CN1752749A - Method of detecting ornidazole optical antipode by high efficient liquid chromatography - Google Patents
Method of detecting ornidazole optical antipode by high efficient liquid chromatography Download PDFInfo
- Publication number
- CN1752749A CN1752749A CN 200510005945 CN200510005945A CN1752749A CN 1752749 A CN1752749 A CN 1752749A CN 200510005945 CN200510005945 CN 200510005945 CN 200510005945 A CN200510005945 A CN 200510005945A CN 1752749 A CN1752749 A CN 1752749A
- Authority
- CN
- China
- Prior art keywords
- ornidazole
- butyl ether
- methyl tert
- solution
- isopropyl alcohol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Landscapes
- Treatment Of Liquids With Adsorbents In General (AREA)
- Investigating Or Analysing Materials By Optical Means (AREA)
Abstract
The present invention provides a method for detecting orinidazol optical enantiomer by utilizing PHLC. It is characterized by that (1) chromatographic condition: its chromatographic column adopts chiral column, using cellulose esters as stationary phase, using n-hexane-methyl t-butyl ether-isopropanol-glacial acetic acid as mobile phase, and the detection wavelength is 280nm-340nm; (2) adopting organic solrent to prepare sample solution containing orinidazole raceme 0.05-0.5mg/ml; and (3) determining and recording chromatogram.
Description
Technical field
The present invention relates to detect the method for ornidazole optical enantiomorph, say so more specifically and detect in the Ornidazole production run or left and right method of revolving Ornidazole in the Ornidazole product by high performance liquid chromatography.
Background technology
Ornidazole (Ornidazole, CAS 16773-42-5) is a nitro imidazole derivatives, its chemistry 1-(3-chloro-2-hydroxypropyl) by name-2-methyl-5-nitro imidazoles, molecular formula: C
7H
10ClN
3O
3, molecular weight: 219.6, be the medicine that a kind of powerful anaerobe resistant and antiprotozoan infect.The anti-microbial effect of Ornidazole is to be reduced into amino by the nitro in its molecule in oxygen-free environment, or interacts by the formation and the cell component of free radical, thereby causes the death of microorganism.The method that a lot of racemies separate by high performance liquid chromatography is known, but factors such as moving phase, solvent, column temperature, chromatographic column have a significant impact for split result or are not suitable for the target raceme.
Summary of the invention
The purpose of this invention is to provide the method that detects gained ornidazole optical enantiomorph in Ornidazole raceme chirality is synthetic by high performance liquid chromatography, with the purity of control synthetic sample.
It is that the chiral column of stationary phase splits that the present invention adopts cellulose esters, a hydroxyl and a chloromethyl are arranged on the Ornidazole asymmetric carbon atom, and the formation of hole in the cellulose esters class formation and passage and enantio-selectivity the enantiomorph inclusion compound, thereby reach separation.
Moving phase is revolved the Ornidazole degree of separation and peak shape all has a significant impact to left and right in the experimental result, grope through inventor's experiment, determine with normal hexane-methyl tert-butyl ether-isopropyl alcohol-glacial acetic acid (75～100: 2～15: 0.1～8: 0.1～1.5, be preferably 85～95: 6～10: 0.5～3: 0.2～0.8, more preferably 90: 8: 2: be that the moving phase effect is fine 0.5).Wherein add methyl tert-butyl ether and can improve the left and right Ornidazole degree of separation of revolving, glacial acetic acid can improve peak shape.
Choice of Solvent is relevant with the left and right Ornidazole degree of separation of revolving.Determining to adopt n-propanol, isopropyl alcohol, ethanol, normal butyl alcohol, methyl alcohol or methyl tert-butyl ether to use solvent as dissolving through testing, preferably is solvent with the methyl tert-butyl ether.
It is provided by the invention that to detect the actual conditions of left and right method of revolving Ornidazole by high performance liquid chromatography as follows:
1. chromatographic condition: the chromatographic column adopting cellulose esters is the chiral column of stationary phase; Moving phase be normal hexane-methyl tert-butyl ether-isopropyl alcohol-glacial acetic acid (75～100: 2～15: 0.1～8: 0.1～1.5, be preferably 85～95: 6～10: 0.5～3: 0.2～0.8, more preferably 90: 8: 2: 0.5); The detection wavelength is 280nm～340nm (being preferably 300nm～320nm, more preferably about 310nm); Column temperature is 20～45 ℃ (being preferably 35～45 ℃, more preferably 40 ℃); Flow rate of mobile phase is 0.5～2.0ml/min (being preferably 0.8-1.2ml/min, more preferably about 1.0ml/min).
2. the configuration of sample solution: adopt organic solvent (to be preferably selected from n-propanol, isopropyl alcohol, ethanol, normal butyl alcohol, methyl alcohol or methyl tert-butyl ether, methyl tert-butyl ether more preferably), sample ligand is made as the solution that contains Ornidazole raceme 0.05～0.5mg/ml (preferred 0.1～0.3mg/ml, more preferably 0.2mg/ml).
3. measure: solution is injected high performance liquid chromatograph, the record chromatogram, and analyze.
Adopt this chromatographic condition to measure that the left and right Ornidazole degree of separation of revolving can reach 1.5～2.3 in Ornidazole raceme, meet the Chinese Pharmacopoeia requirement.This chromatographic condition can be used for the quantitative of ornidazole optical enantiomorph simultaneously.
Description of drawings
Fig. 1: the condition according to embodiment 1 is separated the left and right high-efficient liquid phase chromatogram that revolves Ornidazole.
Fig. 2: the condition according to embodiment 2 is separated the left and right high-efficient liquid phase chromatogram that revolves Ornidazole.
Embodiment
Embodiment 1.
Instrument: SHIMADZU LC-10AT high performance liquid chromatograph, SPD-10A UV-detector, HT-230A column oven;
Chromatographic column: Daicel Chralcel OB-H chromatographic column (0.46 * 25cm, 5 μ m);
Moving phase: normal hexane-methyl tert-butyl ether-isopropyl alcohol-glacial acetic acid (90: 8: 2: 0.5)
Column temperature: 40 ℃;
Flow velocity: 1.0ml/min;
Detect wavelength: 310nm.
The configuration of location solution 1: it is an amount of that precision takes by weighing laevo-ornidazole, with methyl tert-butyl ether dissolving and be diluted to 0.1mg/ml;
The configuration of location solution 2: it is an amount of that precision takes by weighing (r)-ornidazole, with methyl tert-butyl ether dissolving and be diluted to 0.1mg/ml;
The configuration of sample solution: it is an amount of that precision takes by weighing the Ornidazole raceme, with methyl tert-butyl ether dissolving and be diluted to 0.2mg/ml;
Measure: respectively get location solution 1, location solution 2, sample solution 20 μ l and injects high performance liquid chromatograph, write down chromatogram, spectrogram is seen Fig. 1.The left and right Ornidazole degree of separation of revolving is 2.3 in the Ornidazole raceme.Wherein laevo-ornidazole content is 44% in the Ornidazole raceme, and (r)-ornidazole content is 56%.
Embodiment 2.
Instrument: SHIMADZU LC-10AT high performance liquid chromatograph, SPD-10A UV-detector, HT-230A column oven;
Chromatographic column: Hibar RT Cellulose Triacetate chromatographic column (0.46 * 25cm, 10 μ m);
Moving phase: normal hexane-methyl tert-butyl ether-isopropyl alcohol-glacial acetic acid (90: 8: 5: 0.6)
Column temperature: 40 ℃;
Flow velocity: 1.5ml/min;
Detect wavelength: 300nm.
The configuration of location solution 1: it is an amount of that precision takes by weighing laevo-ornidazole, with dissolve with ethanol and be diluted to 0.1mg/ml;
The configuration of location solution 2: it is an amount of that precision takes by weighing (r)-ornidazole, with dissolve with ethanol and be diluted to 0.1mg/ml;
The configuration of sample solution: it is an amount of that precision takes by weighing the Ornidazole raceme, with dissolve with ethanol and be diluted to 0.2mg/ml;
Measure: respectively get location solution 1, location solution 2, sample solution 20 μ l and injects high performance liquid chromatograph, write down chromatogram, collection of illustrative plates is seen Fig. 2.The left and right Ornidazole degree of separation of revolving is 2.0 in the Ornidazole raceme.Wherein laevo-ornidazole content is 45% in the Ornidazole raceme, and (r)-ornidazole content is 55%.
Claims (7)
1. detect the method for ornidazole optical enantiomorph by high performance liquid chromatography, specific as follows:
1) chromatographic condition: the chromatographic column adopting cellulose esters is the chiral column of stationary phase; Moving phase is normal hexane-methyl tert-butyl ether-isopropyl alcohol-glacial acetic acid (75～100: 2～15: 0.1～8: 0.1～1.5); The detection wavelength is 280nm～340nm; Column temperature is 20～45 ℃; Flow rate of mobile phase is 0.5～2.0ml/min;
2) configuration of sample solution: adopt organic solvent that sample ligand is made for the solution that contains Ornidazole raceme 0.05～0.5mg/ml, described organic solvent is selected from n-propanol, isopropyl alcohol, ethanol, normal butyl alcohol, methyl alcohol and methyl tert-butyl ether;
3) measure: solution is injected high performance liquid chromatograph, and the record chromatogram is also analyzed.
2. method according to claim 1, it is characterized in that described moving phase is that (85～95: 6～10: 0.5～3: 0.2～0.8), more preferably normal hexane-methyl tert-butyl ether-isopropyl alcohol-glacial acetic acid is (90: 8: 2: 0.5) for normal hexane-methyl tert-butyl ether-isopropyl alcohol-glacial acetic acid.
3. method according to claim 1 is characterized in that detecting wavelength and is preferably 300nm～320nm, more preferably 310nm.
4. method according to claim 1 is characterized in that column temperature is preferably 35～45 ℃, more preferably 40 ℃.
5. method according to claim 1 is characterized in that flow rate of mobile phase is preferably 0.8～1.2ml/min, more preferably 1.0ml/min.
6. according to each described method of claim 1-5, it is characterized in that the organic solvent that adopts in the configuration of sample solution is a methyl tert-butyl ether.
7. according to each described method of claim 1-5, it is characterized in that sample solution is formulated as and preferably contain Ornidazole raceme 0.1～0.3mg/ml, the more preferably solution of 0.2mg/ml.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100059453A CN100339707C (en) | 2005-02-01 | 2005-02-01 | Method of detecting ornidazole optical antipode by high efficient liquid chromatography |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100059453A CN100339707C (en) | 2005-02-01 | 2005-02-01 | Method of detecting ornidazole optical antipode by high efficient liquid chromatography |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1752749A true CN1752749A (en) | 2006-03-29 |
| CN100339707C CN100339707C (en) | 2007-09-26 |
Family
ID=36679688
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2005100059453A Active CN100339707C (en) | 2005-02-01 | 2005-02-01 | Method of detecting ornidazole optical antipode by high efficient liquid chromatography |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN100339707C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107917979A (en) * | 2016-10-11 | 2018-04-17 | 陕西合成药业股份有限公司 | A kind of HPLC methods for separating analysis l-ornidazole isomers |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1258003A (en) * | 1999-12-18 | 2000-06-28 | 中国科学院兰州化学物理研究所 | Liquid-phase chromatographic method for separating antimer of trimebutine |
| CN1134661C (en) * | 2000-03-09 | 2004-01-14 | 中国科学院山西煤炭化学研究所 | Method for analyzing 1,3-diaminosulfourea by using high-performance liquid-phase chromatography |
| US20040033968A1 (en) * | 2002-08-16 | 2004-02-19 | Lin Shun Y. | Optimal volume of intra-vaginal semisolid dosage forms for treating vaginal infections |
-
2005
- 2005-02-01 CN CNB2005100059453A patent/CN100339707C/en active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107917979A (en) * | 2016-10-11 | 2018-04-17 | 陕西合成药业股份有限公司 | A kind of HPLC methods for separating analysis l-ornidazole isomers |
Also Published As
| Publication number | Publication date |
|---|---|
| CN100339707C (en) | 2007-09-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Zhang et al. | Chiral separation of pharmaceuticals by high performance liquid chromatography | |
| Cirilli et al. | High-performance liquid chromatography enantioseparation of proton pump inhibitors using the immobilized amylose-based Chiralpak IA chiral stationary phase in normal-phase, polar organic and reversed-phase conditions | |
| Kumari Rayala et al. | Advances and challenges in the pharmacokinetics and bioanalysis of chiral drugs | |
| Ren et al. | Use of gamithromycin as a chiral selector in capillary electrophoresis | |
| Jang et al. | Doxycycline as a new chiral selector in capillary electrophoresis | |
| Badaloni et al. | Extending the use of “inverted chirality columns approach” for enantiomeric excess determination in absence of reference samples: application to a water-soluble camptothecin derivative | |
| Ding et al. | Enantioseparation of chiral mandelic acid derivatives by supercritical fluid chromatography | |
| Xu et al. | Synthesis, application and molecular modeling study of ionic liquid functionalized lactobionic acid, 3-methyl-1-(3-sulfopropyl)-1 H-imidazol-3-ium lactobionate, as a chiral selector in capillary electrophoresis | |
| CN114544809B (en) | HPLC (high performance liquid chromatography) detection method for chiral purity of arformoterol intermediate and enantiomer thereof | |
| CN104764825A (en) | Method for separating and detecting enantiomer of ezetimibe key intermediate | |
| Naidong et al. | Development and validation of a high-performance liquid chromatographic method for the quantitation of warfarin enantiomers in human plasma | |
| CN100339707C (en) | Method of detecting ornidazole optical antipode by high efficient liquid chromatography | |
| Rosetti et al. | Simultaneous enantio-and diastereo-selective high-performance liquid chromatography separation of paroxetine on an immobilized amylose-based chiral stationary phase under green reversed-phase conditions | |
| König | Enantioselective gas chromatography | |
| Zhang et al. | Analytical and preparative potential of immobilized polysaccharide-derived chiral stationary phases | |
| Zhou et al. | Chromatographic evaluation of perphenylcarbamoylated β-cyclodextrin bonded stationary phase for micro-high performance liquid chromatography and pressurized capillary electrochromatography | |
| Sun et al. | Enantioseparation and determination of alminoprofen in rat plasma and its application to a stereoselective pharmacokinetic study | |
| CN101881755B (en) | Method for detecting esmolol hydrochlorid optical isomer by high efficiency liquid chromatography | |
| CN103113211A (en) | Splitting method for racemic 2-benzene propanoic acid | |
| CN112630313A (en) | High performance liquid phase resolution method of (S) -3-hydroxytetrahydrofuran enantiomer | |
| Soukup et al. | The use of cyclodextrin-based LC stationary phases for the separation of chiral dihydrobenzofuran derivatives | |
| CN114544810A (en) | HPLC detection method for chiral purity of paluvird starting material and enantiomer thereof | |
| CN101858892B (en) | Method for detecting landiolol hydrochloride optical isomers by high efficiency liquid chromatography | |
| Ficarra et al. | Direct separation of the enantiomers of reboxetine by liquid chromatography on different cellulose-and amylose-based chiral stationary phases | |
| CN108362789B (en) | High performance liquid chromatography detection method for abamectin sodium optical isomer |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| EE01 | Entry into force of recordation of patent licensing contract |
Application publication date: 20060329 Assignee: Yang Yifang Assignor: Nanjing Sanhome Pharmaceutical Co., Ltd. Contract record no.: 2013320000797 Denomination of invention: Method of detecting ornidazole optical antipode by high efficient liquid chromatography Granted publication date: 20070926 License type: Common License Record date: 20131127 |
|
| LICC | Enforcement, change and cancellation of record of contracts on the licence for exploitation of a patent or utility model | ||
| C56 | Change in the name or address of the patentee | ||
| CP03 | Change of name, title or address |
Address after: 210038 No. 9 Zhong Hui Road, Nanjing economic and Technological Development Zone, Nanjing, Jiangsu Patentee after: NANJING SANHOME PHARMACEUTICAL CO., LTD. Address before: 210038, Nanjing economic and Technological Development Zone, Jiangsu Hui Road, No. 9 Patentee before: Nanjing Sanhome Pharmaceutical Co., Ltd. |