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(12) United States Patent (10) Patent No.: US 8,841,351 B2 Sawant (45) Date of Patent: *Sep

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(12) United States Patent (10) Patent No.: US 8,841,351 B2 Sawant (45) Date of Patent: *Sep USOO8841351B2 (12) United States Patent (10) Patent No.: US 8,841,351 B2 SaWant (45) Date of Patent: *Sep. 23, 2014 (54) POLYMERICTOPICAL COMPOSITIONS 4,938,964 A 7, 1990 Sakai et al. 4,940,579 A 7, 1990 Randen 4.954,332 A 9, 1990 Bissett et al. (71) Applicant: Stiefel Research Australia Pty Ltd., 5,081,157 A 1/1992 Pomerantz Rowville (AU) 5,082,656 A 1/1992 Hui et al. 5,304,368 A 4, 1994 Sherinov et al. (72) Inventor: Prashant Sawant, Rowville (AU) 5,436,241 A 7, 1995 Shin et al. 5,573,759 A 11/1996 Blank (73) Assignee: Stiefel Research Australia Pty Ltd., 5,658,559 A 8, 1997 Smith 5,674,912 A 10, 1997 Martin Rowville, Victoria (AU) 6,010,716 A 1/2000 Saunal et al. 6,017,520 A 1/2000 Synodis et al. (*) Notice: Subject to any disclaimer, the term of this 6,123,924 A 9/2000 Mistry et al. patent is extended or adjusted under 35 6,211,250 B1 4/2001 Tomlinson et al. U.S.C. 154(b) by 0 days. 6,582,683 B2 6/2003 Jezior 7,678,366 B2 3/2010 Friedman et al. This patent is Subject to a terminal dis 2005/0175641 A1 8, 2005 Deo et al. claimer. 2007/0196323 A1 8/2007 Zhang et al. 2007/0196325 A1 8/2007 Zhang et al. (21) Appl. No.: 13/910,158 2007/0219.171 A1 9, 2007 Lulla et al. 2008. O152603 A1 6/2008 Rudolph et al. (22) Filed: Jun. 5, 2013 2008. O17581.0 A1 7/2008 Zhang (65) Prior Publication Data FOREIGN PATENT DOCUMENTS US 2013/0267,486A1 Oct. 10, 2013 CA 1300515 5, 1992 EP O 212959 B1 3, 1993 EP O 944 398 B1 4/2004 Related U.S. Application Data WO WO 88,09185 A1 12, 1988 WO WO93/24105 A1 12, 1993 (62) Division of application No. 12/916.692, filed on Nov. WO WO95/30409 A1 11, 1995 1, 2010, now Pat. No. 8,481,591. WO WO99.49835 A1 10, 1999 WO WO O2/43739 A2 6, 2002 (51) Int. Cl. WO WO 2008/094910 A2 8, 2008 A6 IK 47/30 (2006.01) A6 IK 47/34 (2006.01) OTHER PUBLICATIONS A6 IK3I/35 (2006.01) A6 IK3I/92 (2006.01) Dictionary definition of “alcohol', downloaded from the internet A6 IK 47/32 (2006.01) Nov. 2, 2012. A6 IK3I/474 (2006.01) “Dermacryl 79 for Skin Care Formulations'. Personal Care Poly A6 IK9/00 (2006.01) mers, Specialty Products from Natl. Starch & Chem. Company, 1994, A6 IK 45/06 (2006.01) pp. 1-7. A6 IK3I/728 (2006.01) P. Sawant, et al. International J. of Pharmaceutics, 396:45-52 (2010). A6 IK3I/4164 (2006.01) Sawant, et al. Effect of Polymer Chemistry and Lipophilicity of A 6LX3/573 (2006.01) Drugs on Drug Release, Presentation 11th Pacific Polymer Confer A6 IK3I/2O3 (2006.01) ence, Dec. 6-11, 2009. A6 IK3I/7056 (2006.01) Sawant, et al. Abstract for 11th Pacific Polymer Conference, Dec. (52) U.S. Cl. 6-11, 2009. CPC ............... A61K 47/32 (2013.01); A61 K3I/351 (2013.01); A61 K31/192 (2013.01); A61 K 31/4174 (2013.01); A61 K9/0014 (2013.01): Primary Examiner — Layla Bland A61K 45/06 (2013.01); A61 K3I/728 (74) Attorney, Agent, or Firm — Dara L. Dinner; Theodore (2013.01); A61K 31/4164 (2013.01); A61 K Furman 31/573 (2013.01); A61 K3I/203 (2013.01); A6 IK3I/7056 (2013.01); A61 K47/34 (2013.01) (57) ABSTRACT USPC ....................................................... 514/772.7 (58) Field of Classification Search The present invention relates to topical antibacterial compo None sitions. The compositions comprise an antibacterial agent See application file for complete search history. Such as mupirocin, water, a polymer and a volatile solvent present in an amount of less than about 40%. The invention (56) References Cited also relates to methods of treatment by administering the compositions to a patient in need thereof, and to the use of U.S. PATENT DOCUMENTS Such compositions in the treatment of bacterial conditions. 4,393,076 A 7, 1983 Noda et al. 4.675,009 A 6/1987 Hymes et al. 4,935,241 A 6, 1990 Saitoh et al. 23 Claims, 4 Drawing Sheets U.S. Patent Sep. 23, 2014 Sheet 1 of 4 US 8,841,351 B2 IOC 3. | 6. O O SO OC: 15 SC 3CO 3S 4:O Fine (min.) Figure 1 U.S. Patent Sep. 23, 2014 Sheet 2 of 4 US 8,841,351 B2 3 O 6 O 90 12 O 15 O 18O 21 O 24 O 27 O 3 OC Time (min.) Figure 2 U.S. Patent Sep. 23, 2014 Sheet 3 of 4 US 8,841,351 B2 0.5 In Nk (1/min.) 0.4 S 0.3 N a 0.2 E. 0. 1 Š O S Š 70:30 60:40 30.70 PVPIVA Ratio Figure 3 U.S. Patent Sep. 23, 2014 Sheet 4 of 4 US 8,841,351 B2 :::: 388 Al-A 38 8: . : s: : : & 888 . & 388 8: : 88: 388 3. 8:8 (A) : .* ----- ...it 8. y is 8.388x -- $3.388 82, as 888 s 88: 888 as : i: s 88: &; :::::::::: (B) : o 8. : to : (C) Figure 4 US 8,841,351 B2 1. 2 POLYMERC TOPCAL COMPOSITIONS after topical application to leave a film on the surface of the skin. The present invention is believed to address these unmet FIELD OF THE INVENTION needs. The present invention relates to topical antibacterial com SUMMARY OF THE INVENTION positions. According to an embodiment, the present invention pro BACKGROUND OF THE INVENTION vides a topical pharmaceutical composition comprising an antibacterial agent, a polymer, water and less than about 40% Bactroban R. (2% mupirocin) ointment and Bactroban R. 10 volatile solvent. (2% calcium mupirocin) cream and ointment are marketed by According to another embodiment the present invention GlaxoSmithKline for the treatment of furuncle, impetigo and provides for a method of treating a disease, disorder or con wounds that have become infected. dition of the skin, in a mammal in need thereof, the method U.S. Pat. No. 5,082,656 (Hui et al.) describes an antibac comprises administering to said mammal, preferably a terial composition for topical administration comprising: 15 human Subject, a topical pharmaceutical composition com prising an antibacterial agent, a polymer, water and less than from about 0.5% to about 10% of an antibacterial compound, about 40% volatile solvent. from about 1% to about 30% of a non water soluble polymeric According to a further embodiment, the invention relates to composition, from about 0.5% to about 40% of a plasticizer, the use of a topical pharmaceutical composition comprising and from about 50% to about 95% of a solvent (such as an antibacterial agent, a polymer, water and less than about ethanol or isopropanol). Upon topical application of the anti 40% volatile solvent, in the preparation of a medicament for bacterial composition, the solvent will evaporate and leave a the treatment of a disease, disorder or condition of the skin. thin protective film of polymeric composition which retains In another embodiment, the invention relates to the use of the antibacterial compound against the skin. a topical pharmaceutical composition comprising an antibac U.S. Pat. No. 6,211,250 (Tomlinson et al.) describes topi 25 terial agent, a polymer, water and less than about 40% volatile cal compositions comprising at least one rate modulating Solvent, in the treatment of a disease, disorder or condition of polymer, a Volatile solvent and at least one physiologically the skin. active agent. Tomlinson discloses compositions comprising a hydrophilic polymer and a hydrophobic polymer selected to BRIEF DESCRIPTION OF THE DRAWINGS modulate the rate of release of the active agent. The compo 30 sitions comprise greater than 50% volatile solvent. A high FIG. 1 illustrates modulation of the rate of release of cal level of volatile solvent is desirable in as much as it will cium mupirocin where different variants of PVP/VA are used, solubilize the hydrophobic polymer and evaporate to leave a i.e. PVP/VA 60:40 (O), PVP/VA 70:30 (0) and PVP/VA polymeric film on the surface of the skin. However, a high 30:70 (). level of volatile solvent has the potential disadvantage of 35 FIG. 2 illustrates modulation of the rate of release of cal irritating the skin, particularly on open wounds or lesions. cium mupirocin (first order derivative) where different vari U.S. Pat. No. 6,582,683 (Jezior) describes a dermal barrier ants of PVP/VA are used, i.e. PVP/VA 60:40 (O), PVP/VA composition which comprises water, a hydrophilic polymer 70:30 (0) and PVP/VA 30:70 (). emulsion and a hydrophobic polymer emulsion. The dermal FIG.3 illustrates the rate constant (k) and release exponent barrier composition is moisture activated, and remains inert 40 (n) in connection with release of calcium mupirocin from until the hydrophobic and hydrophilic polymer emulsions compositions comprising different variants of PVP/VA, i.e. contact a Suitable Substrate Such as human skin. The dermal PVP/VA 60:40, PVP/VA 70:30 and PVP/VA 30:70. barrier composition is itself an emulsion, and may contain a FIGS. 4a-4c illustrates the rub and water resistance of the biocidal agent for treatment of a skin disorder or condition. compositions of the invention. The dermal barrier composition may also contain other active 45 agents such as Sunscreens, insect repellents and fungicides.
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