# US 12,595,318 B2 · Crosslinked alginic acid > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 12,595,318 B2 - Document ID: US12595318B2 - Status: Granted - Kind: B2 - Application number: 18/428,348 - Filed: 2024-01-31 - Published: 2024-05-30 - Granted: 2026-04-07 - Earliest claimed: 2018-06-14 - Assignees: Mochida Pharmaceutical Co., Ltd. - Applicants: Mochida Pharmaceutical Co., Ltd. - Inventors: Shoji Furusako; Tomohiro Narumi; Tsutomu Satoh - Web page: https://patentgrep.com/patent/US12595318B2 ## CPC - C08B 37/0084: {Guluromannuronans, e.g. alginic acid, i.e. D-mannuronic acid and D-guluronic acid units linked with alternating alpha- and beta-1,4-glycosidic bonds; Derivatives thereof, e.g. alginates} - A61L 15/28: Polysaccharides or their derivatives {(A61L15/225 takes precedence)} - A61L 26/0023: {Polysaccharides} - A61L 27/20: Polysaccharides - C08J 3/24: Crosslinking, e.g. vulcanising, of macromolecules (mechanical aspects B29C35/00; crosslinking agents C08K) - C12N 5/0068: {General culture methods using substrates (for specific animal cell type C12N5/06)} - C08J 2305/04: Alginic acid; Derivatives thereof - C12N 2533/74: Alginate - C08B: POLYSACCHARIDES; DERIVATIVES THEREOF (polysaccharides containing less than six saccharide radicals attached to each other by glycosidic linkages C07H; fermentation or enzyme-using processes C12P19/00; sugar industry C13; production of cellulose D21) - 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 (preservation of bodies or disinfecting characterised by the agents employed A01N; preserving, e.g. sterilising, food or foodstuffs A23; preparations for medical, dental or toiletry purposes A61K) - C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29) - C12N: MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA (microbiological testing media C12Q1/00) ## Abstract The present invention provides alginic acid derivatives represented by formula (I) and formula (II), and a novel crosslinked alginic acid obtained by carrying out a Huisgen reaction using an alginic acid derivative of formula (I) and an alginic acid derivative of formula (II). There are thereby provided novel alginic acid derivatives and a novel crosslinked alginic acid. ## Claims ### Claim 1 An alginic acid derivative of formula (II) below, consisting of an azide group introduced via an amide bond and a divalent linker (-L2-) at any one or more carboxyl groups of alginic acid: in formula (II), (ALG) is alginic acid; —NHCO— is an amide bond via any carboxyl group of alginic acid; and -L2- is a divalent linker selected from the group consisting of the following partial structural formula, excluding the parts outside the cutting lines at both ends of each formula: ### Claim 2 (depends on 1) The alginic acid derivative of formula (II) according to claim 1, wherein the introduction rate of the N3-L2-NH2 group is 0.1% to 30%, wherein -L2- is defined as in claim 1. ### Claim 3 (depends on 1) The alginic acid derivative of formula (II) according to claim 1, wherein the weight-average molecular weight as measured by gel filtration chromatography of the alginic acid derivative is 100,000 Da to 3,000,000 Da. ### Claim 4 (depends on 1) The alginic acid derivative according to claim 1, wherein the alginic acid derivative has biocompatibility. ### Claim 5 An alginic acid derivative selected from the group consisting of the following formula: wherein in each formula, (ALG) is alginic acid; —NHCO— bound to (ALG) is an amide bond via any carboxyl group of alginic acid. ### Claim 6 (depends on 5) The alginic acid derivative according to claim 5, wherein the introduction rate of the azide-containing group is 0.1% to 30%. ### Claim 7 (depends on 5) The alginic acid derivative according to claim 5, wherein the weight-average molecular weight as measured by gel filtration chromatography of the alginic acid derivative is 100,000 Da to 3,000,000 Da. ### Claim 8 (depends on 5) The alginic acid derivative according to claim 5, wherein the alginic acid derivative has biocompatibility. ### Claim 9 (depends on 1) A method for producing the alginic acid derivative of formula (II) according to claim 1 or a salt thereof, the method comprising: causing a condensation reaction of an alginic acid or a salt thereof with an amine derivative of Formula (AM-2) or a salt thereof by using a condensing agent to obtain the alginic acid derivative of formula (II) or a salt thereof, wherein Formula (II): in formula (II), (ALG) is alginic acid; —NHCO— is an amide bond via any carboxyl group of alginic acid; and -L2- is a divalent linker selected from the group consisting of the following partial structural formula, excluding the parts outside the cutting lines at both ends of each formula: Formula (AM-2): in formula (AM-2), -L2- is defined as in formula (II). ### Claim 10 (depends on 9) The method for producing the alginic acid derivative of formula (II) or a salt thereof according to claim 9, wherein the condensing agent is 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methyl morpholinium chloride (DMT-MM). ### Claim 11 (depends on 9) The method for producing the alginic acid derivative represented by formula (II) or a salt thereof according to claim 9, wherein a solvent in the reaction is a mixed solvent of water and a solvent selected from the ether solvents, the alcohol solvents and the polar solvents. ### Claim 12 (depends on 9) The method for producing the alginic acid derivative of formula (II) or a salt thereof according to claim 9, wherein a solvent in the reaction is a mixed solvent of water and ethanol. ### Claim 13 (depends on 9) The method for producing the alginic acid derivative of formula (II) or a salt thereof according to claim 9, wherein the condensation reaction is performed with an inorganic base or an organic base. ### Claim 14 (depends on 9) The method for producing the alginic acid derivative of formula (II) or a salt thereof according to claim 9, wherein the condensation reaction is performed with an inorganic base. ### Claim 15 (depends on 9) The method for producing the alginic acid derivative of formula (II) or a salt thereof according to claim 9, wherein the condensation reaction is performed with sodium hydrogen carbonate. ### Claim 16 (depends on 9) The method for producing the alginic acid derivative of formula (II) or a salt thereof according to claim 9, wherein the salt of alginic acid is sodium alginate. ### Claim 17 (depends on 9) The method for producing the alginic acid derivative of formula (II) or a salt thereof according to claim 9, wherein the introduction rate of the N3-L2-NH2 group in the alginic acid derivative of formula (II) or a salt thereof is 0.1% to 30%, and -L2- is defined as in claim 9. ### Claim 18 (depends on 9) The method for producing the alginic acid derivative of formula (II) or a salt thereof according to claim 9, wherein the weight-average molecular weight as measured by gel filtration chromatography of the alginic acid derivative represented by formula (II) or a salt thereof is 100,000 Da to 3,000,000 Da.