CN1594324A - Process for preparing cefpiramide sodium - Google Patents
Process for preparing cefpiramide sodium Download PDFInfo
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- CN1594324A CN1594324A CN 200410027956 CN200410027956A CN1594324A CN 1594324 A CN1594324 A CN 1594324A CN 200410027956 CN200410027956 CN 200410027956 CN 200410027956 A CN200410027956 A CN 200410027956A CN 1594324 A CN1594324 A CN 1594324A
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Abstract
The invention provides a process for preparing cefpiramide sodium which consists of, dissolving cefpiramide acid with dissolvent, dissolving by charging sodium converting agent, adjusting the pH value to 6.5-8.0, filtering, charging organic solvent for evolution of cefpiamide sodium, filtering, and drying to obtain the powder form.
Description
Technical field
The invention belongs to the cynnematin field, relate to a kind of preparation method of Wy-44635.
Background technology
Wy-44635 chemistry (6R by name, 7R)-7-[(R)-2-(4-hydroxyl-6-methyl-3-pyridyl carboxylic acid amido)-2-(p-hydroxybenzene) acetamido]-3-[[(1-methyl isophthalic acid H-tetrazolium-5-yl) sulphur] methyl]-8-oxo-5-thia-1-azabicyclic [4,2, O] oct-2-ene-2-carboxylic acid sodium, molecular formula: C
25H
23N
8NaO
7S
2
Structural formula:
Cefpiramide [Cefpiramide] is a third generation cephalosporin by invention in the age, by anti-microbial property belong to the 4th generation cynnematin.This product chemical structure characteristics are that 3 of cephem parent nucleus are connected to first sulphur tetrazyl, 7 side chains are connected to hydroxyphenyl and 4-hydroxymethylpiperidine, therefore this medicine had both had the anti-microbial activity of first generation cephalosporin to gram-positive microorganism, have the anti-microbial effect of third and fourth generation again to Gram-negative bacteria, and stable to β-Nei Xiananmei.Compare with other cynnematins, this product has has a broad antifungal spectrum, has good characteristics of pharmacokinetics, to beta-lactam acyl good stability, cefpiramide is to gram-positive cocci tool good antibacterial activity, simultaneously gram negative bacillus had anti-microbial activity efficiently, antimicrobial spectrum with perfect balance, this estimates the key point of new cynnematin just.
At present, Wy-44635 all is a lyophilized powder, as day disclosure special permission JP 54-125678, JP 54-30197, and European patent EP 1,985 59052, and " organic drug synthesis method " first roll 613-615 page or leaf etc. has the pertinent literature report.Because lyophilized powder is inhomogeneous, color and luster is relatively poor, purity is on the low side, the content height of related substance, product instability, be difficult for preserving, and needs with special freeze-drier and production site, thereby production cost is higher.
Summary of the invention
The object of the invention provides a kind of manufacture method of Wy-44635, and technology is simple, production cost is low, and the Wy-44635 product powder that obtains is even, color and luster good, the purity height, and impurity is few, and product is stable easily to be preserved.
The preparation method of a kind of Wy-44635 of the present invention, its technical scheme can have two kinds:
Technical scheme one: described preparation method may further comprise the steps:
A, get Cefpiramide Acid and dissolve, add the sodium transforming agent dissolving, transfer pH to 6.5～8.0, filter with solvent;
B, in filtrate, add organic solvent, this organic solvent and described solvent dissolve each other but with Wy-44635 slightly soluble or insoluble, separate out Wy-44635, filter, drying is Cefpiramide sodium powder.
Technical scheme two: described preparation method may further comprise the steps:
A, Cefpiramide Acid dissolve with solvent, add the sodium transforming agent dissolving, and filter adjust pH to 6.5～8.0;
B, with filtrate azeotropic or vacuum concentration crystallization, drying is Cefpiramide sodium powder.
In the technique scheme, in step a, the weightmeasurement ratio of Cefpiramide Acid and solvent is 1: 1～50.
Described solvent is a water, perhaps polar organic solvent, perhaps both mixed solutions.
Above-mentioned polar organic solvent is selected from C
1-6Alcohols, C
1-6One or more the combination of ketone, acetonitrile, dioxy six alkane, tetrahydrofuran (THF), DMF, DMA.Described C
1-6Alcohols is selected from a kind of of methyl alcohol, ethanol, propyl alcohol, Virahol, glycerol, isopropylcarbinol, propyl carbinol; Described C
1-6Ketone is selected from a kind of of acetone, methylethylketone, pentanone, butanone, isobutyl ketone.
In the technique scheme, described sodium transforming agent is selected from NaOH, NaHCO
3, Na
2CO
3, sodium-acetate, Sodium isooctanoate, sodium formiate, sodium phosphate, sodium hydrogen phosphate, Sodium Citrate, Sodium.alpha.-hydroxypropionate, Sunmorl N 60S, Sodium Benzoate one or more combination.
In the technique scheme, in the process of dissolving and separating out, temperature is controlled at-10～45 ℃, and preferred 0～30 ℃, and stir.
In the technique scheme, in step a, add in the sodium transforming agent dissolved process, also add stablizer.
Described stablizer is selected from one or more combination of Sodium Benzoate, vitamins C, S-WAT, sodium bisulfite.
In technical scheme one, change that the organic solvent that is added behind the sodium must dissolve each other with the solvent of preceding usefulness but with Wy-44635 slightly soluble or insoluble, thereby Wy-44635 is separated out.This organic solvent is selected from one or more the combination of alcohols, ketone, ethers, hydro carbons, nitrile, ester class, DMF, DMA.Described alcohols is selected from a kind of of methyl alcohol, ethanol, propyl alcohol, Virahol, glycerol, isopropylcarbinol, propyl carbinol; Described ketone is selected from a kind of of acetone, methylethylketone, pentanone, butanone, isobutyl ketone; Described ethers is selected from a kind of of ether, isopropyl ether, sherwood oil, dioxy six alkane, tetrahydrofuran (THF); Described hydro carbons is selected from a kind of of normal hexane, normal heptane, hexanaphthene, toluene, dimethylbenzene; Described ester class is selected from a kind of of ethyl acetate, methyl acetate, butylacetate, ethyl butyrate.
The described mode of separating out is separated out for separate out, separate out continuously, stir to separate out or leave standstill in batches.
The preferable mode of separating out is: when dripping organic solvent in filtrate, drip to just muddy, stop to drip, stirred slowly or leave standstill 0～24 hour, stir, continue to drip organic solvent, separate out fully until precipitation.
Technical scheme two is just carried out isolating principle according to solvent boiling point, earlier Wy-44635 is used mixed dissolution with solvents, at least contain the soluble solvent of a kind of Wy-44635 and a kind of Wy-44635 indissoluble or insoluble solvent in this mixed solvent, and between soluble solvent and indissoluble or the insoluble solvent evident difference is arranged on boiling point.The boiling point of soluble solvent is lower than indissoluble or insoluble solvent, earlier lower boiling soluble solvent is removed when distillation, the solubleness of Wy-44635 in residual solvent is reduced, and then separate out.
Solvent boiling point such as following table:
| Organic solvent | Boiling point |
| Methyl alcohol | 64.5℃ |
| Ethanol | 78.3℃ |
| Virahol | 82.4℃ |
The soluble solvent of Wy-44635 is a methyl alcohol among the present invention.
Advantage of the present invention is: the Cefpiramide Acid sodium powder of (1) gained is even, color and luster good, purity is high, the content of related substance is low, stable, easily preservation; (2) need not specific installation, technology is simple to operation, and batch output can be bigger, is easy to industrialization, and product can reach the purpose of the high and good stability of purity, and is with low cost.
Utilize the contrast of prepared Cefpiramide Acid sodium powder of the present invention and existing Cefpiramide Acid sodium freeze dry product to see the following form:
| Outward appearance | Color and luster | Mobile | Content | Related substance | Stability | ||
| Total impurities | MMT | ||||||
| Lyophilized powder | Powder | Relatively poor | Relatively poor | ＞90％ | ＜5.0％ | ＜0.5％ | Relatively poor |
| Solvent is separated out powder | Fine granularity | Good | Good | ＞96％ | ＜2.0％ | ＜0.2％ | Good |
Embodiment
Embodiment 1
Take by weighing Cefpiramide Acid 8.0g, add entry 30ml, stirring at room adds NaHCO
31.10g, stirred 0.5 hour, the dissolving clarification, the pH value is 7.8, filters or sterile filtration.Drip Virahol 300ml toward filtrate and separate out, leave standstill, filter, washing, vacuum-drying.Get the Wy-44635 powder.Weight 7.71 grams, yield 96.8%, related substance MMT0.18%, total impurities 1.87%.
Embodiment 2
Take by weighing Cefpiramide Acid 8.0g, add the mixed solution of entry 24ml and Virahol 8ml, add NaHCO
31.10g, when 15 ℃ of temperature, stirring 0.5 hour, dissolving clarification pH value is 6.9, filtration or sterile filtration.Drip the mixed solution 200ml of acetone and Virahol (1: 1), separate out, leave standstill, filter, washing, vacuum-drying.Get the Wy-44635 powder.Weight 7.71 grams, yield 96.4%, related substance MMT0.17%, total impurities 1.77%.
Embodiment 3
Take by weighing Cefpiramide Acid 8.0g, add the mixed solution of DMF16ml and water 8ml, add NaHCO
31.10g, when 20 ℃ of temperature, stirring 0.5 hour, dissolving clarification pH value is 7.0, filtration or sterile filtration.Drip the mixed solution 300ml of DMF and acetone (1: 50), separate out, leave standstill, filter, washing, vacuum-drying.Get the Wy-44635 powder.Weight 7.71 grams, yield 97.2%, related substance MMT0.16%, total impurities 1.82%.
Embodiment 4
Take by weighing Cefpiramide Acid 8.0g, add the mixed solution of DMF16ml and water 8ml, add Sodium isooctanoate 1.10g, when 10 ℃ of temperature, stirred 0.5 hour, dissolving clarification pH value is 7.8, filtration or sterile filtration.Drip the mixed solution 250ml of the warm and fine acetone of second (1: 30), separate out, leave standstill, filter, washing, vacuum-drying.Get the Wy-44635 powder.Weight 7.71 grams, yield 98.4%, related substance MMT0.13%, total impurities 1.84%.
Embodiment 5
Take by weighing Cefpiramide Acid 8.0g, add the mixed solution of tetrahydrofuran (THF) 16ml and water 8ml, add sodium-acetate 1.10g, when 0 ℃ of temperature, stirred 0.5 hour, dissolving clarification pH value is 6.6, filtration or sterile filtration.Drip the mixed solution 200ml of tetrahydrofuran (THF) and acetone (1: 15), separate out, leave standstill, filter, washing, vacuum-drying.Get the Wy-44635 powder.
Embodiment 6
Take by weighing Cefpiramide Acid 8.0g, add the mixed solution of fine 16ml of second and water 8ml, add NaHCO
31.10g, add Sodium Benzoate 0.52g again, when 30 ℃ of temperature, stirred 0.5 hour, dissolving clarification pH value is 7.3, filtration or sterile filtration.Drip the mixed solution 300ml of DMF and acetone (1: 10), separate out, leave standstill, filter, washing, vacuum-drying.Get the Wy-44635 powder.
Embodiment 7
Take by weighing Cefpiramide Acid 8.0g, add the mixed solution of DMF16ml and water 8ml, add NaHCO
31.10g, when 40 ℃ of temperature, stirring 0.5 hour, dissolving clarification pH value is 6.7, filtration or sterile filtration.Drip the mixed solution 300ml of Virahol and acetone (1: 10), separate out, leave standstill, filter, washing, vacuum-drying.Get the Wy-44635 powder.
Embodiment 8
Take by weighing Cefpiramide Acid 8.0g, add the mixed solution of entry 24ml and Virahol 8ml, add Sodium isooctanoate 1.10g, when temperature-5 ℃, stirred 0.5 hour, dissolving clarification pH value is 6.5, filtration or sterile filtration.Drip the mixed solution 200ml of acetone and Virahol (1: 1), separate out, leave standstill, filter, washing, vacuum-drying.Get the Wy-44635 powder.
Embodiment 9
Take by weighing Cefpiramide Acid 8.0g, add the mixed solution of entry 24ml and Virahol 8ml, add sodium-acetate 1.10g, when 5 ℃ of temperature, stirred 0.5 hour, dissolving clarification pH value is 7.5, filtration or sterile filtration.Drip the mixed solution 250ml of tetrahydrofuran (THF) and Virahol (15: 1), separate out, leave standstill, filter, washing, vacuum-drying.Get the Wy-44635 powder.
Embodiment 10
Take by weighing Cefpiramide Acid 8.0g, add the mixed solution of entry 24ml and Virahol 8ml, add NaHCO
31.10g, add Sodium Benzoate 0.52g again, when 35 ℃ of temperature, stirred 0.5 hour, dissolving clarification pH value is 6.6, filtration or sterile filtration.Drip the mixed solution of acetone and Virahol (1: 1), separate out, leave standstill, filter, washing, vacuum-drying.Get the Wy-44635 powder.
Embodiment 11
Take by weighing Cefpiramide Acid 8.0g, add the mixed solution of acetone 40ml and the fine 35ml of second, add NaHCO
31.10g, when 20 ℃ of temperature, stirring 0.5 hour, dissolving clarification pH value is 7.8, filtration or sterile filtration.Drip isopropyl ether, separate out and leave standstill, filter, washing, vacuum-drying.Get the Wy-44635 powder.
Embodiment 12
Take by weighing Cefpiramide Acid 8.0g, add acetone 30ml, stirring at room adds NaHCO
31.10g, adding Sodium Benzoate 0.52g again and stirred 0.5 hour, dissolving clarification pH value is 7.2, filters or sterile filtration.Drip toluene toward filtrate and separate out, leave standstill, filter, washing, vacuum-drying.Get the Wy-44635 powder.
Embodiment 13
Take by weighing Cefpiramide Acid 8.0g, add ethanol 230ml, when 10 ℃ of temperature, stir, add NaHCO
31.10g vitaminize C0.20g stirred 0.5 hour again, dissolving clarification pH value is 6.7, filters or sterile filtration.Drip normal heptane toward filtrate and separate out, leave standstill, filter, washing, vacuum-drying.Get the Wy-44635 powder.
Embodiment 14
Take by weighing Cefpiramide Acid 8.0g, add entry 10ml and acetone 20ml, stirring at room adds NaHCO
31.10g, adding S-WAT 0.45g again and stirred 0.5 hour, dissolving clarification pH value is 7.6, filters or sterile filtration.Drip ethyl acetate toward filtrate and separate out, leave standstill, filter, washing, vacuum-drying.Get the Wy-44635 powder.
Embodiment 15
Take by weighing Cefpiramide Acid 8.0g, add methyl alcohol 250ml, stirring at room adds Sodium isooctanoate 1.10g, adds S-WAT 0.45g again and stirs 0.5 hour, dissolving clarification pH value is 7.1, filtration or sterile filtration, and the filtrate vacuum concentration is to 20ml, crystallization, leave standstill, filter, washing, vacuum-drying.Get the Wy-44635 powder.
Embodiment 16
Take by weighing Cefpiramide Acid 8.0g, add methyl alcohol 300ml and Virahol 50ml, stirring at room, add Sodium isooctanoate 1.10g, add S-WAT 0.45g again and stirred 0.5 hour, dissolving clarification pH value is 6.6, filters or sterile filtration, filtrate concentrating under reduced pressure under 20 ℃ temperature is removed methyl alcohol, has more solid to separate out in solution.Can add Virahol in case of necessity, remove methyl alcohol to steam as much as possible.After leaving standstill 2 hours, filter washing, vacuum-drying.Get the Wy-44635 powder.
Claims (11)
1, a kind of preparation method of Wy-44635 is characterized in that may further comprise the steps:
A, get Cefpiramide Acid and dissolve, add the sodium transforming agent dissolving, transfer pH to 6.5～8.0, filter with solvent;
B, in filtrate, add organic solvent, this organic solvent and described solvent dissolve each other but with Wy-44635 slightly soluble or insoluble, separate out Wy-44635, filter, drying is Cefpiramide sodium powder.
2, a kind of preparation method of Wy-44635 is characterized in that may further comprise the steps:
A, get Cefpiramide Acid and dissolve with solvent, add the sodium transforming agent dissolving, filter adjust pH to 6.5～8.0;
B, with filtrate azeotropic or vacuum concentration crystallization, drying is Cefpiramide sodium powder.
3, preparation method according to claim 1 and 2 is characterized in that: in step a, the weightmeasurement ratio of Cefpiramide Acid and solvent is 1: 1～50.
4, preparation method according to claim 1 and 2 is characterized in that: described solvent is a water, perhaps polar organic solvent, perhaps both mixed solutions.
5, preparation method according to claim 4 is characterized in that: described polar organic solvent is selected from C
1-6Alcohols, C
1-6One or more the combination of ketone, acetonitrile, dioxy six alkane, tetrahydrofuran (THF), DMF, DMA.
6, preparation method according to claim 1 and 2 is characterized in that: described sodium transforming agent is selected from NaOH, NaHCO
3, Na
2CO
3, sodium-acetate, Sodium isooctanoate, sodium formiate, sodium phosphate, sodium hydrogen phosphate, Sodium Citrate, Sodium.alpha.-hydroxypropionate, Sunmorl N 60S, Sodium Benzoate one or more combination.
7, preparation method according to claim 1 is characterized in that: the described organic solvent that is used to separate out Wy-44635 is selected from one or more the combination of alcohols, ketone, ethers, hydro carbons, nitrile, ester class, DMF, DMA.
8, according to claim 5 or 7 described preparation methods, it is characterized in that:
Described alcohols is selected from a kind of of methyl alcohol, ethanol, propyl alcohol, Virahol, glycerol, isopropylcarbinol, propyl carbinol;
Described ketone is selected from a kind of of acetone, methylethylketone, pentanone, butanone, isobutyl ketone;
Described ethers is selected from a kind of of ether, isopropyl ether, sherwood oil, dioxy six alkane, tetrahydrofuran (THF);
Described hydro carbons is selected from a kind of of normal hexane, normal heptane, hexanaphthene, toluene, dimethylbenzene;
Described ester class is selected from a kind of of ethyl acetate, methyl acetate, butylacetate, ethyl butyrate.
9, preparation method according to claim 1 is characterized in that separating out mode and is: when dripping organic solvent in filtrate, drip to just muddy, stop to drip, stirred slowly or leave standstill 0～24 hour, stir, continue to drip organic solvent, separate out fully until precipitation.
10, preparation method according to claim 1 and 2 is characterized in that: in step a, add in the sodium transforming agent dissolved process, also add stablizer.
11, preparation method according to claim 10 is characterized in that: described stablizer is selected from one or more combination of Sodium Benzoate, vitamins C, S-WAT, sodium bisulfite.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2004100279567A CN1305877C (en) | 2004-07-07 | 2004-07-07 | Process for preparing cefpiramide sodium |
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|---|---|---|---|
| CNB2004100279567A CN1305877C (en) | 2004-07-07 | 2004-07-07 | Process for preparing cefpiramide sodium |
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| Publication Number | Publication Date |
|---|---|
| CN1594324A true CN1594324A (en) | 2005-03-16 |
| CN1305877C CN1305877C (en) | 2007-03-21 |
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|---|---|---|---|
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100480251C (en) * | 2007-04-18 | 2009-04-22 | 武汉同源药业有限公司 | Method for synthesizing compound of cefpiramide sodium |
| CN101838276A (en) * | 2010-05-17 | 2010-09-22 | 胡梨芳 | Cefpiramide sodium hydrate and preparation method and application thereof |
| CN102040507A (en) * | 2009-10-10 | 2011-05-04 | 台州市华南医化有限公司 | Preparation methods of 7-phenyl-6-heptynoic acid and reactant of sodium 5-bromo-pentanoate |
| CN102053078A (en) * | 2010-11-12 | 2011-05-11 | 内蒙古科技大学 | Fluorimetric determination method of cefpiramide sodium for injection |
| CN103059048A (en) * | 2011-10-21 | 2013-04-24 | 珠海保税区丽珠合成制药有限公司 | Method for preparing cefpiramide acid |
| CN103319505A (en) * | 2013-06-07 | 2013-09-25 | 华北制药河北华民药业有限责任公司 | Method for crystallizing and producing cefpiramide sodium crystals |
| CN107951842A (en) * | 2017-12-21 | 2018-04-24 | 广州白云山天心制药股份有限公司 | A kind of preparation method of micro mist cefpiramide |
| CN109369683A (en) * | 2018-11-01 | 2019-02-22 | 华北制药河北华民药业有限责任公司 | A kind of preparation method of CefPiramide Sodium |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5762284A (en) * | 1980-10-01 | 1982-04-15 | Sumitomo Chem Co Ltd | Stabilizing method |
| KR950010155B1 (en) * | 1992-10-10 | 1995-09-11 | 주식회사종근당 | Sefpyramide preparation for rapid soluble injection |
| CN1164593C (en) * | 2002-07-05 | 2004-09-01 | 上海新亚药业有限公司 | Method for synthesizing cefotaxime sodium |
-
2004
- 2004-07-07 CN CNB2004100279567A patent/CN1305877C/en not_active Expired - Lifetime
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN100480251C (en) * | 2007-04-18 | 2009-04-22 | 武汉同源药业有限公司 | Method for synthesizing compound of cefpiramide sodium |
| CN102040507A (en) * | 2009-10-10 | 2011-05-04 | 台州市华南医化有限公司 | Preparation methods of 7-phenyl-6-heptynoic acid and reactant of sodium 5-bromo-pentanoate |
| CN102040507B (en) * | 2009-10-10 | 2013-12-04 | 台州市华南医化有限公司 | Preparation methods of 7-phenyl-6-heptynoic acid and reactant of sodium 5-bromo-pentanoate |
| CN102906100A (en) * | 2010-05-17 | 2013-01-30 | 胡梨芳 | Cefpiramide sodium hydrate, preparation method and uses thereof |
| CN101838276A (en) * | 2010-05-17 | 2010-09-22 | 胡梨芳 | Cefpiramide sodium hydrate and preparation method and application thereof |
| WO2011144021A1 (en) * | 2010-05-17 | 2011-11-24 | 胡梨芳 | Cefpiramide sodium hydrate, preparation method and uses thereof |
| CN101838276B (en) * | 2010-05-17 | 2012-10-10 | 胡梨芳 | Cefpiramide sodium hydrate and preparation method and application thereof |
| CN102053078A (en) * | 2010-11-12 | 2011-05-11 | 内蒙古科技大学 | Fluorimetric determination method of cefpiramide sodium for injection |
| CN102053078B (en) * | 2010-11-12 | 2012-07-04 | 内蒙古科技大学 | Fluorimetric determination method of cefpiramide sodium for injection |
| CN103059048A (en) * | 2011-10-21 | 2013-04-24 | 珠海保税区丽珠合成制药有限公司 | Method for preparing cefpiramide acid |
| CN103319505A (en) * | 2013-06-07 | 2013-09-25 | 华北制药河北华民药业有限责任公司 | Method for crystallizing and producing cefpiramide sodium crystals |
| CN107951842A (en) * | 2017-12-21 | 2018-04-24 | 广州白云山天心制药股份有限公司 | A kind of preparation method of micro mist cefpiramide |
| CN107951842B (en) * | 2017-12-21 | 2020-03-27 | 广州白云山天心制药股份有限公司 | Preparation method of micro-powder cefpiramide |
| CN109369683A (en) * | 2018-11-01 | 2019-02-22 | 华北制药河北华民药业有限责任公司 | A kind of preparation method of CefPiramide Sodium |
| CN109369683B (en) * | 2018-11-01 | 2020-04-07 | 华北制药河北华民药业有限责任公司 | Preparation method of cefpiramide sodium |
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