SI9300303A - Process for isolation of hypolipemic effective substance - Google Patents
Process for isolation of hypolipemic effective substance Download PDFInfo
- Publication number
- SI9300303A SI9300303A SI9300303A SI9300303A SI9300303A SI 9300303 A SI9300303 A SI 9300303A SI 9300303 A SI9300303 A SI 9300303A SI 9300303 A SI9300303 A SI 9300303A SI 9300303 A SI9300303 A SI 9300303A
- Authority
- SI
- Slovenia
- Prior art keywords
- lovastatin
- atcc
- pct
- isolation
- lactone
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 13
- 230000000055 hyoplipidemic effect Effects 0.000 title claims abstract description 6
- 238000002955 isolation Methods 0.000 title abstract description 6
- 239000000126 substance Substances 0.000 title description 6
- 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 claims abstract description 25
- 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 claims abstract description 25
- 229960004844 lovastatin Drugs 0.000 claims abstract description 25
- 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 claims abstract description 25
- 238000000855 fermentation Methods 0.000 claims abstract description 14
- 230000004151 fermentation Effects 0.000 claims abstract description 14
- 241001465318 Aspergillus terreus Species 0.000 claims abstract description 9
- 240000006439 Aspergillus oryzae Species 0.000 claims abstract description 8
- 235000002247 Aspergillus oryzae Nutrition 0.000 claims abstract description 8
- 239000000706 filtrate Substances 0.000 claims abstract description 8
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims abstract description 7
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000013543 active substance Substances 0.000 claims abstract description 3
- 150000002596 lactones Chemical group 0.000 abstract description 13
- 238000000605 extraction Methods 0.000 abstract description 4
- 238000002425 crystallisation Methods 0.000 abstract 1
- 230000008025 crystallization Effects 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 7
- 238000007273 lactonization reaction Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 2
- 102100029077 3-hydroxy-3-methylglutaryl-coenzyme A reductase Human genes 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KJTLQQUUPVSXIM-ZCFIWIBFSA-N (R)-mevalonic acid Chemical compound OCC[C@](O)(C)CC(O)=O KJTLQQUUPVSXIM-ZCFIWIBFSA-N 0.000 description 1
- -1 3,5-dihydroxy-1-naphthalenheptanoic acid Chemical compound 0.000 description 1
- 101710158485 3-hydroxy-3-methylglutaryl-coenzyme A reductase Proteins 0.000 description 1
- KJTLQQUUPVSXIM-UHFFFAOYSA-N DL-mevalonic acid Natural products OCCC(O)(C)CC(O)=O KJTLQQUUPVSXIM-UHFFFAOYSA-N 0.000 description 1
- 108090000895 Hydroxymethylglutaryl CoA Reductases Proteins 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 241000228347 Monascus <ascomycete fungus> Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003529 anticholesteremic agent Substances 0.000 description 1
- 229940127226 anticholesterol agent Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/30—Oxygen atoms, e.g. delta-lactones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrane Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Steroid Compounds (AREA)
Priority Applications (14)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SI9300303A SI9300303A (en) | 1993-06-08 | 1993-06-08 | Process for isolation of hypolipemic effective substance |
HU9503385A HU216647B (hu) | 1993-06-08 | 1994-06-08 | Eljárás lovastatin izolálására |
RO95-02127A RO115444B1 (ro) | 1993-06-08 | 1994-06-08 | Procedeu pentru izolarea lovastatinului |
EP94917872A EP0702679B1 (en) | 1993-06-08 | 1994-06-08 | Process for the isolation of lovastatin |
CZ953251A CZ283540B6 (cs) | 1993-06-08 | 1994-06-08 | Způsob isolace lovastatinu |
PL94311880A PL178163B1 (pl) | 1993-06-08 | 1994-06-08 | Sposób izolowania lowastatyny |
US08/591,669 US5712130A (en) | 1993-06-08 | 1994-06-08 | Process for the isolation of lovastatin |
CA002164411A CA2164411C (en) | 1993-06-08 | 1994-06-08 | Process for the isolation of lovastatin |
AT94917872T ATE164842T1 (de) | 1993-06-08 | 1994-06-08 | Verfahren zur isolation von lovastatin |
RU96101191A RU2114912C1 (ru) | 1993-06-08 | 1994-06-08 | Способ выделения ловастатина |
SK1480-95A SK280255B6 (sk) | 1993-06-08 | 1994-06-08 | Spôsob izolácie lovastatínu |
DE69409516T DE69409516T2 (de) | 1993-06-08 | 1994-06-08 | Verfahren zur isolation von lovastatin |
PCT/SI1994/000010 WO1994029292A1 (en) | 1993-06-08 | 1994-06-08 | Process for the isolation of lovastatin |
BG100204A BG62852B1 (bg) | 1993-06-08 | 1995-12-08 | Метод за изолиране на ловастатин |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SI9300303A SI9300303A (en) | 1993-06-08 | 1993-06-08 | Process for isolation of hypolipemic effective substance |
Publications (1)
Publication Number | Publication Date |
---|---|
SI9300303A true SI9300303A (en) | 1994-12-31 |
Family
ID=20431195
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SI9300303A SI9300303A (en) | 1993-06-08 | 1993-06-08 | Process for isolation of hypolipemic effective substance |
Country Status (14)
Country | Link |
---|---|
US (1) | US5712130A (cs) |
EP (1) | EP0702679B1 (cs) |
AT (1) | ATE164842T1 (cs) |
BG (1) | BG62852B1 (cs) |
CA (1) | CA2164411C (cs) |
CZ (1) | CZ283540B6 (cs) |
DE (1) | DE69409516T2 (cs) |
HU (1) | HU216647B (cs) |
PL (1) | PL178163B1 (cs) |
RO (1) | RO115444B1 (cs) |
RU (1) | RU2114912C1 (cs) |
SI (1) | SI9300303A (cs) |
SK (1) | SK280255B6 (cs) |
WO (1) | WO1994029292A1 (cs) |
Families Citing this family (61)
Publication number | Priority date | Publication date | Assignee | Title |
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EA000954B1 (ru) * | 1995-12-06 | 2000-08-28 | Балканфарма - Разград Ад | Способ получения ловастатина |
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 |
WO1997037032A2 (en) * | 1996-03-28 | 1997-10-09 | Gist-Brocades B.V. | Preparation of microbial polyunsaturated fatty acid containing oil from pasteurised biomass |
US7238348B2 (en) * | 1996-09-30 | 2007-07-03 | Beijing Peking University Wbl Corporation Ltd. | Method of treatment of osteoporosis with compositions of red rice fermentation products |
US6046022A (en) * | 1996-09-30 | 2000-04-04 | Peking University | Methods and compositions employing red rice fermentation products |
EP0877089A1 (en) * | 1997-05-07 | 1998-11-11 | Gist-Brocades B.V. | HMG-CoA reductase inhibitor preparation process |
SK282679B6 (sk) * | 1999-04-16 | 2002-11-06 | Biotika, A. S. | Spôsob izolácie lovastatínu z vyfermentovanej pôdy |
US6372462B2 (en) | 1999-10-15 | 2002-04-16 | Medmyco Ltd. | Process for producing, methods and compositions of cholesterol lowering agents from higher basidiomycetes mushrooms |
DE60031447T2 (de) | 1999-11-30 | 2007-08-30 | Teva Gyogyszergyar Zartköruen Muködo Reszvenytarsasag | Verfahren zur rückgewinnung von statinverbindungen aus einer fermentationsbrühe |
PL364929A1 (en) * | 1999-12-14 | 2004-12-27 | Biogal Gyogyszergyar Rt. | Novel forms of pravastatin sodium |
IN191580B (cs) * | 1999-12-17 | 2003-12-06 | Ranbaxy Lab Ltd | |
HRP20020683A2 (en) * | 2000-02-24 | 2004-12-31 | Biogal Gyogyszergyar | Method of purifying a fermentation broth |
IN192861B (cs) * | 2000-06-30 | 2004-05-22 | Ranbaxy Lab Ltd | |
US20050215636A1 (en) * | 2000-10-05 | 2005-09-29 | Vilmos Keri | Pravastatin sodium substantially free of pravastatin lactone and EPI-pravastatin, and compositions containing same |
KR100379075B1 (en) * | 2002-03-07 | 2003-04-08 | Jinis Biopharmaceuticals Co | Method for producing low cholesterol animal food product and food product therefrom |
RU2309141C2 (ru) * | 2002-03-18 | 2007-10-27 | Байокон Лимитид | АМОРФНЫЕ ИНГИБИТОРЫ ГМГ-КоА-РЕДУКТАЗЫ И СПОСОБ ИХ ПОЛУЧЕНИЯ |
TWI319707B (en) * | 2003-11-24 | 2010-01-21 | Method of purifying pravastatin | |
US7777056B2 (en) * | 2004-03-30 | 2010-08-17 | Lupin Ltd. | Method for manufacture of 4-hydroxy pyran-2-one derivatives |
MXPA06012250A (es) * | 2004-04-28 | 2006-12-15 | Unilever Nv | Composicion que comprende estatinas. |
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EP1833780A1 (en) * | 2005-02-09 | 2007-09-19 | Teva Gyogyszergyár Zártköruen Muködo Részvenytarsaság | Methods of making pravastatin sodium |
US7838676B2 (en) * | 2005-11-21 | 2010-11-23 | Amgen Inc. | Beta-secretase modulators and methods of use |
US7745484B2 (en) * | 2005-11-21 | 2010-06-29 | Amgen Inc. | Beta-secretase modulators and methods of use |
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WO2009078033A2 (en) * | 2007-12-18 | 2009-06-25 | Themis Medicare Limited | Isolation and recovery of simvastatin in lactone form or in the form of an acid salt from the harvested fermentation broth |
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CN102344426A (zh) * | 2010-07-30 | 2012-02-08 | 北大方正集团有限公司 | 一种提取并纯化洛伐他汀的方法 |
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EP2643325A1 (en) | 2010-11-23 | 2013-10-02 | Amgen Inc. | Spiro-amino-imidazolone and spiro-amino-dihydro-pyrimidinone compounds as beta-secretase modulators and methods of use |
EP2673279A1 (en) | 2011-02-07 | 2013-12-18 | Amgen Inc. | 5-amino-oxazepine and 5-amino-thiazepane compounds as beta-secretase antagonists and methods of use |
US8962859B2 (en) | 2011-02-15 | 2015-02-24 | Amgen Inc. | Spiro-amino-imidazo-fused heterocyclic compounds as beta-secretase modulators and methods of use |
CN102993145B (zh) * | 2011-09-19 | 2015-06-03 | 北大方正集团有限公司 | 一种提取纯化洛伐他汀的方法 |
JP2014526560A (ja) | 2011-09-21 | 2014-10-06 | アムジエン・インコーポレーテツド | β‐セクレターゼ調節因子としてのアミノオキサジン化合物およびアミノジヒドロチアジン化合物および使用方法 |
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US9309263B2 (en) | 2013-01-29 | 2016-04-12 | Amgen Inc. | Fused multi-cyclic sulfone compounds as inhibitors of beta-secretase and methods of use thereof |
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US9096615B2 (en) * | 2013-07-30 | 2015-08-04 | Amgen Inc. | Bridged bicyclic amino thiazine dioxide compounds as inhibitors of beta-secretase and methods of use thereof |
WO2016022724A1 (en) | 2014-08-08 | 2016-02-11 | Amgen Inc. | Cyclopropyl fused thiazin-2-amine compounds as beta-secretase inhibitors and methods of use |
WO2017024180A1 (en) | 2015-08-06 | 2017-02-09 | Amgen Inc. | Vinyl fluoride cyclopropyl fused thiazin-2-amine compounds as beta-secretase inhibitors and methods of use |
CN106518824B (zh) * | 2016-09-30 | 2019-06-04 | 丽珠集团(宁夏)制药有限公司 | 一种洛伐他汀的提取工艺 |
CN106496174B (zh) * | 2016-09-30 | 2019-06-04 | 丽珠集团(宁夏)制药有限公司 | 一种洛伐他汀的提取精制工艺 |
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WO2018112084A1 (en) | 2016-12-15 | 2018-06-21 | Amgen Inc. | Bicyclic thiazine and oxazine derivatives as beta-secretase inhibitors and methods of use |
CA3047287A1 (en) | 2016-12-15 | 2018-06-21 | Amgen Inc. | Cyclopropyl fused thiazine derivatives as beta-secretase inhibitors and methods of use |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
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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 |
IL60219A (en) * | 1979-06-15 | 1985-05-31 | Merck & Co Inc | Hypocholesteremic fermentation products of the hmg-coa reductase inhibitor type,their preparation and pharmaceutical compositions containing them |
US4231938A (en) * | 1979-06-15 | 1980-11-04 | Merck & Co., Inc. | Hypocholesteremic fermentation products and process of preparation |
PT72394B (en) * | 1980-02-04 | 1982-09-06 | Merck & Co Inc | Process for preparing dihydro and tetrahydromevinoline hypocholesterolimics |
US4282155A (en) * | 1980-02-04 | 1981-08-04 | Merck & Co., Inc. | Antihypercholesterolemic compounds |
HU201577B (en) * | 1988-12-20 | 1990-11-28 | Gyogyszerkutato Intezet | Process for producing cyclosporin antibiotics |
NZ245713A (en) * | 1992-02-10 | 1994-12-22 | Novopharm Ltd | Production of the antibiotic lovastatin from genetically engineered aspergillus strains |
HU208997B (en) * | 1992-06-17 | 1994-02-28 | Gyogyszerkutato Intezet | Microbiological method for producing mevinoline |
HU210867B (en) * | 1992-11-04 | 1995-10-30 | Biogal Gyogyszergyar | Method for extraction and purification of mevinolin from culture medium |
-
1993
- 1993-06-08 SI SI9300303A patent/SI9300303A/sl not_active IP Right Cessation
-
1994
- 1994-06-08 AT AT94917872T patent/ATE164842T1/de not_active IP Right Cessation
- 1994-06-08 WO PCT/SI1994/000010 patent/WO1994029292A1/en active IP Right Grant
- 1994-06-08 CZ CZ953251A patent/CZ283540B6/cs not_active IP Right Cessation
- 1994-06-08 US US08/591,669 patent/US5712130A/en not_active Expired - Fee Related
- 1994-06-08 RO RO95-02127A patent/RO115444B1/ro unknown
- 1994-06-08 PL PL94311880A patent/PL178163B1/pl not_active IP Right Cessation
- 1994-06-08 SK SK1480-95A patent/SK280255B6/sk unknown
- 1994-06-08 HU HU9503385A patent/HU216647B/hu not_active IP Right Cessation
- 1994-06-08 CA CA002164411A patent/CA2164411C/en not_active Expired - Fee Related
- 1994-06-08 DE DE69409516T patent/DE69409516T2/de not_active Expired - Fee Related
- 1994-06-08 EP EP94917872A patent/EP0702679B1/en not_active Expired - Lifetime
- 1994-06-08 RU RU96101191A patent/RU2114912C1/ru not_active IP Right Cessation
-
1995
- 1995-12-08 BG BG100204A patent/BG62852B1/bg unknown
Also Published As
Publication number | Publication date |
---|---|
WO1994029292A1 (en) | 1994-12-22 |
SK148095A3 (en) | 1996-07-03 |
CA2164411C (en) | 2002-01-15 |
PL178163B1 (pl) | 2000-03-31 |
ATE164842T1 (de) | 1998-04-15 |
EP0702679A1 (en) | 1996-03-27 |
EP0702679B1 (en) | 1998-04-08 |
RO115444B1 (ro) | 2000-02-28 |
CZ283540B6 (cs) | 1998-04-15 |
DE69409516D1 (de) | 1998-05-14 |
HUT72836A (en) | 1996-05-28 |
HU216647B (hu) | 1999-07-28 |
BG100204A (bg) | 1996-06-28 |
PL311880A1 (en) | 1996-03-18 |
US5712130A (en) | 1998-01-27 |
CZ325195A3 (en) | 1996-04-17 |
SK280255B6 (sk) | 1999-10-08 |
DE69409516T2 (de) | 1998-11-19 |
CA2164411A1 (en) | 1994-12-22 |
HU9503385D0 (en) | 1996-01-29 |
RU2114912C1 (ru) | 1998-07-10 |
BG62852B1 (bg) | 2000-09-29 |
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