IP Library Granted Patent US 11,873,361
Granted Patent B2
US 11,873,361 · App. 17/836,282 · Granted Jan 16, 2024

Ophthalmic devices

Inventors: Alok Kumar Awasthi (Pittsford, NY); Kristen Rae Hovinga (Honeoye Falls, NY); Emily Abrams Gabriel (Pittsford, NY); Kevin Jacob DeRyke (Webster, NY); Jade J. Russell (Perry, NY); James Anthony DiBella, Jr. (Macedon, NY); Alana Ingham (Hilton, NY)
Assignee: BAUSCH + LOMB IRELAND LIMITED
C08F283/06A61L27/16A61L27/50C08F226/10C08F283/12C08K5/18C08K5/42A61L2430/16G02B1/043
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 11,873,361
App. No.
17/836,282
Filed
Jun 9, 2022
Granted
Jan 16, 2024
Kind
B2
Art Unit
1767
USPC
523/107
Abstract

An ophthalmic device for slowing, inhibiting or preventing myopia progression which is a polymerization product of a monomeric mixture comprising (a) greater than 50 wt. %, based on the total weight of the monomeric mixture, of one or more non-silicone-containing hydrophilic monomers; (b) one or more crosslinking agents; and (c) one or more red-light blocking compounds blocking greater than 5% to about 25% of red-light transmission through the ophthalmic device at a wavelength of from about 550 nm to about 800 nm, wherein the one or more red-light blocking compounds have one or more ethylenically unsaturated reactive end groups.

Claims (50)

1. An ophthalmic device which is a polymerization product of a monomeric mixture comprising:

(a) greater than 50 wt. %, based on the total weight of the monomeric mixture, of one or more non-silicone-containing hydrophilic monomers;

(b) one or more crosslinking agents; and

(c) one or more red-light blocking compounds blocking greater than 5% to about 25% of red-light transmission through the ophthalmic device at a wavelength of from about 550 nanometers (nm) to about 800 nm, wherein the one or more red-light blocking compounds have one or more ethylenically unsaturated reactive end groups.

2. The ophthalmic device according to claim 1 , wherein the one or more non-silicone-containing hydrophilic monomers are selected from the group consisting of an unsaturated carboxylic acid, an acrylamide, a vinyl lactam, a poly(alkyleneoxy)(meth)acrylate, (meth)acrylic acid, a hydroxyl-containing-(meth)acrylate, a hydrophilic vinyl carbonate, a hydrophilic vinyl carbamate monomer, a hydrophilic oxazolone monomer, and mixtures thereof.

3. The ophthalmic device according to claim 1 , wherein the one or more non-silicone-containing hydrophilic monomers are selected from the group consisting of N,N-dimethylacrylamide, N,N-dimethylmethacrylamide, N-vinyl-2-pyrrolidone, N-vinyl caprolactam, N-vinyl-2-piperidone, 2-hydroxyethyl methacrylate, N-(2-hydroxyethyl)methacrylamide, glyceryl methacrylate, N-methacryloyl glycine, (2-hydroxy-3-methacryloylpropyl)-4-methoxy phenyl ether and mixtures thereof.

4. The ophthalmic device according to claim 1 , wherein the one or more crosslinking agents are bi- or polyfunctional crosslinking agents comprising two or more reactive functional groups.

5. The ophthalmic device according to claim 1 , wherein the one or more red-light blocking compounds comprise one or more red-light blocking compounds blocking greater than about 5% to about 25% of red-light transmission through the ophthalmic device at a wavelength of from about 550 nm to about 700 nm, wherein the one or more red-light blocking compounds have one or more ethylenically unsaturated reactive end groups.

6. The ophthalmic device according to claim 1 , wherein the one or more red-light blocking compounds comprise one or more red-light blocking compounds blocking greater than about 5% to about 25% of red-light transmission through the ophthalmic device at a wavelength of from about 650 nm to about 680 nm, wherein the one or more red-light blocking compounds have one or more ethylenically unsaturated reactive end groups.

7. The ophthalmic device according to claim 1 , wherein the one or more red-light blocking compounds comprise one or more red-light blocking compounds blocking from about 10% to about 15% of red-light transmission through the ophthalmic device at a wavelength of from about 550 nm to about 800 nm, wherein the one or more red-light blocking compounds have one or more ethylenically unsaturated reactive end groups.

8. The ophthalmic device according to claim 1 , wherein the one or more red-light blocking compounds comprise one or more red-light blocking compounds blocking from about 10% to about 15% of red-light transmission through the ophthalmic device at a wavelength of from about 550 nm to about 700 nm, wherein the one or more red-light blocking compounds have one or more ethylenically unsaturated reactive end groups.

9. The ophthalmic device according to claim 1 , wherein the one or more red-light blocking compounds comprise one or more red-light blocking compounds blocking greater from about 10% to about 15% of red-light transmission through the ophthalmic device at a wavelength of from about 650 nm to about 680 nm, wherein the one or more red-light blocking compounds have one or more ethylenically unsaturated reactive end groups.

10. The ophthalmic device according to claim 1 , wherein the one or more ethylenically unsaturated reactive end groups of the one or more red-light blocking compounds comprise one or more (meth)acrylate end groups.

11. The ophthalmic device according to claim 1 , wherein the one or more ethylenically unsaturated reactive end groups are represented by the following structure:

wherein R* is a linking group or bond.

12. The ophthalmic device according to claim 1 , wherein the one or more red-light blocking compounds are represented by the following structure:

wherein R 1 and R 2 are hydrogen or a methacrylate-containing reactive end group, with at least one of R 1 and R 2 being a methacrylate-containing reactive end group; and R 3 is hydrogen or a sulfonate group.

13. The ophthalmic device according to claim 1 , wherein the one or more red-light blocking compounds are represented by the following structure:

wherein R 1 and R 2 are hydrogen or an ethylenically unsaturated reactive end group, with at least one of R 1 and R 2 being an ethylenically unsaturated reactive end group; and R 3 and R 4 are independently hydrogen or a sulfonate group.

14. The ophthalmic device according to claim 1 , wherein the monomeric mixture comprises:

(a) greater than 50 wt. % and up to 90 wt. %, based on the total weight of the monomeric mixture, of the one or more non-silicone-containing hydrophilic monomers;

(b) about 0.1 to about 2.0 wt. %, based on the total weight of the monomeric mixture, of the one or more crosslinking agents; and

(c) about 0.02 to about 0.3 wt. %, based on the total weight of the monomeric mixture, of the one or more red-light blocking compounds.

15. The ophthalmic device according to claim 1 , wherein the monomeric mixture further comprises one or more non-bulky organosilicon-containing monomers comprising a compound represented by the following structure:

wherein L is ethylenically unsaturated polymerizable group, V is a linker group or a bond; R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are independently hydrogen, an alkyl group, a haloalkyl group, a cycloalkyl group, a heterocycloalkyl group, an alkenyl group, a halo alkenyl group, or an aromatic group; R 10 and R 11 are independently hydrogen or alkyl group wherein at least one of R 10 and R 11 is hydrogen; y is 2 to 7 and n is 1 to 100, or a compound represented by the following structure:

wherein R 12 is H or methyl; X is O or NR 16 ; wherein R 16 is hydrogen or C 1 to C 4 alkyl, which may be further substituted with one or more hydroxyl groups; R 13 is a divalent alkyl group, which may further be functionalized with a group selected from the group consisting of an ether group, a hydroxyl group, a carbamate group and combinations thereof; each R 14 is independently a phenyl or C 1 to C 4 alkyl which may be substituted with fluorine, hydroxyl or an ether; R 15 is a C 1 to C 4 alkyl; and a is 2 to 50.

16. The ophthalmic device according to claim 1 , wherein the monomeric mixture further comprises one or more bulky siloxane monomers represented by the following structure:

wherein X denotes —O— or —NR 19 — where each R 19 is hydrogen or a C 1 -C 4 alkyl; R 17 independently denotes hydrogen or methyl; each R 18 independently denotes a C 1 -C 6 alkyl radical, a phenyl radical or a group represented by the following structure:

wherein each R 18′ independently denotes a C 1 -C 6 alkyl radical or a phenyl radical; and h is 1 to 10;

or the following structure:

wherein X denotes —NR 19 —; wherein R 19 denotes hydrogen or a C 1 -C 4 alkyl; R 17 denotes hydrogen or methyl; each R 18 independently denotes a C 1 -C 6 alkyl radical, a phenyl radical or a group represented by the following structure:

wherein each R 18′ independently denotes a C 1 -C 6 alkyl radical or a phenyl radical; and h is 1 to 10.

17. The ophthalmic device according to claim 1 , which is a contact lens or an intraocular lens.

18. A method of making an ophthalmic device, the method comprising:

(a) providing a monomeric mixture comprising:

(i) greater than 50 wt. %, based on the total weight of the monomeric mixture, of one or more non-silicone-containing hydrophilic monomers;

(ii) one or more crosslinking agents; and

(iii) one or more red-light blocking compounds blocking greater than about 5% to about 25% of red-light transmission through the ophthalmic device at a wavelength of from about 550 nanometers (nm) to about 800 nm, wherein the one or more red-light blocking compounds have one or more ethylenically unsaturated reactive end groups;

(b) subjecting the monomeric mixture to polymerizing conditions to provide a polymerized ophthalmic device, and

(c) hydrating the polymerized ophthalmic device.

19. The method according to claim 18 , wherein the monomeric mixture comprises:

(i) greater than 50 wt. % and up to 90 wt. %, based on the total weight of the monomeric mixture, of the one or more non-silicone-containing hydrophilic monomers;

(ii) about 0.1 to about 2.0 wt. %, based on the total weight of the monomeric mixture, of the one or more crosslinking agents; and

(iii) about 0.02 to about 0.3 wt. %, based on the total weight of the monomeric mixture, of the one or more red-light blocking compounds.

20. A method for slowing, inhibiting or preventing myopia progression in a subject in need thereof, the method comprising:

(a) providing an ophthalmic device which is a polymerization product of a monomeric mixture comprising:

(i) greater than 50 wt. %, based on the total weight of the monomeric mixture, of one or more non-silicone-containing hydrophilic monomers;

(ii) one or more crosslinking agents; and

(iii) one or more red-light blocking compounds blocking greater than about 5% to about 25% of red-light transmission through the ophthalmic device at a wavelength of from about 550 nanometers (nm) to about 800 nm, wherein the one or more red-light blocking compounds have one or more ethylenically unsaturated reactive end groups; and

(b) inserting the ophthalmic device into an eye of the subject.

Assignments (2)
ASSIGNMENT OF SECURITY INTEREST IN PATENTS PREVIOUSLY RECORDED AT REEL/FRAME (065709/0253) Recorded Aug 14, 2025
From: CITIBANK, N.A., AS RESIGNING AGENT
To: JPMORGAN CHASE BANK, N.A., AS SUCCESSOR AGENT
Reel/Frame 072460/0691 →
PATENT SECURITY AGREEMENT Recorded Jul 1, 2025
From: BAUSCH & LOMB INCORPORATED; ALDEN OPTICAL LABORATORIES, INC.; BAUSCH + LOMB IRELAND LIMITED
To: CITIBANK, N.A., AS NOTES COLLATERAL AGENT
Reel/Frame 071773/0871 →