Ophthalmic molding

• US 6,468,667 B1
• Filed: 06/30/2000
• Issued: 10/22/2002
• Est. Priority Date: 06/30/1999
• Status: Expired due to Fees

• Current Assignee: Novartis Ag
• Original Assignee: Novartis Ag
• Inventors: Lohmann, Dieter, Chabrecek, Peter, Streiff, Markus
• Primary Examiner(s): Barr, Michael
• Assistant Examiner(s): LIGHTFOOT, ELENA TSOY
• Application Number:
  US09/609,493
• Time in Patent Office: 844 Days
• Field of Search: 428/532, 427/2.24, 427/338, 427/337, 427/339, 623/6.62
• US Class Current: 428/532
• CPC Class Codes: A61L 27/34 Macromolecular materials
• CPC Class Codes: C08L 5/00 Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
• CPC Class Codes: G02B 1/043 Contact lenses
• CPC Class Codes: Y10T 428/31971 Of carbohydrate

Abstract

The invention relates to an ophthalmic molding such as a contact lens or any kind of ocular prostheses comprising an organic bulk material having covalently bonded to its surface an acceptor saccharide to which is enzymatically attached one or more further carbohydrates. The ophthalmic moldings of the invention have desirable characteristics regarding, for example, adherence to the substrate, durability, hydrophilicity, wettability or biocompatibility.

Claims

1. An ophthalmic molding comprising

(a) a bulk material carrying covalently linked photoinitiator molecules for radical polymerization on its surface;

and

(b) a surface coating obtained by co-graft polymerizing onto the bulk material surface;

(i) one or more different acceptor saccharides comprising an ethylenically unsaturated double bond; and

(ii) one or more hydrophilic macromonomers of formula

 

wherein R₄* is hydrogen or methyl, A₁ is —

O—

(CH₂)_2-4—

, —

O—

CH₂—

CH(OH)—

CH₂—

or a radical —

O—

(CH₂)_2-4—

NH—

C(O)—

, X is —

O—

or —

NH—

, (alk) is C₂-C₄-alkylene, Q is a monovalent group that is suitable to act as a polymerization chain-reaction terminator, p is an integer from 5 to 50,

R₃′

is hydrogen or methyl, and

 

is the 1,2-ethylene radical derived from acrylamide, N,N-dimethyl acrylamide or N-vinylpyrrolidone,

wherein, before or after said graft polymerization, a further carbohydrate selected from the group consisting of a galactose, mannose, fucose, galactosamine, N-acetylgalactosamine, N-acetylglucosamine, sialic acid and an oligosaccharide, is enzymatically attached to the acceptor saccharide.

3. An ophthalmic molding according to claim 1, wherein the acceptor saccharides comprising an ethylenically unsaturated double bond are of formula

wherein A is a radical of formula

4. An ophthalmic molding according to claim 3, wherein the radical (saccharide) is the radical of a mono-, di-, tri- or tetrasaccharide or a derivative thereof.

5. An ophthalmic molding according to claim 3, wherein the radical (saccharide) is selected from the group consisting of a lactose, lactobionic acid, N-acetyllactosamine and N-acetylgalactosamine.

6. An ophthalmic molding according to claim 1, wherein the enzymatically attached carbohydrate is sialic acid.

7. An ophthalmic molding according to claim 1, which is a contact lens or a corneal implant.

2. A process for the manufacture of an ophthalmic molding comprising the steps:

(a) providing an organic bulk material comprising covalently bound photoinitiator groups on its surface;

(b) co-graft polymerizing onto the bulk material surface;

(i) one or more different acceptor saccharides comprising an ethylenically unsaturated double bond, to which a further carbohydrate has been enzymatically attached, wherein the further carbohydrate is selected from the group consisting of a galactose, mannose, fucose, galactosamine, N-acetylgalactosamine, N-acetylglucosamine, sialic acid and an oligosaccharide; and

(ii) a hydrophilic macromonomer of formula

 

wherein R₄* is hydrogen or methyl, A₁ is —

O—

(CH₂)_2-4—

, —

O—

CH₂—

CH(OH)—

CH₂—

or a radical —

O—

(CH₂)_2-4—

NH—

C(O)—

, X is —

O—

or —

NH—

, (alk) is C₂-C₄-alkylene, Q is a monovalent group that is suitable to act as a polymerization chain-reaction terminator, p is an integer from 5 to 50, and

R₃′

is hydrogen or methyl, and

 

is the 1,2-ethylene radical derived from acrylamide, N,N-dimethyl acrylamide or N-vinylpyrrolidone.

8. A process for the manufacture of an ophthalmic molding comprising the steps:

(a) providing an organic bulk material comprising covalently bound photoinitiator groups on its surface;

(b) co-graft polymerizing onto the bulk material surface;

(i) one or more different acceptor saccharides comprising an ethylenically unsaturated double bond; and

(ii) a hydrophilic macromonomer of formula

 

wherein R₄* is hydrogen or methyl, A₁ is —

O—

(CH₂)_2-4—

, —

O—

CH₂—

CH(OH)—

CH₂—

or a radical —

O—

(CH₂)_2-4—

NH—

C(O)—

, X is —

O—

or —

NH—

, (alk) is C₂-C₄-alkylene, Q is a monovalent group that is suitable to act as a polymerization chain-reaction terminator, p is an integer from 5 to 50, and

R₃′

is hydrogen or methyl, and

 

is the 1,2-ethylene radical derived from acrylamide, N,N-dimethyl acrylamide or N-vinylpyrrolidone; and

(c) enzymatically attaching a further carbohydrate to the acceptor saccharide,

wherein the further carbohydrate is selected from the group consisting of a galactose, mannose, fucose, galactosamine, N-acetylgalactosamine, N-acetylglucosamine, sialic acid and an oligosaccharide.