BE566261A

BE566261A -

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Publication number: BE566261A
Authority: BE; Belgium
Prior art keywords: novobiocin; benzene; mixture; sodium methoxide; sep
Prior art date

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English (en)

French (fr)

Publication of BE566261A publication Critical patent/BE566261A/fr

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UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 78
229960002950 novobiocin Drugs 0.000 claims description 52
YJQPYGGHQPGBLI-UHFFFAOYSA-N Novobiocin Natural products O1C(C)(C)C(OC)C(OC(N)=O)C(O)C1OC1=CC=C(C(O)=C(NC(=O)C=2C=C(CC=C(C)C)C(O)=CC=2)C(=O)O2)C2=C1C YJQPYGGHQPGBLI-UHFFFAOYSA-N 0.000 claims description 51
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 48
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 42
239000000243 solution Substances 0.000 claims description 32
239000000203 mixture Substances 0.000 claims description 29
238000000034 method Methods 0.000 claims description 28
230000002378 acidificating effect Effects 0.000 claims description 18
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
239000002904 solvent Substances 0.000 claims description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
WWPRGAYLRGSOSU-RNROJPEYSA-M Novobiocin sodium Chemical compound [Na+].O1C(C)(C)[C@H](OC)[C@@H](OC(N)=O)[C@@H](O)[C@@H]1OC1=CC=C(C([O-])=C(NC(=O)C=2C=C(CC=C(C)C)C(O)=CC=2)C(=O)O2)C2=C1C WWPRGAYLRGSOSU-RNROJPEYSA-M 0.000 claims description 12
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 12
238000003756 stirring Methods 0.000 claims description 11
239000002253 acid Substances 0.000 claims description 10
239000013078 crystal Substances 0.000 claims description 10
239000003849 aromatic solvent Substances 0.000 claims description 9
238000002425 crystallisation Methods 0.000 claims description 7
230000008025 crystallization Effects 0.000 claims description 7
238000001914 filtration Methods 0.000 claims description 7
239000003960 organic solvent Substances 0.000 claims description 6
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 5
239000012047 saturated solution Substances 0.000 claims description 5
239000008096 xylene Substances 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 3
238000006243 chemical reaction Methods 0.000 claims description 3
238000001035 drying Methods 0.000 claims description 3
YJQPYGGHQPGBLI-KGSXXDOSSA-N novobiocin Chemical compound O1C(C)(C)[C@H](OC)[C@@H](OC(N)=O)[C@@H](O)[C@@H]1OC1=CC=C(C(O)=C(NC(=O)C=2C=C(CC=C(C)C)C(O)=CC=2)C(=O)O2)C2=C1C YJQPYGGHQPGBLI-KGSXXDOSSA-N 0.000 claims 12
238000004090 dissolution Methods 0.000 claims 2
238000005406 washing Methods 0.000 claims 2
RXXCIBALSKQCAE-UHFFFAOYSA-N 3-methylbutoxymethylbenzene Chemical compound CC(C)CCOCC1=CC=CC=C1 RXXCIBALSKQCAE-UHFFFAOYSA-N 0.000 claims 1
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims 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 claims 1
150000001768 cations Chemical class 0.000 claims 1
229910052708 sodium Inorganic materials 0.000 claims 1
239000011734 sodium Substances 0.000 claims 1
YJQPYGGHQPGBLI-KGSXXDOSSA-M novobiocin(1-) Chemical compound O1C(C)(C)[C@H](OC)[C@@H](OC(N)=O)[C@@H](O)[C@@H]1OC1=CC=C(C([O-])=C(NC(=O)C=2C=C(CC=C(C)C)C(O)=CC=2)C(=O)O2)C2=C1C YJQPYGGHQPGBLI-KGSXXDOSSA-M 0.000 description 38
239000000047 product Substances 0.000 description 11
239000007787 solid Substances 0.000 description 11
235000010633 broth Nutrition 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
239000011877 solvent mixture Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000002609 medium Substances 0.000 description 6
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
230000003115 biocidal effect Effects 0.000 description 5
239000012065 filter cake Substances 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
239000005909 Kieselgur Substances 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
239000012736 aqueous medium Substances 0.000 description 3
239000008121 dextrose Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000000284 extract Substances 0.000 description 3
238000000855 fermentation Methods 0.000 description 3
230000004151 fermentation Effects 0.000 description 3
239000008187 granular material Substances 0.000 description 3
239000012535 impurity Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
229920001817 Agar Polymers 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
235000010469 Glycine max Nutrition 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
241001454746 Streptomyces niveus Species 0.000 description 2
238000013019 agitation Methods 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
235000015278 beef Nutrition 0.000 description 2
239000002021 butanolic extract Substances 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
235000013312 flour Nutrition 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
235000011121 sodium hydroxide Nutrition 0.000 description 2
239000002689 soil Substances 0.000 description 2
239000007921 spray Substances 0.000 description 2
229910001220 stainless steel Inorganic materials 0.000 description 2
239000010935 stainless steel Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
208000035143 Bacterial infection Diseases 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
244000068988 Glycine max Species 0.000 description 1
239000007836 KH2PO4 Substances 0.000 description 1
229930182555 Penicillin Natural products 0.000 description 1
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
241000364057 Peoria Species 0.000 description 1
244000046052 Phaseolus vulgaris Species 0.000 description 1
235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
241000295644 Staphylococcaceae Species 0.000 description 1
241000187747 Streptomyces Species 0.000 description 1
241000153282 Theope Species 0.000 description 1
241000194062 Xanthomonas phaseoli Species 0.000 description 1
238000003916 acid precipitation Methods 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000011149 active material Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
230000002411 adverse Effects 0.000 description 1
238000005273 aeration Methods 0.000 description 1
238000010564 aerobic fermentation Methods 0.000 description 1
239000008272 agar Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000002518 antifoaming agent Substances 0.000 description 1
208000022362 bacterial infectious disease Diseases 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
WVHBHPATSLQXGC-UHFFFAOYSA-N benzene;ethanol Chemical compound CCO.C1=CC=CC=C1 WVHBHPATSLQXGC-UHFFFAOYSA-N 0.000 description 1
KSTSKZBJCVLLKS-UHFFFAOYSA-N benzene;propan-2-ol Chemical compound CC(C)O.C1=CC=CC=C1 KSTSKZBJCVLLKS-UHFFFAOYSA-N 0.000 description 1
230000000975 bioactive effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229940041514 candida albicans extract Drugs 0.000 description 1
239000002775 capsule Substances 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
229920002301 cellulose acetate Polymers 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
238000012258 culturing Methods 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000009826 distribution Methods 0.000 description 1
-1 ethanol or propanol Chemical compound 0.000 description 1
239000000469 ethanolic extract Substances 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012530 fluid Substances 0.000 description 1
235000011389 fruit/vegetable juice Nutrition 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
239000011521 glass Substances 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
229910052742 iron Inorganic materials 0.000 description 1
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
125000005647 linker group Chemical group 0.000 description 1
235000020094 liqueur Nutrition 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
JZMYRQHKOYJYQO-UHFFFAOYSA-N methanol;1,2-xylene Chemical group OC.CC1=CC=CC=C1C JZMYRQHKOYJYQO-UHFFFAOYSA-N 0.000 description 1
BKBMACKZOSMMGT-UHFFFAOYSA-N methanol;toluene Chemical compound OC.CC1=CC=CC=C1 BKBMACKZOSMMGT-UHFFFAOYSA-N 0.000 description 1
244000005700 microbiome Species 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
235000019796 monopotassium phosphate Nutrition 0.000 description 1
231100000989 no adverse effect Toxicity 0.000 description 1
229960004781 novobiocin sodium Drugs 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
XNGIFLGASWRNHJ-UHFFFAOYSA-M phthalate(1-) Chemical compound OC(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-M 0.000 description 1
229910052573 porcelain Inorganic materials 0.000 description 1
GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
238000011084 recovery Methods 0.000 description 1
239000013557 residual solvent Substances 0.000 description 1
210000002345 respiratory system Anatomy 0.000 description 1
239000002002 slurry Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
OTNVGWMVOULBFZ-UHFFFAOYSA-N sodium;hydrochloride Chemical compound [Na].Cl OTNVGWMVOULBFZ-UHFFFAOYSA-N 0.000 description 1
239000011343 solid material Substances 0.000 description 1
241000894007 species Species 0.000 description 1
230000028070 sporulation Effects 0.000 description 1
238000003892 spreading Methods 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000011800 void material Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000012138 yeast extract Substances 0.000 description 1