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Backing Material Packaging Liner US 20120277695A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2012/0277695A1 Cottrell et al. (43) Pub. Date: Nov. 1, 2012 (54) TRANSDERMAL DELIVERY PATCH (30) Foreign Application Priority Data (76) Inventors: Jeremy Cottrell, Caulfield South Mar. 30, 2010 (US) .................................... 603.190O2 (AU); Giacinto Gaetano, South Melbourne (AU); Mahmoud Publication Classification El-Tamimy, Meadow Heights (51) Int. Cl. (AU); Nicholas Kennedy, Boronia A6M 35/00 (2006.01) (AU); Paul David Gavin, B29C 39/38 (2006.01) Chadstone (AU) A6II 47/32 (2006.01) (21) Appl. No.: 131501,499 (52) U.S. Cl. ....................... 604/304: 514/772.4; 264/330 (22) PCT Filed: May 18, 2010 (57) ABSTRACT (86). PCT No.: PCT/AU1O/OO58O A composition Suitable for use in a transdermal delivery patch S371 (c)(1), for administration of an opioid, the composition comprising a (2), (4) Date: Apr. 12, 2012 phosphate compound of tocopherol and a polymer carrier. Backing material Matrix film Packaging liner is is: 8&ssar & : 88 & 3: s: 3 & M 2332 - is is is sis: 8:s - is is assissists m Patent Application Publication Nov. 1, 2012 Sheet 1 of 6 US 2012/0277695A1 Backing material - Matrix film t Packaging liner tax sea is is as - - - - - - - i8 is: as sawk: ---- assassisi Etes Figure 1 Patent Application Publication Nov. 1, 2012 Sheet 2 of 6 US 2012/0277695A1 Hurrar full thickness skin s 3D or matrix overnight drying -- matrix accelerated drying Szoo 5 100 E O O O O Time (h Figure 2 Patent Application Publication Nov. 1, 2012 Sheet 3 of 6 US 2012/0277695A1 matrix rt matrix glue kd O Time (h) Figure 3 Patent Application Publication Nov. 1, 2012 Sheet 4 of 6 US 2012/0277695A1 4 -- matrix -- matric OCCluded 2 10 Time thr) Figure 4 Patent Application Publication Nov. 1, 2012 Sheet 5 of 6 US 2012/0277695A1 200 18O ! -(-10 mg (10:5:1), O.N., dry -O-10 mg (14:5:1), O.N. dry 160 * 5 mg (14:5:1), Acc. dry 140 -(-5 mg (14:10:1), Acc. Dry, Duro-Tak glue u 120 -- 100 --- Figure 5 Patent Application Publication Nov. 1, 2012 Sheet 6 of 6 US 2012/0277695A1 3O.O -8-10 mg 10:5:1) re-smg (14.5:1) 25.O. " *&^S ring 4:10:2), rapid dry, adhesive Hours Figure 6 US 2012/0277695A1 Nov. 1, 2012 TRANSIDERMAL DELIVERY PATCH MW 360,000 Da), polysiloxanes and polymethyl methacry late (e.g. Eudragit E100). The composition, or matrix layer, TECHNICAL FIELD may comprise a polymer carrier in an amount of from about 0001. The present invention relates to a transdermal deliv 20% w/w up to about 90% w/w, from about 30% w/w up to ery patch for administration of therapeutic compounds. More about 80% w/w, from about 55% w/w up to about 65% w/w, specifically, the present invention relates to a transdermal of the total weight of the composition, or matrix layer. delivery patch for administration of opioids. 0014. The polymer carrier may also comprise inert carrier components selected from the group consisting of anti-tack BACKGROUND ing agents, tackifiers, and plasticizers. 0002. In this specification where a document, act or item 0015 Inert carrier components may be present in the com of knowledge is referred to or discussed, this reference or position, or matrix layer, in an amount of from 0.001% w/w discussion is not an admission that the document, actor item up to about 50% w/w, up to about 40% w/w, from up to about of knowledge or any combination thereof was at the priority 30% w/w, of the total weight of the composition, or matrix date, publicly available, known to the public, part of common layer. general knowledge; or known to be relevant to an attempt to 0016. A third aspect provides a transdermal delivery patch solve any problem with which this specification is concerned. for administration of an opioid comprising (i) a backing layer, 0003 Drug delivery is the method or process of adminis tering a pharmaceutical compound to achieve a therapeutic and (ii) a matrix layer, which comprises a phosphate com effect in humans and animals. pound oftocopherol and a polymer carrier (as defined above), 0004 Drug delivery technologies have been developed to and an opioid. improve bioavailability, safety, duration, onset or release, of 0017. A fourth aspect provides use of a matrix patch for the pharmaceutical compound. transdermal delivery of an opioid, the matrix patch compris 0005. When developing drug delivery technologies, prob ing (i) a backing layer and (ii) a matrix layer, which comprises lems likely: to be encountered include compatibility of the a phosphate compound of tocopherol and a polymer carrier drug delivery system and the pharmaceutical compound, (as defined above), and an opioid. maintaining an adequate and effective duration, potential for 0018. The opioid may be selected from the group consist side effects, and meeting patient convenience and compli ing of morphine, codeine or thebaine; hydromorphone, ance. As a consequence, many drug delivery technologies fall hydrocodone, oxycodone, oxymorphone, desomorphine, short of desired improvements and requirements. diacetylmorphine (heroin), nicomorphine, dipropanoylmor 0006. Accordingly, there is still a need for alternate drug phine, benzylmorphine or ethylmorphine; fentanyl, pethi delivery systems that effectively deliver drugs. dine, methadone, tramadol or dextropropoxyphene; endor phins, enkephalins, dynorphins, or endomorphins. SUMMARY 0019. The opioid may also be selected from the group 0007. It has surprisingly been found that opioids can be consisting of opioid receptor agonists including morphine, effectively administered using a transdermal delivery patch. depomorphine, etorphine, heroin, hydromorphone, oxymor 0008 According to a first aspect, there is provided a com phone, levorphanol, methadone, levomethadyl, meperidine, position suitable for use in a transdermal delivery patch for fentanyl, Sufentanyl, alfentanil, codeine, hydrocodone, oxy administration of an opioid, the composition comprising a codone, and mixtures thereof opioid receptor antagonists phosphate compound of tocopherol and a polymer carrier. including naloxone and naltrexone; opioid receptor mixed 0009. In one embodiment, the transdermal delivery patch agonist-antagonists including buprenorphine, nalbuphine, is a matrix patch. butorphanol, pentazocine, and mixtures thereof, and, ethylke 0010. A second aspect provides use of a phosphate com tocyclazocine. pound oftocopherol and a polymer carrier as a matrix layer in 0020. The opioid may also be selected from the group a transdermal delivery patch for administration of an opioid. consisting of codeine, morphine, thebaine and oripavine; 0011. The phosphate compound of tocopherol may be diacetylmorphine (heroin), dihydrocodeine, hydrocodone, selected from the group consisting of mono-(tocopheryl) hydromorphone, nicomorphine, desmorphine, ethylmor phosphate, mono-(tocopheryl)phosphate monosodium salt, phine, dipropanoylmorphine, oxycodone and oxymorphone; mono-(tocopheryl)phosphate disodium salt, mono-(toco fentanyl, alphamethylfentanyl, alfentanil, Sufentanil, pheryl)phosphate monopotassium salt, mono-(tocopheryl) remifentanil, carfentanyl and ohmefentanyl; pethidine (mep phosphate dipotassium salt, di-(tocopheryl)phosphate, di eridine), ketobemidone, MPPP, allylprodine, prodine and (tocopheryl)phosphate monosodium salt, di-(tocopheryl) PEPAP; propoxyphene, dextropropoxyphene, dextromora phosphate monopotassium salt, or a mixture thereof. These mide, bezitramide, piritramide, methadone, dipipanone, phosphate compounds may be derived from the alpha, beta, levomethadyl acetate (LAAM), difenoxin, diphenoxylate and gamma or delta form oftocopherol, or a combination thereof. loperamide, dezocine, pentazocine and phenazocine; 0012. The composition, or matrix layer, may comprise a buprenorphine, dihydroetorphine and etorphine; butorpha phosphate compound of tocopherol in an amount within the nol, nalbuphine, levorphanol and levomethorphan; lefe range of about 0.01% w/w to about 10% w/w, about 0.1% w/w tamine, meptazinol, tilidine, tramadol and tapentadol; to about 5% w/w, about 0.5% w/w to about 2% w/w or to nalmefene, naloxone and naltrexone; and pharmaceutically about 3% w/w, of the total concentration of the matrix layer. acceptable salts, prodrugs, or derivatised compounds thereof. In one embodiment, the phosphate compound oftocopherol is 0021. In a preferred embodiment, the opioid is oxycodone present in an amount of about 1% w/w to about 1.5% w/w of or dihydrohydroxycodeinone (oxycodone base). the total concentration of the matrix layer. 0022. The opioid may be present in an amount of from 0013 The polymer carrier may comprise natural and syn about 0.1% w/w up to about 30% w/w, up to about 20% w/w, thetic polymers, co-polymers, or terpolymers. Preferred up to about 10% w/w, of the total concentration of the com polymer carriers that are Suitable for use in the composition, position, or matrix layer. In one embodiment, the composi or matrix layer, include polyvinyl pyrrolidone (e.g. PVP K90, tion, or matrix layer, will have an opioid concentration of US 2012/0277695A1 Nov. 1, 2012 about 4.5% w/w to about 5.5% w/w of the total concentration of the composition, or matrix layer. -continued 0023 Preferably the backing layer is occlusive. 0024. A fifth aspect provides a method for preparing a (I) transdermal delivery patch for administration of an opioid comprising the steps of 0025 (i) combining a polymer carrier and optional inert carrier components with a suitable solvent; 0026 (ii) combining (i) with a dispersion comprising a phosphate compound of tocopherol and an opioid; 0027 (iii) stirring (ii) until complete homogenisation is achieved; 0028 (iv) placing (iii) in a mould comprising a suitable 8-tocopherol H H CH backing layer, and 8-tocotrienol 0029 (V.) drying the compositions in the mould by heat ing them up to about 90° C. for about 0.5 to about 24 hours. Preferably, the drying is conducted at a tempera 0033. In the present invention, tocopherol in any of the ture of 75° C. four forms may be used. The alpha form of tocopherol is preferred. DETAILED DESCRIPTION 0034.
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