IL119321A - תולדות מילבמיצין 5 - אוקסים מותמרים בעמדה 13, ותכשירי הדברה המכילים אותן - Google Patents
תולדות מילבמיצין 5 - אוקסים מותמרים בעמדה 13, ותכשירי הדברה המכילים אותןInfo
- Publication number
- IL119321A IL119321A IL11932196A IL11932196A IL119321A IL 119321 A IL119321 A IL 119321A IL 11932196 A IL11932196 A IL 11932196A IL 11932196 A IL11932196 A IL 11932196A IL 119321 A IL119321 A IL 119321A
- Authority
- IL
- Israel
- Prior art keywords
- groups
- group
- carbon atoms
- substituents
- substituted
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 71
- FXWHFKOXMBTCMP-WMEDONTMSA-N milbemycin Natural products COC1C2OCC3=C/C=C/C(C)CC(=CCC4CC(CC5(O4)OC(C)C(C)C(OC(=O)C(C)CC(C)C)C5O)OC(=O)C(C=C1C)C23O)C FXWHFKOXMBTCMP-WMEDONTMSA-N 0.000 title description 26
- 230000000361 pesticidal effect Effects 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 187
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 141
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 72
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 46
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 24
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 23
- 125000003277 amino group Chemical group 0.000 claims abstract description 22
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 16
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract 2
- 229910052799 carbon Inorganic materials 0.000 claims description 145
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 123
- 125000001424 substituent group Chemical group 0.000 claims description 101
- -1 benzoylcarbonylamino groups Chemical group 0.000 claims description 79
- 125000000623 heterocyclic group Chemical group 0.000 claims description 48
- 125000003118 aryl group Chemical group 0.000 claims description 44
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- 238000000034 method Methods 0.000 claims description 29
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 25
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 24
- 239000001301 oxygen Substances 0.000 claims description 23
- 229910052760 oxygen Inorganic materials 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
- 229910052717 sulfur Inorganic materials 0.000 claims description 21
- 239000011593 sulfur Substances 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
- 125000006413 ring segment Chemical group 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 230000000749 insecticidal effect Effects 0.000 claims description 10
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- 125000004423 acyloxy group Chemical group 0.000 claims description 8
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 241000238631 Hexapoda Species 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 125000004443 haloalkoxycarbonylamino group Chemical group 0.000 claims description 4
- 230000001850 reproductive effect Effects 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
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- 244000045947 parasite Species 0.000 claims description 3
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 244000000013 helminth Species 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 7
- 125000005110 aryl thio group Chemical group 0.000 claims 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000005126 aryl alkyl carbonyl amino group Chemical group 0.000 claims 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 115
- 238000001819 mass spectrum Methods 0.000 description 104
- 238000006243 chemical reaction Methods 0.000 description 77
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 60
- 239000002904 solvent Substances 0.000 description 49
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 48
- 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 43
- 239000011734 sodium Substances 0.000 description 43
- 229910052708 sodium Inorganic materials 0.000 description 43
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 42
- 230000002829 reductive effect Effects 0.000 description 33
- 239000011541 reaction mixture Substances 0.000 description 27
- 239000007864 aqueous solution Substances 0.000 description 25
- 238000001704 evaporation Methods 0.000 description 25
- 230000008020 evaporation Effects 0.000 description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- 239000002253 acid Substances 0.000 description 20
- 239000000377 silicon dioxide Substances 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- 238000004440 column chromatography Methods 0.000 description 19
- 239000000243 solution Substances 0.000 description 17
- 239000003153 chemical reaction reagent Substances 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- 229910052736 halogen Inorganic materials 0.000 description 11
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000004094 surface-active agent Substances 0.000 description 8
- 239000003120 macrolide antibiotic agent Substances 0.000 description 7
- ZLBGSRMUSVULIE-GSMJGMFJSA-N milbemycin A3 Chemical class O1[C@H](C)[C@@H](C)CC[C@@]11O[C@H](C\C=C(C)\C[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 ZLBGSRMUSVULIE-GSMJGMFJSA-N 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- 241000196324 Embryophyta Species 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229910052759 nickel Inorganic materials 0.000 description 6
- 230000001473 noxious effect Effects 0.000 description 6
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- 241000258242 Siphonaptera Species 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
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- 239000000126 substance Substances 0.000 description 5
- 102100035353 Cyclin-dependent kinase 2-associated protein 1 Human genes 0.000 description 4
- LOTCVJJDZFMQGB-UHFFFAOYSA-N [N].[O].[S] Chemical compound [N].[O].[S] LOTCVJJDZFMQGB-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
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- 238000004821 distillation Methods 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- 239000012279 sodium borohydride Substances 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 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 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
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- 150000002367 halogens Chemical class 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
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- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
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- VOZIAWLUULBIPN-LRBNAKOISA-N milbemycin A4 Chemical compound C1C[C@H](C)[C@@H](CC)O[C@@]21O[C@H](C\C=C(C)\C[C@@H](C)\C=C\C=C/1[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\1)O)C[C@H]4C2 VOZIAWLUULBIPN-LRBNAKOISA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
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- 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 description 2
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- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
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- ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 1
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- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
-
- 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
- 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
- A01N43/02—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
- A01N43/24—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 two or more hetero atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biochemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Virology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Dentistry (AREA)
- Oncology (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Communicable Diseases (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25296595 | 1995-09-29 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL119321A0 IL119321A0 (en) | 1996-12-05 |
| IL119321A true IL119321A (he) | 2001-05-20 |
Family
ID=17244627
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL11932196A IL119321A (he) | 1995-09-29 | 1996-09-29 | תולדות מילבמיצין 5 - אוקסים מותמרים בעמדה 13, ותכשירי הדברה המכילים אותן |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US5861429A (he) |
| EP (1) | EP0765879B1 (he) |
| KR (1) | KR100300376B1 (he) |
| AT (1) | ATE199154T1 (he) |
| AU (1) | AU707152B2 (he) |
| CA (1) | CA2186650A1 (he) |
| CZ (1) | CZ288178B6 (he) |
| DE (1) | DE69611773T2 (he) |
| DK (1) | DK0765879T3 (he) |
| ES (1) | ES2155172T3 (he) |
| GR (1) | GR3035565T3 (he) |
| HU (1) | HU225226B1 (he) |
| IL (1) | IL119321A (he) |
| NO (1) | NO317090B1 (he) |
| NZ (1) | NZ299460A (he) |
| PT (1) | PT765879E (he) |
| RU (1) | RU2128181C1 (he) |
| ZA (1) | ZA968183B (he) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6492372B1 (en) | 1999-01-22 | 2002-12-10 | Elan Pharmaceuticals, Inc. | Heteroaryl, heterocyclic and aryl compounds which inhibit leukocyte adhesion mediated by VLA-4 |
| CA2357781A1 (en) | 1999-01-22 | 2000-07-27 | Elan Pharmaceuticals, Inc. | Multicyclic compounds which inhibit leukocyte adhesion mediated by vla-4 |
| IL143928A0 (en) * | 1999-01-22 | 2002-04-21 | Elan Pharm Inc | Fused ring heteroaryl and heterocyclic compounds which inhibit leukocyte adhesion mediated by vla-4 |
| US6436904B1 (en) | 1999-01-25 | 2002-08-20 | Elan Pharmaceuticals, Inc. | Compounds which inhibit leukocyte adhesion mediated by VLA-4 |
| CA2361162A1 (en) | 1999-03-01 | 2000-09-08 | Elan Pharmaceuticals, Inc. | Alpha-aminoacetic acid derivatives useful as alpha 4 beta 7-receptor antagonists |
| DK1276748T3 (da) | 2000-04-27 | 2006-03-20 | Sankyo Lifetech Company Ltd | 13-substituerede milbemycinderivater, deres fremstilling og deres anvendelse over for insekter og andre skadedyr |
| RU2195280C1 (ru) * | 2001-05-21 | 2002-12-27 | Всероссийский научно-исследовательский институт гельминтологии им. К.И. Скрябина | Антигельминтное средство |
| IL161560A0 (en) | 2001-10-25 | 2004-09-27 | Sankyo Lifetech Company Ltd | Anthelmintic compositions containing milbemycin derivatives |
| TWI281470B (en) * | 2002-05-24 | 2007-05-21 | Elan Pharm Inc | Heterocyclic compounds which inhibit leukocyte adhesion mediated by alpha4 integrins |
| TW200307671A (en) * | 2002-05-24 | 2003-12-16 | Elan Pharm Inc | Heteroaryl compounds which inhibit leukocyte adhesion mediated by α 4 integrins |
| JP4373080B2 (ja) * | 2002-12-24 | 2009-11-25 | 三井化学アグロ株式会社 | ミルベマイシン類の精製法 |
| WO2005075070A1 (ja) * | 2004-02-05 | 2005-08-18 | Nippon Shokubai Co., Ltd. | 粒子状吸水剤及びその製造方法並びに吸水性物品 |
| RU2355370C2 (ru) * | 2004-02-05 | 2009-05-20 | Ниппон Шокубаи Ко., Лтд. | Твердый водопоглощающий реагент и способ его изготовления, и водопоглощающее изделие |
| TWI353360B (en) | 2005-04-07 | 2011-12-01 | Nippon Catalytic Chem Ind | Production process of polyacrylic acid (salt) wate |
| BRPI0616643A2 (pt) * | 2005-09-29 | 2011-06-28 | Elan Pharm Inc | compostos de carbamato que inibem a adesão leucocitária mediada por vla-4 |
| NZ567270A (en) * | 2005-09-29 | 2011-06-30 | Elan Pharm Inc | Pyrimidinyl amide compounds which inhibit leukocyte adhesion mediated by VLA-4 |
| TWI394789B (zh) | 2005-12-22 | 2013-05-01 | Nippon Catalytic Chem Ind | 吸水性樹脂組成物及其製造方法、吸收性物品 |
| KR20080100271A (ko) * | 2006-02-27 | 2008-11-14 | 엘란 파마슈티칼스, 인크. | Ｖｌａ-4에 의해 매개되는 백혈구 부착을 억제하는 피리미디닐 술폰아미드 화합물 |
| EP1837348B9 (en) | 2006-03-24 | 2020-01-08 | Nippon Shokubai Co.,Ltd. | Water-absorbing resin and method for manufacturing the same |
| EP2424841A1 (en) * | 2009-04-27 | 2012-03-07 | Elan Pharmaceuticals Inc. | Pyridinone antagonists of alpha-4 integrins |
| US8952116B2 (en) | 2009-09-29 | 2015-02-10 | Nippon Shokubai Co., Ltd. | Particulate water absorbent and process for production thereof |
Family Cites Families (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3950360A (en) * | 1972-06-08 | 1976-04-13 | Sankyo Company Limited | Antibiotic substances |
| JPS4914624A (he) * | 1972-06-08 | 1974-02-08 | ||
| US4201861A (en) * | 1977-10-03 | 1980-05-06 | Merck & Co., Inc. | Acyl derivatives of C-076 compounds |
| US4206205A (en) * | 1977-10-03 | 1980-06-03 | Merck & Co., Inc. | Monosaccharide and aglycone derivatives of C-076 |
| US4173571A (en) * | 1977-12-19 | 1979-11-06 | Merck & Co., Inc. | 13-Halo and 13-deoxy derivatives of C-076 compounds |
| US4171314A (en) * | 1977-12-19 | 1979-10-16 | Merck & Co., Inc. | 13-Halo and 13-deoxy C-076 compounds |
| US4203976A (en) * | 1978-08-02 | 1980-05-20 | Merck & Co., Inc. | Sugar derivatives of C-076 compounds |
| JPS5632481A (en) * | 1979-08-23 | 1981-04-01 | Sankyo Co Ltd | Antibiotic b-41d, its preparation, and acaricide and anthelminthic agent and repellent containing the same as active constituent |
| US4289760A (en) * | 1980-05-02 | 1981-09-15 | Merck & Co., Inc. | 23-Keto derivatives of C-076 compounds |
| US4457920A (en) * | 1981-09-03 | 1984-07-03 | Merck & Co., Inc. | 4a-Substituted avermectin compounds |
| US4423209A (en) * | 1982-02-26 | 1983-12-27 | Merck & Co., Inc. | Processes for the interconversion of avermectin compounds |
| JPS59108785A (ja) * | 1982-11-25 | 1984-06-23 | Sankyo Co Ltd | ミルベマイシン類の５−オキシム誘導体 |
| US4579864A (en) * | 1984-06-11 | 1986-04-01 | Merck & Co., Inc. | Avermectin and milbemycin 13-keto, 13-imino and 13-amino derivatives |
| US4547491A (en) * | 1984-07-18 | 1985-10-15 | Merck & Co., Inc. | C-8A-Oxo-avermectin and milbemycin derivatives, pharmaceutical compositions and method of use |
| ES8802229A1 (es) * | 1985-04-30 | 1988-04-16 | Glaxo Group Ltd | Un procedimiento para preparar nuevos derivados lactonicos macrociclicos. |
| JPS6289685A (ja) * | 1985-05-31 | 1987-04-24 | Sankyo Co Ltd | １３−ハロゲンミルベマイシン誘導体 |
| US4668696A (en) * | 1985-07-29 | 1987-05-26 | Merck & Co., Inc. | Novel averonectin fermentation product of a microorganism with anthelmintic activity |
| US4778809A (en) * | 1985-08-23 | 1988-10-18 | Ciba-Geigy Corporation | 5-esters of milbemycins for controlling parasitic pests |
| ES2019932B3 (es) * | 1986-03-25 | 1991-07-16 | Sankyo Co | Compuestos macrolidos. |
| GB8815967D0 (en) * | 1988-07-05 | 1988-08-10 | Pfizer Ltd | Antiparasitic agents |
| US5428034A (en) * | 1988-09-02 | 1995-06-27 | Sankyo Co., Ltd. | Milbemycin derivatives, their preparation and their use |
| CA2085703C (en) * | 1991-12-18 | 2001-05-01 | Toshiaki Yanai | 13-(substituted thio) acetoxymilbemycin derivatives, their preparation and their agrochemical uses |
| GB9201505D0 (en) * | 1992-01-24 | 1992-03-11 | Pfizer Ltd | Antiparasitic agents |
| GB9205051D0 (en) * | 1992-03-09 | 1992-04-22 | Cancer Res Campaign Tech | Pyrrolobenzodiazepine derivatives,their preparation,and compositions containing them |
| US5614470A (en) * | 1994-04-01 | 1997-03-25 | Sankyo Company, Limited | 13-substituted milbemycin derivatives, their preparation and their use |
| AU3935495A (en) * | 1994-11-24 | 1996-06-17 | Sankyo Company Limited | 13-etherified milbemycin derivative with insecticidal activity |
-
1996
- 1996-09-27 DK DK96307092T patent/DK0765879T3/da active
- 1996-09-27 ES ES96307092T patent/ES2155172T3/es not_active Expired - Lifetime
- 1996-09-27 CZ CZ19962862A patent/CZ288178B6/cs not_active IP Right Cessation
- 1996-09-27 AU AU65861/96A patent/AU707152B2/en not_active Ceased
- 1996-09-27 DE DE69611773T patent/DE69611773T2/de not_active Expired - Lifetime
- 1996-09-27 EP EP96307092A patent/EP0765879B1/en not_active Expired - Lifetime
- 1996-09-27 CA CA002186650A patent/CA2186650A1/en not_active Abandoned
- 1996-09-27 NO NO19964090A patent/NO317090B1/no not_active IP Right Cessation
- 1996-09-27 NZ NZ299460A patent/NZ299460A/en unknown
- 1996-09-27 AT AT96307092T patent/ATE199154T1/de not_active IP Right Cessation
- 1996-09-27 ZA ZA968183A patent/ZA968183B/xx unknown
- 1996-09-27 HU HU9602678A patent/HU225226B1/hu not_active IP Right Cessation
- 1996-09-27 PT PT96307092T patent/PT765879E/pt unknown
- 1996-09-29 IL IL11932196A patent/IL119321A/he not_active IP Right Cessation
- 1996-09-30 RU RU96120138/04A patent/RU2128181C1/ru not_active IP Right Cessation
- 1996-09-30 US US08/723,835 patent/US5861429A/en not_active Expired - Fee Related
- 1996-09-30 KR KR1019960042886A patent/KR100300376B1/ko not_active Expired - Fee Related
-
2001
- 2001-03-13 GR GR20010400411T patent/GR3035565T3/el not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AU707152B2 (en) | 1999-07-01 |
| US5861429A (en) | 1999-01-19 |
| AU6586196A (en) | 1997-04-10 |
| KR100300376B1 (ko) | 2001-10-22 |
| ZA968183B (en) | 1997-04-25 |
| EP0765879B1 (en) | 2001-02-14 |
| GR3035565T3 (en) | 2001-06-29 |
| NO964090L (no) | 1997-04-01 |
| HUP9602678A1 (en) | 1997-11-28 |
| DK0765879T3 (da) | 2001-03-19 |
| NZ299460A (en) | 1997-12-19 |
| ATE199154T1 (de) | 2001-02-15 |
| PT765879E (pt) | 2001-05-31 |
| RU2128181C1 (ru) | 1999-03-27 |
| HU225226B1 (en) | 2006-08-28 |
| CZ286296A3 (en) | 1997-04-16 |
| CZ288178B6 (en) | 2001-05-16 |
| EP0765879A1 (en) | 1997-04-02 |
| CA2186650A1 (en) | 1997-03-30 |
| DE69611773T2 (de) | 2001-09-13 |
| KR970015592A (ko) | 1997-04-28 |
| NO964090D0 (no) | 1996-09-27 |
| ES2155172T3 (es) | 2001-05-01 |
| HK1003937A1 (en) | 1998-11-13 |
| DE69611773D1 (de) | 2001-03-22 |
| NO317090B1 (no) | 2004-08-02 |
| HU9602678D0 (en) | 1996-11-28 |
| IL119321A0 (en) | 1996-12-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FF | Patent granted | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| HP | Change in proprietorship |
Owner name: NOVARTIS ANIMAL HEALTH K.K. Free format text: FORMER OWNER:SANKYO LIFETECH COMPANY LIMITED |
|
| MM9K | Patent not in force due to non-payment of renewal fees |