Pendant hydrophile bearing biodegradable compositions and related devices

Patent metadata

Field	Value
Publication number	US-9387281-B2
Application number	US-201113880666-A
Country	US
Kind code	B2
Filing date	Oct 20, 2011
Priority date	Oct 20, 2010
Publication date	Jul 12, 2016
Grant date	Jul 12, 2016

Abstract

A composition comprising at least one polymer having the structure A-B-A′, wherein A and A′ may be the same or different and each is a degradable polyester component and wherein B is the reaction product resulting from the reaction between a diol, having one or more pendant oligomeric or polymeric groups, and A and A′. Additionally, a bioresorbable patch comprising: (a) an adhesion barrier component comprising the composition in the form of a film; and (b) an adhesive component comprising (i) at least one synthetic adhesive polymer and/or (ii) at least one polysaccharide. Also, a method of wound healing, comprising administering the composition or apply the patch to a patient.

First claim

The invention claimed is:

1. A composition comprising at least one polymer having the structure A-B-A′, wherein A and A′ may be the same or different and each is a degradable aliphatic polyester component and wherein B is the reaction product resulting from the reaction between (i) A and A′ and (ii) a diol, having one or more pendant oligomeric or polymeric groups, wherein B includes a pendant oligomeric or polymeric oxyalkylene moiety.

2. The composition of claim 1 wherein A and A′ each comprise a poly(hydroxy carboxylic acid).

3. The composition of claim 2 , wherein said poly (hydroxy carboxylic acid) is a member selected from the group consisting of glycolide, lactide, β-propiolactone, β-butyrolactone, γ-butyrolactone, δ-valerolactone, ε-caprolactone, 1,5-dioxepan-2-one, pivalolactone and 1,4-dioxane-2-one.

4. The composition of claim 1 , wherein the degradable polyester aliphatic comprises aliphatic polycarbonate segments within the A and A′ chains in the A-B-A′ structure.

5. The composition according to claim 1 , wherein the at least one polymer having the structure A-B-′ is chain extended with a diisocyanate compound to form a polyesterurethane.

6. The composition according to claim 1 , wherein the at least one polymer having the structure A-B-A′ is end-capped with a monofunctional isocyanate compound.

7. The composition of claim 1 , wherein the at least one polymer having the structure A-B-A′ is reacted with an excess of diisocyanate to form a reactive polyesterurethane prepolymer.

8. The composition of claim 7 , wherein the reactive polyesterurethane prepolymer is reacted with water or a multifunctional chain extender group selected from the group consisting of an amino, hydroxyl, and thiol compound to generate a polyesterurethaneurea, polyesterurethane, or polyesterurethanethiourethane polymer.

9. The composition of claim 1 , further comprising a bioactive agent.

10. The composition of claim 1 , wherein the composition is in the form of a film.

11. The composition of claim 1 , wherein the composition is in the form of a porous construct.

12. A composition comprising:
at least one polymer having the structure A-B-A′, wherein A and A′ may be the same or different and each is a degradable polyester component and wherein B is the reaction product resulting from the reaction between (i) A and A′ and (ii) a diol, having one or more pendant oligomeric or polymeric groups, said at least one polymer being selected from the group consisting of the following:

wherein X is O, S, or —CH2-,
Y is C or N,
R1 is H, an alkyl group containing 1-24 carbon atoms, a group containing an aromatic substituent or a group containing multiple alkylene oxide units of up to 500 units,
R2 is alkyl group containing 1-12 carbon atoms,
R3 is H, an alkyl group containing 1-24 carbon atoms, or an alkoxy group containing multiple alkylene oxide units of up to 500 units,
n is 1-12,
a is 2-500, and
b is 1-100;

wherein X is O, S, or —CH2-,
Y is C or N,
R1 is H, an alkyl group containing 1-24 carbon atoms, a group containing an aromatic substituent or a group containing multiple alkylene oxide units of up to 500 units,
R2 is alkyl group containing 1-12 carbon atoms,
R3 is H, an alkyl group containing 1-24 carbon atoms, or an alkoxy group containing multiple alkylene oxide units of up to 500 units,
R4 is a diisocyanate reaction fragment,
n is 1-12,
a is 2-500,
b is 1-100, and
c is 1-200;

wherein X is O, S, or —CH2-,
Y is C or N,
R1 is H, an alkyl group containing 1-24 carbon atoms, a group containing an aromatic substituent or a group containing multiple alkylene oxide units of up to 500 units,
R2 is alkyl group containing 1-12 carbon atoms or a silicone containing fragment,
R3 is H, an alkyl group containing 1-24 carbon atoms, or an alkoxy group containing multiple alkylene oxide units of up to 500 units,
R4 is a diisocyanate reaction fragment,
n is 1-12,
a is 2-500,
b is 1-100,
c is 1-200, and
d is 4-300;

wherein X is O, S, or —CH2-,
Y is C or N,
Z is O, S, NH, or an N-alkyl group,
R1 is H, an alkyl group containing 1-24 carbon atoms, a group containing an aromatic substituent or a group containing multiple alkylene oxide units of up to 500 units,
R2 is alkyl group containing 1-12 carbon atoms,
R3 is H, an alkyl group containing 1-24 carbon atoms, or an alkoxy group containing multiple alkylene oxide units of up to 500 units,
R4 is a diisocyanate reaction fragment,
R5 is an alkyl, silicone, alicyclic, heterocyclic, or an aromatic group,
n is 1-12,
a is 2-500,
b is 1-100,
c is 1-20, and
d is 4-300;

wherein X is O, S, or —CH2-,
Y is C or N,
R1 is H or an alkyl group containing 1-24 carbon atoms, a group containing an aromatic substituent or a group containing multiple alkylene oxide units of up to 500 units,
R2 is alkyl group containing 1-12 carbon atoms or a silicone containing fragment,
R3 is H, an alkyl group containing 1-24 carbon atoms, or an alkoxy group containing multiple alkylene oxide units of up to 500 units,
a is 2-500,
b is 1-100, and
d is 4-300.

13. The composition according to claim 12 , wherein the alkylene oxide unit is a poly(ethylene oxide) unit.

Assignees

• Parakka James
• Iyer Ananth
• Dsm Ip Assets Bv

Inventors

• Parakka James
• Iyer Ananth

Classifications

• A61P43/00

  Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 · CPC title

• A61L31/148

  Materials at least partially resorbable by the body · CPC title

• A61L15/58

  Adhesives · CPC title

• A61L15/22

  containing macromolecular materials · CPC title

• A61L15/64

  specially adapted to be resorbable inside the body · CPC title