Hydrogen-bonding compounds, compositions comprising the same, and methods of preparing and using the same

Patent metadata

Field	Value
Publication number	US-11286231-B2
Application number	US-201716344452-A
Country	US
Kind code	B2
Filing date	Oct 26, 2017
Priority date	Oct 26, 2016
Publication date	Mar 29, 2022
Grant date	Mar 29, 2022

Abstract

Described herein are compounds having a hydrogen-bonding group and optionally a functional group for binding (e.g., covalently binding) the compound to another compound (e.g., hyaluronic acid and/or gelatin). A compound of the present invention may have a structure represented by and/or comprising Formula I, Formula II, Formula III, Formula IV, Formula IV′, Formula V, Formula V′, Formula VI, Formula VII, and/or Formula VIII as described herein. Compositions including compounds of the present invention along with methods of preparing and using the same are also described herein.

First claim

That which is claimed is:

1. A modified polysaccharide comprising at least one polysaccharide unit including a moiety having a structure represented by Formula IV or Formula V:

wherein
A and B are each independently selected from the group consisting of hydrogen, —OH, chlorine, fluorine, —CO 2 H, —CO 2 CH 3 , —NH 2 , and —NHCOCH 3 ;
Z is —NR 3 (CH 2 ) p —, —O(CH 2 ) p —, —NR 3 (CH 2 ) p O—, —NR 3 (CH 2 ) p NR 3 —;
R 2 is hydrogen or ═O;
R 3 is hydrogen or is absent;
R 4 is hydrogen or C 1 -C 4 alkyl; and
p is an integer from 0 to 11.

2. The modified polysaccharide of claim 1 , wherein the modified polysaccharide is hyaluronic acid.

3. The modified polysaccharide of claim 1 , wherein the moiety is bound to the at least one polysaccharide unit via a thiol linkage to provide a structure represented by Formula IV′ or Formula V′:

wherein
A and B are each independently selected from the group consisting of hydrogen, —OH, chlorine, fluorine, —CO 2 H, —CO 2 CH 3 , —NH 2 , and —NHCOCH 3 ;
Z is —NR 3 (CH 2 ) p —, —O(CH 2 ) p —, —NR 3 (CH 2 ) p O—, —NR 3 (CH 2 ) p NR 3 —;
R 2 is hydrogen or ═O;
R 3 is hydrogen or is absent;
R 4 is hydrogen or C 1 -C 4 alkyl; and
p is an integer from 0 to 11.

4. The modified polysaccharide of claim 1 , wherein the moiety has a structure selected from the group consisting of:

wherein A and B are each independently selected from the group consisting of hydrogen, —OH, chlorine, fluorine, —CO 2 H, —CO 2 CH 3 , —NH 2 , and —NHCOCH 3 .

5. The modified polysaccharide of claim 1 , wherein the moiety has a structure selected from the group consisting of:

wherein A and B are each independently selected from the group consisting of hydrogen, —OH, chlorine, fluorine, —CO 2 H, —CO 2 CH 3 , —NH 2 , and —NHCOCH 3 ; and
R 4 is hydrogen or C 1 -C 4 alkyl.

6. The modified polysaccharide of claim 5 , wherein R 4 is methyl.

7. The modified polysaccharide of claim 5 , wherein R 4 is hydrogen.

8. A modified gelatin comprising at least one moiety bound to the gelatin backbone via a thiol linkage to provide a structure represented by Formula IV′ or Formula V′:

wherein
A and B are each independently selected from the group consisting of hydrogen, —OH, chlorine, fluorine, —CO 2 H, —CO 2 CH 3 , —NH 2 , and —NHCOCH 3 ;
Z is —NR 3 (CH 2 ) p —, —O(CH 2 ) p —, —NR 3 (CH 2 ) p O—, —NR 3 (CH 2 ) p NR 3 —;
R 2 is hydrogen or ═O;
R 3 is hydrogen or is absent;
R 4 is hydrogen or C 1 -C 4 alkyl; and
p is an integer from 0 to 11.

Assignees

• Univ Wake Forest Health Sciences
• Univ Wake Forest

Inventors

• Welker Mark E
• Skardal Aleksander
• Weissenfluh Amber N
• Banks Surya

Classifications

• C07C251/24

  having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings · CPC title

• A61L27/222

  Gelatin · CPC title

• C07C235/46 Primary

  having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms · CPC title

• C07C235/48

  having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms · CPC title

• C07C215/50 Primary

  with amino groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain · CPC title