US20140287061A1 - In-situ cross-linkable polymeric compositions and methods thereof - Google Patents

In-situ cross-linkable polymeric compositions and methods thereof Download PDF

Info

Publication number
US20140287061A1
US20140287061A1 US14/357,342 US201214357342A US2014287061A1 US 20140287061 A1 US20140287061 A1 US 20140287061A1 US 201214357342 A US201214357342 A US 201214357342A US 2014287061 A1 US2014287061 A1 US 2014287061A1
Authority
US
United States
Prior art keywords
polymer
polymeric composition
weight
biocompatible polymeric
cross
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.)
Abandoned
Application number
US14/357,342
Other languages
English (en)
Inventor
Joseph A. Landolina
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Cresilon Inc
Original Assignee
Suneris Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Suneris Inc filed Critical Suneris Inc
Priority to US14/357,342 priority Critical patent/US20140287061A1/en
Assigned to Suneris, Inc. reassignment Suneris, Inc. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: LANDOLINA, JOSEPH A
Assigned to Suneris, Inc. reassignment Suneris, Inc. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: LANDOLINA, JOSEPH A.
Publication of US20140287061A1 publication Critical patent/US20140287061A1/en
Assigned to CRESILON, INC. reassignment CRESILON, INC. CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). Assignors: Suneris, Inc.
Assigned to CRESILON, INC. reassignment CRESILON, INC. CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). Assignors: Suneris, Inc.
Priority to US15/266,813 priority patent/US9687584B1/en
Abandoned legal-status Critical Current

Links

Images

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
    • A61L26/00—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form
    • A61L26/0009—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form containing macromolecular materials
    • A61L26/0052—Mixtures of macromolecular compounds
    • 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
    • A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
    • 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
    • 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
    • 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
    • A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
    • A61L24/001—Use of materials characterised by their function or physical properties
    • 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
    • A61L26/00—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form
    • A61L26/0009—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form containing macromolecular materials
    • A61L26/0014—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form containing macromolecular materials obtained 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
    • A61L26/00—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form
    • A61L26/0009—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form containing macromolecular materials
    • A61L26/0023—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
    • A61L26/00—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form
    • A61L26/0061—Use of materials characterised by their function or physical properties
    • A61L26/0066—Medicaments; Biocides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
    • C08L5/04—Alginic acid; 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
    • A61L2400/00—Materials characterised by their function or physical properties
    • A61L2400/04—Materials for stopping bleeding

Definitions

  • the present invention relates generally to a composition using a biocompatible polymeric formulation and, in particular, to a hemophilic polymeric matrix for use in wound healing, blood coagulation, and cosmetic use.
  • Wound healing is an intricate, orchestrated process involving the interactions of various cells and matrix components to first establish a provisional tissue and then remodel this while forming the mature replacement.
  • the hemostatic platelet plug reestablishes the infection-limiting and desiccation-limiting barrier, and elicits the first wave of cellular infiltrates.
  • This consists mainly of leukocytes that provide both innate and acquired immunity. These cells produce enzymes and biocidal molecules to eliminate microbial contamination; however, these same defense mechanisms are detrimental to the keratinocytes, fibroblasts and endothelial cells required to regenerate the lost tissue.
  • the events and processes of the inflammatory phase need to regress.
  • a particular challenge is offered in the case of skin wound repair, which occurs at a contaminated surface. If a wound becomes infected, the normal healing is disrupted as the inflammatory phase becomes chronic, suppressing the regenerative phase. Further, the enzymes liberated by both the microbes and leukocytes break down the wound tissue as well as surrounding skin. Thus, it is critical to ensure proper healing to prevent infections being established by normal skin wound contaminants.
  • Fibronectin has been reported to be involved in each stage of the wound healing process, particularly by creating a scaffold to which the invading cells will adhere. Initially, there is a release of many mediators to the wound site, such as fibronectin and fibrinogen. Fibronectin promotes inflammatory cell migration into the wound and debris phagocytosis by monocytes. Thereafter, angiogenesis and reepithelialization take place. At this stage, fibronectin exerts chemotactic activity on endothelial cells, and promotes epithelial cell and fibroblast migration onto the basal membrane. Fibronectin also appears to be essential in the remodeling phase where it plays a major role in the organization of collagen fibrils. The fibrillar collagen ultimately forms fibrous bundles that enhance the tissue tensile strength, leading to would closure.
  • Hydrogels have typically been utilized as topical formulations for promoting the wound healing process.
  • the gel compositions have been selected for their properties of swelling degree, biocompatibility, permeability, and swelling kinetics. Examples of such compounds have included vinyl polymers (e.g. polyacrylic acid), cellulose, and cellulose derivatives.
  • vinyl polymers e.g. polyacrylic acid
  • cellulose e.g. cellulose
  • cellulose derivatives e.g. polyacrylic acid
  • Polyacrylic acid polymer also referred to as carbomer, has been used because of its superiority in delivering fibronectin to skin wounds.
  • Naturally occurring biopolymers have applications in tissue engineering, regenerative medicine, drug delivery, medical implant, plastic surgery, and others.
  • Such products have components including hyaluronic acid (HA), chitosan, heparin, chondroitin sulfate, alginate and other glucosamine and glycosaminoglycans, other polysaccharides, and derivatives thereof.
  • HA hyaluronic acid
  • chitosan chitosan
  • heparin chondroitin sulfate
  • alginate and other glucosamine and glycosaminoglycans other polysaccharides, and derivatives thereof.
  • fibronectin and similar proteins
  • alginate salt concentrations of fibronectin (and similar proteins) have been utilized with alginate salt to treat chronic ulcers.
  • the dressing system has been solidified, converting the gel into fibers, by a process of freeze-drying. This procedure creates a sponge-like structure with hydrophilic properties.
  • the dressings can return to a gel-like state, absorbing up to 20 times their weight in wound exudate.
  • the dressing is easily removed after the wound treatment because of its sponge-like structure and moisture retention.
  • the fibronectin-cellulose dressing does not provide the desired fibrous protective film on the surface of the deepithelialized human skin. Debridement is then performed upon removal of the dressing to remove any necrotic material.
  • Chronic wounds which would assist healing, decrease inflammation, reduce pain, and prevent scar formation with both acute and chronic wounds.
  • acute wounds that could be treated include burns, abrasions, dry skin, post-op surgical incisions, cuts, puncture wounds, blisters, insect bites, and other severe tissue injury.
  • Chronic wound treatment might encompass slow to heal wounds including pressure ulcers, venous ulcers, diabetic foot ulcers, decubitus ulcers, and non-healing tissue injuries.
  • composition that will be easily applied, forming a matrix conducive to the healing of a tissue, and having anti-microbial properties.
  • the composition may be biocompatible or quickly reacted to avoid possibilities of cytotoxicity. Further, the composition will stimulate and maximize wound healing while providing a controlled method for providing thin and thick layers of a solidified wound dressing, as desired.
  • Indirect effects may include reduced need for medical procedures such as debridement, decreased hospitalization time, reduced postoperative recovery times, shortened return interval to daily functions and work, and reduced overall treatment costs. Desirably, these improvements to wound healing, including application and method of use, will be valuable in treating and repairing various tissue(s).
  • the following invention is a biocompatible polymeric composition that is a gelatinous wound healing and hemostatic matrix able to be formed and solidified both internally and externally.
  • the biocompatible polymeric composition comprises 1) one or more than one polyanionic polymer and 2) one or more than one polycationic polymer.
  • the one or more than one polyanionic polymer includes at least one cross-linkable polyanionic polymer.
  • the one or more than one polyanionic polymer includes at least one cross-linkable polyanionic polymer and at least one non-cross-linkable polyanionic polymer.
  • the biocompatible polymeric composition comprises a mixture of 1) one or more than one polyanionic polymer able to be formed on the surface of a wound and 2) one or more than one polycationic polymer that assists in the solidification process as well as speeds up blood clotting.
  • the biocompatible polymeric composition comprises a mixture of 1) one or more than one polyanionic polymer able to be formed on the surface of a wound; 2) one or more than one polycationic polymer that assists in the solidification process as well as speeds up blood clotting; and 3) a cross-linking mist that cross-links the gel in the wound while disinfecting the surrounding area.
  • the one or more than one polyanionic polymer comprises alginates or hyaluronates. In one embodiment of the invention, the one or more than one polycationic polymer comprises chitosan. In one embodiment of the invention, the cross-linking mist may be aqueous calcium chloride.
  • One or more methods of using the medical gel of the invention are also disclosed, including rapidly achieving hemostasis without the need to apply pressure, and providing a biocompatible wound healing matrix.
  • Various embodiments of the invention allow the formulation to be adjusted and implemented for varying the desired viscosity and pre-determined characteristic functions.
  • the ratio of the polycationic polymer to the polyanionic polymer may be improved, having varying degrees of efficiency in wound healing.
  • therapeutics can be added to integrate drug formulations for drug delivery options.
  • other features may encompass controlling temperature(s) and/or pressure(s) during the preparation of the medical gel, during application of the gel, and implementing a control for the elasticity or rigidity of the solidified matrix.
  • the matrix formulation, both liquid and solidified structures, may also be dependent on anatomical and physiological measurements and conditions.
  • compositions allow the composition to be adjusted and implemented at a first tissue site or a second tissue site, and such modification deemed obvious may be integrated and combined in varying quantities to provide for a structural matrix of any size, shape, and configuration.
  • FIG. 1 is a side view of an embodiment of the present invention.
  • FIG. 2 is a microscopic depiction of how the present invention interacts with blood and itself.
  • FIGS. 3A to 3I show various polymeric subunits that can be used to make up the polycationic or polyanionic polymers.
  • FIG. 4 shows the benefits of the present invention as compared to existing technology.
  • Biocompatible polymeric compositions of the present invention may be used to treat external wounds as well as internal wounds.
  • the biocompatible polymeric composition may be applied to a variety of wounds.
  • wounds include, but are not limited to: an external laceration, an abrasion, a burn, an ocular laceration, damage to a parenchymal organ, an internal laceration, a laceration in the gastrointestinal tract, superficial cuts and scrapes, internal bleeding, an arterial bleed, a venous bleed, dental or oral bleeds and incisions.
  • Subjects who can benefit from such wound treatment include a variety of animals including humans, mammals such as horses, sheep, cattle, hogs, dogs, cats, and marine animals such as whales, dolphins, seals, otters, fish, and reptiles such as turtles.
  • FIG. 1 An illustration of a structural matrix in accordance with one embodiment of the invention is shown in FIG. 1 .
  • a damaged section of tissue, wound ( 112 ) has vasculature ( 116 ) protruding throughout.
  • a biocompatible polymeric composition ( 114 ) has been applied to the wound ( 112 ), which has been coated with protective coat ( 110 ).
  • FIG. 2 shows a magnified view of one embodiment of biocompatible polymeric composition ( 114 ), which comprises structural polymer ( 226 ) and hemophilic polymer ( 224 ).
  • Structural polymer ( 226 ) comprises about 0.1% to 95% by total composition weight of a cross-linkable polyanionic polymer and 0% to 95% by total composition weight of a non-cross-linkable polyanionic polymer.
  • Hemophilic polymer ( 224 ) comprises about 1% to 90% by total composition weight of a polycationic polymer.
  • Red blood cell ( 210 ) is shown in relation to the cationic function groups ( 212 ) via a red blood cell-cationic group linkage ( 216 ).
  • FIGS. 3A to 3I show various polymers that can be chosen as structural polymer ( 226 ) or hemophilic polymer ( 224 ). Polymers can be modified through the addition of carboxymethyl (CM) groups to gain anionic functional groups ( 218 ).
  • FIG. 3E shows carboxymethyl cellulose. Alginate ( 3 A), sodium hyaluronate ( 3 F), ⁇ -carrageenan ( 3 G), ⁇ -carrageenan ( 3 H), and sodium polyacrylate ( 3 I) are examples of polymers that would function as structural polymer ( 226 ).
  • chitin ( 3 B) and chitosan ( 3 C) are examples of polymers that would function as hemophilic polymer ( 224 ).
  • FIG. 3D shows how any polymer ( 340 ) can be modified with a diethylaminoethyl (DEAE) group to gain cationic functional groups ( 212 ).
  • DEAE diethylaminoethyl
  • Biocompatible polymeric composition ( 114 ) contains about 0.1% to 99.8% by total composition weight of a solvent.
  • the solvent is ethanol.
  • the solvent is a 5% aqueous solution of ethanol in water.
  • Non-limiting examples of solvents include water, ethanol, amyl acetate, acetone, methyl ethyl ketone, isopropanol, and tetrahydrofuran.
  • structural polymer ( 226 ) and hemophilic polymer ( 224 ) experience intermolecular interactions which bind them together.
  • hemophilic polymer ( 224 ) attract anionic functional groups ( 218 ) on structural polymer ( 226 ) and result in ionic cross-linking ( 214 ). Additionally, hemophilic polymer ( 224 ) and structural polymer ( 226 ) can be covalently cross-linked ( 228 ), similar to a Schiff base or azomethine linkage.
  • Protective coat ( 110 ) comprises 0.1% to 30% by weight of a di- or higher valent cation ( 220 ), 0% to 90% by weight of a hydrophobic polymer, and 5% to 99.9% by weight of a solvent.
  • Protective coat ( 110 ) cross-links composition ( 114 ) by diffusing divalent cation ( 220 ) inwards, which results in divalent cation cross-linking ( 222 ) of structural polymer ( 226 ). This increases the rigidity of composition ( 114 ) and allows for better stability.
  • Protective coat ( 110 ) can also contain hydrophobic polymers, which limit the water loss from composition ( 114 ) and improve durability.
  • the hydrophobic polymer may be a polyurethane, nitrocellulose, a cyanoacrylate, a styrene, a polytetrafluoroethane, and a silicone, and combinations thereof.
  • the solvent may be water, amyl acetate, acetone, methyl ethyl ketone, isopropanol, and tetrahydrofuran, and combinations thereof.
  • the di- or higher valent cation may be Ca2+, Fe2+, Fe3+, Ag2+, Ag3+, Au2+, Au3+, Mg2+, Cu2+, Cu3+, and Zn2+. In one embodiment of the invention, the cation is Ca2+.
  • structural polymer ( 226 ) comprises 0.1% to 5% by weight of sodium alginate and 1% to 5% by weight of sodium hyaluronate
  • hemophilic polymer ( 224 ) comprises 2% to 25% by weight of chitosan chloride
  • the solvent comprises 65% to 96.9% by weight of a 5% aqueous solution of ethanol in water.
  • the composition functions as a wound healing matrix to facilitate faster tissue regeneration.
  • structural polymer ( 226 ) comprises 2% to 5% by weight of sodium alginate and 0% to 2% by weight of sodium hyaluronate
  • hemophilic polymer ( 224 ) comprises 5% to 20% by weight of chitosan chloride
  • the solvent comprises 73% to 93% by weight of a 5% aqueous solution of ethanol in water.
  • the composition functions as a thick gel for rapidly achieving hemostasis without the need to apply pressure.
  • the composition can be delivered topically to the compromised blood vessel.
  • structural polymer ( 226 ) comprises 0.1% to 4% by weight of sodium alginate and 1% to 5% by weight of a lysine-rich polypeptide
  • hemophilic polymer ( 224 ) comprises 5% to 25% by weight of diethylaminoethyl-dextran (DEAE-Dextran)
  • the solvent comprises 65% to 93% by weight of a 5% aqueous solution of ethanol in water.
  • the biocompatible polymeric composite ( 114 ) is then cross-linked in situ by applying an aerosol mist comprising 0.1% to 1% by weight of calcium chloride, 1% to 5% by weight of nitrocellulose, and 94% to 98.9% by weight of amyl acetate.
  • the composition functions as a protective covering for cuts and scrapes that is durable and limits water loss from the wound.
  • the biocompatible polymeric composition comprises about 3.6% by weight of sodium alginate, about 7% by weight of chitosan chloride, and about 89.4% by weight of a 5% aqueous solution of ethanol in water.
  • This embodiment may function as a composition to treat arterial bleeds.
  • the protective coat comprises a solution comprising about 0.1% to about 30% by weight of a di- or higher valent cation; 0% to about 90% by weight of a hydrophobic polymer; and about 5% to about 99.9% by weight of a solvent.
  • the protective coat comprises a solution comprising about 0.1% to about 1% by weight of a di-valent cation; about 1 to about 5% by weight of a hydrophobic polymer; and about 94% to about 98.9% by weight of a solvent.
  • composition ( 114 ) is used as a carrier for a therapeutic agent such as a drug or biologic molecule.
  • a therapeutic agent such as a drug or biologic molecule.
  • protective coat ( 110 ) is prepared with a salt of silver, increasing the antimicrobial properties of the gel.
  • the therapeutic agent is selected from the group consisting of: antimicrobial agents, antibiotics, hormones, proteins (such as calreticulin, thrombin, prothrombin, Factor VIII), and iodine, and combinations thereof.
  • the therapeutic agent is preferably iodine.
  • the therapeutic agent is a protein.
  • the cross-linkable polyanionic polymer may be a polystyrene sulfonate (such as sodium polystyrene sulfonate), a polyacrylate (such as sodium polyacrylate), a polymethacrylate (such as sodium polymethacrylate), a polyvinyl sulphate (such as sodium polyvinyl sulphate), a polyphosphate (such as sodium polyphosphate), Iota carrageenan, Kappa carrageenan, gellan gum, carboxyl methyl cellulose, carboxyl methyl agarose, carboxyl methyl dextran, carboxyl methyl chitin, carboxyl methyl chitosan, a polymer modified with a carboxyl methyl group, an alginate (such as sodium alginate), a polymer containing a plurality of carboxylate groups, a xanthan gum, and combinations thereof.
  • the crosslinkable polyanionic polymer is an alginate (such as sodium alg
  • the cross-linkable polyanionic polymer comprises about 1% to about 95% by weight of the biocompatible polymeric composition; preferably the cross-linkable polyanionic polymer comprises about 5% to about 40% by weight of the biocompatible polymeric composition; preferably the cross-linkable polyanionic polymer comprises about 10% to about 30% by weight of the biocompatible polymeric composition.
  • the non-cross-linkable polyanionic polymer may be a hyaluronate (such as sodium hyaluronate), a polynucleotide (such as RNA), a polypeptide chain having an average residue isoelectric point below 7, a glucosaminoglycan, and a proteoglycan, and combinations thereof.
  • a hyaluronate such as sodium hyaluronate
  • RNA polynucleotide
  • a polypeptide chain having an average residue isoelectric point below 7 a glucosaminoglycan
  • proteoglycan and combinations thereof.
  • the non-cross-linkable polyanionic polymer is a hyaluronate, more preferably sodium hyaluronate.
  • the non-cross-linkable polyanionic polymer comprises about 0 to about 95% by weight of the biocompatible polymeric composition; preferably the non-cross-linkable polyanionic polymer comprises about 5 to about 25% by weight of the biocompatible polymeric composition; preferably the non-cross-linkable polyanionic polymer comprises about 0 to about 5% by weight of the biocompatible polymeric composition; preferably the non-cross-linkable polyanionic polymer comprises about 0 to about 2% by weight of the biocompatible polymeric composition; preferably the non-cross-linkable polyanionic polymer comprises about 1 to about 5% by weight of the biocompatible polymeric composition.
  • the polycationic polymer may be a chitosan (such as chitosan chloride), chitin, diethylaminoethyl-dextran, diethylaminoethyl-cellulose, diethylaminoethyl-agarose, diethylaminoethyl-alginate, a polymer modified with a diethylaminoethyl group, a polymer containing a plurality of protonated amino groups, and a polypeptide having an average residue isoelectric point above 7, and combinations thereof.
  • the polycationic polymer is a chitosan, more preferably chitosan chloride.
  • the polycationic polymer is diethylaminoethyl-dextran (DEAE-Dextran).
  • the polycationic polymer comprises about 1% to about 90% by weight of the biocompatible polymeric composition; preferably the polycationic polymer comprises about 2% to about 80% by weight of the biocompatible polymeric composition; preferably the polycationic polymer comprises about 2% to about 25% by weight of the biocompatible polymeric composition.
  • the individual components of the biocompatible polymeric composition may be stored in a variety of different containers for a variety of different applications, including for example, packets, sachets, tubes, tubs, pumps, syringes, bottles, bags, and aerosol-based spray cans.
  • the components may be stored in containers made of a variety of materials, including for example, plastic, metal, or glass.
  • the components may be provided in operably connected configurations, or as separate components for a user to set up prior to use.
  • compositions and systems described herein may be included in a kit or article of manufacture for forming a biocompatible polymeric composition
  • a biocompatible polymeric composition comprising one or more of: a solution comprising a polyanionic polymer; a solution comprising a polycationic polymer; a solvent; and a solution comprising a di- or higher valent cation, a hydrophobic polymer, and solvent.
  • the kit or article of manufacture may further contain gauze, bandages, tape, brushes, spatulas, and sponges.
  • the studies described may utilize one embodiment of the composition to form a rigid matrix while another composition may be designed with an increased elasticity, alone or in combination. Further, the methods of mixing and formulating the composition may be performed in any order and combination so as to achieve the same or similar effects of the embedded solidified matrix, the matrix integrating the formation of naturally restructuring tissue.
  • the one or more than one polyanionic polymer is first applied to a wound and then the one or more than one polycationic polymer is applied to the said one or more than one polymeric polymer at the wound site.
  • the one or more than one polyanionic polymer is mixed with the one or more than one polycationic polymer and then the mixture is then applied to the wound.
  • the one or more than one polyanionic polymer is applied to a wound at the same time, or about the same time, that the one or more than one polycationic polymer is applied to a wound.
  • a method of treating a wound comprises applying one or more than one polyanionic polymer to a wound and then applying one or more than one polycationic polymer to the said one or more than one polymeric polymer at the wound site.
  • a method of treating a wound comprises mixing one or more than one polyanionic polymer with one or more than one polycationic polymer and then applying the mixture to the wound.
  • a method of treating a wound comprises applying one or more than one polyanionic polymer to the wound at the same time, or about the same time, as one or more than one polycationic polymer is applied to a wound.

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • Epidemiology (AREA)
  • Materials Engineering (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Polymers & Plastics (AREA)
  • Surgery (AREA)
  • Inorganic Chemistry (AREA)
  • Hematology (AREA)
  • Diabetes (AREA)
  • Dermatology (AREA)
  • Materials For Medical Uses (AREA)
  • Medicinal Preparation (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Dental Preparations (AREA)
US14/357,342 2011-11-13 2012-11-12 In-situ cross-linkable polymeric compositions and methods thereof Abandoned US20140287061A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US14/357,342 US20140287061A1 (en) 2011-11-13 2012-11-12 In-situ cross-linkable polymeric compositions and methods thereof
US15/266,813 US9687584B1 (en) 2011-11-13 2016-09-15 In-situ cross-linkable polymeric compositions and methods thereof

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201161559110P 2011-11-13 2011-11-13
PCT/US2012/064670 WO2013071235A1 (fr) 2011-11-13 2012-11-12 Compositions polymères réticulables in situ et procédés associés
US14/357,342 US20140287061A1 (en) 2011-11-13 2012-11-12 In-situ cross-linkable polymeric compositions and methods thereof

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2012/064670 A-371-Of-International WO2013071235A1 (fr) 2011-11-13 2012-11-12 Compositions polymères réticulables in situ et procédés associés

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US15/266,813 Continuation US9687584B1 (en) 2011-11-13 2016-09-15 In-situ cross-linkable polymeric compositions and methods thereof

Publications (1)

Publication Number Publication Date
US20140287061A1 true US20140287061A1 (en) 2014-09-25

Family

ID=48290658

Family Applications (4)

Application Number Title Priority Date Filing Date
US14/357,342 Abandoned US20140287061A1 (en) 2011-11-13 2012-11-12 In-situ cross-linkable polymeric compositions and methods thereof
US15/266,813 Active US9687584B1 (en) 2011-11-13 2016-09-15 In-situ cross-linkable polymeric compositions and methods thereof
US15/611,418 Active US10850003B2 (en) 2011-11-13 2017-06-01 In-situ cross-linkable polymeric compositions and methods thereof
US17/084,518 Active US11383005B2 (en) 2011-11-13 2020-10-29 In-situ cross-linkable polymeric compositions and methods thereof

Family Applications After (3)

Application Number Title Priority Date Filing Date
US15/266,813 Active US9687584B1 (en) 2011-11-13 2016-09-15 In-situ cross-linkable polymeric compositions and methods thereof
US15/611,418 Active US10850003B2 (en) 2011-11-13 2017-06-01 In-situ cross-linkable polymeric compositions and methods thereof
US17/084,518 Active US11383005B2 (en) 2011-11-13 2020-10-29 In-situ cross-linkable polymeric compositions and methods thereof

Country Status (16)

Country Link
US (4) US20140287061A1 (fr)
EP (1) EP2776068A4 (fr)
JP (3) JP2014533181A (fr)
KR (1) KR20140090670A (fr)
CN (2) CN109602944A (fr)
AU (2) AU2012334982A1 (fr)
BR (1) BR112014011442A8 (fr)
CA (1) CA2855347C (fr)
HK (1) HK1201734A1 (fr)
IL (1) IL232330B (fr)
IN (1) IN2014CN03524A (fr)
MX (2) MX366366B (fr)
RU (2) RU2017144044A (fr)
SG (2) SG11201402279SA (fr)
WO (1) WO2013071235A1 (fr)
ZA (1) ZA201403166B (fr)

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9173971B2 (en) 2010-11-12 2015-11-03 University Of Utah Research Foundation Simple adhesive coacervates and methods of making and using thereof
US9272069B2 (en) 2008-01-24 2016-03-01 University Of Utah Research Foundation Adhesive complex coacervates and methods of making and using thereof
WO2016209198A1 (fr) * 2015-06-22 2016-12-29 Cresilion, Inc. Échafaudage polymère adhésif hémostatique hautement efficace
US20170128263A1 (en) * 2014-07-11 2017-05-11 National Institutes Of Health Surgical tool and method for ocular tissue transplantation
US9867899B2 (en) 2010-05-24 2018-01-16 University Of Utah Research Foundation Reinforced adhesive complex coacervates and methods of making and using thereof
US9913926B2 (en) 2008-01-24 2018-03-13 University Of Utah Research Foundation Adhesive complex coacervates and method of making and using thereof
US9913927B2 (en) 2014-07-14 2018-03-13 University Of Utah Research Foundation In situ solidifying complex coacervates and methods of making and using thereof
WO2018119320A1 (fr) * 2016-12-21 2018-06-28 Cresilon, Inc. Compositions hémostatiques comprenant des agents antifibrinolytiques
US10077324B2 (en) 2013-02-06 2018-09-18 Kci Licensing, Inc. Polymers, preparation and use thereof
US20190328933A1 (en) * 2018-01-26 2019-10-31 Polarityte, Inc. Composite-interfacing biomaterial accelerant substrate
US10660945B2 (en) 2015-08-07 2020-05-26 Victor Matthew Phillips Flowable hemostatic gel composition and its methods of use
US10751444B2 (en) 2015-08-07 2020-08-25 Victor Matthew Phillips Flowable hemostatic gel composition and its methods of use
US10850003B2 (en) 2011-11-13 2020-12-01 Cresilon, Inc. In-situ cross-linkable polymeric compositions and methods thereof
US11065337B2 (en) 2015-12-14 2021-07-20 University of Pittsburgh—of the Commonwealth System of Higher Education Complex coacervate for controlled release and related methods
US11266678B2 (en) * 2016-08-25 2022-03-08 Pharmaresearch Co., Ltd. Composition for articular cavity injection comprising nucleic acid and chitosan
US11298423B2 (en) * 2016-03-04 2022-04-12 University of Pittsburgh—of the Commonwealth System of Higher Education Protection and delivery of multiple therapeutic proteins
US11541151B2 (en) 2017-09-20 2023-01-03 Cha University Industry-Academic Cooperation Foundation Coacervate composition containing protein drug and wound healing agent comprising same
US11896234B2 (en) 2018-01-26 2024-02-13 Fluidx Medical Technology, Llc Apparatus and method of using in situ solidifying complex coacervates for vascular occlusion
US12016968B2 (en) 2020-12-23 2024-06-25 Cresilon, Inc. Highly efficacious hemostatic adhesive polymer scaffold

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ITTO20130375A1 (it) * 2013-05-10 2014-11-11 Marco Benzi Prodotto per l'uso per il trattamento terapeutico di parodontopatie e perimplantiti
CN103611180B (zh) * 2013-11-21 2015-02-18 无锡中科光远生物材料有限公司 一种自粘止血防粘连纤维体的制备方法
JP7493961B2 (ja) * 2015-06-22 2024-06-03 クレシロン， インコーポレイテッド 高度に有用な止血用接着性ポリマー足場
CN105030815B (zh) * 2015-08-10 2019-03-15 贵州扬生医用器材有限公司 一种手术冲洗液及其制法
KR101666792B1 (ko) * 2016-02-05 2016-10-17 주식회사 파마리서치프로덕트 핵산 및 키토산을 포함하는 온도감응성 하이드로겔 조성물
CN105860107B (zh) * 2016-04-26 2018-02-09 中南大学 一种过氧化氢响应及具有电化学活性的壳聚糖水凝胶的制备方法
WO2018128704A2 (fr) 2016-11-07 2018-07-12 3M Innovative Properties Company Composition médicale comprenant un ou des polymères contenant du guanidinyle et un ou des carraghénanes
IL249725A0 (en) 2016-12-22 2017-03-30 Omrix Biopharmaceuticals Ltd A hemostatic preparation containing an anion exchanger and a calcium salt
IL267432B1 (en) * 2016-12-22 2024-03-01 Omrix Biopharmaceuticals Ltd A hemostatic preparation containing an anion exchanger and a calcium salt
JP6939607B2 (ja) * 2017-03-27 2021-09-22 Jsr株式会社 組成物およびその用途
CN108926490B (zh) * 2017-05-25 2021-01-26 南方医科大学南方医院 一种抗凝胃管的制作方法
RU2675631C1 (ru) * 2018-10-02 2018-12-21 Общество с ограниченной ответственностью "Новые Биомедицинские Решения" Местное гемостатическое средство с повышенной антимикробной активностью
EP3946480A1 (fr) * 2019-04-03 2022-02-09 DTech - Società a Responsabilità Limitata Système à deux éléments pour le traitement thérapeutique de lésions cutanées et son procédé de production
CN110157010B (zh) * 2019-05-05 2021-04-02 上海交通大学 一种基于多糖/聚肽的聚电解质复合物水凝胶止血剂
CN111303453B (zh) * 2020-03-09 2021-06-04 中国海洋大学 一种多重敏感型水凝胶聚合物的制备方法和应用
EP3925636A1 (fr) 2020-06-17 2021-12-22 Centre Of Experimental Medicine Slovak Academy Of Sciences Institute Of Experimental Pharmacology Membranes composites contenant un cytoprotecteur à libération intelligente ciblant le tissu enflammé et leur utilisation
CN115887738B (zh) * 2022-12-16 2024-05-10 湖南师范大学 一种聚丙烯酰胺-壳聚糖/高岭土多孔材料及其制备方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5836970A (en) * 1996-08-02 1998-11-17 The Kendall Company Hemostatic wound dressing
US6150581A (en) * 1995-06-07 2000-11-21 United States Surgical Corporation Chitosan/alginate anti-adhesion barrier
US20110144229A1 (en) * 2008-08-19 2011-06-16 The Regents Of The University Of Michigan Biocompatible coatings, and methods of making and using the same

Family Cites Families (63)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS58206751A (ja) 1982-05-26 1983-12-02 日石三菱株式会社 創傷被覆材
JPS59139310A (ja) 1983-01-31 1984-08-10 Shiseido Co Ltd 乳化組成物
JPH0612993B2 (ja) 1987-08-10 1994-02-23 株式会社クラレ 球状の微生物固定化成形物の製造法
US4956350A (en) * 1988-08-18 1990-09-11 Minnesota Mining And Manufacturing Company Wound filling compositions
FI95207C (fi) 1992-09-14 1996-01-10 Novasso Oy Haavansuojaside
JP3411602B2 (ja) * 1992-10-22 2003-06-03 グンゼ株式会社 キトサンの溶解方法
DE4337152A1 (de) * 1993-10-30 1995-05-04 Merck Patent Gmbh Verfahren zur Herstellung von wäßrigen Chitosan-Lösungen und -Gelen
US5670169A (en) 1993-12-20 1997-09-23 E.R. Squibb & Sons, Inc. Wound hydrating gel with novel preservative system and low cytotoxicity
US20020032488A1 (en) 1994-05-13 2002-03-14 Brekke John H. Device for regeneration of articular cartilage and other tissue
GB2328443B (en) * 1997-08-21 2001-09-05 Reckitt & Colmann Prod Ltd In situ formation of pharmaceutically acceptable polymeric material
WO1999034751A1 (fr) 1998-01-06 1999-07-15 Sceusa Nicholas A Forme posologique de medicament reposant sur le gradient de teorell-meyer
JP4241985B2 (ja) * 1998-04-24 2009-03-18 株式会社クラレ 医療用接着材
US6200595B1 (en) 1998-04-24 2001-03-13 Kuraray Co., Ltd. Medical adhesive
JPH11318407A (ja) * 1998-05-19 1999-11-24 Lion Corp 加工食品
WO2000012144A1 (fr) 1998-08-31 2000-03-09 Coloplast A/S Composition susceptible d'absorber un fluide
JP4267106B2 (ja) * 1998-10-15 2009-05-27 株式会社クラレ 癒着防止用材料
JP4159682B2 (ja) * 1998-12-22 2008-10-01 株式会社クラレ 止血材
JP4149098B2 (ja) 1999-09-13 2008-09-10 株式会社クラレ 水膨潤性医療用高分子ゲルの製造法及び水膨潤性医療用高分子ゲル
US20030206958A1 (en) 2000-12-22 2003-11-06 Cattaneo Maurizio V. Chitosan biopolymer for the topical delivery of active agents
WO2003072157A1 (fr) * 2002-02-21 2003-09-04 Encelle, Inc. Matrices d'hydrogel bioactives immobilisees utilisees en tant que revetements de surface
US7217426B1 (en) * 2002-06-21 2007-05-15 Advanced Cardiovascular Systems, Inc. Coatings containing polycationic peptides for cardiovascular therapy
JP2004041586A (ja) 2002-07-15 2004-02-12 Fujimori Kogyo Co Ltd 生体適合性材料およびその製造方法
US7112713B2 (en) 2003-03-12 2006-09-26 Gelsus Research And Consulting, Inc. Dressing based on the Teorell-Meyer gradient
US7641643B2 (en) 2003-04-15 2010-01-05 Abbott Cardiovascular Systems Inc. Methods and compositions to treat myocardial conditions
EP1718147B1 (fr) * 2004-02-23 2012-03-28 Loma Linda University Medical Center Agent hemostatique a usage topique et interne
CA2559075A1 (fr) 2004-03-11 2005-09-22 Medtrade Products Limited Compositions d'alpha et beta chitosanes et leurs procedes de preparation
AU2005262070B2 (en) * 2004-07-09 2011-01-27 Ferrosan Medical Devices A/S Haemostatic composition comprising hyaluronic acid
BRPI0513572A (pt) * 2004-07-22 2008-05-06 Allan D Pronovost composições e métodos para tratamento de sangramento excessivo
JP2009513182A (ja) * 2005-07-21 2009-04-02 エフエムシー バイオポリマー エイエス 急速溶解する生体適合性被覆物で被覆した医療用部材
CA2628272A1 (fr) * 2005-11-02 2007-05-18 Aeris Therapeutics, Inc. Complexes de polycation-polyanion, compositions et procedes d'utilisation de ceux-ci
CN100411690C (zh) * 2006-01-17 2008-08-20 武汉理工大学 一种抑菌聚电解质多孔材料的制备方法
WO2007112446A2 (fr) 2006-03-28 2007-10-04 University Of Washington Nanofibres à base d'alginate et structures d'échafaudage associées
US20070237811A1 (en) * 2006-04-10 2007-10-11 Scherr George H Chitosan wound dressing
ITPD20060203A1 (it) 2006-05-22 2007-11-23 Univ Degli Studi Trieste Idrogeli di miscele di polisaccaridi per l'ingegneria tissutale e la veicolazione di composti attivi
CN1883721A (zh) * 2006-06-21 2006-12-27 哈尔滨工业大学 共价交联凝胶改性人工植入体的方法
US7935363B2 (en) * 2006-12-12 2011-05-03 Synthasome, Inc. Composite material for tissue repair
NZ599605A (en) 2007-02-19 2013-11-29 Marinepolymer Tech Inc Hemostatic compositions and therapeutic regimens
CA2691106C (fr) 2007-06-11 2014-11-18 National University Corporation Kyoto Institute Of Technology Procede de traitement d'equipement
US20090041858A1 (en) 2007-08-06 2009-02-12 Cao Group, Inc. Haemostatic Compositions Thickened by Polymers Containing Nitrogen Moieties
US20100291055A1 (en) * 2007-08-28 2010-11-18 Theodore Athanasiadis Surgical hydrogel
US20090123509A1 (en) 2007-11-08 2009-05-14 Cory Berkland Biodegradable Colloidal Gels as Moldable Tissue Engineering Scaffolds
US8283384B2 (en) * 2008-01-24 2012-10-09 University Of Utah Research Foundation Adhesive complex coacervates and methods of making and using thereof
WO2009132228A1 (fr) * 2008-04-24 2009-10-29 Medtronic, Inc. Composition protectrice contenant du chitosane
CN101463144B (zh) * 2009-01-12 2010-12-29 武汉理工大学 羟丙基壳聚糖/氧化海藻酸钠自交联抗菌水凝胶材料的制备方法
CN101463145A (zh) * 2009-01-12 2009-06-24 武汉理工大学 羧甲基壳聚糖/氧化海藻酸钠自交联抗菌水凝胶材料
EP2416741B1 (fr) 2009-04-06 2015-03-11 Bender Analytical Holding B.V. Systèmes d'alginate coagulant in situ
KR101103423B1 (ko) * 2009-09-04 2012-01-06 아주대학교산학협력단 생체 주입형 조직 접착성 하이드로젤 및 이의 생의학적 용도
CN102844053B (zh) 2009-11-25 2015-08-05 洛马林达大学医学中心 基于壳聚糖的止血织物
WO2011075557A1 (fr) * 2009-12-16 2011-06-23 The Trustees Of Columbia University In The City Of New York Procédés, dispositifs, et systèmes de délivrance de médicament à la demande déclenchée par ultrasons
US8389498B2 (en) 2010-03-26 2013-03-05 Taiwan Textile Research Institute Spinning solution and method for manufacturing biomaterial fibers
US8968362B2 (en) 2010-04-08 2015-03-03 Covidien Lp Coated looped suture
CN103025360A (zh) * 2010-05-24 2013-04-03 犹他大学研究基金会 增强的粘合剂复合物凝聚层和其制备和使用方法
CA2807012A1 (fr) * 2010-08-05 2012-02-09 Lifebond Ltd. Pansements et adhesifs contenant des compositions seches
CN102475691B (zh) 2010-11-30 2014-04-16 中国科学院大连化学物理研究所 海藻酸盐-壳聚糖酰基衍生物微胶囊及其制备和应用
US8911695B2 (en) 2011-03-17 2014-12-16 Perma-Fix Environmental Services, Inc. Preparation of chitosan-based microporous composite material and its applications
PL2626092T3 (pl) 2011-04-01 2016-02-29 Zhuhai Ortus Biotechnology Co Ltd Medyczny wchłanialny hemostatyczny materiał do ran z obnażeniem kości i sposób jego wytwarzania
GB2499359B (en) 2011-10-05 2016-12-28 Univ Of Bolton Polysaccharide fibres for wound dressings
CN109602944A (zh) 2011-11-13 2019-04-12 克里斯龙公司 原位可交联的聚合物组合物及其方法
EP2788038A1 (fr) 2011-12-09 2014-10-15 Acell, Inc. Dispositif hémostatique
AU2013356930B2 (en) 2012-12-10 2017-01-05 Regenics As Use of egg cellular extracts for skin rejuvenation
EP2983718A4 (fr) 2013-04-11 2016-12-07 Univ Of Vermont And State Agricultural College Décellularisation et recellularisation d'organes entiers
GB2554293B (en) 2015-06-11 2020-08-19 Murata Manufacturing Co Pump
MX2017016865A (es) 2015-06-22 2018-09-06 Cresilon Inc Andamio de polimero adhesivo hermostatico altamente eficaz.

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6150581A (en) * 1995-06-07 2000-11-21 United States Surgical Corporation Chitosan/alginate anti-adhesion barrier
US5836970A (en) * 1996-08-02 1998-11-17 The Kendall Company Hemostatic wound dressing
US20110144229A1 (en) * 2008-08-19 2011-06-16 The Regents Of The University Of Michigan Biocompatible coatings, and methods of making and using the same

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Gotah et al., Chemosphere, 2004, vol. 55, pages 135-140. *

Cited By (36)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9272069B2 (en) 2008-01-24 2016-03-01 University Of Utah Research Foundation Adhesive complex coacervates and methods of making and using thereof
US9913926B2 (en) 2008-01-24 2018-03-13 University Of Utah Research Foundation Adhesive complex coacervates and method of making and using thereof
US10517987B2 (en) 2008-01-24 2019-12-31 University Of Utah Research Foundation Adhesive complex coacervates and methods of making and using thereof
US9867899B2 (en) 2010-05-24 2018-01-16 University Of Utah Research Foundation Reinforced adhesive complex coacervates and methods of making and using thereof
US10653813B2 (en) 2010-05-24 2020-05-19 University Of Utah Research Foundation Reinforced adhesive complex coacervates and methods of making and using thereof
US9421300B2 (en) 2010-11-12 2016-08-23 University Of Utah Research Foundation Simple coacervates and methods of use thereof
US9173971B2 (en) 2010-11-12 2015-11-03 University Of Utah Research Foundation Simple adhesive coacervates and methods of making and using thereof
US9999700B1 (en) 2010-11-12 2018-06-19 University Of Utah Research Foundation Simple coacervates and methods of use thereof
US11383005B2 (en) 2011-11-13 2022-07-12 Cresilon, Inc. In-situ cross-linkable polymeric compositions and methods thereof
US10850003B2 (en) 2011-11-13 2020-12-01 Cresilon, Inc. In-situ cross-linkable polymeric compositions and methods thereof
US10077324B2 (en) 2013-02-06 2018-09-18 Kci Licensing, Inc. Polymers, preparation and use thereof
US10729579B2 (en) * 2014-07-11 2020-08-04 National Institutes Of Health Surgical tool and method for ocular tissue transplantation
US11723799B2 (en) 2014-07-11 2023-08-15 The United States Of America, As Represented By The Secretary, Department Of Health And Human Services Surgical tool and method for soft ocular tissue transplantation
US20170128263A1 (en) * 2014-07-11 2017-05-11 National Institutes Of Health Surgical tool and method for ocular tissue transplantation
US9913927B2 (en) 2014-07-14 2018-03-13 University Of Utah Research Foundation In situ solidifying complex coacervates and methods of making and using thereof
US10369249B2 (en) 2014-07-14 2019-08-06 University Of Utah Research Foundation In situ solidifying complex coacervates and methods of making and using thereof
US11471557B2 (en) 2014-07-14 2022-10-18 University Of Utah Research Foundation In situ solidifying solutions and methods of making and using thereof
US10729807B2 (en) 2014-07-14 2020-08-04 University Of Utah Research Foundation In situ solidifying solutions and methods of making and using thereof
KR102518121B1 (ko) * 2015-06-22 2023-04-05 크레실론, 인코퍼레이티드 고효율 지혈용 접착제 조성물 스캐폴드
WO2016209198A1 (fr) * 2015-06-22 2016-12-29 Cresilion, Inc. Échafaudage polymère adhésif hémostatique hautement efficace
AU2015399459B2 (en) * 2015-06-22 2021-02-18 Cresilon, Inc. Highly efficacious hemostatic adhesive polymer scaffold
RU2750648C2 (ru) * 2015-06-22 2021-06-30 Кресилон, Инк. Высокоэффективный гемостатический адгезивный полимерный каркас
CN115463248A (zh) * 2015-06-22 2022-12-13 克里斯伦公司 高度有效的止血粘附性聚合物支架
KR20180053636A (ko) * 2015-06-22 2018-05-23 크레실론, 인코퍼레이티드 고효율 지혈용 접착제 조성물 스캐폴드
US10660945B2 (en) 2015-08-07 2020-05-26 Victor Matthew Phillips Flowable hemostatic gel composition and its methods of use
US10751444B2 (en) 2015-08-07 2020-08-25 Victor Matthew Phillips Flowable hemostatic gel composition and its methods of use
US11065337B2 (en) 2015-12-14 2021-07-20 University of Pittsburgh—of the Commonwealth System of Higher Education Complex coacervate for controlled release and related methods
US11779647B2 (en) 2015-12-14 2023-10-10 University of Pittsburgh—of the Commonwealth System of Higher Education Complex coacervate for controlled release and related methods
US11298423B2 (en) * 2016-03-04 2022-04-12 University of Pittsburgh—of the Commonwealth System of Higher Education Protection and delivery of multiple therapeutic proteins
US11857631B2 (en) 2016-03-04 2024-01-02 University of Pittsburgh—of the Commonwealth System of Higher Education Protection and delivery of multiple therapeutic proteins
US11266678B2 (en) * 2016-08-25 2022-03-08 Pharmaresearch Co., Ltd. Composition for articular cavity injection comprising nucleic acid and chitosan
WO2018119320A1 (fr) * 2016-12-21 2018-06-28 Cresilon, Inc. Compositions hémostatiques comprenant des agents antifibrinolytiques
US11541151B2 (en) 2017-09-20 2023-01-03 Cha University Industry-Academic Cooperation Foundation Coacervate composition containing protein drug and wound healing agent comprising same
US20190328933A1 (en) * 2018-01-26 2019-10-31 Polarityte, Inc. Composite-interfacing biomaterial accelerant substrate
US11896234B2 (en) 2018-01-26 2024-02-13 Fluidx Medical Technology, Llc Apparatus and method of using in situ solidifying complex coacervates for vascular occlusion
US12016968B2 (en) 2020-12-23 2024-06-25 Cresilon, Inc. Highly efficacious hemostatic adhesive polymer scaffold

Also Published As

Publication number Publication date
ZA201403166B (en) 2015-11-25
CA2855347C (fr) 2019-03-05
CA2855347A1 (fr) 2013-05-16
JP2014533181A (ja) 2014-12-11
RU2014124157A (ru) 2015-12-27
US9687584B1 (en) 2017-06-27
MX366366B (es) 2019-07-05
IN2014CN03524A (fr) 2015-10-09
MX2014005738A (es) 2014-07-09
RU2017144044A (ru) 2019-02-15
US20170266339A1 (en) 2017-09-21
IL232330B (en) 2019-06-30
CN109602944A (zh) 2019-04-12
KR20140090670A (ko) 2014-07-17
HK1201734A1 (en) 2015-09-11
WO2013071235A9 (fr) 2013-07-18
EP2776068A4 (fr) 2015-05-20
US20170157286A1 (en) 2017-06-08
JP2018183611A (ja) 2018-11-22
SG11201402279SA (en) 2014-06-27
EP2776068A1 (fr) 2014-09-17
IL232330A0 (en) 2014-06-30
MX2019008051A (es) 2019-09-09
US10850003B2 (en) 2020-12-01
RU2640084C2 (ru) 2017-12-26
US11383005B2 (en) 2022-07-12
AU2017219007A1 (en) 2017-09-07
CN103930133A (zh) 2014-07-16
SG10201610469QA (en) 2017-02-27
WO2013071235A1 (fr) 2013-05-16
BR112014011442A8 (pt) 2018-01-09
AU2012334982A1 (en) 2014-05-22
US20210290817A1 (en) 2021-09-23
JP7013336B2 (ja) 2022-01-31
JP2021007754A (ja) 2021-01-28
BR112014011442A2 (pt) 2017-05-16

Similar Documents

Publication Publication Date Title
US11383005B2 (en) In-situ cross-linkable polymeric compositions and methods thereof
Shah et al. Biopolymer-based biomaterials for accelerated diabetic wound healing: A critical review
Laurano et al. Wound dressing products: A translational investigation from the bench to the market
Kamoun et al. A review on polymeric hydrogel membranes for wound dressing applications: PVA-based hydrogel dressings
Kurakula et al. Alginate-based hydrogel systems for drug releasing in wound healing
Moura et al. Recent advances on the development of wound dressings for diabetic foot ulcer treatment—A review
Ji et al. Advances in chitosan-based wound dressings: Modifications, fabrications, applications and prospects
Sheokand et al. Natural polymers used in the dressing materials for wound healing: Past, present and future
Mercy et al. Chitosan-derivatives as hemostatic agents: Their role in tissue regeneration
Ghadi et al. Microparticulate polymers and hydrogels for wound healing
Zahra et al. Exploring the recent developments of alginate silk fibroin material for hydrogel wound dressing: a review
Gokarneshan Application of natural polymers and herbal extracts in wound management
Yaşayan et al. Natural polymers for wound dressing applications
Shi et al. Recent progresses of collagen dressings for chronic skin wound healing
Davis et al. Passive and interactive dressing materials
Yang et al. Effect of natural polymer materials on skin healing based on internal wound microenvironment: a review
Pal Kaur et al. Material couture for wound healing and regeneration: an overview
Islam et al. Chitosan and chitosan-based biomaterials for wound management
Khalid et al. Polysaccharide composites as a wound-healing sponge
NZ723969B2 (en) In-situ cross-linkable polymeric compositions and methods thereof
NZ723969A (en) In-situ cross-linkable polymeric compositions and methods thereof
Wahid Polysaccharide Composites as a Wound-Healing Sponge
Kebria et al. Polymers in wound repair and skin regeneration
Zhang et al. Advances of biological macromolecules hemostatic materials: A review
Li et al. Application of Hydrogel in Skin Repair

Legal Events

Date Code Title Description
AS Assignment

Owner name: SUNERIS, INC., NEW YORK

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:LANDOLINA, JOSEPH A.;REEL/FRAME:032861/0768

Effective date: 20140508

Owner name: SUNERIS, INC., NEW YORK

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:LANDOLINA, JOSEPH A;REEL/FRAME:032861/0443

Effective date: 20140508

AS Assignment

Owner name: CRESILON, INC., NEW YORK

Free format text: CHANGE OF NAME;ASSIGNOR:SUNERIS, INC.;REEL/FRAME:040029/0696

Effective date: 20160816

Owner name: CRESILON, INC., NEW YORK

Free format text: CHANGE OF NAME;ASSIGNOR:SUNERIS, INC.;REEL/FRAME:040029/0810

Effective date: 20160816

STCB Information on status: application discontinuation

Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION