CN104341435B - The process for purification of ceftriaxone sodium - Google Patents
The process for purification of ceftriaxone sodium Download PDFInfo
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- CN104341435B CN104341435B CN201310325568.6A CN201310325568A CN104341435B CN 104341435 B CN104341435 B CN 104341435B CN 201310325568 A CN201310325568 A CN 201310325568A CN 104341435 B CN104341435 B CN 104341435B
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- sodium
- ceftriaxone sodium
- ceftriaxone
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- isooctanoate
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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
Abstract
The present invention provides the process for purification of a kind of ceftriaxone sodium, comprising: 1) crude product of ceftriaxone sodium is provided；2) in organic solvent, make crude product of ceftriaxone sodium and organic acid reaction that step 1) obtains, filter, obtain filtrate；And 3) by step 2) filtrate that obtains mixes with the organic solution of Sodium isooctanoate., crystallize, separate and obtain described ceftriaxone sodium。The present invention compared with prior art has the advantages that: the method for the present invention is not related to water solution system, so there is no the side reaction of oxidative degradation interference, gained ceftriaxone sodium quality of finished product good, solution colour is below Y3/YG3, easy and simple to handle, reduce production cost, it is easy to accomplish industrialized great production。
Description
Technical field
The invention belongs to pharmaceutical field, in particular to the process for purification of a kind of ceftriaxone sodium。
Background technology
The chemical name of ceftriaxone sodium (Ceftriaxonesodium) is: (6R, 7R)-7-[[(2-amino-4-thiazolyl) (methoxyimino) acetyl] 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 such as shown in following formula I。Ceftriaxone sodium is white or off-white color crystalline powder, has hygroscopicity, soluble in water, is slightly soluble in methanol, almost insoluble in chloroform and ether。
Formulas I
Ceftriaxone sodium is succeeded in developing in 1978 by Roche company of Switzerland, and nineteen eighty-two lists in Switzerland first, within 1984, obtains FDA certification。Ceftriaxone sodium entered since China market from nineteen ninety-five, and the consumption sum in whole body infection medication ranked first always in recent years, was one of 22 kinds of clinical cephalosporins preparation varieties of current state approval。Ceftriaxone sodium is semisynthetic Third generation Cephalosporins medicine, and it is all effective and bacteriogenic most of β-Nei acyl ammonia enzymes are stable to many gram positive bacterias and gram-negative bacteria and anaerobe, thus its bactericidal action is stronger。Clinic is 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 purification refine method of current ceftriaxone sodium includes:
1. after Chinese patent CN102432629A dissolves ceftriaxone sodium with methanol as mixed solvent with water for injection, recycling dissolved agent precipitates out finished product。This method yet suffers from the interference of oxidative degradation in subtractive process, it is necessary to deliberately add antioxidant sodium pyrosulfite。
2. Chinese patent CN101289458A discloses the process for purification of a kind of crude product of ceftriaxone sodium, adds dissolving crude product in water for injection, adds the insoluble organic solvent of ceftriaxone sodium and prepare finished product after aseptic filtration。This method is susceptible to oxidative degradation in crystallization process, affects product color level。
It can be seen that owing to ceftriaxone sodium is unstable in aqueous, easily there is oxidative degradation in from the above, therefore the color level of the product of the ceftriaxone sodium that said method is obtained is relatively big, and its solution colour is generally Y4/YG4 or Y5/YG5。Due to for ceftriaxone sodium, as the crude drug of injection, its color level is more little, will imply that the quality of product is more good, and obtained injection safety is also more high。Therefore, the process for purification of a kind of ceftriaxone sodium producing less color level under not increasing the premise of 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 the process for purification of a kind of ceftriaxone sodium。
Specifically, the present invention provides:
(1) process for purification of a kind of ceftriaxone sodium, comprising:
1) crude product of ceftriaxone sodium is provided；
2) in organic solvent, make crude product of ceftriaxone sodium and organic acid reaction that step 1) obtains, filter, obtain filtrate；And
3) by step 2) filtrate that obtains mixes with the organic solution of Sodium isooctanoate., crystallize, and separate and obtain described ceftriaxone sodium。
(2) according to method described in (1), wherein, step 2) described in organic solvent one in glycol dimethyl ether, ethylene glycol diethyl ether, butyl glycol ether and glycerol three methyl ether；It is preferably glycol dimethyl ether。
(3) according to method described in (1), wherein, step 2) described in organic acid selected from formic acid or acetic acid；It is preferably acetic acid。
(4) according to the method described in (1), wherein, the described ceftriaxone sodium in crude product of ceftriaxone sodium and described organic acid mol ratio are 1:(1-3)；It is preferably 1:(1.1-1.5)。
(5) according to method described in (1), wherein, step 2) described in filtration include aseptic filtration。
(6) according to the method described in (1), wherein, the described ceftriaxone sodium in crude product of ceftriaxone sodium is 1:(2-6 with the mol ratio of described Sodium isooctanoate .)；It is preferably 1:(3.5-4.5)。
(7) according to the method described in (1), wherein, one or more in acetone, ethyl acetate, butyl acetate, dichloromethane, chloroform, ethanol, methanol and isopropanol of the organic solvent in the organic solution of the Sodium isooctanoate. described in step 3)；It is preferably acetone。
(8) according to the method described in (1), wherein, the concentration in described organic solution of the Sodium isooctanoate. described in step 3) is 6-9mol/L；It is preferably 7-8mol/L。
(9) according to the method described in (1), wherein, the temperature of the crystallize described in step 3) is 10 DEG C-40 DEG C；It is preferably 15 DEG C-25 DEG C。
The present invention compared with prior art has the advantages that:
1. the process for purification of the present invention is not related to water solution system, so there is no the side reaction of oxidative degradation interference, therefore need not add extra adjuvant, for instance, antioxidant。Gained ceftriaxone sodium quality of finished product good, solution colour is below Y3/YG3, its content about 93%, total impurities less than 0.5%,。
2. the process for purification yield of the present invention is high, can reach more than 80%。Such as, a preferred embodiment of the present invention may be up to about 90%。
3. the process for purification of the present invention is easy and simple to handle, and agents useful for same is cheap and easily-available, and reduces production cost, is thus susceptible to realize industrialized great production。
Detailed description of the invention
Below by way of the description of detailed description of the invention, the invention will be further described, but this is not limitation of the present invention, those skilled in the art's basic thought according to the present invention, various modifications may be made or improves, but without departing from the basic thought of the present invention, all within the scope of the present invention。
Crude product of ceftriaxone sodium has been carried out substantial amounts of refining test by the present inventor, have been surprisingly found that and be dissolved in organic solvent after crude product of ceftriaxone sodium acid adjustment, salt crystallize is become again with Sodium isooctanoate., it is not related to redox side reaction interference in the process, antioxidant need not be added, therefore, it is possible to prepare the ceftriaxone sodium reaching less color level。The present inventor, on the basis of this discovery, obtains technical scheme further。
Specifically, the invention provides the process for purification of a kind of ceftriaxone sodium, comprising:
1) crude product of ceftriaxone sodium is provided；
2) in organic solvent, make crude product of ceftriaxone sodium and organic acid reaction that step 1) obtains, filter, obtain filtrate；And
3) by step 2) filtrate that obtains mixes with the organic solution of Sodium isooctanoate., crystallize, and separate and obtain described ceftriaxone sodium。
Described crude product of ceftriaxone sodium is ceftriaxone sodium solid mixture to be further purified。Crude product of ceftriaxone sodium can be prepared by this area conventional method, for instance, crude product of ceftriaxone sodium can be prepared by the method in Chinese patent CN200410155401.0。But the present invention is not limited to this。
Ceftriaxone sodium dissolubility in common are machine solvent is very low, and ceftriaxone acid then can be dissolved in organic solvent。The described ceftriaxone sodium in crude product of ceftriaxone sodium is 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 it can dissolve ceftriaxone acid。
Preferably, step 2) described in organic solvent one in glycol dimethyl ether, ethylene glycol diethyl ether, butyl glycol ether, glycerol three methyl ether；It is preferably glycol dimethyl ether。
Preferably, step 2) described in organic acid selected from formic acid or acetic acid；It is preferably acetic acid。
Preferably, the described ceftriaxone sodium in crude product of ceftriaxone sodium and described organic acid mol ratio are 1:(1-3)；It is preferably 1:(1.1-1.5)。
Preferably, step 2) described in filtration include aseptic filtration。
Preferably, before carrying out the mixing described in step 3), the organic solution of Sodium isooctanoate. is carried out aseptic filtration respectively。
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 aseptic filtration respectively。
Microorganism that may be present in solution can be removed by above-mentioned aseptic filtration step。
Step 2) filtrate that obtains is as follows with the principle that the organic solution of Sodium isooctanoate. mixes crystallize: ceftriaxone acid produces weak acid isooctyl acid as strong acid, and the product ceftriaxone sodium dissolubility in organic solvent simultaneously obtained is only small, crystallization。
Preferably, the mol ratio of the described ceftriaxone sodium in crude product of ceftriaxone sodium and described Sodium isooctanoate. is 1:(2-6)；It is preferably 1:(3.5-4.5)。
Preferably, by step 2) filtrate that obtains adds (such as, being added dropwise to) to the organic solution of Sodium isooctanoate.。
Organic solvent in the organic solution of the Sodium isooctanoate. described in step 3) is had no particular limits by the present invention, as long as it can dissolve Sodium isooctanoate.。
Preferably, one or more in acetone, ethyl acetate, butyl acetate, dichloromethane, chloroform, ethanol, methanol and isopropanol of the organic solvent in the organic solution of the Sodium isooctanoate. described in step 3)；It is preferably acetone。
Preferably, the concentration in described organic solution of the Sodium isooctanoate. described in step 3) is 6-9mol/L；It is preferably 7-8mol/L。
The present invention is to step 2) described in the ratio of organic solvent and the organic solvent in the organic solution of Sodium isooctanoate. described in step 3) have no particular limits, as long as it can dissolve ceftriaxone acid, Sodium isooctanoate. respectively。
Preferably, the temperature of the crystallize described in step 3) is 10 DEG C-40 DEG C；It is preferably 15 DEG C-25 DEG C。
In a preferred embodiment of the invention, the method comprise the steps that and crude product of ceftriaxone sodium is placed in suitable organic solvent, obtain being dissolved in the aseptic level ceftriaxone acid of organic solvent then through sucking filtration, aseptic filtration after dropping organic acid acid adjustment solution salt, it is eventually adding the Sodium isooctanoate. acetone soln after aseptic filtration and becomes salt, precipitate out ceftriaxone sodium finished product。
Wherein, described suitable organic solvent is preferably selected from: the one in glycol dimethyl ether, ethylene glycol diethyl ether；It is more preferably glycol dimethyl ether。
Wherein, described organic acid is preferably selected from: the one in formic acid, glacial acetic acid；It is more preferably glacial acetic acid。
Wherein, described crude product of ceftriaxone sodium is preferably with organic acid mol ratio: 1:(1-3)；It is more preferably: 1:(1.1-1.5)。
Wherein, the mol ratio of described crude product of ceftriaxone sodium and Sodium isooctanoate. is preferably: 1:(2-6)；It is more preferably: 1:(3.5-4.5)。
Wherein, become salt, the temperature of Crystallization Process is preferably: 10 DEG C to 40 DEG C；It is more preferably: 15 DEG C to 25 DEG C。
Mode by the following examples further explains and describes 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 is commercially, for instance, it is available from Shuai Di bio tech ltd, Xi'an。(table 1 is called for short self-control crude product) is prepared also by the method in Chinese patent CN200410155401.0。The information such as its concrete source can referring to 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 is all commercially, for instance, it is available from Qingdao Tian Xin Chemical Co., Ltd.。
In the examples below, the quality standard of ceftriaxone sodium can referring to Chinese Pharmacopoeia version in 2010。
In the examples below, the method for detecting purity of ceftriaxone sodium can referring to Chinese Pharmacopoeia version in 2010 second。
Embodiment 1
66.9g crude product of ceftriaxone sodium (wherein contains ceftriaxone sodium 66.2g(0.1mol)) it is added to stirring and evenly mixing in 250ml glycol dimethyl ether, dropping glacial acetic acid 7.2g(0.12mol), reaction 1 hour it is sufficiently stirred under room temperature (25 DEG C), sucking filtration removes insoluble solid, gained filtrate adds Sodium isooctanoate. acetone soln 50ml(containing Sodium isooctanoate. 58.2g(0.35mol at 25 DEG C)), insulated and stirred crystallize 5 hours, sucking 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 contains ceftriaxone sodium 66.2g(0.1mol)) it is added to stirring and evenly mixing in 250ml glycol dimethyl ether, dropping formic acid 5.5g(0.12mol), reaction 1 hour it is sufficiently stirred under room temperature (25 DEG C), sucking filtration removes insoluble solid, gained filtrate carries out adding the same Sodium isooctanoate. acetone soln 50ml(through aseptic filtration after aseptic process again at 25 DEG C containing Sodium isooctanoate. 33.3g(0.20mol through microporous filter membrane)), insulated and stirred crystallize 5 hours, sucking 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 contains ceftriaxone sodium 66.2g(0.1mol)) it is added to stirring and evenly mixing in 250ml glycol dimethyl ether, dropping glacial acetic acid 18.0g(0.3mol), reaction 1 hour it is sufficiently stirred under room temperature (25 DEG C), sucking filtration removes insoluble solid, gained filtrate adds Sodium isooctanoate. acetone soln 50ml(containing Sodium isooctanoate. 66.5g(0.4mol at 25 DEG C)), insulated and stirred crystallize 5 hours, sucking 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 contains ceftriaxone sodium 66.2g(0.1mol)) it is added to stirring and evenly mixing in 250ml ethylene glycol diethyl ether, dropping glacial acetic acid 7.2g(0.12mol), reaction 1 hour it is sufficiently stirred under room temperature (25 DEG C), sucking filtration removes insoluble solid, gained filtrate adds Sodium isooctanoate. acetone soln 50ml(containing Sodium isooctanoate. 99.8g(0.60mol at 25 DEG C)), insulated and stirred crystallize 5 hours, sucking 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 contains ceftriaxone sodium 66.2g(0.1mol)) it is added to stirring and evenly mixing in 250ml glycol dimethyl ether, dropping glacial acetic acid 7.2g(0.12mol), reaction 1 hour it is sufficiently stirred under room temperature (25 DEG C), sucking filtration removes insoluble solid, gained filtrate adds Sodium isooctanoate. acetone soln 50ml(containing Sodium isooctanoate. 58.2g(0.35mol at 15 DEG C)), insulated and stirred crystallize 5 hours, sucking 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
From Table 2, it can be seen that by the process for purification of the present invention, obtained ceftriaxone sodium is obviously improved in color level, and the raising of product purity also there is certain effect。
Claims (15)
1. a process for purification for ceftriaxone sodium, comprising:
1) crude product of ceftriaxone sodium is provided；
2) in organic solvent, make step 1) crude product of ceftriaxone sodium that obtains and organic acid reaction, filter, obtain filtrate, wherein, described organic solvent one in glycol dimethyl ether, ethylene glycol diethyl ether, butyl glycol ether and glycerol three methyl ether；
3) by step 2) filtrate that obtains mixes with the organic solution of Sodium isooctanoate., crystallize, and separate and obtain described ceftriaxone sodium。
2. method according to claim 1, wherein, step 2) described in organic solvent be glycol dimethyl ether。
3. method according to claim 1, wherein, step 2) described in organic acid selected from formic acid or acetic acid。
4. method according to claim 1, wherein, step 2) described in organic acid be acetic acid。
5. method according to claim 1, wherein, the described ceftriaxone sodium in crude product of ceftriaxone sodium and described organic acid mol ratio are 1:(1-3)。
6. method according to claim 1, wherein, the described ceftriaxone sodium in crude product of ceftriaxone sodium and described organic acid mol ratio are 1:(1.1-1.5)。
7. method according to claim 1, wherein, step 2) described in filtration include aseptic filtration。
8. method according to claim 1, wherein, the mol ratio of the described ceftriaxone sodium in crude product of ceftriaxone sodium and described Sodium isooctanoate. is 1:(2-6)。
9. method according to claim 1, wherein, the mol ratio of the described ceftriaxone sodium in crude product of ceftriaxone sodium and described Sodium isooctanoate. is 1:(3.5-4.5)。
10. method according to claim 1, wherein, step 3) described in Sodium isooctanoate. organic solution in one or more in acetone, ethyl acetate, butyl acetate, dichloromethane, chloroform, ethanol, methanol and isopropanol of organic solvent。
11. method according to claim 1, wherein, step 3) described in Sodium isooctanoate. organic solution in organic solvent be acetone。
12. method according to claim 1, wherein, step 3) described in Sodium isooctanoate. concentration in described organic solution be 6-9mol/L。
13. method according to claim 1, wherein, step 3) described in Sodium isooctanoate. concentration in described organic solution be 7-8mol/L。
14. method according to claim 1, wherein, step 3) described in the temperature of crystallize be 10 DEG C-40 DEG C。
15. method according to claim 1, wherein, step 3) described in the temperature of crystallize for for 15 DEG C-25 DEG C。
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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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| CN1597684A (en) * | 2003-09-16 | 2005-03-23 | 广州白云山制药股份有限公司 | Sodium ceftriaxone and its preparation method |
| CN101289458A (en) * | 2007-04-21 | 2008-10-22 | 山东瑞阳制药有限公司 | Refining process for crude product of ceftriaxone sodium |
| CN102432629A (en) * | 2011-11-14 | 2012-05-02 | 齐鲁安替制药有限公司 | Method for refining ceftriaxone sodium crude product |
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| US7098329B2 (en) * | 2003-06-19 | 2006-08-29 | Orchid Chemicals & Pharmaceuticals Ltd. | Process for the preparation of a cephalosporin antibiotic |
| US20050059820A1 (en) * | 2003-09-17 | 2005-03-17 | Debashish Datta | Method for manufacture of ceftriaxone sodium |
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| CN101289458A (en) * | 2007-04-21 | 2008-10-22 | 山东瑞阳制药有限公司 | Refining process for crude product of ceftriaxone sodium |
| CN102432629A (en) * | 2011-11-14 | 2012-05-02 | 齐鲁安替制药有限公司 | Method for refining ceftriaxone sodium crude product |
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Address after: 100871, Beijing, Haidian District Cheng Fu Road 298, founder building, 9 floor Patentee after: PEKING UNIVERSITY FOUNDER GROUP Co.,Ltd. Patentee after: PKU HEALTHCARE Corp.,Ltd. Patentee after: PKU HEALTHCARE INDUSTRY Group Address before: 100871, Beijing, Haidian District, Cheng Fu Road, No. 298, Zhongguancun Fangzheng building, 5 floor Patentee before: PEKING UNIVERSITY FOUNDER GROUP Co.,Ltd. Patentee before: SOUTHWEST SYNTHETIC PHARMACEUTICAL Corp.,Ltd. Patentee before: Pku Healthcare Industry Group Co.,Ltd. |
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Effective date of registration: 20221012 Address after: 3007, Hengqin international financial center building, No. 58, Huajin street, Hengqin new area, Zhuhai, Guangdong 519031 Patentee after: New founder holdings development Co.,Ltd. Patentee after: PKU HEALTHCARE Corp.,Ltd. Patentee after: Peking University Medical Management Co.,Ltd. Address before: 100871, Beijing, Haidian District Cheng Fu Road 298, founder building, 9 floor Patentee before: PEKING UNIVERSITY FOUNDER GROUP Co.,Ltd. Patentee before: PKU HEALTHCARE Corp.,Ltd. Patentee before: PKU HEALTHCARE INDUSTRY Group |