Delivery of hydrophobic active agent particles

Patent metadata

Field	Value
Publication number	US-11529440-B2
Application number	US-202016847272-A
Country	US
Kind code	B2
Filing date	Apr 13, 2020
Priority date	May 20, 2011
Publication date	Dec 20, 2022
Grant date	Dec 20, 2022

Abstract

Embodiments of the invention include drug delivery coatings and devices including the same. In an embodiment, the invention includes a drug delivery coating including a polymeric layer. The polymeric layer can include a hydrophilic outer surface. The coating can also include a matrix contacting the hydrophilic outer surface. The matrix can include a particulate hydrophobic therapeutic agent and a cationic agent. The polymeric layer can further include a hydrophilic polymer having pendent photoreactive groups and a photo-crosslinker including two aryl ketone functionalities. Other embodiments are also included herein.

First claim

The invention claimed is:

1. A drug delivery coating comprising
a base polymeric layer, the base polymeric layer comprising a hydrophilic surface and a photo-crosslinker comprising at least two aryl ketone functionalities;
a therapeutic agent layer forming an exterior surface the drug delivery coating, the therapeutic agent layer contacting the hydrophilic surface of the base polymeric layer and having a composition different than the base polymeric layer, the therapeutic agent layer comprising
a particulate hydrophobic therapeutic agent; and
a cationic agent, the cationic agent comprising polyethyleneimine (PEI);
wherein a ratio (wt./wt.) of particulate hydrophobic therapeutic agent to the cationic agent is about 99.9/0.1 to 90/10.

2. The drug delivery coating of claim 1 , wherein the ratio (wt./wt.) of particulate hydrophobic therapeutic agent to the cationic agent is about 99.9/0.1 to 95/5.

3. The drug delivery coating of claim 1 , wherein the ratio (wt./wt.) of particulate hydrophobic therapeutic agent to the cationic agent is about 99.9/0.1 to 98/2.

4. The drug delivery coating of claim 1 , wherein the ratio (wt./wt.) of particulate hydrophobic therapeutic agent to the cationic agent is about 99.9/0.1 to 99/1.

5. The drug delivery coating of claim 1 , the cationic agent comprising a polyethyleneimine (PEI) homopolymer or copolymer.

6. The drug delivery coating of claim 5 , the copolymer comprising a PEG block.

7. The drug delivery coating of claim 5 , the copolymer selected from the group consisting of PEG-PEI and PLGA-PEI.

8. The drug delivery coating of claim 1 , wherein the photo-crosslinker is chosen from ethylenebis(4-benzoylbenzyldimethylammonium) dibromide and bis(4-benzoyl)phosphate sodium salt.

9. The drug delivery coating of claim 1 , wherein the base polymeric layer comprises a hydrophilic polymer having pendent photoreactive groups.

10. The drug delivery coating of claim 9 , the hydrophilic polymer having pendent photoreactive groups comprising a photo-polyacrylamide.

11. The drug delivery coating of claim 10 , wherein the photo-polyacrylamide is chosen from poly(N-3-aminopropyl)methacrylamide-co-N-(3-(4-benzoylbenzamido)propyl)methacrylamide; poly(acrylamide-co-N-(3-(4-benzoylbenzamido)propyl)methacylamide), poly(acrylamide-co-maleic-6-aminocaproic acid-N-oxysuccinimide-co-N-(3-(4-benzoylbenzamido)propyl)methacrylamide) and poly(acrylamide-co-(3-(4-benzoylbenzamido)propyl)methacrylamide)-co-glycidylmethacrylate.

12. The drug delivery coating of claim 10 , wherein the photo-polyacrylamide is poly(N-3-aminopropyl)methacrylamide-co-N-(3-(4-benzoylbenzamido)propyl) methacrylamide.

13. The drug delivery coating of claim 10 , wherein the photo-polyacrylamide is poly(N-3-aminopropyl)methacrylamide-co-N-(3-(4-benzoylbenzamido)propyl)methacrylamide and the photo crosslinker is ethylenebis(4-benzoylbenzyldimethylammonium) dibromide.

Assignees

• Surmodics Inc

Inventors

• Slager Joram
• Heyer Toni M
• Babcock David E

Classifications

• A61K9/5031

  obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, poly(lactide-co-glycolide) · CPC title

• A61M2025/105

  having a balloon suitable for drug delivery, e.g. by using holes for delivery, drug coating or membranes · CPC title

• A61L2420/08

  Coatings comprising two or more layers · CPC title

• A61L2300/258

  Genetic materials, DNA, RNA, genes, vectors, e.g. plasmids · CPC title

• A61K31/713

  Double-stranded nucleic acids or oligonucleotides · CPC title