NZ186852A - 13-hydroxy,-bromo,and-acetoxy-milbemycins and parasiticidal compositions - Google Patents
13-hydroxy,-bromo,and-acetoxy-milbemycins and parasiticidal compositionsInfo
- Publication number
- NZ186852A NZ186852A NZ186852A NZ18685278A NZ186852A NZ 186852 A NZ186852 A NZ 186852A NZ 186852 A NZ186852 A NZ 186852A NZ 18685278 A NZ18685278 A NZ 18685278A NZ 186852 A NZ186852 A NZ 186852A
- Authority
- NZ
- New Zealand
- Prior art keywords
- milbemycin
- hydroxy
- bromo
- parasites
- acetoxy
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 12
- 230000000590 parasiticidal effect Effects 0.000 title description 2
- 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 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 13
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 12
- 241001465754 Metazoa Species 0.000 claims description 9
- 244000045947 parasite Species 0.000 claims description 9
- 241000282414 Homo sapiens Species 0.000 claims description 7
- 238000009472 formulation Methods 0.000 claims description 6
- 208000015181 infectious disease Diseases 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- -1 alkali metal acetate Chemical class 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 230000002141 anti-parasite Effects 0.000 claims description 3
- 239000003096 antiparasitic agent Substances 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 3
- 239000003981 vehicle Substances 0.000 claims 3
- 208000030852 Parasitic disease Diseases 0.000 claims 2
- 235000019483 Peanut oil Nutrition 0.000 claims 1
- 230000000397 acetylating effect Effects 0.000 claims 1
- 239000011149 active material Substances 0.000 claims 1
- 229940125687 antiparasitic agent Drugs 0.000 claims 1
- 239000002385 cottonseed oil Substances 0.000 claims 1
- 235000012343 cottonseed oil Nutrition 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 238000007918 intramuscular administration Methods 0.000 claims 1
- 238000007911 parenteral administration Methods 0.000 claims 1
- 239000000312 peanut oil Substances 0.000 claims 1
- 239000008188 pellet Substances 0.000 claims 1
- RNVYQYLELCKWAN-UHFFFAOYSA-N solketal Chemical compound CC1(C)OCC(CO)O1 RNVYQYLELCKWAN-UHFFFAOYSA-N 0.000 claims 1
- 238000010254 subcutaneous injection Methods 0.000 claims 1
- 239000007929 subcutaneous injection Substances 0.000 claims 1
- 235000015112 vegetable and seed oil Nutrition 0.000 claims 1
- 239000008158 vegetable oil Substances 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 241000238631 Hexapoda Species 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000031709 bromination Effects 0.000 description 4
- 238000005893 bromination reaction Methods 0.000 description 4
- 210000001035 gastrointestinal tract Anatomy 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
- 239000002904 solvent Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 210000001519 tissue Anatomy 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 3
- 208000006968 Helminthiasis Diseases 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000244206 Nematoda Species 0.000 description 3
- 241000607479 Yersinia pestis Species 0.000 description 3
- 125000000746 allylic group Chemical group 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 244000000013 helminth Species 0.000 description 3
- 210000000056 organ Anatomy 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 241000238876 Acari Species 0.000 description 2
- 241001147657 Ancylostoma Species 0.000 description 2
- 241000238421 Arthropoda Species 0.000 description 2
- 241000244186 Ascaris Species 0.000 description 2
- 241000283690 Bos taurus Species 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- 241000253350 Capillaria Species 0.000 description 2
- 241001126268 Cooperia Species 0.000 description 2
- 241000283086 Equidae Species 0.000 description 2
- 241000243976 Haemonchus Species 0.000 description 2
- 241001137882 Nematodirus Species 0.000 description 2
- 241000510960 Oesophagostomum Species 0.000 description 2
- 241001494479 Pecora Species 0.000 description 2
- 241000283984 Rodentia Species 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 241000244174 Strongyloides Species 0.000 description 2
- 241000243774 Trichinella Species 0.000 description 2
- 241001489151 Trichuris Species 0.000 description 2
- 230000000507 anthelmentic effect Effects 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000000855 fermentation Methods 0.000 description 2
- 230000004151 fermentation Effects 0.000 description 2
- 230000000968 intestinal effect Effects 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 208000014837 parasitic helminthiasis infectious disease Diseases 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 241000396431 Anthrenus scrophulariae Species 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 241000204727 Ascaridia Species 0.000 description 1
- 241000760149 Aspiculuris Species 0.000 description 1
- 241000131286 Attagenus Species 0.000 description 1
- 241000238658 Blattella Species 0.000 description 1
- 241001674044 Blattodea Species 0.000 description 1
- 241000244036 Brugia Species 0.000 description 1
- 241000931178 Bunostomum Species 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- 241000893172 Chabertia Species 0.000 description 1
- 241000692095 Cuterebra Species 0.000 description 1
- 241001147667 Dictyocaulus Species 0.000 description 1
- 241000243990 Dirofilaria Species 0.000 description 1
- 235000003550 Dracunculus Nutrition 0.000 description 1
- 241000316827 Dracunculus <angiosperm> Species 0.000 description 1
- 241000498256 Enterobius Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 241001660203 Gasterophilus Species 0.000 description 1
- 241000920462 Heterakis Species 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 241000257176 Hypoderma <fly> Species 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241000257162 Lucilia <blowfly> Species 0.000 description 1
- 241000920471 Lucilia caesar Species 0.000 description 1
- 208000002720 Malnutrition Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241001143352 Meloidogyne Species 0.000 description 1
- YZBLFMPOMVTDJY-LSGXYNIPSA-N Moxidectin Chemical compound O1[C@H](C(\C)=C\C(C)C)[C@@H](C)C(=N/OC)/C[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 YZBLFMPOMVTDJY-LSGXYNIPSA-N 0.000 description 1
- 241000257159 Musca domestica Species 0.000 description 1
- 241000498271 Necator Species 0.000 description 1
- 241000243981 Onchocerca Species 0.000 description 1
- 241000238814 Orthoptera Species 0.000 description 1
- 241000243795 Ostertagia Species 0.000 description 1
- 241000904715 Oxyuris Species 0.000 description 1
- 241000244187 Parascaris Species 0.000 description 1
- 241001674048 Phthiraptera Species 0.000 description 1
- 241000258242 Siphonaptera Species 0.000 description 1
- 241000187747 Streptomyces Species 0.000 description 1
- 241000122932 Strongylus Species 0.000 description 1
- 241000282898 Sus scrofa Species 0.000 description 1
- 241000975704 Syphacia Species 0.000 description 1
- 241000254105 Tenebrio Species 0.000 description 1
- 241001454295 Tetranychidae Species 0.000 description 1
- 241001454294 Tetranychus Species 0.000 description 1
- 241000333689 Tineola Species 0.000 description 1
- 241000607216 Toxascaris Species 0.000 description 1
- 241000244031 Toxocara Species 0.000 description 1
- 241000254086 Tribolium <beetle> Species 0.000 description 1
- 241000243797 Trichostrongylus Species 0.000 description 1
- 241000571986 Uncinaria Species 0.000 description 1
- 229920001938 Vegetable gum Polymers 0.000 description 1
- 241000244002 Wuchereria Species 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- 239000000921 anthelmintic agent Substances 0.000 description 1
- 229940124339 anthelmintic agent Drugs 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 244000078703 ectoparasite Species 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 208000035474 group of disease Diseases 0.000 description 1
- 210000002216 heart Anatomy 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 210000003563 lymphoid tissue Anatomy 0.000 description 1
- 230000001071 malnutrition Effects 0.000 description 1
- 235000000824 malnutrition Nutrition 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 230000001617 migratory effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 208000015380 nutritional deficiency disease Diseases 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 230000009528 severe injury Effects 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007892 solid unit dosage form Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 210000004304 subcutaneous tissue Anatomy 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- 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
- A61P33/10—Anthelmintics
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/786,172 US4093629A (en) | 1977-04-11 | 1977-04-11 | Derivatives of antibiotic substance milbemycin and processes therefor |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ186852A true NZ186852A (en) | 1984-09-28 |
Family
ID=25137800
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ186852A NZ186852A (en) | 1977-04-11 | 1978-04-03 | 13-hydroxy,-bromo,and-acetoxy-milbemycins and parasiticidal compositions |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4093629A (2) |
| JP (1) | JPS53130695A (2) |
| AU (1) | AU516707B2 (2) |
| FR (1) | FR2387232A1 (2) |
| GB (1) | GB1576185A (2) |
| NZ (1) | NZ186852A (2) |
| ZA (1) | ZA782023B (2) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6214367B1 (en) | 1996-06-05 | 2001-04-10 | Ashmont Holdings Limited | Injectable compositions |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4206205A (en) * | 1977-10-03 | 1980-06-03 | Merck & Co., Inc. | Monosaccharide and aglycone derivatives of C-076 |
| US4201861A (en) * | 1977-10-03 | 1980-05-06 | Merck & Co., Inc. | Acyl derivatives of C-076 compounds |
| IL56149A (en) * | 1977-12-19 | 1989-09-28 | Merck & Co Inc | 13-halo and 13-deoxy derivatives of c-076 compounds,their preparation and method for the treatment of parasitic infections in animals therewith |
| US4203976A (en) * | 1978-08-02 | 1980-05-20 | Merck & Co., Inc. | Sugar derivatives of C-076 compounds |
| US4200581A (en) * | 1978-08-04 | 1980-04-29 | Merck & Co., Inc. | Alkyl 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 |
| US4389397A (en) * | 1980-08-04 | 1983-06-21 | Merck & Co., Inc. | Solubilization of ivermectin in water |
| US4285963A (en) * | 1980-08-07 | 1981-08-25 | Merck & Co., Inc. | Novel derivatives of C-076 compounds |
| US4378353A (en) * | 1981-02-17 | 1983-03-29 | Merck & Co., Inc. | Novel C-076 compounds |
| US4408059A (en) * | 1981-12-04 | 1983-10-04 | University Patents, Inc. | Spiroketals useful as intermediates in the synthesis of milbemycin and avermectin macrolides |
| 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 |
| US4469682A (en) * | 1983-01-28 | 1984-09-04 | Merck & Co., Inc. | Avermectin and milbemycin phosphate esters, pharmaceutical compositions, and method of use |
| US4579864A (en) * | 1984-06-11 | 1986-04-01 | Merck & Co., Inc. | Avermectin and milbemycin 13-keto, 13-imino and 13-amino derivatives |
| EP0180539A1 (de) * | 1984-09-18 | 1986-05-07 | Ciba-Geigy Ag | 13-Halo- und 13-Hydroximilbemycine |
| AU574852B2 (en) * | 1984-10-26 | 1988-07-14 | Sankyo Company Limited | 13 - acyloxy - 5 - ketomilbemycin derivatives and preparation of 13 - hydroxy - 5 - ketomilbemycin derivatives |
| GB2168345B (en) * | 1984-12-14 | 1988-05-25 | Ciba Geigy Ag | Pesticidal 13b-substituted milbemycin derivatives |
| FI860233L (fi) * | 1985-01-22 | 1986-07-23 | Ciba Geigy Ag | 13 -alkyl-milbemycinderivat foer bekaempning av parasiter hos djur och vaexter. |
| US4587247A (en) * | 1985-02-25 | 1986-05-06 | Merck & Co., Inc. | Substituted and unsubstituted 13-(alkoxy)methoxy derivatives of the avermectin aglycones, compositions and use |
| US4666937A (en) * | 1985-03-04 | 1987-05-19 | Merck & Co., Inc. | Avermectin bioconversion products |
| 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 |
| US4812582A (en) * | 1985-07-22 | 1989-03-14 | The Upjohn Company | Process for preparing aldol intermediates |
| US4814347A (en) * | 1985-07-22 | 1989-03-21 | The Upjohn Company | Anthelmintic spiroketals and method of use |
| US4680419A (en) * | 1985-07-22 | 1987-07-14 | The Upjohn Company | Spiroketals and process for preparing same |
| US4686297A (en) * | 1985-07-22 | 1987-08-11 | The Upjohn Company | Anthelmintic spiroketals useful for killing parasitic worms |
| US4820758A (en) * | 1985-07-22 | 1989-04-11 | The Upjohn Company | Novel [5.5]-spiroketals |
| DE3785936T2 (de) * | 1986-03-25 | 1993-08-26 | Sankyo Co | Makrolid-derivate, ihre herstellung und ihre verwendung. |
| ZA872140B (en) * | 1986-03-25 | 1988-11-30 | Sankyo Co | Microlide compounds,their preparation and their use |
| EP0252879B1 (de) * | 1986-07-02 | 1992-05-06 | Ciba-Geigy Ag | Pestizide |
| EP0254583B1 (en) * | 1986-07-24 | 1994-09-07 | Beecham Group Plc | Parasiticidal milbemycin derivatives, a process for their production, and compositions containing the same |
| US4897416A (en) * | 1987-02-18 | 1990-01-30 | Ciba-Geigy Corporation | Insecticides and parasiticides |
| EP0285561A3 (de) * | 1987-03-27 | 1989-10-25 | Ciba-Geigy Ag | Parasitizide und insektizide Milbemycin-Derivate |
| EP0325462A3 (en) * | 1988-01-22 | 1989-11-02 | Beecham Group Plc | Anthelmintic milbemycin derivatives |
| US5008250A (en) * | 1988-05-25 | 1991-04-16 | Merck & Co., Inc. | Avermectins with a cleaved furan ring and an 8a hydroxy group |
| AU9785698A (en) | 1997-10-02 | 1999-04-27 | Microcide Pharmaceuticals, Inc. | Fungal efflux pump inhibitors |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4914624A (2) * | 1972-06-08 | 1974-02-08 | ||
| US3984564A (en) * | 1972-06-08 | 1976-10-05 | Sankyo Company Limited | Antibiotic substances B-41, their production and their use as insecticides and acaricides |
| US3950360A (en) * | 1972-06-08 | 1976-04-13 | Sankyo Company Limited | Antibiotic substances |
| SE434277B (sv) * | 1976-04-19 | 1984-07-16 | Merck & Co Inc | Sett att framstella nya antihelmintiskt verkande foreningar genom odling av streptomyces avermitilis |
-
1977
- 1977-04-11 US US05/786,172 patent/US4093629A/en not_active Expired - Lifetime
-
1978
- 1978-04-03 NZ NZ186852A patent/NZ186852A/en unknown
- 1978-04-04 AU AU34761/78A patent/AU516707B2/en not_active Expired
- 1978-04-06 FR FR7810240A patent/FR2387232A1/fr active Granted
- 1978-04-06 GB GB13531/78A patent/GB1576185A/en not_active Expired
- 1978-04-10 ZA ZA00782023A patent/ZA782023B/xx unknown
- 1978-04-11 JP JP4183478A patent/JPS53130695A/ja active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6214367B1 (en) | 1996-06-05 | 2001-04-10 | Ashmont Holdings Limited | Injectable compositions |
| US6663879B2 (en) | 1996-06-05 | 2003-12-16 | Ashmont Holdings Limited | Injectable compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| AU3476178A (en) | 1979-10-11 |
| AU516707B2 (en) | 1981-06-18 |
| GB1576185A (en) | 1980-10-01 |
| ZA782023B (en) | 1979-07-25 |
| FR2387232A1 (fr) | 1978-11-10 |
| US4093629A (en) | 1978-06-06 |
| JPS53130695A (en) | 1978-11-14 |
| FR2387232B1 (2) | 1982-04-09 |
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