Medical devices having homogeneous charge density and methods for making same

Patent metadata

Field	Value
Publication number	US-9612364-B2
Application number	US-201514657217-A
Country	US
Kind code	B2
Filing date	Mar 13, 2015
Priority date	May 4, 2011
Publication date	Apr 4, 2017
Grant date	Apr 4, 2017

Abstract

The present invention relates to ionic silicone hydrogel polymers comprising at least one pharmaceutical or nutriceutical component and displaying improved lysozyme uptake, low contact angle and reduced water soluble polymeric ammonium salt uptake.

First claim

We claim:

1. A silicone hydrogel formed from a reactive mixture comprising
major polymerizable components comprising at least one reactive silicone-containing component, at least one reactive ionic monomer, crosslinker, and optional reactive hydrophilic components; and
minor components that are optionally polymerizable comprising at least one pharmaceutical compound or nutriceutical compound, and optional additional minor polymerizable components selected from the group consisting of visibility tint and dyes, UV absorbers, photochromic compounds, and mixtures thereof;
wherein said major polymerizable components comprise a single reactive functionality; and wherein any polymerizable components in the reaction mixture which have a reactive functionality different than said single reactive functionality are present in a concentration less than 0.5 mol %.

2. The silicone hydrogel of claim 1 wherein said single reactive functionality is selected from the group consisting of acrylate, methacrylate, acrylamide, methacrylamide, vinyl and styryl.

3. The silicone hydrogel of claim 1 wherein said single reactive functionality is selected from the group consisting of acrylamide, methacrylamide and vinyl.

4. The silicone hydrogel of claim 1 wherein said single reactive functionality is methacrylamide and said reactive ionic monomer comprises at least one acrylamido sulphonic acid or acrylamido sulphonic acid salt.

5. The silicone hydrogel of claim 4 wherein said acrylamido sulphonic acid comprises an alkylene group comprising 2 to 4 carbon atoms.

6. The silicone hydrogel of claim 4 wherein said acrylamido sulphonic acid salt comprises 2-acrylamido-2-methylpropane sulfonic acid salt.

7. The silicone hydrogel of claim 1 wherein said at least one pharmaceutical or nutraceutical component is cationic.

8. The silicone hydrogel of claim 1 wherein said at least one pharmaceutical or neutraceutical component is selected from the group consisting of
atropine, pirenzepine, doxycycline, brimonidine, brinzolamide, dorzolamide, betaxolol, apraclonidine, ccr2 antagonist, olopatadine, alcaftadine, betaxolol, bupivacaine, carbachol, carteolol, chlortetracycline, cyclopentolate, dibutoline, dipivefrin, ephedrine, erythromycin, gentamycin, gramicidin, homatropine ketotifen, levobunolol, levocabastine, lidocaine, lignocaine, lomefloxacin, mepivacaine, naphazoline, neomycin, ofloxacin, oxybuprocaine, pheniramine, physostigmine, pilocarpine, polymyxin B, proparacaine, pyrilamine, tetracaine, tetracycline, tetrahydozoline, timolol, tropicamide, vidarabine, pharmaceutically acceptable salts thereof and combinations thereof.

9. The silicone hydrogel of claim 1 wherein said at least one pharmaceutical or neutraceutical component is selected from the group consisting of atropine, pirenzepine, doxycycline, brimonidine, brinzolamide, dorzolamide, betaxolol, apraclonidine, ccr2 antagonist, olopatadine, alcaftadine, betaxolol, bupivacaine, carbachol, carteolol, chlortetracycline, cyclopentolate, dibutoline, dipivefrin, erythromycin, gentamycin, gramicidin, homatropine ketotifen, levobunolol, levocabastine, lidocaine, lignocaine, lomefloxacin, mepivacaine, naphazoline, ofloxacin, pheniramine, physostigmine, pilocarpine, polymyxin B, proparacaine, pyrilamine, tetracaine, tetrahydozoline, timolol, tropicamide, pharmaceutically acceptable salts thereof and combinations thereof.

10. The silicone hydrogel of claim 1 wherein said at least one pharmaceutical or nutraceutical component is selected from the group consisting of atropine, ketotifen, olopatadine, alcaftadine, levocabastine, pirenzepine, doxycycline, brimonidine, brinzolamide, dorzolamide, betaxolol, apraclonidine, ccr2 antagonist, olopatadine, pharmaceutically acceptable salts thereof and combinations thereof.

11. A contact lens comprising the silicone hydrogel of claim 1 , wherein said at least one pharmaceutical or nutraceutical component in a symptom mitigating effective amount.

12. The contact lens of claim 11 wherein said symptom mitigating effective amount is between about 5 μg and less than 200 μg.

13. The contact lens of claim 11 wherein said symptom mitigating effective amount is between about 9 μg and about 100 μg.

14. The contact lens of claim 11 wherein said symptom mitigating effective amount alleviates symptoms for between about 5 minutes, and about 12 hours from insertion of said contact lens on a human's eye.

15. The contact lens of claim 11 wherein said contact lens comprises a modulus which increases less than 30% after three autoclave cycles.

16. The contact lens of claim 11 further comprising a lysozyme uptake of at least 70 μg/lens.

17. The contact lens of claim 11 further comprising a lysozyme uptake of at least 100 μg/lens.

18. The contact lens of claim 11 further comprising a water content of between about 20% and about 70%.

19. The contact lens of claim 11 further comprising a water content of between about 25% and about 65%.

20. The silicone hydrogel of claim 1 wherein said single reactive functionality is selected from (meth)acrylamides.

21. The silicone hydrogel of claim 1 wherein said single reactive functionality is selected from (meth)acrylates.

22. The silicone hydrogel of claim 1 wherein said single reactive functionality is selected from vinyls.

23. The silicone hydrogel of claim 20 wherein said reactive ionic monomer is selected from the group consisting of 3-acrylamidopropionic acid, 4-acrylamidobutanoic acid, 5-acrylamidopentanoic acid, sodium-2-(acrylamido)-2-methylpropane sulphonate, 2-acrylamido-2-methylpropane sulfonic acid and combinations thereof.

24. The silicone hydrogel of claim 21 wherein said reactive ionic monomer is selected from the group consisting of (meth)acrylic acid, acrylic acid, 3-sulphopropyl (meth)acrylate potassium salt, 3-sulphopropyl (meth)acrylate sodium salt, sulphoethyl methacrylate, and mixtures thereof.

25. The silicone hydrogel of claim 21 wherein said reactive ionic monomer comprises (meth)acrylic acid.

26. The silicone hydrogel of claim 22 wherein said reactive ionic monomer is selected from the group consisting of N-vinyloxycarbonyl-α-alanine, N-vinyloxycarbonyl-β-alanine, 2-vinyl-4,4-dimethyl-2-oxazolin-5-one, vinyl sulphonate sodium salt, vinyl sulphonate salt, and mixtures thereof.

Assignees

• Johnson & Johnson Vision Care

Inventors

• Mahadevan Shivkumar
• Fadli Zohra
• Scales Charles
• Maggio Thomas
• Venkatasubban Kunisi
• George Eric R
• Ford James D
• Davis Carrie L
• Hansen Leah
• Joslin Scott L
• Vanderlaan Douglas G
• Raja Ranganath
• Muthukrishnan Sharmila
• Surendran C
• Sridharan R

Classifications

• G02B1/043 Primary

  Contact lenses · CPC title

• A61K9/0051

  Ocular inserts or implants · CPC title

• A61K47/34

  Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers (A61K47/10 takes precedence) · CPC title

• A61K31/4535

  containing a heterocyclic ring having sulfur as a ring hetero atom, e.g. pizotifen · CPC title

• G02B1/041

  Lenses · CPC title