WO2011049150A1 - Pyrone compound and its use for pest control - Google Patents

Pyrone compound and its use for pest control Download PDF

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Publication number
WO2011049150A1
WO2011049150A1 PCT/JP2010/068538 JP2010068538W WO2011049150A1 WO 2011049150 A1 WO2011049150 A1 WO 2011049150A1 JP 2010068538 W JP2010068538 W JP 2010068538W WO 2011049150 A1 WO2011049150 A1 WO 2011049150A1
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group
optionally substituted
member selected
hydrogen atom
membered heterocyclic
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PCT/JP2010/068538
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French (fr)
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Sadayuki Arimori
Akira Shuto
Hajime Mizuno
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Sumitomo Chemical Company, Limited
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Publication of WO2011049150A1 publication Critical patent/WO2011049150A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/86—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings

Definitions

  • the present invention relates to a pyrone compound and its use for pest control.
  • the present invention has an object of providing a novel compound having an excellent controlling effect on pests .
  • a pyrone compound represented by following formula (1) has an excellent controlling effect on pests, leading to completion of the present invention.
  • the present invention relates to the following inventions.
  • Q 1 represents an oxygen atom or sulfur atom
  • n 0 or 1
  • R 1 , R 2 , R 3 and R 4 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, C3-C6
  • alicyclic hydrocarbon group optionally substituted by at least one halogen atom, phenyl group optionally
  • L 1 represents an oxygen atom, -S(0)m- or - NR 11 -,
  • n 0, 1 or 2
  • R 9 represents a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, phenyl group optionally substituted by at least one member selected from Group X, 5-membered heterocyclic group optionally substituted by at least one member selected from Group X, 6-membered heterocyclic group optionally substituted by at least one member selected from Group X or hydrogen atom (with the proviso that R 9 does not represent a hydrogen atom when L 1 is -S(0)m- and m is 1 or 2 ) ,
  • R 10 represents a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, Cl- C6 alkoxy group optionally substituted by at least one halogen atom, C1-C6 alkylamino group optionally
  • dialkylamino group optionally substituted by at least one halogen atom, hydrogen atom, hydroxy group or amino group,
  • R 11 represents a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, or hydrogen atom.
  • R 5 and R 6 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, C3-C6 alicyclic hydrocarbon group optionally substituted by at least one halogen atom, phenyl group optionally substituted by at least one member selected from Group X, 5-membered
  • heterocyclic group optionally substituted by at least one member selected from Group X, 6-membered
  • L 2 represents an oxygen atom, -S(0)m- or - NR 13 - (m and R 10 represent the same meaning as described above)
  • R 12 and R 13 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted by at least one member selected from Group W, C3-C6 alicyclic hydrocarbon group optionally substituted by at least one member selected from Group a, phenyl group optionally substituted by at least one member selected from Group X, 5-membered heterocyclic group optionally substituted by at least one member selected from Group X, 6-membered heterocyclic group optionally substituted by at least one member selected from Group X, or
  • R 12 and R 13 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected.
  • R 7 and R 8 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted by at least one member selected from Group W, hydrogen atom, or -L 3 R 14 , alternatively, R 7 and R 8 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected;
  • Q 3 represents an oxygen atom or sulfur atom
  • R 14 represents a C1-C6 chain hydrocarbon group optionally substituted by at least one member selected from Group W, C3-C6 alicyclic hydrocarbon group
  • heterocyclic group optionally substituted by at least one member selected from Group X, hydrogen atom or - L 4 R 15 (with the proviso that R 14 does not represent a hydrogen atom when L 3 is -S(0) 2 -; and except that -NR 7 R 8 is -NHCOC 6 H 5 ) ,
  • L 4 represents an oxygen atom or -NR 16 -
  • R 15 and R 16 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted by at least one member selected from Group , C3-C6 alicyclic hydrocarbon group optionally substituted by at least one member selected from Group a, phenyl group optionally substituted by at least one member selected from Group X, 5-membered heterocyclic group optionally substituted by at least one member selected from Group X, 6-membered heterocyclic group optionally substituted by at least one member selected from Group X, or
  • R 15 and R 16 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected;
  • Group X the group consisting of C1-C4 alkyl groups optionally substituted by at least one halogen atom, Cl- C4 alkoxy groups optionally substituted by at least one halogen atom, cyano group, nitro group and halogen atoms ;
  • Group Y the group consisting of C1-C4 alkoxy groups optionally substituted by at least one halogen atom, Cl- C4 alkylthio groups optionally substituted by at least one halogen atom, benzyloxy group optionally substituted by at least one halogen atom, C2-C6 alkoxy groups optionally substituted by at least one halogen atom, cyano group and halogen atoms;
  • Group a the group consisting of C1-C3 alkyl groups, C1-C4 alkoxy groups optionally substituted by at least one halogen atom, C1-C4 alkylthio groups optionally substituted by at least one halogen atom, cyano group and halogen atoms;
  • Group the group consisting of C1-C4 alkoxy groups optionally substituted by at least one halogen atom, Cl- C4 alkylthio groups optionally substituted by at least one halogen atom, benzyloxy group optionally substituted by at least one halogen atom, C2-C6 alkoxy groups optionally substituted by at least one halogen atom, cyano group, halogen atoms, C3-C6 alicyclic hydrocarbon groups optionally substituted by at least one member selected from Group a, phenyl groups optionally
  • inventive compound (hereinafter, referred to as the inventive compound) .
  • R 7 and R 8 may be bound to form a 5-membered heterocyclic ring
  • R 15 is a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group W, C3-C6 alicyclic hydrocarbon group optionally
  • R 16 is a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, or hydrogen atom, alternatively, R 15 and R 16 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected
  • Group Z the group consisting of C3-C6 alicyclic hydrocarbon groups optionally substituted by at least one member selected from Group a, phenyl groups
  • R 7 and R 8 may be bound to form a 5-membered heterocyclic ring
  • Q 3 is an oxygen atom
  • R 14 is a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, C3-C6 alicyclic hydrocarbon group optionally
  • R 15 is a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group W or C3-C6 alicyclic hydrocarbon group optionally
  • R 16 is a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y or hydrogen atom (here, L 3 and L 4 are the same meaning as defined in [1] .), in formula (1) .
  • Q 3 is an oxygen atom
  • R 14 is a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, cyclopropyl group optionally substituted by at least one member selected from Group a or -L R 15 ,
  • R 15 is a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group W or cyclopropyl group optionally substituted by at least one member selected from Group a,
  • R 16 is a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y or hydrogen atom (here, L 3 and L 4 are the same meaning as defined in [1] .) , in formula (1) .
  • a pest control agent comprising the pyrone compound as described in any one of [1] to [12] and an inert carrier.
  • a pest control method comprising applying an effective amount of the pyrone compound as described in any one of [1] to [12] to pests or areas where pests live .
  • the inventive compound Since the inventive compound has a controlling activity on pests, the compound is useful as an active ingredient of a pest control agent.
  • halogen atom means a fluorine atom, chlorine atom, bromine atom or iodine atom
  • heterocyclic group means a mono-valent group having a structure obtained by removing one hydrogen atom existing on a ring of a heterocyclic compound
  • hydrocarbon group means a mono-valent group having a structure obtained by removing one hydrogen atom existing on a hydrocarbon compound.
  • C3-C6 in “C3-C6 alicyclic hydrocarbon group” means that the number of carbon atoms constituting a ring of an alicyclic hydrocarbon group is in the range of 3 to 6.
  • optionally substituted by at least one halogen atom include C1-C6 alkyl groups optionally substituted by at least one halogen atom such as a methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, 1-methylbutyl group, 2-methylbutyl group, isopentyl group, tert-pentyl group, neopentyl group, hexyl group, isohexyl group, fluoromethyl group,
  • difluoromethyl group trifluoromethyl group, 2,2,2- trifluoroethyl group, pentafluoroethyl group,
  • C2-C6 alkenyl groups optionally substituted by at least one halogen atom such as an ethenyl group, 1- propenyl group, 2-propenyl group, 1-butenyl group, 2- butenyl group, 3-butenyl group, 1-methylethenyl group, 1-methylpropenyl group, 1 , 2-dimethylpropenyl group, 2- methyl-2-propenyl group, 3-methyl-2-butenyl group, 2,3- dimethyl-2-butenyl group, 2-pentenyl group, 2-hexenyl group, 2 , 2-difluoroethenyl group, 2 , 2 -dichloroethenyl group and 3 , 3 , 3-trifluoro-l-propenyl group and the like;
  • halogen atom such as an ethenyl group, 1- propenyl group, 2-propenyl group, 1-butenyl group, 2- butenyl group, 3-butenyl
  • C2-C6 alkynyl groups optionally substituted by at least one halogen atom such as an ethynyl group, 1- propynyl group, 2-propynyl group, 1-butynyl group, 2- butynyl group, 3-butynyl group, 3 , 3 , 3-trifluoro-1- propynyl group and 3 , 3 , 3-trichloro- 1-propynyl group and the like.
  • halogen atom such as an ethynyl group, 1- propynyl group, 2-propynyl group, 1-butynyl group, 2- butynyl group, 3-butynyl group, 3 , 3 , 3-trifluoro-1- propynyl group and 3 , 3 , 3-trichloro- 1-propynyl group and the like.
  • C3-C6 alicyclic hydrocarbon group optionally substituted by at least one halogen atom examples include a cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 2,2- difluorocyclopropyl group, 2,2,3,3- tetrafluorocyclopropyl group, 2 , 2-dichlorocyclopropyl group and 2 , 2 , 3 , 3-tetrachlorocyclopropyl group.
  • phenyl group optionally substituted by at least one member selected from Group X examples include a phenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4 -fluorophenyl group, 2-chlorophenyl group, 3- chlorophenyl group, 4 -chlorophenyl group, 2-methylphenyl group, 3-methylphenyl group, 4 -methylphenyl group, 2- methoxyphenyl group, 3-methoxyphenyl group, 4- methoxyphenyl group, 2 -( tri fluoromethyl ) phenyl group, 3- (trifluoromethyl ) phenyl group, 4 -( tri fluoromethyl ) phenyl group, 2- (trifluoromethoxy) phenyl group, 3- ( trifluoromethoxy) phenyl group, 4-
  • Group X optionally substituted by at least one member selected from Group X" include 5-membered saturated heterocyclic groups such as a pyrrolidin-l-yl group, tetrahydrofuran- 2-yl group, tetrahydrofuran-3-yl group, 2,2- difluorotetrahydrofuran-5-yl group, 2,2- difluorotetrahydrofuran-3-yl group and 3,3- difluorotetrahydrofuran-4 -yl group and the like;
  • 5-membered aromatic heterocyclic groups such as a pyrazol-l-yl group, 3-methylpyrazol-l-yl group, 4- methylpyrazol-l-yl group, 5-methylpyrazol-l-yl group, 3- fluoropyrazol-l-yl group, 4-fluoropyrazol-l-yl group, 5- fluoropyrazol-l-yl group, 3-chloropyrazol-l-yl group, 4- chloropyrazol-l-yl group, 5-chloropyrazol-l-yl group, 3- cyanopyrazol-l-yl group, 4-cyanopyrazol-l-yl group, 5- cyanopyrazol-l-yl group, pyrrol-l-yl group, 2- methylpyrrol-l-yl group, 3-methylpyrrol-l-yl group, 2- fluoropyrrol-l-yl group, 3-fluoropyrrol-l-yl group, 2- chloropyrrol-l-yl
  • thiophen-2-yl group 3-methylthiophen-2-yl group, 4- methylthiophen-2-yl group, 5-methylthiophen-2 -yl group, 3-fluorothiophen-2-yl group, 4 -fluorothiophen-2-yl group, 5-fluorothiophen-2-yl group, 3-chlorothiophen-2- yl group, 4-chlorothiophen-2-yl group, 5-chlorothiophen- 2-yl group, 3-cyanothiophen-2 -yl group, 4 -cyanothiophen-
  • Group X optionally substituted by at least one member selected from Group X" include 6-membered saturated heterocyclic groups such as a piperidin-l-yl group, morpholyl group, thiomorpholyl group and 4-methylpiperazin-l-yl group and the like;
  • 6-membered aromatic heterocyclic groups such as a pyridin-2-yl group, 3-methylpyridin-2-yl group, 4- methylpyridin-2-yl group, 5-methylpyridin-2-yl group, 6- methylpyridin--2 -yl group, 3-fluoropyridin-2-yl group, 4- fluoropyridin-2-yl group, 5-fluoropyridin-2 -yl group, 6- fluoropyridin-2 -yl group, 3-chloropyridin-2-yl group, 4- chloropyridin-2 -yl group, 5-chloropyridin-2-yl group, 6- chloropyridin-2 -yl group, 3-cyanopyridin-2-yl group, 4- cyanopyridin-2-yl group, 5-cyanopyridin-2-yl group, 6- cyanopyridin-2-yl group, pyridin-3-yl group, 2- methylpyridin-3-yl group, 4 -methylpyr
  • substituted by at least one halogen atom include C1-C6 alkoxy groups optionally substituted by at least one halogen atom such as a methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, 1-methylbutoxy group, 2-methylbutoxy group, isopentyloxy group, tert-pentyloxy group, neopentyloxy group, hexyloxy group, isohexyloxy group, fluoromethoxy group, difluoromethoxy group, trifluoromethoxy group, 2 , 2 , 2-trifluoroethoxy group, pentafluoroethoxy group, chloromethoxy group, dichloromethoxy group,
  • C2-C6 alkenyloxy groups optionally substituted by at least one halogen atom such as an ethenyloxy group, 1- propenyloxy group, 2-propenyloxy group, 1-butenyloxy group, 2-butenyloxy group, 3-butenyloxy group, 1-methyl- 1-ethenyloxy group, 1-methyl-l-propenyloxy group, 1,2- dimethyl-l-propenyloxy group, 2-methyl-2-propenyloxy group, 3-methyl-2-butenyloxy group, 2 , 3-dimethyl-2- butenyloxy group, 2-pentenyloxy group, 2,2- difluoroethenyloxy group, 2 , 2 -dichloroethenyloxy group and 3, 3, 3-trifluoro-l-propenyloxy group and the like;
  • halogen atom such as an ethenyloxy group, 1- propenyloxy group, 2-propenyloxy group, 1-butenyloxy group,
  • C2-C6 alkynyloxy groups optionally substituted by at least one halogen atom such as an ethynyloxy group, 1- propynyloxy group, 2-propynyloxy group, 1-butynyloxy group, 2-butynyloxy group, 3-butynyloxy group, 3,3,3- trifluoropropynyloxy group and 3,3,3- trichloropropynyloxy group and the like.
  • halogen atom such as an ethynyloxy group, 1- propynyloxy group, 2-propynyloxy group, 1-butynyloxy group, 2-butynyloxy group, 3-butynyloxy group, 3,3,3- trifluoropropynyloxy group and 3,3,3- trichloropropynyloxy group and the like.
  • C1-C6 alkylamino group optionally substituted by at least one halogen atom examples include C1-C6 alkylamino groups optionally substituted by at least one halogen atom such as a methylamino group, ethylamino group, propylamino group, isopropylamino group,
  • butylamino group isobutylamino group, see-butylamino group, tert-butylamino group, pentylamino group, 1- methylbutylamino group, 2-methylbutylamino group, isopentylamino group, tert-pentylamino group,
  • neopentylamino group hexylamino group, isohexylamino group, 2 , 2 , 2-trifluoroethylamino group and 2,2,2- trichloroethylamino group and the like;
  • C3-C6 alkenylamino groups optionally substituted by at least one halogen atom such as a 2-propenylamino group, 2 -butenylamino group, 3-butenylamino group, 2- methyl-2-propenylamino group, 3-methyl-2-butenylamino group, 2 , 3-dimethyl-2 -butenylamino group, 2- pentenylamino group, 2-hexenylamino group and 3,3- difluoro2-propenylamino group and the like;
  • halogen atom such as a 2-propenylamino group, 2 -butenylamino group, 3-butenylamino group, 2- methyl-2-propenylamino group, 3-methyl-2-butenylamino group, 2 , 3-dimethyl-2 -butenylamino group, 2- pentenylamino group, 2-hexenylamino group and 3,3- difluoro2-propenylamin
  • C3-C6 alkynylamino groups optionally substituted by at least one halogen atom such as a 2 -propynylamino group, 2-butynylamino group and 3-butynylamino group and the like.
  • halogen atom such as a 2 -propynylamino group, 2-butynylamino group and 3-butynylamino group and the like.
  • Examples of "C2-C8 dial kylamino group optionally substituted by at least one halogen atom” include a dimethylamino group, diethylamino group, dipropylamino group, dibutylamino group and bis (2,2,2- trifluoroethyl) amino group.
  • Group " include a methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group,
  • 2-hexenyl group 1-fluoroethenyl group, 1,2- difluoroethenyl group, 2 , 2-difluoroethenyl group, 1,2,2 trifluoroethenyl group, 1-chloroethenyl group, 1,2- dichloroethenyl group, 2 , 2 -dichloroethenyl group, 1,2,2 trichloroethenyl group, 1, 2-difluoropropenyl group, 3 , 3 , 3-trifluoropropenyl group, ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, methoxymethyl group, 1- methoxyethyl group, 2-methoxyethyl group, 1- methoxypropyl group, 2-methoxypropyl group, 3- methoxypropyl group, 1-methoxybuty
  • chloromethoxymethyl group dichloromethoxymethyl group, trichloromethoxymethyl group, 2,2,2- trichloroethoxymethyl group, 2 -propenyloxymethyl group, 2-butenyloxymethyl group, 3-butenyloxymethyl group, 2- propynyloxymethyl group, methylthiomethyl group, 1- methylthioethyl group, 2-methylthioethyl group, 1- methylthiopropy1 group, 2 -methylthiopropyl group, 3- methylthiopropyl group, 1-methylthiobutyl group,
  • ethylthiomethyl group 1-ethylthioethyl group, 1- ethylthiopropyl group, 1-ethylthiobutyl group,
  • benzyloxymethyl group cyanomethyl group, 1-cyanoethyl group, 2-cyanoethyl group, 1-cyanopropyl group, 2- cyanopropyl group, 3-cyanopropyl group, 1-cyanobutyl group, 1-cyanopentyl group, 1-cyanohexyl group,
  • cyclopropylmethyl group 1-cyclopropylethyl group, 2- cyclopropylethyl group, 1-cyclopropylpropyl group, 2- cyclopropylpropyl group, 3-cyclopropylpropyl group, cyclobutylmethyl group, 1-cyclobutylethyl group, 2- cyclobutylethyl group, 2 , 2-difluorocyclopropylmethyl group, 1 , 2 , 2 , 3 , 3-pentafluorocyclopropylmethyl group, 2 , 2-dichlorocyclopropylmethyl group, 1,2,2,3,3- pentachlorocyclopropylmethyl group, phenylmethyl group,
  • Examples of the 5-membered heterocyclic ring or 6- membered heterocyclic ring in "R 7 and R 8 may be bound to form a 5-membered heterocyclic ring optionally
  • C3-C6 alicyclic hydrocarbon group optionally substituted by at least one member selected from Group a include a cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group,
  • methylcyclopropyl group 2-methylcyclopropyl group, 2,2 dimethylcyclopropyl group, 2 , 2 , 3-trimethylcyclopropyl group, 2 , 2 , 3 , 3-tetramethylcyclopropyl group, 1,2,2,3,3- pentamethylcyclopropyl group, 1-fluorocyclopropyl group 2-fluorocyclopropyl group, 2 , 2-difluorocyclopropyl group, 2 , 2 , 3-trifluorocyclopropyl group, 2,2,3,3- tetrafluorocyclopropyl group, 2 , 2-dichlorocyclopropyl group, 2 , 2 , 3 , 3-tetrachlorocyclopropyl group,
  • C1-C3 alkyl group examples include a methyl group, ethyl group and propyl group.
  • substituted by at least one halogen atom include a methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, fluoromethyl group, difluoromethyl group, trifluoromethyl group, 2 , 2 , 2-trifluoroethyl group, pentafluoroethyl group, chloromethyl group, dichloromethyl group, trichloromethyl group and 2,2,2- trichloroethyl group.
  • substituted by at least one halogen atom include a methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, fluoromethoxy group, difluoromethoxy group, trifluoromethoxy group, 2 , 2 , 2-trifluoroethoxy group, pentafluoroethoxy group, chloromethoxy group, trichloromethoxy group and 2 , 2 , 2 -trichloroethoxy group.
  • C1-C4 alkylthio group optionally substituted by at least one halogen atom examples include a methylthio group, ethylthio group, propylthio group, isopropylthio group, butylthio group and 2,2,2- trifluoroethylthio group.
  • Benzyloxy group optionally substituted by at least one halogen atom includes a benzyloxy group, 2- chlorophenylmethoxy group, 3-chlorophenylmethoxy group and 4 -chlorophenylmethoxy group.
  • the present invention also relates to the following inventions .
  • Q 1 represents an oxygen atom or sulfur atom
  • n 0 or 1
  • R 1 , R 2 , R 3 and R 4 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, C3-C6
  • alicyclic hydrocarbon group optionally substituted by at least one halogen atom, phenyl group optionally
  • L 1 represents an oxygen atom, -S(0)m- or - NR 11 -,
  • n 0, 1 or 2
  • R 9 represents a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, phenyl group optionally substituted by at least one member selected from Group X, 5-membered heterocyclic group optionally substituted by at least one member selected from Group X, 6-membered heterocyclic group optionally substituted by at least one member selected from Group X or hydrogen atom (with the proviso that R 9 does not represent a hydrogen atom when L 1 is -S(0)m- and m is 1 or 2 ) ,
  • R 10 represents a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, Cl- C6 alkoxy group optionally substituted by at least one halogen atom, C1-C6 alkylamino group optionally
  • dialkylamino group optionally substituted by at least one halogen atom, hydrogen atom, hydroxy group or amino group,
  • R 11 represents a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, or hydrogen atom.
  • R 5 and R 6 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, C3-C6 alicyclic hydrocarbon group optionally substituted by at least one halogen atom, phenyl group optionally substituted by at least one member selected from Group X, 5-membered
  • heterocyclic group optionally substituted by at least one member selected from Group X, 6-membered
  • L 2 represents an oxygen atom, -S(0)m- or - NR 13 - (m and R 10 represent the same meaning as described above) ,
  • R 12 and R 13 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted by at least one member selected from Group W, C3-C6 alicyclic hydrocarbon group optionally substituted by at least one member selected from Group a, phenyl group optionally substituted by at least one member selected from Group X, 5-membered heterocyclic group optionally substituted by at least one member selected from Group X, 6-membered heterocyclic group optionally substituted by at least one member selected from Group X, or
  • R 12 and R 13 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected.
  • R 7 and R 8 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted by at least one member selected from Group W, hydrogen atom, or -L 3 R 14 , alternatively, R 7 and R 8 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected;
  • Q 3 represents an oxygen atom or sulfur atom
  • R 14 represents a C1-C6 chain hydrocarbon group optionally substituted by at least one member selected from Group W, C3-C6 alicyclic hydrocarbon group
  • heterocyclic group optionally substituted by at least one member selected from Group X, hydrogen atom or - L R 15 (with the proviso that R 1 does not represent a hydrogen atom when L 3 is -S(0) 2 -; and except that -NR 7 R 8 is -NHCOC 6 H 5 ) ,
  • L 4 represents an oxygen atom or -NR 16 -
  • R 15 and R 16 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted by at least one member selected from Group , C3-C6 alicyclic hydrocarbon group optionally substituted by at least one member selected from Group a, phenyl group optionally substituted by at least one member selected from Group X, 5-membered heterocyclic group optionally substituted by at least one member selected from Group X, 6-membered heterocyclic group optionally substituted by at least one member selected from Group X, or
  • R 15 and R 16 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected;
  • Group X the group consisting of C1-C4 alkyl groups optionally substituted by at least one halogen atom, Cl- C4 alkoxy groups optionally substituted by at least one halogen atom, cyano group, nitro group and halogen atoms ;
  • Group Y the group consisting of C1-C4 alkoxy groups optionally substituted by at least one halogen atom, Cl- C4 alkylthio groups optionally substituted by at least one halogen atom, benzyloxy group optionally substituted by at least one halogen atom, cyano group and halogen atoms ;
  • Group a the group consisting of C1-C3 alkyl groups, C1-C4 alkoxy groups optionally substituted by at least one halogen atom, C1-C4 alkylthio groups optionally substituted by at least one halogen atom, cyano group and halogen atoms;
  • Group W the group consisting of C1-C4 alkoxy groups optionally substituted by at least one halogen atom, CI- C4 alkylthio groups optionally substituted by at least one halogen atom, benzyloxy group optionally substituted by at least one halogen atom, cyano group, halogen atoms, C3-C6 alicyclic hydrocarbon groups optionally substituted by at least one member selected from Group a, phenyl groups optionally substituted by at least one member selected from Group X, 5-membered heterocyclic groups optionally substituted by at least one member selected from Group X and 6-membered heterocyclic groups optionally substituted by at least one member selected from Group X.
  • inventive compound (hereinafter, referred to as the inventive compound) .
  • R 2 is a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, phenyl group optionally substituted by at least one member selected from Group X, hydrogen atom, halogen atom, nitro group, cyano group or -L 1 R 9 (here, L 1 and R 9 are the same meaning as defined in [1-2]), in formula (1) .
  • R 10 is the same meaning as defined in [1-2]), in formula
  • R 7 and R 8 are the same or different and are a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group , hydrogen atom or -L 3 R 14 , alternatively, R 7 and R 8 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected,
  • R 15 is a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group , C3-C6 alicyclic hydrocarbon group optionally
  • R 16 is a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, or hydrogen atom, alternatively, R 15 and R 16 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected
  • Group Z the group consisting of C3-C6 alicyclic hydrocarbon groups optionally substituted by at least one member selected from Group a, phenyl groups
  • R 7 and R 8 are the same or different and are a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, hydrogen atom or -L 3 R 14 , alternatively, R 7 and R 8 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected,
  • Q 3 is an oxygen atom
  • R 14 is a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, C3-C6 alicyclic hydrocarbon group optionally
  • R 15 is a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group W or C3-C6 alicyclic hydrocarbon group optionally
  • R 16 is a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y or hydrogen atom (here, L 3 and L 4 are the same meaning as defined in [1-2] . ) , in formula (1) .
  • Q 3 is an oxygen atom
  • R 1 is a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, cyclopropyl group optionally substituted by at least one member selected from Group a or -L 4 R 15 ,
  • R 15 is a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group W or cyclopropyl group optionally substituted by at least one member selected from Group a,
  • R 16 is a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y or hydrogen atom (here, L 3 and L 4 are the same meaning as defined in [1-2].)/ in formula (1).
  • a pest control agent comprising the pyrone compound as described in any one of [1-2] to [12-2] and an inert carrier.
  • a pest control method comprising applying an effective amount of the pyrone compound as described in any one of [1-2] to [12-2] to pests or areas where pests live.
  • Examples of embodiments of the present invention include the following pyrone compounds.
  • Q 1 represents an oxygen atom
  • R 1 represents a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, hydrogen atom, halogen atom, nitro group, cyano group or -L 1 R 9 ;
  • R 1 represents a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, hydrogen atom or halogen atom;
  • R 3 represents a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, hydrogen atom, halogen atom, nitro group, cyano group or -L 1 R 9 ;
  • R 3 represents a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, hydrogen atom or halogen atom;
  • R 4 represents a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, hydrogen atom, halogen atom, nitro group, cyano group or -L 1 R 9 ;
  • R 4 represents a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, hydrogen atom or halogen atom;
  • R 5 represents a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, hydrogen atom or halogen atom;
  • R 1 , R 3 and R 4 are the same or different and
  • R 1 , R 3 , R 4 and R 5 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, hydrogen atom or halogen atom;
  • R 1 , R 3 , R 4 and R 5 represent a hydrogen atom; pyrone compounds represented by formula (1) in which R 2 represents a C1-C6 chain hydrocarbon optionally substituted by at least one halogen atom, phenyl group optionally substituted by at least one member selected from Group X, hydrogen atom, halogen atom, nitro group, cyano group or -L 1 R 9 ;
  • R 2 represents a phenyl group optionally substituted by at least one member selected from Group X, hydrogen atom or halogen atom;
  • R 2 represents a hydrogen atom
  • R 2 represents a phenyl group optionally substituted by at least one member selected from Group X, hydrogen atom or halogen atom;
  • R 2 represents a hydrogen atom or halogen atom
  • R 2 represents a hydrogen atom
  • R 6 represents a hydrogen atom or halogen atom
  • R 12 and R 13 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, or hydrogen atom,
  • R 12 and R 13 may be bound to form a 5- membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected;
  • n 0,
  • R 12 and R 13 are the same or different and represent a C1-C4 chain hydrocarbon group optionally substituted by a hydrogen atom, cyclopropyl group, cyclopropylmethyl group or hydrogen atom;
  • R 6 represents a hydrogen atom, halogen atom or - L 2 R 12 ;
  • R 12 and R 13 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, or hydrogen atom,
  • R 12 and R 13 may be bound to form a 5- membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected;
  • R 6 represents a hydrogen atom, halogen atom or - L 2 R 12 , L 2 represents -NR 13 - or S(0)m-, m represents 0,
  • R 12 and R 13 are the same or different and represent a C1-C4 chain hydrocarbon group optionally substituted by at least one halogen atom, cyclopropyl group,
  • Q 1 represents an oxygen atom
  • R 6 represents a hydrogen atom or halogen atom
  • R 6 represents a hydrogen atom
  • R 1 , R 3 , R 4 and R 5 represent a hydrogen atom
  • R 2 represents a hydrogen atom or halogen atom
  • R 6 represents a hydrogen atom, halogen atom or - L 2 R 12
  • L 2 represents -NR 13 - or S(0)m-
  • m represents 0,
  • R 12 and R 13 are the same or different and represent a C1-C4 chain hydrocarbon group optionally substituted by at least one halogen atom, cyclopropyl group,
  • R 1 , R 2 , R 3 , R 4 and R 5 represent a hydrogen atom, R 6 represents a hydrogen atom or halogen atom;
  • R 1 , R , R 3 , R 4 , R 5 and R 6 represent a hydrogen atom
  • Q 3 represents an oxygen atom
  • heterocyclic group optionally substituted by at least one member selected from Group X or -L 4 R 15 ;
  • R 15 represents a C1-C4 chain hydrocarbon group
  • R 16 and R 15 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected;
  • R 14 represents a methyl group, ethyl group, propyl group, isopropyl group, trifluoromethyl group
  • R 15 represents a methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, benzyl group, trifluoroethyl group, cyclopropyl group, cyclopropylmethyl group, 2-propenyl group or 2-propynyl group,
  • R 16 represents a methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, benzyl group, trifluoroethyl group, cyclopropyl group, cyclopropylmethyl group, 2-propenyl group, 2-propynyl group or hydrogen atom; pyrone compounds represented by formula (1) in which R 7 and R 8 are the same or different and represent a Cl- C3 chain hydrocarbon group optionally substituted by at least one member selected from Group W, hydrogen atom or -L 3 R 14 , alternatively, R 7 and R 8 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected,
  • R 1 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group W, C3-C6 alicyclic hydrocarbon group
  • R 15 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group , C3-C6 alicyclic hydrocarbon group
  • heterocyclic group optionally substituted by at least one member selected from Group X,
  • R 16 represents a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, or hydrogen atom, alternatively, R 16 and R 15 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected;
  • R 7 and R 8 are the same or different and represent a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group W, hydrogen atom, or -L 3 R 1 , alternatively, R 7 and R 8 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected,
  • R 14 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group , C3-C6 alicyclic hydrocarbon group
  • R 15 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group W, C3-C6 alicyclic hydrocarbon group
  • R 16 represents a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, or hydrogen atom, alternatively, R 16 and R 15 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected;
  • Q 3 represents an oxygen atom
  • R 7 and R 8 are the same or different and represent a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group W, hydrogen atom or -L 3 R 14 , alternatively, R 7 and R 8 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected,
  • R 14 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group W, C3-C6 alicyclic hydrocarbon group
  • R 15 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group , C3-C6 alicyclic hydrocarbon group
  • R 16 represents a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, or hydrogen atom
  • R 16 and R 15 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected
  • R 14 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group W, C3-C6 alicyclic hydrocarbon group
  • R 15 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group W or C3-C6 alicyclic hydrocarbon group optionally substituted by at least one member selected from Group a,
  • R 16 represents a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y or hydrogen atom;
  • R 7 and R 8 are the same or different and represent a
  • R 7 and R 8 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected,
  • R 14 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group , C3-C6 alicyclic hydrocarbon group
  • R 15 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group W or C3-C6 alicyclic hydrocarbon group optionally substituted by at least one member selected from Group a,
  • R 16 represents a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y or hydrogen atom;
  • Q 3 represents an oxygen atom
  • R 7 and R 8 are the same or different and represent a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group , hydrogen atom or -L 3 R 1 , alternatively, R 7 and R 8 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected,
  • R 1 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group W, C3-C6 alicyclic hydrocarbon group
  • R 15 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group or C3-C6 alicyclic hydrocarbon group optionally substituted by at least one member selected from Group a,
  • R 16 represents a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y or hydrogen atom;
  • Q 3 represents an oxygen atom
  • R 7 and R 8 are the same or different and represent a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group W, hydrogen atom or -L 3 R 14 , alternatively, R 7 and R 8 may be bound to form a 5-meitibered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected,
  • R 14 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, C3-C6 alicyclic hydrocarbon group
  • R 1 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group W or C3-C6 alicyclic hydrocarbon group optionally substituted by at least one member selected from Group a,
  • R 16 represents a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y or hydrogen atom;
  • Q 3 represents an oxygen atom
  • R 7 and R 8 are the same or different and represent a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, hydrogen atom or -L 3 ⁇ ,
  • R 14 represents a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, cyclopropyl group optionally substituted by at least one member selected from Group a or -L 4 R 15 , R 15 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group W or cyclopropyl group optionally substituted by at least one member selected from Group a,
  • R 16 represents a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y or hydrogen atom; pyrone compounds represented by formula (1) in which Q 1 represents an oxygen atom,
  • Q 3 represents an oxygen atom
  • R 7 and R 8 are the same or different and represent a methyl group, ethyl group, methoxymethyl group,
  • R 14 represents a methyl group, ethyl group, propyl group, isopropyl group, trifluoromethyl group,
  • R 15 represents a methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, benzyl group, tri fluoroethyl group, cyclopropyl group, cyclopropylmethyl group, 2-propenyl group or 2-propynyl group ,
  • R 16 represents a methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, benzyl group, trifluoroethyl group, cyclopropyl group, cyclopropylmethyl group, 2-propenyl group, 2-propynyl group or hydrogen atom; pyrone compounds represented by formula (1) in which
  • Q 1 represents an oxygen atom
  • R 1 , R 3 , R 4 and R 5 represent a hydrogen atom
  • R 2 represents a hydrogen atom or halogen atom
  • R 6 represents a hydrogen atom, halogen atom or -
  • L 2 represents -NR 13 - or S(0)m-, m represents 0, R 12 and R 13 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, or hydrogen atom,
  • R 12 and R 13 may be bound to form a 5- membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6 ⁇ membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected,
  • R 7 and R 8 are the same or different and represent a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group W, hydrogen atom or -L 3 R 14 , alternatively, R 7 and R 8 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected,
  • R 14 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group W, C3-C6 alicyclic hydrocarbon group
  • R 15 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group W or C3-C6 alicyclic hydrocarbon group optionally substituted by at least one member selected from Group a,
  • R 16 represents a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y or hydrogen atom; pyrone compounds represented by formula (1) in which Q 1 represents an oxygen atom,
  • R 1 , R 3 , R 4 and R 5 represent a hydrogen atom
  • R 2 represents a hydrogen atom or halogen atom
  • R 6 represents a hydrogen atom, halogen atom or -
  • L 2 represents -NR 13 - or S(0)m-, m represents 0,
  • R 1 and R 1 are the same or different and represent a C1-C4 chain hydrocarbon group optionally substituted by a hydrogen atom, cyclopropyl group, cyclopropylmethyl group or hydrogen atom,
  • R 7 and R 8 are the same or different and represent a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, hydrogen atom or -L 3 R 1 ,
  • R 14 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, cyclopropyl group optionally substituted by at least one member selected from Group . or -L 4 R 15 , R 15 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, cyclopropylmethyl group or cyclopropyl group optionally substituted by at least one member selected from Group a,
  • R 16 represents a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y or hydrogen atom; pyrone compounds represented by formula (1) in which
  • Q 1 represents an oxygen atom
  • R 7 and R 8 are the same or different and represent a hydrogen atom
  • Q 3 represents an oxygen atom
  • R 1 , R 2 , R 3 , R 4 , R 5 and R 6 represent a hydrogen atom
  • R 7 and R 8 are the same or different and represent a methyl group, ethyl group, methoxymethyl group
  • R 1 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, cyclopropyl group optionally substituted by at least one member selected from Group a or -L 4 R 15 ,
  • R 15 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, cyclopropylmethyl group or cyclopropyl group optionally substituted by at least one member selected from Group a,
  • R 16 represents a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y or hydrogen atom; pyrone compounds represented by formula (1) in which Q 1 represents an oxygen atom,
  • Q 3 represents an oxygen atom
  • R 1 , R 2 , R 3 , R 4 , R 5 and R 6 represent a hydrogen atom
  • R 7 and R 8 are the same or different and represent a methyl group, ethyl group, methoxymethyl group
  • R 14 represents a methyl group, ethyl group, propyl group, isopropyl group, trifluoromethyl group,
  • R 15 represents a methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, benzyl group, trifluoroethyl group, cyclopropyl group, cyclopropylmethyl group, 2-propenyl group or 2-propynyl group,
  • R 16 represents a methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, benzyl group, trifluoroethyl group, cyclopropyl group, cyclopropylmethyl group, 2-propenyl group, 2-propynyl group or hydrogen atom; pyrone compounds represented by formula (1) in which represents an oxygen atom, R 7 and R 8 are the same or different and represent a hydrogen atom; pyrone compounds represented by formula (1) in which Q 1 represents an oxygen atom,
  • R 7 and R 8 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted by at least one member selected from Group Y; pyrone compounds represented by formula (1) in which Q 1 represents an oxygen atom,
  • R 14 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group Y or C3-C6 alicyclic hydrocarbon group optionally substituted by at least one member selected from Group Y; pyrone compounds represented by formula (1) in which Q 1 represents an oxygen atom,
  • R 7 and R 8 are the same or different and represent - S(0) 2 R 1 ; pyrone compounds represented by formula (1) in which Q 1 represents an oxygen atom,
  • Q 1 represents an oxygen atom
  • R 1 , R 2 , R 3 , R , R 5 and R 6 represent a hydrogen atom
  • R 7 and R 8 are the same or different and represent a hydrogen atom
  • Q 1 represents an oxygen atom
  • R 1 , R 2 , R 3 , R 4 , R 5 and R 6 represent a hydrogen atom
  • R 7 and R 8 are the same or different and represent a
  • Q 1 represents an oxygen atom
  • R 1 , R 2 , R 3 , R 4 , R 5 and R 6 represent a hydrogen atom
  • R 7 and R 8 are the same or different and represent -
  • R 14 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group Y or C3-C6 alicyclic hydrocarbon group optionally substituted by at least one member selected from Group Y; pyrone compounds represented by formula (1) in which
  • Q 1 represents an oxygen atom
  • R 1 , R 2 , R 3 , R 4 , R 5 and R 6 represent a hydrogen atom
  • R 7 and R 8 are the same or different and represent -
  • Q 1 represents an oxygen atom
  • R 1 , R 2 , R 3 , R , R 5 and R 6 represent a hydrogen atom
  • R 7 and R 8 are the same or different and represent -
  • Q 1 represents an oxygen atom
  • R 1 , R 2 , R 3 , R 4 , R 5 and R 6 represent a hydrogen atom
  • R 7 and R 8 are the same or different and represent -
  • Q 1 represents an oxygen atom
  • R 1 , R 2 , R 3 , R 4 , R 5 and R 6 represent a hydrogen atom
  • R 7 and R 8 are the same or different and represent -
  • R 15 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group Y,
  • R 16 represents a C1-C5 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, C3-C6 alicyclic hydrocarbon group
  • R 14 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group Y or cyclopropyl group optionally substituted by at least one member selected from Group Y,
  • R 15 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group Y,
  • R 16 represents a C1-C5 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, C3-C6 alicyclic hydrocarbon group
  • R 14 represents a C1-C3 chain hydrocarbon group or cyclopropyl group
  • R 15 represents a C1-C3 chain hydrocarbon group
  • R 16 represents a C1-C5 chain hydrocarbon group, cyclopropyl group or hydrogen atom
  • Q 1 represents an oxygen atom
  • R 1 , R 3 , R 4 and R 5 represent a hydrogen atom
  • R 2 represents a hydrogen atom or halogen atom
  • R 6 represents a hydrogen atom, halogen atom or -
  • L 2 represents -NR 13 - or S(0)m-, m represents 0,
  • R 12 and R 13 are the same or different and represent a C1-C4 chain hydrocarbon group optionally substituted by a hydrogen atom, cyclopropyl group, cyclopropylmethyl group or hydrogen atom,
  • R 14 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group Y or cyclopropyl group optionally substituted by at least one member selected from Group Y,
  • R 15 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group Y,
  • R 16 represents a C1-C5 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, C3-C6 alicyclic hydrocarbon group
  • Q 1 represents an oxygen atom
  • R 1 , R 3 , R 4 and R 5 represent a hydrogen atom
  • R 2 represents a hydrogen atom or halogen atom
  • R 6 represents a hydrogen atom, halogen atom or - L 2 R 12 ,
  • L 2 represents -NR 13 - or S(0)m-, m represents 0,
  • R 12 and R 13 are the same or different and represent a C1-C4 chain hydrocarbon group optionally substituted by a hydrogen atom, cyclopropyl group, cyclopropylmethyl group or hydrogen atom,
  • R 8 3 ⁇ 4C1-C3 chain hydrocarbon group optionally
  • R 1 represents a C1-C3 chain hydrocarbon group or cyclopropyl group
  • R 15 represents a C1-C3 chain hydrocarbon group
  • R 16 represents a C1-C5 chain hydrocarbon group, cyclopropyl group or hydrogen atom; pyrone compounds represented by formula (1) in which Q 1 represents an oxygen atom,
  • R 1 , R 2 , R 3 , R 4 , R 5 and R 6 represent a hydrogen atom
  • R 1 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group Y or cyclopropyl group optionally substituted by at least one member selected from Group Y,
  • R 15 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group Y,
  • R 16 represents a C1-C5 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, C3-C6 alicyclic hydrocarbon group
  • R 1 , R 2 , R 3 , R 4 , R 5 and R 6 represent a hydrogen atom
  • R 14 represents a C1-C3 chain hydrocarbon group or cyclopropyl group
  • R 15 represents a C1-C3 chain hydrocarbon group
  • R 16 represents a C1-C5 chain hydrocarbon group, cyclopropyl group or hydrogen atom
  • R 1 , R 2 , R 3 , R 4 , R 5 and R 6 represent a hydrogen atom
  • R 1 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group Y or cyclopropyl group optionally substituted by at least one member selected from Group Y,
  • R 15 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group Y,
  • R 16 represents a C1-C5 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, C3-C6 alicyclic hydrocarbon group
  • Q 1 represents an oxygen atom
  • R 1 , R 2 , R 3 , R 4 , R 5 and R 6 represent a hydrogen atom
  • R 14 represents a C1-C3 chain hydrocarbon group or cyclopropyl group
  • R 15 represents a C1-C3 chain hydrocarbon group
  • R 16 represents a C1-C5 chain hydrocarbon group, cyclopropyl group or hydrogen atom
  • the inventive compound can be produced, for example, by the following (Production Method 1) to (Production Method 17) .
  • R 8 represents a hydrogen atom can be produced by reacting a compound (2) and a
  • R 1 , R 2 , R 3 , R , R 5 , R 6 and R 14 represent the same meaning as described above.
  • acetic anhydride is usually used as a solvent, and a mixed solvent with other solvents may also be used.
  • Examples of the other solvents to be used in the reaction include ethers such as tetrahydrofuran
  • THF time division duplex
  • ethylene glycol dimethyl ether 1,4-dioxane and the like
  • aromatic hydrocarbons such as toluene, xylene and the like
  • halogenated hydrocarbons such as
  • chlorobenzene , dichlorobenzene and the like, fatty acids such as acetic acid and the like and mixtures thereof.
  • the compound (3) is used usually in a proportion of 1 to 3 mol with respect to 1 mol of the compound (2) .
  • the reaction temperature of the reaction is usually in the range of 50 to 200°C, and the reaction time thereof is usually in the range of 0.1 to 24 hours.
  • a compound (4-p) is obtained in some cases.
  • the compound (4-a) and / or (4-p) can be isolated by performing post treatment operations such as, for example, cooling of the reaction mixture to room temperature, addition of ethanol or the like if necessary, and filtration of the deposited precipitate, drying thereof and the like.
  • post treatment operations such as, for example, cooling of the reaction mixture to room temperature, addition of ethanol or the like if necessary, and filtration of the deposited precipitate, drying thereof and the like.
  • the isolated compound (4-a) and/or (4-p) can also be further purified by chromatography, re-crystallization and the like .
  • a compound (5) in which n represents 0, Q 1 represents an oxygen atom and R 7 and R 8 represent a hydrogen atom can be produced by reacting a compound (4-a-a) with a Lewis acid, then, treating this with a basic solution.
  • R 1 , R 2 , R 3 , R 4 , R 5 and R 6 represent the same meaning as described above.
  • the reaction is carried out usually in the presence of a solvent.
  • a solvent examples include THF, alcohols such as methanol, ethanol and the like, ethers such as ethylene glycol dimethyl ether, 1,4-dioxane and the like, toluene, aromatic hydrocarbons such as xylene and the like, halogenated hydrocarbons such as dichloromethane , chloroform, chlorobenzene , dichlorobenzene and the like and mixtures thereof.
  • reaction include boron halides such as boron
  • Examples of the basic solution to be used include aqueous solutions of alkali metal carbonates such as a sodium carbonate aqueous solution, sodium hydrogen carbonate aqueous solution, potassium carbonate aqueous solution, potassium hydrogen carbonate aqueous solution and the like.
  • the Lewis acid is used usually in a proportion of 1 to 10 mol and the base in the basic solution is used usually in a proportion of 1 to 20 mol with respect to 1 mol of the compound (4-a-a) .
  • the reaction temperature in the process of reacting the compound (4-a-a) with the Lewis acid is usually in the range of 10 to 100°C, and the reaction time thereof is in the range of 0.1 to 24 hours.
  • the reaction mixture After completion of the reaction of the compound (4- a-a) with the Lewis acid, the reaction mixture is cooled to room temperature, the deposited precipitate is filtrated, and the resultant precipitate can be used as it is in a process of treating with a basic solution.
  • the treatment temperature in the process of treating with a basic solution is usually in the range of 0 to 25°C, and the treatment time thereof is usually in the range of 0.1 to 2 hours.
  • the compound (5) After treatment with a basic solution, the compound (5) can be isolated by performing post treatments such as filtration of the deposited precipitate, drying thereof and the like. The isolated compound (5) can also be further purified by chromatography, re- crystallization and the like.
  • R 8 represents a hydrogen atom
  • a compound (5) an acid chloride represented by formula (6) (hereinafter, referred to as a compound (6)) or an acid anhydride represented by formula (7) (hereinafter, referred to as a compound (7)) in the presence of a base.
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 14 and L 3 represent the same meaning as described above.
  • reaction is carried out usually in the presence of a solvent, however, the reaction may also be carried out in the absence of a solvent.
  • solvent to be used in the reaction examples include THF, nitriles such as acetonitrile and the like, acid amides such as N , N-dimethylformamide (hereinafter, referred to as, DMF in some cases), N-methyl-2 - pyrrolidinone (hereinafter, referred to as, NMP in some cases) and the like, sulfoxides such as dimethyl
  • DMSO sulfoxide
  • ethers such as ethylene glycol dimethyl ether, 1,4-dioxane and the like
  • aromatic hydrocarbons such as toluene, xylene and the like
  • halogenated hydrocarbons such as dichloromethane , chloroform, chlorobenzene , dichlorobenzene and the like and mixtures thereof.
  • Examples of the base to be used in the reaction include alkali metal carbonates such as sodium
  • the compound (6) or compound (7) is used usually in a proportion of 1 to 10 mol and the base is used usually in a proportion of 1 to 10 mol with respect to 1 mol of the compound (5) .
  • the reaction temperature of the reaction is usually in the range of 0 to 100°C, and the reaction time thereof is in the range of 0.5 to 24 hours.
  • a compound (4) can be isolated by performing post treatment operations such as extraction of the reaction mixture with an organic solvent, drying of the organic layer, concentration thereof and the like.
  • the compound (4) can be isolated by performing operations such as distillation off of the solvent, addition of water, filtration of the precipitate, drying thereof and the like, after completion of the reaction, as other post treatment operations.
  • the isolated compound (4) can also be further purified by
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 15 and Q 3 represent the same meaning as described above.
  • the reaction may be carried out in the absence of a solvent, or may be carried out using a solvent.
  • solvent to be used in the reaction examples include THF, nitriles such as acetonitrile and the like, acid amides such as DMF, N P and the like, ethers such as ethylene glycol dimethyl ether, 1,4-dioxane and the like, aromatic hydrocarbons such as toluene, xylene and the like, halogenated hydrocarbons such as
  • the compound (8) is used usually in a proportion of 1 to 100 mol with respect to 1 mol of the compound (5) .
  • the reaction temperature of the reaction is usually in the range of 0 to 200°C, and the reaction time thereof is usually in the range of 0.5 to 24 hours.
  • the compound (4-a- b) can be isolated by performing operations such as cooling of the reaction mixture to room temperature, filtration of the deposited precipitate, drying thereof and the like.
  • the isolated compound (4-a-b) can also be further purified by chromatography, re-crystallization and the like.
  • a compound (9) in which n represents 0, Q 1 represents an oxygen atom, and R 7 and R 8 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected can be produced by reacting a compound (4-b) in the resence of a base.
  • L 4 x represents a methylene group optionally substituted by at least one member selected from Group Y or -L 4
  • a 4 represents a methylene group optionally substituted by at least one member selected from Group Y
  • p represents 2 or 3
  • E represents a leaving group such as a chlorine atom, bromine atom or iodine atom and the like.
  • the reaction is carried out usually in the presence of a solvent.
  • solvent to be used in the reaction examples include THF, nitriles such as acetonitrile and the like, acid amides such as D F, NMP and the like, sulfoxides such as DMSO and the like, ethers such as ethylene glycol dimethyl ether, 1,4-dioxane and the like,
  • aromatic hydrocarbons such as toluene, xylene and the like, halogenated hydrocarbons such as dichloromethane , chloroform, chlorobenzene , dichlorobenzene and the like and mixtures thereof.
  • Examples of the base to be used in the reaction include alkali metal hydrides such as sodium hydride, potassium hydride and the like, alkali metal alkoxides such as sodium tert-butoxide, potassium tert-butoxide and the like, etc.
  • the base is used usually in a proportion of 1 to 10 mol with respect to 1 mol of the compound (4-b) .
  • the reaction temperature of the reaction is usually in the range of 0 to 100°C, and the reaction time thereof is usually in the range of 0.1 to 24 hours.
  • the compound (9) can be isolated by performing post treatment operations such as extraction of the reaction mixture with an organic solvent, drying of the organic layer,
  • compound (9) can also be further purified by
  • R 7 and R 8 may be bound to form a 5-membered heterocyclic ring optionally
  • substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected can be produced by reacting a compound (4-c) in the presence of a base in an acid anhydride.
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , L 4X and A 4 represent the same meaning as described above, q represents 1 or 2.
  • reaction is carried out usually using, as a solvent, acid anhydrides such as acetic anhydride, propionic anhydride and the like, however, other
  • solvents may also be mixed.
  • Examples of the other solvents to be used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, 1,4-dioxane and the like, aromatic hydrocarbons such as toluene, xylene and the like, halogenated hydrocarbons such as dichloromethane, chloroform, chlorobenzene , dichlorobenzene and the like, esters such as ethyl acetate, butyl acetate and the like and mixtures thereof.
  • ethers such as THF, ethylene glycol dimethyl ether, 1,4-dioxane and the like
  • aromatic hydrocarbons such as toluene, xylene and the like
  • halogenated hydrocarbons such as dichloromethane, chloroform, chlorobenzene , dichlorobenzene and the like
  • esters such as ethyl acetate, butyl acetate and the like and mixtures thereof.
  • the base to be used in the reaction includes fatty acid alkali metal salts such as sodium acetate,
  • the base is used usually in a proportion of 0.01 to 2 mol with respect to 1 mol of the compound (4-c).
  • the reaction temperature of the reaction is usually in the range of 10 to 200°C, and the reaction time thereof is usually in the range of 0.5 to 24 hours.
  • the compound (10) can be isolated by performing post treatments such as distillation off of the solvent, neutralization of the reaction mixture with a basic aqueous solution such as a sodium carbonate aqueous solution and the like,
  • the isolated compound (10) can also be further purified by chromatography, re-crystallization and the like.
  • a compound (12) in which n represents 0, Q 1 represents an oxygen atom and R 7 represents -L 3 R 14 can be produced by reacting a compound (4) with a compound (11) in the presence of a base.
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 14 , L 3 and E represent the same meaning as described above.
  • the reaction is carried out usually in the presence of a solvent .
  • solvent to be used in the reaction examples include THF, nitriles such as acetonitrile and the like, acid amides such as DMF, NMP and the like, sulfoxides such as DMSO and the like, ethers such as ethylene glycol dimethyl ether, 1,4-dioxane and the like, aromatic hydrocarbons such as toluene, xylene and the like, halogenated hydrocarbons such as dichloromethane , chloroform, chlorobenzene , dichlorobenzene and the like and mixtures thereof.
  • Examples of the base to be used in the reaction include alkali metal hydrides such as sodium hydride, potassium hydride and the like, alkali metal alkoxides such as sodium tert-butoxide, potassium tert-butoxide and the like, etc.
  • the compound (11) is used usually in a proportion of
  • the base is used usually in a proportion of 1 to 10 mol with respect to 1 mol of the compound (4) .
  • the reaction temperature of the reaction is usually in the range of 0 to 100°C, and the reaction time thereof is usually in the range of 0.5 to 24 hours.
  • the compound (12) can be isolated by performing post treatment operations such as extraction of the reaction mixture with an organic solvent, drying of the organic layer,
  • the isolated compound (12) can also be further purified by
  • a compound (12-a) in which n represents 0, Q 1 represents an oxygen atom and R 7 and R 8 represent -S(0) 2 R 14 can be produced by
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 1 represent the same meaning as described above.
  • the reaction is carried out usually in the presence of a solvent.
  • solvent to be used in the reaction examples include THF, nitriles such as acetonitrile and the like, acid amides such as DMF, NMP and the like, sulfoxides such as DMSO and the like, ethers such as ethylene glycol dimethyl ether, 1,4-dioxane and the like,
  • aromatic hydrocarbons such as toluene, xylene and the like, halogenated hydrocarbons such as dichloromethane , chloroform, chlorobenzene , dichlorobenzene and the like and mixtures thereof.
  • Examples of the base to be used in the reaction include alkali metal carbonates such as sodium
  • the compound (13) is used usually in a proportion of 1 to 10 mol and the base is used usually in a proportion of 1 to 10 mol with respect to 1 mol of the compound (5) .
  • the reaction temperature of the reaction is usually in the range of 0 to 100°C, and the reaction time thereof is in the range of 0.1 to 24 hours.
  • the compound (12- a) can be isolated by performing post treatment
  • the isolated compound (12-a) can also be further purified by
  • R 7 and R 8 represent a hydrogen atom can be produced by reacting a compound (5-a) with a halogenation reagent.
  • the reaction is carried out usually in the presence of a solvent.
  • the solvent to be used in the reaction includes halogenated hydrocarbons such as dichloromethane , chloroform and the like, fatty acids such as acetic acid, propionic acid and the like and mixtures thereof.
  • the halogenation reagent to be used in the reaction includes chlorine, bromine, N-chlorosuccinimide
  • NBS N- bromosuccinimide
  • the halogenation reagent is used usually in a proportion of 1 to 10 mol with respect to 1 mol of the compound ( 5-a ) .
  • the reaction temperature of the reaction is usually in the range of 0 to 100°C, and the reaction time thereof is in the range of 0.1 to 24 hours.
  • a compound (5-b) can be isolated by performing post treatment operations such as neutralization of the reaction mixture with a basice solution such as, for example, a sodium carbonate aqueous solution and the like, extraction of the
  • reaction mixture with an organic solvent, drying of the organic layer, concentration thereof and the like.
  • the isolated compound (5-b) can also be further purified by chromatography, re-crystallization and the like.
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 ' b and R 14 represent the same meaning as described above.
  • reaction is usually carried out in the absence of a solvent, however, the reaction may also be carried out using a solvent.
  • solvent to be used in the reaction examples include THF, nitriles such as acetonitrile and the like, acid amides such as DMF, NMP and the like, sulfoxides such as DMSO and the like, ethers such as ethylene glycol dimethyl ether, 1,4-dioxane and the like,
  • aromatic hydrocarbons such as toluene, xylene and the like, halogenated hydrocarbons such as dichloromethane , chloroform, chlorobenzene, dichlorobenzene and the like and mixtures thereof.
  • Examples of the base to be used in the reaction include alkali metal carbonates such as sodium
  • the compound (16) is used usually in a proportion of 1 to 10 mol and the base is used usually in a proportion of 2 to 100 mol with respect to 1 mol of the compound (5-b) .
  • the reaction temperature of the reaction is usually in the range of 0 to 100°C, and the reaction time thereof is in the range of 0.1 to 24 hours.
  • the compound (12- b) can be isolated by performing post treatment
  • the isolated compound (12-b) can also be further purified by chromatography, re- crystallization and the like.
  • R 7 represents a hydrogen atom
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 " b , R 12 , R 13 and R 1 represent the same meaning as described above.
  • reaction is carried out usually using a solvent, however, the reaction may also be carried out in the absence of a solvent.
  • solvent to be used in the reaction examples include THF, alcohols such as methanol, ethanol and the like, nitriles such as acetonitrile and the like, acid amides such as DMF, N P and the like, ethers such as ethylene glycol dimethyl ether, 1,4-dioxane and the like, aromatic hydrocarbons such as toluene, xylene and the like, halogenated hydrocarbons such as
  • the compound (17) is used usually in a proportion of 1 to 10 mol with respect to 1 mol of the compound (12- b) .
  • the reaction temperature of the reaction is usually in the range of 0 to 100°C, and the reaction time thereof is in the range of 0.1 to 24 hours.
  • the compound (4-d) can be isolated by performing post treatment operations such as distillation off of the solvent, extraction of the reaction mixture with an organic solvent, drying of the organic layer, concentration thereof and the like.
  • the isolated compound (4-d) can also be further purified by chromatography, re-crystallization and the like.
  • R 7 represents a hydrogen atom
  • reaction is carried out usually using a solvent, however, the reaction may also be carried out in the absence of a solvent.
  • solvent to be used in the reaction examples include THF, alcohols such as methanol, ethanol and the like, nitriles such as acetonitrile and the like, acid amides such as DMF, NMP and the like, ethers such as ethylene glycol dimethyl ether, 1,4-dioxane and the like, aromatic hydrocarbons such as toluene, xylene and the like, halogenated hydrocarbons such as
  • Examples of the base to be used in the reaction include alkali metal hydrides such as sodium hydride, potassium hydride and the like, alkali metal carbonates such as sodium carbonate, potassium carbonate and the like, etc.
  • the compound (18) is reacted with an alkali metal hydride such as sodium hydride and the like to prepare an alkali metal salt thereof, then, it is used in the above-described
  • the compound (18) is used usually in a proportion of 1 to 10 mol and the base is used usually in a proportion of 1 to 10 mol with respect to 1 mol of the compound (12-b) .
  • the reaction temperature of the reaction is usually in the range of 0 to 100°C, and the reaction time thereof is in the range of 0.1 to 24 hours.
  • the compound (4-e) can be isolated by performing post treatment operations such as distillation off of the solvent, extraction of the reaction mixture with an organic solvent, drying of the organic layer, concentration thereof and the like.
  • the isolated compound (4-e) can also be further purified by chromatography, re-crystallization and the like.
  • a compound (19) in which n represents 0, Q 1 represents an oxygen atom and R 7 represents a hydrogen atom can be produced by reacting a compound (12-c) in the presence of a Lewis acid, then, treating this with a basic solution.
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 8 represent the same meaning as described above.
  • the reaction is carried out usually in the presence of a solvent.
  • solvent to be used in the reaction examples include THF, alcohols such as methanol, ethanol and the like, ethers such as ethylene glycol dimethyl ether, 1,4-dioxane and the like, aromatic hydrocarbons such as toluene, xylene and the like, halogenated hydrocarbons such as dichloromethane , chloroform, chlorobenzene , dichlorobenzene and the like and mixtures thereof.
  • reaction include boron halides such as boron
  • Examples of the basic solution to be used include aqueous solutions of alkali metal carbonates such as a sodium carbonate aqueous solution, sodium hydrogen carbonate aqueous solution, potassium carbonate aqueous solution, potassium hydrogen carbonate aqueous solution and the like.
  • the Lewis acid is used usually in a proportion of 1 to 10 mol
  • the base in the basic solution is used usually in a proportion of 1 to 20 mol with respect to 1 mol of the compound (12-c) .
  • the reaction temperature in the process of reacting the compound (12-c) with the Lewis acid is usually in the range of 10 to 100°C, and the reaction time thereof is in the range of 0.5 to 24 hours.
  • the reaction mixture After completion of the reaction of the compound (12-c) with the Lewis acid, the reaction mixture is cooled to room temperature, the solvent is distilled, and the resultant residue can be used as it is in the process of treating with a basic solution.
  • the treatment temperature in the process of treating with a basic solution is usually in the range of 0 to 25°C, and the treatment time thereof is usually in the range of 0.1 to 2 hours.
  • the compound (19) can be isolated by performing post treatment operations such as, for example, distillation off of the solvent, extraction of the reaction mixture with an organic solvent, drying of the organic layer,
  • the isolated compound (19) can also be further purified by
  • a compound (1-b) in which n represents 1 and Q 1 represents an oxygen atom can be produced by reacting a compound (1-a) in the presence of an oxidizer.
  • R 1 , R 2 , R 3 , R , R 5 , R 6 , R 7 and R 8 represent the same meaning as described above.
  • the reaction is carried out usually in the presence of a solvent.
  • solvent to be used in the reaction examples include aliphatic halogenated hydrocarbons such as dichloromethane , chloroform and the like, acetic acid, water and mixtures thereof.
  • oxidizer to be used in the reaction examples include carboxylic acid peroxides such as 3- chloroperbenzoic acid and the like, and hydrogen
  • the oxidizer is used usually in a proportion of 1 to
  • the reaction temperature of the reaction is usually in the range of -20 to 100°C, and the reaction time thereof is usually in the range of 0.1 to 24 hours.
  • the compound (1-b) can be isolated by performing post treatment operations such as extraction of the reaction mixture with an organic solvent, washing of the organic layer with an aqueous solution of a reducing agent (for example, sodium sulfite, sodium thiosulfate) and an aqueous solution of a base (for example, sodium hydrogen
  • the isolated compound (1-b) can also be further purified by chromatography, re- crystallization and the like.
  • a compound (4-m) in which n represents 0 and Q 1 represents an oxygen atom can be produced by reacting a compound (4-n), an amine compound represented by formula (4-g) (hereinafter, referred to as a compound (4-g)) and a base.
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 15 and R 16 represent the same meaning as described above, and R ,1 J 5 - a represents a phenyl group optionally substituted by at least one member selected from Group X.
  • the reaction is carried out usually in the presence of a solvent.
  • a solvent examples include THF, nitriles such as acetonitrile and the like, acid amides such as DMF, NMP and the like, sulfoxides such as DMSO and the like, ethers such as t-butyl methyl ether, ethylene glycol dimethyl ether, 1,4-dioxane and the like, aromatic hydrocarbons such as toluene, xylene and the like, halogenated hydrocarbons such as
  • the amine compound (4-g) is used usually in a proportion of 1 to 10 mol with respect to 1 mol of the compound (4-n) .
  • a base is used.
  • Examples of the base to be used include alkali metal carbonates such as sodium carbonate, potassium carbonate and the like, tertiary amines such as triethylamine , diisopropylethylamine and the like, nitrogen-containing aromatic hydrocarbons such as pyridine, 4- dimethylaminopyridine and the like, etc.
  • the base is used usually in a proportion of 1 to 10 mol with respect to 1 mol of the amine compound (4-g) .
  • the reaction temperature of the reaction is usually in the range of 0 to 100°C, and the reaction time thereof is in the range of 0.5 to 24 hours.
  • the compound (4-m) can be isolated by performing post treatment operations such as extraction of the reaction mixture with an organic solvent, drying of the organic layer, concentration thereof and the like.
  • the compound (4-m) can be isolated by performing operations such as addition of water,
  • the isolated compound (4-m) can also be further purified by chromatography, re- crystallization and the like.
  • R 1 , R 2 , R 3 , R 4 , R 5 and R 14 represent the same meaning as described above.
  • reaction is carried out usually using a solvent, however, the reaction may also be carried out in the absence of a solvent .
  • solvent to be used in the reaction examples include THF, alcohols such as methanol, ethanol and the like, nitriles such as acetonitrile and the like, acid amides such as DMF, N P and the like, ethers such as ethylene glycol dimethyl ether, 1,4-dioxane and the like, aromatic hydrocarbons such as toluene, xylene and the like, halogenated hydrocarbons such as
  • Examples of the amine compound to be used in the reaction include primary amines such as methylamine, ethylamine and the like, secondary amines such as dimethylamine, diethylamine and the like, etc.
  • the amine compound is used usually in a proportion of 1 to 10 mol with respect to 1 mol of the compound (12-d) .
  • the reaction temperature of the reaction is usually in the range of 0 to 100°C, and the reaction time thereof is in the range of 0.1 to 48 hours.
  • the compound (4-q) can be isolated by performing post treatment operations such as distillation off of the solvent, extraction of the reaction mixture with an organic solvent, drying of the organic layer, concentration thereof and the like.
  • the isolated compound (4-q) can also be further purified by chromatography, re-crystallization and the like.
  • a compound (12-d) in which n represents 0 and Q represents an oxygen atom can be produced by reacting a compound (12-e) with triphenylphosphine .
  • R 1 , R 2 , R 3 , R 4 , R 5 and R 14 represent the same meaning as described above.
  • the reaction is carried out usually in the presence of a solvent.
  • solvent to be used in the reaction examples include THF, nitriles such as acetonitrile and the like, acid amides such as D F, NMP and the like, sulfoxides such as DMSO and the like, ethers such as ethylene glycol dimethyl ether, 1,4-dioxane and the like, water and mixtures thereof.
  • Triphenylphosphine is used usually in a proportion of 1 to 10 mol with respect to 1 mol of the compound (12-e) .
  • the reaction temperature of the reaction is usually in the range of 0 to 100°C, and the reaction time thereof is in the range of 0.5 to 24 hours.
  • a compound (12-d) can be isolated by performing post treatment operations such as extraction of the reaction mixture with an organic solvent, drying of the organic layer, concentration thereof and the like.
  • the compound (12-d) can be isolated by performing operations such as distillation off of the solvent, addition of water, filtration of the
  • the isolated compound (12-d) can also be further purified by chromatography, re-crystallization and the like.
  • intermediate in the present invention can be produced, for example, by the following method.
  • a compound (2) can be produced by reacting a compound (Ml) with a compound (M2).
  • R 1 , R 2 , R 3 , R 4 , R 5 and R 6 represent the same meaning as described above.
  • reaction is carried out usually in the absence of a solvent, however, the reaction may also be carried out using a solvent.
  • solvent to be used in the reaction examples include ethers such as THF, ethylene glycol dimethyl ether, 1,4-dioxane and the like, aromatic hydrocarbons such as toluene, xylene and the like and mixtures thereof .
  • Examples of the compound (M2) to be used in the reaction include N, N-dimethylformamide dimethylacetal, N, N-dimethylacetamide dimethylacetal, N,N- dimethylformamide diethylacetal , N , -dimethylacetamide diethylacetal and the like.
  • the compound (M2) is used usually in a proportion of 1 to 10 mol with respect to 1 mol of the compound (Ml) .
  • the reaction temperature of the reaction is usually in the range of 0 to 200°C, and the reaction time thereof is usually in the range of 0.1 to 72 hours.
  • the compound (2) can be isolated by performing post treatments such as distillation off of the compound (M2) and the solvent, and the like.
  • the isolated compound (2) can also be further purified by chromatography, re-crystallization and the like.
  • a compound (3) can be produced by reacting a
  • R 1 represents the same meaning as described above .
  • the reaction is carried out usually in the presence of a solvent.
  • Examples of the solvent to be used in the reaction include water, THF, nitriles such as acetonitrile and the like, acid amides such as D F, N P and the like, sulfoxides such as DMSO and the like and mixtures thereof .
  • Examples of the base to be used in the reaction include alkali metal hydrides such as sodium hydride, potassium hydride and the like, alkali metal carbonates such as sodium carbonate, sodium hydrogen carbonate, potassium carbonate, potassium hydrogen carbonate and the like and mixtures thereof, and the like.
  • the compound (16) is used usually in a proportion of
  • the base is used usually in a proportion of 1 to 10 mol with respect to 1 mol of the compound (M3) .
  • the reaction temperature of the reaction is usually in the range of 0 to 100°C, and the reaction time thereof is in the range of 0.5 to 36 hours.
  • the compound (3) can be isolated by performing post treatment operations such as distillation off of the solvent, rendering the reaction mixture acidic using hydrochloric acid and the like, then, extraction with an organic solvent, drying of the organic layer, concentration thereof and the like.
  • the isolated compound (3) can also be further purified by re-crystallization and the like.
  • a compound (4-c) can be produced by reacting a compound (5) with an acid anhydride represented . by formula (M4) (hereinafter, referred to as a compound (M4) ) .
  • the reaction is carried out usually in the presence of a solvent.
  • solvent to be used in the reaction examples include aromatic hydrocarbons such as toluene, xylene and the like, halogenated hydrocarbons such as
  • chlorobenzene bromobenzene , dichlorobenzene and the like, and mixtures thereof, and the like.
  • the compound (M4) is used usually in a proportion of 1 to 5 mol with respect to 1 mol of the compound (5) .
  • the reaction temperature of the reaction is usually in the range of 50 to 200°C, and the reaction time thereof is in the range of 0.5 to 24 hours.
  • the compound (4-c) can be isolated by performing post treatments such as filtration of the precipitate, drying thereof and the like.
  • the isolated compound (4-c) can also be further purified by chromatography, re-crystallization and the like.
  • a compound (16) can be produced by reacting a compound (M5) with thionyl chloride (hereinafter, referred to as a compound (M6)) or oxalyl chloride
  • R 14 represents the same meaning as described above .
  • reaction is carried out in the presence of a solvent or in the absence of a solvent.
  • solvent to be used in the reaction examples include ethers such as THF, ethylene glycol dimethyl ether, 1,4-dioxane and the like, aromatic hydrocarbons such as toluene, xylene and the like, halogenated hydrocarbons such as dichloromethane , chloroform, chlorobenzene , dichlorobenzene and the like and mixtures thereof.
  • ethers such as THF, ethylene glycol dimethyl ether, 1,4-dioxane and the like
  • aromatic hydrocarbons such as toluene, xylene and the like
  • halogenated hydrocarbons such as dichloromethane , chloroform, chlorobenzene , dichlorobenzene and the like and mixtures thereof.
  • the compound (M6) or the compound (M7) is used usually in a proportion of 1 to 20 mol with respect to 1 mol of the compound (M5) .
  • the reaction temperature of the reaction is usually in the range of 0 to 150°C, and the reaction time thereof is in the range of 0.1 to 24 hours.
  • the compound (16) can be isolated by performing post treatments such as distillation off of the solvent and the compound (M6) or the compound (M7), and the like.
  • the isolated compound (16) can also be further purified by distillation and the like.
  • a compound (12-e) can be produced by reacting a compound (12-b) with sodium azide.
  • R 1 , R 2 , R 3 , R , R 5 , R 6 " b and R 14 represent the same meaning as described above.
  • the reaction is carried out usually in the presence of a solvent.
  • solvent to be used in the reaction examples include THF, nitriles such as acetonitrile and the like, acid amides such as DMF, NMP and the like, sulfoxides such as DMSO and the like, ethers such as ethylene glycol dimethyl ether, 1,4-dioxane and the like, water and mixtures thereof.
  • Sodium azide is used usually in a proportion of 1 to 10 mol with respect to 1 mol of the compound (12-b) .
  • the reaction temperature of the reaction is usually in the range of 0 to 100°C, and the reaction time thereof is in the range of 0.5 to 24 hours.
  • the compound (12- e) can be isolated by performing post treatment
  • the isolated compound (12-e) can also be further purified by
  • Ph represents a phenyl group .
  • H H H H H H CH CH 2 0 0
  • H H H H H H CH CHCH 3 0 0
  • H H H H H H H CH 2 CH 2 CH CH 2 0 0
  • H H H H -C ( 0) OCH 3 H cyclopropyl 0 0

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Abstract

A pyrone compound represented by formula (1) has an excellent controlling effect on pests. Since the compound of formula (1) has a controlling activity on pests, the compound is useful as an active ingredient of a pest control agent.

Description

DESCRIPTION
PYRONE COMPOUND AND ITS USE FOR PEST CONTROL
Technical Field
The present invention relates to a pyrone compound and its use for pest control.
Background Art
With the aim of pest control, various compounds have heretofore been investigated and put into practical uses .
Journal of Heterocyclic Chemistry (1996), (33), 1707-1710 discloses a certain kind of pyrone compounds. Disclosure of Invention
The present invention has an object of providing a novel compound having an excellent controlling effect on pests .
The present inventors have intensively studied to solve the above-described problem and resultantly found that a pyrone compound represented by following formula (1) has an excellent controlling effect on pests, leading to completion of the present invention.
That is, the present invention relates to the following inventions.
[1] A pyrone compound represented by formula (1):
Figure imgf000003_0001
wherein ,
Q1 represents an oxygen atom or sulfur atom,
n represents 0 or 1,
R1 , R2 , R3 and R4 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, C3-C6
alicyclic hydrocarbon group optionally substituted by at least one halogen atom, phenyl group optionally
substituted by at least one member selected from Group X, 5-membered heterocyclic group optionally substituted by at least one member selected from Group X, 6-membered heterocyclic group optionally substituted by at least one member selected from Group X, hydrogen atom, halogen atom, nitro group, cyano group, -L1 R9 or -C(=0)R10;
here, L1 represents an oxygen atom, -S(0)m- or - NR11-,
m represents 0, 1 or 2,
R9 represents a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, phenyl group optionally substituted by at least one member selected from Group X, 5-membered heterocyclic group optionally substituted by at least one member selected from Group X, 6-membered heterocyclic group optionally substituted by at least one member selected from Group X or hydrogen atom (with the proviso that R9 does not represent a hydrogen atom when L1 is -S(0)m- and m is 1 or 2 ) ,
R10 represents a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, Cl- C6 alkoxy group optionally substituted by at least one halogen atom, C1-C6 alkylamino group optionally
substituted by at least one halogen atom, C2-C8
dialkylamino group optionally substituted by at least one halogen atom, hydrogen atom, hydroxy group or amino group,
R11 represents a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, or hydrogen atom.
R5 and R6 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, C3-C6 alicyclic hydrocarbon group optionally substituted by at least one halogen atom, phenyl group optionally substituted by at least one member selected from Group X, 5-membered
heterocyclic group optionally substituted by at least one member selected from Group X, 6-membered
heterocyclic group optionally substituted by at least one member selected from Group X, hydrogen atom, halogen atom, nitro group, cyano group, -L R12 or -C(=0)R10,
here, L2 represents an oxygen atom, -S(0)m- or - NR13 - (m and R10 represent the same meaning as described above) , R12 and R13 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted by at least one member selected from Group W, C3-C6 alicyclic hydrocarbon group optionally substituted by at least one member selected from Group a, phenyl group optionally substituted by at least one member selected from Group X, 5-membered heterocyclic group optionally substituted by at least one member selected from Group X, 6-membered heterocyclic group optionally substituted by at least one member selected from Group X, or
hydrogen atom (with the proviso that R12 does not represent a hydrogen atom when L2 is -S(0)m- and m is 1 or 2), alternatively, R12 and R13 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected.
R7 and R8 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted by at least one member selected from Group W, hydrogen atom, or -L3 R14 , alternatively, R7 and R8 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected;
here, L3 represents -C(=Q3)- or -S(0)2-,
Q3 represents an oxygen atom or sulfur atom, R14 represents a C1-C6 chain hydrocarbon group optionally substituted by at least one member selected from Group W, C3-C6 alicyclic hydrocarbon group
optionally substituted by at least one member selected from Group a, phenyl group optionally substituted by at least one member selected from Group X, 5-membered heterocyclic group optionally substituted by at least one member selected from Group X, 6-membered
heterocyclic group optionally substituted by at least one member selected from Group X, hydrogen atom or - L4 R15 (with the proviso that R14 does not represent a hydrogen atom when L3 is -S(0)2-; and except that -NR7R8 is -NHCOC6H5) ,
L4 represents an oxygen atom or -NR16-,
R15 and R16 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted by at least one member selected from Group , C3-C6 alicyclic hydrocarbon group optionally substituted by at least one member selected from Group a, phenyl group optionally substituted by at least one member selected from Group X, 5-membered heterocyclic group optionally substituted by at least one member selected from Group X, 6-membered heterocyclic group optionally substituted by at least one member selected from Group X, or
hydrogen atom, alternatively, R15 and R16 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected;
Group X: the group consisting of C1-C4 alkyl groups optionally substituted by at least one halogen atom, Cl- C4 alkoxy groups optionally substituted by at least one halogen atom, cyano group, nitro group and halogen atoms ;
Group Y: the group consisting of C1-C4 alkoxy groups optionally substituted by at least one halogen atom, Cl- C4 alkylthio groups optionally substituted by at least one halogen atom, benzyloxy group optionally substituted by at least one halogen atom, C2-C6 alkoxy groups optionally substituted by at least one halogen atom, cyano group and halogen atoms;
Group a: the group consisting of C1-C3 alkyl groups, C1-C4 alkoxy groups optionally substituted by at least one halogen atom, C1-C4 alkylthio groups optionally substituted by at least one halogen atom, cyano group and halogen atoms;
Group : the group consisting of C1-C4 alkoxy groups optionally substituted by at least one halogen atom, Cl- C4 alkylthio groups optionally substituted by at least one halogen atom, benzyloxy group optionally substituted by at least one halogen atom, C2-C6 alkoxy groups optionally substituted by at least one halogen atom, cyano group, halogen atoms, C3-C6 alicyclic hydrocarbon groups optionally substituted by at least one member selected from Group a, phenyl groups optionally
substituted by at least one member selected from Group X, 5-membered heterocyclic groups optionally substituted by at least one member selected from Group X and 6- membered heterocyclic groups optionally substituted by at least one member selected from Group X.
(hereinafter, referred to as the inventive compound) .
[2] The pyrone compound according to [1], wherein Q1 is an oxygen atom, in formula (1) . .
[3] The pyrone compound according to [1] or [2], wherein R2 is a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, phenyl group optionally substituted by at least one member selected from Group X, hydrogen atom, halogen atom, nitro group, cyano group or -L1 R9 (here, L1 and R9 are the same meaning as defined in [1] ) , in formula (1) .
[4] The pyrone compound according to any one of [1] to [3], wherein R6 is a hydrogen atom, halogen atom, cyano group or -L2R12 (here, L2 and R12 are the same meaning as defined in [1] . ) , in formula (1) .
[5] The pyrone compound according to any one of [1] to [4], wherein R5 is a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, hydrogen atom, halogen atom or -C(=0)R10 (here, R10 is the same meaning as defined in [1]), in formula (1).
[6] The pyrone compound according to any one of [1] to [5], wherein R1 , R3 and R4 are the same or different and are a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, hydrogen atom, halogen atom, nitro group, cyano group or -L1 R9 (here, L1 and R9 are the same meaning as defined in [1]), in formula ( 1 ) . [7] The pyrone compound according to any one of [1] to [4], wherein R1 , R3 , R4 and R5 are the same or different and are a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, hydrogen atom or halogen atom, in formula (1) .
[8] The pyrone compound according to [1] or [2], wherein R1 , R3 , R4 and R5 are hydrogen atoms, R2 is a hydrogen atom or halogen atom, and R6 is a hydrogen atom, halogen atom or -L2 R12 (here, L1 , R9 , L2 and R12 are the same meaning as defined in [1] ) , in formula (1) .
[9] The pyrone compound according to [1] or [2], wherein R1 , R , R3 , R , R5 and R6 are hydrogen atoms, in formula ( 1 ) .
[10] The pyrone compound according to any one of [1] to [9], wherein R7 and R8 are the same or different and are a C1-C3 chain hydrocarbon group optionally
substituted by at least one member selected from Group , hydrogen atom or -L3 R1 , alternatively, R7 and R8 may be bound to form a 5-membered heterocyclic ring
optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected,
R14 is a C1-C6 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group Z, C3-C6 alicyclic hydrocarbon group optionally substituted by at least one member selected from Group a, phenyl group optionally substituted by at least one member selected from Group X, 5-membered heterocyclic group optionally substituted by at least one member selected from Group X, 6-membered heterocyclic group optionally substituted by at least one member selected from Group X or -L4 R15 (with the proviso that compounds in which R7 is a hydrogen atom, R8 is -C(=0)R1 and R1 is a phenyl group are excluded) ,
R15 is a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group W, C3-C6 alicyclic hydrocarbon group optionally
substituted by at least one member selected from Group a, phenyl group optionally substituted by at least one member selected from Group X, 5-membered heterocyclic group optionally substituted by at least one member selected from Group X or 6-membered heterocyclic group optionally substituted by at least one member selected from Group X,
R16 is a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, or hydrogen atom, alternatively, R15 and R16 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected
(here, L3 and L4 are the same meaning as defined in
[1] ) , Group Z: the group consisting of C3-C6 alicyclic hydrocarbon groups optionally substituted by at least one member selected from Group a, phenyl groups
optionally substituted by at least one member selected from Group X, 5-membered heterocyclic groups optionally substituted by at least one member selected from Group X and 6-membered heterocyclic groups optionally
substituted by at least one member selected from Group X,
in formula ( 1 ) .
[11] The pyrone compound according to any one of [1] to [9], wherein R7 and R8 are the same or different and are a C1-C3 chain hydrocarbon group optionally
substituted by at least one member selected from Group Y, hydrogen atom or -L3 R14 , alternatively, R7 and R8 may be bound to form a 5-membered heterocyclic ring
optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected,
Q3 is an oxygen atom,
R14 is a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, C3-C6 alicyclic hydrocarbon group optionally
substituted by at least one member selected from Group a, or -L4 R1 ,
R15 is a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group W or C3-C6 alicyclic hydrocarbon group optionally
substituted by at least one member selected from Group a,
R16 is a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y or hydrogen atom (here, L3 and L4 are the same meaning as defined in [1] .), in formula (1) .
[12] The pyrone compound according to any one of [1] to [9], wherein R7 and R8 are the same or different and are a C1-C3 chain hydrocarbon group optionally
substituted by at least one member selected from Group Y, hydrogen atom or -L3 R14 ,
Q3 is an oxygen atom,
R14 is a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, cyclopropyl group optionally substituted by at least one member selected from Group a or -L R15 ,
R15 is a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group W or cyclopropyl group optionally substituted by at least one member selected from Group a,
R16 is a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y or hydrogen atom (here, L3 and L4 are the same meaning as defined in [1] .) , in formula (1) .
[13] A pest control agent comprising the pyrone compound as described in any one of [1] to [12] and an inert carrier.
[14] Use of the pyrone compound as described in any one of [1] to [12] for control pests.
[15] A pest control method comprising applying an effective amount of the pyrone compound as described in any one of [1] to [12] to pests or areas where pests live .
Since the inventive compound has a controlling activity on pests, the compound is useful as an active ingredient of a pest control agent.
Mode of Carrying Out the Invention
Substituents used in the description of the present specification will be explained by examples mentioned below. In the present specification, "halogen atom" means a fluorine atom, chlorine atom, bromine atom or iodine atom, "heterocyclic group" means a mono-valent group having a structure obtained by removing one hydrogen atom existing on a ring of a heterocyclic compound, and "hydrocarbon group" means a mono-valent group having a structure obtained by removing one hydrogen atom existing on a hydrocarbon compound.
In the present specification, "C3-C6" in "C3-C6 alicyclic hydrocarbon group" means that the number of carbon atoms constituting a ring of an alicyclic hydrocarbon group is in the range of 3 to 6.
Examples of "C1-C6 chain hydrocarbon group
optionally substituted by at least one halogen atom" include C1-C6 alkyl groups optionally substituted by at least one halogen atom such as a methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, 1-methylbutyl group, 2-methylbutyl group, isopentyl group, tert-pentyl group, neopentyl group, hexyl group, isohexyl group, fluoromethyl group,
difluoromethyl group, trifluoromethyl group, 2,2,2- trifluoroethyl group, pentafluoroethyl group,
chloromethyl group, trichloromethyl group and 2,2,2- trichloroethyl group and the like;
C2-C6 alkenyl groups optionally substituted by at least one halogen atom such as an ethenyl group, 1- propenyl group, 2-propenyl group, 1-butenyl group, 2- butenyl group, 3-butenyl group, 1-methylethenyl group, 1-methylpropenyl group, 1 , 2-dimethylpropenyl group, 2- methyl-2-propenyl group, 3-methyl-2-butenyl group, 2,3- dimethyl-2-butenyl group, 2-pentenyl group, 2-hexenyl group, 2 , 2-difluoroethenyl group, 2 , 2 -dichloroethenyl group and 3 , 3 , 3-trifluoro-l-propenyl group and the like;
C2-C6 alkynyl groups optionally substituted by at least one halogen atom such as an ethynyl group, 1- propynyl group, 2-propynyl group, 1-butynyl group, 2- butynyl group, 3-butynyl group, 3 , 3 , 3-trifluoro-1- propynyl group and 3 , 3 , 3-trichloro- 1-propynyl group and the like.
Examples of "C3-C6 alicyclic hydrocarbon group optionally substituted by at least one halogen atom" include a cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 2,2- difluorocyclopropyl group, 2,2,3,3- tetrafluorocyclopropyl group, 2 , 2-dichlorocyclopropyl group and 2 , 2 , 3 , 3-tetrachlorocyclopropyl group.
Examples of "phenyl group optionally substituted by at least one member selected from Group X" include a phenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4 -fluorophenyl group, 2-chlorophenyl group, 3- chlorophenyl group, 4 -chlorophenyl group, 2-methylphenyl group, 3-methylphenyl group, 4 -methylphenyl group, 2- methoxyphenyl group, 3-methoxyphenyl group, 4- methoxyphenyl group, 2 -( tri fluoromethyl ) phenyl group, 3- (trifluoromethyl ) phenyl group, 4 -( tri fluoromethyl ) phenyl group, 2- (trifluoromethoxy) phenyl group, 3- ( trifluoromethoxy) phenyl group, 4-
( trifluoromethoxy) phenyl group, 2-nitrophenyl group, 3- nitrophenyl group, 4 -nitrophenyl group, 2-cyanophenyl group, 3-cyanophenyl group and 4 -cyanophenyl group.
Examples of "5-membered heterocyclic group
optionally substituted by at least one member selected from Group X" include 5-membered saturated heterocyclic groups such as a pyrrolidin-l-yl group, tetrahydrofuran- 2-yl group, tetrahydrofuran-3-yl group, 2,2- difluorotetrahydrofuran-5-yl group, 2,2- difluorotetrahydrofuran-3-yl group and 3,3- difluorotetrahydrofuran-4 -yl group and the like;
5-membered aromatic heterocyclic groups such as a pyrazol-l-yl group, 3-methylpyrazol-l-yl group, 4- methylpyrazol-l-yl group, 5-methylpyrazol-l-yl group, 3- fluoropyrazol-l-yl group, 4-fluoropyrazol-l-yl group, 5- fluoropyrazol-l-yl group, 3-chloropyrazol-l-yl group, 4- chloropyrazol-l-yl group, 5-chloropyrazol-l-yl group, 3- cyanopyrazol-l-yl group, 4-cyanopyrazol-l-yl group, 5- cyanopyrazol-l-yl group, pyrrol-l-yl group, 2- methylpyrrol-l-yl group, 3-methylpyrrol-l-yl group, 2- fluoropyrrol-l-yl group, 3-fluoropyrrol-l-yl group, 2- chloropyrrol-l-yl group, 3-chloropyrrol-l-yl group, 2- cyanopyrrol-l-yl group, 3-cyanopyrrol-l-yl group, 1,2,4- triazol-l-yl group, 3-methyl-l , 2 , 4-triazol-l-yl group, 5-methyl-l , 2 , 4-triazol-l-yl group, 3-fluoro-1 , 2 , 4- triazol-l-yl group, 5-fluoro-1 , 2 , 4-triazol-l-yl group, 3-chloro-l , 2 , 4-triazol-l-yl group, 5-chloro-l , 2 , 4- triazol-l-yl group, 3-cyano- 1 , 2 , -triazol- 1-yl group, 5- cyano-1 , 2 , 4-triazol-l-yl group, 1 , 2 , 3 , 4-tetrazol-l-yl group, 5-methyl-l, 2 , 3, 4-tetrazol-l-yl group, 5-fluoro-
1.2.3.4-tetrazol-l-yl group, 5-chloro-l , 2 , 3 , 4 -tetrazol- 1-yl group, 5-cyano-l , 2 , 3 , 4 -tetrazol- 1-yl group,
1.2.3.5-tetrazol-l-yl group, 4 -methyl-1 , 2 , 3 , 5-tetrazol- 1-yl group, 4-fluoro-1 , 2 , 3 , 5-tetrazol-l-yl group, 4- chloro-1 , 2 , 3 , 5-tetrazol-l-yl group, 4 -cyano- 1 , 2 , 3 , 5- tetrazol-l-yl group, furan-2-yl group, 3-methylfuran-2- yl group, 4-methylfuran-2-yl group, 5-methylfuran-2-yl group, 3-fluorofuran-2-yl group, 4-fluorofuran-2-yl group, 5-fluorofuran-2-yl group, 3-chlorofuran-2-yl group, 4-chlorofuran-2-yl group, 5-chlorofuran-2-yl group, 3-cyanofuran-2-yl group, -cyanofuran-2-yl group, 5-cyanofuran-2-yl group, furan-3-yl group, 2- methylfuran-3-yl group, 4-methylfuran-3-yl group, 5- methylfuran-3-yl group, 2-fluorofuran-3-yl group, 4- fluorofuran-3-yl group, 5-fluorofuran-3-yl group, 2- chlorofuran-3-yl group, 4-chlorofuran-3-yl group, 5- chlorofuran-3-yl group, 2-cyanofuran-3-yl group, 4- cyanofuran-3-yl group, 5-cyanofuran-3-yl group,
thiophen-2-yl group, 3-methylthiophen-2-yl group, 4- methylthiophen-2-yl group, 5-methylthiophen-2 -yl group, 3-fluorothiophen-2-yl group, 4 -fluorothiophen-2-yl group, 5-fluorothiophen-2-yl group, 3-chlorothiophen-2- yl group, 4-chlorothiophen-2-yl group, 5-chlorothiophen- 2-yl group, 3-cyanothiophen-2 -yl group, 4 -cyanothiophen-
2-yl group, 5-cyanothiophen-2-yl group, thiophen-3-yl group, 2-methylthiophen-3-yl group, 4 -methylthiophen-3- yl group, 5-methylthiophen-3-yl group, 2-fluorothiophen-
3-yl group, 4-fluorothiophen-3-yl group, 5- fluorothiophen-3-yl group, 2-chlorothiophen-3-yl group,
4-chlorothiophen-3-yl group, 5-chlorothiophen-3-yl group, 2-cyanothiophen-3-yl group, 4-cyanothiophen-3-yl group and 5-cyanothiophen-3-yl group and the like.
Examples of "6-membered heterocyclic group
optionally substituted by at least one member selected from Group X" include 6-membered saturated heterocyclic groups such as a piperidin-l-yl group, morpholyl group, thiomorpholyl group and 4-methylpiperazin-l-yl group and the like;
6-membered aromatic heterocyclic groups such as a pyridin-2-yl group, 3-methylpyridin-2-yl group, 4- methylpyridin-2-yl group, 5-methylpyridin-2-yl group, 6- methylpyridin--2 -yl group, 3-fluoropyridin-2-yl group, 4- fluoropyridin-2-yl group, 5-fluoropyridin-2 -yl group, 6- fluoropyridin-2 -yl group, 3-chloropyridin-2-yl group, 4- chloropyridin-2 -yl group, 5-chloropyridin-2-yl group, 6- chloropyridin-2 -yl group, 3-cyanopyridin-2-yl group, 4- cyanopyridin-2-yl group, 5-cyanopyridin-2-yl group, 6- cyanopyridin-2-yl group, pyridin-3-yl group, 2- methylpyridin-3-yl group, 4 -methylpyridin-3-yl group, 5- methylpyridin-3-yl group, 6-methylpyridin-3-yl group, 2- fluoropyridin-3-yl group, 4 -fluoropyridin-3-yl group, 5- fluoropyridin-3-yl group, 6-fluoropyridin-3-yl group, 2- chloropyridin-3-yl group, 4-chloropyridin-3-yl group, 5- chloropyridin-3-yl group, 6-chloropyridin-3-yl group, 2- cyanopyridin-3-yl group, 4-cyanopyridin-3-yl group, 5- cyanopyridin-3-yl group, 6-cyanopyridin-3-yl group, pyridin-4-yl group, 2-methylpyridin-4 -yl group, 3- methylpyridin-4 -yl group, 2-fluoropyridin-4 -yl group, 3- fluoropyridin-4 -yl group, 2-chloropyridin-4-yl group, 3- chloropyridin-4 -yl group, 2-cyanopyridin-4-yl group, 3- cyanopyridin-4-yl group, pyrazin-2-yl group, 3- methylpyrazin-2-yl group, 5-methylpyrazin-2-yl group, 6- methylpyrazin-2 -yl group, 3-fluoropyrazin-2-yl group, 5- fluoropyrazin-2-yl group, 6-fluoropyrazin-2-yl group, 3- chloropyrazin-2-yl group, 5-chloropyrazin-2-yl group, 6- chloropyrazin-2-yl group, 3-cyanopyrazin-2-yl group, 5- cyanopyrazin-2-yl group, 6-cyanopyrazin-2-yl group, pyrimidin-2-yl group, 4 -methylpyrimidin-2 -yl group, 5- methylpyrimidin-2-yl group, 4-fluoropyrimidin-2 -yl group, 5-fluoropyrimidin-2-yl group, 4 -chloropyrimidin-
2-yl group, 5-chloropyrimidin-2-yl group, 4- cyanopyrimidin-2 -yl group, 5-cyanopyrimidin-2-yl group, pyrimidin-4-yl group, 2-methylpyrimidin-4-yl group, 5- methylpyrimidin-4-yl group, 6-methylpyrimidin-4-yl group, 2-fluoropyrimidin-4-yl group, 5-fluoropyrimidin- 4-yl group, 6-fluoropyrimidin-4-yl group, 2- chloropyrimidin-4 -yl group, 5-chloropyrimidin-4-yl group, 6-chloropyrimidin-4-yl group, 2-cyanopyrimidin-4 - yl group, 5-cyanopyrimidin-4-yl group, 6-cyanopyrimidin-
4-yl group, pyrimidin- 5-yl group, 2-methylpyrimidin-5-yl group, 4 -methylpyrimidin-5-yl group, 2-fluoropyrimidin-
5-yl group, 4-fluoropyrimidin-5-yl group, 2- chloropyrimidin-5-yl group, 4-chloropyrimidin-5-yl group, 2-cyanopyrimidin-5-yl group, 4 -cyanopyrimidin-5- yl group, pyridazin-3-yl group, 4-methylpyridazin-3-yl group, 5-methylpyridazin-3-yl group, 6-methylpyridazin-
3-yl group, 4-fluoropyridazin-3-yl group, 5- fluoropyridazin-3-yl group, 6-fluoropyridazin-3-yl group, 4-chloropyridazin-3-yl group, 5-chloropyridazin-
3-yl group, 6-chloropyridazin-3-yl group, 4- cyanopyridazin-3-yl group, 5-cyanopyridazin-3-yl group,
6-cyanopyridazin-3-yl group, pyridazin-4-yl group, 3- methylpyridazin-4-yl group, 5-methylpyridazin-4-yl group, 6-methylpyridazin-4-yl group, 3-fluoropyridazin-
4-yl group, 5-fluoropyridazin-4 -yl group, 6- fluoropyridazin-4 -yl group, 3-chloropyridazin-4-yl group, 5-chloropyridazin-4-yl group, 6-chloropyridazin- 4-yl group, 3-cyanopyridazin-4-yl group, 5- cyanopyridazin-4-yl group and 6-cyanopyridazin-4-yl group and the like.
Examples of "C1-C6 alkoxy group optionally
substituted by at least one halogen atom" include C1-C6 alkoxy groups optionally substituted by at least one halogen atom such as a methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, 1-methylbutoxy group, 2-methylbutoxy group, isopentyloxy group, tert-pentyloxy group, neopentyloxy group, hexyloxy group, isohexyloxy group, fluoromethoxy group, difluoromethoxy group, trifluoromethoxy group, 2 , 2 , 2-trifluoroethoxy group, pentafluoroethoxy group, chloromethoxy group, dichloromethoxy group,
trichloromethoxy group and 2 , 2 , 2 -trichloroethoxy group and the like;
C2-C6 alkenyloxy groups optionally substituted by at least one halogen atom such as an ethenyloxy group, 1- propenyloxy group, 2-propenyloxy group, 1-butenyloxy group, 2-butenyloxy group, 3-butenyloxy group, 1-methyl- 1-ethenyloxy group, 1-methyl-l-propenyloxy group, 1,2- dimethyl-l-propenyloxy group, 2-methyl-2-propenyloxy group, 3-methyl-2-butenyloxy group, 2 , 3-dimethyl-2- butenyloxy group, 2-pentenyloxy group, 2,2- difluoroethenyloxy group, 2 , 2 -dichloroethenyloxy group and 3, 3, 3-trifluoro-l-propenyloxy group and the like;
C2-C6 alkynyloxy groups optionally substituted by at least one halogen atom such as an ethynyloxy group, 1- propynyloxy group, 2-propynyloxy group, 1-butynyloxy group, 2-butynyloxy group, 3-butynyloxy group, 3,3,3- trifluoropropynyloxy group and 3,3,3- trichloropropynyloxy group and the like.
Examples of "C1-C6 alkylamino group optionally substituted by at least one halogen atom" include C1-C6 alkylamino groups optionally substituted by at least one halogen atom such as a methylamino group, ethylamino group, propylamino group, isopropylamino group,
butylamino group, isobutylamino group, see-butylamino group, tert-butylamino group, pentylamino group, 1- methylbutylamino group, 2-methylbutylamino group, isopentylamino group, tert-pentylamino group,
neopentylamino group, hexylamino group, isohexylamino group, 2 , 2 , 2-trifluoroethylamino group and 2,2,2- trichloroethylamino group and the like;
C3-C6 alkenylamino groups optionally substituted by at least one halogen atom such as a 2-propenylamino group, 2 -butenylamino group, 3-butenylamino group, 2- methyl-2-propenylamino group, 3-methyl-2-butenylamino group, 2 , 3-dimethyl-2 -butenylamino group, 2- pentenylamino group, 2-hexenylamino group and 3,3- difluoro2-propenylamino group and the like;
C3-C6 alkynylamino groups optionally substituted by at least one halogen atom such as a 2 -propynylamino group, 2-butynylamino group and 3-butynylamino group and the like. Examples of "C2-C8 dial kylamino group optionally substituted by at least one halogen atom" include a dimethylamino group, diethylamino group, dipropylamino group, dibutylamino group and bis (2,2,2- trifluoroethyl) amino group.
Examples of "C1-C6 chain hydrocarbon group
optionally substituted by at least one member selected from Group " include a methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group,
1-methylbutyl group, 2 -methylbutyl group, isopentyl group, tert-pentyl group, neopentyl group, hexyl group, isohexyl group, fluoromethyl group, difluoromethyl group, trifluoromethyl group, 2 , 2 , 2-trifluoroethyl group, pentafluoroethyl group, chloromethyl group, trichloromethyl group, 2 , 2 , 2-trichloroethyl group, 2- chloroethyl group, 2-bromoethyl group, 3-chloropropyl group, 3-bromopropyl group, 4 -chlorobutyl group, 4- bromobutyl group, ethenyl group, 1-propenyl group, 2- propenyl group, 1-butenyl group, 2-butenyl group, 3- butenyl group, 1-methylethenyl group, 1-methylpropenyl group, 2-methylpropenyl group, 1 , 2 -dimethylpropenyl group, 2-methyl-2-propenyl group, 3-methyl-2-butenyl group, 2 , 3-dimethyl-2 -butenyl group, 2-pentenyl group,
2-hexenyl group, 1-fluoroethenyl group, 1,2- difluoroethenyl group, 2 , 2-difluoroethenyl group, 1,2,2 trifluoroethenyl group, 1-chloroethenyl group, 1,2- dichloroethenyl group, 2 , 2 -dichloroethenyl group, 1,2,2 trichloroethenyl group, 1, 2-difluoropropenyl group, 3 , 3 , 3-trifluoropropenyl group, ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, methoxymethyl group, 1- methoxyethyl group, 2-methoxyethyl group, 1- methoxypropyl group, 2-methoxypropyl group, 3- methoxypropyl group, 1-methoxybutyl group, 2- methoxybutyl group, 3-methoxybutyl group, ethoxymethyl group, 1-ethoxyethyl group, 2 -ethoxyethyl group, 1- ethoxypropyl group, 2-ethoxypropyl group, 3-ethoxypropyl group, 1-ethoxybutyl group, 2-ethoxybutyl group, 3- ethoxybutyl group, fluoromethoxymethyl group,
difluoromethoxymethyl group, trifluoromethoxymethyl group, 2 , 2 ,2-trifluoroethoxymethyl group,
chloromethoxymethyl group, dichloromethoxymethyl group, trichloromethoxymethyl group, 2,2,2- trichloroethoxymethyl group, 2 -propenyloxymethyl group, 2-butenyloxymethyl group, 3-butenyloxymethyl group, 2- propynyloxymethyl group, methylthiomethyl group, 1- methylthioethyl group, 2-methylthioethyl group, 1- methylthiopropy1 group, 2 -methylthiopropyl group, 3- methylthiopropyl group, 1-methylthiobutyl group,
ethylthiomethyl group, 1-ethylthioethyl group, 1- ethylthiopropyl group, 1-ethylthiobutyl group,
benzyloxymethyl group, cyanomethyl group, 1-cyanoethyl group, 2-cyanoethyl group, 1-cyanopropyl group, 2- cyanopropyl group, 3-cyanopropyl group, 1-cyanobutyl group, 1-cyanopentyl group, 1-cyanohexyl group,
cyclopropylmethyl group, 1-cyclopropylethyl group, 2- cyclopropylethyl group, 1-cyclopropylpropyl group, 2- cyclopropylpropyl group, 3-cyclopropylpropyl group, cyclobutylmethyl group, 1-cyclobutylethyl group, 2- cyclobutylethyl group, 2 , 2-difluorocyclopropylmethyl group, 1 , 2 , 2 , 3 , 3-pentafluorocyclopropylmethyl group, 2 , 2-dichlorocyclopropylmethyl group, 1,2,2,3,3- pentachlorocyclopropylmethyl group, phenylmethyl group,
(2-fluorophenyl ) methyl group, ( 3-fluorophenyl ) methyl group, ( 4-fluorophenyl ) methyl group, (2- chlorophenyl ) methyl group, ( 3-chlorophenyl ) methyl group,
( 4 -chlorophenyl ) methyl group, ( 2 -methylphenyl ) methyl group, ( 3-methylphenyl ) methyl group, (4- methylphenyl ) methyl group, ( 2 -methoxyphenyl ) methyl group, ( 3-methoxyphenyl ) methyl group, (4- methoxyphenyl ) methyl group, 2 -phenylethyl group,
(pyridin-2-yl ) -methyl group, (pyridin-3-yl ) -methyl group, (pyridin-4-yl ) -methyl group, ( thiophen-2 -yl ) - methyl group, ( thiophen-3-yl ) -methyl group, (furan-2- yl) -methyl group, ( furan-3-yl ) -methyl group,
(tetrahydrofuran-2-yl) -methyl group and
( tetrahydrofuran-3-yl ) -methyl group.
Examples of the 5-membered heterocyclic ring or 6- membered heterocyclic ring in "R7 and R8 may be bound to form a 5-membered heterocyclic ring optionally
substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected" include rings represented by following formulae (a) to (t) . (Here, Q3 and R16 represent the same meaning as described above, and A1 represents a nitrogen atom to which R7 and R8 are connected. )
Figure imgf000025_0001
(o) (P) (q) (r) (s) (t)
Examples of the 5-membered heterocyclic ring or 6- membered heterocyclic ring in "R12 and R13 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected" include rings represented by following formulae (u) to (x) . (Here, A2 represents a nitrogen atom to which R12 and R13 are connected.)
Figure imgf000025_0002
(U) (V) (W) (X) Examples of the 5-membered heterocyclic ring or 6- membered heterocyclic ring in "R15 and R16 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected" include rings represented by following formulae (al) to (a4). (Here, A3 represents a nitrogen atom to which R15 and R16 are connected.)
Figure imgf000026_0001
(a1 ) (a2) (a3) (a4)
Examples of "C3-C6 alicyclic hydrocarbon group optionally substituted by at least one member selected from Group a" include a cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group,
methylcyclopropyl group, 2-methylcyclopropyl group, 2,2 dimethylcyclopropyl group, 2 , 2 , 3-trimethylcyclopropyl group, 2 , 2 , 3 , 3-tetramethylcyclopropyl group, 1,2,2,3,3- pentamethylcyclopropyl group, 1-fluorocyclopropyl group 2-fluorocyclopropyl group, 2 , 2-difluorocyclopropyl group, 2 , 2 , 3-trifluorocyclopropyl group, 2,2,3,3- tetrafluorocyclopropyl group, 2 , 2-dichlorocyclopropyl group, 2 , 2 , 3 , 3-tetrachlorocyclopropyl group,
cyanocyclopropyl group, 2 -cyanocyclopropyl group, 2,2- dicyanocyclopropyl group, 1-methoxycyclopropyl group, 2 methoxycyclopropyl group, 1-ethoxycyclopropyl group, 1- methylcyclobutyl group, 1-methylcyclopentyl group, 1- methylcyclohexyl group, 2-methylcyclohexyl group, 3- methylcyclohexyl group and 4 -methylcyclohexyl group. Examples of "C1-C3 alkyl group" include a methyl group, ethyl group and propyl group.
Examples of "C1-C4 alkyl group optionally
substituted by at least one halogen atom" include a methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, fluoromethyl group, difluoromethyl group, trifluoromethyl group, 2 , 2 , 2-trifluoroethyl group, pentafluoroethyl group, chloromethyl group, dichloromethyl group, trichloromethyl group and 2,2,2- trichloroethyl group.
Examples of "C1-C4 alkoxy group optionally
substituted by at least one halogen atom" include a methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, fluoromethoxy group, difluoromethoxy group, trifluoromethoxy group, 2 , 2 , 2-trifluoroethoxy group, pentafluoroethoxy group, chloromethoxy group, trichloromethoxy group and 2 , 2 , 2 -trichloroethoxy group.
Examples of "C1-C4 alkylthio group optionally substituted by at least one halogen atom" include a methylthio group, ethylthio group, propylthio group, isopropylthio group, butylthio group and 2,2,2- trifluoroethylthio group.
"Benzyloxy group optionally substituted by at least one halogen atom" includes a benzyloxy group, 2- chlorophenylmethoxy group, 3-chlorophenylmethoxy group and 4 -chlorophenylmethoxy group.
The present invention also relates to the following inventions .
[1-2] A pyrone compound represented by formula (1):
Figure imgf000028_0001
wherein ,
Q1 represents an oxygen atom or sulfur atom,
n represents 0 or 1,
R1 , R2 , R3 and R4 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, C3-C6
alicyclic hydrocarbon group optionally substituted by at least one halogen atom, phenyl group optionally
substituted by at least one member selected from Group X, 5-membered heterocyclic group optionally substituted by at least one member selected from Group X, 6-membered heterocyclic group optionally substituted by at least one member selected from Group X, hydrogen atom, halogen atom, nitro group, cyano group, -L1 R9 or -C(=0)R10;
here, L1 represents an oxygen atom, -S(0)m- or - NR11-,
m represents 0, 1 or 2,
R9 represents a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, phenyl group optionally substituted by at least one member selected from Group X, 5-membered heterocyclic group optionally substituted by at least one member selected from Group X, 6-membered heterocyclic group optionally substituted by at least one member selected from Group X or hydrogen atom (with the proviso that R9 does not represent a hydrogen atom when L1 is -S(0)m- and m is 1 or 2 ) ,
R10 represents a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, Cl- C6 alkoxy group optionally substituted by at least one halogen atom, C1-C6 alkylamino group optionally
substituted by at least one halogen atom, C2-C8
dialkylamino group optionally substituted by at least one halogen atom, hydrogen atom, hydroxy group or amino group,
R11 represents a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, or hydrogen atom.
R5 and R6 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, C3-C6 alicyclic hydrocarbon group optionally substituted by at least one halogen atom, phenyl group optionally substituted by at least one member selected from Group X, 5-membered
heterocyclic group optionally substituted by at least one member selected from Group X, 6-membered
heterocyclic group optionally substituted by at least one member selected from Group X, hydrogen atom, halogen atom, nitro group, cyano group, -L2 R12 or -C(=0)R10,
here, L2 represents an oxygen atom, -S(0)m- or - NR13 - (m and R10 represent the same meaning as described above) ,
R12 and R13 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted by at least one member selected from Group W, C3-C6 alicyclic hydrocarbon group optionally substituted by at least one member selected from Group a, phenyl group optionally substituted by at least one member selected from Group X, 5-membered heterocyclic group optionally substituted by at least one member selected from Group X, 6-membered heterocyclic group optionally substituted by at least one member selected from Group X, or
hydrogen atom (with the proviso that R12 does not represent a hydrogen atom when L2 is -S(0)m- and m is 1 or 2), alternatively, R12 and R13 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected.
R7 and R8 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted by at least one member selected from Group W, hydrogen atom, or -L3 R14 , alternatively, R7 and R8 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected;
here, L3 represents -C(=Q3)- or -S(0)2-,
Q3 represents an oxygen atom or sulfur atom,
R14 represents a C1-C6 chain hydrocarbon group optionally substituted by at least one member selected from Group W, C3-C6 alicyclic hydrocarbon group
optionally substituted by at least one member selected from Group a, phenyl group optionally substituted by at least one member selected from Group X, 5-membered heterocyclic group optionally substituted by at least one member selected from Group X, 6-membered
heterocyclic group optionally substituted by at least one member selected from Group X, hydrogen atom or - L R15 (with the proviso that R1 does not represent a hydrogen atom when L3 is -S(0)2-; and except that -NR7R8 is -NHCOC6H5) ,
L4 represents an oxygen atom or -NR16-,
R15 and R16 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted by at least one member selected from Group , C3-C6 alicyclic hydrocarbon group optionally substituted by at least one member selected from Group a, phenyl group optionally substituted by at least one member selected from Group X, 5-membered heterocyclic group optionally substituted by at least one member selected from Group X, 6-membered heterocyclic group optionally substituted by at least one member selected from Group X, or
hydrogen atom, alternatively, R15 and R16 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected;
Group X: the group consisting of C1-C4 alkyl groups optionally substituted by at least one halogen atom, Cl- C4 alkoxy groups optionally substituted by at least one halogen atom, cyano group, nitro group and halogen atoms ;
Group Y: the group consisting of C1-C4 alkoxy groups optionally substituted by at least one halogen atom, Cl- C4 alkylthio groups optionally substituted by at least one halogen atom, benzyloxy group optionally substituted by at least one halogen atom, cyano group and halogen atoms ;
Group a: the group consisting of C1-C3 alkyl groups, C1-C4 alkoxy groups optionally substituted by at least one halogen atom, C1-C4 alkylthio groups optionally substituted by at least one halogen atom, cyano group and halogen atoms;
Group W: the group consisting of C1-C4 alkoxy groups optionally substituted by at least one halogen atom, CI- C4 alkylthio groups optionally substituted by at least one halogen atom, benzyloxy group optionally substituted by at least one halogen atom, cyano group, halogen atoms, C3-C6 alicyclic hydrocarbon groups optionally substituted by at least one member selected from Group a, phenyl groups optionally substituted by at least one member selected from Group X, 5-membered heterocyclic groups optionally substituted by at least one member selected from Group X and 6-membered heterocyclic groups optionally substituted by at least one member selected from Group X.
(hereinafter, referred to as the inventive compound) .
[2-2] The pyrone compound according to [1-2], wherein Q1 is an oxygen atom, in formula (1) .
[3-2] The pyrone compound according to [1-2] or [2-
2], wherein R2 is a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, phenyl group optionally substituted by at least one member selected from Group X, hydrogen atom, halogen atom, nitro group, cyano group or -L1 R9 (here, L1 and R9 are the same meaning as defined in [1-2]), in formula (1) .
[4-2] The pyrone compound according to any one of [1-2] to [3-2], wherein R6 is a hydrogen atom, halogen atom, cyano group or -L2 R12 (here, L2 and R12 are the same meaning as defined in [1-2].), in formula (1).
[5-2] The pyrone compound according to any one of [1-2] to [4-2], wherein R5 is a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, hydrogen atom, halogen atom or -C(=0)R10 (here,
R10 is the same meaning as defined in [1-2]), in formula
(1) .
[6-2] The pyrone compound according to any one of [1-2] to [5-2], wherein R1 , R3 and R4 are the same or different and are a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, hydrogen atom, halogen atom, nitro group, cyano group or -L^9 (here, L and R are the same meaning as defined in [1-2]), in formula (1).
[7-2] The pyrone compound according to any one of [1-2] to [4-2], wherein R1 , R3 , R4 and R5 are the same or different and are a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, hydrogen atom or halogen atom, in formula (1) .
[8-2] The pyrone compound according to [1-2] or [2- 2], wherein R1 , R3 , R4 and R5 are hydrogen atoms, R2 is a hydrogen atom or halogen atom, and R6 is a hydrogen atom, halogen atom or -L2 R12 (here, L1 , R9 , L2 and R12 are the same meaning as defined in [1-2]), in formula (1) -
[9-2] The pyrone compound according to [1-2] or [2- 2], wherein R1 , R2 , R3 , R4 , R5 and R6 are hydrogen atoms, in formula (1) .
[10-2] The pyrone compound according to any one of
[1-2] to [9-2], wherein R7 and R8 are the same or different and are a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group , hydrogen atom or -L3 R14 , alternatively, R7 and R8 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected,
R14 is a C1-C6 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group Z, C3-C6 alicyclic hydrocarbon group optionally substituted by at least one member selected from Group a, phenyl group optionally substituted by at least one member selected from Group X, 5-membered heterocyclic group optionally substituted by at least one member selected from Group X, 6-membered heterocyclic group optionally substituted by at least one member selected from Group X or -L4 R15 (with the proviso that compounds in which R7 is a hydrogen atom, R8 is -C(=0)R14 and R14 is a phenyl group are excluded) ,
R15 is a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group , C3-C6 alicyclic hydrocarbon group optionally
substituted by at least one member selected from Group a, phenyl group optionally substituted by at least one member selected from Group X, 5-membered heterocyclic group optionally substituted by at least one member selected from Group X or 6-membered heterocyclic group optionally substituted by at least one member selected from Group X,
R16 is a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, or hydrogen atom, alternatively, R15 and R16 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected
(here, L3 and L4 are the same meaning as defined in [1- 2] ) ,
Group Z: the group consisting of C3-C6 alicyclic hydrocarbon groups optionally substituted by at least one member selected from Group a, phenyl groups
optionally substituted by at least one member selected from Group X, 5-membered heterocyclic groups optionally substituted by at least one member selected from Group X and 6-membered heterocyclic groups optionally
substituted by at least one member selected from Group X,
in formula ( 1 ) .
[11-2] The pyrone compound according to any one of [1-2] to [9-2], wherein R7 and R8 are the same or different and are a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, hydrogen atom or -L3 R14 , alternatively, R7 and R8 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected,
Q3 is an oxygen atom,
R14 is a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, C3-C6 alicyclic hydrocarbon group optionally
substituted by at least one member selected from Group a, or -L4 R15 ,
R15 is a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group W or C3-C6 alicyclic hydrocarbon group optionally
substituted by at least one member selected from Group a,
R16 is a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y or hydrogen atom (here, L3 and L4 are the same meaning as defined in [1-2] . ) , in formula (1) .
[12-2] The pyrone compound according to any one of [1-2] to [9-2], wherein R7 and R8 are the same or different and are a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, hydrogen atom or -L3 R14 ,
Q3 is an oxygen atom,
R1 is a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, cyclopropyl group optionally substituted by at least one member selected from Group a or -L4 R15 ,
R15 is a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group W or cyclopropyl group optionally substituted by at least one member selected from Group a,
R16 is a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y or hydrogen atom (here, L3 and L4 are the same meaning as defined in [1-2].)/ in formula (1).
[13-2] A pest control agent comprising the pyrone compound as described in any one of [1-2] to [12-2] and an inert carrier.
[14-2] Use of the pyrone compound as described in any one of [1-2] to [12-2] for control pests.
[15-2] A pest control method comprising applying an effective amount of the pyrone compound as described in any one of [1-2] to [12-2] to pests or areas where pests live.
Examples of embodiments of the present invention include the following pyrone compounds.
pyrone compounds represented by formula (1) in which
Q1 represents an oxygen atom;
pyrone compounds represented by formula (1) in which Q1 represents a sulfur atom;
pyrone compounds represented by formula (1) in which R1 represents a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, hydrogen atom, halogen atom, nitro group, cyano group or -L1 R9 ;
pyrone compounds represented by formula (1) in which R1 represents a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, hydrogen atom or halogen atom;
pyrone compounds represented by formula (1) in which R1 represents a hydrogen atom;
pyrone compounds represented by formula (1) in which
R3 represents a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, hydrogen atom, halogen atom, nitro group, cyano group or -L1 R9 ;
pyrone compounds represented by formula (1) in which R3 represents a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, hydrogen atom or halogen atom;
pyrone compounds represented by formula (1) in which R3 represents a hydrogen atom;
pyrone compounds represented by formula (1) in which
R4 represents a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, hydrogen atom, halogen atom, nitro group, cyano group or -L1 R9 ;
pyrone compounds represented by formula (1) in which R4 represents a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, hydrogen atom or halogen atom;
pyrone compounds represented by formula (1) in which R4 represents a hydrogen atom;
pyrone compounds represented by formula (1) in which
R5 represents a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, hydrogen atom, halogen atom or -C(=0)R10;
pyrone compounds represented by formula (1) in which R5 represents a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, hydrogen atom or halogen atom;
pyrone compounds represented by formula (1) in which R5 represents a hydrogen atom; pyrone compounds represented by formula (1) in which R1 , R3 and R4 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, hydrogen atom, halogen atom, nitro group, cyano group or -L1 R9 ;
pyrone compounds represented by formula (1) in which R1 , R3 and R4 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, hydrogen atom or halogen atom;
pyrone compounds represented by formula (1) in which Q1 represents an oxygen atom,
R1 , R3 and R4 are the same or different and
represent a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, hydrogen atom or halogen atom;
pyrone compounds represented by formula (1) in which R1 , R3 , R4 and R5 are the same or different and
represent a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, hydrogen atom or halogen atom;
pyrone compounds represented by formula (1) in which R1 , R3 and R4 represent a hydrogen atom; pyrone compounds represented by formula (1) in which R1 , R3 , R4 and R5 represent a hydrogen atom;
pyrone compounds represented by formula (1) in which Q1 represents an oxygen atom,
R1 , R3 , R4 and R5 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, hydrogen atom or halogen atom;
pyrone compounds represented by formula (1) in which Q1 represents an oxygen atom,
R1 , R3 , R4 and R5 represent a hydrogen atom; pyrone compounds represented by formula (1) in which R2 represents a C1-C6 chain hydrocarbon optionally substituted by at least one halogen atom, phenyl group optionally substituted by at least one member selected from Group X, hydrogen atom, halogen atom, nitro group, cyano group or -L1 R9 ;
pyrone compounds represented by formula (1) in which R2 represents a phenyl group optionally substituted by at least one member selected from Group X, hydrogen atom or halogen atom;
pyrone compounds represented by formula (1) in which R2 represents a hydrogen atom or halogen atom;
pyrone compounds represented by formula (1) in which
R2 represents a hydrogen atom;
pyrone compounds represented by formula (1) in which Q1 represents an oxygen atom,
R2 represents a phenyl group optionally substituted by at least one member selected from Group X, hydrogen atom or halogen atom;
pyrone compounds represented by formula (1) in which Q1 represents an oxygen atom,
R2 represents a hydrogen atom or halogen atom;
pyrone compounds represented by formula (1) in which Q1 represents an oxygen atom,
R2 represents a hydrogen atom;
pyrone compounds represented by formula (1) in which R1 , R3 , R4 and R5 represent a hydrogen atom, R2
represents a hydrogen atom or halogen atom, R6
represents a hydrogen atom, halogen atom or -L2 R12 ;
pyrone compounds represented by formula (1) in which R1 , R , R3 , R4 , R5 and R6 represent a hydrogen atom; pyrone compounds represented by formula (1) in which R6 represents a hydrogen atom, halogen atom, cyano group or -L2 R12 ;
pyrone compounds represented by formula (1) in which R6 represents a hydrogen atom, halogen atom or -L2 R12 ; pyrone compounds represented by formula (1) in which L2 represents an oxygen atompyrone compound;
pyrone compounds represented by formula (1) in which L2 represents -NR13-;
pyrone compounds represented by formula (1) in which L2 represents -S(0)m-;
pyrone compounds represented by formula (1) in which R6 represents a hydrogen atom, halogen atom or -L2 R12 , L2 represents -NR13 - or S(0)m-, m represents 0,
R12 and R13 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, or hydrogen atom,
alternatively, R12 and R13 may be bound to form a 5- membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected;
pyrone compounds represented by formula (1) in which R6 represents a hydrogen atom, halogen atom or -L2 R12 , L2 represents -NR13 - or S(0)m-,
m represents 0,
R12 and R13 are the same or different and represent a C1-C4 chain hydrocarbon group optionally substituted by a hydrogen atom, cyclopropyl group, cyclopropylmethyl group or hydrogen atom;
pyrone compounds represented by formula (1) in which R6 represents a hydrogen atom or halogen atom;
pyrone compounds represented by formula (1) in which R6 represents a hydrogen atom; pyrone compounds represented by formula (1) in which Q1 represents an oxygen atom,
R6 represents a hydrogen atom, halogen atom or - L2 R12 ;
pyrone compounds represented by formula (1) in which Q1 represents an oxygen atom, R6 represents a hydrogen atom, halogen atom or - L2 R12 , L2 represents -NR13 - or S(0)m-, m represents 0,
R12 and R13 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, or hydrogen atom,
alternatively, R12 and R13 may be bound to form a 5- membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected;
pyrone compounds represented by formula (1) in which Q1 represents an oxygen atom,
R6 represents a hydrogen atom, halogen atom or - L2 R12 , L2 represents -NR13 - or S(0)m-, m represents 0,
R12 and R13 are the same or different and represent a C1-C4 chain hydrocarbon group optionally substituted by at least one halogen atom, cyclopropyl group,
cyclopropylmethyl group or hydrogen atom;
pyrone compounds represented by formula (1) in which
Q1 represents an oxygen atom,
R6 represents a hydrogen atom or halogen atom;
pyrone compounds represented by formula (1) in which Q1 represents an oxygen atom,
R6 represents a hydrogen atom;
pyrone compounds represented by formula (1) in which Q1 represents an oxygen atom,
R1 , R3 , R4 and R5 represent a hydrogen atom,
R2 represents a hydrogen atom or halogen atom, R6 represents a hydrogen atom, halogen atom or - L2 R12 , L2 represents -NR13 - or S(0)m-, m represents 0,
R12 and R13 are the same or different and represent a C1-C4 chain hydrocarbon group optionally substituted by at least one halogen atom, cyclopropyl group,
cyclopropylmethyl group or hydrogen atom;
pyrone compounds represented by formula (1) in which Q1 represents an oxygen atom,
R1 , R2 , R3 , R4 and R5 represent a hydrogen atom, R6 represents a hydrogen atom or halogen atom;
pyrone compounds represented by formula (1) in which Q1 represents an oxygen atom,
R1 , R , R3 , R4 , R5 and R6 represent a hydrogen atom; pyrone compounds represented by formula (1) in which R7 and R8 are the same or different and represent a Cl- C3 chain hydrocarbon group optionally substituted by at least one member selected from Group , hydrogen atom, or -L3 R1 , alternatively, R7 and R8 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected; pyrone compounds represented by formula (1) in which
Q3 represents an oxygen atom;
pyrone compounds represented by formula (1) in which Q3 represents a sulfur atom;
pyrone compounds represented by formula (1) in which R1 represents a C1-C4 chain hydrocarbon group
optionally substituted by at least one member selected from Group W, C3-C6 alicyclic hydrocarbon group
optionally substituted by at least one member selected from Group a, phenyl group optionally substituted by at least one member selected from Group X, 5-membered heterocyclic group optionally substituted by at least one member selected from Group X, 6-membered
heterocyclic group optionally substituted by at least one member selected from Group X or -L4 R15 ;
pyrone compounds represented by formula (1) in which R14 represents a C1-C4 chain hydrocarbon group
optionally substituted by at least one member selected from Group W, C3-C6 alicyclic hydrocarbon group
optionally substituted by at least one member selected from Group a or -L4 R15 ;
pyrone compounds represented by formula (1) in which R1 represents a C1-C4 chain hydrocarbon group
optionally substituted by at least one member selected from Group Y, cyclopropyl group optionally substituted by at least one member selected from Group a or -L R15 ; pyrone compounds represented by formula (1) in which R15 represents a C1-C4 chain hydrocarbon group
optionally substituted by at least one member selected from Group W, C3-C6 alicyclic hydrocarbon group
optionally substituted by at least one member selected from Group a, 5-membered heterocyclic group optionally substituted by at least one member selected from Group X or 6-membered heterocyclic group optionally substituted by at least one member selected from Group X; pyrone compounds represented by formula (1) in which R15 represents a C1-C4 chain hydrocarbon group
optionally substituted by at least one member selected from Group W or C3-C6 alicyclic hydrocarbon group optionally substituted by at least one member selected from Group a;
pyrone compounds represented by formula (1) in which R15 represents a C1-C4 chain hydrocarbon group
optionally substituted by at least one member selected from Group Y, cyclopropylmethyl group or cyclopropyl group optionally substituted by at least one member selected from Group a;
pyrone compounds represented by formula (1) in which R16 represents a C1-C3 chain hydrocarbon group
optionally substituted by at least one member selected from Group Y, or hydrogen atom, alternatively, R16 and R15 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected;
pyrone compounds represented by formula (1) in which R16 represents a C1-C3 chain hydrocarbon group
optionally substituted by at least one member selected from Group Y, or hydrogen atom;
pyrone compounds represented by formula (1) in which R14 represents a methyl group, ethyl group, propyl group, isopropyl group, trifluoromethyl group,
cyclopropyl group or -L4 R15 ,
R15 represents a methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, benzyl group, trifluoroethyl group, cyclopropyl group, cyclopropylmethyl group, 2-propenyl group or 2-propynyl group,
R16 represents a methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, benzyl group, trifluoroethyl group, cyclopropyl group, cyclopropylmethyl group, 2-propenyl group, 2-propynyl group or hydrogen atom; pyrone compounds represented by formula (1) in which R7 and R8 are the same or different and represent a Cl- C3 chain hydrocarbon group optionally substituted by at least one member selected from Group W, hydrogen atom or -L3 R14 , alternatively, R7 and R8 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected,
R1 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group W, C3-C6 alicyclic hydrocarbon group
optionally substituted by at least one member selected from Group a, 5-membered heterocyclic group optionally substituted by at least one member selected from Group X, 6-membered heterocyclic group optionally substituted by at least one member selected from Group X or -L R15 ,
R15 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group , C3-C6 alicyclic hydrocarbon group
optionally substituted by at least one member selected from Group a, phenyl group optionally substituted by at least one member selected from Group X, 5-membered heterocyclic group optionally substituted by at least one member selected from Group X or 6-membered
heterocyclic group optionally substituted by at least one member selected from Group X,
R16 represents a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, or hydrogen atom, alternatively, R16 and R15 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected;
pyrone compounds represented by formula (1) in which Q1 represents an oxygen atom,
R7 and R8 are the same or different and represent a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group W, hydrogen atom, or -L3 R1 , alternatively, R7 and R8 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected,
R14 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group , C3-C6 alicyclic hydrocarbon group
optionally substituted by at least one member selected from Group a, 5-membered heterocyclic group optionally substituted by at least one member selected from Group X, 6-membered heterocyclic group optionally substituted by at least one member selected from Group X or -L4 R15 ,
R15 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group W, C3-C6 alicyclic hydrocarbon group
optionally substituted by at least one member selected from Group a, 5-membered heterocyclic group optionally substituted by at least one member selected from Group X or 6-membered heterocyclic group optionally substituted by at least one member selected from Group X,
R16 represents a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, or hydrogen atom, alternatively, R16 and R15 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected;
pyrone compounds represented by formula (1) in which Q1 represents an oxygen atom,
Q3 represents an oxygen atom,
R7 and R8 are the same or different and represent a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group W, hydrogen atom or -L3R14, alternatively, R7 and R8 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected,
R14 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group W, C3-C6 alicyclic hydrocarbon group
optionally substituted by at least one member selected from Group a, 5-membered heterocyclic group optionally substituted by at least one member selected from Group X, 6-membered heterocyclic group optionally substituted by at least one member selected from Group X or -L4 R15 , R15 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group , C3-C6 alicyclic hydrocarbon group
optionally substituted by at least one member selected from Group a, 5-membered heterocyclic group optionally substituted by at least one member selected from Group X or 6-membered heterocyclic group optionally substituted by at least one member selected from Group X,
R16 represents a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, or hydrogen atom, alternatively, R16 and R15 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected; pyrone compounds represented by formula (1) in which R7 and R8 are the same or different and represent a Cl- C3 chain hydrocarbon group optionally substituted by at least one member selected from Group , hydrogen atom or -L3 R14 , alternatively, R7 and R8 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected,
R14 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group W, C3-C6 alicyclic hydrocarbon group
optionally substituted by at least one member selected from Group a or -L4 R15 ,
R15 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group W or C3-C6 alicyclic hydrocarbon group optionally substituted by at least one member selected from Group a,
R16 represents a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y or hydrogen atom;
pyrone compounds represented by formula (1) in which Q1 represents an oxygen atom,
R7 and R8 are the same or different and represent a
C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group W, hydrogen atom or -L3 R1 , alternatively, R7 and R8 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected,
R14 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group , C3-C6 alicyclic hydrocarbon group
optionally substituted by at least one member selected from Group a or -L4 R15 ,
R15 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group W or C3-C6 alicyclic hydrocarbon group optionally substituted by at least one member selected from Group a,
R16 represents a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y or hydrogen atom;
pyrone compounds represented by formula (1) in which Q1 represents an oxygen atom,
Q3 represents an oxygen atom, R7 and R8 are the same or different and represent a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group , hydrogen atom or -L3R1 , alternatively, R7 and R8 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected,
R1 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group W, C3-C6 alicyclic hydrocarbon group
optionally substituted by at least one member selected from Group a or -L4 R15 ,
R15 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group or C3-C6 alicyclic hydrocarbon group optionally substituted by at least one member selected from Group a,
R16 represents a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y or hydrogen atom;
pyrone compounds represented by formula (1) in which Q1 represents an oxygen atom,
Q3 represents an oxygen atom,
R7 and R8 are the same or different and represent a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group W, hydrogen atom or -L3R14, alternatively, R7 and R8 may be bound to form a 5-meitibered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected,
R14 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, C3-C6 alicyclic hydrocarbon group
optionally substituted by at least one member selected from Group a or -L4 R15 ,
R1 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group W or C3-C6 alicyclic hydrocarbon group optionally substituted by at least one member selected from Group a,
R16 represents a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y or hydrogen atom;
pyrone compounds represented by formula (1) in which Q1 represents an oxygen atom,
Q3 represents an oxygen atom,
R7 and R8 are the same or different and represent a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, hydrogen atom or -L3^ ,
R14 represents a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, cyclopropyl group optionally substituted by at least one member selected from Group a or -L4 R15 , R15 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group W or cyclopropyl group optionally substituted by at least one member selected from Group a,
R16 represents a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y or hydrogen atom; pyrone compounds represented by formula (1) in which Q1 represents an oxygen atom,
Q3 represents an oxygen atom,
R7 and R8 are the same or different and represent a methyl group, ethyl group, methoxymethyl group,
ethoxymethyl group, benzyloxymethyl group, hydrogen atom or -L3 R14 ,
R14 represents a methyl group, ethyl group, propyl group, isopropyl group, trifluoromethyl group,
cyclopropyl group or -L4 R15 ,
R15 represents a methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, benzyl group, tri fluoroethyl group, cyclopropyl group, cyclopropylmethyl group, 2-propenyl group or 2-propynyl group ,
R16 represents a methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, benzyl group, trifluoroethyl group, cyclopropyl group, cyclopropylmethyl group, 2-propenyl group, 2-propynyl group or hydrogen atom; pyrone compounds represented by formula (1) in which
Q1 represents an oxygen atom,
R1 , R3 , R4 and R5 represent a hydrogen atom,
R2 represents a hydrogen atom or halogen atom,
R6 represents a hydrogen atom, halogen atom or -
L2 R12 ,
L2 represents -NR13 - or S(0)m-, m represents 0, R12 and R13 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, or hydrogen atom,
alternatively, R12 and R13 may be bound to form a 5- membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6^membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected,
R7 and R8 are the same or different and represent a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group W, hydrogen atom or -L3R14, alternatively, R7 and R8 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected,
R14 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group W, C3-C6 alicyclic hydrocarbon group
optionally substituted by at least one member selected from Group a or -L4 R15 ,
R15 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group W or C3-C6 alicyclic hydrocarbon group optionally substituted by at least one member selected from Group a,
R16 represents a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y or hydrogen atom; pyrone compounds represented by formula (1) in which Q1 represents an oxygen atom,
R1 , R3 , R4 and R5 represent a hydrogen atom,
R2 represents a hydrogen atom or halogen atom,
R6 represents a hydrogen atom, halogen atom or -
L2 R12 ,
L2 represents -NR13 - or S(0)m-, m represents 0,
R1 and R1 are the same or different and represent a C1-C4 chain hydrocarbon group optionally substituted by a hydrogen atom, cyclopropyl group, cyclopropylmethyl group or hydrogen atom,
R7 and R8 are the same or different and represent a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, hydrogen atom or -L3 R1 ,
R14 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, cyclopropyl group optionally substituted by at least one member selected from Group . or -L4 R15 , R15 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, cyclopropylmethyl group or cyclopropyl group optionally substituted by at least one member selected from Group a,
R16 represents a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y or hydrogen atom; pyrone compounds represented by formula (1) in which
Q1 represents an oxygen atom,
pyrone compounds represented by formula (1) in which Q1 represents an oxygen atom,
R7 and R8 are the same or different and represent a hydrogen atom;
Q3 represents an oxygen atom,
R1 , R2 , R3 , R4 , R5 and R6 represent a hydrogen atom, R7 and R8 are the same or different and represent a methyl group, ethyl group, methoxymethyl group,
ethoxymethyl group, benzyloxymethyl group, hydrogen atom or -L3 R1 ,
R1 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, cyclopropyl group optionally substituted by at least one member selected from Group a or -L4 R15 ,
R15 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, cyclopropylmethyl group or cyclopropyl group optionally substituted by at least one member selected from Group a,
R16 represents a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y or hydrogen atom; pyrone compounds represented by formula (1) in which Q1 represents an oxygen atom,
Q3 represents an oxygen atom,
R1 , R2 , R3 , R4 , R5 and R6 represent a hydrogen atom, R7 and R8 are the same or different and represent a methyl group, ethyl group, methoxymethyl group,
ethoxymethyl group, benzyloxymethyl group, hydrogen atom or -L3 R14 ,
R14 represents a methyl group, ethyl group, propyl group, isopropyl group, trifluoromethyl group,
cyclopropyl group or -L4 R15 ,
R15 represents a methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, benzyl group, trifluoroethyl group, cyclopropyl group, cyclopropylmethyl group, 2-propenyl group or 2-propynyl group,
R16 represents a methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, benzyl group, trifluoroethyl group, cyclopropyl group, cyclopropylmethyl group, 2-propenyl group, 2-propynyl group or hydrogen atom; pyrone compounds represented by formula (1) in which represents an oxygen atom, R7 and R8 are the same or different and represent a hydrogen atom; pyrone compounds represented by formula (1) in which Q1 represents an oxygen atom,
R7 and R8 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted by at least one member selected from Group Y; pyrone compounds represented by formula (1) in which Q1 represents an oxygen atom,
R7 and R8 are the same or different and represent - C (=0) R1 ; pyrone compounds represented by formula (1) in which Q1 represents an oxygen atom,
R7 and R8 are the same or different and represent - C (=0) R14 ,
R14 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group Y or C3-C6 alicyclic hydrocarbon group optionally substituted by at least one member selected from Group Y; pyrone compounds represented by formula (1) in which Q1 represents an oxygen atom,
R7 and R8 are the same or different and represent - S(0)2R1 ; pyrone compounds represented by formula (1) in which Q1 represents an oxygen atom,
R7 and R8 are the same or different and represent - C(=0)OR15; pyrone compounds represented by formula (1) in which Q1 represents an oxygen atom,
R7 and R8 are the same or different and represent - C (=0) NR15 R16 ; pyrone compounds represented by formula (1) in which
Q1 represents an oxygen atom,
R1 , R2 , R3 , R , R5 and R6 represent a hydrogen atom, R7 and R8 are the same or different and represent a hydrogen atom; pyrone compounds represented by formula (1) in which
Q1 represents an oxygen atom,
R1 , R2 , R3 , R4 , R5 and R6 represent a hydrogen atom, R7 and R8 are the same or different and represent a
C1-C6 chain hydrocarbon group optionally substituted by at least one member selected from Group Y; pyrone compounds represented by formula (1) in which
Q1 represents an oxygen atom,
R1 , R2 , R3 , R4 , R5 and R6 represent a hydrogen atom, R7 and R8 are the same or different and represent -
C(=0)R14,
R14 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group Y or C3-C6 alicyclic hydrocarbon group optionally substituted by at least one member selected from Group Y; pyrone compounds represented by formula (1) in which
Q1 represents an oxygen atom,
R1 , R2 , R3 , R4 , R5 and R6 represent a hydrogen atom, R7 and R8 are the same or different and represent -
C(=0)R14; pyrone compounds represented by formula (1) in which
Q1 represents an oxygen atom,
R1 , R2 , R3 , R , R5 and R6 represent a hydrogen atom, R7 and R8 are the same or different and represent -
S(0)2R14 ; pyrone compounds represented by formula (1) in which
Q1 represents an oxygen atom,
R1 , R2 , R3 , R4 , R5 and R6 represent a hydrogen atom, R7 and R8 are the same or different and represent -
C (=0) OR15 ; pyrone compounds represented by formula (1) in which
Q1 represents an oxygen atom,
R1 , R2 , R3 , R4 , R5 and R6 represent a hydrogen atom, R7 and R8 are the same or different and represent -
C (=0) NR15 R16 ; pyrone compounds represented by formula (1) in which Q1 represents an oxygen atom,
R7 represents -C(=0)R14, -S(0)2R14, -C(=0)OR1 or - C (=0) R15 R16 ,
R8 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, -C(=0)R14, -C(=0)0R15 or hydrogen atom; pyrone compounds represented by formula (1) in which Q1 represents an oxygen atom,
R7 represents -C(=0)R1 , -S(0)2R14, -C(=0)OR15 or - C (=0) NR15 R16 ,
R8 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, -C(=0)R14, -C(=0)OR1 or hydrogen atom, R14 represents C1-C6 chain hydrocarbon group
optionally substituted by at least one member selected from Group Y or C3-C6 alicyclic hydrocarbon group optionally substituted by at least one member selected from Group Y,
R15 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group Y,
R16 represents a C1-C5 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, C3-C6 alicyclic hydrocarbon group
optionally substituted by at least one member selected from Group Y or hydrogen atom; pyrone compounds represented by formula (1) in which Q1 represents an oxygen atom,
R7 represents -C(=0)R14, -S(0)2R14, -C(=0)OR15 or - C (=0) NR15 R16 ,
R8 represents a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, -C(=0)R14, -C(=0)0R15 or hydrogen atom,
R14 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group Y or cyclopropyl group optionally substituted by at least one member selected from Group Y,
R15 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group Y,
R16 represents a C1-C5 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, C3-C6 alicyclic hydrocarbon group
optionally substituted by at least one member selected from Group Y or hydrogen atom; pyrone compounds represented by formula (1) in which Q1 represents an oxygen atom,
R7 represents -C(=0)R14, -S(0)2R14, -C(=0)OR15 or - C (=0) NR15 R16 ,
R8 represents a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, -C(=0)R14, -C(=0)0R15 or hydrogen atom, R14 represents a C1-C3 chain hydrocarbon group or cyclopropyl group, R15 represents a C1-C3 chain hydrocarbon group, R16 represents a C1-C5 chain hydrocarbon group, cyclopropyl group or hydrogen atom; pyrone compounds represented by formula (1) in which
Q1 represents an oxygen atom,
R1 , R3 , R4 and R5 represent a hydrogen atom,
R2 represents a hydrogen atom or halogen atom,
R6 represents a hydrogen atom, halogen atom or -
L2 R12 ,
L2 represents -NR13 - or S(0)m-, m represents 0,
R12 and R13 are the same or different and represent a C1-C4 chain hydrocarbon group optionally substituted by a hydrogen atom, cyclopropyl group, cyclopropylmethyl group or hydrogen atom,
R7 represents -C(=0)R14, -S(0)2R14, -C(=0)OR15 or - C (=0) NR15 R16 ,
R8 represents a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, -C(=0)R1 , -C(=0)OR15 or hydrogen atom,
R14 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group Y or cyclopropyl group optionally substituted by at least one member selected from Group Y,
R15 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group Y,
R16 represents a C1-C5 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, C3-C6 alicyclic hydrocarbon group
optionally substituted by at least one member selected from Group Y or hydrogen atom; pyrone compounds represented by formula (1) in which
Q1 represents an oxygen atom,
R1 , R3 , R4 and R5 represent a hydrogen atom,
R2 represents a hydrogen atom or halogen atom,
R6 represents a hydrogen atom, halogen atom or - L2 R12 ,
L2 represents -NR13 - or S(0)m-, m represents 0,
R12 and R13 are the same or different and represent a C1-C4 chain hydrocarbon group optionally substituted by a hydrogen atom, cyclopropyl group, cyclopropylmethyl group or hydrogen atom,
R7 represents -C(=0)R14, -S(0)2R14, -C(=0)OR15 or - C (=0) NR15 R16 ,
R8 ¾C1-C3 chain hydrocarbon group optionally
substituted by at least one member selected from Group Y, -C(=0)R14, -C(=0)OR15 or hydrogen atom,
R1 represents a C1-C3 chain hydrocarbon group or cyclopropyl group,
R15 represents a C1-C3 chain hydrocarbon group,
R16 represents a C1-C5 chain hydrocarbon group, cyclopropyl group or hydrogen atom; pyrone compounds represented by formula (1) in which Q1 represents an oxygen atom,
R1 , R2 , R3 , R4 , R5 and R6 represent a hydrogen atom, R7 represents -C(=0)R14, -S(0)2R14, -C(=0)OR15 or - C (=0) NR15 R16 ,
R8 represents a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, -C(=0)R14, -C(=0)OR15 or hydrogen atom,
R1 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group Y or cyclopropyl group optionally substituted by at least one member selected from Group Y,
R15 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group Y,
R16 represents a C1-C5 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, C3-C6 alicyclic hydrocarbon group
optionally substituted by at least one member selected from Group Y or hydrogen atom; pyrone compounds represented by formula (1) in which Q1 represents an oxygen atom,
R1 , R2 , R3 , R4 , R5 and R6 represent a hydrogen atom,
R7 represents -C(=0)R14, -S(0)2R14, -C(=0)OR15 or - C (=0) NR15 R16 ,
R8 represents a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, -C(=0)R14, -C(=0)0R15 or hydrogen atom,
R14 represents a C1-C3 chain hydrocarbon group or cyclopropyl group,
R15 represents a C1-C3 chain hydrocarbon group, R16 represents a C1-C5 chain hydrocarbon group, cyclopropyl group or hydrogen atom; pyrone compounds represented by formula (1) in which Q1 represents an oxygen atom,
R1 , R2 , R3 , R4 , R5 and R6 represent a hydrogen atom,
R7 represents -C(=0)R14, -C(=0)OR15 or - C (=0) NR15 R16 ,
R8 represents a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, -C(=0)R1 , -C(=0)0R15 or hydrogen atom,
R1 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group Y or cyclopropyl group optionally substituted by at least one member selected from Group Y,
R15 represents a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group Y,
R16 represents a C1-C5 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, C3-C6 alicyclic hydrocarbon group
optionally substituted by at least one member selected from Group Y or hydrogen atom; pyrone compounds represented by formula (1) in which
Q1 represents an oxygen atom,
R1 , R2 , R3 , R4 , R5 and R6 represent a hydrogen atom, R7 represents -C(=0)R14, -C(=0)0R15 or -
C (=0) NR15 R16 , R represents a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, -C(=0)R14, -C(=0)OR15 or hydrogen atom,
R14 represents a C1-C3 chain hydrocarbon group or cyclopropyl group,
R15 represents a C1-C3 chain hydrocarbon group,
R16 represents a C1-C5 chain hydrocarbon group, cyclopropyl group or hydrogen atom;
Next, the method of producing an inventive compound is described.
The inventive compound can be produced, for example, by the following (Production Method 1) to (Production Method 17) .
(Production Method 1)
Among inventive compounds, a compound (4-a) in which n represents 0, Q1 represents an oxygen atom, R7
represents -C(=0)R1 and R8 represents a hydrogen atom can be produced by reacting a compound (2) and a
compound ( 3 ) .
Figure imgf000071_0001
Figure imgf000071_0002
(4 - a) (4 - P)
[wherein, R1 , R2 , R3 , R , R5 , R6 and R14 represent the same meaning as described above.]
In the reaction, acetic anhydride is usually used as a solvent, and a mixed solvent with other solvents may also be used.
Examples of the other solvents to be used in the reaction include ethers such as tetrahydrofuran
(hereinafter, referred to as THF in some cases),
ethylene glycol dimethyl ether, 1,4-dioxane and the like, aromatic hydrocarbons such as toluene, xylene and the like, halogenated hydrocarbons such as
chlorobenzene , dichlorobenzene and the like, fatty acids such as acetic acid and the like and mixtures thereof.
The compound (3) is used usually in a proportion of 1 to 3 mol with respect to 1 mol of the compound (2) .
The reaction temperature of the reaction is usually in the range of 50 to 200°C, and the reaction time thereof is usually in the range of 0.1 to 24 hours.
In the case of use of acetic anhydride as a solvent, a compound (4-p) is obtained in some cases. After completion of the reaction, the compound (4-a) and / or (4-p) can be isolated by performing post treatment operations such as, for example, cooling of the reaction mixture to room temperature, addition of ethanol or the like if necessary, and filtration of the deposited precipitate, drying thereof and the like. As another method, it is also possible to distill off the solvent and to perform purification thereof by
chromatography, after completion of the reaction. The isolated compound (4-a) and/or (4-p) can also be further purified by chromatography, re-crystallization and the like .
(Production Method 2)
Among inventive compounds, a compound (5) in which n represents 0, Q1 represents an oxygen atom and R7 and R8 represent a hydrogen atom can be produced by reacting a compound (4-a-a) with a Lewis acid, then, treating this with a basic solution.
Figure imgf000072_0001
(4 - a - a) (5)
[wherein, R1 , R2 , R3 , R4 , R5 and R6 represent the same meaning as described above.]
The reaction is carried out usually in the presence of a solvent. Examples of the solvent to be used in the reaction include THF, alcohols such as methanol, ethanol and the like, ethers such as ethylene glycol dimethyl ether, 1,4-dioxane and the like, toluene, aromatic hydrocarbons such as xylene and the like, halogenated hydrocarbons such as dichloromethane , chloroform, chlorobenzene , dichlorobenzene and the like and mixtures thereof.
Examples of the Lewis acid to be used in the
reaction include boron halides such as boron
trifluoride-methanol and the like, etc.
Examples of the basic solution to be used include aqueous solutions of alkali metal carbonates such as a sodium carbonate aqueous solution, sodium hydrogen carbonate aqueous solution, potassium carbonate aqueous solution, potassium hydrogen carbonate aqueous solution and the like.
The Lewis acid is used usually in a proportion of 1 to 10 mol and the base in the basic solution is used usually in a proportion of 1 to 20 mol with respect to 1 mol of the compound (4-a-a) .
The reaction temperature in the process of reacting the compound (4-a-a) with the Lewis acid is usually in the range of 10 to 100°C, and the reaction time thereof is in the range of 0.1 to 24 hours.
After completion of the reaction of the compound (4- a-a) with the Lewis acid, the reaction mixture is cooled to room temperature, the deposited precipitate is filtrated, and the resultant precipitate can be used as it is in a process of treating with a basic solution. The treatment temperature in the process of treating with a basic solution is usually in the range of 0 to 25°C, and the treatment time thereof is usually in the range of 0.1 to 2 hours.
After treatment with a basic solution, the compound (5) can be isolated by performing post treatments such as filtration of the deposited precipitate, drying thereof and the like. The isolated compound (5) can also be further purified by chromatography, re- crystallization and the like.
(Production Method 3)
Among inventive compounds, a compound (4) in which n represents 0, Q1 represents an oxygen atom, R7
represents -L3 R14 and R8 represents a hydrogen atom can be produced by reacting a compound (5) with an acid chloride represented by formula (6) (hereinafter, referred to as a compound (6)) or an acid anhydride represented by formula (7) (hereinafter, referred to as a compound (7)) in the presence of a base.
Figure imgf000074_0001
[wherein, R1 , R2 , R3 , R4 , R5 , R6 , R14 and L3 represent the same meaning as described above.]
The reaction is carried out usually in the presence of a solvent, however, the reaction may also be carried out in the absence of a solvent.
Examples of the solvent to be used in the reaction include THF, nitriles such as acetonitrile and the like, acid amides such as N , N-dimethylformamide (hereinafter, referred to as, DMF in some cases), N-methyl-2 - pyrrolidinone (hereinafter, referred to as, NMP in some cases) and the like, sulfoxides such as dimethyl
sulfoxide (hereinafter, referred to as, DMSO in some cases) and the like, ethers such as ethylene glycol dimethyl ether, 1,4-dioxane and the like, aromatic hydrocarbons such as toluene, xylene and the like, halogenated hydrocarbons such as dichloromethane , chloroform, chlorobenzene , dichlorobenzene and the like and mixtures thereof.
Examples of the base to be used in the reaction include alkali metal carbonates such as sodium
carbonate, potassium carbonate and the like, tertiary amines such as triethylamine, diisopropylethylamine and the like, nitrogen-containing aromatic hydrocarbons such as pyridine, 4 -dimethylaminopyridine and the like, etc.
The compound (6) or compound (7) is used usually in a proportion of 1 to 10 mol and the base is used usually in a proportion of 1 to 10 mol with respect to 1 mol of the compound (5) .
The reaction temperature of the reaction is usually in the range of 0 to 100°C, and the reaction time thereof is in the range of 0.5 to 24 hours.
After completion of the reaction, a compound (4) can be isolated by performing post treatment operations such as extraction of the reaction mixture with an organic solvent, drying of the organic layer, concentration thereof and the like.
The compound (4) can be isolated by performing operations such as distillation off of the solvent, addition of water, filtration of the precipitate, drying thereof and the like, after completion of the reaction, as other post treatment operations. The isolated compound (4) can also be further purified by
chromatography, re-crystallization and the like.
(Production Method 4)
Among inventive compounds, a compound (4-a-b) in which n represents 0, Q1 represents an oxygen atom, R7 represents -C (=Q3 ) NHR15 and R8 represents a hydrogen atom can be produced by reacting a compound (5) with a compound ( 8 ) .
Figure imgf000076_0001
(5) (4-a-b)
[wherein, R1 , R2 , R3 , R4 , R5 , R6 , R15 and Q3 represent the same meaning as described above.]
The reaction may be carried out in the absence of a solvent, or may be carried out using a solvent.
Examples of the solvent to be used in the reaction include THF, nitriles such as acetonitrile and the like, acid amides such as DMF, N P and the like, ethers such as ethylene glycol dimethyl ether, 1,4-dioxane and the like, aromatic hydrocarbons such as toluene, xylene and the like, halogenated hydrocarbons such as
dichloromethane , chloroform, chlorobenzene ,
dichlorobenzene and the like, esters such as ethyl acetate, butyl acetate and the like and mixtures
thereof .
The compound (8) is used usually in a proportion of 1 to 100 mol with respect to 1 mol of the compound (5) .
The reaction temperature of the reaction is usually in the range of 0 to 200°C, and the reaction time thereof is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the compound (4-a- b) can be isolated by performing operations such as cooling of the reaction mixture to room temperature, filtration of the deposited precipitate, drying thereof and the like. The isolated compound (4-a-b) can also be further purified by chromatography, re-crystallization and the like.
(Production Method 5)
Among inventive compounds, a compound (9) in which n represents 0, Q1 represents an oxygen atom, and R7 and R8 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected can be produced by reacting a compound (4-b) in the resence of a base.
Figure imgf000078_0001
[wherein, R1 , R2 , R3 , R4 , R5 , R6 and L3 represent the same meaning as described above, L 4 x represents a methylene group optionally substituted by at least one member selected from Group Y or -L4 , A4 represents a methylene group optionally substituted by at least one member selected from Group Y, p represents 2 or 3, E represents a leaving group such as a chlorine atom, bromine atom or iodine atom and the like.]
The reaction is carried out usually in the presence of a solvent.
Examples of the solvent to be used in the reaction include THF, nitriles such as acetonitrile and the like, acid amides such as D F, NMP and the like, sulfoxides such as DMSO and the like, ethers such as ethylene glycol dimethyl ether, 1,4-dioxane and the like,
aromatic hydrocarbons such as toluene, xylene and the like, halogenated hydrocarbons such as dichloromethane , chloroform, chlorobenzene , dichlorobenzene and the like and mixtures thereof.
Examples of the base to be used in the reaction include alkali metal hydrides such as sodium hydride, potassium hydride and the like, alkali metal alkoxides such as sodium tert-butoxide, potassium tert-butoxide and the like, etc.
The base is used usually in a proportion of 1 to 10 mol with respect to 1 mol of the compound (4-b) .
The reaction temperature of the reaction is usually in the range of 0 to 100°C, and the reaction time thereof is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (9) can be isolated by performing post treatment operations such as extraction of the reaction mixture with an organic solvent, drying of the organic layer,
concentration thereof and the like. The isolated
compound (9) can also be further purified by
chromatography, re-crystallization and the like.
(Production Method 6)
Among inventive compounds, a compound (10) in which n represents 0, Q1 represents an oxygen atom, Q3
represents an oxygen atom, and R7 and R8 may be bound to form a 5-membered heterocyclic ring optionally
substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected can be produced by reacting a compound (4-c) in the presence of a base in an acid anhydride.
Figure imgf000080_0001
[wherein, R1 , R2 , R3 , R4 , R5 , R6 , L4X and A4 represent the same meaning as described above, q represents 1 or 2. ]
The reaction is carried out usually using, as a solvent, acid anhydrides such as acetic anhydride, propionic anhydride and the like, however, other
solvents may also be mixed.
Examples of the other solvents to be used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, 1,4-dioxane and the like, aromatic hydrocarbons such as toluene, xylene and the like, halogenated hydrocarbons such as dichloromethane, chloroform, chlorobenzene , dichlorobenzene and the like, esters such as ethyl acetate, butyl acetate and the like and mixtures thereof.
The base to be used in the reaction includes fatty acid alkali metal salts such as sodium acetate,
potassium acetate and the like.
The base is used usually in a proportion of 0.01 to 2 mol with respect to 1 mol of the compound (4-c).
The reaction temperature of the reaction is usually in the range of 10 to 200°C, and the reaction time thereof is usually in the range of 0.5 to 24 hours. After completion of the reaction, the compound (10) can be isolated by performing post treatments such as distillation off of the solvent, neutralization of the reaction mixture with a basic aqueous solution such as a sodium carbonate aqueous solution and the like,
filtration of the deposited precipitate and the like. The isolated compound (10) can also be further purified by chromatography, re-crystallization and the like.
(Production Method 7)
Among inventive compounds, a compound (12) in which n represents 0, Q1 represents an oxygen atom and R7 represents -L3R14 can be produced by reacting a compound (4) with a compound (11) in the presence of a base.
Figure imgf000081_0001
[wherein, R1 , R2 , R3 , R4 , R5 , R6 , R7 , R8 , R14 , L3 and E represent the same meaning as described above.]
The reaction is carried out usually in the presence of a solvent .
Examples of the solvent to be used in the reaction include THF, nitriles such as acetonitrile and the like, acid amides such as DMF, NMP and the like, sulfoxides such as DMSO and the like, ethers such as ethylene glycol dimethyl ether, 1,4-dioxane and the like, aromatic hydrocarbons such as toluene, xylene and the like, halogenated hydrocarbons such as dichloromethane , chloroform, chlorobenzene , dichlorobenzene and the like and mixtures thereof.
Examples of the base to be used in the reaction include alkali metal hydrides such as sodium hydride, potassium hydride and the like, alkali metal alkoxides such as sodium tert-butoxide, potassium tert-butoxide and the like, etc.
The compound (11) is used usually in a proportion of
1 to 10 mol and the base is used usually in a proportion of 1 to 10 mol with respect to 1 mol of the compound (4) .
The reaction temperature of the reaction is usually in the range of 0 to 100°C, and the reaction time thereof is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the compound (12) can be isolated by performing post treatment operations such as extraction of the reaction mixture with an organic solvent, drying of the organic layer,
concentration thereof and the like. The isolated compound (12) can also be further purified by
chromatography, re-crystallization and the like. (Production Method 8)
Among inventive compounds, a compound (12-a) in which n represents 0, Q1 represents an oxygen atom and R7 and R8 represent -S(0)2R14 can be produced by
reacting a compound (5) with a compound (13) in the presence of a base.
Figure imgf000083_0001
[wherein, R1 , R2 , R3 , R4 , R5 , R6 and R1 represent the same meaning as described above.]
The reaction is carried out usually in the presence of a solvent.
Examples of the solvent to be used in the reaction include THF, nitriles such as acetonitrile and the like, acid amides such as DMF, NMP and the like, sulfoxides such as DMSO and the like, ethers such as ethylene glycol dimethyl ether, 1,4-dioxane and the like,
aromatic hydrocarbons such as toluene, xylene and the like, halogenated hydrocarbons such as dichloromethane , chloroform, chlorobenzene , dichlorobenzene and the like and mixtures thereof.
Examples of the base to be used in the reaction include alkali metal carbonates such as sodium
carbonate, potassium carbonate and the like, tertiary amines such as triethylamine , diisopropylethylamine and the like, nitrogen-containing aromatic hydrocarbons such as pyridine, 4-dimethylaminopyridine and the like, etc.
The compound (13) is used usually in a proportion of 1 to 10 mol and the base is used usually in a proportion of 1 to 10 mol with respect to 1 mol of the compound (5) .
The reaction temperature of the reaction is usually in the range of 0 to 100°C, and the reaction time thereof is in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (12- a) can be isolated by performing post treatment
operations such as extraction of the reaction mixture with an organic solvent, drying of the organic layer, concentration thereof and the like. The isolated compound (12-a) can also be further purified by
chromatography, re-crystallization and the like.
(Production Method 9)
Among inventive compounds, a compound (5-b) in which n represents 0, Q1 represents an oxygen atom, R6
represents a chlorine atom or bromine atom and R7 and R8 represent a hydrogen atom can be produced by reacting a compound (5-a) with a halogenation reagent.
Figure imgf000084_0001
(5 - a) (5 - b) [wherein, R1 , R2 , R3 , R4 and R5 represent the same meaning as described above, R6 " represents a chlorine atom or bromine atom. ]
The reaction is carried out usually in the presence of a solvent.
The solvent to be used in the reaction includes halogenated hydrocarbons such as dichloromethane , chloroform and the like, fatty acids such as acetic acid, propionic acid and the like and mixtures thereof.
The halogenation reagent to be used in the reaction includes chlorine, bromine, N-chlorosuccinimide
(hereinafter, referred to as NCS in some cases), N- bromosuccinimide (hereinafter, referred to as NBS in some cases) and the like.
The halogenation reagent is used usually in a proportion of 1 to 10 mol with respect to 1 mol of the compound ( 5-a ) .
The reaction temperature of the reaction is usually in the range of 0 to 100°C, and the reaction time thereof is in the range of 0.1 to 24 hours.
After completion of the reaction, a compound (5-b) can be isolated by performing post treatment operations such as neutralization of the reaction mixture with a basice solution such as, for example, a sodium carbonate aqueous solution and the like, extraction of the
reaction mixture with an organic solvent, drying of the organic layer, concentration thereof and the like.
Further, the compound (5-b) can be isolated by
performing post treatment operations such as filtration of the deposited precipitate, neutralization of the reaction mixture with a basic solution such as, for example, a sodium carbonate aqueous solution and the like, filtration of the precipitate, drying thereof and the like, after completion of the reaction, as other post treatment operation methods. The isolated compound (5-b) can also be further purified by chromatography, re-crystallization and the like.
(Production Method 10)
Among inventive compounds, a compound (12-b) in which n represents 0, Q1 represents an oxygen atom, R6 represents a chlorine atom or bromine atom and R7 and RE represent -C(=0)R1 can be produced by reacting a compound (5-b) with an acid chloride represented by formula 16) in the presence of a base.
Figure imgf000086_0001
[wherein, R1 , R2 , R3 , R4 , R5 , R6 ' b and R14 represent the same meaning as described above.]
In the case of use of pyridine as a base, the reaction is usually carried out in the absence of a solvent, however, the reaction may also be carried out using a solvent.
Examples of the solvent to be used in the reaction include THF, nitriles such as acetonitrile and the like, acid amides such as DMF, NMP and the like, sulfoxides such as DMSO and the like, ethers such as ethylene glycol dimethyl ether, 1,4-dioxane and the like,
aromatic hydrocarbons such as toluene, xylene and the like, halogenated hydrocarbons such as dichloromethane , chloroform, chlorobenzene, dichlorobenzene and the like and mixtures thereof.
Examples of the base to be used in the reaction include alkali metal carbonates such as sodium
carbonate, potassium carbonate and the like, tertiary amines such as triethylamine , diisopropylethylamine and the like, nitrogen-containing aromatic hydrocarbons such as pyridine, 4 -dimethylaminopyridine and the like, etc.
The compound (16) is used usually in a proportion of 1 to 10 mol and the base is used usually in a proportion of 2 to 100 mol with respect to 1 mol of the compound (5-b) .
The reaction temperature of the reaction is usually in the range of 0 to 100°C, and the reaction time thereof is in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (12- b) can be isolated by performing post treatment
operations such as distillation off of the solvent, extraction of the reaction mixture with an organic solvent, drying of the organic layer, concentration thereof and the like. The isolated compound (12-b) can also be further purified by chromatography, re- crystallization and the like.
(Production Method 11)
Among inventive compounds, a compound (4-d) in which n represents 0, Q1 represents an oxygen atom, R6
represents -NR12 R13 , R7 represents a hydrogen atom and R8 represents -C(=0)R14 can be produced by reacting a compound (12-b) with a compound (17).
Figure imgf000088_0001
[wherein, R1 , R2 , R3 , R4 , R5 , R6 " b , R12 , R13 and R1 represent the same meaning as described above.]
The reaction is carried out usually using a solvent, however, the reaction may also be carried out in the absence of a solvent.
Examples of the solvent to be used in the reaction include THF, alcohols such as methanol, ethanol and the like, nitriles such as acetonitrile and the like, acid amides such as DMF, N P and the like, ethers such as ethylene glycol dimethyl ether, 1,4-dioxane and the like, aromatic hydrocarbons such as toluene, xylene and the like, halogenated hydrocarbons such as
dichloromethane , chloroform, chlorobenzene ,
dichlorobenzene and the like, esters such as ethyl acetate, butyl acetate and the like and mixtures
thereof .
The compound (17) is used usually in a proportion of 1 to 10 mol with respect to 1 mol of the compound (12- b) .
The reaction temperature of the reaction is usually in the range of 0 to 100°C, and the reaction time thereof is in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (4-d) can be isolated by performing post treatment operations such as distillation off of the solvent, extraction of the reaction mixture with an organic solvent, drying of the organic layer, concentration thereof and the like. The isolated compound (4-d) can also be further purified by chromatography, re-crystallization and the like.
(Production Method 12)
Among inventive compounds, a compound (4-e) in which n represents 0, Q1 represents an oxygen atom, R6
represents -SR12, R7 represents a hydrogen atom and R8 represents -C(=0)R14 can be produced by reacting a compound (12-b) with a compound (18) in the presence of a base.
Figure imgf000089_0001
[wherein, R1 , R2 , R3 , R4 , R5 , R6_b, R 11J 2 and R14
represent the same meaning as described above.]
The reaction is carried out usually using a solvent, however, the reaction may also be carried out in the absence of a solvent.
Examples of the solvent to be used in the reaction include THF, alcohols such as methanol, ethanol and the like, nitriles such as acetonitrile and the like, acid amides such as DMF, NMP and the like, ethers such as ethylene glycol dimethyl ether, 1,4-dioxane and the like, aromatic hydrocarbons such as toluene, xylene and the like, halogenated hydrocarbons such as
dichloromethane , chloroform, chlorobenzene ,
dichlorobenzene and the like, esters such as ethyl acetate, butyl acetate and the like and mixtures
thereof.
Examples of the base to be used in the reaction include alkali metal hydrides such as sodium hydride, potassium hydride and the like, alkali metal carbonates such as sodium carbonate, potassium carbonate and the like, etc.
It is also possible that the compound (18) is reacted with an alkali metal hydride such as sodium hydride and the like to prepare an alkali metal salt thereof, then, it is used in the above-described
reaction.
The compound (18) is used usually in a proportion of 1 to 10 mol and the base is used usually in a proportion of 1 to 10 mol with respect to 1 mol of the compound (12-b) .
The reaction temperature of the reaction is usually in the range of 0 to 100°C, and the reaction time thereof is in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (4-e) can be isolated by performing post treatment operations such as distillation off of the solvent, extraction of the reaction mixture with an organic solvent, drying of the organic layer, concentration thereof and the like. The isolated compound (4-e) can also be further purified by chromatography, re-crystallization and the like. (Production Method 13)
Among inventive compounds, a compound (19) in which n represents 0, Q1 represents an oxygen atom and R7 represents a hydrogen atom can be produced by reacting a compound (12-c) in the presence of a Lewis acid, then, treating this with a basic solution.
Figure imgf000091_0001
(12-c) (19)
[wherein, R1 , R2 , R3 , R4 , R5 , R6 and R8 represent the same meaning as described above.]
The reaction is carried out usually in the presence of a solvent.
Examples of the solvent to be used in the reaction include THF, alcohols such as methanol, ethanol and the like, ethers such as ethylene glycol dimethyl ether, 1,4-dioxane and the like, aromatic hydrocarbons such as toluene, xylene and the like, halogenated hydrocarbons such as dichloromethane , chloroform, chlorobenzene , dichlorobenzene and the like and mixtures thereof.
Examples of the Lewis acid to be used in the
reaction include boron halides such as boron
trifluoride-methanol and the like, etc.
Examples of the basic solution to be used include aqueous solutions of alkali metal carbonates such as a sodium carbonate aqueous solution, sodium hydrogen carbonate aqueous solution, potassium carbonate aqueous solution, potassium hydrogen carbonate aqueous solution and the like.
The Lewis acid is used usually in a proportion of 1 to 10 mol, and the base in the basic solution is used usually in a proportion of 1 to 20 mol with respect to 1 mol of the compound (12-c) .
The reaction temperature in the process of reacting the compound (12-c) with the Lewis acid is usually in the range of 10 to 100°C, and the reaction time thereof is in the range of 0.5 to 24 hours.
After completion of the reaction of the compound (12-c) with the Lewis acid, the reaction mixture is cooled to room temperature, the solvent is distilled, and the resultant residue can be used as it is in the process of treating with a basic solution.
The treatment temperature in the process of treating with a basic solution is usually in the range of 0 to 25°C, and the treatment time thereof is usually in the range of 0.1 to 2 hours.
After treatment with a basic solution, the compound (19) can be isolated by performing post treatment operations such as, for example, distillation off of the solvent, extraction of the reaction mixture with an organic solvent, drying of the organic layer,
concentration thereof and the like. The isolated compound (19) can also be further purified by
chromatography, re-crystallization and the like. (Production Method 14)
Among inventive compounds, a compound (1-b) in which n represents 1 and Q1 represents an oxygen atom can be produced by reacting a compound (1-a) in the presence of an oxidizer.
Figure imgf000093_0001
[wherein, R1 , R2 , R3 , R , R5 , R6 , R7 and R8 represent the same meaning as described above.]
The reaction is carried out usually in the presence of a solvent.
Examples of the solvent to be used in the reaction include aliphatic halogenated hydrocarbons such as dichloromethane , chloroform and the like, acetic acid, water and mixtures thereof.
Examples of the oxidizer to be used in the reaction include carboxylic acid peroxides such as 3- chloroperbenzoic acid and the like, and hydrogen
peroxide solution, and the like.
The oxidizer is used usually in a proportion of 1 to
3 mol with respect to 1 mol of the compound (1-a) .
The reaction temperature of the reaction is usually in the range of -20 to 100°C, and the reaction time thereof is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (1-b) can be isolated by performing post treatment operations such as extraction of the reaction mixture with an organic solvent, washing of the organic layer with an aqueous solution of a reducing agent (for example, sodium sulfite, sodium thiosulfate) and an aqueous solution of a base (for example, sodium hydrogen
carbonate) if necessary, and drying, concentration thereof and the like. The isolated compound (1-b) can also be further purified by chromatography, re- crystallization and the like.
(Production Method 15)
Among inventive compounds, a compound (4-m) in which n represents 0 and Q1 represents an oxygen atom can be produced by reacting a compound (4-n), an amine compound represented by formula (4-g) (hereinafter, referred to as a compound (4-g)) and a base.
Figure imgf000094_0001
[wherein, R1 , R2 , R3 , R4 , R5 , R6 , R7 , R15 and R16 represent the same meaning as described above, and R ,1J 5 - a represents a phenyl group optionally substituted by at least one member selected from Group X.]
The reaction is carried out usually in the presence of a solvent. Examples of the solvent to be used in the reaction include THF, nitriles such as acetonitrile and the like, acid amides such as DMF, NMP and the like, sulfoxides such as DMSO and the like, ethers such as t-butyl methyl ether, ethylene glycol dimethyl ether, 1,4-dioxane and the like, aromatic hydrocarbons such as toluene, xylene and the like, halogenated hydrocarbons such as
dichloromethane, chloroform, chlorobenzene ,
dichlorobenzene and the like and mixtures thereof.
The amine compound (4-g) is used usually in a proportion of 1 to 10 mol with respect to 1 mol of the compound (4-n) .
When the amine compound (4-g) is in the form of a salt such as a hydrochloride, sulfuric acid salt or the like, a base is used.
Examples of the base to be used include alkali metal carbonates such as sodium carbonate, potassium carbonate and the like, tertiary amines such as triethylamine , diisopropylethylamine and the like, nitrogen-containing aromatic hydrocarbons such as pyridine, 4- dimethylaminopyridine and the like, etc. The base is used usually in a proportion of 1 to 10 mol with respect to 1 mol of the amine compound (4-g) .
The reaction temperature of the reaction is usually in the range of 0 to 100°C, and the reaction time thereof is in the range of 0.5 to 24 hours.
After completion of the reaction, the compound (4-m) can be isolated by performing post treatment operations such as extraction of the reaction mixture with an organic solvent, drying of the organic layer, concentration thereof and the like.
Further, the compound (4-m) can be isolated by performing operations such as addition of water,
filtration of the precipitate, drying thereof and the like, after completion of the reaction, as other post treatment operations. The isolated compound (4-m) can also be further purified by chromatography, re- crystallization and the like.
(Production Method 16)
Among inventive compounds, a compound (4-q) in which n represents 0, Q1 represents an oxygen atom, R7
represents a hydrogen atom and R8 represents -C(=0)R14 can be produced by reacting a compound (12-d) with an amine compound.
Figure imgf000096_0001
[wherein, R1 , R2 , R3 , R4 , R5 and R14 represent the same meaning as described above.]
The is carried out usually using a solvent, however, the reaction may also be carried out in the absence of a solvent .
Examples of the solvent to be used in the reaction include THF, alcohols such as methanol, ethanol and the like, nitriles such as acetonitrile and the like, acid amides such as DMF, N P and the like, ethers such as ethylene glycol dimethyl ether, 1,4-dioxane and the like, aromatic hydrocarbons such as toluene, xylene and the like, halogenated hydrocarbons such as
dichloromethane , chloroform, chlorobenzene ,
dichlorobenzene and the like, esters such as ethyl acetate, butyl acetate and the like and mixtures
thereof .
Examples of the amine compound to be used in the reaction include primary amines such as methylamine, ethylamine and the like, secondary amines such as dimethylamine, diethylamine and the like, etc.
The amine compound is used usually in a proportion of 1 to 10 mol with respect to 1 mol of the compound (12-d) .
The reaction temperature of the reaction is usually in the range of 0 to 100°C, and the reaction time thereof is in the range of 0.1 to 48 hours.
After completion of the reaction, the compound (4-q) can be isolated by performing post treatment operations such as distillation off of the solvent, extraction of the reaction mixture with an organic solvent, drying of the organic layer, concentration thereof and the like. The isolated compound (4-q) can also be further purified by chromatography, re-crystallization and the like.
(Production Method 17)
Among inventive compounds, a compound (12-d) in which n represents 0 and Q represents an oxygen atom can be produced by reacting a compound (12-e) with triphenylphosphine .
Figure imgf000098_0001
(12 - e) (12 - d)
[wherein, R1 , R2 , R3 , R4 , R5 and R14 represent the same meaning as described above.]
The reaction is carried out usually in the presence of a solvent.
Examples of the solvent to be used in the reaction include THF, nitriles such as acetonitrile and the like, acid amides such as D F, NMP and the like, sulfoxides such as DMSO and the like, ethers such as ethylene glycol dimethyl ether, 1,4-dioxane and the like, water and mixtures thereof.
Triphenylphosphine is used usually in a proportion of 1 to 10 mol with respect to 1 mol of the compound (12-e) .
The reaction temperature of the reaction is usually in the range of 0 to 100°C, and the reaction time thereof is in the range of 0.5 to 24 hours.
After completion of the reaction, a compound (12-d) can be isolated by performing post treatment operations such as extraction of the reaction mixture with an organic solvent, drying of the organic layer, concentration thereof and the like.
Further, the compound (12-d) can be isolated by performing operations such as distillation off of the solvent, addition of water, filtration of the
precipitate, drying thereof and the like, after
completion of the reaction, as other post treatment operations. The isolated compound (12-d) can also be further purified by chromatography, re-crystallization and the like.
Some intermediates used in production of the inventive compound are commercially marketed, or can be produced by methods disclosed in known literatures or methods known to those skilled in the art. The
intermediate in the present invention can be produced, for example, by the following method.
(Intermediate Production Method 1)
A compound (2) can be produced by reacting a compound (Ml) with a compound (M2).
Figure imgf000099_0001
[wherein, R1 , R2 , R3 , R4 , R5 and R6 represent the same meaning as described above.]
The reaction is carried out usually in the absence of a solvent, however, the reaction may also be carried out using a solvent.
Examples of the solvent to be used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, 1,4-dioxane and the like, aromatic hydrocarbons such as toluene, xylene and the like and mixtures thereof .
Examples of the compound (M2) to be used in the reaction include N, N-dimethylformamide dimethylacetal, N, N-dimethylacetamide dimethylacetal, N,N- dimethylformamide diethylacetal , N , -dimethylacetamide diethylacetal and the like.
The compound (M2) is used usually in a proportion of 1 to 10 mol with respect to 1 mol of the compound (Ml) .
The reaction temperature of the reaction is usually in the range of 0 to 200°C, and the reaction time thereof is usually in the range of 0.1 to 72 hours.
After completion of the reaction, the compound (2) can be isolated by performing post treatments such as distillation off of the compound (M2) and the solvent, and the like. The isolated compound (2) can also be further purified by chromatography, re-crystallization and the like.
(Intermediate Production Method 2)
A compound (3) can be produced by reacting a
compound (M3) with a compound (16) in the presence of a base.
Figure imgf000100_0001
[wherein, R1 represents the same meaning as described above . ]
The reaction is carried out usually in the presence of a solvent.
Examples of the solvent to be used in the reaction include water, THF, nitriles such as acetonitrile and the like, acid amides such as D F, N P and the like, sulfoxides such as DMSO and the like and mixtures thereof .
Examples of the base to be used in the reaction include alkali metal hydrides such as sodium hydride, potassium hydride and the like, alkali metal carbonates such as sodium carbonate, sodium hydrogen carbonate, potassium carbonate, potassium hydrogen carbonate and the like and mixtures thereof, and the like..
The compound (16) is used usually in a proportion of
1 to 10 mol and the base is used usually in a proportion of 1 to 10 mol with respect to 1 mol of the compound (M3) .
The reaction temperature of the reaction is usually in the range of 0 to 100°C, and the reaction time thereof is in the range of 0.5 to 36 hours.
After completion of the reaction, the compound (3) can be isolated by performing post treatment operations such as distillation off of the solvent, rendering the reaction mixture acidic using hydrochloric acid and the like, then, extraction with an organic solvent, drying of the organic layer, concentration thereof and the like. The isolated compound (3) can also be further purified by re-crystallization and the like. (Intermediate Production Method 3)
A compound (4-c) can be produced by reacting a compound (5) with an acid anhydride represented . by formula (M4) (hereinafter, referred to as a compound (M4) ) .
Figure imgf000102_0001
[wherein, R1 , R2 , R3 , R4 , R5 , R6 , L4 x , A4 and q
represent the same meaning as described above.]
The reaction is carried out usually in the presence of a solvent.
Examples of the solvent to be used in the reaction include aromatic hydrocarbons such as toluene, xylene and the like, halogenated hydrocarbons such as
chlorobenzene , bromobenzene , dichlorobenzene and the like, and mixtures thereof, and the like.
The compound (M4) is used usually in a proportion of 1 to 5 mol with respect to 1 mol of the compound (5) .
The reaction temperature of the reaction is usually in the range of 50 to 200°C, and the reaction time thereof is in the range of 0.5 to 24 hours.
After completion of the reaction, the compound (4-c) can be isolated by performing post treatments such as filtration of the precipitate, drying thereof and the like. The isolated compound (4-c) can also be further purified by chromatography, re-crystallization and the like.
(Intermediate Production Method 4)
A compound (16) can be produced by reacting a compound (M5) with thionyl chloride (hereinafter, referred to as a compound (M6)) or oxalyl chloride
(hereinafter, referred to as a compound (M7)).
CIS(0)CI
(M6)
Figure imgf000103_0001
(M7)
[wherein, R14 represents the same meaning as described above . ]
The reaction is carried out in the presence of a solvent or in the absence of a solvent.
Examples of the solvent to be used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, 1,4-dioxane and the like, aromatic hydrocarbons such as toluene, xylene and the like, halogenated hydrocarbons such as dichloromethane , chloroform, chlorobenzene , dichlorobenzene and the like and mixtures thereof.
The compound (M6) or the compound (M7) is used usually in a proportion of 1 to 20 mol with respect to 1 mol of the compound (M5) .
The reaction temperature of the reaction is usually in the range of 0 to 150°C, and the reaction time thereof is in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (16) can be isolated by performing post treatments such as distillation off of the solvent and the compound (M6) or the compound (M7), and the like. The isolated compound (16) can also be further purified by distillation and the like.
(Intermediate Production Method 5)
A compound (12-e) can be produced by reacting a compound (12-b) with sodium azide.
Figure imgf000104_0001
(12 -b) (12-e)
[wherein, R1 , R2 , R3 , R , R5 , R6 " b and R14 represent the same meaning as described above.]
The reaction is carried out usually in the presence of a solvent.
Examples of the solvent to be used in the reaction include THF, nitriles such as acetonitrile and the like, acid amides such as DMF, NMP and the like, sulfoxides such as DMSO and the like, ethers such as ethylene glycol dimethyl ether, 1,4-dioxane and the like, water and mixtures thereof.
Sodium azide is used usually in a proportion of 1 to 10 mol with respect to 1 mol of the compound (12-b) .
The reaction temperature of the reaction is usually in the range of 0 to 100°C, and the reaction time thereof is in the range of 0.5 to 24 hours.
After completion of the reaction, the compound (12- e) can be isolated by performing post treatment
operations such as extraction of the reaction mixture with an organic solvent, drying of the organic layer, concentration thereof and the like. The isolated compound (12-e) can also be further purified by
chromatography, re-crystallization and the like.
Specific examples of the inventive compound will be shown below.
In the following tables, Ph represents a phenyl group .
Compound represented by formula (1-A)
Figure imgf000105_0001
In the above-described formula (1-A), substituents such as R2 , R6 , R7 , Q1 and n are combined as described in (Table 1) to (Table 4). Table 1
R2 R6 R7 Q1 n
H H H 0 0
F H H 0 0
CI H H 0 0
Br H H 0 0
H CI H 0 0
F CI H 0 0
H Br H 0 0
F Br H 0 0
H H CH3 0 0
H H CH2CH3 0 0
H H CH2CH2CH3 0 0
H H CH(CH3)2 0 0
H H CH2Ph 0 0
H H CH2-cyclopropyl 0 0
H H CH2CF3 0 0
H H H 0 1
F H H 0 1
CI H H 0 1
Br H H 0 1
H CI H 0 1
F CI H 0 1
H Br H 0 1
F Br H 0 1
H H CH3 0 1
Table 2
R2 R6 R7 Q1 n
H H CH2CH3 0 1
H H CH2CH2CH3 0 1
H H CH2Ph 0 1
H H CH2-cyclopropyl 0 1
H H CH2CF3 0 1
F H CH3 0 0
F H CH2CH3 0 0
F H CH2CH2CH3 0 0
F H CH(CH3)2 0 0
F H CH2Ph 0 0
F H CH2-cyclopropyl 0 0
F H CH2CF3 0 0
F H CH3 0 1
F H CH2CH2CH3 0 1
F H CH(CH3)2 0 1
F H CH2Ph 0 1
F H CH2-cyclopropyl 0 1
F H CH2CF3 0 0
H CI CH3 0 0
H CI CH2CH3 0 0
H CI CH2CH2CH3 0 0
H CI CH2Ph 0 0
H CI CH2-cyclopropyl 0 0
H CI CH2CF3 0 0
Table 3
Figure imgf000108_0001
Table 4
R2 R6 R7 Q1 n
H H CH2-cyclopropyl S 0
H H CH2CF3 S 0
H H H s 1
H H CH3 s 1
H H CH2CH3 s 1
H H CH2CH2CH3 s 1
H H CH2Ph s 1
H H CH2-cyclopropyl s 1
H H CH2CF3 s 1 Compound represented by formula (1-B)
Figure imgf000109_0001
In the above-described formula (1-B), substituents such as R1 , R2 , R3 , R4 , R5 , R6 , R14 , Q1 and n are combined as described in (Table 5) to (Table 12).
Table 5
R1 R2 R3 R4 R5 R6 R14
Q1 n
H H H H H H CH3 0 0
H H H H H H CH2CH3 0 0
H H H H H H CH2CH2CH3 0 0
H H H H H H CH(CH3)2 0 0
H H H H H H CH2CH2CH2CH3 0 0
H H H H H H CH(CH3)3 0 0
H H H H H H CH2CH (CH3) 2 0 0
H H H H H H CH (CH3) CH2 (CH3) 0 0
H H H H H H CH (CH3) CH2CH2CH3 0 0
H H H H H H CH2 CH2 C H2 CH2 CH2CH 3 0 0
H H H H H H CH2CH2 C H2 CH(CH3)2 0 0
H H H H H H CH2C1 0 0
H H H H H H CH2CH2CH2C1 0 0
H H H H H H CH2CH2CH2Br 0 0
H H H H H H CH2CH2CH2CH2C1 0 0
H H H H H H CH2 CH2 C H2CH2Br 0 0
H H H H H H CH=CH2 0 0
H H H H H H CH=CHCH3 0 0
H H H H H H cyclopropyl 0 0
H H H H H H 1-methylcyclopropyl 0 0
H H H H H H 2-methylcyclopropyl 0 0
H H H H H H 2, 2-difluoro 0 0 cyclopropyl
H H H H H H 2, 2, 3, 3, -tetrafluoro 0 0 cyclopropyl
H H H H H H 2-cyanocyclopropyl 0 0
H H H H H H 2, 2, 3, 3, -tetrafluoro 0 0 cyclopropyl
H H H H H H 2-cyanocyclopropyl 0 0
H H H H H H cyclobuthyl 0 0
Table 6
R1 R2 R3 R4 R5 R6 R14 Q1 n
H H H H H H cyclobuthyl 0 0
H H H H H H 1-methylcyclobuthyl 0 0
H H H H H H cyclopentyl 0 0
H H H H H H 1-methylcyclopentyl 0 0
H H H H H H cyclohexyl 0 0
H H H H H H 1-methylcyclohexyl 0 0
H H H H H H 2-methylcyclohexyl 0 0
H H H H H H 3-methylcyclohexyl 0 0
H H H H H H 4 -methylcyclohexyl 0 0
H H H H H H CF3 0 0
H H H H H H CH2CF3 0 0
H H H H H H CF2CF3 0 0
H H H H H H CH2Ph 0 0
H H H H H H CH2-cyclopropyl 0 0
H H H H H H CH2OCH3 0 0
H H H H H H CH2OCH2CH3 0 0
H H H H H H CH2CH2OCH3 0 0
H H H H H H CH2CH2CH=CH2 0 0
CI H H H H H CH3 0 0
CI H H H H H CH2CH3 0 0
CI H H H H H cyclopropyl 0 0
CH3 H H H H H CH3 0 0
CH3 H H H H H CH2CH3 0 0
CH3 H H H H H cyclopropyl 0 0
Table 7
R1 R2 R3 R4 R5 R6 R14 Q1 n
H F H H H H CH3 0 0
H F H H H H CH2CH3 0 0
H F H H H H cyclopropyl 0 0
H F H H H H CF3 0 0
H CI H H H H CH3 0 0
H CI H H H H CH2CH3 0 0
H CI H H H H cyclopropyl 0 0
H CI CI H H H CH3 0 0
H Br H H H H CH3 0 0
H Br H H H H CH2CH3 0 0
H Br H H H H cyclopropyl 0 0
H Br H H H H CF3 0 0
H Ph H H H H CH3 0 0
H Ph H H H H CH2CH3 0 0
H Ph H H H H cyclopropyl 0 0
H Ph H H H H CF3 0 0
H CH3 H H H H CH3 0 0
H CH3 H H H H CH2CH3 0 0
H CH3 H H H H cyclopropyl 0 0
H CH3 H H H H CF3 0 0
H CF3 H H H H CH3 0 0
H CF3 H H H H CH2CH3 0 0
H CF3 H H H H cyclopropyl 0 0
H CF3 H H H H CF3 0 0
Table 8
R R R3 R4 R5 R6 R14 Q1 n
1 2
H H CI H H H CH3 0 0
H H CI H H H CH2CH3 0 0
H H CI H H H cyclopropyl 0 0
H H CH3 H H H CH3 0 0
H H CH3 H H H CH2CH3 0 0
H H CH3 H H H cyclopropyl 0 0
H H CF3 H H H CH3 0 0
H H CF3 H H H CH2CH3 0 0
H H CF3 H H H cyclopropyl 0 0
H H H CI H H CH3 0 0
H H H CI H H CH2CH3 0 0
H H H CI H H cyclopropyl 0 0
H H H CH3 H H CH3 0 0
H H H CH3 H H CH2CH3 0 0
H H H CH3 H H cyclopropyl 0 0
H H H H CI H CH3 0 0
H H H H CI H CH2CH3 0 0
H H H H CI H cyclopropyl 0 0
H H H H CH3 H CH3 0 0
H H H H CH3 H CH2CH3 0 0
H H H H CH3 H cyclopropyl 0 0
H H H H -C (=0) OCH3 H CH3 0 0
H H H H -C (=0) OCH3 H CH2CH3 0 0
H H H H -C (=0) OCH3 H cyclopropyl 0 0
Table 9
Figure imgf000114_0001
Table 10
Figure imgf000115_0001
Table 11
R1 R2 R3 R4 R5 R6 R14 Q1 n
H H H H H H 2-methylphenyl 0 0
H H H H H H 3-methylphenyl 0 0
H H H H H H 4 -methylphenyl 0 0
H H H H H H 2-nitrophenyl 0 0
H H H H H H 3-nitrophenyl 0 0
H H H H H H 4-nitrophenyl 0 0
H H H H H H tetrahydrofuran-2 -yl- 0 0
H H H H H H tetrahydrofuran-3-y1- 0 0
H H H H H H furan-2-yl- 0 0
H H H H H H thiophen-2-yl- 0 0
H H H H H H furan-3-yl- 0 0
H H H H H H thiophen-3-yl- 0 0
H H H H H H pyridine-2-yl- 0 0
H H H H H H pyridine-3-yl- 0 0
H H H H H H pyridine-4-yl- 0 0
H H H H H H CH3 0 1
H H H H H H CH2CH3 0 1
H H H H H H CH2CH2CH3 0 1
H H H H H H CH(CH3)2 0 1
H H H H H H CH2 C H2CH2CH3 0 1
H H H H H H CH2CH(CH3) 2 0 1
H H H H H H CH (CH3) CH2 (CH3) 0 1
H H H H H H CH (CH3) CH2C H2 CH3 0 1
H H H H H H CH2C1 0 1
Table 12
Figure imgf000117_0002
Compound represented by formula (1-C)
Figure imgf000117_0001
In the above-described formula (1-C), substituents such as R2 , R6 , R14 and n are combined as described in (Table 13) . Table 13
Figure imgf000118_0002
Compound represented by formula
Figure imgf000118_0001
In the above-described formula (1-D), substituents such as R2 , R6 , R8 , R14 and n are combined as described in (Table 14) to (Table 17).
Table 14
R2 R6 R8 R14 n
H H -C (=0) CH3 CH3 0
H H -C (=0) CH3 CH2CH3 0
H H -C (=0) CH3 CH2CH2CH3 0
H H -C (=0) CH3 CH(CH3)2 0
H H -C (=0) CH3 CH2CH2CH2 CH3 0
H H -C (=0) CH3 CH=CHCH3 0
H- H -C (=0) CH3 C(CH3)3 0
H H -C (=0) CH3 cyclopropyl 0
H H -C (=0) CH3 CF3 0
H H -C (=0) CH2CH3 cyclopropyl 0
H H -C (=0) -cyclopropyl cyclopropyl 0
H H -C (=0) CH2CH3 CH2CH3 0
H H -C (=0) CH3 CH3 1
H H -C (=0) CH3 CH2CH3 1
H H -C (=0) CH3 cyclopropyl 1
H H -C (=0) CH2CH3 cyclopropyl 1
H H -C (=0) -cyclopropyl cyclopropyl 1
H H -C (=0) CH2CH3 CH2CH3 1
F H -C (=0) CH3 CH3 0
F H -C (=0) CH3 CH2CH3 0
F H -C (=0) CH3 cyclopropyl 0
F H -C (=0) CH2CH3 cyclopropyl 0
F H -C (=0) -cyclopropyl cyclopropyl 0
F H -C (=0) CH2CH3 CH2CH3 0
Table 15
R2 R6 R8 R14 n
CI H -C (=0) CH3 CH3 0
CI H -C (=0) CH3 cyclopropyl 0
CI H -C (=0) CH2CH3 cyclopropyl 0
CI H -C (=0) -cyclopropyl cyclopropyl 0
Br H -C (=0) CH3 CH3 0
Br H -C (=0) CH3 cyclopropyl 0
Br H -C (=0) -cyclopropyl cyclopropyl 0
H NH2 -C (=0) -cyclopropyl cyclopropyl 0
F H -C (=0) CH3 cyclopropyl 1
F H -C (=0) -cyclopropyl cyclopropyl 1
CI H -C (=0) CH3 cyclopropyl 1
CI H -C (=0) -cyclopropyl cyclopropyl 1
Br H -C (=0) CH3 cyclopropyl 1
Br H -C (=0) -cyclopropyl cyclopropyl 1
H CI -C (=0) CH3 CH3 0
H CI -C (=0) -cyclopropyl cyclopropyl 0
H Br -C (=0) CH3 CH3 0
H Br -C (=0) CH3 CH2CH3 0
H Br -C (=0) CH3 cyclopropyl 0
H Br -C (=0) CH2CH3 cyclopropyl 0
H Br -C (=0) -cyclopropyl cyclopropyl 0
H Br -C (=0) CH2CH3 CH2CH3 0
H CH3 -C (=0) CH3 CH3 0
H Br -C (=0) cyclopropyl cyclopropyl 1
Table 16
R2 R6 R8 R14 n
H H CH3 CH3 0
H H CH3 CH2CH3 0
H H CH3 CH2CH2CH3 0
H H CH3 CH(CH3)2 0
H H CH3 CH2CH2CH2CH3 0
H H CH3 CH=CHCH3 0
H H CH3 C(CH3)3 0
H H CH3 cyclopropyl 0
H H CH3 CF3 0
H H CH2CH3 CH3 0
H H CH2CH3 CH2CH3 0
H H CH2CH3 cyclopropyl 0
H H CH2OCH3 CH3 0
H H CH2OCH3 CH2CH3 0
H H CH2OCH3 cyclopropyl 0
H H CH2OCH2CH3 CH3 0
H H CH2OCH2CH3 CH2CH3 0
H H CH2OCH2CH3 cyclopropyl 0
H H CH2OCH2Ph CH3 0
H H CH2OCH2Ph CH2CH3 0
H H CH2OCH2Ph cyclopropyl 0
H H CH2Ph CH3 0
H H CH2Ph cyclopropyl 0
H H CH2-cyclopropyl cyclopropyl 0
Table 17
Figure imgf000122_0002
Compound represented by formula (1-E)
Figure imgf000122_0001
In the above-described formula (1-E), substituents such as R2 , R6 , R8 , R14 and n are combined as described in (Table 18), (Table 19).
Table 18
R2 R6 R8 R14 n
H H H CH3 0
H H H CH2CH3 0
H H H CH2CH2CH3 0
H H H cyclopropyl 0
H H H CH2CH2CH2C1 0
H H H Ph 0
H H CH3 CF3 0
H H CH3 CH3 0
H H CH3 CH2CH3 0
H H CH3 cyclopropyl 0
H H -C (=0) CH3 CH3 0
H H -C (=0) CH3 cyclopropyl 0
H H H CH3 1
H H H CH2CH3 1
H H H cyclopropyl 1
H H CH3 CH3 1
H H CH3 CH2CH3 1
H H CH3 cyclopropyl 1
H H -C (=0) CH3 CH3 1
H H -C (=0) CH3 cyclopropyl 1
F H H CH3 0
F H H cyclopropyl 0
F H CH3 CH3 0
F H CH3 cyclopropyl 0
Table 19
Figure imgf000124_0002
Compound represented by formula
Figure imgf000124_0001
In the above-described formula (1-F), substituents such as R2 , R6 , R8 , R15 and n are combined as described in (Table 20), (Table 21) .
Table 20
R2 R6 R8 R15
n
H H H CH3 0
H H H CH2 CH3 0
H H H CH2 CH2CH3 0
H H H CH(CH3) 2 0
H H H CH2CH2CH2 CH3 0
H H H CH2C1 0
H H H CH2CH2C1 0
H H H CH2CH2Br 0
H H H CH2CH2CH2C1 0
H H H CH2CH2CH2Br 0
H H H Ph 0
H H H CH2Ph 0
H H H CH2CH=CH2 0
H H H cyclopropyl 0
H H H CH2-cyclopropyl 0
H H -C (=0) CH3 CH3 0
H H -C (=0) CH3 CH2CH3 0
H H -C (=0) CH3 CH2C1 0
H H -C (=0) CH2CH3 CH2 CH3 0
H H -C (=0) -cyclopropyl CH3 0
H H -C (=0) -cyclopropyl CH2CH3 0
H H CH3 CH3 0
H H CH3 CH2 CH3 0
H H CH2C H3 CH3 0
Table 21
Figure imgf000126_0002
Compound represented by formula
Figure imgf000126_0001
In the above-described formula (1-G) , R represents a
CH3 group, R15 represents a hydrogen atom, substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a CH2CH3 group, R15 represents a hydrogen atom,
substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a CH2 CH2 CH3 group, R15 represents a hydrogen atom, substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents CH(CH3)2 group, R15 represents a hydrogen atom, substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a CH2 CH2 CH2 CH3 group, R15 represents a hydrogen atom, substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a CH2CH(CH3)2 group, R15 represents a hydrogen atom, substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a C(CH3)3 group, R15 represents a hydrogen atom,
substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a CH2 CH2 CH2 CH2 CH3 group, R15 represents a hydrogen atom, substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a cyclopropyl group, R15 represents a hydrogen atom, substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a CH2 -cyclopropyl group, R15 represents a hydrogen atom, substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a CH2OCH3 group, R15 represents a hydrogen atom,
substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a CH2OCH2CH3 group, R15 represents a hydrogen atom, substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a - C(=0)CH3 group, R15 represents a hydrogen atom,
substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a - C(=0)CH2CH3 group, R15 represents a hydrogen atom, substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a - C (=0) CH2 CH2 CH3 group, R15 represents a hydrogen atom, substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23). In the above-described formula (1-G), R represents a C (=0) CH (CH3 ) 2 group, R15 represents a hydrogen atom, substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a C(=0)C(CH3)3 group, R15 represents a hydrogen atom, substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a C (=0) CH2 CH (CH3 ) 2 group, R15 represents a hydrogen atom substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G) , R8 represents a C (=0) CH2 C (CH3 ) 3 group, R15 represents a hydrogen atom, substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a C (=0) C (CH3 ) 2 CH2 CH3 group, R15 represents a hydrogen atom, substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a C ( =0 ) cyclopropyl group, R15 represents a hydrogen atom substituents such as R , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a C (=0) CH2 cyclopropyl group, R15 represents a hydrogen atom, substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a C(=0)OCH3 group, R15 represents a hydrogen atom,
substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a - C(=0)OCH2CH3 group, R15 represents a hydrogen atom, substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a - C(=0)OPh group, R15 represents a hydrogen atom,
substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a CH3 group, R15 represents CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23) .
In the above-described formula (1-G), R8 represents a CH2 CH3 group, R15 represents CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a CH2CH2CH3 group, R15 represents CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a
CH(CH3)2 group, R15 represents CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a CH2 CH2 CH2 CH3 group, R15 represents CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a CH2CH(CH3)2 group, R15 represents CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a C(CH3)3 group, R15 represents CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a CH2 CH2 CH2 CH2 CH3 group, R15 represents CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a cyclopropyl group, R15 represents CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a
CH2 -cyclopropyl group, R15 represents CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a CH2OCH3 group, R15 represents CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a CH2OCH2CH3 group, R15 represents CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a - C(=0)CH3 group, R15 represents CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a - C(=0)CH2CH3 group, R15 represents CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a - C (=0) CH2 CH2 CH3 group, R15 represents CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a - C (=0) CH (CH3 ) 2 group, R15 represents CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a - C(=0)C(CH3)3 group, R15 represents CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a - C (=0) CH2 CH (CH3 ) 2 group, R15 represents CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a - C (=0) CH2 C (CH3 ) 3 group, R15 represents CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G) , R8 represents a - C (=0) C (CH3 ) 2 CH2 CH3 group, R15 represents CH3 ,
substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a - C ( =0 ) cyclopropyl group, R15 represents CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a - C (=0) CH2 cyclopropyl group, R15 represents CH3 ,
substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a - C(=0)0CH3 group, R15 represents CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a - C(=0)OCH2CH3 group, R15 represents CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a - C(=0)0Ph group, R15 represents CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a CH3 group, R15 represents CH2 CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a CH2 CH3 group, R15 represents CH2 CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a CH2 CH2 CH3 group, R15 represents CH2 CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a
CH(CH3)2 group, R15 represents CH2 CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a CH2CH2CH2CH3 group, R15 represents CH2 CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a CH2CH(CH3)2 group, R15 represents CH2 CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a C(CH3)3 group, R15 represents CH2 CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a CH2 CH2 CH2 CH2 CH3 group, R15 represents CH2 CH3 ,
substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23). In the above-described formula (1-G), R8 represents a cyclopropyl group, R15 represents CH2 CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a CH2 -cyclopropyl group, R15 represents CH2 CH3 ,
substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a CH2 OCH3 group, R15 represents CH2 CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a CH2OCH2CH3 group, R15 represents CH2 CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a - C(=0)CH3 group, R15 represents CH2 CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a - C(=0)CH2CH3 group, R15 represents CH2 CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22 ) , (Table 23) .
In the above-described formula (1-G), R8 represents a - C (=0) CH2 CH2 CH3 group, R15 represents CH2 CH3 ,
substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a - C (=0) CH (CH3 ) 2 group, R15 represents CH2 CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a - C(=0)C(CH3)3 group, R15 represents CH2 CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a - C (=0) CH2 CH (CH3 ) 2 group, R15 represents CH2 CH3 ,
substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a - C (=0) CH2 C (CH3 ) 3 group, R15 represents CH2 CH3 ,
substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a - C (=0) C (CH3 ) 2 CH2 CH3 group, R15 represents CH2 CH3 ,
substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a - C (=0) cyclopropyl group, R15 represents CH2 CH3 ,
substituents such as R , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a - C (=0) CH2 cyclopropyl group, R15 represents CH2 CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a - C(=0)0CH3 group, R15 represents CH2 CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a - C(=0)OCH2CH3 group, R15 represents CH2 CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a - C(=0)OPh group, R15 represents CH2 CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a CH3 group, R15 represents CH2 CH2 CH3 , substituents such . as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a CH2 CH3 group, R15 represents CH2 CH2 CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a
CH2 CH2 CH3 group, R15 represents CH2 CH2 CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a CH(CH3)2 group, R15 represents CH2 CH2 CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a CH2CH2CH2CH3 group, R15 represents CH2 CH2 CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a CH2CH(CH3)2 group, R15 represents CH2 CH2 CH3 ,
substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a C(CH3)3 group, R15 represents CH2 CH2 CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a CH2 CH2 CH2 CH2 CH3 group, R15 represents CH2 CH2 CH3 ,
substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a cyclopropyl group, R15 represents CH2 CH2 CH3 ,
substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a CH2 -cyclopropyl group, R15 represents CH2 CH2 CH3 ,
substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a CH2 OCH3 group, Rx 5 represents CH2 CH2 CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a CH2OCH2CH3 group, R15 represents CH2 CH2 CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a - C(=0)CH3 group, R1 represents CH2 CH2 CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a - C(=0)CH2CH3 group, R15 represents CH2 CH2 CH3 ,
substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a - C (=0) CH2 CH2 CH3 group, R15 represents CH2 CH2 CH3 ,
substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a - C (=0) CH (CH3 ) 2 group, R15 represents CH2 CH2 CH3 ,
substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a - C(=0)C(CH3)3 group, R15 represents CH2 CH2 CH3 ,
substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a - C (=0) CH2 CH (CH3 ) 2 group, R15 represents CH2 CH2 CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a - C (=0) CH2 C (CH3 ) 3 group, R15 represents CH2 CH2 CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23). In the above-described formula (1-G), R represents a - C (=0) C (CH3 ) 2 CH2 CH3 group, R15 represents CH2 CH2 CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a - C (=0) cyclopropyl group, R15 represents CH2 CH2 CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a - C (=0) CH2 cyclopropyl group, R15 represents CH2 CH2 CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a - C(=0)OCH3 group, R15 represents CH2 CH2 CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a - C(=0)OCH2CH3 group, R15 represents CH2 CH2 CH3 ,
substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a - C(=0)OPh group, R15 represents CH2 CH2 CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a CH3 group, R15 represents CH(CH3)2, substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) . In the above-described formula (1-G), R represents a CH2 CH3 group, R15 represents CH(CH3)2/ substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a CH2CH2CH3 group, R15 represents CH(CH3)2, substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a CH(CH3)2 group, R15 represents CH(CH3)2, substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a CH2CH2CH2CH3 group, R15 represents CH(CH3)2,
substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a CH2CH(CH3)2 group, R15 represents CH(CH3)2, substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a C(CH3)3 group, R15 represents CH(CH3)2, substituents such as R2 , R6 , R16 and n are combined as described in (Table 22 ) , (Table 23) .
In the above-described formula (1-G), R8 represents a CH2 CH2 CH2 CH2 CH3 group, R15 represents CH(CH3)2,
substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a cyclopropyl group, R15 represents CH(CH3)2, substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
; formula (1-G), R8 represents a CH2 -cyclopropyl group, R15 represents CH(CH3)2, substituents such as R2 , R6 , R16 and n are combined as described in (Table 22),
(Table 23) .
In the above-described formula (1-G), R8 represents a CH2OCH3 group, R15 represents CH(CH3)2, substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a CH2OCH2CH3 group, R15 represents CH(CH3)2, substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a - C(=0)CH3 group, R15 represents CH(CH3)2, substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a - C(=0)CH2CH3 group, R15 represents CH(CH3)2, substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a - C (=0) CH2 CH2 CH3 group, R15 represents CH(CH3)2,
substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a - C (=0) CH (CH3 ) 2 group, R15 represents CH(CH3)2, substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a - C(=0)C(CH3)3 group, R15 represents CH(CH3)2,
substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a - C (=0) CH2 CH (CH3 ) 2 group, R15 represents CH(CH3)2, substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a - C (=0) CH2 C (CH3 ) 3 group, R15 represents CH(CH3)2,
substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a - C (=0) C (CH3 ) 2 CH2 CH3 group, R1 represents CH(CH3)2, substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a - C ( =0 ) cyclopropyl group, R15 represents CH (CH3 ) 2 ,
substituents such as R , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a - C (=0) CH2 cyclopropyl group, R15 represents CH(CH3)2, substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a - C(=0)0CH3 group, R15 represents CH(CH3)2, substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a - C(=0)OCH2CH3 group, R15 represents CH(CH3)2,
substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a - C(=0)OPh group, R15 represents CH(CH3)2, substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a CH3 group, R15 represents CH2 CH2 CH2 CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a
CH2 CH3 group, R15 represents CH2 CH2 CH2 CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G), R8 represents a CH2CH2CH3 group, R15 represents CH2 CH2 CH2 CH3 ,
substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a CH(CH3)2 group, R15 represents CH2 CH2 CH2 CH3 ,
substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a CH2CH2CH2CH3 group, R15 represents CH2 CH2 CH2 CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a CH2CH(CH3)2 group, R15 represents CH2 CH2 CH2 CH3 ,
substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a C(CH3)3 group, R15 represents CH2 CH2 CH2 CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22) , (Table 23) .
In the above-described formula (1-G),, R8 represents a CH2 CH2 CH2 CH2 CH3 group, R15 represents CH2 CH2 CH2 CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a cyclopropyl group, R15 represents CH2 CH2 CH2 CH3 ,
substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a CH2 -cyclopropyl group, R15 represents CH2 CH2 CH2 CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a CH2OCH3 group, R15 represents CH2 CH2 CH2 CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a CH2OCH2CH3 group, R15 represents CH2 CH2 CH2 CH3 ,
substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23). In the above-described formula (1-G), R represents a - C(=0)CH3 group, R15 represents CH2 CH2 CH2 CH3 ,
substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a - C(=0)CH2CH3 group, R15 represents CH2 CH2 CH2 CH3 ,
substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a - C (=0) CH2 CH2 CH3 group, R15 represents CH2 CH2 CH2 CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a - C (=0) CH (CH3 ) 2 group, R15 represents CH2 CH2 CH2 CH3 , substituents such as R , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a - C(=0)C(CH3)3 group, R15 represents CH2 CH2 CH2 CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a - C (=0) CH2 CH (CH3 ) 2 group, R15 represents CH2 CH2 CH2 CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a - C (=0) CH2 C (CH3 ) 3 group, R15 represents CH2 CH2 CH2 CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a - C (=0) C (CH3 ) 2 CH2 CH3 group, R15 represents CH2 CH2 CH2 CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a - C (=0) cyclopropyl group, R15 represents CH2 CH2 CH2 CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a - C (=0) CH2 cyclopropyl group, R15 represents CH2 CH2 CH2 CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a - C(=0)OCH3 group, R15 represents CH2 CH2 CH2 CH3 ,
substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a - C(=0)OCH2CH3 group, R15 represents CH2 CH2 CH2 CH3 , substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23).
In the above-described formula (1-G), R8 represents a - C(=0)0Ph group, R15 represents CH2 CH2 CH2 CH3 ,
substituents such as R2 , R6 , R16 and n are combined as described in (Table 22), (Table 23). Table 22
R2 R6 R16 n
H H CH3 0
H H CH2CH3 0
H H CH2CH2CH3 0
H H CH(CH3)2 0
H H CH2 CH2CH2CH3 0
H H CH2CH(CH3)2 0
H H CH2C (CH3) 3 0
H H C(CH3)3 0
H H CH (CH3) CH2CH3 0
H H CH2CH2 CH2 CH2CH3 0
H H CH (CH3) CH2CH2CH3 0
H H CH2CH2C H2 CH2 CH2 CH3 0
H H cyclopropyl 0
H H cyclobuthyl 0
H H cyclopentyl 0
H H cyclohexyl 0
H H CH2-cyclopropyl 0
H H CH2-cyclobuthyl 0
H H CH2-cyclopentyl 0
H H CH2-cyclohexyl 0
H H CH (CH3) -cyclopropyl 0
H H CH (CH3) -cyclobuthyl 0
H H Ph 0
H H CH2Ph 0
H H CH2- (2-ClPh) 0
H H CH2- (3-ClPh) 0
H H CH2- (4-ClPh) 0
H H CH2- (2-FPh) 0
H H CH2- (3-FPh) 0
H H CH2- (4-FPh) 0
H H CH2- (2-CH3Ph) 0
H H CH2- (3-CH3Ph) 0
H H CH2- (4-CH3Ph) 0
H H CH2- (2-CF3Ph) 0
H H CH2- (3-CF3Ph) 0
H H CH2- (4-CF3Ph) 0
H H CH2- (2-OCH3Ph) 0
H H CH2- (3-OCH3Ph) 0
H H CH2- (4-OCH3Ph) 0
H H CH2CH=CH2 0 Table 22 (cotinued)
R2 R6 R16 n
H H CH (CH3) CH=CH2 0
H H CH (CH3) CH=C (CH3) 2 0
Table 23
R2 R6 R16 n
H H CH2C≡CH 0
H H CH2C≡CCH3 0
H H CH2C≡CCH2CH3 0
H H CH (CH3) C≡CH 0
H H CH (CH3) C≡CCH3 0
H H CH2CF3 0
H H CH2CH2CF3 0
H H CH2CH2C1 0
H H CH2CH2Br 0
H H CH2CH2CH2C1 0
H H CH2CH2CH2Br 0
H H CH3 1
H H CH2CH3 1
H H CH2CH2CH3 1
H H CH(CH3)2 1
H H CH2CH2CH2CH3 1
H H CH2CH(CH3)2 1
H H cyclopropyl 1
H H CH2-cyclopropyl 1
H H CH2Ph 1
H H CH2CH=CH2 1
H H CH2C≡CH 1
F H CH3 0
F H CH2CH3 0
F H CH2CH2CH3 0
F H CH(CH3)2 0
F H CH2CH2CH2CH3 0
F H CH2CH (CH3) 2 0
F H cyclopropyl 0
F H CH2-cyclopropyl 0
F H CH2Ph 0
F H CH2CH=CH2 0
F H CH2C≡CH 0 Table 23 (continued)
Figure imgf000150_0003
Compound represented by formula (1-H)
Figure imgf000150_0001
In the above-described formula (1-H), substituents such as R2 and n are combined as described in (Table 24) .
Com ound represented by formula
Figure imgf000150_0002
In the above-described formula (1-1), substituents such as R2 and n are combined as described in (Table 24) .
Compound represented by formula
Figure imgf000151_0001
In the above-described formula (1-J), substituents such as R2 and n are combined as described in (Table 24) . Compound represented by formula (1-K)
Figure imgf000151_0002
In the above-described formula (1-K), substituents such as R2 and n are combined as described in (Table 24).
Table 24
Figure imgf000151_0003
Compound represented by formula (1-L)
Figure imgf000152_0001
In the above-described formula (1-L), substituents such as R2 , R16 , Q3 , L4 and n are combined as described in (Table 25) .
Compound represented by formula (1-M)
Figure imgf000152_0002
In the above-described formula (1-M), substituents such as R2 , R16 , Q3 , L4 and n are combined as described in (Table 25) .
Table 25
Figure imgf000153_0002
Compound represented by formula (1-N)
Figure imgf000153_0001
In the above-described formula (1-N), substituents such as R2 , R16 , L4 and n are combined as described in (Table 26) . Compound represented by formula (1-0)
Figure imgf000154_0001
In the above-described formula (1-0), substituents such as R2 , R16 , L4 and n are combined as described in (Table 26) .
Table 26
R2 R16 L4 n
H - 0 0
F - O 0
CI - 0 0
Br - 0 0
H - 0 1
F - 0 1
H H N 0
H CH3 N 0
H CH2CH3 N 0
H CH(CH3)2 N 0
H CH2-cyclopropyl N 0
F H N 0
F CH3 N 0
H CH2CH3 N 0
H CH(CH3)2 N 0
H CH2-cyclopropyl N 0
H H N 1
H CH3 N 1
H CH2CH3 N 1
H CH(CH3)2 N 1
H CH2-cyclopropyl N 1 Examples of pests on which the inventive compound exhibits an effect include harmful arthropods such as harmful insects, harmful mites and the like, and
specific examples thereof include the following
organisms .
Hemiptera:
Planthoppers ( Delphacidae ) such as small brown planthopper (Laodelphax striatellus), brown rice
planthopper (Nilaparvata lugens), white-backed rice planthopper (Sogatella furcifera) and the like;
leafhoppers ( Deltocephalidae ) such as green rice
leafhopper (Nephotettix cincticeps), green rice
leafhopper (Nephotettix virescens) , tea green leafhopper (Empoasca onukii) and the like; aphids (Aphididae) such as cotton aphid (Aphis gossypii), green peach aphid (Myzus persicae), cabbage aphid (Brevicoryne brassxcae), piraea aphid (Aphis spiraecola), potato aphid
(Macrosiphum euphorbiae), foxglove aphid (Aulacorthum solani), oat bird-cherry aphid (Rhopalosiphum padi), tropical citrus aphid (Toxoptera citricidus), mealy plum aphid (Hyalopterus pruni) and the like; stink bugs
( Pentatomidae ) such as green stink bug (Nezara
antennata) , bean bug (Riptortus clavetus), rice bug (Leptocorisa chinensis), white spotted spined bug
(Eysarcoris parvus), stink bug (Halyomorpha mista) and the like; whiteflies (Aleyrodidae ) such as greenhouse whitefly (Trialeurodes vaporariorum) , sweetpotato whitefly (Bemisia tabaci) , citrus whitefly (Dialeurodes citri), citrus spiny white fly (Aleurocanthus spiniferus) and the like; scales (Coccidae) such as Calfornia red scale (Aonidiella aurantii), San Jose scale (Comstockaspis perniciosa), citrus north scale (Unaspis citri), red wax scale (Ceroplastes rubens), cottonycushion scale (Icerya purchasi), Japanese
mealybug (Planococcus kraunhiae), Cosmstock mealybug ( Pseudococcus longispinis ) , white peach scale
(Pseudaulacaspis pentagona) and the like; lace bugs (Tingidae); cimices such as Cimex lectularius and the like; psyllids (Psyllidae); etc.
Lepidoptera :
Pyralid moths (Pyralidae) such as rice stem borer (Chilo suppressalis ) , yellow rice borer (Tryporyza incertulas), rice leafroller (Cnaphalocrocis medinalis), cotton leafroller (Notarcha derogata) , Indian meal moth (Plodia interpunctella ) , oriental corn borer (Ostrinia furnacalis), cabbage webworm (Hellula undalis),
bluegrass webworm (Pediasia teterrellus) and the like; owlet moths (Noctuidae) such as common cutworm
(Spodoptera litura) , beet armyworm (Spodoptera exigua) , armyworm (Pseudaletia separata), cabbage armyworm
(Mamestra brassicae), black cutworm (Agrotis ipsilon) , beet semi-looper (Plusia nigrisigna), Thoricoplusia spp., Heliothis spp., Helicoverpa spp. and the like;
white butterflies (Pieridae) such as common white
(Pieris rapae) and the like; tortricid moths
(Tortricidae ) such as Adoxophyes spp., oriental fruit moth (Grapholita molesta), soybean pod borer (Leguminivora glycinivorella), azuki bean podworm
(Matsumuraeses azukivora), summer fruit tortrix
(Adoxophyes orana fasciata) , smaller tea tortrix
(Adoxophyes honmai.), oriental tea tortrix (Homona magnanima) , apple tortrix (Archips fuscocupreanus ) , codling moth (Cydia pomonella) and the like; leafblotch miners (Gracillariidae ) such as tea leafroller
(Caloptilia theivora), apple leafminer ( Phyllonorycter ringoneella) and the like; Carposinidae such as peach fruit moth (Carposina niponensis) and the like;
lyonetiid moths ( Lyonetiidae ) such as Lyonetia spp. and the like; tussock moths ( Lymantriidae ) such as Lymantria spp., Euproctis spp. and the like; yponomeutid moths ( Yponomeutidae ) such as diamondback (Plutella
xylostella) and the like; gelechiid moths (Gelechiidae ) such as pink bollworm ( Pectinophora gossypiella), potato tubeworm (Phthorimaea operculella) and the like; tiger moths and allies (Arctiidae) such as fall webworm
(Hyphantria cunea) and the like; tineid moths (Tineidae) such as casemaking clothes moth (Tinea translucens ) , webbing clothes moth (Tineola bisselliella) and the like; etc. Thysanoptera :
Thrips (Thripidae) such as yellow citrus thrips ( Frankliniella occidentalis ) , melon thrips (Thrips palmi), yellow tea thrips (Scirtothrips dorsalis), onion thrips (Thrips tabaci), flower thrips (Frankliniella intonsa) and the like, etc. Diptera :
Culices such as common mosquito (Culex pipiens pallens), Cluex tritaeniorhynchus , Cluex
quinquefasciatus and the like; Aedes spp. such as yellow fever mosquito (Aedes aegypti), Asian tiger mosquito (Aedes albopictus) and the like; Anopheles spp. such as Anopheles sinensis and the like; chironomids
( Chironomidae ) ; house flies (Muscidae) such as Musca domestica, Muscina stabulans and the like; blow flies (Calliphoridae ) ; flesh flies ( Sarcophagidae ) ; little house flies (Fanniidae); anthomyiid flies (Anthomyiidae ) such as seedcorn fly (Delia platura), onion fly (Delia antiqua) and the like; leafminer flies (Agromyzidae ) such as rice leafminer (Agromyza oryzae), little rice leafminer (Hydrellia griseola), tomato leafminer
(Liriomyza sativae), legume leafminer (Liriomyza
trifolii), garden pea leafminer (Chromatomyxa horticola) and the like; gout flies ( Chloropidae ) such as rice stem maggot (Chlorops oryzae) and the like; fruit flies
(Tephritidae ) such as melon fly (Dacus cucurbitae), Meditteranean fruit fly (Ceratitis capitata) and the like; Drosophilidae ; humpbacked flies (Phoridae) such as Megaselia spiracularis and the like; moth flies
( Psychodidae ) such as Clogmia albipunctata and the like; Simuliidae; Tabanidae such as horsefly (Tabanus
trigonus) and the like; stable flies (Stomoxys
calcitrans), etc. .
158
Coleoptera:
Corn root worms (Diabrotica spp.) such as Western corn root worm (Diabrotica virgifera virgifera),
Sourthern corn root worm (Diabrotica undecimpunctata howardi) and the like; scarabs ( Scarabaeidae ) such as cupreous chafer (Anomala cuprea), soybean beetle
(Anomala rufocuprea) , Japanese beetle (Popillia
japonica) and the like; weevils such as maize weevil (Sitophilus zeamais), rice water weevil (Lissorhoptrus oryzophilus ) , azuki bean weevil (Callosobruchus
chinensis), rice curculio ( Echinocnemus squameus), boll weevil (Anthonomus grandis), hunting billbug
( Sphenophorus venatus) and the like; darkling beetles (Tenebrionidae) such as yellow mealworm (Tenebrio molitor) , red flour beetle (Tribolium castaneum) and the like;
leaf beetles (Chrysomelidae ) such as rice leaf beetle (Oulema oryzae), cucurbit leaf beetle (Aulacophora femoralis), striped flea beetle (Phyllotreta striolata), Colorado potato beetle (Leptinotarsa decemlineata) and the like; dermestid beetles ( Dermestidae ) such as varied carper beetle (Anthrenus verbasci), hide beetle
(Dermestes maculates) and the like; deathwatch beetles (Anobiidae) such as cigarette beetle (Lasioderma
serricorne) and the like; Epilachna such as Twenty- eight-spotted ladybird (Epilachna vigintioctopunctata ) and the like; bark beetles (Scolytidae) such as powder- post beetle (Lyctus brunneus), pine shoot beetle (Tomicus piniperda) and the like; false powder-post beetles (Bostrychidae) ; spider beetles (Ptinidae);
longhorn beetles ( Cerambycidae ) such as white-spotted longicorn beetle (Anoplophora malasiaca) and the like; click beetles (Agriotes spp . ) ; Paederus fuscipens, etc.
Orthoptera :
Asiatic locust (Locusta migratoria), African mole cricket (Gryllotalpa africana), rice grasshopper (Oxya yezoensis), rice grasshopper (Oxya japonica), Gryllidae, etc .
Hymenoptera :
Ants (Formicidae) such as pharaoh ant (Monomorium pharaosis), negro ant (Formica fusca japonica), black house ant (Ochetellus glaber) , Pristomyrmex pungens, Pheidole noda, leaf-cutting ant (Acromyrmex spp.), fire ant (Solenopsis spp.) and the like; hornets (Vespidae); bethylid wasps (Betylidae); sawflies ( enthredinidae ) ' such as cabbage sawfly (Athalia rosae), Athalia japonica and the like, etc.
Nematodes
white-tip nematode (Aphelenchoides besseyi),
strawberry bud nematode (Nothotylenchus acris), southern root-knot nematode (Meloidogyne incognita), northern root-knot nematode (Meloidogyne hapla) , javanese root- knot nematode (Meloidogyne javanica), soybean cyst nematode (Heterodera glycines), potato cyst nematode (Globodera rostochiensis ) , coffee root-lesion nematode ( Pratylenchus coffeae), California root-lesion nematode ( Pratylenchus neglectus) and the like .
Blattodea:
German cockroach (Blattella germanica), smokybrown cockroach (Periplaneta fuliginosa) , American cockroach (Periplaneta americana), Periplaneta brunnea, oriental cockroach (Blatta orientalis) and the like;
Acarina :
Spider mites ( Tetranychidae ) such as two-spotted spider mite (Tetranychus urticae) , Kanzawa spider mite (Tetranychus kanzawai), citrus red mite (Panonychus citri), European red mite (Panonychus ulmi), Oligonychus spp. and the like; eriophyid mites ( Eriophyidae ) such as pink citrus rust mite (Aculops pelekassi),
Phyllocoptruta citri, tomato rust mite (Aculops
lycopersici ) , purple tea mite (Calacarus carinatus), pink tea rust mite (Acaphylla theavagran) , Eriophyes chibaensis, apple rust mite (Aculus schlechtendali ) and the like; tarosonemid mites ( Tarsonemidae ) such as broad mite (Polyphagotarsonemus latus) and the like; false spider mites ( Tenuipalpidae ) such as Brevipalpus
phoenicis and the like; Tuckerellidae ; ticks (Ixodidae) such as Haemaphysalis longicornis, Haemaphysalis flava, Dermacentor taiwanicus, Ixodes ovatus, Ixodes
persulcatus, black legged tick (Ixodes scapularis), Boophilus microplus, Rhipicephalus sanguineus and the like; acarid mites (Acaridae) such as mold mite
(Tyrophagus putrescentiae ) , Tyrophagus similis and the like; house dust mites ( Pyroglyphidae ) such as
Dermatophagoides farinae, Dermatophagoides ptrenyssnus and the like; cheyletide mites (Cheyletidae) such as Cheyletus eruditus, Cheyletus malaccensis, Cheyletus moorei and the like; parasitoid mites ( Dermanyssidae ) such as tropical rat mite (Ornithonyssus bacoti), northern fowl mite (Ornithonyssus sylviarum) , poultry red mite (Dermanyssus gallinae) and the like; chiggers
( Trombiculidae ) such as Leptotrombidium akamushi and the like; spiders (Araneae) such as Japanese foliage spider (Chiracanthium japonicum), redback spider (Latrodectus hasseltii) and the like, etc.
The pest control agent according to the present invention contains the inventive compound and an inert carrier such as a solid carrier, liquid carrier, gaseous carrier. The pest control agent according to the present invention may conatins, if necessary, a
surfactant and other formulation auxiliaries, and formulated into an emulsifiable concentrate, oil
solution, dust, granule, wettable powder, flowable formulation, microcapsule, aerosol, smoking agent, poison bait, resin formulation and the like.
These formulations contain the inventive compound usually in an amount of 0.01 to 95 wt%.
Examples of the solid carrier used in making a formulation include fine powders and granular materials made of clays (kaolin clay, diatomaceous earth,
bentonite, Fubasami clay, acid clay and the like) , synthetic hydrous silicon oxide, talc, ceramic, other inorganic minerals (sericite, quartz, sulfur, activated carbon, calcium carbonate, hydrated silica and the like), chemical fertilizers (ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammonium chloride, and the like), and the like.
Examples of the liquid carrier include water, alcohols (methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol, phenoxyethanol and the like), ketones (acetone, methyl ethyl ketone, cyclohexanone and the like) , aromatic hydrocarbons (toluene, xylene, ethylbenzene , dodecylbenzene , phenylxylylethane , methylnaphthalene and the like) , aliphatic hydrocarbons (hexane, cyclohexane, kerosene, light oil and the like ) , esters (ethyl acetate, butyl acetate, isopropyl myristate, ethyl oleate, diisopropyl adipate, diisobutyl adipate,
propylene glycol monomethyl ether acetate and the like), nitriles ( acetonitrile , isobutyronitrile and the like) , ethers (diisopropyl ether, 1,4-dioxane, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, 3-methoxy-3-methyl-l-butanol and the like ) , acid amides (N, N-dimethylformamide, , N-dimethylacetamide and the like), halogenated hydrocarbons ( dichloromethane , trichloroethane , carbon tetrachloride and the like) , sulfoxides (dimethyl sulfoxide and the like) , propylene carbonate and vegetable oils (soybean oil, cotton seed oil and the like) .
Examples of the gaseous carrier include
fluorocarbons , butane gase, LPG (liquefied petroleum gas), dimethyl ether and carbon dioxide gas.
Examples of the surfactant include nonionic
surfactants usch as polyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, polyethylene glycol fatty acid esters and the like, and anionic surfactants such as alkylsulfonic acid salts, alkylbenzenesulfonic acid salts, alkylsulfuric acid salts and the like.
The other formulation auxiliaries include fixing agents, dispersing agents, coloring agents, stabilizers and the like, and specific examples thereof include casein, gelatin, saccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, synthetic water-soluble polymers (polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acids, etc.), PAP (acid isopropyl phosphate), BHT (2,6- di-tert-butyl-4 -methylphenol ) , BHA (a mixture of 2-tert- butyl-4 -methoxyphenol and 3-tert-butyl-4-methoxyphenol ) .
In the pest control method according to the present invention, the inventive compound can be used as it is without addition of any other components, and usually, the inventive compound is formulated into the form of the pest control agent according to the present
invention describe dabove, and for example, the
formulation is applied to pests or areas where pests live by the same method as for conventional pest control agents, and the emergent pests described above are allowed to contact with or ingest the formulation.
The place where pests inhabit according to the present invention include a paddy field, a dry field, a cultivated field, a tea field, a fruit orchard, a non- cultivated field, a house, a raising seedling tray, a nursery box, nursery soil, a nursery mat, a water cluture medium in a hydroponic farm, and the like.
Examples of such an application method include spray treatment, soil treatment, seed treatment and water cluture medium treatment. The application amount of the pet controlling agent of the present invention can be widely changed depending on an application timing, application place, application method and the like, in the case of use for pest control in the agricultural field, and generally, the amount of the inventive compound is 1 to 10000 g per 10000 m2.
When the pet controlling agent of the present invention is formulated into an emulsifiable concentrate, wettable powder, flowable formulation or the like, the agent is usually diluted with water so that the active ingredient concentration is 0.01 to 10000 ppm before application, and in the case of a granule, dust or the like, it is usually applied as it is. These formulations or water-diluted solutions thereof may be sprayed directly to pests or a plant such as a crop to be protected from pests, and for
controlling pests living in a soil of in a cultivated land, the soil may be treated with these formulations or solutions.
It is also possible that a resin formulation is processed into the form of a sheet or a string, and then used for treatment by winding it around a crop,
disposing it in the vicinity of a crop, laying it on the soil surface at the plant foot, or the like.
When the pest control agent according to the present invention is used for control of pests (for example, fly, mosquito, cockroach) living in a house, the
application amount thereof is usually 0.01 to 1000 mg in terms of the amount of the inventive compound per 1 m2 of treatment area in the case of treatment on a surface, and usually 0.01 to 500 mg in terms of the amount of the inventive compound per 1 m3 of treatment space in the case of treatment in a space. When the pest control agent according to the present invention is formulated into an emulsifiable concentrate, wettable powder, flowable formulation or the like, it is usually diluted with water so that the active ingredient concentration is 0.1 to 1000 ppm before application, while an oil solution, aerosol, smoking agent, poison bait or the like is used as it is.
The compound of the present invention can be used as a pest control agent for cultivated lands such as a dry field, paddy field, lawn, fruit orchard and the like or non-cultivated lands. The compound of the present invention can be used in a cultivated land for growing
"crops" listed below, to control pests in the cultivated land without imparting a chemical injury on the crop, in some cases.
Agricultural crops: corn, rice, wheat, barley, rye, oat,' sorghum, cotton, soybean, peanut, sarrazin, sugar beet, rapeseed, sunflower, sugar cane, tobacco, etc. ;
Vegetables: Solanaceae vegetables (eggplant, tomato, green pepper, hot pepper, potato etc.), Cucurbitaceae vegetables (cucumber, pumpkin, zucchini, watermelon, melon etc.), Cruciferae vegetables (Japanese radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, brown mustard, broccoli, cauliflower etc.), Compositae vegetables (burdock, garland chrysanthemum, artichoke, lettuce etc.), Liliaceae vegetables (Welsh onion, onion, garlic, asparagus etc.), Umbelliferae vegetables
(carrot, parsley, celery, parsnip etc.), Chenopodiaceae vegetables (spinach, Swiss chard etc.), Labiatae
vegetables (Japanese basil, mint, basil etc.),
strawberry, sweat potato, yam, aroid, etc.; Fruit trees: pomaceous fruits (apple, common pear, Japanese pear, Chinese quince, quince etc.), stone fleshy fruits (peach, plum, nectarine, Japanese plum, cherry, apricot, prune etc. ) , citrus plants (Satsuma mandarin, orange, lemon, lime, grapefruit etc.), nuts
(chestnut, walnut, hazel nut, almond, pistachio, cashew nut, macadamia nut etc.), berry fruits (blueberry, cranberry, blackberry, raspberry etc.), grape,
persimmon, olive, loquat, banana, coffee, date, coconut palm, oil palm, etc.;
Trees other than fruit trees: tea, mulberry,
flowering trees (rhododendron, camellia, hydrangea, sasanqua, Japanese star anise, Japanese Cherry, tulip tree, Crape myrtle, fragrant orange-colored olive, etc.), street trees (ash tree, birch, dogwood,
eucalyptus, ginkgo, lilac, maple tree, oak, poplar, cercis, Chinese sweet gum, plane tree, zelkova, Japanese arborvitae, fir tree, Japanese hemlock, needle juniper, pine, spruce, yew, elm, Japanese horse-chestnut, etc.), Sweet viburnum, Largeleaf podocarp, Japanese cedar, Hinoki cypress, croton, Japanese Spindle, Chinese hawthorn, etc.
Lawn: zoysia (Japanese lawn grass, mascarene grass, etc.), Bermuda grass (Cynodon dactylon, etc.), bent grass (creeping bent grass, Agrostis stolonifera,
Agrostis tenuis, etc.), bluegrass (Kentucky bluegrass, rough bluegrass, etc.), fescue (tall fescue, chewing fescue, creeping fescue, etc.), ryegrass (darnel, perennial ryegrass, etc.), cocksfoot, timothy grass, etc . ;
Others: flowering herbs (rose, carnation,
chrysanthemum, Eustoma grandiflorum Shinners (prairie gentian) , gypsophila, gerbera, pot marigold, salvia, petunia, verbena, tulip, aster, gentian, lily, pansy, cyclamen, orchid, lily of the valley, lavender, stock, ornamental kale, primula, poinsttia, gladiolus,
cattleya, daisy, cymbidium, begonia, etc.), biofuel plants (jatropha, curcas, safflower, Camelina alyssum, switch grass, Miscanthus, reed Canary grass, Great reed, kenaf, cassava, willow, algae, etc.), ornamental foliage plants, etc.
The above described "crops" include genetically moedified crops.
Typical examples of pest control agents (including isomers and salts thereof) such as insecticides,
acaricides, nematocides, fungicides, phytohormone agents, plant growth regulators, herbicides and the like, and synergists or crop injury-reducing agents, which can be mixed with the inventive compound, include the following compounds. Examples of the active ingredient of insecticides include:
(1) Organic phosphorus compounds:
Acephate, aluminium phosphide, butathiofos,
cadusafos, chlorethoxyfos , chlorfenvinphos , chlorpyrifos , chlorpyrifos-methyl , cyanophos (CYAP) , diazinon, DCIP (dichlorodixsopropyl ether) ,
dichlofenthion (ECP) , dichlorvos (DDVP), dimethoate, dimethylvinphos , disulfoton, EPN, ethion, ethoprophos, etrimfos, fenthion (MPP) , fenitrothion (MEP) ,
fosthiazate, formothion, hydrogen phosphide, isofenphos, isoxathion, malathion, mesul fenfos , methidathion ( DMTP ) , monocrotophos , naled (BRP) , oxydeprofos (ESP) ,
parathion, phosalone, phosmet (PMP), pirimiphos-methyl , pyridafenthion, quinalphos, phenthoate (PAP),
profenofos, propaphos, prothiofos, pyraclorfos,
salithion, sulprofos, tebupirimfos , temephos,
tetrachlorvinphos , terbufos, thiometon, trichlorphon (DEP), vamidothion, phorate, cadusafos, and the like; (2) Carbamate compounds:
Alanycarb, bendiocarb, benfuracarb, BPMC, carbaryl, carbofuran, carbosulfan, cloethocarb, ethiofencarb, fenobucarb, fenothiocarb, fenoxycarb, furathiocarb , isoprocarb (MIPC) , metolcarb, methomyl, methiocarb, NAC, oxamyl, pirimicarb, propoxur (PHC), X C, thiodicarb, xylylcarb, aldicarb, and the like;
(3) Synthetic pyrethroid compounds:
Acrinathrin, allethrin, benfluthrin, beta- cyfluthrin, bifenthrin, cycloprothrin , cyfluthrin, cyhalothrin, cypermethrin, deltamethrin , esfenvalerate , ethofenprox, fenpropathrin, fenvalerate, flucythrinate , flufenoprox, flumethrin, fluvalinate, halfenprox, imiprothrin, permethrin, prallethrin, pyrethrins, resmethrin, sigma-cypermethrin , silafluofen, tefluthrin, tralomethrin, transfluthrin, tetramethrin, phenothrin, cyphenothrin, alpha-cypermethrin, zeta-cypermethrin, lambda-cyhalothrin, gamma-cyhalothrin , furamethrin, tau- fluvalinate, metofluthrin, profluthrin, dimefluthrin , 2, 3, 5, 6-tetrafluoro-4- (methoxymethyl ) benzyl (EZ)-(IRS, 3RS; IRS, 3SR) -2 , 2-dimethyl-3-prop-l- enycyclopropanecarboxylate , 2,3,5, 6-tetrafluoro-4- methylbenzyl (EZ)-(IRS, 3RS;1RS, 3SR) -2 , 2 -dimethyl-3 - prop-l-enycyclopropanecarboxylate, 2,3,5, 6-tetrafluoro- 4- (methoxymethyl) benzyl (IRS, 3RS;1RS, 3SR)-2,2- dimethyl-3- ( 2-methyl- 1 -propenyl ) cyclopropanecarboxylate, and the like;
(4) Nereistoxin compounds:
Cartap, bensultap, thiocyclam, monosultap, bisultap, and the like;
(5) Neonicotinoid compounds:
Imidacloprid, nitenpyram, acetamiprid, thiamethoxam, thiacloprid, dinotefuran, clothianidin , and the like;
(6) Benzoylurea compounds:
Chlorfluazuron, bistrifluron, diafenthiuron,
diflubenzuron, fluazuron, flucycloxuron, flufenoxuron , hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron, triazuron, and the like;
(7) Phenylpyrazole compounds:
Acetoprole, ethiprole, fipronil, vaniliprole, pyriprole, pyrafluprole, and the like;
(8) Bt toxin insecticides:
Live spores derived from and crystal toxins produced from Bacillus thuringiesis and a mixture thereof; (9) Hydrazine compounds:
Chromafenozide , halofenozide, methoxyfenozide , tebufenozide , and the like;
(10) Organic chlorine compounds:
Aldrin, dieldrin, dienochlor, endosulfan,
methoxychlor , and the like;
(11) Natural insecticides:
Machine oil, nicotine-sulfate ;
(12) Other insecticides:
Avermectin-B , bromopropylate , buprofezin,
chlorphenapyr , cyromazine, D-D ( 1 , 3-Dichloropropene , emamectin-benzoate, fenazaquin, flupyrazofos ,
hydroprene, methoprene, indoxacarb, metoxadiazone , milbemycin-A, pymetrozine, pyridalyl, pyriproxyfen, spinosad, sulfluramid, tolfenpyrad, triazamate,
flubendiamide , lepimectin, arsenic acid, benclothiaz, calcium cyanamide, calcium polysulfide, chlordane, DDT, DSP, flufenerim, flonicamid, flurimfen, formetanate, metarn-ammonium, metam-sodium, methyl bromide, potassium oleate, protrifenbute, spiromesifen, sulfoxaflor, sulfur, metaflumizone, spirotetramat , pyri fluquinazone , spinetoram, chlorantraniliprole, tralopyril,
cyantraniliprole , compounds represented by following formula (A) :
Figure imgf000173_0001
[wherein,
Ra represents a chlorine atom, bromine atom or trifluoromethyl group,
Rb represents a chlorine atom, bromine atom or methyl group,
Rc represents a chlorine atom, bromine atom or cyano group . ]
com ounds represented by following formula (B)
Figure imgf000173_0002
[wherein, Rd represents a chlorine atom, bromine atom or iodine atom. ]
Examples of the active ingredient of acaricides include acequinocyl, amitraz, benzoximate, bifenaate, bromopropylate , chinomethionat , chlorobenzilate, CPCBS ( chlorfenson ) , clofentezine , cyflumetofen, kelthane (dicofol), etoxazole, fenbutatin oxide, fenothiocarb , fenpyroximate , fluacrypyrim, fluproxyfen, hexythiazox, propargite (BPPS) , polynactins, pyridaben, pyrimidifen, tebufenpyrad, tetradifon, spirodiclofen, spiromesifen, spirotetramat , amidoflumet , cyenopyrafen , and the like.
Examples of the active ingredient of nematicides include DCIP, fosthiazate, levamisol,
methyisothiocyanate, morantel tartarate, imicyafos, and the like.
Examples of the active ingredient of fungicides include azole fungicidal compounds such as
propiconazole, prothioconazole , triadimenol, prochloraz, penconazole, tebuconazole, flusilazole, diniconazole , bromuconazole , epoxiconazole, difenoconazole,
cyproconazole, metconazole, tri flumi zole , tetraconazole, myclobutanil , fenbuconazole, hexaconazole,
fluquinconazole , triticonazole , bitertanol, imazalil, flutriafol and the like;
cyclic amine fungicidal compouds such as
fenpropimorph, tridemorph, fenpropidin and the like;
benzimidazole fungicidal compounds such as
carbendezim, benomyl, thiabendazole, thiophanate-methyl and the like;
procymidone, cyprodinil, pyrimethanil ,
diethofencarb, thiuram, fluazinam, mancozeb, iprodione, vinclozolin, chlorothalonil , captan, mepanipyrim, fenpiclonil, fludioxonil, dichlofluanid, folpet,
kresoxim-methyl , azoxystrobin, trifloxystrobin,
fluoxastrobin, picoxystrobin, pyraclostrobin,
dimoxystrobin, pyribencarb, spiroxamine, quinoxyfen, fenhexamid, famoxadone, fenamidone, zoxamide, ethaboxam, amisulbrom, iprovalicarb, benthiavalicarb, cyazofamid, mandipropamid, boscalid, penthiopyrad, metrafenone, fluopiran, bixafen, cyflufenamid, proquinazid,
isotianil, tiadinil and the like.
Examples of the active ingredient of herbicides include :
(1) Phenoxyfatty acid herbicidal compounds
2,4-PA, CP, MCPB, phenothiol, mecoprop, fluroxypyr, triclopyr, clomeprop, riaproanilide and the like;
(2) Benzoic acid herbicidal compounds
2,3,6-TBA, dicamba, clopyralid, picloram,
aminopyralid, quinclorac, quinmerac and the like;
(3) Urea herbicidal compounds
diuron, linuron, chlortoluron , isoproturon,
fluometuron, isouron, tebuthiuron, methabenzthiazuron, cumyluron, daimuron, methyl-daimuron and the like;
(4) Triazine herbicidal compounds
atrazine, ametoryn, cyanazine, simazine, propazine, simetryn, dimethametryn, prometryn, metribuzin,
triaziflam, indaziflam and the like;
(5) Bipyridinium herbicidal compounds
paraquat, diquat and the like;
(6) Hydroxybenzonitrile herbicidal compounds
Bromoxynil, ioxynil and the like;
(7) Dinitroaniline herbicidal compounds
pendimethalin, prodiamine, trifluralin and the like;
(8) Organic phosphorus herbicidal compounds
amiprofos-methyl , butamifos, bensulide, piperophos, anilofos, glyphosate, glufosinate, glufosinate-P , bialaphos and the like;
(9) Carbamate herbicidal compounds
di-allate, tri-allate, EPTC, butylate, benthiocarb, esprocarb, molinate, dimepiperate , swep, chlorpropham, phenmedipham, phenisopham, pyributicarb, asulam and the like;
(10) Acid amide herbicidal compounds
propanil, propyzamide, bromobutide, etobenzanid and the like;
(11) Chloroacetanilide herbicidal compounds
acetochlor, alachlor, butachlor, dimethenamid, propachlor, metazachlor, metolachlor, pretilachlor , thenylchlor, pethoxamid and the like;
(12) Diphenylether herbicidal compounds
acifluorfen-sodium, bifenox, oxyfluorfen, lactofen, fomesafen, chlomethoxynil , aclonifen and the like;
(13) Cyclic imide herbicidal compounds
oxadiazon, cinidon-ethyl , carfentrazone-ethyl , surfentrazone, flumiclorac-pentyl , flumioxazin,
pyraflufen-ethyl , oxadiargyl, pentoxazone, fluthiacet- methyl, butafenacil, benzfendizone, bencarbazone, saflufenacil and the like;
(14) Pyrazole herbicidal compounds
benzofenap, pyrazolate, pyrazoxyfen, topramezone, pyrasulfotole and the like;
(15) Triketone herbicidal compounds
isoxaflutole , benzobicyclon, sulcotrione,
mesotrione, tembotrione, te furyltrione and the like; (16) Aryloxyphenoxypropionic acid herbicidal compounds clodinafop-propargyl , cyhalofop-butyl , diclofop- methyl, fenoxaprop-ethyl , fluazifop-butyl , haloxyfop- methyl, qui zalofop-ethyl , metamifop and the like;
(17) Trioneoxime herbicidal compounds
alloxydim-sodium, sethoxydim, butroxydim, clethodim, cloproxydim, cycloxydim, tepraloxydim, tral koxydim, profoxydim and the like;
(18) Sulfonylurea herbicidal compounds
chlorsulfuron, sulfometuron-methyl , metsulfuron- methyl, chlorimuron-ethyl , tribenuron-methyl ,
triasulfuron, bensulf ron-methyl , thifensulfuron-methyl , pyrazosulfuron-ethyl, primisulfuron-methyl ,
nicosul furon , amidosul furon , cinosulfuron,
imazosulfuron, rimsulfuron, halosulfuron-methyl ,
prosulfuron, ethametsulfuron-methyl , triflusulfuron- methyl, flazasulfuron, cyclosulfamuron, flupyrsulfuron, sulfosulfuron, azimsulfuron, ethoxysulfuron,
oxasulfuron, iodosulfuron-methyl-sodium, foramsulfuron, mesosulfuron-methyl , trifloxysulfuron, tritosulfuron, orthosulfamuron, flucetosulfuron, propyrisulfuron and the like;
(19) Imidazolinone herbicidal compounds
imazamethabenz-methyl , imazamethapyr, imazamox, imazapyr, imazaquin, imazethapyr and the like;
(20) Sulfonamide herbicidal compounds
flumetsulam, metosulam, diclosulam, florasulam, cloransulam-methyl , penoxsulam, pyroxsulam and the like;
(21) Pyrimidinyloxybenzoic acid herbicidal compounds pyrithiobac-sodium, bispyribac-sodium, pyriminobac- methyl, pyribenzoxim, pyriftalid, pyrimisulfan and the like; and
(22) Other herbicidal compounds
bentazon, bromacil, terbacil, chlorthiamid,
isoxaben, dinoseb, amitrole, cinmethylin, tridiphane, dalapon, diflufenzopyr-sodium, dithiopyr, thiazopyr, flucarbazone-sodium, propoxycarbazone-sodium, mefenacet, flufenacet, fentrazamide, cafenstrole, indanofan, oxaziclomefone, benfuresate, ACN, pyridate, chloridazon, norflurazon, flurtamone, diflufenican, picolinafen, beflubutamid, clomazone, amicarbazone , pinoxaden, pyraclonil, pyroxasulfone, thiencarbazone-methyl , aminocyclopyrachlor , ipfencarbazone, methiozolin and the like.
Examples of the active ingredient of synergists include piperonyl butoxide, sesamex, sulfoxide, N-(2- ethylhexyl) -8, 9, 10-trinorborn-5-ene-2 , 3-dicarboxyimide (MGK 264), N-declyimidazole , WARF-antiresistant , TBPT, TPP, IBP, PSCP, methyl iodide (CH3I), t-phenylbutenone , diethylmaleate, D C, FDMC , ETP, and ETN .
EXAMPLES
The present invention will be explained further in detail below by production examples of inventive
compounds and production intermediates of inventive compounds, formulation examples of inventive compounds, test examples and the like, but the present invention is not limited only to these examples.
First, production examples of inventive compounds are shown below. In the production examples, CDC13 represents deuterated chloroform, and DMS0-D6 represents deuterated dimethyl sulfoxide.
Production Example 1
A mixture of 43.6 g of 3-dimethylamino-l- (pyridin-3- yl ) -propenone, 28.9 g of N-acetylglycine and 300 ml of acetic anhydride was stirred with heating at 90°C for 9 hours. After cooling down to room temperature, 200 ml of ethanol was added, and the deposited precipitate was filtrated. The filtrated product was washed with 100 ml of ethanol, and dried under reduced pressure to obtain 25.0 g of N- [2-OXO-6- (pyridin-3-yl) -2H-pyran-3-yl] - acetamide (hereinafter, referred to as the inventive com ound 1 ) .
Figure imgf000179_0001
Inventive compound 1
1 H-NMR (DMSO-D6) δ: 9.80 (1H, s), 9.03-9.00 (1H, m) ,
8.64-8.61 (1H, m) , 8.26 (1H, d) , 8.18-8.15 (1H, m) ,
7.55-7.51 (1H, m) , 7.24 (1H, d) , 2.15 (3H, s).
1 H-NMR (CDCI3) δ: 9.02-9.00 (1H, m) , 8.66-8.63 (1H, m) , 8.39 (1H, d) , 8.08-8.04 (1H, m) , 8.04 (1H, s), 7.39 (1H, dd) , 6.80 (1H, d) , 2.25 (3H, s). Production Example 2
N- [2-OXO-6- (pyridin-3-yl ) -2H-pyran-3-yl ] - propionamide (hereinafter, referred to as the inventive compound 2) was obtained according to the method described in Production Example 1 using propionylamino- acetic acid instead of N-acetylglycine .
Figure imgf000180_0001
Inventive compound 2
1 H-NMR (CDC13) δ: 9.01-9.00 (1H, m) , 8.65-8.63 (1H,
8.40 (1H, d) , 8.07-8.04 (1H, m) , 8.00 (1H, s), 7.40
(1H, m) , 6.80 (1H, d) , 2.45 (2H, q) , 1.26 (3H, t).
Production Example 3
N- [2-ΟΧΟ-6- (pyridin-3-yl ) -2H-pyran-3-yl ] -butylamide (hereinafter, referred to as the inventive compound 3) was obtained according to the method described in
Production Example 1 using butyrylamino-acetic acid instead of N-acet lglycine.
Figure imgf000180_0002
Inventive compound 3
1 H-NMR (CDCI3) δ: 9.01-9.00 (1H, m) , 8.65-8.64 (1H,
8.40 (1H, d) , 8.07-8.06 (1H, m) , 8.05 (1H, s), 7.40 (1H, m) , 6.80 (1H, d) , 2.43-2.39 (2H, q) , 1.79-1.72 (2H, m) , 1.01 (3H, t) .
Production Example 4
N- [2-OXO-6- (pyridin-3-yl ) -2H-pyran-3-yl ] - isobutylamide (hereinafter, referred to as the inventive compound 4) was obtained according to the method
described in Production Example 1 using isobutyrylamino- acetic acid instead of N-acetylglycine .
Figure imgf000181_0001
Inventive compound 4
1 H-NMR (CDC13) δ : 9.02-9.00 (1H, m) , 8.66-8.63 (1H, m) , 8.40 (1H, d) , 8.09-8.05 (1H, m) , 8.03 (1H, s), 7.42-7.38 (1H, m) , 6.81 (1H, t), 2.66-2.57 (1H, m) , 1.27 (6H, d) .
Production Example 5
N- [2-OXO-6- (pyridin-3-yl ) -2H-pyran-3-yl ] -pivaloamide (hereinafter, referred to as the inventive compound 5) was obtained according to the method described in
Production Example 1 using pivaloylamino-acetic acid instead of N-acetylglycine.
Figure imgf000182_0001
Inventive compound 5
1 H-NMR (CDC13) δ: 9.03-9.01 (1H, m) , 8.66-8.63 (1H, m) , 8.40 (1H, d) , 8.28 (1H, s), 8.12-8.07 (1H, m) , 7.41 (1H, dd) , 6.81 (1H, d) , 1.33 (9H, s).
Production Example 6
N- [2-OXO-6- (pyridin-3-yl) -2H-pyran-3-yl ] - cyclopropanecarboxamide (hereinafter, referred to as the inventive compound 6) was obtained according to the method described in Production Example 1 using
(cyclopropylcarbonylamino) acetic acid instead of N- acetylglycine .
Figure imgf000182_0002
Inventive compound 6
1 H-NMR (CDCI3) δ: 9.02-9.00 (1H, m) , 8.65-8.62 (1H, 8.35 (1H, d) , 8.23 (1H, s), 8.08-8.04 (1H, m) , 7.41 (1H, m) , 6.81-6.78 (1H, m) , 1.65-1.59 (1H, m) , 1.13 (2H, m) , 0.96-0.91 (2H, m) .
Production Example 7 N- [2-OXO-6- (pyridin-3-yl ) -2H-pyran-3-yl ] - cyclobutanecarboxamide (hereinafter, referred to as the inventive compound 7) was obtained according to the method described in Production Example 1 using
( cyclobutylcarbonylamino ) acetic acid instead of N- acetylglycine.
Figure imgf000183_0001
Inventive compound 7
1 H-NMR (CDC13 ) δ: 9.02-9.00 (1H, m) , 8.65-8.63 (1H, m) , 8.42 (1H, d) , 8.08-8.04 (1H, m) , 7.89 (1H, s), 7.42-7.37 (1H, m) , 6.81 (1H, dd) , 3.28-3.19 (1H, m) , 2.44-2.34 (2H, m) , 2.31-2.22 (2H, m) , 2.11-2.00 ( 1H, m) , 1.99-1.90 (1H, m) .
Production Example 8
N- [2-OXO-6- ( pyridin-3-yl ) -2H-pyran-3-yl ] - cyclocyclopentanecarboxamide (hereinafter, referred to as the inventive compound 8) was obtained according to the method described in Production Example 1 using
( cyclopentylcarbonylamino ) acetic acid instead of N- acetylglycine .
Figure imgf000184_0001
Inventive compound 8
1 H-NMR (CDC13) δ: 9.02-9.00 (1H, m) , 8.65-8.63 (1H, m) , 8.40 (1H, d) , 8.08-8.04 (1H, m) , 8.02 (1H, s), 7.41-7.37 (1H, m) , 6.80 (1H, d) , 2.82-2.73 (1H, m) , 2.02-1.94 (2H, m) , 1.93-1.84 (2H, m) , 1.83-1.75 (2H, m) , 1.70-1.64 (2H, m) .
Production Example 9
N- [2-OXO-6- (pyridin-3-yl ) -2H-pyran-3-yl ] - cyclocyclohexanecarboxamide (hereinafter, referred to as the inventive compound 9) was obtained according to the method described in Production Example 1 using
( cyclohexylcarbonylamino ) acetic acid instead of N- acetylglycine.
Figure imgf000184_0002
Inventive compound 9
1 H-NMR (CDCI3) δ: 9.02-9.00 (1H, m) , 8.65-8.62 (1H, m) , 8.40 (1H, d) , 8.09-8.04 (1H, m) , 8.03 (1H, s), 7.39 (1H, dd), 6.80 (1H, d) , 2.36-2.27 (1H, m) , 1.97 (2H, d) , 1.88-1.82 (2H, m) , 1.72 (1H, d) , 1.58-1.47 (2H, m) , 1.39-1.23 (3H, m)
Production Example 10
N-[2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] -1- methylcyclohexanecarboxamide (hereinafter, referred to as the inventive compound 10) was obtained according to the method described in Production Example 1 using [(1- methylcyclohexane carbonyl ) -amino] -acetic acid instead of N-acetylglycine.
Figure imgf000185_0001
Inventive compound 10
1 H-NMR (CDC13) δ: 9.02-9.00 (1H, m) , 8.65-8.62 (1H, m) , 8.42 (1H, d) , 8.30 (1H, s), 8.09-8.05 (1H, m) , 7.42-7.37 (1H, m) , 6.81 (1H, d) , 2.06-1.99 (2H, m) , 1.71-1.67 (3H, m) , 1.66-1.59 (2H, m) , 1.52-1.43 (3H, m) , 1.27 (3H, s).
Production Example 11
N- [2-OXO-6- (pyridin-3-yl ) -2H-pyran-3-yl ] -2- methylcyclohexanecarboxamide (hereinafter, referred to as the inventive compound 11) was obtained according to the method described in Production Example 1 using [(2- methylcyclohexane carbonyl) -amino] -acetic acid instead of N-acetylglycine.
Figure imgf000186_0001
Inventive compound 11
1 H-NMR (CDC13) δ: 9.03-8.99 (1H, m) , 8.66-8.63 (1H, m) , 8.44 (1H, d) , 8.10-8.05 (1H, m),7.98 (1H, s), 7.40. (1H, dd) , 6.81 (1H, d) , 1.84-1.73 (8H, m) , 1.31-1.23 (2H, m) , 0.93 (3H, d) .
Production Example 12
N- [2-OXO-6- (pyridin-3-yl ) -2H-pyran-3-yl ] -3- methylcyclohexanecarboxamide (hereinafter, referred to as the inventive compound 12) was obtained according to the method described in Production Example 1 using [(3- methylcyclohexane carbonyl ) -amino ] -acetic acid instead of N-acetylglycine.
Figure imgf000186_0002
Inventive compound 12
1 H-NMR (CDCI3 ) δ: 9.02-9.00 (1H, m) , 8.65-8.63 (1H, m) ,
8.40 (1H, d) , 8.09-8.04 (1H, m) , 8.02 (1H, s), 7.42-7.37
(1H, m) , 6.80 (1H, d) , 2.38-2.30 (1H, m) , 1.99-1.91 (2H, m) , 1.89-1.84 (1H, m) , 1.76-1.69 (1H, m) , 1.49-1.39 (2H, m) , 1.38-1.28 (1H, m) , 1.23-1.13 (1H, m) , 1.08-0.90 (4H, m) .
Production Example 13
N- [2-OXO-6- ( pyridin-3-yl ) -2H-pyran-3-yl ] -4- methylcyclohexanecarboxamide (hereinafter, referred to as the inventive compound 13) was obtained according to the method described in Production Example 1 using [(4- methylcyclohexane carbonyl ) -amino ] -acetic acid instead of N-acetylglycine.
Figure imgf000187_0001
Inventive compound 13
1 H-NMR (CDC13 ) δ : 9.02-9.00 (1H, m) , 8.65-8.62 (1H, m) , 8.42-8.38 (1H, m) , 8.08-8.02 (2H, m) , 7.39 (1H, dd) , 6.80 (1H, d) , 2.29-2.20 (1H, m) , 2.02-1.95 (2H, m) , 1.86-1.79 (2H, m) , 1.62-1.49 (2H, m) , 1.46-1.36 (1H, m) , 1.05-0.95 (2H, m) , 0.94-0.90 (3H, m) .
Production Example 14
N- [2-OXO-6- (pyridin-3-yl ) -2H-pyran-3-yl ] -2-butenoic amide (hereinafter, referred to as the inventive
compound 14) was obtained according to the method described in Production Example 1 using (2- butenoylamino ) -acetic acid instead of N-acetylglycine.
Figure imgf000188_0001
Inventive compound 14
1 H-N R (CDC13) δ: 9.03-9.00 (1H, m) , 8.66-8.63 (1H, 8.46 (1H, d) , 8.09-8.05 (1H, m) , 7.98 (1H, s), 7.42 (1H, m) , 7.03 (1H, dt), 6.82 (1H, d) , 6.01 (1H, dd) 1.97-1.93 (3H, m) .
Production Example 15
N- [2-OXO-6- (pyridin-3-yl ) -2H-pyran-3-yl ] -4- methylbenzamide (hereinafter, referred to as the
inventive compound 15) was obtained according to the method described in Production Example 1 using (4- methylbenzoylamino ) -acetic acid instead of N- acetylglycine .
Figure imgf000188_0002
Inventive compound 15
1 H-NMR (CDCI3) δ: 9.05-9.03 (1H, m) , 8.74 (1H, s) , 8.67- 8.64 (1H, m) , 8.56 (1H, d) , 8.11-8.08 (1H, m) , 7.81 (2H, d) , 7.43-7.39 (1H, m) , 7.32 (2H, d) , 6.86 (1H, d) , 2.43 (3H, d) . Production Example 16
N- [2-OXO-6- (pyridin-3-yl) -2H-pyran-3-yl ] -4- nitrobenzamide (hereinafter, referred to as the
inventive compound 16) was obtained according to the method described in Production Example 1 using (4- nitrobenzoylamino ) -acetic acid instead of N- acetylglycine.
Figure imgf000189_0001
Inventive compound 16
1 H-NMR (DMSO-D6) δ: 10.23 (1H, s), 9.09-9.06 (1H, m) ,
8.69-8.65 (1H, m) , 8.39-8.35 (2H, m) , 8.27-8.23 (1H, m) , 8.23-8.21 (1H, m) , 8.17 (2H, d) , 7.59-7.54 (1H, m) , 7.33 (1H, d) .
Production Example 17
N- [2-OXO-6- (pyridin-3-yl) -2H-pyran-3-yl ] -nicotinic amide (hereinafter, referred to as the inventive
compound 17) was obtained according to the method described in Production Example 1 using nicotinoylamino- acetic acid instead of N-acetylglycine.
Figure imgf000190_0001
Inventive compound 17
1 H-NMR (CDC13) δ: 9.17-9.16 (1H, m) , 9.05-9.04 (1H, m) , 8.84-8.82 (1H, m),8.73 (1H, s), 8.67-8.66 (1H, m) , 8.55(1H, d) , 8.21-8.18 (1H, m) , 8.11-8.08 (1H, m) , 7.49 7.46 (1H, m) , 7.43-7.39 (1H, m) , 6.87 (1H, d) .
Production Example 18
N- [6- ( 2 -chloropyridin- 3-yl ) -2-oxo-2H-pyran-3-yl ] - acetamide (hereinafter, referred to as the inventive compound 18) was obtained according to the method described in Production Example 1 using l-(2-chloro- pyridin-3-yl ) -3-dimethylamino-propenone instead of 3- dimeth lamino-1- (pyridin-3-yl ) -propenone.
Figure imgf000190_0002
Inventive compound 18
1 H-NMR (CDCI3) δ: 8.47-8.44 (1H, m) , 8.40-8.37 (1H, m) , 8.07-8.02 (2H, m) , 7.40-7.36 (1H, m) , 7.04-7.01 (1H, m) 2.25 (3H, s) .
Production Example 19
N- [6- ( 6-chloropyridin-3-yl ) -2-oxo-2H-pyran-3-yl] - acetamide (hereinafter, referred to as the inventive compound 19) was obtained according to the method described in Production Example 1 using l-(6-chloro- pyridin-3-yl ) -3-dimethylamino-propenone instead of 3- dimeth lamino-1- (pyridin-3-yl ) -propenone..
Figure imgf000191_0001
Inventive compound 19
1 H-NMR (CDC13 ) δ: 8.77-8.76 (1H, m) , 8.37-8.35 (1H,
8.01-7.99 (1H, m) , 7.97 (1H, s), 7.42-7.40 (1H, m) , (1H, d) , 2.22 (3H, s) .
Production Example 20
N- [6- ( 6-methylpyridin-3-yl ) -2-oxo-2H-pyran-3-yl] - acetamide (hereinafter, referred to as the inventive compound 20) was obtained according to the method described in Production Example 1 using l-(6- methylpyridin-3-yl ) -3-dimethylamino-propenone instead 3-dimethylamino-l- (pyridin-3-yl) -propenone.
Figure imgf000191_0002
Inventive compound 20
1 H-NMR (CDCI3) δ: 8.88-8.87 (1H, m) , 8.37-8.35 (1H, 7.95-7.93 (2H, m) , 7.24-7.22 (1H, m) , 6.73 (1H, d) , (3H, s) , 2.20 (3H, s) . Production Example 21
N- [2-OXO-6- ( 4-trifluoromethylpyridin-3-yl ) 2H-pyran- 3-yl ] -cyclopropanecarboxamide (hereinafter, referred to as the inventive compound 21) was obtained according to the method described in Production Example 1 using 3- dimethylamino-1- ( 4-trifluoromethyl-pyridin-3-yl ) - propenone instead of 3-dimethylamino-l- (pyridin-3-yl ) - propenone, and using ( cyclopropylcarbonylamino) acetic acid instead of N-acetylglycine .
Figure imgf000192_0001
Inventive compound 21
1 H-NMR (CDC13) δ: 8.90-8.88 (2H, m) , 8.35-8.32 (1H, m) , 8.27-8.23 (1H, m) , 7.69-7.66 (1H, m) , 6.54-6.52 (1H, m) , 1.67-1.62 (1H, m) , 1.14-1.09 (2H, m) , 0.97-0.92 (2H, m) .
Production Example 22
N- [6- ( 5-bromopyridin-3-yl ) -2-oxo-2H-pyran-3-yl ] - acetamide (hereinafter, referred to as the inventive compound 22) was obtained according to the method described in Production Example 1 using l-(5- bromopyridin-3-yl ) -3-dimethylamino-propenone instead 3-dimethylamino-l- (pyridin-3-yl ) -propenone.
Figure imgf000193_0001
Inventive compound 22
1 H-NMR (CDC13) δ: 8.91-8.89 (1H, m) , 8.70-8.68 (1H, m) ,
8.38 (1H, d) , 8.23-8.21 (1H, m) , 8.01 (1H, s), 6.81 (1 (3H, s) . H, d) , 2.25
Production Examples 23 and 24
N- [6- ( 5-chloropyridin-3-yl ) -2-oxo-2H-pyran-3-yl] - acetamide (hereinafter, referred to as the inventive compound 23) and N-acetyl-N- [ 6- ( 5-chloropyridin-3-yl ) -2- oxo-2H-pyran-3-yl ] -acetamide (hereinafter, referred to as the inventive compound 24) were obtained according to the method described in Production Example 1 using l-(5- chloropyridin-3-yl ) -3-dimethylamino-propenone instead of 3-dimethylamino-l- (pyridin-3-yl ) -propenone .
Figure imgf000193_0002
Inventive compound 23
1 H-NMR (DMSO-D6) 5:9.85 (s, 1H), 8.96 (d, 1H) , 8.68 (d, 1H) , 8.30-8.28 (m, 1H) , 8.25 (d, 1H) , 7.34 (d, 1H) , 2.16 (s, 3H) .
Figure imgf000194_0001
Inventive compound 24
1 H-NMR (DMSO-D6) δ: 9.07 (d, 1H) , 8.79 (d, 1H) , 8.44- 8.42 (m, 1H) , 7.94 (d, 1H) , 7.45 (d, 1H) , 2.31 (s, 6H)
Production Example 25
N- [6- (5, 6-dichloropyridin-3-yl ) -2-oxo-2H-pyran-3- yl ] -acetamide (hereinafter, referred to as the inventive compound 25) was obtained according to the method described in Production Example 1 using l-(5,6- dichloropyridin-3-yl ) -3-dimethylamino-propenone instead of 3-dimethylamino-l- (pyridin-3-yl) -propenone .
Figure imgf000194_0002
Inventive compound 25
1 H-NMR (DMSO-D6) δ: 9.87 (s, 1H) , 8.80 (d, 1H), 8.49 (d, 1H), 8.25 (d, 1H) , 7.35 (d, 1H) , 2.16 (s, 3H)
Production Example 26
N- [6- ( 5-phenylpyridin- 3-yl ) -2-oxo-2H-pyran-3-yl ] - acetamide (hereinafter, referred to as the inventive compound 26) was obtained according to the method described in Production Example 1 using l-(5- phenylpyridin-3-yl ) -3-dimethylamino-propenone instead of 3-dimeth lamino-l- (pyridin-3-yl ) -propenone.
Figure imgf000195_0001
Inventive compound 26
1 H-NMR (CDC13) δ: 8.97-8.96 (1H, m) , 8.87-8.85 (1H, m) , 8.41 (1H, d) , 8.24-8.22 (1H, m) , 8.02 (1H, s), 7.64-7.62 (2H, m) , 7.54-7.49 (2H, m) , 7.48-7.43 (1H, m) , 6.87 (1H, d) , 2.25 (3H, s) .
Production Example 27
N- [5-methyl-2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ) ] - acetamide (hereinafter, referred to as the inventive compound 27) was obtained according to the method described in Production Example 1 using 3-dimethylamino- 2-methyl-l-pyridin-3-ylpropenone instead of 3- dimethylamino-1- (pyridin-3-yl ) -propenone.
Figure imgf000195_0002
Inventive compound 27
1 H-NMR (CDCI3) δ: 8.82-8.79 (1H, m) , 8.67-8.64 (1H, m) , 8.29-8.27 (1H, m) , 8.00 (1H, s), 7.91-7.87 (1H, m) , 7.43-7.38 (1H, m) , 2.25-2.22 (6H, m) .
Production Example 28
5-acetylamino-6-oxo-2- (pyridin-3-yl ) -6H-pyran-3- carboxylic acid methyl ester (hereinafter, referred to as the inventive compound 28) was obtained according to the method described in Production Example 1 using 3- dimethylamino-2- (pyridin-3-carbonyl ) -acrylic acid methyl ester instead of 3-dimethylamino- 1- (pyridin-3-yl ) - propenone .
Figure imgf000196_0001
Inventive compound 28
1 H-NMR (CDC13) δ: 8.77-8.74 (1H, m) , 8.74 (1H, s), 8.72-
8.70 (1H, m) , 7.91 (1H, s), 7.91-7.87 (1H, m) , 7.42-7.40
(1H, m) , 3.77 (3H, s), 2.26 (3H, s).
Production Example 29
N-acetyl-N- [ 4 -methyl-2 -oxo- 6- (pyridin-3-yl ) -2H- pyran-3-yl ] -acetamide (hereinafter, referred to as the inventive compound 29) was obtained according to the method described in Production Example 1 using 3- dimethylamino-1- (pyridyl-3-yl ) -2-buten-l-one instead of 3-dimethylamino-l- (pyridin-3-yl ) -propenone. ,
Figure imgf000196_0002
Inventive compound 29
1 H-NMR (DMSO-D6) δ: 9.12 (s, 1H) , 8.72 (d, 1H) , 8.28 (d, 1H) , 7.59 (dd, 1H) , 7.39 (s, 1H) , 2.31 (s, 6H) , 2.14 (s,
3H)
Production Example 30
A mixture of 10.0 g of N- [2-oxo-6- (pyridin-3-yl ) -2H- pyran-3-yl ] -acetamide , 30.0 g of a boron trifluoride
( 63% ) -methanol solution and 150 ml of methanol was stirred for 8 hours under reflux with heat. After cooling down to room temperature, the precipitate was filtrated. The resultant precipitate was added to 300 ml of a potassium carbonate aqueous solution (potassium carbonate 18.0 g) , and the mixture was stirred for 0.5 hours at room temperature. The precipitate was
filtrated and washed with 100 ml of water, then, dried under reduced pressure to obtain 7.3 g of 3-amino-6-
(pyridin-3-yl ) -pyran-2-one (hereinafter, referred to as the inventive compound 30).
Figure imgf000197_0001
Inventive compound 30
1 H-NMR (DMSO-D6) δ: 8.91-8.89 (1H, m) , 8.51-8.48 (1H, m) , 8.02 (1H, d) , 7.45 (1H, dd) , 7.05 (1H, d) , 6.43 (1H, d) , 5.77 (2H, s) .
1 H-NMR (CDC13) δ: 8.94-8.92 (1H, m) , 8.56-8.54 (1H, m) , 8.02-8.00 (1H, m) , 7.36-7.32 (1H, m) , 6.66 (1H, d) , 6.45 (1H, d) , 4.29 (2H, s) .
Production Example 31 To a mixture of 0.5 g of 3-amino-6- (pyridin-3-yl ) - pyran-2-one and 20 ml of THF was added 0.27 g of
acryloyl chloride and 0.35 g of triethylamine at 0°C, and the mixture was stirred for 18 hours at room
temperature. To the reaction mixture was added 10 ml of water, and about 15 ml of THF was distilled off under reduced pressure, and the precipitate was filtrated.
The filtrated precipitate was washed with 10 ml of water and 15 ml of hexane, then, drying under reduced pressure was performed to obtain 0.24 g of N- [ 2-oxo-6- (pyridin-3- yl ) -2H-pyran-3-yl ] -acrylamide (hereinafter, referred to as the inventive compound 31).
Figure imgf000198_0001
Inventive compound 31
1 H-NMR (DMSO-D6) δ: 10.05 (1H, s), 9.05-9.02 (1H, m) ,
8.65-8.62 (1H, m) , 8.40 (1H, d) , 8.21-8.17 (1H, ,m) , 7.54 (1H, dd) , 7.28 (1H, d) , 6.84 (1H, dd) , 6.32-6.25 (1H, m) , 5.80-5.76 ( 1H, m) . Production Example 32
N- [2-OXO-6- (pyridin-3-yl ) -2H-pyran-3-yl ] -3-methyl- butylamide (hereinafter, referred to as the inventive compound 32) was obtained according to the method described in Production Example 31 using 3-methyl- butyryl chloride instead of acryloyl chloride.
Figure imgf000199_0001
Inventive compound 32
1 H-NMR (CDCI3 ) δ: 9.02-9.00 (1H, m) , 8.66-8.63 (1H, m) ,
8.42 (1H, d) , 8.08-8.04 (1H, m) , 7.97 (1H, s), 7.42-7.37
(1H, m) , 6.80 (1H, d) , 2.30 (2H, d) , 2.26-2.15 (1H, m) , 1.02 (6H, d) .
Production Example 33
N- [2-OXO-6- (pyridin-3-yl) -2H-pyran-3-yl ] -2- phenylacetamide (hereinafter, referred to as the
inventive compound 33) was obtained according to the method described in Production Example 31 using
henylacetyl chloride instead of acryloyl chloride.
Figure imgf000199_0002
Inventive compound 33
1 H-NMR (CDCI3) δ: 9.00-8.98 (1H, m) , 8.64-8.62 (1H, 8.38 (1H, dd) , 8.06-8.02 (2H, m) , 7.43-7.37 (3H, m) 7.37-7.32 (3H, m) , 6.78 (1H, d) , 3.77 (2H, s). Production Example 34
N- [2-OXO-6- (pyridin-3-yl) -2H-pyran-3-yl ] -2- methylbutylamide (hereinafter, referred to as the inventive compound 34) was obtained according to the method described in Production Example 31 using 2- methylbutyryl chloride instead of acryloyl chloride.
Figure imgf000200_0001
Inventive compound 34
1 H-NMR (CDC13) δ: 9.02-9.00 (1H, m) , 8.66-8.63 (1H, m) , 8.43 (1H, d) , 8.08-8.05 (1H, m) , 8.00 (1H, s), 7.39 (1H, dd) , 6.81 (1H, d) , 2.37 (1H, td) , 1.83-1.72 (1H, m) , 1.59-1.49 (1H, m) , 1.24 (3H, d) , 0.97 (3H, t).
Production Example 35
N- [2-OXO-6- (pyridin-3-yl ) -2H-pyran-3-yl ] -pentanoic acid amide (hereinafter, referred to as the inventive compound 35) was obtained according to the method described in Production Example 31 using pentanoyl chloride instead of acryloyl chloride.
Figure imgf000200_0002
Inventive compound 35
1 H-NMR (CDCI3) δ: 9.03-9.00 (1H, m) , 8.67-8.63 (1H, m) , 8.40 (1H, d) , 8.08-8.05 (1H, m) , 7.98 (1H, s), 7.39 (1H, dd) , 6.80 (1H, d) , 2.43 (2H, t), 1.75-1.68 (2H, m) , 1.47-1.36 (2H, m) , 0.96 (3H, t). Production Example 36
N- [2-OXO-6- (pyridin-3-yl) -2H-pyran-3-yl ] -4- bromobutylamide (hereinafter, referred to as the
inventive compound 36) was obtained according to the method described in Production Example 31 using 4- bromobut ryl chloride instead of acryloyl chloride.
Figure imgf000201_0001
Inventive compound 36
1 H-NMR (CDC13) δ: 9.03-9.00 (1H, m) , 8.67-8.63 (1H, m) ,
8.38 (1H, d) , 8.09-8.04 (2H, m) , 7.40 (1H, dd) , 6.81
(1H, d) , 3.53 (2H, t ) , 2.65 (2H, t), 2.32-2.25 (2H, m) .
Production Example 37
N- [2-OXO-6- (pyridin-3-yl) -2H-pyran-3-yl ] -5-bromo- pentanoic acid amide (hereinafter, referred to as the inventive compound 37) was obtained according to the method described in Production Example 31 using 5-bromo- entanoyl chloride instead of acryloyl chloride.
Figure imgf000201_0002
Inventive compound 37
1 H-NMR (CDCI3) δ: 9.02-9.00 (1H, m) , 8.66-8.63 (1H, m) , 8.39 (1H, d) , 8.08-8.05 (1H, m) , 7.99 (1H, s), 7.40 (1H, dd) , 6.81 (1H, d) , 3.45 (2H, t), 2.48 (2H, t), 2.00-1.86 (4H, m) .
Production Example 38
N- [2-OXO-6- (pyridin-3-yl) -2H-pyran-3-yl ] -2- chloroacetamide (hereinafter, referred to as the
inventive compound 38) was obtained according to the method described in Production Example 31 using
chloroacet l chloride instead of acryloyl chloride.
Figure imgf000202_0001
Inventive compound 38
1 H-NMR (D SO-D6) δ: 10.21 (1H, s), 9.11-9.09 (1H, m) , 8.72-8.70 (1H, m) , 8.35 (1H, d) , 8.29 (1H, d) , 7.69 (1H, dd) , 7.34 (1H, d) , 4.47 (2H, s) .
Production Example 39
N- [2-OXO-6- (pyridin-3-yl ) -2H-pyran-3-yl ] -5- methylhexanoic acid amide (hereinafter, referred to as the inventive compound 39) was obtained according to the method described in Production Example 31 using 5- meth lhexanoyl chloride instead of acryloyl chloride.
Figure imgf000202_0002
Inventive compound 39
1 H-NMR (CDC13) δ: 9.03-9.00 (1H, m) , 8.66-8.63 (1H, m) , 8.40 (1H, d) , 8.08-8.05 (1H, m) , 7.97 (1H, s), 7.39 (1H, dd) , 6.80 (1H, d) , 2.41 (2H, t), 1.77-1.69 (2H, m) , 1.59-1.56 (1H, m) , 1.28-1.23 (2H, m) , 0.91 (6H, d) .
Production Example 40
N- [2-OXO-6- (pyridin-3-yl) -2H-pyran-3-yl ] -2- cyclopropylacetamide (hereinafter, referred to as the inventive compound 40) was obtained according to the method described in Production Example 31 using
c clopropylacetyl chloride instead of acryloyl chloride.
Figure imgf000203_0001
Inventive compound 40
1 H-NMR (CDC13) δ : 9.03-9.01 (1H, m) , 8.66-8.63 (1H, m) , 8.41 (1H, d) , 8.09-8.05 (1H, m) , 7.40 (1H, dd) , 6.81 (1H, d) , 2.37 (2H, d) , 1.13-1.06 (1H, m) , 0.77-0.73 (2H, m) , 0.33-0.29 (2H, m) .
Production Example 41
N- [2-OXO-6- (pyridin-3-yl ) -2H-pyran-3-yl ] -4-pentenoic acid amide (hereinafter, referred to as the inventive compound 41) was obtained according to the method described in Production Example 31 using 4-pentenoyl chloride instead of acryloyl chloride.
Figure imgf000204_0001
Inventive compound 41
1 H-NMR (CDC13) δ: 9.02 (1H, s), 8.65 (1H, s), 8.40 (1H, d) , 8.07 (lHf d) , 8.01 (1H, s), 7.41-7.39 (1H, m) , 6.80
(1H, d) , 5.92-5.82 (1H, m) , 5.16-5.06 (2H, m) , 2.56-2.48
(4H, m) .
Production Example 42
N- [2-OXO-6- (pyridin-3-yl ) -2H-pyran-3-yl ] -2- methylpentanoic acid amide (hereinafter, referred to as the inventive compound 42) was obtained according to the method described in Production Example 31 using 2- methylpentanoyl chloride instead of acryloyl chloride.
Figure imgf000204_0002
Inventive compound 42
1 H-NMR (DMSO-D6) δ: 9.68 (1H, s), 9.03-9.01 (1H, m) , 8.64-8.62 (1H, m) , 8.28 (1H, d) , 8.19-8.15 (1H, m) , 7.53 (1H, dd) , 7.24 (1H, d) , 2.91-2.84 (1H, m) , 1.60-1.52 (1H, m) , 1.34-1.21 (3H, m) , 1.07-1.04 (3H, m) , 0.87 (3H, t) .
Production Example 43 N- [2-OXO-6- (pyridin-3-yl ) -2H-pyran-3-yl ] -furan-2- carboxamide (hereinafter, referred to as the inventive compound 43) was obtained according to the method described in Production Example 31 using furan-2- carbonyl chloride instead of acryloyl chloride.
Figure imgf000205_0001
Inventive compound 43
1 H-NMR (DMSO-D6) δ: 9.27 (1H, s), 9.07-9.05 (1H, m) , 8.68-8.65 (1H, m) , 8.24-8.21 (2H, m) , 8.01-7.99 (1H, m) 7.58 (1H, dd) , 7.44-7.42 (1H, m) , 7.33 (1H, d) , 6.76- 6.74 (1H, m) .
Production Example 44
N- [2-OXO-6- (pyridin-3-yl ) -2H-pyran-3-yl ] -thiophen-2 carboxamide (hereinafter, referred to as the inventive compound 44) was obtained according to the method described in Production Example 31 using thiophen-2- carbonyl chloride instead of acryloyl chloride.
Figure imgf000205_0002
Inventive compound 44
-N R (D SO-D6) δ: 9.78 (1H, s), 9.07-9.06 (1H, 8.67-8.65 (1H, m) , 8.24-8.20 (1H, m) , 8.13 (1H, d) , 8.11-8.09 (1H, m) , 7.93-7.91 (1H, m) , 7.56 (1H, dd) , 7.31 (1H, d) , 7.25-7.22 (1H, m) .
Production Example 45
N- [2-OXO-6- (pyridin-3-yl ) -2H-pyran-3-yl ] -2-fluoro- benzamide (hereinafter, referred to as the inventive compound 45) (0.50 g) was obtained according to the method described in Production Example 31 using 2- fluorobenzo l chloride instead of acryloyl chloride.
Figure imgf000206_0001
Inventive compound 45
1 H-NMR (DMSO-D6) δ : 9.84-9.80 (1H, m) , 9.06-9.04 (1H, m) , 8.65 (1H, t ) , 8.40-8.36 (1H, m) , 8.20 (1H, t), 7.89 7.84 (1H, m) , 7.68-7.60 (1H, m) , 7.58-7.53 (1H, m) , 7.44-7.36 (2H, m) , 7.34-7.27 (1H, m) .
Production Example 46
N- [2-OXO-6- (pyridin-3-yl) -2H-pyran-3-yl ] -2- methoxybenzamide (hereinafter, referred to as the inventive compound 46) was obtained according to the method described in Production Example 31 using 2- methoxybenzoyl chloride instead of acryloyl chloride.
Figure imgf000207_0001
Inventive compound 46
1 H-NMR (DMSO-D6) δ: 10.76 (1H, s), 9.05-9.03 (1H, m) ,
8.65-8.62 (1H, m) , 8.43 (1H, d) , 8.20-8.16 (1H, m) ,
8.09-8.06 (1H, m) , 7.66-7.61 (1H, m) , 7.57-7.52 (1H,
7.34-7.29 (2H, m) , 7.20-7.15 (1H, m) , 4.07 (3H, d) .
Production. Example 47
N- [2-OXO-6- (pyridin-3-yl) -2H-pyran-3-yl ] -2- methoxyacetamide (hereinafter, referred to as the inventive compound 47) was obtained according to the method described in Production Example 31 using
methox acetyl chloride instead of acryloyl chloride.
Figure imgf000207_0002
Inventive compound 47
1 H-NMR (CDC13) δ: 9.02 (1H, s), 8.65 (1H, d) , 8.42 (1H, d) , 8.12-8.08 (1H, m) , 7.41 (1H, dd) , 6.80 (1H, d) , 4.05 (2H, s) , 3.52 (3H, s) .
Production Example 48
N- [2-OXO-6- (pyridin-3-yl) -2H-pyran-3-yl ] -3
methoxypropionamide (hereinafter, referred to inventive compound 48) was obtained according to the method described in Production Example 31 using 3- methoxy-propionyl chloride instead of acryloyl chloride.
Figure imgf000208_0001
Inventive compound 48
1 H-N R (CDC13) δ: 9.04 (1H, s), 9.01 (1H, s), 8.66-8.62
(1H, m) , 8.38 (1H, d) , 8.08-8.04 (1H, m) , 7.39 (1H, dd) ,
6.78 (1H, d) , 3.73 (2H, t), 3.48 (3H, s), 2.68 (2H, t). Production Example 49
To a mixture of 0.7 g of tetrahydrofuran-2 - carboxylic acid and 10 ml of THF was added 0.84 g of oxalyl chloride and 0.05 ml of DMF. The mixture was stirred for 2 hours at room temperature, then, THF was distilled off under reduced pressure. To the residue was added 20 ml of THF and 1.02 g of 3-amino-6- (pyridin- 3-yl ) -pyran-2-one , then, 0.91 g of triethylamine was added, and the mixture was stirred for 18 hours at room temperature. Water (10 ml) was added, and about 15 ml of THF was distilled off under reduced pressure, then, the precipitate was filtrated. The filtrated
precipitate was washed with 10 ml of water and 15 ml of hexane, then, drying under reduced pressure was
performed to obtain 0.88 g of N- [2-oxo-6- (pyridin-3-yl) - 2H-pyran-3-yl ] -tetrahydrofuran-2-carboxamide
(hereinafter, referred to as the inventive compound 49) .
Figure imgf000209_0001
Inventive compound 49
1 H-NMR (CDC13) δ: 9.19 (1H, s), 9.03-9.00 (1H, m) , 8.66- 8.63 (1H, m) , 8.42 (1H, d) , 8.10-8.06 (1H, m) , 7.40 (1H, dd) , 6.79 (1H, d) , 4.48 (1H, dd) , 4.14-4.08 (1H, m) , 4.00-3.95 (1H, m) , 2.42-2.32 (1H, m) , 2.19-2.10 (1H, m) , 2.02-1.91 (2H, m) .
Production Example 50
[2-OXO-6- (pyridin-3-yl ) -2H-pyran-3-yl ] - tetrahydrofuran-3-carboxamide (hereinafter, referred to as the inventive compound 50) was obtained according to the method described in Production Example 49 using tetrahydrofuran-3-carboxylic acid instead of
tetrahydrofuran-2-carboxylie acid .
Figure imgf000209_0002
Inventive compound 50
1 H-NMR (CDCI3 ) δ: 9.02-9.00 (1H, m) , 8.66-8.64 (1H, m) , 8.39 (1H, d) , 8.19 (1H, s), 8.08-8.05 (1H, m) , 7.40 (1H, dd) , 6.81 (1H, d) , 4.05-3.99 (3H, m) , 3.90-3.85 (1H, m) , 3.17-3.10 (1H, m) , 2.27 (2H, q) . Production Example 51
N- [2-OXO-6- (pyridin-3-yl ) -2H-pyran-3-yl ] -3, 3, 3- trifluoropro-pionamide (hereinafter, referred to as the inventive compound 51) was obtained according to the method described in Production Example 49 using 3,3,3- trifluoro-propionic acid instead of tetrahydrofuran-2- carbox lic acid.
Figure imgf000210_0001
Inventive compound 51
1 H-NMR (DMSO-D6) δ: 10.23 (1H, s), 9.04-9.01 (1H, m) , 8.65-8.62 (1H, m) , 8.28 (1H, d) , 8.20-8.17 (1H, m) , 7.54 (1H, dd), 7.26 (1H, d) , 3.76 (2H, q) .
Production Example 52
To a mixture of 1.2 g of 3-amino-6- (pyridin-3-yl ) - pyran-2-one and 60 ml of THF was added 1.3 g of
trifluoroacetic anhydride and 1.1 g of pyridine, and the mixture was stirred for 18 hours at room temperature. Water (40 ml) was added, and about 30 ml of THF was distilled off under reduced pressure. The precipitate was filtrated, and the filtrated precipitate was washed with 20 ml of water and 25 ml of hexane, then, drying under reduced pressure was performed to obtain 1.6 g of N- [2-OXO-6- (pyridin-3-yl) -2H-pyran-3-yl ] -2,2,2- trifluoro-acetamide (hereinafter, referred to as the inventive compound 52) .
Figure imgf000211_0001
Inventive compound 52
1 H-N R (DMSO-D6) δ: 11.13 (1H, s), 9.07-9.06 (1H, m) , 8.68-8.66 (1H, m) , 8.24-8.21 (1H, m) , 7.99 (1H, d) , 7.56 (1H, dd) , 7.30 (1H, d) .
1 H-NMR (CDC13) δ: 9.07-9.04 (1H, m) , 8.72-8.69 (2H, m) , 8.42 (1H, d) , 8.13 (1H, d) , 7.46 (1H, dd) , 6.87 (1H, d) .
Production Example 53
N- [2-oxo- 6- (pyridin-3-yl) -2H-pyran-3-yl ] -2,2,3,3,3- pentafluoro-propionamide (hereinafter, referred to as the inventive compound 53) was obtained according to the method described in Production Example 52 using
2 , 2 , 3 , 3 , 3-pentafluoro-propionic anhydride instead of trifluoroacetic anhydride.
Figure imgf000211_0002
Inventive compound 53
1 H-NMR (DMSO-D6) δ: 11.14 (1H, s), 9.08 (1H,
8.67 (1H, m) , 8.25-8.21 (1H, m) , 7.93 (1H, d)
dd) , 7.29. (1H, d) . Production Example 54
N- [2-OXO-6- (pyridin-3-yl ) -2H-pyran-3-yl ] - methanesulfoneamide (hereinafter, referred to as the inventive compound 54) was obtained according to the method described in Production Example 52 using
methanesulfonic anhydride instead of trifluoroacetic anhydride .
Figure imgf000212_0001
Inventive compound 54
1 H-NMR (DMSO-D6) δ: 9.63 (1H, s), 9.05-9.04 (1H, m) , 8.68-8.65 (1H, m) , 8.24-8.20 (1H, m) , 7.58 (1H, dd) , 7.47 (1H, d) , 7.23 (1H, d) , 3.16 (3H, s). Production Example 55
To a mixture of 0.5 g of 3-amino-6- (pyridin-3-yl ) - pyran-2-one and 10 ml of pyridine was added 0.28 g of methyl chlorocarbonate, and the mixture was stirred for 10 hours at room temperature. To the reaction mixture was added 10 ml of water, and about 8 ml of pyridine was distilled off under reduced pressure. The precipitate was filtrated, and the filtrated precipitate was washed with 15 ml of water and 20 ml of hexane, then, drying under reduced pressure was performed to obtain 0.31 g of N- [2-ΟΧΟ-6- (pyridin-3-yl) -2H-pyran-3-yl] -carbamic acid methyl ester (hereinafter, referred to as the inventive com ound 55 ) .
Figure imgf000213_0001
Inventive compound 55
1 H-NMR (CDC13) δ: 9.01-9.00 (1H, m) , 8.65-8.62 (1H, m) , 8.07-8.02 (2H, m) , 7.50 (1H, br s), 7.39 (lH, dd) , 6.80 (1H, d) , 3.82 (3H, s) .
Production Example 56
N- [2-OXO-6- (pyridin-3-yl ) -2H-pyran-3-yl ] -carbamic acid ethyl ester (hereinafter, referred to as the inventive compound 56) was obtained according to the method described in Production Example 55 using ethyl chlorocarbonate instead of methyl chlorocarbonate.
Figure imgf000213_0002
Inventive compound 56
1 H-NMR (CDCI3 ) δ: 9.01-8.99 (1H, m) , 8.64-8.62 (1H, m) , 8.07-8.04 (1H, m) , 8.02 (1H, d) , 7.46 (1H, br s), 7.38 (1H, dd) , 6.80 (1H, d) , 4.26 (2H, q) , 1.33 (3H, t).
Production Example 57
To 4 ml of pyridine was added 0.3 g of 3-amino-6- (pyridin-3-yl ) -pyran-2 -one , and 0.38 g of phenyl chlorocarbonate was added under ice cool, and the
mixture was stirred for 20 hours at room temperature. The mixture was poured into water, and the precipitate was filtrated. The resultant filtrated product was washed with water and t-butyl methyl ether, then, dried under reduced pressure to obtain 0.22 g of N-[2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] -carbamic acid phenyl ester (hereinafter, referred to as the inventive compound 57) .
Figure imgf000214_0001
Inventive compound 57
1 H-NMR (DMSO-D6) δ : 9.86 (s, 1H) , 9.04 (s, 1H), 8.65 (d, 1H), 8.19 (d, 1H), 7.90 (d, 1H), 7.55 (dd, 1H) , 7.47- 7.42 (m, 2H) , 7.30-7.21 (m, 4H) .
Production Example 58
A mixture of 1.0 g of 3-amino- 6- (pyridin-3-yl ) - pyran-2-one and 15 ml of 2-chloroethy chlorocarbonate was stirred for 2 hours at 100°C. After cooling down to room temperature, the precipitate was filtrated, and the filtrated precipitate was washed with 20 ml of hexane, then, drying under reduced pressure was performed to obtain 1.4 g of N- [ 2-oxo-6- (pyridin-3-yl ) -2H-pyran-3- yl] -carbamic acid 2-chloro-ethyl ester hydrochloride (hereinafter, referred to as the inventive compound 58) .
Figure imgf000215_0001
Inventive compound 58
1 H-NMR (DMSO-D6) δ: 9.39 (1H, s), 9.12-9.10 (1H, m) , 8.74-8.72 (1H, m) , 8.41 (1H, d) , 7.88 (1H, d) , 7.74 (1H, dd) , 7.34 (1H, d) , 4.38 (2H, t), 3.87 (2H, t).
Production Example 59
To 0.16 g of sodium carbonate was added water until the total amount thereof reached 30 ml. To this was added 1.4 g of N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] - carbamic acid 2 -chloro-ethyl ester hydrochloride and the mixture was stirred for 2 hours at room temperature.
The precipitate was filtrated, and the filtrated
precipitate was washed with 30 ml of water and 20 ml of hexane, then, drying under reduced pressure was
performed to obtain 0.87 g of N- [ 2-oxo- 6- (pyridin-3-yl ) - 2H-pyran-3-yl ] -carbamic acid-2 -chloro-ethyl ester
(hereinafter, referred to as the inventive compound 59) .
Figure imgf000215_0002
Inventive compound 59
1 H-NMR (DMSO-D6) δ: 9.31 (1H, s), 9.03-9.01 (1H, m
8.64-8.62 (1H, m) , 8.19-8.15 (1H, m) , 7.86 (1H, d)
(1H, dd) , 7.25 (1H, d) , 4.38 (2H, t), 3.87 (2H, t) Production Example 60
As mixture of 1.0 g of 3-amino-6- (pyridin-3-yl ) - pyran-2-one and 15 ml of chloroethyl isocyanate was stirred for 2 hours at 100°C. After cooling down to room temperature, the precipitate was filtrated, and the filtrated precipitate was washed with 20 ml of hexane, then, drying under reduced pressure was performed to obtain 1.4 g of 1- ( 2-chloroethyl ) -3- [ 2-oxo- 6- (pyridin-3- yl ) -2H-pyran-3-yl ] -urea (hereinafter, referred to as the inventive compound 60) .
Figure imgf000216_0001
Inventive compound 60
1 H-NMR (DMSO-D6) δ: 9.09-9.07 (1H, m) , 8.83 (1H, s), 8.71-8.69 (1H, m) , 8.41-8.37 (1H, m) , 8.06-8.03 (1H, m) , 7.74 (1H, dd) , 7.44-7.40 (1H, m) , 7.33 (1H, d) , 3.69- 3.65 (2H, m) , 3.47-3.42 (2H, m) .
Production Example 61
To a mixture of 1.7 g of N- [ 2-oxo- 6- ( pyridin-3-yl ) -
2H-pyran-3-yl] - 4 -bromo-butylamide , 30 ml of THF and 3 ml of DMF was added 0.23 g of 55% sodium hydride (oily) at room temperature, and the mixture was stirred for 5 hours. Water (10 ml) was added, and the reaction mixture was extracted three times with ethyl acetate, and the combined organic layers were washed with
saturated saline, and dried over magnesium sulfate.
After performing filtration, the filtrate was
concentrated under reduced pressure. The residue was subjected to silica gel chromatography to obtain 0.70 of 1- [2-OXO-6- (pyridin-3-yl ) -2H-pyran-3-yl ] -pyrrolidin 2-one (hereinafter, referred to as the inventive
com ound 61 ) .
Figure imgf000217_0001
Inventive compound 61
1 H-NMR (CDC13) δ: 9.04-9.02 (1H, m) , 8.69-8.66 (1H, m) , 8.12-8.08 (1H, m) , 7.75 (1H, d) , 7.43-7.39 (1H, m) , 6.80 (1H, d) , 4.01 (2H, t), 2.58-2.54 (2H, m) , 2.22-2.13 (2H, m) .
Production Example 62
1- [2-OXO-6- ( pyridin-3-yl ) -2H-pyran-3-yl ] -piperidin- 2-one (hereinafter, referred to as the inventive
compound 62) was obtained according to the method described in Production Example 61 using [2-oxo-6-
(pyridin-3-yl ) -2H-pyran-3-y1 ] - 5-bromo-pentanoic acid amide instead of N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran-3- yl] -4-bromo-butylamide .
Figure imgf000218_0001
Inventive compound 62
1 H-NMR (CDC13) δ: 9.04-9.02 (1H, m) , 8.69-8.68 (1H, m) , 8.14-8.11 (1H, m) , 7.45 (1H, d) , 7.43-7.40 (1H, m) , 6.76 (1H, d) , 3.64-3.60 (2H, m) , 2.57 (2H, t), 1.98-1.94 (4H, m) .
Production Example 63
To a mixture of 1.7 g of N- [ 2-oxo- 6- ( pyridin- 3-yl ) - 2H-pyran-3-yl ] -carbamic acid 2 -chloro-ethyl ester, 30 ml of THF and 3 ml of DMF was added 0.23 g of 55% sodium hydride (oily) at room temperature, and the mixture was stirred for 5 hours. Water (10 ml) was added, and the reaction mixture was extracted three times with ethyl acetate, and the combined organic layers were washed with saturated saline, and dried over magnesium sulfate. After performing filtration, the filtrate was
concentrated under reduced pressure. The residue was subjected to silica gel chromatography to obtain 0.70 g of 1- [2-OXO-6- (pyridin-3-yl ) -2H-pyran-3-yl ] -pyrrolidin- 2-one (hereinafter, referred to as the inventive
compound 63 ) .
Figure imgf000218_0002
Inventive compound 63
1 H-NMR (D SO-D6) δ : 9.07 (1H, s), 8.70-8.67 (1H, m) , 8.25-8.21 (1H, m) , 7.83 (1H, d) , 7.57 (1H, dd) , 7.31 (1H, d) , 4.45 (2H, t), 4.05 (2H, t).
Production Example 64
To a mixture of 1.0 g of 1- (2-chloroethyl ) -3- [2-oxo- 6- (pyridin-3-yl) -2H-pyran-3-yl] -urea, 10 ml of THF and 10 ml of DMF was added 0.26 g of 55% sodium hydride (oily) at room temperature, and the mixture was stirred for 8 hours. Water (10 ml) was added, and the reaction mixture was extracted three times with ethyl acetate, and the combined organic layers were washed with
saturated saline, and dried over magnesium sulfate.
After performing filtration, the filtrate was
concentrated under reduced pressure. The residue was subjected to silica gel chromatography to obtain 0.10 g of 1- [2-OXO-6- (pyridin-3-yl ) -2H-pyran-3-yl ] - imidazolidin-2-one (hereinafter, referred to as the inventive com ound 64) .
Figure imgf000219_0001
Inventive compound
1 H-NMR (CDC13) δ : 9.00-8.99 (1H, m) , 8.64-8.62 (1H, 8.07-8.05 (1H, m) , 7.80 (1H, d) , 7.37 (1H, dd) , 6.76 (1H, d) , 4.70 (1H, s), 4.20 (2H, t), 3.56 (2H, t). Production Example 65
A mixture of 0.34 g of N- [ 2 -oxo- 6- (pyridin-3-yl ) -2H- pyran-3-yl ] -succinamic acid, 0.14 g of sodium acetate and 4 ml of acetic anhydride was stirred for 1 hour at 80°C. After cooling down to room temperature, 10 ml of water was added, and sodium carbonate was added
portionwise to adjust pH of the mixture to about 6. The mixture was allowed to stand for 6 hours, and the deposited precipitate was filtrated. The filtrated precipitate was washed with 10 ml of water and 10 ml of hexane, and drying under reduced pressure was performed to obtain 0.18 g of 1- [ 2-oxo-6- (pyridin-3-yl ) -2H-pyran- 3-yl ] -pyrrolidin-2 , 5-dione (hereinafter, referred to as the inventive compound 65) .
Figure imgf000220_0001
Inventive compound 65
1 H-NMR (DMSO-D6) δ: 9.12-9.10 (1H, m) , 8.72 (1H, d) , 8.29-8.26 (1H, m) , 7.79 (1H, d) , 7.59 (1H, dd) , 7.37 (1H, d) , 2.95-2.78 (4H, m) .
Production Example 66
1- [2-OXO-6- (pyridin-3-yl ) -2H-pyran-3-yl ] -piperidin- 2,6-dione (hereinafter, referred to as the inventive compound 66) was obtained according to the method described in Production Example 65 using 4-[2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-ylcarbamoyl ] -butyryl acid instead of 4 - [ 2 -oxo- 6- (pyridin-3-yl ) -2H-pyran-3-yl ] - succinamic acid.
Figure imgf000221_0001
Inventive compound 66
1 H-N R (DMSO-D6) δ: 9.10 (1H, s), 8.73-8.70 (1H, m) , 8.28-8.25 (1H, m) , 7.73 (1H, d) , 7.58 (1H, dd) , 7.33 (1H, d) , 2.80-2.73 (4H, m) , 2.06-1.97 (1H, m) , 1.96-1.88 (1H, m) . Production Example 67
A mixture of 1.0 g of N- [ 2 -oxo- 6- (pyridin-3-yl ) -2H- pyran-3-yl ] -acetamide and 20 ml of DMF was cooled down to 0°C, and 0.2 g of 55% sodium hydride (oily) was added and the mixture was stirred for 1 hour. Thereafter, 0.56 g of cyclopropanecarbonyl chloride was added, and the mixture was stirred for 20 hours at room
temperature. The reaction mixture was extracted three times with ethyl acetate, and the combined organic layers were washed with saturated saline, and dried over magnesium sulfate. After performing filtration, the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel chromatography to obtain 0.87 g of N-acetyl-N- [ 2 -oxo- 6- (pyridin-3-yl ) -2H- pyran-3-yl] -cyclopropanecarboxamide (hereinafter, referred to as the inventive compound 67) .
Figure imgf000222_0001
Inventive compound 67
1 H-NMR (CDC13) δ : 9.08-9.06 (1H, m) , 8.74-8.71 (1H, m) , 8.16 (1H, dt), 7.47-7.43 (2H, m) , 6.82 (1H, d) , 2.53(3H, s), 1.94-1.87 (1H, m) , 1.21-1.17 (2H, m) , 0.99-0.93 (2H, m) .
Production Example 68
N-acetyl-N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] - acetamide (hereinafter, referred to as the inventive compound 68) was obtained according to the method described in Production Example 67 using acetic
anhydride instead of cyclopropanecarbonyl chloride.
Figure imgf000222_0002
Inventive compound 68
1 H-NMR (CDCI3) δ : 9.08-9.06 (1H, m) , 8.75-8.72 (1H, m) , 8.18-8.15 (1H, m) , 7.46 (1H, dd) , 7.42 (1H, d) , 6.83 (1H, d) , 2.42 (6H, s) .
Production Example 69
N- [2-ΟΧΟ-6- (pyridin-3-yl ) -2H-pyran-3-yl ] -N- propionylacetamide (hereinafter, referred to as the inventive compound 69) was obtained according to the method described in Production Example 67 using
propionic acid chloride instead of cyclopropanecarbonyl chloride .
Figure imgf000223_0001
Inventive compound 69
1 H-NMR (CDC13) δ: 9.08-9.06 (1H, m) , 8.74-8.71 (1H, m) , 8.18-8.14 (1H, m) , 7.45 (1H, ddd) , 7.41 (1H, d) , 6.82 (1H, d) , 2.66 (2H, q) , 2.47 (3H, s), 1.16 (3H, t).
Production Example 70
N-butyryl-N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran- 3-yl ] - acetamide (hereinafter, referred to as the inventive compound 70) was obtained according to the method described in Production Example 67 using butyryl
chloride instead of cyclopropanecarbonyl chloride.
Figure imgf000223_0002
Inventive compound 70
1 H-NMR (CDCI3) δ: 9.08-9.06 (1H, m) > 8.74-8.71 (1H, m) , 8.18-8.14 (1H, m) , 7.47-7.43 (1H, m) , 7.40 (1H, d) , 6.83 (1H, d) , 2.63-2.58 (2H, m) , 2.46 (3H, s), 1.73-1.66 (2H, m) , 0.98-0.93 ( 3H, m) .
Production Example N-isobutyryl-N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran-3- yl ] -acetamide (hereinafter, referred to as the inventive compound 71) was obtained according to the method described in Production Example 67 using isobutyryl chloride instead of cyclopropanecarbonyl chloride.
Figure imgf000224_0001
Inventive compound 71
1 H-N R (CDC13) δ: 9.08-9.06 (1H, m) , 8.74-8.71 (1H, m) , 8.16 (1H, ddd) , 7.47-7.43 (1H, m) , 7.39 (1H, d) , 6.82 (1H, d) , 3.08-3.01 (1H, m) , 2.46 (3H, s), 1.20 (6H, d) .
Production Example 72
N- [2-OXO-6- (pyridin-3-yl ) -2H-pyran-3-yl ] -N- pentanoyl-acetamide (hereinafter, referred to as the inventive compound 72) was obtained according to the method described in Production Example 67 using
pentanoyl chloride instead of cyclopropanecarbonyl chloride .
Figure imgf000224_0002
Inventive compound 72
1 H-NMR (CDCI3) δ: 9.08-9.06 (1H, m) , 8.74-8.72 (1H, m) , 8.16 (1H, ddd), 7.48-7.43 (1H, m) , 7.39 (1H, d) , 6.82 (1H, d) , 2.62 (2H, t), 2.46 (3H, s), 1.69-1.61 (2H, m) , 1.39-1.31 (2H, m) , 0.91 (3H, t).
Production Example 73
N- (2-butenoyl) -N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran-3- yl ] -acetamide (hereinafter, referred to as the inventive compound 73) was obtained according to the method described in Production Example 67 using 2-butenoyl chloride instead of cyclopropanecarbonyl chloride.
Figure imgf000225_0001
Inventive compound 73
1 H-NMR (CDC13) δ: 9.09-9.07 (1H, m) , 8.74-8.71 (1H, m) , 8.19-8.15 (1H, m) , 7.47-7.43 (1H, m) , 7.37 (1H, d) , 7.19-7.10 (1H, m) , 6.82 (1H, d) , 6.18 (1H, dd) , 2.52 (3H, s) , 1.92-1.88 (3H, m) .
Production Example 74
N-pivaloyl-N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] - acetamide (hereinafter, referred to as the inventive compound 74) was obtained according to the method described in Production Example 67 using pivaloyl chloride instead of cyclopropanecarbonyl chloride.
Figure imgf000226_0001
Inventive compound 74
1 H-NMR (CDC13) δ: 9.08-9.05 (1H, m) , 8.73-8.70 (1H, m) , 8.16 (1H, dt), 7.47-7.43 (1H, m) , 7.32. (1H, d) , 6.79 (1H, d) , 2.31 (3H, s), 1.31 (9H, s).
Production Example 75
N-acetyl-N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] - carbamic acid methyl ester (hereinafter, referred to as the inventive compound 75) was obtained according to the method described in Production Example 67 using methyl chlorocarbonate instead of cyclopropanecarbonyl
chloride .
Figure imgf000226_0002
Inventive compound
1 H-NMR (CDCI3) δ: 9.06-9.04 (1H, m) , 8.72-8.69 (1H, m) , 8.17-8.13 (1H, m) , 7.43 (1H, dd) , 7.33 (1H, d) , 6.78 (1H, d) , 3.81 (3H, s), 2.68 (3H, s).
Production Example 76
N-acetyl-N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] - carbamic acid chloromethyl ester (hereinafter, referred to as the inventive compound 76) was obtained according to the method described in Production Example 67 using chloromethyl chlorocarbonate instead of
c clopropanecarbonyl chloride.
Figure imgf000227_0001
Inventive compound 76
1 H-NMR (CDC13) δ: 9.07-9.06 (1H, m) , 8.73-8.71 (1H, m) , 8.17-8.14 (1H, m) , 7.44 (1H, dd) , 7.37 (1H, d) , 6.81 (1H, d) , 5.76 (2H, s), 2.72 (3H, s).
Production Example 77
N-acetyl-N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] - methanesulfoneamide (hereinafter, referred to as the inventive compound 77) was obtained according to the method described in Production Example 67 using
methanesulfonyl chloride instead of cyclopropanecarbonyl chloride .
Figure imgf000227_0002
Inventive compound 77
1 H-NMR (CDCI3 ) δ: 9.10-9.08 (1H, m) , 8.77-8.74 (1H, m) , 8.16 (1H, dd) , 7.70 (1H, d) , 7.47 (1H, dd) , 6.88 (1H, d) , 3.53 (3H, s) , 2.22 (3H, s) . Production Example 78
N-benzyl-N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] - acetamide (hereinafter, referred to as the inventive compound 78) was obtained according to the method described in Production Example 67 using benzyl bromide ropanecarbonyl chloride.
Figure imgf000228_0001
Inventive compound 78
1 H-NMR (CDC13) δ : 9.01-9.00 (1H, m) , 8.71-8.69 (1H, m) , 8.12-8.10 (1H, m) , 7.42 (1H, dd) , 7.31-7.26 (6H, m) , 6.61 (1H, d) , 2.96 (1H, s), 2.88 (1H, s), 2.09 (3H, br s) .
Production Example 79
N-acetyl-N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] - benzamide (hereinafter, referred to as the inventive compound 79) (0.25 g) was obtained according to the method described in Production Example 67 using benzoyl chloride instead of cyclopropanecarbonyl chloride.
Figure imgf000228_0002
Inventive compound 79 1 H-NMR (CDC13) δ: 8.99-8.96 (1H, m) , 8.69-8.67 (1H, m) ,
8.10-8.06 (1H, m) , 7.73-7.69 (2H, m) , 7.52-7.47 (1H, m) ,
7.43-7.37 (3H, m) , 7.23 (1H, d) , 6.64 (1H, d) , 2.55 (3H, s) .
Production Example 80
N-acetyl-N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] -2 chlorobenzamide (hereinafter, referred to as the
inventive compound 80) was obtained according to the method described in Production Example 67 using 2- chloro-benzoyl chloride instead of cyclopropanecarbonyl chloride .
Figure imgf000229_0001
Present active compound 80
1 H-NMR (CDCI3) δ: 8.97-8.94 (1H, m) , 8.68-8.66 (1H, m) ,
8.07-8.01 (1H, m) , 7.55-7.51 (2H, m) , 7.41-7.37 (1H, m) ,
7.34-7.30 (2H, m) , 7.30-7.27 (1H, m) , 6.66 (1H, d) , 2.68 (3H, s) . Production Example 81
N-acetyl-N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] -3- chlorobenzamide (hereinafter, referred to as the
inventive compound 81) was obtained according to the method described in Production Example 67 using 3- chloro-benzoyl chloride instead of cyclopropanecarbonyl chloride .
Figure imgf000230_0001
Inventive compound 81
1 H-NMR (CDC13) δ: 9.01-8.99 (1H, m) , 8.71-8.68 (1H, m) , 8.12-8.08 (1H, m) , 7.71-7.69 (1H, m) , 7.59-7.55 (1H, m) 7.48-7.45 (1H, m) , 7.44-7.39 (1H, m) , 7.36-7.31 (1H, m) 7.30-7.28 (1H, m) , 6.69 (1H, d) , 2.55-2.53 (3H, m) .
Production Example 82
N-acetyl-N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] -4 chlorobenzamide (hereinafter, referred to as the
inventive compound 82) was obtained according to the method described in Production Example 67 using 4- chloro-benzoyl chloride instead of cyclopropanecarbonyl chloride .
Figure imgf000230_0002
Inventive compound
1 H-NMR (CDCI3) δ: 9.01-8.99 (1H, m) , 8.71-8.69 (1H, m) , 8.12-8.08 (1H, m) , 7.68-7.64 (2H, m) , 7.44-7.40 (1H, m) , 7.40-7.36 (2H, m) , 7.28-7.26 (1H, m) , 6.69 (1H, t), 2.54 (3H, d) .
Production Example 83
A mixture of 0.9 g of [ 2-oxo- 6- (pyridin-3-yl ) -2H- pyran-3-yl ] -cyclopropanecarboxamide and 30 ml of DMF was cooled down to 0°C, and 0.17 g of 55% sodium hydride (oily) was added and the mixture was stirred for 1 hour. Thereafter, 0.6 g of methyl iodide was added, and the mixture was stirred for 20 hours at room temperature. The reaction mixture was extracted three times with ethyl acetate, and the combined organic layers were washed with saturated saline, and dried over magnesium sulfate. After performing filtration, the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel chromatography to obtain 0.45 g of N-methyl-N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] - cyclopropanecarboxamide (hereinafter, referred to as the inventive compound 83) .
Figure imgf000231_0001
Inventive compound 83
1 H-NMR (CDC13) δ: 9.07-9.05 (1H, m) , 8.72-8.69 (1H, m) 8.15 (1H, dt), 7.48 (1H, d) , 7.44 (1H, dd) , 6.78 (1H, d) , 3.26 (3H, s), 1.61-1.56 (1H, m) , 1.12-1.05 (2H, m) 0.80-0.75 (2H, m) . Production Example 84
N-ethyl-N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] - cyclopropanecarboxamide (hereinafter, referred to as the inventive compound 84) was obtained according to the method described in Production Example 83 using ethyl iodide instead of methyl iodide.
Figure imgf000232_0001
Inventive compound 84
1 H-NMR (CDC13) δ: 9.08-9.06 (1H, m) , 8.73-8.70 (1H, m) , 8.16 (1H, dt), 7.47-7.42 (2H, m) , 6.79 (1H, d) , 1.70-
1.66 (2H, m) , 1.51 (1H, s), 1.17 (3H, t), 1.12-1.03 (2H, m) , 0.79-0.73 (2H, m) .
Production Example 85
N-cyclopropanecarbonyl-N- [2-oxo-6- (pyridin-3-yl ) -2H- pyran-3-yl] -cyclopropanecarboxamide (hereinafter, referred to as the inventive compound 85) was obtained according to the method described in Production Example 83 using cyclopropanecarboxylic acid chloride instead of methyl iodide.
Figure imgf000232_0002
Inventive compound 1 H-NMR (CDC13) δ : 9.07-9.05 (1H, m) , 8.73-8.70 (1H, m) , 8.17-8.13 (1H, m) , 7.46-7.43 (2H, m) , 6.83-6.80 (1H, m) , 2.25-2.19 (2H, m) , 1.23-1.19 (4H, m) , 1.02-0.97 (4H, m) . Production Example 86
N-cyclopropanecarbonyl-N- [2-oxo-6- (pyridin-3-yl ) -2H- pyran-3-yl ] -carbamic acid methyl ester (hereinafter, referred to as the inventive compound 86) was obtained according to the method described in Production Example 83 using methyl chlorocarbonate instead of methyl iodide .
Figure imgf000233_0001
Inventive compound 86
1 H-NMR (CDCI3) δ : 9.05-9.03 (1H, m) , 8.71-8.69 (1H, m) , 8.14-8.12 (1H, m) , 7.42 (1H, dd) , 7.32 (1H, d) , 6.76
(1H, d) , 3.83 (3H, s), 3.04-2.97 (1H, m) , 1.22-1.18 (2H, m) , 1.08-1.03 (2H, m) .
Production Example 87
N-cyclopropanecarbonyl-N- [2-oxo-6- (pyridin-3-yl ) -2H- pyran-3-yl ] -carbamic acid ethyl ester (hereinafter, referred to as the inventive compound 87) was obtained according to the method described in Production Example 83 using ethyl chlorocarbonate instead of methyl iodide.
Figure imgf000234_0001
Inventive compound 87
1 H-NMR (CDC13) δ : 9.06-9.04 (1H, m) , 8.71-8.68 (1H, m) , 8.15-8.13 (1H, m) , 7.44-7.41 (1H, m) , 7.32 (1H, d) , 6.76 (1H, d) , 4.29 (2H, q) , 3.02-2.96 (1H, m) , 1.29 (3H, t), 1.21-1.17 (2H, m) , 1.07-1.02 (2H, m) .
Production Example 88
N-methoxymethyl-N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran- 3-yl ] -cyclopropanecarboxamide (hereinafter, referred to as the inventive compound 88) was obtained according to the method described in Production Example 83 using chloromethyl methyl ether instead of methyl iodide.
Figure imgf000234_0002
Inventive compound 88
MS+ 301
Production Example 89
N-ethoxymethyl-N-2-oxo-6- (pyridin-3-yl ) -2H-pyran-3- yl ] -cyclopropanecarboxamide (hereinafter, referred to as the inventive compound 89) was obtained according to the method described in Production Example 83 using
chloromethyl ethyl ether instead of methyl iodide.
Figure imgf000235_0001
Inventive compound 89
S+ 315
Production Example 90
N-benzyloxymethyl-N- [2-oxo-6- (pyridin-3-yl ) -2H- pyran-3-yl] -cyclopropanecarboxamide (hereinafter, referred to as the inventive compound 90) was obtained according to the method described in Production Example 83 using chloromethyl benzyl ether instead of methyl iodide .
Figure imgf000235_0002
Inventive compound 90
MS+ 377
Production Example 91
N-methyl-N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] - acetamide (hereinafter, referred to as the inventive compound 91) was obtained according to the method described in Production Example 83 using N-[2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] -acetamide instead of N-[2- oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] - c clopropanecarboxamide .
Figure imgf000236_0001
Inventive compound 91
1 H-NMR (CDC13) δ: 9.07-9.05 (1H, m) , 8.73-8.70 (1H, m) , 8.17-8.13 (1H, m) , 7.46-7.42 (2H, m) , 6.78 (1H, d) , 3.23 (3H, s) , 2.08 (3H, br s) .
1 H-NMR (DMS0-D6) δ: 9.12-9.09 (1H, m) , 8.71-8.68 (1H, m) , 8.28-8.24 (1H, m) , 7.86-7.81 (1H, m) , 7.60-7.55 (1H, m) , 7.29 (1H, d) , 3.06 (3H, s), 1.94 (3H, s).
Production Example 92
N-methyl-N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] - cyclobutanecarboxamide (hereinafter, referred to as the inventive compound 92) was obtained according to the method described in Production Example 83 using N-[2- oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl] - cyclobutanecarboxamide instead of N- [ 2-oxo-6- (pyridin-3- yl) -2H-pyran-3-yl] -cyclopropanecarboxamide .
Figure imgf000236_0002
Inventive compound 92
1 H-NMR (CDC13) δ: 9.07-9.05 (1H, m) , 8.72-8.70 (1H, m) , 8.17-8.13 (1H, m) , 7.44 (1H, dd) , 7.33 (1H, d) , 6.76 (1H, d) , 3.19 (4H, s), 2.42-2.33 (2H, m) , 2.04-1.94 (2H, m) , 1.91-1.81 (2H, m) .
Production Example 93
N-methyl-N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] - cyclopentanecarboxamide (hereinafter, referred to as the inventive compound 93) was obtained according to the method described in Production Example 83 using N-[2- oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] - cyclopentanecarboxamide instead of N- [2-oxo-6- (pyridin- 3-yl) -2H-pyran-3-yl ] -cyclopropanecarboxamide.
Figure imgf000237_0001
Inventive compound 93
1 H-NMR (CDCI3) δ: 9.07-9.05 (1H, m) , 8.72-8.70 (1H, m) , 8.15 (1H, dt), 7.44 (1H, dd) , 7.40 (1H, d) , 6.78 (1H, d) , 3.22 (3H, s), 2.77-2.67 (1H, m) , 1.89-1.81 (2H, m) , 1.79-1.72 (2H, m) , 1.71-1.69 (2H, m) , 1.54-1.48 (2H, m)
Production Example 94
N-methyl-N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] - cyclohexanecarboxamide (hereinafter, referred to as the inventive compound 94) was obtained according to the method described in Production Example 83 using N-[2- oxo-6- (pyridin-3-yl) -2H-pyran-3-yl ] - cyclohexanecarboxamide instead of N- [ 2-oxo-6- (pyridin-3- yl) -2H-pyran-3-yl ] -cyclopropanecarboxamide.
Figure imgf000238_0001
Inventive compound 94
1 H-NMR (CDC13 ) δ: 9.09-9.06 (1H, m) , 8.73-8.70 (1H, m) , 8.17 (1H, t), 7.45 (1H, dd) , 7.40 (1H, d) , 6.81-6.77 (1H, m) , 3.20 (3H, s), 2.36-2.25 (1H, m) , 1.80-1.71 (4H, m) , 1.66-1.60 (1H, m) , 1.59-1.50 (2H, m) , 1.28-1.12 (3H, m) .
Production Example 95
N-methyl-N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] - 2 , 2 , 2-trifluoro-acetamide (hereinafter, referred to as the inventive compound 95) was obtained according to the method described in Production Example 83 using N-[2- oxo-6- (pyridin-3-yl) -2H-pyran- 3-yl ] -2,2,2-trifluoro- acetamide instead of N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran- 3-yl] -cyclopropanecarboxamide.
Figure imgf000238_0002
Inventive compound 95
1 H-NMR (CDC13) δ : 9.08-9.06 (1H, m) , 8.75-8.73 (1H, m) ,
8.17-8.15 (1H, m) , 7.49 (1H, d) , 7.48-7.44 (1H, m) , 6.79 (1H, d) , 3.34 (3H, s) .
Production Example 96
N-methyl-N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] - 2,2,3,3, 3-pentafluoro-propionamide (hereinafter,
referred to as the inventive compound 96) was obtained according to the method described in Production Example 83 using N- [ 2-oxo- 6- (pyridin-3-yl ) -2H-pyran-3-yl ] - 2 , 2 , 3 , 3 , 3-pentafluoro-propionamide instead of N- [2-oxo- 6- (pyridin-3-yl ) -2H-pyran-3-yl ] -cyclopropanecarboxamide .
Figure imgf000239_0001
Inventive compound 96
1 H-NMR (CDCI3) δ : 9.07-9.07 (1H, m) , 8.74-8.73 (1H, m) , 8.17-8.14 (1H, m) , 7.50-7.44 (2H, m) , 6.78 (1H, d) , 3.34 (3H, s) .
Production Example 97
N-acetyl-N- [6- ( 5-bromopyridin- 3-yl ) -2 -oxo-2H-pyran- 3-yl ] -cyclopropanecarboxamide (hereinafter, referred to as the inventive compound 97) was obtained according to the method described in Production Example 83 using N- [6- ( 5-bromopyridin-3-yl ) -2-oxo-2H-pyran-3-yl ] -acetamide instead of N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] - cyclopropanecarboxamide, and using cyclopropanecarbonyl chloride instead of methyl iodide.
Figure imgf000240_0001
Inventive compound 97
1 H-NMR (CDC13) δ: 8.97-8.95 (1H, m) , 8.78-8.77 (1H, m) , 8.32-8.30 (1H, m) , 7.45 (1H, d) , 6.83 (1H, d) , 2.53 (3H, s), 1.90-1.84 (1H, m) , 1.21-1.17 (2H, m) , 0.99-0.94 (2H, m) .
Production Example 98
N-methyl-N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] -4- nitro-benzamide (hereinafter, referred to as the
inventive compound 98) was obtained according to the method described in Production Example 83 using N-[2- oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] -4 -nitro-benzamide instead of N- [2-oxo-6- (pyridin-3-yl) -2H-pyran-3-yl] - cyclopropanecarboxamide .
Figure imgf000240_0002
Present active compound
-N R (CDCI3) δ: 8.99-8.97 (1H, m) , 8.70-8.67 (1H, 8.20-8.16 (2H, m) , 8.09-8.05 (1H, m) , 7.66-7.62 (2H, m) , 7.44-7.39 (1H, m) , 7.21 (1H, d) , 6.63 (1H, d) , 3.40 (3H, s) . Production Example 99
N-methyl-N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] - benzamide (hereinafter, referred to as the inventive compound 99) was obtained according to the method described in Production Example 83 using N- [ 2 -oxo- 6- (pyridin-3-yl ) -2H-pyran-3-yl ] -benzamide instead of N-[2- oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] - c clopropanecarboxamide .
Figure imgf000241_0001
Present active compound 99
1 H-NMR (CDC13) δ : 8.97-8.96 (1H, m) , 8.68-8.66 (1H, m) , 8.09-8.06 (1H, m) , 7.47-7.44 (2H, m) , 7.42-7.38 (1H, m) , 7.36-7.33 (1H, m) , 7.33-7.30 (2H, m) , 7.06 (1H, d) , 6.55 (1H, d) , 3.38 (3H, s) .
Production Example 100
N-methanesulfonyl-N- [2-oxo-6- (pyridin-3-yl ) -2H- pyran-3-yl ] -methanesulfonic acid amide (hereinafter, referred to as the inventive compound 100) was obtained according to the method described in Production Example 31 using methanesul fonyl chloride instead of acryloyl chloride .
Figure imgf000242_0001
Inventive compound 100
1 H-NMR (DMSO-D6) δ: 9.16-9.14 (1H, m) , 8.75-8.73 (1H, m) , 8.33-8.30 (1H, m) , 8.23 (1H, d) , 7.62-7.58 (1H, m) , 7.41 (1H, d) , 3.59 (6H, s) .
Production Example 101
N- ( 3-chloropropanesulfonyl ) -N- [2-oxo-6- (pyridin-3- yl) -2H-pyran-3-yl] -3-chloropropanesulfonic acid amide (hereinafter, referred to as the inventive compound 101) was obtained according to the method described in
Production Example 31 using 3-chloropropanesulfonyl chloride instead of acryloyl chloride.
Figure imgf000242_0002
Inventive compound 101
1 H-NMR (CDC13) δ: 9.08-9.06 (1H, m) , 8.76-8.74 (1H, m) , 8.18-8.15 (1H, m) , 7.65 (1H, d) , 7.48-7.44 (1H, m) , 6.84 (1H, d) , 3.89-3.84 (4H, m) , 3.72-3.68 (4H, m) , 2.46-2.42 (4H, m) . Production Example 102
To a mixture of 1.5 g of 3-amino-6- (pyridin-3-yl ) - pyran-2-one and 50 ml of chloroform was added 0.4 ml of bromine and the mixture was stirred at room temperature for 10 hours, then, the precipitate was filtrated. The resultant precipitate was added to a mixture of 50 ml of water, 1.1 g of sodium carbonate and 0.25 g of sodium hydrogen sulfite, and the mixture was stirred at room temperature for 3 hours. The precipitate was filtrated, and the filtrated precipitate was washed with 10 ml of water and 10 ml of hexane, and dried under reduced pressure to obtain 1.4 g of 3-amino-4-bromo-6- (pyridin- 3-yl ) -pyran-2-one (hereinafter, referred to as the inventive compound 102) .
Figure imgf000243_0001
Inventive compound 102
1 H-NMR (DMSO-D6) δ: 8.97-8.95 (1H, m) , 8.54 (1H, d) , 8.12-8.08 (1H, m) , 7.46 (1H, dd) , 7.41 (1H, s), 6.00 (2H, s) .
Production Example 103
To 5 ml of chloroform was added 0.5 g of 3-amino-6- (pyridin-3-yl) -pyran-2-one and 0.36 g of N- chlorosuccinimide, and the mixture was stirred for 30 minutes under reflux with heat. After standing to cool, the mixture was poured into water, and the resultant mixture was extracted three times with chloroform, and the organic layers were combined and dried over
anhydrous magnesium sulfate, then, concentrated. The residue was subjected to silica gel column
chromatography to obtain 0.14 g of 3-amino-4-chloro-6- (pyridin-3-yl ) -pyran-2-one (hereinafter, referred to as the inventive compound 103) .
Figure imgf000244_0001
Inventive compound 103
1 H-NMR (DMSO-D6) δ: 8.96 (d, 1H) , 8.54 (dd, 1H) , 8.12- 8.08 (m, 1H) , 7.47 (dd, 1H) , 7.35 (s, 1H) , 6.05 (s, 2H)
Production Example 104
To a mixture of 2.0 g of 3-amino-4-bromo-6- (pyridin- 3-yl ) -pyran-2-one and 30 ml of pyridine was added 1.7 g of cyclopropanecarbonyl chloride, and the mixture was stirred at room temperature for 20 hours. Water (10 ml) was added, and the reaction mixture was extracted three times with ethyl acetate, and the combined organic layers were washed with saturated saline, and dried over magnesium sulfate. After performing filtration, the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel chromatography to obtain 2.1 g of N- [ 4-bromo2-oxo-6- (pyridin-3-yl ) -2H- pyran-3-yl] -N-cyclopropanecarbonyl- cyclopropanecarboxamide (hereinafter, referred to as the inventive compound 104) .
Figure imgf000245_0001
Inventive compound 104
1 H-NMR (CDC13) δ: 9.06-9.04 (1H, m) , 8.76-8.74 (1H, m) , 8.15-8.13 (1H, m) , 7.45 (1H, dd) , 7.01 (1H, s), 2.27- 2.20 (2H, m) , 1.25-1.21 (4H, m) , 1.02-0.97 (4H, m) .
1 H-NMR (DMSO-D6) δ: 9.15 (1H, s), 8.75-8.72 (1H, m) , 8.32 (1H, d) , 7.80 (1H, s), 7.61-7.56 (1H, m) , 2.35-2.34 (2H, m) , 0.99-0.95 (8H, m) .
Production Example 105
N- [ 4 -chloro-2 -oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] -N- cyclopropanecarbonyl-cyclopropanecarboxamide
(hereinafter, referred to as the inventive compound 105) was obtained according to the method described in
Production Example 104 using 3-amino-4-chloro-6- (pyridin-3-yl ) -pyran-2-one instead of 3-amino-4 -bromo- 6- (pyridin-3-yl ) -pyran-2 -one .
Figure imgf000245_0002
Inventive compound 105
1 H-NMR (DMSO-D6) δ: 9.06 (dd, 1H) , 8.75 (dd, 1H) , 8.16- 8.12 (m, 1H) , 7.46 (ddd, 1H) , 6.89 (s, 1H) , 2.27-2.20 (m, 2H) , 1.25-1.19 (m, 4H) , 1.02-0.97 (m, 4H)
Production Example 106
To 1 ml of DMF was added 0.15 g of N- [ 4 -amino-2-oxo- 6- (pyridin-3-yl ) -2H-pyran-3-yl ] -N-cyclopropanecarbonyl- cyclopropanecarboxamide and 0.08 g of dimethylamine (50% aqueous solution) , and the mixture was stirred at room temperature for 18 hours. The mixture was poured into water, and the precipitate was filtrated. The resultant filtrated product was washed with water and t-butyl methyl ether, then, dried under reduced pressure to obtain 0.08 g of N- [ 4 -amino-2 -oxo- 6- (pyridin-3-yl ) -2H- pyran-3-yl] -cyclopropanecarboxamide (hereinafter, referred to as the inventive compound 106) .
Figure imgf000246_0001
Inventive compound 106
1 H-NMR (DMSO-D6) δ: 8.96 (s, 1H) , 8.92 (s, 1H) , 8.67 (d, 1H) , 8.09 (d, 1H) , 7.55 (dd, 1H) , 6.70 (s, 2H) , 1.84- 1.77 (m, 1H) , 0.77-0.70 (m, 4H)
Production Example 107
To a mixed solvent of 1 ml of toluene and 1 ml of ethanol was added 0.44 g of N- [ 4 -bromo-2 -oxo- 6- (pyridin- 3-yl) -2H-pyran-3-yl] -N-cyclopropanecarbonyl- cyclopropanecarboxamide , 0.11 g of triethylamine and 0.09 g of methylamine (40% aqueous solution), and the resultant mixture was stirred with heating at 80°C for 20 hours. After standing to cool, the mixture was concentrated, then, water was added, and the mixture was extracted three times with ethyl acetate. The organic layers were combined and dried over anhydrous magnesium sulfate, then, concentrated. The residue was subjected to silica gel column chromatography to obtain 0.16 g of N- [4-methylamino-2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] - cyclopropanecarboxamide (hereinafter, referred to as the inventive compound 107) .
Figure imgf000247_0001
Inventive compound 107
1 H-NMR (DMSO-D6) δ: 9.12 (s, 1H) , 8.87 (s, 1H), 8.68 (d, 1H), 8.27 (d, 1H) , 7.56 (dd, 1H) , 6.99 (s, 1H), 6.74- 6.68 (m, 1H) , 2.93 (d, 3H) , 1.82-1.75 (m, 1H) , 0.77-0.71 (m, 4H)
Production Example 108
N- [ 4-cyclopropylamino-2-oxo-6- (pyridin-3-yl ) -2H- pyran-3-yl] -cyclopropanecarboxamide (hereinafter, referred to as the inventive compound 108) was obtained according to the method described in Production Example 107 using cyclopropylamine instead of methylamine.
Figure imgf000248_0001
Inventive compound 108
1 H-N R (DMSO-D6) δ: 9.08 (d, 1H) , 8.87 (s, 1H) , 8.69 (dd, 1H) , 8.23 (d, 1H) , 7.57 (dd, 1H) , 7.15 (s, 1H) , 6.96 (s, 1H) , 2.75-2.69 (m, 1H) , 1.82-1.75 (m, 1H) , 0.87-0.81 (m, 2H) , 0.75-0.71 (m, 4H) , 0.61-0.56 (m, 2H)
Production Example 109
To a mixture of 0.3 g of N- [ 4 -bromo-2 -oxo- 6- (pyridin-3-yl ) -2H-pyran-3-yl ) -N-cyclopropanecarbonyl- cyclopropanecarboxamide and 10 ml of THF was added 0.18 g of pyrrolidine, and the mixture was stirred at room temperature for 5 hours. Water (10 ml) was added, and the reaction mixture was extracted three times with ethyl acetate, and the combined organic layers were washed with saturated saline, and dried over magnesium sulfate. After performing filtration, the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel chromatography to obtain 0.2 g of N- [2 -oxo- 6- (pyridin-3-yl) -4- (pyrrolidin-l-yl) -2H- pyran-3-yl] -cyclopropanecarboxamide (hereinafter, referred to as the inventive compound 109) .
Figure imgf000249_0001
Inventive compound 109
1 H-NMR (CDC13) δ: 8.98-8.96 (1H, m) , 8.67-8.65 (1H, m) , 8.10-8.08 (1H, m) , 7.64 (1H, s), 7.38 (1H, dd) , 6.50 (1H, s), 3.76-3.68 (2H, m) , 3.56-3.49 (2H, m) , 2.07-1.99 (2H, m) , 1.96-1.88 (2H, m) , 1.79-1.73 (1H, m) , 1.09-0.98 (2H, m) , 0.86-0.81 (2H, m) .
Production Example 110
To a mixed solution of 6 ml of DMF, 6 ml of THF and
6 ml of water was added coarse N- [ 4-azide-2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] -N-cyclopropanecarbonyl- cyclopropanecarboxamide and 1.17 g of triphenylphosphine and the mixture was stirred at room temperature for 6 hours. The mixture was poured into IN hydrochloric acid and the resultant mixture was extracted twice with t- butyl methyl ether. The aqueous layer was rendered basic by addition of sodium carbonate, then, the layer was extracted three times with ethyl acetate. The resultant organic layers were combined and dried over anhydrous magnesium sulfate, then, concentrated. The residue was subjected to silica gel column
chromatography to obtain 0.91 g of N- [ 4 -amino-2-oxo- 6- (pyridin-3-yl ) -2H-pyran-3-yl ] -N-cyclopropanecarbonyl- cyclopropanecarboxamide (hereinafter, referred to as the inventive compound 110) .
Figure imgf000250_0001
Inventive compound 110
1 H-NMR (D SO-D6) δ: 8.95 (d, 1H) , 8.70 (dd, 1H) , 8.11-
8.15 (m, 1H) , 7.57 (dd, 1H) , 7.34 (s, 2H) , 6.74 (s, 1H),
2.37-2.30 (m, 2H) , 0.90-0.83 (m, 8H)
Production Example 111
To 2 ml of DMF was added 0.3 g of N- [ 4 -amino-2 -oxo- 6- (pyridin-3-yl ) -2H-pyran-3-yl ] -N-cyclopropanecarbonyl- cyclopropanecarboxamide and 0.27 g of triethylamine .
Then, 0.1 g of acetyl chloride was added at room
temperature, and the mixture was stirred with heating at 80°C for 12 hours. After standing to cool, the mixture was poured into water, and the resultant mixture was extracted three times with ethyl acetate, and the organic layers were combined and dried over anhydrous magnesium sulfate, then, concentrated. The residue was subjected to silica gel column chromatography to obtain 0.09 g of N, N' - [2-OXO-6- (pyridin-3-yl) -2H-pyran-3, 4- diyl ] -biscyclopropanecarboxamide (hereinafter, referred to as the inventive compound 111) .
Figure imgf000251_0001
Inventive compound 111
1 H-NMR (DMSO-D6) δ: 9.92 (s, 1H) , 9.58 (s, 1H), 8.94 (d, 1H) , 8.68 (d, 1H) , 8.16-8.13 (m, 1H) , 7.88 (s, 1H) , 7.55 (dd, 1H) , 2.09-2.02 (m, 1H) , 1.98-1.92 (m, 1H), 0.92- 0.87 (m, 4H) , 0.85-0.80 (m, 4H)
Production Example 112
To a mixture of 0.4 g of N- [ 4-bromo2-oxo-6- (pyridin- 3-yl) -2H-pyran-3-yl ) -N-cyclopropanecarbonyl- cyclopropanecarboxamide and 10 ml of ethanol was added 0.17 g of sodium methyl mercaptan, and the mixture was stirred at room temperature for 8 hours. Water (10 ml) was added, and the reaction mixture was extracted three times with ethyl acetate, and the combined organic layers were washed with saturated saline, and dried over magnesium sulfate. After performing filtration, the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel chromatography to obtain 0.3 g of N- [ 4 -methylthio2-oxo- 6- (pyridin-3-yl ) - 2H-pyran-3-yl ] -cyclopropanecarboxamide (hereinafter, referred to as the inventive compound 112) .
Figure imgf000252_0001
Inventive compound 112
1 H-NMR (D SO-D6) δ: 9.63 (1H, s), 9.15 (1H, d), 8.70-
8.68 (1H, m) , 8.29 (1H, d) , 7.56 (1H, dd) , 7.18 (1H,
2.59 (3H, s), 1.84-1.78 (1H, m) , 0.79-0.72 (4H, m) .
Production Example 113
To a mixture of 20 ml of THF and 0.63 g of 2,2,2- trifluoroethanethiol was added 0.22 g of 55% sodium hydride (oily) at 0°C, and the mixture was stirred for 0.5 hours. Thereafter, 0.87 g of N- [ 4 -bromo-2-oxo- 6- (pyridin-3-yl ) -2H-pyran-3-yl ) -N-cyclopropanecarbony- lcyclopropanecarboxamide was added, and the mixture was stirred at room temperature for 7 hours. Water (10 ml) was added, and the reaction mixture was extracted three times with ethyl acetate, and the combined organic layers were washed with saturated saline, and dried over magnesium sulfate. After performing filtration, the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel chromatography to obtain 0.3 g of N- [ 2 -oxo- 6- (pyridin-3-yl ) -4 - ( 2 , 2 , 2- trifluoroethylthio ) -2H-pyran-3-yl ] - cyclopropanecarboxamide (hereinafter, referred to as the inventive compound 113) .
Figure imgf000253_0001
Inventive compound 113
1 H-N R (DMSO-D6) δ: 9.92 (1H, s), 9.16-9.14 (1H, m) , 8.70 (1H, d) , 8.28 (1H, d) , 7.58 (1H, dd) , 7.42 (1H, s), 4.34 (2H, q) , 1.90-1.84 (1H, m) , 0.84-0.79 (2H, m) , 0.78-0.75 (2H, m) .
Production Example 114
To a mixture of 2.9 g of a boron trifluoride (63%)- methanol solution and 30 ml of methanol was added, at room temperature, 1.5 g of N-benzyl-N- [2-oxo-6- (pyridin- 3-yl ) -2H-pyran-3-yl ] -acetamide , and the mixture was stirred for 8 hours under reflux with heat. The solvent was distilled off under reduced pressure, and 300 ml of a potassium carbonate aqueous solution (potassium carbonate 1.9 g) was added at room temperature, and the mixture was stirred for 1 hour. The reaction mixture was extracted three times with ethyl acetate, and the organic layers were washed with saturated saline and dried over magnesium sulfate. After performing
filtration, the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel chromatography to obtain 0.52 g of 3-benzylamino-6- (pyridin-3-yl) -pyran-2-one (hereinafter, referred to as the inventive compound 114).
Figure imgf000254_0001
Inventive compound 114
1 H-N R (CDC13) δ: 8.92-8.90 (1H, m) , 8.54-8.51 (1H, m) , 7.99-7.97 (1H, m) , 7.39-7.29 (6H, m) , 6.66 (1H, d) , 6.06 (1H, d) , 5.43-5.37 (1H, m) , 4.36 (2H, d) .
Production Example 115
To a mixture of 0.5 g of N- [2-oxo-6- (pyridin-3-yl) - 2H-pyran-3-yl ] -cyclopropanecarboxamide and 10 ml of chloroform was added, at room temperature, 0.44 g of 77% m-chloroperbenzoic acid. The mixture was stirred at room temperature for 20 hours. A sodium hydrogen sulfite aqueous solution (10 ml) (sodium hydrogen sulfite 0.2 g) was added, and the reaction mixture was extracted three times with chloroform, and the combined organic layers were dried over magnesium sulfate. Filtration was performed, and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel chromatography to obtain 0.09 g of N- [2-oxo-6- ( 1- oxypyridin-3-yl ) -2H-pyran-3-yl ] -cyclopropanecarboxamide (hereinafter, referred to as the inventive compound 115) .
Figure imgf000255_0001
Inventive compound 115
1 H-NMR (DMSO-D6) δ: 10.12 (1H, br s), 8.60 (1H, s), 8.26-8.23 (1H, m) , 8.20 (1H, d) , 7.72-7.67 (1H, m) , 7.53-7.49 (1H, m) , 7.29 (1H, d), 2.30-2.24 (1H, m) , 0.81-0.80 (4H, m) .
Production Example 116
N- [2-OXO-6- ( l-oxypyridin-3-yl ) -2H-pyran-3-yl ] - acetamide (hereinafter, referred to as the inventive compound 116) was obtained according to the method described in Production Example 115 using N-[2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] -acetamide instead of N-[2- oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] - cyclopropanecarboxamide.
Figure imgf000255_0002
Inventive compound 116
1 H-NMR (DMSO-D6) δ: 9.86 (1H, s), 8.62 (1H, s), 8.27- 8.24 (1H, m) , 8.23 (1H, d) , 7.72-7.69 (1H, m) , 7.55-7.50 (1H, m) , 7.30 (1H, d) , 2.15 (3H, s). Production Example 117
To 1.5 ml of DMF was added 0.22 g of N-[2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] -carbamic acid phenyl ester and 0.2 g of pyrrolidine at room temperature, and the mixture was stirred for 4 hours. The mixture was poured into water, and the precipitate was filtrated. The resultant filtrated product was washed with water and t- butyl methyl ether, then, drying under reduced pressure was performed to obtain 0.1 g of N- [2-oxo-6- (pyridin-3- yl ) -2H-pyran-3-yl ] -1-pyrrolidine carboxamide
(hereinafter, referred to as the inventive compound 117) .
Figure imgf000256_0001
Inventive compound 117
1 H-NMR (DMSO-D6) δ: 9.01 (s, 1H) , 8.61 (d, 1H), 8.15 (d, 1H) , 7.99 (d, 1H), 7.54-7.50 (m, 1H) , 7.44 (s, 1H) , 7.25 (d, 1H) , 3.43-3.36 (m, 4H) , 1.90-1.84 (m, 4H)
Production Example 118
N' , N' -dimethyl-N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran-3- yl]-urea (hereinafter, referred to as the inventive compound 118) (0.1 g) was obtained according to the method described in Production Example 117 using
dimethylamine instead of pyrrolidine.
Figure imgf000257_0001
Inventive compound 118
1 H-NMR (DMSO-D6) δ: 9.01 (s, 1H) , 8.61 (d, 1H) , 8.15 1H), 7.95 (d, 1H), 7.70 (s, 1H) , 7.55-7.50 (m, 1H) , 7 (d, 1H) , 2.96 (s, 6H)
Production Example 119
N' -ethyl-N' -methyl-N- [2-oxo-6- (pyridin-3-yl ) -2H- pyran-3-yl ] -urea (hereinafter, referred to as the inventive compound 119) was obtained according to the method described in Production Example 117 using N- eth lmethylamine instead of pyrrolidine.
Figure imgf000257_0002
Inventive compound 119
1 H-NMR (DMSO-D6) δ: 9.01 (s, 1H) , 8.61 (d, 1H), 8.16 (d, 1H) , 7.95 (d, 1H) , 7.64 (s, 1H) , 7.52 (dd, 1H), 7.25 (d, 1H) , 3.39-3.34 (m, 2H) , 2.96 (s, 3H) , 1.09 (t, 3H)
Production Example 120
N ' ,Ν' -diethyl-N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran-3- yl]-urea (hereinafter, referred to as the inventive compound 120) was obtained according to the method described in Production Example 117 using diethylamine instead of rrolidine
Figure imgf000258_0001
Inventive compound 120
1 H-NMR (DMSO-D6) δ: 9.01 (d, 1H) , 8.61 (dd, 1H), 8.17- 8.14 (m, 1H) , 7.95 (d, 1H) , 7.56 (s, 1H) , 7.52 (dd, 1H) , 7.25 (d, 1H) , 3.36 (q, 4H), 'l.l3 (t, 6H)
Production Example 121
N' - ( 2-methoxyethyl ) -N' -methyl-N- [2-oxo-6- (pyridin-3- yl ) -2H-pyran-3-yl ] -urea (hereinafter, referred to as the inventive compound 121) was obtained according to the method described in Production Example 117 using N-(2- methoxyethyl ) methylamine instead of pyrrolidine.
Figure imgf000258_0002
Inventive compound 121
1 H-NMR (DMSO-D6) δ: 9.00 (d, 1H) , 8.60 (d, 1H), 8.43 (br s, 1H), 8.14 (d, 1H), 7.88 (d, 1H) , 7.52 (dd, 1H) , 7.23 (d, 1H) , 3.56-3.45 (m, 4H) , 3.35 (s, 3H) , 2.94 (s, 3H)
Production Example 122
N- [2-OXO-6- (pyridin-3-yl ) -2H-pyran-3-yl ] -1- piperidine carboxamide (hereinafter, referred to as the inventive compound 122) was obtained according to the method described in Production Example 117 using
piperidine instead of pyrrolidine.
Figure imgf000259_0001
Inventive compound 122
1 H-NMR (DMSO-D6) δ: 9.01 (d, 1H) , 8.61 (dd, 1H) , 8.17-
8.14 (m, 1H) , 7.98 (s, 1H) , 7.90 (d, 1H) , 7.52 (dd, 1H) , 7.23 (d, 1H) , 3.43-3.38 (m, 4H) , 1.60-1.47 (m, 6H)
Production Example 123
N' , 1ST -dipropyl-N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran-3 yl]-urea (hereinafter, referred to as the inventive compound 123) was obtained according to the method described in Production Example 117 using dipropylamine instead of pyrrolidine.
Figure imgf000259_0002
Inventive compound 123
1 H-NMR (DMSO-D6) δ: 9.01 (s, 1H) , 8.61 (d, 1H), 8.15 (d,
1H), 7.93 (d, 1H), 7..57 (s, 1H) , 7.52 (dd, 1H), 7.25 (d,
1H) , 3.26 (t, 4H) , 1.61-1.52 (m, 4H) , 0.88 (t, 6H)
Production Example 124
N ' -methyl-N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran- 3-yl ] - urea (hereinafter, referred to as the inventive compound 124) was obtained according to the method described in Production Example 117 using methylamine instead of pyrrolidine .
Figure imgf000260_0001
Inventive compound 124
1 H-NMR (DMSO-D6) δ: 8.99 (d, 1H) , 8.60-8.58 (m, 2H) , 8.13 (d, 1H) , 8.04 (d, 1H) , 7.51 (dd, 1H) , 7.23 (d, 1H) , 6.93-6.89 (m, 1H) , 2.66 (d, 3H)
Production Example 125
N' ,Ν' -diisopropyl-N- [2-oxo-6- (pyridin-3-yl) -2H- pyran-3-yl ] -urea (hereinafter, referred to as the inventive compound 125) was obtained according to the method described in Production Example 117 using
diisopropylamine instead of pyrrolidine.
Figure imgf000260_0002
Inventive compound 125
1 H-NMR (DMSO-D6) δ: 9.00 (d, 1H) , 8.61 (d, 1H) , 8.15 (d, 1H), 7.96 (d, 1H) , 7.52 (dd, 1H) , 7.43 (s, 1H), 7.25 (d, 1H) , 4.03-3.97 (m, 2H) , 1.26 (d, 12H) Production Example 126
NT -methyl-N- [2-oxo-6- ( pyridin- 3-yl ) -2H-pyran-3-yl ] - N' -isopropyl-urea (hereinafter, referred to as the inventive compound 126) was obtained according to the method described in Production Example 117 using N- meth lisopropylamine instead of pyrrolidine.
Figure imgf000261_0001
Inventive compound 126
1 H-NMR (DMSO-D6) δ: 9.01 (d, 1H) , 8.61 (d, 1H) , 8.15 (d,
1H), 7.96 (d, 1H), 7.62 (s, 1H) , 7.52 (dd, 1H), 7.25 (d,
1H) , 4.46-4.39 (m, 1H) , 2.82 (s, 3H) , 1.10 (d, 6H)
Production Example 127
N- [2-OXO-6- (pyridin-3-yl) -2H-pyran-3-yl ] -4- morpholine carboxamide (hereinafter, referred to as the inventive compound 127) was obtained according to the method described in Production Example 117 using
morpholine instead of pyrrolidine.
Figure imgf000261_0002
Inventive compound 127
1 H-NMR (DMSO-D6) 5:9.01 (d, 1H) , 8.61 (d, 1H) , 8.18-8.12
(m, 2H) , 7.92 (d, 1H) , 7.52 (dd, 1H) , 7.24 (d, 1H) ,
3.63-3.59 (m, 4H) , 3.44-3.40 (m, 4H) Production Example 128
N- [2-OXO-6- (pyridin-3-yl) -2H-pyran-3-yl ] -4- thiomorpholine carboxamide (hereinafter, referred to as the inventive compound 128) was obtained according to the method described in Production Example 117 using thiomorpholine instead of pyrrolidine.
Figure imgf000262_0001
Inventive compound 128
1 H-NMR (DMS0-D6) δ: 9.01 (d, 1H) , 8.62 (d, 1H), 8.18- 8.14 (m, 2H), 7.87 (d, 1H) , 7.52 (dd, 1H) , 7.23 (d, 1H) , 3.74-3.69 (m, 4H) , 2.64-2.60 (m, 4H)
Production Example 129
N' -ethyl-N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] - urea (hereinafter, referred to as the inventive compound 129) was obtained according to the method described in Production Example 117 using ethylamine instead of pyrrolidine .
Figure imgf000262_0002
Inventive compound 129
1 H-NMR (DMSO-D6) δ: 8.99 (s, 1H) , 8.59 (d, 1H), 8.51 (s, 1H), 8.13 (d, 1H), 8.04 (d, 1H) , 7.51 (dd, 1H), 7.22 (d, 1H) , 7.05-7.01 (m, 1H) , 3.15-3.08 (m, 2H) , 1.05 (t, 3H)
Production Example 130
N- [2-OXO-6- (pyridin-3-yl) -2H-pyran-3-yl ] -N' - cyclopropyl-urea (hereinafter, referred to as the inventive compound 130) was obtained according to the method described in Production Example 117 using cyclopropylamine instead of pyrrolidine.
Figure imgf000263_0001
Inventive compound 130
1 H-NMR (DMSO-D6) δ : 8.99 (d, 1H) , 8.59 (d, 1H), 8.41 (b s, 1H) , 8.13 (d, 1H) , 8.04 (d, 1H) , 7.51 (dd, 1H) , 7.25 7.21 (m, 2H), 2.57-2.52 (m, 1H) , 0.67-0.62 (m, 2H) , 0.41-0.36 (m, 2H)
Production Example 131
N' -ethyl-N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] - N' -isopropyl-urea (hereinafter, referred to as the inventive compound 131) was obtained according to the method described in Production Example 117 using N- eth lisopropylamine instead of pyrrolidine.
Figure imgf000263_0002
Inventive compound 131 1 H-NMR (D SO-D6) δ: 9.01 (s, 1H) , 8.61 (d, 1H), 8.15 (d, 1H) , 7.97 (d, 1H) , 7.55-7.49 (m, 2H) , 7.25 (d, 1H) , 4.41-4.32 (m, 1H) , 3.33-3.26 (m, 2H) , 1.22-1.10 (m, 9H)
Production Example 132
N' -ethyl-N- [2-oxo-6- (pyridin-3-yl) -2H-pyran-3-yl] - N' -propyl-urea (hereinafter, referred to as the
inventive compound 132) was obtained according to the method described in Production Example 117 using N- eth lpropylamine instead of pyrrolidine.
Figure imgf000264_0001
Inventive compound 132
1 H-NMR (DMSO-D6) δ: 9.00 (s, 1H) , 8.61 (d, 1H) , 8.15 (d, 1H) , 7.94 (d, 1H) , 7.56-7.50 (m, 2H) , 7.25 (d, 1H) , 3.39-3.22 (m, 4H) , 1.61-1.52 (m, 2H), 1.13 (t, 3H) , 0.89 (t, 3H)
Production Example 133
N' -sec-butyl-N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran-3- yl] -urea (hereinafter, referred to as the inventive compound 133) was obtained according to the method .
described in Production Example 117 using see-butylamine instead of pyrrolidine.
Figure imgf000265_0001
Inventive compound 133
1 H-NMR (DMSO-D6) δ: 8.99 (s, 1H), 8.59 (d, 1H), 8.46 (s, 1H) , 8.13 (d, 1H) , 8.03 (d, 1H), 7.53-7.48 (m, 1H) , 7.22 (d, 1H) , 6.97 (d, 1H) , 3.63-3.55 (m, 1H) , 1.45-1.36 (m, 2H) , 1.06 (d, 3H) , 0.87 (t, 3H)
Production Example 134
N' -allyl-N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] - urea (hereinafter, referred to as the inventive compound 134) was obtained according to the method described in Production Example 117 using allylamine instead of pyrrolidine .
Figure imgf000265_0002
Inventive compound 134
1 H-NMR (DMSO-D6) δ: 8.99 (s, 1H) , 8.66. (s, 1H), 8.59 (d, 1H) , 8.13 (d, 1H) , 8.04 (d, 1H), 7.51 (dd, 1H), 7.23 (d, 1H) , 7.19-7.15 (m, 1H) , 5.92-5.81 (m, 1H) , 5.18 (d, 1H) , 5.09 (d, 1H) , 3.77-3.72 (m, 2H)
Production Example 135
N- [2-ΟΧΟ-6- (pyridin-3-yl) -2H-pyran-3-yl ] -N ' - cyclopropanemethyl-urea (hereinafter, referred to as the inventive compound 135) was obtained according to the method described in Production Example 117 using
cyclopropanemethylamine instead of pyrrolidine.
Figure imgf000266_0001
Inventive compound
1 H-NMR (DMSO-D6) δ: 8.99 (s, 1H) , 8.56-8.60 (m, 2H) , 8.13 (d, 1H) , 8.03 (d, 1H) , 7.51 (dd, 1H) , 7.22 (d, 1H) , 7.17 (t, 1H) , 3.01-2.96 (m, 2H), 0.96-0.88 (m, 1H) , 0.46-0.41 (m, 2H) , 0.20-0.15 (m, 2H)
Production Example 136
N- [2-OXO-6- (pyridin-3-yl) -2H-pyran-3-yl ] -N' - isopropyl-urea (hereinafter, referred to as the
inventive compound 136) was obtained according to the method described in Production Example 117 using
isopropylamine instead of pyrrolidine.
Figure imgf000266_0002
Inventive compound 136
1 H-NMR (DMS0-D6) δ: 8.98 (d, 1H), 8.59 (d, 1H) , 8.43 (s, 1H), 8.13 (d, 1H), 8.03 (d, 1H), 7.51 (dd, 1H) , 7.22 (d, 1H),7.00 (d, 1H) , 3.78-3.70 (m, 1H) , 1.09 (d, 6H)
Production Example ' -methyl-N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran- 3-yl ] - ' -phenyl-urea (hereinafter, referred to as the
inventive compound 137) was obtained according to the method described in Production Example 117 using N- methylaniline instead of pyrrolidine.
Figure imgf000267_0001
Inventive compound 137
1 H-NMR (DMSO-D6) δ: 8.97 (d, 1H), 8.60 (dd, 1H) , 8.12 8.09 (m, 1H), 8.03 (d, 1H) , 7.57-7.43 (m, 6H) , 7.27-7 (m, 2H) , 3.26 (s, 3H)
Production Example 138
N' -cyclohexyl- ' -methyl-N- [2-oxo-6- (pyridin-3-yl ) 2H-pyran-3-yl ] -urea (hereinafter, referred to as the inventive compound 138) was obtained according to the method described in Production Example 117 using N- methylcyclohexylamine instead of pyrrolidine.
Figure imgf000267_0002
Inventive compound 138
1 H-NMR (DMSO-D6) δ: 9.01 (d, 1H) , 8.61 (dd, 1H) , 8.17- 8.14 (m, 1H) , 7.95 (d, 1H) , 7.63 (s, 1H), 7.52 (dd, 1H), 7.25 (d, 1H) , 4.03-3.94 (m, 1H) , 2.85 (s, 3H) , 1.81-1.74 (m, 2H) , 1.64-1.55 (m, 3H) , 1.51-1.40 (m, 2H) , 1.37-1.25 (m, 2H) , 1.16-1.05 (m, 1H)
Production Example 139
N- [2-OXO-6- (pyridin-3-yl ) -2H-pyran-3-yl ] -N' -propyl- urea (hereinafter, referred to as the inventive compound 139) was obtained according to the method described in Production Example 117 using propylamine instead of pyrrolidine .
Figure imgf000268_0001
Inventive compound 139
1 H-NMR (DMSO-D6) δ: 8.98 (s, 1H) , 8.62-8.51 (m, 2H) , 8.13 (d, 1H) , 8.03 (d, 1H) , 7.54-7.49 (m, 1H) , 7.22 (d, 1H) , 7.08 (s, 1H) , 3.10-3.02 (m, 2H) , 1.49-1.40 (m, 2H) , 0.92-0.85 (m, 3H)
Production Example 140
N' -benzyl-N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] - N' -isopropyl-urea (hereinafter, referred to as the inventive compound 140) was obtained according to the method described in Production Example 117 using N- isopropylbenzylamine instead of pyrrolidine.
H3C CH3 Inventive compound 140
1 H-NMR (DMSO-D6) δ: 8.97 (d, 1H) , 8.60 (dd, 1H) , 8.13- 8.09 (m, 1H) , 7.97 (d, 1H) , 7.53-7.48 (m, 2H) , 7.39-7.31 (m, 4H) , 7.29-7.21 (m, 2H) , 4.57-4.47 (m, 3H) , 1.16 (d,
6H)
Production Example 141
N' -methyl-N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] - N ' -cyclopentyl-urea (hereinafter, referred to as the inventive compound 141) was obtained according to the method described in Production Example 117 using N- methylcyclopentylamine instead of pyrrolidine.
Figure imgf000269_0001
Inventive compound 141
1 H-NMR (DMSO-D6) δ: 9.01 (d, 1H) , 8.61 (dd, 1H) , 8.18- 8.14 (m, 1H) , 7.96 (d, 1H) , 7.66 (s, 1H) , 7.52 (dd, 1H) , 7.25 (d, 1H) , 4.61-4.52 (m, 1H) , 2.85 (s, 3H) , 1.80-1.62 (m, 4H), 1.58-1.47 (m, 4H)
Production Example 142
N' -benzyl-N' -ethyl-N- [2-oxo-6- (pyridin-3-yl ) -2H- pyran-3-yl ] -urea (hereinafter, referred to as the inventive compound 142) was obtained according to the method described in Production Example 117 using N- ethylbenzylamine instead of pyrrolidine.
Figure imgf000270_0001
Inventive compound 142
1 H-NMR (DMSO-D6) δ: 9.00 (d, 1H) , 8.61 (dd, 1H) , 8.17- 8.13 (m, 1H) , 7.97 (d, 1H) , 7.68 (s, 1H) , 7.52 (dd, 1H) , 7.39-7.23 (m, 6H) , 4.58 (s, 2H) , 3.41 (q, 2H) , 1.12 (t,
3H)
Production Example 143
N' -methyl-N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] - N' -2-propynyl-urea (hereinafter, referred to as the inventive compound 143) was obtained according to the method described in Production Example 117 using N- methyl-2-propynylamine instead of pyrrolidine.
Figure imgf000270_0002
Inventive compound 143
1 H-NMR (DMSO-D6) δ: 9.02 (d, 1H) , 8.62 (d, 1H), 8.16 (d, 1H) , 7.95-7.90 (m, 2H) , 7.55-7.50 (m, 1H) , 7.25 (d, 1H) , 4.19 (d, 2H) , 3.31-3.27 (m, 1H), 3.01 (s, 3H)
Production Example 144
N' -benzyl-N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] - urea (hereinafter, referred to as the inventive compound 144) was obtained according to the method described in Production Example 117 using benzylamine instead of pyrrolidine .
Figure imgf000271_0001
Inventive compound 144
1 H-NMR (D SO-D6) δ: 8.99 (d, 1H) , 8.68 (s, 1H), 8.59
(dd, 1H) , 8.15-8.11 (m, 1H) , 8.05 (d, 1H) , 7.54-7.49 (m,
2H), 7.37-7.22 (m, 6H) , 4.32 (d, 2H)
Production Example 145
N'-4-chlorobenzyl-N- [2-oxo-6- (pyridin-3-yl) -2H- pyran-3-yl ] -urea (hereinafter, referred to as the inventive compound 145) was obtained according to the method described in Production Example 117 using 4- chlorobenz lamine instead of pyrrolidine.
Figure imgf000271_0002
Inventive compound 145
1 H-NMR (DMSO-D6) δ: 8.99 (s, 1H) , 8.70 (s, 1H) , 8.59 (d, 1H), 8.15-8.12 (m, 1H) , 8.04 (d, 1H) , 7.54-7.50 (m, 2H) , 7.41 (d, 2H), 7.32 (d, 2H) , 7.23 (d, 1H) , 4.31 (d, 2H)
Production Example
N' -3-chlorobenzyl-N- [2-oxo-6- (pyridin-3-yl ) -2H- pyran-3-yl ] -urea (hereinafter, referred to as the inventive compound 146) was obtained according to the method described in Production Example using 3- chlorobenzylamine instead of pyrrolidine.
Figure imgf000272_0001
Inventive compound
1 H-NMR (DMSO-D6) δ: 8.99 (s, 1H) , 8.72 (s, 1H), 8.59 (d, 1H) , 8.14 (d, 1H) , 8.04 (d, 1H), 7.58-7.50 (m, 2H) , 7.40-7.30 (m, 3H) , 7.28-7.21 (m, 2H) , 4.33 (d, 2H) Production Example 147
N' -2-chlorobenzyl-N- [2-oxo-6- (pyridin-3-yl ) -2H- pyran-3-yl ] -urea (hereinafter, referred to as the inventive compound 147) was obtained according to the method described in Production Example 117 using 2- chlorobenzylamine instead of pyrrolidine.
Figure imgf000272_0002
Inventive compound 147
1 H-NMR (DMSO-D6) δ: 8.99 (s, 1H) , 8.79 (s, 1H), 8.59 (d, 1H) , 8.13 (d, 1H) , 8.04 (d, 1H) , 7.62-7.56 (m, 1H) , 7.54-7.45 (m, 2H) , 7.42 -7.29 (m, 3H) , 7.22 (d, 1H) , 4.38 (d, 2H)
Production Example N' -4-fluorobenzyl-N- [2-oxo-6- (pyridin-3-yl ) -2H- pyran-3-yl ] -urea (hereinafter, referred to as the inventive compound 148) was obtained according to the method described in Production Example 117 using 4- fluorobenzylamine instead of pyrrolidine.
Figure imgf000273_0001
Inventive compound 148
1 H-NMR (DMS0-D6) δ: 8.99 (s, 1H) , 8.68 (s, 1H) , 8.59 (d, 1H) , 8.13 (d, 1H), 8.05 (d, 1H) , 7.55-7.48 (m, 2H) , 7.37-7.30 (m, 2H) , 7.26-7.14 (m, 3H) , 4.30 (d, 2H)
Production Example 149
N' -3-fluorobenzyl-N- [2-oxo-6- (pyridin-3-yl ) -2H- pyran-3-yl ] -urea (hereinafter, referred to as the inventive compound 149) was obtained according to the method described in Production Example 117 using 3- fluorobenzylamine instead of pyrrolidine.
Figure imgf000273_0002
Inventive compound 149
1 H-NMR (DMSO-D6) δ: 8.99 (s, 1H) , 8.72 (s, 1H) , 8.59 (d, 1H) , 8.14 (d, 1H), 8.05 (d, 1H), 7.59-7.49 (m, 2H) , 7.43-7.36 (m, 1H) , 7.23 (d, 1H) , 7.17-7.06 (m, 3H) , 4.34 (d, 2H) Production Example 150
To 1.5 ml of DMF was added 0.2 g of N' , N' -dimethyl- N- [2-OXO-6- (pyridin-3-yl) -2H-pyran-3-yl] -urea, 0.03 g of sodium hydride(60% oily) and 0.1 g of Ν,Ν,Ν,Ν- tetramethyl- 1 , 2 -ethylenediamine , and the mixture was stirred with heating at 60°C for 10 hours. After
standing to cool, the mixture was poured into water, and the resultant mixture was extracted three times with ethyl acetate, and the organic layers were combined and dried over anhydrous magnesium sulfate, then,
concentrated. The residue was subjected to silica gel column chromatography to obtain 0.1 g of N' , N' -dimethyl- N- [2-OXO-6- (pyridin-3-yl ) -2H-pyran-3-yl ] -N- cyclopropanecarbonyl-urea (hereinafter, referred to as the inventive compound 150).
Figure imgf000274_0001
Inventive compound 150
1 H-NMR (D SO-D6) δ: 9.09 (d, 1H) , 8.70 (dd, 1H) , 8.27- 8.24 (m, 1H) , 7.78 (d, 1H) , 7.58 (dd, 1H) , 7.29 (d, 1H) , 2.97 (s, 6H) , 1.87-1.81 (m, 1H), 0.94-0.85 (m, 4H)
Production Example 151
N- [2-OXO-6- (pyridin-3-yl) -2H-pyran-3-yl ] -N ' - phenetyl-urea (hereinafter, referred to as the inventive compound 151) was obtained according to the method described in Production Example 117 using phenetylamine instead of pyrrolidine.
Figure imgf000275_0001
Inventive compound 151
1 H-NMR (DMSO-D6) δ: 8.98 (d, 1H) , 8.61 (s, 1H) , 8.59 (dd, 1H) , 8.15-8.10 (m, 1H) , 8.05 (d, 1H) , 7.51 (dd, 1H) , 7.34-7.30 (m, 2H) , 7.27-7.20 (m, 4H) , 7.08(t, 1H) , 3.39-3.34 (m, 2H) , 2.74 (t, 2H)
Production Example 152
N' -2-fluorobenzyl-N- [2-oxo-6- (pyridin-3-yl ) -2H- pyran-3-yl ] -urea (hereinafter, referred to as the inventive compound 152) was obtained according to the method described in Production Example 117 using 2- fluorobenzylamine instead of pyrrolidine.
Figure imgf000275_0002
Inventive compound 152
1 H-NMR (DMS0-D6) δ: 8.99 (s, 1H) , 8.71 (s, 1H) , 8.59 (d,
1H) , 8.15-8.11 (m, 1H) , 8.04 (d, 1H) , 7.56-7.49 (m, 2H) ,
7.39-7.31 (m, 2H) , 7.23-7.18 (m, 3H) , 4.36 (d, 2H)
Production Example 153 N' -butyl-N- [ 2-OXO-6- (pyridin-3-yl)-2H-pyran-3-yl]- urea (hereinafter, referred to as the inventive compound 153) was obtained according to the method described in Production Example 117 using butylamine instead of pyrrolidine .
Figure imgf000276_0001
Inventive compound 153
1 H-NMR (DMSO-D6) δ: 8.99 (s, 1H) , 8.59 (d, 1H), 8.53 (s, 1H) , 8.13 (d, 1H) , 8.03 (d, 1H) , 7.51 (dd, 1H) , 7.22 (d, 1H), 7.07-7.03 (m, 1H) , 3.09 (q, 2H) , 1.44-1.27 (m, 4H) , 0.89 (t, 3H)
Production Example 154
N- [2-OXO-6- (pyridin-3-yl) -2H-pyran-3-yl ] -N' -pentyl- urea (hereinafter, referred to as the inventive compound 154) was obtained according to the method described in Production Example .117 using pentylamine instead of pyrrolidine .
Figure imgf000276_0002
Inventive compound 154
1 H-NMR (DMSO-D6) δ: 8.99 (s, 1H) , 8.59 (d, 1H), 8.53 (s, 1H) , 8.13 (d, 1H), 8.03 (d, 1H), 7.53-7.48 (m, 1H) , 7.22 (d, 1H) , 7.08-7.02 (m, 1H) , 3.12-3.05 (m, 2H) , 1.46-1.37 (m, 2H) , 1.34-1.25 (m, 4H) , 0.88 (t, 3H)
Production Example 155
N' -allyl-N' -methyl-N- [2-oxo-6- (pyridin-3-yl ) -2H- pyran-3-yl ] -urea (hereinafter, referred to as the inventive compound 155) was obtained according to the method described in Production Example 117 using N- methylallylamine instead of pyrrolidine.
Figure imgf000277_0001
Inventive compound 155
1 H-NMR (DMSO-D6) δ: 9.00 (s, 1H) , 8.61 (d, 1H) , 8.15 1H), 7.95 (d, 1H), 7.68 (s, 1H) , 7.54-7.50 (m, 1H) , 7 (d, 1H), 5.90-5.75 (m, 1H) , 5.25-5.18 (m, 2H) , 3.97 ( 2H) , 2.96 (s, 3H)
Production Example 156
N' -cyclobutyl-N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran- yl] -urea (hereinafter, referred to as the inventive compound 156) was obtained according to the method described in Production Example 117 using
cyclobutylamine instead of pyrrolidine.
Figure imgf000277_0002
Inventive compound 156 1 H-NMR (DMSO-D6) δ: 8.98 (s, 1H) , 8.59 (d, 1H), 8.43 (s, 1H) , 8.13 (d, 1H) , 8.01 (d, 1H) , 7.53-7.49 (m, 1H) , 7.34 (d, 1H) , 7.22 (d, 1H) , 4.16-4.05 (m, 1H) , 2.25-2.17 (m, 2H), 1.85-1.75 (m, 2H) , 1.68-1.57 (m, 2H)
Next, examples for producing production
intermediates of the above-described inventive compounds are shown. Production Example 157
To a mixture of 300 mg of N- [2-oxo-6- (pyridin-3-yl ) - 2H-pyran-3-yl ] -carbamic acid phenyl ester, 489 mg of glycine methyl ester hydrochloride and 1.95 ml of DMF, 394 mg of triethylamine was dropped at room temperature, and the mixture was stirred for 3 hours. Further, 122 mg of glycine methyl ester hydrochloride and 98 mg of triethylamine were additionally added, and the mixture was stirred for 10 hours.
Water was added, and the solid was filtrated by a glass filter, and the filtrated product was washed water and t-butyl methyl ether to obtain 118 mg of methoxycarbonylmethyl-N- [2-oxo-6- (pyridin-3-yl ) -2H- pyran-3-yl ] -urea (hereinafter, referred to as the inventive compound 157) .
Figure imgf000278_0001
Inventive compound 1H-NMR (DMSO-D6) δ: 8.99 (1H, s), 8.88 (1H, s), 8.60 (1H, d) , 8.14 (1H, d) , 8.02 (1H, d) , 7.53-7.50 (1H, m) , 7.44-7.41 (1H, m) , 7.22 (1H, d) , 3.93 (2H, d) , 3.66 (3H, s) .
Production Example 158
To a mixture of 635 mg of N-methyl-N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] -acetamide and 2 ml of water, 2 ml of concentrated hydrochloric acid was dropped. The mixture was stirred at 60°C for 2 hours, then, 1 ml of concentrated hydrochloric acid was
additionally added, and the mixture was stirred at 60°C for 1 hour. The reaction solution was treated with sodium hydroxide under ice cool to adjust its pH to 9, then, the solid was filtrated, and washed with water, and dried to obtain 416 mg of N- [ 2-oxo- 6- (pyridin-3-yl ) - 2H-pyran-3-yl ] -N-methylamine (hereinafter, referred to as the inventive compound 158) .
Figure imgf000279_0001
Inventive compound
-NMR (DMSO-D6) δ: 8.92 (1H, d) , 8.50-8.48 (1H,
8.05-8.02 (1H, m) , 7.46-7.43 (1H, m) , 7.14 (1H, d) ,
6.36-6.32 (1H, m) , 6.14 (1H, d) , 2.73 (3H, d) . Production Example 159
A mixture of 0.2 g of N- [2-oxo-6- (pyridin-3-yl) -2H- pyran-3-yl ] -N-methylamine , 0.259 g of 4- nitrophenylchloroformate and 2 ml of pyridine was stirred at room temperature for 2.5 hours and at 60°C for 1 hour. Under ice cool, 0.723 g of diethylamine was added, and the mixture was heated up to 80°C and further stirred for 1.5 hours. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate, and the organic phase was concentrated, then, subjected to silica gel column chromatography to obtain a solid which was then washed with t-butyl methyl ether, to obtain 0.136 mg of Ν' ,Ν' -diethyl-N-methyl-N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] -urea (hereinafter,
referred to as the inventive compound 159) .
Figure imgf000280_0001
Inventive compound 159
1H-NMR (D SO-D6) δ: 9.04 (1H, d) , 8.64 (1H, dd) , 8.20- 8.17 (1H, m) , 7.55-7.52 (1H, m) , 7.26 (1H, d) , 7.22 (1H, d) , 3.20 (4H, q) , 2.95 (3H, s), 1.03 (6H, t).
Production Example 160
N-ethyl-N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] - acetamide (hereinafter, referred to as the inventive compound 160) was obtained according to the method described in Production Example 83 using [2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] -acetamide instead of [2- oxo-6- (pyridin-3-yl ) -2H-pyran- 3-yl ] - cyclopropanecarboxamide, and using ethyl iodide instead of methyl iodide.
Figure imgf000281_0001
Inventive compound 160
1H-NMR (DMSO-D6) δ : 9.11 (1H, d) , 8.71-8.69 (1H, m) , 8.27 (1H, d) , 7.80 (1H, br s), 7.58 (1H, dd) , 7.29 (1H, d) , 3.71 (2H, br s), 1.89 (3H, s), 1.03 (3H, t). Production Example 161
N- [2-OXO-6- (pyridin-3-yl ) -2H-pyran-3-yl ] -N- ethylamine (hereinafter, referred to as the inventive compound 161) was obtained according to the method described in Production Example 158 using N-ethyl-N- [ 2- oxo-6- (pyridin-3-yl ) -2H-pyran- 3-yl ] -acetamide instead of N-methyl-N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] - acetamide .
Figure imgf000281_0002
Inventive compound 161
1H-NMR (CDC13) δ : 8.92 (1H, d) , 8.52 (1H, dd) , 8.01- (1H, m) , 7.34-7.31 (1H, m) , 6.72 (1H, d) , 6.07 (1H, 4.87 (1H, s), 3.19-3.13 (2H, m) , 1.32 (3H, t).
Production Example A mixture of 0.58 g of N- [ 2 -oxo- 6- (pyridin-3-yl ) -2H- pyran-3-yl ] -N-ethylamine, 725 mg of 4- nitrophenylchloroformate and 5.5 ml of pyridine was heated at 60°C for 3.5 hours. Diethylamine (1.692 g) was added at room temperature, further, the mixture was heated up to 90°C and stirred for 8 hours. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate, and the organic phase was concentrated, and subjected to silica gel
chromatography, to obtain 104 mg of N' , N' -diethyl-N- ethyl-N- [2 -oxo- 6- (pyridin-3-yl)-2H-pyran-3-yl]urea
(hereinafter, referred to as the inventive compound 162) .
Figure imgf000282_0001
Inventive compound 162
1H-NMR (DMSO-D6) δ: 9.06 (1H, d) , 8.66-8.64 (1H, m) , 8.22-8.20 (1H, m) , 7.54 (1H, d) , 7.35 (1H, d) , 7.23 (1H, d) , 3.43 (2H, q) , 3.13 (4H, q) , 1.08 (3H, t), 0.98 (6H, t) .
Production Example 163
A mixture of 0.5 g of 3-amino- 6- (pyridin-3-yl ) - pyran-2-one, 718 mg of 4 -nitrophenylchloroformate and 5.3 ml of pyridine was heated at 60°C for 5 hours. At room temperature, 3.96 g of 2,2,3,3,3- pentafluoropropylamine was added, and the mixture was stirred for 4 hours. The generated solid was washed with ethyl acetate to remove insoluble materials. The filtrate was concentrated, and the resultant solid was washed with hexane and t-butyl methyl ether, to obtain 225 mg of N λ -2 , 2 , 3 , 3 , 3-pentafluoropropyl-N- [ 2 -oxo- 6- (pyridin-3-yl ) -2H-pyran-3-yl ] -urea (hereinafter,
referred to as the inventive compound 163) .
Figure imgf000283_0001
Inventive compound 163
1H-NMR (D SO-D6) δ: 9.00 (1H, d) , 8.87 (1H, s), 8.60 (1H, dd) , 8.16-8.13 (1H, m) , 8.03 (1H, d) , 7.62-7.59 (1H, m) , 7.53-7.50 (1H, m) , 7.24 (1H, d) , 4.09-4.00 (2H, m) . Reference Production Example 1
To a mixture of 8.5 g of sodium carbonate, 3.2 g of sodium hydroxide, 100 ml of water, 100 ml of THF and 5.0 g of glycine was added 7.7 g of cyclopropanecarbonyl chloride at 0°C, then, the mixture was stirred at room temperature for 15 hours. Concentrated hydrochloric acid was added until pH of the mixture reached 2, and THF was distilled off under reduced pressure. To the residue was added 400 ml of ethyl acetate, and the mixture was stirred at room temperature for 3 hours.
The mixture was filtrated, and 50 ml of water was added to the filtrate, and this was extracted three times with ethyl acetate. The combined organic layers were dried over magnesium sulfate, and concentrated under reduced pressure to obtain 9.6 g of ( cyclopropanecarbonyl- amide ) -acetic acid.
Figure imgf000284_0001
1 H-NMR (D SO-D6) δ: 12.49 (1H, s), 8.40-8.35 (1H, m) , 3.76 (2H, d) , 1.66-1.59 (1H, m) , 0.66 (4H, d) .
Reference Production Example 2
( Cyclobutylcarbonylamino ) acetic acid was obtained according to the method described in Reference
Production Example 1 using cyclobutane carbonyl chloride instead of cyclopropanecarbonyl chloride.
Figure imgf000284_0002
1 H-NMR (DMSO-D6) δ: 12.47 (1H, s), 7.98-7.94 (1H, m) , 3.71 (2H, d) , 3.09-3.00 (1H, m) , 2.16-2.07 (2H, m) , 2.06-1.97 (2H, m) , 1.94-1.84 (1H, m) , 1.79-1.71 (1H, m) .
Reference Production Example 3
( Cyclopentylcarbonylamino ) acetic acid was obtained according to the method described in Reference
Production Example 1 using cyclopentane carbonyl
chloride instead of cyclopropanecarbonyl chloride.
Figure imgf000285_0001
1 H-N R (DMSO-D6) δ: 12.45 (1H, s), 8.08-8.03 (1H, m) , 3.71 (2H, d) , 2.64-2.57 (1H, m) , 1.78-1.69 (2H, m) , 1.66-1.57 (4H, m) , 1.53-1.46 (2H, m) .
Reference Production Example 4
( Cyclohexylcarbonylamino ) acetic acid was obtained according to the method described in Reference
Production Example 1 using cyclohexane carbonyl chloride instead of cyclopropanecarbonyl chloride.
Figure imgf000285_0002
1 H-NMR (DMSO-D6) δ: 12.44 (1H, s), 8.01-7.97 (1H, m) , 3.69 (3H, d) , 2.18-2.11 (1H, m) , 1.73-1.66 (4H, m) , 1.63-1.58 (1H, m) , 1.36-1.25 (2H, m) , 1.23-1.12 (2H, m
Reference Production Example 5
2-butenoylaminoacetic acid was obtained according the method described in Reference Production Example 1 using 2-butenoyl chloride instead of
cyclopropanecarbonyl chloride.
Figure imgf000285_0003
-NMR (DMSO-D6) δ: 12.52 (1H, s), 8.24-8.18 (1H,
68-6.58 (1H, m) , 6.00-5.94 (1H, m) , 3.80 (2H, d) 1.82-1.78 (3H, m) .
Reference Production Example 6
I sobutyrylamino-acetic acid was obtained according to the method described in Reference Production Example 1 using isobutyryl chloride instead of
cyclopropanecarbonyl chloride.
Figure imgf000286_0001
1 H-NMR (DMSO-D6) δ: 12.45 (1H, s), 8.08-8.02 (1H, m) , 3.71 (2H, d) , 2.45-2.37 (1H, m) , 1.00 (6H, d) .
Reference Production Example 7
Pivaloylamino-acetic acid was obtained according to the method described in Reference Production Example 1 using pivaloyl chloride instead of cyclopropanecarbonyl chloride .
Figure imgf000286_0002
1 H-NMR (DMSO-D6) δ: 7.81-7.76 (1H, m) , 3.68 (2H, d) , 1.10 (9H, s) .
Reference Production Example 8
[ ( 1-methylcyclohexanecarbonyl ) -amino] -acetic acid was obtained according to the method described in
Reference Production Example 1 using 1- methylcyclohexanecarbonyl chloride instead of cyclopropanecarbonyl chloride.
Figure imgf000287_0001
1 H-NMR (DMSO-D6) δ: 12.32 (1H, s), 7.82-7.77 (1H, m) , 3.69 (2H, d) , 1.98-1.89 (2H, m) , 1.47-1.31 (5H, m) , 1.21-1.12 (3H, m) , 1.05-1.02 (3H, m) .
Reference Production Example 9
[ (2-methylcyclohexanecarbonyl) -amino] -acetic
was obtained according to the method described in
Reference Production Example 1 using 2- methylcyclohexanecarbonyl chloride instead of
cyclopropanecarbonyl chloride.
Figure imgf000287_0002
1 H-NMR (DMSO-D6) δ: 12.54-12.34 (1H, m) , 8.11-8.06 (1H, m) , 3.72-3.69 (2H, m) , 1.82-1.74 (1H, m) , 1.70-1.61 (4H, m) , 1.55-1.46 (1H, m) , 1.37-1.27 (1H, m) , 1.24-1.12 (2H, m) , 0.96-0.88 (1H, m) , 0.83-0.78 (3H, m) .
Reference Production Example 10
[( 3-methylcyclohexanecarbonyl ) -amino] -acetic acid was obtained according to the method described in
Reference Production Example 1 using 3-methylcyclohexane carbonyl chloride instead of cyclopropanecarbonyl chloride .
Figure imgf000288_0001
1 H-NMR (DMSO-D6) δ: 12.42 (1H, s), 8.02-7.95 (1H, m) , 3.70 (2H, d) , 2.21-2.13 (1H, m) , 1.75-1.58 (3H, m) , 1.51-1.44 (1H, m) , 1.39-1.32 (1H, m) , 1.27-1.17 (2H, m) 1.02-0.91 (1H, m) , 0.89-0.84 (3H, m) , 0.84-0.75 (1H, m)
Reference Production Example 11
[ (4-methylcyclohexanecarbonyl) -amino] -acetic acid was obtained according to the method described in
Reference Production Example 1 using 4-methylcyclohexanecarbonyl chloride instead of
cyclopropanecarbonyl chloride.
Figure imgf000288_0002
1 H-NMR (DMSO-D6) δ: 12.38 (1H, br s), 8.03-7.94 (1H, m) 3.71-3.68 (2H, m) , 1.75-1.64 (3H, m) , 1.49-1.40 (2H, m) 1.36-1.27 (3H, m) , 0.90-0.84 (5H, m) .
Reference Production Example 12
A mixture of 30 g of 3-acetylpyridine and 60 g of N, -dimethylformamidedimethylacetal was stirred for 6 hours under reflux with heat. After cooling down to room temperature, the mixture was concentrated under reduced pressure. 3-dimethylamino-l- (pyridin-3-yl ) - propenone (43 g) was obtained.
Figure imgf000289_0001
1 H-N R (CDC13) δ: 9.09-9.07 (1H, m) , 8.68-8.65 (1H, m) , 8.19 (1H, dt), 7.85 (1H, d) , 7.38-7.34 (1H, m) , 5.68 (1H, d) , 3.19 (3H, s), 2.96 (3H, s).
Reference Production Example 13
3-dimethylamino-l- (pyridyl-3-yl ) -2-buten-l-one was obtained according to the method described in Reference Production Example 12 using 1 , 1-dimethoxy-N, N- dimethylethanamine instead of N,N- dimethylformamidedimethylaceta1.
Figure imgf000289_0002
1 H-NMR (CDCI3) δ: 9.05 (d, 1H) , 8.63 (dd, 1H) , 8.17-8.13 (m, 1H) , 7.33 (dd, 1H) , 5.62 (s, 1H) , 3.11 (s, 6H) , 2.68 (s, 3H)
Reference Production Example 14
1- ( 2-chloropyridin-3-yl ) -3-dimethylamino-propenone was obtained according to the method described in
Reference Production Example 12 using 3-acetyl-2- chloropyridine instead of 3 -acetylpyridine .
Figure imgf000289_0003
-NMR (CDCI3) δ: 8.41-8.39 (1H, m) , 7.79-7.72 (1H, 7.29-7.26 (2H, m) , 5.39 (1H, dj , 3.14 (3H, s), 2.91 (3H, s) .
Reference Production Example 15
1- ( 6-chloropyridin-3-yl ) -3-dimethylamino-propenone was obtained according to the method described in
Reference Production Example 12 using 3-acetyl-6- chloropyridine instead of 3-acetylpyridine.
Figure imgf000290_0001
1 H-NMR (CDC13) δ : 8.84-8.37 (1H, m) , 8.17-8.14 (1H, m) , 7.86-7.83 (1H, m) , 7.36 (1H, d) , 5.62 (1H, d) , 3.19 (3H, s) , 2.96 (3H, s) .
Reference Production Example 16
1- ( 5-chloropyridin-3-yl ) -3-dimethylamino-propenone was obtained according to the method described in
Reference Production Example 12 using 3-acetyl-5- bromopyridine instead of 3-acetylpyridine.
Figure imgf000290_0002
1 H-NMR (CDCI3) δ : 8.98-8.97 (1H, m) , 8.73-8.72 (1H, m) , 8.33-8.31 (1H, m) , 7.86 (1H, d) , 5.62 (1H, d) , 3.20 (3H, s) , 2.97 (3H, s) .
Reference Production Example 17
1- ( 5-chloropyridin-3-yl ) -3-dimethylamino-propenone was obtained according to the method described in
Reference Production Example 12 using 3-acetyl-5- chloropyridine instead of 3-acetylpyridine .
Figure imgf000291_0001
1 H-NMR (CDC13) δ: 8.94 (d, 1H) , 8.62 (dd, 1H) , 8.18-8.16 (m, 1H) , 7.87 (d, 1H) , 5.63 (d, 1H) , 3.20 (s, 3H) , 2.97 (s, 3H)
Reference Production Example 18
1- (5, 6-dichloropyridin-3-yl ) -3-dimethylamino- propenone was obtained according to the method described in Reference Production Example 12 using 3-acetyl-5 , 6- dichloropyridine instead of 3-acetylpyridine.
Figure imgf000291_0002
1 H-NMR (CDCI3) δ: 8.73 (d, 1H) , 8.27 (d, 1H) , 7.87 (df 1H) , 5.59 (d, 1H), 3.21 (s, 3H), 2.98 (s, 3H)
Reference Production Example 19
1- ( 5-phenylpyridin-3-yl ) -3-dimethylamino-propenone was obtained according to the method described in
Reference Production Example 12 using 3-acetyl-5- phenylpyridine instead of 3-acetylpyridine.
CH=CHN(CH3)2 1 H-NMR (CDC13) δ: 9.05-9.04 (1H, m) , 8.91-8.89 (1H, m) , 8.39-8.38 (1H, m) , 7.88 (1H, d) , 7.66-7.62 (2H, m) , 7.52-7.47 (2H, m) , 7.44-7.40 (1H, m) , 5.73 (1H, d) , 3.20 (3H, s) , 2.97 (3H, s) .
Reference Production Example 20
1- ( 4-trifluoromethylpyridin-3-yl ) -3-dimethylamino- propenone was obtained according to the method described in Reference Production Example 12 using l-(4- trifluoromethylpyridin-3-yl ) -ethanone instead of 3- acetylpyridine.
Figure imgf000292_0001
1 H-NMR (CDCI3) δ: 8.79-8.73 (2H, m) , 7.87 (1H, bs), 7.55 (1H, d) , 5.30 (1H, s), 3.14 (3H, s), 2.90 (3H, s).
Reference Production Example 21
A mixture of 0.3 g of 3-amino- 6- (pyridin-3-yl ) - pyran-2-one, 0.16 g of succinic anhydride and 10 ml of bromobenzene was stirred at 130°C for 6 hours. The mixture was cooled down to room temperature, and the precipitate was filtrated, and the filtrated precipitate was washed with 20 ml of hexane. This was dried under reduced pressure to obtain 0.34 g of N-[2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] -succinamic acid.
Figure imgf000293_0001
1 H-NMR (DMSO-D6) δ: 9.85 (1H, s), 9.03-9.01 (1H, m) , 8.64-8.61 (1H, m) , 8.25 (1H, d) , 8.19-8.15 (1H, m) , 7 (1H, dd) , 7.25 (1H, d) , 2.74-2.69 (2H, m) , 2.43-2.40 (2H, m) .
Reference Production Example 22
4- [2-OXO-6- (pyridin-3-yl ) -2H-pyran-3-ylcarbamoyl ] butyrylic acid was obtained according to the method described in Reference Production Example 21 using glutaric anhydride instead of succinic anhydride.
Figure imgf000293_0002
1 H-NMR (DMSO-D6) δ: 12.09 (1H, s), 9.76 (1H, s), 9.03- 9.01 (1H, m) , 8.63 (1H, d) , 8.27 (1H, d) , 8.17 (1H, d) , 7.53 (1H, dd) , 7.25 (1H, d) , 2.52-2.50 (2H, m) , 2.28- 2.23 (2H, m) , 1.82-1.74 (2H, m) .
Reference Production Example 23
To 6 ml of DMF was added 1.5 g of N- [ 4 -bromo-2 -oxo- 6- (pyridin-3-yl ) -2H-pyran-3-yl ] -N-cyclopropanecarbonyl- cyclopropanecarboxamide and 0.48 g of sodium azide, and the mixture was stirred at room temperature for 15 hours. This was poured into water, and the resultant mixture was extracted three times with ethyl acetate, and the organic layers were combined and dried over anhydrous magnesium sulfate, then, concentrated to obtain N- [ 4-azide-2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] - N-cyclopropanecarbonyl-cyclopropanecarboxamide as a coarse product. The coarse product was used in the subsequent reaction without purification.
Figure imgf000294_0001
1 H-NMR (D SO-D6) δ: 9.21 (d, 1H) , 8.75 (dd, 1H) , 8.39 8.36 (m, 1H) , 7.61 (dd, 1H) , 7.51 (s, 1H) , 2.35-2.29 2H) , 0.97-0.92 (m, 8H)
Next, formulation examples are shown. Parts are weight .
Formulation Example 1
Ten (10) parts of any one of the inventive compounds 1 to 163 was dissolved in a mixture of 35 parts of xylene and 35 parts of N , N-dimethyl formamide , and 14 parts of polyoxyethylene styryl phenyl ether and 6 parts of calcium dodecylbenzenesul fonate were added, and thoroughly stirred and mixed to obtain each 10%
emulsifiable concentrate. Formulation Example 2
Twenty (20) parts of any one of the inventive compounds 1 to 163 was added into a mixture of 4 parts of sodium laurylsulfate , 2 parts of calcium
ligninsulfonate, 20 parts of a synthetic hydrous silicon oxide fine powder and 54 parts of diatomaceous earth, and these were thoroughly stirred and mixed to obtain each 20% wettable powder.
Formulation Example 3
To 2 parts of any one of the inventive compounds 1 to 163 was added 1 part of a synthetic hydrous silicon oxide fine powder, 2 parts of calcium ligninsulfonate, 30 parts of bentonite and 65 parts of kaolin clay, and these were sufficiently stirred and mixed. Then, a suitable amount of water was added to the mixture, and the mixture was further stirred, granulated by a
granulator, and dried under ventilation to obtain each 2% granule.
Formulation Example 4
One part of any one of the inventive compounds 1 to 163 was dissolved in a suitable amount acetone, and to this was added 5 parts of a synthetic hydrous silicon oxide fine powder, 0.3 parts of PAP and 93.7 parts of Fubasami clay, and sufficiently stirred and mixed, and acetone was removed by distillation to obtain each 1% powder . Formulation Example 5
Ten (10) parts of any one of the inventive compounds 1 to 163, 35 parts of white carbon containing 50 parts of polyoxyethylene alkyl ether sulfate ammonium salt, and 55 parts of water were mixed, and finely pulverized by a wet pulverization method to obtain each 10%
formulation .
Formulation Example 6
Zero point one (0.1) part of any one of the
inventive compounds 1 to 163 was dissolved in 5 parts of xylene and 5 parts of trichloroethane , and this solution was mixed to 89.9 parts of deodorized kerosene, to obtain each 0.1% oil solution.
Formulation Example 7
Ten (10) mg of any one of the inventive compounds 1 to 163 was dissolved in 0.5 ml of acetone, and this solution was used to treat 5 g of an animal solid feedstuff powder (breeding-propagation solid feedstuff powder CE-2, manufactured by CLEA Japan Inc.), and mixed uniformly. Then, acetone was evaporated to dryness, to obtain each poison bait. Next, effectiveness of the inventive compound as an active ingredient of a pest control agent is shown by test examples.
Test Example 1 Formulations of the inventive compounds 1 to 17, 22, 26, 29 to 56, 58 to 102, 104 to 146, 148 to 157, 159 and 162 to 163 obtained by Formulation Example 5 were diluted with water so that the active ingredient
concentration was 500 ppm, to prepare drug solutions for test .
A cucumber seedling (second true leaf spreading stage) planted on a polyethylene cup was inoculated with about 30 Aphis gossypii, and one day after inoculation, 10 ml of the above-described drug solution for test was sprayed .
Five days after spraying, the insect number of living Aphis gossypii parasitic on the leaves of the cucumber was checked, and the control value was
calculated according to the following formula.
Control value (%) = { 1- (Cb*Tai ) / (CaixTb) } χ 100
Letters in the formula represent the following meanings .
Cb : insect number before treatment on non-treated area
Cai: insect number in observation on non-treated area
Tb: insect number before treatment on treated area Tai: insect number in observation on treated area
As a result, the treated areas treated by the spray solutions for test of the inventive compounds 1 to 17, 22, 26, 29 to 56, 58 to 102, 104 to 146, 148 to 157, 159 and 162 to 163 showed a control value of 90% or more. Test Example 2
Formulations of the inventive compounds 6, 7, 8, 10, 11, 12, 55, 67, 68, 75, 77, 83, 85, 86, 87, 91 and 92 obtained by Formulation Example 5 were diluted with water so that the active ingredient concentration was 500 ppm, to prepare drug solutions for test.
On a tomato seedling (third true leaf spreading stage) planted on a polyethylene cup, Bemisia tabaci adult insects were released and allowed to lay eggs for about 24 hours. The tomato seedling was kept in a greenhouse of for 8 days, and the above-described drug solution for test was sprayed in a proportion of 10 ml/cup onto larvae hatched from laid eggs, and kept in a greenhouse of 25°C. Seven days after, the number of third instar larvae on the tomato leaves was checked, and the control value was calculated according to the following formula.
Control value (%) = { 1- ( Cb Tai ) / (Cai * Tb ) } 100
Letters in the formula represent the following meanings .
Cb: insect number before treatment on non-treated area
Cai: insect number in observation on non-treated area
Tb: insect number before treatment on treated area Tai: insect number in observation on treated area
As a result, the treated areas treated by the spray solutions for test of the inventive compounds 6, 7, 8, 10, 11, 12, 55, 67, 68, 75, 77, 83, 85, 86, 87, 91 and 92 showed a control value of 90% or more. Industrial applicability
The inventive compound is useful since it has an excellent controlling effect on pests.

Claims

1. A pyrone compound represented by formula (1):
Figure imgf000300_0001
wherein,
Q1 represents an oxygen atom or sulfur atom,
n represents 0 or 1,
R1 , R2 , R3 and R4 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, C3-C6
alicyclic hydrocarbon group optionally substituted by at least one halogen atom, phenyl group optionally
substituted by at least one member selected from Group X, 5-membered heterocyclic group optionally substituted by at least one member selected from Group X, 6-membered heterocyclic group optionally substituted by at least one member selected from Group X, hydrogen atom, halogen atom, nitro group, cyano group, -L1 R9 or -C(=0)R10;
here, L1 represents an oxygen atom, -S(0)m- or - m represents 0, 1 or 2,
R9 represents a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, phenyl group optionally substituted by at least one member selected from Group X, 5-membered heterocyclic group optionally substituted by at least one member selected from Group X, 6-membered heterocyclic group optionally substituted by at least one member selected from Group X or hydrogen atom (with the proviso that R9 does not represent a hydrogen atom when L1 is -S(0)m- and m is 1 or 2 ) ,
R10 represents a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, Cl- C6 alkoxy group optionally substituted by at least one halogen atom, C1-C6 alkylamino group optionally
substituted by at least one halogen atom, C2-C8
dialkylamino group optionally substituted by at least one halogen atom, hydrogen atom, hydroxy group or amino group,
R11 represents a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, or hydrogen atom;
R5 and R6 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, C3-C6 alicyclic hydrocarbon group optionally substituted by at least one halogen atom, phenyl group optionally substituted by at least one member selected from Group X, 5-membered
heterocyclic group optionally substituted by at least one member selected from Group X, 6-membered
heterocyclic group optionally substituted by at least one member selected from Group X, hydrogen atom, halogen atom, nitro group, cyano group, -L2 R12 or -C(=0)R10, here, L represents' an oxygen atom, -S(0)m- or - NR13 - (m and R10 represent the same meaning as described above ) ,
R12 and R13 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted by at least one member selected from Group W, C3-C6 alicyclic hydrocarbon group optionally substituted by at least one member selected from Group a, phenyl group optionally substituted by at least one member selected from Group X, 5-membered heterocyclic group optionally substituted by at least one member selected from Group X, 6-membered heterocyclic group optionally substituted by at least one member selected from Group X, or
hydrogen atom (with the proviso that R12 does not represent a hydrogen atom when L2 is -S(0)m- and m is 1 or 2), alternatively, R12 and R13 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected;
R7 and R8 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted by at least one member selected from Group , hydrogen atom, or -L3 R14 , alternatively, R7 and R8 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected;
here, L3 represents -C(=Q3)- or -S(0)2-,
Q3 represents an oxygen atom or sulfur atom,
R14 represents a C1-C6 chain hydrocarbon group optionally substituted by at least one member selected from Group W, C3-C6 alicyclic hydrocarbon group
optionally substituted by at least one member selected from Group a, phenyl group optionally substituted by at least one member selected from Group X, 5-membered heterocyclic group optionally substituted by at least one member selected from Group X, 6-membered
heterocyclic group optionally substituted by at least one member selected from Group X, hydrogen atom or - L4 R15 (with the proviso that R14 does not represent a hydrogen atom when L3 is -S(0)2-; and except that -NR7R8 is -NHCOC6H5) ,
L4 represents an oxygen atom or -NR16-,
R15 and R16 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted by at least one member selected from Group W, C3-C6 alicyclic hydrocarbon group optionally substituted by at least one member selected from Group a, phenyl group optionally substituted by at least one member selected from Group X, 5-membered heterocyclic group optionally substituted by at least one member selected from Group X, 6-membered heterocyclic group optionally substituted by at least one member selected from Group X, or
hydrogen atom, alternatively, R15 and R16 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected;
Group X: the group consisting of C1-C4 alkyl groups optionally substituted by at least one halogen atom, Cl- C4 alkoxy groups optionally substituted by at least one halogen atom, cyano group, nitro group and halogen atoms;
Group Y: the group consisting of C1-C4 alkoxy groups optionally substituted by at least one halogen atom, Cl- C4 alkylthio groups optionally substituted by at least one halogen atom, benzyloxy group optionally substituted by at least one halogen atom, C2-C6 alkoxy groups optionally substituted by at least one halogen atom, cyano group and halogen atoms;
Group a: the group consisting of C1-C3 alkyl groups, C1-C4 alkoxy groups optionally substituted by at least one halogen atom, C1-C4 alkylthio groups optionally substituted by at least one halogen atom, cyano group and halogen atoms;
Group W: the group consisting of C1-C4 alkoxy groups optionally substituted by at least one halogen atom, Cl- C4 alkylthio groups optionally substituted by at least one halogen atom, benzyloxy group optionally substituted by at least one halogen atom, C2-C6 alkoxy groups optionally substituted by at least one halogen atom, cyano group, halogen atoms, C3-C6 alicyclic hydrocarbon groups optionally substituted by at least one member selected from Group a, phenyl groups optionally
substituted by at least one member selected from Group X, 5-membered heterocyclic groups optionally substituted by at least one member selected from Group X and 6- membered heterocyclic groups optionally substituted by at least one member selected from Group X.
2. The pyrone compound according to Claim 1, wherein Q1 is an oxygen atom, in formula (1) .
3. The pyrone compound according to Claim 1, wherein R2 is a C1-C6 chain hydrocarbon group optionally
substituted by at least one halogen atom, phenyl group optionally substituted by at least one member selected from Group X, hydrogen atom, halogen atom, nitro group, cyano group or -L1 R9 (here, L1 and R9 are the same meaning as defined in Claim 1) , in formula (1) .
4. The pyrone compound according to Claim 1, wherein R6 is a hydrogen atom, halogen atom, cyano group or -L2 R12
(here, L2 and R12 are the same meaning as defined in Claim 1), in formula (1).
5. The pyrone compound according to Claim 1, wherein R5 is a C1-C6 chain hydrocarbon group optionally
substituted by at least one halogen atom, hydrogen atom, halogen atom or -C(=0)R10 (here, R10 is the same meaning as defined in Claim 1), in formula (1).
6. The pyrone compound according to Claim 1, wherein R1 , R3 and R4 are the same or different and are a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, hydrogen atom, halogen atom, nitro group, cyano group or -L1 R9 (here, L1 and R9 are the same meaning as defined in Claim 1), in formula (1).
7. The pyrone compound according to Claim 1, wherein R1 , R3 , R4 and R5 are the same or different and are a C1-C6 chain hydrocarbon group optionally substituted by at least one halogen atom, hydrogen atom or halogen atom, in formula (1) .
8. The pyrone compound according to Claim 1, wherein R1 , R3 , R4 and R5 are hydrogen atoms, R2 is a hydrogen atom or halogen atom, and R6 is a hydrogen atom, halogen atom or -L2 R12 (here, L1 , R9 , L2 and R12 are the same meaning as defined in Claim 1) , in formula (1) .
9. The pyrone compound according to Claim 1, wherein
R1 , R2 , R3 , R , R5 and R6 are hydrogen atoms, in formula (1) .
10. The pyrone compound according to Claim 1, wherein R7 and R8 are the same or different and are a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group W, hydrogen atom or -L3 R14 , alternatively, R7 and R8 may be bound to form a 5- membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected,
R14 is a C1-C6 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group Z, C3-C6 alicyclic hydrocarbon group optionally substituted by at least one member selected from Group a, phenyl group optionally substituted by at least one member selected from Group X, 5-membered heterocyclic group optionally substituted by at least one member selected from Group X, 6-membered heterocyclic group optionally substituted by at least one member selected from Group X or -L4 R15 (with the proviso that compounds in which R7 is a hydrogen atom, R8 is -C(=0)R14 and R14 is a phenyl group are excluded) ,
R15 is a C1-C4 chain hydrocarbon group optionally substituted by at least one member selected from Group W, C3-C6 alicyclic hydrocarbon group optionally
substituted by at least one member selected from Group a, phenyl group optionally substituted by at least one member selected from Group X, 5-membered heterocyclic group optionally substituted by at least one member selected from Group X or 6-membered heterocyclic group optionally substituted by at least one member selected from Group X,
R16 is a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, or hydrogen atom, alternatively, R15 and R16 may be bound to form a 5-membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected
(here, L3 and L4 are the same meaning as defined in Claim 1 ) ,
Group Z: the group consisting of C3-C6 alicyclic hydrocarbon groups optionally substituted by at least one member selected from Group a, phenyl groups
optionally substituted by at least one member selected from Group X, 5-membered heterocyclic groups optionally substituted by at least one member selected from Group X and 6-membered heterocyclic groups optionally
substituted by at least one member selected from Group X,
in formula ( 1 ) .
11. The pyrone compound according to Claim 1, wherein R7 and R8 are the same or different and are a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, hydrogen atom or -L3 R14 , alternatively, R7 and R8 may be bound to form a 5- membered heterocyclic ring optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic ring optionally substituted by at least one member selected from Group Y together with the nitrogen atom to which they are connected,
Q3 is an oxygen atom,
R1 is a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, C3-C6 alicyclic hydrocarbon group optionally
substituted by at least one member selected from Group a, or -L4 R15 ,
R15 is a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group W or C3-C6 alicyclic hydrocarbon group optionally
substituted by at least one member selected from Group a,
R16 is a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y or hydrogen atom (here, L3 and L4 are the same meaning as defined in Claim 1) , in formula (1) .
12. The pyrone compound according to Claim 1, wherein R7 and R8 are the same or different and are a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, hydrogen atom or -L3 R14 , Q3 is an oxygen atom,
R14 is a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y, cyclopropyl group optionally substituted by at least one member selected from Group a or -L R15,
R15 is a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group W or cyclopropyl group optionally substituted by at least one member selected from Group a,
R16 is a C1-C3 chain hydrocarbon group optionally substituted by at least one member selected from Group Y or hydrogen atom (here, L3 and L4 are the same meaning as defined in Claim 1) , in formula (1) .
13. A pest control agent comprising the pyrone compound as described in Claim 1 and an inert carrier.
14. Use of the pyrone compound as described in Claim 1 for control pests.
15. A pest control method comprising applying an effective amount of the pyrone compound as described in Claim 1 to pests or areas where pests live.
16. N- [2-OXO-6- (pyridin-3-yl ) -2H-pyran-3-yl ] -acetamide
17. N- [2-OXO-6- (pyridin-3-yl) -2H-pyran-3-yl ] - cyclopropanecarboxamide
18. N-[2-oxo-6-(pyridin-3-yl)-2H-pyran-3-yl] -carbamic acid methyl ester
19. N-[2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl] -carbamic acid phenyl ester
20. N-acetyl-N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] - cyclopropanecarboxamide
21. N-acetyl-N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] - acetamide
22. N-methyl-N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] - cyclopropanecarboxamide
23. N-cyclopropanecarbonyl-N- [2-oxo-6- (pyridin-3-yl) -2H pyran-3-yl ] -cyclopropanecarboxamide
24. N-methyl-N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] - acetamide
25. N' ,Ν' -dimethyl-N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran-3 yl ] -urea
26. N' ,Ν' -diethyl-N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran-3- yl ] -urea
27. N' -methyl-N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] - urea
28. N' -ethy1-N- [2-oxo-6- (pyridin-3-yl ) -2H-pyran-3-yl ] - urea
PCT/JP2010/068538 2009-10-22 2010-10-14 Pyrone compound and its use for pest control WO2011049150A1 (en)

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014060381A1 (en) 2012-10-18 2014-04-24 Bayer Cropscience Ag Heterocyclic compounds as pesticides
WO2015040408A2 (en) * 2013-09-18 2015-03-26 Redx Pharma Limited Agricultural chemicals
CN111039810A (en) * 2019-12-13 2020-04-21 厦门蔚嘉制药有限公司 Preparation process of praziquantel intermediate
US11046658B2 (en) 2018-07-02 2021-06-29 Incyte Corporation Aminopyrazine derivatives as PI3K-γ inhibitors
US11926616B2 (en) 2018-03-08 2024-03-12 Incyte Corporation Aminopyrazine diol compounds as PI3K-γ inhibitors

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2016193834A (en) * 2013-07-17 2016-11-17 国立大学法人 鹿児島大学 Novel pyranone carboxamide derivative and use thereof as anti-hepatitis c virus agent

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06220036A (en) * 1992-09-10 1994-08-09 Bayer Ag 2-arylpyron derivative
JP2002527429A (en) * 1998-10-09 2002-08-27 バイエル アクチェンゲゼルシャフト 3-phenyl-pyrones
WO2009144935A1 (en) * 2008-05-28 2009-12-03 日本曹達株式会社 Nitrogenous heterocyclic compounds and fungicides for agricultural and horticultural use

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06220036A (en) * 1992-09-10 1994-08-09 Bayer Ag 2-arylpyron derivative
JP2002527429A (en) * 1998-10-09 2002-08-27 バイエル アクチェンゲゼルシャフト 3-phenyl-pyrones
WO2009144935A1 (en) * 2008-05-28 2009-12-03 日本曹達株式会社 Nitrogenous heterocyclic compounds and fungicides for agricultural and horticultural use

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
ABDEL, A. E.: "Studies With Quinolines: New Synthetic Routes to 4H, 5H, 6H, 9H-Benzo [ij] pyrano [ 2, 3-b ] quinolizine-8-one, 4H-Pyrano [2,3-b] pyridine, 2H -Pyran-2-one and Pyranopyridoquinoline Derivatives", J HETEROCYCL CHEM, vol. 42, no. 5, 2005, pages 943 - 946 *
ABDEL-MEGID, M.: "Substituted Quinolinones. Part 13 A Convenient Route to Heterocyclization Reactions with 3-Substituted 4-Hydroxyquinolin-2(lH)-one", J HETEROCYCL CHEM, vol. 44, no. 2, 2007, pages 315 - 322 *
DATABASE REGISTRY [online] 25 February 2003 (2003-02-25), "CN Benzamide, N-[2-oxo-6-(3-pyridinyl)-2H-pyran -3-yl]", retrieved from https://stnweb-japan.cas.org accession no. STN Database accession no. 494762-99-1 *
POZGAN, F.: "Synthesis of 2H-pyran-2-ones and fused pyran-2-ones as useful building blocks", ARKIVOC, 2007, GAINESVILLE,FL,UNITED STATES, pages 97 - 111 *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014060381A1 (en) 2012-10-18 2014-04-24 Bayer Cropscience Ag Heterocyclic compounds as pesticides
WO2015040408A2 (en) * 2013-09-18 2015-03-26 Redx Pharma Limited Agricultural chemicals
WO2015040408A3 (en) * 2013-09-18 2015-05-07 Redx Pharma Limited Agricultural chemicals
US11926616B2 (en) 2018-03-08 2024-03-12 Incyte Corporation Aminopyrazine diol compounds as PI3K-γ inhibitors
US11046658B2 (en) 2018-07-02 2021-06-29 Incyte Corporation Aminopyrazine derivatives as PI3K-γ inhibitors
CN111039810A (en) * 2019-12-13 2020-04-21 厦门蔚嘉制药有限公司 Preparation process of praziquantel intermediate

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