BE536231A - - Google Patents

Info

Publication number

BE536231A

BE536231A BE536231DA BE536231A BE 536231 A BE536231 A BE 536231A BE 536231D A BE536231D A BE 536231DA BE 536231 A BE536231 A BE 536231A

Authority

BE

Belgium

Prior art keywords

tetracycline

chlortetracycline

water

solution

sep

Prior art date

Links

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• Global Dossier
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• 229930101283 tetracycline Natural products 0.000 claims description 41
• 239000004098 Tetracycline Substances 0.000 claims description 40
• 229960002180 tetracycline Drugs 0.000 claims description 40
• 235000019364 tetracycline Nutrition 0.000 claims description 40
• 150000003522 tetracyclines Chemical class 0.000 claims description 40
• CYDMQBQPVICBEU-XRNKAMNCSA-N chlortetracycline Chemical compound C1=CC(Cl)=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O CYDMQBQPVICBEU-XRNKAMNCSA-N 0.000 claims description 30
• 229960004475 chlortetracycline Drugs 0.000 claims description 30
• CYDMQBQPVICBEU-UHFFFAOYSA-N chlorotetracycline Natural products C1=CC(Cl)=C2C(O)(C)C3CC4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O CYDMQBQPVICBEU-UHFFFAOYSA-N 0.000 claims description 29
• 235000019365 chlortetracycline Nutrition 0.000 claims description 29
• 239000004099 Chlortetracycline Substances 0.000 claims description 28
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
• 239000000203 mixture Substances 0.000 claims description 25
• 239000000243 solution Substances 0.000 claims description 25
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical group CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 24
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
• 239000007864 aqueous solution Substances 0.000 claims description 15
• 238000000034 method Methods 0.000 claims description 15
• 239000003960 organic solvent Substances 0.000 claims description 15
• 239000003242 anti bacterial agent Substances 0.000 claims description 14
• 229940088710 antibiotic agent Drugs 0.000 claims description 14
• 239000000284 extract Substances 0.000 claims description 13
• 150000003839 salts Chemical class 0.000 claims description 10
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
• 239000008346 aqueous phase Substances 0.000 claims description 2
• 239000012141 concentrate Substances 0.000 claims 1
• 238000001816 cooling Methods 0.000 claims 1
• 230000000694 effects Effects 0.000 description 13
• 235000010633 broth Nutrition 0.000 description 12
• 238000000855 fermentation Methods 0.000 description 12
• 230000004151 fermentation Effects 0.000 description 12
• 230000003115 biocidal effect Effects 0.000 description 11
• 235000002639 sodium chloride Nutrition 0.000 description 11
• 238000000605 extraction Methods 0.000 description 8
• 239000000706 filtrate Substances 0.000 description 8
• 239000000047 product Substances 0.000 description 8
• 239000000463 material Substances 0.000 description 5
• 238000000926 separation method Methods 0.000 description 5
• 235000011121 sodium hydroxide Nutrition 0.000 description 5
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
• 238000010531 catalytic reduction reaction Methods 0.000 description 4
• 239000000126 substance Substances 0.000 description 4
• 238000011282 treatment Methods 0.000 description 4
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
• 239000002253 acid Substances 0.000 description 3
• 239000002585 base Substances 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
• 238000001914 filtration Methods 0.000 description 3
• 238000005984 hydrogenation reaction Methods 0.000 description 3
• 235000015097 nutrients Nutrition 0.000 description 3
• 238000001556 precipitation Methods 0.000 description 3
• 239000002904 solvent Substances 0.000 description 3
• 238000005406 washing Methods 0.000 description 3
• NWXMGUDVXFXRIG-WESIUVDSSA-N (4s,4as,5as,6s,12ar)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide Chemical compound C1=CC=C2[C@](O)(C)[C@H]3C[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 NWXMGUDVXFXRIG-WESIUVDSSA-N 0.000 description 2
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
• 235000010469 Glycine max Nutrition 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
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
• WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
• 241000187747 Streptomyces Species 0.000 description 2
• 230000002378 acidificating effect Effects 0.000 description 2
• VBIXEXWLHSRNKB-UHFFFAOYSA-N ammonium oxalate Chemical compound [NH4+].[NH4+].[O-]C(=O)C([O-])=O VBIXEXWLHSRNKB-UHFFFAOYSA-N 0.000 description 2
• 238000004458 analytical method Methods 0.000 description 2
• 239000002021 butanolic extract Substances 0.000 description 2
• 239000013078 crystal Substances 0.000 description 2
• 238000012258 culturing Methods 0.000 description 2
• ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
• 238000004519 manufacturing process Methods 0.000 description 2
• 230000020477 pH reduction Effects 0.000 description 2
• 239000000276 potassium ferrocyanide Substances 0.000 description 2
• 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
• 239000011734 sodium Substances 0.000 description 2
• 229910052708 sodium Inorganic materials 0.000 description 2
• 239000011780 sodium chloride Substances 0.000 description 2
• 239000007787 solid Substances 0.000 description 2
• 238000012360 testing method Methods 0.000 description 2
• XOGGUFAVLNCTRS-UHFFFAOYSA-N tetrapotassium;iron(2+);hexacyanide Chemical compound [K+].[K+].[K+].[K+].[Fe+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] XOGGUFAVLNCTRS-UHFFFAOYSA-N 0.000 description 2
• NWXMGUDVXFXRIG-NAOJVREFSA-N (4s,4as,5as,12ar)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide Chemical compound C1=CC=C2C(O)(C)[C@H]3C[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 NWXMGUDVXFXRIG-NAOJVREFSA-N 0.000 description 1
• ACTFDRRTVUIDFZ-ZZEGOUJXSA-N (4s,4as,5as,6s,12ar)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide;trihydrate Chemical compound O.O.O.C1=CC=C2[C@](O)(C)[C@H]3C[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 ACTFDRRTVUIDFZ-ZZEGOUJXSA-N 0.000 description 1
• 229920001817 Agar Polymers 0.000 description 1
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
• BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
• UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
• 244000068988 Glycine max Species 0.000 description 1
• 241000186984 Kitasatospora aureofaciens Species 0.000 description 1
• AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical class CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
• 229910002651 NO3 Inorganic materials 0.000 description 1
• NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
• 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
• 150000007513 acids Chemical class 0.000 description 1
• 238000005273 aeration Methods 0.000 description 1
• 239000008272 agar Substances 0.000 description 1
• 238000013019 agitation Methods 0.000 description 1
• 150000001298 alcohols Chemical class 0.000 description 1
• -1 aliphatic amines Chemical class 0.000 description 1
• 150000003973 alkyl amines Chemical group 0.000 description 1
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
• 150000001412 amines Chemical class 0.000 description 1
• 235000019270 ammonium chloride Nutrition 0.000 description 1
• 239000000908 ammonium hydroxide Substances 0.000 description 1
• BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
• 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
• 235000011130 ammonium sulphate Nutrition 0.000 description 1
• 239000011575 calcium Substances 0.000 description 1
• 229910052791 calcium Inorganic materials 0.000 description 1
• 229910001424 calcium ion Inorganic materials 0.000 description 1
• 159000000007 calcium salts Chemical class 0.000 description 1
• 239000003054 catalyst Substances 0.000 description 1
• 239000003795 chemical substances by application Substances 0.000 description 1
• 238000004587 chromatography analysis Methods 0.000 description 1
• 238000004040 coloring Methods 0.000 description 1
• 238000002425 crystallisation Methods 0.000 description 1
• 230000008025 crystallization Effects 0.000 description 1
• JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
• 238000001704 evaporation Methods 0.000 description 1
• 230000008020 evaporation Effects 0.000 description 1
• 239000012065 filter cake Substances 0.000 description 1
• 235000013312 flour Nutrition 0.000 description 1
• 239000012458 free base Substances 0.000 description 1
• ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical class CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 1
• 230000000977 initiatory effect Effects 0.000 description 1
• 239000002054 inoculum Substances 0.000 description 1
• 238000005259 measurement Methods 0.000 description 1
• 230000004060 metabolic process Effects 0.000 description 1
• 244000005700 microbiome Species 0.000 description 1
• 150000007522 mineralic acids Chemical class 0.000 description 1
• 238000002156 mixing Methods 0.000 description 1
• 238000012986 modification Methods 0.000 description 1
• 230000004048 modification Effects 0.000 description 1
• 230000007935 neutral effect Effects 0.000 description 1
• 230000003472 neutralizing effect Effects 0.000 description 1
• 239000001103 potassium chloride Substances 0.000 description 1
• 235000011164 potassium chloride Nutrition 0.000 description 1
• OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
• 229910052939 potassium sulfate Inorganic materials 0.000 description 1
• 235000011151 potassium sulphates Nutrition 0.000 description 1
• 239000002244 precipitate Substances 0.000 description 1
• 230000001376 precipitating effect Effects 0.000 description 1
• 238000002360 preparation method Methods 0.000 description 1
• 238000012545 processing Methods 0.000 description 1
• 238000000746 purification Methods 0.000 description 1
• 125000001453 quaternary ammonium group Chemical group 0.000 description 1
• 238000001953 recrystallisation Methods 0.000 description 1
• 238000006722 reduction reaction Methods 0.000 description 1
• 238000005057 refrigeration Methods 0.000 description 1
• 239000000264 sodium ferrocyanide Substances 0.000 description 1
• 235000012247 sodium ferrocyanide Nutrition 0.000 description 1
• GTSHREYGKSITGK-UHFFFAOYSA-N sodium ferrocyanide Chemical compound [Na+].[Na+].[Na+].[Na+].[Fe+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] GTSHREYGKSITGK-UHFFFAOYSA-N 0.000 description 1
• 229910052938 sodium sulfate Inorganic materials 0.000 description 1
• 235000011152 sodium sulphate Nutrition 0.000 description 1
• 230000001954 sterilising effect Effects 0.000 description 1
• 238000004659 sterilization and disinfection Methods 0.000 description 1
• 229960002423 tetracycline trihydrate Drugs 0.000 description 1