CN114965791A - Method for determining residues in plerixafor by headspace gas chromatography - Google Patents
Method for determining residues in plerixafor by headspace gas chromatography Download PDFInfo
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- CN114965791A CN114965791A CN202210667823.4A CN202210667823A CN114965791A CN 114965791 A CN114965791 A CN 114965791A CN 202210667823 A CN202210667823 A CN 202210667823A CN 114965791 A CN114965791 A CN 114965791A
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- diisopropylethylamine
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- 238000000034 method Methods 0.000 title claims abstract description 23
- 238000003988 headspace gas chromatography Methods 0.000 title claims abstract description 12
- YIQPUIGJQJDJOS-UHFFFAOYSA-N plerixafor Chemical compound C=1C=C(CN2CCNCCCNCCNCCC2)C=CC=1CN1CCCNCCNCCCNCC1 YIQPUIGJQJDJOS-UHFFFAOYSA-N 0.000 title claims description 24
- 229960002169 plerixafor Drugs 0.000 title claims description 24
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims abstract description 82
- 239000000523 sample Substances 0.000 claims abstract description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 13
- 238000002347 injection Methods 0.000 claims abstract description 9
- 239000007924 injection Substances 0.000 claims abstract description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 8
- 239000012488 sample solution Substances 0.000 claims abstract description 8
- 239000012159 carrier gas Substances 0.000 claims abstract description 5
- 230000035945 sensitivity Effects 0.000 claims abstract description 4
- 239000012085 test solution Substances 0.000 claims abstract description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 28
- 239000000243 solution Substances 0.000 claims description 20
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 11
- 239000010453 quartz Substances 0.000 claims description 10
- 239000013558 reference substance Substances 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 7
- 239000011248 coating agent Substances 0.000 claims description 5
- 238000000576 coating method Methods 0.000 claims description 5
- 239000007789 gas Substances 0.000 claims description 5
- 239000011261 inert gas Substances 0.000 claims description 4
- 238000004587 chromatography analysis Methods 0.000 claims description 3
- 238000001514 detection method Methods 0.000 claims description 3
- 238000007865 diluting Methods 0.000 claims description 3
- 229910052734 helium Inorganic materials 0.000 claims description 3
- 239000001307 helium Substances 0.000 claims description 3
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 238000005259 measurement Methods 0.000 claims description 2
- 239000012224 working solution Substances 0.000 abstract description 7
- 238000012360 testing method Methods 0.000 abstract description 5
- 238000011084 recovery Methods 0.000 abstract description 4
- 239000002904 solvent Substances 0.000 abstract description 4
- 238000010812 external standard method Methods 0.000 abstract description 2
- 238000000926 separation method Methods 0.000 abstract description 2
- WOOWBQQQJXZGIE-UHFFFAOYSA-N n-ethyl-n-propan-2-ylpropan-2-amine Chemical compound CCN(C(C)C)C(C)C.CCN(C(C)C)C(C)C WOOWBQQQJXZGIE-UHFFFAOYSA-N 0.000 abstract 1
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 description 5
- 206010035226 Plasma cell myeloma Diseases 0.000 description 5
- 102000004269 Granulocyte Colony-Stimulating Factor Human genes 0.000 description 4
- 108010017080 Granulocyte Colony-Stimulating Factor Proteins 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 210000003958 hematopoietic stem cell Anatomy 0.000 description 3
- 201000000050 myeloid neoplasm Diseases 0.000 description 3
- 239000011550 stock solution Substances 0.000 description 3
- 238000002054 transplantation Methods 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- 208000034578 Multiple myelomas Diseases 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000012088 reference solution Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 102000019034 Chemokines Human genes 0.000 description 1
- 108010012236 Chemokines Proteins 0.000 description 1
- 206010025323 Lymphomas Diseases 0.000 description 1
- 239000002576 chemokine receptor CXCR4 antagonist Substances 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000005220 pharmaceutical analysis Methods 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
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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
-
- 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
- G01N30/04—Preparation or injection of sample to be analysed
- G01N30/06—Preparation
-
- 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
- G01N30/62—Detectors specially adapted therefor
- G01N30/64—Electrical detectors
- G01N30/68—Flame ionisation detectors
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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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)
- Investigating Or Analysing Biological Materials (AREA)
Abstract
The invention discloses a headspace gas chromatography method for determining residue in plerixaforN,N-a process for diisopropylethylamine comprising: getN,NAn appropriate amount of diisopropylethylamine (diisopropylethylamine) diluted with a solvent (DMSO) to 1mLN,N-diisopropylethylamine 0.025mg of a working solution, and the same solvent is used to prepare plexafor with a concentration of 25mg/mL as a test solution; the initial temperature of the column incubator is 40 DEG.C o C, temperature programming 15 o C is increased to 240/min o C, keeping for 2 min; at the FID detector 260 o C, the temperature of the sample inlet is 200 DEG o C, detecting under chromatographic conditions that the split ratio is 5:1 and the carrier gas is nitrogen, taking the sample solution and the working solution, placing the sample solution and the working solution into a sample injection bottle, injecting the sample, and recording the colorAnd (4) calculating a spectrogram by an external standard method. The method has the characteristics of good separation degree of the measured result, simplicity, rapidness, strong specificity, high sensitivity and the like. The method is linear (Y =71398.8817X +4241.1206, R) 2 = 0.9979), sample recovery was 106%. It is suitable for measuring residue in plerixaforN,NDiisopropylethylamine limits test.
Description
The technical field is as follows:
the invention relates to a method for determining residual N, N-diisopropylethylamine in plerixafor by using a headspace gas chromatography, belonging to the technical field of pharmaceutical analysis.
Background art:
plexafor chemical name: 1,1' - [1, 4-benzenedi (methylene) ] di-1, 4,8, 11-tetraazacyclotetradecane.
The chemical structural formula is as follows:
plerixafor, a chemokine CXCR4 receptor antagonist developed by american Genzyme (purchased by cenofiranta france), was first marketed in the united states on day 12 and 15 of 2008 for use in combination with granulocyte colony-stimulating factor (G-CSF) to promote hematopoietic stem cells into the bloodstream of non-hodgkin's lymphoma (NHL) and Multiple Myeloma (MM) patients for collection, followed by autologous transplantation; subsequently marketed in the european union 7 months in 2009 for combined administration with granulocyte colony-stimulating factor (G-CSF) to promote hematopoietic stem cells into the bloodstream of lymphoma and Multiple Myeloma (MM) patients for collection, followed by autologous transplantation; marketed in japan at 12 months of 2016 for the promotion of hematopoietic stem cells into the patient's bloodstream for collection, followed by autologous transplantation. At present, the product is not on the market at home, the original research injection is reported (NHL, 2018Q2 batch), 3 raw materials and injection (chemical drugs 3.1 types) are imitated at home and approved clinically (Jiangsu Osaikang pharmaceutical industry, national medicine one-heart pharmaceutical industry, Hunan Wuzhou Tong pharmaceutical industry), pharmacokinetics and verification clinical of the national medicine one-heart and Hunan Wuzhou Tong are being recruited, indications are NHL, NHL + MM respectively, and the original research batch is planned to be produced with 4 types of imitated drugs after delivery.
The invention content is as follows:
the invention aims to provide a method for determining residual N, N-diisopropylethylamine in plerixafor by using a headspace gas chromatography, which can be used for testing the residual N, N-diisopropylethylamine in the plerixafor, so that the residual N, N-diisopropylethylamine meets the limit requirement, and the quality of the plerixafor is ensured.
A method for measuring residual N, N-diisopropylethylamine in plerixafor by using a headspace gas chromatography is characterized in that a quartz capillary chromatographic column is selected, inert gas is used as a gas source, the column adopts a programmed heating mode, a shunting mode and an FID detector, wherein the inert gas can select nitrogen or helium, the length of the quartz capillary chromatographic column is 30-60 m, the column diameter is 0.25-0.53 mm, the coating thickness is 0.25-3 um, and when the carrier gas source is nitrogen, the programmed heating condition is as follows: the initial temperature is 40-60 ℃, the heating rate is 10-30 ℃, the final temperature is 200-280 ℃, the holding time is 1-10 min, and the linear velocity is 15-50 cm/s. The headspace temperature is 80-150 ℃, and the shaking time is 15-60 minutes.
In some embodiments of the invention, the quartz capillary chromatography column has a length of 30-60 m, a column diameter of 0.25-0.53 mm, and a coating thickness of 0.25-3 um. Wherein the quartz capillary chromatography column preferably has a length of 30m, a column diameter of preferably 0.32mm, and a coating thickness of preferably 3 um.
In some embodiments of the invention, the carrier gas source is nitrogen or helium, preferably nitrogen.
In some embodiments of the invention, the conditions of temperature programming are: the initial temperature is 40-60 ℃, the preferred temperature is 40 ℃, the heating rate is 10-30 ℃, the preferred temperature is 15 ℃, the final temperature is 200-280 ℃, the preferred temperature is 260 ℃, the maintaining time is 1-10 min, the preferred time is 2min, and the linear velocity is 15-50 cm/s, the preferred time is 30 cm/s.
In some embodiments of the invention, the headspace temperature is 80 to 150 ℃, preferably 110 ℃, and the shaking time is 15 to 60 minutes, preferably 45 minutes.
In some embodiments of the invention, the injection inlet temperature is 180 ℃ to 250 ℃, preferably 200 ℃, and the injection is performed in a split ratio manner, preferably a split ratio of 5: 1.
Furthermore, the invention provides a method for measuring residual N, N-diisopropylethylamine in plerixafor by using a headspace gas chromatography, which comprises the following steps:
(1) taking a proper amount of plerixafor, dissolving the plerixafor by dimethyl sulfoxide (DMSO), and then fixing the volume by dimethyl sulfoxide to prepare a sample solution with the concentration of the plerixafor being 25 mg/mL;
(2) taking a proper amount of N, N-diisopropylethylamine, dissolving with dimethyl sulfoxide (DMSO), and then diluting to constant volume with dimethyl sulfoxide to prepare a reference substance solution with the concentration of the N, N-diisopropylethylamine of 0.025 mg/mL;
(3) taking an N, N-diisopropylethylamine reference substance solution and a plerixafor test substance solution, determining residual N, N-diisopropylethylamine in the plerixafor by adopting a headspace gas chromatography, adjusting the detection sensitivity to ensure that the peak height of the N, N-diisopropylethylamine in the reference substance solution is obvious, and if the peak area of the N, N-diisopropylethylamine at the position of the N, N-diisopropylethylamine working substance solution is not greater than the peak area of the peak position of the N, N-diisopropylethylamine working substance solution in the plerixafor test substance solution, adopting a quartz capillary column as a chromatographic column for determination, wherein the initial temperature of the column temperature is 40 ℃, the programmed temperature rise is 15 ℃/mL, and the temperature rise is 240 ℃ and is kept for 2 min; the sample inlet temperature is 200 ℃, the split ratio is 5:1, the linear velocity is 30cm/s, an FID detector is adopted, the detector temperature is 260 ℃, 1mL of the N, N-diisopropylethylamine reference substance solution and the plerixafor sample solution are respectively taken and placed into a headspace bottle, a cover is pressed, the headspace bottle is placed into a headspace sample injector, the headspace temperature is set to be 110 ℃, the shaking time is 45 minutes, and the sample injection is carried out according to the method.
The method has the characteristics of good separation degree, simplicity, rapidness, strong specificity, high sensitivity and the like. The method has good linearity (Y is 71398.8817X +4241.1206, R 2 0.9979), the recovery from loading was 106%. The method is suitable for detecting the limit of the residual N, N-diisopropylethylamine in the plerixafor.
Description of the drawings:
FIG. 1 gas chromatogram of N, N-diisopropylethylamine reference solution.
FIG. 2 gas chromatogram of the reference solution of N, N-diisopropylethylamine added to the solution of Plexafor test sample.
FIG. 3 gas chromatogram of the sample solution of Plexafor.
The specific implementation mode is as follows:
in order to make the objects, technical solutions and advantages of the present method more apparent, the present invention is further described in detail with reference to the following embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and do not limit the invention.
The following description is made in detail for the purpose of illustrating the principles of the present invention.
The method for determining the residual N, N-diisopropylethylamine in the plerixafor by the headspace gas chromatography comprises the following steps:
s101: an appropriate amount of N, N-diisopropylethylamine was diluted with a solvent (DMSO) to give a control solution containing 0.025mg of N, N-diisopropylethylamine per 1 mL. Accurately weighing a proper amount of sample, and diluting the sample into a solution of 25mg of sample in each 1mL by using a solvent (DMSO), namely the test solution.
S102: taking quartz capillary column (30m 0.53mm 3.0um, fixing solution is 6% cyanopropylbenzene-94% dimethyl polysiloxane) as chromatographic column for determination, and keeping the column temperature at the initial temperature of 40 ℃ and at the rate of 15 ℃ per minute to 240 ℃ for 2 min;
s103: detecting under chromatographic conditions that an FID detector is 260 ℃, the temperature of a sample inlet is 200 ℃, the split ratio is 5:1 and carrier gas is nitrogen, putting 1mL of sample solution and working solution into a sample injection bottle, the headspace temperature is 110, the shaking time is 45 minutes, injecting the sample, recording a chromatogram, and calculating by an external standard method.
The application of the principle of the invention will be further illustrated with reference to the following examples.
(1) Linear survey
Taking a proper amount of N, N-diisopropylethylamine, precisely weighing, preparing a stock solution containing about 2500ug of N, N-diisopropylethylamine in every 1mL by using the solution to obtain a stock solution A, and accurately weighing the stock solution A to be respectively diluted into standard solutions with the concentrations of 0.0125mg/mL, 0.02 mg/mL, 0.03mg/mL and 0.0375 mg/mL. 1uL of sample was injected and the peak area was recorded. Linear regression is carried out by using the peak area (Y) and the concentration (X) of the N, N-diisopropylethylamine, and the result shows that the N, N-diisopropylethylamine has a good linear relation with the peak area of the N, N-diisopropylethylamine within the concentration range of 12.5-37.5 mg/mL. 71398.8817X +4241.1206, R 2 ＝0.9979。
(2) Repeatability of
And (3) continuously feeding a working solution into a six-needle sample, and inspecting the repeatability of the method according to the peak area of N, N-diisopropylethylamine in the working solution. The RSD of the repeated measurement is 8.4 percent, which meets the requirement.
(3) Recovery rate of sample
3 samples of the same lot were accurately weighed and prepared with a working solution (25ug/mL) to give a solution of Plexafor a concentration of about 25mg/mL, and the results are shown in the following table.
Sample recovery rate of N, N-diisopropylethylamine
(4) Detection limit
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications made within the spirit and principle of the present invention are intended to be covered by the scope of the present application.
Claims (4)
1. A method for measuring residual N, N-diisopropylethylamine in plerixafor by using a headspace gas chromatography is characterized in that a quartz capillary chromatographic column is selected, inert gas is used as a gas source, the column adopts a programmed heating mode, a shunting mode and an FID detector, wherein the inert gas can select nitrogen or helium, the length of the quartz capillary chromatographic column is 30-60 m, the column diameter is 0.25-0.53 mm, the coating thickness is 0.25-3 um, and when the carrier gas source is nitrogen, the programmed heating condition is as follows: the initial temperature is 40-60 ℃, the heating rate is 10-30 ℃, the final temperature is 200-280 ℃, the holding time is 1-10 min, and the linear velocity is 15-50 cm/s. The headspace temperature is 80-150 ℃, the shaking time is 15-60 minutes, and the injection inlet temperature is 180-250 ℃.
2. The method of claim 1, wherein the quartz capillary chromatography column has a length of 30m, a column diameter of 0.32mm, and a coating thickness of 3 um; the method of claim 1, wherein the temperature programming is: the initial temperature was 40 deg.C, the rate of temperature rise was 15 deg.C/min, the final temperature was 240 deg.C, and was maintained for 2 min.
3. The method of claim 1, split mode, split ratio of 5: 1.
4. A method for measuring residual N, N-diisopropylethylamine in plerixafor by using a headspace gas chromatography is characterized by comprising the following steps:
(1) taking a proper amount of plexafor, dissolving the plexafor by dimethyl sulfoxide (DMSO), and then fixing the volume by dimethyl sulfoxide to prepare a sample solution with the plexafor concentration of 25 mg/mL;
(2) taking a proper amount of N, N-diisopropylethylamine, dissolving with dimethyl sulfoxide (DMSO), and then diluting to constant volume with dimethyl sulfoxide to prepare a reference substance solution with the concentration of the N, N-diisopropylethylamine of 0.025 mg/mL;
(3) taking an N, N-diisopropylethylamine reference substance solution and a plerixafor test solution, measuring residual N, N-diisopropylethylamine in the plerixafor by adopting a headspace gas chromatography, adjusting the detection sensitivity to ensure that the peak height of the N, N-diisopropylethylamine in the reference substance solution is obvious, and if the N, N-diisopropylethylamine has a peak at the position in the plerixafor test solution, the peak area of the peak is not larger than that of the N, N-diisopropylethylamine working substance solution, wherein a quartz capillary column is adopted as a chromatographic column for measurement, the initial temperature of the column is 40 ℃, the programmed temperature is 15 ℃/mL, the temperature is increased to 240 ℃, and the temperature is kept for 2 min; the sample inlet temperature is 200 ℃, the split ratio is 5:1, the linear velocity is 30cm/s, an FID detector is adopted, the detector temperature is 260 ℃, 1mL of the N, N-diisopropylethylamine reference substance solution and the plerixafor sample solution are respectively taken and placed into a headspace bottle, a cover is pressed, the headspace bottle is placed into a headspace sample injector, the headspace temperature is set to be 110 ℃, the shaking time is 45 minutes, and the sample injection is carried out according to the method.
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| Title |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116500172A (en) * | 2023-06-29 | 2023-07-28 | 成都普康唯新生物科技有限公司 | Detection method of amine solvent in acidic substrate |
| CN116500172B (en) * | 2023-06-29 | 2023-09-05 | 成都普康唯新生物科技有限公司 | Detection method of amine solvent in acidic substrate |
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