CN101618019B - Triamcinolone acetonide acetate particle, and preparation method and medicinal composition thereof - Google Patents
Triamcinolone acetonide acetate particle, and preparation method and medicinal composition thereof Download PDFInfo
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- CN101618019B CN101618019B CN2008100399656A CN200810039965A CN101618019B CN 101618019 B CN101618019 B CN 101618019B CN 2008100399656 A CN2008100399656 A CN 2008100399656A CN 200810039965 A CN200810039965 A CN 200810039965A CN 101618019 B CN101618019 B CN 101618019B
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Abstract
The invention discloses a triamcinolone acetonide acetate particle, and a preparation method and a medicinal composition thereof. The preparation method comprises the following steps: 1) heating and dissolving triamcinolone acetonide acetate with aqueous solution of ethanol, naturally cooling the obtained solution to obtain acicular crystals, washing away the ethanol from the crystals with water for injection, drying the washed crystals, and then adding the crystals into water for injection at a temperature of 0 to 10 DEG C; 2) linearly adding dropwise triamcinolone acetonide acetate solution dissolved with dimethyl formamide solution into the mixed solution of the water for injection at the temperature of 0 to 10 DEG C obtained in the step 1), simultaneously stirring the mixed solution, keeping the temperature of the mixed solution at 0 to 15 DEG C, and continuing stirring the mixed solution for 1 to 30 minutes to obtain a mixture of water and crystals; and 3) as usual, filtering the mixture of the water and the crystals obtained in the step 2) and vacuum-drying the obtained crystals. The invention adopts a crystal inoculation process, thus crystals of the prepared triamcinolone acetonide acetate particles have regular shapes and uniform particle sizes; crystallization is free from jet milling and the physicochemical property of the particle is stable; and no crystal expansion phenomenon generates in the prepared triamcinolone acetonide acetate suspension injection during storage.
Description
Technical field
The present invention be more particularly directed to a kind of triamcinolone acetonide acetate particle and preparation method thereof and pharmaceutical composition.
Background technology
The triamcinolone acetonide acetate injection is a glucocorticoid medicine commonly used clinically.Be applicable to various dermatosiss, allergic rhinitis, arthralgia, bronchial asthma, scapulohumeral periarthritis, tenosynovitis, synovitis, acute sprain, rheumatoid arthritis etc.
The triamcinolone acetonide acetate injection is a suspensoid injectio.Triamcinolone acetonide acetate adopts the dimethyl formamide solvent crystallization to make triamcinolone acetonide acetate particle in the preparation pretreatment at present.Its technology may further comprise the steps.
1. water for injection is cooled to below 5 ℃.
2. dimethyl formamide is heated to more than 60 ℃, drops into triamcinolone acetonide acetate, stirring makes it molten entirely, filters.
3. filtrate is filtered, once be added in the water for injection that is cooled to below 5 ℃, stir.
4. mixeding liquid temperature is remained on below 15 ℃, continue to stir 30 minutes, stop immediately stirring.
5. the mixture with water and crystal filters.Crystallization is with filterable water for injection cyclic washing.
6. microcrystallization is evenly placed the dish of cleaning, vacuum drying.Dry back comminution by gas stream promptly gets triamcinolone acetonide acetate particle.Can prepare the triamcinolone acetonide acetate suspensoid injectio.
Yet there is following major defect in present technology.(1) wayward crystal habit.(2) 5% left and right sides grain size numbers are greater than 50 microns.(3) comminution by gas stream may cause part microgranule physicochemical property to change.(4) made suspensoid injectio has the brilliant phenomenon that rises in storing.
Summary of the invention
Therefore, the technical problem to be solved in the present invention is exactly the defective at the preparation method existence of existing triamcinolone acetonide acetate particle, a kind of new triamcinolone acetonide acetate particle and preparation method thereof and pharmaceutical composition are provided, compare with existing technology, this method has that controllability is strong, preparation stabilization, advantage such as easy and simple to handle.
Inventor's Dichlorodiphenyl Acetate triamcinolone acetonide microgranule technology is furtherd investigate, physicochemical property according to triamcinolone acetonide acetate particle, in triamcinolone acetonide acetate particle preparation technology, adopt microcrystallization co-crystallization inocalation method technological means first, and further particle crystallization is optimized, thereby developed the triamcinolone acetonide acetate particle preparation method that a kind of controllability is strong, preparation stability is high.
The present invention solves the problems of the technologies described above the technical scheme that is adopted: a kind of preparation method of triamcinolone acetonide acetate particle may further comprise the steps:
1) with ethanol water with the triamcinolone acetonide acetate heating for dissolving after natural cooling, acicular crystal, with drying behind the ethanol in the crystallization of water for injection flush away, then in the water for injection with 0 ℃~10 ℃ of crystallization addings;
2) with the dissolved triamcinolone acetonide acetate solution of dimethyl formamide, wire drips in 0 ℃~10 ℃ water for injection mixed liquor of step 1) gained, stirs while dripping, and keeps 0 ℃~15 ℃ of mixeding liquid temperatures, continue to stir 1~30 minute, get water and crystalline mixture;
3) according to routine, with step 2) water of gained and crystalline mixture filter, and will filter gained crystallization vacuum drying afterwards.
According to the present invention, with the triamcinolone acetonide acetate heating for dissolving, natural cooling gets acicular crystal to step 1) then with ethanol water, with drying behind the ethanol in the crystallization of water for injection flush away, then in the water for injection with 0 ℃~10 ℃ of crystallization addings.That wherein, the concentration expressed in percentage by weight of described ethanol water is preferable is 75%-95%.Ethanol in the preferable water for injection flush away crystallization of using normal temperature condition (10 ℃~30 ℃).Described oven dry is preferably 100 ℃ of oven dry.The triamcinolone acetonide acetate crystallization adds in the water for injection then, as next step crystalline nucleus, what addition was preferable is step 2) one thousandth of the triamcinolone acetonide acetate particle amount of final gained arrives one of percentage in the water for injection, and the temperature of water for injection is 0 ℃~10 ℃, preferred 0 ℃~5 ℃.
According to the present invention, step 2) with the dissolved triamcinolone acetonide acetate solution of dimethyl formamide, wire drips in 0 ℃~10 ℃ water for injection mixed liquor of step 1) gained, stir while dripping, keep 0 ℃~15 ℃ of mixeding liquid temperatures, continue to stir 1~30 minute, get water and crystalline mixture.Wherein, the dissolved triamcinolone acetonide acetate solution of described dimethyl formamide can be the conventional solution that is heated to dissolving triamcinolone acetonide acetate gained more than 60 ℃ with dimethyl formamide, this solution does not need saturated, filters the filtrate of gained then, removes the crystallization that may separate out in the solution.The filtrate wire of gained drips in 0 ℃~10 ℃ of the step 1) gained, and in preferred 0 ℃~5 ℃ water for injection mixed liquor, described wire drips preferable rate of addition and is about 100ml/min, and speed of agitator is 120 commentaries on classics/min.Wire dropping mode is more even, tiny than the prepared crystallization particle diameter of disposable adding mode.What the dripping quantity of triamcinolone acetonide acetate and the weight ratio of water for injection were preferable is 1: 35~1: 80, and better is 1: 45~1: 60.Mixeding liquid temperature keeps 0 ℃~15 ℃ when continuing to stir, and preferable is 0 ℃~10 ℃, and better is 0 ℃~5 ℃.The time of continuing to stir is 1~30 minute, preferred 5 minutes.Alr mode of the present invention and speed can be the conventional methods of this area.
According to the present invention, step 3) according to routine with step 2) water of gained and crystalline mixture filter, and will filter gained crystallization vacuum drying afterwards.Wherein, the described method of step 3) can be the ordinary skill in the art.Preferable, the crystallization after the filtration can be with the water for injection cyclic washing of filterable normal temperature condition (10 ℃~30 ℃), and flush away remains in the solvent in the crystallization.What described vacuum drying was preferable is twice seasoning, and vacuum is-the 0.06MPa condition, and first baking temperature is at 120 ℃-130 ℃, and 2 hours time, finally the baking temperature scope is 160 ℃-170 ℃, 5 hours.Promptly get triamcinolone acetonide acetate particle behind the vacuum drying, can be used for preparing the triamcinolone acetonide acetate suspensoid injectio.
The present invention also provides a kind of triamcinolone acetonide acetate particle of described preparation method preparation.
The present invention also provides a kind of pharmaceutical composition that contains triamcinolone acetonide acetate, and triamcinolone acetonide acetate wherein is above-mentioned triamcinolone acetonide acetate particle.Preferable, with conventional, also comprise pharmaceutically acceptable carrier in the described pharmaceutical composition.Described pharmaceutically acceptable carrier is meant the pharmaceutical carrier of pharmaceutical field routine, wherein, and diluent, excipient such as water etc.; Suspending agent such as cellulose derivative, gelatin or polyvinylpyrrolidone etc.; Wetting agent such as polyoxyethylene sorbitan monoleate etc.; In addition, can also in this pharmaceutical composition, add other adjuvant such as electrolyte.This active ingredient in pharmaceutical is the above-mentioned pharmaceutical composition that comprises triamcinolone acetonide acetate particle of the present invention of treatment effective dose.This pharmaceutical composition can adopt the method for medical domain routine, and described active component and pharmaceutically acceptable carrier are made various dosage forms, and preferable is suspensoid injectio, can be folk prescription or compound recipe.In various preparations, the content of active component is with conventional.
Can test by the various technical specifications of this area routine by the prepared triamcinolone acetonide acetate particle of the present invention, the result is as follows:
[character] this product is the crystalline powder of white or off-white color; Odorless.
This product is dissolved in chloroform, and is molten in the acetone part omitted, and slightly soluble in ethanol is insoluble in water.
Specific optical rotation is got this product, and precision claims fixed, adds the also quantitative dilution of dioxane dissolving and makes the solution that contains 10mg among every 1ml approximately, measures (Chinese Pharmacopoeia version appendix in 2005 VI E) in accordance with the law, and specific optical rotation is+92 ° to+98 °.
Granularity 90% above microgranule contains 15~20 microns and is no more than 10% less than 15 microns, individually at 20~50 microns.
Crystal formation needle-like or granular.
The about 10mg of this product is got in [discriminating] (1), adds methanol 1ml, after the tepor dissolving, adds alkaline cupric tartrate test solution 2ml, and mixing is put in the water-bath and heated, and promptly generates brick-red precipitation.
(2) get the about 20mg of this product, put in the small test tube, add 3~4 of phosphoric acid, mixing, the test tube upper end is coated with the filter paper of 5% lanthanum nitrate hexahydrate moistening, and little fire slowly is heated to and boils, after taking off the filter paper bar and adding 1 of 0.02mol/L iodine solution, add 1 of ammonia solution again, filter paper fades to bluish violet.
(3) this product shows the identification (Chinese Pharmacopoeia version appendix in 2005 III) of organic fluoride
[inspection] fluorine is got this product, measures according to fluorine inspection technique (Chinese Pharmacopoeia version appendix in 2005 VIII E), and fluorinated volume should be 3.6%~4.4%.
Related substance is got this product, adds chloroform-methanol (9: 1) and makes the solution that contains 3mg among every 1ml approximately, as need testing solution; Precision is measured 1ml, puts in the 50ml measuring bottle, adds chloroform-methanol (9: 1) and is diluted to scale, shakes up, in contrast solution.According to thin layer chromatography (appendix V B) test, draw each 10 μ l of above-mentioned two kinds of solution, put respectively on same silica gel g thin-layer plate, with benzene-dehydrated alcohol (9: 1) is developing solvent, launches, and dries, 105 ℃ of dryings 10 minutes, put coldly, spray is inspected immediately with the blue test solution of alkaline tetrazole, need testing solution is as showing the impurity speckle, must not be more than 3, the principal spot of its color and contrast solution relatively must not be darker.
Loss on drying is got this product, is dried to constant weight at 105 ℃, subtracts weight loss and must not cross 1.0% (Chinese Pharmacopoeia version appendix in 2005 VIII L).
Residue on ignition must not be crossed 0.1% (Chinese Pharmacopoeia version appendix in 2005 VIII N).
Selenium is got this product 0.10g, checks (Chinese Pharmacopoeia version appendix in 2005 VIII D) in accordance with the law, should (0.005%) up to specification.
[assay] measured according to triamcinolone acetonide acetate raw material method (Chinese Pharmacopoeia 2005 version two ones 844 pages).Press dry product and calculate, contain triamcinolone acetonide acetate C
26H
33FO
7Should be 97.0%~102.0%.
The various detections that the prepared triamcinolone acetonide acetate particle of the present invention carries out are indicated, its product quality meets the requirement of various technical specifications fully, and the triamcinolone acetonide acetate suspensoid injectio crystal habit, the particle diameter that make meet the preparation requirement, do not have the brilliant phenomenon that rises in the storage.
Raw material that the present invention is used or reagent except that specifying, all commercially available getting.
Than prior art, beneficial effect of the present invention is as follows:
(1) employing crystallization inocalation method can effectively be controlled the crystal habit in the microcrystallization process.Make crystal habit be controlled at needle-like or granular, avoided the crystal habit of hexangle type or long column type.
(2) dropping of the wire in microcrystallization process mode is more even than the prepared crystallization particle diameter of disposable adding mode.Wire drips mode 100% crystallization particle diameter below 10 microns, and disposable adding mode 5% crystallization particle diameter is greater than 50 microns.
(3) do not need comminution by gas stream, reduced in the comminution by gas stream local heating due to the airflow strikes and the microgranule physicochemical property that produces changes.
(4) prepared triamcinolone acetonide acetate suspensoid injectio does not have the brilliant phenomenon that rises in storage.
(5) be suitable for standardized production.
The specific embodiment
Further specify the present invention with embodiment below, but the present invention is not limited.The experimental technique of unreceipted actual conditions in the following example, usually according to normal condition, or the condition of advising according to manufacturer." room temperature " that the present invention narrates is meant the laboratory room temperature of this area routine, is 10 ℃~30 ℃.
Embodiment 1
1, use 20ml 75% ethanol with 0.1g triamcinolone acetonide acetate heating for dissolving, natural cooling gets acicular crystal.With the ethanol in the water for injection flush away crystallization of normal temperature condition, 100 ℃ of oven dry.
2, the triamcinolone acetonide acetate crystallization after the above-mentioned Ethanol Treatment is added in the 3500ml water for injection that is cooled to 10 ℃.
3, the 500ml dimethyl formamide is heated to 60 ℃, drops into the 100g triamcinolone acetonide acetate, stirring makes it molten entirely, filters.Filtrate wire (100ml/min) drips in above-mentioned and is cooled in 10 ℃ the water for injection, and the limit edged stirs, and rotating speed is 120 commentaries on classics/min.
4, make mixeding liquid temperature remain on 15 ℃ after adding, continue to stir 15 minutes, stop immediately stirring.The mixture of water and crystal is filtered.Crystallization is with the water for injection cyclic washing of filterable normal temperature condition.
5, microcrystallization is under vacuum-0.06MPa condition, and through 120 ℃, 2 hours, again through 160 ℃, 5 hours must triamcinolone acetonide acetate particle.
The every index of the triamcinolone acetonide acetate particle that makes all meets the requirements:
Character | Specific optical rotation | Crystal formation | Granularity | Differentiate | Check | Content |
White crystals | +93.6° | Needle-like and granular | Meet | Meet | Meet | 97.8% |
With the made triamcinolone acetonide acetate suspensoid injectio of above-mentioned microgranule conformance with standard (Chinese Pharmacopoeia 2005 version two ones 845 pages).
Embodiment 2
1, use 50ml 85% ethanol with 0.5g triamcinolone acetonide acetate heating for dissolving, natural cooling gets acicular crystal.With the ethanol in the water for injection flush away crystallization of normal temperature condition, 100 ℃ of oven dry.
2, the triamcinolone acetonide acetate crystallization after the above-mentioned Ethanol Treatment is added in the 6000ml water for injection that is cooled to 5 ℃.
3, the 500ml dimethyl formamide is heated to more than 60 ℃, drops into the 100g triamcinolone acetonide acetate, stirring makes it molten entirely, filters.Filtrate wire (100ml/min) drips in above-mentioned and is cooled in 5 ℃ the water for injection, and the limit edged stirs, and rotating speed is 120 commentaries on classics/min.
4, mixeding liquid temperature is remained on below 10 ℃ after adding, continue to stir 5 minutes, stop immediately stirring.The mixture of water and crystal is filtered.Crystallization is with the water for injection cyclic washing of filterable normal temperature condition.。
5, microcrystallization is under vacuum-0.06MPa condition, and through 125 ℃, 2 hours, again through 165 ℃, 5 hours must triamcinolone acetonide acetate particle.
The every index of the triamcinolone acetonide acetate particle that makes all meets the requirements:
Character | Specific optical rotation | Crystal formation | Granularity | Differentiate | Check | Content |
White crystals | +96.2° | Needle-like | Meet | Meet | Meet | 99.2% |
With the made triamcinolone acetonide acetate suspensoid injectio of above-mentioned microgranule conformance with standard (Chinese Pharmacopoeia 2005 version two ones 845 pages).
Embodiment 3
1, use 100ml 95% ethanol with 1g triamcinolone acetonide acetate heating for dissolving, natural cooling gets acicular crystal.With the ethanol in the water for injection flush away crystallization of normal temperature condition, 100 ℃ of oven dry.
2, the triamcinolone acetonide acetate crystallization after the above-mentioned Ethanol Treatment is added in the 8000ml water for injection that is cooled to 0 ℃.
3, the 500ml dimethyl formamide is heated to more than 60 ℃, drops into the 100g triamcinolone acetonide acetate, stirring makes it molten entirely, filters.Filtrate wire (100ml/min) drips in above-mentioned and is cooled in 0 ℃ the water for injection, and the limit edged stirs, and rotating speed is 120 commentaries on classics/min.
4, mixeding liquid temperature is remained on below 10 ℃ after adding, continue to stir 1 minute, stop immediately stirring.The mixture of water and crystal is filtered.Crystallization is with the water for injection cyclic washing of filterable normal temperature condition.
5, microcrystallization is under vacuum-0.06MPa condition, through 130 ℃ 2 hours, again through 170 ℃ 5 hours triamcinolone acetonide acetate particle.
The every index of the triamcinolone acetonide acetate particle that makes all meets the requirements:
Character | Specific optical rotation | Crystal formation | Granularity | Differentiate | Check | Content |
White crystals | +96.8° | Needle-like | Meet | Meet | Meet | 98.8% |
With the made triamcinolone acetonide acetate suspensoid injectio of above-mentioned microgranule conformance with standard (Chinese Pharmacopoeia 2005 version two ones 845 pages).
Claims (12)
1. the preparation method of a triamcinolone acetonide acetate particle may further comprise the steps:
1) with ethanol water with the triamcinolone acetonide acetate heating for dissolving after natural cooling, acicular crystal, with drying behind the ethanol in the crystallization of water for injection flush away, then in the water for injection with 0 ℃~10 ℃ of crystallization addings;
2) with the dissolved triamcinolone acetonide acetate solution of dimethyl formamide, wire drips in 0 ℃~10 ℃ water for injection mixed liquor of step 1) gained, stirs while dripping, and keeps 0 ℃~15 ℃ of mixeding liquid temperatures, continue to stir 1~30 minute, get water and crystalline mixture;
3) according to routine, with step 2) water of gained and crystalline mixture filter, and will filter gained crystallization vacuum drying afterwards.
2. preparation method according to claim 1 is characterized in that, the weight percent concentration of the described ethanol water of step 1) is 75%-95%.
3. preparation method according to claim 1 is characterized in that, the crystalline addition of the described triamcinolone acetonide acetate of step 1) is a step 2) one thousandth of the triamcinolone acetonide acetate particle amount of final gained arrives one of percentage in the water for injection.
4. preparation method according to claim 1 is characterized in that, the temperature of the described water for injection of step 1) is 0 ℃~5 ℃.
5. preparation method according to claim 1 is characterized in that step 2) rate of addition that drips of the dissolved triamcinolone acetonide acetate solution wire of described dimethyl formamide is 100ml/min, speed of agitator is 120 commentaries on classics/min.
6. preparation method according to claim 1 is characterized in that step 2) dripping quantity of described triamcinolone acetonide acetate and the weight ratio of water for injection be 1: 35~1: 80.
7. preparation method according to claim 1 is characterized in that step 2) mixeding liquid temperature remained 0 ℃~10 ℃ when described continuation was stirred, and the time of continuing to stir is 5 minutes.
8. preparation method according to claim 1 is characterized in that, the described vacuum drying of step 3) is twice seasoning, vacuum is-the 0.06MPa condition, and first baking temperature is at 120 ℃-130 ℃, 2 hours time, 160 ℃-170 ℃ of final baking temperature scopes, 5 hours.
9. the triamcinolone acetonide acetate particle of a preparation method according to claim 1 preparation.
10. a pharmaceutical composition that contains triamcinolone acetonide acetate is characterized in that, triamcinolone acetonide acetate wherein is the described triamcinolone acetonide acetate particle of claim 9.
11. pharmaceutical composition according to claim 10 is characterized in that, also comprises pharmaceutically acceptable carrier.
12. pharmaceutical composition according to claim 10 is characterized in that, this pharmaceutical composition is the triamcinolone acetonide acetate suspensoid injectio of folk prescription or compound recipe.
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Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
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CN1354652A (en) * | 1998-12-01 | 2002-06-19 | 艾文蒂斯药品有限公司 | Milling process for production of finely milled medicinal substances |
WO2004054545A1 (en) * | 2002-12-18 | 2004-07-01 | Chiesi Farmaceutici S.P.A. | Preparation of sterile aqueous suspensions comprising micronised crystalline active ingredients for inhalation |
CN1731984A (en) * | 2003-01-15 | 2006-02-08 | 陶氏环球技术公司 | Drug particles obtained by freezing onto a cold surface |
EP1782797A1 (en) * | 2005-11-02 | 2007-05-09 | Pharmatex Italia Srl | Process for the preparation of sterile powdered pharmaceutical compounds. |
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Publication number | Priority date | Publication date | Assignee | Title |
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CN1354652A (en) * | 1998-12-01 | 2002-06-19 | 艾文蒂斯药品有限公司 | Milling process for production of finely milled medicinal substances |
WO2004054545A1 (en) * | 2002-12-18 | 2004-07-01 | Chiesi Farmaceutici S.P.A. | Preparation of sterile aqueous suspensions comprising micronised crystalline active ingredients for inhalation |
CN1731984A (en) * | 2003-01-15 | 2006-02-08 | 陶氏环球技术公司 | Drug particles obtained by freezing onto a cold surface |
EP1782797A1 (en) * | 2005-11-02 | 2007-05-09 | Pharmatex Italia Srl | Process for the preparation of sterile powdered pharmaceutical compounds. |
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Address after: 200040 No. 67, Lane 5, Yuyuan Road, Shanghai, Jingan District Patentee after: Shanghai Zhengda General Pharmaceutical Co.,Ltd. Address before: 200040 No. 67, Lane 5, Yuyuan Road, Shanghai, Jingan District Patentee before: SHANGHAI GENERAL PHARMACEUTICAL Co.,Ltd. |