RU1806198C - Способ получени авермектина В - Google Patents
Способ получени авермектина ВInfo
- Publication number
- RU1806198C RU1806198C SU884355079A SU4355079A RU1806198C RU 1806198 C RU1806198 C RU 1806198C SU 884355079 A SU884355079 A SU 884355079A SU 4355079 A SU4355079 A SU 4355079A RU 1806198 C RU1806198 C RU 1806198C
- Authority
- RU
- Russia
- Prior art keywords
- acid
- cyclopentyl
- retention time
- alpha
- minutes
- Prior art date
Links
- 239000005660 Abamectin Substances 0.000 title claims abstract description 13
- 238000000034 method Methods 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title abstract description 3
- RRZXIRBKKLTSOM-XPNPUAGNSA-N avermectin B1a Chemical compound 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 title description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 3
- 238000012258 culturing Methods 0.000 claims abstract 2
- 230000014759 maintenance of location Effects 0.000 claims description 10
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 8
- MNULEGDCPYONBU-UIXCWHRQSA-N (1R,4E,5'S,6S,6'S,7R,8S,10R,11R,12S,14R,15S,16R,18Z,20Z,22R,25S,27R,28S,29R)-22-ethyl-7,11,14,15-tetrahydroxy-6'-[(2R)-2-hydroxypropyl]-5',6,8,10,12,14,16,28,29-nonamethylspiro[2,26-dioxabicyclo[23.3.1]nonacosa-4,18,20-triene-27,2'-oxane]-3,9,13-trione Polymers CC[C@@H]1CC[C@@H]2O[C@]3(CC[C@H](C)[C@H](C[C@@H](C)O)O3)[C@@H](C)[C@H](OC(=O)\C=C\[C@H](C)[C@@H](O)[C@H](C)C(=O)[C@H](C)[C@@H](O)[C@H](C)C(=O)[C@](C)(O)[C@@H](O)[C@H](C)C\C=C/C=C\1)[C@@H]2C MNULEGDCPYONBU-UIXCWHRQSA-N 0.000 claims description 6
- MNULEGDCPYONBU-CBLVMMTCSA-N (1R,4Z,5'S,6S,6'S,7R,8S,10R,11R,12S,14R,15S,16R,18Z,20Z,22R,25S,27R,28S,29R)-22-ethyl-7,11,14,15-tetrahydroxy-6'-[(2R)-2-hydroxypropyl]-5',6,8,10,12,14,16,28,29-nonamethylspiro[2,26-dioxabicyclo[23.3.1]nonacosa-4,18,20-triene-27,2'-oxane]-3,9,13-trione Polymers CC[C@@H]1CC[C@@H]2O[C@]3(CC[C@H](C)[C@H](C[C@@H](C)O)O3)[C@@H](C)[C@H](OC(=O)\C=C/[C@H](C)[C@@H](O)[C@H](C)C(=O)[C@H](C)[C@@H](O)[C@H](C)C(=O)[C@](C)(O)[C@@H](O)[C@H](C)C\C=C/C=C\1)[C@@H]2C MNULEGDCPYONBU-CBLVMMTCSA-N 0.000 claims description 6
- MNULEGDCPYONBU-WABYXMGOSA-N (1S,4E,5'R,6R,6'R,7S,8R,10S,11S,12R,14S,15R,16S,18E,22S,25R,27S,28R,29S)-22-ethyl-7,11,14,15-tetrahydroxy-6'-(2-hydroxypropyl)-5',6,8,10,12,14,16,28,29-nonamethylspiro[2,26-dioxabicyclo[23.3.1]nonacosa-4,18,20-triene-27,2'-oxane]-3,9,13-trione Polymers CC[C@H]1CC[C@H]2O[C@@]3(CC[C@@H](C)[C@@H](CC(C)O)O3)[C@H](C)[C@@H](OC(=O)\C=C\[C@@H](C)[C@H](O)[C@@H](C)C(=O)[C@@H](C)[C@H](O)[C@@H](C)C(=O)[C@@](C)(O)[C@H](O)[C@@H](C)C\C=C\C=C1)[C@H]2C MNULEGDCPYONBU-WABYXMGOSA-N 0.000 claims description 6
- MNULEGDCPYONBU-QECWTJOCSA-N (1r,4s,5e,5'r,6'r,7e,10s,11r,12s,14r,15s,16s,18r,19s,20r,21e,25s,26r,27s,29s)-4-ethyl-11,12,15,19-tetrahydroxy-6'-(2-hydroxypropyl)-5',10,12,14,16,18,20,26,29-nonamethylspiro[24,28-dioxabicyclo[23.3.1]nonacosa-5,7,21-triene-27,2'-oxane]-13,17,23-trione Polymers O([C@@H]1CC[C@@H](/C=C/C=C/C[C@H](C)[C@@H](O)[C@](C)(O)C(=O)[C@H](C)[C@@H](O)[C@H](C)C(=O)[C@H](C)[C@@H](O)[C@H](C)/C=C/C(=O)O[C@H]([C@H]2C)[C@H]1C)CC)[C@]12CC[C@@H](C)[C@@H](CC(C)O)O1 MNULEGDCPYONBU-QECWTJOCSA-N 0.000 claims description 6
- MNULEGDCPYONBU-WMBHJXFZSA-N (1r,4s,5e,5'r,6'r,7e,10s,11r,12s,14r,15s,16s,18r,19s,20r,21e,25s,26r,27s,29s)-4-ethyl-11,12,15,19-tetrahydroxy-6'-[(2s)-2-hydroxypropyl]-5',10,12,14,16,18,20,26,29-nonamethylspiro[24,28-dioxabicyclo[23.3.1]nonacosa-5,7,21-triene-27,2'-oxane]-13,17,23-trio Polymers O([C@@H]1CC[C@@H](/C=C/C=C/C[C@H](C)[C@@H](O)[C@](C)(O)C(=O)[C@H](C)[C@@H](O)[C@H](C)C(=O)[C@H](C)[C@@H](O)[C@H](C)/C=C/C(=O)O[C@H]([C@H]2C)[C@H]1C)CC)[C@]12CC[C@@H](C)[C@@H](C[C@H](C)O)O1 MNULEGDCPYONBU-WMBHJXFZSA-N 0.000 claims description 6
- MNULEGDCPYONBU-BOXGPLBDSA-N (1r,4s,5e,5'r,6'r,7e,10s,11s,12s,14r,15s,16s,18r,19s,20r,21e,25s,26r,27s,29s)-4-ethyl-11,12,15,19-tetrahydroxy-6'-[(2s)-2-hydroxypropyl]-5',10,12,14,16,18,20,26,29-nonamethylspiro[24,28-dioxabicyclo[23.3.1]nonacosa-5,7,21-triene-27,2'-oxane]-13,17,23-trio Polymers O([C@@H]1CC[C@@H](/C=C/C=C/C[C@H](C)[C@H](O)[C@](C)(O)C(=O)[C@H](C)[C@@H](O)[C@H](C)C(=O)[C@H](C)[C@@H](O)[C@H](C)/C=C/C(=O)O[C@H]([C@H]2C)[C@H]1C)CC)[C@]12CC[C@@H](C)[C@@H](C[C@H](C)O)O1 MNULEGDCPYONBU-BOXGPLBDSA-N 0.000 claims description 6
- MNULEGDCPYONBU-YOKYSHDFSA-N (5'R,10S,11R,12S,14S,15R,16R,18R,19S,20R,26R,29S)-4-ethyl-11,12,15,19-tetrahydroxy-6'-[(2S)-2-hydroxypropyl]-5',10,12,14,16,18,20,26,29-nonamethylspiro[24,28-dioxabicyclo[23.3.1]nonacosa-5,7,21-triene-27,2'-oxane]-13,17,23-trione Polymers C([C@H](C)[C@@H](O)[C@](C)(O)C(=O)[C@@H](C)[C@H](O)[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@H](C)C=CC(=O)OC([C@H]1C)[C@H]2C)C=CC=CC(CC)CCC2OC21CC[C@@H](C)C(C[C@H](C)O)O2 MNULEGDCPYONBU-YOKYSHDFSA-N 0.000 claims description 6
- MNULEGDCPYONBU-VVXVDZGXSA-N (5e,5'r,7e,10s,11r,12s,14s,15r,16r,18r,19s,20r,21e,26r,29s)-4-ethyl-11,12,15,19-tetrahydroxy-6'-[(2s)-2-hydroxypropyl]-5',10,12,14,16,18,20,26,29-nonamethylspiro[24,28-dioxabicyclo[23.3.1]nonacosa-5,7,21-triene-27,2'-oxane]-13,17,23-trione Polymers C([C@H](C)[C@@H](O)[C@](C)(O)C(=O)[C@@H](C)[C@H](O)[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@H](C)/C=C/C(=O)OC([C@H]1C)[C@H]2C)\C=C\C=C\C(CC)CCC2OC21CC[C@@H](C)C(C[C@H](C)O)O2 MNULEGDCPYONBU-VVXVDZGXSA-N 0.000 claims description 6
- MNULEGDCPYONBU-MQLHLVDXSA-N CC[C@@H]1CC[C@@H]2O[C@]3(CC[C@H](C)[C@H](C[C@@H](C)O)O3)[C@@H](C)[C@H](OC(=O)\C=C\[C@H](C)[C@@H](O)[C@H](C)C(=O)[C@H](C)[C@@H](O)[C@H](C)C(=O)[C@](C)(O)[C@@H](O)[C@H](C)C\C=C\C=C\1)C2C Polymers CC[C@@H]1CC[C@@H]2O[C@]3(CC[C@H](C)[C@H](C[C@@H](C)O)O3)[C@@H](C)[C@H](OC(=O)\C=C\[C@H](C)[C@@H](O)[C@H](C)C(=O)[C@H](C)[C@@H](O)[C@H](C)C(=O)[C@](C)(O)[C@@H](O)[C@H](C)C\C=C\C=C\1)C2C MNULEGDCPYONBU-MQLHLVDXSA-N 0.000 claims description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- MNULEGDCPYONBU-AWJDAWNUSA-N oligomycin A Polymers O([C@H]1CC[C@H](/C=C/C=C/C[C@@H](C)[C@H](O)[C@@](C)(O)C(=O)[C@@H](C)[C@H](O)[C@@H](C)C(=O)[C@@H](C)[C@H](O)[C@@H](C)/C=C/C(=O)O[C@@H]([C@@H]2C)[C@@H]1C)CC)[C@@]12CC[C@H](C)[C@H](C[C@@H](C)O)O1 MNULEGDCPYONBU-AWJDAWNUSA-N 0.000 claims description 6
- MNULEGDCPYONBU-UHFFFAOYSA-N oligomycin A Natural products CC1C(C2C)OC(=O)C=CC(C)C(O)C(C)C(=O)C(C)C(O)C(C)C(=O)C(C)(O)C(O)C(C)CC=CC=CC(CC)CCC2OC21CCC(C)C(CC(C)O)O2 MNULEGDCPYONBU-UHFFFAOYSA-N 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 229920002472 Starch Polymers 0.000 claims description 3
- 235000010216 calcium carbonate Nutrition 0.000 claims description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000008107 starch Substances 0.000 claims description 3
- 235000019698 starch Nutrition 0.000 claims description 3
- 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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 239000002609 medium Substances 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 241000193830 Bacillus <bacterium> Species 0.000 claims 1
- 229920002245 Dextrose equivalent Polymers 0.000 claims 1
- 241000187747 Streptomyces Species 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 102000004139 alpha-Amylases Human genes 0.000 claims 1
- 108090000637 alpha-Amylases Proteins 0.000 claims 1
- 229940024171 alpha-amylase Drugs 0.000 claims 1
- 239000012736 aqueous medium Substances 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 102000004169 proteins and genes Human genes 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 235000015097 nutrients Nutrition 0.000 abstract description 2
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 230000002141 anti-parasite Effects 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 230000002906 microbiologic effect Effects 0.000 abstract 1
- 238000001228 spectrum Methods 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 238000000855 fermentation Methods 0.000 description 9
- 230000004151 fermentation Effects 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 229920001817 Agar Polymers 0.000 description 8
- 239000008272 agar Substances 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 229910003002 lithium salt Inorganic materials 0.000 description 3
- 159000000002 lithium salts Chemical class 0.000 description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 235000011148 calcium chloride Nutrition 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 235000013619 trace mineral Nutrition 0.000 description 2
- 239000011573 trace mineral Substances 0.000 description 2
- OVBFMEVBMNZIBR-RXMQYKEDSA-N (2r)-2-methylpentanoic acid Chemical compound CCC[C@@H](C)C(O)=O OVBFMEVBMNZIBR-RXMQYKEDSA-N 0.000 description 1
- OVBFMEVBMNZIBR-UHFFFAOYSA-N -2-Methylpentanoic acid Natural products CCCC(C)C(O)=O OVBFMEVBMNZIBR-UHFFFAOYSA-N 0.000 description 1
- XLUXAKJPHJEFKL-UHFFFAOYSA-N 1-ethylcyclobutane-1-carboxylic acid Chemical compound CCC1(C(O)=O)CCC1 XLUXAKJPHJEFKL-UHFFFAOYSA-N 0.000 description 1
- HVRZYSHVZOELOH-UHFFFAOYSA-N 2-Methyl-4-pentenoic acid Chemical compound OC(=O)C(C)CC=C HVRZYSHVZOELOH-UHFFFAOYSA-N 0.000 description 1
- AMOJMSPUYHSMKI-UHFFFAOYSA-N 2-cyclopropylpropanoic acid Chemical compound OC(=O)C(C)C1CC1 AMOJMSPUYHSMKI-UHFFFAOYSA-N 0.000 description 1
- WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 description 1
- AYEGPMGNMOIHDL-UHFFFAOYSA-N 2-methylcyclopropane-1-carboxylic acid Chemical compound CC1CC1C(O)=O AYEGPMGNMOIHDL-UHFFFAOYSA-N 0.000 description 1
- CVKMFSAVYPAZTQ-UHFFFAOYSA-N 2-methylhexanoic acid Chemical compound CCCCC(C)C(O)=O CVKMFSAVYPAZTQ-UHFFFAOYSA-N 0.000 description 1
- IUBCTUXJYXUSAZ-UHFFFAOYSA-N 2-methylpentanethioic s-acid Chemical compound CCCC(C)C(S)=O IUBCTUXJYXUSAZ-UHFFFAOYSA-N 0.000 description 1
- WTLKTXIHIHFSGU-UHFFFAOYSA-N 2-nitrosoguanidine Chemical compound NC(N)=NN=O WTLKTXIHIHFSGU-UHFFFAOYSA-N 0.000 description 1
- IBMXMCXCSPGCDQ-UHFFFAOYSA-N 3-cyclopentylpropan-1-ol Chemical compound OCCCC1CCCC1 IBMXMCXCSPGCDQ-UHFFFAOYSA-N 0.000 description 1
- ZRPLANDPDWYOMZ-UHFFFAOYSA-N 3-cyclopentylpropionic acid Chemical compound OC(=O)CCC1CCCC1 ZRPLANDPDWYOMZ-UHFFFAOYSA-N 0.000 description 1
- LQXHCYIDZUPZNK-UHFFFAOYSA-N 3-fluorocyclobutane-1-carboxylic acid Chemical compound OC(=O)C1CC(F)C1 LQXHCYIDZUPZNK-UHFFFAOYSA-N 0.000 description 1
- RBIGKSZIQCTIJF-UHFFFAOYSA-N 3-formylthiophene Chemical compound O=CC=1C=CSC=1 RBIGKSZIQCTIJF-UHFFFAOYSA-N 0.000 description 1
- ZLXHOVJKNATDMT-UHFFFAOYSA-N 3-methylcyclobutane-1-carboxylic acid Chemical compound CC1CC(C(O)=O)C1 ZLXHOVJKNATDMT-UHFFFAOYSA-N 0.000 description 1
- CIFSKZDQGRCLBN-UHFFFAOYSA-N 3-methylcyclohexane-1-carboxylic acid Chemical compound CC1CCCC(C(O)=O)C1 CIFSKZDQGRCLBN-UHFFFAOYSA-N 0.000 description 1
- NNKLICLIBKMDOY-UHFFFAOYSA-N 3-methylidenecyclobutane-1-carboxylic acid Chemical compound OC(=O)C1CC(=C)C1 NNKLICLIBKMDOY-UHFFFAOYSA-N 0.000 description 1
- HYIUDFLDFSIXTR-UHFFFAOYSA-N 4,4-difluorocyclohexane-1-carboxylic acid Chemical compound OC(=O)C1CCC(F)(F)CC1 HYIUDFLDFSIXTR-UHFFFAOYSA-N 0.000 description 1
- AJZOYSGAEPJFKH-UHFFFAOYSA-N 4-methoxy-2-methylbutanoic acid Chemical compound COCCC(C)C(O)=O AJZOYSGAEPJFKH-UHFFFAOYSA-N 0.000 description 1
- DENSHBNKGSMOIU-UHFFFAOYSA-N 4-methylidenecyclohexane-1-carboxylic acid Chemical compound OC(=O)C1CCC(=C)CC1 DENSHBNKGSMOIU-UHFFFAOYSA-N 0.000 description 1
- POVPYUUZOZBLOH-UHFFFAOYSA-N 5-chlorothiophene-3-carboxylic acid Chemical compound OC(=O)C1=CSC(Cl)=C1 POVPYUUZOZBLOH-UHFFFAOYSA-N 0.000 description 1
- 240000007087 Apium graveolens Species 0.000 description 1
- 235000015849 Apium graveolens Dulce Group Nutrition 0.000 description 1
- 235000010591 Appio Nutrition 0.000 description 1
- JVGWUGTWQIAGHJ-DFAYUBCLSA-N Avermectin A2a Chemical compound C1[C@H](O)[C@H](C)[C@@H](C(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](OC)[C@H]3OC\2)O)C[C@H]4C1 JVGWUGTWQIAGHJ-DFAYUBCLSA-N 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 244000056139 Brassica cretica Species 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- 244000000626 Daucus carota Species 0.000 description 1
- 235000002767 Daucus carota Nutrition 0.000 description 1
- 101710088194 Dehydrogenase Proteins 0.000 description 1
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 description 1
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 1
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 1
- 240000008415 Lactuca sativa Species 0.000 description 1
- 235000003228 Lactuca sativa Nutrition 0.000 description 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 102000016397 Methyltransferase Human genes 0.000 description 1
- 108060004795 Methyltransferase Proteins 0.000 description 1
- 240000009164 Petroselinum crispum Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 244000300264 Spinacia oleracea Species 0.000 description 1
- 235000009337 Spinacia oleracea Nutrition 0.000 description 1
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 1
- 244000290333 Vanilla fragrans Species 0.000 description 1
- 235000009499 Vanilla fragrans Nutrition 0.000 description 1
- 235000012036 Vanilla tahitensis Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- JVGWUGTWQIAGHJ-UHFFFAOYSA-N avermectin A2a Natural products C1C(O)C(C)C(C(C)CC)OC11OC(CC=C(C)C(OC2OC(C)C(OC3OC(C)C(O)C(OC)C3)C(OC)C2)C(C)C=CC=C2C3(C(C(=O)O4)C=C(C)C(OC)C3OC2)O)CC4C1 JVGWUGTWQIAGHJ-UHFFFAOYSA-N 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- SIIVGPQREKVCOP-UHFFFAOYSA-N but-1-en-1-ol Chemical compound CCC=CO SIIVGPQREKVCOP-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- TXWOGHSRPAYOML-UHFFFAOYSA-N cyclobutanecarboxylic acid Chemical compound OC(=O)C1CCC1 TXWOGHSRPAYOML-UHFFFAOYSA-N 0.000 description 1
- LQNHRNOPWKZUSN-UHFFFAOYSA-N cyclobutylmethanamine Chemical compound NCC1CCC1 LQNHRNOPWKZUSN-UHFFFAOYSA-N 0.000 description 1
- WPOPOPFNZYPKAV-UHFFFAOYSA-N cyclobutylmethanol Chemical compound OCC1CCC1 WPOPOPFNZYPKAV-UHFFFAOYSA-N 0.000 description 1
- HJZLEGIHUQOJBA-UHFFFAOYSA-N cyclohexane propionic acid Chemical compound OC(=O)CCC1CCCCC1 HJZLEGIHUQOJBA-UHFFFAOYSA-N 0.000 description 1
- ADLKZHGHNJBOOC-UHFFFAOYSA-N cyclopent-3-en-1-ylmethanol Chemical compound OCC1CC=CC1 ADLKZHGHNJBOOC-UHFFFAOYSA-N 0.000 description 1
- PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 description 1
- ISQVBYGGNVVVHB-UHFFFAOYSA-N cyclopentylmethanol Chemical compound OCC1CCCC1 ISQVBYGGNVVVHB-UHFFFAOYSA-N 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- -1 ethyl 2- (3-thiophenecarbonyl) propionic acid Chemical compound 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- AVPKHOTUOHDTLW-UHFFFAOYSA-N oxane-4-carboxylic acid Chemical compound OC(=O)C1CCOCC1 AVPKHOTUOHDTLW-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 235000011197 perejil Nutrition 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- JSSXHAMIXJGYCS-UHFFFAOYSA-N piperazin-4-ium-2-carboxylate Chemical compound OC(=O)C1CNCCN1 JSSXHAMIXJGYCS-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000004237 preparative chromatography Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- BTYQWISIPUWRJR-UHFFFAOYSA-N tert-butyl 3-(2-methoxy-2-oxoethyl)piperidine-1-carboxylate Chemical compound COC(=O)CC1CCCN(C(=O)OC(C)(C)C)C1 BTYQWISIPUWRJR-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- SCKSQOIXSGPVJS-UHFFFAOYSA-N thiane-4-carboxylic acid Chemical compound OC(=O)C1CCSCC1 SCKSQOIXSGPVJS-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- BSNQHVPRAPQLSW-UHFFFAOYSA-N thiolane-3-carboxylic acid Chemical compound OC(=O)C1CCSC1 BSNQHVPRAPQLSW-UHFFFAOYSA-N 0.000 description 1
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 1
- YNVOMSDITJMNET-UHFFFAOYSA-N thiophene-3-carboxylic acid Chemical compound OC(=O)C=1C=CSC=1 YNVOMSDITJMNET-UHFFFAOYSA-N 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 235000015192 vegetable juice Nutrition 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 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
- 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
-
- 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
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
-
- 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Genetics & Genomics (AREA)
- Zoology (AREA)
- Biotechnology (AREA)
- Veterinary Medicine (AREA)
- Biochemistry (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Tropical Medicine & Parasitology (AREA)
- General Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Microbiology (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Virology (AREA)
- Biomedical Technology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Fodder In General (AREA)
- Steroid Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US651287A | 1987-01-23 | 1987-01-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU1806198C true RU1806198C (ru) | 1993-03-30 |
Family
ID=21721247
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU884355079A RU1806198C (ru) | 1987-01-23 | 1988-01-22 | Способ получени авермектина В |
Country Status (30)
| Country | Link |
|---|---|
| EP (2) | EP0276103B1 (Direct) |
| JP (2) | JPH0681757B2 (Direct) |
| KR (2) | KR900004419B1 (Direct) |
| CN (1) | CN1056883C (Direct) |
| AR (1) | AR241798A1 (Direct) |
| AT (2) | ATE96174T1 (Direct) |
| AU (2) | AU595673B2 (Direct) |
| BG (1) | BG51051A3 (Direct) |
| BR (1) | BR8800271A (Direct) |
| CZ (1) | CZ279782B6 (Direct) |
| DD (2) | DD267512A5 (Direct) |
| DE (2) | DE3884973T2 (Direct) |
| DK (2) | DK28988A (Direct) |
| EG (1) | EG18797A (Direct) |
| ES (2) | ES2059498T3 (Direct) |
| FI (2) | FI90088C (Direct) |
| GR (1) | GR3007586T3 (Direct) |
| HU (2) | HU201973B (Direct) |
| IE (2) | IE61483B1 (Direct) |
| IL (2) | IL85118A (Direct) |
| IN (1) | IN167980B (Direct) |
| MA (1) | MA21160A1 (Direct) |
| MY (1) | MY103514A (Direct) |
| NZ (2) | NZ223271A (Direct) |
| PL (2) | PL156763B1 (Direct) |
| PT (2) | PT86583B (Direct) |
| RU (1) | RU1806198C (Direct) |
| SK (1) | SK279351B6 (Direct) |
| YU (1) | YU47878B (Direct) |
| ZA (3) | ZA88448B (Direct) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4806527A (en) * | 1987-03-16 | 1989-02-21 | Merck & Co., Inc. | Avermectin derivatives |
| US4874749A (en) * | 1987-07-31 | 1989-10-17 | Merck & Co., Inc. | 4"-Deoxy-4-N-methylamino avermectin Bla/Blb |
| ES2054822T3 (es) * | 1987-10-23 | 1994-08-16 | Pfizer | Procedimiento para la produccion de agliconas de avermectinas y sus cultivos. |
| GB8807280D0 (en) * | 1988-03-26 | 1988-04-27 | Pfizer Ltd | Antiparasitic agents |
| GB8811036D0 (en) * | 1988-05-10 | 1988-06-15 | Glaxo Group Ltd | Chemical compounds |
| GB8813760D0 (en) * | 1988-06-10 | 1988-07-13 | American Cyanamid Co | Chemical process |
| GB8815967D0 (en) * | 1988-07-05 | 1988-08-10 | Pfizer Ltd | Antiparasitic agents |
| NZ231772A (en) * | 1988-12-23 | 1992-11-25 | Merck & Co Inc | Avermectin derivatives, preparation and parasiticidal compositions thereof |
| NZ231773A (en) * | 1988-12-23 | 1992-09-25 | Merck & Co Inc | Avermectin derivatives, preparation and parasiticidal pharmaceutical compositions thereof |
| US5015630A (en) * | 1989-01-19 | 1991-05-14 | Merck & Co., Inc. | 5-oxime avermectin derivatives |
| US4897383A (en) * | 1989-02-13 | 1990-01-30 | Merck & Co., Inc. | Avermectin derivatives |
| US5252474A (en) * | 1989-03-31 | 1993-10-12 | Merck & Co., Inc. | Cloning genes from Streptomyces avermitilis for avermectin biosynthesis and the methods for their use |
| US5030622A (en) * | 1989-06-02 | 1991-07-09 | Merck & Co., Inc. | Avermectin derivatives |
| US5057499A (en) * | 1989-06-02 | 1991-10-15 | Merck & Co. Inc. | Avermectin derivatives |
| US5023241A (en) * | 1989-07-31 | 1991-06-11 | Merck & Co., Inc. | Avermectin derivatives |
| US5830875A (en) * | 1989-10-30 | 1998-11-03 | Merck & Co., Inc. | 24-and 25-substituted avermectin and milbemycin derivatives |
| JP2888586B2 (ja) * | 1990-03-05 | 1999-05-10 | 社団法人北里研究所 | エバーメクチンの特定成分を選択生産するための微生物およびその選択的製造法 |
| US5169839A (en) * | 1990-05-11 | 1992-12-08 | Merck & Co., Inc. | Derivatives of 3'- and 3"-o-desmethyl avermectin compounds, compositions and methods of treating melmintic and parasitic infections |
| US5208222A (en) * | 1991-03-28 | 1993-05-04 | Merck & Co., Inc. | 4"-and 4'-alkylthio avermectin derivatives |
| US5240915A (en) * | 1991-10-15 | 1993-08-31 | Merck & Co., Inc. | Avermectin derivatives |
| US6103504A (en) * | 1992-03-25 | 2000-08-15 | Pfizer Inc. | Process for production of avermectins and cultures therefor |
| US5292647A (en) * | 1992-11-30 | 1994-03-08 | Eli Lilly And Company | Strain of streptomyces for producing avermectins and processes therewith |
| CN1038330C (zh) * | 1993-07-05 | 1998-05-13 | 塞泰克斯公司 | 阿弗麦菌素的生产与分离 |
| ATE248916T1 (de) * | 1993-07-30 | 2003-09-15 | Pfizer | Gene, die verzweigte-alpha-ketosäure- dehydrogenasekomplexe von streptomyces avermitius kodieren |
| WO1995009863A1 (en) * | 1993-10-05 | 1995-04-13 | Pfizer Inc. | Process and antiparasitic intermediates for doramectin |
| FI942725L (fi) * | 1993-12-16 | 1995-06-17 | Pfizer | Haaraketjuista alfaketohappodenydrogenaasikompleksia koodaavia geenejä Streptomyces avermitiliksesta |
| US5701591A (en) * | 1995-04-07 | 1997-12-23 | Telecommunications Equipment Corporation | Multi-function interactive communications system with circularly/elliptically polarized signal transmission and reception |
| PL194270B1 (pl) * | 1998-02-13 | 2007-05-31 | Pfizer Prod Inc | Wyizolowana cząsteczka polinukleotydowa, cząsteczka oligonukleotydowa, zrekombinowany wektor, komórka gospodarza, wyizolowany produkt genu AveC S. avermitilis, wyizolowany produkt homologu genu AveC S. hygroscopicus, sposób wytwarzania zrekombinowanego produktu genu AveC, sposób wytwarzania zrekombinowanego produktu homologu genu AveC, cząsteczka polinukleotydowa, wektor do zastępowania genu, sposób identyfikowania mutacji otwartej ramki odczytuAveC, sposób wytwarzania nowych szczepów S. avermitilis, szczep S. avermitilis i sposób wytwarzaniaawermektyn |
| IL147563A0 (en) * | 1999-08-12 | 2002-08-14 | Pfizer Prod Inc | Streptomyces avermitilis gene directing the ratio of b2:b1 avermectins |
| KR100415395B1 (ko) * | 2000-08-02 | 2004-01-16 | 한국생명공학연구원 | 에버멕틴 ｂｃ-5-ｏ-메칠트랜스퍼라제의 유전자가 파괴된 스트렙토마이세스 에버미티리스 변이균주 및 그의 제조 방법 |
| KR100718378B1 (ko) | 2002-02-12 | 2007-05-14 | 화이자 프로덕츠 인코포레이티드 | Ｂ2:ｂ1 아베르멕틴의 비를 제어하는 스트렙토마이세스아베르미틸리스 유전자 |
| WO2023203038A1 (en) | 2022-04-19 | 2023-10-26 | Syngenta Crop Protection Ag | Insect, acarina and nematode pest control |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE434277B (sv) | 1976-04-19 | 1984-07-16 | Merck & Co Inc | Sett att framstella nya antihelmintiskt verkande foreningar genom odling av streptomyces avermitilis |
| NZ188459A (en) * | 1977-10-03 | 1982-09-07 | Merck & Co Inc | Derivatives of c-076 compounds and pesticidal compositions |
| US4429042A (en) | 1978-09-08 | 1984-01-31 | Merck & Co., Inc. | Strain of Streptomyces for producing antiparasitic compounds |
| ES8800986A1 (es) * | 1985-07-27 | 1987-12-01 | Pfizer | Un procedimiento para la produccion de un nuevo derivado de avermectina |
| GB8606120D0 (en) * | 1986-03-12 | 1986-04-16 | Glaxo Group Ltd | Process |
-
1987
- 1987-12-10 IN IN1059/DEL/87A patent/IN167980B/en unknown
-
1988
- 1988-01-18 AT AT88300354T patent/ATE96174T1/de not_active IP Right Cessation
- 1988-01-18 EP EP88300354A patent/EP0276103B1/en not_active Expired - Lifetime
- 1988-01-18 IL IL85118A patent/IL85118A/xx not_active IP Right Cessation
- 1988-01-18 DE DE88300354T patent/DE3884973T2/de not_active Expired - Lifetime
- 1988-01-18 ES ES88300354T patent/ES2059498T3/es not_active Expired - Lifetime
- 1988-01-18 BG BG082657A patent/BG51051A3/bg unknown
- 1988-01-19 MA MA21397A patent/MA21160A1/fr unknown
- 1988-01-19 MY MYPI88000037A patent/MY103514A/en unknown
- 1988-01-20 EP EP88300426A patent/EP0276131B1/en not_active Expired - Lifetime
- 1988-01-20 AT AT88300426T patent/ATE87927T1/de not_active IP Right Cessation
- 1988-01-20 ES ES88300426T patent/ES2053719T3/es not_active Expired - Lifetime
- 1988-01-20 DE DE8888300426T patent/DE3879975T2/de not_active Expired - Lifetime
- 1988-01-21 PL PL1988270238A patent/PL156763B1/pl unknown
- 1988-01-21 PL PL1988270239A patent/PL156764B1/pl unknown
- 1988-01-21 IL IL85165A patent/IL85165A/xx not_active IP Right Cessation
- 1988-01-21 SK SK407-88A patent/SK279351B6/sk unknown
- 1988-01-21 CZ CS88407A patent/CZ279782B6/cs unknown
- 1988-01-21 EG EG3588A patent/EG18797A/xx active
- 1988-01-21 PT PT86583A patent/PT86583B/pt unknown
- 1988-01-21 PT PT86584A patent/PT86584B/pt unknown
- 1988-01-22 DK DK028988A patent/DK28988A/da not_active Application Discontinuation
- 1988-01-22 AU AU10696/88A patent/AU595673B2/en not_active Expired
- 1988-01-22 DD DD88312394A patent/DD267512A5/de unknown
- 1988-01-22 NZ NZ223271A patent/NZ223271A/en unknown
- 1988-01-22 KR KR1019880000470A patent/KR900004419B1/ko not_active Expired
- 1988-01-22 ZA ZA88448A patent/ZA88448B/xx unknown
- 1988-01-22 DD DD88312393A patent/DD290214A5/de unknown
- 1988-01-22 IE IE16088A patent/IE61483B1/en not_active IP Right Cessation
- 1988-01-22 CN CN88100649A patent/CN1056883C/zh not_active Expired - Lifetime
- 1988-01-22 YU YU11988A patent/YU47878B/sh unknown
- 1988-01-22 RU SU884355079A patent/RU1806198C/ru active
- 1988-01-22 HU HU88260D patent/HU201973B/hu unknown
- 1988-01-22 FI FI880281A patent/FI90088C/fi not_active IP Right Cessation
- 1988-01-22 ZA ZA88447A patent/ZA88447B/xx unknown
- 1988-01-22 FI FI880280A patent/FI90091C/fi not_active IP Right Cessation
- 1988-01-22 NZ NZ223272A patent/NZ223272A/xx unknown
- 1988-01-22 DK DK198800290A patent/DK175720B1/da not_active IP Right Cessation
- 1988-01-22 AR AR88309888A patent/AR241798A1/es active
- 1988-01-22 IE IE16188A patent/IE61066B1/en not_active IP Right Cessation
- 1988-01-22 JP JP63012462A patent/JPH0681757B2/ja not_active Expired - Lifetime
- 1988-01-22 HU HU88261A patent/HU200487B/hu unknown
- 1988-01-22 ZA ZA88449A patent/ZA88449B/xx unknown
- 1988-01-23 KR KR1019880000506A patent/KR910002225B1/ko not_active Expired
- 1988-01-23 JP JP63011881A patent/JPH0817693B2/ja not_active Expired - Lifetime
- 1988-01-25 BR BRPI8800271-3A patent/BR8800271A/pt not_active IP Right Cessation
-
1991
- 1991-02-15 AU AU71110/91A patent/AU631298B2/en not_active Expired
-
1993
- 1993-04-08 GR GR930400638T patent/GR3007586T3/el unknown
Non-Patent Citations (1)
| Title |
|---|
| ПатентСША№4310519, кл.А61 К31/71, 1982. Патент GB № 4429042, кл. А 61 К 31/71, 1983. Патент СССР N 1560059, кл. С 12 Р 17/08, 1986. * |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU1806198C (ru) | Способ получени авермектина В | |
| HU182069B (en) | Process for preparing monacoline k, a compound with antihypercholesteremic activity | |
| EP3112470A1 (en) | Method for producing antimicrobial agents | |
| JPS58165786A (ja) | クロストリジウム・アセトブチリカムのブタノールおよびアセトン高生産性突然変異体の創製方法 | |
| US7279314B2 (en) | Chemical substance having morphogenetic and growth-accelerating activities | |
| US7202063B1 (en) | Processes for the production of rhamnolipids | |
| Boeck et al. | NEW AZASTEROIDAL ANTIFUNGAL ANTIBIOTICS FROM GEOTRICHU FLAVO-BRUNNEUM I. DISCOVERY AND FERMENTATION STUDIES | |
| KR960016874B1 (ko) | 미생물에 의한 트랜스-4-히드록시-l-프롤린의 제조방법 | |
| PL122463B1 (en) | Process for preparing novel c-15003 p-3 antibiotic | |
| RU2080382C1 (ru) | Штамм бактерий clostridium acetobutylicum-продуцент н-бутилового спирта и ацетона | |
| CA2015940A1 (en) | Antifungal agent | |
| EP0478061A1 (en) | Antiviral agent | |
| JPH01193265A (ja) | 新規抗腫瘍性抗生物質ｓｆ２５８７物質及びその製造法 | |
| Venkata Dasu et al. | Studies on production of griseofulvin | |
| US4298600A (en) | Antibiotic C-14482 A1 and method for producing same | |
| US3884762A (en) | Fermentation process for the preparation of ergot alkaloids | |
| CN108486180A (zh) | 一种卵孢菌素的发酵制备方法 | |
| US5276055A (en) | Antibiotic agents | |
| HU189515B (en) | Process for preparing new 20-dihydro-20,23-dideoxy-tylonolide /tylactone/ and esters thereof | |
| Yoshikawa et al. | Terminal steps in the biosynthesis of herbicidins, nucleoside antibiotics | |
| Boeck et al. | A32390A, A NEW BIOLOGICALLY ACTIVE METABOLITE I. DISCOVERY AND FERMENTATION STUDIES | |
| EP0522715A1 (en) | Squalene synthethase inhibitors and processes therefrom | |
| US3954970A (en) | Actinomycin complex from micromonospora | |
| KR850001939B1 (ko) | A-32724 항생물질의 제조방법 | |
| US5304485A (en) | Antibiotic producing microorganism |