IP Library Granted Patent US 10,729,820
Granted Patent B2
US 10,729,820 · App. 14/941,446 · Granted Aug 4, 2020

Methods and processes for application of drug delivery polymeric coatings

Inventors: Lisa K. Jennings (Memphis, TN); Jonathan D. McCanless (Memphis, TN); Xiaoping Chen (Germantown, TN); Michael Cole (Boulder, CO)
Assignee: Ariste Medical, LLC
A61L31/10A61L31/08A61L31/16C08F222/10C09D4/00A61L2300/204A61L2300/406A61L2300/606A61L2420/02A61L2420/06C08F222/1025
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Quick Facts
Patent No.
US 10,729,820
App. No.
14/941,446
Granted
Aug 4, 2020
Kind
B2
Abstract

Polymeric coatings, their applications, and the methods of their preparation are described. The coatings may be used to confer desirable properties to the consumer and/or medical products. Also described are methods of loading therapeutic agents on the polymeric coatings and the applications of the drug eluting polymeric coatings thus obtained.

Claims (27)

1. A method of coating a medical device surface, the method comprising:

providing the medical device, said medical device having a microstructure;

exposing a surface of the medical device to a coating formulation comprising:

0.005-80 wt % of a thiol monomer comprising a polythiol;

0.005-80 wt % of an unsaturated monomer, wherein the unsaturated monomer is triallyl isocyanurate or polyethylene glycol dimethacrylate; and

a therapeutic agent; and

inducing polymerization of the coating formulation to obtain a coated device surface that elutes the therapeutic agent.

2. The method of claim 1 , wherein the therapeutic agent is selected from rifampicin, minocycline, minocycline hydrochloride, minocycline hyclate, or any combination thereof.

3. The method of claim 1 , wherein the polythiol comprises pentaerythritol tetrakis(3-mercaptopropionate).

4. The method of claim 1 , wherein the thiol monomer is selected from: glyceryl 1,3-dithioglycolate, glycol dimercaptoacetate, ethoxylated-trimethylolpropan tri(3-mercaptopropionate), trimethylolpropane tris (3-mercaptopropionate), 4-mercaptomethyl-3,6-dithia-1,8-octanedithiol, pentaerythritol tetrakis (3-mercaptoacetate), trimethylolpropane tris (3-mercaptoacetate), 4-t-butyl-1,2-benzenedithiol, bis(2-mercaptoethyl)sulfide, 4,4′-thiodibenzenethiol, benzenedithiol, glycol dimercaptopropionate ethylene bis(3-mercaptopropionate), polythylene glycol dimercaptoacetate, polythylene glycol di(3-mercaptoacetate), (tetrahydrothiophene-2,5-diyl)dimethanethiol, bis(2-mercaptoethyl)sulfide, tris-(3-mercaptopropyl)isocyanurate, 1,2,3-trimercaptopropane, 2,2-bis(mercaptomethyl)-1,3-propanedithiol, 2,5-dimercaptomethyl-4-dithiane, 1,2,4-trimercaptomethyl benzene, 4,8-bis(mercaptomethyl)-3,6,9-trithia-1,11-undecanedithiol, 2-mercaptomethyl-2-methyl-1,3-propanedithiol, 1,8-dimercapto-3,6-dioxaoctane; 2,2′,2″-(2,4,6-trioxo-1,3,5-triazinane-1,3,5-triyl)tris(ethane-2,1-diyl) tris(3-mercaptopropanoate), or any combination thereof.

5. The method of claim 1 , wherein the coating formulation further comprises a radical scavenger selected from hydroquinone, tertbutyl cathetol, or a combination thereof.

6. The method of claim 1 , wherein the polythiol is pentaerythritol tetrakis (3-mercaptoacetate).

7. The method of claim 1 , wherein the polythiol is pentaerythritol tetrakis (3-mercaptoacetate) and the unsaturated monomer is triallyl isocyanurate.

8. The method of claim 1 , wherein the polythiol is pentaerythritol tetrakis (3-mercaptoacetate) and the unsaturated monomer is polyethylene glycol dimethacrylate.

9. The method of claim 1 , further comprising eluting the therapeutic agent from the coated device surface.

10. A method of coating a medical device surface, the method comprising:

providing the medical device, said medical device having a microstructure;

exposing a surface of the medical device to a coating formulation comprising:

0.005-80 wt % of pentaerythritol tetrakis (3-mercaptoacetate); and

0.005-80 wt % of an unsaturated monomer, wherein the unsaturated monomer is triallyl isocyanurate or polyethylene glycol dimethacrylate; and

inducing polymerization of the coating formulation to obtain a coated medical device surface that elutes a therapeutic agent.

11. The method of claim 10 , wherein the coating formulation further comprises the therapeutic agent.

12. The method of claim 10 , further comprising physically assisting the coating formulation to enter the microstructure of the medical device by applying an external force prior to inducing polymerization of the coating formulation.

13. The method of claim 12 , wherein the external force is a negative pressure.

14. The method of claim 12 , wherein the external force is a positive pressure.

15. The method of claim 10 , further comprising exposing the medical device to a solution comprising the therapeutic agent.

16. The method of claim 15 , wherein the exposing of the medical device to the solution comprising the therapeutic agent is performed at a reduced temperature from −50° C. to 0° C.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 16, 2020
From: JENNINGS, LISA K.; MCCANLESS, JONATHAN D.; CHEN, XIAOPING; COLE, MICHAEL
To: ARISTE MEDICAL, INC.
Reel/Frame 052956/0545 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 11, 2017
From: JENNINGS, LISA K.; MCCANLESS, JONATHAN D.; CHEN, XIAOPING; COLE, MICHAEL
To: ARISTE MEDICAL, INC.
Reel/Frame 042345/0883 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 11, 2017
From: AGILE BIOMEDICAL, INC.
To: ARISTE MEDICAL, LLC
Reel/Frame 042346/0124 →
CHANGE OF NAME Recorded May 11, 2017
From: ARISTE MEDICAL, INC.
To: AGILE BIOMEDICAL, INC.
Reel/Frame 042447/0100 →
Continuity (3)
Continuation PCTUS2015027135 · Apr 22, 2015
Provisional Application 61982650 · Apr 22, 2014
Related Publication 20160101219A1 · Apr 14, 2016