TW201136518A - Haloalkyl-substituted amides as insecticides and acaricides - Google Patents
Haloalkyl-substituted amides as insecticides and acaricides Download PDFInfo
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- TW201136518A TW201136518A TW099136408A TW99136408A TW201136518A TW 201136518 A TW201136518 A TW 201136518A TW 099136408 A TW099136408 A TW 099136408A TW 99136408 A TW99136408 A TW 99136408A TW 201136518 A TW201136518 A TW 201136518A
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- alkyl
- crc6
- alkoxy
- substituents
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- 239000002917 insecticide Substances 0.000 title claims abstract description 22
- 239000000642 acaricide Substances 0.000 title claims abstract description 4
- 230000000895 acaricidal effect Effects 0.000 title claims abstract 3
- 150000001408 amides Chemical class 0.000 title abstract description 5
- 238000000034 method Methods 0.000 claims abstract description 81
- 238000002360 preparation method Methods 0.000 claims abstract description 34
- 230000008569 process Effects 0.000 claims abstract description 25
- 229910052720 vanadium Inorganic materials 0.000 claims abstract description 4
- 229910052727 yttrium Inorganic materials 0.000 claims abstract description 4
- -1 alkylamino thiol Chemical class 0.000 claims description 381
- 125000001424 substituent group Chemical group 0.000 claims description 183
- 150000001875 compounds Chemical class 0.000 claims description 175
- 238000006243 chemical reaction Methods 0.000 claims description 144
- 229910052739 hydrogen Inorganic materials 0.000 claims description 108
- 239000001257 hydrogen Substances 0.000 claims description 105
- 125000000217 alkyl group Chemical group 0.000 claims description 104
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 91
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 86
- 229910052736 halogen Inorganic materials 0.000 claims description 83
- 150000002367 halogens Chemical class 0.000 claims description 83
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 78
- 150000001412 amines Chemical class 0.000 claims description 68
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 68
- 125000003118 aryl group Chemical group 0.000 claims description 57
- 125000003545 alkoxy group Chemical group 0.000 claims description 54
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 44
- 239000000126 substance Substances 0.000 claims description 44
- 125000001072 heteroaryl group Chemical group 0.000 claims description 39
- 239000007789 gas Substances 0.000 claims description 38
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 37
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 34
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 33
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 29
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 29
- 239000003795 chemical substances by application Substances 0.000 claims description 28
- 125000000623 heterocyclic group Chemical group 0.000 claims description 27
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 26
- 241001465754 Metazoa Species 0.000 claims description 24
- 229910052799 carbon Inorganic materials 0.000 claims description 23
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 23
- 241000607479 Yersinia pestis Species 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 21
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 20
- 125000003282 alkyl amino group Chemical group 0.000 claims description 20
- 239000000463 material Substances 0.000 claims description 19
- 125000003277 amino group Chemical group 0.000 claims description 18
- 238000004519 manufacturing process Methods 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 16
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 16
- 150000001721 carbon Chemical group 0.000 claims description 16
- 150000002576 ketones Chemical class 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 15
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 15
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000000468 ketone group Chemical group 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 238000006467 substitution reaction Methods 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 13
- 241000238631 Hexapoda Species 0.000 claims description 13
- 125000004414 alkyl thio group Chemical group 0.000 claims description 13
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 13
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 12
- 125000004104 aryloxy group Chemical group 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 11
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims description 11
- 239000000843 powder Substances 0.000 claims description 11
- 239000002689 soil Substances 0.000 claims description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 10
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 10
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 9
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 9
- 229930194542 Keto Natural products 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 239000008187 granular material Substances 0.000 claims description 9
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 9
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- 206010036790 Productive cough Diseases 0.000 claims description 8
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 8
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 8
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 229910052763 palladium Inorganic materials 0.000 claims description 8
- 208000024794 sputum Diseases 0.000 claims description 8
- 229910021653 sulphate ion Inorganic materials 0.000 claims description 8
- 239000005864 Sulphur Substances 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 210000004268 dentin Anatomy 0.000 claims description 7
- 239000000543 intermediate Substances 0.000 claims description 7
- 150000002632 lipids Chemical group 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 7
- 239000011734 sodium Substances 0.000 claims description 7
- 229910052708 sodium Inorganic materials 0.000 claims description 7
- 239000002023 wood Substances 0.000 claims description 7
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 6
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 6
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- LJSQFQKUNVCTIA-UHFFFAOYSA-N diethyl sulfide Chemical compound CCSCC LJSQFQKUNVCTIA-UHFFFAOYSA-N 0.000 claims description 6
- 150000004141 diterpene derivatives Chemical class 0.000 claims description 6
- 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 claims description 6
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 6
- ZNPKAOCQMDJBIK-UHFFFAOYSA-N nitrocyanamide Chemical group [O-][N+](=O)NC#N ZNPKAOCQMDJBIK-UHFFFAOYSA-N 0.000 claims description 6
- SFJGCXYXEFWEBK-UHFFFAOYSA-N oxazepine Chemical compound O1C=CC=CC=N1 SFJGCXYXEFWEBK-UHFFFAOYSA-N 0.000 claims description 6
- 229920000642 polymer Polymers 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 5
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 5
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims description 5
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims description 5
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 5
- 239000004606 Fillers/Extenders Substances 0.000 claims description 5
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 5
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 5
- ROPLCSFPUPWHGJ-UHFFFAOYSA-N hydroxycyanamide Chemical group ONC#N ROPLCSFPUPWHGJ-UHFFFAOYSA-N 0.000 claims description 5
- 239000012528 membrane Substances 0.000 claims description 5
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 5
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 210000003296 saliva Anatomy 0.000 claims description 5
- 238000003892 spreading Methods 0.000 claims description 5
- 230000007480 spreading Effects 0.000 claims description 5
- 210000003802 sputum Anatomy 0.000 claims description 5
- 239000004575 stone Substances 0.000 claims description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
- 238000003971 tillage Methods 0.000 claims description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 4
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 claims description 4
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 206010039424 Salivary hypersecretion Diseases 0.000 claims description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 230000004071 biological effect Effects 0.000 claims description 4
- 229920002678 cellulose Polymers 0.000 claims description 4
- 239000001913 cellulose Substances 0.000 claims description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- RNIXSZHNJLUJGC-UHFFFAOYSA-N hydroxy(nitro)cyanamide Chemical compound N#CN(O)[N+]([O-])=O RNIXSZHNJLUJGC-UHFFFAOYSA-N 0.000 claims description 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims description 4
- BUIMWOLDCCGZKZ-UHFFFAOYSA-N n-hydroxynitramide Chemical compound ON[N+]([O-])=O BUIMWOLDCCGZKZ-UHFFFAOYSA-N 0.000 claims description 4
- 150000002923 oximes Chemical class 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 4
- 150000003254 radicals Chemical class 0.000 claims description 4
- 208000026451 salivation Diseases 0.000 claims description 4
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 4
- WYRSGXAIHNMKOL-UHFFFAOYSA-N $l^{1}-sulfanylethane Chemical compound CC[S] WYRSGXAIHNMKOL-UHFFFAOYSA-N 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 3
- 125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 claims description 3
- OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 claims description 3
- 241000222552 Chickpea chlorosis virus Species 0.000 claims description 3
- 239000007983 Tris buffer Substances 0.000 claims description 3
- 150000003973 alkyl amines Chemical class 0.000 claims description 3
- 125000001769 aryl amino group Chemical group 0.000 claims description 3
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 claims description 3
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 3
- 125000006612 decyloxy group Chemical group 0.000 claims description 3
- 125000006001 difluoroethyl group Chemical group 0.000 claims description 3
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 3
- 238000001704 evaporation Methods 0.000 claims description 3
- 150000002366 halogen compounds Chemical class 0.000 claims description 3
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 claims description 3
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 3
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 3
- 230000036961 partial effect Effects 0.000 claims description 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000006337 tetrafluoro ethyl group Chemical group 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- 230000000007 visual effect Effects 0.000 claims description 3
- 125000001607 1,2,3-triazol-1-yl group Chemical group [*]N1N=NC([H])=C1[H] 0.000 claims description 2
- 125000001766 1,2,4-oxadiazol-3-yl group Chemical group [H]C1=NC(*)=NO1 0.000 claims description 2
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims description 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims description 2
- HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 claims description 2
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 2
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 claims description 2
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 2
- LSRGXLRLWFDKNR-UHFFFAOYSA-N FC(F)(F)[S] Chemical compound FC(F)(F)[S] LSRGXLRLWFDKNR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 2
- 125000003725 azepanyl group Chemical group 0.000 claims description 2
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 2
- 230000000739 chaotic effect Effects 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 238000003776 cleavage reaction Methods 0.000 claims description 2
- CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000006003 dichloroethyl group Chemical group 0.000 claims description 2
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 2
- 230000008020 evaporation Effects 0.000 claims description 2
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000006341 heptafluoro n-propyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)* 0.000 claims description 2
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
- 238000005304 joining Methods 0.000 claims description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
- 229960005181 morphine Drugs 0.000 claims description 2
- 125000006252 n-propylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 claims description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000000160 oxazolidinyl group Chemical group 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 125000003566 oxetanyl group Chemical group 0.000 claims description 2
- 125000000466 oxiranyl group Chemical group 0.000 claims description 2
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 claims description 2
- 125000005981 pentynyl group Chemical group 0.000 claims description 2
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 230000007017 scission Effects 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000006000 trichloroethyl group Chemical group 0.000 claims description 2
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 3
- 229910002651 NO3 Inorganic materials 0.000 claims 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 3
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 2
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 claims 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- 101150020251 NR13 gene Proteins 0.000 claims 2
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- PYNKFIVDSJSNGL-UHFFFAOYSA-N thiosultap Chemical compound OS(=O)(=O)SCC(N(C)C)CSS(O)(=O)=O PYNKFIVDSJSNGL-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- VJQYLJSMBWXGDV-UHFFFAOYSA-N tiadinil Chemical compound N1=NSC(C(=O)NC=2C=C(Cl)C(C)=CC=2)=C1C VJQYLJSMBWXGDV-UHFFFAOYSA-N 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
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- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical compound COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- WPALTCMYPARVNV-UHFFFAOYSA-N tolfenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(OC=3C=CC(C)=CC=3)=CC=2)=C1Cl WPALTCMYPARVNV-UHFFFAOYSA-N 0.000 description 1
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- 230000002588 toxic effect Effects 0.000 description 1
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- DDVNRFNDOPPVQJ-HQJQHLMTSA-N transfluthrin Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=C(F)C(F)=CC(F)=C1F DDVNRFNDOPPVQJ-HQJQHLMTSA-N 0.000 description 1
- 230000009261 transgenic effect Effects 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- JEMZVDDGSSQLRH-UHFFFAOYSA-N tributyl(4-cyclohexylbutyl)phosphanium Chemical compound C1(CCCCC1)CCCC[P+](CCCC)(CCCC)CCCC JEMZVDDGSSQLRH-UHFFFAOYSA-N 0.000 description 1
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- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
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- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
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- 229910052721 tungsten Inorganic materials 0.000 description 1
- 241001148471 unidentified anaerobic bacterium Species 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- JARYYMUOCXVXNK-CSLFJTBJSA-N validamycin A Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-CSLFJTBJSA-N 0.000 description 1
- DBXFMOWZRXXBRN-LWKPJOBUSA-N valifenalate Chemical compound CC(C)OC(=O)N[C@@H](C(C)C)C(=O)NC(CC(=O)OC)C1=CC=C(Cl)C=C1 DBXFMOWZRXXBRN-LWKPJOBUSA-N 0.000 description 1
- 230000009105 vegetative growth Effects 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- BCEHBSKCWLPMDN-MGPLVRAMSA-N voriconazole Chemical compound C1([C@H](C)[C@](O)(CN2N=CN=C2)C=2C(=CC(F)=CC=2)F)=NC=NC=C1F BCEHBSKCWLPMDN-MGPLVRAMSA-N 0.000 description 1
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- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
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- 239000011701 zinc Chemical class 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D307/84—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D307/85—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
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- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/30—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the groups —CO—N< and, both being directly attached by their carbon atoms to the same carbon skeleton, e.g. H2N—NH—CO—C6H4—COOCH3; Thio-analogues thereof
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- A—HUMAN NECESSITIES
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- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
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- A—HUMAN NECESSITIES
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- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/04—Sulfonic acids; Derivatives thereof
- A01N41/06—Sulfonic acid amides
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- A—HUMAN NECESSITIES
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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- A—HUMAN NECESSITIES
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
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- A—HUMAN NECESSITIES
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/12—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings condensed with a carbocyclic ring
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- A—HUMAN NECESSITIES
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- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
- A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
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- A—HUMAN NECESSITIES
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- 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
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
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- A—HUMAN NECESSITIES
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- 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
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Description
201136518 六、發明說明: 【發明所屬之技術領域j 本發明係有關一種新穎之農藥、其製法及其作為活性 成份之用途,尤其作為殺昆蟲劑及殺壁蝨劑之用途。 【先前技術】 文獻中已說明特定之肉桂醯胺及其作為醫藥之用途, 參見例如:WO-A-2002/096858。已驚人地發現,特定之醯 胺類(尤指經i烧基取代之醯胺類)具有強力殺昆蟲及殺壁 蟲性質’同時具有良好之植物耐受性、對恆溫動物具有有 利之毒性及良好之環境相容性。然而,WO-A-2002/096858 中並未揭示本發明之新穎化合物。 【發明内容】 因此,本發明提供一種通式⑴化合物,
其中
Rl為氫、鹵素、硝基、氰基、可視需要經單取代或經相同 或相異取代基多取代之Ci-CV烷基、CVCV烯基、C2_C6_ 块基、燒氧基、Ci_C6·燒基硫基、Ci-C6*·烧基亞石只 酿基、Crc6-貌基磺醯基、(:3-(ν環烷基、C「C6_烧基羰 基、Ci-C6-烷氧基亞胺基-CrC6-烷基、CrCV烷氧基羰 201136518 基、CrC6_烧基胺基羰基、(^-仏二烷基胺基羰基、Ci_c6_ 烧基胺基項醯基、CrCV炫基續醯基胺基、三(crc6-烧 基)矽烷基、芳基、雜芳基、芳基_CrC4_烷基,或雜芳 基-Ci-C4-烧基, 其中該等取代基分別獨立選自:函素、氰基、硝基、羥 基、Ci_C6_烧基、Ci~C6_炫氧基、C^-Cg-環烧基、Ci_C6_ 鹵烧氧基、Cr(V烧基硫基、CKC6-烧基亞續酿基、Ci_c6_ 烷基磺醯基、芳基、雜芳基、芳基烷基或雜芳基烷基, 其中該芳基、雜芳基、芳基烷基、雜芳基燒基取代基可 視需要經以下取代基單取代或經以下相同或相異取代 基多取代:鹵素、氰基、>6肖基、經基、CVC6-烧基、C2-C6-烯基、〇2-(:6_炔基、C3-C6-環烧基、c^-Q-烧氧基、crC6· 鹵烧基、Ci-Cg-鹵烧氧基或C】-C6_统基硫, 或 R為C1-C4碳鍵,其可視需要包含1-2個選自n、S、0所 組成群中之雜原子,其鍵結在兩個相鄰環位置上,且形 成脂系、芳香系、雜芳香系或雜環狀環,其可視需要經 CrCV烧基或鹵素單取代或多取代,此時η為2, η為1、2或3, R為風、氛基、輕基、胺基、可視需要經單取代或經相同 或相異取代基多取代之CrCV烧基、c2-c6-烯基、C2-C6-块基、Ci-Cg-炫*氧基、CrC^-i衣烧基、可視需要經單取 代或經相同或相異取代基多取代之芳基、雜芳基或可視 需要經單取代或經相同或相異取代基多取代之芳基 4 201136518 -CrC6_烷基或雜芳基_Crc4-烷基, 其中該等取代基分別獨立選自:鹵素、氰基、硝基、羥 基、胺基、Ci-CV烧基、C〗-C6-烷氧基、c3-C6-環烷基、 CrQ-鹵烷氧基、CrC6_烷基硫基、胺基、CrC6_烷基胺 基、CrC6_二烷基胺基、CrC4-烷基羰基胺基或crC4-二烷基羰基胺基, 或 R2為可視需要經單取代或多取代之C2-C4-烷基鏈,其中可 穿插0、S或N ’與β形成5-7員環,其可視需要穿插 〇、S或Ν ’且取代基分別獨立選自:鹵素及crC6-烷 基, R3為氫、可視需要經單取代或經相同或相異取代基多取代 之CVCV烷基、C2-C6-烯基、C2-C6-炔基、C3-C6_環烷基、 芳基-CrCV烧基、CrCV烧基Μ基、CVC6-院基續醯基、 芳基羰基、雜芳基羰基、(^-(:6_烷氧基羰基或芳基氧羰 基, 其中該等取代基分別獨立選自:鹵素、氰基、硝基、經 基、C「c6-烧基、Crc6-烧氧基、c3-c6-環燒基、Cl-C6_ 鹵烧氧基、Ci-C0-烧基硫基、芳基、雜芳基、芳基烧基、 雜芳基烷基、CrC4_烷氧基羰基、胺基羰基、Ci_c4_烷 基胺基幾基或CVC4-二烧基胺基羰基, 其中該芳基、雜芳基、芳基烷基、雜芳基烷基取代基可 視需要經以下取代基單取代或經以下相同或相異取代 基多取代:鹵素、氰基、硝基、羥基、crc6-烷基、c2_c6_ 201136518 稀基、c2-c6-炔基、c3<v環烧基、Ci(V烧氧基、Ci々 函烧基、c「c6鹵燒氣基或Ci々燒基硫, V為R4,或 -1貝化学邯仂丞團为诹迸目:_〇_、cH2U__s_、 -N(R ):、-N-CJR )…c(r9)=n_及_c(r9)=c(r1())_,且其 利用單鍵與Q鍵結,其中各例中之第:個(右 置係與Q4連結,其中 R4 要經單取代或經相同或相異取代基 夕1 6元土’其中該等取代基分別獨立選自: 鹵素、CpCV烧基或CrCV^氧基, R8為氫、氰基、絲、可視需要^取代或經相同或相異 取代基多取代之CVCV妓、C2々縣、C2_C6_块基、 cvcv環烧基、Crcv烧氧基、Ci_Q烧基魏基、芳基羰 基、雜芳基幾基、Cr(V烧氧基幾基、芳基燒基或Ci_c4_ 烧基續醯基’ 其中該等取代基分別獨立選自:錢、氰基、墙基、經 基、Ci-CV烷基或CVQ-烷氧基、Ci_c4_烷氧基羰基、 胺基、CrCV烷基胺基、CrCV二烷基胺基、胺基羰基、 CrC6-烷基胺基羰基、CrCr二烷基胺基羰基及芳基 A-CV嫁氧基, R9及R10分別獨立為:氫、鹵素、可視需要經單取代或經 相同或相異取代基多取代之q-cv烷基或crcv環烷 基, 其中該等取代基分別獨立選自:鹵素及Ci-CV*烷基, 6 201136518 R5為氫、鹵素或可視需要經單取代或經相同或相異取代芙 多取代之c^-Cg-烧基或CVC6-院氧基, 其中該等取代基分別獨立選自:鹵素及Ci_C6_境基, R6為氫、鹵素、石肖基、氰基、胺基、經基、可視需要於單 取代或經相同或相異取代基多取代之Ci_e6、燒美、 C2-C6-烯基、C2-C6-块基、C3-C6-環烧基、Ci-Q-燒氧芙、 (Ci-C6·烧氧基)叛基、cvC6-烧基胺基、曱醯基、(c^c 烧基)魏基、Ci-C6_烧氧基亞胺基-C1-C6-燒基、crc _ 烧基胺基、(CVC6-烧基胺基)截基、(CrC:6-二燒基胺美) 幾基、Ci_C6_院基硫基、Ci-C6_院基亞續酿基、c】c 烧基績醯基、CrC6_烧基胺基續醢基、crC6_燒基續酿 基胺基、方基、雜方基、芳基-C1-C4-烧基或雜芳基_Ci〔 烧基, 其中該等取代基分別獨立選自:函素、氰基、硝基、羥 基、胺基、(VCV烧基、(VCV烧氧基、cvc6_環烷基t Ci-Q-南境氧基、Cl_CV烧基硫基、芳基、雜芳基、芳 基烷基或雜芳基烷基, 二 芳基、雜芳基、芳基烧基、雜芳基燒基取代基可 視,要鉍以下取代基單取代或經以下相同或相異取代 $夕取代.卣素、氰基、硝基、羥基、CrC6-烷基、c2-c6- 稀基、c2<v炔基、c3<v環烷基、Ci_c6_烧氧基、Ci_c6_ 函烧基、cvc6-鹵烷氧基或crc6-烷基硫, 或 R為CrC:4噥鏈’其可視需要包含1_2個選自N、s、〇所 201136518 成群中之雜原子,其鍵結在Q4至Q8中兩個相鄰環位 ^上並开^成脂系、芳香系或雜芳香系環,其可視需要
Ci-Cr燒基或鹵素單取代或多取代,此時⑺為2, m 為 〇、1、2、3, χ為crC6-_烷基或C3_C6__環烷基,其可視需要再經單 取代至三取代’其中該等取代基分別獨立選自:羥基、 氰基、Ci-cv烷氧基、Crc4_自烷氧基、(^(^烷氧基羰 基、ci<V·燒基胺基羰基及Ci_C4_二烷基胺基羰基, "W為〇或$, A γ共同為氰基’或為可視需要經單取代或多取代之雜芳 基、雜環基或酮基雜環基, 其中5亥等取代基選自:齒素、硝基、氰基、胺基、羥基, 選自可視需要經單取代或經相同或相異取代基多取代 之胺基、CrC6-烧基、CVCV烧氧基、crc6_烧氧基 _C1-C6-烷基、crC6-烷基羰基、c2_c6_烯基、c2_c6_炔 基、C^CV·環烷基、芳基、雜芳基、Ci_c6_芳基烷基、 Ci-Cp雜芳基烷基、芳基氧、雜芳基氧、磺醯基、Ci_C6_ 烷基硫基、CrC6-烷基亞磺醯基、Ci_C6_烷基磺醯基、 Ci-Cp烷氧基羰基或Crc6-烷基胺基羰基, 其中該等取代基分別獨立選自:鹵素、硝基、氰基、CrC6_ 垸基、CrC6-鹵烷基、Crc6-炫氧基、q-CV鹵烷氧基、 C3-C6-環烷基、C3-C6-環烷基数基、Ci_c6_烧基硫基、 C1-C6·烷基亞磺醯基、crc6-烷基磺醯基、(crC6-烷氧 基)幾基、C2-C6-烯基、c2-c6-炔基、crC6-烧基胺基、 8 201136518 c3-c6-環烷基胺基、(crc6-烷基)c3-c6-環烷基胺基或二 (crc4)烷基胺基, 或 A為二價化學部份基團,其係選自:部份基 團 —NR13C(=0)- 、 -NR13C(=S)- 、 -C(Rn)(R12)NR13C(=0)-、-C(Rn)(U)NR13C(=0)-、 -C(Rn)(R12)N(U)C(=0)- ' -C(Rn)(R12)NR13C(=S)- ' -C(=0)NR13-、-C(=0)NR13CH2-、-C(=S)NR13-、 -C(=S)NR13CH2- 、 -C(=0)NR13C(Rn)=N-0- 、 -C(Rn)=N-0- 、 -C(NH2)=N-0- 、 -C(Rn)=N-0CH2C(=0)NR13- 、 -C(Rn)(R12)NR13C(=0)NR14- 、 -C(Rn)(R12)NR13C(=0)CH2S- 、-NR13(C=0)NR14-、 -C(=0)- 、 -C(=N-0-R13)- 、 -C(=0)0- 、 -C(=0)0CH2C(=0)- 、 -C(=0)0CH2C(=0)NR13-、 -C(=0)NR13CH2C(=0)NR14-、-C(=0)NR13CH2C(=0)-、 -C(=0)NR13CH2C(=0)0-、-C(=0)NR13NR14C(=0)- ' -C(=0)NR13NR14-、-N(R13)-、-C(RU)(R12)NR13-、 -S(=0)p- 、 -S(=0)2NR13- 、 -NR13S(=0)2-、 -C(Rn)(R12)NR13S(=0)2- ' -SO(=N-CN)- ' -S(=N-CN)- > -C(=0)NHS(=0)2-、-C(=0)N(R13)-0- , -C(=0)CH(CN)-或-CH(CN)NR13-,其中該二價化學部份基團之第一個 (左邊)連結位置係結合在環上Q4至Q8中位置之一,且 該第二個(右邊)連結位置結合在Y上,其中 201136518 ^可視需要經取代之W姻,其與環上❼立 置上相鄰碳原子共同形成5·7員環, 氧杳刀別獨立選自:Cl_C3-炫基、CrC3-炫 軋基及函素,且其中 P!之數值可為〇、i或2,及其中
立為氫、氰基、或可視需要經單取代或 基多取代之^4_絲,或CA ^中該等取代基分別獨立選自:鹵素、氰基、確基、羥 基、CVQ-炫基及CrC6^氧基, 或 R 共同為C2-CV燒基或烯基,其形成可視需 要包含1至兩個雙鍵之3-6員環, 或 同為C2 C5_垸基或C3_<:5·烯基’其形成可視需 要包含1至兩個雙鍵之3-7員環, 且其中 R及R /刀別獨立為:氫、可視需要經單取代或經相同或 ,異取代基多取代之Ci_Q•烧基或以·環烧基、 i-C6-烧基躲、CrC6_絲絲基或芳基氧幾基, 其中a亥等取代基分別獨立選自:鹵素、氛基、确基、羥 基、Crcv燒基或Ci_c6•燒氧基, 或 R及R共同為C2_C5_烧基或C3_C5_婦基,其形成可視需 201136518 要包含1至兩個雙鍵之3-7員環, Y為氫、可視需要經單取代或經相同或相異取代基多取代 之C】-C6_烧基、C2-C6_烯基、C2-C6-快基、C3-C6-環烧基、 C3_C6_環烯基、芳基、雜芳基、雜環基或酮基雜環基, 其中該等取代基選自:鹵素、硝基、氰基、羥基,選自 可視需要經單取代或經相同或相異取代基多取代之胺 基、Ci-CV烧基、c2-c6-烯基、c2-c6-炔基、C3-C6-環烧 基、Ci-CV院基魏基、crcv院氧基、crC6-烧氧基幾基、 CrCV烷基硫基、CrCV烷基亞磺醯基、crC6_烷基磺醯 基、CVC6-燒氧基幾基、crc6-烷基胺基幾基、 一烧基胺基裁基、CkCV烧基胺基續醯基、Ci-Q-燒基 磺醯基胺基、芳基、雜芳基、crc6-芳基烷基、CrC6-雜芳基烷基、芳基氧、雜芳基氧或雜環基、Ci_C6_烷氧 基、CrC6_烷基、crC6_烷基羰基、磺醯基、亞磺醯基、 CVCV院基硫或Q-CV燒氧基幾基, 其中該等取代基分別獨立選自:齒素、c]_c6_烷基、經 基、胺基、CVCV烷基羰基、(VQ-齒烷基、crC6-烷氧 基、CrC6-鹵院氧基、C3-C6-環烧基、c3-c6-環烧基幾基、 氰基、硝基、CrC6_烧基硫基、crc6-烷基亞續醯基、 CrC6_烧基磺醯基、(CrCV烷氧基)羰基、c2_c6•烯基、 C2-C6-炔基、Crc6-烧基胺基、C3-C6-環燒基胺基、(Ci_c6_ 烷基)C3_C:6_環烷基胺基、二(C〗-C4)烷基胺基或Ci_c6_ 烷基胺基羰基, Q1至Q3分別獨立為經氫或經R1取代之唆原子,或為N, 201136518 其中該Q1至Q3中之氮原子數不超過2個, Q4為經氫或R6取代或與V鍵結之碳原子,此時v不為 R4,或為N, Q至Q刀別獨立為經虱、r6或A-Y取代之碳原子,或為 Ν’其中該Q4至Q8中之氮原子數不超過2個,其令q5、 Q6、Q7、Q8中僅有一個經Α-γ取代, 及式(I)化合物之鹽類與Ν_氧化物,及其於控制動物害蟲上 之用途。 式(I)化合物若適當時,可呈不同多晶型或不同多晶蜇 之混合物。純多晶型及多晶型混合物二者均形成本發明之 部分標的,且可根據本發明使用。 式(I)化合物包括任何出現之非對映異構物或對映異構 物,及Ε/Ζ異構物。 經取代之丙烯醯胺類係如式(1)之一般術語定義。上式 及下文明確說明之化學式中較佳定義說明於下文中。此等 定義同樣亦適用於式⑴終產物及所有中間物。 式⑴化合物之較佳、更佳及最佳化合物,及使用式(1) 化合物控制害蟲之較佳、更佳及最佳方法中,應考量 R1較佳為氫、函素、确基、氰基、可視需要經單取代或 經相同或相異取代基多取代之Cl_c4-烷基、c2_C6_烯 基、C2-C4-炔基、Crc4_烧氧基、Crc4戈基硫基、CrCV 燒基亞崎酿基、C1-C4-烧基續酿基、c3_c4-環炫基、 CrCr烷基羰基、crC4_烷氧基羰基、Ci_C4_烷基胺基 羰基、CrC4_二烷基胺基羰基或CrC4-烷基胺基磺醯 12 201136518 基, 其中該等取代基分別獨立選自:鹵素、氰基、硝基、 羥基、crc4-烷基、crc4-烷氧基、c3-c4-環烷基、crc4-鹵烧氧基及C1-C4-烧基硫5 η 較佳為1、2或3, R2較佳為氫、氰基、羥基、胺基、可視需要經單取代至 經相同或相異取代基二取代之C1-C4·*炫基、C2_C4_稀 基、c2-c4-炔基、crc4-烷氧基或c3-c6-環烷基, 其中該等取代基分別獨立選自:函素、氰基、硝基、 羥基、胺基、CrCr烷基及Q-C4-烷氧基, R3較佳為氫、可視需要經單取代或經相同或相異取代基 多取代之crc4-烷基、c2-c4-烯基、c2-c4-炔基、c3-c4-環烷基、芳基-crc4-烷基、crc4-烷基羰基、crc4-烷基磺醯基、芳基羰基、雜芳基羰基、Q-C4-烷氧基 罗炭基或芳基氧獄基, 其中該等取代基分別獨立選自:li素、氰基、硝基、 經基、Ci_C6-烧基、Ci_C6_烧氧基、〇3<6-孩烧基、Ci-C6_ 1¾烧氧基、Ci-Cg-院基硫基、C1-C4-烧氧基毅基、胺基 幾·基、C1-C4-烧基胺基幾基及C1-C4-二烧基胺基魏基, V 較佳為R4, 或為二價化學部份基團,其係選自:-0-、-S-、-N(R8)-、 -C(R9)=N-、-N=C(R9)-及-C(R9)=C(R1(})-,且其利用單 鍵與Q4鍵結,其中各例分別於第二個(右邊)連結位置 與Q4連結,其中 13 201136518 R4較佳為氫、鹵素或可視需要經單取代或經相同或相異 取代基多取代之Cl_c4_烷基,其中該等取代基分別獨 立選自:鹵素、CrCr烷基及q-CV烷氧基, R8較佳為氫、氰基、羥基、可視需要經單取代或經相同 或相異取代基多取代之CrCr烷基、C2-C6-烯基、 C2-C6-炔基、crC6-環烧基、CrC4-院氧基、CrC6-炫 氧基幾基、芳基烧基,或CrC4-炫基幾基, 其中該等取代基分別獨立選自:函素、氰基、硝基、 羥基、crc6-烷基、crc6-烷氧基、CrC4-烷氧基羰基、 胺基羰基、crc4-烷基胺基羰基或crc4-二烷基胺基羰 基及芳基-crc4-烷氧基, R9及R10較佳為分別獨立為氫、鹵素或可視需要經單取代 或經相同或相異取代基多取代之CrCr烷基, 其中該等取代基分別獨立選自:鹵素、氰基、及CVCV 烷基, R5較佳為氫、鹵素或可視需要經單取代或經相同或相異 取代基多取代之CrC4-烷基,其中該等取代基分別獨 立選自:鹵素、C1-C4-燒基或C1-C4-烧氧基’ R6較佳為氫、鹵素、硝基、氰基、胺基、羥基、可視需 要經單取代或經相同或相異取代基多取代之Ci-C4_燒 基、C2-C4-烯基、c2-c4-炔基、C3-C5-環烧基、CrC4-烧氧基、(C1-C4-烧氧基)幾基、C〗-C4_炫》基胺基、曱酿 基、(Cl_C4-烷基)羰基、Ci-C4_烷氧基亞胺基-CrC4-烷 基、CrC4-二烷基胺基、(Ci-C4-烷基胺基)羰基、(CrC4- 14 201136518 二烧基胺基)搂基、C1-C4-烧基硫基、C1-C4-烧基亞續 酉藍基、Ci-Czj-烧基續酿基、Ci -C4-烧基胺基續酿基或 Ci-C4_烧基續酿基胺基, 其中該等取代基分別獨立選自:函素、氰基、硝基、 經基、胺基、Ci-Cg-烧基、Ci-Cg-烧氧基、〇3_(^6-壞烧 基、Ci-C6-_烧乳基及Ci-Cg-院基硫’ 或 R6較佳為CrC4碳鏈,其可視需要包含1-2個選自N、S、 0所組成群中之雜原子,其鍵結在Q4至Q8中兩個相 鄰環位置上,且形成脂系、芳香系或雜芳香系環,其 可視需要經CrC6-烷基或鹵素單取代或多取代,此時 m為2, m 較佳為0、1、2、3, X 較佳為CVC4-鹵烷基或c3-c5-鹵環烷基,其可視需要 再經羥基、氰基、或crc4-烷氧基單取代至三取代, W 較佳為Ο或S, A-Y較佳係共同為氰基,或為可視需要經單取代或多取代 之雜環基或酮基雜環基,其選自下列:°比咯基、呤唑 基、異$。坐基、嗔σ坐基、異嗟u坐基、η比吐基、σ米π坐基、 1,2,3-三唑基、1,2,4-三唑基、1,2,3-啐二唑基、1,2,4-口号 二唑基、1,3,4-噚二唑基、1,2,3-噻二唑基、1,2,4-噻二 0坐基、1,3,4-d塞二唾基、四唾基、σ比咬基、σ密咬基、塔 口井基、°比11井基、1,2,4_三11井基、1,3,5-三11井基、°比11各唆 基、異坐咬基、σ比唾π定基、吟唾n定基、嗟峻咬基、 15 τ»米t»生淋基、咪τ»坐咬基、ι,2,4-吟二唾咬基、1,2,4·β塞二 咏0定基、1,2,4-三<»坐咬基、1,3,4·今二α坐β定基、1,3,4-0塞 二。生11定基、1,3,4-三β坐咬基、吼嘻琳基、異β坐琳基、 2.3- 二氫11比唑基、3,4-二氫吡唑基、4,5-二氫吡唑基、 2.3- 二氫坐基、3,4-二氫4唾基、旅《»定基、酮基咐^各 咬基、3-酮基-1,2,4-三哇σ定基、5-酮基_1,2,4-三唾咬基、 >_基吼°各咬基、酮基嗎淋基、_基派咬基及_基娘 4基’ 其中該等取代基選自:齒素、硝基、氰基、胺基、羥 基,選自可視需要經單取代或經相同或相異取代基多 取代之胺基、Ci_C6_燒基、C〗-C6-烧氧基、Ci_C6_烧氧 基-Ci-C6-烧基、CrCV烧基幾基、C2-CV稀基、C2-C6-炔基、C3-C6-環烧基、芳基、雜芳基、CrC6-芳基烧基、 CVC6-雜芳基烷基、芳基氧、雜芳基氧、crc6-烷基硫 基、crc6-烷基亞磺醯基、crc6-烷基磺醯基、crc6-烷氧基羰基及crc6-烷基胺基羰基, 其中該等取代基分別獨立選自:_素、硝基、氰基、 CrCf烧基、CrCf鹵烧基、C]-C6-烧氧基、(^-(:6-鹵 烷氧基、c3_c6-環烷基、C3-C6-環烷基羰基、CrCV烷 基硫基、crc6-烷基亞磺醯基、crc6-烷基磺醯基、 (CrC6-烷氧基)羰基、C2-C6-烯基、c2-c6-炔基、CrC6-烷基胺基、C3-C6-環烷基胺基、(CVC6-烷基)c3-c6-環 烷基胺基或二(crc4)烷基胺基, 或 201136518 A 較佳為二價化學部份基團,其係選自:部份基團 -NR13C(=0)- ' -NR13C(=S)- ' -C(Rn)(R12)NR13C(=0)- ' -C(Ru)(U)NR13C(=0)-、-C(Rn)(R12)NR13C(=S)-、 -C(=0)NR13- 、 -C(=0)N(R13)-0- 、 -c(=o)nr13ch2- -c(=s)nr13_、-c(=s)nr13ch2-、 -C(=0)NR13CH=N-0-、-C(Rn)=N-0-、-C(NH2)=N-0-、 -C(Ru)=N-0CH2C(=0)NR13- 、 -C(Ru)(R12)NR13C(=0)NR14- 、 -C(Rn)- (R12)NR13C(=0)CH2S-、-nr13(c=o)nr14-、-C(=0)-、 -C(=N-0-R13)-、-C(=0)0-、-C(=0)0CH2C(=0)NR13-、 -c(=o)och2c(=o)nh-、-c(=o)nr13ch2c(=o)nr14-、 -C(=0)NR13CH2C(=0)-、-C(=0)NR13CH2C(=0)0-、 C(=0)NR13NR14C(=0)_、-C(=0)NR13NR14·、-N(R13)-、 -C(RU)(R12)NR13- 、-s(=o)p- 、-S(=0)2NR13-、 -NR13S(=0)2- 、 -C(Ru)(R12)NR13S(=0)2- 、 -C(=0)CH(CN)-或-CH(CN)NR13-,其中該二價化學部 份基團之第一個(左邊)連結位置係結合在環上Q4至Q8 中位置之一,且該第二個(右邊)連結位置結合在Y上, 其中 p 較佳之數值可為0、1或2,及其中 U 較佳為可視需要經取代之C2-C4-烷基,其與環上Q4至 Q8位置上的A之連結位置上相鄰碳原子共同形成5-6 員環, 其中該等取代基分別獨立選自:鹵素、CrC3-烷基及 17 201136518
CrCy烷氧基,及其中 R11及R12較佳為分別獨立為氫、氰基、或可視需要經單取 代至經相同或相異取代基三取代之Ci-C4-烧基或 c3-c6-環烷基, 其中該等取代基分別獨立選自:鹵素、氰基、硝基、 羥基、crc6-烷基或crc6-烷氧基, 或 R11及R12共同為C2-C5-烷基或C3-C5-烯基,其形成3-6員 環,其中可視需要包含1至兩個雙鍵, 或 R11及R13共同為C2-C5-烷基或C3-C5-烯基,其形成3-7員 環,其中可視需要包含1至兩個雙鍵, 及其中 R13及R14較佳為分別獨立為氫、可視需要經單取代或經相 同或相異取代基多取代之C1-C4-烧基或匸3-〇6-壞烧 基、crc4_烷基羰基、crc4-烷氧基羰基或芳基氧羰基, 其中該等取代基分別獨立選自:鹵素、氰基、硝基、 輕基、CpC4-炫1基及Ci_C4_烧氧基, 或 R13及R14共同為C2-C5-烷基或C3-C5-烯基,其形成3-7員 環,其中可視需要包含1至兩個雙鍵, Y 較佳為氫或可視需要經單取代或經相同或相異取代基 多取代之C!-C6-烧基、C2-C6-稀基、C2-C6-快基、C3-C6-環烷基、c3-c6-環烯基,為可視需要經單取代或經相 201136518 =相異取代基多取代之苯基或為可視需要經單取代 ^取代之雜環,其係選自:。塞吩基1喃基“比哈 暴、呤唑基、異啐唑基、噻唑基、異噻唑基、吡唑基、 11 米唾基、1,2,3-三唾基、1,2,4-三*基、u,3巧二唾二、 =4,二絲、⑼巧二唾基^嗔一坐基、】^ =Γΐ基、u,4-°塞二吐基、四絲、。比咬基、♦定基、 ;:基…井基、i,2,4-三味基Μ,3〜基省 =土、異咩唑啶基、吡唑啶基、σ号唑啶基、 =咬基、i’3,^二嗤咬基、U,4_噻二唑啶基、i 3 4_ -錢基、料似、異料琳基、2,3_二氫吼哇基、 ,_—心比唑基、4,5_二氫吼唑基、2,3_二氣今唑某、 美3=!:坐基、派咬基、四氣售吩基、派_基、i琳 ^、二馬二琳基、二W南基、四氣娘喃基、四氮嗟吩 戊基、’ 雜環己基、1,3_二氧雜環己基、二氧雜環 氧雜環;ί環戊烯基、四氫咬喃基、二氫咬喃基、 _衣丁基、硫雜環丁基、氧擇基硫 、 =雜環丁基、環氧乙烷基、氮雜環丁、基:氧:雜 IV氮I氮雜環丙烧基、氧氮雜環庚基、氧氮雜環 氣雜環庚基、酮基吡咯啶基、二 基一基料基二基夫 取代基選自:齒素、確基、氰基、經基,選 自叮視㈣經單取代或_同或相異取代基多取代之 201136518 胺基、Crc6-烷基、CrC6-烷氧基、CrC6-烷氧基-(VC6-烷基、Crc6-烷基羰基、C2-C6-烯基、C2-C6-炔基、C3-C6-%烧基、芳基、雜芳基、C1-C6-芳基烧基、C1-C6-雜芳 基烧基、芳基氧、雜芳基氧、C!-C6-烧基硫基、C】-C6-烧基亞續酿基、C1-C6-烧基續酿基、Ci_C6_炫氧基幾基 或雜環基, 其中該等取代基可分別獨立選自:鹵素、硝基、羥基、 胺基、氰基、Ci_C6·烧基、Ci-Cf烧基幾基、Ci-C6-鹵 烷基、crc6-烷氧基、crc6-鹵烷氧基、c3-c6-環烷基、 C3_C6_環烧基截基、C!-C6_烧基硫基、Ci-Cg-烧基亞增 醯基、crc6-烷基磺醯基、(crc6-烷氧基)羰基、c2-c6-烯基、C2-C6-炔基、CVC6-烷基胺基、c3-c6-環烷基胺 基、(CrC6-烷基)C3-C6-環烷基胺基、二(C】-C4)烷基胺 基或crc6-烷基胺基羰基, Q1至Q3較佳為分別獨立為經氫或經R1取代之碳原子’或 為N,其中該Q1至Q3中之氮原子數不超過2, Q4較佳為經氫或R6取代之碳原子,或其係與V鍵結,此 時V不為R4,或為N, Q5至Q8較佳為分別獨立為經氫、R6或A-Y取代之碳原子, 或為N,其中Q4至Q8中之氮原子數不超過2,其中 Q5、Q6、Q7、Q8中僅有一個經A-Y取代, R1更佳為氫、鹵素、硝基、氰基、可視需要經單取代或 經相同或相異取代基多取代之C1-C4-烧基、Ci_C4_炫氧 基、CrCr烷基硫基、CrCr烷基亞磺醯基、CrC4-烷 20 201136518 基磺醯基、CrCr烷基羰基、CrC4_烷氧基羰基、q-Cr 烷基胺基羰基、CrC4-二烷基胺基羰基或crC4-烷基胺 基石黃酸基, η R2 其中該等取代基分別獨立選自:鹵素、氰基、硝基、 輕基、CVQ-烧基、Q-Q-烧氧基、c3-C4-環炫基、CVQ-鹵烷氧基或CrCr烷基硫, 更佳為1、2或3, R3
V R4 R8 乳签搜丞、可視需要經單取代至經相同 或相異取代基三取代之Ci_C4_燒基或CA•烧氧基, =中該等取代齡職域自:㈣、氰基、確基、 2、胺基、crc4·燒基及CKV烧氧基, :氫、可視需要經單取代或經相同或相異取燒基、c2_C4瑪基、c2_c4_ 快基、C1_C4_ 基iii:Cl々烷基磺酿基、Cl々烧氧基或芳 其:該等取代基分別獨立選自 备基、CrC6-烧基、c1<:常亂基A基、 更佳為R4,或為4從基縣, s及-卿8)-,且利用單:〜土團’其係選自:-〇-、 更佳為氮或可視需要=鍵結’其中 三取代之Cl々燒基早:代至經相同或相異取代基 自:i素、Cl-cv燒中讀等取代基分別獨立選 或相異取代基多取代β視需要經單取代或經相同< Ci-c4、燒基、C2_c4_稀基、 2〇ll365l8 C3-C4-;J^基、芳基_crc4-烧基、c「c4-烧氧基、crc6-燒氣基羰基或CrC4-烷基羰基, 其中該等取代基分別獨立選自:li素、氰基、硝基、 經基、Ci-C6-烧基、crC6_烧氧基、C1-C4-烧氧基艘基、 胺基羰基、CrCr烷基胺基羰基、CrC4-二烷基胺基羰 基或芳基-Ci-C4-烧氧基, R 更佳為氫’或可視需要經單取代至經相同或相異取代 基二取代之crcv烧基,其中該等取代基分別獨立選 自·鹵素、C1-C4-烧基或Ci_C4_烧氧基, r6更佳為氫、鹵素、硝基、氰基、可視需要經單取代或 經相同或相異取代基多取代之CrC4_烷基、C2_C4_块 基、CVCr烧氧基、(CrC4-烧基)魏基、((VC4-烧基胺 基)羰基、(CrCV二烷基胺基)羰基、CrCV烷基硫基、 CieC4_烧基亞&酿基、C1-C4-烧基確酿基、C1-C4-烧基 胺基磺醯基或CrCV烷基磺醯基胺基, 其中該等取代基分別獨立選自:鹵素、氰基、端基、 Ci-C^-炫基、Ci-Cg·烧氧基、鹵烧氧基及Ci-Cp 烧基硫, 或 R6 更佳為-och2o-、-ocf2o-、-och2ch2o-、-〇CF2cF2〇· 或·〇Η-CH-CH-CH- ’其中各取代基利用兩個選自q4 至Q8中之相鄰基團形成環, m 更佳為0、卜2、3, X更佳為CrC4_鹵烷基或CrCV鹵環烷基,其可視需要 22 201136518 再經羥基、氰基、或CrC^烷氧基單取代至三取代’ W 更佳為0, A-Y更佳為共同為氰基,或為可視需要經單取代或多取代 之選自下列之雜環基:吡咯基、畤唑基、異崎唑基、 0塞°坐基、異。塞哇基、11比唾基、味β坐基、2-°米吐淋基 . e? 1,2,3-三唑基、ι,2,4-三唑基、1,2,3:二唑基、1,2,4々 二唑基、1,3,4-哼二唑基、1,2,3-嗟二唑基、1,2,4-°塞二 嗤基、1,3,4-喧二嗤基、四嗤基、11比咬基、嘧唆基、0答 0井基、吼啡基、1,2,4-三畊基及1,3,5-三4基, 其中該等取代基選自:函素、硝基、氰基、羥基’選 自可視需要經單取代或經相同或相異取代基多取代之 胺基、CVC4-烷基、CrC4-烷氧基、CrCV烷氧基-CrC4-烷基、C2_C4-炔基、CrC6-烷基硫基、CrC6·烷基亞磺 醯基、q-Q-烷基磺醯基、C3-C6-環烷基、芳基及雜芳 基, 其中該等取代基分別獨立選自:ii素、羥基、胺基、 硝基、氰基、crc6-烷基、crc6-函烷基、crc6·烷氧 基、CrQ-鹵烧氧基、C3-C6-環烧基、C3-C6-環烧基幾 基、Ci-C6-烧基硫基、Ci_C6-烧基亞崎酿基、C!-C6-烧 基磺醯基、(CrC6_烷氧基)羰基、c2-c6-烯基、c2_c6_ 快基、CpC6-院基胺基、C3-CV壞炫*基胺基、(Ci-Cg-烧 基)C3-C6_環烧基胺基、二(C1-C4)炫基胺基或C!-C6-烧 基胺基幾基, A 更佳為二價化學部份基團,其係選自:部份基團 23 201136518 -NR13C(=0)- ' -C(Rn)(R12)NR13C(=0)- ' -C(=0)0- ' -C(Rn)(U)NR13C(=0)-、-C(Rn)(R12)N(U)C(=0)-、 -C(=0)NR13-、-C(=0)N(R13)-0-、-C(=0)NR13CH2-、 -C(=0)NR13CH=N-0- 、 -C(Rn)=N-0- 、 -C(Rn)=N-0CH2C(=0)NR13- 、 -C(Rh)(R12)NR13C(=0)NR14- 、 -C(Rn)(R12)NR13C(=0)CH2S-、-NR13(C=0)NR14-、 -C(=0)-、-C(=N-0-R13)-、_C(=0)NR13CH2C(=0)NR14-、 -C(=0)NR13CH2C(=0)-、-C(=0)NR13CH2C(=0)0-、 -c(=o)nr13nr14c(=o)-、-c(=o)nr13nr14-、-n(r13)-、 -C(Rn)(R12)NR13- 、-S(=0)p- 、-S(=0)2NR13-、 -NR13S(=0)2- 、 -C(Ru)(R12)NR13S(=0)2- 、 C(=0)CH(CN)-或-CH(CN)NR13-,其中該二價化學部份 基團之第一個(左邊)連結位置係結合在環上Q4至Q8 中位置之一,且該第二個(右邊)連結位置結合在Y上, 其中 P 更佳為其數值可為〇、1或2;及其中 U 更佳為可視需要經取代之C2-C4-烷基,其與環上Q4至 Q8位置之A之連結位置上相鄰碳原子共同形成5-6員 環, 其中該等取代基分別獨立選自:CrC3-烷基及鹵素,且 其中 R11及R12更佳為分別獨立為氫、CrC4-烷基或q-Cr鹵烷 基, 24 201136518 或 R11及R12共同為C2-C5-烷基或C3-C5-烯基,其形成3-6員 環,其中可視需要包含1至兩個雙鍵, 或 R11及R13共同為C2-C5-烧基或Q3-C5-稀基’其形成3-7貝 環,其中可視需要包含1至兩個雙鍵, 及其中 R13及R14更佳為分別獨立為氫、可視需要經單取代或經相 同或相異取代基多取代之C1-C4-院基或C3-C6-環燒 基、Q-Q-烷基羰基、芳基氧羰基或Q-Cr烷氧基羰基, 其中該等取代基分別獨立選自:鹵素、氰基、Ci-Cr 烧基及C1-C4-烧氧基, 或 R13及R14共同為C2-C5-烷基或C3-C5-烯基,其形成3-7員 環,其中可視需要包含1至兩個雙鍵, Y 更佳為氫或可視需要經單取代或經相同或相異取代基 多取代之Ci_C6-烧基、C2-C6-婦基、C2-C6-快基、C3-C6-環烷基、c3-c6-環烯基,為可視需要經單取代或經相 同或相異取代基多取代之苯基或為可視需要單取代或 多取代之雜環,其係選自:噻吩基、呋喃基、吡咯基、 σ号唾基、異σ坐基、°塞β坐基、異°塞ϋ坐基、π比唾基、味 唑基、1,2,3-三唑基、1,2,4-三唑基、1,2,3-畤二唑基、 1,2,4-畤二唑基、1,3,4_ 啐二唑基、1,2,3-噻二唑基、1,2,4-°塞二σ坐基、1,3,4-°塞二σ坐基、四β坐基、°比σ定基、嘴咬基、 25 201136518 :吨卜井基必三畊基叫三啡基、。" 基、嗎啉基、四氫哌喃基、1,4’二氧雜環己基 一 己基、二氧雜環戍基、二氧雜環戊烯基、,四: 吱喃基、二氫吱喃基、氧雜環丁基、硫雜環丁基 樓基硫雜環了基、二㈣基硫雜環丁基、環氧乙氧 m、氧氮r :ί、氡氮雜環庚基、氧:雜 環己基、氮雜環庚*、酮基吡咯啶基、二酮基吡 基、酮基嗎似、_錄絲、_絲料及綱基四 氫呋喃基, 其中該等取代基選自:_素、魅、氰基、歸,選 自可視需要經單取代或經相同或相異取代基多取代之 胺基、CrCV烷基、CrCV烷氧基、Ci_C6_烷氧基 烧基、crc6-烧基数基、c2-c6-埽基、C2_C6_块基、C3_C6_ 環烷基、芳基、雜芳基、CrCV芳基烷基、CrC6_雜芳 基烷基、芳基氧、雜芳基氧、Cl_c6_烷基亞磺醯基、 q-c:6-烷基磺醯基、crc:6_烷基硫基、Cl_c6_烷氧基幾 基及雜環基, 其中該等取代基可分別獨立選自:_素、硝基、羥基、 胺基、氰基、Ci-C6-烧基、Ci_C6-烧基叛基、Ci-C6-_ 烷基、CrCV烧氧基、CrC6-_烷氧基、C3-C6-環烷基、 C3-C6-環烧基#炭基、(^-〇6-院基硫基、Ci_CV烧基亞續 醯基、CrC6-烷基磺醯基、(Q-CV烷氧基)幾基、c2-c6-稀基、C2-C6-快基、C〗-C6-烧基胺基、C3T6-環烧基胺 基、(CrC6-烧基)C3-C6-環烧基胺基、二(Ci_C4)烧基胺 26 201136518 基及Cl-C6-烧基胺基幾基’ Q1至Q3更佳為分別獨立為經氫或經R1取代之碳原子,或 為N,其中Q1至Q3中之氮原子數不超過1, Q4更佳為經氫或R6取代之碳原子,或其係與V鍵結,此 時V不為R4,或為N, Q5至Q8更佳為分別獨立為經氫、R6或A-Y取代之碳原子, 或為N,其中該Q4至Q8中之氮原子數不超過1,其中 Q5、Q6、Q7、Q8中僅有一個經A-Y取代, R1最佳為氫、瑣基、氰基、氟、氣、溴、埃、曱基、乙 基、正-或異丙基、氟曱基、氣曱基、三氯甲基、二氟 曱基、二氯氟甲基、氯二氟曱基、三氟曱基、氟乙基、 氯乙基、二氣乙基、二氯乙基、三敗乙基、氯敦乙基、 氯二氟i乙基、二氯氣乙基、四氣乙基、五氣乙基、氣 四氣乙基、三氣乙基、七氣_正丙基、七氟i異丙基、曱 氧基、乙氧基、正-或異丙氧基、氟曱氧基、二氟曱氧 基、三氟曱氧基、曱基硫、乙基硫、二氟曱基硫、三 氟曱基硫、氯二氟曱基硫、曱基亞磺醯基、三氟曱基 亞磺醯基、三氟曱基磺醯基、曱基磺醯基、乙基磺醯 基、乙醯基、丙醯基、甲氧基羰基、乙氧基羰基、曱 基胺基羰基、二曱基胺基羰基或乙基胺基羰基, η 最佳為1、2或3, R2最佳為氫、曱基或乙基, R3最佳為氫、曱基、乙基、2-乙炔基、2-丙烯基、曱氧 基曱基、乙氧基曱基、甲基羰基、乙基羰基、曱氧基 27 201136518 羰基、乙氧基羰基、正丙氧基羰基、異丙氧基羰基、 正丁氧基羰基、第三丁氧基羰基或苯氧基羰基, V 最佳為R4,或為-0-或-N(R8)-,且係利用單鍵與Q4鍵 結,及其中 R4最佳為氫或曱基,及 R8最佳為氫、甲基、乙基、甲基羰基、乙基羰基、曱氧 基曱基、乙氧基曱基、氰基曱基、氰基乙-2-基、丙基、 苯基曱基、丙-2-烯-1-基、丙-2-炔-1-基、苯曱基氧、 曱氧基羰基、乙氧基羰基、曱氧基羰基曱基、乙氧基 幾基曱基、曱氧基徵基乙-2-基、乙氧基幾基乙-2-基、 醯胺基曱基、醯胺基乙基或醯胺基丙-3-基, R5最佳為氫, R6最佳為氫、硝基、氰基、氟、氯、溴、碘 '曱基、乙 基、正或異丙基、正-、異-、第二-或第三-丁基、乙 炔基、丙炔基、氟曱基、氣甲基、三氯曱基、二氟曱 基、二氯氟曱基、氯二氟曱基、三氟曱基、氟乙基、 氣乙基、二氣乙基、二氣乙基、三氟i乙基、氯氟1乙基、 氣二氟乙基、氟二氯乙基、四氟乙基、五氟乙基、氣 四氟乙基、三氯乙基、七氟-正丙基、七氟異丙基、曱 氧基、乙氧基、正-或異丙氧基、氟甲氧基、二氟甲氧 基、三氟曱氧基、曱基硫、乙基硫、二氟曱基硫、三 氟曱基硫、氣二氟曱基硫、曱基亞磺醯基、三氟曱基 亞磺醯基、三氟曱基磺醯基、曱基磺醯基、乙基磺醯 基、乙醯基、丙醯基、曱氧基羰基、乙氧基羰基、曱 28 201136518 基胺基幾基、乙基胺基幾基或二曱基胺基魏基, m 最佳為0、1或2, X 最佳為三氟曱基、二氟曱基、氟曱基、氣二氟曱基、 二氯亂曱基、2-氣乙基、2,2-二氣乙基、2,2,2-三氟 基、1,2,2,2-四氟乙基、1-氯-1,2,2,2-四氟乙基、2-氯-2,2-二鼠乙基、1,1_二鼠乙基、五鼠乙基、七氣-正丙基或 九I-正丁基, W 最佳為0, A-Y最佳為共同為氰基,或為可視需要經單取代或多取代 之選自下列之雜環基:1,2,4-噚二唑-3-基、1H-咪唑-1-基、1H-吼唑-1-基、1H-1,2,4-三唑-1-基、1H-1,2,3-三 唑-1-基、1H-1,3,4-三唑-1-基、1H-1,2,3,4-四唑-1-基或 2H-1,2,3,4-四唑-1-基, 其中該等取代基選自:氟、氯、氰基、羥基、胺基、 曱基、乙基、二氟曱基、三氣甲基、五氟乙基、正-或 異丙基、環丙基、曱氧基、乙氧基、正-或異丙氧基、 氟曱氧基、二氟曱氧基、三氟曱氧基、氟乙氧基、二 氟乙氧基、三氟乙氧基、曱基硫、曱基亞磺醯基、曱 基磺醯基、乙基硫、乙基亞磺醯基、乙基磺醯基、曱 氧基羰基、乙氧基羰基、曱基胺基羰基或二甲基胺基 羰基, 或 A 最佳為二價化學部份基團,其係選自:部份基團 -NR13C(=0)- 、 -C(Rn)(R12)NR13C(=0)- 、 29 201136518 -C(Rn)(R,2)NR13S(=〇)2. 、 -C(=0)NR13- 、 -C(=0)N(R13)-0-、_c(=〇)NR13CH2-、-S(=0)p-、 -S(=0)2NR13_、-C(=0)0_、_c(=〇)NR13CH2C(=0)NR14· -C(Rh)(R12)NR13- 、 c(ru)(u)nr13c(=〇)·及 C(=0)NR13NR14-,其中該二價化學部份基團之第一個 (左邊)連結位置係結合在環上Q4至Q8中位置之一,且 該第二個(右邊)連結位置結合在γ上,其中 U最佳為乙基或正丙基,其與環上Q4至Q8位置之A之 連結位置上相鄰碳原子共同形成5或6員環, p 最佳為0、1、2,及其中 R11及R12最佳為分別為氫或曱基, R13及R14最佳為分別為氫、曱基、乙基、環丙基、氰基乙 基、2-乙炔基、2-丙烯基、甲氧基甲基、乙氧基甲基、 曱基幾基、乙基羰基、正丙基羰基、異丙基羰基、正 丁基羰基、第三-丁基羰基、甲氧基羰基、乙氧基羰基、 正丙氧基幾基、異丙氧基羰基、正丁氧基羰基、第三 丁氧基羰基或苯氧基幾基, γ最佳為氫或可視需要經單取代或經相同或相異取代基 多取代之甲基、乙基、正-或異丙基、正-、異_、第二_ 或第三-丁基、正-、異_、第二-、第三·或新-戊基、環 丙基、環丁基、環戊基、環己基、乙烯基、丙烯基、 丁烯基、戊烯基、乙炔基、丙炔基、丁炔基或戊炔基, 其中至多5個取代基可選自:氟與氣,及至多2個取代 基可選自:溴、氰基、硝基、羥基、胺基、甲基胺基、 201136518 二曱基胺基、環丙基、三氟曱基、曱氧基、乙氧基、 正-或異丙氧基、氟曱氧基、二氟曱氧基、三氟曱氧基、 氟乙氧基、二氟乙氧基、三氟乙氧基、曱基硫、曱基 亞磺醯基、曱基磺醯基、乙基硫、乙基亞磺醯基、乙 基石黃酷基、甲氧基幾基及乙氧基数基, 且其中一個取代基可選自:可視需要經單取代至三取 代之本基、定-2-基、基、°比°定-4-基、 基、11 塞α坐-4-基、吱喃-2-基、σ比唾-1-基、1•比唾-5-基及0比 唑-3-基,其中該等取代基可選自:氟、氯、溴、氰基、 硝基、羥基、曱基、乙基、正-或異丙基、胺基、曱基 胺基、二曱基胺基、環丙基、曱氧基、乙氧基、正-或 異丙氧基、氟曱氧基、二氟曱氧基、三氟曱氧基、氟 乙氧基、二氟乙氧基、三氟乙氧基、曱基硫、曱基亞 磺醯基、曱基磺醯基、乙基硫、乙基亞磺醯基或乙基 磺醯基, 或 為可視需要經單取代至三取代之氧雜環丁-3-基、硫雜 ί哀丁-3-基、1-氧撐基硫雜壤丁-3-基、1,1-二氧撐基硫 雜壤丁-3-基、四氮σ夫喃-2-基、四鼠σ夫喃-3-基、四氮口辰 喃-2-基、四鼠旅喃-3-基、四鼠旅喃-4-基、1,3-二氧雜 環己-2-基、1,3-二氧雜環己-3-基、1,3-二氧雜環己-4-基、1,4-二乳雜J哀己-2-基、嗎°林-1-基、苯基、π比唆 基、atbα定-3-基、°比 β定-4-基、π定-2-基、'^ ^^-4·-基、σ密 σ定-5-基、塔啡-3-基、°比°井-2-基、咬喃-2-基、σ夫喃-3_ 31 201136518 基、噻吩-2_基、噻吩基、吡咯_2•基、噻唑々_基、噻 唑-4-基、噻唾-5-基、丨从嗟工唾_5基、啐唑-2基、 咩哇-4-基、.坐-5_基、異十坐_3_基、異十坐冬基、異 十坐-5-基、1’2,3-今二啥_4•基、u,4巧二唾_2_基、m_ 咪唾_2-基、1H-咪唾冰基、1H“米唾_5_基、ih_d比吐·3_ 基、1HH4-基、1H_ 吼唾 _5_ 基、1h],24_ 三唑-3_ 基、1H-1,2,4_三唾_5_基、1h_12,3_三唾_4 基、脳,2 3· 三唾-5-基、2H-1,2,3-三嗤_2_基、2H-1,2,3-三唾_4_基、 m-w-三唾·2_基、1H-U,3,4_四唾_5_基、2㈤基旅 咬-3-基、2·酮基錢。夫喃·3·基或5,基 其中該取代基可選自 基、胺基、甲基、乙基、二氟甲基、三氟甲基、五氣 乙基、正-或異丙基、環丙基、曱氧基、乙氧基、正· 或異丙氧基、氟甲氧基、二氧基、 氣乙氧基、二氣乙氧基、三氣乙氧基、甲基:氧;基 甲基梅、乙基硫、乙基亞續醯基、乙 ί:甲ί 氧基羰基、乙氧基祕1基胺基幾基 及一f基胺基羰基, Q 1最佳為77卿立為經氫或^Ri取代之碳原子,戋 Q4 tr^rQ、Q3中之氮原子數不超過1, 時V二3 R取代之碳原子’或其係與V鍵結,此 Q5^::7/〇ir'R6"A-y"^^- ^ Q至Q 1(7之氫原子數不超過1,且其令 32 201136518 Q5、Q6、Q7、Q8中僅有一個經Α_γ取代。 上述取代基R1至R6、X、w、A、Υ及Q1至Q8之一 般、較佳、更佳及最佳定義可依據本發明之需要相互組合。 較佳之本發明化合物為新穎之式(IA)至(ID)化合物
33 201136518
(ID-1) Α-Υ
其中 (R1)。、R3、R8、(R6)m、χ、Α及 Y(亦即 A、Y及 A-Y)代表 上述一般較佳、更佳及最佳定義。 同樣較佳之本發明化合物為表1至7所示之通式(la)、 (lb)、(Ic)、(Id)、(Ie)、(If)及(Ig)化合物,且尤指表 1 至 7 所示之明確化合物。 本通式(I)化合物可視需要具有對掌性碳原子。 依據Cahn,Ingold及Prelog (CIP規則),此等取代基可 能呈(R)或(S)組態。 本發明包括通式(I)化合物在特定對掌性碳原子上出現 之(S)及(R)組態’此表示本發明涵蓋之通式⑴化合物中,該 碳原子分別獨立呈 ⑴(R)組態;或 (2) (S)組態。 若通式⑴或式(IA)至(ID)化合物具有許多個對掌性中 心時,則可能出現該對掌性中心之組態之所需組合,此表 示 (1) 其中一個對掌性中心可能呈(R)組態,及另一個對掌性 中心呈(S)組態; (2) 其中一個對掌性中心可能呈(R)組態’及另一個對掌性 34 201136518 中心呈(R)組態;及 及另一個對掌性 (3)其中一個對掌性中心可能呈(s)組態, 中心呈(S)組態。 式(I)化合物同樣包括任何出現之非對映異構 異構物’ A E/Z異構物’及式⑴化合物之鹽類與N_氣化物: 及其於控制動物害蟲上之用途。 本發明亦有關-種以本發明通式(1)化合物於製造農藥 上之用途。 ' 本發明亦有關一種農藥,其包含本發明通式⑴化合物 及/或其鹽類,其含量為占農藥重量> 〇 〇〇〇〇〇〇〇1重量%, 較佳>0.001重量%至95重量%之生物活性量。 本發明亦有關一種控制動物害蟲之方法,其中使本發 明通式(I)化合物作用在動物害蟲及/或其棲息地上。 本發明活性成份可提供良好之植物耐受性、對恆溫動 物有利之毒性及良好之環境相容性,適合保護植物與植物 器官’提高收成產量,改善收成材料之品質及控制動物害 蟲,尤指出現在農業、園藝、動物飼養、森林、花園與休 間設施、保護庫存產品與原料,及在衛生等方面之動物害 蟲,尤指昆蟲、蜘蛛類、蠕蟲、線蟲與軟體動物。其較適 用為作物保護劑。其可活性對抗一般敏感性與抗性品種, 及對抗所有或某些發展階段。上述害蟲包括: 毛兹目(Phthiraptera),例如:毛兹屬(Damaliniaspp.)、 豬兹屬(Haematopinus spp.)、犬兹屬(Linognathus spp.)、人 蝨屬(Pediculus spp.)、獸鳥兹屬(Trichodectes spp.)。 35 201136518 物形綱(Arachnida),例如:粗腳粉瞒(Acarus spp.)、桂 瘤節碑(Aceria sheldoni)、刺皮癭蜗屬(Aculops spp.)、刺疼 蜗属(Aculus spp.)、花蜱屬(Amblyomma spp.)、 橫紋葉瞒 (Amphitetranychus viennensis)、銳緣碑屬(Argas spp.)、牛蜱 屬(Boophilus spp.)、紅鬚蜗屬(Brevipalpus spp.)、苜蓿苔蜗 (Bryobia praetiosa)、恙蜗屬(Chorioptes spp.)、 雞皮刺蟎 (Dermanyssus gallinae)、始葉蜗屬(Eotetranychus spp.)、梨 上癌蜗(Epitrimerus pyri)、真葉蜗屬(Eutetranychus spp.)、 瘤蟎屬(Eriophyes spp·)、足海鐮螯蟎(Halotydeus destructor)、半跗線蜗屬(Hemitarsonemus spp.)、璃眼蜱屬 (Hyalomma spp.)、硬蜱屬(Ixodes spp.)、黑寡婦球腹蛛 (Latrodectus mactans)、後紅葉蜗屬(Metatetranychus spp.)、 Nuphersa屬、小爪蜗屬(Oligonychus spp·)、鈍緣蜱屬 (Ornithodoros spp.)、紅Ji知蛛屬(Panonychus spp.)、橘錄瞒 (Phyllocoptruta oleivora)、雜食線瞒屬(Polyphagotarsonemus latus)、癢瞒屬(Psoroptes spp.)、扇頭碑屬(Rhipicephalus spp.)、根蜗屬(Rhizoglyphus spp.)、人療蟎屬(Sarcoptes spp.)、蛾(Scorpio maurus)、狹咐線蜗屬(Stenotarsonemus spp.)、細蜗屬(Tarsonemus spp.)、紅葉瞒屬(Tetranychus spp.)、刺皮癭蜗(Vasates lycopersici)。 雙殼綱(Bivalva),例如:飾貝屬(Dreissena spp.)。 唇足目(Chilopoda),例如:地埃虫公屬(Geophilus spp.) 與姑挺屬(Scutigera spp.)。 鞘翅目(Coleoptera),例如:鑲邊黃瓜曱蟲(Acalymma 36 201136518 vittatum)、大豆象(Acanthoscelides obtectus)、麗金龜屬 (Adoretus spp.)、赤揚紫跳曱(Agelastica alni)、叩頭蟲屬 (Agriotes spp.)、六月金龜子(Amphimallon solstitialis)、食 骸蟲(Anobium punctatum)、天牛屬(Anoplophora spp.)、棉 鈴象鼻蟲(Anthonomus spp.)、蠢屬(Anthrenus spp·)、梨象屬 (Apion spp.)、甘蔗金龜屬(Apogonia spp.)、隱食曱屬 (Atomaria spp·)、小鰹節蟲屬(Attagenus spp.)、豆象 (Bruchidius obtectus)、豆象曱屬(Bruchus spp.)、金花蟲屬 (Cassida spp·)、大豆葉曱(Cerotoma trifurcate)、象鼻蟲屬 (Ceuthorrhynchus spp.)、小金花蟲屬(Chaetocnema spp.)、牛 蒡象曱(Cleonus mendicus)、金針蟲屬(Conoderus spp.)、球 莖象鼻蟲屬(Cosmopolites spp·)、蜻螬(Costelytra zealandica)、Ctenicera 屬、象甲屬(Curculio spp.)、柳小隱 0彖象曱(Cryptorhynchus lapathi)、莖象鼻蟲(Cylindrocopturus SPP.)、皮蠹屬(Dermestes spp.)、葉曱屬(Diabrotica spp.)、 姓填屬(Dichocrocis spp·)、Diloboderus 屬、瓢蟲屬(Epilachna spp.)、跳曱屬(Epitrix spp·)、煙草鑽孔蟲(Faustinus cubae)、 麥蛛曱(Gibbium psylloides)、菜心填(Hellula undalis)、白績 if (Heteronychus arator)、天牛屬(Heteronyx spp.)、 Hylamorpha elegans、象天牛(Hylotrupes bajulus)、苜蓿象鼻 蟲(Hypera postica)、小蠢屬(Hypothenemus spp.)、總角金龜 (Lachnosterna consanguinea)、負泥曱屬(Lema spp.)、馬鈐 薯甲蟲(Leptinotarsa decemlineata)、潛葉蛾屬(Leucoptera SPP.)、稻象曱(Lissorhoptrus oryzophilus)、黃象曱屬(Lixus 37 201136518 spp.)、葉曱屬(Luperodes spp.)、粉蠹屬(Lyctus spp.)、 Megascelis 屬、叩頭蟲(Melanotus spp.)、花粉曱(Meligethes aeneus)、吹粉金龜(Melolontha spp.)、天牛屬(Migdolus spp.)、天牛屬(Monochamus spp.) 、 Naupactus xanthographus、金黃蛛曱(Niptus hololeucus)、犀角金龜 (Oryctes rhinoceros)、鑛胸粉扁蟲(Oryzaephilus surinamensis)、稻象鼻蟲(Oryzaphagus oryzae)、深溝象曱 (〇1丨00*1^11(:11113 5卩卩.)、銀點花金龜(0\)^61〇11丨&』11(;1111〇1&)、猿 葉蟲(Phaedon cochleariae)、食葉蟲屬(Phyllophaga spp.)、 葉蚤屬(Phyllotreta spp.)、曰本麗金龜(Popillia japonica)、 Premnotrypes 屬、油菜蘭跳曱(Psylliodes spp.) ' 蛛曱屬 (Ptinus spp.)、黑根瓢蟲(Rhizobius ventralis)、粉長螽蟲 (Rhizopertha dominica)、米象屬(Sitophilus spp.)、穀象屬 (Sphenophorus spp·)、莖象屬(Sternechus spp.)、爲肩象屬 (Symphyletes spp·)、象鼻蟲屬(Tanymecus spp.)、粉曱 (Tenebrio molitor)、擬縠盜屬(Tribolium spp.)、鰹節蟲屬 (Trogoderma spp.)、象曱屬(Tychius spp.)、虎天牛屬 (Xylotrechus spp.)、步曱屬(Zabrus spp.)。 彈尾目(Collembola),例如:棘跳蟲(Onychiurus armatus)。 重足目(Diplopoda),例如:Blaniulus guttulatus。 雙翅目(Diptera),例如:伊蚊屬(Aedes spp.)、潛绳屬 (Agromyza spp.)、按實繩屬(Anastrepha spp.)、按蚊屬 (Anopheles spp.)、,癭蚊屬(Asphondylia spp.)、實繩屬 38 201136518 (Bactrocera spp.)、毛蚊(Bibio hortulanus)、麗蠅(Calliphora erythrocephala)、地中海果實蠅(Ceratitis capitata)、搖蚊屬 (Chironomus spp.)、金繩屬(Chrysomyia spp.)、刺蚊屬 (Cochliomyia spp·)、康癭蚊屬(Contarinia spp.)、糞蠅 (Cordylobia anthropophaga)、庫蚊屬(Culex spp·)、疽蠅屬 (Cuterebra spp.)、果蝇(Dacus oleae)、癭蚊屬(Dasyneura spp.)、地種繩屬(Delia spp.)、人膚4^(Dermatobia hominis)、 獲獲繩(Drosophila spp.)、象鼻轰屬(Echinocnemus spp.)、廢 繩屬(Fannia spp.)、胃繩屬(Gastrophilus spp.)、稻心繩 (Hydrellia spp.)、種繩屬(Hylemyia spp.)、Hyppobosca 屬、 皮繩屬(Hypoderma spp.)、潛繩屬(Liriomyza spp·)、綠頌屬 (Lucilia spp.)、家繩屬(Musca spp.)、綠墙屬(Nezara spp.)、 狂蜗屬(Oestrus spp.)、瑞典繩(Oscinella frit)、潛葉蛾屬 (Pegomyia spp.)、蚤繩屬(Phorbia spp.)、癭蚋屬(Prodiplosis spp.)、胡蘿蔔繩(Psila rosae)、果實繩屬(Rhagoletis spp.)、 螫题屬(Stomoxys spp.)、it屬(Tabanus spp.)、Tannia 屬、直 斑繩屬(Tetanops spp.)、大蚊屬(Tipula spp.)。 腹足綱(Gastropoda),例如:域輸屬(Arion spp.)、紅扁 蜂屬(Biomphalaria spp.)、泡螺屬(Bulinus spp.)、灰始输屬 (Deroceras spp.)、土 堝螺屬(Galba spp.)、椎實螺屬(Lymnaea spp.)、釘螺屬(Oncomelania spp.)、福壽螺屬(Pomacea spp.)、 琥珀螺屬(Succinea spp·)。 螺蟲類,例如:十二指腸鉤蟲(Ancylostoma duodenale)、鉤蟲(Ancylostoma ceylanicum)、描鉤蟲 39 201136518 (Acylostoma braziliensis)、鉤蟲屬(Ancylostoma spp.)、人虫回 轰(Ascaris lubricoides)、虫回蟲屬(Ascaris spp.)、布魯線蟲 (Brugia malayi、Brugia timori)、仰口 線蟲屬(Bunostomum spp.)、腸線蟲屬(Chabertia spp.)、支澤吸蟲屬(Clonorchis spp.)、古柏蟲屬(Cooperiaspp.)、雙腔吸蟲屬(Dicrocoelium spp.)、網尾線蟲(Dictyocaulus filaria)、闊節二葉槽蟲 (Diphyllobothrium latum)、地中海龍線蟲(Dracunculus medinensis)、棘球、縧蟲(Echinococcus granulosus)、球縧蟲 (Echinococcus multilocularis) 、 虫堯蟲 (Enterobius vermicularis)、吸蟲屬(Faciola spp. )、血矛線蟲屬 (Haemonchus spp.)、異刺線蟲屬(Heterakis spp.)、微小膜殼 斜条蟲(Hymenolepis nana)、下圓線蟲屬(Hyostrongulus spp.)、羅阿 jk 絲蟲(Loa Loa)、細頸線蟲屬(Nematodirus spp.)、結線蟲屬(Oesophagostomum spp.)、後睪吸蟲屬 (Opisthorchis spp.)、盤尾線蟲(Onchocerca volvulus)、胃絲 蟲屬(Ostertagia spp.)、並殖吸蟲屬(Paragonimus spp·)、裂吸 轰屬(Schistosomen spp.)、糞類圓線蟲(Strongyloides fuelleborni、Strongyloides stercoralis)、糞類圓線蟲屬 (Strongyloides spp.)、帶 If条蟲(Taenia saginata、Taenia solium)、旋毛線:&(Trichinella spiralis、Trichinellanativa、 Trichinella britovi 、 Trichinella nelsoni 、 Trichinella pseudopsiralis)、毛圓線蟲屬(Trichostrongulus spp.)、鞭蟲 (Trichuris trichuria)、吳策線蟲(Wuchereria bancrofti)。 亦可控制原蟲,如:艾美球蟲(Eimeria)。 201136518 異翅目(Heteroptera),例如:南瓜緣蝽(Anasatristis)、 芒果墙屬(Antestiopsisspp.)、麥長墙屬(Blissusspp.)、盲蝽 屬(Calocoris spp·)、盲蝽(Campylomma livida)、二尾辑屬 (Cavelerius spp.)、臭蟲屬(Cimex spp.)、(Collaria spp.)、盲 蝽(Creontiades dilutus)、胡椒緣墙(Dasynus piperis)、二葉 嗓蝽(Dichelops furcatus)、Diconocoris hewetti、蜂象屬 (Dysdercus spp.)、臭蝽屬(Euschistus spp.)、刺堵屬 (Eurygaster spp.)、夜蛾屬(Heliopeltis spp.)、Horcias nobilellus、緒緣蝽屬(Leptocorisa spp.)、葉足緣蝽 (Leptoglossus phyllopus)、盲蝽屬(Lygus spp.)、蔗黑長蝽 (Macropes excavatus)、盲墙(Miridae)、Monalonion atratum、 綠蝽屬(Nezara spp.)、盾培屬(Oebalus spp.)、培科 (Pentomidae)、擬配軍蟲(Piesma quadrata)、壁培屬 (Piezodorus spp.)、紅盲蝽(Psallus seriatus)、Pseudacysta persea、紅腹獵墙屬(Rhodnius spp.)、可可褐盲培 (Sahlbergella singularis) ' 土培(Scaptocoris castanea)、稻黑 蜂屬(Scotinophora spp.)、梨花網培(Stephanitis nashi)、 Tibraca 屬、椎培屬(Triatoma spp.)。 同翅目(Homoptera) ’例如:無網長管财屬(Acyrthosipon spp.)、Acrogonia 屬、飛風屬(Aeneolamia spp.)、木虱屬 (Agonoscena spp.)、粉風屬(Aleurodes spp·)、甘蔗粉虱 (Aleurolobus barodensis)、粉風屬(Aleurothrixus spp.)、小綠 葉蟬屬(Amrasca spp.)、圓尾财(Anuraphis cardui)、圓纷屬 (八0111(^11&5卩卩.)、蘇聯黃粉辑(八卩11&1105^吕111&卩^4)、財蟲屬 201136518 (Aphis spp.)、葡萄浮塵子(Arboridia apicalis)、小圓盾介殼 蟲屬(Aspidiella spp.)、圓虫介屬(Aspidiotus spp.)、Atanus 屬、 茄溝無網财(Aulacorthum solani)、粉風屬(Bemisia spp.)、桃 短尾财(Brachycaudus helichrysii)、微管财屬(Brachycolus spp.)、甘藍财(Brevicoryne brassicae)、葉曱(Calligypona 1113巧0^&)、黃頭大葉蟬(匸&1:1^006卩1131&£'111§丨(13)、甘蔗棉辑 (Ceratovacuna lanigera)、沫蟬科(Cercopidae)、堪紛屬 (Ceroplastes spp.)、草每毛管财(Chaetosiphon fragaefolii)、 蔬黃雪盾蛉(Chionaspis tegalensis)、葉蟬(Chlorita onukii)、 核桃黑斑财(Chromaphis juglandicola)、茶褐圓蛉 (Chrysomphalus ficus)、葉蟬(Cicadulina mbila)、 Coccomytilus halli、軟紛屬(Coccus spp.)、茶蔗隱瘤額財 (Cryptomyzus ribis)、葉蟬(Dalbulus spp.)、粉虱屬 (Dialeurodes spp.)、木II屬(Diaphorina spp.)、盾紛屬(Diaspis spp.)、棉虫介屬(Drosicha spp.)、圓尾财屬(Dysaphis spp.)、粉 矫屬(Dysmicoccus spp.)、微葉輝屬(Empoasca spp.)、棉辑 屬(Eriosoma spp.)、斑葉蟬屬(Erythroneura spp.)、二葉蟬 (Euscelis bilobatus)、粉介殼蟲屬(Ferrisia spp.)、咖啡根蛉 (Geococcus coffeae)、嚴壇屬(Hieroglyphus spp.)、玻璃葉蟬 (Homalodisca coagulate)、桃吹粉坊(Hyalopterus arundinis)、絲紛屬(Icerya spp.)、葉禪屬(Idiocerus spp.)、 葉蟬屬(Idioscopus spp.)、稻灰飛風(Laodelphax striatellus)、蠛输屬(Lecanium spp.)、蠣紛屬(Lepidosaphes SPP.)、菜溢管財(Lipaphiserysimi)、長鬚財屬(Macrosiphum 42 201136518 spp·)、沐蟬屬(Mahanarva spp.)、暗圓纷(Melanaphis sacchari)、Metcalfiella 屬、薔薇麥财(Metopolophium 出1*110(111111)、黑緣平翅斑蚜(]^〇1^11丨&(1(^&1丨3)、]\4〇1^11丨〇?515 pecanis、桃蚜屬(Myzus spp.)、茼蒿蚜(Nasonovia ribisnigri)、葉蟬(Nephotettix spp.)、褐飛虱(Nilaparvata lugens)、Oncometopia 屬、牲蚧(〇rthezia praelonga)、楊柳 粉風(Parabemisia myricae)、木風屬(Paratrioza spp.)、盾虫介 屬(Parlatoria spp.)、癭棉辑屬(Pemphigus spp.)、玉米飛II (Peregrinus maidis)、粉虱屬(Phenacoccus spp.)、揚平翅棉 蚜(Phloeomyzus passerinii)、瘤蚜(Phorodon humuli)、桃根 蚜屬(Phylloxera spp.)、橘長盾蚧(Phmaspis aspidistrae)、粉 蚧屬(Planococcus spp.)、梨形原棉蚧(protopuivinaria 卩丫1^0171^)、桑白蚧(?3611(13111&。33卩15?61113§01^)、粉介殼蟲 (Pseudococcus spp.) ' 木虱蟲(Psylla spp.)、金小蜂屬 (Pteromalus spp.)、飛虱屬(Pyrilla spp.)、圓纷屬 (Quadraspidiotus spp.)、Quesada gigas、粉介殼蟲屬 (Rastrococcus spp.)、頸狀蚜屬(Rhopalosiphum spp.)、扁介 殼蟲屬(Saissetia spp.)、螻姑(Scaphoides titanus)、麥二叉财 (Schizaphis graminum)、盾介殼蟲(Selenaspidus articulatus)、飛虱屬(Sogata spp.)、白背飛虱(s〇gatella furcifera)、飛虱屬(Sogatodes spp·)、沫蟬(stictocephala festina)、Tenalaphara malayensis、核桃黑蚜(Tinocallis caryaefoliae)、沫蟬屬(Tomaspis spp.)、二又蚜屬(T〇XOptera spp·)、桑粉蝨(Trialeurodes spp.)、木虱屬(Tri〇za Spp.)、小 43 201136518 葉蟬屬(Typhlocyba spp.)、盾蛉屬(Unaspis spp.)、葡萄根瘤 財(Viteus vitifolii)、葉蟬屬(Zygina spp.)。 膜翅目(Hymenoptera),例如:葉蜂屬(Athalia spp.)、 松葉蜂屬(Diprion spp.)、葉蜂屬(Hoplocampa spp.)、蠘屬 (Lasius spp.)、磨蟻(Monomorium pharaonis)、胡蜂屬(Vespa spp.)。 等足目(Isopoda),例如:鼠婦(Armadillidium vulgare)、 海组(Oniscus asellus)、球鼠婦(Porcellio scaber)。 等翅目(Isoptera),例如:切葉蟻屬(Acromyrmex spp.)、 螞蟻(Atta spp.)、白蟻(Cornitermes cumulans、Microtermes obesi)、土 白蟻屬(Odontotermes spp.)、白蟻屬(Reticulitermes spp.)。 鱗翅目(Lepidoptera),例如:梁劍紋夜蛾(Acronicta major)、捲葉蛾屬(Adoxophyes spp.)、電紋夜蛾(Aedia leucomelas)、地老虎屬(Agrotis spp.)、棉葉波紋夜蛾 (Alabama spp.)、蘋果蠹蛾(Amyelois transitella)、條麥蛾屬 (Anarsia spp.)、夜蛾屬(Anticarsia spp.)、黃煩屬(Argyroploce spp.)、甘藍夜蛾(Barathra brassicae)、單帶弄蝶(Borbo cinnara)、棉葉穿孔潛蛾(Bucculatrix thurberiella)、松尺虫筻 (Bupalus piniarius)、夜蛾屬(Busseola spp.)、捲葉蛾(Cacoecia spp.)、茶细蛾(Caloptilia theivora)、煙捲葉蛾(Capua reticulana)、蘋果蠹蛾(Carpocapsa pomonella)、桃姓果蛾 (Carposina niponensis)、冬尺蛾(Cheimatobia brumata) ' 填 屬(Chilospp.)、雲杉捲葉蛾(Choristoneuraspp.)、葡萄果蠹 201136518 蛾(Clysia ambiguella)、捲模屬(Cnaphalocerus spp.)、 Cnephasia spp.、細蛾屬(Conopomorpha spp.)、黑象甲屬 (Conotrachelus spp.)、Copitarsia 屬、小卷蛾屬(Cydia spp.)、 夜蛾(Dalaca noctuides)、野填屬(Diaphania spp.)、小蔗煩 (Diatraea saccharalis)、埃及金剛鑽(Earias spp.)、柑橘果蛾 (Ecdytolopha aurantium)、南美玉米苗斑模(Elasmopalpus lignosellus)、非洲莖模(Eldana saccharina)、粉填(Ephestia kuehniella)、小卷蛾屬(Epinotia spp.)、蘋果飛蛾(Epiphyas postvittana)、模蛾屬(Etiella spp.)、Eulia 屬、環針單紋卷蛾 (Eupoecilia ambiguella)、毒蛾(Euproctis spp.)、切根蟲屬 (Euxoa spp.)、褐夜蛾屬(Feltia spp.)、大躐煩(Galleria mellonella)、Gracillaria 屬、小食心蟲屬(Grapholitha spp.)、 镇蛾屬(Hedylepta spp·)、夜蛾屬(Helicoverpa spp.)、棉鈐蟲 屬(Heliothis spp.)、褐織夜蛾(Hofmannophila pseudospretella)、斑填屬(Homoeosoma spp.)、捲葉蛾 (Homona spp.)、櫻桃巢蛾(Hyponomeuta padella)、柿食心蟲 (Kakivoria flavofasciata)、黏蟲屬(Laphygma spp.)、果蠹蛾 (Laspeyresia molesta)、蘇黃斑模(Leucinodes orbonalis)、 潛葉蛾屬(Leucoptera spp.)、細蛾屬(Lithocolletis spp.)、綠 果夜蛾(Lithophane antennata)、捲蛾屬(Lobesia spp.)、豆 白緣切根蟲(Loxagrotis albicosta)、毒蛾屬(Lymantria 叩卩-)、萊氏蛾(1^01^1&5卩卩.)、金龜(1^&1&(:030111&1161^1^)、 莖夜蛾屬(Mocisspp.)、東方黏蟲(Mythimnaseparate)、水堪 45 201136518 屬(Nymphula spp.)、Oiketicus spp.、夜蛾屬(Oria spp.)、镇 蛾(Orthaga spp.)、玉米模屬(Ostrinia spp.)、稻負泥蟲 (Oulema oryzae)、小眼夜蛾(Panolis flammea)、弄蝶屬 (Parnara spp,)、紅鈐蟲(Pectinophora spp.)、潛葉蛾屬 (Perileucoptera spp.)、蠹蛾屬(Phthorimaea spp.)、橘葉潛蛾 (Phyllocnistis citrella)、细蛾屬(Phyllonorycter spp.)、粉蝶 屬(Pieris spp.)、荷蘭石竹小卷蛾(Platynota stultana)、擬尺 ^(Plusia spp.)、小菜蛾(Plutella xylostella)、巢蛾屬(Prays spp.)、黏蟲屬(Prodenia spp.)、天蛾屬(Protoparce spp.)、黏 蟲屬(Pseudaletia spp.)、大豆夜蛾(Pseudoplusia includens)、 野填(Pyrausta nubilalis)、薄荷灰夜蛾(Rachiplusia nu)、三 化填屬(Schoenobius spp.)、白禾填蛾屬(Scirpophaga spp.)、 黄地老虎(Scotia segetum)、虹莖夜蛾屬(Sesamia spp.)、捲 葉蛾屬(Sparganothis spp.)、黏蟲屬(Spodoptera spp.)、舉肢 蛾屬(Stathmopoda spp.)、潛葉轰(Stomopteryx subsecivella)、透翅蛾屬(Synanthedon spp.)、馬鈐薯塊莖蛾 (Tecia solanivora)、Thermesia gemmatalis、網衣蛾(Tinea pellionella)、袋衣蛾(Tineola bisselliella)、櫟綠捲葉蛾 (Tortrix spp.)、夜蛾屬(Trichoplusia spp.)、番祐斑潛繩(Tuta absoluta)、小灰蝶屬(Virachola spp.)。 直翅目(Orthoptera),例如:家蟪蟀(Acheta domesticus)、東方蜚嫌(Blatta orientalis)、德國蜚蠊(Blattella germanica)、草猛(Dichroplus spp.)、螻姑(Gryllotalpa spp.)、 馬得拉蜚嫌(Leucophaea maderae)、飛 *皇屬(Locusta spp.)、 46 201136518 負虫皇屬(Melanoplus spp.)、美洲大蠊(Periplaneta 蚤目(Siphonaptera),例如:|苗蚤屬(Ceratophyllus spp·)、印度鼠蚤(Xenopsylla cheopis)。 結合目(Symphyla),例如:么姑屬(Scutigerella spp.)。 纓翅目(Thysanoptera),例如:黃呆薊馬(Anaphothrips obscurus)、稻薊馬(Baliothrips biformis)、Drepanothris reuteri、Enneothrips flavens、薊馬屬(Frankliniella spp.)、薊 馬屬(Heliothrips spp.)、桃薊馬(Hercinothrips femoralis)、大 花薊馬(Rhipiphorothrips cruentatus)、黃薊馬屬(Scirtothrips spp.)、薊馬(Taeniothrips cardamoni)、薊馬屬(Thrips spp.)。 總尾目(Thysanura),例如:西洋衣魚(Lepisma saccharina) ° 植物寄生性線蟲包括,例如:葉芽線蟲屬 (Aphelenchoides spp.)、黏液囊線蟲屬(Bursaphelenchus spp.)、包囊線蟲(Ditylenchusspp.)、包囊線蟲屬(Globodera spp·)、異皮線蟲屬(Heterodera spp.)、長針線蟲屬(Longidorus spp.)、根瘤線蟲屬(Meloidogyne spp.)、根腐線蟲屬 (Pratylenchus spp.)、穿孔線蟲(Radopholus similis)、鬃根線 蟲屬(Trichodorus spp.)、墊刀線蟲(Tylenchulus semipenetrans)、劍線轰屬(Xiphinema spp.)。 若適當時,式(I)化合物亦可在某些濃度或施用率下作 為除草劑、安全劑、生長調節劑或改善植物性質之製劑或 作為殺微生物劑使用,例如:殺真菌劑、抗黴劑、殺細菌 47 201136518 劑、殺病毒劑(包括對抗類病毒之製劑)或作為對抗紙 黴襞菌生物體)與RL0(似立克次體生物體)之製劑。若適當 時’其亦可作為合成其他活性祕之中間物或前體。 本發明進一步係有關一種調配物,及由其製成之施用 型式’如:包含至少1本發明活性成份作為 與/或農藥’如:賴水、㈣水及喷。該施用型式可 進-步包含作物保護劑與/或農藥,與/或加強活性之佐劑, 如.滲透劑,其貫例為植物油類,例如:菜籽油、葵花油, ,物油類’例如:液態石壤,植物脂肪酸之烧基酷類,如·· 菜籽油或大旦油甲酯類,或烷醇烷氧化物,與/或擴散劑, 例如基石夕氧燒與/或鹽類,其實例為有機或無機铵或鱗 鹽,其實例為硫酸銨或磷酸氫二銨,與/或促進滞留劑,如: 磺基琥珀酸二辛酯或羥基丙基關華豆膠聚合物與/或保濕 劑,例如:甘油與/或肥料,如:銨、鉀或磷肥料。 典型之調配物實例包括水溶性液體(SL)、可乳化濃縮 劑(EC)、水基乳液(EW)、懸浮濃縮劑(sc、SE、FS、OD)、 水可分散性粒劑(WG)、粒劑(GR)及膠囊濃縮劑(CS);此等及 其他可能之調配物型式說明於例如:由2004年FAO/WHO 聯合農藥會議(FAO/WHO Joint Meeting on Pesticide Specifications)所製作之” FAO植物生產與保護報告 -173(FAO Plant Production and Protection Papers - 173)中 之”國際作物生命與農藥說明,FAO與WHO農藥說明之發 展及用法手冊(Crop Life International and in Pesticide Specifications, Manual on development and use of FAO and 48 201136518 WHO specifications for pesticide),ISBN : 9251048576。該 調配物中除了一種或多種本發明活性成份外’尚可包含農 化化合物。 該調配物或最好包含辅助物質,如:增量劑、溶劑、 自發性促進劑、載劑、乳化劑、分散劑、防珠劑、殺生物 製劑、增稠劑與/或其他輔助物質,例如:佐劑。本文中, 佐劑為加強調配物生物效應之組成份,該組成份本身不需 具有生物效應。佐劑實例為促進滯留、擴散、附著在葉表 面、或促進滲透之製劑。 活性成份可轉換成慣用調配物,如:溶液、乳液、可 濕化粉劑、水性與油性懸浮液、粉劑、塵粉劑、糊劑、可 溶性粉劑、可溶性粒劑、撒播用粒劑、懸浮_乳液濃縮物、 /文飽活性成伤之天然材料與浸飽活性成份之合成材料、肥 料及含在聚合材料中之微包囊物。 迫頌洞孤视诉m匕知方式製備,例如:混合活性化合 物與增量劑’亦即液體溶劑及/或㈣載劑,視需要可使; 界面活性劑,亦即乳化劑與/或分散劑與/或發泡劑。調配物 製法係在施用前或施用期間於合適設備中進行。 可使用之辅助物質為彼等適合對活性成份之調配物盘 ^由此等調配物製成之施用型式(例如:農藥或保護作物組 『物,如.喷減或拌種劑)職與特殊性質,如 性質與/或特殊生物性質之物f。典叙合適物j術 增量劑、溶劑與載劑。 物質為· 合適之增量劑為例如. X、極性與非極性有機化學液 49 201136518 體。例如:芳香系與#芳香系烴類(如:鏈烷烴、烷基苯、 烧基萘、氣苯)、醇類與多元醇(若適當時,亦可經取代、趟 化與/或酯化)、酮類(如:丙酮、環己酮)、酯類(包括脂肪類 與油類)與(聚)醚類、未取代與經取代之胺類、酿胺類、内 醯胺類(如:N-烷基吡咯啶酮)與内酯類、砜類與亞砜類(如: 二甲亞碾)。 原則上,可以使用所有合適之溶劑。當使用水作為增 量劑時,亦可使用例如:有機溶劑作為輔助溶劑。基本上 適用之液態溶劑為:芳香族,如:二甲苯、甲苯或烷基萘 類、氣化芳香烴與氣化脂族烴類,如:氯苯、氯化乙烯或 二氣甲院,脂族烴類,如:環己烧或鏈烧烴,例如:石油 分顧物、礦物油與植物油,醇類,如:丁醇或甘醇及其醚 類與酯類,酮類,如:丙酮、甲基乙基酮、甲基異丁基酮 或環已酮,強極性溶劑,如:二曱亞砜,及水。 原則上,可以使用所有合適之載劑。合適之固態載劑 尤指: 例如.銨鹽及天然礦物磨粉,如:高嶺土、黏土、滑 石、白堊、石英、美國活性白土、蒙脫土或矽藻土,及合 成物質磨粉’ 士口 :高分散度石夕石、礬土與石夕酸鹽;適用為 粒劑之Site載劑為例如:粉碎與分碎天然礦石,如:方解 石、大理石、浮石、海泡石與白雲石,及無機與有機磨粉 之合成顆粒’及有機物質顆粒,如:紙、鑛肩、挪子殼、 玉米穗與煙草桿。 亦可使用液化氣態增量劑或溶劑。尤其合適之彼等增 50 201136518 量劑或㈣翁鮮溫度及解動下I氣態者,例如: 氣霧劑推進氣體’如:鹵烴類,及丁p 氧化碳 久j沉、丙烷、氮氣及二 Μ離子性或非離子性性質之乳化劑與/或發泡劑、分 散劑或潤關或此等界面活性船&合物之實例為例如 丙烯酸之鹽類、木質素魏H祕雜或萘錯酸之 鹽類、環氧乙㈣麟醇或與脂贿或與麵胺、盘 代之苯斷較佳為縣糾料基如)之雜合物、崎基破 賴酉旨之鹽類、牛石黃酸衍生物(較佳為牛確酸燒基扑聚乙^ 氧基化醇或苯酚之磷酸酯、多元醇之脂肪酸酯,及含硫酸 根、磺酸根與磷酸根之化合物之衍生物,例如:烷基芳美 聚二醇醚、烷基磺酸鹽、烷基硫酸鹽、芳基磺酸鹽、蛋= 質水解物、木質素亞硫酸鹽廢液及曱基纖維素。若其中一 種活性成份與/或其中一種惰性載劑為水不可溶且若該施 用方式係在水中進行時,則宜含有界面活性物質。 適用之乳化劑與/或發泡劑為例如:非離子性與陰離子 性乳化劑,如.聚氧乙烯脂肪酸酯、聚氧乙稀脂肪醇鱗, 例如·烧芳基聚一醇喊類、烧基續酸鹽、烧基硫酸鹽、芳 基石黃酸鹽及蛋白質水解產物;合適分散劑為非離子性與/或 離子性物質,例如:來自醇-ΡΟΕ與/或POP醚類、酸與/或 Ρ0Ρ-Ρ0Ε g旨類、烷基-芳基與/或p〇p_p〇E醚類、脂肪-與/ 或Ρ0Ρ-Ρ0Ε加成物、P0E-與/或POP-多元醇衍生物、ρ〇Ε· 與/或POP-山梨糖醇酐或-糖加成物、硫酸烷基酯或硫酸芳 基酯、磺酸烷基酯或磺酸芳基酯,與磷酸烷基酯或磷酸芳 51 201136518 基知,或相應之p〇-醚加成物。本文中,p〇p意指聚氧丙 烯氧化物,P0E意指聚氧乙婦氧化物,p〇意指氧化丙稀, 及PE意指帛氧乙燒。此外,亦可使用合適之寡聚物或聚合 物,例如·彼等由乙烯基單體、丙烯酸、E〇與/或p〇單獨 或組合,例如4聚)醇類或(聚)胺類所衍生之寡聚物或聚合 物。此外亦可使用木質素與其磺酸衍生物、未修飾與經修 飾之纖維素、芳香系與/或脂系磺酸類及其與曱醛之加成 物。 調配物中可使用膠黏劑,如:羧曱基纖維素、呈粉末、 顆粒或膠乳型式之天然與合成聚合物 ,如:阿拉伯膠、聚 乙烯醇與聚雜乙烯g旨’及天鋪脂如:腦雜與印破脂, 及合成磷脂。 亦可使用著色劑,如:無機色素(例如:氧化鐵,氧化 鈦與普魯士藍)及有機染料,如:茜素染料 ,偶氮染料及金 駄^月木料’及微量營養素如:鐵、錳、硼、銅、鈷、 錮與鋅之鹽類^ 若適W時’ δ周配物及其所衍生之施用方式中亦包含其 ^加劑。其他可能之添加劑為芳香成份 、可視需要改質 錯、^ Μ植物Ί 營養素(包括微量營養素),如: 禾孟删鋼、姑、銷與鋅之鹽類。其他添加齊!為例如: 、、矢:卞丨保濩性膠體、結合劑、黏著劑、增稠劑、搖溶物質、 W文疋劑、螯合劑、錯合劑、保濕劑、 馈政劑。通常,法,14 #八 能+ Γ生成知可併用任何常用於調配目的之固 態或液態添加劑。 52 201136518 亦可包括安定劑,如:低溫安定劑、防腐劑、抗氧化 劑、光安定劑或其他改善化學/物理安定性之製劑。 合適之促進滯留劑包括例如:所有彼等可降低動態表 面張力之物質,如:4基琥賴二辛s旨,或可提高黏彈性 之物質,如:羥基丙基關華豆膠聚合物。 本文中合適之滲透劑包括所有彼等常用於加強活性農 化化合物滲透進人植物之物質。本文中,渗透劑之定義為 k(通㊉為水性)施用液體與/或從噴灑覆層開始,可以滲入 植物之角質層,藉以提高活性成份在角質層中之移動性。 此性質可採敎獻中曾說明之方法決定(Baui:等人,1997, Pesticide Science 51,13M52)。其實例包括例如:醇烷氧化 物,如:椰子脂肪乙氧化物(10)或異十三烷基乙氧化物 (12)、脂肪酸酯,如.菜籽油或大豆油曱酯、脂肪胺烷氧化 物,如:獸脂胺乙氧化物(15),或銨與/或鱗鹽類,如:硫 酸ί安或填酸氫一叙。 基於調配物之重量計,該調配物較佳為包含 法性成份,更佳為至95重 〇.__〇丨至98重量%^ 90重量%之活性成份。 量%之活性成份’最佳為商業調配物、由此等調配物製成 活性成份可呈其標準生、成份(如:殺昆蟲劑、引 之施用型式存在、與其=殺壁卵、殺線Α劑、殺真菌 誘劑、不孕劑、殺細菌#1 劑、肥料、化學信息物質) 劑、生長調節劑、除草刻、 n 或與W植物性質之形性成份亦可呈其標 當作為殺昆蟲劑使用 53 201136518 準調配物商品形式及由此調配物製成之施用形式,與增效 劑形成混合物。增效劑意指可提高活性成份之活性,但所 添加增效劑本身不一定有活性之化合物。 當作為殺昆蟲劑使用時,根據本發明之活性成份亦可 呈其標準調配物商品形式及由此調配物製成之施用形式, 與可在施用至植物環境中、植物植株表面上或植物組、織中 後降低活性成份降解之抑制劑形成混合物。 * 由標準調配物商品製成之施用形式(農藥)中之活性成 份含量可在很大範圍内變化。以施用形式之重晋斗 里5T,施用 形式之活性成份濃度可為〇.〇〇〇〇〇〇01至95重量% 、 份’較佳為0.00001至1重量%之範圍内。 ‘ 可依適合施用形式之一般方法施用。 使用本發明活性成份處理植物與植株部份之方法( 傳統處理法直接處理或仙在其環境、棲息地或庫 間’例如:浸泡、喷壤、喷霧、灌注、蒸發、撒粉予工 撒?、起泡、塗刷、擴散、注射、洗水(浸藥)、點滴灌概: 及右處理繁㈣料時,尤其在處理種子時,亦# 拌種法、濕式拌種法、料拌種法、包被 二 ,,等等。亦可採用超低體積法配置活性:層= 土壌中注脑性絲製«活性絲本身。 或在 直接處理植物之較佳方法為葉部施 發明活性成份至葉部,此時可 / 用本 調整處理頻率及施用率。 将疋。蟲之肆虐程度 若為全株作用性活性化合物時,本發明活性成份可經 54 201136518 由根部結構進入植物體。此時,以本發明活性成份作用在 植物所在地之方式處理植物。其作法為例如:浸藥,或混 合至土壤或營養素溶液中,亦即使植物位置(例如:土壤或 水耕系統)浸泡在液體型式之本發明活性成份中,或採用土 壤施用法,亦即將本發明活性成份以固體型式(例如:粒劑 型式)引入植物位置。若處理水稻作物時,其亦可定量添加 呈固體施型式之本發明化合物(例如:呈粒劑型式)至水田 中。 本發明活性成份可呈其本身或呈其調配物型式使用, 亦可與已知殺真菌劑、殺細菌劑、殺壁蝨劑、殺線蟲劑或 殺昆蟲劑混合使用,因此可以例如擴大作用範圍或阻止發 展出抗性。許多例子中,可得到促效性效應,亦即混合物 之效力高於個別化合物之效力總和。 適用之混合對象包括例如下列化合物: 殺昆蟲劑/殺壁蝨劑/殺線蟲劑: 本文以俗名指出之活性成份係已知者且說明於例如: 農藥手冊(“The Pesticide Manuar‘第 14 版,British Crop Protection Council 2006)或可於網際網路上查尋(例如: http : //www.alanwood.net/pesticides) 〇 (1)乙醯基膽鹼酯酶(AChE)抑制劑,例如: 胺曱酸酯類,例如:安利卡(alanycarb)、得滅克 (aldicarb)、本得卡(bendiocarb)、本伏卡(benfuracarb)、布卡 辛(butocarboxim)、丁氧布卡辛布卡辛(butoxycarboxim)、加 55 201136518 保利(carbary 1)、加保扶(carbofuran)、丁基加保扶 (carbosulfan)、抑芬卡(ethiofencarb)、芬布卡(fenobucarb)、 覆滅蜗(formetanate)、伏赛卡(furathiocarb)、滅必益 (isoprocarb)、滅賜克(methiocarb)、納乃得(methomyl)、滅 特卡(metolcarb)、歐殺滅(oxamyl)、比加普(pirimicarb)、安 丹(propoxur)、硫敵克(thiodicarb)、硫芬斯(thiofanox)、三 辛滅(triazamates)、三滅卡(trimethacarb)、XMC 與賽利卡 (xylylcarb);或 有機稱酸S旨類,例如:歐殺松(acephate)、亞滅伏 (azamethiphos)、谷速松(azinphos)(-曱基、-乙基)、卡速松 (cadusafos)、氣乙松(chlorethoxyfos)、氣芬松 (chlorfenvinphos)、氯滅松(chlormephos)、陶斯松 (chlorpyrifos)(-曱基)、庫伏斯(coumaphos)、氰乃松 (cyanophos)、滅賜松(demeton)-S-曱基、大利松(diazinon)、 二氯松(dichlorvos)/DDVP、雙特松(dicrotophos)、大滅松 (dimethoate)、大芬松(dimethylvinphos)、二硫松 (disulfoton)、EPN、愛殺松(ethion)、普伏松(ethoprophos)、 凡伏(famphur)、芬滅松(fenamiphos)、撲滅松(fenitrothion)、 芬殺松(fenthion)、福賽特(fosthiazate)、飛達松 (heptenophos)、抑伏松(isofenphos)、0-(曱氧基胺基硫代填 醯基)水楊酸異丙基醋、抑殺松(isoxathion)、馬拉松 (malathion)、滅加松(mecarbam)、達馬松(methamidophos)、 滅大松(methidathion)、美文松(mevinphos)、亞素靈 (monocrotophos)、乃立松(naled)、歐滅松(omethoate)、歐滅 56 201136518 賜松(oxydemeton)-曱基、巴拉松(parathi〇n)(-曱基)、賽達松 (phenthoate)、福瑞松(phorate)、裕必松(phosalone)、益滅松 (phosmet)、福賜米松(phosphamidon)、辛硫鱗(phoxim)、亞 特松(pirimiphos)(-甲基)、佈飛松(profenofos)、普丹松 (propetamphos)、普硫松(pr〇thiofos)、必伏松(pyradofos)、 必芬松(pyridaphenthion)、拜裕松(quinalphos)、速伏特 (sulfotep)、特必松(tebupirimfos)、亞培松(temephos)、託福 松(terbufos)、四氯松(tetrachlorvinphos)、硫滅松 (thiometon)、三落松(triazophos)、三氯松(triclorfon)與繁米 松(vamidothion) (2) GABA-閘控之氣離子通道擷抗劑,例如: 有機氣’例如:克丹(chlordane)與安殺番 (endosulfan)(cc-);或 飛普洛類(Fiprols),例如:抑普洛(ethiprole)、芬普洛 (fipronil)、帕普洛(pyrafluprole)與普洛(pyriprole)。 (3) 鈉通道調節劑/依賴電壓之鈉通道阻斷劑,例如: 擬除蟲菊S旨類,例如:阿納寧(acrinathrin)、亞特靈 (allethrin)(d-順式-反式,d-反式)、畢芬寧(bifenthrin)、必利 靈(bioallethrin)、必利靈(bioallethrin)_S-環戊烯基、必賽靈 (bioresmethrin)、乙氰菊酯(CyCl〇prothrin)、赛扶寧 (cyfluthrin)((-)、賽洛寧(cyhalothrin)((-、(-)、賽滅寧(cypermethrin)(a-、β. ' θ-、ζ-)、賽芬寧(cyphenothrin)[(lR)-反式異構物]、第滅寧(deltamethrin)、第 57 201136518 芬寧(dimefluthrin)、依普靈(empenthrin)[(EZ)-(lR)-異構物]、益化利 (esfenvalerate)、依芬寧(etofenprox)、芬普寧(fenpropathrin)、芬化利 (fenvalerate) ' 福本赛寧(flucythrinate) ' 伏滅寧(flumethrin)' 福化 利(fluvalinate)((-)、海本斯(halfenprox)、益普靈(imiprothrin)、滅 伏特靈(metofluthrin)、百滅寧(permethrin)、芬特寧 (phenothrin)[(lR)-反式異構物]、普烈靈(prallethrin)、普伏靈 (profluthrin)、除蟲菊酯(pyrethrins(pyrethrum))、利滅靈 (resmethrin)、RU-15525、希拉芬(silafluofen)、特伏靈 (tefluthrin)、特滅靈(tetramethrin)[(lR)-異構物]、泰滅寧 (tralomethrin)、參伏靈(transfluthrin)與 ZXI 8901 ;或 DDT ;或美克氣(methoxychlor)。 (4) 菸鹼激導性乙醯基膽鹼受體增效劑,例如: 類新於驗類,例如:乙醯普(acetamiprid)、克利定 (clothianidin)、第諾芬(dinotefuran)、益達胺(imidacloprid)、 尼普爛(nitenpyram)、硫克比(thiacloprid)、赛速安 (thiamethoxam);或 尼古丁。 (5) 異位性乙醯基膽鹼受體調節劑(增效劑),例如: 速必辛類(Spinosyns) ’例如:賜特能(Spinet〇ram)與賜 諾殺(spinosad)。 (6) 氣離子通道活化劑’例如: 58 201136518 抑滅克定類(avermectins)/美保徽素(milbemycin),例 如:艾滅克定(abamectin)、抑滅克定(emamectin)苯曱酸鹽、 利滅克定(lepimectin)與美保克定(milbemectin)。 (7) 幼保激素擬似物,例如:赫普靈(hydroprene)、克普靈 (kinoprene)、滅普靈(methoprene)或吩克卡(fenoxycarb);必 普芬(pyriproxifen) ° (8) 作用機轉未知或非專一性之活性成份,例如:發煙劑, 例如:甲基溴及其他烷基鹵化物;或 氯0比靈(chloropicrin);硫醯氟;删砂;酒石酸録鉀鹽。 (9) 選擇性抗攝食劑,例如:必滅辛(pymetrozine)或伏卡滅 (flonicamid) ° (10) 蜗生長抑制劑,例如:克芬辛(clofentezine)、地伏辛 (diflovidazin)、海賽嗤(hexythiazox)、抑特唾(etoxazole)。 (11) 昆蟲腸膜之微生物瓦解劑,例如:蘇雲金芽胞桿菌以色 列亞種认wWng/e«幻)subspecies /srae/e/wW、球形 芽孢桿菌(万aczY/w·? 叹/zaeWcwW、蘇雲金芽胞桿菌鮎澤亞種 (5〇^7/奶 i/zwWwgz’ews/s subspecies in.zGwaz)、蘇雲金芽胞桿菌 庫斯塔基亞種(5acz7/w·? Awr/wgz’e似b subspecies如以如切、 蘇雲金芽胞桿菌殺蟲亞種CSaczY/ws «价subspecies 59 201136518 ί⑼,與BT植物蛋白質,例如:CrylAb、CrylAc、 CrylFa、Cry2Ab、mCry3A、Cry3Ab、Cry3Bb、Cry34/35Abl。 (12) 氧化性磷酸化反應抑制劑,ATP瓦解劑,例如:地芬能 (diafenthiuron);或 有機錫化合物’例如:亞赛錫(azocyclotin)、赛赫錫 (cyhexatin)、芬塔錫(fenbutatin)氧化物;或 歐蜗多(propargite);特達芬(tetradifon)。 (13) 干擾H-質子梯度之氧化性磷酸化反應之去偶合劑,例 如:克S4b(chlorfenapyr)與 DNOC。 (14) 於驗激導性乙醯基膽驗受體擷抗劑,例如:本速達 (bensultap)、培丹(cartap)(鹽酸鹽)、硫克蘭(thiocylam)與硫 速伏(thiosultap)(鈉鹽)。 (15) 幾丁質生合成抑制劑,第〇型,例如:苯曱醯基脲類, 例如:必赛伏(bistrifluron)、克伏能(chlofluazuron)、地伏能 (diflubenzuron)、伏赛能福環脲(flucyci〇xuron)、氟芬隆 (flufenoxuron)、赫姆能(hexaflumuron)、利芬能(lufenuron)、 利化能(novaluron)、諾化能(noviflumuron)、特速能 (teflubenzuron)與三伏能(triflumuron)。 (16) 幾丁質生合成抑制劑,第i型,例如:佈芬辛 201136518 (buprofezin) ° (17) 蜆變瓦解劑,例如^赛麻辛(cyromazine)。 (18) 脫皮激素增效劑/瓦解劑,例如: 二醯基肼類,例如:克麻賽(chromafenozide)、赫芬賽 (halofenozide)、曱氧芬赛(methoxyfenozide)與特芬赛 (tebufenozide) ° (19) 章魚胺激導性增效劑,例如:三亞蜗(amitraz)。 (20) 複合物-III電子傳遞抑制劑,例如:海滅能 (hydramethylnone);亞克希(acequinocyl);伏克靈 (fluacrypyrim)。 (21) 複合物_1電子傳遞抑制劑,例如:選自METI殺壁蝨劑 之群中,例如: 芬赛昆(fenazaquin)、芬普赛滅(fenpyroximate)、普靈芬 (pyrimidifen)、必達本(pyridaben)、達芬必(tebufenpyrad)、 特芬必(tolfenpyrad) ;或魚藤精(rotenone)(Derris)。 (22) 依賴電壓之鈉通道阻斷劑,例如:英賽普(jnd〇xacarb); 滅伏美松(metaflumizone)。 201136518 (23) 乙醯基_CG_A紐酶之抑制劑,例如:季酮酸衍生物, 例如:螺克芬(Spir〇dicl0fen)與螺滅芬(spir_sifen);或吡 洛酮酸衍生物’例如:螺特滅(spir〇tetramat)。 (24) 複合物-IV電子傳遞抑制劑,例如:膦類,例如:填化 鋁、磷化鈣、膦、磷化辞;或氰化物。 (25) 複合物-II電子傳遞抑制劑,例如:氰必吩 (cyenopyrafen) ° (28)蘭尼鹼(ryanodin)受體效應劑,例如:二醯胺類,例如: 氣蒽0比 σ各(chlorantraniliprole)(Rynaxypyr)、氰胺0比洛 (cyantraniliprole)(Cyazypyr)及 3-溴-N-{2-溴-4-氣-6-[(1 _環 丙基乙基)胺曱醯基]苯基}-1-(3-氣吼啶-2-基)-1Η-η比唑-5-羧 醯胺(自 W02005/077934 中已知)或 2-[3,5-二溴-2·({[3-溴 -1-(3-氯吡啶-2-基)-1Η-吡唑-5-基]羰基}胺基)苯曱醯 基]-1,2-二甲基肼羧酸曱酯(自W02007/043677中已知)。 其他具有未知作用機轉之活性成份,例如:查得定 (azadirachtin)、安伏滅(amidoflumet)、苯賽滅 (benzoximate)、必芬賽(bifenazate)、蜗離丹 (chinomethionat)、克利得(cryolite)、赛特芬(cyflumetofen)、 大克蜗(dicofol)、伏速吩(fluensulfone)(5-氣-2-[(3,4,4-三氟 丁-3-烯-1-基)磺醯基]-1,3-噻唑)、伏吩靈(flufenerim)、必達 62 201136518 利(pyridalyl)與必伏松(pyrifluquinazon);及基於芽孢桿菌 (Bacillus firmus)之產品(1-1582, BioNeem,Votivo)及下列已 知活性成份: 4-{[(6-溴》比啶-3-基)曱基](2-氟乙基)胺基}呋喃-2(5H)-酮(自WO 2007/115644中已知)、4-{[(6-氟吡啶-3-基)曱 基](2,2-二氟乙基)胺基}呋喃·2(5Η)-酮(自WO 2007m5644 中已知)、4-{[(2-氯-1,3-噻唑-5-基)曱基](2-氟乙基)胺基}呋 喃-2(5H)-酮(自 WO 2007/115644 中已知)、4-{[(6-氯吡啶-3-基)曱基](2-氟乙基)胺基}呋喃_2(5H)_酮(自WO 2007/115644中已知)、4-{[(6-氣吡啶-3-基)曱基](2,2-二氟乙 基)胺基}呋喃-2(5H)-酮(自WO 2007/115644中已知)、 4-{[(6-氯-5-氟吡啶-3-基)曱基](曱基)胺基}呋喃·2(5Η)-酮 (自 W0 20〇7/ll5643 中已知)、4_{[(5,6_二氣吡啶_3_基)甲 基](2-氟乙基)胺基}呋喃-2(5H)-酮(自WO 2007/115646中已 知)、4_{[(6_氣-5-氟吼啶-3-基)曱基](環丙基)胺基}呋喃 -2(5H)-酉同(自 WO 2007/115643 中已知)、4-{[(6-氯吡啶-3- 基)曱基](環丙基)胺基}吱喃_2(5H)-酮(自ΕΡ-Α-0 539 588中 已知)、4_{[(6_氣吡啶_3_基)曱基](曱基)胺基}。夫喃_2(5H)_酉同 (自ΕΡ-Α-0 539 588中已知)、[(6-氯吡啶-3-基)曱基](曱基) 氧撐基-λ4-亞硫基氰醯胺(自WO 2007/149134中已知)、 0(6-氯吼啶-3-基)乙基](曱基)氧撐基_λ4_亞硫基氰醯胺(自 WO 2007/149134中已知)及其非對映異構物(Α)及(Β) 63 201136518
ch3
1 T ο Λ N CI^N^ iN (A) (亦自WO 2007/149134中已知)、[(6-三氟曱基吡咬_3_ 基)曱基](曱基)氧撐基-λ4-亞硫基氰醯胺(自 w〇 2007/095229 中已知)、速伏樂(sulfoxaflor)(亦自 w〇 2007/149134中已知)、11-(4-氣-2,6-二曱基苯基)-12-經基 -1,4-二氧雜-9-氣雜二螺[4.2.4.2]十四碳-11-稀-10-嗣(自 WO 2006/089633 中已知)、3-(4·-氟-2,4-二曱基聯笨-3-基)_4-羥基-8-氧雜-1-氮雜螺[4.5]癸-3-烯-2-酮(自 WO 2008/067911 中已知)、1-[2-氟-4-曱基-5-[(2,2,2-三氟乙 基)亞磺醯基]苯基]-3-(三氟曱基)-1Η-1,2,4-三唑-5-胺(自 WO 2006/043635 中已知)、環丙烧緩酸 [(38,4&11,1211,12&3,12匕3)-3-[(環丙基羰基)氧]-6,12-二羥基 -4,12b-二 曱 基-11-酿I 基-9-( π 比咬 _3-基)-1,3,4,4&,5,6,63,12,12\121>十氫-211,111^苯并[£]哌喃并 [4,3-b]色烯-4-基]曱基酯(自 WO 2006/129714)、2-氰基-3-(二 氟曱氧基)-N,N-二曱基苯續酿胺(自W02006/056433中已 知)、2-氰基-3-(二氟曱氧基)-N-曱基苯續醯胺(自 W02006/100288中已知)、2-氰基-3-(二氟曱氧基)-Ν·乙基苯 磺醯胺(自W02005/035486中已知)、4-(二氟曱氧基)-Ν-乙 基-Ν-曱基-1,2-苯弁β塞唾-3-胺 1,1-二氧化物(自 64 201136518 W02007/057407 中已知)及 N-[l-(2,3-二曱基苯基)-2-(3,5-二曱基苯基)乙基]-4,5-二氫-1,3-噻唑-2-胺(自 W02008A04503 中已知)。 殺真菌劑 (1)麥角固醇生合成抑制劑,例如:艾狄莫(aldimorph)、阿 克嗤(azaconazole)、拜坦諾(bitertanol)、布康口生 (bromuconazole)、西普康唾(cyproconazole)、二氯丁0坐 (diclobutrazole)、地吩康嗤(difenoconazole)、地康0來 (diniconazole)、地康吐-M、得莫(dodemorph)、得莫乙酸鹽、 環氧克嗤(epoxiconazole)、抑達σ坐(etaconzole)、芬利莫 (fenarimol)、芬康嗤(fenbuconazole)、吩酿胺(fenhexamide)、 芬普定(fenpropidin)、芬普福(fenpropimorph)、伏克康0生 (fluquinconazole)、伏米得(flui*primidol)、 護石夕得(flusilazole)、護汰芬(flutriafol)、伏康0生 (furconazole)、順式伏康嗤、赫康坐(hexaconazole)、依滅列 (imazalil)、依滅列硫酸鹽、抑本康嗤(imibenconazole)、抑 普康唾(ipconazole)、滅康》坐(metconazole)、麥克坦尼 (myclobutanil)、納得吩(naftifin)、紐莫(nuarimol)、D寻康峻 (oxpoconazole)、 巴克素(paclobutrazole)、比菲°坐(pefurazoate)、本康0坐 (penconazole)、旅布靈(piperalin)、撲克樂(prochloraz)、普 克利(propiconazole)、普赛康《坐(prothioconazole)、必達克 (pyributicarb)、比芬斯(pyrifenox)、克康《^(quinconazole)、 65 201136518 辛康唑(simeconazole)、賜必安(spiroxamine)、得克利 (tebuconazole)、特本吩(terbinafin)、特康唾(tetraconazole)、 三泰芬(triadimefon)、三泰隆(triadimenol)、賽得莫 (tridemorph)、三伏唑(triflumizole)、賽福寧(triforine)、三 狄康唑(triticonazole)、優康唑(uniconazole)、優康唑-P、芬 克唑(viniconazole)、福康唑(voriconazole)、1-(4-氯苯 基)-2-(1Η-1,2,4-三唑-1-基)環庚醇、1-(2,2-二曱基-2,3-二氫 -1H-茚-1-基)-1Η-咪唑-5-羧酸曱酯、Ν·-{5-(二氟曱基)-2•甲 基·4-[3-(三曱基矽烷基)丙氧基]苯基}-Ν-乙基-Ν-曱基亞胺 基-曱醯胺、Ν-乙基-Ν-甲基-Ν'-{2-曱基-5-(三氟甲 基)-4-[3_(三曱基矽烷基)丙氧基]-苯基}_亞胺基曱醯胺與 〇-[1-(4-曱氧基苯氧基)-3,3-二曱基丁-2-基]-1Η-咪唑-1-硫 代曱酸。 (2)呼吸抑制劑(呼吸鍵抑制劑),例如:必賽吩(bixafen)、保 卡利(boscalid)、卡布辛(carboxin)、地伏滅靈 (diflumetorim)、芬伏爛(fenfuram)、護派搞(fluopyram)、護 坦尼(flutolanil)、護賽保(fluxapyroxad)、福滅普 (furametpyr)、福滅克(furmecyclox)、抑本散(isopyrazam)之 順-差向異構性消旋物1RS,4SR,9RS與反-差向異構性消旋 物1RS,4SR,9SR混合物、抑本散(isopyrazam)(反差向異構 性消旋物)、抑本散(iS〇pyrazam)(反-差向異構性對映異構物 1R,4S,9S)、抑本散(iSOpyrazam)(反-差向異構性對映異構物 1S,4R,9R)、抑本散(iSOpyrazain)(順-差向異構性消旋物 66 201136518 1RS,4SR,9RS)、抑本散(isopyrazam)(順-差向異構性對映異 構物1R,4S,9R)、抑本散(isopyrazam)(順-差向異構性對映異 構物 1S,4R,9S)、米普尼(mepronil)、嘉得信(oxycarboxin)、 本福吩(penflufen)、本賽能(penthiopyrad)、速達散 (sedaxane)、地伏醯胺(thifluzamide)、1-曱基-N-[2-(l,l,2,2-四氟乙氧基)苯基]-3-(三氟曱基)-111-°比唑-4-曱醯胺、3-(二 氟曱基)-1-甲基-N-[2-(l,l,2,2-四氟乙氧基)苯基]-iH-n比唑 -4-曱醯胺、3-(二氟曱基)-N-[4-氟-2-(1,1,2,3,3,3-六氟丙氧基) 苯基]-1-曱基-1H-吡唑-4-曱醯胺與N-[l-(2,4-二氣苯基)-1-曱氧基丙-2-基]-3-(二氟曱基)-1-甲基-1H-吡唑-4-曱醯胺。 (3)對呼吸鏈複合物III之呼吸抑制劑(呼吸鏈抑制劑),例 如:辛唆响菌胺(ametoctradin)、安美速(amisulbrom)、亞托 敏(azoxystrobin)、赛發滅(cyazofamid)、醚菌胺 (dimoxystrobin)、烯月亏菌酯(enestrobin)、芬色丹 (famoxadone)、芬滅酮(fenamidone) 、 IL 喷菌醋 (fluoxastrobin)、趟菌酷(kresoxim-methyl)、笨氧菌胺 (metominostrobin)、將醚菌胺(orysastrobin)、〇定氧菌酉旨 (picoxystrobin)、〇坐菌胺酯(pyraclostrobin)、唾胺菌醋 (pyrametostrobin)、0坐菌酯(pyraoxystrobin)、°比菌苯威 (pyribencarb)、三氟敏(trifloxystrobin)、(2E)_2-(2-{[6-(3-氯 -2-曱基苯氧基)_5_氟嘧啶-4-基]氧}苯基)-2-(曱氧基亞胺 基)-N-甲基-乙醯胺、(2E)-2-(曱氧基-亞胺基曱基 -2·(2-{[({(1Ε)_1_[3·(三氟曱基)苯基]-亞乙基}胺基)氧]曱 67 201136518 基卜笨基)乙醯胺、(2Ε)-2·(曱氧基亞胺基>N_曱基 -2-{2-[(Ε)-({1-[3-(三氟曱基)笨基]乙氧基}亞胺基)曱基]苯 基}乙醯胺、(2E)-2-{2-[({[(lE)-l_(3-{[(E)-l-氟-2-苯基乙烯 基]氧}苯基)亞乙基]胺基}氧)甲基]苯基卜2_(曱氧基亞胺 基)-N-曱基乙醯胺、(2E)-2-{2-[({[(2E,3E)-4-(2,6-二氯苯基) 亞丁-3-烯-2-基]胺基}-氧)甲基]笨基卜2_(曱氧基亞胺基)_N_ 曱基乙醯胺、2-氯-Ν·(1,1,3-三甲基_2,3_二氫_1Η,_4·基)吡 啶-3-曱醯胺、5-曱氧基-2-曱基_4-(2-{[({(1Ε)-1-[3-(三氟-甲 基)苯基]亞乙基}胺基)氧]曱基}苯基)_2,4_二氫-3Η-1,2,4-三 唑-3-酮、(2Ε)-2-{2-[({環丙基甲氧基苯基)亞胺基]曱基} 硫基)曱基]苯基}-3-甲氧基-丙-2-丙烯酸甲酯、Ν·(3-乙基 -3,5,5-三曱基環己基)-3-(曱醯基胺基)_2·經基苯甲醯胺、 2-{2-[(2,5-二曱基苯氧基)曱基]苯基}_2_曱氧基·ν·曱基乙 醯胺與(2R)-2-{2-[(2,5-二曱基-苯氧基)曱基]苯基卜2_曱氧 基-N-曱基乙醯胺。 (4)有絲分裂與細胞分化之抑制劑,例如:免賴德 (benomyl)、卡苯辛(carbendazim)、氯吩。坐(chlorfenazole)、 地吩卡(diethofencarb)、噻唑菌胺(ethaboxam)、氟吡菌胺 (fluopicolid)、伏塔唑(fuberidazole)、賓克隆(pencycuron)、 腐絕(thiabendazole)、曱基多保淨(thiophanate-methyl)、多 保淨(thiophanate)、索醯胺(zoxamide)、5-氯-7-(4-甲基娘口定 -1-基)-6-(2,4,6-三氟苯基)-[1,2,4]三〇坐并[l,5-a]e密咬與3-氣 -5_(6-氣°比〇定-3-基)-6-曱基-4-(2,4,6-二氣苯基)塔〇井。 68 201136518 (5) 具多重位置活性之化合物,例如:波爾多(Bordeaux)混 合物、四氯丹(captafol)、蓋普丹(captan)、四氯異苯腈 (chlorothalonil)、銅製劑,如:氫氧化銅、萘甲酸銅、氧化 銅、驗性氣氧化銅、硫酸銅與益發靈(dichlofluanid)、腈硫 醌(dithianon)、多寧(dodine)、多寧游離鹼、富爾邦(ferbam)、 護福爾培(fluorofolpet)、福爾培(folpet)、免熱淨 (guazatine)、免熱淨乙酸鹽、抑克定(iminoctadine)、抑克定 苯烧石黃酸鹽(iminoctadine albesilate)、抑克定(iminoctadine) 三乙酸鹽、猛銅(mancopper)、猛粉克(mancozeb)、猛乃浦 (maneb)、滅得賴(metiram)、滅得賴鋅鹽、快得寧 (oxine-copper)、丙氧苯脒(propamidine)、曱基鋅乃浦 (propineb)、硫與硫製劑,例如:多硫化|弓、得恩地(thiram)、 特伏奈(tolylfuanid)、鋅乃浦(zineb)與益穗(ziram)。 (6) 抗性誘發劑,例如:艾苯拉(acibenzolar)-S-甲基、異°塞 菌胺(isotianil)、撲殺熱(probenazole)與地得尼(tiadinil)。 (7) 胺基酸與蛋白質生合成抑制劑,例如:安得靈 (andoprim)、保米黴素(blasticidin)-S、嘧菌環胺 (cyprodinil)、賜徽素(kasugamycin)、賜徽素鹽酸鹽水合物、 米本靈(mepanipyrim)與比坦尼(pyrimethanil)。 (8) ATP生產抑制劑,例如:三苯醋錫(fentin acetate)、三苯 69 201136518 氣錫(fentin chloride)、三苯錫氫氧化物(fentin hydroxide)與 石夕硫吩(silthiofam)。 (9) 細胞壁合成抑制劑,例如:苯賽卡(benthiavalicarb)、地 滅莫(dimethomorph)、伏莫(flumorph)、抑發利 (iprovalicarb)、曼普胺(mandipropamid)、保粒黴素 (polyoxins)、保粒靈(polyoxorim)、瓦利黴素(validamycin A) 與發利列(valifenalate)。 (10) 脂質與膜合成抑制劑,例如:聯苯、氣唑内 (chlozolinate)、地茂散(chloroneb)、大克爛(dicloran)、護粒 松(edifenphos)、依得利(etridiazole)、蛾卡(iodocarb)、丙基 喜樂松(iprobenfos)、亞賜普醇烷(iSOpr〇thiolane)、普莫卡 (propamocarb)、普莫卡鹽酸鹽、硫菌威(pr〇thiocarb)、白粉 松(pyrazophos)、五氣硝苯(quintozene)、四氯硝苯(tecnazene) 與特克斯-曱基(tolclofos-methyl) 〇 (11) 黑色素生合成抑制劑,例如:卡普醮胺(capropamide)、 地克赛(diclocymet)、芬散尼(fenoxanil)、太得(fthalide)、百 快隆(pyroquilon)與三賽唑(tricyclazole)。 (12) 核酸合成抑制劑’例如:本達樂(benalaxyl)、本達樂 -M(克拉利(kiralaxyl))、布滅莫(bupirimate)、克拉肯 (clozylacon)、地滅利(dimethirimol)、抑利莫(ethirimol)、伏 201136518 拉希(furalaxyl)、殺紋寧(hymexazole)、滅達樂(metalaxyl)、 滅達樂-Μ、歐弗斯(ofurace)、歐殺斯(oxadixyl)、噚啉酸 (oxolinic acid) 〇 (13) 訊號轉導抑制劑,例如:氯唾内(chlozolinate)、拌種洛 (fenpiclonil)、護汰寧(fludioxonil)、依普同(iprodione)、撲 滅寧(procymidone)、快諾芬(quinoxyfen)與免克寧 (vinclozolin) ° (14) 去偶合劑,例如:百蜗克(binapacryl)、白粉克(dinocap)、 富米松(ferimzone)、扶吉胺(fluazinam)與敵蜗普 (meptyldinocap) 0 (15) 其他化合物,例如:本塞吐(benthizole)、苯 口等畊(bethoxazin)、卡普黴素(capsimycin)、卡吩(carvone)、 喹啉曱硫胺酸鹽(chinomethionate)、克吩農(chlazafenon)、 庫發尼(cufraneb)、赛伏醯胺(cyflufenamid)、西莫尼 (cymoxanil)、赛芬胺(cyprosulfamide)、得滅(dazomet)、迪 布卡(debacarb)、二氯吩(dichlorophen)、地克美辛 (diclomezine)、地吩唑克(difenzoquat)、地吩唑克曱基硫酸 鹽、二苯基胺、抑克滅(ecomat)、吩普胺(fenpyrazamine)、 伏特夫(flumetover)、敗菌丹(fluoromid)、護硫醯胺 (flusulphamide)、噻菌淨(flutianil)、福賽得 (fosetyl-aluminium)、乙鱗 J弓(fosetyl-calcium)、乙填納 71 201136518 (fosetyl-sodium)、六氣苯、依麻黴素(irumamycin)、滅速卡 (methasulphocarb)、異硫氰酸甲酯、滅奇吩(metrafenone)、 米德黴素(mildiomycin)、納坦黴素(natamyCin)、二曱基二 硫代胺曱酸鎳、硝基太(nitrothal)-異丙基、歐奇農 (octhilinone)、歐賽保(oxamocarb)、歐芬汀(oxyfenthiin)、 五氯紛與其鹽類、驗丁滅盘(phenothrin)、磷酸與其鹽類、 霜黴威乙膦酸鹽(propamocarb-fosetylate)、普辛納 (propanosine-sodium)、普克奇(proquinazid)、0比 口各靈 (pyrrolenitrine)、美爾奎寧(tebufloquin)、特克爛 (tecloftalam)、特伏尼(tolnifanid)、三0坐氧(triazoxide)、三 氯酿胺(trichlamide)、奇利酿胺(zarilamide)、 l-(4-{4-[(5R)-5-(2,6-二氟苯基)-4,5-二氫-1,2-畤唑-3-基]-1,3-喧唾-2-基}派咬小基)-2-[5-曱基-3-(三氟曱基)-111-0比0坐-1-基]乙嗣、l-(4-{4-[(5S)-5-(2,6-二氣苯基)-4,5-二氮 -1,2-嘮唑-3-基]-1,3-噻唑-2-基}哌啶-1-基)-2-[5-甲基-3-(三 氟曱基HH-«比唑-1-基]乙酮、1-(4-{4-[5-(2,6-二氟苯基)-4,5-二氫-1,2-啐唑-3-基]-1,3-噻唑-2-基}哌啶-1-基)-2-[5-曱基 -3-(三I曱基)-1H-0比〇坐_1_基]乙酮、111-0米°坐-1-紱酸1-(4-曱 氧基苯氧基)-3,3-二甲基丁烧-2-基酯、2,3,5,6-四氣-4-(曱基 續醯基)吼啶、2,3-二丁基-6-氯噻吩并[2,3-d]嘧π定-4(3H)-_、2-[5 -曱基-3-(三氟曱基)-lH°比°坐-l-基]-l-(4-[4-[(5R)-5-本基-4,5-二氫-l,2-0号0坐-3-基]-l,3-α塞D坐-2-基}π辰^ϊ定_l-基)乙 酮、2-[5-曱基-3-(三氟曱基)-1Η·α比0坐-1-基]-l-(4-{4-[(5S)-5-本基·4,5-二氫-1,2-π^β坐-3-基]-1,3-嗟〇坐-2-基}派。定小基)乙 72 201136518 酮、2-[5-甲基-3-(三氟甲基)-1Η-°比唾_ι_基]苯基 -4,5_二氫-1,2-σ号嗤-3-基)-1,3-°塞唾-2-基]α底π定_1_基}乙酮、2_ 丁氧基-6-姨-3-丙基-4Η-色婦-4-酮、2-氣_5-[2-氣-1-(2,6-二 氟-4-甲氧基苯基)-4-曱基-111-0米°坐-5-基]η比咬、2-苯基苯紛 及其鹽類、3,4,5-三氣°比啶-2,6-二曱腈、3-[5-(4-氯苯基)-2,3-一曱基-1,2_十坐。定-3-基]〇比咬、3-氣-5-(4-氣苯基)-4-(2,6-二 氟本基)-6-甲基塔〇井、4-(4-氣苯基)-5-(2,6-二氟苯基)-3,6-二 甲基嗒畊、5-胺基-1,3,4-嗟二唑-2-硫醇、5j_N,-苯基以匕(丙 -2-块小基)嘆吩_2_亞硫叛醯肼、5·甲基-6-辛基[1,2,4]三唾并 U,5-a]嘧啶-7-胺、(2Z)-3-胺基_2_氰基_3_苯基丙_2_烯酸乙 酷、N-(4-氯苯甲基)-3-[3-曱氧基·4_(丙m基氧)苯基] 丙醯胺、N-[(4-氯苯基)(氰基)曱基]-3_[3_甲氧基_4_(丙_2_快 -1-基氧)苯基]丙醯胺、N-[(5-溴-3-氣η比咬-2-基)曱基]_2,4-二氣吡啶-3-曱醯胺、N-[l-(5-溴-3-氣吡啶-2-基)乙基]_2,4-二氯°比啶-3-曱醯胺、N-[l-(5-溴-3-氣吡啶-2-基)乙基]_2_氟 -4-碘吡啶·3_曱醯胺、Ν-{(Ε)-[(環丙基曱氧基)亞胺基][6_(二 氟曱氧基)-2,3-二氟苯基]曱基}-2-苯基乙醯胺、Ν-{(Ζ)-[(環 丙基曱氧基)亞胺基][6-(二氟曱氧基)_2,3-二氟苯基]甲 基苯基乙醯胺、Ν-曱基-2-(1-{[5-曱基-3·(三氟曱基)_1Η_ °比唾-1-基]乙醯基}α底咬_4_基)-Ν-(1,2,3,4·四氫萘-1-基)_ι,3_ 噻唑-4-甲醯胺、Ν-曱基-2-(1-{[5-曱基-3-(三氟曱基)_1Η_’Π比 唾-1-基]乙醯基}哌啶-4·基)-N-[(1R)-1,2,3,4-四氫萘小 基M,3-噻唑-4-曱醢胺、N-曱基-2-(l-{[5-曱基-3-(三氟曱 基)-1Η-吼唑-1-基]乙醯基}哌啶四氣 73 201136518 萘-1-基]-1,3_售哇_4_甲醯胺、{6傭卜甲基四嗤-5_ 基)(苯基)亞甲基]胺基}氧)甲基]対_2_基}胺甲酸戍醋、吩 畊-1-羧酸、喹啉_8_酚及喹啉_8_酚硫酸鹽(2 : 1}。 (16)其他化合物,例如:l曱基_3_(三說甲基)_N_[2l_(三氣甲 f )聯笨-2-基]-lH-n比唾-4-曱酿胺、N_(4,'氯聯苯_2_基)_3_(二 氟甲基)-1 -曱基-1H-吡唑_4_曱醯胺、N_(2,,4,_二氣聯苯_2_ 基)-3-(二氟曱基)_1_甲基-1H-吼唑-4-曱酿胺、3-(二氟甲 基)-卜甲基-N-[4’-(三氟曱基)聯苯_2•基]1H_吡唑_4_曱醯 胺、N-(2’,5’-二氟聯苯-2-基)-1_曱基_3_(三氟曱基)_1H_吡唑 -4-甲酿胺、3-(二氟甲基;)小甲基_Ν·[4,_(丙+炔小基)聯苯 -2-基ΗΗ-吼唑-4-甲醯胺、^氟-以二曱基_队[4,_(丙小炔 -1-基)聯苯-2-基]-1Η-吡唑·4-曱醯胺、2_氣_N_[4,-(丙_1_炔-1-基)聯苯-2-基]吡啶-3-曱醯胺、3_(二氟曱基)_ν_[4,_(3,3·二甲 基丁炔-1-基)聯笨-2-基]-1-甲基-1Η-吡唑-4-甲醯胺、 Ν-[4’-(3,3-二甲基丁·^快巧基)聯苯_2_基]_5_氟_u_二曱基 -lH-η比唾甲醯胺、3-(二氟曱基)_n-(4,-乙炔基聯苯-2-基)-卜甲基-1H-吡唑-4-曱醢胺、N-(4'-乙炔基聯苯-2-基)-·5-氟―1,3·二甲基-1Η-吡唑-4-曱醯胺、2-氯-Ν-(4,-乙炔基聯笨 -2-基)。比喷_3-曱醯胺、2-氣-Ν-[4'-(3,3-二甲基丁·1-炔-1-基) 聯苯-2-基]吡啶_3_甲醯胺、4_(二氟曱基)_2_甲基_Ν_[4,·(三 氟曱基)聯苯-2-基]·1,3-噻唑-5-曱醯胺、5-氟·Ν·[4,-(3-羥基 3甲基丁快-1-基)聯苯-2-基]-1,3-二甲基· 1Η-π比w坐-4-曱 醯胺、2-氣-Ν-[4,-(3-羥基_3_曱基丁_丨·炔_丨_基)聯苯_2_基]吡 74 201136518 啶曱醯胺、3-(二氟甲基)-N-[4,-(3-甲氧基甲基丁〇 -1-基)聯苯-2-基]-i_甲基·1Η_吡唾_4_甲醯胺、5一氣 、夫 甲氧基-3_甲基丁块·!基)聯苯_2基二甲基、 ,-4-曱酉藍胺、2'氣_Ν_[4·_(3_甲氧基_3-甲基丁小块^ : 苯-2-基]吡啶_3_甲醯胺、(5_溴_2_甲氧基_4_甲基吡二9 基)(2,3,4-三甲氧基_6-曱基苯基)甲酮及ν-[2_(4_{[3_(4_^· 基}丙_2_炔]_基]氧}_3_甲氧基苯基〕乙基]七 、本 纈胺醯胺。 土尹、醯基) 所有上述(1)至(16)類之混合對象若適當時,均可斑入 適鹼或酸類形成鹽,只要其官能基可行即可。 ^ σ 所有植物與植株部份均可根據本發明處理。此 瞭解植物係指所有植物及植物族群,> :需要及不需要^ =生植物或作物(包括天然作物)。作物可為得自依傳統植 月種法與最適化方法或湘生物技術與遺傳卫程法或 方法之組合所取得者,包括轉殖基因植物,包括 3 =保護或未受保護之植物栽培品種。亦咸瞭解,二 *部份意指植物之所有地上及地下部份與器官,如.# 葉、花與根,其實例可述及:闊葉 葉 ^、 ,果實、種子,及根、球莖與根莖。匕 好收穫之材料,與無性及有性繁殖材料’例如:插枝、球 1、根莖、槩枝與種子。 使用活性成份根據本發明處理植物與_部份之方法 係依傳統處理法直接處理或使化合物作用在 地或庫存空間,例如:浸泡、噴灑 二々兄 心 賀麗舔發、噴霧、撒播、 75 201136518 塗刷、注射、澆灑,若處理繁殖材料 亦可包覆一層或多層包衣。 尤,、處理種子時, 如上述,根據本發明可處理所有 較佳具體實施例中係處理野生植物品種盘植物=份植株。 或彼等由傳統生物育種法(如:交 码、植物载培品種’ 者,與其部份植株。另一(項較 遺傳工程(若適當時,可併⑽統方 ’係處理由 與植物栽培品種(基因改造生物),及殖基因植物 份」;:r::」或「部份植株二語「部 物栽培品種之植:本=處=品,使用中之植 育種法、誘變法或重組DNA 、培。。種意指經由傳統 性」)之植物。其可為生:型 較佳植物為彼等來自有用植物、 用為公共與私人領域之觀賞植物貝才物、草皮、常 林樹木包括用於生長木材、、,及森林樹木。森 製造之產品等之樹木。、、’’4、紙張及由樹木之一部份 料、於取得食物、飼 _:本==:處:之有用 植物包括例如:下 裸麥、燕麥、稻、玉米=,例如:小麥、大麥、 菜與飼料用甜菜;果實,彳/、间米,甜釆,例如:糖用甜 如:蘋果、梨、李、桃仁果、核果與軟果類,例 杏子、櫻桃與莓果類,例如:草 76 201136518 葛、刺莓、黑莓;豆類,例如:菜豆、爲豆、疏豆盘大豆; =作物’例如:油菜、齐菜、罌f、撖欖、葵花、、椰子、 麻油植物、可可豆與花生;瓜類,<列如:南瓜 (PumPkln/squash)、胡瓜與香瓜;纖維植物,例如:棉花、 與黃麻;柑橘類水果,例如:柳 =St!如:渡菜、葛苣、蘆筒、包心菜類、 楊备㈣力口馬龄薯與青椒;樟科(LaUraceae), ^、肉桂、樟腦或如:料、核桃、咖啡、祐子、 賞植物等植物,例如以卉年:】:、!:、乳膠植物與觀 列表並不代餘何關財4木、料木與針葉樹。此 下^㈣制適合❹本發性錄處理之標的 r i茄子、草皮、仁果、核果、軟果、玉米、小 夕二大麥、/月瓜、於草、攸藤植物、稻、穀類、梨、豆類、 大旦、油莱、㈣、#椒、香瓜、包心菜、馬鈐薯及韻果。 可依據本發明方法改良之樹木實例為:冷杉屬(Abies sp.)、桉屬(Euealyptus sp.)、雲杉屬(pieea sp )、松屬(ρί_ sp.)、七葉樹屬(A_lUS sp.)、懸鈴木屬(piat_ sp )、椴 屬(Tlha SP.)、槭屬(Acer SP.)、鐵杉屬(Tsuga sp.)、白堰屬 (Fraxinus sp.)、花楸屬(s〇rbus sp )、樺屬(⑽也 sp )、山榷 屬(Crataegus sp.)、榆屬(ulmus sp )、櫟屬⑹狀化似sp )、櫸 屬(Fagus sp.)、柳屬(Salix sp )、自楊屬(p〇puius sp ) 可依據本發明方法改良之較佳樹木實例為 :下列七葉 樹(Aesculus)屬種樹木:歐洲七葉樹(A hipp〇castanum)、a 77 201136518 pariflora、紅色七葉樹(a. carnea);下列懸鈴木(Platanus)屬 種:P. aceriflora、美國梧桐(p. occidentals)、P. racemosa;下 列雲杉(Picea)屬種樹木:歐洲雲杉(p. abies);下列松(Pirms) 屬種樹木:輻射松(p. radiate)、西黃松(P. ponderosa)、扭葉 松(P. contorta)、歐洲赤松(P. sylvestris)、濕地松(P. elliottii)、西部白松(p. montecola)、美國白皮松(P. albicaulis)、赤松(p. resinosa)、長葉松(P. palustris)、火炬松 (P. taeda)、柔松(P. flexilis)、黑材松(Ρ· jeffregi)、北美短葉 松(R baksiana)、北美喬松(p. strobes);下列按(Eucalyptus) 屬種樹木:玫瑰桉(E. grandis)、藍桉(E. globulus)、E. camadentis、亮果桉(E. nitens)、斜葉桉(E. obliqua)、王桉(E. regnans)、弹丸桉(E. pilularus)。 可依據本發明方法改良之特別佳樹木實例為;下列松 (Pmus)屬種樹木:輻射松(P. radiate)、西黃松(p p〇nder〇sa)、 扭葉松(R contorta)、歐洲赤松(p Syivestris)、北美喬松(p strobes);下列桉(Eucalyptus)屬種樹木:玫瑰桉(E grandis)、 藍桉(E. globulus)及 E. camadentis。 可依據本發明方法改良之極特別佳樹木實例為:七葉 樹、懸鈴木科(Platanaceae)、椴樹、楓樹。 本發明亦可應用在任何草坪,包括冷季型草坪及暖季 型草坪。 依植物品種或植物栽培品種、其位置與生長條件(土 壤、氣候、營養生長期、肥料)而異,根據本發明處理法亦 可能產生超過加成性(「促效性」)效果。因此,可能超過 78 201136518 強根據降率與/或擴大活性範圍與/或加 長、提高料質與組合物之活性、改善植物生 或土壤鹽含二=„性、提高對乾旱或對水含量 值、高所收成產品之品質與/或提高營養ί 性與/或提高所收成產品之可加工性。 (由遺傳工Λ明處歡較佳轉殖基馳物或植物栽培品種 者他細杨基目妓過財,接受賦與 物生長;^之遺傳物質之植物。此等特性實例為改善植 含量或土 溫或低溫之耐受性、提高對乾旱或對水 速成ί = 受性、改翔花率、簡化收成、加 養ί值、^收獲量、提高所收成產品之品質與/或提高營 存安枝與/或提高所收成產品之可加工 愈微:物ίϊΓ:!調之此等特性實例為植物對抗動物害蟲 ϊ 更佳防禦性,如:對抗昆蟲、蜗、植 ’二'生真囷、細㈣/或病毒,亦提高植物對某些除草活 、知之耐%性。此等(轉殖基因)植物可述及之實例為重要 作物,如:穀類(小麥、稻)、玉米、大豆、馬龄著、甜菜、 «、豌豆及其他蔬菜品種、棉花、㈣、油菜與果實植 物(蘋果、梨、掛橘與葡萄),特別著重於玉米、大豆、馬鈐 薯、棉花、㈣與油菜。所特別_之特性為·植株内7 所形成毒素,特定言之由來自蘇雲金芽胞桿菌(Baci細 thuringiensis)之遺傳物質(例如:基因❻从⑻、❻认⑻、 CrylA⑷、CryllA、CryllU、CryIIIB2、Cry9c、以施、 79 201136518
Cry3Bb與CrylF及其組合)於植株内所形成之毒素(下文中 稱為「Bt植物」)提尚對抗艮蟲、缺I蛛類、線蟲、及蜗牛斑 蛞蝓之防禦性。亦特別強調之特性為利用後天取得之全株 抗性(SAR)、系統素(systemin)、植物抗毒素(phytoalexins)、 誘發素(elicitors)與抗性基因’及相應表現之蛋白質與毒 素’提高對抗真菌、細菌與病毒之防禦性。其他特別強調 之特性為k南植物對某些除卓活性成份,例如:σ米。坐琳酮 類、磺醯脲類、草甘膦(glyphosate)或草銨膦(phosphinotricin) 之耐受性(例如:「PAT」基因)。此等賦與所需特性之基因 亦可相互組合進入轉殖基因植物中。「Bt植物」實例可述及 以下列商品名稱出售之玉米品種、棉花品種、大豆品種與 馬铃著品種· YIELD GARD®(例如:玉米、棉花、大豆)、 KnockOut®(例如:玉米)、StarLink®(例如:玉米)、 Bollgard®(棉花)、Nucotn®(棉花)與 NewLeaf®(馬鈴薯)。 除草劑耐受性植物實例可述及以下列商品名稱出售之玉米 品種、棉花品種與大豆品種:Roundup Ready®(耐受草甘 膦’例如:玉米、棉花、大豆)、Liberty Link®(财受草錢膦 (phosphinotricin),例如:油菜)、IMI®(耐受咪唑啉酮類) 與STS®(耐受績酿脲類,例如:玉米)。可述及之除草劑抗 性植物(依傳統育種法育種而耐受除草劑之植物)包括以下 列商品名稱出售之品種:Clearfield®(例如:玉米)。當然, 此等說明亦適用於已具有此等遺傳特性或仍待發展出此等 遺傳特性’而將於未來發展與/或上市之植物栽培品種。 上述植物可依特別有利之方式,根據本發明,使用根 201136518 據本發明通式(i)化合物及/或活性成份混合物處理 。上述活 性成份或混合物所提及之較佳範圍亦適用於處理此等植 物。特別強調使用本文中明確說明之化合物或混合物處理 植物。 此外,本發明化合物可用於控制許多種不同害蟲,包 括例如:有害之吸食性昆蟲、叮咬性昆蟲及其他成為植物 寄生蟲之害蟲、庫存材料之害蟲、破壞工業原料之害蟲、 及衛生方面之害蟲,包括在動物健康方面之害蟲,及其控 制法,例如:其減少及根除法。因此本發明亦包括一種控 制害蟲之方法。 在動物衛生方面(亦即獸醫學),根據本發明活性成份可 活性對抗動物寄生蟲,尤指體外寄生蟲或體内寄生蟲。術 語「體内寄生蟲」尤其包括蠕蟲,如:絛蟲、線蟲或吸蟲, 及原生蟲,如:球蟲。體外寄生蟲通常且較佳為節肢動物, 尤指昆蟲’如:螫蠅與舔蠅、寄生蠅幼蟲、蝨、毛蝨、鳥 蟲、跳蚤’等等,或作為殺壁益劑,如:碑類,例如:硬 蜱或軟蜱、或蟎類’如疥蟎、秋收恙蟎、鳥蟎,等等。 此等寄生蟲包括: 兹目(Anoplurada) ’ 例如:盲蟲屬(Haematopinus spp.)、長 顎蝨屬(Linognathusspp.)、蝨蟎屬(Pediculus spp.)、陰蝨屬 (Phtirus spp.)、管蝨屬(Solenopotes spp.);特定實例為:棘 顆蟲(Linognathus setosus)、狐顆蟲(Linognathus vituli)、綿 羊顆 1¾ (Linognathus ovillus)、卵形顎蟲(Linognathus oviformis)、足顎兹(Linognathus pedalis)、狹顎益 201136518 (Linognathus stenopsis)、大頭盲兹(Haematopinus asini macrocephalus)、闊胸血益(Haematopinus eurysternus)、豬 血蟲(Haematopinus suis)、人頭益(Pediculus humanus capitis)、人體益(Pediculus humanus corporis)、Phylloera vastatrix、陰盘(Phthirus pubis)、短鼻牛為(Solenopotes capillatus); 食毛目(Mallophagida)及純角亞目(Amblycerina)與細 角亞目(Ischnocerina),例如··毛鳥蟲屬(Trimenopon spp.)、 雞兹屬(Menopon spp.)、巨毛益屬(Trinoton spp.)、羽兹屬 (Bovicolaspp.)、嚼為(Werneckiella)屬、Lepikentron屬、食 蟲 it 屬(Damalina spp·)、獸鳥兹屬(Trichodectes spp.)、猶羽 蟲屬(Felicola spp.);特定實例為:牛羽兹(Bovicola bovis)、羊羽蟲i (Bovicola ovis)、紅環羽蟲(Bovicola limbata)、牛食蟲 it pamalina bovis)、犬食毛盘 (Trichodectes canis)、描烏蟲(Felicola subrostratus)、山羊 毛蟲(Bovicola caprae)、羊盘(Lepikentron ovis)、馬嚼蟲 (Werneckiella equi); 雙翅目(Diptera)及長角亞目(Nematocerina)與短角亞目 (Brachycerina),例如:伊蚊屬(Aedes spp.)、按蚊屬 (Anopheles spp.)、庫蚊屬(Culex spp.)、蚋蚊屬(Simulium SPP.)、真蚋屬(Eusimulium spp.)、白蛉屬(Phlebotomus spp.)、沙繩屬(Lutzomyia spp.)、蚊屬(Culicoides spp.)、斑 it 屬(Chrysops spp.)、蚋屬(Odagmia spp.)、維蚋屬 (Wilhelmia spp.)瘤 it 屬(Hybomitra spp.)、黃 it 屬(Atylotus 82 201136518 spp.)、虻屬(Tabanus spp.)、麻翅虻屬(Haematopota spp.)、 Philipomyia 屬、蜂虱屬(Braula spp.)、家绳屬(Musca spp.)、 齒股蠅屬(Hydrotaea spp.)、螫蠅屬(Stomoxys spp·)、血蠅屬 (Haematobia spp.)、莫蠅屬(Morellia spp.)、廄蜷屬(Fannia spp.)、舌蠅屬(Glossina spp.)、麗蠅屬(Calliphora spp.)、綠 繩屬(Lucilia spp.)、金蠅屬(Chrysomyia spp.)、肉繩屬 (Wohlfahrtia spp.)、麻蠅屬(Sarcophaga spp.)、狂蠅屬(Oestrus SPP.)、皮繩屬(Hypoderma spp.)、胃繩屬(Gasterophilus spp.)、蝨蠅屬(Hippobosca spp.)、蝨蠅屬(Lipoptena spp.)、 羊兹罐屬(Melophagus spp.)、鼻狂绳屬(Rhinoestrus spp.)、 大蚊屬(Tipula spp.);特定實例為:埃及斑蚊(Aedes aegypti)、白線斑蚊(Aedes albopictus)、東鄉伊蚊(Aedes taeniorhynchus)、甘比亞瘧蚊(Anopheles gambiae)、五斑按 蚊(Anopheles maculipennis)、紅頭麗繩(Calliphora 67比1:006卩11&13)、兩麻翅紀((:1^>^0201^卩11^&1丨5)、致倦庫紋 (Culex quinquefasciatus)、淡色庫蚊(Culex pipiens)、媒斑 蚊(Culex tarsalis)、黃腹廁罐(Fannia canicularis)、肉繩 (Sarcophaga carnaria)、厩螫繩(Stomoxys calcitrans)、沼澤 大蚊(Tipula paludosa)、綿羊赤銅綠繩(Lucilia cuprina)、絲 光綠繩(Lucilia sericata)、爬蚋(Simulium reptans)、靜食白 蛉(Phlebotomus papatasi)、長鬚白蛉(Phlebotomus longipalpis)、短蚋(Odagmia ornata)、馬維蚋(Wilhelmia equina)、紅頭厭蚋(Boophthora erythrocephala)、it (Tabanus bromius、Tabanus spodopterus)、牛虹:(Tabanus 83 201136518 atratus、Tabanus sudeticus)、瘤 it (Hybomitra ciurea)、斑 it (Chrysops caecutiens、Chrysops relictus)、 麻 it (Haematopota pluvialis)、義大利麻 it (Haematopota italica)、秋家蠅(Musca autumnalis)、家蠅(Musca domestica)、血蠅(Haematobia irritans irritans)、角繩 (Haematobia irritans exigua)、 血繩(Haematobia stimulans)、 家繩 (Hydrotaea irritans、Hydrotaea albipuncta)、金繩(Chrysomya chloropyga)、蛆症金繩 (Chrysomya bezziana)、羊狂繩(Oestrus ovis)、牛皮蠅 (Hypoderma bovis)、紋皮蠅(Hypoderma lineatum)、牛蠅 (Przhevalskiana silenus)、人膚繩(Dermatobia hominis)、、绵 羊兹繩(Melophagus ovinus)、盘蠅(Lipoptena capreoli ' Lipoptena cervi)、 兹繩 (Hippobosca variegata、Hippobosca equina)、腸胃罐(Gasterophilus intestinalis)、赤尾胃繩(Gasterophilus haemorroidalis)、小 胃 ±1 (Gasterophilus inermis)、鼻胃繩(Gasterophilus nasalis)、黑角胃蠅(Gasterophilus nigricornis)、獸胃蠅 (Gasterophilus pecorum)、蜜蜂兹(Braulacoeca); 蚤目(Siphonapterida),例如:蚤屬(Pulex spp.)、梅頭 蚤屬(Ctenocephalides spp.)、潛蚤屬(Tunga spp.)、鼠蚤屬 (Xenopsylla spp.)、角葉蚤屬(Ceratophyllus spp.);特定實例為:狗樹頭蚤(Ctenocephalides canis)、描 梅頭蚤(Ctenocephalides felis)、致癯蚤(Pulex irritans)、穿 皮潛蚤(Tunga penetrans)、印鼠客蚤(Xenopsylla cheopis); 84 201136518 異翅目(Heteropterida),例如:臭蟲屬(Cimex spp.)、錐 蝽屬(Triatoma spp.)、紅腹獵蝽屬(Rhodnius spp.)、金圓蜂 M, (Panstrongylus spp.); 蜚蠊目(Blattaria),例如:東方斐蠊(Blatta orientalis)、 美洲大蠊(Periplaneta americana)、德國小蠊(Blattella germanica)、帶蠊屬(Supellaspp·)(例如:長鬚帶蠊(Suppella longipalpa); 蜱蟲(Acari)之亞目(粉蟲目(Acarina))及後氣亞目 (Metastigmata)與中氣亞目(Mesostigmata),例如:銳緣蜱屬 (Argas spp.)、純緣蜱屬(Ornithodorus spp.)、殘緣蜱屬 (Otobius spp.)、硬蜱屬(Ixodes spp.)、花蜱屬(Amblyomma spp.)、牛蜱屬(Rhipicephalus(Boophilus) spp.)、革碑屬 (Dermacentor spp.)、血蜱屬(Haemophysalis spp.)、璃眼蜱屬 (Hyalomma spp.)、扇頭蜱屬(Rhipicephalus spp.)(多重寄主 蜱之原始屬種)、禽蜗屬(Ornithonyssus spp.)、肺刺蜗屬 (Pneumonyssus spp.)、耳蜗屬(Raillietia spp.)、肺刺蜗屬 (Pneumonyssus spp.)、胸孔蜗屬(Sternostomaspp.)、瓦蜗屬 (Varroa spp.)、蜗屬(Acarapis spp.);特定實例為:波斯銳緣 蜱(Argas persicus)、鵠壁兹(Argas reflexus)、非洲純緣碑 (Ornithodorus moubata)、耳壁蟲(Otobiusmegnini)、微小牛 蜱(Rhipicephalus(Boophilus) microplus)、血紅扇頭蜱 (Rhipicephalus(Boophilus) decoloratus)、具環牛蜱 (Rhipicephalus(Boophilus) annulatus)、 方頭蜱 (Rhipicephalus(Boophilus) calceratus)、小亞璃眼碑 85 201136518 (Hyalomma anatolicum)、埃及璃眼蜱(Hyalomma aegypticum)、邊緣璃目艮蜱(Hyalomma marginatum)、長蝝璃 眼蜱(Hyalomma transiens)、紅腳扁兹(Rhipicephalus evertsi)、蓖麻豆兹(Ixodes ricinus)、六角形硬蜱(Ixodes hexagonus)、犬硬蜱(Ixodes canisuga)、多毛硬碑(Ixodes pilosus)、淺紅硬碑(Ixodes rubicundus)、黑腳硬蜱(Ixodes scapularis)、全環硬蜱(Ixodes holocyclus)、嗜群 jk 蜱 (Haemaphysalis concinna)、刻點血蜱(Haemaphysalis punctata)、 血碑 (Haemaphysalis cinnabarina、 Haemaphysalis otophila)、犬血蜱(Haemaphysalis leachi)、 長角血碑(Haemaphysalis longicorni)、邊緣革碑 (Dermacentor marginatus)、網紋革碑(Dermacentor reticulatus)、革蜱(Dermacentor pictus)、冬季革蜱 (Dermacentor albipictus)、安氏革蜱(Dermacentor andersoni)、變異革蜱(Dermacentor variabilis)、璃眼蜱 (Hyalomma mauritanicum)、血紅扇頭蜱(Rhipicephalus sanguineus)、囊形扇頭碑(Rhipicephalus bursa)、鐮形扇頭 碑(Rhipicephalus appendiculatus)、犬扇頭蜱(Rhipicephalus capensis)、圖蘭扇頭碑(Rhipicephalus turanicus)、贊比西 河扇頭蜱(Rhipicephalus zambeziensis)、美洲鈍眼蜱 (Amblyomma americanum)、彩飾純眼蜱(Amblyomma variegatum)、斑點純目艮蜱(Amblyomma maculatum)、希伯 來鈍眼蜱(Amblyomma hebraeum)、卡延鈍眼蜱 (Amblyomma cajennense)、雞皮刺蜗(Dermanyssus 86 201136518 gallinae)、囊禽刺蜗(Omithonyssus bursa)、林禽刺蜗 (Ornithonyssus sylviarum)、雅氏瓦蜗(Varroajacobsoni); 光芒轰亞目(Actinedida)(前氣亞目)(Prostigmata))與粉 蜗亞目(Acaridida)(無氣亞目)(Astigmata),例如:蜂蜗屬 (Acarapis spp.)、姬蟄蜗屬(Cheyletiella spp.)、禽螫瞒屬 (Ornithocheyletia spp.)、肉蜗屬(Myobia spp.)、綿羊齋蜗 (Psorergates spp.)、脂虫茜屬(Demodex spp.)、恙蜗屬 (Trombicula spp.)、螫蜗屬(Listrophorus spp.)、粉蜗·屬 (Acarus spp.)、食酿瞒屬(Tyrophagus spp.)、嗜木蜗屬 (Caloglyphus spp.)、Hypodectes 屬、翅蜗屬(Pterolichus spp.)、癯·瞒屬(Psoroptes spp.)、皮蜗屬(Chorioptes spp.)、耳 虫茜屬(Otodectes spp.)、疮蜗屬(Sarcoptes spp.)、耳蜗屬 (Notoedres spp.)、鳥济蜗屬(Knemidocoptes spp.)、雞蜗屬 (Cytodites spp.)、雞雛瞒屬(Lamimosioptes spp.);特定實例為:犬恙蜗(Cheyletiella yasguri)、I苗恙蜗 (Cheyletiella blakei)、犬螺形瞒(Demodex canis)、牛螺形 蜗(Demodex bovis)、羊螺形蜗(Demodex ovis)、山羊蠕形 蜗(Demodex caprae)、馬螺形蜗(Demodex equi、Demodex caballi)、豬螺形蜗(Demodex suis)、秋收恙蜗 (Neotrombicula autumnalis)、 恙 蜗(Neotrombicula desaleri)、恙瞒(Neoschi5ngastia xerothermobia)、紅恙蜗 (Trombicula akamushi)、耳挤蟲(Otodectes cynotis)、小穿 孔济癣蟲(Notoedres cati)、犬療瞒(Sarcoptis canis)、牛齋 蜗(Sarcoptes bovis)、羊療蜗(Sarcoptes ovis)、山羊齋虫茜 87 201136518 (Sarcoptes rupicaprae(=S. caprae))、馬挤瞒(Sarcoptes equi)、緒疥蜗(Sarcoptes suis)、綿羊疼蜗(Psoroptes ovis)、 兔耳癯·蜗(Psoroptes cuniculi)、馬癯蜗(Psoroptes equi)、牛 挤癬(Chorioptes bovis)、羊癢蜗(Psoergates ovis)、鼻小蜗 (Pneumonyssoidic mange)、犬鼻蟎(Pneumonyssoides caninum)、武氏蜂盾蜗(Acarapis woodi)。 本發明活性成份亦適合控制侵害動物之節肢動物、場 蟲及原生蟲。該等動物包括農業畜牧動物,例如:牛、綿 羊、山羊、馬、豬、驢、路轮、水牛、兔子、雞、火雞、 鴨、鵝、飼養魚類與蜜蜂。該等動物亦包括畜養動物’亦 稱為寵物動物,例如:狗、貓、鳥籠内的鳥與水族箱内的 魚,及實驗動物,例如:倉鼠、天竺鼠、大鼠及小白鼠。 藉由控制此等節肢動物、魅與/或原蟲應可降低宿主 動物之死亡率及改善其生產力(指肉品、乳品、毛、皮、 蜂蜜,料)及㈣,_可_铺本發明活性成到 更經濟及更簡單之動物管理。 例如需要預防或干擾寄生蟲吸食宿主之血液(若可、 時)。此外’控制寄生蟲有助於防止傳染病原散播。订 本文在動物健康領域中所採用術語「控制」係指 性成份可使絲此料生蟲4物巾該寄生蟲之發古 效降低至無害程度。更明確言之,本文所採用「控= 指該活性成份可有效殺死該寄生&,抑= 繁殖。 、 通常’當⑽處鶴物時,可直接施用根據本發明活 88 201136518 性成份。較佳為呈醫筚細 二:二二其= 知方式使用投ί)動面’該活性成份係依下列已 飲劑、灌藥、二 式投藥,例如··注射(脱内、古下丸樂、傲食與塞劑,非經腸 植入式,鼻内投藥,緩m靜脈内、腹膜内,等等), 喷麗、洗灑及轉、、=樂之形式’例如:浸或泡、 之模塑物品如:項圈:t撒:’及藉助於含活性化合物 考隻变斗掛、尾掛、腳帶、韁繩、標識裝 壓嘴灑器中施用精;適合於氣霧劑或非加 噴灑器。 乃配物,例如1浦_器及氣霧式 、^•用於牲畜《禽、家庭寵物,等等時’本發明活性 成伤可呈调配物使用(例如:粉劑、可濕性粉劑[「wp」]、 乳液、乳化濃縮劑[「EC」]、流動性組合*、均質溶液及 懸斤濃縮劑[「S C」])’其中活性成份(直接使用或稀釋後使 用(例如:稀釋100至1_〇倍))含量為1至80重量%,或 其可作為化學浴使用。 若用於動物健康領域時,本發明活性成份可與合適之 増效劑或其他活性成份組合使用,例如:殺壁蝨劑、殺昆 蟲劑、驅蟲劑、抗原生蟲劑。 此外’發現根據本發明化合物對破壞工業原料之昆蟲 具有強力殺昆蟲作用,可對抗破壞工業原料之昆蟲。因此, 本發明亦有關以本發明化合物於保護工業原料,對抗昆蟲 89 201136518 之肆虐或破壞上之用途。 可述及下列昆蟲’其供範例且為較佳範例,但未加以 限制: 曱蟲類如:家天牛(Hylotrupes bajulus)、多毛天牛 (Chlorophorus pilosis)、傢俱竊蠹(Anobium punctatum)、紅 毛竊蠹(Xestobium rufovillosum)、Ptilinus pecticornis、 Dendrobium pertinex、粉竊蠹(Ernobius mollis)、Priobium carpini、歐洲竹粉蠹(Lyctus brunneus)、非洲粉螽(Lyctus africanus)、平頸粉橐(Lyctus planicollis)、桴粉蠹(Lyctus linearis)、軟毛粉蠢(Lyctus pubescens)、扁腿粉蠹 (Trogoxylon aequale)、鱗毛粉蠹(Minthes rugicollis)、小蠹 屬(Xyleborusspec.)、Tryptodendron 屬、咖啡黑長蠹(Apate monachus)、獬長蠹(Bostrychus capucins)、歐洲竹異長蠹 (Heterobostrychus brunneus)、長蠹屬(Sinoxylon spec.)、竹 長蠢(Dinoderus minutus)。 膜翅目(Hymenopterans)如:鋼青樹蜂(Sirex juvencus)、大樹蜂(Urocerus gigas)、泰格大樹蜂(Urocerus gigas taignus)、Urocerus augur ° 白蟻類如:木白蟻(Kalotermes flavicollis)、短白蟻 (Cryptotermes brevis)、灰點異白蟻(Heterotermes indicola)、 黃胸犀白蟻(Reticulitermes flavipes)、山道犀白議 (Reticulitermes santonensis)、避光犀白蟻(Reticulitermes lucifugus)、澳洲白蟻(Mastotermes darwiniensis)、内華達古 白蟻(Zootermopsis nevadensis)、家白蟻(Coptotermes 201136518 formosanus) ° 衣魚通如.西洋衣魚(Lepismasaccliarina)。 咸瞭解,本文所指之工業原料為無生命材料如交 為塑膠、膠黏劑、#水1氏張及紙板、皮革、木材盘加工 木製品及塗料組合物。 現成可用之組合物若適當時,可包括其他殺尾蟲劑, 且若適當時,可使用一種或多種殺真菌劑。 根據本發明化合物同樣可用於與鹽水或有鹽味的水接 觸之需要保護之物品,尤指:船體、隔板、編網、建築物、 繫船設備及訊號系統,防止汗塞。 此外,本發明化合物可單獨使用或與其他活性成份組 合’作為抗汙塞劑使用。 活性成份亦適用於在居家、衛生及保護庫存產品中控 制動物害蟲,尤指昆蟲、蜘蛛與蟎類等常出現在封閉空間 之害蟲,例如:公寓、廠房、辦公室、車廂,等等。其可 單獨使用或與其他在豕庭用殺昆蟲劑產品中控制此等害蟲 之活性成份與佐劑組合使用。其可活性對抗敏感性及抗性 品種,並對抗所有發展階段。此等害蟲包括: 鐵目(Scorpionidea) ’ 例如:甜徵(Buthus occitanus)。 碑虫茜目(Acarina) ’例如:波斯銳緣碑(Argaspersicus)、 翅緣銳緣碑(Argas reflexus)、苔瞒屬(Bryobia ssp.)、雞皮刺 蟎(Dermanyssus gallinae)、家禽甜食蟎(Glyciphagus (1〇1^5如旧)、非洲鈍緣蜱(〇11^110(1〇1*1^1110仙&〇、血紅扇頭 碑(Rhipicephalus sanguineus)、恙瞒(Trombicula 201136518 alfreddugesi)、秋收中性恙蜗(Neutrombicula autunmalis)、 歐洲家刺皮瞒(Dermatophagoides pteronissimus)、美洲家刺 皮蜗(Dermatophagoides forinae) ° 知蛛目(Araneae),例如:鳥蛤虫知蛛(Aviculariidae)、圓 蛛(Araneidae) 〇 盲蛛目(Opiliones),例如:螫擬蠍(Pseudoscorpiones chelifer)、擬燦(Pseudoscorpiones cheiridium)、長崎盲蛛 (Opiliones phalangium)。 等足目(Isopoda),例如:海姐(Oniscus asellus)、球鼠 婦(Porcellio scaber)。 重足目(Diplopoda),例如:Blaniulus guttulatus、山爱 蟲屬(Polydesmus spp.)。 唇足目(Chilopoda),例如:地娱虫公屬(Geophilus spp.)。 總尾目(Zygentoma),例如:衣魚屬(Ctenolepisma spp.)、西洋衣魚(Lepisma saccharina)、衣魚(Lepismodes inquilinus) 〇 蜚蠊目(Blattaria),例如:東方蜚碟(Blatta orientalis)、 德國蜚蠊(Blattella germanica)、蜚嫌(Blattella asahinai)、馬 得拉蜚蠊(Leucophaea maderae)、古巴蜚嫌屬(Panchlora spp.)、帕科蜚蠊屬(Parcoblatta spp.)、澳洲蜚嫌(Periplaneta australasiae)、美洲蜚蠊(Periplaneta americana)、褐色蜚蠊 (Periplaneta brunnea)、煙色蜚蠊(Periplaneta fuliginosa)、長 鬚蜚蠊(Supella longipalpa)。 跳躍亞目(Saltatoria),例如:家總蟀(Acheta 92 201136518 domesticus)。 革翅目(Dermaptera),例如:歐洲球螋(Forficula auricularia)。 等翅目(Isoptera),例如:木白蟻屬(Kalotermes spp.)、 犀白蠛屬(Reticulitermes spp.)。 儒蟲目(Psocoptera),例如:Lepinatus屬、書益屬 (Liposcelis spp.)。 鞘翅目(Coleoptera),例如:圓皮蠹屬(Anthrenus spp.)、 毛皮蠹屬(Attagenus spp.)、皮蠹屬(Dermestes spp.)、長頭榖 盜(Latheticus oryzae)、郭工蟲屬(Necrobia spp.)、蛛甲屬 (?如115 3卩口.)、谷蠹(尺1^0卩611;]1&(1〇11^11化&)、榖象(8如卩1^1115 granaries)、米象(Sitophilus oryzae)、玉米象(Sitophilus 雙翅目(Diptera),例如:埃及伊蚊(Aedes aegypti)、白 紋伊蚊(Aedes albopictus)、Aedes taeniorhynchus、按蚊屬 (Anopheles spp.)、紅頭麗繩(Calliphora erythrocephala)、雨 麻虻(Chrysozona pluvialis)、致倦庫蚊(Culex quinquefasciatus)、尖音庫蚊(Culex pipiens)、跗斑庫蚊(Culex tarsalis)、果蝇屬(Drosophila spp.)、黃腹廄繩(Fannia canicularis)、家繩(Musca domestica)、白蛉屬(Phlebotomus spp.)、食肉麻 4¾ (Sarcophaga carnaria)、蚋屬(Simulium spp·)、螫蠅屬($t〇moxys calcitrans)、沼澤大蚊(Tipula paludosa) ° 鱗翅目(Lepidoptera),例如:小蠟螟(Achroiagrisella)、 93 201136518 大蠛頌(Galleria mellonella)、印度穀螺(Plodia interputictella)、木塞穀蛾(Tinea cloacella)、網衣蛾(Tinea 卩6111〇1^11&)、袋衣蛾(1'0^〇1&1^561以11&)。 蚤目(Siphonaptera),例如:狗櫛頭蚤(Ctenocephalides canis)、I苗櫛頭蚤(Ctenocephalides felis)、人蚤(Pulex irritans)、穿皮潛蚤(Tunga penetrans)、東方鼠蚤(Xenopsylla cheopis)。 膜翅目(Hymenoptera),例如:木工蟻(Camponotus herculeanus)、黑草蠘(Lasiusfuliginosus)、普通黑蟻(Lasius niger)、Lasius umbratus、小家蟻(Monomorium pharaonis)、 Paravespula 屬、草地蟻(Tetramoriumcaespitum)。 兹目(Anoplura),例如:頭盘(Pediculus humanus capitis)、體兹(Pediculus humanus corporis)、瘿棉财屬 (Pemphigus spp.)、葡萄根瘤財(Phylloera vastratrix)、陰蟲 (Phthirus pubis)。 異翅目(Heteroptera),例如:熱帶臭蟲(Cimex hemipterus)、溫帶臭蟲(Cimex lectularius)、長紅獵蝽 (Rhodnius prolixus)、騷擾錐蝽(Triatoma infestans)。 在家庭用殺昆蟲劑之領域中,其可單獨使用或組合其 他合適活性成份使用,如:磷酸酯類、胺曱酸酯類、擬除 蟲菊酯類、類新菸鹼類、生長調節劑或來自其他已知殺昆 蟲劑類之活性成份。 其可呈氣霧劑、無壓力喷灑產品,例如:泵壓及霧化 喷灑器、自動喷霧系統、霧化器、發泡物、凝膠、使用由 94 201136518 纖維素或聚合物製成之蒸發片之蒸發器產品、液體蒸發 器、凝膠及膜式蒸發器、螺漿驅動式蒸發器、無能源或被 動式蒸發系統、捕蟲紙、捕蟲袋及捕蟲膠,呈粒狀或細粉, 用於撒播式誘餌或用於誘餌台等形式使用。 製法及中間物之說明 本發明亦有關一種製備通式(I)化合物之方法
其中(^1至(^8、111至116、入、又、丫、¥、111及11分另|] 如上述定義, 其中 a)由通式(III)胺類
(ill) 與通式(Π)羧酸或羰基鹵化物反應,
95 (II) 201136518 其中L為鹵素或羥基, 得到通式(I)化合物,其中W為〇(氧原子),及 b)可視需要由通式(I)化合物,其中W為0(氧原子)隨後再 與硫續酸化劑反應,得到通式(I)化合物,其中w為S(硫原 子)。 本發明亦有關通式(I)中V為R4,R4為氫之化合物,及 其中R5為氫之化合物’及其中W為Ο之化合物。此等化 合物相當於下示化學式反應流程3中之通式(1-3)化合物。 本發明亦有關另一種製備本發明通式(1 -3)化合物之較 佳製法,其示於化學式反應流程3 ’其中 a)由通式(III)胺類
(ΠΙ) 與通式(V)丙烯酸衍生物反應’
得到通式(VI)_^類’ 96 201136518
b)隨後由通式(VI)丙烯醯胺類與通式(νπ)鹵素化合物反應
其係於叙觸媒之存在下進行, 得到通式(1-3)化合物,及其中L為函素或經基,及其中l1 為氯、7臭破或二鼠曱石黃酸根。 本發明進一步亦有關通式(VI)化合物,其係通式(1_3) 化合物製法之中間物。較佳通式(VI)化合物為Ν· {2,22_三氟 -1-[3-(二氟甲基)笨基]乙基卜丙烯醯胺,其製法說明於製備 實例之合成實例2步驟1中。 此外例如本發明式⑴化合物及明確之本發明式(1_3)化 合物之製法說明於下列化學式反應流程中。亦可參考製備 實例。 化學式反應流裎1至6以一般方式說明當W = 〇時,如何 依據本發明製法製備本發明式(I)化合物。通式⑴中w=0之 化合物下文中稱為通式(1-1)化合物。本發明式⑴中霄=3之 化合物可與硫磺酸化劑(例如:勞森試劑(Lawesson,s 97 201136518 reagent)、硫化敍或五硫化二_)反應製得。 化學式反應流程7至10出示式II化合物之製法。 化學式反應流程11至21出示明確之通式I化合物之製 法。 下文化學式反應流程及其說明中,Q1至Q^R1至R6、A、 X、Y、V、m及η分另如上述定義,除非各化學式反應流程 中出現不同定義。 化學式反應流程1 (通式I化合物之製法):
本發明通式(M)化合物可依化學式反應流程1所示製 備,其中 L 為鹵素或經基, 其係由通式結構(III)胺類與通式結構(II)活化羧酸衍生物反 應。針對(Π) ’可先使用醯基氯(例如:L=氯),於鹼之存在 下’例如:三乙基胺或氫氧化鈉。其次,亦可使用羧酸 (L=OH),但使用偶合劑(例如:二環己基碳化二亞胺),及 添加劑,如:1-羥基笨并三吐[Chem. Ber. 1970. 788]。其亦 可使用偶合劑,如:1-乙基-3-(3-二甲基胺基丙基)碳化二 亞胺、1,1’-羰基-1H-咪唑及類似化合物。使用偶合劑進行 98 201136518 之製法可能均適合製備酯或醯胺鍵之製法(參見例如: Bodansky等人之”胜肽合成法(Peptide Synthesis)”,第2版, Wiley & Sons, New York,1976; Gross,Meienhofer之”胜肽: 分析法、合成法、生物學(The Peptide : Analysis,Synthesis, Biology)”(Academic Press, New York,1979)。此外,亦可使 用混合酸酐製備(I) [J. Am. Chem. Soc 1967, 5012]。此製法 中,可能使用不同氯曱酸酯,例如:氯曱酸異丁基酯、氯 曱酸異丙基酯。同樣可基於此目的使用二乙基乙醯氯、三 曱基乙醯氯,等等。 化學式反應流程2 (通式1-2化合物製法):
本發明(1-2)型化合物-如化學式反應流程2所示-之製法 亦可由本發明通式結構(1-1)化合物與通式結構(IV)之烷化 劑或醯化劑(例如:曱基碘),於合適鹼(例如:氫化鈉)之存 在下反應, 其中,式(1-1)、(IV)及(1-2)中, L1為氯、溴、碘、曱苯磺酸根或曱磺酸根,及 R3a為心-仏-烷基或CrC4-烷基羰基。 化學式反應流程3(通式1-3化合物製法) 99 201136518
式(i)化合物可依兩步驟製程製得,如化學式反應流程3 所示,其中式(VII)中, L1 為氯、溴、碘或三氟甲磺酸根。 在習知之製程中,由式(ΙΠ)胺類先與式(V)丙烯酸衍生 物反應,產生式(VI)丙烯醯胺類。該反應之合適反應條件相 當於針對化學式反應流程1中式(Π)羧酸衍生物與式(ΠΙ)胺 類之反應之反應條件。 式(VI)丙烯醯胺類隨後可與式(VII)鹵素化合物採用文 獻中之方法,於鈀催化之反應中反應,產生本發明式⑴化 合物。所使用之鈀觸媒可為例如:於三苯基膦之存在下之 乙酸le(參見例如:Synlett 2006, 18, 2969-2972)。 化學式反應流程4 (通式1-5及1-6化合物之製法) 100 201136518
式⑴化合物亦可依化學式反應流程4所示,由其他式⑴ 化合物之官能基轉化得到。 例如式(1-4)羧酸酯化合物(其可依化學式反應流程1或3 所示之方法合成)可先類似文獻中常見之方法,於鹼(例如: 氫氧化鋰)之存在下水解,產生式(1_5)羧酸(參見例如:J.
Am. Chem. Soc. 1986, 108, 4603)。 式(1-5)羧酸可再與式(χιιι)胺類反應,產生式屮6)羧醯 胺衍生物。該反應之可能反應條件已詳細說明於化學式反 應流程1中式(II)羧酸衍生物與式(III)胺類之反應中。 化學式反應流程5 (通式1_8、1-9化合物之製法)
(1-9) 101 201136518 另一個由其他式⑴化合物之官能基轉化成式⑴化合物 之實例示於化學式反應流程5。 例如式(1-7)腈(其可依化學式反應流程1或3之方法合成) 可先類似文獻中已知之方法還原,產生式(1-8)胺類。適用 之還原劑包括例如:於觸媒(例如:鈀/碳)存在下之氫(參 見例如:J. Am. Chem. Soc. 1928, 50, 3370)或氫化鋰鋁(參 見例如:Org, Reac. 1951,6, 469)。式(1-8)胺類可再與式 (XIV)羧酸衍生物反應,產生式(i_9)羧醯胺衍生物。此等反 應之可能反應條件已明確說明於化學式反應流程1中式(II) 羧酸衍生物與式(III)胺類之反應。 化學式反應流程6 (通式1-11、1-12化合物之製法):
另一個由其他式(I)化合物之官能基轉化成式(I)化合物 之實例示於化學式反應流程6。 式(1-10)硝基化合物(其可依化學式反應流程1或3指 示之方法合成)可先類似文獻中已知之方法還原’產生式 (1-11)胺類。此等還原法之合適製程特定言之為金屬媒介之 反應,例如:氣化錫(II)、鐵粉、辞粉及其類似化合物。使 102 201136518 用例如:氯化錫(II)之金屬媒介還原反應可採用Organic Syntheses Coll. Vol. (III),453 說明之方法進行。 式(1-11)胺類可再與式(XIV)羧酸衍生物反應,產生式 (1-12)叛醯胺衍生物。此等反應之可能反應條件已明確說明 於化學式反應流程1中式(II)羧酸衍生物與式(III)胺類之反 應。 化學式反應流程6a (通式1-13及1-14化合物之製法):
另一個由其他式(I)化合物之官能基轉化成式(I)化合物 之實例示於化學式反應流程6a。 式(1-7)氰基化合物(其可依化學式反應流程1或3指示 之方法合成)可先類似文獻中已知之方法,與經基胺反應, 產生式(1-13)化合物。 式(1-13)化合物可再與式(χιν)羧酸衍生物(例如:羰基 氣),於鹼(例如:吡啶)之存在下反應,產生式(I-14)l,3,4-呤 二吐衍生物。 化學式反應流程6b (通式1_15化合物之製法): 103 201136518
式(I -15) Z -肉桂醯胺衍生物可依化學式反應流程6 b所 示製得。 在—般已知方法中,由式(VII)化合物先與式(XXV)丙 炔酸’於鈀觸媒(如:雙(三苯基膦)-鈀二氯化物)及銅鹽 (如:碘化亞銅⑴)之存在下反應,產生式(χχΥΙ)炔酸(參考 文獻:W02006/002981)。式(III)胺類可再與式(XXVI)羧酸 衍生物反應,產生式(χχνΠ)羧醯胺衍生物。適合此等反應 之反應條件相當於化學式反應流程1中式(II)羧酸衍生物與 式(III)胺類之反應所明確說明之反應條件。該式(χχνΐΙ)化 合物可再與氫,於合適觸媒(例如:林達(Lindlar)觸媒)之存 在下選擇性反應,產生式(I-15)Z-肉桂醯胺(參見例如:
Journal of Organic Chemistry 2003, 68, 2913-2920) ° 化學式反應流程6c (通式1-17化合物之製法): 104 201136518
L1—R8a (R1、 (IVa)
通式(I-17)N-經取代之吲哚衍生物可依化學式反應流 程6c所示製得, 其中 R8a為氫以外之R8。 此方法中’由通式(1-16)吲哚(其可依化學式反應流程1 指示之方法合成)與通式(IVa)化合物於驗(例如:碳酸鉀)之 存在下反應0 通式(II)中L為OH之羧酸可自商品購得或自文獻中已 知’或可依文獻中已知方法合成。 例如式(Ila)肉桂酸衍生物之製法,
—A/
Sr6), 係例如:由一般已知之溴-或碘芳基化合物進行赫克(Heck) 反應’與1-丙烯酸衍生物於多種紀觸媒(例如:乙酸把)之 存在下反應(可摘錄例如:下列參考文獻:Russian j. 〇rg. Chem 1995, 31, 439-444; Synth. Commun 2003, 33, 361-365; Chinese J. Org. Chem. 2004, 24, 59-62;Synthesis 1997, 1997, 521)。亦可依相同方式使用習知之苯胺類,其先於重氮化 劑(例如:亞硝酸鈉)之存在下轉化成重氮鹽’然後再與1- 105 201136518 丙烯酸衍生物,於鈀觸媒(例如:乙酸鈀)之存在下反應(可 摘錄例如:下列參考文獻:Eur. J. Org. Chem. 1999, 1357-1366)。式(Ila)肉桂酸亦可由芳香醛與丙二酸反應製得 (可摘錄例如:下列參考文獻:Org. Synth. 1963, IV,731; Synth. Comm. 1998, 28 (20),3811-15)。 新穎之通式II羧酸衍生物(L=OH)可例如:依下列方法 製得。 化學式反應流程7 (通式Π-1化合物製法)
式(II-1)化合物可依化學式反應流程7所示製得’其中 alkyl 為(^-(1!4-炫基, L2 為氯、溴、碘或三氟曱磺酸根’及 L3 為Η或CrC4-烷基,其中兩個L3取代基亦可形成5- 或6-員環。 如化學式反應流程7所示,先由式(VII)化合物與式(XV) 二羥硼酸或二羥硼酸酯於鈀觸媒之存在下反應’產生式 (XVI)肉桂酸酯。所使用之催化性鈀化合物可為鈀(11)化合 106 201136518 物,例如:雙(三環己基膦)把(II)二氣化物。 式(XVI)羧酸酯係依習知方法,例如:使用氫氧化鈉 作為鹼進行鹼性水解,轉化成相應之式(II-2)肉桂酸,或可 在C-C偶合反應期間變化反應條件(例如:溫度或反應時 間),得到游離酸。 化學式反應流程8 (通式II-2化合物製法)
(XVill) Y1-A^H 驗 ase
式(II-2)化合物可依化學式反應流程8所示製得,其中 L4 為氟、氣或溴, Υ^Α1-!!為可視需要經取代之三唾、β比吐、四唾或η米嗤,其 帶有一個游離Ν-Η官能基,其中適用之取代基為A 或Y之一般定義中明確說明之基團。 此時,依類似方法,先由式(XVII)醛與式(XVIII)雜環, 可視需要於鹼之存在下反應,產生式(IXX)醛,其中有些係 已知者(參見WO 2008019760; Tetrahedron (2001),57(22), 4781-4785)。 式(IXX)醛隨後可再類似文獻中之方法,與丙二酸於氮 鹼(例如:哌啶)之存在下反應,脫除羧基,產生式(II-2)肉 桂酸(例如:Bioorganic & Medicinal Chemistry Letters (2008), 18(5), 1663-1667; Journal of the Indian Chemical 107 201136518
Society (2007),84(6),612-614; Journal of Chemical Research (2005),(6),364-365)。 式(lib)苯并呋喃羧酸
同樣可自商品購得或自文獻中已知,或可依文獻中已知方 法合成。其實例包括: 5- 氰基-1-苯并°夫°南-2-鼓酸,(Liebigs Annalen der Chemie 1982, 10. 1836 - 1869) 6- 氟-1-苯并呋喃-2-羧酸,(US005955495A) 6-氟-1-苯并呋喃-2-羧酸,(JP2002/201193) 6-氰基-1-苯并呋喃-2-羧酸,(W02003/064411) 6-(三氟曱基)-1_笨并呋喃_2_羧酸,(US005955495A) 5-氯-6-曱基-1-苯并呋喃_2_羧酸。(W02005/080336) 新穎之式(II-3)苯并呋喃羧酸可依化學式反應流程9所 示製得,其中 L5 為氯或溴, ALK 為C「C4-燒基。 化學式反應流程9 (通式π_3化合物製法) 108 201136518
此外’類似已知方法(參見例如:DE 10115408),先由 式(XX)經基駿與式(ΧΧΙ)鹵羧酸烷基酯(如:鹵乙酸乙酯), 於驗(例如:碳酸鉀)之存在下反應,產生式(χχπ)苯并呋喃 缓酸酿。該式(ΧχΗ)羧酸酯再依已知方法轉化,例如:使 用氮氧化鈉作為鹼進行鹼性水解,產生相應之式(ΙΙ-3)苯并 呋喃羧酸。 式(lie)吲哚羧酸
同樣可自商品購得或自文獻中已知,或可依文獻中已知方 法合成。其實例包括: 5-,基-1H-吲哚_2·羧酸(j 〇rg chem.,1953, 18, 345 - 357) 6_氣基-1H-°弓卜朵-2-羧酸(J· Med. Chem.,1997, 40. 2843 - 109 201136518 2857), 5- (曱基磺醯基)-1Η-吲哚-2-羧酸(W02001/077101), 5,6-二氟-1H-吲哚-2-羧酸(W02006/082400), 6- 氣-1H-吡咯并[3,2-c]吡啶-2-羧酸(W02004/104001)。 新穎之式(Π-4),哚羧酸可依化學式反應流程10所示製 得。 化學式反應流程1 〇 (通式Π-4化合物製法)
此時’類似已知方法(參見例如:价oorg·. Med. CTzew. L抓.2003,13, 4385-4388),先轉化式(χχιπ)苯胺形成式 (XXIV)碘苯胺,然後再與丙酮酸於乙酸鈀及鹼(例如:1,4_ 重氮雙環[2.2.2]辛烷DABC0)之存在下反應,產生式(n_4) 苯并呋喃羧酸酯。 同樣由通式結構(II)(L= _素)代表之羰基齒化物(更佳 為幾基氯化物)之製法可由幾·酸(l=oh)與鹵化劑(如:亞硫 臨氣、亞硫醯溴、填臨氣、草醯氯、三氯化磷,等等)反應 [Houben-Weyl,1952, vol. VIII,p.463 ff.]。 通式(III)經鹵烷基取代之胺類可自商品購得或自文獻 中已知,或可依文獻中已知方法合成。例如:可由芳基鹵 化物與羧酸鹵烷基酯於鎂之存在下進行格林納(Grignard) 110 201136518 反應。所形成之酮可再進行還原性胺化反應’產生相應之 胺類(DE-A-2723464)。2,2,2-三氟-1·(吡啶-4-基)乙胺可自商 品購得’及可類似Angew. Chem. 1998,110. 6, 880 - 881及J. Mol. Cat. B : Enzymatic 30 (2004) 61-68說明之方法合成。 新穎之通式(III)經鹵烷基取代之胺類可例如:採用下 列方法製得。 化學式反應流程10a (通式III-1化合物製法)
其中 L6 為-C1-C4·烧氧基或-N (CHO-O-CVO烷基。 新穎之式(III-1)化合物可依化學式反應流程l〇a所示 製得。此時可先由自商品購得或文獻中之式(IIXXX)化合物 與金屬化試劑(例如:鎮、格林納(Grignard)化合物、正丁 基鋰或第三丁基鋰)反應,產生有機金屬中間物,其隨後再 與式(IXXX)化合物反應,得到式(XXX)酮。其可類似常用 之已知方法進行還原性胺化反應,轉化成式(III-1)胺類。由 酮(XXX)例如:與羥基胺反應,可形成肟中間物,其經過 還原劑(例如:氫化鋰鋁)還原,形成式(III-1)胺類。 式(VII)(雜)芳基鹵化物係已知或可依原則上已知方法 製備(參見例如:WO-A-2009055077、EP-A-1445253、 EP-A-661258 ' US-A-6252090 ' Chemical & Pharmaceutical 111 201136518
Bulletin (1992),40(7),1789-92、Chemical & Pharmaceutical Bulletin (1994),42(4),913-16、Compt. rend. (1954),237 357)。 新穎之通式(VII)(雜)芳基鹵化物可例如:採用下列方 法製得。 化學式反應流程l〇b (通式VII-1化合物製法)
新穎之式(VII-1)化合物可依化學式反應流程l〇b所示 製備。此時可由自商品購得或文獻中之式(XXXI)羧酸與式 (XIII)胺類反應。此等反應之反應條件已明確說明於化學式 反應流程1中式(II)羧酸衍生物與式(III)胺類之反應中。 化學式反應流程10c (通式VII-2化合物製法)
如化學式反應流程10c中之詳細說明,可類似已知方 法’先由已知式(XXXII)腈衍生物與式(XXXIII)烷基-格林 納(Grignard)試劑反應,得到式(XXXIV)胺類。式(XXXIV) 胺類可再與式(XIV)羧酸衍生物反應,產生式(VII-1)羧醯胺 112 201136518 衍生物。此等反應之可此反應條件已明確說明於化學式反 應流程1中式(II)羧酸衍生物與式(III)胺類之反應中。 化學式反應流程10d (通式VII-3化合物製法)
如化學式反應流程1 〇d中之詳細說明,類似已知方 法,先由式(XXXV)腈衍生物與還原劑(例如:氩化裡銘) 反應,產生式(XXXVI)胺類。式(XXXVI)胺類可再與式(χιν) 羧酸衍生物反應,產生式(VII-3)羧醯胺衍生物。此等反應 之可能反應條件已明確說明於化學式反應流程1中式(II)羧 酸衍生物與式(III)胺類之反應中。 化學式反應流程l〇e (通式VII-4化合物製法)
如化學式反應流程10e之詳細說明,類似已知方法, 由式(XXXVII)鹵素衍生物與式(XXXVIII)受Boc保護之 胺,於驗(例如:氫化鈉)之存在下反應。隨後,再脫除保護 基,得到式(VII-4)二級胺類。 113 201136518 通式(II)中L為OH之羧酸可自商品購得或自文獻中已 知,或可採用文獻中之方法合成(化學式反應流程7至 10)。通式(II)中L為鹵素之羰基鹵化物之製法將於化學式 反應流程10之後說明。 式(IV)、(IVa)、(V)、(XIII)、(XIV)、(XV)、(XVII)、 (XVIII)、(XX)、(XXI)、(XXIII)、(XXV)、(IIXXX)、(XXX)、 (XXXI)、(XXXII)、(XXXIII)、(XXXVI)、(XXXVII)及 (XXXVIII)化合物為自文獻中已知或可自商品購得之物質。 通式1-1、1-2、1-4、1-7及1-10化合物可依據化學式反 應流程1製得,通式π-l可依據化學式反應流程7製得。 依據本發明製備新穎式(I)化合物之方法最好使用稀釋 劑進行。適合進行根據本發明製法之稀釋劑除了水以外, 尚可使用所有惰性溶劑。其實例包括:函烴類(例如:氣烴 類’如:四氯乙烯、四氣乙烷、二氯丙烷、二氣曱烷、二 氣丁烷、氣仿、四氣化碳、三氯乙烷、三氯乙烯、五氣乙 烷、二氟苯、1,2-二氣乙烷、氯苯、溴苯、二氣笨、氯曱苯、 三氯苯)、醇類(例如:甲醇、乙醇、異丙醇、丁醇)、醚類(例 如:乙基丙基醚、曱基第三丁基醚、正丁基醚、苯曱醚、 苯乙、環己基曱基醚、二曱基醚、乙醚、二丙基醚、二 異丙基醚、二正丁基醚、二異丁基醚、二異戊基醚、乙二 醇一甲基醚、四氫α夫喃、二氧雜環己炫、二氯二乙基醚及 環氧乙烷與/或氧化丙烯之聚醚)、胺類(例如:三曱基_、三 乙基-、三丙基-、三丁基胺、Ν_曱基嗎啉、吡啶及四亞曱基 二胺)、硝基烴類(例如:硝基曱烷、硝基乙烷、硝基丙烷、 114 201136518 罐基苯、氯石肖基苯、鄰-石肖基曱苯;腈類,如:乙腈、丙产、 丁腈、異了腈、苯基氰、間氯笨基氰)、四氫。塞吩二氧化^、 二甲亞砜、四亞甲基亞碾、二丙基亞砜、苯甲基甲基亞砜、 二異丁基亞颯、二丁基亞硬、二異戊基亞颯、硬類(例如. 二曱基砜、二乙基砜、二丙基砜、二丁基砜、二笨基砜、 二己基礙、甲基乙細、乙基丙純、乙基異丁基钱及五 亞甲基硪)、脂系、環脂系或芳香系煙類(例如:戊烧、己燒、 庚烧、辛烧、德及X·業級煙類),及包含沸點範圍二. 觀至謂。c之成份之「白精油」、對_聚伞花素、沸點範圍 在70°c至190°C之石油顧份、環己院、甲基環己烧、石_、 石油英、辛烧、苯、甲苯、氯苯、漠苯、石肖基笨、二甲笨、 酉旨類(例如:乙酸曱酉旨、乙賴、丁醋、異丁醋、碳酸二甲酉旨、 二丁醋、伸乙醋);醯胺類(例如:六亞甲基磷醯胺、甲醯胺、 N-曱基曱賴、N,N_二曱基甲_、邮_二丙基曱酿胺、 N,N-二丁基甲醯胺、N_甲基吡咯咬、N_甲基己内醯胺、以 二甲基_3,4,5,6_四氫-2(1办。密咬、辛基料賴、辛基己内 酉&胺、1,3-一曱基_2』米唾琳二酮、N_曱酿基派咬、 二甲醯基哌啡)及酮類(例如:丙酮、乙醯苯 、甲基乙基酮、 曱基丁基酮)。 咸了解’根據本發明製法亦可於上述溶劑混合物及稀 釋劑中進行。 當進行根據本發明製法時,反應溫度可在相當大範圍 内變化。通常’所採用之溫度在一3〇0(:至+ 15〇0(:之間,較佳 在一 10°C 至+ 1〇〇。(];之間。 115 201136518 根據本發明製法通常在標準壓力下進行。然而,根據 本發明製法亦可能在加壓或減壓下進行,通常在0.1巴至15 巴之絕對壓力下進行。 進行根據本發明製法時,起始物之用量通常為約等莫 耳量。然而,亦可過量使用其中一種成份。該反應通常在 合適之稀釋劑中,在反應佐劑之存在下,可視需要亦於保 護性氣壓(例如:氮氣、氬氣或氦氣)下進行,且通常在所需 溫度下攪拌反應混合物數小時。依一般方法進行操作(參見 製備實例)。 用於進行根據本發明製法之鹼性反應佐劑可能為所有 合適之酸結合劑。其實例包括:鹼土金屬或驗金屬化合物 (例如:鋰、鈉、鉀、鎂、鈣及鋇之氫氧化物、氫化物、氣 化物及碳酸鹽)、脒鹼類或胍鹼類(例如:7_甲基-1,5,'三氡 雜-雙環(4.4.〇)癸-5_烯(MTBD);重氮雙環(4.3.〇)壬埽 (DBN)、重氮雙環(2.2.2)辛烷(DABCO)、l,8-重氮雙環(5.4.0) 十一碳烯(DBU)、環己基四丁基胍(CyTBG)、環己基四曱基 胍(CyTMG)、Ν,Ν,Ν,Ν·四曱基-I,8-萘二胺、五曱基哌咬)及 胺類,尤指三級胺類(例如:三乙基胺、三曱基胺、三笨甲 基胺、三異丙基胺、三丁基胺、三環己基胺、三戊基胺、 三己基胺、Ν,Ν-二甲基苯胺、Ν,Ν-二曱基曱苯胺、ν ~ 甲基-對胺基°比0定、Ν-曱基比口各η定、甲基略咬、甲茂 咪唑、Ν-曱基吡唑、Ν-曱基嗎啉、Ν-曱基六亞甲基二胺、 吡啶、4-吡咯啶并吡啶、4-二曱基胺基吡啶、喹啉、〜甲〇比 啶、β-曱吡啶、嘧啶、吖啶、Ν,Ν,Ν,,Ν,-四亞曱基二胺、 116 201136518 N,N,N’,N’-四伸乙基二胺、喹啐啉、N-丙基二異丙基胺、 N-乙基-二異丙基胺、N,N’-二甲基環己基胺、2,6-二曱基吡 啶、2,4-二曱基吡啶或三乙基二胺)。 用於進行根據本發明製法之酸性反應佐劑可能為所有 礦物酸類(例如:氫鹵酸類,如:氫氟酸、鹽酸、氫溴酸或 氫蛾酸,及硫酸、填酸、亞墙酸、破酸)、路易士酸(Lewis acids)(例如:氯化鋁(III)、三氟化硼或其醚合物、氯化鈦 (V)、氯化錫(V)、及有機酸類(例如:曱酸、乙酸、丙酸、 丙二酸、乳酸、草酸、富馬酸、己二酸、硬脂酸、酒石酸、 油酸、曱烧磺酸、苯甲酸、苯石黃酸或對曱苯石黃酸。 例如:由化學式反應流程11 -21說明本發明明確之較 佳通式I化合物製法。 化學式反應流程11 :
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下列製法及應用κ例在未限制下說明本發明。 製備實例 下列實例中,RT指室溫,亦即20°C,且「1 eq」之表 示法指1當量。 合成實例1 (通式1-1及1-2化合物依據化學式反應流程1 及2之製法) 步驟1 : (2E)-3-(4-氰基苯基)-N-{2,2,2-三氟-1-[3-(三氣甲基)苯基】乙 基}丙烯醯胺(表1之化合物編號la-8)
先添加280.8 mg (1.15 mmol) 2,2-三氟(三氟甲基) 苯基]乙胺(自DE-A-2723464中已知)及128 6 mg 〇 27 mmol)三乙基胺至2 ml二氯曱烷中,添加含221 3 mg (1 15 124 201136518 mmo1) (2E)-3-(4-氰基苯基)丙烯醯氯之溶液(由(2E)-3-(4-氰 基苯基)丙烯酸與草醯氣反應合成)。反應溶液於室溫下攪拌 18小時後,以二氣甲烷稀釋,以水洗滌3次,經硫酸鈉脫水。 減壓蒸餾排除溶劑’及殘質與二異丙基醚攪拌。 產量:280 mg (理論值之59.4%)。 ]K NMR (400MHz, d6-DMSO) δ= 6.09 (m, 1Η), 6.95 (d, 1H), 7.6 (d, 1H), 7.7 (m, 1H), 7.75 (m, 3H), 7.85 (m, 2H), 7.89 (m, 1H), 7.99 (m, 1H), 9.42 (d, 1H). HPLC-MS : logP = 3.54;質量(m/z) : 399.0 (M+H)+. 步驟2 : (2E)-3_(4_氰基苯基)-N-甲基-N-{2,2,2·三氟-1-[3-(三氟曱基) 苯基】-乙基}丙烯醯胺(表1之化合物編號la-25)
先添加 120.0 mg (0.30 mmol) (2E)-3-(4-氰基苯 基)-N-{2,2,2·三氟-l-[3-(三氟曱基)-苯基]乙基}丙烯醯胺(來 自合成實例1,步驟1)至2 ml N,N-二曱基曱醯胺,於〇。(:下 與19.7 mg (0.45 mmol)氫化鈉(55%油分散液)混合。添加 64.1 mg (0.45 mmol)曱基碘後,混合物於室溫下攪拌is小 時。反應混合物經乙酸乙醋稀釋,以水洗務3次,經硫酸納 脫水。減壓蒸餾排除溶劑,殘質經製備性HPLC純化(溶劑= 水(A)+乙腈(B),梯度=40分鐘,自10%B至100%B, 流速=18 ml/min)。 125 201136518 產量:32 mg (理論值之25%)。 巾 NMR (400 MHz,dr 乙腈)δ= 3.00 (s,3H),6.75 (br. m, 1H), 7.20 (d, 1H), 7.6 - 7.8 (m, 9H). HPLC-MS : logP = 4.01;質量(m/z) : 413.0 (M+H)+. 其他類似合成實例1製得之通式(I)化合物列於表1及 合成實例2 (通式1-3、1-5及1-6化合物依據化學式反應流程3 及4之製法) 步驟1 N-{2,2,2-三氟-1-[3-(三氟曱基)苯基]乙基}丙稀醯胺
先共同添加20.0 g (82.2 mmol) 2,2-三氟-1-[3-(三氟甲 基)苯基]乙胺(參考文獻DE 2723464)與含7.80 g (98.7 mmol)吡啶至500 ml二氣曱烷中,於〇。(:滴加7.44 g (82.2 mmol)丙烯醯氯。再攪拌反應混合物4小時,同時回溫至室 溫。隨後’混合物經水重覆洗滌,有機相經硫酸鈉脫水, 及減壓蒸餾排除溶劑。產物未再進一步純化即用於步驟2。 產量:14.2 g (理論值之44.6%) ]H NMR (400 MHz, d6-DMSO)5= 5.77 (m, 1H), 6.12 (m, 1H), 6.20 (m,1H),6.42 (m,1H),7.70 (m,2H), 7.79 (m,1H),7.92 (m,1H),8.02 (s,1H),9.41 (d,1H). 126 201136518 HPLC-MS : logP = 2.75; ^ f-(m/z) : 298.0 (M+H)+. 步驟2 4-[(1£)-3-_基-3-({2,2,2-三氟小[3_(三氟甲基)苯基]乙基} 胺基)丙-1-烯-1-基】_2_(三氟甲基)苯甲酸
於氬氣下’先依序添加3 34 g(7.90mm〇1)N_{2,2,2i 氟-l-[3-(三氟甲基)苯基]乙基}_丙稀醯胺(來自實例2,步驟 1)及2.49 g (7.90 mmol) 4-峨-2-(三氟曱基)苯曱酸(可自商品 購得,CAS 註冊編號:954815-11-3)、0.206 g (7.90 mmol) 三苯基膦、88.4 mg (0.39 mmol)乙酸鈀(II)及 13.5 g (133 mmol)三乙基胺至67 ml Ν,Ν-二曱基甲醯胺中,反應混合 物於100°C下攪拌5小時。加水後,以乙酸乙酯萃取溶液, 有機相經飽和氣化鈉溶液洗滌3次,及經硫酸鈉脫水。減 壓蒸餾排除溶劑,殘質經矽膠使用乙酸乙酯層析。 產量:2.57 g (理論值之60%)。 'H NMR (400 MHz, d6-DMSO) δ= 6.10 (m, 1H), 6.93 (d, 1H), 7.6 (m, 1H), 7.69 (m, 1H), 7.75 (m, 2H), 7.85 (m, 1H), 7.95 (m, 1H), 7.99 (m, 1H), 9.38 (d, 1H). HPLC-MS : logP = 3.29;質量(m/z) : 486.0 (M+H)+. 類似合成實例2,步驟2說明之方法,亦得到下列通 式(1-5)化合物: 127 201136518 2-甲基-4_[(1Ε)-3-酮基-3-({2,2,2-三氟小[3-(三氟甲基)苯基】 乙基}胺基)丙-1-烯-1-基]苯曱酸 lU NMR (400 MHz, d6-DMSO)5= 2.55 (s, 3H), 6.09 (m, 1H), 6.89 (d, 1H), 7.6 (m, 1H), 7.50 (m, 3H), 7.7 - 7.9 (m, 3H), 8.00 (m,1H),9.34 (d, 1H). HPLC-MS : logP = 3.14;質量(m/z) : 431.1 (M+H)+. 2-氣-4-[(lE)-3-酮基-3-({2,2,2-三氟-l-【3-(三氟甲基)苯基】乙 基}胺基)丙-1-烯-1-基】苯曱酸 巾 NMR (400 MHz,d6-DMSO) δ= 6.09 (m,1H),6.90 (d,1H), 7.6 (m,1H),7.50 (m,1H),7.60 (m,1H),7.71 (m,1H),7.79 (m,1H),7.90 (m,1H), 8.00 (s,1H),9.37 (d,1H). HPLC-MS : logP = 3.10;質量(m/z) : 452.0 (M+H)+. 2-溴-4-[(lE)-3-酮基-3-({2,2,2-三氟-1·[3-(三氟甲基)苯基]乙 基}胺基)丙-1-烯-1-基]苯曱酸 lU NMR (400 MHz, d6-DMSO)5= 6.09 (m, 1H), 6.91 (d, 1H), 7.6 (m, 1H), 7.50 (d, 1H), 7.62 (m, 1H), 7.70 (m, 2H), 7.79 (m, 1H), 7.90 (m, 1H), 7.99 (m, 1H), 9.36 (d, 1H). HPLC-MS : logP = 3.15;質量(m/z) : 496.0 (M+H)+. 步驟3 N-(l-氟丙烷-2-基)-4-【(lE)-3-酮基-3-({2,2,2-三氟-l_[3-(三 氟甲基)苯基]-乙基}胺基)丙-1-烯-1-基】-2-(三氟甲基)苯甲 醯胺(表1之化合物編號la-75)
12S 201136518
取49 mg (1 eq,0.1 mmol) 4·[(1Ε)-3-酮基_3-({2,2,2-三 氣-l-[3-(二氟曱基)苯基]乙基胺基)丙稀_i_基]_2_(三戴 曱基)苯甲酸(來自實例2,步驟2)溶於1如二氣曱烧。然後 添加17 mg (1.0 eq,0.10 mmol) 6-氯經基笨并三唑、23 mg (1·2 eq,0.12 mmol) N-(3-二曱基胺基丙基)_^,_乙基碳化二 亞胺鹽酸鹽及26 mg (2 eq,0.20 mmol) N-乙基二異丙基胺, 於室溫下攪拌混合物20分鐘,隨後’添加U mg (丨〇 eq,〇 jo mmol) 1-氟丙烷-2-胺鹽酸鹽,於室溫下攪拌反應混合物12 h。之後,反應混合物濃縮及所得粗產物經製備性hplc純 化(phenomenex Gemini C18 5μιη; 110A; AXIA 50x21.2mm; 梯度:0-2分鐘70%水、30% MeOH,2.5-6.0分鐘線性梯度至 5%水、95%1^011,6.0-20.00分鐘5%水、95%1^011;依2 ml/min 添加改質劑:20% HCOOH)。產生27 mg (37%) N-(l- 氟丙烧-2-基)·4-[(1Ε)-3-酮基-3_({2,2,2-三氟小[3_(三氟曱基) 本基]乙基}胺基)-丙_1_烯-1-基]-2-(三氟甲基)苯曱醯胺之固 體。 HPLC-MS : logP = 3.37,質量(m/z) : 544.96 (M+H)+。 ]H NMR (400 MHz, d6-DMSO) : δ = 9.51 (d, 1Η), 8.60 (d, 1H), 8.05 (s, 1H), 8.00 (s, 1H), 7.95 (m, 2H), 7.80 (d, 1H), 7.72 (t, 1H), 7.66 (d, 1H, J=16Hz), 7.55 (d, 1H), 6.96 (d, 1H, 129 201136518 J—16 Hz),6.17 (m,1H),4.38 (dd,2H,1J(H,F)= 47Hz 及 J(H,H)=5Hz),4.20 (m,1H),1.15 (d,3H) 合成實例3 (通式及1-12化合物依據化學式反應流程6之 製法) 步驟1 (2E)-3-(3-硝基苯基)-N_{2,2,2-三氟-1-【3-(三氟甲基)苯基]乙 基}丙稀酿胺
先添加3〇〇 mg (1.23 mmol) 2,2_三氟·(三氟曱基)苯 基]乙胺(參考文獻DE 2723464)及137 mg (1.35 mmol)三 乙基胺至2 ml二氯曱烧中,添加261 mg (1.23 mmol) (2Ε)·3_(3·硝基苯基)丙烯醯氯之溶液(由(2E)-3-(3-硝基苯基) 丙稀酸與草醯氯反應合成)。於室溫下攪拌反應溶液18小時 後’以二氣曱烷稀釋,以水洗滌3次,及經硫酸鈉脫水。減 壓蒸餾排除溶劑,殘質與二異丙基醚攪拌。 產量:417 mg (理論值之69.5%)。 !H NMR (400MHz, d6-DMSO)5= 6.10 (m, 1H), 7.00 (d, 1H), 7.6 (d, 1H), 7.75 (m, 1H), 7.8 (m, 3H), 7.85 (m, 2H), 7.89 (m, 1H),7.99 (m,1H),9.43 (d,1H)。 HPLC-MS : logP = 3.81;質量(m/z) : 419.1 (M+H)+. 130 201136518 步驟2 (2E)_3-(3-胺基苯基)-N-{2,2,2-三氟小[3-(三氟甲基)苯基】乙 基}丙烯醯胺
先添加626 mg (3.30 mmol) Sn(II)Cl2 至5 ml 乙醇中,及 添加350 mg (〇.83mmol) (2E)-3-(3-硝基苯基)-N-{2,2,2-三 氟-l-[3-(三氟曱基)苯基]乙基卜丙烯醯胺(來自實例3,步驟 1 )。於回流溫度下攪拌反應溶液1小時,冷卻及與50 ml水 混合。使用冰冷卻期間,以濃氫氧化鈉溶液調整pH至9,再 以二氣曱烷萃取混合物。有機相經硫酸鈉脫水,減壓蒸餾 排除溶劑,殘質與二異丙基醚攪拌。 產量:279 mg (理論值之74.6%)。 !H NMR (400MHz, d6-DMSO) δ= 6.08 (m, 1Η), 6.65 (m, 1H), 7.6 (d, 1H), 7.75 (m, 1H), 7.04 (m, 1H), 7.38 (m, 1H), 7.68 (m, 1H),7.75 (m,1H),7.90 (m, 1H),7.99 (m,1H),9.25 (m,1H)。 HPLC-MS : logP = 2.88;質量(m/z) : 389.1 (M+H)+. 步驟3 2-氯-Ν-{3·[(1Ε)-3·酮基-3-({2,2,2-三氟-l-[3-(三氟甲基)苯 基】乙基}胺基)丙小烯-1-基]苯基}菸醯胺(表1化合物la-5) 131 201136518
先添加 100 mg (0.25 mmol) (2Ε)-3-(3·胺基笨 基):Ν·{2,2’2-三氣小[3_(三氟甲基)苯基]_乙基}丙婦“ 自貫例3,步驟2)及33.8 mg (0.33 mmol)三乙基胺至丄二 氯曱烧中,添加含49.8 mg (0.33 mmol) 2-氯柊醯氣之J 三氣曱烷溶液。於室溫下攪拌反應溶液18小時後,以二氣 曱烷洗滌,以水洗滌3次,及經硫酸鈉脫水。減壓蒸餾排除 溶劑,殘質經製備性HPLC純化(溶劑=水(A) +乙猜 (B),梯度=40分鐘,自 1〇%Β 至 100%B,流速=18ml/min)。 產量:80.0 mg (理論值之58.9%)。 ]H NMR (400MHz, d6-DMSO)5= 6.08 (m, 1H), 6.83 (d, 1H), 7.36 (m, 1H), 7.40 (m, 1H), 7.52 (m, 2H), 7.72 (m, 1H), 7.75 (m, 1H), 7.89 (m, 1H), 7.99 (m, 1H), 8.05 (m, 1H), 8.12 (m, 1H),8.52 (m,1H),9.38 (m,1H)。 HPLC-MS : logP = 3.39;質量(m/z) : 528.1 (M+H)+. 合成實例4 (通式1-1及II-l化合物依據化學式反應流程1及7 之製法) 步驟1 1-[3-氯-5-(三氟甲基)苯基1-2,2,2-三氟乙胺 132 201136518
在附加低溫溫度計、滴加漏斗及氬氣球之500 mi多爱貝 燒瓶中,以120ml乙醚保護5.5 g (0.228 mol,1.3 eq)鎮旋屑 (經二溴乙烷活化,及以乙醚洗滌)。於0〇C下,慢慢添加 含 45.5 g 3·溴-5-氯三氟甲苯(0.175 mol, 1 eq)之 120 ml 乙 峻。幾分鐘後,自發性開始反應,並出現顏色變化(紅褐色) 及升温;添加期間之溫度保持在約0。〇 —旦溴化物添加完 畢時,即進一步攪拌混合物30分鐘。 在另一個附加低溫溫度計、滴加漏斗及氬氣球之2升 二頸燒瓶中先添加含32.4 g三氟乙酸乙酯(0.228 mol,1.3 eq) 之250 ml乙醚,及冷卻至_8〇〇c。於此溫度下,慢慢滴加 格林納試劑(冷卻至 — iOcC)。添加完畢時,反應混合物於 -80°C下再擾拌30分鐘。然後使反應混合物回升至_1〇〇c, 以10/。鹽I酸化。所得混合物與飽和Naci溶液混合’分 相,水相經200-300 ml乙醚洗滌。合併之醚相經硫酸鎂脫 水,隨後於旋轉蒸發器上排除溶劑。 所得粗產物經真空蒸餾純化(71〇c,18 mbar)。得到37.7 g (理論值之78%) 1-[3-氣_5_(三Λ曱基)苯基]_2,2,2·三敗乙 酮之無色油狀物。此產物未再純化即進一步轉化。 在含24.5 g 1·[3-氣-5-(三氟曱基)苯基]_2,2,2_三氟乙酮 (88mmol,1 eq)之2〇〇瓜丨曱苯溶液中添加13 6 g間胺基曱 133 201136518 基)苯曱基胺(100 mmol,1.13eq)。添加觸媒量之p-Ts0H.H20 (〜lOOmg)後’混合物於水分離器上回流12 h (排出約5 ml 水)。然後再添加5.5 g間-(胺基曱基)苯曱基胺(40 mmol), 混合物進一步煮沸11小時。隨後,蒸餾排除曱苯(760托)。 所得粗產物於高度真空(3〇-1〇5。(:,0.5托)下蒸餾。進一步 利用維格羅(Vigreux)管柱(25托下之b.p. 105-108°C)蒸餾, 產生16.0 g l-[3-氣-5-(三氟曱基)苯基]-2,2,2-三氟乙胺(58 mmol, 65%)之透明液體。 HPLC-MS : logP = 2.94,質量(m/z) : 277.93 (M+H) !H NMR (400 MHz, d3-CD3CN) : δ = 7.75 (m, 3Η), 4.60 (m, 1H), 2.10 (s, 2H,br)。 類似步驟1所說明l-[3-氯-5-(三氟曱基)苯基]-2,2,2-三 氟乙胺之製法,亦得到下列化合物: 2,2,2-三氟-1-(3,4,5-三氣苯基)乙胺 HPLC-MS : logP = 3.17;質量(m/z) : 277.9 ; 279.9 (M+H)+. 'Η NMR (400MHz, d6-DMSO) δ = 7.84 (s, 2H), 4.63 (m, 1H), 2.72 ppm (br. s, 2H)。 步驟2 4-溴-N-環丙基-2-(三氟曱基)苯甲醯胺
取1.50 g (1 eq,5.57 mmol) 4-溴-2-(三氟甲基)苯曱酸 (類似 EP1445253 Yamanouchi Pharmaceutical Co·之說明, 134 201136518 由苯曱酸進行溴化反應後合成)溶於5 ml二氣曱烷。然後添 加954 mg (1.〇 eq,5.57 mmol) 6-氣羥基苯并三唑、1.28 g (1.2 eq,6.69 mm〇l) Ν·(3_二曱基胺基丙基)N,乙基碳化二亞胺 鹽酸鹽及1.45 ml (1.5 eq,8.63 mmol) N-乙基二異丙基胺,於 室溫下攪拌混合物2〇分鐘,隨後,添加477 mg (1.5 eq,8.36 mmol)環丙基胺,及於室溫下攪拌反應混合物12h。然後混 合物減壓濃縮,粗產物溶於乙酸乙酯(EA)。溶液經2χ緩衝 液(0.5 Μ磷酸鹽緩衝液ρΗ=7)洗滌後,經MgS04脫水。使用 溶離劑環己烷/乙酸乙酯(EA)(〇% EA至100% EA)進行矽膠 層析法純化。產生831 mg (48%) 4-溴-N-環丙基-2-(三氟曱 基)苯甲醯胺之白色固體。 HPLC-MS : logP = 2.13;質量(m/z) : 309.91 (M+H)+. ]H NMR (400 MHz, d3-CD3CN) : δ = 8.26 (s, 1H, br), 7.90 (s, 1H), 7.88 (d, 1H), 7.43 (d, 1H), 2.80 (m, 1H), 0.70 (m, 2H), 0.50 (m,2H). 類似合成實例4,步驟1說明之方法,得到下列化合 物: 4-溴-N-(吡啶-2-基)-2-(三氟甲基)苯甲醯胺 由4-溴-2-(三氟曱基)苯曱酸製備。 HPLC-MS : logP = 2.57;質量(m/z) : 344.92 (M+H)+. JH NMR (400 MHz, d3-CD3CN) : δ = 8.90 (s, 1H, br), 8.30 (d, 1H), 8.15 (d, 1H), 7.95 (s, 1H), 7.85 (d, 1H), 7.80 (dd, 1H), 7.60 (d, 1H)? 7.13 (m, 1H). N-苯甲基-4-溴-2-(三氟甲基)苯曱醯胺 135 201136518 由4-溴-2-(三氟曱基)苯曱酸製備。 HPLC-MS : logP = 2.89;質量(m/z) : 359.85 (M+H)+. *H NMR (400 MHz, d3-CD3CN) : δ = 7.90 (s, 1H), 7.80 (dd, 1H), 7.45 (d, 1H), 7.35 (m, 5H), 7.30 (m, 1H), 4.50 (d, 2H). 4-溴-N-(”比啶-2-基甲基)-2-(三氟甲基)苯甲醯胺 由4-溴-2-(三氟曱基)苯曱酸製備。 HPLC-MS : logP= 1.56;質量(m/z) : 360.91 (M+H)+. ]H NMR (400 MHz, d3-CD3CN) : δ = 8.50 (d, 1H), 7.90 (s, 1H), 7.85 (d, 1H), 7.73 (dd, 1H), 7.50 (d, 1H), 7.35 (d, 1H), 7.30 (s, 1H, br), 7.23 (m, 1H), 4.60 (d, 2H). 4-漠-2 -甲基-N-(0比咬-2-基甲基)苯甲酿胺 由4-溴-2-曱基苯曱酸製備。 HPLC-MS : logP= 1.40;質量(m/z) : 306.95 (M+H)+. ]H NMR (400 MHz, d3-CD3CN) : δ = 8.50 (t, 1H), 7.73 (t, 1H), 7.45 (s, 1H), 7.40 (d, 1H), 7.35 (m, 3H), 7.20 (dd, 1H), 4.60 (d, 2H),2.40 (s,3H)。 4-溴-N-環丙基-2-甲基苯甲醯胺 由4-溴_2-曱基苯甲酸製備。 ]H NMR (400 MHz, d3-CD3CN) : δ = 7.45 (s, 1H), 7.35 (d, 1H), 7.20 (d, 1H), 6.80 (s, 1H, br), 2.80 (m, 1H), 2.40 (s, 3H), 0.70 (m, 2H), 0.55 (m, 2H). 步驟3 (2E)-3-[4-(環丙基胺曱醯基)-3-三氟曱基苯基]丙烯酸 136 201136518
在30 ml微波反應管中,取1.18 g (1 eq,3.84 mmol) 4-溴-N-環丙基-2-(三氟曱基)笨曱醯胺及868 mg (1 eq,3.84 mmol)(2E)_3-(4,4,5,5-四甲基-1,3,2-二氧硼雜環戊-2-基)丙 烯酸乙酯溶於8 ml 1,4-二氧雜環己烷。在其中添加9 ml Na2C03 (2M7jc溶液)及283 mg (0.1 eq, 0.38 mmol)雙(三環 己基膦)-鈀(II)二氣化物,以氬氣飽和反應混合物5分鐘。然 後使反應混合物於微波爐(CEM Discover)中,在150°C (80 瓦)下加熱10分鐘,隨後,傾析排除二氧雜環己烷溶液,殘 質經1,4-二氧雜環己烷洗滌,合併之有機相減壓濃縮。殘質 溶於水中,以少量乙醚洗滌。隨後,混合物經1 M HC1酸化 至ρΗ=3,水溶液經乙酸乙酯(ΕΑ)萃取。有機相脫水後,濃 縮,得到412mg(35%)(2E,Z)-3-[4-(環丙基胺曱醯基)-3-(三 氟曱基)苯基]丙烯酸之白色固體。 HPLC-MS : logP = 1.34,質量(111/2):300.03 (]^+11)+· *H NMR (400 MHz, d3-CD3CN) : δ = 7.90 (s, 1H), 7.80 (d, 1H), 7.70 (d, 1H, J= 16Hz), 7.50 (d, 1H), 6.60 (s, 1H, br), 6.55 (d, 1H, J- 16Hz), 2.80 (m, 1H), 0.75 (m, 2H), 0.55 (m, 2H). 類似合成實例4,步驟2說明之方法’亦製得下列通 式II-1化合物: 137 201136518 (2Ε)-3-[4-(»比啶-2-基)胺甲醯基)-3-三氟甲基苯基】丙烯酸 由4-漠基)-2-(二氟1曱基)苯曱酿胺製備。 HPLC-MS : logP = 1.69;質量(m/z) : 337.04 (M+H)+. ]H NMR (400 MHz, d3-CD3CN) : δ = 8.30 (d, 1H, br), 8.15 (m, 2H), 8.00 (s, 1H), 7.90 (d, 1H), 7.80 (m, 1H), 7.60 (m, 2H), 7.10 (m, 1H), 6.60 (d, 1H, J= 16Hz). (2E)-3-[4-(苯基曱基)胺甲醯基)-3-三氟甲基苯基】丙烯酸 由N-苯曱基-4-溴-2-(三氟曱基)苯曱醯胺製備。 HPLC-MS : logP = 2.12,質量(m/z) : 350.1 (Μ+Η)+· !H NMR (400 MHz, d3-CD3CN) : δ = 7.98 (s, 1H), 7.88 (d, 1H), 7.70 (d, 1H, J= 16Hz), 7.55 (d, 1H), 7.35 (m, 5H), 7.29 (m, 1H, br), 6.60 (d, 1H, J= 16Hz),4.51 (d,2H)。 (2E)-3-[4-("比啶-2-基甲基)胺甲醯基)-3-三氟甲基苯基】丙烯 酸 由4-溴-N-(吼啶-2-基曱基)-2-(三氟曱基)苯曱醯胺製 備。 HPLC-MS : logP = 0.91;質量(m/z) : 350.9 (M+H)+. (2E)-3-[4-(環丙基胺甲醯基)-3-曱基苯基】丙烯酸 由4-溴-N-環丙基-2-(曱基)苯曱醯胺製備。 HPLC-MS : logP= 1.14;質量(m/z) : 246.09 (M+H)+. *H NMR (400 MHz, d3-CD3CN) : δ = 7.60 (d, 1H, J= 16Hz), 7.45 (m, 2H), 7.30 (d, 1H), 7.20 (d, 1H), 6.45 (d, 1H, J= 16Hz), 2.90 (m, 1H), 2.35 (s, 3H), 0.75 (m, 2H), 0.55 (m, 2H). 138 201136518 步驟4 4·[(1Ε,Ζ)-3-({1-[3-氯-5-(三氟甲基)苯基】-2,2,2-三氟乙基} 胺基)-3-嗣基丙-1-稀-1-基】-N-環丙基-2-(三氣甲基)苯曱酿 胺(表1之化合物編號la-40)
取 100 mg (1 eq,0.29 mmol) (2E,Z)-3-[4-(環丙基胺曱醯 基)-3-(三氟曱基)苯基]-丙烯酸溶於1 ml二氣甲烧。然後添加 50 mg (1.0 eq, 0.29 mmol) 6-氯經基苯并三《坐、73 mg (1.3 eq, 0.38 mmol) #-(3-二甲基胺基丙基)-Ν’-乙基-碳化二亞胺鹽 酸鹽及102 μΐ (2 eq,0.58 mmol) Ν-乙基二異丙基胺,於室溫 下攪拌混合物20分鐘,隨後,添加98 mg (1.3 eq,0.35 mmol) l-[3-氣-5-(三氟曱基)苯基]-2,2,2-三氟乙胺,及於室溫下攪 拌反應混合物12 h。然後混合物減壓濃縮,粗產物溶於乙酸 乙酯(EA)。溶液經缓衝液(0.5M磷酸鹽緩衝液,PH=7)洗滌 2次,經MgS04脫水。使用溶離劑環己烷/乙酸乙酯(ΕΑ)(0〇/〇 EA至100% EA)進行矽膠層析法純化。產生61 mg (37%) 4-[(1Ε,Ζ)-3-({1-[3-氯-5-(三氟曱基)苯基]-2,2,2-三氟乙基} 胺基)-3-酮基丙-1-烯-1-基]_N-環丙基-2-(三氟曱基)苯曱醯 胺之固體。 HPLC-MS : logP = 3.68,質量(m/z) : 558.97 (M+H)+. ι¥ί NMR (400 MHz, d6-DMSO) : δ = 9.51 (d, 1H), 8.55 (d, 1H), 139 201136518 8-12 (s, 1Η), 8.08 (s, 1H), 8.03-7.95 (m, 2H), 7.93 (d, 1H), 7-66 (d, 1H, J=l6Hz), 7.54 (d, 1H), 6.93 (d, 1H, J=16 Hz), 6-26 (m, 1H), 2.79 (m, 1H), 0.70 (m, 2H), 0.50 (m, 2H) 合成實例5 (通式1-1及II-2化合物依據化學式反應流程1及8 之製法) 步驟1 (2E)-3_[3-氦基-4-(m-l,2,4-三唑-1-基)苯基】丙烯酸
取2.05 g (10.3 mmol) 5-曱醯基-2-(1Η-1,2,4-三唑-1-基) 苯基氰(參考文獻:WO-A-2008/019760)、1.60 g (16.6 mmol) 丙二酸及176 mg (2.07 mmol)哌啶於20 m卜比啶中,在80oC 下授拌48小時。減壓蒸餾排除吡咬。添加殘質至冰水中, 以濃鹽酸調整至pH 1。水相經乙酸乙酯重覆萃取,及經硫 酸鈉脫水,及減壓蒸餾排除溶劑。 產量:2.00 g (理論值之77°/〇)。 HPLC-MS : logP = 0.97;質量(m/z) : 241.1 (M+H)+. 步驟2 (2E)-3-[3_氰基-4_(1Η-1,2,4-三唑-1-基)苯基]丙烯酸(表1之 140 201136518 化合物編號Ia-17)
先添加 100 mg (0.41 mmol) 2(2E)-3-[3-氣義 -4-(111-1,2,4-三唑-1-基)苯基]丙烯酸(來自實例5,步驟7) 及 96.0 mg (〇·5〇 mmol) EDC 至 2 ml 二氧雜環己烷中,0 拌30分鐘。然後添加101 mg (0.41 mmol) 2,2,2-三氟七[3 4 二氯苯基]乙胺(CAS註冊編號:886369-74-0),於室斤下 再攪拌混合物18小時。於旋轉蒸發器蒸餾排除二氧雜環已 烷,殘質溶於水中’以乙酸乙酯重覆萃取。有機相經^酸 鈉脫水,於旋轉蒸發器上蒸餾排除溶劑。殘質經石夕膠使用 環己烧/乙酸乙酯作為溶離劑進行層析法(梯度=2小時 自0%乙酸乙酯至100%乙酸乙酯)。 產量:69.0 mg (理論值之62%)。 ]H NMR (d6-DMSO) δ = 6.05 (m, 1H), 6.95 (d, 1H), 7.62 (m 2H),7.71 (m,1H),7.94 (m,1H),8.08 (m,1H),8.29 (m,1H)’ 8.35 (m,1H),9.18 (s,1H),9.35 (d,1H)。 ’ HPLC-MS : logP = 3.22;質量(m/z) : 466.0 (M+H)+ 合成實例6(通式1-1及1-9化合物依據化學式反應流程丨及5之 製法) 步驟1 141 201136518 5-氰基-N_{2,2,2_三氟小[3-(三氟甲基)苯基】乙基}小苯并呋 喃-2-羧醢胺衍生物(表3之化合物編號Ic l)
取含2,2,2-三氟小[3-三氣曱基笨基]乙胺(4〇〇邮,164 mmol)之N,N-二曱基曱醯胺(5 ml)溶液與5_氰基苯并呋喃_2_
水,過濾及減壓濃縮。殘質經矽膠使用環己烷/乙酸乙s旨作 為溶離劑進行層析法(梯度=2小時,自0%乙酸乙g旨至2〇% 乙酸乙酯)。 產量:467.6 mg (理論值之68%)。
HPLC-MS : logP = 3.63;質量(m/z): 413.0 (M+H)+; ]H NMR (CD3CN) 6.06 - 6.12 (m,1H),7.60 (s,1H),7.64 - 7.68 (m, 1H), 7.73 - 7.80 (m, 4H), 7.85 - 7.87 (m, 1H), 7.95 (m, 1H), 8.16 (m,1H)。 步驟2 142 201136518 5-(胺基曱基)-N-{2,2,2-三氟-l-[3-(三氟曱基)苯基】乙基}-l-苯并呋喃-2-羧醯胺衍生物
取含5-氰基-N-{2,2,2-三氟-1-[3-(三氟曱基)苯基]乙 基}-1-苯并咬喃-2-魏蕴胺衍生物(273 mg, 0.66 mmol)之曱 醇(10 ml)溶液與濃鹽酸(0.42 ml)及鈀/碳(10%; 50 mg)混 合,及於氫氣壓下攪拌2 h。反應混合物經Celite®及矽膠填 料過濾、。 產量:297.4 mg (理論值之107%)。
HPLC-MS : logP = 2.02;質量(m/z) : 415.1 NMR (CD3CN) 3.90 (s,1H),6·09 (m,1H),7.42 - 7.68 (m,6H), 7.74 - 8.07 (m,5H)。 步驟3 5-(乙醯胺基曱基)-N-{2,2,2-三氟-l-[3-(三氟曱基)苯基】乙 基}-1-苯并呋喃-2-羧醯胺衍生物(表3之化合物Ic-10) 143 201136518
INI
〇K 取含5-(胺基曱基)-N-{2,2,2-三氟-l-[3-(三氟甲基)苯基] 乙基}-1-苯并α夫喃-2-叛醯胺衍生物(50 mg, 0.12 mmol)之 二氯曱烷(1 ml)溶液與吡啶(0.01 ml)混合,及冷卻至0°C。 然後滴加乙酷氯(9 μΐ, 0.12 mmol),使混合物回升至室溫一 夜。以乙酸乙酯稀釋混合物,以鹽酸(1 M)洗滌。有機相經 硫酸鈉脫水,過濾及減壓濃縮。殘質使用水/乙腈作為溶離 劑進行製備性HPLC層析法(梯度=43分鐘,自10%乙腈之 水溶液至100%乙腈)。 產量:10.8 mg (理論值之19%)。 HPLC-MS : logP = 2.80;質量(m/z) : 459.1 (M+H)+; W NMR (CD3CN) 2.15 (s, 3H), 4.41 (d, 2H), 6.13 (quint, 1H), 6.88 (br. s, 1H), 7.40 - 7.42 (m, 1H), 7.51 - 7.56 (m, 2H), 7.62 - 7.69 (m, 2H), 7.76 - 7.78 (m, 1H), 7.88 - 7.90 (m,1H),7.97 - 7.99 (m,1H),8.21 - 8.23 (m,1H)。 合成實例7 (通式1-6及II-3化合物依據化學式反應流程1、4 及9之製法) 步驟1 4-曱醯基-3-羥基苯甲酸第三丁酯 144 201136518
取4-甲醯基-3-羥基苯甲酸(1 g,6 〇爪们 喃(10 ml),並回流加熱。然後滴加N,N_二甲 三丁基縮酿(5.77 1111,24.0111111〇1),於該溫^ 1.5 h。冷卻之溶液減壓濃縮,殘質經石夕膠偵 乙酯作為溶離劑進行層析法(梯度=1小時, 至5%乙酸乙酯)。 g,6·0 mm〇i)溶於四氫咬 7N,N-一甲基甲隨胺二_第 ’於該溫度下攪拌混合 ----什、/¾合物殘質經矽膠使用環己烷/乙酸 ^度=1小時,自〇%乙酸乙gt 產量:1.13 g (理論值之84%)。 HPLC-MS : logP = 3.11;質量(m/z) : 223.1 (M+H)+; Ανμ (CD3CN) 1.58 (s,9Η),7.48 (s,1Η),7.57 (d,1Η),7.76 / 1H)。 ,’(d, 步驟2 1-苯并吱嗔-2,6-二叛酸2-乙醋6-第三丁酉旨
取含4-甲醯基-3-羥基苯甲酸第三丁酯(1.2 g,5>4q mmol)及碳酸鉀(1726 mg, 12.4 mmol)之 DMF (17 ml)溶液, 滴加〉臭乙酸乙酯(0.56 ml,5.0 mmol)混合,於80〇C下授掉6 h。然後再度添加溴乙酸乙酯(0.28 ml,2.5 mmol),於8〇〇c 下擾拌混合物一夜。冷卻至室溫後,添加反應混合物至冰 水中’以乙酸乙酯萃取。有機相經硫酸鈉脫水,過遽及 壓濃縮至乾。 ~ ' 145 201136518 產量497.3 mg (理論值之32%)。 HPLC-MS : logP = 4.32;質量(m/z) : 235.1 (M-C4H9+2H)+; *H NMR (CD3CN) 1.38 (t, 3H), 1.60 (s, 9H), 4.40 (q, 2H), 7.59 (s, 1H), 7.79 (d, 1H),7.93 (d,1H),8.19 (s,1H)。 步驟3 6-(第三丁氧基羰基)-1-苯并呋喃-2-羧酸
I
取含1-苯并呋喃-2,6-二羧酸2-乙酯6-第三丁酯(490 mg, 1.68 mmol)之乙醇(15 ml)溶液與氫氧化納溶液(3.36 ml, 1 Μ)混合,及回流加熱2 h。添加冷卻之溶液至冰冷之鹽酸 (1 M)中,抽吸濾出沉澱物,以少量水洗滌及減壓乾燥。 產量:353 mg (理論值之80%)。 HPLC-MS: logP = 2.58;質量(m/z): 261.1 (M+H)+; 4 NMR (CD3CN) 1.60 (s, 9H), 7.60 (s, 1H), 7.79 (d, 1H), 7.92 - 7.94 (m,1H),8.19 (s,1H)。 步驟4 2-«2,2,2-三氟-l-[3-(三氟曱基)苯基]乙基}胺曱醯基)-1-苯 并呋喃-6-羧酸第三丁酯
取含6-(第三丁氧基羰基)-1-苯并呋喃-2-羧酸(350 mg, 146 201136518 1.33 mmol)及2,2,2-二乱-l-[3-二氟甲基笨基]乙胺(357 mg, 1.46 mmol)之N,N-二曱基曱醯胺(5 ml)溶液與4·(46_二甲氧 基[1.3.5]二11井-2-基)-4-甲基嗎嚇錄氯化物水合物(go* mg, 1.46 mmol)混合’於密閉容器中及5〇。〇下攪拌一夜。冷卻之 反應溶液與鹽酸(1 M)混合’以乙酸乙酯萃取。有機相經飽 和碳酸氫納溶液及飽和氣化納溶液洗務,經硫酸納脫水, 過濾及減壓濃縮至乾。留下453 mg之第三丁醋與游離酸之 混合物,其未再進一步純化即用於下一個步驟。 步驟5 2·({2,2,2·三氟-1-[3-(三氟曱基)苯基】乙基)胺甲醯基)小苯 并呋喃-6-羧酸
取含2-({2,2,2-三氟-1-[3-(三氟曱基)苯基]乙基}胺曱醯 基)_1_苯并呋喃-6-羧酸第三丁基酯(450 mg,1.04 mmol)之二 氣甲烷(4.5 ml)溶液,於〇°C下與三氟乙酸(0.46 ml,6.0 mmol)混合,及於室溫下攪拌一夜。隨後,以水洗滌反應混 合物,有機相經硫酸鎂脫水’過濾及減壓濃縮。殘質經矽 膠過濾’濾餅經乙酸乙酯及曱醇洗滌,取濾液濃縮。 產量:266 mg (理論值之59%)。 HPLC-MS : logP = 3.10;質量(m/z) : 430.1 (M-H)_; 4 NMR (CD3CN) 6.05 - 6.10 (m,1H),7.52 - 8.19 (m,9H)。 步驟6 147 201136518 N6-環丙基-N2-{2,2,2A氟_1_[3-(三氟甲基)苯基]乙基卜:奸 并吱喃-2,6-二羧醯胺衍生物(表3之化合物1(>19) 本
A) 1取二氟-1-[3 (三氟曱基)苯基]乙基}胺甲酿 巷)1本并0夫喃-6-羰酸(1〇〇 mg, 0.21 mmol)之Ν,Ν-二甲其 醯胺(1 ml)溶液與4-(4,6-二曱氧基[1.3.5]三畊-2-基土甲 嗎琳鏽氣化物水合物(100 mg, 0.46 mmol)及環汚基胺甲基 mg,0.63 mmol)混合,於密閉容器中及50〇c下攪拌—=。(36 卻之反應溶液與鹽酸(1 M)混合,以乙酸乙酯萃取。有機= 經飽和碳酸氫鈉溶液及飽和氯化鈉溶液洗滌,經硫酸鈉= 水,過濾及減壓濃縮至乾。殘質使用水/乙腈作為溶離劑進 行製備性HPLC層析法(梯度=43分鐘,自10%乙腈之水溶 液至100%乙腈)。 ^ 產量:18.2 11^(理論值之18〇/0)。
HPLC-MS : logP = 3.25;質量(m/z) : 471.1 (M+H)+; 4 NMR (CD3CN) 0.61 - 0.65 (m, 2H), 0.75 - 0.79 (m, 2H), 2.85 -2.91 (m, 1H), 6.14 (quint, 1H), 7.18 (br. s, 1H), 7.58 (s, 1H), 7.69 - 7.79 (m, 4H), 7.89 - 7.91 (m, 1H), 7.97 - 7.99 (m, 2H), 8.28 (d,1H)。 合成實例8 (通式及II-4化合物依據化學式反應流程1、4 148 201136518 及10之製法) 步驟1 4-胺基-2-氣-5-埃苯甲酸乙醋 0 产(/γγ| c丨人乂 νη2 取碘之乙醇溶液與硫酸銀(I)及4-胺基-2-氣苯曱酸乙酯 混合’於室溫下攪拌45分鐘。反應混合物經玻璃濾片過濾, 濾液減壓濃縮。殘質於EtOAc中形成漿物,與稀釋之碳酸氫 鈉溶液混合。一旦完全形成溶液時,及排出水相,使硫代 硫酸鈉在其中溶解。再以水相洗滌有機相,以乙酸乙酯萃 取水相。合併之有機相經硫酸鈉脫水,過濾及減壓濃縮。 管柱經矽膠使用環己烷/乙酸乙酯作為溶離劑進行層析法純 化(自10%乙酸乙酯至33%乙酸乙酯之梯度)。 產量:1.85 g (理論值之74%)。
HPLC-MS : logP = 2.95;質量(m/z) : 326.0 (M+H)VH NMR (CD3CN) 1.32 (t, 3H), 4.27 (q, 2H), 5.01 (br. s, 2H), 6.80 (s, 1H),8.16 (s,1H)。 步驟2 6-氯-5-(乙氧基幾_基)-1 H_〇弓丨蜂-2-缓酸 Ο
於氬氣壓下,取含4-胺基-2-氣-5-碘苯曱酸乙酯(1.82 g, 149 201136518 5.59 _!)之N,N_二甲基甲醯胺(18如)溶液與丙酮酸(ι 27 mi,18.2mm〇1)M,4-重氮雙環[2.2.2]辛妓合,抽真空及 充入氬氣。使氬氣通過溶液5分鐘後,添加乙酸轉)(68哪 0.30 _。1),加熱混合物錢代2小時。冷卻之溶液經 Cdite過遽,渡餅經乙酸乙醋(議吨洗;條。遽液(懸浮液) 經鹽酸(2 M; 2 x、25 ml)及水(2 X 25 ml)洗條,經硫酸納脫水 及過濾、。滤液減壓濃縮至乾,產生紅褐色固體(i 93 g,約 51%產物)’其未再進一步純化即用於下—個步驟。 步驟3 6-氣-2-({2,2,2-三敦-H3-(三氟甲基)苯基】乙基}胺甲醯 基)-1Η-β弓丨哚-5-羧酸乙酯
取含粗產物6-氣-5-(乙氧基羰基羧酸(1 9 g) 及2,2,2-三氟-ΐ-[3·三氟曱基苯基]乙胺〇 12 g,4 6〇麵叫 之>^-二曱基曱醯胺(15 1111)溶液與4-(4,6-二甲氧基[1.3.5] 三4-2-基)-4-曱基嗎啉鑌氯化物水合物(953 mg,4 6〇 mm〇1) 混合’於室溫下攪拌4天。反應溶液與鹽酸(丨μ)混合,以乙 酸乙酯萃取。有機相經飽和碳酸氫鈉溶液及飽和氯化鈉溶 液洗滌。經硫酸鈉脫水,過濾及減壓濃縮至乾。使用環己 烷/乙酸乙酯作為溶離劑進行矽膠管柱層析法(自1〇%乙酸 乙酯至25%乙酸乙酯之梯度)。 150 201136518 產量:603 mg (2個步驟為理論值之26%)。 HPLC-MS: logP = 4.12;質量(m/z): 493.1 (M+H)+; WNMR (CD3CN) 1.38 (t, 3H), 4.35 (q, 2H), 6.16 (quint, 1H), 7.36 (s, 1H), 7.58 (s, 1H), 7.65 - 7.69 (m, 1H), 7.76 - 7.79 (m, 1H), 7.87 - 7.89 (m, 1H), 7.98 (s, 1H), 8.07 - 8.09 (m, 1H), 8.25 (s, 1H), 10.22 (s, 1H)。 步驟4 6-氣_N5-環丙基-N2-{2,2,2-三氟-l-[3-(三氟曱基)苯基]乙 基}-1仏吲哚-2,5-二羧醯胺衍生物(表3之化合物Ic-24)
取含6-氯-2-({2,2,2-三氟-l-[3-(三氟曱基)苯基]乙基} 胺曱醯基)-111_°引〇朵-5-叛酸乙酉旨(590 mg,1.18 mmol)之曱醇 (8 ml)溶液與氫氧化鈉溶液(1 M,4.2 ml)混合,於回流下攪 拌一夜。添加冷卻之溶液至冰冷鹽酸(1 M)中,抽吸濾出沉 殿,以少量水洗滌及減壓乾燥。殘留之固體(366 mg)未再進 一步純化即用於下一個步驟。 取一部份所得產物(121 mg)溶於N,N-二曱基曱醯胺 (1.5 ml) ’ 與環丙基胺(12 mg, 0.20 mmol)、HBTU (99 mg, 0.26 mmol)及N-曱基嗎啉(67 mg,0.6ό mmol)混合,於室溫 下稅拌一仪。隨後,反應混合物減|濃縮,溶於乙酸乙酯, 依序以碳酸氫鈉溶液(10%)及飽和氣化鈉溶液洗滌。有機相 151 201136518 經硫酸鈉脫水,過濾及減壓濃縮。殘質使用水/乙腈作為溶 離劑進行製備性HPLC層析法(梯度=43分鐘,自10%乙腈之 水溶液至100%乙腈)。 產量:6.4 mg (理論值之3%)。 HPLC-MS : l0gp = 3.08;質量(m/z): 5〇4 j (M+H)+; iH NMR (CD3CN) 0.56 - 0.60 (m,2H),〇.74 - 0.78 (m,2H),2.83-2.87 (m,1H),6.14 (quint, 1H),6.86 (s, 1H),7.29 (s,1H), 7.52(s,lH),7.64 - 7.68 (m,lH),7.76 - 7.77 (m,2H),7.88-7.90 (m,1H),7.97 (s,1H),8.08 - 8.01 (m,1H),10.19 (s, 1H)。 合成實例9(通式1-14化合物依據化學式反應流程6a及19 之製法) 步驟1 (2Ε)-3-[4-(Ν·-經基曱脒基)_3_(三氟曱基)苯基]_N_{2,2,2三 氟-1_[3-(三氣曱基)苯基】乙基}丙烯醯胺
先添加實例 la-46 之 1.17 g (2.51 mmol) (2E)-3-[4-氰基 冬(三氟曱基)苯基]-Ν-{2,2,2-三敗小[3-(三氟曱基)苯基]乙 基}丙埽酿胺至含11.7 ml乙醇與2.9 ml水之混合物中,與 209·6 mg (3.01 mmol)羥基氣化錢及 399.5 mg (3.77 mmol) 152 201136518 碳酸鈉混合。反應混合物回流加熱18小時後,再與水混 合。以乙酸乙酯重複萃取後,合併之有機相經硫酸鎂脫水, 減壓蒸餾排除溶劑,殘質使用矽膠,以環己烷/乙酸乙酯作 為溶離劑進行層析法(自0%乙酸乙酯至100%乙酸乙酯之梯 度)。 產量:95.0 mg (理論值之6.3%) ]H NMR (d6-DMSO) δ = 5.87 (s, 2H), 6.15 (m, 1H), 6.93 (d, 1H), , 7.55 - 7.95 (m, 7H), 8.05 (d, 1H), 8.18 (s, 1H), 9.60 (d, 1H) 〇 HPLC-MS : logP = 2.55;質量(m/z) : 498.1 (M+H)+ 步驟2 (2E)-3-[4-(5-環丙基-1,2,4-噚二唑-3-基)-3-(三氟曱基)苯 基]-N-{2,2,2-三氟-l-[3-(三氟曱基)苯基】乙基}丙烯醯胺(表 1之化合物編號la-123)
先添加步驟 1 之 80 mg (0.16 mmol) (2E)-3-[4-(N'_羥基 曱脒基)-3-(三氟曱基)苯基]-N-{2,2,2-三氟-l-[3-(三氟曱基) 苯基]乙基}丙烯醯胺至2 ml吡啶,於室溫下與16.7 mg (0.16 mmol)環丙烧幾基氯混合,及回流加熱18小時。減 壓蒸餾排除大部份吡啶,殘質與水混合,以乙酸乙酯萃取。 153 201136518 經硫酸鎂脫水後,減壓蒸館排除溶劑,殘質經石夕膠使用環 己烷/乙酸乙酯作為溶離劑進行層析法(0%乙酸乙酯至 100%乙酸乙酯之梯度)。 產量:53.0 mg (理論值之58.5%) ]H NMR (d6-DMSO) δ = 0.78 (m, 4H), 1.49 (m, 1H), 6,18 (m, 1H), 7.03 (d, 1H), 7.70 - 7.80 (m, 3H), 7.87 (m, 2H), 7.91 (m,1H),8.04 (d, 1H), 8.18 (s,1H),9.60 (d,1H)。 HPLC-MS : logP = 4.53;質量(m/z) : 548.1 (M+H)+ 合成實例l〇(亞砜及砜依據化學式反應流程18之製法) 2-氯-N-(l,l-二氧撐基硫雜環丁 -3-基)-4-[(1Ε)-3-酮基 -3-({2,2,2-三氟-1-【3-(三氟甲基)苯基】乙基}胺基)丙-1-烯-1-基]苯曱醯胺(表1之化合物編號la-166)及2-氣-N-(l-氧撐基 硫雜環丁-3-基)-4-[(1Ε)-3-酮基-3-({2,2,2-三氟-1_[3-(三氟甲 基)苯基】乙基}胺基)丙-1-烯-1-基】苯曱醢胺(表1之化合物 編號 la-167)
先添加 100 mg (0.19 mmol) 4-[(1Ε)-3-酮基-3-({2,2,2-三氟-H3-(三氟曱基)苯基]乙基}-胺基)丙-1-烯小基]-Ν-(硫 雜環丁-3_基)-2_(三氟曱基)苯甲醯胺(化合物編號ia-i3〇,類 似合成實例2之方法合成)至5 ml二氯曱烷中,與117.8 mg 154 201136518 (〇·47 mmol)間-氣過苯甲酸溶液(含量:7〇0/〇),混合物於2〇〇c 下攪拌5小時。溶液與飽和碳酸氫鈉溶液混合,以乙酸乙 酯重複萃取。合併之古 狀, 有機相依序經硫代硫酸鈉溶液及水洗 滌,經硫酸鎂脫水,另 析。 久砘壓蒸餾排除溶劑。殘質經矽膠層 產量: 28.0 mg (26.1〇/0)) 一 0 ) 2、氣-Ν-(1,1·二氧撐基硫雜環丁 _3_ 1ηΓ^5? 〇ι m〇) 6 " 4'2° (m,2H),4·53 (m,2H),4·63 (m? 1H), 6.15 (m, 1H), 5 q〇 ίΛ •y〇 (ds 1H), 7.45 - 7.85 (m, 5H), 7.95 (m, 1H), 8.05 (s, 1H), 9 ^ y.28 (d, 1H),9.50 (d,1H)。 HPLC-MS : logP = 2.93- + 弋質量(m/z) : 555.2 (M+H)+ 19.0 mg (18.3%) 2氯也⑴氧撐基硫雜環丁-3- 基H-[(1E)·3·酮基·3你,氟小[Μ氟甲基)苯基]乙 基}胺基)丙-1-烯小基]笨曱醯胺。 !H NMR (d6-DMSO) δ ^ . 3·20 (m, 2H), 4.20 (m, 2H), 4.38 (m, 1H),4.63 (m,2H),6 is , _ 5 (m,1H), 6.90 (d,1H),7.45 - 7.85 (m,5H),7.95 (m,1H、s λ 8·〇5 (s, 1H), 9.08 (d, 1H), 9.50 (d, 1H)。 HPLC-MS : logP = 2.63-晰曰 ,TT、+ 質量(m/z) : 539.2 (M+H) 合成實例11 (通式1及1化合物依據化學式反應流程1 及7之製法) 155 201136518 步驟1 N-環丙基-6-破-4-(三1甲基)於醯胺
取ί哀丙基胺(862 mg, 15.1 mm〇i)溶於4 ml二氯甲烧, 於氬氣壓下,滴加二甲基I呂之曱苯溶液(2 m,7.55 ml,15.1 mmol)混合。混合物攪拌30分鐘,然後滴加6_碘_4_(三氟曱 2008,51,3133 - 3144經於酸g旨化合成)溶於3 二氣曱烧 中之溶液。混合物回流加熱一夜,冷卻至室溫後,小心加 水。混合物以乙酸乙醋萃取,有機相經酒石酸卸納溶液洗 滌’經硫酸鎂脫水,及過濾,濾液減壓濃縮。使用溶離劑 環己烷/乙酸乙酯(ΕΑ)(0% EA至30% EA)進行矽膠層析法純 化。 產量:288 mg (理論值之53%)。 HPLC-MS : iogP = 1.92;質量(m/z) : 357.0 (M+H)+; 4 NMR (CD3CN) 0.54 - 0.59 (m,2H),0.72 - 0.79 (m,2H), 2.79 - 2.82 (m, 1H), 7.07 (br. s, 1H), 8.11 (s, 1H), 8.48 (s, 1H)。 步驟2 (2E)-3-[5-(環丙基胺甲醯基)-4-(三氟曱基)》比啶·2-基]丙烯 酸 156 201136518 O r
取Ν'環丙基-6-蛾-4-(三氟曱基)柊醯胺(125 mg,〇 34 mmol)及(2办3<4,4,5,5_四甲基_u,2_二氧硼雜環戊·2基) 丙烯酸乙酯(93 mg,0.41 mmol)溶於2 ml 1,4-二氧雜環己 烷,於氬氣壓下,與碳酸鈉(180 mg,1.72 mmol)及雙(三環 己基膦)鈀(π)氣化物混合。反應混合物於微波爐(cem Discover)中’於12〇〇c(8〇w)下加熱1〇分鐘。然後使反應 混合物經球管過濾,濾液溶於乙酸乙酯,以鹽酸(1M)洗 滌,經硫酸鎂脫水,過濾及減壓濃縮。殘質溶於丨.5 ml乙 醇,與氫氧化鈉溶液(1M)混合,於室溫下攪拌一夜。然後 添加反應混合物至冰冷之稀鹽酸中,以乙酸乙酯萃取。有 機相經硫酸鈉脫水,過濾及減壓濃縮至乾。 產量:72 mg (理論值之70%)。
HPLC-MS : logP = 1.26;質量(m/z): 301.1 (M+H)+ ; 4 NMR (CD3CN) 0.56 - 0.58 (m, 2H), 0.76 - 0.79 (m> 2H), 2.80 -2.85 (m, 1H), 6.96 (d, 1H), 7.08 (br. s, 1H), 7.69 (d, 1H), 7.87 (s,1H),8.74 (s, 1H),9.5 (br. s,1H)。 步驟3 N-環丙基-6-[(lE)-3-酮基-3-({2,2,2-三氟-l-[3_(三氟甲基)苯 基】乙基}胺基)丙-1-稀-1-基]_4_(三氟甲基)於醯胺(表6之化 合物編號If-2) 157 201136518
先添加(2£)_3-|>(環内基胺甲醯基)_4_(三氟甲基)〇比啶 -2-基]丙烯酸(61 mg,〇.2〇咖〇1)及2,22_三氟_1[3_三氟甲 基苯基]乙胺(46 mg,〇.l9 mm〇1)至N,N_二曱基曱醯胺 中,與 HBTU(72 mg, 0·19 _〇1)及 N•甲基嗎琳(57 邮,〇 57 mmol)混合’及於室溫下攪拌一夜。隨後,反應混合物減壓 濃縮’溶於乙酸乙酯及依序以碳酸氫鈉溶液(1〇%)及飽和氯 化鈉溶液洗滌。有機相經硫酸鈉脫水,過濾及減壓濃縮。 殘質使用水/乙腈作為溶離劑進行製備性HPLC層析法(梯 度=43分鐘’自10%乙腈之水溶液至1〇〇%乙腈)。 產量:171^(理論值之16°/〇)。
HPLC-MS : logP = 3.27;質量(m/z): 526.1 (M+H)+; NMR (CD3CN) 0.56 - 0.58 (m, 2H), 0.76 - 0.78 (m, 2H), 2.81 -2.85 (m, 1H), 6.01 (quint, 1H), 7.08 (s, 1H), 7.28 (d, 1H), 7.65 - 7.68 (m, 2H), 7.76 - 7.81 (m, 3H 合成實例12(通式1-16及1-17化合物依據化學式反應流程 4、6c及17之製法) 步驟1 6-氣-1-甲基-2-({2,2,2-三氟小[3-(三氟曱基)苯基]乙基}胺 甲醯基)-1Η-吲哚-5-羧酸乙酯 158 201136518
先添加6-氣-2-({2,2,2-三氟-1·[3-(三氟曱基)苯基]乙基} 胺曱醢基)-1Η-吲哚-5-羧酸乙酯(1.30 g, 2.63 mmol)(合成實 例8,步驟3)及碳酸鉀至乙腈(39 ml)中,與碘曱烷(561 mg, 3.95 mmol)混合。反應混合物回流加熱一夜。冷卻至室溫 後,混合物減壓濃縮至乾,及殘質溶於乙酸乙酯,及以水 洗滌。有機相經硫酸鈉脫水,過濾及減壓濃縮至乾。 產量:1.14 g (理論值之85%)。 HPLC-MS : logP = 4.74;質量(m/z): 507.2 (M+H)VH NMR (CD3CN) 1.38 (t, 3H), 3.93 (s, 3H), 4.35 (q, 2H), 6.13 (quint, 1H), 7.25 (s, 1H), 7.59 (s, 1H), 7.65 - 7.69 (m, 1H), 7.77 -7.79 (m, 1H), 7.88 - 7.90 (m, 1H), 7.98 (s, 1H), 8.08 - 8.11 (m,1H),8.21 (s,1H)。 步驟2 N5-烯丙基-6-氯-1-甲基-N2-{2,2,2-三氟-1_[3_(三氟曱基)苯 基I乙基}-1Η-吲哚-2,5-二曱醯胺(表3之化合物編號Ic_32)
取烯丙基胺(156 mg,2.73 mmol)溶於3 mi二氣甲烧,及 於鼠氣壓下,添加含二曱基銘之甲笨溶液(2 μ, 1 37 ml, 159 201136518 2.73 mmol)混合。混合物攪拌30分鐘,然後滴加含6、氣 甲基-2-({2,2,2-三氟-l-[3·(三氟甲基)苯基]乙基}胺甲醯 基)-1Η-σ弓丨哚-5-羧酸乙酯(165 mg,〇.27 min〇l)之3 mi二氣甲 烷溶液。混合物回流加熱一夜,冷卻至室溫後,小心加水。 混合物經乙酸乙酯萃取’有機相經酒石酸鉀鈉溶液洗滌, 經硫酸鎂脫水’及過濾’及濾液減壓濃縮。使用溶離劑環 己烷/乙酸乙酯(EA) (0% EA至30% EA)進行矽膠層析法純 化。 產量:74 mg (理論值之52%)。
HPLC-MS: logP = 3.68;質量(m/z): 518.2 (M+H)VHNMR (d6-DMSO) 3.88 - 3.90 (m, 2H), 3.95 (s, 3H), 5.11 - 5.14 (m, 1H), 5.26 — 5.29 (m, 1H), 5.87 — 5.94 (m, 1H), 6.30 (quint, 1H), 7.42 (s, 1H), 7.71 - 7.73 (m, 1H), 7.78 (s, 1H), 7.82 -7.83 (m, 2H), 8.07 - 8.08 (m, 1H), 8.22 (s, 1H), 8.56 -8.58 (m, 1H) 9.79 (d, 1H)。 合成實例13 (通式M5化合物依據化學式反應流程6b及 20之製法) 步驟1 2-氣-N-環丙基-4-碘苯甲醯胺
160 201136518 取2氣4硬表曱酸(3.31 g,11.7 mmol)溶於乙酸乙酯 (23 ml),與一滴N,队二曱基曱醯胺及亞硫醯氣(6 96 g,59 〇 mmol)混合’及回流加熱一夜。冷卻之懸浮液減壓濃縮,及 溶於二氯甲烷(6〇mi)。溶液冷卻至〇。€,及滴加吡啶(925 mg,11.7 mmol)及環丙基胺(668 mg,u 7 mm〇i)。反應混合 物回升至至咖'及攪拌一夜。然後以鹽酸(1 M)洗滌,經硫酸 納脫水,過渡及減壓濃縮至乾。 產量·· 3.06 g (理論值之81%)。 HPLC-MS: logP = 2.13;質量(m/z): 321.9 (M+H)+; bNMR (CD3CN)0.53~〇.57(m,2H),0.72 - 0.77 (m,2H),2.77-2.83 (m,1H),6.87 (br· s,1H),7.16 (d,1H), 7.71 (d,1H), 7.84 (s,1H)。 ’ 步驟2 2_氯_N-環丙基-4-[3-酮基-3-({2,2,2-三氟-l-[3-(三氟曱基)苯 基]乙基}胺基)丙-1-快-1-基】苯甲醯胺
取2-氯-N-環丙基-4-蛾苯曱醯胺(1.0 g,3.11 mmol)^ 丙炔酸(222 mg, 3.11 mmol)溶於N,N_二曱基曱醯胺(1.2 mi) 及冷卻至0°C。然後添加雙(三苯基膦)鈀(π)二氯化物(43 mg 0.06 mmol)及碘化亞銅(1)(23 mg,0.12 mmol),混合物冷卻 161 201136518 至l〇 C。添加二異丙基胺(786 mg,7.77 mmol)後,混合物 慢慢回升至室溫及攪拌一夜。反應混合物經乙酸乙酯稀 釋’依序以鹽酸(2 M)及飽和氣化鈉溶液洗滌,經硫酸鎂脫 水’過濾及減壓濃縮至乾。殘質溶於N,N-二甲基曱醯胺(1 ml)’與4-(4,6-二甲氧基[1.3.5]三畊-2-基)-4-曱基嗎啉鏽氣 化物水合物(973 mg,3.52 mmol)及2,2,2-三氟三氟曱 基苯基]乙胺(780 mg,3.20 mmol)混合,及於室溫下檀拌— 夜。反應溶液與鹽酸(1 M)混合,以乙酸乙酯萃取。有機相 經飽和碳酸氫鈉溶液及飽和氣化鈉溶液洗滌,經硫酸鈉脫 水,過濾及減壓濃縮至乾。殘質使用溶離劑環己烷/乙酸乙 酯(ΕΑ)(0% EA至40% EA)進行矽膠層析法純化。 產量:462 mg (理論值之30%)。 HPLC-MS : logP = 3.34;質量(m/z): 489.0 (M+H)Vh NMR (CD3CN) 0.57 - 0.59 (m,2H),0.74 - 0.78 (m,2H),2.79 〜 2.86 (m, 1H), 5.94 (quint, 1H), 6.93 (s, 1H), 7.45 - 7.47 (m 1H),7.55 - 7.57 (m,1H),7.65 - 7.69 (m,2H),7.74 - 7.78 (m 1H),7.90 (s,1H),8.30 (d,1H)。 ’ 步驟3 2-氯-N-環丙基-4-[(lZ)-3-酮基-3-({2,2,2-三敗-l-[3-(三氟甲 基)苯基】乙基}-胺基)丙-1-稀-1-基】苯曱醯胺(表7之化合物 編號Ig-1) 162 201136518
F
取2-氣-N-環丙基-4-[3·酮基-3-({2,2,2-三氟-l-[3-(三氟 曱基)苯基]乙基}胺基)-丙-1-炔-1-基]苯甲醯胺(110 mg,0.20 mmol)、啥淋(1〇 mg,0.07 mmol)及紀/碳酸#5(5% Pd; 10 mg) 懸浮於曱醇,及攪拌4天,此期間每24小時再添加鈀/碳 酸鈣(3x 10 mg)。反應混合物經過球管過濾,及濾液減壓濃 縮至乾。殘質使用溶離劑環己烷/乙酸乙酯(EA) (0% EA至 50% EA)進行矽膠層析法純化。 產量:72 mg (理論值之70%)。 HPLC-MS: logP = 3.06;質量(m/z): 489.1 (M-H)_; !HNMR (CD3CN) 0.54 - 0.57 (m, 2H), 0.73 - 0.76 (m, 2H), 2.79 -2.83 (m, 1H), 5.93 (quint, 1H), 6.17 (d, 1H), 6.81 (d, 1H), 6.87 (s, 1H), 7.27 - 7.29 (m, 1H), 7.36 - 7.37 (m, 1H), 7.57 (s, 1H), 7.61 - 7.64 (m, 1H), 7.70 - 7.71 (m, 1H), 7.74 - 7.76 (m, 1H), 7.82 — 7.86 (m,2H)。 合成實例14(通式I及III-l化合物依據化學式反應流程10a 及21之製法) 步驟1 2,2-二氟-1-[3-(三氟曱基)苯基】丙炫-ΐ·_ 163 201136518
取2-丙基鎂化氯之THF溶液(1.3 M,7.5 ml)冷卻至 -15°C,與1-碘-3-(三氟曱基)苯(2.80 g,10.2 mmol)混合。反 應混合物於-15°C下攪拌1小時,回升至室溫,滴加2,2-二氟 -N-曱氧基-N_曱基丙醢胺之溶液(1.43 g,9.35 mmol;依據 Synth. Comm. 2008 (38),1940-1945製備)及混合,及於室溫 下攪拌一夜。然後添加混合物至冰冷之稀鹽酸中,以乙酸 乙酯萃取。合併之有機相經硫酸鈉脫水,及減壓濃縮。殘 質使用溶離劑環己烷/乙酸乙酯(EA) (0% EA至30% EA)進 行石夕膠層析法純化。 產量:1.19 g (理論值之53%)。 HPLC-MS : logP = 3.61; NMR (CD3CN) 1.93 (t,3H), 7.78 (t, 1H),8.02 (d, 1H),8.31 - 8.34 (m, 2H)。 步驟2 2_氯·Ν_環丙基-4-[(1Ε)·3-({2,2·二氟·1-【3-(三氟曱基)苯基] 丙基}胺基)-3-酮基丙-1-烯-1-基]苯甲醯胺(表4之化合物編 號 ld_l)
164 201136518 取含2,2-二氟-l-[3-(三氟曱基)苯基]丙烷_丨_酮(丨19 g, 4.99 mmol)之乙醇(15 ml)溶液與水(1.5 ml)、羥基胺鹽酸鹽 (695 mg,10.0 mmol)及乙酉复鈉(922 mg,11.2 mmol)混合,及 於75°C下攪拌21小時。混合物冷卻至室溫,減壓濃縮, 溶於鹽酸(1M) ’及以乙酸乙酯萃取。合併之有機相經硫酸 鈉脫水,及減壓濃縮。殘留之固體溶於四氫呋喃(15 ml), 及於氬氣下冷卻至〇°C。然後添加氫化鋰鋁(362 mg,9.08 mmol) ’先使混合物回升至室溫後,回流加熱2小時。然後 反應混合物冷卻至〇°C,先與飽和氯化銨溶液混合,以氫 氧化納>谷液(1 M)稀釋’以乙酸乙醋萃取。有機相經硫酸納 脫水,過濾及減壓濃縮至乾。殘質溶於N,N_二曱基曱醯胺 (7.5 ml)及依序與(2E)-3-[3-氯-4-(環丙基胺曱醯基)苯基]丙 烯酸(250 mg,0.94 mmol)及 4·(4,6-二曱氧基[1.3.5]三畊-2- 基)-4-曱基嗎啉鑌氯化物水合物(27〇 mg,0.97 mmol)混合, 及於室溫下攪拌一夜。反應溶液與鹽酸(1 M)混合,以乙酸 乙醋萃取。有機相經與飽和碳酸氫鈉溶液及飽和氯化鈉溶 液洗滌,經硫酸鈉脫水,過濾及減壓濃縮至乾。殘質經製 備性HPLC,使用水/乙腈作為溶離劑進行層析法(梯度=43 分鐘,自10%乙腈之水溶液至1〇〇%乙腈之梯度)。 產量:108 mg (理論值之4%)。 HPLC-MS . logP = 3.04;質量(m/z): 487」(M+H)+; iH nmr (CD3CN) 0.56 - 0.59 (m,2H),0.73 - 0.77 (m,2H),0.92 (t, 3H), 2.81 - 2.84 (m,1H),4.91 - 4.92 (m,1H), 6.65 (d,1H), 6.93 (s,1H),7.16 - 7.17 (m,1H),7 39 _ 7 42 (m,2H),7 47 _ 165 201136518 7.65 (m,6H)。 合成實例15 (通式I及II化合物依據化學式反應流程12c 之製法) 步驟1 (5_溴-2,3-二氫-1H-節-1-基)胺甲酸第三丁酯
取含 16 g (75.4 mmol) 5-漠茚滿-1-胺、12.8 g (320 mmol) 氫氧化鈉水溶液及200 ml THF之混合物於0°C下,與含32.9 g (151 mmol)二碳酸二-第三丁酯之THF溶液混合,及於0°C 下攪拌至完全轉化為止。進行萃取操作及層析純化後,產 生18 g (57.7 mmol) (5-溴-2,3-二氫-1H-茚-1-基)胺曱酸第三 丁酯(77%)。 步驟2 (2Ε)-3-{1-[(第三丁氧基羰基)胺基】-2,3-二氳-1H-節-5-基}丙 烯酸曱酯
取含25 g (80.1 mmol) (5-溴-2,3-二氫-1H-茚-1-基)胺甲 166 201136518 酸第三丁酯、975 mg (3.20 mmol)參(2-曱基笨基)膦、179 mg (797 μιηοΐ)乙酸鈀(II)及8.9 g (1〇3 mm〇l)丙烯酸曱酯之 150 ml三乙基胺混合物於150。(:下攪拌5小時。據出沉殿, 及經層析純化,產生19 g (59.9 mmol) (2Ε)_3-{1·[(第二丁氧 基幾基)胺基]-2,3-二氫-1Η-茚-5-基}丙稀酸甲g旨(75%)。 步驟3 •5-基}丙 (2Ε)-3-{1-[(第三丁氧基羰基)胺基】-2,3·二氫-1Η-節 烯酸
基)胺 取 17 g (53.6 mmol)(2E)-3-{l-[(第三丁 氧基竣 基]-2,3-二氫-111-節-5-基}丙稀酸曱酉旨於30〇1111稀^< 化鈉溶液中回流加熱1小時,濾出所得沉澱,以己齡氣氣 減壓乾燥。產生 13.6 g (44.8 mmol) (2Ε)-3-{1-[(第二 、及 羰基)胺基]-2,3-二氫-1H-茚_5_基}丙烯酸(84%)。 丁氣基 lH NMR (400MHz, d6-DMSO) δ= 1.43 (s, 9Η), 1 λ . (坩,1Η、 2.35 (m,1Η),2.77 (m,1Η),2.89 (m,1Η),4.98 (m,1Η)〜, (d,1H),7.21 (t,1H),7.48 (d,1H),7.52 (s,1H),7.56 (: 6.46 12.22 (br. s,1H)。 ’ lH), HPLC-MS : logP = 2.47;質量(m/z) : 248.1 (M爲疒 步驟4 {5-[(1Ε)·3-酮基-3-({2,2,2·三氟-l-[3-(三氟甲基)笨基 167 201136518 胺基)丙-1-稀-1-基】-2,3-二氫-1H-節_1_基}胺甲酸第三丁醋
取 1.5 g (4.95 mmol) (2Ε)-3-{1-[(第三丁氧基羰基)胺 基]-2,3-二氫-1H-茚-5-基}丙稀酸及 1.2 g (4.95 mmol) 2,2,2- 三氟-1-[3-(三氟甲基)苯基]乙胺溶於1〇〇〇11〇]^«;',添加1.5§ (5.44 mmol) 4-(4,6-二曱氧基-1,3,5-三畊-2-基)-4-甲基嗎啉 -4-鏽氯化物,加熱反應混合物至50°C—夜。反應溶液經乙 酸乙酯稀釋,以飽和NaHC03溶液、1N鹽酸及飽和氣化鈉 溶液洗滌,經硫酸鈉脫水,過濾及濃縮。經層析純化,產 生 2.3 g (4.45 mmol) {5-[(1Ε)-3-酮基-3-({2,2,2-三氟 -l-[3-(三氟曱基)苯基]乙基}胺基)丙小烯-1-基]-2,3-二氫 -1H-茚-1-基}胺曱酸第三丁酯(87%)。 !H NMR (400MHz, d6-DMSO) δ= 1.43 (s, 9Η), 1.83 (m, 1H), 2.37 (m, 1H), 2.78 (m, 1H), 2.91 (m, 1H), 4.99 (m, 1H), 6.14 (p, 1H), 6.78 d, 1H), 7.23 (m, 2H), 7.43 (m, 2H), 7.53 (d, 1H), 7.71 (t, 1H), 7.80 (d, 1H), 7.94 (d, 1H), 8.04 (s, 1H), 9.39 ppm (d,1H)。 HPLC-MS : logP = 4·44;質量(m/z) : 529.2 (Μ+Η)+· 步驟5 (2E)-3-(l-胺基-2,3-二氫-1H-茚-5-基)-N-{2,2,2-三氟 168 201136518 1-[3-(三氟曱基)苯基]乙基}丙嫜醯胺
取 2.2 g {5-[(1Ε)-3-酮基-3-({2,2,2-三氟-1-[3-(三氟曱 基)苯基]乙基}胺基)丙-1-稀-1-基]·2,3_二氫-1H-茚小基)胺 甲酸第三丁酯溶於40 ml二氧雜環己烷’與1〇 ml半飽和鹽 酸混合’及於室溫下擾摔一夜。反應混合物與水混合,以 乙酸乙酯萃取。合併之有機相經硫酸鈉脫水’過濾及濃縮。 產生 1.5 g (2Ε)-3-(1-胺基-2,3-二氫-1H-茚-5-基)-N-{2,2,2- 三氟-l-[3-(三氟曱基)苯基]乙基}_丙烯醯胺(82%)。 NMR (400MHz, d6-DMS〇) δ= 2.02 (m, 1Η), 2.49 (m, 1H), 2.92 (m, 1H), 3.09 (m, 1H), 4.74 (m, 1H), 6.15 (p, 1H), 6.78 (d, 1H), 7.52-7.67 (m, 4H), 7.71 (t, 1H), 7.82 (d, 1H), 7.97 (d, 1H),8.06 (s, 1H),8.45 (br. S, 2H),9.53 (d,1H)。 HPLC-MS : logP = 1·70;質量(m/z) : 412.2 (M-NH2)+, 步驟6 (2E)-3-(l-乙醯胺基-2,3-二氫-1H-節-5-基)-N-{2,2,2-三氟 -l-[3-(三氟甲基)苯基]乙基}丙烯醯胺(表5之化合物編號 Ie-1) 169 201136518
取 150 mg (2Ε)-3-(1-胺基-2,3-二氫-1H-節-5, 基)-N-{2,2,2-三氟-1-[3-(三氟甲基)苯基]乙基}丙稀酿胺溶 於5 ml .一氯甲烧’與71 mg N-甲基嗎琳及3 6 mg乙酸軒現 合,及於室溫下攪拌一夜。反應混合物於旋轉蒸發器上濃 縮,得到 165 mg (2Ε)-3-(1-乙醯胺基_2,3_二氫-1H-茚 基)-N-{2,2,2-三氟-1-[3-(三氟曱基)苯基]乙基}丙烯醯胺 (100%)。 !H NMR (400 MHz, d6-DMSO) : 1.78 (m, 1H), 1.87 (s, 3H), 2.40 (m, 1H), 2.82 (m, 1H), 2.93 (m, 1H), 5.27 (q, 1H), 6.14 (m, 1H), 6.80 (d, 1H), 7.24 (d, 1H), 7.44 (d, 1H), 7.48 (s, 1H), 7.54 (d, 1H), 7.71 (t, 1H), 7.81 (d, 1H), 7.95 (d, 1H), 8.05 (s, 1H),8.21 (d,1H),9.41 (d,1H)。 HPLC-MS : logP = 3.00;質量(m/z) : 471.1 (M+H)+. 合成實例16 (通式1-9及VII-3化合物依據化學式反應流程 10d及12d之製法) 步驟1 1-[4-溴-2-(三氟甲基)苯基】甲胺 170 201136518 F Br
F 於 〇°C 下慢慢添加 18ml BH3.Me2S (180 mmol,10M)至 含 10.0 g (40.0 mmol) 4-溴-2-(三氟曱基)苯基氰(Chem.
Pharm. Bull. 2005, 53, 4, 402-409)之 THF (110 ml)溶液中。 混合物於0°C下攪拌30分鐘,然後回升至25°C及攪拌30 分鐘,隨後,回流加熱混合物30分鐘。冷卻至室溫後,反 應混合物與lMNaOH水溶液混合,以乙酸乙酯(3χ 150 ml) 萃取。合併有機相’經硫酸鈉脫水,及減壓濃縮。所得粗 產物於0 ^下與之乙醇溶液混合,齡混合物^小時。 此σ物減壓’以乙鱗洗㈣體。得到9 冲· 漠-2-(三氟甲基)笨基]甲胺鹽酸鹽。 HPLC-MS 步驟2 =254.09 (M+H)+. .1〇gP = 0.92,質量(m/z): [4、臭-2-(二氟甲基)笨甲基]胺甲酸第三丁醋
由[,/臭2-(二氟曱基)苯基]曱胺鹽酸鹽與二碳酸二-t —丁酉曰類似(5冬2,3_二氮_瓜節-卜基)胺曱酸第三丁基 自°成實例15 ’步驟丨)之反應’製得[4:;臭·2_(三氟甲 基)本曱基]胺甲酸第三丁酯。 171 201136518 HPLC-MS : logP = 4.13,質量(m/z) : 297.9 (M+-C4H9)+ lH NMR (400 MHz, CD3CN) : δ = 7.83 (m, 1H), 7.78 (d, 1H), 7.45 (d, 1H),5.85 (s,1H,br),4.35 (d,2H),1.42 (s,9H)。 步驟3 (2E)-3-[4-{[(第三丁氧基羰基)胺基]甲基卜3_(三氟甲基)苯 基1丙烯酸
由[4-溴-2-(三氟甲基)苯曱基]胺曱酸第三丁酯與 (2E)-3-(4,4,5,5-四甲基-1,3,2-一敦爛雜環戊-2-基)丙稀酸乙 基酯,類似(2E)-3-[4-(環丙基胺曱醯基)_3_三氟曱基苯基]丙 烯酸(來自合成實例4,步驟3)之反應,製得(2E)_3_[4_{[(第 三丁氧基羰基)胺基]曱基}_3_(三氟甲基)苯基]丙烯酸。 HPLC-MS : logP = 2.67,質量(m/z) : 290 1 (m+_C4H9)+ NMR (400 MHz, CD3CN) : δ = 7.90 (s, 1H), 7.84 (d, 1H), 7.68 (d,1H,J=16Hz),7.57 (d,1H),6.55 (d,1H,J=16Hz), 5.83 (s, 1H, br), 4.42 (d, 2H), 1.42 (s, 9H) ° 步驟4 H-K1E)-3-酮基-3-({2,2,2-三敦-1-【3_(三氟曱基)苯基]乙基} 胺基)丙-1-稀-1-基】-2-(三氟甲基)笨甲基}胺甲酸第三丁酯 172 201136518
在含980 mg (1 eq,2.84 mmol) (2Ε)-3·[4-{[(第三丁氧基 羰基)胺基]甲基}-3-(三氟甲基)苯基]丙烯酸之1〇 ml二氣曱 烧溶液中添加481 mg (1 eq,2.84 mmol) 6-氯經基苯并三。坐 及707 mg (1.3 eq,3.70 mmol) 1-乙基-3-(3-二曱基胺基丙基) 碳化二亞胺鹽酸鹽(EDC)及733 mg (2 eq,5.68 mmol, 989 μΐ) 亨尼氏鹼(Huenig's base)。於室溫下攪拌反應混合物20分 鐘。然後添加 1.04 g (1.5 eq,4.26 mmol) 2,2,2-三氟 -l-[3-(三氟曱基)苯基]乙胺之1 ml CH2C12溶液,於室溫下授 拌混合物16小時。反應混合物減壓濃縮及分溶於飽和 Na2C〇3溶液與乙酸乙酯之間。乾燥及濃縮溶劑後,得到 2.108g {4-[(1Ε)·3·酮基-3-({2,2,2·三氟-1-[3-(三氟甲基)苯基] 乙基}胺基)丙-1-烯-1-基]-2-(三氟甲基)笨曱基}胺曱酸第三 丁酯之油狀物,其未再進一步純化即於下一個步驟中轉化。 HPLC-MS : logP = 4.40;質量(m/z) : 571.40 (M+H)+ 步驟5 (2E)-3-[4-(胺基曱基)-3-(三氟曱基)苯基】_Ν·{2,2,2_三氟 -1-[3-(三氟-曱基)苯基】乙基}丙烯醯胺
173 201136518 取2 g (1 eq,3.6 mmol) N-Boc 肉桂醯胺溶於 13.7 ml 4MHC1之二氧雜環己烷溶液(15 eq,55 mmol)及於室溫下攪 摔4小時。隨後’粗產物混合物於槽溫<3〇C3C下減壓濃縮。 所得粗產物(1.7g)未再進一步純化即 呈鹽酸鹽用於下一個 步驟。 HPLC_MS : 1〇gp = 1.6卜質量(m/z) : 471.35 (M+H)+ 步驟6 (2E)-3-{4-[(異丁醯基胺基)曱基]_3_(三氟曱基)苯 基}-义{2,2,2-三氣+叫王氟甲基)苯基】乙基}丙烯醯胺(表 1之化合物la-266)
取30 mg (1.2 eq,0.28 mmol)異丁醯氣溶於lml二氯甲 烧。在其中添加 113 mg (i.o eq,〇 24 細1〇1)(2£)-3-[4-(胺基 曱基)-3-(三氟曱基)苯基]_Nj2,2,2_三氟_1[3_(三氟曱基)苯 基]乙基}丙烯醯胺之鹽酸鹽(來自步驟5)及93 mg (3 eq)亨尼 氏鹼(Htimg'sbase)。混合物於室溫下攪拌16小時後,濃縮。 粗產物經‘備性HPLC純化(Phenomenex Gemini C18 5μιη; 125八;八9仙50父21.2111111;梯度:〇-1.5分鐘78%水、20°/〇乙 腈,1.5-10.0分鐘線性梯度至18%水、8〇0/〇乙腈,1〇 〇-14 〇〇 分鐘180/〇水、20。/〇乙腈;依2ml/min添加改質劑:ι〇〇/0 NH4HC03)。產生57 mg (44·%) (2E)·3]4-[(異丁醯基胺基) 174 201136518 曱基]-3-(三氟曱基)苯基}-Ν-{2,2,2·三氟-l-[3-(三氟-曱基) 苯基]乙基}丙烯醯胺。 HPLC-MS : logP = 3.78,質量(m/z) : 541.2 (M+H)+. 咕 NMR (400 MHz,d6-DMSO): δ = 9.48 (d,1H),8.55 (t,1H), 8.05 (s,1H),7.90 (m,2H),7.88 (d,1H),7.80 (d,1H), 7.70 (t, 1H), 7.61 (d, 1H, J=16Hz), 7.50 (d, 1H), 6.90 (d, 1H, J=16 Hz), 6.15 (m, 1H), 4.43 (d, 2H), 2.50 (m, 1H), 1.06 (d, 6H) 合成實例17 (通式1-6、II-l、III-l化合物依據化學式反應 流程11a之製法) 2,2,2-三氟-l-[3-氟-5-(三氟甲基)苯基】乙酮 步驟1
取5.00 g (20.57 mmol) 3-漠-5-氟三氟曱苯於60 ml無 水醚中攪拌。於-78°C及保護氣壓(氬氣)下滴加混合1.33 ml (20.75 mmol)第三丁基鋰溶液[亦參見三氟醯化反應:Η. K. Nair, D. M. Quinn Bioorganic & Medicinal Chemistry Letters 3(12), 2619-22 (1993); G. J. Pork 等人之 J. C/zem. 22, 993 (1957)]。隨後,反應混合物於-78°C下攪拌45分鐘後, 於-780C下,利用針筒分次滴加至含3.71 g(26.17mmol)三 氟乙酸乙酯之40 ml無水醚溶液中。然後先於-78°C下攪拌 175 201136518 所有反應混合物10分鐘,然後於室溫下攪拌丨小時。操作 時’添加所有反應混合物至水中,以越萃取。排出有機相, 於40°C下減壓乾燥(基於化合物之高揮發性,不低於1〇毫 巴)。產生4.06 g (理論值之75.9%) 2,2,2-三氟-1-[3-氟-5-(三 氟曱基)苯基]-乙酮,呈水合物單離出。 HPLC-MS : l〇gP = 2.54 ’ 質量(m/z) : 261.1 (M+H)+ 步驟2 2,2,2-三氟-l_[3-氟-5-(三氟甲基)苯基】乙酮膀
取 4.00 g (15.37 mmol) 2,2,2-三氟-l-[3-氟-5-(三氟甲基) 苯基]乙酮水合物(來自步驟1)於37.3 ml吡啶與26.9 ml乙 醇之混合物中攪拌,及於回流溫度下攪拌約18小時。冷卻 後’所有反應混合物與水混合後,減壓濃縮。殘質利用矽 膠管柱層析法純化(矽膠60 _ Merck,粒度:0.04至0,063 mm; 環己烷/丙酮梯度),得到2.18 g (理論值之51·5%) 2,2,2-三 氟-l-[3-氟-5-(三氟曱基)苯基]乙酮肟之順/反異構物混合 物。 HPLC-MS : logp = 3.17; 3.21;質量(m/z) : 275 (M)+ 步驟3 α,3-雙(三氟曱基)_5_氟苯甲胺 176 201136518
取 2.18 g (7.92 mmol) 2,2,2-三氟-l-[3-氟_5_(三氟曱基) 苯基]乙酮肟於35·4 ml異丙基醚中攪拌,與3.54 g (93.35 mmol)氫化链铭批式混合[亦參見芳基三氟乙基胺類之合成 法:DE 2723464, 1977)]。然後於回流溫度下授拌反應混合 物約3小時。操作時’反應混合物冷卻至〇〇c,小心與飽 和酒石酸溶液混合,以破壞過量氫化链銘^氣體停止激烈 釋出後’混合物與2N氫氧化鈉溶液(鹼性)混合,排除有機 相。水相再經異丙基鍵卒取2次。然後合併之水相經硫酸 鎂脫水,及於40。(:(不低於50毫巴)下減壓濃縮。產生丨.55 g (理論值之71.7%) α,3-雙(三氟曱基)_5-氟苯曱胺,其未再進 一步純化即繼續用於下一個步驟。 HPLC-MS : logP = 2.51;質量(m/z) : 262.1 (M+H)+. ]H NMR (CD3CN, 400 MHz): δ = 4.61 (q, 1H), 7.46, 7.52 (2d, 1H arom.), 7.64 (s,1H arom.)。 步驟4 7V-[a,3-雙(三氟曱基)-5-氟苯甲烷】_3-三氟甲基-4-(iV-環丙基 胺曱醯基)肉桂醯胺(表1之化合物編號la-229)
177 201136518 取 95.25 mg (0.31 mmol) (2E,Z)-3-[4-(環丙基胺甲醯 基)-3-(三氟甲基)苯基]丙烯酸(來自合成實例4,步驟3)及 α,3_雙(三氟曱基)-5-氟笨甲胺於7 ml二氯曱烷中攪拌,與 1-[雙(二甲基胺基)亞曱基]_1沒_1,2,3-三唑并-[4,5七]«比啶鏽 六氟填酸鹽3 -氧化物(hATU)及Τν,τΥ-二乙基善異丙基胺(亨 尼氏驗)混合’於室溫下攪拌3〇小時。然後所有反應混合 物經1Ν鹽酸洗滌’排出有機相,經硫酸鈉脫水。減壓濃縮 後’殘質使用矽膠進行管柱層析法2次(石夕膠60-Merck, 粒度:0.04至0.063 mm;環己烷/丙酮梯度)。產生42.3 g(理 論值之24.5〇/〇) A4cx,3-雙(三氟曱基)_5-氟苯曱烷]-3-三氟甲 基環丙基_胺曱醯基)肉桂醯胺。 HPLC-MS : logp = 3.59;質量(m/z) 543.2 (Μ)+ 合成實例18 (通式(νπ·3)化合物依據化學式反應流程i〇d 及12b之製法) 步驟1 1-(4-漠-2-氟苯基)乙胺
在含12 g 4-漠_2_氣苯基氰(60 mM)之THF(120 ml)溶 液中添加0°C之75 ml (150mM) 2 Μ曱基鎂化溴之乙醚溶 液。反應混合物於〇。(:下攪拌6小時。然後慢慢添加200ml 曱醇至反應混合物中。隨後,批式添加5.7 g (150 mM)氫硼 178 201136518 化鈉’於室溫下攪拌混合物16小時。然後減壓濃縮反應混 合物’添加200 ml水。使用2 M HC1調整pH至pH=〜卜 以氯仿萃取水溶液。隨後,使用2M NaOH調整pH至 pH=〜9 ’以氣仿萃取(2χ i〇〇mi)。合併之氣仿萃液脫水後, 減壓排除溶劑。得到7.3g (44%) 1-(4-溴-2-氟苯基)乙胺之黃 色油狀物。 ]HNMR (400MHz, CDC13) : δ= 1.39 (d, 3Η), 1.61 (s, 2H, br), 4.34 (m,1H), 7.18 (m,3H)。 步驟2 N-[l-(4-溴-2·氟苯基)乙基】丙醯胺
取61 mg (1 eq,0.24 mmol) 1-(4-溴-2-氟苯基)乙胺(來自 步驟 1)溶於4 ml二氣曱烷,添加24 mg (1.1 eq,23 μΐ, 0.264 mmol)丙醯氯及70 mg (2.2 eq,90 μΐ)亨尼氏驗。於室溫下 授拌混合物5小時後,濃縮。粗產物溶於乙酸乙酯,依序以 lx 1MHC1、lx飽和碳酸鈉溶液及水洗滌,經硫酸鎂脫水。 減壓濃縮後’所得粗產物利用石夕膠層析法純化(溶離劑:環 己烷/乙酸乙酯)。得到50 mg (67%) N-[l-(4-溴-2-氟苯基)乙 基]丙醯胺。 HPLC-MS : logP = 2.19 ’ 質量(m/z) : 276.1 (M+H)+. lU NMR (400 MHz,DMSO-d6) : δ = 8.25 (d, 1H, br), 7.46 (dd, 1H),7.39 (dd,1H),7.30 (t,1H),5.05 (m,1H),2.10 (q,2H), 179 201136518 1.31 (d,3H),0.97 (t,3H). 合成實例19 (通式(VII-4)化合物依據化學式反應流程l〇e 及12a之製法) N-[4-漠-2-(三氣曱基)苯甲基】吡啶胺
於0oC下’在含0.61 g吡啶_2_基胺甲酸第三丁酯(3.2 mmol)之1 〇 mi無水DMF溶液中批式添加〇 ! 8 g NaH (60%, 4.4 mmol),於〇。(:下攪拌混合物30分鐘,隨後,於〇°c 下添加1.1 g (3.5 mmol) 4-溴-1-(溴曱基)-2-(三氟甲基)苯 (WO2006/18725)之無水DMF(5.0 ml)。反應混合物慢慢回 升至室溫及攪拌2小時。然後與水混合,以乙酸乙酯萃取。 有機相脫水及減壓濃縮。所得粗產物利用矽膠層析法純化 (正己烷/乙酸乙酯30:1至1〇: 1),得到1.1 g (77%)受N-Boc-保護之胺。 其溶於20ml經HC1飽和之乙酸乙酯中,於室溫下攪 拌一夜。隨後’以K:2C03水溶液中和及以乙酸乙酯萃取。 脫水及排除溶劑後’得到0.8 g (75%) N-[4-溴-2-(三氟甲基) 苯曱基]吡啶-2-胺之固體。 HPLC_MS : logP = 1.57 ’ 質量(m/z) : 333.0 (Μ.Η)+· ln NMR (400 MHz, CD3CN) : δ = 7.96 (dd, 1H), 7.78 (m, 1H), 180 201136518 7.68 (m, 1H), 7.50 (d, 1H), 7.43-7.39 (m, 1H), 6.58-6.56 (m, 1H), 6.50 (d,1H),5.68 (s,1H,br),4.68 (d,2H)。 表1至7所說明本發明通式(Ia)、(Ib)、(Ic)、(Id)、(Ie)、 (If)及(Ig)化合物同樣為可依據或類似上述合成實例製得之 本發明較佳化合物。 表1
R
3 5 a 其中 R2、R4 及 R5 分別為 Η,X 為 CF3 及(R、、R3, (R6)m, A及Y分別如表1中之定義。數字2至6代表芳香環上之 位置。
No. Λ R3 (R6)m A Y HPLC- MS a); NMR (δ,ppm) b> Ia-1 3,5-Cl2 H H 4-(-NHCO-) 環丙基 HPLC-MS:logP = 3.77;質量 (m/z) : 458.1 (M+H)+; 'HNMR(d4-甲醇)0.70 (m,2H),0.92 (m,2H), 1.75 (m, 1H), 5.88 (m, 1H), 6.65 (d, 1H), 7.6 -7.7 (m, 8H). la-2 3,5-Cl2 H H 4-(-NHCO-) 2-氯°比咬-3-基 HPLC-MS : logP = 3.69;質量 (m/z) : 529.1 (M+H)+; 'HNMR (d6-DMSO) 6.02 (m, 1H), 6.72 (d, 2H), 7.55(m, 2H), 7.65 (m, 3H), 7.75 (m, 2H), 8.04 (m, 1H), 8.52 (m, 1H), 9.18 (m, 1H). la-3 3-CF3 H H 4-(-NHCO-) 曱基 HPLC-MS : logP = 2.95;質量 (m/z) : 431.1 (M+H)+; 'HNMR (d6-DMSO) 2.03 (s, 3H), 6.08 (m, 181 201136518
No. (R1)» R3 (R6)m A Y HPLC- MS a>; *H NMR (δ » ppm)b) 1H), 6.70 (d, 1H), 7.56(m, 1H), 7.65 (m, 2H), 7.73 (m, 2H), 8.04 (m, 1H), 9.25 (m, 1H). Ia-4 3-CF3 H H 3-(-NHCO·) 環丙基 HPLC-MS : logP = 3.42;質量 (m/z) : 457.0 (M+H)+; 'HNMR (d6-DMSO) 0.80 (m, 4H), 1.78 (m, 1H), 6.10 (m, 1H), 6.78 (d, 1H), 7.20(m, 1H), 7.35 (m, 1H), 7.45 (m, 2H), 7.70 (m, 1H), 7.78 (m, 1H), 7.95 (m, 1H), 8.04 (m, 1H), 9.40 (m, 1H). la-5 3-CF3 H H 3-(-NHCO-) 2-氣°比咬-3-基 參見合成實例3,步驟3 la-6 3-CF3 H H 4-(-NHCO-) 2,2,2-三氟 乙基 HPLC-MS : logP = 3.43;質量 (m/z) : 499.1 (M+H)+; 'HNMR (d6-DMSO) 4.05 (m, 2H), 6.08 (m, 1H), 6.78 (d, 1H), 7.58(m, 1H), 7.70 (m, 3H), 7.78 (m, 1H), 7.93 (m, 2H), 8.01 (m, 1H), 8.95 (m, 1H), 9.47 (m, 1H). la-7 3-CF3 H H 4-(-CONH-) 0比咬-2-基 甲基 HPLC-MS : logP = 2.45;質量 (m/z) : 508.1 (M+H)+; 'HNMR (d6-DMSO) 4.60 (m, 2H), 6.10 (m, 1H), 6.89 (d, 1H), 7.25 (m, 1H), 7.35 (m, 1H), 7.58 (m, 1H), 7.7 - 7.8 (m, 3H), 7.9 - 8.0 (m, 3H), 8.50 (m, 1H), 8.95 (m, 1H), 9.35 (d, 1H). la-8 3-CF3 H H 4-CN 參見合成實例l,步驟1 la-9 3-CF3 H 3-N〇2 4-(1沁1,2,4-三唑-1-基) HPLC-MS : logP = 3.11;質量 (m/z) : 486,1 (M+H)+; 'HNMR(d3-乙腈)6.05 (m,1H), 6·85 (d,1H),7.6 -7.90 (m, 6H), 8.02 (m, 1H), 8.21 182 201136518
No. (R*)n R3 (R6)m A Y HPLC- MS a); *H NMR (6 > ppm) b) (m,1H),8.65 (m,1H). Ia-10 3-CF3 H 3-CN 4-(lH-l,2,4-三唑-1-基) HPLC-MS : logP = 2.99;質量 (m/z) : 466.1 (M+H)+; 'HNMR(d3-乙腈)6.06 (m,1H), 6.87 (d,1H),7.6 -7.90 (m, 6H), 8.02 (m, 1H), 8.21 (m, 1H), 8.65 (m, 1H). la-11 3-CF3 H 3-CH3 4-(-CONH-) 環丙基 HPLC-MS:logP = 3.02;質量 (m/z) : 471.11(M+H)+; 1HNMR (d3-CD3CN) 7.86 (s, 1H), 7.80-7.70 (m, 3H), 7.66 (t, 1H), 7.57 (d, 1H, J= 16Hz), 7.45-7.38 (m, 2H), 7.32 (d, 1H), 6.75 (s, 1H, br), 6.69 (d, 1H, J=16Hz), 5.99 (m, 1H), 2.80 (m, 1H), 2.38 (s, 3H), 0.75 (m, 2H), 0.56 (m, 2H). la-12 3,5-Cl2 H 3-CH3 4-(-CONH-) 環丙基 HPLC-MS:logP = 3.33;質量 (mJz) : 473.03(M+H)+; 1HNMR (d3-CD3CN) 7.55-7.50 (m, 2H), 7.45-7.38 (m, 2H), 7.32 (d, 1H), 7.20 (d, 1H), 7.05 (s, 1H), 7.00 (d, 1H), 6.75 (s, 1H, br), 6.69 (d, 1H, J=16Hz), 5.90 (m, 1H), 2.80 (m, 1H), 2.38 (s, 3H), 0.75 (m, 2H), 0.56 (m, 2H). la-13 3-F H 3-CN 4-(lH-l,2,4-三唑-1-基) HPLC-MS:IogP = 2.61;質量 (m/z) : 416.1 (M+H)+; 'HNMR (d6-DMSO) 5.98 (m, 1H), 6.95 (d, 1H), 7.25 (m, 1H), 7.48 (m, 1H), 7.62 (d, 2H), 7.91 (d, 2H), 8.10 (m, 1H), 8.30 (d, 2H), 9.15 (s, 1H), 9.30 (m, 1H). la-14 4-CF3 H 3-CN 4-(111-1,2,4-三唑-1-基) HPLC-MS:IogP = 3.08;質量 (m/z) : 466.1 (M+H)+; ]HNMR 183 201136518
No. (R')n R3 (R6)m A Y HPLC- MS a); ]Η NMR (δ · ppm) b) (d6-DMSO) 6.05 (m, 1H), 6.99 (d, 1H), 7.62 (m, 1H), 7.80 (s, 2H), 7.92 (d, 1H), 7.91 (d, 2H), 8.10 (m, 1H), 8.30 (d, 2H), 9.16 (s, 1H), 9.38 (m, 1H). Ia-15 2,5-CI2 H 3-CN 4-(1沁1,2,4-三唑-1-基) HPLC-MS : logP = 3.19;質量 (m/z) : 467.1 (M+H)+; 'HNMR (de-DMSO) 6.35 (m, 1H), 6.96 (d, 1H), 7.5 - 7.6 (τη, 3H), 7.90 (d, 2H), 8.13 (d, 1H), 8.32 (d, 2H), 8.10 (m, 1H), 8.30 (d, 2H), 9.16 (s, 1H), 9.45 (m, 1H). la-16 3,5-Cl2 H 3-CN 4-(lH-l,2,4-三唑-1-基) HPLC-MS : logP = 3.33;質量 (m/z) : 467.1 (M+H)+; 'HNMR (d6-DMSO) 6.05 (m, 1H), 6.95 (d, 1H), 7.62 (d, 2H), 7.92 (m, 1H), 8.10 (m, 1H), 8.32 (d, 2H), 8.10 (m, 1H), 8.30 (d, 2H), 9.15 (s, 1H), 9.45 (m, 1H). la-17 3,4-Cl2 H 3-CN 4-(11^-1,2,4-三唑-1-基) 參見合成實例5,步驟2 la-18 3-CF3 H 3-CH3 4-(-CONH-) 2,2,2-三氟 乙基 HPLC-MS : logP = 3.56;質量 (m/z) : 513.1 (M+H)VHNMR (d6-DMSO) 2.39 (s, 3H), 4.05 (m, 2H), 6.08 (m, 1H), 6.85 (d, 1H), 7.38 (d, 2H), 7.4 - 7.6 (m, 3H), 7.70 (m, 1H), 7.78 (m, 1H), 7.90 (m, 1H), (m, 1H), 8.02 (s, 1H), 8.82 (m, 1H), 9.30 (m, 1H). la-19 3-CF3 H 3-C1 4-(-CONH-) 2,2,2-三氟 乙基 HPLC-MS : logP = 3.56;質量 (m/z) : 530.9 (M+H)+; ^NMR (de-DMSO) 4.05 (m, 2H), 6.10 (m, 1H), 6.90 (d, 1H),7.5 - 7.7 (m, 2H), 7.70 - 7.8 (m, 2H), (m, 1H), 7.90 (m, 184 201136518
No. (R\ R3 (R6)m A Y HPLC- MS a); *H NMR (δ > ppm) b) 1H), 8.00 (s, 1H), 8.98 (m, 1H), 9.35 (m, 1H). Ia-20 3,5-Cb H 3-CH3 4-C-CONH-) 2,2,2-三氟 乙基 HPLC-MS : logP = 3.90;質量 (m/z) : 513.9 (M+H)+; ^NMR (dg-DMSO) 2.40 (s, 3H), 4.05 (m, 2H), 6.04 (m, 1H), 6.82 (d, 1H), 7.40 (d, 1H), 7.48 (m, 2H), 7.68 (s, 1H), 7.72 (s, 1H), 8.82 (m, 1H), 9.25 (m, 1H). la-21 3-CF3 H 3-C1 4-(-CONH-) 0比*^-2_基 曱基 HPLC-MS :logP = 2.75;質量 (m/z) : 542.1 (M+H)+; 'HNMR (d6-DMSO) 4.54 (m, 2H), 6.10 (m, 1H), 6.90 (d, 1H), 7.25 (d, 1H), 7.42 (d, 1H), 7.5 - 7.6 (m, 2H), 7.7 - 7.8 (m, 2H) 7.90 (m, 1H), 7.98 (s, lH)8.50(m, 1H), 9.85 (m, 1H). la-22 3-CF3 H 3-CH3 4-(-CONH-) °比咬-2-基 曱基 HPLC-MS :logP = 2.65;質量 (m/z) : 522.2 (M+H)+; 'HNMR (d6-DMSO) 2.39 (s, 3H), 4.56 (m, 2H), 6.10 (m, 1H), 6.85 (d, 1H), 7.25 (d, 1H), 7.35 (m, 1H), 7.48 (m, 1H), 7.55 (m, 1H) 7.6 - 7.7 (m, 2H), 7.90 (m, 1H), 7.98 (s, 1H), 8.50 (m, 1H), 8.70 (m, 1H), 9.30 (m, 1H). la-23 3-CFs H 3-CF3 4-(-CONH-) 環丙基 HPLC-MS :logP = 3.18;質量 (m/z) : 525(M+H)+; la-24 3,5-Cl2 H 3-CF3 4-(-CONH-) 環丙基 HPLC-MS : logP = 3.5; f f (m/z): 525(M+H)+; 1H NMR (d3-CD3CN) 7.91 (s, 1H), 7.82 (d, 1H), 7.70 (m, 1H), 7.65 (d, 1H, J=16Hz), 7.55-7.50 (m, 4H), 6.90 (s, 1H, br), 6.75 (d, 1H, J=16 Hz), 5.89 (m, 1H), 2.80 (m, 1H), 0.75 (m, 2H), 0.55 (m, 2H). 185 201136518
No. (R*)n R3 (R6)m A Y HPLC- MS a); !H NMR (δ > ppm) b) Ia-25 3-CF3 CH 3 H 4-CN 參見合成實例1,步驟2 la-26 3-CF3 H 3-CH3 4-(-COO-) CH3 HPLC-MS : logP = 4.09;質量 (m/z) : 446.1 (M+H)+; 'HNMR(d3-乙腈)2.55 (s,3H),3.88 (s,3H),5.96 (m,1H), 6.75 (d,1H),7.45 (m,1H), 7.6 - 7.7 (m, 2H), 7.7 - 7.8 (m, 2H), 7.88 (s, 1H). la-27 3-CF3 H 3-CH3 4-(-COO-) H HPLC-MS :logP = 3.14;質量 (m/z) : 432.1 (M+H)+; *HNMR (d6-DMSO) 2.55 (s, 3H), 6.10 (m, 1H), 6.90 (d, 1H), 7.5 - 7.6 (m, 3H), 7.70 (m, 1H), 7.8 - 7.9 (m, 3H), 7.88 (s, 1H), 9.35 (m, 1H). la-28 3-NO2 H 3-CF3 4-C-CONH-) 3,3,3-三敗-丙院-2-基 HPLC-MS :logP = 3.83;質量 (m/z) : 558.96(M+H)+; 1HNMR (d6-DMSO) 9.17 (d, 1H), 8.52 (s, 1H), 8.35 (dd, 1H), 8.28 (s, 1H), 8.19 (d, 1H), 8.12 (d, 1H), 7.98 (d, 1H, J= 16Hz), 7.82 (t, 1H), 7.57 (d, 1H), 7.13 (d, 1H, J=16 Hz), 6.93 (q, 1H), 4.77 (m, 1H), 1.31 (d, 3H). la-29 2,6-F2 H 3-CF3 4-(-CONH-) 3,3,3-三說 丙烧-2-基 HPLC-MS :logP = 3.41;質量 (m/z) : 549.01(M+H)+; 1HNMR (d6-DMSO) 9.30 (d, 1H), 9.15 (d, 1H), 8.00 (s, 1H), 7.93 (d, 1H), 7.65 (d, 1H, J=16Hz), 7.58 (d, 1H), 7.26 (t, 2H), 7.17 (d, 1H, J=16 Hz), 6.29 (m, 1H), 4.77 (m, 1H), 1.31 (d, 3H). la-30 3-CF3 H 3-CF3 4-(-CONH-) 3,3,3-三氟 丙烧-2-基 HPLC-MS : logP = 3.58;質量 (m/z) : 580.97(M+H)+; 1HNMR 186 201136518
No. (R')n R3 (R6)m A Y HPLC- MS a); ΧΗ NMR (δ > ppm) b) (d6-DMSO) 9.53 (d, 1H), 9.16 (d, 1H), 8.05 (d, 1H), 7.96 (t, 1H), 7.81 (d, 1H), 7.72 (t, 1H), 7.67 (d, 1H, J=16Hz), 7.57 (d, 1H), 6.98 (d, 1H, J=16 Hz), 6.16 (m, 1H), 4.77 (m, 1H), 1.31 (d, 3H). Ia-31 3-CF3 H 3-CF3 4-(-CONH-) 苯曱基 HPLC-MS:logP = 3.68;質量 (m/z) : 575.94(M+H)+; 1HNMR (d6-DMSO) 9.52 (d, 1H), 9.07 (t, 1H), 8.05 (s, 1H), 8.02 (s, 1H), 7.94 (m, 2H), 7.81 (d, 1H), 7.72 (t, 1H), 7.66 (d, 1H, J=16Hz), 7.61 (d, 1H), 7.35 (m, 4H), 7.28 (m, 1H), 6.96 (d, 1H, J=16 Hz), 6.15 (m, 1H), 4.44 (d, 2H). la-32 3,4-Cl2 H 3-CF3 4-(-CONH-) °比咬-2-基 甲基 HPLC-MS:logP = 2.98;質量 (m/z) : 575.97(M+H)+; 1HNMR (d6-DMSO) 9.45 (d, 1H), 9.15 (t, 1H), 8.53 (d, 1H), 8.03 (s, 1H), 7.96 (m, 2H), 7.70-7.60 (m, 3H), 7.60-7.50 (m, 3H), 7.39 (d, 1H), 7.29 (dd, 1H), 6.96 (d, 1H, J=16 Hz), 6.09 (m, 1H), 4.54 (d, 2H). la-33 3-N〇2 H 3-CF3 4-C-CONH-) 。比咬-2-基 曱基 HPLC-MS:logP = 2.93;質量 (m/z) : 553.99(M+H)+; 1HNMR (d6-DMSO) 9.17 (t,1H), 8.53 (m, 2H), 8.35 (dd, 1H), 8.27 (s, 1H), 8.19 (d, 1H), 8.12 (d, 1H), 7.98 (d, 1H, J= 16Hz), 7.85-7.80 (m, 3H), 7.68 (d, 1H), 7.39 (d, 1H), 7.29 (dd, 1H), 7.13 (d, 1H, J-16 Hz), 6.93 (q, 1H), 4.54 (d, 2H). la-34 4-N〇2 H 3-CF3 4-(-CONH-) 。比咬-2-基 甲基 HPLC-MS : logP = 2.93;質量 (m/z) : 553.99(M+H)+; 1HNMR 187 201136518
No. (R')n R3 (R6)m A Y HPLC- MS a); NMR (δ « ppm) b) (d6-DMSO) 9.17 (t, 1H), 8.53 (m, 1H), 8.35 (m, 2H), 8.27 (s, 1H), 8.19 (d, 1H), 8.00-7.90 (m, 3H), 7.80 (t, 1H), 7.69 (d, 1H), 7.39 (d, 1H), 7.29 (dd, 1H), 7.12 (d, 1H, J=16 Hz), 6.88 (q, 1H), 4.54 (d, 2H). Ia-35 2,6-F2 H 3-CF3 4-(-CONH-) 0比0定-2-基 甲基 HPLC-MS : logP = 2.46;質量 (m/z) : 544.02(M+H)+; 1HNMR (d6-DMSO) 9.29 (d, 1H), 9.14 (t, 1H), 8.52 (d, 1H), 7.99 (s, 1H), 7.93 (d, 1H), 7.80 (t, 1H), 7.70 (m, 1H), 7.65 (m, 1H), 7.39 (d, 1H), 7.25 (m, 2H), 7.17 (d, 1H, J=16 Hz), 6.29 (m, 1H), 4.54 (d, 2H). la-36 3-CF3 H 3-CFs 4-(-CONH-) °比咬-2·基 曱基 HPLC-MS : logP = 2.75;質量 (m/z) : 576.04(M+H)+; la-37 3,4-Cl2 H 3-CF3 4-C-CONH-) 環丙基 HPLC-MS : logP:3.41;質量 (m/z) : 524.93(M+H)+; la-38 2,6-F2 H 3-CF3 4-(-CONH-) 環丙基 HPLC-MS : logP = 2.89;質量 (m/z) : 493(M+H)+; 1HNMR (d6-DMSO) 9.27 (d, 1H), 8.54 (d5 1H), 7.96 (s, 1H), 7.88 (d, 1H), 7.65 (d, 1H, J=16Hz), 7.58 (d, 1H), 7.26 (t, 2H), 7.17 (d, 1H, J=16 Hz), 6.29 (m, 1H), 2.78 (m, 1H), 0.70 (m, 2H), 0.50 (m, 2H). la-39 3-CFs, 5-C1 H 3-CH3 4-(-CONH-) 環丙基 HPLC-MS : logP:3.47;質量 (m/z) : 506.98(M+H)+; 1HNMR (d6-DMSO) 9.45 (d, 1H), 8.30 (d, 1H), 8.11 (s, 1H), 8.08 (s, 1H), 8.00 (s, 1H), 7.52 (d, 1H, J=16Hz), 188 201136518
No. (R^n R3 (R6)m A Y HPLC- MS a); *H NMR (δ · ppm) b) 7.50-7.45 (m, 2H), 7.32 (d, 1H), 6.81 (d, 1H, J-16 Hz), 6.25 (m, 1H), 2.82 (m, 1H), 0.70 (m, 2H), 0.50 (m, 2H). Ia-40 3-CF3, 5-C1 H 3-CF3 4-(-CONH-) 環丙基 參見合成實例4,步驟4 la-41 3-CF3 H 3-Br 4-(-CONH-) D比咬-2-基 曱基 HPLC-MS : logP = 2.76;質量 (m/z) : 587.1 (M+H)+; 'HNMR(d6-乙腈)4.63 (m,2H), 5.95 (m, 1H), 6.73 (d, 1H), 7.22 (m, 1H), 7.35 (m, 1H), 7.9 - 8.0 (m, 6H), 8.50 (m, 1H), 8.52 (in, 1H). la-42 3-CF3 H 3-Br 4-(-CONH-) 環丙基 HPLC-MS : logP = 3.23;質量 (m/z) : 536.1 (M+H)+; 'HNMR(d6-乙腈)0.55 (m,2H), 0.75 (m, 2H), 2.71 (m, 1H), 6.00 (m, 1H), 6.70 (d, 1H), 7.40 (m, 1H), 7.5 - 7.7 (m, 6H), 9.18 (m, 1H). la-43 3-CF3 H 3-C1 4-(-CONH-) 環丙基 HPLC-MS : logP = 3.22;質量 (m/z) : 491.1 (M+H)VHNMR (de-DMSO) 0.55 (m, 2H), 0.70 (m, 2H), 2.85 (m, 1H), 6.10 (m, 1H), 6.80 (d, 1H), 7.40 (m, 1H), 7.58(m, 1H), 7.70 (m, 1H), 7.80 (m, 1H), 7.90 (m, 1H), 8.01 (m, 1H), 8.30 (s, 1H), 9.33 (m, 1H). la-44 3-CF3 H 3-C1 4-CN HPLC-MS : logP = 3.91;質量 (m/z) : 433.0 (M+H)+; ]HNMR (d6-DMSO) 6.08 (m, 1H), 6.86 (d, 1H), 7.50(m, 2H), 7.59 (m, 1H), 7.70 (m, 2H), 7.90 (m, 1H), 8.02 (m, 1H), 9.34 (m, 1H). la-45 3-CF3 H 3-Br 4-(-CONH_) 2,2,2-三氟 乙基 HPLC-MS : logP = 3.60;質量 (m/z) : 577.1 (M+H)VHNMR (d6-DMSO) 4.05 (m, 2H), 6.10 (m, 189 201136518
No. (R\ R3 (R6)m A Y HPLC- MSa); *Η NMR (δ · ppm)b) 1H),6.90 (d,1Η),7·5 - 7.7 (m,2H), 7.70 - 7.8 (m, 2H), (m, 1H), 7.90 (m, 1H), 8.00 (s, 1H), 8.98 (m, 1H), 9.35 (m, 1H). Ia-46 3-CF3 H 3-CF3 4-CN HPLC-MS:logP = 4.06;質量 (m/z) : 466.0 (M+H)+; 'H NMR (d6-DMSO) 6.09 (m, 1H), 6.88 (d, 1H), 7.50(m, 2H), 7.59 (m, 1H), 7.70 (m, 2H), 7.90 (m, 1H), 8.02 (m, 1H), 9.33 (m, 1H). la-47 3-CF3 H 3-CFa 4-(-CONH-) 2-(2,2,2-三 氟-乙氧基) 乙基 HPLC-MS : logP = 3.58;質量 (m/z) : 611.03(M+H)+; 1HNMR (d6-DMSO) 9.53 (d, 1H), 8.65 (t, 1H), 8.05 (s, 1H), 8.00 (s, 1H), 7.94 (m, 2H), 7.80 (d, 1H), 7.71 (t5 1H), 7.65 (d, 1H, J=16Hz), 7.54 (d, 1H), 6.97 (d, 1H, J=16 Hz), 6.16 (m, 1H), 4.11-4.04 (q, 2H, J(H,F)= 19Hz, J(H,H)=10 Hz), 3.70 (t, 2H), 3.40 (t, 2H). la-48 3-CF3 H 3-CFa 4-(-CONH-) 4-氟苯基 HPLC-MS : logP = 3.89;質量 (m/z) : 578.99(M+H)+; 1HNMR (d6-DMSO) 10.63 (s, 1H), 9.53 (d, 1H), 8.08 (s, 1H), 8.06 (s, 1H), 8.01 (d, 1H), 7.95 (d, 1H), 7.80 (d, 1H), 7.78-7.65 (m, 5H), 7.20 (t, 2H), 6.99 (d, 1H, J=16Hz), 6.16 (m, 1H). la-49 3-CF3 H 3-CF3 4-(-CONH-) °比咬-4-基 甲基 HPLC-MS : logP = 2;質量(m/z): 575.97(M+H)+; 1HNMR (d6-DMSO) 9.53 (d, 1H), 9.17 (t, 1H), 8.53 (d, 2H), 8.05 (s, 1H), 8.03 (s, 1H), 7.95 (m, 2H), 7.80 (m, 1H), 7.72-7.65 (m, 3H), 7.34 (d, 2H), 6.98 (d, 1H, J=16 Hz), 6.17 (m, 1H), 4.47 190 201136518
No. (R')n R3 (R6)m A Y HPLC- MS a); 4 NMR (δ,卯 m) b) (d, 2H). Ia-50 3-CF3 H 3-CF3 4-(-CONH-) °比咬-3-基 曱基 HPLC-MS:logP = 2.23;質量 (m/z) : 575.97(M+H)+; 1HNMR (d6-DMSO) 9.53 (d,1H),9.12 (t, 1H), 8.55 (d, 1H), 8.47 (dd, 1H), 8.05 (s, 1H), 8.02 (s, 1H), 7.95 (m, 2H), 7.80 (d, 1H), 7.75-7.60 (m, 4H), 7.38 (dd, 1H), 6.97 (d, 1H, J=16 Hz), 6.17 (m, 1H), 4.47 (d, 2H). la-51 3-CF3 H 3-CFs 4-(-CONH-) 2,2-雙曱氧 基-乙基 HPLC-MS:logP = 3.18;質量 (m/z) : 573.11(M+H)+; 1HNMR (d6-DMSO) 9.52 (d,1H),8.65 (t, 1H), 8.05 (s, 1H), 8.00 (s, 1H), 7.95 (m,2H), 7.80 (d, 1H),7.70 (t,1H), 7.68 (d, 1H, J=16Hz), 7.53 (d, 1H), 6.96 (d, 1H, J=16 Hz), 6.16 (m, 1H), 4.47 (t, 1H). la-52 3-CF3 H 3-CFs 4-(-CONHC Hr) 四氫呋喃 -2-基 HPLC-MS : IogP = 3.27;質量 (m/z) : 568.98(M+H)+ la-53 3-CFs H 3-CFs 4-(-CONH-) 0比咬-3-基 HPLC-MS : logP = 2.76;質量 (m/z) : 561.99(M+H)+ la-54 3-CF3 H 3-CFj 4-(-CONH-) °比咬-2-基 HPLC-MS : logP = 3.58;質量 (m/z) : 561.99(M+H)+; 1HNMR (d3-CD3CN) 9.15 (s, 1H, br), 8.31 (d, 1H), 8.20 (d, 1H), 7.98 (s, 1H), 7.90-7.75 (m, 5H), 7.65 (m, 2H), 7.15 (dd, 1H), 6.82 (d, 1H, J=16Hz), 6.02 (m, 1H). la-55 3-CFs H 3-CF3 4-(-CONH-) 2-曱氧基丙 院-2-基 HPLC-MS : logP = 3.37;質量 (m/z) : 557.01(M+H)+; 1HNMR (d6-DMSO) 9.51 (d, 1H), 8.41 (t, 191 201136518
No. (R')n R3 (R6)m A Y HPLC- MS a); 'H NMR (δ > ppm)b) 1H), 8.05 (s, 1H), 7.99 (s, 1H), 7.94 (m, 2H), 7.80 (d, 1H), 7.72 (t, 1H), 7.65 (d, 1H, J=16Hz), 7.52 (d, 1H), 6.96 (d, 1H, J=16 Hz), 6.17 (m, 1H), 4.11 (m, 1H), 3.40-3.30 (m, 5H), 1.10 (d, 3H). Ia-56 3-CF3 H 3-CF3 4-(-CONH-) 1-環丙基乙 基 HPLC-MS:logP = 3.77;質量 (m/z) : 553.04(M+H)+; 1HNMR (d6-DMSO) 9.51 (d, 1H), 8.45 (d, 1H), 8.05 (s, 1H), 8.00 (s, 1H), 7.95 (m, 2H), 7.80 (d, 1H), 7.70 (t, 1H), 7.68 (d, 1H, J=16Hz), 7.53 (d, 1H), 6.96 (d, 1H, J=16 Hz), 6.17 (m, 1H), 3.46 (m, 1H), 1.18 (d, 3H), 0.90 (m, 1H), 0.50-0.20 (m, 4H). Ia-57 3-CF3 H 3-CF3 4-(-CONH-) 2,2-二氟乙 基 HPLC-MS:logP = 3.48;質量 (m/z) : 549.1(M+H)+. la-58 3-CF3 H 3-CF3 4-(-CONH-) 2-曱氧基乙 基 HPLC-MS : logP=3.12;質量 (m/z) : 542.99(M+H)+; 1HNMR (d6-DMSO) 9.52 (d, 1H), 8.59 (t, 1H), 8.05 (s, 1H), 7.99 (s, 1H), 7.94 (m, 2H), 7.80 (d, 1H), 7.71 (t, 1H), 7.63 (d, 1H, J=16Hz), 7.54 (d, 1H), 6.96 (d, 1H, J=16 Hz), 6.16 (m, 1H), 3.45-3.30 (m, 7H). la-59 3-CF3 H 3-CF3 4-(-CONH-) 氧雜環丁 -3-基 HPLC-MS : logP = 2.89;質量 (m/z) : 540.98(M+H)+. la-60 3-CF3 H 3-CF3 4-(-CON(C h3)·) 環丙基 HPLC-MS:logP = 3.62;質量 (m/z) : 538.98(M+H)+; 1HNMR (d6-DMSO) 9.51 (d, 1H), 8.05 (s, 1H), 8.02 (s, 1H), 7.94 (m, 2H), 7.80 (d, 1H), 7.71 (t, 1H), 7.65 (m, 2H), 6.97 (d, 1H, J=16 Hz), 6.16 (m,1H), 192 201136518
No. (R\ R3 (R6)m A Y HPLC- MS a); NMR (δ > ppm) b) 3.00 (s, 3H), 2.65 (m, 1H), 0.80-0.70 (m, 2H), 0.50 (m, 2H). Ia-61 3-CF3 H 3-CF3 4-(-CONH-) 環丁基 HPLC-MS:logP = 3.58;質量 (m/z) : 538.99(M+H)+; 1HNMR (d6-DMSO) 9.50 (d, 1H), 8.72 (d, 1H), 8.02 (s, 1H), 8.00-7.85 (m, 3H), 7.80 (d, 1H), 7.70 (t, 1H), 7.68 (d, 1H, J=16Hz), 7.56 (d, 1H), 6.96 (d, 1H, J=16 Hz), 6.17 (m, 1H), 4.34 (m, 1H), 2.23 (m, 2H), 2.00 (m, 2H), 1.68 (m, 6H) · la-62 3-CF3 H 3-CF3 4-(-CONH-) 異丙基 HPLC-MS:logP = 3.41;質量 (m/z) : 526.99(M+H)+; 1HNMR (d6-DMSO) 9.51 (d, 1H), 8.37 (d, 1H), 8.05 (s, 1H), 7.99 (s, 1H), 7.95 . (m, 2H), 7.80 (d, 1H), 7.70 (t, 1H), 7.68 (d, 1H, J=16Hz), 7.53 (d, 1H), 6.96 (d, 1H, J=16 Hz), 6.16 (m, 1H), 4.02 (m, 1H), 1.13 (d, 6H). la-63 3-CF3 H 3-CF3 4-(-CONH-) 丙-2-快-1_ 基 HPLC-MS:logP = 3.36;質量 (m/z) : 523.1(M+H)+; la-64 3-CF3 H 3-CFs 4-(-CONH-) 乙基 HPLC-MS:logP = 3.18;質量 (m/z) : 512.97(M+H)+; la-65 3-CF3 H 3-CF3 4-(-CONH-) 2-氟環丙基 HPLC-MS:logP = 3.33;質量 (m/z) : 543.10(M+H)+; la-66 3-CF3 H 3-CF3 4-(-CONH-) 2·氯0比咬-4-基甲基 HPLC-MS:logP = 3.41;質量 (m/z) : 609.95(M+H)+; 1HNMR (d6-DMSO) 9.53 (d, 1H), 9.20 (t, 1H), 8.38 (d, 1H), 8.05 (s, 2H), 7.96 (m, 2H), 7.81 (d, 1H), 7.70 (m, 3H), 193 201136518
No. (R!)n R3 (R6)m A Y HPLC- MS a); JH NMR (δ > ppm)b) 7.44 (s, 1H), 7.37 (d, 1H), 6.98 (d, 1H, J=16 Hz), 6.16 (m, 1H), 4.50 (d, 2H). Ia-67 3-CF3 H 3-CFs 4_(_CON(環 丙基)-) 四氫-2H-娘 读-4-基 HPLC-MS:logP = 3.77;質量 (m/z) : 609.05(M+H)+; la-68 3-CFj H 3-CF3 4-(-CONH-) 1-乙氧基環 -丙基 HPLC-MS:logP = 3.52;質量 (m/z) : 569.04(M+H)+; 1HNMR (d6-DMSO) 9.52 (d, 1H), 9.37 (s, 1H), 8.05 (s, 1H), 8.00 (s, 1H), 7.93 (m, 2H), 7.80 (d, 1H), 7.72 (t, 1H), 7.65 (d, 1H, J=16Hz), 7.56 (d, 1H), 6.96 (d, 1H, J=16 Hz), 6.16 (m, 1H), 3.60 (q, 2H), 1.10 (t, 3H), 1.08 (m, 2H), 0.86 (m, 2H). la-69 3-CF3 H 3-CFs 4-(-CONH-) 四氫·2Η· 口底 味-4-基 HPLC-MS : logP = 3.12;質量 (m/z) : 569.04(M+H)+; 1HNMR (d6-DMSO) 9.51 (d, 1H), 8.51 (d, 1H), 8.05 (s5 1H), 8.00 (s, 1H), 7.94 (m, 2H), 7.81 (d, 1H), 7.71 (t, 1H), 7.65 (d, 1H, J=16Hz), 7.55 (d, 1H), 6.96 (d, 1H, J=16 Hz), 6.17 (m, 1H), 3.96 (m, 1H), 3.90 (m, 2H), 3.50 (m, 2H), 1.76 (m, 2H), 1.50 (m, 2H). la-10 3-CFs H 3-CFs 4-(-CONH-) 1-(°比咬-2-基)-環丙基 HPLC-MS : logP = 3.23;質量 (m/z) : 602.06(M+H)+; 1HNMR (d6-DMSO) 9.53 (d, 1H), 9.32 (s, 1H), 8.45 (d, 1H), 8.05 (m, 2H), 8.00-7.90 (m, 3H),7.80-7-65 (m, 4H), 7.51 (d, 1H), 6.99 (d, 1H, J=16 Hz), 6.17 (m, 1H), 1.55 (m, 2H), 1.23 (m, 2H). 194 201136518
No. R3 (R6)m A Y HPLC- MS a); 'H NMR (δ « ppm) b) Ia-71 3-CF3 H 3-CF3 4-(-CONH-) 2-苯基環丙 基 HPLC-MS : logP = 4_22;質量 (m/z) : 601.1(M+H)+; la-72 3-CF3 H 3-CF3 4-(-CONH-) 6-氯°比咬-3-基 HPLC-MS :logP = 3.73;質量 (m/z) : 595.95(M+H)+; 1HNMR (d6-DMSO) 10.99 (s, 1H), 9.58 (d5 1H), 8.68 (d, 1H), 8.17 (dd, 1H), 8.06 (s, 1H), 8.00 (m, 2H), 7.95 (m, 1H), 7.80 (m, 2H), 7.72 (m, 3H), 7.55 (d, 1H), 7.03 (d, 1H, J=16 Hz), 6.15 (m, 1H). la-73 3-CF3 H 3-CF3 4-(-CONH-) 5-氟°比咬-2- 基 HPLC-MS :logP = 3.31;質量 (m/z) : 593.99(M+H)+; 1HNMR (d6-DMSO) 9.52 (d, 1H), 9.04 (t, 1H), 8.40 (d, 1H), 8.05 (s, 1H), 8.00 (s, 1H), 7.94 (m, 2H), 7.81 (d, 1H), 7.70-7.63 (m, 3H), 7.43 (m, 1H), 6.98 (d, 1H, J=16 Hz), 6.16 (m, 1H), 4.61 (d, 2H). la-74 3-CF3 H 3-CFs 4-(-CONH-) 2-氟苯基曱 基 HPLC-MS : logP = 3.77;質量 (m/z) : 593(M+H)+; 1HNMR (d6-DMSO) 9.53 (d, 1H), 9.07 (t, 1H), 8.05 (s, 1H), 8.01 (s, 1H), 7.95 (m, 2H), 7.81 (d, 1H), 7.73-7.60 (m, 4H), 7.42 (t, 1H), 7.34 (m, 1H), 7.18 (m, 1H), 6.97 (d, 1H, J=16 Hz), 6.16 (m, 1H), 4.48 (d, 2H). la-75 3-CF3 H 3-CF3 4-(-CONH-) 1-氟丙烷-2-基 參見合成實例2,步驟3 la-76 3-CF3 H 3-CFs 4-(-CONH-) 1-曱基-1H-咪唾-4-基 HPLC-MS :logP= 1.72;質量 (m/z) : 579(M+H)+; 1HNMR (d6-DMSO) 9.52 (d, 1H), 8.82 (t, 195 201136518
No. R3 (R6)m A Y HPLC- MSa); 'H NMR (δ * ppm) b) 1H), 8.05 (s, 1H), 7.99 (s, 1H), 7.93 (m, 2H), 7.81 (d, 1H), 7.71 (t, 1H), 7.65 (d, 1H, J=16Hz), 7.57 (d, 1H), 7.52 (s, 1H), 6.98 (s, 1H), 6.96 (d, 1H, J=16 Hz), 6.16 (m, 1H), 4.28 (d, 2H), 3.62 (s, 3H). la-77 3-CF3 H 3-CFs 4-(-CONH-) 2-(三氟曱 基)環戊基 HPLC-MS : logP = 3.93;質量 (m/z) : 620.98(M+H)+; 1HNMR (d6-DMSO) 9.53 (d, 1H), 8.65 (d, 1H), 8.05 (s, 1H), 8.00 (s, 1H), 7.96 (m, 2H), 7.81 (d, 1H), 7.71 (t, 1H), 7.65 (d, 1H, J=16Hz), 7.43 (d, 1H), 6.95 (d, 1H, 3=16 Hz), 6.17 (m, 1H), 4.64 (m, 1H), 2.95 (m, 1H), 1.93 (m, 2H), 1.83 (m, 2H), 1.00 (m, 2H). la-78 3-CF3 H 3-CF3 4-(-CONH-) 環丙基甲基 HPLC-MS:logP = 3.52;質量 (m/z) : 539(M+H)+; la-79 3-CF3 H 3-CF3 4-(-CONH-) 2,2-二氟^丙 基 HPLC-MS : logP = 3.65;質量 (m/z) : 563.1(M+H)+; la-80 3-CF3 H 3-CF3 4-(-CONH-) (6-氣°比咬 -3-基)曱基 HPLC-MS :logP = 3.65;質量 (m/z) : 610(M+H)+; la-81 3- CFs, 4- COO ch3 H 3-CF3 4-(-CONH-) 環丙基 HPLC-MS :logP = 3.09;質量 (m/z) : 583.09(M+H)+ la-82 3-C1, 5-CF3 H 3-CF3 4-(-CONH-) 。比咬-2·基 HPLC-MS :logP = 4.32;質量 (m/z) : 596.0(M+H)+ la-83 3-CF3 H 3-CH3 4-(-CONH-) 氧雜環丁 -3-基 HPLC-MS :logP = 2.69 質量 (m/z) : 487.1(M+H)+; 196 201136518
No. (R!)n R3 (R6)m A Y HPLC- MS a); !H NMR (δ > ppm) b) Ia-84 3-CF3 H 3-CF3 4-(-CONH-) °比咬-4-基 HPLC-MS : logP= 1.99 質量 (m/z) : 562.2(M+H)+; la-85 3-CF3 H 3-CH3 4-(-CONH-) 1-乙氧基環 丙基 HPLC-MS : logP = 3.27 質量 (m/z) : 515.2(M+H)+; la-86 3-CF3 H 3-CH3 4-(-CONH-) 四氫-2H-口底 喊-4-基 HPLC-MS : logP = 2.89 質量 (m/z) : 515.2(M+H)+; la-87 3-CF3 H 3-CHs 4-(-CONH-) 5-氟°比啶-2- 基曱基 HPLC-MS :logP = 3.13 質量 (m/z) : 540.2(M+H)+; la-88 3-CF3 H 3-CH3 4-(-CONH-) 0比^^-4-基 HPLC-MS :logP= 1.87 質量 (m/z) : 508.2(M+H)+; la-89 3-CF3 H 3-Br 4-(-CON(C H3)-) 。比咬-2·基 HPLC-MS : logP = 3.47 質量 (m/z) : 586.4(M+H)+; la-90 3-CF3 H 3-Br 4-(-CONH-) 5-氟°比咬-2- 基甲基 HPLC-MS:logP = 3.23 質量 (m/z) : 606.1(M+H)+; la-91 3-CF3 H 3-Br 4-(-CONH-) 吡啶-4-基 HPLC-MS : logP= 1.96 質量 (m/z) : 574.1(M+H)+; la-92 3-CF3 H 3-Br 4-(-CONH-) 。比咬-2-基 HPLC-MS : logP = 3.47 質量 (m/z) : 574.1(M+H)+; la-93 3-CF3 H 3-Br 4-(-CONH-) 1-環丙基乙 基 HPLC-MS : logP = 3.42 質量 (m/z) : 565.1(M+H)+; la-94 3-CF3 H 3-Br 4-(-CONH-) 氧雜環丁 -3-基 HPLC-MS : logP = 2.8 質量(m/z): 553.1(M+H)+; 197 201136518
No. (R^n R3 (R6)m A Y HPLC- MS a); *H NMR (δ > ppm)b) Ia-95 3-CF3 H 3-Br 4-(-CON(C H3)-) 環丙基 HPLC-MS:logP = 3.58 質量 (m/z) : 551.1(M+H)+; la-96 3-CFs H 3-C1 4-(-CONH-) 1·乙氧基環 丙基 HPLC-MS:logP = 3.47 質量 (m/z) : 535.2(M+H)+; la-97 3-CF3 H 3-C1 4-(-CONH-) 四氫-2H-娘 喃-4-基 HPLC-MS ·· logP = 2.99 質量 (m/z) : 535.2(M+H)+; la-98 3-CF3 H 3-C1 4-(-CONH-) °比咬-2-基 HPLC-MS : logP = 3.47 質量 (m/z) : 528.2(M+H)+; la-99 3-CFs H 3-CHs 4-(-CONH-) 4-氟苯基 HPLC-MS :logP = 3.78 質量 (m/z) : 525.1(M+H)+; la-100 3-CF3 H 3-CHs 4-(-CONH-) 2,2-二說乙 基 HPLC-MS :logP = 3.13 質量 (m/z) : 495.1(M+H)+; la-101 3-CF3 H 3-CHs 4-(-CONH-) 環丁基 HPLC-MS :logP = 3.53 質量 (m/z) : 485.1(M+H)+; la-102 3-CFs H 3-CH3 4-(-CONH-) 異丙基 HPLC-MS : logP = 3.27 質量 (m/z) : 473.2(M+H)+; la-103 3-CF3 H 3-Br 4-(-CONH- N(COOCH3 )-) 甲棊 HPLC-MS :logP = 2.89 質量 (m/z) : 584.0(M+H)+; la-104 3-CF3 H 3-Br 4-(-CONH-) 2,2·二氟乙 基 HPLC-MS:logP = 3.23 質量 (m/z) : 561.0(M+H)+; la-105 3-CFa H 3-Br 4-(-CONH-) 1-丙快-2-基 HPLC-MS :logP = 3.09 質量 (m/z) : 535.0(M+H)+; la-106 3-CF3 H 3-C1 4-(-CONH-) 2-_基派咬 -3-基 HPLC-MS :logP = 2.61 質量 (m/z) : 548.1(M+H)+; 198 201136518
No. (R!)n R3 (R6)m A Y HPLC- MS a); 'Η NMR (δ « ppm) b) Ia-107 3-CF3 H 3-C1 4-(-CONHC H2CONH-) 2,2,2-三氟 乙基 HPLC-MS:logP = 2.99 質量 (m/z) : 590.1(M+H)+; la-108 3-CF3 H 3-C1 4-(-CONHC H2CON(CH 3)-) 曱基 HPLC-MS:logP = 2.72 質量 (m/z) : 536.1(M+H)+; la-109 3-CF3 H 3-C1 4-(-CONH- N(COOCH3 )-) Η HPLC-MS:logP = 2.72 質量 (m/z) : 524.1(M+H)+; la-110 3-CFs H 3-C1 4-(-CONH-) 5-氟吡啶-2-基甲基 HPLC-MS:logP = 3.42 質量 (m/z) : 546.1(M+H)+; la-111 3-CF3 H 3-C1 4-(-CONH-) 2,2-二氣丙 基 HPLC-MS:logP = 3.37 質量 (m/z) : 529.1(M+H)+; la-112 3-CF3 H 3-Cl 4-(-CONH-) 1-氣丙烧-2-基 HPLC-MS:logP = 3.25 質量 (m/z) : 511.1(M+H)+; la-113 3-CF3 H 3-C1 4-(-CONH-) 。比咬-4-基 HPLC-MS:logP=1.92 質量 (m/z) : 528.2(M+H)+; la-114 3-CFs H 3-C1 4-(-CONH-) 1-環丙基乙 基 HPLC-MS:logP = 3.68 質量 (m/z) : 519.2(M+H)+; la-115 3-CFs H 3-CH3 4-(-CONH-) 2-環丙基乙 基 HPLC-MS:logP = 3.61 質量 (m/z) : 499.2(M+H)+; la-116 3-CFs H 3-CH3 4-(-CON(C H3)-) 環丙基 HPLC-MS:logP = 3.37 質量 (m/z) : 485.2(M+H)+; la-117 3-CFs H H 4-(-S02NH- ) 環丙基 HPLC-MS:logP = 3.33;質量 (m/z) : 493.1(M+H)+; 1HNMR (CD3CN) 0.46 — 0.56 (m,4H), 2.10-2.18 (m, 1H), 5.93 - 6.05 (m, 2H), 6.80 (d, 1H), 7.64 - 7.69 (m, 2H), 7.75 - 7.81 (m, 5H), 7.87 - 7.89 199 201136518
No. (R')n R3 (R6)m A Y HPLC- MSa); *H NMR (δ * ppm) b) (m, 3H). Ia-118 3-CF3 H 3-C1 4-(-CONH-) 環丙基 HPLC-MS:logP = 3.24;質量 (m/z) : 491.1(M+H)+; 1HNMR (CD3CN) 0.56 - 0.59 (m, 2H), 0.75 - 0.78 (m, 2H), 2.81 - 2.85 (m, 1H), 5.99 (quint, 1H), 6.71 (d, 1H), 6.94 (s, 1H), 7.46 (d, 1H), 7.52-7.67 (m, 4H), 7.76 - 7.81 (m, 3H), 7.87 (s, 1H). la-119 3-CF3 H 3-CFs 4-(-CONH-) 1,3-嘧啶-2- 基 HPLC-MS:logP = 3.11;質量 (m/z) : 563.1(M+H)+; 1HNMR (d6-DMSO) 6.17 (m, 1H), 6.98 (d, 1H), 7.20 (m, 1H), 7.60 (m, 1H), 7.70 (m, 1H), 7.82 (d, 1H), 7.93 (t, 1H), 8.01 (d, 1H), 8.61 (d, 1H), 8.42 (s, 1H), 9.55 (d, 1H), 11.3 (s, 1H). la-120 3-CFs H 3-CF3 4-(-CONH-) 6-氣。比咬-2- 基 HPLC-MS:logP = 4.33;質量 (m/z) : 594(M+H)+; 1HNMR (CD3CN) 6.01 (m, 1H), 6.82 (d, 1H), 7.18 (d, 1H), 7.65 - 7.85 (m, 6H), 7.89 (d, 1H), 7.92 (s, 1H), 8.18 (d, 1H), 9.20 (d, 1H) la-121 3-CF3 H 3-CF3 4-(-CONH-) 4-氣°比咬-2· 基 HPLC-MS : logP = 4.3;質量(m/z): 594(M+H)+; lHNMR(d6-DMSO) 6.17 (m, 1H), 6.97 (d, 1H), 7.18 (d, 1H), 7.67 - 7.85 (m, 6H), 7.93 (m, 1H), 8.04 (ss 1H), 8.18 (d, 1H), 8.42 (s, 1H), 9.60 (d, 1H), 11.3 (s, 1H). la-122 3-CF3 H 3-CF3 4-(-CONH-) 5-氯°比°定-2· 基 HPLC-MS : logP = 4.3;質量(m/z): 594(M+H)+; 1H NMR (d6-DMSO) 6.18 (m, 1H), 6.99 (d, 1H), 7.18 (d, 1H), 7.68 - 7.86 (m, 6H), 7.96 (m, 1H), 8.06 (s, 1H), 8.19 (d, 1H), 8.41 200 201136518
No. (R1)- R3 (R6)m A Y HPLC- MS a); *H NMR (δ « ppm) b) (s, 1H), 9.59 (d, 1H), 11.4 (s, 1H). Ia-123 3-CF3 H 3-CF3 5-環丙基-(1,2,4-。号二 唑)-3-基 參見合成實例9,步驟2 la-124 3-CF3 H 3-CFs 4-(-CONH-) 1-甲基°比°坐 -3-基 HPLC-MS : logP = 3.28;質量 (m/z) : 565.1(M+H)+; 1HNMR (d6-DMSO) 3.76 (s, 3H), 6.17 (m, 1H), 6.53 (s, 1H), 7.00 (d, 1H), 7.60 (s, 1H),, 7.62 - 7.69 (m, 3H), 7.81 (m, 2H), 7.95 (d, 1H), 8.04 (d, 1H), 8.18 (s, 1H), 9.58 (d, 1H), 11.00 (s, 1H). la-125 3-CF3 H 3-CFj 4-(-CONH-) 1,3-°¾咬-4-基 HPLC-MS:logP = 3.35;質量 (m/z) : 563.2(M+H)+; 1HNMR (d6-DMSO) 6.18 (m, 1H), 6.99 (d, 1H), 7.54-7.80 (m, 5H), 7.93 (m, lH),8.06(m, lH),8.19(m, 1H), 8.74 (d, 1H), 8.93 (s, 1H), 9.58 (d, 1H), 11.6 (s, 1H). la-126 3-CF3 H 3-CFs 4-(-CONH-) (4-氣"比啶 -2-基)甲基 HPLC-MS : logP = 3.68;質量 (m/z) : 610.1(M+H)+; 1HNMR (d6-DMSO) 4,55 (s, 2H), 6.17 (m, 1H), 6.98 (d, 1H), 7.49 (s, 1H), 7.65 - 7.74 (m, 3H), 7.82 (m, 2H), 8.01 (s, 1H), 8.12 (m, 1H), 8.52 (s, 1H), 9.20 (m, 1H), 9.58 (m, 1H). la-127 3-CF3 H 3-CF3 4-(-CONH-) (l,3-°f 咬-2-基)曱基 HPLC-MS : logP = 3.05;質量 (m/z) : 577.1(M+H)+; 1HNMR (d6-DMSO) 4.63 (s, 2H), 6.19 (m, 1H), 6.98 (d, 1H), 7.43 (s, 1H), 7.69 (d,2H), 7.72 (m, 2H), 7.82 (m, 2H), 7.98 (m, 1H), 8.04 (s, 1H), 8.07 (s, 1H), 8.82 (s, 1H), 9.15 (m, 1H), 9.60 (m, 1H). 201 201136518
No. (R1)- R3 (R6)m A Y HPLC- MSa); *H NMR (δ » ppm) b) Ia-128 3-CF3 H 3-CF3 4-(-CONH-) 1-(° 比咬-2-基)-乙基 HPLC-MS : logP = 3.22; f f (m/z) : 590.2(M+H)+; 1HNMR (d6-DMSO) 1.47 (d, 3H), 5.14 (s, 2H), 6.17 (m, 1H), 6.97 (d, 1H), 7.28 (m5lH)5 7.43 (d,2H), 7.65 (m, 2H), 7.72 (m, 1H), 7.80 (m, 2H), 7.96 (m, 1H), 8.05 (d, 1H), 8.53 (d, 1H), 9.01 (m, 1H), 9.55 (m, 1H). la-129 3-CF3 H 3-CF3 4-(-CONH-) 氰基甲基 HPLC-MS :logP = 3.19;質量 (m/z) : 524.1(M+H)+; 1HNMR (d6-DMSO) 4.33 (d, 2H), 6.17 (m, 1H), 7.00 (d, 1H), 7.63 (m, 1H), 7.73 (d,lH), 7.83 (m, 1H),7.72 (m,lH), 7.96 (m, 1H), 8.05 (s, 1H), 8.53 (d, 1H), 9.30(m, 1H), 9.56 (m, 1H). la-130 3-CF3 H 3-CF3 4-(-CONH-) 硫雜環丁 -3-基 HPLC-MS : logP = 3.62;質量 (m/z) : 557.1(M+H)+; 1HNMR (d6-DMSO) 3.17 (m,2H), 3.44 (m, 2H), 5.14 (m, 1H), 6.18 (m, 1H), 7.61 (d, 1H), 7.68 (d, 1H), 7.72 (m, 1H), 7.72 (m, 1H), 7.83 (m, 1H), 7.95 (m, 1H), 8.05 (d, 1H), 9.2l(m, 1H), 9.56 (m, 1H), 9.59 (m, 1H), la-131 3-CF3 H 3-CF3 4-(-CONH NMe-) 甲基 HPLC-MS :logP = 3.05;質量 (m/z) : 528.1(M+H)+; 1HNMR (d6-DMSO) 2.55 (s, 6H), 6.18 (m, 1H), 6.96 (m, 1H), 7.54 (m, 1H), 7.63 - 7.73 (m, 2H), 7.90 - 8.00 (m, 2H), 8.05 (s, 1H), 9.15(s, 1H), 9.40 (s, 1H), 9.55 (m, 1H). la-132 3-CF3 H 3-CFj 4-(-CONH-) 1-(甲氧基-羰基)乙基 HPLC-MS :logP = 3.47;質量 (m/z) : 571.1(M+H)+; 1HNMR (d6-DMSO) 1.35 (s,3H),3.67 (s, 202 201136518
No. (R!)n R3 (R6)m A Y HPLC- MS a); !H NMR (δ « ppm) b) 3H), 3.44 (m, 2H), 4.47 (m, 1H), 6.17 (m, 1H), 6.97 (d, 1H), 7.59 (d, 1H), 7.65 (s, 1H), 7.72 (m, 2H), 7.96 (m, 2H), 8.02 (s, 1H), 8.05 (s, 1H), 8.99(d, 1H), 9.56 (d, 1H). Ia-133 3-CF3 H 3-Br 4-(-CONH-) (1,3-嘧啶-2-基)曱基 HPLC-MS : logP = 2.93;質量 (m/z) : 589(M+H)+; 1HNMR (d6-DMSO) 4.64 (dd, 2H), 6.16 (m, 1H), 6.92 (d, 1H), 7.42 (m, 2H), 7.51 (m,2H) 7.67 (m,2H), 7.87 (m, 2H), 8.80(m, 1H), 9.01, (m, 1H), 9.56 (d, 1H). la-134 3-CFs H 3-Br 4-(-CONH-) 1-(〇比咬-2-基)·乙基 HPLC-MS : logP = 3.11;質量 (m/z) : 600.1(M+H)+; 1HNMR (d6-DMSO) 1.47 (d,3H),5.13 (m, 1H), 6.16 (m, 1H), 6.92 (d, 1H), 7.42 (m, 2H), 7.51 (m, 2H) 7.67 (m, 2H), 7.87 (m, 2H), 8.06 (s, 1H), 8.53 (m, 1H), 8.80(m, 1H), 9.01, (m, 1H), 9.56 (d, 1H). la-135 3-CF3 H 3-CF3 4-(111-吡唑-1-基) HPLC-MS : logP = 3.95;質量 (m/z) : 508.1(M+H)+; 1HNMR (d6-DMSO) 6.18 (m, 1H), 6.56 (m, 1H), 6.98 (d, 1H), 7.65 - 7.85 (m, 4H), 7.95 (d, 1H), 8.07 (m, 2H), 8.16 (s, lH),8.80(m, 1H), 9.58 (d, 1H). la-136 3-CF3 H 3-CFs 4-(-CONH-) 2-酮基四氫 -σ夫。南_3_基 HPLC-MS : logP = ;質量(m/z): (M+H)+; lHNMR(d6-DMSO) 2.28 (m, 2H), 4.26 (m, 2H), 4.40 (m, 2H), 4.75 (m, 1H), 6.18 (m, 1H), 6.98 (d, 1H), 7.55 -7.85 (m,4H), 7.70 (m, 1H), 8.04 (m, 2H), 9.06(m, 1H), 9.58 (d, 1H). 203 201136518
No. (R')n R3 (R6)m A Y HPLC- MS a); 'H NMR (δ * ppm) b) Ia-137 3-CF3 H 3-CF3 4-(-CONH-) 5-氣-1,3-嘧 咬_2_基 HPLC-MS : logP = 3.62;質量 (m/z) : 597(M+H)+; 1HNMR (d6-DMSO) 6.17 (m, 1H), 7.00 (d, 1H),7.65 - 7.75 (m, 2H), 7.95 (d, 1H), 7.81 (d, 2H), 7.95 (d, 2H), 8.05 (s, 1H), 8.74(s, 1H), 9.55 (d, 1H), 11.50(s, 1H) la-138 3-CF3 H 3-CF3 4-(-CONH-) 丁-3-炔-2- 基 HPLC-MS : logP = 3.58;質量 (m/z) : 537.1(M+H)+; 1HNMR (d6-DMSO) 1.37 (d, 3H), 3.19 (s, 1H), 4.77 (m, 1H), 6.18(m, 1H), 6.96 (d, 1H), 7.55 - 7.75 (m,4H), 7.80 (m, 1H), 7.93 (m, 1H), 8.04 (d, 2H), 9.0l(d, 1H), 9.55 (d, 1H). la-139 3-CF3 H 3-CFs 4-(-CONH-) 1-(〇比〇圭小 基)-丙烧,2-基 HPLC-MS : logP = 3.42;質量 (m/z) : 593.2(M+H)+; 1HNMR (d6-DMSO) 1.07 (d, 3H), 4.19(m, 2H), 4.35 (m, 1H), 6.19 (m, 1H), 6.96 (d, 1H), 7.55 - 7.75 (m, 6H), 7.81 (m, 1H), 7.92 (m, 1H), 8.05 (d, 2H), 9.0l(d, 1H), 9.55 (d, 1H). la-140 3-CF3 H 3-CF3 4-(-CONH-) 1-氰基環丙 院_1_基 HPLC-MS : logP = 3.37;質量 (m/z) : 550.1(M+H)+; 1HNMR (d6-DMSO) 1.23 (m, 2H), 1.57 (m, 2H), 4.19 (m, 2H), 4.35 (m, 1H), 6.19 (m,lH), 6.98 (d, 1H), 7.60-7.80 (m, 5H), 7.95 (m, 1H), 8.05 (d, 2H), 9.0l(d, 1H), 9.55 (d, 1H). la-141 3-CF3 H 3-CF3 4-(-CONH-) 1-氣基乙基 HPLC-MS : logP = 3.39;質量 (m/z) : 538.1(M+H)+; 1HNMR (d6-DMSO) 1.49 (d, 2H), 4.93 (m, 1H), 6.16 (m, 1H), 6.98 (d, 1H), 7.60 - 7.85 (m, 5H), 7.96 (m, 1H), 8.09 (s, 1H), 9.01(d, 1H), 9.35 (m, 1H), 9.55 (m, 1H). 204 201136518
No. (RJ)n R3 (R6)m A Y HPLC- MS a); *H NMR (δ * ppm) b) Ia-142 3-CF3 H 3-CF3 4-(-CONH-) H HPLC-MS : logP = 2.89;質量 (m/z) : 485.1(M+H)+; 1HNMR (d6-DMSO) 6.16 (m,lH), 6.98 (d, 1H), 7.55 - 7.75 (m, 5H), 7.82 (d, 1H), 7.80 - 8.00 (m, 2H), 8.05 (s, 1H), 9.0l(d, 1H), 9.50 (m, 1H). la-143 3-CF3 H 3-CF3 4-(-CONH-) 1,3-二氟丙 烧-2-基 HPLC-MS :logP = 3.48;質量 (m/z) : 563.1(M+H)+; 1HNMR (d6-DMSO) 4.03 (m, 1H), 4.47 (m, 2H), 4.61 (m, 2H), 6.17 (m, 1H), 6.97 (d, 1H), 7.60 - 7.75 (m, 5H), 7.82 (d, 1H), 7.95 (m, 1H), 8.05 (d, 1H), 8.92(d, 1H), 9.55 (m, 1H). la-144 3-CF3 H 3-CF3 4-(-CONH-) 丁烧-2-基 HPLC-MS : logP = 3.84;質量 (m/z) : 541.1(M+H)+; 1HNMR (d6-DMSO) 0.85 (m, 3H), 1.15 (d, 3H), 1.48 (m, 2H), 3.84 (m, 1H), 6.16 (m,lH), 6.95 (d, 1H), 7.50-7.75 (m, 5H), 7.82 (d, 1H), 7.90-8.10 (m, 2H), 8.35 (d, 1H), 9.55 (m, 1H). la-145 3-CF3 H 3-CF3 4-(-CONH-) 3-氯丙-2-烤 -1-基 HPLC-MS : logP = 3.69;質量 (m/z) : 559.1(M+H)+; 1HNMR (d6-DMSO) 3.87 (m, 1H), 5.95 (m, 1H), 1.48 (m, 2H), 3.84 (m, 1H), 6.16 (m,lH), 6.43 (m, 1H), 6.95 (d, 1H), 7.60 - 7.85 (m, 5H), 7.95 (m, 1H), 8.05 (d, 2H), 8.75 - 8.82 (m, 2H), 9.53 (d, 1H). la-146 3-CF3 H 3-CF3 4-(-CONH-) 2-曱基丁-3_ 炔-2-基 HPLC-MS : logP = 3.8; f f (m/z): 551,2(M+H)+; 1H NMR (d6-DMSO) 1.56 (s, 6H), 2.51 (s, 1H), 6.17 (m, 1H), 6.98 (d, 1H), 7.60 - 7.75 (m, 3H), 7.83 (m, 1H), 7.94 (m, 2H), 8.09 (d, 1H), 8.65 (s, 1H), 9.0l(d, 205 201136518
No. (R1)- R3 (R6)m A Y HPLC- MS a); !H NMR (δ « ppm)b) 1H), 9.55 (d, 1H). Ia-147 3-CF3 H 3-CF3 4-(-CONH-) 曱基 HPLC-MS : logP = 3.09;質量 (m/z) : 499.1(M+H)+; 1HNMR (d6-DMSO) 2.75 (s, 3H), 6.17 (m, 1H), 6.96 (d, 1H), 7.55 -7.85 (m, 4H), 7.83 (m, 1H), 7.95 (m, 1H), 8.05 (d, 1H), 8.41 (m, 1H), 9.01(d, 1H), 9.50 (d, 1H). la-148 3-CF3 H 3-CF3 4-(-CONH-) 1-(環丙基)- 丙-2-基 HPLC-MS : logP = 4.24;質量 (m/z) : 567.2(M+H)+; 1HNMR (d6-DMSO) 0.45 (m, 4H), 0.76 (m, 1H), 1.15 (d, 3H), 1.23 (m, 1H), 1.45 (m, 1H), 4.20 (m, 1H), 6.17 (m, 1H), 6.95 (d, 1H), 7.55 - 7.85 (m, 4H), 7.83 (m, 1H), 7.95 (m, 1H), 8.05 (d, 1H), 8.35 (m, 1H), 9.50 (d, 1H). la-149 3-CF3 H 3-CF3 4-(-CONH- 0-) 丙炫-2-基 HPLC-MS : logP = 3.48;質量 (m/z) : 543.1(M+H)+; 1HNMR (d6-DMSO) 1.20 (d,6H),4.14 (m, lH),6.16(m, 1H), 6.97 (d,lH), 7.60 - 7.85 (m, 5H), 7.95 (m, 1H), 8.05 (d, 1H), 9.55 (d, 1H), 11.50 (s, 1H). la-150 3-CF3 H 3-C1 4-(-CONH-) 丙烧-2-基 HPLC-MS : logP = 3.5;質量(m/z): 493.2(M+H)+; 1H NMR (d6-DMSO) 1.14 (d, 6H), 4.03 (m, 1H), 6.15 (m, 1H), 6.89 (d, 1H), 7.40 - 7.85 (m, 5H), 7.95 (m, 1H), 8.05 (d, 1H)S 8.31 (d, 1H), 9.55 (m, 1H). la-151 3-CF3 H 3-Cl 4-(-CONH-) 丙-2-快-1- 基 HPLC-MS : logP = 3.2;質量(m/z): 489.1(M+H)+; 1H NMR (d6-DMSO) 3.14 (s, 1H), 4.04 (m, 2H), 6.15 (m, 1H),7.00 (d, 1H), 7.45 - 7.85 (m, 206 201136518
No. (R\ R3 (R6)m A Y HPLC- MS a); NMR (δ,ppm) b) 5H), 7.95 (m, 1H), 8.05 (d, 1H), 8.98 (m, 1H), 9.50 (d, 1H). Ia-152 3-CF3 H 3-C1 4-(-CONH-) 硫雜環丁 -3-基 HPLC-MS:logP = 3.51;質量 (m/z) : 523.1(M+H)+; 1HNMR (d6-DMSO) 3.43 (m, 4H), 5.16 (m, 1H), 6.15(m, 1H), 6.90 (d, 1H), 7.45 - 7.85 (m, 5H), 7.95 (m, 1H), 8.05 (s, lH),9.10(d, 1H), 9.50 (d, 1H). la-153 3-CF3 H 3-C1 4-(-CONH-) 1,3 -嘧啶-2-基曱基 HPLC-MS : logP = 2.94;質量 (m/z) : 543.2(M+H)+; 1HNMR (d6-DMSO) 4.63 (m,2H), 6.15 (m, 1H), 6.90 (d, 1H), 7.45 - 7.85 (m, 5H), 7.95 (m, 1H), 8.05 (s, 1H), 8.80 (m, 1H), 8.97 (m, 1H), 9.50 (d, 1H). la-154 3-CFj H 3-C1 4-(-CONH-) 基)·乙基 HPLC-MS : logP = 3.45; ft (m/z) : 556.1(M+H)+; 1HNMR (d6-DMSO) 1.47 (d, 3H), 5.14 (m, 1H), 6.15 (m, 1H), 6.90 (d, 1H), 7.28 (m, 1H), 7.45 -7.85 (m, 6H), 7.95 (m, 1H), 8.05 (s, 1H), 8.55 (m, 1H), 8.93 (m, 1H), 9.50 (d, 1H). la-155 3-CF3 H 3-C1 4-(-CONH-) 1,3-二氟-丙 烧-2-基 HPLC-MS :logP = 3.36;質量 (m/z) : 529.1(M+H)+; 1HNMR (d6-DMSO) 4.03 (m, lH),4.47(m, 2H), 4.61 (m, 2H), 6.15 (m, 1H), 6.90 (d, 1H), 7.45 - 7.85 (m, 5H), 7.82 (d, 1H), 7.95 (m, 1H), 8.05 (d, 1H), 8.85(d, 1H), 9.49 (m, 1H). la-156 3-CF3 H 3-C1 4-(-CONH-) 2,2-二氟乙 基 HPLC-MS : logP = 3.34;質量 (m/z) : 515.1(M+H)+; 1HNMR (d6-DMSO) 3.65 (m, 2H), 6.15 (m, 1H), 6.90 (d, 1H), 7.45 - 7.85 (m, 207 201136518
No. Λ R3 (R6)m A Y HPLC- MSa); *Η NMR (δ · ppm) b) 5H)5 7.95 (m, 1H)? 8.05 (d51H), 8.85 (m,1H),9.50 (m5 1H). Ia-157 3-CF3 H 3-C1 4-(-CONH-) H HPLC-MS:logP = 2.75;質量 (m/z) : 451(M+H)+; 1HNMR (d6-DMSO) 6.15 (m,lH), 6.90 (d, 1H), 7.50 - 7.95 (m, 7H), 8.05 (d, 1H), 8.85 (m, 1H), 9.48 (m, 1H). la-158 3-CF3 H 3-C1 4-(-CONH-) 1,1,1-三氟-丙炫*-2_基 HPLC-MS : logP = 3.78;質量 (m/z) : 547.1(M+H)+; 1HNMR (d6-DMSO) 1.32 (d, 3H),4.77(m, lH),6.15(m, 1H), 6.90 (d, 1H), 7.45 - 7.85 (m, 6H), 7.95 (m, 1H), 8.05 (d, 1H), 9.07 (d, 1H), 9.55 (m, 1H). la-159 3-CF3 H 3-C1 4-(-CONH-) (1,3-噻唑-2-基)-曱基 HPLC-MS:logP = 3.13;質量 (m/z) : 548.1(M+H)+; 1HNMR (d6-DMSO) 4.73 (m,2H), 6.15 (m, 1H), 6.90 (d, 1H), 7.50 - 7.85 (m, 6H), 7.95 (m, 1H), 8.05 (d, 1H), 9.07 (d, 1H), 9.37 (m, 1H), 9.52 (m, 1H). la-160 3-CF3 H 3-C1 4-(-CONH-) 1-氰基乙基 HPLC-MS : logP = 3.23;質量 (m/z) : 504(M+H)+; 1H NMR (d6-DMSO) 1.50 (d, 3H), 4.95 (m, 2H), 6.15(m, 1H), 6.90 (d, 1H), 7.50-7.85 (m, 6H), 7.95 (m, 1H), 8.05 (d, 1H), 9.07 (d, 1H), 9.35 (m, 1H), 9.62 (m, 1H). la-161 3-CF3 H 3-C1 4-(-CONH-) 丁-3-炔-2- 基 HPLC-MS :logP = 3.43;質量 (m/z) : 503.1(M+H)+; 1HNMR (d6-DMSO) 1.37 (d,3H), 3.18 (m, 1H), 4.78 (m, 1H), 6.15 (m, 1H), 6.90 (d, 1H), 7.45 - 7.85 (m, 6H), 208 201136518
No. (R!)n R3 (R6)m A Y HPLC- MS a); 'H NMR (δ * ppm) b) 7.95 (m, 1H), 8.05 (d, 1H), 8.93 (d, 1H), 9.50 (d, 1H), 9.62 (m, 1H). Ia-162 3-CF3 H 3-C1 4-(-CONH-) 環丁基 HPLC-MS:logP = 3.59;質量 (m/z) : 505.1(M+H)+; 1HNMR (d6-DMSO) 1.65 (m, 2H), 2.00 (m, 2H), 2.25 (m, 2H), 3.18 (m, 1H), 4.35 (m, 1H), 6.15 (m, 1H), 6.90 (d, 1H), 7.45 - 7.85 (m, 6H), 7.95 (m, 1H), 8.05 (d, 1H), 8.68 (d, 1H), 9.50 (d, 1H). la-163 3-CF3 H 3-C1 4-(-CONH-) 環丙基甲基 HPLC-MS : logP = 3.54;質量 (m/z) : 505.1(M+H)+; 1HNMR (d6-DMSO), 1.02 (m, 4H), 3.17 (m, 2H), 4.35 (m, 1H), 6.15 (m, 1H), 6.90 (d, 1H), 7.45 - 7.85 (m, 6H), 7.95 (m, 1H), 8.05 (d, 1H), 8.51 (d, 1H), 9.50 (d, 1H). la-164 3-CF3 H 3-C1 4-(-CONH-) 1-曱氧基丙 烧-2-基 HPLC-MS : logP = 3.33;質量 (m/z) : 523.1(M+H)+; 1HNMR (d6-DMSO), 1.15 (d, 3H), 3.17 (m, 2H), 3.25 (s, 3H), 3.38 (m, 2H), 4.11 (m, 1H), 6.15(m, 1H), 6.90 (d, 1H), 7.40 - 7.85 (m, 6H), 7.95 (m, 1H), 8.05 (d, 1H), 8.34 (d, 1H), 9.50 (d, 1H). la-165 3-CF3 H 3-C1 4-(-CONH-) 4-氣吡啶-2-基 HPLC-MS : IogP = 4,23;質量 (m/z) : 562(M+H)+; 1HNMR (CD3CN) 6.02 (m, 1H), 6.78 (d, 1H), 7.20 (d, 1H), 7.55 - 7.90 (m, 8H), 8.25 (s, 1H),8.35 (s, 1H), 9.31 (s, 1H), 9.55 (m, 1H). la-166 3-CF3 H 3-C1 4-(-CONH-) U-二氧撐 基硫雜環丁 -3-基 參見合成實例10 209 201136518
No. (R*)n R3 (R6)m A Y HPLC- MSa); *Η NMR (δ · ppm)b) Ia-167 3-CF3 H 3-C1 4-(-CONH-) 1-氧撐基硫 雜環丁-3-基 參見合成實例10 la-168 3-CF3 H 3-C1 4-(-CONH-) 5-氣吡啶-2-基 HPLC-MS:IogP = 4.28;質量 (m/z) : 562.2(M+H)+; 1HNMR (d6-DMSO) 6.15 (m, 1H), 6.90 (d, 1H), 7.55 - 7.85 (m, 6H), 7.95 (m, 1H), 8.05 (s, 1H), 8.21 (m, 1H), 8.92 (d, 2H), 9.50 (d, 1H). la-169 3-CF3 H 3-CF3 4-(-CONH-) 。夫。南-2-基 曱基 HPLC-MS : logP = 3.63;質量 (m/z) : 565.1(M+H)+; 1HNMR (d6-DMSO) 4.44 (m, 2H), 6.15 (m, 1H), 6.30 (m, 1H), 6.41 (m, 1H), 6.90 (d, 1H), 7.55 - 7.85 (m, 6H), 7.95 (m, 1H), 8.05 (s, 1H), 8.21 (m, 1H), 9.02 (m, 2H), 9.50 (d, 1H). la-170 3-CF3 H 3-CF3 4-(-CONH- N(C02Me)- ) 甲基 HPLC-MS : logP = 3.23;質量 (m/z) : 572.2(M+H)+; 1HNMR (d6-DMSO) 3.15 (s,3H), 3.65 (s, 3H), 6.15 (m,lH), 6.30 (m,lH), 6.41 (m, 1H), 6.90 (d, 1H), 7.60 -8.10 (m, 6H), 7.95 (m, 1H), 8.05 (s, 1H), 8.21 (m, 1H), 9.02 (m, 2H), 9.55 (d, 1H). la-171 3-CFs H 3-CF3 4-(-CONH-) 1-(1-氣環丙 基)乙基 HPLC-MS : logP = 4.18;質量 (m/z) : 587.2(M+H)+; 1HNMR (d6-DMSO) 1.00 (m, 4H), 1.25 (d,3H),3.97 (m,lH),6.15 (m, 1H), 6.30 (m,1H),6.41 (m,1H), 6.90 (d, 1H), 7.50-7.85 (m, 6H), 7.95 (m, 1H), 8.05 (s, 1H), 8.68 (d, 1H), 9.50 (d, 1H). la-172 3-CF3 H 3-CF3 4-(-CONH-) 1-氣基-1-環 丙基乙基 HPLC-MS : logP = 3.74;質量 (m/z) : 578.3(M+H)+; 1HNMR (d6-DMSO) 0.62 (m, 4H), 1.44 210 201136518
No. (R^n R3 (R6)m A Y HPLC- MS a); *H NMR (δ > ppm) b) (m, 1H), 1.63 (s, 3H), 6.15 (m, 1H), 6.30 (m, 1H), 6.41 (m, 1H), 6.90 (d, 1H), 7.50 - 7.85 (m, 6H), 7.95 (m, 1H), 8.05 (s, 1H), 9.20 (s, 1H), 9.52 (d, 1H). Ia-173 3-CF3 H 3-Br 4-(-CONH-) 1-氟丙烷-2-基 HPLC-MS : logP = 3.35;質量 (m/z) : 555.1(M+H)+; 1HNMR (d6-DMSO) 1.03 (d, 3H), 4.27 (m, 1H), 4.30 (m, 1H), 4,45 (m, 1H), 6.15 (m, 1H), 6.90 (d, 1H), 7.41 (d, 1H), 7.54 (d, 1H), 7.67 (m, 1H), 7.80 (d, 1H), 7.89 (d, 1H), 8.04 (s, 1H), 8.52 (d, 1H), 9.45 (d, 1H) la-174 3-CF3 H 3-Br 4-(-CONH-) 丙烧-2-基 HPLC-MS : logP = 3.48;質量 (m/z) : 539(M+H)+; 1H NMR (d6-DMSO) 1.14 (d, 6H), 4.03 (m, 1H), 6.15 (m, 1H), 6.90 (d, 1H), 7.40 - 7.85 (m, 7H), 7.95 (m, 1H), 8.05 (s, 1H), 8.28 (d, 1H), 9.45 (d, 1H). la-175 3-CF3 H 3-Br 4-(-CONH-) 1,3-二氟丙 烧-2-基 HPLC-MS : logP = 3.35;質量 (m/z) : 575.1(M+H)+; 1HNMR (d6-DMSO) 4.02 (m, 1H), 4.52 (m, 2H), 4.65 (m, 2H), 6.15 (m, 1H), 6.90 (d, 1H), 7.40 - 7.95 (m, 7H), 8.05 (s, 1H),8.84 (d, 1H), 9.48 (d, 1H). la-176 3-CF3 H 3-Br 4-(-CONH-) 三氟i-丙烧-2_基 HPLC-MS :logP = 3.78;質量 (m/z) : 593.1(M+H)+; 1HNMR (d6-DMSO) 1.31(d,3H), 4.77 (m, 1H), 6.15 (m, 1H), 6.90 (d, 1H), 7.45 - 7.95 (m, 7H), 8.05 (s, 1H), 9.05 (d, 1H), 9.50 (d, 1H). 211 201136518
No. (R^n R3 (R6)m A Y HPLC- MS a>; 'H NMR (δ > ppm) b) Ia-177 3-CF3 H 3-Br 4-(-CONH-) 1,3-°塞。坐-2- 基曱基 HPLC-MS : logP = 3.14;質量 (m/z) : 592.1(M+H)+; 1HNMR (d6-DMSO) 4.73 (d, 2H), 6.15 (m, 1H), 6.90 (d, 1H), 7.45 - 7.95 (m, 7H), 8.05 (s, 1H), 9.35 (d, 1H), 9.50 (d, 1H). la-178 3-CF3 H 3-Br 4-(-CONH-) 丁-3-炔-2- 基 HPLC-MS : logP = 3.44;質量 (m/z) : 549(M+H)+; 1HNMR (d6-DMSO) 1.38(d,3H), 3.18 (s, 1H), 4.76 (m, 1H), 6.15 (m, 1H), 6.90 (d, 1H), 7.45 - 7.95 (m, 7H), 8.06 (s, 1H), 8.91 (d, 1H), 9.45 (d, 1H). la-179 3-CF3 H 3-Br 4-(-CONH-) 環丁基 HPLC-MS : IogP = 3.61;質量 (m/z) : 551.1(M+H)+; 1HNMR (d6-DMSO) 1.68 (m,2H), 2.00 (m, 2H), 2.23 (m, 2H), 4.35 (m, 1H), 6.15 (m, 1H), 6.90 (d, 1H), 7.45 -7.95 (m, 7H), 8.06 (s, 1H), 8.66 (d, 1H), 9.44 (d, 1H). la-180 3-CF3 H 3-Br 4-(-CONH-) 環丙基甲基 HPLC-MS : logP = 3.55;質量 (m/z) : 551.2(M+H)+; 1HNMR (d6-DMSO) 0.5 (m, 2H), 0.80 (m, 2H), 1.00 (m, 1H), 3.13 (m, 2H), 4.35 (m, 1H), 6.15 (m, 1H), 6.90 (d, 1H), 7.45 - 7.95 (m, 7H), 8.06 (s, 1H), 8.50 (d, 1H), 9.45 (d, 1H). la-181 3-CF3 H 3-Br 4-(-CONH-) 3-甲基硫雜 環丁-3-基 HPLC-MS:logP = 3.55;質量 (m/z) : 551.2(M+H)+; 1HNMR (d6-DMSO) 1.72 (s,3H), 2.94 (m, 2H), 3.76 (m, 2H), 4.35 (m, 1H), 6.15 (m, 1H), 6.90 (d, 1H), 7.50-7.95 (m, 7H), 8.06 (s, 1H), 8.71 (s, 1H), 9.44 (d, 1H). 212 201136518
No. (R\ R3 (R6)m A Y HPLC- MS a); !H NMR (δ » ppm) b) Ia-182 3-CF3 H 3-C1 4-(-CONH-) 1-氰基-2-甲 基-丙院-1- 基 HPLC-MS : logP = 3.68;質量 (m/z) : 532.1(M+H)+; 1HNMR (d6-DMSO) 1.07 (m,6H), 2.09 (m, 1H), 4.81(m, 1H), 6.15 (m, 1H), 6.90 (d, 1H), 7.50 - 7.95 (m, 7H), 8.06 (s, 1H), 9.30 (d, 1H), 9.44 (d, 1H). la-183 3-CF3 H 3-C1 4-(-CONH-) 3-氣°比咬-2- 基 HPLC-MS :logP = 3.44;質量 (m/z) : 562.1(M+H)+; 1HNMR (d6-DMSO) 6.16 (m, 1H), 6.91 (d, 1H), 7.38 (m, 1H), 7.50 - 7.95 (m, 9H), 8.06 (s, 1H), 8.42 (d, 1H), 9.50 (d, 1H). la-184 3-CF3 H 3-C1 4-(-CONH-) 1,3-嘧啶-4- 基 HPLC-MS :logP = 3.22;質量 (m/z) : 529.1(M+H)+; 1HNMR (d6-DMSO) 6.16 (m, 1H), 6.91 (d, 1H), 7.55 - 7.95 (m, 8H), 8.06 (s, 1H), 8.17 (m, 1H), 8.73 (d, 1H), 8.92 (s, 1H), 9.50 (d, 1H). la-185 3-CF3 H 3-C1 4-(-CONH-) 1,3-。塞唾-2- 基 HPLC-MS :logP = 3.51;質量 (m/z) : 534.1(M+H)+; 1HNMR (d6-DMSO) 6.16 (m, 1H), 6.91 (d, 1H), 7.32 (d, 1H), 7.55 - 7.95 (m, 8H), 8.05 (s, 1H), 8.17 (m, 1H), 9.50 (d, 1H). la-186 3-CF3 H 3-C1 4-(-CONH-) 1-曱基0比嗤 -3-基曱基 HPLC-MS : logP = 2.95;質量 (m/z) : 545.3(M+H)+; 1HNMR (d6-DMSO) 3.78 (s, 3H), 4.36 (m, 2H), 6.15 (m, 1H), 6.17 (d, 1H), 6.90 (d, 1H), 7.45 - 7.95 (m, 7H), 8.05 (s, 1H), 8.17 (m, lH),8.84(t, 1H), 9.47 (d, 1H). la-187 3-CF3 H 3-C1 4-(-CONH-) 1-(1,3-噻唑 -2-基)-乙基 HPLC-MS : logP = 3.4;質量(m/z): 562.1(M+H)+; 1HNMR (d6-DMSO) 1.58 (s, 3H), 5.38 (m, 1H), 6.15 (m, 213 201136518
No. (R*)n R3 (R6)m A Y HPLC- MS a); NMR (δ,卯m)的 1H), 6.90 (d, 1H), 7.45 - 7.95 (m, 8H), 8.05 (s, 1H), 8.17 (m, 1H), 9.27 (t, 1H), 9.50 (d, 1H). Ia-188 3-CF3 H 3-C1 4-(-CONH-) 1-曱基°比峻 -5-基 HPLC-MS : logP = 2.73;質量 (m/z) : 531.1(M+H)+; 1HNMR (d6-DMSO) 3.74 (s,3H),6.16 (m, 1H), 6.90 (d,1H),6.93 (d,1H),7.38 (d,1H),7.55 - 7.95 (m,8H),8.05 (s, 1H), 9.50 (d, 1H). la-189 3-CF3 H 3-C1 4-(-CONH-) (1-甲基0比 唑-5-基)曱 基 HPLC-MS : logP = 2.93;質量 (m/z) : 545.2(M+H)+; 1HNMR (d6-DMSO) 3.82 (s, 3H), 4.50 (m, 2H), 6.16 (m, 1H), 6.21 (d, 1H), 6.90 (d, 1H), 7.31 (d, 1H), 7.55 - 7.95 (m, 7H), 8.05 (s, 1H), 8.97 (t, 1H), 9.47 (d, 1H). la-190 3-CF3 H 3-C1 4-(-CONH- NMe-) 甲基 HPLC-MS :logP = 2.93;質量 (m/z) : 545.2(M+H)+; 1HNMR (d6-DMSO) 2.32 (s, 3H), 2.56 (s, 3H), 6.15 (m, 1H), 6.90 (d, 1H), 7.40 - 7.95 (m, 6H), 8.06 (s, 1H), 8.71 (s, 1H), 9.33 (s, 1H), 9.46 (d, 1H). la-191 3-CF3 H 3-C1 4-(-CONH-) 1-(曱氧基-羰基)乙基 HPLC-MS :logP = 3.29;質量 (m/z) : 537.1(M+H)+; 1HNMR (d6-DMSO) 1.35 (s,3H), 3.67 (s, 3H), 4.67 (m, 1H), 6.15(m, 1H), 6.90 (d51H), 7.45 - 7.95 (m, 7H), 8.06 (s, 1H), 8.90 (s, 1H), 9.50 (d, 1H). la-192 3-CF3 H 3-C1 4-(-CONH-) 丁烷-2-基 HPLC-MS :logP = 3.71;質量 (m/z) : 507.2(M+H)+; 1HNMR (d6-DMSO) 0.90 (t, 3H), 1.12 (d, 3H), 1.48 (m, 2H), 3.86 (m, 1H), 6.15 (m, 1H), 6.90 (d, 1H), 7.45- 214 201136518
No. (R*)n R3 (R6)m A Y HPLC- MS a); *H NMR (δ * ppm) b) 7.95 (m, 7H), 8.06 (s, 1H), 8.25 (d, 1H), 9.46 (d, 1H). Ia-193 3-CF3 H 3-C1 4-(-CONH-) 3-氣丙-2·稀 -1-基 HPLC-MS:logP = 3.58;質量 (m/z) : 525.2(M+H)+; 1HNMR (d6-DMSO) 3.91 (m, 2H), 6.02 (m, 1H), 6.15 (m, 1H), 6.42 (m, 1H), 6.90 (d, 1H), 7.50 - 7.95 (m, 7H), 8.06 (s, 1H), 8.73 (m, 1H), 9.46 (d, 1H). la-194 3-CFs H 3-C1 4-(-CONH- 0-) 丙烧-2-基 HPLC-MS : logP = 3.29;質量 (m/z) : 509.1(M+H)+; 1HNMR (d6-DMSO) 1.20 (d, 6H), 4.16(m, 1H), 6.15 (m, 1H), 6.88 (d, 1H), 7.50 -7.95(m, 7H), 8.06 (s, 1H), 9.50 (d, 1H). la-195 3-CF3 H 3-C1 4-(-CONH-) 1-乱基-1·曱 基乙基 HPLC-MS :logP = 3.34;質量 (m/z) : 518.1(M+H)+; 1HNMR (d6-DMSO) 1.66 (s, 6H), 6.15(m, 1H), 6.88 (d, 1H), 7.50- 7.95 (m, 7H), 8.06 (s, 1H), 9.06 (s, 1H), 9.47 (d, 1H). la-196 3-CFs H 3-C1 4-(-CONH-) 1-曱基丙-3-炔-1-基 HPLC-MS : logP = 3.64;質量 (m/z) : 517(M+H)+; 1HNMR (d6-DMSO) 1.57 (s, 6H), 3.30 (, 1H), 6.15 (m, 1H), 6.88 (d, 1H), 7.40 -7.95(m, 7H),8.06 (s, 1H), 8.54 (s, 1H), 9.06 (s, 1H), 9.47 (d, 1H). la-197 3-CFs H 3-C1 4-(-CONH-) 1,3-嘧啶-2- 基 HPLC-MS :logP = 2.95;質量 (m/z) : 529.1(M+H)+; 1HNMR (d6-DMSO) 6.16 (m, 1H), 6.88 (d, 1H), 7.20 (m, 1H), 7.55 - 7.95 (m, 7H), 8.06 (s, 1H), 8.62 (s, 1H), 9.06 (s, 1H), 9.50 (d, 1H). 215 201136518
No. (RJ)n R3 (R6)m A Υ HPLC- MSa); *H NMR (δ » ppm)b) Ia-198 3-CF3 H 3-Br 4-(4-氰基-1H-"比唑-1-基) HPLC-MS:logP = 2.95;質量 (m/z) : 529.1(M+H)+; 1HNMR (d6-DMSO) 6.17 (m, 1H), 6.93 (d, 1H), 7.20 (m, 1H), 7.55 - 7.95 (m, 6H),8.06 (s,1H),8.38 (s, 1H), 9.03 (s, 1H), 9.55 (d, 1H). la-199 3-CF3 H 3-C1 4-(-CONH-) 5-氣-1,3-嘧 咬-2-基 HPLC-MS:logP = 3.47;質量 (m/z) : 563(M+H)+; 1HNMR (d6-DMSO) 6.16 (m, 1H), 6.90 (d, 1H), 7.20 (m, 1H), 7.55 - 7.95 (m, 7H), 8.06 (s, 1H), 8.75 (s, 1H), 9.50 (d,1H). la-200 3-CF3 H 3-C1 4-(4-氰基-1H-吡唑-1-基) HPLC-MS:logP = 3.83;質量 (m/z) : 499(M+H)+; 1HNMR (d6-DMSO) 6.17 (m, 1H), 6.93 (d, 1H), 7.20 (m, 1H), 7.55 - 7.95 (m, 6H), 8.06 (s, 1H), 8.39 (s, 1H), 9.03 (s, 1H), 9.55 (d, 1H). la-201 3-CF3 H 3-CN 4-( 1 Η-吡唑-1-基) HPLC-MS : logP = 3.5;質量(m/z): 465(M+H)+; 1H NMR (d6-DMSO) 6.17 (m, 1H), 6.66 (s, 1H), 6.97 (d, 1H), 7.20 (m, 1H), 7.55 - 7.95 (m, 6H), 8.06 (s, 1H), 8.24 (s, 1H), 8.47(s, 1H), 9.03 (s, 1H), 9.55 (d, 1H). la-202 3- C1, 4- F H 3-C1 4-(4-氰基-1 Η-。比唑-1-基) HPLC-MS : logP = 3.77;質量 (m/z) : 483(M+H)+; 1HNMR (d6-DMSO) 6.07 (m, 1H), 6.90 (d, 1H), 7.20 (m, 1H), 7.50 - 7.95 (m, 6H), 8.00 (s, 1H), 8.40 (s51H), 9.06 (s, 1H), 9.45 (d, 1H). la-203 3-CF3 H 3-C1 4-(-CONH-) 5-氟°比咬-2- 基 HPLC-MS :logP = 3.84;質量 (m/z) : 546.1(M+H)+; 1HNMR (d6-DMSO) 6.17 (m, 1H), 6.92 (d, 1H), 7.18 (d, 1H), 7.60 - 7.69 (m, 216 201136518
No. (R^n R3 (R6)m A Y HPLC- MSa); 'H NMR (δ « ppm) b) 6H), 7.78 (m, 1H), 7.90 (s, 1H), 8.22 (m,1H),9.55 (d,1H),11.2 (s,1H). Ia-204 3-CF3 H 3-C1 4-(-CONH-) 5-硝基β比咬 -2-基 HPLC-MS:logP = 3.95;質量 (m/z) : 573(M+H)+; 1HNMR (d6-DMSO) 6.19 (m,1H),6.95 (d, 1H), 7.57 (d, 1H), 7.69 (s, 1H), 7.81 (m, 2H), 7.94 (m, 1H), 8.05 (s, 1H), 8.42 (d, 1H), 8.57 (d, 1H), 9.21 (s,1H),9.55 (m,1H),11.8 (s,1H). la-205 3-CF3 H 3-C1 4-(-CONH-) 5-氰基。比啶 -2-基 HPLC-MS : logP = 3_72;質量 (m/z) : 553.1(M+H)+; 1HNMR (d6-DMSO) 6.16 (m, 1H), 6.93 (d, 1H), 7.57 (d, 1H), 7.67 (s,1H), 7.81 (m, 2H), 7.94 (m, 1H), 8.05 (s, 1H), 8.32 (s, 1H), 8.83 (s, 1H), 9.21 (s, 1H), 9.55 (m, 1H), 11.6 (s, 1H). la-206 3-CF3 H 3-CN 4-(4-氣-1H-吡唑-1-基) HPLC-MS : logP = 3.75;質量 (m/z) : 483(M+H)+; 1HNMR (d6-DMSO) 6.07 (m, 1H), 6.92 (d, 1H), 7.20 (m, 1H), 7.55 - 7.95 (m, 5H), 8.00 (s, 1H), 8.39 (s, 1H), 9.06 (s, 1H), 9.45 (d, 1H). la-207 3-CF3 H 3-Br 4-(3-氣-1H-1,2,4-三唑-1-基) HPLC-MS : logP = 3.75;質量 (m/z) : 483(M+H)+; 1HNMR (d6-DMSO) 6.17 (m, 1H), 6.96 (d, 1H), 7.20 (m, 1H), 7.55 - 7.95 (m, 5H), 8.00 (s, 1H), 8.39 (s, 1H), 9.06 (s, 1H), 9.58 (d, 1H). la-208 3-CF3 H 3-CF3 4-(3-氣-1沁1,2,4-三唑-1- 基) HPLC-MS : logP = 4.02;質量 (m/z) : 543(M+H)+; 1HNMR (d6-DMSO) 6.18 (m, 1H), 7.04 (d, 1H), 7.20 (m, 1H), 7.70 - 7.95 (m, 5H), 8.05 (s, 1H), 8.25 (s, 1H), 9.02 (s, 1H), 9.56 (d, 1H). 217 201136518
No. (R*)n R3 (R6)m A Y HPLC- MS a); *H NMR (δ > ppm) b) Ia-209 3- C1, 4- F H 3-C1 4-(l-H-l,2,4-三唑-1-基) HPLC-MS:logP = 3.15;質量 (m/z) : 459(M+H)+; 1HNMR (d6-DMSO) 6.07(m,1H),6.93 (d, 1H), 7.20 (m, 1H), 7.70 - 7.95 (m, 5H), 8.00 (s, 1H), 8.29 (s, 1H), 9.00 (s, 1H), 9.43 (d, 1H). la-210 3-CF3 H 3-CF3 4-(-CONH-) 5-氟吡啶-2- 基 HPLC-MS:logP = 3.93;質量 (m/z) : 580.1(M+H)+; 1HNMR (d6-DMSO) 6.18 (m, 1H), 7.00 (d, 1H), 7.70 -7.73 (m, 1H), 7.67 (s, 1H), 7.96 (m, 1H), 8.06 (s, 1H), 8.18 (m, 1H), 8.37 (m, 1H), 9.55(d, 1H), 11.3 (s, 1H). la-211 3-CF3 H 3-CF3 4-(-CONH-) 5-氰基°比咬 -2-基 HPLC-MS:logP = 3.82;質量 (m/z) : 587.1(M+H)+; 1HNMR (d6-DMSO) 6.15 (m, 1H), 7.00 (d, 1H), 7.64 (d, 1H), 7.67 (s, 1H), 7.81 (m, 2H), 7.98 (m, 1H), 8.06 (d, 1H), 8.32 (m, 1H), 8.83 (s, 1H), 9.21 (s, 1H), 9.5 (d, 1H), 11.8 (s, 1H). la-212 3-CF3 H 3-Br 4-(-CONH-) 5-氟°比咬-2- 基 HPLC-MS:logP = 3.87;質量 (m/z) : 590(M+H)+; 1HNMR (d6-DMSO) 6.16 (m, 1H), 6.92 (d, 1H), 7.56 (s, 1H), 7.59 (m, 1H), 7.71 (m, 1H), 7.81 (m, 1H), 7.94 (m,2H), 8.05 (s, 1H), 8.22 (m, 1H), 8.37 (m, 1H), 9.50(d, 1H), 11.1 (s, 1H). la-213 3-CFs H 3-Br 4-(-CONH-) 5-氣°比咬-2- 基 HPLC-MS : logP = 4.25;質量 (m/z) : 591.9(M+H)+; 1HNMR (d6-DMSO) 6.16 (m, 1H), 6.92 (d, 1H), 7.55 (s, 1H), 7.59 (m, 1H), 7.71 (m, 1H), 7.82 (m, 1H), 7.96 (m, 2H), 8.05 (s, 1H), 8.21 (d, 1H), 8.41 (m, 1H), 9.52(d, 1H), 11.3 (s, 218 201136518
No. (R\ R3 (R6)m A Y HPLC- MS a); *H NMR (δ * ppm) b) 1H). Ia-214 3-CF3 H 3-Br 4-(-CONH-) 5-氰基。比啶 -2-基 HPLC-MS:logP = 3.75;質量 (m/z) : 599(M+H)+; 1HNMR (d6-DMSO) 6.16 (m, 1H), 6.90 (d, 1H), 7.47 (d, 1H), 7.62 (m,1H), 7.72 (m,2H),7.81 (m,1H),8.05 (s, 1H), 8.32 (m, 1H), 8.83 (s, 1H), 9.21 (s, 1H), 9.53 (d, 1H), 11.6 (s, 1H). la-215 3-CF3 H 3-C1 4-(-CONH-) 5-石肖基°比咬 •2-基 HPLC-MS : logP = 3.97;質量 (m/z) : 619(M+H)+; 1HNMR (d6-DMSO) 6.17 (m, 1H), 6.93 (d, 1H), 7.56 (d, 1H), 7.66 (d, 1H), 7.71 (m, 2H), 7.81 (m, 1H), 7.96 (s, 1H), 8.69 (d, 1H), 8.55 (d, 1H), 9.21 (s, 1H), 9.52 (m, 1H), 11.9 (s, 1H). la-216 3-CF3 H 3-C1 4-(-CONH-) 1,4_0比口井_2- 基 HPLC-MS:logP = 3.31;質量 (m/z) : 529.1(M+H)+; 1HNMR (d6-DMSO) 6.16 (m, 1H), 6.91 (d, 1H), 7.50 -7.95 (m, 7H), 7.96 (s, 1H), 8.45 (m, 1H), 8.55 (d, 1H), 9.41 (s, 1H), 9.52 (m, 1H) la-217 3-CF3 H 3-C1 4-(-CONH-) 1,2-嗒畊-3- 基 HPLC-MS:logP = 3.29;質量 (m/z) : 529(M+H)+; 1HNMR (d6-DMSO) 6.15 (m, 1H), 6.92 (d, 1H), 7.50 -7.95 (m, 7H), 7.96 (s, 1H), 8.46 (m, 1H), 8.55 (d, 1H), 9.40 (s, 1H), 9.52 (m, 1H) la-218 3-CFs H 3-C1 4-(-CONH-) 5-(曱氧基-羰基)吡啶 -2-基 HPLC-MS : logP = 3.92;質量 (m/z) : 586.1(M+H)+; 1HNMR (d6-DMSO) 3.88 (s, 3H), 6.16 (m, 1H), 6.93 (d, 1H), 7.56 (s, 1H), 7.59 (m, 1H), 7.67 (s, 1H), 7.81 (s, 1H), 7.95 (m, 2H), 8.05 (s, 1H), 219 201136518
No. (R^n R3 (R6)m A Y HPLC- MS a); lH NMR (δ > ppm)b) 8.22 (m,1H),8.36 (m,1H),8.89 (s, 1H), 9.52 (d, 1H), 11.5 (s, 1H). Ia-225 3-CF3 H 3-CF3 4-(-CONH-) 1,2-嗒畊-3- 基 HPLC-MS:logP = 3.27;質量 (m/z) : 563(M+H)+; 1HNMR (d6-DMSO) 6.18 (m,1H),7.00 (d, 1H), 7.65 -8.00 (m, 8H), 8.10 (d, 1H),8.36 (d,1H),9.05 (m,1H),9.55 (d, 1H). la-226 3-CF3 H 3-CF3 4-(-CONH-) 5-溴-1,4·。比 畊 HPLC-MS:logP = 4.15;質量 (m/z) : 643(M+H)+; 1H NMR (d6-DMSO) 6.18 (m, 1H), 7.00 (d, 1H), 7.65 -8.00 (m, 7H), 8.10(d, 1H), 8.67 (s, 1H), 9.20 (s, 1H), 9.55 (d, 1H). la-227 3-CF3 H 3-CF3 4-(-CONH-) 1-氧撐基硫 雜環丁-3-基 HPLC-MS : logP = 2.71;質量 (m/z) : 573.1(M+H)+; 1HNMR (d6-DMSO) 3.15 (m, 2H), 4.10 (m, 2H), 4.35 (m, 1H), 6.17 (m, 1H), 6.95 (d, 1H), 7.65 - 8.00 (m, 7H), 8.05 (d, 1H), 9.16 (d, 1H), 9.50 (d, 1H). la-228 3-CF3 H 3-C1 4-(-CONH-) 6-氣-1,2-π 比 。井-3-基 HPLC-MS : logP = 3.7;質量(m/z): 563(M+H)+; 1H NMR (d6-DMSO) 6.17 (m, 1H), 6.94 (d, 1H), 7.55 -7.95 (m, 8H), 8.06 (d, 1H), 8.48 (d, 1H), 9.05 (m, 1H), 9.55 (d, 1H). la-229 3-CF3, 5-F H 3-CF3 4-(-CONH-) 環丙基 參見合成實例17,步驟4 la-230 3-F H 3-CF3 4-(-CONH-) 環丙基 HPLC-MS :logP = 2.95;質量 (m/z) : 475.1(M+H)+; lHNMR(d3-乙腈)0.55 (m,2H),0.75 (m,2H), 2.80 (m, 1H), 5.90 (m, 1H), 6.80 (d, 1H), 6.90 (br. s, 1H), 7.17-7,52 (m. 5H), 7.64 (d, 1H), 7.71-7.83 (m, 2H), 220 201136518
No. (R1)- R3 (R6)™ A Y HPLC- MS a); !H NMR (δ > ppm) b) 7.90 (s, 1H). Ia-231 3-C1 H 3-CF3 4-(-CONH-) 環丙基 HPLC-MS : logP = 3.22;質量 (m/z) : 491.1(M+H)+; 1HNMR (d6-DMSO) 0.50 (m, 2H), 0.69 (m, 2H), 2.80 (m, 1H), 6.01 (m, 1H), 6.95 (d, 1H), 7.47-7.64 (m, 4H), 7.70 (d, 1H), 7.73 (s, 1H), 7.91 (m51H), 7.98 (m, 1H), 8.53 (m, 1H), 9.40 (m, 1H). la-232 3-CH3 H 3-CF3 4-(-CONH-) 環丙基 HPLC-MS : logP = 3.17;質量 (m/z) : 471.1(M+H)+; 1HNMR (d6-DMSO) 0.50 (m, 2H), 0.69 (m, 2H), 2.34 (s, 3H), 2.79 (m, 1H), 5.85 (m, 1H), 6.97 (d, 1H), 7.23 (m, 1H), 7.31-7.40 (m, 3H), 7.54 (m, 1H), 7.62 (d, 1H), 7.89 (m, 1H), 7.97 (s, 1H), 8.53 (m, 1H), 9.32 (m, 1H). la-233 3-CFs H 2-C1 4-(-CONH-) 環丙基 HPLC-MS : logP = 3.46;質量 (m/z) : 491.2(M+H)+; lHNMR(d3-乙腈)0.61 (m,2H),0.75 (m,2H), 2.83 (m, 1H), 6.01 (m, 1H), 6.76 (d, 1H), 7.14 (br. s, 1H), 7.65-7.92 (m, 8H), 7.93 (m, 1H). la-234 3-C1 H 2-C1 4-C-CONH-) 環丙基 HPLC-MS : logP = 3.3;質量(m/z): 457.1(M+H)+; lHNMR(d3-乙腈) 0.60 (m, 2H), 0.75 (m, 2H), 2.84 (m, 1H), 5.90 (m, 1H), 6.75 (d, 1H), 7.14 (br. s, 1H), 7.44-7.48 (m, 3H), 7.57 (s, 1H), 7.14-7.84 (m, 4H), 7.93 (d, 1H). la-235 3-Cl H 3-C1 4-(-CONH-) 環丙基 HPLC-MS : logP = 3.03;質量 (m/z) : 457(M+H)+; 1HNMR (d6-DMSO) 0.53 (m, 2H), 0.69 (m, 221 201136518
No. (R*)n R3 (R6)m A Y HPLC- MS a); *H NMR (δ » ppm) b) 2H), 2.82 (m, 1H), 6.01 (m, 1H), 6.88 (d, 1H), 7.43-7.61 (m, 6H), 7.73 (m, 2H),8.49 (d, 1H), 9.38 (d, 1H). Ia-236 3-CF3 H 3-C1 4-(-CONH-) (5-氟吡啶 -2-基)曱基 HPLC-MS:logP = 3.15;質量 (m/z) : 560.22(M+H)+; 1HNMR (400 MHz, d3-CD3CN) : 8.38 (m, 1H), 7.87 (s, 1H), 7.85-7.75 (m, 4H), 7.68-7.64 (m, 2H), 7.60-7.50 (m, 4H), 7.40-7.30 (m, 1H), 6.74 (d, 1H, J=16Hz), 6.00 (m, 1H), 4.72 (dd, 1H). la-237 3-CF3 H 3-Br 4-(-CONH-) 1-乙氧基環 丙烧-1_基 HPLC-MS : logP = 3.42;質量 (m/z) : 579.34(M+H)+; la-238 3-CF3 H 3-CF3 4-(-CH2NH CO-) 乙基 HPLC-MS : logP = 3.51;質量 (m/z) : 527.1(M+H)+; 1HNMR (d3-CD3CN) 7.86 (m, 2H), 7.80-7.70 (m, 4H), 7.68-7.63 (m, 2H), 7.55 (d, 1H), 6.80 (s, 1H, br), 6.74 (d, 1H, J=16Hz), 5.99 (m, 1H), 4.51 (d, 2H), 2.24 (q, 2H), 1.10 (t, 3H) la-239 3-CF3 H 3-CF3 4-(-CON(C h3)-) °比咬-2-基 HPLC-MS :logP = 2.07;質量 (m/z) : 576.22(M+H)+; 1HNMR (400 MHz, d3-CD3CN) : 8.30 (d, 1H), 8.00 (d, 1H), 7.90 (m, 2H), 7.80-7.60 (m, 9H), 6.80 (m, 1H), 6.00 (m, 1H), 3.78 (m, 3H) la-240 3-CF3 H 3-CF3 4-(-CH2NH CO-) 環丙基 HPLC-MS : logP = 3.76;質量 (m/z) : 539.15(M+H)+; 1HNMR (400 MHz, d3-CD3CN) : 7.90-7.75 (m, 5H), 7.70-7.60 (m, 3H), 7.55 (d, 1H), 7.09 (t, 1H, br), 6.75 (d, 1H, J=16Hz), 6.02 (m, 1H), 4.54 (d, 2H), 222 201136518
No. (R、 R3 (R6)m A Y HPLC- MS a); NMR (δ > ppm) b) 1.55 (m, 1H), 0.80 (m, 2H), 0.75 (m, 2H) Ia-241 3-cf3 H H 4-(-CH2NH CO-) 乙基 HPLC-MS : logP = 2.8;質量(m/z): 459.17(M+H)+; 1H NMR (400 MHz, d3-CD3CN): 7.88 (s, 1H), 7.85-7.75 (m, 3H), 7.70-7.60 (m, 2H), 7.55 (d, 2H), 7.30 (d, 2H), 6.80 (s, 1H, br), 6.68 (d, 1H, J=16Hz), 6.00 (m, 1H), 4.38 (d, 2H), 3.30 (q, 2H), 1.10 (t, 3H) la-242 3-CF3 H 3-CF3 4-(-CONH-) 環丙基 HPLC-MS : logP = 2.07;質量 (m/z) : 519.45(M+H)+; 1HNMR (400 MHz, d6-DMSO) : 9.60 (dd, 1H), 8.53 (m, 1H), 8.00-7.95 (m, 2H), 7.90 (d, 1H), 7.78 (m, 1H), 7.73 (m, 1H), 7.68-7.63 (m, 2H), 7.53 (m, 1H), 6.97 (m, 1H), 6.08 (m, 1H), 2.78 (m, 3H), 0.70 (m, 2H), 0.50 (m, 2H) la-243 3-s〇2c h3 H 3-CF3 4-(-CONH-) 環丙基 HPLC-MS :logP = 2.31;質量 (m/z) : 535.47(M+H)+; la-244 3-so2c h3 H 3-CF3 4-C-CONH-) °比咬-2·基 HPLC-MS : logP = 2.62;質量 (m/z) : 572.48(M+H)+; 1HNMR (400 MHz, d6-DMSO) : 11.16 (s, 1H), 9.61 (d, 1H), 8.36 (s, 1H, br), 8.24 (s, 1H), 8.15 (m, 1H), 8.06 (s, 1H), 8.03-7.96 (m, 3H), 7.82 (m, 1H), 7.76-7.71 (m, 2H), 7.70 (d, 1H, J=16Hz), 7.18 (dd, 1H), 7.00 (d, 1H, J=16Hz), 6.20 (m, 1H), 3.27 (s, 3H) la-245 3-SOCH 3 H 3-CF3 4-(-CH2NH CO-) 甲基 HPLC-MS : logP= 1.98;質量 (m/z) : 507.49(M+H)+; 223 201136518
No. (R*)n R3 (R6)m A Y HPLC- MS a); *H NMR (δ « ppm) b) Ia-246 3-C1 H 3-CF3 4-(-CONH-) °比咬-2-基 HPLC-MS:logP = 3.37;質量 (m/z) : 528.38(M+H)+; 1HNMR (400 MHz, d3-CD3CN) : 8.60 (d, 1H), 8.32 (d, 1H), 8.21 (d, 1H), 7.98 (s, 1H), 7.92 (d, 1H), 7.83 (m, 1H), 7.72 (d, 1H), 7.68 (d, 1H, J=16Hz), 7.61 (s, 1H), 7.51-7.45 (m, 4H), 7.16 (dd, 1H), 6.90 (d, 1H, J=16Hz), 5.90 (m, 1H) la-247 3-CF3 H 3-CF3 4-(-CH2NH CO-) 甲基 HPLC-MS:logP = 3.24;質量 (m/z) : 513.1(M+H)+; 1H NMR (400 MHz, d3-CD3CN) : 7.87 (m, 2H), 7.82-7.76 (m, 4H), 7.67-7.62 (m, 2H), 7.55 (d, 1H), 6.87 (s, 1H, br), 6.75 (d, 1H, J=16Hz), 6.00 (m, 1H), 4.51 (d, 2H), 2.50 (s, 3H) la-248 3-CF3 H 3-C1 4-(-CH2NH CO·) 甲基 HPLC-MS:logP = 3.06;質量 (m/z) : 479.1(M+H)+; 1H NMR (400 MHz, d3-CD3CN) : 7.82 (s, 1H), 7.80-7.75 (m, 3H), 7.65 (dd, 1H), 7.60 (s, 1H), 7.55 (d, 1H, J=16Hz), 7.50 (d, 1H), 7.38 (d, 1H), 6.85 (s, 1H, br), 6.69 (d, 1H, J=16Hz), 6.00 (m, 1H), 4.40 (d, 2H), 2.50 (s, 3H) la-249 3-CF3 H 3-CH3 4-(-CH2NH CO-) 曱基 HPLC-MS : logP = 2.9;質量(m/z): 459.1(M+H)+; 1H NMR (400 MHz, d3-CD3CN) : 7.86 (s, 1H), 7.80 (d, 1H), 7.77 (d, 1H), 7.72 (d, 1H), 7.66 (dd, 1H), 7.56 (d, 1H, J=16Hz), 7.39 (m, 2H), 7.25 (d, 1H), 6.71 (s, 1H, br)5 6.64 (d, 1H, J=16Hz), 5.99 (m, 1H), 4.31 (d,2H), 2.31 (s, 3H) la-250 3-CF3 H 3-F 4-(-CH2NH- ) σ比咬-2-基 曱基 HPLC-MS : logP = ;質量(m/z): 512.5(M+H)+; 1H NMR (400 MHz, d3-CD3CN) : 8.50 (d, 1H), 7.87 (s, 224 201136518
No. (R')n R3 (R6)m A Y HPLC- MS a); *H NMR (δ « ppm) b) 1H), 7.80-7.65 (m, 5H), 7.58 (d, 1H, J=16Hz), 7.50 (dd, 1H), 7.38 (m, 1H), 7.30 (d, 1H), 7.20 (dd, 1H), 6.67 (d, 1H, J=16Hz), 6.00 (m, 1H), 3.86 (m, 4H), 2.40-2.20 (s, 1H, br) Ia-251 3- C1, 4- F H 3-CF3 4-(-CH2NH CO-) 乙基 HPLC-MS : IogP = 3.47;質量 (m/z) :511.1 (M+H)+; 1H NMR (d6-DMSO) 9.39 (d, 1H), 8.36 (t, 1H), 7.90-7.85 (m, 2H), 7.70-7.60 (m, 2H), 7.53-7.49 (m, 2H), 6.88 (d, 1H, J=16 Hz), 6.05 (m, 1H), 4.44 (d, 2H), 2.20 (q, 2H), 1.05 (t, 3H) la-252 3-CF3 H 3-F 4-(-CH2N(C 〇CH3)-) 11比咬-2-基 曱基 HPLC-MS : logP = 2.72;質量 (m/z) : 554.49(M+H)+; 1HNMR (400 MHz, d3-CD3CN) : 8.53 (d, 1H),8.44 (d,1H,旋轉異構物),7.87 (s, 1H), 7.80-7.65 (m, 5H), 7.55 (m, 1H), 7.40-7.20 (m, 5H), 6.70-6.65 (m, 1H), 5.99 (m, 1H), 4.69 (s, 2H, 旋轉異構物),4.61-4.57 (m, 4H), 1.09 (s, 3H, isomer), 1.08 (s, 3H) la-253 3-CF3 H 3-F 4-(-CH2N(C OiPr)-) 0比咬-2-基 曱基 HPLC-MS :logP = 3.37;質量 (m/z) : 582.48(M+H)+; 1HNMR (400 MHz, d3-CD3CN) : 8.53 (m, lH),8.48(m,lH,旋轉異構物), 7.85 (s, 1H), 7.70-7.50 (m, 7H), 7.30-7.20 (m, 4H), 6.65 (m, 1H), 6.00 (m,1H), 4.71 (s,2H,旋轉異構 物),4.65-4.60 (m,4H),2.90 (m,1H), 1.05 (m, 6H) la-254 3-CF3 H H 4-(-CH2N(C 〇CH3)-) 。比咬-2·基 曱基 HPLC-MS : logP = 2.65;質量 (m/z) : 536.43(M+H)+; 1HNMR (400 MHz, d3-CD3CN) : 8.53 (m, lH),8.47(m,lH,旋轉異構物), 7.87 (s, 1H), 7.70-7.50 (m, 9H), 225 201136518
No. (R')n R3 (R6)m A Y HPLC- MS a); 'H NMR (δ > ppm) b) 7.30-7.20 (m, 3H), 6.70-6.65 (m, 1H),6.00 (m,1H),4.66 (s,2H,旋轉 異構物),4.57-4.59 (m,4H),1.08 (m, 3H) Ia-255 3-CF3 H 3-CF3 4-(-CONH-) 3-曱基吡啶 -2-基 HPLC-MS:logP = 3.19;質量 (m/z) : 576.4(M+H)+; 1H NMR (400 MHz,d3-CD3CN) · 8.80 (s,1H, br), 8.22 (s,1H),8.00 (s,1H),7.90-7.85 (m,3H), 7.80 (d,1H),7.75 (d,1H), 7.70-7.65 (m, 4H), 7.20 (m, 1H), 6.83 (d, 1H, J=16Hz), 6.00 (m, 1H), 2.32 (s,3H) la-256 3-SCF3 H 3-CF3 4-(-CONH-) 環丙基 HPLC-MS:IogP = 3.51;質量 (m/z) : 557.3(M+H)+; 1H NMR (400 MHz, d3-CD3CN) : 7.90 (m,3H), 7.80-7.75 (m, 2H), 7.72 (d, 1H), 7.63 (d, 1H, J=16Hz), 7.60 (m, 1H), 7.45 (d, 1H), 6.97 (s, 1H), 6.79 (d, 1H, J=16Hz), 5.97 (m, 1H), 2.89 (m, 1H), 0.75 (m, 2H), 0.55 (m, 2H) la-257 3-CF3 H 3-CF3 4-(-CON(Et )-) 環丙基 HPLC-MS:logP = 3.89;質量 (m/z) : 553.4(M+H)+; 1H NMR (400 MHz, d3-CD3CN) : 8.00 (d, 1H), 7.90 (s, 1H), 7.88 (s, 1H), 7.85-7.75 (m, 3H), 7.68 (m, 2H), 7.55 (d, 1H), 6.82 (d, 1H, J=16Hz), 6.00 (m, 1H), 3.52 (q, 2H), 1.50 (m, 1H), 1.20 (t, 3H), 0.93 (m, 1H), 0.55 (m, 4H) la-258 3-CF3 H 3-CF3 4-(-CON(cP r)-) 0比咬-3-基 甲基 HPLC-MS : logP = 2.8;質量(m/z): 616.4(M+H)+; 1H NMR (400 MHz, d3-CD3CN) : 8.61 (s, 1H), 8.52 (m, 1H), 8.20 (d, 1H), 7.93 (s, 1H), 7.89 (s, 1H), 7.85-7.80 (m, 2H), 7.75 (m, 2H), 7.65 (m, 2H), 7.50 (d, 1H), 7.35 (dd, 1H), 6.84 (d, 1H, J=16Hz), 6.00 226 201136518
No. (R\ R3 (R6)m A Y HPLC- MS a); NMR (δ,卯m) b) (m,1 Η), 4.75-4.70 (s,2H,br), 1.40-1.30 (m, lH),0.50(m, 4H) Ia-259 3-CF3 H 3-CF3 4-(-CONH-) 4-曱基吡啶 -2-基 HPLC-MS:logP = 3.61;質量 (m/z) : 576.4(M+H)+; 1HNMR(400 MHz, d3-CD3CN) : 9.40 (s, 1H, br), 8.09 (s, 1H), 8.05 (s, 1H), 7.95 (d5 1H), 7.90 (s5 1H), 7.86 (m, 2H), 7.80 (d, 1H), 7.75 (d, 1H), 7.65 (m, 2H), 7.59 (d, 1H), 6.96 (m, 1H), 6.81 (d, 1H, J=16Hz), 6.08 (m, 1H), 2.39 (s, 3H) la-260 3-CF3 H 3-CFs 4-(-CONH-) 4-氰基°比啶 -2-基 HPLC-MS : logP = 3.61;質量 (m/z) : 587.4(M+H)+; 1HNMR(400 MHz, d3-CD3CN) : 9.43 (s, 1H, br), 8.50 (m, 2H), 8.00 (s, 1H), 7.93 (d, 1H), 7.88 (m, 2H), 7.80 (d, 1H), 7.75 (d, 1H), 7.73-7.65 (m, 3H), 7.45 (dd, 1H), 6.85 (d, 1H, J=16Hz), 6.02 (m, 1H) la-261 3-CF3 H 3-CF3 4-(-CONH-) 反式-2-甲 基-環丙基 HPLC-MS : logP = 3.46;質量 (m/z) : 539.4(M+H)+; 1HNMR(400 MHz, d3-CD3CN) : 7.90-7.78 (m, 6H), 7.65 (m, 3H), 7.50 (d, 1H), 6.90 (s, 1H), 6.78 (d, 1H, J=16Hz), 6.00 (m, 1H), 2.45 (m, 1H), 1.10 (d, 3H), 0.93 (m, 1H), 0.70 (m, 1H), 0.55 (m, 1H) la-262 3-CF3 H 3-CF3 4-(-CONHC H2CONH-) 2,2,2-三氟 乙基 HPLC-MS :logP = 3.11;質量 (m/z) : 624.4(M+H)+; 1HNMR(400 MHz, d3-CD3CN) : 7.94 (s, 1H), 7.88 (m, 2H), 7.85-7.75 (m, 3H), 7.70-7.60 (m, 3H), 7.20 (t, 1H), 7.00 (s, 1H, br), 6.80 (d, 1H, J=16Hz), 6.00 (m, 1H), 4.01 (d, 2H), 3.95 (m, 2H) 227 201136518
No. (R1)- R3 (R6)m A Y HPLC- MS a); *H NMR (δ « ppm) b) Ia-263 3-CF3 H 3-CF3 4-(-CH2NH- ) 0比咬-2-基 HPLC-MS : logP = 2.2;質量(m/z): 548.4(M+H)+; 1H NMR (400 MHz, d3-CD3CN) : 7.97 (d, 1H), 7.88 (s, 1H), 7.86 (s, 1H), 7.70-7.60 (m, 4H), 7.65-7.60 (m, 3H), 7.40 (dd, 1H), 6.73 (d, 1H, J=16Hz), 6.56 (dd, 1H), 6.53 (d, 1H), 6.02 (m, 1H), 5.72 (m, 1H, br), 4.73 (d, 2H) la-264 3-CF3 H 3-CF3 4-(-CH2NH- ) 4-氣。比咬-2- 基 HPLC-MS : logP = 4.28;質量 (m/z) : 582.3(M+H)+; 1H NMR (400 MHz, d3-CD3CN) : 7.90-7.88 (m, 3H), 7.80-7.750 (m, 4H), 7.65-7.60 (m, 3H), 6.74 (d, 1H, J=16Hz), 6.60 (dd, 1H), 6.56 (d, 1H), 6.01 (m, 1H), 5.98 (t, 1H, br), 4.73 (d, 2H) la-265 3-CF3 H H 4-(-CH2NH- ) 4-氣吡啶-2- 基 HPLC-MS:logP = 3.15;質量 (m/z) : 514.4(M+H)+; 1H NMR (400 MHz, d3-CD3CN) : 7.92 (d, 1H), 7.85 (d, 1H), 7.80-7.70 (m, 3H), 7.65 (t, 1H), 7.60 (d, 1H), 7.53 (d, 2H), 7.36 (d, 2H), 6.66 (d, 1H, J=16Hz), 6.57 (m, 1H), 6.49 (d, 1H), 6.02 (m, 1H), 5.92 (t, 1H), 4.53 (d, 2H) la-266 3-CF3 H 3-CFa 4-(-CH2NH CO-) 異丙基 參見合成實例16,步驟6 la-267 3-CF3 H 3-CF3 4-(-CH2NH CO-) 環丁基 HPLC-MS : logP = 19;質量(m/z): 553.2(M+H)+; lHNMR(d6-DMSO 9.49 (d, 1H), 8.25 (t, 1H), 8.05 (s, 1H), 7.95 (m, 2H), 7.87 (d, 1H), 7.81 (d, 1H), 7.70 (t, 1H), 7.61 (d, 1H, J=16Hz), 7.48 (d, 1H), 6.90 (d, 1H, J=16 Hz), 6.15 (m, 1H), 4.43 (d, 2H), 3.10 (m, 1H), 2.20-2.00 (m, 4H), 1.90-1.80 (m, 2H) 228 201136518
No. (R!)n R3 (R6)m A Y HPLC- MS a); NMR (δ * ppm) b) Ia-268 3-CF3 H 3-CF3 4-(-CH2NH CO-) D塞吩-3-基 HPLC-MS:logP = 3.92;質量 (m/z) : 581.1(M+H)+; 1HNMR (d6-DMSO) 9.50 (d, 1H), 8.94 (t, 1H), 8.22 (dd, 1H), 8.05 (s, 1H), 7.95-7.87 (m, 3H), 7.81 (d, 1H), 7.70 (t, 1H), 7.62-7.58 (m, 2H), 7.55 (m, 2H), 6.90 (d, 1H, J=16 Hz), 6.15 (m, 1H), 4.63 (d, 2H) la-269 3-CF3 H 3-CF3 4-(-CH2NH CO-) 5-酮基四氫 -σ夫喃-3-基 HPLC-MS:logP = 3.34;質量 (m/z) : 583.1(M+H)+; la-270 3-CF3 H 3-CF3 4-(-CH2NH CO-) 曱基硫曱基 HPLC-MS:logP = 3.84;質量 (m/z) : 599.2(M+H)+; 1HNMR (d6-DMSO) 9.46 (d, 1H), 8.44 (t, 1H),8.05 (s, 1H), 7.95 (m, 2H), 7.85-7.80 (m, 2H), 7.70 (t, 1H), 7.62 (d, 1H, J=16Hz), 7.50 (d, 1H), 6.90 (d, 1H, J=16 Hz), 6.16 (m, 1H), 4.44 (d, 2H), 2.04 (s, 3H), 1.53 (s, 6H) la-271 3-CF3 H 3-CF3 4-(-CH2NH SO2-) 環丙基 HPLC-MS : logP = 3.74;質量 (m/z) : 575.1(M+H)+; 1HNMR (d6-DMSO) 9.50 (d, 1H), 8.05 (s, 1H), 7.95 (m, 2H), 7.85-7.80 (m, 3H), 7.70 (t, 1H),7.61 (d, 1H, J=16Hz), 6.90 (d, 1H, J=16 Hz), 6.16 (m, 1H), 4.38 (d, 2H), 2.55 (m, 1H), 0.89 (m, 4H) la-272 3- CFs, 4- F H 3-CF3 4-(-CH2NH CO-) 乙基 HPLC-MS:logP = 3.61;質量 (m/z) : 545.2(M+H)+; 1HNMR (d6-DMSO) 9.49 (d, 1H), 8.36 (t, 1H), 8.12 (m, 1H), 8.05 (m, 1H), 7.94 (s, 1H), 7.88 (d, 1H), 7.67-7.60 (m, 2H), 7.53 (d, 1H), 6.88 (d, 1H, J=16 Hz), 6.19 (m, 1H), 4.44 (d, 1H), 2.22 (q, 2H), 1.05 (t, 2H) 229 201136518
No. (R】)n R3 (R6)m A Y HPLC- MS a); *H NMR (δ » ppm) b) Ia-273 3-CF3 H 3-F 4-(-CH(CH3 )NHCO-) 乙基 HPLC-MS : logP = 3.3; f #(m/z): 491,2(M+H)+; 1H NMR (d6-DMSO) 9.47 (d, 1H), 8.28 (d, 1H), 8.05 (s, 1H), 7.95 (d, 1H), 7.80 (d, 1H), 7.70 (t, 1H), 7.52 (d, 1H, J=16Hz), 7.41-7.38 (m, 2H), 6.80 (d, 1H, J=16 Hz), 6.15 (m, 1H), 5.10 (m, 1H), 2.13 (q, 2H), 0.98 (t, 2H) la-274 3- Cl, 4- F H 3-F 4-(-CH(CH3 )NHCO-) 乙基 HPLC-MS :logP = 3.23;質量 (m/z) : 475.2(M+H)+; 1HNMR (d6-DMSO) 9.37 (d, 1H), 8.28 (d, 1H), 7.90 (m, 1H), 7.68 (m, 1H), 7.55-7.49 (m, 2H), 7.40-7.35 (m, 3H), 6.78 (d, 1H, J=16 Hz), 6.05 (m, 1H), 5.10 (m, 1H), 2.13 (q, 2H), 1.33 (d, 3H), 0.98 (t, 3H) la-275 3- CFs, 4- F H 3-F 4-(-CH(CH3 )NHCO-) 乙基 HPLC-MS :logP = 3.38;質量 (m/z) : 509.2(M+H)+; 1HNMR (d6-DMSO) 9.46 (d, lH),8.28(d, 1H), 8.13 (m, lH),8.05(m, 1H), 7.64 (t, 1H), 7.52 (d, 1H, J=16Hz), 7.41-7.37 (m, 3H), 6.77 (d, 1H, J=16 Hz), 6.19 (m, 1H), 5.10 (m, 1H), 2.13 (q, 2H), 1.33 (d, 3H), 0.98 (t, 3H) la-276 3-CF3 H 3-F 4-(-CH2NH CO-) 乙基 HPLC-MS : logP = 3.12;質量 (m/z) : 477.2(M+H)+; 1HNMR (d6-DMSO) 9.47 (d, 1H), 8.27 (t, 1H), 8.05 (s, 1H), 7.94 (d, 1H), 7.80 (d, 1H), 7.71 (t, lH),7.52(d, 1H, J=16Hz), 7.40 (m, 2H), 7.35 (t, 1H), 6.80 (d, 1H, J=16 Hz), 6.15 (m, 1H), 4.29 (d, 2H), 2.15 (q, 2H), 1.02 (t, 3H) la-277 3- C1, 4- F H 3-F 4-(-CH2NH CO-) 乙基 HPLC-MS : logP = 3.06;質量 (m/z) : 461.2(M+H)+; 1HNMR 230 201136518
No. (R、 R3 (R6)m A Y HPLC- MS a); 'H NMR (δ - ppm) b) (d6-DMSO) 9.37 (d, 1H), 8.27 (t, 1H), 7.90 (d, 1H), 7.65 (m, 1H), 7.54-7.50 (m, 2H), 7.43-7.39 (m, 2H), 7.35 (t, 1H), 6.79 (d, 1H, J-16 Hz), 6.05 (m, 1H), 4.30 (d, 2H), 2.15 (q,2H),1.02(t,3H) Ia-278 3- CF3, 4- F H 3-CF3 4-(-CH2NH CO-) 乙基 HPLC-MS:logP = 3.21;質量 (m/z) : 495.1(M+H)+; 1HNMR (d6-DMSO) 9.46 (d, 1H), 8.27 (t, 1H), 8.12 (d, 1H), 8.02 (m, 1H), 7.62 (t,1H),7.52 (d,1H,J=16Hz), 7.41-7.38 (m,2H),7.31 (t,1H),6.79 (d, 1H, J=16 Hz), 6.19 (m, 1H), 4.29 (d,2H),2.15(q,2H),1.01 (t,3H) la-279 3- C1, 4- F H 3-CF3 4-(-CONH-) 環丙基 HPLC-MS:logP = 3.33;質量 (m/z) : 509.1(M+H)+; 1HNMR (d6-DMSO) 9.42 (d, 1H), 8.55 (d, 1H), 8.00 (s, 1H), 7.90 (m, 2H), 7.65-7.60 (m, 2H), 7.55-7.50 (m, 2H), 6.93 (d, 1H, J=16 Hz), 6.05 (m, 1H), 2.75 (m, 1H), 0.70 (m, 2H), 0.50 (m, 2H) la-280 3- CF3, 4- F H 3-CF3 4-(-CONH-) 環丙基 HPLC-MS : logP = 3.46;質量 (m/z) : 543.1(M+H)+; 1HNMR (d6-DMSO) 9.50 (d, 1H), 8.55 (d, 1H), 8.12 (m, 1H), 8.05 (m, 1H), 8.00 (s, 1H), 7.92 (d, 1H), 7.67-7.60 (m, 2H), 7.54 (d, 1H), 6.93 (d, 1H, J=16 Hz), 6.19 (m, 1H), 2.78 (m, 1H), 0.70 (m, 2H), 0.50 (m, 2H) la-281 3- CFs, 4- F H 3-CF3 4-(-CON(C h3)-) 。比咬-2-基 HPLC-MS : logP = 3.63;質量 (m/z) : 594.03(M+H)+; 1HNMR (400 MHz, d3-CD3CN) : 8.30 (s, 1H, br), 7.90 (m, 2H), 7.83 (m, 1H), 7.75 (m, 2H), 7.70-7.50 (m, 5H, br), 231 201136518
No. (R')n R3 (R6)m A Y HPLC- MS a); *H NMR (δ > ppm) b) 7.41 (dd,1H),7.12 (s,1H,br),6·72 (d,1H,br),5.97 (m,1H),3.40 (s,3H, br) Ia-282 3- CF3, 4- F H H 4-(-CH2NH CO-) 乙基 HPLC-MS:logP = 3.11;質量 (m/z) : 476.99(M+H)+; 1HNMR (400 MHz, d6-DMSO) : 9.45 (d, 1H), 8.31 (t, 1H), 8.14 (d, 1H), 8.05 (m, 1H), 7.65 (t, 1H), 7.57-7.52 (m, 3H), 7.29 (d, 2H), 6.76 (d, 1H, J=16 Hz), 6.20 (m, 1H), 4.28 (d, 2H), 2.16 (q, 2H), 1.03 (t, 3H). la-283 3,4,5-Cl 3 H 3-CF3 4-(CONH-) 環丙基 HPLC-MS : logP = 4.1;質量(m/z): 559.1(M+H)+; 1HNMR (d6-DMSO) : 0.50 (m, 2H), 0.69 (m, 2H), 2.78 (m, 1H), 6.15 (p, 1H), 6.92 (d, 1H), 7.55 (d, 1H), 7.66 (d, 1H), 7.93 (br. d, 1H), 8.01 (m, 3H), 8.54 (d, 1H), 9.43 ppm(d, 1H). la-284 3-Br H 3-CF3 4-(CONH-) 環丙基 HPLC-MS : logP = 3.35;質量 (m/z) : 535(M+H)+; 1H NMR (d6-DMSO) : 0.50 (m, 2H), 0.69 (m, 2H), 2.78 (m, 1H), 6.01 (p, 1H), 6.95 (d, 1H), 7.42 (t, 1H), 7.54 (d, 1H), 7.65 (m, 3H), 7.87 (m, 1H), 7.91 (d, 1H), 7.99 (m, 1H), 8.54 (d, 1H), 9.40 (d, 1H). 表
b I 232 201136518 其中 R2、R3、R4 及 R5 分別為 Η,X 為 CF3 及 Q1、Q2、Q3、 (R、、(R6)m、A及Y分別如表2中之定義。數字2至6代 表芳香環上之位置。
No. (R!)n Q1 Q2 Q3 (R6)m A Y HPLC- MS a); *H NMR (δ > ppm)b) Ib-1 H CH CH N 3-CF3 4-(-CONH-) 苯甲基 HPLC-MS : logP = 3.02 質量 (m/z) : 509.0(M+H)+; 1H NMR (400 MHz, d6-DMSO) : 9.09 (t, 1H), 8.71 (m,2H),8.26(s, lH),8.17(d, lH),7.97(d,1H,J= 16Hz), 7.70-7.60 (m, 3H), 7.45 (m, 4H), 7.28 (m, 1H), 7.10 (d, 1H, J=16Hz), 6.73 (q, 1H), 4.46 (d, 2H) Ib-2 3-CF3 CH N CH 3-CF3 4-(-CONH-) 基 HPLC-MS : logP = 3.02 質量 (m/z) : 563.2(M+H)+; 1H NMR (400 MHz, d3-CD3CN) : 9.28 (s, 1H, br), 8.97 (m,2H),8.90 (d,1H),8_28 (m, 1H), 8.20 (m, 2H), 7.97 (m, 2H), 7.90 (d, 1H), 7.85 (m, 1H), 7.70-7.65 (m, 2H), 7.15 (dd, 1H), 6.82 (d, 1H, J=16Hz), 6.13 (m, 1H) Ib-3 3-CF3 CH N CH 3-CF3 4-(-CONH-) 環丙基 HPLC-MS : logP = 2.83;質量 (m/z) : 526.51(M+H)+; 1H NMR (400 MHz, d6-DMSO): 9.60 (d, 1H), 9.19 (s, 1H), 9.09 (s, 1H), 8.59 (d, 1H), 8.55 (s, 1H), 8.02 (s, 1H), 7.93 (dd, 1H), 7.67 (d, 1H, J=16Hz), 7.55 (d, 1H), 6.90 (d, 1H, J=16Hz), 6.38 (m, 1H), 0.70 (m, 2H), 0.50 (m, 2H) 233 201136518
No. (R^n Q1 Q2 Q3 (R6)m A Y HPLC- MSa); NMR (δ > ppm) b) Ib-4 3-CF3 CH N CH 3-CF3 4-(-CH2NHCO -) 環丙基 HPLC-MS:logP = 3.11;質量 (m/z) : 540.49(M+H)+; 1H NMR (400 MHz, d6-DMSO): 9.60 (d, 1H), 9.19 (s, 1H), 9.08 (s, 1H), 8.70 (m, 1H), 8.56 (s, 1H), 7.96 (s, 1H), 7.93 (dd, 1H), 7.64 (d, 1H), 7.54 (d, 1H), 6.88 (d, 1H, J=16Hz), 6.35 (m, lH),4.47(d, 1H), 1.70 (m, 2H), 0.70 (m, 4H) 234 201136518
其中 R2 及 R5 分別為 Η,X 為 CF3 及(R1;^,R3, V, (R6)m,A 及Y分別如表3中之定義。數字2至6或2至5代表芳香 環上之位置。
No. (R!)n R3 V (R6)m A Y HPLC- MS a); *H NMR (δ · ppm)b) Ic-1 3-CF3 H 0 H 3-CN 參見合成實例6,步驟1 Ic-2 3-CF3 H 0 H 3-(-S-) cf3 HPLC-MS:logP = 4.94;質量 (m/z): 488.0 (M+H)VH NMR (CD3CN) 6.13 (m, 1H), 7.60-7.90 (m, 5H), 7.97 - 7.98 (m, lH),8.15(m, 1H), 8.24-8.27 (m, 1H). Ic-3 3-CF3 H 0 H 4-CN HPLC-MS:logP = 3.72;質量 (m/z) : 413.1 (M+H)+; 'HNMR (CD3CN)6.13 (m, 1H), 7.57-8.05 (m, 8H), 8.33 - 8.35 (m, 1H). Ic-4 3-CF3 H NH H 3-CN HPLC-MS:logP = 3.48;質量 (m/z): 412.1 (M+H)VHNMR (CD3CN) 6.12 (m, 1H), 7.35 (s, 1H), 7.50 - 7.53 (m, 1H), 7.59-7.67 (m, 2H), 7.74-7.76 (m, 1H), 7.85-7.90 (m, 1H), 7.94 (m, 1H), 8.14 (m, 1H), 10.22 (s, 1H). 235 201136518
No. R3 V (R6)m A Y HPLC- MS a); 'H NMR (δ » ppm)b) Ic-5 3,4_C12 H 0 H 3-CN HPLC-MS:logP = 3.95;質量 (m/z) : 413.0 (M+H)+; 'HNMR (CD3CN) 5.99 (m, 1H), 7.51-7.53 (m, 1H), 7.58-7.61 (m, 2H),7.72 - 7.80 (m,3H), 8.03 - 8.05 (m, 1H), 8.16 (m, 1H). Ic-6 3-CF3 H 0 H 3-(-CONH-) H HPLC-MS:logP = 2.69;質量 (m/z): 431 · 1 (M+H)VH NMR (CD3CN) 6.03 (br. s, 1H), 6.13 (m, 1H), 6.81 (br. s, 1H), 7.63 - 7.99 (m,7H),8.24 -8.25 (m, 2H). Ic-7 2,4-Cl2 H 0 H 3-CN HPLC-MS:logP = 4.04;質量 (m/z) : 413.0 (M+H)+; NMR (CD3CN) 6.48 (m, 1H), 7.48 -7.50 (m, 1H), 7.62-7.63 (m, 2H), 7.74 - 7.82 (m, 3H), 8.19-8.22 (m, 2H). Ic-8 3-CF3 H NH H 4-CN HPLC-MS:logP = 3.51;質量 (m/z): 412.0 (M+H)VHNMR (CD3CN) 6.16 (quint, 1H), 7.33 - 7.40 (m, 2H), 7.63 -7.69 (m, 2H), 7.77 - 7.79 (m, 1H), 7.84-7.97 (m, 3H), 8.07-8.09 (m, 1H), 10.34 (s, 1H). Ic-9 3-CF3 H NH 5-SO 2CH3 3-(-S〇2-) ch3 HPLC-MS:logP = 2.92;質量 (m/z) : 465.0 (M+H)+; 'H NMR (CD3CN) 3.05 (s,3H),6.13 (quint, 1H), 7.43 - 7.44 (m, 1H), 7.64-7.68 (m, 2H), 7.75 - 7.78 (m, 2H), 7.86 -7.88 (m, 1H), 7.95-8.00 (m, 2H),8.34(m, 1H), 10.10 (s, 236 201136518
No. (R1)- R3 V (R6)m A Y HPLC- MS a); *H NMR (δ > ppm) b) 1H). Ic-10 3-CF3 H 0 H 3-(-CH2NHC 0-) ch3 參見合成實例6,步驟3 Ic-11 3-C1, 5-CF3 H NH H 3-CN HPLC-MS:logP = 3.90;質量 (m/z) : 446.0 (M+H)+; 'HNMR (CD3CN) 6.16 (quint, 1H), 7.37-7.38 (m, 1H), 7.53-7.55 (m, 1H), 7.61-7.64 (m, 1H), 7.82 (s, 1H), 7.91-7.93 (m, 1H), 8.03 -8.05 (m, 1H), 8.17-8.18 (m, 1H), 10.34 (s, 1H). Ic-12 3-CFs H 0 H 3-(-CH2NHC 0-) 基 HPLC-MS : logP = 3.62;質量 (m/z): 522.1 (M+H)VH NMR (CD3CN)4.69 (d, 2H), 6.13 (quint, 1H), 7.49 - 7.56 (m, 3H), 7.64- 7.78 (m, 3H), 7.87-7.98 (m, 3H), 8.11-8.13 (m, 1H), 8.19-8.22 (m, 1H), 8.56-8.59 (m, 1H), 8.69 (br. s,1H)· Ic-13 3-CF3 H 0 H 3-(-CH2NHC 0-) 2-丙烯 -1-基 HPLC-MS :logP = 3.24;質量 (m/z): 485.1 (M+H)VH NMR (CD3CN) 1.77- 1.83 (m,lH), 2.97-2.99 (m, 1H), 4.42 (d, 1H), 4.47 (d, 2H), 5.11 -5.19 (m, 1H), 5.92-6.01 (m, 1H), 6.13 (quint, 1H), 6.72-6.77 (m, 1H), 6.90 (br. s, 1H), 7.39 - 7.42 (m, 1H), 7.50- 7.55 (m, 2H), 7.61 -7.69 (m, 2H), 7.76 - 7.78 (m, 1H),7.88- 237 201136518
No. (R1)- R3 V (R6)m A Y HPLC- MS a); *H NMR (δ » ppm) b) 7.90 (m, 1H), 7.97 - 7.99 (m, 1H), 8.21-8.23 (m, 1H). Ic-14 3-CF3 H 0 H 3-(-CH2NHC 0-) 乙基 HPLC-MS:logP = 3.09;質量 (m/z) : 473.1 (M+H)+; 'HNMR (d6-DMSO) 1.03 (t,3H), 2.15. (q, 2H), 4.36 (d, 2H), 6.30 (quint, 1H), 7.38-7.41 (m, 1H), 7.66-7.83 (m, 5H), 8.06-8.08 (m, 1H), 8.24 (s, 1H), 8.32 - 8.35 (m, 1H), 9.93 - 9.95 (m, 1H). Ic-15 3-CFa H NH H 4-CN HPLC-MS:logP = 3.57;質量 (m/z):430.1 (M+H)+; 'HNMR (CD3CN) 6.15 (quint, 1H), 7.36 - 7.39 (m, 2H), 7.65- 7.69 (m, 1H), 7.76-7.78 (m, 1H), 7.87-7.89 (m, 1H), 7.97 (m, 1H), 8.05-8.08 (m, 1H), 8.13-8.15 (m, 1H), 10.41 (s, 1H). Ic-16 3-CF3 H 0 6-F 3-(-CONH-) H HPLC-MS:logP = 2.88;質量 (m/z): 449.1 (M+H)VH NMR (CD3CN) 6.12 (quint, 1H), 6.32 (br. s, 1H), 6.77 (br. s, 1H), 7.48 (d, 1H), 7.61 (s, 1H), 7.65-7.69 (m, 1H), 7.77-7.79 (m, 1H), 7.98 (m, 1H), 8.22 - 8.29 (m, 2H). Ic-17 3-CF3 H NH H 3-(S〇2-) CF3 HPLC-MS:logP = 4.19;質量 (m/z): 517.1 (M+H)VHNMR (CD3CN) 6.13-6.19 (m, 1H), 7.55 (s, 1H), 7.66-7.70 (m, 1H), 7.77-7.90 (m, 3H), 7.98 (s,1H),8.23 (br.s,1H),8.58- 238 201136518
No. (R1)- R3 V (R6)m A Y HPLC- MS a); *H NMR (δ · ppm) b) 8.59 (m, 1H), 10.69 (s, 1H). Ic-18 3-CF3 H NH 5-C1 4-(-CONH-) 環丙基 HPLC-MS : logP = 2.98;質量 (m7z) : 504.02; 1HNMR (d6-DMSO) 11.80 (s, 1H), 9.50 (s, 1H, br),8.63 (d, 1H), 7.99 (s, 1H), 7.89 (d, 1H), 7.75 (m, 2H), 7.67 (t, 1H), 7.51 (s, 1H), 7.30 (s, 1H), 6.15 (m, 1H), 2.88 (m, 1H), 0.81 (m, 2H), 0.64 (m, 2H). Ic-19 3-CF3 H 0 H 4-(-CONH-) 環丙基 參見合成實例7,步驟6 Ic-20 3-CF3> 5-C1 H NH 5-C1 4-(-CONH-) 環丙基 HPLC-MS :logP = 3.47;質量 (m/z) : 537.98; 1H NMR (400 MHz, d6-DMSO) : 9.64 (d, 1H), 8.44 (d, 1H), 8.30-8.20 (m, 3H), 7.99 (s, 1H), 7.84 (s, 1H), 7.50 (s, 1H), 7.41 (s, 1H), 6.42 (m, 1H), 2.82 (m, 1H), 0.70 (m, 2H), 0.50 (m, 2H). Ic-21 3,4-Cl2 H NH 5-C1 4-(-CONH-) 環丙基 HPLC-MS :logP = 3.28;質量 (m/z) : 505.91 Ic-22 3,5-Cl2 H NH 5-C1 4-(-CONH-) 環丙基 HPLC-MS : logP = 3.42;質量 (m/z) : 505.95; 1H NMR (400 MHz, d6-DMSO) : 9.55 (d, 1H), 8.44 (d, 1H), 8.30-8.20 (m, 2H), 7.92 (s, 1H), 7.83 (s, 1H), 7.75 (m, 1H), 7.49 (s, 1H), 7.41 (s, 1H), 6.29 (m, 1H), 2.82 (m, 1H), 0.70 (m, 239 201136518
No. (R!)n R3 V (R6)m A Y HPLC- MS a); *H NMR (δ > ppm) b) 2H), 0.50 (m, 2H). Ic-23 3-CF3 H NH 6-C1 3-(-CONH-) 。比啶-2-基甲基 HPLC-MS:logP = 2.49;質量 (m/z): 555.1 (M+H)VHNMR (CD3CN) 4.65 - 4.66 (m, 2H), 6.15 (quint, 1H), 7.24-7.27 (m, 1H), 7.32 (s, 1H), 7.43 -7.50 (m, 2H), 7.57 (s, 1H), 7.69-7.67 (m, 1H), 7.73-7.78 (m, 2H), 7.81-7.97 (m, 3H), 8.07 - 8.09 (m, 1H), 8.53 -8.55 (m, 1H), 10.19 (s, 1H). Ic-24 3-CF3 H NH 6-C1 3-(-CONH-) 環丙基 See Sythesis 實例 8,步驟 4 Ic-25 3-CF3 H N-Me 3-C1 3-(-CONH-) 環丙基 HPLC-MS : logP = 3.5;質量 (m/z) :518.1 (M+H)+; 1H NMR (CD3CN) 0.58 - 0.61 (m, 2H), 0.74-0.78 (m, 2H), 2.84-2.87 (m, 1H),3.93 (s, 3H), 6.15 (m, 1H), 6.83 (m, 1H), 7.21 (s, 1H), 7.56 (s, 1H), 7.67-7.78 (m, 3H), 7.88 - 7.90 (m, 1H), 7.97 (s, 1H), 8.08-8.10 (m, 1H). Ic-26 3-CF3 H N-Et 3-C1 3-(-CONH-) 環丙基 HPLC-MS : logP = 3.8;質量 (m/z) : 532.2(M+H)+; 1H NMR (CD3CN) 0.58 - 0.60 (m, 2H), 0.75-0.78 (m, 2H), 1.27 (t, 3H), 2.85 - 2.87 (m, 1H), 4.45 (q, 2H), 6.14 (quint, 1H), 6.84 (m, 1H), 7.17 (s, 1H), 7.54 (s, 1H), 7.66 - 7.69 (m, 1H), 7.72 240 201136518
No. (R!)n R3 V (R6)m A Y HPLC- MS a); 'H NMR (δ > ppm) b) (s, 1H), 7.77-7.79 (m, 1H), 7.90-7.92 (m, 1H), 7.99 (s, 1H), 8.23 -8.25 (m, 1H). Ic-27 3-CF3 H N-CH2O Et 3-C1 3-(-CONH-) 環丙基 HPLC-MS:logP = 3.81;質量 (m/z) : 562.2(M+H)+; 1H NMR (CD3CN) 0.58 - 0.61 (m, 2H), 0.75 - 0.78 (m, 2H), 0.99 (t, 3H), 2.84 — 2.89 (m, 1H), 3.29-3.37 (m, 2H), 5.78 (s, 1H), 6.09-6.14 (m, 1H), 6.91- 6.92 (m, lH),7.18(s, 1H), 7.51 (s, 1H), 7.66-7.70 (m, 2H), 7.77-7.79 (m, 1H), 7.91- 7.92 (m, 1H), 7.98 (s, 1H), 8.53 (d, 1H). Ic-28 3-CF3 H N-CH2P h 3-C1 3-(-CONH-) 環丙基 HPLC-MS:logP = 4.25;質量 (m/z) : 594.2(M+H)+; 1H NMR (CD3CN) 0.56 - 0.59 (m, 2H), 0.74 - 0.77 (m, 2H), 2.83 -2.86 (m, 1H),5.70 (s, 2H), 6.08 (quint, 1H), 6.83 (s, 1H), 6.97-7.00 (m, 2H), 7.16-7.21 (m, 3H), 7.28 (s, 1H), 7.49 (s, 1H), 7.63 - 7.66 (m, 1H), 7.76 - 7.77 (m, 2H), 7.82 -7.84 (m, 1H), 7.93 (s, 1H), 8.18 (d, 1H). Ic-29 3-CF3 H it 丙-2-稀-1-基 3-C1 3-(-CONH-) 環丙基 HPLC-MS:logP = 3.86;質量 (m/z) : 544.1(M+H)+; 1H NMR (CD3CN) 0.58 - 0.59 (m, 2H), 0.75-0.77 (m, 2H), 1.93- 1.97 (m, 1H), 4.73-4.76 (m, 1H), 5.00-5.02 (m, 1H), 5.07-5.08 (m, 2H),5.89- 5.97 (m, 1H), 6.10 (quint, 1H), 241 201136518
No. (R*)n R3 V (R6)m A Y HPLC- MSa); lH NMR (δ > ppm) b) 6.87 (s, 1H), 7.22 (s, 1H), 7.49 (s, 1H), 7.66-7.68 (m, 1H), 7.74 (s, 1H), 7.77-7.78 (m, 1H), 7.88-7.90 (m, 1H), 7.97 (s, 1H), 8.23 (d, 1H). Ic-30 3-CF3 H N-Me 3-C1 3-(-CONH-) 曱基 HPLC-MS:logP = 3.2;質量 (m/z) : 492.1(M+H)+;)+; 1H NMR (CD3CN) 2.89 (d, 3H), 3.88 (s, 3H), 6.12 (quint, 1H), 6.74-6.75 (m, 1H), 7.10 (s, 1H), 7.44 (s, 1H), 7.66-7.69 (m, 2H), 7.77-7.79 (m, 1H), 7.92-7.93 (m, 1H), 8.04 (s, lH),8.54(d, 1H). Ic-31 3-CF3 H N-Me 3-C1 3-(-CONH-) 丁-3-炔 -2-基 HPLC-MS:logP = 3.73;質量 (m/z) : 530.1(M+H)+; 1H NMR (CD3CN) 1.47 (d, 3H), 2.57 (d, 1H),3.92 (s, 3H), 4.88-4.93 (m, 1H), 6.13 (quint, 1H), 7.11 (d, 1H), 7.21 (s, 1H), 7.55 (s, 1H), 7.65-7.67 (m, 1H), 7.75 - 7.79 (m, 2H), 7.88 -7.91 (m, 1H), 7.98 (s, 1H),8.17 (d, 1H). Ic-32 3-CF3 H N-Me 3-C1 3-(-CONH·) 丙-2·稀 -1-基 參見合成實例12,步驟2 Ic-33 3-CF3 H N-Me 3-C1 3-(-CONH-) 硫雜環 丁-3-基 HPLC-MS:logP = 3.82;質量 (m/z) : 550(M+H)+; 1HNMR (CD3CN) 3.34 - 3.37 (m,2H), 3.51-3.54 (m, 2H), 3.93 (s, 3H), 5.29-5.34 (m, 1H), 6.13 (quint, 1H), 7.21 (s, 1H), 7.37 (d, 1H), 7.57 (s, 1H), 7.66-7.69 (m, 1H), 7.77-7.79 (m, 242 201136518
No. (R\ R3 V (R6)m A Y HPLC- MS a); JH NMR (δ > ppm) b) 2H), 7.89-7.90 (m, 1H), 7.98 (s, 1H), 8.14 (d, 1H). Ic-34 3-CF3 H N-CH2-〇-苯曱 基 3-C1 3-(-CONH-) 環丙基 HPLC-MS:logP = 4.31;質量 (m/z) : 624.2(M+H)+; 1H NMR (CD3CN) 0.58 - 0.60 (m, 2H), 0.75-0.78 (m, 2H), 2.83-2.88 (m, 1H), 4.36-4.42 (m, 2H)} 5.91 - 5.95 (m, 2H),6.12 (quint, 1H), 6.87 (s, 1H), 7.10-7.14 (m, 2H), 7.20-7.27 (m, 4H), 7.63 - 7.66 (m, 2H), 7.75 - 7.78 (m, 2H), 7.85-7.86 (m, 1H), 7.95-7.97 (m, 1H), 8.26 (d, 1H). Ic-35 3-CF3 H n-ch2-c OOMe 3-C1 3-(-CONH-) 環丙基 HPLC-MS:logP = 3.42;質量 (m/z) : 576.1(M+H)+; 1H NMR (CD3CN) 0.56 - 0.60 (m, 2H), 0.74 - 0.79 (m, 2H), 2.83 -2.88 (m, 1H),3.63 (s, 3H),5.19 (s, 2H), 6.07 (quint, 1H), 6.84 (s,1H),7.34 (s,1H),7.55 (s, 1H), 7.65-7.68 (m, 1H), 7.76 - 7.79 (m, 2H), 7.85 -7.87 (m, 1H), 7.95 (s, 1H),8.10 (d, 1H). Ic-36 3-CF3 H N-CH2-C N 3-C1 3-(-CONH-) 環丙基 HPLC-MS:logP = 3.29;質量 (m/z) : 543.1(M+H)+; 1H NMR (CD3CN) 0.58 - 0.60 (m, 2H), 0.76 - 0.78 (m, 2H), 2.85 -2.86 (m, 1H),5.48 (s, 2H), 6.15 (quint, 1H), 6.89 (s, 1H), 7.40 (s, 1H), 7.67-7.69 (m, 2H), 7.77-7.81 (m, 2H),7.90-7.91 (m, 1H), 7.99 (s, 1H), 8.24 243 201136518
No. (R*)n R3 V (R6)m A Y HPLC- MSa); *H NMR (6 » ppm)b) (d, 1H). Ic-37 3-CF3 H n-ch2- 乙炔基 3-C1 3-(-CONH-) 環丙基 HPLC-MS:logP = 3.59;質量 (m/z) : 542.1 (M+H)+; 1H NMR (CD3CN) 0.57 - 0.60 (m, 2H), 0.75-0.78 (m, 2H),2.51 (t, 1H), 2.84-2.87(m, 1H), 5.32 (d, 2H), 6.14 (quint, 1H), 6.86 (s, 1H), 7.27 (s, 1H), 7.62 (s, 1H), 7.66 - 7.69 (m, 1H), 7.76 - 7.79 (m, 2H), 7.89 -7.91 (m, 1H), 7.98 (s, 1H), 8.22 (d, 1H). Ic-38 3-CF3 H n-ch2- 乙炔基 3-C1 3-(-CONH-) 環丙基 HPLC-MS:logP = 2.59;質量 (m/z) : 561.2(M+H)+; 1H NMR (CD3CN) 0.56 - 0.60 (m, 2H), 0.74 - 0.79 (m, 2H), 2.83 -2.87 (m, 1H), 5.07 (s, 2H), 5.81 (s, 1H), 6.10 (quint, 1H), 6.33 (s, 1H), 6.86 (s, 1H), 7.30 (s, 1H), 7.52 (s, 1H), 7.65 - 7.70 (m, 1H), 7.76-7.78 (m, 2H), 7.86-7.88 (m, 1H), 7.96 (s, 1H), 8.22 (d, 1H). Ic-39 3-CF3 H N-CH2-C (0)NH2 3-C1 3-(-CONH-) 丙烧-2· 基 HPLC-MS : logP = 4.07;質量 (m/z) :534.1 (M+H)+; 1H NMR (CD3CN) 1.22 (d, 6H), 1.28 (t, 3H), 4.13-4.18 (m, 1H), 4.47 (q, 2H), 6.13 (quint, 1H), 6.64 (d, 1H), 7.21 (s, 1H), 7.58 (s, 1H), 7.65-7.69 (m, 1H), 7.75 - 7.79 (m, 2H), 7.88 -7.90 (m, 1H), 7.98 (s, 1H), 8.13 (d, 1H). 244 201136518
No. (R1)- R3 V (R6)m A Y HPLC- MS a); *H NMR (δ > ppm) b) Ic-40 3-CF3 H N-Et 3-C1 3-(-CONH-) 環丁基 HPLC-MS : logP = 4.22;質量 (m/z):546.1(M+H)+; 1HNMR (d6-DMSO) 1.20 (t, 3H), 1.65-1.71 (m, 2H), 1.99-2.07 (m, 2H), 2.22 - 2.27 (m, 2H), 4.35-4.41 (m, 1H), 4.51 (q, 2H), 6.29 (quint, 1H), 7.36 (s, 1H), 7.64-7.87 (m, 4H), 8.04-8.06 (m, 1H), 8.20 (s, 1H), 8.55 (d, 1H), 9.78 (d, 1H). Ic-41 3-CF3 H N-Et 3-C1 3-(-CONH-) 2,2-二氟 -乙基 HPLC-MS :logP = 3.87;質量 (m/z) : 556.1(M+H)+; 1H NMR (CD3CN) 1.29 (t, 3H), 3.73 -3.79 (m, 2H), 4.47 (q, 2H), 5.95-6.17m, 2H), 7.09-7.11 (m, 1H), 7.21 (s, 1H), 7.60 (s, 1H), 7.66-7.69 (m, 1H), 7.77 - 7.79 (m, 1H), 7.81 (s, 1H), 7.89-7.90 (m, 1H), 7.98 (s, lH),8.16(d, 1H). Ic-42 3-CF3 H N-Et 3-C1 3-(-CONH-) 丁-3-炔 -2-基 HPLC-MS : logP = 3.99;質量 (m/z) : 544.1(M+H)+; 1H NMR (CD3CN) 1.29 (t, 3H), 1.47 (d, 3H), 2.56-2.57 (m, 1H), 4.48 (q, 2H), 4.87-4.94 (m, 1H), 6.13 (quint, 1H), 7.09-7.12 (m, 1H),7.23 (s, 1H),7.62 (s, 1H), 7.65 - 7.69 (m, 1H), 7.77 - 7.79 (m, 2H), 7.88 -7.89 (m, 1H), 7.97 (s, 1H), 8.08 (d,1H). Ic-43 3-CF3 H N-Et 3-C1 3-(-CONH-) 吡咬-2- 基 HPLC-MS : logP = 4.22;質量 (m/z) : 569.1 (M+H)+; 1H NMR (CD3CN) 1.31 (t, 3H), 4.50 (q, 2H), 6.15 (quint, 1H),7.11- 245 201136518
No. (R^n R3 V (R6)m A Y HPLC- MSa); *H NMR (6 · ppm) b) 7.14 (m, 1H), 7.27 (s, 1H), 7.66 - 7.70 (m, 2H), 7.77 -7.90 (m, 3H), 7.97-7.99 (m, 2H),8.09 (d, 1H), 8.28-8.31 (2H), 9.07 (s, 1H). Ic-44 3-CF3 H N-Et 3-C1 3-(-CONH-) 環丙基 HPLC-MS:logP = 4.31;質量 (m/z):546.1(M+H)+; 1HNMR (CD3CN) 0.37 - 0.38 (m, 2H), 0.50-0.53 (m, 2H), 1.30 (t, 3H), 2.68-2.70 (m, 1H), 3.06 (s, 3H), 4.49 (q, 2H), 6.14 (quint, 1H), 7.21 (s, 1H), 7.59 -7.69 (m, 3H), 7.77 - 7.79 (m, 1H), 7.87-7.89 (m, 1H), 7.97 (s, 1H), 8.06 (d, 1H). Ic-45 3-CF3 H NH 3-C1 3-(-CONH-) 0比咬-2-基 HPLC-MS:logP = 3.37;質量 (m/z) :541.1 (M+H)+; 1H NMR (CD3CN) 6.16 (quint, 1H), 7.11-7.14 (m, 1H), 7.35 (m, 1H), 7.59 (s, 1H), 7.65 - 7.69 (m, 1H), 7.76-7.97 (m, 3H), 8.00 (s, 1H), 8.04 (s, 1H) 8.04 (d, 1H), 8.28-8.31 (m, 2H), 9.10 (m, 1H), 10.19 (s, 1H). Ic-46 3-CFj H NH 3-C1 4-(-CONH-) 0比咬-2-基甲基 HPLC-MS:logP = 2.5;質量 (m/z) : 555.12(M+H)+; 1H NMR (d3-CD3CN) 10.4 (s, 1H), 8.55 (s, lH,br), 8.20 (d, 1H), 7.98 (s, 1H), 7.88 (dd, 1H), 7.80-7.75 (m, 3H), 7.70-7.65 (m, 2H), 7.55 (s, 1H), 7.48 (s, 1H), 7.25 (m, 2H), 6.15 (m, 1H), 4.56 (d, 2H) 246 201136518
No. (RX)n R3 V (R6)m A Y HPLC- MS a); *H NMR (δ « ppm) b) Ic-47 3-CF3 H NH 3-C1 4-(-CONH-) 2,2-二 敗乙基 Ic-48 3-CF3 H N-Me 3-C1 4-(-CONH-) 環丙基 HPLC-MS:logP = 3.33;質量 (m/z) : 518.38(M+H)+; 1H NMR (400 MHz, d3-CD3CN): 8.20 (d, 1H), 7.99 (s, 1H), 7.90 (d, 1H), 7.78 (d, 1H), 7.70 (m, 2H), 7.55 (s, 1H), 7.10 (s, 1H), 6.89 (s,1H), 6.13 (m, 1H),3.94 (s,3H),2.86(m,lH),0.77(m, 2H), 0.60 (m, 2H)
其中 R2、R3、R4 分別為 Η,及 X、(R、、R5、(R6)m、A 及 Y分別如表4中之定義。數字2至6代表芳香環上之位置。
No. (Ri)n X R5 (R6)m A Y HPLC- MS a); JH NMR (δ > ppm) b) Id-1 3-CF3 CF2(CH3) H 3-C1 4-(-CONH-) 環丙基 參見合成實例14,步驟2 Id-2 3-F chf2 H 3-CF3 4-(-CONH-) 環丙基 HPLC-MS : logP = 2.68; 質量(m/z) : 457.1(M+H)+; 1HNMR (d6-DMSO) 0.50 (m, 2H), 0.71 (m, 2H), 2.79 (m, lH),5.56(m, 1H), 6.33 247 201136518
No. (R*)n X Rs (R6)m A Y HPLC- MSa); *H NMR (δ » ppm)b) (m,1H),6.98 (d,1H),7.20 (m, 1H), 7.33-7.66 (m, 5H), 7.89 (m, 1H), 7.97 (s, 1H),8.54 (d, 1H), 9.07 (d, 1H). Id-3 3-C1 chf2 H 3-CF3 4-(-CONH-) 環丙基 HPLC-MS : logP = 2.92; 質量(m/z) : 473.1(M+H)+; 1HNMR (d6-DMSO) 0.50 (m, 2H), 0.69 (m, 2H), 2.80 (m, 1H), 5.55 (m, 1H), 6.33 (m, 1H), 6.99 (d, 1H), 7.44 (m, 3H), 7.53-7.62 (m, 3H), 7.90 (m, 1H), 8.01 (m, 1H), 8.54 (d, 1H), 9.08 (d, 1H). Id-4 3-CF3 cf3 ch3 3-CF3 4-(-CONH-) 丙炫τ2·基 HPLC-MS : logP-3.75; 質量(m/z) : 541.4(M+H)+; lHNMR(d3-CD3CN) 7.88 (m, 2H), 7.80-7.75 (m, 4H), 7.68-7.63 (t, 1H), 7.50 (d, 1H), 6.74 (d, 1H, br), 6.35 (s, lH),5.99(m, 1H), 4.10 (d, 2H), 1.94 (m, 3H), 1.20 (d,6H) 表5
248 201136518 八中=、R、R4及R5分別為H,X為CF3及(R、、R13 及γ分別如表5中之^義。數字2至6代表芳香環上之位
No. (R')„ R13 Y HPLC- MSa); NMR (δ,ppm) b> Ie-1 3-CF3 H 甲基 參見合成實例15,步驟6 Ie-2 3-CF3 H 環丙基曱基 HPLC-MS : logP = 3.54;質量(m/z): 511,2(M+H)+; 1H NMR (d6-DMSO) 0.15 (m, 2H), 0.47 (m, 2H), 1.02 (m, 1H), 1.80 (m, 1H), 2.04 (d, 2H), 2.41 (m, 1H), 2.73 (m, 1H), 2.94 (m, 1H), 5.29 (q, 1H), 6.14 (m, 1H), 6.80 (d, 1H), 7.23 (d, 1H), 7.45 (d, 1H), 7.47 (s, 1H), 7.54 (d, 1H), 7.71 (t, 1H), 7.81 (d, 1H), 7.94 (d, 1H), 8.04 (s, 1H), 8.09 (d, 1H), 9.40 (d, 1H). Ie-3 3-CFs H — 乙基 ~~-- HPLC-MS : logP = 3.27;質量(m/z): 585.2(M+H)+; lHNMR(d6-DMSO) 1.05 (t, 3H), 1.79 (m, 1H), 2.13 (m, 2H), 2.38 (m, 1H), 2.82 (m, 1H), 2.94 (m, 1H), 5.28 (q, 1H), 6.14 (m, 1H), 6.80 (d, 1H), 7.22 (d, 1H), 7.44 (d, 1H), 7.47 (d, 1H), 7.54 (d, 1H), 7.71 (t, 1H), 7.81 (d, 1H), 7.94 (d, 1H), 8.05 (s, 1H), 8.13 (d, 1H), 9.42 (d, 1H). 表6
其中 R、R3、R4 及 R5 分別為 H,X 為 CF3&Q4、Q5、(Ri)n、 249 201136518 (R6)m、A及Y分別如表6中之定義。數字2至6代表芳香 環上之位置。
No. (R^n Q4 Q5 (R6)m A Y HPLC- MSa); lU NMR (δ « ppm) b) If-1 3-CF3 CH N H 4-(-CH2NHC 0-) 環丙基 HPLC-MS : logP = 2.44;質量 (m/z) : 472.07(M+H)+; 1HNMR (400 MHz, d3-CD3CN) : 8.52 (d, 1H), 8.01-7.99 (m, 2H), 7.81 (d, 1H), 7.76 (d, 1H), 7.70-7.65 (m, 2H), 7.60 (d, 1H, J=16Hz), 7.45 (d, 1H), 7.14 (d, 1H, J=16Hz), 7.08 (s, 1H, br), 6.00 (m, 1H), 4.36 (d, 2H), 1.50 (m, 1H), 0.70 (m, 2H), 0.80 (m, 2H) If-2 3-CF3 N CH 3-CF3 4-(-CONH-) 環丙基 參見合成實例11,步驟3 If-3 3-CF3 N CH H 4-(-CH(CH3) NHCO-) 環丙基-曱基 HPLC-MS : logP = 3;質量(m/z): 500.15(M+H)+; 1H NMR (400 MHz, d6-DMSO) : 9.56 (d, 1H), 8.73 (s, 1H), 8.25 (d, lH),8.07(s, 1H), 7.98 (d, 1H), 7.95 (d, 1H), 7.80 (d, 1H), 7.70 (m, 1H), 7.69 (d, 1H, J=16Hz), 7.39 (dd, 1H), 6.87 (d, 1H, J=16 Hz), 6.18 (m, 1H), 4.95 (m, 1H), 2.05 (d, 2H), 1.36 (d, 3H), 0.95 (m, 1H), 0.43 (m, 1H), 0.13 (m, 1H) 表7 250 201136518
(ig) 其中 R2、R3、R4 及 R5 分別為 Η,X 為 CF3 及(Ri)n、(R6)m、 A及Y分別如表7中之定義。數字2至6代表芳香環上之 位置。
No. (R*)n (R6) m A Y HPLC- MS 1; JH NMR (δ * ppm) 2 Ig-1 3-CF3 3-Cl 4-(-CONH-) 環丙基 參見合成實例13,步驟3 251 1 M+係由LC-MS在pH 2.7之酸性範圍内測定;以乙腈(包 含0.1°/。曱酸)及水作為溶離劑;線性梯度自1〇%乙腈至95〇/〇 乙猜,儀器.Agilent 1100 LC-System,Agilent MSD System, HTS PAL。 上表及製備實例中所示logP值係依據EEC Directive 79/831 Annex V.A8,利用HPLC (高效液相層析法),於逆相 管柱(C18)上測定。溫度43°C。採用具有已知logP值之未 分支之烷-2-酮類(具有3至16個碳原子)進行校正。 2 HNMR數據係採用BrukerAvance 400,以四曱基石夕院為 參考物(0.0)及溶劑CD3CN、CDC13、[D6]-DMSO測定。訊號 刀裂特徵係以s =單峰,br.s =寬單峰,d=雙峰’ 參峰,q 201136518 =肆峰,quint 五峰,m ==多峰,dd=雙重雙峰表示 應用實例 下列實例出示本發明化合物之殺昆蟲及殺壁 (例===表關' 至”以相應之參考代號 實例1 : 牛碑(Boophilus microplus)試驗(BOOPMI 注射法) 溶劑:二曱亞砜 製備活性成份調配物時,由10 mg活性成份與〇 5 ml 溶劑混合’以水稀釋該濃縮物至所需濃度。取活性成份溶 液注射至牛蜱mz.crop/ws)腹部,將動物移至培養 皿上,保存在氣候控制室中。由產下之可粹化蟲卵數評估 效力。 7天後,測定效力%。100%表示沒有牛碑可孵化之愚 卵。 本試驗中,下列本發明化合物具有所示之效力: 在20pg/隻動物之施用率下之效力為1〇〇% : la-5、la-8、la-22、la-23、la-24、la-29、la-30、la-3 卜 la-32、 la-40、la-41、la-42、la-43、la-44、la-45、la-46、la-58、 la-60、la-73、la-76、la-77、la-80。 實例2 : 252 201136518 薄田櫛頭蛋(Ctenocephalides felis) 口服(CTECFE) 溶劑:1份重量比之二曱亞颯 製備活性成份調配物時,由1〇 活性成份與〇·5 ml 二曱亞砜混合。取一部份濃縮物,以經過檸檬酸鹽處理之 牛血稀釋,製備所需濃度。 取20又未链食之跳蛋成蟲(描褐頭蛋印/ 片/⑷)置入上下兩面均以紗布密封之容器中。取一個底部已 以石蠟膜(Parafilm)密封之金屬量筒置於該容器上方。該量 筒包含血液-活性成份製劑,跳蚤可透過石躐膜吸食。 2天後,測定死亡率%。1〇〇%表示所有跳蚤死亡;〇% 表不沒有跳蛋死亡。 本試驗中,下列本發明化合物具有所示之效力: 在20 ppm之施用率下之效力為95% : la-73; la-31 本試驗中,下列本發明化合物具有所示之效力: 在20 ppm之施用率下之效力為98% : la-45; la-58 本試驗中,下列本發明化合物具有所示之效力: 在20 ppm之施用率下之效力為1〇〇〇/0: la-22、la-23、la-24、la-30、la-32、la-40、la-41、la-42、 la-43、la-60、la-80 實例3 綠蠅(Lucilia cuprina)試驗(LUCICU) 253 201136518 溶劑:二曱亞砜 製備活性成份調配物時’由1〇 mg活性成份與〇 5 二曱亞碾混合’以水稀釋該濃縮物至所需濃度。在包含經 過所需濃度之活性成份調配物處理之馬肉之容器中接種綠 織(Lucilia cuprina)幼蟲ί。 2天後’測定死亡率%。100%表示所有幼蟲均死亡; 0%表示沒有幼蟲死亡。 本試驗中’下列本發明化合物具有所示之效力: 在20 ppm之施用率下之效力為80% : la-24 本S式驗中’下列本發明化合物具有所示之效力: 在20 ppm之施用率下之效力為90% : la-22、la-40、la-41、la-60 本s式驗中,下列本發明化合物具有所示之效力: 在20卩卩111之施用率下之效力為1〇〇〇/0: la-23、la-30、la-42、la-43、la-45 實例4 家蠅(Musca domestica)試驗(MUSCDO) 溶劑:二曱亞礙 製備活性成份調配物時,由1〇 mg活性成份與0 5 ml 一曱亞礙混合,以水稀釋該濃縮物至所需濃度。在包含經 過所需濃度之活性成份調配物處理之海綿之容器中接種家 绳对/μ)成蟲。 254 201136518 2天後,測定死亡率%。100%表示所有家蠅均死亡; 〇%表示沒有家蠅死亡。 本試驗中,下列本發明化合物具有所示之效力: 在20 ppm之施用率下之效力為85% : la-30 實例5 赤财(Myzus)試驗(MYZUPE噴灑處理) 溶劑: 78份重量比丙酮 1.5份重量比二曱基曱醯胺 乳化劑:0.5份重量比烷基芳基聚二醇醚 製備活性成份調配物時,由1份重量比活性成份與上 述量溶劑及乳化劑混合,以含乳化劑之水稀釋該濃縮物至 所需濃度。在受到所有階段桃赤財(Myzus persicae)感染之 捲心白菜(Brassica pekinensis)葉圓片上喷灑所需濃度之活 性成份調配物。 6天後,測定效力%。1〇〇%表示所有对蟲均死亡;〇% 表示沒有财蟲死亡。 本試驗中’下列本發明化合物具有所示之效力: 在20g/ha之施用率下之效力為80〇/〇 : la-75 本试驗中’下列本發明化合物具有所示之效力: 在20 g/ha之施用率下之效力為9〇〇/0 : la-115 255 201136518 本試驗中,下列本發明化合物具有所示之效力: 在20 g/ha之施用率下之效力為100% : la-41;la-112 實例6 草地黏蟲(Spodoptera frugiperda)試驗(SPODFR喷濃處理) 溶劑: 78.0份重量比丙酮 1.5份重量比二曱基曱醯胺 乳化劑:份重量比烧基芳基聚二醇趟 製備活性成份調配物時,由1份重量比活性成份與上 述量溶劑及乳化劑混合,以含乳化劑之水稀釋該濃縮物至 所需濃度。以所需濃度之活性成份調配物喷丨麗處理玉求 (厶arnfl%)葉圓片,一旦乾燥後,即在葉圓片上接種草地黏 ^XSpodoptera frugiperda)缺氣。 7天後,測定效力%。100%表示所有幼蟲死亡;〇%表 示沒有幼蟲死亡。 本試驗中’下列本發明化合物具有所示之效力: 在20 g/ha之施用率下之效力為83% : la-23; la-72;la-82 本試驗中’下列本發明化合物具有所示之效力: 在20 g/ha之施用率下之效力為1〇〇〇/。: la-54 實例7 256 201136518 猿葉蟲(Phaedon)試驗(PHAECO喷灑處理) 溶劑: 78.0份重量比丙酮 1.5份重量比二曱基甲醯胺 乳化劑:0.5份重量比烧基芳基聚二醇 製備活性成份調配物時,由1份重量比活性成份與上 述量溶劑及乳化劑混合,以含乳化劑之水稀釋該濃縮物至 所需濃度。以所需濃度之活性成份調配物喷灑處理捲心白 菜CSraaz’ca 似ζ\)葉圓片,乾燥後接種猿葉蟲(尸 cochieariae)幼备。 7天後,測定效力%。100%表示所有幼蟲死亡;0% 表示沒有幼蟲死亡。 本試驗中,下列本發明化合物具有所示之效力: 在20 g/ha之施用率下之效力為100% : la-2卜 la-22、la-23、la-37、la-4卜 la-43、la-47、la-48、 Ia_51、la-54、la-56、la-57、la-58、la-59、la-60、la-61、 la-62、la-63、la-64、la-65、la-66、la-67、la-68、la-69、 la-70、la-7卜 la-72、la-73、la-74、la-75、la-76、la-78、 la-79、la-80、la-82、la-83、la-84、Ia_86、la-87、la-88、 la-89、la-90、la-9卜 la-92、la-93、la-94、la-95、la-96、 la-97、la-98、la-99、la-100、Ia-ΗΠ、la-102、la-103、la-104、 la-105、la-106、Ia_107、la-108、la-109、la-110、la-111、 la-112、la-113、la-114、la-115、Ic-18、Ic-18、Ic-20、Ic-21、 Ic-22 、 Ic-23 、 Ic-24 257 201136518 實例8 紅葉蟎(Tetranychus)-試驗;OP-抗性(TETRUR喷灑處 理) 溶劑: 78.0份重量比丙酮 1.5份重量比二曱基曱醯胺 乳化劑:0.5份重量比烷基芳基聚二醇醚 製備活性成份調配物時,由1份重量比活性成份與上 述量溶劑及乳化劑混合’以含乳化劑之水稀釋該濃縮物至 所需濃度。 以所需濃度之活性成份調配物喷灑已感染所有階段之 溫皇 葉織(Tetranychus urticae)之 l^(Phaseolus vulgaris) 葉圓片。 6天後,測定效力%。100%表示所有紅葉蜗均死亡; 0%表示沒有紅葉蟎死亡。 本試驗中,下列本發明化合物具有所示之效力: 在20 g/ha之施用率下之效力為80% : la-63、la-77、la-90、la-92、la-94、la-95、la-96、la-99、
Ia-100、Ic-18 本試驗中,下列本發明化合物具有所示之效力: 在20 g/ha之施用率下之效力為90% : la-23、la-47、la-48、la-49、la-5 卜 Ia_57、la-58、la-60、 la-65、ia_66、la-74、la-78、la-79、Ia_93、la-115 本試驗中,下列本發明化合物具有所示之效力: 在20 g / ha之施用率下之效力為1〇〇% : 258 201136518
Ia-23、Ia_36、Ia-4卜 Ia-50、ia_52、la_54、Ia-55、Ia-56、 la 59、la-61、la-62、Ia-68、la-69、la-70、la-73、la-75、 la-112 、 la-113 、 la-114 實例9 祀蜱(Amblyomma hebaraeum)試驗(八廳¥11£) 溶劑:二甲亞砜 製備適當之活性成份調配物時,由1〇 mg活性成份與 0.5 ml二甲亞砜混合,以水稀釋該濃縮物至所需濃度。 取ί匕蜱/zehraewmj若蟲置入多孔之塑膠 杯中’ '浸入所需濃度中1分鐘。將花蜱移至培養皿之遽紙 上’保存在氣候控制室中。 42天後,測定死亡率%。100%表示所有花蜱均死亡; 〇°/〇表示沒有花蜱死亡。 本試驗中,例如:下列製備實例化合物在1〇〇 ppm之 施用率下之效力為100〇/〇 : 、Ia l62 實例10 牛蜱(Boophilus microplus)試驗(DIP) 试驗動物:成年吸血牛蜱(Boophilus microphs)維泰,sp 抗性Parkhurst品系 溶劑:二曱亞砜 取10 mg活性成份溶於0.5 ml二甲亞石風。製備人適之 調配物時,加水稀釋活性成份溶液至各所需濃度。 259 201136518 吸取此活性成份調配物至試管中。取8_1〇隻牛蜱移至 另一個有開孔之試管中。該試管浸入活性成份調配物中, 使所有牛蜱完全濕潤。待液體流完後,將牛碑移至塑膠培 養皿之渡片上’保存在氣候控制室中。7天後,由產下之 可孵化蟲卵數評估效力。將無法自外觀看出孵化力之蟲卵 保存在氣候控制室之玻璃管中,直到幼蟲孵化為止。1〇〇0/〇 之效力表示沒有牛蜱產下任何可孵化之蟲卵。 本試驗中,例如:下列製備實例化合物在1〇〇 ppm之 施用率下之效力為100% : la-112、la-162 本試驗中’例如:下列製備實例化合物在1〇〇 ppm之 施用率下之效力為98% : la-161 本試驗中,例如:下列製備實例化合物在1〇〇 ppm之 施用率下之效力為90% : la-155 本試驗中,例如:下列製備實例化合物在10〇 ppm之 施用率下之效力為85% : la-114 實例11 牛蜱(Boophilus microplus)試驗(BOOPMI 注射法) 溶劑:二曱亞砜 製備適當之活性成份調配物時,由10 mg活性成份與 0.5 ml溶劑混合,以溶劑稀釋該濃縮物至所需濃度。取活 性成份溶液注射至牛蜱腹部,將動物 移至培養皿’存放在氣候控制室中。由產下之可孵化蟲印 數評估效力。 260 201136518 7天後,測定效力%。100%表示沒有牛碑產下可畔化 之卵。 本試驗中,例如:下列製備實例化合物在2(^g/隻動 物之施用率下之效力為100% : la-5、la-8、la-18、la-19、 la-2卜 la-22、la-23、la-24、la-29、la-30、la-3 卜 la-32、 la-36、la-40、la-41、la-42、la-43、Ia-44,Ia-45、la-46、 la-54、la-57、la-58、la-60、la-73、la-75、Ia_76、la-77、 la-80、la-82、la-94、la-112、la-114、la-121、la-122、 la-123 、 la-124 、 la-125 、 la-126 、 la-127 、 la-128 、 la-129 ' la-130 > la-132 ' la-134 ' la-135 > la-136 > la-138 - la-139 ' la-140 ' la-141 ' la-142 > la-143 > la-144 > la-145 ' la-146 ' la-147 ' la-148 > la-149 ' la-150、la-151、la-152、la-153、la-154、la-155、 Ia_156 、 la-157 、 Ia_158 、 la-159 、 la-161 、 la-162 、 la-163、la-164、la-237、Ic-18、Ic-24、Ic-25 實例12 貓櫛頭蚤(Ctenocephalides felis)口服(CTECFE) 溶劑:1份重量比之二曱亞砜 製備適當之活性成份調配物時’由10 mg活性成份與 0.5 ml二曱亞砜混合。取一部份濃縮物,以經過檸檬酸鹽 處理之牛血稀釋,製備所需濃度。 取約20隻未餵食之跳蚤成蟲(貓櫛頭蚤 /e/z··?))置入上下兩面均以紗布密封之容器 261 201136518 中。取一個底部已以石堪膜(Parafilm)密封之金屬量筒置於 該容器上方。該量筒包含血液-活性成份製劑,跳蚤可透過 石蠟膜吸食。2天後,測定死亡率%。100%表示所有跳蚤死 亡;0%表示沒有跳蚤死亡。 本試驗中,例如:下列製備實例化合物在100 ppm之施 用率下之效力為100% : la-19 la-60 la-124 la-138 la-149 la-159 la-21 la-73 la-125 la-139 la-150 la-161 la-22 la-75 la-126 la-140 la-151 la-162 la-23 la-80 la-127 la-141 la-152 la-163 la-24 la-82 la-128 la-142 la-153 la-164 la-30 la-94 la-129 la-143 la-154 la-237 la-43 la-112 la-130 la-144 la-155 Ic-18 la-45 la-114 la-132 la-145 la-156 Ic-24 la-57 la-121 la-134 la-147 la-157 Ic-25 la-5 8 la-122 la-136 la-148 la-158 本試驗中,例如:下列製備實例化合物在100 ppm之 施用率下之效力為98% : la-18 本試驗中,例如:下列製備實例化合物在100 ppm之 施用率下之效力為95% : la-54 本試驗中,例如:下列製備實例化合物在100 ppm之 施用率下之效力為90% : la-146 本試驗中,例如:下列製備實例化合物在100 ppm之 施用率下之效力為80% . Ia-5、la-76 262 201136518 實例13 綠繩(Lucilia cuprina)試驗(LUCICU) 溶劑:二甲亞砜 製備適當之活性成份調配物時,由1〇 mg活性成份與 〇·5 ml二曱亞砜混合,以水稀釋該濃縮物至所需濃度。在 包含經過所需濃度之活性成份調配物處理之馬肉之容器中 妾種、勺2〇隻綠繩幼蟲。 0%表示沒有幼蟲死亡。 本試驗中’例如:下列製備實例化合物在100 ppm之 施用率下之效力為100〇/〇 : 2天後’測定死亡率%。100%表示所有幼蟲均死亡;
Ia'18 la-36 Ia~19 la-40 la-21 la-41 la-22 ia_42 la-23 ia_43 la-24 ia-45 la-25 ia>46 la-30 ia_54 Ia~32 la-57 la-60 la-124 la-141 la-153 la-237 la-75 la-125 la-143 la-154 Ic-18 la-77 la-126 la-144 la-155 Ic-24 la-82 la-127 la-145 la-156 Ic-25 la-112 la-129 la-146 la-158 la-114 la-132 la-148 la-159 la-121 la-136 la-149 la-161 la-122 la-138 la-150 la-162 la-123 la-140 la-151 la-163 本武驗中,例如:下列製備實例化合物在100 ppm之 施用率下之效力為95%:ι&·94 本試驗中’例如:下列製備實例化合物在100 ppm之 263 201136518 施用率下之效力為 90% : Ia_31、Ia-128、Ia-134、Ia-142、 la-152 本試驗中,例如:下列製備實例化合物在100 ppm之 施用率下之效力為 80% : la-29、la-73、la-80、la-139、 la-147 實例14 家*S(Musca domestica)試驗(MUSCDO) 溶劑:二曱亞砜 製備適當之活性成份調配物時,由10 mg活性成份與 0.5 ml二甲亞颯混合,以水稀釋該濃縮物至所需濃度。在 包含經過所需濃度之活性成份調配物處理之海綿之容器中 接種家繩fMwsca 成蟲。 2天後,測定死亡率%。100%表示所有家蠅均死亡; 0%表不沒有家繩死亡。 本試驗中,例如:下列製備實例化合物在100 ppm之 施用率下之效力為 1〇〇〇/0: Ia-19、Ia-23、Ia-30、Ia_45、Ia-57、 la-140、Ia_141、Ia-149、la-158、la-163、Ic-25 本試驗中,例如:下列製備實例化合物在100 ppm之 施用率下之效力為95% : la-60 本試驗中,例如:下列製備實例化合物在100 ppm之 施用率下之效力為 90% : la-18、la-122、la-142、la-148、 la-156 本試驗中,例如:下列製備實例化合物在100 ppm之 264 201136518 施用率下之效力為85°/o : Ia_4〇 本試驗中,例如:下列製備實例化合物在100 ppm之 施用率下之效力為80°/° : Ia_151、Ia_161 實例15 草地黏蟲(Spodoptera frugiperda)試驗(SPODFR 喷灑處 理) 溶劑: 78.0份重量比丙酮 1.5份重量比二曱基曱醯胺 乳化劑:0.5份重量比烷基芳基聚二醇醚 製備適當之活性成份調配物時,由1份重量比活性成 份與上述量溶劑及乳化劑混合,以含乳化劑之水稀釋該濃 縮物至所需濃度。以所需濃度之活性成份調配物喷灑處理 玉米(Z從葉圓片,乾燥後,接種草地黏蟲(处 frugiperda)缺氣。 7天後,測定效力%。表示所有幼蟲死亡;0〇/〇 表示沒有幼蟲死亡。 本試驗中,例如:下列製備實例化合物在50〇g/ha之 施用率下之效力為100% : la-3 la-71 la-90 la-104 la-123 Ic-12 Ic-41 la-8 la-72 la-91 la-107 la-229 Ic-18 Ic-42 la-10 la-73 la-92 la-108 la-231 Ic-21 Ic-44 la-11 la-74 la-93 la-109 la-233 Ic-23 Ic-45 la-17 la-75 la-95 la-110 la-236 Ic-24 265 201136518 la-21 la-78 la-96 la-111 la-237 Ic-25 la-22 la-79 la-98 la-112 la-238 Ic-31 la-23 la-80 la-99 la-113 la-240 Ic-32 la-24 la-82 la-100 la-114 la-241 Ic-34 la-44 la-85 la-101 la-116 la-246 Ic-36 la-46 la-87 la-102 la-120 la-255 Ic-37 la-68 la-89 la-103 la-122 Ic-1 Ic-39 本試驗中,例如:下列製備實例化合物在500g/ha之 施用率下之效力為 83% : la-7、la-15、la-28、la-32、 la-47 、 la-55 、 la-56 、 la-58 、 la-59 、 la-64 、 la-70 、 la-235 、 Ib-2 、 Ic-4 、 Ic-43 本試驗中,例如:下列製備實例化合物在lOOg/ha之 施用率下之效力為 100% :Ia-119、Ia-124、Ia-125、Ia-127、 la-129 la-143 la-158 la-178 la-205 la-212 la-226 la-252 la-260 la-272 la-278 la-131 la-146 la-161 la-190 la-206 la-213 la-239 la-253 la-264 la-273 la-278 la-137 la-147 la-165 la-195 la-207 la-214 la-247 la-256 la-266 la-274 la-279 la-138 la-148 la-168 la-200 la-208 la-215 la-248 la-257 la-267 la-275 la-280 la-140 la-149 la-172 la-203 la-210 la-219 la-251 la-258 la-270 la-276 la-281 la-141、 la-156 ' la-176 ' la-204、 la-211 ' la-225 ' la-251 、 la-259、 la-271、 la-277、 la-282 ' 266 201136518
Ia-282、Ia-284、Ic-26、Ic-27、Ic-29、le]、ie_2、ie_3、
If-3 本試驗中,例如:下列製備實例化合物在lOOg/ha之 施用率下之效力為 83% : la-155、la-170、ia_i75、la-179、 la-183、la-196、la-198、la-209、la-223、lf_2 實例16 猿葉蟲(Phaedon)試驗(PHAECO喷灑處理) 溶劑: 78.0份重量比丙酮 1.5份重量比二曱基甲醯胺 乳化劑:0.5份重量比烷基芳基聚二醇鱗 製備適當之活性成份調配物時,由1份重量比活性成 份與上述量溶劑及乳化劑混合’以含乳化劑之水稀釋該濃 縮物至所需濃度。以所需濃度之活性成份調配物喷灑處理 捲心白菜(价⑽⑹葉圓片,乾燥後接種猿葉蟲 (Phaedon cochleariae)幼氣。 經過所需值時間後,測定效力%。1〇〇%表示所有猿葉 蟲幼蟲均死亡;0%表示沒有猿葉蟲幼蟲死亡。 本試驗中,例如:下列製備實例化合物在500g/ha之 施用率下之效力為100% :
Ia-2 la-54 la-84 la-114 Ic-3 Ic-42 la-3 la-55 Ia_85 la-115 Ic-4 Ic-43 la-4 la-56 la-86 la-116 Ic-5 Ic-44 la-5 la-57 la-87 la-117 Ic-6 Ic-45 267 201136518
Ia-6 la-58 la-88 la-120 Ic-7 Ic-46 la-7 la-59 la-89 la-121 Ic-8 Ic-47 la-8 la-60 la-90 la-122 Ic-9 Id-1 la-9 la-61 la-91 la-123 Ic-10 Id-3 la-10 la-62 la-92 la-229 Ic-13 la-11 la-63 la-93 la-230 Ic-14 la-12 la-64 la-94 la-231 Ic-15 la-13 la-65 la-95 la-232 Ic-16 la-14 la-66 la-96 la-233 Ic-17 la-15 la-67 la-97 la-234 Ic-18 la-16 la-68 la-98 la-235 Ic-19 la-17 la-69 la-99 la-236 Ic-20 la-18 la-70 la-100 la-237 Ic-21 la-19 la-71 la-101 la-238 Ic-22 la-20 la-72 la-102 la-240 Ic-23 la-21 la-73 la-103 la-241 Ic-24 la-44 la-74 la-104 la-242 Ic-25 la-45 la-75 la-105 la-243 Ic-31 la-46 la-76 la-106 la-244 Ic-32 la-47 la-77 la-107 la-245 Ic-33 la-48 la-78 la-108 la-246 Ic-34 la-49 la-79 la-109 la-255 Ic-37 la-50 la-80 la-110 Ib-1 Ic-38 la-51 la-81 la-111 Ib-2 Ic-39 268 201136518
Ia-52 la-82 la-112 Ib-4 Ic-40 la-53 la-83 la-113 Ic-1 Ic-41 本試驗中,例如:下列製備實例化合物在500g/ha之 施用率下之效力為 83% : la-1、la-27、Ib-3、Ic-ll、Ic-2 本試驗中,例如:下列製備實例化合物在lOOg/ha之 施用率下之效力為100% : la-226 la-269 Ie-3 la-227 la-270 If-1 la-228 la-271 If-2 la-239 la-272 If-3 la-247 la-273 Ig-1 la-248 la-274 la-249 la-275 la-250 la-276 la-251 la-277 la-252 la-278 la-253 la-279 la-254 la-280 la-256 la-281 la-257 la-282 la-258 la-283 la-259 la-284 la-260 Ib-3 la-261 Ic-26 la-124 la-149 la-175 la-200 la-125 la-150 la-176 la-201 la-126 la-151 la-177 la-202 la-127 la-152 la-178 la-203 la-128 la-153 la-179 la-204 la-129 la-154 la-180 la-205 la-130 la-155 la-181 la-205 la-131 la-156 la-182 la-206 la-132 la-158 la-183 la-208 la-133 la-159 la-184 la-209 la-134 la-160 la-185 la-210 la-135 la-161 la-186 la-211 la-136 la-162 la-187 la-212 la-137 la-163 la-188 la-213 la-138 la-164 la-189 la-214 la-139 la-165 la-190 la-215 la-140 la-166 la-191 la-216 la-141 la-167 la-192 la-217 269 201136518 la-142 la-168 la-193 la-219 la-262 Ic-27 la-143 la-169 la-194 la-220 la-263 Ic-29 la-144 la-17〇 la-195 la-221 la-264 Ic-30 la-145 la-171 la-196 la-222 la-265 Ic-48 la-146 la-172 la-197 la-223 la-266 Id-4 la-147 la·173 la-198 la-224 la-267 Ie-1 la-148 la-174 la-199 la-225 la-268 Ie-2 實例Π 赤蚜(Myzus)試驗(MYZUPE喷灑處理) 溶劑: 78份重量比丙酮 1.5份重量比二甲基甲醯胺 乳化劑:〇.5份重量比烷基芳基聚二醇醚 製備適當之活性成份調配物時,由1份重量比活性成 份與上述量溶劑及乳化劑混合,以含乳化劑之水稀釋該濃 縮物至所需濃度。在受到所有階段桃赤财(Myzus persicae) 感染之捲心白菜(Brassica pekinensis)葉圓片上喷灑所需濃 度之活性成份調配物。 6天後,測定效力。/。。刚%表示所有财蟲均死亡;〇% 表示沒有蚜蟲死亡。 本試驗中,例如:下列製備實例化 施用率下之效力為l〇〇%:Ia-2l、Ia” τ物在5〇_之
Ia-59、Ia-60、Ia-64、Ia-65、Ia、7/2、Ia'23、Ia-57、Ia-58、 ' la-112 270 201136518 本試驗中,例如:下列製備實例化合物在500g/ha之 施用率下之效力為 90% : la-36、la-41、la-55、la-63、 la-67、la-69、la-78、la-79、Ic-37、Ic-44 本試驗中,例如:下列製備實例化合物在500g/ha之 施用率下之效力為 80% : la-36、la-43、la-6卜 la-62、Ic-12 本試驗中,例如:下列製備實例化合物在lOOg/ha之 施用率下之效力為 100% : la-115、la-130、la-131、la-136、 la-141 、 la-142 、 la-143 、 la-150 、 la-153 、 la-155 、 la-156 、 la-160 、 la-162 、 la-163 、 la-164 、 la-169 、 la-170 、la-174 、la-175 、la-184 、la-190 、la-195 、 la-252、la-256、la-276、la-277、la-278、la-279、 la-280、Ic-26、If-2 本試驗中,例如:下列製備實例化合物在lOOg/ha之 施用率下之效力為 90% : la-127、la-140、la-154、la-161、 Ia-179、Ia-180、la-194、la-197、la-239、la-242 ' la-282、
Ic-44 > Id-4 本試驗中,例如:下列製備實例化合物在lOOg/ha之 施用率下之效力為 80% : la-132、la-138、la-152、la-158、 la-167、Ia_168、la-187、la-251、la-254 實例18 紅葉蟎(Tetranychus)-試驗;OP-抗性(TETRUR喷灑處 理) 271 201136518 溶劑: 78.0份重量比丙酮 1.5份重量比二甲基曱醯胺 乳化劑:〇.5份重量比烷基芳基聚二醇醚 製備適當之活性成份調配物時’由1份重量比活性成 份與上述量溶劑及乳化劑混合’以含乳化劑之水稀釋該濃 縮物至所需濃度。以所需濃度之活性成份調配物喷灑已感 染所有階段之溫室紅葉蜗wri/cad之菜豆 (P/ziweo/ws 葉圓片0 6天後,測定效力%。100%表示所有紅葉蟎死亡;〇% 表示沒有紅葉蟎死亡。 本試驗中,例如:下列製備實例化合物在500g/ha之 施用率下之效力為100% : la-19 la-48 la-58 la-71 la-96 la-232 Ic-32 la-21 la-49 la-59 la-74 la-99 la-235 Ic-33 la-22 la-50 la-60 la-75 la-100 la-237 Ic-36 la-23 la-51 la-61 la-78 la-112 la-238 Ic-37 la-30 la-52 la-62 la-79 la-113 la-240 Ic-42 la-36 la-53 la-63 la-85 la-114 la-242 Ic-46 la-37 la-54 la-64 la-87 la-116 la-244 la-41 la-55 la-68 la-90 la-120 Ic-18 la-42 la-56 la-69 la-93 la-229 Ic-24 la-45 la-57 la-70 la-94 la-231 Ic-25 本試驗中 ,例如: 下列製備實例化合物在 500g/ha 之 施用率下之效力為90°/〇 : 272 201136518
Ia-18 la-43 la-80 la-91 la-97 la-104 la-111 la-236 Ic-31 la-31 la-65 la-83 la-92 la-98 la-106 la-115 la-241 la-32 la-73 la-88 la-95 la-103 la-110 la-122 la-245 本試驗中,例如:下列製備實例化合物在500g/ha之 施用率下之效力為80% : la-47 la-86 la-101 la-105 la-108 la-230 la-84 la-89 la-102 la-107 la-109 la-255 本試驗中,例如:下列製備實例化合物在lOOg/ha之 施用率下之效力為100% : la-119 la-132 la-124 la-133 la-128 la-134 la-129 la-136 la-186 la-192 la-188 la-193 la-190 la-194 la-191 la-195 la-138 la-144 la-139 la-145 la-141 la-146 la-143 la-147 la-196 la-214 la-203 la-220 la-211 la-222 la-213 la-226 la-148 la-152 la-149 la-153 la-150 la-154 la-151 la-155 la-227 la-252 la-239 la-253 la-246 la-257 la-247 la-261 la-156 la-162 la-158 la-163 la-159 la-164 la-161 la-168 la-270 la-274 la-271 la-275 la-272 la-276 la-273 la-277 la-170 la-178 la-182 la-173 la-179 la-183 la-174 la-180 la-184 la-176 la-181 la-185 la-278 la-282 If-2 la-279 Ic-29 la-280 Ic-31 la-281 Ic-45 本試驗中,例如:下列製備實例化合物在lOOg/ha之 施用率下之效力為90% : la-137 la-189 la-205 la-251 la-284 Ie-2 la-175 la-199 la-215 la-266 la-66 If-3 la-187 la-204 la-224 la-267 Ie-1 本試驗中,例如:下列製備實例化合物在lOOg/ha之 施用率下之效力為80% : 273 201136518
Ia-18 la-126 la-130 la-140 la-169 la-172 la-212 la-259 Ie-3 la-32 la-127 la-131 la-160 la-171 la-210 la-219 la-264 Ig-1 274
Claims (1)
- 201136518 七、申請專利範圍 1. 一種通式⑴化合物及其非對映異構物、對映異構物、E/z 異構物及鹽類,其中 R1為氫、函素、硝基、氰基、可視需要經單取代或經相 同或相異取代基多取代之CrC6-烷基、c2-C6-烯基、 c2-c6-炔基、CrC6-烧氧基、crC6-烧基硫基、crc6· 烧基亞確醯基、C^-CV烧基確酿基、c3_c6-環烧基、 Ci-CV烷基羰基、CrCV烷氧基亞胺基_crc6-烷基、 CrQ-烧氧基羰基、CrC6_烧基胺基羰基、crC6-二烧 基胺基羰基、CrCV烧基胺基續醯基、crc6-烷基磺醯 基胺基、三(CrC6_烷基)矽烷基、芳基、雜芳基、芳基 •CrC4-烷基,或雜芳基-CrC4-烷基, 其中該等取代基分別獨立選自:鹵素、氰基、;g肖基、 經基、CrC6-烧基、CVQ-烧氧基、c3-c6-環烧基、crc6-_烧氧基、Ci-C6_烧基硫基、C1-C6-烧基亞續釀基、 CrCV·烷基磺醯基、芳基、雜芳基、芳基烷基或雜芳 基燒基, 其中該芳基、雜芳基、芳基烷基、雜芳基烷基取代基 275 201136518 可視需要經以下取代基單取代或經以下相同或相異取 代基多取代:鹵素、氰基、硝基、羥基、cKc6-烷基、 c2-c6-稀基、c2-c6-炔基、Crc6-環烧基、Crc6_燒氧 基、CVCV齒燒基、q_c6-鹵炫氧基或基硫, 或 Rl為Cl-C4碳鏈,其可視需要包含1-2個選自N、S、0 所組成群中之雜原子,其鍵結在兩個相鄰環位置上, 且形成月曰系、芳香系、雜芳香系或雜環狀環,其可视 需要經crcv烷基或鹵素單取代或多取代,此時11為2, η 為1、2或3, R為氫、氰基、羥基、胺基、可視需要經單取代或經相 同或相異取代基多取代之Cl_C:6_烷基、c2_c6_烯基、 C2-C6-快基、Crc6-烧氧基、c3-c6-環烧基、可視需要 經早取代或經相同或相異取代基多取代之芳基、雜芳 基、或可視需要經單取代或經相同或相異取代基多取 代之芳基-CrCe-烧基或雜芳基烧基, 其中該等取代基分別獨立選自:鹵素、氰基、硝基、 羥基、胺基、q-cv烧基、(^-(v燒氧基、c3-c6-環烷 基、Ci-C6-齒烧氧基、CrC6-烧基硫基、胺基、 烧基胺基、CrCV二烧基胺基、c】-c4-炫·基羰基胺基或 CVCr二烷基羰基胺基, 或 R2為可視需要經單取代或多取代之C2-C4-烷基鏈,其中 可穿插0、S或N ’與Q1形成5-7員環,其可視需要 276 201136518 穿插o、s或N,且取代基分別獨立選自:鹵素及 烷基, 為虱了視需要經單取代或經相同或相異取代基多取 代之CpCV燒基、c2-C6·稀基、CVC6-块基、c3-C6-環 烧基、芳基-CrC6-烧基、CrC6·烧基羰基、crc6_烧基 石買醯基、芳基羰基、雜芳基羰基、C1-C6-烷氧基羰基或 芳基氧羰基, 其中該等取代基分別獨立選自:鹵素、氰基、硝基、 經基、CrC6-烧基、CrC6-烧氧基、c3-c6·環烧基、CVQ-鹵烧氧基、CrCV烧基硫基、芳基、雜芳基、芳基烧 基、雜芳基烷基、CrC4-烷氧基羰基、胺基羰基、Ci_c4_ 烧基胺基幾基或crc4-二烧基胺基幾基, 其中該芳基、雜芳基、芳基烷基、雜芳基烷基取代基 可視需要經以下取代基單取代或經以下相同或相異取 代基多取代:鹵素、.氰基、硝基、羥基、Ci_C6_烷基、 C2-CV烯基、C2-C6-炔基、c3_c6•環烧基、Ci_c6_炫氧 基、cvcv鹵炫基、crcv南烷氧基或C]_C6_燒基硫, V 為R4,或 為二價化學部份基團,其係選自:·〇_…CH2〇-、、 -N(R8)_、-N=C(R9)-、-C(R9)==n_&_c(r9)=c(riG)·,且 其利用單鍵與Q4鍵結’其中各例中之第二個(右邊)連 結位置係與Q4連結,其中 R4為氫、鹵素或可視需要經單取代或經相同或相異取代 基多取代之Crc6-烧基’其中該等取代基分別獨立選 277 201136518 自· S素、Ci-C;6-烧基或C!-C6-貌氧基, R8為氫、氰基、羥基、可視需要經單取代或經相同或相 異取代基多取代之CrCV烷基、CVQ-烯基、c2_c6_炔 基、C3-C6-環烧基、Cl_c6_烧氧基、Ci_c6烧基裁基、 芳基羰基、雜芳基羰基、CrC6_烷氧基羰基、芳基烷基 或Crc4-烷基磺醯基, 其中該等取代基分別獨立選自:齒素、氰基、硝基、 經基、CrC6_烧基或CrCV·炫氧基、Q-C4-烧氧基Μ 基、基、Ci-CV烧基胺基、(^-〇:6-二烧基胺基、胺基 羰基、CrC6_烧基胺基幾基、crc6-二烧基胺基羰基及 芳基-CrCV烷氧基, R9及R1Q分別獨立為:氫、鹵素、可視需要經單取代或經 相同或相異取代基多取代之Cj-CV烷基或c3-C6-環烷 基, 其中該等取代基分別獨立選自:鹵素及CrC6_烷基, R5為氫、鹵素或可視需要經單取代或經相同或相異取代 基多取代之CrC6-烷基或CrC6-烷氧基, 其中該等取代基分別獨立選自:鹵素及crc6-烷基, R6為氫、鹵素、硝基、氰基、胺基、羥基、可視需要經 單取代或經相同或相異取代基多取代之Crc6_烷基、 c2-c6-稀基、c2-c6-炔基、c3-c6-環燒基、crC6-炫氧 基、(CrC:6-烷氧基)羰基、crC6-烷基胺基、曱醯基、 (crc6-烧基)魏基、CrC6_烧氧基亞胺基_CrC6_炫基、 Ci-CV —炫•基胺基、(Ci-C6_烧基胺基)幾基、(Ci-C6-二 278 201136518 烷基胺基)羰基、CrC6-烷基硫基、crc6-烷基亞磺醯 基、Crc6-烷基磺醯基、C/C6-烷基胺基磺醯基、CrC6_ 烧基㉟酿基胺基、芳基、雜芳基、芳基-Ci-C4_炫基或 雜芳基-Crc4-烷基, 其中5玄專取代基分別獨立選自:鹵素、氰基、硝基、 經基、胺基、CVCV烧基、crC6·烧氧基、c3-c6-環烷 基、心<6-_烷氧基、c1<v烷基硫基、芳基、雜芳基、 芳基烷基或雜芳基烷基, 其中該芳基、雜芳基、芳基烷基、雜芳基烷基取代基 可視需要經以下取代基單取代或經以下相同或相異取 代基多取代:齒素、氰基、硝基、羥基、crc6-烷基、 C2_C6_稀基、C2-C6-炔基、c3-c6-環烧基、crC6-燒氧 基Cl 境基、Ci-C6-齒烷氧基或crc6-烷基硫基, R6 π缚 π, Λ、Mi 其可視需要包含1-2個選自N、s、Ο 環位置上,之雜原子,其鍵結在Q4至Q8中兩個相鄰 :需要婉連形成脂系、芳香系或雜芳香系環’其可 為^、’工kcv燒基或齒素單取代或多取代,此時m m Μι υ :取代或°3々鹵環烷基’其可視需要再經 基、氰基'^代,其中該等取代基分_立選自:經 氧基幾WCC4= 氧基、Ci 烷基胺基羰基及cvc^二烷基胺基羰 279 X 201136518 基, ψ為〇或S, A-Y共同為氰基’或為可視需要經單取代或多取代之雜芳 基、雜環基或酮基雜環基, 其中該等取代基選自:4素、;G肖基、氣基、胺基、經 基,選自可視需要經單取代或經相同或相異取代基多 取代之胺基、CrCV燒基、Ci-CV烧氧基、Crc6-院氧 基-Cl-C6-烧基、Ci_C6-燒基幾基、C2-C6-稀基、C2-C6-炔基、Cj-C:6-環烷基、芳基、雜芳基、Crc6-芳基烷基、 Ci-C6_雜方基烧基、方基氧、雜芳基氧、續酿基、C!-C6_ 烷基硫基、Ci-CV烷基亞磺醯基、Crc6-烷基磺醯基、 CrC6-院氧基叛基或CVCV烧基胺基裁基, 其中該等取代基分別獨立選自:齒素、硝基、氰基、 Ci-CV烧基、CrQ-齒烧基、c】-c6-烧氧基、Ci-C6-il 炫氧基、C^-Q-環烧基、Q-CV環烧基羰基、q-CV烧 基硫基、Cr(V烧基亞續酿基、crC6-燒基續醢基、 (Ci_CV烧氧基)獄基、C2-C6-浠基、C2-C6-炔基、Ci_C6_ 烷基胺基、crcv環烷基胺基、(CKCV烷基)C3-C6-環 烷基胺基或二(crc4)烷基胺基, 或 A 為二價化學部份基團,其係選自:部份基團 -NR13C(=0)- > -NR13C(=S)-' -C(R11)(R12)NR13C(=0)., -C(Rn)(U)NR13C(=0)- > -C(Ru)(R12)N(U)C(=0)- ' -C(Rn)(R,2)NR13C(=S)- 、 -C(=〇)NR13- 、 280 201136518 -C(=0)NR13CH2-、-C(=S)NR13-、-C(=S)NR13CH2-、 -C(=0)NR13C(Rn)=N-0_ 、 -C(Rn)=N-0- 、 -C(NH2)=N-0- 、 -CCR11)=N-0CH2C(=0)NR13-、 -C(Rh)(R12)NR13C(=0)NR14- 、 -c(ru)(r12)nr13c(=o)ch2s-、-nr13(c=o)nr14-、 -C(=0)- 、 -C(=N-0-R13)- 、 -C(=0)0- 、 _C(=0)0CH2C(=0)_ 、-C(=0)0CH2C(=0)NR13-、 -c(=o)nr13ch2c(=o)nr14-、-C(=0)NR13CH2C(=0)-、 -c(=o)nr13ch2c(=o)o-、-c(=o)nr13nr14c(=o)-、 -C(=0)NR13NR14-、_N(R13)-、-C(RU)(R12)NR13-、 -S(=0)p- 、 -S(=0)2NR13- 、 -NR13S(=0)2-、 -C(Rn)(R12)NR13S(=0)2-、-SO(=N-CN)-、-S(=N-CN)-、 -C(=0)NHS(=0)2-、-C(=0)N(R13)-0- , -C(=0)CH(CN)-或-CH(CN)NR13-,其中該二價化學部份基團之第一個 (左邊)連結位置係結合在環上Q4至Q8中位置之一,且 該第二個(右邊)連結位置結合在Y上,其中 U 為可視需要經取代之C2-C4-烷基,其與環上Q4至Q8 位置之A之連結位置上相鄰碳原子共同形成5-7員環, 其中該等取代基分別獨立選自:CVQj-烷基、q-Cr 烷氧基及_素,且其中 p 之數值可為0、1或2,及其中 Rn及R12分別獨立為:氫、氰基、或可視需要經單取代或 經相同或相異取代基多取代之CrC4-烷基,或C3_C6-環烷基, 281 201136518 其中該等取代基分別獨立選自:_素、氰基、硝基、 經基、CrCV烷基及CrC6-烷氣基, 或 R及R共同為C2_C5_烷基或C3_C5_烯基,其形成可視需 要包含1至兩個雙鍵之3-6員環, 或 R及R3共同為C2_C5_烷基或C;H:5_烯基,其形成可視需 要包含1至兩個雙鍵之3-7員環, 且其中 R及R分別獨立為:氫、可視需要經單取代或經相同或 相異取代基多取代之CrCV烷基或C3_C6_環烷基、 CrCV·烷基羰基、CrCV烷氧基羰基或芳基氧羰基, 其中該等取代基分別獨立選自:函素、氰基、硝基、 經基、crcv烧基或crc6-烧氧基, 或 R13及R14共同為(:2-C5-烧基或C3-C5-烯基,其形成可視需 要包含1至兩個雙鍵之3-7員環, Y 為氫、可視需要經單取代或經相同或相異取代基多取 代之Ci-Cg-烧基、C2-C6-稀基、C2-C6-炔基、C3-C6-環 烧基、CVC6-環烯基、芳基、雜芳基、雜環基或酮基雜 環基, 其中该等取代基選自:_素、;5肖基、氰基、經基,選 自可視需要經單取代或經相同或相異取代基多取代之 胺基、CrC6-炫基、c2-c6-稀基、C2-C6-块基、c3-C6- 282 201136518 環烷基、CrC6-烷基羰基、CrC6-烷氧基、CVC6-烷氧 基綠基、Ci-Cg-烧基硫基、Ci_C6_烧基亞續酿基、Ci_C6_ 烧基橫酿基、Ci-Cs-烧氧基幾基、C1-C6-烧基胺基隸 基、Ci-Cg-二烧基胺基綠基、Ci_C6_烧基胺基續酿基、 crc6-烷基磺醯基胺基、芳基、雜芳基、crc6-芳基烷 基、crc6-雜芳基烷基、芳基氧、雜芳基氧或雜環基、 CrCV烷氧基、CrC6-烷基、Ci-CV烷基羰基、磺醯基、 亞石黃蕴基、Ci_C6-院基硫基或Ci_C6_院氧基碳基, 其中該等取代基分別獨立選自:鹵素、crc6-烷基、 .經基、胺基、C!-C6-院基幾基、Ci-Cg-鹵烧基、Ci-C^ 烧氧基、Ci-C6-_炫氧基、〇3-〇6-孩·烧基、〇3-(^6-壞烧 基羰基、氰基、硝基、q-CV烷基硫基、crc6-烷基亞 石黃酿基、Ci-Cg-烧基石黃酿基、(〇ι·〇6-烧氧基)罗炭基、 稀基、C2-C6-快基、Ci-Cg-烧基胺基、C3-C6-i哀烧基胺 基、(CrC6-烷基)C3-C6-環烷基胺基、二(Ci-CO烷基胺 基或Q-C6-烷基胺基羰基, Q1至Q3分別獨立為經氫或經R1取代之碳原子,或為N, 其中該Q1至Q3中之氮原子數不超過2個, Q4 為經氫或R6取代或與V鍵結之碳原子,此時V不為 R4,或為N, Q5至Q8分別獨立為經氫、R6或A-Y取代之碳原子,或為 N,其中該Q4至Q8中之氮原子數不超過2個,其中 Q5、Q6、Q7、Q8中僅有一個經Α_γ取代。 283 201136518 2.根據申請專利範圍第1項之通式(I)化合物及其非對映異構 物、對映異構物、E/Z異構物及鹽類,其中 R 為虱、鹵素、硝基、氰基、可視需要經單取代或經相 同或相異取代基多取代之Q-CV烷基、c2-c6-稀基、 C2-C4-炔基、Q-C4·烧氧基、Ci-C4-烧基硫基、q-Q-烧基亞續酿基、C1-C4-烧基增酿基、C3-C4-環烧基、 CrC4-烷基羰基、crC4_烷氧基羰基、CrC4-烷基胺基 羰基、CrC4-二烷基胺基羰基或C〗-C4-烷基胺基磺醯 基, 其中該等取代基分別獨立選自:S素、氰基、硝基、 羥基、CVC4-烷基、CrC4-烷氧基、C3-C4-環烷基、(VC4-鹵烷氧基及CrCV烷基硫, η 為1、2或3, R2為氫、氰基、羥基、胺基、可視需要經單取代至經相 同或相異取代基三取代之CrC4·烷基、C2-C4-烯基、 c2-c4-炔基、CrC4-烷氧基或C3-C6-環烷基, 其中該等取代基分別獨立選自:鹵素、氰基、硝基、 羥基、胺基、CVC4-烷基及crc4-烷氧基, R3為氫、可視需要經單取代或經相同或相異取代基多取 代之Ci-C4-烧基、C2-C4-烯基、C2-C4-炔基、C3-C4-環 炫*基、方基-C1-C4-烧基、Ci-C4_烧基碳基、C1-C4-烧基 磺醯基、芳基羰基、雜芳基羰基、CrC4-烷氧基羰基或 芳基氧羰基, 其中該等取代基分別獨立選自:齒素、氰基、硝基、 284 201136518 羥基、CrC6-烷基、CVC6-烷氧基、c3-c6-環烷基、crc6-_烧氧基、CpC6-烧基硫基、C1-C4-烧氧基幾基、胺基 爹炭基、C1-C4-烧基胺基幾基及C1-C4-二炫基胺基幾基, V 為 R4, 或為二價化學部份基團,其係選自:-〇-、-S-、-N(R8)-、 -C(R9)=N-、-N=C(R9)-及-C(R9)=C(R1Q)-,且其利用單 鍵與Q4鍵結,其中各例分別於第二個(右邊)連結位置 與Q4連結,其中 R4為氫、鹵素或可視需要經單取代或經相同或相異取代 基多取代之crc4-烷基,其中該等取代基分別獨立選 自:齒素、CrC4-烷基及CrC4-烷氧基, R8為氫、氰基、羥基、可視需要經單取代或經相同或相 異取代基多取代之CrC4-烷基、c2-c6-烯基、CVC6-炔 基、c3-c6-環烷基、CrC4-烷氧基、Crc6-烷氧基羰基、 芳基炫•基,或CpCV烧基幾基, 其中該等取代基分別獨立選自:鹵素、氰基、硝基、 羥基、CrQ-院基、Crc6-烧氧基、CrCr烧氧基羰基、 胺基羰基、CrC4-烷基胺基羰基或CrCr二烷基胺基叛 基及芳基-CrC4-烷氧基, R9及R10為分別獨立為氫、鹵素或可視需要經單取代或經 相同或相異取代基多取代之CrCV烷基, 其中該等取代基分別獨立選自:鹵素、氰基、及CrC6-烧基, R5為氫、鹵素或可視需要經單取代或經相同或相異取代 285 201136518 基多取代之CrCr烷基,其中該等取代基分別獨立選 自:鹵素、CrQ-烷基或Cl_c4_烷氧基, R6為氫、鹵素、硝基、氰基、胺基、羥基、可視需要經 單取代或經相同或相異取代基多取代之crc4-烷基、 C2-C4-烯基、C2-C4-炔基、c3-C5-環烷基、CrC4-烷氧 基、(CrCV烷氧基)幾基、crC4-烷基胺基、曱醯基、 (CrC4-燒基)幾基、CrC4-烧氧基亞胺基-CrC4-烧基、 CVC4-二烷基胺基、(CrC4-烧基胺基)羰基、(Crc4-二 燒基胺基)羰基、CrC4-烷基硫基、crC4-烷基亞磺醯 基、CrC4_垸基磺醯基、crc4-烷基胺基磺醯基或Crc4-烷基磺醯基胺基, 其中該等取代基分別獨立選自:鹵素、氰基、硝基、 沒基、胺基、Cr(:6·烧基、Ci_c6烧氧基、c3_c6_環烧 基、CrCV鹵烷氧基及CrCV烷基硫, 或 為CrC4碳鏈,其可視需要包含1-2個選自N、S、0 ^、’且成群中之雜原子,其鍵結在Q4至Q8中兩個相鄰 環2置上,且形成脂系、芳香系或雜芳香系環,其可 ,而要經CrC6_烷基或j素單取代或多取代,此時m 為2, m 為〇、1、2、3, 1 C4齒貌基或C3_Cr®環烧基,其可視需要再經 、錄、或CrCV燒氧基單取代至三取代, 286 201136518 A-Υ係共同為氰基,或為可視需要經單取代或多取代之雜 環基或酮基雜環基,其選自下列:°比咯基、唑基、 異11号唾基、嗟π坐基、異°塞唾基、°比π坐基、味唾基、1,2,3-三唑基、1,2,4-三唑基、1,2,3-啐二唑基、1,2,4-噚二唑 基、1,3,4-呤二唑基、1,2,3-噻二唑基、1,2,4-噻二唑基、 1.3.4- °塞二α坐基、四嗤基、°比咬基、。密^定基、塔σ井基、 °比口井基、1,2,4-三σ井基、1,3,5-三σ井基、°比17各β定基、異口号 峻α定基、吼嗤α定基、4 σ坐咬基、β塞唆β定基、11 米嗤嚇·基、 咪唑啶基、1,2,4-啐二唑啶基、1,2,4-噻二唑啶基、1,2,4-三0坐°定基、1,3,4->1号二11坐11定基、1,3,4-°塞二嗤'1定基、1,3,4-三0坐β定基、各淋基、異吟唾琳基、2,3-二氫°比唾基、 3.4- 二氫°比峻基、4,5-二氫°比唾基、2,3-二氫噚嗅基、 3.4- 二氫坐基、娘咬基、酮基°比11 各咬基、3-酮基-1,2,4-三0坐°定基、5-酮基-1,2,4-三唾唆基、二酮基π比0各°定基、 酮基嗎琳基、酮基π辰咬基及酮基旅0井基, 其中該等取代基選自:鹵素、硝基、氰基、胺基、羥 基,選自可視需要經單取代或經相同或相異取代基多 取代之胺基、Ci-Cs-院基、Ci_C6-烧氧基、Ci-Cg-烧氧 基-Ci_C6-烧基、Ci_C6-烧基據基、C2-C6-炸基、C2-C6-炔基、c3-c6-環烷基、芳基、雜芳基、crc6-芳基烷基、 crc6-雜芳基烷基、芳基氧、雜芳基氧、crc6-烷基硫 基、Ci_C6_烧基亞續酿基、Ci-C6-烧基續酿基、C「C6_ 燒氧基幾基及Cl-C6-炫基胺基幾基5 其中該等取代基分別獨立選自:鹵素、硝基、氰基、 287 201136518 CrC6-烷基、Q-CV鹵烷基、Crc6-烷氧基、CrC6-鹵 烷氧基、C3-C6-環烷基、C3-C6-環烷基羰基、Ci-C6_烷 基硫基、CrC6-烷基亞磺醯基、CrC6-烷基磺醯基、 (Ci-CV炫氧基)幾基、C2-C6-稀基、C2-C6-快基、Ci-C6、 烷基胺基、c3-c6-環烷基胺基、(crc6-烷基)c3-c6-環 烷基胺基或二(crc4)烷基胺基, 或 A 為二價化學部份基團,其係選自:部份基團 -NR13C(=0)-、-NR13C(=S)-、-C(Rn)(R12)NR13C(=0)-、 -C(Ru)(U)NR13C(=0)-、-C(Rn)(R12)NR13C(=S)-、 -C(=0)NR13- 、 -C(=0)N(R13)-0- 、 -C(=0)NR13CH2-、-C(=S)NR13-、-C(=S)NR13CH2-、 -C(=0)NR13CH=N-0-、-C(Rn)=N-0-、-C(NH2)=N-0-、 -C(Rn)=N-0CH2C(=0)NR13- 、 -C(Rn)(R12)NR13C(=〇)NR14- 、 -C(RU)、 (R12)NR13C(=0)CH2S-、-NR13(C=0)NR14-、-C(哪、 -C(=N-0-R13)·、-C(=0)0-、-C(=0)0CH2C(=0)NR13-、 -C(=0)0CH2C(=0)NH-、-C(=0)NR13CH2C(=0)NR14-、 -C(=〇)NR13CH2C(=〇)-、-C(=0)NR13CH2C(=0)0-、 -C(=〇)NRI3NR14C(=〇)·、-C(=0)NR13NR14-、-N(R13)_、 -c(Rll)(R12)NR13_、-s(=0)p-、_S(=0)2NR13_、 -NR13S(=0)2- 、 -C(Rn)(R12)NR13S(=〇)2-、 -C(=〇)CH(CN)-或-CH(CN)NR13·,其中該二價化學部 份基團之第一個(左邊)連結位置係結合在環上Q4至Q8 288 201136518 結合在Y上, 中位置之一,且5玄第二個(右邊)連結位 其中 P U 可為0、1或2之數值,及其中 為可視需要經取代之c2_cv絲,其與環上q4 位置冗之連結位置上相时原子共同形成μ員環, 其中§亥專取代基分別獨立選自·南 %曰.鹵素、cvc3-烷基及 CVC3-烷氧基,及其中 或可視需要經單取代至經 crC4-燒基或C3_C6_環烷 R11及R12分別獨立為氫、氰基、 相同或相異取代基三取代之 基, 其中該等取代基分別獨立選自:齒素、氛基、石肖基、 羥基、Q-Q-烷基或crC6-烷氧基, 或 R及J112共同為C2-C5-院基或C3_C5_烯基,其形成3 6員 環,其中可視需要包含1至兩個雙鍵, 或 R 共同為C2-C5_烧基或C3_Cfr稀基,其形成3_7員 環,其中可視需要包含丨至兩個雙鍵, 及其中 R及R分別獨立為氫、可視需要經單取代或經相同或相 異取代基多取代之c】々烧基或C3_C6_環烧基、Ci_c4· 烷基羰基、CrCr烷氧基羰基或芳基氧羰基, 其中該等取代基分別獨立選自:齒素、氰基、硝基、 羥基、Ci_C4_烷基及CrC4-烷氧基, 289 201136518 或 R13及R14共同為C2_C5_烷基或C3-Q 環’其中可視需要包含1至兩個雙鍵, Y 為氫或可視需要經單取代或經相同或相異取代基多取 代之Crc6-燒基、C2-C6-稀基、C2-C6-快基、c3_c6-環 烧基、CVQ-環烯基,為可視需要經單取代或經相同或 相異取代基多取代之苯基或為可視需要經單取代或多 取代之雜環,其係選自:噻吩基、呋喃基、吡咯基、 %唑基、異嘮唑基、噻唑基、異噻唑基、吡唑基、咪 吐基、1,2,3-三唑基、1,2,4_三唑基、12,3-喝二唑基、 1,2,4_°亏二唑基、i,3,4·0?二唑基、1,2,3-噻二唑基、1,2,4-塞一坐基、1,3,4_噻二唑基、四唑基、吡啶基、嘧啶基、 二井基比畊基、1,2,4-三畊基、ι,3,5-三畊基、吼洛咬 基、異气唑啶基、吡唑啶基、嘮唑啶基、噻唑啶基、 坐咬基、1,2,4、二料基、定基、 =坐=基、基、唆基、U4· 一坐·疋基、吡咯啉基、異哼唑啉基、2,3~二氫吡唑基、 3’4 一氫比唾基、4,5_二氫。比〇坐基、二氮崎唑基、 3/^氫°?°坐基、心定基、四氫嗟吩基、㈣基、嗎琳 ς瓜馬琳基、二氫派喃基、四氮派喃基、四氮嘆吩 二’ 氧雜環己基、u_二氧雜環己基、二氧雜環 二==其四f鳴基、二祕、 撐基硫4 丁=基、氣猶雜環丁基'二氧 ^衣氧乙烷基、氮雜環丁基、氧氮雜 290 201136518 環丁基、氣氮雜環丙烷基、氧氮雜環庚基、氧氮雜環 己基、氮雜環庚基、酮基吡咯啶基、二酮基吡咯啶基、 酮基嗎琳基、酮基旅咬基、酮基底σ井基或酮基四氫°夫 喃基5 其中該等取代基選自:鹵素、硝基、氰基、羥基’選 自可視需要經單取代或經相同或相異取代基多取代之 胺基、CrC6-烧基、c「C6-烧氧基、c!-c6-烷氧基-CVC6-烷基、CKC6-烧基羰基、c2-c6-稀基、C2_C6-炔基、Crc6-壞烧基、芳基、雜芳基、Ci-Ce-芳基烧基、Q-C6-雜芳 基烷基、芳基氧、雜芳基氧、CrCV烷基硫基、CVC6· 烧基亞續酿基、Ci_C6-烧基確酿基、Cl_C6-烧氧基数基 或雜環基, 其中該等取代基可分別獨立選自:鹵素、硝基、羥基、 胺基、氰基、crc6-烷基、crc6-烷基羰基、crc6-鹵 烷基、crc6-烷氧基、crc6-_烷氧基、c3-c6-環烷基、 C3-C6-環烧基幾基、Ci-C6-烧基硫基、Ci_C6-烧基亞續 醯基、C〗-C6-烷基磺醯基、(crc6-烷氧基)羰基、c2-c6-炸基、C2-C6-块基、C1-C6-烧基胺基、C3-C6-環烧基胺 基、(crc6-烷基)c3-c6-環烷基胺基、二(crc4)烷基胺 基或crc6-烷基胺基羰基, Q1至Q3為分別獨立為經氫或經R1取代之碳原子,或為N, 其中該Q1至Q3中之氮原子數不超過2, Q4為經氫或R6取代之碳原子,或其係與V鍵結,此時V 不為R4,或為N, 291 201136518 Q5至Q8為分別獨立為經氮、R6或A-Υ取代之碳原子’或 為Ν,其中q4至q8中之氮原子數不超過2,其中Q5、 Q6、Q7、q8中僅有一個經Α-Υ取代。 3.根據申請專利範圍第1項之通式⑴化合物及其非對映異構 物、對映異構物、E/Z異構物及鹽類,其中 R1為氫、鹵素、硝基、氰基、可視需要經單取代或經相 同或相異取代基多取代之Ci-Cr烧基、C]-C4-烧氧基、 Ci-C4,燒基硫基、Ci-C/r炫基亞續醯基、CrC4-烧基績 醯基、CrCr烷基羰基、CrCV烷氧基羰基、Q-Cr烷 基胺基羰基、CrC4-二烷基胺基羰基或CrCV烷基胺基 磺醯基, 其中該等取代基分別獨立選自:齒素、氰基、硝基、 經基、C1-C4-烧基、Ci_C4_炫氧基、C3-C4-環烧基、Ci-C4_ 鹵烷氧基或crc4-烷基硫, η 為1、2或3, r2為氫、氰基、羥基、可視需要經單取代至經相同或相 異取代基三取代之CrC4-炫基或CrCr烧氧基’ 其中該等取代基分別獨立選自:函素、氰基、硝基、 羥基、胺基、CrCr炫基及CrC4-炫氧基’ R3為氫、可視需要經單取代或經相同或相異取代基多取 代之C1-C4-烧基、C2-C4-稀基、C2-C4-快基、C1-C4-炫 基羰基、CrC4-烷基磺醯基、ci-c4-烷氧基羰基或芳基 氧羰基, 292 201136518 其中該等取代基分別獨立選自:_素、氰基、硝基、 羥基、CrC6-烧基、CrCV炫氧基或Q-CU-烧氧基羰基, V 為R4,或為二價化學部份基團’其係選自:_〇_、 及-N(R8)-,且利用單鍵與Q4鍵結,其中 R4為氫或可視需要經單取代至經相同或相異取代基三取 代之CrC4-坑基,其中該等取代基分別獨立選自:齒 素、CrC4-烷基及Q-C4-烷氧基, R 為鼠、氰基、經基、可視需要經單取代或經相同或相 異取代基多取代之CrCr烷基、C2-C4-烯基、C3-C4-炔 基、芳基-Ci-Q-烷基、CVQ-烷氧基、Crc6_烷氧基羰 基或G-cv院基幾基, 其中該等取代基分別獨立選自:齒素、氰基、硝基、 羥基、CrC6-烷基、CrC6-烧氧基、CVC4-烷氧基羰基、 胺基1¾•基、C1-C4-炫》基胺基k基、C1-C4··二烧基胺基罗炭 基或芳基-crc4-烷氧基, R5為氫,或可視需要經單取代至經相同或相異取代基三 取代之crc4··烷基,其中該等取代基分別獨立選自: 鹵素、crc4-烷基或crc4-烷氧基, R6為氫、鹵素、硝基、氰基、可視需要經單取代或經相 同或相異取代基多取代之Crc4_烷基、C2-C4_炔基、 CrCr烷氧基、(CrC4-烷基)羰基、(CrC4-烷基胺基) 羰基、(CrC4-二烷基胺基)羰基、CrC4-烷基硫基、 CrC4-烷基亞磺醯基、CrC4-烷基磺醯基、CrCp烷基 胺基磺醯基或Q-Cr烷基磺醯基胺基, 293 201136518 其中該等取代基分獅立選自:_素、氰基、硝,基、 Q-Q-烧基、CrCV燒氧基、CrC6碥炫氧基及Ci_C6_ 烷基硫, 或 R6 為-0CH20-、-0CF20_、_〇CH2CH2〇_、-OCF2CF2〇 或 -CH=CH-CH=CH-,其中各取代基利用兩個選自〇4至 Q8中之相鄰基團形成環, m 為0、1、2、3, X為CrCVii烷基或GVCVii環烷基,其可視需要再經 羥基、氰基、或CVC4-烷氧基單取代至三取代, W 為0, A-Y為共同為乱基、或為可視需要經單取代或多取代之選 自下列之雜ί哀基:°比σ各基、崎β圭基、異4 α坐基、β塞唾 基、異嗟唾基、°比嗤基、咪唑基、2-咪哇琳基、ι,2,3-三唑基、1,2,4-三唑基、ι,2,3-崎二唑基、1,2,4-呤二唑 基、1,3,4-嘮二唑基、ι,2,3-噻二唑基、1,2,4-噻二唑基、 1,3,4-°塞二<»坐基、四《»坐基、η比咬基、。密α定基、塔U井基、 吼畊基、1,2,4-三畊基及1,3,5-三畊基’ 其中該等取代基選自:齒素、硝基、氰基、羥基,選 自可視需要經單取代或經相同或相異取代基多取代之 胺基、CrCr烧基、CrC4-炫·氧基、C1-C4-烧氧基-CrC4-烧基、C2_C4-块基、C1-C6-烧基硫基、Cl-Cg-烧基亞㈣ 醯基、CrCV烷基磺醯基、c3-c6-環烷基、芳基及雜芳 基, 294 201136518 其中該等取代基分別獨立選自:鹵素、羥基、胺基、 硝基、氰基、CrC6-燒基、crc6__烧基、Cl_c6-烧氧 基、CrC6-鹵烧氧基、C3-C6-環烧基、c3-c6-環烧基幾 基、C「C6-烧基硫基、CVC6·烧基亞磺醯基、c「c6-烧 基磺醯基、(CrC6_院氧基)幾基、c2_c6_烯基、c2-C6-块基、CrC6-烧基胺基、c3-c6-環烧基胺基、(crc6-烷基)Cs-C:6-環烷基胺基、二(Ci_c4)烷基胺基或Crc6-烧基胺基艘基, A 為二價化學部份基團,其係選自:部份基 ®-NR13C(=0)- ' -C(Rn)(R12)NR13C(=0)- ' -C(=0)0- > -C(Rn)(U)NR13C(=0)-、-c(Rn)(R12)N(U)C(=0)-、 -C(=0)NR13-、-C(=〇)N(R13)-〇-、_c(=〇)NR13CH2-、 -C(=0)NR13CH=N-0- 、 -C(Rn)=N-0- 、 -C(Rn)=N-0CH2C(=0)NR13- 、 -C(Rn)(R12)NR13C(=0)NR14- 、 -C(Rn)(R12)NR13C(=〇)CH2S·、-NR13(C=0)NR14-、 -C(=0)-、-C(=N-0-R13)-、-C(=0)NR】3CH2C(=0)NR14-、 -C(=0)NR13CH2C(=0)_、-C(=0)NR13CH2C(=0)0-、 -C(=0)NR13NR14C(=0)-、-C(=〇)NR13NR14-、-N(R13)-、 -C(Rn)(R12)NR13·、-S(=〇)p-、_S(=0)2NRl3_、 -NR13S(=0)2- 、 -C(Ru)(R12)NR13S(=〇)2-、 C(=0)CH(CN)-或-CH(CN)NR13-,其中該二價化學部份 基團之第一個(左邊)連結位置係結合在環上Q4至Q8 中位置之一,且該第二個(右邊)連結位置結合在γ上, 295 201136518 其中 p u 可為〇、1或2之數值;及其中 成基,其與環上(34至Q* 其中該等取=八職1目_原子制形成5·6員環, 其^該專取代基刀別獨立選自:CKV烧基及幽素,且 R11及R12分別獨立為氫、c 戋 1匕4烷基或cvc4-齒烷基, R11及R】2共同為CrC烷基岑 朴丄、 兀丞及C3_C5-烯基,其形成3-0員 辰,八中可視需要包含1至兩個雙鍵, 或 R及:3共同為c2-c5-烷基或c3々烯基,其形成3 7員 壤,其中可視需要包含1至兩個雙鍵, 及其中 R13及R14為分別獨立為氫 '可視需要經單取代或經相同或 相異取代基多取代之Cr(:4_^或C3_C6環燒基、 CrCV烷基羰基、芳基氧羰基或Ci_c4_烷氧基羰基, 其中該等取代基分別獨立選自:鹵素、氰基、Ci_C4_ 燒基及C〗-C4-烷氧基, 或 R13及^R14共同為C2_C5_烷基或C3_C5_烯基,其形成3_7員 衣其中可視需要包含1至兩個雙鍵, Y為氫或可視需要經單取代或經相同或相異取代基多取 代之crc6-烧基、c2-c6-嫦基、c2-c6-炔基、c3-c6-環 296 201136518 院基、cvcv環烯基’為可視需要經單取代或經相同或 相異取代基多取代之苯基或為可要單取代或多取 代之雜環’其係選自:料基、π夫喃A、^各基、4 嗤基、異十坐基、嘆唾基、異嗔唾基^坐基、# 基1,2,3-一唑基、1,2,4_三唑基、is,〕·崎二唑基、 1,2:4-4二哇基、1,3,4巧二唆基、⑴丄塞二吐基、以々 坐基1,3,4塞—唾基、四唾基“比咬基“密咬基、 ”基、U,4""三。井基、U,5-三口井基、略口井基、 ,木基、四虱派喃基、认二氣雜環己基、二氧雜 己基厂氧雜%戊基、二氣雜環戊烯基、四氫吱喃 基、二虱外基、氧雜環丁基、硫雜環丁基、氧樓基 硫雜環丁基、二氧撐基硫雜環丁基、環氧乙炫基、乳 雜環丁基、氧氮雜環丁基、氧氮雜環庚基、氧氣雜環 己基、氮雜環庚基、_基^各„定基、二酮基^比略咬基、 嗣基嗎淋基、酮基旅啶基、蜩基哌畊基及酮基四氫呋 喃基’ 其中該等取代基選自:_素、硝基、氰基、羥基,選 自可視需要經單取代或經相同或相異取代基多取代之 胺基、CrCV烧基、CVCV燒氧基、Ci_c6_烧氧基_Crc6-烧基、Crc6-院基Μ基、c2<v烯基、C2-C6-炔基、crc6· 環烷基、芳基、雜芳基、C/C6-芳基烷基、CVCV雜芳 基烷基、芳基氧、雜芳基氧、匕^^烷基亞磺醯基、 CrCV烷基磺醯基、CVCV烷基硫基、CrC6-烷氧基羰 基及雜環基, 297 201136518 其中該等取代基可分別獨立選自:鹵素、硝基、羥基、 胺基、氰基、Ci-CV烧基、CVC6-烧基幾基、CrQ-齒 燒基、crc6-烷氧基、crc6-鹵烷氧基、c3-c6-環烷基、 q-C6-環烷基羰基、crc6-烷基硫基、CrC6-烷基亞磺 酿基、CrC6-烧基續酿基、(Ci-CV烧氧基德基、c2-c6-歸基C2-C6-快基、C1-C6-院基胺基、C3-C6-環烧基胺 基、(CrCV烧基)CVCV環烧基胺基、二(crc4)烧基胺 i基及cvc6-烷基胺基羰基, Q至Q3為分別獨立為經氫或經Ri取代之碳原子,或為N, 4其中Q1至Q3中之氮原子數不超過1, Q為經氫或R6取代之碳原子,或其係與V鍵結,此時v 不為R4,或為N, Q至Q8為分別獨立為經氫、R6或Α_γ取代之碳原子,戋 為N,其中該Q4至Q8中之氮原子數不超過!,其中 Q5、Q6、Q7、Q8中僅有一個經A-Y取代。 4.根據申請專利範圍第1項之通式⑴化合物及其非辦映異構 物、對映異構物、E/z異構物及鹽類,其中 、八 Rl為氫、硝基、氰基、氟、氣、溴、碘、曱基、乙基、 正·或異丙基、氟曱基、氣曱基、三氣曱基、二氟甲1、 二氯氟曱基、氣二氟曱基、三氟曱基、氟乙基、氣乙 基、二氟乙基、二氣乙基、三氟乙基、氣氟乙基、氯 二氟乙基、二氣氟乙基、四氟乙基、五氟乙基、氯四 氟乙基、二氣乙基、七氣-正丙基、七氣異丙基、甲氧 298 201136518 基、乙氧基、正-或異丙氧基、II曱氧基、二氟曱氧基、 三氟曱氧基、曱基硫、乙基硫、二氟曱基硫、三氟甲 基硫、氯二氟曱基硫、曱基亞磺醯基、三氟甲基亞磺 醯基、三氟甲基磺醯基、甲基磺醯基、乙基磺醯基、 乙醯基、丙醯基、曱氧基羰基、乙氧基羰基、甲基胺 基叛基、二曱基胺基幾·基或乙基胺基幾基’ η 為1、2或3, R2 為氫、曱基或乙基, R3 為氫、曱基、乙基、2-乙炔基、2-丙烯基、曱氧基甲 基、乙氧基曱基、曱基羰基、乙基羰基、曱氧基羰基、 乙氧基羰基、正丙氧基羰基、異丙氧基羰基、正丁氧 基羰基、第三丁氧基羰基或苯氧基羰基, V 為R4,或為-0-或-N(R8)-,且係利用單鍵與Q4鍵結, 及其中 R4 為氫或曱基,及 R8為氫、曱基、乙基、甲基羰基、乙基羰基、曱氧基曱 基、乙氧基甲基、氰基甲基、氰基乙-2-基、丙基、苯 基甲基、丙-2-細-1 -基、丙-2-快-1 -基、苯曱基氧、曱 氧基幾基、乙氧基幾基、曱氧基魏基曱基、乙氧基幾 基曱基、曱氧基羰基乙-2-基、乙氧基羰基乙-2-基、醯 胺基曱基、醯胺基乙基或醯胺基丙-3-基, R5為氫, R6為氫、石肖基、氰基、氟、氯、>臭、蛾、曱基、乙基、 正-或異丙基、正-、異-、第二-或第三-丁基、乙炔基、 299 201136518 丙炔基、氟曱基、氣曱基、三氣曱基、二氟曱基、二 氯氟曱基、氯二氟曱基、三氟曱基、氟乙基、氯乙基、 二氣乙基、二氯乙基、三氟i乙基、氯氣乙基、氯二氟1 乙基、鼠二氯乙基、四鼠乙基、五氣乙基、氮四氣乙 基、三氯乙基、七IL -正丙基、七氟i異丙基、曱氧基、 乙氧基、正-或異丙氧基、氟曱氧基、二氟曱氧基、三 氟曱氧基、曱基硫、乙基硫、二氟曱基硫、三氟甲基 硫、氣二氟曱基硫、曱基亞磺醯基、三氟曱基亞磺醢 基、三氟甲基磺醯基、曱基磺醯基、乙基磺醯基、乙 醯基、丙醯基、甲氧基羰基、乙氧基羰基、曱基胺基 幾基、乙基胺基幾基或二甲基胺基幾基* m 為0、1或2, X 為三氟曱基、二氟曱基、氟曱基、氯二氟曱基、二氣 氟甲基、2-氟乙基、2,2-二氟乙基、2,2,2-三氟乙基、 1,2,2,2-四氟乙基、1-氣-1,2,2,2-四氟乙基、2-氯-2,2-二 氟乙基、1,1-二氟乙基、五氟乙基、七氟正丙基或九 氟》-正丁基^ W 為0, A-Y為共同為氰基,或為可視需要經單取代或多取代之選 自下列之雜環基:1,2,4-畤二唑-3-基、1H-咪唑-1-基、 1H-吡唑-1-基、1H-1,2,4-三唑-1-基、1H-1,2,3-三唑-1-基、1H-1,3,4-三唑-1-基、1H-1,2,3,4-四唑-1-基或 2H-1,2,3,4-四唑-1-基, 其中該等取代基選自:氟、氯、氰基、羥基、胺基、 300 201136518 甲基、乙基、二氟曱基、三氟i曱基、五氟乙基、正-或 異丙基、環丙基、曱氧基、乙氧基、正-或異丙氧基、 氟曱氧基、二氟甲氧基、三氟甲氧基、氟乙氧基、二 氟乙氧基、三氟乙氧基、曱基硫、曱基亞磺醯基、甲 基磺醯基、乙基硫、乙基亞磺醯基、乙基磺醯基、甲 氧基羰基、乙氧基羰基、甲基胺基羰基或二曱基胺基 幾基, 或 A 為二價化學部份基團,其係選自:部份基團-NR13C(=0)-、 -C(Rh)(R12)NR13C(=0)- 、 -C(Rh)(R12)NR13S(=0)2- ' -C(=0)NR13- ' -C(=0)N(R13)-0- 、-c(=o)nr13ch2_、-s(=o)p---S(=0)2NR13-、-c(=o)o-、 -C(=0)NR13CH2C(=0)NR14- 、 -C(Rn)(R12)NR13- 、 c(ru)(u)nr13c(=o)-、及-c(=o)nr13nr14-,其中該二價化 學部份基團之第一個(左邊)連結位置係結合在環上Q4至Q8 中位置之一,且該第二個(右邊)連結位置結合在Y上,其 中 U 為乙基或正丙基,其與環上Q4至Q8位置之A之連結 位置上相鄰碳原子共同形成5或6員環, p 為0、1、2,及其中 R11及R12分別為氫或曱基, R13及R14分別為氫、甲基、乙基、環丙基、氰基乙基、2-乙炔基、2-丙烯基、曱氧基曱基、乙氧基曱基、曱基 羰基、乙基羰基、正丙基羰基、異丙基羰基、正丁基 301 201136518 丁絲基、甲氧顧基、乙氧基幾基、正 3基異丙氧舰、正丁氧基祕、第三丁 氣基斂基或本氧基羰基, γ ^或可視需要經單取代或經相同或相異取代基多取 代之甲基、乙基、正-或異丙基、正…異_、第二-或第 三-丁基、正-、異“第二-、第三或新-戊基、環丙基、 壤丁基、環戊基、環己基、乙烯基、丙烯基、丁稀基、 戊烯基、乙炔基、丙炔基、丁炔基或戊炔基, 其中至多5個取代基可選自:氟與氣,及至多2個取 代基可選自:溴、氰基、硝基、經基、胺基、曱基胺 基、二曱基胺基、環丙基、三氟甲基、甲氧基、乙氧 基、正-或異丙氧基、氟甲氧基、二氟f氧基、三氟甲 氧基、敗乙氧基、一氟乙氧基、三乙氧基、曱基硫、 甲基亞磺醯基、甲基磺醯基、乙基硫、乙基亞磺醯基、 乙基磺醯基、甲氧基羰基及乙氧基羰基, 且其中一個取代基可選自:可視需要經單取代至三取 代之苯基、》比。定-2-基、比定_3-基、°比咬-4-基、°塞唾-2-基、β塞唾-4_基、吱喃-2-基、〇比τι坐-1-基、n比嗤_5_基及 吡唑-3-基,其中該等取代基可選自:氟、氣、溴、氰 基、硝基、羥基、曱基、乙基、正-或異丙基、胺基、 甲基胺基、二曱基胺基、環丙基、曱氧基、乙氧基、 正-或異丙氧基、氟曱氧基、二氟曱氧基、三氟甲氧基、 氟乙氧基、二氟乙氧基、三氟乙氧基、甲基硫、甲基 亞續酿基、曱基續酿基、乙基硫、乙基亞橫酿基或乙 302 201136518 基石夤酿基, 或 材視^料取代至三取代之氧純丁 雜 占衣 '四虱南-2·基、四氫咬鳴-3-基、四氫派 喃-2-基、四氣旅喃-3-1、m > 四氣哌喃-4-基、1,3-二氧雜 :己;2:基:1,3-二氧雜環己I基、U-二氧雜環己-4- 基、嗎琳小基、苯基、龄2_ 基、11比咬-3-基、吼唆_4 A a 疋4基、嘧啶_2_基、嘧啶-4-基、 ^定-5-基、外3-基、叫2_基、咬喃_2•基、吱喃-3· 基"塞吩·2·基、輕士基、料_2·基寺坐_2-基、 ,坐4基,唑_5_基、l2,4-噻二唑-5-基、》咢唑-2-基、 ^-4-基H5_基、異啊_3_基、異十坐_4_基、異 ^-5-基、U’3-H4$、…永#基、m_ =坐-2-基、1H-咪唾-4-基、瓜味唾」基、1Η_π比嗤-3_ ς 1H-比。坐·4-基、ijjh5 基、ih i 2 4 三嗤_3_ =1Η-1,2,4·二唾-5·基、1H],2,3 三唾_4_基、出心以 二唾-5-基—、2Η·1,2,3·三唾_2_基、2H1,2,3•三吐·4 基、 1,3,4 一坐2-基、如1,2,3,4-四唑-5-基、2-酮基略 ,基、2,基四氫呋喃·3_基或5-酮基四氫呋喃-2-基, 氯、溴、氰基、硝基、羥 其中該取代基可選自:氣 Ϊα胺ί、二基、乙基、二氟甲基、三氟曱基、五氟 土 或/、丙基、環丙基、曱氧基、乙氧基、 303 201136518 或異丙氧基、氟甲氧基、二氟甲氧基、三說曱氧基、 氟乙氧基、一氟乙氧基、三氟J乙氧基、曱基硫、甲基 亞磺醯基、曱基磺醯基、乙基硫、乙基亞磺醢基、乙 基續酿基、甲氧基裁基、乙氧基緩基、曱基胺基幾武 及二甲基胺基羰基, & Q〗至Q3分別獨立為經氫或經R1取代之碳原子,或為N, 其中Q1至Q3中之氮原子數不超過1, Q4為經氫或R6取代之碳原子,或其係與V鍵結,此時v 不為R4, Q5至Q8分別獨立為經氫、R6或A-Y取代之碳原子,或為 N,其中Q5至Q8中之氮原子數不超過1,且其中q5、 Q6、Q7、Q8中僅有一個經A-Y取代。 5.根據申請專利範圍第4項之通式(I)化合物及其非對映異構 物、對映異構物、E/Z異構物及鹽類,其中V為R4,且汉4 為氫’此外其中R5為氫,此外其中W為〇。 6· 一種製備根據申請專利範圍第1項之通式(I)化合物之方 法,其中 a)由通式(III)胺類304 201136518 與通式(π)羧酸或羰基ii化物反應,其中L為鹵素或羥基,及其中Q1至Q1 2、R1至R6、A、X、 Y、V、m及η分別如根據申請專利範圍第1至4項中任一 項之定義, 得到通式(I)化合物,其中W為0,及 b)可視需要由式(I)中W為Ο之化合物繼續與硫磺酸化劑反 應,得到通式(I)化合物,其中W為S。 RΗ 〆 3 NIR 與式(V)丙烯酸衍生物反應 305 (V) 1 一種製備根據申請專利範圍第5項之式(I)化合物之方法, 其中 2 a)由通式(III)胺類 201136518 得到通式(νι)丙烯醯胺類及 b)由通式(VI)丙烯醯胺類繼續與通式(VII)鹵素化合物於鈀 觸媒之存在下反應,得到通式(I)化合物,其中L為鹵素或羥基,及其中L1為 氯、溴、碘或三氟曱磺酸根,及其中Q1至Q8、R1至R6、 A、X、Y、m及η分別如申請專利範圍第5項之定義。 8. 一種通式(VI)化合物,其中Q1至Q3、R1、R2、R3、X及η分別如申請專利範圍第 4項之定義,但不包括其中Q1至Q3分別為-CH及R1、R2、 306 201136518 R3分別為Η及η為1之化合物。 9. 一種製備殺蟲劑之方法,其中由根據申請專利範圍第1項 之通式(I)化合物與/或其鹽類與增量劑與/或界面活性劑混 合。 10. —種申請專利範圍第1項之通式⑴化合物與/或其鹽類於製 造殺蟲劑上之用途。 11. 一種殺蟲劑,其包含根據申請專利範圍第1項之通式(I)化 合物與/或其鹽類,其含量為占殺蟲劑重量之〇.〇〇〇〇〇〇01至 至高95重量%之生物活性量。 12. 根據申請專利範圍第11項之殺蟲劑,其包含其他農化活性 成份。 13. —種控制動物害蟲之方法,其係使根據申請專利範圍第1 項之通式(I)化合物與/或其鹽類作用在動物害蟲與/或其棲 息地上。 307 201136518in which R1 to R6, Q1 to Q8, A, V, W, X, Y, n and m are each defined as described in the description - and to a process for preparation thereof and to the use thereof as insecticides and acaricides. 四、 指定代表圖: (一) 本案指定代表圖為:無 (二) 本代表圖之元件符號簡單說明:無 五、 本案若有化學式時,請揭示最能顯示發明特徵的化學式: 盔 2專利申請案第99136408號 ROC Patent Appln. No. 99136408 正後無劃線之中文說明書替換頁一附件(一) Amended Claims in Chinese — Encl/fi (民國100年5月20曰送呈) (Submitted on May 20,2011) 201136518 纖維素或聚合物製成之蒸發片之蒸發器產品、液體蒸發 器、凝膠及膜式蒸發器、螺漿驅動式蒸發器、無能源或被 動式蒸發系統、捕蟲紙、捕蟲袋及捕蟲膠,呈粒狀或細粉, 用於撒播式誘餌或用於誘餌台等形式使用。 【實施方式】 製法及中間物之說明 本發明亦有關一種製備通式(I)化合物之方法Ο (I) 其中()1至(^8、111至116、入、\、丫、¥、111及11分別 如上述定義, 其中 a)由通式(III)胺類 οΗ \ 3 NIR 與通式(II)羧酸或羰基齒化物反應,95 (II) 201136518 其中L為鹵素或羥基, 得到通式⑴化合物,其中W為0(氧原子),及 b)可視需要由通式(I)化合物,其中W為0(氧原子)隨後再 與硫磺酸化劑反應,得到通式(I)化合物,其中W為S(硫原 子)。 本發明亦有關通式(I)中V為R4, R4為氫之化合物,及 其中R5為氫之化合物,及其中W為0之化合物。此等化 合物相當於下示化學式反應流程3中之通式(1-3)化合物。 本發明亦有關另一種製備本發明通式(1-3)化合物之較 佳製法,其示於化學式反應流程3,其中 a)由通式(III)胺類與通式(V)丙烯酸衍生物反應,得到通式(VI)丙烯醯胺類, 96
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WO2011054436A3 (de) | 2011-07-07 |
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IL231407A (en) | 2014-11-30 |
IL218986A0 (en) | 2012-06-28 |
CN102741222B (zh) | 2015-12-02 |
CO6531496A2 (es) | 2012-09-28 |
BR112012010042A2 (pt) | 2015-09-29 |
IL218986A (en) | 2016-12-29 |
CN102741222A (zh) | 2012-10-17 |
AR078641A1 (es) | 2011-11-23 |
IL231407A0 (en) | 2014-04-30 |
EP2493844A2 (de) | 2012-09-05 |
US20130172390A1 (en) | 2013-07-04 |
WO2011054436A2 (de) | 2011-05-12 |
US8710242B2 (en) | 2014-04-29 |
WO2011054436A8 (de) | 2012-02-16 |
KR20120102617A (ko) | 2012-09-18 |
MX2012004886A (es) | 2012-05-23 |
UY32940A (es) | 2011-05-31 |
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