New! View global litigation for patent families

US3911116A - Process for promoting wound healing with chitin derivatives - Google Patents

Process for promoting wound healing with chitin derivatives Download PDF

Info

Publication number
US3911116A
US3911116A US38071173A US3911116A US 3911116 A US3911116 A US 3911116A US 38071173 A US38071173 A US 38071173A US 3911116 A US3911116 A US 3911116A
Authority
US
Grant status
Grant
Patent type
Prior art keywords
chitin
healing
wound
alkyl
material
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.)
Expired - Lifetime
Application number
Inventor
Leslie L Balassa
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.)
Lescarden Ltd
Original Assignee
Leslie L Balassa
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
Grant date

Links

Images

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/70Carbohydrates; Sugars; Derivatives thereof
    • A61K31/715Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08BPOLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/0006Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
    • C08B37/0024Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Glucans; (beta-1,3)-D-Glucans, e.g. paramylon, coriolan, sclerotan, pachyman, callose, scleroglucan, schizophyllan, laminaran, lentinan or curdlan; (beta-1,6)-D-Glucans, e.g. pustulan; (beta-1,4)-D-Glucans; (beta-1,3)(beta-1,4)-D-Glucans, e.g. lichenan; Derivatives thereof
    • C08B37/00272-Acetamido-2-deoxy-beta-glucans; Derivatives thereof
    • C08B37/003Chitin, i.e. 2-acetamido-2-deoxy-(beta-1,4)-D-glucan or N-acetyl-beta-1,4-D-glucosamine; Chitosan, i.e. deacetylated product of chitin or (beta-1,4)-D-glucosamine; Derivatives thereof

Abstract

Wound healing compositions and the process of healing wounds with such compositions are described, the compositions containing a chitin derivative.

Description

United States Patent [191 Balassa [451 *Oct.7, 1975 PROCESS FOR PROMOTING WOUND HEALING WITH CHITIN DERIVATIVES [76] Inventor: Leslie L. Balassa, Tomahawk Lake,

Blooming Grove, N.Y. 10914 The portion of the term of this patent subsequent to Jan. 4, 1989, has been disclaimed.

22 Filed: July 19,1973

211 App1.No.:380,711

Related US. Application Data [63] Continuation of Ser. No. 27,977, April 13, 1970, abandoned, which is a continuation-in-part of Ser. Nos. 619,007, Feb. 27, 1967, abandoned, which is a continuation of Ser. No. 704,538, Feb. 12, 1968, Pat. No. 3,632,754.

[ Notice:

[52] US. Cl. 424/180; 424/28; 424/95 ['51] Int. Cl. A6lK 31/70 Carlozzi et al..... 424/180 Weisberg et a]. 424/330 Primary ExaminerStanley J. Friedman Assistant Examiner-Daren M. Stephens Attorney, Agent, or FirmDarby & Darby 5 7 ABSTRACT Wound healing compositions and the process of healing wounds with such compositions are described, the compositions containing a chitin derivative.

4 Claims, N0 Drawings PROCESS FOR PROMOTING WOUND HEALING WITH CHITIN DERIVATIVES This is a continuation of application Ser. No. 27,977, filed Apr. 13, 1970 and now abandoned, which in turn is a continuation-in-part of my copending application Ser. No. 619,007 filed Feb. 27, 1967, now abandoned, and a continuation of application Ser. No. 704,538 filed Feb. 12, 1968, now US. Pat. No. 3,632,754.

This invention relates to methods of promoting the healing of wounds and compositions therefor comprising chitin derivatives.

Medicinehas long been interested in improving the healing of wounds. Patients suffering from diabetes or undergoing extensive cortisone treatment show extremely slow rates of healing of any wounds which they receive. Thus, surgery on such patients involves additional risks not present with other patients. Moreover, rapid healing of wounds is particularly desired for patients in tropical countries where the risk of infection is high. Rapid healing is also desired in the case of so]- diers who have been wounded in a battle zone and cannot easily and quickly be removed therefrom. Acceleration of wound healing is highly desirable in the case of patients who cannot readily be immobilized, such as farm animals.

In evaluating the utility of a material to promote wound healing, a reproducible test is necessary to give comparative data. Such a test method has been described by Prudden et al in: The Acceleration of Wound Healing with Cartilage, Surgery, Gynecology and Obstetrics, 1052283 1957). In this method, rats are tested in pairs, each pair receiving an identical surgical incision, only the one rat of the pair receiving a measured dose of the material whose wound healing properties is to be determined. The pair is then kept in the same cage and the tensile strength of the wounds in the two rats is determined in millimeters of mercury. The difference in the tensile strengths between the treated rat and the control rat is expressed as the percentage improvement obtained. Considering biological variance it is believed that only differences of about or more are significant.

There have been several recent developments reported concerning materials which promote wound healing. In this connection US. Pat. No. 3,232,836 describes the parenteral administration of N- acetylglucosamine as a wound healing material. Utilizing the test method of Prudden et a1 referred to in the preceding paragraph, N-acetylglucosamine showed improvement in tensile strength of only about 10% whereasPrudden and his co-workers have reported significantly larger increases in wound healing by the use of cartilage preparations from various animals. Depending on the age and species of animal and the fineness of the cartilage powder, improvements ranging from to 40% in wound healing tensile strength have been reported by Prudden.

Now it has been discovered that finely divided chitin, partially depolymerized chitin, and chitin derivatives possess the ability to promote the healing of wounds.

Accordingly, one aspect of the present invention relates to novel methods of promoting and assisting the healing of wounds as, for example, damaged mammalian tissue, open ulcers, etc., and to compositions therefor.

Another aspect of the invention relates to significant improvements in wound healing strength achieved by the administration of finely divided chitin, partially depolymerized chitin or chitin derivatives to a patient.

An additional aspect of the present invention is concerned with articles of manufacture such as surgical bandages, surgical sutures, etc., containing the wound healing materials of the present invention.

These and other aspects of the present invention will be apparent from the following description.

Chitin is a polysaccharide, believed to be poly (N- acetylglucosamine) which forms the cell walls of fungi and the hard shell of insects and crustaceans. As used herein, the term chitin embraces naturally occurring chitin, synthetic chitin, as well as poly (N- acetylglucosamine) and its epimer poly (N- acetylgalactosamine). The partially depolymerized chitin, e.g. chitotriose, chitobiose, is a substance which retains its polymeric nature but has undergone a reduction in molecular weight (i.e., chain length) as a result of (l enzymatic action such as by a chitinase enzyme, (2) chemical treatment such as acid hydrolysis or alkaline treatment, and (3) physical treatment.

The chitin derivatives contemplated are materials such as ethers formed with pharmaceutically acceptable radicals and esters or salts with pharmaceutically acceptable acids. Examples of suitable derivatives include hydroxy lower alkyl chitin such as hydroxyethyl chitin, carboxy alkyl chitin such as carboxymethyl chitin, salts of carboxy lower alkyl chitin such as the zinc salt, lower alkyl chitin such as methyl chitin and ethyl chitin, chitin acetate, chitin nitrate, chitin citrate, chitin-phosphate, N-acyl derivatives derived from monocarboxylic aliphatic acids such as N-formyl, N-acetyl, N-prop'ionyl, N-caproyl, etc.

It is preferred to use natural chitin as the wound healing accelerator. The naturally occurring chitin is preferably chitin of fungal origin, both by reason of its ready availability and its high degree of effectiveness.

The degree of improvement in wound healing obtained with the chitin materials is at least equal to and in many instances greater than that derived from the cartilage materials of the prior art. The substantial improvement in rate of healing which is obtained from the use of poly( N-acetylglucosamine), i.e., chitin, as compared to monomeric N-acetylglucosamine is particularly surprising. As compared to the great variability in cartilage depending on the animal, its age and the method of collecting the cartilage, chitin, particularly chitin of fungal origin, is a relatively uniform and easily obtained material.

The compositions of the present invention are applied using the same techniques and processes developed for cartilage, and N-acetylglucosamine. Thus, it is preferred to topically apply finely divided chitin directly to the wound surface. However, tablets, capsules or pellets of chitin may be prepared from mixtures of chitin, partially depolymerized chitin or chitin derivatives with well-known pharmaceutical excipients such as starch, sugar, certain forms of clay, etc. Such tablets, capsules or pellets may be taken orally or implanted near the situs of the wound. Alternatively, a colloidal solution may be prepared from chitin, preferably in isotonic saline, or a water-soluble derivative of chitin may be dissolved preferably in isotonic saline solution, and the solution administered intramuscularly, parenterally or intravenously.

A powder or solution of chitin or of a chitin derivative may also be used to impregnate a surgical gauze or pad which is applied to the wound. Chitin may also be dissolved as the alkali chitin xanthate, spun into fibers and regenerated as the virtually undegraded polymer in accordance with the procedures described in the prior art by Thor et al. Partially deacetylated chitin filaments and fibers may be prepared in accordance with the procedure described in US. Pat. No. 2,040,880. These chitin fibers may then be used as surgical sutures or included in bandages or other support base for surgical dressings either in a woven or nonwoven fabric structure in the manner described in U.S. Pat. No. 3,196,075. Chitin or chitin derivative may also be made up into an ointment or salve. The use of nonactive carriers for the chitin is not preferred as the presence of extraneous matter in a wound frequently tends to interfere with the healing process due to the interposition effect.

As previously stated, where the chitin is to be applied by injection, i.e., either intramuscularly, parenterally or intravenously, it is first necessary to prepare a dispersion or a solution of the material in a pharmaceutically acceptable liquid. Colloidal solutions of chitin may be prepared using the method described by Lingappa and Lockwood in NATURE, 189, page 158 (1961). When administered intravenously it is preferred to administer the compound in isotonic solution such as isotonic saline.

The chitin or chitin derivatives may be used alone, in admixture with each other, with cartilage, or may be co-administered with other therapeutically effective agents such as ascorbic acid, ascorbyl palmitate, pharmaceutically acceptable zinc salts such as zinc oxide, zinc ascorbate, zinc sulfate and zinc stearate; antiseptics such as thimerosal and benzalkonium chloride; local anesthetics such as lidocaine and procaine; antibiotics such as chloramphenicol, sulfanilamide and ampicilline. Combinations of the therapeutically effective agents described above with chitin and/or chitin derivatives may be used.

Suitable sources of chitin are from lobsters, shrimp and other crustacea. To utilize chitin from such sources, it is necessary to reduce the chitin in particle size to less than about 150 microns and preferably less than about 50 microns. Due to the tough and rather fi brous nature of chitin from such sources, this grinding is diffieult and expensive. Accordingly, it is preferred to use chitin of fungal origin. The cell walls of fungi are made of chitin. It has been found that it is not necessary to extract the chitin from the remaining cell material. Thus, if desired, after suitable sterilization as by heat or gas (i.e., ethylene oxide), the entire fungal mat produced by fermentation of a fungus in a suitable nutrient medium may be ground and used to promote healing of wounds. Preferably, however, the fungal mat is treated to remove the extraneous materials leaving only the chitin skeletons. Purifying the material in this manner eliminates the nonchitinous materials, thus substantially reducing the possibility of an allergic reaction and eliminating any interference with the healing process which might be caused by such materials.

Finely divided chitin or chitin derivatives may be applied topically by blowing a metered amount of the material onto the wound using a hand atomizer. Alternatively, it may be applied by dusting as from a hand shaker or may be placed together with an inert gas under increased pressure (i.e., above atmospheric pressure) in a pressure vessel. In this latter means of application, termed aerosol application, the finely divided chitin or chitin derivative, optionally with other medicaments as indicated, may be packaged as a dry aerosol powder as described in Dutch patent application No. 6,415,252, published July 5, 1965 (this patent application is directed to a medicament for bovine mastitis but the method of aerosol packaging described is applicable to powdered medicament having the described particle size) or as an aerosol foam.

1n the following examples, the wound healing efficiency of the various chitinous materials is determined by using the method of Prudden et al as described above. In general, at least 10 pairs of rats are used to obtain a meaningful average for each material tested. In each of these examples a powder insufflator is used to apply 2 to 10 mg./cm of wound surface of the material tested. I

EXAMPLE 1 Commercial lobster shell chitin is ground to a fine powder in a laboratory 4-quart size porcelain jar mill loaded with l-inch size (average) flint pebbles in a weight ratio of l chitin to 2 pebbles. Dry ice is then put on top of the mill charge and the mill is kept open for 5 minutes to allow the CO to displace the air in the mill. The lid of the mill is then clamped on tight and the grinding carried out for 96 hours. Approximately 50% of the powdered chitin passed through a 40 micron screen.

The whole powdered chitin so produced is then applied to the 45 test rats of 45 pairs of rats used in the Prudden et al assay method described above. The percent of wound healing for the treated rats, stating the control rats as 100%, is 122%, Le, the use of chitin results in an average 22% increase in wound healing activity.

EXAMPLES 2-5 Various fungi are grown on either brain-heart infusion (200 gm. calf brain, 250 gm. beef heart, 10 gm. proteose peptone, 2 gm. dextrose, 5 gm. sodium chloride and 2.5 gm. disodium phosphate) called BHI or on Sabourauds broth (40 gm. dextrose and 10 gm. bactopeptone) called SAB. The cultures are grown in shallow layers of media contained in flasks and held stationary'until good growth and extensive sporulation occurs. Prior to collection of the growth mats, the cultures are killed by placing the flasks into a closed oven under CO at 127C. for 3 hours. The flasks are then cooled in the oven for an additional 1 hour and 15 minutes. Culture broths are removed by filtration through Buchner funnels and the growth mats washed with distilled water. The mats are then frozen and lyophilized and the dry products ground in a mortar with a pestle under CO No attempt is made to purify the chitin. Twelve pairs of rats are used for each test. Some inflammation is observed on all treated wounds and infection on several. The increases in wound healing obtained may be all the more significant in view of those adverse factors.

"/1 Wound Healing (Control "/2 improve Example Fungus Me- 100) ment dium 2 Mucor spinosus SAB 136 36 3 Aspergillus niger BHl 1 l8 l8 4 Penieillium RH! 146 46 5 Cryptococcus RH! 128 28 EXAMPLE 6 100 grams of dried fungus material (obtained from Penicillium fungus of Example 4, cultured on a BHI medium, sterilized by boiling the fungus with the medium and then filtering, washing with distilled water and drying the fungus material) is defatted by extracting the solvent-soluble fatty materials with 1,000 ml. chloroform at room temperature. The chloroform is removed by filtering and then drying at reduced pressure in a vacuum desiccator.

The defatted fungus material is treated with 2,000 ml. 1.0 N NaOH solution for 18 hours at room temperature. The material is then acidified with HCl. Thereafter the material is dialyzed in distilled water until the wash water is free from chlorine ions. This procedure is repeated until a substantially purified material is obtained. The material is dried in vacuum below 50C and is a gray, friable mass.

The dried materialis ground in a laboratory mortar and screened through a 400 mesh standard screen. When the screened material is applied to 20 test rats of 20 pairs of rats there is obtained an average of about increase in the wound healing of the treated rats over the untreated control rats.

EXAMPLE 7 Lobster shell chitin is purified by first slurrying it in 10% aqueous NaOH for 5 minutes at 80C, then it is washed, drained and slurried in 10% HCl for 5 minutes at C, drained, slurried in water, the pH of the water adjusted to 6 with dilute aqueous NaOH and finally drained and dried.

The dried chitin material is pulverized to a fineness of about 40 microns. The material shows an average 25% increase in the wound healing over the untreated control rats.

Although the present invention has been described in conjunction with preferred embodiments, it is to be understood that modifications and variations may be resorted to without departing from the spirit and scope thereof, as those skilled in the art will readily understand.

What is claimed is:

l. A process for facilitating healing of a wound in a mammal which comprises topically administering a therapeutically effective dosage of a material selected from the group consisting of hydroxy lower alkyl chitin, carboxy lower alkyl chitin, lower alkyl chitin, chitin acetate, chitin phosphate, chitin nitrate, a salt of carboxy lower alkyl chitin and chitin citrate.

2. A process for accelerating the healing of a surgical wound in a mammal requiring healing which comprises administering to said wound a therapeutically effective dosage of a finely divided material selected from the group consisting of hydroxy lower alkyl chitin, carboxy lower alkyl chitin, lower alkyl chitin, chitin acetate, chitin phosphate, chitin nitrate, a salt of carboxy lower alkyl chitin and chitin citrate.

3. A process for facilitating healing of a wound in a mammal which comprises parenterally administering a therapeutically effective dosage of a material selected from the group consisting of hydroxy lower alkyl chitin, carboxy lower alkyl chitin, lower alkyl chitin, chitin acetate, chitin phosphate, chitin nitrate, a salt of carboxy lower alkyl chitin and chitin citrate.

4. A process according to claim 2 which comprises topically administering said finely divided material at the site of said wound.

Claims (4)

1. A PROCESS FOR FACILITATING HEALING OF A WOUND IN A MAMMAL WHICH COMPRISES TOPICALLY ADMINISTERING A THEREAPEUTICALLY EFFECTIVE DOSAGE OF A MATERIAL SELECTED FROM THE GROUP CONSISTING OF HYDROXY LOWER ALKYL CHITIN, CARBOXY LOWER ALKYL CHITIN, LOWER ALKYL CHITIN, CHITIN ACETATE, CHITIN PHOSPHATE, CHITIN NITRATE, A SALT OF CARBOXY LOWER ALKYL CHITIN AND CHITIN CITRATE.
2. A process for accelerating the healing of a surgical wound in a mammal requiring healing which comprises administering to said wound a therapeutically effective dosage of a finely divided material selected from the group consisting of hydroxy lower alkyl chitin, carboxy lower alkyl chitin, lower alkyl chitin, chitin acetate, chitin phosphate, chitin nitrate, a salt of carboxy lower alkyl chitin and chitin citrate.
3. A process for facilitating healing of a wound in a mammal which comprises parenterally administering a therapeutically effective dosage of a material selected from the group consisting of hydroxy lower alkyl chitin, carboxy lower alkyl chitin, lower alkyl chitin, chitin acetate, chitin phosphate, chitin nitrate, a salt of carboxy lower alkyl chitin and chitin citrate.
4. A process according to claim 2 which comprises topically administering said finely divided material at the site of said wound.
US3911116A 1970-04-13 1973-07-19 Process for promoting wound healing with chitin derivatives Expired - Lifetime US3911116A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US2797770 true 1970-04-13 1970-04-13
US3911116A US3911116A (en) 1970-04-13 1973-07-19 Process for promoting wound healing with chitin derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US3911116A US3911116A (en) 1970-04-13 1973-07-19 Process for promoting wound healing with chitin derivatives

Publications (1)

Publication Number Publication Date
US3911116A true US3911116A (en) 1975-10-07

Family

ID=26703102

Family Applications (1)

Application Number Title Priority Date Filing Date
US3911116A Expired - Lifetime US3911116A (en) 1970-04-13 1973-07-19 Process for promoting wound healing with chitin derivatives

Country Status (1)

Country Link
US (1) US3911116A (en)

Cited By (50)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4035267A (en) * 1976-08-30 1977-07-12 American Cyanamid Company Dry shampoo using chitin powder
US4059097A (en) * 1976-11-03 1977-11-22 American Cyanamid Company Method of minimizing tissue reaction during surgery with chitin
US4064564A (en) * 1976-11-03 1977-12-27 American Cyanamid Company Chitin derived surgical glove powder
US4068757A (en) * 1976-11-03 1978-01-17 American Cyanamid Company Chitin derived powder in sterile surgical element package
US4086335A (en) * 1975-10-29 1978-04-25 Bruscato Frank N Pharmaceutical tablets containing chitin as a disintegrant
US4394373A (en) * 1981-04-06 1983-07-19 Malette William Graham Method of achieving hemostasis
US4452785A (en) * 1982-11-08 1984-06-05 Malette William Graham Method for the therapeutic occlusion
US4486416A (en) * 1981-03-02 1984-12-04 Soll David B Protection of human and animal cells subject to exposure to trauma
US4532134A (en) * 1981-04-06 1985-07-30 Malette William Graham Method of achieving hemostasis, inhibiting fibroplasia, and promoting tissue regeneration in a tissue wound
US4572906A (en) * 1983-11-21 1986-02-25 Her Majesty The Queen In Right Of Canada, As Represented By The Minister Of National Defence Of Her Majesty's Canadian Government Chitosan based wound dressing materials
WO1986005789A1 (en) * 1985-04-01 1986-10-09 Biocarb Ab Carbohydrate derivatives and compositions thereof for therapeutic or diagnostic use, and methods for their use
US4645757A (en) * 1979-06-21 1987-02-24 Landstingens Inkopscentral Lic Ekonomisk Forening Agent for preventing or treating infections in human beings and animals
US4920158A (en) * 1989-10-11 1990-04-24 Medipro Sciences Limited Hydrogel-forming wound dressing or skin coating material
WO1990006124A1 (en) * 1988-12-07 1990-06-14 Bentech Laboratories, Inc. Formulations for treating slow and non-healing wounds
US5013769A (en) * 1988-08-22 1991-05-07 Medipro Sciences Limited Method of making a hydrogel-forming wound dressing or skin coating material
US5021207A (en) * 1986-12-16 1991-06-04 E. I. Du Pont De Nemours And Company High strength fibers from chitin derivatives
US5197945A (en) * 1988-05-31 1993-03-30 Minnesota Mining And Manufacturing Company Alginate wound dressing of good integrity
US5733884A (en) * 1995-11-07 1998-03-31 Nestec Ltd. Enteral formulation designed for optimized wound healing
US6117851A (en) * 1996-12-13 2000-09-12 Lescarden Inc. Treatment of osteoarthritis by administering poly-N-acetyl-D-glucosamine
US6150581A (en) * 1995-06-07 2000-11-21 United States Surgical Corporation Chitosan/alginate anti-adhesion barrier
US6444797B1 (en) 2000-07-18 2002-09-03 Ibeks Technologies Co., Ltd. Chitosan microflake and method of manufacturing the same
US20030148998A1 (en) * 2001-02-16 2003-08-07 Cargill, Incorporated Glucosamine and method of making glucosamine from microbial biomass
US20030206958A1 (en) * 2000-12-22 2003-11-06 Cattaneo Maurizio V. Chitosan biopolymer for the topical delivery of active agents
US6693188B2 (en) 2001-08-08 2004-02-17 Cargill Incorporated N-acetyl-D-glucosamine and process for producing N-acetyl-D-glucosamine
US20040077055A1 (en) * 2001-02-16 2004-04-22 Cargill, Incorporated Glucosamine and method of making glucosamine from microbial biomass
US20040243043A1 (en) * 2002-06-14 2004-12-02 Mccarthy Simon J, Wound dressing and method for controlling severe, life-threatening bleeding
US20050038369A1 (en) * 2001-06-14 2005-02-17 Gregory Kenton W. Wound dressing and method for controlling severe, life-threatening bleeding
US20050215774A1 (en) * 2002-04-02 2005-09-29 Trinkle Jamea R Chitosan production
US20050245482A1 (en) * 2000-03-15 2005-11-03 Weiyu Fan Chitosan and method of preparing chitosan
EP1607406A1 (en) 2004-06-18 2005-12-21 Taiwan Hopax Chems. Mfg. Co., Ltd Chemically modified polyaminosaccharide by a hydrocarbyl sultone compound
US20050281886A1 (en) * 2004-05-06 2005-12-22 Ivrea Pharmaceuticals, Inc. Particles for the delivery of active agents
US20060004314A1 (en) * 2001-06-14 2006-01-05 Hemcon, Inc. Antimicrobial barriers, systems, and methods formed from hydrophilic polymer structures such as chistosan
US20060003965A1 (en) * 2002-11-01 2006-01-05 Fosdick Lawrence D N-acetyl-d-glucosamine (nag) supplemented food products and beverages
US20060058263A1 (en) * 2002-11-01 2006-03-16 Rogers Brent D Heat pasturized liquids containing glucosamine
US20060141046A1 (en) * 2004-05-06 2006-06-29 Ivrea Pharmaceuticals, Inc. Particles for the delivery of active agents
US20060172392A1 (en) * 2001-02-16 2006-08-03 Cargill, Incorporated Water soluble beta-glucan, glucosamine, and N-acetylglucosamine compositions and methods for making the same
US20060178344A1 (en) * 2001-02-16 2006-08-10 Cargill, Incorporated Glucosamine and N-acetylglucosamine and methods of making the same fungal biomass
US20060211973A1 (en) * 2005-03-17 2006-09-21 Gregory Kenton W Systems and methods for hemorrhage control and or tissue repair
US20060246114A1 (en) * 2002-11-01 2006-11-02 Rogers Brent D Multiple component food product useful for delivering glucosamine and/or nacetyl-d-glucosamine
US20080146984A1 (en) * 2002-06-14 2008-06-19 Hemcon Medical Technologies, Inc. Method for preparing a compressed wound dressing
US20080287907A1 (en) * 2006-05-23 2008-11-20 Providence Health System-Oregan D/B/A Providence St. Vincent Medical Center Systems and methods for introducing and applying a bandage structure within a body lumen or hollow body organ
US20090018479A1 (en) * 2002-06-14 2009-01-15 Hemcon Medical Technologies, Inc. Absorbable tissue dressing assemblies, systems, and methods formed from hydrophilic polymer sponge structures such as chistosan
US20090104284A1 (en) * 2007-10-19 2009-04-23 Gunn Jr Herbert Harrell Topically Applied Chitosan Composition for Pain Relief and Boosting Immune System
US20100172958A1 (en) * 2008-05-02 2010-07-08 Hemcon Medical Technologies, Inc. Wound dressing devices and methods
US20100228185A1 (en) * 2008-12-22 2010-09-09 Abbott Laboratories Carriers for hemostatic tract treatment
US20100323986A1 (en) * 2001-02-12 2010-12-23 Marine Polymer Technologies, Inc., Compositions and methods for modulation of vascular structure and/or function
US20110237539A1 (en) * 2010-03-26 2011-09-29 Taiwan Textile Research Institute Spinning Solution and Method for Manufacturing Biomaterial Fibers
US8715719B2 (en) 2010-06-16 2014-05-06 Abbott Vascular, Inc. Stable chitosan hemostatic implant and methods of manufacture
US8741335B2 (en) 2002-06-14 2014-06-03 Hemcon Medical Technologies, Inc. Hemostatic compositions, assemblies, systems, and methods employing particulate hemostatic agents formed from hydrophilic polymer foam such as Chitosan
US8992453B2 (en) 2003-09-12 2015-03-31 Marine Polymer Technologies, Inc. Vascular access preservation in hemodialysis patients

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2040879A (en) * 1934-06-21 1936-05-19 Du Pont Substantially undegraded deacetylated chitin and process for producing the same
US2795579A (en) * 1953-10-09 1957-06-11 Warner Lambert Pharmaceutical Process for purification of chitosan by means of the salicylic acid salt thereof
US3232836A (en) * 1959-08-24 1966-02-01 Pfizer & Co C Facilitating healing of body surface wounds by intravenous administration of n-acetyl glucosamine, glucosamine, or pharmaceutically acceptable acid salts of glucosamine
US3257275A (en) * 1962-02-07 1966-06-21 Weisberg Mark Chitosan containing antacid composition and method of using same

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2040879A (en) * 1934-06-21 1936-05-19 Du Pont Substantially undegraded deacetylated chitin and process for producing the same
US2795579A (en) * 1953-10-09 1957-06-11 Warner Lambert Pharmaceutical Process for purification of chitosan by means of the salicylic acid salt thereof
US3232836A (en) * 1959-08-24 1966-02-01 Pfizer & Co C Facilitating healing of body surface wounds by intravenous administration of n-acetyl glucosamine, glucosamine, or pharmaceutically acceptable acid salts of glucosamine
US3257275A (en) * 1962-02-07 1966-06-21 Weisberg Mark Chitosan containing antacid composition and method of using same

Cited By (81)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4086335A (en) * 1975-10-29 1978-04-25 Bruscato Frank N Pharmaceutical tablets containing chitin as a disintegrant
US4035267A (en) * 1976-08-30 1977-07-12 American Cyanamid Company Dry shampoo using chitin powder
US4059097A (en) * 1976-11-03 1977-11-22 American Cyanamid Company Method of minimizing tissue reaction during surgery with chitin
US4064564A (en) * 1976-11-03 1977-12-27 American Cyanamid Company Chitin derived surgical glove powder
US4068757A (en) * 1976-11-03 1978-01-17 American Cyanamid Company Chitin derived powder in sterile surgical element package
US4645757A (en) * 1979-06-21 1987-02-24 Landstingens Inkopscentral Lic Ekonomisk Forening Agent for preventing or treating infections in human beings and animals
US4486416A (en) * 1981-03-02 1984-12-04 Soll David B Protection of human and animal cells subject to exposure to trauma
US4532134A (en) * 1981-04-06 1985-07-30 Malette William Graham Method of achieving hemostasis, inhibiting fibroplasia, and promoting tissue regeneration in a tissue wound
US4394373A (en) * 1981-04-06 1983-07-19 Malette William Graham Method of achieving hemostasis
US4452785A (en) * 1982-11-08 1984-06-05 Malette William Graham Method for the therapeutic occlusion
US4572906A (en) * 1983-11-21 1986-02-25 Her Majesty The Queen In Right Of Canada, As Represented By The Minister Of National Defence Of Her Majesty's Canadian Government Chitosan based wound dressing materials
WO1986005789A1 (en) * 1985-04-01 1986-10-09 Biocarb Ab Carbohydrate derivatives and compositions thereof for therapeutic or diagnostic use, and methods for their use
US5021207A (en) * 1986-12-16 1991-06-04 E. I. Du Pont De Nemours And Company High strength fibers from chitin derivatives
US5197945A (en) * 1988-05-31 1993-03-30 Minnesota Mining And Manufacturing Company Alginate wound dressing of good integrity
US5013769A (en) * 1988-08-22 1991-05-07 Medipro Sciences Limited Method of making a hydrogel-forming wound dressing or skin coating material
WO1990006124A1 (en) * 1988-12-07 1990-06-14 Bentech Laboratories, Inc. Formulations for treating slow and non-healing wounds
US4920158A (en) * 1989-10-11 1990-04-24 Medipro Sciences Limited Hydrogel-forming wound dressing or skin coating material
US6150581A (en) * 1995-06-07 2000-11-21 United States Surgical Corporation Chitosan/alginate anti-adhesion barrier
US5733884A (en) * 1995-11-07 1998-03-31 Nestec Ltd. Enteral formulation designed for optimized wound healing
US6117851A (en) * 1996-12-13 2000-09-12 Lescarden Inc. Treatment of osteoarthritis by administering poly-N-acetyl-D-glucosamine
US20040247632A1 (en) * 1999-12-23 2004-12-09 Ivrea, Inc. Chitosan microparticles for the topical delivery of water insoluble active agents
US20050245482A1 (en) * 2000-03-15 2005-11-03 Weiyu Fan Chitosan and method of preparing chitosan
US7413881B2 (en) 2000-03-15 2008-08-19 Cargill, Incorporated Chitosan and method of preparing chitosan
US6444797B1 (en) 2000-07-18 2002-09-03 Ibeks Technologies Co., Ltd. Chitosan microflake and method of manufacturing the same
US20030206958A1 (en) * 2000-12-22 2003-11-06 Cattaneo Maurizio V. Chitosan biopolymer for the topical delivery of active agents
US8859528B2 (en) 2001-02-12 2014-10-14 Marine Polymer Technologies, Inc. Compositions and methods for modulation of vascular structure and/or function
US20100323986A1 (en) * 2001-02-12 2010-12-23 Marine Polymer Technologies, Inc., Compositions and methods for modulation of vascular structure and/or function
US8481512B2 (en) 2001-02-12 2013-07-09 Marine Polymer Technologies, Inc. Compositions and methods for modulation of vascular structure and/or function
US7816514B2 (en) 2001-02-16 2010-10-19 Cargill, Incorporated Glucosamine and method of making glucosamine from microbial biomass
US8222232B2 (en) 2001-02-16 2012-07-17 Cargill, Incorporated Glucosamine and N-acetylglucosamine compositions and methods of making the same fungal biomass
US20060178344A1 (en) * 2001-02-16 2006-08-10 Cargill, Incorporated Glucosamine and N-acetylglucosamine and methods of making the same fungal biomass
US20060172392A1 (en) * 2001-02-16 2006-08-03 Cargill, Incorporated Water soluble beta-glucan, glucosamine, and N-acetylglucosamine compositions and methods for making the same
US20030148998A1 (en) * 2001-02-16 2003-08-07 Cargill, Incorporated Glucosamine and method of making glucosamine from microbial biomass
US20040077055A1 (en) * 2001-02-16 2004-04-22 Cargill, Incorporated Glucosamine and method of making glucosamine from microbial biomass
US8034925B2 (en) 2001-02-16 2011-10-11 Cargill, Incorporated Glucosamine and method of making glucosamine from microbial biomass
US7923437B2 (en) 2001-02-16 2011-04-12 Cargill, Incorporated Water soluble β-glucan, glucosamine, and N-acetylglucosamine compositions and methods for making the same
US20060004314A1 (en) * 2001-06-14 2006-01-05 Hemcon, Inc. Antimicrobial barriers, systems, and methods formed from hydrophilic polymer structures such as chistosan
US7482503B2 (en) 2001-06-14 2009-01-27 Providence Health System-Oregon Wound dressing and method for controlling severe, life-threatening bleeding
US9132206B2 (en) 2001-06-14 2015-09-15 Hemcon Medical Technologies, Inc. Hemostatic compositions, assemblies, systems, and methods employing particulate hemostatic agents formed from hydrophilic polymer foam such as chitosan
US20110143312A1 (en) * 2001-06-14 2011-06-16 Hemcon Medical Technologies, Inc. Compositions, assemblies, and methods applied during or after a dental procedure to ameliorate fluid loss and/or promote healing, using a hydrophilic polymer sponge structure such as chitosan
US20050038369A1 (en) * 2001-06-14 2005-02-17 Gregory Kenton W. Wound dressing and method for controlling severe, life-threatening bleeding
US7820872B2 (en) 2001-06-14 2010-10-26 Providence Health System-Oregon Wound dressings, apparatus, and methods for controlling severe, life-threatening bleeding
US9004918B2 (en) 2001-06-14 2015-04-14 Hemcon Medical Technologies, Inc. Compositions, assemblies, and methods applied during or after a dental procedure to ameliorate fluid loss and/or promote healing, using a hydrophilic polymer sponge structure such as chitosan
US6693188B2 (en) 2001-08-08 2004-02-17 Cargill Incorporated N-acetyl-D-glucosamine and process for producing N-acetyl-D-glucosamine
US7488812B2 (en) 2002-04-02 2009-02-10 Cargill, Incorporated Chitosan production
US20090099347A1 (en) * 2002-04-02 2009-04-16 Cargill, Incorporated Chitosan production
US20050215774A1 (en) * 2002-04-02 2005-09-29 Trinkle Jamea R Chitosan production
US20110034410A1 (en) * 2002-06-14 2011-02-10 Mccarthy Simon J Wound dressing and method for controlling severe, life-threatening bleeding
US8269058B2 (en) 2002-06-14 2012-09-18 Hemcon Medical Technologies, Inc. Absorbable tissue dressing assemblies, systems, and methods formed from hydrophilic polymer sponge structures such as chitosan
US20090018479A1 (en) * 2002-06-14 2009-01-15 Hemcon Medical Technologies, Inc. Absorbable tissue dressing assemblies, systems, and methods formed from hydrophilic polymer sponge structures such as chistosan
US8668924B2 (en) 2002-06-14 2014-03-11 Providence Health System—Oregon Wound dressing and method for controlling severe, life-threatening bleeding
US8313474B2 (en) 2002-06-14 2012-11-20 Hemcon Medical Technologies, Inc. Method for preparing a compressed wound dressing
US20080213344A1 (en) * 2002-06-14 2008-09-04 Providence Health System- Oregon Wound dressing and method for controlling severe, life-threatening bleeding
US8741335B2 (en) 2002-06-14 2014-06-03 Hemcon Medical Technologies, Inc. Hemostatic compositions, assemblies, systems, and methods employing particulate hemostatic agents formed from hydrophilic polymer foam such as Chitosan
US7371403B2 (en) 2002-06-14 2008-05-13 Providence Health System-Oregon Wound dressing and method for controlling severe, life-threatening bleeding
US20080146984A1 (en) * 2002-06-14 2008-06-19 Hemcon Medical Technologies, Inc. Method for preparing a compressed wound dressing
US20040243043A1 (en) * 2002-06-14 2004-12-02 Mccarthy Simon J, Wound dressing and method for controlling severe, life-threatening bleeding
US20060246114A1 (en) * 2002-11-01 2006-11-02 Rogers Brent D Multiple component food product useful for delivering glucosamine and/or nacetyl-d-glucosamine
US20060058263A1 (en) * 2002-11-01 2006-03-16 Rogers Brent D Heat pasturized liquids containing glucosamine
US20060003965A1 (en) * 2002-11-01 2006-01-05 Fosdick Lawrence D N-acetyl-d-glucosamine (nag) supplemented food products and beverages
US8992453B2 (en) 2003-09-12 2015-03-31 Marine Polymer Technologies, Inc. Vascular access preservation in hemodialysis patients
US8951565B2 (en) 2003-12-23 2015-02-10 Hemcon Medical Technologies, Inc. Hemostatic compositions, assemblies, systems, and methods employing particulate hemostatic agents formed from hydrophilic polymer foam such as chitosan
US20050281886A1 (en) * 2004-05-06 2005-12-22 Ivrea Pharmaceuticals, Inc. Particles for the delivery of active agents
US20060141046A1 (en) * 2004-05-06 2006-06-29 Ivrea Pharmaceuticals, Inc. Particles for the delivery of active agents
US8263763B2 (en) 2004-06-18 2012-09-11 Taiwan Hopax Chemicals Manufacturing Company, Ltd. Chemically modified polyaminosaccharide by a hydrocarbyl sultone compound
US20050283004A1 (en) * 2004-06-18 2005-12-22 Hopax Chemicals Manufacturing Co., Ltd. Alkylsulfonated polyaminosaccharides
US20060025583A1 (en) * 2004-06-18 2006-02-02 Taiwan Hopax Chemicals Manufacturing Company, Ltd. Chemically modified polyaminosaccharide by a hydrocarbyl sultone compound
EP1607406A1 (en) 2004-06-18 2005-12-21 Taiwan Hopax Chems. Mfg. Co., Ltd Chemically modified polyaminosaccharide by a hydrocarbyl sultone compound
US9204957B2 (en) 2005-03-17 2015-12-08 Hemcon Medical Technologies, Inc. Systems and methods for hemorrhage control and or tissue repair
US20060211973A1 (en) * 2005-03-17 2006-09-21 Gregory Kenton W Systems and methods for hemorrhage control and or tissue repair
US20080287907A1 (en) * 2006-05-23 2008-11-20 Providence Health System-Oregan D/B/A Providence St. Vincent Medical Center Systems and methods for introducing and applying a bandage structure within a body lumen or hollow body organ
US8920514B2 (en) 2006-05-23 2014-12-30 Providence Health System—Oregon Systems and methods for introducing and applying a bandage structure within a body lumen or hollow body organ
US20090104284A1 (en) * 2007-10-19 2009-04-23 Gunn Jr Herbert Harrell Topically Applied Chitosan Composition for Pain Relief and Boosting Immune System
US9205170B2 (en) 2008-05-02 2015-12-08 Hemcon Medical Technologies, Inc. Wound dressing devices and methods
US20100172958A1 (en) * 2008-05-02 2010-07-08 Hemcon Medical Technologies, Inc. Wound dressing devices and methods
US8517979B2 (en) 2008-12-22 2013-08-27 Abbott Laboratories Carriers for hemostatic tract treatment
US20100228185A1 (en) * 2008-12-22 2010-09-09 Abbott Laboratories Carriers for hemostatic tract treatment
US9533076B2 (en) 2008-12-22 2017-01-03 Abbott Laboratories Carriers for hemostatic tract treatment
US8389498B2 (en) 2010-03-26 2013-03-05 Taiwan Textile Research Institute Spinning solution and method for manufacturing biomaterial fibers
US20110237539A1 (en) * 2010-03-26 2011-09-29 Taiwan Textile Research Institute Spinning Solution and Method for Manufacturing Biomaterial Fibers
US8715719B2 (en) 2010-06-16 2014-05-06 Abbott Vascular, Inc. Stable chitosan hemostatic implant and methods of manufacture

Similar Documents

Publication Publication Date Title
Muzzarelli et al. Chitin nanofibrils/chitosan glycolate composites as wound medicaments
US4929722A (en) Acid decrystallization of aminopolysaccharides and derivatives thereof
Aranaz et al. Functional characterization of chitin and chitosan
US5783569A (en) Uses for underivatized, aqueous soluble β(1-3) glucan and compositions comprising same
EP0263490A2 (en) Sustained-release particulate preparation and process for preparing the same
US3987166A (en) Treatment of tumors with glucan compositions in mice and rats
US5488040A (en) Use of neutral soluble glucan preparations to stimulate platelet production
Parr et al. Similarities of the anti-tumour actions of endotoxin, lipid A and double-stranded RNA
US5925626A (en) Hyaluronic acid fractions having pharmaceutical activity, and pharmaceutical compositions containing the same
Muzzarelli Biochemical significance of exogenous chitins and chitosans in animals and patients
US20030078209A1 (en) Solid compositions exhibiting iron binding activity
Şenel et al. Potential applications of chitosan in veterinary medicine
Muzzarelli et al. Reconstruction of parodontal tissue with chitosan
EP0138572A2 (en) Hyaluronic acid fractions having pharmaceutical activity, methods for preparation thereof, and pharmaceutical compositions containing the same
US5442053A (en) Salts and mixtures of hyaluronic acid with pharmaceutically active substances, pharmaceutical compositions containing the same and methods for administration of such compositions
US5849720A (en) Enhancement of non-specific immune defenses by administration of underivatized, aqueous soluble glucans
Blaine Experimental observations on absorbable alginate products in surgery: gel, film, gauze and foam
Hwang et al. Chitinous materials inhibit nitric oxide production by activated RAW 264.7 macrophages
Kumar A review of chitin and chitosan applications
Jayakumar et al. Novel carboxymethyl derivatives of chitin and chitosan materials and their biomedical applications
EP0436110A1 (en) Pankreatin preparations
EP0224987A2 (en) Drug delivery systems based on hyaluronan, derivatives thereof and their salts and method of producing same
US5811542A (en) Method for producing soluble glucans
US20070148215A1 (en) Therapeutically active dressings, their manufacture and use
US7115588B2 (en) Methods for treating a breach or puncture in a blood vessel

Legal Events

Date Code Title Description
AS Assignment

Owner name: LESCARDEN INC.,

Free format text: CHANGE OF NAME;ASSIGNOR:LESCARDEN LTD.;REEL/FRAME:004123/0510

Effective date: 19830105