JP2002535996A - シュードモナス酸群を含む培養液からのシュードモナス酸ａの単離方法 - Google Patents
シュードモナス酸群を含む培養液からのシュードモナス酸ａの単離方法Info
- Publication number
- JP2002535996A JP2002535996A JP2000597447A JP2000597447A JP2002535996A JP 2002535996 A JP2002535996 A JP 2002535996A JP 2000597447 A JP2000597447 A JP 2000597447A JP 2000597447 A JP2000597447 A JP 2000597447A JP 2002535996 A JP2002535996 A JP 2002535996A
- Authority
- JP
- Japan
- Prior art keywords
- pseudomonas
- extract
- acid
- pseudomonas acid
- isobutyl acetate
- Prior art date
- 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.)
- Pending
Links
- 241000589516 Pseudomonas Species 0.000 title claims abstract description 77
- 239000002253 acid Substances 0.000 title claims abstract description 76
- 238000000034 method Methods 0.000 title claims abstract description 42
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 60
- 239000000284 extract Substances 0.000 claims abstract description 49
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Chemical class CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 claims abstract description 45
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical class CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 claims abstract description 45
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Chemical class COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 claims abstract description 45
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000000203 mixture Substances 0.000 claims abstract description 15
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims abstract description 12
- 239000003208 petroleum Substances 0.000 claims abstract description 10
- 230000002378 acidificating effect Effects 0.000 claims abstract description 7
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000000908 ammonium hydroxide Substances 0.000 claims abstract description 6
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 claims abstract description 5
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 5
- 235000012538 ammonium bicarbonate Nutrition 0.000 claims abstract description 5
- 239000001099 ammonium carbonate Substances 0.000 claims abstract description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 5
- 238000000638 solvent extraction Methods 0.000 claims abstract description 5
- 241000894007 species Species 0.000 claims abstract description 3
- 239000000243 solution Substances 0.000 claims description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- 239000010410 layer Substances 0.000 claims description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 11
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 10
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 10
- 238000001704 evaporation Methods 0.000 claims description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 239000003929 acidic solution Substances 0.000 claims description 6
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 238000000746 purification Methods 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 239000012670 alkaline solution Substances 0.000 claims description 4
- 239000012044 organic layer Substances 0.000 claims description 4
- 241000894006 Bacteria Species 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 238000000605 extraction Methods 0.000 abstract description 16
- 230000003115 biocidal effect Effects 0.000 abstract description 13
- 230000020477 pH reduction Effects 0.000 abstract description 4
- 239000006286 aqueous extract Substances 0.000 abstract description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- MINDHVHHQZYEEK-UHFFFAOYSA-N (E)-(2S,3R,4R,5S)-5-[(2S,3S,4S,5S)-2,3-epoxy-5-hydroxy-4-methylhexyl]tetrahydro-3,4-dihydroxy-(beta)-methyl-2H-pyran-2-crotonic acid ester with 9-hydroxynonanoic acid Natural products CC(O)C(C)C1OC1CC1C(O)C(O)C(CC(C)=CC(=O)OCCCCCCCCC(O)=O)OC1 MINDHVHHQZYEEK-UHFFFAOYSA-N 0.000 description 16
- 229960003128 mupirocin Drugs 0.000 description 16
- 229930187697 mupirocin Natural products 0.000 description 16
- DDHVILIIHBIMQU-YJGQQKNPSA-L mupirocin calcium hydrate Chemical compound O.O.[Ca+2].C[C@H](O)[C@H](C)[C@@H]1O[C@H]1C[C@@H]1[C@@H](O)[C@@H](O)[C@H](C\C(C)=C\C(=O)OCCCCCCCCC([O-])=O)OC1.C[C@H](O)[C@H](C)[C@@H]1O[C@H]1C[C@@H]1[C@@H](O)[C@@H](O)[C@H](C\C(C)=C\C(=O)OCCCCCCCCC([O-])=O)OC1 DDHVILIIHBIMQU-YJGQQKNPSA-L 0.000 description 16
- 239000008367 deionised water Substances 0.000 description 14
- 229910021641 deionized water Inorganic materials 0.000 description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- 239000012043 crude product Substances 0.000 description 10
- 238000002425 crystallisation Methods 0.000 description 9
- 230000008025 crystallization Effects 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 150000007513 acids Chemical class 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- 238000005119 centrifugation Methods 0.000 description 7
- 239000012535 impurity Substances 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 239000003242 anti bacterial agent Substances 0.000 description 6
- 239000006228 supernatant Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 230000000813 microbial effect Effects 0.000 description 5
- 229940088710 antibiotic agent Drugs 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 229910003002 lithium salt Inorganic materials 0.000 description 4
- 159000000002 lithium salts Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 239000013543 active substance Substances 0.000 description 3
- -1 bicyclic compound Chemical class 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 238000005352 clarification Methods 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 235000006408 oxalic acid Nutrition 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 241000588747 Klebsiella pneumoniae Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 241000193996 Streptococcus pyogenes Species 0.000 description 2
- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000000855 fermentation Methods 0.000 description 2
- 230000004151 fermentation Effects 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 238000005192 partition Methods 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- MSKQZGZMIMXZEQ-UHFFFAOYSA-N 2-ethylhexanoic acid;lithium Chemical compound [Li].CCCCC(CC)C(O)=O MSKQZGZMIMXZEQ-UHFFFAOYSA-N 0.000 description 1
- 208000002874 Acne Vulgaris Diseases 0.000 description 1
- 238000010953 Ames test Methods 0.000 description 1
- 231100000039 Ames test Toxicity 0.000 description 1
- 102000052866 Amino Acyl-tRNA Synthetases Human genes 0.000 description 1
- 108700028939 Amino Acyl-tRNA Synthetases Proteins 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- OIRAEJWYWSAQNG-UHFFFAOYSA-N Clidanac Chemical compound ClC=1C=C2C(C(=O)O)CCC2=CC=1C1CCCCC1 OIRAEJWYWSAQNG-UHFFFAOYSA-N 0.000 description 1
- 208000003322 Coinfection Diseases 0.000 description 1
- 206010011409 Cross infection Diseases 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- 241000606768 Haemophilus influenzae Species 0.000 description 1
- 206010021531 Impetigo Diseases 0.000 description 1
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 description 1
- 241001601804 Margites Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000588653 Neisseria Species 0.000 description 1
- 241000589540 Pseudomonas fluorescens Species 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 208000006311 Pyoderma Diseases 0.000 description 1
- 229920005654 Sephadex Polymers 0.000 description 1
- 239000012507 Sephadex™ Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 241000193998 Streptococcus pneumoniae Species 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 125000000218 acetic acid group Chemical class C(C)(=O)* 0.000 description 1
- 206010000496 acne Diseases 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000005349 anion exchange Methods 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 159000000009 barium salts Chemical class 0.000 description 1
- 230000003570 biosynthesizing effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 238000011210 chromatographic step Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000002774 effect on peptide Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000009422 growth inhibiting effect Effects 0.000 description 1
- 229940047650 haemophilus influenzae Drugs 0.000 description 1
- MPKNPWYCNYLGSC-UHFFFAOYSA-N heptane;4-methylpentan-2-one Chemical compound CCCCCCC.CC(C)CC(C)=O MPKNPWYCNYLGSC-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229960000310 isoleucine Drugs 0.000 description 1
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- FBUKVWPVBMHYJY-UHFFFAOYSA-N noncarboxylic acid Natural products CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 206010033072 otitis externa Diseases 0.000 description 1
- 150000002913 oxalic acids Chemical class 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 229930194369 pseudomonic acid Natural products 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 206010040872 skin infection Diseases 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229940031000 streptococcus pneumoniae Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000036269 ulceration Effects 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
Classifications
-
- 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
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/02—Oxygen as only ring hetero atoms
-
- 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
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/16—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms containing two or more hetero rings
- C12P17/162—Heterorings having oxygen atoms as the only ring heteroatoms, e.g. Lasalocid
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- General Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Microbiology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11844799P | 1999-02-03 | 1999-02-03 | |
| US60/118,447 | 1999-02-03 | ||
| PCT/US2000/002824 WO2000046388A1 (en) | 1999-02-03 | 2000-02-03 | Process for the isolation of pseudomonic acid a from pseudomonic acid complex-containing culture broth |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002535996A true JP2002535996A (ja) | 2002-10-29 |
| JP2002535996A5 JP2002535996A5 (https=) | 2005-12-22 |
Family
ID=22378653
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000597447A Pending JP2002535996A (ja) | 1999-02-03 | 2000-02-03 | シュードモナス酸群を含む培養液からのシュードモナス酸ａの単離方法 |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US6245921B1 (https=) |
| EP (1) | EP1147210A4 (https=) |
| JP (1) | JP2002535996A (https=) |
| KR (1) | KR20010112258A (https=) |
| CN (1) | CN1345377A (https=) |
| AU (1) | AU771214B2 (https=) |
| BG (1) | BG105775A (https=) |
| BR (1) | BR0009178A (https=) |
| CA (1) | CA2360840A1 (https=) |
| CZ (1) | CZ20012725A3 (https=) |
| HK (1) | HK1041294A1 (https=) |
| HR (1) | HRP20010570A2 (https=) |
| HU (1) | HUP0105286A3 (https=) |
| IL (1) | IL144678A0 (https=) |
| IS (1) | IS6034A (https=) |
| MX (1) | MXPA01007805A (https=) |
| NO (1) | NO20013790L (https=) |
| PL (1) | PL349153A1 (https=) |
| SK (1) | SK10902001A3 (https=) |
| TR (1) | TR200102232T2 (https=) |
| WO (1) | WO2000046388A1 (https=) |
| YU (1) | YU55501A (https=) |
| ZA (1) | ZA200106057B (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008530168A (ja) * | 2005-02-21 | 2008-08-07 | アルファーマ エーピーエス | ムピロシン精製法 |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2360865A1 (en) | 1999-02-03 | 2000-08-10 | Biogal Gyogyszergyar Rt. | Process for the preparation of pseudomonic acid a antibiotic by microbiological method |
| CZ200467A3 (cs) * | 2001-06-21 | 2004-10-13 | Biogalágyogyszergyarárt | Metabolicky řízený způsob fermentace pro výrobu pseudomonové kyseliny |
| PL371263A1 (en) | 2001-12-28 | 2005-06-13 | Biogal Gyogyszergyar Rt | Processes for preparing crystalline and amorphous mupirocin calcium |
| IL150907A (en) * | 2002-07-25 | 2007-07-04 | Stephan Cherkez | Process for the preparation of stable amorphous calcium pseudomonate |
| CA2560984A1 (en) * | 2004-06-01 | 2005-12-15 | Teva Gyogyszergyar Zartkoruen Mukodo Reszvenytarsasag | Process for preparation of amorphous form of a drug |
| GB2441328A (en) * | 2006-08-30 | 2008-03-05 | Alpharma Aps | A method for obtaining mupirocin calcium |
| US8268975B2 (en) | 2009-04-03 | 2012-09-18 | Dow Agrosciences Llc | Demulsification compositions, systems and methods for demulsifying and separating aqueous emulsions |
| CN104370896A (zh) * | 2013-11-29 | 2015-02-25 | 江苏汉邦科技有限公司 | 一种纯化假单孢菌素的方法 |
| CN103820369B (zh) * | 2014-03-07 | 2015-11-18 | 浙江瑞邦药业有限公司 | 一种萤光假单胞菌及其应用 |
| CN109053707B (zh) * | 2018-09-19 | 2021-08-17 | 福建康鸿生物科技有限公司 | 一种莫匹罗星的提纯方法 |
| CN110823649A (zh) * | 2019-10-21 | 2020-02-21 | 河南中烟工业有限责任公司 | 一种卷烟主流烟气中有机酸的收集方法和检测方法 |
| EP4190780A4 (en) * | 2020-08-25 | 2024-03-20 | Hangzhou Zhongmeihuadong Pharmaceutical Co., Ltd. | MUPIROCIN EXTRACTION PROCESS |
| US20240043888A1 (en) * | 2021-02-07 | 2024-02-08 | Hangzhou Zhongmeihuadong Pharmaceutical Co., Ltd. | Fermentation method for mupirocin |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1395907A (en) | 1971-06-12 | 1975-05-29 | Beecham Group Ltd | Antibiotics |
| JPS5270083A (en) | 1975-12-04 | 1977-06-10 | Yoshitomi Pharmaceut Ind Ltd | Manufacture of an antibiotics, trans-pseudomonic acid |
| CA1103264A (en) * | 1977-09-30 | 1981-06-16 | Norman H. Rogers | Purification of pseudomonic acid |
| CA1115699A (en) | 1978-05-20 | 1982-01-05 | Alan D. Curzons | Lithium pseudomonate and its preparation |
| ZA923242B (en) * | 1991-05-07 | 1993-01-27 | Sankyo Co | Novel anti-bacterial compound |
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2000
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- 2000-02-03 PL PL00349153A patent/PL349153A1/xx not_active Application Discontinuation
- 2000-02-03 SK SK1090-2001A patent/SK10902001A3/sk unknown
- 2000-02-03 US US09/497,806 patent/US6245921B1/en not_active Expired - Fee Related
- 2000-02-03 HK HK02103004.6A patent/HK1041294A1/zh unknown
- 2000-02-03 TR TR2001/02232T patent/TR200102232T2/xx unknown
- 2000-02-03 MX MXPA01007805A patent/MXPA01007805A/es unknown
- 2000-02-03 YU YU55501A patent/YU55501A/sh unknown
- 2000-02-03 WO PCT/US2000/002824 patent/WO2000046388A1/en not_active Ceased
- 2000-02-03 KR KR1020017009823A patent/KR20010112258A/ko not_active Ceased
- 2000-02-03 AU AU29802/00A patent/AU771214B2/en not_active Ceased
- 2000-02-03 CZ CZ20012725A patent/CZ20012725A3/cs unknown
- 2000-02-03 EP EP00908467A patent/EP1147210A4/en not_active Withdrawn
- 2000-02-03 HR HR20010570A patent/HRP20010570A2/hr not_active Application Discontinuation
- 2000-02-03 HU HU0105286A patent/HUP0105286A3/hu unknown
- 2000-02-03 BR BR0009178-2A patent/BR0009178A/pt not_active IP Right Cessation
- 2000-02-03 CA CA002360840A patent/CA2360840A1/en not_active Abandoned
- 2000-02-03 CN CN00805537A patent/CN1345377A/zh active Pending
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2001
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- 2001-08-02 NO NO20013790A patent/NO20013790L/no not_active Application Discontinuation
- 2001-08-03 BG BG105775A patent/BG105775A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008530168A (ja) * | 2005-02-21 | 2008-08-07 | アルファーマ エーピーエス | ムピロシン精製法 |
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|---|---|
| AU771214B2 (en) | 2004-03-18 |
| HUP0105286A3 (en) | 2003-03-28 |
| NO20013790L (no) | 2001-10-02 |
| BG105775A (bg) | 2002-03-29 |
| BR0009178A (pt) | 2001-11-20 |
| HRP20010570A2 (en) | 2002-08-31 |
| IL144678A0 (en) | 2002-06-30 |
| CZ20012725A3 (cs) | 2002-03-13 |
| IS6034A (is) | 2001-08-01 |
| HK1041294A1 (zh) | 2002-07-05 |
| YU55501A (sh) | 2003-07-07 |
| AU2980200A (en) | 2000-08-25 |
| KR20010112258A (ko) | 2001-12-20 |
| SK10902001A3 (sk) | 2002-04-04 |
| HUP0105286A2 (hu) | 2002-05-29 |
| EP1147210A4 (en) | 2004-06-02 |
| MXPA01007805A (es) | 2003-06-04 |
| CN1345377A (zh) | 2002-04-17 |
| US6245921B1 (en) | 2001-06-12 |
| WO2000046388A1 (en) | 2000-08-10 |
| EP1147210A1 (en) | 2001-10-24 |
| TR200102232T2 (tr) | 2002-02-21 |
| CA2360840A1 (en) | 2000-08-10 |
| ZA200106057B (en) | 2002-07-24 |
| PL349153A1 (en) | 2002-07-01 |
| NO20013790D0 (no) | 2001-08-02 |
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