CN105343006A - Nanometer framework system for carrying indissolvable medicines, as well as preparation and application of nanometer framework system - Google Patents
Nanometer framework system for carrying indissolvable medicines, as well as preparation and application of nanometer framework system Download PDFInfo
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- CN105343006A CN105343006A CN201510870096.1A CN201510870096A CN105343006A CN 105343006 A CN105343006 A CN 105343006A CN 201510870096 A CN201510870096 A CN 201510870096A CN 105343006 A CN105343006 A CN 105343006A
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
- A61K9/146—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with organic macromolecular compounds
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/337—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having four-membered rings, e.g. taxol
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4745—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
- A61K9/143—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with inorganic compounds
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Abstract
The invention relates to a nanometer framework system for carrying indissolvable medicines, as well as preparation and application of the nanometer framework system. The nanometer framework system comprises (1) one or more indissolvable medicines, (2) nanometer framework material mesoporous silicon dioxide, (3) any existent polymer dispersed material HPMC and (4) an amphipathic material DSPE-PEG. The one or more indissolvable medicines is/are selected from one or more of taxane antineoplastic medicines, camptothecin antineoplastic medicines, antibiotic antineoplastic medicines and sorafenib. The solubleness, the dissolution rate, the bioavailability and the tumor inhibition rate of the indissolvable medicines are greatly improved, and the indissolvable medicines are less in toxic and side effects and good in tolerance, can be used as preparations of oral medication, are strong in compliance, and can achieve the purpose of effectively treating the tumor.
Description
Technical field
The present invention relates to pharmaceutical carrier and field of nanometer technology, being specifically related to a kind of nano bone frame system for carrying insoluble drug and its production and use.
Background technology
In antitumor drug treatment, medicine slightly solubility is an obstacle hindering medicine effectively to send all the time.So find a kind of new medicament carrier system, increasing the dissolubility of insoluble drug, significantly improving bioavailability thus strengthen oncotherapy effect, alleviate toxic and side effects is the major issue that current medicament is studied.
Nano material is widely applied in the middle of insoluble drug solubilising strategy as pharmaceutical carrier.Wherein, the nanometer skeleton being representative with mesoporous silicon oxide particle is due to its good biocompatibility, preferably aperture rate, larger specific surface area and preferably stability, there is the homogeneous mesoporous pore size that can regulate continuously within the scope of 2-50nm, stable framing structure simultaneously, be suitable as very much the carrier of medicine.
Meanwhile, polymer (HPMC) can play the effect increasing dissolution and suppress crystal to produce in solid dispersion system, and the dissolubility that DSPE-PEG increases medicine as amphipathic nature material by the mode that adipose membrane wraps up also is widely used.
Summary of the invention
The present invention is according to current research present situation, provides that a kind of combining nano skeleton, polymeric dispersions, amphipathic nature material advantage are strong in the stability of one, drug loading is high and solubilising amplitude is larger carries nano bone frame system of insoluble drug and its preparation method and application.
First aspect present invention relates to the nano bone frame system carrying insoluble drug, comprise (1) one or more insoluble drugs, (2) nano bone frame material mesoporous silicon oxide, (3) the optional polymer dispersed material HPMC existed, and (4) amphipathic nature material DSPE-PEG.
Wherein, the quality of described insoluble drug and mesoporous silicon oxide is 1:1-5 than scope, and/or the quality of described insoluble drug and HPMC is 1:0-5 than scope, and/or the quality of described insoluble drug and DSPE-PEG is 1:1-5 than scope.
Preferably, the ratio of described insoluble drug, mesoporous silicon oxide, HPMC, DSPE-PEG is 1:3:0:3,1:3:1.5:1.5 or 1:3:3:3, most preferably is 1:3:3:3.
Described insoluble drug refers to insoluble or microsolubility medicine well known in the art, and such as it is less than 1g at the dissolubility of 20 DEG C of described medicines in water, or is less than 0.1g, or is less than 0.01g.
Described insoluble drug is selected from: one or more in yew alkanes, camptothecin, antibiotics antineoplastic agent, BAY 43-9006.
Described yew alkanes comprises paclitaxel, Docetaxel, Cephalomannine, 10-go acetyl baccatin III, 7-difference to paclitaxel etc.
Described camptothecin comprises camptothecine, SN38 (SN38), 9-dimethylamine methyl isophthalic acid 0-hydroxy camptothecin, irenotecan, 9-aminocamptothecin, 9-nitrocamptothecin, GI147211, DX-8951f etc.
Described antibiont series antineoplastic medicament is selected from amycin, epirubicin etc.
Preferably, described insoluble drug is BAY 43-9006, paclitaxel and/or SN38 (SN38).
Most preferably, described insoluble drug is BAY 43-9006.
Described DSPE-PEG is preferably DSPE-PEG
2000.
Second aspect present invention relates to the preparation method of the nano bone frame system carrying insoluble drug, and described method comprises the steps:
1) mesoporous silicon oxide of recipe quantity is distributed in dichloromethane, under magnetic stirring, adds the insoluble drug of the recipe quantity being dissolved in organic solvent, obtain mixture 1.;
2) HPMC of recipe quantity is scattered in dichloromethane, for mixture 2.;
1. and 2. 3) by mixture respectively simultaneously after ultrasonic 20-40min, under magnetic stirring, 2. mixture is added drop-wise to mixture 1. in and Keep agitation 24h, obtain mixture 3.;
4) 4. the organic solvent that reduction vaporization removing dichloromethane and insoluble drug are dissolved under the condition of 30-50 DEG C (preferably 40 DEG C), obtain mixture;
5), after the DSPE-PEG of recipe quantity being dissolved in dichloromethane, being joined and mixture revolving 4. is housed steams in bottle, ultrasonic 15min;
6) reduction vaporization under the condition of 30-50 DEG C (preferably 40 DEG C), collects solid, pulverizes and obtain the nano bone frame system carrying insoluble drug.
Described preparation method step 1 of carrying the nano bone frame system of insoluble drug) in the organic solvent that is dissolved in of insoluble drug be methanol, ethanol or acetonitrile.
A third aspect of the present invention relates to the nano bone frame system carrying insoluble drug and is preparing the application in antitumor drug.
Described tumor is selected from solid tumor or non-physical tumor, such as hepatocarcinoma, pulmonary carcinoma, gastric cancer, renal carcinoma, breast carcinoma, cervical cancer, lymphoma, leukemia.
A fourth aspect of the present invention relates to the pharmaceutical composition comprising the nano bone frame system carrying insoluble drug.
Described pharmaceutical composition can be pharmaceutically acceptable any dosage form, preferred oral preparation.
Advantage of the present invention:
On the one hand, the present invention is based on the high drug load of mesoporous silicon dioxide nano framework material, high stability and safety preferably, the nano bone frame system carrying insoluble drug prepared in conjunction with polymer dispersed material HPMC and the solubilization of amphipathic nature material DSPE-PEG of FDA approval significantly can improve the dissolubility of insoluble drug, dissolution, bioavailability and tumor control rate, and toxic and side effects is little, there is good toleration, simultaneously can as the preparation of oral administration, its compliance is strong, can reach the object of effective oncotherapy.
On the other hand, the nano bone frame system of of the present invention year insoluble drug also has the advantage that preparation method is simple, material is easy to get, can expand preparation output further.
Accompanying drawing explanation
The dissolubility picture of Fig. 1 BAY 43-9006 crude drug and embodiment 1-3
The dissolubility picture of Fig. 2 paclitaxel api and embodiment 4
The dissolubility picture of Fig. 3 SN38 crude drug and embodiment 5
Fig. 4 normal saline, BAY 43-9006, embodiment 1 nano bone frame system and blank nano bone frame system MDA-MB-231 human breast carcinoma dystopy inoculation Model Tumor volume growth curve
Detailed description of the invention
Embodiment 1
Prescription
Preparation method: be scattered in by the mesoporous silicon oxide of 30mg in 3ml dichloromethane, under magnetic stirring, drips 1ml BAY 43-9006 methanol solution (10mg/ml), obtains BAY 43-9006-mesoporous silicon oxide mixture; The HPMC of 30mg is scattered in 10ml dichloromethane, obtains HPMC-dichloromethane solution; The while of by BAY 43-9006-mesoporous silicon oxide mixture, HPMC-dichloromethane solution (30mg/10ml) respectively after ultrasonic 30min, HPMC-dichloromethane solution is added drop-wise in BAY 43-9006-mesoporous silicon oxide mixture under stirring; Fully stir 24h under room temperature, the rotary evaporation that reduces pressure under 40 DEG C of conditions subsequently volatilizes dichloromethane and methanol, obtains head product; By 30mgDSPE-PEG
2000be dissolved in 3ml dichloromethane and obtain DSPE-PEG
2000dichloromethane solution, by 3mlDSPE-PEG
2000dichloromethane solution (10mg/ml) is added in above-mentioned head product, and after ultrasonic 15min, the same terms revolves steaming, collects solid, pulverizes and obtain the nano bone frame system carrying BAY 43-9006 that mass ratio is 1:3:3:3.
Embodiment 2
Prescription
Preparation method: be scattered in by the mesoporous silicon oxide of 30mg in 3ml dichloromethane, under magnetic stirring, drips 1ml BAY 43-9006 methanol solution (10mg/ml), obtains BAY 43-9006-mesoporous silicon oxide mixture; After BAY 43-9006-ultrasonic 30min of mesoporous silicon oxide mixture, fully stir 24h under room temperature, the rotary evaporation that reduces pressure under 40 DEG C of conditions subsequently volatilizes methylene chloride and methanol, obtains head product; By 30mgDSPE-PEG
2000be dissolved in 3ml dichloromethane and obtain DSPE-PEG
2000dichloromethane solution, by 3mlDSPE-PEG
2000dichloromethane solution (10mg/ml) is added in above-mentioned head product, revolves steaming after ultrasonic 15min with above-mentioned the same terms, collects solid, pulverizes and obtain the nano bone frame system carrying BAY 43-9006 that mass ratio is 1:3:0:3.
Embodiment 3
Prescription
Preparation method: be scattered in 3ml dichloromethane by 30mg mesoporous silicon oxide, under magnetic stirring, drips 1ml BAY 43-9006 methanol solution (10mg/ml), obtains BAY 43-9006-mesoporous silicon oxide mixture; The HPMC of 15mg is scattered in 5ml dichloromethane, obtains HPMC-dichloromethane solution; The while of by BAY 43-9006-mesoporous silicon oxide mixture, HPMC-dichloromethane solution (15mg/5ml) respectively after ultrasonic 30min, HPMC-dichloromethane solution is added drop-wise in BAY 43-9006-mesoporous silicon oxide mixture under stirring; Fully stir 24h under room temperature, the rotary evaporation that reduces pressure under 40 DEG C of conditions subsequently volatilizes methylene chloride and methanol, obtains head product; By 15mgDSPE-PEG
2000be dissolved in 1.5ml dichloromethane and obtain DSPE-PEG
2000dichloromethane solution, by 1.5mlDSPE-PEG
2000dichloromethane solution (10mg/ml) is added in above-mentioned head product, and after ultrasonic 15min, the same terms revolves steaming, collects solid, pulverizes and obtain the nano bone frame system carrying BAY 43-9006 that mass ratio is 1:3:1.5:1.5.
Embodiment 4
Prescription
Preparation method: be scattered in 3ml dichloromethane by 30mg mesoporous silicon oxide, under magnetic stirring, drips 1ml paclitaxel methanol solution (10mg/ml), obtains paclitaxel-mesoporous silicon oxide mixture; The HPMC of 30mg is scattered in 10ml dichloromethane, obtains HPMC-dichloromethane solution; The while of by paclitaxel-mesoporous silicon oxide mixture, HPMC-dichloromethane solution (30mg/10ml) respectively after ultrasonic 30min, HPMC-dichloromethane solution is added drop-wise in paclitaxel-mesoporous silicon oxide mixture under stirring; Fully stir 24h under room temperature, the rotary evaporation that reduces pressure under 40 DEG C of conditions subsequently volatilizes methylene chloride and methanol, obtains head product; By 30mgDSPE-PEG
2000be dissolved in 3ml dichloromethane and obtain DSPE-PEG
2000dichloromethane solution, by 3mlDSPE-PEG
2000dichloromethane solution (10mg/ml) is added in above-mentioned head product, and after ultrasonic 15min, the same terms revolves steaming, collects solid, pulverizes and obtain the nano bone frame system carrying paclitaxel that mass ratio is 1:3:3:3.
Embodiment 5
Prescription
Preparation method: be scattered in 3ml dichloromethane by 30mg mesoporous silicon oxide, under magnetic stirring, drips 1mlSN38 chloroform-methanol (10mg/ml), obtains SN38-mesoporous silicon oxide mixture; The HPMC of 30mg is scattered in 10ml dichloromethane, obtains HPMC-dichloromethane solution; The while of by SN38-mesoporous silicon oxide mixture, HPMC-dichloromethane solution (30mg/10ml) respectively after ultrasonic 30min, HPMC-dichloromethane solution is added drop-wise in SN38-mesoporous silicon oxide mixture under stirring; Fully stir 24h under room temperature, the rotary evaporation that reduces pressure under 40 DEG C of conditions subsequently volatilizes methylene chloride and methanol, obtains head product; By 30mgDSPE-PEG
2000be dissolved in 3ml dichloromethane and obtain DSPE-PEG
2000dichloromethane solution, by 3mlDSPE-PEG
2000dichloromethane solution (10mg/ml) is added in above-mentioned head product, and after ultrasonic 15min, the same terms revolves steaming, collects solid, pulverizes and obtain the nano bone frame system carrying SN38 that mass ratio is 1:3:3:3.
Test example 1 solubility experiment
Get the crude drug and embodiment 1-5 nano bone frame system that are equivalent to 1mg BAY 43-9006, add 1ml pure water, after 37 DEG C of water-baths are vibrated 48 hours, cross the moisture film of 0.45 μm, filtrate measures the concentration of wherein BAY 43-9006 by HPLC.Result is visible, and embodiment 1-5 nano bone frame system significantly can increase its dissolubility (Fig. 1-3) compared with crude drug, wherein embodiment 1 optimum (Fig. 1).
Effect experiment in test example 2 body
Testing used is the female BAl BIc/C nude mice of 20g ± 2g.Method is as follows:
By MDA-MB-231 human breast cancer cell subcutaneous vaccination oxter on the left of nude mice, latter 5th day of inoculation, tumor volume grows to 150mm
3-200mm
3, be divided at random by nude mice 4 groups (often organizing 7), each group, by gastric infusion once a day, gives following 4 kinds:
1) normal saline
2) BAY 43-9006 crude drug, 40mg/kg
3) embodiment 1 nano bone frame system, is equivalent to the BAY 43-9006 of 40mg/kg
4) the blank nanometer skeleton of non-medicine carrying, is equivalent to 3) in carrier amount
First time administration started to measure tumor volume and Mouse Weight the same day, within every two days, measured once, until administration in 26 days terminates.
Tumor volume result is visible, and described in embodiment 1, nano bone frame system group tumor has no and rises appreciably, and inhibition is obviously better than other three groups (Fig. 4), and drug effect in its body with expection is described.And the gross tumor volume growth trend of blank nanometer skeleton group and normal saline group is basically identical and without obvious toxicity, again prove the safety of carrier material.
Above with general illustrating, detailed description of the invention and test to invention has been detailed description, modifications or improvements without departing from theon the basis of the spirit of the present invention, all belong to the scope of protection of present invention.
Claims (9)
1. one kind carries the nano bone frame system of insoluble drug, it is characterized by: comprise (1) one or more insoluble drugs, (2) nano bone frame material mesoporous silicon oxide, the polymer dispersed material HPMC that (3) optionally exist and (4) amphipathic nature material DSPE-PEG.
2. the nano bone frame system of according to claim 1 year insoluble drug, it is characterized in that: wherein, the quality of described insoluble drug and mesoporous silicon oxide is 1:1-5 than scope, and/or the quality of described insoluble drug and HPMC is 1:0-5 than scope, and/or the quality of described insoluble drug and DSPE-PEG is 1:1-5 than scope.
3. the nano bone frame system carrying insoluble drug according to any one of claim 1-2, the ratio of described insoluble drug, mesoporous silicon oxide, HPMC, DSPE-PEG is 1:3:0:3,1:3:1.5:1.5 or 1:3:3:3, is preferably 1:3:3:3.
4. the nano bone frame system carrying insoluble drug according to any one of claim 1-3, it is characterized in that described insoluble drug is selected from: one or more in yew alkanes, camptothecin, antibiotics antineoplastic agent, BAY 43-9006 are BAY 43-9006, and/or described DSPE-PEG is DSPE-PEG
2000.
5. the preparation method of carrying the nano bone frame system of insoluble drug described in any one of claim 1-4, it comprises the steps::
1) mesoporous silicon oxide is distributed in dichloromethane, under magnetic stirring, adds the insoluble drug being dissolved in organic solvent, obtain mixture 1.;
2) HPMC is scattered in dichloromethane, obtains mixture 2.;
1. and 2. 3) by mixture respectively simultaneously after ultrasonic 20-40min, under magnetic stirring, 2. mixture is added drop-wise to mixture 1. in and Keep agitation 24h, obtain mixture 3.;
4) 4. the organic solvent that reduction vaporization removing dichloromethane and insoluble drug are dissolved under the condition of 30-50 DEG C (preferably 40 DEG C), obtain mixture;
5), after DSPE-PEG being dissolved in dichloromethane, being joined and mixture revolving 4. is housed steams in bottle, ultrasonic 15min;
6) reduction vaporization under the condition of 30-50 DEG C (preferably 40 DEG C), collects solid, pulverizes and obtain the nano bone frame system carrying insoluble drug.
6. the preparation method of the nano bone frame system of according to claim 4 year insoluble drug, is characterized in that step 1) in the organic solvent that is dissolved in of insoluble drug be selected from methanol, ethanol and/or acetonitrile.
7. described in claim 1-4 any one carry insoluble drug nano bone frame system or according to any one of claim 5-6 the preparation-obtained nano bone frame system of preparation method preparing the application in antitumor drug.
8. comprise the pharmaceutical composition carrying the nano bone frame system of insoluble drug described in any one of claim 1-4.
9. pharmaceutical composition according to claim 8, described compositions is oral formulations.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108338971A (en) * | 2018-03-13 | 2018-07-31 | 苏州大学 | The application of the preparation method of administration nano-drug administration system based on native protein shale and administration nano-drug administration system based on native protein shale |
| CN108578712A (en) * | 2018-05-14 | 2018-09-28 | 杭州市肿瘤医院 | A kind of polymer-drug conjugate and preparation method thereof |
| CN115137817A (en) * | 2021-03-31 | 2022-10-04 | 临沂大学 | Preparation method and application of gold nanorod/platina-iron nano diagnosis and treatment agent |
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| WO2006088337A1 (en) * | 2005-02-21 | 2006-08-24 | Nanohybrid Co., Ltd. | A base forming drug-layered silicate hybrid containing basic polymer and its synthesis method |
| CN1842324A (en) * | 2003-09-05 | 2006-10-04 | Ss制药株式会社 | Pharmaceutical composition with improved solubility and fluidity |
| CN1927203A (en) * | 2005-09-09 | 2007-03-14 | 梁伟 | Nano micelle preparation of Catharanthus roseus alkaloids antineoplastic drugs with coating of phospholipid derived from polyethylene glycol |
| CN102657598A (en) * | 2012-05-09 | 2012-09-12 | 上海交通大学 | Porous inorganic material based oral preparation of secondary-dispersion insoluble drug and preparation method thereof |
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2015
- 2015-12-02 CN CN201510870096.1A patent/CN105343006B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1842324A (en) * | 2003-09-05 | 2006-10-04 | Ss制药株式会社 | Pharmaceutical composition with improved solubility and fluidity |
| WO2006088337A1 (en) * | 2005-02-21 | 2006-08-24 | Nanohybrid Co., Ltd. | A base forming drug-layered silicate hybrid containing basic polymer and its synthesis method |
| CN1927203A (en) * | 2005-09-09 | 2007-03-14 | 梁伟 | Nano micelle preparation of Catharanthus roseus alkaloids antineoplastic drugs with coating of phospholipid derived from polyethylene glycol |
| CN102657598A (en) * | 2012-05-09 | 2012-09-12 | 上海交通大学 | Porous inorganic material based oral preparation of secondary-dispersion insoluble drug and preparation method thereof |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108338971A (en) * | 2018-03-13 | 2018-07-31 | 苏州大学 | The application of the preparation method of administration nano-drug administration system based on native protein shale and administration nano-drug administration system based on native protein shale |
| CN108578712A (en) * | 2018-05-14 | 2018-09-28 | 杭州市肿瘤医院 | A kind of polymer-drug conjugate and preparation method thereof |
| CN108578712B (en) * | 2018-05-14 | 2021-08-24 | 宁波市杭州湾医院 | Polymer-drug conjugate and preparation method thereof |
| CN115137817A (en) * | 2021-03-31 | 2022-10-04 | 临沂大学 | Preparation method and application of gold nanorod/platina-iron nano diagnosis and treatment agent |
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| CN105343006B (en) | 2019-05-14 |
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