EP3512529A1 - Drug delivery compositions and methods - Google Patents
Drug delivery compositions and methodsInfo
- Publication number
- EP3512529A1 EP3512529A1 EP16916372.2A EP16916372A EP3512529A1 EP 3512529 A1 EP3512529 A1 EP 3512529A1 EP 16916372 A EP16916372 A EP 16916372A EP 3512529 A1 EP3512529 A1 EP 3512529A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- drug delivery
- amino acid
- functional group
- delivery composition
- triple salt
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
Classifications
-
- 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
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/18—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons containing inorganic materials
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/04—Sulfur, selenium or tellurium; Compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/40—Peroxides
-
- 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
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/22—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons containing macromolecular materials
- A61L15/26—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives thereof
-
- 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
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/22—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons containing macromolecular materials
- A61L15/32—Proteins, polypeptides; Degradation products or derivatives thereof, e.g. albumin, collagen, fibrin, gelatin
-
- 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
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/42—Use of materials characterised by their function or physical properties
- A61L15/46—Deodorants or malodour counteractants, e.g. to inhibit the formation of ammonia or bacteria
-
- 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
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/20—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials
- A61L2300/21—Acids
- A61L2300/214—Amino acids
-
- 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
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
- A61L2300/404—Biocides, antimicrobial agents, antiseptic agents
Definitions
- This application is directed to drug delivery compositions and to methods for making and using the same, and more particularly to drug delivery compositions for wound treatment and to methods for making and using the same.
- the healing of a wound is a process that goes through a series of stages with varying cell types and chemical mediators in an appropriately moist environment. During this process, a wound site that is too moist or too dry may lead to inadequate cell proliferation. Traditional bandages have been used in an effort to retain appropriate levels of moisture but are inadequate in many cases for a variety of reasons.
- bacteria are a significant concern during wound healing, as uncontrolled populations of bacteria, which naturally contaminate all wounds, may give rise to an infection with potentially catastrophic consequences. This problem is complicated by the variety of bacteria which may be present, the increasing occurrence of drug -resistant bacteria, and patient drug allergies. While bandages again have been used to keep additional contamination from reaching the wound, they are again largely ineffective in many cases and further have little or no impact on contamination existing prior to bandage application.
- Oxidative bursts in certain cells such as macrophages of the vertebrate immune system, naturally produce a variety of highly reactive oxygenated species which can control bacterial populations.
- the amount of naturally occurring oxidative bursts is sometimes inadequate to quickly resolve contamination. This leads to greater possibility of infection, particularly where environments having lesser or greater moisture undesirably result in slower healing.
- a drug delivery composition includes a triple salt proxy functional group and at least one amino acid functional group.
- a method of forming a drug delivery composition includes reacting a triple salt with at least one amino acid in an aqueous environment.
- a biodegradable fabric includes a polymerized structure of a triple salt proxy functional group and at least one amino acid functional group.
- FIGS. 1 A and B show thermographs comparing the melting of (1 A) lysine and (IB) a lysine-based drug delivery composition, according to an embodiment of the disclosure.
- FIG. 2 shows thermographs comparing the thermal stability of (a) lysine and (b) a lysine-based drug delivery composition, according to an embodiment of the disclosure.
- FIGS. 3A and B show thermographs comparing the melting of (3A) glutamine and (3B) a glutamine-based drug delivery composition, according to an embodiment of the disclosure.
- the drug delivery compositions disclosed herein are compounds that simultaneously provide the health benefits of an amino acid as well as antimicrobial properties approximating the qualities of stable peroxides produced by oxidative bursts.
- the drug delivery compositions include a triple salt proxy functional group and at least one amino acid functional group.
- the triple salt proxy functional group includes a peroxy moiety.
- the at least one amino acid functional group of the compound includes amino acid health benefits.
- Amino acids are necessary for the synthesis of proteins, to provide nitrogen- bases energy for mitochondria for cell proliferation, to stop or reduce inflammation, to replace or repair damaged cells and to help cells synthesize extracellular matrix and collagen.
- amino acids contribute to wound angiogenesis, which may be initiated by the early release of growth factors, such as fibroblast growth factor-2 (FGF-2) and vascular endothelial growth factors (VEGF) for wound healing processes.
- FGF-2 fibroblast growth factor-2
- VEGF vascular endothelial growth factors
- amino acid health benefits encompass health-related properties such as, but not limited to, stopping or reducing inflammation of the wound, replacing or repairing damaged cells at the wound, stimulating cells to synthesize extracellular matrix, stimulating cells to synthesize collagen, and combinations thereof.
- Amino acids which may be employed in the compounds of exemplary embodiments include, but are not limited to, glutamine, alanine, aspartic acid, lysine, glycine, cysteine, arginine, proline, and combinations thereof (such as peptides, naturally occurring or artificial).
- amino acid functional group refers to the derivative form of an amino acid resulting from the reaction of the amino acid with a triple salt. Without being bound by theory, it is believed that the amino acid functional group may be a protonated amino acid.
- the drug delivery composition includes a plurality of amino acid functional groups.
- Triple salts disassociate highly reactive oxygenated species when exposed to an environment with elevated moisture levels and may approximate the effects of naturally occurring oxidative bursts. Triple salts possess only limited antimicrobial efficacy, due in part to the very slow rate of solid to liquid transformation of triple salts when exposed to elevated moisture levels. Further, triple salts have limited shelf life and contain hazardous impurities, including, but not limited to, irritants. In exemplary embodiments, these limitations of neat triple salts are overcome while the benefits are retained by compounding a triple salt proxy functional group with at least one amino acid functional group.
- the triple salt proxy functional group is a highly reactive oxygenated species capable of killing bacteria, fungi, and viruses with a high kill rate.
- the triple salt proxy functional group may also provide intracellular chemical energy transfer for cellular metabolism.
- the triple salt proxy functional group may stimulate cellular respiration.
- the triple salt proxy functional group may also stimulate the physiological process through which new blood vessels are formed from pre-existing vessels. Further, the triple salt proxy functional group may increase collagen deposition in the wound by increasing oxygenation of the wound.
- the triple salt proxy functional group exhibits broad spectrum antimicrobial activity against bacteria, fungi, viruses, or combinations thereof, including, but not limited to, killing Staphylococcus Aureus (MRSA), Salmonella typhimurium, Pseudomonas aerugionosa, Klebsiella pneumonia, Escherichia coli, Enterococcus, Enterobacter cloacae, Corynebacterium, pseudodiptherium, Corynebacterium pseudodiptherium, Candida albicans, and Hepatitis A virus (HAv).
- MRSA Staphylococcus Aureus
- Salmonella typhimurium Pseudomonas aerugionosa
- Klebsiella pneumonia Escherichia coli
- Enterococcus Enterobacter cloacae
- Corynebacterium, pseudodiptherium, Corynebacterium pseudodiptherium, Candida albicans and Hepatitis A virus (HAv).
- MRSA
- triple salt or peroxide including, but not limited to, sodium, magnesium and calcium peroxides with peroxy active chemistry which are biologically safe for mammals may be used to provide the triple salt proxy functional group of the compound in accordance with exemplary embodiments.
- Suitable triple salts include, but are not limited to, potassium peroxymonosulfate, which has the stoichiometry (K + HS05 ⁇ ) 2 (K + HS04 ⁇ ) (K 2 + S04 2" ), and which results in the triple salt proxy functional group of K + HS0 5 " .
- the compound in accordance with exemplary embodiments may be formulated through a variety of mechanisms, typically via wet chemistry synthesis.
- at least one amino acid is mixed with the triple salt, followed by reaction in an aqueous environment to preferentially dissolve the triple salt, which immediately interacts with the at least one amino acid to form a slurry.
- the triple salt may be dissolved in an aqueous environment first, followed by subsequent addition of the at least one amino acid to form the compound in a liquid slurry. The triple salt may be reacted with a plurality of amino acids in the aqueous environment.
- FTIR Fourier Transform Infrared
- the resulting compound may be stored in any suitable form, including, but not limited to, a liquid, freeze-dried, filtered and dried for storage as a powder base material, or incorporated into a medical foam.
- the powder base material includes the property of rapid solubility in an aqueous solution.
- the compound is stable for long periods of time without significant reduction in the antimicrobial properties stemming from the triple salt proxy functional group or the healing properties stemming from the at least one amino acid functional group.
- the drug delivery composition loses less than 0.1% of its antimicrobial activity per month when stored in a hermetically sealed enclosure.
- the drug delivery composition may, depending upon the form selected, be incorporated into any suitable medical product.
- exemplary products include, but are not limited to, disposable nonwoven medical fabrics, biodegradable wound dressings, foam wound dressings, composite wound dressings, surgical pads, post-operative dressings, nasal packing for ENT applications, and face masks.
- a biodegradable fabric includes the polymerized structure of a triple salt proxy functional group and at least one amino acid functional group having rubberlike characteristics.
- a powder base form of the drug delivery composition is incorporated within a fiber by powder or solution blending and extrusion to fiber form.
- fibers are formed by electrospinning a solution including the drug delivery composition. Fibers including the drug delivery composition may include surfaces which are the active site to deliver the drug delivery composition for healing purposes.
- Top coating synthetic or natural fabrics with the drug delivery composition may form a drug delivery layer which is biodegradable and which may be consumed during the duration of a healing process.
- the drug delivery layer is applied to any suitable fabric, including, but not limited to, hyaluronic acid-based fabric, including, but not limited to, non-woven fabric and scaffold fabric, non-woven fabric, polyurethane foam fabric, polyolefin fabric, cotton-based fabric, semi-permeable fabric, silicone-based fabric, foam fabric, alginate fabric, hydrogel fabric, hydrocolloid fabric, capillary action fabric, hydrofiber fabric, carbon/charcoal-enriched fabric, honey enriched fabric, silver impregnated fabric, biodegradable fabric, wound dressing fabric in single or multilayered composite forms, any other fabrics that are currently being used for wound dressing, and combinations thereof.
- hyaluronic acid-based fabric including, but not limited to, non-woven fabric and scaffold fabric, non-woven fabric, polyurethane foam fabric, polyolefin fabric, cotton-based fabric, semi-
- the drug delivery layer may be applied to cover continuously the entire surface of a fabric or may be applied in a specific pattern designed to optimize delivery of the drug delivery compound for healing purposes.
- the drug delivery composition is applied to a fabric as a solution and then freeze dried to an embedded powder form.
- the triple salt proxy functional group of the polymerized structure is K + HS0 5 " , or any suitable triple salt proxy functional group.
- the amino acid functional group of the polymerized structure is selected from the group consisting of derivatives of glutamine, alanine, aspartic acid, lysine, glycine, cysteine, arginine, proline, and combinations thereof (such as derivatives of peptides, naturally occurring or artificial).
- the biodegradable fabric including the polymerized structure may include the property of broad spectrum antimicrobial activities against bacteria, fungi and viruses, the property of amino acid health benefits, or both.
- Foam applications are preferred in many cases, as current medical foam products may be constructed with varying absorptive properties that may be adapted to heavily, moderately, or mildly exudative wounds to enable better moisture control, which may help enhance performance of the exemplary compounds.
- the drug delivery composition may be utilized for any suitable purpose, including, but not limited to, diabetic wound healing, liquid and solid base disinfection with rapid kill rate and environmentally safe profile, anti-scar applications, nasal liquid and solid base dispensing delivery, and liquid base wound cleaning with multiple functionality.
- a method of treating an individual having a wound includes introducing the drug delivery composition into the wound.
- the amount of drug delivery composition introduced into the wound may be any suitable and medically effective amount.
- the powder base material was collected in a resealable plastic bag, and stored in a plastic bucket with anhydrous calcium sulfate desiccant material (Drierite ® , W. A. Hammond Drierite Co. Ltd., Xenia, Ohio) placed in the bottom of the bucket.
- the bucket was closed with an air-tight lid.
- the activity of the triple salt proxy functional group decreased by less than 0.1% per month over the course of a year.
- thermographs compare the melting of (1A) lysine and (IB) a lysine-based drug delivery composition, according to this example.
- the thermographs demonstrate the melting point of the lysine- based drug delivery composition is about 191 °C, as compared to lysine which has a melting point of 209 °C.
- thermal gravimetric analysis thermographs show that the thermal stability of the lysine-based drug delivery composition (onset decomposition temperature of about 200 °C) is significantly lower than the thermal stability of lysine (onset decomposition temperature of about 257 °C).
- the lysine in the lysine-based drug delivery composition is nano-sized and uniformly distributed, and therefore not subject to significant agglomeration of the amino acid.
- thermographs compare the melting of (3A) glutamine and (3B) a glutamine-based drug delivery composition, according to this example.
- the thermographs demonstrate the melting point of the glutamine-based drug delivery composition is about 189 °C, as compared to glutamine which has a melting point of 190 °C.
- Antimicrobial activity for the drug delivery compositions of Examples 1 and 3 was measured with standard Kirby-Bauer antibiotic testing for Staphylococcus aureus (MRSA) and Pseudomonas aeruginosa.
- Kirby-Bauer antibiotic testing (KB testing or disk diffusion antibiotic sensitivity testing) is a test which uses antibiotic-impregnated wafers to test whether particular bacteria are susceptible to specific antibiotics. A known quantity of bacteria is grown on agar plates in the presence of thin wafers or powder base materials containing relevant antibiotics. If the bacteria are susceptible to a particular antibiotic, an area of clearing surrounds the wafer where bacteria are not capable of growing (called a zone of inhibition).
- the bacteria in question are swabbed uniformly across a culture plate. Five milligrams of powder base materials are then placed on the surface of the agar. The compound diffuses from the powder into the agar. The concentration of the compound will be highest next to the disk, and will decrease as distance from the disk increases. If the compound is effective against bacteria at a certain concentration, no colonies will grow where the concentration in the agar is greater than or equal to the effective concentration. This is the zone of inhibition. This, along with the rate of antibiotic diffusion, is used to estimate the bacteria's sensitivity to that particular antibiotic. In general, larger zones correlate with smaller minimum inhibitory concentration (MIC) of antibiotic for that bacterium. Inhibition produced by the test is compared with that produced by known concentration of a reference compound.
- MIC minimum inhibitory concentration
- Control dishes were fed with growth media, and treated cells were fed with growth media supplemented by ATCC 4330 4 mg/mL, ATCC 4330 8 mg/mL, GLN 1 mg/mL, or GLN 2.5 mg/mL, respectively. After two hours, cells were observed and a cell count was performed using trypan blue exclusion dye. Cells appeared healthy in all conditions and cell counts did not differ significantly, indicating that the drug delivery composition is not cytotoxic.
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Hematology (AREA)
- Inorganic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Dermatology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
Abstract
Description
Claims
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/US2016/052240 WO2018052443A1 (en) | 2016-09-16 | 2016-09-16 | Drug delivery compositions and methods |
Publications (2)
Publication Number | Publication Date |
---|---|
EP3512529A1 true EP3512529A1 (en) | 2019-07-24 |
EP3512529A4 EP3512529A4 (en) | 2020-05-06 |
Family
ID=61619222
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP16916372.2A Withdrawn EP3512529A4 (en) | 2016-09-16 | 2016-09-16 | Drug delivery compositions and methods |
Country Status (2)
Country | Link |
---|---|
EP (1) | EP3512529A4 (en) |
WO (1) | WO2018052443A1 (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109069706A (en) * | 2016-05-03 | 2018-12-21 | 蒂瑞克斯股份有限公司 | Hemostasis device and application method |
US11471570B2 (en) | 2016-05-03 | 2022-10-18 | Medtronic, Inc. | Hemostatic devices and methods of use |
US11577010B2 (en) | 2016-05-03 | 2023-02-14 | Medtronic, Inc. | Hemostatic devices and methods of use |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP4294183A1 (en) * | 2021-02-17 | 2023-12-27 | Oxion Dental, LLC | Stabilized active oxygen-generating antiseptic compositions, irrigation solutions, and articles |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4725576A (en) * | 1983-12-29 | 1988-02-16 | Research Foundation Of State University Of New York | Fungicidal polypeptide compositions containing L-histidine and methods for use therefore |
US6361551B1 (en) * | 1998-12-11 | 2002-03-26 | C. R. Bard, Inc. | Collagen hemostatic fibers |
AU2009212337B2 (en) * | 2008-02-08 | 2012-01-12 | Colgate-Palmolive Company | Cleaning compositions and methods |
EP2186411A1 (en) * | 2008-09-17 | 2010-05-19 | Taminco | Antimicrobial composition |
US20120074014A1 (en) * | 2010-09-27 | 2012-03-29 | Lutran Industries, Inc. | Product typically based on salt of peroxymonosulfuric acid and suitable for medicinal usage, and associated product fabrication |
US10383894B2 (en) * | 2010-03-17 | 2019-08-20 | Lutran Industries, Inc. | Human medicinal treatment using salt of peroxymonosulfuric acid |
-
2016
- 2016-09-16 EP EP16916372.2A patent/EP3512529A4/en not_active Withdrawn
- 2016-09-16 WO PCT/US2016/052240 patent/WO2018052443A1/en unknown
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109069706A (en) * | 2016-05-03 | 2018-12-21 | 蒂瑞克斯股份有限公司 | Hemostasis device and application method |
US11471570B2 (en) | 2016-05-03 | 2022-10-18 | Medtronic, Inc. | Hemostatic devices and methods of use |
US11577010B2 (en) | 2016-05-03 | 2023-02-14 | Medtronic, Inc. | Hemostatic devices and methods of use |
Also Published As
Publication number | Publication date |
---|---|
EP3512529A4 (en) | 2020-05-06 |
WO2018052443A1 (en) | 2018-03-22 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Prakash et al. | PVA/alginate/hydroxyapatite films for controlled release of amoxicillin for the treatment of periodontal defects | |
Khampieng et al. | Silver nanoparticles-based hydrogel: Characterization of material parameters for pressure ulcer dressing applications | |
CN108135745A (en) | Composition is formed for effective novel fast deposition film for the treatment of of wounds | |
EP2515869B1 (en) | Wound care products | |
EP3512529A1 (en) | Drug delivery compositions and methods | |
AU2008259660B2 (en) | Novel active ingredient in cicatrization and use thereof | |
KR20130085245A (en) | Antimicrobial wound dressing and preparing method of the same | |
ES2836299T3 (en) | Antimicrobial compositions | |
US20080020025A1 (en) | Composition for wound care and method of using same | |
EP2827912B1 (en) | Polymeric composite materials with antimicrobial and biodegradable properties and uses thereof | |
JP2018522701A (en) | Wound care products containing alexidine | |
EP3040087B1 (en) | Wound dressings | |
US20170000824A1 (en) | Drug delivery compositions and methods | |
Rathore et al. | Fabrication and characterization of chitosan film impregnated ciprofloxacin drug: A comparative study | |
EP3378503A2 (en) | Calcium based clinical material with antimicrobial properties and method of forming for prevention or treatment of infection | |
WO2019040185A1 (en) | Buckwheat honey and povidone-iodine wound-healing dressing | |
CN113476611B (en) | A composition with skin repairing effect | |
CN108578753B (en) | Bactericidal dressing and preparation method thereof | |
EP2699232B1 (en) | Improved wound care product | |
CN109200326A (en) | Dressing and bandage for wound healing | |
Chakravarty et al. | Properties of solvent-cast chitin membranes and exploration of potential applications | |
JP6456897B2 (en) | Wound healing agent having antibacterial properties and promoting wound healing | |
RU2396984C2 (en) | Antimicrobial haemostatic sponge | |
CN103285418A (en) | Novel biological antibacterial dressing aerosol based on large-area burn wound | |
RU2736061C1 (en) | Method of producing biocomposite based on airgel of bacterial cellulose having haemostatic properties |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
17P | Request for examination filed |
Effective date: 20190404 |
|
AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR |
|
AX | Request for extension of the european patent |
Extension state: BA ME |
|
DAV | Request for validation of the european patent (deleted) | ||
DAX | Request for extension of the european patent (deleted) | ||
A4 | Supplementary search report drawn up and despatched |
Effective date: 20200402 |
|
RIC1 | Information provided on ipc code assigned before grant |
Ipc: A61K 33/04 20060101ALI20200328BHEP Ipc: A61K 33/40 20060101AFI20200328BHEP Ipc: A61L 15/46 20060101ALI20200328BHEP Ipc: A61L 15/18 20060101ALI20200328BHEP Ipc: A61P 17/02 20060101ALI20200328BHEP Ipc: A61L 15/26 20060101ALI20200328BHEP Ipc: A61L 15/32 20060101ALI20200328BHEP |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION HAS BEEN WITHDRAWN |
|
18W | Application withdrawn |
Effective date: 20200819 |