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|||||||||| US005538737A United States Patent (19) 11) Patent Number: 5,538.737 Leonard et al. 45 Date of Patent: Jul. 23, 1996 54) ORAL COMPOSITIONS OF 5,348,748 9/1994 Sheth et al. ............................. 424/494 HANTAGONISTS 5,360,615 11/1994 Yu et al. ................................. 424/455 FOREIGN PATENT DOCUMENTS 75 Inventors: Thomas W. Leonard; David P. Hause: Frederick D. Sancilio, all of 1565966 4/1980 United Kingdom. Wilmington; James Swarbrick, 2222772 3/1990 United Kingdom. Hampstead; Edward S. Wilson, WO94/O856O 4f1991 WPO : Wilmington, all of N.C. WO94/O8576 4/1994 WIPO : OTHER PUBLICATIONS (73) Assignee: Applied Analytical Industries, Inc., Wilmington, N.C. R. Teraoka et al., Effects of Temperatures and Relative Humidity on the Solid State Chemical Stability of Raniti (21 Appl. No.: 347,586 dine Hydrochloride American Pharmaceutical Association 82(6) pp. 601-604 (1993). 22 Filed: Nov.30, 1994 Chem. Abstracts 114:12.9112q Ranitidine capsules (1990). Madan, et al., Preparation and Characterization of Raniti I51) Int. Cl. .............................................. A61K 9/48 dine-HCl Crystals Drug Development and Industrial Phar 52 U.S. Cl. .......................... 424/451; 424/455; 424/456; macy 2009): 1571 (1994). 514/938; 514/943 Teraoka, et al., Effects of Temperature and Relative Humid 58 Field of Search ..................................... 424/451, 455, ity on the Solid-State Chemical Stability of Ranitidine 424/456; 514/937 Hydrochloride Journal of Pharmaceutical Sciences 82(6):601 (1993). (56) References Cited P. P. Constantinides, et al., Formulation and Intestinal U.S. PATENT DOCUMENTS Absorption Enhancement Evaluation of Water-in –Oil Microemulsions Incorporating Medium-Chain Glycerides, 3,376,199 4/1968 James et al. .............................. 67/83 Pharmaceutical Research 11 No. 10, pp. 1385–1390 (1994). 4,128,658 12/1978 Price et al. ... ... 424/285 Notification of Transmittal of the International Search 4,169,855 10/1979 Price et al............................... 260,583 4,279,819 7/1981 Price et al. 260/326.5 Report or the Declaration; PCT/US95/15256. 4,521,431 6/1985 Crookes ........ ... 514/47 Primary Examiner-Thurman K. Page 4,585,790 4/1986 Padfield et al. ... ... 514,471 Assistant Examiner James M. Spear 4,672,133 6/1987 Crookes ....... ... 549,495 4,711,782 12/1987 Okada et al ... 424/455 Attorney, Agent, or Firm-Bell, Seltzer, Park & Gibson 4,880,636 11/1989 Franz ........ ... 424/480 57 ABSTRACT 5,007,790 4/1991. Shell ......... ... 424/45 5,028,432 7/1991 Chopra et al. ... ... 414.f451 The present invention provides pharmaceutical capsule 5,032,393 7/1991 Douglas et al. .......................... 424f79 compositions for the oral administration of an H-antago 5,068,249 11/1991 Long ............ ... 514.f471 nist. The composition includes a capsule containing an 5,102,665 4/1992 Schaeffer . ... 424/466 emulsion having a water portion and an oil portion. A 5,169,855 10/1979 Price et al. ... ... 260,583 pharmaceutically acceptable salt of an H-antagonist is 5,169,864 12/1992 Johnson et al. .. 514,471 5,175,147, 12/1992 Folkman et al. 514f12 dissolved in the water portion. The composition delivers a 5,206,219 4/1993 Desai .......................................... 51413 therapeutically effective amount of the H-antagonist to a 5,229,137 7/1993 Wolfe ............... ... 424,687 patient in need thereof. The present invention also provides 5,271,945 12/1993 Yoshioka et al. ... 424/489 methods of making the capsule composition. 5,304,571 4/994 Johnson et al. ...... ... 514/471 5.330,767 7/1994 Yamamoto et al. .................... 424/497 47 Claims, No Drawings 5,538.737 1. 2 ORAL COMPOSITIONS OF pharmaceutically acceptable salt of the pharmaceutically HANTAGONISTS active agent is dissolved in the water portion. The water-in oil emulsion is compatible with the capsule into which it is FIELD OF THE INVENTION filled. The composition delivers a therapeutically effective amount of the agent to a patient in need thereof. This invention relates to oral delivery systems for phar maceutically active agents and more particularly to new oral Advantageously, the product is not subject to the vagaries pharmaceutical delivery products for H-antagonist agents. of polymorphism, because the pharmaceutically active agent is in solution. The pharmaceutically active agent being in BACKGROUND OF THE INVENTION 10 solution allows for more rapid delivery of the compound, and obviates concerns about polymorphic instability and The H-antagonist agents (hereinafter "H-antagonists") transformation. The salt of the pharmaceutically active agent are routinely administered orally to patients suffering from is sufficiently soluble in the aqueous medium to avoid the gastrointestinal conditions such as ulcers, dyspepsia, various formation of crystals of the pharmaceutically active agent. reflux indications and the like. Typically, the H-antagonist 15 As a second advantage, the composition of the present is delivered to the patient in tablet or powder-filled capsule invention provides a liquid composition (i.e., an emulsion) form. Other liquid oral compositions such as syrups have of the pharmaceutically active agent for oral administration also been proposed (see, U.S. Pat. No. 4,128,658 to Price et while overcoming the unpalatably bitter taste of previously al.) known liquid formulations. In addition, the liquid emulsion The H-antagonists are known to have an unpalatably 20 is advantageously compatible with the capsule walls. It is bitter taste when ingested in any form other than solid known in the art that aqueous solutions, e.g., water, and capsule or tablet form. Additionally, capsules or tablets, many hydrolytic Solvents attack starch or gelatin capsules. which contain the drug in solid crystalline form, may exhibit However, the compositions of the present invention provide non-uniform absorption characteristics because of multiple a liquid water-in-oil emulsion which does not degrade the polymorphic forms. Some H-antagonists exhibit multiple 25 walls of starch or gelatin capsules. polymorphic forms, and absorption characteristics can vary As a second aspect, the present invention provides a between these forms. In addition, polymorphic forms may method of forming an emulsion containing an H-antago not be stable, and may undergo transformation in the solid nist. The method includes (a) dissolving a pharmaceutically dosage forms. Alternative formulations targeted at resolving acceptable Salt of an H2-antagonist in an aqueous medium to these disadvantages have been proposed. For example, PCT 30 form a water portion, (b) combining the water portion with WO94/08560 and U.S. Pat. No. 5,068,249 to Schaeffer an oil portion including an edible oil and an emulsifying propose chewable or effervescent tablets. U.S. Pat. No. agent to form a water portion and oil portion matrix, and (c) 5,008,256 to Long proposes formation of complexes of emulsifying the matrix to form the emulsion. H-antagonists. U.S. Pat. No. 5,032,393 to Douglas et al. As a third aspect, the present invention provides an proposes resin adsorption. PCT WO94/08576, and U.S. Pat. 35 alternate method of forming an emulsion containing an Nos. 5,028,432 to Chopra et al. and 5,007,790 to Shell H-antagonist. The method includes (a) dissolving a free propose non-aqueous formations of H2-antagonists in fats or base of an H2-antagonist in an inorganic acid medium to oils. U.S. Pat. No. 5.229,137 to Wolfe proposes solid or form a water portion, (b) combining the water portion with liquid formulations which include an H-antagonist in com an oil portion including an edible oil and an emulsifying bination with an antacid. 40 One H-antagonist, ranitidine, also has been reported to agent to form a water portion and oil portion matrix, and (c) be incorporated into a non-aqueous composition comprised emulsifying the matrix to form the emulsion. of a solid wax or oil such as "Miglyol' and a surfactant such As a fourth aspect, the present invention provides a as lecithin, and then filled into a gelatin capsule. See, C.A. method of making a pharmaceutical capsule composition for 114(14) 129112. U.S. Pat. No. 4,585,790 to Padfield et al. 45 the oral administration of a therapeutically effective amount proposes oral and injectable aqueous compositions of ran of a pharmaceutically active agent, e.g., an H-antagonist. The method includes (a) dissolving a pharmaceutically itidine having a pH range from 6.5 to 7.5. However these acceptable Salt of the H-antagonist in an aqueous medium, solutions are known to exhibit stability problems for inject (b) combining the water portion with an oil portion includ able administration or when the solids are exposed to ing an edible oil and an emulsifying agent, to form a water hygroscopic conditions. See, R. Tenaoka et al. J. Pharm. Sci. 50 portion and oil portion matrix, (c) emulsifying the matrix to 82, 601 (1993). form the emulsion, and (d) filling the capsule with the Other methods of administering various pharmaceuticals, emulsion. The edible oil of the oil portion of the emulsion is including other anti-ulcer drugs have been proposed. For compatible with the capsule, such that the emulsion does not example, U.S. Pat. No. 4,711,782 to Okada et al. proposes degrade the capsule wall. a microcapsule containing a drug and a drug retaining 55 substance, which is formed by preparing a water-in-oil As a fifth aspect, the present invention provides an emulsion, thickening or solidifying the aqueous layer, and alternate method of making
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