CN108619524A - A kind of poly (lactic acid) composition and preparation method thereof - Google Patents
A kind of poly (lactic acid) composition and preparation method thereof Download PDFInfo
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- CN108619524A CN108619524A CN201710155463.9A CN201710155463A CN108619524A CN 108619524 A CN108619524 A CN 108619524A CN 201710155463 A CN201710155463 A CN 201710155463A CN 108619524 A CN108619524 A CN 108619524A
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
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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
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
- A61K9/0024—Solid, semi-solid or solidifying implants, which are implanted or injected in body tissue
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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
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1617—Organic compounds, e.g. phospholipids, fats
- A61K9/1623—Sugars or sugar alcohols, e.g. lactose; Derivatives thereof; Homeopathic globules
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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
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1652—Polysaccharides, e.g. alginate, cellulose derivatives; Cyclodextrin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/14—Macromolecular materials
- A61L27/18—Macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/14—Macromolecular materials
- A61L27/20—Polysaccharides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/50—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/50—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
- A61L27/58—Materials at least partially resorbable by the body
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2400/00—Materials characterised by their function or physical properties
- A61L2400/06—Flowable or injectable implant compositions
Abstract
The invention discloses a kind of poly (lactic acid) compositions.The composition is made of polylactic acid, suspending agent, excipient, and polylactic acid is 20~50 parts by weight percentage, and suspending agent is 10~30 parts, and excipient is 20~50 parts.The present invention is put into 20~50min of crushing in airslide disintegrating mill after pre-processing 20~100min under 150 DEG C~100 DEG C environment, is added in the aqueous solution containing excipient and suspending agent and be dried in vacuo by the polylactic acid raw material of 10~15w of relative molecular weight.Feature is that surfactant is free of in composition, and preparation process is easy, can reach the purpose of high yield amplification, is suitble to industrialized production, and contain l-lactic acid and dextrorotation polylactic acid, reaches not only quick acting, but also the effect of long-acting maintenance.
Description
Technical field
The present invention relates to a kind of poly (lactic acid) compositions and preparation method thereof, it particularly relates to which a kind of modified technique is double
The composition and preparation method thereof for revolving polylactic acid injection implant, belongs to biomedicine technical field.
Background technology
Polylactic acid (polylactide, PLA) and its copolymer are a kind of macromolecule polymeric materials, have good biology
Compatibility and biodegradability, all products are nontoxic, vitals will not be caused to assemble.By U.S.'s food and medicine
Management board (FDA) approves the beautifying use of PLA preparations, and for improving the wrinkles such as decree line (laugh line), majority is freeze-dried powder
Injection is redissolved into suspension with sterile water for injection when use.On the one hand, existing product is mostly l-lactic acid product, people
Body absorbs slowly, works slow, is still polylactic acid preparation project urgently to be resolved hurrily.On the other hand, existing industrialization technology to equipment and
Personnel requirement is high, and preparation process is the problem of urgently optimization.
Microball preparation is emerging dosage form in recent years, and for novel form, there is no general production equipment, productions in the world
It is main bugbear at this stage that industry ability is low, and the present invention provides a kind of new industrialization polylactic acid microsphere preparations, drop significantly
Low technology difficulty, can be with effective solution industrialization problem.
Commercially available productIt is a kind of l-lactic acid particle filling of Sai Nuofei (Sanofi) company production and sales
Preparation, be originally approved for treatment patient HIV facial fat missing, after by FDA approval be used for beauty industry.The kind is
Polylactic acid is demonstrated by 96 weekly datas of clinic and fills the safety and effectiveness of preparation, but still is had the following disadvantages：
1) it works slow：Because it contains only l-lactic acid, absorb it is slow, therefore since the 8th week just obviously action.
2) complex process：Commercially available product is freeze-dried powder, and finished product of the present invention greatly reduces technique hardly possible without freeze-drying
It spends and takes, and then reduce cost, be suitble to industrialized production.
A kind of polylactic acid raw material Freezing smashing technology is reported in patent application CN104292476A.The invention with it is above-mentioned specially
Sharp method is entirely different, can get the particle of particle size range relatively narrow (40~100 microns) and crushes yield higher than 80%.But still it deposits
In following problem：1) technology carries out freezing pretreatment using refrigerator to raw material, and when quick-frozen effect is bad, material is easily tied
Block, and cooling time is long, energy consumption is high, is not easy amplification production；2) invention after being pulverized, still needs to sieving screening, can substantially reduce
Yield improves cost.
For defect existing for polylactic acid preparation in the prior art, it is necessary to which above-mentioned ask can be overcome by designing and developing one kind
The bispin polylactic acid preparation of topic is suitable for injection implant face filling, and without carrying medicine, and specific size distribution is uniform, has
Better clinical effectiveness.
Invention content
The purpose of the present invention is to provide a kind of bispin poly (lactic acid) compositions for skin filling to be applicable in without carrying medicine
In injection implant formula face filling.
It is another object of the present invention to provide a kind of bispin polylactic acid preparations for skin filling, without carrying medicine,
Suitable for injection implant formula face filling.
It is another object of the present invention to provide a kind of preparation methods preparing above-mentioned preparation.
To achieve the goals above, a kind of poly (lactic acid) composition using novel crushing technology according to the present invention, by
Polylactic acid, suspending agent, excipient composition, by weight percentage polylactic acid are 20~50 parts, and suspending agent is 10~30 parts, excipient
It is 20~50 parts.
Heretofore described poly (lactic acid) composition, it is characterised in that the polylactic acid relative molecular weight is 10~15W, official
It can roll into a ball as aldehyde radical, inherent viscosity is 1.7~2.3dL/g.
Heretofore described poly (lactic acid) composition, it is characterised in that the excipient is in lactose, sucrose and mannitol
It is one or more
Heretofore described poly (lactic acid) composition, it is characterised in that the suspending agent is sodium carboxymethylcellulose or alginic acid
It is one or more in sodium.
A kind of heretofore described polylactic acid preparation, average grain diameter are 15~70 microns, contain above-mentioned polylactic acid group
Close object.
The polylactic acid preparation is preferably vacuum dried preparation.
The preparation method of polylactic acid preparation of the present invention includes the following steps：
1) 20~50 parts of polylactic acid raw materials are pre-processed with refrigerant；
2) polylactic acid after freezing is put into airslide disintegrating mill to be crushed under a certain pressure；
3) the polylactic acid particle after crushing is suspended in water-soluble containing 20~50 parts of excipient and 10~30 parts of suspending agents
In liquid；
4) 800rpm is dried in vacuo after stirring 10min.
In the present invention, the preparation method, step 1) selects refrigeration agent material for liquid nitrogen in low-temperature treatment, and temperature
Ranging from -150 DEG C~-100 DEG C, 20~100min of low-temperature treatment.
In the present invention, the preparation method need to be through air-flow crushing through cryogenically treated polylactic acid particle in step 2)
Machine crushes 20~50min under 0.4bar~1.0bar pressure.
Advantage of the present invention is as follows：
Technique is excellent：1) compared with other technologies, the present invention is simple for process without being lyophilized, and is easy to industrialized production；2) raw material
It is crushed using ultralow temperature, it is quick-frozen rapid, it is prevented from caking；3) do not have to screening after the completion of crushing, it is easy to operate, at low cost.
Curative effect：Existing polylactic acid formulation products are mostly l-lactic acid product, are worked slow.The present invention produces for bispin polylactic acid
Product, wherein dextrorotation polylactic acid absorb soon, can comparatively fast stimulate subcutaneous fibrotic cell to generate collagen, play true filling effect,
Reach quick acting, but because its degradation speed is fast, the longer l-lactic acid of degradation time need to be coordinated just to can reach together quickly
It works and the long feature of drug effect.The present invention fine can be obtained simultaneous by the ratio controlled between l-lactic acid and dextrorotation polylactic acid
Hold rapid-action and continues long two big characteristics.
The present invention is described further with reference to embodiment, but the present invention is not limited in embodiment, it is all according to this
This field equivalent replacement that disclosure of the invention content is done, all belongs to the scope of protection of the present invention.
Description of the drawings
Fig. 1 and Fig. 2 is the electron microscope of polylactic acid microsphere prepared by embodiment 4；
Fig. 3 is embodiment and commercially available product grain size comparison diagram；
Embodiment
Preparation method
1) polylactic acid raw material of 1.7~2.3dL/g of inherent viscosity is pre-processed with refrigerant；
2) polylactic acid after freezing is put into airslide disintegrating mill to be crushed under a certain pressure；
3) the polylactic acid particle after crushing is suspended in the aqueous solution containing excipient and suspending agent；
4) 800rpm is dried in vacuo after stirring 10min.
Prescription：
1 each embodiment formulation and technology contrast table of table
Good effect is further illustrated the present invention below by way of experimental data：
1, yield is tested：
Method：With polylactic acid raw material m0On the basis of, microball preparation is prepared by the prescription and preparation method of above-described embodiment, is surveyed
The polylactic acid weight m in preparation is obtained, yield W is calculated according to the following formula：
W=m ÷ m0X 100%.
Each embodiment the results are shown in Table 2
2, particle size range is tested
Method：Above-described embodiment and commercially available product are separately added into water for injection and are prepared into suspension, using Malvern
MS3000 laser granulometries are measured under same test condition within the scope of same obscurity.It falls into a trap from test result
The ratio between 35~60 microns is calculated, reflects its specified particle diameter yield with this ratio, ratio is higher, and yield is higher.Test knot
Fruit is shown in Table 2
Table 2：Embodiment experimental result
| Embodiment 1 | Embodiment 2 | Embodiment 3 | Embodiment 4 | Commercially available product | |
| Yield (%) | 90.35 | 92.90 | 88.30 | 90.50 | - |
| Specified particle diameter ratio (35-60) (%) | 41.02 | 38.91 | 37.56 | 40.12 | 35.44 |
Conclusion：
According to shown in table 2 as a result, can obtain to draw a conclusion：
1) yield：When each component ratio is in the scope of the present invention, yield can reach 85% or more, further prove
The high production capacity of present invention process；
2) particle diameter distribution：
A) as shown in Table 2, with the continuous increase of cryogenic temperature and time, polylactic acid raw material brittleness is bigger, grain after crushing
Diameter is less than normal；With the increase for crushing pressure and time, grain size is less than normal after crushing；
B) by the way that experimental results demonstrate the ratio between 35~60 microns of specified particle diameter range reaches 30%~50%
When, this preparation has better clinical effectiveness, and as shown in Table 2, grain size is by each component ratio and technological parameter joint effect, in this hair
In the bright optimized scope obtained, the special ratios within the scope of specified particle diameter are can reach, there is clinical advantage.
3, external degradation test method
This test is tested according to the professional standard that number is YY/T 0474-2004.
1) preparation of buffer solution：Buffer solution used is phosphate buffer, the di(2-ethylhexyl)phosphate configured with sterile redistilled water
Hydrogen potassium and disodium hydrogen phosphate, the salt for being used to prepare the buffer solution should be analytically pure and dry to constant
A) 1/15mol/L potassium dihydrogen phosphates：9.078g potassium dihydrogen phosphates are dissolved in every liter of water；
B) 1/15mol/L disodium hydrogen phosphates：11.876g phosphate dihydrate disodium hydrogens are dissolved in every liter of water
The buffer solution is mixed by 18.2% solution a) and 81.8% solution b) (volume fraction).Difference should be measured weekly
PH value in container carries out pH adjustings when needing with the NaOH solution of 0.1mol/L, make the pH value of the buffer solution remain 7.4 ±
0.2；
2) sample preparation：It takes above-described embodiment 4 and commercially available product each 6 (500mg/ branch) to be respectively placed in beaker, pours into note
Penetrating ultrasound 5min after being redissolved with water makes it fully dissolve, centrifugal filtration, then is dried in vacuo to screening, weighs initial weight
m0, it is respectively placed in seal glass conical flask, sample, the wherein volume (ml) of buffer solution and examination is completely covered with 10ml buffer solutions
It tests the ratio between sample quality (g) and is more than 30:1, the real time degrade (each 3) maintain sample in (37 ± 1) DEG C with water bath with thermostatic control
Physiological temp, accelerated degradation (each 3) maintain sample in the physiological temp of (70 ± 1) DEG C with water bath with thermostatic control.
3) microballoon and solution are detached：Vacuum filtration makes polylactic acid microsphere be detached with degraded solutions, and analysis water washing three is used in combination
It is secondary, it collects filter residue and is used for inherent viscosity, mass loss and droplet measurement, collect filtrate and detect use for lactic acid content.
4) catabolite measures：Using ion chromatograph detecting step 3) content of lactic acid anion (surveys three bottles in filtrate
Filtrate), chromatographic column be Dai An companies of U.S. AG22 columns, leacheate be NaHCO3 solution (6.0mmol/L), flow velocity 1ml/min,
Sampling volume be 10 μ L, 30 DEG C of column temperature, 35 DEG C of Chi Wen, electric conductivity detector detection, measure initial lactic acid anion-content a0, then
Lactic acid anion-content a is measured in the set time, degradation percentage W is calculated according to following equation：
W=(a/a0- 1) x100%
5) characteristic viscosity determining：Filter residue isolated in step 3) is placed in 40 DEG C and is dried under vacuum to constant weight, after be dissolved in
Chloroform is configured to a concentration of 0.1% test sample, and by GB/T1632 (ISO1628-1), with micro determination of ubbelohde viscometer, it is special
Property viscosity (survey three bottles of filter residues).
Test result is shown in Table 3~6.
3 external real time of table degradation percent data contrast table
4 external accelerated degradation percent data contrast table of table
The front and back physicochemical property contrast table of 5 real time of table degradation
Physicochemical property contrast table before and after 6 accelerated degradation of table
Because the degradation of polylactic acid is a complicated process, high polymer is first decomposed into single-stranded, then is decomposed into lactic acid monomer, therefore
The present invention reflects the degradation rate of polylactic acid with the quantity of lactic acid anion to a certain degree.
It can be seen that by table 3~4, because the present invention is added to dextrorotation polylactic acid, degradation is very fast, so early period, degradation can be faster than
Commercially available product, but the later stage slow down gradually again, can reach quick acting again can maintain the effect of permanent drug effect；It can be seen that by table 5~6,
The continuous degradation of polylactic acid at any time, dry mass reduce, and molecular weight reduces, and inherent viscosity and grain size reduce therewith.Because of polylactic acid
Degradation can be divided mainly into the water suction of high polymer, the hydrolytic cleavage of ester bond, soluble oligomer three processes of diffusion dissolution,
In water absorption course, since the hydrolysis of the diffusion ratio ester bond of water wants much faster, the hydrolysis of ester bond is uniform in the incipient stage
, with the continuation of degradation, the autocatalysis of end carboxyl is more apparent, can further increase degradation rate.
Though this data is in-vitro measurements, can side reflect its material result, and then reflect interior curative effect.
Claims (10)
1. a kind of poly (lactic acid) composition is made of polylactic acid, suspending agent, excipient, it is characterized in that：Polylactic acid by weight percentage
It it is 20~50 parts, suspending agent is 10~30 parts, and excipient is 20~50 parts.
2. poly (lactic acid) composition according to claim 1, it is characterised in that the polylactic acid relative molecular weight be 10~
15W, containing D- polylactic acid and l-polylactic acid, functional group is aldehyde radical, and inherent viscosity is 1.7~2.3dL/g.
3. poly (lactic acid) composition according to claim 2, which is characterized in that the ratio between contained l-polylactic acid and D- polylactic acid are
L:D=4:1~1:4.
4. poly (lactic acid) composition according to claim 1, it is characterised in that the excipient is lactose, sucrose and mannitol
In it is one or more.
5. poly (lactic acid) composition according to claim 1, it is characterised in that the suspending agent be sodium carboxymethylcellulose and
It is one or more in sodium alginate.
6. a kind of bispin polylactic acid preparation, it is characterised in that：Contain the polylactic acid combination described in any one of claim 1 to 5
Object forms, and average grain diameter is 15~70 microns.
7. bispin polylactic acid preparation according to claim 6, which is characterized in that finished product is a kind of vacuum dried system
Agent.
8. the bispin poly (lactic acid) composition preparation method described in a kind of any one of claim 6~7 comprising following step
Suddenly：
1) 20~50 parts of polylactic acid raw materials are pre-processed with refrigerant；
2) polylactic acid after freezing is put into airslide disintegrating mill to be crushed under a certain pressure；
3) the polylactic acid particle after crushing is suspended in the aqueous solution containing 20~50 parts of excipient and 10~30 parts of suspending agents；
4) 800rpm is dried in vacuo after stirring 10min.
9. preparation method according to claim 8 selects refrigeration agent material for liquid nitrogen in low-temperature treatment, and temperature range
It is -150 DEG C~-100 DEG C, 20~100min of low-temperature treatment.
10. preparation method according to claim 8 need to exist through cryogenically treated polylactic acid particle through airslide disintegrating mill
20~50min is crushed under 0.4bar~1.0bar pressure.
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110066500A (en) * | 2019-04-11 | 2019-07-30 | 成都迪康中科生物医学材料有限公司 | Degradable injection class polylactic acid filler of one kind and preparation method thereof |
| CN110339397A (en) * | 2019-07-11 | 2019-10-18 | 山东省药学科学院 | A kind of injectable dermal filler and its preparation method and application without suspending agent |
| CN110721338A (en) * | 2019-10-29 | 2020-01-24 | 普丽妍（南京）医疗科技有限公司 | Preparation method of injectable L-polylactic acid particles |
| CN110721339A (en) * | 2019-10-29 | 2020-01-24 | 普丽妍（南京）医疗科技有限公司 | Rapid preparation method of injectable L-polylactic acid particles |
| CN113117142A (en) * | 2020-01-14 | 2021-07-16 | 北京四环制药有限公司 | Biodegradable injection filler, preparation method and application thereof |
| CN113546539A (en) * | 2020-04-24 | 2021-10-26 | 透策生技股份有限公司 | Treatment method for accelerating dispersion of injection filler by using pressurization means |
| CN115887760A (en) * | 2022-11-21 | 2023-04-04 | 娜罗曼苏(杭州)医疗生物科技有限公司 | Preparation process of L-polylactic acid for injection |
-
2017
- 2017-03-18 CN CN201710155463.9A patent/CN108619524A/en not_active Withdrawn
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110066500A (en) * | 2019-04-11 | 2019-07-30 | 成都迪康中科生物医学材料有限公司 | Degradable injection class polylactic acid filler of one kind and preparation method thereof |
| CN110066500B (en) * | 2019-04-11 | 2021-04-20 | 成都迪康中科生物医学材料有限公司 | Degradable injection polylactic acid filler and preparation method thereof |
| CN110339397A (en) * | 2019-07-11 | 2019-10-18 | 山东省药学科学院 | A kind of injectable dermal filler and its preparation method and application without suspending agent |
| CN110721338A (en) * | 2019-10-29 | 2020-01-24 | 普丽妍（南京）医疗科技有限公司 | Preparation method of injectable L-polylactic acid particles |
| CN110721339A (en) * | 2019-10-29 | 2020-01-24 | 普丽妍（南京）医疗科技有限公司 | Rapid preparation method of injectable L-polylactic acid particles |
| CN110721338B (en) * | 2019-10-29 | 2021-12-14 | 普丽妍（南京）医疗科技有限公司 | Preparation method of injectable L-polylactic acid particles |
| CN113117142A (en) * | 2020-01-14 | 2021-07-16 | 北京四环制药有限公司 | Biodegradable injection filler, preparation method and application thereof |
| CN113117142B (en) * | 2020-01-14 | 2023-09-19 | 渼颜空间(河北)生物科技有限公司 | Biodegradable injection filler, preparation method and application thereof |
| CN113546539A (en) * | 2020-04-24 | 2021-10-26 | 透策生技股份有限公司 | Treatment method for accelerating dispersion of injection filler by using pressurization means |
| CN115887760A (en) * | 2022-11-21 | 2023-04-04 | 娜罗曼苏(杭州)医疗生物科技有限公司 | Preparation process of L-polylactic acid for injection |
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