CN102295653A - One-step recovery and preparation method of cefuroxime sodium - Google Patents
One-step recovery and preparation method of cefuroxime sodium Download PDFInfo
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Abstract
The invention relates to a one-step recovery and preparation method of cefuroxime sodium. The method comprises the following steps: dispersing cefuroxime sodium in a water-containing or water-free mixed solvent of alcohol and ketone, and adding hydrochloric acid or sulfur acid at the temperature of 0-50 DGE C to react for 0.5-3 hours, so that cefuroxime sodium is gradually converted into cefuroxime acid to be dissolved in a reaction system and simultaneously, a generated byproduct sodium chloride or sodium sulfate is not dissolved in the reaction system; adding activated carbon for decoloring, and filtering to remove the byproduct and the activated carbon to obtain a cefuroxime acid solution; and mixing the obtained cefuroxime acid solution with a solution of a water-containing or water-free organic solvent of sodium lactate or sodium iso-octoate so as to separate out cefuroxime sodium crystals. According to the invention, the recovery and preparation of cefuroxime sodium are carried out in one step in no need of separating out and drying cefuroxime acid, thus the damage to cefuroxime acid is reduced; and in the recovery and preparation process, the system has low water content, which has a good protection effect on unstable cefuroxime sodium.
Description
Technical field
The invention belongs to medical technical field, relate to a kind of recovery preparation method of cynnematin, more specifically, the single stage method that relates to Cefuroxime sodium reclaims the preparation method.
Background technology
Cefuroxime sodium is a kind of semi-synthetic second generation cephalosporin, and golden Portugal bacterium, suis, meningococcus, hemophilus influenza, klebsiella bacillus, intestinal bacteria, Proteus mirabilis, salmonella, shigella etc. are had the height anti-microbial effect.This product can be to anti-beta-lactamase, and is effective to penicillin-fast golden Portugal bacterium.The clinical infection that is mainly used in respiratory tract infection, pyelonephritis, urinary tract infections and bone due to the sensitive organism, joint, ear,nose ﹠ throat, soft tissue etc.This product has capacity to enter in the cerebrospinal fluid when the meninx inflammation, and is evident in efficacy to the meningitis due to the meningococcus.Activity and first-generation cephalo to gram positive organism (comprising penicillin resistant gold grape) are similar; Effect to gram-negative bacteria is strong than first-generation cephalo.
The chemical name of Cefuroxime sodium be (6R, 7R)-7-[2-furyl (methoxyimino) kharophen]-3-carbamyl oxygen methyl-8-oxo-5-thia-1-azabicyclic [4.2.0] oct-2-ene-2-sodium formiate, molecular formula is C
16H
15N
4NaO
8S, molecular weight are 446.36.Its chemical structural formula is represented with following formula I:
There is the problem of poor stability in Cefuroxime sodium always, is mainly reflected in product colour and changes very fast.In the Cefuroxime sodium suitability for industrialized production, because substandard product appears in the influence of technology or production environment sometimes in the production, add the Cefuroxime sodium poor stability, in the Cefuroxime sodium storage process, product colour rises to defective gradually in field of commercial circulation.Because the defective Cefuroxime sodium that occurs in production process or the storage process need reclaim, and the recovery of Cefuroxime sodium is a difficult point problem.
General Cefuroxime sodium has two kinds of ways of recycling, method one is to adopt underproof Cefuroxime sodium is dissolved in water, be translated into cefuroxime acid in an amount of acid of adding, behind the filtering drying, prepare Cefuroxime sodium with suitable Cefuroxime sodium preparation technology again; Method two adopts Cefuroxime sodium to be dissolved in the water, and behind decolorizing with activated carbon, adds certain organic solvent and separates out Cefuroxime sodium.
The common defects of these two kinds of methods is:
1. in method one, adopt two-step approach to reclaim Cefuroxime sodium, after Cefuroxime sodium changes into cefuroxime acid, often need to dry the back and use.If do not dry, the one, be not suitable for depositing, the wet product colour-change of cefuroxime acid is very fast; The 2nd, the use that is not suitable for feeding intake because contain a large amount of water in the wet product of cefuroxime acid, is given in the system for preparing Cefuroxime sodium and is brought a large amount of water into, influences the preparation of Cefuroxime sodium.So the wet product of cefuroxime acid generally need be dried processing, and in the oven dry treating processes time long, general 100 kilograms of cefuroxime acids that feed intake need to reach oven dry in 5～10 hours under 30～50 degree conditions, like this in drying course, cefuroxime acid is in hot and humid state, can cause cefuroxime acid color and impurity all to rise, the Cefuroxime sodium quality of recovery is not good.
2. method two seems simple, there are not to add in the method one acidic substance and cefuroxime acid drying course yet, but the underproof Cefuroxime sodium Cefuroxime sodium particle that recrystallization is often separated out in water and organic solvent is thin, and impurity is not easy to remove, product is not easy oven dry, and quality product and yield all are not so good as people's will.
3. method one and method two all use relatively large water to carry out the dissolving of defective Cefuroxime sodium, and in water, the colour-change of Cefuroxime sodium is fast especially, as " in the Chinese pharmacopoeia 2005 editions, the color of Cefuroxime sodium need be dissolved measurement in 0.05mol/L Calcium Disodium Versenate solution, all be to measure with water dissolution and measure color as cynnematins such as ceftriaxone sodium, T-1551s.Illustrate that Cefuroxime sodium colour-change in water is very fast, just can observe the intensification gradually of cephalofruxin sodium water solution color near measuring this short several minutes of color.And the method for above-mentioned two recovery all will use a large amount of water to carry out the dissolving of Cefuroxime sodium, so the quality of the Cefuroxime sodium that reclaims is often bad.If the dissolved time is spun out in the suitability for industrialized production, even the Cefuroxime sodium phenomenon also darker than the color of former Cefuroxime sodium after occurring reclaiming.
In order to overcome above-mentioned shortcoming, need seek the Cefuroxime sodium that is more suitable in suitability for industrialized production for this reason and reclaim the preparation method.
Summary of the invention
The purpose of this invention is to provide a kind of novel method that is more suitable for suitability for industrialized production, technology is simple, product purity is high and yield is high recovery Cefuroxime sodium.
For implementing purpose of the present invention, the technical scheme of employing is as follows:
Cefuroxime sodium is scattered in the mixed solvent of moisture or water-free alcohol and ketone, under 0～50 ℃ of temperature, add hydrochloric acid or sulfuric acid, reacted 0.5～3 hour, Cefuroxime sodium is gradually transformed into cefuroxime acid and is dissolved in the reaction system, and by product sodium-chlor of Sheng Chenging or sodium sulfate are insoluble in the reaction system simultaneously; Then add decolorizing with activated carbon, filter, filtering by product and activated carbon obtain the cephalofruxin acid solution; Resulting cephalofruxin acid solution mixes with the solution of the moisture or water-free organic solvent of Sodium.alpha.-hydroxypropionate or Sodium isooctanoate, and the cephalofruxin sodium crystal is separated out.
Single stage method at Cefuroxime sodium of the present invention reclaims among the preparation method,
The raw material feed ratio is in mol, and Cefuroxime sodium is 1: 0.8～1.7 with the ratio of acid, be preferably 1: 0.9～and 1.3, and most preferably be 1: 1.0～1.2;
The weight ratio of Cefuroxime sodium and activated carbon is 1: 0.01～0.2, be preferably 1: 0.03～and 0.15, and most preferably be 1: 0.05～0.1;
In the mixed solvent of described moisture or water-free alcohol and ketone, alcohol wherein is methyl alcohol, ethanol or Virahol, and ketone is acetone, and alcohol and the volume ratio of ketone be 1: 0.5～10, be preferably 1: 1～and 5, most preferably be 1: 1.5～3; The mixed solvent consumption of described moisture or water-free alcohol and ketone with this solvent and Cefuroxime sodium by volume/weight is 10～50L/1kg, is preferably 15～35L/1kg, and most preferably is 18～25L/1kg; The mixed solvent of moisture or water-free alcohol and ketone, wherein water and alcohol are 0.0～10: 100 (L/L) with the volume ratio of the mixed solvent of ketone, are preferably 1.0～8.0: 100 (L/L), and most preferably be 2.0～5.0: 100 (L/L).
Described hydrochloric acid or sulfuric acid, it is used for Cefuroxime sodium is converted into cefuroxime acid;
Described temperature of reaction is 0 ℃～50 ℃, and more preferably temperature range is 10 ℃～40 ℃.Reaction times, and different, the reaction times directly influenced the yield and the quality product of product with the kind of starting material, solvent, acid and consumption thereof, temperature of reaction.Reaction temperature is spent when hanging down, and reaction not exclusively makes product yield on the low side; When temperature of reaction is too high, be easy to generate side reaction, produce impurity, influence quality product and yield.
The solution of the moisture or water-free organic solvent of Sodium.alpha.-hydroxypropionate or Sodium isooctanoate, organic solvent wherein can adopt lower alcohol or lower ketones etc., and the mixed solvent of particular methanol, ethanol, Virahol, acetone or these solvents.Moisture or water-free consumption of organic solvent with this solvent and Sodium.alpha.-hydroxypropionate or Sodium isooctanoate by volume/weight is 2～25L/1kg, is preferably 5～15L/1kg, and most preferably is 6～10L/1kg; Moisture or water-free organic solvent, wherein water is 0.0～10.0: 100 (L/L) with the volume of organic solvent ratio, is preferably 2.0～8.0: 100 (L/L), and most preferably be 2.5～5.0: 100 (L/L).
In mol, cefuroxime acid is 1: 0.8～3.0 with the ratio of Sodium.alpha.-hydroxypropionate or Sodium isooctanoate, be preferably 1: 1.0～and 2.5, and most preferably be 1: 1.5～2.1.
The solution of resulting cephalofruxin acid solution with the moisture or water-free organic solvent of Sodium.alpha.-hydroxypropionate or Sodium isooctanoate is mixed, under 0～50 ℃ of temperature, stirred 0.5～5 hour, and the cephalofruxin sodium crystal is separated out; Filter then, wash, drying obtains Cefuroxime sodium.
The invention has the advantages that:
(1) adopt single stage method to carry out the recovery preparation of Cefuroxime sodium, do not need cefuroxime acid is separated and oven dry, minimizing is to the destruction of cefuroxime acid, crystallization, filtration washing, the drying time of cefuroxime acid have been omitted, improving recovery operation efficient, is a yield height, good product quality, the Cefuroxime sodium that is suitable for suitability for industrialized production reclaims the preparation method;
(2) content of water in system is low in the recovery preparation process, and unsettled Cefuroxime sodium is had good protective action;
(3) the present invention utilize cefuroxime acid, Cefuroxime sodium and by product sodium-chlor or sodium sulfate in same solvent system different solubility and separate.Change in the reaction system of cefuroxime acid at Cefuroxime sodium, the moisture or water-free alcohol that is adopted and the mixed solvent of ketone, the mixed solvent of this specified proportion, Cefuroxime sodium are not dissolve or the denier dissolved; By adding hydrochloric acid or sulfuric acid, Cefuroxime sodium is changed into cefuroxime acid, cefuroxime acid is a dissolved at this solvent system; Having generated by product sodium-chlor or sodium sulfate simultaneously is indissoluble at this solvent system, just the by product filtering can be guaranteed in the cephalofruxin acid solution after by product can not take filtration to by simple filtering like this.In the Cefuroxime sodium crystallisation process of back, can not bring unnecessary impurity into like this, guarantee the quality of product.When removing by product, do not need like this cefuroxime acid is separated and oven dry, minimizing is to the destruction of cefuroxime acid, crystallization, filtration washing, the drying time of cefuroxime acid have been omitted, improving recovery operation efficient, is a yield height, good product quality, the Cefuroxime sodium that is suitable for suitability for industrialized production reclaims the preparation method.
Embodiment
Further set forth technical scheme of the present invention below by specific embodiment, but the following examples should not be construed as limiting the scope of the invention.
Embodiment 1
(color and luster equals yellow No. 7 with the underproof Cefuroxime sodium of 10 grams, content 92%) add in 100ml 95% ethanol and the 200ml acetone, add hydrochloric acid 1.3ml (it is formulated to add water 0.65ml by 36% hydrochloric acid 0.65ml), 10～15 ℃ of insulation reaction 2 hours, Cefuroxime sodium is gradually transformed into cefuroxime acid and is dissolved in the reaction system; Add activated carbon 1 gram, stir decolouring after 15 minutes, filter, filtering activated carbon, filter cake 20ml washing with alcohol, merging filtrate with wash carbon liquid, obtain the cephalofruxin acid solution.
20～25 ℃, the Sodium.alpha.-hydroxypropionate and the 75ml alcoholic acid mixing solutions of 6 grams 60% are under agitation joined in the above-mentioned cephalofruxin acid solution, finish, continue to stir 1 hour, filter, collect and use the washing with alcohol crystal, this crystal promptly gets Cefuroxime sodium 9.2 grams, yield 92% 35～45 ℃ of following vacuum-dryings.The Cefuroxime sodium that obtains equals yellow No. 3 by the detection method detection color of " Chinese Pharmacopoeia 2005 editions " regulation, and content is 95.5%, meets " Chinese Pharmacopoeia 2005 editions " standard.
Embodiment 2
(color and luster equals yellow No. 8 with the underproof Cefuroxime sodium of 10 grams, content 91%) add in 300ml methyl alcohol and the 150ml acetone, add sulfuric acid 10ml (it is formulated to add 9ml water by 98% sulfuric acid of 1ml), 0～10 ℃ of insulation reaction 1 hour, Cefuroxime sodium is gradually transformed into cefuroxime acid and is dissolved in the reaction system, add activated carbon 2 grams, stir after 15 minutes, filter, use the 50ml methanol wash, merging filtrate and wash carbon liquid obtains the cephalofruxin acid solution.
0～15 ℃, the mixing solutions of 12.5 gram 60% Sodium.alpha.-hydroxypropionates and 120ml acetone is under agitation joined in the above-mentioned cephalofruxin acid solution, finish, continue to stir 4～5 hours, filter, collect and use the washing with acetone crystal, this crystal promptly gets Cefuroxime sodium 8.9 grams, yield 89% 35～45 ℃ of following vacuum-dryings.The Cefuroxime sodium that obtains detects color less than yellow No. 4 by the detection method of " Chinese Pharmacopoeia 2005 editions " regulation, and content is 95.2%, meets " Chinese Pharmacopoeia 2005 editions " standard.
Embodiment 3
(clarity of Cefuroxime sodium is greater than No. 2 turbidity standards with the underproof Cefuroxime sodium of 10 grams, content 91%) add in 80ml acetone and the 20ml Virahol, add hydrochloric acid 2.2ml (it is formulated to add water 1.1ml by 36% hydrochloric acid 1.1ml), 40～50 ℃ of insulation reaction 0.5 hour, Cefuroxime sodium is gradually transformed into cefuroxime acid and is dissolved in the reaction system, add activated carbon 0.1 gram, stir after 15 minutes, filter, use the 20ml washing with acetone, merging filtrate and wash carbon liquid obtains the cephalofruxin acid solution.
40～50 ℃, restraining Sodium isooctanoates and 16ml acetone and 1.6ml water mixed solution with 8 under agitation joins in the above-mentioned cephalofruxin acid solution, finish, continue to stir 1 hour, filter, collect and use the washing with acetone crystal, this crystal is 35～45 ℃ of following vacuum-dryings, promptly get Cefuroxime sodium 8.7 grams, yield 87%, the Cefuroxime sodium that obtains is that clarity is less than No. 1 turbidity standard by the detection method detection of " Chinese Pharmacopoeia 2005 editions " regulation, content is 95.4%, meets " Chinese Pharmacopoeia 2005 editions " standard.
Embodiment 4
With 10 gram content is that 85% underproof Cefuroxime sodium adds in 18ml 95% ethanol and the 180ml acetone, add hydrochloric acid 2.2ml (it is formulated to add water 1.65ml by 36% hydrochloric acid 0.55ml), 10～20 ℃ of insulation reaction 3 hours, Cefuroxime sodium is gradually transformed into cefuroxime acid and is dissolved in the reaction system, adds activated carbon 1.0 grams, stirs after 15 minutes, filter, use the 50ml washing with alcohol, merging filtrate and wash carbon liquid obtains the cephalofruxin acid solution.
20～30 ℃, the Sodium.alpha.-hydroxypropionate and the 68ml alcoholic acid mixing solutions of 3.4 grams 60% are under agitation joined in the above-mentioned cephalofruxin acid solution, finish, continue to stir 1 hour, filter, collect and use the washing with alcohol crystal, this crystal promptly gets Cefuroxime sodium 8.2 grams, yield 82% 35～45 ℃ of following vacuum-dryings.The Cefuroxime sodium that obtains detects to content is 93.1% by the detection method of " Chinese Pharmacopoeia 2005 editions " regulation, meets " Chinese Pharmacopoeia 2005 editions " standard.
Claims (8)
1. the single stage method of a Cefuroxime sodium reclaims the preparation method, it is characterized in that this method comprises:
Cefuroxime sodium is scattered in the mixed solvent of moisture or water-free alcohol and ketone, under 0～50 ℃ of temperature, add hydrochloric acid or sulfuric acid, reacted 0.5～3 hour, Cefuroxime sodium is gradually transformed into cefuroxime acid and is dissolved in the reaction system, and by product sodium-chlor of Sheng Chenging or sodium sulfate are insoluble in the reaction system simultaneously; Then add decolorizing with activated carbon, filter, filtering by product and activated carbon obtain the cephalofruxin acid solution; Resulting cephalofruxin acid solution mixes with the solution of the moisture or water-free organic solvent of Sodium.alpha.-hydroxypropionate or Sodium isooctanoate, and the cephalofruxin sodium crystal is separated out;
Wherein, in mol, Cefuroxime sodium is 1: 0.8～1.7 with the ratio of acid;
In the mixed solvent of described moisture or water-free alcohol and ketone, alcohol wherein is methyl alcohol, ethanol or Virahol, and ketone is acetone, and the volume ratio of alcohol and ketone is 1: 0.5～10; The mixed solvent consumption of described moisture or water-free alcohol and ketone with this solvent and Cefuroxime sodium by volume/weight is 10～50L/1kg; The mixed solvent of moisture or water-free alcohol and ketone, wherein water and alcohol are 0.0～10: 100 with the volume ratio of the mixed solvent of ketone;
The solution of the moisture or water-free organic solvent of Sodium.alpha.-hydroxypropionate or Sodium isooctanoate, organic solvent wherein are the mixed solvent of methyl alcohol, ethanol, Virahol, acetone or these solvents; Moisture or water-free consumption of organic solvent with this solvent and Sodium.alpha.-hydroxypropionate or Sodium isooctanoate by volume/weight is 2～25L/1kg; Moisture or water-free organic solvent, wherein water is 0.0～10.0: 100 with the volume of organic solvent ratio;
In mol, cefuroxime acid is 1: 0.8～3.0 with the ratio of Sodium.alpha.-hydroxypropionate or Sodium isooctanoate.
2. preparation method according to claim 1 is characterized in that, in mol, Cefuroxime sodium is 1: 0.9～1.3 with the ratio of acid, and be preferably 1: 1.0～1.2.
3. preparation method according to claim 1 and 2 is characterized in that the weight ratio of Cefuroxime sodium and activated carbon is 1: 0.01～0.2, be preferably 1: 0.03～and 0.15, and most preferably be 1: 0.05～0.1.
4. each described preparation method in requiring according to aforesaid right is characterized in that, in the mixed solvent of described moisture or water-free alcohol and ketone, alcohol wherein is methyl alcohol, ethanol or Virahol, ketone is acetone, and alcohol and the volume ratio of ketone be 1: 1～5, be preferably 1: 1.5～and 3; The mixed solvent consumption of described moisture or water-free alcohol and ketone with this solvent and Cefuroxime sodium by volume/weight is 15～35L/1kg, and is preferably 18～25L/1kg; The mixed solvent of moisture or water-free alcohol and ketone, wherein water and alcohol are 1.0～8.0: 100 with the volume ratio of the mixed solvent of ketone, and are preferably 2.0～5.0: 100.
5. each described preparation method in requiring according to aforesaid right is characterized in that the temperature of reaction that Cefuroxime sodium changes into cefuroxime acid is 10 ℃～40 ℃.
6. each described preparation method in requiring according to aforesaid right, it is characterized in that in mol, cefuroxime acid is 1: 1.0～2.5 with the ratio of Sodium.alpha.-hydroxypropionate or Sodium isooctanoate, and be preferably 1: 1.5～2.1.
7. each described preparation method in requiring according to aforesaid right, it is characterized in that, in the solution of the moisture or water-free organic solvent of described Sodium.alpha.-hydroxypropionate or Sodium isooctanoate, moisture or water-free consumption of organic solvent with this solvent and Sodium.alpha.-hydroxypropionate or Sodium isooctanoate by volume/weight is 5～15L/1kg, and is preferably 6～10L/1kg; Moisture or water-free organic solvent, wherein water is 2.0～8.0: 100 with the volume of organic solvent ratio, and is preferably 2.5～5.0: 100.
8. each described preparation method in requiring according to aforesaid right, it is characterized in that, the solution of resulting cephalofruxin acid solution with the moisture or water-free organic solvent of Sodium.alpha.-hydroxypropionate or Sodium isooctanoate is mixed, under 0～50 ℃ of temperature, stirred 0.5～5 hour, and the cephalofruxin sodium crystal is separated out; Filter then, wash, drying obtains Cefuroxime sodium.
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Cited By (4)
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| CN103044452A (en) * | 2013-01-10 | 2013-04-17 | 潘行远 | Preparation method of low-moisture and high-stability sterile cefuroxime sodium |
| CN104530084A (en) * | 2014-12-23 | 2015-04-22 | 天津大学 | Novel crystal form of cefuroxime sodium and preparation method of cefuroxime sodium crystal |
| CN105669700A (en) * | 2016-02-18 | 2016-06-15 | 海南灵康制药有限公司 | Cefuroxime sodium new crystal type compound and preparation adopting particle process crystal product molecular assembly and form optimizing technology |
| CN109851627A (en) * | 2018-12-21 | 2019-06-07 | 广州白云山天心制药股份有限公司 | A kind of preparation method of Cefuroxime Sodium crystal-form compound |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103044452A (en) * | 2013-01-10 | 2013-04-17 | 潘行远 | Preparation method of low-moisture and high-stability sterile cefuroxime sodium |
| CN104530084A (en) * | 2014-12-23 | 2015-04-22 | 天津大学 | Novel crystal form of cefuroxime sodium and preparation method of cefuroxime sodium crystal |
| CN105669700A (en) * | 2016-02-18 | 2016-06-15 | 海南灵康制药有限公司 | Cefuroxime sodium new crystal type compound and preparation adopting particle process crystal product molecular assembly and form optimizing technology |
| WO2017140072A1 (en) * | 2016-02-18 | 2017-08-24 | 海南灵康制药有限公司 | Novel polymorphic cefuroxime sodium compound and preparation employing particle process crystal product molecular assembly and morphological optimization technique |
| CN109851627A (en) * | 2018-12-21 | 2019-06-07 | 广州白云山天心制药股份有限公司 | A kind of preparation method of Cefuroxime Sodium crystal-form compound |
| CN109851627B (en) * | 2018-12-21 | 2022-04-12 | 广州白云山天心制药股份有限公司 | Preparation method of cefuroxime sodium crystal compound |
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Application publication date: 20111228 |