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Ibuprofen Composition

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Ibuprofen Composition Europaisches Patentamt (19) European Patent Office Office europeeneen des brevets ^ £ P 0 945 1 32 A2 (12) EUROPEAN PATENT APPLICATION (43) Date of publication: (51) intci.6: A61K31/19, A61K9/00, 29.09.1999 Bulletin 1999/39 A61K47/12 (21) Application number: 99300004.1 (22) Date of filing: 04.01.1999 (84) Designated Contracting States: (72) Inventors: AT BE CH CY DE DK ES Fl FR GB GR IE IT LI LU • Bunick, Frank J. MC NL PT SE Randolph, NJ 07896 (US) Designated Extension States: • Lin, Feng ALLTLVMKROSI Horsham, PA 19044 (US) (30) Priority: 02.01.1998 US 2447 (74) Representative: Mercer, Christopher Paul et al Carpmaels & Ransford (71) Applicant: McNEIL-PPC, INC. 43, Bloomsbury Square Skillman, NJ 08558-9418 (US) London WC1 A 2RA (GB) (54) Ibuprofen composition (57) Fumaric acid is added in amounts sufficient to reduce the burn after taste commonly associated with propionic acid derivatives. CM < CM CO lO ^> O) o a. LU Printed by Jouve, 75001 PARIS (FR) 1 EP 0 945 132 A2 2 Description DETAILED DESCRIPTION OF THE INVENTION BACKGROUND OF THE INVENTION [0009] Propionic acid derivatives are a well known class of analgesic compounds. As used herein propionic [0001] The present invention relates to ibuprofen s acid derivatives are understood to include, but are not compositions, more specifically to an ibuprofen compo- limited to, ibuprofen, naproxen benoxaprofen, naproxen sitions with reduced burn characteristics. sodium, flurbiprofen, fenoprofen, fenbuprofen, ketopro- [0002] Many flavors and sweeteners have been add- fen indoprofen, pirprofen, carpofen, oxaprofen, prano- ed to medication in order to make them more palatable profen, microprofen, tioxaprofen, suproprofen, almino- and to mask the burn and after taste which is common 10 profen, tiaprofenic acid, fluprofen and bucloxic acid. The with many medications. Despite numerous efforts to find structural formula is set forth in US Patent 4,923,898, an effective means to eliminate this burn, there is a con- hereby incorporated by reference. Propionic acid deriv- tinuing need for a method to effectively eliminate the atives as defined herein are defined as pharmaceutical- burning sensation with mediations, preferably the burn ly acceptable analgesics/non-steroidal anti-inflammato- can be reduced to a level such that a chewable compo- 15 ry drugs having a free -CH(CH3)COOH or sition can be provided. -CH2CH2COOH or a pharmaceutical^ acceptable salt [0003] Ibuprofen is a well known medication which group, such as -CH(CH3)COO-Na+ or CH2CH2COO- possesses an unpalatable burning feeling in the mouth Na+, which are typically attached directly or via a carb- and throat after ingestion. onyl functionality to an aromatic ring system. [0004] Japanese Patent Application 9 (1997)-2949 20 [0010] The acetic acid derivatives for use herein in- assigned to American Home Products attempts to elim- clude, but are not limited to, indomethacin, sulindac, tol- inate the unpalatable aftertaste by providing only one metin, diclofenac, fenclofenac, alsoclofenac, ibufenac, enantiomer. The patent application discloses the sepa- isoxepac, furofenac, tiopinac, zidometacin, acemi- ration of ibuprofen from its racemic mixture to form an netacin, fentiazac, clidanac, and oxepinac. Structurally orally administered drug composition which contains 25 related acetic acid derivatives having similar analgesic only the S(+)-ibuprofen and essentially no R(-)-ibupro- and anti-inflammatory properties included within the fen. While this approach may provide a more palatable scope of the invention include, tolmetin, sulindac, in- form of ibuprofen the separation and isolation of the domethacin, diclofenac, alclofenac, fenclozic acid and enantiomers are difficult. ibufenac. [0005] US Patent 4,762,702 discloses ibuprofen par- 30 [0011] Propionic acid derivatives are typically admin- tides enveloped by a coating of hydro-colloid and fu- istered on a daily ranging from about 50 to about 2000 maric acid. The preferred hydro-colloid composition milligrams, preferably from about 1 00 to 1 600 and most comprises xantham gum and/or maltodextrin. The re- preferably from about 200 to about 1 200 milligrams. sulting product is an effeverfescent mixture which is vac- [0012] Ibuprofen is a widely used, well known non- uum dried. The patent discloses this method as over- 35 steroidal anti-inflammatory known propionic acid deriv- coming the shortcoming of prior art preparations due to ative. Ibuprofen is chemically known as 2-(4-isobutyl- the envelopment of the ibuprofen crystals by the hydro- phenyl)propionic acid. As used herein ibuprofen is un- colloid in the presence of the fumaric acid. derstood to include 2-(4-isobutylphenyl)-propionic acid [0006] Despite the disclosure of the above patent and as well as the pharmaceutical^ acceptable salts. Suit- application, a simpler and less costly method is provid- 40 able ibuprofen salts include arginine, lysine, hystadine, ing atastemasked ibuprofen composition. as well as other salts described in US Patent No. 4,279,926, 4,873,231, 5,424,075,5,510,385 the con- SUMMARY OF THE INVENTION tents of which are incorporated by reference. [0013] Fumaric acid is a widely available pharmaceu- [0007] The present invention provides propionic acid 45 tical^ acceptable acid. The concentration of fumaric ac- derivatives with fumaric acid in an amount from about id present to inhibit the burn of propionic acid derivative 50 to about 150 percent of the amount of the propionic will vary on the amount of burn reduction desired. Gen- acid derivative. The present invention provides fumaric erally the level of fumaric acid is from about 50 to about acid sufficient to reduce the burn after-taste of propionic 150 weight percent of the propionic acid derivative dos- acid in the absence of a hydro-colloid agent. In a pre- so50 age. Typically the level of fumaric acid is from about 60 ferred embodiment the propionic acid derivative-f umaric to about 100 percent by weight of the level of propionic composition is provided in a chewable form. acid derivative and most preferably from about 70 to [0008] A method for inhibiting the burn after-taste of about 90 percent by weight of the level of propionic acid propionic acid derivatives by providing an effective derivative dosage. amount of fumaric acid is also provided by the present 55 [0014] Contrary to the teaching of prior disclosures, invention. the present invention does not require the incorporation of a hydrocolloid material in order to be effective. The present invention may be incorporated in the following 2 3 EP 0 945 132 A2 4 embodiments. clude boric acid, sodium benzoate, sodium acetate, so- [001 5] The simplest and preferred embodiment is the dium chloride, leucine, polyethylene glycol and the like. incorporation of fumaric acid in a matrix, i.e., freely and Typical disintegrates include, starch derived from wood, randomly provided in a mixture. In this embodiment, the maize, potato, and rice, methylcellulose, magnesium sil- propionic acid derivative, preferably ibuprofen, and fu- 5 icates, aluminum silicates, sucrose, dextrose, malodex- maric acid are provided in a matrix within the caplet, tab- trose, agar, benoite, alginic acid, wood products, guar let or capsule form. gum, citric pulp, sodium lauryl sulfate and the like. [0016] In another embodiment of the invention the [0022] The present invention may be provided in liq- ibuprofen and fumaric acid are provided in a granulation. uid form, e.g. an elixir, suspension, or syrup. The liquid Typically this involves the admixing of the propionic acid 10 formulations are prepared using manufacturing meth- derivative, fumaric acid as well as sugars, binders, water ods and pharmaceutical^ acceptable surfactants, dis- and other ingredients together using equipment well persants and diluents known in the art. Preferably the known in the art. present invention is provided in caplets, capsules, tab- [0017] For example, US Pat. Number 5,429,825 dis- lets and most preferably in a chewable form. closes rotomelt granulation methods, the contents here- is [0023] As used throughout this specification burn is by incorporated by reference as set forth here in its en- understood to mean the aftertaste, commonly identified tirety. The mixture is then dried and milled. The milled as metallic, noted when taking ibuprofen. This aftertaste product is then in suitable form to be compressed into is different than bitterness inasmuch as the addition of a tablet. Preferably disentgrants are added to the ad- a sweetener is not effective in reducing the aftertaste. mixture to aid the release of the active ingredients to the 20 [0024] Alternatively the ibuprofen, fumaric acid com- user. In a highly preferred embodiment the propionic ac- position may be added at appropriate levels to beverag- id, fumaric acid is provided such that a chewable tablet es, food and other edible compositions which may be is available to those who have difficulty in swallowing a desired. It is also anticipated that the ibuprofen/fumaric tablet. acid compositions of the present invention may also be [0018] In another embodiment of the present inven- 25 employed in veterinarian applications. tion the fumaric acid/propionic acid is provided in the [0025] Without wishing to be bound by any theory the presence of a non-hydrocolloid binder. Preferably the incorporation of fumaric acid to the propionic acid deriv- non-hydrocolloid binder is a pharmaceutical^ accepta- ative reduces the characteristic after taste burn by acid- ble wax or fat. Suitable waxes and fats include, glyceryl ifying the saliva sufficiently to maintain the protonated monosterate, hydrogenated tallow, myristyl alcohol, 30 form of the propionic acid derivative. The protonated myristic acid, stearyl alcohol, substituted monoglycer- form of the propionic acid derivative has low solubility ides, substituted diglycerides, substituted triglycerides, and hence has low irritation to the throat mucosa. Unlike beeswax, carnuaba wax, japan wax acetylate other acidulates, fumaric acid dissolves slowly such that monoglycerides and the like. Combinations of two or its sour taste is minimal in the mouth but sufficient to more of the non-colloid binders may be used.
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