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United States Patent (19) 11 Patent Number: 4,746,509 Haggiage Et Al

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United States Patent (19) 11 Patent Number: 4,746,509 Haggiage Et Al United States Patent (19) 11 Patent Number: 4,746,509 Haggiage et al. 45 Date of Patent: May 24, 1988 4,555,524 11/1985 Gruber et al. ...................... 514/947 (54) TRANSDERMAL MEDICAMENT 4,695,464 9/1987 Alderman ........................... 424/449 75) Inventors: Johnny Haggiage, Lyons; Christian 4,699,779 10/1987 Palinczar ............................. 514/937 Pusineri, Serezin du Rhone, both of France FOREIGN PATENT DOCUMENTS 2421610 4/1979 France. 73 Assignee: Rhone-Poulenc Sante, Courbevoie, 2093344 9/1982 United Kingdom. France 2095.108 9/1982 United Kingdom. (21) Appl. No.: 14,190 OTHER PUBLICATIONS (22 Filed: Feb. 3, 1987 Rieg-Falson, C.A. 105: 66340d (1986). Jan, C.A. 105: 49085g (1986). Related U.S. Application Data Haggiage, C.A. 102: 137796h (1985). 63 Continuation of Ser. No. 592,817, Mar. 23, 1984, aban Roux, C.A. 85: 198178k (1976). doned. Saito et al, Arzneim. Forsch 33(11)m. 9: 1301-1305 (1983). 30 Foreign Application Priority Data Nitto Electric, C.A. 96: 187302x (1982). Mar. 24, 1983 FR France ................................ 83 04839 CA, 96: 187302x. 51 Int, Cl." ...................... A61L 15/03; A61F 13/00; Primary Examiner-Shep K. Rose A61K9/70 Attorney, Agent, or Firm-Stevens, Davis, Miller & 52 U.S. C. ..................................... 424/449; 514/947 Mosher 58 Field of Search ................ 424/449; 604/896, 897; 514/947 57 ABSTRACT New transdermal medicaments comprise the active (56) References Cited ingredient dispersed in a heat-reversible, non-cross U.S. PATENT DOCUMENTS linked, film-forming, homogeneous polymer optionally 3,262,450 7/1966 Elias ...................................... 424/28 with a non-ionic emulsifier and, if appropriate, a hydro 3,624,224 11/1971 Wei et al............................... 424/28 phobic, water-insoluble copolymer. 3,934,016 1/1976 Roux et al. .. ... 514/871 3,985,892 10/1976 Roux et al. .......................... 514/871 18 Claims, No Drawings 4,746,509 1. 2 a function of the sensitivity of the patient, the skin act TRANSIDERMAL MEDCAMENT ing as a regulatory membrane. It has now been found, and this is the object of the This application is a continuation of application Ser. present invention, that microporous membranes can No. 592,817, filed Mar. 23, 1984 now abandoned. 5 advantageously be replaced by homogeneous mem The present invention relates to transdermal medica branes in which the variable hydrophilicity enables the ments. kinetics of the release of the active ingredient to be More particularly, the invention relates to a new controlled. galenical form of medicaments which may be, for exam The new transdermal form of the present invention ple, an antianginal product (isosorbide dinitrate, isosor 10 differs from known systems by the nature of the constit bide 5-mononitrate and trinitrin), antiemetic product uents and by the possibility of regulation of the kinetics (metopimazine and dimenhydrinate), anticholinergic of the release of the active ingredient by a process product (scopolamine), non-steroid anti-inflammatory which does not use a microporous membrane. product (ketoprofen), steroid anti-inflammatory prod In the new transdermal medicament, the active ingre 15 dient is dispersed in crystalline form and/or, preferably, uct (prednisolone and dexamethasone), antihyperten in a solubilised form in a homogeneous elastomeric sive product (clonidine), beta-blocking product matrix with, if necessary, a non-ionic emulsifying agent. (acebutolol), vasodilator product (nicergoline), neuro By varying the hydrophilic character of the mixture, it leptic product (phenothiazines), tranquilliser product is possible to determine and to control the rate of release (benzodiazepines, suriclone and suproclone), broncho 20 of the active ingredient. dilator product (phenylpropanolamine), antispasmodic It is furthermore possible to add to the mixture ran product (butylhyoscine bromide), or hormone (estra dom or graft copolymers of which one of the sequences diol). or one of the grafts is incompatible with the matrix and These medicaments, which are active at relatively has a low surface energy (less than or equal to 30 erg low doses, require progressive release in the organism 25 cm2). These sequences or grafts lead to a concentration to be of maximum effectiveness. In general, these medi of copolymer at the surface, forming a homogeneous caments are used in the form of pressed tablets, tablets membrane which permits complementary control of the which can be administered perorally or sublingually or release, favouring the achievement of zero order kinet suppositories. When used in this form, the medicaments ics of release. These compounds may be, for example, have a relatively short duration of action which, for 30 random or graft copolymers based on polydimethylsi some of them, can be less than 1 hour. Continuous treat loxane. ment requires the product to be taken at well-defined To provide the transdermal medicament of the inven intervals of time, but without a regular action being tion, it is particularly advantageous to use heat-reversi obtained. It is particularly important to have available ble, non-crosslinked, film-forming polymers which are galenical forms which ensure continuous and controlled 35 insoluble in water but may be water-miscible and in release of the active principle in the organism to pro which it is possible to vary the hydrophilic character. vide as constant an effect as possible over a defined The films obtained from these polymers swell in the period, which can reach several hours or even several presence of water (in the form of liquid or vapour) and days. the degree of swelling can be adjusted by the hydro For this purpose, compositions which act by percu philic lipophilic balance of the matrix, the additive and taneous absorption and in which the dose administered the active ingredient. can be easily controlled and which release the active More particularly, polyurethane/polyoxyethylene principle in the organism in a regular manner have been glycol (POEG)/poloxypropylene glycol (POPG) co proposed. Such galenical forms facilitate the adminis polymers are suitable for this purpose. It may be advan tration of the active principle. They permit direct access 45 tageous to use polyurethanes based on a polyether or to the systemic circulation without passage through the polyester, such as polytetramethylene glycols, polyca gastrointestinal tract, and they avoid the first-path ef prolactones or polyadipates, for example the products fect. marketed under the names Pellethane, Estane or Quinn. Various systems have been proposed for providing Other heat-reversible elastomers can also be used, such transdermal compositions. For example, according to 50 as polyamides, polyesters, polyethers or polyolefines. U.S. Pat. No. 3,797,494, regulation of the release is In general, the hydrophilic (or hydrophobic) charac ensured by a microporous membrane. The system con ter of a copolymer may be determined by the degree of sists of a reservoir component containing the active swelling in a humid atmosphere in the following man ingredient, a microporous membrane, and an adhesive ner: A sample, which has first been weighed, is placed for attaching the system on the skin. 55 in a saturated humid atmosphere for at least one night at A system which does not contain a microporous a temperature of about 20° C. The weight of the swollen membrane, the skin of the patient acting as the flow sample enables the degree of hydration to be calculated, regulating membrane, can also be used, as described, for this being directly related to the hydrophilicity of the example, in European patent application No. 13,606. polymer. For example, in the case of polyurethane/- The active principle is contained in a system based on 60 POEG POPG copolymers, the hydrophilic character is polyvinyl alcohol and a water-soluble gel based on a function of the POEG/POPG ratio. In this case, the polyvinylpyrrolidone. copolymer is hydrophilic if the POEG/POPG ratio is Other preparations have been described, in which greater than 1:1, and it is hydrophobic if the POEG/- latices of silicones or of elastomeric polymers are used, POPG ratio is less than 1, the hydrophilic or hydropho for example, in French Pat. No. 2,497,457 or U.S. Pat. 65 bic character being more or less pronounced, depending No. 4,336,243. on the exact value of the ratio. These various systems may present technological Dispersion of the active principle in the polymer difficulties of implementation or give results which are matrix is ensured by means of non-ionic emulsifiers 4,746,509 3 4 which are compatible with the polymer matrix and with non-ionic emulsifier (Plurol stéarique) and 10% by the active principle, these emulsifiers generally being weight of isosorbide dinitrate are prepared and the those used in cosmetology and in pharmacy as ingredi amount of released active product which accumulates is ents for creams, milks or ointments or as gelling or measured as a function of time. dispersing agents, or as excipients for suppositories. 5 The results are summarised in Table I. These non-ionic emulsifiers based on glycol polymers or glycerol polymers are in general polycondensates of TABLE I ethylene oxide with fatty acids or fatty alcohols, sorbi Polyurethane/POEG/POPG tan esters, triglycerides with free hydroxyl groups, R st POEG kr Delay time polypropylene glycol monoglycerides or polyglycerol 10 POPG mg/cm. h. t1 (hours) esters. Non-ionic emulsifiers of this type which can be 75/25 1.06 O used include, in particular, products manufactured and 50/50 0.6 0.3 marketed, for example, by Société Gattefosse, such as 25/75 0.5 0.77 Plurol stéarique (polyglycerol palmitostearate), Plurol isostéarique (polyglycerol isostearate), Sucroester WE 15 These results show that the rate of release is higher 15 (sucrose monopalmitate), Labrafil CS2735 (polyoxy for a hydrophilic polymer (POEG/POPG=75/25) ethylene oleyl glyceride), Transcutol (diethylene glycol than for a hydrophobic polymer (POEG/- monoethyl ether) or Labrasol (polyoxyethylene POPG=25/75). C8-C10-glycerides).
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