BE562073A - - Google Patents

Info

Publication number

BE562073A

BE562073A BE562073DA BE562073A BE 562073 A BE562073 A BE 562073A BE 562073D A BE562073D A BE 562073DA BE 562073 A BE562073 A BE 562073A

Authority

BE

Belgium

Prior art keywords

sep

tetracycline

process according

chlorination

inhibitor

Prior art date

1956-11-02

Links

• Espacenet
• Global Dossier
• Discuss

• 229960002180 tetracycline Drugs 0.000 claims description 27
• 229930101283 tetracycline Natural products 0.000 claims description 27
• 239000004098 Tetracycline Substances 0.000 claims description 26
• 235000019364 tetracycline Nutrition 0.000 claims description 26
• 150000003522 tetracyclines Chemical class 0.000 claims description 26
• 238000000855 fermentation Methods 0.000 claims description 25
• 230000004151 fermentation Effects 0.000 claims description 25
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 22
• 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 claims description 19
• 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 claims description 19
• 239000003112 inhibitor Substances 0.000 claims description 19
• 238000005660 chlorination reaction Methods 0.000 claims description 16
• 244000005700 microbiome Species 0.000 claims description 14
• 238000000034 method Methods 0.000 claims description 12
• 238000002360 preparation method Methods 0.000 claims description 7
• -1 benzyl N-acetyl-dithiocarbazate Chemical group 0.000 claims description 5
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
• 239000000126 substance Substances 0.000 claims description 5
• 241000187747 Streptomyces Species 0.000 claims description 4
• 125000000217 alkyl group Chemical group 0.000 claims description 4
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
• 239000000463 material Substances 0.000 claims description 3
• 239000002609 medium Substances 0.000 claims 2
• 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 1
• HLKIEZNVCBRNSO-UHFFFAOYSA-N NN(C=O)C(SCC1=CC=CC=C1)=S Chemical group NN(C=O)C(SCC1=CC=CC=C1)=S HLKIEZNVCBRNSO-UHFFFAOYSA-N 0.000 claims 1
• 238000010564 aerobic fermentation Methods 0.000 claims 1
• 150000001412 amines Chemical class 0.000 claims 1
• 239000012736 aqueous medium Substances 0.000 claims 1
• 239000007864 aqueous solution Substances 0.000 claims 1
• 239000012990 dithiocarbamate Substances 0.000 claims 1
• 230000015572 biosynthetic process Effects 0.000 description 9
• 235000015097 nutrients Nutrition 0.000 description 8
• 240000008042 Zea mays Species 0.000 description 6
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 6
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
• VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
• 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 4
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
• 150000001805 chlorine compounds Chemical class 0.000 description 4
• 150000001875 compounds Chemical class 0.000 description 4
• 235000005822 corn Nutrition 0.000 description 4
• 238000002803 maceration Methods 0.000 description 4
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
• 241000894007 species Species 0.000 description 4
• 238000003786 synthesis reaction Methods 0.000 description 4
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
• 241000186984 Kitasatospora aureofaciens Species 0.000 description 3
• 230000008901 benefit Effects 0.000 description 3
• 230000003115 biocidal effect Effects 0.000 description 3
• 239000000470 constituent Substances 0.000 description 3
• 230000000694 effects Effects 0.000 description 3
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
• 102000016736 Cyclin Human genes 0.000 description 2
• 108050006400 Cyclin Proteins 0.000 description 2
• 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 2
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
• NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 description 2
• 241000282320 Panthera leo Species 0.000 description 2
• 241001637516 Polygonia c-album Species 0.000 description 2
• 229920002472 Starch Polymers 0.000 description 2
• 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 2
• 235000019270 ammonium chloride Nutrition 0.000 description 2
• BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
• 229910052921 ammonium sulfate Inorganic materials 0.000 description 2
• 235000011130 ammonium sulphate Nutrition 0.000 description 2
• 239000003242 anti bacterial agent Substances 0.000 description 2
• 229940088710 antibiotic agent Drugs 0.000 description 2
• WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
• 229910000019 calcium carbonate Inorganic materials 0.000 description 2
• 235000010216 calcium carbonate Nutrition 0.000 description 2
• 230000007423 decrease Effects 0.000 description 2
• 235000013312 flour Nutrition 0.000 description 2
• 239000002054 inoculum Substances 0.000 description 2
• 239000003456 ion exchange resin Substances 0.000 description 2
• 229920003303 ion-exchange polymer Polymers 0.000 description 2
• 235000009973 maize Nutrition 0.000 description 2
• 239000002994 raw material Substances 0.000 description 2
• 238000011084 recovery Methods 0.000 description 2
• 150000003839 salts Chemical class 0.000 description 2
• 239000008107 starch Substances 0.000 description 2
• 235000019698 starch Nutrition 0.000 description 2
• 229940072172 tetracycline antibiotic Drugs 0.000 description 2
• 231100000331 toxic Toxicity 0.000 description 2
• 230000002588 toxic effect Effects 0.000 description 2
• 235000017060 Arachis glabrata Nutrition 0.000 description 1
• 244000105624 Arachis hypogaea Species 0.000 description 1
• 235000010777 Arachis hypogaea Nutrition 0.000 description 1
• 235000018262 Arachis monticola Nutrition 0.000 description 1
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
• 239000004099 Chlortetracycline Substances 0.000 description 1
• 241000581364 Clinitrachus argentatus Species 0.000 description 1
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
• BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
• RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
• JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
• 235000019733 Fish meal Nutrition 0.000 description 1
• 239000001888 Peptone Substances 0.000 description 1
• 108010080698 Peptones Proteins 0.000 description 1
• 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
• 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 1
• BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
• 229910021607 Silver chloride Inorganic materials 0.000 description 1
• 235000019764 Soybean Meal Nutrition 0.000 description 1
• 101100073357 Streptomyces halstedii sch2 gene Proteins 0.000 description 1
• 241000811234 Streptomyces sayamaensis Species 0.000 description 1
• 241000231756 Streptomyces viridifaciens Species 0.000 description 1
• 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 1
• 229930006000 Sucrose Natural products 0.000 description 1
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
• 238000005273 aeration Methods 0.000 description 1
• 125000003277 amino group Chemical group 0.000 description 1
• 239000001166 ammonium sulphate Substances 0.000 description 1
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 239000004202 carbamide Substances 0.000 description 1
• 235000013877 carbamide Nutrition 0.000 description 1
• 239000003795 chemical substances by application Substances 0.000 description 1
• 239000000460 chlorine Substances 0.000 description 1
• 229910052801 chlorine Inorganic materials 0.000 description 1
• 229960004475 chlortetracycline Drugs 0.000 description 1
• 235000019365 chlortetracycline Nutrition 0.000 description 1
• 239000010941 cobalt Substances 0.000 description 1
• 229910017052 cobalt Inorganic materials 0.000 description 1
• GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
• 229910052802 copper Inorganic materials 0.000 description 1
• 239000010949 copper Substances 0.000 description 1
• 239000008121 dextrose Substances 0.000 description 1
• OAEGRYMCJYIXQT-UHFFFAOYSA-N dithiooxamide Chemical compound NC(=S)C(N)=S OAEGRYMCJYIXQT-UHFFFAOYSA-N 0.000 description 1
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
• 239000000284 extract Substances 0.000 description 1
• 239000004467 fishmeal Substances 0.000 description 1
• 239000007789 gas Substances 0.000 description 1
• 239000008103 glucose Substances 0.000 description 1
• 235000001727 glucose Nutrition 0.000 description 1
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
• RWSOTUBLDIXVET-UHFFFAOYSA-M hydrosulfide Chemical compound [SH-] RWSOTUBLDIXVET-UHFFFAOYSA-M 0.000 description 1
• 230000002401 inhibitory effect Effects 0.000 description 1
• 238000011081 inoculation Methods 0.000 description 1
• 229910052500 inorganic mineral Inorganic materials 0.000 description 1
• 229910052742 iron Inorganic materials 0.000 description 1
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 239000010699 lard oil Substances 0.000 description 1
• 238000011031 large-scale manufacturing process Methods 0.000 description 1
• WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
• 238000004519 manufacturing process Methods 0.000 description 1
• 235000013372 meat Nutrition 0.000 description 1
• 239000011707 mineral Substances 0.000 description 1
• 235000010755 mineral Nutrition 0.000 description 1
• 239000000203 mixture Substances 0.000 description 1
• 235000013379 molasses Nutrition 0.000 description 1
• 230000000877 morphologic effect Effects 0.000 description 1
• 235000020232 peanut Nutrition 0.000 description 1
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
• 235000019319 peptone Nutrition 0.000 description 1
• 231100000614 poison Toxicity 0.000 description 1
• 230000007096 poisonous effect Effects 0.000 description 1
• 238000001556 precipitation Methods 0.000 description 1
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 238000009877 rendering Methods 0.000 description 1
• 229910052709 silver Inorganic materials 0.000 description 1
• 239000004332 silver Substances 0.000 description 1
• HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
• 239000004455 soybean meal Substances 0.000 description 1
• 230000001954 sterilising effect Effects 0.000 description 1
• 238000004659 sterilization and disinfection Methods 0.000 description 1
• 229960004793 sucrose Drugs 0.000 description 1
• 238000010408 sweeping Methods 0.000 description 1
• 239000011573 trace mineral Substances 0.000 description 1
• 235000013619 trace mineral Nutrition 0.000 description 1
• 239000011701 zinc Substances 0.000 description 1
• 229910052725 zinc Inorganic materials 0.000 description 1