BE557870A

BE557870A -

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Publication number: BE557870A
Authority: BE; Belgium
Prior art keywords: sep; demethyltetracycline; chlorodemethyltetracycline; antibiotics; medium
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English (en)

French (fr)

Publication of BE557870A publication Critical patent/BE557870A/fr

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RMVMLZHPWMTQGK-SOUFLCLCSA-N (4s,4as,5as,6s,12ar)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1([C@H]2O)=CC=CC(O)=C1C(O)=C1[C@@H]2C[C@H]2[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]2(O)C1=O RMVMLZHPWMTQGK-SOUFLCLCSA-N 0.000 claims description 46
239000003242 anti bacterial agent Substances 0.000 claims description 45
229940088710 antibiotic agent Drugs 0.000 claims description 44
JCSGAUKCDAVARS-UHFFFAOYSA-N demethyltetracycline Natural products CN(C1C(=C(C(C2(C(=C3C(C4=C(C=CC=C4C(C3CC12)O)O)=O)O)O)=O)C(=O)N)O)C JCSGAUKCDAVARS-UHFFFAOYSA-N 0.000 claims description 40
239000000203 mixture Substances 0.000 claims description 29
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238000000034 method Methods 0.000 claims description 28
230000008569 process Effects 0.000 claims description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 11
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 10
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150000003839 salts Chemical class 0.000 claims description 9
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238000002360 preparation method Methods 0.000 claims description 7
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
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150000002500 ions Chemical class 0.000 claims description 3
230000001225 therapeutic effect Effects 0.000 claims description 2
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150000001342 alkaline earth metals Chemical class 0.000 claims 1
238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
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229910052763 palladium Inorganic materials 0.000 claims 1
239000004098 Tetracycline Substances 0.000 description 52
235000019364 tetracycline Nutrition 0.000 description 52
150000003522 tetracyclines Chemical class 0.000 description 52
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 38
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 description 36
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 description 36
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239000002609 medium Substances 0.000 description 34
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LJVDOBHBFMLPMI-XRNKAMNCSA-N (4s,4as,5as,6s,12ar)-7-bromo-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide Chemical compound C1=CC(Br)=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 LJVDOBHBFMLPMI-XRNKAMNCSA-N 0.000 description 7
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BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
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239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000012521 purified sample Substances 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical group [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Inorganic materials [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
241000894007 species Species 0.000 description 1
238000002798 spectrophotometry method Methods 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
229910052712 strontium Inorganic materials 0.000 description 1
CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical class [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000000725 suspension Substances 0.000 description 1
235000012976 tarts Nutrition 0.000 description 1
229940072172 tetracycline antibiotic Drugs 0.000 description 1
229960004989 tetracycline hydrochloride Drugs 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
150000004684 trihydrates Chemical class 0.000 description 1
238000002211 ultraviolet spectrum Methods 0.000 description 1
239000001052 yellow pigment Substances 0.000 description 1
229910000368 zinc sulfate Inorganic materials 0.000 description 1
RZLVQBNCHSJZPX-UHFFFAOYSA-L zinc sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Zn+2].[O-]S([O-])(=O)=O RZLVQBNCHSJZPX-UHFFFAOYSA-L 0.000 description 1
229910052726 zirconium Inorganic materials 0.000 description 1