CA1160169A - Derivatives of c-076 compounds - Google Patents
Derivatives of c-076 compoundsInfo
- Publication number
- CA1160169A CA1160169A CA000383192A CA383192A CA1160169A CA 1160169 A CA1160169 A CA 1160169A CA 000383192 A CA000383192 A CA 000383192A CA 383192 A CA383192 A CA 383192A CA 1160169 A CA1160169 A CA 1160169A
- Authority
- CA
- Canada
- Prior art keywords
- compounds
- sec
- butyl
- liters
- derivative
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 title abstract description 70
- 238000000034 method Methods 0.000 claims abstract description 22
- 239000000203 mixture Substances 0.000 claims abstract description 21
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 235000015097 nutrients Nutrition 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 4
- 230000000875 corresponding effect Effects 0.000 claims 2
- 241000187747 Streptomyces Species 0.000 claims 1
- 238000000855 fermentation Methods 0.000 abstract description 17
- 230000004151 fermentation Effects 0.000 abstract description 17
- 239000003096 antiparasitic agent Substances 0.000 abstract description 7
- 229940125687 antiparasitic agent Drugs 0.000 abstract description 5
- 125000004122 cyclic group Chemical group 0.000 abstract description 2
- 230000003389 potentiating effect Effects 0.000 abstract description 2
- 230000004071 biological effect Effects 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 241001465754 Metazoa Species 0.000 description 21
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 13
- 244000045947 parasite Species 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 235000010633 broth Nutrition 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000011282 treatment Methods 0.000 description 6
- 241000238631 Hexapoda Species 0.000 description 5
- 208000030852 Parasitic disease Diseases 0.000 description 5
- 241001468227 Streptomyces avermitilis Species 0.000 description 5
- 241000607479 Yersinia pestis Species 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 238000002955 isolation Methods 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 241000238876 Acari Species 0.000 description 4
- 208000006968 Helminthiasis Diseases 0.000 description 4
- 241000282414 Homo sapiens Species 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000013019 agitation Methods 0.000 description 4
- 230000002141 anti-parasite Effects 0.000 description 4
- 238000010828 elution Methods 0.000 description 4
- 239000012065 filter cake Substances 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
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 210000001519 tissue Anatomy 0.000 description 4
- 239000003981 vehicle Substances 0.000 description 4
- 241000238421 Arthropoda Species 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 241000244206 Nematoda Species 0.000 description 3
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 3
- 230000000507 anthelmentic effect Effects 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 244000000013 helminth Species 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 235000012054 meals Nutrition 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 210000000056 organ Anatomy 0.000 description 3
- 208000014837 parasitic helminthiasis infectious disease Diseases 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- -1 sec-butyl -OCH3 Chemical class 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 230000001954 sterilising effect Effects 0.000 description 3
- 238000004659 sterilization and disinfection Methods 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- 241001147657 Ancylostoma 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
- 241001126268 Cooperia Species 0.000 description 2
- 241001147667 Dictyocaulus Species 0.000 description 2
- 241000283086 Equidae Species 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 241000243976 Haemonchus Species 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 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
- 241001674048 Phthiraptera Species 0.000 description 2
- 241000283984 Rodentia Species 0.000 description 2
- 229920005654 Sephadex Polymers 0.000 description 2
- 239000012507 Sephadex™ Substances 0.000 description 2
- 241000258242 Siphonaptera Species 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
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 230000000895 acaricidal effect Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 125000000600 disaccharide group Chemical group 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000000968 intestinal effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 239000000401 methanolic extract Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000001069 nematicidal effect Effects 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- 244000144977 poultry Species 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000013589 supplement Substances 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
- 238000005406 washing Methods 0.000 description 2
- OWFJMIVZYSDULZ-PXOLEDIWSA-N (4s,4ar,5s,5ar,6s,12ar)-4-(dimethylamino)-1,5,6,10,11,12a-hexahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide Chemical compound C1=CC=C2[C@](O)(C)[C@H]3[C@H](O)[C@H]4[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]4(O)C(=O)C3=C(O)C2=C1O OWFJMIVZYSDULZ-PXOLEDIWSA-N 0.000 description 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- 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
- 241001674044 Blattodea Species 0.000 description 1
- 241000244036 Brugia Species 0.000 description 1
- 241000931178 Bunostomum Species 0.000 description 1
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 description 1
- 241000253350 Capillaria Species 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- 241000893172 Chabertia Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- 241000692095 Cuterebra 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
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 241000920462 Heterakis Species 0.000 description 1
- 241000257176 Hypoderma <fly> Species 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 235000019738 Limestone Nutrition 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
- 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
- 241000237502 Ostreidae Species 0.000 description 1
- 241000904715 Oxyuris Species 0.000 description 1
- 241000244187 Parascaris Species 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 208000035415 Reinfection Diseases 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
- 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
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 241000571986 Uncinaria Species 0.000 description 1
- 229920001938 Vegetable gum Polymers 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method 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
- 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
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 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
- 239000000969 carrier Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000008121 dextrose Substances 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
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 150000002016 disaccharides Chemical class 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 244000078703 ectoparasite Species 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000006052 feed supplement Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 208000035474 group of disease Diseases 0.000 description 1
- 210000002216 heart Anatomy 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 210000003563 lymphoid tissue Anatomy 0.000 description 1
- 239000003120 macrolide antibiotic agent Substances 0.000 description 1
- 229940041033 macrolides Drugs 0.000 description 1
- 230000001071 malnutrition Effects 0.000 description 1
- 235000000824 malnutrition Nutrition 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 230000001617 migratory effect Effects 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 230000003387 muscular Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 208000015380 nutritional deficiency disease Diseases 0.000 description 1
- 235000020636 oyster Nutrition 0.000 description 1
- 230000000590 parasiticidal effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 230000000717 retained effect Effects 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
- RNVYQYLELCKWAN-UHFFFAOYSA-N solketal Chemical compound CC1(C)OCC(CO)O1 RNVYQYLELCKWAN-UHFFFAOYSA-N 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
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- 210000002784 stomach Anatomy 0.000 description 1
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- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
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- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
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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
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/195—Antibiotics
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
- C12N1/20—Bacteria; Culture media therefor
- C12N1/205—Bacterial isolates
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/18—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms containing at least two hetero rings condensed among themselves or condensed with a common carbocyclic ring system, e.g. rifamycin
- C12P17/181—Heterocyclic compounds containing oxygen atoms as the only ring heteroatoms in the condensed system, e.g. Salinomycin, Septamycin
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/44—Preparation of O-glycosides, e.g. glucosides
- C12P19/60—Preparation of O-glycosides, e.g. glucosides having an oxygen of the saccharide radical directly bound to a non-saccharide heterocyclic ring or a condensed ring system containing a non-saccharide heterocyclic ring, e.g. coumermycin, novobiocin
- C12P19/62—Preparation of O-glycosides, e.g. glucosides having an oxygen of the saccharide radical directly bound to a non-saccharide heterocyclic ring or a condensed ring system containing a non-saccharide heterocyclic ring, e.g. coumermycin, novobiocin the hetero ring having eight or more ring members and only oxygen as ring hetero atoms, e.g. erythromycin, spiramycin, nystatin
- C12P19/623—Avermectin; Milbemycin; Ivermectin; C-076
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
- C12R2001/00—Microorganisms ; Processes using microorganisms
- C12R2001/01—Bacteria or Actinomycetales ; using bacteria or Actinomycetales
- C12R2001/465—Streptomyces
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Microbiology (AREA)
- General Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Molecular Biology (AREA)
- Food Science & Technology (AREA)
- Medicinal Chemistry (AREA)
- Tropical Medicine & Parasitology (AREA)
- Virology (AREA)
- Biomedical Technology (AREA)
- Animal Husbandry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Enzymes And Modification Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/175,615 US4285963A (en) | 1980-08-07 | 1980-08-07 | Novel derivatives of C-076 compounds |
| US175,615 | 1980-08-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1160169A true CA1160169A (en) | 1984-01-10 |
Family
ID=22640941
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000383192A Expired CA1160169A (en) | 1980-08-07 | 1981-08-04 | Derivatives of c-076 compounds |
Country Status (13)
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4429042A (en) | 1978-09-08 | 1984-01-31 | Merck & Co., Inc. | Strain of Streptomyces for producing antiparasitic compounds |
| US4378353A (en) * | 1981-02-17 | 1983-03-29 | Merck & Co., Inc. | Novel C-076 compounds |
| US4333925A (en) * | 1981-05-11 | 1982-06-08 | Merck & Co., Inc. | Derivatives of C-076 compounds |
| US4412991A (en) * | 1981-08-28 | 1983-11-01 | Merck & Co., Inc. | 22-Hydroxy derivatives of C-076 compounds, pharmaceutical compositions and method of use |
| US4423211A (en) * | 1981-12-21 | 1983-12-27 | Merck & Co., Inc. | Process for the whole broth extraction of avermectin |
| US5169956A (en) * | 1984-06-05 | 1992-12-08 | American Cyanamid Company | Macrolide antibiotic compounds |
| US5106994A (en) * | 1984-06-05 | 1992-04-21 | American Cyanamid Company | Agents and method of production thereof |
| US5317030A (en) * | 1984-06-05 | 1994-05-31 | American Cyanamid Company | Method and compositions for helmintic, arthropod ectoparasitic and acaridal infections with novel agents |
| US5198464A (en) * | 1984-06-05 | 1993-03-30 | American Cyanamid Company | Method and compositions for helmintic, arthropod ectoparasitic and acaridal infections with novel agents |
| EP0180539A1 (de) * | 1984-09-18 | 1986-05-07 | Ciba-Geigy Ag | 13-Halo- und 13-Hydroximilbemycine |
| GB2168345B (en) * | 1984-12-14 | 1988-05-25 | Ciba Geigy Ag | Pesticidal 13b-substituted milbemycin derivatives |
| ES8800986A1 (es) * | 1985-07-27 | 1987-12-01 | Pfizer | Un procedimiento para la produccion de un nuevo derivado de avermectina |
| US5840704A (en) * | 1986-07-16 | 1998-11-24 | Pfizer Inc. | Antiparasitic agents and process for their preparation |
| US5238848A (en) * | 1987-01-23 | 1993-08-24 | Pfizer Inc | Cultures for production of avermectins |
| US5525506A (en) * | 1987-01-23 | 1996-06-11 | Pfizer Inc. | Process for production of avermectins and cultures therefor |
| US5234831A (en) * | 1987-01-23 | 1993-08-10 | Pfizer Inc | Cultures for production of B avermectins |
| US5240850A (en) * | 1987-10-23 | 1993-08-31 | Pfizer Inc. | Cultures for production of avermectin aglycones |
| EP0319142B1 (en) * | 1987-11-03 | 1994-04-06 | Beecham Group Plc | Intermediates for the preparation of anthelmintic macrolide antibiotics |
| ATE87926T1 (de) * | 1987-11-09 | 1993-04-15 | Pfizer | Ethylierte avermectine. |
| GB8726730D0 (en) * | 1987-11-14 | 1987-12-16 | Pfizer Ltd | Antiparasitic agents |
| US5008250A (en) * | 1988-05-25 | 1991-04-16 | Merck & Co., Inc. | Avermectins with a cleaved furan ring and an 8a hydroxy group |
| US5188944A (en) * | 1990-06-22 | 1993-02-23 | Merck & Co., Inc. | Process for the glycosylation of avermectin agylcones |
| US6103504A (en) * | 1992-03-25 | 2000-08-15 | Pfizer Inc. | Process for production of avermectins and cultures therefor |
| GB9226525D0 (en) * | 1992-12-19 | 1993-02-10 | Pfizer Ltd | Antiparasitic agents |
| MX2012006921A (es) | 2009-12-17 | 2012-07-10 | Merial Ltd | Composiciones que comprenden compuestos de lactona macrociclica y espirodioxepinoindoles. |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3998699A (en) * | 1972-06-08 | 1976-12-21 | 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 |
| US4093629A (en) * | 1977-04-11 | 1978-06-06 | Merck & Co., Inc. | Derivatives of antibiotic substance milbemycin and processes therefor |
| NZ188459A (en) * | 1977-10-03 | 1982-09-07 | Merck & Co Inc | Derivatives of c-076 compounds and pesticidal compositions |
| US4172940A (en) * | 1977-10-03 | 1979-10-30 | Merck & Co., Inc. | Purification of C-076 compounds by single column chromatography |
| PH15982A (en) * | 1977-10-03 | 1983-05-18 | Merck & Co Inc | Selective hydrogenation producta of c-076 compounds and derivatives thereof |
| US4161583A (en) * | 1977-10-03 | 1979-07-17 | Merck & Co., Inc. | Method for the separation and purification of antibiotic macrolides |
| 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 |
| US4200581A (en) * | 1978-08-04 | 1980-04-29 | Merck & Co., Inc. | Alkyl derivatives of C-076 compounds |
-
1980
- 1980-08-07 US US06/175,615 patent/US4285963A/en not_active Expired - Lifetime
-
1981
- 1981-07-27 NZ NZ197860A patent/NZ197860A/en unknown
- 1981-07-31 GR GR65691A patent/GR74278B/el unknown
- 1981-08-03 AT AT81303543T patent/ATE4167T1/de not_active IP Right Cessation
- 1981-08-03 DE DE8181303543T patent/DE3160652D1/de not_active Expired
- 1981-08-03 EP EP81303543A patent/EP0046045B1/en not_active Expired
- 1981-08-03 PT PT73470A patent/PT73470B/pt unknown
- 1981-08-04 CA CA000383192A patent/CA1160169A/en not_active Expired
- 1981-08-05 AU AU73820/81A patent/AU541097B2/en not_active Ceased
- 1981-08-05 ES ES504576A patent/ES504576A0/es active Granted
- 1981-08-06 ZA ZA815406A patent/ZA815406B/xx unknown
- 1981-08-06 DK DK349581A patent/DK349581A/da not_active Application Discontinuation
- 1981-08-07 JP JP56123170A patent/JPS5759892A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP0046045B1 (en) | 1983-07-20 |
| ES8302092A1 (es) | 1983-01-01 |
| US4285963A (en) | 1981-08-25 |
| AU541097B2 (en) | 1984-12-13 |
| GR74278B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-06-21 |
| EP0046045A1 (en) | 1982-02-17 |
| DE3160652D1 (en) | 1983-08-25 |
| DK349581A (da) | 1982-02-08 |
| NZ197860A (en) | 1985-02-28 |
| AU7382081A (en) | 1982-02-11 |
| ES504576A0 (es) | 1983-01-01 |
| PT73470A (en) | 1981-09-01 |
| ZA815406B (en) | 1983-03-30 |
| PT73470B (en) | 1983-09-01 |
| JPS5759892A (en) | 1982-04-10 |
| ATE4167T1 (de) | 1983-08-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |