JPH05230062A - Method for concentrating carbapenem-based antibiotic substance - Google Patents
Method for concentrating carbapenem-based antibiotic substanceInfo
- Publication number
- JPH05230062A JPH05230062A JP4031125A JP3112592A JPH05230062A JP H05230062 A JPH05230062 A JP H05230062A JP 4031125 A JP4031125 A JP 4031125A JP 3112592 A JP3112592 A JP 3112592A JP H05230062 A JPH05230062 A JP H05230062A
- Authority
- JP
- Japan
- Prior art keywords
- carbapenem
- concentration
- reverse osmosis
- osmosis membrane
- concentrating
- 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.)
- Pending
Links
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A20/00—Water conservation; Efficient water supply; Efficient water use
- Y02A20/124—Water desalination
- Y02A20/131—Reverse-osmosis
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、熱に不安定なカルバペ
ネム系抗生物質の希薄水溶液をポリアミド系逆浸透膜で
処理し、カルバペネム系抗生物質の分解を防止しながら
効率よく濃縮することを目的とするカルバペネム系抗生
物質の濃縮方法に関する。BACKGROUND OF THE INVENTION The present invention aims to treat a dilute aqueous solution of a carbapenem antibiotic which is unstable to heat with a polyamide reverse osmosis membrane to efficiently concentrate it while preventing decomposition of the carbapenem antibiotic. And a method for concentrating carbapenem antibiotics.
【０００２】[0002]
【従来の技術】カルバペネム系抗生物質の安定性は概し
て濃度依存性が高く、従って合成化学的製造工程あるい
は精製工程では希薄水溶液で扱われる事が多い。従来よ
り、カルバペネム系抗生物質またはその誘導体の希薄水
溶液は、一般には蒸発機で熱を加えて溶媒を蒸発させる
濃縮法や水を一部凍結させて濃縮する凍結濃縮法で濃縮
されている。さらに近年、透過膜を使った低温濃縮法が
各分野で試みられており、酢酸セルロ−ス系膜によるβ
−ラクタム系抗生物質の濃縮法（特公平４−９９４号）
知られているが、酢酸セルロ−ス系膜やポリアミド系膜
ではβ−ラクタム系抗生物質の濃縮時に膜が破れること
が知られている（特公平２−４６１９８号）。BACKGROUND OF THE INVENTION The stability of carbapenem antibiotics is generally highly concentration-dependent, and is therefore often handled in dilute aqueous solutions in synthetic chemical manufacturing processes or purification processes. Conventionally, a dilute aqueous solution of a carbapenem antibiotic or a derivative thereof is generally concentrated by a concentration method in which heat is applied by an evaporator to evaporate a solvent or a freeze concentration method in which water is partially frozen and concentrated. Furthermore, in recent years, low-temperature concentration methods using permeable membranes have been tried in various fields, and β-cells using cellulose acetate-based membranes have been tried.
-Lactam antibiotic concentration method (Japanese Patent Publication No. 4-994)
It is known that cellulose acetate-based membranes and polyamide-based membranes are broken when β-lactam antibiotics are concentrated (Japanese Patent Publication No. 2-46198).
【０００３】[0003]
【発明が解決しようとする課題】カルバペネム系抗生物
質には熱に不安定なものが多く、従ってこのものの希薄
水溶液を蒸発で濃縮する場合にはかなりの分解が避けら
れないし、多大なエネルギ−を要し経済的に極めて不利
であり、凍結濃縮法も処理に長時間を要するばかりでな
く多大のエネルギ−を要し、しかも濃縮収率が低く経済
的に極めて不利である。また酢酸セルロ−ス系膜による
濃縮法は酢酸セルロ−ス系膜の許容ｐＨ範囲は３〜８に
あり、アルカリ側での膜の洗浄が出来ない。一般に逆浸
透膜の使用を繰り返す際、あるいは、このものの保存
中、膜表面が分解物あるいは微生物等の有機物質により
汚染され、水の透過速度が低下することはたびたび経験
するところである。この透過能力を復元する手段の一方
法として、酸あるいはアルカリ水溶液による洗浄が効果
的である。本発明で使用するポリアミド系逆浸透膜の許
容ｐＨ範囲は２〜１１と広くアルカリ側での濃縮ができ
るばかりでなく膜の洗浄及び濃縮装置の無菌管理にアル
カリが使用できる。Many carbapenem antibiotics are unstable to heat. Therefore, when diluting a dilute aqueous solution of these antibiotics, considerable decomposition is inevitable and a large amount of energy is consumed. This is very economically disadvantageous, and the freeze concentration method not only requires a long time for treatment, but also requires a large amount of energy, and the concentration yield is low, which is extremely economically disadvantageous. In the concentration method using a cellulose acetate-based membrane, the allowable pH range of the cellulose acetate-based membrane is 3 to 8, and the membrane cannot be washed on the alkaline side. In general, when the reverse osmosis membrane is used repeatedly or during storage, the membrane surface is often contaminated with decomposed substances or organic substances such as microorganisms, and the water permeation rate is often reduced. Washing with an acid or alkali aqueous solution is effective as one method of restoring the permeation ability. The allowable pH range of the polyamide reverse osmosis membrane used in the present invention is as wide as 2 to 11 and not only concentration on the alkali side is possible, but also alkali can be used for washing the membrane and aseptic control of the concentration device.
【０００４】本発明者等は、ポリアミド系逆浸透膜を使
用することによってカルバペネム系抗生物質の希薄水溶
液を低温かつ短時間に濃縮でき、濃縮中の分解を防止す
るとともに高収率でしかも経済的な濃縮法を見出し、本
発明を完成した。The present inventors have been able to concentrate a dilute aqueous solution of a carbapenem antibiotic at low temperature and in a short time by using a polyamide reverse osmosis membrane, prevent decomposition during the concentration, and obtain a high yield and economically. The present invention has been completed by finding a different concentration method.
【０００５】[0005]
【課題を解決するための手段】本発明は、カルバペネム
系抗生物質の希薄水溶液をポリアミド系逆浸透膜により
濃縮することを特徴とするカルバペネム系抗生物質水溶
液の濃縮方法に関するものである。The present invention relates to a method for concentrating a carbapenem antibiotic aqueous solution, which comprises concentrating a dilute aqueous solution of a carbapenem antibiotic with a polyamide reverse osmosis membrane.
【０００６】本発明は次のようなカルバペネム系抗生物
質の濃縮法に使用される。The present invention is used in the following method for concentrating carbapenem antibiotics.
【０００７】[0007]
【化１】 [Chemical 1]
【０００８】式中、Ｒ1 は水素原子または低級アルキル
基を示し、Ｒ2 は置換基を有してもよいヘテロシクリル
基を示す。In the formula, R 1 represents a hydrogen atom or a lower alkyl group, and R 2 represents a heterocyclyl group which may have a substituent.
【０００９】Ｒ1 は好適には水素原子またはメチル基を
示し、Ｒ2 は好適には置換基を有してもよいピロリジニ
ル基またはジヒドロピラゾロトリアゾリウム基があげら
れ、更に好適には置換基を有するピロリジニル基であ
る。その好適な置換基は、例えばカルバモイル、モノも
しくはジアルキルカルバモイル、置換基を有してもよい
ピペラジニルカルボニル、ホモピペラジニルカルボニ
ル、ピペラジニオカルボニルもしくはホモピペラジニオ
カルボニルまたはホルムイミドイルもしくはアセトイミ
ドイル基があげられる。R 1 is preferably a hydrogen atom or a methyl group, and R 2 is preferably a pyrrolidinyl group which may have a substituent or a dihydropyrazolotriazolium group, more preferably a substituted group. It is a pyrrolidinyl group having a group. Suitable substituents are, for example, carbamoyl, mono- or dialkylcarbamoyl, optionally substituted piperazinylcarbonyl, homopiperazinylcarbonyl, piperaziniocarbonyl or homopiperaziniocarbonyl or formimidoyl or acetoyl. Examples thereof include imidoyl groups.
【００１０】発明に使用されるポリアミド系逆浸透膜と
しては例えば、フイルムテック社製ＦＴ−３０（ＮａＣ
ｌ阻止率、９６％以上）、ル−ズ型ポリアミド系逆浸透
膜としてはフイルムテック社製ＮＦ−４０（ＮａＣｌ阻
止率、４０〜５０％以上）、デサリネ−ション社製Ｇ−
１０（ＮａＣｌ阻止率、５０〜６０％）が上げられ、好
適にはル−ズ型ポリアミド系逆浸透膜である。The polyamide-based reverse osmosis membrane used in the invention is, for example, FT-30 (NaC manufactured by Filmtec Co., Ltd.).
l blocking rate, 96% or more), as a loose polyamide reverse osmosis membrane, NF-40 (NaCl blocking rate, 40 to 50% or more) manufactured by Filmtec Co., G-made by Desalination Co., Ltd.
10 (NaCl inhibition rate, 50 to 60%), and is preferably a loose polyamide reverse osmosis membrane.
【００１１】本発明の濃縮方法において得られるカルバ
ペネム系抗生物質の限界濃度（重量％）は主にその物質
の浸透圧とそれに抗して付加する外圧との差によって決
まるが通常は１０〜３０％であり、好適には１０〜２５
％である。The limiting concentration (% by weight) of the carbapenem antibiotic obtained by the concentration method of the present invention is determined mainly by the difference between the osmotic pressure of the substance and the external pressure applied against it, but usually 10 to 30%. And preferably 10 to 25
%.
【００１２】本発明において、付加する外圧は膜の耐圧
性から上限が決まるが通常は５０Kg／cm2 であり、好適
には４０Kg／cm2 以下である。In the present invention, the upper limit of the applied external pressure is determined by the pressure resistance of the membrane, but is usually 50 kg / cm 2 , and preferably 40 kg / cm 2 or less.
【００１３】[0013]
【発明の効果】本発明に使用されるポリアミド系逆浸透
膜としてはスパイラル型モジュ−ルであり、必要に応じ
てこれを並列に使えば有効面積を任意に増加することが
できる。処理量の増大に対しても対処でき、得られた濃
縮液を必要に応じて循環処理すれば濃縮する物質の浸透
圧から来る限界濃度まで更に濃縮することができる。The polyamide-based reverse osmosis membrane used in the present invention is a spiral type module, and the effective area can be arbitrarily increased by using it in parallel if necessary. It is possible to cope with an increase in the amount to be treated, and if the obtained concentrated liquid is circulated as necessary, it is possible to further concentrate to the limit concentration coming from the osmotic pressure of the substance to be concentrated.
【００１４】本発明に使用されるポリアミド系逆浸透膜
のうちＮａＣｌ阻止率９０％以下のル−ズ型ポリアミド
系逆浸透膜は無機塩（ＮａＣｌ、ＫＣｌ等）及び親水性
低分子物質（例えば、メチルアルコ−ル、エチルアルコ
−ル、アセトニトリル、アセトン、テトラヒドロフラン
等の親水性低分子有機溶媒、或いは副生成物等）の透過
性に優れ、従って本発明の方法は、通常の製造方法によ
って得られるこれら不純物質を含む場合のカルバペネム
系抗生物質またはその誘導体の希薄溶液の濃縮方法とし
て極めて優れている。例えば、カルバペネム系抗生物質
の精製法として一般に使用されるクロマトグラフィ−法
の該溶出液には、数％から２０数％の親水性有機溶媒を
含有するが、本発明の方法は水の透過と同時にこれらの
溶媒も透過し、さらにこの際新たな水を添加しながら濃
縮すればこれらの溶媒もほぼ完全に除くことができる。Among the polyamide reverse osmosis membranes used in the present invention, the loose polyamide reverse osmosis membrane having a NaCl rejection rate of 90% or less is an inorganic salt (NaCl, KCl, etc.) and a hydrophilic low molecular weight substance (eg, It has excellent permeability to hydrophilic low molecular weight organic solvents such as methyl alcohol, ethyl alcohol, acetonitrile, acetone, tetrahydrofuran, etc., or by-products, and thus the method of the present invention can be obtained by a conventional production method. It is an excellent method for concentrating a dilute solution of a carbapenem antibiotic or its derivative when it contains impurities. For example, the eluate of a chromatographic method generally used as a method for purifying carbapenem antibiotics contains a few% to a few 20% of a hydrophilic organic solvent. These solvents also permeate, and at this time, these solvents can be almost completely removed by concentrating while adding new water.
【００１５】本発明により、熱に不安定なカルバペネム
系抗生物質が低温かつ短時間に高収率で濃縮でき、分解
を最小限にとどめることができる。According to the present invention, a thermolabile carbapenem antibiotic can be concentrated at a low temperature in a short time in a high yield, and decomposition can be minimized.
【００１６】以下に実施例をあげ具体的に説明する。Specific examples will be described below with reference to examples.
【００１７】[0017]
実施例１ （＋）−（５Ｒ，６Ｓ）−３−［（Ｓ）−１−（アセチ
ミドイルピロリジン−３−イル）チオ］−６−［（Ｒ）
−１−ヒドロキシエチル］−７−オキソ−１−アザビシ
クロ［３．２．０］ヘプト−２−エン−カルボン酸
（以下カルバペネムと称す）１．２８％、テトラヒドロ
フラン０．５％を含む水溶液４３０ｌを８℃、３５Kg／
cm2 の加圧下、５０ｌ／分の循環速度で逆浸透膜濃縮装
置（ミリポア社製装置、フイルムテック社製ポリアミド
系逆浸透膜ＦＴ−３０スパイラル４インチモジュ−ル長
さ１ｍ×３本、２１ｍ2 ）に送り込み循環濃縮を行っ
た。９５分後に濃縮液４２．３Kg、透過液約４００ｌが
得られた。濃縮収率は９８．７％、透過液中へのカルバ
ペネムのリ−ク量は０．５％であった。カルバペネムの
分解はほとんど認められなかった。Example 1 (+)-(5R, 6S) -3-[(S) -1- (acetimidoylpyrrolidin-3-yl) thio] -6-[(R)
-1-Hydroxyethyl] -7-oxo-1-azabicyclo [3.2.0] hept-2-ene-carboxylic acid
(Hereinafter referred to as carbapenem) 430 l of an aqueous solution containing 1.28% and tetrahydrofuran 0.5% at 8 ° C. and 35 kg /
Reverse osmosis membrane concentrator under pressure of cm 2 at a circulation rate of 50 l / min (Millipore Corporation apparatus, Filmtec polyamide reverse osmosis membrane FT-30 spiral 4 inch module length 1 m × 3, 21 m It was sent to 2 ) and concentrated by circulation. After 95 minutes, 42.3 kg of concentrated solution and about 400 l of permeated solution were obtained. The concentration yield was 98.7%, and the amount of carbapenem leak into the permeate was 0.5%. Almost no degradation of carbapenem was observed.
【００１８】実施例２ カルバペネム １．１８％、テトラヒドロフラン０．５
５％を含む水溶液５４０ｌを５℃、３０Kg／cm2 の加圧
下、５０ｌ／分の循環速度で逆浸透膜濃縮装置（ミリポ
ア社製装置、フイルムテック社製ル−ズ型ポリアミド系
逆浸透膜ＮＦ−４０スパイラル４インチモジュ−ル長さ
１ｍ×３本、２１ｍ2 ）に送り込み循環濃縮を行った。
６０分後に濃縮液４０．９Kg、透過液約５００ｌが得ら
れた。濃縮液中のカルバペネム含量は１５．１％、テト
ラヒドロフランの含量は０．８％であった。濃縮収率は
９７．０％、透過液中へのカルバペネムのリ−ク量は
２．１％であった。カルバペネムの分解はほとんど認め
られなかった。この濃縮液を更に同様な条件で濃縮した
ところ得られた濃縮液３０Kg中（濃度２０．１％）にテ
トラヒドロフランは検出されなかった。Example 2 Carbapenem 1.18%, tetrahydrofuran 0.5
A reverse osmosis membrane concentrator (a device manufactured by Millipore, a loose polyamide reverse osmosis membrane NF manufactured by Filmtec Co., Ltd.) at a circulation rate of 50 l / min under a pressure of 30 kg / cm 2 at 5 ° C. with an aqueous solution containing 5% of 540 l. A -40 spiral 4-inch module having a length of 1 m × 3, 21 m 2 ) was sent for circulation concentration.
After 60 minutes, 40.9 kg of concentrate and about 500 l of permeate were obtained. The carbapenem content in the concentrate was 15.1% and the tetrahydrofuran content was 0.8%. The concentration yield was 97.0% and the amount of carbapenem leak in the permeate was 2.1%. Almost no degradation of carbapenem was observed. Tetrahydrofuran was not detected in 30 kg of the concentrate obtained by further concentrating the concentrate under the same conditions (concentration: 20.1%).
【００１９】実施例３ カルバペネム １．３９％を含む水溶液４４０ｌを５
℃、３０Kg／cm2 の加圧下、５０ｌ／分の循環速度で逆
浸透膜濃縮装置（ミリポア社製装置、デサリネ−ション
社製ル−ズ型ポリアミド系逆浸透膜Ｇ−１０スパイラル
４インチモジュ−ル長さ１ｍ×３本、２１ｍ2 ）に送り
込み循環濃縮を行った。４０分後濃縮液３９．１Kg、透
過液約４００ｌが得られた。濃縮液中のカルバペネム濃
度は１５．１％、濃縮収率は９６．５％、透過液中への
カルバペネムのリ−ク量は２．９％であった。カルバペ
ネムの分解はほとんど認められなかった。Example 3 440 l of an aqueous solution containing 1.39% of carbapenem was added to 5 parts.
° C., under a pressure of 30 Kg / cm 2, the reverse osmosis membrane concentration apparatus circulation rate of 50 l / min (Millipore apparatus, Desarine - Deployment Corp. Le -'s type polyamide reverse osmosis membrane G-10 spiral 4 inches module - The solution was sent to a length of 1 m × 3, 21 m 2 ) for circulation concentration. After 40 minutes, 39.1 kg of concentrate and about 400 l of permeate were obtained. The concentration of carbapenem in the concentrate was 15.1%, the yield of concentration was 96.5%, and the leak amount of carbapenem in the permeate was 2.9%. Almost no degradation of carbapenem was observed.
─────────────────────────────────────────────────────
─────────────────────────────────────────────────── ───
【手続補正書】[Procedure amendment]
【提出日】平成４年３月４日[Submission date] March 4, 1992
【手続補正１】[Procedure Amendment 1]
【補正対象書類名】明細書[Document name to be amended] Statement
【補正対象項目名】０００２[Name of item to be corrected] 0002
【補正方法】変更[Correction method] Change
【補正内容】[Correction content]
【０００２】[0002]
【従来の技術】カルバペネム系抗生物質の安定性は概し
て濃度依存性が高く、従って合成化学的製造工程あるい
は精製工程では希薄水溶液で扱われる事が多い。従来よ
り、カルバペネム系抗生物質またはその誘導体の希薄水
溶液は、一般には蒸発機で熱を加えて溶媒を蒸発させる
濃縮法や水を一部凍結させて濃縮する凍結濃縮法で濃縮
されている。さらに近年、透過膜を使った低温濃縮法が
各分野で試みられており、酢酸セルロ−ス系膜によるβ
−ラクタム系抗生物質の濃縮法（特公平４−９９４号）
が知られているが、酢酸セルロ−ス系膜やポリアミド系
膜ではβ−ラクタム系抗生物質の濃縮時に膜が破れるこ
とが知られている（特公平２−４６１９８号）。BACKGROUND OF THE INVENTION The stability of carbapenem antibiotics is generally highly concentration-dependent, and is therefore often handled in dilute aqueous solutions in synthetic chemical manufacturing processes or purification processes. Conventionally, a dilute aqueous solution of a carbapenem antibiotic or a derivative thereof is generally concentrated by a concentration method in which heat is applied by an evaporator to evaporate a solvent or a freeze concentration method in which water is partially frozen and concentrated. Furthermore, in recent years, low-temperature concentration methods using permeable membranes have been tried in various fields, and β-cells using cellulose acetate-based membranes have been tried.
-Lactam antibiotic concentration method (Japanese Patent Publication No. 4-994)
It is known that cellulose acetate-based membranes and polyamide-based membranes are broken when β-lactam antibiotics are concentrated (Japanese Patent Publication No. 2-46198).
【手続補正２】[Procedure Amendment 2]
【補正対象書類名】明細書[Document name to be amended] Statement
【補正対象項目名】００１８[Correction target item name] 0018
【補正方法】変更[Correction method] Change
【補正内容】[Correction content]
【００１８】実施例２ カルバペネム １．１８％、テトラヒドロフラン０．５
５％を含む水溶液５４０ｌを５℃、３０Kg／cm2 の加圧
下、５０ｌ／分の循環速度で逆浸透膜濃縮装置（ミリポ
ア社製装置、フイルムテック社製ル−ズ型ポリアミド系
逆浸透膜ＮＦ−４０スパイラル４インチモジュ−ル長さ
１ｍ×３本、２１ｍ2 ）に送り込み循環濃縮を行った。
６０分後に濃縮液４０．９Kg、透過液約５００ｌが得ら
れた。濃縮液中のカルバペネム含量は１５．１％、テト
ラヒドロフランの含量は０．８％であった。濃縮収率は
９７．０％、透過液中へのカルバペネムのリ−ク量は
２．１％であった。カルバペネムの分解はほとんど認め
られなかった。この濃縮液を更に同様な条件で濃縮し
た。この際、水５００ｌを透過速度に見合った速度で添
加しながら濃縮したところ得られた濃縮液３０Kg中（濃
度２０．１％）にテトラヒドロフランは検出されなかっ
た。Example 2 Carbapenem 1.18%, tetrahydrofuran 0.5
A reverse osmosis membrane concentrator (a device made by Millipore, a loose-type polyamide reverse osmosis membrane NF made by Film Tech Co., Ltd.) at a circulation rate of 50 l / min under a pressure of 30 kg / cm 2 at 5 ° C. and 540 l of an aqueous solution containing 5%. A -40 spiral 4-inch module having a length of 1 m × 3, 21 m 2 ) was sent for circulation concentration.
After 60 minutes, 40.9 kg of concentrate and about 500 l of permeate were obtained. The carbapenem content in the concentrate was 15.1% and the tetrahydrofuran content was 0.8%. The concentration yield was 97.0% and the amount of carbapenem leak in the permeate was 2.1%. Almost no degradation of carbapenem was observed. This concentrated solution was further concentrated under the same conditions . At this time, add 500 l of water at a speed commensurate with the permeation speed.
Tetrahydrofuran was not detected in 30 kg of the concentrated liquid obtained by concentrating with addition (concentration: 20.1%).
Claims (1)
リアミド系逆浸透膜により濃縮することを特徴とするカ
ルバペネム系抗生物質水溶液の濃縮方法。1. A method for concentrating a carbapenem antibiotic aqueous solution, which comprises concentrating a dilute aqueous solution of a carbapenem antibiotic with a polyamide reverse osmosis membrane.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4031125A JPH05230062A (en) | 1992-02-19 | 1992-02-19 | Method for concentrating carbapenem-based antibiotic substance |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4031125A JPH05230062A (en) | 1992-02-19 | 1992-02-19 | Method for concentrating carbapenem-based antibiotic substance |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH05230062A true JPH05230062A (en) | 1993-09-07 |
Family
ID=12322706
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4031125A Pending JPH05230062A (en) | 1992-02-19 | 1992-02-19 | Method for concentrating carbapenem-based antibiotic substance |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH05230062A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103537192A (en) * | 2013-10-25 | 2014-01-29 | 上海珺领生化科技有限公司 | Membrane integration device for purifying and concentrating Ertapenem aqueous solution |
-
1992
- 1992-02-19 JP JP4031125A patent/JPH05230062A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103537192A (en) * | 2013-10-25 | 2014-01-29 | 上海珺领生化科技有限公司 | Membrane integration device for purifying and concentrating Ertapenem aqueous solution |
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