WO2012041218A1 - 一种环脂肽化合物或其盐的纯化方法 - Google Patents
一种环脂肽化合物或其盐的纯化方法 Download PDFInfo
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- WO2012041218A1 WO2012041218A1 PCT/CN2011/080220 CN2011080220W WO2012041218A1 WO 2012041218 A1 WO2012041218 A1 WO 2012041218A1 CN 2011080220 W CN2011080220 W CN 2011080220W WO 2012041218 A1 WO2012041218 A1 WO 2012041218A1
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- Prior art keywords
- formula
- adsorption resin
- compound
- xad
- organic solvent
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- SGDUNWOGDLDRIJ-ZUEIMRROSA-N CC([C@H](CC1)CC1NC)N Chemical compound CC([C@H](CC1)CC1NC)N SGDUNWOGDLDRIJ-ZUEIMRROSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/14—Extraction; Separation; Purification
- C07K1/16—Extraction; Separation; Purification by chromatography
- C07K1/22—Affinity chromatography or related techniques based upon selective absorption processes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/14—Extraction; Separation; Purification
- C07K1/16—Extraction; Separation; Purification by chromatography
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/50—Cyclic peptides containing at least one abnormal peptide link
- C07K7/54—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring
- C07K7/56—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring the cyclisation not occurring through 2,4-diamino-butanoic acid
Definitions
- the present invention relates to the field of organic chemistry, and more particularly to a method for purifying a cyclolipopeptide compound or a salt thereof as shown in Formula I. Background technique
- Fungal infections have become a major cause of high morbidity and mortality in immunodeficient patients. The incidence of mold infections has increased significantly over the past 20 years. High-risk populations of fungal infections include critically ill patients, surgical patients, and those with HIV infection, blood cancer, and other oncological diseases. Those who have undergone organ transplants are also at high risk for fungal infections.
- echinococcal is effective in treating infections caused by Candida or Aspergillus.
- These drugs are represented by caspofungin and micafungin.
- Echinoglobin inhibits fungi by inhibiting the formation of 1, 3-beta glycosidic bonds, thereby reducing harm to the human body, reducing side effects as much as possible while efficient, so they are in use Safer than traditional antifungal drugs.
- FK463 (Micafungin) is a compound of the formula III, which is a compound of the formula II, FR901379 (Mo), which is obtained by cleavage of a side chain to obtain a compound of the formula I FR179642 (MJ, and then a method of adding a side chain by synthesis) So, to get high purity micafungin, high purity formula I
- the bacterium of the genus Streptomyces is Streptomyces anulatus 481 1 strain, Streptomyces cerevisiae 8703 strain, Streptomyces ( Streptomyces sp.) strain No. 6907, and IF013244, IF06798, IF031963, IF09951, NRRL 12052 and the like. No.
- 5,376,634 discloses a method for converting a compound of the formula II into a compound of the formula I by enzymatic reaction, first filtering the transformant, preliminarily purifying it through an activated carbon column, and further purifying it on a silica gel column, and concentrating under reduced pressure to obtain a white solid.
- This method uses a large amount of organic solvent, and the activated carbon and silica gel used cannot be recycled, which easily causes environmental pollution, and seriously affects the health of the operator, and is not suitable for industrial mass production.
- the present invention is directed to a method of purifying a compound of formula I.
- the present invention provides a method of purifying a compound of formula I or a salt thereof, the method comprising the steps of:
- the macroporous adsorption resin is selected from the group consisting of: a nonpolar aromatic adsorption resin obtained by polymerizing styrene and divinylbenzene, or a medium having a methacrylate unit structure.
- a nonpolar aromatic adsorption resin obtained by polymerizing styrene and divinylbenzene
- a medium having a methacrylate unit structure e.g., a nonpolar aromatic adsorption resin obtained by polymerizing styrene and divinylbenzene
- a medium having a methacrylate unit structure e.g., a methacrylate unit structure
- the adsorption resin is selected from the group consisting of: XAD-1, XAD-2, XAD-3, XAD-4,
- the adsorption resin is an adsorption resin containing a halogen element and chemically bonding a styrene polymerization substrate.
- the adsorption resin is a bromine-containing element to chemically bond a styrene polymer group.
- Body adsorption resin is a bromine-containing element to chemically bond a styrene polymer group.
- the adsorption resin is selected from the group consisting of SP-207, SP207SS or a mixture thereof.
- the step (1) is a step of flowing a solution containing a crude compound of the formula I through a chromatography column loaded with a macroporous adsorption resin or a solution containing a crude compound of the formula I and a macroporous adsorption resin. 1 ⁇ The crude product of the formula I was loaded to a macroporous adsorption resin; the flow rate of 0. 1 - 10 bed volume per hour.
- the solution containing the crude compound of the formula I contains an ionizable salt;
- the macroporous adsorption resin is selected from the group consisting of non-polar aromatic adsorption resins obtained by polymerizing styrene and divinylbenzene. Or a medium polarity methacrylic acid adsorption resin having a methacrylate unit structure; ionizable salts including sulfates, nitrates, salts containing 3 ⁇ 4, phosphates, acetates, carbonates, citrates, Silicate, persulfate, chromate, lactate, oxalate, etc., or mixtures thereof.
- the volume percentage of the organic solvent is from 0 to 3%, preferably from 0 to 2%, based on the total volume of the washing liquid.
- the volume percentage of the organic solvent is from 0 to 20%, preferably from 0 to 5%, based on the total volume of the eluent.
- the weight ratio of the crude compound of the formula I to the macroporous adsorption resin is from 0.1 to 15 (g/L); preferably from 5 to 10 (g/L). .
- the organic solvent is selected from the group consisting of CH alcohol and CH ketone; preferably, the organic solvent is selected from the group consisting of methanol, ethanol, propanol, butanol, acetone, methyl ethyl ketone, or a mixture thereof; optimally selected from the group consisting of methanol, ethanol or acetone. Accordingly, the present invention provides a purification method which does not require a large amount of solvent and does not use silica gel, overcomes the drawbacks existing in the prior art, and at the same time improves the purity of the compound of formula I. DRAWINGS
- Figure 1 shows the HPLC chromatogram of crude 1 of the compound of formula 1 of Example 1.
- Figure 2 shows the HPLC chromatogram of the purified compound of formula I in Example 6.
- aromatic macroporous adsorption resins are used, especially For the aromatic-derived resin, for example, bromine is bonded to an aromatic skeleton. It enhances the hydrophobic adsorption force and has a strong adsorption capacity for the highly hydrophilic substance of the compound of the formula I, and has a very remarkable effect in purifying the compound of the formula I and its related impurities.
- a common non-polar aromatic adsorption resin composed of styrene and divinylbenzene is used, or a medium-polar methacrylic acid adsorption resin having a methacrylate unit structure, the hydrophobic adsorption force is weak.
- the highly hydrophilic substance of the compound of the formula I has a low adsorption capacity, and the inventors creatively add an ionizable salt to the hydrophobicity of the target substance when the compound of the formula I is adsorbed to the macroporous adsorption resin.
- the compound of formula I is more readily adsorbed onto the resin for the purpose of purifying the compound of formula I.
- the method for purifying a compound of formula I provided by the present invention comprises the steps of:
- the crude compound of the formula I is applied to the macroporous adsorption resin
- water, an organic solvent, or a mixed solution of an organic solvent and water is used as a washing liquid to wash the macroporous adsorption resin;
- a compound of the formula I is eluted from the macroporous adsorption resin by using water, an organic solvent, or a mixed solution of an organic solvent and water as an eluent.
- the first step can be achieved by contacting a solution containing the crude compound of formula I with a macroporous adsorption resin.
- the contact may be a.
- the adsorption resin is directly introduced into a solution containing the crude compound of the formula I, and then stirred for 5 to 120 minutes; or b.
- the adsorption resin is placed in a chromatography apparatus such as a chromatography column to make the content
- the solution of the crude compound of the compound I flows through the column at a flow rate of 0.1 to 10 bed volumes per hour.
- the purification method comprises the steps of:
- the adsorption resin is directly put into a solution containing the crude compound of the formula I, and then stirred for 5 to 120 minutes;
- step C using a mixed solution of water, an organic solvent, or an organic solvent and water as a washing liquid to wash the macroporous resin remaining in the step B;
- the separation described in the step B includes filtration, centrifugation or the like to separate the resin from the filtrate.
- the organic solvent is selected from the group consisting of ( 4 alcohols, d- 4 ketones or mixtures thereof, preferably from methanol, ethanol, propanol, butanol, acetone, methyl ethyl ketone or their mixture.
- the adsorption resin is selected from the group consisting of: a non-polar aliphatic adsorption resin obtained by polymerizing styrene and divinylbenzene or a medium polarity having a methacrylate unit structure.
- Methacrylic acid adsorption resin Preferably, it is: XAD series adsorption resin produced by RohmHaas, USA, and D i a on HP series adsorption resin produced by Mitsubishi Chemical Corporation of Japan and an adsorption resin containing bromine element to chemically bond styrene polymerization matrix.
- the author of the present invention found in the present invention that the adsorption resin containing a halogen-containing element to bond a styrene polymerizable substrate with a chemical bond has higher adsorption power and separation efficiency.
- An adsorption resin containing a bromine element to chemically bond a styrene polymer matrix is preferred, and the most preferred adsorption resin is SP207, SP207 S S or a mixture thereof.
- adsorbent resins containing a halogen-containing element to chemically bond a styrene polymer matrix mainly based on Mitsubishi Chemical's SP207, SP207 S S, but not limited to these two types of resins.
- the above first step is to mix the crude compound of formula I with an ionizable salt prior to loading the crude compound of formula I to increase the conductivity of the sample and the hydrophobicity of the target compound of formula I. , enhancing the adsorption capacity of the resin to the target compound.
- Ionizable salts include sulfates, nitrates, salts containing 3 ⁇ 4, phosphates, acetates, carbonates, citrates, silicates, persulphates, chromates, lactates, oxalates, etc. , or their compounds.
- the concentration of the organic solvent in the washing liquid is
- Ionizable salts include sulfates, nitrates, salts containing 3 ⁇ 4, phosphates, acetates, carbonates, citrates, silicates, persulphates, chromates, lactates, oxalates, etc. , or a mixture of them. Preference is given to mixing from one or more of the most common salts described below: salts, sulphates, phosphates, acetates, carbonates and citrates. Most preferred: NaCl, KC1 and Wo (NH 4 ) 2 S0 4 .
- the concentration of the organic solvent in the eluate is from 0% to 20%, preferably from 0% to 5%.
- the washing can be carried out 1, 2, or 3 times.
- the washing speed is 0. 1-10 bed volumes per hour.
- the elution rate is 0. 1-10 bed volumes per hour.
- pharmaceutically acceptable salt refers to a salt formed from a base selected from the group consisting of inorganic bases such as sodium, potassium, magnesium, calcium, aluminum, and the like; and organic bases such as methylamine, ethylamine, monoethanolamine.
- purity of a compound as shown in Formula I As used herein, “purity of a compound as shown in Formula I", “purity of a compound of formula I” or “HPLC purity of a compound of formula I” are used interchangeably and refer to the high performance liquid chromatography (HPLC) provided by the present invention.
- HPLC high performance liquid chromatography
- crude product of the compound of formula I can be obtained using methods available in the art, such as, but not limited to, by the method described in Example 1 of EP0431350B1, The strain was fermented by Coleophoma sp. F- 11899 (FERM BP2635), and then the cells were extracted with an organic solvent. Preferably, the fermentation broth is directly added to two volumes of organic solvent for extraction.
- Preferred organic solvents are selected from the group consisting of: methanol, ethanol or acetone.
- a solution containing a crude product of a compound of formula I or "a solution containing a crude product of a compound of formula I” is used interchangeably and refers to a compound of the formula I and one or more non-target compounds.
- the solution may be obtained by dissolving the crude compound of the formula I in water or a buffer solution, or it may be a reaction solution of a compound of the formula I obtained in any procedure.
- the reaction solution of the compound of the formula I obtained by the method for preparing the compound of the formula I which is available in the art can be used, see Example 1 of CN1040541C.
- a solution obtained by adding a certain amount of water or an organic solvent to the post-conversion liquid containing the compound of formula I is from 0% to 2%.
- loading refers to the process of contacting a crude solution of a compound of formula I with a macroporous adsorption resin to adsorb a crude product of a compound of formula I onto a macroporous adsorption resin.
- the contacting includes directly introducing the macroporous adsorption resin into the solution and then agitating the adsorption; and loading the macroporous adsorption resin into the chromatography device to flow the solution through the chromatography column.
- Wash buffer refers to a buffer used to wash (primarily organic phase) macroporous adsorption resin prior to elution of the target compound of formula I.
- the wash buffer and the loading buffer can be of the same polarity, but this is not required.
- the "eluting" of the molecule from the macroporous adsorption resin means removing the molecule from the macroporous adsorption resin by changing the polarity of the buffer around the macroporous adsorption resin. This polarity enables the buffer to compete with the molecule for macroporous adsorption. Adsorption site on the resin.
- elution buffer is used to elute the target compound I from the solid phase.
- the elution buffer allows the target compound I to elute from the macroporous adsorption resin.
- “Purifying" a compound of formula I from a composition comprising a compound of the formula I and one or more non-target compounds means increasing the composition of the composition by removing (completely or partially) at least one non-target compound from the composition. The purity of the compound I.
- the present invention provides a novel and inexpensive method for purifying cyclolipopeptide compounds, particularly echinocandin compounds.
- the purification step of the method provided by the invention has the characteristics of short route, mild condition, high purification yield, very small amount of organic solvent used, simple treatment, small environmental pollution, etc., and the process is greatly reduced. Operation and equipment requirements reduce production costs.
- the method provided by the invention can obtain a relatively stable target product, is beneficial to the quality control of the final product, and is advantageous for industrialized large production.
- the invention is further illustrated below in conjunction with specific embodiments. It is to be understood that the examples are not intended to limit the scope of the invention.
- the experimental methods in which the specific conditions are not indicated in the following examples are usually carried out according to conventional conditions or according to the conditions recommended by the manufacturer. All percentages, ratios, ratios, or parts are by weight unless otherwise indicated.
- the unit of weight percent by volume in the present invention is well known to those skilled in the art and, for example, refers to the weight of the solute in a 100 ml solution.
- HPLC purity is 73. 91%.
- the solution of the compound of formula I is 7. 3g / L, HPLC purity is 73. 91%. See Figure 1 and Table 1 for the HPLC profile. Table 1
- the crude solution was loaded onto a column containing 300 mL of SP207 SS resin at a loading rate of 5 bed volumes per hour. After the loading was completed, 2 column volumes were washed with 1% ethanol, the washing flow rate was 1 bed volume per hour, 2 column volumes were washed with 2% ethanol, and the washing flow rate was 1 bed volume per hour. After washing, 3.6 L of 3% ethanol was used as an eluent, and the elution flow rate was 1 bed volume per hour. The fraction containing the compound of formula I was collected and mixed. 0% ⁇ The purity of the mixture is 99.0% (yield 94.2%), the purity is 99.0%. HPLC map see Figure 2 and Table 2.
- the crude solution was loaded onto a column containing 600 mL of SP207SS resin at a flow rate of 5 bed volumes per hour. After the end of the loading, 2 column volumes were washed with purified water at a flow rate of 1 bed volume per hour. After washing, 7.2 L of 2% ethanol was used as an eluent, and the elution flow rate was 2 bed volumes per hour. The fraction containing the compound of formula I was collected and mixed. The content of the compound of formula I is 4. 4 g (yield 95.6%), and the purity is 99.0%.
- the crude solution was loaded onto a chromatography column containing 46 L of SP207 resin at a flow rate of 5 bed volumes per hour. After the end of the loading, 2 column volumes were washed with purified water at a flow rate of 1 bed volume per hour. After washing, 150 L of 20% ethanol was used as an eluent, and the elution flow rate was 2 bed volumes per hour. The fraction containing the compound of formula I was collected and mixed. 1% ⁇ The content of the compound of the formula I was 4. 0g (yield 87.4%), the purity was 98.1%.
- the crude solution was loaded onto a column containing 460 mL of SP207 resin at a flow rate of 5 bed volumes per hour. After the loading was completed, 2 column volumes were washed with 1% ethanol, and the washing flow rate was 1 bed volume per hour. After washing, using 3. 0 L of 5% ethanol as an eluent, the elution flow rate was 1 bed volume per hour, and the fraction containing the compound of formula I was collected and mixed. The content of the compound of the formula I was 4. 4 g (yield 95.6%), and the purity was 97.9%. Comparative Example 1
- the crude solution was applied to a column packed with 0.8 L of XAD-16 resin at a flow rate of 1 bed volume per hour. After the loading was completed, 5 column volumes were washed with pure water at a washing flow rate of 1 bed volume per hour. After washing, the elution flow rate was 1 bed volume per hour with 2.5 L 3% methanol as an eluent, and the fraction containing the compound of formula I was collected and mixed. The 5%.
- the purity of the compound is 6. 6g (yield 50.4%), the purity is 79. 5%.
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Abstract
Description
Claims
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ES11828114.6T ES2581562T3 (es) | 2010-09-29 | 2011-09-27 | Procedimiento para purificar compuestos lipopeptídicos cíclicos o sales de los mismos |
KR1020137010894A KR101514903B1 (ko) | 2010-09-29 | 2011-09-27 | 사이클릭 리포펩타이드 화합물 또는 그의 염의 정제방법 |
JP2013530549A JP6000254B2 (ja) | 2010-09-29 | 2011-09-27 | 環状リポペプチド化合物又はその塩の精製方法 |
CA2813330A CA2813330A1 (en) | 2010-09-29 | 2011-09-27 | Process for purifying cyclolipopeptide compounds or the salts thereof |
RU2013118532/04A RU2535489C1 (ru) | 2010-09-29 | 2011-09-27 | Способ очистки циклолипопептидных соединений или их солей |
US13/877,427 US8927690B2 (en) | 2010-09-29 | 2011-09-27 | Process for purifying cyclolipopeptide compounds or the salts thereof |
EP11828114.6A EP2623511B1 (en) | 2010-09-29 | 2011-09-27 | Process for purifying cyclic lipopeptide compounds or salts thereof |
AU2011307731A AU2011307731B2 (en) | 2010-09-29 | 2011-09-27 | Process for purifying cyclic lipopeptide compounds or salts thereof |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201010297406.2 | 2010-09-29 | ||
CN201010297406 | 2010-09-29 |
Publications (1)
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WO2012041218A1 true WO2012041218A1 (zh) | 2012-04-05 |
Family
ID=45891956
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/CN2011/080220 WO2012041218A1 (zh) | 2010-09-29 | 2011-09-27 | 一种环脂肽化合物或其盐的纯化方法 |
Country Status (10)
Country | Link |
---|---|
US (1) | US8927690B2 (zh) |
EP (1) | EP2623511B1 (zh) |
JP (1) | JP6000254B2 (zh) |
KR (1) | KR101514903B1 (zh) |
CN (1) | CN102432674B (zh) |
AU (1) | AU2011307731B2 (zh) |
CA (1) | CA2813330A1 (zh) |
ES (1) | ES2581562T3 (zh) |
RU (1) | RU2535489C1 (zh) |
WO (1) | WO2012041218A1 (zh) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2012143293A1 (en) * | 2011-04-20 | 2012-10-26 | Xellia Pharmaceuticals Aps | Method for purification of micafungin |
US8927690B2 (en) | 2010-09-29 | 2015-01-06 | Shanghai Techwell Biopharmaceutical Co., Ltd. | Process for purifying cyclolipopeptide compounds or the salts thereof |
US20150065417A1 (en) * | 2012-03-30 | 2015-03-05 | Shanghai Techwell Biophamaceutical Co., Ltd. | High purity cyclopeptide compound as well as preparation method and use thereof |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2623611B1 (en) * | 2010-09-30 | 2016-07-13 | Shanghai Techwell Biopharmaceutical Co., Ltd | Method for purifying cyclic lipopeptide or salt thereof |
CN102627689B (zh) * | 2012-03-30 | 2014-08-06 | 上海天伟生物制药有限公司 | 一种环肽类化合物的水合物及其制备方法和用途 |
CN102911257B (zh) * | 2012-09-21 | 2014-02-12 | 无锡市第四人民医院 | 环脂肽类抗生素及其制备和应用 |
CN104418940A (zh) * | 2013-08-28 | 2015-03-18 | 重庆乾泰生物医药有限公司 | 一种高纯度环己肽类化合物的制备方法 |
CN103965298B (zh) * | 2014-05-23 | 2016-08-10 | 浙江海正药业股份有限公司 | 一种阿尼芬净的纯化方法 |
CN104926701B (zh) * | 2015-06-30 | 2017-05-03 | 西安蓝晓科技新材料股份有限公司 | 一种蛋氨酸纯化的工艺 |
SG11201805618UA (en) * | 2015-12-31 | 2018-07-30 | Dev Ct Biotechnology | Process for preparing a crassocephalum crepidioides extract, extract prepared thereby and use of the extract |
CN106755221A (zh) * | 2016-11-28 | 2017-05-31 | 无锡福祈制药有限公司 | 一种米卡芬净母核fr179642的制备方法 |
CN111434675A (zh) * | 2019-01-11 | 2020-07-21 | 苏州纳微科技股份有限公司 | 一种米卡芬净母环的分离纯化方法 |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4874843A (en) * | 1987-12-03 | 1989-10-17 | Eli Lilly And Company | Chromatographic purification process |
EP0486011A2 (en) * | 1990-11-16 | 1992-05-20 | Fujisawa Pharmaceutical Co., Ltd. | Pharmaceutical composition against Pneumocystis carinii |
US5376634A (en) | 1990-06-18 | 1994-12-27 | Fujisawa Pharmaceutical Co., Ltd. | Polypeptide compound and a process for preparation thereof |
EP0431350B1 (en) | 1989-11-13 | 1995-07-26 | Fujisawa Pharmaceutical Co., Ltd. | New polypeptide compound and a process for preparation thereof |
EP1197557A1 (en) * | 1999-07-02 | 2002-04-17 | Fujisawa Pharmaceutical Co., Ltd. | Gene encoding cyclic lipopeptide acylase and expression of the same |
EP1137663B1 (en) * | 1998-12-09 | 2006-08-30 | Eli Lilly And Company | Purification of echinocandin cyclopeptide compounds |
US20100249371A1 (en) * | 2009-03-24 | 2010-09-30 | Cadila Healthcare Limited | Purification process for lipopeptides |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5378804A (en) * | 1993-03-16 | 1995-01-03 | Merck & Co., Inc. | Aza cyclohexapeptide compounds |
US5552521A (en) * | 1995-02-10 | 1996-09-03 | Merck & Co., Inc. | Process for preparing certain aza cyclohexapeptides |
EP0933422A4 (en) * | 1996-06-13 | 2005-02-02 | Fujisawa Pharmaceutical Co | CYCLIC LIPOPEPTIDE ACYLASE |
US6960360B2 (en) | 2000-08-31 | 2005-11-01 | Phenolics, Llc | Efficient method for producing compositions enriched in total phenols |
WO2002068456A1 (en) | 2001-02-26 | 2002-09-06 | Fujisawa Pharmaceutical Co., Ltd. | Echinocandin derivatives, pharmaceutical compositions containing same and use thereof as drugs |
DE102004060750A1 (de) * | 2004-12-15 | 2006-07-13 | Sanofi-Aventis Deutschland Gmbh | Verfahren zur Deacylierung von Lipopeptiden |
CN102432674B (zh) | 2010-09-29 | 2014-01-22 | 上海天伟生物制药有限公司 | 一种环脂肽化合物或其盐的纯化方法 |
EP2623611B1 (en) * | 2010-09-30 | 2016-07-13 | Shanghai Techwell Biopharmaceutical Co., Ltd | Method for purifying cyclic lipopeptide or salt thereof |
-
2011
- 2011-09-27 CN CN201110290430.8A patent/CN102432674B/zh active Active
- 2011-09-27 KR KR1020137010894A patent/KR101514903B1/ko active IP Right Grant
- 2011-09-27 AU AU2011307731A patent/AU2011307731B2/en not_active Ceased
- 2011-09-27 WO PCT/CN2011/080220 patent/WO2012041218A1/zh active Application Filing
- 2011-09-27 EP EP11828114.6A patent/EP2623511B1/en active Active
- 2011-09-27 CA CA2813330A patent/CA2813330A1/en not_active Abandoned
- 2011-09-27 JP JP2013530549A patent/JP6000254B2/ja active Active
- 2011-09-27 RU RU2013118532/04A patent/RU2535489C1/ru not_active IP Right Cessation
- 2011-09-27 ES ES11828114.6T patent/ES2581562T3/es active Active
- 2011-09-27 US US13/877,427 patent/US8927690B2/en active Active
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4874843A (en) * | 1987-12-03 | 1989-10-17 | Eli Lilly And Company | Chromatographic purification process |
EP0431350B1 (en) | 1989-11-13 | 1995-07-26 | Fujisawa Pharmaceutical Co., Ltd. | New polypeptide compound and a process for preparation thereof |
US5376634A (en) | 1990-06-18 | 1994-12-27 | Fujisawa Pharmaceutical Co., Ltd. | Polypeptide compound and a process for preparation thereof |
CN1040541C (zh) | 1990-06-18 | 1998-11-04 | 藤泽药品工业株式会社 | 新型多肽化合物的制备方法 |
EP0486011A2 (en) * | 1990-11-16 | 1992-05-20 | Fujisawa Pharmaceutical Co., Ltd. | Pharmaceutical composition against Pneumocystis carinii |
EP1137663B1 (en) * | 1998-12-09 | 2006-08-30 | Eli Lilly And Company | Purification of echinocandin cyclopeptide compounds |
EP1197557A1 (en) * | 1999-07-02 | 2002-04-17 | Fujisawa Pharmaceutical Co., Ltd. | Gene encoding cyclic lipopeptide acylase and expression of the same |
US20100249371A1 (en) * | 2009-03-24 | 2010-09-30 | Cadila Healthcare Limited | Purification process for lipopeptides |
Non-Patent Citations (1)
Title |
---|
See also references of EP2623511A4 * |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8927690B2 (en) | 2010-09-29 | 2015-01-06 | Shanghai Techwell Biopharmaceutical Co., Ltd. | Process for purifying cyclolipopeptide compounds or the salts thereof |
WO2012143293A1 (en) * | 2011-04-20 | 2012-10-26 | Xellia Pharmaceuticals Aps | Method for purification of micafungin |
US9132163B2 (en) | 2011-04-20 | 2015-09-15 | Xellia Pharmaceuticals Aps | Method for purification of Micafungin |
EP2918324A1 (en) * | 2011-04-20 | 2015-09-16 | Xellia Pharmaceuticals ApS | Method for purification of micafungin |
AU2012244435B2 (en) * | 2011-04-20 | 2017-06-15 | Xellia Pharmaceuticals Aps | Method for purification of Micafungin |
US20150065417A1 (en) * | 2012-03-30 | 2015-03-05 | Shanghai Techwell Biophamaceutical Co., Ltd. | High purity cyclopeptide compound as well as preparation method and use thereof |
Also Published As
Publication number | Publication date |
---|---|
RU2535489C1 (ru) | 2014-12-10 |
RU2013118532A (ru) | 2014-11-10 |
US8927690B2 (en) | 2015-01-06 |
CA2813330A1 (en) | 2012-04-05 |
KR101514903B1 (ko) | 2015-04-23 |
JP2013538832A (ja) | 2013-10-17 |
KR20130059454A (ko) | 2013-06-05 |
AU2011307731B2 (en) | 2016-02-18 |
CN102432674B (zh) | 2014-01-22 |
US20130281665A1 (en) | 2013-10-24 |
EP2623511B1 (en) | 2016-04-06 |
JP6000254B2 (ja) | 2016-09-28 |
CN102432674A (zh) | 2012-05-02 |
ES2581562T3 (es) | 2016-09-06 |
EP2623511A4 (en) | 2014-04-16 |
EP2623511A1 (en) | 2013-08-07 |
AU2011307731A1 (en) | 2013-05-23 |
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