WO2023272962A1 - Procédé de détection de petites impuretés polaires dans un médicament en vrac de mésylate de pazufloxacine - Google Patents
Procédé de détection de petites impuretés polaires dans un médicament en vrac de mésylate de pazufloxacine Download PDFInfo
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- WO2023272962A1 WO2023272962A1 PCT/CN2021/119262 CN2021119262W WO2023272962A1 WO 2023272962 A1 WO2023272962 A1 WO 2023272962A1 CN 2021119262 W CN2021119262 W CN 2021119262W WO 2023272962 A1 WO2023272962 A1 WO 2023272962A1
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- WIPO (PCT)
- Prior art keywords
- solution
- pazufloxacin mesylate
- pazufloxacin
- mesylate
- performance liquid
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- XAGMUUZPGZWTRP-ZETCQYMHSA-N LSM-5745 Chemical compound C([C@@H](N1C2=C(C(C(C(O)=O)=C1)=O)C=C1F)C)OC2=C1C1(N)CC1 XAGMUUZPGZWTRP-ZETCQYMHSA-N 0.000 title claims abstract description 66
- 229960002625 pazufloxacin Drugs 0.000 title claims abstract description 66
- 229940079593 drug Drugs 0.000 title claims abstract description 41
- 239000003814 drug Substances 0.000 title claims abstract description 41
- 239000012535 impurity Substances 0.000 title claims abstract description 23
- 238000000034 method Methods 0.000 title claims abstract description 23
- 238000004128 high performance liquid chromatography Methods 0.000 claims abstract description 31
- 238000001514 detection method Methods 0.000 claims abstract description 27
- 230000014759 maintenance of location Effects 0.000 claims abstract description 20
- 239000007788 liquid Substances 0.000 claims abstract description 10
- 238000012360 testing method Methods 0.000 claims abstract description 10
- KQYREKISXCBRQB-UHFFFAOYSA-N n,n-diethylethanamine;methanesulfonic acid Chemical compound CS(O)(=O)=O.CCN(CC)CC KQYREKISXCBRQB-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000000243 solution Substances 0.000 claims description 28
- 239000012085 test solution Substances 0.000 claims description 20
- KFGJICJPSZZEEP-UHFFFAOYSA-L dipotassium;hydrogen phosphate;hydrate Chemical compound O.[K+].[K+].OP([O-])([O-])=O KFGJICJPSZZEEP-UHFFFAOYSA-L 0.000 claims description 7
- 238000001228 spectrum Methods 0.000 claims description 5
- 238000002347 injection Methods 0.000 claims description 4
- 239000007924 injection Substances 0.000 claims description 4
- 230000005526 G1 to G0 transition Effects 0.000 claims description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 3
- YTJSFYQNRXLOIC-UHFFFAOYSA-N octadecylsilane Chemical group CCCCCCCCCCCCCCCCCC[SiH3] YTJSFYQNRXLOIC-UHFFFAOYSA-N 0.000 claims description 3
- 230000035945 sensitivity Effects 0.000 claims description 3
- 239000000741 silica gel Substances 0.000 claims description 3
- 229910002027 silica gel Inorganic materials 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 5
- 238000003908 quality control method Methods 0.000 abstract description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 abstract 1
- 239000012488 sample solution Substances 0.000 abstract 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 230000015556 catabolic process Effects 0.000 description 11
- 238000006731 degradation reaction Methods 0.000 description 11
- 239000002253 acid Substances 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000003513 alkali Substances 0.000 description 5
- 239000007857 degradation product Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000001782 photodegradation Methods 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 239000008186 active pharmaceutical agent Substances 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- 208000004429 Bacillary Dysentery Diseases 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- 206010017915 Gastroenteritis shigella Diseases 0.000 description 1
- 208000032376 Lung infection Diseases 0.000 description 1
- 206010062255 Soft tissue infection Diseases 0.000 description 1
- 229940124350 antibacterial drug Drugs 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940124307 fluoroquinolone Drugs 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 201000005113 shigellosis Diseases 0.000 description 1
- 206010040872 skin infection Diseases 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
Images
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/26—Conditioning of the fluid carrier; Flow patterns
- G01N30/28—Control of physical parameters of the fluid carrier
- G01N30/34—Control of physical parameters of the fluid carrier of fluid composition, e.g. gradient
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/62—Detectors specially adapted therefor
- G01N30/74—Optical detectors
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/86—Signal analysis
- G01N30/8624—Detection of slopes or peaks; baseline correction
- G01N30/8631—Peaks
- G01N30/8634—Peak quality criteria
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/88—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/88—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86
- G01N2030/8809—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86 analysis specially adapted for the sample
- G01N2030/8872—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86 analysis specially adapted for the sample impurities
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Definitions
- the application relates to the field of quality control of the raw materials of pazufloxacin mesylate, in particular to a detection method for small polar impurities in the raw materials of pazufloxacin mesylate.
- Pazufloxacin mesylate is a new type of fluoroquinolone antibacterial drug developed by Japan. It is the mesylate salt of Pazufloxacin. It has the characteristics of broad antibacterial spectrum, high antibacterial activity, small side effects and good tolerance. It is clinically used to treat Gram-positive and negative bacterial infections, such as bronchial and lung infections, bacillary dysentery, urinary system, skin and soft tissue infections.
- Pazufloxacin mesylate API may produce some degradation products after exposure to light, oxidation, high temperature, and acid and alkali during storage, transportation and use. These degradation products may affect the efficacy and even safety of the drug. will have an impact, therefore, it is necessary to detect these degradation products.
- HPLC high performance liquid chromatography
- the inventor finds after studying a large amount of HPLC detection methods, the flow that these HPLC detection methods adopts is relative to the impurity of small polarity, especially the impurity that retention time is greater than main drug pazufloxacin mesylate characteristic peak, and cannot be detected effectively.
- These small polar impurities may be derived from some degradation products of Pazufloxacin Mesylate bulk drug due to light, oxidation, high temperature, and acid and alkali during storage, transportation and use. The curative effect and even the safety of the drug may be affected. Therefore, a comprehensive and accurate detection of these small polar impurities is very necessary for the quality control of the drug.
- the invention provides a method for detecting small polar impurities in the raw drug of pazufloxacin mesylate, so as to control the quality of the raw drug of pazufloxacin mesylate more comprehensively and accurately.
- a method for detecting small polar impurities in the bulk drug of pazufloxacin mesylate which is detected by high performance liquid chromatography, and the mobile phase is acetonitrile-10% trimethanesulfonate with a volume ratio of 45:10:7:138 Ethylamine solution-1.0mol/L dipotassium hydrogen phosphate-water;
- the method comprises the steps of:
- the peak area of the impurity whose retention time is greater than the characteristic peak of pazufloxacin mesylate in the spectrum of the test solution obtained is compared with the characteristic peak area of pazufloxacin mesylate in the spectrum of the test solution to determine The content of this impurity relative to pazufloxacin mesylate.
- the test solution is diluted 100 times to obtain the control solution.
- the concentration of the bulk drug of pazufloxacin mesylate in the test solution is 0.3 mg/ml.
- the injection volume of the high performance liquid chromatograph is 20 ⁇ l.
- the chromatographic conditions of high performance liquid chromatography also include:
- the resolution of high performance liquid chromatography is 1.6.
- the number of theoretical plates of high-performance liquid chromatography calculated based on the characteristic peak of pazufloxacin mesylate should not be less than 2000.
- described method before taking need testing solution and control solution respectively and injecting high-performance liquid chromatograph, described method also comprises:
- the detection method of the present application adopts HPLC to detect the raw material drug of pazufloxacin mesylate, and through the mobile phase of specific proportioning, the retention time can be effectively reduced to 7 times of that of pazufloxacin mesylate. Small polar impurities larger than the characteristic peaks of pazufloxacin mesylate were detected. Therefore, the quality control of the Pazufloxacin Mesylate API can be realized more accurately and scientifically.
- Fig. 1A is the HPLC chromatogram that adopts mobile phase 1 to detect the bulk drug of pazufloxacin mesylate in embodiment 1;
- Fig. 1B is the HPLC chromatogram that adopts mobile phase 2 to detect the bulk drug of pazufloxacin mesylate in Example 1;
- Fig. 1 C is the HPLC chromatogram that adopts mobile phase 3 to detect the bulk drug of pazufloxacin mesylate in Example 1;
- Fig. 1D is the HPLC chromatogram that adopts mobile phase 4 to detect the bulk drug of pazufloxacin mesylate in Example 1;
- Fig. 2 is the HPLC chromatogram of the pazufloxacin mesylate crude drug after photodegradation in embodiment 2;
- Fig. 3 is the HPLC chromatogram of the pazufloxacin mesylate crude drug after acid degradation in embodiment 3;
- Fig. 4 is the HPLC chromatogram of the bulk drug of pazufloxacin mesylate after alkaline degradation in Example 4.
- Embodiment 1 is used to detect the screening of the mobile phase of small polar impurity
- the mobile phase pazufloxacin mesylate raw materials in Table 1 below were used for detection.
- mobile phase 1 Acetonitrile-10% triethylamine methanesulfonate-1M dipotassium hydrogen phosphate-water (30:10:7:170) mobile phase 2 Acetonitrile-10% triethylamine methanesulfonate-1M dipotassium hydrogen phosphate-water (30:10:7:153) mobile phase 3 Acetonitrile-10% triethylamine methanesulfonate-1M dipotassium hydrogen phosphate-water (45:10:7:138) mobile phase 4 Acetonitrile-10% triethylamine methanesulfonate-1M dipotassium hydrogen phosphate-water (70:10:7:113)
- Injection volume 20 ⁇ l.
- the detection steps are as follows:
- test solution take 30 mg of pazufloxacin mesylate crude drug, accurately weigh it, put it in a 100ml measuring bottle, add mobile phase to dissolve and dilute to the mark, shake well, and use it as the test solution.
- the application adopts the mobile phase of acetonitrile-10% triethylamine methanesulfonate solution-1.0mol/L dipotassium hydrogen phosphate-water with a volume ratio of 45:10:7:138.
- small polar impurities can be detected comprehensively and accurately.
- the detection steps are as follows:
- the small polarity produced by the degradation can be reduced by using the mobile phase provided by the application within the retention time of the characteristic peak of pazufloxacin mesylate 7 times. Impurities are detected comprehensively and accurately.
- the detection steps are as follows:
- test solution for acid degradation take 30 mg of pazufloxacin mesylate crude drug, place it in a 50 ml measuring bottle, add 25 ml of 1.0 mol/L hydrochloric acid and heat it in a boiling water bath for 12 hours in the dark, and add 1.0 mol/L sodium hydroxide was diluted and neutralized to the mark as the test solution.
- the detection steps are as follows:
- the low polarity produced by the degradation can be reduced by using the mobile phase provided by the application within the retention time of 7 times the characteristic peak of pazufloxacin mesylate. Impurities are detected comprehensively and accurately.
- the detection steps are as follows:
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- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Engineering & Computer Science (AREA)
- Quality & Reliability (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
L'invention concerne un procédé de détection de petites impuretés polaires dans un médicament en vrac de mésylate de pazufloxacine, la détection étant réalisée par la mise en œuvre d'un procédé de chromatographie liquide à haute performance (HPLC) ; et une phase mobile comprend de l'acétonitrile, une solution de mésylate de triéthylamine à 10 %, un hydrogénophosphate dipotassique à 1,0 mol/L, et de l'eau, dans un rapport volumique de 45 : 10 : 7 : 138. Le procédé selon l'invention consiste : à injecter respectivement une solution d'échantillon de test et une solution témoin dans un chromatographe liquide à haute performance, et à enregistrer un chromatogramme jusqu'à 7 fois le temps de rétention d'un pic caractéristique du mésylate de pazufloxacine. Selon le procédé, un médicament en vrac de mésylate de pazufloxacine est soumis à une détection par HPLC, et de petites impuretés polaires avec un temps de rétention plus long que celui d'un pic caractéristique du mésylate de pazufloxacine peuvent être efficacement détectées durant 7 fois le temps de rétention du mésylate de pazufloxacine au moyen d'une phase mobile ayant un rapport spécifique. Ainsi, le contrôle qualité d'un médicament en vrac de mésylate de pazufloxacine peut être réalisé de façon plus précise et plus scientifique.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110738109.5A CN113702517A (zh) | 2021-06-30 | 2021-06-30 | 甲磺酸帕珠沙星原料药中小极性杂质的检测方法 |
| CN202110738109.5 | 2021-06-30 |
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| Publication Number | Publication Date |
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| WO2023272962A1 true WO2023272962A1 (fr) | 2023-01-05 |
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| PCT/CN2021/119262 WO2023272962A1 (fr) | 2021-06-30 | 2021-09-18 | Procédé de détection de petites impuretés polaires dans un médicament en vrac de mésylate de pazufloxacine |
Country Status (2)
| Country | Link |
|---|---|
| CN (1) | CN113702517A (fr) |
| WO (1) | WO2023272962A1 (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115919761A (zh) * | 2023-01-29 | 2023-04-07 | 浙江莎普爱思药业股份有限公司 | 一种甲磺酸帕珠沙星液体制剂及其制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114354794A (zh) * | 2021-12-29 | 2022-04-15 | 四川美大康佳乐药业有限公司 | 一种甲磺酸帕珠沙星注射剂的质量控制方法 |
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| CN102295652A (zh) * | 2011-06-27 | 2011-12-28 | 辽宁海神联盛制药有限公司 | 一种甲磺酸帕珠沙星合成工艺的改进方法 |
| CN105287371A (zh) * | 2015-11-24 | 2016-02-03 | 河北智同生物制药有限公司 | 一种甲磺酸帕珠沙星注射液组合物及其制备方法 |
| CN105388221A (zh) * | 2015-10-13 | 2016-03-09 | 康普药业股份有限公司 | 一种甲磺酸帕珠沙星质量检测方法 |
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| CN113640403A (zh) * | 2021-07-12 | 2021-11-12 | 海南海神同洲制药有限公司 | 甲磺酸帕珠沙星原料药的含量检测方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101897666B (zh) * | 2009-05-31 | 2013-06-12 | 北京四环科宝制药有限公司 | 甲磺酸帕珠沙星注射制剂及其检测方法 |
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- 2021-06-30 CN CN202110738109.5A patent/CN113702517A/zh active Pending
- 2021-09-18 WO PCT/CN2021/119262 patent/WO2023272962A1/fr active Application Filing
Patent Citations (5)
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| CN102295652A (zh) * | 2011-06-27 | 2011-12-28 | 辽宁海神联盛制药有限公司 | 一种甲磺酸帕珠沙星合成工艺的改进方法 |
| CN105388221A (zh) * | 2015-10-13 | 2016-03-09 | 康普药业股份有限公司 | 一种甲磺酸帕珠沙星质量检测方法 |
| CN105287371A (zh) * | 2015-11-24 | 2016-02-03 | 河北智同生物制药有限公司 | 一种甲磺酸帕珠沙星注射液组合物及其制备方法 |
| CN113624859A (zh) * | 2021-06-30 | 2021-11-09 | 海南海神同洲制药有限公司 | 采用hplc检测甲磺酸帕珠沙星原料药中有关物质的方法 |
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Non-Patent Citations (1)
| Title |
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| HU XIN, YAN XIAOYAN, CAO GUOYING, HE XIAORONG: "Determination of pazufloxacin mesilate and its related substances by RP-HPLC", CHINESE JOURNAL OF NEW DRUGS, GAI-KAN BIANJIBU, BEIJING, CN, vol. 11, no. 11, 31 December 2002 (2002-12-31), CN , pages 862 - 865, XP093017941, ISSN: 1003-3734 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115919761A (zh) * | 2023-01-29 | 2023-04-07 | 浙江莎普爱思药业股份有限公司 | 一种甲磺酸帕珠沙星液体制剂及其制备方法 |
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