Granted Patent B2

US 11,820,899 · App. 17/110,443 · Granted Nov 21, 2023

Inventors: Shivkumar Mahadevan (Jacksonville, FL); Dawn D. Wright (St. Augustine, FL)

Assignee: Johnson & Johnson Vision Care, Inc.

C09B62/465A61L27/00C08F230/08C08L77/00C08L83/04G02B1/04G02B1/043G02C7/04G02C7/10C08K5/1545C08K5/45

Abstract

Claims (59)

1. A method for making an ophthalmic device, the method comprising:

(a) providing a reactive mixture containing one or more device forming monomers, a radical initiator, and a compound of formula I:

wherein:

m and n are independently 0, 1, 2, 3, or 4;

T is a bond, O, or NR;

X is O, S, NR, SO, or SO 2 ;

Y is a linking group;

P g is a polymerizable group;

R at each occurrence is independently H, C 1 -C 6 alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, or Y—P g ;

R 1 and R 2 , when present, are independently at each occurrence C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 thioalkyl, C 3 -C 7 cycloalkyl, aryl, halo, hydroxy, amino, NR 3 R 4 , or benzyl, wherein R 3 and R 4 are independently H or C 1 -C 6 alkyl, or two adjacent R 1 or R 2 groups, together with the carbon atoms to which they are attached, combine to form a cycloalkyl or aryl ring; and

EWG is an electron withdrawing group; and

(b) polymerizing the reactive mixture to form the ophthalmic device.

2. The method of claim 1 wherein m and n are each independently 0 or 1.

3. The method of claim 1 wherein Y at each occurrence is independently alkylene, cycloalkylene, heterocycloalkylene, arylene, heteroarylene, oxaalkylene, alkylene-amide-alkylene, alkylene-amine-alkylene, or combinations thereof.

4. The method of claim 1 wherein P g comprises styryl, vinyl carbonate, vinyl ether, vinyl carbamate, N-vinyl lactam, N-vinylamide, (meth)acrylate, or (meth)acrylamide.

5. The method of claim 1 wherein X is O.

6. The method of claim 1 wherein X is S.

7. The method of claim 1 wherein EWG is cyano, amide, ester, keto, or aldehyde.

8. The method of claim 1 wherein EWG is cyano.

9. The method of claim 1 that is:

2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate;

2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl acrylate;

N-(2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl)methacrylamide;

N-(2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl)acrylamide;

2-(2-cyano-N-methyl-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate;

2-cyano-2-(9H-thioxanthen-9-ylidene)-N-(2-(N-vinylacetamido)ethyl)acetamide;

2-(2-cyano-2-(9H-xanthen-9-ylidene)acetamido)ethyl methacrylate;

2-(2-cyano-2-(9H-xanthen-9-ylidene)acetamido)ethyl acrylate;

N-(2-(2-cyano-2-(9H-xanthen-9-ylidene)acetamido)ethyl)methacrylamide;

N-(2-(2-cyano-2-(9H-xanthen-9-ylidene)acetamido)ethyl)acrylamide;

2-(2-cyano-N-methyl-2-(9H-xanthen-9-ylidene)acetamido)ethyl methacrylate;

2-cyano-N-(2-(N-vinylacetamido)ethyl)-2-(9H-xanthen-9-ylidene)acetamide;

2-(2-(acridin-9(10H)-ylidene)-2-cyanoacetamido)ethyl acrylate;

N-(2-(2-(acridin-9(10H)-ylidene)-2-cyanoacetamido)ethyl)methacrylamide;

N-(2-(2-(acridin-9(10H)-ylidene)-2-cyanoacetamido)ethyl)acrylamide;

2-(2-(acridin-9(10H)-ylidene)-2-cyano-N-methylacetamido)ethyl methacrylate;

2-(acridin-9(10H)-ylidene)-2-cyano-N-(2-(N-vinylacetamido)ethyl)acetamide;

2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)-2-methylpropyl methacrylate;

2-(2-cyano-2-(9H-xanthen-9-ylidene)acetoxy)-2-methylpropyl acrylate;

(Z)-2-(2-cyano-2-(3-hydroxyacridin-9(10H)-ylidene)acetamido)ethyl methacrylate;

2-(2-cyano-2-(10-methylacridin-9(10H)-ylidene)acetamido)ethyl methacrylate;

2-(2-cyano-2-(3,6-dihydroxyacridin-9(10H)-ylidene)acetamido)ethyl methacrylate;

(E)-2-(2-(7H-benzo[c]xanthen-7-ylidene)-2-cyanoacetamido)ethyl methacrylate;

(Z)-2-(2-cyano-2-(3-methoxy-9H-xanthen-9-ylidene)acetamido)ethyl methacrylate;

2-(2-cyano-2-(3,6-dihydroxy-9H-xanthen-9-ylidene)acetamido)ethyl methacrylate;

(E)-2-(2-cyano-2-(2-methyl-9H-xanthen-9-ylidene)acetamido)ethyl methacrylate;

(E)-2-(2-cyano-2-(1-hydroxy-9H-xanthen-9-ylidene)acetamido)ethyl methacrylate;

(E)-2-(2-cyano-2-(2,4-dichloro-9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate;

(E)-2-(2-(2-chloro-9H-thioxanthen-9-ylidene)-2-cyanoacetamido)ethyl methacrylate;

(E)-2-(2-cyano-2-(2-isopropyl-9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate;

(E)-2-(2-cyano-2-(4-isopropyl-9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate;

2-(3-oxo-2-(9H-thioxanthen-9-ylidene)propanamido)ethyl methacrylate;

2-(3-oxo-2-(9H-thioxanthen-9-ylidene)butanamido)ethyl methacrylate;

2-(3-methoxy-3-oxo-2-(9H-thioxanthen-9-ylidene)propanamido)ethyl methacrylate;

2-(3-amino-3-oxo-2-(9H-thioxanthen-9-ylidene)propanamido)ethyl methacrylate;

2-(2-cyano-2-(10,10-dioxido-9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate;

N-(2-(2-cyano-2-(10-methylacridin-9(10H)ylidene)acetamido)ethyl) methacrylamide; or

2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetoxy)ethyl methacrylate.

10. The method of claim 1 wherein the Ophthalmic device is a silicone hydrogel contact lens, and wherein the silicone hydrogel contact lens has a contact angle of about 70° or less, a water content of at least 25 percent, and an oxygen permeability of at least 80 barrers.

Continuity (4)

Cited By (10)

US 12,481,173 US 12,486,348 US 12,486,403 US 12,497,379 US 12,509,428 US 12,534,623 US 12,595,370 US 12,595,371 US 12,624,214 US 12,674,032