IP Library Granted Patent US 11,529,440
Granted Patent B2
US 11,529,440 · App. 16/847,272 · Granted Dec 20, 2022

Delivery of hydrophobic active agent particles

Inventors: Joram Slager (St. Louis Park, MN); Toni M. Heyer (St. Louis Park, MN); David E. Babcock (Brooklyn Park, MN)
Assignee: Surmodics, Inc.
A61L29/085A61K31/337A61K31/713A61K47/34A61L29/14A61L29/16A61M25/10C12N15/113A61K9/5031A61L2300/258A61L2300/416A61L2300/606A61L2300/608A61L2300/62A61L2300/802A61L2420/06A61L2420/08A61M2025/105C12N2310/14C12N2320/32
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Quick Facts
Patent No.
US 11,529,440
App. No.
16/847,272
Granted
Dec 20, 2022
Kind
B2
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.

Claims (18)

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.

Assignments (4)
SECURITY INTEREST Recorded Jan 21, 2026
From: SURMODICS MD, LLC
To: BANK OF MONTREAL, AS COLLATERAL AGENT
Reel/Frame 074461/0199 →
RELEASE OF SECURITY INTEREST Recorded Nov 24, 2025
From: MIDCAP FUNDING IV TRUST
To: SURMODICS, INC.; SURMODICS SHARED SERVICES, LLC; SURMODICS HOLDINGS, LLC; SURMODICS COATINGS, LLC; SURMODICS MD, LLC; SURMODICS COATINGS MFG, LLC; SURMODICS IVD, INC.; SURMODICS MD OPERATIONS, LLC; NORMEDIX, INC.
Reel/Frame 073690/0186 →
SECURITY INTEREST Recorded Aug 23, 2024
From: SURMODICS, INC.; SURMODICS SHARED SERVICES, LLC; SURMODICS HOLDINGS, LLC; SURMODICS COATINGS, LLC; SURMODICS MD, LLC; SURMODICS COATINGS MFG, LLC; SURMODICS IVD, INC.; SURMODICS MD OPERATIONS, LLC; NORMEDIX, INC.
To: MIDCAP FUNDING IV TRUST
Reel/Frame 068762/0423 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 29, 2020
From: SLAGER, JORAM; HEYER, TONI M.; BABCOCK, DAVID
To: SURMODICS, INC.
Reel/Frame 054209/0526 →
Continuity (6)
Continuation 15850010 · Dec 21, 2017
Continuation 14609270 · Jan 29, 2015
Continuation In Part 13793390 · Mar 11, 2013
Continuation In Part 13469844 · May 11, 2012
Provisional Application 61488582 · May 20, 2011
Related Publication 20200237971A1 · Jul 30, 2020