HU210867B - Method for extraction and purification of mevinolin from culture medium - Google Patents
Method for extraction and purification of mevinolin from culture medium Download PDFInfo
- Publication number
- HU210867B HU210867B HU9203458A HU9203458A HU210867B HU 210867 B HU210867 B HU 210867B HU 9203458 A HU9203458 A HU 9203458A HU 9203458 A HU9203458 A HU 9203458A HU 210867 B HU210867 B HU 210867B
- Authority
- HU
- Hungary
- Prior art keywords
- active ingredient
- filtered
- mevinoline
- filtrate
- fermentation broth
- Prior art date
Links
- PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 title abstract description 5
- PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 title abstract description 4
- QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 title abstract description 3
- 238000000605 extraction Methods 0.000 title description 8
- 238000000746 purification Methods 0.000 title description 8
- 239000001963 growth medium Substances 0.000 title 1
- 239000004480 active ingredient Substances 0.000 claims abstract description 35
- 238000000855 fermentation Methods 0.000 claims abstract description 23
- 230000004151 fermentation Effects 0.000 claims abstract description 23
- 238000000034 method Methods 0.000 claims abstract description 19
- 239000002028 Biomass Substances 0.000 claims abstract description 13
- 238000001953 recrystallisation Methods 0.000 claims abstract description 9
- 238000004090 dissolution Methods 0.000 claims abstract description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 32
- 239000000706 filtrate Substances 0.000 claims description 21
- 239000000654 additive Substances 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 230000000996 additive effect Effects 0.000 claims description 9
- -1 alkyl acetate Chemical compound 0.000 claims description 6
- 238000000926 separation method Methods 0.000 claims description 4
- 239000002202 Polyethylene glycol Substances 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 229920001223 polyethylene glycol Polymers 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 229920001451 polypropylene glycol Polymers 0.000 claims description 2
- 150000003335 secondary amines Chemical class 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- 239000012530 fluid Substances 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- 238000001914 filtration Methods 0.000 abstract description 6
- 238000002955 isolation Methods 0.000 abstract description 3
- GJRQTCIYDGXPES-UHFFFAOYSA-N isobutyl acetate Chemical compound CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 20
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 150000001261 hydroxy acids Chemical group 0.000 description 8
- 150000002596 lactones Chemical group 0.000 description 8
- 239000012043 crude product Substances 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000012141 concentrate Substances 0.000 description 5
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 4
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 4
- 235000011130 ammonium sulphate Nutrition 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 241000228212 Aspergillus Species 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical group CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 238000011097 chromatography purification Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 241001465318 Aspergillus terreus Species 0.000 description 1
- ALOBUEHUHMBRLE-UHFFFAOYSA-N Ibutilide Chemical compound CCCCCCCN(CC)CCCC(O)C1=CC=C(NS(C)(=O)=O)C=C1 ALOBUEHUHMBRLE-UHFFFAOYSA-N 0.000 description 1
- 241000228347 Monascus <ascomycete fungus> Species 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000003570 biosynthesizing effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000003610 charcoal 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
- WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229960004053 ibutilide Drugs 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 229960004844 lovastatin Drugs 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000005406 washing 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
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/62—Carboxylic acid esters
-
- 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
- C12P17/06—Oxygen as only ring hetero atoms containing a six-membered hetero ring, e.g. fluorescein
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (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)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU9203458A HU210867B (en) | 1992-11-04 | 1992-11-04 | Method for extraction and purification of mevinolin from culture medium |
| PCT/HU1993/000051 WO1994010328A1 (en) | 1992-11-04 | 1993-09-08 | Process for the isolation and purification of mevinolin |
| DE4395515A DE4395515C2 (de) | 1992-11-04 | 1993-09-08 | Verfahren zur Isolierung und Reinigung von Mevinolin |
| ES09450018A ES2081776B1 (es) | 1992-11-04 | 1993-09-08 | Procedimiento para el aislamiento y purificacion de mevinolina. |
| DE4395515T DE4395515T1 (de) | 1992-11-04 | 1993-09-08 | Verfahren zur Isolierung und Reinigung von Mevinolin |
| AT0901593A AT401060B (de) | 1992-11-04 | 1993-09-08 | Verfahren zur isolierung und reinigung von mevinolin |
| CA002127381A CA2127381C (en) | 1992-11-04 | 1993-09-08 | Process for the isolation and purification of mevinolin |
| GR930100408A GR930100408A (el) | 1992-11-04 | 1993-10-18 | Μέ?οδος απομόνωσης και κα?αρισμού μεβινολίνης. |
| IT93MI002343A IT1266672B1 (it) | 1992-11-04 | 1993-11-04 | Procedimento per l'isolamento e la purificazione di mevinolina |
| US09/578,587 US6812007B1 (en) | 1992-11-04 | 2000-04-19 | Process for the isolation and purification of mevinolin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU9203458A HU210867B (en) | 1992-11-04 | 1992-11-04 | Method for extraction and purification of mevinolin from culture medium |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU210867B true HU210867B (en) | 1995-10-30 |
Family
ID=10982513
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU9203458A HU210867B (en) | 1992-11-04 | 1992-11-04 | Method for extraction and purification of mevinolin from culture medium |
Country Status (8)
| Country | Link |
|---|---|
| AT (1) | AT401060B (de) |
| CA (1) | CA2127381C (de) |
| DE (2) | DE4395515T1 (de) |
| ES (1) | ES2081776B1 (de) |
| GR (1) | GR930100408A (de) |
| HU (1) | HU210867B (de) |
| IT (1) | IT1266672B1 (de) |
| WO (1) | WO1994010328A1 (de) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI9300303A (en) * | 1993-06-08 | 1994-12-31 | Krka Tovarna Zdravil | Process for isolation of hypolipemic effective substance |
| CA2243592C (en) * | 1995-12-06 | 2001-12-25 | Antibiotic Co. | Method of production of lovastatin |
| SK282679B6 (sk) * | 1999-04-16 | 2002-11-06 | Biotika, A. S. | Spôsob izolácie lovastatínu z vyfermentovanej pôdy |
| YU63602A (sh) * | 2000-02-24 | 2006-01-16 | Biogal Gyogyszergyar Rt. | Postupak za prečišćavanje fermentacionog bujona |
| US6521762B2 (en) * | 2000-03-03 | 2003-02-18 | BIOGAL Gyógyszergyar RT. | Process for purifying lovastatin and simvastatin with reduced levels of dimeric impurities |
| ES2204285B1 (es) * | 2002-05-20 | 2005-03-01 | Ercros Industrial, S.A. | Procedimiento para el aislamiento y purificacion de lovastatina. |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5925599B2 (ja) * | 1979-02-20 | 1984-06-19 | 三共株式会社 | 新生理活性物質モナコリンｋおよびその製造法 |
| JPS55150898A (en) * | 1979-05-11 | 1980-11-25 | Sankyo Co Ltd | Preparation of a new physiologically active substance mb-530b |
| AU535944B2 (en) * | 1979-06-15 | 1984-04-12 | Merck & Co., Inc. | Hypocholestermic fermentation products from aspergillus |
| HU208997B (en) * | 1992-06-17 | 1994-02-28 | Gyogyszerkutato Intezet | Microbiological method for producing mevinoline |
-
1992
- 1992-11-04 HU HU9203458A patent/HU210867B/hu not_active IP Right Cessation
-
1993
- 1993-09-08 WO PCT/HU1993/000051 patent/WO1994010328A1/en not_active IP Right Cessation
- 1993-09-08 ES ES09450018A patent/ES2081776B1/es not_active Expired - Fee Related
- 1993-09-08 AT AT0901593A patent/AT401060B/de not_active IP Right Cessation
- 1993-09-08 DE DE4395515T patent/DE4395515T1/de active Pending
- 1993-09-08 CA CA002127381A patent/CA2127381C/en not_active Expired - Fee Related
- 1993-09-08 DE DE4395515A patent/DE4395515C2/de not_active Expired - Fee Related
- 1993-10-18 GR GR930100408A patent/GR930100408A/el not_active IP Right Cessation
- 1993-11-04 IT IT93MI002343A patent/IT1266672B1/it active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| WO1994010328A1 (en) | 1994-05-11 |
| IT1266672B1 (it) | 1997-01-09 |
| DE4395515C2 (de) | 1999-06-17 |
| ES2081776B1 (es) | 1996-10-16 |
| ATA901593A (de) | 1995-10-15 |
| AT401060B (de) | 1996-06-25 |
| DE4395515T1 (de) | 1994-12-01 |
| GR930100408A (el) | 1994-07-29 |
| ITMI932343A0 (it) | 1993-11-04 |
| CA2127381C (en) | 1997-12-23 |
| ES2081776A1 (es) | 1996-03-01 |
| ITMI932343A1 (it) | 1995-05-04 |
| CA2127381A1 (en) | 1994-05-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Lapse of definitive patent protection due to non-payment of fees |