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

• US 10,328,183 B2
• Filed: 06/06/2018
• Issued: 06/25/2019
• 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:
  US16/001,514
• Publication Number:
  US 20180280590A1
• Time in Patent Office: 384 Days
• Field of Search: None
• 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 composition comprising:

a cream, paste, or gel comprising a gallate containing compound and a drug, wherein the gallate containing compound is tannic acid.

2. The composition of claim 1, wherein the drug is amphotericin.

3. The composition of claim 1, comprising a cream comprising the gallate containing compound and the drug.

4. The composition of claim 1, comprising a paste comprising the gallate containing compound and the drug.

5. The composition of claim 1, wherein the gallate containing compound is present is an amount effective in increasing the cellular uptake of the drug.

6. The composition of claim 1, wherein the gallate containing compound is present is an amount effective in increasing the solubility of the drug in an aqueous medium.

7. The composition of claim 1, wherein the gallate containing compound and the drug are contained within a matrix of a polymeric microparticle, and wherein the drug is a water-insoluble therapeutic agent.

8. The composition of claim 7, wherein the polymeric matrix comprises a biodegradable polymer.

9. The composition of claim 7, wherein the polymeric matrix comprises a non-biodegradable polymer.

10. The composition of claim 7, wherein the gallate containing compound and the water-insoluble therapeutic agent are present at a weight ratio of between 1 to 40 and 500 to 1 gallate containing compound to water-insoluble therapeutic agent.

16. The composition of claim 1, wherein the drug is selected from the group consisting of paclitaxel, docetaxel, a paclitaxel analog, or a paclitaxel derivative or other taxane compound;

a macrolide immunosuppressive agent, sirolimus, pimecrolimus, tacrolimus, everolimus, zotarolimus, novolimus, myolimus, temsirolimus, deforolimus, biolimus, an antiproliferative agent;

a smooth muscle cell inhibitor; and

an inhibitor of the mammalian target of rapamycin (mTOR inhibitor).

17. The composition of claim 16, wherein the drug is paclitaxel.

18. The composition of claim 16, wherein the drug is selected from the group consisting of sirolimus, pimecrolimus, tacrolimus, everolimus, zotarolimus, novolimus, myolimus, temsirolimus, deforolimus, and biolimus.

19. The composition of claim 18, wherein the drug is sirolimus.

11. A composition comprising:

an aqueous solvent;

a gallate containing compound; and

water-insoluble therapeutic agent,

wherein the gallate containing compound is tannic acid.

12. The composition of claim 11, wherein the aqueous solvent is selected from the group consisting of saline and water.

13. The composition of claim 11, wherein the gallate containing compound is present in an amount that increases the solubility of a water-insoluble therapeutic agent in the composition by 10, 20, 30, 40, 50 75, 100, 125, 150, 200, 300 or 400 percentage compared to an otherwise identical composition that does not include the gallate containing compound.

14. The composition of claim 11, wherein the water-insoluble therapeutic agent is selected from the group consisting of paclitaxel, docetaxel, a paclitaxel analog, or a paclitaxel derivative or other taxane compound;

a macrolide immunosuppressive agent, sirolimus, pimecrolimus, tacrolimus, everolimus, zotarolimus, novolimus, myolimus, temsirolimus, deforolimus, or biolimus;

an antiproliferative agent;

a smooth muscle cell inhibitor; and

an inhibitor of the mammalian target of rapamycin (mTOR inhibitor).

15. The composition of claim 11, wherein the water-insoluble therapeutic agent is selected from the group consisting of antiproliferative agents immunosuppressive agents, restenosis-inhibiting agents, anti-cancer agents, analgesics/antipyretics, anesthetics, antiasthmatics, antibiotics, antidepressants, antidiabetics, antifungal agents, antihypertensive agents, anti-inflammatories, antineoplastics, antianxiety agents, sedatives/hypnotics, antianginal agents, nitrates, antipsychotic agents, antimanic agents, antiarrhythmics, antiarthritic agents, antigout agents, thrombolytic agents, hemorheologic agents, anticonvulsants, antihistamines, agents useful for calcium regulation, antibacterial agents, antiviral agents, antimicrobials, anti-infectives, bronchodilators, steroids and hormones.