CN106680413B - A kind of RT-HPLC detection method of the sodium azulenesulfonate in relation to substance - Google Patents
A kind of RT-HPLC detection method of the sodium azulenesulfonate in relation to substance Download PDFInfo
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Abstract
The present invention relates to Pharmaceutical Analysis technical fields, disclose a kind of RT-HPLC detection method of the sodium azulenesulfonate in relation to substance, include the following steps：Allocation Analysis solution；Chromatographic condition；Upper machine measures.At present, the complete patent of correlation temporarily not about sodium azulenesulfonate in relation to substance detecting method and document report.The present invention, which can effectively measure various related impurities in sodium azulenesulfonate, to be existed, especially not only realize sodium azulenesulfonate characteristic peak and its isomers characteristic peak in spectrogram, and realize the separation of sodium azulenesulfonate characteristic peak and more degradation impurity characteristic peak in spectrogram, so that it is guaranteed that product is quality controllable.
Description
Technical field
The present invention relates to Pharmaceutical Analysis technical field, more particularly to reversed efficient liquid phase of a kind of sodium azulenesulfonate in relation to substance
Chromatographic detection method.
Background technology
So-called in Pharmaceutical Analysis " related substance (related substances) " refers in production of raw medicine process
In the substances such as starting material, reagent, intermediate, by-product and the isomers brought into, it is also possible to preparation is in production, storage and fortune
The special impurities such as catabolite, polymer or the crystal transfer generated during defeated.The synthesis of type and drug in relation to substance
Route is closely related with preparation process, and drug may all lead to it in the change of any one of synthesis and production process factor
Type in relation to substance is different, thus related substance to detect and control process relative complex.Detection in relation to substance is control
The important indicator of drug quality.
Sodium azulenesulfonate (Sodium Azulene Sulfonate) also known as Sodium Gualenate, are to spend middle extraction from feverfew
A kind of chemical substance, research in recent years finds it with following effects：Inhibit inflammation caused by a variety of inflammation-causing substances, and act on compared with
It is lasting；Inflammatory cell is inhibited to discharge histamine by part directly effect；Increase the synthesis of prostaglandin E2 in mucous membrane, promotes meat
Bud is formed and epithelial cell is newborn；Reduce the activity of pepsin.
Sodium azulenesulfonate, the entitled Isosorbide-5-Nitrae-dimethyl -7- isopropyl Azulene -3- sodium sulfonates of chemistry, structural formula are as follows：
The related substance of sodium azulenesulfonate is as follows：Kessazulen, impurity A, impurity B, impurity C, wherein Kessazulen close for sodium azulenesulfonate
At the starting material of technique；Impurity A is sodium azulenesulfonate isomer；Impurity B, impurity C are oxidative degradation impurity, above-mentioned impurity
Structure is shown in Table 1.
Each impurity title of 1 sodium azulenesulfonate of table and structure
Only the total content in relation to substance is defined in the domestic and international published drug standards about sodium azulenesulfonate,
And the content of any single contaminant is not limited.The outer pharmaceuticals ingredient specification (1989) of Pharmacopeia of Japan records bulk pharmaceutical chemicals,
To the related substance Kessazulen in sample using adding n-hexane to filter, filtrate is measured with the method that photometry measures transmitance, spirit
Sensitivity is low.When sodium azulenesulfonate is applied to different preparations as bulk pharmaceutical chemicals, the content for detecting its related impurities is needed, judges sodium sulfonate
Whether bulk pharmaceutical chemicals are qualified, if need that correlation means is taken to be controlled.The method of existing literature report can not detach above-mentioned miscellaneous
Matter, it is even more impossible to determine its concrete content.
Invention content
To solve the above-mentioned problems, the present invention provides a kind of RT-HPLC detection method of the sodium azulenesulfonate in relation to substance, passes through
With phenyl silane reverse-phase chromatographic column, gradient appropriate is adjusted, sodium azulenesulfonate characteristic peak is solved and its isomers, oxidation is miscellaneous
The problem of matter characteristic peak detaches, realizes the control to sodium azulenesulfonate bulk pharmaceutical chemicals quality, and the method high sensitivity, specificity
By force, easy to operate.
Detection method of the sodium azulenesulfonate in relation to substance RT-HPLC of the present invention, includes the following steps：
A) Allocation Analysis solution
B) chromatographic condition
Chromatographic column is reverse-phase chromatographic column, described using acid or phosphate aqueous phase solution and the mixed liquor of organic phase as mobile phase
Aqueous phase solution is faintly acid, and the organic phase is selected from methanol；Using gradient elution method, the gradient elution method mobile phase
Middle water phase volume ratio by 0,8~12,39~44,48~53,55~58min time points, water phase volume ratio is 95-98%, 85-
90%, 85-90%, 30-40%, 25-30% carry out gradient elution；
C) machine measures on
It takes analytical solution 5-30 μ l made of step a) to inject high performance liquid chromatograph, carries out chromatography, and record color
Spectrogram.
Preferred embodiment, step a) the sample analysis solution preparation follow claimed below：It is molten with methanol-phosphate aqueous solution
Sample is solved, analytical solution is made, organic phase percent by volume is more than 50% in the methanol-phosphate aqueous solution.The step
In rapid b) chromatographic condition, efficient liquid phase flow velocity is set as 0.8-1.2ml/min；Column temperature be 25-50 DEG C, use Detection wavelength for
220-300nm UV detector；
In some embodiments, the filler of the reverse-phase chromatographic column is phenyl silane bonded silica gel chromatographic column or octadecane
Base silane bonded silica gel chromatographic column or eight alkyl silane bonded silica gel chromatographic columns, preferably phenyl silane bonded silica gel chromatographic column.
In some embodiments, the specification of the reverse-phase chromatographic column is：Column length is between 100mm to 300mm, chromatography column internal diameter
Between 1mm to 10mm, grain size is between 1 μm to 10 μm, and preferably specification is 4.6mm × 250mm, 5 μm of phenyl silane bonded silica
Glue chromatographic column.
In some embodiments, a concentration of 0.001-0.05mol/L, pH 2.0-4.0 of the phosphate solution, preferably
A concentration of 0.02mol/L, pH 2.7-3.5 of phosphate solution.
In some embodiments, the phosphate is sodium phosphate, sodium dihydrogen phosphate, disodium hydrogen phosphate, potassium phosphate, di(2-ethylhexyl)phosphate
One of hydrogen potassium, dipotassium hydrogen phosphate, preferably potassium dihydrogen phosphate.
In some embodiments, the A phases are phosphate solution-methanol, and the volume ratio of the phosphate solution-methanol is
10:90-80:20, preferred volume ratio 80:20.
Preferred embodiment is：Step a) methanol-phosphate aqueous solution sample dissolutions, are made analytical solution, the methanol-
Organic phase percent by volume is more than 50% in phosphate aqueous solution；Step b) is that the condition of gradient elution is that reverse-phase chromatographic column is
The phenyl silane bonded silica gel chromatographic column of column length 250mm, diameter 4.6mm, 5 μm of packing material size, mobile phase be with 0.02mol/L,
3.0 potassium dihydrogen phosphates of pH-methanol is A phases, in mobile phase A phases-methanol ratio by 0,10,40,50,58min time points, A
Phase volume ratio is 97%, 88%, 85%, 35%, 30% progress gradient elution, flow velocity 1.0ml/min；30 DEG C of column temperature detects wave
Long 245nm；Step c) takes analytical solution made of step a) to inject high performance liquid chromatograph, carries out chromatography, and record color
Spectrum.
In some embodiments, the sample is sodium azulenesulfonate or its related preparations.The sodium azulenesulfonate related preparations are
Tablet, granule.
Above method analysis can be used for detaching impurity A, impurity B, impurity C, Kessazulen, sodium azulenesulfonate in sample.
The present invention can effectively measure the presence of various related impurities in sodium azulenesulfonate solution, especially realize in spectrogram
Sodium azulenesulfonate characteristic peak and sodium azulenesulfonate isomer characteristic peak and its point of related starting material, oxidation impurities characteristic peak
From.The separating degree of each impurity is all higher than 1.5, and wherein sodium azulenesulfonate reaches 3.5 with its isomer separating degree, tailing factor
2.5 hereinafter, theoretical cam curve 8000 or more.A kind of related substance method of detection sodium azulenesulfonate of this technology invention, the detection
Method is simple, quick, high sensitivity, accuracy are high.
The detection of the above method may insure the quality controllable of product.
Description of the drawings
The chromatogram of Fig. 1,1 mobile phase condition of embodiment；
The chromatogram of Fig. 2,2 mobile phase condition of embodiment；
The chromatogram of Fig. 3,3 gradient wash of embodiment.
The chromatogram of Fig. 4,4 gradient wash of embodiment.
The chromatogram of Fig. 5,5 gradient wash of embodiment.
Specific implementation mode
With reference to the accompanying drawings of the specification and specific embodiment, the present invention is described in detail.These embodiments are only used for
Illustrate the present invention rather than limits the scope of the invention.The test method of actual conditions is not specified in the following example, usually
According to normal condition or according to the normal condition proposed by manufacturer.In addition, any method similar or impartial to described content
And material all can be used in the method for the present invention.The preferred methods and materials described herein are for illustrative purposes only.
Embodiment one
(1) instrument and chromatographic condition
High performance liquid chromatograph：U3000 highly effective liquid phase chromatographic systems and work station；
Chromatographic column：The phenyl silane bonded silica gel chromatographic column of SUPELCOSILLC-DP (4.6mm × 250mm, 5 μm)
It is A phases (with phosphorus acid for adjusting pH to 3.0) to configure 0.02mol/L potassium dihydrogen phosphates, A phases-methanol in mobile phase
Ratio by 0,5,15,40,45,46,52min time points, A phase volume ratios are 88%, 88%, 60%, 25%, 25%, 88%,
88% carries out gradient elution, flow velocity 1.0ml/min；30 DEG C of column temperature, Detection wavelength 245nm；
(2) experimental procedure
It takes sodium azulenesulfonate reference substance, impurity A, impurity B, impurity C and Kessazulen reference substance each appropriate respectively, uses solvent
[0.02mol/L potassium dihydrogen phosphates (with phosphorus acid for adjusting pH to 3.0)-methanol (30:70)]Every ml is made and contains sodium azulenesulfonate
0.5mg, other each impurity respectively contain the system suitability solution of 5 μ g, as analytical solution；
10 μ l of above-mentioned analytical solution are taken, liquid chromatograph is injected, record chromatogram.As a result see attached drawing 1, it can be seen that this
Sodium azulenesulfonate main peak and its isomer impurity A peak fail complete baseline separation under part.
Embodiment two
(1) instrument and chromatographic condition
High performance liquid chromatograph：U3000 highly effective liquid phase chromatographic systems and work station；
Chromatographic column：The phenyl silane bonded silica gel chromatographic column of SUPELCOSILLC-DP (4.6mm × 250mm, 5 μm)
It is A phases (with phosphorus acid for adjusting pH to 3.0) to configure 0.02mol/L potassium dihydrogen phosphates, A phases-methanol in mobile phase
Ratio by 0,5,15,45,50,51,55min time points, A phase volume ratios are 88%, 88%, 70%, 40%, 25%, 88%,
88% carries out gradient elution, flow velocity 1.0ml/min；30 DEG C of column temperature, Detection wavelength 245nm；
(2) experimental procedure
It takes sodium azulenesulfonate reference substance, impurity A, impurity B, impurity C and Kessazulen reference substance each appropriate respectively, uses solvent
[0.02mol/L potassium dihydrogen phosphates (with phosphorus acid for adjusting pH to 3.0)-methanol (30:70)]Every ml is made and contains sodium azulenesulfonate
0.5mg, other each impurity respectively contain the system suitability solution of 5 μ g, as analytical solution；
10 μ l of above-mentioned analytical solution are taken, liquid chromatograph is injected, record chromatogram.As a result see attached drawing 2, it can be seen that this
Sodium azulenesulfonate main peak and its isomer impurity A peak still fail complete baseline separation under part.
Embodiment three
(1) instrument and chromatographic condition
High performance liquid chromatograph：U3000 highly effective liquid phase chromatographic systems and work station；
Chromatographic column：The phenyl silane bonded silica gel chromatographic column of SUPELCOSILLC-DP (4.6mm × 250mm, 5 μm)
It is A phases, wherein water phase and first to configure 0.02mol/L potassium dihydrogen phosphates (with phosphorus acid for adjusting pH to 3.0)-methanol
Alcohol phase volume ratio is 80:20, in mobile phase the ratio of A phases-methanol by 0,10,40,50,58,58.1,63min time points, A phases
Volume ratio is 97%, 88%, 85%, 35%, 30%, 97%, 97% progress gradient elution, flow velocity 1.0ml/min；Column temperature 30
DEG C, Detection wavelength 245nm；
(2) experimental procedure
It takes sodium azulenesulfonate reference substance, impurity A, impurity B, impurity C and Kessazulen reference substance each appropriate respectively, uses solvent
[0.02mol/L potassium dihydrogen phosphates (with phosphorus acid for adjusting pH to 3.0)-methanol (30:70)]Every ml is made and contains sodium azulenesulfonate
0.5mg, other each impurity respectively contain the system suitability solution of 5 μ g, as analytical solution；
10 μ l of above-mentioned analytical solution are taken, liquid chromatograph is injected, record chromatogram.As a result see shown in attached drawing 3 and table 1, it can
It is efficiently separated with finding out that each peak separating degree can reach under this condition, wherein sodium azulenesulfonate main peak and its isomer impurity A
Peak is kept completely separate, separating degree 3.05, and each peak theoretical cam curve is all higher than 8000.
1 embodiment of table, 3 chromatographic results table
Example IV
(1) instrument and chromatographic condition
High performance liquid chromatograph：U3000 highly effective liquid phase chromatographic systems and work station；
Chromatographic column：The phenyl silane bonded silica gel chromatographic column of SUPELCOSILLC-DP (4.6mm × 250mm, 5 μm)
It is A phases, wherein water phase and first to configure 0.02mol/L potassium dihydrogen phosphates (with phosphorus acid for adjusting pH to 2.8)-methanol
Alcohol phase volume ratio is 80:20, in mobile phase the ratio of A phases-methanol by 0,10,40,50,58,58.1,63min time points, A phases
Volume ratio is 97%, 88%, 85%, 35%, 30%, 97%, 97% progress gradient elution, flow velocity 0.8ml/min；Column temperature 30
DEG C, Detection wavelength 245nm；
(2) experimental procedure
It takes sodium azulenesulfonate reference substance, impurity A, impurity B, impurity C and Kessazulen reference substance each appropriate respectively, uses solvent
[0.02mol/L potassium dihydrogen phosphates (with phosphorus acid for adjusting pH to 3.0)-methanol (30:70)]Every ml is made and contains sodium azulenesulfonate
0.5mg, other each impurity respectively contain the system suitability solution of 5 μ g, as analytical solution；
10 μ l of above-mentioned analytical solution are taken, liquid chromatograph is injected, record chromatogram.As a result see attached drawing 4.
Embodiment five
(1) instrument and chromatographic condition
High performance liquid chromatograph：U3000 highly effective liquid phase chromatographic systems and work station；
Chromatographic column：The phenyl silane bonded silica gel chromatographic column of SUPELCOSILLC-DP (4.6mm × 250mm, 5 μm)
It is A phases, wherein water phase and first to configure 0.02mol/L potassium dihydrogen phosphates (with phosphorus acid for adjusting pH to 3.2)-methanol
Alcohol phase volume ratio is 80:20, in mobile phase the ratio of A phases-methanol by 0,10,40,50,58,58.1,63min time points, A phases
Volume ratio is 97%, 88%, 85%, 35%, 30%, 97%, 97% progress gradient elution, flow velocity 1.2ml/min；Column temperature 30
DEG C, Detection wavelength 245nm；
(2) experimental procedure
It takes sodium azulenesulfonate reference substance, impurity A, impurity B, impurity C and Kessazulen reference substance each appropriate respectively, uses solvent
[0.02mol/L potassium dihydrogen phosphates (with phosphorus acid for adjusting pH to 3.0)-methanol (30:70)]Every ml is made and contains sodium azulenesulfonate
0.5mg, other each impurity respectively contain the system suitability solution of 5 μ g, as analytical solution；
10 μ l of above-mentioned analytical solution are taken, liquid chromatograph is injected, record chromatogram.As a result see attached drawing 5.
Claims (4)
1. a kind of RT-HPLC detection method of sodium azulenesulfonate in relation to substance, which is characterized in that include the following steps：
A) sample to be tested analytical solution is configured
B) chromatographic condition
Reverse-phase chromatographic column is phenyl silane bonded silica gel chromatographic column, and mobile phase is molten with 3.0 potassium dihydrogen phosphate of 0.02mol/L, pH
Liquid/phosphoric acid solution-methanol is A phases, and B phases are methanol, and A, B mix into mobile phase, the volume ratio of the phosphate solution-methanol
It is 80:20；Using gradient elution method, in the gradient elution method mobile phase water phase volume ratio by 0,10,40,50,58,
58.1,63min time points, the volume ratio that A phases account for mobile phase are 97%, 88%, 85%, 35%, 30%, 97%, 97% progress
Gradient elution；
C) machine measures on
It takes analytical solution made of step a) to inject high performance liquid chromatograph, carries out chromatography, and record chromatography
The method is for detaching impurity A in sampleImpurity B
Impurity CKessazulen, sodium azulenesulfonate.
2. RT-HPLC detection methods as described in claim 1, which is characterized in that
Step a) configures sample to be tested analytical solution specific method：With methanol-phosphate aqueous solution sample dissolution, it is molten that analysis is made
Liquid, organic phase percent by volume is more than 50% in the methanol-phosphate aqueous solution；
In step b) chromatographic conditions, efficient liquid phase flow velocity is set as 0.8-1.2ml/min；Column temperature is 25-50 DEG C, using detection wave
A length of 220-300nm UV detector.
3. RT-HPLC detection methods as described in claim 1, which is characterized in that the specification of the reverse-phase chromatographic column is：Column length
Between 100mm to 300mm, chromatography column internal diameter is between 1mm to 10mm, and grain size is between 1 μm to 10 μm.
4. RT-HPLC detection methods as described in claim 1, which is characterized in that the step b) is the gradient elution item
Part be reverse-phase chromatographic column be column length 250mm, the phenyl silane bonded silica gel chromatographic column of diameter 4.6mm, 5 μm of packing material size, flowing
Mutually to be A phases with 3.0 potassium dihydrogen phosphates of 0.02mol/L, pH-methanol, the volume ratio of the phosphate solution-methanol is
80:20, in mobile phase A phase-B Phase Proportions by 0,10,40,50,58,58.1,63min time points, A phase volume ratios are 97%,
88%, 85%, 35%, 30%, 97%, 97% gradient elution, flow velocity 1.0ml/min are carried out；30 DEG C of column temperature, Detection wavelength
245nm。
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| CN103385863B (en) * | 2013-08-05 | 2015-07-15 | 四川国康药业有限公司 | Sodium azulene sulfonate sustained-release preparation |
| CN103512976B (en) * | 2013-09-18 | 2017-08-25 | 河北凯盛医药科技有限公司 | A kind of analyzing detecting method of Azulene sulfonic acid isomers and its salt |
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