Polymerizable fused tricyclic compounds as absorbers of uv and visible light
AssigneeJohnson & Johnson Vision Care, Inc.
InventorsShivkumar Mahadevan, Dawn D. Wright
Life of this patent
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Abstract
Described are polymerizable fused tricyclic compounds of formula I: wherein R1, R2, R3, m, n, t, and rings B, C, and D are as defined herein. The compounds absorb various wavelengths of ultraviolet and/or visible light (such as high energy visible light) and are suitable for incorporation in a variety of products, such as biomedical devices and ophthalmic devices.
Claims26
1-18. (canceled)
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 fused tricyclic compound of formula I:
- wherein:
- m, n, and t are independently 0, 1, 2, 3, or 4;
- R1 R2, and R3 are independently at each occurrence H, an optional substituent, or —Y—Pg, or two adjacent R1, R2, or R3 groups, together with the atoms to which they are attached, combine to form a cycloalkyl or aryl ring optionally substituted with —Y—Pg;
- B represents a 5, 6, or 7 membered ring which is aromatic, saturated, or partially unsaturated optionally having up to three heteroatoms independently selected from O, S, N, and NR6, wherein R6 is H, C1-C6 alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, or Y—Pg;
- one of C and D represents a 5, 6, or 7 membered ring which is aromatic, saturated, or partially unsaturated optionally having up to three heteroatoms independently selected from O, S, N, and NR6, and the other of C and D is a 6 membered saturated or partially unsaturated heterocycloalkyl ring having at least one ring carbon atom and at least one heterogroup independently selected from O, S, NR6, SO, or SO2, the heterocycloalkyl ring being substituted at one ring carbon atom with a group of formula ═C(EWG)(R7), wherein R7 is EWG or —C(═O)-T-Y—Pg, and EWG at each occurrence is independently an electron withdrawing group;
- Pg at each occurrence is independently a polymerizable group;
- Y at each occurrence is independently a linking group;
- and
- T at each occurrence is independently a bond, O, or NR6,
- wherein the compound of formula I contains at least one Po group.
An ophthalmic device comprising a polymeric network and a non-reactive polymer comprising repeating units derived from a fused tricyclic compound of formula I:
- wherein:
- m, n, and t are independently 0, 1, 2, 3, or 4;
- R1 R2, and R3 are independently at each occurrence H, an optional substituent, or —Y—Pg, or two adjacent R1, R2, or R3 groups, together with the atoms to which they are attached, combine to form a cycloalkyl or aryl ring optionally substituted with —Y—Pg;
- B represents a 5, 6, or 7 membered ring which is aromatic, saturated, or partially unsaturated optionally having up to three heteroatoms independently selected from O, S, N, and NR6, wherein R6 is H, C1-C6 alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, or Y—Pg;
- one of C and D represents a 5, 6, or 7 membered ring which is aromatic, saturated, or partially unsaturated optionally having up to three heteroatoms independently selected from O, S, N, and NR6, and the other of C and D is a 6 membered saturated or partially unsaturated heterocycloalkyl ring having at least one ring carbon atom and at least one heterogroup independently selected from O, S, NR6, SO, or SO2, the heterocycloalkyl ring being substituted at one ring carbon atom with a group of formula ═C(EWG)(R7), wherein R7 is EWG or —C(═O)-T-Y—Po, and EWG at each occurrence is independently an electron withdrawing group;
- Pg at each occurrence is independently a polymerizable group;
- Y at each occurrence is independently a linking group;
- and
- T at each occurrence is independently a bond, O, or NR6,
- wherein the compound of formula I contains at least one Pg group.
27-28. (canceled)
Dependencies are inferred from the claim text.