CN105326787A - Technology for preparing dexamethasone sodium phosphate injection - Google Patents
Technology for preparing dexamethasone sodium phosphate injection Download PDFInfo
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- CN105326787A CN105326787A CN201510758757.1A CN201510758757A CN105326787A CN 105326787 A CN105326787 A CN 105326787A CN 201510758757 A CN201510758757 A CN 201510758757A CN 105326787 A CN105326787 A CN 105326787A
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- dexamethasone
- sodium phosphate
- dexamethasone sodium
- phosphate
- recrystallization
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Abstract
The invention relates to a technology for preparing a dexamethasone sodium phosphate injection. The technology includes the following steps that dexamethasone sodium phosphate is prepared, wherein dexamethasone acetate epoxide serves as a staring material, a dexamethasone sodium phosphate solution is obtained sequentially through a ring-opening reaction, recrystallization achieved through acetone or diethyl ether, base-catalyzed hydrolysis, pyrophosphoryl chloride esterification and a salt formation reaction achieved through neutralization, and the dexamethasone sodium phosphate solution is recrystallized to obtain a dexamethasone sodium phosphate crystal; the dexamethasone sodium phosphate crystal is subjected to ball milling to be powder after being dried; the dexamethasone sodium phosphate powder is dissolved with injection water to be diluted, and excipient and a disodium hydrogen phosphate solution are added to prepare the dexamethasone sodium phosphate injection. By means of the technology, the problems that according to an existing preparation method, recrystallized particles are small in the recrystallization process and the content of effective components of a prepared dexamethasone sodium phosphate injection is not stable are solved.
Description
Technical field
The present invention relates to medical art, particularly, relate to the preparation technology of Decameth.
Background technology
Dexamethasone sodium phosphate, chemistry 16 Alpha-Methyl-11 β, 17 α by name, 21 trihydroxy-9 α-fuprednate-Isosorbide-5-Nitrae-diene-3,20-diketone-21-organic phosphate disodium salt, be a kind of Aeroseb-Dex, there is antiinflammatory, antiallergic, rheumatism, immunosuppressive action.The mechanism of action is: (1) antiinflammatory action: can alleviate and prevent tissue to the reaction of inflammation, thus the performance reduced inflammation.Can inflammation-inhibiting cell, comprise macrophage and leukocyte gathering at inflammation part, and suppress phagocytosis, the synthesis of lysosomal release and inflammation chemistry mediator and release.(2) immunosuppressive action: comprise prevent or T suppression cell mediation immunoreation, the anaphylaxis of retardance, reduce the number of T lymphocyte, mononuclear cell, oxyphil cell, reduce the binding ability of immunoglobulin and cell surface receptor, and suppress synthesis and the release of interleukin, thus reduce T lymphocyte to lymphocyte transformation, and alleviate and formerly send out expansion immunoreactive.Also can reduce immunity and check thing by basement membrane, and the concentration of complement component and immunoglobulin can be reduced.
Dexamethasone sodium phosphate is mainly used in anaphylaxis and auto-immune inflammatory disease, be used for connective tissue disease, activeness rheumatism, rheumatoid arthritis, lupus erythematosus, serious bronchial asthma, serious dermatitis, ulcerative colitis, acute leukemia etc., also for some severe infections and poisoning.The Comprehensive Treatment of malignant lymphoma.Within 1 hour after intramuscular injection, blood peak concentration of drug can be reached, and its plasma protein binding rate is low compared with other corticosteroids medicine, therefore clinical its injection inhibitor conventional.
Preparation method size of recrystallization particle in recrystallization process of existing dexamethasone sodium phosphate injection is less, and the active constituent content of the dexamethasone sodium phosphate injection made is unstable.
Summary of the invention
Technical problem to be solved by this invention is to provide the preparation technology of Decameth, causes to overcome existing preparation method the problem of the active constituent content instability of dexamethasone sodium phosphate injection that the size of recrystallization particle in recrystallization process is less, make.
The present invention's adopted technical scheme that solves the problem is: the preparation technology of Decameth, comprises the following steps:
1), the synthesis of dexamethasone sodium phosphate: with dexamethasone acetate epoxy material for initiation material, successively through ring-opening reaction, recrystallization, alkali catalyzed hydrolysis, pyrophosphoryl chloride esterification, be neutralized into reactant salt and obtain dexamethasone sodium phosphate solution, dexamethasone sodium phosphate solution again recrystallization obtains dexamethasone sodium phosphate crystalline solid;
Described ring-opening reaction: with dexamethasone acetate epoxy material for initiation material, add HF, DMF, reaction temperature is-10 DEG C ~ 0 DEG C, and response time 3h carries out ring-opening reaction and obtains dexamethasone acetate solution;
Described recrystallization: add acetone and Tween 80 or ether and Tween 80 in dexamethasone acetate solution, carry out recrystallization and obtain dexamethasone acetate, adopt after recrystallization to revolve and steam except desolventizing, the volume ratio of acetone and Tween 80 is 3-4:1; The volume ratio of ether and Tween 80 is 2-3:1;
Described alkali catalyzed hydrolysis: the dexamethasone acetate obtained is joined Na
2cO
3with in methanol, reaction temperature 20 DEG C ~ 30 DEG C, obtains dexamethasone after response time 10min;
Described pyrophosphoryl chloride esterification: the dexamethasone obtained and pyrophosphoryl chloride, THF are obtained by reacting dexamethasone phosphate;
Describedly be neutralized into reactant salt: the dexamethasone phosphate obtained and NaOH, methanol are reacted, reaction temperature 20 DEG C ~ 30 DEG C, the response time, 1h obtained dexamethasone sodium phosphate;
2) ball milling powdered after the dexamethasone sodium phosphate crystalline solid drying, step 1) obtained;
3), by dexamethasone sodium phosphate and excipient, sodium hydrogen phosphate, sodium dihydrogen phosphate be uniformly mixed to form compositions, the weight ratio of dexamethasone sodium phosphate, excipient, sodium hydrogen phosphate, sodium dihydrogen phosphate is 1:0 ~ 100:0.01 ~ 59:0 ~ 0.5;
4) composition dissolves, by step 3) mixed in prescription water for injection, then adds recipe quantity ethanol, adds active carbon, 50 DEG C ~ 60 DEG C insulation 30min, crosses 0.22 μm of filter membrane removing active carbon, obtains dexamethasone sodium phosphate injection.
Reagent used in the present invention is available reagent, and wherein HF is Fluohydric acid., and DMF is dimethyl formamide, and the step that the present invention prepares dexamethasone sodium phosphate is simple, and raw material is easy to get, and reaction condition is gentle, is suitable for suitability for industrialized production, and with low cost; The present invention, by adding phosphate buffered solution in dexamethasone sodium phosphate injection, effectively can avoid the problem that the effective ingredient drug effect of dexamethasone sodium phosphate injection reduces; The present invention adopts acetone to be used for the recrystallization of dexamethasone acetate, can effectively improve dexamethasone acetate recrystallization ratio, and then improves the yield of final products dexamethasone sodium phosphate; And the present invention is by adding Tween 80 in recrystallizing technology step, when making recrystallization, recrystallization particle is comparatively large, and degree of scatter is better.
Further, in step 1), the mol ratio of dexamethasone acetate epoxy material, HF, DMF is 1 ~ 2:92 ~ 95:44 ~ 50.
Further, dexamethasone acetate, Na in step 3)
2cO
3, methanol mol ratio be 1 ~ 2:4 ~ 8:214 ~ 220.
Further, in step 4), the mol ratio of dexamethasone, pyrophosphoryl chloride, THF is 1 ~ 3:5 ~ 8:19 ~ 25.
Further, in step 5), the mol ratio of dexamethasone phosphate, NaOH, methanol is 1 ~ 2:2 ~ 5:169 ~ 175.
Further, one or more in described excipient glucose, lactose, sorbitol, xylitol.
To sum up, the invention has the beneficial effects as follows:
1, the present invention prepares the step of dexamethasone sodium phosphate simply, and raw material is easy to get, and reaction condition is gentle, is suitable for suitability for industrialized production, and with low cost.
2, the present invention is by the effective ingredient stable in properties at dexamethasone sodium phosphate injection.
3, the present invention adopts acetone to be used for the recrystallization of dexamethasone acetate, can effectively improve dexamethasone acetate recrystallization ratio, and then improves the yield of final products dexamethasone sodium phosphate; And the present invention is by adding Tween 80 in recrystallizing technology step, when making recrystallization, recrystallization particle is comparatively large, and degree of scatter is better.
Detailed description of the invention
Below in conjunction with embodiment, to the detailed description further of invention do, but embodiments of the present invention are not limited thereto.
Embodiment 1:
The preparation technology of Decameth, comprises the following steps:
1), the synthesis of dexamethasone sodium phosphate: with dexamethasone acetate epoxy material for initiation material, successively through ring-opening reaction, recrystallization, alkali catalyzed hydrolysis, pyrophosphoryl chloride esterification, be neutralized into reactant salt and obtain dexamethasone sodium phosphate solution, dexamethasone sodium phosphate solution again recrystallization obtains dexamethasone sodium phosphate crystalline solid;
Ring-opening reaction: with dexamethasone acetate epoxy material for initiation material, add HF, DMF, reaction temperature is-10 DEG C, and response time 3h carries out ring-opening reaction and obtains dexamethasone acetate solution, and the mol ratio of dexamethasone acetate epoxy material, HF, DMF is 1:92:44;
Described recrystallization: add acetone and Tween 80 in dexamethasone acetate solution, carries out recrystallization and obtains dexamethasone acetate, adopts to revolve to steam except desolventizing after recrystallization, and the volume ratio of acetone and Tween 80 is 3:1;
Described alkali catalyzed hydrolysis: the dexamethasone acetate obtained is joined Na
2cO
3with in methanol, reaction temperature 20 DEG C, obtains dexamethasone after response time 10min, dexamethasone acetate, Na
2cO
3, methanol mol ratio be 1:4:214;
Described pyrophosphoryl chloride esterification: the dexamethasone obtained and pyrophosphoryl chloride, THF are obtained by reacting dexamethasone phosphate, the mol ratio of dexamethasone, pyrophosphoryl chloride, THF is 1:5:19; Describedly be neutralized into reactant salt: the dexamethasone phosphate obtained and NaOH, methanol are reacted, reaction temperature 20 DEG C, the response time, 1h obtained dexamethasone sodium phosphate, and the mol ratio of dexamethasone phosphate, NaOH, methanol is 1:2:169;
2) ball milling powdered after the dexamethasone sodium phosphate crystalline solid drying, step 1) obtained;
3), by dexamethasone sodium phosphate and glucose, sodium hydrogen phosphate, sodium dihydrogen phosphate be uniformly mixed to form compositions, the weight ratio of dexamethasone sodium phosphate, sodium hydrogen phosphate is 1::0.01;
4) composition dissolves, by step 3) mixed in prescription water for injection, then adds recipe quantity ethanol, adds active carbon, 50 DEG C ~ 60 DEG C insulation 30min, crosses 0.22 μm of filter membrane removing active carbon, obtains dexamethasone sodium phosphate injection.
Embodiment 2:
The preparation technology of Decameth, comprises the following steps:
1), the synthesis of dexamethasone sodium phosphate: with dexamethasone acetate epoxy material for initiation material, successively through ring-opening reaction, recrystallization, alkali catalyzed hydrolysis, pyrophosphoryl chloride esterification, be neutralized into reactant salt and obtain dexamethasone sodium phosphate solution, dexamethasone sodium phosphate solution again recrystallization obtains dexamethasone sodium phosphate crystalline solid;
Described ring-opening reaction: with dexamethasone acetate epoxy material for initiation material, add HF, DMF, reaction temperature is-5 DEG C, and response time 3h carries out ring-opening reaction and obtains dexamethasone acetate solution, and the mol ratio of dexamethasone acetate epoxy material, HF, DMF is 1.5:94:48;
Described recrystallization: add acetone and Tween 80 in dexamethasone acetate solution, carries out recrystallization and obtains dexamethasone acetate, adopts to revolve to steam except desolventizing after recrystallization, and the volume ratio of acetone and Tween 80 is 4:1;
Described alkali catalyzed hydrolysis: the dexamethasone acetate obtained is joined Na
2cO
3with in methanol, reaction temperature 25 DEG C, obtains dexamethasone after response time 10min, dexamethasone acetate, Na
2cO
3, methanol mol ratio be 1.5:6:216;
Described pyrophosphoryl chloride esterification: the dexamethasone obtained and pyrophosphoryl chloride, THF are obtained by reacting dexamethasone phosphate, the mol ratio of dexamethasone, pyrophosphoryl chloride, THF is 2:6:22;
Describedly be neutralized into reactant salt: the dexamethasone phosphate obtained and NaOH, methanol are reacted, reaction temperature 25 DEG C, the response time, 1h obtained dexamethasone sodium phosphate, and the mol ratio of dexamethasone phosphate, NaOH, methanol is 1.5:4:173;
2) ball milling powdered after the dexamethasone sodium phosphate crystalline solid drying, step 1) obtained;
3), by dexamethasone sodium phosphate and lactose, sodium hydrogen phosphate, sodium dihydrogen phosphate be uniformly mixed to form compositions, the weight ratio of dexamethasone sodium phosphate, excipient, sodium hydrogen phosphate, sodium dihydrogen phosphate is 1:50:25:0.25;
4) composition dissolves, by step 3) mixed in prescription water for injection, then adds recipe quantity ethanol, adds active carbon, 50 DEG C ~ 60 DEG C insulation 30min, crosses 0.22 μm of filter membrane removing active carbon, obtains dexamethasone sodium phosphate injection.
Embodiment 3:
The preparation technology of Decameth, comprises the following steps:
1), the synthesis of dexamethasone sodium phosphate: with dexamethasone acetate epoxy material for initiation material, successively through ring-opening reaction, recrystallization, alkali catalyzed hydrolysis, pyrophosphoryl chloride esterification, be neutralized into reactant salt and obtain dexamethasone sodium phosphate solution, dexamethasone sodium phosphate solution again recrystallization obtains dexamethasone sodium phosphate crystalline solid;
Described ring-opening reaction: with dexamethasone acetate epoxy material for initiation material, add HF, DMF, reaction temperature is 0 DEG C, and response time 3h carries out ring-opening reaction and obtains dexamethasone acetate solution, and the mol ratio of dexamethasone acetate epoxy material, HF, DMF is 2:95:50;
Described recrystallization: add ether and Tween 80 in dexamethasone acetate solution, carries out recrystallization and obtains dexamethasone acetate, adopts to revolve to steam except desolventizing after recrystallization, and the volume ratio of ether and Tween 80 is 2:1;
Described alkali catalyzed hydrolysis: the dexamethasone acetate obtained is joined Na
2cO
3with in methanol, reaction temperature 30 DEG C, obtains dexamethasone after response time 10min, dexamethasone acetate, Na
2cO
3, methanol mol ratio be 2:8:220;
Described pyrophosphoryl chloride esterification: the dexamethasone obtained and pyrophosphoryl chloride, THF are obtained by reacting dexamethasone phosphate, the mol ratio of dexamethasone, pyrophosphoryl chloride, THF is 3:8:25;
Describedly be neutralized into reactant salt: the dexamethasone phosphate obtained and NaOH, methanol are reacted, reaction temperature 30 DEG C, the response time, 1h obtained dexamethasone sodium phosphate, and the mol ratio of dexamethasone phosphate, NaOH, methanol is 2:5:175;
2) ball milling powdered after the dexamethasone sodium phosphate crystalline solid drying, step 1) obtained;
3), by dexamethasone sodium phosphate and sorbitol, sodium hydrogen phosphate, sodium dihydrogen phosphate be uniformly mixed to form compositions, the weight ratio of dexamethasone sodium phosphate, excipient, sodium hydrogen phosphate, sodium dihydrogen phosphate is 1:100:59:0.5;
4), 4), composition dissolves that step 3) is mixed in prescription water for injection, then add recipe quantity ethanol, add active carbon, 50 DEG C ~ 60 DEG C insulation 30min, cross 0.22 μm of filter membrane removing active carbon, obtain dexamethasone sodium phosphate injection.
Embodiment 4:
The preparation technology of Decameth, comprises the following steps:
1), the synthesis of dexamethasone sodium phosphate: with dexamethasone acetate epoxy material for initiation material, successively through ring-opening reaction, recrystallization, alkali catalyzed hydrolysis, pyrophosphoryl chloride esterification, be neutralized into reactant salt and obtain dexamethasone sodium phosphate solution, dexamethasone sodium phosphate solution again recrystallization obtains dexamethasone sodium phosphate crystalline solid;
Described ring-opening reaction: with dexamethasone acetate epoxy material for initiation material, add HF, DMF, reaction temperature is 0 DEG C, and response time 3h carries out ring-opening reaction and obtains dexamethasone acetate solution, and the mol ratio of dexamethasone acetate epoxy material, HF, DMF is 2:95:50;
Described recrystallization: add ether and Tween 80 in dexamethasone acetate solution, carries out recrystallization and obtains dexamethasone acetate, adopts to revolve to steam except desolventizing after recrystallization, and the volume ratio of ether and Tween 80 is 3:1;
Described alkali catalyzed hydrolysis: the dexamethasone acetate obtained is joined Na
2cO
3with in methanol, reaction temperature 30 DEG C, obtains dexamethasone after response time 10min, dexamethasone acetate, Na
2cO
3, methanol mol ratio be 2:8:220;
Described pyrophosphoryl chloride esterification: the dexamethasone obtained and pyrophosphoryl chloride, THF are obtained by reacting dexamethasone phosphate, the mol ratio of dexamethasone, pyrophosphoryl chloride, THF is 3:8:25;
Describedly be neutralized into reactant salt: the dexamethasone phosphate obtained and NaOH, methanol are reacted, reaction temperature 30 DEG C, the response time, 1h obtained dexamethasone sodium phosphate, and the mol ratio of dexamethasone phosphate, NaOH, methanol is 2:5:175;
2) ball milling powdered after the dexamethasone sodium phosphate crystalline solid drying, step 1) obtained;
3), by dexamethasone sodium phosphate and sorbitol, sodium hydrogen phosphate, sodium dihydrogen phosphate be uniformly mixed to form compositions, the weight ratio of dexamethasone sodium phosphate, excipient, sodium hydrogen phosphate, sodium dihydrogen phosphate is 1:100:59:0.5;
4), 4), composition dissolves that step 3) is mixed in prescription water for injection, then add recipe quantity ethanol, add active carbon, 50 DEG C ~ 60 DEG C insulation 30min, cross 0.22 μm of filter membrane removing active carbon, obtain dexamethasone sodium phosphate injection.
As mentioned above, the present invention can be realized preferably.
Claims (6)
1. the preparation technology of Decameth, is characterized in that, comprises the following steps:
1), the synthesis of dexamethasone sodium phosphate: with dexamethasone acetate epoxy material for initiation material, successively through ring-opening reaction, recrystallization, alkali catalyzed hydrolysis, pyrophosphoryl chloride esterification, be neutralized into reactant salt and obtain dexamethasone sodium phosphate solution, dexamethasone sodium phosphate solution again recrystallization obtains dexamethasone sodium phosphate crystalline solid;
Described ring-opening reaction: with dexamethasone acetate epoxy material for initiation material, add HF, DMF, reaction temperature is-10 DEG C ~ 0 DEG C, and response time 3h carries out ring-opening reaction and obtains dexamethasone acetate solution;
Described recrystallization: add acetone and Tween 80 or ether and Tween 80 in dexamethasone acetate solution, carry out recrystallization and obtain dexamethasone acetate, adopt after recrystallization to revolve and steam except desolventizing, the volume ratio of acetone and Tween 80 is 3-4:1; The volume ratio of ether and Tween 80 is 2-3:1;
Described alkali catalyzed hydrolysis: the dexamethasone acetate obtained is joined Na
2cO
3with in methanol, reaction temperature 20 DEG C ~ 30 DEG C, obtains dexamethasone after response time 10min;
Described pyrophosphoryl chloride esterification: the dexamethasone obtained and pyrophosphoryl chloride, THF are obtained by reacting dexamethasone phosphate;
Describedly be neutralized into reactant salt: the dexamethasone phosphate obtained and NaOH, methanol are reacted, reaction temperature 20 DEG C ~ 30 DEG C, the response time, 1h obtained dexamethasone sodium phosphate;
2) ball milling powdered after the dexamethasone sodium phosphate crystalline solid drying, step 1) obtained;
3), by dexamethasone sodium phosphate and excipient, sodium hydrogen phosphate, sodium dihydrogen phosphate be uniformly mixed to form compositions, the weight ratio of dexamethasone sodium phosphate, excipient, sodium hydrogen phosphate, sodium dihydrogen phosphate is 1:0 ~ 100:0.01 ~ 59:0 ~ 0.5;
4) composition dissolves, by step 3) mixed in prescription water for injection, then adds recipe quantity ethanol, adds active carbon, 50 DEG C ~ 60 DEG C insulation 30min, crosses 0.22 μm of filter membrane removing active carbon, obtains dexamethasone sodium phosphate injection.
2. the preparation technology of Decameth according to claim 1, is characterized in that, in step 1), the mol ratio of dexamethasone acetate epoxy material, HF, DMF is 1 ~ 2:92 ~ 95:44 ~ 50.
3. the preparation technology of Decameth according to claim 1, is characterized in that, dexamethasone acetate, Na in step 3)
2cO
3, methanol mol ratio be 1 ~ 2:4 ~ 8:214 ~ 220.
4. the preparation technology of Decameth according to claim 1, is characterized in that, in step 4), the mol ratio of dexamethasone, pyrophosphoryl chloride, THF is 1 ~ 3:5 ~ 8:19 ~ 25.
5. the preparation technology of Decameth according to claim 1, is characterized in that, in step 5), the mol ratio of dexamethasone phosphate, NaOH, methanol is 1 ~ 2:2 ~ 5:169 ~ 175.
6. the preparation technology of Decameth according to claim 1, is characterized in that, one or more in described excipient glucose, lactose, sorbitol, xylitol.
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| CN201510758757.1A CN105326787A (en) | 2015-11-10 | 2015-11-10 | Technology for preparing dexamethasone sodium phosphate injection |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112094311A (en) * | 2020-10-16 | 2020-12-18 | 西安国康瑞金制药有限公司 | Process for preparing dexamethasone sodium phosphate by one-step method |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112094311A (en) * | 2020-10-16 | 2020-12-18 | 西安国康瑞金制药有限公司 | Process for preparing dexamethasone sodium phosphate by one-step method |
| CN112094311B (en) * | 2020-10-16 | 2022-04-08 | 西安国康瑞金制药有限公司 | Process for preparing dexamethasone sodium phosphate by one-step method |
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Application publication date: 20160217 |