BE530635A - - Google Patents

Info

Publication number

BE530635A

BE530635A BE530635DA BE530635A BE 530635 A BE530635 A BE 530635A BE 530635D A BE530635D A BE 530635DA BE 530635 A BE530635 A BE 530635A

Authority

BE

Belgium

Prior art keywords

omegamycin

sep

tetracycline

solution

preparation

Prior art date

Links

• Espacenet
• Global Dossier
• Discuss

• LRHPLDYGYMQRHN-UHFFFAOYSA-N Butanol Natural products CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 96
• 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 claims description 92
• 229930101283 tetracycline Natural products 0.000 claims description 76
• 239000004098 Tetracycline Substances 0.000 claims description 75
• 229960002180 tetracycline Drugs 0.000 claims description 75
• 235000019364 tetracycline Nutrition 0.000 claims description 75
• 150000003522 tetracyclines Chemical class 0.000 claims description 73
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 60
• 238000000034 method Methods 0.000 claims description 55
• 238000000855 fermentation Methods 0.000 claims description 49
• 230000004151 fermentation Effects 0.000 claims description 49
• 239000000243 solution Substances 0.000 claims description 46
• 239000007787 solid Substances 0.000 claims description 36
• 230000008569 process Effects 0.000 claims description 33
• 239000002253 acid Substances 0.000 claims description 28
• 239000000203 mixture Substances 0.000 claims description 26
• 238000002360 preparation method Methods 0.000 claims description 26
• 239000007864 aqueous solution Substances 0.000 claims description 25
• 239000002904 solvent Substances 0.000 claims description 25
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
• 241000187747 Streptomyces Species 0.000 claims description 24
• 230000003115 biocidal effect Effects 0.000 claims description 24
• 150000003839 salts Chemical class 0.000 claims description 22
• 230000000694 effects Effects 0.000 claims description 21
• 238000000605 extraction Methods 0.000 claims description 20
• 238000011161 development Methods 0.000 claims description 19
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 17
• 229920006395 saturated elastomer Polymers 0.000 claims description 15
• 235000015097 nutrients Nutrition 0.000 claims description 13
• 239000000126 substance Substances 0.000 claims description 13
• 230000000844 anti-bacterial effect Effects 0.000 claims description 12
• -1 bydrogen Chemical compound 0.000 claims description 11
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 11
• 238000000926 separation method Methods 0.000 claims description 11
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 10
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 10
• 230000001225 therapeutic effect Effects 0.000 claims description 10
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 10
• 208000035143 Bacterial infection Diseases 0.000 claims description 9
• 208000022362 bacterial infectious disease Diseases 0.000 claims description 9
• 150000001720 carbohydrates Chemical class 0.000 claims description 9
• 239000003960 organic solvent Substances 0.000 claims description 9
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
• 239000001509 sodium citrate Substances 0.000 claims description 8
• 238000001228 spectrum Methods 0.000 claims description 8
• 229960000583 acetic acid Drugs 0.000 claims description 7
• 229910052799 carbon Inorganic materials 0.000 claims description 7
• 241000894006 Bacteria Species 0.000 claims description 6
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
• 150000007513 acids Chemical class 0.000 claims description 6
• 239000002775 capsule Substances 0.000 claims description 6
• 239000007788 liquid Substances 0.000 claims description 6
• NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 5
• UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 5
• 229910052751 metal Inorganic materials 0.000 claims description 5
• 229910052757 nitrogen Inorganic materials 0.000 claims description 5
• 229940124531 pharmaceutical excipient Drugs 0.000 claims description 5
• 239000000377 silicon dioxide Substances 0.000 claims description 5
• 241000894007 species Species 0.000 claims description 5
• 150000001875 compounds Chemical class 0.000 claims description 4
• PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 claims description 4
• 239000002184 metal Substances 0.000 claims description 4
• 238000001556 precipitation Methods 0.000 claims description 4
• NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 claims description 4
• 238000005406 washing Methods 0.000 claims description 4
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
• 239000012362 glacial acetic acid Substances 0.000 claims description 3
• 150000002739 metals Chemical class 0.000 claims description 3
• 239000001301 oxygen Substances 0.000 claims description 3
• 229910052760 oxygen Inorganic materials 0.000 claims description 3
• 238000001179 sorption measurement Methods 0.000 claims description 3
• 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 claims description 2
• 239000004615 ingredient Substances 0.000 claims description 2
• 238000002844 melting Methods 0.000 claims description 2
• 230000008018 melting Effects 0.000 claims description 2
• 229960002423 tetracycline trihydrate Drugs 0.000 claims description 2
• 231100000252 nontoxic Toxicity 0.000 claims 2
• 230000003000 nontoxic effect Effects 0.000 claims 2
• 239000012439 solid excipient Substances 0.000 claims 2
• 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
• 235000010633 broth Nutrition 0.000 description 52
• 229920001817 Agar Polymers 0.000 description 36
• 239000008272 agar Substances 0.000 description 36
• 235000002639 sodium chloride Nutrition 0.000 description 28
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
• 239000002609 medium Substances 0.000 description 26
• 238000012360 testing method Methods 0.000 description 25
• 238000010790 dilution Methods 0.000 description 24
• 239000012895 dilution Substances 0.000 description 24
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
• 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 19
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
• 230000018109 developmental process Effects 0.000 description 18
• 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 16
• 238000001914 filtration Methods 0.000 description 15
• 239000002244 precipitate Substances 0.000 description 15
• 239000000049 pigment Substances 0.000 description 14
• 235000014469 Bacillus subtilis Nutrition 0.000 description 13
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
• 235000013312 flour Nutrition 0.000 description 12
• 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 description 12
• UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 11
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 11
• 239000001110 calcium chloride Substances 0.000 description 11
• 229910001628 calcium chloride Inorganic materials 0.000 description 11
• 235000011148 calcium chloride Nutrition 0.000 description 11
• 239000000047 product Substances 0.000 description 11
• 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 description 11
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
• VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 10
• BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 10
• 239000004100 Oxytetracycline Substances 0.000 description 10
• 239000000872 buffer Substances 0.000 description 10
• 229910001424 calcium ion Inorganic materials 0.000 description 10
• 229960000625 oxytetracycline Drugs 0.000 description 10
• 235000019366 oxytetracycline Nutrition 0.000 description 10
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
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• 235000010469 Glycine max Nutrition 0.000 description 8
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• 238000003556 assay Methods 0.000 description 7
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• 239000002585 base Substances 0.000 description 7
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• 239000000284 extract Substances 0.000 description 7
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 6
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
• 239000011575 calcium Substances 0.000 description 6
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• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
• 239000011780 sodium chloride Substances 0.000 description 6
• 235000011121 sodium hydroxide Nutrition 0.000 description 6
• 239000003826 tablet Substances 0.000 description 6
• 241000699666 Mus <mouse, genus> Species 0.000 description 5
• 229930006000 Sucrose Natural products 0.000 description 5
• CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 5
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• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
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• 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 4
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• POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
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• UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 4
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• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
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• AIUDWMLXCFRVDR-UHFFFAOYSA-N dimethyl 2-(3-ethyl-3-methylpentyl)propanedioate Chemical compound CCC(C)(CC)CCC(C(=O)OC)C(=O)OC AIUDWMLXCFRVDR-UHFFFAOYSA-N 0.000 description 3
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• VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 3
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• FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
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