CA1171869A - Tylactone - Google Patents

Tylactone

Info

Publication number: CA1171869A
Authority: CA; Canada
Prior art keywords: tylactone; tylosin; medium; prepared; compound
Prior art date: 1980-07-02
Legal status (The legal status 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 status listed.): Expired

Application number

CA000380953A

Other languages

English (en)

Inventor

Robert L. Hamill

Richard H. Baltz

Gerald L. Huff

Eugene T. Seno

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Eli Lilly and Co

Original Assignee

Eli Lilly and 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.)

1980-07-02

Filing date

1981-06-30

Publication date

1984-07-31

1981-06-30 Application filed by Eli Lilly and Co filed Critical Eli Lilly and Co

1984-07-31 Application granted granted Critical

1984-07-31 Publication of CA1171869A publication Critical patent/CA1171869A/fr

Status Expired legal-status Critical Current

Links

YJSXTLYNFBFHAT-UHFFFAOYSA-N Protylonolide Natural products CCC1CC(C)C(=O)C=CC(C)=CC(C)C(CC)OC(=O)CC(O)C(C)C1O YJSXTLYNFBFHAT-UHFFFAOYSA-N 0.000 title claims abstract description 57
YJSXTLYNFBFHAT-HJOMEYPASA-N tylactone Chemical compound CC[C@H]1C[C@@H](C)C(=O)\C=C\C(\C)=C\[C@H](C)[C@@H](CC)OC(=O)C[C@@H](O)[C@H](C)[C@H]1O YJSXTLYNFBFHAT-HJOMEYPASA-N 0.000 title claims abstract description 57
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
238000000034 method Methods 0.000 claims description 32
150000001875 compounds Chemical class 0.000 claims description 15
230000008569 process Effects 0.000 claims description 13
-1 acyl ester derivative of tylactone Chemical class 0.000 claims description 10
239000003795 chemical substances by application Substances 0.000 claims description 10
150000002148 esters Chemical class 0.000 claims description 10
238000004519 manufacturing process Methods 0.000 claims description 10
239000000126 substance Substances 0.000 claims description 9
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical group CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 6
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical group CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 claims description 2
150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims description 2
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical group CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 claims description 2
NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical group CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 claims 1
FREZLSIGWNCSOQ-UHFFFAOYSA-N 3-methylbutanoyl 3-methylbutanoate Chemical group CC(C)CC(=O)OC(=O)CC(C)C FREZLSIGWNCSOQ-UHFFFAOYSA-N 0.000 claims 1
239000003120 macrolide antibiotic agent Substances 0.000 abstract description 7
125000002252 acyl group Chemical group 0.000 abstract description 4
239000000543 intermediate Substances 0.000 abstract description 4
238000002360 preparation method Methods 0.000 abstract description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 29
WBPYTXDJUQJLPQ-VMXQISHHSA-N tylosin Chemical compound O([C@@H]1[C@@H](C)O[C@H]([C@@H]([C@H]1N(C)C)O)O[C@@H]1[C@@H](C)[C@H](O)CC(=O)O[C@@H]([C@H](/C=C(\C)/C=C/C(=O)[C@H](C)C[C@@H]1CC=O)CO[C@H]1[C@@H]([C@H](OC)[C@H](O)[C@@H](C)O1)OC)CC)[C@H]1C[C@@](C)(O)[C@@H](O)[C@H](C)O1 WBPYTXDJUQJLPQ-VMXQISHHSA-N 0.000 description 26
229930194936 Tylosin Natural products 0.000 description 25
239000004182 Tylosin Substances 0.000 description 25
229960004059 tylosin Drugs 0.000 description 25
235000019375 tylosin Nutrition 0.000 description 25
239000002609 medium Substances 0.000 description 21
238000000855 fermentation Methods 0.000 description 16
230000004151 fermentation Effects 0.000 description 16
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
241000187438 Streptomyces fradiae Species 0.000 description 9
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 8
240000008042 Zea mays Species 0.000 description 8
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 8
235000002017 Zea mays subsp mays Nutrition 0.000 description 8
235000005822 corn Nutrition 0.000 description 8
239000001963 growth medium Substances 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
239000000203 mixture Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
238000001514 detection method Methods 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
229960001866 silicon dioxide Drugs 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
239000002054 inoculum Substances 0.000 description 5
235000012054 meals Nutrition 0.000 description 5
244000005700 microbiome Species 0.000 description 5
239000003921 oil Substances 0.000 description 5
235000019198 oils Nutrition 0.000 description 5
235000012424 soybean oil Nutrition 0.000 description 5
239000003549 soybean oil Substances 0.000 description 5
238000004809 thin layer chromatography Methods 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
235000010216 calcium carbonate Nutrition 0.000 description 4
229910000019 calcium carbonate Inorganic materials 0.000 description 4
238000000605 extraction Methods 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
235000019733 Fish meal Nutrition 0.000 description 3
241000187747 Streptomyces Species 0.000 description 3
238000000862 absorption spectrum Methods 0.000 description 3
239000002253 acid Substances 0.000 description 3
229940072049 amyl acetate Drugs 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
239000004467 fishmeal Substances 0.000 description 3
MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
239000003471 mutagenic agent Substances 0.000 description 3
231100000707 mutagenic chemical Toxicity 0.000 description 3
150000007524 organic acids Chemical class 0.000 description 3
239000013587 production medium Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
235000016068 Berberis vulgaris Nutrition 0.000 description 2
241000335053 Beta vulgaris Species 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 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
108010068370 Glutens Proteins 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
VZUNGTLZRAYYDE-UHFFFAOYSA-N N-methyl-N'-nitro-N-nitrosoguanidine Chemical compound O=NN(C)C(=N)N[N+]([O-])=O VZUNGTLZRAYYDE-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
230000010933 acylation Effects 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
238000010564 aerobic fermentation Methods 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
229940041514 candida albicans extract Drugs 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
238000012258 culturing Methods 0.000 description 2
239000008367 deionised water Substances 0.000 description 2
229910021641 deionized water Inorganic materials 0.000 description 2
230000032050 esterification Effects 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000005755 formation reaction Methods 0.000 description 2
235000001727 glucose Nutrition 0.000 description 2
239000008103 glucose Substances 0.000 description 2
235000021312 gluten Nutrition 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
238000011081 inoculation Methods 0.000 description 2
238000002955 isolation Methods 0.000 description 2
239000000787 lecithin Substances 0.000 description 2
229940067606 lecithin Drugs 0.000 description 2
235000010445 lecithin Nutrition 0.000 description 2
235000013379 molasses Nutrition 0.000 description 2
238000002703 mutagenesis Methods 0.000 description 2
231100000350 mutagenesis Toxicity 0.000 description 2
230000003505 mutagenic effect Effects 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
238000012807 shake-flask culturing Methods 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
239000007921 spray Substances 0.000 description 2
235000000346 sugar Nutrition 0.000 description 2
238000012360 testing method Methods 0.000 description 2
235000013619 trace mineral Nutrition 0.000 description 2
239000011573 trace mineral Substances 0.000 description 2
239000012138 yeast extract Substances 0.000 description 2
SMJRBWINMFUUDS-UHFFFAOYSA-N 2-thienylacetic acid Chemical class OC(=O)CC1=CC=CS1 SMJRBWINMFUUDS-UHFFFAOYSA-N 0.000 description 1
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
229940126062 Compound A Drugs 0.000 description 1
229920001353 Dextrin Polymers 0.000 description 1
239000004375 Dextrin Substances 0.000 description 1
244000068988 Glycine max Species 0.000 description 1
235000010469 Glycine max Nutrition 0.000 description 1
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
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 1
239000005909 Kieselgur Substances 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
241000364057 Peoria Species 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
235000019764 Soybean Meal Nutrition 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
JIMXXGFJRDUSRO-UHFFFAOYSA-N adamantane-1-carboxylic acid Chemical compound C1C(C2)CC3CC2CC1(C(=O)O)C3 JIMXXGFJRDUSRO-UHFFFAOYSA-N 0.000 description 1
235000016127 added sugars Nutrition 0.000 description 1
238000005377 adsorption chromatography Methods 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
235000001014 amino acid Nutrition 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
230000000845 anti-microbial effect Effects 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
239000002518 antifoaming agent Substances 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
238000003556 assay Methods 0.000 description 1
SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
238000004166 bioassay Methods 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
235000014633 carbohydrates Nutrition 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000000470 constituent Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 1
YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
238000011161 development Methods 0.000 description 1
235000019425 dextrin Nutrition 0.000 description 1
229910000388 diammonium phosphate Inorganic materials 0.000 description 1
150000001991 dicarboxylic acids Chemical class 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000010828 elution Methods 0.000 description 1
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000005187 foaming Methods 0.000 description 1
239000012634 fragment Substances 0.000 description 1
150000002238 fumaric acids Chemical class 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000010565 inoculated fermentation Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
238000002372 labelling Methods 0.000 description 1
150000002632 lipids Chemical class 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
150000002689 maleic acids Chemical class 0.000 description 1
150000002691 malonic acids Chemical class 0.000 description 1
239000000155 melt Substances 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
230000037353 metabolic pathway Effects 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
238000010979 pH adjustment Methods 0.000 description 1
239000008188 pellet Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
150000003022 phthalic acids Chemical class 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
239000000047 product Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000002516 radical scavenger Substances 0.000 description 1
238000011160 research Methods 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
238000012216 screening Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000004455 soybean meal Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
150000003444 succinic acids Chemical class 0.000 description 1
238000004448 titration Methods 0.000 description 1

Landscapes

Preparation Of Compounds By Using Micro-Organisms (AREA)

CA000380953A 1980-07-02 1981-06-30 Tylactone Expired CA1171869A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US16297680A	1980-07-02	1980-07-02
US162,976		1980-07-02

Publications (1)

Publication Number	Publication Date
CA1171869A true CA1171869A (fr)	1984-07-31

Family

ID=22587915

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000380953A Expired CA1171869A (fr)	1980-07-02	1981-06-30	Tylactone

Country Status (1)

Country	Link
CA (1)	CA1171869A (fr)

1981
- 1981-06-30 CA CA000380953A patent/CA1171869A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2001-07-31	MKEX	Expiry

Publication	Publication Date	Title
US4151042A (en)	1979-04-24	Method for producing maytansinol and its derivatives
CA1155073A (fr)	1983-10-11	Antibiotique c-15003 et procede de production
EP0042250B1 (fr)	1984-03-07	Antibiotiques macrolidiques
US4299953A (en)	1981-11-10	Mycarosyltylactone
CA1169374A (fr)	1984-06-19	Methode d'obtention de 20-dihydro-20-desoxy-23- demycinosyltylosine et de 20-dihydro-20-desoxy-5-0- mycaminosyltylonolide
EP0043280B1 (fr)	1984-03-14	Procédé pour la préparation d'un macrolide
US4362881A (en)	1982-12-07	Tylactone
US4440857A (en)	1984-04-03	Process for preparing mycarosyltylactone
EP0042694B1 (fr)	1984-03-07	Antibiotiques macrolidiques
EP0045205B1 (fr)	1984-10-03	Macrolides
EP0028511A1 (fr)	1981-05-13	Céphalosporines, procédés pour leur préparation et microorganismes appropriés à leur production
US3988314A (en)	1976-10-26	Compound U-50,228, derivatives thereof, and processes for preparation
EP0045157B1 (fr)	1984-04-18	Antibiotiques macrolides, leur préparation et compositions vétérinaires les contenant
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