CN102125565B - Medicinal composition of 24-methylene cycloartenyl ferulate - Google Patents
Medicinal composition of 24-methylene cycloartenyl ferulate Download PDFInfo
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Abstract
The invention discloses a medicinal composition of 24-methylene cycloartenyl ferulate, which solves the problem that the 24-methylene cycloartenyl ferulate is slightly soluble in water. The medicinal composition comprises the 24-methylene cycloartenyl ferulate and polyoxyl stearate; and a stable and water-soluble oryzanol medicinal composition solution is obtained by adding the 24-methylene cycloartenyl ferulate into the fused polyoxyl stearate. The invention also discloses a preparation method of the medicinal composition solution and preparation application.
Description
Technical field
The pharmaceutical composition that the invention discloses a kind of 24-methylene γ-oryzanol, comprises 24-methylene γ-oryzanol and polyoxyl stearate, belongs to field of medicaments.
Background technology
Oryzanol is that to encircle jackfruit alcohols be a kind of natural mixture that the ferulic acid ester of main body and the ferulic acid ester of sterols form, two kinds of main compositions are cycloartenyl ferulate and 24-methylene γ-oryzanol, in the oryzanol before purification not, the content of the two is about 70% left and right, is the main active in oryzanol.Discovery studies for a long period of time, oryzanol has multiple pharmacologically active, as reduce blood fat, reduce cholesterol absorption, prevent lipid oxidation, angiocardiopathy preventing, mitigation women various health obstacles and the vegetative dystonie phenomenon after entering into the climacteric period, improve diencephalon functional disorder.
In existing technical scheme, conventionally adopt and oryzanol is added the surfactants such as vegetable oil, phospholipid as injection, liposome, oral liquid etc.As Chinese patent CN123428, CN2007100156403 etc. all disclose injection oryzanol vegetable oil solubility preparation, thereby be oryzanol to be dissolved in to the solution of having prepared oryzanol in the organic solvents such as soybean oil, ethyl oleate, but this class preparation only can, for the preservation of oryzanol, cannot directly apply to human injection.If these oily solubility preparations are dissolved in to water for injection or aqueous solution for injection, there will be obvious profit two-phase layering, oryzanol precipitation, so this class preparation is without clinical value.Chinese patent application CN200910211406 discloses a kind of microemulsion formulation of oryzanol, on traditional vegetable oil basis, adds the solubilising adjuvants such as tween, glycerol, has prepared microemulsion.Although microemulsion formulation has improved the particle diameter under oryzanol solution state, this scheme need to be used a large amount of adjuvants on the one hand, and gained drug quality is restive, easily produces impurity; It has still used macromolecular oils as isopropyl myristate, Cortex cocois radicis wet goods on the other hand, and long-time stability are not good; 200710015604 disclose a kind of injection of oryzanol, use ethyl oleate as solubilizing agent, and the injection particle diameter of gained is very large, easily produce precipitation; 99103000.1 disclose a kind of water miscible sitosterol compositions that comprises simple function surfactant and multifunctional surfactant, and because needs are used multiple molecules surfactant, its stability is not good.200410094556 disclose a kind of liposome of oryzanol, adopt phospholipid as adjuvant, still have that particle diameter is large, the poor problem of long-time stability.
Although above-mentioned disclosed technical scheme is having made some progress aspect solution oryzanol water solublity, therefore but effect is not fully up to expectations, can expect that these schemes are will be poorer for solving effect aspect the worse 24-methylene of water solublity γ-oryzanol.
Comprehensive prior art, not yet occurs that pharmaceutical composition of the present invention has been obtained obvious progress on this problem for the solubilising scheme of 24-methylene γ-oryzanol.
Summary of the invention
In inventor's early-stage Study, by effectively the component in oryzanol is carried out to separation has obtained 24-methylene γ-oryzanol, the research is open in the patent 200810113430.9 of applicant's earlier application, and this full patent texts is introduced as the application's reference in full.In the research for 24-methylene γ-oryzanol sterling, applicant finds that its dissolubility in water is lower than oryzanol raw material, 1/4 left and right that only has oryzanol dissolubility, traditional solubilising scheme all cannot solve the solubilising problem of 24-methylene γ-oryzanol.Through lot of experiments, applicant is surprised to find that 24-methylene γ-oryzanol is joined in the polyoxyl stearate under molten condition and can access completely and dissolve, adds the resulting 24-methylene of water γ-oryzanol medicinal composition solution to have excellent stability and good dissolubility in this fused solution.Based on this, find, the invention provides a kind of stable, significantly improved the deliquescent pharmaceutical composition of 24-methylene γ-oryzanol, comprise 24-methylene γ-oryzanol and polyoxyl stearate.The present invention also further provides and has contained the pharmaceutical preparation that above pharmaceutical composition and other pharmacy can be accepted adjuvant.Meanwhile, the present invention also provides the preparation method of above compositions.
The pharmaceutical composition that the invention discloses a kind of 24-methylene γ-oryzanol, comprises 24-methylene γ-oryzanol and polyoxyl stearate.In pharmaceutical composition of the present invention, the mass ratio of 24-methylene γ-oryzanol and polyoxyl stearate is 1: 5-200, is preferably 1: 10-100, most preferably is 1: 20-60.
In the present invention, the source of 24-methylene γ-oryzanol is not restricted, although applicant provides a kind of method for separating and preparing of this compound in foregoing, yet those skilled in the art still can adopt the technological means such as other chemosynthesis, separation and purification to obtain 24-methylene γ-oryzanol, and it is still applicable to solubilising scheme disclosed by the invention.As well known to those skilled in the art, by different separation methods or the resulting 24-methylene of purifying technique γ-oryzanol purity, be that tool is discrepant, as long as application technical scheme of the present invention both can obtain pharmaceutical composition of the present invention.
In the present invention, described polyoxyl stearate is a kind of pharmaceutically generally for the emulsifying agent adjuvant of injection, and at the polymer that is chemically polyethylene glycol mono stearate, molecular formula is C
17h
35cOO (CH
2cH
2o) nH, n represents the different degree of polymerization, conventionally pharmaceutically application have a n=2,6,8,10,12,20,25,30,32,40,50,60,100,150 etc., all can be applied to pharmaceutical composition of the present invention.Applicant finds by great many of experiments, use the polyoxyl stearate of n=40 for solubilising 24-methylene γ-oryzanol best results, and consumption can be effectively controlled, therefore being preferably applied to polyoxyl stearate of the present invention is s6 (being called for short s40), be n=40, its fusing point is 46-51 ℃.By 24-methylene γ-oryzanol is dissolved in the polyoxyl stearate of molten state, 24-methylene γ-oryzanol disperses completely in the Molecular Geometries of polyoxyl stearate, thereby by polyoxyl stearate institute enclose, solved the problem that 24-methylene γ-oryzanol is insoluble in water.
In the present invention, in order further to improve the stability of pharmaceutical composition, can add synergist, applicable synergist can be:
Poloxamer in Pluronic F68, preferably PLURONICS F87;
Lecithin, comprises egg yolk lecithin, soybean phospholipid, preferably soya lecithin;
Polyalcohols, comprises organic polyhydric alcohol liquid under room temperature, preferably propylene glycol, glycerol, ethylene glycol or its mixture;
Tweens, preferably polysorbate40, polysorbate60, Tween 80, most preferably Tween 80;
Basic amino acid acids, comprises one or more the mixture in lysine, arginine, histidine, preferably arginine;
Polyoxyethylene castor oil and derivant thereof (EL), especially polyoxyethylene hydrogenated Oleum Ricini (RH), preferably EL35, RH40.
Preferably, for the synergist of pharmaceutical composition of the present invention, be tween, basic amino acid, polyoxyethylene castor oil, the mixture of one or more in Tween 80, arginine, EL35 more preferably.
When pharmaceutical composition of the present invention adds above-mentioned synergist, its amount adding can be adjusted according to actual needs, preferably adopts the 1/20-1 of polyoxyl stearate quality doubly.
Test shows, pharmaceutical composition of the present invention has significantly improved the water solublity of 24-methylene γ-oryzanol, and has good stability.The test that applicant carries out simultaneously shows, add synergist not only can increase the stability of pharmaceutical composition of the present invention, and can further improve its water solublity: under equal consumption polyoxyl stearate, add synergist can dissolve more 24-methylene γ-oryzanol.
On the other hand, the present invention also provides the preparation method of described pharmaceutical composition, comprises polyoxyl stearate is heated to molten condition, adds wherein the step of 24-methylene γ-oryzanol, further comprises the steps:
1. polyoxyl stearate is heated to melting, adds wherein 24-methylene γ-oryzanol to stir it is dissolved completely.
2. the fused solution of step 1 is joined in water or aqueous solution, stir it is uniformly dissolved.
In above-mentioned preparation method step 1, for the polyoxyl stearate of different model, there is different fusing points, therefore when heating, need to adopt different heating-up temperatures, this is apparent to those skilled in the art.
In above-mentioned preparation method step 2, can in water, add pharmaceutic adjuvant, can be especially above-mentioned synergist.According to the those skilled in the art that need of final products and preparation, can select different adjuvants to add.
On the basis of foregoing invention, pharmaceutical composition of the present invention can be prepared into different preparations and enter human body by suitable route of administration, normally oral liquid or injection, freeze-dried powder.Can adopt any adaptable formulation method that pharmaceutical composition of the present invention is prepared into pharmaceutical preparation.For example can be by the medicinal composition solution 0.45um membrane filtration of above-mentioned steps 2 gained, detect qualified after, dress oral liquid bottle; The medicinal composition solution of above-mentioned steps 2 gained can be carried out to the techniques such as fine straining, dress cillin bottle through simple decarburization filtration sterilization, 0.22um microporous filter membrane and be prepared as injection; Can add the suitable suitable freeze-dry process of employing such as lyophilizing proppant to be prepared into freeze-dried powder the medicinal composition solution of above-mentioned steps 2 gained.To those skilled in the art, these preparation process are well-known.Same, according to different preparation needs, can add the common excipient substance in this area, also well known to a person skilled in the art, for example can add antioxidant, as EDTA, sodium metasulfite, sodium sulfite etc.; Fluidizer, as micropowder silica gel; Fragrance correctives, as saccharin sodium, Herba Menthae etc.
Applicant has carried out experimental results show that to the dissolubility of pharmaceutical composition of the present invention and stability pharmaceutical composition of the present invention has significantly improved the water solublity of 24-methylene γ-oryzanol, and has good stability.
The specific embodiment
Embodiment 1
Get 20g s40, at 60 ℃, be heated to molten condition, then add wherein 4g24-methylene γ-oryzanol, mix and blend 30min, gained fused solution is joined in 5L water for injection and stirred to dissolving completely, both obtained pharmaceutical composition of the present invention, concentration is 0.8mg/ml.
The clarification completely at room temperature standing 24 hours of gained solution.
Gained medicinal composition solution 0.45um membrane filtration, detect qualified after, dress oral liquid bottle, both 400 of drug composition oral preparations of the present invention.
Embodiment 2
Get 100g s32, at 60 ℃, be heated to molten condition, then add wherein 5g24-methylene γ-oryzanol, mix and blend 50min, gained fused solution is joined in 3L water for injection and stirred to dissolving completely, both obtained pharmaceutical composition of the present invention, concentration is 0.7mg/ml.
The clarification completely at room temperature standing 24 hours of gained solution.
0.3% injection activated carbon for gained medicinal composition solution is stirred 30 minutes, after decarburization is filtered, 0.22um microporous filter membrane carry out filling after fine straining cillin bottle both 500 of medicine composition injections of the present invention.
Embodiment 3
Get 200g s40, at 70 ℃, be heated to molten condition, then add wherein 4g 24-methylene γ-oryzanol, mix and blend 30min, gained fused solution is joined in 4L water for injection and stirred to dissolving completely, both obtained pharmaceutical composition of the present invention, concentration is 1mg/ml.
The clarification completely at room temperature standing 24 hours of gained solution.
Add 0.3% injection activated carbon to stir 30 minutes aforementioned pharmaceutical compositions solution, after decarburization is filtered, 0.22um microporous filter membrane carries out, after fine straining, adopting following freeze-dry process:
Pre-freeze: products temperature drops to-45 ℃, is incubated and can carries out sublimation drying after 3 hours;
Sublimation drying: sublimation drying temperature is controlled at below-12 ℃;
Dry again: drying stage maximum temperature is controlled at 35 ℃ again, and loss on drying should be up to specification;
After dry end, the intrinsic pressure plug of case, outlet lock aluminium lid, the qualified rear packing of product inspection obtains 400 of lyophilized injection of pharmaceutical composition of the present invention.
Embodiment 4
Get 400g s60, at 80 ℃, be heated to molten condition, then add wherein 4g 24-methylene γ-oryzanol, mix and blend 30min, gained fused solution is joined in 2L water for injection and stirred to dissolving completely, both obtained pharmaceutical composition of the present invention, concentration is 2mg/ml.
The clarification completely at room temperature standing 24 hours of gained solution.
Embodiment 5
Get 40g s40, at 60 ℃, be heated to molten condition, then add wherein 5g24-methylene γ-oryzanol, mix and blend 30min, gained fused solution is joined to have dissolved in the arginic 2L water for injection of 3g and stir to dissolving completely, both obtained pharmaceutical composition of the present invention, concentration is 2.5mg/ml.
The clarification completely at room temperature standing 24 hours of gained solution.
Embodiment 6
Get 120g s60, at 90 ℃, be heated to molten condition, then add wherein 10g24-methylene γ-oryzanol, mix and blend 30min, gained fused solution is joined in the 2L water for injection that has dissolved 10g Tween 80 and stir to dissolving completely, both obtained pharmaceutical composition of the present invention, concentration is 5mg/ml.
The clarification completely at room temperature standing 24 hours of gained solution.
Embodiment 7
Get 150g s150, at 90 ℃, be heated to molten condition, then add wherein 10g 24-methylene γ-oryzanol, mix and blend 30min, gained fused solution is joined in the 1L water for injection that has dissolved 30g EL35 and stir to dissolving completely, both obtained pharmaceutical composition of the present invention, concentration is 10mg/ml.
The clarification completely at room temperature standing 24 hours of gained solution.
Embodiment 8
Get 200g s40, at 60 ℃, be heated to molten condition, then add wherein 15g24-methylene γ-oryzanol, mix and blend 30min, makes its complete mix homogeneously to fused solution.Get 10g arginine and be dissolved in 1L water for injection, add fused solution completely after mixed dissolution, stir to dissolving completely, both obtained pharmaceutical composition of the present invention, concentration is 15mg/ml.
The clarification completely at room temperature standing 24 hours of gained solution.
Embodiment 9
Get 10g Tween 80 and 10g propylene glycol, join in 2L aqueous solution, stir to dissolving completely.
Get 100g s20, at 80 ℃, be heated to molten condition, then add wherein 8g24-methylene γ-oryzanol, mix and blend 20min, gained fused solution is stirred to dissolving completely in above-mentioned Tween solution, both obtained pharmaceutical composition of the present invention, concentration is 4mg/ml.
The clarification completely at room temperature standing 24 hours of gained solution.
Embodiment 10
Get 10g lysine, 10g histidine, join mixing and stirring in 2L water for injection.
Get 100g s150, at 90 ℃, be heated to molten condition, then add wherein 10g 24-methylene γ-oryzanol, mix and blend 30min, gained fused solution is joined in above-mentioned aqueous solution and stirred to dissolving completely, both obtained pharmaceutical composition of the present invention, concentration is 5mg/ml.
The clarification completely at room temperature standing 24 hours of gained solution.
Embodiment 11
Get 100g s40, at 70 ℃, be heated to molten condition, then add wherein 5g 24-methylene γ-oryzanol, mix and blend 20min, gained fused solution is joined in 2L water for injection and stirred to dissolving completely, both obtained pharmaceutical composition of the present invention, concentration is 2.5mg/ml.
The clarification completely at room temperature standing 24 hours of gained solution.
Embodiment 12
Get 50g s40, at 70 ℃, be heated to molten condition, then add wherein 12g 24-methylene γ-oryzanol, mix and blend 20min, obtains fused solution.Get 5g arginine and join and in 2L water for injection, stir to dissolving completely, then add above-mentioned fused solution to be stirred to completely and dissolve, both pharmaceutical composition of the present invention, concentration is 6mg/ml.
The clarification completely at room temperature standing 24 hours of gained solution.
Comparative example 1
PLURONICS F87 80g
Maltose cyclodextrin 240g
Colloidal silica 22g
Starch 75g
24-methylene γ-oryzanol 1120g
Water for injection 10L
PLURONICS F87 is joined in 1L water, at 60 ℃, heated and stirred is uniformly dissolved completely to it, then add wherein remaining water, and add starch, maltose cyclodextrin, colloidal silica, 24-methylene γ-oryzanol, stir and make its complete mix homogeneously both obtain injection.
Comparative example 2
2g 24-methylene γ-oryzanol is joined in 8g Oleum Cocois, take 10g Tween 80 as emulsifying agent, 10g glycerol is cosolvent, be diluted with water to 1L be stirred to complete mix homogeneously both injection.
Comparative example 3
Get 100g s40, join in 1L water and stir it is dissolved completely, then add wherein 5g24-methylene γ-oryzanol, mix and blend 30min, is settled to 2L with water for injection, has both obtained injection.
Dissolve hardly, occur obvious sediment after placing half an hour under room temperature.
Comparative example 4
Get 300g PEG4000, at 80 ℃, be heated to molten condition, then add wherein 10g24-methylene γ-oryzanol, mix and blend 30min, gained fused solution is joined in 2L water for injection and stirred to dissolving completely, and resulting composition concentration is 5mg/ml.
Gained solution is clarification substantially after at room temperature standing 24 hours.
Comparative example 5
Get 300g PVP K30, at 80 ℃, be heated to molten condition, then add wherein 10g24-methylene γ-oryzanol, mix and blend 30min, gained fused solution is joined in 2L water for injection and stirred to dissolving completely, and resulting composition concentration is 5mg/ml.
Gained solution keeps basic clarification at room temperature standing one hour, then starts to occur muddy.
Comparative example 6
Get 300g PLURONICS F87, at 80 ℃, be heated to molten condition, then add wherein 10g24-methylene γ-oryzanol, mix and blend 30min, gained fused solution is joined in 2L water for injection and stirred to dissolving completely, and resulting composition concentration is 5mg/ml.
Gained solution starts muddiness after at room temperature standing 24 hours has obvious sediment to separate out.
For above-mentioned sample, applicant has carried out stability test, specific as follows:
Get the solution of embodiment 11,12 and comparative example 1,2,4 solution (being designated as sample number 1-5) is at room temperature preserved 1 year, detect its changes of contents, and record its clarification situation, outcome record is in following table:
Table 1: long-time stability experimental result
From above-mentioned data, traditional for the scheme that solves oryzanol problem hard to tolerate for solve the worse 24-methylene of water solublity γ-oryzanol be do not have resultful, the melting that adopts other is with adjuvant for 24-methylene γ-oryzanol also poor effect, and resulting ejection preparation all cannot be realized stable preservation; Technical scheme of the present invention can provide the medicinal composition solution of the 24-methylene γ-oryzanol of clarification steady in a long-term.
Meanwhile, applicant gets the medicinal composition solution of embodiment 11,12 and comparative example 1,2,4 injection (label is 1-5 respectively) has carried out particle diameter test, and acquired results is as shown in table 2 below:
Table 2: particle diameter test result
From above-mentioned data, medicinal composition solution of the present invention belongs to the scope of micelle, more approaches true solution. and particle diameter is very large for solution prepared by employing prior art scheme, belongs to the particle size range of suspension or emulsion.Also can find out that thus traditional scheme is infeasible for solving the water-soluble problem of 24-methylene γ-oryzanol.
By table 1,2 data, found out, on the basis of technical solution of the present invention, add described synergist can significantly improve the particle diameter of medicinal composition solution of the present invention, and significantly improve its stability.
Claims (11)
1. a pharmaceutical composition, comprises 24-methylene γ-oryzanol and polyoxyl stearate, and wherein the mass ratio of 24-methylene γ-oryzanol and polyoxyl stearate is 1: 5-200, and do not comprise 1: 5.
2. according to the pharmaceutical composition of claim 1, the mass ratio of 24-methylene γ-oryzanol and polyoxyl stearate is 1: 10-100.
3. according to the pharmaceutical composition of claim 1, the mass ratio of 24-methylene γ-oryzanol and polyoxyl stearate is 1: 20-60.
4. according to the pharmaceutical composition of claim 1, described polyoxyl stearate is s6.
5. according to the pharmaceutical composition of above-mentioned arbitrary claim, also comprise synergist, described synergist is selected from following one or more mixture: poloxamer, lecithin, polyhydric alcohol, basic amino acid, polyoxyethylene castor oil and derivant thereof, tween, wherein said polyoxyethylene castor oil and derivant thereof are selected from polyoxyethylene castor oil 35 or polyoxyethylene hydrogenated Oleum Ricini 40 or the mixture of the two.
6. according to the pharmaceutical composition of claim 5, described synergist is selected from one or more the mixture in lysine, arginine, histidine.
7. according to the pharmaceutical composition of claim 5, described synergist is selected from Tween 80.
8. according to the pharmaceutical composition of claim 5, described synergist is selected from polyoxyethylene castor oil 35 or polyoxyethylene hydrogenated Oleum Ricini 40 or the mixture of the two.
9. the preparation method of pharmaceutical composition described in claim 1, comprise polyoxyl stearate is heated to molten condition, the step that adds wherein 24-methylene γ-oryzanol, wherein, the mass ratio of 24-methylene γ-oryzanol and polyoxyl stearate is 1: 5-200, and do not comprise 1: 5.
10. according to the preparation method of claim 9, comprise the steps:
(1). polyoxyl stearate is heated to melting, adds wherein 24-methylene γ-oryzanol to stir it is dissolved completely;
(2). the fused solution of step 1 is joined in water or aqueous solution, stir it is uniformly dissolved.
11. according to the preparation method of claim 10, is included in the step that adds synergist in step 2.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101590008A (en) * | 2008-05-29 | 2009-12-02 | 北京世纪博康医药科技有限公司 | A kind of composite preparation and purifying process of 24-methylene basic ring jackfruit alcohol ferulic acid ester |
| CN102058515A (en) * | 2009-11-18 | 2011-05-18 | 北京世纪博康医药科技有限公司 | Solid dispersion of 24-methylene cycloartanol ferulic acid eater and preparation thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101590008A (en) * | 2008-05-29 | 2009-12-02 | 北京世纪博康医药科技有限公司 | A kind of composite preparation and purifying process of 24-methylene basic ring jackfruit alcohol ferulic acid ester |
| CN102058515A (en) * | 2009-11-18 | 2011-05-18 | 北京世纪博康医药科技有限公司 | Solid dispersion of 24-methylene cycloartanol ferulic acid eater and preparation thereof |
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