CN103204774B - Ibuprofen compound and pharmaceutical composition thereof - Google Patents
Ibuprofen compound and pharmaceutical composition thereof Download PDFInfo
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Abstract
The invention belongs to the technical field of medicines, and particularly relates to an ibuprofen compound. The structure formula of the ibuprofen compound is shown in the specification. An X-ray powder diffraction spectrum of the Ibuprofen compound measured by a Cu-K alpha ray is shown in figure 1. A preparation method of the ibuprofen compound and a pharmaceutical composition containing the ibuprofen compound are also provided by the invention. The ibuprofen pharmaceutical composition is ibuprofen injection and Ibuprofen sterile powder injection. Compared with the prior art, the ibuprofen compound and the pharmaceutical composition thereof provided by the invention have better storage stability; and the medication safety of a sufferer is greatly improved.
Description
Technical field
The invention belongs to medical technical field, be specifically related to the preparation method of a kind of Ibuprofen BP/EP compound, this Ibuprofen BP/EP compound and the pharmaceutical composition that contains this Ibuprofen BP/EP compound.
Background technology
Ibuprofen BP/EP, English name Ibuprofen, has another name called Ibuprofen, is Non-steroidanalgetic drug.Its anti-inflammatory, analgesia, refrigeration function are respond well, and untoward reaction is less.Widespread use in the world, becomes one of global best-selling nonprescription drugs at present, is listed as the large pillar product of antipyretic and analgesic three together with acetylsalicylic acid, Paracetamol.In China, be mainly used in the aspects such as pain relieving, rheumatism, and not many in flu, application aspect bringing down a fever, well below Paracetamol and acetylsalicylic acid.The pharmaceutical manufacturer that China holds Motrin production approval number reaches tens, but " Fenbid " slow releasing capsule that the overwhelming majority of domestic market Ibuprofen BP/EP sales volume is produced by Tianjin Sino-U.S. SmithKline company is occupied.
Ibuprofen BP/EP is the team by Stewart doctor Adams (became afterwards and teach and win English kingdom medal) and its leader---scientific research expert CoLinBurrows, the common discovery of chemist John doctor Nicholson.The object of original research is invention a kind of " super acetylsalicylic acid ", thereby obtains a kind of and therapeutic effect of aspirin quite but the alternative medicine of serious adverse reaction treatment rheumatoid arthritis still less.And other drug, as Phenylbutazone, the danger that granulopenia occurs is very high; Corticosteroids, when using dosage is slightly higher than ordinary recipe dosage, bring suprarenal gland to suppress and other untoward reaction as the high risk of gastrointestinal ulceration etc.Adams determine to find a kind of medicine with good gi tract tolerance, this characteristic particularly important all concerning at present all on-steroidal AIDs.
Phenylacetate class medicine has caused people's interest.Although find in the test of dog, some this type of medicine has the danger of the ulcer of causing, and Adams recognizes, this phenomenon may be long the causing of transformation period of removing due to medicine.In this class medicine, there is a kind of compound---the transformation period of Ibuprofen BP/EP is shorter, only 2 hours.In screening alternative medicine out, although be not the most effective, be safest.Within 1964, Ibuprofen BP/EP becomes the most rising acetylsalicylic acid alternative medicine.
At present, the medicinal use of Ibuprofen BP/EP mainly comprises: 1, alleviate the acute attack stage of various chronic arthritiss or the arthralgia symptoms of persistence such as rheumatoid arthritis, osteoarthritis, SpA, urarthritis, rheumatic arthritis, without the effect of etiological treatment and the control course of disease.2, treat non-arthrogenous various soft tissue rheumatism pain, as shoulder pain, tenosynovitis, bursitis, myalgia and the rear damaging pain of motion etc.3, acute light, moderate pain as: after operation, after wound, after strain, primary dysmenorrhoea, toothache, headache etc.4, adult and children's heating is had to refrigeration function.
CN201210328660.3 discloses a kind of process for purification of Ibuprofen BP/EP, and this process for purification comprises the following steps: Ibuprofen BP/EP crude product, add organic solvent, and heating, is cooled to room temperature, and refrigeration crystallization, then repeats step above 2-5 time.Method provided by the invention can make highly purified highly finished product, and with low cost, the Ibuprofen BP/EP purity making reaches more than 99.5%, very effectively improved Ibuprofen BP/EP purity, finally obtained a kind of Ibuprofen BP/EP compound of high purity injection stage, thereby safe injection raw material is provided.
CN201210397836.0 discloses a kind of process for purification of Ibuprofen BP/EP, be specifically related to a kind of Ibuprofen BP/EP process for refining, limit of impurities and with the quality contrast of current commercially available Ibuprofen BP/EP, belong to medical technical field.It is got Ibuprofen BP/EP and mainly uses organic solvent dissolution, by adding gac reflux decolour to obtain the Ibuprofen BP/EP after finished product is refined by crystallization, filtration, grinding, dry weighing.The product that the present invention is prepared, the foreign matter content of Ibuprofen BP/EP can be strict controlled in certain limit, can meet all formulation requirements that comprise injection, when making it to patient's intravenous drip and passing through other administration route, as much as possible avoid to property human body to produce untoward reaction, security is higher.Ibuprofen BP/EP process for refining described in the present invention is simple, easy to operate, efficiency is high, can make stay-in-grade product.
CN200910042425.8 discloses a kind of preparation method of Ibuprofen BP/EP, take isobutyl-benzene as raw material, through Friedel-Crafts reaction, generate 4-isobutyl acetophenone, through epoxidation, generate 2-(4-isobutyl phenenyl)-1 again, 2-propylene oxide, under LEWIS acid catalysis, intramolecular rearrangement obtains 1-(4-isobutyl phenenyl) propionic aldehyde, by hydrogen peroxide oxidation, obtains Ibuprofen BP/EP.This preparation method does not use noble metal catalyst, and solvent used adapts to industrial requirement, has the advantages such as raw material is cheap, technique is simple, reaction conditions is gentle, yield is high, quantity of three wastes is few.
The stability of above-mentioned patent and other Ibuprofen BP/EP of the prior art is poor, stores for a long time, and its related substances in Ibuprofen BP/EP raises very fast, in order to obtain the better Ibuprofen BP/EP of a kind of stability, and special proposition the present invention.
Summary of the invention
The first object of the present invention is to provide a kind of Ibuprofen BP/EP compound, and this Ibuprofen BP/EP compound has better stability in storage, has greatly improved patient's drug safety.
The present invention's the second object is to provide a kind of preparation method of above-mentioned Ibuprofen BP/EP compound.
The 3rd object of the present invention is to provide a kind of pharmaceutical composition that contains above-mentioned Ibuprofen BP/EP compound.
In order to realize foregoing invention object, the present invention takes following technical scheme:
An Ibuprofen BP/EP compound, the structural formula of described Ibuprofen BP/EP compound is as follows:
The X-ray powder diffraction spectrogram that described Ibuprofen BP/EP compound use Cu-K alpha-ray measures as shown in Figure 1.
The inside solid-state structure of compound has very large impact to its physicochemical property, same compound, its crystal formation is different, cause its lattice energy different, thereby cause its physicals also different, so the compound of different crystal formations, thereby its lattice causes its stability also different to the difference of the binding force size of molecule.
The invention provides the different Ibuprofen BP/EP of a kind of and above-mentioned crystal formation, compare and have higher lattice energy with the Ibuprofen BP/EP of prior art, lattice is bound stronger to Ibuprofen BP/EP molecule, thereby has improved the stability of Ibuprofen BP/EP compound.Contriver is by stability experiment, and result shows that the special crystallized form of Ibuprofen BP/EP compound provided by the present invention compares with the solid form of the Ibuprofen BP/EP of prior art, has stronger stability in storage, and this has greatly improved patient's drug safety.
A kind of preparation method of described Ibuprofen BP/EP compound, described preparation method comprises Ibuprofen BP/EP bulk drug is dissolved in the acetone soln of 50-60 ℃, make saturated solution, the ethanol that slowly adds 50-60 ℃, the volumetric usage of ethanol is 1/4～1/6 of acetone volume, and insulated and stirred 30-60 minute carries out magnetic treatment by solution, in the solution of handling, add decolorizing with activated carbon, filter, obtain settled solution, in settled solution, drip water, be cooled to 0-5 ℃, filter, obtain filter cake, washing leaching cake, drying under reduced pressure 2～4h, obtains faint yellow microcrystal powder again.
In order to obtain a kind of brand-new crystal formation of Ibuprofen BP/EP, contriver has done a large amount of experiments, comprise continuous change crystallization method and comprise the crystallization conditions such as pressure, temperature, solvent, pH, anti-solvent, finally obtained a kind of Ibuprofen BP/EP compound with brand-new crystal formation, its X-RD spectrogram shows, the solid interior molecular structure of Ibuprofen BP/EP compound provided by the invention is different from Ibuprofen BP/EP compound of the prior art.
In above-mentioned preparation method, preferred, the volume of described water and the volume ratio of acetone are 8-15:1.
In above-mentioned preparation method, preferred, described magnetic treatment is: solution is flowed through to the direct magnetic field of 0.5T with the speed of 8～15m/s, field direction is vertical with flow of solution direction.
The described decolorizing with activated carbon that adds is this area common technology means, can process referring to any decolouring, those skilled in the art are without paying any creative work, and the prior art that can grasp according to himself is carried out appropriate selection, and realizes the object of the invention.
In above-mentioned preparation method, preferred, the amount that adds gac is the 0.2-0.3%g/ml of liquid cumulative volume.
The present invention also provides a kind of pharmaceutical composition that contains described Ibuprofen BP/EP compound.
Pharmaceutical composition of the present invention can be prepared into various formulations, as liquid preparation, solid preparation.
Preferably, described pharmaceutical composition is capsule, tablet, injection.
In the present invention, described ibuprofen capsule, the prescription of tablet all can adopt the prescription of prior art, those skilled in the art are without paying any creative work, and the prior art that can grasp according to himself is carried out appropriate selection, and realizes the object of the invention.
Preferably, described injection comprises injection liquid, sterile powder injection.
Preferably, by weight, described sterile powder injection comprises 400 parts of Ibuprofen BP/EPs, arginine 320-360 part.
Preferred, by weight, described sterile powder injection comprises 400 parts of Ibuprofen BP/EPs, 338 parts of arginine.
Preferably, by weight, described injection liquid comprises 400 parts of Ibuprofen BP/EPs, arginine 320-360 part, water for injection 3600-4200 part.
Preferred, by weight, described injection liquid comprises 400 parts of Ibuprofen BP/EPs, 338 parts of arginine, 4000 parts of waters for injection.
In the present invention, because the solvability of aseptic Ibuprofen BP/EP in water for injection is very little, therefore when preparing ibuprofen injection and Ibuprofen BP/EP sterile powder injection, need to add arginine as solubility promoter and stablizer, said composition can be dissolved in water for injection in use in specific time.In addition, after adding arginine, can also regulate the pH value of aseptic Ibuprofen BP/EP, make its pH value in Human Tolerance scope.Researchist finds through experiment, Ibuprofen BP/EP and arginic amount ranges in injection liquid of the present invention and sterile powder injection, can make aseptic Ibuprofen BP/EP well dissolve, can make again its pH value in suitable scope, and the clarity of prepared ibuprofen injection and stability better, prepared Ibuprofen BP/EP sterile powder injection stability is better, the clarity after redissolving is better.
In the present invention, described ibuprofen capsule, tablet, injection liquid, sterile powder injection all can adopt the preparation method of prior art, those skilled in the art are without paying any creative work, and the prior art that can grasp according to himself is carried out appropriate selection, and realizes the object of the invention.
Compared with prior art, Ibuprofen BP/EP compound provided by the invention and pharmaceutical composition tool thereof have the following advantages:
(1) to store for a long time foreign matter content few for Ibuprofen BP/EP compound of the present invention, and stability in storage is good;
(2) the pharmaceutical composition stability in storage that contains Ibuprofen BP/EP of the present invention is good, and safety performance is higher.
Accompanying drawing explanation
Fig. 1 is the X-powdery diffractometry spectrogram of the Ibuprofen BP/EP compound of the embodiment of the present invention 1 preparation.
Embodiment
With embodiment, technical scheme of the present invention is further described below; by the advantage contributing to technical scheme of the present invention; effect has further to be understood, and embodiment does not limit protection scope of the present invention, and protection scope of the present invention is decided by claim.
Embodiment 1
The preparation of Ibuprofen BP/EP compound:
Ibuprofen BP/EP bulk drug 50g is dissolved in the acetone soln of 60 ℃, make saturated solution, the ethanol that slowly adds 60 ℃, the volumetric usage of ethanol is 1/4 of acetone volume, insulated and stirred 30 minutes, solution is flowed through to the direct magnetic field of 0.5T with the speed of 8m/s, field direction is vertical with flow of solution direction, in the solution of handling, add decolorizing with activated carbon, whip attachment 30min, filter decarburization degerming, the amount that adds gac is the 0.3%g/ml of liquid cumulative volume, obtain settled solution, in settled solution, drip water, the volume of described water and the volume ratio of acetone are 15:1, be cooled to 5 ℃, filter, obtain filter cake, washing leaching cake, drying under reduced pressure 4h again, obtain white micro-crystals powder.Yield 72.8%, HPLC content 99.85%.mp：102-105℃。
Use X-ray powder diffraction spectrogram that Cu-K alpha-ray measures for Fig. 1 shown.
Embodiment 2
The preparation of Ibuprofen BP/EP compound:
Ibuprofen BP/EP bulk drug 50g is dissolved in the acetone soln of 50 ℃, make saturated solution, the ethanol that slowly adds 50 ℃, the volumetric usage of ethanol is 1/6 of acetone volume, insulated and stirred 60 minutes, solution is flowed through to the direct magnetic field of 0.5T with the speed of 15m/s, field direction is vertical with flow of solution direction, in the solution of handling, add decolorizing with activated carbon, whip attachment 30min, filter decarburization degerming, the amount that adds gac is the 0.2%g/ml of liquid cumulative volume, obtain settled solution, in settled solution, drip water, the volume of described water and the volume ratio of acetone are 8:1, be cooled to 0 ℃, filter, obtain filter cake, washing leaching cake, drying under reduced pressure 2h again, obtain white micro-crystals powder.Yield 74.9%, HPLC content 99.91%.mp：102-105℃。
The X-ray powder diffraction figure that uses Cu-K alpha-ray to measure is consistent with the result of embodiment 1.
Embodiment 3
The preparation of Ibuprofen BP/EP sterile powder injection
The Ibuprofen BP/EP 400g, the arginine 320g that under aseptic condition, take embodiment 1 preparation, be placed in solid powder mixer and evenly mix, and gained raw material proceeds to sterile preparation workshop, delicate metering packing, every bottle contains Ibuprofen BP/EP 0.4g, jumps a queue, rolls lid, finished product packing warehouse-in censorship.
Embodiment 4
The preparation of Ibuprofen BP/EP sterile powder injection
The Ibuprofen BP/EP 400g, the arginine 360g that under aseptic condition, take embodiment 1 preparation, be placed in solid powder mixer and evenly mix, and gained raw material proceeds to sterile preparation workshop, delicate metering packing, every bottle contains Ibuprofen BP/EP 0.8g, jumps a queue, rolls lid, finished product packing warehouse-in censorship.
Embodiment 5
The preparation of Ibuprofen BP/EP sterile powder injection
The Ibuprofen BP/EP 400g, the arginine 338g that under aseptic condition, take embodiment 1 preparation, be placed in solid powder mixer and evenly mix, and gained raw material proceeds to sterile preparation workshop, delicate metering packing, every bottle contains Ibuprofen BP/EP 0.4g, jumps a queue, rolls lid, finished product packing warehouse-in censorship.
Embodiment 6
The preparation of ibuprofen injection
In the material-compound tank of 70 ℃ of fresh water for injection of getting 70% preparation total amount after processing, logical nitrogen 60min.Drop into the arginine of recipe quantity, under logical nitrogen protection, stir it is all dissolved.The Ibuprofen BP/EP that adds again recipe quantity, stirring and dissolving under nitrogen protection, adds to the full amount of water for injection, and is uniformly mixed.Fluid temperature is down to 30 ℃, continues logical nitrogen protection.Add preparation total amount 0.05%(g/ml) Medicinal Charcoal to liquid, under nitrogen protection, whip attachment is 20 minutes, decarbonization filtering.With aperture, be the millipore filtration essence filter of 0.45 μ m, visible foreign matters inspection is done in sampling, is delivered to embedding after up to specification.Logical nitrogen embedding: clean and in the 5ml of sterilizing ampoule in common process by specification requirement filling and sealing.121 ℃ of pressure sterilizing 15min.
Embodiment 7
The preparation of ibuprofen injection
In the material-compound tank of 70 ℃ of fresh water for injection of getting 70% preparation total amount after processing, logical nitrogen 60min.Drop into the arginine of recipe quantity, under logical nitrogen protection, stir it is all dissolved.The Ibuprofen BP/EP that adds again recipe quantity, stirring and dissolving under nitrogen protection, adds to the full amount of water for injection, and is uniformly mixed.Fluid temperature is down to 30 ℃, continues logical nitrogen protection.Add preparation total amount 0.05%(g/ml) Medicinal Charcoal to liquid, under nitrogen protection, whip attachment is 20 minutes, decarbonization filtering.With aperture, be the millipore filtration essence filter of 0.45 μ m, visible foreign matters inspection is done in sampling, is delivered to embedding after up to specification.Logical nitrogen embedding: clean and in the 5ml of sterilizing ampoule in common process by specification requirement filling and sealing.121 ℃ of pressure sterilizing 15min.Obtain.
Embodiment 8
The preparation of ibuprofen injection
In the material-compound tank of 80 ℃ of fresh water for injection of getting 70% preparation total amount after processing, logical nitrogen 60min.Drop into the arginine of recipe quantity, under logical nitrogen protection, stir it is all dissolved.The Ibuprofen BP/EP that adds again recipe quantity, stirring and dissolving under nitrogen protection, adds to the full amount of water for injection, and is uniformly mixed.Fluid temperature is down to 40 ℃, continues logical nitrogen protection.Add preparation total amount 0.05%(g/ml) Medicinal Charcoal to liquid, under nitrogen protection, whip attachment is 20 minutes, decarbonization filtering.With aperture, be the millipore filtration essence filter of 0.45 μ m, visible foreign matters inspection is done in sampling, is delivered to embedding after up to specification.Logical nitrogen embedding: clean and in the 10ml of sterilizing ampoule in common process by specification requirement filling and sealing.121 ℃ of pressure sterilizing 15min.
Experimental example 1
This test example detects related substance in the prepared Ibuprofen BP/EP of embodiment 1～2, and this test is carried out according to 2010 editions second appendix VIII P residual solvent assay method of Chinese Pharmacopoeia, appendix XIX F medicine impurity analysis governing principle, and it the results are shown in Table 1:
The assay of table 1 related substance
| Preparation | Acetone | Ethanol | Other related substance |
| Embodiment 1 product | Up to specification | Up to specification | Up to specification |
| Embodiment 2 products | Up to specification | Up to specification | Up to specification |
Experimental example 2
This experimental example has been investigated the stability of Ibuprofen BP/EP provided by the invention
This test is carried out according to 2005 editions second appendix XIX C medicine stability test governing principle of Chinese Pharmacopoeia, and result is as follows:
Table 2, accelerated test assay result
| ? | 0 month | 1 month | 3 months | 6 months | 9 months | 12 months |
| 1 | 100.01% | 100.0% | 99.97% | 99.91% | 99.83% | 99.73% |
| 2 | 99.97% | 99.96% | 99.94% | 99.88% | 99.81% | 99.71% |
| 3 | 99.92% | 99.89% | 99.85% | 99.65% | 98.99% | 98.22% |
| 4 | 99.97% | 99.95% | 99.90% | 99.67% | 98.98% | 98.46% |
Table 3, test of long duration assay result
| ? | 0 month | 3 months | 6 months | 9 months | 15 months | 24 months |
| 1 | 100.01% | 100.0% | 99.96% | 99.90% | 99.83% | 99.72% |
| 2 | 99.97% | 99.96% | 99.93% | 99.85% | 99.80% | 99.70% |
| 3 | 99.92% | 99.90% | 99.84% | 99.62% | 98.97% | 98.42% |
| 4 | 99.97% | 99.96% | 99.92% | 99.65% | 98.95% | 98.25% |
Sample 1 is the product of the embodiment of the present invention 1;
Sample 2 is the product of the embodiment of the present invention 2;
The Ibuprofen BP/EP of sample 3 for preparing with reference to the method for CN201210328660.3 embodiment 1, HPLC is 99.88%;
Sample 4 is commercially available Ibuprofen BP/EP, originates from Hua Yao bio tech ltd, Zhengzhou;
Accelerated test and test of long duration by this experimental example are known, and compared with prior art, the stability of Ibuprofen BP/EP compound provided by the invention is better.
Experimental example 3
This experimental example is the influence factor test of ibuprofen injection provided by the invention
Ibuprofen injection prepared by embodiment 6 and embodiment 7 is respectively at placing 10 days under 60 ℃ of high temperature, illumination 4500lx ± 500lx, 4 ℃ of conditions of low temperature, respectively at sampling in the 5th, 10 days, investigate proterties, pH value, related substance, visible foreign matters, the content of ibuprofen injection, the stability of prescription is determined in checking.The influence factor test-results of the ibuprofen injection that the influence factor test-results of the ibuprofen injection of embodiment 6 preparations is prepared in Table 4, embodiment 7 is in Table 5.
Table 4 influence factor testing data
Table 5 influence factor testing data
Conclusion: test-results shows, ibuprofen injection provided by the invention is placed after 10 days 60 ℃ of high temperature, with 0 day relatively, every quality index has no significant change; This product is placed after 10 days under illumination 4500lx ± 500lx, 4 ℃ of conditions of low temperature, and with comparison in 0 day, every quality index had no significant change.As can be seen here, this product, under hot conditions and under cold condition, all has extraordinary stability.
Claims (10)
1. an Ibuprofen BP/EP compound, is characterized in that, the structural formula of described Ibuprofen BP/EP compound is as follows:
The X-ray powder diffraction spectrogram that described Ibuprofen BP/EP compound use Cu-K alpha-ray measures as shown in Figure 1.
2. the preparation method of an Ibuprofen BP/EP compound claimed in claim 1, it is characterized in that, described preparation method comprises Ibuprofen BP/EP bulk drug is dissolved in the acetone soln of 50-60 ℃, make saturated solution, the ethanol that slowly adds 50-60 ℃, the volumetric usage of ethanol is 1/4～1/6 of acetone volume, insulated and stirred 30-60 minute, solution is carried out to magnetic treatment, in the solution of handling, add decolorizing with activated carbon, filter, obtain settled solution, in settled solution, drip water, be cooled to 0-5 ℃, filter, obtain filter cake, washing leaching cake, drying under reduced pressure 2～4h again, obtain faint yellow microcrystal powder.
3. preparation method according to claim 2, is characterized in that, the volume of described water and the volume ratio of acetone are 8-15:1.
4. preparation method according to claim 3, is characterized in that, described magnetic treatment is: solution is flowed through to the direct magnetic field of 0.5T with the speed of 8～15m/s, field direction is vertical with flow of solution direction.
5. a pharmaceutical composition that contains Ibuprofen BP/EP compound claimed in claim 1.
6. pharmaceutical composition according to claim 5, is characterized in that, described pharmaceutical composition is capsule, tablet, injection.
7. pharmaceutical composition according to claim 6, is characterized in that, described injection comprises injection liquid, sterile powder injection.
8. pharmaceutical composition according to claim 7, is characterized in that, by weight, described sterile powder injection comprises 400 parts of Ibuprofen BP/EPs, arginine 320-360 part.
9. pharmaceutical composition according to claim 7, is characterized in that, by weight, described injection liquid comprises 400 parts of Ibuprofen BP/EPs, arginine 320-360 part, water for injection 3600-4200 part.
10. pharmaceutical composition according to claim 9, is characterized in that, by weight, described injection liquid comprises 400 parts of Ibuprofen BP/EPs, 338 parts of arginine, 4000 parts of waters for injection.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102408288A (en) * | 2011-08-10 | 2012-04-11 | 天津市天地创智科技发展有限公司 | Method for separating chiral drug by using protein-functionalized magnetic nanoparticles |
| CN102408289A (en) * | 2011-08-10 | 2012-04-11 | 天津市天地创智科技发展有限公司 | Separation method of chiral medicament by applying protein functionalized magnetic nano-particles |
| CN102727443A (en) * | 2012-06-29 | 2012-10-17 | 陈士忠 | Clathrate of mesoporous silicon oxide/Fe3O4 magnetic nano-grade complex and ibuprofen |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102408288A (en) * | 2011-08-10 | 2012-04-11 | 天津市天地创智科技发展有限公司 | Method for separating chiral drug by using protein-functionalized magnetic nanoparticles |
| CN102408289A (en) * | 2011-08-10 | 2012-04-11 | 天津市天地创智科技发展有限公司 | Separation method of chiral medicament by applying protein functionalized magnetic nano-particles |
| CN102727443A (en) * | 2012-06-29 | 2012-10-17 | 陈士忠 | Clathrate of mesoporous silicon oxide/Fe3O4 magnetic nano-grade complex and ibuprofen |
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