JP2002535977A5 - - Google Patents
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- Publication number
- JP2002535977A5 JP2002535977A5 JP2000597248A JP2000597248A JP2002535977A5 JP 2002535977 A5 JP2002535977 A5 JP 2002535977A5 JP 2000597248 A JP2000597248 A JP 2000597248A JP 2000597248 A JP2000597248 A JP 2000597248A JP 2002535977 A5 JP2002535977 A5 JP 2002535977A5
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- JP
- Japan
- Prior art keywords
- formula
- compound
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- culture
- solution
- 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.)
- Granted
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- 238000000034 method Methods 0.000 claims 31
- 150000001875 compounds Chemical class 0.000 claims 22
- 241000235575 Mortierella Species 0.000 claims 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 12
- -1 secondary amine salt Chemical class 0.000 claims 7
- 239000000243 solution Substances 0.000 claims 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 244000005700 microbiome Species 0.000 claims 6
- 239000003960 organic solvent Substances 0.000 claims 6
- 239000002253 acid Substances 0.000 claims 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 4
- 239000007864 aqueous solution Substances 0.000 claims 4
- 238000000855 fermentation Methods 0.000 claims 4
- 230000004151 fermentation Effects 0.000 claims 4
- 150000002596 lactones Chemical class 0.000 claims 4
- 239000002609 medium Substances 0.000 claims 4
- 239000011347 resin Substances 0.000 claims 4
- 229920005989 resin Polymers 0.000 claims 4
- 239000000758 substrate Substances 0.000 claims 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 3
- 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 claims 3
- 229910052783 alkali metal Inorganic materials 0.000 claims 3
- 150000001340 alkali metals Chemical group 0.000 claims 3
- 125000005907 alkyl ester group Chemical group 0.000 claims 3
- 239000003957 anion exchange resin Substances 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- 239000000284 extract Substances 0.000 claims 3
- 239000000706 filtrate Substances 0.000 claims 3
- 239000001963 growth medium Substances 0.000 claims 3
- 230000000640 hydroxylating effect Effects 0.000 claims 3
- 239000011259 mixed solution Substances 0.000 claims 3
- 229960002965 pravastatin Drugs 0.000 claims 3
- 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 claims 3
- 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 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 2
- 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 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 2
- 241000047703 Nonion Species 0.000 claims 2
- 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 2
- 239000008346 aqueous phase Substances 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 239000013078 crystal Substances 0.000 claims 2
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 claims 2
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical group CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 claims 2
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 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 2
- 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 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 239000012074 organic phase Substances 0.000 claims 2
- 238000000926 separation method Methods 0.000 claims 2
- 159000000000 sodium salts Chemical group 0.000 claims 2
- 239000000725 suspension Substances 0.000 claims 2
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical class C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 claims 1
- 229930091371 Fructose Natural products 0.000 claims 1
- 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 1
- 239000005715 Fructose Substances 0.000 claims 1
- 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 1
- 102000008109 Mixed Function Oxygenases Human genes 0.000 claims 1
- 108010074633 Mixed Function Oxygenases Proteins 0.000 claims 1
- 239000001888 Peptone Substances 0.000 claims 1
- 108010080698 Peptones Proteins 0.000 claims 1
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 claims 1
- 235000019764 Soybean Meal Nutrition 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 239000006286 aqueous extract Substances 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 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 1
- 230000036983 biotransformation Effects 0.000 claims 1
- 229940041514 candida albicans extract Drugs 0.000 claims 1
- 239000005018 casein Substances 0.000 claims 1
- 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 1
- 235000021240 caseins Nutrition 0.000 claims 1
- 238000004587 chromatography analysis Methods 0.000 claims 1
- 238000012258 culturing Methods 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 238000011033 desalting Methods 0.000 claims 1
- LAWOZCWGWDVVSG-UHFFFAOYSA-N dioctylamine Chemical class CCCCCCCCNCCCCCCCC LAWOZCWGWDVVSG-UHFFFAOYSA-N 0.000 claims 1
- 238000010828 elution Methods 0.000 claims 1
- LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 claims 1
- 238000000605 extraction Methods 0.000 claims 1
- 238000005227 gel permeation chromatography Methods 0.000 claims 1
- 239000008103 glucose Substances 0.000 claims 1
- 235000011187 glycerol Nutrition 0.000 claims 1
- 238000004128 high performance liquid chromatography Methods 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 235000013372 meat Nutrition 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- 230000002906 microbiologic effect Effects 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 235000015097 nutrients Nutrition 0.000 claims 1
- 235000019319 peptone Nutrition 0.000 claims 1
- 239000012071 phase Substances 0.000 claims 1
- 229920003053 polystyrene-divinylbenzene Polymers 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 125000001453 quaternary ammonium group Chemical group 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 150000003335 secondary amines Chemical class 0.000 claims 1
- 238000001179 sorption measurement Methods 0.000 claims 1
- 239000004455 soybean meal Substances 0.000 claims 1
- 241000894007 species Species 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- 239000012138 yeast extract Substances 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11845899P | 1999-02-03 | 1999-02-03 | |
| US60/118,458 | 1999-02-03 | ||
| US13475999P | 1999-05-18 | 1999-05-18 | |
| US60/134,759 | 1999-05-18 | ||
| PCT/US2000/002993 WO2000046175A1 (en) | 1999-02-03 | 2000-02-03 | Microbial process for preparing pravastatin |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004254575A Division JP4197312B2 (ja) | 1999-02-03 | 2004-09-01 | プラバスタチンナトリウム |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002535977A JP2002535977A (ja) | 2002-10-29 |
| JP3645491B2 JP3645491B2 (ja) | 2005-05-11 |
| JP2002535977A5 true JP2002535977A5 (enExample) | 2005-11-04 |
Family
ID=26816384
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000597248A Expired - Fee Related JP3645491B2 (ja) | 1999-02-03 | 2000-02-03 | プラバスタチンの微生物学的製法 |
| JP2004254575A Expired - Fee Related JP4197312B2 (ja) | 1999-02-03 | 2004-09-01 | プラバスタチンナトリウム |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004254575A Expired - Fee Related JP4197312B2 (ja) | 1999-02-03 | 2004-09-01 | プラバスタチンナトリウム |
Country Status (27)
| Country | Link |
|---|---|
| EP (1) | EP1154979B1 (enExample) |
| JP (2) | JP3645491B2 (enExample) |
| KR (2) | KR100648541B1 (enExample) |
| CN (3) | CN1260344C (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) | TR200103127T2 (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 |
| RU2002114072A (ru) | 1999-11-30 | 2004-07-20 | Биогал Джиоджисзерджиар РТ (HU) | Способ выделения соединений статина из ферментационного бульона |
| EP1798214A3 (en) * | 1999-11-30 | 2007-08-01 | Teva Gyogyszergyár Zártköruen Muködo Részvenytarsaság | Process for recovering statin compounds from a fermentation broth |
| CA2394200C (en) | 1999-12-14 | 2006-10-03 | Biogal Gyogyszergyar Rt. | Novel forms of pravastatin sodium |
| IL155194A0 (en) * | 2000-10-05 | 2003-11-23 | Biogal Pharmaceutical Co Ltd | 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 |
| EP1619190B1 (en) * | 2003-04-25 | 2010-12-29 | Nippon Chemiphar Co., Ltd. | Salts of (2s,3s)-3- [[(1s)-1-isobutoxymethyl-3-methylbutyl]carbamoyl] oxirane-2-carboxylic acid |
| 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 |
| DE202004020671U1 (de) | 2003-11-24 | 2005-12-08 | Teva Gyogyszergyar Reszvenytarsasag | 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 |
|---|---|---|---|---|
| DE69724782T3 (de) * | 1996-03-28 | 2015-12-24 | Dsm Ip Assets B.V. | Verfahren zur Herstellung von granulärer mikrobieller Biomasse und Gewinnung wertvoller Komponenten aus mikrobieller Biomasse |
-
2000
- 2000-02-03 IL IL14469700A patent/IL144697A0/xx not_active IP Right Cessation
- 2000-02-03 WO PCT/US2000/002993 patent/WO2000046175A1/en not_active Ceased
- 2000-02-03 EP EP00911709A patent/EP1154979B1/en not_active Expired - Lifetime
- 2000-02-03 KR KR1020017009821A patent/KR100648541B1/ko not_active Expired - Fee Related
- 2000-02-03 CN CNB2003101233833A patent/CN1260344C/zh not_active Expired - Fee Related
- 2000-02-03 TR TR2001/03127T patent/TR200103127T2/xx unknown
- 2000-02-03 AU AU33567/00A patent/AU774438B2/en not_active Ceased
- 2000-02-03 BR BR0009180-4A patent/BR0009180A/pt not_active Application Discontinuation
- 2000-02-03 ES ES00911709T patent/ES2240072T3/es not_active Expired - Lifetime
- 2000-02-03 SK SK1093-2001A patent/SK10932001A3/sk unknown
- 2000-02-03 CZ CZ20012761A patent/CZ20012761A3/cs unknown
- 2000-02-03 HU HU0200650A patent/HUP0200650A3/hu unknown
- 2000-02-03 PL PL00350317A patent/PL350317A1/xx unknown
- 2000-02-03 KR KR1020067009407A patent/KR20060061406A/ko not_active Ceased
- 2000-02-03 HR HR20010577A patent/HRP20010577B1/xx not_active IP Right Cessation
- 2000-02-03 DE DE60019898T patent/DE60019898T2/de not_active Expired - Fee Related
- 2000-02-03 PT PT00911709T patent/PT1154979E/pt unknown
- 2000-02-03 JP JP2000597248A patent/JP3645491B2/ja not_active Expired - Fee Related
- 2000-02-03 CN CNA2004100456608A patent/CN1590363A/zh active Pending
- 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 MX MXPA01007807A patent/MXPA01007807A/es unknown
- 2000-02-03 YU YU55701A patent/YU55701A/sh unknown
- 2000-02-03 HK HK02103449.9A patent/HK1042686B/en not_active IP Right Cessation
- 2000-02-03 AT AT00911709T patent/ATE294771T1/de not_active IP Right Cessation
- 2000-02-03 TR TR2006/00009T patent/TR200600009T2/xx unknown
- 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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