BE553388A - - Google Patents
Info
- Publication number
- BE553388A BE553388A BE553388DA BE553388A BE 553388 A BE553388 A BE 553388A BE 553388D A BE553388D A BE 553388DA BE 553388 A BE553388 A BE 553388A
- Authority
- BE
- Belgium
- Prior art keywords
- sep
- dihydrostreptomycin
- sulfate
- antibiotic
- desc
- Prior art date
Links
- ASXBYYWOLISCLQ-HZYVHMACSA-N dihydrostreptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](CO)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O ASXBYYWOLISCLQ-HZYVHMACSA-N 0.000 claims description 64
- ASXBYYWOLISCLQ-UHFFFAOYSA-N Dihydrostreptomycin Natural products O1C(CO)C(O)C(O)C(NC)C1OC1C(CO)(O)C(C)OC1OC1C(N=C(N)N)C(O)C(N=C(N)N)C(O)C1O ASXBYYWOLISCLQ-UHFFFAOYSA-N 0.000 claims description 61
- 229960002222 dihydrostreptomycin Drugs 0.000 claims description 61
- 230000003115 biocidal effect Effects 0.000 claims description 48
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 claims description 34
- 229960005322 streptomycin Drugs 0.000 claims description 17
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 13
- 238000001228 spectrum Methods 0.000 claims description 9
- 230000008859 change Effects 0.000 claims description 7
- 238000012360 testing method Methods 0.000 claims description 5
- 238000000855 fermentation Methods 0.000 claims description 4
- 230000004151 fermentation Effects 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 45
- 241001465754 Metazoa Species 0.000 claims 33
- 239000000243 solution Substances 0.000 claims 33
- 238000000034 method Methods 0.000 claims 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 27
- 229910001868 water Inorganic materials 0.000 claims 27
- 150000001875 compounds Chemical class 0.000 claims 26
- 239000012535 impurity Substances 0.000 claims 24
- 239000000126 substance Substances 0.000 claims 24
- 210000004185 liver Anatomy 0.000 claims 22
- 235000010633 broth Nutrition 0.000 claims 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 19
- 210000004072 lung Anatomy 0.000 claims 19
- 239000002609 medium Substances 0.000 claims 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 16
- 150000003839 salts Chemical class 0.000 claims 16
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 14
- 241000187747 Streptomyces Species 0.000 claims 14
- 230000008569 process Effects 0.000 claims 14
- 239000002904 solvent Substances 0.000 claims 14
- CZWJCQXZZJHHRH-YCRXJPFRSA-N 2-[(1r,2r,3s,4r,5r,6s)-3-(diaminomethylideneamino)-4-[(2r,3r,4r,5s)-3-[(2s,3s,4s,5r,6s)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)oxan-2-yl]oxy-4-hydroxy-4-(hydroxymethyl)-5-methyloxolan-2-yl]oxy-2,5,6-trihydroxycyclohexyl]guanidine;sulfuric acid Chemical compound OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](CO)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](N=C(N)N)[C@H](O)[C@@H](N=C(N)N)[C@H](O)[C@H]1O.CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](CO)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](N=C(N)N)[C@H](O)[C@@H](N=C(N)N)[C@H](O)[C@H]1O CZWJCQXZZJHHRH-YCRXJPFRSA-N 0.000 claims 13
- 229920001817 Agar Polymers 0.000 claims 13
- 239000008272 agar Substances 0.000 claims 13
- 244000005700 microbiome Species 0.000 claims 13
- 239000000203 mixture Substances 0.000 claims 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 12
- 229960001162 dihydrostreptomycin sulfate Drugs 0.000 claims 12
- 201000008827 tuberculosis Diseases 0.000 claims 12
- 241000193830 Bacillus <bacterium> Species 0.000 claims 11
- 238000010790 dilution Methods 0.000 claims 11
- 239000012895 dilution Substances 0.000 claims 11
- 230000000694 effects Effects 0.000 claims 11
- 210000002751 lymph Anatomy 0.000 claims 11
- 239000000463 material Substances 0.000 claims 11
- 239000000284 extract Substances 0.000 claims 10
- 208000015181 infectious disease Diseases 0.000 claims 10
- 239000002244 precipitate Substances 0.000 claims 10
- 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 claims 9
- 235000010469 Glycine max Nutrition 0.000 claims 9
- 108010080698 Peptones Proteins 0.000 claims 9
- 229920002472 Starch Polymers 0.000 claims 9
- 240000008042 Zea mays Species 0.000 claims 9
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims 9
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims 9
- 239000003242 anti bacterial agent Substances 0.000 claims 9
- 229940088710 antibiotic agent Drugs 0.000 claims 9
- 238000006243 chemical reaction Methods 0.000 claims 9
- 239000003795 chemical substances by application Substances 0.000 claims 9
- 235000005822 corn Nutrition 0.000 claims 9
- 235000013312 flour Nutrition 0.000 claims 9
- 239000008103 glucose Substances 0.000 claims 9
- 239000000047 product Substances 0.000 claims 9
- 241000894007 species Species 0.000 claims 9
- 235000019698 starch Nutrition 0.000 claims 9
- 239000008107 starch Substances 0.000 claims 9
- 239000001888 Peptone Substances 0.000 claims 8
- 239000000706 filtrate Substances 0.000 claims 8
- 235000019319 peptone Nutrition 0.000 claims 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 7
- 239000002253 acid Substances 0.000 claims 7
- 239000003463 adsorbent Substances 0.000 claims 7
- 229910052799 carbon Inorganic materials 0.000 claims 7
- 239000006071 cream Substances 0.000 claims 7
- 239000013078 crystal Substances 0.000 claims 7
- 238000011161 development Methods 0.000 claims 7
- 229910052757 nitrogen Inorganic materials 0.000 claims 7
- 235000018102 proteins Nutrition 0.000 claims 7
- 108090000623 proteins and genes Proteins 0.000 claims 7
- 102000004169 proteins and genes Human genes 0.000 claims 7
- 238000000926 separation method Methods 0.000 claims 7
- 239000011780 sodium chloride Substances 0.000 claims 7
- 239000007787 solid Substances 0.000 claims 7
- 229910021653 sulphate ion Inorganic materials 0.000 claims 7
- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 claims 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 6
- 235000014469 Bacillus subtilis Nutrition 0.000 claims 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 6
- 244000068988 Glycine max Species 0.000 claims 6
- 241000699670 Mus sp. Species 0.000 claims 6
- 230000000844 anti-bacterial effect Effects 0.000 claims 6
- 239000002585 base Substances 0.000 claims 6
- 238000010828 elution Methods 0.000 claims 6
- 238000000605 extraction Methods 0.000 claims 6
- 239000001963 growth medium Substances 0.000 claims 6
- 235000013372 meat Nutrition 0.000 claims 6
- 239000003960 organic solvent Substances 0.000 claims 6
- 238000002791 soaking Methods 0.000 claims 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 5
- MSXMXWJPFIDEMT-UHFFFAOYSA-N Streptidine Natural products NC(N)=NC1C(O)C(O)C(O)C(N=C(N)N)C1O MSXMXWJPFIDEMT-UHFFFAOYSA-N 0.000 claims 5
- 241000509472 Streptomyces humidus Species 0.000 claims 5
- 230000002378 acidificating effect Effects 0.000 claims 5
- 238000011888 autopsy Methods 0.000 claims 5
- 239000005018 casein Substances 0.000 claims 5
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 claims 5
- 235000021240 caseins Nutrition 0.000 claims 5
- 238000012258 culturing Methods 0.000 claims 5
- 235000013601 eggs Nutrition 0.000 claims 5
- 150000002500 ions Chemical class 0.000 claims 5
- 239000007788 liquid Substances 0.000 claims 5
- 229940075930 picrate Drugs 0.000 claims 5
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 claims 5
- 230000001376 precipitating effect Effects 0.000 claims 5
- 238000011084 recovery Methods 0.000 claims 5
- 229920005989 resin Polymers 0.000 claims 5
- 239000011347 resin Substances 0.000 claims 5
- MSXMXWJPFIDEMT-FAEUDGQSSA-N streptidine Chemical compound NC(=N)N[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](NC(N)=N)[C@@H]1O MSXMXWJPFIDEMT-FAEUDGQSSA-N 0.000 claims 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 4
- 240000006890 Erythroxylum coca Species 0.000 claims 4
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- 241001481789 Rupicapra Species 0.000 claims 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 4
- 239000007864 aqueous solution Substances 0.000 claims 4
- 239000003125 aqueous solvent Substances 0.000 claims 4
- 230000000973 chemotherapeutic effect Effects 0.000 claims 4
- 235000008957 cocaer Nutrition 0.000 claims 4
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims 4
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims 4
- 235000018417 cysteine Nutrition 0.000 claims 4
- 235000014113 dietary fatty acids Nutrition 0.000 claims 4
- 229940079593 drug Drugs 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 239000000194 fatty acid Substances 0.000 claims 4
- 229930195729 fatty acid Natural products 0.000 claims 4
- 150000004665 fatty acids Chemical class 0.000 claims 4
- 235000020094 liqueur Nutrition 0.000 claims 4
- 238000002844 melting Methods 0.000 claims 4
- 230000008018 melting Effects 0.000 claims 4
- 230000002441 reversible effect Effects 0.000 claims 4
- 239000000779 smoke Substances 0.000 claims 4
- 239000011734 sodium Substances 0.000 claims 4
- 235000011121 sodium hydroxide Nutrition 0.000 claims 4
- 210000000952 spleen Anatomy 0.000 claims 4
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 claims 3
- WEEMDRWIKYCTQM-UHFFFAOYSA-N 2,6-dimethoxybenzenecarbothioamide Chemical compound COC1=CC=CC(OC)=C1C(N)=S WEEMDRWIKYCTQM-UHFFFAOYSA-N 0.000 claims 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical class [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 3
- 229920001353 Dextrin Polymers 0.000 claims 3
- 239000004375 Dextrin Substances 0.000 claims 3
- 241000588724 Escherichia coli Species 0.000 claims 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 claims 3
- HYMLWHLQFGRFIY-UHFFFAOYSA-N Maltol Natural products CC1OC=CC(=O)C1=O HYMLWHLQFGRFIY-UHFFFAOYSA-N 0.000 claims 3
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 claims 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims 3
- 235000019764 Soybean Meal Nutrition 0.000 claims 3
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims 3
- 229930006000 Sucrose Natural products 0.000 claims 3
- 238000000862 absorption spectrum Methods 0.000 claims 3
- 239000011575 calcium Substances 0.000 claims 3
- 229910052791 calcium Inorganic materials 0.000 claims 3
- 150000001720 carbohydrates Chemical class 0.000 claims 3
- 235000014633 carbohydrates Nutrition 0.000 claims 3
- 238000004587 chromatography analysis Methods 0.000 claims 3
- 235000019425 dextrin Nutrition 0.000 claims 3
- 238000009826 distribution Methods 0.000 claims 3
- 238000001914 filtration Methods 0.000 claims 3
- 210000004907 gland Anatomy 0.000 claims 3
- 235000011187 glycerol Nutrition 0.000 claims 3
- 238000010438 heat treatment Methods 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 230000005764 inhibitory process Effects 0.000 claims 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 3
- 239000008101 lactose Substances 0.000 claims 3
- 229940043353 maltol Drugs 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- STZCRXQWRGQSJD-GEEYTBSJSA-M methyl orange Chemical compound [Na+].C1=CC(N(C)C)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 STZCRXQWRGQSJD-GEEYTBSJSA-M 0.000 claims 3
- 229940012189 methyl orange Drugs 0.000 claims 3
- 235000010755 mineral Nutrition 0.000 claims 3
- 239000011707 mineral Substances 0.000 claims 3
- 230000035772 mutation Effects 0.000 claims 3
- 239000002504 physiological saline solution Substances 0.000 claims 3
- 239000000843 powder Substances 0.000 claims 3
- 238000001556 precipitation Methods 0.000 claims 3
- 230000009467 reduction Effects 0.000 claims 3
- 238000001179 sorption measurement Methods 0.000 claims 3
- 239000004455 soybean meal Substances 0.000 claims 3
- 238000003756 stirring Methods 0.000 claims 3
- 229960002385 streptomycin sulfate Drugs 0.000 claims 3
- 239000005720 sucrose Substances 0.000 claims 3
- OFNXOACBUMGOPC-HZYVHMACSA-N 5'-hydroxystreptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](CO)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O OFNXOACBUMGOPC-HZYVHMACSA-N 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 2
- 241000700198 Cavia Species 0.000 claims 2
- 241000700199 Cavia porcellus Species 0.000 claims 2
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 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 claims 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical class [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical class [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims 2
- 229910002651 NO3 Inorganic materials 0.000 claims 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 244000269722 Thea sinensis Species 0.000 claims 2
- 230000009471 action Effects 0.000 claims 2
- 235000001014 amino acid Nutrition 0.000 claims 2
- 229940024606 amino acid Drugs 0.000 claims 2
- 150000001413 amino acids Chemical class 0.000 claims 2
- 238000004458 analytical method Methods 0.000 claims 2
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 claims 2
- 239000004202 carbamide Substances 0.000 claims 2
- 150000001768 cations Chemical class 0.000 claims 2
- 238000001816 cooling Methods 0.000 claims 2
- 238000003113 dilution method Methods 0.000 claims 2
- 238000004821 distillation Methods 0.000 claims 2
- 238000002474 experimental method Methods 0.000 claims 2
- OFNXOACBUMGOPC-UHFFFAOYSA-N hydroxystreptomycin Natural products CNC1C(O)C(O)C(CO)OC1OC1C(C=O)(O)C(CO)OC1OC1C(N=C(N)N)C(O)C(N=C(N)N)C(O)C1O OFNXOACBUMGOPC-UHFFFAOYSA-N 0.000 claims 2
- 238000000338 in vitro Methods 0.000 claims 2
- 238000002347 injection Methods 0.000 claims 2
- 239000007924 injection Substances 0.000 claims 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 claims 2
- 238000002955 isolation Methods 0.000 claims 2
- 230000003902 lesion Effects 0.000 claims 2
- 238000009630 liquid culture Methods 0.000 claims 2
- 230000001926 lymphatic effect Effects 0.000 claims 2
- 239000011777 magnesium Chemical class 0.000 claims 2
- 229910052749 magnesium Inorganic materials 0.000 claims 2
- 230000004060 metabolic process Effects 0.000 claims 2
- 239000002207 metabolite Substances 0.000 claims 2
- 231100000350 mutagenesis Toxicity 0.000 claims 2
- 235000015097 nutrients Nutrition 0.000 claims 2
- 230000000050 nutritive effect Effects 0.000 claims 2
- 230000009965 odorless effect Effects 0.000 claims 2
- 210000000056 organ Anatomy 0.000 claims 2
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- 238000000746 purification Methods 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- 239000011541 reaction mixture Substances 0.000 claims 2
- 239000012047 saturated solution Substances 0.000 claims 2
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 claims 2
- 229910052708 sodium Inorganic materials 0.000 claims 2
- 235000000346 sugar Nutrition 0.000 claims 2
- 150000008163 sugars Chemical class 0.000 claims 2
- 230000001225 therapeutic effect Effects 0.000 claims 2
- 231100000419 toxicity Toxicity 0.000 claims 2
- 230000001988 toxicity Effects 0.000 claims 2
- 229960001005 tuberculin Drugs 0.000 claims 2
- 235000013311 vegetables Nutrition 0.000 claims 2
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- 229950005779 carbomycin Drugs 0.000 claims 1
- XEVRDFDBXJMZFG-UHFFFAOYSA-N carbonyl dihydrazine Chemical compound NNC(=O)NN XEVRDFDBXJMZFG-UHFFFAOYSA-N 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
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- FBPFZTCFMRRESA-GUCUJZIJSA-N galactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-GUCUJZIJSA-N 0.000 claims 1
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- FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 claims 1
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- JYJIGFIDKWBXDU-MNNPPOADSA-N inulin Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)OC[C@]1(OC[C@]2(OC[C@]3(OC[C@]4(OC[C@]5(OC[C@]6(OC[C@]7(OC[C@]8(OC[C@]9(OC[C@]%10(OC[C@]%11(OC[C@]%12(OC[C@]%13(OC[C@]%14(OC[C@]%15(OC[C@]%16(OC[C@]%17(OC[C@]%18(OC[C@]%19(OC[C@]%20(OC[C@]%21(OC[C@]%22(OC[C@]%23(OC[C@]%24(OC[C@]%25(OC[C@]%26(OC[C@]%27(OC[C@]%28(OC[C@]%29(OC[C@]%30(OC[C@]%31(OC[C@]%32(OC[C@]%33(OC[C@]%34(OC[C@]%35(OC[C@]%36(O[C@@H]%37[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O%37)O)[C@H]([C@H](O)[C@@H](CO)O%36)O)[C@H]([C@H](O)[C@@H](CO)O%35)O)[C@H]([C@H](O)[C@@H](CO)O%34)O)[C@H]([C@H](O)[C@@H](CO)O%33)O)[C@H]([C@H](O)[C@@H](CO)O%32)O)[C@H]([C@H](O)[C@@H](CO)O%31)O)[C@H]([C@H](O)[C@@H](CO)O%30)O)[C@H]([C@H](O)[C@@H](CO)O%29)O)[C@H]([C@H](O)[C@@H](CO)O%28)O)[C@H]([C@H](O)[C@@H](CO)O%27)O)[C@H]([C@H](O)[C@@H](CO)O%26)O)[C@H]([C@H](O)[C@@H](CO)O%25)O)[C@H]([C@H](O)[C@@H](CO)O%24)O)[C@H]([C@H](O)[C@@H](CO)O%23)O)[C@H]([C@H](O)[C@@H](CO)O%22)O)[C@H]([C@H](O)[C@@H](CO)O%21)O)[C@H]([C@H](O)[C@@H](CO)O%20)O)[C@H]([C@H](O)[C@@H](CO)O%19)O)[C@H]([C@H](O)[C@@H](CO)O%18)O)[C@H]([C@H](O)[C@@H](CO)O%17)O)[C@H]([C@H](O)[C@@H](CO)O%16)O)[C@H]([C@H](O)[C@@H](CO)O%15)O)[C@H]([C@H](O)[C@@H](CO)O%14)O)[C@H]([C@H](O)[C@@H](CO)O%13)O)[C@H]([C@H](O)[C@@H](CO)O%12)O)[C@H]([C@H](O)[C@@H](CO)O%11)O)[C@H]([C@H](O)[C@@H](CO)O%10)O)[C@H]([C@H](O)[C@@H](CO)O9)O)[C@H]([C@H](O)[C@@H](CO)O8)O)[C@H]([C@H](O)[C@@H](CO)O7)O)[C@H]([C@H](O)[C@@H](CO)O6)O)[C@H]([C@H](O)[C@@H](CO)O5)O)[C@H]([C@H](O)[C@@H](CO)O4)O)[C@H]([C@H](O)[C@@H](CO)O3)O)[C@H]([C@H](O)[C@@H](CO)O2)O)[C@@H](O)[C@H](O)[C@@H](CO)O1 JYJIGFIDKWBXDU-MNNPPOADSA-N 0.000 claims 1
- 229940029339 inulin Drugs 0.000 claims 1
- 239000003456 ion exchange resin Substances 0.000 claims 1
- 229920003303 ion-exchange polymer Polymers 0.000 claims 1
- 229910052742 iron Inorganic materials 0.000 claims 1
- BJHIKXHVCXFQLS-UYFOZJQFSA-N keto-D-fructose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C(=O)CO BJHIKXHVCXFQLS-UYFOZJQFSA-N 0.000 claims 1
- 231100000636 lethal dose Toxicity 0.000 claims 1
- 150000002632 lipids Chemical class 0.000 claims 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims 1
- 235000019341 magnesium sulphate Nutrition 0.000 claims 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical class [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
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- 230000003287 optical effect Effects 0.000 claims 1
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- 235000006408 oxalic acid Nutrition 0.000 claims 1
- 238000010979 pH adjustment Methods 0.000 claims 1
- 150000002989 phenols Chemical class 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- IYDGMDWEHDFVQI-UHFFFAOYSA-N phosphoric acid;trioxotungsten Chemical compound O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O IYDGMDWEHDFVQI-UHFFFAOYSA-N 0.000 claims 1
- 239000000049 pigment Substances 0.000 claims 1
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- 238000010791 quenching Methods 0.000 claims 1
- 230000000171 quenching effect Effects 0.000 claims 1
- MUPFEKGTMRGPLJ-ZQSKZDJDSA-N raffinose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)O1 MUPFEKGTMRGPLJ-ZQSKZDJDSA-N 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 claims 1
- 235000009566 rice Nutrition 0.000 claims 1
- NGFMICBWJRZIBI-UJPOAAIJSA-N salicin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=CC=C1CO NGFMICBWJRZIBI-UJPOAAIJSA-N 0.000 claims 1
- 229940120668 salicin Drugs 0.000 claims 1
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- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 235000015067 sauces Nutrition 0.000 claims 1
- 239000000741 silica gel Substances 0.000 claims 1
- 229910002027 silica gel Inorganic materials 0.000 claims 1
- 229910052709 silver Inorganic materials 0.000 claims 1
- 239000004332 silver Substances 0.000 claims 1
- 239000002002 slurry Substances 0.000 claims 1
- STZCRXQWRGQSJD-UHFFFAOYSA-M sodium;4-[[4-(dimethylamino)phenyl]diazenyl]benzenesulfonate Chemical compound [Na+].C1=CC(N(C)C)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 STZCRXQWRGQSJD-UHFFFAOYSA-M 0.000 claims 1
- 239000002689 soil Substances 0.000 claims 1
- 239000011343 solid material Substances 0.000 claims 1
- 239000012265 solid product Substances 0.000 claims 1
- 238000010561 standard procedure Methods 0.000 claims 1
- 239000010902 straw Substances 0.000 claims 1
- QTENRWWVYAAPBI-YCRXJPFRSA-N streptomycin sulfate Chemical compound OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](N=C(N)N)[C@H](O)[C@@H](N=C(N)N)[C@H](O)[C@H]1O.CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](N=C(N)N)[C@H](O)[C@@H](N=C(N)N)[C@H](O)[C@H]1O QTENRWWVYAAPBI-YCRXJPFRSA-N 0.000 claims 1
- 238000010254 subcutaneous injection Methods 0.000 claims 1
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- 238000002560 therapeutic procedure Methods 0.000 claims 1
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- 238000002211 ultraviolet spectrum Methods 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- 239000011701 zinc Substances 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
Classifications
-
- 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
- C12P19/46—Preparation of O-glycosides, e.g. glucosides having an oxygen atom of the saccharide radical bound to a cyclohexyl radical, e.g. kasugamycin
- C12P19/54—Preparation of O-glycosides, e.g. glucosides having an oxygen atom of the saccharide radical bound to a cyclohexyl radical, e.g. kasugamycin the cyclohexyl radical being bound directly to a nitrogen atom of two or more radicals, e.g. streptomycin
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE553388A true BE553388A (en:Method) |
Family
ID=178219
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE553388D BE553388A (en:Method) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE553388A (en:Method) |
-
0
- BE BE553388D patent/BE553388A/fr unknown
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