Granted Patent B2

US 12,509,428 · App. 16/883,199 · Granted Dec 30, 2025

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

Assignee: Johnson & Johnson Vision Care, Inc.

C07D219/02C07D311/82C07D335/20C07D401/04C07D471/04C07D495/04G02B1/043

Abstract

Claims (25)

1 . A fused tricyclic compound of formula III:

wherein:

X is O;

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

R 1 and R 2 are independently at each occurrence H, an optional substituent, or —Y—P g , or two adjacent R 1 or R 2 groups, together with the atoms to which they are attached, combine to form a cycloalkyl or aryl ring optionally substituted with —Y-Pg g ;

EWG at each occurrence is cyano;

P g at each occurrence is independently a polymerizable group; and

Y at each occurrence is independently a linking group,

wherein the compound of formula I contains at least one Pg group.

2 . The compound of claim 1 wherein m, and n are independently 0 or 1.

3 . The compound of claim 1 wherein R 1 is H, 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 4 R 5 , benzyl, SO 3 H, or SO 3 Na, wherein R 4 and R 5 are independently H or C 1 -C 6 alkyl.

4 . The compound of claim 1 wherein R 2 is H, 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 4 R 5 , benzyl, SO 3 H, or SO 3 Na, wherein R 4 and R 5 are independently H or C 1 -C 6 alkyl.

5 . The compound of claim 1 wherein Pg at each occurrence independently comprises styryl, vinyl carbonate, vinyl ether, vinyl carbamate, N-vinyl lactam, N-vinylamide, (meth)acrylate, or (meth)acrylamide.

6 . The compound of claim 1 wherein Y at each occurrence is independently alkylene, cycloalkylene, heterocycloalkylene, arylene, heteroarylene, oxaalkylene, alkylene-amide-alkylene, alkylene-amine-alkylene, or combinations of any of the foregoing groups.

7 . The compound of claim 1 wherein the compound contains one Y—P g group.

8 . A compound according to claim 1 that is:

2-((9-(dicyanomethylene)-9H-xanthen-3-yl)oxy)ethyl methacrylate.

9 . An ophthalmic device that is a polymerization reaction product of a reactive mixture comprising: a monomer suitable for making the ophthalmic device; and (b) a compound according to claim 1 .

10 . The ophthalmic device of claim 9 wherein the monomer suitable for making the device is selected from a hydrophilic component, a hydrophobic component, a silicone-containing component, or a mixture of two or more thereof.

11 . The ophthalmic device of claim 9 that is a conventional (non-silicone) hydrogel or a silicone hydrogel.

12 . The ophthalmic device of claim 9 that is an intraocular lens or a soft contact lens.

13 . An ophthalmic device comprising a polymeric network and a non-reactive polymer comprising repeating units derived from a compound according to claim 1 .

14 . The ophthalmic device of claim 13 wherein the non-reactive polymer further comprises repeating units derived from an amide monomer, a monofunctional polyalkylene glycol, or a combination thereof.

15 . The ophthalmic device of claim 14 wherein the amide monomer is an acyclic amide of formula H1 or H2, a cyclic amide of formula H3, or combinations thereof:

wherein R 45 is H or methyl; V is a direct bond, —(CO)—, or —(CONHR 44 )—; R 44 is C 1 to C 3 alkyl; R 40 is H or C 1 to C 4 alkyl; R 41 is H, C 1 to C 4 alkyl, amino having up to two carbon atoms, amide having up to four carbon atoms, and alkoxy having up to two carbon groups; R 42 is H, C 1 to C 4 alkyl groups; or methoxy, ethoxy, hydroxyethyl, or hydroxymethyl; R 43 is H, C 1 to C 4 alkyl; or methoxy, ethoxy, hydroxyethyl, or hydroxymethyl; wherein the number of carbon atoms in R 40 and R 41 taken together is 8 or less; and wherein the number of carbon atoms in R 42 and R 43 taken together is 8 or less; and f is a number from 1 to 10.

Assignments (1)

Continuity (2)

References Cited (364)