CN113030282A - Method for analyzing and detecting substances related to phthalimide potassium salt - Google Patents
Method for analyzing and detecting substances related to phthalimide potassium salt Download PDFInfo
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Abstract
The invention provides a method for detecting related substances in phthalimide potassium salt, which adopts high performance liquid chromatography, takes any one of octadecylsilane chemically bonded silica, octylsilane chemically bonded silica or phenyl chemically bonded silica as a stationary phase, and takes any one or a combination of a buffer salt solution and an organic solvent as a mobile phase for elution. The method can simultaneously separate and quantitatively detect impurities possibly existing in the phthalimide potassium salt, thereby effectively controlling the quality of the phthalimide potassium. The method is simple and convenient, good in repeatability and strong in specificity.
Description
Technical Field
The invention relates to the technical field of drug analysis methods, in particular to a method for analyzing and detecting related substances in phthalimide potassium salt.
Background
The potassium phthalimide salt is widely used for producing medicines, pesticides, dyes, synthetic primary amine compounds and the like, and the content of the potassium phthalimide salt is usually determined by non-aqueous titration. The structure of the phthalimide potassium salt is as follows:
the above impurities are all referred to as phthalimide potassium salts, and strict quality control is required.
The existing reported methods for analyzing and detecting the potassium phthalimide salt mainly aim at quantitative or qualitative analysis of the potassium phthalimide salt, but no report is found on the analysis and research of substances related to the potassium phthalimide salt. Therefore, there is a need to establish a stable and effective analytical detection method for quality control of phthalimide potassium salt.
Disclosure of Invention
In view of this, the technical problem to be solved by the present invention is to provide a method for separating and detecting related substances in phthalimide potassium salt by high performance liquid chromatography, which can effectively separate and quantitatively determine potential impurities in phthalimide potassium salt, and has the advantages of strong specificity, high sensitivity, good repeatability and good accuracy. The invention provides an analysis and detection method of phthalimide potassium salt related substances, which comprises the following steps:
dissolving phthalimide potassium salt in a diluent by adopting a high performance liquid chromatography to prepare a phthalimide potassium solution, eluting by using an ultraviolet detector and any one of octadecylsilane chemically bonded silica, octylsilane chemically bonded silica or phenyl chemically bonded silica as a stationary phase and any one or a combination of a buffer salt solution and an organic solvent as a mobile phase, and recording a chromatogram;
optionally, the mobile phase is a mixed solution of a buffered salt solution and an organic solvent.
Optionally, the pH of the buffered salt solution is 0.5-5.0; preferably, the pH is 1.0-3.0;
optionally, the pH of the buffered salt solution is adjusted with at least one selected from the group consisting of phosphoric acid, formic acid, acetic acid, perchloric acid.
Optionally, the diluent is selected from at least one of acetonitrile, tetrahydrofuran, 1, 4-dioxane, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, dimethyl sulfoxide, N-dimethylformamide and N, N-dimethylacetamide; dimethyl sulfoxide is preferred.
Optionally, the stationary phase is any one of octadecylsilane chemically bonded silica, octylsilane chemically bonded silica or phenyl chemically bonded silica modified by a special side chain group, and the particle size of the filler is 1.7-5 μm;
alternatively, the stationary phase is Agilent Infinity Lab Poroshell 120SB-AQ with a specification of 4.6mmx150mm and a filler particle size of 2.7 μm.
Optionally, a tail scavenging agent can be further added into the buffered salt solution, and the tail scavenging agent is selected from any one or combination of diethylamine and triethylamine;
optionally, the volume concentration of the tail-sweeping agent in the mobile phase is 0.01-0.5%.
Optionally, the buffered salt solution in the mobile phase is selected from at least one of potassium dihydrogen phosphate, sodium dihydrogen phosphate, ammonium dihydrogen phosphate, dipotassium hydrogen phosphate, disodium hydrogen phosphate, diammonium hydrogen phosphate, ammonium acetate buffer.
Optionally, the organic solvent in the mobile phase is selected from at least one of alcohols, acetonitrile, amides and ketones;
optionally, the organic solvent in the mobile phase is selected from at least one of methanol, ethanol, isopropanol, acetonitrile, formamide, and acetone;
optionally, the organic solvent in the mobile phase is selected from at least one of methanol and acetonitrile.
Optionally, the concentration of the buffered salt solution is 0.001mol/L to 1.0mol/L, preferably 0.005mol/L to 0.05 mol/L.
Optionally, the volume ratio of the buffered salt solution to the organic solvent in the mobile phase is 75-85: 15-25;
optionally, the volume ratio of the buffered salt solution to the organic solvent in the mobile phase is 80: 20.
optionally, the sample amount of the analysis detection method is 5-20 μ l; the flow rate of the mobile phase is 0.5-1.5 ml/min; the column temperature of the stationary phase is 20-40 ℃, and preferably 20-30 ℃; the chromatogram is a chromatogram recorded at a detection wavelength of 200-230 nm; the concentration of the phthalimide potassium solution is 0.5mg/ml to 1.5 mg/ml;
optionally, the sample size of the analytical detection method is 10 μ l; the flow rate of the mobile phase is 1.0 ml/min; the column temperature of the stationary phase is 25 ℃; the chromatogram is a chromatogram recorded at a detection wavelength of 233 nm; the concentration of the phthalimide potassium solution is 0.8mg/ml to 1.5 mg/ml.
Optionally, the relevant substances are:
due to the particularity of the chemical structure of the phthalimide potassium salt, the phthalimide potassium salt is very easy to hydrolyze in the presence of water, and the method creatively solves the problems of hydrolysis of the phthalimide potassium salt, retention of impurities under a liquid phase condition and asymmetric impurity peak shape. The method can effectively separate and quantitatively determine impurities possibly existing in the phthalimide potassium salt, thereby effectively controlling the quality of the phthalimide potassium salt. The method has the advantages of strong specificity, high sensitivity, good repeatability and good accuracy. The method fills the technical blank of the quality control of the phthalimide potassium salt in the prior art, has mild detection conditions, has no harsh requirements on a high performance liquid chromatography instrument, an analytical reagent and a chromatographic column, and can be suitable for common chromatographic columns and high performance liquid chromatography instruments.
Obviously, many modifications, substitutions, and variations are possible in light of the above teachings of the invention, without departing from the basic technical spirit of the invention, as defined by the following claims.
The present invention will be described in further detail with reference to the following examples. This should not be understood as limiting the scope of the above-described subject matter of the present invention to the following examples. All the technologies realized based on the above contents of the present invention belong to the scope of the present invention.
Drawings
FIG. 1 is a high performance liquid chromatogram of an air-white solvent of example 1;
FIG. 2 is a high performance liquid chromatogram of a control solution of anthranilic acid of example 1;
FIG. 3 is a high performance liquid chromatogram of a control solution of phthalic acid in example 1;
FIG. 4 is a high performance liquid chromatogram of potassium phthalimide of example 1;
FIG. 5 is a high performance liquid chromatogram of potassium phthalimide of example 3, wherein the diluent used is dimethyl sulfoxide;
FIG. 6 is a high performance liquid chromatogram of potassium phthalimide of example 3, wherein the diluent used is 50% (v/v) aqueous dimethyl sulfoxide;
FIG. 7 is a high performance liquid chromatogram of potassium phthalimide in comparative example 1.
Detailed Description
The present invention is described in further detail below with reference to examples, but it should not be construed that the scope of the above subject matter is limited to the examples. All the technologies realized based on the above contents of the present invention belong to the scope of the present invention.
The o-carbamyl benzoic acid impurity used in the invention is self-made; the rest products are purchased and obtained on the market.
Example 1 degree of separation test
(1) Chromatographic conditions
The instrument comprises the following steps: a high-efficiency liquidus chromatograph Agilent 1260;
a chromatographic column: agilent Infinity Lab Poroshell 120SB-AQ (4.6 mm. times.150 mm, 2.7 μm);
mobile phase: 0.01mol/L sodium dihydrogen phosphate (containing 0.1% triethylamine, pH adjusted by phosphoric acid 2.0) methanol 80:20 (v/v);
detection wavelength: 233 nm;
flow rate: 1.0 ml/min;
sample introduction amount: 10 mu l of the mixture;
column temperature: 25 ℃;
collecting time: and (3) 30 min.
(2) Solution preparation
Diluent agent: dimethyl sulfoxide;
blank solution: a diluent;
test solution: taking 20mg of phthalimide potassium, precisely weighing, placing in a 25ml volumetric flask, dissolving and diluting to a scale with a diluent, and shaking up to obtain the phthalimide potassium.
Control solution: taking a proper amount of potassium hydrogen phthalate (about 20mg equivalent to phthalic acid), precisely weighing, placing in a 100ml volumetric flask, adding a diluent to dissolve and dilute to a scale, and shaking up. Precisely measuring 1.0ml, placing into a 50ml volumetric flask, adding a diluent to dilute to a scale, and shaking up to obtain the product.
O-carbamoylbenzoic acid control solution: taking a proper amount of the impurity o-carbamoylbenzoic acid, and adding the diluent to prepare a solution containing o-carbamoylbenzoic acid about 4 mu g/mL.
Phthalic acid control solution: taking a proper amount of impurity phthalic acid, and adding the diluent to prepare a solution containing the o-carbamoylbenzoic acid of about 4 mu g/mL.
(3) Assay method
Testing according to the above chromatographic conditions, sampling blank solution, sample solution, reference solution, and impurity reference solution respectively, and recording chromatogram.
(4) Measurement results
Typical chromatograms are shown in FIGS. 1-4. FIG. 1 is a blank solvent chromatogram. FIG. 2 is a chromatogram of a control solution containing impurity o-carbamoylbenzoic acid, wherein the retention time of a chromatographic peak is 3.085 min. FIG. 3 is a chromatogram of a control solution of impurity phthalic acid, wherein the retention time of a chromatographic peak is 6.189 min. FIG. 4 is a chromatogram of a sample solution, in which a peak at a retention time of 11.305min is a phthalimide potassium peak, a peak at 3.081min is an impurity carbamoylbenzoic acid peak, a peak at 5.973min is an impurity phthalic acid peak, and peaks at 9.527min and 13.772min are unknown impurity peaks. As can be seen from the figures 1 to 4, the blank solvent does not interfere with the measurement, the potassium phthalimide and each impurity thereof can achieve good separation, the separation degrees between impurity peaks and between a main peak and an adjacent impurity peak are both greater than 1.5, and the requirements of Chinese pharmacopoeia are met.
Example 2 phthalic anhydride accuracy determination
(1) Chromatographic conditions
The instrument comprises the following steps: a high-efficiency liquidus chromatograph Agilent 1260;
a chromatographic column: agilent Infinity Lab Poroshell 120SB-AQ (4.6 mm. times.150 mm, 2.7 μm);
mobile phase: 0.01mol/L sodium dihydrogen phosphate (containing 0.1% triethylamine, pH adjusted by phosphoric acid 2.0) methanol 80:20 (v/v);
detection wavelength: 233 nm;
flow rate: 1.0 ml/min;
sample introduction amount: 10 mu l of the mixture;
column temperature: 25 ℃;
collecting time: 30 min;
(2) solution preparation
Diluent agent: 50% (v/v) aqueous dimethyl sulfoxide;
blank solution: a diluent;
phthalic acid control stock solution: taking 27.57mg of potassium hydrogen phthalate (equivalent to 20mg of phthalic anhydride), precisely weighing, placing in a 100ml volumetric flask, diluting with a diluent to a scale to obtain the product (equivalent to 200 mu g/ml of phthalic anhydride), and preparing two parts in parallel.
Phthalic acid control solution: 1.0ml of phthalic acid control stock solution was precisely measured into a 50ml volumetric flask, and diluted to the scale with a diluent (equivalent to phthalic anhydride concentration: 4. mu.g/ml).
Phthalic anhydride control stock: precisely weighing about 20mg of phthalic anhydride, placing in a 100ml volumetric flask, and diluting the diluent to scale (phthalic anhydride concentration: 4 mug/ml)
Test solution: 20mg of potassium phthalimide is precisely weighed, placed in a 25-volume flask, dissolved and diluted to the scale by a diluent, and shaken up. (2 parts)
Adding a standard solution into a test sample: 20mg of potassium phthalimide is precisely weighed and placed in a 25ml volumetric flask, a small amount of diluent is firstly added for dissolution, 0.5ml of phthalic anhydride contrast stock solution is then added, the diluent is added for dilution to the scale, shaking up is carried out (the phthalic anhydride is added to the limit concentration of 4 mug/ml), and 6 parts are prepared by the same method.
(3) Assay method
Measuring the phthalic acid control solution, the test sample solution and the test sample and standard solution according to the chromatographic conditions, and calculating the sample recovery rate according to the following formula:
percent recovery is (c-a)/b × 100%;
wherein a is the measured component content of the test sample; b is the amount of the added reference substance; c is an actual measurement value.
(4) Measurement results
The results are shown in Table 1, and the average recovery of phthalic anhydride was 109.6%. The method for detecting phthalic anhydride has high accuracy.
TABLE 1 phthalic anhydride accuracy measurement results
EXAMPLE 3 measurement of content of substance of interest in Potassium phthalimide salt
A. Content determination of o-carbamoylbenzoic acid, phthalic acid and unknown impurities in phthalimide potassium salt
(1) Chromatographic conditions
The instrument comprises the following steps: a high-efficiency liquidus chromatograph Agilent 1260;
a chromatographic column: agilent Infinity Lab Poroshell 120SB-AQ (4.6 mm. times.150 mm,
2.7μm)；
mobile phase: 0.01mol/L sodium dihydrogen phosphate (containing 0.1% triethylamine, pH adjusted by phosphoric acid 2.0) methanol 80:20 (v/v);
detection wavelength: 233 nm;
flow rate: 1.0 ml/min;
sample introduction amount: 10 mu l of the mixture;
column temperature: 25 ℃;
collecting time: and (3) 30 min.
(2) Solution preparation
Diluent agent: dimethyl sulfoxide;
blank solution: a diluent;
test solution: taking 20mg of phthalimide potassium, precisely weighing, placing in a 25ml volumetric flask, dissolving and diluting to a scale with a diluent, and shaking up to obtain the phthalimide potassium.
Control solution: taking a proper amount of potassium hydrogen phthalate (about 20mg equivalent to phthalic acid), precisely weighing, placing in a 100ml volumetric flask, adding a diluent to dissolve and dilute to a scale, and shaking up. Precisely measuring 1.0ml, placing into a 50ml volumetric flask, adding a diluent to dilute to a scale, and shaking up to obtain the product.
(3) Assay method
Testing according to the above chromatographic conditions, sampling blank solution, control solution and sample solution respectively, and recording chromatogram.
(4) Measurement results
A typical chromatogram is shown in FIG. 5. The test results of the test solutions are shown in Table 2. And calculating the content of the impurities by an area normalization method.
TABLE 2 test results of the test solutions
B. Content determination of phthalic anhydride in phthalimide potassium salt
(1) Chromatographic conditions
The instrument comprises the following steps: a high-efficiency liquidus chromatograph Agilent 1260;
a chromatographic column: agilent Infinity Lab Poroshell 120SB-AQ (4.6 mm. times.150 mm, 2.7 μm);
mobile phase: 0.01mol/L sodium dihydrogen phosphate (containing 0.1% triethylamine, pH adjusted by phosphoric acid 2.0) methanol 80:20 (v/v);
detection wavelength: 233 nm;
flow rate: 1.0 ml/min;
sample introduction amount: 10 mu l of the mixture;
column temperature: 25 deg.C
Collecting time: and (3) 30 min.
(2) Solution preparation
Diluent agent: 50% (v/v) aqueous dimethyl sulfoxide;
blank solution: a diluent;
test solution: taking 20mg of phthalimide potassium, precisely weighing, placing in a 25ml volumetric flask, dissolving and diluting to a scale with a diluent, and shaking up to obtain the phthalimide potassium.
Control solution: taking a proper amount of potassium hydrogen phthalate (about 20mg equivalent to phthalic acid), precisely weighing, placing in a 100ml volumetric flask, adding a diluent to dissolve and dilute to a scale, and shaking up. Precisely measuring 1.0ml, placing into a 50ml volumetric flask, adding a diluent to dilute to a scale, and shaking up to obtain the product.
(3) Assay method
Testing according to the above chromatographic conditions, sampling blank solution, control solution and sample solution respectively, and recording chromatogram.
And (5) judging a result: if a chromatographic peak consistent with the retention time of the potassium hydrogen phthalate exists in the chromatogram of the test solution, the content of the phthalic anhydride is obtained by subtracting the phthalic acid impurity and multiplying the product by a conversion factor of the phthalic acid and the phthalic anhydride of 0.89 according to the area normalization method.
(4) The result of the detection
A typical chromatogram is shown in FIG. 6. The results are shown in Table 3.
TABLE 3 test results of the test solutions
| Phthalic anhydride content | 0.00267％ |
Comparative example 1
(1) Chromatographic conditions
The instrument comprises the following steps: a high-efficiency liquidus chromatograph Agilent 1260;
a chromatographic column: agilent Infinity Lab Poroshell 120SB-AQ (4.6 mm. times.150 mm, 2.7 μm);
mobile phase: 0.01mol/L sodium dihydrogen phosphate (containing 0.1% triethylamine, pH adjusted by phosphoric acid 2.0) methanol 80:20 (v/v);
detection wavelength: 233 nm;
flow rate: 1.0 ml/min;
sample introduction amount: 10 mu l of the mixture;
column temperature: 25 ℃;
collecting time: and (3) 30 min.
(2) Solution preparation
Diluent agent: methanol;
blank solution: a diluent;
test solution: taking 20mg of phthalimide potassium, precisely weighing, placing in a 25ml volumetric flask, dissolving and diluting to a scale with a diluent, and shaking up to obtain the phthalimide potassium.
Control solution: taking a proper amount of potassium hydrogen phthalate (about 20mg equivalent to phthalic acid), precisely weighing, placing in a 100ml volumetric flask, adding a diluent to dissolve and dilute to a scale, and shaking up. Precisely measuring 1.0ml, placing into a 50ml volumetric flask, adding a diluent to dilute to a scale, and shaking up to obtain the product.
(3) Assay method
Testing according to the above chromatographic conditions, sampling blank solution, control solution and sample solution respectively, and recording chromatogram.
(4) The result of the detection
A typical chromatogram is shown in FIG. 7. From the chromatogram results, it was found that when the diluent in the chromatographic conditions was changed to methanol, both the main peak and the impurity peak had poor peak shapes, and had shoulder peaks, and the component to be measured underwent alcoholysis, resulting in a large new unknown impurity (retention time: 7.793 min).
The embodiment shows that the method provided by the invention is simple, convenient and quick, and has high accuracy, good repeatability and strong specificity. The method can accurately detect related substances in the phthalimide potassium salt, thereby effectively controlling the quality of the phthalimide potassium salt.
Claims (10)
1. A method for detecting related substances in phthalimide potassium salt is characterized by comprising the following steps: dissolving phthalimide potassium salt in a diluent by adopting a high performance liquid chromatography to prepare a phthalimide potassium solution, eluting by using an ultraviolet detector and any one of octadecylsilane chemically bonded silica, octylsilane chemically bonded silica or phenyl chemically bonded silica as a stationary phase and any one or a combination of a buffer salt solution and an organic solvent as a mobile phase, and recording a chromatogram; optionally, the mobile phase is a mixed solution of a buffered salt solution and an organic solvent.
2. The method of claim 1, wherein: the diluent is at least one selected from acetonitrile, tetrahydrofuran, 1, 4-dioxane, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, dimethyl sulfoxide, N-dimethylformamide and N, N-dimethylacetamide; optionally, the diluent is dimethyl sulfoxide.
3. The method according to claim 1 or 2, characterized in that: the stationary phase is any one of octadecyl silane bonded silica gel, octyl silane bonded silica gel or phenyl bonded silica gel modified by special side chain groups, and the particle size of the filler is 1.7-5 mu m; alternatively, the stationary phase is Agilent Infinity Lab Poroshell 120SB-AQ with a specification of 4.6mmx150mm and a filler particle size of 2.7 μm.
4. The method according to any one of claims 1 to 3, wherein: the mobile phase can also be added with a tail scavenging agent, and the tail scavenging agent is selected from any one of diethylamine and triethylamine or the combination thereof; optionally, the volume concentration of the tail-sweeping agent is 0.01-0.5%.
5. The method according to any one of claims 1 to 4, wherein: the pH value of the buffer salt solution is 0.5-5.0; preferably, the pH is 1.0-3.0; the pH of the buffered salt solution is adjusted using at least one selected from the group consisting of phosphoric acid, formic acid, acetic acid, perchloric acid, and trifluoroacetic acid.
6. The method according to any one of claims 1 to 5, wherein: the buffer salt solution is at least one of potassium dihydrogen phosphate, sodium dihydrogen phosphate, ammonium dihydrogen phosphate, dipotassium hydrogen phosphate, disodium hydrogen phosphate, diammonium hydrogen phosphate and ammonium acetate buffer solution; the concentration of the buffer salt solution is 0.001 mol/L-1.0 mol/L, preferably 0.005 mol/L-0.5 mol/L.
7. The method according to any one of claims 1 to 6, wherein: the organic solvent in the mobile phase is selected from at least one of alcohols, acetonitrile, amides and ketones; optionally, the organic solvent in the mobile phase is selected from at least one of methanol, ethanol, isopropanol, acetonitrile, formamide, and acetone; optionally, the organic solvent in the mobile phase is selected from at least one of methanol and acetonitrile.
8. The method according to any one of claims 1 to 7, wherein: the volume ratio of the buffer salt solution to the organic solvent in the mobile phase is 75-85: 15-25; optionally, the volume ratio of the buffered salt solution to the organic solvent in the mobile phase is 80: 20.
9. the method according to any one of claims 1 to 8, wherein: the sample injection amount of the detection method is 5-20 mul; the flow rate of the mobile phase is 0.5-1.5 ml/min; the column temperature of the stationary phase is 20-40 ℃, and preferably 20-30 ℃; the chromatogram is a chromatogram recorded at a detection wavelength of 200-230 nm; the concentration of the phthalimide potassium solution is 0.5mg/ml to 1.5 mg/ml;
optionally, the sample size of the detection method is 10 μ l; the flow rate of the mobile phase is 1.0 ml/min; the column temperature of the stationary phase is 25 ℃; the chromatogram is a chromatogram recorded at a detection wavelength of 233 nm; the concentration of the phthalimide potassium solution is 0.8mg/ml to 1.5 mg/ml.
10. The method according to any one of claims 1 to 9, wherein: the related substances are:
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| WO2011158249A1 (en) * | 2010-06-16 | 2011-12-22 | Glenmark Generics Limited | Process for preparation of milnacipran intermediate and its use in preparation of pure milnacipran |
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| US6066743A (en) * | 1999-05-07 | 2000-05-23 | General Electric Company | Solventless preparation of phthalimides |
| WO2011158249A1 (en) * | 2010-06-16 | 2011-12-22 | Glenmark Generics Limited | Process for preparation of milnacipran intermediate and its use in preparation of pure milnacipran |
| CN104955456A (en) * | 2013-01-28 | 2015-09-30 | H.隆德贝克有限公司 | N-substituted-5-substituted phthalamic acids as sortilin inhibitors |
| CN109020934A (en) * | 2018-07-30 | 2018-12-18 | 绍兴贝斯美化工股份有限公司 | The preparation method of intermediate containing halogenated benzene ring side chain fipronil bisamide structure |
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| 叶美君等: "固相萃取净化-气相色谱质谱法检测茶叶中邻苯二甲酰亚胺", 《中国茶叶加工》 * |
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