IP Library Granted Patent US 10,251,954
Granted Patent B2
US 10,251,954 · App. 15/186,994 · Granted Apr 9, 2019

Hydrogel polymeric compositions and methods

Inventors: Amarpreet S. Sawhney (Lexington, MA); William H. Ransone, II (Waltham, MA)
Assignee: Incept, LLC
A61K47/10A61K9/0019A61K9/0051A61K9/06A61K31/196A61K31/405A61K31/445A61K31/4422A61K31/4458A61K31/496A61K31/573A61K31/58A61K9/0048A61P27/02A61P27/14
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Quick Facts
Patent No.
US 10,251,954
App. No.
15/186,994
Granted
Apr 9, 2019
Kind
B2
Abstract

Some aspects of this disclosure relate to a method of treating an ophthalmic disease affecting an eye of a patient comprising forming a covalently-crosslinked hydrogel for controlled release of a therapeutic agent.

Claims (33)

1. A synthetic, biocompatible polymeric hydrogel for delivering a therapeutic agent to an eye comprising:

a first water soluble synthetic precursor covalently crosslinked to a second water soluble synthetic precursor to form the biocompatible hydrogel,

a hydrophobic steroid small molecule drug in a particulate form free of encapsulating materials, with the steroid being in direct contact with the hydrogel and being releasable from the hydrogel to provide therapy during a period of time in a range from 10 days to 50 days,

wherein any precursors that contribute to form the hydrogel are free of hydrophobic polymeric blocks and provide a molecular weight of 500-10,000 Daltons between crosslinks based on a 1:1 stoichiometric reaction between the first precursor and the second precursor,

wherein the hydrogel is internally covalently crosslinked and is low-swelling, as measurable by the hydrogel having a weight increasing no more than about 50% upon exposure to a physiological solution for twenty-four hours relative to a weight of the hydrogel at the time of formation, and wherein the hydrogel is water-degradable, as measurable by the hydrogel being dissolvable in vitro in an excess of water by degradation of the water-degradable group.

2. The hydrogel of claim 1 wherein the first precursor comprises polyethylene glycol repeats.

3. The hydrogel of claim 1 wherein the first precursor comprises electrophilic functional groups before the crosslinking and the second precursor comprises nucleophilic functional groups before the crosslinking, wherein the first nucleophilic functional groups react with the electrophilic functional groups to covalently crosslink the precursors.

4. The hydrogel of claim 3 wherein the second precursor is dilysine, trilysine, or tetralysine.

5. The hydrogel of claim 1 wherein the first precursor comprises an acrylate-capped polyethylene glycol.

6. The hydrogel of claim 1 wherein the water-degradable group is an ester.

7. The hydrogel of claim 1 wherein the steroid is chosen from the group consisting of triamcinolone, fluorometholone, prednisolone, and loteprednol and their salts or derivatives.

8. The hydrogel of claim 1 wherein the steroid comprises dexamethasone.

9. The hydrogel of claim 1 wherein the steroid is indicated for use in a treatment of ocular inflammation or allergic conjunctivitis.

10. The hydrogel of claim 1 wherein the steroid is indicated for use in a treatment of cystoid macular edema, diabetic macular edema (DME), or diabetic retinopathy.

11. The hydrogel of claim 1 wherein the first precursor comprises poly(ethylene) glycol repeats and the steroid comprises dexamethasone.

12. A synthetic, biocompatible polymeric device for delivering a drug to an eye, the device consisting essentially of

a hydrogel and a drug dispersed in the hydrogel,

the hydrogel comprising a first water soluble synthetic precursor covalently crosslinked to a second water soluble synthetic precursor to form the biocompatible hydrogel,

the drug comprising a hydrophobic steroid small molecule drug in a particulate form free of encapsulating materials, with the steroid being in direct contact with the hydrogel and being releasable from the hydrogel to provide therapy during a period of time in a range from 10 days to 50 days,

wherein any precursors that contribute to form the hydrogel are free of hydrophobic polymeric blocks and provide a molecular weight of 500-10,000 Daltons between crosslinks,

wherein the hydrogel is internally covalently crosslinked and is low-swelling, as measurable by the hydrogel having a weight increasing no more than about 50% upon exposure to a physiological solution for twenty-four hours relative to a weight of the hydrogel at the time of formation, and wherein the hydrogel is water-degradable, as measurable by the hydrogel being dissolvable in vitro in an excess of water by degradation of the water-degradable group.

13. The hydrogel of claim 12 wherein the first precursor comprises polyethylene glycol repeats.

14. The hydrogel of claim 12 wherein the first precursor comprises electrophilic functional groups before the crosslinking and the second precursor comprises nucleophilic functional groups before the crosslinking, wherein the first nucleophilic functional groups react with the electrophilic functional groups to covalently crosslink the precursors.

15. The hydrogel of claim 14 wherein the second precursor is dilysine, trilysine, or tetralysine.

16. The hydrogel of claim 12 wherein the first precursor comprises an acrylate-capped polyethylene glycol.

17. The hydrogel of claim 12 wherein the water-degradable group is an ester.

18. The hydrogel of claim 12 wherein the steroid is chosen from the group consisting of triamcinolone, fluorometholone, prednisolone, and loteprednol and their salts or derivatives.

19. The hydrogel of claim 12 wherein the steroid comprises dexamethasone.

20. The hydrogel of claim 12 wherein the steroid is indicated for use in a treatment of ocular inflammation or allergic conjunctivitis.

21. The hydrogel of claim 12 wherein the steroid is indicated for use in a treatment of cystoid macular edema, diabetic macular edema (DME), or diabetic retinopathy.

22. The hydrogel of claim 12 wherein the first precursor comprises poly(ethylene) glycol repeats and the steroid comprises dexamethasone.

23. The hydrogel of claim 1 wherein the first water soluble synthetic precursor comprises an 8-armed polyethylene glycol having a molecular weight of 15,000.

24. The hydrogel of claim 1 wherein the first water soluble synthetic precursor comprises a polyethylene glycol of 4-16 arms, with the arms having a molecular weight of 1,000-5,000.

Assignments (4)
RELEASE OF SECURITY INTEREST Recorded Aug 4, 2023
From: MIDCAP FINANCIAL TRUST, AS AGENT
To: OCULAR THERAPEUTIX, INC.
Reel/Frame 064497/0294 →
SECURITY INTEREST Recorded Aug 2, 2023
From: OCULAR THERAPEUTIX, INC.
To: BARINGS FINANCE LLC, AS AGENT
Reel/Frame 064476/0368 →
AMENDED AND RESTATED SECURITY INTEREST Recorded Jun 4, 2021
From: OCULAR THERAPEUTIX, INC.
To: MIDCAP FINANCIAL TRUST, AS AGENT
Reel/Frame 057254/0290 →
SECURITY INTEREST Recorded Dec 21, 2018
From: OCULAR THERAPEUTIX, INC.
To: MIDCAP FINANCIAL TRUST, AS AGENT
Reel/Frame 047845/0171 →
Continuity (4)
Continuation 14470081 · Aug 27, 2014
Continuation 12485192 · Jun 16, 2009
Continuation 11825848 · Jul 9, 2007
Related Publication 20160296623A1 · Oct 13, 2016
Cited By (7)
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