CS207462B1 - method of making the antibiotics - Google Patents

method of making the antibiotics Download PDF

Info

Publication number: CS207462B1
Authority: CS; Czechoslovakia
Prior art keywords: antibiotic; column; ethyl acetate; methanol; mixture
Prior art date: 1976-06-30

Application number

CS425777A

Other languages

Czech (cs)

English (en)

Inventor

John H E J Martin

Martin R Hertz

Original Assignee

American Cyanamid Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1976-06-30

Filing date

1977-06-28

Publication date

1981-07-31

1977-06-28 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

1981-07-31 Publication of CS207462B1 publication Critical patent/CS207462B1/cs

Links

238000004519 manufacturing process Methods 0.000 title claims description 6
239000003242 anti bacterial agent Substances 0.000 title description 3
229940088710 antibiotic agent Drugs 0.000 title description 2
230000003115 biocidal effect Effects 0.000 claims abstract description 44
241000187391 Streptomyces hygroscopicus Species 0.000 claims abstract description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 8
238000000034 method Methods 0.000 claims description 5
229910052757 nitrogen Inorganic materials 0.000 claims description 5
150000001720 carbohydrates Chemical class 0.000 claims description 2
235000015097 nutrients Nutrition 0.000 claims description 2
238000000855 fermentation Methods 0.000 abstract description 11
230000004151 fermentation Effects 0.000 abstract description 11
229940124536 anticoccidial agent Drugs 0.000 abstract 1
239000003224 coccidiostatic agent Substances 0.000 abstract 1
230000002906 microbiologic effect Effects 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 61
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
239000000203 mixture Substances 0.000 description 25
241000287828 Gallus gallus Species 0.000 description 18
235000013330 chicken meat Nutrition 0.000 description 18
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 16
239000012071 phase Substances 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
239000002054 inoculum Substances 0.000 description 14
239000002609 medium Substances 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
239000005909 Kieselgur Substances 0.000 description 12
210000004215 spore Anatomy 0.000 description 12
235000005911 diet Nutrition 0.000 description 11
159000000000 sodium salts Chemical class 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
229920001817 Agar Polymers 0.000 description 9
239000002253 acid Substances 0.000 description 9
239000008272 agar Substances 0.000 description 9
230000037213 diet Effects 0.000 description 9
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 8
240000008042 Zea mays Species 0.000 description 7
235000002017 Zea mays subsp mays Nutrition 0.000 description 7
241000223932 Eimeria tenella Species 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
229910052799 carbon Inorganic materials 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
208000015181 infectious disease Diseases 0.000 description 6
238000011081 inoculation Methods 0.000 description 6
239000007788 liquid Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 5
241000223931 Eimeria acervulina Species 0.000 description 5
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 5
238000005273 aeration Methods 0.000 description 5
150000001768 cations Chemical class 0.000 description 5
235000005822 corn Nutrition 0.000 description 5
-1 d-raffinose Natural products 0.000 description 5
235000013312 flour Nutrition 0.000 description 5
239000011521 glass Substances 0.000 description 5
244000005700 microbiome Species 0.000 description 5
235000018102 proteins Nutrition 0.000 description 5
108090000623 proteins and genes Proteins 0.000 description 5
102000004169 proteins and genes Human genes 0.000 description 5
239000000243 solution Substances 0.000 description 5
238000001228 spectrum Methods 0.000 description 5
239000000126 substance Substances 0.000 description 5
238000012360 testing method Methods 0.000 description 5
238000004809 thin layer chromatography Methods 0.000 description 5
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
235000010469 Glycine max Nutrition 0.000 description 4
XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 description 4
238000000862 absorption spectrum Methods 0.000 description 4
235000011089 carbon dioxide Nutrition 0.000 description 4
239000012141 concentrate Substances 0.000 description 4
235000008504 concentrate Nutrition 0.000 description 4
239000000284 extract Substances 0.000 description 4
238000002156 mixing Methods 0.000 description 4
230000000877 morphologic effect Effects 0.000 description 4
238000012856 packing Methods 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
239000000049 pigment Substances 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000006188 syrup Substances 0.000 description 4
235000020357 syrup Nutrition 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
241000223924 Eimeria Species 0.000 description 3
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 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
241000187747 Streptomyces Species 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
238000010521 absorption reaction Methods 0.000 description 3
229940041514 candida albicans extract Drugs 0.000 description 3
239000013078 crystal Substances 0.000 description 3
239000002024 ethyl acetate extract Substances 0.000 description 3
238000002955 isolation Methods 0.000 description 3
239000000463 material Substances 0.000 description 3
230000011514 reflex Effects 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
230000028070 sporulation Effects 0.000 description 3
239000012138 yeast extract Substances 0.000 description 3
GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 2
GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
229920002261 Corn starch Polymers 0.000 description 2
241000499566 Eimeria brunetti Species 0.000 description 2
241000223934 Eimeria maxima Species 0.000 description 2
241000499563 Eimeria necatrix Species 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
244000068988 Glycine max Species 0.000 description 2
MJVAVZPDRWSRRC-UHFFFAOYSA-N Menadione Chemical compound C1=CC=C2C(=O)C(C)=CC(=O)C2=C1 MJVAVZPDRWSRRC-UHFFFAOYSA-N 0.000 description 2
229910002651 NO3 Inorganic materials 0.000 description 2
239000001888 Peptone Substances 0.000 description 2
108010080698 Peptones Proteins 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
235000001014 amino acid Nutrition 0.000 description 2
150000001413 amino acids Chemical class 0.000 description 2
239000007613 bennett's agar Substances 0.000 description 2
239000011575 calcium Substances 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
235000010216 calcium carbonate Nutrition 0.000 description 2
229910000019 calcium carbonate Inorganic materials 0.000 description 2
235000013339 cereals Nutrition 0.000 description 2
239000008120 corn starch Substances 0.000 description 2
229940099112 cornstarch Drugs 0.000 description 2
238000012258 culturing Methods 0.000 description 2
238000010908 decantation Methods 0.000 description 2
238000001514 detection method Methods 0.000 description 2
239000008121 dextrose Substances 0.000 description 2
230000000378 dietary effect Effects 0.000 description 2
238000004821 distillation Methods 0.000 description 2
238000001493 electron microscopy Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 description 2
210000001035 gastrointestinal tract Anatomy 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
239000008103 glucose Substances 0.000 description 2
238000011534 incubation Methods 0.000 description 2
235000009973 maize Nutrition 0.000 description 2
235000013336 milk Nutrition 0.000 description 2
239000008267 milk Substances 0.000 description 2
210000004080 milk Anatomy 0.000 description 2
150000002823 nitrates Chemical class 0.000 description 2
239000006877 oatmeal agar Substances 0.000 description 2
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
235000019319 peptone Nutrition 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000001965 potato dextrose agar Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
239000011877 solvent mixture Substances 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
239000011573 trace mineral Substances 0.000 description 2
235000013619 trace mineral Nutrition 0.000 description 2
UKIDUMMXBQMTKO-UHFFFAOYSA-N 1-methyl-1-nitro-2-nitrosoguanidine Chemical compound [O-][N+](=O)N(C)C(=N)NN=O UKIDUMMXBQMTKO-UHFFFAOYSA-N 0.000 description 1
FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 1
PYMYPHUHKUWMLA-UHFFFAOYSA-N 2,3,4,5-tetrahydroxypentanal Chemical compound OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 1
FKJSFKCZZIXQIP-UHFFFAOYSA-N 2-bromo-1-(4-bromophenyl)ethanone Chemical compound BrCC(=O)C1=CC=C(Br)C=C1 FKJSFKCZZIXQIP-UHFFFAOYSA-N 0.000 description 1
239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
241000271566 Aves Species 0.000 description 1
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
241000499489 Castor canadensis Species 0.000 description 1
GHOKWGTUZJEAQD-UHFFFAOYSA-N Chick antidermatitis factor Natural products OCC(C)(C)C(O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
235000019743 Choline chloride Nutrition 0.000 description 1
208000003495 Coccidiosis Diseases 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
AUNGANRZJHBGPY-UHFFFAOYSA-N D-Lyxoflavin Natural products OCC(O)C(O)C(O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-UHFFFAOYSA-N 0.000 description 1
239000004470 DL Methionine Substances 0.000 description 1
235000019733 Fish meal Nutrition 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
239000001828 Gelatine Substances 0.000 description 1
108010068370 Glutens Proteins 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
206010023076 Isosporiasis Diseases 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
240000004658 Medicago sativa Species 0.000 description 1
235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 1
235000011779 Menyanthes trifoliata Nutrition 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
OVBPIULPVIDEAO-UHFFFAOYSA-N N-Pteroyl-L-glutaminsaeure Natural products C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-UHFFFAOYSA-N 0.000 description 1
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
241000364057 Peoria Species 0.000 description 1
NGFMICBWJRZIBI-JZRPKSSGSA-N Salicin Natural products O([C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H](CO)O1)c1c(CO)cccc1 NGFMICBWJRZIBI-JZRPKSSGSA-N 0.000 description 1
241000193996 Streptococcus pyogenes Species 0.000 description 1
229930006000 Sucrose Natural products 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
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 description 1
229930003779 Vitamin B12 Natural products 0.000 description 1
QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 description 1
229930003427 Vitamin E Natural products 0.000 description 1
238000002441 X-ray diffraction Methods 0.000 description 1
PYMYPHUHKUWMLA-VPENINKCSA-N aldehydo-D-xylose Chemical compound OC[C@@H](O)[C@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-VPENINKCSA-N 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 1
NGFMICBWJRZIBI-UHFFFAOYSA-N alpha-salicin Natural products OC1C(O)C(O)C(CO)OC1OC1=CC=CC=C1CO NGFMICBWJRZIBI-UHFFFAOYSA-N 0.000 description 1
150000001449 anionic compounds Chemical class 0.000 description 1
239000002518 antifoaming agent Substances 0.000 description 1
229960004217 benzyl alcohol Drugs 0.000 description 1
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 1
230000002051 biphasic effect Effects 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
229910000389 calcium phosphate Inorganic materials 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
235000014633 carbohydrates Nutrition 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 description 1
229960003178 choline chloride Drugs 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
239000003245 coal Substances 0.000 description 1
AGVAZMGAQJOSFJ-WZHZPDAFSA-M cobalt(2+);[(2r,3s,4r,5s)-5-(5,6-dimethylbenzimidazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] [(2r)-1-[3-[(1r,2r,3r,4z,7s,9z,12s,13s,14z,17s,18s,19r)-2,13,18-tris(2-amino-2-oxoethyl)-7,12,17-tris(3-amino-3-oxopropyl)-3,5,8,8,13,15,18,19-octamethyl-2 Chemical compound [Co+2].N#[C-].[N-]([C@@H]1[C@H](CC(N)=O)[C@@]2(C)CCC(=O)NC[C@@H](C)OP(O)(=O)O[C@H]3[C@H]([C@H](O[C@@H]3CO)N3C4=CC(C)=C(C)C=C4N=C3)O)\C2=C(C)/C([C@H](C\2(C)C)CCC(N)=O)=N/C/2=C\C([C@H]([C@@]/2(CC(N)=O)C)CCC(N)=O)=N\C\2=C(C)/C2=N[C@]1(C)[C@@](C)(CC(N)=O)[C@@H]2CCC(N)=O AGVAZMGAQJOSFJ-WZHZPDAFSA-M 0.000 description 1
239000003086 colorant Substances 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
239000012045 crude solution Substances 0.000 description 1
HEBKCHPVOIAQTA-NGQZWQHPSA-N d-xylitol Chemical compound OC[C@H](O)C(O)[C@H](O)CO HEBKCHPVOIAQTA-NGQZWQHPSA-N 0.000 description 1
230000007423 decrease Effects 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000010828 elution Methods 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
238000011049 filling Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000004467 fishmeal Substances 0.000 description 1
239000004088 foaming agent Substances 0.000 description 1
229960000304 folic acid Drugs 0.000 description 1
235000019152 folic acid Nutrition 0.000 description 1
239000011724 folic acid Substances 0.000 description 1
235000013305 food Nutrition 0.000 description 1
229930182830 galactose Natural products 0.000 description 1
WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
235000021312 gluten Nutrition 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
230000003053 immunization Effects 0.000 description 1
238000002649 immunization Methods 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
229910001412 inorganic anion Inorganic materials 0.000 description 1
229910001411 inorganic cation Inorganic materials 0.000 description 1
238000009413 insulation Methods 0.000 description 1
BJHIKXHVCXFQLS-UYFOZJQFSA-N keto-D-fructose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C(=O)CO BJHIKXHVCXFQLS-UYFOZJQFSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
231100001231 less toxic Toxicity 0.000 description 1
XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
229910052808 lithium carbonate Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
235000012054 meals Nutrition 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
FFEARJCKVFRZRR-UHFFFAOYSA-N methionine Chemical compound CSCCC(N)C(O)=O FFEARJCKVFRZRR-UHFFFAOYSA-N 0.000 description 1
229930182817 methionine Natural products 0.000 description 1
235000006109 methionine Nutrition 0.000 description 1
229940080839 methionine 500 mg Drugs 0.000 description 1
235000013379 molasses Nutrition 0.000 description 1
239000011733 molybdenum Substances 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229960003512 nicotinic acid Drugs 0.000 description 1
235000001968 nicotinic acid Nutrition 0.000 description 1
239000011664 nicotinic acid Substances 0.000 description 1
150000002826 nitrites Chemical class 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
238000010899 nucleation Methods 0.000 description 1
210000003250 oocyst Anatomy 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229940055726 pantothenic acid Drugs 0.000 description 1
235000019161 pantothenic acid Nutrition 0.000 description 1
239000011713 pantothenic acid Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
244000144977 poultry Species 0.000 description 1
235000013594 poultry meat Nutrition 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
239000003531 protein hydrolysate Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000012827 research and development Methods 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
235000019192 riboflavin Nutrition 0.000 description 1
239000002151 riboflavin Substances 0.000 description 1
229960002477 riboflavin Drugs 0.000 description 1
NGFMICBWJRZIBI-UJPOAAIJSA-N salicin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=CC=C1CO NGFMICBWJRZIBI-UJPOAAIJSA-N 0.000 description 1
229940120668 salicin Drugs 0.000 description 1
238000005070 sampling Methods 0.000 description 1
239000004576 sand Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
241000894007 species Species 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
239000000725 suspension Substances 0.000 description 1
235000015113 tomato pastes and purées Nutrition 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
229960005486 vaccine Drugs 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
235000019155 vitamin A Nutrition 0.000 description 1
239000011719 vitamin A Substances 0.000 description 1
235000019163 vitamin B12 Nutrition 0.000 description 1
239000011715 vitamin B12 Substances 0.000 description 1
QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 description 1
235000005282 vitamin D3 Nutrition 0.000 description 1
239000011647 vitamin D3 Substances 0.000 description 1
235000019165 vitamin E Nutrition 0.000 description 1
229940046009 vitamin E Drugs 0.000 description 1
239000011709 vitamin E Substances 0.000 description 1
235000012711 vitamin K3 Nutrition 0.000 description 1
239000011652 vitamin K3 Substances 0.000 description 1
229940045997 vitamin a Drugs 0.000 description 1
229940021056 vitamin d3 Drugs 0.000 description 1
229940041603 vitamin k 3 Drugs 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Health & Medical Sciences (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Life Sciences & Earth Sciences (AREA)
Micro-Organisms Or Cultivation Processes Thereof (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)

CS425777A 1976-06-30 1977-06-28 method of making the antibiotics CS207462B1 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US70139576A	1976-06-30	1976-06-30

Publications (1)

Publication Number	Publication Date
CS207462B1 true CS207462B1 (en)	1981-07-31

Family

ID=24817205

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS425777A CS207462B1 (en)	1976-06-30	1977-06-28	method of making the antibiotics

Country Status (5)

Country	Link
US (1)	US4138481A (fr)
BE (1)	BE856314A (fr)
CS (1)	CS207462B1 (fr)
SU (1)	SU715034A3 (fr)
ZA (1)	ZA773288B (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4232006A (en) *	1977-02-09	1980-11-04	Schering Corporation	Antibiotic W-10 complex, antibiotic 20561 and antibiotic 20562 as antifungal agents
US4263427A (en) *	1978-11-29	1981-04-21	Hoffmann-La Roche Inc.	Monensin urethane derivatives
JPS5592387A (en) *	1978-12-29	1980-07-12	Taisho Pharmaceut Co Ltd	Antibiotic substance tm-531
US4294925A (en) *	1979-09-20	1981-10-13	Hoffmann-La Roche Inc.	Monensin urethane derivatives produced by streptomyces
US4278663A (en) *	1980-01-30	1981-07-14	Hoffmann-La Roche Inc.	Antibiotic X-14868A, B, C and D
JPS577492A (en)	1980-06-13	1982-01-14	Shionogi & Co Ltd	K-41 derivative
JPS5758687A (en) *	1980-09-27	1982-04-08	Taisho Pharmaceut Co Ltd	Antibiotic
US5043353A (en) *	1989-10-10	1991-08-27	Eli Lilly And Company	A80789 polyether antibiotic
US5242814A (en) *	1989-10-10	1993-09-07	Eli Lilly And Company	Polyether antibiotic

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3595955A (en) *	1969-03-26	1971-07-27	Upjohn Co	Geldanamycin and process for producing same
US3812249A (en) *	1972-11-24	1974-05-21	American Cyanamid Co	Antibiotic bl580
US4024251A (en) *	1974-08-13	1977-05-17	Merck & Co., Inc.	Antibiotic FR-02A and therapeutic compositions thereof

1977
- 1977-01-04 US US05/756,659 patent/US4138481A/en not_active Expired - Lifetime
- 1977-06-01 ZA ZA00773288A patent/ZA773288B/xx unknown
- 1977-06-28 CS CS425777A patent/CS207462B1/cs unknown
- 1977-06-29 SU SU772497857A patent/SU715034A3/ru active
- 1977-06-30 BE BE178951A patent/BE856314A/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
ZA773288B (en)	1978-04-26
BE856314A (fr)	1977-12-30
US4138481A (en)	1979-02-06
SU715034A3 (ru)	1980-02-05

Publication	Publication Date	Title
EP0063456B1 (fr)	1984-08-01	Pseudoaminosucres, leur préparation et utilisation
KR900006233B1 (ko)	1990-08-27	폴리사이클릭 에테르 항생물질의 제조방법
CS207462B1 (en)	1981-07-31	method of making the antibiotics
US4539203A (en)	1985-09-03	CL-1577D And CL-1577E antibiotic/antitumor compounds, their production and use
US4661353A (en)	1987-04-28	CL-1577-B4 compound, its production and use
CA1225333A (fr)	1987-08-11	Agents antiviraux
US3812249A (en)	1974-05-21	Antibiotic bl580
CA1337337C (fr)	1995-10-17	Antibiotique de type ether polycyclique acide presentant une activite de coccidiostat et d'anabolisant
CS229936B2 (en)	1984-07-16	Production method of polycyclic ehter type new acid antibiotic
US4189537A (en)	1980-02-19	Process of producing antibiotic BL580Δ with Streptomyces hygroscopicus
KR870001147B1 (ko)	1987-06-11	19-에피-디아네마이신의 제조방법
US4132779A (en)	1979-01-02	Antibiotic BL580 Zeta and use thereof as anticoccidial agent
US5064855A (en)	1991-11-12	Acid polycyclic ether antibiotic
CA1093999A (fr)	1981-01-20	Bl580.delta., antibiotique produit par le streptomices hygroscopicus
US4615975A (en)	1986-10-07	Purified culture of Actinomadura verrucaspora subspecies veractimyces
US5427941A (en)	1995-06-27	Actinomadura brunnea var. antibiotica strains
US4920050A (en)	1990-04-24	Acidic polycyclic ether antibiotic
KR810001709B1 (ko)	1981-10-27	항생제 bl580△의 제조방법
US5403738A (en)	1995-04-04	Microorganism for producing polycyclic ether antibiotics
US3907643A (en)	1975-09-23	Process for producing the antibiotic U-44,590
US3734832A (en)	1973-05-22	Fermentation process for producing physostigmine
EP0553106B1 (fr)	1997-01-22	Antibiotique anticoccidien et stimulateur de croissance du groupe ether polycyclique d'antibiotiques
US5183758A (en)	1993-02-02	Production of 7-chloro-3-methoxy-2'-N-methyltetracycline with Actinomadura brunnea
IE54813B1 (en)	1990-02-14	Microorganism actinomadura yumaense sp.nov. and use thereof to prepare antibiotics ll-c23024 alpha, beta and iota
WO1989012105A1 (fr)	1989-12-14	Antibiotique a base d'ether polycyclique acide ayant une activite anticoccidie et stimulant la croissance