CN103204774A - 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 the Isobuytel Benzene propyl alcohol, is the nonsteroidal antiinflammatory and analgesic medicine.Its anti-inflammatory, analgesia, refrigeration function are respond well, and untoward reaction is less.Widespread use in the world at present becomes one of global best-selling nonprescription drugs and acetylsalicylic acid, Paracetamol and is listed as antipyretic and analgesic three big pillar products together.Be mainly used in aspects such as pain relieving, rheumatism in China, and the application aspect catching a cold, bringing down a fever is not many, well below Paracetamol and acetylsalicylic acid.The pharmaceutical manufacturer that China holds Motrin production authentication code reaches tens families, but the overwhelming majority of domestic market Ibuprofen BP/EP sales volume is occupied by " Fenbid " slow releasing capsule that Tianjin Sino-U.S. SmithKline company produces.
Ibuprofen BP/EP is the team by Stewart doctor Adams (became professor afterwards and won English kingdom medal) and its leader---scientific research expert CoLinBurrows, the common discovery of chemist John doctor Nicholson.The purpose of original research is invention a kind of " super acetylsalicylic acid ", thereby obtains a kind of and acetylsalicylic acid therapeutic equivalence but the alternative medicine of serious adverse reaction treatment rheumatoid arthritis still less.And other drug, as Phenylbutazone, the danger that granulopenia takes place is very high; Corticosteroids when using dosage is higher slightly than ordinary recipe dosage, is then brought the high risk of suprarenal gland inhibition and other untoward reaction such as gastrointestinal ulceration etc.Adams determine to seek 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.Though find in the test of dog, some this type of medicine has the danger of the ulcer of causing, and Adams recognizes that this phenomenon may be because long the causing of transformation period that medicine is removed.In this class medicine, a kind of compound being arranged---the transformation period of Ibuprofen BP/EP is shorter, only 2 hours.In the alternative medicine that screening is come out, though be not the most effective, be safest.Ibuprofen BP/EP became the most rising acetylsalicylic acid alternative medicine in 1964.
At present, the medicinal use of Ibuprofen BP/EP mainly comprises: 1, alleviate the acute attack stage of various chronic arthritiss such as rheumatoid arthritis, osteoarthritis, SpA, urarthritis, rheumatic arthritis or the arthralgia symptom of persistence, anosis effect because for the treatment of and the control course of disease.2, the non-arthrogenous various soft tissue rheumatism pain for the treatment of are as shoulder pain, tenosynovitis, bursitis, the damaging pain of myalgia and motion back etc.3, acute light, moderate pain as: after operation back, the wound, strain back, primary dysmenorrhoea, toothache, headache etc.4, the heating to adult and children has refrigeration function.
CN201210328660.3 discloses a kind of process for purification of Ibuprofen BP/EP, and this process for purification may further comprise the steps: the Ibuprofen BP/EP crude product, add organic solvent, and heating is cooled to room temperature, and the refrigeration crystallization repeats step 2-5 time of front then.Method provided by the invention can make highly purified highly finished product, and it is with low cost, the Ibuprofen BP/EP purity that makes reaches more than 99.5%, improved Ibuprofen BP/EP purity very effectively, 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 present commercially available Ibuprofen BP/EP, belong to medical technical field.It is got Ibuprofen BP/EP and mainly uses organic solvent dissolution, weighs by crystallization, filtration, grinding, drying and obtains the Ibuprofen BP/EP of finished product after refining by adding the gac reflux decolour.The product that the present invention is prepared, the foreign matter content of Ibuprofen BP/EP can be strict controlled in the 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 is produced untoward reaction, security is higher.Ibuprofen BP/EP process for refining described in the present invention is simple, easy to operate, efficient is high, can make stay-in-grade product.
CN200910042425.8 discloses a kind of preparation method of Ibuprofen BP/EP, be raw material with the isobutyl-benzene, generate the 4-isobutyl acetophenone through Friedel-Crafts reaction, generate 2-(4-isobutyl phenenyl)-1 through epoxidation again, the 2-propylene oxide, intramolecular rearrangement obtains 1-(4-isobutyl phenenyl) propionic aldehyde under the LEWIS acid catalysis, gets Ibuprofen BP/EP by hydrogen peroxide oxidation.This preparation method does not use noble metal catalyst, and used solvent adapts to industrial requirement, has advantages such as raw material is cheap, technology is simple, reaction conditions is gentle, yield is high, quantity of three wastes is few.
Above-mentioned patent and other Ibuprofen BP/EP of the prior art stable poor, the long-time storage, its related substances in the Ibuprofen BP/EP raises very fast, in order to obtain the better Ibuprofen BP/EP of a kind of stability, specially proposes the present invention.
Summary of the invention
First purpose 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 second purpose is to provide a kind of preparation method of above-mentioned Ibuprofen BP/EP compound.
The 3rd purpose of the present invention is to provide a kind of pharmaceutical composition that contains above-mentioned Ibuprofen BP/EP compound.
In order to realize the foregoing invention purpose, the present invention takes following technical scheme:
A kind of 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 influence to its physicochemical property, with a kind of compound, its crystal formation difference, cause its lattice energy difference, 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 with the Ibuprofen BP/EP of prior art and have higher lattice energy, lattice is bound stronger to the Ibuprofen BP/EP molecule, thereby has improved the stability of Ibuprofen BP/EP compound.The contriver is by stability experiment, and the 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 the Ibuprofen BP/EP bulk drug is dissolved in 50-60 ℃ the acetone soln, 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 magnetic treatment, add decolorizing with activated carbon in the solution of handling, 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 namely gets faint yellow microcrystal powder again.
In order to obtain a kind of brand-new crystal formation of Ibuprofen BP/EP, the contriver has done a large amount of experiments, comprise continuous change crystallization method and comprise 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 that the solid interior molecular structure of Ibuprofen BP/EP compound provided by the invention is different with Ibuprofen BP/EP compound of the prior art.
Among the above-mentioned preparation method, preferred, the volume of described water and the volume ratio of acetone are 8-15:1.
Among the above-mentioned preparation method, preferred, described magnetic treatment is: solution is flowed through the direct magnetic field of 0.5T with the speed of 8～15m/s, and field direction is vertical with the flow of solution direction.
Described adding decolorizing with activated carbon is this area common technology means, can handle referring to any decolouring, those skilled in the art need not to pay any creative work, can carry out appropriate selection according to the prior art of himself grasping, and realize the object of the invention.
Among the above-mentioned preparation method, preferred, the amount that adds gac is the 0.2-0.3%g/ml of soup 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.
Among the present invention, the prescription of described ibuprofen capsule, tablet all can adopt the prescription of prior art, those skilled in the art need not to pay any creative work, can carry out appropriate selection according to the prior art of himself grasping, and realize 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 preparation ibuprofen injection and Ibuprofen BP/EP sterile powder injection, need to add arginine as solubility promoter and stablizer, make said composition can in specific time, be dissolved in the water for injection in use.In addition, add after the arginine, the pH value that can also regulate aseptic Ibuprofen BP/EP makes its pH value be in the human body tolerance range.The researchist finds through experiment, Ibuprofen BP/EP and arginic amount ranges in injection liquid of the present invention and the sterile powder injection, aseptic Ibuprofen BP/EP is well dissolved, can make its pH value be in suitable scope again, and the clarity of prepared ibuprofen injection and stability are better, and prepared Ibuprofen BP/EP sterile powder injection stability is better, the clarity after redissolving is better.
Among 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 need not to pay any creative work, can carry out appropriate selection according to the prior art of himself grasping, and realize the object of the invention.
Compared with prior art, Ibuprofen BP/EP compound provided by the invention and pharmaceutical composition thereof have following advantage:
(1) to store foreign matter content for a long time 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.
Description of drawings
Fig. 1 is the X-powdery diffractometry spectrogram of the Ibuprofen BP/EP compound of the embodiment of the invention 1 preparation.
Embodiment
Below with embodiment technical scheme of the present invention is further described; to help the advantage 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 60 ℃ the acetone soln, 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 the direct magnetic field of 0.5T with the speed of 8m/s, and field direction is vertical with the flow of solution direction, adds decolorizing with activated carbon in the solution of handling, whip attachment 30min, filter the decarburization degerming, the amount that adds gac is the 0.3%g/ml of soup cumulative volume, obtains settled solution, in settled solution, drip water, the volume of described water and the volume ratio of acetone are 15:1, are cooled to 5 ℃, filter, obtain filter cake, washing leaching cake, drying under reduced pressure 4h namely gets the white micro-crystals powder again.Yield 72.8%, HPLC content 99.85%.mp：102-105℃。
The X-ray powder diffraction spectrogram that uses the Cu-K alpha-ray to measure is shown as Fig. 1.
Embodiment 2
The preparation of Ibuprofen BP/EP compound:
Ibuprofen BP/EP bulk drug 50g is dissolved in 50 ℃ the acetone soln, 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 the direct magnetic field of 0.5T with the speed of 15m/s, and field direction is vertical with the flow of solution direction, adds decolorizing with activated carbon in the solution of handling, whip attachment 30min, filter the decarburization degerming, the amount that adds gac is the 0.2%g/ml of soup cumulative volume, obtains settled solution, in settled solution, drip water, the volume of described water and the volume ratio of acetone are 8:1, are cooled to 0 ℃, filter, obtain filter cake, washing leaching cake, drying under reduced pressure 2h namely gets the white micro-crystals powder again.Yield 74.9%, HPLC content 99.91%.mp：102-105℃。
The X-ray powder diffraction figure that uses the 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
Take by weighing Ibuprofen BP/EP 400g, the arginine 320g of embodiment 1 preparation under aseptic condition, place the pressed powder mixing machine evenly to mix, the gained raw material changes the sterile preparation workshop over to, the delicate metering packing, every bottle contains Ibuprofen BP/EP 0.4g, jumps a queue, rolls lid, finished product packing warehouse-in and censorship.
Embodiment 4
The preparation of Ibuprofen BP/EP sterile powder injection
Take by weighing Ibuprofen BP/EP 400g, the arginine 360g of embodiment 1 preparation under aseptic condition, place the pressed powder mixing machine evenly to mix, the gained raw material changes the sterile preparation workshop over to, the delicate metering packing, every bottle contains Ibuprofen BP/EP 0.8g, jumps a queue, rolls lid, finished product packing warehouse-in and censorship.
Embodiment 5
The preparation of Ibuprofen BP/EP sterile powder injection
Take by weighing Ibuprofen BP/EP 400g, the arginine 338g of embodiment 1 preparation under aseptic condition, place the pressed powder mixing machine evenly to mix, the gained raw material changes the sterile preparation workshop over to, the delicate metering packing, every bottle contains Ibuprofen BP/EP 0.4g, jumps a queue, rolls lid, finished product packing warehouse-in and censorship.
Embodiment 6
The preparation of ibuprofen injection
Get in the material-compound tank of 70 ℃ of fresh water for injection after handling of 70% preparation total amount logical nitrogen 60min.Drop into the arginine of recipe quantity, under logical nitrogen protection, stir and make its whole dissolvings.The Ibuprofen BP/EP that adds recipe quantity again, stirring and dissolving under nitrogen protection adds to the full amount of water for injection, and mixes.Fluid temperature is down to 30 ℃, continues logical nitrogen protection.Adding preparation total amount 0.05%(g/ml) Medicinal Charcoal is to soup, and whip attachment is 20 minutes under nitrogen protection, decarbonization filtering.Be the smart filter of millipore filtration of 0.45 μ m with the aperture, the visible foreign matters inspection is done in sampling, is delivered to embedding after up to specification.Logical nitrogen embedding: clean and in the 5ml ampoule of sterilization in common process by the specification requirement filling and sealing.121 ℃ of pressure sterilizing 15min.
Embodiment 7
The preparation of ibuprofen injection
Get in the material-compound tank of 70 ℃ of fresh water for injection after handling of 70% preparation total amount logical nitrogen 60min.Drop into the arginine of recipe quantity, under logical nitrogen protection, stir and make its whole dissolvings.The Ibuprofen BP/EP that adds recipe quantity again, stirring and dissolving under nitrogen protection adds to the full amount of water for injection, and mixes.Fluid temperature is down to 30 ℃, continues logical nitrogen protection.Adding preparation total amount 0.05%(g/ml) Medicinal Charcoal is to soup, and whip attachment is 20 minutes under nitrogen protection, decarbonization filtering.Be the smart filter of millipore filtration of 0.45 μ m with the aperture, the visible foreign matters inspection is done in sampling, is delivered to embedding after up to specification.Logical nitrogen embedding: clean and in the 5ml ampoule of sterilization in common process by the specification requirement filling and sealing.121 ℃ of pressure sterilizing 15min.Namely.
Embodiment 8
The preparation of ibuprofen injection
Get in the material-compound tank of 80 ℃ of fresh water for injection after handling of 70% preparation total amount logical nitrogen 60min.Drop into the arginine of recipe quantity, under logical nitrogen protection, stir and make its whole dissolvings.The Ibuprofen BP/EP that adds recipe quantity again, stirring and dissolving under nitrogen protection adds to the full amount of water for injection, and mixes.Fluid temperature is down to 40 ℃, continues logical nitrogen protection.Adding preparation total amount 0.05%(g/ml) Medicinal Charcoal is to soup, and whip attachment is 20 minutes under nitrogen protection, decarbonization filtering.Be the smart filter of millipore filtration of 0.45 μ m with the aperture, the visible foreign matters inspection is done in sampling, is delivered to embedding after up to specification.Logical nitrogen embedding: clean and in the 10ml ampoule of sterilization in common process by the 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 of Chinese Pharmacopoeia residual solvent assay method, 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 of Chinese Pharmacopoeia medicine stability test governing principle, and the 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 invention 1;
Sample 2 is the product of the embodiment of the invention 2;
Sample 3 is that HPLC is 99.88% with reference to the Ibuprofen BP/EP of the method preparation of CN201210328660.3 embodiment 1;
Sample 4 is commercially available Ibuprofen BP/EP, originates from Zhengzhou China credit bio tech ltd;
Accelerated test by this experimental example and test of long duration as can be known, 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
With the ibuprofen injection of embodiment 6 and embodiment 7 preparations 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 day, 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 that the influence factor test-results of the ibuprofen injection of embodiment 6 preparations sees Table the ibuprofen injection of 4, embodiment, 7 preparations sees Table 5.
Table 4 influence factor testing data
Table 5 influence factor testing data
Conclusion: test-results shows that ibuprofen injection provided by the invention is after 60 ℃ of high temperature are placed 10 days, and with comparison in 0 day, every quality index had no significant change; This product is after placing 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.This shows that this product all has extraordinary stability under hot conditions and under the cold condition.
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 the described Ibuprofen BP/EP compound of claim 1, it is characterized in that, described preparation method comprises the Ibuprofen BP/EP bulk drug is dissolved in 50-60 ℃ the acetone soln, make saturated solution, slowly add 50-60 ℃ ethanol, the volumetric usage of ethanol is 1/4～1/6 of acetone volume, insulated and stirred 30-60 minute, solution is carried out magnetic treatment, add decolorizing with activated carbon in the solution of handling, 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 namely gets faint yellow microcrystal powder again.
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 the direct magnetic field of 0.5T with the speed of 8～15m/s, and field direction is vertical with the flow of solution direction.
5. pharmaceutical composition that contains the described Ibuprofen BP/EP compound of 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 |
|---|---|---|---|---|
| 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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