SK280255B6 - Spôsob izolácie lovastatínu - Google Patents
Spôsob izolácie lovastatínu Download PDFInfo
- Publication number
- SK280255B6 SK280255B6 SK1480-95A SK148095A SK280255B6 SK 280255 B6 SK280255 B6 SK 280255B6 SK 148095 A SK148095 A SK 148095A SK 280255 B6 SK280255 B6 SK 280255B6
- Authority
- SK
- Slovakia
- Prior art keywords
- lovastatin
- isolation
- lactone
- butyl acetate
- atcc
- 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 claims abstract description 46
- 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 claims abstract description 45
- 229960004844 lovastatin Drugs 0.000 title claims abstract description 45
- 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 claims abstract description 45
- 238000000034 method Methods 0.000 title claims abstract description 16
- 238000002955 isolation Methods 0.000 title claims abstract description 10
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000000855 fermentation Methods 0.000 claims abstract description 14
- 230000004151 fermentation Effects 0.000 claims abstract description 14
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000000706 filtrate Substances 0.000 claims abstract description 10
- 240000006439 Aspergillus oryzae Species 0.000 claims abstract description 8
- 235000002247 Aspergillus oryzae Nutrition 0.000 claims abstract description 8
- 241001465318 Aspergillus terreus Species 0.000 claims abstract description 8
- 244000005700 microbiome Species 0.000 claims description 6
- 241000233866 Fungi Species 0.000 claims description 3
- 241000228212 Aspergillus Species 0.000 claims 1
- 239000000284 extract Substances 0.000 abstract description 7
- 238000000605 extraction Methods 0.000 abstract description 6
- 238000002425 crystallisation Methods 0.000 abstract description 2
- 239000013543 active substance Substances 0.000 abstract 1
- 230000003247 decreasing effect Effects 0.000 abstract 1
- 230000000055 hyoplipidemic effect Effects 0.000 abstract 1
- 150000002596 lactones Chemical group 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000002253 acid Substances 0.000 description 11
- 229940043232 butyl acetate Drugs 0.000 description 11
- 239000002904 solvent Substances 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000012141 concentrate Substances 0.000 description 6
- 238000007273 lactonization reaction Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 235000015097 nutrients Nutrition 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
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 102100029077 3-hydroxy-3-methylglutaryl-coenzyme A reductase Human genes 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- BUBVLQDEIIUIQG-UHFFFAOYSA-N 3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-one Chemical compound C=1C=CC=CC=1COC1C(OCC=2C=CC=CC=2)C(OCC=2C=CC=CC=2)C(=O)OC1COCC1=CC=CC=C1 BUBVLQDEIIUIQG-UHFFFAOYSA-N 0.000 description 1
- 238000007445 Chromatographic isolation Methods 0.000 description 1
- 108090000895 Hydroxymethylglutaryl CoA Reductases Proteins 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 241000031003 Monascus ruber Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 108090000854 Oxidoreductases Proteins 0.000 description 1
- 102000004316 Oxidoreductases Human genes 0.000 description 1
- 239000003529 anticholesteremic agent Substances 0.000 description 1
- 229940127226 anticholesterol agent Drugs 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000005515 coenzyme Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229930000044 secondary metabolite Natural products 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 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 description 1
- 230000008719 thickening Effects 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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SI9300303A SI9300303A (en) | 1993-06-08 | 1993-06-08 | Process for isolation of hypolipemic effective substance |
| PCT/SI1994/000010 WO1994029292A1 (en) | 1993-06-08 | 1994-06-08 | Process for the isolation of lovastatin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK148095A3 SK148095A3 (en) | 1996-07-03 |
| SK280255B6 true SK280255B6 (sk) | 1999-10-08 |
Family
ID=20431195
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1480-95A SK280255B6 (sk) | 1993-06-08 | 1994-06-08 | Spôsob izolácie lovastatínu |
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 |
|---|---|---|---|---|
| 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. |
| MXPA06012251A (es) * | 2004-04-28 | 2006-12-15 | Unilever Nv | Aceite comestible que comprende estatinas. |
| TWI307360B (en) | 2004-12-03 | 2009-03-11 | Teva Gyogyszergyar Zartkoruen Mukodo Reszvenytarsasag | Process for constructing strain having compactin hydroxylation ability |
| 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 |
| US7872009B2 (en) * | 2005-11-21 | 2011-01-18 | Amgen Inc. | Beta-Secretase modulators and methods of use |
| WO2008137168A2 (en) * | 2007-05-07 | 2008-11-13 | True Charles W | Collapsible, stackable, semi-rigid universal tank for hazardous and non-hazardous goods |
| MX2009012608A (es) * | 2007-05-25 | 2009-12-07 | Amgen Inc | Compuestos de hidroxietil amina substituidos como moduladores de beta-secretasa y metodos de uso. |
| WO2008147547A1 (en) | 2007-05-25 | 2008-12-04 | Amgen Inc. | Substituted hydroxyethyl amine compounds as beta-secretase modulators and methods of use |
| US7803809B2 (en) * | 2008-11-12 | 2010-09-28 | Amgen Inc. | Substituted pyrano [2,3-b] pyridinamine compounds as beta-secretase modulators and methods of use |
| 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 |
| EP2288378A4 (en) * | 2008-04-16 | 2011-12-14 | Univ Utah Res Found | PHARMACOLOGICAL TARGETING OF VEGETABLE ILLNESS |
| CA2736130C (en) * | 2008-09-11 | 2014-01-14 | Amgen Inc. | Spiro-tetracyclic ring compounds as beta-secretase modulators and methods of use |
| IN2009MU00380A (cs) * | 2009-02-18 | 2010-04-02 | ||
| US8822485B2 (en) | 2009-11-23 | 2014-09-02 | Amgen Inc. | Amino heteroaryl compounds as beta-secretase modulators and methods of use |
| WO2011063233A1 (en) | 2009-11-23 | 2011-05-26 | Amgen Inc. | Amino heteroaryl compounds as beta-secretase modulators and methods of use |
| WO2011090911A1 (en) | 2010-01-19 | 2011-07-28 | Amgen Inc. | Amino heteroaryl compounds as beta-secretase modulators and methods of use |
| ES2450568T3 (es) | 2010-03-15 | 2014-03-25 | Amgen Inc. | Compuestos espiero de amino-dihidrooxazina y amino-dihidrotiazina como moduladores de beta-secretasa y su uso médico |
| CA2791281A1 (en) | 2010-03-15 | 2011-09-22 | Amgen Inc. | Spiro-tetracyclic ring compounds as beta-secretase modulators |
| 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 |
| WO2012019056A1 (en) | 2010-08-05 | 2012-02-09 | Amgen Inc. | Amino-iso-indole, amino-aza-iso-indole, amino-dihydroisoquinoline and amino-benzoxazine compounds as beta-secretase modulators and methods of use |
| 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 |
| CN102432573B (zh) * | 2011-12-26 | 2013-10-02 | 重庆大学 | 一种制备洛伐他汀的方法 |
| WO2014059185A1 (en) | 2012-10-12 | 2014-04-17 | Amgen Inc. | Amino - dihydrothiazine and amino - dioxido dihydrothiazine compounds as beta-secretase antagonists and methods of use |
| US9725469B2 (en) | 2012-11-15 | 2017-08-08 | Amgen, Inc. | Amino-oxazine and amino-dihydrothiazine compounds as beta-secretase modulators and methods of use |
| 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 |
| TW201446758A (zh) | 2013-03-01 | 2014-12-16 | Amgen Inc | 作爲β－分泌酶抑制劑的全氟化５，６－二氫－４Ｈ－１，３－□－２－胺化合物及其用途 |
| EP2964644B1 (en) | 2013-03-08 | 2018-12-26 | Amgen, Inc. | Perfluorinated cyclopropyl fused 1,3-oxazin-2-amine compounds as beta-secretase inhibitors and methods of use |
| 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 |
| EP3555084B1 (en) | 2016-12-15 | 2022-03-16 | Amgen Inc. | Thiazine derivatives as beta-secretase inhibitors and methods of use |
| JP7177773B2 (ja) | 2016-12-15 | 2022-11-24 | アムジエン・インコーポレーテツド | β－セクレターゼ阻害剤としてのオキサジン誘導体および使用方法 |
| MX387729B (es) | 2016-12-15 | 2025-03-18 | Amgen Inc | Derivados de dióxido de 1,4-tiazina y dióxido 1,2,4-tiadiazina como inhibidores de beta-secretasa y métodos de uso. |
| 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 |
|---|---|---|---|---|
| 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 |
| SI9300303A (en) | 1994-12-31 |
| 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 |
| 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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