CN104644640A - Preparation method of cefoperazone sodium and sulbactam sodium powder injection for injection - Google Patents
Preparation method of cefoperazone sodium and sulbactam sodium powder injection for injection Download PDFInfo
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Abstract
The invention discloses a preparation method of a cefoperazone sodium and sulbactam sodium powder injection for injection. A recovered solvent is prepared by a stereo mass transfer tower plate technology, and is directly applied to production of cefoperazone sodium and sulbactam sodium products; the quality indexes such as color grade, clarity and purity of the obtained cefoperazone sodium and sulbactam sodium powder injection product for injection are greatly improved; the cefoperazone sodium and sulbactam sodium powder injection is high in quality stability and few in impurity; and the preparation method is low in production cost and simple in process.
Description
Technical field
This product relates to a kind of cefoperazone sodium and sulbactam sodium for injection powder injection formulation preparation method, belongs to medical art.
Background technology
The broad spectrum antibiotic that cefoperazone sodium in injection/sulbactam sodium is made up of cefoperazone sodium (third-generation cephalosporin) and the beta-lactam enzyme inhibitor sulbactam sodium with part antibacterial activity, to Grain-positive) bacterium, negative bacterium and part anaerobe have antagonism, especially obvious to gram negative bacteria effect, also there is stronger antagonism to Pseudomonas aeruginosa.Clinical practice is extensive, is mainly used in the diseases such as the respiratory tract infection for the treatment of caused by sensitive organism, urinary tract infection, septicemia and burn infection.
Cefoperazone sodium is third generation cephalosporin, and molecular weight is 667.66, and structural formula is as follows:
Its chemical name is (6R, 7R)-3-[[(1-methyl isophthalic acid H-tetrazolium-5-base) sulfur] methyl]-7-[(R)-2-(4-ethyl-2,3-dioxo-1-piperazine carbon acylamino)-2-p-hydroxybenzene-acetylamino]-8-oxo-5-thia-1-azabicyclo [4.2.0] oct-2-ene-2-formic acid sodium salt.
Cefoperazone sodium can disturb the synthesis of bacteria cell wall, makes newborn cell wall produce defect and bacteriolyze occurs.This effect realizes by acting on penicillin-binding protein (PBP) on cell wall.
First this achievement in research is developed compound preparation " sulperazone " by Pfizer, and takes the lead in going on the market in 1986 in Japan.Subsequently, then enter the multinational markets such as the U.S., Korea S, Turkey.
Sulbactam sodium, separately application is infected effectively to gonococcus and meningococcal surrounding, many and cefoperazone or ampicillin drug combination.Yuan Yan company is Pfizer Inc., within 1985, first in Britain's listing, within 1991, in France's listing, goes on the market in states such as European Union member countries and Australia such as Germany, Greece, Denmark at present.Its structural formula is as follows:
Its chemical name is (2S, 5R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo [3.2.0] heptane-2-carboxylic acid sodium-4,4-dioxide.
Cefoperazone sodium sulbactam sodium is a compound formulation, sulbactam is that wide spectrum enzyme inhibitor has more weak antibacterial activity simultaneously, to the beta-lactamase that S. aureus L-forms and most negative bacillus produce, there is powerful irreversible inhibitory action, but the beta-lactam kinase inactive to some negative bacillus Chromosome-encoded.
Because cefoperazone sodium and sulbactam sodium are lactam analog compound, cefoperazone sodium is weak acid strong alkali salt, and in chemical constitution, parent nucleus contains unstable beta-lactam nucleus, and effect falls in facile hydrolysis; Depositing in process, also because to thermally labile, and degraded and polyreaction usually occur, thus cause active constituents of medicine content to reduce, impurity raises.But as Tri-Biocin, clinical in intravenous drip administration, its quality criteria requirements is higher, and wherein determination of related substances is a main project.For cefoperazone sodium and sulbactam sodium for injection, be the compound preparation become according to certain proportions with sulbactam sodium by cefoperazone sodium, impurity introduces primarily of cefoperazone sodium and sulbactam sodium raw material or degraded produces.Therefore, start with from crude drug cefoperazone sodium and sulbactam sodium itself, improve the stability of himself, reduction degraded and polyreaction generation etc. and play a part very important to the quality, reduction impurity content etc. that improve cefoperazone sodium and sulbactam sodium for injection.
The packed tower that the existing solvent recovery technology of pharmaceutical industries adopts, there is mass-transfer efficiency low, operational stability is poor, and the solvent content of recovery is on the low side, and impurity is high, and then cannot directly apply to product regenerative ratio, or directly the rear product purity of producing of application is low, impurity is high.The solvent of usual recovery needs process further, thus increases production cost, improves technology difficulty.
Summary of the invention
For solving the above-mentioned defect of prior art, the object of the invention is to provide a kind of direct cefoperazone sodium and sulbactam sodium for injection injectable powder preparation method using the solvent reclaimed to produce, in color level, and clarity, the quality index such as purity improve a lot, and quality stability is high, impurity is few; Preparation method production cost is low, and technique is simple.
For achieving the above object, this invention takes following technical scheme: a kind of preparation method of cefoperazone sodium and sulbactam sodium for injection injectable powder, comprises the following steps:
(1) in dissolving tank, cefoperazone acid, purified water, solvent and salt forming agent is added, stir molten clear after be filtered in crystallizer, temperature control 15 ~ 20 DEG C, add solvent and carry out crystallization, 0 ~ 5 DEG C of growing the grain, filter, the wet-milling filtered is transferred in exsiccator, vacuum meter pressure-controlled is at≤-0.098MPa, and cold-draw 1.5 hours, is warming up to 45 ~ 50 DEG C of vacuum dryings and obtains cefoperazone sodium finished product;
(2) in dissolving tank, sulbactam, salt forming agent, solvent is added, temperature control 40 DEG C stir molten clear after be filtered in crystallizer, temperature control 40 DEG C, add solvent and carry out crystallization, 0 ~ 5 DEG C of growing the grain, filter, the wet-milling filtered is transferred in exsiccator, vacuum meter pressure-controlled is at≤-0.098MPa, and cold-draw 1 hour, is warming up to 45 ~ 50 DEG C of vacuum dryings and obtains sulbactam sodium finished product;
(3) sulbactam sodium of the cefoperazone sodium of step (1) and step (2) is sent between the subpackage of B level, under A level laminar flow, adopt screw filling machine to be divided in sterile vial by former medicine according to different size, the humiture that controls environment is 20 ~ 24 DEG C, and humidity is less than 40%.
Preferably, described solvent obtains for preparing recovery by three-dimensional column plate technology.
Preferably, described solvent is acetone, ethanol, isopropyl alcohol, one or more mixing in methanol.
Preferably, described in step (1), solvent is acetone, and described cefoperazone acid and described acetone weight ratio are 1:10 ~ 20; When tower top temperature is stabilized in 54.0-56.0 DEG C, sampling detects content of acetone in overhead reflux condensed fluid, and when acetone purity >=99.0%, moisture≤0.5%, opens extraction valve, slowly regulates extraction flow, until reflux ratio R=3-4, uses receiving tank extraction.
Preferably, described in step (2), solvent is ethanol, and described sulbactam and described ethanol weight ratio are 1:10 ~ 20; As solid mass-transferring column overhead temperatures < 85 DEG C, survey solvent content from the sampling of return duct sample tap, when content >=92.0%, then open extraction valve, controlling reflux ratio is 1.5 ~ 2, uses receiving tank extraction.
Preferably, described salt forming agent is one or more mixing in sodium bicarbonate, sodium carbonate, sodium acetate, Sodium isooctanoate..
Preferably, described in step (1), salt forming agent is sodium bicarbonate, and described cefoperazone acid and described sodium bicarbonate weight ratio are 4 ~ 6:1.
Preferably, described in step (2), salt forming agent is sodium acetate, and described cefoperazone acid and described sodium bicarbonate weight ratio are 1 ~ 2:1.
Preferably, mix after cefoperazone sodium described in step (3) and described sulbactam sodium aseptic mistake 40 ~ 80 eye mesh screen.
Preferably, cefoperazone sodium described in step (3) and described sulbactam sodium mass ratio are 1 ~ 2:1.
The solvent be recovered to is prepared with combined trapezoid spray tray new technique, it is lower to there is color level in quality, purity is high comparatively, directly apply among cefoperazone sodium sulbactam sodium production, the cefoperazone sodium and sulbactam sodium for injection powder pin product obtained, quality in color level, clarity, the quality index such as purity improve a lot, and wherein cefoperazone sodium and sulbactam sodium for injection quality stability are also greatly improved.
Embodiment 1 (adopting conventional art to reclaim solvent)
(1) preparation of cefoperazone sodium: add 200kg cefoperazone acid in dissolving tank, 200L purified water, the conventional art of 400L reclaims acetone, adds sodium bicarbonate 30kg, temperature control 15 DEG C, stir molten clear after, be filtered in crystallizer, temperature control 18 DEG C, continue to add conventional art recovery acetone 3600L and carry out crystallization, 0 ~ 5 DEG C of growing the grain, filter, 45 DEG C of vacuum dryings obtain cefoperazone sodium finished product.
(2) preparation of sulbactam sodium: add conventional art and reclaim ethanol 800L in dissolving tank, 200kg sulbactam, 200kg sodium acetate, 500L conventional art reclaims ethanol, after temperature control 40 DEG C stirs molten clear filtration, under temperature control 40 DEG C of conditions, add conventional art recovery ethanol 1500L and carry out crystallization, 0 ~ 5 DEG C of growing the grain, filtration washing, 45 DEG C of dryings obtain sulbactam sodium.
(3) the mixed powder preparation of aseptic cefoperazone sodium sulbactam sodium: cefoperazone sodium and sulbactam sodium 200kg (weight ratio is 1:1) are switched through to move in mixed powder machine after aseptic mistake 40 ~ 80 eye mesh screen mix, incorporation time is 35 minutes, temperature between aseptic mixed powder controls at 22 DEG C, and the humid control between mixed powder is 46%.After mixing terminates under the protection of hundred grades of laminar flows, in subpackage and sterilizing Aluminum Bottle, roll aluminium lid and obtain cefoperazone sodium sulbactam sodium and mix powder.
(4) cefoperazone sodium and sulbactam sodium for injection mixes the preparation of powder: cillin bottle clean and through tunnel sterilization tank 330 DEG C, sterilization time 10min, send into after sterilizing between subpackage, cefoperazone sodium sulbactam sodium aseptic powder 5kg sends between the subpackage of B level after cleaning de-bag, under A level laminar flow, adopt screw filling machine to be divided in sterile vial by former medicine according to 1.0g/ bottle, the humiture that controls environment is 20 ~ 24 DEG C, and humidity is less than 40%.
(5) cefoperazone sodium and sulbactam sodium for injection detects.Wherein, Key Quality Indicator: No. 0.25, clarity, color level≤3#, cefoperazone impurity A 0.52%, other maximum list assorted 0.73%, always mixes 1.7%.
Embodiment 2 (adopting conventional art to reclaim solvent)
(1) preparation of cefoperazone sodium: add 400kg cefoperazone acid in dissolving tank, 400L purified water, the conventional art of 600L reclaims acetone, add sodium bicarbonate 70kg, stir molten clear after, be filtered in crystallizer, continue to add conventional art recovery acetone 5000L and carry out crystallization, growing the grain, filters, 40 ~ 50 DEG C of dry cefoperazone sodium finished products.
(2) preparation of sulbactam sodium: add conventional art and reclaim ethanol 800L in dissolving tank, 200kg sulbactam, 200kg sodium acetate, 500L conventional art reclaims ethanol, after stirring molten clear filtration, add conventional art recovery ethanol 1500L and carry out crystallization, filtration washing, 40 ~ 50 DEG C of dryings obtain sulbactam sodium.
(3) the mixed powder preparation of cefoperazone sodium and sulbactam sodium for injection: by cefoperazone sodium and sulbactam sodium according to a certain percentage (2:1) mixed powder even after, carry out the subpackage of different size (2.0g) at formulating plant production line, obtain cefoperazone sodium and sulbactam sodium for injection.
(4) cefoperazone sodium and sulbactam sodium for injection detects.Wherein, Key Quality Indicator: No. 0.25, clarity, color level≤4#, cefoperazone impurity A 0.58%, other maximum list assorted 0.70%, always mixes 1.8%.
Comparative example 1 (adopting the solvent that this invention technology reclaims)
(1) preparation of cefoperazone sodium: add 200kg cefoperazone acid in dissolving tank, 160L purified water, this invention technology of 300L reclaims acetone, add sodium bicarbonate 26kg, stir molten clear after, be filtered in crystallizer, continue to add this invention technology recovery acetone 3500L and carry out crystallization, growing the grain, filters, dry cefoperazone sodium finished product.
(2) preparation of sulbactam sodium: add this invention technology and reclaim ethanol 800L in dissolving tank, 200kg sulbactam, 200kg sodium acetate, this invention technology of 450L reclaims ethanol, after stirring molten clear filtration, this is invented and carries out crystallization, filtration washing into new technique recovery ethanol 1500L, drying, obtains sulbactam sodium.
(3) preparation of cefoperazone sodium and sulbactam sodium for injection: by cefoperazone sodium and sulbactam sodium according to a certain percentage (1:1) mixed powder evenly after, carry out the subpackage of different size (1.0g) at formulating plant production line, obtain cefoperazone sodium and sulbactam sodium for injection.
(4) cefoperazone sodium and sulbactam sodium for injection detects.Wherein, No. 0.25, Key Quality Indicator: clarity <, color level≤2#, cefoperazone impurity A 0.20%, other maximum list assorted 0.50%, always mixes 1.4%.
Comparative example 2 (adopting this invention technology to reclaim solvent)
(1) preparation of cefoperazone sodium: add 400kg cefoperazone acid in dissolving tank, 400L purified water, this invention technology of 600L reclaims acetone, add sodium bicarbonate 70kg, stir molten clear after, be filtered in crystallizer, continue to add this invention technology recovery acetone 5000L and carry out crystallization, growing the grain, filters, 40 ~ 50 DEG C of dry cefoperazone sodium finished products.
(2) preparation of sulbactam sodium: add this invention technology and reclaim ethanol 800L in dissolving tank, 200kg sulbactam, 200kg sodium acetate, this invention technology of 500L reclaims ethanol, after stirring molten clear filtration, add this invention technology recovery ethanol 1500L and carry out crystallization, filtration washing, 40 ~ 50 DEG C of dryings obtain sulbactam sodium.
(3) the mixed powder preparation of cefoperazone sodium and sulbactam sodium for injection: by cefoperazone sodium and sulbactam sodium according to a certain percentage (2:1) mixed powder even after, carry out the subpackage of different size (2.0g) at formulating plant production line, obtain cefoperazone sodium and sulbactam sodium for injection.
(4) cefoperazone sodium and sulbactam sodium for injection detects.Wherein, No. 0.25, Key Quality Indicator: clarity <, color level≤2#, cefoperazone impurity A 0.22%, other maximum list assorted 0.43%, always mixes 1.3%.
Compared with conventional art, the present invention: the cefoperazone sodium provided and the pharmaceutical composition of sulbactam sodium are in color level, and clarity, related substance is significantly improved, product stability is better, and impurity content obviously reduces.
The quality versus's situation after solvent (content comprises purity, color level, and clarity contrasts) is reclaimed in combined trapezoid spray tray New technical use to cefoperazone and series of products thereof:
Table 1 reclaims the quality versus of rear acetone:
Table 2 reclaims the quality versus of rear ethanol:
Conclusion: as can be seen from the above table, after reclaiming solvent in combined trapezoid spray tray New technical use to cefoperazone sodium sulbactam sodium product, reclaim acetone and ethanol at moisture, color level, the quality index such as purity are significantly improved.
By above-described embodiment and comparative example simulation listing packaging, temperature 40 DEG C, place 6 months under relative humidity 75% condition, respectively at the 1st, 2,3, sampling in June, investigate appearance character, color level, the projects such as clarity, visible foreign matters, particulate matter, related substance, and with 0 day results contrast.
Result of the test is shown in Table 3:
As can be seen from above-mentioned accelerated test result, the cefoperazone sodium and sulbactam sodium for injection aseptic powder injection adopting the present invention to obtain is investigated through accelerated test for 6 months, and significant change does not occur indices, and traditional handicraft then there occurs significant change.The stability of cefoperazone sodium sulbactam sodium aseptic powder injection is higher than prior art.
Also carried out identical experiment to cefoperazone sodium and sulbactam sodium for injection aseptic powder injection prepared by other preparation specifications of the present invention, the result of the test of the result obtained and comparative example 1 and comparative example 2 is similar, but length limit, and the present invention will not enumerate.
More than describe preferred embodiment of the present invention in detail.Should be appreciated that those of ordinary skill in the art just design according to the present invention can make many modifications and variations without the need to creative work.Therefore, all technical staff in the art, all should by the determined protection domain of claims under this invention's idea on the basis of existing technology by the available technical scheme of logical analysis, reasoning, or a limited experiment.
Claims (10)
1. a preparation method for cefoperazone sodium and sulbactam sodium for injection injectable powder, is characterized in that, comprises the following steps:
(1) in dissolving tank, cefoperazone acid, purified water, solvent and salt forming agent is added, stir molten clear after be filtered in crystallizer, temperature control 15 ~ 20 DEG C, add solvent and carry out crystallization, 0 ~ 5 DEG C of growing the grain, filter, the wet-milling filtered is transferred in exsiccator, vacuum meter pressure-controlled is at≤-0.098MPa, and cold-draw 1.5 hours, is warming up to 45 ~ 50 DEG C of vacuum dryings and obtains cefoperazone sodium finished product;
(2) in dissolving tank, sulbactam, salt forming agent, solvent is added, temperature control 40 DEG C stir molten clear after be filtered in crystallizer, temperature control 40 DEG C, add solvent and carry out crystallization, 0 ~ 5 DEG C of growing the grain, filter, the wet-milling filtered is transferred in exsiccator, vacuum meter pressure-controlled is at≤-0.098MPa, and cold-draw 1 hour, is warming up to 45 ~ 50 DEG C of vacuum dryings and obtains sulbactam sodium finished product;
(3) sulbactam sodium of the cefoperazone sodium of step (1) and step (2) is sent between the subpackage of B level, under A level laminar flow, adopt screw filling machine to be divided in sterile vial by former medicine according to different size, the humiture that controls environment is 20 ~ 24 DEG C, and humidity is less than 40%.
2. the preparation method of cefoperazone sodium and sulbactam sodium for injection injectable powder according to claim 1, is characterized in that, described solvent obtains for preparing recovery by three-dimensional column plate technology.
3. the preparation method of cefoperazone sodium and sulbactam sodium for injection injectable powder according to claim 1, is characterized in that, described solvent is acetone, ethanol, isopropyl alcohol, one or more mixing in methanol.
4. the preparation method of cefoperazone sodium and sulbactam sodium for injection injectable powder according to claim 1, is characterized in that, described in step (1), solvent is acetone, and described cefoperazone acid and described acetone weight ratio are 1:10 ~ 20.
5. the preparation method of cefoperazone sodium and sulbactam sodium for injection injectable powder according to claim 1, is characterized in that, described in step (2), solvent is ethanol, and described sulbactam and described ethanol weight ratio are 1:10 ~ 20.
6. the preparation method of cefoperazone sodium and sulbactam sodium for injection injectable powder according to claim 1, is characterized in that, described salt forming agent is one or more mixing in sodium bicarbonate, sodium carbonate, sodium acetate, Sodium isooctanoate..
7. the preparation method of cefoperazone sodium and sulbactam sodium for injection injectable powder according to claim 1, is characterized in that, described in step (1), salt forming agent is sodium bicarbonate, and described cefoperazone acid and described sodium bicarbonate weight ratio are 4 ~ 6:1.
8. the preparation method of cefoperazone sodium and sulbactam sodium for injection injectable powder according to claim 1, is characterized in that, described in step (2), salt forming agent is sodium acetate, and described cefoperazone acid and described sodium bicarbonate weight ratio are 1 ~ 2:1.
9. the preparation method of cefoperazone sodium and sulbactam sodium for injection injectable powder according to claim 1, is characterized in that, mixes after cefoperazone sodium described in described step (3) and described sulbactam sodium aseptic mistake 40 ~ 80 eye mesh screen.
10. the preparation method of cefoperazone sodium and sulbactam sodium for injection injectable powder according to claim 1, is characterized in that, cefoperazone sodium described in described step (3) and described sulbactam sodium mass ratio are 1 ~ 2:1.
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Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
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CN104876946A (en) * | 2015-04-30 | 2015-09-02 | 王雪雁 | Sulbactam compound for treating infectious diseases, and preparation method therefor |
CN105440057A (en) * | 2015-11-25 | 2016-03-30 | 华北制药河北华民药业有限责任公司 | Method for preparing cefoperazone sodium |
CN106309448A (en) * | 2016-08-24 | 2017-01-11 | 南昌立健药业有限公司 | Novel cefoperazone sodium and sulbactam sodium pharmaceutical composition for injection |
CN106389358A (en) * | 2016-11-09 | 2017-02-15 | 重庆福安药业集团庆余堂制药有限公司 | Injection cefoperazone sodium and sulbactam sodium pharmaceutical composition for reducing allergic reaction |
CN106432273A (en) * | 2016-09-07 | 2017-02-22 | 陕西顿斯制药有限公司 | Cefoperazone sodium compound prepared by using fluid mechanics principle and preparation comprising cefoperazone sodium compound |
CN106432277A (en) * | 2016-09-21 | 2017-02-22 | 陕西顿斯制药有限公司 | Cefoperazone sodium compound and sulbactam sodium compound prepared with strong-field coupling crystallization technology as well as prepared composition |
CN106565749A (en) * | 2016-09-30 | 2017-04-19 | 华北制药河北华民药业有限责任公司 | Method for improving quality of cemandil sodium by using three-dimensional column plate to purify solvent |
CN107080750A (en) * | 2017-04-26 | 2017-08-22 | 四川制药制剂有限公司 | Cefoperazone sodium and sulbactam sodium for injection preparation technology |
CN108690050A (en) * | 2018-06-14 | 2018-10-23 | 华北制药河北华民药业有限责任公司 | A kind of purification process of sulbactam |
CN109293680A (en) * | 2018-09-26 | 2019-02-01 | 华北制药河北华民药业有限责任公司 | A kind of preparation method of cefoperazone acid |
CN110893232A (en) * | 2019-09-25 | 2020-03-20 | 上海欣峰制药有限公司 | Cefoperazone sodium and sulbactam sodium powder injection for injection and preparation method thereof |
CN112279868A (en) * | 2020-09-24 | 2021-01-29 | 华北制药河北华民药业有限责任公司 | Method for purifying cefoperazone sodium |
CN112279867A (en) * | 2020-09-24 | 2021-01-29 | 华北制药河北华民药业有限责任公司 | Preparation method of cefoperazone sodium |
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CN104876946A (en) * | 2015-04-30 | 2015-09-02 | 王雪雁 | Sulbactam compound for treating infectious diseases, and preparation method therefor |
CN105440057A (en) * | 2015-11-25 | 2016-03-30 | 华北制药河北华民药业有限责任公司 | Method for preparing cefoperazone sodium |
CN105440057B (en) * | 2015-11-25 | 2017-10-17 | 华北制药河北华民药业有限责任公司 | A kind of method for preparing cefoperazone sodium |
CN106309448A (en) * | 2016-08-24 | 2017-01-11 | 南昌立健药业有限公司 | Novel cefoperazone sodium and sulbactam sodium pharmaceutical composition for injection |
CN106432273A (en) * | 2016-09-07 | 2017-02-22 | 陕西顿斯制药有限公司 | Cefoperazone sodium compound prepared by using fluid mechanics principle and preparation comprising cefoperazone sodium compound |
CN106432277A (en) * | 2016-09-21 | 2017-02-22 | 陕西顿斯制药有限公司 | Cefoperazone sodium compound and sulbactam sodium compound prepared with strong-field coupling crystallization technology as well as prepared composition |
CN106565749A (en) * | 2016-09-30 | 2017-04-19 | 华北制药河北华民药业有限责任公司 | Method for improving quality of cemandil sodium by using three-dimensional column plate to purify solvent |
CN106389358A (en) * | 2016-11-09 | 2017-02-15 | 重庆福安药业集团庆余堂制药有限公司 | Injection cefoperazone sodium and sulbactam sodium pharmaceutical composition for reducing allergic reaction |
CN107080750A (en) * | 2017-04-26 | 2017-08-22 | 四川制药制剂有限公司 | Cefoperazone sodium and sulbactam sodium for injection preparation technology |
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CN108690050B (en) * | 2018-06-14 | 2019-11-08 | 华北制药河北华民药业有限责任公司 | A kind of purification process of sulbactam |
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CN109293680B (en) * | 2018-09-26 | 2020-06-16 | 华北制药河北华民药业有限责任公司 | Preparation method of cefoperazone acid |
CN110893232A (en) * | 2019-09-25 | 2020-03-20 | 上海欣峰制药有限公司 | Cefoperazone sodium and sulbactam sodium powder injection for injection and preparation method thereof |
CN112279868A (en) * | 2020-09-24 | 2021-01-29 | 华北制药河北华民药业有限责任公司 | Method for purifying cefoperazone sodium |
CN112279867A (en) * | 2020-09-24 | 2021-01-29 | 华北制药河北华民药业有限责任公司 | Preparation method of cefoperazone sodium |
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