HU210867B - Method for extraction and purification of mevinolin from culture medium - Google Patents

Method for extraction and purification of mevinolin from culture medium Download PDF

Info

Publication number: HU210867B
Authority: HU; Hungary
Prior art keywords: active ingredient; filtered; mevinoline; filtrate; fermentation broth
Prior art date: 1992-11-04

Application number

HU9203458A

Other languages

English (en)

Hungarian (hu)

Inventor

Antalne Dr Jekkel

Imre Moravcsik

Attila Andor

Lajos Deak

Istvan Szabo

Attila Jakab

Vilmos Keri

Laszlo Eszenyi

Laszlone Kovacs

Gyulane Sztaray

Irma Hoegye

Imre Szekely

Ilkoey Eva Dr

Forgacs Ilona Bagdine

Ambrus Gabor Dr

Balint Janos Dr

Balogh Zsuzsanna Scheidlne

Deline Dr Konszky Etelka Dr

Horvath Gyula Dr

Csaba Szabo

Ildiko Lang

Szabolcs Matyas

Original Assignee

Biogal Gyogyszergyar

Priority date (The priority date 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 date listed.)

1992-11-04

Filing date

1992-11-04

Publication date

1995-10-30

1992-11-04 Application filed by Biogal Gyogyszergyar filed Critical Biogal Gyogyszergyar

1992-11-04 Priority to HU9203458A priority Critical patent/HU210867B/hu

1993-09-08 Priority to ES09450018A priority patent/ES2081776B1/es

1993-09-08 Priority to AT0901593A priority patent/AT401060B/de

1993-09-08 Priority to DE4395515T priority patent/DE4395515T1/de

1993-09-08 Priority to PCT/HU1993/000051 priority patent/WO1994010328A1/fr

1993-09-08 Priority to CA002127381A priority patent/CA2127381C/fr

1993-09-08 Priority to DE4395515A priority patent/DE4395515C2/de

1993-10-18 Priority to GR930100408A priority patent/GR930100408A/el

1993-11-04 Priority to IT93MI002343A priority patent/IT1266672B1/it

1995-10-30 Publication of HU210867B publication Critical patent/HU210867B/hu

2000-04-19 Priority to US09/578,587 priority patent/US6812007B1/en

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)

HU9203458A 1992-11-04 1992-11-04 Method for extraction and purification of mevinolin from culture medium HU210867B (en)

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
ES09450018A ES2081776B1 (es)	1992-11-04	1993-09-08	Procedimiento para el aislamiento y purificacion de mevinolina.
AT0901593A AT401060B (de)	1992-11-04	1993-09-08	Verfahren zur isolierung und reinigung von mevinolin
DE4395515T DE4395515T1 (de)	1992-11-04	1993-09-08	Verfahren zur Isolierung und Reinigung von Mevinolin
PCT/HU1993/000051 WO1994010328A1 (fr)	1992-11-04	1993-09-08	Procede d'isolement et de purification de mevinoline
CA002127381A CA2127381C (fr)	1992-11-04	1993-09-08	Procede d'isolement et de purification de la mevinoline
DE4395515A DE4395515C2 (de)	1992-11-04	1993-09-08	Verfahren zur Isolierung und Reinigung von 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 (fr)
CA (1)	CA2127381C (fr)
DE (2)	DE4395515C2 (fr)
ES (1)	ES2081776B1 (fr)
GR (1)	GR930100408A (fr)
HU (1)	HU210867B (fr)
IT (1)	IT1266672B1 (fr)
WO (1)	WO1994010328A1 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
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
EA000954B1 (ru) *	1995-12-06	2000-08-28	Балканфарма - Разград Ад	Способ получения ловастатина
SK282679B6 (sk) *	1999-04-16	2002-11-06	Biotika, A. S.	Spôsob izolácie lovastatínu z vyfermentovanej pôdy
HRP20020683A2 (en) *	2000-02-24	2004-12-31	Biogal Gyogyszergyar	Method of purifying a fermentation broth
CA2402061A1 (fr) *	2000-03-03	2001-09-13	Vilmos Keri	Procede de purification de lovastatine et de simvastatine pour la reduction de la teneur en impuretes dimeres
ES2204285B1 (es) *	2002-05-20	2005-03-01	Ercros Industrial, S.A.	Procedimiento para el aislamiento y purificacion de lovastatina.

Family Cites Families (4)

* Cited by examiner, † Cited by third party
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
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
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 DE DE4395515A patent/DE4395515C2/de not_active Expired - Fee Related
- 1993-09-08 WO PCT/HU1993/000051 patent/WO1994010328A1/fr not_active Ceased
- 1993-09-08 DE DE4395515T patent/DE4395515T1/de active Pending
- 1993-09-08 AT AT0901593A patent/AT401060B/de not_active IP Right Cessation
- 1993-09-08 ES ES09450018A patent/ES2081776B1/es not_active Expired - Fee Related
- 1993-09-08 CA CA002127381A patent/CA2127381C/fr 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
AT401060B (de)	1996-06-25
CA2127381C (fr)	1997-12-23
ES2081776B1 (es)	1996-10-16
ITMI932343A1 (it)	1995-05-04
ATA901593A (de)	1995-10-15
WO1994010328A1 (fr)	1994-05-11
ITMI932343A0 (it)	1993-11-04
DE4395515T1 (de)	1994-12-01
CA2127381A1 (fr)	1994-05-11
GR930100408A (el)	1994-07-29
IT1266672B1 (it)	1997-01-09
ES2081776A1 (es)	1996-03-01
DE4395515C2 (de)	1999-06-17

Legal Events

Date	Code	Title	Description
2006-08-28	MM4A	Lapse of definitive patent protection due to non-payment of fees

Publication	Publication Date	Title
RU2081121C1 (ru)	1997-06-10	Способ получения клавулановой кислоты или ее фармацевтически приемлемых солей или эфиров, соль клавулановой кислоты с амином
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RU2088586C1 (ru)	1997-08-27	Способ получения клавулановой кислоты или ее фармацевтически приемлемых солей или эфиров
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