IP Library › Granted Patent US 12,649,799
Granted Patent B2
US 12,649,799 · App. 18/428,348 · Granted Jun 9, 2026

Crosslinked alginic acid

Inventors: Shoji Furusako (Tokyo, JP); Tomohiro Narumi (Tokyo, JP); Tsutomu Satoh (Tokyo, JP)
Assignee: MOCHIDA PHARMACEUTICAL CO., LTD.
C08B37/0084A61L15/28A61L26/0023A61L27/20C08J3/24C12N5/0068C08J2305/04C12N2533/74
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Quick Facts
Patent No.
US 12,649,799
App. No.
18/428,348
Granted
Jun 9, 2026
Kind
B2
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 (24)

1 . An alginic acid derivative of formula (II) below, consisting of an azide group introduced via an amide bond and a divalent linker (-L 2 -) 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 -L 2 - 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:

2 . The alginic acid derivative of formula (II) according to claim 1 , wherein the introduction rate of the N 3 -L 2 -NH 2 group is 0.1% to 30%, wherein -L 2 - is defined as in claim 1 .

3 . 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.

4 . The alginic acid derivative according to claim 1 , wherein the alginic acid derivative has biocompatibility.

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.

6 . The alginic acid derivative according to claim 5 , wherein the introduction rate of the azide-containing group is 0.1% to 30%.

7 . 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.

8 . The alginic acid derivative according to claim 5 , wherein the alginic acid derivative has biocompatibility.

9 . 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 -L 2 - 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), -L 2 - is defined as in formula (II).

10 . 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).

11 . 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.

12 . 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.

13 . 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.

14 . 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.

15 . 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.

16 . 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.

17 . 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 N 3 -L 2 -NH 2 group in the alginic acid derivative of formula (II) or a salt thereof is 0.1% to 30%, and -L 2 - is defined as in claim 9 .

18 . 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.

Priority Claims (2)
JP 2018-113767 · Jun 14, 2018 · national
JP 2018-205668 · Oct 31, 2018 · national
Continuity (3)
Continuation 17119681 · Dec 11, 2020
Continuation In Part PCTJP2019023478 · Jun 13, 2019
Related Publication 20240174772A1 · May 30, 2024
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