Ionic silicone hydrogels comprising pharmaceutical and/or neuticeutical components and having improved hydrolytic stability

• US 9,101,667 B2
• Filed: 07/18/2014
• Issued: 08/11/2015
• Est. Priority Date: 09/30/2008
• Status: Active Grant

• Current Assignee: Johnson & Johnson Vision Care Incorporated (Johnson & Johnson)
• Original Assignee: Johnson & Johnson Vision Care Incorporated (Johnson & Johnson)
• Inventors: Raja, Ranganath, Muthukrishnan, Sharmila, Surendran, C., Mahadevan, Shivkumar, Maggio, Thomas L., Alli, Azaam, Joslin, Scott L., Sridharan, R.
• Primary Examiner(s): ZIMMER, MARC S
• Application Number:
  US14/335,111
• Publication Number:
  US 20140329859A1
• Time in Patent Office: 389 Days
• Field of Search: None
• US Class Current: 1/1
• 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: C08F 220/04 Acids; Metal salts or ammonium salts thereof
• CPC Class Codes: C08F 220/06 Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
• CPC Class Codes: C08F 220/20 of polyhydric alcohols or phenols , e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
• CPC Class Codes: C08F 220/54 Amides , e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
• CPC Class Codes: C08F 230/08 containing silicon
• CPC Class Codes: C08F 290/068 Polysiloxanes
• CPC Class Codes: C08L 51/085 on to polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

The present invention relates to ionic silicone hydrogel polymers displaying improved thermal stability. More specifically, the present invention relates to a polymer formed from reactive components comprising at least one silicone component and at least one ionic component comprising at least one anionic group. The polymers of the present invention display good thermal stability and desirable protein uptake.

Claims

1. A contact lens formed from reactive components comprising about 0.1 to about 10 mmol/100 gm reactive mixture of at least one anionic component comprising at least one carboxylic acid group and at least one silicone component selected from the group consisting of reactive polydialkylsiloxane selected from compounds of Formula I:

2. The contact lens of claim 1 wherein said reactive components are free of TRIS.

3. The contact lens of claim 2 wherein said ionic component comprises at least one polymerizable group and three to ten carbon atoms.

4. The contact lens of claim 2 where said ionic component comprises three to eight carbon atoms.

5. The contact lens of claim 1 wherein said ionic component is a carboxylic acid containing component selected from the group consisting of free radical reactive carboxylic acids comprising 1-8 carbon atoms.

6. The contact lens of claim 1 wherein said ionic component comprises at least one carboxylic acid group.

7. The contact lens of claim 1 wherein said carboxylic acid-containing component is selected from the group consisting of (meth)acrylic acid, acrylic acid, itaconic acid, crotonic acid, cinnamic acid, vinylbenzoic acid, fumaric acid, maleic acid, N-vinyloxycarbonyl alanine, 3-acrylamidopropionic acid, 4-acrylamidobutanoic acid, 5-acrylamidopentanoic acid, N-vinyloxycarbonyl-α

-alanine, N-vinyloxycarbonyl-β

-alanine (VINAL), 2-vinyl-4,4-dimethyl-2-oxazolin-5-one (VDMO), reactive sulphonate salts, including sodium-2-(acrylamido)-2-methylpropane sulphonate, 3-sulphopropyl (meth)acrylate potassium salt, 3-sulphopropyl (meth)acrylate sodium salt, bis 3-sulphopropyl itaconate di sodium, bis 3-sulphopropyl itaconate di potassium, vinyl sulphonate sodium salt, vinyl sulphonate salt, styrene sulphonate, 2-sulphoethyl methacrylate and mixtures thereof.

8. The contact lens of claim 1 wherein said carboxylic acid-containing component comprises methacrylic acid, 3-acrylamidopropionic acid, 4-acrylamidobutanoic acid, 5-acrylamidopentanoic acid, N-vinyloxycarbonyl-α

-alanine, N-vinyloxycarbonyl-β

-alanine (VINAL), and mixtures thereof.

9. The contact lens of claim 8 wherein said carboxylic acid-containing component comprises methacrylic acid.

10. The contact lens of claim 1 wherein said at least one silicone component is selected from the group consisting of mono(meth)acryloxypropyl terminated mono-n-C_1-4alkyl terminated polydialkylsiloxane, (meth)acryloxypropyl-terminated polydialkylsiloxane, mono-(3-methacryloxy-2-hydroxypropyloxy)propyl terminated, mono-C_1-4alkyl alkyl terminated polydialkylsiloxane and combinations thereof.

11. The contact lens of claim 1 wherein said at least one silicone component is selected from mono(meth)acryloxypropyl terminated mono-n-butyl terminated polydimethylsiloxane, mono(meth)acryloxypropyl terminated polydimethylsiloxane, mono-(3-methacryloxy-2-hydroxypropyloxy)propyl terminated, mono-butyl terminated polydialkylsiloxane mono-(3-methacryloxy-2-hydroxypropyloxy)propyl terminated, mono-methyl terminated polydialkylsiloxane combinations thereof and the like.

12. The contact lens of claim 1 wherein said at least one silicone component is selected from monomethacryloxypropyl-terminated mono-n-butyl terminated polydimethysiloxane, methacryloxypropyl-terminated polydimethylsiloxane and mono-(3-methacryloxy-2-hydroxypropyloxy)propyl terminated, mono-butyl terminated polydimethylsiloxane and mixtures thereof.

13. The contact lens of claim 1 wherein said at least one pharmaceutical or neutraceutical component is cationic.

14. The contact lens 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 and the like.

15. The contact lens 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 and the like.

16. The contact lens of claim 1 wherein said at least one pharmaceutical or neutraceutical 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 and the like.

17. The contact lens of claim 1, 14, 15 or 16, wherein said at least one pharmaceutical or neutraceutical component is added in a symptom mitigating effective amount.

18. The contact lens of claims 17 wherein said symptom mitigating effective amount is between about 5 μ

g and about less than 200 μ

g.

19. The contact lens of claims 17 wherein said symptom mitigating effective amount is between about 9 μ

g and about 100 μ

g.

20. The contact lens of claims 17 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.

21. The contact lens of claim 1 wherein said contact lens absorbs at least about 50 μ

g lysozyme.

22. The contact lens of claim 1 wherein said contact lens absorbs at least about 100 μ

g lysozyme.

23. The contact lens of claim 1 wherein said contact lens absorbs at least about 200 μ

g lysozyme.

24. The contact lens of claim 1 wherein said contact lens absorbs about 3 μ

g or less lipocalin.

25. The contact lens of claim 1 wherein at least about 60% of all proteins absorbed in or on said contact lens are in native form.

26. The contact lens of claim 1 wherein at least about 75% of all proteins absorbed in or on said contact lens are in native form.

27. The contact lens of claim 1 further comprising a water content of at least about 15%.

28. The contact lens of claim 1 further comprising a Dk of at least about 50.

29. The contact lens of claim 28 wherein at least about 75% of all proteins absorbed in or on said contact lens are in native form.