CN112142627A - Preparation method of tamsulosin hydrochloride crystal form - Google Patents
Preparation method of tamsulosin hydrochloride crystal form Download PDFInfo
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- CN112142627A CN112142627A CN201911401068.XA CN201911401068A CN112142627A CN 112142627 A CN112142627 A CN 112142627A CN 201911401068 A CN201911401068 A CN 201911401068A CN 112142627 A CN112142627 A CN 112142627A
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- ZZIZZTHXZRDOFM-UHFFFAOYSA-N 2-(2-ethoxyphenoxy)ethyl-[1-(4-methoxy-3-sulfamoylphenyl)propan-2-yl]azanium;chloride Chemical compound Cl.CCOC1=CC=CC=C1OCCNC(C)CC1=CC=C(OC)C(S(N)(=O)=O)=C1 ZZIZZTHXZRDOFM-UHFFFAOYSA-N 0.000 title claims abstract description 44
- 229960003198 tamsulosin hydrochloride Drugs 0.000 title claims abstract description 43
- 239000013078 crystal Substances 0.000 title claims abstract description 35
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 39
- 238000003756 stirring Methods 0.000 claims abstract description 19
- DRHKJLXJIQTDTD-OAHLLOKOSA-N Tamsulosine Chemical compound CCOC1=CC=CC=C1OCCN[C@H](C)CC1=CC=C(OC)C(S(N)(=O)=O)=C1 DRHKJLXJIQTDTD-OAHLLOKOSA-N 0.000 claims abstract description 16
- 229960002613 tamsulosin Drugs 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 14
- 239000002904 solvent Substances 0.000 claims abstract description 13
- 238000010438 heat treatment Methods 0.000 claims abstract description 11
- 239000002253 acid Substances 0.000 claims abstract description 10
- 238000001816 cooling Methods 0.000 claims abstract description 10
- 238000001035 drying Methods 0.000 claims abstract description 10
- 238000001914 filtration Methods 0.000 claims abstract description 10
- 238000004321 preservation Methods 0.000 claims abstract description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- 238000011534 incubation Methods 0.000 claims description 2
- 239000003814 drug Substances 0.000 abstract description 9
- 229940079593 drug Drugs 0.000 abstract description 7
- 238000009776 industrial production Methods 0.000 abstract description 4
- 239000007787 solid Substances 0.000 description 10
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- 238000012360 testing method Methods 0.000 description 6
- 238000002441 X-ray diffraction Methods 0.000 description 5
- 239000012295 chemical reaction liquid Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 2
- 206010067484 Adverse reaction Diseases 0.000 description 1
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 description 1
- 208000004403 Prostatic Hyperplasia Diseases 0.000 description 1
- -1 [2- (2-ethoxyphenoxy) ethyl]Amino Chemical group 0.000 description 1
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 1
- 239000000951 adrenergic alpha-1 receptor antagonist Substances 0.000 description 1
- 230000006838 adverse reaction Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- RDYMFSUJUZBWLH-UHFFFAOYSA-N endosulfan Chemical compound C12COS(=O)OCC2C2(Cl)C(Cl)=C(Cl)C1(Cl)C2(Cl)Cl RDYMFSUJUZBWLH-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Abstract
The invention belongs to the technical field of medicines, and particularly relates to a preparation method of a tamsulosin hydrochloride crystal form, which comprises the following steps: adding tamsulosin into a solvent, heating to a first temperature, and obtaining a first solution after the tamsulosin is completely dissolved; adding acid into the first solution, and carrying out heat preservation reaction at a first temperature to obtain a second solution; cooling the second solution to a second temperature, and stirring for reaction to obtain a third solution; and filtering and drying the third solution to obtain the tamsulosin hydrochloride crystal form. The preparation method has the advantages of simple process, high yield and high product purity, and is suitable for large-scale industrial production.
Description
Technical Field
The invention belongs to the technical field of medicines, and particularly relates to a preparation method of a tamsulosin hydrochloride crystal form.
Background
The chemical name of Tamsulosin Hydrochloride (Tamsulosin Hydrochloride) is 5- [ (2R) -2- [ [2- (2-ethoxyphenoxy) ethyl]Amino group]Propyl radical]-2-methoxybenzenesulphonamide hydrochloride; the molecular formula of tamsulosin hydrochloride is C20H28N2O5S & HCl with molecular weight of 444.97; tamsulosin hydrochloride has 1 chiral carbon atom in the molecular structure, and clinically used medicines are in the R configuration.
Tamsulosin hydrochloride is a novel long-acting alpha-1 adrenoceptor antagonist, was developed pharmaceutically in japan and approved by the FDA in month 7 of 1992 for marketing under the trade name of harmal (hale). The medicine can specifically inhibit the contraction of prostate smooth muscle, quickly relieve the clinical symptoms of benign prostatic hyperplasia, and has the advantages of good curative effect and few adverse reactions.
The research on the crystal forms of the drugs has great significance in the pharmaceutical industry, different crystal form solid states are formed by different molecular arrangement forms and symmetry rules of solid compounds, different crystal forms of different drugs often have different biochemical properties, and the different crystal forms have obvious differences in the aspects of stability, solubility and the like. Different crystal forms may have different solubilities, and the dissolution rate and stability of the crystal forms may be affected after the crystal forms are prepared into a certain dosage form, so that the clinical curative effect and the quality of the medicine are affected. Therefore, the research on the crystal form of the drug has an extremely important role in ensuring the stability of the drug in production and storage and the safety and effectiveness in the clinical use process.
Disclosure of Invention
The invention provides a preparation method of tamsulosin hydrochloride crystal form, which has simple process, high yield and high product purity and is suitable for large-scale industrial production.
In order to achieve the purpose, the invention adopts the following technical scheme:
the invention provides a preparation method of a tamsulosin hydrochloride crystal form, which comprises the following steps:
adding tamsulosin into a solvent, heating to a first temperature, and obtaining a first solution after the tamsulosin is completely dissolved;
adding acid into the first solution, and carrying out heat preservation reaction at a first temperature to obtain a second solution;
cooling the second solution to a second temperature, and stirring for reaction to obtain a third solution;
and filtering and drying the third solution to obtain the tamsulosin hydrochloride crystal form.
In one embodiment, the crystalline form of tamsulosin hydrochloride is form a.
In one embodiment, the first temperature is 30-85 ℃.
In one embodiment, the first temperature is 60 to 70 ℃.
In one embodiment, the solvent comprises at least one of acetonitrile, ethanol, acetone, and tetrahydrofuran.
In one embodiment, the acid comprises at least one of concentrated hydrochloric acid, acetic acid, and citric acid.
In one embodiment, the incubation time is from 1 to 20 hours.
In one embodiment, the second temperature is 20-30 ℃.
In one embodiment, the stirring reaction time is 1-20 h.
In one embodiment, the stirring speed of the stirring reaction is 100-400 rpm.
The invention provides a preparation method of a tamsulosin hydrochloride crystal form, which comprises the following steps: adding tamsulosin into a solvent, heating to a first temperature, and obtaining a first solution after the tamsulosin is completely dissolved; adding acid into the first solution, and carrying out heat preservation reaction at a first temperature to obtain a second solution; cooling the second solution to a second temperature, and stirring for reaction to obtain a third solution; and filtering and drying the third solution to obtain the tamsulosin hydrochloride crystal form. The preparation method has the advantages of simple process, high yield and high product purity, and is suitable for large-scale industrial production.
Drawings
Fig. 1 is an XRD pattern of tamsulosin hydrochloride form in example 1 of the present invention;
fig. 2 is a DSC diagram of tamsulosin hydrochloride crystal form in example 1 of the present invention.
Detailed Description
In order to make the technical problems, technical solutions and advantageous effects to be solved by the present invention more clearly apparent, the present invention is further described in detail below with reference to the following embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
The embodiment of the invention provides a preparation method of a tamsulosin hydrochloride crystal form, which comprises the following steps:
step S11, adding tamsulosin into the solvent, heating to a first temperature, and obtaining a first solution after complete dissolution;
step S12, adding acid into the first solution, and obtaining a second solution after heat preservation reaction at a first temperature;
step S13, cooling the second solution to a second temperature, and stirring for reaction to obtain a third solution;
and step S14, filtering and drying the third solution to obtain the tamsulosin hydrochloride crystal form.
Further, in step S11, the solvent includes at least one of acetonitrile, ethanol, acetone and tetrahydrofuran, and preferably the solvent is acetonitrile.
The first temperature is 30 to 85 ℃, for example, 30 ℃, 31 ℃, 32 ℃, 33 ℃, 34 ℃, 35 ℃, 40 ℃, 45 ℃, 50 ℃, 60 ℃, 70 ℃, 80 ℃, 85 ℃ and the like, preferably 60 to 70 ℃, and the temperature range is selected depending on the solvent, and when the temperature is too low, tamsulosin cannot be completely dissolved in the solvent, the raw material may not be completely reacted, and when the temperature is too high, the temperature is higher than the boiling point of the solvent.
Further, in step S12, the acid includes at least one of concentrated hydrochloric acid, acetic acid, and citric acid, and preferably the acid is hydrochloric acid.
The reaction time for the heat preservation is 1 to 20 hours, for example, 1 hour, 2 hours, 3 hours, 4 hours, 5 hours, 10 hours, 15 hours, 20 hours and the like, preferably 1 to 2 hours.
Further, in step S13, the second temperature is 20 to 30 ℃, for example, 20 ℃, 21 ℃, 22 ℃, 23 ℃, 24 ℃, 25 ℃, 30 ℃ or the like, and when the temperature is too low, the impurities are high, and when the temperature is too high, the yield is lowered.
The stirring reaction time is 1-20h, for example, 1h, 2h, 3h, 4h, 5h, 10h, 15h, 20h and the like, preferably 4-5 h, and when the temperature is too low, the yield is low.
The stirring speed of the stirring reaction is 100-400 rpm, and can be, for example, 100 rpm, 110 rpm, 120 rpm, 130 rpm, 140 rpm, 150 rpm, 200 rpm, 250 rpm, 300 rpm, 350 rpm, 400 rpm, and the like.
Further, in step S14, the tamsulosin hydrochloride crystalline form is crystalline form a.
The invention provides a preparation method of a tamsulosin hydrochloride crystal form, which comprises the following steps: adding tamsulosin into a solvent, heating to a first temperature, and obtaining a first solution after the tamsulosin is completely dissolved; adding acid into the first solution, and carrying out heat preservation reaction at a first temperature to obtain a second solution; cooling the second solution to a second temperature, and stirring for reaction to obtain a third solution; and filtering and drying the third solution to obtain the tamsulosin hydrochloride crystal form. The preparation method has the advantages of simple process, high yield and high product purity, and is suitable for large-scale industrial production.
The invention is described in further detail with reference to a number of tests performed in sequence, and a part of the test results are used as reference, and the following detailed description is given with reference to specific examples.
Example 1
Step S1: adding 5g of tamsulosin into a reaction bottle, then adding 50mL of acetonitrile, heating to 60-70 ℃, and completely dissolving to obtain a first reaction solution;
step S2: dropwise adding 7.5g of concentrated hydrochloric acid into the first reaction solution, and reacting for 1 hour at the temperature of 60-70 ℃ to obtain a second reaction solution;
step S3: slowly cooling the second reaction solution to about 25 ℃, and then stirring for 5 hours to obtain a third reaction solution;
step S4: and filtering and drying the third reaction liquid to obtain 5.17g of white solid, wherein the white solid is tamsulosin hydrochloride crystal form, HPLC (high performance liquid chromatography) is 99.98%, and the yield is 95%.
The XRD pattern of tamsulosin hydrochloride crystal form is shown in figure 1, and the testing instrument is a D2 Phaser X-ray powder diffractometer. The test conditions are as follows: an anode target, a Cu target; the pipe pressure is 30kV, and the pipe flow is 10 mA; the 2 theta scanning range is 4-50 degrees; the scanning speed is 0.6 s/step; the step size was 0.02 °/step.
The DSC chart of the tamsulosin hydrochloride crystal form is shown in figure 2, and the testing instrument is a DSC Q2000 differential scanning calorimeter. The test conditions are as follows: the heating rate is 10 ℃/min; the temperature scanning range is 40-250 ℃.
Example 2
Step S1: adding 5g of tamsulosin into a reaction bottle, adding 50mL of ethanol, heating to 70-75 ℃, and completely dissolving to obtain a first reaction solution;
step S2: dropwise adding 7.5g of concentrated hydrochloric acid into the first reaction solution, and reacting for 1 hour at the temperature of 70-75 ℃ to obtain a second reaction solution;
step S3: slowly cooling the second reaction solution to about 25 ℃, and then stirring for 5 hours to obtain a third reaction solution;
step S4: and filtering and drying the third reaction liquid to obtain 4.95g of white solid, wherein the white solid is tamsulosin hydrochloride crystal form, HPLC (high performance liquid chromatography) is 99.89%, and the yield is 91%.
The XRD pattern and DSC pattern of tamsulosin hydrochloride crystal form can be referred to example 1.
Example 3
Step S1: adding 5g of tamsulosin into a reaction bottle, adding 75mL of acetone, heating to 50-55 ℃, and completely dissolving to obtain a first reaction solution;
step S2: dropwise adding 7.5g of concentrated hydrochloric acid into the first reaction solution, and reacting for 1 hour under the condition of heat preservation to obtain a second reaction solution;
step S3: slowly cooling the second reaction solution to about 25 ℃, and stirring for 5 hours to obtain a third reaction solution;
step S4: and filtering and drying the third reaction liquid to obtain 5.28g of white solid, wherein the white solid is tamsulosin hydrochloride crystal form, HPLC (high performance liquid chromatography) is 99.80%, and the yield is 97%.
The XRD pattern and DSC pattern of tamsulosin hydrochloride crystal form can be referred to example 1.
Example 4
Step S1: adding 100g of tamsulosin into a reaction bottle, then adding 1L of acetonitrile, and heating to 60-70 ℃ to obtain a first reaction solution;
step S2: dropwise adding 150g of concentrated hydrochloric acid into the first reaction solution, and reacting for 1 hour under the condition of heat preservation to obtain a second reaction solution;
step S3: slowly cooling the second reaction solution to about 25 ℃, and stirring for 5 hours to obtain a third reaction solution;
step S4: and filtering and drying the third reaction liquid to obtain 104.6g of white solid, wherein the white solid is tamsulosin hydrochloride crystal form, HPLC (high performance liquid chromatography) is 99.96%, and the yield is 96%.
The XRD pattern and DSC pattern of tamsulosin hydrochloride crystal form can be referred to example 1.
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, equivalents and improvements made within the spirit and principle of the present invention are intended to be included within the scope of the present invention.
Claims (10)
1. A preparation method of tamsulosin hydrochloride crystal form is characterized by comprising the following steps:
adding tamsulosin into a solvent, heating to a first temperature, and obtaining a first solution after the tamsulosin is completely dissolved;
adding acid into the first solution, and carrying out heat preservation reaction at a first temperature to obtain a second solution;
cooling the second solution to a second temperature, and stirring for reaction to obtain a third solution;
and filtering and drying the third solution to obtain the tamsulosin hydrochloride crystal form.
2. The process for the preparation of crystalline form of tamsulosin hydrochloride according to claim 1, wherein said crystalline form of tamsulosin hydrochloride is form a.
3. The method for preparing tamsulosin hydrochloride crystalline form according to claim 1, wherein said first temperature is 30-85 ℃.
4. The method for preparing tamsulosin hydrochloride crystalline form according to claim 3, wherein said first temperature is 60-70 ℃.
5. The method for preparing crystalline form of tamsulosin hydrochloride of claim 1, wherein said solvent comprises at least one of acetonitrile, ethanol, acetone and tetrahydrofuran.
6. The method for preparing a crystalline form of tamsulosin hydrochloride of claim 1, wherein said acid comprises at least one of concentrated hydrochloric acid, acetic acid and citric acid.
7. The process for the preparation of crystalline form of tamsulosin hydrochloride according to claim 1, wherein the incubation reaction time is 1-20 h.
8. The method for preparing a crystalline form of tamsulosin hydrochloride according to claim 1, wherein said second temperature is 20-30 ℃.
9. The process for the preparation of crystalline form of tamsulosin hydrochloride according to claim 1, wherein the stirring reaction time is 1-20 h.
10. The method for preparing tamsulosin hydrochloride crystal form according to claim 1, wherein the stirring speed of the stirring reaction is 100-.
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| CN201911401068.XA CN112142627A (en) | 2019-12-31 | 2019-12-31 | Preparation method of tamsulosin hydrochloride crystal form |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112830888A (en) * | 2021-01-08 | 2021-05-25 | 南昌大学第一附属医院 | Preparation method of tamsulosin hydrochloride crystal form |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112830888A (en) * | 2021-01-08 | 2021-05-25 | 南昌大学第一附属医院 | Preparation method of tamsulosin hydrochloride crystal form |
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