JP4750698B2 - アベルメクチンｂ１単糖誘導体 - Google Patents
アベルメクチンｂ１単糖誘導体 Download PDFInfo
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- JP4750698B2 JP4750698B2 JP2006515942A JP2006515942A JP4750698B2 JP 4750698 B2 JP4750698 B2 JP 4750698B2 JP 2006515942 A JP2006515942 A JP 2006515942A JP 2006515942 A JP2006515942 A JP 2006515942A JP 4750698 B2 JP4750698 B2 JP 4750698B2
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- spp
- alkyl
- alkoxy
- heterocyclyl
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- NJTGMYOUKBELLQ-NVQQORPBSA-N avermectin b1 monosaccharide Chemical class O1C(C)C(O)C(OC)CC1O[C@@H]1C(/C)=C/C[C@@H](O[C@]2(C3)C=C[C@H](C)[C@@H](C(C)C)O2)C[C@@H]3OC(=O)[C@@H]([C@]23O)C=C(C)[C@@H](O)[C@H]3OC\C2=C/C=C/[C@@H]1C NJTGMYOUKBELLQ-NVQQORPBSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 198
- 125000000217 alkyl group Chemical group 0.000 claims description 97
- -1 methylenedioxy Chemical group 0.000 claims description 97
- 239000000203 mixture Substances 0.000 claims description 88
- 125000004432 carbon atom Chemical group C* 0.000 claims description 65
- 238000000034 method Methods 0.000 claims description 36
- 229910052736 halogen Inorganic materials 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- 150000002367 halogens Chemical class 0.000 claims description 31
- 125000003118 aryl group Chemical group 0.000 claims description 29
- 125000001424 substituent group Chemical group 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 27
- 238000002360 preparation method Methods 0.000 claims description 25
- 125000000623 heterocyclic group Chemical group 0.000 claims description 24
- 241000607479 Yersinia pestis Species 0.000 claims description 23
- 239000004480 active ingredient Substances 0.000 claims description 20
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000004104 aryloxy group Chemical group 0.000 claims description 19
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 19
- 150000003839 salts Chemical group 0.000 claims description 19
- 230000000749 insecticidal effect Effects 0.000 claims description 17
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 15
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 14
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 13
- 125000004414 alkyl thio group Chemical group 0.000 claims description 13
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 12
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 125000004643 (C1-C12) haloalkoxy group Chemical group 0.000 claims description 11
- 125000004641 (C1-C12) haloalkyl group Chemical group 0.000 claims description 11
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 11
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 11
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 11
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 11
- 239000000463 material Substances 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 9
- 239000002671 adjuvant Substances 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 6
- 125000004450 alkenylene group Chemical group 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 238000006467 substitution reaction Methods 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000005149 cycloalkylsulfinyl group Chemical group 0.000 claims description 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 3
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 3
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims description 3
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims description 3
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 3
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 238000000227 grinding Methods 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
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 150000003254 radicals Chemical class 0.000 description 27
- 150000002431 hydrogen Chemical class 0.000 description 21
- 230000000694 effects Effects 0.000 description 20
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 19
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 17
- 229910052794 bromium Inorganic materials 0.000 description 16
- 239000000460 chlorine Substances 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 229910052801 chlorine Inorganic materials 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 14
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 14
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 14
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000011734 sodium Substances 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 239000011737 fluorine Substances 0.000 description 10
- 229910052731 fluorine Inorganic materials 0.000 description 10
- 230000009467 reduction Effects 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000839 emulsion Substances 0.000 description 9
- 239000004094 surface-active agent Substances 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 8
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 8
- 241000244206 Nematoda Species 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 239000000654 additive Substances 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 125000006239 protecting group Chemical group 0.000 description 8
- 229940126062 Compound A Drugs 0.000 description 7
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 235000019441 ethanol Nutrition 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 241000238631 Hexapoda Species 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 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 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
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- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
- 239000005660 Abamectin Substances 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 241000256248 Spodoptera Species 0.000 description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 5
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
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- 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 description 5
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
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Classifications
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- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- 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
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- Animal Behavior & Ethology (AREA)
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- Chemical Kinetics & Catalysis (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0313937.5A GB0313937D0 (en) | 2003-06-16 | 2003-06-16 | Avermectin B1 monosaccharide derivatives having an aminosulfonyloxy substituentin the 4'-position |
| GB0313937.5 | 2003-06-16 | ||
| PCT/EP2004/006442 WO2004111070A1 (en) | 2003-06-16 | 2004-06-15 | Avermectin b1 monosaccharide derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2006527724A JP2006527724A (ja) | 2006-12-07 |
| JP2006527724A5 JP2006527724A5 (enExample) | 2011-05-12 |
| JP4750698B2 true JP4750698B2 (ja) | 2011-08-17 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006515942A Expired - Fee Related JP4750698B2 (ja) | 2003-06-16 | 2004-06-15 | アベルメクチンｂ１単糖誘導体 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US7521429B2 (enExample) |
| EP (1) | EP1638984B1 (enExample) |
| JP (1) | JP4750698B2 (enExample) |
| AR (1) | AR045693A1 (enExample) |
| AT (1) | ATE370157T1 (enExample) |
| CY (1) | CY1106940T1 (enExample) |
| DE (1) | DE602004008281T2 (enExample) |
| DK (1) | DK1638984T3 (enExample) |
| ES (1) | ES2293276T3 (enExample) |
| GB (1) | GB0313937D0 (enExample) |
| PL (1) | PL1638984T3 (enExample) |
| PT (1) | PT1638984E (enExample) |
| SI (1) | SI1638984T1 (enExample) |
| TW (1) | TW200504088A (enExample) |
| WO (1) | WO2004111070A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200538461A (en) * | 2004-04-07 | 2005-12-01 | Syngenta Participations Ag | Avermectin and avermectin monosaccharide substituted in the 4"-and 4'-position respectively |
| DK2568980T3 (en) | 2010-05-12 | 2015-11-30 | Merial Inc | INJECTABLE PARASITICIDE FORMULATIONS OF LEVAMISOL AND MACROCYCLIC LACTONS |
| AU2011338573B2 (en) | 2010-12-07 | 2016-07-28 | Boehringer Ingelheim Animal Health USA Inc. | Topical combination formulations of macrocyclic lactones with synthetic pyrethroids |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4622313A (en) * | 1985-08-01 | 1986-11-11 | Merck & Co., Inc. | O-sulfate derivatives of avermectins and milbemycins having improved water solubility |
| US4833168A (en) * | 1986-10-03 | 1989-05-23 | Merck & Co., Inc. | Avermectin reformatsky adducts |
| JPH0278683A (ja) * | 1988-07-22 | 1990-03-19 | Merck & Co Inc | アルキルアベルメクチン誘導体 |
| JPH02212491A (ja) * | 1988-12-23 | 1990-08-23 | Merck & Co Inc | アベルメクチン誘導体 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5208222A (en) * | 1991-03-28 | 1993-05-04 | Merck & Co., Inc. | 4"-and 4'-alkylthio avermectin derivatives |
| GB9205007D0 (en) * | 1992-03-07 | 1992-04-22 | Pfizer Ltd | Antiparasitic agents |
| AR037938A1 (es) * | 2001-12-21 | 2004-12-22 | Syngenta Participations Ag | Derivados de avermectina b1 que tienen un substituyente de aminosulfoniloxilo en la posicion 4'' |
-
2003
- 2003-06-16 GB GBGB0313937.5A patent/GB0313937D0/en not_active Ceased
-
2004
- 2004-06-14 AR ARP040102059A patent/AR045693A1/es unknown
- 2004-06-14 TW TW093117009A patent/TW200504088A/zh unknown
- 2004-06-15 AT AT04739912T patent/ATE370157T1/de active
- 2004-06-15 US US10/560,390 patent/US7521429B2/en not_active Expired - Lifetime
- 2004-06-15 DE DE602004008281T patent/DE602004008281T2/de not_active Expired - Lifetime
- 2004-06-15 SI SI200430477T patent/SI1638984T1/sl unknown
- 2004-06-15 WO PCT/EP2004/006442 patent/WO2004111070A1/en not_active Ceased
- 2004-06-15 JP JP2006515942A patent/JP4750698B2/ja not_active Expired - Fee Related
- 2004-06-15 PL PL04739912T patent/PL1638984T3/pl unknown
- 2004-06-15 EP EP04739912A patent/EP1638984B1/en not_active Expired - Lifetime
- 2004-06-15 DK DK04739912T patent/DK1638984T3/da active
- 2004-06-15 ES ES04739912T patent/ES2293276T3/es not_active Expired - Lifetime
- 2004-06-15 PT PT04739912T patent/PT1638984E/pt unknown
-
2007
- 2007-10-19 CY CY20071101344T patent/CY1106940T1/el unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4622313A (en) * | 1985-08-01 | 1986-11-11 | Merck & Co., Inc. | O-sulfate derivatives of avermectins and milbemycins having improved water solubility |
| US4833168A (en) * | 1986-10-03 | 1989-05-23 | Merck & Co., Inc. | Avermectin reformatsky adducts |
| JPH0278683A (ja) * | 1988-07-22 | 1990-03-19 | Merck & Co Inc | アルキルアベルメクチン誘導体 |
| JPH02212491A (ja) * | 1988-12-23 | 1990-08-23 | Merck & Co Inc | アベルメクチン誘導体 |
Also Published As
| Publication number | Publication date |
|---|---|
| PT1638984E (pt) | 2007-11-09 |
| ATE370157T1 (de) | 2007-09-15 |
| US20060229263A1 (en) | 2006-10-12 |
| DE602004008281D1 (en) | 2007-09-27 |
| ES2293276T3 (es) | 2008-03-16 |
| JP2006527724A (ja) | 2006-12-07 |
| CY1106940T1 (el) | 2012-09-26 |
| TW200504088A (en) | 2005-02-01 |
| DE602004008281T2 (de) | 2008-05-15 |
| PL1638984T3 (pl) | 2008-02-29 |
| WO2004111070A1 (en) | 2004-12-23 |
| DK1638984T3 (da) | 2007-12-03 |
| EP1638984A1 (en) | 2006-03-29 |
| GB0313937D0 (en) | 2003-07-23 |
| AR045693A1 (es) | 2005-11-09 |
| EP1638984B1 (en) | 2007-08-15 |
| US7521429B2 (en) | 2009-04-21 |
| SI1638984T1 (sl) | 2007-12-31 |
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