AR117364A1 - HYALURONIC ACID MODIFIED WITH ALDEHYDE AND METHOD FOR ITS PREPARATION - Google Patents
HYALURONIC ACID MODIFIED WITH ALDEHYDE AND METHOD FOR ITS PREPARATIONInfo
- Publication number
- AR117364A1 AR117364A1 ARP190103732A ARP190103732A AR117364A1 AR 117364 A1 AR117364 A1 AR 117364A1 AR P190103732 A ARP190103732 A AR P190103732A AR P190103732 A ARP190103732 A AR P190103732A AR 117364 A1 AR117364 A1 AR 117364A1
- Authority
- AR
- Argentina
- Prior art keywords
- hyaluronic acid
- modified hyaluronic
- cho
- modified
- metal ion
- Prior art date
Links
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
- C08B37/0063—Glycosaminoglycans or mucopolysaccharides, e.g. keratan sulfate; Derivatives thereof, e.g. fucoidan
- C08B37/0072—Hyaluronic acid, i.e. HA or hyaluronan; Derivatives thereof, e.g. crosslinked hyaluronic acid (hylan) or hyaluronates
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/73—Polysaccharides
- A61K8/735—Mucopolysaccharides, e.g. hyaluronic acid; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
- C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
- C08J3/075—Macromolecular gels
-
- 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
- C08L5/08—Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2305/00—Characterised by the use of polysaccharides or of their derivatives not provided for in groups C08J2301/00 or C08J2303/00
- C08J2305/08—Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2405/00—Characterised by the use of polysaccharides or of their derivatives not provided for in groups C08J2401/00 or C08J2403/00
- C08J2405/08—Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Dispersion Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Materials Engineering (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Gerontology & Geriatric Medicine (AREA)
- Dermatology (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
La presente se relaciona con un derivado de ácido hialurónico modificado, donde el grupo -CH₂-OH de por lo menos una unidad de N-acetil-D-glucosamina se ha modificado para formar un grupo aldehído que tiene la estructura -CH₂-O-CH₂-CHO, métodos para la preparación del mismo y sus aplicaciones. Reivindicación 4: Un método para la preparación del derivado de ácido hialurónico modificado de acuerdo con cualquiera de las reivindicaciones 1 a 3, que comprende los siguientes pasos: a) producir un ácido hialurónico modificado con glicerol, que se caracteriza por el hecho de que el grupo -CH₂-OH de por lo menos una unidad de N-acetil-D-glucosamina se ha modificado para obtener un resto de la siguiente fórmula grupos -CH₂-O-CH₂-CHOH-CH₂OH; b) disolver el ácido hialurónico modificado con glicerol en un medio acuoso para obtener un ácido hialurónico modificado con glicerol solubilizado; c) hacer reaccionar dicho ácido hialurónico modificado con glicerol solubilizado con un agente oxidante, preferentemente un peryodato, más preferentemente peryodato de sodio, para convertir por lo menos una parte de dichos grupos -CH₂-O-CH₂-CHOH-CH₂OH a grupos aldehído de la fórmula -CH₂-O-CH₂-CHO, para obtener así un derivado ácido hialurónico modificado con aldehído. Reivindicación 7: Un derivado de ácido hialurónico modificado obtenido mediante el método de acuerdo con cualquiera de las reivindicaciones 4 a 6, donde el derivado de ácido hialurónico modificado preferentemente i) tiene un grado de modificación de 1,0% a 20,0%, preferentemente de 1,0% a 15%, más preferentemente de 1,0% a 10%, más preferentemente de 1,5% a 10%, más preferentemente de 1,5% a 8%, más preferentemente de 1,8% a 7,0%, más preferentemente de 2,0% a 6,9%, donde el grado de modificación se define como el número de grupos -CH₂-O-CH₂-CHOH-CH₂OH dividido por el número total de unidades de N-acetil-D-glucosamina presentes en el ácido hialurónico modificado, y/o ii) tiene un peso molecular medio en peso de 0,1 a 2,5 MDa, preferentemente de 0,2 a 1,5 MDa, más preferentemente de 0,4 a 1,3 MDa, aún más preferentemente de 0,6 a 1,1 MDa, y/o iii) comprende por lo menos un unidad de disacárido de la estructura de fórmula (1), donde R es seleccionado entre H, un ión de metal alcalino, preferentemente Na, y un ión de metal alcalinotérreo, y opcionalmente comprende además por lo menos una unidad de disacárido de la estructura de fórmula (2), donde R¹, R², R³ y R⁴ son independientemente seleccionados entre H y -CH₂-CHO y R⁵ es seleccionado entre hidrógeno, un ión de metal alcalino, preferentemente Na, una sal de metal alcalinotérreo, y -CH₂-CHO, con la condición de que por lo menos uno de R¹, R², R³, R⁴ y R⁵ sea -CH₂-CHO y, si R¹ es -CH₂-CHO, por lo menos uno de R², R³, R⁴ y R⁵ sea -CH₂-CHO. Reivindicación 13: Un hidrogel entrecruzado, que comprende la unidad estructural de fórmula (3), donde “Ac” denota -C(O)CH₃ y R es seleccionado entre hidrógeno, un ión de metal alcalino, preferentemente Na, y un ión de metal alcalinotérreo.This relates to a modified hyaluronic acid derivative, where the -CH₂-OH group of at least one N-acetyl-D-glucosamine unit has been modified to form an aldehyde group having the structure -CH₂-O- CH₂-CHO, methods for its preparation and its applications. Claim 4: A method for the preparation of the modified hyaluronic acid derivative according to any of claims 1 to 3, comprising the following steps: a) producing a glycerol modified hyaluronic acid, characterized in that the -CH₂-OH group of at least one N-acetyl-D-glucosamine unit has been modified to obtain a residue of the following formula -CH₂-O-CH₂-CHOH-CH₂OH groups; b) dissolving the glycerol-modified hyaluronic acid in an aqueous medium to obtain a solubilized glycerol-modified hyaluronic acid; c) reacting said solubilized glycerol modified hyaluronic acid with an oxidizing agent, preferably a periodate, more preferably sodium periodate, to convert at least a part of said -CH₂-O-CH₂-CHOH-CH₂OH groups to aldehyde groups of the formula -CH₂-O-CH₂-CHO, to thus obtain an aldehyde modified hyaluronic acid derivative. Claim 7: A modified hyaluronic acid derivative obtained by the method according to any one of claims 4 to 6, wherein the modified hyaluronic acid derivative preferably i) has a degree of modification of 1.0% to 20.0%, preferably 1.0% to 15%, more preferably 1.0% to 10%, more preferably 1.5% to 10%, more preferably 1.5% to 8%, more preferably 1.8% at 7.0%, more preferably 2.0% to 6.9%, where the degree of modification is defined as the number of -CH₂-O-CH₂-CHOH-CH₂OH groups divided by the total number of N units -acetyl-D-glucosamine present in modified hyaluronic acid, and / or ii) has a weight average molecular weight of 0.1 to 2.5 MDa, preferably 0.2 to 1.5 MDa, more preferably 0 , 4 to 1.3 MDa, even more preferably 0.6 to 1.1 MDa, and / or iii) comprises at least one disaccharide unit of the structure of formula (1), where R is selected from H, an alkali metal ion, pr efferently Na, and an alkaline earth metal ion, and optionally further comprises at least one disaccharide unit of the structure of formula (2), where R¹, R², R³ and R⁴ are independently selected from H and -CH₂-CHO and R⁵ is selected from hydrogen, an alkali metal ion, preferably Na, an alkaline earth metal salt, and -CH₂-CHO, provided that at least one of R¹, R², R³, R⁴ and R⁵ is -CH₂-CHO and, if R¹ is -CH₂-CHO, at least one of R², R³, R⁴ and R⁵ is -CH₂-CHO. Claim 13: A cross-linked hydrogel, comprising the structural unit of formula (3), where "Ac" denotes -C (O) CH₃ and R is selected from hydrogen, an alkali metal ion, preferably Na, and a metal ion alkaline earth.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP18214028 | 2018-12-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR117364A1 true AR117364A1 (en) | 2021-07-28 |
Family
ID=65009544
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP190103732A AR117364A1 (en) | 2018-12-19 | 2019-12-18 | HYALURONIC ACID MODIFIED WITH ALDEHYDE AND METHOD FOR ITS PREPARATION |
Country Status (1)
| Country | Link |
|---|---|
| AR (1) | AR117364A1 (en) |
-
2019
- 2019-12-18 AR ARP190103732A patent/AR117364A1/en unknown
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