NO892087L - Fremgangsmaate for fremstilling av nye avermectiner med enspaltet furanring og en 8alfa -hydroxygruppe. - Google Patents
Fremgangsmaate for fremstilling av nye avermectiner med enspaltet furanring og en 8alfa -hydroxygruppe.Info
- Publication number
- NO892087L NO892087L NO89892087A NO892087A NO892087L NO 892087 L NO892087 L NO 892087L NO 89892087 A NO89892087 A NO 89892087A NO 892087 A NO892087 A NO 892087A NO 892087 L NO892087 L NO 892087L
- Authority
- NO
- Norway
- Prior art keywords
- deepoxy
- avermectin
- blb
- solution
- hydroxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 25
- -1 HYDROXY GROUP Chemical group 0.000 title description 14
- 238000002360 preparation method Methods 0.000 title description 11
- 229940058299 avermectines Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 85
- 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 claims abstract description 45
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 18
- 230000008569 process Effects 0.000 claims abstract description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 62
- 239000005660 Abamectin Substances 0.000 claims description 28
- 239000012279 sodium borohydride Substances 0.000 claims description 18
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 18
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 9
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 9
- TWCMVXMQHSVIOJ-UHFFFAOYSA-N Aglycone of yadanzioside D Natural products COC(=O)C12OCC34C(CC5C(=CC(O)C(O)C5(C)C3C(O)C1O)C)OC(=O)C(OC(=O)C)C24 TWCMVXMQHSVIOJ-UHFFFAOYSA-N 0.000 claims description 8
- PLMKQQMDOMTZGG-UHFFFAOYSA-N Astrantiagenin E-methylester Natural products CC12CCC(O)C(C)(CO)C1CCC1(C)C2CC=C2C3CC(C)(C)CCC3(C(=O)OC)CCC21C PLMKQQMDOMTZGG-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- PFOARMALXZGCHY-UHFFFAOYSA-N homoegonol Natural products C1=C(OC)C(OC)=CC=C1C1=CC2=CC(CCCO)=CC(OC)=C2O1 PFOARMALXZGCHY-UHFFFAOYSA-N 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims 2
- 239000003638 chemical reducing agent Substances 0.000 claims 2
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 150000002772 monosaccharides Chemical class 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract description 11
- 239000003096 antiparasitic agent Substances 0.000 abstract description 7
- 241000607479 Yersinia pestis Species 0.000 abstract description 6
- 229940125687 antiparasitic agent Drugs 0.000 abstract description 4
- 239000002917 insecticide Substances 0.000 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 185
- 239000000243 solution Substances 0.000 description 107
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 77
- 239000011541 reaction mixture Substances 0.000 description 44
- 239000000203 mixture Substances 0.000 description 42
- 235000017557 sodium bicarbonate Nutrition 0.000 description 38
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 38
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
- 239000010410 layer Substances 0.000 description 36
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
- 239000012267 brine Substances 0.000 description 29
- 238000006243 chemical reaction Methods 0.000 description 29
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 29
- 239000000047 product Substances 0.000 description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 23
- 239000000741 silica gel Substances 0.000 description 23
- 229910002027 silica gel Inorganic materials 0.000 description 23
- 238000012746 preparative thin layer chromatography Methods 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 19
- 241001465754 Metazoa Species 0.000 description 18
- 239000012044 organic layer Substances 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000012071 phase Substances 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 12
- 239000000463 material Substances 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 235000019198 oils Nutrition 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- 239000007858 starting material Substances 0.000 description 11
- 244000045947 parasite Species 0.000 description 10
- 238000002953 preparative HPLC Methods 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 238000000746 purification Methods 0.000 description 9
- 241000238631 Hexapoda Species 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 239000011780 sodium chloride Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
- 239000008346 aqueous phase Substances 0.000 description 7
- 238000011282 treatment Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
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- 238000009472 formulation Methods 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 125000003412 L-alanyl group Chemical group [H]N([H])[C@@](C([H])([H])[H])(C(=O)[*])[H] 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 238000000855 fermentation Methods 0.000 description 5
- 230000004151 fermentation Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 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 description 5
- 125000003808 silyl group Chemical class [H][Si]([H])([H])[*] 0.000 description 5
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- RCBVKBFIWMOMHF-UHFFFAOYSA-L hydroxy-(hydroxy(dioxo)chromio)oxy-dioxochromium;pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1.O[Cr](=O)(=O)O[Cr](O)(=O)=O RCBVKBFIWMOMHF-UHFFFAOYSA-L 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
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- 241000238421 Arthropoda Species 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 241000244206 Nematoda Species 0.000 description 3
- 241001674048 Phthiraptera Species 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
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- 239000003708 ampul Substances 0.000 description 2
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- DKVBOUDTNWVDEP-NJCHZNEYSA-N teicoplanin aglycone Chemical compound N([C@H](C(N[C@@H](C1=CC(O)=CC(O)=C1C=1C(O)=CC=C2C=1)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)OC=1C=C3C=C(C=1O)OC1=CC=C(C=C1Cl)C[C@H](C(=O)N1)NC([C@H](N)C=4C=C(O5)C(O)=CC=4)=O)C(=O)[C@@H]2NC(=O)[C@@H]3NC(=O)[C@@H]1C1=CC5=CC(O)=C1 DKVBOUDTNWVDEP-NJCHZNEYSA-N 0.000 description 2
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- VOVZXURTCKPRDQ-CQSZACIVSA-N n-[4-[chloro(difluoro)methoxy]phenyl]-6-[(3r)-3-hydroxypyrrolidin-1-yl]-5-(1h-pyrazol-5-yl)pyridine-3-carboxamide Chemical compound C1[C@H](O)CCN1C1=NC=C(C(=O)NC=2C=CC(OC(F)(F)Cl)=CC=2)C=C1C1=CC=NN1 VOVZXURTCKPRDQ-CQSZACIVSA-N 0.000 description 1
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- RNVYQYLELCKWAN-UHFFFAOYSA-N solketal Chemical compound CC1(C)OCC(CO)O1 RNVYQYLELCKWAN-UHFFFAOYSA-N 0.000 description 1
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- 210000004304 subcutaneous tissue Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
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- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
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- 235000015099 wheat brans Nutrition 0.000 description 1
Classifications
-
- 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
- A01N43/90—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
-
- 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
- A61P31/04—Antibacterial agents
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Genetics & Genomics (AREA)
- Environmental Sciences (AREA)
- Tropical Medicine & Parasitology (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Zoology (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Saccharide Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Polyesters Or Polycarbonates (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/198,271 US5008250A (en) | 1988-05-25 | 1988-05-25 | Avermectins with a cleaved furan ring and an 8a hydroxy group |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO892087D0 NO892087D0 (no) | 1989-05-24 |
| NO892087L true NO892087L (no) | 1989-11-27 |
Family
ID=22732675
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO89892087A NO892087L (no) | 1988-05-25 | 1989-05-24 | Fremgangsmaate for fremstilling av nye avermectiner med enspaltet furanring og en 8alfa -hydroxygruppe. |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US5008250A (ja) |
| EP (1) | EP0343715B1 (ja) |
| JP (1) | JPH0641468B2 (ja) |
| KR (1) | KR900018110A (ja) |
| AT (1) | ATE121092T1 (ja) |
| AU (1) | AU612841B2 (ja) |
| DE (1) | DE68922136D1 (ja) |
| DK (1) | DK251289A (ja) |
| FI (1) | FI892531A (ja) |
| IL (1) | IL90314A0 (ja) |
| NO (1) | NO892087L (ja) |
| NZ (1) | NZ229118A (ja) |
| PT (1) | PT90621B (ja) |
| ZA (1) | ZA893917B (ja) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5541075A (en) * | 1993-02-05 | 1996-07-30 | Heska Corporation | Carbohydrate-based vaccine and diagnostic reagent for trichinosis |
| US5707817A (en) * | 1993-02-05 | 1998-01-13 | Colorado State University Research Foundation | Carbohydrate-based vaccine and diagnostic reagent for trichinosis |
| GB0302309D0 (en) * | 2003-01-31 | 2003-03-05 | Syngenta Participations Ag | Avermectin monosaccharide derivatives substituted in the 4 -position having pesticidal properties |
| CN103242338B (zh) * | 2013-05-07 | 2015-03-04 | 东北农业大学 | 一种大环内酯类化合物及其制备方法和应用 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4093629A (en) * | 1977-04-11 | 1978-06-06 | Merck & Co., Inc. | Derivatives of antibiotic substance milbemycin and processes therefor |
| US4173571A (en) * | 1977-12-19 | 1979-11-06 | Merck & Co., Inc. | 13-Halo and 13-deoxy derivatives of C-076 compounds |
| JPS5931510B2 (ja) * | 1979-09-03 | 1984-08-02 | 東レ株式会社 | ５，６，７−トリノル−４，８−インタ−ｍ−フエニレンＰＧＩ↓２誘導体 |
| US4285963A (en) * | 1980-08-07 | 1981-08-25 | Merck & Co., Inc. | Novel derivatives of C-076 compounds |
| JPS57139079A (en) * | 1981-02-23 | 1982-08-27 | Sankyo Co Ltd | 8,9-epoxy derivative of antibiotic substance b-41 and its preparation |
| US4333925A (en) * | 1981-05-11 | 1982-06-08 | Merck & Co., Inc. | Derivatives of C-076 compounds |
| DK165119C (da) * | 1984-06-05 | 1993-03-01 | American Cyanamid Co | Antibiotiske forbindelser betegnet ll-f28249alfa, beta, gamma, delta, epsilon, zeta, eta, theta, iota, kappa, my og ny og pharmaceutisk or pharmakologisk acceptable salte deraf samt fremgangsmaade til deres fremstilling |
| US4547491A (en) * | 1984-07-18 | 1985-10-15 | Merck & Co., Inc. | C-8A-Oxo-avermectin and milbemycin derivatives, pharmaceutical compositions and method of use |
| US4789684A (en) * | 1985-05-02 | 1988-12-06 | Merck & Co., Inc. | Anthelmintic fermentation products of microorganisms |
| US4873224A (en) * | 1988-05-23 | 1989-10-10 | Merck & Co., Inc. | Avermectin derivatives |
-
1988
- 1988-05-25 US US07/198,271 patent/US5008250A/en not_active Expired - Fee Related
-
1989
- 1989-05-15 NZ NZ229118A patent/NZ229118A/en unknown
- 1989-05-16 IL IL90314A patent/IL90314A0/xx unknown
- 1989-05-17 EP EP89201237A patent/EP0343715B1/en not_active Expired - Lifetime
- 1989-05-17 DE DE68922136T patent/DE68922136D1/de not_active Expired - Lifetime
- 1989-05-17 AT AT89201237T patent/ATE121092T1/de active
- 1989-05-22 AU AU35045/89A patent/AU612841B2/en not_active Ceased
- 1989-05-22 PT PT90621A patent/PT90621B/pt not_active IP Right Cessation
- 1989-05-24 FI FI892531A patent/FI892531A/fi not_active Application Discontinuation
- 1989-05-24 KR KR1019890006927A patent/KR900018110A/ko not_active Application Discontinuation
- 1989-05-24 NO NO89892087A patent/NO892087L/no unknown
- 1989-05-24 DK DK251289A patent/DK251289A/da not_active Application Discontinuation
- 1989-05-24 ZA ZA893917A patent/ZA893917B/xx unknown
- 1989-05-25 JP JP1130292A patent/JPH0641468B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US5008250A (en) | 1991-04-16 |
| KR900018110A (ko) | 1990-12-20 |
| JPH0219382A (ja) | 1990-01-23 |
| DK251289D0 (da) | 1989-05-24 |
| EP0343715A2 (en) | 1989-11-29 |
| PT90621B (pt) | 1994-10-31 |
| DE68922136D1 (de) | 1995-05-18 |
| AU3504589A (en) | 1989-11-30 |
| EP0343715B1 (en) | 1995-04-12 |
| EP0343715A3 (en) | 1991-03-20 |
| NZ229118A (en) | 1992-02-25 |
| IL90314A0 (en) | 1989-12-15 |
| PT90621A (pt) | 1989-11-30 |
| FI892531A (fi) | 1989-11-26 |
| ATE121092T1 (de) | 1995-04-15 |
| FI892531A0 (fi) | 1989-05-24 |
| NO892087D0 (no) | 1989-05-24 |
| JPH0641468B2 (ja) | 1994-06-01 |
| AU612841B2 (en) | 1991-07-18 |
| DK251289A (da) | 1989-11-27 |
| ZA893917B (en) | 1990-02-28 |
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| US4171314A (en) | 13-Halo and 13-deoxy C-076 compounds | |
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