The invention relates to conjugates of hyaluronic acid oligomer according to the general formulae I, II III or IV, or a salt thereof, the method of preparation thereof and use thereof, where the oligomer is bonded to the respective substrate by its ending anomeric center via a bi-functional amino linker by means of an amino or imino bond. This type of conjugates allows releasing oligomers in their native form. The prepared systems exhibited an enhanced biological activity against selected lines of cancer cells.
A61K 47/48 - Préparations médicinales caractérisées par les ingrédients non actifs utilisés, p.ex. supports, additifs inertes l'ingrédient non actif étant chimiquement lié à l'ingrédient actif, p.ex. conjugués polymère-médicament
C08B 37/00 - Préparation des polysaccharides non prévus dans les groupes Leurs dérivés
2.
VOLUMINOUS NANOFIBROUS MATERIAL BASED ON HYALURONIC ACID, ITS SALT OR THEIR DERIVATIVES, METHOD OF PREPARATION THEREOF, METHOD OF MODIFICATION THEREOF, MODIFIED NANOFIBROUS MATERIAL, NANOFIBROUS STRUCTURE AND USE THEREOF
The invention relates to voluminous nanofibrous materials based on hyaluronic acid, salts thereof or their derivatives, wherein the volumetric weight is within the range of 1 kg.m-3 to 100 kg.m-3. The preparation of such materials is conditioned especially by the relative humidity in the spinning chamber and the viscosity of the spinning solution. The voluminous nanofibrous materials prepared from photoactive derivatives of hyaluronic acid may be crosslinked by means of UV radiation or by heat treatment. The voluminous nanofibrous materials may be shaped to any nanofibrous structure by means of a weld. The disclosed materials and structures may be used in medicine or cosmetics.
D01F 9/00 - Filaments, ou similaires, faits par l’homme, formés d’autres substancesLeur fabricationAppareils spécialement adaptés à la fabrication de filaments de carbone
D01D 5/00 - Formation des filaments, fils ou similaires
C08B 37/08 - ChitineSulfate de chondroïtineAcide hyaluroniqueLeurs dérivés
3.
NANOFIBERS CONTAINING PHOTOCURABLE ESTER DERIVATIVE OF HYALURONIC ACID OR ITS SALT, PHOTOCURED NANOFIBERS, METHOD OF SYNTHESIS THEREOF, PREPARATION CONTAINING PHOTOCURED NANOFIBERS AND USE THEREOF
The invention relates to nanofibers containing photocurable ester derivatives of hyaluronic acid or its salt, the method of preparation thereof, and the photocured preparation made from the nanofibers by light irradiation and the use thereof
The invention relates to a cosmetic composition based on hyaluronic acid, which includes nanofibres comprising hyaluronic acid or a pharmaceutically acceptable salt thereof and at least one carrier polymer, preferably polyethylene oxid, polyvinyl alcohol. Further, it discloses the method of production of said composition which is carried out by means of electrostatic spinning of the mixture in water.
A61Q 19/00 - Préparations pour les soins de la peau
A61K 8/81 - Cosmétiques ou préparations similaires pour la toilette caractérisés par la composition contenant des composés organiques macromoléculaires obtenus par des réactions faisant intervenir uniquement des liaisons insaturées carbone-carbone
A61Q 19/08 - Préparations contre le vieillissement
A61K 8/97 - Cosmétiques ou préparations similaires pour la toilette caractérisés par la composition contenant des produits de constitution indéterminée ou leurs dérivés à base d’algues, de champignons, de lichens ou de plantesCosmétiques ou préparations similaires pour la toilette caractérisés par la composition contenant des produits de constitution indéterminée ou leurs dérivés à base de leurs dérivés
A61K 8/02 - Cosmétiques ou préparations similaires pour la toilette caractérisés par une forme physique particulière
5.
METHOD OF PREPARATION OF 2-OXOGLUTARATE ESTER, PREPARATION CONTAINING 2-OXOGLUTARATE ESTER AND USE THEREOF
The invention relates to a method of preparation of 2-oxoglutarate ester, a preparation containing 2-oxoglutarate ester and use thereof for supporting collagen biosynthesis.
C07C 67/08 - Préparation d'esters d'acides carboxyliques par réaction d'acides carboxyliques ou d'anhydrides symétriques avec le groupe hydroxyle ou O-métal de composés organiques
C07D 333/16 - Radicaux substitués par des hétéro-atomes, autres que les halogènes, liés par des liaisons simples par des atomes d'oxygène
C07D 295/088 - Composés hétérocycliques contenant des cycles polyméthylène imine d'au moins cinq chaînons, des cycles aza-3 bicyclo [3.2.2] nonane, piperazine, morpholine ou thiomorpholine, ne comportant que des atomes d'hydrogène liés directement aux atomes de carbone du cycle avec des radicaux hydrocarbonés substitués liés aux atomes d'azote du cycle substitués par des atomes d'oxygène ou de soufre liés par des liaisons simples avec les atomes d'azote du cycle et les atomes d'oxygène ou de soufre liés à la même chaîne carbonée, qui n'est pas interrompue par des carbocycles à une chaîne acyclique saturée
A61K 8/49 - Cosmétiques ou préparations similaires pour la toilette caractérisés par la composition contenant des composés organiques contenant des composés hétérocycliques
A61Q 19/00 - Préparations pour les soins de la peau
6.
ENDLESS FIBRES ON THE BASIS OF HYALURONAN SELECTIVELY OXIDIZED IN THE POSITION 6 OF THE N-ACETYL-D-GLUCOSAMINE GROUP, PREPARATION AND USE THEREOF, THREADS, STAPLES, YARNS, FABRICS MADE THEREOF AND METHOD FOR MODIFYING THE SAME
The present invention relates to the preparation of textile processable endless monofilaments and multifilaments on the basis of hyaluronan which has been selectively oxidized to aldehyde in the position 6 of its /V-acetyl-D-glucosamine group and to the subsequent modification of such filaments with low molecular dihydrazides. The fibres as well as the fabrics, which are subsequently prepared from the former, exhibit a time-varying solubility in saline depending on the external modification of the fibres. After having been externally modified, the fibres as well as the fabrics exhibit a prolong period of transition into an evenly distributed gel layer. The externally modified fibrous materials retain their full biocompatibility.
D06M 23/10 - Procédés dans lesquels l'agent traitant est dissout ou dispersé dans des solvants organiquesProcédés pour la récupération de ces solvants organiques
D01F 9/00 - Filaments, ou similaires, faits par l’homme, formés d’autres substancesLeur fabricationAppareils spécialement adaptés à la fabrication de filaments de carbone
D02J 13/00 - Chauffage ou refroidissement de filaments, filés, fils câblés, cordes ou similaires ne correspondant spécifiquement à aucun des procédés prévus dans la présente sous-classe
7.
PHOTOREACTIVE DERIVATIVE OF HYALURONIC ACID, METHOD OF PREPARATION THEREOF, 3D-CROSSLINKED DERIVATIVE OF HYALURONIC ACID, METHOD OF PREPARATION AND USE THEREOF
The subject-matter of the invention is a photoreactive derivative of hyaluronic acid (formula I) and the method of preparation thereof, where first an aldehyde derivative of hyaluronic acid is prepared, oxidized in the position 6 of the glucosamine cycle and then the oxidized derivative reacts with an amine carrying a photoreactive species, for example l-(2- aminoethyl)pyridine-2(lH)-one, in the presence of a reducing agent, forming a photoreactive derivative. The prepared photoreactive derivative may be then photocrosslinked, wherein the reaction is based on [4+4] photocycloaddition. Moreover, the invention relates to a 3D- crosslinked derivative of hyaluronic acid (formula II) which exhibits an increased hydrolytic stability and improved sorption properties, with the possibility of a further design of the physical properties thereof according to the requirements of the final applications, and moreover, to the use thereof in tissue engineering, regenerative medicine, medical agents or formulations or cosmetics.
C6-C18-ACYLATED DERIVATIVE OF HYALURONIC ACID, METHOD OF PREPARATION THEREOF, NANOMICELLAR COMPOSITION ON ITS BASIS, METHOD OF PREPARATION THEREOF AND METHOD OF PREPARATION STABILIZED NANOMICELLAR COMPOSITION, AND USE THEREOF
The invention relates to a method of preparation hydrophobized hyaluronic acid (Formula I) and further to a method of encapsulating biologically active substances into the nanomicelles of hydrophobized hyaluronan serving as carriers of biologically active hydrophobic substances. The hydrophobization of hyaluronan is carried out through an esterification reaction of hyaluronan with long-chain carboxylic acids, the latter being activated by a halogenide derivative of 2,4,6-trichlorobenzoic acid or by another organic chloride. In an aqueous environment, water-soluble hydrophobized derivatives can form nanomicelles in which nonpolar substances can be bound by means of non-covalent physical interactions. The core of a nanomicelle is formed by hydrophobic acyl functional groups while the shell of a nanomicelle is formed by hyaluronic acid. The encapsulation of the substances into nanomicelles can be performed by means of the solvent exchange method or by means of sonication. Hyaluronic nanomicelles support the penetration of bound substances in topical applications and enable the bound substances to be transferred into the individual cells. The nanomicelles obtained from hydrophobized hyaluronan derivatives are usable in cosmetic and pharmaceutical applications.
The invention relates to the biodegradable fibres which are based on hydrophobic derivatives of hylauronan, specifically on the base of the hyaluronan derivative C11-C18-acylated on hydroxyl groups of hyaluronic acid, and use thereof. Further the invention relates to the preparation of these fibres which is performed with the use of the wet spinning method in a coagulation bath comprising water solution of organic acid, with the production of continuous monofiles which can be thereafter processed to threads and further to textiles, knitted textiles, or nonwoven textiles. These textiles, knitted textiles or nonwoven textiles can be used for example for the production of implantable surgicalmaterial for human and veterinary medicine.
C08B 37/08 - ChitineSulfate de chondroïtineAcide hyaluroniqueLeurs dérivés
D01F 9/00 - Filaments, ou similaires, faits par l’homme, formés d’autres substancesLeur fabricationAppareils spécialement adaptés à la fabrication de filaments de carbone
The invention relates to an enzyme which is able to degrade hyaluronic acid and which is produced by fungi of the genus Fistulina (especially Fistulina hepatica). The degradation proceeds by lyase mechanism in which double bonds between C4 and C5 of glucuronic acid are formed. The invention also includes the process of preparation and purification of the enzyme and a possible practical use thereof for the preparation of low-molecular hyaluronan or of cosmetic or pharmaceutical devices. Further, the invention relates to the method of preparation of low-molecular hyaluronan.
C07K 14/375 - Peptides ayant plus de 20 amino-acidesGastrinesSomatostatinesMélanotropinesLeurs dérivés provenant de champignons provenant de Basidiomycetes
C12P 19/04 - Polysaccharides, c.-à-d. composés contenant plus de cinq radicaux saccharide reliés entre eux par des liaisons glucosidiques
11.
HYALURONIC ACID DERIVATIVE, METHOD OF PREPARATION THEREOF, METHOD OF MODIFICATION THEREOF AND USE THEREOF
The invention relates to the preparation and use of α,β-unsaturated aldehyde of hyaluronan having a double bond in the positions 4 and 5 and an aldehydic group in the position 6 of the glucosamine part of the polysaccharide. The method of preparation is based on dehydration of hyaluronan having an aldehydic group in the position 6 of the glucosamine part of the polysaccharide. Two methods have been described, which are dehydration in a solution or heating in solid state in absence of solvents, bases or other additives. This derivative allows stabilization of conjugates of hyaluronan with amino compounds by means of a multiple bond from the aldehyde side, and therefore, it is possible to effectively immobilize practically any compound containing an amino group to such modified hyaluronan in physiological conditions. In case of using a diamine or compounds or polymers containing three or more amino groups, it is possible to prepare crosslinked hyaluronan derivatives. The described solution brings along a significant advantage not only in the field of carriers of biologically active substances, but also in tissue engineering where crosslinking with biologically acceptable amino compounds in physiological conditions is very much demanded.
Spinning nozzle for production of nanofibrous and microfibrous materials comprises: a first plate (1) provided with at least one continuous groove (2) for directing a first material to an outlet mouth portion (3) of the continuous groove (2) in a face (4) of the first plate (1); a second plate (5) provided with at least one continuous groove (6) for directing a second material to an outlet mouth portion (7) of the continuous groove (6) of the second plate (5), the outlet mouth portion (7) being arranged adjacent to the outlet mouth portion (3) of the first plate (1); and a separating plate (8) arranged between the first plate (1) and the second plate (5) for separating the continuous grooves (2) of the first plate (1) from the continuous grooves (6) of the second plate (5), while the face (9) of the separating plate (8) forms with the face (4) of the first plate (1) and/or the face (10) of the second plate (5) a continuous surface in the region of the outlet mouth portions (3; 7) of the continuous grooves (2; 6).
METHOD OF PREPARATION OF POLYSACCHARIDE FIBERS, WOUND COVERS THAT CONTAIN THEM, METHOD OF MANUFACTURING OF WOUND COVERS, AND APPARATUS FOR PREPARATION OF POLYSACCHARIDE FIBERS
The invention relates to the method of the preparation of polysaccharide fibres based on hyaluronic acid, a compound comprising hyaluronic acid and metal ions, schizophylan, chitin/chitosan-glucan complex, a compound comprising chitin/chitosan-glucan complex and metal ions, internal mixture of chitin and chitosan, a compound comprising internal mixture of chitin and metal ions, sodium alginate, potassium alginate, ammonium alginate, xanthane, xanthane sodium salt, xanthane potassium salt, oxycellulose, oxycellulose sodium salt, oxycellulose potassium salt, carboxymethyl cellulose, carboxymethyl cellulose sodium salt, and carboxymethyl cellulose potassium salt, or a mixture of polysaccharides, in a non-stationary coagulation bath comprisin a C1 -C3 alcohol. Further the invention relates to covers of internal and external wounds and skin defects based on these fibres, and a method of production thereof, and the apparatus for the preparation of polysaccharide fibres.
D01D 5/40 - Formation des filaments, fils ou similaires par application à la dispersion ou à la solution de polymères destinée à former les filaments d'une force de cisaillement, p. ex. par agitation
D01F 2/24 - Filaments, ou similaires, artificiels, à un seul composant, formés de cellulose ou de dérivés de la celluloseLeur fabrication à partir de dérivés de la cellulose
D01F 9/00 - Filaments, ou similaires, faits par l’homme, formés d’autres substancesLeur fabricationAppareils spécialement adaptés à la fabrication de filaments de carbone
D01F 9/04 - Filaments, ou similaires, faits par l’homme, formés d’autres substancesLeur fabricationAppareils spécialement adaptés à la fabrication de filaments de carbone d'alginates
D06M 11/83 - Traitement des fibres, fils, filés, tissus ou des articles fibreux faits de ces matières, avec des substances inorganiques ou leurs complexesUn tel traitement combiné avec un traitement mécanique, p. ex. mercerisage avec des métauxTraitement des fibres, fils, filés, tissus ou des articles fibreux faits de ces matières, avec des substances inorganiques ou leurs complexesUn tel traitement combiné avec un traitement mécanique, p. ex. mercerisage avec des composés libérant des métaux, p. ex. des métaux-carbonylesRéduction de composés métalliques sur des textiles
D04H 1/42 - Non-tissés formés uniquement ou principalement de fibres coupées ou autres fibres similaires relativement courtes à partir de voiles ou couches composés de fibres ne possédant pas des propriétés cohésives réelles ou potentielles caractérisés par l'emploi de certaines sortes de fibres dans la mesure où cet emploi n'a pas d'influence prépondérante sur la consolidation du voile
The invention relates to a crosslinked hyaluronan derivative in the form of a hydrogel or microfibers, and to a method of preparation thereof, consisting in a C-C coupling reaction. The C-C coupling reaction is performed via reaction of a hyaluronan derivative carrying a terminal aryl-halide and/or aryl-borate group, and a hyaluronan derivative carrying an alkenyl or alkynyl group, in water, phosphates buffer or a mixture of an organic acid and an alcohol, and in the presence of a palladium active catalyst. The palladium active catalyst may be e.g. a complex of palladium (II) acetate and an inorganic or organic base, or a complex of palladium (II) and 2-amino-4,6-dihydroxypyrimidine.
C08B 37/08 - ChitineSulfate de chondroïtineAcide hyaluroniqueLeurs dérivés
15.
DERIVATES BASED ON HYALURONIC ACID, CAPABLE OF FORMING HYDROGELS, METHOD OF PREPARATION THEREOF, HYDROGELS BASED ON SAID DERIVATIVES, METHOD OF PREPARATION THEREOF AND USE
The invention relates to a new hyaluronan derivative according to the general formula (I), the method of preparation thereof, a hydrogel based on the new derivative, method of preparation of the hydrogel and the use of the hydrogel in tissue engineering, cosmetics, medicine or regenerative medicine, especially in the form of scaffolds for the tratment of articular cartilage or bone tissue defects.
A61K 47/36 - PolysaccharidesLeurs dérivés, p. ex. gommes, amidon, alginate, dextrine, acide hyaluronique, chitosane, inuline, agar-agar ou pectine
A61K 47/48 - Préparations médicinales caractérisées par les ingrédients non actifs utilisés, p.ex. supports, additifs inertes l'ingrédient non actif étant chimiquement lié à l'ingrédient actif, p.ex. conjugués polymère-médicament
16.
A METHOD FOR PRODUCTION OF MATERIALS HAVING ANISOTROPIC PROPERTIES COMPOSED OF NANOFIBRES OR MICROFIBRES AND AN APPARATUS FOR IMPLEMENTATION OF SAID METHOD
The present invention relates to a method of production of two-dimensional or three- dimensional fibrous materials of fibres (5) with a diameter ranging from microfibres to nanofibres, in which at first the fibre (5) is continuously drawn out of a solution (1) and is pulled to a rotary set (11) of n electrodes (6) by means of electrostatic field. The individual electrodes (6) of the set (11) are arranged at regular spacing to each other and at the same distance from the set (11) of electrodes (6) rotation axis and parallel with it. The fibre (5) is wound on the rotating set (11) of the electrodes (6). After a layer (8) of the fibres, (5) was formed, the electrostatic field is disconnected and rotation of the set (11) of the electrodes (6) is stopped, and the layer (8) of the fibres (5) formed in a field between two adjacent electrodes (6) is removed. In a subsequent step the rotating set (11) of the electrodes (6) turn through an angle of 360/n°, and the layer (8) of the fibres (5) formed between two adjacent electrodes (6) in the field adjacent to the field, from which the layer (8) was removed in preceding step, is removed. This step is repeated in total n-times. The solution also relates to an apparatus for implementation of the method, the apparatus comprising at least one spinning nozzle (3) connected to a first potential, the pivoted set (11) of the electrodes (6), facing the nozzle and the accumulator (7) for collecting fibres (5) settled between two adjacent electrodes (6). The accumulator (7) is, in relation to the electrodes (6), arranged movably in the direction of longitudinal axes of the electrodes (6) for collecting the fibres (5) settled between two adjacent electrodes (6), and is, in relation to the electrodes (6), arranged movably in the direction perpendicular to the longitudinal axes of the electrodes (6) for it being brought into engagement to collect fibres; (5) settled between two adjacent electrodes (6), and being brought out of engagement after finishing the collection of fibres (5) settled between two adjacent electrodes (6).
D01D 7/00 - Réception des produits nouvellement filés
D01D 5/00 - Formation des filaments, fils ou similaires
17.
AMPHOTERIC MATERIALS BASED ON CROSSLINKED HYALURONIC ACID, METHOD OF PREPARATION THEREOF, MATERIALS CONTAINING ENTRAPPED ACTIVE AGENTS, METHOD OF PREPARATION THEREOF, AND USE OF SAID MATERIALS
The present invention describes novel amphoteric materials based on crosslinked hyaluronic acid, according to the general formula (I), and a method of preparation of said materials. Further, the invention relates to the material containing entrapped active agents (e.g. drugs, growth factors etc.) and a method of preparation thereof. Moreover, the present invention relates to the use of said materials for controlled release systems, in tissue engineering, wound dressing or tissue regeneration.
The invention relates to the method of preparation of hyaluronic acid-based fibres, where first the spinning solution of hyaluronic acid and/or a metal compound thereof, optionally containing a metal salt or a hyaluronic acid compound and metal ions, is prepared, then the spinning solution is introduced into the coagulation bath comprising an acid, an alcohol and not more than 10 %wt. of water, and optionally a metal salt, resulting in forming a fibre which is preferably left in the coagulation bath and/or is drawn, then the fibre is washed with alcohol and dried. After washing of the fibre, metal ions may be introduced in the fibre by means of the metalization bath. Further, the invention relates to the fibres based on hyaluronic acid and/or a metal compound thereof, having the fibre (monofilament) diameter 4 μm to 1 mm, linear weight 0.1 to 30 g/1000 m (0.1 to 30 tex), tensile strength 0.5 to 3 cN.dtex-1 and loop strength 20 to 80 % of the tensile strength. The invention also relates to a silk tow that contains 2 to 50 primary fibres. Moreover, the invention relates to the use of the fibres for the production of woven and non- swoven fabrics.
D01F 9/00 - Filaments, ou similaires, faits par l’homme, formés d’autres substancesLeur fabricationAppareils spécialement adaptés à la fabrication de filaments de carbone
D03D 15/00 - Tissus caractérisés par la matière, la structure ou les propriétés des fibres, des filaments, des filés, des fils ou des autres éléments utilisés en chaîne ou en trame
D04H 3/00 - Non-tissés formés uniquement ou principalement de fils ou de matériaux filamenteux similaires de bonne longueur
19.
METHOD OF PREPARATION OF HIGHLY SUBSTITUTED HYALURONIC ACID AMIDES
The invention relates to the method of preparation of highly substituted hyaluronic acid amides with a controllable degree of substitution, which are prepared in a polar aprotic environment from an acidic form of hyaluronic acid in the presence of ethylchloroformiate, by means of a primary amine.
An apparatus for a production of two-dimensional or three-dimensional fibrous materials of microfibers or nanofibers containing a set of spinning metal nozzles (3) connected to a first potential, a set of electrodes (6) of a collector facing the set of the nozzles (3), arranged at regular spacing and connected to a second potential, and a collecting plate (7) or a collecting cylinder (14) for collecting microfibers or nanofibers settled between couples of adjacent electrodes (6) of the collector. The substance of the invention is as follows: the set of the electrodes (6) of the collector contains at least two electrodes (6) of the collector arranged in a plane and the collecting plate (7) in line of its intersection or a tangent to the collecting cylinder (14), that is perpendicular to a contact line with the plane of the electrodes (6) of the collector, form with the plane of the electrodes (6) of the collector an angle α, the size of which ranging between 0° and 90°, the collecting plate (7) or the collecting cylinder (14) being supported movably in relation to the electrodes (6) of the collector in a direction lying in the plane that is perpendicular to the plane of the electrodes (6) of the collector and in which the axis of the electrode (6) lies, the direction of the collecting plate (7) or the collecting cylinder (14) movement forming with this electrode (6) axis an angle β, the size of which ranging between 0° and 90°. Such arrangement enables creating of large areal and voluminous objects of ordered nanofibers.
brevets