Topical pharmaceutical composition based on semifluorinated alkanes

• US 10,130,707 B2
• Filed: 05/24/2012
• Issued: 11/20/2018
• Est. Priority Date: 05/25/2011
• Status: Active Grant

• Current Assignee: Dermaliq Therapeutics Incorporated
• Original Assignee: Novaliq GmbH
• Inventors: Gunther, Bernhard, Theisinger, Bastian, Theisinger, Sonja, Scherer, Dieter
• Primary Examiner(s): Soroush, Layla
• Application Number:
  US14/122,044
• Publication Number:
  US 20140100180A1
• Time in Patent Office: 2,371 Days
• Field of Search: 514217
• CPC Class Codes: A61K 31/355 Tocopherols, e.g. vitamin E
• CPC Class Codes: A61K 31/436 the heterocyclic ring system containing a six-membered ring having oxygen as a ring hetero atom, e.g. rapamycin
• CPC Class Codes: A61K 45/06 Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
• CPC Class Codes: A61K 47/06 Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
• CPC Class Codes: A61K 9/0014 Skin, i.e. galenical aspects of topical compositions non-active ingredients are additionally classified in A61K47/00; A61K9/0009, A61K9/0021, A61K9/7015, A61K9/7023 take precedence; cosmetic preparations A61K8/00, A61Q; preparations for wound dressings or bandages A61L26/00
• CPC Class Codes: A61K 9/08 Solutions composition of solutions A61K47/00
• CPC Class Codes: A61K 9/1075 Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers A61K9/0026 takes precedence
• CPC Class Codes: A61P 17/00 Drugs for dermatological disorders
• CPC Class Codes: A61P 17/02 for treating wounds, ulcers, burns, scars, keloids, or the like
• CPC Class Codes: A61P 17/04 Antipruritics
• CPC Class Codes: A61P 17/06 Antipsoriatics
• CPC Class Codes: A61P 17/10 Anti-acne agents
• CPC Class Codes: A61P 17/12 Keratolytics, e.g. wart or anti-corn preparations
• CPC Class Codes: A61P 17/14 for baldness or alopecia
• CPC Class Codes: A61P 29/00 Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
• CPC Class Codes: A61P 31/04 Antibacterial agents
• CPC Class Codes: A61P 31/10 Antimycotics
• CPC Class Codes: A61P 31/12 Antivirals
• CPC Class Codes: A61P 37/06 Immunosuppressants, e.g. drugs for graft rejection
• CPC Class Codes: A61P 37/08 Antiallergic agents antiasthmatic agents A61P11/06; ophthalmic antiallergics A61P27/14

Abstract

The invention provides liquid or semi-solid pharmaceutical compositions for topical administration comprising a semifluorinated alkane. The compositions are useful for the delivery of active ingredients into the deep layers of the skin or skin appendages. Various active ingredients may be incorporated, such as immunosuppressants, antiinfectives, antifungal agents, antiinflammatory agents, and retinoids.

Claims

1. A method for the prevention or treatment of a disease or condition affecting the skin, wherein the disease or condition affecting the skin is psoriasis, comprising administering to the skin a topical pharmaceutical composition comprising an effective amount of an active ingredient which is an immunosuppressant selected from tacrolimus, sirolimus, and ciclosporin A, and a semifluorinated alkane according to formula

RFRH

wherein RF is a linear perfluorinated hydrocarbon segment with 4 to 12 carbon atoms, and RH is a linear alkyl group with 4 to 8 carbon atoms;

wherein the semifluorinated alkane is selected from F4H5 and F6H8, wherein F means a perfluorinated hydrocarbon segment, H means a non-fluorinated segment, and the number is the number of carbon atoms of the respective segment;

and wherein the composition is in the form of a liquid solution; and

wherein the composition comprises a physiologically acceptable cosolvent selected from ethanol, isopropyl alcohol, glycerol, and propylene glycol.

2. The method of claim 1, wherein the semifluorinated alkane is F6H8.

3. The method of claim 1, wherein the composition is in the form of a single-phase liquid solution.

4. The method of claim 1, wherein the semifluorinated alkane is F4H5.

5. The method of claim 1, wherein the disease or condition affects the vital epidermis, dermis, and/or hypodermis of the skin.

6. The method of claim 1, wherein the active ingredient is delivered to the vital layers below the stratum corneum of the epidermis.

7. The method of claim 1, wherein the method is for the prevention or treatment of skin affected by psoriasis, and wherein the topical pharmaceutical composition is administered to the skin.

8. The method of claim 1, wherein the immunosuppressant is tacrolimus.

9. The method of claim 4, wherein the physiologically acceptable cosolvent is selected from ethanol and isopropyl alcohol.

10. The method of claim 2, wherein the immunosuppressant is tacrolimus.

11. The method of claim 1, wherein the physiologically acceptable co-solvent is selected from ethanol and isopropyl alcohol.

12. The method of claim 2, wherein the physiologically acceptable co-solvent is selected from ethanol and isopropyl alcohol.

13. The method of claim 10, wherein the physiologically acceptable co-solvent is selected from ethanol and isopropyl alcohol.

14. The method of claim 1, wherein the physiologically acceptable co-solvent is ethanol.

15. The method of claim 2, wherein the physiologically acceptable co-solvent is ethanol.

16. The method of claim 10, wherein the physiologically acceptable co-solvent is ethanol.

17. The method of claim 14, wherein the ethanol is present at a concentration of up to 5 wt %.

18. The method of claim 15, wherein the ethanol is present at a concentration of up to 5 wt %.

19. The method of claim 16, wherein the ethanol is present at a concentration of up to 5 wt %.