CN104341435A - Ceftriaxone sodium purifying method - Google Patents
Ceftriaxone sodium purifying method Download PDFInfo
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- CN104341435A CN104341435A CN201310325568.6A CN201310325568A CN104341435A CN 104341435 A CN104341435 A CN 104341435A CN 201310325568 A CN201310325568 A CN 201310325568A CN 104341435 A CN104341435 A CN 104341435A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/02—Preparation
- C07D501/12—Separation; Purification
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/36—Methylene radicals, substituted by sulfur atoms
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
Abstract
The invention provides a ceftriaxone sodium purifying method. The method comprises the following steps: 1, providing crude ceftriaxone sodium; 2, reacting the crude ceftriaxone sodium with an organic acid in an organic solvent, and filtering to obtain a filtrate; and 3, mixing the filtrate obtained in step 1 with an organic solution of sodium iso-octoate, crystallizing, and separating to obtain ceftriaxone sodium. Compared with the prior art, the method not involved with an aqueous solution system has the advantages of no interference by oxidation degradation side reactions, good quality of the obtained finished ceftriaxone sodium, solution color lower than Y3/YG3, simple operation, production cost reduction, and easy realization of the industrial large scale production.
Description
Technical field
The invention belongs to pharmacy field, in particular to a kind of process for purification of ceftriaxone sodium.
Background technology
The chemical name of ceftriaxone sodium (Ceftriaxone sodium) is: (6R, 7R)-7-[[(2-amino-4-thiazolyl) (methoxyimino) acetyl] is amino]-8-oxo-3-[[(1,2,5,6-tetrahydrochysene-2-methyl-5,6-dioxo-1,2,4-triazine-3-base) sulfo-] methyl]-5-sulfo--1-azabicyclo [4.2.0] oct-2-ene-2-carboxylic acid sodium, its chemical formula is as shown in the formula shown in I.Ceftriaxone sodium is white or off-white color crystalline powder, has water absorbability, soluble in water, is slightly soluble in methyl alcohol, almost insoluble in chloroform and ether.
Formula I
Ceftriaxone sodium is succeeded in developing in 1978 by Roche company of Switzerland, and nineteen eighty-two, first in Switzerland's listing, obtains FDA certification in 1984.Ceftriaxone sodium is since nineteen ninety-five enters China market, and the consumption sum in recent years in the anti-infective medication of whole body ranks first always, is one of 22 kinds of clinical cephalosporin analog antibiotic preparation varieties of current state approval.Ceftriaxone sodium is semisynthetic Third generation Cephalosporins medicine, its to many gram positive organisms and gram-negative bacteria and anerobe all effective, and bacteriogenic most of β-Nei acyl ammonia enzyme to be stablized, thus its germicidal action is stronger.Clinically be mainly used in lower respiratory infection, urinary tract and biliary tract infection, abdominal cavity infection, pelvic infection, septicemia, skin structure infections, bone joint infection and postoperative infection and average of operation periods infection mitigation.
The common process for purification refine of current ceftriaxone sodium comprises:
1. Chinese patent CN102432629A recycles dissolved agent after dissolving ceftriaxone sodium with water for injection and methyl alcohol as mixed solvent and separates out finished product.Still there is the interference of oxidative degradation in present method, need deliberately to add antioxidant Sodium Pyrosulfite in treating process.
2. Chinese patent CN101289458A discloses a kind of process for purification of crude product of ceftriaxone sodium, in water for injection, add dissolving crude product, adds the insoluble organic solvent of ceftriaxone sodium and obtain finished product after Sterile Filtration.Easily there is oxidative degradation in present method, affect product look level in crystallisation process.
As can be seen from aforesaid method, because ceftriaxone sodium is unstable in aqueous, easily oxidative degradation occurs, therefore the look level of the product of ceftriaxone sodium that obtains of aforesaid method is comparatively large, and its solution colour is generally Y4/YG4 or Y5/YG5.Due to for ceftriaxone sodium, as the bulk drug of injection, its look level is less, and will mean that the quality of product is better, obtained injection security is also higher.Therefore, a kind of process for purification producing the ceftriaxone sodium of less look level under the prerequisite not increasing production cost and production cycle is needed at present badly.
Summary of the invention
For solving above-mentioned problems of the prior art, the invention provides a kind of process for purification of ceftriaxone sodium.
Specifically, the invention provides:
(1) process for purification for ceftriaxone sodium, it comprises:
1) crude product of ceftriaxone sodium is provided;
2) in organic solvent, the crude product of ceftriaxone sodium that step 1) is obtained and organic acid reaction, filter, obtain filtrate; And
3) by step 2) filtrate that obtains mixes with the organic solution of Sodium isooctanoate, and crystallization, is separated and obtains described ceftriaxone sodium.
(2) method Gen Ju (1), wherein, step 2) described in organic solvent be selected from the one of glycol dimethyl ether, ethylene glycol diethyl ether, butyl glycol ether and glycerol three in methyl ether; Be preferably glycol dimethyl ether.
(3) method Gen Ju (1), wherein, step 2) described in organic acid be selected from formic acid or acetic acid; Be preferably acetic acid.
(4) method Gen Ju (1), wherein, the ceftriaxone sodium in described crude product of ceftriaxone sodium and described organic acid mol ratio are 1:(1-3); Be preferably 1:(1.1-1.5).
(5) method Gen Ju (1), wherein, step 2) described in filtration comprise sterile filtration.
(6) method Gen Ju (1), wherein, the mol ratio of the ceftriaxone sodium in described crude product of ceftriaxone sodium and described Sodium isooctanoate is 1:(2-6); Be preferably 1:(3.5-4.5).
(7) method Gen Ju (1), wherein, the organic solvent in the organic solution of the Sodium isooctanoate described in step 3) is selected from one or more in acetone, ethyl acetate, butylacetate, methylene dichloride, trichloromethane, ethanol, methyl alcohol and Virahol; Be preferably acetone.
(8) method Gen Ju (1), wherein, the concentration of the Sodium isooctanoate described in step 3) in described organic solution is 6-9mol/L; Be preferably 7-8mol/L.
(9) method Gen Ju (1), wherein, the temperature of the crystallization described in step 3) is 10 DEG C-40 DEG C; Be preferably 15 DEG C-25 DEG C.
The present invention compared with prior art has the following advantages and positively effect:
1. process for purification of the present invention does not relate to water solution system, so there is no the side reaction interference of oxidative degradation, does not therefore need to add extra auxiliary material, such as, and antioxidant.Gained ceftriaxone sodium quality of finished product good, solution colour all lower than Y3/YG3, its content about 93%, total impurities is less than 0.5%.
2. process for purification yield of the present invention is high, can reach more than 80%.Such as, a preferred embodiment of the present invention can up to about 90%.
3. process for purification of the present invention is easy and simple to handle, and agents useful for same is cheaply easy to get, and reduces production cost, is therefore easy to realize industrialized production.
Embodiment
Below by way of the description of embodiment, the invention will be further described, but this is not limitation of the present invention, those skilled in the art are according to basic thought of the present invention, various amendment or improvement can be made, but only otherwise depart from basic thought of the present invention, all within the scope of the present invention.
The present inventor has carried out a large amount of refining tests to crude product of ceftriaxone sodium, have been surprisingly found that and be dissolved in organic solvent by after crude product of ceftriaxone sodium acid adjustment, use Sodium isooctanoate salify crystallization again, do not relate to redox side reaction interference in the process, antioxidant need not be added, therefore, it is possible to the obtained ceftriaxone sodium reaching less look level.The present inventor, on the basis that this finds, obtains technical scheme of the present invention further.
Specifically, the invention provides a kind of process for purification of ceftriaxone sodium, it comprises:
1) crude product of ceftriaxone sodium is provided;
2) in organic solvent, the crude product of ceftriaxone sodium that step 1) is obtained and organic acid reaction, filter, obtain filtrate; And
3) by step 2) filtrate that obtains mixes with the organic solution of Sodium isooctanoate, and crystallization, is separated and obtains described ceftriaxone sodium.
Described crude product of ceftriaxone sodium is ceftriaxone sodium solid mixture to be further purified.Crude product of ceftriaxone sodium prepares by this area ordinary method, such as, prepares crude product of ceftriaxone sodium by the method in Chinese patent CN200410155401.0.But the present invention is not limited to this.
Ceftriaxone sodium is to common are the solubleness in machine solvent very low, and ceftriaxone acid then can be dissolved in organic solvent.Ceftriaxone sodium in described crude product of ceftriaxone sodium by being obtained by reacting ceftriaxone acid with described organic acid, and is dissolved in step 2) described in organic solvent in.The present invention is to step 2) described in organic solvent have no particular limits, as long as its can dissolve ceftriaxone acid.
Preferably, step 2) described in organic solvent be selected from one in glycol dimethyl ether, ethylene glycol diethyl ether, butyl glycol ether, glycerol three methyl ether; Be preferably glycol dimethyl ether.
Preferably, step 2) described in organic acid be selected from formic acid or acetic acid; Be preferably acetic acid.
Preferably, the ceftriaxone sodium in described crude product of ceftriaxone sodium and described organic acid mol ratio are 1:(1-3); Be preferably 1:(1.1-1.5).
Preferably, step 2) described in filtration comprise sterile filtration.
Preferably, before carrying out the mixing described in step 3), respectively sterile filtration is carried out to the organic solution of Sodium isooctanoate.
It is further preferred that by step 2) before the filtrate that obtains mixes with the organic solution of Sodium isooctanoate, to step 2) organic solution of the filtrate that obtains and Sodium isooctanoate carries out sterile filtration respectively.
The microorganism that may exist in solution can be removed by above-mentioned aseptic filtration step.
Step 2) filtrate and the organic solution of Sodium isooctanoate that the obtain principle that mixes crystallization is as follows: ceftriaxone acid produces weak acid isocaprylic acid as strong acid, and the product ceftriaxone sodium simultaneously obtained in organic solvent solubleness is very little, crystallization.
Preferably, the mol ratio of the ceftriaxone sodium in described crude product of ceftriaxone sodium and described Sodium isooctanoate is 1:(2-6); Be preferably 1:(3.5-4.5).
Preferably, by step 2) filtrate that obtains adds (such as, being added dropwise to) in the organic solution of Sodium isooctanoate.
The present invention has no particular limits the organic solvent in the organic solution of the Sodium isooctanoate described in step 3), as long as it can dissolve Sodium isooctanoate.
Preferably, the organic solvent in the organic solution of the Sodium isooctanoate described in step 3) is selected from one or more in acetone, ethyl acetate, butylacetate, methylene dichloride, trichloromethane, ethanol, methyl alcohol and Virahol; Be preferably acetone.
Preferably, the concentration of the Sodium isooctanoate described in step 3) in described organic solution is 6-9mol/L; Be preferably 7-8mol/L.
The present invention is to step 2) described in organic solvent and Sodium isooctanoate described in step 3) organic solution in the ratio of organic solvent have no particular limits, as long as it can dissolve ceftriaxone acid, Sodium isooctanoate respectively.
Preferably, the temperature of the crystallization described in step 3) is 10 DEG C-40 DEG C; Be preferably 15 DEG C-25 DEG C.
In a preferred embodiment of the invention, method of the present invention comprises: crude product of ceftriaxone sodium is placed in suitable organic solvent, obtain through suction filtration, sterile filtration the aseptic level ceftriaxone acid being dissolved in organic solvent again after dripping organic acid acid adjustment solution salt, finally add the Sodium isooctanoate acetone soln salify after sterile filtration, separate out ceftriaxone sodium finished product.
Wherein, described suitable organic solvent is preferably selected from: the one in glycol dimethyl ether, ethylene glycol diethyl ether; Be more preferably glycol dimethyl ether.
Wherein, described organic acid is preferably selected from: the one in formic acid, Glacial acetic acid; Be more preferably Glacial acetic acid.
Wherein, described crude product of ceftriaxone sodium and organic acid mol ratio are preferably: 1:(1-3); Be more preferably: 1:(1.1-1.5).
Wherein, described crude product of ceftriaxone sodium and the mol ratio of Sodium isooctanoate are preferably: 1:(2-6); Be more preferably: 1:(3.5-4.5).
Wherein, the temperature of salify, Crystallization Process is preferably: 10 DEG C to 40 DEG C; Be more preferably: 15 DEG C to 25 DEG C.
Mode by the following examples further explains and describes content of the present invention, but these embodiments are not to be construed as limiting the scope of the invention.
In the examples below, crude product of ceftriaxone sodium commercially, such as, can derive from Shuai Di bio tech ltd, Xi'an.Also prepare (in table 1, being called for short self-control crude product) by the method in Chinese patent CN200410155401.0.The information such as its concrete source can see table 1.
Table 1
| Crude product of ceftriaxone sodium | Source | Color |
| Embodiment 1 | Shuai Di bio tech ltd, Xi'an | ＜Y5/YG5 |
| Embodiment 2 | Self-control crude product | ＜Y6/YG6 |
| Embodiment 3 | Self-control crude product | ＜Y6/YG6 |
| Embodiment 4 | Self-control crude product | ＜Y5/YG5 |
| Embodiment 5 | Self-control crude product | Y6/YG6 |
In the examples below, if no special instructions, each reagent all commercially, such as, can derive from Qingdao Tian Xin Chemical Co., Ltd..
In the examples below, the quality standard of ceftriaxone sodium can see Chinese Pharmacopoeia version in 2010.
In the examples below, the method for detecting purity of ceftriaxone sodium can see Chinese Pharmacopoeia version in 2010 second.
Embodiment 1
66.9g crude product of ceftriaxone sodium (wherein containing ceftriaxone sodium 66.2g(0.1mol)) be added to stirring and evenly mixing in 250ml glycol dimethyl ether, drip glacial acetic acid 7.2g(0.12mol), abundant stirring reaction 1 hour under room temperature (25 DEG C), suction filtration removing insoluble solid, gained filtrate adds Sodium isooctanoate acetone soln 50ml(containing Sodium isooctanoate 58.2g(0.35mol at 25 DEG C)), insulated and stirred crystallization 5 hours, suction filtration, filter cake 150ml acetone repeatedly drip washing.Decompression drying at 40 DEG C, obtains finished product 59.3g, yield 89.6%.Quality condition is in table 2.
Embodiment 2
66.8g crude product of ceftriaxone sodium (wherein containing ceftriaxone sodium 66.2g(0.1mol)) be added to stirring and evenly mixing in 250ml glycol dimethyl ether, drip formic acid 5.5g(0.12mol), abundant stirring reaction 1 hour under room temperature (25 DEG C), suction filtration removing insoluble solid, gained filtrate carries out at 25 DEG C, adding the same Sodium isooctanoate acetone soln 50ml(through sterile filtration after aseptically process again containing Sodium isooctanoate 33.3g(0.20mol through millipore filtration)), insulated and stirred crystallization 5 hours, suction filtration, filter cake 150ml acetone repeatedly drip washing.Decompression drying at 40 DEG C, obtains finished product 58.4g, yield 88.2%.Quality condition is in table 2.
Embodiment 3
66.8g crude product of ceftriaxone sodium (wherein containing ceftriaxone sodium 66.2g(0.1mol)) be added to stirring and evenly mixing in 250ml glycol dimethyl ether, drip glacial acetic acid 18.0g(0.3mol), abundant stirring reaction 1 hour under room temperature (25 DEG C), suction filtration removing insoluble solid, gained filtrate adds Sodium isooctanoate acetone soln 50ml(containing Sodium isooctanoate 66.5g(0.4mol at 25 DEG C)), insulated and stirred crystallization 5 hours, suction filtration, filter cake 150ml acetone repeatedly drip washing.Decompression drying at 40 DEG C, obtains finished product 59.8g, yield 90.3%.Quality condition is in table 2.
Embodiment 4
66.9g crude product of ceftriaxone sodium (wherein containing ceftriaxone sodium 66.2g(0.1mol)) be added to stirring and evenly mixing in 250ml ethylene glycol diethyl ether, drip glacial acetic acid 7.2g(0.12mol), abundant stirring reaction 1 hour under room temperature (25 DEG C), suction filtration removing insoluble solid, gained filtrate adds Sodium isooctanoate acetone soln 50ml(containing Sodium isooctanoate 99.8g(0.60mol at 25 DEG C)), insulated and stirred crystallization 5 hours, suction filtration, filter cake 150ml acetone repeatedly drip washing.Decompression drying at 40 DEG C, obtains finished product 57.7g, yield 87.2%.Quality condition is in table 2.
Embodiment 5
67.0g crude product of ceftriaxone sodium (wherein containing ceftriaxone sodium 66.2g(0.1mol)) be added to stirring and evenly mixing in 250ml glycol dimethyl ether, drip glacial acetic acid 7.2g(0.12mol), abundant stirring reaction 1 hour under room temperature (25 DEG C), suction filtration removing insoluble solid, gained filtrate adds Sodium isooctanoate acetone soln 50ml(containing Sodium isooctanoate 58.2g(0.35mol at 15 DEG C)), insulated and stirred crystallization 5 hours, suction filtration, filter cake 150ml acetone repeatedly drip washing.Decompression drying at 40 DEG C, obtains finished product 60.2g, yield 90.9%.Quality condition is in table 2.
Table 2
As can be seen from Table 2, by process for purification of the present invention, the ceftriaxone sodium obtained improves obviously in look level, and also has certain effect to the raising of product purity.
Claims (9)
1. a process for purification for ceftriaxone sodium, it comprises:
1) crude product of ceftriaxone sodium is provided;
2) in organic solvent, the crude product of ceftriaxone sodium that step 1) is obtained and organic acid reaction, filter, obtain filtrate; And
3) by step 2) filtrate that obtains mixes with the organic solution of Sodium isooctanoate, and crystallization, is separated and obtains described ceftriaxone sodium.
2. method according to claim 1, wherein, step 2) described in organic solvent be selected from the one of glycol dimethyl ether, ethylene glycol diethyl ether, butyl glycol ether and glycerol three in methyl ether; Be preferably glycol dimethyl ether.
3. method according to claim 1, wherein, step 2) described in organic acid be selected from formic acid or acetic acid; Be preferably acetic acid.
4. method according to claim 1, wherein, the ceftriaxone sodium in described crude product of ceftriaxone sodium and described organic acid mol ratio are 1:(1-3); Be preferably 1:(1.1-1.5).
5. method according to claim 1, wherein, step 2) described in filtration comprise sterile filtration.
6. method according to claim 1, wherein, the mol ratio of the ceftriaxone sodium in described crude product of ceftriaxone sodium and described Sodium isooctanoate is 1:(2-6); Be preferably 1:(3.5-4.5).
7. method according to claim 1, wherein, the organic solvent in the organic solution of the Sodium isooctanoate described in step 3) is selected from one or more in acetone, ethyl acetate, butylacetate, methylene dichloride, trichloromethane, ethanol, methyl alcohol and Virahol; Be preferably acetone.
8. method according to claim 1, wherein, the concentration of the Sodium isooctanoate described in step 3) in described organic solution is 6-9mol/L; Be preferably 7-8mol/L.
9. method according to claim 1, wherein, the temperature of the crystallization described in step 3) is 10 DEG C-40 DEG C; Be preferably 15 DEG C-25 DEG C.
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Cited By (4)
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| CN106432275A (en) * | 2016-09-21 | 2017-02-22 | 临沂草之美医药科技有限公司 | Method for preparing crystalline ceftriaxone sodium compound as drug for treating surgical infection |
| CN106432274A (en) * | 2016-09-21 | 2017-02-22 | 临沂草之美医药科技有限公司 | Crystalline compound of drug ceftriaxone sodium for treating surgical operation infections |
| CN106432279A (en) * | 2016-09-23 | 2017-02-22 | 临沂草之美医药科技有限公司 | Method for preparing medicine ceftriaxone sodium crystal compound for treating surgical infection |
| CN106432278A (en) * | 2016-09-23 | 2017-02-22 | 临沂草之美医药科技有限公司 | Crystalline compound of drug ceftriaxone sodium for treating surgical operation infections |
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| CN106432278A (en) * | 2016-09-23 | 2017-02-22 | 临沂草之美医药科技有限公司 | Crystalline compound of drug ceftriaxone sodium for treating surgical operation infections |
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| CN104341435B (en) | 2016-06-22 |
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