DE2842358C2 - - Google Patents
Info
- Publication number
- DE2842358C2 DE2842358C2 DE2842358A DE2842358A DE2842358C2 DE 2842358 C2 DE2842358 C2 DE 2842358C2 DE 2842358 A DE2842358 A DE 2842358A DE 2842358 A DE2842358 A DE 2842358A DE 2842358 C2 DE2842358 C2 DE 2842358C2
- Authority
- DE
- Germany
- Prior art keywords
- solution
- carbon atoms
- polar
- pseudomonic acid
- water
- 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.)
- Expired
Links
- 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 claims description 32
- MINDHVHHQZYEEK-HBBNESRFSA-N mupirocin Chemical compound 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 MINDHVHHQZYEEK-HBBNESRFSA-N 0.000 claims description 32
- 229960003128 mupirocin Drugs 0.000 claims description 32
- 229930194369 pseudomonic acid Natural products 0.000 claims description 32
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 239000003960 organic solvent Substances 0.000 claims description 14
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 12
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 9
- 239000013078 crystal Substances 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 9
- 238000002425 crystallisation Methods 0.000 claims description 8
- 230000008025 crystallization Effects 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 5
- 241000894006 Bacteria Species 0.000 claims description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 4
- 239000012043 crude product Substances 0.000 claims description 4
- 230000007935 neutral effect Effects 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- 125000005907 alkyl ester group Chemical group 0.000 claims description 3
- 150000001983 dialkylethers Chemical class 0.000 claims description 3
- 150000008282 halocarbons Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 238000010533 azeotropic distillation Methods 0.000 claims 1
- 239000000470 constituent Substances 0.000 claims 1
- 230000008020 evaporation Effects 0.000 claims 1
- 238000001704 evaporation Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 description 24
- 239000002904 solvent Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000012531 culture fluid Substances 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 241000589540 Pseudomonas fluorescens Species 0.000 description 4
- 239000006286 aqueous extract Substances 0.000 description 4
- 238000005119 centrifugation Methods 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000002274 desiccant Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000003495 polar organic solvent Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 229940072049 amyl acetate Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- -1 halogenated Hydrocarbon esters Chemical class 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000002255 vaccination 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
- C12P17/16—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
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
- C12N1/20—Bacteria; Culture media therefor
- C12N1/205—Bacterial isolates
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
- C12R2001/00—Microorganisms ; Processes using microorganisms
- C12R2001/01—Bacteria or Actinomycetales ; using bacteria or Actinomycetales
- C12R2001/38—Pseudomonas
- C12R2001/39—Pseudomonas fluorescens
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Biotechnology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Engineering & Computer Science (AREA)
- Microbiology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Biomedical Technology (AREA)
- Virology (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4067877 | 1977-09-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2842358A1 DE2842358A1 (de) | 1979-04-05 |
| DE2842358C2 true DE2842358C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1989-05-24 |
Family
ID=10416087
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19782842358 Granted DE2842358A1 (de) | 1977-09-30 | 1978-09-28 | Verfahren zur gewinnung von pseudomonsaeure |
Country Status (14)
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60243011A (ja) * | 1984-05-17 | 1985-12-03 | Seiwa Kasei:Kk | パ−マネントウエ−ブ用第１剤 |
| JPS60243010A (ja) * | 1984-05-17 | 1985-12-03 | Seiwa Kasei:Kk | 毛髪保護剤 |
| GB9026873D0 (en) * | 1990-12-11 | 1991-01-30 | Beecham Group Plc | Novel compounds |
| US5594026A (en) * | 1990-12-11 | 1997-01-14 | Smithkline Beecham Group P.L.C. | Polymorphs of crystalline mupirocin |
| MXPA01007805A (es) * | 1999-02-03 | 2003-06-04 | Biogal Gyogyszergyar | Proceso para la aislacion del acido pseudomonico a del caldo de cultivo que contiene un complejo de acido pseudomonico. . |
| IL144679A0 (en) | 1999-02-03 | 2002-06-30 | Teva Pharma | Process for the preparation of pseudomonic acid a antibiotic by microbiological method |
| TR200403211T3 (tr) | 2001-06-21 | 2005-02-21 | Biogal Gyogyszergyar Rt | Psödomonik asit üretimi için metabolik olarak kontrol edilen fermantasyon işlemi. |
| CN1625394A (zh) * | 2001-12-28 | 2005-06-08 | 拜奥盖尔药厂有限公司 | 结晶和无定形莫匹罗星钙的制备方法 |
| 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 |
| DE602005001753T2 (de) * | 2004-10-29 | 2008-05-21 | Uni-Chains A/S | Förderband mit seitlicher Faltung |
| EP1856111B1 (en) * | 2005-02-21 | 2014-01-29 | Syngen Biotech Co., Ltd. | Purification of mupirocin |
| GB2441328A (en) | 2006-08-30 | 2008-03-05 | Alpharma Aps | A method for obtaining mupirocin calcium |
| 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 |
| WO2022042299A1 (zh) | 2020-08-25 | 2022-03-03 | 杭州中美华东制药有限公司 | 一种莫匹罗星的提取方法 |
Family Cites Families (3)
| 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 |
| GB1565083A (en) * | 1976-02-20 | 1980-04-16 | Beecham Group Ltd | Pseudomonic acid amides |
-
1978
- 1978-09-27 CA CA312,240A patent/CA1103264A/en not_active Expired
- 1978-09-28 DE DE19782842358 patent/DE2842358A1/de active Granted
- 1978-09-28 IT IT51285/78A patent/IT1157197B/it active
- 1978-09-28 ZA ZA00785515A patent/ZA785515B/xx unknown
- 1978-09-28 FR FR7827765A patent/FR2404638A1/fr active Granted
- 1978-09-28 BE BE190787A patent/BE870855A/xx not_active IP Right Cessation
- 1978-09-29 DK DK433878A patent/DK152126C/da not_active IP Right Cessation
- 1978-09-29 IE IE1955/78A patent/IE47386B1/en not_active IP Right Cessation
- 1978-09-29 NL NL7809859A patent/NL7809859A/xx active Search and Examination
- 1978-09-29 US US05/946,873 patent/US4222942A/en not_active Expired - Lifetime
- 1978-09-29 ES ES473837A patent/ES473837A1/es not_active Expired
- 1978-09-29 CH CH1016178A patent/CH642366A5/de not_active IP Right Cessation
- 1978-09-30 JP JP12111878A patent/JPS5459281A/ja active Granted
- 1978-10-02 NZ NZ188559A patent/NZ188559A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES473837A1 (es) | 1979-10-16 |
| IE781955L (en) | 1979-03-30 |
| NZ188559A (en) | 1981-01-23 |
| JPS5459281A (en) | 1979-05-12 |
| US4222942A (en) | 1980-09-16 |
| CA1103264A (en) | 1981-06-16 |
| ZA785515B (en) | 1979-09-26 |
| AU4030478A (en) | 1980-04-03 |
| IT7851285A0 (it) | 1978-09-28 |
| AU531316B2 (en) | 1983-08-18 |
| CH642366A5 (de) | 1984-04-13 |
| IE47386B1 (en) | 1984-03-07 |
| DE2842358A1 (de) | 1979-04-05 |
| FR2404638A1 (fr) | 1979-04-27 |
| IT1157197B (it) | 1987-02-11 |
| DK152126B (da) | 1988-02-01 |
| FR2404638B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1982-04-16 |
| JPH032867B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1991-01-17 |
| NL7809859A (nl) | 1979-04-03 |
| DK433878A (da) | 1979-03-31 |
| DK152126C (da) | 1988-06-20 |
| BE870855A (fr) | 1979-03-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8128 | New person/name/address of the agent |
Representative=s name: JUNG, E., DIPL.-CHEM. DR.PHIL. SCHIRDEWAHN, J., DI |
|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition |