BE556395A - - Google Patents

Info

Publication number

BE556395A

BE556395A BE556395DA BE556395A BE 556395 A BE556395 A BE 556395A BE 556395D A BE556395D A BE 556395DA BE 556395 A BE556395 A BE 556395A

Authority

BE

Belgium

Prior art keywords

tetracycline

neutral

solution

added

filtered

Prior art date

Links

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• 229960002180 Tetracycline Drugs 0.000 claims description 25
• 239000004098 Tetracycline Substances 0.000 claims description 25
• OFVLGDICTFRJMM-WESIUVDSSA-N Tetracycline Chemical group 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 25
• 235000019364 tetracycline Nutrition 0.000 claims description 25
• 230000001264 neutralization Effects 0.000 claims description 12
• 239000002002 slurry Substances 0.000 claims description 6
• 238000000034 method Methods 0.000 claims description 4
• 230000001225 therapeutic Effects 0.000 claims description 4
• LSNNMFCWUKXFEE-UHFFFAOYSA-L Sulphite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 claims description 3
• 239000000126 substance Substances 0.000 claims description 2
• 239000000243 solution Substances 0.000 description 10
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
• 239000000047 product Substances 0.000 description 8
• VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
• 239000000706 filtrate Substances 0.000 description 5
• 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 description 4
• PQUCIEFHOVEZAU-UHFFFAOYSA-N Ammonium sulfite Chemical compound [NH4+].[NH4+].[O-]S([O-])=O PQUCIEFHOVEZAU-UHFFFAOYSA-N 0.000 description 4
• 239000003513 alkali Substances 0.000 description 4
• 239000008367 deionised water Substances 0.000 description 4
• 239000000203 mixture Substances 0.000 description 4
• GEHJYWRUCIMESM-UHFFFAOYSA-L Sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 3
• 239000012065 filter cake Substances 0.000 description 3
• 239000000463 material Substances 0.000 description 3
• 239000000725 suspension Substances 0.000 description 3
• 235000020357 syrup Nutrition 0.000 description 3
• 239000006188 syrup Substances 0.000 description 3
• 239000005909 Kieselgur Substances 0.000 description 2
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
• FKHIFSZMMVMEQY-UHFFFAOYSA-N Talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 2
• 239000007864 aqueous solution Substances 0.000 description 2
• 235000019658 bitter taste Nutrition 0.000 description 2
• 238000000855 fermentation Methods 0.000 description 2
• 230000004151 fermentation Effects 0.000 description 2
• 239000007788 liquid Substances 0.000 description 2
• 239000000391 magnesium silicate Substances 0.000 description 2
• 229910052919 magnesium silicate Inorganic materials 0.000 description 2
• 235000019792 magnesium silicate Nutrition 0.000 description 2
• 244000005700 microbiome Species 0.000 description 2
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
• 239000000825 pharmaceutical preparation Substances 0.000 description 2
• 238000002360 preparation method Methods 0.000 description 2
• 238000006042 reductive dechlorination reaction Methods 0.000 description 2
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
• 238000003756 stirring Methods 0.000 description 2
• ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 2
• YCIHPQHVWDULOY-FMZCEJRJSA-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;hydrochloride Chemical compound Cl.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 YCIHPQHVWDULOY-FMZCEJRJSA-N 0.000 description 1
• ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-Ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
• 229940093475 2-ethoxyethanol Drugs 0.000 description 1
• 241000219495 Betulaceae Species 0.000 description 1
• 229960004475 Chlortetracycline Drugs 0.000 description 1
• 239000004099 Chlortetracycline Substances 0.000 description 1
• 235000005979 Citrus limon Nutrition 0.000 description 1
• 240000002268 Citrus limon Species 0.000 description 1
• 239000002253 acid Substances 0.000 description 1
• 150000007513 acids Chemical class 0.000 description 1
• 150000001408 amides Chemical class 0.000 description 1
• 229940101006 anhydrous sodium sulfite Drugs 0.000 description 1
• LSNNMFCWUKXFEE-UHFFFAOYSA-M bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
• 239000002775 capsule Substances 0.000 description 1
• 239000003054 catalyst Substances 0.000 description 1
• 238000010531 catalytic reduction reaction Methods 0.000 description 1
• 239000003518 caustics Substances 0.000 description 1
• 239000003153 chemical reaction reagent Substances 0.000 description 1
• 235000019365 chlortetracycline Nutrition 0.000 description 1
• 230000001747 exhibiting Effects 0.000 description 1
• 238000007327 hydrogenolysis reaction Methods 0.000 description 1
• 239000012535 impurity Substances 0.000 description 1
• 238000004519 manufacturing process Methods 0.000 description 1
• 239000002674 ointment Substances 0.000 description 1
• 229910052763 palladium Inorganic materials 0.000 description 1
• 239000002244 precipitate Substances 0.000 description 1
• 239000012264 purified product Substances 0.000 description 1
• 230000002829 reduced Effects 0.000 description 1
• KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
• 239000011734 sodium Substances 0.000 description 1
• 229910052708 sodium Inorganic materials 0.000 description 1
• 235000010265 sodium sulphite Nutrition 0.000 description 1
• 239000010902 straw Substances 0.000 description 1
• 239000003826 tablet Substances 0.000 description 1
• 229960004989 tetracycline hydrochloride Drugs 0.000 description 1
• 230000000007 visual effect Effects 0.000 description 1