KR101096679B1 - Composite particles comprising cationic polymers and anionic polymers prepared by electro-spray drying - Google Patents

Composite particles comprising cationic polymers and anionic polymers prepared by electro-spray drying Download PDF

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KR101096679B1
KR101096679B1 KR1020090052964A KR20090052964A KR101096679B1 KR 101096679 B1 KR101096679 B1 KR 101096679B1 KR 1020090052964 A KR1020090052964 A KR 1020090052964A KR 20090052964 A KR20090052964 A KR 20090052964A KR 101096679 B1 KR101096679 B1 KR 101096679B1
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이종휘
박세현
호환기
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중앙대학교 산학협력단
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The present invention relates to a composite particle of the cationic polymer and anionic polymer prepared by electrospray drying, more specifically, the cationic polymer and the anionic polymer are present in an uncrosslinked state, but can be rapidly crosslinked by water. It is a core-shell structured microcomposite particle, which is manufactured through electrospray drying, which has a small particle size and an electric charge on the surface of the particle to reduce aggregation between particles, and form a capsule structure to form an active ingredient therein. It is supported by being bonded to the outside, and its sustained release is possible.
Electrospray drying, microcomposite particles, cationic polymers, anionic polymers, active ingredients

Description

Composite particles comprising cationic polymers and anionic polymers prepared by electro-spray drying}

The present invention relates to a composite particle of the cationic polymer and anionic polymer prepared by electrospray drying, more specifically, the cationic polymer and the anionic polymer are present in an uncrosslinked state, but can be rapidly crosslinked by water. It is a core-shell structured microcomposite particle, which is manufactured through electrospray drying, which has a small particle size and an electric charge on the surface of the particle to reduce aggregation between particles, and form a capsule structure to form an active ingredient therein. It is supported by being bonded to the outside, and its sustained release is possible.

Spray drying is a method that has already been used in many pharmaceutical formulations by continuously spraying liquid samples and spraying them to form finely dispersed droplets and instant drying with hot air (Broadhead et al, Drug Dev. Ind. Pharm , 18 (11 & 12): 1169 (1992). The spray drying method has the advantage of making powder into particles of a size suitable for transporting medicines to the airways or lungs through inhalation, and saves money and time at the production site due to low energy consumption. In particular, when preparing a spray-dried composition for use in the respirator, it is preferable to formulate in powder form of 5㎛ or less. At this time, the size distribution, shape, and water content of the powder are important factors in the therapeutic efficacy (Hickey et al, Pharm. Tech ., 18:58 (1998)). In determining the physical properties of the powder, the instrument conditions such as the temperature of the hot air, the feed rate of the drug solution, and the spray pressure, and the concentration of the drug solution are important factors.

Electrospray is a method of preparing microparticles by injecting a polymer solution having a certain degree of electrical conductivity and viscosity into a capillary and applying an electrostatic force to facilitate the manufacture of the device. The generated particles are not only able to have a monodispersion distribution but are also useful for preparing particles of various sizes, and thus, recent researches are being applied to the production of drug-containing particles in the field of drug delivery (Xie et al, Biomaterials, 27: 3321 (2006).

Hydrogel does not dissolve in water but has swelling properties and is a cross-linked three-dimensional network of hydrophilic polymers. Hydrogel materials which may be biodegradable may be used as drug carriers and the like. It is known that a cationic polymer material without a crosslinking agent is mixed with an anionic polymer material to form a crosslinked hydrogel, and it is possible to prepare particles having sustained release by supporting drugs and active ingredients (Sakiyama et al, J.). Applied Polymer Science , 73: 2227 (1999). However, such crosslinking has a disadvantage in that the time is slow and inhomogeneously proceeds in a simple mixture. In addition, the drug must be supported before crosslinking, so that sufficient drug can be supported. In this case, the crosslinking and the shape formation of the particle and the drug support must be performed simultaneously, causing many problems. The crosslinking agent may cause decomposition of the drug, and the like, and the particle shape size may vary depending on the crosslinking reaction, the properties of the drug, and the like, and there may be a limit in increasing the amount of the drug.

Conventional spray drying is used in the powder manufacturing process and food powder manufacturing process of the pharmaceutical industry. Spray drying in the manufacture of drug powders has the advantage of producing powders that are suitable for transporting drugs in drug delivery by inhalation, or drug delivery using particulate sieves, with low energy consumption, and saves time and money in production. have. However, particle manufacturing through spray drying has problems of uneven distribution of particle shape and uneven distribution of particle size. On the other hand, the electrospray particle production method can produce particles with uniform particle size, but electrospray particle production has a problem of low productivity.

Hydrogels are used for drug delivery and various applications. Sakiyama et al. ( J. Applied Polymer Science , 73: 2227 (1999)) introduced a method for preparing a hydrogel using chitosan, a cationic polymer, and dextran sulfate, an anionic polymer, without a crosslinking agent. After stirring the two polymer solutions by a simple mixing method, a salt was added, heat was added, and centrifugation was performed to lower the temperature again. It takes 24 hours to crosslink. This method cannot produce hydrogel particles of a certain size and shape, cannot carry drugs and active ingredients, and is difficult to use commercially for a long time and many process steps. Sezer ( Journal of Microencapsulation , 23 (5): 513 (2005)) prepared hydrogel particles using chitosan, a cationic polymer, and fucoidan, an anionic polymer. After dissolving the drug with fucoidan and dropping it dropwise dropwise to a solution containing chitosan, the obtained particles were freeze-dried to obtain particles using sieve. This method can support the drug and the active ingredient, but the drug naturally diffuses as it enters the chitosan solution, so that effective loading cannot be expected, and it is difficult to control the particle size which affects future release. In addition, the time required to prepare the particles is difficult to use commercially.

In this regard, there is a need for a method that enables effective drug and active ingredient loading, uniformly sized particles production, and short production times.

SUMMARY OF THE INVENTION An object of the present invention is to provide a composite particle capable of effectively carrying a pharmaceutically active ingredient and sustained release thereof while the cationic polymer and the anionic polymer are present in an uncrosslinked state through electrospray drying, and a method for preparing the same. .

Another object of the present invention is to provide a use as a drug carrier of the composite particles of the excellent physical properties.

In order to achieve the above object, the present invention is a composite particle comprising a cationic polymer and an anionic polymer,

The polymers provide a composite particle comprising a core-shell structure which is not crosslinked by electrospray drying.

The invention also

Preparing a crosslinkable cationic polymer or anionic polymer solution;

Electrospraying the polymer solution through two co-axial nozzles, respectively; And

It provides a method for producing a multiparticulate of the present invention comprising the step of obtaining a multiparticulate.

The present invention also provides a composite particle of the present invention; And

Provided is a drug delivery agent comprising a pharmaceutically active ingredient.

The present invention is a composite particle having a core-shell structure in a state in which the cationic polymer and the anionic polymer are not cross-linked, and can be reduced by agglomeration of particles by manufacturing through electrospray drying, and the particle size of a smaller and more uniform shape can be reduced. It is easily crosslinked by water to carry the pharmaceutically active ingredient therein or in a combined form, so that the sustained release is effective.

EMBODIMENT OF THE INVENTION Hereinafter, the structure of this invention is demonstrated concretely.

The present invention is a composite particle comprising a cationic polymer and an anionic polymer,

The polymers are related to the composite particles, which form a core-shell structure that is not crosslinked by electrospray drying.

The composite particles of the present invention are prepared in a state in which the crosslinkable cationic polymer and anionic polymer maintain the state before crosslinking, and in forming the particles through spray drying, an electric field is formed by applying a voltage to the surface of the liquid by an electric field. This can be achieved by breaking the balance between the electrostatic force, the force that pulls the liquid, and the surface tension of the liquid, causing the surface of the liquid to break and generate a large number of very fine spray particles (microdroplets) from the liquid.

In preparing the composite particles of the present invention in which redispersion is easily suppressed through the electrospray drying, cationic polymers or anionic polymers may be sprayed through two co-axial nozzles, respectively. Thus, the sprayed droplets can maintain the encapsulation structure. The composite particles produced by electrospray drying and co-axial nozzles have reduced cohesion with each other due to charge repulsion.

The encapsulation structure of the droplets may represent a core-shell structure in which the anionic polymer surrounds the cationic polymer or the cationic polymer surrounds the anionic polymer. More preferably, when the cationic polymer is located on the outside to support the active material therein, the stability of the active material can be ensured.

The composite particles of the present invention may be prepared before crosslinking, but crosslinking may occur without crosslinking agents when crosslinkable polymers are exposed to water.

The crosslinkable cationic polymer may be a compound having an amine group (-NH 2 ) having a cation upon dissociation. More specifically, chitosan, poly (allyamine) hydrochloride, polyacrylonitrile, poly (trans-4-hydroxy-proline ester (poly (trans-4) hydroxy-proline esters), polylysine, poly (lactide-co-lysine), poly serine ester, or poly (α- (4 -Aminobutyl) -glycolic acid) (poly (α- (4-aminobutyl) -glycolic acid)) or the like can be used alone or in combination of two or more thereof.

The crosslinkable anionic polymer is a compound having an alcohol group (-OH), a carboxyl group (-COOH), a sulfur related group (-O 3 SOH, -SH), or a phosphoric acid group (-O 3 POH) having an anion upon dissociation Can be. More specifically, acacia, alginate, carrageenan, chondroitin sulfate, carboxylmethylcellulose, dextran sulfate, fucoidan, gellan gum ( gellan gum, heparin, hyaluronic acid, pectin, xanthane, xylan, polystyrene sulfonate, collagen, poly acrylic acid acid), polyphosphoric acid, polyphosphate, poly (lactide), or poly (lactide-co-glycolic acid) ) May be used alone or in combination of two or more.

The cationic polymer and the anionic polymer may be included in a weight ratio of 1:10 to 10: 1 according to the properties of the substituents substituted in each material so as to support the drug, the active ingredient and the like.

In addition, the composite particles of the present invention have a smaller particle size than those produced through electrospray drying and spray drying. More specifically, the particle size may be 2-10 μm. In addition, the surface of the particles can be charged to reduce the aggregation between the particles.

In addition, the multiparticulate of the present invention may further include a pharmaceutically active ingredient enclosed or mixed therein.

The pharmaceutically active ingredient may be sprayed through a co-axial nozzle with a cationic polymer or an anionic polymer in the preparation of the multiparticulate of the present invention and encapsulated inside the multiparticulate, or mixed with the outside of the multiparticulate.

The invention also

Preparing a crosslinkable cationic polymer or anionic polymer solution;

Electrospraying the polymer solution through two co-axial nozzles, respectively; And

It relates to a method for producing a multiparticulate of the present invention comprising the step of obtaining a multiparticulate.

The method for producing a composite particle of the present invention relates to the preparation of a composite particle in which the crosslinkable cationic polymer and anionic polymer are present in the form of a core-shell structure before crosslinking through electrospray drying, It demonstrates concretely.

The first step is to prepare a crosslinkable cationic polymer solution and anionic polymer solution for spraying through a nozzle.

The type of the polymer solution is as described above, and the cationic polymer and the anionic polymer may be filled in the nozzle at a weight ratio of 1:10 to 10: 1 depending on the characteristics.

In addition, the cationic polymer or anionic polymer solution may further include a pharmaceutically active ingredient.

The pharmaceutically active ingredient may be enclosed in the core (core) of the composite particles prepared by electrospray drying or mixed in the shell part depending on which polymer solution is included.

The second step is the electrospray drying of the cationic polymer solution or the anionic polymer solution to two co-axial nozzles.

The nozzle has two inner shafts and an outer shaft so that the composite particles having a core-shell structure can be prepared when the polymer solution is sprayed.

The cationic polymer or the anionic polymer may be filled and sprayed into the outer shaft or the inner shaft nozzle, respectively, according to the properties of the material to form the core-shell structure of the composite particles of the present invention.

In addition, in order to enclose the pharmaceutically active ingredient in consideration of the sustained release of the pharmaceutically active ingredient contained in the anionic polymer solution and sprayed, to prepare in a mixed form to the outside the active in the cationic polymer solution It is advisable to spray, including the components.

The conditions of the electrospray drying to prepare the composite particles of the present invention is a temperature of 40 to 150 ℃, liquid rate of 0.25 to 70 mL / min, air flow of 1.5 to 110 L / min, voltage is 0.5 to 10 kV Can be.

In addition, a grid may be installed under the nozzle so that the electric field is more affected by the solution at the end of the nozzle during electrospray.

The third step is to obtain a multi-particle, the droplets sprayed through the nozzle is transferred to the vacuum pump of the spray drying apparatus, it can be obtained in a multi-particle state through a quick drying process.

The electrospray-dried particles show a method in which the particle size decreases as a high voltage is applied. Preferably, the particle size may be between 2 and 10 μm.

In addition, the composite particles of the present invention may react with water to cause crosslinking. The crosslinking reaction is preferably performed at 20 to 50 ° C. for 30 minutes to 12 hours, but is not particularly limited thereto.

Compared with the composite particles through spray drying, the composite particles of the present invention have a faster crosslinking time, obtain various crosslinking degrees, and control the release of the pharmaceutical active ingredient according to the crosslinking degree.

The present invention also provides a composite particle of the present invention; And

It relates to a drug carrier comprising a pharmaceutically active ingredient.

In the present invention, the 'pharmaceutical active ingredient' includes all biological and chemical substances used for the prevention, treatment, alleviation or alleviation of a disease, and substances that assist the pharmacological effects of other drugs are also included in the 'pharmaceutical' of the present invention. Pharmaceutically active ingredient. For example, anticancer agents, anti-inflammatory agents, antibacterial agents, antiviral agents, hormones, antioxidants and the like can be used as the 'pharmaceutical active ingredient' of the present invention.

In preparing the drug delivery system using the multiparticulate of the present invention, an additive may be used for controlling the drug release rate. The additives used may be in the form of micro or nano-sized small particles, or in the form of liquids or gels. The additive may be included in the form of the composite particles are mixed in the core constituting the core of the composite particles and encapsulated in the core through the co-axial nozzle, or mixed in the shell constituent components mixed in the shell through the co-axial nozzle .

In addition to the aforementioned components, it may also include conventional additives known in the art such as excipients, stabilizers, pH adjusters, antioxidants, preservatives, binders or disintegrants and the like. In this case, the carrier may further include other additives, solvents, and the like known in the art.

In addition, the drug carrier may be formulated in the form of oral or parenteral preparations, and may be prepared by intravenous, intramuscular or subcutaneous injection.

Hereinafter, the present invention will be described in more detail through examples according to the present invention and comparative examples not according to the present invention, but the scope of the present invention is not limited to the examples given below.

Production Example 1 Electric Spray Drying Device

The electrospray dryer uses the same apparatus except the spray dryer and the nozzle portion. The nozzle portion is modified to include a passage through which two or more solutions can flow and an apparatus for applying electricity to the nozzle. The nozzle part is insulated to prevent damage to the machine due to electric leakage of the existing spraying device, and a SUS ring serving as a grid is installed in the spray passage opposite the nozzle to apply voltage. . Instead of a nozzle with one solution channel, the two nozzles were converted to co-axial coaxial axes (FIG. 1).

Preparation Example 2 Preparation of Composite Particles

Electrospray drying with varying voltage was performed to investigate the difference between spray drying and electrospray drying. 9 parts by weight of polylysine was used for the inner shaft of the co-axial nozzle used for electrospray, and 1 part by weight of polyacrylic acid was used for the outer shaft of the nozzle. Spray drying conditions were injected at a temperature of 60 ℃ liquid rate of 0.5 mL / min polylysine and 0.5 mL / min polyacrylic acid, respectively, and the air flow was 473 L / min. Spray drying was performed by applying high voltage, and grid was used for stainless steel (SUS) ring. The particle size and distribution were analyzed using a particle size analyzer (Horiba, Japan).

Figure 112009036062101-pat00001

As shown in Table 1, the higher the voltage was applied, the smaller the particle size was. The particle size in electrospray drying was reduced than in the spray drying without high voltage, and it appears that fine droplets are generated by the influence of the electric field and smaller particles appear during the rapid drying process. Reducing agglomeration between particles is also an important cause of the reduction in particle size, which is a characteristic of this manufacturing method.

Example 1 Composite Particles of Chitosan / Fucoidan Prepared by Electrospray Drying

Spray drying conditions were the temperature of 60 ℃, flow meter spraying air 601 L / min. Chitosan was used as the cationic polymer and fucoidan was used as the anionic polymer. One part by weight of chitosan and one part by weight of fucoidan were used for the inner shaft of the co-axial nozzle. The liquid flow of chitosan solution was 0.82 mL / min and the liquid flow of fucoidan solution was injected at 0.27 mL / min. The spray drying was performed by applying a voltage of 2 kV, and the grid used SUS ring.

Under the same conditions as the co-axial spray drying, 1 part by weight of chitosan and fucoidan were obtained by electrospraying and the composite particles of chitosan and fucoidan obtained by using a co-axial nozzle were analyzed by scanning electron microscopy (SEM) (FIG. 2). ).

As shown in FIG. 2, it can be seen that the surface of the fucoidan particles is smoother than the chitosan particles. In the case of the composite particles, the surface of the fucoidan particles does not exist and the size of the fine particles does not crosslink, but the two materials are fine. It can be seen that the mixed state. This is a condition that can be quickly crosslinked by moisture, it can be seen that different from the simple mixed powder.

Energy dispersive X-ray (EDX) analysis of composite particles electrosprayed with a co-axial nozzle confirmed the sulfur (S) component present in the fucoidan to confirm that the fucoidan was encapsulated inside the external chitosan material. In addition, EDX results of the composite particles prepared by fucoidan, chitosan particles and electrospray drying using a co-axial nozzle prepared under the same conditions are shown in FIG.

As shown in FIG. 3, the EDX analysis result indicates that the composite particles contain S containing fucoidan in the chitosan-containing particles, and have a core-shell structure. Therefore, the fucoidan-chitosan composite particles having such a core-shell structure can be easily developed into a crosslinked state by moisture, and when the internal active material is used by placing a substance such as chitosan, which has less influence on water, than the fucoidan. It can contribute greatly to the stability of the active substance.

Example 2 Crosslinking of Chitosan / Fucoidan Composite Particles Prepared by Electrospray Drying

Drying conditions of the electrospray was 60 ℃, flow meter spraying air 601 L / min. Chitosan was used as the cationic polymer and fucoidan was used as the anionic polymer. One part by weight of chitosan and one part by weight of fucoidan were used for the outer axis of the co-axial shaft. The liquid flow of chitosan on the outer axis and fucoidan on the inner axis was injected at 0.82 mL / min to obtain composite particles. The particles were obtained.

In addition, the liquid flow of chitosan, which is an external axis, was spray-dried by adding 0.82 mL / min and 0.5 part by weight of an ALA (alpha lipoic acid) salt form as a model drug to 1 part of fucoidan.

Three kinds of the composite particles thus prepared were added in 0.07 g portions to 10 mL vials, and 0.9 mL of distilled water was added to each vial. The vial was stored for 30 minutes in a 50 ° C oven. The swelling ratio was measured by equilibrium swelling by soaking the cross-linked hydrogel in 7 mL of pH 4, 7, 9 solution for 24 hours. Take out the hydrogel and remove the surface moisture with an air spray to measure the weight, dry the hydrogel in a vacuum oven and then weigh.

As a result, the crosslinking of the composite particles of the present invention (crosslinking time <30 min) occurred more than twice as fast as the simple mixed powder (crosslinking time ˜1 hr).

In addition, the composite particles not only have a fast crosslinking time, but also obtain various crosslinking degrees, and it can be seen that the release of the active ingredient can be controlled according to the crosslinking degree. This fact could be confirmed through the swelling ratio, which is inversely proportional to the degree of crosslinking and proportional to the releaseability (FIG. 4).

1 shows an electrospray dryer of Preparation Example 1 according to the present invention.

Figure 2 shows the results of analyzing the cross-linking state of the composite particles of the cationic polymer chitosan and the anionic polymer fucoidan of Example 1 according to the present invention by scanning electron microscopy (SEM).

Figure 3 shows through the energy dispersive X-ray (EDX) analysis that the encapsulation of particles during the electrospray drying of Example 1 according to the present invention.

Figure 4 shows the swelling ratio of the particles obtained by spray drying and electrospray drying of Example 2 according to the present invention.

Claims (16)

  1. In the composite particles comprising a cationic polymer and an anionic polymer,
    The polymers form a core-shell structure by an electrospray drying method, and the composite particles are crosslinked by reacting with water.
  2. delete
  3. The method of claim 1,
    Cationic polymer is a composite particle which is a compound having an amine group.
  4. The method of claim 3,
    Compounds having amine groups include chitosan, poly (allyamine) hydrochloride, polyacrylonitrile, and poly (trans-4-hydroxy-proline esters (poly (trans-4) -hydroxy-proline ester), polylysine, poly (lactide-co-lysine), poly serine ester and poly (α- (4 -Aminobutyl) -glycolic acid) (poly (α- (4-aminobutyl) -glycolic acid)) at least one composite particle selected from the group consisting of.
  5. The method of claim 1,
    Anionic polymer is a composite particle which is a compound having a functional group of -OH, -COOH, -O 3 SOH, -SH, or -O 3 POH.
  6. The method of claim 5,
    Anionic polymers include acacia, alginate, carrageenan, chondroitin sulfate, carboxylmethylcellulose, dextran sulfate, fucoidan, gellan gum (gellan gum), heparin, hyaluronic acid, pectin, xanthane, xylan, polystyrene sulfonate, collagen, polyacrylic acid acrylic acid, polyphosphoric acid, polyphosphate, poly (lactide) and poly (lactide-co-glycolic acid) At least one composite particle selected from the group consisting of.
  7. The method of claim 1,
    Cationic polymer and anionic polymer is a composite particle contained in a weight ratio of 1:10 ~ 10: 1.
  8. The method of claim 1,
    Composite particles having a particle size of 2 to 10 μm.
  9. The method of claim 1,
    A multiparticulate further comprising a pharmaceutically active ingredient encapsulated in the core of the multiparticulate or mixed in a shell.
  10. In preparing the core-shell structured composite particles by electrospraying a crosslinkable cationic polymer or anionic polymer solution through two co-axial nozzles,
    A method for producing a composite particle according to claim 1, comprising the step of producing the composite particle crosslinked by reacting the composite particle with water.
  11. The method of claim 10,
    Cationic polymer and anionic polymer is a method for producing a composite particle is mixed in a weight ratio of 1:10 ~ 10: 1.
  12. The method of claim 10,
    Cationic polymer or anionic polymer solution is a method for producing a composite particle further comprises a pharmaceutically active ingredient.
  13. The method of claim 10,
    Electrospray drying conditions are liquid temperature of 0.25 to 70 mL / min, air flow of 1.5 to 110 L / min, voltage of 0.5 to 10 kV at a temperature of 40 to 150 ℃ method of producing a composite particle.
  14. delete
  15. The method of claim 10,
    The crosslinking reaction is carried out at 20 to 50 ° C. for 30 minutes to 12 hours.
  16. The composite particle of claim 1; And
    Drug delivery agent comprising a pharmaceutically active ingredient.
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20190036370A (en) 2017-09-27 2019-04-04 서원대학교산학협력단 Drug Delivery System for Sustained Release Formaulation of Drugs

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US6511749B1 (en) 1987-05-01 2003-01-28 Brown University Research Foundation Preparation of multiwall polymeric microcapsules from hydrophilic polymers
US7157102B1 (en) 2002-05-31 2007-01-02 Biotek, Inc. Multi-layered microcapsules and method of preparing same
WO2008008139A2 (en) 2006-07-12 2008-01-17 Abbott Cardiovascular Systems Inc. Methods and devices for forming treatment agent carriers
US20090035381A1 (en) * 2007-08-01 2009-02-05 Stankus John J Electrospraying method for fabrication of particles and coatings and treatment methods thereof

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6511749B1 (en) 1987-05-01 2003-01-28 Brown University Research Foundation Preparation of multiwall polymeric microcapsules from hydrophilic polymers
US7157102B1 (en) 2002-05-31 2007-01-02 Biotek, Inc. Multi-layered microcapsules and method of preparing same
WO2008008139A2 (en) 2006-07-12 2008-01-17 Abbott Cardiovascular Systems Inc. Methods and devices for forming treatment agent carriers
US20090035381A1 (en) * 2007-08-01 2009-02-05 Stankus John J Electrospraying method for fabrication of particles and coatings and treatment methods thereof

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20190036370A (en) 2017-09-27 2019-04-04 서원대학교산학협력단 Drug Delivery System for Sustained Release Formaulation of Drugs

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