CN117147730A - Liquid phase detection method for 6-cyano-2-naphthol and related substances thereof - Google Patents
Liquid phase detection method for 6-cyano-2-naphthol and related substances thereof Download PDFInfo
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- CN117147730A CN117147730A CN202311155422.1A CN202311155422A CN117147730A CN 117147730 A CN117147730 A CN 117147730A CN 202311155422 A CN202311155422 A CN 202311155422A CN 117147730 A CN117147730 A CN 117147730A
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- high performance
- performance liquid
- liquid chromatography
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- WKTNIBWKHNIPQR-UHFFFAOYSA-N 6-hydroxynaphthalene-2-carbonitrile Chemical compound C1=C(C#N)C=CC2=CC(O)=CC=C21 WKTNIBWKHNIPQR-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 238000001514 detection method Methods 0.000 title claims abstract description 16
- 239000000126 substance Substances 0.000 title claims abstract description 12
- 239000007791 liquid phase Substances 0.000 title abstract description 3
- 239000012535 impurity Substances 0.000 claims abstract description 39
- 238000000034 method Methods 0.000 claims abstract description 9
- 238000000926 separation method Methods 0.000 claims abstract description 7
- 239000000243 solution Substances 0.000 claims description 35
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 33
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 19
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- 238000007865 diluting Methods 0.000 claims description 13
- 239000007788 liquid Substances 0.000 claims description 11
- YTJSFYQNRXLOIC-UHFFFAOYSA-N octadecylsilane Chemical compound CCCCCCCCCCCCCCCCCC[SiH3] YTJSFYQNRXLOIC-UHFFFAOYSA-N 0.000 claims description 10
- 239000000377 silicon dioxide Substances 0.000 claims description 9
- 150000001875 compounds Chemical group 0.000 claims description 7
- REFMEZARFCPESH-UHFFFAOYSA-M sodium;heptane-1-sulfonate Chemical compound [Na+].CCCCCCCS([O-])(=O)=O REFMEZARFCPESH-UHFFFAOYSA-M 0.000 claims description 7
- 238000004090 dissolution Methods 0.000 claims description 6
- 238000010828 elution Methods 0.000 claims description 5
- 238000005303 weighing Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 238000002347 injection Methods 0.000 claims 1
- 239000007924 injection Substances 0.000 claims 1
- 238000012856 packing Methods 0.000 claims 1
- 230000035945 sensitivity Effects 0.000 abstract description 2
- 238000004811 liquid chromatography Methods 0.000 abstract 1
- 238000002203 pretreatment Methods 0.000 abstract 1
- 239000012071 phase Substances 0.000 description 16
- 239000013558 reference substance Substances 0.000 description 12
- 239000003643 water by type Substances 0.000 description 9
- 239000003814 drug Substances 0.000 description 7
- 229940079593 drug Drugs 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 4
- 239000011259 mixed solution Substances 0.000 description 4
- 239000012488 sample solution Substances 0.000 description 4
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 3
- 239000005695 Ammonium acetate Substances 0.000 description 3
- 229940043376 ammonium acetate Drugs 0.000 description 3
- 235000019257 ammonium acetate Nutrition 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- 239000012085 test solution Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 230000004807 localization Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 2
- 229940054967 vanquish Drugs 0.000 description 2
- HCBCJAFWOBCSRJ-UHFFFAOYSA-N (6-cyanonaphthalen-2-yl) trifluoromethanesulfonate Chemical compound C1=C(C#N)C=CC2=CC(OS(=O)(=O)C(F)(F)F)=CC=C21 HCBCJAFWOBCSRJ-UHFFFAOYSA-N 0.000 description 1
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 1
- KAUQJMHLAFIZDU-UHFFFAOYSA-N 6-Hydroxy-2-naphthoic acid Chemical compound C1=C(O)C=CC2=CC(C(=O)O)=CC=C21 KAUQJMHLAFIZDU-UHFFFAOYSA-N 0.000 description 1
- YLDFTMJPQJXGSS-UHFFFAOYSA-N 6-bromo-2-naphthol Chemical compound C1=C(Br)C=CC2=CC(O)=CC=C21 YLDFTMJPQJXGSS-UHFFFAOYSA-N 0.000 description 1
- PRYNJOJHKYNLIS-UHFFFAOYSA-N 6-hydroxynaphthalene-2-carbaldehyde Chemical compound C1=C(C=O)C=CC2=CC(O)=CC=C21 PRYNJOJHKYNLIS-UHFFFAOYSA-N 0.000 description 1
- ULKSSXOMKDEKPC-UHFFFAOYSA-N 6-hydroxynaphthalene-2-carboximidamide Chemical compound C1=C(O)C=CC2=CC(C(=N)N)=CC=C21 ULKSSXOMKDEKPC-UHFFFAOYSA-N 0.000 description 1
- SWEFYGCKCMJSPD-UHFFFAOYSA-N 6-methoxynaphthalene-2-carbonitrile Chemical compound C1=C(C#N)C=CC2=CC(OC)=CC=C21 SWEFYGCKCMJSPD-UHFFFAOYSA-N 0.000 description 1
- 241001251200 Agelas Species 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- MNZMMCVIXORAQL-UHFFFAOYSA-N naphthalene-2,6-diol Chemical compound C1=C(O)C=CC2=CC(O)=CC=C21 MNZMMCVIXORAQL-UHFFFAOYSA-N 0.000 description 1
- 239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000002753 trypsin inhibitor Substances 0.000 description 1
Classifications
-
- 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
-
- 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
- G01N2030/022—Column chromatography characterised by the kind of separation mechanism
- G01N2030/027—Liquid chromatography
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- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
Abstract
The invention discloses a detection method for separating and detecting 6-cyano-2-naphthol and related substances, belonging to the technical field of medical detection, wherein a specific sample pretreatment method is adopted to treat a sample to be detected, and a specific method liquid chromatography is adopted to carry out liquid phase detection, and the detection method comprises the following steps: the method can effectively separate and analyze and detect the 6-cyano-2-naphthol and the impurity 1 and the impurity 2 thereof, is convenient and simple, has high sensitivity and good separation degree, and has accurate result, and can be used for detecting related substances in the 6-cyano-2-naphthol.
Description
Technical Field
The invention belongs to the technical field of medicine detection, and relates to a detection method for separating and detecting 6-cyano-2-naphthol and related substances.
Background
6-cyano-2-naphthol, also known as 6-hydroxy-2-naphthol, of formula C 11 H 7 NO, molecular weight 169.18, CAS number 628-663-7, can be synthesized by a plurality of ways such as 6-hydroxy-2-naphthaldehyde, 6-methoxy-2-naphthalonitrile, 6-bromo-2-naphthol, and the like, the obtained way is simple and various, and the early phase of 6-cyano-2-naphthol is used as an extremely important liquid crystal compound intermediate, can be used for synthesizing dozens of liquid crystal compounds, and is widely used in photoelectric display devices. In recent years, the compound can be used as an intermediate for synthesizing protease and trypsin inhibitors, can be used for synthesizing various compounds such as 6-amidino-2-naphthol, 6-cyano-2-naphthyl trifluoro-methanesulfonate, 2-hydroxy-6-naphthoic acid and the like, and opens up new application in the pharmaceutical industry.
In the prior art, the detection methods for 6-cyano-2-naphthol are few, most of ammonium acetate systems are used as liquid crystal compound intermediates, the ammonium acetate systems are not stable enough, the problems of peak tailing or incomplete impurity separation and the like are easily caused, but the ammonium acetate systems are used as medical intermediates, and in order to further ensure the quality of medicines and the safety of prevention and medication, the method is developed, the impurities are controlled within the safety limit, and the quality of medicines is controllable. The research on the analysis method of the 6-cyano-2-naphthol has wide prospect, actively develops the analysis method, establishes strict quality standard, and has great significance for guaranteeing the safe production of medicines.
Disclosure of Invention
Aiming at the technical problems, the invention provides a simple, convenient and efficient high performance liquid chromatography which is applicable to 6-cyano-2-naphthol and related substances thereof, wherein a chromatographic column stationary phase is an octadecylsilane chemically bonded silica chromatographic column, a mobile phase consists of a phase A and a phase B, the phase A is sodium heptanesulfonate solution, the phase B is acetonitrile and is eluted according to a gradient program, and the high performance liquid chromatography is provided with an ultraviolet detector.
In a preferred embodiment of the present invention, the octadecyl silane chemically bonded silica column is commercially available, preferably an octadecyl silane chemically bonded silica column manufactured by Thermofishier, waters, agilent, kromasil, agela company, preferably a series manufactured by Thermofishier, waters, more preferably Waters.
In a preferred embodiment of the present invention, the octadecylsilane chemically bonded silica column is selected from one of Kromasi1 100-5-C18, YMC Triat C18, phenomenex kinetex C, titank C18 ES-C18, epicC18, ZORBAXSB-C18, ZORBAX 300SB-C18, XDB-C18, waters XB ridge C18, venusil HLPC C18, venusil C18 Plus, venusil MP C18, agilentMicrosphere C18, thermofishier Hypersil GOLD C, or a combination thereof.
In the preferred technical scheme of the invention, the octadecylsilane chemically bonded silica chromatographic column is preferably any one of Waters XBiridge C18 and Thermofishier Hypersil GOLD C.
In the preferred embodiment of the invention, the preferred embodiment of the octadecylsilane chemically bonded silica chromatographic column is Waters XBiridge C18.6 mm multiplied by 250mm,5 μm.
In a preferred embodiment of the present invention, the column temperature of the chromatographic column is 35-45 ℃, preferably 37-43 ℃, more preferably 39-41 ℃.
In a preferred embodiment of the present invention, the sample preparation solvent is a mixed solution of acetonitrile and water, preferably acetonitrile/water (V: V) =15:85, and more preferably acetonitrile/water (V: V) =20:80.
In the preferred technical scheme of the invention, the mobile phase A is sodium heptanesulfonate solution, and the preparation method is to weigh 6.07g of 1-sodium heptanesulfonate, add 6ml of acetic acid after adding a proper amount of water for dissolution, and dilute to 1000ml with water.
In a preferred embodiment of the present invention, the flow rate of the mobile phase is 0.8ml/min to 1.2ml/min, preferably 0.9ml/min to 1.1ml/min, and more preferably 1.0ml/min.
In a preferred embodiment of the present invention, the detection wavelength of the ultraviolet detector is 245nm to 265nm, preferably 250nm to 260nm, and more preferably 254nm.
In a preferred embodiment of the present invention, the sample volume is 5. Mu.l to 10. Mu.l, preferably 5. Mu.l.
In a preferred embodiment of the present invention, the relevant substance is selected from any one of impurity 1 and impurity 2 or a combination thereof.
In the preferred technical scheme of the invention, the impurity peak-out sequence of the related substances is impurity 2, 6-cyano-2-naphthol and impurity 1 in sequence, and the separation degree of the peaks of adjacent compounds is more than 1.5.
In a preferred embodiment of the present invention, the high performance liquid chromatography comprises an eluted sample, wherein the eluted sample comprises any one or a combination of a positioning solution, a sample solution and a separation degree solution.
In a preferred embodiment of the invention, the concentration of the positioning solution is between 10. Mu.g/ml and 500. Mu.g/ml, preferably between 20. Mu.g/ml and 500. Mu.g/ml, more preferably 500. Mu.g/ml.
In a preferred embodiment of the present invention, the concentration of the sample solution is 0.2mg/ml to 1mg/ml, preferably 0.4mg/ml to 0.8mg/ml, more preferably 0.5mg/ml.
In a preferred technical scheme of the invention, the high performance liquid chromatography comprises the following steps:
1) Preparing a solution:
solvent: acetonitrile/water (V: V) =20:80
Positioning solution: taking a proper amount of impurity 1 and impurity 2 reference substances, dissolving the reference substances by using a solvent, and diluting the reference substances to prepare single positioning solution with the concentration of 500 mug/ml.
Mixing the separation degree solution: taking a proper amount of impurity 1, impurity 2 and 6-cyano-2-naphthol reference substances, dissolving and diluting with a solvent to prepare a mixed solution sample solution with the concentration of the impurity 1, the impurity 2 of 25 mug/ml and the concentration of the 6-cyano-2-naphthol of 0.5 mg/ml: and dissolving a proper amount of 6-cyano-2-naphthol in a solvent and diluting to prepare a test solution with the concentration of 0.5mg/ml.
2) Chromatographic conditions:
binding the gel with octadecyl silane chemically on a column Waters XBiridge C18, 250mm×4.6mm,5 μm; taking sodium heptanesulfonate solution (weighing 6.07g of 1-sodium heptanesulfonate, adding a proper amount of water for dissolution, then adding 6ml of acetic acid, and diluting to 1000ml with water) as a mobile phase A; acetonitrile is taken as a mobile phase B, the flow rate is 1.0ml per minute, linear gradient elution is carried out, and the detection wavelength is 254nm; column temperature 40 ℃. Precisely measuring 5 μl of the sample solution, injecting into a liquid chromatograph, and recording the chromatogram.
Drawings
FIG. 1 is a high performance liquid chromatogram of impurity 1 localization;
FIG. 2 is a high performance liquid chromatogram of impurity 2 localization;
FIG. 3 is a high performance liquid chromatogram of a mixed resolution solution;
FIG. 4 is a high performance liquid chromatogram of 6-cyano-2-naphthol test detection;
FIG. 5 is a high performance liquid chromatogram of 6-cyano-2-naphthol test sample detection.
Detailed Description
The following description will be given in detail of preferred examples of the present invention, in which the test methods under specific conditions not specified are generally conventional, and the described examples are only a part of examples of the present invention, but not all examples can be better described, and based on the examples in the present invention, those skilled in the art can make insubstantial modifications and adjustments to the embodiments, which are within the scope of the protection of the present invention.
Example 1
Instrument and high performance liquid chromatography conditions:
high performance liquid chromatograph: thermo Vanquish Core high performance liquid chromatography systems and workstations;
chromatographic column: waters XBiridge C18, (250 mm 4.6mm,5 μm) octadecylsilane chemically bonded silica column;
mobile phase: taking sodium heptanesulfonate solution (weighing 6.07g of 1-sodium heptanesulfonate, adding a proper amount of water for dissolution, then adding 6ml of acetic acid, and diluting to 1000ml with water) as a mobile phase A; acetonitrile as mobile phase B
Elution procedure:
detection wavelength: 254nm;
flow rate: 1.0ml/min
Column temperature 40 ℃.
The experimental steps are as follows:
and taking a proper amount of the impurity 1 reference substance, dissolving the reference substance into a solution of 0.5mg/ml by using a solvent, and diluting the solution to serve as an impurity 1 positioning solution.
And taking a proper amount of impurity 2 reference substance, dissolving the reference substance into a solution of 0.5mg/ml by using a solvent, and diluting the solution to serve as an impurity 2 positioning solution.
Dissolving 6-cyano-2-naphthol reference with solvent, adding impurity 1 and impurity 2 locating solution, diluting to obtain mixed solution of 6-cyano-2-naphthol 0.5mg/ml, and mixing impurity 1 and impurity 2 25 μg/ml to obtain mixed resolution solution.
A proper amount of 6-cyano-2-naphthol is taken, dissolved by a solvent and diluted into a solution of 0.5mg/ml to be used as a test solution.
Removing 5 μl of each of the above solutions, injecting into a liquid chromatograph, and recording the chromatogram.
Example 2
Instrument and high performance liquid chromatography conditions:
high performance liquid chromatograph: thermo Vanquish Core high performance liquid chromatography systems and workstations;
chromatographic column: waters XBiridge C18, (250 mm 4.6mm,5 μm) octadecylsilane chemically bonded silica column;
mobile phase: taking sodium heptanesulfonate solution (weighing 6.07g of 1-sodium heptanesulfonate, adding a proper amount of water for dissolution, then adding 6ml of acetic acid, and diluting to 1000ml with water) as a mobile phase A; acetonitrile was used as mobile phase B.
Elution procedure:
detection wavelength: 254nm;
flow rate: 1.0ml/min
Column temperature 40 ℃.
The experimental steps are as follows:
and taking a proper amount of the impurity 1 reference substance, dissolving the reference substance into a solution of 0.5mg/ml by using a solvent, and diluting the solution to serve as an impurity 1 positioning solution.
And taking a proper amount of impurity 2 reference substance, dissolving the reference substance into a solution of 0.5mg/ml by using a solvent, and diluting the solution to serve as an impurity 2 positioning solution.
Dissolving 6-cyano-2-naphthol reference with solvent, adding impurity 1 and impurity 2 locating solution, diluting to obtain mixed solution of 6-cyano-2-naphthol 0.5mg/ml, and mixing impurity 1 and impurity 2 25 μg/ml to obtain mixed resolution solution.
A proper amount of 6-cyano-2-naphthol is taken, dissolved by a solvent and diluted into a solution of 0.5mg/ml to be used as a test solution.
Taking 5 μl of each of the above solutions, injecting into a liquid chromatograph, and recording the chromatogram.
The results show that the impurity 1, the impurity 2 and the 6-cyano-2-naphthol can be effectively detected by adopting the methods of the embodiments 1 and 2, the separation degree among the related substances impurity 1, the impurity 2 and the 6-cyano-2-naphthol is better than 1.5, the sensitivity of the method is better, the theoretical plate number of the 6-cyano-2-naphthol peak is more than 10000, the product quality can be effectively controlled, the potential medication risk is eliminated, and the safety of the medicine quality is ensured.
While the invention has been described in terms of preferred embodiments, it will be understood by those skilled in the art that various changes and modifications can be made without departing from the spirit and scope of the invention.
Claims (11)
1. A detection method for separating and detecting 6-cyano-2-naphthol and related substances is characterized in that: the high performance liquid chromatograph is adopted, and the chromatographic conditions are as follows:
packing of chromatographic column, octadecylsilane chemically bonded silica chromatographic column;
an ultraviolet detector;
column temperature is 35-45 ℃;
preparing a solvent, namely mixing acetonitrile and water;
the flow rate is 0.8ml/min-1.2ml/min;
the mobile phase is that sodium heptanesulfonate solution is used as mobile phase A; acetonitrile is taken as a mobile phase B;
the elution condition is 0-60 min, the A phase/B phase ratio is from high to low gradient condition;
the method is used for detecting and analyzing 6-cyano-2-naphthol and related substances;
wherein,
the structure of 6-cyano-2-naphthol is as follows:
the structural formula of the related substances is as follows:
2. the high performance liquid chromatography according to claim 1, wherein: the preparation method of the sodium heptanesulfonate solution comprises the steps of weighing 6.07g of 1-sodium heptanesulfonate, adding a proper amount of water for dissolution, adding 6ml of acetic acid, and diluting to 1000ml with water.
3. The high performance liquid chromatography according to claim 1, wherein the elution procedure is as follows:
4. the high performance liquid chromatography according to claim 1, wherein: the sample injection volume is 5-10. Mu.l.
5. The high performance liquid chromatography according to claim 1, wherein: the wavelength of the ultraviolet detector is 245nm-265nm.
6. The high performance liquid chromatography according to claim 1, wherein: the grain diameter of the chromatographic column is less than or equal to 5 mu m, and the column length is 150 mm-250 mm.
7. The high performance liquid chromatography according to claim 1, wherein: the solvent used for sample dissolution was acetonitrile to water (V: V) =20:80.
8. The high performance liquid chromatography according to claim 1, wherein: the sample is dissolved by ultrasonic vibration.
9. The high performance liquid chromatography according to claim 1, wherein: the flow rate is 0.8ml/min-1.2ml/min.
10. The high performance liquid chromatography according to claim 1, wherein: the degree of separation between impurity 1 and impurity 2 and the chromatographic peak of the adjacent compound is greater than 1.5.
11. The high performance liquid chromatography according to claim 1, wherein: the theoretical plate number of the peak area of the 6-cyano-2-naphthol is more than 10000.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202311155422.1A CN117147730A (en) | 2023-09-08 | 2023-09-08 | Liquid phase detection method for 6-cyano-2-naphthol and related substances thereof |
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| Application Number | Priority Date | Filing Date | Title |
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| CN202311155422.1A CN117147730A (en) | 2023-09-08 | 2023-09-08 | Liquid phase detection method for 6-cyano-2-naphthol and related substances thereof |
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