Semifluorinated alkane compositions

Patent metadata

Field	Value
Publication number	US-9770508-B2
Application number	US-201314427969-A
Country	US
Kind code	B2
Filing date	Sep 12, 2013
Priority date	Sep 12, 2012
Publication date	Sep 26, 2017
Grant date	Sep 26, 2017

Abstract

The invention provides novel compositions comprising semifluorinated alkanes and at least one compound sensitive or prone to oxidation. The compositions can be used as medicines that are topically administered to an eye or ophthalmic tissue. The invention further provides kits comprising such compositions.

First claim

The invention claimed is:

1. A stable liquid composition comprising an active compound with more than one aliphatic double bond prone to oxidation, wherein the active compound is dissolved in a liquid vehicle comprising a semifluorinated alkane of formula
F(CF 2 ) n (CH 2 ) m H

wherein n and m are integers independently selected from the range of 3 to 20, and wherein the liquid vehicle is substantially free of water; and
wherein the active compound is an omega-3 or omega-6 fatty acid or derivative thereof, or a mixture of omega-3 or omega-6 fatty acids or derivatives thereof;
and wherein the composition comprises about 0.01-10 wt. % of the active compound.

2. The composition of claim 1 , wherein the active compound is a polyunsaturated fatty acid derivative which is an ester.

3. The composition of claim 1 , wherein the active compound is an omega-3 fatty acid selected from α-linolenic acid, docosahexaenoic acid, eicosapentaenoic acid, and ester derivatives thereof.

4. The composition of claim 3 , wherein the composition consists essentially of the one or more omega-3 fatty acids or ester derivatives thereof dissolved in the liquid semifluorinated alkane.

5. The composition of claim 4 , wherein the composition consists essentially of docosahexaenoic acid and/or eicosapentaenoic acid or alkyl ester derivatives thereof dissolved in a semifluorinated alkane of the formula F(CF 2 ) 6 (CH 2 ) 8 H.

6. The composition of claim 3 , wherein the semifluorinated alkane is selected from F(CF 2 ) 4 (CH 2 ) 5 H, F(CF 2 ) 4 (CH 2 ) 6 H, F(CF 2 ) 4 (CH 2 ) 8 H, F(CF 2 ) 6 (CH 2 ) 4 H, F(CF 2 ) 6 (CH 2 ) 6 H, F(CF 2 ) 6 (CH 2 ) 8 H, F(CF 2 ) 6 (CH 2 ) 10 H, F(CF 2 ) 8 (CH 2 ) 1014 and F(CF 2 ) 10 (CH 2 ) 12 H.

7. The composition of claim 6 , wherein the active compound is an omega-3 fatty acid or derivative thereof.

8. The composition of claim 7 , wherein the omega-3 fatty acid or derivative thereof is selected from one or more of docosahexaenoic acid, eicosapentaenoic acid, and alkyl ester derivatives thereof.

9. The composition of claim 8 , wherein the omega-3 fatty acid or derivative thereof is selected from docosahexaenoic acid ethyl ester or eicosapentaenoic acid ethyl ester.

10. The composition of claim 1 , wherein the semifluorinated alkane is selected from F(CF 2 ) 4 (CH 2 ) 5 H, F(CF 2 ) 4 (CH 2 ) 6 H, F(CF 2 ) 4 (CH 2 ) 8 H, F(CF 2 ) 6 (CH 2 ) 4 H, F(CF 2 ) 6 (CH 2 ) 6 H, F(CF 2 ) 6 (CH 2 ) 8 H, F(CF 2 ) 6 (CH 2 ) 10 H, F(CF 2 ) 8 (CH 2 ) 10 H and F(CF 2 ) 10 (CH 2 ) 12 H.

11. The composition of claim 1 , further comprising a lipid or oily excipient selected from triglyceride oils, mineral oil, medium chain triglycerides, oily fatty acids, isopropyl myristate, oily fatty alcohols, esters of sorbitol and fatty acids, oily sucrose esters, oily cholesterol esters, oily wax esters, glycerophospholipids, and sphingolipids.

12. The composition of claim 1 , further comprising an anti-inflammatory compound selected from the group of NSAIDs, corticosteroids and immunomodulators.

13. The composition of claim 1 , wherein the composition comprises an omega-3 fatty acid or derivative thereof, and wherein the omega-3 fatty acid or derivative thereof is the only active ingredient in the composition.

14. The composition of claim 1 , wherein the composition comprises an omega-3 fatty acid derivative selected from a derivative of eicosapentaenoic acid, a derivative of docosahexaenoic acid, a resolvin, and a neuroprotectin.

15. The composition of claim 1 , wherein the composition is microbiologically stable and does not comprise a preservative.

16. A method of treating a disease or condition of a patient in need of such treatment, comprising administering an effective amount of the composition of claim 1 to the patient, wherein the composition is topically administered to an eye or ophthalmic tissue, to the skin, or to the buccal, anal, vaginal, or nasal mucosa.

17. The method of claim 16 , wherein the disease or condition is a condition or disease of an eye or ophthalmic tissue.

18. The method of claim 17 , wherein the disease or condition is an inflammatory condition of the ophthalmic tissue or keratoconjunctivitis sicca (dry eye).

19. A method of stabilising an active compound with more than one aliphatic double bond prone to oxidation comprising the step of dissolving the active compound in a liquid vehicle comprising a semifluorinated alkane of formula
F(CF 2 ) n (CH 2 ) m H

wherein n and m are integers independently selected from the range of 3 to 20 and wherein the liquid vehicle is substantially free of water;
wherein the active compound is an omega-3 or omega-6 fatty acid or derivative thereof, or a mixture of omega-3 or omega-6 fatty acids or derivatives thereof;
and wherein the composition comprises about 0.01-10 wt. % of the active compound.

20. The method of claim 19 , wherein the semifluorinated alkane is selected from F(CF 2 ) 4 (CH 2 ) 5 H, F(CF 2 ) 4 (CH 2 ) 6 H, F(CF 2 ) 4 (CH 2 ) 8 H, F(CF 2 ) 6 (CH 2 ) 4 H, F(CF 2 ) 6 (CH 2 ) 6 H, F(CF 2 ) 6 (CH 2 ) 8 H, F(CF 2 ) 6 (CH 2 ) 10 H, F(CF 2 ) 8 (CH 2 ) 1014 and F(CF 2 ) 10 (CH 2 ) 12 H.

Assignees

• Novaliq Gmbh

Inventors

• Günther Bernhard
• Scherer Dieter
• Pettigrew Anthony

Classifications

• A61P37/06

  Immunosuppressants, e.g. drugs for graft rejection · CPC title

• A61P5/38

  of the suprarenal hormones · CPC title

• A61P37/02

  Immunomodulators · CPC title

• A61P43/00

  Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 · CPC title

• A61P27/04

  Artificial tears; Irrigation solutions · CPC title