WO2008132574A1 - Purification of cefuroxime acid - Google Patents
Purification of cefuroxime acid Download PDFInfo
- Publication number
- WO2008132574A1 WO2008132574A1 PCT/IB2008/000983 IB2008000983W WO2008132574A1 WO 2008132574 A1 WO2008132574 A1 WO 2008132574A1 IB 2008000983 W IB2008000983 W IB 2008000983W WO 2008132574 A1 WO2008132574 A1 WO 2008132574A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- acid
- cefuroxime
- purification
- mixture
- adjusting
- Prior art date
Links
- 229960001668 cefuroxime Drugs 0.000 title claims abstract description 25
- JFPVXVDWJQMJEE-IZRZKJBUSA-N cefuroxime Chemical compound N([C@@H]1C(N2C(=C(COC(N)=O)CS[C@@H]21)C(O)=O)=O)C(=O)\C(=N/OC)C1=CC=CO1 JFPVXVDWJQMJEE-IZRZKJBUSA-N 0.000 title claims abstract description 25
- 238000000746 purification Methods 0.000 title claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 238000002835 absorbance Methods 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- 239000000047 product Substances 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 5
- 239000002585 base Substances 0.000 claims description 5
- 239000003880 polar aprotic solvent Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 239000000706 filtrate Substances 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 2
- 239000001117 sulphuric acid Substances 0.000 claims description 2
- 235000011149 sulphuric acid Nutrition 0.000 claims description 2
- JFPVXVDWJQMJEE-SWWZKJRFSA-N 55268-75-2 Chemical compound N([C@@H]1C(N2C(=C(COC(N)=O)CS[C@@H]21)C(O)=O)=O)C(=O)/C(=N/OC)C1=CC=CO1 JFPVXVDWJQMJEE-SWWZKJRFSA-N 0.000 abstract description 3
- 239000000243 solution Substances 0.000 description 8
- KEJCWVGMRLCZQQ-YJBYXUATSA-N Cefuroxime axetil Chemical compound N([C@@H]1C(N2C(=C(COC(N)=O)CS[C@@H]21)C(=O)OC(C)OC(C)=O)=O)C(=O)\C(=N/OC)C1=CC=CO1 KEJCWVGMRLCZQQ-YJBYXUATSA-N 0.000 description 7
- 229960002620 cefuroxime axetil Drugs 0.000 description 7
- URDOHUPGIOGTKV-JTBFTWTJSA-M Cefuroxime sodium Chemical compound [Na+].N([C@@H]1C(N2C(=C(COC(N)=O)CS[C@@H]21)C([O-])=O)=O)C(=O)\C(=N/OC)C1=CC=CO1 URDOHUPGIOGTKV-JTBFTWTJSA-M 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 229960000534 cefuroxime sodium Drugs 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 2
- IKWLIQXIPRUIDU-ZCFIWIBFSA-N (6r)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=CCS[C@@H]2CC(=O)N12 IKWLIQXIPRUIDU-ZCFIWIBFSA-N 0.000 description 1
- OUSLHGWWWMRAIG-FBCAJUAOSA-N (6r,7r)-7-[[(2z)-2-(furan-2-yl)-2-methoxyiminoacetyl]amino]-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound N([C@@H]1C(N2C(=C(CO)CS[C@@H]21)C(O)=O)=O)C(=O)\C(=N/OC)C1=CC=CO1 OUSLHGWWWMRAIG-FBCAJUAOSA-N 0.000 description 1
- 108020004256 Beta-lactamase Proteins 0.000 description 1
- JFPVXVDWJQMJEE-OCKHKDLRSA-N CO/N=C(\C(NC(C1SCC(COC(N)=O)=C(C(O)=O)N11)C1=O)=O)/c1ccc[o]1 Chemical compound CO/N=C(\C(NC(C1SCC(COC(N)=O)=C(C(O)=O)N11)C1=O)=O)/c1ccc[o]1 JFPVXVDWJQMJEE-OCKHKDLRSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 102000006635 beta-lactamase Human genes 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000021235 carbamoylation Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 101150061972 zur gene Proteins 0.000 description 1
Classifications
-
- 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
- C07D501/26—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group
- C07D501/34—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group with the 7-amino radical acylated by carboxylic acids containing hetero rings
Definitions
- the present invention is in the field of chemistry and more particularly the invention deals with the process for the purification of cefuroxime acid ⁇ (6R, 7R)-3- carbamoyloxymethyl-7-[(Z)-2-(fur-2-yl)-2-methoxy-iminoacetamido] ceph-3-em-4- carboxylic acid ⁇ of general formula (I).
- Cefuroxime acid is a key intermediate for the industrial synthesis of cefuroxime sodium (for the injection administration) and cefuroxime axetil (for the oral administration). These compounds have a valuable broad spebtrum and having activity against wide range of gram-positive and gram-negative microorganisms. Their effectiveness is advantageously combined with remarkable resistance to ⁇ -lactamases.
- Cefuroxime can be prepared by condensation of 3-hydroxymethyl-7-amino cephalosporanic acid with (fur-2-yl)-2-methoxyimino. acetic acid to produce (6R,7R)-7- [(Z)-2-(fur-2-yl)-2-methoxyiminoacetamido]-3-hydroxymethylceph-3-em-4-carboxylic acid followed by carbamoylation of resulting acid with isocyanate of formula RNCO wherein R is a labile substituent to get (6R,7R)-3-carbamoyloxymethyl-7-[(Z)-2-(fur-2 ⁇ yl)-2-methoxyimino acetamido] ceph-3-em-4-carboxylic acid (cefuroxime acid).
- An object of the present invention is to provide a simple and environment friendly process for the purification of cefuroxime acid of formula (I) with good yield, high purity and color absorbance of less than 0.1 at 410 nm.
- the present invention provides process for the process for the purification of cefuroxime acid ⁇ (6R, 7R)-3-carbamoyloxymethyl-7-[(Z)-2-(fur-2-yl)-2-methoxy- iminoacetamido] ceph-3-em-4-carboxylic acid ⁇ of general formula (I).
- the present invention provides a simple and environment friendly process for the preparation of cefuroxime acid of formula (I) with high purity and improved color.
- Cefuroxime acid with color absorbance of less than 0.1 at 410nm is useful for manufacturing of cefuroxime axetil having acceptable quality in terms of purity and color.
- the spray drying process for making amorphous cefuroxime axetil always result in the enhancement of color hence it is utmost important to control the color of cefuroxime acid to get acceptable quality of amorphous cefuroxime axetil.
- the acid product can easily be converted into the corresponding pharmaceutically acceptable salt or ester, preferably into cefuroxime salt and cefuroxime axetil, by using conventional techniques known to those skilled in the art.
- polar aprotic solvent is selected from the group of acetonitrile, dioxane, tetrahydrofuran, alcohol or acetone.
- Base used in this invention is selected from the group of alkali/alkaline earth metal hydroxides like sodium hydroxide, potassium hydroxide.
- dissolution is carried out in the temperature range of 0 to 5°C.
- the above solution is then charcoalised with activated carbon followed by filtration.
- the charcoalisation is carried out in the temperature range of 0 to 5 0 C.
- the acid used for adjusting pH from 1.5-2.5 is selected from the group of hydrochloric acid or sulphuric acid, more preferable pH to isolate the cefuroxime acid of formula (I) in pure form having color absorbance less than 0.1 at 410 nm and purity more than 99.0% in the range of 2.0 ⁇ 0.05 at a temperature in the range of 0 to 5 0 C .
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Abstract
The present invention relates to a process for the purification of cefuroxime acid {(6R,7R)-3-carbamoyloxymethyl-7-[(Z)-2-(fur-2-yl)-2-methoxy-iminoacetamido] ceph-3-em-4-carboxylic acid} of formula (I).
Description
"PURIFICATION OF CEFUROXIME ACID"
Field of the Invention: The present invention is in the field of chemistry and more particularly the invention deals with the process for the purification of cefuroxime acid {(6R, 7R)-3- carbamoyloxymethyl-7-[(Z)-2-(fur-2-yl)-2-methoxy-iminoacetamido] ceph-3-em-4- carboxylic acid} of general formula (I).
(I)
Background of the Invention:
Cefuroxime acid is a key intermediate for the industrial synthesis of cefuroxime sodium (for the injection administration) and cefuroxime axetil (for the oral administration). These compounds have a valuable broad spebtrum and having activity against wide range of gram-positive and gram-negative microorganisms. Their effectiveness is advantageously combined with remarkable resistance to β-lactamases.
Cefuroxime can be prepared by condensation of 3-hydroxymethyl-7-amino cephalosporanic acid with (fur-2-yl)-2-methoxyimino. acetic acid to produce (6R,7R)-7- [(Z)-2-(fur-2-yl)-2-methoxyiminoacetamido]-3-hydroxymethylceph-3-em-4-carboxylic acid followed by carbamoylation of resulting acid with isocyanate of formula RNCO wherein R is a labile substituent to get (6R,7R)-3-carbamoyloxymethyl-7-[(Z)-2-(fur-2~ yl)-2-methoxyimino acetamido] ceph-3-em-4-carboxylic acid (cefuroxime acid).
In prior art pure crystalline cefuroxime axetil is obtained by cefuroxime sodium from either 3-hydroxy cefuroxime or cefuroxime. Therefore, the said process involves an additional step of preparing sodium cefuroxime and therefore it is not economical.
If purification of cefuroxime axetil or cefuroxime sodium is done without purifying cefuroxime then the yield of the final product will be low. Purify the compound on penultimate stage is more economical rather than on the final stage.
Hence, there is unmet need to develop a simple and environment friendly process for the purification of cefuroxime acid, which is convenient to perform on a commercial scale, operationally safe and provide the product in pure form.
Objects of the Invention:
An object of the present invention is to provide a simple and environment friendly process for the purification of cefuroxime acid of formula (I) with good yield, high purity and color absorbance of less than 0.1 at 410 nm.
Summary of the Invention:
The present invention provides process for the process for the purification of cefuroxime acid {(6R, 7R)-3-carbamoyloxymethyl-7-[(Z)-2-(fur-2-yl)-2-methoxy- iminoacetamido] ceph-3-em-4-carboxylic acid} of general formula (I).
DETAILED DISCRIPTION OF THE INVENTION
Accordingly, the present invention provides a simple and environment friendly process for the preparation of cefuroxime acid of formula (I) with high purity and improved color. Cefuroxime acid with color absorbance of less than 0.1 at 410nm is useful for manufacturing of cefuroxime axetil having acceptable quality in terms of purity and color. The spray drying process for making amorphous cefuroxime axetil always result in the enhancement of color hence it is utmost important to control the color of cefuroxime acid to get acceptable quality of amorphous cefuroxime axetil.
The process for purification of cefuroxime acid of formula (I),
(I)
Which comprises the steps of:
(i) dissolving impure cefuroxime acid of formula (I) in a mixture of water and polar aprotic solvent, (ii) adjusting the pH of the mixture in the range 6.0 to 7.0 by adding a base to get a clear solution,
(iii) treating the solution with activated charcoal followed by filtration, (iv) adjusting the pH of the filtrate to 3.5-3.6 by adding dilute acid and; (v) isolating the precipitated product by adjusting pH 1.5-2.5 by adding dilute acid at a temperature range 0 to 50C.
Moreover, the acid product can easily be converted into the corresponding pharmaceutically acceptable salt or ester, preferably into cefuroxime salt and cefuroxime axetil, by using conventional techniques known to those skilled in the art.
For purposes of this invention, polar aprotic solvent is selected from the group of acetonitrile, dioxane, tetrahydrofuran, alcohol or acetone.
Base used in this invention is selected from the group of alkali/alkaline earth metal hydroxides like sodium hydroxide, potassium hydroxide.
Preferably, dissolution is carried out in the temperature range of 0 to 5°C. The above solution is then charcoalised with activated carbon followed by filtration. Preferably, the charcoalisation is carried out in the temperature range of 0 to 50C.
Finally, the acid used for adjusting pH from 1.5-2.5 is selected from the group of hydrochloric acid or sulphuric acid, more preferable pH to isolate the cefuroxime acid of formula (I) in pure form having color absorbance less than 0.1 at 410 nm and purity more than 99.0% in the range of 2.0±0.05 at a temperature in the range of 0 to 50C .
The invention is illustrated by the following examples which are only meant to illustrate the invention and not act as limitations. All embodiments apparent to a process their in the art are deemed to fall within the scope of the present invention.
Examples
Example- 1
Crude cefuroxime acid [(10.0 g), purity: 98.73%, Color absorbance: 2.263] was added to the mixture of water (130 ml) and ACN (30 ml) at 25-300C. The pH of the solution was adjusted to 6.0 to 7.0 by adding 10 % sodium hydroxide solution and was stirred for 60 minutes at 0 to 5°C to get the clear solution. Activated charcoal was added and stirred for 30 minutes at 0 to 50C. The solution was filtered and washed with 10 ml of water. The pH of the filtrate was adjusted to 3.5 to 3.6 by adding 5% HCl and was stirred for 30 minutes at 0 to 50C. Finally, the. pH was adjusted to 1.5 to 2.1 by adding 5% HCl solution and was stirred for 60 minutes at 0 to 5°C. The product was filtered and washed with a mixture of ACN and water. The product was dried to get cefuroxime acid (6.0 g) in pure form. HPLC purity: 99.50 %, Color absorbance: 0.04.
Example 2-9
The reaction was conducted in the similar manner as explained in example 1 by using different solvents. Results are given in Table 1. '
Table: 1
Abbreviations
ACN : Acetonitrile
HCl : Hydrochloric acid
IPA : Isopropyl alcohol
THF : Tetrahydrofuran
MDC : Dichloromethane
Claims
We Claim:
1) A process for the purification of cefuroxime acid of general formula (I)
comprising the steps of:
(i) dissolving impure cefuroxime acid of formula (I) in a mixture of water and polar aprotic solvent (ii) adjusting the pH of the mixture in the range of 6.0 to 7.0 by adding a base to get a clear solution,
(ii) treating the solution with activated charcoal followed by filtration, (iii) adjusting the pH of the filtrate to 3.5 to 3.6 by adding dilute acid and; (iv) isolating the precipitated product by adjusting pH 1.5-2.5 by adding dilute acid at a temperature range 0 to 50C.
2) The process as claimed in claim 1, wherein the polar aprotic solvent used in step (i) is selected from the group of acetonitrile, Tetrahydrofuran, acetone, dioxane or mixture thereof.
3) The process as claimed in claim 2, wherein the preferred polar aprotic solvent is acetonitrile.
4) The process as claimed in claim I5 wherein said base used in step (ii) is selected from alkali or alkaline earth metal hydroxides like sodium hydroxide, potassium hydroxide.
5) The process as claimed in claim 4, wherein the preferred base is sodium hydroxide. • .
6) The process as claimed in claim 1, wherein the acid used in step (iv)is selected from the group of hydrochloric acid or sulphuric acid.
7) The process as claimed in claim 1, wherein the said pure cefuroxime acid having the color absorbance less than 0.1 at 410 nm. 8) Cefuroxime acid having the color absorbance less than 0.1 at 410 nm.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN934/DEL/2007 | 2007-04-27 | ||
| IN934DE2007 | 2007-04-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2008132574A1 true WO2008132574A1 (en) | 2008-11-06 |
Family
ID=39925241
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/IB2008/000983 WO2008132574A1 (en) | 2007-04-27 | 2008-04-22 | Purification of cefuroxime acid |
Country Status (1)
| Country | Link |
|---|---|
| WO (1) | WO2008132574A1 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102295653A (en) * | 2010-06-28 | 2011-12-28 | 广州白云山制药股份有限公司广州白云山化学制药厂 | One-step recovery and preparation method of cefuroxime sodium |
| CN110857307A (en) * | 2018-08-24 | 2020-03-03 | 浙江长典医药有限公司 | Preparation method of cefuroxime sodium for injection |
| CN112480146A (en) * | 2020-10-30 | 2021-03-12 | 浙江惠迪森药业有限公司 | Cefuroxime acid mixed solvate, crystal form and preparation method |
| CN118994198A (en) * | 2024-10-22 | 2024-11-22 | 山东信立泰药业有限公司 | Recycling method of cefuroxime sodium mother liquor |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000053609A1 (en) * | 1999-03-09 | 2000-09-14 | Ranbaxy Laboratories Limited | Process for the preparation of cefuroxime |
| WO2004050663A2 (en) * | 2002-12-05 | 2004-06-17 | Orchid Chemicals & Pharmaceuticals Ltd | An improved process for the preparation of cefuroxime sodium |
-
2008
- 2008-04-22 WO PCT/IB2008/000983 patent/WO2008132574A1/en active Application Filing
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000053609A1 (en) * | 1999-03-09 | 2000-09-14 | Ranbaxy Laboratories Limited | Process for the preparation of cefuroxime |
| WO2004050663A2 (en) * | 2002-12-05 | 2004-06-17 | Orchid Chemicals & Pharmaceuticals Ltd | An improved process for the preparation of cefuroxime sodium |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102295653A (en) * | 2010-06-28 | 2011-12-28 | 广州白云山制药股份有限公司广州白云山化学制药厂 | One-step recovery and preparation method of cefuroxime sodium |
| CN110857307A (en) * | 2018-08-24 | 2020-03-03 | 浙江长典医药有限公司 | Preparation method of cefuroxime sodium for injection |
| CN112480146A (en) * | 2020-10-30 | 2021-03-12 | 浙江惠迪森药业有限公司 | Cefuroxime acid mixed solvate, crystal form and preparation method |
| CN118994198A (en) * | 2024-10-22 | 2024-11-22 | 山东信立泰药业有限公司 | Recycling method of cefuroxime sodium mother liquor |
| CN118994198B (en) * | 2024-10-22 | 2025-01-10 | 山东信立泰药业有限公司 | Recycling method of cefuroxime sodium mother liquor |
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