Contact lens with optical prophylaxis
The present disclosure provides metalloporphyrin and metallochlorin compounds (e.g., compounds of Formula (II) and (III)), which are useful in the preparation of optical devices (e.g., contact lenses, intraocular lenses, implantable contact lenses) that protect retinal pigment epithelium by the selective blocking of blue light. Also provided are precursor porphyrin and chlorin compounds (e.g., compounds of Formula (I)), and compositions and optical devices incorporating the compounds of the disclosure. Also provided are methods of selecting appropriate metalloporphyrin and metallochlorin compounds for incorporation into optical devices wherein the devices mitigate damage to retinal epithelial cells while balancing changes to luminous transmission, discomfort glare, color distortion, and disruption of circadian rhythms.
1 . A compound of Formula (I):
or a salt, or tautomer thereof, wherein:
each R is independently hydrogen, halogen, substituted or unsubstituted C 1 -C 20 alkenyl, substituted or unsubstituted C 1 -C 20 alkynyl, or two adjacent R groups, together with the atoms to which they are attached, form a substituted or unsubstituted C 6 -C 14 aryl, substituted or unsubstituted C 5 -C 14 heteroaryl, or substituted or unsubstituted C 3 -C 14 heterocyclyl, or two adjacent R groups are each substituted or unsubstituted C 1 -C 20 alkyl and, together with the atoms to which they are attached, form a substituted or unsubstituted C 3 -C 14 carbocyclyl;
each R 1 is independently hydrogen, halogen, substituted or unsubstituted C 1 -C 20 alkyl, substituted or unsubstituted C 1 -C 20 alkenyl, substituted or unsubstituted C 1 -C 20 alkynyl, or two adjacent R 1 groups, together with the atoms to which they are attached, form a substituted or unsubstituted C 6 -C 14 aryl, substituted or unsubstituted C 3 -C 14 carbocyclyl, substituted or unsubstituted C 5 -C 14 heteroaryl, or substituted or unsubstituted C 3 -C 14 heterocyclyl; or one instance of R 1 and R on the same carbon form with that carbon a carbonyl;
A 1 , A 2 , and A 3 are independently hydrogen or a substituted aryl of formula:
each R 2 is independently hydrogen, halogen, —NO 2 , substituted or unsubstituted alkyl, —NHR A , —N(R A ) 2 , or —OR B ;
is a single or double bond, provided that when is double bond, then each R 1 is absent;
each L is independently:
wherein:
n is 1-6;
each occurrence of R A is independently substituted or unsubstituted C 1 -C 20 alkyl; and
y labels the site with attachment to group X;
each X is independently hydrogen, halogen, substituted or unsubstituted C 1 -C 20 alkyl, or a polymerizable group, provided that at least one X is a polymerizable group; and
each occurrence of R B is independently hydrogen, substituted or unsubstituted acyl, substituted or unsubstituted C 1 -C 20 alkyl, substituted or unsubstituted C 1 -C 20 alkenyl, substituted or unsubstituted C 1 -C 20 alkynyl, substituted or unsubstituted C 3 -C 14 carbocyclyl, substituted or unsubstituted C 3 -C 14 heterocyclyl, substituted or unsubstituted C 6 -14 aryl, or substituted or unsubstituted C 5 -14 heteroaryl.
2 . The compound of claim 1 , or a salt, or tautomer thereof, wherein each R is independently hydrogen, halogen, or two adjacent R groups, together with the atoms to which they are attached, form a substituted or unsubstituted C 3 -C 14 carbocyclyl.
3 . The compound of claim 1 , or a salt, or tautomer thereof, wherein each R 2 is independently hydrogen, —OR B , or halogen.
4 . The compound of claim 1 , or a salt, or tautomer thereof, wherein each X is independently an acrylate, a methacrylate, an acrylamide, a methacrylamide, a styrene, a vinyl sulfone, or alkenyl; wherein each X is substituted or unsubstituted.
5 . The compound of claim 1 , or a salt, or tautomer thereof, wherein each X is independently
6 . The compound of claim 1 , wherein the compound is of Formula (I-a), (I-b), (I-b-1), (I-b-2), (I-b-3), (I-b-4), (I-b-5), (I-b-6), or (I-c):
or a salt, or tautomer thereof.
7 . The compound of claim 1 , wherein the compound is
or a salt or tautomer thereof.