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(12) United States Patent (10) Patent No.: US 8,349,297 B2 Brown Et Al

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(12) United States Patent (10) Patent No.: US 8,349,297 B2 Brown Et Al US008349297B2 (12) United States Patent (10) Patent No.: US 8,349,297 B2 BrOWn et al. (45) Date of Patent: Jan. 8, 2013 (54) TOPICAL FORMULATIONS FOREIGN PATENT DOCUMENTS AU 198664.695 5, 1988 (75) Inventors: Marc Barry Brown, Watford (GB); GB 2188844 10, 1987 JP O1230514 9, 1989 Stuart Allen Jones, Blackheath (GB) JP O8291.050 11, 1996 WO WO 88,0918.5 12, 1988 (73) Assignee: Medpharm Limited, Guilford (GB) WO WO95/15151 6, 1995 WO WOOO.38658 T 2000 (*) Notice: Subject to any disclaimer, the term of this WO WOOOf 45795 8, 2000 patent is extended or adjusted under 35 WO WOO1? 43722 6, 2001 U.S.C. 154(b) by 812 days. OTHER PUBLICATIONS (21) Appl. No.: 12/067,004 “Miscible” in Merriam-Webster's Collegiate Dictionary, 10th edi tion, Merriam-Webster, Inc.: Springfield, Mass., 1993, pp. 743.* Brambilla et al. (1999) “Modulation of Aerosol Clouds Produced by (22) PCT Filed: Sep. 14, 2006 Pressurized Inhalation Aerosols.” Int. J. Pharmaceutics 186:53-61. Hadgraft, J. (2004) “Skin Deep.” Eur: J. Pharm. Biopharm. 58:291 (86). PCT No.: PCT/GB2OO6/OO3408 299. International Search Report, Corresponding to International Appli S371 (c)(1), cation No. PCT/GB2006/003408, Mailed Feb. 27, 2007. (2), (4) Date: Jul. 16, 2008 Moser et al. (2001) "Supersaturation: Enhancement of Skin Penetra tion and Permeation of a Lipophilic Drug.” Pharm. Res. 18(7):1006 (87) PCT Pub. No.: WO2007/031753 1011. Moser et al. (May 2001) “Permeation Enhancement of a Highly PCT Pub. Date: Mar. 22, 2007 Lipophilic Drug Using Supersaturated Systems.” J. Pharm. Sci. 90(5):607-616. (65) Prior Publication Data Moser et al. (2001) Stabilization of Supersaturated Solutions of a Lipophilic Drug for Dermal Delivery. Int. J. Pharm. 224:169-176. US 2009/O191271 A1 Jul. 30, 2009 Ranade, V.V. (1995)“Transdermal Drug Delivery.” In; Drug Delivery Systems, CRC Press, New York, pp. 177-208. (30) Foreign Application Priority Data Thomas et al. (Aug. 2004) “The Transdermal Revolution.” Drug Disc. Today 9(16):697-703. Sep. 14, 2005 (GB) ................................... 0518769.5 Ting et al. (2004) “Review of Traditional and Novel Modalities that Enhance the Permeability of Local Therapeutics Across the Stratum (51) Int. Cl. corneum,' Int. J. Dermatol. 43:538-547. A6 IK 9/12 (2006.01) Vervaet et al. (1999) “Drug-Surfactant-Propellant Interactions in HFA-Formulations. Int. J. Pharm. 186:13-30. (52) U.S. Cl. ......................................................... 424/45 Yong-Hong Liao (Jul. 2002) "Studies on the Stabilization and For (58) Field of Classification Search ..................... 424/45 mation of Proteins for Airway Delivery.” PhD. Thesis, University of See application file for complete search history. London, Department of Pharmacy, King's College London. (56) References Cited * cited by examiner U.S. PATENT DOCUMENTS Primary Examiner — James H. Alstrum-Acevedo 4,752.466 A 6, 1988 Saferstein et al. (74) Attorney, Agent, or Firm — Greenlee Sullivan P.C. 4,863,721 A 9, 1989 Becket al. 5,776.432 A 7, 1998 Schultz et al. (57) ABSTRACT 6,123,924 A 9/2000 Mistry et al. 6,325,990 B1 12/2001 Laurent Saturated, monophasic Solutions of drug in a solvent and 6.432,415 B1 8, 2002 Osborne et al. propellant mixture, together with a film-forming agent, 2003. O152611 A1 8, 2003 Illel et al. 2003,0224053 A1 12/2003 Fotinos et al. exhibit transdermal diffusion fluxes greater than those pre 2004/O184994 A1 9, 2004 DeStefano et al. dicted by Fick's law when applied topically. 2004/0213744 A1 10, 2004 Lulla et al. 2011/0002856 A1* 1/2011 Holland et al. ................. 424/45 33 Claims, 14 Drawing Sheets U.S. Patent US 8,349,297 B2 Soluble & Insoluble Fig.1 U.S. Patent Jan. 8, 2013 Sheet 2 of 14 US 8,349,297 B2 20%PVP Soluble Insoluble s OE-FA. 0%PWF 20%BDPt Fig.2 U.S. Patent Jan. 8, 2013 Sheet 3 of 14 US 8,349,297 B2 10%VP Soluble & Insoluble O'BMW Fig.3 U.S. Patent Jan. 8, 2013 Sheet 4 of 14 US 8,349,297 B2 -- 30 SHOT, 10% EtOH BDP 4000 --20 SHOT, 10% EtOHBDP - 10 SHOT, 10% EtOH BDP 500 - 5 SHOT, 10% EtOHBDP S. 5 4G - 5 SHOT 10%EtOH BDP 3. a BOP Crear U.S. Patent Jan. 8, 2013 Sheet 5 of 14 US 8,349,297 B2 450, ran 5 Shot 20% to '' -- to shot 10%Eoh 350.) 30, 250.0 200, SO, 1. 5, , O.S s 2 2, 3. 3.5 4. 4.5 Time (h) Fig.6 3S.O. -- BMW Spray, 20 shots at ESW Creat 2.23 G SO. 50. O ,S 1.5 2 2.5 3 3.5 di 4.5 Time (h) Fig.7 U.S. Patent Jan. 8, 2013 Sheet 6 of 14 US 8,349,297 B2 f000 90.0 80.0 0.0 60.0 500 400 30, 20,0 -E-BMW Spray, 5 shots 0. -- BMW Mousse O.0 O OS 5 2.5 3 3.5 4. 4.5 Time (h) Fig.8 9000 es. 6:50 PWAPWP 700.0 800,0 5000 400,0 300,0 200,0 O00 0.0 O OS t 1.5 2.5 3 3.5 4. 4.5 Time (h) Fig.9 U.S. Patent Jan. 8, 2013 Sheet 7 of 14 US 8,349,297 B2 4500 -- Saturated nor OOO Wolatile -- Subsaturated 900 -A-Saturated volatile 30), 25. 200.0 SCO OOO 500 O O.S s 2. 2S 3. 35 d see Sisted PEG -- G& EtOx40, No plastic suru is PEG, 40x or SS, CSxSO --- - { t s s S. SS s d. Time hrs) Fig.11 U.S. Patent Jan. 8, 2013 Sheet 8 of 14 US 8,349,297 B2 Terrary Flot. Formulation 22 Sibi w Precipitated it. it's E. Ei. E. St. & S sy. E. sits 3. E3 s risisi. Excipient%3 U.S. Patent Jan. 8, 2013 Sheet 9 of 14 US 8,349,297 B2 ---O.O13% BMW E 300 -- 0.500% BMW 250- of 1.00% BMW | SS 150 is 100 Sg o 50O 6 O ( 0.03% BMW y: 60.095x+ 46492 w Rat (.9967 5 O 0.500% BMW 4. O A 1.00% BMW y = 42.199x.- 0.0188 x Sat EtOH Rs 0.8106 3 O aw y at 23.874x + 11.291 2 O Rs 0.6924 O y in 18488x -3.1394 R’s 0.9979 O ------w WWWWom vow VWWam WWM wam War. --- roo axa)---Wmm wax mm. -Wux-aa MW WWamm W U.S. Patent Jan. 8, 2013 Sheet 10 of 14 US 8,349,297 B2 Ternary Plot, F22 YS SA Fixed at 2%, 25 Excipient s Copowidone S-630 19 Jul 06 80 HFA o 5 10 15 2O 25 Excipient O Soluble o Precipiated Fig. 14 U.S. Patent Jan. 8, 2013 Sheet 11 of 14 US 8,349,297 B2 35.0. -- Spray X 30.0 - -- Spray Y S mir-Spray Z. mix-Diprosone cream s 5 250 Y . "es S} 8 20.0 - 22 315.0 - S OO . s E 3 5.0 - 2 s/ 9 2 S O.O wo 25- aro O 1 2 3 4. 5 U.S. Patent Jan. 8, 2013 Sheet 12 of 14 US 8,349,297 B2 Ternary Plot, F22 HFA (%) Ethanol Fixed at 10%, 10 Excipient = PVP K90 O . , \, a . dy of o \ o, R. A '. ', y * , a , a , , *. f o / /Soluble / / / 5 / / / / / / bone O Precipiated Fig. 16 U.S. Patent Jan. 8, 2013 Sheet 13 of 14 US 8,349,297 B2 5,00 4,50 4,00 y = -0.3056x +3.4968 3,50 - R2 = 0.7195 3.00 - 2,50 - 2.00 150 OO O,50 0.00 O 2 3 4. 5 6 7 8 9 Distance (cm) Fig. 17 y = 0.3394x + 1.809 R = 0,5184 Number of Shots Fig. 18 U.S. Patent Jan. 8, 2013 Sheet 14 of 14 US 8,349,297 B2 30,00 . ... MDA -- BMWGel 2 5. O O 20.00 15.00 “"“www. --- 10.00 5.00 0.00 morowomorrow-moon rooroorooroorooroo O 10 2O 30 40 50 60 70 8O Time (h) Fig. 19 US 8,349,297 B2 1. 2 TOPCAL FORMULATIONS connective tissue; and 3) the subcutaneous fat beneath the dermis. The physiological function of the Stratum corneum, CROSS-REFERENCE TO RELATED the outermost and non-viable layer of the skin, is to act as a APPLICATIONS protective barrier for the body. The Stratum corneum’s inter cellular lipids comprise ceramides, cholesterols, cholesterol This application is a 35 U.S.C. 371 National Phase Appli esters, and free fatty acids, whose organisation and unique cation of PCT/GB2006/003408, filed Sep. 14, 2006, which chemical composition create a high degree of water imper application claims benefit of GB 0518769.5, filed Sep. 14, meability. It is these lipid lamellae that contribute greatly to 2005. 10 the epidermal permeability barrier, both to water and to other The present invention relates to formulations for topical permeates (Ting et al., 2004). drug delivery, and methods for their use and manufacture. In order for therapeutic quantities of drug to penetrate the The administration of therapeutic compounds either skin, the barrier properties of the Stratum corneum must be locally to the skin, or into the systemic circulation after pas overcome. The Stratum corneum exhibits selective perme sage through the skin, offers numerous potential advantages 15 ability and allows only relatively lipophilic compounds with over oral or parenteral drug delivery. These include the avoid a molecular weight below 400 Daltons to pass.
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