BE536015A

BE536015A -

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Publication number: BE536015A
Authority: BE; Belgium
Prior art keywords: antibiotic; tetracycline; solution; magnesium; barium
Prior art date

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English (en)

French (fr)

Publication of BE536015A publication Critical patent/BE536015A/fr

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230000003115 biocidal effect Effects 0.000 claims description 51
229910052751 metal Inorganic materials 0.000 claims description 34
239000002184 metal Substances 0.000 claims description 34
150000002739 metals Chemical class 0.000 claims description 26
239000000243 solution Substances 0.000 claims description 25
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
IWVCMVBTMGNXQD-PXOLEDIWSA-N oxytetracycline 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)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-PXOLEDIWSA-N 0.000 claims description 20
229930101283 tetracycline Natural products 0.000 claims description 20
239000004100 Oxytetracycline Substances 0.000 claims description 19
239000004098 Tetracycline Substances 0.000 claims description 19
229960000625 oxytetracycline Drugs 0.000 claims description 19
235000019366 oxytetracycline Nutrition 0.000 claims description 19
IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 claims description 19
229960002180 tetracycline Drugs 0.000 claims description 19
235000019364 tetracycline Nutrition 0.000 claims description 19
150000003522 tetracyclines Chemical class 0.000 claims description 19
239000003242 anti bacterial agent Substances 0.000 claims description 18
238000000034 method Methods 0.000 claims description 18
238000000855 fermentation Methods 0.000 claims description 16
230000004151 fermentation Effects 0.000 claims description 16
239000000203 mixture Substances 0.000 claims description 15
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 14
229910052749 magnesium Inorganic materials 0.000 claims description 14
239000011777 magnesium Substances 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 14
239000007864 aqueous solution Substances 0.000 claims description 12
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 12
229960004475 chlortetracycline Drugs 0.000 claims description 12
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 12
235000019365 chlortetracycline Nutrition 0.000 claims description 12
239000004099 Chlortetracycline Substances 0.000 claims description 11
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 10
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 10
229910052791 calcium Inorganic materials 0.000 claims description 10
239000011575 calcium Substances 0.000 claims description 10
229910052788 barium Inorganic materials 0.000 claims description 9
238000001914 filtration Methods 0.000 claims description 9
229940072172 tetracycline antibiotic Drugs 0.000 claims description 9
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
229910052790 beryllium Inorganic materials 0.000 claims description 3
ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 claims description 3
229910052793 cadmium Inorganic materials 0.000 claims description 3
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims description 3
238000012258 culturing Methods 0.000 claims description 3
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 3
229910052753 mercury Inorganic materials 0.000 claims description 3
235000015097 nutrients Nutrition 0.000 claims description 3
230000000737 periodic effect Effects 0.000 claims description 3
229910052712 strontium Inorganic materials 0.000 claims description 3
CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 claims description 3
229910052725 zinc Inorganic materials 0.000 claims description 3
239000011701 zinc Substances 0.000 claims description 3
150000002500 ions Chemical class 0.000 claims description 2
230000000704 physical effect Effects 0.000 claims 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
229910021645 metal ion Inorganic materials 0.000 description 24
239000002244 precipitate Substances 0.000 description 20
235000010633 broth Nutrition 0.000 description 19
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
229940088710 antibiotic agent Drugs 0.000 description 13
150000001875 compounds Chemical class 0.000 description 12
229940091250 magnesium supplement Drugs 0.000 description 11
238000001556 precipitation Methods 0.000 description 11
239000007787 solid Substances 0.000 description 7
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
150000002736 metal compounds Chemical class 0.000 description 6
239000000047 product Substances 0.000 description 6
230000001376 precipitating effect Effects 0.000 description 5
241001465754 Metazoa Species 0.000 description 4
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 3
239000005909 Kieselgur Substances 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
239000003929 acidic solution Substances 0.000 description 3
PWHCIQQGOQTFAE-UHFFFAOYSA-L barium chloride dihydrate Chemical compound O.O.[Cl-].[Cl-].[Ba+2] PWHCIQQGOQTFAE-UHFFFAOYSA-L 0.000 description 3
159000000009 barium salts Chemical class 0.000 description 3
239000001110 calcium chloride Substances 0.000 description 3
229910001628 calcium chloride Inorganic materials 0.000 description 3
239000012065 filter cake Substances 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
229940050906 magnesium chloride hexahydrate Drugs 0.000 description 3
DHRRIBDTHFBPNG-UHFFFAOYSA-L magnesium dichloride hexahydrate Chemical compound O.O.O.O.O.O.[Mg+2].[Cl-].[Cl-] DHRRIBDTHFBPNG-UHFFFAOYSA-L 0.000 description 3
239000000463 material Substances 0.000 description 3
244000005700 microbiome Species 0.000 description 3
230000008635 plant growth Effects 0.000 description 3
238000000926 separation method Methods 0.000 description 3
238000003756 stirring Methods 0.000 description 3
238000005406 washing Methods 0.000 description 3
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000012984 antibiotic solution Substances 0.000 description 2
IJBYNGRZBZDSDK-UHFFFAOYSA-N barium magnesium Chemical compound [Mg].[Ba] IJBYNGRZBZDSDK-UHFFFAOYSA-N 0.000 description 2
SHLNMHIRQGRGOL-UHFFFAOYSA-N barium zinc Chemical compound [Zn].[Ba] SHLNMHIRQGRGOL-UHFFFAOYSA-N 0.000 description 2
230000004071 biological effect Effects 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
ZFXVRMSLJDYJCH-UHFFFAOYSA-N calcium magnesium Chemical compound [Mg].[Ca] ZFXVRMSLJDYJCH-UHFFFAOYSA-N 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000003814 drug Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000012535 impurity Substances 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
159000000003 magnesium salts Chemical class 0.000 description 2
239000012265 solid product Substances 0.000 description 2
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 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
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 1
241000187747 Streptomyces Species 0.000 description 1
241000187419 Streptomyces rimosus Species 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
FQNGWRSKYZLJDK-UHFFFAOYSA-N [Ca].[Ba] Chemical compound [Ca].[Ba] FQNGWRSKYZLJDK-UHFFFAOYSA-N 0.000 description 1
238000010306 acid treatment Methods 0.000 description 1
238000013019 agitation Methods 0.000 description 1
239000003513 alkali Substances 0.000 description 1
239000002269 analeptic agent Substances 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
239000003899 bactericide agent Substances 0.000 description 1
150000003842 bromide salts Chemical class 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
239000001175 calcium sulphate Substances 0.000 description 1
235000011132 calcium sulphate Nutrition 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000005018 casein Substances 0.000 description 1
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 description 1
235000021240 caseins Nutrition 0.000 description 1
XMEVHPAGJVLHIG-FMZCEJRJSA-N chembl454950 Chemical compound [Cl-].C1=CC=C2[C@](O)(C)[C@H]3C[C@H]4[C@H]([NH+](C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O XMEVHPAGJVLHIG-FMZCEJRJSA-N 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
239000007952 growth promoter Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000012264 purified product Substances 0.000 description 1
239000002994 raw material Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011343 solid material Substances 0.000 description 1
239000012086 standard solution Substances 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
229960004989 tetracycline hydrochloride Drugs 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1