CN109725074A - A kind of method of separating and assaying of related substance contained by loxoprofen acid and its salt - Google Patents
A kind of method of separating and assaying of related substance contained by loxoprofen acid and its salt Download PDFInfo
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- CN109725074A CN109725074A CN201811536895.5A CN201811536895A CN109725074A CN 109725074 A CN109725074 A CN 109725074A CN 201811536895 A CN201811536895 A CN 201811536895A CN 109725074 A CN109725074 A CN 109725074A
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Abstract
The present invention provides a kind of method of separating and assaying of related substance contained by loxoprofen acid and its salt, include the following steps: that separation detection will be carried out in loxoprofen acid and its salt sample injection liquid chromatograph；Wherein, the chromatographic column of the liquid chromatograph is C8-C18 column, and mobile phase is that water phase-organic phase mixes in certain proportion.This method may be implemented quantitative and qualitatively measure related substance contained in loxoprofen acid and its salt, to effectively control the quality of loxoprofen acid and its salt, quality monitoring more effectively is realized to loxoprofen acid and its product salt, there is actual directive significance to the quality for improving Related product, furthermore this method specificity is strong, accuracy is high, easy to operate, should be widely promoted and is applied.
Description
Technical field
The present invention relates to loxoprofen acid and its salt quality control field, in particular to a kind of loxoprofen acid and
The method of separating and assaying of related substance contained by its salt.
Background technique
Loxoprofen acid and its salt for treat rheumatoid arthritis, Osteoarthritis, Lumbago, the periarthritis of shoulderjoint,
Neck shoulder wrist syndrome, toothache anti-inflammatory and analgesia, operation after, after wound and extraction after analgesia and anti-inflammatory, acute upper respiratory tract
Scorching antipyretic and anti-inflammatory.The most common are loxoprofen sodium, entitled 2- [4- (the 2- oxo rings penta of chemistry in loxoprofen and its salt
Alkane -1- ylmethyl) phenyl] sodium propionate dihydrate, molecular formula C15H17NaO3.2H2O.Loxoprofen sodium structural formula are as follows:
During synthesizing the compound, the intermediate for having several steps important may influence medicine due to removing not exclusively
The purity and quality of object；Degradation impurity is generated in the production of drug or storage, no therapeutic effect or influence drug
Stability and curative effect, or even be detrimental to health, the synthesis and degradation for loxoprofen and its salt mainly control related
Substance has 5, is respectively: brufen related impurities, brufen impurity K, loxoprofen's open loop impurity, loxoprofen's related impurities
4 and loxoprofen's related impurities 3, structural formula is respectively as follows:
For the degradation impurity during the related substance introduced during synthesis loxoprofen sodium and storage, in bulk pharmaceutical chemicals
In need to carry out quality control, therefore, loxoprofen sodium and its separation in relation to substance are realized, in the conjunction of loxoprofen sodium
Have great importance at the quality controlling party face with storage process, but at present in terms of quality monitoring, in the prior art one
There is not relatively effective method directly.
In view of this, the present invention is specifically proposed.
Summary of the invention
The purpose of the present invention is to provide the method for separating and assaying of related substance contained by a kind of loxoprofen acid and its salt,
The method of separating and assaying may be implemented quantitative and qualitatively measure related substance contained in loxoprofen acid and its salt, thus
The quality of effective control loxoprofen acid and its salt, more effectively realizes quality monitoring to loxoprofen acid and its product salt,
The purity for guaranteeing loxoprofen acid and its salt Related product has actual directive significance to the quality for improving Related product, furthermore
This method specificity is strong, and accuracy is high, easy to operate, should be widely promoted and is applied.
In order to realize above-mentioned purpose of the invention, the following technical scheme is adopted:
The embodiment of the invention provides a kind of method of separating and assaying of related substance contained by loxoprofen acid and its salt, packets
Include following steps:
Separation detection will be carried out in loxoprofen acid and its salt sample solution injection liquid chromatograph；
Wherein, the chromatographic column of the liquid chromatograph is C8-C18 column or T3 column, and mobile phase is the mixed of water phase and organic phase
Close object.
The present invention provides a kind of using liquid chromatograph to realize the quality monitoring of loxoprofen acid and its product salt
To the method that related substance contained in loxoprofen acid and its salt drug or its preparation carries out separation determination, measured by groping
Concrete operations parameter during method is realized to the drug and its effective quality testing of preparation, provides one kind very
Effective monitoring method also provides the technology path that can refer to subsequent operation.
Preferably, the solvent in loxoprofen acid and its salt sample solution is methanol, mobile phase or diluent, described
Diluent is the mixture of water phase and organic phase；
Preferably, loxoprofen acid and its salt be loxoprofen acid metal salt, it is any in loxoprofen acid ammonium salt
One or two kinds of mixing.
Preferably as further enforceable mode, the organic phase is methanol, acetonitrile, propyl alcohol, isopropanol, tetrahydro
The mixing of any one or more in furans, it is therefore preferable to methanol and acetonitrile, more preferably methanol.
Preferably as further enforceable mode, the water phase is water and triethylamine, diethylamine, glacial acetic acid, acetic acid
The mixing of any one or more in ammonium, acetate, it is therefore preferable to triethylamine and glacial acetic acid, more preferably glacial acetic acid.
In the method for separating and assaying, mobile phase and diluent are collectively constituted by inorganic phase and water phase, loxoprofen
Acid and its salt sample can form sample solution, used chromatographic column using methanol, diluent or flowing phase dilution dissolution
Preferably C18 column or T3 column, good separating effect, optimal selection T3 column.
Preferably as further enforceable mode, in the loxoprofen acid and its salt sample solution of above-mentioned formation, Lip river
The concentration of rope ketoprofen acid and its salt is 0.1-3mg/ml, is more preferably 2mg/ml.
Preferably as further enforceable mode, the flow velocity of mobile phase is between 0.5-2.0ml/min, more preferably
For 1.0ml/min.
Preferably as further enforceable mode, the Detection wavelength of liquid chromatograph is between 200-250nm, column
Temperature is between 20-40 DEG C.
More preferably, the best detection wavelength of liquid chromatograph is 235nm, and column oven optimum temperature is 35 DEG C.
Preferably as further enforceable mode, the sampling volume of loxoprofen acid and its salt sample solution is 10-
Between 30 μ L, it is therefore preferable to 20 μ L.
Preferably as further enforceable mode, in the diluent, organic phase is methanol, and water phase is water, ice second
Acid, triethylamine mixing, wherein water, glacial acetic acid, triethylamine volume ratio be (900-1100): (1-2): (1-2), organic phase with
The volume ratio of water phase is (30-50): (50-70)；
Preferably, water, glacial acetic acid, triethylamine volume ratio be 1000:2:1；
Preferably, the volume ratio of organic phase and water phase is 40:60.
Preferably as further enforceable mode, in the mobile phase, organic phase is methanol, and water phase is water, ice second
Acid, triethylamine mixing, wherein water, glacial acetic acid, triethylamine volume ratio be (900-1100): (1-2): between (1-2)；
Preferably, water, glacial acetic acid, triethylamine volume ratio be 1000:1:1.
Preferably as further enforceable mode, liquid chromatogram uses gradient elution program, gradient elution program
Are as follows:
In < 18min, the volume ratio of organic phase and water phase is (40-41): (59-60)；
In > 18min, the volume ratio of organic phase and water phase is (50-75): (25-50)；
In > 55min, the volume ratio of organic phase and water phase is (40-41): (59-60).
The model of high performance liquid chromatograph of the invention, has no special requirements, and the chromatograph that the present invention uses is Waters:
2695+2998(PDA)。
The above-mentioned specific method of separating and assaying of the present invention, when practical operation, can be realized as follows:
1) take loxoprofen acid and its salt or containing loxoprofen acid and its salt formulation samples it is appropriate, with methanol, mobile phase
Or dilution sample dissolution, it is configured to the sample solution of every 1mL acid containing loxoprofen 0.1-3mg.
2) setting flow rate of mobile phase is 0.5-2.0mL/min, and flow rate of mobile phase is preferably 1.0mL/min, and Detection wavelength is
200~250nm, best detection wavelength 235nm, column oven temperature are 20-50 DEG C, most preferably 30 DEG C of column oven temperature.
3) sample solution 10-50 μ L 1) is taken, liquid chromatograph is injected, completes loxoprofen acid and its salt and related substance
Separation determination, in which: the model of high performance liquid chromatograph has no special requirements, the chromatograph model Waters:2695 of use
+2998(PDA)。
A specific liquid chromatogram operating method is given below:
Sample preparation: loxoprofen acid and its salt sample are dissolved using diluent, concentration 2mg/ml；
Diluent: methanol: [water: triethylamine: glacial acetic acid=1000:1:2]=400:600；
Chromatographic column: T3 (4.6 × 250mm, 5 μm)；
Flow velocity: 1.0ml/min；
Detection wavelength: 235nm；
Column temperature: 30 DEG C；
Sample volume: 20 μ l；
Mobile phase: water phase: water: triethylamine: glacial acetic acid (1000:1:1) organic phase: methanol, specific elution program see the table below
1。
1 gradient elution program of table
The present invention can efficiently separate loxoprofen acid and its related substance of salt, solve by using T3 chromatographic column
Loxoprofen acid and its salt and the separation determination problem in relation to substance ensure that the matter of loxoprofen acid and its salt bulk drug
Amount is controllable.
Compared with prior art, the invention has the benefit that
(1) method of separating and assaying of related substance contained by of the invention loxoprofen acid and its salt, the separation determination side
Method may be implemented quantitative and qualitatively measure related substance contained in loxoprofen acid and its salt, to effectively control Lip river
The quality of rope ketoprofen acid and its salt more effectively realizes quality monitoring to loxoprofen acid and its product salt, produces to correlation is improved
The quality of product has actual directive significance, furthermore；
(2) the method for separating and assaying specificity of related substance contained by of the invention loxoprofen acid and its salt is strong, accurately
Degree is high, easy to operate, should be widely promoted and is applied, can create more extensive economic benefit.
Detailed description of the invention
It, below will be to specific in order to illustrate more clearly of the specific embodiment of the invention or technical solution in the prior art
Embodiment or attached drawing needed to be used in the description of the prior art be briefly described, it should be apparent that, it is described below
Attached drawing is some embodiments of the present invention, for those of ordinary skill in the art, before not making the creative labor
It puts, is also possible to obtain other drawings based on these drawings.
Fig. 1 is the loxoprofen sodium of the embodiment of the present invention 1 and its HPLC figure in relation to substance；
Fig. 2 is the loxoprofen sodium of the embodiment of the present invention 2 and its HPLC figure in relation to substance；
Fig. 3-5 is the loxoprofen sodium and its related substance HPLC figure of the embodiment of the present invention 3；
Fig. 6 is the HPLC figure of the blank solvent of the embodiment of the present invention 3；
Fig. 7 is the loxoprofen sodium and its related substance HPLC figure of the embodiment of the present invention 4；
Fig. 8 is the HPLC figure of the blank solvent of the embodiment of the present invention 4.
Specific embodiment
Embodiment of the present invention is described in detail below in conjunction with embodiment, but those skilled in the art will
Understand, the following example is merely to illustrate the present invention, and is not construed as limiting the scope of the invention.It is not specified in embodiment specific
Condition person carries out according to conventional conditions or manufacturer's recommended conditions.Reagents or instruments used without specified manufacturer is
The conventional products that can be obtained by commercially available purchase.
Embodiment 1
Specific method of separating and assaying operates progress in accordance with the following steps:
Sample preparation: loxoprofen acid and its salt sample are using diluent dissolution, concentration 2mg/ml, and by loxoprofen
In acid and its salt sample injection liquid chromatograph；
Diluent: methanol: [water: triethylamine: glacial acetic acid=1000:1:1]=40:60；
Chromatographic column: T3 (4.6 × 250mm, 5 μm)；
Flow velocity: 0.5ml/min；
Detection wavelength: 200nm；
Column temperature: 20 DEG C；
Sample volume: 10 μ l；
Mobile phase: water phase: water: triethylamine: glacial acetic acid (900:1:1) organic phase: methanol, specific elution program see the table below 2.
2 gradient elution program of table
The present invention can efficiently separate loxoprofen acid and its related substance of salt, by above-mentioned by using T3 chromatographic column
Condition carries out efficient liquid phase chromatographic analysis, records chromatogram, and the results are shown in attached figure 1, the chromatographic peak that retention time is 41.081 in Fig. 1
For loxoprofen sodium, remaining chromatographic peak is each impurity peaks of loxoprofen sodium.
Embodiment 2
Specific method of separating and assaying operates progress in accordance with the following steps:
Sample preparation: loxoprofen acid and its salt sample are using diluent dissolution, concentration 0.5mg/ml, and by Luo Suoluo
In fragrant acid and its salt sample injection liquid chromatograph；
Diluent: methanol: [water: triethylamine: glacial acetic acid=1100:1:2]=50:50；
Chromatographic column: T3 (4.6 × 250mm, 5 μm)；
Flow velocity: 1.0ml/min；
Detection wavelength: 250nm；
Column temperature: 40 DEG C；
Sample volume: 30 μ l；
Mobile phase: water phase: water: triethylamine: glacial acetic acid (1100:2:1) organic phase: methanol, specific elution program see the table below
3。
3 gradient elution program of table
The present invention can efficiently separate loxoprofen acid and its related substance of salt, by above-mentioned by using T3 chromatographic column
Condition carries out efficient liquid phase chromatographic analysis, records chromatogram, and the results are shown in attached figure 2, the chromatographic peak that retention time is 34.146 in Fig. 2
For loxoprofen sodium, remaining chromatographic peak is each impurity peaks of loxoprofen sodium.
Embodiment 3
Specific method of separating and assaying operates progress in accordance with the following steps:
Sample preparation: loxoprofen acid and its salt sample are using diluent dissolution, concentration 3mg/ml, and by loxoprofen
In acid and its salt sample injection liquid chromatograph；
Diluent: methanol: [water: triethylamine: glacial acetic acid=900:1:1]=30:70；
Chromatographic column: T3 (4.6 × 250mm, 5 μm)；
Flow velocity: 2.0ml/min；
Detection wavelength: 235nm；
Column temperature: 25 DEG C；
Sample volume: 20 μ l；
Mobile phase: water phase: water: triethylamine: glacial acetic acid (1000:1:2) organic phase: methanol, specific elution program see the table below
4。
4 gradient elution program of table
The present invention can efficiently separate loxoprofen acid and its related substance of salt, by above-mentioned by using T3 chromatographic column
Condition carries out efficient liquid phase chromatographic analysis, and 3 samples record chromatogram, and the result of chromatogram is respectively referring to Fig. 3-5, in Fig. 3
The chromatographic peak that retention time is 35.055min is loxoprofen sodium, remaining chromatographic peak is each impurity peaks of loxoprofen sodium.In Fig. 4,
The chromatographic peak that retention time is 35.052min is loxoprofen sodium, it can be seen that loxoprofen sodium and its impurity under this condition
It can be kept completely separate, the chromatographic peak that retention time is 34.443min in Fig. 5 is loxoprofen sodium, it can be seen that under this condition
Loxoprofen sodium can be kept completely separate with its impurity.Although the retention time of each sample may be somewhat different, of the invention
Method of separating and assaying may be implemented to be kept completely separate, Fig. 6 be without containing sample when blank reagent liquid chromatogram, for
The chromatogram of above-mentioned Fig. 3-5 compares to use.
Embodiment 4
Specific method of separating and assaying operates progress in accordance with the following steps:
Sample preparation: loxoprofen acid and its salt sample are dissolved using methanol, concentration 1mg/ml, and loxoprofen is sour
And its in salt sample injection liquid chromatograph；
Chromatographic column: Thermo, BDS HYPERSIL C8,4.6 × 250mm, 5 μm；
Flow velocity: 1.0ml/min；
Detection wavelength: 235nm；
Column temperature: 30 DEG C；
Sample volume: 20 μ l；
Mobile phase: water phase: water: triethylamine: glacial acetic acid (1000:1:2) organic phase: methanol, specific elution program see the table below
4。
5 gradient elution program of table
The present invention can efficiently separate loxoprofen acid and its related substance of salt, by above-mentioned by using C8 chromatographic column
Condition carry out efficient liquid phase chromatographic analysis, record chromatogram, the results are shown in attached figure 7-8, Fig. 7 in retention time be 25.158 chromatography
Peak is loxoprofen sodium, remaining chromatographic peak is each impurity peaks of loxoprofen sodium, the liquid phase of blank reagent when Fig. 8 is without containing sample
Chromatogram.
Although illustrate and describing the present invention with specific embodiment, it will be appreciated that without departing substantially from of the invention
Many other change and modification can be made in the case where spirit and scope.It is, therefore, intended that in the following claims
Including belonging to all such changes and modifications in the scope of the invention.
Claims (10)
1. a kind of method of separating and assaying of related substance contained by loxoprofen acid and its salt, which is characterized in that including walking as follows
It is rapid:
Separation detection will be carried out in loxoprofen acid and its salt sample solution injection liquid chromatograph；
Wherein, the chromatographic column of the liquid chromatograph is C8-C18 column or T3 column, and mobile phase is the mixture of water phase and organic phase；
Preferably, the solvent in loxoprofen acid and its salt sample solution is methanol, mobile phase or diluent, the dilution
Agent is the mixture of water phase and organic phase；
Preferably, loxoprofen acid and its salt are loxoprofen acid metal salt, any one in loxoprofen acid ammonium salt
Or two kinds of mixing.
2. method of separating and assaying according to claim 1, which is characterized in that the organic phase be methanol, acetonitrile, propyl alcohol,
The mixing of any one or more in isopropanol, tetrahydrofuran, it is therefore preferable to methanol and acetonitrile, more preferably methanol.
3. method of separating and assaying according to claim 1, which is characterized in that the water phase be water and triethylamine, diethylamine,
Glacial acetic acid, ammonium acetate, the mixing of any one or more in acetate, it is therefore preferable to triethylamine and glacial acetic acid, more preferably
Glacial acetic acid.
4. method of separating and assaying according to claim 1, which is characterized in that the loxoprofen acid and its salt sample solution
In, the concentration of loxoprofen acid and its salt is 0.1-3mg/ml.
5. method of separating and assaying according to claim 1, which is characterized in that the flow velocity of mobile phase is 0.5-2.0ml/min
Between, it is more preferably 1.0ml/min.
6. method of separating and assaying according to claim 1, which is characterized in that the Detection wavelength of liquid chromatograph is 200-
Between 250nm, column temperature is between 20-40 DEG C.
7. method of separating and assaying according to claim 1, which is characterized in that loxoprofen acid and its salt sample solution into
Sample volume is between 10-30 μ L, it is therefore preferable to 20 μ L.
8. method of separating and assaying according to claim 1, which is characterized in that in the diluent, organic phase is methanol, water
The mixing of Xiang Weishui, glacial acetic acid, triethylamine, wherein water, glacial acetic acid, triethylamine volume ratio be (900-1100): (1-2): (1-
2), the volume ratio of organic phase and water phase is (30-50): (50-70)；
Preferably, water, glacial acetic acid, triethylamine volume ratio be 1000:2:1；
Preferably, the volume ratio of organic phase and water phase is 40:60.
9. method of separating and assaying according to claim 1, which is characterized in that in the mobile phase, organic phase is methanol, water
The mixing of Xiang Weishui, glacial acetic acid, triethylamine, wherein water, glacial acetic acid, triethylamine volume ratio be (900-1100): (1-2): (1-
2) between；
Preferably, water, glacial acetic acid, triethylamine volume ratio be 1000:1:1.
10. -9 described in any item method of separating and assaying according to claim 1, which is characterized in that liquid chromatogram is washed using gradient
De- program, gradient elution program are as follows:
In < 18min, the volume ratio of organic phase and water phase is (40-41): (59-60)；
In > 18min, the volume ratio of organic phase and water phase is (50-75): (25-50)；
In > 55min, the volume ratio of organic phase and water phase is (40-41): (59-60).
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| CN110261531A (en) * | 2019-07-27 | 2019-09-20 | 湖南九典制药股份有限公司 | Detection method in relation to substance in a kind of loxoprofen or its sodium salt |
| CN115236255A (en) * | 2022-08-04 | 2022-10-25 | 迪沙药业集团有限公司 | Method for detecting loxoprofen sodium related substances |
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| CN110261531A (en) * | 2019-07-27 | 2019-09-20 | 湖南九典制药股份有限公司 | Detection method in relation to substance in a kind of loxoprofen or its sodium salt |
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| CN115236255A (en) * | 2022-08-04 | 2022-10-25 | 迪沙药业集团有限公司 | Method for detecting loxoprofen sodium related substances |
| CN115236255B (en) * | 2022-08-04 | 2023-08-25 | 迪沙药业集团有限公司 | Method for detecting related substances of loxoprofen sodium |
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| CN109725074B (en) | 2021-07-13 |
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