CN107941946A - A kind of detection method of Vonoprazan fumarate - Google Patents
A kind of detection method of Vonoprazan fumarate Download PDFInfo
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- CN107941946A CN107941946A CN201711187582.9A CN201711187582A CN107941946A CN 107941946 A CN107941946 A CN 107941946A CN 201711187582 A CN201711187582 A CN 201711187582A CN 107941946 A CN107941946 A CN 107941946A
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/26—Conditioning of the fluid carrier; Flow patterns
- G01N30/28—Control of physical parameters of the fluid carrier
- G01N30/34—Control of physical parameters of the fluid carrier of fluid composition, e.g. gradient
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
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Abstract
The invention discloses the detection method of Vonoprazan fumarate, it is detected using high performance liquid chromatograph, quantitative analysis is carried out using area normalization method, its chromatographic condition is as follows：Chromatographic column：Agilent ZORBAX SB‑phenyl；Sample size：5‑10μl；Flow velocity：0.8‑1.2ml/min；Column temperature：25‑35℃；Detection wavelength：250‑300nm；Mobile phase：0.1% aqueous formic acid of mobile phase A, Mobile phase B acetonitrile, its volume ratio are (5 70)：(30‑95)；Dilution：Acetonitrile:Water, its volume ratio are (40 60):50；Detector：UV detector；The detection method of the present invention can easy, accurate, quick, efficiently, reliably detect the purity and impurity of 5 (2 fluorophenyl) N methyl 1 (3 pyridyl sulfonyl) 1H pyrroles, 3 methylamine fumarate; with very high sensitivity; it is and easy to operate; it can realize and be kept completely separate, and then to study the basis that such compound provides research and development and quality testing.
Description
Technical field
The invention belongs to technical field of analytical chemistry, and in particular to a kind of detection method of Vonoprazan fumarate.
Background technology
Vonoprazan fumarate, its entitled 5- (2- fluorophenyls)-N- methyl isophthalic acids-(3- pyridyl sulfonyls) -1H- pyrrole of chemistry
- 3- methylamine fumarates are coughed up, are a kind of competitive sour retarding agents (P-CAB) of the potassium ion developed by Takeda Pharmaceutical Company Limited, in vitro
Experimental study shows that the ability that the compound suppresses proton pump is 400 times of Lansoprazole, it is relative to Na+,K+- ATPase's
Suppress selectivity more than 1000 times, can effective gastric acid secretion inhibiting, have the advantages that the duration is long.The purity of the compound
And the impurity contained will directly affect its acid suppression and treat the effect of gastric acid related disease.
At present, do not find that 5- (2- fluorophenyls)-N- methyl isophthalic acids-(3- pyridyl sulfonyls) -1H- pyrroles -3- methylamines are rich also
The pertinent literature and report of the method for detecting purity of horse hydrochlorate, in order to strengthen 5- (2- fluorophenyls)-N- methyl isophthalic acids-(3- pyridine radicals
Sulfonyl) -1H- pyrroles -3- methylamine fumarate quality controls are, it is necessary to develop its detection method.
The content of the invention
In view of the problems of the existing technology, the object of the present invention is to provide a kind of 5- (2- fluorophenyls)-N- methyl isophthalic acids-
The detection method of (3- pyridyl sulfonyls) -1H- pyrroles's -3- methylamine fumarates.
5- (2- fluorophenyls)-N- methyl isophthalic acids-(3- pyridyl sulfonyls) -1H- pyrroles's -3- methylamines fumarates (TAK-09)
Structural formula it is as follows：
5- (2- fluorophenyls) -1H- pyrroles -3- formaldehyde (TAK06) is 5- (2- fluorophenyls)-N- methyl isophthalic acids-(3- pyridine radicals sulphurs
Acyl group) -1H- pyrroles's -3- methylamines fumarates (TAK-09) intermediate, its structural formula is as follows：
To achieve these goals, the present invention uses following technical scheme：
A kind of Wo Nuolazan 5- (2- fluorophenyls)-N- methyl isophthalic acids-(3- pyridyl sulfonyls) -1H- pyrroles -3- methylamine richness horses
The detection method of hydrochlorate, comprises the following steps：
(1) 5- (2- fluorophenyls)-N- methyl isophthalic acids-(3- pyridyl sulfonyls) -1H- pyrroles -3- methylamine richness horses are weighed respectively
Hydrochlorate and 5- (2- fluorophenyls) -1H- pyrroles's -3- formaldehyde are placed in same volumetric flask, with dilution dissolving and constant volume, be configured to be
System compatibility test solution；Specifically, accurate 5- (2- fluorophenyls)-N- methyl isophthalic acids-(3- pyridine radicals sulphonyl for weighing 20-30mg
Base) -1H- pyrroles -3- methylamines fumarate and 20-30mg 5- (2- fluorophenyls) -1H- pyrroles's -3- formaldehyde be placed in it is same
In the volumetric flask of 50ml, with dilution dissolving and constant volume, system suitability test solution is configured to；Wherein, 5- (2- fluorophenyls)-
The concentration of N- methyl isophthalic acids-(3- pyridyl sulfonyls) -1H- pyrroles's -3- methylamine fumarates is 0.4-0.6mg/ml, 5- (2- fluorine
Phenyl) concentration of -1H- pyrroles's -3- formaldehyde is 0.4-0.6mg/ml；
(2) accurately weighed test sample, dissolve simultaneously constant volume with dilution, is configured to test solution；Specifically, it is accurate
The test sample of 25-50mg is weighed, is placed in the volumetric flask of 50ml, with dilution dissolve and constant volume, preparation obtains concentration and be
The test solution of 0.5-1mg/ml；
(3) it is accurate to measure dilution, liquid chromatograph is injected, gradient elution is carried out using mobile phase, and chromatogram is recorded,
There must not be interference；
(4) it is accurate to measure system suitability test solution, liquid chromatograph is injected, gradient elution is carried out using mobile phase,
And chromatogram is recorded, number of theoretical plate presses 5- (2- fluorophenyls)-N- methyl isophthalic acids-(3- pyridyl sulfonyls) -1H- pyrroles's -3- methylamines
Fumarate, which calculates, should be not less than 3000, and the separating degree between main peak and any impurity peaks should be not less than 1.5；
(5) it is accurate to measure test solution, liquid chromatograph is injected, gradient elution is carried out using mobile phase, and record color
Spectrogram, blank test chromatographic peak is deducted in the chromatogram of test solution, is calculated respectively by area normalization method；
The operating condition of wherein described high performance liquid chromatograph is：
Chromatographic column：Phenyl column；
Sample size：5-10μl；
Flow velocity：0.8-1.2ml/min；
Column temperature：25-35℃；
Detection wavelength：250-300nm；
Mobile phase：0.1% aqueous formic acid of mobile phase A:Mobile phase B acetonitrile, its volume ratio are (5-70)：(30-95)；
Dilution：Acetonitrile:Water, its volume ratio are (40-60):50；
Detector：UV detector.
Preferably, the chromatographic column is Agilent Zorbax SB phenyl, size 4.6*250mm, 5 μm.
Preferably, the sample size is 5 μ l.
Preferably, the flow velocity is 1ml/min.
Preferably, the Detection wavelength is 254nm.
Preferably, the column temperature is 30 DEG C.
Preferably, the dilution is acetonitrile and water is 50 by volume:50 mix.
Preferably, the condition of gradient elution is：0min：Mobile phase A 70%, Mobile phase B 30%；30min:Mobile phase
A5%, Mobile phase B 95%；30.01-35min：Mobile phase A 70%, Mobile phase B 30%.With 0.1% aqueous formic acid and second
Nitrile, as mobile phase, can improve separating effect, and improve peak type by appropriate concentration gradient.
Beneficial effects of the present invention
(1) detection method of the invention can realize 5- (2- fluorophenyls)-N- methyl isophthalic acids-(3- pyridyl sulfonyls) -1H-
The rapid and accurate determination of pyrroles's -3- methylamine fumarates, has very high sensitivity；
(2) detection method of the invention is easy to operate, and separating degree is not less than 1.5, meets the standard being kept completely separate；
(3) detection method of the invention for 5- (2- fluorophenyls)-N- methyl isophthalic acids-(3- pyridyl sulfonyls) -1H- pyrroles -
3- methylamine fumarates provide the basis of research and development and quality testing.
Brief description of the drawings
Fig. 1 is the high-efficient liquid phase chromatogram of test sample 1；
Fig. 2 is the high-efficient liquid phase chromatogram of test sample 2；
Fig. 3 is the high-efficient liquid phase chromatogram of test sample 3；
Fig. 4 is the high-efficient liquid phase chromatogram of test sample 4.
Embodiment
In order to preferably explain the present invention, it is described further in conjunction with specific examples below, but the present invention is unlimited
In specific embodiment.
Embodiment 1
A kind of inspection of 5- (2- fluorophenyls)-N- methyl isophthalic acids-(3- pyridyl sulfonyls) -1H- pyrroles's -3- methylamine fumarates
Survey method
First, instrument and testing conditions
Shimadzu LC-15C high performance liquid chromatographs, chromatographic column select Agilent ZORBAX SB-phenyl (4.6*
250mm,5μm)；
Sample size：5μl；
Flow velocity：1ml/min；
Column temperature：30℃；
Detection wavelength：254nm；
Mobile phase：0.1% aqueous formic acid of mobile phase A, Mobile phase B acetonitrile, using gradient elution, the gradient elution bar
Part is：0-30min：Mobile phase A 70%, Mobile phase B 30%；30-30.01min:Mobile phase A 5%, Mobile phase B 95%；
30.01-35min：Mobile phase A 70%, Mobile phase B 30%；
Dilution：Acetonitrile:Water, its volume ratio are (40-60):50；
Detector：UV detector.
2nd, experimental procedure
It is detected using high performance liquid chromatography, detecting step is as follows：
(1) respectively it is accurate weigh 25mg 5- (2- fluorophenyls)-N- methyl isophthalic acids-(3- pyridyl sulfonyls) -1H- pyrroles -
The 5- of 3- methylamines fumarate and 25mg (2- fluorophenyls) -1H- pyrroles's -3- formaldehyde is placed in the volumetric flask of same 50ml, is used
Dilution dissolving and constant volume, are configured to system suitability test solution；
(2) the accurate test sample for weighing 25mg, is placed in the volumetric flask of 50ml, dissolve simultaneously constant volume with dilution, matches somebody with somebody
The test solution that concentration is 0.5mg/ml is made；
(3) it is accurate to measure 5 μ l of dilution, liquid chromatograph is injected, gradient elution is carried out using mobile phase, and record chromatography
Figure；
(4) it is accurate to measure system suitability test solution μ l, liquid chromatograph is injected, carrying out gradient using mobile phase washes
It is de-, and chromatogram is recorded, number of theoretical plate presses 5- (2- fluorophenyls)-N- methyl isophthalic acids-(3- pyridyl sulfonyls) -1H- pyrroles's -3- first
Amine fumarate, which calculates, should be not less than 3000, and the separating degree between main peak and any impurity peaks should be not less than 1.5；
(5) it is accurate to measure 5 μ l of test solution, liquid chromatograph is injected, gradient elution is carried out using mobile phase, and record
Chromatogram, blank test chromatographic peak is deducted in the chromatogram of test solution, is calculated respectively by area normalization method.
Embodiment 2
Take 5- (2- fluorophenyls)-N- methyl isophthalic acids-(3- pyridyl sulfonyls) of four batches of same production specifications instruction production-
1H- pyrroles's -3- methylamine fumarate products, are respectively test sample 1-4, are detected according to the detection method of embodiment 1, are used
Area normalization method carries out purity and its impurity calculates, and testing result see the table below 1-4：
Table 1 is the testing result of test sample 1
Table 2 is the testing result of test sample 2
Table 3 is the testing result of test sample 3
Table 4 is the testing result of test sample 4
The detection method of the present invention can it is easy, accurate, quick, efficiently, reliably detect 5- (2- fluorophenyls)-N- first
The purity and impurity content of base -1- (3- pyridyl sulfonyls) -1H- pyrroles's -3- methylamine fumarates, have very high sensitive
Degree, it is and easy to operate, it is possible to achieve to be kept completely separate, and then research and development and quality testing are provided for the such compound of research
Basis.
The foregoing is merely the specific embodiment of the present invention, it is not intended to limit the scope of the invention, every utilization
The equivalent transformation that the present invention makees, is directly or indirectly used in other relevant technical fields, is similarly included in the present invention's
Among scope of patent protection.
Claims (10)
1. a kind of detection method of Vonoprazan fumarate, it is characterised in that comprise the following steps：
(1) 5- (2- fluorophenyls)-N- methyl isophthalic acids-(3- pyridyl sulfonyls) -1H- pyrroles's -3- methylamine fumarates are weighed respectively
It is placed in same volumetric flask with 5- (2- fluorophenyls) -1H- pyrroles's -3- formaldehyde, is fitted with dilution dissolving and constant volume, the system of being configured to
Answering property testing liquid；
(2) accurately weighed test sample, dissolve simultaneously constant volume with dilution, is configured to test solution；
(3) system suitability test solution, test solution and the blank sample are injected separately into high performance liquid chromatograph, adopted
Gradient elution is carried out with mobile phase, and records chromatographic peak；Wherein, blank sample is dilution；
The operating condition of wherein described high performance liquid chromatograph is：
Chromatographic column：Phenyl column；
Sample size：5-10μl；
Flow velocity：0.8-1.2ml/min；
Column temperature：25-35℃；
Detection wavelength：250-300nm；
Mobile phase：0.1% aqueous formic acid of mobile phase A:Mobile phase B acetonitrile, its volume ratio are (5-70):(30-95)；
Dilution：Acetonitrile:Water, its volume ratio are (40-60):50；
Detector：UV detector.
2. detection method according to claim 1, it is characterised in that in the system suitability test solution, 5- (2-
Fluorophenyl) concentration of-N- methyl isophthalic acids-(3- pyridyl sulfonyls) -1H- pyrroles's -3- methylamine fumarates is 0.4-0.6mg/ml,
The concentration of 5- (2- fluorophenyls) -1H- pyrroles's -3- formaldehyde is that concentration is 0.4-0.6mg/ml.
3. detection method according to claim 1, it is characterised in that the concentration of the test sample is 0.5-1mg/ml.
4. detection method according to claim 1, it is characterised in that the chromatographic column is Agilent Zorbax SB
Phenyl, size 4.6*250mm, 5 μm.
5. detection method according to claim 1, it is characterised in that the sample size is 5 μ l.
6. detection method according to claim 1, it is characterised in that the flow velocity is 1ml/min.
7. detection method according to claim 1, it is characterised in that the Detection wavelength is 254nm.
8. detection method according to claim 1, it is characterised in that the column temperature is 30 DEG C.
9. detection method according to claim 1, it is characterised in that the dilution is that acetonitrile is by volume with water
50:50 mix.
10. detection method according to claim 1, it is characterised in that the condition of gradient elution is：0min：Mobile phase A
70%, Mobile phase B 30%；30min:Mobile phase A 5%, Mobile phase B 95%；30.01-35min：Mobile phase A 70%, stream
Dynamic phase B 30%.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113390983A (en) * | 2021-05-26 | 2021-09-14 | 株洲千金药业股份有限公司 | Detection method for simultaneously determining 3 impurities in Voranolan fumarate |
| CN114487236A (en) * | 2022-01-26 | 2022-05-13 | 中山奕安泰医药科技有限公司 | Detection method of 2- [2- (2-fluorophenyl) -2-oxoethyl ] malononitrile |
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| CN105130955A (en) * | 2015-09-16 | 2015-12-09 | 海口南陆医药科技有限公司 | Preparation method of Vonoprazan fumarate |
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2017
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113390983A (en) * | 2021-05-26 | 2021-09-14 | 株洲千金药业股份有限公司 | Detection method for simultaneously determining 3 impurities in Voranolan fumarate |
| CN113390983B (en) * | 2021-05-26 | 2022-06-07 | 株洲千金药业股份有限公司 | Detection method for simultaneously determining 3 impurities in Voranolan fumarate |
| CN114487236A (en) * | 2022-01-26 | 2022-05-13 | 中山奕安泰医药科技有限公司 | Detection method of 2- [2- (2-fluorophenyl) -2-oxoethyl ] malononitrile |
| CN114487236B (en) * | 2022-01-26 | 2023-11-07 | 中山奕安泰医药科技有限公司 | Detection method of 2- [2- (2-fluorophenyl) -2-oxo-ethyl ] malononitrile |
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