JP2005513137A - ４”位にアミノスルホニルオキシ置換基を有するアベルメクチン誘導体 - Google Patents
４”位にアミノスルホニルオキシ置換基を有するアベルメクチン誘導体 Download PDFInfo
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- JP2005513137A JP2005513137A JP2003554704A JP2003554704A JP2005513137A JP 2005513137 A JP2005513137 A JP 2005513137A JP 2003554704 A JP2003554704 A JP 2003554704A JP 2003554704 A JP2003554704 A JP 2003554704A JP 2005513137 A JP2005513137 A JP 2005513137A
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- Prior art keywords
- alkyl
- alkoxy
- substituted
- phenyl
- formula
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- -1 aminosulfonyloxy substituent Chemical group 0.000 title claims description 90
- RRZXIRBKKLTSOM-XPNPUAGNSA-N avermectin B1a Chemical class C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 RRZXIRBKKLTSOM-XPNPUAGNSA-N 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 118
- 239000000203 mixture Substances 0.000 claims abstract description 80
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 79
- 239000004480 active ingredient Substances 0.000 claims abstract description 42
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 29
- 150000002367 halogens Chemical class 0.000 claims abstract description 29
- 238000000034 method Methods 0.000 claims abstract description 27
- 238000002360 preparation method Methods 0.000 claims abstract description 22
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 17
- 125000001424 substituent group Chemical group 0.000 claims abstract description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 11
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims abstract description 9
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 8
- 230000000749 insecticidal effect Effects 0.000 claims abstract description 8
- 125000004450 alkenylene group Chemical group 0.000 claims abstract description 7
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
- 125000001475 halogen functional group Chemical group 0.000 claims abstract 2
- 241000607479 Yersinia pestis Species 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 239000002671 adjuvant Substances 0.000 claims description 11
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 10
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000004104 aryloxy group Chemical group 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 10
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000004643 (C1-C12) haloalkoxy group Chemical group 0.000 claims description 8
- 125000004641 (C1-C12) haloalkyl group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 6
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 238000006467 substitution reaction Methods 0.000 claims description 5
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
- 125000005149 cycloalkylsulfinyl group Chemical group 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
- 238000000227 grinding Methods 0.000 claims description 3
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 2
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 2
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims description 2
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 2
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims description 2
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 2
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 2
- XTKDAFGWCDAMPY-UHFFFAOYSA-N azaperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCN(C=2N=CC=CC=2)CC1 XTKDAFGWCDAMPY-UHFFFAOYSA-N 0.000 claims 1
- 239000007858 starting material Substances 0.000 abstract description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 40
- 239000000243 solution Substances 0.000 description 35
- 241000196324 Embryophyta Species 0.000 description 33
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
- 239000000047 product Substances 0.000 description 20
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 229910052794 bromium Inorganic materials 0.000 description 15
- 230000000694 effects Effects 0.000 description 15
- 239000011734 sodium Substances 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- 238000001704 evaporation Methods 0.000 description 14
- 230000008020 evaporation Effects 0.000 description 14
- 229910052938 sodium sulfate Inorganic materials 0.000 description 14
- 235000011152 sodium sulphate Nutrition 0.000 description 14
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 13
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 13
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000000460 chlorine Substances 0.000 description 12
- 229910052801 chlorine Inorganic materials 0.000 description 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 12
- 241001465754 Metazoa Species 0.000 description 11
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 239000000839 emulsion Substances 0.000 description 11
- 239000000741 silica gel Substances 0.000 description 11
- 229910002027 silica gel Inorganic materials 0.000 description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 10
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 229910052731 fluorine Inorganic materials 0.000 description 10
- 239000011737 fluorine Substances 0.000 description 10
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000002202 Polyethylene glycol Substances 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
- 239000000654 additive Substances 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- 229920001223 polyethylene glycol Polymers 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 8
- 240000001307 Myosotis scorpioides Species 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 230000009471 action Effects 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- 230000007423 decrease Effects 0.000 description 7
- 239000008187 granular material Substances 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 238000005507 spraying Methods 0.000 description 7
- 239000004094 surface-active agent Substances 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 125000006239 protecting group Chemical group 0.000 description 6
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- 241000238631 Hexapoda Species 0.000 description 5
- 241000244206 Nematoda Species 0.000 description 5
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- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
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- 239000012300 argon atmosphere Substances 0.000 description 4
- RRZXIRBKKLTSOM-UHFFFAOYSA-N avermectin B1a Natural products C1=CC(C)C(C(C)CC)OC11OC(CC=C(C)C(OC2OC(C)C(OC3OC(C)C(O)C(OC)C3)C(OC)C2)C(C)C=CC=C2C3(C(C(=O)O4)C=C(C)C(O)C3OC2)O)CC4C1 RRZXIRBKKLTSOM-UHFFFAOYSA-N 0.000 description 4
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000001188 haloalkyl group Chemical group 0.000 description 4
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- 239000011630 iodine Substances 0.000 description 4
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- 229940098779 methanesulfonic acid Drugs 0.000 description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 4
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- QAHVHSLSRLSVGS-UHFFFAOYSA-N sulfamoyl chloride Chemical compound NS(Cl)(=O)=O QAHVHSLSRLSVGS-UHFFFAOYSA-N 0.000 description 4
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- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
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- 150000001408 amides Chemical class 0.000 description 3
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- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 3
- ZFUKERYTFURFGA-PVVXTEPVSA-N avermectin B1b Chemical class O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O3)C=C[C@H](C)[C@@H](C(C)C)O4)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C ZFUKERYTFURFGA-PVVXTEPVSA-N 0.000 description 3
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- 125000006000 trichloroethyl group Chemical group 0.000 description 1
- 229960002415 trichloroethylene Drugs 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/22—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains four or more hetero rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/01—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing oxygen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH23632001 | 2001-12-21 | ||
| CH11902002 | 2002-07-05 | ||
| PCT/EP2002/014671 WO2003053988A2 (en) | 2001-12-21 | 2002-12-20 | Avermectin b1 derivatives having an aminosulfonyloxy substituent in the 4''-position |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005513137A true JP2005513137A (ja) | 2005-05-12 |
| JP2005513137A5 JP2005513137A5 (enExample) | 2006-02-16 |
Family
ID=25738950
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003554704A Pending JP2005513137A (ja) | 2001-12-21 | 2002-12-20 | ４”位にアミノスルホニルオキシ置換基を有するアベルメクチン誘導体 |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US6933260B2 (enExample) |
| EP (1) | EP1456218B1 (enExample) |
| JP (1) | JP2005513137A (enExample) |
| KR (1) | KR20040068335A (enExample) |
| CN (1) | CN1608075A (enExample) |
| AR (1) | AR037938A1 (enExample) |
| AT (1) | ATE397007T1 (enExample) |
| AU (1) | AU2002361197A1 (enExample) |
| BR (1) | BR0215170A (enExample) |
| CA (1) | CA2469905A1 (enExample) |
| CO (1) | CO5590963A2 (enExample) |
| CY (1) | CY1108269T1 (enExample) |
| DE (1) | DE60226895D1 (enExample) |
| DK (1) | DK1456218T3 (enExample) |
| ES (1) | ES2307823T3 (enExample) |
| HU (1) | HUP0402290A2 (enExample) |
| IL (1) | IL162452A0 (enExample) |
| MA (1) | MA26300A1 (enExample) |
| MX (1) | MXPA04006121A (enExample) |
| NZ (1) | NZ533584A (enExample) |
| PL (1) | PL370835A1 (enExample) |
| PT (1) | PT1456218E (enExample) |
| RU (1) | RU2004122622A (enExample) |
| SI (1) | SI1456218T1 (enExample) |
| TW (1) | TW200301079A (enExample) |
| WO (1) | WO2003053988A2 (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CR6574A (es) | 2001-02-27 | 2004-10-28 | Syngenta Participations Ag | Sales de avermectinas substituidas en la posicion 4 con propiedades plaguicidas |
| EG23124A (en) | 2001-02-27 | 2004-04-28 | Syngenta Participations Ag | Avermectins substituted in the 4-position having pesticidal properties |
| AR036486A1 (es) | 2001-08-28 | 2004-09-15 | Syngenta Participations Ag | Derivados 4"-desoxi-4"-(s)-amino avermectina, composicion plaguicida, procedimiento para la preparacion de esa composicion, metodo para controlar plagas, y uso de estos derivados para preparar una composicion |
| AR040073A1 (es) * | 2002-05-07 | 2005-03-16 | Syngenta Participations Ag | Derivados de 4''-desoxi-4''-(s)-amido avermectina y su uso como plaguicidas |
| GB0302308D0 (en) * | 2003-01-31 | 2003-03-05 | Syngenta Participations Ag | Avermectin and avermectin monosaccharide derivatives substituted in the 4"- or 4'-position having pesticidal properties |
| GB0302309D0 (en) * | 2003-01-31 | 2003-03-05 | Syngenta Participations Ag | Avermectin monosaccharide derivatives substituted in the 4 -position having pesticidal properties |
| GB0302310D0 (en) * | 2003-01-31 | 2003-03-05 | Syngenta Participations Ag | Avermectin- and avermectin monosaccharide derivatives substituted in the 4"- or 4' - positionhaving pesticidal properties |
| GB0302547D0 (en) * | 2003-02-04 | 2003-03-12 | Syngenta Participations Ag | Avermectins and avermectin monosaccharide substituted in the 4'- and 4" position having pesticidal properties |
| FR2854071B1 (fr) * | 2003-04-25 | 2009-01-30 | Ethypharm Sa | Procede de dispersion de substances hydrosolubles ou hydrophiles dans un fluide a pression supercritique |
| GB0313937D0 (en) | 2003-06-16 | 2003-07-23 | Syngenta Participations Ag | Avermectin B1 monosaccharide derivatives having an aminosulfonyloxy substituentin the 4'-position |
| GB0320176D0 (en) * | 2003-08-28 | 2003-10-01 | Syngenta Participations Ag | Avermectins and avermectin monosaccharides substitued in the 4'-and 4"-positionhaving pesticidal properties |
| EP1849363A1 (en) * | 2006-03-09 | 2007-10-31 | Cheminova A/S | Synergistic combination of glutamate- and GABA-gated chloride agonist pesticide and at least one of Vitamin E or Niacin |
| AR081187A1 (es) | 2010-05-12 | 2012-07-04 | Merial Ltd | Formulaciones inyectables parasiticidas de levamisol y lactonas macrociclicas. metodo de preparacion. metodo de tratamiento. |
| AU2011338573B2 (en) | 2010-12-07 | 2016-07-28 | Boehringer Ingelheim Animal Health USA Inc. | Topical combination formulations of macrocyclic lactones with synthetic pyrethroids |
| CN103936755B (zh) * | 2014-04-08 | 2016-03-23 | 甘肃省农业科学院植物保护研究所 | 一种米尔贝霉素类似物及其制备方法和在农药中的应用 |
| RU2554074C1 (ru) * | 2014-04-18 | 2015-06-27 | Игорь Викторович Заварзин | Антипаразитарный агент |
| RU2554350C1 (ru) * | 2014-04-18 | 2015-06-27 | Игорь Викторович Заварзин | Инсектицидный агент |
| AU2017273857B2 (en) | 2016-06-01 | 2021-08-19 | Athira Pharma, Inc. | Compounds |
| CN108690108B (zh) * | 2018-07-27 | 2022-03-11 | 河北威远生物化工有限公司 | 一种磺酰胺基取代的阿维菌素B2a/B2b衍生物及其制备方法与应用 |
| US11351149B2 (en) | 2020-09-03 | 2022-06-07 | Pfizer Inc. | Nitrile-containing antiviral compounds |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4427663A (en) * | 1982-03-16 | 1984-01-24 | Merck & Co., Inc. | 4"-Keto-and 4"-amino-4"-deoxy avermectin compounds and substituted amino derivatives thereof |
-
2002
- 2002-12-19 TW TW091136626A patent/TW200301079A/zh unknown
- 2002-12-19 AR ARP020105025A patent/AR037938A1/es not_active Application Discontinuation
- 2002-12-20 AU AU2002361197A patent/AU2002361197A1/en not_active Abandoned
- 2002-12-20 EP EP02796710A patent/EP1456218B1/en not_active Expired - Lifetime
- 2002-12-20 PT PT02796710T patent/PT1456218E/pt unknown
- 2002-12-20 DK DK02796710T patent/DK1456218T3/da active
- 2002-12-20 US US10/498,858 patent/US6933260B2/en not_active Expired - Lifetime
- 2002-12-20 CN CNA028258835A patent/CN1608075A/zh active Pending
- 2002-12-20 AT AT02796710T patent/ATE397007T1/de active
- 2002-12-20 SI SI200230716T patent/SI1456218T1/sl unknown
- 2002-12-20 MX MXPA04006121A patent/MXPA04006121A/es unknown
- 2002-12-20 WO PCT/EP2002/014671 patent/WO2003053988A2/en not_active Ceased
- 2002-12-20 PL PL02370835A patent/PL370835A1/xx not_active Application Discontinuation
- 2002-12-20 JP JP2003554704A patent/JP2005513137A/ja active Pending
- 2002-12-20 CA CA002469905A patent/CA2469905A1/en not_active Abandoned
- 2002-12-20 HU HU0402290A patent/HUP0402290A2/hu unknown
- 2002-12-20 ES ES02796710T patent/ES2307823T3/es not_active Expired - Lifetime
- 2002-12-20 BR BR0215170-7A patent/BR0215170A/pt not_active Application Discontinuation
- 2002-12-20 DE DE60226895T patent/DE60226895D1/de not_active Expired - Lifetime
- 2002-12-20 IL IL16245202A patent/IL162452A0/xx unknown
- 2002-12-20 KR KR10-2004-7009873A patent/KR20040068335A/ko not_active Withdrawn
- 2002-12-20 NZ NZ533584A patent/NZ533584A/en unknown
- 2002-12-20 RU RU2004122622/04A patent/RU2004122622A/ru not_active Application Discontinuation
-
2004
- 2004-06-15 CO CO04055633A patent/CO5590963A2/es not_active Application Discontinuation
- 2004-07-19 MA MA27793A patent/MA26300A1/fr unknown
-
2008
- 2008-08-18 CY CY20081100877T patent/CY1108269T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR20040068335A (ko) | 2004-07-30 |
| CN1608075A (zh) | 2005-04-20 |
| CO5590963A2 (es) | 2005-12-30 |
| PT1456218E (pt) | 2008-08-06 |
| MA26300A1 (fr) | 2004-09-01 |
| ATE397007T1 (de) | 2008-06-15 |
| WO2003053988A2 (en) | 2003-07-03 |
| NZ533584A (en) | 2005-12-23 |
| US20050032717A1 (en) | 2005-02-10 |
| DE60226895D1 (de) | 2008-07-10 |
| BR0215170A (pt) | 2004-10-19 |
| PL370835A1 (en) | 2005-05-30 |
| AU2002361197A1 (en) | 2003-07-09 |
| SI1456218T1 (sl) | 2008-10-31 |
| DK1456218T3 (da) | 2008-08-04 |
| WO2003053988A3 (en) | 2003-12-11 |
| EP1456218A2 (en) | 2004-09-15 |
| MXPA04006121A (es) | 2004-10-29 |
| HUP0402290A2 (hu) | 2005-02-28 |
| US6933260B2 (en) | 2005-08-23 |
| EP1456218B1 (en) | 2008-05-28 |
| AR037938A1 (es) | 2004-12-22 |
| CY1108269T1 (el) | 2014-02-12 |
| IL162452A0 (en) | 2005-11-20 |
| CA2469905A1 (en) | 2003-07-03 |
| RU2004122622A (ru) | 2006-01-20 |
| ES2307823T3 (es) | 2008-12-01 |
| TW200301079A (en) | 2003-07-01 |
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