CN101271086B - HPLC method for analyzing and separating Trandolapril and impurity - Google Patents
HPLC method for analyzing and separating Trandolapril and impurity Download PDFInfo
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- CN101271086B CN101271086B CN 200710064574 CN200710064574A CN101271086B CN 101271086 B CN101271086 B CN 101271086B CN 200710064574 CN200710064574 CN 200710064574 CN 200710064574 A CN200710064574 A CN 200710064574A CN 101271086 B CN101271086 B CN 101271086B
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Abstract
The invention discloses a high-performance liquid chromatography method for analysis and separation of trandolapril bulk drug and impurities in a preparation thereof, which adopts an alkyl bonding chromatographic column and organic phase-buffer liquid as the mobile phase, thus rapidly analyzing the trandolapril bulk drug, intermediates introduced in the preparation and optical isomer impurities.
Description
Technical field
The invention belongs to the analytical chemistry field, relate to the Analyze & separate method of the impurity in RU-44570 bulk drug and preparation thereof.The intermediate of introducing in high performance liquid chromatography compartment analysis RU-44570 bulk drug and preparation thereof and optical isomer impurity for the present invention, the impurity that can analyze rapidly the RU-44570 bulk drug and contain the RU-44570 preparation by the method.
Background technology
RU-44570 is not containing the angiotensin-converting enzyme inhibitor of sulfydryl, treats essential hypertension and secondary hypertension disease.Its structural formula is:
The structural formula of its optical isomer impurity is:
The structural formula of its intermediate is respectively:
intermediate 1
For the optical isomer impurity of RU-44570 and the intermediate of medicine building-up process, need to carry out quality control.Realizing the compartment analysis of RU-44570 optical isomer impurity and intermediate, is the key that RU-44570 bulk drug and the quality of the pharmaceutical preparations are controlled.
Find through repetition test, use the C18 chromatographic column, the methyl alcohol-damping fluid of certain proportioning of take is mobile phase, optical isomer impurity and the intermediate thereof of RU-44570 effectively can be separated, thereby can accurately control the quality of RU-44570 bulk drug and preparation.Method of the present invention can be simply, compartment analysis RU-44570 optical isomer impurity and its intermediate quickly and accurately.
Summary of the invention
The object of the present invention is to provide the efficient liquid-phase chromatography method of a kind of compartment analysis RU-44570 optical isomer impurity and its intermediate, thereby realize the separation determination of RU-44570 optical isomer impurity and intermediate thereof.
The said method with high performance liquid chromatography compartment analysis RU-44570 optical isomer impurity and intermediate thereof of the present invention, to adopt the chromatographic column that octadecyl silane is filler, methyl alcohol-(phosphate sodium dihydrogen buffer solution, it is mobile phase that phosphoric acid,diluted is adjusted the organic phase-damping fluid of the extremely certain proportioning of pH.
Above-mentioned said chiral chromatographic column is selected from the C18 chromatographic column.
Organic phase of the present invention is selected from following compounds: methyl alcohol, acetonitrile.
Method of the present invention, the volume ratio of organic phase-damping fluid is 80:20 (v/v)～60:40 (v/v).
Above-mentioned said damping fluid is selected from phosphate buffer, and concentration is 0.01mol/L～0.05mol/L.
Method of the present invention, the pH scope of damping fluid is 2.5～4.
Method for separating and analyzing of the present invention, can realize in accordance with the following methods:
(1) get respectively RU-44570, reach each intermediate and optical isomer sample appropriate, be placed in volumetric flask, dissolve with methyl alcohol, be mixed with every 1mL containing RU-44570, the biased sample solution of optical isomer and each intermediate 0.2mg.
(2) flow rate of mobile phase being set is 1.0mL/min, and the detection wavelength is 208nm, and the chromatographic column column oven is room temperature.
(3) get the sample solution 10 μ L injection liquid chromatographies of (1), complete the separation and analysis of RU-44570 and intermediate thereof and optical isomer.
Wherein:
High performance liquid chromatograph: Shimadzu: LC-10ATvp, SPD-M10Avp,
Chromatographic column: C18 (250mm * 4.6mm) chromatographic column
Mobile phase: methyl alcohol-(0.01mol/L sodium dihydrogen phosphate, phosphoric acid,diluted is adjusted pH to 2.5)=72:28 (v/v).
Flow velocity: 1.0mL/min
Column temperature: room temperature
Detect wavelength: 208nm
Sampling volume: 10 μ L
The present invention adopts C18 (250mm * 4.6mm) chromatographic column, effectively compartment analysis RU-44570 intermediate and optical isomer thereof (impurity); Select the methyl alcohol dissolution sample, guaranteed the stability of solution; Select sampling volume 10 μ L, column temperature is room temperature, has improved the symmetry of chromatographic peak.The invention solves containing RU-44570 intermediate and the bulk drug of optical isomer and analysis and the separation problem of preparation, thereby guaranteed the quality controllable of RU-44570 bulk drug and preparation thereof.(the results are shown in accompanying drawing 1)
The accompanying drawing explanation
Fig. 1 is the HPLC figure of condition most preferably
In Fig. 1, No. 1 peak is that 1, No. 2 peaks of intermediate are intermediate 2 and intermediate 4, No. 3 peaks are the RU-44570 main peak, No. 4 peaks are RU-44570 optical isomer (impurity) peak, No. 5 peaks are intermediate 3, can find out at many Pulis of this condition urine main peak and can separate fully with its optical isomer impurity and 4 intermediates, and the RU-44570 main peak is in the 8min left and right.
The HPLC figure that Fig. 2 mobile phase is acetonitrile-damping fluid=70:30
In Fig. 2, No. 1 peak is that 1, No. 2 peaks of intermediate are intermediate 2 and intermediate 4, No. 3 peaks are the RU-44570 main peak, No. 4 peaks are RU-44570 optical isomer (impurity) peak, No. 5 peaks are intermediate 3, can find out at many Pulis of this condition urine main peak and can separate fully with its optical isomer impurity and 4 intermediates, and the RU-44570 main peak is in the 9min left and right.
The HPLC figure that Fig. 3 mobile phase is methyl alcohol-damping fluid=70:30
In Fig. 3, No. 1 peak is that 1, No. 2 peaks of intermediate are intermediate 2 and intermediate 4, No. 3 peaks are the RU-44570 main peak, No. 4 peaks are RU-44570 optical isomer (impurity) peak, No. 5 peaks are intermediate 3, can find out at many Pulis of this condition urine main peak and can separate fully with its optical isomer impurity and 4 intermediates, and the RU-44570 main peak is in the 11min left and right.
The HPLC figure that Fig. 4 damping fluid is pH4
In Fig. 4, No. 1 peak is that 1, No. 2 peaks of intermediate are intermediate 2 and intermediate 4, No. 3 peaks are the RU-44570 main peak, No. 4 peaks are RU-44570 optical isomer (impurity) peak, No. 5 peaks are intermediate 3, can find out at many Pulis of this condition urine main peak and can separate fully with its optical isomer impurity and 4 intermediates, and the RU-44570 main peak is in the 9min left and right.
The HPLC figure that Fig. 5 ion concentration is 0.05mol/L
In Fig. 5, No. 1 peak is that 1, No. 2 peaks of intermediate are intermediate 2 and intermediate 4, No. 3 peaks are the RU-44570 main peak, No. 4 peaks are RU-44570 optical isomer (impurity) peak, No. 5 peaks are intermediate 3, can find out at many Pulis of this condition urine main peak and can separate fully with its optical isomer impurity and 4 intermediates, and the RU-44570 main peak is in the 8min left and right.
Embodiment:
Instrument and condition
High performance liquid chromatograph: Japanese Shimadzu: LC-10Avp, SPD-10Avp;
Chromatographic column: C18 (250mm * 4.6mm);
Mobile phase: acetonitrile-(0.01mol/L sodium dihydrogen phosphate, phosphoric acid,diluted is adjusted pH to 2.5)=60:40
Flow velocity: 1.0mL/min;
Detect wavelength: 208nm;
Column temperature: room temperature;
Sampling volume: 10 μ L.
Experimental procedure
Take respectively each 5mg of each intermediate and RU-44570 and optical isomer thereof, be placed in the 25mL volumetric flask, add mobile phase and dissolve and dilute and put scale, shake up, as biased sample solution.And take respectively single intermediate and RU-44570 and each 5mg of optical isomer thereof, and be placed in respectively 6 25mL volumetric flasks, add mobile phase and dissolve and dilute and put scale, shake up, as qualitative contrast solution.
Get respectively each contrast solution and biased sample solution, by above-mentioned condition, carry out efficient liquid phase chromatographic analysis, record chromatogram.The results are shown in accompanying drawing 2, in figure, No. 1 peak is that 1, No. 2 peaks of intermediate are intermediate 2 and intermediate 4, No. 3 peaks are the RU-44570 main peak, No. 4 peaks are RU-44570 optical isomer (impurity) peak, No. 5 peaks are intermediate 3, can find out at many Pulis of this condition urine main peak and can separate fully with its optical isomer impurity and 4 intermediates, and the RU-44570 main peak is in the 9min left and right.
Instrument and condition
High performance liquid chromatograph: Japanese Shimadzu: LC-10Avp, SPD-10Avp;
Chromatographic column: C18 (250mm * 4.6mm);
Mobile phase: methyl alcohol-(0.01mol/L sodium dihydrogen phosphate, phosphoric acid,diluted is adjusted pH to 2.5)=70:30
Flow velocity: 1.0mL/min;
Detect wavelength: 208nm;
Column temperature: room temperature;
Sampling volume: 10 μ L.
Experimental procedure
Take respectively each 5mg of each intermediate and RU-44570 and optical isomer thereof, be placed in the 25mL volumetric flask, add mobile phase and dissolve and dilute and put scale, shake up, as biased sample solution.And take respectively single intermediate and RU-44570 and each 5mg of optical isomer thereof, and be placed in respectively 6 25mL volumetric flasks, add mobile phase and dissolve and dilute and put scale, shake up, as qualitative contrast solution.
Get respectively each contrast solution and biased sample solution, by above-mentioned condition, carry out efficient liquid phase chromatographic analysis, record chromatogram.The results are shown in accompanying drawing 3, in figure, No. 1 peak is that 1, No. 2 peaks of intermediate are intermediate 2 and intermediate 4, No. 3 peaks are the RU-44570 main peak, No. 4 peaks are RU-44570 optical isomer (impurity) peak, No. 5 peaks are intermediate 3, can find out at many Pulis of this condition urine main peak and can separate fully with its optical isomer impurity and 4 intermediates, and the RU-44570 main peak is in the 11min left and right.
Instrument and condition
High performance liquid chromatograph: Japanese Shimadzu: LC-10Avp, SPD-10Avp;
Chromatographic column: C18 (250mm * 4.6mm);
Mobile phase: methyl alcohol-(0.01mol/L sodium dihydrogen phosphate, phosphoric acid,diluted is adjusted pH to 4)=75:25
Flow velocity: 1.0mL/min;
Detect wavelength: 208nm;
Column temperature: room temperature;
Sampling volume: 10 μ L.
Experimental procedure
Take respectively each 5mg of each intermediate and RU-44570 and optical isomer thereof, be placed in the 25mL volumetric flask, add mobile phase and dissolve and dilute and put scale, shake up, as biased sample solution.And take respectively single intermediate and RU-44570 and each 5mg of optical isomer thereof, and be placed in respectively 6 25mL volumetric flasks, add mobile phase and dissolve and dilute and put scale, shake up, as qualitative contrast solution.
Get respectively each contrast solution and biased sample solution, by above-mentioned condition, carry out efficient liquid phase chromatographic analysis, record chromatogram.The results are shown in accompanying drawing 4, in figure, No. 1 peak is that 1, No. 2 peaks of intermediate are intermediate 2 and intermediate 4, No. 3 peaks are the RU-44570 main peak, No. 4 peaks are RU-44570 optical isomer (impurity) peak, No. 5 peaks are intermediate 3, can find out at many Pulis of this condition urine main peak and can separate fully with its optical isomer impurity and 4 intermediates, and the RU-44570 main peak is in the 9min left and right.
Instrument and condition
High performance liquid chromatograph: Japanese Shimadzu: LC-10Avp, SPD-10Avp;
Chromatographic column: C18 (250mm * 4.6mm);
Mobile phase: methyl alcohol-(0.05mol/L sodium dihydrogen phosphate, phosphoric acid,diluted is adjusted pH to 2.5)=75:25
Flow velocity: 1.0mL/min;
Detect wavelength: 208nm;
Column temperature: room temperature;
Sampling volume: 10 μ L.
Experimental procedure
Take respectively each 5mg of each intermediate and RU-44570 and optical isomer thereof, be placed in the 25mL volumetric flask, add mobile phase and dissolve and dilute and put scale, shake up, as biased sample solution.And take respectively single intermediate and RU-44570 and each 5mg of optical isomer thereof, and be placed in respectively 6 25mL volumetric flasks, add mobile phase and dissolve and dilute and put scale, shake up, as qualitative contrast solution.
Get respectively each contrast solution and biased sample solution, by above-mentioned condition, carry out efficient liquid phase chromatographic analysis, record chromatogram.The results are shown in accompanying drawing 5, in figure, No. 1 peak is that 1, No. 2 peaks of intermediate are intermediate 2 and intermediate 4, No. 3 peaks are the RU-44570 main peak, No. 4 peaks are RU-44570 optical isomer (impurity) peak, No. 5 peaks are intermediate 3, can find out at many Pulis of this condition urine main peak and can separate fully with its optical isomer impurity and 4 intermediates, and the RU-44570 main peak is in the 8min left and right.
Claims (4)
1. the high performance liquid chromatography of a compartment analysis RU-44570, it is characterized in that compartment analysis RU-44570 (I), RU-44570 optical isomer impurity (II), intermediate 1 (III), intermediate 2 (IV), intermediate 3 (V), intermediate 4 (VII): instrument and condition are:
High performance liquid chromatograph: Japanese Shimadzu: LC-10Avp, SPD-10Avp;
Chromatographic column: C18,250mm * 4.6mm;
Mobile phase: acetonitrile-0.01mol/L sodium dihydrogen phosphate=60: 40, described 0.01mol/L sodium dihydrogen phosphate is adjusted pH to 2.5 with phosphoric acid,diluted;
Flow velocity: 1.0mL/min;
Detect wavelength: 208nm;
Column temperature: room temperature;
Sampling volume: 10 μ L;
Take respectively each 5mg of each intermediate and RU-44570 and optical isomer thereof, be placed in the 25mL volumetric flask, add mobile phase and dissolve and be diluted to scale, shake up, as biased sample solution; And take respectively single intermediate and RU-44570 and each 5mg of optical isomer thereof, be placed in respectively 6 25mL volumetric flasks, adding mobile phase dissolves and is diluted to scale, shake up, as qualitative contrast solution, get respectively each contrast solution and biased sample solution, by above-mentioned condition, carry out efficient liquid phase chromatographic analysis, record chromatogram;
2. the high performance liquid chromatography of a compartment analysis RU-44570, it is characterized in that compartment analysis RU-44570 (I), RU-44570 optical isomer impurity (II), intermediate 1 (III), intermediate 2 (IV), intermediate 3 (V), intermediate 4 (VII): instrument and condition are:
High performance liquid chromatograph: Japanese Shimadzu: LC-10Avp, SPD-10Avp;
Chromatographic column: C18,250mm * 4.6mm;
Mobile phase: methyl alcohol-0.01mol/L sodium dihydrogen phosphate=70: 30, described 0.01mol/L sodium dihydrogen phosphate is adjusted pH to 2.5 with phosphoric acid,diluted;
Flow velocity: 1.0mL/min;
Detect wavelength: 208nm;
Column temperature: room temperature;
Sampling volume: 10 μ L;
Take respectively each 5mg of each intermediate and RU-44570 and optical isomer thereof, be placed in the 25mL volumetric flask, add mobile phase and dissolve and be diluted to scale, shake up, as biased sample solution; And take respectively single intermediate and RU-44570 and each 5mg of optical isomer thereof, be placed in respectively 6 25mL volumetric flasks, adding mobile phase dissolves and is diluted to scale, shake up, as qualitative contrast solution, get respectively each contrast solution and biased sample solution, by above-mentioned condition, carry out efficient liquid phase chromatographic analysis, record chromatogram;
3. the high performance liquid chromatography of a compartment analysis RU-44570, it is characterized in that compartment analysis RU-44570 (I), RU-44570 optical isomer impurity (II), intermediate 1 (III), intermediate 2 (IV), intermediate 3 (V), intermediate 4 (VII): instrument and condition are:
High performance liquid chromatograph: Japanese Shimadzu: LC-10Avp, SPD-10Avp;
Chromatographic column: C18,250mm * 4.6mm;
Mobile phase: methyl alcohol-0.01mol/L sodium dihydrogen phosphate=75: 25, described 0.01mol/L sodium dihydrogen phosphate is adjusted pH to 4 with phosphoric acid,diluted;
Flow velocity: 1.0mL/min;
Detect wavelength: 208nm;
Column temperature: room temperature;
Sampling volume: 10 μ L;
Take respectively each 5mg of each intermediate and RU-44570 and optical isomer thereof, be placed in the 25mL volumetric flask, add mobile phase and dissolve and be diluted to scale, shake up, as biased sample solution; And take respectively single intermediate and RU-44570 and each 5mg of optical isomer thereof, be placed in respectively 6 25mL volumetric flasks, adding mobile phase dissolves and is diluted to scale, shake up, as qualitative contrast solution, get respectively each contrast solution and biased sample solution, by above-mentioned condition, carry out efficient liquid phase chromatographic analysis, record chromatogram:
4. the high performance liquid chromatography of a compartment analysis RU-44570, it is characterized in that compartment analysis RU-44570 (I), RU-44570 optical isomer impurity (II), intermediate 1 (III), intermediate 2 (IV), intermediate 3 (V), intermediate 4 (VII): instrument and condition are:
High performance liquid chromatograph: Japanese Shimadzu: LC-10Avp, SPD-10Avp;
Chromatographic column: C18,250mm * 4.6mm;
Mobile phase: methyl alcohol-0.05mol/L sodium dihydrogen phosphate=75: 25, described 0.01mol/L sodium dihydrogen phosphate is adjusted pH to 2.5 with phosphoric acid,diluted;
Flow velocity: 1.0mL/min;
Detect wavelength: 208nm;
Column temperature: room temperature;
Sampling volume: 10 μ L;
Take respectively each 5mg of each intermediate and RU-44570 and optical isomer thereof, be placed in the 25mL volumetric flask, add mobile phase and dissolve and be diluted to scale, shake up, as biased sample solution; And take respectively single intermediate and RU-44570 and each 5mg of optical isomer thereof, be placed in respectively 6 25mL volumetric flasks, adding mobile phase dissolves and is diluted to scale, shake up, as qualitative contrast solution, get respectively each contrast solution and biased sample solution, by above-mentioned condition, carry out efficient liquid phase chromatographic analysis, record chromatogram;
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Non-Patent Citations (1)
| Title |
|---|
| Cendrowska I,et al.a study on the stereochemical purity of trandolapril and octahydro-1h-indole-2-carboxylic acid by HPLC method.《Acta Pol Pharm》.2003,第60卷(第2期),第141－144页. * |
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