CH619267A5 - - Google Patents
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- Publication number
- CH619267A5 CH619267A5 CH946076A CH946076A CH619267A5 CH 619267 A5 CH619267 A5 CH 619267A5 CH 946076 A CH946076 A CH 946076A CH 946076 A CH946076 A CH 946076A CH 619267 A5 CH619267 A5 CH 619267A5
- Authority
- CH
- Switzerland
- Prior art keywords
- acylation
- group
- coa
- substrate
- hydroxyl group
- Prior art date
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- WBPYTXDJUQJLPQ-VMXQISHHSA-N tylosin Chemical class 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 claims description 99
- 239000004182 Tylosin Substances 0.000 claims description 88
- 229960004059 tylosin Drugs 0.000 claims description 88
- 229930194936 Tylosin Natural products 0.000 claims description 81
- 235000019375 tylosin Nutrition 0.000 claims description 81
- 239000000758 substrate Substances 0.000 claims description 80
- 238000000034 method Methods 0.000 claims description 77
- 238000005917 acylation reaction Methods 0.000 claims description 70
- 239000003120 macrolide antibiotic agent Substances 0.000 claims description 66
- ZSLZBFCDCINBPY-ZSJPKINUSA-N acetyl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 ZSLZBFCDCINBPY-ZSJPKINUSA-N 0.000 claims description 64
- 230000010933 acylation Effects 0.000 claims description 63
- 239000000047 product Substances 0.000 claims description 58
- 125000002252 acyl group Chemical group 0.000 claims description 44
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 37
- 239000002243 precursor Substances 0.000 claims description 32
- UYVZIWWBJMYRCD-ZMHDXICWSA-N isovaleryl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CC(C)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 UYVZIWWBJMYRCD-ZMHDXICWSA-N 0.000 claims description 29
- -1 n-butyryl CoA Chemical compound 0.000 claims description 28
- 230000008569 process Effects 0.000 claims description 28
- QAQREVBBADEHPA-IEXPHMLFSA-N propionyl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CC)O[C@H]1N1C2=NC=NC(N)=C2N=C1 QAQREVBBADEHPA-IEXPHMLFSA-N 0.000 claims description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- 239000004187 Spiramycin Substances 0.000 claims description 23
- 229930191512 spiramycin Natural products 0.000 claims description 23
- 235000019372 spiramycin Nutrition 0.000 claims description 23
- 229960001294 spiramycin Drugs 0.000 claims description 21
- 230000003115 biocidal effect Effects 0.000 claims description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 244000005700 microbiome Species 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 16
- 241000187747 Streptomyces Species 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 13
- 230000012010 growth Effects 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- 238000006640 acetylation reaction Methods 0.000 claims description 11
- 230000002255 enzymatic effect Effects 0.000 claims description 11
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 11
- 241001465754 Metazoa Species 0.000 claims description 10
- 230000021736 acetylation Effects 0.000 claims description 10
- 239000007853 buffer solution Substances 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 230000006289 propionylation Effects 0.000 claims description 8
- 238000010515 propionylation reaction Methods 0.000 claims description 8
- 239000000654 additive Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 241001600136 Streptomyces thermotolerans Species 0.000 claims description 6
- 238000010514 butyrylation reaction Methods 0.000 claims description 6
- 239000000725 suspension Substances 0.000 claims description 5
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- 241000187391 Streptomyces hygroscopicus Species 0.000 claims description 3
- 241000187233 Streptomyces mycarofaciens Species 0.000 claims description 3
- 230000001737 promoting effect Effects 0.000 claims description 3
- 230000000996 additive effect Effects 0.000 claims description 2
- 239000000706 filtrate Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- ACTOXUHEUCPTEW-BWHGAVFKSA-N 2-[(4r,5s,6s,7r,9r,10r,11e,13e,16r)-6-[(2s,3r,4r,5s,6r)-5-[(2s,4r,5s,6s)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-10-[(2s,5s,6r)-5-(dimethylamino)-6-methyloxan-2-yl]oxy-4-hydroxy-5-methoxy-9,16-dimethyl-2-o Chemical compound O([C@H]1/C=C/C=C/C[C@@H](C)OC(=O)C[C@@H](O)[C@@H]([C@H]([C@@H](CC=O)C[C@H]1C)O[C@H]1[C@@H]([C@H]([C@H](O[C@@H]2O[C@@H](C)[C@H](O)[C@](C)(O)C2)[C@@H](C)O1)N(C)C)O)OC)[C@@H]1CC[C@H](N(C)C)[C@@H](C)O1 ACTOXUHEUCPTEW-BWHGAVFKSA-N 0.000 claims 1
- 241000971005 Streptomyces fungicidicus Species 0.000 claims 1
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- RGJOEKWQDUBAIZ-UHFFFAOYSA-N coenzime A Natural products OC1C(OP(O)(O)=O)C(COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)OC1N1C2=NC=NC(N)=C2N=C1 RGJOEKWQDUBAIZ-UHFFFAOYSA-N 0.000 description 1
- 239000005516 coenzyme A Substances 0.000 description 1
- 229940093530 coenzyme a Drugs 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000013409 condiments Nutrition 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000012136 culture method Methods 0.000 description 1
- 230000020176 deacylation Effects 0.000 description 1
- 238000005947 deacylation reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- KDTSHFARGAKYJN-UHFFFAOYSA-N dephosphocoenzyme A Natural products OC1C(O)C(COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)OC1N1C2=NC=NC(N)=C2N=C1 KDTSHFARGAKYJN-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- HBFXVTVOSLPOEY-UHFFFAOYSA-N ethoxyethane;2-propan-2-yloxypropane Chemical compound CCOCC.CC(C)OC(C)C HBFXVTVOSLPOEY-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 238000013467 fragmentation Methods 0.000 description 1
- 238000006062 fragmentation reaction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000007986 glycine-NaOH buffer Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- JYVHOGDBFNJNMR-UHFFFAOYSA-N hexane;hydrate Chemical compound O.CCCCCC JYVHOGDBFNJNMR-UHFFFAOYSA-N 0.000 description 1
- 229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
- 229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 235000020429 malt syrup Nutrition 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
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 229960002351 oleandomycin Drugs 0.000 description 1
- RZPAKFUAFGMUPI-KGIGTXTPSA-N oleandomycin Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](C)C(=O)O[C@H](C)[C@H](C)[C@H](O)[C@@H](C)C(=O)[C@]2(OC2)C[C@H](C)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C RZPAKFUAFGMUPI-KGIGTXTPSA-N 0.000 description 1
- 235000019367 oleandomycin Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- YLLIGHVCTUPGEH-UHFFFAOYSA-M potassium;ethanol;hydroxide Chemical compound [OH-].[K+].CCO YLLIGHVCTUPGEH-UHFFFAOYSA-M 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000010414 supernatant solution Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000080 wetting agent Substances 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
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/44—Preparation of O-glycosides, e.g. glucosides
- C12P19/60—Preparation of O-glycosides, e.g. glucosides having an oxygen of the saccharide radical directly bound to a non-saccharide heterocyclic ring or a condensed ring system containing a non-saccharide heterocyclic ring, e.g. coumermycin, novobiocin
- C12P19/62—Preparation of O-glycosides, e.g. glucosides having an oxygen of the saccharide radical directly bound to a non-saccharide heterocyclic ring or a condensed ring system containing a non-saccharide heterocyclic ring, e.g. coumermycin, novobiocin the hetero ring having eight or more ring members and only oxygen as ring hetero atoms, e.g. erythromycin, spiramycin, nystatin
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/886—Streptomyces
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9305375A JPS5218889A (en) | 1975-08-01 | 1975-08-01 | Biochemical acetylation of macrolide antibiotics |
| JP50110010A JPS5234983A (en) | 1975-09-12 | 1975-09-12 | Biochemical acylation of macrolide antibiotics |
| JP15838875A JPS5282790A (en) | 1975-12-27 | 1975-12-27 | Preparation of macroride antibiotics |
| JP5562676A JPS52139088A (en) | 1976-05-15 | 1976-05-15 | Antibiotics tyrocin derivatives and their preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH619267A5 true CH619267A5 (ko) | 1980-09-15 |
Family
ID=27463226
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH946076A CH619267A5 (ko) | 1975-08-01 | 1976-07-23 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4092473A (ko) |
| BR (1) | BR7605024A (ko) |
| CA (1) | CA1063954A (ko) |
| CH (1) | CH619267A5 (ko) |
| DE (1) | DE2634499C2 (ko) |
| DK (1) | DK151262C (ko) |
| ES (1) | ES450333A1 (ko) |
| FR (1) | FR2319374A1 (ko) |
| GB (1) | GB1539907A (ko) |
| NL (1) | NL176087C (ko) |
| SE (1) | SE441598B (ko) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4205163A (en) * | 1977-11-08 | 1980-05-27 | Sanraku-Ocean Co., Ltd. | Tylosin derivatives |
| SE445739B (sv) * | 1978-09-14 | 1986-07-14 | Toyo Jozo Kk | 3", 4"-diacyltylosinderivat |
| US4349665A (en) * | 1980-06-27 | 1982-09-14 | Schering Corporation | Macrolide antibiotic complex |
| US4362881A (en) * | 1980-07-02 | 1982-12-07 | Eli Lilly And Company | Tylactone |
| US4299953A (en) * | 1980-07-29 | 1981-11-10 | Eli Lilly And Company | Mycarosyltylactone |
| US4357325A (en) * | 1981-04-20 | 1982-11-02 | Eli Lilly And Company | Methods of controlling Pasteurella infections |
| US4401660A (en) * | 1981-12-14 | 1983-08-30 | Eli Lilly And Company | Ester derivatives of 5-O-mycaminosyl tylonolide and method of using same |
| US4396613A (en) * | 1981-12-14 | 1983-08-02 | Eli Lilly And Company | 23-Ester derivatives of DMT and method of using same |
| US4487923A (en) * | 1981-12-14 | 1984-12-11 | Eli Lilly And Company | Method of preparing 23-monoesters of OMT and DMT |
| US4436733A (en) | 1982-03-03 | 1984-03-13 | Eli Lilly And Company | 4"- And 3-ester derivatives of DMT and DMOT |
| US4597969A (en) * | 1982-04-05 | 1986-07-01 | Merck Sharp & Dohme | Stabilization of unstable drugs or food supplements |
| US4412359A (en) * | 1982-04-26 | 1983-11-01 | Myers William D | Posterior chamber lens implant |
| DK144084A (da) * | 1983-03-03 | 1984-09-04 | Lilly Co Eli | Makrolid, dets fremstilling og anvendelse |
| US4559301A (en) * | 1983-03-03 | 1985-12-17 | Eli Lilly And Company | Process for preparing macrocin derivatives |
| US4656258A (en) * | 1983-03-03 | 1987-04-07 | Eli Lilly And Company | Macrocin derivatives |
| US4594337A (en) * | 1983-03-03 | 1986-06-10 | Eli Lilly And Company | Methods of controlling mycoplasma infections |
| US4522919A (en) * | 1983-03-03 | 1985-06-11 | Eli Lilly And Company | Method of producing antibacterial agents and bioconverting microorganism therefor |
| JP3074039B2 (ja) * | 1991-08-07 | 2000-08-07 | 明治製菓株式会社 | １６員環マクロライド抗生物質の３位脱アシル体の製造法及びこれに用いる微生物並びに新規マクロライド抗生物質 |
| GB0025556D0 (en) * | 2000-10-18 | 2000-12-06 | Eco Animal Health Ltd | Treatment and prophylaxis of disease and infections of pigs and poultry |
| GB0315629D0 (en) * | 2003-07-03 | 2003-08-13 | Eco Animal Health Ltd | New uses for antibiotic |
| ATE468119T1 (de) | 2006-06-12 | 2010-06-15 | Univ Ramot | Verfahren zur behandlung von krebs |
| PT2043661E (pt) | 2006-07-13 | 2014-12-22 | Eco Animal Health Ltd | Uso de tilvalosina como agente antiviral |
| CN102659882B (zh) * | 2012-05-11 | 2015-04-22 | 湖北泱盛生物科技有限公司 | 一种酒石酸乙酰异戊酰泰乐菌素的提取方法 |
| CN104693255B (zh) * | 2015-01-14 | 2017-05-24 | 宁夏泰瑞制药股份有限公司 | 从酒石酸乙酰异戊酰泰乐菌素结晶母液中回收酒石酸乙酰异戊酰泰乐碱的方法 |
| CN104961784A (zh) * | 2015-06-11 | 2015-10-07 | 宁夏泰瑞制药股份有限公司 | 一种从酒石酸乙酰异戊酰泰乐菌素结晶母液中回收乙酰异戊酰泰乐碱的方法 |
| CN108358979B (zh) * | 2018-05-22 | 2020-08-25 | 中牧实业股份有限公司 | 泰万菌素的纯化方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1278441B (de) * | 1958-10-29 | 1968-09-26 | Lilly Co Eli | Verfahren zur Herstellung von Acylderivaten von Tylosin und Desmycosin und deren Salzen |
| NO116467B (ko) * | 1965-03-02 | 1969-03-31 | Rhone Poulenc Sa | |
| FI56187C (fi) * | 1970-07-02 | 1979-12-10 | Takeda Chemical Industries Ltd | Foerfarande foer framstaellning av antibiotiskt aktiva estrar av makrolidglykosiderna b-5050 eller tetrahydro b-5050 |
-
1976
- 1976-07-23 US US05/708,151 patent/US4092473A/en not_active Expired - Lifetime
- 1976-07-23 CH CH946076A patent/CH619267A5/fr not_active IP Right Cessation
- 1976-07-26 SE SE7608448A patent/SE441598B/xx not_active IP Right Cessation
- 1976-07-26 GB GB31117/76A patent/GB1539907A/en not_active Expired
- 1976-07-29 NL NLAANVRAGE7608411,A patent/NL176087C/xx not_active IP Right Cessation
- 1976-07-29 FR FR7623268A patent/FR2319374A1/fr active Granted
- 1976-07-30 CA CA258,132A patent/CA1063954A/en not_active Expired
- 1976-07-30 DK DK344976A patent/DK151262C/da not_active IP Right Cessation
- 1976-07-30 BR BR7605024A patent/BR7605024A/pt unknown
- 1976-07-30 ES ES450333A patent/ES450333A1/es not_active Expired
- 1976-07-31 DE DE2634499A patent/DE2634499C2/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DK151262B (da) | 1987-11-16 |
| FR2319374B1 (ko) | 1978-11-17 |
| ES450333A1 (es) | 1977-11-16 |
| SE441598B (sv) | 1985-10-21 |
| DE2634499A1 (de) | 1977-03-10 |
| DK344976A (da) | 1977-02-02 |
| FR2319374A1 (fr) | 1977-02-25 |
| DK151262C (da) | 1988-05-02 |
| CA1063954A (en) | 1979-10-09 |
| NL176087C (nl) | 1985-02-18 |
| US4092473A (en) | 1978-05-30 |
| GB1539907A (en) | 1979-02-07 |
| NL7608411A (nl) | 1977-02-03 |
| SE7608448L (sv) | 1977-02-02 |
| DE2634499C2 (de) | 1982-05-19 |
| BR7605024A (pt) | 1977-08-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PFA | Name/firm changed |
Owner name: SANRAKU INCORPORATED |
|
| PFA | Name/firm changed |
Owner name: MERCIAN CORPORATION |
|
| PL | Patent ceased |