Compositions and devices incorporating water-insoluble therapeutic agents and methods of the use thereof

• US 9,572,914 B2
• Filed: 10/12/2015
• Issued: 02/21/2017
• Est. Priority Date: 08/07/2014
• Status: Active Grant

• Current Assignee: Cook Medical Incorporated (Cook Group Incorporated)
• Original Assignee: Cook Medical Incorporated (Cook Group Incorporated)
• Inventors: Jackson, John, Machan, Lindsay Stuart, Letchford, Kevin
• Primary Examiner(s): Wax, Robert A
• Assistant Examiner(s): MERCIER, MELISSA S
• Application Number:
  US14/880,332
• Publication Number:
  US 20160129161A1
• Time in Patent Office: 498 Days
• Field of Search: None
• US Class Current: 1/1
• CPC Class Codes: A61K 31/337 having four-membered rings, e.g. taxol
• CPC Class Codes: A61K 31/353 3,4-Dihydrobenzopyrans, e.g. chroman, catechin
• CPC Class Codes: A61K 31/436 the heterocyclic ring system containing a six-membered ring having oxygen as a ring hetero atom, e.g. rapamycin
• CPC Class Codes: A61K 31/58 containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin digitoxin A61K31/7048
• CPC Class Codes: A61L 2300/416 Anti-neoplastic or anti-proliferative or anti-restenosis or anti-angiogenic agents, e.g. paclitaxel, sirolimus
• CPC Class Codes: A61L 2300/426 Immunomodulating agents, i.e. cytokines, interleukins, interferons
• CPC Class Codes: A61L 2300/602 Type of release, e.g. controlled, sustained, slow
• CPC Class Codes: A61L 2300/606 Coatings
• CPC Class Codes: A61L 2300/61 containing two or more active agents in different layers
• CPC Class Codes: A61L 2420/06 Coatings containing a mixture of two or more compounds
• CPC Class Codes: A61L 27/34 Macromolecular materials
• CPC Class Codes: A61L 27/44 having a macromolecular matrix
• CPC Class Codes: A61L 27/54 Biologically active materials, e.g. therapeutic substances A61L27/227 takes precedence
• CPC Class Codes: A61L 29/08 Materials for coatings
• CPC Class Codes: A61L 29/085 Macromolecular materials
• CPC Class Codes: A61L 29/16 Biologically active materials, e.g. therapeutic substances A61L29/048 takes precedence
• CPC Class Codes: A61L 31/08 Materials for coatings
• CPC Class Codes: A61L 31/10 Macromolecular materials
• CPC Class Codes: A61L 31/16 Biologically active materials, e.g. therapeutic substances A61L31/047 takes precedence
• CPC Class Codes: A61M 2025/105 having a balloon suitable for drug delivery, e.g. by using holes for delivery, drug coating or membranes
• CPC Class Codes: A61M 25/09 : Guide wires
• CPC Class Codes: A61M 25/10 : Balloon catheters A61M25/0125 takes precedence; embolectomy A61B17/22032; retractors A61B17/02; inflatable balloons for placing stents or stent-grafts A61F2/958 ; stomach balloons for treatment of obesity A61F5/0003; oesophagal tubes A61J15/00
• CPC Class Codes: A61P 11/06 : Antiasthmatics
• CPC Class Codes: A61P 19/02 : for joint disorders, e.g. arthritis, arthrosis
• CPC Class Codes: A61P 25/00 : Drugs for disorders of the nervous system
• CPC Class Codes: A61P 27/02 : Ophthalmic agents
• CPC Class Codes: A61P 35/00 : Antineoplastic agents
• CPC Class Codes: H05K 999/99 : dummy group

Abstract

Various aspects of the present invention provide compositions and implantable devices including a water-insoluble therapeutic agent solubilized in a matrix of a gallate-containing compound. Other aspects provide methods of manufacturing and using such compositions and devices

Claims

1. A medical device comprising:

a base structure having a surface, and

a coating on the surface comprising a water-insoluble therapeutic agent solubilized within a matrix of gallate-containing compound, wherein the coating is free of a polymeric carrier and wherein the coating adheres directly to the base structure and forms an outermost surface of the medical device.

2. The medical device of claim 1, wherein the coating is free of a non-polymer carrier modifying a rate of release of the therapeutic agent.

3. The medical device of claim 1, wherein the gallate containing compound is selected from a group consisting of epi gallo catechin gallate, tannic acid and epi catechin gallate.

4. The medical device of claim 1, wherein the gallate containing compound comprises a gallate substituted molecule selected from the group consisting of a dendrimer, a polymer, a macromolecule or a small molecule.

5. The medical device of claim 3, wherein the gallate containing compound is epi gallo catechin gallate.

6. The medical device of claim 1, wherein the gallate containing compound and the water-insoluble therapeutic agent are present at a weight ratio of between 30 to 1 and 500 to 1 gallate containing compound to water-insoluble therapeutic agent.

7. The medical device of claim 6, wherein the water-insoluble therapeutic agent is contained within a matrix of the gallate containing compound and wherein the water-insoluble therapeutic agent and the gallate containing compound are present at a weight ratio of between 30 to 1 and 100 to 1 gallate containing compound to water-insoluble therapeutic agent.

8. The medical device of claim 1, wherein the implantable medical device is an expandable balloon or a stent.

9. The medical device of claim 1, wherein the medical device is selected from the group consisting of a stent, a vascular stent, a ureteral stent, a catheter, a balloon, a balloon catheter, a stent graft, a wire guide, and a cannula.

10. The medical device of claim 1, wherein the water-insoluble therapeutic agent is an immunosuppressive agent, an antiproliferative agent, a microtubule stabilizing agent, a restenosis-inhibiting agent, or an inhibitor of the mammalian target of rapamycin.

11. The medical device of claim 10, wherein the water-insoluble therapeutic agent is a taxane compound.

12. The medical device of claim 11, wherein the taxane compound is paclitaxel or docetaxel.

13. The medical device of claim 12, wherein the therapeutic agent is a macrolide immunosuppressive agent.

14. The medical device of claim 1, wherein the coating consists essentially of the water-insoluble therapeutic agent and the gallate containing compound.

17. The medical device of claim 1, wherein the base structure is a balloon.

15. A medical device comprising:

a base structure comprising a balloon or a stent, and

a coating on the base structure comprising a gallate containing compound and a taxane agent, wherein the gallate containing compound and the taxane agent are present at a weight ratio of between 1 to 40 and 500 to 1 gallate containing compound to taxane agent wherein the coating is free of a polymeric carrier and wherein the coating adheres directly to the base structure and forms an outermost surface of the medical device.

16. The medical device of claim 15, wherein taxane agent is paclitaxel or docetaxel.

18. A medical device comprising:

a balloon, and

a coating on the balloon comprising a gallate containing compound and a taxane agent, wherein the taxane agent is solubilized within a matrix of the gallate containing compound, wherein the gallate containing compound and the taxane agent are present at a weight ratio of between 30 to 1 and 100 to 1 gallate containing compound to taxane agent, wherein the coating is free of a polymeric carrier and wherein the coating adheres directly to the balloon and forms an outermost surface of the medical device.