SK10932001A3 - Mikrobiálny spôsob výroby pravastatínu - Google Patents
Mikrobiálny spôsob výroby pravastatínu Download PDFInfo
- Publication number
- SK10932001A3 SK10932001A3 SK1093-2001A SK10932001A SK10932001A3 SK 10932001 A3 SK10932001 A3 SK 10932001A3 SK 10932001 A SK10932001 A SK 10932001A SK 10932001 A3 SK10932001 A3 SK 10932001A3
- Authority
- SK
- Slovakia
- Prior art keywords
- formula
- compound
- pravastatin
- medium
- culture
- Prior art date
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- 230000007483 microbial process Effects 0.000 title claims abstract description 7
- 229960002965 pravastatin Drugs 0.000 title claims description 126
- TUZYXOIXSAXUGO-UHFFFAOYSA-N Pravastatin Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(O)C=C21 TUZYXOIXSAXUGO-UHFFFAOYSA-N 0.000 title claims description 123
- TUZYXOIXSAXUGO-PZAWKZKUSA-N pravastatin Chemical compound C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 TUZYXOIXSAXUGO-PZAWKZKUSA-N 0.000 title claims description 113
- 238000004519 manufacturing process Methods 0.000 title description 17
- 238000000034 method Methods 0.000 claims abstract description 56
- 241000235575 Mortierella Species 0.000 claims abstract description 45
- 150000001875 compounds Chemical class 0.000 claims abstract description 40
- 238000000855 fermentation Methods 0.000 claims abstract description 35
- 230000004151 fermentation Effects 0.000 claims abstract description 35
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 33
- 230000008569 process Effects 0.000 claims abstract description 23
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 6
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 5
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 5
- 235000015097 nutrients Nutrition 0.000 claims abstract description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 114
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 102
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 63
- 239000002609 medium Substances 0.000 claims description 61
- 239000000243 solution Substances 0.000 claims description 55
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 45
- VGMFHMLQOYWYHN-UHFFFAOYSA-N Compactin Natural products OCC1OC(OC2C(O)C(O)C(CO)OC2Oc3cc(O)c4C(=O)C(=COc4c3)c5ccc(O)c(O)c5)C(O)C(O)C1O VGMFHMLQOYWYHN-UHFFFAOYSA-N 0.000 claims description 44
- AJLFOPYRIVGYMJ-UHFFFAOYSA-N SJ000287055 Natural products C12C(OC(=O)C(C)CC)CCC=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 AJLFOPYRIVGYMJ-UHFFFAOYSA-N 0.000 claims description 44
- BOZILQFLQYBIIY-UHFFFAOYSA-N mevastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CCC=C21 BOZILQFLQYBIIY-UHFFFAOYSA-N 0.000 claims description 44
- 239000000758 substrate Substances 0.000 claims description 44
- AJLFOPYRIVGYMJ-INTXDZFKSA-N mevastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=CCC[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 AJLFOPYRIVGYMJ-INTXDZFKSA-N 0.000 claims description 43
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 39
- -1 secondary amine salt Chemical class 0.000 claims description 38
- 239000000203 mixture Substances 0.000 claims description 25
- 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 claims description 21
- 239000008103 glucose Substances 0.000 claims description 21
- 239000007864 aqueous solution Substances 0.000 claims description 19
- 239000000725 suspension Substances 0.000 claims description 19
- 239000000706 filtrate Substances 0.000 claims description 18
- 239000000284 extract Substances 0.000 claims description 17
- 238000005805 hydroxylation reaction Methods 0.000 claims description 17
- 239000001963 growth medium Substances 0.000 claims description 15
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 15
- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical class C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 claims description 13
- 150000002596 lactones Chemical class 0.000 claims description 12
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- 239000002253 acid Substances 0.000 claims description 10
- 238000002955 isolation Methods 0.000 claims description 10
- 150000003335 secondary amines Chemical class 0.000 claims description 10
- 238000001179 sorption measurement Methods 0.000 claims description 10
- 238000004587 chromatography analysis Methods 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 8
- 239000001888 Peptone Substances 0.000 claims description 8
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 claims description 8
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical group CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 claims description 8
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 claims description 8
- 108010080698 Peptones Proteins 0.000 claims description 7
- 239000008346 aqueous phase Substances 0.000 claims description 7
- 235000019319 peptone Nutrition 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- 229940041514 candida albicans extract Drugs 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 238000000605 extraction Methods 0.000 claims description 6
- 229960001495 pravastatin sodium Drugs 0.000 claims description 6
- 230000009466 transformation Effects 0.000 claims description 6
- 239000012138 yeast extract Substances 0.000 claims description 6
- 102000008109 Mixed Function Oxygenases Human genes 0.000 claims description 5
- 108010074633 Mixed Function Oxygenases Proteins 0.000 claims description 5
- 235000019764 Soybean Meal Nutrition 0.000 claims description 5
- 239000003957 anion exchange resin Substances 0.000 claims description 5
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 5
- 238000002844 melting Methods 0.000 claims description 5
- 230000008018 melting Effects 0.000 claims description 5
- 159000000000 sodium salts Chemical class 0.000 claims description 5
- 239000004455 soybean meal Substances 0.000 claims description 5
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 4
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical class C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 claims description 4
- 229930091371 Fructose Natural products 0.000 claims description 4
- 239000005715 Fructose Substances 0.000 claims description 4
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims description 4
- 239000006286 aqueous extract Substances 0.000 claims description 4
- 235000011187 glycerol Nutrition 0.000 claims description 4
- 239000012074 organic phase Substances 0.000 claims description 4
- 239000005018 casein Substances 0.000 claims description 3
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 claims description 3
- 235000021240 caseins Nutrition 0.000 claims description 3
- 238000012258 culturing Methods 0.000 claims description 3
- LAWOZCWGWDVVSG-UHFFFAOYSA-N dioctylamine Chemical class CCCCCCCCNCCCCCCCC LAWOZCWGWDVVSG-UHFFFAOYSA-N 0.000 claims description 3
- 230000002538 fungal effect Effects 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 235000013372 meat Nutrition 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 claims description 2
- 229920003053 polystyrene-divinylbenzene Polymers 0.000 claims description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
- VWBQYTRBTXKKOG-IYNICTALSA-M pravastatin sodium Chemical compound [Na+].C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC([O-])=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 VWBQYTRBTXKKOG-IYNICTALSA-M 0.000 claims 4
- 125000005907 alkyl ester group Chemical group 0.000 claims 3
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 claims 1
- 238000011033 desalting Methods 0.000 claims 1
- 238000005227 gel permeation chromatography Methods 0.000 claims 1
- 239000002002 slurry Substances 0.000 claims 1
- 238000000746 purification Methods 0.000 abstract description 5
- 238000000926 separation method Methods 0.000 abstract description 3
- 241000894007 species Species 0.000 abstract description 3
- 238000010564 aerobic fermentation Methods 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 20
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 20
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
- 229920001817 Agar Polymers 0.000 description 16
- 239000008272 agar Substances 0.000 description 16
- 239000008367 deionised water Substances 0.000 description 16
- 229910021641 deionized water Inorganic materials 0.000 description 16
- 238000003756 stirring Methods 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000012071 phase Substances 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 13
- 239000012141 concentrate Substances 0.000 description 13
- OQARDMYXSOFTLN-PZAWKZKUSA-N pravastatin lactone Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 OQARDMYXSOFTLN-PZAWKZKUSA-N 0.000 description 13
- 230000001954 sterilising effect Effects 0.000 description 12
- 238000004659 sterilization and disinfection Methods 0.000 description 12
- 239000002024 ethyl acetate extract Substances 0.000 description 11
- 239000013028 medium composition Substances 0.000 description 11
- 238000004809 thin layer chromatography Methods 0.000 description 11
- 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 10
- 230000033444 hydroxylation Effects 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000011780 sodium chloride Substances 0.000 description 10
- 241000233866 Fungi Species 0.000 description 8
- 239000012043 crude product Substances 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
- 238000010828 elution Methods 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 5
- 230000001965 increasing effect Effects 0.000 description 5
- 230000000813 microbial effect Effects 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- 241000873620 Mortierella thaxteri Species 0.000 description 4
- RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 4
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- RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- PDBXRGUGLTUAAD-ABPOPGQRSA-M sodium;(3r)-7-[(1s,2s,8s,8ar)-2-methyl-8-[(2s)-2-methylbutanoyl]oxy-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3-hydroxyheptanoate Chemical class [Na+].C1=C[C@H](C)[C@H](CCCC[C@@H](O)CC([O-])=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)CCC=C21 PDBXRGUGLTUAAD-ABPOPGQRSA-M 0.000 description 4
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-
- 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
- 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
- C12N1/14—Fungi; Culture media therefor
- C12N1/145—Fungal isolates
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- 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
- C12R2001/645—Fungi ; Processes using fungi
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Health & Medical Sciences (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Microbiology (AREA)
- Biochemistry (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Mycology (AREA)
- Botany (AREA)
- Medicinal Chemistry (AREA)
- Tropical Medicine & Parasitology (AREA)
- Virology (AREA)
- Biomedical Technology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11845899P | 1999-02-03 | 1999-02-03 | |
| US13475999P | 1999-05-18 | 1999-05-18 | |
| PCT/US2000/002993 WO2000046175A1 (en) | 1999-02-03 | 2000-02-03 | Microbial process for preparing pravastatin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK10932001A3 true SK10932001A3 (sk) | 2002-06-04 |
Family
ID=26816384
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1093-2001A SK10932001A3 (sk) | 1999-02-03 | 2000-02-03 | Mikrobiálny spôsob výroby pravastatínu |
Country Status (27)
| Country | Link |
|---|---|
| EP (1) | EP1154979B1 (enExample) |
| JP (2) | JP3645491B2 (enExample) |
| KR (2) | KR20060061406A (enExample) |
| CN (3) | CN1177793C (enExample) |
| AR (2) | AR023368A1 (enExample) |
| AT (1) | ATE294771T1 (enExample) |
| AU (2) | AU774438B2 (enExample) |
| BG (1) | BG105778A (enExample) |
| BR (1) | BR0009180A (enExample) |
| CA (1) | CA2361701C (enExample) |
| CZ (1) | CZ20012761A3 (enExample) |
| DE (1) | DE60019898T2 (enExample) |
| ES (1) | ES2240072T3 (enExample) |
| HK (1) | HK1042686B (enExample) |
| HR (1) | HRP20010577B1 (enExample) |
| HU (1) | HUP0200650A3 (enExample) |
| IL (1) | IL144697A0 (enExample) |
| IS (1) | IS6036A (enExample) |
| MX (1) | MXPA01007807A (enExample) |
| NO (1) | NO20013818L (enExample) |
| PL (1) | PL350317A1 (enExample) |
| PT (1) | PT1154979E (enExample) |
| RU (1) | RU2004127981A (enExample) |
| SK (1) | SK10932001A3 (enExample) |
| TR (2) | TR200600009T2 (enExample) |
| WO (1) | WO2000046175A1 (enExample) |
| YU (1) | YU55701A (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI20305A (sl) † | 1999-08-06 | 2001-02-28 | LEK, tovarna farmacevtskih in kemi�nih izdelkov, d.d. | Kristali natrijeve soli pravastatina |
| EP1798214A3 (en) * | 1999-11-30 | 2007-08-01 | Teva Gyogyszergyár Zártköruen Muködo Részvenytarsaság | Process for recovering statin compounds from a fermentation broth |
| AU1804601A (en) * | 1999-11-30 | 2001-06-12 | Biogal Gyogyszergyar Rt | Process for recovering statin compounds from a fermentation broth |
| KR20020062340A (ko) | 1999-12-14 | 2002-07-25 | 비오갈 기오기스제르갸르 알티. | 신규 형태의 프라바스타틴 나트륨 |
| HRP20030347A2 (en) * | 2000-10-05 | 2005-04-30 | Teva Gy�gyszergy�r R�szv�nyt�rsas�g | Pravastatin sodium substantially free of pravastatin lactone and epi-pravastatin, and compositions containing same |
| JP2003026634A (ja) * | 2001-07-17 | 2003-01-29 | Mercian Corp | プラバスタチンナトリウム塩の製造方法 |
| JP3463875B2 (ja) | 2001-08-06 | 2003-11-05 | 三共株式会社 | プラバスタチンを精製する方法 |
| JP3422791B2 (ja) | 2002-08-06 | 2003-06-30 | 三共株式会社 | プラバスタチンの単離・精製方法 |
| KR100540761B1 (ko) * | 2002-08-09 | 2006-01-16 | 코바이오텍 (주) | 프라바스타틴 나트륨의 제조방법 |
| EP1452519A1 (en) * | 2003-02-25 | 2004-09-01 | Balkanpharma-Razgrad AD | Method for the isolation and purification of pravastatin sodium |
| WO2004096785A1 (ja) * | 2003-04-25 | 2004-11-11 | Nippon Chemiphar Co., Ltd. | （２s，３s）－３－［［（１s）－１－イソブトキシメチル－３－メチルブチル］カルバモイル］オキシラン－２－カルボン酸の塩 |
| CN1244688C (zh) | 2003-07-09 | 2006-03-08 | 上海天伟生物制药有限公司 | 生产普伐他汀钠的微生物和方法 |
| TWI319707B (en) | 2003-11-24 | 2010-01-21 | Method of purifying pravastatin | |
| TWI307360B (en) | 2004-12-03 | 2009-03-11 | Teva Gyogyszergyar Zartkoruen Mukodo Reszvenytarsasag | Process for constructing strain having compactin hydroxylation ability |
| US20110130450A1 (en) * | 2008-04-02 | 2011-06-02 | Aad Johannes Bouman | Pravastatin extraction |
| EP3714959A1 (en) * | 2019-03-29 | 2020-09-30 | Basf Se | Isolation of small molecules from the fermentation broth of a eukaryotic microorganism |
| CN117164541B (zh) * | 2022-05-27 | 2025-09-30 | 黑龙江华瑞生物科技有限公司 | 一种从美伐他汀母液中分离纯化美伐他汀的方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE249514T1 (de) * | 1996-03-28 | 2003-09-15 | Dsm Ip Assets Bv | Verfahren zur herstellung von granulärer mikrobieller biomasse und gewinnung wertvoller komponenten aus mikrobieller biomasse |
-
2000
- 2000-02-03 AT AT00911709T patent/ATE294771T1/de not_active IP Right Cessation
- 2000-02-03 MX MXPA01007807A patent/MXPA01007807A/es unknown
- 2000-02-03 JP JP2000597248A patent/JP3645491B2/ja not_active Expired - Fee Related
- 2000-02-03 HR HR20010577A patent/HRP20010577B1/xx not_active IP Right Cessation
- 2000-02-03 KR KR1020067009407A patent/KR20060061406A/ko not_active Ceased
- 2000-02-03 TR TR2006/00009T patent/TR200600009T2/xx unknown
- 2000-02-03 BR BR0009180-4A patent/BR0009180A/pt not_active Application Discontinuation
- 2000-02-03 CN CNB008058792A patent/CN1177793C/zh not_active Expired - Fee Related
- 2000-02-03 CA CA002361701A patent/CA2361701C/en not_active Expired - Fee Related
- 2000-02-03 HU HU0200650A patent/HUP0200650A3/hu unknown
- 2000-02-03 IL IL14469700A patent/IL144697A0/xx not_active IP Right Cessation
- 2000-02-03 CZ CZ20012761A patent/CZ20012761A3/cs unknown
- 2000-02-03 DE DE60019898T patent/DE60019898T2/de not_active Expired - Fee Related
- 2000-02-03 TR TR2001/03127T patent/TR200103127T2/xx unknown
- 2000-02-03 HK HK02103449.9A patent/HK1042686B/en not_active IP Right Cessation
- 2000-02-03 AU AU33567/00A patent/AU774438B2/en not_active Ceased
- 2000-02-03 CN CNA2004100456608A patent/CN1590363A/zh active Pending
- 2000-02-03 ES ES00911709T patent/ES2240072T3/es not_active Expired - Lifetime
- 2000-02-03 PT PT00911709T patent/PT1154979E/pt unknown
- 2000-02-03 KR KR1020017009821A patent/KR100648541B1/ko not_active Expired - Fee Related
- 2000-02-03 YU YU55701A patent/YU55701A/sh unknown
- 2000-02-03 WO PCT/US2000/002993 patent/WO2000046175A1/en not_active Ceased
- 2000-02-03 CN CNB2003101233833A patent/CN1260344C/zh not_active Expired - Fee Related
- 2000-02-03 PL PL00350317A patent/PL350317A1/xx unknown
- 2000-02-03 SK SK1093-2001A patent/SK10932001A3/sk unknown
- 2000-02-03 EP EP00911709A patent/EP1154979B1/en not_active Expired - Lifetime
- 2000-02-04 AR ARP000100484A patent/AR023368A1/es unknown
-
2001
- 2001-08-02 IS IS6036A patent/IS6036A/is unknown
- 2001-08-03 NO NO20013818A patent/NO20013818L/no not_active Application Discontinuation
- 2001-08-03 BG BG105778A patent/BG105778A/bg unknown
-
2004
- 2004-09-01 JP JP2004254575A patent/JP4197312B2/ja not_active Expired - Fee Related
- 2004-09-22 RU RU2004127981/04A patent/RU2004127981A/ru not_active Application Discontinuation
- 2004-09-24 AU AU2004214559A patent/AU2004214559A1/en not_active Abandoned
-
2007
- 2007-06-29 AR ARP070102941A patent/AR061765A2/es not_active Application Discontinuation
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