and saturated brine, dried over sodium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure.

The residue obtained is dissolved in 6 ml of dimethyl sulfoxide. This was added to the above-mentioned "residue 1" and stirred overnight at room temperature. Water was added to the reaction solution, and the mixture was extracted twice with ethyl acetate, then the organic phases were combined, washed with water, saturated aqueous sodium bicarbonate solution and saturated brine, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (n-hexane / acetone = 2/1). Recrystallization from 6 ml of isopropyl alcohol / n-hexane (1/1), filtration and drying under reduced pressure give (S) -1- [1- (2-methyl-6-nitro-2) as a slightly yellow powder crystal. 3, 3-Dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperidin-4-yl] -3- (4-trifluoromethylphenyl) urea (0.064 g, 17% yield) was obtained.
Melting point 136.8-139.9 ° C.

Example 303
(S) -2- [4-N- (4-Trifluoromethylbenzoyl) aminopiperidin-1-yl] methyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole Preparation of (S)-[1- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperidin-4-yl] carbamine prepared in Example 283 Acid tert-butyl ester (360 mg, 0.92 mmol) was dissolved in 5 ml of methylene chloride, 5 ml of trifluoroacetic acid was added and stirred for 5 hours at room temperature. The reaction mixture was concentrated under reduced pressure, 10 ml of methylene chloride and 2 ml of triethylamine were added, followed by 4-trifluoromethylbenzoyl chloride (0.3 ml, 1.85 mmol), and the mixture was stirred at room temperature for 1 hour. The reaction solution was poured into water and extracted with methylene chloride. The organic phase was washed with brine, dried over magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (methylene chloride / methanol = 20/1). Crystallization is carried out from ethyl acetate-diisopropyl ether, followed by filtration and drying under reduced pressure to obtain (S) -2- [4-N- (4-trifluoromethylbenzoyl) aminopiperidin-1-yl] methyl as white powder. 2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole (232 mg, 55% yield) was obtained.
MS 454 (M + H) ⁺
Mp 170.5-171.7 ° C.

Example 304
(S)-[1- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperidin-4-yl]-[2- (4-trifluoro] Preparation of methylphenyl) ethyl] amine (S)-[1- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperidine prepared in Example 284 4-yl] -N- [2- (4-trifluoromethylphenyl) ethyl] carbamic acid tert-butyl ester (0.196 g, 0.354 mmol) is dissolved in 2 ml of methylene chloride and 1 ml of trifluoroacetic acid Add and stir at room temperature for 4 hours. Saturated aqueous sodium bicarbonate was added to the reaction solution, and the mixture was extracted twice with methylene chloride. The organic phases were combined, dried over sodium sulfate and filtered. The filtrate is concentrated under reduced pressure, and the obtained residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 10/1), solidified by adding isopropyl ether, filtered and dried under reduced pressure. (S)-[1- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperidin-4-yl]-[2- (yellow) powder crystal in yellow powder 4-Trifluoromethylphenyl) ethyl] amine (0.020 g, 12% yield) was obtained.
Mp 80.7-84.2 ° C.

Example 305
(S) -2-Methyl-6-nitro-2- {4- [4- (trifluoromethoxy) benzenesulfinyl] piperidin-1-ylmethyl} -2,3-dihydroimidazo [2,1-b] oxazole Preparation (S) -2-Methyl-6-nitro-2- {4- [4- (trifluoromethoxyphenyl) sulfanyl] piperidin-1-ylmethyl} -2,3-dihydroimidazo [2] prepared in Example 285 1,1-b] oxazole (300 mg, 0.65 mmol) was dissolved in 5 ml of methylene chloride. To this solution was added m-chloroperbenzoic acid (169 mg, 0.69 mmol) and stirred at room temperature for 30 minutes. The reaction mixture was diluted with methylene chloride, washed with aqueous sodium thiosulfate solution, saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over sodium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride / methanol = 50/1) and crystallized from ethyl acetate-isopropyl ether. The crystals are collected by filtration and dried to give (S) -2-methyl-6-nitro-2- {4- [4- (trifluoromethoxy) benzenesulfinyl] piperidin-1-ylmethyl} -2 as a white powder. 3, 3-dihydroimidazo [2,1-b] oxazole (219 mg, 71% yield) was obtained.
MS 475 (M + H) ⁺
107-109 ° C.

Example 306
Preparation of 2- (4-tert-butoxycarbonylpiperazin-1-yl) methyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole 2-chloro-4-nitro-1H -Imidazole (3.19 g, 21.6 mmol) and 4- (2-methyl-2-oxiranylmethyl) piperazine-1-carboxylic acid tert-butyl ester (5.53 g, 21.6 mmol) and sodium acetate (1.95 g, 23.8 mmol) was dissolved in 50 ml of 1-propanol and heated to reflux for 48 hours. The reaction mixture was diluted with methylene chloride, washed with water and saturated brine, dried over sodium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride / methanol = 100/1), and then crystallized by adding methylene chloride-diisopropyl ether. After filtration and drying under reduced pressure, 2- (4-tert-butoxycarbonylpiperazin-1-yl) methyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] of white powdery crystals is obtained. Oxazole (1.85 g, 23% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.43 (9 H, s), 1.62 (3 H, s), 2.45-2.68 (5 H, m), 2.87 (1 H, d, J = 14.9 Hz), 3.30 ( 4H, br), 3.93 (1 H, d, J = 9.7 Hz), 4.30 (1 H, d, J = 9.7 Hz), 7.54 (1 H, s).

  The compound of Example 307 was produced in the same manner as in Example 306 using the corresponding starting materials.

Example 307
2- [4- (4-Cyanophenyl) piperazin-1-yl] methyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole yield 18%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.67 (3H, s), 2.60-2.80 (3H, m), 2. 80-3.00 (3H, m), 3.22 (4H, br), 3.97 (1H, m) d, J = 9.8 Hz), 4.35 to 4.50 (1 H, m), 6.78 to 6.85 (2 H, m), 7.46 to 7.51 (2 H, m), 7. 55 (1 H, s).

Example 308
Preparation of 2- [4- (4-trifluoromethylphenyl) piperazin-1-yl] methyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole 2-chloro-4 -Nitro-1H-imidazole (1.59 g, 10.8 mmol) and 1- (2-methyl-2-oxanylyl) -4- (4-trifluoromethylphenyl) piperazine (3.23 g, 10.8 mmol) Sodium hydrogen carbonate (1.95 g, 23.8 mmol) was added to a solution of (1) in 1-propanol (20 ml) and the mixture was heated to reflux overnight. The reaction solution was concentrated under reduced pressure, extracted with methylene chloride, dried over sodium sulfate and filtered. The filtrate is concentrated under reduced pressure, and the residue is separated and purified by silica gel column chromatography (methylene chloride / methanol = 100/1), crystallized with methylene chloride-isopropyl ether, and 2- [4 of pale yellow powder -(4-trifluoromethylphenyl) piperazin-1-yl] methyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole (1.34 g, yield 29%) Obtained.
MS 411 (M ⁺ )
Mp 159-160 ° C.

In addition, separation and purification by the above-mentioned silica gel column chromatography, the intermediate 2-chloro-1- {3- [4- (4-trifluoromethylphenyl) piperazin-1-yl] -2-hydroxy-2-methyl} is obtained. Propyl-4-nitroimidazole was obtained as a yellow oil (697 mg, 15% yield).
¹ H-NMR (CDCl ₃ ) δ ppm:
1.17 (3H, s), 2.32 to 2.91 (6H, s), 3.26 to 3.31 (4H, m), 4.03 (2H, s), 6.71 (1H, 1H, s) s), 6.89-6.93 (2H, m), 7.45-7.51 (2H, m), 8.06 (1 H, s).

  The compounds of Example 309 to Example 311 were produced in the same manner as in Example 308, using the corresponding starting materials.

Example 309
2- [4- (4-biphenylyl) piperazin-1-yl] methyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole yield 32%, mp 223-227. 8 ° C.

Example 310
2- [4- (4-chlorophenyl) piperazin-1-yl] methyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole yield 14%, melting point 196.6- 197.3 ° C.

Example 311
2- [4- (4-Trifluoromethoxyphenyl) piperazin-1-yl] methyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole yield 18%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.61 (3 H, s), 2.61 (1 H, d, J = 14.8 Hz), 2.65-2.73 (2 H, m), 2.82-2.95 (2 H, m), 2.93 (1 H, d, J = 14.8 Hz), 2.99-3.09 (4 H, m), 3.94 (1 H, d, J = 9.7 Hz), 4. 34 (1 H, d , J = 9.7 Hz), 6.78-6.86 (2H, m), 7.06-7.11 (2H, m), 7.53 (1 H, s).

Example 312
Preparation of 1- [3- (4-tert-butoxycarbonylpiperazin-1-yl) -2-hydroxy-2-methyl] propyl-2-chloro-4-nitroimidazole 2-chloro-4-nitro-1H-imidazole (863 mg, 5.85 mmol) and 4- (2-methyl-2-oxiranylmethyl) piperazine-1-carboxylic acid tert-butyl ester (1.5 g, 5.85 mmol)) in 1-propanol (10 m) The solution was heated to reflux for 6 hours. The reaction solution was returned to room temperature and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / methanol = 100/1) to give 1- [3- (4-tert-butoxycarbonylpiperazin-1-yl) -2-hydroxy-2-methyl of white powdery crystals. ] Propyl-2-chloro-4-nitroimidazole (705 mg, 29.8% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.15 (3 H, s), 1. 45 (9 H, s), 2. 35 (1 H, d, J = 13.9 Hz), 2.45-2.65 (5 H, m), 3.25 ( 1 H, s), 3.42 (4 H, t, J = 4.3 Hz), 4.00 (2 H, s), 8.05 (1 H, s).

  2-Chloro-4-nitro-1H-imidazole and 4- (2-oxiranylmethyl) piperazine-1-carboxylic acid tert-butyl ester, 4- [2- (2-methyl-2-oxiranyl) ethyl] piperazine Examples 313 to 315 Analogously to Example 312 using 1-carboxylic acid tert-butyl ester or 4- (2-methyl-2-oxiranylmethyl) piperazine-1-carboxylic acid benzyl ester The compound of

Example 313
4- [3- (2-Chloro-4-nitroimidazol-1-yl) -2-hydroxypropyl] piperazine-1-carboxylic acid tert-butyl ester slightly yellow powder crystal, yield 43%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.46 (9H, s), 2.16 to 2.50 (4H, m), 2.55 to 2.70 (2H, m), 3. 40 to 3.51 (4H, m), 3. 64 (1 H, s), 3.91-4.09 (2 H, m), 4. 17 (1 H, dd, J = 2.0 Hz, 13.5 Hz), 8.00 (1 H, s).

Example 314
4- [4- (2-Chloro-4-nitroimidazol-1-yl) -3-hydroxy-3-methylbutyl] piperazine-1-carboxylic acid tert-butyl ester white powder, 17% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
1.23 (3H, s), 1.40 to 1.74 (11 H, m), 2.23 to 2.58 (5 H, m), 2.81 to 2.95 (1 H, m), 26-3.51 (4H, m), 3.91 (1 H, d, J = 14.0 Hz), 3.99 (1 H, d, J = 14.0 Hz), 6.94 (1 H, s), 8.07 (1 H, s).

Example 315
4- [3- (2-Chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] piperazine-1-carboxylic acid benzyl ester slightly yellow oil, yield 81%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.14 (3H, s), 2.35-2.76 (6H, m), 3.43-3.61 (4H, m), 4.01 (2H, s), 5.13 (2H, 2H, s) s), 7.28-7. 43 (5 H, m), 8.04 (1 H, s).

Example 316
Preparation of 4- [3- (2-Chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] piperazine-1-carboxylic acid isobutyl ester 1- [3-prepared as described in Example 312 A mixture of (4-tert-butoxycarbonylpiperazin-1-yl) -2-hydroxy-2-methyl] propyl-2-chloro-4-nitroimidazole (150 mg, 0.37 mmol) and trifluoroacetic acid (5 ml) Stir at room temperature for 5 hours. The reaction solution was concentrated under reduced pressure. The residue was dissolved in methylene chloride (5 ml), triethylamine (0.23 ml, 1.63 mmol) and isobutyl chloroformate (112 mg, 0.82 mmol) were added in this order and stirred for 30 minutes at room temperature. The reaction solution was washed successively with water, saturated aqueous sodium bicarbonate solution and saturated brine, dried over magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to give 4- [3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] piperazine-1-carboxylic acid isobutyl ester. This was carried forward to the next step without purification.
¹ H-NMR (CDCl ₃ ) δ ppm:
0.93 (6 H, d, J = 6.7 Hz), 1.14 (3 H, s), 1.82-2.00 (1 H, m), 2.39 (1 H, d, J = 13.9 Hz ), 2.47-2.73 (5H, m), 3.11 (1H, d, J = 7.3 Hz), 3.17 (1 H, d, J = 7.3 Hz), 3.41-3. .55 (4 H, m), 3.87 (2 H, s), 4.04 (1 H, s), 8. 10 (1 H, s).

Example 317
Preparation of 4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid benzyl ester 4- [3 prepared in Example 315 -(2-Chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] piperazine-1-carboxylic acid benzyl ester (55.22 g, 126.11 mmol) and 1,4-dioxane Sodium hydride (6.05 g, 151.25 mmol) was added to the mixture of 550 ml) and heated to reflux for 14 hours. The reaction solution was returned to room temperature and concentrated under reduced pressure. Water was added to the residue, and the mixture was extracted twice with methylene chloride, washed with saturated brine, dried over magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (ethyl acetate) to give 4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole- of white powdery crystals. 2-ylmethyl) piperazine-1-carboxylic acid benzyl ester (26.54 g, 52% yield) was obtained.
Melting point 130.5-132.1 ° C
¹ H-NMR (CDCl ₃ ) δ ppm:
1.61 (3H, s), 2.38-2.69 (5H, m), 2.86 (1 H, d, J = 14.8 Hz), 3.10-3.50 (4 H, m), 3.92 (1 H, d, J = 9.9 Hz), 4.33 (1 H, d, J = 9.9 Hz), 5.11 (2 H, s), 7.23 to 7.38 (5 H, m) ), 7.53 (1 H, s).

  The compounds of Example 318 to Example 320 were produced in the same manner as in Example 317, using the corresponding starting materials.

Example 318
4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid isobutyl ester slightly yellow powder crystal, yield 39%, melting point 176 5-177.3 ° C.

Example 319
4- (6-Nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid tert-butyl ester white powder crystal, yield 45%, melting point 185-188 ° C (Disassembly)
¹ H-NMR (CDCl ₃ ) δ ppm:
1.45 (9H, s), 2.48-2.58 (4H, m), 2.85 (2H, d, J = 5.1 Hz), 3.31-3.45 (4H, m), 4.20 (1H, dd, J = 6.9 Hz, 10.3 Hz), 4.34 (1 H, dd, J = 8.4 Hz, 10.3 Hz), 5.35 to 5.48 (1 H, m) , 7.55 (1 H, s).

Example 320
4- [2- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-yl) ethyl] piperazine-1-carboxylic acid tert-butyl ester slightly yellow powder, 70%, melting point 190-191 DEG C. (decomposition).

Example 321
Preparation of 4- [3- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-yl) propyl] piperazi-1-carboxylic acid tert-butyl ester Example 39 Prepared methanesulfonic acid 3- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-yl) propyl ester (2 g, 6.6 mmol), piperazine-1 -A mixture of carboxylic acid tert-butyl ester (1.4 g, 7.5 mmol), triethylamine (1.3 g, 12.85 mmol), potassium iodide (1.8 g, 10.8 mmol) and DMF (15 ml) The mixture was stirred at 60 ° C. overnight. The reaction solution was cooled to room temperature, water was added, and the mixture was extracted three times with ethyl acetate. The organic phases were combined, washed twice with water, then washed with saturated brine, dried over sodium sulfate and filtered. The filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (methylene chloride / methanol = 20/1) to give 4- [3- (2-methyl-6-nitro-2,3-] as a white powder. Dihydroimidazo [2,1-b] oxazol-2-yl) propyl] piperazi-1-carboxylic acid tert-butyl ester (1.9 g, 73% yield) was obtained.
Melting point 166-167 [deg.] C.

Example 322
Preparation of 2-Methyl-6-nitro-2- (piperazin-1-ylmethyl) -2,3-dihydroimidazo [2,1-b] oxazole dihydrochloride 2- (4-tert) prepared in Example 306 -Butoxycarbonylpiperazin-1-yl) methyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole (1, 19 g, 3.24 mmol) in trifluoroacetic acid (30 ml) And stirred for 3 hours at room temperature. The reaction solution was concentrated under reduced pressure, the residue was dissolved in methanol (30 ml) and stirred with ice cooling. A solution of hydrogen chloride in ethyl acetate was added little by little and stirred at the same temperature for 30 minutes. The precipitated crystals are collected by filtration to give yellow powder of 2-methyl-6-nitro-2- (piperazin-1-ylmethyl) -2,3-dihydroimidazo [2,1-b] oxazole dihydrochloride (1. 06 g, 96% yield) were obtained.
¹ H-NMR (DMSO-d ₆ ) δ ppm:
1.68 (3 H, s), 3.00 to 3.59 (6 H, m), 4. 14 (1 H, d, J = 11.1 Hz), 4.36 (1 H, d, J = 11.1 Hz) ), 4.50-6.12 (4 H, br), 8. 17 (1 H, s), 9. 62 (2 H, br).

Example 323
Preparation of 2- [4- (4-biphenylylmethyl) piperazin-1-ylmethyl] -6-nitro-2,3-dihydroimidazo [2,1-b] oxazole 4- (6-) prepared in Example 319 A mixture of nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid tert-butyl ester (400 mg, 1.13 mmol) and trifluoroacetic acid (10 ml) 4 Stir at room temperature for hours. The reaction solution was concentrated, the residue was dissolved in methylene chloride (10 ml) and triethylamine (2 ml, 14.35 mmol) was added to neutralize. The resulting solution is concentrated under reduced pressure and the residue is dissolved in methanol (10 ml), to which 4-phenylbenzaldehyde (515 mg, 2.83 mmol), sodium cyanoborohydride (214 mg, 3.41 mmol) ), Acetic acid (0.21 m, 3.67 mmol) in this order and stirred overnight at room temperature. The reaction solution was concentrated, water was added to the residue, and the mixture was extracted twice with methylene chloride. The organic phases were combined, washed successively with saturated aqueous sodium bicarbonate solution and saturated brine, dried over magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (methylene chloride / methanol = 20/1) to give 2- [4- (4-biphenylylmethyl) piperazin-1-ylmethyl] as a white powder. There was obtained -6-nitro-2,3-dihydroimidazo [2,1-b] oxazole (188 mg, 40% yield).
Melting point 183-185 [deg.] C (decomposition).

  The compounds of Example 324 to Example 329 were produced in the same manner as in Example 323, using the corresponding starting materials.

Example 324
2- {2- [4- (4-trifluoromethylbenzyl) piperazin-1-yl] ethyl} -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole white powder, Yield 36%, mp 148-149 ° C.

Example 325
2-Methyl-6-nitro-2- {3- [4- (4-trifluoromethylbenzyl) piperazin-1-yl] propyl} -2,3-dihydroimidazo [2,1-b] oxazole white powder, Yield 57%, mp 154-156 ° C.

Example 326
2- {2- [4- (4-biphenylylmethyl) piperazin-1-yl] ethyl} -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole white powder, 53%, melting point 181-182 ° C.

Example 327
2- {3- [4- (4-biphenylylmethyl) piperazin-1-yl] propyl} -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole white powder, 65%, melting point 176-178 ° C.

Example 328
4- (N, N-Dimethylamino) -4 '-[4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-ylmethyl ] Biphenyl white powder, yield 68%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.58 (3 H, s), 2.36 (4 H, br), 2.50-2. 60 (2 H, m), 2.54 (1 H, d, J = 14.8 Hz), 2.67- 2.76 (2H, m), 2.84 (1 H, d, J = 14.8 Hz), 2.99 (6 H, s), 3.41 (1 H, d, J = 12.9 Hz), 3. 48 (1 H, d, J = 12.9 Hz), 3.87 (1 H, d, J = 9.7 Hz), 4.30 (1 H, d, J = 9.7 Hz), 6.76-6.82 (2H, m), 7.25-7.29 (2H, m), 7.46-7.51 (4H, m), 7.53 (1 H, s).

Example 329
2-Methyl-6-nitro-2- [4- (2-phenyl-1H-imidazol-4-ylmethyl) piperazin-1-ylmethyl] -2,3-dihydroimidazo [2,1-b] oxazole white powder, 93% yield
¹ H-NMR (DMSO-d ₆ ) δ ppm:
1.52 (3 H, s), 2.10-2.64 (6 H, m), 2.67 (1 H, d, J = 15.4 Hz), 2.74 (1 H, d, J = 15.4 Hz) ), 3.10-3.70 (4H, br), 4.04 (1H, d, J = 10.7 Hz), 4.21 (1H, d, J = 10.7 Hz), 6.97 (1H) , Br), 7.27-7.34 (1 H, m), 7. 38-7. 45 (2 H, m), 7. 88-7. 93 (2 H, m), 8.12 (1 H, s). ).

Example 330
2- (3,4-Dichlorophenyl) -1- [4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] ethanone A mixture of 3,4- (dichlorophenyl) acetic acid (418 mg, 2.04 mmol) and thionyl chloride (3 ml) was heated to reflux for 6 hours. The reaction was concentrated under reduced pressure to give the corresponding acid chloride.

On the other hand, 2- (4-tert-butoxycarbonylpiperazin-1-yl) methyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole (300 mg, prepared in Example 306) A mixture of 0.816 mmol) and trifluoroacetic acid (6 ml) was stirred at room temperature for 6 hours. The reaction solution was concentrated under reduced pressure. The residue was dissolved in 10 ml of methylene chloride and triethylamine (2 ml, 14.35 mmol) was added. A solution of the acid chloride obtained above in 5 ml of methylene chloride was gradually added to this solution under ice-cooling and stirred for 30 minutes at room temperature. The reaction solution was washed successively with saturated aqueous sodium bicarbonate solution, water and saturated brine, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / methanol = 100/1) to give 2- (3,4-dichlorophenyl) -1- [4- (2-methyl-6-nitro-2, 3-Dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] ethanone (255 mg, yield 69%) was obtained.
Melting point 189-191 [deg.] C.

  The compounds of Example 331 and Example 332 were obtained in the same manner as in Example 330, using the corresponding starting materials.

Example 331
1- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] -2- (4-trifluoromethylphenyl) Ethanone melting point 168-171.4 ° C.

Example 332
2- (3,4-Dichlorophenoxy) -1- [4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] Ethanone melting point 209-211 [deg.] C.

Example 333
2- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] -N- (4-trifluoromethylphenyl) Preparation of Acetamide 2- (4-tert-Butoxycarbonylpiperazin-1-yl) methyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole (500 mg) prepared in Example 306 A mixture of 1.36 mmol) and trifluoroacetic acid (15 ml) was stirred overnight at room temperature. The reaction solution was concentrated under reduced pressure, the residue was dissolved in methylene chloride (10 ml) and triethylamine (2 ml, 14.35 mmol) was added to neutralize. The solution is concentrated under reduced pressure and the residue is dissolved in DMF (10 ml), to which 2-bromo-N- (4-trifluoromethylphenyl) acetamide (423 mg, 1.5 mmol), potassium carbonate (207 mg) , 1.5 mmol) and sodium iodide (204 mg, 1.36 mmol) were added and stirred for 5 hours at room temperature. Water was added to the reaction solution, and extracted twice with ethyl acetate. The organic phases were combined, washed three times with water, then washed with saturated brine, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / methanol = 100/1) to give 2- [4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] as a white powder. Oxazol-2-ylmethyl) piperazin-1-yl] -N- (4-trifluoromethylphenyl) acetamide (389 mg, yield 61%) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.62 (3 H, s), 2.53-2.84 (9 H, m), 2.88 (1 H, d, J = 14.8 Hz), 3.06 (1 H, d, J = 16.7 Hz ), 3.14 (1 H, d, J = 16.7 Hz), 3.93 (1 H, d, J = 9.7 Hz), 4.30 (1 H, d, J = 9.7 Hz), 7.55 (1H, s), 7.55-7.59 (2H, m), 7.65-7.71 (2H, m), 9.20 (1 H, s).

  The compounds of Example 334 to Example 336 were produced in the same manner as in Example 333 using the corresponding starting materials.

Example 334
[4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] acetic acid ethyl ester
¹ H-NMR (CDCl ₃ ) δ ppm:
1.25 (3 H, t, J = 7.1 Hz), 1.60 (3 H, s), 2.45-2.64 (6 H, m), 2.55 (1 H, d, J = 14.8 Hz ), 2.72-2.81 (2H, m), 2.87 (1H, d, J = 14.8 Hz), 3.14 (2H, s), 3.90 (1 H, d, J = 9) .7 Hz), 4.16 (2 H, q, J = 7.1 Hz), 4.31 (1 H, d, J = 9.7 Hz), 7.57 (1 H, s).

Example 335
3- {3- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] propyl} -3H-benzoxazole- 2-one mp 123-126 ° C.

Example 336
1- (4-Chlorophenyl) -2- [4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] ethanone
¹ H-NMR (CDCl ₃ ) δ ppm:
1.60 (3 H, s), 2.47 (4 H, br), 2.53 (1 H, d, J = 14.9 Hz), 2.57-2.65 (2 H, m), 2.74- 2.84 (2 H, m), 2.87 (1 H, d, J = 14.9 Hz), 3.64 (1 H, d, J = 16.7 Hz), 3.75 (1 H, d, J = 16) .7 Hz), 3.90 (1 H, d, J = 9.7 Hz), 4. 30 (1 H, d, J = 9.7 Hz), 7.42 (2 H, d, J = 8.6 Hz), 7 .54 (1 H, s), 7.92 (2 H, d, J = 8.6 Hz).

Example 337
Preparation of 4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid benzyl ester hydrochloride salt Prepared as in Example 306 2- (4-tert-Butoxycarbonylpiperazin-1-yl) methyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole (130 mg, 0.35 mmol), trifluoroacetic acid ( A mixture of 3 ml) and methylene chloride (5 ml) was stirred at room temperature for 1 hour. The reaction was concentrated under reduced pressure and the residue was dissolved in methylene chloride (5 ml) and triethylamine (107.5 mg, 1.06 mmol) was added. To this solution was added benzyl chloroformate (120 mg, 0.71 mmol) under ice-cooling, and the mixture was stirred at room temperature for 1 hour. The reaction solution was washed successively with water, saturated aqueous sodium bicarbonate solution and saturated brine, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride / methanol = 20/1) to give a yellow oil. The oil was dissolved in ethyl acetate (5 ml). A saturated solution of ethyl acetate in hydrochloric acid is added thereto, and the precipitated crystals are collected by filtration to give 4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole-2 as white powder crystals. -Ylmethyl) piperazine-1-carboxylic acid benzyl ester hydrochloride (46.8 mg, 30% yield) was obtained.
Melting point 130.5-132.1 ° C.

  The compounds of Examples 338 to 340 were produced in the same manner as in Example 337, using the corresponding starting materials.

Example 338
4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid phenyl ester mp 81-85 ° C.

Example 339
4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid isopropyl ester mp 158.3-159.8 ° C.

Example 340
4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid n-octyl ester mp 138-139.4 ° C.

Example 341
Preparation of 4- (6-Nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid 4-trifluoromethylbenzyl ester Dissolve 6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid tert-butyl ester (400 mg, 1.13 mmol) in methylene chloride (2 ml) Trifluoroacetic acid (1 ml) was added and stirred at room temperature for 1 hour. The reaction solution was concentrated under reduced pressure, the residue was dissolved in DMF (1 ml), and triethylamine (1 ml) was added for neutralization to obtain a neutralized solution.

  Meanwhile, 4-trifluoromethylbenzyl alcohol (297 mg, 1.69 mmol) is dissolved in DMF (1 ml), 1,1'-carbonyldiimidazole (274 mg, 1.69 mmol) is added, and 1 at room temperature. Stir for time to prepare the active ester.

The solution of this active ester was added to the above neutralization solution and stirred at room temperature for 3 hours. Water was added to the reaction solution and extracted twice with ethyl acetate. The organic phases were combined, washed twice with water, then washed with saturated brine, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / methanol = 20/1) to give 4- (6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl of pale yellow powdery crystals. )) Piperazine-1-carboxylic acid 4-trifluoromethylbenzyl ester (322 mg, 63% yield) was obtained.
Melting point 120-122 [deg.] C.

  The compounds of Example 342 and Example 343 were produced in the same manner as in Example 341, using the corresponding starting materials.

Example 342
4- [2- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-yl) ethyl] piperazine-1-carboxylic acid 4-trifluoromethylbenzyl ester slightly yellow Powder, yield 68%, mp 139-140 ° C.

Example 343
4- [3- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-yl) propyl] piperazine-1-carboxylic acid 4-trifluoromethylbenzyl ester slightly yellow Powder, yield 57%, mp 130-133 ° C.

Example 344
4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid 3- (4-trifluoromethylphenyl) -2-propynyl Preparation of ester maleate salt 2- (4-tert-butoxycarbonylpiperazin-1-yl) methyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] prepared in Example 306 A mixture of oxazole (220 mg, 0.6 mmol), trifluoroacetic acid (1 ml) and methylene chloride (2 ml) was stirred at room temperature for 2 hours. The reaction solution was concentrated under reduced pressure. The residue was dissolved in 2 ml of methylene chloride and neutralized by adding triethylamine (1 ml, 7.17 mmol). The resulting neutralized solution was concentrated under reduced pressure and the residue was dissolved in DMF (2 ml).

  While 3- (4-trifluoromethylphenyl) -2-propyn-1-ol (110 m, 0.55 mmol), 1,1'-carbonyldiimidazole (90 mg, 0.55 mmol) and DMF (2 ml) The mixture was stirred at room temperature for 2 hours to prepare an active ester.

  This active ester was added to the previous DMF solution and stirred overnight at room temperature. Water was added to the reaction solution and extracted twice with ethyl acetate. The organic phases were combined, washed twice with water, then washed with saturated brine, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride / ethyl acetate = 5/1).

The obtained free form was dissolved in 5 ml of ethanol, to which was added a solution of maleic acid (96 mg, 0.83 mmol) dissolved in ethanol (5 ml). The precipitated crystals are collected by filtration to give 4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid 3- (4-Trifluoromethylphenyl) -2-propynyl ester maleate (227 mg, yield 68%) was obtained.
Melting point 166 ° C (decomposition).

Example 345
Preparation of 4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid 4-methylsulfanyl benzyl ester Prepared as in Example 306 2- (4-tert-Butoxycarbonylpiperazin-1-yl) methyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole (900 mg, 2.4 mmol) and trifluoro A mixture of acetic acid (20 ml) was stirred at room temperature for 2 hours. The reaction solution was concentrated under reduced pressure. The residue was dissolved in 20 ml of methylene chloride and neutralized by adding triethylamine (6 ml, 43.05 mmol). Concentrated under reduced pressure. The residue was dissolved in DMF (5 ml).

  On the other hand, a mixture of 4-methylsulfanylbenzyl alcohol (470 mg, 3 mmol), 1,1'-carbonyldiimidazole (500 mg, 3.1 mmol) and DMF (10 ml) is stirred at room temperature for 3 hours to obtain an active ester. Was prepared.

This active ester was added to the previous DMF solution and stirred overnight at room temperature. Water was added to the reaction solution and extracted twice with ethyl acetate. The organic phases were combined, washed twice with water, then washed with saturated brine, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / methanol = 20/1) to give 4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole-2 as a white powder. -Ylmethyl) piperazine-1-carboxylic acid 4-methylsulfanyl benzyl ester (860 mg, 79% yield) was obtained.
Melting point 118-120 [deg.] C.

Example 346
Preparation of 4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid 4-methanesulfinyl benzyl ester Prepared as in Example 345 4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid 4-methylsulfanyl benzyl ester (300 mg, 0.67 mmol) To a mixture of methylene chloride and methylene chloride (10 ml), m-chloroperbenzoic acid (210 mg, 0.85 mmol) was added under ice-cooling, and the mixture was stirred at the same temperature for 2 hours. The reaction solution was washed successively with saturated aqueous sodium sulfite solution, saturated aqueous sodium bicarbonate solution and saturated brine, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue is recrystallized from isopropyl alcohol / ether and white powder of 4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid 4-methanesulfinyl benzyl ester (203 mg, 65% yield) was obtained.
Melting point 117-121 [deg.] C.

Example 347
Preparation of 4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid 4-hydroxybenzyl ester 4- (2-methyl-) 6-Nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carumnoate 4- (tert-butyldimethylsilanyloxy) benzyl ester (400 mg, 0.75 mmol) A solution of tetrabutylammonium fluoride (1 M) in THF (0.8 ml, 0.8 mmol) was added to a mixture of THF and THF (10 ml) under ice-cooling, and the mixture was stirred for 20 minutes at the same temperature. Ethyl acetate was added to the reaction mixture, and the mixture was washed successively with saturated aqueous ammonium chloride solution, water and saturated brine, dried over magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure. Diethyl ether is added to the residue, and the precipitated crystals are collected by filtration to obtain 4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) as a slightly yellow powder. Piperazine-1-carboxylic acid 4-hydroxybenzyl ester (95 mg, 30% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.59 (3H, s), 2.30-2.70 (4H, m), 2.56 (1H, d, J = 15.0 Hz), 2.86 (1 H, d, J = 15.0 Hz) ), 3.10-3.55 (4H, m), 3.91 (1 H, d, J = 10.0 Hz), 4.28 (1 H, d, J = 10.0 Hz), 5.03 (2 H) , S), 5.30 (1 H, brs), 6. 84 (2 H, d, J = 8.0 Hz), 7.24 (2 H, d, J = 8.0 Hz), 7.53 (1 H, s) ).

Example 348
Preparation of 4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid 4-acetylbenzyl ester 4- (2-methyl-) 6-Nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carnbonic acid 4- (1,1-dimethoxyethyl) benzyl ester (600 mg, 1.23 mmol), A mixture of 10 ml (10 mmol) of 1 N hydrochloric acid and THF (15 ml) was stirred at room temperature for 2 hours. The reaction mixture was neutralized by the addition of saturated aqueous sodium bicarbonate and extracted with ethyl acetate. After washing with water, it was washed with saturated brine, dried over magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure. Diethyl ether is added to the residue, and the precipitated crystals are collected by filtration to give 4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine as a white powder. The 1-carboxylic acid 4-acetylbenzyl ester (558 mg, 99% yield) was obtained.
101-102 ° C.

Example 349
Preparation of 4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid 4-benzoylbenzyl ester 4- (2-methyl-) 6-Nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carnbonic acid 4- (dimethoxy-phenylmethyl) benzyl ester (800 mg, 1.45 mmol) with 4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylate 4-benzoylbenzyl white powder according to the method of Example 348 The ester (630 mg, 86% yield) was obtained.
105-107 ° C.

Example 350
Preparation of 4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid 4-aminobenzyl ester 4- (2-methyl-) 6-Nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carnbonic acid 4- (tert-butoxycarbonylamino) benzyl ester (340 mg, 0.66 mmol), tri A mixture of 2 ml of fluoroacetic acid and methylene chloride (10 ml) was stirred at room temperature for 2 hours. Saturated aqueous sodium bicarbonate solution was added to the reaction solution for neutralization, and after separation, the reaction solution was washed successively with water and saturated brine, dried over magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure. Diethyl ether is added to the residue, and the precipitated crystals are collected by filtration to obtain 4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) as a slightly yellow powder. Piperazine-1-carboxylic acid 4-aminobenzyl ester (100 mg, 37% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.61 (3H, s), 2.35-2.70 (4H, m), 2.56 (1H, d, J = 15.0 Hz), 2.85 (1 H, d, J = 15.0 Hz) ), 3.05 to 3.55 (4H, m), 3.69 (2H, brs), 3.91 (1H, d, J = 10.0 Hz), 4.28 (1 H, d, J = 10) .0 Hz), 4.98 (2 H, s), 6.55 (2 H, d, J = 8, 0 Hz), 7.14 (2 H, d, J = 8.0 Hz), 7.53 (1 H, s) ).

Example 351
Preparation of 4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid phenylamide hydrochloride Prepared according to example 306 2- (4-tert-Butoxycarbonylpiperazin-1-yl) methyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole (130 mg, 0.35 mmol) and trifluoroacetic acid ( The mixture of 3 ml) was stirred overnight at room temperature. The reaction solution was concentrated under reduced pressure, the residue was dissolved in 3 ml of methylene chloride, and triethylamine (2 ml, 14.35 mmol) was added. To this solution was added phenylisocyanate (63 mg, 0.53 mmol) and stirred at room temperature for 30 minutes. Water was added to the reaction solution, extracted with methylene chloride, dried over magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride / methanol = 50/1) to give an amorphous.

The amorphous is dissolved in ethyl acetate, and crystals obtained by adding a saturated hydrochloric acid / ethyl acetate solution are collected by filtration to obtain 4- (2-methyl-6-nitro-2,3-dihydroimidazo [ 2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid phenylamide hydrochloride (124 mg, 55% yield) was obtained.
¹ H-NMR (DMSO-d ₆ ) δ ppm:
1.55 (3 H, s), 2.50-2.56 (4 H, m), 2. 75 (2 H, s), 3.21-3. 40 (4 H, m), 4.05 (1 H, 1 H, d, J = 10.7 Hz), 4.24 (1 H, d, J = 10.7 Hz), 6.92-6.99 (1 H, m), 7.21-7. 28 (2 H, m), 7.44-7.48 (2H, m), 8.13 (1 H, s), 8.59 (1 H, s).

Example 352
Preparation of 4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid isopropylamide 4- (2) prepared in Example 306 -Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid tert-butyl ester (140 mg, 0.38 mmol) and trifluoroacetic acid (3 ml) The mixture of) was stirred overnight at room temperature. The reaction solution was concentrated under reduced pressure, the residue was dissolved in 3 ml of methylene chloride, and triethylamine (2 ml, 14.35 mmol) was added. Isopropyl isocyanate (75 μl, 0.76 mmol) was added to this solution and stirred at room temperature for 1 hour. Water was added to the reaction solution, extracted with methylene chloride, dried over magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / methanol = 50/1) to give 4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole-2 as a white powder. -Ylmethyl) piperazine-1-carboxylic acid isopropylamide (90 mg, 67% yield) was obtained.
Melting point 175-176.3 ° C.

  The compounds of Example 353 and Example 354 were produced in the same manner as in Example 352, using the corresponding starting materials.

Example 353
4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid (3-chlorophenyl) amide
¹ H-NMR (DMSO-d ₆ ) δ ppm:
1.56 (3 H, s), 2.50-2.56 (4 H, m), 2.77 (2 H, s), 3.21-3. 40 (4 H, m), 4.08 (1 H, 1 H, d, J = 10.7 Hz), 4.26 (1 H, d, J = 10.7 Hz), 6.95 (1 H, bd, J = 8.0 Hz), 7.23 (1 H, t, J = 8 .0 Hz), 7.36 (1 H, bd, J = 8.0 Hz), 7.61 (1 H, t, J = 2.0 Hz), 8.13 (1 H, s), 8.61 (1 H, s) ).

Example 354
4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid cyclohexylamide melting point 216.5-218.5 ° C.

Example 355
Preparation of 4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carbothioic acid (4-chlorophenyl) amide Prepared as in Example 322 2-methyl-6-nitro-2- (piperazin-1-ylmethyl) -2,3-dihydroimidazo [2,1-b] oxazole dihydrochloride (196 mg, 0.73 mmol) is suspended in 10 ml of methylene chloride It became turbid and triethylamine (0.27 ml, 1.94 mmol) was added and homogenized. To this was added 4-chlorophenylisothiocyanate (140 mg, 0.83 mmol) and stirred at room temperature for 1 hour. The reaction solution was washed with water, then with saturated aqueous sodium bicarbonate solution and then with saturated brine, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / methanol = 30/1) to give 4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole- 2-ylmethyl) piperazine-1-carbothioic acid (4-chlorophenyl) amide (128 mg, 40% yield) was obtained.
Melting point 204-206 [deg.] C (decomposition).

  The compounds of Example 356 and Example 357 were produced in the same manner as in Example 355, using the corresponding starting materials.

Example 356
4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carbothioic acid phenylamide mp 164-165 ° C. (decomp.).

Example 357
4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carbothioic acid (4-methoxyphenyl) amide melting point 189-191 ° C (decomposition ).

Example 358
Preparation of 2- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] benzoxazole 2 prepared in Example 306 -(4-tert-Butoxycarbonylpiperazin-1-yl) methyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole (500 mg, 1.36 mmol) with trifluoroacetic acid It was dissolved in (10 ml) and stirred at room temperature for 3 hours. The reaction solution was concentrated under reduced pressure, and 1 ml each of methylene chloride and triethylamine were added. It was then stirred at room temperature for 5 minutes and then concentrated under reduced pressure. The residue was dissolved in methylene chloride, 2-chlorobenzoxazole (0.19 ml 1.63 mmol) and triethylamine (0.23 ml, 1.63 mmol) were added and stirred at room temperature for 1 hour. The reaction solution was poured into water and extracted with methylene chloride. The extract was washed with saturated brine, dried over magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / methanol = 100/1), and crystallization is performed from methylene chloride-diisopropyl ether to give 2- [4- (2-methyl-6-nitro-2, white powder] 3-Dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] benzoxazole (325 mg, yield 62%) was obtained.
MS 384 (M ⁺ )
Melting point 228.0-229.5 ° C.

  The compounds of Example 359 to Example 361 were produced in the same manner as in Example 358, using the corresponding starting materials.

Example 359
2- [4- (6-Nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] benzoxazole white powder, yield 74%
MS 370 (M ⁺ )
Melting point 206-209 [deg.] C (decomposition).

Example 360
2- {4- [2- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-yl) ethyl] piperazin-1-yl} benzoxazole white powder, 73% rate
MS 398 (M ⁺ )
Melting point 187.6-189.6 ° C.

Example 361
2- {4- [3- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-yl) propyl] piperazin-1-yl} benzoxazole white powder, 90% rate
MS 412 (M ⁺ )
Mp 172.0-174.4 ° C.

Example 362
Preparation of (S) -4- [3- (2-Chloro-4-nitroimidazol-1-yl) -2-hydroxypropyl] piperazine-1-carboxylic acid tert-butyl ester Prepared in Example 8 (R) 2-Chloro-1- [2-hydroxy-3- (4-methylbenzenesulfonyloxy) propyl] -4-nitroimidazole (16.86 g, 44.86 mmol) and piperazine-1-carboxylic acid tert-butyl ester (8.36 g, 44.89 mmol) was dissolved in acetonitrile (100 ml), to which triethylamine (6.3 ml, 45.2 mmol) was added and heated to reflux for 6 hours. The reaction solution was returned to room temperature and concentrated under reduced pressure. To the residue was added water (100 ml) and extracted twice with ethyl acetate (100 ml). The organic phases were combined, washed successively with water (100 ml) and saturated brine (100 ml), dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride / methanol = 40/1). Recrystallization from ethyl acetate / n-hexane to give (S) -4- [3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxypropyl] piperazine-1-carboxylic acid as pale yellow powdery crystals Acid tert-butyl ester (11.61 g, 66% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.46 (9 H, s), 2.21-2. 50 (4 H, m), 2.54-2. 70 (2 H, m), 3.39-3.48 (4 H, m), 3. 65 (1 H, s), 3.89-4. 10 (2 H, m), 4. 20 (1 H, dd, J = 1.9 Hz, 13.5 Hz), 8.00 (1 H, s).

Example 363
Preparation of (S) -4- [3- (2-Chloro-4-nitroimidazol-1-yl) -2-hydroxypropyl] piperazine-1-carboxylic acid tert-butyl ester (Separate synthesis of the compound of Example 362 Law)
(R) -2-Chloro-1- (2-oxiranylmethyl) -4-nitroimidazole (1 g, 4.91 mmol) prepared in Example 9, piperazine-1-carboxylic acid tert-butyl ester (1 A mixture of .01 g, 5.40 mmol) and DMF (3 ml) was stirred at 70 ° C. for 6 hours. The reaction solution is cooled to room temperature, 7 ml of water is added, and the precipitated crystals are collected by filtration. This was purified by silica gel column chromatography (methylene chloride / methanol = 40/1) to obtain (S) -4- [3- (2-chloro-4-nitroimidazol-1-yl)-of slightly yellow powdery crystals. 2-Hydroxypropyl] piperazine-1-carboxylic acid tert-butyl ester (967 mg, 51%) was obtained.

Example 364
Preparation of (R) -4- [3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxypropyl] piperazine-1-carboxylic acid tert-butyl ester 2-chloro-4-nitro-1H -Imidazole (6.1 g, 41.35 mmol), (S)-(+)-glycidyl tosylate (12.27 g, 53.75 mmol) and sodium hydrogen carbonate (7.3 g, 86.89 mmol) The mixture in ethanol (30 ml) was heated to reflux for 9 hours. The reaction solution was returned to room temperature, water was added, and the mixture was extracted twice with methylene chloride. The extract solution was washed with brine, dried over magnesium sulfate and filtered. The filtrate was concentrated and the resulting foam was dissolved in DMF (60 ml). In this solution, piperazine-1-carboxylic acid tert-butyl ester (8.47 g, 45.48 mmol), triethylamine (6.92 m, 49.64 mmol) and sodium iodide (6.82 g, 45.5 mmol) Was added and stirred at room temperature for 24 hours. The reaction was poured into water and extracted twice with ethyl acetate. The organic phases were combined, washed three times with water, dried over magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure, and the obtained residue is purified by silica gel column chromatography (ethyl acetate) to give (R) -4- [3- (2-chloro-4-nitroimidazole-) as a slightly yellow oil. 1-yl) -2-hydroxypropyl] piperazine-1-carboxylic acid tert-butyl ester (6.43 g, 40% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.48 (9 H, s), 2.16-2.50 (4 H, m), 2.55-2.69 (2 H, m), 3.37-3. 50 (4 H, m), 3. 65 (1 H, s), 3.90-4. 25 (3 H, m), 8.00 (1 H, s).

Example 365
Preparation of (S) -4- [3- (2-Chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] piperazine-1-carboxylic acid tert-butyl ester Preparation in Example 12 (R) -2-chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitroimidazole (7.00 g, 32.2 mmol) and piperazine-1-carboxylic acid tert-butyl ester ( A mixture of 6.29 g, 33.8 mmol) in DMF (70 ml) was stirred at 70 ° C. for 8 hours. The reaction solution was cooled to room temperature, water was added, and the mixture was extracted twice with ethyl acetate. The organic phases were combined, washed three times with water, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. To the residue was added diethyl ether, and the resulting crystals were collected by filtration. By drying under reduced pressure at room temperature, (S) -4- [3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] piperazine-1 of pale yellow powdery crystals is obtained. -Carboxylic acid tert-butyl ester (10.25 g, yield 79%) was obtained.
Optical purity> 98.4% ee
[Α] _D ²⁷ = 25.488 (concentration: 1.024, CHCl ₃ )
¹ H-NMR (CDCl ₃ ) δ ppm:
1.14 (3 H, s), 1.46 (9 H, s), 2. 34 (1 H, d, J = 13.9 Hz), 2.47-2.67 (5 H, m), 3.26 ( 1 H, s), 3.44 (4 H, t, J = 4.4 Hz), 3.99 (2 H, s), 8.04 (1 H, s).

Example 366
Preparation of (S) -4- [3- (2-Chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] piperazine-1-carboxylic acid tert-butyl ester (Example 365) Alternative synthesis of compounds)
2-Chloro-4-nitro-1H-imidazole (89.4, 606 mmol) and (S) -4- (2-methyloxiranylmethyl) piperazine-1-carboxylic acid tert-butyl ester (119 g, 466 mmol) The solution was dissolved in ethanol (475 ml), sodium hydrogen carbonate (58.7 g, 699 mmol) was added and the mixture was heated to reflux for 6 hours. The reaction mixture was concentrated under reduced pressure and extracted with ethyl acetate. The extract solution was dried over sodium sulfate and filtered. The crystals obtained by concentrating the filtrate under reduced pressure were dispersed and washed with ethyl acetate, and then collected by filtration to obtain primary crystals. The mother liquor was concentrated, and the residue was purified by silica gel column chromatography (n-hexane / acetone = 3/1) to obtain secondary crystals. The primary crystals and the secondary crystals are combined and dried under reduced pressure, and (S) -4- [3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] as white powder crystals. Piperazine-1-carboxylic acid tert-butyl ester (84.7 g, 45% yield) was obtained.

Example 367
Preparation of (R) -4- [3- (2-Chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] piperazine-1-carboxylic acid tert-butyl ester Preparation in Example 18 (S) -2-chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitroimidazole (440 mg, 2.02 mmol), piperazine-1-carboxylic acid tert-butyl ester (414 mg, A mixture of 2.22 mmol) and DMF (4 ml) was stirred at 55-60 ° C. for 9 hours. The reaction solution was returned to room temperature, water (24 ml) was added, and the mixture was extracted twice with ethyl acetate (10 ml). The organic phases were combined, washed three times with water (20 ml), washed with saturated brine (10 ml), dried over sodium sulfate and filtered. The filtrate is concentrated under reduced pressure, the residue is treated with diethyl ether, and the crystals obtained are collected by filtration to give (R) -4- [3- (2-chloro-4-nitroimidazol-1-yl)-of slightly yellow powdery crystals. 2-hydroxy-2-methylpropyl] piperazine-1-carboxylic acid tert-butyl ester (662 mg, yield 81%) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.15 (3 H, s), 1. 45 (9 H, s), 2. 34 (1 H, d, J = 13.9 Hz), 2.48-2.67 (5 H, m), 3.27 ( 1 H, s), 3.44 (4 H, t, J = 4.4 Hz), 3.99 (2 H, s), 8.04 (1 H, s).

  Analogously to Example 366 using 2-chloro-4-nitro-1H-imidazole and (R) -4- (2-methyl-2-oxiranylmethyl) piperazine-1-carboxylic acid tert-butyl ester The compound of Example 368 was produced.

Example 368
(R) -4- [3- (2-Chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] piperazine-1-carboxylic acid tert-butyl ester (compound of Example 367 Separate synthesis method)
White powdery crystals, 20% yield.

Example 369
(S) -1- (2-Chloro-4-nitroimidazol-1-yl) -2-methyl-3- [4- (4-trifluoromethoxyphenyl) piperazin-1-yl] propan-2-ol Preparation (S) -1- (2-Methyl-2-oxiranylmethyl) -4- (4-trifluoromethoxyphenyl) piperazine (0.43 g, 1.37 mmol) and 2-chloro-4-nitro- Sodium hydrogen carbonate (0.17 g, 2.06 mmol) was added to a suspension of 1H-imidazole (0.22 g, 1.51 mmol) in acetonitrile (4 ml) and heated to reflux for 9 hours. To the reaction solution was added water, extracted with ethyl acetate, dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (n-hexane / ethyl acetate = 3/1) to give (S) -1- (2-chloro-4-nitroimidazol-1-yl) -2- as a slightly yellow oil. Methyl 3- [4- (4-trifluoromethoxyphenyl) piperazin-1-yl] propan-2-ol (0.20 g, 31% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.18 (3 H, s), 2.41 (1 H, d, J = 13.8 Hz), 2.56 (1 H, d, J = 13.8 Hz), 2.67-2.80 (2 H, m) ), 2.85-2.96 (2H, m), 3.13-3.25 (4H, m), 4.03 (2H, s), 6.83-6. 93 (2H, m), 7.07-7.17 (2H, m), 8.07 (1 H, s).

Example 370
Preparation of (S) -1- (2-Chloro-4-nitroimidazol-1-yl) -2-methyl-3- [4- (4-chlorophenyl) piperazin-1-yl] propan-2-ol (R) -2-chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitroimidazole (20 g, 91.9 mmol) and 1- (4-chlorophenyl) piperazine prepared in 12 .8 g (0.11 mol) was added to DMF (200 ml) and stirred at 70-75.degree. C. for 5 hours. The reaction solution was returned to room temperature, poured into water and extracted with ethyl acetate. The extract was washed with saturated brine, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 20/1) to give yellow amorphous (S) -1- (2-chloro-4-nitroimidazol-1-yl) -2-methyl-3 There was obtained-[4- (4-chlorophenyl) piperazin-1-yl] propan-2-ol (33.0 g, yield 87%).
¹ H-NMR (CDCl ₃ ) δ ppm:
1.53 (3 H, s), 2.42 (1 H, d, J = 13.9 Hz), 2.55 (1 H, d, J = 13.9 Hz), 2.67-2.76 (2 H, m) ), 2.81 to 2.90 (2H, m), 3.13 to 3.17 (4H, m), 3.43 (1H, s), 4.03 (2H, s), 6.78- 6.85 (2H, m), 7.16 to 7.23 (2H, m), 8.06 (1 H, s).

  The compounds of Example 371 to Example 384 shown in the following table were produced in the same manner as in Example 370 using the corresponding starting materials.

  The compounds of Example 385 and Example 386 were produced in the same manner as in Example 370, using the corresponding starting materials.

Example 385
(S) -1- (2-Chloro-4-nitroimidazol-1-yl) -2-methyl-3- [4- (4-pyridyl) piperazin-1-yl] propan-2-ol 100% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
1.18 (3H, s), 2.44 (1H, d, J = 13.9 Hz), 2.56 (1 H, d, J = 13.9 Hz), 2.63-2.73 (2H, m) ), 2.77-2.91 (2H, m), 3.31-3.35 (4H, m), 3.54 (1H, s), 4.03-4.12 (2H, m), 6.63-6.66 (2H, m), 8.09 (1H, s), 8.23-8.27 (2H, m).

Example 386
(S) -1- (2-chloro-4-nitroimidazol-1-yl) -2-methyl-3- [4- (3-pyridyl) piperazin-1-yl] propan-2-ol yield 81%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.17 (3H, s), 2.44 (1 H, d, J = 13.9 Hz), 2.57 (1 H, d, J = 13.9 Hz), 2.67-2.79 (2 H, m) ), 2.84-2.93 (2H, m), 3.20-3.25 (4H, m), 3.85 (1H, bs), 4.06 (2H, s), 7.16. 7.19 (2H, m), 8.07-8.11 (2H, m), 8.26-8. 28 (1 H, m).

  The compounds of Example 387 to Example 389 were prepared in the same manner as in Example 370 using (R) -2-chloro-4-nitro-1- (2-oxiranylmethyl) imidazole prepared in Example 9. Manufactured.

Example 387
(S) -1- (2-chloro-4-nitroimidazol-1-yl) -3- [4- (4-fluorophenyl) piperazin-1-yl] propan-2-ol yield 86%
¹ H-NMR (CDCl ₃ ) δ ppm:
2.27-2.36 (1H, m), 2.49-2.63 (3H, m), 2.78-2.88 (2H, m), 2.97-3. 18 (4H, m) ), 3.74 (1H, br), 3.96 to 4.08 (2H, m), 4.18 to 4.24 (1H, m), 6.84 to 7.01 (4H, m), 8.02 (1 H, s).

Example 388
(S) -1- (2-Chloro-4-nitroimidazol-1-yl) -3- [4- (4-trifluoromethylphenyl) piperazin-1-yl] propan-2-ol yield 49%
¹ H-NMR (CDCl ₃ ) δ ppm:
2.27-2.36 (1H, m), 2.49-2.63 (3H, m), 2.78-2.87 (2H, m), 3.28-3. 31 (4H, m) ), 3.62 (1 H, br), 3.95-4. 11 (2 H, m), 4. 19-4. 25 (1 H, m), 6. 92 (2 H, d, J = 8.6 Hz) ), 7.49 (2H, d, J = 8.6 Hz), 8.02 (1 H, s).

Example 389
(S) -1- (2-Chloro-4-nitroimidazol-1-yl) -3- [4- (4-cyanophenyl) piperazin-1-yl] propan-2-ol 100% yield
¹ H-NMR (CDCl ₃ ) δ ppm:
2.28-2.37 (1H, m), 2.49-2.63 (3H, m), 2.76-2.85 (2H, m), 3.28-3. 36 (4H, m) ), 3.58 (1 H, br), 3.96 to 4.12 (2 H, m), 4. 19-4. 25 (1 H, m), 6. 87 (2 H, d, J = 8.9 Hz) ), 7.51 (2H, d, J = 8.9 Hz), 8.01 (1 H, s).

Example 390
Preparation of (S) -4- [3- (2-Chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] piperazine-1-carboxylic acid 4-trifluoromethoxybenzyl ester Example (R) -2-Chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitroimidazole (15 g, 68.93 mmol) prepared in 12 and piperazine-1-carboxylic acid 4-trifluoro The methoxybenzyl ester (25.17 g, 82.72 mmol) was stirred in 75 ml DMF at 65-70 ° C. for 20 hours. The reaction solution was returned to room temperature, poured into 150 ml of ethyl acetate and 475 ml of water, and separated. The aqueous layer was further extracted with 150 ml of ethyl acetate. The organic phases were combined, washed three times with 400 ml of water, then washed with 100 ml of saturated brine, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (ethyl acetate / n-hexane = 1/2) to give (S) -4- [3- (2-chloro-4-nitroimidazol-1-yl)-as a yellow oil. 2-hydroxy-2-methylpropyl] piperazine-1-carboxylic acid 4-trifluoromethoxybenzyl ester (29.98 g, 83% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.15 (3 H, s), 2.36 (1 H, d, J = 14.0 Hz), 2.42-2.75 (5 H, m), 3.18 (1 H, s), 3.42- 3.58 (4H, m), 4.00 (2H, s), 5.12 (2H, s), 7.21 (2H, d, J = 8.6 Hz), 7.38 (2H, d, J = 8.6 Hz), 8.03 (1 H, s).

Example 391
(S) -4- [3- (2-Chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] piperazine-1-carboxylic acid 3- (4-trifluoromethylphenyl)- Preparation of 2-propenyl ester (R) -2-Chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitroimidazole prepared in Example 12 (4.24 g, 19.48 mmol) and Piperazine-1-carboxylic acid 3- (4-trifluoromethylphenyl) -2-propenyl ester (6.73 g, 21.41 mmol) was stirred at 50-55 ° C. for 24 hours in 21 ml DMF. The reaction solution was returned to room temperature, poured into 60 ml of ethyl acetate and 90 ml of water, and separated. The aqueous layer was further extracted with 60 ml of ethyl acetate. The organic phases were combined, washed three times with 90 ml of water, then with 60 ml of saturated brine, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (ethyl acetate / n-hexane = 1/1) to give (S) -4- [3- (2-chloro-4-nitroimidazol-1-yl)-as a yellow oil. 2-hydroxy-2-methylpropyl] piperazine-1-carboxylic acid 3- (4-trifluoromethylphenyl) -2-propenyl ester (9.29 g, 90% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.16 (3 H, s), 2.36 (1 H, d, J = 14.0 Hz), 2.43-2.76 (5 H, m), 3.17 (1 H, s), 3.48- 3.67 (4H, m), 4.00 (2H, s), 4.78 (2H, dd, J = 1.0 Hz, 6.1 Hz), 6.33 to 6.48 (1 H, m), 6.66 (1 H, d, J = 15.9 Hz), 7.48 (2 H, d, J = 8.3 Hz), 7.58 (2 H, d, J = 8.3 Hz), 8.04 (1 H , S).

  The compound of Example 392 was produced in the same manner as in Example 391 using the corresponding starting materials.

Example 392
(S) -4- [3- (2-Chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] piperazine-1-carboxylic acid 3- (4-trifluoromethoxyphenyl)- 2-propenyl ester
¹ H-NMR (CDCl ₃ ) δ ppm:
1.15 (3 H, s), 2.36 (1 H, d, J = 13.9 Hz), 2.51 (1 H, d, J = 13.9 Hz), 2.48-2.63 (2 H, m ), 2.63 to 2.78 (2H, m), 3.17 (1H, s), 3.39 to 3.63 (4H, m), 4.00 (2H, s), 4.75 (4) 2H, dd, J = 1.1 Hz, 6.3 Hz), 6.28 (1 H, dt, J = 6.3 Hz, 15.9 Hz), 6.62 (1 H, d, J = 15.9 Hz), 7 15-15.18 (2H, m), 7.38-7. 42 (2H, m), 8.03 (1 H, s).

Example 393
Preparation of (S) -4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid tert-butyl ester Example 365 (S) -4- [3- (2-Chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] piperazine-1-carboxylic acid tert-butyl ester (10.25 g, 25.4 mmol) was dissolved in DMF (30 ml), sodium hydride (1.12 g, 27.9 mmol) was added under ice-cooling, and the mixture was stirred for 2 hours under the same temperature. Ethyl acetate (10 ml) and water (70 ml) were added to the reaction solution, and the precipitated crystals were collected by filtration and washed with water. The crude crystals were recrystallized from ethyl acetate (70 ml) to give (S) -4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole- of slightly yellow powdery crystals. 2-ylmethyl) piperazine-1-carboxylic acid tert-butyl ester (6.62 g, 71% yield) was obtained.
Optical purity> 99.5% ee
[Α] _D ²⁷ = −20.953 ° (concentration: 0.492, CHCl ₃ )
¹ H-NMR (CDCl ₃ ) δ ppm:
1.44 (9 H, s), 1.62 (3 H, s), 2.45-2. 66 (5 H, m), 2.87 (1 H, d, J = 14.9 Hz), 3.29 ( 4H, br), 3.92 (1 H, d, J = 9.7 Hz), 4.30 (1 H, d, J = 9.7 Hz), 7.53 (1 H, s).

Example 394
Preparation of (S) -4- (6-Nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid tert-butyl ester Prepared as in Example 363 (S Example) using)) 4- [3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxypropyl] piperazine-1-carboxylic acid tert-butyl ester (11 g, 28.22 mmol) By a method similar to 393, (S) -4- (6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid tert- of slightly yellow powdery crystals is obtained. The butyl ester (7.5 g, 75% yield) was obtained.
Optical purity 96.6% ee
[Α] _D ²² = -11.91 ° (concentration: 1.016, CHCl ₃ )
¹ H-NMR (CDCl ₃ ) δ ppm:
1.45 (9 H, s), 2.49-2.59 (4 H, m), 2. 85 (2 H, d, J = 5.2 Hz), 3.33-3.44 (4 H, m), 4.19 (1H, dd, J = 6.9 Hz, 10.2 Hz), 4.35 (1 H, dd, J = 6.9 Hz, 10.2 Hz), 5.36-5.49 (1 H, m) , 7.55 (1 H, s).

Example 395
Preparation of (R) -4- (6-Nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid tert-butyl ester Prepared as in Example 364 (R ), 4- [3- (2-Chloro-4-nitroimidazol-1-yl) -2-hydroxypropyl] piperazine-1-carboxylic acid tert-butyl ester (6.43 g, 16.49 mmol), 1, 1 The product was dissolved in 35 ml of 4-dioxane, sodium hydride (730 mg, 18.25 mmol) was added under ice-cooling, and the mixture was stirred overnight at room temperature and then heated under reflux for 24 hours. The reaction solution was returned to room temperature and concentrated under reduced pressure. The residue was slowly added with water, extracted twice with methylene chloride, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (ethyl acetate) to give (R) -4- (6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1 as a white powder. -Carboxylic acid tert-butyl ester (1.23 g, 21% yield) was obtained.
Optical purity> 99% ee
[Α] _D ²⁷ = 11.635 ° (concentration: 1.004, CHCl ₃ )
¹ H-NMR (CDCl ₃ ) δ ppm:
1.45 (9 H, s), 2.50-2.61 (4 H, m), 2. 85 (2 H, d, J = 5.3 Hz), 3.31-3. 50 (4 H, m), 4.18 (1H, dd, J = 6.9 Hz, 10.2 Hz), 4.35 (1 H, dd, J = 8.4 Hz, 10.2 Hz), 5.35-5.50 (1 H, m) , 7.55 (1 H, s).

Example 396
Preparation of (R) -4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid tert-butyl ester Example 368 The prepared (R) -4- [3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] piperazine-1-carboxylic acid tert-butyl ester (376 mg, 0. 1). 93 mmol) was dissolved in 1,4-dioxane (10 ml), sodium hydride (45 mg, 1.12 mmol) was added under ice-cooling, and the mixture was stirred at room temperature for 30 minutes and then heated under reflux for 24 hours. The reaction solution was returned to room temperature and concentrated under reduced pressure. To the residue was slowly added water, extracted twice with ethyl acetate, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (n-hexane / acetone = 3/1) and colorless powder crystals of (R) -4- (2-methyl-6-nitro-2,3-dihydroimidazo [2, 1 -B] Oxazol-2-ylmethyl) piperazine-1-carboxylic acid tert-butyl ester (239 mg, 70% yield) was obtained.
Optical purity 99.2% ee
[Α] _D ²⁷ = 21.073 ° (concentration: 0.522, CHCl ₃ )
¹ H-NMR (CDCl ₃ ) δ ppm:
1.45 (9H, s), 1.61 (3H, s), 2.45-2.64 (5H, m), 2.87 (1H, d, J = 14.9 Hz), 3.29 ( 4H, br), 3.92 (1 H, d, J = 9.7 Hz), 4.33 (1 H, d, J = 9.7 Hz), 7.52 (1 H, s).

Example 397
Preparation of (S) -2- [4- (4-Trifluoromethoxyphenyl) piperazin-1-ylmethyl] -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole Example (S) -1- (2-Chloro-4-nitroimidazol-1-yl) -2-methyl-3- [4- (4-trifluoromethoxyphenyl) piperazin-1-yl] propane-prepared in 369 Under ice-cooling, sodium hydride (0.66 g, 18.92 mmol) was added to a solution of 2-ol (5.85 g, 12.61 mmol) in THF (150 ml), and the mixture was heated under reflux for 6 hours. The reaction solution is concentrated under reduced pressure, ice-cooled, water and ethyl acetate are added, the precipitate is collected by filtration, purified by silica gel column chromatography (n-hexane / ethyl acetate = 1/1) and recrystallized from isopropanol Slightly yellow solid (S) -2- [4- (4-trifluoromethoxyphenyl) piperazin-1-yl] methyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b ] Oxazole (2.58 g, 48% yield) was obtained.
Optical purity 99.8% ee
[Α] _D ²⁶ = 8.80 ° (concentration: 1.000, CHCl ₃ )
Melting point 129-130 [deg.] C.

Example 398
Preparation of (S) -2- [4- (4-Chlorophenyl) piperazin-1-ylmethyl] -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole Prepared as in Example 370 (S) -1- (2-chloro-4-nitroimidazol-1-yl) -2-methyl-3- [4- (4-chlorophenyl) piperazin-1-yl] propan-2-ol (33. 0 g (79.7 mmol) was dissolved in DMF (300 ml). To this solution was added sodium hydride (3.7 g, 91.6 mmol) under ice-cooling, and the mixture was stirred overnight at room temperature. Ice water and ethyl acetate were added to the reaction solution and vigorously stirred. The precipitate was collected by filtration, washed with water and ethyl acetate, and dried under reduced pressure to obtain 23.2 g of a pale yellow powdery crude product. This is combined with the crude product (50 g) which was similarly synthesized once more, and purified by silica gel column chromatography (methylene chloride / ethyl acetate = 50/1), and crystallization is carried out from methylene chloride-ethyl acetate to obtain a white powder (S) -2- [4- (4-chlorophenyl) piperazin-1-ylmethyl] -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole (45 g, yield 90% Got).
Optical purity 99.6% ee
[Α] _D ²² = -10.20 ° (concentration: 0.5, CHCl ₃ )
Melting point 218-219.6 [deg.] C.

  The compounds of Example 399 to Example 403 were produced in the same manner as in Example 398, using the corresponding starting materials.

Example 399
(S) -2- [4- (4-fluorophenyl) piperazin-1-ylmethyl] -6-nitro-2,3-dihydroimidazo [2,1-b] oxazole yield 42%, [α] _D ²⁸ = 2.10 ° (concentration: 0.5, CHCl ₃ )
Mp 178.5-179.5 ° C.

Example 400
(S) -2- [4- (3-Pyridyl) piperazin-1-ylmethyl] -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole yield 42%, melting point 145 -147.7 ° C.

Example 401
(S) -2- [4- (4-Pyridyl) piperazin-1-ylmethyl] -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole yield 3%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.65 (3 H, s), 2.62 (1 H, d, J = 14.8 Hz), 2.64-2.71 (2 H, m), 2.79-2.89 (2 H, m), 2.92 (1 H, d, J = 14.8 Hz), 3.15-3.30 (4 H, m), 3.95 (1 H, d, J = 9.7 Hz), 4.33 (1 H, d , J = 9.7 Hz),
6.60 (2H, d, J = 6.2 Hz), 7.53 (1 H, s), 8.26 (2 H, d, J = 6.2 Hz).

Example 402
(S) -2- [4- (4-trifluoromethylphenyl) piperazin-1-ylmethyl] -6-nitro-2,3-dihydroimidazo [2,1-b] oxazole melting point 175.8-176.6 ° C.

Working Example 403
(S) -2- [4- (4-Cyanophenyl) piperazin-1-ylmethyl] -6-nitro-2,3-dihydroimidazo [2,1-b] oxazole mp 211-211.5 ° C.

Example 404
Preparation of (S) -2- [4- (4-chlorophenyl) piperazin-1-ylmethyl] -6-nitro-2,3-dihydroimidazo [2,1-b] oxazole 1- (4-chlorophenyl) piperazine. The dihydrochloride (1.31 g, 4.86 mmol) was poured into aqueous caustic soda and extracted with methylene chloride. The extract was dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to give 1- (4-chlorophenyl) piperazine.

Then 1- (4-chlorophenyl) piperazine obtained above and (R) -2-chloro-1- (2-oxiranylmethyl) -4-nitroimidazole prepared in Example 9 (763 mg; 75 mmol) were stirred in DMF (5 ml) at 70 ° C. for 6 hours. The reaction solution was ice-cooled, sodium hydride (219 mg, 5.48 mmol) was added, and the mixture was stirred at room temperature for 2 hours. Ice water was added to the reaction solution, and the precipitated crystals were collected by filtration. This is recrystallized from acetone / water to give (S) -2- [4- (4-chlorophenyl) piperazin-1-ylmethyl] -6-nitro-2,3-dihydroimidazo [2] as pale yellow powdery crystals. , 1-b] oxazole (250 mg, 18% yield) was obtained.
Melting point 183-183.5 ° C.

Example 405
Preparation of (S) -4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid 4-trifluoromethoxybenzyl ester 4-trifluoromethoxybenzyl (S) -4- [3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] piperazine-1-carboxylic acid prepared in Example 390 The ester (4.3 g, 8.24 mmol) was dissolved in DMF (13 ml) and cooled to 4 ° C. To this solution was added sodium hydride (430 mg, 10.7 mmol) and stirred at the same temperature for 2 hours. Ethyl acetate (4.3 ml) and water (30 ml) were sequentially added to the reaction solution, and the mixture was stirred for 30 minutes. The precipitated crystals were collected by filtration and washed with water. This is recrystallized from ethyl acetate / isopropyl ether and further recrystallized from isopropyl alcohol to give (S) -4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,2] as white powder crystals. 1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid 4-trifluoromethoxybenzyl ester (3.15 g, yield 79%) was obtained.
Melting point 139.5-140.5 ° C
Optical purity> 99.5% ee
[Α] _D ²⁷ = 18.04 ° (concentration: 1.020, CHCl ₃ )
¹ H-NMR (CDCl ₃ ) δ ppm:
1.60 (3 H, s), 2.39-2.75 (5 H, m), 2.87 (1 H, d, J = 14.9 Hz), 3.14-3.56 (4 H, m), 3.93 (1 H, d, 9.7 Hz), 4.29 (1 H, d, J = 9.7 Hz), 5. 10 (2 H, s), 7.19 (2 H, d, J = 8.6 Hz ), 7.36 (2H, d, J = 8.6 Hz), 7.54 (1 H, s).

Example 406
(S) -4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid 3- (4-trifluoromethylphenyl) Preparation of 2-Propenyl Ester (S) -4- [3- (2-Chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] piperazine-1-one prepared in Example 391 Carboxylic acid 3- (4-trifluoromethylphenyl) -2-propenyl allyl ester (13.2 g, 24.81 mmol) was dissolved in DMF (40 ml) and cooled to 4 ° C. Sodium hydride (1.19 g, 29.78 mmol) was added and stirred at the same temperature for 1.5 hours. Ethyl acetate (13 ml) and water (92 ml) were sequentially added to the reaction solution, and the mixture was stirred for 30 minutes. The precipitated crystals were collected by filtration and washed with water. The product is purified by silica gel column chromatography (ethyl acetate) to give (S) -4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole-2 as a slightly yellow powdery crystal. -Ylmethyl) piperazine-1-carboxylic acid 3- (4-trifluoromethylphenyl) -2-propenyl ester (10.17 g, yield 83%) was obtained.
132-133 ° C melting point
Optical purity 99.0% ee
[Α] _D ²⁷ = −21.73 ° (concentration: 0.866, CHCl ₃ )
¹ H-NMR (CDCl ₃ ) δ ppm:
1.62 (3H, s), 2.48-2.75 (5H, m), 2.88 (1H, d, J = 14.9 Hz), 3.15-3.57 (4H, m), 3.94 (1H, d, J = 9.7 Hz), 4.29 (1 H, d, J = 9.7 Hz), 4.75 (2 H, d, J = 1.15 Hz, 6.0 Hz), 6 .29-6.42 (1 H, m), 6.64 (1 H, d, J = 15.9 Hz), 7.47 (2 H, d, J = 8.4 Hz), 7.52-7. 3H, m).

  The compound of Example 407 was produced in the same manner as Example 406, using the corresponding starting materials.

Example 407
(S) -4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid 3- (4-trifluoromethoxyphenyl) -2-propenyl ester melting point 91-93 ° C
[Α] _D ²⁷ = −21.88 ° (concentration: 0.786, CHCl ₃ )
¹ H-NMR (CDCl ₃ ) δ ppm:
1.54 (3 H, s), 2, 38-2.71 (5 H, m), 2. 84 (1 H, d, J = 14.9 Hz), 3.13-3.54 (4 H, m), 3.92 (1 H, d, J = 9.7 Hz), 4. 29 (1 H, d, J = 9.7 Hz), 4.73 (2 H, dd, J = 1.2 Hz, 6.2 Hz), 6 .15-6.33 (1 H, m), 6.60 (1 H, d, J = 16.0 Hz), 7.16 (2 H, d, J = 8.7 Hz), 7.40 (2 H, d, J) J = 8.7 Hz), 7.53 (1 H, s).

Example 408
Preparation of (S) -2-Methyl-6-nitro-2- (piperazin-1-ylmethyl) -2,3-dihydroimidazo [2,1-b] oxazole dihydrochloride Prepared as in Example 393 (S ) -4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid tert-butyl ester (1.46 g, 3.98 The mmol) was dissolved in 30 ml of trifluoroacetic acid and stirred at room temperature for 3 hours. The reaction solution was concentrated under reduced pressure, the residue was dissolved in 30 ml of methanol, and a saturated hydrogen chloride-ethyl acetate solution was gradually added under ice-cooling, and the mixture was stirred for 30 minutes at the same temperature. The precipitated crystals are collected by filtration, and (S) -2-methyl-6-nitro-2- (piperazin-1-ylmethyl) -2,3-dihydroimidazo [2,1-b] oxazole dihydrochloride as yellow powder (994 mg, 73% yield) was obtained.
¹ H-NMR (DMSO-d ₆ ) δ ppm:
1.63 (3H, s), 2.80-3.36 (6H, m), 4.11 (1 H, d, J = 11.0 Hz), 4.25-4.98 (5 H, m), 8.15 (1 H, s), 9.31 (2 H, br).

Example 409
Preparation of (S) -6-Nitro-2- [4- (4-trifluoromethylbenzyl) piperazin-1-ylmethyl] -2,3-dihydroimidazo [2,1-b] oxazole Prepared as in Example 394 (S) -4- (6-Nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid tert-butyl ester (100 mg, 0.27 mmol) and tri The mixture of fluoroacetic acid (2 ml) was stirred at room temperature for 3 hours. The reaction solution was concentrated under reduced pressure, the residue was dissolved in 5 ml of methylene chloride, and triethylamine (1 ml, 7.17 mmol) was added to neutralize. The neutralized solution is concentrated under reduced pressure, the residue is dissolved in 5 ml of methanol, 4-trifluoromethylbenzaldehyde (148 mg, 0.85 mmol), sodium cyanoborohydride (53 mg, 0.85 mmol), acetic acid The solution was sequentially added (49 μl, 0.85 mmol) and stirred at room temperature for 18 hours. The reaction solution was concentrated under reduced pressure, saturated aqueous sodium bicarbonate was added to the residue, and the mixture was extracted twice with methylene chloride. The organic phases were combined, washed successively with saturated aqueous sodium bicarbonate solution and saturated brine, dried over magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 1/1) to obtain (S) -6-nitro-2- [4- (4) of pale yellow powdery crystals. -Trifluoromethylbenzyl) piperazin-1-ylmethyl] -2,3-dihydroimidazo [2,1-b] oxazole (53 mg, 46% yield) was obtained.
Melting point 149-150 [deg.] C.

Example 410
Preparation of (S) -2- [4- (4-biphenylylmethyl) piperazin-1-ylmethyl] -6-nitro-2,3-dihydroimidazo [2,1-b] oxazole Prepared as in Example 394 ( S) -4- (6-Nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid tert-butyl ester (7.2 g, 20.26 mmol), A mixture of 24 ml of trifluoroacetic acid and methylene chloride (72 ml) was stirred at room temperature for 2 hours. The reaction solution was concentrated under reduced pressure, the residue was dissolved in 100 ml of methylene chloride, and triethylamine (20 ml, 143.49 mmol) was added to neutralize. The neutralized solution is concentrated under reduced pressure, the residue is dissolved in 72 ml of methanol, 4-phenylbenzaldehyde (7.38 g, 40.52 mmol), sodium cyanoborohydride (3.82 g, 60.78 mmol) Acetic acid (3.48 ml, 60.78 mmol) was sequentially added and stirred at room temperature for 24 hours. The precipitated crystals were collected by filtration and washed with methanol. The resultant is purified by silica gel column chromatography (methylene chloride / methanol = 10/1) to obtain (S) -2- [4- (4-biphenylylmethyl) piperazin-1-ylmethyl] -6-nitro as yellow powdery crystals. There was obtained -2,3-dihydroimidazo [2,1-b] oxazole (5.52 g, yield 65%).
Optical purity> 99.0% ee
[Α] _D ²⁸ = −28.261 ° (concentration: 0.046, DMSO)
Melting point 207-208 [deg.] C.

Example 411
Preparation of (R) -2- [4- (4-biphenylylmethyl) piperazin-1-ylmethyl] -6-nitro-2,3-dihydroimidazo [2,1-b] oxazole Prepared as in Example 395 ( R) -4- (6-Nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid tert-butyl ester (101.5 mg, 0.29 mmol) and The mixture of trifluoroacetic acid (2 ml) was stirred at room temperature for 3 hours. The reaction solution was concentrated under reduced pressure, the residue was dissolved in 5 ml of methylene chloride, and triethylamine (2 ml, 14.35 mmol) was added to neutralize. The neutralized solution is concentrated under reduced pressure, the residue is dissolved in 5 ml of methanol, 4-phenylbenzaldehyde (156 mg, 0.86 mmol), sodium cyanotrihydroborate (53 mg, 0.84 mmol), acetic acid (0%) .05 ml, 0.87 mmol) in that order and stirred overnight at room temperature. The reaction solution was concentrated under reduced pressure, saturated aqueous sodium bicarbonate was added to the residue, and the mixture was extracted twice with methylene chloride. The organic phases were combined, washed successively with saturated aqueous sodium bicarbonate solution and saturated brine, dried over magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (ethyl acetate) to give (R) -2- [4- (4-biphenylylmethyl) piperazin-1-ylmethyl]-in the form of white powdery crystals. 6-nitro-2,3-dihydroimidazo [2,1-b] oxazole (56 mg, 46% yield) was obtained.
[Α] _D ²⁸ = 28.261 ° (concentration: 0.046, DMSO).
Melting point 224-225 ° C
The compound of Example 412 is produced in the same manner as Example 411 using the corresponding starting materials.

Example 412
(R) -6-Nitro-2- [4- (4-trifluoromethylbenzyl) piperazin-1-ylmethyl] -2,3-dihydroimidazo [2,1-b] oxazole yield 48%, melting point 141- 143 ° C.

Example 413
(S) -2-Methyl-6-nitro-2- [4- (4'-trifluoromethylbiphenyl-4-ylmethyl) piperazin-1-ylmethyl] -2,3-dihydroimidazo [2,1-b] Preparation of Oxazole (S) -4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid tert prepared as in Example 393 A mixture of -butyl ester (1.7 g, 4.6 mmol), trifluoroacetic acid (10 ml) and methylene chloride (30 ml) was stirred at room temperature for 3 hours. The reaction solution is concentrated under reduced pressure, the residue is dissolved in 30 ml of methanol, 4′-trifluoromethylbiphenyl-4-carbaldehyde (2.3 g, 9.19 mmol), sodium cyanotrihydroborate (580 mg, 9.23 mmol) and acetic acid (0.55 ml, 9.62 mmol) were sequentially added, and the mixture was stirred overnight at room temperature. The reaction solution was concentrated under reduced pressure, saturated aqueous sodium bicarbonate was added to the residue, and the mixture was extracted twice with methylene chloride. The organic phases were combined, washed successively with saturated aqueous sodium bicarbonate solution and saturated brine, dried over magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (methylene chloride / methanol = 50/1) to give (S) -2-methyl-6-nitro-2- [4-] as white powder crystals. (4'-Trifluoromethylbiphenyl-4-ylmethyl) piperazin-1-ylmethyl] -2,3-dihydroimidazo [2,1-b] oxazole (1.47 g, 63% yield) was obtained.
[Α] _D ²⁸ = 1.831 ° (concentration: 0.71, CHCl ₃ )
¹ H-NMR (CDCl ₃ ) δ ppm:
1.60 (3H, s), 2.20-2.45 (4H, m), 2.45-2.65 (4H, m), 2.50 (1 H, d, J = 15.0 Hz), 2.86 (1H, d, J = 15.0 Hz), 3.48 (2H, s), 3.89 (1 H, d, J = 10.0 Hz), 4.31 (1 H, d, J = 10 .0 Hz), 7.37 (2 H, d, J = 8.0 Hz), 7.50-7.56 (3 H, m), 7.68 (4 H, s).

  The compounds of Example 414 to Example 417 were produced in the same manner as in Example 413, using the corresponding starting materials.

Example 414
(S) -2-Methyl-6-nitro-2- [4- (4-trifluoromethylbenzyl) piperazin-1-ylmethyl] -2,3-dihydroimidazo [2,1-b] oxazole melting point 110-112 ° C.

Example 415
(S) -2- [4- (4-biphenylylmethyl) piperazin-1-ylmethyl] -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole melting point 182-184 ° C .

Example 416
(S) -2-Methyl-6-nitro-2- [4- (4-trifluoromethoxybenzyl) piperazin-1-ylmethyl] -2,3-dihydroimidazo [2,1-b] oxazole melting point 137-138 ° C.

Example 417
(S) -2- {4- [2- (4-chlorophenyl) -4-methylthiazol-5-ylmethyl] piperazin-1-ylmethyl} -2-methyl-6-nitro-2,3-dihydroimidazo [2] , 1-b] oxazole melting point 174.3-175.5 ° C.

Example 418
Preparation of (R) -2- [4- (4-biphenylylmethyl) piperazin-1-ylmethyl] -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole Example 396 (100 mg of (R) -4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid tert-butyl ester prepared in A mixture of 0.27 mmol) and trifluoroacetic acid (2 ml) was stirred at room temperature for 3 hours. The reaction solution was concentrated under reduced pressure, the residue was dissolved in 5 ml of methylene chloride, and triethylamine (1 ml, 7.17 mmol) was added to neutralize. The neutralized solution is concentrated under reduced pressure, the residue is dissolved in 5 ml of methanol, 4-phenylbenzaldehyde (149 mg, 0.82 mmol), sodium cyanotrihydroborate (51 mg, 0.82 mmol), acetic acid (48 μl) , 0.82 mmol) and stirred for 15 hours at room temperature. The reaction solution was concentrated under reduced pressure, and crystals obtained by adding saturated aqueous sodium bicarbonate to the residue were collected by filtration. The product is purified by silica gel column chromatography (ethyl acetate) to give (R) -2- (4-biphenyl-4-ylmethylpiperazin-1-ylmethyl) -2-methyl-6-nitro-2 as pale yellow powdery crystals. 3, 3-dihydroimidazo [2, 1-b] oxazole (67 mg, 57% yield) was obtained.
Melting point 112-114 [deg.] C.

  The compound of Example 419 was produced in the same manner as in Example 418, using the corresponding starting materials.

Example 419
(R) -2-Methyl-6-nitro-2- [4- (4-trifluoromethylbenzyl) piperazin-1-ylmethyl] -2,3-dihydroimidazo [2,1-b] oxazole melting point 93-95 ° C.

Example 420
Preparation of (S) -2-Chloro-1- [4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] ethanone (S) -4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid tert-butyl ester prepared in Example 393 A mixture of (1.5 g, 4.1 mmol) and 20 ml of trifluoroacetic acid was stirred at room temperature for 3 hours. The reaction solution was concentrated under reduced pressure. The residue is dissolved in 20 ml of methylene chloride and 3 ml of triethylamine, 4-dimethylaminopyridine (100 mg, 0.82 mmol) are added in order. Under ice-cooling, a solution of chloroacetyl chloride (0.49 ml, 6.2 mmol) dissolved in 2 ml of methylene chloride was slowly added dropwise, and the mixture was stirred overnight at room temperature. The reaction solution was washed twice with water, then sequentially washed with saturated aqueous sodium bicarbonate solution and saturated brine, dried over magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / methanol = 100/1) to obtain (S) -2-chloro-1- [4- (2-methyl-6-nitro-2,3-) of light tea powder. Dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] ethanone (600 mg, 43% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.64 (3 H, s), 2.50-2.70 (3 H, m), 2.61 (1 H, d, J = 15.0 Hz), 2.70-2.90 (1 H, m), 2.89 (1 H, d, J = 15.0 Hz), 3.15-3.55 (3 H, m), 3.60-3.75 (1 H, m), 3.97 (1 H, d, J = 10.0 Hz), 4.03 (2 H, s), 4. 30 (1 H, d, J = 10.0 Hz), 7.55 (1 H, s).

Example 421
(S) -2- (4-Chlorophenoxy) -1- [4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1 Preparation of [yl] ethanone (S) -2-Chloro-1- [4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole-2-one prepared in Example 420 Ylmethyl) piperazin-1-yl] ethanone (300 mg, 0.87 mmol), 4-chlorophenol (170 mg, 1.32 mmol), potassium carbonate (180 mg, 1.3 mmol) and a mixture of DMF (5 ml) Stir at <RTIgt; C </ RTI> for 3 hours. The reaction solution was cooled to room temperature, water was added, and the mixture was extracted twice with ethyl acetate. The organic phases were combined, washed successively with aqueous sodium hydroxide solution, water and saturated brine, dried over magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue is recrystallized from ethanol, and (S) -2- (4-chlorophenoxy) -1- [4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-] of pale tea powder. b] Oxazol-2-ylmethyl) piperazin-1-yl] ethanone (260 mg, 68% yield) was obtained.
Mp 179-180 ° C.

Example 422
(S) -2- (4-Chlorophenylsulfanyl) -1- [4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1 Preparation of [yl] ethanone (S) -2-Chloro-1- [4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole-2-one prepared in Example 420 (S)-in a similar manner to Example 421 using (Ilmethyl) piperazin-1-yl] ethanone (300 mg, 0.87 mmol) and 4-chlorothiophenol (190 mg, 1.32 mmol) 2- (4-Chlorophenylsulfanyl) -1- [4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazy -1-yl] ethanone (80 mg, 20% yield) was obtained.
Melting point 142-145 [deg.] C.

Example 423
Preparation of (S)-(4-Chlorophenyl)-[4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] methanone (S) -4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid tert-butyl ester prepared in Example 393 A mixture of (300 mg, 0.82 mmol) and trifluoroacetic acid (6 ml) was stirred at room temperature for 3 hours. The reaction solution was concentrated under reduced pressure. The residue was dissolved in 15 ml of methylene chloride and triethylamine (2 ml, 14.35 mmol) was added. Under ice cooling, 4-chlorobenzoyl chloride (150.7 mg, 0.86 mmol) was added, and the mixture was stirred at room temperature for 1 hour. The reaction solution was washed successively with saturated aqueous sodium bicarbonate solution, water and saturated brine, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue is treated with diethyl ether and ethyl acetate to give (S)-(4-chlorophenyl)-[4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] as yellow powdery crystals. Oxazol-2-ylmethyl) piperazin-1-yl] methanone (282 mg, yield 85%) was obtained.
Melting point 173-174 [deg.] C.

  The compound of Example 424 was produced in the same manner as in Example 423 using the corresponding starting materials.

Example 424
(4-Biphenylyl)-[4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] methanone melting point 116-118 [deg.] C.

Example 425
Preparation of [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] -phenylmethanone Prepared as in Example 306 -(4-tert-Butoxycarbonylpiperazin-1-yl) methyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole (142 mg, 0.39 mmol), trifluoroacetic acid A mixture of (1 ml) and methylene chloride (1 ml) was stirred at room temperature for 1 hour. The reaction solution was concentrated under reduced pressure. The residue was dissolved in 2 ml of methylene chloride and triethylamine (2 ml, 14.35 mmol) was added. Under ice-cooling, benzoyl chloride (54 μl, 0.46 mmol) was added, and the mixture was stirred at room temperature for 1 hour. The reaction solution was diluted with methylene chloride, washed successively with saturated aqueous sodium bicarbonate solution, water and saturated brine, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue is treated with diethyl ether and yellow powder crystals of [4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl]- Phenyl methanone (72 mg, 50% yield) was obtained.
Melting point 145-148.7 [deg.] C.

  The compounds of Example 426 to Example 433 were produced in the same manner as in Example 425, using the corresponding starting materials.

Example 426
(4-Chlorophenyl)-[4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] methanone melting point 150.0-155 .2 ° C.

Example 427
[4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl]-(pyridin-4-yl) methanone
¹ H-NMR (CDCl ₃ ) δ ppm:
1.62 (3H, s), 2.25-2.75 (4H, m), 2.61 (1H, d, J = 14.9 Hz), 2.88 (1 H, d, J = 14.9 Hz) ), 3.00 to 3.93 (4H, br), 3.95 (1H, d, J = 9.8 Hz), 4.30 (1 H, d, J = 9.8 Hz), 7.26 to 7 .55 (2H, m), 7.59 (1 H, s), 8.67-8.72 (2 H, m).

Example 428
1- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] -2-phenylethanone melting point 175.2- 175.9 ° C.

Example 429
1- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] -3-phenylpropan-1-one melting point 166 .8-169.1 ° C.

Example 430
1- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] -2-phenoxyethanone melting point 158-160.6 ° C.

Example 431
2- (4-Chlorophenyl) -1- [4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] ethanone melting point 184 -187 ° C.

Example 432
(4-Biphenylyl)-[4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] methanone
¹ H-NMR (CDCl ₃ ) δ ppm:
1.63 (3H, s), 2.45-2.80 (4H, m), 2.62 (1H, d, J = 14.9 Hz), 2.90 (1 H, d, J = 14.9 Hz) ), 3.28-3.81 (4H, br), 3.95 (1H, d, J = 9.8 Hz), 4.31 (1H, d, J = 9.8 Hz), 7.34-7. 50 (5 H, m), 7.55 (1 H, s), 7.56-7.63 (4 H, m).

Example 433
[4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl]-(4-trifluoromethylphenyl) methanone melting point 161- 162 ° C.

Example 434
(S)-[4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl]-(4-trifluoromethylphenyl) Preparation of Methanone (S) -2-Methyl-6-nitro-2- (piperazin-1-ylmethyl) -2,3-dihydroimidazo [2,1-b] oxazole dihydrochloride prepared in Example 408 2, 36 mg (0.882 mmol) was suspended in 10 ml of methylene chloride, and triethylamine (1 ml, 7.17 mmol) was added to give a homogeneous solution. To this solution was added 4- (trifluoromethyl) benzoyl chloride (193 mg, 0.926 mmol) under ice-cooling, and the mixture was stirred at room temperature for 1 hour. The reaction solution was washed successively with saturated aqueous sodium bicarbonate solution, water and saturated brine, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / methanol = 50/1) to give (S)-[4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1] as white powdery crystals. -B] oxazol-2-ylmethyl) piperazin-1-yl]-(4-trifluoromethylphenyl) methanone (264 mg, 68% yield) was obtained.
Melting point 183-184 [deg.] C.

  The compounds of Example 435 to Example 438 were produced in the same manner as in Example 434, using the corresponding starting materials. The compounds of Examples 435 to 437 can be prepared by the method described in Example 322 using the compound 2-methyl-6-nitro-2- (piperazin-1-ylmethyl) -2,3-dihydroimidazo [2,1-b] oxazole dihydrochloride prepared in Example 322. Made from salt.

Example 435
[4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl]-(4-methoxyphenyl) methanone mp 135-137 ° C .

Example 436
[4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl]-(4-methylphenyl) methanone melting point 121-122 ° C. .

Example 437
[4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl]-(3-trifluoromethylphenyl) methanone melting point 122- 124 ° C.

Example 438
(S) -2- (4 chlorophenyl) -1- [4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] Ethanone melting point 189-190 ° C.

Example 439
(S) -2- (3,4-Dichlorophenoxy) -1- [4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine- Preparation of 1-yl] ethanone A mixture of 3,4- (dichlorophenoxy) acetic acid (234 mg, 1.06 mmol) and thionyl chloride (5 ml) was heated to reflux for 30 minutes. The reaction was concentrated under reduced pressure to give the corresponding acid chloride.

On the other hand, (S) -2-Methyl-6-nitro-2- (piperazin-1-ylmethyl) -2,3-dihydroimidazo [2,1-b] oxazole dihydrochloride (236 mg) prepared in Example 408 , 0.88 mmol) was suspended in 10 ml of methylene chloride, and triethylamine (1 ml, 7.17 mmol) was added to give a solution. A solution of the above acid chloride dissolved in 5 ml of methylene chloride was gradually added thereto under ice cooling, and the mixture was stirred at room temperature for 1 hour. The reaction solution was washed successively with saturated aqueous sodium bicarbonate solution, water and saturated brine, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / methanol = 50/1) to give (S) -2- (3,4-dichlorophenoxy) -1- [4- (2-methyl-6) as white powder crystals. -Nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] ethanone (183 mg, yield 44%) was obtained.
Mp 164-166 ° C.

  The compound of Example 440 is produced in the same manner as in Example 439 using the corresponding starting materials.

Example 440
(S) -1- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] -4- (4-tri- Fluoromethylphenyl) butan-1-one mp 145-146 ° C.

Example 441
(S) -3- (4-chlorophenyl) -1- [4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl Preparation of propenone 4-chlorocinnamic acid (300 mg, 1.64 mmol), 1-hydroxybenzotriazole (HOBT) (240 mg, 1.77 mmol), WSCD (350 mg, 1.83 mmol) and methylene chloride (10 ml) The mixture was stirred at room temperature for 30 minutes to adjust the corresponding active ester.

Meanwhile, (S) -2-Methyl-6-nitro-2- (piperazin-1-ylmethyl) -2,3-dihydroimidazo [2,1-b] oxazole dihydrochloride (434 mg) prepared in Example 408 , 1.64 mmol) was suspended in 10 ml of methylene chloride, and triethylamine (3.3 ml, 2,37 mmol) was added and dissolved. The reaction liquid of said active ester was added there under ice-cooling, and it stirred under room temperature for 3 hours. The reaction solution was washed successively with saturated aqueous sodium bicarbonate solution, water and saturated brine, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (ethyl acetate) to give (S) -3- (4-chlorophenyl) -1- [4- (2-methyl-6-nitro-2,3-dihydroimidazo) as white powder crystals. [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] propenone (180 mg, 26% yield) was obtained.
Melting point 220-222 [deg.] C.

  The compounds of Examples 442 to 454 were produced in the same manner as in Example 441, using the corresponding starting materials.

Example 442
(S) -3- (Chlorophenyl) -1- [4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] propane -1-one melting point 177-178 ° C.

Example 443
(S) -4- (4-Chlorophenyl) -1- [4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl ] Butan-1-one melting point 146-147 ° C.

Example 444
(S) -3- (3,4-Dichlorophenyl) -1- [4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1 -Yl] propenone mp 213-215 ° C.

Example 445
(S) -5- (4-Chlorophenyl) -1- [4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl ] Pentan-1-one mp 108-111 ° C.

Example 446
Preparation of 1- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] -2- (4-tolyl) ethanone 2-Methyl-6-nitro-2- (piperazin-1-ylmethyl) -2,3-dihydroimidazo [2,1-b] oxazole dihydrochloride (240 mg, 0.79 mmol) prepared in Example 322 Was dissolved in 5 ml DMF and neutralized by adding triethylamine (0.22 ml, 1.58 mmol). Subsequently, p-tolylacetic acid (140 mg, 0.93 mmol) and WSCD (180 mg, 0.93 mmol) were sequentially added to the neutralized solution, and stirred at room temperature for 1 hour. The reaction solution is diluted with ethyl acetate, washed twice with water, then sequentially washed with saturated aqueous sodium bicarbonate solution and saturated brine, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue is treated with ether and white powder of 1- [4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl]- 2- (4-Tolyl) ethanone (172 mg, 64% yield) was obtained.
Melting point 213-214 [deg.] C.

  The compound of Example 447 was produced in the same manner as in Example 446, using the corresponding starting materials.

Example 447
(4-Dimethylaminophenyl)-[4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] methanone melting point 204-207 ° C.

Example 448
(S) -2- {4- [3- (4-chlorophenyl) propane-1-sulfonyl] piperazin-1-ylmethyl} -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b Preparation of Oxazole] (S) -4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid prepared in Example 393 A mixture of tert-butyl ester (300 mg, 0.82 mmol) and trifluoroacetic acid (10 ml) was stirred at room temperature for 1 hour. The reaction solution was concentrated under reduced pressure and the residue was dissolved in 10 ml of methylene chloride. Triethylamine (3 ml, 21.52 mmol) is added to this solution, and after stirring for 10 minutes at room temperature, 3- (4-chlorophenyl) propane-1-sulfonyl chloride (300 mg, 1.19 mmol) is added, and the solution is stirred at room temperature. And stirred for 3 days. The reaction solution is washed with water, then with saturated brine, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / methanol = 50/1) to give (S) -2- {4- [3- (4-chlorophenyl) propane-1-sulfonyl] piperazine-1-white powder. Ylmethyl} -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole (330 mg, 84% yield) was obtained.
Melting point 150-151 [deg.] C.

  Example 448 Using 2- (4-tert-butoxycarbonylpiperazin-1-ylmethyl) -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole prepared in Example 306 The compounds of Example 449 and Example 450 were produced in the same manner.

Example 449
2- [4- (4-Chlorobenzenesulfonyl) piperazin-1-ylmethyl] -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole melting point 202-204 ° C.

Example 450
2- [4- (4-Chlorophenylmethanesulfonyl) piperazin-1-ylmethyl] -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole mp 215-217 ° C.

Example 451
(S) -2- {4- [2- (4-chlorophenyl) ethanesulfonyl] piperazin-1-ylmethyl} -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole Preparation (S) -2-Methyl-6-nitro-2- (piperazin-1-ylmethyl) -2,3-dihydroimidazo [2,1-b] oxazole dihydrochloride (236 mg, prepared in Example 408) 0.88 mmol) was dissolved in 3 ml of DMF, potassium carbonate (500 mg, 3.62 mmol) and 2- (4-chlorophenyl) ethanesulfonyl chloride (240 mg, 1 mmol) were sequentially added, and the mixture was stirred overnight at room temperature. Water was added to the reaction solution and extracted with ethyl acetate. After washing with water three times, it was washed with saturated brine, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / methanol = 50/1) to give (S) -2- {4- [2- (4-chlorophenyl) ethanesulfonyl] piperazin-1-ylmethyl} as white powdery crystals. 2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole (100 mg, 26% yield) was obtained.
Melting point 192-193 [deg.] C.

  It is carried out using (S) -2-methyl-6-nitro-2- (piperazin-1-ylmethyl) -2,3-dihydroimidazo [2,1-b] oxazole dihydrochloride prepared in Example 408. The compounds of Example 452 to Example 454 were produced in the same manner as in Example 451. In addition, using 2-methyl-6-nitro-2- (piperazin-1-ylmethyl) -2,3-dihydroimidazo [2,1-b] oxazole dihydrochloride prepared in Example 322, Example 451 and The compound of Example 455 was produced in the same manner.

Example 452
(S) -2- [4- (4-Chlorobenzenesulfonyl) piperazin-1-ylmethyl] -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole mp 216-218 ° C.

Example 453
(S) -2- [4- (4-Chlorophenylmethanesulfonyl) piperazin-1-ylmethyl] -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole melting point 204-206 ° C.

Example 454
(S) -2- {4- [4- (4-chlorophenyl) butane-1-sulfonyl] piperazin-1-ylmethyl} -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b Mp 176-177 ° C.

Working Example 455
2- {4- [2- (4-chlorophenyl) ethanesulfonyl] piperazin-1-ylmethyl} -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole melting point 182-184 ° C .

Example 456
Preparation of (S) -4- (6-Nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid 4-trifluoromethylbenzyl ester Prepared in Example 394 (S) -4- (6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid tert-butyl ester (300 mg, 0.84 mmol) It was dissolved in 2 ml of methylene chloride, 1 ml of trifluoroacetic acid was added, and the mixture was stirred at room temperature for 1 hour. The reaction solution was concentrated under reduced pressure, the residue was dissolved in 1 ml of DMF, and 1 ml of triethylamine was added to neutralize.

  Meanwhile, 4- (trifluoromethyl) benzyl alcohol (297 mg, 1.69 mmol) is dissolved in 1 ml of DMF, 1,1'-carbonyldiimidazole (274 mg, 1.69 mmol) is added, and the reaction is continued for 1 hour at room temperature. Stir to prepare an active ester.

The solution of this active ester was added to the previous neutralization solution and stirred at room temperature for 3 hours. Water was added to the reaction solution and extracted twice with ethyl acetate. The organic phases were combined, washed twice with water, then washed with saturated brine, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / methanol = 20/1) to give (S) -4- (6-nitro-2,3-dihydroimidazo [2,1-b] oxazole- of white powdery crystals. 2-ylmethyl) piperazine-1-carboxylic acid 4-trifluoromethylbenzyl ester (273 mg, 71% yield) was obtained.
[Α] _D ²⁸ = −14.851 ° (concentration: 0.404, CHCl ₃ )
Melting point 125-125.5 [deg.] C.

Example 457
Preparation of (S) -4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid 4-trifluoromethylbenzyl ester (S) -4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid tert-butyl ester prepared in Example 393 1.87 g (5.09 mmol) was dissolved in methylene chloride (20 ml), trifluoroacetic acid (20 ml) was added, and the mixture was stirred for 5 minutes and concentrated under reduced pressure. The residue was dissolved in DMF (20 ml). To a solution of 4- (trifluoromethyl) benzyl alcohol (1.92 g, 10.9 mmol) in DMF (20 ml) was added 1,1'-carbonyldiimidazole (1.76 g, 10.9 mmol) for 3 hours at room temperature The stirred mixture was added and stirred at room temperature overnight. After extraction with ethyl acetate, the organic phases were combined and washed with water and brine. After drying over sodium sulfate, it was filtered. The resulting filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane / acetone = 3/1). By recrystallization from isopropyl alcohol, filtering and drying under reduced pressure, (S) -4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole of slightly yellow powdery crystals is obtained. 2-ylmethyl) piperazine-1-carboxylic acid 4-trifluoromethylbenzyl ester (1.48 g, 53% yield) was obtained.
Melting point 140.4-141.6 ° C
Optical purity 99.9% ee
¹ H-NMR (CDCl ₃ ) δ ppm:
1.62 (3 H, s), 2.52-2. 69 (5 H, m), 2.88 (1 H, d, J = 14.9 Hz), 3.43 (4 H, br), 3.93 (3) 1H, d, J = 9.7 Hz), 4.28 (1 H, d, J = 9.7 Hz), 5.16 (2 H, s), 7.44 (2 H, d, J = 8.1 Hz), 7.53 (1 H, s), 7.61 (2 H, d, J = 8.1 Hz).

Example 458
(S) -4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid 1,3,3-trimethyl-2- Preparation of oxo-2,3-dihydro-1H-indol-5-ylmethyl ester (S) -4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole-2 To a mixture of 3-ylmethyl) piperazine-1-carboxylic acid 3,3-dimethyl-2-oxo-2,3-dihydro-1H-indol-5-ylmethyl ester (300 mg, 0.62 mmol) and DMF (3 ml) Under ice-cooling, sodium hydride (27 mg, 0.68 mmol) was added and stirred at the same temperature for 30 minutes. Subsequently, methyl iodide (97 mg, 0.68 mmol) was added to the mixture and stirred at room temperature for 2 hours. Water was added to the reaction solution and extracted twice with ethyl acetate. The organic phases were combined, washed twice with water, then washed with saturated brine, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (ethyl acetate), and the pale yellow powder of (S) -4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole-2-one) Ylmethyl) piperazine-1-carboxylic acid 1,3,3-trimethyl-2-oxo-2,3-dihydro-1H-indol-5-ylmethyl ester (140 mg, 45%) was obtained.
Mp 80-100 ° C (decomposition).

  The compound of Example 459 was produced in the same manner as in Example 458, using the corresponding starting materials.

Example 459
(S) -4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid 1-methyl-2-oxo-1, 2,3,4-Tetrahydroquinolin-6-ylmethyl ester mp 189-190 ° C.

Example 460
Preparation of (S) -4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid 3,5-dichlorobenzyl ester (S) -2-Methyl-6-nitro-2- (piperazin-1-ylmethyl) -2,3-dihydroimidazo [2,1-b] oxazole dihydrochloride prepared in Example 408 (300 mg, 0.88 Triethylamine (270 mg, 2.67 mmol) was added to a mixture of mmol) and DMF (3 ml) to neutralize. Dissolve 3,5-dichlorobenzyl alcohol (180 mg, 1.02 mmol) in DMF (3 ml), add 1,1'-carbonyldiimidazole (180 mg, 1.11 mmol) and stir at room temperature for 2 hours The solution of active ester prepared above was added to the above-mentioned neutralization liquid, and it stirred under room temperature overnight. Water was added to the reaction solution, and extracted twice with ethyl acetate. The organic phases were combined, washed twice with water, washed with saturated brine, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (ethyl acetate) to give (S) -4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole-2-yl) as white powder crystals. Ylmethyl) piperazine-1-carboxylic acid 3,5-dichlorobenzyl ester (220 mg, 53% yield) was obtained.
Melting point 129-130 [deg.] C.

Working Example 461
(S) -4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid 3- (3-trifluoromethylphenyl) Preparation of 2-Propenyl Ester Maleate Salt (S) -4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl prepared in Example 393 ) (P) -l-carboxylic acid tert-butyl ester (1.09 g, 2.97 mmol) by the method of Example 344 to give (S) -4- (2-methyl-6-nitro-2) as a white powder 3, 3-Dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid 3- (3-trifluoromethylphenyl) -2-propenyl ester. A leinate (945 mg, 63%) was obtained.
Melting point 136-138 [deg.] C.

  The compounds of Example 462 to Example 465 were produced in the same manner as in Example 461 using the corresponding starting materials.

Example 462
(S) -4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid [(E) -3-methyl-3 -(3-Trifluoromethylphenyl)]-2-propenyl ester maleate melting point 142-143 [deg.] C.

Example 463
(S) -4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid 3- (3-chlorophenyl) -2- Propenyl ester maleate melting point 150-151 [deg.] C.

Example 464
(S) -4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid 3- (2,4,6-trichoric acid Fluorophenyl) -2-propenyl ester maleate melting point 158-159 [deg.] C.

Example 465
(S) -4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid [(Z) -3-methyl-3 -(3-Trifluoromethylphenyl)]-2-propenyl ester maleate mp 124-125 ° C.

Example 466
Preparation of (R) -4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid 4-fluorobenzyl ester Example 396 (R) -4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid tert-butyl ester (106 mg, 0.29 mmol) according to the method of Example 457 using (R) -4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole-2-) as a white powder. Ylmethyl) piperazine-1-carboxylic acid 4-fluorobenzyl ester (79 mg, 66% yield) was obtained.
[Α] _D ²⁸ = 19.70 ° (concentration: 1.066, CHCl ₃ )
Melting point 167-169 [deg.] C.

Example 467
(S) -4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid [3- (4-trifluoromethylphenyl) Preparation of) -2-propenyl] amide 3- (4-Trifluoromethylphenyl) -2-propenylamine (761 mg, 3.78 mmol), 1,1'-carbonyldiimidazole (613 mg, 3.78 mmol) and The mixture of DMF (3 ml) was stirred overnight at room temperature to be a reaction solution.

Meanwhile, (S) -4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid tert- produced in Example 393 A mixture of butyl ester (926 mg, 2.52 mmol), trifluoroacetic acid (10 ml) and methylene chloride (3 ml) was stirred at room temperature for 5 hours. The reaction solution was concentrated under reduced pressure, the residue was dissolved in 3 ml of DMF, and triethylamine (2 ml, 14.35 mmol) was added. The above reaction solution was added to this, and stirred overnight at room temperature. Water was added to the reaction solution and extracted with ethyl acetate. After washing with water three times, it was washed with saturated brine, dried over magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / methanol = 20/1) to give (S) -4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-] as a slightly yellow powder. b] Oxazol-2-ylmethyl) piperazine-1-carboxylic acid [3- (4-trifluoromethylphenyl) -2-propenyl] amide (1.2 g, yield 96%) was obtained.
105-107 ° C.

  Example using 2- (4-tert-butoxycarbonylpiperazin-1-yl) methyl-2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole prepared in Example 306 The compounds of Examples 468 to 470 were produced in the same manner as in 467.

Example 468
4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid (4-trifluoromethylbenzyl) amide melting point 201-202. 5 ° C.

Example 469
4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid (4-trifluoromethylphenyl) amide melting point 216-217 ° C .

Example 470
4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid (4-chloro-3-trifluoromethylphenyl) amide melting point 222-224 ° C.

Example 471
Preparation of (S) -4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid cyclohexylamide Prepared as in Example 408 Chlorinated (S) -2-methyl-6-nitro-2- (piperazin-1-ylmethyl) -2,3-dihydroimidazo [2,1-b] oxazole dihydrochloride (236 mg, 0,88 mmol) It was suspended in 15 ml of methylene and homogenized by adding triethylamine (2 ml, 14.35 mmol). To this was added cyclohexylisocyanate (120 mg, 0.96 mmol) and stirred at room temperature for 1 hour. The reaction solution is washed with water, then with saturated brine, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / methanol = 20/1) to give (S) -4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-] as a slightly yellow powder. b] Oxazol-2-ylmethyl) piperazine-1-carboxylic acid cyclohexylamide (164 mg, 47%) was obtained.
Melting point 98-101 ° C.

  As in Example 471, using 2-methyl-6-nitro-2- (piperazin-1-ylmethyl) -2,3-dihydroimidazo [2,1-b] oxazole dihydrochloride prepared in Example 322. The compounds of Examples 472-476 were prepared.

Example 472
4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid (4-methoxyphenyl) amide melting point 167-168 ° C.

Example 473
4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid (4-chlorophenyl) amide melting point 185-188 ° C (decomposition) .

Working Example 474
4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid (3-trifluoromethylphenyl) amide melting point 183-184 ° C .

Example 475
4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid (3,4-dichlorophenyl) amide melting point 212-214 ° C. Disassembly).

Example 476
4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid (4-methylphenyl) amide melting point 202-203 ° C (decomposition ).

Example 477
(S) -4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid (4-trifluoromethylphenyl) amide Preparation A mixture of 4-aminobenzotrifluoride (142 mg, 0,882 mmol), 1,1'-carbonyldiimidazole (143 mg, 0.882 mmol) and DMF (6 ml) was stirred overnight at room temperature to obtain a reaction solution. And

On the other hand, (S) -2-methyl-6-nitro-2- (piperazin-1-ylmethyl) -2,3-dihydroimidazo [2,1-b] oxazole dihydrochloride (236 mg, prepared in Example 408) 0.088 mmol) was suspended in 5 ml of methylene chloride and homogenized by adding triethylamine (2 ml, 14.35 mmol). The above DMF reaction solution was added to this, and stirred at room temperature for 6 hours. Water was added to the reaction solution and extracted with ethyl acetate. After washing with water three times, it was washed with saturated brine, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / methanol = 30/1) to give (S) -4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-] as white powder crystals. b] Oxazol-2-ylmethyl) piperazine-1-carboxylic acid (4-trifluoromethylphenyl) amide (90 mg, 23% yield) was obtained.
Melting point 150-152.5 [deg.] C.

  The compounds of Example 478 to Example 481 were produced in the same manner as in Example 477, using the corresponding starting materials.

Example 478
(S) -4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid (4-methoxyphenyl) amide melting point 185. 5-187.5 ° C.

Example 479
(S) -4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid (4-trifluoromethylbenzyl) amide melting point 101-103.6 ° C.

Example 480
(S) -4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid (4-chlorophenyl) amide melting point 156-159 ° C (decomposition).

Example 481
(S) -4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid (4-methylphenyl) amide melting point 207- 210 ° C. (decomposition).

Example 482
(S) -4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid N-methyl-N- (4-triethyl ester) Preparation of fluoromethylphenyl) amide (S) -4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1 prepared in Example 477 -Carboxylic acid (4-trifluoromethylphenyl) amide (200 mg, 0.44 mmol) is dissolved in 4 ml of DMF, sodium hydride (26 mg, 0.66 mmol) is added and after stirring for 1.5 hours at room temperature Methyl iodide (0.5 ml, 0.76 mmol) was added and stirred overnight at room temperature. Water was added to the reaction solution and extracted with ethyl acetate. After washing with water three times, it was washed with saturated brine, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / methanol = 50/1) to give (S) -4- (2-methyl-6-nitro-2, 3-dihydroimidazo [2, 1-1] as white powder crystals. b] Oxazol-2-ylmethyl) piperazine-1-carboxylic acid N-methyl-N- (4-trifluoromethylphenyl) amide (35 mg, 17% yield) was obtained.
Melting point 100.4-102.4.degree.

Example 483
(S)-[4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl]-[4- (4-trifluoro Preparation of methylphenyl) piperidin-1-yl] methanone (S) -4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole-2-one prepared in Example 393 A mixture of ylmethyl) piperazine-1-carboxylic acid tert-butyl ester (1.17 g, 3.32 mmol), trifluoroacetic acid (5 ml) and methylene chloride (10 ml) was stirred at room temperature for 2 hours. The reaction solution was concentrated under reduced pressure, the residue was dissolved in 10 ml of methylene chloride, triethylamine (5 ml, 35.87 mmol) was added, and the mixture was stirred at room temperature for 10 minutes. The solution is concentrated under reduced pressure, the residue is dissolved in 15 ml of DMF, potassium carbonate (920 mg, 6.64 mmol) is added, and 4- (4-trifluoromethylphenyl) piperidine-1-carbonyl chloride (1 A solution of .07 g (3.65 mmol) in 10 ml of DMF was slowly added dropwise. The mixture was stirred overnight at room temperature. Water was added to the reaction solution and extracted with ethyl acetate. After washing with water three times, it was washed with saturated brine, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / methanol = 30/1) to give (S)-[4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1] as white powder crystals. -B] oxazol-2-ylmethyl) piperazin-1-yl]-[4- (4-trifluoromethylphenyl) piperidin-1-yl] methanone (575 mg, 33% yield) was obtained.
Melting point 179.1-181.9 ° C.

Example 484
(S)-[4- (4-chlorophenyl) -1,2,3,6-tetrahydropyridin-1-yl]-[4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,2, Preparation of 1-b] oxazol-2-ylmethyl) piperazin-1-yl] methanone (S) -2-Methyl-6-nitro-2- (piperazin-1-ylmethyl) -2,3 prepared in Example 408 -Dissolve dihydroimidazo [2,1-b] oxazole dihydrochloride (401 mg, 1.5 mmol) in 8 ml DMF, add potassium carbonate (750 mg, 5.4 mmol) and stir for 10 minutes at room temperature A solution of 4- (4-chlorophenyl) -1,2,3,6-tetrahydropyridine-1-carbonyl chloride (400 mg, 1.56 mmol) in 3 ml of DMF was gradually added under ice cooling. It dripped. The mixture was stirred overnight at room temperature. Water was added to the reaction solution and extracted with ethyl acetate. After washing with water three times, it was washed with saturated brine, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue is recrystallized from ethanol to give (S)-[4- (4-chlorophenyl) -1,2,3,6-tetrahydropyridin-1-yl]-[4- (2-methyl-) as pale yellow powdery crystals. 6-Nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] methanone (380 mg, yield 53%) was obtained.
Mp 161-162 ° C.

  It is carried out using (S) -2-methyl-6-nitro-2- (piperazin-1-ylmethyl) -2,3-dihydroimidazo [2,1-b] oxazole dihydrochloride prepared in Example 408. The compounds of Example 485 and Example 486 were produced in the same manner as in Example 484. Alternatively, using the 2-methyl-6-nitro-2- (piperazin-1-ylmethyl) -2,3-dihydroimidazo [2,1-b] oxazole dihydrochloride prepared in Example 322, the procedure of The compound of Example 487 was produced in the same manner.

Example 485
(S)-[4- (4-chlorophenyl) piperidin-1-yl]-[4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) Piperazin-1-yl] methanone mp 156-159 ° C.

Example 486
(S)-[4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl]-[4- (4-trifluoro Methylphenyl) -1,2,3,6-tetrahydropyridin-1-yl] methanone mp 168.4-171.7 ° C.

Example 487
[4- (4-Chlorophenyl) piperidin-1-yl]-[4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1 [I] Methanone melting point 186-187 ° C.

Example 488
Preparation of (S) -4- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] benzoic acid (S) -4- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] benzoic acid tert-butyl ester (300 mg, 0 .68 mmol) were stirred in 10 ml of trifluoroacetic acid for 5 hours at room temperature. The reaction solution was concentrated under reduced pressure and neutralized with triethylamine. This is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (methylene chloride / methanol = 20/1), and crystallization is performed from methanol-diisopropyl ether to give (S) -4- [4- (white powder 2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] benzoic acid (186 mg, 71% yield) was obtained.
MS 387 (M ⁺ )
Melting point 248-252 [deg.] C.

Example 489
(S) -2- [4- (2,6-diphenylpyrimidin-4-yl) piperazin-1-ylmethyl] -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole Preparation of (S) -4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid tert- prepared according to example 393 The butyl ester (500 mg, 1.36 mmol) was dissolved in 2 ml of methylene chloride, 10 ml of trifluoroacetic acid was added and stirred at room temperature for 3 hours. The reaction solution was concentrated under reduced pressure, and 4 ml each of methylene chloride and triethylamine were added. The reaction solution was stirred at room temperature for 5 minutes and then concentrated under reduced pressure. The residue was dissolved in 5 ml of DMF, 4-chloro-2,6-diphenylpyrimidine (400 mg, 1.50 mmol), DBU (0.2 ml, 1.36 mmol) were added and stirred at 100 ° C. for 5 hours. The reaction solution was returned to room temperature, poured into water and extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / methanol = 100/1), crystallized from methylene chloride-diisopropyl ether, and white powder of (S) -2- [4- (2,6-diphenylpyrimidine -4-yl) piperazin-1-ylmethyl] -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole (113 mg, 17% yield) was obtained.
MS 498 (M + H) ⁺
Melting point 202.5-205.4 [deg.] C.

  The compound of Example 490 was produced in the same manner as in Example 489, using the corresponding starting materials.

Example 490
(S) -2- [4- (4,6-diphenylpyrimidin-2-yl) piperazin-1-ylmethyl] -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole Yield 7%, mp 201.2-205.4 ° C.

Example 491
Preparation of {4- [3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] piperazin-1-yl} carbamic acid tert-butyl ester 2-chloro-4- Nitro-1H-imidazole (2.05 g, 13.9 mmol), 4- (2-methyl-2-oxiranylmethyl) piperazin-1-yl) carbamic acid tert-butyl ester (3.14 g, 11.6) The mmol) and sodium hydrogen carbonate (1.46 g, 17.4 mmol) were heated and stirred in 13 ml of 1-propanol for 6 hours. The reaction solution was extracted twice with ethyl acetate, then the organic phases were combined and washed with saturated brine. After drying over sodium sulfate, it was filtered. The resulting filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (n-hexane / acetone = 2/1) to give {4- [3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy- of white powder crystal. 2-Methylpropyl] piperazin-1-yl} carbamic acid tert-butyl ester (1.55 g, 32% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.12 (3 H, s), 1.46 (9 H, s), 2.36 (1 H, d, J = 13.9 Hz), 2.50 (1 H, d, J = 13.9 Hz), 64- 2.84 (8 H, m), 3.32 (1 H, s), 3.96 (2 H, s), 5. 46 (1 H, br), 8.03 (1 H, s).

Example 492
Preparation of {4- [3- (2-Chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] piperazin-1-yl} carbamic acid tert-butyl ester (Compound of Example 491 Separately synthesized method of
2-chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitroimidazole (4.36 g, 20.0 mmol) prepared in Example 6 and piperazin-1-yl-carbamic acid tert- Using butyl ester (4.44 g, 22.0 mmol) and according to a method similar to Example 365, {4- [3- (2-chloro-4-nitroimidazol-1-yl) -2 as a white powder crystal -Hydroxy-2-methylpropyl] piperazin-1-yl} carbamic acid tert-butyl ester (6.08 g, 72% yield) was obtained.

Example 493
Preparation of [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] carbamic acid tert-butyl ester Preparation in Example 492 16. 4- (3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl) piperazin-1-yl} carbamic acid tert-butyl ester (6.87 g, 16.3. [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) in the form of white powdery crystals, using 4 mmol) and in the same manner as in Example 393. Piperazin-1-yl] carbamic acid tert-butyl ester (2.71 g, 43% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.43 (9 H, s), 1. 60 (3 H, s), 2. 36 (1 H, d, J = 14.0 Hz), 2.52-2.90 (9 H, m), 3.90 ( 1H, d, J = 9.7 Hz), 4.27 (1 H, d, J = 9.7 Hz), 5.35 (1 H, br), 7.53 (1 H, s).

Example 494
Preparation of [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] carbamic acid benzyl ester Prepared as in Example 493 4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] carbamic acid tert-butyl ester (150 mg, 0.39 mmol) And a mixture of trifluoroacetic acid (4 ml) was stirred at room temperature for 3 hours. The reaction solution was concentrated under reduced pressure. The residue was dissolved in 4 ml of methylene chloride and neutralized by addition of triethylamine (4 ml, 28.7 mmol). Then, to this was added benzyl chloroformate (100 mg, 0.59 mmol) under ice cooling, and the mixture was stirred at room temperature for 2 hours. Saturated aqueous sodium bicarbonate was added to the reaction solution, and the mixture was extracted with methylene chloride. After washing with water, it was washed with saturated brine, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (n-hexane / acetone = 1/1) to give [4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] as pale yellow powder crystal. ] Oxazol-2-ylmethyl) piperazin-1-yl] carbamic acid benzyl ester (6.5 mg, 4% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.60 (3 H, s), 2.53-2. 90 (10 H, m), 3.89 (1 H, d, J = 9.6 Hz), 4.27 (1 H, d, J = 9.6 Hz) ), 5.11 (2H, s), 5.88 (1 H, br), 7.25-7.34 (5 H, m), 7.52 (1 H, s).

Example 495
N- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] -N- (4-trifluoromethoxybenzylidene) Preparation of Amine) [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] carbamic acid prepared in Example 493 A mixture of 4-butyl ester (40 mg, 0.11 mmol), 4-trifluoromethoxybenzaldehyde (24 mg, 0.13 mmol), 0.08 ml of trifluoroacetic acid and methylene chloride (1 ml) was stirred at room temperature for 3 hours . The mixture was neutralized with saturated aqueous sodium bicarbonate solution and extracted with methylene chloride. After washing with water, it was washed with saturated brine, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 3/1) to give N- [4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-] as white powder crystals. b] Oxazol-2-ylmethyl) piperazin-1-yl] -N- (4-trifluoromethoxybenzylidene) amine (19 mg, 40% yield) was obtained.
Mp 189.2-190.9 ° C.

Example 496
(S) -1- (2-Chloro-4-nitroimidazol-1-yl) -2-methyl-3- {4-[(4-trifluoromethylbenzylidene) amino] piperazin-1-yl} propane-2 (R) -2-Chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitroimidazole prepared in Example 12 (218 mg, 1 mmol), N- (piperazine-1) A mixture of -yl) -N- (4-trifluoromethylbenzylidene) amine (283 mg, 1.1 mmol) and DMF (2 ml) was stirred at 70-80 C for 7 hours. The reaction solution was cooled to room temperature, water was added, and the mixture was extracted twice with ethyl acetate. The organic phases were combined, washed three times with water, then washed with saturated brine, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (n-hexane / acetone = 1/1) to obtain (S) -1- (2-chloro-4-nitroimidazol-1-yl) -2-methyl of pale yellow powdery crystals. -3- {4-[(4-Trifluoromethylbenzylidene) amino] piperazin-1-yl} propan-2-ol (402 mg, 85% yield) was obtained.
[Α] _D ²⁷ = 19.01 ° (concentration: 1.010, CHCl ₃ )
¹ H-NMR (CDCl ₃ ) δ ppm:
1.18 (3H, s), 2.42 (1H, d, J = 13.9 Hz), 2.57 (1 H, d, J = 13.9 Hz), 2.71-2.95 (4 H, m) , 3.10-3.33 (5 H, m), 4.02 (2 H, s), 7.51 (1 H, s), 7.58 (2 H, d, J = 8.4 Hz), 7. 68 (2H, d, J = 8.4 Hz), 8.05 (1 H, s).

Example 497
Preparation of (S)-{4- [3- (2-Chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] piperazin-1-yl} carbamic acid tert-butyl ester Example (R) -2-chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitroimidazole (29.8 g, 137 mmol) prepared in 12 and piperazin-1-yl-carbamic acid tert- Using butyl ester (28.9 g, 144 mmol) and according to a method similar to Example 496, (S)-{4- [3- (2-chloro-4-nitroimidazol-1-yl) as white powder crystals -2-Hydroxy-2-methylpropyl] piperazin-1-yl} carbamic acid tert-butyl ester (36.68 g, 64% yield) was obtained.
[Α] _D ²⁷ = 17.793 ° (concentration: 1.006, CHCl ₃ )
¹ H-NMR (CDCl ₃ ) δ ppm:
1.12 (3H, s), 1.45 (9H, s), 2.36 (1H, d, J = 14.0 Hz), 2.50 (1 H, d, J = 14.0 Hz), 64- 2.84 (8 H, m), 3.32 (1 H, s), 3.97 (2 H, s), 5. 47 (1 H, br), 8.04 (1 H, s).

  The compounds of Example 498 to Example 500 were produced in the same manner as in Example 497, using the corresponding starting materials.

Example 498
(S) -1- (2-Chloro-4-nitroimidazol-1-yl) -2-methyl-3- {4-[(4-trifluoromethoxybenzylidene) amino] piperazin-1-yl} propane-2 -All [α] _D ²⁷ = 12.326 ° (concentration: 1.006, CHCl ₃ )
¹ H-NMR (CDCl ₃ ) δ ppm:
1.17 (3H, s), 2.41 (1H, d, J = 13.9 Hz), 2.56 (1 H, d, J = 13.9 Hz), 2.71-2.95 (4 H, m) , 3.14-3.29 (5H, m), 4.01 (2H, s), 7.19 (2H, d, J = 8.0 Hz), 7.50 (1 H, s), 7.. 62 (2H, d, J = 8.0 Hz), 8.05 (1 H, s).

Working Example 499
(S) -1- (2-Chloro-4-nitroimidazol-1-yl) -2-methyl-3- {4-[(5-trifluoromethylbenzofuran-2-ylmethylene) amino] piperazin-1-yl } Propane-2-ol
¹ H-NMR (CDCl ₃ ) δ ppm:
1.18 (3 H, s), 2.43 (1 H, d, J = 14.0 Hz), 2.58 (1 H, d, J = 14.0 Hz), 2.73-2.82 (2 H, m) ), 2.86-2.95 (2H, m), 3.17 (1H, s), 3.31 (4H, s), 4.03 (2H, s), 6.82 (1 H, s) , 7.46 (1 H, s), 7.52 (1 H, d, J = 8.7 Hz), 7.59 (1 H, d, J = 8.7 Hz), 7.83 (1 H, s), 8 .05 (1 H, s).

Example 500
(S) -1- {4-[(5-chlorobenzofuran-2-ylmethylene) amino] piperazin-1-yl} -3- (2-chloro-4-nitroimidazol-1-yl) -2-methylpropane -2-all
¹ H-NMR (CDCl ₃ ) δ ppm:
1.18 (3 H, s), 2.42 (1 H, d, J = 14.0 Hz), 2.57 (1 H, d, J = 14.0 Hz), 2.71-3.00 (4 H, m) ), 3.17 (1 H, s), 3.23-3. 38 (4 H, m), 4.02 (2 H, s), 6.71 (1 H, s), 7.22 (1 H, dd, J = 2.1 Hz, 8.7 Hz), 7.33-7.43 (2 H, m), 7. 50 (1 H, d, J = 2.1 Hz), 8.05 (1 H, s).

Example 501
(S) -1- (2-Chloro-4-nitroimidazol-1-yl) -2-methyl-3- [4- (4-trifluoromethylphenylamino) piperazin-1-yl] propan-2-ol Preparation of (R) -2-Chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitroimidazole (0.610 g, 2.82 mmol) prepared in Example 12 and Piperazine-1 A colorless solid (S) -1- (2-chloro-4-nitro) was prepared by the same method as in Example 496 using ethyl- (4-trifluoromethylphenyl) amine (0.760 g, 3.09 mmol). Imidazol-1-yl) -2-methyl-3- [4- (4-trifluoromethylphenylamino) piperazin-1-yl] propan-2-ol (1.125 g, yield 86%) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.15 (3H, s), 2.39 (1H, d, J = 14.0 Hz), 2.54 (1 H, d, J = 14.0 Hz), 2.60-2.95 (8 H, m) ), 3.25 (1H, s), 3.99 (2H, s), 4.67 (1H, s), 6.90 (2H, d, J = 8.6 Hz), 7.43 (2H, 2H, s) d, J = 8.6 Hz), 8.04 (1 H, s).

Example 502
(S) -N- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl]-(4-trifluoromethyl) Preparation of Phenyl) amine (S) -1- (2-Chloro-4-nitroimidazol-1-yl) -2-methyl-3- [4- (4-trifluoromethylphenylamino) prepared in Example 501 A similar procedure to Example 493 using piperazin-1-yl] propan-2-ol (1.125 g, 2.43 mmol) gave (S)-[4- (2-methyl-6-) as a white solid. Nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl]-(4-trifluoromethylphenyl) amine (0.715 g, yield 69%) was obtained .
Melting point 192.1-195.3 ° C.

Example 503
Preparation of (S)-[4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] carbamic acid tert-butyl ester Tert-Butyl (S)-{4- [3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] piperazin-1-yl} carbamate prepared in Example 497 Using ester (36.68 g) and according to a method similar to Example 493, (S)-[4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] in the form of white powdery crystals. ]] Oxazol-2-ylmethyl) piperazin-1-yl] carbamic acid tert-butyl ester (19.51 g, yield 58%) was obtained.
Optical purity> 99.5% ee
[Α] _D ²⁷ = 9.84 ° (concentration: 1.016, CHCl ₃ )
¹ H-NMR (CDCl ₃ ) δ ppm:
1.43 (9 H, s), 1. 60 (3 H, s), 2. 35 (1 H, d, J = 14.0 Hz), 2.52-2.92 (9 H, m), 3.89 ( 1 H, d, J = 9.7 Hz), 4.27 (1 H, d, J = 9.7 Hz), 5.35 (1 H, s), 7.53 (1 H, s).

Working Example 504
(S) -N- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] -N- (4-tri) Preparation of Fluoromethylbenzylidene) amine (S) -1- (2-Chloro-4-nitroimidazol-1-yl) -2-methyl-3- {4-[(4-trifluoromethyl) prepared in Example 496 Sodium hydride (69 mg, 1.73 mmol) was added to a mixture of (benzylidene) amino] piperazin-1-yl} propan-2-ol (847 mg, 0.85 mmol) and DMF (4 ml) under ice-cooling, It stirred under the same temperature for 2.5 hours. Water was added to the reaction solution, and the precipitated crystals were collected by filtration. The crystals are washed with methanol and then recrystallized from acetone / water to give (S) -N- [4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1] as pale yellow powder crystals. -B] oxazol-2-ylmethyl) piperazin-1-yl] -N- (4-trifluoromethylbenzylidene) amine (248 mg, yield 69%) was obtained.
Melting point 201-202.3 ° C (decomposition)
Optical purity> 99.5% ee
[Α] _D ²⁷ = -64.64 ° (concentration: 1.018, CHCl ₃ )
¹ H-NMR (CDCl ₃ ) δ ppm:
1.64 (3H, s), 2.55-2.79 (3H, m), 2.80-3.20 (7H, m), 3.94 (1 H, d, J = 9.7 Hz), 4.33 (1 H, d, J = 9.7 Hz), 7.44 (1 H, s), 7.48-7.67 (5 H, m).

  The compounds of Example 505 to Example 507 were produced in the same manner as in Example 504, using the corresponding starting materials.

Example 505
(S) -N- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] -N- (4-tri) Fluoromethoxybenzylidene) amine melting point 188.4-191.2 ° C
Optical purity> 99.0% ee
[Α] _D ²⁷ = −58.30 ° (concentration: 1.024, CHCl ₃ )
¹ H-NMR (CDCl ₃ ) δ ppm:
1.64 (3 H, s), 2.55-2.77 (3 H, m), 2.82-3.18 (7 H, m), 3.94 (1 H, d, J = 9.7 Hz), 4.33 (1 H, d, J = 9.7 Hz), 7.16 (2 H, d, J = 8.2 Hz), 7.43 (1 H, s), 7.55 (1 H, s), 7. 58 (2H, d, J = 8.2 Hz).

Example 506
(S) -N- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] -N- (5-tri) Fluoromethylbenzofuran-2-ylmethylene) amine melting point 190.2-191.8 ° C
Optical purity 99.8% ee
[Α] _D ²⁷ = −81.05 ° (c = 0.992, CHCl ₃ )
¹ H-NMR (CDCl ₃ ) δ ppm:
1.64 (3 H, s), 2.59-2.77 (3 H, m), 2. 6- 3.0 (3 H, m), 3.05-3. 26 (4 H, m), 3. 96 (1 H, d, J = 9.7 Hz), 4.33 (1 H, d, J = 9.7 Hz), 6.79 (1 H, s), 7.39 (1 H, s), 7.41- 7.57 (3H, m), 7.82 (1 H, s).

Example 507
(S) -N- (5-chlorobenzofuran-2-ylmethylene) -N- [4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) Piperazin-1-yl] amine optical purity> 99.0% ee
[Α] _D ²⁷ = -84.48 ° (concentration: 1.018, CHCl ₃ )
Melting point 213.8-215.7 ° C
¹ H-NMR (CDCl ₃ ) δ ppm:
1.63 (3H, s), 2.57-2.76 (3H, m), 2.81-2.95 (3H, m), 3.00-3. 24 (4H, m), 3. 94 (1 H, d, J = 9.7 Hz), 4.32 (1 H, d, J = 9.7 Hz), 6.67 (1 H, s), 7.17-7.23 (1 H, m), 7.30-7.43 (2H, m), 7.48 (1 H, d, J = 2.1 Hz), 7.53 (s, 1 H).

Example 508
(S) -N- (5-chlorobenzofuran-2-ylmethylene) -N- [4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) Preparation of Piperazin-1-yl] amine (Another synthesis of the compound of Example 507)
(S)-[4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] carbamic acid tert prepared according to example 503 -Butyl ester (0.20 g, 0.523 mmol) and 5-chlorobenzofuran-2-carbaldehyde (0.113 g, 0.628 mmol) are dissolved in 4 ml of methylene chloride and 0.4 ml of trifluoroacetic acid is added, Stir at room temperature for 2 hours. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with methylene chloride. The organic phase was washed with brine. The organic phase was dried over sodium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride / ethyl acetate = 4/1). (S) -N- (5-Chlorobenzofuran-2-ylmethylene) -N- [4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole] of slightly yellow powdery crystals -2-ylmethyl) piperazin-1-yl] amine (0.137 g, 59% yield) was obtained.

Example 509
(S) -N- [1- (4-chlorophenyl) ethylidene] -N- [4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) Preparation of Piperazin-1-yl] amine (S)-[4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) prepared in Example 503 A mixture of piperazin-1-yl] carbamic acid tert-butyl ester (200 mg, 0.52 mmol), 2 ml of trifluoroacetic acid and methylene chloride (4 ml) was stirred at room temperature for 30 minutes. The reaction solution was concentrated under reduced pressure, the residue was dissolved in 4 ml of methylene chloride, and triethylamine (4 ml, 28.7 mmol) was added to neutralize. To the neutralized solution was added a solution of 4-chloroacetophenone (97 mg, 0.63 mmol) dissolved in 4 ml of ethanol, and heated under reflux for 4 hours. The reaction solution was returned to room temperature and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane / acetone = 3/1). (S) -N- [1- (4-Chlorophenyl) ethylidene] -N- [4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole in slightly yellow powdery crystals -2-ylmethyl) piperazin-1-yl] amine (39 mg, 18% yield) was obtained.
Mp 164.6-166.5 ° C.

  The compounds of Example 510 to Example 513 were produced in the same manner as in Example 509, using the corresponding starting materials.

Example 510
(S) -N- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] -N- [1- ( 4-trifluoromethylphenyl) ethylidene] amine melting point 167.9-169.4 ° C.

Example 511
(S) -N- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] -N- [1- ( 4-trifluoromethoxyphenyl) ethylidene] amine melting point 177.8-180.1 ° C.

Example 512
(S) -N-Cyclohexylidene-N- [4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] amine Mp 178.6-179.3 ° C.

Example 513
N- (2-benzylideneheptylidene) -N- [4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] Amine mp 166.6-169.6 ° C.

Example 514
(S) -N- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] -N- (4-tri) Preparation of Fluoromethylbenzyl) amine (S) -N- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) prepared in Example 504 Sodium borohydride (13 mg, 0.34) to a mixture of piperazin-1-yl] -N- (4-trifluoromethylbenzylidene) amine (100 mg, 0.23 mmol) and THF (4 ml) under ice-cooling The resulting mixture was added with stirring) and stirred at room temperature for 30 minutes. To the reaction solution was added 1 ml of methanol, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (n-hexane / ethyl acetate = 2/1) to give (S) -N- [4- (2-methyl-6-nitro-2,3-dihydro] as pale yellow powdery crystals. Imidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] -N- (4-trifluoromethylbenzyl) amine (32 mg, 31% yield) was obtained.
1313-135.5 ° C.

Example 515
Preparation of (S) -4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-ylamine dihydrochloride Prepared according to example 503 (S)-[4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] carbamic acid tert-butyl ester (300 mg) A mixture of 0.78 mmol), 2 ml of concentrated hydrochloric acid and methanol (4 ml) was stirred at 50 ° C. for 30 minutes. The reaction solution was returned to room temperature and concentrated under reduced pressure. The residue is recrystallized from methanol / ether and (S) -4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine in yellow powder crystals. 1-ylamine dihydrochloride (265 mg, 91% yield) was obtained.
Melting point 176 ° C (decomposition).

Example 516
3- [3- (2-Chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] -5- (4-trifluoromethoxyphenyl) -3H- [1,3,4] Preparation of oxadiazol-2-one 2-chloro-4-nitro-1H-imidazole (2.21 g, 14.98 mmol) and 3- (2-methyl-2-oxiranylmethyl) -5- (4 Sodium bicarbonate (1.32 g,) in a suspension of ethanol (25 ml) in trifluoromethoxyphenyl) -3H- [1,3,4] oxadiazol-2-one (2.37 g, 7.49 mmol) 15.73 mmol) was added and heated to reflux for 8 hours. Water is added to the reaction solution, and the mixture is extracted with methylene chloride, dried over magnesium sulfate, concentrated under reduced pressure, and slightly yellow amorphous 3- [3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxyl -2-Methylpropyl] -5- (4-trifluoromethoxyphenyl) -3H- [1,3,4] oxadiazol-2-one (3.27 g, 94% yield) was obtained.
¹ H-NMR (DMSO-d ₆ ) δ ppm:
1.53 (3 H, s), 3.67 (1 H, d, J = 8.8 Hz), 3.81 (1 H, d, J = 8.8 Hz), 4.49 (2 H, s), 7. 42-7.66 (2H, m), 7.86-8.09 (2H, m), 8.54 (1 H, s), 10. 98 (1 H, br).

  The compounds of Example 517 to Example 523 shown in the following table were produced in the same manner as in Example 516 using the corresponding starting materials.

Example 524
3- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -5- (4-trifluoromethoxyphenyl) -3H- [1,3,4 Preparation of Oxadiazol-2-one 3- [3- (2-Chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] -5- (4 prepared in Example 516) Hydrogen under stirring with ice-cooling in a solution of trifluoromethoxyphenyl) -3H- [1,3,4] oxadiazol-2-one (3.27 g, 7.05 mmol) in 1,4-dioxane (70 ml) Sodium fluoride (0.37 g, 9.17 mmol) was added and heated to reflux for 3 hours. The reaction mixture was concentrated under reduced pressure, ice-cooled, water was added, and the mixture was extracted with ethyl acetate, dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 4/1), recrystallized with acetonitrile and ethanol, and white solid 3- (2-methyl-6-nitro-2,3-dihydroimidazo [ 2,1-b] oxazol-2-ylmethyl) -5- (4-trifluoromethoxyphenyl) -3H- [1,3,4] oxadiazol-2-one (1.43 g, yield 48%) I got
Melting point 190-191 [deg.] C.

  The compounds of Example 525 to Example 531 were produced in the same manner as in Example 524 using the corresponding starting materials.

Example 525
3- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -5- (4-trifluoromethylphenyl) -3H- [1,3,4 Mp 230-231 ° C.

Example 526
3- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -5- (biphenyl-4-yl) -3H- [1,3,4] Oxadiazol-2-one mp 248-249 ° C.

Example 527
3- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -5- (4-chlorophenyl) -3H- [1,3,4] oxadi Azol-2-one mp 221-222 ° C.

Example 528
3- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -5- (4-fluorophenyl) -3H- [1,3,4] oxa Diazole-2-one melting point 188-191 [deg.] C.

Example 529
3- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -5- [2- (4-chlorophenyl) vinyl] -3H- [1,3 , 4] Oxadiazol-2-one Melting point 249-252 ° C.

Example 530
3- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -5- [2- (4-chlorophenyl) ethyl] -3H- [1,3 , 4] Oxadiazol-2-one mp 139-140 ° C.

Example 531
3- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -5- (4-chlorophenoxymethyl) -3H- [1,3,4] Oxadiazol-2-one mp 64-66 ° C.

Example 532
3- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -5-phenyl-3H- [1,3,4] oxadiazole-2- Preparation of on 2-Chloro-4-nitro-1H-imidazole (170 mg, 1.15 mmol), 3- (2-methyl-2-oxiranylmethyl) -5-phenyl-3H- [1,3,4 A mixture of oxadiazol-2-one (310 mg, 0.9 mmol), sodium hydrogen carbonate (120 mg, 1.43 mmol) and ethanol (2 ml) was heated to reflux for 2.5 hours. The reaction solution is returned to room temperature, water is added, extraction is performed with methylene chloride, drying is performed using magnesium sulfate, and filtration is performed. The filtrate was concentrated under reduced pressure. The residue was dissolved in 1,4-dioxane (10 ml), sodium hydride (55 mg, 1.38 mmol) was added, and the mixture was stirred at room temperature for 1 hour and then heated to reflux for 1.5 hours. The reaction solution is returned to room temperature, water is added, extraction is performed with methylene chloride, drying is performed using magnesium sulfate, and filtration is performed. The filtrate was concentrated under reduced pressure. The residue is recrystallised from ethanol and 3- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -5-phenyl-3H- [3- (2-methyl-6-nitro-2,3-dihydroimidazo) as a pale tea powder. 1, 3, 4] Oxadiazol-2-one (127 mg, 32% yield) was obtained.
Melting point 225-227 [deg.] C.

Example 533
5- (4-chlorobenzyl) -3- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -3H- [1,3,4] oxa Preparation of Diazol-2-one 4-Methylbenzenesulfonic acid 2-methyl-2-oxiranylmethyl ester (3.98 g, 18.9 mmol), 5- (4-chlorobenzyl) -3H- [1,1 3,4] oxadiazol-2-one (5.5 g, 26.11 mmol), potassium carbonate (3.4 g, 24.6 mmol), sodium iodide (3.4 g, 22.68 mmol), DMF The mixture of (40 ml) was stirred at room temperature for 21 hours. Water was added to the reaction solution and extracted twice with ethyl acetate. The organic phases were combined, washed three times with water, dried over magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to give 5.47 g of a yellow oil.

2.3 g (11.02 mmol) of this yellow oil, 2,4-dinitro-1H-imidazole (2.26 g, 14.3 mmol), sodium acetate (1.81 g, 22.07 mmol) and ethanol The mixture of (22 ml) was heated to reflux for 8 hours. The reaction solution is cooled to room temperature, water is added, extraction is performed with ethyl acetate, the extract is washed with saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 3/1) to give 5- (4-chlorobenzyl) -3- (2-methyl-6-nitro-2,3-dihydroimidazo) as a white solid. [2,1-b] oxazol-2-ylmethyl) -3H- [1,3,4] oxadiazol-2-one (240 mg, 9%) was obtained.
Melting point 151-153 [deg.] C.

Example 534
5- (4-Bromophenyl) -3- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -3H- [1,3,4] oxa Preparation of Diazol-2-one The methanesulfonic acid 2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl ester prepared in Example 41 (1.02 g, 3.67 mmol), 5- (4-bromophenyl) -3H- [1,3,4] oxadiazol-2-one (680 mg, 2.82 mmol), potassium carbonate (580 mg, 4.2 mmol) A mixture of sodium iodide (890 mg, 5.94 mmol) and DMF (15 ml) was stirred at 100 ° C. for 3 hours. The reaction solution was cooled to room temperature, water was added, and the mixture was extracted twice with ethyl acetate. The organic phases were combined, washed three times with water, dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo. The residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 9/1) to give 5- (4-bromophenyl) -3- (2-methyl-6-nitro-2,3-dihydro) as a slightly yellow powder. Imidazo [2,1-b] oxazol-2-ylmethyl) -3H- [1,3,4] oxadiazol-2-one (17.4 mg, 2% yield) was obtained.
Mp 231-233 ° C.

Example 535
5- (4-bromophenyl) -3- (6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -3H- [1,3,4] oxadiazole-2 Methanesulfonic acid 6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl ester (3.28 g, 12.46 mmol) prepared in Example 40 and 5- By the method of Example 534 using (4-bromophenyl) -3H- [1,3,4] oxadiazol-2-one (1.5 g, 6.22 mmol), 5- (light yellow powder) 4-Bromophenyl) -3- (6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -3H- [1,3,4] oxadiazol-2-one ( 312 mg, yield 12%) Obtained.
Melting point 264 ° C (decomposition).

  The compound of Example 536 was produced in the same manner as in Example 535 using the corresponding starting materials.

Example 536
3- (6-Nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -5- (4-trifluoromethoxyphenyl) -3H- [1,3,4] oxadiazole -2-one melting point 204-207 ° C.

Example 537
3- [2- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-yl) ethyl] -5- (pyridin-4-yl) -3H- [1 Preparation of 5,3,4] Oxadiazol-2-one 5- (Pyridin-4-yl) -3H- [1,3,4] oxadiazol-2-one (150 mg, 0.92 mmol), hydrogen A mixture of sodium fluoride (41 mg, 1.03 mmol) and DMF (1.5 ml) was stirred at room temperature for 1 hour. In the reaction solution, methanesulfonic acid 2- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-yl) ethyl ester (200 mg, 0.1%) prepared in Example 42 was prepared. 69 mmol) and sodium iodide (140 mg, 0.93 mmol) were sequentially added, and the mixture was stirred at 50-60 ° C for 6 hours. The reaction solution was cooled to room temperature, water was added, and the mixture was extracted twice with ethyl acetate. The organic phases were combined, washed three times with water, dried over magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 25/1) to give 3- [2- (2-methyl-6-nitro-2,3-dihydroimidazo) as a white powder. [2,1-b] oxazol-2-yl) ethyl] -5- (pyridin-4-yl) -3H- [1,3,4] oxadiazol-2-one (137 mg, 56% yield) I got
Melting point 147-149 [deg.] C.

  The compound of Example 538 was produced in the same manner as in Example 537, using the corresponding starting materials.

Example 538
3- [2- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-yl) ethyl] -5- (pyrazin-2-yl) -3H- [1 , 3,4] Oxadiazol-2-one mp 209-212 ° C.

Example 539
(R) -3- [3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] -5- (4-trifluoromethoxyphenyl) -3H- [1,1 Preparation of 3,4] Oxadiazol-2-one 5- (4-Trifluoromethoxyphenyl) -3H- [1,3,4] oxadiazol-2-one (0.68 g, 2.76 mmol) And a solution of (R) -2-chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitroimidazole (0.50 g, 2.30 mmol) prepared in Example 12 in DMF (5 ml) To the mixture was added potassium carbonate (0.38 g, 2.76 mmol) and stirred at room temperature for 16 hours. Water was added, extracted with ethyl acetate, dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 4/1) to give white amorphous (R) -3- [3- (2-chloro-4-nitroimidazol-1-yl) -2- Hydroxy-2-methylpropyl] -5- (4-trifluoromethoxyphenyl) -3H- [1,3,4] oxadiazol-2-one (1.06 g, quantitative) was obtained.
¹ H-NMR (DMSO-d ₆ ) δ ppm:
1.53 (3 H, s), 3.67 (1 H, d, J = 8.8 Hz), 3.81 (1 H, d, J = 8.8 Hz), 4.49 (2 H, s), 7. 42-7.66 (2H, m), 7.86-8.09 (2H, m), 8.54 (1 H, s), 10. 98 (1 H, br).

Example 540
(R) -3- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -5- (4-trifluoromethoxyphenyl) -3H- [1 Preparation of (3,4) Oxadiazol-2-one (R) -3- [3- (2-Chloro-4-nitroimidazol-1-yl) -2-hydroxy-2- 2 Methylpropyl] -5- (4-trifluoromethoxyphenyl) -3H- [1,3,4] oxadiazol-2-one (0.87 g, 1.88 mmol) in 1,4-dioxane (18 ml) Sodium hydride (98 mg, 2.44 mmol) was added to the solution under ice-cooling and stirring, and the mixture was heated to reflux for 5 hours. The mixture was concentrated under reduced pressure, ice-cooled, water was added, and the mixture was extracted with ethyl acetate, dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 9/1), recrystallized from acetonitrile / isopropanol, and white powder crystals of (R) -3- (2-methyl-6-nitro-2, 3-Dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -5- (4-trifluoromethoxyphenyl) -3H- [1,3,4] oxadiazol-2-one (0.32 g, The yield was 40%).
Optical purity 98.2% ee
[Α] _D ²⁶ = -12.43 ° (concentration: 0.668, CHCl ₃ )
Melting point 146-148 [deg.] C.

Example 541
Preparation of 3- [3- (2-Chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] -3H-benzoxazol-2-one 2-Chloro-4-nitro-1H- In a suspension of imidazole (503 mg, 3.41 mmol), 3- (2-methyl-2-oxiranylmethyl) -3H-benzoxazol-2-one (700 mg, 3.41 mmol) in ethanol (7 ml) Sodium acetate (336 mg, 4.1 mmol) was added and heated to reflux for 8 hours. The reaction solution is returned to room temperature, water is added, extraction is performed with methylene chloride, drying is performed using magnesium sulfate, and filtration is performed. The filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (methylene chloride / methanol = 30/1) to give 3- [3- (2-chloro-4-nitroimidazole-1-) as a slightly yellow powder. Y) -2-hydroxy-2-methylpropyl] -3H-benzoxazol-2-one (616 mg, 51% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1. 31 (3 H, s), 3.0 4 (1 H, s), 3. 87 (1 H, d, J = 14.7 Hz), 3.98 (1 H, d, J = 14.7 Hz), 4. 13 (1 H, d, J = 12.5 Hz), 4.24 (1 H, d, J = 14.5 Hz), 7.08-7. 31 (4 H, m), 8.04 (1 H, s).

  The compounds of Example 542 and Example 543 shown in the following table were produced in the same manner as in Example 541 using the corresponding starting materials.

Example 544
Preparation of 3- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -3H-benzoxazol-2-one 3- (2-Chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] -3H-benzoxazol-2-one (615 mg, 1.74 mmol), sodium hydride (76. A mixture of 6 mg, 1.91 mmol), 1,4-dioxane (15 ml) was heated to reflux for 1 h. The reaction solution is returned to room temperature, water is added, extraction is performed with methylene chloride, drying is performed with sodium sulfate, and filtration is performed. The filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (methylene chloride / methanol = 30/1) to give 3- (2-methyl-6-nitro-2,3-dihydroimidazo [white powder] as a white powder. 2,1-b] oxazol-2-ylmethyl) -3H-benzoxazol-2-one (209 mg, 38% yield) was obtained.
Melting point 222.7-224.3 ° C.

  The compounds of Example 545 and Example 546 were produced in the same manner as in Example 544, using the corresponding starting materials.

Example 545
5-chloro-3- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -3H-benzoxazol-2-one melting point 207.6-207. 9 ° C.

Example 546
5-fluoro-3- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -3H-benzoxazol-2-one melting point 246.2-246. 8 ° C.

Example 547
Preparation of 5-bromo-3- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -3H-benzoxazol-2-one 2-chloro-4 -Nitro-1H-imidazole (3.22 g, 21.8 mmol), 5-bromo-3- (2-methyl-2-oxiranylmethyl) -3H-benzoxazol-2-one (6.2 g, 21 .8 mmol), a mixture of sodium acetate (1.97 g, 24 mmol), ethanol (50 ml) was heated to reflux for 8 hours. The reaction solution was returned to room temperature and concentrated under reduced pressure. To the residue was added water, extracted with methylene chloride, dried over magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, the residue was dissolved in 60 ml of 1,4-dioxane, sodium hydride (528 mg, 13.21 mmol) was added, and the mixture was stirred at 70-80 ° C. for 17 hours. The reaction solution was returned to room temperature and concentrated under reduced pressure. To the residue was added water, extracted with methylene chloride, dried over magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (methylene chloride / methanol = 30/1) to give 5-bromo-3- (2-methyl-6-nitro-2,3) as a white powder. -Dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -3H-benzoxazol-2-one (1.82 g, yield 37%) was obtained.
Melting point 243-245.5 ° C.

Example 548
Preparation of 5- (2-chloro-4-nitroimidazol-1-ylmethyl) -3- (4-hydroxybiphenyl-3-yl) -5-methyloxazolidin-2-one 2-chloro-4-nitro-1H- Imidazole (1.3 g, 8.78 mmol), 5-phenyl-3- (2-methyl-2-oxiranylmethyl) -3H-benzoxazol-2-one (2.47 g, 8.78 mmol), A mixture of sodium acetate (792 mg, 9.66 mmol) and ethanol (30 ml) was heated to reflux for 10 hours. The reaction solution was returned to room temperature and concentrated under reduced pressure. To the residue was added water, extracted with methylene chloride, dried over magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (methylene chloride / methanol = 10/1) to give 5- (2-chloro-4-nitroimidazol-1-ylmethyl) -3- (4 of white powder) -Hydroxy-3-biphenylyl) -5-methyloxazolidin-2-one (1.82 g, 61% yield) was obtained.
¹ H-NMR (DMSO-d ₆ ) δ ppm:
1.55 (3 H, s), 3.85 (1 H, d, J = 9.5 Hz), 3.98 (1 H, d, J = 9.5 Hz), 4.46 (1 H, d, J = 14) .9 Hz), 4.56 (1 H, d, J = 14.9 Hz), 6.99 (1 H, d, J = 8.4 Hz), 7.27 (1 H, t, J = 7.3 Hz), 7 36-7.57 (6H, m), 8.52 (1 H, s), 10.06 (1 H, s).

Example 549
Preparation of 3- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -5-phenyl-3H-benzoxazol-2-one Prepared as in Example 548 5- (2-chloro-4-nitroimidazol-1-ylmethyl) -3- (4-hydroxy-3-biphenylyl) -5-methyloxazolidin-2-one (1.23 g, 2.88 mmol), hydrogen A mixture of sodium fluoride (127 mg, 3.16 mmol) and DMF (10 ml) was stirred at 100 ° C. for 4 hours. The reaction solution was returned to room temperature and concentrated under reduced pressure. To the residue was added water and extracted with methylene chloride. The organic phase was washed with water, then with brine, dried over magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (methylene chloride / methanol = 20/1) to give 3- (2-methyl-6-nitro-2,3-dihydroimidazo [2] as yellow-brown powdery crystals. 1,1-b] oxazol-2-ylmethyl) -5-phenyl-3H-benzoxazol-2-one (172 mg, 15% yield) was obtained.
Melting point 254-44.6 ° C.

Example 550
Preparation of 3- [2- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-yl) ethyl] -3H-benzoxazol-2-one 2-benzooxa A mixture of zolinone (240 mg, 1.8 mmol), sodium hydride (67 mg, 1.95 mmol) and DMF (10 ml) was stirred at room temperature for 30 minutes. In the reaction solution, methanesulfonic acid 2- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-yl) ethyl ester (500 mg, 1.7) prepared in Example 42 was prepared. Add millimoles) and stir at 50-60 ° C. for 4 hours. The reaction was brought to room temperature and poured into ice water. Precipitated crystals are collected by filtration and recrystallized from ethanol to obtain 3- [2- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole-2-) of pale tea powder. Y) ethyl] -3H-benzoxazol-2-one (320 mg, 56% yield) was obtained.
Mp 193-195 ° C.

Example 551
Preparation of 3- [5- (2-chloro-4-nitroimidazol-1-yl) -4-hydroxy-4-methylpentyl] -3H-benzoxazol-2-one 3- [3- (2-methyl-) By the method of Example 541, using 2-oxiranyl) propyl] -3H-benzoxazol-2-one (3.8 g, 16.3 mmol), 3- [5- (2-chloro-4-chloro-4-amino-4-hydroxy-4-hydroxy-4-hydroxy-4-hydroxy-4-hydroxy-4-hydroxy-4-hydroxy it Nitroimidazol-1-yl) -4-hydroxy-4-methylpentyl] -3H-benzoxazol-2-one (3.5 g, 68%) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.20 (3H, s), 1.49-1.70 (2H, m), 1.88-2.07 (2H, m), 2.68 (1 H, s), 3.81-3. 93 (2H, m), 4.00 (2 H, s), 6.98 (1 H, d, J = 7.3 Hz), 7.09-7.26 (3 H, m), 8.00 (1 H, 1 H, m) s).

Example 552
Preparation of 3- [6- (2-chloro-4-nitroimidazol-1-yl) -5-hydroxy-5-methylhexyl] -3H-benzoxazol-2-one 3- [4- (2-methyl-) By the method of Example 541 using 2-oxiranyl) butyl] -3H-benzoxazol-2-one (1.2 g, 4.86 mmol), 3- [6- (2-chloro-4-) Nitroimidazol-1-yl) -5-hydroxy-5-methylhexyl] -3H-benzoxazol-2-one (1.2 g, 62%) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.16 (3H, s), 1.38-1.58 (4H, m), 1.67-1. 86 (2H, m), 2.15 (1 H, s), 3.87 (2H, 2H, s) t, J = 6.6 Hz), 3.98 (2 H, s), 6. 98 (1 H, d, J = 7.8 Hz), 7.08-7.26 (3 H, m), 8.01 ( 1 H, s).

Example 553
Preparation of 3- [3- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-yl) propyl] -3H-benzoxazol-2-one Example 551 3- [5- (2-Chloro-4-nitroimidazol-1-yl) -4-hydroxy-4-methylpentyl] -3H-benzoxazol-2-one prepared (3.5 g, 9.2 mmol) According to the method of Example 544, 3- [3- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-yl) propyl]-of pale yellow powder is 3H-benzoxazol-2-one (2.4 g, 76% yield) was obtained.
Melting point 180-181 [deg.] C.

Example 554
Preparation of 3- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-yl) butyl] -3H-benzoxazol-2-one Example 552 Using 3- [6- (2-chloro-4-nitroimidazol-1-yl) -5-hydroxy-5-methylhexyl] -3H-benzoxazol-2-one (1.2 g, 3 mmol) prepared According to the method of Example 544, 3- [4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-yl) butyl] -3H- of a slightly yellow powder. Benzooxazol-2-one (780 mg, 72% yield) was obtained.
Melting point 155-158 [deg.] C.

Working Example 555
Preparation of 1- [3- (2-Chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] -3-methyl-1,3-dihydrobenzimidazol-2-one 1-methyl White powder crystals by the method of Example 541 using -3- (2-methyl-2-oxiranylmethyl) -1,3-dihydrobenzimidazol-2-one (1.41 g, 6.46 mmol) 1- [3- (2-Chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] -3-methyl-1,3-dihydrobenzimidazol-2-one (1.23 g , Yield 63%).
¹ H-NMR (CDCl ₃ ) δ ppm:
1.23 (3H, s), 3.47 (3H, s), 3.94 (1 H, d, J = 12.4 Hz), 4.03 (1 H, d, J = 12.4 Hz), 4. 06 (1 H, d, J = 11.9 Hz), 4.17 (1 H, d, J = 11.9 Hz), 4.79 (1 H, s), 7.00-7.21 (4 H, m), 8.09 (1 H, s).

  The compounds of Example 556 to Example 565 shown in the following table were produced in the same manner as in Example 555, using the corresponding starting materials.

Example 566
Preparation of 1-Methyl-3- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -1,3-dihydrobenzimidazol-2-one 1- [3- (2-Chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] -3-methyl-1,3-dihydrobenzimidazol-2-one (prepared by 555) 1.23 g (3.37 mmol) of 1-methyl-3- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] according to the method of Example 544 using ] Oxazol-2-ylmethyl) -1,3-dihydrobenzimidazol-2-one (563 mg, 51% yield) was obtained.
Mp 203.2-204.4 ° C.

  The compounds of Example 567 to Example 576 were produced in the same manner as in Example 566, using the corresponding starting materials.

Example 567
1- (1-tert-butoxycarbonylpiperidin-4-yl) -3- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -1,3 -Dihydrobenzimidazole-2-one mp 218-219.1 <0> C.

Example 568
5-chloro-1-methyl-3- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -1,3-dihydrobenzimidazol-2-one Melting point 261.9-265.4 ° C (decomposition).

Example 569
1-methyl-3- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -5-trifluoromethyl-1,3-dihydrobenzimidazole-2 -Melting point 232.4-234.7 <0> C.

Example 570
6-Chloro-1-methyl-3- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -1,3-dihydrobenzimidazol-2-one Melting point 261.3-263.3 ° C.

Example 571
5-fluoro-1-methyl-3- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -1,3-dihydrobenzimidazol-2-one Melting point 244.2-249.8 ° C (decomposition).

Example 572
5-chloro-1-ethyl-3- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -1,3-dihydrobenzimidazol-2-one Melting point 240.9-245.6 ° C.

Example 573
5-chloro-1-isopropyl-3- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -1,3-dihydrobenzimidazol-2-one Melting point 240.5-244.8 ° C.

Example 574
5-dimethylamino-1-methyl-3- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -1,3-dihydrobenzimidazole-2- On melting point 264.6-268.3 ° C (decomposition).

Example 575
5-chloro-1- (n-hexyl) -3- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -1,3-dihydrobenzimidazole -2-one melting point 168.1-169.3 ° C.

Example 576
5-Ethoxycarbonyl-1-methyl-3- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -1,3-dihydrobenzimidazole-2- Mp 265.8-266.7 ° C.

Example 577
Preparation of 1- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -3-phenyl-1,3-dihydrobenzimidazol-2-one 1- The white powdery crystals were obtained by the method of Example 200 using (2-methyl-2-oxiranylmethyl) -3-phenyl-1,3-dihydrobenzimidazol-2-one (758 mg, 2.7 mmol). 70 mg of 1- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -3-phenyl-1,3-dihydrobenzimidazole-2-one The rate is 13%).
Mp 234.5-234.7 ° C.

  The compound of Example 578 was produced in the same manner as in Example 577, using the corresponding starting materials.

Example 578
1- (4-Fluorophenyl) -3- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -1,3-dihydrobenzimidazole-2- Melting point 254.1-254.7 ° C.

Example 579
1- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl)-(3-piperidin-4-yl) -1,3-dihydrobenzimidazole-2 Preparation of 1- (1-tert-butoxycarbonylpiperidin-4-yl) -3- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] prepared in Example 567 A mixture of oxazol-2-ylmethyl) -1,3-dihydrobenzimidazol-2-one (371 mg, 0.74 mmol), 1 ml of trifluoroacetic acid and methylene chloride (10 ml) was stirred at room temperature for 2 hours. The reaction solution was concentrated under reduced pressure. Saturated aqueous sodium bicarbonate solution was added to the residue to make it basic, and the precipitated crystals were collected by filtration. By repeatedly washing the precipitated crystals with water, it is possible to obtain 1- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -3- (piperidine) as pale yellow powder crystals. 4-yl) -1,3-dihydrobenzimidazol-2-one (255 mg, 86% yield) was obtained.
Melting point 192.3-198.8 ° C (decomposition).

Example 580
4- [3- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -2-oxo-2,3-dihydrobenzimidazol-1-yl] Preparation of piperidine-1-carboxylic acid benzyl ester 1- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -3- (prepared according to Example 579 To a mixture of piperidin-4-yl) -1,3-dihydrobenzimidazol-2-one (90 mg, 0.23 mmol) and methylene chloride (5 ml) under ice-cooling triethylamine (75 mg, 0.74 mmol) And benzyl chloroformate (126 mg, 0.74 mmol) were sequentially added, and the mixture was stirred at room temperature for 3 hours. The reaction solution was washed successively with water, saturated aqueous sodium bicarbonate solution and saturated brine, dried over magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (n-hexane / acetone = 1/1) to give 4- [3- (2-methyl-6-nitro-2, white powder crystal] 3-Dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -2-oxo-2,3-dihydrobenzimidazol-1-yl] piperidine-1-carboxylic acid benzyl ester (25 mg, 21% yield) I got
Melting point 181.7-184.6 [deg.] C.

Example 581
Preparation of 1-benzyl-3- [3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] imidazolidin-2-one 1-benzyl-3- (2- By the method of Example 541 using methyl-2-oxiranylmethyl) imidazolidin-2-one (680 mg, 2.76 mmol), 1-benzyl-3- [3- (2-chloro) as white powder crystals. 4-Nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] imidazolidin-2-one (580 mg, 59% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.18 (3H, s), 3.17-3.54 (6H, m), 4.07 (2H, s), 4.37 (2H, s), 7.17-7.40 (5H, 5) m), 8.13 (1 H, s).

  The compounds of Example 582 to Example 587 shown in the following table were produced in the same manner as in Example 581 using the corresponding starting materials.

Example 588
Preparation of 1-Benzyl-3- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) imidazolidin-2-one Prepared as in Example 581 Example using benzyl 3- [3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] imidazolidin-2-one (580 mg, 1.47 mmol) According to the method of 544, 1-benzyl-3- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) imidazolidin-2-one of white powdery crystals. (395 mg, 75% yield) were obtained.
Melting point 180.2-180.9 ° C.

  The compounds of Example 589 to Example 594 were produced in the same manner as in Example 588, using the corresponding starting materials.

Example 589
1- (4-Fluorobenzyl) -3- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) imidazolidin-2-one melting point 182.5- 183.3 ° C.

Example 590
1- (4-bromobenzyl) -3- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) imidazolidin-2-one melting point 205.7- 208.1 ° C.

Example 591
1- (4-methoxybenzyl) -3- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) imidazolidin-2-one melting point 158.6- 160.5 ° C.

Example 592
1- (4-chlorobenzyl) -3- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) imidazolidin-2-one melting point 208.7- 209.8 ° C.

Example 593
1- (1-benzylpiperidin-4-yl) -3- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) imidazolidin-2-one
¹ H-NMR (CDCl ₃ ) δ ppm:
1.41-1.72 (7H, m), 1.97-2.10 (2H, m), 2.88-2.95 (2H, m), 3.08-3. 30 (4H, m) ), 3.43 to 3.70 (4H, m), 3.81 (1H, d, J = 15.0 Hz), 3.91 (1H, d, J = 10.3 Hz), 4.51 (1H) , D, J = 10.3 Hz), 7.17-7.31 (5 H, m), 7.47 (1 H, s).

Working Example 594
1- (2,4-Dimethoxybenzyl) -3- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) imidazolidin-2-one melting point 175- 175.4 ° C.

Example 595
Preparation of 1- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -3-phenylimidazolidin-2-one 1- (2-methyl-2) White powder crystals of 1- (2-methyl-6-nitro-2) by the method of Example 200 using -oxiranylmethyl) -3-phenylimidazolidin-2-one (300 mg, 1.29 mmol) 3, 3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -3-phenylimidazolidin-2-one (59 mg, 26% yield) was obtained.
Mp 194.8-197.4 ° C.

Example 596
Preparation of 1- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) imidazolidin-2-one 1- (2,4) prepared in Example 594 -Dimethoxybenzyl) -3- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) imidazolidin-2-one (100 mg, 0.24 mmol), A mixture of 2 ml of trifluoroacetic acid and methylene chloride (2 ml) was stirred at room temperature for 1 hour. The reaction mixture was neutralized with saturated aqueous sodium bicarbonate solution, extracted with methylene chloride, dried over sodium sulfate and filtered. The filtrate is concentrated under reduced pressure, and the crystals obtained by treating the residue with diethyl ether are collected by filtration to give 1- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1 of white powder crystals] -B] oxazol-2-ylmethyl) imidazolidin-2-one (50 mg, yield 78%) was obtained.
Melting point 224.8-229.1 ° C (decomposition).

Example 597
Preparation of 3- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) oxazolidin-2-one 3- (2-methyl-2-oxiranylmethyl) ) Oxazolidin-2-one (2.87 g, 18.23 mmol), 2-chloro-4-nitro-1H-imidazole (2.7 g, 18.23 mmol), sodium acetate (1.64 g, 20.05 mmol) ) And ethanol (30 ml) were heated to reflux for 10 hours. The reaction solution was returned to room temperature and concentrated under reduced pressure. To the residue is added methylene chloride, and the mixture is washed successively with water, saturated aqueous sodium bicarbonate solution and saturated brine, dried over magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, the residue was dissolved in 50 ml of 1,4-dioxane, sodium hydride (610 mg, 15.25 mmol) was added and heated to reflux overnight. The reaction solution was returned to room temperature and concentrated under reduced pressure. To the residue was added water, extracted with methylene chloride, dried over magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (methylene chloride / methanol = 20/1) to give 3- (2-methyl-6-nitro-2,3-dihydroimidazo [white powder] as a white powder. 2,1-b] oxazol-2-ylmethyl) oxazolidin-2-one (1.54 g, 40% yield) was obtained.
¹ H-NMR (DMSO-d ₆ ) δ ppm:
1.59 (3 H, s), 3.46 to 3.71 (4 H, m), 4.11 to 4.30 (4 H, m), 8.15 (1 H, s).

Example 598
Preparation of 5-azidomethyl-3- [3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] oxazolidin-2-one 2-chloro-4-nitro-1H- Imidazole (350 mg, 2.37 mmol), 5-azidomethyl-3- (2-methyl-2-oxiranylmethyl) oxazolidin-2-one (500 mg, 2.37 mmol), sodium acetate (214 mg, 2.61) A mixture of mmol) and ethanol (5 ml) was stirred at 70 ° C. for 8 hours. The reaction solution was returned to room temperature and concentrated under reduced pressure. To the residue was added water, extracted with methylene chloride, dried over sodium sulfate and filtered. The filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (n-hexane / ethyl acetate = 1/2) to give 5-azidomethyl-3- [3- (2-chloro-) as a slightly yellow oil. 4-Nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] oxazolidin-2-one (640 mg, 75% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.23 (3H, s), 3.17-3.35 (2H, m), 3.43-3.61 (2H, m), 3.67-3.84 (2H, m), 4.. 01-4.16 (2H, m), 4.68-4.81 (1 H, m), 8.04 (1 H, s).

Example 599
Preparation of 5-azidomethyl-3- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) oxazolidin-2-one 5-azidomethyl prepared in Example 598 -3- [3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] oxazolidin-2-one (1 g, 2.78 mmol) in 10 ml of 1,4-dioxane The mixture was then added with sodium hydride (130 mg, 3.25 mmol) and stirred at 80.degree. C. for 4 hours. The reaction solution was returned to room temperature, water was added, and the mixture was concentrated under reduced pressure. To the residue was added water, extracted with methylene chloride, dried over sodium sulfate and filtered. The filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 20/1) to give 5-azidomethyl-3- (2-methyl-6-nitro-) as pale brown powdery crystals. 2,3-Dihydroimidazo [2,1-b] oxazol-2-ylmethyl) oxazolidin-2-one (46 mg, 5% yield) was obtained.
MS 323 (M ⁺ )
Example 600
1- [3- (2-Chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] -1,4-dihydrobenzo [d] [1,3] oxazin-2-one Preparation Example using 1- (2-methyl-2-oxiranylmethyl) -1,4-dihydrobenzo [d] [1,3] oxazin-2-one (5.13 g, 23.04 mmol) The method of 541 gives 1- [3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] -1,4-dihydrobenzo [d] [1] as a slightly yellow oil. 1,3] oxazin-2-one (1.54 g, 36% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.23 (3 H, s), 3.96 (1 H, br), 4.04-4. 20 (4 H, m), 5. 28 (2 H, s), 7.00-7.07 (1 H, s) m), 7.11-7.24 (2H, m), 7.30-7. 43 (1 H, m), 8.07 (1 H, s).

Example 601
1- (2-Methyl-6-nitro 2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -1,4-dihydrobenzo [d] [1,3] oxazin-2-one Preparation 1- [3- (2-Chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] -1,4-dihydrobenzo [d] [1,3 prepared in Example 600 By the method of Example 544 using oxazin-2-one (1.54 g, 4.20 mmol), 1- (2-methyl-6-nitro-2,3-dihydroimidazo [2,2] as a slightly brown solid. 1-b] oxazol-2-ylmethyl) -1,4-dihydrobenzo [d] [1,3] oxazin-2-one (0.58 g, 42% yield) was obtained.
Melting point 230-231 [deg.] C.

Example 602
Preparation of 1- [3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] -3,3-difluoro-1,3-dihydroindol-2-one 3, White according to the method of Example 541 using 3-difluoro-1- (2-methyl-2-oxiranylmethyl) -1,3-dihydroindol-2-one (1.14 g, 4.76 mmol) Powdered 1- [3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] -3,3-difluoro-1,3-dihydroindol-2-one (968 mg , Yield 53%).
¹ H-NMR (DMSO-d ₆ ) δ ppm:
1.09 (3 H, s), 3. 73 (1 H, d, J = 14.5 Hz), 3.87 (1 H, d, J = 14.5 Hz), 4. 13 (1 H, d, J = 14) .4 Hz), 4.21 (1 H, d, J = 14.4 Hz), 5.39 (1 H, s), 7.20-7.26 (1 H, m), 7.33-7.37 (1 H) , M), 7.57-7.64 (1 H, m), 7.67-7. 71 (1 H, m).

  The compounds of Example 603 to Example 604 shown in the following table were produced in the same manner as in Example 602, using the corresponding starting materials.

Example 605
Preparation of 3,3-Difluoro-1- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -1,3-dihydroindol-2-one 1- [3- (2-Chloro-4-nitroimidazol-1-yl) -2hydroxy-2-methylpropyl] -3,3-difluoro-1,3-dihydroindol-2-one prepared in Example 602 (903 mg, 2.34 mmol) according to the method of example 544 using 3,3-difluoro-1- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] according to the method of example 544 ] Oxazol-2-ylmethyl) -1,3-dihydroindol-2-one (77 mg, 9% yield) was obtained.
Melting point 202-206 [deg.] C.

  The compound of Example 606 was produced in the same manner as in Example 605, using the corresponding starting materials.

Example 606
3,3-Dimethyl-1- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -1,3-dihydroindol-2-one
¹ H-NMR (DMSO-d ₆ ) δ ppm:
1.25 (3 H, s), 1.37 (3 H, s), 1.78 (3 H, s), 3.96 (1 H, d, J = 15.1 Hz), 4.00 (1 H, d, J = 10.7 Hz), 4.22 (1 H, d, J = 15.1 Hz), 4.57 (1 H, d, J = 10.7 Hz), 7.04-7.17 (3 H, m), 7.24-7.31 (1 H, m), 7.44 (1 H, s).

Example 607
Preparation of 1- (2-Chloro-4-nitroimidazol-1-yl) -4- (1-ethyl-1H-tetrazol-5-yl) -2-methylbutan-2-ol 1-ethyl-5- [2 By the method of Example 541 using 1- (2-methyl-2-oxiranyl) ethyl] -1H-tetrazole (1.04 g, 5.59 mmol), 1- (2-chloro-4-l of a slightly yellow oil Nitroimidazol-1-yl) -4- (1-ethyl-1H-tetrazol-5-yl) -2-methylbutan-2-ol (1.15 g, yield 69%) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.29 (3H, s), 1.56 (3H, t, J = 7.3 Hz), 2.04-2.22 (2H, m), 2.91-3.11 (2H, m), 4.10 (2H, s), 4.24 (1 H, br), 4.34 (2 H. q, J = 7.3 Hz), 8.09 (1 H, s).

  The compounds of Example 608 and Example 609 shown in the following Table were prepared in the same manner as in Example 607, using the corresponding starting materials.

Example 610
Preparation of 2- [2- (1-Ethyl-1H-tetrazol-5-yl) ethyl] -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole Prepared as in Example 607 1- (2-Chloro-4-nitroimidazol-1-yl) -4- (1-ethyl-1H-tetrazol-5-yl) -2-methylbutan-2-ol (1.15 g, 3.49 mmol) ) And 2- [2- (1-ethyl-1H-tetrazol-5-yl) ethyl] -2-methyl-6-nitro-2,3-dihydro as a pale yellow powder crystal according to the method of Example 544. Imidazo [2,1-b] oxazole (68 mg, 7% yield) was obtained.
Melting point 135-137 [deg.] C.

  The compounds of Example 611 and Example 612 were produced in the same manner as in Example 610, using the corresponding starting materials.

Example 611
2-Methyl-6-nitro-2- [2- (1-phenyl-1H-tetrazol-5-yl) ethyl] -2,3-dihydroimidazo [2,1-b] oxazole melting point 158-159 ° C.

Example 612
2- {2- [1- (4-chlorophenyl) -1H-tetrazol-5-yl] ethyl} -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole melting point 198- 200 ° C.

Example 613
3- [2- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-yl) ethyl] -5- (4-trifluoromethylbenzylidene) thiazolidine-2, Preparation of 4-dione 2- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-yl) ethyl ester of methanesulfonic acid prepared in Example 42 (280 mg, 0 .96 mmol) and 5- (4-trifluoromethylbenzylidene) thiazolidine-2,4-dione (320 mg, 1.17 mmol) according to the method of Example 537 to obtain 3- [2- (light yellow powder) 2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-yl) ethyl] -5- (4-trifluoromethylbenzylidene) thiazo Lysine-2,4-dione (260 mg, 58% yield) was obtained. Melting point 257-258.5 [deg.] C.

Example 614
Preparation of 1- [3- (2-Chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] pyrrolidine-2,5-dione 1- (2-methyl-2-oxiranyl According to the method of Example 541 using methyl) pyrrolidine-2,5-dione (1.96 g, 11 mmol), 1- [3- (2-chloro-4-nitroimidazol-1-yl) as white powder crystal 2-Hydroxy-2-methylpropyl] pyrrolidine-2,5-dione (589 mg, 16% yield) was obtained.
¹ H-NMR (DMSO-d ₆ ) δ ppm:
0.96 (3H, s), 2.68 (4H, s), 3.48 (2H, s), 4.02 (2H, s), 5.19 (1H, s), 8.34 (1H , S).

  The compounds of Example 615 and Example 616 shown in the following table were prepared in the same manner as in Example 614, using the corresponding starting materials.

Example 617
Preparation of 1- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) pyrrolidine-2,5-dione 1- [3- prepared according to example 614 White color by the method of Example 544 using (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] pyrrolidine-2,5-dione (589 mg, 1.86 mmol) Powdered 1- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) pyrrolidine-2,5-dione (232 mg, 34% yield) is obtained. The
Melting point 202.5-203.4 [deg.] C.

  The compounds of Example 618 and Example 619 were produced in the same manner as in Example 617, using the corresponding starting materials.

Example 618
2- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) isoindole-1,3-dione mp 264.6-268.3 ° C.

Example 619
2- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -1,1-dioxo-1,2-dihydro [d] benzisothiazole-3 Melting point 243-245 ° C (decomposition).

Example 620
Preparation of 1- (2-Chloro-4-nitroimidazol-1-yl) -2- (pyridin-3-yl) -propan-2-ol 3- (2-Methyl-2-oxiranyl) pyridine (7.4 g , 54.75 mmol) and according to the method of Example 541 a white powder of 1- (2-chloro-4-nitroimidazol-1-yl) -2- (pyridin-3-yl) -propane-2- All (3.3 g, 24% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.65 (3 H, s), 4.19 (1 H, d, J = 14.2 Hz), 4.27 (1 H, d, J = 14.2 Hz), 5.82 (1 H, s), 7. 24-7.30 (1 H, m), 7.68-7. 72 (1 H, m), 8. 50-8. 53 (1 H, m), 8. 68 (1 H, d, J = 2.3 Hz ).

Example 621
Preparation of 2-Methyl-6-nitro-2- (pyridin-3-yl) -2,3-dihydroimidazo [2,1-b] oxazole 1- (2-chloro-4-nitro prepared according to example 620 2-Methyl pale brown powder crystal by the method of Example 544 using imidazol-1-yl) -2- (pyridin-3-yl) -propan-2-ol (3.3 g, 11.7 mmol) There was obtained -6-nitro-2- (pyridin-3-yl) -2,3-dihydroimidazo [2,1-b] oxazole (1.8 g, yield 63%).
Melting point 212-214 [deg.] C.

Example 622
Preparation of 2-Methyl-6-nitro-2- (1-oxypyridin-3-yl) -2,3-dihydroimidazo [2,1-b] oxazole 2-Methyl-6-nitro prepared in Example 621 -2- (Pyridin-3-yl) -2,3-dihydroimidazo [2,1-b] oxazole (800 mg, 3.3 mmol) and a mixture of methylene chloride (25 ml) under ice-cooling m- Chloroperbenzoic acid (1 g, 4.06 mmol) was added and stirred overnight at room temperature. The reaction solution was filtered, and the filtrate was washed successively with 20% aqueous sodium sulfite solution, saturated aqueous sodium bicarbonate solution and saturated brine, dried over magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure to give 2-methyl-6-nitro-2- (1-oxypyridin-3-yl) -2,3-dihydroimidazo [2,1-b] oxazole (white powder). 330 mg, 39%) were obtained.
¹ H-NMR (DMSO-d ₆ ) δ ppm:
1.92 (3 H, s), 4.51 (2 H, s), 7.42-7.53 (2 H, m), 8. 14 (1 H, s), 8.20-8.24 (1 H, 1 H, s) m), 8.42 (1 H, s).

Example 623
Preparation of 1- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperidin-4-one 1- (2-methyloxiranylmethyl) piperidine By the method of Example 597 using 4-one (2.2 g, 13 mmol), 1- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole as pale yellow powder -2-ylmethyl) piperidin-4-one (50 mg, 1% yield) was obtained.
Melting point 124-126 [deg.] C.

Example 624
Preparation of 4- [3- (2-Chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] -1- (4-trifluoromethylbenzyl) piperazin-2-one 4- (4- A slightly yellow powder is obtained according to the method of Example 541 using 2-methyl-2-oxiranylmethyl) -1- (4-trifluoromethylbenzyl) piperazin-2-one (1.6 g, 4.9 mmol) 4- [3- (2-Chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] -1- (4-trifluoromethylbenzyl) piperazin-2-one (1 g) The rate is 43%).
¹ H-NMR (CDCl ₃ ) δ ppm:
1.18 (3 H, s), 2. 45 (1 H, d, J = 13.9 Hz), 2.57 (1 H, d, J = 13.9 Hz), 2.72-2.98 (2 H, m) ), 3.19-3.44 (3 H, m), 3.55 (1 H, d, J = 16.5 Hz), 4.00 (1 H, d, J = 14.3 Hz), 4.10 (1 H) , D, J = 14.3 Hz), 4.64 (2 H, s), 7. 37 (2 H, d, J = 8.2 Hz), 7.61 (2 H, d, J = 8.2 Hz), 8 .02 (1 H, s).

  The compound of Example 625 was produced in the same manner as in Example 624, using the corresponding starting materials.

Example 625
1-tert-Butyl-4- [3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] piperazin-2-one
¹ H-NMR (CDCl ₃ ) δ ppm:
1.16 (3H, s), 1.44 (9H, s), 2.41 (1H, d, J = 13.8 Hz), 2.51 (1 H, d, J = 13.8 Hz), 65-2.88 (3H, m), 2.93-3.09 (1H, m), 3.12-3. 28 (2H, m), 3.99 (1H, d, J = 14.3 Hz ), 4.08 (1 H, d, J = 14.3 Hz), 8.05 (1 H, s).

Example 626
Preparation of 4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -1- (4-trifluoromethylbenzyl) piperazin-2-one 4- [3- (2-Chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] -1- (4-trifluoromethylbenzyl) piperazin-2-one (prepared in 624) By the method of Example 544 using 1 g (2.1 mmol), 4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl of slightly yellow powder )-(4-Trifluoromethylbenzyl) piperazin-2-one (206 mg, 22% yield) was obtained.
Mp 88-93 ° C.

  The compound of Example 627 was produced in the same manner as in Example 626, using the corresponding starting materials.

Example 627
1-tert-Butyl-4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-2-one melting point 193-194 ° C.

Example 628
Preparation of 1-tert-Butyl-4- [2- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-yl) ethyl] piperazin-2-one Methanesulfonic acid 2- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-yl) ethyl ester (290 mg, 1 mmol) prepared in 42, 1-tert hydrochloride -A mixture of butylpiperazin-2-one (200 mg, 1.28 mmol), triethylamine (242 mg, 2.39 mmol), potassium iodide (250 mg, 1.5 mmol) and DMF (3 ml) at 70 ° C. 4 Stir for hours. The reaction solution was cooled to room temperature, water was added, and the mixture was extracted twice with ethyl acetate. The organic phases were combined, washed twice with water, then washed with saturated brine, dried over magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (methylene chloride / methanol = 20/1) to give 1-tert-butyl-4- [2- (2-methyl-6-nitro-2) as a white powder. 27, 3-Dihydroimidazo [2,1-b] oxazol-2-yl) ethyl] piperazin-2-one (27 mg, 8% yield) was obtained.
Melting point 153-154 [deg.] C.

  The compound of Example 629 was produced in the same manner as Example 628 using the corresponding starting materials.

Example 629
4- [2- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-yl) ethyl] -1-phenylpiperazin-2-one melting point 199-202 (decomposition ).

Example 630
Preparation of 1-tert-Butyl-4- [3- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-yl) propyl] piperazin-2-one Using methanesulfonic acid 3- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-yl) propyl ester (300 mg, 0.98 mmol) prepared in 39, According to the method of Example 628, 1-tert-butyl-4- [3- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-yl) propyl as a white powder The piperazin-2-one (150 mg, 42% yield) was obtained.
Melting point 147-149 ° C (decomposition).

Example 631
Preparation of 1- (benzimidazol-1-yl) -3- (2-chloro-4-nitroimidazol-1-yl) -2-methylpropan-2-ol 1- (2-methyl-2-oxiranyl) By the method of Example 541, using methyl) -1H-benzimidazole (350 mg, 1.86 mmol), 1- (benzimidazol-1-yl) -3- (2-chloro-4-nitro) as white powder crystals. Imidazol-1-yl) -2-methylpropan-2-ol (135 mg, 22% yield) was obtained.
¹ H-NMR (DMSO-d ₆ ) δ ppm:
0.99 (3 H, s), 4.06 (1 H, d, J = 14.2 Hz), 4.23-4.45 (3 H, m), 5.44 (1 H, s), 7.14 7.32 (2 H, m), 7.57-7. 77 (2 H, m), 8. 15 (1 H, s), 8. 36 (1 H, s).

  The compound of Example 632 was produced in the same manner as in Example 631 using the corresponding starting materials.

Example 632
1- (Imidazol-1-yl) -3- (2-chloro-4-nitroimidazol-1-yl) -2-methylpropan-2-ol
¹ H-NMR (CDCl ₃ ) δ ppm:
1.19 (3 H, s), 3.86 to 4.05 (3 H, m), 4. 13 (1 H, d, J = 14.2 Hz), 6.87 (1 H, s), 6.89 (6 1 H, s), 7.47 (1 H, s), 8.08 (1 H, s).

Example 633
Preparation of 1- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -1H-benzimidazole 1- (benzimidazole-1 prepared in Example 631 -Yl) -3- (2-chloro-4-nitroimidazol-1-yl) -2-methylpropan-2-ol (135 mg, 0.4 mmol) according to the method of Example 544, white powder crystals The obtained 1- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -1H-benzimidazole (72 mg, yield 60%) was obtained.
Melting point 250.3-251.9 ° C (decomposition).

  The compound of Example 634 was produced in the same manner as in Example 633, using the corresponding starting materials.

Example 634
1- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) imidazole melting point 245.5-247.8 ° C.

Example 635
Preparation of (S) -1- (2-Chloro-4-nitroimidazol-1-yl) -3- (3,4-dihydro-2H-quinolin-1-yl) -2-methylpropan-2-ol (R) -2-Chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitroimidazole prepared in Example 12 (100 mg, 0.46 mmol), 1,2,3,4-tetrahydro A mixture of quinoline (122 mg, 0.92 mmol) and DMF (1 ml) was stirred at 80 ° C. for 8 hours. The reaction solution was cooled to room temperature, water was added, and the mixture was extracted twice with ethyl acetate. The organic phases were combined, washed twice with water, then washed with saturated brine, dried over magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (n-hexane / ethyl acetate = 1/1) to give (S) -1- (2-chloro-4-nitroimidazol-1-yl) as an orange oil. ) (3-Dichloro-2H-quinolin-1-yl) -2-methylpropan-2-ol (134 mg, 83% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.24 (3H, s), 1.94-2.04 (2H, m), 2.39 (1 H, m), 2.79-2.85 (2H, m), 3.27-3. 42 (4 H, m), 6.66-6.72 (2 H, m), 6.97-7.08 (2 H, m), 8.04 (1 H, s).

  The compounds of Example 636 to Example 638 shown in the following table were produced in the same manner as in Example 635, using the corresponding starting materials.

Example 639
Preparation of (S) -1- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -1,2,3,4-tetrahydroquinoline Example 635 S) -1- (2-Chloro-4-nitroimidazol-1-yl) -3- (3,4-dihydro-2H-quinolin-1-yl) -2-methylpropan-2-ol prepared in Using (134 mg, 0.38 mmol) and according to the method of Example 393, (S) -1- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole as a white powder -2-ylmethyl) -1,2,3,4-tetrahydroquinoline (64 mg, 54%) was obtained.
Melting point 168-172 [deg.] C.

  The compounds of Example 640 to Example 642 were produced in the same manner as in Example 639, using the corresponding starting materials.

Example 640
S) -2- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -1,2,3,4-tetrahydroisoquinoline melting point 153-155.3 ° C.

Example 641
(S) -2- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -2,3-dihydro-1H-isoindole
¹ H-NMR (CDCl ₃ ) δ ppm:
1.68 (3 H, s), 3.01 (1 H, d, J = 14.5 Hz), 3.24 (1 H, d, J = 14.5 Hz), 3.92 (1 H, d, J = 9) .6 Hz), 4.08 (4 H, s), 4.50 (1 H, d, J = 9.6 Hz), 7.13-7.21 (4 H, m), 7. 50 (1 H, s).

Example 642
(S) -8- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -1,4-dioxa-8-azaspiro [4,5] decane Mp 166.5-168.2 ° C.

Example 643
Preparation of (2S) -Methyl-6-nitro-2-[(2S)-(4-trifluoromethoxyphenoxymethyl) pyrrolidin-1-ylmethyl] -2,3-dihydroimidazo [2,1-b] oxazole (R) -2-Chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitroimidazole (645 mg, 2.97 mmol) prepared in Example 12; (S) -2- (4-) A mixture of trifluoromethoxyphenoxymethyl) pyrrolidine (930 mg, 3.56 mmol) and DMF (15 ml) was stirred at 80 ° C. for 8 hours. To the reaction mixture was added sodium hydride (154 mg, 3.86 mmol) under ice-cooling, and the mixture was stirred at the same temperature for 1 hour. The reaction solution was poured into ice water and extracted twice with ethyl acetate. The organic phases were combined, washed twice with water, then washed with saturated brine, dried over magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (methylene chloride), recrystallized from methylene chloride / isopropyl ether, and white powder of (2S) -methyl-6-nitro-2-[(2S)- (4-Trifluoromethoxyphenoxymethyl) pyrrolidin-1-ylmethyl] -2,3-dihydroimidazo [2,1-b] oxazole (505 mg, yield 41%) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.42-1.52 (1 H, m), 1.59 (3 H, s), 1.61-1. 79 (2 H, m), 1.87-1.99 (1 H, m), 50-2.61 (1 H, m), 3.03-3.17 (2 H, m), 3.06 (1 H, d, J = 14.7 Hz), 3.20 (1 H, d, J = 14) .7 Hz), 3.72-3.79 (2 H, m), 3.92 (1 H, dd, J = 9.2 Hz, 3.7 Hz), 4.58 (1 H, d, J = 9.5 Hz) , 6.80-6.88 (2H, m), 7.15-7. 19 (1 H, m), 7.42 (1 H, s).

Example 644
Preparation of 4- [3- (2-chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] homopiperazine-1-carboxylic acid tert-butyl ester 2-chloro-4-nitro- 1H-imidazole (8.39 g, 56.88 mmol), 4- (2-methyl-2-oxiranylmethyl) homopiperazine-1-carboxylic acid tert-butyl ester (15.38 g, 56.88 mmol) and A mixture of sodium acetate (5.13 g, 62.57 mmol) in 1-propanol (100 ml) was heated to reflux for 10 hours. The reaction solution was returned to room temperature and concentrated under reduced pressure. The residue was dissolved in methylene chloride, washed with water, dried over sodium sulfate and filtered. The filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 5/1) to give 4- [3- (2-chloro-4-nitroimidazole-1) as a reddish yellow oil. -Yl) -2-hydroxy-2-methylpropyl] homopiperazine-1-carboxylic acid tert-butyl ester (6.25 g, 27% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.14 (3 H, s), 1.48 (9 H, s), 1.69-1. 90 (2 H, m), 2.40-2.55 (1 H, m), 2. 66 (1 H, m) d, J = 14.1 Hz), 2.75-2.98 (5 H, m), 3.30-3.59 (4 H, m), 3.96 (2 H, s), 8.06 (1 H, 1 H, m) s).

Example 645
Preparation of 4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) homopiperazine-1-carboxylic acid tert-butyl ester Prepared in Example 644 4 -[3- (2-Chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] homopiperazine-1-carboxylic acid tert-butyl ester (6.25 g, 14.96 mmol) By the method of Example 544, 4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) homopiperazine-1-carboxylic acid tert of white powder is used. -Butyl ester (3.07 g, 54% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.47 (9H, s), 1.59 (3H, s), 1.68-1.79 (2H, m), 2.63-2.90 (5H, m), 3.06 (1H, 1H, s) d, J = 15.1 Hz), 3.25-3.50 (4 H, m), 3.91 (1 H, d, J = 9.7 Hz), 4.33 (1 H, d, J = 9.7 Hz) ), 7.54 (1 H, s).

Example 646
Preparation of 4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) homopiperazine-1-carboxylic acid benzyl ester hydrochloride Prepared as in Example 645 4 -(2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) homopiperazine-1-carboxylic acid tert-butyl ester (250 mg, 0.655 mmol) and tri- The mixture of fluoroacetic acid (10 ml) was stirred overnight at room temperature. The reaction solution is concentrated under reduced pressure, the residue is dissolved in 10 ml of methylene chloride, triethylamine (0.27 ml, 1.96 mmol) is added, and then benzyl chloroformate (0.19 ml, 1.31 mmol) is added. The mixture was stirred at room temperature for 3 hours. Water was added to the reaction solution, extracted with methylene chloride, dried over magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride / ethyl acetate = 1/1) to give a slightly yellow oil. The resulting oil is dissolved in ethyl acetate, and crystals obtained by adding saturated hydrochloric acid / ethyl acetate solution are collected by filtration to give 4- (2-methyl-6-nitro-2,3-dihydroimidazo) as white powder crystals. [2,1-b] oxazol-2-ylmethyl) homopiperazine-1-carboxylic acid benzyl ester hydrochloride (246 mg, 83% yield) was obtained.
115-117 ° C.

Example 647
Preparation of 2- [4- (4-Biphenylylmethyl) homopiperazin-1-ylmethyl] -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole Prepared as in Example 645 4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) homopiperazine-1-carboxylic acid tert-butyl ester (346 mg, 0.91 mmol) and The mixture of trifluoroacetic acid (10 ml) was stirred overnight at room temperature. The reaction solution was concentrated under reduced pressure, the residue was dissolved in 10 ml of methylene chloride, and triethylamine (0.27 ml, 1.96 mmol) was added. Concentrate under reduced pressure and dissolve the residue in 10 ml of methanol. To this solution, 4-phenylbenzaldehyde (496 mg, 2.72 mmol), sodium cyanoborohydride (171 mg, 2.72 mmol), acetic acid (0.17 ml, 2.72 mmol) are added in this order, and the solution is cooled to room temperature. Stir overnight. The reaction solution was poured into a saturated aqueous solution of sodium hydrogen carbonate, extracted with methylene chloride, dried over magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 5/1) to give 2- [4- (4-biphenylylmethyl) homopiperazine-1 as a colorless powder. Ylmethyl] -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole (251 mg, 62% yield) was obtained.
Melting point 138-142.2 [deg.] C.

Example 648
Preparation of 1′-tert-butoxycarbonyl-2,3-dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4′-piperidine] 2,4-dinitro-1H-imidazole (1 .0 g, 6.3 mmol), 1-oxa-6-aza-spiro [2,5] octane-6-carboxylic acid tert-butyl ester (2.0 g, 9.5 mmol) and sodium acetate (612 mg, 7 .5 mmol) was heated to reflux for 10 hours in ethanol (7 ml). The reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate solution and methylene chloride were added, and the mixture was vigorously stirred. The reaction solution was extracted with methylene chloride, dried over sodium sulfate and filtered. The resulting filtrate is concentrated under reduced pressure, and the residue is crystallized with methylene chloride-diisopropyl ether to give 1′-tert-butoxycarbonyl-2,3-dihydro-6-nitro-spiro [imidazo [2, 1-b] oxazole-2,4'-piperidine] (586 mg, 29% yield) was obtained.
Melting point 230-232 [deg.] C.

Example 649
Preparation of 4- (2-Chloro-4-nitroimidazol-1-ylmethyl) -4-hydroxypiperidine-1-carboxylic acid tert-butyl ester 2-Chloro-4-nitro-1H-imidazole (3.1 g, 21. 0 mmol), 1-oxa-6-aza-spiro [2,5] octane-6-carboxylic acid tert-butyl ester (4.4 g, 21.0 mmol) and sodium hydrogen carbonate (1.94 g, 23.1. The mmol) was heated to reflux for 6 hours in ethanol (20 ml). The reaction mixture was concentrated under reduced pressure, water was added, and the mixture was extracted with methylene chloride, dried over magnesium sulfate and filtered. The obtained filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (methylene chloride / methanol = 100/1) to give 4- (2-chloro-4-nitroimidazole-1-) as a yellow oily substance. Ylmethyl) -4-hydroxypiperidine-1-carboxylic acid tert-butyl ester (5.4 g, 72% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.45-1.71 (5H, m), 1.46 (9H, s), 3.03-3.14 (2H, m), 3.90-4.03 (2H, m), 4.. 02 (2H, s), 7.91 (1 H, s).

Example 650
Preparation of 4- {2- [4- (2-chloro-4-nitroimidazol-1-ylmethyl) -4-hydroxypiperidin-1-yl] -2-oxoethyl} piperazine-1-carboxylic acid tert-butyl ester 2 -Chloro-4-nitro-1H-imidazole (1.29 g, 8.76 mmol), 4- {2- (1-oxa-6-azaspiro [2,5] octan-6-yl) -2-oxoethyl} Piperazine-1-carboxylic acid tert-butyl ester (2.97 g, 8.76 mmol) and sodium hydrogen carbonate (809 mg, 9.64 mmol) were heated to reflux for 5 hours in ethanol (10 ml). The reaction mixture was concentrated under reduced pressure, a saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with methylene chloride, dried over magnesium sulfate and filtered. The obtained filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (methylene chloride / methanol = 100/1) to give a yellow oily substance 4- {2- [4- (2-chloro-4) -Nitroimidazol-1-ylmethyl) -4-hydroxypiperidin-1-yl] -2-oxoethyl} piperazine-1-carboxylic acid tert-butyl ester (2.58 g, yield 61%) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.45 (9 H, s), 1.53-1.71 (4 H, m), 2.44 (4 H, br), 2.96-3.04 (1 H, m), 3.10-3. 27 (2H, m), 3.35-3.48 (4H, m), 3.90-3.96 (2H, m), 4.05 (2H, s), 4.32-4.37 ( 2H, m), 8.04 (1 H, s).

  The compound of Example 651 was produced in the same manner as Example 650 using 6- (4-trifluoromethylphenyl) -1-oxa-6-aza-spiro [2,5] octane.

Example 651
4- (2-Chloro-4-nitroimidazol-1-ylmethyl) -1- (4-trifluoromethylphenyl) piperidin-4-ol pale pink powder, yield 54%
¹ H-NMR (CDCl ₃ ) δ ppm:
1.60-1.66 (2H, m), 1.82-1.93 (3H, m), 3.10-3.22 (2H, m), 3.62-3.67 (2H, m) ), 4.07 (2H, s), 6.95 (2H, d, J = 8.7 Hz), 7.50 (2 H, d, J = 8.7 Hz), 7.99 (1 H, s).

Example 652
Preparation of 1′-tert-Butoxycarbonyl-2,3-dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4′-piperidine] (another synthetic method of the compound of Example 648)
4- (2-chloro-4-nitroimidazol-1-ylmethyl) -4-hydroxypiperidine-1-carboxylic acid tert-butyl ester (26.7 g, 74.0 mmol) prepared in Example 649 was 1,4 Dissolve in dioxane (200 ml). To this solution was added sodium hydride (3.6 g, 88.8 mmol) under ice-cooling, and the mixture was heated to reflux for 8 hours. The reaction mixture was concentrated under reduced pressure, ice water and methylene chloride were added to the residue, and the mixture was vigorously stirred. The precipitate was collected by filtration, washed with water and methanol, and dried under reduced pressure to obtain 16.4 g of primary crystals. Furthermore, the previous filtrate is extracted with methylene chloride and dried over magnesium sulfate, and the filtrate obtained by filtration is concentrated under reduced pressure, methanol is added to the residue, and crystallization is performed to give 2.7 g of secondary crystals. I got The primary and secondary crystals are combined to give 1'-tert-butoxycarbonyl-2,3-dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine] as a white powder. (19.1 g, yield 79%) was obtained.
Melting point 230-232 [deg.] C.

Example 653
4- [2- (2,3-dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine] -1'-yl) -2-oxoethyl] piperazine-1 Preparation of Carboxylic Acid tert-Butyl Ester 4- {2- [4- (2-Chloro-4-nitroimidazol-1-ylmethyl) -4-hydroxypiperidin-1-yl] -2-oxoethyl prepared according to Example 650 } Piperazine carboxylic acid tert-butyl ester (2.58 g, 5.3 mmol) was dissolved in dioxane (30 ml). To this solution was added sodium hydride (254 mg, 6.36 mmol) under ice-cooling, and the mixture was heated to reflux overnight. The reaction mixture was concentrated under reduced pressure, ice water and ethyl acetate were added to the residue, and the mixture was vigorously stirred. The precipitate is collected by filtration, washed with water and ethyl acetate, and dried under reduced pressure to give 4- [2- (2,3-dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-] as a white powder. 2,4'-Piperidine] -1'-yl) -2-oxoethyl] piperazine-1-carboxylic acid tert-butyl ester (996 mg, 42% yield) was obtained.
Mp 211.0-213.0 ° C.

  The compound of Example 654 was produced in the same manner as Example 653 using the corresponding starting materials.

Example 654
2,3-Dihydro-6-nitro-1 '-(4-trifluoromethylphenyl) -spiro [imidazo [2,1-b] oxazole-2,4'-piperidine]
White powder, 79% yield
MS; 368 (M ⁺ )
Mp 249.2-250.1 ° C.

Working Example 655
Preparation of 2,3-Dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4′-piperidine] · trifluoroacetate salt 1′-tert-butoxycarbonyl prepared according to example 652 2,3-Dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine] (42 g, 0.13 mol) is suspended in methylene chloride (100 ml) and cooled with ice. Trifluoroacetic acid (60 ml) was added dropwise and stirred at room temperature overnight. The reaction solution was concentrated under reduced pressure and methanol was added to crystallize. The resultant is collected by filtration, washed with methanol and ethyl acetate, dried under reduced pressure, and 2,3-dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine as light brown powder. ] · Trifluoroacetic acid salt (43.6 g, yield 99%) was obtained.
MS 224 (M ⁺ )
Melting point 196-198 ° C (decomposition)
¹ H-NMR (DMSO-d ₆ ) δ ppm:
2.06-2.32 (4H, m), 3.12-3. 35 (4H, m), 4.24 (2H, s), 8.21 (1 H, s), 8.88 (2H, 2) bs).

Example 656
Preparation of 1′-Acetyl-2,3-dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4′-piperidine] 2,3-dihydro-6- manufactured according to example 655 Nitro-spiro [imidazo [2,1-b] oxazole-2,4-piperidine] trifluoroacetate (85.5 mg, 0.25 mmol) is suspended in methylene chloride (5 ml), triethylamine (74 μl) and acetyl Chloride (20 μl) was added and stirred for 1 hour at room temperature. The reaction solution was concentrated under reduced pressure, methanol and water were added to the residue, and the mixture was vigorously stirred. The precipitate is collected by filtration, washed with water and isopropyl ether, and then dried under reduced pressure to obtain 1′-acetyl-2,3-dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole as a white powder. -2,4'-piperidine] (37.8 mg, yield 56%) was obtained.
MS: 266 (M ⁺ )
Mp 232.0-234.0 ° C.

Example 657
Preparation of 1 ′-(4-Trifluoromethylphenylacetyl) -2,3-dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4′-piperidine] Prepared as in Example 655 2,3-Dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine] trifluoroacetate (300 mg, 0.89 mmol) was suspended in methylene chloride (5 ml) Triethylamine (0.4 ml, 2.66 mmol) and (.alpha.,. Alpha.,. Alpha .-. Alpha.-trifluoro-p-tolyl) acetic acid chloride (2.7 ml, 1.33 mmol) were added and stirred for 1 hour at room temperature. The reaction solution was poured into saturated aqueous sodium hydrogen carbonate solution, extracted with methylene chloride, dried over magnesium sulfate and filtered. The obtained filtrate is concentrated under reduced pressure, and the residue is separated and purified by silica gel column chromatography (methylene chloride / methanol = 200/1), crystallized from methylene chloride-isopropyl ether, collected by filtration, and dried under reduced pressure To give 1 ′-(4-trifluoromethylphenylacetyl) -2,3-dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4′-piperidine] (white powder). 143 mg (yield 39%) were obtained.
MS: 410 (M ⁺ )
Mp 185.0-187.0 ° C.

Example 658
Preparation of 1 ′-(3,4-Dichlorophenoxyacetyl) -2,3-dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4′-piperidine] Prepared in Example 655 2,3-Dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine] trifluoroacetic acid salt (300 mg, 0.89 mmol), (3,4-dichlorophenyl) acetic acid (294 mg, 1.24 mmol) and WSCD (255 mg, 1.24 mmol) were stirred in DMF (5 ml) at room temperature for 1.5 hours. Water and diethyl ether were added to the reaction solution, and the mixture was vigorously stirred. The precipitate is collected by filtration, washed with water and diethyl ether, dried under reduced pressure, and white powder of 1 ′-(3,4-dichlorophenoxyacetyl) -2,3-dihydro-6-nitro-spiro [imidazo [2]. , 1-b] oxazole-2,4'-piperidine] (96 mg, 25% yield) was obtained.
Mp 218.0-220.0 ° C.

Example 659
Preparation of 2,3-Dihydro-1'-methyl-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine] 2,3-dihydro-6- manufactured according to example 655 2,3-Dihydro-6-nitro-spiro [imidazo [2,1-b] obtained by freeing nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine] trifluoroacetate salt ] Oxazole-2,4'-piperidine] (250 mg, 1.12 mmol) was suspended in methanol (5 ml). To this suspension is added 37% formaldehyde solution (0.25 ml, 3.35 mmol), sodium cyanoborohydride (210 mg, 3.35 mmol) and acetic acid (0.19 ml, 3.35 mmol), Stir at room temperature for 3 hours. The reaction mixture was poured into saturated aqueous sodium hydrogen carbonate solution and extracted with methylene chloride. The organic phase was dried over sodium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue is crystallized from methylene chloride-diisopropyl ether and white powder of 2,3-dihydro-1'-methyl-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine] (160 mg) , Yield 60%).
MS: 238 (M ⁺ )
Melting point 237.0-239.0 ° C (decomposition).

Example 660
Preparation of 1′-Benzenesulfonyl-2,3-dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4′-piperidine] 2,3-Dihydro-6 prepared in Example 655 -Nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine] trifluoroacetate (197 mg, 0.88 mmol) was suspended in methylene chloride (5 ml), triethylamine (0.36 ml, 2.64 mmol) and benzenesulfonyl chloride (0.28 ml, 2.10 mmol) were added and stirred at room temperature for 30 minutes. Diisopropyl ether and water were added to the reaction solution, and the mixture was vigorously stirred. The precipitate is collected by filtration, washed with water and diisopropyl ether and then dried under reduced pressure to obtain 1′-benzenesulfonyl-2,3-dihydro-6-nitro-spiro [imidazo [2,1-b] as a white powder. Oxazole-2,4'-piperidine] (210 mg, 66% yield) was obtained.
MS: 364 (M ⁺ )
¹ H-NMR (DMSO-d ₆ ) δ ppm:
1.99-2.18 (4 H, m), 2.49-2.63 (2 H, m), 3. 40-3.54 (2 H, m), 4. 10 (2 H, s), 7. 65-7.81 (5 H, m), 8.21 (1 H, s).

  The compound of Example 661 is produced in the same manner as in Example 660 using the corresponding starting materials.

Working Example 661
1′-methanesulfonyl-2,3-dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4′-piperidine]
¹ H-NMR (DMSO-d ₆ ) δ ppm:
1.98-2.22 (4H, m), 2.94 (3H, s), 3.04-3.13 (2H, m), 3.43-3.51 (2H, m), 4. 16 (2 H, s), 8. 17 (1 H, s).

Example 662
Preparation of 1′-Benzyloxycarbonyl-2,3-dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4′-piperidine] 2,3-dihydro- prepared according to example 655 6-Nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine] trifluoroacetate (250 mg, 0.74 mmol) was suspended in methylene chloride (5 ml) and triethylamine (0.40 ml) , 2.96 mmol) and benzyl chloroformate (0.32 ml, 2.22 mmol) were added and stirred at room temperature for 30 minutes. The reaction solution is concentrated under reduced pressure, and the residue is separated and purified by silica gel column chromatography (methylene chloride / methanol = 200/1), crystallized from methylene chloride-isopropyl ether, collected by filtration, and dried under reduced pressure. The white powder of 1′-benzyloxycarbonyl-2,3-dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4′-piperidine] (224 mg, yield 84%) Obtained.
Melting point 175.0-177.0 ° C.

Working Example 663
Preparation of 1 ′-(4-Trifluoromethylbenzyloxycarbonyl) -2,3-dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4′-piperidine] Preparation in Example 655 Suspended 2,3-dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine] trifluoroacetate (33 g, 97.6 mmol) in DMF (200 ml) Then, triethylamine (20 ml, 0.15 mol) was added and stirred. There, 4-trifluoromethylbenzyl alcohol (25.8 g, 0.15 mol) and 1,1'-carbonyldiimidazole (23.7 g, 0.15 mol) are dissolved in DMF (100 m), and room temperature is maintained for 3 hours. The stirred mixture was added and stirred at 70 ° C. for 2 hours. The reaction solution was evaporated under reduced pressure, water was added to the residue, and the precipitate was collected by filtration. This is separated and purified by silica gel column chromatography (methylene chloride / ethyl acetate = 10/1), recrystallized from ethyl acetate-isopropyl ether, filtered and dried under reduced pressure to obtain a white powder 1 ′-(1 4-trifluoromethylbenzyloxycarbonyl) -2,3-dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine] (37.2 g, yield 90%) Obtained.
Melting point 189-190 [deg.] C.

  The compounds of Example 664 and Example 665 were produced in the same manner as in Example 663, using the corresponding starting materials.

Working Example 664
1 '-[(4-Trifluoromethoxy) benzyloxycarbonyl] -2,3-dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine]
¹ H-NMR (CDCl ₃ ) δ ppm:
1.80 to 1.93 (2H, m), 2.13 to 2.19 (2H, m), 3.32 to 3.42 (2H, m), 4.00 to 4.20 (2H, m) ), 4.03 (2H, s), 5.14 (2H, s), 7.20-7.23 (2H, m), 7.38-7.46 (2H, m), 7.54 ( 1 H, s).

Example 665
1 ′-(4-formylaminobenzyloxycarbonyl) -2,3-dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4′-piperidine]
¹ H-NMR (DMSO-d ₆ ) δ ppm:
1.85-2.10 (4H, m), 3.15-3.40 (2H, m), 3.65-3.85 (2H, m), 4.16 (2H, s), 5. 03 (2 H, s), 7.33 (2 H, d, J = 8.5 Hz), 7.58 (2 H, d, J = 8.5 Hz), 8. 15 (1 H, s), 8. 27 ( 1 H, s).

Example 667
Preparation of 2,3-Dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine] -1'-carboxylic acid phenylamide The 2,3-dihydro prepared according to example 655 -6-Nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine] trifluoroacetate (100 mg, 0.30 mmol) is suspended in 5 ml DMF, triethylamine (43 μl, 0.31 mmol) ) And phenyl isocyanate (34 μl, 0.31 mmol) were added and stirred at room temperature for 30 minutes. Water was added to the reaction solution and the mixture was stirred, and the precipitate was collected by filtration. This is separated and purified by silica gel column chromatography (methylene chloride / methanol = 100/1), recrystallized from ethyl acetate, filtered and dried under reduced pressure to give 2,3-dihydro-6-nitro as a white powder. -Spiro [imidazo [2,1-b] oxazole-2,4'-piperidine] -1'-carboxylic acid phenylamide (90 mg, yield 88%) was obtained.
MS; 343 (M ⁺ )
Melting point 229-232 ° C (decomposition).

  The compounds of Example 668 and Example 669 were prepared in the same manner as Example 667 using 4-isocyanate pyridine or benzyl isocyanate.

Example 668
2,3-Dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine] -1'-carboxylic acid 4-pyridine amide melting point 217-219 [deg.] C.

Working Example 669
2,3-Dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine] -1'-carboxylic acid benzylamide mp 244-247 ° C (decomp.).

Example 670
4- (2,3-Dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine] -1'-ylcarbonyl) piperazine-1-carboxylic acid tert-butyl ester Preparation Triphosgene (227 mg, 0.77 mmol) was dissolved in 10 ml of toluene and ice cooled. To this solution was added piperazine-1-carboxylic acid tert-butyl ester (425 mg, 2.28 mmol) and diisopropylethylamine (0.4 ml, 2.28 mmol) and stirred for 1 hour, following in Example 655. The prepared 2,3-dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine] trifluoroacetate (700 mg, 2.07 mmol) is added, and it is kept for 1 hour at room temperature. Stir and heat at reflux for an additional hour. The reaction solution was poured into water and extracted with ethyl acetate. The organic phase was washed with brine, dried over magnesium sulfate and filtered. The obtained filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (methylene chloride / acetone = 10/1) and then crystallized from methylene chloride-diisopropyl ether to give a white powder 4- (2 , 3-Dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine] -1'-ylcarbonyl) piperazine-1-carboxylic acid tert-butyl ester (342 mg, yield 38%).
Melting point 260.0-265.0 ° C (decomposition)
¹ H-NMR (CDCl ₃ ) δ ppm:
1.47 (9 H, s), 1.90-2.02 (2 H, m), 2.10-2.16 (2 H, m), 3.23-3.47 (10 H, m), 3. 60-3.66 (2H, m), 3.96 (2H, s), 7.54 (1 H, s).

  The compounds of Example 671 to Example 672 were prepared in the same manner as in Example 670, using piperazine-1-carboxylic acid 4-trifluoromethylbenzyl ester or 1- (4-trifluoromethylbenzyl) piperazine.

Example 671
4- (2,3-Dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine] -1'-ylcarbonyl) piperazine-1-carboxylic acid 4-trifluoromethyl Benzylic ester mp 221-223 ° C.

Working Example 672
1- (2,3-dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine] -1'-ylcarbonyl) -4- (4-trifluoromethylbenzyl) Piperazine melting point 226-230 ° C (decomposition).

Example 673
Preparation of 2,3-Dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine] -1'-carboxylic acid 4- (dimethylamino) phenylamide Prepared as in Example 655 Suspended 2,3-dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine] trifluoroacetate (200 mg, 0.59 mmol) in DMF (5 ml) Then, triethylamine (0.1 ml, 0.72 mmol) was added and stirred. Dissolve N, N-dimethyl-p-phenylenediamine (132 mg, 0.98 mmol) and 1,1'-carbonyldiimidazole (82.7 mg, 1.02 mmol) in DMF (5 ml) for 3 hours at room temperature The stirred mixture was added and stirred at room temperature for 30 minutes. Water was added to the reaction solution, the mixture was stirred, and the precipitate was collected by filtration. The product is separated and purified by silica gel column chromatography (methylene chloride / methanol = 100/1), crystallized from ethyl acetate, filtered and dried under reduced pressure to obtain 2,3-dihydro-6- of a white powder. Nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine] -1'-carboxylic acid 4- (dimethylamino) phenylamide (181 mg, yield 79%) was obtained.
MS 386 (M ⁺ )
Melting point 244-247 [deg.] C (decomposition).

  The compounds of Example 674 and Example 675 were prepared in the same manner as in Example 673, using 4-trifluoromethylbenzylamine or 4-trifluoromethoxybenzylamine.

Working Example 674
2,3-Dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine] -1'-carboxylic acid 4-trifluoromethylbenzylamide melting point 215-217 [deg.] C.

Example 675
2,3-dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine] -1'-carboxylic acid 4-trifluoromethoxybenzylamide melting point 223-225 [deg.] C.

Example 676
Preparation of 2,3-Dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine] -1'-carbothioic acid 4-chlorophenylamide Prepared according to example 655 2,3 -Dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine] trifluoroacetate (200 mg, 0.59 mmol) was suspended in DMF (5 ml), triethylamine (0%) .24 ml, 1.77 mmol) and 4-chlorophenyl isothiocyanate (200 mg, 1.18 mmol) were added and stirred at room temperature for 30 minutes. Water was added to the reaction solution and the mixture was stirred, and the precipitate was collected by filtration. The product is separated and purified by silica gel column chromatography (methylene chloride / methanol = 100/1), crystallized with methylene chloride-diisopropyl ether, filtered and dried under reduced pressure to obtain 2,3-dihydro of white powder. -6-Nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine] -1'-thiocarboxylic acid 4-chlorophenylamide (222 mg, yield 87%) was obtained.
¹ H-NMR (DMSO-d ₆ ) δ ppm:
2.02-2.19 (4H, m), 3.59-3.69 (2H, m), 4.19 (2H, s), 4.40-4.54 (2H, m), 7.. 30-7.37 (4 H, m), 8. 18 (1 H, s), 9. 48 (1 H, s).

Example 677
Preparation of 4-[(2,3-dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine])-1'-ylcarbonyl] aminobenzoic acid 4-[( 2,3-Dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine])-1'-ylcarbonyl] aminobenzoic acid tert-butyl ester (150 mg, 0.68 The mmol) was dissolved in methylene chloride (1 ml), trifluoroacetic acid (5 ml) was added and stirred overnight at room temperature. The reaction solution is concentrated under reduced pressure, and methanol-ethyl acetate is added to the residue for crystallization to give 4-[(2,3-dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole as a white powder. -2,4'-Piperidine])-1'-ylcarbonyl] aminobenzoic acid (59 mg, 45% yield) was obtained.
Melting point> 300 ° C
¹ H-NMR (DMSO-d ₆ ) δ ppm:
1.92-2.12 (4H, m), 3.32-3.39 (2H, m), 3.86-3.95 (2H, m), 4.17 (2H, s), 7.. 45 (2H, d, J = 8.8 Hz), 7.82 (2 H, d, J = 8.8 Hz), 8.17 (1 H, s), 8.97 (1 H, s), 12.54 ( 1 H, s).

Example 678
Preparation of 2-[(2,3-Dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine])-1'-yl] benzothiazole Prepared as in Example 655 2,3-Dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine] trifluoroacetic acid salt (84 mg, 0.25 mmol) is suspended in DMF (3 ml), Triethylamine (76 μl, 0.55 mmol) and 2-chlorobenzthiazole (40 μl, 0.30 mmol) were added and stirred at 80 ° C. for 1 hour. The reaction solution was evaporated under reduced pressure, water was added to the residue, and the precipitate was collected by filtration. This is crystallized with methylene chloride-methanol, collected by filtration, and dried under reduced pressure to give 2-[(2,3-dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-] as a white powder. 2,4'-Piperidine])-1'-yl] benzothiazole (55 mg, 62% yield) was obtained.
MS; 357 (M ⁺ )
¹ H-NMR (DMSO-d ₆ ) δ ppm:
2.05-2.23 (4H, m), 3.52-3.63 (2H, m), 3.89-3.97 (2H, m), 4.18 (2H, s), 7. 05-7.12 (1 H, m), 7.26-7.32 (1 H, m), 7.46-7.49 (1 H, m), 7.76-7.80 (1 H, m), 8.18 (1 H, s).

  The compound of Example 679 was produced in the same manner as Example 678 using 5-chloro-1-phenyl-1H-tetrazole.

Example 679
5-[(2,3-dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine])-1'-yl} -1-phenyl-1H-tetrazole
¹ H-NMR (DMSO-d ₆ ) δ ppm:
2.05 to 2.09 (4H, m), 3.24 to 3.40 (4H, m), 4.14 (2H, s), 7.59 to 7.72 (5H, m), 8. 15 (1 H, s).

Example 680
Preparation of 4- (2,3-Dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine] -1'-ylacetyl) piperazine-1-carboxylic acid tert-butyl ester 2,3-Dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine] trifluoroacetate (700 mg, 2.07 mmol) prepared in Example 655 in 20 ml DMF Suspended, 4- (chloroacetyl) piperazine-1-carboxylic acid tert-butyl ester (599 mg, 2.28 mmol), diisopropylethylamine (0.8 ml, 4.57 mmol) and sodium iodide (310 mg, 2.07) Add millimoles) and stir at 100 ° C. for 3 hours. The reaction solution was allowed to cool to room temperature, ethyl acetate and water were added, and the mixture was vigorously stirred. The precipitate is collected by filtration, washed with water and ethyl acetate, and dried under reduced pressure to give 4- (2,3-dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2 as a white powder. 4,4'-Piperidine] -1'-ylacetyl) piperazine-1-carboxylic acid tert-butyl ester (688 mg, 74% yield) was obtained.
Melting point> 300 ° C
¹ H-NMR (DMSO-d ₆ ) δ ppm:
1.41 (9 H, s), 1.95 to 2.01 (4 H, m), 2.43 to 2.64 (4 H, m), 3.21 (2 H, s), 3.26-3. 42 (6 H, m), 3.50-3.52 (2 H, m), 4.12 (2 H, s), 8. 14 (1 H, s).

  Examples 681 and Examples 268, using 2-chloro-N- (4-trifluoromethylphenyl) acetamide or 3- (3-chloropropyl) -3H-benzoxazol-2-one, analogous to example 680 682 compounds were produced.

Example 681
(2,3-Dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine])-1'-ylacetic acid (4-trifluoromethylphenyl) amide melting point 273-275 ° C (decomposition).

Example 682
3- [3- (2,3-Dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine])-1'-yl] propyl-3H-benzoxazole-2 -Melting point 190-192 [deg.] C.

Example 683
4- [2- (2,3-Dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine])-1'-ylethyl] piperazine-1-carboxylic acid tert- Preparation of butyl ester 2,3-Dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4′-piperidine] trifluoroacetate prepared in Example 655 (200 mg, 0.59 mmol ) Was suspended in 5 ml DMF, 4- (2-chloroethyl) piperazine-1-carboxylic acid tert-butyl ester (150 mg, 0.60 mmol), triethylamine (0.25 ml, 1.79 mmol) and sodium iodide (108 mg) , 0.72 mmol) was added and stirred at 50 ° C. for 5 hours. The reaction solution was allowed to cool to room temperature, ethyl acetate and water were added, and the mixture was vigorously stirred. The precipitate is collected by filtration, washed with water and ethyl acetate, and dried under reduced pressure to give 4- [2- (2,3-dihydro-6-nitro-spiro [imidazo [2,1-b] as a white powder. Oxazole-2,4′-piperidine])-1′-ylethyl] piperazine-1-carboxylic acid tert-butyl ester (80 mg, 31% yield) was obtained.
Melting point 214-215 [deg.] C.

Example 684
4- [2- (2,3-dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine] -1'-yl) -2-oxoethyl] piperazine-1 Preparation of carboxylic acid 4-trifluoromethylbenzyl ester 4- [2- (2,3-dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-) prepared in Example 653 Dissolve piperidine] -1'-yl) -2-oxoethyl] piperazine-1-carboxylic acid tert-butyl ester (300 mg, 0.67 mmol) in 5 ml of methylene chloride, add 5 ml of trifluoroacetic acid and stir at room temperature for 6 hours It stirred. The reaction solution was concentrated under reduced pressure, and 1 ml each of methylene chloride and triethylamine were added. The reaction solution was stirred at room temperature for 5 minutes, concentrated under reduced pressure, and the residue was dissolved in 15 ml of DMF. Thereto, a mixture of 4-trifluoromethylbenzyl alcohol (293 mg, 1.67 mmol) and 1,1'-carbonyldiimidazole (270 mg, 1.67 mmol) dissolved in 5 ml of DMF and stirred at room temperature for 3 hours is added, and room temperature is added. Stir overnight. The reaction mixture was poured into water, extracted with ethyl acetate, and the organic phase was washed with saturated brine. The mixture was dried over magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue is separated and purified by silica gel column chromatography (methylene chloride / methanol = 200/1), crystallized from methylene chloride-isopropyl ether, filtered and dried under reduced pressure to obtain 4- [2 of slightly pink powder -(2,3-dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine] -1'-yl) -2-oxoethyl] piperazine-1-carboxylic acid 4- Trifluoromethyl benzyl ester (324 mg, 88% yield) was obtained.
MS 553 (M + H) ⁺
Melting point 139.0-141.0 ° C.

  The compound of Example 685 was produced in the same manner as in Example 684, using the corresponding starting materials.

Working Example 685
4- [2- (2,3-dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine] -1'-yl) -2-oxoethyl] piperazine-1 Carboxylic acid 4-trifluoromethoxybenzyl ester mp 137-139 ° C.

  4- [2- (2,3-Dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine])-1'-ylethyl] piperazine prepared in Example 683 The compounds of Example 686 to Example 689 were produced in the same manner as Example 684 using 1-carboxylic acid tert-butyl ester.

Example 686
4- [2- (2,3-Dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine])-1'-ylethyl] piperazine-1-carboxylic acid 4- Chlorobenzyl ester mp 178-179 ° C.

Example 687
4- [2- (2,3-Dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine])-1'-ylethyl] piperazine-1-carboxylic acid 4- Trifluoromethyl benzyl ester mp 174-175 ° C.

Example 688
4- [2- (2,3-Dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine])-1'-ylethyl] piperazine-1-carboxylic acid 4- Trifluoromethoxybenzyl ester mp 176-177 ° C.

Example 689
4- [2- (2,3-Dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine])-1'-ylethyl] piperazine-1-carboxylic acid 4- Biphenylyl methyl ester
¹ H-NMR (CDCl ₃ ) δ ppm:
1.90-2.05 (2H, m), 2.15-2.20 (2H, m), 2.40-2.80 (12H, m), 3.45-3.60 (4H, m) ), 3.99 (2H, s), 5.17 (2H, s), 7.31-7.62 (10H, m).

  4- (2,3-Dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine] -1'-ylacetyl) piperazine-1-carboxylic acid prepared in Example 680 The compound of Example 690 was produced in the same manner as in Example 684, using tert-butyl ester.

Example 690
4- (2,3-Dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine] -1'-ylacetyl) piperazine-1-carboxylic acid 4- (trifluoromethyl) ) Benzyl ester mp 137-139 ° C.

Example 691
1- (2,3-dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine] -1'-yl) -2- [4- (4-trifluoromethyl) Preparation of benzyl) piperazin-1-yl] ethanone The 4- [2- (2,3-dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4′- prepared in Example 653 Dissolve piperidine] -1'-yl) -2-oxoethyl] piperazine-1-carboxylic acid tert-butyl ester (300 mg, 0.67 mmol) in 5 ml of methylene chloride, add 10 ml of trifluoroacetic acid and stir at room temperature for 6 hours It stirred. The reaction solution was concentrated under reduced pressure, and 1 ml each of methylene chloride and triethylamine were added. After stirring for 5 minutes at room temperature, the solution was concentrated under reduced pressure. The residue is dissolved in 10 ml of methanol and 4-trifluoromethylbenzaldehyde (0.23 ml, 1.67 mmol), sodium cyanotrihydroborate (105 mg, 1.67 mmol) and 0.1 ml of acetic acid are added under ice cooling. The temperature was raised to room temperature and stirred overnight. To this was then added saturated aqueous sodium hydrogen carbonate solution and methylene chloride and stirred. The organic phase was dried over magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue is separated and purified by silica gel column chromatography (methylene chloride / methanol = 50/1), crystallized from methylene chloride-diisopropyl ether, filtered and dried under reduced pressure to obtain a white powder of 1- (2, 3 -Dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine] -1'-yl) -2- [4- (4-trifluoromethylbenzyl) piperazine-1-] [EI] ethanone (226 mg, 67% yield) was obtained.
MS: 508 (M ⁺ )
Melting point 145-147 [deg.] C.

  The compound of Example 692 was produced in the same manner as Example 691 using the corresponding starting materials.

Example 692
1- (2,3-Dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine] -1'-yl) -2-[(4-phenylbenzyl) piperazine- 1-yl] ethanone melting point 187-188 ° C.

  4- (2,3-Dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine] -1'-ylacetyl) piperazine-1-carboxylic acid prepared in Example 680 The compounds of Example 693 and Example 694 were produced in the same manner as Example 691 using tert-butyl ester.

Example 693
1- (2,3-Dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine] -1'-ylacetyl) -4- (4-trifluoromethylbenzyl) piperazine Melting point 195-197 ° C (decomposition).

Example 694
1- (2,3-Dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine] -1'-ylacetyl) -4- (4-phenylbenzyl) piperazine melting point 226 -227 [deg.] C (decomposition).

Example 695
4-[(2,3-dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine] -1'-yl) -2-oxoethyl] piperazine-1-carboxylic acid Preparation of (4-Trifluoromethylphenyl) amide 4- [2- (2,3-Dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-) prepared in Example 653 Dissolve piperidine] -1'-yl) -2-oxoethyl] piperazine-1-carboxylic acid tert-butyl ester (300 mg, 0.67 mmol) in 5 ml of methylene chloride, add 10 ml of trifluoroacetic acid and stir for 4 hours at room temperature It stirred. The reaction solution was concentrated under reduced pressure, and 1 ml each of methylene chloride and triethylamine were added. After stirring for 5 minutes at room temperature, the solution was concentrated under reduced pressure, and the residue was dissolved in 10 ml of DMF. Thereto is added a mixture of 4-aminobenzotrifluoride (0.17 ml, 1.33 mmol) and 1,1'-carbonyldiimidazole (220 mg, 1.33 mmol) dissolved in 5 ml of DMF and stirred at room temperature for 3 hours. Stir at room temperature for 2 hours. The reaction mixture was poured into water, extracted with ethyl acetate, and the organic phase was washed with saturated brine. The mixture was dried over magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue is separated and purified by silica gel column chromatography (methylene chloride / methanol = 200/1), crystallized from methylene chloride-isopropyl ether, filtered and dried under reduced pressure to obtain 4-[(2 , 3-Dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine] -1'-yl) -2-oxoethyl] piperazine-1-carboxylic acid (4-trifluoro Methylphenyl) amide (213 mg, 59% yield) was obtained.
Melting point 153.0-155.0 ° C.

Working Example 696
2- {4- [2- (2,3-dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine] -1'-yl) -2-oxoethyl] piperazine Preparation of -1-yl] -N- (4-trifluoromethylphenyl) acetamide The 4- [2- (2,3-dihydro-6-nitro-spiro [imidazo [2,1-b] prepared in Example 653 Trifluoroacetic acid is dissolved in 5 ml of methylene chloride] oxazol-2,4'-piperidine] -1'-yl) -2-oxoethyl] piperazine-1-carboxylic acid tert-butyl ester (300 mg, 0.67 mmol) 10 ml was added and stirred at room temperature for 6 hours. The reaction solution was concentrated under reduced pressure, and 1 ml of methylene chloride and triethylamine were added to the residue. After stirring for 5 minutes at room temperature, the solution was concentrated under reduced pressure. The residue is dissolved in 10 ml DMF, 2-bromo-N- (4-trifluoromethylphenyl) acetamide (207 mg, 0.73 mmol) and triethylamine (0.28 ml, 2.0 mmol) are added and stirred at 100 ° C. for 2 hours did. The reaction mixture was poured into water, extracted with ethyl acetate, and the organic phase was washed with saturated brine. The extract was dried over magnesium sulfate and filtered, and the obtained filtrate was concentrated under reduced pressure. The residue is separated and purified by silica gel column chromatography (methylene chloride / methanol = 100/1), crystallized from methylene chloride-diisopropyl ether, filtered and dried under reduced pressure to obtain 2- {4- [white powder]. 2- (2,3-dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine] -1'-yl) -2-oxoethyl] piperazin-1-yl}- N- [4- (trifluoromethyl) phenyl] acetamide (275 mg, 75% yield) was obtained.
MS 552 (M + 1) ⁺
Melting point 133.0-135.0 ° C.

Example 697
2- [4- (benzoxazol-2-yl) piperazin-1-yl] -1- (2,3-dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4′- Preparation of piperidine] -1′-yl) ethanone The 4- [2- (2,3-dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4′- prepared in Example 653 Dissolve piperidine] -1'-yl) -2-oxoethyl] piperazine-1-carboxylic acid tert-butyl ester (227 mg, 0.50 mmol) in 5 ml of methylene chloride, add 5 ml of trifluoroacetic acid and stir for 4 hours at room temperature It stirred. The reaction solution was concentrated under reduced pressure, and 1 ml of methylene chloride and triethylamine were added to the residue. After stirring for 5 minutes at room temperature, the solution was concentrated under reduced pressure. The residue was dissolved in 5 ml DMF, triethylamine (0.21 ml, 1.52 mmol) and 2-chlorobenzoxazole (86 μl, 0.76 mmol) were added and stirred at 80 ° C. for 2 hours. Water was added to the reaction solution and extracted with methylene chloride. The organic phase was dried over magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue is crystallized from methylene chloride-ethyl acetate, filtered and dried under reduced pressure to give a pale yellow powder of 2- [4- (benzoxazol-2-yl) piperazin-1-yl] -1- (2 3, 3-Dihydro-6-nitro-spiro [imidazo [2,1-b] oxazole-2,4'-piperidine] -1'-yl) ethanone (99 mg, 42%) was obtained.
MS 467 (M ⁺ )
Melting point 260.0-263.0 ° C (decomposition).

  The compounds prepared by the same method as in Example 1-67 above using appropriate starting materials are shown in Tables 26-77 below.

Example 1422
(S) -1- (2-Bromo-4-nitroimidazol-1-yl) -2-methyl-3- {4- [1- (4-trifluoromethoxyphenyl) piperidin-4-yl] piperazine-1- Preparation of yl} propan-2-ol (R) -2-bromo-4-nitro-1- (2-methyl-2-oxiranylmethyl) imidazole (485 mg, 1.75 mmol), 1- [1- A mixture of (4-trifluoromethoxyphenyl) piperidin-4-yl] piperazine (720 mg, 2.19 mmol) and ethanol (10 ml) was stirred at 50 ° C. for 8 hours. The reaction solution is concentrated, and the residue is purified by silica gel column chromatography (methylene chloride / methanol = 20/1) to give yellow amorphous (S) -1- (2-bromo-4-nitroimidazol-1-yl) -2 There were obtained -methyl-3- {4- [1- (4-trifluoromethoxyphenyl) piperidin-4-yl] piperazin-1-yl} propan-2-ol (792 mg, yield 77%).
¹ H-NMR (CDCl ₃ ) δ ppm:
1.13 (3 H, s), 1.50-1. 75 (2 H, m), 1.8 1- 2.00 (2 H, m), 2. 35 (1 H, d, J = 13.9 Hz), 2.40-2.86 (12H, m), 3.57-3. 76 (2H, m), 3.98 (2H, s), 6.89 (2H, d, J = 8.5 Hz), 7.09 (2H, d, J = 8.5 Hz), 8.12 (1 H, s).

  The compounds of Examples 1423 to 1453 shown below were produced in the same manner as in Example 1422.

Example 1423
(S) -4- {4- [3- (2-Chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] piperazin-1-yl} piperidine-1-carboxylic acid tert-butyl ester
¹ H-NMR (CDCl ₃ ) δ ppm:
1.12 (3H, s), 1.29-1.48 (11 H, m), 1.67-1.81 (2 H, m), 2.34 (1 H, d, J = 13.8 Hz), 2.38-2.74 (12H, m), 3.97 (2H, s), 4.02-4.14 (2H, m), 8.05 (1 H, s).

Example 1424
(S) -4- {1- [3- (2-Chloro-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] piperidin-4-yl} piperazine-1-carboxylic acid tert-butyl ester
¹ H-NMR (CDCl ₃ ) δ ppm:
1.11 (3 H, s), 1.38-1.57 (11 H, m), 1.69-1. 86 (2 H, m), 2.24-2.50 (9 H, m), 67-2.79 (1 H, m), 2.86- 3.00 (1 H, m), 3.31-3. 43 (4 H, m), 3.95 (2 H, s), 8.04 ( 1 H, s).

Example 1454
(S) -2-Methyl-6-nitro-2- {4- [1- (4-trifluoromethoxyphenyl) piperidin-4-yl] piperazin-1-ylmethyl} -2,3-dihydroimidazo [2,2, Preparation of 1-b] oxazole (S) -1- (2-bromo-4-nitroimidazol-1-yl) -2-methyl-3- {4- [1- (4-trifluoromethoxyphenyl) piperidine-4 -Yl] piperazin-1-yl} propan-2-ol (790 mg, 1.34 mmol) is dissolved in N, N-dimethylformamide (4 ml) and sodium hydride (69 mg, 1.74) under ice cooling The solution was added with millimoles and stirred at the same temperature for 1 hour. Ethyl acetate (1.3 ml) and water (10 ml) were sequentially added to the reaction solution, and the precipitated crystals were collected by filtration and washed with water. The product is purified by silica gel column chromatography (methylene chloride / methanol = 10/1) and then recrystallized from ethyl acetate / isopropyl ether to give (S) -2-methyl-6-nitro-2- {white powder 4- [1- (4-Trifluoromethoxyphenyl) piperidin-4-yl] piperazin-1-ylmethyl} -2,3-dihydroimidazo [2,1-b] oxazole (270 mg, yield 40%) is obtained The
Melting point: 180-181.5 ° C.

  The compounds of Example 1455 to Example 1465 shown below were produced in the same manner as Example 1454.

Example 1455
(S) -2- {4- [4- (4-chlorophenyl) piperazin-1-yl] piperidin-1-ylmethyl} -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b ] Oxazole yield: 34%
Melting point: 226-228 ° C.

Example 1456
(S) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethoxyphenyl) piperazin-1-yl] piperidin-1-ylmethyl} -2,3-dihydroimidazo [2,2, 1-b] oxazole yield: 23%
Melting point: 193-194 ° C.

Example 1457
(S) -2- {4- [4- (4-chlorobenzyl) piperazin-1-yl] piperidin-1-ylmethyl} -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-] b] Oxazole yield: 25%
Melting point: 148-149 ° C.

Example 1458
(S) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethoxybenzyl) piperazin-1-yl] piperidin-1-ylmethyl} -2,3-dihydroimidazo [2,2, 1-b] oxazole yield: 21%
Melting point: 142-143 ° C.

Example 1459
(S)-(4-Chlorophenyl)-{4- [1- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperidin-4-yl] Piperazin-1-yl} methanone yield: 29%
Melting point: 174-175 ° C.

Example 1460
(S)-{4- [1- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperidin-4-yl] piperazin-1-yl} -(4-Trifluoromethoxyphenyl) methanone yield: 29%
Melting point: 137-138 ° C.

Working Example 1461
(S) -2- {4- [1- (4-chlorobenzyl) piperidin-4-yl] piperazin-1-ylmethyl} -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-] b] Oxazole yield: 24%
Melting point: 168-169 ° C.

Example 1462
(S) -2-Methyl-6-nitro-2- {4- [1- (4-trifluoromethoxybenzyl) piperidin-4-yl] piperazin-1-ylmethyl} -2,3-dihydroimidazo [2,2, 1-b] oxazole yield: 27%
Melting point: 140-141 ° C.

Example 1463
(S)-(4-Chlorophenyl)-{4- [4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] Piperidin-1-yl} methanone yield: 30%
Melting point: 218-220 ° C.

Example 1464
(S)-{4- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] piperidin-1-yl} -(4-Trifluoromethoxyphenyl) methanone yield: 27%
Melting point: 133-134 ° C.

Example 1465
(S) -1 '-(2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) -4- (4-trifluoromethoxyphenoxy)-[1,1 4 '] Bipiperidinyl yield: 41%
Melting point: 131-132 ° C.

Example 1466
(S) -4- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] piperidine-1-carboxylic acid tert Preparation of 4-butyl ester (R) -2-chloro-4-nitro-1- (2-methyl-2-oxiranylmethyl) imidazole (3 g, 13.79 mmol), 4-piperazin-1-yl-piperidine A mixture of -1-carboxylic acid tert-butyl ester (3.9 g, 14.48 mmol) and ethanol (30 ml) was stirred at 50 ° C. for 9 hours. The reaction solution was concentrated, and the residue was purified by silica gel column chromatography (methylene chloride / methanol = 10/1) to obtain a yellow amorphous. This was dissolved in N, N-dimethylformamide (18 ml), sodium hydride (651 mg, 16.28 mmol) was added under ice-cooling, and the mixture was stirred at the same temperature for 1 hour. Ethyl acetate (6 ml) and water (42 ml) were sequentially added to the reaction solution, and the precipitated crystals were collected by filtration and washed with water. This is recrystallized from 2-propanol (20 ml) / water (60 ml) to give (S) -4- [4- (2-methyl-6-nitro-2,3-dihydroimidazo [2] as a slightly yellow powder. 1,1-b] oxazol-2-ylmethyl) piperazin-1-yl] piperidine-1-carboxylic acid tert-butyl ester (4.08 g, 66%).
Melting point: 181-182 ° C.

  The compound of Example 1467 was produced in the same manner as Example 1466.

Working Example 1467
(S) -4- [1- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperidin-4-yl] piperazine-1-carboxylic acid tert -Butyl ester yield: 56%
Melting point: 184-185 ° C.

Example 1468
(S) -4- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] piperidine-1-carboxylic acid 4 Preparation of trifluoromethoxybenzyl ester 4- (trifluoromethoxy) benzyl alcohol (480 mg, 2.50 mmol), 1,1'-carbonylbis-1H-imidazole (405 mg, 2.50 mmol) and N, N- The mixture of dimethylformamide (3 ml) was stirred at room temperature for 14 hours.

  On the other hand, (S) -4- [4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] piperidine-1-carboxylic acid Acid tert-butyl ester (750 mg, 1.66 mmol) was dissolved in methylene chloride (5 ml), trifluoroacetic acid (5 ml) was added and stirred at room temperature for 14 hours. The reaction mixture was concentrated, methanol (5 ml) and triethylamine (5 ml) were added to the residue, and the mixture was stirred at room temperature for 10 minutes and concentrated. The residue was dissolved in N, N-dimethylformamide (5 ml), added to the previous N, N-dimethylformamide solution, and stirred at 50 ° C. for 3 hours.

The reaction was brought to room temperature, poured into water (40 ml) and extracted twice with ethyl acetate (30 ml). The organic phases were combined, washed twice with water (40 ml), then with saturated brine (30 ml) and dried over sodium sulfate. After filtering the organic phase, the filtrate is concentrated, and the residue is purified by silica gel column chromatography (methylene chloride / methanol = 10/1) and then recrystallized from ethyl acetate / isopropyl ether to obtain (S) of light tea powder. 4- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazin-1-yl] piperidine-1-carboxylic acid 4-trifluoro The methoxy benzyl ester (545 mg, 58%) was obtained.
Melting point: 105-106 ° C.

  The compound of Example 1469 was produced in the same manner as Example 1468.

Example 1469
(S) -4- [1- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperidin-4-yl] piperazine-1-carboxylic acid 4 -Trifluoro methoxy benzyl ester yield: 64%
Melting point: 110-111 ° C.

Example 1470
(S) -2-Methyl-6-nitro-2- [4- {1- [3- (4-trifluoromethoxyphenyl) -2-propenyl] piperidin-4-yl} piperazin-1-ylmethyl] -2 Of (S) -4- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole-2-), Preparation of 3, 3-dihydroimidazo [2, 1-b] oxazole Ylmethyl) piperazin-1-yl] piperidine-1-carboxylic acid tert-butyl ester (750 mg, 1.66 mmol) is dissolved in methylene chloride (5 ml), trifluoroacetic acid (5 ml) is added and 1 Stir for .5 hours. The reaction mixture was concentrated, methylene chloride (5 ml) and triethylamine (5 ml) were added to the residue, and the mixture was stirred at room temperature for 10 minutes and concentrated. The residue is dissolved in 1,2-dichloroethane (20 ml) and 3- (4-trifluoromethoxyphenyl) propenal (396 mg, 1.83 mmol) and sodium triacetoxyborohydride (564 mg, 2.66 mmol) are added The mixture was stirred at room temperature for 3.5 hours. The reaction mixture was washed successively with saturated aqueous sodium bicarbonate solution (15 ml), water (20 ml) and saturated brine (20 ml), and dried over sodium sulfate. The reaction solution is filtered, the filtrate is concentrated, and the residue is purified by silica gel column chromatography (methylene chloride / methanol = 10/1) and then recrystallized from methanol / water to obtain (S)-a slightly yellow powder. 2-Methyl-6-nitro-2- [4- {1- [3- (4-trifluoromethoxyphenyl) -2-propenyl] piperidin-4-yl} piperazin-1-ylmethyl] -2,3-dihydro The imidazo [2,1-b] oxazole (446 mg, 49%) was obtained.
Melting point: 157-158 ° C.

  In the same manner as in Example 1470, the compounds of Example 1471 to Example 1497 shown below were produced.

Example 1471
(S) -2-Methyl-6-nitro-2- [4- {4- [3- (4-trifluoromethoxyphenyl) -2-propenyl] piperazin-1-yl} piperidin-1-ylmethyl] -2 3, 3-dihydroimidazo [2,1-b] oxazole melting point: 174-175 ° C.

Example 1472
(S) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethoxyphenoxy) phenyl] piperazin-1-ylmethyl} -2,3-dihydroimidazo [2,1-b] Oxazole 4-toluenesulfonate melting point: 146.1-148.6 ° C.

Working Example 1473
(S) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethoxyphenoxy) phenyl] piperazin-1-ylmethyl} -2,3-dihydroimidazo [2,1-b] Oxazole • hydrochloride melting point: 133-137 ° C.

  In the same manner as in Example 649, the following compounds were produced.

  In the same manner as in Example 652, the following compounds were produced.

  In the same manner as in Example 128, the compounds of Example 1510 to Example 1888 shown below were produced.

Example 1510
(R) -2-Methyl-6-nitro-2- {4- [1- (4-trifluoromethoxybenzyl) piperidin-4-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b ] Oxazole melting point: 186-188 ° C.

Example 1511
(R) -6-Nitro-2- {4- [4- (4-trifluoromethoxyphenoxy) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole melting point: 157-160 ° C.

Example 1512
(R) -2-Methyl-6-nitro-2- {4- [3- (4-trifluoromethoxyphenoxy) -8-azabicyclo [3.2.1] octan-8-yl] phenoxymethyl} -2 3, 3-dihydroimidazo [2, 1-b] oxazole 4-toluenesulfonate melting point: 207.2-208.0 ° C (decomposition).

Example 1513
2-Methyl-6-nitro-2- [4- (4-trifluoromethoxyphenoxy) benzyloxymethyl] -2,3-dihydroimidazo [2,1-b] oxazole melting point: 107.9-109. 3 ° C.

Example 1514
6-Nitro-2- {4- [4- (4-trifluoromethoxyphenoxy) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole melting point: 173. 2-177.3 ° C.

Example 1515
2-Methyl-6-nitro-2- {4- [4- (4-chlorophenoxy) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole melting point: 151.0-152.3 ° C.

Example 1516
(S) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethoxyphenoxy) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b Mp: 199.0-200.5 ° C.

Example 1889
(R) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethoxyphenoxy) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b Preparation of Oxazole] 4- [4- (4-Trifluoromethoxyphenoxy) piperidin-1-yl] phenol (693 mg, 1.96 mmol) was dissolved in N, N'-dimethylformamide (3 ml) and cooled with ice. Sodium hydride (86 mg, 2.16 mmol) was added and stirred at 70-75.degree. C. for 20 minutes. This mixture is ice-cooled and (R) -2-bromo-4-nitro-1- (2-methyl-2-oxiranylmethyl) imidazole (720 mg, 2.75 mmol) in N, N'-dimethylformamide The solution dissolved in (3 ml) was added and stirred at 70-75 ° C. for 20 minutes. The reaction solution was cooled to room temperature, ice water (25 ml) was added, and the mixture was extracted three times with methylene chloride (50 ml). The organic phases were combined, washed three times with water and then dried over magnesium sulfate. After filtering the organic phase under reduced pressure, the filtrate is concentrated, and the residue is purified by silica gel column chromatography (methylene chloride / ethyl acetate = 3/1) and recrystallized from ethyl acetate / isopropyl ether to give a pale yellow powder ( R) -2-methyl-6-nitro-2- {4- [4- (4-trifluoromethoxyphenoxy) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] Oxazole (343 mg, 33%) was obtained.

Example 1890
(1) (S) -4- [3- (2-bromo-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] piperazine-1-carboxylic acid 3- (4-trifluoromethyl) Preparation of phenyl) -2-propenyl ester (R) -2-bromo-4-nitro-1- (2-methyl-2-oxiranylmethyl) imidazole (2.04 g, 7.78 mmol), piperazine-1 A mixture of 3- (4-trifluoromethylphenyl) -2-propenyl ester (2.69 g, 8.56 mmol) and N, N'-dimethylformamide (10 ml) was stirred at 50 ° C. for 20 hours . The reaction solution was cooled to room temperature, water (45 ml) was added, and the mixture was extracted twice with ethyl acetate (15 ml). The organic phases are combined, washed three times with water and dried over sodium sulfate. The organic phase is filtered under reduced pressure, the filtrate is concentrated, and the residue is purified by silica gel column chromatography (n-hexane / ethyl acetate = 1/2) to give (S) -4- [3- (yellow oil). (2-Bromo-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] piperazine-1-carboxylic acid 3- (4-trifluoromethylphenyl) -2-propenyl ester (3.77 g, 84%).
¹ H-NMR (CDCl ₃ ) δ ppm:
1.16 (3 H, s), 2.36 (1 H, d, J = 14.0 Hz), 2.43-2.76 (5 H, m), 3.21 (1 H, s), 3.41- 3.57 (4H, m), 4.01 (2H, s), 4.78 (2H, dd, J = 1.0 Hz, 6.1 Hz), 6.29-6.43 (1 H, m), 6.66 (1 H, d, J = 16.0 Hz), 7.48 (2 H, d, J = 8.3 Hz), 7.58 (2 H, d, J = 8.3 Hz), 8.10 (1 H , S).

(2) (S) -4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid 3- (4-trifluoro) Preparation of methylphenyl) -2-propenyl ester (S) -4- [3- (2-bromo-4-nitroimidazol-1-yl) -2-hydroxy-2-methylpropyl] piperazine-1-carboxylic acid 3 A solution of-(4-trifluoromethylphenyl) -2-propenyl ester (3.5 g, 6.07 mmol) in N, N'-dimethylformamide (10.5 ml) was dissolved in sodium hydride (ice cold) Add 316 mg (7.89 mmol) and stir at the same temperature for 1.5 hours. Ethyl acetate (3.5 ml) and water (24.5 ml) were added to the reaction solution, and the mixture was stirred for 30 minutes. The precipitated crystals were collected by filtration and washed with water. The product is purified by silica gel column chromatography (ethyl acetate) and then recrystallized from 2-propanol / water to give (S) -4- (2-methyl-6-nitro-2, 3-Dihydroimidazo [2,1-b] oxazol-2-ylmethyl) piperazine-1-carboxylic acid 3- (4-trifluoromethylphenyl) -2-propenyl ester (2.07 g, 69%) was obtained.

Reference Example 448
Preparation of 1- [4- (tetrahydropyran-2-yloxy) phenyl] -4- [N- (4-chlorophenyl) -N-methylamino] piperidine 4- [N- (4-chlorophenyl) -N-methylamino Piperidine (2.52 g, 11.22 mmol), 2- (4-bromophenoxy) tetrahydropyran (2.89 g, 11.22 mmol), palladium acetate (50 mg, 0.22 mmol), (S)-( −)-2,2-bis (diphenylphosphino) -1,1′-binaphthyl (BINAP) (212 mg, 0.34 mmol) and sodium tert-butoxy (1.51 g, 15.71 mmol) under a nitrogen atmosphere The mixture was heated to reflux for 3 hours in toluene (30 ml). Ethyl acetate and water were added to the reaction solution, the mixture was stirred and the precipitate was removed by celite filtration, and the filtrate was extracted with ethyl acetate. The organic phase was washed with brine, dried over magnesium sulfate and filtered. The obtained filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (n-hexane / ethyl acetate = 20/1) to obtain 1- [4- (tetrahydropyran-2-yloxy) phenyl] as a pale yellow powder. There was obtained -4- [N- (4-chlorophenyl) -N-methylamino] piperidine (1.33 g, yield 30%).
¹ H-NMR (CDCl ₃ ) δ ppm:
1.50-2.04 (10H, m), 2.68-2.80 (2H, m), 2.78 (3H, s), 3.50-3. 70 (4H, m), 85-4.03 (1 H, m), 5.31 (1 H, t, J = 5.7 Hz), 6.72 (2 H, d, J = 9.1 Hz), 6. 90 (2 H, d, J = 9.2 Hz), 6.98 (2H, d, J = 9.2 Hz), 7.17 (2H, d, J = 9.1 Hz).

Reference Example 449
Preparation of 4- {4- [N- (4-chlorophenyl) -N-methylamino] piperidin-1-yl} phenol 1- [4- (tetrahydropyran-2-yloxy) phenyl] -4- [N- ( 4-Chlorophenyl) -N-methylamino] piperidine (1.33 g, 3.32 mmol) is suspended in ethanol (80 ml), pyridinium p-toluenesulfonate (0.25 g, 1 mmol) is added, 70 Stir at 8 ° C for 8 hours. Ethanol was distilled off under reduced pressure, and methylene chloride and saturated aqueous sodium hydrogen carbonate solution were added to the residue and stirred. This was extracted with methylene chloride, dried over magnesium sulfate and filtered. The obtained filtrate is concentrated under reduced pressure, methylene chloride and n-hexane are added to the residue, and the resulting precipitate is collected by filtration to give a pale pink powder of 4- {4- [N- (4-chlorophenyl)- N-Methylamino] piperidin-1-yl} phenol (922.5 mg, 88% yield) was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.79-2.04 (4H, m), 2.67-2.79 (2H, m), 2.79 (3H, s), 3.56-3.68 (2H, m), 4. 48 (1 H, s), 6.69-6.80 (4 H, m), 6.85-6. 92 (2 H, m), 7.14-7.21 (2 H, m).

  The following compounds were produced in the same manner as in Reference Example 448 and Reference Example 449. In the following table, Ph means phenyl or phenylene.

Reference Example 450
(4-Chlorophenyl)-(4-hydroxyphenyl) methanone O-methyl oxime Ms: 261 (M ⁺ ).

Reference Example 451
(4-hydroxyphenyl)-(4-trifluoromethylphenyl) methanone O-methyl oxime Ms: 295 (M ⁺ ).

Example 1891
(R) -2-Methyl-6-nitro-2- {2- [4- (4-trifluoromethoxybenzyl) -piperazin-1-yl] benzothiazol-6-yloxymethyl} -2,3-dihydro Preparation of imidazo [2,1-b] oxazole (R) -2-Chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitro-1H-imidazole (51 mg, 0.23 mmol And 6-hydroxy-2- [4- (4-trifluoromethoxybenzyl) -piperazin-1-yl] -benzothiazole (80 mg, 0.20 mmol) in DMF (5 ml), sodium hydride (10 mg, 0.25 mmol) was added and stirred at 60 ° C. for 1.5 hours. After allowing to cool to room temperature, water is added to the reaction mixture, and the mixture is extracted with ethyl acetate. The combined organic layer is washed with water and brine, and dried over sodium sulfate. After filtration, the filtrate is concentrated under reduced pressure. The residue is purified by silica gel column chromatography (n-hexane: ethyl acetate = 1: 3 → ethyl acetate), recrystallized from ethanol, and (R) -2-methyl-6-nitro-2- {colorless powder crystal 2- [4- (4-trifluoromethoxybenzyl) -piperazin-1-yl] benzothiazole-6-yloxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole (40 mg, The rate is 33%).
Melting point: 205.6-207.4 ° C.

Example 1892
(R) -2-Methyl-6-nitro-2- {2- [4- (4-trifluoromethoxyphenoxy) piperidin-1-yl} pyridin-5-oxy] methyl-2,3-dihydro-imidazo [ Preparation of 2,1-b] oxazole 0.67 g (1.9 mmol) and (R) of 5-hydroxy-2- {4- [4- (trifluoromethoxy) phenoxy] piperidin-1-yl} pyridine 0.51 g (2.4 mmol) of 2-chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitro-1H-imidazole was dissolved in 6.7 ml of DMF. 91 mg (2.3 millimoles) of sodium hydride was added to this, and it heat-stirred at 50-55 degreeC for 1 hour. The reaction mixture was poured into water and extracted with methylene chloride. The organic layer was washed with brine, dried over magnesium sulfate and filtered with suction. The resulting filtrate was concentrated under reduced pressure. The residue is separated and purified by silica gel column chromatography (methylene chloride / ethyl acetate = 10/0, 9/1, 8/2) and further crystallized by methylene chloride / diisopropyl ether / ethyl acetate to give pale yellow powder (R ) -2-Methyl-6-nitro-2- {2- [4- (4-trifluoromethoxyphenoxy) piperidin-1-yl] pyridin-5-oxy] methyl-2,3-dihydro-imidazo [2,2, 0.30 g (29%) of 1-b] oxazol was obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.77 (3H, s), 1.80-1.94 (2H, m), 1.94-2.17 (2H, m), 3.21-3. 44 (2H, m), 3. 67-3.89 (2H, m), 3.96-4. 11 (2H, m), 4.19 (1H, d, J = 10.4 Hz), 4.36-4.59 (2H, m) ), 6.65 (1 H, d, J = 9.2 Hz), 6.83-6.97 (2 H, m), 7.02-7.20 (3 H, m), 7.56 (1 H, s) ), 7.87 (1 H, d, J = 3.0 Hz).

  The following compounds were prepared as in Example 1892 above. In the following table, Ph means phenyl or phenylene.

Example 1893
(R) -2- (4- {4- [N- (4-chlorophenyl) -N-methylamino] piperidin-1-yl} phenoxymethyl) -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole melting point: 173.7-175.1 ° C.

Example 1894
(R) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethoxybenzyl) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b ] Oxazole
¹ H-NMR (CDCl ₃ ) δ ppm:
1.23-1.52 (2H, m), 1.52-1.66 (3H, m), 1.66-1.89 (3H, m), 2.43-2.70 (4H, m) ), 3.50 (2 H, d, J = 12.1 Hz), 3.91-4.09 (2 H, m), 4.16 (1 H, d, J = 10.1 Hz), 4.48 (1 H) , D, J = 10.2 Hz), 6.66-6.81 (2H, m), 6.81-6.95 (2H, m), 7.05-7.23 (4H, m), 7 .54 (1 H, s)
Melting point: 210.9-212.4 ° C
[Α] _D = -9.0 ° (concentration: 1.0, CHCl _3).

Example 1895
(R) -2- {4- [4- (3,4-dichlorobenzyl) piperidin-1-yl] phenoxymethyl} -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b ] Oxazole
¹ H-NMR (CDCl ₃ ) δ ppm:
1.24-1.52 (2H, m), 1.52-1.64 (4H, m), 1.64-1.73 (1H, m), 1.73-1.87 (4H, m) ), 2.38-2.68 (4H, m), 3.49 (2H, d, J = 12.1 Hz), 3.91-4.09 (2H, m), 4.16 (1H, d) , J = 10.2 Hz), 4.49 (1 H, d, J = 10.2 Hz), 6.67-6.81 (2 H, m), 6.8 1-6. 92 (2 H, m), 6 .94-7.07 (1 H, m), 7. 25 (1 H, s), 7. 35 (1 H, d, J = 8.2 Hz), 7.55 (1 H, s)
Melting point: 180.0-181.2 ° C
[Α] _D = -8.5 ° (concentration: 1.0, CHCl _3).

Example 1896
(R) -6-Nitro-2- {4- [4- (4-trifluoromethoxybenzyloxymethyl) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole Melting point: 140.4-141.7 ° C.

Example 1897
(R) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethylbenzyloxymethyl) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1 -B] Oxazole melting point: 172.3-172.9 <0> C.

Example 1898
(R) -2-Methyl-6-nitro-2- (4- {4- [3- (4-trifluoromethylphenyl) -2-propenyl] piperazin-1-yl} phenoxymethyl) -2,3- Dihydroimidazo [2,1-b] oxazole melting point: 199.7-202 ° C.

Example 1899
(R) -2-Methyl-6-nitro-2- (4- {4- [2- (4-trifluoromethoxyphenoxy) ethyl] piperazin-1-yl} phenoxymethyl) -2,3-dihydroimidazo [ 2,1-b] oxazole melting point: 194.8-195.6 ° C.

Example 1900
(R) -2- (4- {4- [N- (4-chlorophenyl) -N-ethylamino] piperidin-1-yl} phenoxymethyl) -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole melting point: 121.4-125 ° C.

Working Example 1901
(R) -2- (4- {4- [N-ethyl-N- (4-trifluoromethoxyphenyl) amino] piperidin-1-yl} phenoxymethyl) -2-methyl-6-nitro-2,3 Dihydroimidazo [2,1-b] oxazole melting point: 122.5-122.8 ° C.

Working Example 1902
(R) -2- (4- {4- [N-ethyl-N- (4-trifluoromethylphenyl) amino] piperidin-1-yl} phenoxymethyl) -2-methyl-6-nitro-2,3 Dihydroimidazo [2,1-b] oxazole melting point: 105-108.5 ° C.

Working Example 1903
(R) -2- {4- [4- (5-chlorobenzofuran-2-ylmethyl) piperazin-1-yl] phenoxymethyl} -2-methyl-6-nitro-2,3-dihydroimidazo [2,1 -B] oxazole melting point: 210.6-211.6 ° C.

Working Example 1904
(R) -2-Methyl-6-nitro-2- {2- [4- (4-trifluoromethoxybenzyl) piperazin-1-yl] benzothiazol-6-yloxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole melting point: 203.9-205.2 ° C.

Example 1905
2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethoxybenzyl) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole melting point: 180.9-182.7 ° C.

Working Example 1906
2- {4- [4- (3,4-dichlorobenzyl) piperidin-1-yl] phenoxymethyl} -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole Melting point: 191.4-192.1 ° C.

Example 1907
2- (4- {4- [N- (4-chlorophenyl) -N-methylamino] piperidin-1-yl} phenoxymethyl) -2-methyl-6-nitro-2,3-dihydroimidazo [2,1 -B] Oxazole melting point: 137.6-141.5 ° C.

Working Example 1908
(R) -2- (4- {4- [N- (4-chlorophenyl) -N-methylamino] piperidin-1-yl} phenoxymethyl) -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole 4-toluenesulfonate melting point: 212.6-214.1 ° C.

Example 1909
(R) -2- (4- {4- [N- (4-chlorophenyl) -N-methylamino] piperidin-1-yl} phenoxymethyl) -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole methanesulfonate melting point: 171.2-172.8 ° C.

Example 1910
(R) -2- (4- {4- [N- (4-chlorophenyl) -N-methylamino] piperidin-1-yl} phenoxymethyl) -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole hydrochloride melting point: 170.0-173.7 ° C.

Example 1911
2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethoxybenzyloxymethyl) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] Oxazole melting point: 153.1-153.7 ° C.

Example 1912
(R)-(4-Chlorophenyl) carbamic acid 1- [4- (2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) phenyl] piperidine-4- Methyl ester melting point: 211.6-212.3 ° C (decomposition).

Example 1913
2-Methyl-6-nitro-2- {4- [4- (4-triflomethylbenzyloxymethyl) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] Oxazole melting point: 138.7-139.5 ° C.

Example 2988
(R) -2-Methyl-2- {4- [N-methyl-N- (1-methylpiperidin-4-yl) amino] phenoxymethyl} -6-nitro-2,3-dihydroimidazo [2,1 -B] oxazole Example 2989
(R) -4- {1- [4- (2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) phenyl] -3- (4-trifluoro Methoxyphenyl) ureido} piperidine-1-carboxylic acid (4-trifluoromethoxyphenyl) amide Example 2990
6-Nitro-2- {4- [4- (4-trifluoromethoxybenzyloxymethyl) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole melting point: 140. 2-141.7 ° C.

Example 2991
(R) -2-Methyl-6-nitro-2- {4- [4- (tetrahydropyran-2-yloxymethyl) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1 -B] Oxazole melting point: 217.6-218.6 ° C.

Example 2992
(R) -2-Methyl-6-nitro-2- {4- [4- (hydroxymethyl) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole melting point: 213.3-215.3 ° C.

Example 2993
2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethoxyphenoxy) piperidin-1-yl] benzyl} -2,3-dihydroimidazo [2,1-b] oxazole melting point: 184 9-186.8 ° C.

Example 2994
(R) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethoxyphenyl) carbamoyloxymethylpiperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,2, 1-b] Oxazole melting point: 211.6-212.0 ° C. (decomposition).

Example 2995
(R) -2- {4- [4- (biphenyl-4-yloxymethyl) piperidin-1-yl] phenoxymethyl} -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-] b] Oxazole melting point: 245 ° C. (decomposition).

Example 2996
(R) -2- {1-benzyl-2- [4- (4-trifluoromethoxybenzyl) piperazin-1-yl] -1H-benzimidazole-5-yloxymethyl} -2-methyl-6-nitro- 2,3-dihydroimidazo [2,1-b] oxazole melting point: 101.3-104.0 ° C.

Example 2997
(R) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethoxybenzyl) piperidin-1-ylmethyl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b ] Oxazole melting point: 172.5-174.1 ° C.

Example 2998
2- {4- [4- (N-methyl-tert-butoxycarbonylamino) piperidin-1-ylmethyl] phenoxymethyl}
2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole melting point: 138.5-141.9 ° C.

Example 2999
(R) -2- [4 '-(4-tert-butoxycarbonyl-1,4-diazepan-1-yl) biphenyl-4-yloxymethyl] -2-methyl-6-nitro-2,3-dihydro Imidazo [2,1-b] oxazole melting point: 213.8-215.7 ° C.

Example 3000
(R) -2- [4 '-(4-tert-butoxycarbonyl-1,4-diazepan-1-yl) biphenyl-4-yloxymethyl] -6-nitro-2,3-dihydroimidazo [2,2, 1-b] oxazole melting point: 235.5-237.5 ° C.

Embodiment 3001
(S) -2-Methyl-2- (N-methyl-N- {4- [N-methyl-N- (4-trifluoromethylcinnamyl) amino] benzyl} aminomethyl) -6-nitro-2, 3-Dihydroimidazo [2,1-b] oxazole melting point: 153.5-154.5 ° C.

Embodiment 3002
(R) -2-Methyl-6-nitro-2- (4- {2-oxo-2- [4- (4-trifluoromethoxyphenoxy) piperidin-1-yl] ethylaminocarbonyl} phenoxymethyl) -2 , 3-Dihydroimidazo [2,1-b] oxazole melting point: 186.9-189.5 ° C.

Embodiment 3003
2-Methyl-6-nitro-2- {2- [4- (4-trifluoromethoxybenzyl) piperazin-1-yl] benzothiazol-6-yloxymethyl} -2,3-dihydroimidazo [2,1 -B] Oxazole melting point: 172.6-174.6C.

Embodiment 3004
2- {4- [4- (4-chlorophenoxymethyl) piperidin-1-yl] phenoxymethyl} -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole melting point: 190 .0-190.4 ° C.

Embodiment 3005
2- {4- [4- (4-chlorophenoxymethyl) piperidin-1-yl] phenoxymethyl} -6-nitro-2,3-dihydroimidazo [2,1-b] oxazole melting point: 191.2-192 .5 ° C.

Embodiment 3006
6-nitro-2- {4- [4- (4-trifluoromethoxybenzyl) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole melting point: 132.7- 135.0 ° C.

Embodiment 3007
2-Methyl-6-nitro-2- (4- (4- (4- (4-trifluoromethoxycinnamyl) piperazin-1-yl) phenoxymethyl) -2,3-dihydroimidazo [2,1-b] oxazole melting point 181.1-182.2 ° C.

Example 3353
(R) -2- {4- [4- (4-chlorophenyl) oxazol-2-yl] phenoxymethyl} -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole Preparation (R) 2-Chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitro-1H-imidazole 1.73 g (7.9 mmol), 4- [4- (4-chlorophenyl) 1.80 g (6.6 millimoles) of oxazol-2-yl] phenol and 0.42 g (2.0 millimoles) of potassium phosphate were suspended in 15 ml of ethanol and heated under reflux for 3 hours under argon and stirred. The reaction mixture was concentrated, dichloromethane was added to the residue, and insolubles were filtered off. The filtrate is concentrated and the residue is dissolved in 20 ml DMF. Under ice cooling, 0.29 g (7.3 mmol) of 60% sodium hydride was added and the mixture was stirred for 6 hours. The solvent was distilled off under reduced pressure, and 100 ml of acetone and 10 ml of silica gel were added to the residue and concentrated. The residue was purified by silica gel column chromatography (dichloromethane: methanol = 50: 1 to 30: 1) and crystallized from a dichloromethane-ethanol mixed solvent. Recrystallization from an acetone-water mixed solvent gives a pale brown powder of (R) -2- {4- [4- (4-chlorophenyl) oxazol-2-yl] phenoxymethyl} -2-methyl-6-nitro- 1.15 g (yield 38%) of 2,3-dihydroimidazo [2,1-b] oxazole was obtained.
Melting point: 248.8-251.5 ° C.

Example 3354
6-((R) -2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) -2- [4- (4-trifluoromethoxybenzyl) piperidine- Preparation of 1-yl] quinoline (R) -2-Chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitro-1H-imidazole 0.65 g and 6-hydroxy-2- [4-] 1.00 g of (4-trifluoromethoxybenzyl) piperidin-1-yl] quinoline and 0.16 g of potassium phosphate were suspended in 10 ml of ethanol, and heated under reflux under argon atmosphere for 4 hours and stirred. The reaction mixture was concentrated, and the residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 1: 3 → ethyl acetate) and concentrated. The obtained residue was dissolved in DMF (10 ml), 99 mg of sodium hydride was added, and the mixture was stirred at room temperature for 1 hour. Water was added to the reaction solution, and extracted with ethyl acetate. The combined organic layer was washed with water and saturated brine and then dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (n-hexane: ethyl acetate = 1: 1 → 1: 3) and recrystallized from ethanol to give 6-((R) -2-methyl-6 of pale yellow powdery crystals. -Nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) -2- [4- (4-trifluoromethoxybenzyl) piperidin-1-yl] quinoline 0.57 g (36%) I got
Melting point: 184.9-185.9 ° C.

Example 3355
6-((R) -2-Methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazol-2-ylmethoxy) -2- [4- (4-trifluoromethoxybenzylidene) piperidine- Preparation of 1-yl] quinoline (R) -2-Chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitro-1H-imidazole 0.66 g and 6-hydroxy-2- [4- 0.94 g of (4-trifluoromethoxybenzylidene) -piperidin-1-yl] quinoline and 0.15 g of potassium phosphate were suspended in 10 ml of ethanol and stirred under heating at reflux for 6 hours under an argon atmosphere. The reaction mixture was concentrated, and the residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 1: 3 → ethyl acetate) and concentrated. The obtained residue was dissolved in DMF (10 ml), 99 mg of sodium hydride was added, and the mixture was stirred at room temperature for 3 hours. Ethyl acetate was added to the reaction solution and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (dichloromethane: methanol = 50: 1) and recrystallized from ethanol to give 6-((R) -2-methyl-6-nitro-2,3-dihydro of yellow powdery crystals. 1.37 g (51%) of imidazo [2,1-b] oxazol-2-ylmethoxy) -2- [4- (4-trifluoromethoxybenzylidene) piperidin-1-yl] quinoline were obtained.
Melting point: 193.9-195.9 ° C.

Example 3356
(R) -2-Methyl-6-nitro-2- {6- [4- (4-trifluoromethoxyphenoxy) piperidin-1-yl] naphthalen-2-yloxymethyl} -2,3-dihydroimidazo [ Preparation of 2,1-b] oxazole (R) -2-Chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitro-1H-imidazole 2.12 g and 6- [4- (4) 3.02 g of -Trifluoromethoxyphenoxy) piperidin-1-yl] naphthalen-2-ol and 0.48 g of potassium phosphate were suspended in 30 ml of ethanol and stirred under heating under reflux for 6 hours under nitrogen atmosphere. Water was added to the reaction solution and extracted with dichloromethane. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 1: 3 → ethyl acetate) and concentrated to give 2.73 g of yellow powder. This was dissolved in DMF (27 ml), 0.21 g of sodium hydride was added, and the mixture was stirred at room temperature for 2.5 hours. Saturated brine was added to the reaction solution, and extracted with dichloromethane. The combined organic layer was washed with water and saturated brine and then dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane: ethyl acetate = 4: 1). Recrystallization from a dichloromethane-ethyl acetate-diisopropyl ether mixed solvent and light yellow powdery crystals of (R) -2-methyl-6-nitro-2- {6- [4- (4-trifluoromethoxyphenoxy) piperidine-1 1.05 g (24% yield) of [-yl] naphthalen-2-yloxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole were obtained.
Melting point: 204.8-207.9 ° C.

Example 3357
(R) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethoxybenzyloxy) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-] b) Preparation of oxazole 0.305 g of 4- [4- (4-trifluoromethoxybenzyloxy) piperidin-1-yl] phenol is dissolved in DMF (5 ml), 10 mg of sodium hydride is added, and the temperature is 70-80 ° C. The mixture was stirred for 20 minutes. Under ice-cooling, 0.252 g of (R) -2-chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitro-1H-imidazole was added, and the mixture was stirred at 70 to 80 ° C. for 20 minutes. After cooling to room temperature, water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The combined organic layer was washed with water and saturated brine and then dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 1: 3 → ethyl acetate). Recrystallization from a dichloromethane-ethyl acetate mixed solvent, and (R) -2-methyl-6-nitro-2- {4- [4- (4-trifluoromethoxybenzyloxy) piperidin-1-yl] as colorless powder crystals. 88 mg (26.7%) of phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole were obtained.
Melting point: 214.3-217.7 ° C.

Example 3358
(R) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethylbenzyloxy) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1- b) Preparation of oxazole 0.217 g of 4- [4- (4-trifluoromethylbenzyloxy) piperidin-1-yl] phenol is dissolved in DMF (5 ml), 27 mg of sodium hydride is added, and the temperature is 70-80 ° C. The mixture was stirred for 20 minutes. Under ice cooling, 0.188 g of (R) -2-chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitro-1H-imidazole was added, and the mixture was stirred at 70-80 ° C. for 20 minutes. After cooling to room temperature, water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The combined organic layer was washed with water and saturated brine and then dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 1: 3 → ethyl acetate). Recrystallization from a dichloromethane-ethyl acetate mixed solvent and light yellow powder of (R) -2-methyl-6-nitro-2- {4- [4- (4-trifluoromethylbenzyloxy) piperidin-1-yl] 88 mg (26.7%) of phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole were obtained.
Melting point: 217.4-219.7 ° C.

Example 3359
(R) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethoxybenzyl) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b Preparation of Oxazole] Dissolve 8.41 g of 4- [4- (4-trifluoromethoxybenzyl) piperidin-1-yl] phenol in DMF (84 ml), add 1.05 g of sodium hydride, and adjust to 70-80 ° C. The mixture was stirred for 20 minutes. Under ice cooling, 7.29 g of (R) -2-chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitro-1H-imidazole was added, and the mixture was stirred at 70-80 ° C. for 20 minutes. After cooling to room temperature, water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The combined organic layer was washed with water and saturated brine and then dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane: ethyl acetate = 9: 1). Recrystallization from a dichloromethane-ethyl acetate mixed solvent and light yellow powder of (R) -2-methyl-6-nitro-2- {4- [4- (4-trifluoromethoxybenzyl) piperidin-1-yl] phenoxy 4.65 g (36.5%) of methyl} -2,3-dihydroimidazo [2,1-b] oxazole were obtained.
¹ H-NMR (CDCl ₃ ) δ ppm:
1.23-1.52 (2H, m), 1.52-1.66 (3H, m), 1.66-1.89 (3H, m), 2.43-2.70 (4H, m) ), 3.50 (2 H, d, J = 12.1 Hz), 3.91-4.09 (2 H, m), 4.16 (1 H, d, J = 10.1 Hz), 4.48 (1 H) , D, J = 10.2 Hz), 6.66-6.81 (2H, m), 6.81-6.95 (2H, m), 7.05-7.23 (4H, m), 7 .54 (1 H, s)
Melting point: 210.9-212.4 ° C
^{[Α] D = -9.0 ° (} c = 1.0, CHCl 3).

Example 3360
(R) -2- {4- [4- (4-chlorobenzyl) piperidin-1-yl] phenoxymethyl} -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole Into DMF (5 ml) was dissolved 1.036 g of 4- [4- (4-chlorobenzyl) piperidin-1-yl] phenol, 151 mg of sodium hydride was added, and the mixture was stirred at 70-80 ° C. for 20 minutes. Under ice-cooling, 1.04 g of (R) -2-chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitro-1H-imidazole was added, and the mixture was stirred at 70 to 80 ° C. for 20 minutes. After cooling to room temperature, water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The combined organic layer was washed with water and saturated brine and then dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 1: 3 → ethyl acetate). Recrystallization from a dichloromethane-ethyl acetate mixed solvent gave pale yellow powdery crystals of (R) -2- {4- [4- (4-chlorobenzyl) piperidin-1-yl] phenoxymethyl} -2-methyl-6- 0.286 g (17.3%) of nitro-2,3-dihydroimidazo [2,1-b] oxazole were obtained.
Melting point: 207.1-211.2 ° C.

Example 3361
(R) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethoxycinnyloxy) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1 -B] Preparation of oxazole Dissolve 2.21 g of 4- [4- (4-trifluoromethoxycinnyloxy) piperidin-1-yl] phenol in DMF (22 ml) and add 0.247 g of sodium hydride, It stirred at 70-80 degreeC for 20 minutes. While cooling with ice, 1.71 g of (R) -2-chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitro-1H-imidazole was added, and the mixture was stirred at 70-80 ° C. for 20 minutes. After cooling to room temperature, water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The combined organic layer was washed with water and saturated brine and then dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane: ethyl acetate = 9: 1). Recrystallization from a dichloromethane-ethyl acetate mixed solvent and light yellow powdery crystals of (R) -2-methyl-6-nitro-2- {4- [4- (4-trifluoromethoxycinnyloxy) piperidine-1-] 0.70 g (21.7%) of yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole was obtained.
Melting point: 213.7-217.4 ° C.

Example 3362
(R) -6-Nitro-2- {4- [4- (4-trifluoromethoxybenzyloxy) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole Preparation 4.60 g of 4- [4- (4-trifluoromethoxybenzyloxy) piperidin-1-yl] phenol are dissolved in DMF (46 ml), 0.55 g of sodium hydride is added and 20 at 70-80 ° C. Stirred for a minute. Under ice cooling, 3.57 g of (R) -2-chloro-1-oxiranylmethyl-4-nitro-1H-imidazole was added thereto, and the mixture was stirred at 70 to 80 ° C. for 20 minutes. After cooling to room temperature, water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The combined organic layer was washed with water and saturated brine and then dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane: ethyl acetate = 9: 1 → 6: 4). Recrystallization from a dichloromethane-ethyl acetate mixed solvent and light yellow powdery crystals of (R) -6-nitro-2- {4- [4- (4-trifluoromethoxybenzyloxy) piperidin-1-yl] phenoxymethyl} 0.99 g (14.8%) of -2,3-dihydroimidazo [2,1-b] oxazole was obtained.
Melting point: 188.3-189.4 ° C.

Example 3363
(R) -2-Methyl-6-nitro-2- [4- {4- [2- (4-trifluoromethoxyphenyl) ethyl] piperidin-1-yl} phenoxymethyl] -2,3-dihydroimidazo [ Preparation of 2,1-b] oxazole (R) -2-Chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitro-1H-imidazole 1.01 g and 4- {4- [2 1.36 g of-(4-trifluoromethoxyphenyl) ethyl] piperidin-1-yl} phenol was dissolved in DMF (14 ml), 0.18 g of sodium hydride was added, and the mixture was stirred at 50 ° C. for 1 hour. After cooling to room temperature, water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The combined organic layer was washed with water and saturated brine and then dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane: ethyl acetate = 9: 1 → 8: 2). Recrystallization from a mixed solvent of dichloromethane-ethyl acetate-diisopropyl ether, and light yellow powdery crystals of (R) -2-methyl-6-nitro-2- [4- {4- [2- (4-trifluoromethoxyphenyl)] There were obtained 0.70 g (34.4%) of ethyl] piperidin-1-yl} phenoxymethyl] -2,3-dihydroimidazo [2,1-b] oxazole.
Melting point: 239.4-241.3 ° C.

Example 3364
(R) -2-Methyl-6-nitro-2- {6- [4- (4-trifluoromethoxyphenoxy) piperidin-1-yl] pyridin-3-yloxymethyl} -2,3-dihydroimidazo [ Preparation of 2,1-b] oxazole 0.51 g of (R) -2-chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitro-1H-imidazole and 3-hydroxy-6- [ 0.67 g of 4- (4-trifluoromethoxyphenoxy) piperidin-1-yl] pyridine was dissolved in DMF (6.7 ml), 91 mg of sodium hydride was added, and the mixture was stirred at 50 ° C. for 1 hour. After cooling to room temperature, water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The combined organic layer was washed with water and saturated brine and then dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane: ethyl acetate = 9: 1 → 8: 2). Recrystallization from a dichloromethane-ethyl acetate-diisopropyl ether mixed solvent and light yellow powdery crystals of (R) -2-methyl-6-nitro-2- {6- [4- (4-trifluoromethoxyphenoxy) piperidine-1 -Yl] pyridin-3-yloxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole 296 mg (29.1%) were obtained.
Melting point: 185.9-186.7 ° C.

Example 3365
Preparation of (R) -6-Nitro-2- {4- [4- (4-trifluoromethoxybenzyl) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole 0.72 g of (R) -2-chloro-1-oxiranylmethyl-4-nitro-1H-imidazole and 1.00 g of 4- [4- (4-trifluoromethoxybenzyl) piperidin-1-yl] phenol The mixture was dissolved in DMF (10 ml), 0.14 g of sodium hydride was added, and the mixture was stirred at 50 ° C. for 1 hour. After cooling to room temperature, water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The combined organic layer was washed with water and saturated brine and then dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane: ethyl acetate = 9: 1 → 7: 3). Recrystallization from a mixed solvent of dichloromethane-ethyl acetate-diisopropyl ether and light yellow powdery crystals of (R) -6-nitro-2- {4- [4- (4-trifluoromethoxybenzyl) piperidin-1-yl] phenoxy 0.20 g (13.7%) of methyl} -2,3-dihydroimidazo [2,1-b] oxazole was obtained.
Melting point: 160.5-164.0 ° C.

Example 3366
(R) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethoxyphenyl) -1,4-diazepan-1-yl] phenoxymethyl} -2,3-dihydroimidazo [ Preparation of 2,1-b] oxazole (R) -2-Chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitro-1H-imidazole 2.21 g and 4- [4- (4) 2.86 g of -trifluoromethoxyphenyl) -1,4-diazepan-1-yl] phenol was dissolved in DMF (29 ml), 0.39 g of sodium hydride was added, and the mixture was stirred at 50 ° C for 1 hour. After cooling to room temperature, water was added to the reaction solution, and extracted with dichloromethane. The combined organic layer was washed with water and brine and concentrated. The residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 1: 3 → ethyl acetate). Recrystallized from isopropyl alcohol, and (R) -2-methyl-6-nitro-2- {4- [4- (4-trifluoromethoxyphenyl) -1,4-diazepan-1-yl] phenoxy of red powder 720 mg (16.6%) of methyl} -2,3-dihydroimidazo [2,1-b] oxazole were obtained.
Melting point: 134.0-137.9 ° C.

Example 3367
(R) -2-Methyl-2- [4- {4- [N-methyl-N- (2-fluoro-4-trifluoromethylbenzyl) amino] piperidin-1-yl} phenoxymethyl] -6-nitro Preparation of -2,3-Dihydroimidazo [2,1-b] oxazole (R) -2-Methyl-2- [4- {4- [N-methyl-N-tert-butoxycarbonylamino] piperidine- 1 0.80 g of [i] phenoxymethyl] -6-nitro-2,3-dihydroimidazo [2,1-b] oxazole was dissolved in 2 ml of trifluoroacetic acid and 2 ml of dichloromethane and stirred at room temperature for 15 hours. The reaction solution was concentrated under reduced pressure, and 2 ml each of dichloromethane and triethylamine were added. After stirring for 5 minutes at room temperature, the solution was concentrated under reduced pressure. The residue was dissolved in 8 ml of dichloroethane, 0.63 g of 2-fluoro-4-trifluoromethylbenzaldehyde and 0.70 g of sodium triacetoxyborohydride were added under ice-cooling, and the mixture was warmed to room temperature and stirred for 24 hours. The reaction solution was added with aqueous potassium carbonate solution and dichloromethane, stirred, and extracted with dichloromethane. The organic layer was dried over magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane: methanol = 9: 1). Crystallization was performed from ethyl acetate to give pale yellow powder of (R) -2-methyl-2- [4- {4- [N-methyl-N- (2-fluoro-4-trifluoromethylbenzyl) amino] piperidine. There were obtained 0.48 g (yield 51.8%) of -1-yl} phenoxymethyl] -6-nitro-2,3-dihydroimidazo [2,1-b] oxazole.
Melting point: 197.5-199.2 ° C.

Example 3368
(R) -2-Methyl-2- [4- {4- [N-methyl-N- (2-trifluoromethylbenzyl) amino] piperidin-1-yl} phenoxymethyl] -6-nitro-2,3 Preparation of -dihydroimidazo [2,1-b] oxazole (R) -2-methyl-2- [4- {4- [N-methyl-N-tert-butoxycarbonylamino] piperidin-1-yl} phenoxymethyl 0.80 g of -6-nitro-2,3-dihydroimidazo [2,1-b] oxazole was dissolved in 2 ml of trifluoroacetic acid and 2 ml of dichloromethane and stirred at room temperature for 15 hours. The reaction solution was concentrated under reduced pressure, and 2 ml each of dichloromethane and triethylamine were added. After stirring for 5 minutes at room temperature, the solution was concentrated under reduced pressure. The residue was dissolved in 8 ml of dichloroethane, 0.57 g of 2-trifluoromethylbenzaldehyde and 0.70 g of sodium triacetoxyborohydride were added under ice-cooling, and the mixture was warmed to room temperature and stirred for 24 hours. The reaction solution was added with aqueous potassium carbonate solution and dichloromethane, stirred, and extracted with dichloromethane. The organic layer was dried over magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane: methanol = 9: 1). Crystallization was performed from ethyl acetate to give pale yellow powder of (R) -2-methyl-2- [4- {4- [N-methyl-N- (2-fluoro-4-trifluoromethylbenzyl) amino] piperidine. There were obtained 0.47 g (yield 52.4%) of -1-yl} phenoxymethyl] -6-nitro-2,3-dihydroimidazo [2,1-b] oxazole.
Melting point: 189.6-190.2 ° C.

Example 3369
(R) -2-Methyl-2- [4- {4- [N-methyl-N- (3,5-bistrifluoromethylbenzyl) amino] piperidin-1-yl} phenoxymethyl] -6-nitro-2 Of (R) -2-methyl-2- [4- {4- [N-methyl-N-tert-butoxycarbonylamino] piperidin-1-yl}, 3-dihydroimidazo [2,1-b] oxazole 0.80 g of phenoxymethyl] -6-nitro-2,3-dihydroimidazo [2,1-b] oxazole was dissolved in 2 ml of trifluoroacetic acid and 2 ml of dichloromethane and stirred at room temperature for 15 hours. The reaction solution was concentrated under reduced pressure, and 2 ml each of dichloromethane and triethylamine were added. After stirring for 5 minutes at room temperature, the solution was concentrated under reduced pressure. The residue was dissolved in 8 ml of dichloroethane, 0.79 g of 3,5-bistrifluoromethylbenzaldehyde and 0.70 g of sodium triacetoxyborohydride were added under ice-cooling, and the mixture was warmed to room temperature and stirred for 19 hours. The reaction solution was added with aqueous potassium carbonate solution and dichloromethane, stirred, and extracted with dichloromethane. The organic layer was dried over magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane: methanol = 9: 1). Crystallization was performed from ethyl acetate, and pale yellow powder of (R) -2-methyl-2- [4- {4- [N-methyl-N- (3,5-bistrifluoromethylbenzyl) amino] piperidine-1 was obtained. -Yl} phenoxymethyl] -6-nitro-2,3-dihydroimidazo [2,1-b] oxazole 0.55 g (yield 54.9%) was obtained.
Melting point: 193.8-195.3 ° C.

Example 3370
(R) -2-Methyl-6-nitro-2- {4- [4- (3-trifluoromethoxybenzyl) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b Preparation of] oxazole 1.21 g of (R) -2-chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitro-1H-imidazole and 4- [4- (3-trifluoromethoxybenzyl] 1.56 g of piperidin-1-yl] phenol was dissolved in DMF (16 ml), 0.21 g of sodium hydride was added, and the mixture was stirred at 50 ° C. for 1 hour. After cooling to room temperature, water was added to the reaction solution, and extracted with dichloromethane. The combined organic layer was washed with water and saturated brine and then dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane: ethyl acetate = 9: 1 → 8: 2). Recrystallization from a dichloromethane-ethyl acetate-diisopropyl ether mixed solvent and light yellow powdery crystals of (R) -2-methyl-6-nitro-2- {4- [4- (3-trifluoromethoxybenzyl) piperidine-1 -Yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole 0.80 g (33.8%) was obtained.
Melting point: 187.4-189.8 ° C.

Example 3371
(R) -2-Methyl-2- [4- {4- [N-methyl-N- (5-chlorobenzofuran-2-ylmethyl) amino] piperidin-1-yl} phenoxymethyl] -6-nitro-2 Of (R) -2-methyl-2- [4- {4- [N-methyl-N-tert-butoxycarbonylamino] piperidin-1-yl}, 3-dihydroimidazo [2,1-b] oxazole 0.80 g of phenoxymethyl] -6-nitro-2,3-dihydroimidazo [2,1-b] oxazole was dissolved in 2 ml of trifluoroacetic acid and 2 ml of dichloromethane and stirred at room temperature for 15 hours. The reaction solution was concentrated under reduced pressure, and 2 ml each of dichloromethane and triethylamine were added. After stirring for 5 minutes at room temperature, the solution was concentrated under reduced pressure. The residue was dissolved in 8 ml of dichloroethane, 0.59 g of 5-chlorobenzofuran-2-carbaldehyde and 0.70 g of sodium triacetoxyborohydride were added under ice-cooling, and the mixture was warmed to room temperature and stirred for 22 hours. The reaction solution was added with aqueous potassium carbonate solution and dichloromethane, stirred, and extracted with dichloromethane. The organic layer was dried over magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane: methanol = 9: 1). Crystallization from acetone was carried out, and yellow powder of (R) -2-methyl-2- [4- {4- [N-methyl-N- (5-chlorobenzofuran-2-ylmethyl) amino] piperidin-1-yl } Phenoxymethyl] -6-nitro-2,3-dihydroimidazo [2,1-b] oxazole 0.65 g (yield 66.5%) was obtained.
Melting point: 207.4-210.0 ° C.

Example 3372
(R) -2-Methyl-6-nitro-2- {6- [4- (4-trifluoromethoxybenzyl) piperidin-1-yl] pyridin-3-yloxymethyl} -2,3-dihydroimidazo [ Preparation of 2,1-b] oxazole (R) -2-Chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitro-1H-imidazole 2.63 g and 3-hydroxy-6- [ 3.41 g of 4- (4-trifluoromethoxybenzyl) piperidin-1-yl] pyridine was dissolved in DMF (6.7 ml), 0.46 g of sodium hydride was added, and the mixture was stirred at 50 ° C. for 1.5 hours . After cooling to room temperature, water was added to the reaction solution, and extracted with dichloromethane. The combined organic layer was washed with water and saturated brine and then dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane: ethyl acetate = 9: 1 → 6: 4). Recrystallization from a mixed solvent of ethyl acetate-diisopropyl ether, pale yellow powdery crystals of (R) -2-methyl-6-nitro-2- {6- [4- (4-trifluoromethoxybenzyl) piperidin-1-yl 1.46 g (28.3%) of pyridin-3-yloxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole were obtained.
Melting point: 200.1-202.9 ° C.

Example 3373
(R) -6-nitro-2- [4- {4- [2- (4-trifluoromethoxyphenyl) ethyl] piperidin-1-yl} phenoxymethyl] -2,3-dihydroimidazo [2,1- b) Preparation of oxazole 0.75 g of (R) -2-chloro-1-oxiranylmethyl-4-nitro-1H-imidazole and 4- {4- [2- (4-trifluoromethoxyphenyl) ethyl] piperidine 1.07 g of -1-yl} phenol was dissolved in DMF (11 ml), 0.14 g of sodium hydride was added, and the mixture was stirred at 50 ° C. for 1 hour. After cooling to room temperature, water was added to the reaction solution, and extracted with dichloromethane. The combined organic layer was washed with water and saturated brine and then dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (dichloromethane: ethyl acetate = 9: 1 → 6: 4). Recrystallization from a dichloromethane-diisopropyl ether mixed solvent and light yellow powdery crystals of (R) -6-nitro-2- [4- {4- [2- (4-trifluoromethoxyphenyl) ethyl] piperidin-1-yl } Phenoxymethyl] -2,3-dihydroimidazo [2,1-b] oxazole 0.31 g (19.8%) was obtained.
Melting point: 208.9-211.7 ° C.

Example 3374
(R) -2-Methyl-2- [4- {4- [N-methyl-N- (4-trifluoromethoxycinnamyl) amino] piperidin-1-yl} phenoxymethyl] -6-nitro-2, Preparation of 3-Dihydroimidazo [2,1-b] oxazole (R) -2-Methyl-2- [4- {4- [N-methyl-N-tert-butoxycarbonylamino] piperidin-1-yl} phenoxy 2.76 g of methyl] -6-nitro-2,3-dihydroimidazo [2,1-b] oxazole were dissolved in 5 ml of trifluoroacetic acid and 10 ml of dichloromethane and stirred for 0.5 hours at room temperature. The reaction solution was concentrated under reduced pressure, and 10 ml each of dichloromethane and N, N-dimethylethylamine were added. After stirring for 10 minutes at room temperature, the solution was concentrated under reduced pressure. The residue was dissolved in 30 ml of dichloroethane, and 1.43 g of 4-trifluoromethoxycinnaldehyde and 1.78 g of sodium triacetoxyborohydride were added under ice-cooling, and the mixture was warmed to room temperature and stirred overnight. The reaction solution was added with aqueous potassium carbonate solution and dichloromethane, stirred, and extracted with dichloromethane. The organic layer was dried over magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane: acetone = 5: 1 → 1: 1). Recrystallization from aqueous acetone gave pale yellow powder of (R) -2-methyl-2- [4- {4- [N-methyl-N- (4-trifluoromethoxycinnamyl) amino] piperidine-1- 1.97 g (yield 58.9%) of [i] phenoxymethyl] -6-nitro-2,3-dihydroimidazo [2,1-b] oxazole were obtained.
Melting point: 213.0-214.9 ° C.

Example 3375
(R) -2- {4- [4- (3,4-dichlorocinnamyl) piperazin-1-yl] phenoxymethyl} -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-] b) Preparation of oxazole (R) -2-Methyl-2- [4- (4-tert-butoxycarbonylpiperazin-1-yl) phenoxymethyl] -6-nitro-2,3-dihydroimidazo [2,1- b) 2.76 g of oxazole was dissolved in 5 ml of trifluoroacetic acid and 10 ml of dichloromethane and stirred at room temperature for 0.5 hours. The reaction solution was concentrated under reduced pressure, and 10 ml each of dichloromethane and N, N-dimethylethylamine were added. After stirring for 5 minutes at room temperature, the solution was concentrated under reduced pressure. The residue was dissolved in 30 ml of dichloroethane, 1.33 g of 3,4-dichlorocinnamyl aldehyde and 1.78 g of sodium triacetoxyborohydride were added and stirred overnight at room temperature. The reaction solution was added with aqueous potassium carbonate solution and dichloromethane, stirred, and extracted with dichloromethane. The organic layer was dried over magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane: acetone = 5: 1 → 1: 1). The crystallization is carried out from a dichloromethane-ethyl acetate mixed solvent, and (R) -2- {4- [4- (3,4-dichlorocinnamyl) piperazin-1-yl] phenoxymethyl} -2-methyl as pale yellow powder. 2.243 g (yield 68.7%) of -6-nitro-2,3-dihydroimidazo [2,1-b] oxazole was obtained.
Melting point: 204.7-206.4 ° C.

Example 3376
(R) -2-Methyl-2- [4- {N-methyl-N- [1- (4-trifluoromethoxyphenyl) piperidin-4-ylmethyl] amino} phenoxymethyl] -6-nitro-2,3 Preparation of -dihydroimidazo [2,1-b] oxazole (R) -2-chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitro-1H-imidazole 0.408 g and 4- { Dissolve 0.57 g of N-methyl-N- [1- (4-trifluoromethoxyphenyl) piperidin-4-ylmethyl] amino} phenol in 6 ml of DMF, add 72 mg of sodium hydride, and keep at 50-60 ° C. for 2 hours It stirred. After cooling to room temperature, water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The combined organic layer was washed with water and saturated brine and then dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 1: 3 → dichloromethane: ethyl acetate = 1: 1). Recrystallized from aqueous acetone, orange powder crystals of (R) -2-methyl-2- [4- {N-methyl-N- [1- (4-trifluoromethoxyphenyl) piperidin-4-ylmethyl] amino} 0.130 g (yield 15.4%) of phenoxymethyl] -6-nitro-2,3-dihydroimidazo [2,1-b] oxazole was obtained.
Melting point: 172.5-175.2 ° C.

Example 3377
(R) -2-Methyl-2- [4- {N-methyl-N- [1- (4-trifluoromethoxyphenyl) piperidin-4-yl] amino} phenoxymethyl] -6-nitro-2,3 Preparation of -dihydroimidazo [2,1-b] oxazole (R) -2-chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitro-1H-imidazole 0.131 g and 4- { 0.177 g of N-methyl-N- [1- (4-trifluoromethoxyphenyl) piperidin-4-yl] amino} phenol is dissolved in 4 ml of DMF, 23 mg of sodium hydride is added, and the reaction is carried out at 50 to 60 ° C. for 2 hours It stirred. After cooling to room temperature, water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The combined organic layer was washed with water and saturated brine and then dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 1: 3 → dichloromethane: ethyl acetate = 1: 1). Recrystallized from aqueous acetone, pale yellow powdery crystals of (R) -2-methyl-2- [4- {N-methyl-N- [1- (4-trifluoromethoxyphenyl) piperidin-4-yl] amino } Phenoxymethyl] -6-nitro-2,3-dihydroimidazo [2,1-b] oxazole 93 mg (yield 35%) was obtained.
Melting point: 137.9-139.2 ° C.

Example 3378
(R) -2-Methyl-6-nitro-2- [4- {1- [2- (4-trifluoromethylphenyl) thiazol-4-ylmethyl] piperidin-4-yl} phenoxymethyl] -2,3 Preparation of -dihydroimidazo [2,1-b] oxazole (R) -2-Methyl-6-nitro-2- [4- (1-tert-butoxycarbonylpiperidin-4-yl) phenoxymethyl] -2,3 0.300 g of -dihydroimidazo [2,1-b] oxazole was added to 1 ml of trifluoroacetic acid and 1 ml of dichloromethane and stirred for 1 hour at room temperature. The reaction solution was concentrated under reduced pressure, the residue was dissolved in 1 ml of dichloromethane, 1 ml of triethylamine was added, and the mixture was stirred at room temperature for 5 minutes and then concentrated under reduced pressure. The residue is dissolved in 5 ml of methanol, 0.219 g of 2- (4-trifluoromethylphenyl) thiazole-4-carbaldehyde, 82 mg of sodium cyanotrihydroborate and 0.5 ml of acetic acid are added under ice-cooling, and the solution is cooled to room temperature. Stir for 3 days. Saturated aqueous sodium hydrogen carbonate solution was added and stirred, extracted with ethyl acetate and washed with saturated brine. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane: acetone = 3: 1 → dichloromethane: methanol = 20: 1). The white powder of (R) -2-methyl-6-nitro-2- [4- {1- [2- (4-trifluoromethylphenyl) thiazol-4-ylmethyl] piperidine was recrystallized from water-containing acetone. There were obtained 65 mg (16.6% yield) of 4-yl} phenoxymethyl] -2,3-dihydroimidazo [2,1-b] oxazole.
Melting point: 194.6-196.4 ° C.

Example 3379
(R) -2-Methyl-6-nitro-2- {4- [1- (4-trifluoromethylcinnamyl) piperidin-4-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-] b) Preparation of oxazole (R) -2-Methyl-6-nitro-2- [4- (1-tert-butoxycarbonylpiperidin-4-yl) phenoxymethyl] -2,3-dihydroimidazo [2,1- b) 0.300 g of oxazole was added to 1 ml of trifluoroacetic acid and 1 ml of dichloromethane, and stirred at room temperature for 1 hour. The reaction solution was concentrated under reduced pressure, the residue was dissolved in 1 ml of dichloromethane, 1 ml of triethylamine was added, and the mixture was stirred at room temperature for 5 minutes and then concentrated under reduced pressure. The residue was dissolved in 5 ml of methanol, and 0.170 g of 4-trifluoromethylcinnaldehyde, 82 mg of sodium cyanotrihydroborate and 0.5 ml of acetic acid were added under ice-cooling, and the mixture was stirred at room temperature for 3 days. Saturated aqueous sodium hydrogen carbonate solution was added and stirred, extracted with ethyl acetate and washed with saturated brine. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane: acetone = 3: 1 → dichloromethane: methanol = 20: 1). Recrystallization from aqueous acetone, white powder of ((R) -2-methyl-6-nitro-2- {4- [1- (4-trifluoromethylcinnamyl) piperidin-4-yl] phenoxymethyl} 66 mg (yield 18.6%) of -2,3-dihydroimidazo [2,1-b] oxazole were obtained.
Melting point: 185.9-187.1C.

Example 3380
(R) -2-Methyl-6-nitro-2- [4-{4- [2- (4-trifluoromethoxyphenoxy) ethyl] piperazin-1-yl} phenoxymethyl] -2,3-dihydroimidazo Preparation of [2,1-b] oxazole (R) -2-Methyl-6-nitro-2- [4- (4-tert-butoxycarbonylpiperazin-1-yl) phenoxymethyl] -2,3-dihydroimidazo 0.300 g of [2,1-b] oxazole was added to 3 ml of trifluoroacetic acid and 3 ml of dichloromethane, and stirred at room temperature for 2 hours. The reaction solution was concentrated under reduced pressure, the residue was dissolved in 3 ml of dichloromethane, 3 ml of triethylamine was added, and the mixture was stirred at room temperature for 10 minutes and then concentrated under reduced pressure. The residue was dissolved in 5 ml of methanol, and 0.170 g of 4-trifluoromethoxyphenoxyacetaldehyde, 82 mg of sodium cyanotrihydroborate and 0.1 ml of acetic acid were added under ice-cooling, and the mixture was stirred overnight at room temperature. Saturated aqueous sodium hydrogen carbonate solution was added and stirred, extracted with ethyl acetate and washed with saturated brine. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane: acetone = 3: 1 → dichloromethane: methanol = 20: 1). Recrystallization from aqueous acetone, white powder of ((R) -2-methyl-6-nitro-2- {4- [1- (4-trifluoromethylcinnamyl) piperidin-4-yl] phenoxymethyl} 157 mg (42.7% yield) of -2,3-dihydroimidazo [2,1-b] oxazole were obtained.
Melting point: 194.8-195.6 ° C.

Example 3381
(R) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethylcinnamyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-] b) Preparation of oxazole (R) -2-Methyl-6-nitro-2- [4- (4-tert-butoxycarbonylpiperazin-1-yl) phenoxymethyl] -2,3-dihydroimidazo [2,1- b) 0.300 g of oxazole was added to 3 ml of trifluoroacetic acid and 3 ml of dichloromethane, and stirred at room temperature for 1 hour. The reaction solution was concentrated under reduced pressure, the residue was dissolved in 3 ml of dichloromethane, 3 ml of triethylamine was added, and the mixture was stirred at room temperature for 5 minutes and then concentrated under reduced pressure. The residue was dissolved in 5 ml of methanol, 0.170 g of 4-trifluoromethylcinnaldehyde, 82 mg of sodium cyanotrihydroborate and 0.1 ml of acetic acid were added under ice-cooling, and the mixture was stirred at room temperature for 3 days. Saturated aqueous sodium hydrogen carbonate solution was added and stirred, extracted with ethyl acetate and washed with saturated brine. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane: acetone = 3: 1 → dichloromethane: methanol = 20: 1). Recrystallization from water-containing acetone, pale yellow powder of (R) -2-methyl-6-nitro-2- {4- [4- (4-trifluoromethylcinnamyl) piperazin-1-yl] phenoxymethyl} 66 mg (yield 18.6%) of -2,3-dihydroimidazo [2,1-b] oxazole were obtained.
Melting point: 199.7-202.0 ° C.

Example 3382
(R) -2-Methyl-6-nitro-2- [4- {4- [2- (4-trifluoromethylphenyl) thiazol-4-ylmethyl] piperazin-1-yl} phenoxymethyl] -2,3 Preparation of -dihydroimidazo [2,1-b] oxazole (R) -2-Methyl-6-nitro-2- [4- (4-tert-butoxycarbonylpiperazin-1-yl) phenoxymethyl] -2,3 0.300 g of -dihydroimidazo [2,1-b] oxazole was added to 3 ml of trifluoroacetic acid and 3 ml of dichloromethane and stirred for 2 hours at room temperature. The reaction solution was concentrated under reduced pressure, the residue was dissolved in 3 ml of dichloromethane, 3 ml of triethylamine was added, and the mixture was stirred at room temperature for 10 minutes and then concentrated under reduced pressure. The residue is dissolved in 5 ml of methanol, and 0.218 g of 2- (4-trifluoromethylphenyl) thiazole-4-carbaldehyde, 82 mg of sodium cyanotrihydroborate and 0.5 ml of acetic acid are added under ice-cooling, and the solution is cooled to room temperature. Stir overnight. Saturated aqueous sodium hydrogen carbonate solution was added and stirred, extracted with ethyl acetate and washed with saturated brine. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane: acetone = 3: 1 → dichloromethane: methanol = 20: 1). The white powder of (R) -2-methyl-6-nitro-2- [4- {4- [2- (4-trifluoromethylphenyl) thiazol-4-ylmethyl] piperazine was recrystallized from water-containing acetone. There were obtained 0.167 g (yield 42.6%) of 1-yl} phenoxymethyl] -2,3-dihydroimidazo [2,1-b] oxazole.
Melting point: 210.0-212.1 ° C.

Example 3383
(R) -2- [4- {4- [N- (4-chlorophenyl) -N-methylamino] piperidin-1-yl} phenoxymethyl] -2-methyl-6-nitro-2,3-dihydroimidazo Preparation of [2,1-b] oxazole Dissolve 776 mg of 4- {4- [N- (4-chlorophenyl) -N-methylamino] piperidin-1-yl} phenol in 10 ml of DMF, add 108 mg of sodium hydride and add 70 Stirred at -80 ° C for 10 minutes. The reaction solution was ice-cooled, 746 mg of (R) -2-chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitro-1H-imidazole was added, and the mixture was stirred at 70-80 ° C. for 20 minutes. . After allowing to cool to room temperature, ice water was added to the reaction liquid and stirred, and the generated insoluble matter was collected by filtration. The filtrate was dissolved in dichloromethane, washed with saturated brine and dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (dichloromethane: ethyl acetate = 10: 1). Recrystallization from a mixed solvent of dichloromethane and ethyl acetate and white powder crystals of (R) -2- [4- {4- [N- (4-chlorophenyl) -N-methylamino] piperidin-1-yl} phenoxymethyl] 485 mg (39.8% yield) of -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole were obtained.
Melting point: 173.7-175.1 ° C.

Example 3384
(R) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethylphenoxymethyl) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-] b) Preparation of oxazole (R) -2-chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitro-1H-imidazole 574 mg and 4- [4- (4-trifluoromethylphenoxymethyl) 844 mg of (piperidine-1-yl) phenol was heated to 140 ° C. and stirred for 4 hours. After allowed to cool to room temperature, the residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 1: 3), and after concentration, the residue was dissolved in 10 ml of DMF. Under ice-cooling, 174 mg of sodium tert-butoxide was added, and the mixture was stirred at room temperature for 2 hours. The solvent was distilled off under reduced pressure, and 100 ml of acetone and 10 ml of silica gel were added to the residue and concentrated. The residue is purified by silica gel column chromatography (dichloromethane: ethyl acetate = 10: 1 to 1: 1) and recrystallized from a dichloromethane-ethyl acetate mixed solvent to give (R) -2-methyl-6-nitro- as a white powder. 1.15 g (yield 38%) of 2- {4- [4- (4-trifluoromethylphenoxymethyl) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole )Obtained.
Melting point: 223.2-225.2 ° C (decomposition).

Example 3385
(R) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethylbenzyloxymethyl) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1 -B] Preparation of oxazole Dissolve 2.48 g of 4- [4- (4-trifluoromethylbenzyloxymethyl) piperidin-1-yl] phenol in 30 ml of DMF, and add 312 mg of sodium hydride at 70-80 ° C. Stirred for a minute. The reaction solution is ice-cooled, and 2.07 g of (R) -2-chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitro-1H-imidazole is added and the mixture is heated at 70-80 ° C. for 20 minutes. It stirred. After allowing to cool to room temperature, ice water was added to the reaction liquid and stirred, and the generated insoluble matter was collected by filtration. The filtrate was dissolved in dichloromethane, washed with saturated brine and dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane: ethyl acetate = 10: 1). Recrystallized from ethyl acetate, white powder crystals of (R) -2-methyl-6-nitro-2- {4- [4- (4-trifluoromethylbenzyloxymethyl) piperidin-1-yl] phenoxymethyl} 1.66 g (yield 44.7%) of -2,3-dihydroimidazo [2,1-b] oxazole were obtained.
Melting point: 172.3-172.9 ° C.

Example 3386
(R) -2-Methyl-6-nitro-2- {4- [4- (4-chloromethylphenoxymethyl) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b Preparation of Oxazole 1.09 g of 4- [4- (4-chloromethylphenoxymethyl) piperidin-1-yl] phenol was dissolved in 20 ml of DMF, and 158 mg of sodium hydride was added thereto and stirred at 70-80 ° C. for 20 minutes. The reaction solution was ice-cooled, 1.04 g of (R) -2-chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitro-1H-imidazole was added, and the mixture was stirred at 60 ° C. for 30 minutes. . After allowing to cool to room temperature, ice water was added to the reaction liquid and stirred, and the generated insoluble matter was collected by filtration. The filtrate is dissolved in dichloromethane, washed with saturated brine and dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane: methanol = 20: 1). Recrystallization from ethyl acetate and pale yellow powdery crystals of (R) -2-methyl-6-nitro-2- {4- [4- (4-chloromethylphenoxymethyl) piperidin-1-yl] phenoxymethyl}- 744 mg (43.5% yield) of 2,3-dihydroimidazo [2,1-b] oxazole were obtained.
Melting point: 140.4-141.7 ° C.

Example 3387
(R) -6-Nitro-2- {4- [4- (4-trifluoromethylphenoxymethyl) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole Preparation 1.22 grams of 4- [4- (4-trifluoromethylphenoxymethyl) piperidin-1-yl] phenol was dissolved in 15 ml DMF, 196 mg sodium hydride was added and stirred at 70-80 ° C. for 30 minutes. The reaction solution was ice-cooled, 1.57 g of (R) -2-chloro-1-oxiranylmethyl-4-nitro-1H-imidazole was added, and the mixture was stirred at 80 ° C. for 20 minutes. After allowing to cool to room temperature, ice water was added to the reaction liquid and stirred, and the generated insoluble matter was collected by filtration. The filtrate was dissolved in dichloromethane, washed with saturated brine and dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane: methanol = 20: 1). Recrystallization from ethyl acetate and white powder crystals of (R) -6-nitro-2- {4- [4- (4-trifluoromethylphenoxymethyl) piperidin-1-yl] phenoxymethyl} -2,3- 505 mg (yield 22.1%) of dihydroimidazo [2,1-b] oxazole was obtained.
Melting point: 175.0-180 ° C.

Example 3388
(R) -2- {4 '-[4- (4-chlorobenzyl) piperazin-1-yl] biphenyl-4-yloxymethyl} -2-methyl-6-nitro-2,3-dihydroimidazo [2] Preparation of 1,1-b] oxazole (R) -2-Methyl-2- [4 '-(4-tert-butoxycarbonylpiperazin-1-yl) biphenyl-4-yloxymethyl] -6-nitro-2, 850 mg of 3-dihydroimidazo [2,1-b] oxazole was dissolved in 10 ml of trifluoroacetic acid and 5 ml of dichloromethane and stirred overnight at room temperature. The reaction solution was concentrated under reduced pressure, and 6 ml each of dichloromethane and triethylamine were added. After stirring for 5 minutes at room temperature, the solution was concentrated under reduced pressure. The residue was dissolved in 10 ml of DMF, and 444.2 mg of 4-chlorobenzaldehyde and 672 mg of sodium triacetoxyborohydride were added under ice-cooling, and the mixture was stirred overnight at room temperature. Aqueous sodium hydrogen carbonate solution and ethyl acetate were added to the reaction solution and the mixture was stirred, and the resulting insoluble matter was collected by filtration. After washing with water and ethyl acetate and drying, a pale yellow powder of (R) -2- {4 '-[4- (4-chlorobenzyl) piperazin-1-yl] biphenyl-4-yloxymethyl} -2 There were obtained 730 mg (yield 51.8%) of -methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole.
Melting point: 247.8-248.5 ° C. (decomposition).

Example 3389
(R) -2-Methyl-6-nitro-2- {4 '-[4- (4-trifluoromethylbenzyl) piperazin-1-yl] biphenyl-4-yloxymethyl} -2,3-dihydroimidazo Preparation of [2,1-b] oxazole (R) -2-Methyl-2- [4 '-(4-tert-butoxycarbonylpiperazin-1-yl) biphenyl-4-yloxymethyl] -6-nitro- 790 mg of 2,3-dihydroimidazo [2,1-b] oxazole were dissolved in 10 ml of trifluoroacetic acid and 5 ml of dichloromethane and stirred overnight at room temperature. The reaction solution was concentrated under reduced pressure, and 6 ml each of dichloromethane and triethylamine were added. After stirring for 5 minutes at room temperature, the solution was concentrated under reduced pressure. The residue was dissolved in 15 ml of DMF, and 0.4 ml of 4-trifluoromethylbenzaldehyde and 625 mg of sodium triacetoxyborohydride were added under ice-cooling, and the mixture was stirred overnight at room temperature. Water was added to the reaction solution and stirred, and the resulting insoluble matter was collected by filtration. After washing with water, the filtrate was dissolved in dichloromethane, washed with saturated brine and dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane: methanol = 20: 1). Recrystallization from a mixed solvent of dichloromethane and ethyl acetate gave (R) -2-methyl-6-nitro-2- {4 '-[4- (4-trifluoromethoxybenzyl) piperazin-1-yl as a pale yellow powder. 585 mg (yield 60.5%) of biphenyl-4-yloxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole was obtained.
Melting point: 247.7-248.4 ° C (decomposition).

Example 3390
(R) -2-Methyl-6-nitro-2- [4- {4- [2- (4-trifluoromethoxybenzyloxy) ethyl] piperidin-1-yl} phenoxymethyl] -2,3-dihydroimidazo Preparation of [2,1-b] oxazole (R) -2-Chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitro-1H-imidazole 959 mg and 4- {4- [2-] 1.24 g of (4-trifluoromethoxybenzyloxy) ethyl] piperidin-1-yl} phenol was dissolved in 20 ml of DMF, 176 mg of sodium hydride was added, and the mixture was stirred at 55 ° C. for 1 hour. After allowing to cool to room temperature, ice water was added to the reaction solution, and the mixture was stirred, and the resulting insoluble matter was collected by filtration. The filtrate was dissolved in dichloromethane, washed with saturated brine and dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane: ethyl acetate = 10: 1). Recrystallization from a mixed solvent of dichloromethane and ethyl acetate, and white powder crystals of (R) -2-methyl-6-nitro-2- [4- {4- [2- (4-trifluoromethoxybenzyloxy) ethyl] piperidine There were obtained 562 mg (yield 28.8%) of -1-yl} phenoxymethyl] -2,3-dihydroimidazo [2,1-b] oxazole.
Melting point: 204.8-206.7 ° C.

Example 3391
(R) -2-Methyl-6-nitro-2- [4- {4- [2- (4-trifluoromethylbenzyloxy) ethyl] piperidin-1-yl} phenoxymethyl] -2,3-dihydroimidazo Preparation of [2,1-b] oxazole (R) -2-Chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitro-1H-imidazole 741 mg and 4- {4- [2-] 1.00 g of (4-trifluoromethylbenzyloxy) ethyl] piperidin-1-yl} phenol was dissolved in 10 ml of DMF, 136 mg of sodium hydride was added, and the mixture was stirred at 55 ° C. for 1 hour. After allowing to cool to room temperature, ice water was added to the reaction liquid and stirred, and the generated insoluble matter was collected by filtration. The filtrate was dissolved in dichloromethane, washed with saturated brine and dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane: ethyl acetate = 10: 1). Recrystallization from a dichloromethane-ethyl acetate mixed solvent and white powder crystals of (R) -2-methyl-6-nitro-2- [4- {4- [2- (4-trifluoromethylbenzyloxy) ethyl] piperidine There were obtained 548 mg (yield 37.3%) of -1-yl} phenoxymethyl] -2,3-dihydroimidazo [2,1-b] oxazole.
Melting point: 198.0-199.2 ° C.

Example 3392
(R) -2- [4- {4- [2- (4-chlorobenzyloxy) ethyl] piperidin-1-yl} phenoxymethyl] -2-methyl-6-nitro-2,3-dihydroimidazo [2 (R) -2-Chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitro-1H-imidazole 900 mg and 4- {4- [2- (4) 1.10 g of -chlorobenzyloxy) ethyl] piperidin-1-yl} phenol was dissolved in 10 ml of DMF, 165 mg of sodium hydride was added, and the mixture was stirred at 55 ° C. for 1 hour. After allowing to cool to room temperature, ice water was added to the reaction liquid and stirred, and the generated insoluble matter was collected by filtration. The filtrate was dissolved in dichloromethane, washed with saturated brine and dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane: ethyl acetate = 10: 1). Recrystallization from a dichloromethane-ethyl acetate mixed solvent gives white powder crystals of (R) -2- [4- {4- [2- (4-chlorobenzyloxy) ethyl] piperidin-1-yl} phenoxymethyl] -2 548 mg (yield 37.3%) of -methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole were obtained.
Melting point: 197.6-198.2 ° C.

Example 3393
(R) -2-Methyl-6-nitro-2- (4- [4- {4- [4- (4-trifluoromethoxyphenoxy) piperidin-1-yl] benzyl} piperazin-1-yl] phenoxymethyl Preparation of (2) -2,3-dihydroimidazo [2,1-b] oxazole (R) -2-methyl-2- [4- (4-tert-butoxycarbonylpiperazin-1-yl) phenoxymethyl] -6- 350 mg of nitro-2,3-dihydroimidazo [2,1-b] oxazole were dissolved in 10 ml of trifluoroacetic acid and stirred for 5 hours at room temperature. The reaction solution was concentrated under reduced pressure, and 2 ml each of dichloromethane and triethylamine were added. After stirring for 5 minutes at room temperature, the solution was concentrated under reduced pressure. The residue was dissolved in 10 ml of dichloroethane, 278 mg of 4- [4- (4-trifluoromethoxyphenoxy) piperidin-1-yl] benzaldehyde and 242 mg of sodium triacetoxyborohydride were added under ice-cooling, and the mixture was stirred overnight at room temperature. To the reaction solution was added aqueous sodium hydrogen carbonate solution, and the mixture was extracted with dichloromethane. The extract was washed with saturated brine and dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane: ethyl acetate = 10: 1). Recrystallization from a dichloromethane-diisopropyl ether mixed solvent gave a pale yellow powder of (R) -2-methyl-6-nitro-2- (4- [4- {4- [4- (4-trifluoromethoxyphenoxy)]. There were obtained 295 mg (yield 55%) of piperidin-1-yl] benzyl} piperazin-1-yl] phenoxymethyl) -2,3-dihydroimidazo [2,1-b] oxazole.
Melting point: 198.2-201.4 ° C.

Example 3394
(R) -2- {4 '-[4- (3,4-dichlorobenzyl) piperazin-1-yl] biphenyl-4-yloxymethyl} -2-methyl-6-nitro-2,3-dihydroimidazo Preparation of [2,1-b] oxazole (R) -2-Methyl-2- [4 '-(4-tert-butoxycarbonylpiperazin-1-yl) biphenyl-4-yloxymethyl] -6-nitro- 350 mg of 2,3-dihydroimidazo [2,1-b] oxazole were dissolved in 10 ml of trifluoroacetic acid and stirred for 5 hours at room temperature. The reaction solution was concentrated under reduced pressure, and 2 ml each of dichloromethane and triethylamine were added. After stirring for 5 minutes at room temperature, the solution was concentrated under reduced pressure. The residue was dissolved in 10 ml of dichloroethane, 278 mg of 3,4-dichlorobenzaldehyde and 242 mg of sodium triacetoxyborohydride were added under ice-cooling, and the mixture was stirred overnight at room temperature. Water was added to the reaction solution and stirred, and the generated insoluble matter was collected by filtration. The filtrate was dissolved in dichloromethane, washed with saturated brine and dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue is purified by silica gel column chromatography (dichloromethane: methanol = 20: 1) to give (R) -2- {4 '-[4- (3,4-dichlorobenzyl) piperazin-1-yl] as pale yellow powder. There were obtained 252 mg (yield 41.1%) of biphenyl-4-yloxymethyl} -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole.
Melting point: 222.6-225.1 ° C (decomposition).

Example 3395
(R) -2-Methyl-6-nitro-2- [4- {4- [4- (4-trifluoromethoxyphenoxy) phenylamino] piperidin-1-yl} phenoxymethyl] -2,3-dihydroimidazo Preparation of [2,1-b] oxazole (R) -2-Methyl-6-nitro-2- [4- (4-oxopiperidin-1-yl) phenoxymethyl] -2,3-dihydroimidazo [2,2 To a solution of 1-b] oxazole 400 mg in dichloroethane (10 ml) was added 376 mg 4- (4-trifluoromethoxyphenoxy) aniline and 453 mg sodium triacetoxyborohydride, and the mixture was stirred overnight at room temperature. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with dichloromethane. The organic layer was dried over magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (dichloromethane: methanol = 20: 1). The white powder of (R) -2-methyl-6-nitro-2- [4- {4- [4- (4-trifluoromethoxyphenoxy) phenylamino] piperidine is recrystallized from a dichloromethane-diisopropyl ether mixed solvent. There were obtained 650 mg (83.2% yield) of -1-yl} phenoxymethyl] -2,3-dihydroimidazo [2,1-b] oxazole.
Melting point: 198.6-201.1 ° C. (decomposition).

Example 3396
(R) -2-Methyl-6-nitro-2- (4- [4- {N-methyl-N- [3- (4-trifluoromethoxyphenoxy) propyl] amino} piperidin-1-yl] phenoxymethyl Preparation of (R) -2-Methyl-6-nitro-2- [4- {4- [3- (4-trifluoromethoxyphenoxy) propyl] -2,3-dihydroimidazo [2,1-b] oxazole [Amino] piperidin-1-yl} phenoxymethyl] -2,3-dihydroimidazo [2,1-b] oxazole 237 mg is dissolved in a mixed solvent of 10 ml of dichloromethane and 10 ml of methanol, and 0.15 ml of a 30% aqueous formaldehyde solution, 71.4 mg of sodium hydroborate and 0.01 ml of acetic acid were added, and the mixture was stirred overnight at room temperature. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with dichloromethane. The organic layer was dried over magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (dichloromethane: methanol = 20: 1). Recrystallization from a dichloromethane-diisopropyl ether mixed solvent gave a pale yellow powder of (R) -2-methyl-6-nitro-2- (4- [4- {N-methyl-N- [3- (4-tri) There were obtained 215 mg (yield 88.7%) of fluoromethoxyphenoxy) propyl] amino} piperidin-1-yl] phenoxymethyl) -2,3-dihydroimidazo [2,1-b] oxazole.
Melting point: 167.4-170.2 ° C.

Example 3397
(R) -2- {4- [4- (3,4-dichlorophenylamino) piperidin-1-yl] phenoxymethyl} -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b (R) -2-Chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitro-1H-imidazole 628 mg and 4- [4- (3,4-dichlorophenylamino) piperidine 750 mg of -1-yl] phenol was dissolved in 10 ml of DMF, 117 mg of sodium hydride was added, and the mixture was stirred at 60 ° C. for 20 minutes. After cooling to room temperature, water was added to the reaction solution, and the resulting insoluble matter was collected by filtration. The filtrate was dissolved in dichloromethane, washed with saturated brine and dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane: ethyl acetate = 9: 1 → 8: 2). Recrystallization from a dichloromethane-diisopropyl ether mixed solvent gave pale yellow powdery crystals of (R) -2- {4- [4- (3,4-dichlorophenylamino) piperidin-1-yl] phenoxymethyl} -2-methyl- 441 mg (yield 39%) of 6-nitro-2,3-dihydroimidazo [2,1-b] oxazole were obtained.
Melting point: 146-147.4C.

Example 3398
(R) -2-Methyl-6-nitro-2- (4- [4- {N-methyl-N- [2- (4-trifluoromethoxyphenoxy) ethyl] amino} piperidin-1-yl] phenoxymethyl Preparation of (R) -2-Methyl-6-nitro-2- [4- {4- [2- (4-trifluoromethoxyphenoxy) ethyl] -2,3-dihydroimidazo [2,1-b] oxazole [Amino] piperidin-1-yl} phenoxymethyl] -2,3-dihydroimidazo [2,1-b] oxazole 200 mg is dissolved in a mixed solvent of 2 ml of dichloromethane and 2 ml of methanol, 0.13 ml of a 30% aqueous formaldehyde solution, cyanotritri Sodium hydroborate 65 mg and acetic acid 0.07 ml were added and stirred overnight at room temperature. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with dichloromethane. The organic layer was dried over magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (dichloromethane: methanol = 20: 1). Recrystallization from a dichloromethane-diisopropyl ether mixed solvent gives a white powder of (R) -2-methyl-6-nitro-2- (4- [4- {N-methyl-N- [2- (4-trifluoro) There were obtained 155 mg (yield 75.7%) of methoxyphenoxy) ethyl] amino} piperidin-1-yl] phenoxymethyl) -2,3-dihydroimidazo [2,1-b] oxazole.
Melting point: 185.7-187.7 ° C.

Example 3399
(R) -2-Methyl-6-nitro-2- [4- {4- [4- (4-trifluoromethoxyphenyl) piperazin-1-yl] piperidin-1-yl} phenoxymethyl] -2,3 -Preparation of dihydroimidazo [2,1-b] oxazole (R) -2-Methyl-6-nitro-2- [4- (4-oxopiperidin-1-yl) phenoxymethyl] -2,3-dihydroimidazo 145 mg of 1- (4-trifluoromethoxyphenyl) piperazine, 273 mg of sodium triacetoxyborohydride and 0.061 ml of acetic acid were added to an acetonitrile solution (15 ml) of 200 mg of [2,1-b] oxazole, and stirred at room temperature for 11 days . To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with dichloromethane. The organic layer was dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (dichloromethane: methanol = 20: 1). Recrystallization from isopropyl alcohol gives (R) -2-methyl-6-nitro-2- [4- {4- (4-trifluoromethoxyphenyl) piperazin-1-yl] piperidine as a white powder. 143 mg (yield 44.2%) of 1-yl} phenoxymethyl] -2,3-dihydroimidazo [2,1-b] oxazole were obtained.
Melting point: 279-281 ° C.

Example 3400
(R) -2- {4- [4- (3,5-dichlorophenylamino) piperidin-1-yl] phenoxymethyl} -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b (R) -2-Chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitro-1H-imidazole 1.82 g and 4- [4- (3,5-dichlorophenylamino) 2.02 g of piperidin-1-yl] phenol was dissolved in 20 ml of DMF, 264 mg of sodium hydride was added, and the mixture was stirred at 60 ° C. for 20 minutes. After cooling to room temperature, water and ethyl acetate were added to the reaction solution and the mixture was stirred, and the resulting insoluble matter was collected by filtration. The filtrate was dissolved in dichloromethane, washed with saturated brine and dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane: ethyl acetate = 9: 1 → dichloromethane: methanol = 20: 1). Recrystallization from a mixed solvent of ethyl acetate-diethyl ether, and light yellow powdery crystals of (R) -2- {4- [4- (3,5-dichlorophenylamino) piperidin-1-yl] phenoxymethyl} -2-methyl 1.19 g (yield 38%) of -6-nitro-2,3-dihydroimidazo [2,1-b] oxazole was obtained.
Melting point: 122-124 ° C.

Working Example 3401
(R) -2- [4- {4- [4- (4-chlorophenyl) piperazin-1-yl] piperidin-1-yl} phenoxymethyl] -2-methyl-6-nitro-2,3-dihydroimidazo Preparation of [2,1-b] oxazole To a solution of 290 mg of 1- (4-chlorophenyl) piperazine dihydrochloride (10 ml) was added 10 ml of a 20% aqueous solution of sodium carbonate and the mixture was irradiated with ultrasonic waves. After extraction with dichloromethane and drying over sodium sulfate, the solvent was evaporated under reduced pressure. The residue is dissolved in 15 ml of dichloroethane and (R) -2-methyl-6-nitro-2- [4- (4-oxopiperidin-1-yl) phenoxymethyl] -2,3-dihydroimidazo [2,1- b) 200 mg of oxazole, 341 mg of sodium triacetoxyborohydride and 0.092 ml of acetic acid were added and stirred at room temperature for 24 hours. To the reaction solution was added a 20% aqueous solution of sodium carbonate, and the mixture was concentrated under reduced pressure, water was added to the residue, and the resulting insoluble matter was collected by filtration. The filtrate is washed with water, dried and recrystallized from isopropyl alcohol to give pale yellow powder of (R) -2- [4- {4- [4- (4-chlorophenyl) piperazin-1-yl] piperidine 232 mg (yield 78.1%) of 1-yl} phenoxymethyl] -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole were obtained.
Melting point: 247-249 ° C.

Working Example 3402
(R) -2-Methyl-2- (4- [4- {4- [N-methyl-N- (4-chlorophenyl) amino] piperidin-1-yl} piperidin-1-yl] phenoxymethyl) -6 Preparation of -Nitro-2,3-dihydroimidazo [2,1-b] oxazole (R) -2-Methyl-6-nitro-2- [4- (4-oxopiperidin-1-yl) phenoxymethyl]- 2,3-Dihydroimidazo [2,1-b] oxazole 200 mg in dichloroethane solution (15 ml) 4- [N-methyl-N- (4-chlorophenyl) amino] piperidine 241 mg, sodium triacetoxyborohydride 341 mg and acetic acid 0.092 ml was added and stirred at room temperature for 20 hours. To the reaction mixture was added 20% aqueous sodium carbonate solution, and the mixture was extracted with dichloromethane. The organic layer was dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (dichloromethane: methanol = 20: 1). Recrystallization from a dichloromethane-diethyl ether mixed solvent gave a white powder of (R) -2-methyl-2- (4- [4- {4- [N-methyl-N- (4-chlorophenyl) amino] piperidine- 1-yl} piperidin-1-yl] phenoxymethyl) -6-nitro-2,3-dihydroimidazo [2,1-b] oxazole was obtained in an amount of 105 mg (yield 33.6%).
Melting point: 230.8-232C.

Working Example 3403
(R) -2-Methyl-2- (4- [4- {4- [N-methyl-N- (4-trifluoromethoxyphenyl) amino] piperidin-1-yl} piperidin-1-yl] phenoxymethyl )) Preparation of -6-nitro-2,3-dihydroimidazo [2,1-b] oxazole (R) -2-methyl-6-nitro-2- [4- (4-oxopiperidin-1-yl) phenoxy Methyl] -2,3-dihydroimidazo [2,1-b] oxazole 192 mg in dichloroethane solution (15 ml) 4- [N-methyl-N- (4-trifluoromethoxyphenyl) amino] piperidine 283 mg, triacetoxy hydrogen 328 mg of sodium borohydride and 0.089 ml of acetic acid were added and stirred at room temperature for 14 hours. To the reaction mixture was added 20% aqueous sodium carbonate solution, and the mixture was extracted with dichloromethane. The organic layer was dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (dichloromethane: methanol = 20: 1). Recrystallization from a dichloromethane-diethyl ether mixed solvent gave a yellow powder of (R) -2-methyl-2- (4- [4- {4- [N-methyl-N- (4-trifluoromethoxyphenyl) amino]. 153 mg (yield 47.1%) of piperidin-1-yl} piperidin-1-yl] phenoxymethyl) -6-nitro-2,3-dihydroimidazo [2,1-b] oxazole were obtained.
Melting point: 196-197 ° C.

Example 3404
(R) -2- {4- [4- (4-propylphenylamino) piperidin-1-yl] phenoxymethyl} -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] Preparation of Oxazole (R) -2-Chloro-1- (2-methyl-2-oxiranylmethyl) -4-nitro-1H-imidazole 1.86 g and 4- [4- (4-propylphenylamino) piperidine 1.9 g of 1-yl] phenol was dissolved in 20 ml of DMF, 269 mg of sodium hydride was added, and the mixture was stirred at 50 ° C. for 2 hours. After cooling to room temperature, water and ethyl acetate were added to the reaction solution and the mixture was stirred, and the resulting insoluble matter was collected by filtration. The filtrate was dissolved in dichloromethane, washed with saturated brine and dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane: ethyl acetate = 9: 1 → dichloromethane: methanol = 20: 1). Recrystallization from a mixed solvent of ethyl acetate-diisopropyl ether, pale yellow powdery crystals of (R) -2- {4- [4- (4-propylphenylamino) piperidin-1-yl] phenoxymethyl} -2-methyl- 660 mg (yield 21.9%) of 6-nitro-2,3-dihydroimidazo [2,1-b] oxazole was obtained.
Melting point: 222-223 ° C.

Example 3405
(R) -2- [4- {4- [N-methyl-N- (4-propylphenyl) amino] piperidin-1-yl} phenoxymethyl] -2-methyl-6-nitro-2,3-dihydro Preparation of imidazo [2,1-b] oxazole (R) -2- {4- [4- (4-propylphenylamino) piperidin-1-yl] phenoxymethyl} -2-methyl-6-nitro-2, Dissolve 300 mg of 3-dihydroimidazo [2,1-b] oxazole in a mixed solvent of 4 ml of dichloromethane and 4 ml of methanol, add 0.14 ml of 30% aqueous formaldehyde solution, 115 mg of sodium cyanoborohydride and 0.1 ml of acetic acid, and room temperature Stir overnight. To the reaction mixture was added 20% aqueous sodium carbonate solution, and the mixture was extracted with dichloromethane. The organic layer was dried over magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (dichloromethane: methanol = 40: 1). Recrystallization from a mixed solvent of ethyl acetate-diisopropyl ether yields a slightly yellow powder of (R) -2- [4- {4- [N-methyl-N- (4-propylphenyl) amino] piperidin-1-yl}. 258 mg (83.6% yield) of phenoxymethyl] -2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b] oxazole were obtained.
Melting point: 198-199 ° C.

  The following compounds were prepared as described above.

Example 3505
(R) -6-Nitro-2- {4- [4- (4-trifluoromethylphenoxy) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole melting point: 162-163 ° C.

Test Example 1
Antibacterial test (agar plate dilution method)
With respect to the 2,3-dihydro-6-nitroimidazo [2,1-b] oxazole compound obtained in Example 397, the minimum growth inhibitory concentration to M. tuberculosis (M. tuberculosis H37Rv) was determined by using 7H11 medium (BBL company) ) Was used. The above-mentioned strain is cultured in advance in 7H9 medium (manufactured by BBL), the number of viable cells is calculated, and the final viable cell count is adjusted to about 10 ⁶ CFU / ml using the bacterial solution stored frozen at -80 ° C I kept it. The bacterial suspension thus prepared was inoculated in 5 μl on a 7H11 agar medium containing a test compound and cultured at 37 ° C. for 14 days, and then subjected to a test for measuring the minimum growth inhibitory concentration.

  The minimum growth inhibitory concentration for M. tuberculosis H37Rv was 0.024 μg / ml.

Test example 2
Antibacterial test (agar plate dilution method)
With respect to the 2,3-dihydro-6-nitroimidazo [2,1-b] oxazole compound obtained in Example 2019, the minimum growth inhibitory concentration against Mycobacterium tuberculosis (M. tuberculosis H37Rv) was measured using 7H11 medium (BBL company) ) Was used. The above-mentioned strain is cultured in advance in 7H9 medium (manufactured by BBL), the number of viable cells is calculated, and the final viable cell count is adjusted to about 10 6 CFU / ml using the bacterial solution stored frozen at -80 ° C. It was. The bacterial suspension thus prepared was inoculated in 5 μl on a 7H11 agar medium containing a test compound and cultured at 37 ° C. for 14 days, and then subjected to a test for measuring the minimum growth inhibitory concentration.

  The minimum growth inhibitory concentration for M. tuberculosis H37Rv was 0.0015 μg / ml.

Test Example 3
Antibacterial test (agar plate dilution method)
With respect to the test compounds shown in the following table, the minimum growth inhibitory concentration against M. tuberculosis (K. tuberculosis) was determined using 7H11 medium (manufactured by BBL). The above-mentioned strain is cultured in advance in 7H9 medium (manufactured by BBL), the number of viable cells is calculated, and the final viable cell count is adjusted to about 10 6 CFU / ml using the bacterial solution stored frozen at -80 ° C. It was. The bacterial suspension thus prepared was inoculated in 5 μl on a 7H11 agar medium containing a test compound and cultured at 37 ° C. for 14 days, and then subjected to a test for measuring the minimum growth inhibitory concentration.

  The results are shown in the following table.

Claims (1)

2, 3-dihydro-6-nitro-imidazo [2,1-b] oxazole compound, a pharmaceutical containing at least one selected from the group consisting of optically active forms and pharmaceutically acceptable salts thereof pharmacologically A composition ,
The 2,3-dihydro-6-nitroimidazo [2,1-b] oxazole compound is
(1) 2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethoxyphenoxy) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] Oxazole,
(2) (S) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethoxyphenoxy) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,2, 1-b] oxazole,
(3) (R) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethoxyphenoxy) piperidin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,2, 1-b] oxazole,
(4) 6-nitro-2- {4- [4- (4-trifluoromethoxyphenoxy) piperidin-1-yl] phenoxymethyl} -2,3-dihydro-imidazo [2,1-b] oxazole;
(5) (R) -6-nitro-2- {4- [4- (4-trifluoromethoxyphenoxy) piperidin-1-yl] phenoxymethyl} -2,3-dihydro-imidazo [2,1-b] ] Oxazole,
(6) (R) -2-Methyl-6-nitro-2- {4- [3- (4-trifluoromethoxyphenoxy) -8-azabicyclo [3.2.1] octan-8-yl] phenoxymethyl } -2,3-Dihydroimidazo [2,1-b] oxazole 4-toluenesulfonate,
(7) 2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethylbenzyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] Oxazole,
(8) (R) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethylbenzyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,2, 1-b] oxazole,
(9) 2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethoxybenzyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] Oxazole,
(10) (R) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethoxybenzyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,2, 1-b] oxazole,
(11) 2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethylphenyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] Oxazole,
(12) (R) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethylphenyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,2, 1-b] oxazole,
(13) 2-Methyl-6-nitro-2- {4- [4- (4-chlorobenzyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b] oxazole;
(14) (R) -2-Methyl-6-nitro-2- {4- [4- (4-chlorobenzyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-] b] oxazole,
(15) (R) -2-Methyl-6-nitro-2- {4- [4- (4-chlorophenyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1-b ] Oxazole,
(16) 2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethoxybenzyloxycarbonyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [2,1- b] oxazole,
(17) (R) -2-Methyl-6-nitro-2- {4- [4- (4-trifluoromethoxybenzyloxycarbonyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [ 2,1-b] oxazole and
(18) (R) -2-Methyl-6-nitro-2- {4- [4- (3,4-dichlorobenzyloxycarbonyl) piperazin-1-yl] phenoxymethyl} -2,3-dihydroimidazo [ 2,1-b] oxazole
A pharmaceutical composition which is at least one selected from the group consisting of