Biomedical devices
View Patent ↗The present invention is concerned with biomedical device comprising (a) a biocompatible organic or inorganic bulk material and (b) a coating comprising polymerizable carbon-carbon double bonds covalently attached to at least part of the bulk surface. The biomedical devices of the invention are radiation sensitive and may be used, for example, as ready-to-use corneal onlay in ophthalmic surgery.
1. A biomedical device comprising
(a) a biocompatible organic bulk material, wherein the biocompatible organic bulk material is selected from the group consisting of a polysiloxane, perfluoroalkyl polyether, fluorinated poly(meth)acrylate, polyalkyl (meth)acrylate, a fluorinated polyolefin; and
(b) a coating covalently attached to at least part of the bulk surface, wherein said coating comprises polymerizable carbon-carbon double bonds, and wherein the coating is obtained by covalently coupling functional groups of the surface of the medical device with a multifunctional compound comprising at least one polymerizable carbon-carbon double bond and at least one additional functional group that is coreactive to the functional groups of the device surface.
2. The biomedical device according to claim 1 , which is an ophthalmic device.
3. The ophthalmic device according to claim 2 , which is a contact lens, intraocular lens, corneal onlay, corneal implant, or an artificial cornea.
4. A biomedical device comprising
(a) a biocompatible organic bulk material, wherein the biocompatible organic bulk material is selected from the group consisting of a polysiloxane, perfluoroalkyl polyether, fluorinated poly(meth)acrylate, polyalkyl (meth)acrylate, a fluorinated polyolefin; and
(b) a coating covalently attached to at least part of the bulk surface, wherein said coating comprises polymerizable carbon-carbon double bonds, wherein the coating is obtained by covalently coupling functional groups of the surface of the medical device with a natural or synthetic polymer comprising co-reactive groups, and covalently coupling a multifunctional compound comprising at least one polymerizable carbon-carbon double bond and at least one additional functional group to said natural or synthetic polymer.
5. The biomedical device according to claim 1 , wherein the multifunctional compound is selected from the group consisting of a compound of formula
wherein
R 1 is hydrogen, C 1 –C 4 -alkyl or halogen;
R 2 is hydrogen, unsubstituted or hydroxy-substituted C 1 –C 6 -alkyl or phenyl;
R 3 and R 3 ′ are each an ethylenically unsaturated radical having from 2 to 6 C-atoms, or R 3 and R 3 ′ together form a bivalent radical—C(R 4 )═C(R 4 ′)— wherein R 4 and R 4 ′ are each independently hydrogen, C 1 –C 4 -alkyl or halogen and
(Alk*) is C 1 –C 6 -alkylene, and (Alk**) is C 2 –C 12 -alkylene;
R 5 is a bivalent organic radical, which may be substituted;
R 6 is hydrogen, methyl or phenyl;
s and t independently of each other is an integer 0 or 1;
X 1 and X 2 are each independently from the other, O, NH, or N—C 1 –C 4 -alkyl; and
R 7 is a carboxy derivative.
6. The biomedical device according to claim 4 , wherein the multifunctional compound is selected from the group consisting of a compound of formula
R 1 is hydrogen, C 1 –C 4 -alkyl or halogen;
R 2 is hydrogen, unsubstituted or hydroxy-substituted C 1 –C 6 -alkyl or phenyl;
R 3 and R 3 ′ are each an ethylenically unsaturated radical having from 2 to 6 C-atoms, or R 3 and R 3 ′ together form a bivalent radical—C(R 4 )═C(R 4 ′)— wherein R 4 and R 4 ′ are each independently hydrogen, C 1 –C 4 -alkyl or halogen and
(Alk*) is C 1 –C 6 -alkylene, and (Alk**) is C 2 –C 12 -alkylene;
R 5 is a bivalent organic radical, which may be substituted;
R 6 is hydrogen, methyl or phenyl;
s and t independently of each other is an integer 0 or 1;
X 1 and X 2 are each independently from the other, O, NH, or N—C 1 –C 4 -alkyl; and
R 7 is a carboxy derivative.
7. The biomedical device according to claim 6 , wherein the natural or synthetic polymer is a glycoprotein.
8. The biomedical device according to claim 7 , wherein the glycoprotein is a collagen.
9. The biomedical device according to claim 8 , wherein the multifunctional compound is a compound of formula (1a) or (1b).
10. The biomedical device according to claim 9 , which is an ophthalmic device.
11. The opththalmic device according to claim 10 , which is a contact lens, an intraocular lens or an artificial cornea.
12. A process for obtaining a biomedical device according to claim 1 by coating a biomedical device the process comprising the steps of
(a) providing a biomedical device comprising functional groups on its surface, and
(b) covalently attaching a multifunctional compound comprising at least one polymerizable carbon-carbon double bond and at least one additional functional group that is coreactive to the functional groups of the surface of the biomedical device.
13. A process for obtaining a biomedical device according to claim 6 by coating a biomedical device the process comprising the steps of
(a) providing a biomedical device comprising functional groups on its surface, and
(b) covalently coupling functional groups of the surface of the medical device with a natural or synthetic polymer comprising co-reactive groups, and
(c) covalently coupling a multifunctional compound comprising at least one polymerizable carbon-carbon double bond and at least one additional functional group that is coreactive to the reactive groups of said natural or synthetic polymer.
14. The process for the coating of a biomedical device according to claim 12 , wherein the multifunctional compound is selected from the group consisting of a compound of formula
wherein
R 1 is hydrogen, C 1 –C 4 -alkyl or halogen;
R 2 is hydrogen, unsubstituted or hydroxy-substituted C 1 –C 6 -alkyl or phenyl;
R 3 and R 3 ′ are each an ethylenically unsaturated radical having from 2 to 6 C-atoms, or R 3 and R 3 ′ together form a bivalent radical—C(R 4 )═C(R 4 ′)— wherein R 4 and R 4 ′are each independently hydrogen, C 1 –C 4 -alkyl or halogen and
(Alk*) is C 1 –C 6 -alkylene, and (Alk**) is C 2 –C 12 -alkylene;
R 5 is a bivalent organic radical, which may be substituted;
R 6 is hydrogen, methyl or phenyl;
s and t independently of each other is an integer 0 or 1;
X 1 and X 2 are each independently from the other, O, NH, or N—C 1 –C 4 -alkyl; and
R 7 is a carboxy derivative.
15. The process for the coating of a biomedical device according to claim 13 , wherein the multifunctional compound is selected from the group consisting of a compound of formula
wherein
R 1 is hydrogen, C 1 –C 4 -alkyl or halogen;
R 2 is hydrogen, unsubstituted or hydroxy-substituted C 1 –C 6 -alkyl or phenyl;
R 3 and R 3 ′ are each an ethylenically unsaturated radical having from 2 to 6 C-atoms, or R 3 and R 3 ′ together form a bivalent radical—C(R 4 )═C(R 4 ′)— wherein R 4 and R 4 ′ are each independently hydrogen, C 1 –C 4 -alkyl or halogen and
(Alk*) is C 1 –C 6 -alkylene, and (Alk**) is C 2 –C 12 -alkylene;
R 5 is a bivalent organic radical, which may be substituted;
R 6 is hydrogen, methyl or phenyl;
s and t independently of each other is an integer 0 or 1;
X 1 and X 2 are each independently from the other, O, NH, or N—C 1 –C 4 -alkyl; and
R 7 is a carboxy derivative.
16. The process for the coating of a biomedical device according to claim 14 , wherein the multifunctional compound is of formula (1a) or (1b).
17. The process for the coating of a biomedical device according to claim 15 , wherein the multifunctional compound is of formula (1a) or (1b).
18. The method of using a medical device according to claim 1 as an intraocular lens, which comprises implanting the device into or onto the cornea.
19. The biomedical device according to claim 4 , which is an ophthalmic device.