IP Library Granted Patent US 10,391,108
Granted Patent B2
US 10,391,108 · App. 15/910,978 · Granted Aug 27, 2019

Pharmaceutical tetracycline composition for dermatological use

Inventors: Xin Chen (Palo Alto, CA); Maiko C. Hermsmeier (San Jose, CA); Diana Lac (Menlo Park, CA); Douglas W. Thomas (Palo Alto, CA); Noymi Yam (Sunnyvale, CA); Akira Yamamoto (Cupertino, CA)
Assignee: BioPharmX, Inc.
A61K31/65A61K9/0014A61K9/08A61K47/02A61K47/10A61P17/10A61P31/04Y02A50/401
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Quick Facts
Patent No.
US 10,391,108
App. No.
15/910,978
Granted
Aug 27, 2019
Kind
B2
Abstract

Provided herein is a topical composition and related methods for making and using the composition. In a first aspect, the topical composition comprises minocycline, a magnesium salt, and a sulfite compound in a non-aqueous solvent. In yet another aspect, the topical composition comprises a tetracycline-class drug, a source of magnesium, a monohydric aliphatic alcohol, and a polyol, wherein (i) the ratio between the monohydric aliphatic alcohol and the propylene glycol is in the range of 1:1 to 99:1 by weight and (ii) the tetracycline-class drug is dissolved in the topical composition.

Claims (42)

1. A topical composition, comprising:

minocycline,

a divalent cation,

a sulfite compound, and

a solvent;

wherein

the minocycline is dissolved in the composition; and

the relative concentration of 4-epi-minocycline in the composition is less than 5.0% after storage at 40° C. in a sealed glass vial for 4 weeks.

2. The topical composition of claim 1 , wherein the relative concentration of 4-epi-minocycline increases less than 1.00% per week when stored at 40° C. in a sealed glass vial for 4 weeks.

3. The topical composition of claim 1 , wherein the relative concentration of 4-epi-minocycline is 0.50% to 1.00% prior to storage and increases 0.20% to 0.40% when stored at 40° C. in a sealed glass vial for 4 weeks.

4. The topical composition of claim 1 , wherein the relative concentration of 4-epi-minocycline is 0.50% to 1.00% prior to storage and increases 0.20% to 0.40% when stored at 40° C. in a sealed glass vial for 4 weeks.

5. The topical composition of claim 1 , wherein

the solvent comprises ethanol,

the divalent cation is a magnesium cation, and

the composition comprises less than 5% water as measured by Karl Fischer titration.

6. The topical composition of claim 5 , wherein the composition comprises less than 3% water as measured by Karl Fischer titration.

7. The topical composition of claim 5 , wherein the composition comprises less than 2% water as measured by Karl Fischer titration.

8. The topical composition of claim 5 , wherein the composition comprises less than 1% water as measured by Karl Fischer titration.

9. The topical composition of claim 5 , wherein the composition comprises 0.5% to 1.0% water as measured by Karl Fischer titration.

10. The topical composition of claim 1 , wherein the solvent comprises a monohydric aliphatic alcohol and a polyol.

11. The topical composition of claim 10 , wherein the ratio of the monohydric aliphatic alcohol to the polyol is in the range of 1:1 to 99:1 by weight.

12. The topical composition of claim 10 , wherein the ratio of the monohydric aliphatic alcohol to the polyol is in the range of 2:1 to 10:1 by weight.

13. The topical composition of claim 1 , wherein the molar ratio of the divalent cation to the minocycline is in a range of about 2:1 to 100:1.

14. The topical composition of claim 10 , wherein the monohydric aliphatic alcohol is selected from the group consisting of ethanol, isopropanol, propyl alcohol, tert-butyl alcohol, and combinations thereof.

15. The topical composition of claim 10 , wherein the monohydric aliphatic alcohol is ethanol.

16. The topical composition of claim 10 , wherein the polyol is a C3-C8 diol or a triol.

17. The topical composition of claim 16 , wherein the polyol is propylene glycol.

18. The topical composition of claim 1 , wherein the sulfite compound is a sulfite, bisulfite, pyrosulfite, or metabisulfite.

19. The topical composition of claim 18 , wherein the sulfite compound is an inorganic sulfite salt comprising an inorganic cation selected from sodium, potassium, calcium and magnesium.

20. The topical composition of claim 18 , wherein the sulfite is selected from the group consisting of sodium sulfite, sodium bisulfite, and sodium meta-bisulfite.

21. The topical composition of claim 1 , comprising from about 0.005% to about 3.0% by weight of the sulfite compound.

22. The topical composition of claim 1 , comprising from about 0.1% to about 4% by weight of the minocycline.

23. The topical composition of claim 1 , further comprising an essential oil.

24. The topical composition of claim 23 , comprising 0.01 to 5 weight percent of 1,8-cineole.

25. The topical composition of claim 1 , wherein the composition is not an emulsion and/or does not comprise nanoparticles or microparticles.

26. The topical composition of claim 1 , having an effective pH of 3-6 when mixed with water in a ratio of 1:9 by weight.

27. The topical composition of claim 1 , wherein the composition exhibits no significant change in color after aging for 4 weeks at 40° C. in a sealed container.

28. The topical composition of claim 27 , wherein no significant color change is a color change of less than 20 in distance in 3-dimensional RGB space where each value is measured on a 0-255 range and distance is calculated in 3-dimensional RGB space according to the following formula: distance RGB =((ΔR) 2 +(ΔG) 2 +(ΔB) 2 ) 0.5 .

29. The topical composition of claim 1 , wherein the composition is hydrophilic.

30. A method for treating an active dermatological inflammation or infection comprising applying the topical composition of claim 1 to an inflamed or infected area of skin of a human at least once daily for a period of at least 1 month.

31. The method of claim 30 wherein the active dermatological inflammation or infection is acne.

32. The method of claim 30 wherein the active dermatological inflammation or infection is rosacea.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 11, 2024
From: TIMBER PHARMACEUTICALS, INC.; TIMBER PHARMACEUTICALS, LLC; BIOPHARMX, INC.
To: LEO PHARMA A/S
Reel/Frame 066782/0409 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 22, 2024
From: TIMBER PHARMACEUTICALS, INC.; TIMBER PHARMACEUTICALS, LLC; BIOPHARMX, INC.
To: LEO PHARMA A/S
Reel/Frame 066660/0001 →
SECURITY INTEREST Recorded Feb 11, 2020
From: BIOPHARMX, INC.
To: TIMBER PHARMACEUTICALS LLC
Reel/Frame 051789/0070 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 28, 2018
From: CHEN, XIN; HERMSMEIER, MAIKO; LAC, DIANA; THOMAS, DOUGLAS W.; YAM, NOYMI; YAMAMOTO, AKIRA
To: BIOPHARMX, INC.
Reel/Frame 045379/0613 →
Continuity (8)
Continuation 15077858 · Mar 22, 2016
Provisional Application 62304119 · Mar 4, 2016
Provisional Application 62279654 · Jan 15, 2016
Provisional Application 62266650 · Dec 13, 2015
Provisional Application 62251001 · Nov 4, 2015
Provisional Application 62245262 · Oct 22, 2015
Provisional Application 62137216 · Mar 23, 2015
Related Publication 20180185394A1 · Jul 5, 2018
Cited By (1)
US 12,661,407