CN116735756A - Detection method for measuring 3-bromopropylamine hydrobromide impurity in peama Bei Teqi starting material by gas chromatography - Google Patents
Detection method for measuring 3-bromopropylamine hydrobromide impurity in peama Bei Teqi starting material by gas chromatography Download PDFInfo
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- CN116735756A CN116735756A CN202310986358.5A CN202310986358A CN116735756A CN 116735756 A CN116735756 A CN 116735756A CN 202310986358 A CN202310986358 A CN 202310986358A CN 116735756 A CN116735756 A CN 116735756A
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- 239000012535 impurity Substances 0.000 title claims abstract description 39
- PQIYSSSTRHVOBW-UHFFFAOYSA-N 3-bromopropan-1-amine;hydron;bromide Chemical compound Br.NCCCBr PQIYSSSTRHVOBW-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 239000007858 starting material Substances 0.000 title claims abstract description 19
- 238000001514 detection method Methods 0.000 title claims abstract description 18
- 238000004817 gas chromatography Methods 0.000 title claims abstract description 17
- 239000000243 solution Substances 0.000 claims abstract description 63
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 33
- 239000012488 sample solution Substances 0.000 claims abstract description 22
- 239000000523 sample Substances 0.000 claims abstract description 21
- 239000013558 reference substance Substances 0.000 claims abstract description 13
- 239000003960 organic solvent Substances 0.000 claims abstract description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 17
- 239000011550 stock solution Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 238000004090 dissolution Methods 0.000 claims description 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 6
- 239000012159 carrier gas Substances 0.000 claims description 6
- 239000007789 gas Substances 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 4
- 239000011259 mixed solution Substances 0.000 claims description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 4
- 230000000630 rising effect Effects 0.000 claims description 4
- 238000002347 injection Methods 0.000 claims 1
- 239000007924 injection Substances 0.000 claims 1
- ZTGQZSKPSJUEBU-UHFFFAOYSA-N 3-bromopropan-1-amine Chemical compound NCCCBr ZTGQZSKPSJUEBU-UHFFFAOYSA-N 0.000 abstract description 2
- 230000009286 beneficial effect Effects 0.000 abstract description 2
- 238000000926 separation method Methods 0.000 abstract description 2
- 238000010812 external standard method Methods 0.000 abstract 1
- 239000012088 reference solution Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 9
- 239000003814 drug Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- 230000035945 sensitivity Effects 0.000 description 5
- NCGAPYLHHZMWPI-UHFFFAOYSA-N 3-(4-methoxyphenoxy)propan-1-amine Chemical compound COC1=CC=C(OCCCN)C=C1 NCGAPYLHHZMWPI-UHFFFAOYSA-N 0.000 description 4
- 229940079593 drug Drugs 0.000 description 3
- YMTINGFKWWXKFG-UHFFFAOYSA-N fenofibrate Chemical compound C1=CC(OC(C)(C)C(=O)OC(C)C)=CC=C1C(=O)C1=CC=C(Cl)C=C1 YMTINGFKWWXKFG-UHFFFAOYSA-N 0.000 description 3
- 229960002297 fenofibrate Drugs 0.000 description 3
- 102000023984 PPAR alpha Human genes 0.000 description 2
- 239000008186 active pharmaceutical agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000012490 blank solution Substances 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 229940088679 drug related substance Drugs 0.000 description 2
- 108091008725 peroxisome proliferator-activated receptors alpha Proteins 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 2
- 206010067484 Adverse reaction Diseases 0.000 description 1
- 108010023302 HDL Cholesterol Proteins 0.000 description 1
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 1
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 description 1
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000006838 adverse reaction Effects 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000219 mutagenic Toxicity 0.000 description 1
- 230000003505 mutagenic effect Effects 0.000 description 1
- 238000003908 quality control method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
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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
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- 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 detection method for detecting 3-bromopropylamine hydrobromide impurities in a peama Bei Teqi starting material by a gas chromatography. Comprising the following steps: a. preparing a reference substance solution; b. preparing a sample solution; c. preparing a sample adding solution; d. setting parameters of a gas chromatograph; e. performing gas chromatography detection; and then obtaining a map, judging whether 3-bromopropylamine hydrobromide impurities exist according to the map of the sample solution and the reference solution, and calculating the content of the 3-bromopropylamine hydrobromide impurities in the sample solution by adopting an external standard method. The beneficial effects of the invention are as follows: the 3-bromopropylamine hydrobromide is converted into 3-bromopropylamine by sodium hydroxide solution, and then extracted by an organic solvent, so that the aim of separation and detection by adopting a gas chromatography is fulfilled.
Description
Technical Field
The invention belongs to the technical field of medicine analysis, and particularly relates to a detection method for detecting 3-bromopropylamine hydrobromide impurities in a peama Bei Teqi starting material by a gas chromatography.
Background
Pematite is an important drug for lowering triglyceride, and plays roles of lowering triglyceride and raising high-density lipoprotein cholesterol (good cholesterol) by activating peroxisome proliferator-activated receptor (PPARα), and belongs to a novel PPRA alpha agonist. The product is marketed in japan in 2018, and accumulated sales in 2021 become more than fenofibrate tablets, and the product is a marketable drug for replacing fenofibrate in japan. Meanwhile, the safety is better, the clinical application range is wide, and the adverse reaction rate is only 60% of that of fenofibrate. Lower safety as a high selection of PPAR-alpha doses and therefore may be used in combination with statins.
The structural formula of the bemate bulk drug is as follows:
。
3- (4-methoxyphenoxy) propylamine is a key starting material for synthesis of pemfibrate, 3-bromopropylamine hydrobromide is a key material for formation of 3- (4-methoxyphenoxy) propylamine, and the impurity is a potentially mutagenic impurity which, if removed incompletely, will be introduced into the end product of the drug substance, thereby affecting the purity and quality of the drug substance. Therefore, the residual quantity of the 3-bromopropylamine hydrobromide in the product needs to be strictly controlled, so that the establishment of a research method with high sensitivity and high accuracy is very important.
The structural formulas of 3- (4-methoxyphenoxy) propylamine and 3-bromopropylamine hydrobromide are as follows:
(3- (4-methoxyphenoxy) propylamine);
(3-Bromopropylamine hydrobromide).
Because the 3-bromopropylamine hydrobromide has no ultraviolet absorption, the conventional high performance liquid chromatography cannot meet the detection requirement; meanwhile, because the boiling point of the liquid is higher, the detection purpose is difficult to realize by directly adopting a gas chromatography method.
Disclosure of Invention
In order to solve the problems, the invention provides a method which comprises the steps of firstly adopting alkaline solution to pretreat 3-bromopropylamine hydrobromide, then using organic solvent to extract to obtain free 3-bromopropylamine, and then adopting gas chromatography to detect, wherein the method has good specificity and accuracy and high sensitivity, and realizes the detection of the residual quantity of 3-bromopropylamine hydrobromide in the initial material of peama Bei Teqi.
In order to achieve the purpose, the invention adopts the following technical scheme that the detection method for detecting the 3-bromopropylamine hydrobromide impurity in the starting material of the pemadzuki Bei Teqi by using a gas chromatography method comprises the following steps.
a. Taking a proper amount of 3-bromopropylamine hydrobromide, adding 0.1mol/L sodium hydroxide solution for dissolution, and preparing a solution containing 0.01mg/ml of the product as an impurity stock solution; and (3) taking a proper amount of impurity stock solution, adding an organic solvent with the same volume, fully and uniformly mixing, shaking, standing, and taking an upper layer solution as a reference substance solution.
b. And (3) taking a proper amount of a peama Bei Teqi starting material, adding a certain volume of 0.1mol/L sodium hydroxide solution for dissolution to prepare a solution containing 10mg per 1ml, adding an organic solvent with the same volume, fully and uniformly mixing, shaking, standing, and taking an upper layer solution as a sample solution.
c. And (3) taking a proper amount of a peama Bei Teqi initial material, adding a proper amount of an impurity stock solution for dissolving, preparing a mixed solution containing 10mg/ml of the product and 0.01mg/ml of the impurity, adding an organic solvent with the same volume, fully and uniformly mixing, shaking, standing, and taking an upper layer solution as a sample adding solution.
d. Setting gas chromatograph parameters, the temperature of a sample inlet is 270-290 ℃, the flow rate of carrier gas is 0.8-1.2 ml/min, the temperature rising program is 95-105 ℃ and maintained for 1-3 min, the temperature rising speed is 10-20 ℃ per minute to 300 ℃ and maintained for 4-6 min, the temperature of a detector is 280-300 ℃, and the split ratio is 10:1-20:1.
e. And d, respectively carrying out gas chromatography detection on the reference substance solution, the sample solution and the sample adding solution under the condition of the step d, then obtaining a map, judging whether 3-bromopropylamine hydrobromide impurity exists according to the sample solution map and the sample adding, and comparing the sample solution map with the reference substance solution map to obtain the content of the 3-bromopropylamine hydrobromide in the sample solution.
Preferably, the organic solvent in the steps a, b and c is one or more of n-hexane, n-heptane, dichloromethane or ethyl acetate.
Preferably, in the step e, the feed amount of the system applicability solution, the test sample solution and the control solution is 1. Mu.l to 3. Mu.l.
Preferably, in step d, the chromatographic column is Agilent CP-Sil 8CB for Amines (30 m×0.32mm,1.00 μm), the sample inlet temperature is 280 ℃, the carrier gas flow rate is 1ml/min, the temperature raising program is the initial temperature of 100 ℃, the temperature is maintained for 2min, the temperature raising speed of 20 ℃ per minute is up to 300 ℃, the temperature is maintained for 5min, the detector temperature is 300 ℃, and the split ratio is 10:1.
The beneficial effects of the invention are as follows: the invention provides a detection method for detecting 3-bromopropylamine hydrobromide impurities in a peama Bei Teqi starting material by a gas chromatography, which selects a special pretreatment mode to convert the 3-bromopropylamine hydrobromide into a free form, thereby realizing the detection purpose of the gas chromatography. The method selects the capillary column as the amino column, is suitable for detecting amino substances, can achieve good peak type and sensitivity, can be used for quantitatively detecting the 3-bromopropylamine hydrobromide in Yu Peima Bei Teqi starting materials, and has important significance in the aspects of medicine quality control and medicine safety.
Drawings
FIG. 1 is a chromatogram of a hollow white solution of example 1.
FIG. 2 is a chromatogram of the control solution in example 1.
FIG. 3 is a chromatogram of the sample solution in example 1.
FIG. 4 is a chromatogram of the loading solution of example 1.
Detailed Description
The invention is described in further detail below with reference to the drawings to enable those skilled in the art to practice the same and to refer to the description.
Example 1.
a. And (3) adding an appropriate amount of 0.1mol/L sodium hydroxide solution into an equal volume of ethyl acetate, fully and uniformly mixing, shaking, standing, and taking the upper layer solution as a blank solution.
b. Taking a proper amount of 3-bromopropylamine hydrobromide, adding 0.1mol/L sodium hydroxide solution for dissolution, and preparing a solution containing 0.01mg/ml of the product as an impurity stock solution; and (3) taking a proper amount of impurity stock solution, adding ethyl acetate with the same volume, fully and uniformly mixing, shaking, standing, and taking an upper layer solution as a reference substance solution.
c. And (3) taking a proper amount of a peama Bei Teqi starting material, adding a certain volume of 0.1mol/L sodium hydroxide solution for dissolution to prepare a solution containing 10mg per 1ml, adding an equal volume of ethyl acetate, fully and uniformly mixing, shaking, standing, and taking an upper layer solution as a sample solution.
d. And (3) taking a proper amount of a peama Bei Teqi initial material, adding a proper amount of an impurity stock solution for dissolving, preparing a mixed solution containing 10mg/ml of the product and 0.01mg/ml of the impurity, adding ethyl acetate with the same volume, fully and uniformly mixing, shaking, standing, and taking an upper layer solution as a sample adding solution.
e. The parameters of the gas chromatograph are set, the chromatographic column is Agilent CP-Sil 8CB for Amines (30 m multiplied by 0.32mm,1.00 mu m), the temperature of the sample inlet is 280 ℃, the flow rate of carrier gas is 1ml/min, the temperature raising program is the initial temperature of 100 ℃, the temperature is maintained for 2min, the temperature raising speed of 20 ℃ per minute is up to 300 ℃, the temperature is maintained for 5min, the detector temperature is 300 ℃, and the split ratio is 10:1.
f. And e, respectively carrying out gas chromatographic detection on the reference substance solution, the sample solution and the sample adding solution under the condition of the step e, and recording a chromatogram. The specificity and sensitivity results are shown in Table 1:
。
the result table shows that in the method, the diluent does not interfere with impurity detection, the sensitivity of the reference substance solution is higher (the signal to noise ratio reaches 6709.5), and the detection requirement is met; the impurity in the sample solution is not detected; in the sample adding solution, the separation degree between the impurity and the 3-bromopropylamine hydrobromide is good, the impurity recovery rate is 108.45 percent, and the recovery rate is between 90 and 110 percent.
Example 2.
a. And taking a proper amount of 0.1mol/L sodium hydroxide solution, adding an equal volume of dichloromethane, fully and uniformly mixing, shaking, standing, and taking the lower layer solution as a blank solution.
b. Taking a proper amount of 3-bromopropylamine hydrobromide, adding 0.1mol/L sodium hydroxide solution for dissolution, and preparing a solution containing 0.01mg/ml of the product as an impurity stock solution; and (3) taking a proper amount of impurity stock solution, adding dichloromethane with the same volume, fully and uniformly mixing, shaking, standing, and taking the lower layer solution as a reference substance solution.
c. And (3) taking a proper amount of a peama Bei Teqi starting material, adding a certain volume of 0.1mol/L sodium hydroxide solution for dissolution to prepare a solution containing 10mg per 1ml, adding the same volume of dichloromethane, fully and uniformly mixing, shaking, standing, and taking an upper layer solution as a sample solution.
d. And (3) taking a proper amount of a peama Bei Teqi initial material, adding a proper amount of an impurity stock solution for dissolving, preparing a mixed solution containing 10mg/ml of the product and 0.01mg/ml of the impurity, adding dichloromethane with the same volume, fully and uniformly mixing, shaking, standing, and taking an upper layer solution as a sample adding solution.
e. The gas chromatograph parameters were set, the chromatographic column was Agilent CP-Sil 8CB for Amines (30 m×0.32mm,1.00 μm), the sample inlet temperature was 270 ℃, the carrier gas flow rate was 0.8ml/min, the temperature elevation program was 95℃at the initial temperature, maintained for 1min, at a temperature elevation rate of 10℃per minute to 300℃for 4min, the detector temperature was 280℃and the split ratio was 20:1.
f. And e, respectively carrying out gas chromatographic detection on the reference substance solution, the sample solution and the sample adding solution under the condition of the step e, and recording a chromatogram. And comparing the sample solution map with the sample adding solution map, wherein no 3-bromopropylamine hydrobromide impurity is detected in the sample solution.
Claims (4)
1. A method for detecting 3-bromopropylamine hydrobromide impurities in a starting material of pema Bei Teqi by gas chromatography, comprising the steps of:
a. taking a proper amount of 3-bromopropylamine hydrobromide, adding 0.1mol/L sodium hydroxide solution for dissolution, and preparing 0.01mg/ml 3-bromopropylamine hydrobromide solution as an impurity stock solution; adding an appropriate amount of impurity stock solution into an organic solvent with the same volume, fully and uniformly mixing, shaking, standing, and taking an upper layer solution as a reference substance solution;
b. taking a proper amount of a peama Bei Teqi starting material, adding a certain volume of 0.1mol/L sodium hydroxide solution for dissolution to prepare a 10mg/ml peama Bei Teqi starting material solution, adding an organic solvent with the same volume, fully and uniformly mixing, shaking, standing, and taking an upper layer solution as a sample solution;
c. taking a proper amount of a peama Bei Teqi starting material, adding a proper amount of an impurity stock solution for dissolution, preparing a mixed solution containing 10mg/ml of a peama Bei Teqi starting material and 0.01mg/ml of an impurity, adding an organic solvent with the same volume, fully and uniformly mixing, shaking, standing, and taking an upper layer solution as a sample adding solution;
d. setting gas chromatograph parameters, wherein the temperature of a sample inlet is 270-290 ℃, the flow rate of carrier gas is 0.8-1.2 ml/min, the temperature rising program is that the initial temperature is 95-105 ℃, the temperature is maintained for 1-3 min, the temperature rising speed is 10-20 ℃ per minute to 300 ℃, the temperature is maintained for 4-6 min, the temperature of a detector is 280-300 ℃, and the split ratio is 10:1-20:1;
e. and d, respectively carrying out gas chromatography detection on the reference substance solution, the sample solution and the sample adding solution under the condition of the step d, then obtaining a map, judging whether the impurity 3-bromopropylamine hydrobromide exists according to the sample solution map and the sample adding, and comparing the impurity 3-bromopropylamine hydrobromide with the reference substance solution map according to the sample solution map and the sample adding so as to obtain the content of the impurity 3-bromopropylamine hydrobromide.
2. A method for detecting 3-bromopropylamine hydrobromide impurity in a starting material of pema-Bei Teqi by gas chromatography as claimed in claim 1, wherein: the organic solvent in the step a, the step b and the step c is one or more of n-hexane, n-heptane, methylene dichloride or ethyl acetate.
3. A method for detecting 3-bromopropylamine hydrobromide impurity in a starting material of pemadx Bei Teqi by gas chromatography as claimed in claim 1, wherein: in the step e, the sample injection amount of the sample adding solution, the sample solution and the reference substance solution is 1-3 mu l.
4. A method for detecting 3-bromopropylamine hydrobromide impurity in a starting material of pemadx Bei Teqi by gas chromatography as claimed in claim 1, wherein: in step d, the chromatographic column was an Agilent CP-Sil 8CB for Amines (30 m×0.32mm,1.00 μm), the inlet temperature was 280 ℃, the carrier gas flow rate was 1ml/min, the temperature elevation program was 100℃at the initial temperature, maintained for 2min, the temperature elevation rate was 20℃per minute to 300℃for 5min, the detector temperature was 300℃and the split ratio was 10:1.
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| CN202310986358.5A CN116735756A (en) | 2023-08-08 | 2023-08-08 | Detection method for measuring 3-bromopropylamine hydrobromide impurity in peama Bei Teqi starting material by gas chromatography |
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| CN202310986358.5A CN116735756A (en) | 2023-08-08 | 2023-08-08 | Detection method for measuring 3-bromopropylamine hydrobromide impurity in peama Bei Teqi starting material by gas chromatography |
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