# US 10,441,676 B2 · Light-adjustable hydrogel and bioanalogic intraocular lens

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- Number: US 10,441,676 B2
- Document ID: US10441676B2
- Status: Granted
- Kind: B2
- Application number: 15/190,715
- Filed: 2016-06-23
- Published: 2016-10-13
- Granted: 2019-10-15
- Earliest claimed: 2013-01-15
- Assignees: Medicem Institute s.r.o.
- Applicants: Medicem Ophthalmic (CY) Limited
- Inventors: Vladimir Stoy; Václav Petrák; Miroslav Dudi{hacek over (c)}
- Web page: https://patentgrep.com/patent/US10441676B2

## CPC

- A61L 27/16: obtained by reactions only involving carbon-to-carbon unsaturated bonds
- A61F 2/16: Intraocular lenses
- A61F 2/1613: {having special lens configurations, e.g. multipart lenses; having particular optical properties, e.g. pseudo-accommodative lenses, lenses having aberration corrections, diffractive lenses, lenses for variably absorbing electromagnetic radiation, lenses having variable focus}
- A61F 2/1627: {for changing index of refraction, e.g. by external means or by tilting}
- A61L 27/50: Materials characterised by their function or physical properties {, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials}
- A61L 27/52: Hydrogels or hydrocolloids
- C08F 220/20: of polyhydric alcohols or phenols {, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate}
- A61F 2002/1681: {having supporting structure for lens, e.g. haptics}
- A61F 2002/16965: {Lens includes ultraviolet absorber}
- A61L 2430/16: for reconstruction of eye parts, e.g. intraocular lens, cornea
- A61L: METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES (preservation of bodies or disinfecting characterised by the agents employed A01N; preserving, e.g. sterilising, food or foodstuffs A23; preparations for medical, dental or toiletry purposes A61K)
- A61F: FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS (dental prosthetics A61C)
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS

## Abstract

A bioanalogic implantable ophthalmic lens (“BIOL”) capable of replacing the natural crystalline lens (NCL) in its various essential functions after the NCL having been removed and BIOL implanted into the posterior eye chamber and placed into the capsular bag vacated from the NCL. At least the posterior surface of the lens has a convex shape and is made from a transparent flexible hydrogel material. At least the anterior and posterior optical surfaces are defined by rotation of one or more conic sections along the main optical axis and the surfaces defined by the rotation will include a plane perpendicular to the axis and conical surface symmetrical by the axis. A hydrogel implantable ophthalmic lens whose optical parameters can be optimized and/or customized by a controlled absorption of electromagnetic radiation resulting in a change of the refractive index of the irradiated hydrogel.

## Claims

### Claim 1

An in situ-adjustable crosslinked hydrogel ophthalmic implant comprising an acrylate or a methacrylate copolymer hydrogel wherein said copolymer comprises at least four co-monomers:
a) an acrylate ester or a methacrylate ester, each containing at least one pendant hydroxyl group;
b) a polyol acrylate ester, a polyol acrylate amide, a polyol methacrylate ester, or a polyol methacrylate amide, each with at least 2 acrylate or methacrylate groups per polyol ester or amide;
c) acrylic or methacrylic acid, or a derivative thereof, each having at least one pendant carboxyl group; and
d) a vinyl monomer, an acrylic monomer, or a methacrylic monomer, each having a pendant UV-absorbing group;
wherein refractive properties of said implant are adjustable by absorption of femtosecond laser pulses by said hydrogel resulting in a negative change of refractive index in selected locations of said implant.

### Claim 2 (depends on 1)

The hydrogel ophthalmic implant according to claim 1 wherein the implant has anterior and posterior refractive surfaces forming a lens with positive or negative refractive power.

### Claim 3 (depends on 2)

The hydrogel ophthalmic implant according to claim 2 wherein the lens is a posterior chamber lens for at least partial replacement of a natural crystalline lens.

### Claim 4 (depends on 2)

The hydrogel ophthalmic implant according to claim 2 wherein at least one of the refractive surfaces is an aspheric surface with negative spherical aberration.

### Claim 5 (depends on 2)

The hydrogel ophthalmic implant according to claim 2 wherein at least a major portion of the polymer of said hydrogel is a hydrophilic derivative of methacrylic acid.

### Claim 6 (depends on 5)

The hydrogel ophthalmic implant according to claim 5 wherein at least a major portion of the hydrophilic methacrylic acid derivative is a glycol ester of methacrylic acid.

### Claim 7 (depends on 2)

The hydrogel ophthalmic implant according to claim 2 wherein the covalently crosslinked hydrogel contains more than 30% by weight of liquid under equilibrium physiological conditions.

### Claim 8 (depends on 2)

The hydrogel ophthalmic implant according to claim 2 wherein the covalently crosslinked hydrogel contains less than 55% by weight of liquid under equilibrium physiological conditions.

### Claim 9 (depends on 2)

The hydrogel ophthalmic implant according to claim 2 wherein the covalently crosslinked hydrogel contains between 35% and 47.5% by weight of liquid under equilibrium physiological conditions.

### Claim 10 (depends on 2)

The hydrogel ophthalmic implant according to claim 2 wherein at least the posterior optical surface contributes refraction with negative spherical aberration.

### Claim 11 (depends on 2)

The hydrogel ophthalmic implant according to claim 2 wherein the posterior optical surface contributes refraction with negative spherical aberration between −0.1 microns and −2 microns.

### Claim 12 (depends on 11)

The hydrogel ophthalmic implant according to claim 11 wherein the negative spherical aberration is between −0.5 microns and −1.5 microns.

### Claim 13 (depends on 12)

The hydrogel ophthalmic implant according to claim 12 wherein the negative spherical aberration is between −0.75 microns and −1.25 microns on an aperture >4.5 mm.

### Claim 14 (depends on 1)

The hydrogel ophthalmic implant according to claim 1 wherein the monomer containing the pendant carboxyl group is a neutralized or a partially neutralized methacrylic acid.

### Claim 15 (depends on 1)

The hydrogel ophthalmic implant according to claim 1 wherein the monomer containing the pendant carboxyl group is present in a concentration between 0.1 molar % and 5 molar % based on all monomer units of the copolymer.

### Claim 16 (depends on 15)

The hydrogel ophthalmic implant according to claim 15 wherein the monomer containing the pendant carboxyl group is present in a concentration between 0.5 molar % and 2 molar % based on all monomer units of the copolymer.

### Claim 17 (depends on 1)

The hydrogel ophthalmic implant according to claim 1 wherein the monomer containing the pendant UV-absorbing group is present in a concentration between 0.1 molar % and 5 molar % based on all monomer units of the copolymer.

### Claim 18 (depends on 17)

The hydrogel ophthalmic implant according to claim 17 wherein the monomer containing the pendant UV-absorbing group is present in a concentration between 0.2 molar % and 2.5 molar % based on all monomer units of the copolymer.

### Claim 19 (depends on 1)

The hydrogel ophthalmic implant according to claim 1 wherein at least one of the UV-absorbing pendant groups is selected from the group consisting of derivatives of benzophenone, derivatives of benzotriazole, derivatives of coumarin and derivatives of fluorescein.

### Claim 20 (depends on 1)

The hydrogel ophthalmic implant according to claim 1 wherein the pendant carboxyl groups and the pendant UV-absorbing groups are present in a molar ratio between 0.25:1 and 5:1.

### Claim 21 (depends on 20)

The hydrogel ophthalmic implant according to claim 20 wherein the pendant carboxyl groups and the pendant UV-absorbing groups are present in a molar ratio between 0.5:1 and 3.5:1.

### Claim 22 (depends on 1)

The hydrogel ophthalmic implant according to claim 1 wherein the copolymer contains at least two different comonomers containing different UV-absorbing groups.

### Claim 23 (depends on 22)

The hydrogel ophthalmic implant according to claim 22 wherein at least one of the UV-absorbing groups is a benzophenone or a derivative thereof.

### Claim 24 (depends on 1)

The hydrogel ophthalmic implant according to claim 1, wherein the covalently crosslinked hydrogel contains 25% to 55% by weight of liquid under equilibrium physiological conditions.

### Claim 25 (depends on 1)

The hydrogel ophthalmic implant according to claim 1, wherein the covalently crosslinked hydrogel contains 25% to 30% by weight of liquid under equilibrium physiological conditions.
