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(12) Patent Application Publication (10) Pub. No.: US 2010/0158993 A1 Spann-Wade Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2010/0158993 A1 Spann-Wade Et Al US 20100158993A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2010/0158993 A1 Spann-Wade et al. (43) Pub. Date: Jun. 24, 2010 (54) TOPICAL GEL COMPOSITIONS A61O 1704 (2006.01) A6IR 9/14 (2006.01) (75) Inventors: Monique Spann-Wade, A 6LX 9/27 (2006.01) Chesterfield, MO (US); Anthony A6II 3/545 (2006.01) Ward, St. Louis, MO (US) A63L/436 (2006.01) A63L/455 (2006.01) Correspondence Address: A6II 3/423 (2006.01) FROST BROWN TODD, LLC A63L/452 (2006.01) 2200 PNCCENTER, 201 E. FIFTH STREET A63L/407 (2006.01) CINCINNATI, OH 45202 (US) A6II 3/405 (2006.01) A63L/92 (2006.01) (73) Assignee: ISW Group, Inc., St. Louis, MO A6II 3/196 (2006.01) (US) A6II 3/165. (2006.01) A6II 3L/245 (2006.01) (21) Appl. No.: 12/643,582 (52) U.S. Cl. ........... 424/450; 514/532: 514/163; 424/60; 424/484: 514/226.5: 514/291; 514/352: 514/375; (22) Filed: Dec. 21, 2009 514/404: 514/413: 514/420; 514/570; 514/567; Related U.S. Application Data 514/575; 514/535 (63) Continuation of application No. 1 1/361.384, filed on (57) ABSTRACT Feb. 24, 2006, now abandoned. Topical alcoholic gel compositions are disclosed that are O O useful for delivering therapeutic levels of an NSAID to target Publication Classification in and below the skin. The compositions comprise a topically (51) Int. Cl. active drug, an alcoholic solvent, a polymeric thickener, and A6 IK 3L/26 (2006.01) optionally a keratolytic agent. In one embodiment, excellent A6IP 7/00 (2006.01) Viscosity for dermal application is attained without the need A6IP 7/06 (2006.01) of a step for neutralizing the pH of the composition. Alcoholic A6 IK3I/60 (2006.01) and alcohol-free topical compositions comprising an NSAID A6IP 7/2 (2006.01) prodrug are also disclosed. The compositions are particularly A6 IK S/37 (2006.01) useful for the treatment of pseudofolliculitis barbae. Patent Application Publication Jun. 24, 2010 Sheet 1 of 15 US 2010/0158993 A1 & r year -- SS S. NS e N s NNNN S N 2 SSS s É NSN S. NSN NNN N N NN N s s s s s s s Asoos.A Patent Application Publication Jun. 24, 2010 Sheet 2 of 15 US 2010/0158993 A1 N : N < i Ne N g i S 2 - i. Ns 5 2 N. | N 2 s SS a Patent Application Publication Jun. 24, 2010 Sheet 3 of 15 K?soos?AHdSAVS-uoNpubVSJOsuo??soduI0O 000€Z 000ZZ 000IZ 0000Z 0006|| 0008|| Asoo’s A Patent Application Publication Jun. 24, 2010 Sheet 4 of 15 US 2010/0158993 A1 K?soos?ApozitetitioNºñue?O }}{}{} (eAloe 9/, Patent Application Publication Jun. 24, 2010 Sheet 5 of 15 US 2010/0158993 A1 ç9.InãIH Patent Application Publication Jun. 24, 2010 Sheet 6 of 15 US 2010/0158993 A1 www.rwww. w - as:SSSSSSS:s yer w US 2010/0158993 A1 a-a-a-----------------wasar-i-r-ir-ir-irrs' were re-rmian-ou...w----------rr-i-i-tra lf s s r Ny. Patent Application Publication Jun. 24, 2010 Sheet 8 of 15 US 2010/0158993 A1 3 E. Y-Vlaawa------way tit-s---aufravitva... -------- st runsw-spa sepaw-past. J. art, Awwa.h4 Awwamwave-mily Patent Application Publication Jun. 24, 2010 Sheet 9 of 15 US 2010/0158993 A1 | | || } |-| | || ~~~~-;--~~~~ ~~~*=~~~~*~*~-------------+---+---+---+-***__N_3_(_)~,~~~~~~~~ •r-- | ... raysorworm wasmashwar khakf| | | | || ?| Auertti8 'lu-klu-r-------& 3 R B re-rrin-rrevailirukui'i'iwakil-rialsis $14: 'Nisually Patent Application Publication Jun. 24, 2010 Sheet 10 of 15 US 2010/0158993 A1 WWW land live pala Malaman-my-wiswt-aw asaws: - www. -----4---bram-rrrr's lumirr 1-Tw-WWYA All lseyraxillamusar-warm A-4s fear 1-wr Wh" alry. A w.xls) was s' ...livi-rra- wn tarr' ...tv'"a a 8 : 3 Patent Application Publication Jun. 24, 2010 Sheet 11 of 15 US 2010/0158993 A1 *-___----------------~--~~~~* **w*x-------~----*** Patent Application Publication Jun. 24, 2010 Sheet 12 of 15 US 2010/0158993 A1 0I0JnãIH (0,9Hd)HOBNo wer (It).0 L J O %) in Ip 0. Patent Application Publication Jun. 24, 2010 Sheet 13 of 15 US 2010/0158993 A1 II?InãIH (e)0 LJ.0%) in Ipod Patent Application Publication Jun. 24, 2010 Sheet 14 of 15 US 2010/0158993 A1 ZI0InáH HO(†)HND.(0'SHd) (Ae (I? 96) in Ip 0.Id Patent Application Publication Jun. 24, 2010 Sheet 15 of 15 US 2010/0158993 A1 | 9.InãIH?I (t) 0 L J O %) in Ip 0.Id US 2010/0158993 A1 Jun. 24, 2010 TOPCAL GEL COMPOSITIONS profen), and another group of NSAIDs consists of acetic acid derivatives (e.g., indomethacin). CROSS-REFERENCE TO RELATED 0008 NSAIDs can cause gastric ulcers and bleeding on APPLICATION long-term oral use. A goal of topical administration of NSAIDs is to deliver therapeutically effective levels of drug 0001. This application claims priority to U.S. Provisional to the local target (e.g., nociceptors and inflammatory cells in Patent Application No. 60/658,084, filed Mar. 3, 2005: U.S. the skin) while bypassing the stomach and preventing sys Provisional Patent Application No. 60/681,102, filed May 13, temic delivery. 2005; and U.S. Provisional Patent Application No. 60/690, 0009. Unfortunately, NSAIDs are often not well absorbed 201, filed Jun. 14, 2005, each of which are hereby incorpo when administered topically. Those topical formulations that rated by reference in their entirety. do provide some absorption through the skin can result in substantial systemic delivery and often fail to provide thera TECHNICAL FIELD peutic levels in the skin. 0002 The present invention relates to topical composi 0010. In addition, acute inflammation and pain are often tions, particularly topical compositions, which are used for treated by the topical administration of a counterirritant. In applying pharmaceutical agents to the skin. The invention this regard, a widely used agent is methyl salicylate, which is also relates to compositions for treating pain resulting from often applied to the skin in the form of an ointment or cream local stimulation of nociceptors in skin, bones, joints, and and which elicits a soothing, mildly analgesic effect. How muscles and in skin disorders wherein inflammation is a ever, methyl salicylate suffers from the disadvantage that it component of the pathogenesis. An example of Such an possesses an odor, which under certain circumstances, and to inflammatory skin disorder that relates to the present inven certain individuals, can be regarded as unpleasant. tion is pseudofolliculitis barbae. (0011 U.S. Pat. No. 4,185,100 entitled, “Topical Anti-In flammatory Drug Therapy, describes a method of topical FIELD OF THE INVENTION treatment of an inflammatory condition of the skin compris ing applying to the affected area a nonsteroidal anti-inflam 0003. The pathogenesis of a wide variety of skin disorders matory agent and concurrently a topically active anti-inflam involves an inflammatory process. Often, such disorders matory corticosteroid. These agents are applied in a involve inflammatory cells (e.g., polymorphonuclear neutro dermatologically-acceptable, topical vehicle selected from phils and lymphocytes) infiltrating the skin with no overt or the group consisting of creams, gels, ointments, powders, known infectious etiology. Symptoms of inflammatory skin aerosols and solutions Suitable for topical administration. conditions generally include erythema (redness), edema 0012 Kyuki et al., “Anti-Inflammatory Effect of (Swelling), pain, pruritus, increased surface temperature and Diclofenac-Sodium Ointment (Cream) in Topical Applica loss of function. tion.” Japan J. Pharmacol. 33, 121-132 (1983), describes the 0004 While a range of treatments have been developed for anti-inflammatory effect of a diclofenac-sodium. Ointments inflammatory skin conditions, none are completely effective were prepared with three kinds of bases: lithophilic, emulsion or free of adverse side effects. Treatments for different (cream) and gel bases and their anti-inflammatory effects inflammatory skin conditions typically include topical or oral were compared. The cream base was reported by Kyaki et al. steroids (e.g., for various types of eczema, acne, and to have the most potent effect. erythema multiforme); ultraviolet light (e.g., for nummular 0013 EP Published Patent Application EP 0151953, eczema and mycosis fungoides); antibiotics, and other anti entitled “Topical Drug Release System.” describes on pages inflammatory therapies. 10-11 an ibuprofen CARBOPOL(R) gel system containing 0005 Corticosteroids have the greatest importance for the ibuprofen, propylene glycol, water, CARBOPOL(R) 940 treatment of inflammatory skin disorders. Weak to medium (polyacrylic acid polymer) and diisopropanolamine, as an strong corticosteroids (e.g., nonfluorinated derivatives of illustrative example of a pharmaceutical composition for per hydrocortisone) are mainly employed for the therapy of cutaneous absorption by topical application made in two liq inflammatory, allergic and pruritic skin disorders. While uid drug-containing phases, which are to be mixed together in short-term treatment (a few days or weeks) with oral steroids situ just before use to form a Supersaturated drug-containing is relatively safe, long-term treatment (more than 3 months) gel. The EPO application discloses a nonalcoholic gel system may cause undesirable side effects including Cushing's Syn for delivering ibuprofen topically. drome, skin thinning, and increased Susceptibility to infec O014 U.S. Pat. No. 5,093,133, entitled “Method for Per tion. In addition, improvements may be delayed, such as with cutaneous Delivery of Ibuprofen Using Hydroalcoholic Gel.” the various acne treatments, lasting several months. describes a hydroalcoholic gel comprising ibuprofen, a 0006. There are also a variety of agents commonly used in hydroxypropylcellulose or polyacrylic acid polymer, with medical practice which are nonnarcotic and nonsteroidal, but propylene glycol being an optional but preferred ingredient.
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