TWI314041B - Quinolyl-3-carboxamide compound - Google Patents

Description

MODIFICATION PAGE 1314041 发明 发明 发明 发明 发明 发明 发明 • • • • • • • • • • • • • • • • 喹 喹 喹 喹 喹 喹 喹 喹 喹 喹 喹 喹 喹 喹 喹 喹 喹[Prior Art] In the pamphlet of International Publication No. 073283, N-cycloalkylquinoline carboxamide is described as a therapeutic drug for central nervous system diseases, and is also disclosed in International Publication No. 00/068202. It is described that N-cycloalkyl-4-oxoquinoline-3-carboxamide is a ligand of a GABA acceptor. The cycloalkylamine containing a substituent at the first position is bonded to a 3-quinolinecarboxylic acid. Compound. Further, there is no description of the fungicide for agriculture and gardening. Therefore, the use of the "quinoline-3" carboxamide compound as a fungicide for agricultural and horticultural is not a well-known technique. As a result of intensively repeating the study of the quinoline-3-carboxamide compound, the present inventors have found that a cycloalkylamine or a bonded cycloalkenamine having a substituent on the 3-position is present on the 3-quinolinecarboxylic acid. A quinoline-3-carboxamide compound or a quinoline-3-hydroxy sulfonamide compound is useful as an active ingredient for various plant diseases having excellent bactericidal activity, particularly plant mildew, especially in the case of The present invention has been completed by the agricultural and horticultural use of Pyhcularia oryzae, which provides severe damage, and the gray mold (Botrytis cinerea) for tomatoes, cucumbers and kidney beans, which can be prevented by a low dose. SUMMARY OF THE INVENTION The present invention is as shown in the general formula (1): Revision page 1314041

In the formula, the A system is represented by a C3~Ci ring-ring base which may be substituted by 1 to 4 yards which are the same or different, or a Ci-Cw alkenyl group which may be substituted by the same or different 1~4 yards, R system It is represented by a Cl~c6 alkyl group which may be selected from a halogen atom, 1 to 3 substituents which are the same or different in the group of ^^(^ alkoxy and phenoxy groups, and may be selected from a halogen atom, Ci Substituted with 1 or 3 substituents of the same or different groups of -Ce alkoxy, phenyl and phenoxy groups (: 2~<:6 alkenyl group, which may be selected from a halogen atom, an alkoxy group and a benzene group) The C2 to C6 alkynyl group substituted by the same or different substituents in the group of oxy groups may be selected from the group consisting of a halogen atom, an alkyl group which may be substituted with 1 to 3 halogen atoms which may be the same or different, and a CrCe alkoxy group. The same or different 1 to 2 alkyl-substituted amino groups, nitro, cyano, hydroxy, thiol and CrCe alkylthio groups of the same or different 1 to 6 substituent-substituted aralkyl groups, Or may be selected from the group consisting of a halogen atom, a Ci-Q alkyl group, a «^~decyloxy group, and a hydroxyl group of the same or different substituents of 1 to 6 substituents. The group X is represented by an oxygen atom or a sulfur atom, and the Y system is represented by an alkyl group which may be selected from a halogen atom, which may be substituted with 1 to 3 halogen atoms which may be the same or different, and may have the same or different 1 to 3 halogen atoms. Substituted Ci-Ce alkoxy, phenyl, phenoxy, CrCT decyloxy, amine, nitro, hydroxy, thiol and alkane which may be substituted by the same or different 1-2 Ci-Ce alkyl groups The substituent in the group of the thio group, n is an integer of 0 to 5, and the compound represented by the page 1314041 or a salt thereof is modified. % > ^ The best mode for carrying out the invention - "C3 to Cio ring" in the present invention The alkyl group is, for example, a cyclopentyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group or a norbornene group having a carbon number of 3 to 1 unit, a monocyclic or heterocyclic cycloalkyl group, preferably a cyclopentane group. a group, a cyclohexyl group or a cycloheptyl group, more preferably a cyclohexyl group, "a C3 to C10 cycloalkyl group which may be substituted with 1 to 4 CrCe alkyl groups which are the same or different"", except for the above-mentioned "C3~C1Q cycloalkyl group" , for example: 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,2-dimethylcyclohexyl, 2,6-dimethylcyclohexyl 1 to 4 of the same or different alkyl groups, preferably the above-mentioned "C3~C1G cycloalkyl group" substituted with a methyl group. The "C3~C1Q cycloalkyl group which may be substituted" represented by the A system is preferably The cyclopentyl group, the cyclohexyl group or the cycloheptyl group is more preferably a cyclohexyl group. The "C3~Clc cycloalkenyl group" in the present invention is, for example, a cyclopentenyl group or a cyclohexenyl group having a carbon number of 3 to 10 Monocyclic or heterocyclic cycloalkenyl groups, preferably cyclohexenyl groups. "C3~C1Q cycloalkenyl groups which may be substituted by the same or different 1-4 CrQ alkyl groups", except for the above "C3~C1Q ring" In addition to the alkenyl group, for example, 2-methylcyclohexenyl, 3-methylcyclohexenyl, 4-methylcyclohexenyl, 2,2-dimethylcyclohexenyl, The above-mentioned "C3~C1Q cycloalkenyl group" which is the same or different from 2,6-dimethylcyclohexenyl group. The "C3~C1G cycloalkenyl group which may be substituted" represented by A is preferably a cyclohexenyl group. The "Ci-Ce alkyl group" in the present invention is, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a second butyl group, a tert-butyl group, a pentyl group, Isoamyl, 2-methylbutyl, neopentyl, 1-ethylpropyl, hexyl, 4-methyl 1314041 pentyl, 3-methylpentyl, 2-methylpentyl, 1-methyl Pentyl, 3,3-dimethylbutyl, 2,2-dimethylbutyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethyl a straight or branched alkyl group having 1 to 6 carbon atoms of butyl, 2,3-dimethylbutyl or 2-ethylbutyl group, preferably 1 to 5 straight or branched carbon atoms An alkyl group (C^cs alkyl group), more preferably a carbon number of 1 to 4 linear or branched alkylalkyl groups), still more preferably a carbon number of 1 to 3 straight or branched chains The alkyl group (Ci~C3) is particularly preferably a methyl group, an ethyl group or a propyl group * most preferably a methyl group or an ethyl group. In the present invention, the "c2-c6 alkenyl group" is linear or branched and contains any double bond. For example: vinyl, prop-1-en-1-yl, allyl, isopropenyl, butyl-I-fluorenyl, butyl-2-iso-1-yl, butyl-3-pyrene-1 -yl, 2-methylprop-2-en-1-yl, 1-methylprop-2-en-buyl, pent-1-en-1-yl, pent-2-indol-1-yl, Ethyl-3-phenyl-1-yl, pent-4-ylidene-1-yl, 3-methylbut-2-di-p-yl, 3-methylbut-3-en-1-yl, hex-1 - ene-buyl'hex-2-ene-buyl, hex-3-en-1-yl, hex-4-en-1-yl, hex-5-en-1-yl, 4-methylpentyl 3-ene-1 -yl%=. In the present invention, the "c2 to c6 alkynyl group" is a linear or branched chain and contains any three bonds of φ. For example: ethynyl, prop-1-yn-1-yl, prop-2-yne-buyl, but-1-yn-1-yl, butyl-3-yn-1-yl, 1-methylpropane -2 - alkyn-1-yl, pent-1-yn-1-yl, pent-4-yn-1-yl, hex-1-yn-1-yl, hex-5-yn-1-yl and the like. The "aralkyl group" in the present invention is exemplified by a group in which one or two or more hydrogen atoms of the above ((6-alkyl group) are substituted with an "aryl group". For example: benzyl group ,]-naphthylmethyl, 2-naphthylmethyl, fluorenylmethyl, phenanthromethyl, decenemethyl, diphenylmethyl, 1-phenylethyl, 2-phenylethyl, 1-(1-naphthalene Ethyl, 1-(2-naphthalene)ethyl, 2-(b-naphthalene)ethyl, 2-(2-naphthalene)ethyl, 3-phenylpropyl, 3-(1-naphthalene)propane 1314041, 3-(2-naphthyl)propyl ' 4-phenylbutyl ' 4-(naphthalene)butyl ' 4-(2-naphthyl)butyl, 5-phenylpentyl ' 5-U-naphthalene)pentyl, 5-(2-Naphthalene)pentyl, 6-phenylhexyl, 6-(1-naphthalene)hexyl, 6-(2-naphthalene)hexyl, etc. The "heteroaralkyl" group in the present invention is exemplified by the above a group in which one or two or more hydrogen atoms of "Cl~c6 alkyl group" are substituted with a "heteroaryl group". The heteroaryl group constituting the heteroarylalkyl group is monocyclic or polycyclic, The heteroaryl group of the hetero atom formed by two or more identical or different rings. The type of the hetero atom is not particularly limited, and examples thereof include a nitrogen atom, an oxygen atom, a sulfur atom, and the like. A monocyclic heteroaryl group of an alkyl group, for example, a sulfonyl group, a thienyl group, a pyrrolyl group, a fluorenyl group, an isoxazolyl group, a dihydroisoindole, a thiazolyl 'isothiazolyl group' a 5- to 7-membered monocyclic heteroaryl group such as imidazolyl, pyrazolyl, oxadiazolyl, thiadiazol, triazolyl, tetrazolyl, pyridine, azepine or carbazolevinyl. The polycyclic heteroaryl group of the heteroarylalkyl group is exemplified by a benzofuranyl group, an isobenzofuranyl group, a benzothienyl group, a fluorenyl group, an iso-n-decyl group, a carbazolyl group, a benzoxazolyl group, and a benzene group. Isoxazolyl, benzoxazolyl, benzisothiazolyl, benzoxadiazolyl, benzothiadiazolyl, benzotriazolyl, sialolinyl, isoquinolinyl, porphyrinyl , quinazolinyl, quinoxalinyl, fluorenyl, cyanofluorenyl, fluorenyl, acridinyl, oxazolyl, porphyrinyl, acridinyl, 2 _D丫 steep, 3-anthracene 8 to 14 member polycyclic heteroaryl groups of 4 - acridine, 9 - acridine, porphyrin, thiophene, and morphyl. The "alkoxy" in the present invention is exemplified. For example: methoxy, ethoxy, propoxy, isopropoxy, Oxyl, isobutoxy, second butoxy, tert-butoxy 'pentyloxy, isopentyloxy, 2-methylbutoxy, neopentyloxy, 1-ethylpropoxy, Hexyloxy, (4-methylpentyl)oxy, methylpentyloxy, (2-methylpentyl)oxy, (i-methylpentyl)oxy, 3 3_di-10- 1314041 ^ ^ Amendment page methylbutoxy, 2,2-dimethylbutoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethyl Butoxy, 2,3-dimethylbutoxy '2-ethylbutoxy group having 1 to 6 linear or branched alkoxy groups, preferably having 1 to 4 carbon atoms Or a branched alkoxy group (CrC alkoxy group), more preferably a methoxy group, an ethoxy group or an isopropoxy group, still more preferably a methoxy group or an ethoxy group, most preferably A Oxygen. In the present invention, "(^~(:7醯oxy)" is exemplified by, for example, a methyloxy group, a carbon methoxy group (c2~c7 alkyloxy group) bonded via the above-mentioned "CrCU alkyl group". a carbon methoxy group (c3~c7 olefinic oxy group) bonded via the above "c2~c6 alkenyl group" or a carbon methoxy group bonded via the above "C^Cs alkoxy group" ( C2 to C7 alkoxy group), preferably a linear or branched alkoxy group having 2 to 5 carbon atoms. 0 ((: 2 to 0:5 alkoxy), 2 to 5 carbon atoms A linear or branched alkoxy group ((2:(5) alkoxy), more preferably an ethoxycarbonyl group or a methoxycarbenyloxy group. "Halogen atom" in the present invention The fluorine atom, the chlorine atom, the bromine atom or the iodine atom is preferably a fluorine atom, a chlorine atom or a bromine atom, more preferably a fluorine atom or a chlorine atom, and most preferably a fluorine atom. In the present invention, "Ci" -Ce alkylthio", for example: methylthio, ethylthio, propylthio, isopropylthio, butylthio, isopentylthio, neopentylthio, 3,3. dimethylbutylthio a 2-ethylbutylthio group having 1 to 6 linear or branched alkyl groups, a sulfur group, preferably a carbon number 1 to 4 linear or branched alkylthio groups, more preferably methylthio groups. In the present invention, "C 1 to C 6 alkyl groups which may be substituted by the same or different 1 to 3 halogen atoms", In addition to the above-mentioned "C!~C6 alkyl group", for example: trifluoromethyl, trichloromethyl, difluoromethyl, dichloromethyl, dibromomethyl, fluoromethyl, chloromethyl , bromomethyl, iodomethyl, 2,2,2-trichloroethyl, 2,2,2- -11 - 1314041 Amendment Page 1 Han 4 , σ Trifluoroethyl, 2-Bromoethyl, 〇- Chloroethyl, 2-fluoroethyl, 3-chloropropyl, 3,3,3-trifluoropropyl, 4-fluorobutyl, 3-fluoro-2-methylpropyl, 3,3,3- The above-mentioned "Ci~C6 alkyl group" substituted with the same or different 1-3 "halogen atoms" of the trifluoro-2-methylpropyl group, the 6,6,6-trichlorohexyl group is preferably The above-mentioned "alkyl group" substituted by the same or different 1 to 3 "halogen atoms" described above is more preferably replaced by the same or different "fluorine atom or chlorine atom" as the above-mentioned "Ci~C3 yard base". ' Further more preferably methyl, ethyl, propyl, chloromethyl or trifluoromethyl' is particularly preferably methyl, ethyl or trifluoro In the present invention, the "C^Ce alkoxy group which may be substituted with 1 or 3 halogen atoms which may be the same or different" is, for example, a trifluoromethoxy group other than the above-mentioned "CrCe methoxy group". , trichloromethoxy, difluoromethoxy, dichloromethoxy, dibromomethoxy, fluoromethoxy, chloromethoxy, bromomethoxy, iodomethoxy '', 2, 2,2-trichloroethoxy, 2,2,2-trifluoroethoxy, 2-bromoethoxy, 2-chloroethoxy, 2-fluoroethoxy, 3-chloropropoxy, 3,3,3-trifluoropropoxy, 4-fluorobutyl, 3-fluoro-2-methylpropoxy, 3,3,3-trifluoro-2-methylpropoxy, 6,6 The above-mentioned "alkoxy group" substituted with 1 or 3 of the above-mentioned "halogen atoms" of the same or different hexachlorohexyloxy group is preferably the same or different 1 to 3 of the above-mentioned "halogen atom". The above-mentioned "C1 to C4 alkoxy group" is more preferably substituted with the above-mentioned "C^C3 alkoxy group" which may be substituted by the same or different 1 to 3 "fluorine atoms or chlorine atoms", and furthermore Preferred is methoxy, ethoxy, propoxy or trifluoromethoxy, most preferably methoxy. In the present invention, "a Cl~C6 alkyl group which may be selected from the group consisting of a halogen atom, a group of 1 to 3 substituents which are the same or different in the group of alkoxy groups and phenoxy groups", in addition to the above" The alkyl group and the above-mentioned "Cl~c6 alkyl group which may be substituted by 1 or 3 halogen atoms which may be the same or different" include methoxy-12-, · t ·· ····::--. ' ί ' 一 — l. * . - Amendment 1; Π14041 methyl, ethoxymethyl, ethoxyethyl, propyl, etc., the same or different 1~3 of the above-mentioned "CrC6 alkoxy" substitution The above-mentioned "Cl~c6^ group", the above-mentioned "CrC6 alkyl group" substituted with a phenoxy group such as a phenoxymethyl group or a phenoxyethyl group, and 2-methoxy-1-chloromethyl group The above-mentioned one of two or more substituents selected from the group consisting of a halogen atom, the above alkoxy group, and a phenoxy group, and a 3-phenoxy-2-bromo-2-methoxypropyl group "Cl~C6^基". In the present invention, "may be substituted with one or three substituents which are the same or different in the halogen atom, the group of (^ alkoxy, phenyl and phenoxy groups). C2~C6 storage base", except for the above "C In addition to the 2~C6 susceptibility, the above-mentioned "C2~C6" which is substituted with the same or different 1~3 halogen 0 atoms such as 3-chloroallyl group and 4-bromo-2-butenyl group is also included. "Alkenyl", substituted by the same or different 1 to 3 of the above "alkoxy" groups such as 3-methyl-alkyl-2-propenyl or 4-ethoxy-3-butenyl, and the above-mentioned "C2~ C6 alkenyl", the above-mentioned "C2~C6 alkenyl group" substituted with a phenyl group such as a 1-styryl group, a styryl group or a cinnamyl group, and a phenoxy group such as a 3-phenoxy-2-butenyl group Two or more of the above-mentioned "c2 to C6 alkenyl group" and 4-methoxy-3_chloro-2-butenyl group, a halogen atom, the above-mentioned Ci-Ce alkoxy group, and a phenoxy group The above-mentioned "(:2~(:6 alkenyl)" which is substituted by a substituent. In the present invention, "the substituent which may be selected from the same or different U substituents in the group of a halogen atom, an alkoxy group and a phenoxy group may be substituted. The (:2-06 alkynyl group)' includes, in addition to the above-mentioned "C2 to C6 alkynyl group", selected from the group consisting of 3·chloro-2-propynyl group, 4-bromo-2-butynyl group, and the like. The above-mentioned "C2 to C6 alkynyl group" is substituted by the same or different 1 to 3 halogen atoms, and 3-methoxy- The above-mentioned "C2 to C6 alkynyl group" substituted by the same or different "Cl~C: 6-homoyloxy group" such as 2-propynyl group and 4-ethoxy-3-butynyl group, 3-phenoxy-2-butynyl and the like -13- 1314041 ★ P modified page phenoxy substituted above "C2~c6 alkynyl", and 4-methoxy-4-chloro-2-butyl The above-mentioned "C2 to C6 alkynyl group" in which two or more substituents in the group of the alkynyl group, the halogen atom, the alkoxy group, and the phenoxy group are substituted. In the present invention, "an amine group which may be substituted with 1 or 2 Ci~Cs groups which are the same or different" is substituted with the same or different 1~2 of the above alkyl groups except for the amine group. The amine group is preferably an amine group which may be the same or different 1 to 2 of the above-mentioned "alkyl group", and more preferably a dimethylamino group or a diethylamine. In the present invention, "Ci-Ce alkyl group, alkoxy group which may be substituted by a halogen atom, which may be the same or different from 1 to 3 halogen atoms, may be the same or different 1 to 2 (^~( ^Alkyl-substituted amine, nitro, cyano, hydroxy, thiol and thio group of the same or different 1 to 6 substituents substituted aralkyl"" in addition to the above "aralkyl" In addition, the above-mentioned "aralkyl group" substituted with the same or different 1 to 6 halogen atoms, the same or different 1 to 6 of the above-mentioned "the same or different i~3 halogen atoms may be substituted for C. "C6 alkyl" is substituted with the above-mentioned "aralkyl group", and the same or different 1 to 6 of the above-mentioned "(^-(alkoxy)" substituted "aralkyl group", the same or different 1 to 6 of the above-mentioned "aralkyl groups which may be the same or different 1 to 2 (: 1 to 6 alkyl substituted amino group), and 1 to 6 nitro groups substituted by the above" "aralkyl group", 1 to 6 cyano groups substituted with the above "aralkyl group", 1 to 6 interesting groups substituted with the above "aralkyl group", 1 to 6 hydrogenthio group substituted In addition to the above-mentioned "aralkyl group" which is substituted by the same or different 1 to 6 "Cl~C6 alkylthio groups", the halogen atom and the above "may be the same or different" 1 to 3 halogen atoms substituted by Cl~c6 alkyl", the above-mentioned "CrC6 hospitaloxy", the above "may be the same or different ^ Ci~c6 -14-1314041 modified page spleen:, ην9 hospital The above-mentioned "aryl-fluorenyl group" substituted with two or more substituents in the group of the "Cl~C6 alkylthio group" in which the amino group is substituted with an amino group, a nitro group, a cyano group or a hydroxyl group. When the aralkyl group has a substituent, the substituent is substituted on either or both of the aryl ring constituting the aralkyl group or the alkyl group. In the present invention, "a halogen atom, Cl~c6 may be used. a heteroarylalkyl group substituted with the same or different 1 to 6 substituents in the group consisting of an alkyl group, a CrCe alkoxy group and a hydroxyl group, is the same or different except for the above-mentioned "heteroarylalkyl group". The above-mentioned "heteroaralkyl group" substituted with 1 to 6 halogen atoms is substituted with the same or different 1 to 6 of the above-mentioned "Cl~C6 alkyl group" The above-mentioned "heteroaralkyl group" is substituted with the above-mentioned "an aralkyl group" substituted with the same or different 1 to 6 of the above alkoxy groups, and the above-mentioned "heteroaralkyl group substituted with 1 to 6 hydroxyl groups" "Other than" includes the above-mentioned "heteroarylalkyl group" substituted with two or more substituents selected from the group consisting of a halogen atom, the above-mentioned "alkyl group", the above-mentioned "alkoxy group", and a group of a hydroxyl group. In the case where the aralkyl group has a substituent, the substituent is substituted on either or both of the heteroaryl ring constituting the heteroarylalkyl group. The Y system may be substituted on the quinoline ring. When 1 to 5 are substituted at any position of the substitution, and Y is present in two or more, they may be the same or different. The compound (1) of the present invention is: (1) A is preferred. It is a C3~C1Q cycloalkyl group which may be substituted with 1 to 4 methyl groups, more preferably a cyclopentyl group, a cyclohexyl group or a cycloheptyl group, particularly preferably a cyclohexyl group, and (2) the R system may be the same or different. 1 to 6 halogen atoms, Ci~C6 alkyl groups, alkoxy groups or hydroxy-substituted aralkyl groups, more preferably 1 to 6 halogen atoms which may be the same or different, Cr Ce alkyl, alkoxy or hydroxy-substituted benzyl is particularly preferably benzyl '(3)X is preferably an oxygen atom, -15- 1314041 0, r is modified (4) Yn is preferably Y is a fluorine atom, a hydroxyl group or a methyl group, ! is 0 or 1, more preferably Υ is methyl and η is 0 or 1. With respect to the compound (1) of the present invention, it is preferred that the (al) A system is a c3 to C1() cycloalkyl group which may be substituted with 1 to 4 methyl groups, and the (a2) R system may be the same or different from 1 to 6 a halogen atom, (^~(:6 alkyl, 〇^~(:6 alkoxy or hydroxy-substituted aralkyl, (a3) X is an oxygen atom, (a4) Yn is Y is a fluorine atom, a hydroxyl group or a methyl group, n is ruthenium or 1, more preferably (bl) is a cyclopentyl group, a cyclohexyl group or a cycloheptyl group, and (b2) R is a group of 1 to 6 halogen atoms which may be the same or different, a CrCe alkyl group, an alkoxy group or a hydroxy group-substituted benzyl group, (b3) X is an oxygen atom, (b4) Y is a methyl group, η is 0 or 1, and more preferably (cl) A is a ring. The hexyl group, (c2) R is a benzyl group, (c 3 ) X is an oxygen atom, (c4) Yn wherein Y is a methyl group, η is 0 or 1, most preferably (d) a compound (1) It is: N-(l-benzylcyclohexyl)quinoline-3-carboxamide, N-(l-benzylcyclohexyl)quinoline-3-hydroxythioantamine, N-[l-(3 -fluorobenzyl)cyclohexyl]quinoline-3-carboxamide, N-[l-(4-fluorobenzyl)cyclohexyl]quinoline-3-carboxamide, N-(l-benzene Cyclohexyl)-8-methylsalazine-3-residic acid amine, N-1-benzyl group Hexyl) -8 - quinoline-3-fluoro-2carboxamide, N- (l- benzyl-methylcyclohexyl) -8-fluoro-3-hydroxyphenyl sulfur Amides' -16--1314041

Amendment page N-(l-N-methylcyclohepta)quinoline-3-amine, ν·[1-(3,4·difluorobenzyl)cyclohexyl]quinoline-3-carboxamide, Or N-[l-(3,5-difluorobenzyl)cyclohexyl]quinoline-3-carboxamide. The compound (1) of the present invention is, for example, a salt of a sulfate, a hydrochloride, a nitrate or a phosphate. These salts are limited to use as agricultural and horticultural fungicides, and are included in the present invention. When the compound (1) of the present invention and salts thereof are solvents and substances, such solvents and substances are also included in the present invention. The solvent and the substance are preferably water and substances.

In the case where the compound (1) of the present invention contains a compound of an asymmetric carbon, the present invention also includes a mixture of an optically active substance and a plurality of optically active substances in an arbitrary ratio. Representative compounds of the present invention are shown, for example, in the following tables, but the compounds of the present invention are not limited thereto.

The following are the various abbreviations in the present invention, "cPen" is a cyclopentyl group, "cHeX" is a cyclohexyl group, "cHep" is a cycloheptyl group, and "Nor" is an original norbornene group, " cHeXe" is cyclohexenyl, "Me" is methyl, "Et" is ethyl, "P" is propyl, "iPr" is isopropyl, "Bu" is butyl, "iBu" is isobutyl, "Ph" is phenyl, "Allyl" is allyl, "Propar" is propargyl, "Bn" is benzyl, and "Phene" is benzene. Ethyl, "Sty" is a styryl group, "Cin_ is a cinnamyl group, "ISOXM" is an isoxazole methyl group, "ISTAM" is an isothiazolylmethyl group, and "PYRM" is a pyrazole methyl group. "THIM" is thiazolylmethyl, "ISDM" is 4,5-dihydroisoxazole methyl, "BZTM" is benzothiazolylmethyl, "NAPM" is naphthylmethyl, "PYDM" It is a pyridylmethyl group, and "Η" in "Yn" is n = 0. -17- 1314041

Compound number ARX Yn 1-1 cHex Me 0 H 1-2 cHex Et 0 H 1 -3 cHex Pr 0 H 1"4, cHex Bu 0 H 1-5 cHex iBu 0 H 1-6 cHex 2-Et-Bu 0 H 1-7 cHex MeOCHz 0 H 1-8 cHex PhOCH2 0 H 1-9 cHex Ally! 0 H 1-10 cHex Propar 0 H 1-11 cHex Bn 0 H 1-12 cHex 2-Me ~Bn 0 H 1- 13 cHex - Bn 0 H 1-14 cHex 4—Me—Bn 0 H 1-15 cHex 2-GI-Bn 0 H 1-16 cHqx 3-C Bu Bn 0 H Bu 17 cHex 4-G Bud π 0 H 1-18 cHex 2-F-Bn 0 H 卜 19 cHex 3- 0 H 1-20 cHex 4-F-Bn 0 H 1 - 21 cHex Phene 0 H 1-22 cHex Sty 0 H 1-23 cHex Cin 0 H 1-24 cHex 1SOXM 0 H . 1-25 cHex ISTAM 〇H 1-26 cHex PYRM 〇H 1-27 cHex Bn .〇2-Me

-18- 1314041

1-28 cHex Bn 0 4-Me 1-29 cHex Bn 〇5—Me 1-30 cHex Bn 0 6-Me 1-31 cHex Bn 0 7-Me 1-32 cHex Bn .0 8-Me 1-33 cHex Bn 0 2 - Et 1-34 cHex Bn 0 4-Et 1-35 cHex Bn 0 5-Et 1-36 cHex Bn 〇6-Et 1 - 37 cHex Bn 0 7-Et 1-38 cHex Bn 0 8-Et 1-39 cHex Bn 0 8-Pr 1-40 cHex Bn 0 8-iPr 1-41 cHex Bn 0 5-F 1-42 ' cHex Bn 0 6-F 1-43 cHex Bn 0 7-F 1-44 cHex Bn 0 8-F 1-45 cHex Bn 0 5—MeO 1-46 cHex Bn 0 6—MeO 1-47 cHex Bn 0 7-MeO 1-48 cHex Bn 0 8-MeO 1-49 cHex Bn 0 8-EtO 1-50 cHex Bn 0 8-MeS 1-51 cHex 巳n 0 8-OH 1-52 cHex Bn s H 1-53 cHex 2—Me~Bn s H 1-54 cHex 3-Me-Bn s H 1- 55 cHex 4-Me_Bn s H 1-56 cHex 2-Cb Bn s H 1-57 cHex 3~Cl"Bn s H 1-58 cHex 4-CI-Bn s H 1-59 cHex 2-F-day ns H 1-60 cHex 3-F-Bn s H 1-81 cHex 4—p—Bn s H 1-62 cHex Bn s 2-Me 1-63 cHex Bn s 4-Me 1TM64 cHex 巳r> s 5 —Me 1-65 cHex Bn s 6 - Me 1-66 cHex Bn s 7—Me 1-67 cHex Bn s 8-Me 1-68 cHex Bn s 5-F 1-69 cHex Bn s 6-F

-19- 1314041

1-70 cHex Bn S 7-F 1-71 cHex Bn S 8-F 1-72 cHex Bn s 8-OH 1-73 cPen Bn 0 H 1-74 cHep Bn 0 H 1 - 75 Nor Bn 0 H 1- 76 2-Me-cHex Bn 0 H 1-77 3~Me—cHex Bn 0 H 1-78 4—Me - cHex Bn 0 H 1-79 cHexe Bn 0 H 1-80 cPen Bn 0 2-Me 1 - 81 cPen Bn 0 4-Me 1-82 cPe threshold 0 0 0~Me 1-83 cPen Bn 0 6-Me 1-84 ' cPen Bn 0 7-Me 1-85 cPen Bn 0 8-Me 1-86 cPen Bn 0 5-F 1-87 cPen Bn 0 6-F 1-88 cPen ' Bn 0 7-F 1-89 cPen Bn 0 8-F 1-90 cPen Bn 0 8-OH 1-91 cPen 2- Me—Bn 0 H 1-92 cPen 3-Me-Bn 0 H 1-93 cPen 4~Me—Bn 0 H 1-94 cPen 2-CI-Bn 0 H 1-95 cPen 3-ChBn 0 H 1-96 cPen 4- CI-Bn 0 H 1-97 cPen 2-F - Bn 0 H 1-98 cPen 3-F-Bn 0 H 1-99 cPen 4 -F-Bn 0 H 1 ~1〇0 cHep Bn 0 2-Me 1 -101 cHep Bn 0 4-Me 1-102 cHep Bn 0 5—Me 1-103 cHep Bn 0 6-Me 1-104 cHep Bn 0 7—Me 1-105 cHep Bn 0 8-Me 1-106 cHep Bn 0 5-F 1-107 cHep Bn 0 6-F 1-108 cHep Bn 0 7-F 1-109 cHep Bn 0 8-F 1-110 cHep Bn 0 8-OH Bu 111 cHep 2 - Me-Bn 0 H

-20 1314041 1-112 cHep 3—Me—Bn 0 H 1-113 cHep 4 —Me—Bn 〇H 1-114 cHep 2-Cl-Bn 〇H 1-115 .cHep 3-CI-Bn 0 H 1- 116 cHep 4-ChBn 0 H 1-117 cHep 2-F-Bn 0 H 1-118 cHep 3-F-Bn 0 H 1-119 cHep 4-p*Bn 0 H 1-120 cHex Bn 0 5-CF3 1 -121 cHex Bn 0 6 - CF3 1-122 cHex Bn 0 7-CF3 1-123 cHex Bn 0 8-CF3 1-124 cHex Bn 0 8-CF30 1-125 cHex 2-NOz-Bn 0 H 1H26 cHex 4— N02_B n 0 H 1-127 cHex 2—NH “Bn 0 H 1H2B cHex 4-NH “Bn 0 H 1-129 cHex 2-MeNH-Bn 0 H 1-130 cHex 4*MeNH^Bn 0 H 1-131 cHex 2-SH-Bn 0 H 1-132 cHex 4-SH-Bn 0 H 1-133 cHex 2-MeS*Bn 0 H 1-134 cHex 4**MeS-Bn 0 H 1-135 cHex Bn 0 6,7 -F2,8-EtO 1-136 cHex Bn 0 6(7f8-Fa 1-137 cHex 2~*MeO—Bn 0 H 1-138 cHex 3-MeO-Bn 0 H 1-139 cHex 4-MeO-Bn 0 H 1-140 cHex 2—MeO-Bn s H 1-141 cHex 3-Me〇-Bn s H 1-142 cHex 4—MeO_Bn s H 1-143 cHex 2-MeO-Bn 0 4—Me 1-144 cHex 3~M©0~Bn 0 4-Me 1-145 cHex 4—MeO-Bn 0 4-Me 1-146 cHex 2-OH-Bn 0 H 1-147 cHex 3-OH-Bn 0 H 1-148 cHex 4-OH-Bn 0 H 1-149 cHex 2-OH-Bn s H 1-150 cHex 3-OH-Bn s H 1-151 cHex 4~OH_Bn s H 1-152 cHex 2-OH-Bn 0 4—Me 1-153 cHex 3-OH-Bn 0 4~Me 1-154 cHex 4-OH- Bn 〇4-Me 1314041 1-155 cHex 2"Br-*Bn 1-156 cHex 3-巳r-Bn 1-157 cHex 4-Br-Bn 1-158 cHex 2-Br-Bn 1-159 cHex 3- Br-Bn 1-160 cHex 4-Br-Bn 1-161 cHex 2 - Br-Bn 1-162 cHex 3-Br-Bn 1-163 cHex 4-Br-Bn 1-164 cHex 2—CN*-*Bn 1-165 cHex 3-CN-Bn 1-166 cHex 4-CN-巳n 1-167 cHex 2-CN-Bn 1-168 * cHex 3-CN-Bn 1-169 cHex 4-CN-Bn 1-170 cHex 2-CN-Bn 1-171 cHex 3-CN-Bn 1-172 cHex 4-CN-Bn 1-173 cHex 2-CFq-Bn 1-174 cHex 3-CFa-Bn 1-175 cHex 4-CF3- Bn 1-176 cHex 2-CF3-Bn 1-177 cHex 3-CFrBn 1-178 cHex 4-CF3-Bn 1-179 cHex 2-CF3-Bn 1-180 cHex 3-CFrBn 1-181 cHex 4-CF3- Bn 1-182 cHex Ethynyl 1-183 cHex Ethynyl 1-184 cHex Ethynyl 1-185 cHex Ethynyl 1-186 cHex Ethynyl 1-187 cHex Ethynyl 1-188 cHex Ethynyl 1-189 cHex Ethynyl 1-190 cHex Ethynyl 1-191 cBu Bn 1-192 cBu Bn 1-193 cBu Bn 1-194 cPen Bn 1-195 cHep Bn 1-196 2-Me-cHex Bn 1-197 3-Me-cHex Bn 1-198 4-Me - cHex Bn 1-199 cHex 3-F**Bn 1-200 cHex 4-F-Bn 1-201 cHex Bn ooosssoooooosssoooooosssoooooosssoooosossooooos Η Η Η Η Η Η 4"Me 4-Me 4-Me Η Η Η Η Ή Η 4 4-Me 4_Me 4-Me Η Η Η Η Η Η 4-Me 4-Me 4—Me Η Η Η Η Η Η 4 One Me 4—Me 4*~Me Η Η 4 One Me Η Η 4-Me 4-Me 4-Me 4_Me 4-Me

8-MeO -22- 1314041 1-202 cHex 3F, 4Me*~Bn 0 H 1-203 cHex 2Me,3F-Bn 〇H 1-204 cHex 2Mef5F-Bn 0 H 1-205 cHex 3F,4Me—Bn SH 1 -206 cHex 2Me,3F*"Bn SH 1-207 cHex 2Met5F~Bn SH 1-208 cHex 3F,4Me—Bn 0 4-Me 1-209 cHex 2Me,3F-巳n 〇4-Me 1-210 cHex 2Me?5F-Bn 0 211 211 cHex 2,3F2_Bn 〇H 1-212 cHex 2,5F2_Bn 0 H 1-213 cHex 3,4F2-Bn o H 1-214 cHex 3,5F2-Bn 0 H 1-215 cHex 2 ,3F2-Bn s H 1-216 ' cHex 2,5F2-Bn s H 1-217 cHex 3,4F2-Bn s H 1-218 cHex 3,5F2-Bn s H 1-219 cHex 2,3F2-Bn 〇 4 Me 1-220 cHex 2t5FrBn 0 4-Me 1-221 cHex 3,4F2*~Bn 〇4-Me 1-222 cHex 3»5F Plant Bn 0 4-Me 1-223 cHex 2,3CVBn 〇H 1- 224 cHex 2,5CI2-Bn 0 H 1-225 cHex 3,4CI2-Bn 0 H 1-226 cHex 3,5ClrBn 0 H 1-227 cHex 2,3Ci2-Bn s H 1-228 cHex 2,5ClrBn s H 1 -229 cHex 3,4CI2-Bn s H 1-230 cHex 3,5CI2-Bn s H 1-231 cHex 2,3Cl2-Bn 0 4-Me 1-232 cHex 2,5Ci2-Bn 0 4-Me 1-233 cHex 3,4CIZ-Bn 0 4-Me 1-234 cHex 3,5GI2- Bn 0 4~Me 1-235 cHex 3-THIM 0 H 1-236 cHex 3-Me-2-THIM 0 H 1-237 cHex 2 .5Me Plant 3 - THIM 0 H 1-238 cHex 3-Me-ISDM 0 H 1-239 cHex 3-Me-ISOXM 〇H 1-240 cHex 3-BZTM 0 H 1-241 cHex 1-NAPM 0 H 1- 242 cHex 2-NAPM 0 H 1-243 cHex 2-PYDM 0 H 1-244 cHex 3-PYDM 0 H 1-245 cHex 4-PYDM 0 H 1-246 cHex 1-Ph-vinyl 〇H 1-247 cHex 1 One Ph-ethyl 0 H 1-248 cHex 1-Ph-ethyI 〇4-Me

-23- 1314041 % ^ Amendment page The more suitable compounds of the above exemplified compounds are compound numbers 1-1, 1-5, 1-11, 1-12, 1-13, 1-14, 1-15' 1-16' 1-17, 1-18, 1-19, 1-20, 1-28, 1-30, 1-32, 1-44, 1-52' 1-67, 1-71, 1- 73' 1-74' 1-75' 1-77' 1-78' 1-123' 1-135' 1-138' 1-139' 1-146, 1-156, 1-194, 1-195, 1-199, 1-200, 1-208, 1-210' 1-213 ' 1-214, 1-219, 1-220, 1-221, 1-222, 1-235, 1-239, 1- Compounds of 242, 1-244, 1-246, 1-247 or 1-248, more preferably compound numbers 1-1, 1-14, 1-17, 1-19, 1-20, 1-28, 1 -32, 1-44, 1-52' 1-71 ' 1-73, 1-74, 1-77 ' 1-135, 1-139' 1-56, 1-200 ' 1-213, 1-214 Or a compound of No. 1-235, further preferably a compound number 1-1-1, 1-19 '1-20 ' 1-32, 1-44, 1-52 ' 1-71, 1-74 > 1-213 And compounds of No. 1-214. The quinoline-3-carboxycarboxamide compound of the present invention is produced by the methods A and B described below, and the porphyrin-3-hydroxythioguanamine compound is produced by the C method described below.

(Method A) The 'A, R, Υ, and η lines in the above formula have the same meanings as described above. The oxime method is a method in which a carboxylic acid is condensed with an amine to produce the compound (la) (x = 0) of the present invention. (Step A-1) -24- 1314041 Compound (Π) in the step A-1, which is halogenated by a halogenating agent in an inert solvent to produce a halogenated 3-quinoline ruthenium compound represented by the formula (III) The steps. The halogenating agent used in this step is not particularly limited as long as it is an acid halide of a carboxylic acid, and an inorganic halogen compound such as phosphine chloride, thiophosphorus chloride, phosphorus pentachloride or phosphorus trichloride can be obtained; Or an organic halogen compound such as α-(2-dihalogenated ether 'halogenated alkylamine, organic dish halide, or the like, preferably an organic halogen compound, more preferably chlorinated grass. The solvent used in this step is resistant. When reacting/not specifically limiting, for example, hydrocarbons such as hexane, cyclohexane, benzene, and toluene; halogenated hydrocarbons such as dichloromethane, dichloroethane, chloroform, and tetrachloroethane; An ether such as decane, diethyl ether, tetrahydrofuran (THF) or ethylene oxide dimethyl ether; a ketone such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone; a dinitrile or isobutyronitrile; a nitrile; or an ester of methyl acetate, ethyl acetate, propyl acetate or the like, preferably a hydrocarbon or a halogenated hydrocarbon, more preferably benzene, toluene, dichloromethane or dichloroethane. The raw material compound, the reaction reagent, the solvent, and the like are different, and are usually - 20 ° C to 250 ° C, preferably 0t~140° C. φ The reaction time varies depending on the starting compound, the reaction reagent, the solvent, the reaction temperature, etc., and is usually 10 minutes to 120 hours, preferably 30 minutes to 72 hours. The compound (IV) of the oxime-2 step, the step of the compound (Ia) of the present invention is produced by deuteration of the compound (I) in an inert solvent, in the presence or absence of a base. The amount of (III) is usually from 1 to 3 moles, preferably from 1.1 to 1.5 moles, per mole of the compound (IV), -25 to 1314041. In the case where bases are used in this step, The base may be a base user in a usual reaction', and is not particularly limited, for example, an alkali metal carbonate of sodium carbonate or potassium carbonate; an alkali metal hydrogencarbonate of sodium hydrogencarbonate or potassium hydrogencarbonate; Alkali metal hydroxide of sodium hydroxide, lithium hydroxide or potassium hydroxide; alkali metal hydroxide or alkaline earth metal hydroxide of sodium hydroxide, potassium hydroxide or barium hydroxide; sodium methoxide, An alkali metal alkoxide of sodium ethoxylate or potassium third butoxide; Triethylamine, tributylamine, diisopropylethylamine, N-methylmorpholine, pyridine, 4-(N,N-dimethylamine)pyridinium, N,N-dimethylaniline,® N, N-diethylaniline, 1,5-diazabicyclo[4. 3. Ο]indolyl-5-salt, 1,4-diazabicyclo[2. 2. 2]octane (DABCO) , 1,8-diazabicyclo[5. 4. 〇]-7-undecene (DBU) organic bases; or butyl lithium, lithium diisopropyl decyl amines The class is preferably an organic base, more preferably triethylamine or pyridine. The amount of base used is 1 mol relative to the compound (ZV), usually 3 0 mol, preferably 1.1-. 15 moles. The solvent used in this step is not particularly limited when the solvent is used to prevent the reaction, and hydrocarbons such as hexane, cyclohexane, benzene, toluene, etc. can be obtained; dichloroformamidine, monochloroethylene a halogenated hydrocarbon such as alkane, chloroform or tetrachloroethane; an ether such as alkane, diethyl ether, tetrahydrofuran (THF) or ethylene oxide dimethyl ether; dimethylamine, dimethyl Amidoxime, guanamine such as hexamethylene hexamethylphosphate (HMpA); acetone, methyl ethyl ketone 'methyl isobutyl ketone, ring a ketone such as ketone or the like; a nitrile such as propionitrile or isobutyronitrile; or a vinegar of methyl acetate, ethyl acetate or propyl acetate is preferably a halogenated hydrocarbon or ether, more preferably Dichloromethane, dichloroethane or THF. -26- 1314041 The reaction temperature varies depending on the starting compound, the reaction reagent, the solvent, etc., and is usually - 20 ° C to 150 ° C, preferably crc 40 ° C. The reaction time varies depending on the starting compound, the reaction reagent, the solvent, the reaction temperature, etc., and is usually from 10 minutes to 120 hours, preferably from 30 minutes to 72 hours. The 3-quinoline carboxyoxy compound (丨丨) of the starting material of the above-mentioned method A is a conventional compound, or a conventional method 1 is exemplified by, for example, Medical Journal of Chemistry _j. Med Chem., 22 pp. 816 ( Prepared for manufacture according to Method 1 described in 1979). The amine compound (lv) used in this step is a conventional compound or a method known in the art (for example, from Chemical Report Chem. Ber., p. 12, page 1875 (18-9)). A method of hydrating a carboxylic acid by an amine compound obtained by a shift reaction, or a hydrolysis reaction obtained by synthesizing Synthesis, '12, 巻 17〇 9 (2000) by a Ritter reaction of an alcohol compound The amine compound is prepared by the method 1 in which the amine compound is prepared. (Method B)

(V) (la)

In the above formula, the A, R, Υ, and n series have the same meanings as described above. The B method is a method for producing a compound of the present invention by reacting a nitrile with an alcohol. (B-1 step) The compound (V) of the step B-1 is in a solvent or a non-solvent, and is borrowed in the presence of an acid. The amount of the compound (VI) used in the reaction of the compound (vi) to produce the compound of the present invention (u, '-27- 1314041, relative to the compound (v), usually 1 to 6 moles The ear is preferably 1.1 to 3.0 mol. In the case of using the solvent in the present step, the solvent to be used is not particularly limited, and may be, for example, hexane, cyclohexan, octane, or the like. a hydrocarbon; a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride; an ether such as dioxane, diethyl ether, tetrahydrofuran (THF) or dibutyl ether; or a carboxylic acid such as acetic acid or propionic acid. Preferably, it is a carboxylic acid, more preferably acetic acid. The acid used in this step is not particularly limited because it is used in the usual Ritter reaction, and may be, for example, sulfuric acid, formic acid, pity. Acid, inorganic acid of perchloric acid; organic acid of benzenesulfonic acid, toluenesulfonic acid; or tetrachloro The tin-trifluoroborate Lewis acid, preferably a mineral acid, more preferably sulfuric acid. The amount of acid used is usually 1-6 mol relative to the compound (V) 1 mol, preferably The reaction temperature varies depending on the starting compound, the reaction reagent, the solvent, etc., and is usually -20 ° C to 10 ° C, preferably 0. (: -80. (: The reaction time varies depending on the starting compound, the reaction reagent, the solvent, the reaction temperature, etc., and is usually from 15 minutes to 120 hours, preferably from 30 minutes to 72 φ hours. The porphyrin compound (VI) is a conventional compound, or a method described in a conventional method, for example, J. _M e cL C hem., p. 22, p. 816 (1979). 1. Preparation for production. The alcohol compound (V) used in this step is a conventional compound or a method known in the art (for example, tetrahedron Tetrahedron, p. 55, p. 4595 (1999)) And ready to manufacture. (Method C) -28- 1314041

In the above formula, A, R, γ, and n have the same meanings as described above. The c method is a method of producing the compound (lb) (X = S) of the present invention by sulfurization of the compound (Ia) (x = 0) of the present invention. (C-1 step) The compound (I a) of the step c-1 is produced by reacting with a sulfur carbonization agent in a solvent or a non-solvent, in the presence or absence of a base, in the presence or absence of a base. The step of the compound (〗 〖b). The sulphur carbonization agent used in this step is not particularly limited as long as it is used in a usual sulphur carbonization reaction, and may be, for example, phosphorus pentasulfide or Lawson's reagent (2,4-di ( 4-methoxyphenyl)-i,3-dithia-2,4-diphosphonate-2,4-disulfide), bis(dimethylamine)thiophosphoric acid, or diethyldithiophosphoric acid Preferably, phosphorus pentasulfide or Lawson's reagent is used. The sulfur carbonization dose to be used is usually 0.5 to 6 moles, preferably 0.5 to 3.0 moles, relative to the compound (I a ) 1 mole. φ When the solvent is used in this step, and the solvent used is not harmful to the reaction, it is not particularly limited, and may be, for example, a hydrocarbon such as hexane, 'cyclohexane, benzene, toluene or xylene. a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride; or an ether such as dioxane, diethyl ether, tetrahydrofuran (THF) or dibutyl ether, preferably a hydrocarbon, more preferably toluene. . In the case of using the base in the present step, the base used is a base user in a normal reaction, and is not particularly limited, and may be, for example, an alkali metal carbonate of sodium carbonate or potassium carbonate; or hydrogen carbonate. Sodium, potassium hydrogencarbonate alkali gold. -29- 1314041 is a hydrogencarbonate; sodium hydroxide, hydrazine hydrate; sodium hydroxide, potassium hydroxide, nitrogen oxides alkaline earth metal hydroxide; sodium methoxy Oxygen salts of metallurgical institutes; triethylamine methylmorpholine, pyridine, 4-(N,N-diethylaniline, 1,5-diazabicyclo ring [2.2.2] octane (DABCO), alkali metal hydroxide of potassium hydroxide, alkali metal hydroxide or sodium ethoxylate, potassium hair-butoxy salt ' Ξ butylamine, diisopropane ethylamine, N _ methylamine Pyridine, N,N-dimethylaniline, N,N-[4.3.0]non-5-alkane, 1,4-diazadi 1,8-diazabicyclo[5.4.0:1-7 - an organic base or a hexene metal of the decene (DBU), preferably an organic base, and more preferably a pyridine or a lithium diisopropane decylamine. ·

The amount of base which is usually used in the range of 1 to 6 is preferably 1.1 to 3 moles per mole of the compound (a). The reaction temperature varies depending on the starting compound, the reaction reagent, the solvent, etc., and is preferably 〇C~20〇C', preferably 2〇°c~is〇°c. The reaction time varies depending on the starting compound, the reaction reagent 'solvent and the reaction temperature, etc.' and is usually 1 hour to 2 hours, preferably 3 hours to 7 2 hours. The target compound of each reaction after the completion of each of the above reactions is a reaction mixture obtained by a conventional method. For example, the reaction mixture is suitably neutralized, and after being removed by filtration in the presence of an insoluble system, an organic solvent which is not mixed with ethyl acetate is added, and after washing with water, the organic layer containing the objective compound is separated. After drying over anhydrous magnesium sulfate or the like, it is obtained by distilling off the solvent. The obtained target compound can be further purified by a usual method, for example, by recrystallization, re-sinking or chromatography. The step of producing the salt of the compound (1) of the present invention, which comprises extracting the concentrate of the reaction mixture of the compound (1) produced in each step, and further dissolving the compound (1) in a solvent of the appropriate -30- modified page 1314041 The acid used in the reaction by adding an acid in the liquid may, for example, be a mineral acid such as hydrogen fluoride acid, hydrochloric acid, hydrocyanic acid hydrosulfonic acid, hydrogen peroxide, nitric acid, perchloric acid, sulfuric acid or phosphoric acid. An organic acid salt of methanesulfonic acid, trifluoromethanesulfonic acid, lower alkanesulfonic acid of ethanesulfonic acid, benzenesulfonic acid, arylsulfonic acid of p-toluenesulfonic acid, succinic acid, oxalic acid, etc.; and organic acid saccharide of saccharin Amine compound. The acid system is usually used in an amount of from 1 equivalent to 10 equivalents, preferably from 1 equivalent to 5 equivalents. The solvent used in the reaction is not particularly limited as long as it does not inhibit the reaction. Examples thereof are ethers such as ether, diisopropane ether, tetrahydrofuran (THF), and dioxane, methanol, ethanol, and the like. Alcohols. The reaction temperature is -2 0 ° C to 5 01 :, preferably -1 0 ° C to 3 0 CTC. ·>1> The reaction time varies depending on the type of solvent to be used, temperature, etc., and is usually from 10 minutes to 1 hour. The resulting salt is isolated separately according to the usual method. Namely, the case of crystal precipitation is carried out by filtration, and in the case of water solubility, the separation is carried out by using a liquid separation of an organic solvent and water as an aqueous solution. The compound of the present invention is useful as an active ingredient of a pest control agent. For example, agricultural and horticultural fungicides exhibit excellent control effects against diseases caused by various plant pathogenic bacteria. Especially for rice blast, blight, bean, tomato, cucumber and kidney bean gray mold, sclerotinia, onion leukoplakia, wheat snow rot, powdery mildew, apple brown rot, spot stalk In addition, various diseases such as carbon plague of tea, brown spot disease of pear, black spot disease, black pox of grape, and black spot disease of citrus show excellent control effects. The compound of the present invention has an excellent therapeutic effect and can be prevented from being treated by post-infection treatment. When the compound of the present invention is used, it is the same as the previous pesticide preparation - 31- 1314041 v°, together with the auxiliary agent, various forms such as emulsion, powder, water and agent, liquid agent 'granule suspension preparation, etc. Preparation. When the preparations are actually used, they are used as they are or diluted with a diluent such as water to a predetermined concentration. The auxiliary agent to be used is exemplified by a carrier, an emulsifier, a suspending agent, a dispersing agent, a developing agent, a penetrating agent, a wetting agent, a viscous agent, a stabilizer, etc., and may be appropriately added as needed. The carrier used is a solid carrier and a liquid carrier, and the solid carrier may be starch 'sucrose, cellulose powder, cyclodextrin, activated carbon, soybean powder, wheat flour, rice hull powder, wood flour, fish meal, powdered milk, etc. Animal and plant powder; or, talc, kaolin, bentonite, organic bentonite, calcium carbonate, calcium sulfate, sodium bicarbonate, zeolite, diatomaceous earth, white carbon black, clay, alumina, vermiculite, ·>,, ' a mineral powder such as a sulfur powder, etc., the liquid carrier may be an animal or vegetable oil such as water, soybean oil, cotton oil or maize oil; an alcohol such as ethanol or ethylene oxide; a ketone such as acetone or methyl ethyl ketone; An ether such as decane or tetrahydrofuran; an aliphatic/aromatic hydrocarbon such as kerosene, kerosene, mobile paraffin, xylene, trimethylbenzene, tetramethylbenzene, cyclohexane or solvent naphtha; halogenation of chloroform, chlorobenzene, etc. a hydrocarbon; an acid amide such as dimethylformamide; an ester of ethyl acetate or a glyceride of a fatty acid; a nitrile such as propionitrile; a sulfur-containing compound such as dimethyl hydrazine; or N - methyl pyrrolidone or the like. The mass ratio of the compound of the present invention to the auxiliary agent is usually 0.05:99.95 to 90:10, preferably 0.2:99.8 to 80:20. The concentration or amount of the compound of the present invention varies depending on the target crop, the method of use, the form of the preparation, the amount of application, etc., and the effective ingredient of the stem and leaf treatment is generally 0.1 to 1000 ppm, preferably l~. 1 000 ppm, the soil treatment is generally 1 〇~i〇〇〇〇〇g/ha, preferably -32- 1314041 200~20000g/ha ° The compound of the present invention can be used with other pesticides as needed, for example, insecticidal Agents, acaricides, inducers, nematicides, fungicides, antiviral agents, herbicides, plant growth agents, etc., preferably used as insecticides, acaricides, nematicides or Fungicide. The insecticide, acaricide or nematicide used may be, for example, 〇_(4_ bromo-2-chlorophenyl)0-ethyl S-propylphosphoric acid vinegar ("generic name: horror flying pine") , 0-(2,2--chlorovinyl)anthracene, fluorene-dimethyl pity ester ("general name: dichlorvos", 0-ethyl hydrazine-{3 -methyl _4_(methyl thio) benzene Base} N_isopropyl guanidinium phosphate Lu (“gene name: fentansone), 0,0-dimethyl fluorene-(4·nitrom-tolyl) thiophosphate (general name: putty pine) , 0-ethyl 0-(4-nitrophenyl)phenylphosphonic acid thioester (general name: EPN), 0,0-diethyl fluorene-(2-isopropylmethylpyridine-4-yl)phosphoric acid Thioester (general name: Diannann), 0,0-dimethyl 0-(3,5,6-trichloro-2-pyridinidine) thiophosphate (general name: Taosson methyl), hydrazine, S-Dimethyl N-ethylphosphonium decyl thioxate (general name: chlorfenapyr), 0-(2,4-dichlorophenyl) fluorene-ethyl S-propylphosphonic acid disulfide 1 - ester (general name: thiomethicone) organophosphate ester compound; 1-naphthyl N-methylcarbamate (general name: carbaryl), ruthenium 2-isopropoxybenzene N -methylamine formate (a Name: PHC), 2-methyl-2-(methylthio)propanal oxime-methylaminoformamidine (general name: dextrometh), 2,3-dihydro-2,2-dimethyl Benzofuran-7-based N-methylamine formate (general name: Jiabaofu), dimethyl N,N'-[thiobis{(methylimino)carbenyloxy}]diethyl Alkyl imide thioester (general name: thiodike), second methyl N-(methylaminomethyl methoxy) thioethyl imidate (general name: nanet), hydrazine, hydrazine - two Methyl-2-methylaminomethyl methoxyimino-2-(methylthio)acetamide (general name: euthion), 2-(ethylthiomethyl) benzoquinone-methylamine Formate (general name: Affinity), 2-dimethylamine-5,6-dimethyl-33- 1314041 pyridine-4-yl N,N-dimethylamine formate (general name: Biga a 2,2-butylbenzene N-methylcarbamate (general name: BPMC) type of carbamate compound; S, S'-2-dimethylamine tri-methyl bis (sulfur Amino acid ester (general name: Pedan), N,N-dimethyl-1,2,3-trithia-5-amine (general name: thiophanate)-type detoxification compound; 2 ,2,2-trichloro-1,1-bis(4-chlorobenzene Ethyl alcohol (general name: large grams), 4-chlorobenzene-2,4'5-trichlorobenzene mill (general name: depleted) organochlorine-based compounds; double {tris(2-methyl-) 2-phenylpropyl)sulfide}oxide (general name: oxidized fenbutas) organometallic compound; (RS)-C-cyano-3-phenoxybenzyl (RS)-2- (4-Chlorophenyl)-3_methylbutyrate (“like name: Fenhuali”), 3-phenylphenoxybenzyl (1RS)-cis, trans- 3-(2,2-di Chlorovinyl)-2,2-dimethylcyclopropanecarboxylate (general name: baining), (RS)-a-cyano-3-phenoxybenzyl (1RS)-cis, anti -3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate (general name: 赛宁宁), (S)-a-cyano-3-phenoxybenzene Methyl (1R)-cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate (general name: chlorinated), (RS)-a-cyano -3-phenoxybenzyl (1RS)-cis, trans-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropane Vinegar (general name: Xeronine), 4-methyl-2,3,5,6-tetrafluorobenzyl-3-(2-chloro-3,3,3-trifluoro-:1-propene· Base)-2,2- Dimethylcyclopropanecarboxylate (general name · Tefluthrin), 2-(4-ethoxyphenyl)-2-methylpropyl 3-phenoxybenzyl ether (general name: Efenin compound pyrethroid compound; 1-(4-chlorophenyl)-3-(2,6-difluorobenzhydryl)urea (general name: Erfulong), 1-[ 3,5-Dichloro-4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenyl]-3-(2,6-difluorobenzhydryl)urea (general name: Chlorofluoroaslon), 1-(3,5-dichloro-2,4-difluorophenyl)-3-(2,6-difluorobenzhydryl)urea (general name: DeFulong) Benzofuramide-based compound; isopropyl (2E, 4E)-ll-methoxy-3,7,ll-trimethyl-2,4-dodecanol ester (general name: beauty Siping) -34- 1314041 Kindergarten-like compounds; 2 - tert-butyl-5-(4-tributylbenzylsulfonyl)-4-chloro-3(2H)-tetrahydrogen Tetrahydroponic ketone-based compound of the sorghum ketone (general name: Pythaben); tert-butyl 4-{(1,3-dimethyl-5-phenoxypyridin-4-yl) a pyrazole-based compound of methylaminohydroxymethyl}benzoate (general name: Fenpuff); 1-(6-chloro-3-D ratio Methyl)-N-nitro-tetragen imipenone-2 - a nitro compound such as a subunit moon female (general name: idadan); a dinitro compound, an organic sulfur compound, a urea compound, The triterpenic compound, the lanthanide compound, and other compounds may be 2-tert-butylimino-3-isopropyl-5-phenyl-3,4,5,6-tetrahydro-2H- 1,3,5-thiadipine-4-ketone (general name: buffing), trans-(4-chlorophenyl)-N-cyclohexyl-4-methyl-2-carbonylthiazolidinone-3 - Carboxylamidine (general name: hexahydrocarbyl), N-methylbis(2,4-dimethylphenylimidomethyl)amine (general name: Sanya), N'-(4-chloro-0 -tolyl)-N,N-dimethylformamidine (general name: atmosphere), (4-ethoxyphenyl)-{3-(4-fluoro-3-phenoxyphenyl)propene A compound of the formula (dimethyl) decane (general name: oxime). Further, the compound of the present invention may be used in combination with a microbial pesticide such as a BT agent or an entomopathogenic virus agent, an acamera mercapine, an anti-biobial substance of a hemoglobin crystal type, or the like. The bactericide used may be, for example, 2-anilino-4.methyl-6-(1-propyne)pyridine (general name: chlorpyrifos), 4,6-dimethyl-N-phenyl- 2 - chelate D-amine (general name: pyrene) pyrimidine amine compound; 1 - (4-chlorophenoxy 3,3 dimethyl-1- (1H-1,2,4-tri Oxazol-1yl)methylethyl ketone ("generic name: triammonium"), 1-(monophenyl-4-yloxy)-3,3-dimethyl-1-(1H,1,2 , 4-triterpene-1 yl)butan-2-ol (general name: than donut), 1MN_(4_chloro-2_trifluoromethylphenyl)_2-propoxyacetinylfee) Miso (general name: Saifu), 1-{2-(2,4-dichlorobenzyl)-4-ethyl-1,3-dioxalan-2-ylmethyl}-1Η- 1,2,4 - three squats (general name: amine base), .1-{2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxol-35 - 1314041 Cyclo-2-ylmethyl}-1Η-1,2,4-triazole (general name: Pkley), dichlorophenyl)pentyl}-1Η-], 2,4-triazole (general name) : Acetolide), bis(4-fluorophenyl)(methyl)(1H-1,2,4-triazole-buylmethyl)decane (general name: Fukunin), 2-(4- Chlorophenyl)-2-(1Η-1 , 2,4-triazol-1-ylmethyl)hexanenitrile ("generic name: microfouni"), (2RS, 3RS)-2-(4-chlorophenyl)-3-cyclopropyl-: 1-(1H-1,2,4-triazole-buyl)butan-2-ol (general name: Sec), (rs)-1-(4-chlorophenyl)-4,4- Dimethyl-3-(1Η-1,2,4-triazol-1-ylmethyl)pentan-3-ol (general name: Dekli), (RS)-2-(2,4 - two Chlorophenyl)-l-(lH-l,2,4-triazole-buyl)hexane-2-ol (general name: Fickley), (21^, 5 ft 3)-5-(2, 4-Dichlorophenyl)tetrahydro-5-(1Η-1,2,4-triazol-1-ylmethyl)-2-furanyl 2,2,2-trifluoroethyl ether (general name: Fickles), N-propyl-N-{2-(2,4,6-trichlorophenoxy)ethyl}imidazole-b-carboxamide (general name: poker pull), 2-(heart fluoride) An azole compound of phenyl)-1-(1Η-1,2,4triazol-1-yl)-3-trimethyldecylpropane-2·ol (general name: gram); 6-A a thialoporphyrin compound of the group -1,3-dithiazo [4,5,6] thiapipelin-2-ol (general name: detonation); manganese bis(dithiocarbamic acid) Ester) polymer (general name: mancozeb) 'zinc extension ethyl bis (disulfide) a urethane polymer (general name: zinc napu), zinc (lead lead) and manganese exoethyl bis(dithiocarbamate) (desenmanganese) wrong compound (general name: manganese zinc) Pu), a zinc bis(monomethyldithiocarbamate) exoethyl bis(dithiocarbamate) (general name · polycarbamate), zinc propylene bis (dithiocarbamate) a dithiocarbamate-based compound of a polymer (general name: methyl dexamethasone); 4,5,6,7-tetrachlorofluorenone (general name: Pyrex), tetrachloroisopropyl nitrile (general name: chlorinated ruthenium), organochlorine-based compound of the name of quintozene, and Qidusai; methyl 1-(butylaminomethylhydrazine) benzimidazole-2-ylamine Acid ester (general name: Free Lai-36- 1314041), dimethyl 4,4'-(〇_phenylene) bis(3_thioureacarboxylate) (general name: methylpoly , a benzimidazole-based compound of methylbenzimidazole-2-carbyl carbamate ("gene name: gram"); 3_chloro_N_(3_chloro-2,6_dinitro- 2 Pyridylamine compound of fluorotoluene)-5-trifluoromethyl-2-pyridinamine (general name: chlordiadine) a 1-cyanoacetamide compound of 1-(2-cyano-2-methoxyiminoethenyl)_3_ethylurea ("generic name: methyl papaverine); methyl N_( 2-methoxymethoxy)-indole (2,6-dimethylphenyl)-DL-alaninate (general name: statin) '2-methoxy-indole-(2-oxo-1) , 3-oxazolidin-3-yl)ethyl fluorenyl-2,6,-xylitol (general name: oxalox), (±)-α-2_chloro- Ν- (2,6 - Xylphenyl acetam) 7-butyrolactone (general name: Opris), methyl phenethyl ketone->^-(2,6-monomethylphenyl)-DL-alaninate ( General name: benzodiazepine), methyl ν-(2-furanyl fluorenyl)-fluorene-(2,6-dimethylphenyl)-DL-alaninate (general name: Fusula), (±) -α-[Ν-(3-chlorophenyl)cyclopropanecarboxamide]-r_butyrolactone (general name: tiara) benzoguanamine compound; N-dichlorofluoromethylsulfide-N, , N'-dimethyl-N-anilinosulfonate (general name: bacteriostatic) sulfenic acid-based compound; copper hydroxide ("generic name: copper hydroxide"), copper-8-hydroxyquinoline Copper compound of ester (general name: organic copper); 5-methylisoindole -3 -Alcohol (general name: hydroxyisoxazole) isoxazole-based compound; aluminum tris(ethylphosphonate) (general name · Fuqi aluminum), 〇_ 2,6-dichloro-p-toluene - 0 , 0-dimethyl thiophosphate (general name: tocopherylmethyl), s_ benzyl 0,0-diisopropane phosphorothioate, 0-ethyl s, s-diphenyl thio Phosphate ester, aluminum ethyl hydrogen phosphate ester organic phosphorus compound; N - (trichloromethylthio) cyclohexyl-4-ene-1,2-dicarboxyguanamine (general name: Gaptan), N- (l,1,2,2-tetrachloroethylthio)cyclohexyl-4-ene-I,2-dicarboxyguanamine (general name: diclofenac), N-(trichloromethylthio)anthracene The imine (general name: Sterilized Dan) n _halothane sulfane-37- 1314041 compound; N - (3,5-dichlorophenyl)-1,2-dimethylcyclopropane-1, 2 - Dicarboxyguanamine (general name: chlorpheniramine), 3-(3,5-dichlorophenyl)-N-isopropyl-2,4-dioxazolcarboxamide (general name: isopropanone), (RS)-3-(3,5-dichlorophenyl)-5-methyl-5-vinyl-1,3-oxazolidine-2,4-diol (general name: Free Kening) Dicarboxyimine compound; α,α,α-trifluoro-3′-iso Benzylimine-based compound of oxytoluidine (general name: futonine), 3'-isopropoxy-indole-toluidine (general name: chlorhexidine); hydrazine, Ν'-[hexahydropyridyl六-1,4-diylbis{(trichloromethyl)methylene}]dimethylamine (general name: 赛福宁) hexahydropyridinium compound; 2',4'-dichloro- 2-(3-pyridyl) acetophenone 0-methylindole (general name: fenfenol) pyridine compound; (±)-2,4'-dichloro-Q-(pyridin-5-yl) Benzyl alcohol (general name: fenrimyl), (±)-2,4'-difluoro-α-(1Η-1,2,4-triazole-buylmethyl)benzhydryl alcohol ( General name: Fudo Ai Song) methanol compound; (RS)-l-{3-(4-Tertiphenyl)-2-methylpropyl} hexahydropyrazine (general name: Fenpu Hexahydropyrazine compound; (±)-cis-4-{3-(4-t-butylphenyl)-2-methylpropyl b 2,6-dimethylmorpholine (general name) : Fenopinos) morpholino compounds; triphenylsulfonium hydroxides (general name: hydrazine hydroxylate), triphenyl hydrazine acetate (general name: hydrazine acetate) organotin compounds; 1 - (4 - Chlorophene Urea compound of 1-cyclopentyl-3-phenylurea (general name: benzilol); (E,Z)4-{3-(4-chlorophenyl)-3-(3,4- a cinnamic acid compound of dimethoxyphenyl)propenyl}molybdenum (general name: dimethoxyfolin); isopropyl 3,4-diethoxycarbonylcarbonyl (general name: sulphonate) Aniline-based compound; 3-cyano-4 -( 2,2-difluoro-1 ,3-benzodioxin-4-yl)pyrazole (general name: sylvestris), 3- (2',3'-Dichlorophenyl)-4-cyano-pyrazole (general name: Fenpuku) cyanopyrrole compound. -38 - 1314041 [Embodiment] The following examples, preparation examples and test examples are given to specifically illustrate the compounds of the present invention, but the present invention is not limited thereto. Example 1 NU-benzylcyclohexyl)quinoline-3-carboxamide (Compound No. 1-11) (Step A-1, A-2) 3-Quinolinic acid (150 mg, 0.9 mmol) The ear was dissolved in thionyl chloride (3. mM), heated for 1 hour, and the excess thionyl chloride was distilled off under reduced pressure, and the obtained residue was dried and dissolved in dichloromethane. (1 0.0 ml), then pyridine (0.3 ml) and 1-benzylmethylcyclohexylamine (102 mg, 0.54 mmol) were added and stirred at room temperature for 3 days. The reaction solution was poured into ice water, and the residue obtained by ethyl acetate extraction was analyzed by chromatography to give 86.5 mg (yield: 29%). Physical properties: oily. 1H-NMR (200MHz, CDC13) 6ppm: 1.4-1.80(8H, m), 2.04-2.32(2H, m), 3.23(2H, s), 5.58(1H, s), 7. 1 3 - 7.2 4 ( 5 H , m), 7.5 6-7.64 (lH, m), 7.7 5 - 7.8 9 ( 2 H , m), 8.13 (1H, d, J = 8.4 Hz), 8.41 (1H, d, J = 2.2Hz ), 9.16 (1H, d, J = 2.2 Hz). MS m/z: 344 (M + ), 30 1, 287, 253, 1 72, 1 5 6, 1 28, 1 〇i . Example 2 N - U - (4-Chlorobenzyl)cyclohexyl}quinoline-3-carboxycarbamide (Compound No. 1-17) (Step B-1) in 1-(4-chlorobenzyl)cyclohexanol ( To a solution of 1 mg (0.44 mmol) in acetic acid (1.0 ml), add quinoline-3-carbonitrile (103 mg, hydrazine, 67 mmol) and sulfuric acid (0.35 ml) and stir at room temperature 1 After the day, the residue obtained by extracting -39- 1314041 with ethyl acetate was purified by chromatography to give the title compound (1,43 mg (yield: 85 %). Physical properties: oily. 1 H-NMR (200MHz, CDC13) 5ppm : 1.4 8 - 1 . 6 6 ( 8 Η , m), 2.1 8-2.26(2Η, m), 3.18(2Η, s), 5.89(1Η, bs), 7.07 (2Η, d, J = 8.4Hz), 7.17(2H, d, J = 8.4Hz), 7.56(1H, t, J = 8.1Hz), 7.7 2-7.83 (2H, m), 8.07(1H, d , J = 8.4 Hz), 8.42 (1H, d, J = 2.3 Hz), 9. 13 (1H, d, J = 2.3 Hz). MS m/z : 3 7 8 (M + ), 343, 25 3 , 1 56, 1 28. φ Example 3 N-(1-Benzylcyclohexyl)quinoline-3-thioanisole (Compound No. 52) (C-1 step) N-(l-benzene Methylcyclohexyl)quinoline-3-carboguanamine (4 8.5 mg, 0.1 4 mmol) was dissolved in toluene (5.0), and Lawson's reagent (28.7 mg, 0.079 mmol) was added and heated to flow 3 After the lapse of the reaction, the reaction solution was poured into ice water, and washed with sodium hydrogencarbonate water, and the residue obtained by ethyl acetate extraction was analyzed by chromatography to give a target substance of 6.6 mg (recovery rate: 3 3 %). . φ Physical properties: oily. 1 H-NMR (200MHz, CDC13) 6ppm : 1.38-1.78(8H, m), 2.64-2.69(2H, m), 3.54(2H, s), 6.98(1H, br s), 7.2 4 - 7.2 7 ( 5 H , m), 7.54-7.61 (lH, m), 7.72-7.84 (2H, m), 8.08 (1H, d, J = 8.4 Hz), 8.20 (1H, br s), 9.11 (1H, d, J = 2.2 Hz). MS m/z: 3 60 (M + ), 269, 2 5 3, 189, 172, 154, 128, 104. In the same manner as in Examples 1 to 3, the following compounds were synthesized. . Example 4 - 40 1314041 Ν-U-Methylcyclohexyl)quinoline-3-carboxamide (Compound No. 1-]) Melting point: 9 8 - 1 0 0 °C. 1 H-NMR (200MHz, CDC13) δρρηι : 1.55(3H, s), 1.43 - 1.63 ( 8H, m), 2.1 2 - 2.2 4 (2 Η , m), 5.98(1H, S), 7.5 7 -7.65 ( 1 H, m), 7.7 6-7.84 ( 1 H, m), 7.9 1 (1 H, d, J = 8.2 Hz), 8. 1 5 ( 1 H, d, J = 8.2 Hz), 8.52 (1H, d, J = 2.0 Hz), 9.24 ( 1 H, d, J = 2.0 H z). MS m/z : 26 8 (M + ), 25 3, 225, 22 1, 1 7 3.

Example 5 Toluenemethyl)cyclohexyl}quinoline-3-carboxamide (Compound No. 1-12) Physical properties: oily. 1 H-NMR (200MHz, CDCI3) δρρηι : 1.4 6 - 1.6 7 (8 Η , m), 2.36(3Η, s), 2.30-2.40(2Η, m), 3.24(2Η, s), 5.83(1Η, Bs), 7.02-7. 1 3(4Η, m), 7.58(1Η, t, J = 7.0Hz), 7.7 3 - 7.8 5 (2 Η, m), 8.09( 1H, d, J = 8.4Hz) , 8.42 (1H, d, J = 2.3 Hz), 9.20 ( 1 H, d, J = 2.3 Hz). φ MS m/z : 35 8 (M + ), 275, 253, 1 56, 1 28. Implementation Example 6 N-{l-(3-Tolylmethyl)cyclohexyl}quinoline-3-carboxamide (Compound No. 1-13) Physical properties: oil. 1H-NMR (200MHz, CDC13) δρρηι : 1.51-1.65(8H, m), 2.22(3H, s), 2.22-2.26(2H, m), 3.18(2H, s), 5.57(1H, bs), 6.94 -7.11(4H, m), 7.59-7.62(lH, m), 7.75-7.87(2H, m), -41 - 1314041 8 . 1 3 ( 1 H, d, J = 8,4Hz), 8.40( 1 H, s), 9. 1 5( 1 Η, d, J = 2.0 Hz). MS m/z : 3 5 8 (M + ), 25 3, 1 5 6, 1 28. Example 7 N-{ 1-(4-Toluylmethyl)cyclohexyl}quinoline-3-carboxamide (Compound No. 1-14) Physical properties: oily.

'H-NMR (200MHz, CDC13) 6ppm : 1.2 5 - 1 . 6 5 ( 8 Η , m), 2.27(3H, s), 2.20-2.30(2H, m), 3.18(2H, s), 5.63( 1H, bs), 7.04(4H, bs), 7.59(1H, t, J = 8, 1Hz), 7.7 7 - 7.8 7 ( 2 H , m), 8. 1 1 (1 H, d, J = 8 , 4 Hz), 8.42 (1H, d, J = 2.3 Hz), 9.1 5 ( 1 H, d, J = 2.3 Hz). MS -m/z : 3 5 8 (M + ), 25 3, 1 5 6 , 1 28. Example 8 N-{l-(2-Chlorobenzyl)cyclohexyl}quinoline-3-carboxamide (Compound No. 1-15) Physical properties: oil.

1H-NMR (200MHz, CDC13) δρρηι : 1.4 3 - 1 . 7 0 ( 8 Η , m), 2.3 4-2.39(2Η, m), 3.41(2Η, s), 5.81(1Η, bs), 7.0 7 - 7.2 1 ( 3 Η , m), 7.35 (1Η, d, J = 7_6Hz), 7.62(1Η, d, J = 7, 8Hz), 7.76-7.89(2H, m), 8.13(1H, d, J = 8.7 Hz), 8.49 (1H, s), 9.21 (1H, s). MS m/z: 37 8 (M + ), 343, 253, 1 56, 1 28. Example 9 N-{ 1-( 3-Chlorobenzyl)cyclohexyl}quinoline-3-carboxamide (Compound No. 1-16) -42- 1314041 Physical properties: oily. ]Η-ΝΜΙΙ(200ΜΗζ, CDC13) δρρπι : 1.45-1_68(8H, m), 2. 1 7-2.27(2H, m), 3.20(2H, s), 5.71(1H, bs), 7.0 2 - 7 . 1 8 (4 H , m), 7 . 5 6 ( 1 H , t, J = 7.0 Hz), 7.7 2 - 7.8 4 ( 2 H , m), 8.07 (1H, d, J = 8.4 Hz), 8.37 (1H, d, J = 2.0 Hz), 9 . 1 4 ( 1 H , d, J = 2.0 Hz). MS m/z : 3 7 8 (M + ), 25 3, 1 7 3, 1 5 6, 1 28. Example 1 〇

N-(l-Benzylcyclohexyl)-6-methylquinolin-3-carboxamide (Compound No. 1-30) Physical properties: oily. 'H-NMR (200MHz, CDC13) 6ppm : 1.4 1 -1.6 9 ( 8 Η , m), 2.25-2.29(2H, m), 2.55(3H, s), 3.23(2H, s), 5.56(1H, Bs), 7. 1 3-7.23(5H, m), 7.6 1 (2H, d, J = 7.3Hz), 8.02( 1 H, d, J = 9.3Hz), 8.34( 1 H, d, J = 2.0 Hz), 9.06 ( 1 H, d , 3 = 2.3 Hz). MS m/z : 3 5 8 (M + ), 267, 1 70, 1 42, 1 1 5. Example 1 1

N-U-Benzylcyclohexyl)-8-methylquinoline-3-carboxamide (Compound No. 1-32) Physical properties: oily. 1 H-NMR (200MHz, CDCI3) δρρπι : 1.5 0 - 1.6 9 ( 8 Η , m), 2.21-2.3 1(2Η, m), 2.79(3Η, s), 3.22(2Η, s), 5.67(1Η , bs), 7. 1 3-7.23 (5Η, m), 7.46(1H, t, J = 6.9Hz), 7.5 9 - 7.7 0 (2 H , m), 8.39(1H, d, J = 2.0Hz ), 9. 1 8 ( 1 H, d, J = 2.0 Hz). MS m/z : 3 5 8 (M + ), 267, 1 87, 1 70, 1 42. Example 1 2 -43 - 1314041 N - (1-Benzylcyclohexyl)-8-methylquinolin-3-residual amine (Compound No. 3 8) Melting point: 1 0 1 - 1 0 3 °C. 1 H-NMR (200MHz, CDC13) 6ppm : 1 · 3 8 ( 3 Η, t, J = 7.7 Η z), 1.44- 1 , 69 (8H, m), 2.2 5 - 2.3 1 ( 2 H , m) , 3.23(2H, s), 3.30(2H, q, J = 7.7Hz), 5.58(1H, br s), 7. 1 2 - 7.2 5 (5 H , m), 7.52(1H, t, J = 7.6 Hz), 7.71 (1H, d, J = 7.6 Hz), 7.76 (1H, d, J = 7.6 Hz), 8.4 1 ( 1 H, d, J = 2.4 Hz), 9. 1 7 ( 1 H, d , J = 2 · 4 H z ). MS m/z : 37 2 (M + ), 281, 199, 184, 172, 156, 141, 128, 117, 9 1 , 8 1 , 65. Example 1 3 N-(l-Benzylcyclohexyl)-8-isopropylquinoline-3-carboxamide (Compound No. 400) Physical properties: amorphous. 1 H-NMR (200 MHz , CDC 13 ) 6 ppm : 1 · 3 9 (6 Η, d, J = 7 · OH z ), 1. 50- 1.70 (8H, m), 2.2 6 - 2.3 0 ( 2 H, m ), 3.24(2H, s), 4.33(1H, sep, J = 7.0Hz), 5.55(1H, br s), 7.1 4 - 7.2 2 ( 5 H , m), 7.57(1H, t, J = 7.7 Hz), 7.6 8-7.75 (2H, m), 8.43 (1H, d, J = 2.2Hz), 9.18(1H, d, J = 2.2Hz), MS m / z : 3 8 6 (M + ), 371,295,198,170,154,128,91, 81· Example 1 4 N-(1-Benzylcyclohexyl)-8-fluoroquinoline-3-carboxamide (Compound No. 1-44) Physical properties: Oily. 1 H-NMR (200MHz, CDC13) δρρπι : 1.4 5 - 1.6 9 ( 8 Η , m), -44 - 1314041 2 ' 2 5 - 2.2 9 (2 Η, m), 3 · 2 1 (2 Η , s ), 5 · 7 2 (] Η , bs ), 7. 1 4 - 7.2 3 (5 Η ' m), 7 . 3 9-7.54(2H, m), 8.62 (1H, d, J = 7.6Hz) , 8.37 (1H, d, J = 2.〇Hz), 9.13(1H, d, J = 2.0Hz). MS m/z: 362(M + ), 271, 174, 146,1 26. Example 5 NT-(1-Benzylcyclohexyl)-8-methoxyquinoline carboxamide (Compound No. 1 - 4 8 ) Melting point: 1 5 5 - 1 5 8 °C. 1 Η - NM R (2 OOMHz, CD C13) δpp m : 1 _ 4 5 - 1.6 6 ( 8 Η,m), 2.26-2.30(2H, m), 3.23(2Η, s), 4.10(3Η, s ), 5.52(1Η, bs), 7.1 2-7.20(6Η, m), 7.4 3 - 7.5 7 (2 Η , m), 8.39 (1Η, d, J = 2.3Hz), 9. 14( 1 Η, d, J=l_7 Hz). MS m/z: 374 (M + ), 283, 1 86, 1 72, 158, 128. Example 1 6 N - 1 -benzylcyclohexyl)-8 -methylthio Quinoline-3 -carboxamide (Compound No. 1 - 5 nickname) Melting point: 74-7 6 ° C. _ 1 H-NMR (200MHz, CDC13) 6ppm: 1.4 Ο - 1. 6 8 ( 8 Η , m), 2.24-2.28(2Η, m), 2.57(3Η, s), 3.22(2Η, s), 5.56 (1Η, br s), 7.13-7.22(5Η, m), 7.45(1Η, d, J = 7.7Hz), 7.53(1H, t, J = 7.7Hz), 7.60( 1 H, d, J = 7.7 Hz), 8.41(1H, d, J = 2.2Hz), 9.13(1H, d, J = 2.2Hz). MS m/z : 3 90(M + ), 3 3 3,299,218,202,185 , 1 74, 1 59, 140, 128, 115, 91, 81, 65. Example] 7 -45 - 1314041 N-(l-Benzylcyclohexyl)-8-methylquinoline-3-hydroxysulfuric acid Indoleamine (Compound No. 6) Physical properties: oily. 1 H-NMR (200MHz, CDC13) 5ppm : 1 . 3 9 - 1 . 7 Ο ( 8 Η , m), 2.23 -2.27 (2Η, m), 2.80(3Η, s), 3.23(2Η, s), 6.98(1Η, bs), 7.14-7.28(5Η, m), 7 · 4 6 - 7.5 9 ( 3 Η , m), 8.25(1Η, d, J = 2.3 Hz), 8.42 (1 Η, d, J = 2.3 Hz). MS m/z: 374 (M + ), 283, 203, 186, 172. Example 1 8 NU-benzylcyclohexyl) 8-fluoroquinoline-3-hydroxythioguanamine (Compound No. 1-71) Melting point: 1 6 5 - 1 6 9 ° C. 1H-NMR (200MHz, CDC13) 5ppm: 1.3 9 -1.7 1 ( 8 Η , m), 2.64-2.68 (2Η, m), 3.53(2Η, s), 6.99(1Η, bs), 7.2 2 - 7 .2 3 (5 Η , m), 7.3 9-7.5 5 (2Η, m), 7.61 (1Η, d, J = 7.6Hz), 8.42(1Η, d, J = 2.3Hz), 9.1 0( 1 H , d, J = 2.3Hz).

MS m/z : 37 8 (M + ), 287, 207, 1 90, 1 72. Example 1 9 N-(l-Benzylcyclopentyl)quinoline-3-carboxamide (Compound No. 1) -73) Melting point: 1 1 2 - 1 1 5 °C. W-NMRGOOMHz, CDC13) δρρηι : 1.72-2.1 8(8H, m), 3.28(2H, s), 5.81(1H, brs), 7. 1 7 - 7.2 4 ( 5 Η , m), 7.5 7 - 7.8 2 ( 2 Η , m), 7.85 (1H, d, J = 7.8 Hz), 8.12, (1H, d, J = 8.4 Hz), 8.39 (lH, d, J = 2.0 Hz), 9. 11 (1H , s). MS m/z : 3 3 0 (M + ), 302, 2 8 8, 26 1, 2 3 9, 1 7 3, 1 5 6. -46 - 1314041 Example 2 0 NU-Benzyl Cycloheptylheptyl)quinoline-3-carboxyguanamine (Compound No. 1-74) Melting point; 17-1 lg °c. 1H-NMR (200MHz, CDC13) 5ppm : 1.6 3 - 2.2 Ο (1 2 Η , m), 3.27(2Η, s), 5.64(1Η, brs), 7. 1 4 - 7.2 3 (5 Η , m) , 7, 5 8-7.83 (2Η, m), 7.88(1Η, d, J = 7.8Hz), 8.1 4,( 1 Η,d,J = 9.3 Η ζ ),8 · 4 3 (1 Η, d , J = 1.7Ηζ), 9.17(1Η, d, J = 2.0Hz). MS m/z : 35 8(M + ), 3 3 3, 30 1, 267, 1 73, 1 56, 1 28. Implementation Example 2 1 N-(l-Benzylcyclohexyl)-7-trifluoromethylquinoline-3-carboxamide (Compound No. 1-1 22) Physical properties: amorphous. iH-NMRpOOMHz, CDC13) δρριη: 1.44-1·70(8Η, m), 2·26-2.3 2(2Η, m), 3,2 2 (2 Η, s), 5 · 6 4 (1 Η, Brs), 1 1 2-7.24(5H, m), 7.75(1H, d, J = 8.6Hz), 7.97( 1 H, d, J = 8.6Hz), 8.40-8.43(2H, m), 9.19( 1H, d, J = 2.2 Hz). MS m/z: 41 2 (M + ), 393, 32 1, 224, 1 96, 1 69, 9 1,84. Example 2 2 N-(l-Benzene Methylcyclohexyl)-8-trifluoromethylquinoline-3-carboxamide (Compound 5, heptcode 1 -1 2 3) Physical properties: oily. H-NMRPOOMHz, CDC13) δρρηα : 1.38-1_70(8H,m), 2'25 -2.29 (2H, m), 3.23(2H, s), 5.62(1H, br s), 7. 1 2 - 7.2 5 (5 H , m), 7.67 ( 1 H, t, J = 7.9 Hz), 8.09 (1H, d, J = 7.9 Hz), 8.15 (1H, d, J ” ^7*9Hz), 8.54 (1H, d, J = 2.4 Hz), 9, 26 (1H, d, J 2.4 Hz) · 1314041 MS m/z : 41 2 (M + ), 3 93, 32 1,224,196,176,91. Example 2 3 N-{ 1-(4-Nitrophenylmethyl)cyclohexyl}quinoline-3-carboxamide (Compound No. 1 -〗 2 No. 6) Physical properties: oily. 1 H-NMR (200 MHz) , CDC13) 6ppm : 1.4 4 - 1.7 2 ( 8 Η,m ), 2.23-2.27(2H, m), 3.36(2H, s), 5.84(1H, bs), 7.31(4H, d, J = 8.7Hz ), 7.62(1H, t, J = 6 · 9 H z ), 7.7 7 - 7.9 0 (2 H , m), 8.0 3 ( 1 H, d, J = 8.7 Hz), 8.47 (1H, d, J = 2.0 Hz), 9.15 (1H, d, J = 2.4 Hz). MS m/z: 3 89 (M + ), 253, 1 56, 128. Example 24 N-(l-Benzylcyclohexyl) 8-Ethoxy-6,7-difluoroporphyrin-3-carboxamide (Compound No. 1-135) Physical properties: amorphous. 1 H-NMR (200 MHz, CDC13) 6 ppm : 1.4 0 -1 . 6 1 ( 8 Η , m), 1.49 (3H, t, J = 7.0Hz), 2.2 5 - 2.3 0 ( 2 H , m), 3.22(2H, s), 4.77(2H, q, J = 7.0Hz), 5.50(1H, brs), 7. 1 3 - 7.2 4 ( 5 H , m), 7.35( 1 H, dd, J = 2.0 Hz, 10.5 Hz), 8.34 (1H, d, J = 2.0 Hz), 9.0 B (1 H, d, J = 2.0 Hz). MS m/z : 424 (M + ), 423, 409, 333, 289 , 236, 208, 1 92, 180, 91. Example 2 5 N-(l-Benzylcyclohexyl)-6, 7, 8-trifluoroquinoline-3-carboxamide (Compound No. 1-136) No.) Melting point: 1 0 7 - 1 0 9 t. 1314041 】H-NMR (200MHz, CDC13) δρρηι : 1.38-1_72(8H,m), 2.25-2.3 1 (2H, m), 3, 22(2H, s), 5.50(1H, brs), 7. 1 3 - 7.2 5 ( 5 H , m), 7.46 ( 1 H, ddd, J = 2.3 Hz, 7.3 Hz, 9.6 Hz), 8.39 ( 1 H, d, J = 1,9 Hz), 9. 1 3 (1H , d, J = 1.9Hz). MS m/z : 39 8 (M + ), 35 5, 34 1, 3 23, 3 07, 2 1 0, 1 82, 1 62, 9 1 , 8 1 , 65 Example 2 6 N-{l-(2-Fluorobenzyl)cyclohexyl}salin-3-carboxamide (Compound No. 1 - 18) Physical properties: oily. 1H-NMR (200MHz, CDC13) 5ppm: 1. 3 5 - 1 . 6 9 ( 8 Η , m), 2.2 8-2.3 3 (2H, m), 3.28(2H, s), 5.75(1H, bs) , 6.9 3 - 7.0 3 (2 H , m), 7. 1 3-7.20(2H, m), 7.5 6 - 7.6 2 ( 1 H , m), 7.7 7 - 7.8 7 (2H , m), 8 . 1 1 (1 H, d, J = 8.4 Hz), 8.42 ( 1 H, d, J = 2.0 Hz), 9.1 7 ( 1 H, d, J = 2.0 Hz). MS m/z : 362 (M + ), 25 3, 1 5 6, 1 28, 1 09. Example 27 N-{l-(3-Fluorobenzyl)cyclohexyl}quinoline-3-carboxamide (Compound No. 19) Physical properties : Oily. 1H-NMR (200MHz, CDC13) 6ppm : 1.3 5 - 1.6 9 ( 8 Η , m), 2.24-2.27(2H, m), 3.23(2H, s), 5.76(1H, bs), 6.8 4 - 6.9 5 ( 3 H , m), 7.11-7.19(1H, m), 7.54-7.59(lH, m), 7.72-7.83(2H, m), 8.07(1H, d, J = 8.1Hz), 8.38(1H, s), 9.13(1H, s). MS m/z : 3 62 (M + ), 344,25 3, 1 5 6,128. 1314041 Example 2 8 Ν-{1-(4-fluorobenzyl) Cyclohexyl hydrazine-3-carboxyguanamine (Compound No. 20) Physical properties: oily. 'H-NMRGOOMHz, CDC13) Sppm : 1 · 4 5 - 1 . 6 8 ( 8 Η,m), 2 · 2 Ο - 2 _ 2 5 ( 2 Η , ιώ ), 3 · 1 9 ( 2 Η, s ), 5.7 1 ( 1 Η , bs ), 6 _ 9 1 (2 Η , d, J = 8.7 Hz), 7.11 (2Η, d, J = 8.7 Hz), 7.58 (1H, d, J = 8.1Hz) , 7.73-7.84(2H, m), 8.08( 1 H, d, J = 8.4Hz), 8.39( 1 H, d, J = 2.3Hz), 9.1 4( 1 H, d, J = 2.3Hz). MS m/z : 3 62 (M + ), 254, 1 7 3, 1 5 6, 1 28. Example 2 9 N-(l-Benzylcyclohexyl)-2-methylquinolin-3- Carboxyguanamine (Compound No. 27) Physical properties: oily. 1 H-NMR (200MHz, CDC13) δρρπι : 1.4 3 - 1.6 9 ( 8 Η , m), 2.20-2.26(2Η, m), 2.85(3Η, s), 3.23(2Η, s), 5.38(1Η, Bs), 7.25- 7.31(5Η, m), 7.47(1Η, d, J = 7.8Hz), 7.6 3 - 7.7 Ο (2 Η , m), 7.83(1Η, s), 7.95(1Η, d, J = 8.4 Hz). MS m/z: 358 (M + ), 339, 267, 1 70, 1 42. Example 3 0 N-(l-Benzylcyclohexyl)-4-methylquinoline-3 - Carboxyguanamine (Compound No. 28) Physical properties: oily. 'H-NMR (200MHz, CDCI3) 5ppm : 1.36-1.71(8H, m), 2.26- 2.3 1 (2H, m), 2.85(3H, s), 3.26(2H, m), 5.21(1H, br s ), -50- 1314041 7.2 3 - 7 . 3 4 ( 5 Η,m ),7 · 6 1 ( 1 Η,ddd,J = 1 · 5 Η z,7.0 Η z,8 · 4 Η z ), 7.74 (1H, ddcl, J = 1.5Hz, 7.0Hz, 8.4Hz), 8.07(2H, m), 8.74( 1 H, s), MS m/z : 3 5 8 (M + ), 3 3 9, 3 25, 30 1, 267, 1 87, 1 70, 142, 115, 9], 81, 65. Example 3 1 N-(l-Benzylcyclohexyl)-6-fluoroquinoline-3-carboxyindole Amine (Compound No. 1-42)

Melting point: 1 7 5 - 1 7 7 °C. 1 H-NMR (200MHz, CDCI3) δρρηι : 1.4 9 - 1.6 6 ( 8 Η , m), 2.24- 2.34(2Η, m), 3.23(2Η, S), 5.51(1Η, bs), 7.1 4 - 7.2 3 (5 Η , m), 7.47-7.60(2Η, m), 8. 1 2 - 8 . 1 7 (1 Η , m), 8.42 (1Η, d, J = 2.3Hz), 9.10(1Η, t , J = 2, 3 Hz). MS m/z : 3 62 (M + ), 306, 27 1, 1 74, 1 46. Example 3 2

N-(l-Benzylcyclohexyl)-8-hydroxyquinoline-3-carboxyguanamine (Compound No. 1 - 5 1) Physical properties: oily. H-NMRPOOMHz, CDC]3) δρρηι : 1.40- 1.7 3 (8H, m), 2.24- 2.34(2H, m), 3.25(2H, s), 5.61(1H, bs), 7.0 8 - 7.3 7 ( 6 Η , m), 7.42-7.47(lH, m), 7.5 2-7.57 (lH, m), 8.39(1H, s), 9.05(1H, s). MS m/z : 3 60(M + ), 269, 1 72, 1 44. Example 3 3 N-(l-Benzylcyclohexyl)-8-hydroxyquinoline-3-hydroxythioguanamine (Compound No. -51 - 1314041 Code No. 7 2) Physical properties : Oily. 1 H-NMR (200MHz, CDC13) 5ppm : 1.4 4 - 1.7 6 ( 8 Η , m), • 2.65-2.75 (2Η, m), 3.56(2Η, s), 7.00(1Η, bs), 7.2 Ο - 7.3 6 ( 7 Η , m), 7.5 1 (1 Η, t, J = 8. 1 Hz), 8. 1 5( 1 Η, s), 9.05( 1 Η, s). MS m/z : 376 (M + ), 269, 253, 1 88, 1 72. Example 3 4 N-(l-Benzylcyclohexyl)-6-fluoroquinoline-3-hydroxythioguanamine (Compound No. 1-69) ) Melting point: 1 9 0 - 1 9 3 °C. 1H-NMR (200MHz, CDC13) 6ppm : 1.3 9 -1.7 Ο ( 8 Η, m), 2.64-2.69 (2Η, m), 3.52(2Η, s), 7.07(1Η, bs), 7.2 3 - 7.2 9 (5 Η , m), 7.34-7.5 1 (2Η, m ), 7.9 5 - 8 . Ο 1 ( 1 Η , m), 8.06 (1Η, d, J = 2.3Hz), 9.00( 1 Η, d, J = 2.3 Hz). MS m/z : 37 8 (M + ), 207, 1 90, 1 72. Example 3 5 NU-propylcyclohexyl)quinoline-3-carboxamide (Compound No. 1- No. 3) Physical properties: oily. 1 H-NMR (270MHz, CDCI3) 5ppm : 0.93 (3H, t, J = 7.3Hz), 1.26- 1.63 (1 0H, m), 1. 8 7 - 1 . 9 3 (2 Η , m), 2.04 - 2.2 5 (2 Η , m), 5.39(1H, bs), 7.58-7.63(lH, m), 7.76-7.81(lH, m), 7·Β9(1Η, d, J = 8.2 Hz), 8.14(1H, d, J = 8.4Hz), 8.5 1 (1H, d, J = 2.3Hz), 9.24( 1 H, d, J = 2.3Hz). MS m/z : 296 (M + ), 25 3, 1 7 3, 1 56, 1 28, 1 0 1. Example 3 6 -52- 1314041 N-(]-Isobutylcyclohexyl)quinoxazole-3-carboxamide (Compound No. 1- No. 5) Physical properties: oily. !Η-ΝΜΙΙ(27 0ΜΗζ, CDC13) δρριη : Ο · 9 5 ( 6 Η, d, J = 6.7 Η ζ ), 1. 1 9-1 .89 (1 1 Η, m), 2 . Ο 4 - 2.2 8 (2 Η , m), 5.95 (1Η, bs), 7.56-7.63( 1 Η, m), 7.7 5 - 7.7 9 ( 1 Η , m), 7.8 Ο - 7.9 Ο (1 Η , m), 8 . 1 3 ( 1 Η, d, J = 8.4 Hz), 8.50 ( 1 Η, d, J = 2.3 Hz), 9.23 (1Η, d, J = 2.3 Hz). MS m/z : 3 10 (M + ), 253, 1 73, 1 56, 1 28, 1 0 1. Example 37 N-(l-allylcyclohexyl)quinoxazole-3-carboxamide (Compound No. 1-9) Physical Properties: Oily. H-NMR (270MHz, CDC13) δρρηι: 1 . 3 4 - 1.6 3 ( 8 Η , m), 2.01-2.27 (2Η, m), 2.68 (2Η, d, J = 7.6Hz), 5 . Ο 5 - 5 . Ο 9 (2 Η, m), 5.7 5 -5.8 8( 1 Η, m), 6.28(1Η, bs), 7.52(1Η, t, J = 8.2Hz), 7.68-7,79(2Η , m), 8 . Ο 5 (1 Η, d, J = 8 · 2 Η ζ), 8·45 (1Η, d, J = 2.0 Hz), 9.1 9 (ΙΗ, d, J = 2.0 Hz). MS m/z : 294 (M + ), 253, 173, 1 56, 1 28, 101 . Example 3 8 N-(l-propargylcyclohexyl)quinoline-3-carboxamide (Compound No. 1- No. 10) Physical properties: oily. 1 H-NMR (270MHz, CDC13) 5ppm : 1.2 Ο - 1 . 6 Ο ( 8 Η , m), 2.0 1 ( 1 Η, d, J = 2.8Hz), 2.3 1 - 2.3 5 ( 2 Η,m) , 2.89 (2Η, d, J = 2.8Hz), 6.4 1 (1Η, bs), 7.5 1 (1 H, t, J = 8.2Hz), 7.6 8 - 7.7 6 (2 Η , m), 8.04 ( 1 H, d, J = 8.2 Hz), 8.40 (1H, s), 9.20 ( 1 H, d, J = 1 , 6 Hz). 1314041 Example 3 9 N-(2-Benzylbicyclo[2.2.1 ]hept-2-yl)quinoline-3-carboxamide (Compound No. 1 - 7 5) Melting point: 〖5 2 - 1 5 4 °C. 1 H-NMR (270MHz, CDC13) δρριη : 1.2 9 - 2.2 Ο (8 Η, m), 2.38-2.45(2Η, m), 3.20(1Η, d, J=13.8Hz), 3.56(1Η, d, J = 13.8Hz), 5.57(1Η, bs), 7.1 9 - 7.2 1 (5 Η , m), 7.5 7 - 7.5 9 ( 1 Η , m), 7.7 8 - 7 · 8 6 (2 Η, m) , 8. 1 2 (1 Η, d, J = 8 · 7 Η ζ ), 8.2 9 (1 Η, d, J = 2.3 Hz), 9.03 (1Η, d, J = 2.3Hz). ® MS m/ z: 356(M + ), 265, 1 84, 1 56, 1 28, 1 1 5, 1 01 . Example 40 NU-Benzyl-3-methylcyclohexyl)quinoline-8-carboxamide (Compound No. 1-77) Physical properties: oily. 1H-NMR (500MHz, CDC13) δρριη: Ο . 8 8 - 1 . 7 4 (7 Η , m), 0.93 (3Η, d, J = 6.2Hz), 2.3 6 - 2.4 4 ( 2 Η , m), 3.18(1Η, d, J=13.7Hz), 3.23(1Η, d, J=13.7Hz), 5.61(1Η, bs), φ 7.15-7.27(5Η,m), 7.57 -7.60( 1 Η, m) , 7.7 5-7.7 8 ( 1 Η, m), 7.84 (1Η, d, J = 7.6Hz), 8.10(1Η, d, J = 8.2Hz), 8.39(1H, d, J = 2.1 Hz), 9.15 (1H, d, J = 2.1 Hz). MS m/z: 358 (M + ), 267, 1 56, 1 2 8. Example 4 1 NU-benzyl- 4-methylcyclohexyl)quinoline -3-carboxyguanamine (Compound No. 1-78) Physical properties: oily. -54- 1314041 1 H-NMR (500MHz, CDC13) 6ppm : 0.90 (3H, d, J = 6.9Hz), 1.06-1.65(7H, m), 2.40-2.42(2H, m), 3.21(2H, s ), 5.54(1H, bs), 7.15-7.24(5H, m), 7.60(1H, t, J = 8.2Hz), 7.78(1H, t, J = 8.2Hz), 7.86(1H, d, J = 8.2 Hz), 8. 1 2 ( 1 H, d, J = 8.2), 8.40 ( 1 H, d, J = 2. 1 Hz), 9. 15 (1H, d, J = 2. 1 Hz). MS m/z: 3 5 8 (M + ), 267, 1 56, 1 28. Example 42 N-[ 1-(4-aminophenylmethyl)cyclohexyl]quinoline-3-carboxamide. (Compound No. 1 - 1 2 8 5 Tiger) Physical properties: 1 7 9 - 1 8 0 °C. 1H-NMR (270MHz, CDC13) 5ppm: 1.23-1.68 (8H, m), 2.25 -2.30 (2H, m), 3.10 (2H, s), 3.54 (2H, bs), 5.57 (1H, bs), 6.55 (2H, d, J = 8.4 Hz), 6.94 (2H, d, J = 8 · 4 H z), 7 · 5 7 · 7.6 3 (1 H, m), 7.7 6-7.82 (lH, m), 7.88(1H, d, J = 8.2Hz), 8. 13(1H, d, J = 8.6Hz), 8.42(1H, d, J = 2.0Hz), 9.1 7( 1 H, d, J = 2.0Hz MS m/z : 359 (M + ), 253, 1 87, 1 56, 1 28, 1 06. Example 43 φ N-[l-(2-methoxybenzyl)cyclohexyl]quina Porphyrin-3-carboxyguanamine (Compound No. 1 - 1 3 7) Physical properties: oily. 1 H-NMR (270MHz, CDC13) 5ppm : 1.5 7 - 1 . 7 0 ( 8 Η , m), 2.46-2.50(2H, m), 3.21(2H, s), 3.77(3H, s), 6.30( 1H, bs), 6.86-7.21(3H, m), 7, 60(1H, t, J = 8.6Hz), 7.79(1H, t, J = 8.6Hz), 7.87(1H, d, J = 8.6Hz ), 8 · 1 4 (1 H, d, J = 8 · 6 H z), 8.44 ( 1 H, d, J = 2.0 Hz), 9. 1 6 ( 1 H, d, J = 2.0 Hz). -55- 1314041 MS m/z : 3 74 (M + ), 25 3, 202, 1 56, 1 2 8, 1 2 1, 1 0 1. Example 44 'N-[l-(3-methoxy) Benzomethyl)cyclohexyl]quinoline-3-carboxamide (Compound • Number 1 · 1 3 8) Physical properties: oily. 1 H-NMR (270MHz, CDC13) 5ppm : 1. 19-1 .65(8H, m), 2.20-2.35(2H, m), 3.18(2H, s), 3.61(3H, s), 5.96(1H , s), 6.70-6.75(3H, m), 7.11(1H, t, J = 7.9Hz), 7.49(1H, t, J = 7.6Hz), 7.67-7.72(2H, m), 7.98(1H, d, J = 8.2 Hz), 8.31(1H, s), 9,14(1H, s). MS m/z : 374(M + ), 253, 202, 1 56, 1 28, 1 2 1, 1 01 . Example 4 5 N-[I -(4-Methoxybenzyl)cyclohexyl]quinoline-3-carboxamide (Compound No. 1-139) Physical properties: oily. 1H-NMR (270MHz, CDC13) 5ppm : 1.5 0 - 1 . 6 9 ( 8 Η , m), 2.25-2.29 (2Η, m), 3.17(2Η, s), 3.73(3Η, s), 5.54(1Η , bs), 6.76(2Η, d, J = 8.6Hz), 7.07(2H, d, J = 8.6H2), 7.5 8 - 7.6 4 ( 1 H , m), 7.7 6-7.8 3 (lH, m) , 7.88(1H, d, J = 8.2Hz), 8.14(1H, d, J = 8.6Hz), 8.43(1H, d, J = 2.3Hz), 9.17(1H, d, J = 2.3Hz). MS m/z : 374 (M + ), 253, 202, 1 56, 1 28, 1 2 1, 1 01. Example 4 6 1 [1-(2-hydroxybenzyl)cyclohexyl]quinoline-3 _ Carboxyguanamine (Compound No. 1-146) Physical properties: oily. -56- 1314041 *Η-ΝΜΚ(270ΜΗζ, DMSO-d6) δρριη : 1 . 4 5 - 1 . 7 5 ( 8 Η , m ), 2.54-2.68(2Η, m), 3.27(2Η, s), 6.75 -6.95(2Η, m), 7.00-7,20(3Η, τη), 7.4 5 - 7.5 2 ( 1 Η , m), 7.6 2 - 7.6 8 ( 1 Η , m), 7.75(1Η, d, J = 8.2Hz), 7.90(1Η, d, J = 8.6Hz), 8.52( 1 Η, d, J = 2.1 Hz), 9.15(1H, d, J = 2.1Hz). MS m/z : 360(M + ), 253, 1 73, 1 56, 1 28, 1 07. Example 47

N-[1-(3-Hydroxybenzyl)cyclohexyl]quinoline-3-carboxamide (Compound No. 1 -1 4 7) Physical properties: oily. j-NMRmOMHz, DMSO-d6) δρρπι : 1.4 Ο -1.7 1 (8 Η , m), 2,40-2.48(2Η, m), 3.21(2Η, S), 6.64(1Η, s), 6.7 3 - 6.8 4 (3 Η , m), 7.1 6( 1 Η, t, J = 7.6Hz), 7.62(1Η, t, J = 8.2Hz), 7.76(1Η, t, J = 8,2Ηζ), 7.88( 1Η, d, J = 8.2Hz), 8.00( 1 H, d, J = 8.6Hz), 8.48(1H, s), 9.04(1H, s). MS m/z : 360(M + ), 253, 1 88, 1 73, 1 56, 1 28, 1 01.

Example 4 8 N-[l-(4-Hydroxybenzyl)cyclohexyl]quinoline_3-carboxamide (Compound No. 1-148) Physical properties: oil. 'H-NMR (270MHz, DMSO-d6) 6ppm : 1. 1 7 -1 . 6 5 ( 8 Η , m), 2.17-2.29 (2Η, m), 3.31(2Η, s), 6.60(2Η, d , J = 8.2Hz), 6.91(2Η, d, J = 8.2Hz), 7.61(1H, s), 7.67(1H, t, J = 8.6Hz), 7.84(1H, t, J = 8.6Hz), 8.06(2H, d, J = 8.6Hz), 8.67(1H, d, J = 2.3Hz), 9. 1 5( 1H, d, J = 2.3Hz). -57- 1314041 MS m/z : 3 60 (M + ), 25 3,156,128,107. Example 49 N-[ 1-(3-Bromobenzyl)cyclohexyl]quinoxa-3-carboxyguanamine (Compound No. 156) Physical Properties: 8 2 - 8 4 °C. 1H-NMR (270MHz, CDC13) 6ppm : 1.3 0 - 1 . 7 9 ( 8 Η , m), 2.1 8-2.34(2Η, m), 3.21(2Η, s), 5.56(1Η, bs), 7.04- 7 .1 2(2Η, m), 7.28-7.3 7 (2Η, m), 7.6 0 ( 1 Η,t,J = 8.4 Η ζ ),7.7 9 ( 1 Η,t,

J = 8.4 Hz), 7.88 (1 Η, d, J = 8.4 Hz), 8. 1 3 ( 1 H, d, J = 8.4 Hz), 8.4 1 (1 H, d, J = 1, 8 Hz), 9.16 (1H, d, J = 1.8 Hz). MS m/z: 425 (M + + 2), 423 (M + ), 253, 1 56, 1 28, 1 01. Example 5 0 N-[l -(3-Cyanobenzyl)cyclohexyl]quinoline-3-carboxamide (Compound No. 1 - 165) Physical properties: oily. 'H-NMR^OMHz, CDC13) δρρηι : 1.2 8- 1.77 (8H, m),

2. 1 6-2.34(2H, m), 3.28(2H, s), 5.79(1H, bs), 7.29(1H, t, J = 7.6Hz), 7.36-7.50(3H, m), 7.58(1H , t, J = 8.2Hz), 7.77(1H, t, J = 8.2Hz), 7.85(1H, d, J = 8.2Hz), 8.08( 1 H, d, J = 8.2Hz), 8.42( 1 H , d, J = 2.3Hz), 9.1 3 ( 1 H, d, J = 2.3Hz). MS m/z : 3 69(M + ), 25 3, 1 7 3, 1 56, 1 2 8, 1 0 1. Example 5 1 Ν·[ 1-(2-Trifluorotoluenemethyl)cyclohexyl]quinoline-3-carboxamide (Compound No. b 1 7 3) Melting point: 1 3 7 - 1 4 2. (:. -58- 1314041) H-NMR (270MHz, CDC13) δρρπι : 1 _ 3 4 - 1 · 7 9 ( 8 Η,m), 2.23-2.3 6(2Η, m), 3.47(2Η, s) , 5.84(1Η, bs), 7.2 5 - 7.3 7 ( 3 Η , m), 7.57-7.66(2Η, m ), 7.7 6 - 7.8 8 ( 1 Η , m), 7.91(1Η, d, J = 8.2 Hz), 8.15 (1Η, d, J = 8.6Hz), 8.54( 1 Η, d, 3 = 2.1 Hz), 9.25( 1 H, d, J = 2.1 Hz). MS m/z : 412(M + ), 393, 355, 253, 1 56, 1 28, 1 0 1. Example 5 2 N-[l-(3-Trifluorotoluenemethyl)cyclohexyl]quinoline-3-carboxamide ( Compound No. 1-174) Calling point: 1 0 3 - 1 0 5 ° C. 1H-NMR (270MHz, CDC13) 5ppm: 1·28-1·76(8Η, m), 2.1 8-2.3 1 ( 2Η, m), 3.29(2H, s), 5.78(1H, bs), 7.2 9 - 7.3 7 (2 Η , m), 7.41-7.47(2H, m), 7.54(1H, t, J = 8.2Hz ), 7.6 9 - 7.8 2 (2 Η, m), 8.04 (1H, d, J = 8.6Hz), 8 · 3 5 (1 H,d,J = 2.1 H z),9 · 1 3 (1 H , d, J = 2.1 Hz). MS m/z : 412 (M + ), 393, 253, 1 56, 1 28, 1 0 1. Example 5 3 φ N-[l-(4-trifluorotoluene) Methyl)cyclohexyl]quinoline-3-carboxamide (Compound No. 1 - 175) Physical properties: oily. 1 H-NMR (270MHz, CDC13) 5ppm : 1 . 3 Ο -1.7 2 ( 8 Η,m), 2.1 8-2.32(2Η, m), 3.30(2Η, s), 5.74(1Η, bs), 7.27(2Η, d, J = 7.9Hz ), 7.47 (2Η, d, J = 7.9Hz), 7.58(1Η, t, J = 8.4Hz), 7.72-7.8 8(2H, m), 8.09(1H, d, J = 8.6Hz), 8.38( 1H, d, J = 2.3Hz), 9.176(1H, d, J = 2.3Hz). -59- 1314041 MS m/z : 4 1 2(M + ), 3 5 5, 25 3, 1 5 6, 1 2 8, 1 0 1. Example 5 4 N-(1-Ethynylcyclohexyl)quinoline-3-carboxamide (Compound No. 1-182) Physical properties: oily. 1H-NMR (270MHz, CDC13) 5ppm : 1.2 8 - 1 . 3 7 ( 1 Η , m), 1.63-1.84 (5Η, m), 1.94-2.03 (2Η, m), 2.29-2.35 (2Η, m) , 2.51 (1Η, t, J = 1.5Hz), 6.36(1H, bs), 7.5 7 - 7.6 3 ( 1 H , m), 7.77-7.90(2H, m), 8.13(1H, d, J = 8.5 H2), 8.56(1H, s), 9.23-9.25( 1H, d , J = 2.0Hz). MS m/z : 279(M+ 1 ), 265, 250, 224, 1 67, 1 56, 1 49. Example 5 5 N-(1-Benzylcyclobutyl)quinoline-3-carboxamide (Compound No. 1-191) Melting point: 1 6 1 -1 6 4 t:. h-NMROOOMHz, CDC13) δρρηι : 1.8 4 - 2 . Ο 8 ( 2 Η , m), 2.29-2.3 5 (2Η, m), 2.3 9 - 2.4 4 (2 Η , m), 3.33(2Η, s) , 6.25(1Η, bs), 7.17-7.27(5Η, m), 7.5 9 (1 Η,t,J = 7.6 Η ζ), 7.8 2 (1 Η,ddd, J= 1.4, 7.6, 8.2Hz), 7.84 (1Η, d, J = 7.6Hz), 8. 10(1Η, d, J = 8.2Hz), 8.44(1Η, d, J = 2.1Hz), 9. 12(1H, d, J = 2. 1 Hz). MS m/z: 3 1 6 (M + ), 225, 1 5 6, 1 28. Example 5 6 N-(l-Benzylcyclobutyl)-4-methylquinoline-3 - Carboxylamamine (Compound No. 1-193) Melting point: 1 6 0 - 1 6 2 t:. 1314041 'Η-ΝΜΙΙ(500ΜΗζ, CDC13) δρριη : 1.9 8 - 2 _ 1 2 (2 Η,m ), 2.3 1-2.37(2Η, m), 2.4 2 - 2.4 7 (2 Η , m), 2.70( 3Η, s), 3.36(2Η, s), 6.20( 1 Η, bs), 7.24-7.33(5Η, m), 7.54(1Η, t, J = 8.2Hz), 7.68(1 Η, t, J = 8.2 Hz), 7.9 1 ( 1 Η, d, J = 8.2 Hz), 7.94 ( 1 H, d, J = 8.2 Hz), 8.55 ( 1 H, s). MS m/z : 330(M + ), 239, 1 87, 1 70, 1 42. Example 5 7 N-(l-Benzylcyclopentyl)quinoline-3-hydroxythioguanamine (Compound No. 1-194)

Melting point: 1 0 5 - 1 0 8 °C. 1 H-NMR (270MHz, CDC13) 6ppm : 1.7 6 - 1 . 8 8 (4 Η , m), 2.01-2. 12(2Η, m), 2.3 4 - 2.4 4 (2 Η , m), 3.60( 2Η, S), 7.18(1Η, bs), 7, 28-7.3 0( 5 Η, m), 7.5 4 - 7.6 0 ( 1 Η , m), 7.7 2 - 7.8 2 (2 Η , m), 8.08 (1Η, d, J = 8.4Hz), 8. 1 6( 1 Η, d, J = 2.3Hz), 9.06( 1 Η, d, J = 2.3Hz). MS m/z : 346(M + ) , 1 89, 172, 1 58, 1 28, 1 1 7, l〇1 · Example 5 8 # N-(l-Benzylcycloheptyl)quinoline-3-hydroxythioguanamine (Compound No. 1 No. -195) Physical properties: oily. 1H-NMR (270MHz, CDC13) 5ppm : 1.5 0 - 1 . 7 5 ( 8 Η , m), 1 , 97-2.06(2Η, m), 2.3 9 - 2.44 (2 Η , m), 3.60 (2Η, s), 7.11(1Η, bs), 7.22-7, 29(5Η, m), 7.5 5 - 7.5 7 ( 1 Η , m), 7.7 2 - 7.8 2 ( 2 Η , m), 8.07 ( 1 Η, d, J = 8.4 Hz), 8.22 ( 1 Η, d, J = 2, 3 Hz), 9. 1 1 (1 Η, d, J = 2.3 Hz) _ -61 - 1314041 MS m/z ·· 374 ( M + ), 1 86, 172, 1 55, 1 28, 1 1 7, 104. Example 5 9 N-(l-Benzyl-3-methylcyclohexyl)-4-methylquinoline-3 - Carboxyguanamine (Compound No. 1 - 1 9 7) Melting point: 1 6 8 - 1 7 1 °C. 'H-NMRiSOOMHz, CDC13) 6ppm : 0.8 9 - 1.7 6 (7 Η , m), 0.93 (3Η, d, J = 6.2Hz), 2.3 5 - 2.4 8 (2 Η, m), 2.77(3H, s ), 3. 19(1H, d, J=13.1Hz), 3.27(1H, d, J=13.1H2), 5.46( 1 H, bs), 7.23-7.33(5H, m), 7.53-7.57(1 Ή, m), 7.66-7.69(1H, m), 7.91(1H, dd, J = 2.1, 8.2Hz), 7.97(1H, d, J = 8.2Hz), 8.69(1H, s). MS m/ z : 3 72(M + ), 3 5 6, 28 1, 267, 1 87, 1 70, 1 42. Example 6 0 N-(l-Benzyl-4-methylcyclohexyl)_4-A Quinoquinoline-3-carboxamide (Compound No. 1 - 189; one non-image isomer) Physical properties: oily. 1 H-NMR (500MHz, CDC13) 6ppm : 0 · 9 2 (3 Η, d, J = 6.2 Hz), 1.08- 1.26(2H, m), 1.4 2 - 1.4 8 (3 H , m), 1.64 - 1.6 6 ( 2 H , m), 2.3 9-2.42 (2H, m), 2.79(3H, s), 3.23(2H, s), 5.40(1H, bs), 7.22-7, 3 2 (5H, m ), 7.56 (1H, t, J = 8.2 Hz), 7.69 (1H, t, J = 8.2 Hz), 7.96 (1H, d, J = 8.2 Hz), 7.99 (1H, d, J = 8.2), 8.70 ( 1 H, s). MS m/z : 372 (M + ), 28 1, 267, 1 87, 1 7 0, 1 42. Example 6 1. N-(l-Benzyl-4-methyl Cyclohexyl)_4_methylquinoline-3_carboxyguanamine (Chemical-62- 1314041 Compound number 1 -1 9 8; the other non-image isomer) Physical properties: oily. 1 H-NMR (500 MHz, CDC13) 6 ppm : 1. Ο 3 ( 3 Η, d, J = 6 · 2 Η z), 1.25- 1.44 (2H, m), 1.66-1.75 (5H, m), 2_23- 2·26(2Η, m), 2.7 5 ( 3 H,s ), 3 · 3 5 ( 2 H,s ), 5 · 4 2 ( 1 H,bs ), 7 · 2 3 - 7.3 3 (5 H ,m ), 7.57(1H, t, J = 8.2Hz), 7.70(1H, t, J = 8.2Hz), 7.99(1H, d, J = 8.2Hz), 8.00(1H, d, 1 = 8.2) , 8.62 (1H, s). MS m/z: 372 (M + ), 28 1 , 267, 1 87, 1 70, 1 42. Example 62 # N-[l-(3-fluorobenzyl) Cyclohexyl]-4-methylquinoline-3-carboxyguanamine (Compound No. 1 - 199) Physical properties: oily. 'H-NMROOOMHz, CDC13) δρρπι : 1.3 3- 1.70(8H, m), 2.25- 2.28(2H, m), 2.85(3H, s), 3.27(2H, s), 5.26(1H, bs), 6.92 -7.00(2H, m), 7.06(1H, d, J = 7.6Hz), 7.24 - 7.2 8 ( 1 H , m), 7.61(1H, t, J = 8.2Hz), 7.74( 1H, t, J = 8.2Hz), 8.06(1H, d, J = 8.2Hz), 8.07(1H, d, J = 8.2Hz), 8.74( 1 H, s). · MS m/z : 376(M + ), 3 57, 267, 187, 170, 142. Example 63 N-[l-(4-fluorobenzyl)cyclohexyl]-4-methylquinoline-3-carboxamide (Compound No. 1-200) Physical properties: amorphous. ^-NMRCSOOMHz, CDCI3) 6ppm : 1.3 2 - 1 . 7 0 ( 8 Η , m), 2.24-2.26(2H, m), 2.84(3H, s), 3.24(2H, s), 5.21(1H, bs ), 6.98-7.01(2H, m), 7.22-7.26(2H, m), 7.73(1H, t, J = 8.2Hz), -63- 1314041 7 ·75( 1 H, t, J = 8.2Hz) , 8.07 ( 1 Η, d, J = 8.2 Hz), 8.08 (1Η, d, J = 8.2Hz), 8.74(1Η, s). MS m/z : 3 7 6(M + ), 267, 1 8 7,1 70, 1 42. Example 64 N-(l-Benzylcyclohexyl)-8-methoxyquinoline-3-hydroxythioguanamine (Compound code 1 - 2 0 1) Physical properties: 1 6 8 - 1 7 2 °C. 1 Η - NMR ( 2 7 0 Μ H z, CDC 13) δ ppm : 1.2 2 - 1 . 6 9 ( 8 Η,m), 2-6 3 -2.67 (2Η, m), 3.53(2Η, s) , 4.07(3Η, s), 6.98(1Η, bs), 7 ·〇8(1Η, d, J = 7,8Hz), 7.20-7.28(5Η, m), 7.38(1Η, d, j = 7.8Hz ), 7.49( 1 Η, t, J = 7.8Hz), 8.20(1H, d, J = 2.3Hz), 9-〇6(lH, d, J = 2.3Hz). MS m/z : 390(M + ), 2 1 9, 202, 1 85, 1 72, 1 59, 129. Example 65 N-[l-(3-Fluoro-4-toluomethyl)cyclohexyl]quinoline-3-carboxamide (Compound No. 1 - 2 0 2) Melting point: 1 5 4 - 1 5 6 °C. 1 H-NMR (500MHz, CDC13) 5ppm: 1. 3 1 -1.4 4 (1 Η , m), 1 -44-1.56(4Η, m), 1. 6 6 - 1.6 8 ( 3 Η, m), 2. 1 9(3Η, S), 2-25-2.27(2Η, m), 3.19(2Η, S), 5.66(1Η, bs), 6.8 2 - 6.8 3 ( 2 Η , m), 7.01 (1Η , t, J = 7.4Hz), 7 · 5 9 ( 1 Η, t, J = 8 · 0 Η ζ ), 7 · 7 8 (1 Η, ddd, J = 1. 1 , 6.9, 8.6 Hz), 7.85(1Η, d, J = 8.0Hz), 8. 1 0( 1 H, d, j = 8.6Hz), 8.42( 1 H, d, J = 2.3Hz), 9. 1 6( 1 H, d , J = 2.3 Hz). MS m/z : 3 7 6 (M + ), 3 5 8, 25 3, 1 5 6, 1 28. Example 66 -64 - l3U〇4i N-[l-(5 -Win-2-methylmethyl)cyclohexyl]indole-3-residamine (Compound No. 1-204) Physical properties: oily. ^-NMRCSOOMHz, CDC13) 5ppm : 1.2 3 - 1.2 5 ( 1 Η , m), 1 · 4 3 - 1 · 5 1 (4 Η,m ),1 · 6 7 - 1 · 7 1 ( 3 Η,m ), 2.3 2 (3 Η, s), 2·37-2.39 (2Η, m), 3.23(2Η, s), 5.86(1Η, bs), 6.79(1Η, td, J=:2.9, 8.0Hz) , 6.85(1H, dd, J = 2.9, 1 0.3 H z ),7 · 0 8 (1 H,dd, J = 6.3, 8.0Hz), 7.58(1H, ddd, J=ll, 6.9, 8.0Hz) , 7.77 (1H, ddd, J = 1. 1 , 6.9, 8.0 Hz), 7.85 (1H, d, J = 8.0 Hz), 8.10 (1H, d, · J = 8.〇Hz), 8.45 ( 1H, d, J = 2.3 Hz), 9 · 2 0 (1 H, d, J = 2.3 Hz). MS m/z : 376 (M + ), 3 57, 253, 156, 128. Example 67 Ν-[ 1·(3-Fluoro-4-toluomethyl)cyclohexyl]-4-methylquinoline-3-carboxyguanamine (Compound No. 1-67) Physical properties: oily. 1 Η - NM R ( 5 0 0 Μ H z , CDCI3) δρρηι : 1 . 3 Ο - 1 . 3 7 (1 Η , m), 1.42-1.56 (4 Η, m), 1.68-1.70 (3Η, m ), 2.23(3Η, S), · 2.23 -2.27 (2Η, m), 2.86(3H, S), 3.22(2Η, s), 5.22(1Η, bs), 6.92-6.95(2Η, m), 7.10 (1Η, t, J = 7.4Hz), 7.62(1Η, ddd, J=ll, 6.9, 8.6Hz), 7.74(1Η, ddd, J=ll, 6.9, 8.0Hz), 8.07(1H, d, J = 8.0 Hz), 8.08 (1H, d, J = 8.0 Hz), 8.77 (1H, s). MS m/z : 3 90 (M + ), 3 7 1, 267, 1 87, 1 70, 1 42 Example 6 8 N-[l-(5-fluoro-2-toluomethyl)cyclohexyl]-4-methylquinoline-3-carboxamide (Compound No. 1-210) -65- 1314041 Physical properties : Oily. 'H-NMR (500MHz, CDCI3) 5ppm : 1.2 2 - 1 . 2 8 ( 1 Η , m), 1.43 - 1 .5 5 (4Η, m), 1.63-1.74 (3 Η, m), 2.3 6( 3Η, s), 2.3 6 -2.3 9 (2Η, m), 2.8 1 (3Η, s), 3.26(2H, s), 5.79(1H, bs), 6.83(1H, td, J = 2.9, 8.0Hz ), 7.00(1H, dd, J = 2.9,9 · 7 H z ), 7. 1 1 ( 1 H, dd, J = 6.3, 8.0 Hz), 7.55 (1H, ddd, J= 1.7, 6.9, 8.6 Hz), 7.69 ( 1H, ddd, J=1.7, 6.9, 8.6 Hz), 7.95 (1H, d, J = 8.6 Hz), 7.97 (1H, d, J = 8.6 Hz), 8.79 (1H, s). MS m/z : 390 (M + ), 267, 1 87, 1 70, 1 42. · Example 6 9 N-[l-(2, 3-difluorobenzyl)cyclohexyl]quinolin-3 - Carboxylamamine (Compound 5 Tiger Code 1 - 2 1 1) Melting point: 1 4 2 - 1 4 5 °c.

'H-NMRCSOOMHz, CDCh) 5ppm : 1. 3 5 -1.7 1 ( 8 H, m), 2.28-2.3 1 (2H, m), 3.34(2H, s), 5.65(1H, bs), 6.8 8 - 7.0 1 (3 H , m), 7.6 2-7.65 (lH, m), 7.8 0 - 7.8 3 ( 1 H , m), 7.91 (1H, d, j = 8.2Hz), 8.16(1H, d, J = 8.9 Hz), 8.4 8 (1 H, s), 9 · 1 9 (1 H, s). MS m/z : 3 80 (M + ), 25 3, 1 56, 1 28. Example 7 N-[l-(2,5-difluorobenzyl)cyclohexyl]quinoline-3-carboxamide (Compound No. 1 - 2 1 2) Melting point: 1 3 6 - 1 3 8 °C 〇 'H-NMR (500MHz, CDCh) 5ppm : 1 . 3 2 - 1 . 7 1 ( 8 Η , m), 2·28-2.30(2Η, m), 3.29(2Η, S), 5.68(1Η, bs ), 6.8 3 - 6.9 1 ( 2 Η , m), 6.94-6·99 (1Η, m), 7.63 (1Η, ddd, J II 1.4, 6.9, 8.2 Ηζ), -66- 1314041 7.8 1 (1 H , ddd, J= 1 .4, 6.9, 8.2Hz), 7.91 (1H, d, J = 8.2Hz), 8.15(1H, d, J = 8.2Hz), 8.49(1H, d, J = 2.1Hz) , 9.19 (1H, d, J = 2.1 Hz). MS m/z: 3 80 (M + ), 253, 1 56, 1 28. Example 7 1 Ν-Π-(3, 4-difluorobenzene Base) cyclohexyl]quinoline-3-carboxamide (Compound No. 1 - 2 1 3) Melting point: 80-83 ° C. 1 Η - NMR (5 0 Ο Μ H z, CD C13) δ ppm : 1 · 3 1 -1 · 7 0 (8 H , m), 2.23- 2.26 (2Η, m), 3.22(2Η, s), 5.59(1Η, bs), 6.6 5 - 6.6 8 ( 1 Η, m), 6.97-7.05 (2Η, m), 7.6 2 - 7.6 5 ( 1 Η , m), 7.82 (1Η, ddd, j= 1.4, 6.9, 8.2 Hz), 7.91 (lH, d, J = 8.2 Hz), 8.15 (1H, d, J = 8.2 Hz), 8.45 (1 H, d, J = 2.1 Hz), 9.17 (1H, d, J = 2.1 Hz). MS m/z: 3 80 (M + ), 25 3, 1 5 6, 1 28. Example 7 2 Ν-Π-(3, 5-difluorobenzyl)cyclohexyl]quina Porphyrin-3-carboxyguanamine (Compound No. 1-214) Melting point: 5 5-57 °C. 1 H-NMR (500MHz, CDC13) 6ppm: 1. 3 4 - 1 .7 0 (8 Η , m), 2.24- 2.27(2Η, m), 3.25(2Η, s), 5.61(1Η, bs), 6.6 3 - 6.6 7 ( 1 Η, m), 6.70-6.7 1 (2Η, m), 7.63 (1Η, t, J = 8.2Hz), 7.81(1H, t, J = 8.2Hz), 7.91 (1H, d, J = 8.2 Hz), 8. 15 (1H, d, J = 8.2 Hz), 8.46 (1H, d, J = 2.1 Hz), 9.17 (1H, d, J = 2.1 Hz). MS m/z : 3 80(M + ), 25 3,1 5 6, 1 28. Example 7 3 -67 - 1314041 N-[](2,3-Difluorobenzyl)cyclohexyl]-4-methylquin Porphyrin-3-carboxyguanamine (Compound No. 1-2 19) Physical properties: amorphous. 1 H-NMR (500MHz, CDC13) 5ppm : 1 . 3 1 -1.7 1 (8 Η , m), 2.26-2.29 (2Η, m), 2.86(3Η, s), 3.36(2Η, s), 5.30( 1Η, bs), 7.0 1-7 . 1 1 (3Η, m), 7.6 1 - 7.6 4 (1 Η , m), 7.7 4 - 7.7 7 ( 1 Η , m), 8.08 (1H, d, J = 8.2 Hz), 8. 1 0 ( 1 H, d, J = 8.9 Hz), 8.79 ( 1 H, S). MS m/z : 3 94 (M + ), 267, 1 87,170,1 42, 1 27. Example 74 N-[l-(2,5-Difluorobenzyl)cyclohexyl]-4-methylquinoline-3-carboxamide (Compound No. 1 - 220) Physical properties: oily Things. j-NMROOOMHz, CDCI3) δρριη : 1.33-1.71(8H, m), 2.25-2.28(2H, m), 2.8 8 ( 3 H,s ),3.3 0 ( 2 H,s ),5 · 3 5 (1 H,bs), 6.8 8-6.92(lH, m), 6.9 7 - 7.0 2 ( 1 H , m), 7.0 4 - 7.0 7 ( 1 H , m), 7.62 (1H, ddd, J= 1.4, 6.9 , 8.2Hz), 7.75(1H, ddd, J= 1.4, 6.9, 8,2Hz), 8.08( 1 H, d, J = 8.2Hz), 8.09( 1 H, d, J = 8.2Hz), 8.83( 1H, s). MS m/z: 394 (M + ), 267, 1 87, 1 70, 1 42, 1 27. Example 7 5 Ν-Π-(3, 4-difluorobenzyl) ring Hexyl]-4-methylquinoline-3-carboxyguanamine (Compound No. 1-221) Physical properties: oily. • H-NMRCSOOMHz, CDC13) δρριη : 1, 33-1.71(8H, m), 2.23-2.25(2H, m), 2.83(3H, s), 3.24(2H, s), 5.31(1H, bs), 1314041 6.97-7.01(lH, m), 7.06-7.11(2H, m), 7.6 1(1H, ddd, J=1.4, 6.9, 8.2Hz), 7.74(1H, ddd, J=1.4, 6.9, 8.2Hz ), 8.04 (1H, d, J = 8.2 Hz), 8.06 (1H, d, J = 8.2 Hz), 8.73 (1H, s). MS m/z : 394 (M + ), 267, 1 87, 1 70, 1 42, 1 27. Example 7 6 N-[l-(3,5-Difluorobenzyl)cyclohexyl]-4-methylquinoline-3-carboxamide compound number 1 - 222 ) Melting point: 1 95- 1 97 °C. 1H-NMR (500MHz, CDC13) 6ppm: 1·34-1·72(8Η, m), 2.25 -2.26 (2Η, m), 2.8 1 (3Η, s), 3,26(2Η, s), 5.49 (1 Η, bs), 6.68-6.72( 1 Η, m), 6.8 1 - 6.8 4 (2 Η , m), 7.58 (1Η, dd, J = 6.9, 8.2Hz), 7.71(1Η, dd, J = 6.9, 8.2 Hz), 7.98 ( 1 Η, d, J = 8.2 Hz), 8.01 (1Η, d, J = 8.2Hz), 8.72(1H, s). MS m/z : 394(M + ), 267, 1 87, 170, 142, 1 27. Example 7 7 N-[l-(2,3-Dichlorobenzyl)cyclohexyl]quinoline-3-carboxamide (Compound No. 1 - 223) ) Melting point: 8 1 - 8 4 °C. 1 H-NMR (500MHz, CDC13) 6ppm: 1.2 8 -1.7 1 ( 8 Η , m), 2.34-2.37 (2Η, m), 3.4 9 (2 Η, s), 5 · 7 1 (1 Η, bs ), 7.0 2 ( 1 Η, t, J = 7.6 Hz), 7.12 (1H, dd, J = 1.4, 7.6 Hz), 7.32 (1H, dd, J = 1.4, 7.6 Hz) 7.64 (lH, ddd, J = 1 .4, 6.9, 8.2 Hz), 7.82 (1H, ddd, J= 1.4, 6.9, 8.2 Hz) 7.91 (lH, d, J = 8.2 Hz), 8. 1 6 ( 1 H, d, J = 8.2 Hz), 8.50 (1H, d, J = 2, 1 Hz), 9.23 (1H, .d, J = 2. 1 Hz). MS m/z : 4 1 2 (M + ), 377, 267, 253, 1 70, 1 5 6, 1 28. -69- 1314041 Example 7 8 N-[l-(2,5-Dichlorobenzyl)cyclohexyl]quinacin-3-carboxamide (Compound Number) 1-224) Melting point: 139-14TC. H-NMR (500MHz, CDC13) 6ppm : 1.42-1.71(8H,m), 2.32-2.35(2H, m), 3,40(2H, s), 5.67(1H, bs), 7.12(1H, d , J = 8.9Hz), 7.24-7.30(2H, m), 7, 63(1H, t, J = 7.6Hz), 7.82(1H, t, J = 7.6Hz), 7.92(1H, d, J = 8.2Hz), 8. 1 6( 1H, d, J = 8.2Hz), 8.50(1H, s), 9.23(1H, s). Φ MS m/z : 41 2(M + ), 377, 267, 253, 1 56, 1 28. Example 7 9 N-[l-(2,3-Dichlorobenzyl)cyclohexyl]-4-methylquinoline-3-carboxamide (Compound No. 1-231) No.) Physical properties: oily. 1 H-NMR (500MHz, CDC13) 5ppm: 1.2 9 -1 . 7 1 ( 8 Η , m), 2.3 1-2.34 (2Η, m), 2.59 (3Η, s), 3.51(2Η, s), 5.37 (1Η, bs), 7.14(1Η, t, J = 8.2Hz), 7.32(1H, dd, J = 2.1, 8.2Hz), 7.37(1H, φ dd, J = 2.1, 8.2Hz), 7.70(1H , ddd, J=1.4, 6.9, 8.2Hz), 7.7 8(1H,ddd, J=1.4, 6.9,8.2Hz), 8.10(1H,d, J = 8.2Hz), 8.11(1H, d, J = 8.2 Hz), 8.96 (1H, s). MS m/z: 426 (M + ), 39 1, 267, 187, 170, 142. Example 80 Ν-Π-(2, 5-dichlorobenzyl) Cyclohexyl]-4-methylquinoline-3-carboxyguanamine (Compound No. 1 - 232) Physical properties: oily. -70- 1314041 1 H-NMR (500MHz, CDC13) 5ppm : 1.2 5 -1 . 7 1 ( 8 H, m), 2.28-2.3 1 (2H, m), 2.91 (3H, s), 3.42 (2H, s), 5.46(1H, bs), 7.1 4( 1 H, d, J = 8.2Hz), 7.30(1H, d, J = 8.2Hz), 7.40(1H, s), 7.62(1H, t, J = 8.2 Hz), 7.75 (1H, t, J = 8.2 Hz), 8.08 (2H, d, J = 8.2 Hz), 8.90 ( 1 H, s). MS m/z : 426 (M + ), 39 1 , 267, 253, 1 70, 1 56, 142. Example 8 1 N-[l-(3-Thienylmethyl)cyclohexyl]quinoline-3-carboxamide (Compound No. 1 - 2 3 5) # Physicality: oily. 1H-NMR (500MHz, CDCI3) 5ppm : 1.35-1.68(8H, m), 2.25-2.28(2H, m), 3.28(2H, s), 5.67(1H, bs), 6.90(1H, d, J = 4.8 Hz), 6.96 (1H, d, J = 2.7 Hz), 7.18 (1H, dd, J = 2.7, 4.8 Hz), 7.60 (1H, t, J = 8.2 Hz), 7.78 (1H, t, J = 8.2 Hz), 7.86 (1H, d, J = 8.2 Hz), 8.12 (1H, d, J = 8.2 Hz), 8.40 ( 1 H, d, J = 2.1 Hz), 9. 15 (1H, d, J = 2.1 Hz). MS m/z: 350 (M + ), 25 3, 1 78, 1 56, 1 28. · Example 82 N-{l[l-(3-methyl-3-ethynyl) Methyl]cyclohexyl μ quinolin-3-carboxyguanamine (Compound No. 1-23 No. 6) Melting point: 1 05-108 °C. W-NMROOOMHz, CDC13) δρριη : 1 _ 3 2 -1 · 6 8 ( 8 Η,m), 2.19(3H, s), 2.34-2.36(2H, m), 3.38(2H, s), 5.81(1H , bs), 6.78(1H, d, J = 5.5Hz), 7.02(1H, d, J = 5.5Hz), 7.61(1H, ddd, J=1.4, 6.9, 8.2Hz), 7.80(1H, ddd, J = 1.4, 6.9, 8.2 Hz), -71 - 1314041 7.90 (1H, d, J = 8.2 Hz), 8.14 (1H, d, J = 8.2 Hz), 8.52 (1H, d, J = 2.1 Hz), 9.25 (1H, d, J = 2.1 Hz), MS m/z: 3 64 (M + ), 25 3, 1 92, 1 5 6, 1 28. Example 8 3 N-{[l-(2, 5-Dimethyl-3-thiophene)methyl]cyclohexylfluorene-3-carboxyguanamine (Compound No. 1-23 No. 7) Physical properties: oily.

1H-NMR (5 00MHz, CDC13) 6ppm : 1.31 - 1,68(8H, m), 2.30(6H, s), 2.3 3-2.3 9(2H, m), 3.06(2H, s), 5.74(1H , bs), 6.41(1H, s), 7.6 1 (1 H, ddd, J= 1.4, 6.9, 8.2Hz), 7.80( 1 H, ddd, J= 1.4, 6.9, 8.2Hz), 7.88(1H, d, J = 8.2 Hz), 8.14 (1H, d, J = 8.2 Hz), 8.45 ( 1 H, d, J = 2.1 Hz), 9.21 (1H, d, J = 2.1 Hz). MS m/z : 37 8(M + ), 253, 206, 1 56, 128. Example 84 N-ll-[(3-methyl-4, 5-dihydroisoxazolyl-4-yl)methyl]cyclohexyl Quinoline _3_carboxamide (Compound No. 1 - 238)

Physical properties: oily. H-NMR (270MHz, CDC13) δρρηι : 1.33-1_73(8H,m), 1 ,96(3H, s), 1.97-2.13(1H, m), 2.3 7 - 2.5 2 ( 3 H , m), 2.62 (1H, dd, J = 8.6, 16.8 Hz), 3,05 (1H, dd, J = 9.9, 16.8H2), 4.67-4.84 (lH, m), 6.40 (1H, bs), 7.60 (1H, t, J = 7.6Hz), 7.7 2-7.84( 1 H,m), 7.90(1H, d, J = 7.6Hz), 8.13(1H, d, J = 8.2Hz), 8.54(1H, d, J = 2. 1 Hz), 9.28 (1H, d, J = 2.1 Hz). MS m/z : 35 1 (M + ), 267, 253, 1 73, 1 56, 1 28, 1 0 1. Example 8 5 -72- 1314041 NU-[(3-Methylisoxazolyl-4-yl)methyl]cyclohexyl)quinoline-3-carboxamide (Compound No. 1-23 No. 9) Physical properties: oily Things. 'H-NMR (270MHz, CDC13) δρρπι : 1.2 6 - 1 . 7 3 ( 8 Η, m), 2.12(3Η, s), 2.20-2.34(2Η, m), 3.41(2Η, s), 5.83( 1Η, s), 6.38(1Η, bs), 7.49-7.5 8 ( 1 Η, m), 7.6 7 - 7.8 3 (2 Η , m), 8.04( 1 Η, d, J = 8.2Hz) ( 8.43( 1 Η, S), 9. 1 5( 1 Η, S). MS m/z : 349 (Μ + ), 25 3, 1 Τ3, 1 5 6, 1 28, 1 0 1. Example 8 6 # Ν_Π·[(benzothiazole·3-yl)methyl]cyclohexyl}quinoline-3-carboxamide (Compound No. 1-240) Physical properties: oily. ^-NMRCSOOMHz, CDC13) 6ppm : 1 . 3 2 - 1.7 0 ( 8 Η , m), 2.38-2.41 (2Η, m), 3.51(2Η, s), 5.68(1Η, bs), 7.12(1Η, s), 7.28-7.34(2Η, m) , 7.5 8 - 7.6 2 ( 1 Η , m), 7.7 7 - 7.8 6 (3 Η, m), 7.9 1 (1 Η, d, J = 7.6Hz), 8.13(1 Η, t, J = 7.6Hz ), 8.3 2 - 8.3 4 ( 1 Η , m), 9. 1 5(1Η, S). φ MS m/z: 400(Μ + ), 25 3, 228, 1 5 6, 1 2 8. Implementation Example 8 7-[1-(1-Naphthylmethyl)cyclohexyl]quinoline-3-carboxamide (Compound No. 1 - 2 4 1) Physical properties: oil. 'H-NMR (500MHz, CDCI3) δρρπι : 1.4 3 - 1 . 6 8 ( 8 Η , m), 2.40-2.43(2Η, m), 3.71(2Η, s), 5.58(1Η, bs), 7.33- 7.44(4Η, m), 7.60(1Η, t, J 7.6Hz), 7.74(1Η, dd, J = 2.1, 6.9Hz), -73- 1314041 7 · 7 7 - 7.8 3 ( 3 Η , m) , 8.16(1Η, d, J = 8.2Hz), 8.2 7 - 8.2 9 (2 Η , m), 9·13(1Η, d, J = 2.lHz). MS m/z · 394(M ), 253, 222, 156, 128. Example 8 8 N-[l-(2-Naphthylmethyl)cyclohexyl]quinacin-3-carboxamide (Compound No. 1-242) Melting point: 1 3 0 - 1 3 3 °C. 'H-NMRCSOOMHz, CDCls) δρρπι : 1.3 7 - 1.6 9 ( 8 H, m),

2.3 1-2.34(2H, m), 3.41(2H, s), 5.53(1H, bs), 7.32(1H, dd, J = 1.4, 8.2Hz), 7.39-7.41 (2H, m), 7.5 8 - 7.6 3 (2 H , m), 7.66-7.68 (lH, m), 7.70 (1H, d, J = 8.2H2), 7.7 6 - 7.8 2 (3 H, m), 8. 1 4 ( 1 H, d, J = 8.2 Hz), 8.37 (1H, d, J = 2.1 Hz), 9.2 0 ( 1H, d, J = 2. 1 Hz). MS.m/z : 3 94(M + ), 25 3, 222, 1 56, 1 28. Example 8 9 N-[l-(3-Pyridylmethyl)cyclohexyl]quinoline-3-carboxamide (Compound No. 1-244) φ Physical properties: oily. 1 H-NMR (500MHz, CDCI3) 5ppm : 1.3 7 - 1.6 9 ( 8 Η , m), 2.24-2.26(2H, m), 3,28(2H, s), 5.62(1H, bs), 7. 13(1H, d, J = 7.6Hz), 7. 14(1 H, d, J = 7.6Hz), 7.48(1H, d, J = 8.2Hz), 7.62(1H, t, J = B.2Hz ), 7 · 8 1 (1 H , t, J = 7.6 H z), 7.9 0 (1 H, d, J = 8.2 Hz), 8.42-8.43 (2H, m), 8.46 ( 1 H, d, J = 2.1 Hz), 9.17 (1H, d, J = 2.1 Hz). MS m/z : 346 (M + ), 25 3, 1 7 3, 1 56, 1 28. 74- 1314041 Example 90 N-[ L-(l-styryl)cyclohexyl]quinoline-3-carboxyindoleamine compound number 2 4 6) Physical properties: oily. 1 H-NMR (27 0 MHz, CDC13) 6 ppm: 1.2 8 - 1 . 8 0 ( 8 Η , m), 2.45 -2.50 (2H, m), 5.13 (1H, s), 5.50 (1H, s), 5.96 (1H, bs), 7.2 3 -7.26 (5H, m), 7.60 (1H, t, J = 7.9Hz), 7.79(1H, t, J = 7.9Hz), 7.87(1H, d, J = 7.9Hz ), 8.13 (1H, d, J = 7.9Hz),

8.4 1 (1 H, d, J = 2.0 Hz), 9.1 6 ( 1 H, d, J = 2.0 Hz). MS m/z : 356 (M + ), 25 3, 184, 156, 128. Examples 9 1 N-[ 1-(1-Phenylethyl)cyclohexyl]quinoline-3-carboxamide (Compound No. 247) Physical properties: oily. 'H-NMR (500MHz, CDCI3) δρριη : 1.27-1.71(8H, m),

1 -39(3H, d, J = 6.9Hz), 2.20-2.23.(1H,m), 2.4 6 - 2.4 8 ( 1 H , m), 3.79(1H, q, J = 6.9Hz), 5.56( 1 H, bs), 7.2 0 - 7.2 7 ( 5 H , m), 7.60 (1H, t, J = 7.6Hz), 7.76-7.80(lH, m), 7.86( 1H, d, J = 7.6Hz) , 8. 1 2( 1 H, d, J = 7.6Hz), 8.37(1H, d, J = 2.1 Hz), 9. 14(1H, d, J = 2. 1Hz). MS m/z : 3 5 9 (M + ), 25 3, 1 7 3, 1 5 6, 1 28. Example 9 2 N-[ 1-(1-Phenylethyl)cyclohexyl]-4-methylquinoline-3- Carboxyguanamine (Compound No. 1 - 2 4 8) Melting point: 1 7 5 - 1 7 8 °C. -75- 1314041 1H-NMR (270MHz, CDC13) 5ppm : 1.29-1.71(8H, m), 1.42 (3H, d, J = 7.3Hz), 2.2 4 - 2.3 9 ( 2 H , m), 2.79 (3H , s), 3.84(1H, q, J = 7.3Hz), 5.48(1H, bs), 7.1 9 - 7.3 1 (5 H , m), 7.51-7.58(1H, m), 7.6 5 - 7.7 ] ( 1 H , m), 7.98 (1H, d, J = 8.2 Hz), 7.99 (1H, d, J = 8.6 Hz), 8.67 (1H, m). MS m/z : 373 (M + ), 268, 187,171,142. Formulation Example 1 Powder The compound of Example i (1_0 parts by mass), Dolly A (alkyl ether phosphate, manufactured by Nippon Kayaku Co., Ltd., 4 parts by mass), Kabra Kus #80-D (white carbon black, manufactured by Yanyeyi Pharmaceutical Co., Ltd., 1.5 parts by mass), calcium carbonate (made by Adachi Lime Co., Ltd., 质量·5 parts by mass) and official clay wind ratio (primary phase furnace) After mixing with the material Co., Ltd., 32.1 parts by mass), it is pulverized with the black sapporo KII-1 (hammer mill) and the Fujiwa Talu Co., Ltd., and the mass of the pulverized material is A 1.5-fold amount of DL clay Kaihe (manufactured by Kaihe Co., Ltd.) was added to obtain a powder DL. Formulation Example 2 φ Emulsion The compound of Example 2 (10 parts by mass) was dissolved in xylene (manufactured by Wako Pure Chemical Industries, Ltd., 40 parts by mass) and DMSO (manufactured by Wako Pure Chemical Industries, Ltd., 35 parts by mass). In the mixed solution, P arak ο 1 KPS (a mixture of an anionic surfactant and a cationic surfactant, and 25 parts by mass of Nippon Emulsifier Co., Ltd.) was added to the solution to obtain an emulsion. Formulation Example 3 Water and Agent - 76 - 1314041 Revision Page f (T gas / Compound of Example 3 (1 part by mass), Kabrescus Well 80-D (10 parts by mass), Fruit Noro GL05 (Polymer Vinyl alcohol, Nippon Synthetic Chemical Co., Ltd. - 2 parts by mass, Newquaru 291PG (dioctylsulfosuccinate sodium salt, manufactured by Japan Emulsifier Co., Ltd., 0.5 parts by mass), new杷 塔 ( (straight alkylbenzene sulfonate sodium salt, manufactured by Daiichi Pharmaceutical Co., Ltd., 5 parts by mass), Radiation Light #200 (burned into diatomaceous earth), manufactured by Showa Chemical Industry Co., Ltd., 10 quality (Parts) and Η differential (kaolin clay), manufactured by K.K., Ltd., 71.5 parts by mass) were thoroughly mixed and pulverized with black sapporo ΚΙΙ-1 to obtain water and a liquid. Formulation Example 4 Granules The compound of Example 4 (2 parts by mass), sodium tripolyphosphate (manufactured by Mitsui Chemicals, Inc., 2 parts by mass), and Amiguru NO. 1 (dextrin, Japanese starch chemical limited stock) Company system, 1.5 parts by mass), kaolin (manufactured by Hanshun Mining Co., Ltd., 25 parts by mass) and Kalupi 600 (calcium carbonate, made from Lili Co., Ltd., 69.5 parts by mass), using semi-circular extrusion The press (not made by Wu Ta Lu Co., Ltd., screen 〇.9mm p) was extruded and granulated. The obtained granules were dried in a shed type dryer (manufactured by Tabay Co., Ltd., PERFECT OVEN PS-222 type, 60 ° C), and sieved to 600 to 118 ° quot; m to obtain a viscous agent. Test Example 1 Rice blast prevention test (therapeutic effect) In the potted culture test plants (rice variety: Xingfeng) at the 3rd to 4th leaf stage, the pathogen suspension was sprayed and inoculated at room temperature of 2〇~23°C. The pot is placed in the inoculation chamber to promote the onset. The compound of the present invention was dissolved in a dimethyl hydrazine-methanol mixed-77- 1314041 solution (volume ratio: 7/3), and a dispersion liquid containing 300 ppm of the compound of the present invention was adjusted to be uniformly dispersed in the pot. The incidence of the disease 7 days after the inoculation was investigated. The test was carried out in 2 rows. In addition, the degree of the disease was visually observed by the naked eye, and it was judged by the following criteria, and it was represented by the 4th order of 0 to 3. The degree of disease is 〇%: there is no disease at all. 1: The incidence is less than 40% of the untreated area. 2: The incidence is 40% or more and less than 80%. 3: The incidence is more than 80%. The results of this test are Example 1 (Compound No. 1 - 1 1 ), Example 2 (Compound No. 1-17), Example 3 (Compound No. 1-52), and Example 5 (Compound No. 1 -1 2) ), Example 6 (Compound No. 1 - 1 3 ), Example 7 (Compound No. 1 - 1 4 ), Example 9 (Compound No. 1 -1 6 ), Example 1 (7 Compound No. 1 - 3) 0), Example 1 1 (Compound No. 1 - 3 2 ), Example 1 4 (Compound No. 1 - 4 4, Example 1 7 (Compound No. 1 - 6 7 ), Example 1 8 (Compound No. 1 - 71), Example 19 (Compound No. I-73), Example 20 (Compound No. 1-74), Example 24 (Compound No. 135), Example 26 (Compound No. 1-18), Example 27 ( Compound number 1 - 9), Example 28 (Compound No. 1-20), Example 30 (Compound No. 1-28), Example 40 (Compound No. 1-77), Example 44 (Compound No. 138) Example 45 (Compound No. 1 -1 3 9 ), Example 4 9 (Compound No. 1 5 6 ) 'Example 5 7 (Compound No. 1-194), Example 5S (Compound No. 195), and implementation Example 63 (Compound No. Code]-2 〇〇), Example 7 1 (Compound No. 1 - 2 1 3 ), Example 7 2 (Compound No. 2 1 4 ), Example 8 1 (Compound No. 1 - 2 3 5 ), and implementation Example 8 5 (Compound No. 2 3 9 ), Example 8 9 (Compound No. 1 - 2 4 4 ), Example 9 0 (Chemical-78- Amendment Page 1314041 g) 匕 吵 年 c4#

Compound No. 1-246), the onset of the disease, Sun H, Test Example 2 - Tomato gray mold control test (preventive effect) In the potted cultivation test plants (tomato: large Fushou) at the 2nd to 3rd leaf stage, The precursor was dissolved in dimethyl hydrazine and methanol (volume ratio: 7:3), and a dispersion liquid containing 300 ppm of the compound of the present invention was uniformly dispersed. One day after the cultivation, the pathogen suspension in the pot was spray-inoculated, and the pot was placed in an inoculation room at room temperature of 20 to 23 degrees to promote the onset. The incidence of the disease 2 days after the inoculation was investigated. The test was carried out in 2 rows. In addition, the degree of the disease was visually observed by the naked eye, and it was judged by the following criteria, and it was represented by the 4th order of 0 to 3. The degree of disease i 〇 % : There is no disease at all. 1 : The incidence is less than 40% of the untreated area. 2: The incidence is 40% or more and less than 80%. 3: The incidence is more than 80%. Results of the test, Example U compound number 1-11), Example 2 (Compound No. 1-17), Example 3 (Compound No. I-52), Example 4 (Compound No. 1-1), Examples 5 (Compound No. 1-12), Example 7 (Compound No. 1-14), Example 8 (Compound No. 1-15), Example 9 (Compound No. 1-16), and Example 10 (Compound No. 1 - 30), Example 11 (Compound No. 1-32), Example 14 (Compound No. 1-44), Example 17 (Compound No. 1-67), Example 18 (Compound No. 1-71), Example 19 (Compound No. 1-73), Example 20 (Compound No. 1-74), Example 22 (Compound No. 1-123), Example 24 (Compound No. 1-13 5), and Example 2 7 (Compound No. 1) -1 9 ), Example 2 8 (Compound No. 1 - 2 0 ), Example-79- Amendment Page 1314041 Mao Qi ι〇3 0 (Compound No. 28), Example 36 (Compound No. 1_5), Examples 3 9 (Compound No. 75), Example 4 (Compound No. 77), Example 41 (Compound No. 1-78), Example 45 (Compound No. I·139), and Example 46 (Compound No. 丨) ·146), Example 49 (Compound No. 1_156), Example 62 (Compound No. 1-199), Example 63 (Compound No. 1-200), Example 67 (Compound No. 1-208), Example 6 8 (Compound No. 1) -210), Example 71 (Compound No. 1-213), Example 72 (Compound No. 1-214), Example 73 (Compound No. 21 9), Example 74 (Compound No. 1-220), and Examples 75 (Compound No. 221), Example 76 (Compound No. 1_222), Example 81 (Compound No. 23 · 23 5), Example 87 (Compound No. 1-241), and Example 91 (Compound No. I-247) <) The compound of Example 92 (Compound No. 1 - 248) has an onset degree of industrially available wood. The compound of the invention is used as a fungicide for agricultural and horticultural use on the host plant, because Plant pathogenic bacteria, particularly for rice blast, have excellent effects and are excellent as agricultural and horticultural fungicides. The compound of the present invention exerts excellent effects on plant diseases, and examples thereof include, for example, Pyricularia oryzae, and cucumber, cockroach, and ugly mold (Botrytis cinerea). The bactericidal spectrum of the compound of the present invention is not particularly limited. [Simple description of the map]: None -80-

Claims (1)

131404^ ;· 修正 Amendment to this patent No. 92 1 29002 "Quinoline_3_Carboxyamine Compound" (amended on April 1, 2009) ' Pickup, Patent Range: Θ ι · Species (I a compound or a salt thereof, Wherein: Α is a c3~Ci 院 ring group which may be substituted by 1~4 Ci~C6 alkyl groups which are the same or different, and R series means selected from the group consisting of _ 素 atoms, ^ 〜 (^ alkoxy groups and a group of 1 to 3 substituents substituted with the same or different 1 to 3 substituents in the group of phenoxy groups, which may be selected from the group consisting of a dentate atom, a Cl~c6 alkoxy group, a phenyl group, and a phenoxy group. a c2 to C6 alkenyl group substituted with the same or different 1 to 3 substituents, and the same or different 1 to 3 substituents selected from the group consisting of a halogen atom, a Cl~C6 alkoxy group, and a phenoxy group The substituted c2~c6 alkynyl group may be selected from a halogen atom, a K6 group substituted with the same or different 1 to 3 halogen atoms, (^~(:6 alkoxy group, which may be the same or different 1~2) An aryl Cl~c6 alkyl group substituted with the same or different 1 to 6 substituents in the group of amine, nitro, cyano, or hydroxy groups substituted by a group, or may be selected from C^C:6 a heteroaryl C丨~c6 alkyl group substituted with the same or different 1 to 6 substituents in the alkyl group, X is represented by an oxygen atom or a sulfur atom, and γ is represented by a halogen atom, Substituting the same or different 1 to 3 halogen atoms, the same or different 1 to 3 halogen atoms 1314041, the substituted Ci-C: 6 alkoxy group, which may be the same or different 1~2 (^~(^6) The substituent in the group of the amine group, the nitro group, the thiol group, the chlorothio group and the Cl~c6 alkylthio group, and the η system represents an integer of 0 to 5. The compound of claim 1 or a salt thereof, wherein the octasystem is a C3~C1Q cycloalkyl group which may be substituted with 1 to 4 methyl groups. 3 · The compound of the first aspect of the patent application or a salt thereof, wherein the human system Is a cyclopentyl group, a cyclohexyl group or a cycloheptyl group. 4. A compound according to claim 1 or a salt thereof, wherein the octasystem is a cyclohexyl group. [5], as claimed in claim 1 to 4 A compound or a salt thereof, preferably wherein R is substituted with the same or different 1-6 substituents selected from the group consisting of a halogen atom, a Ci-C6 alkyl group, a Ci~C6oxy group, and a hydroxyl group. The compound of any one of the items 1 to 4, or a salt thereof, wherein the R system is selected from the group consisting of acne protoplasts. a benzyl group substituted with the same or different 1 to 6 substituents in the group of Ci~C6, the oxy group and the hydroxy group. 7_ The compound of any one of claims 1 to 4 Or a salt thereof, wherein R is a benzyl group. The compound or a salt thereof according to any one of claims 1 to 4, wherein X is an oxygen atom. The compound or a salt thereof, wherein Y is a fluorine atom, a hydroxyl group or a methyl group, and η is hydrazine or 1. The compound or a salt thereof according to any one of claims 1 to 4, wherein修正 Revised 1314041 for methyl and η for 0 or 1. The compound of claim 1 or a salt thereof, which comprises Ν-(1-benzylcyclohexyl)salostium-3-carboxamide, Ν·(ι_benzylmethylcyclohexyl) Quinoline_3-hydroxythiazamide, N-[l-(3-fluorobenzyl)cyclohexyl]quinoline-3-carboxycarbamide, N-[l-(4-fluorobenzyl) ring Hexyl]porphyrin·3-carboxamide, Ν-(1·benzylcyclohexyl)-8-methylsalvin-3-carboxamide, N-(l-benzylcyclohexyl)-8 Fluoroquinoline-3-carboxamide, N-(l-benzylcyclohexyl)-8-fluoroquinoline-3-hydroxythioguanamine, N-(l-benzylcycloheptyl)quinoline-3 - decylamine, N-[l-(3,4-difluorobenzyl)cyclohexyl]quinoline-3-carboxylamine, or N-[l-(3,5-difluorobenzyl) Cyclohexyl]chun «quinoline-3-carboxyguanamine or its salt. A bactericidal active pesticide which comprises, as an active ingredient, a compound or a salt thereof according to any one of claims 1 to j.