Medical devices having homogeneous charge density and methods for making same

• US 9,612,364 B2
• Filed: 03/13/2015
• Issued: 04/04/2017
• Est. Priority Date: 05/04/2011
• Status: Active Grant

• Current Assignee: Johnson & Johnson Vision Care Incorporated (Johnson & Johnson)
• Original Assignee: Johnson & Johnson Vision Care Incorporated (Johnson & Johnson)
• 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.
• Primary Examiner(s): Yoon, Tae H
• Application Number:
  US14/657,217
• Publication Number:
  US 20150185365A1
• Time in Patent Office: 753 Days
• Field of Search: 523107, 528 25
• CPC Class Codes: A61K 31/4535 containing a heterocyclic ring having sulfur as a ring hetero atom, e.g. pizotifen
• CPC Class Codes: A61K 47/34 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 Class Codes: A61K 9/0051 Ocular inserts, ocular implants
• CPC Class Codes: C08L 101/14 the macromolecular compounds being water soluble or water swellable, e.g. aqueous gels
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: G02B 1/041 Lenses
• CPC Class Codes: G02B 1/043 Contact lenses

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.

Claims

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 μ

g and less than 200 μ

g.

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

g and about 100 μ

g.

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 μ

g/lens.

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

g/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.