BE536231A

BE536231A -

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Publication number: BE536231A
Authority: BE; Belgium
Prior art keywords: tetracycline; chlortetracycline; water; solution; sep
Prior art date

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English (en)

French (fr)

Publication of BE536231A publication Critical patent/BE536231A/fr

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229960002180 Tetracycline Drugs 0.000 claims description 41
OFVLGDICTFRJMM-WESIUVDSSA-N Tetracycline 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)=C3C(=O)C2=C1O OFVLGDICTFRJMM-WESIUVDSSA-N 0.000 claims description 41
239000004098 Tetracycline Substances 0.000 claims description 41
235000019364 tetracycline Nutrition 0.000 claims description 41
229960004475 Chlortetracycline Drugs 0.000 claims description 30
DHPRQBPJLMKORJ-XRNKAMNCSA-N (4S,4aS,5aS,6S,12aR)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide 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)C3=C(O)C2=C1O DHPRQBPJLMKORJ-XRNKAMNCSA-N 0.000 claims description 29
235000019365 chlortetracycline Nutrition 0.000 claims description 29
239000004099 Chlortetracycline Substances 0.000 claims description 28
239000000243 solution Substances 0.000 claims description 26
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
230000003115 biocidal Effects 0.000 claims description 25
239000000203 mixture 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
239000003960 organic solvent Substances 0.000 claims description 15
229940064005 Antibiotic throat preparations Drugs 0.000 claims description 14
229940083879 Antibiotics FOR TREATMENT OF HEMORRHOIDS AND ANAL FISSURES FOR TOPICAL USE Drugs 0.000 claims description 14
229940042052 Antibiotics for systemic use Drugs 0.000 claims description 14
229940042786 Antitubercular Antibiotics Drugs 0.000 claims description 14
229940093922 Gynecological Antibiotics Drugs 0.000 claims description 14
229940024982 Topical Antifungal Antibiotics Drugs 0.000 claims description 14
239000003242 anti bacterial agent Substances 0.000 claims description 14
229940079866 intestinal antibiotics Drugs 0.000 claims description 14
229940005935 ophthalmologic Antibiotics Drugs 0.000 claims description 14
239000000284 extract Substances 0.000 claims description 13
238000000034 method Methods 0.000 claims description 12
239000011780 sodium chloride Substances 0.000 claims description 12
150000003839 salts Chemical class 0.000 claims description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl 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
229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 description 22
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
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
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
239000002585 base Substances 0.000 description 4
238000010531 catalytic reduction reaction Methods 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
239000000126 substance Substances 0.000 description 4
239000002253 acid 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
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 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
VBIXEXWLHSRNKB-UHFFFAOYSA-N Ammonium oxalate Chemical compound [NH4+].[NH4+].[O-]C(=O)C([O-])=O VBIXEXWLHSRNKB-UHFFFAOYSA-N 0.000 description 2
235000010469 Glycine max Nutrition 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N Isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
241000187747 Streptomyces Species 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating Effects 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
239000002021 butanolic extract Substances 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
230000020477 pH reduction Effects 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
239000000276 potassium ferrocyanide Substances 0.000 description 2
OCPOWIWGGAATRP-UHFFFAOYSA-N potassium hexacyanoferrate(4-) Chemical compound [K+].[K+].[K+].[K+].N#C[Fe-4](C#N)(C#N)(C#N)(C#N)C#N OCPOWIWGGAATRP-UHFFFAOYSA-N 0.000 description 2
150000003242 quaternary ammonium salts Chemical class 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000007787 solid Substances 0.000 description 2
210000004215 spores Anatomy 0.000 description 2
ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-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
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
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
ZSIAUFGUXNUGDI-UHFFFAOYSA-N 1-Hexanol Chemical class CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
BFNBIHQBYMNNAN-UHFFFAOYSA-N Ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate dianion Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
240000007842 Glycine max Species 0.000 description 1
241000186984 Kitasatospora aureofaciens Species 0.000 description 1
230000036740 Metabolism Effects 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
240000004808 Saccharomyces cerevisiae Species 0.000 description 1
229960002423 TETRACYCLINE TRIHYDRATE Drugs 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
238000007792 addition Methods 0.000 description 1
238000005273 aeration Methods 0.000 description 1
239000008272 agar Substances 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
QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
229910052921 ammonium sulfate Inorganic materials 0.000 description 1
235000011130 ammonium sulphate Nutrition 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L cacl2 Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
235000012970 cakes Nutrition 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
BHPQYMZQTOCNFJ-UHFFFAOYSA-N calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride 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
230000005712 crystallization Effects 0.000 description 1
JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecan-1-amine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 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
230000000977 initiatory Effects 0.000 description 1
239000002054 inoculum Substances 0.000 description 1
AHEVKYYGXVEWNO-UEPZRUIBSA-N lymecycline Chemical compound C1=CC=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(O)=C(C(=O)NCNCCCC[C@H](N)C(O)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O AHEVKYYGXVEWNO-UEPZRUIBSA-N 0.000 description 1
238000005259 measurement Methods 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
230000035786 metabolism 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
230000004048 modification Effects 0.000 description 1
238000006011 modification reaction Methods 0.000 description 1
QDHHCQZDFGDHMP-UHFFFAOYSA-N monochloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 1
AMQJEAYHLZJPGS-UHFFFAOYSA-N n-pentanol Chemical class CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
230000001264 neutralization Effects 0.000 description 1
230000003472 neutralizing Effects 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 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 Effects 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000000746 purification Methods 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
OBOWFEZVRNRJBU-UHFFFAOYSA-N sodium hexacyanoferrate(4-) Chemical compound [Na+].[Na+].[Na+].[Na+].N#C[Fe-4](C#N)(C#N)(C#N)(C#N)C#N OBOWFEZVRNRJBU-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 Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1