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United States Patent (19) (11) 4,378,354 Ghyczy Et Al

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United States Patent (19) (11) 4,378,354 Ghyczy Et Al United States Patent (19) (11) 4,378,354 Ghyczy et al. 45 Mar. 29, 1983 54) NFLAMMATON-PREVENTING 51 Int. Clº. A61K 31/685 PHARMACEUTICAL COMPOSITION OF (52] U.S. Cl. .… 424/199 ORAL ADMINISTRATION 58) Field of Search......................................... 424/199 75) Inventors: Miklos Ghyczy; Adorjan Erdös, both of Cologne; Ginter Heidemann, Primary Examiner-Stanley J. Friedman Geilenkirchen-Tripsrath; Götz Attorney, Agent, or Firm-Burns, Doane, Swecker & Ritzmann, Cologne, all of Fed. Rep. Mathis of Germany 57 ABSTRACT 73) Assignee: A. Nattermann & Cie. GmbH, Cologne, Fed. Rep. of Germany A novel pharmaceutical composition is provided which is suitable for the prevention of inflammation and which (21) Appl. No.: 266,217 comprises non-steroidal inflammation-preventing com 22) Filed: May 22, 1981 pound (e.g. pyrazolones, salicylic acid derivatives, in doles, indanes, and phenylacetic acid and anthranilic Related U.S. Application Data acid derivatives) and at least one phospholipid. 62) Division of Ser. No. 104,449, Dec. 14, 1979, Pat. No. 4,332,795. 17 Claims, No Drawings 4,378,354 2 tic substances can be prevented if these substances are INFLAMMATION-PREVENTING combined in a suitable manner with phospholipids. The PHARMACEUTICAL COMPOSITION OF ORAL medicinal compositions of the present invention will ADMINISTRATION therefore contain these antiphologistic substances in conjunction with phospholipids. The phospholipids This is a division of application Ser. NO. 104,449 filed have the advantage over the previously described sub Dec. 17, 1979 now U.S. Pat. No. 4,332,795. stances in that they are body-inherent, can be readily broken down within the body, do not promote any side BACKGROUND OF THE PRESENT INVENTION effects (even if administered continuously (see J. Weih A great number of substances for the effective treat 10 rauch, U.S. Dept. of Agriculture, quoted in National ment of inflammatory illnesses, for example rheuma Enquirer of June 6, 1978, page 33)) and do not possess tism, have been known for a long time. Since the inflam any analgetic or antiphlogistic effect of their own. The mations are often chronic, the treatment with such in admixture of phospholipids with non-steroidal antiphlo flammation-preventing active substances will usually gistic substances substantially lowers the degree of side extend over a long period of time. The non-steroidal 15 effects while the analgetic and antiphlogistic properties antiphlogistic substances used for such continuous treat remain intact. ments very often have undesirable side effects on the digestive tract, such as, for example, in the form of DETAILED DESCRIPTION OF THE PRESENT gastro-intestinal bleeding and stomach ulcers as de INVENTION scribed by Y. H. Lee et al in "Archint. Pharmacodyn.” 20 Natural as well as synthetic phospholipids can be 191, 370-377 (1971) and by K. D. Rainsford in "Agents used in the preparations of the present invention. Natu and Actions' 1977 7(5/6), 573-77, as well as by A. R. ral phospholipids (of plant or animal origin) such as Cooke in "Drugs' 1976, vol. 11, pages 36 to 44. phosphatidylcholine, phosphatidylethanolamine, phos Many attempts have been made to moderate the side phatidylinositol, phosphatidylserine, sphingomyeline, effects of these effective non-steroidal antiphlogistic 25 substances by the admixture of an additional active cephaline, lysolecithin, phosphatidyiglycol, cardiolipin, substance. All mixtures of this type have the disadvan and plasmalogens (which can all be obtained, for exam tage that the additional substance might cause an ulcer. ple, from the soya bean or egg) and mixtures of these on its own, or might even influence adversely the effec phospholipids are suitable for use in the present inven tiveness of the primary non-steriodal antiphlogistic sub 30 tion. Commercially available phosphatidylcholines or StanCe. phosphatidylcholine-mixtures include Phospholipon (R) Attempts have been made, for example, to admix 100, Phospholipon (R) 10OH, Phospholipon (R) 80 and anticholinergic substances or pepsin inhibitors with the Phospholipon (R) 45. Usable synthetic phosphatides in antiphlogistic substances (Y. H. Lee et al., “Archint.- clude, for example, ditetradecanoylphosphatidylcho Pharmacodyn,” 191, 370-377 (1971)). The firm of Rich 35 line, dihexadecanoylphosphatidylcholine, dioleylphos ter Gedeon (DE-OS No. 25 24 902) proposed the ad phatidylcholine or dilinolylphosphatidylcholine and mixture of salicylic acid salts with the antiphlogistic especially dipalmitoylphosphatidylcholine. substances. However, salicylic acid salts have analgetic The following substances are especially suitable non and antiphologistic properties of their own and can steroidal antiphlogistic substances for use in the combi cause strong side effects such as nausea and vomiting as 40 nation proposed by the invention: well as damage of the mucous membrane of the stomach Pyrazolones and especially with the possibility of bleeding if administered over phenylbutazone (4-butyl-1,2-diphenylpyrazolidine-3,5- longer periods of time as reported by E. Mutschler in dion), and “Arzneimittelwirkungen“, wissenschaftliche Verlags oxyphenbutazone (4-butyl-2-(4-hydroxyphenyl)-1-p- geselischaft 1970, pages 76, 77. 45 phhenylpyrazolidine-3,5-dion); The Sumitomo Chemical Co. Ltd. has proposed the Salicylic acid derivatives such as salicylic acid salicylic combination of non-steroidal antiphlogistic substances acid amide, with quinazolines (see DE-OS No. 26.27914) with the acetyl-salicylic acid, purpose of preventing the formation of peptic ulcers benorilate (4-acetamidophenyl-o-acetylsalicylate), and within the area of the digestive tract. However, these 50 diflumisal (5-(2,4-difluorophenyl)-salicylic acid); quinazolines are substances with an analgetic and anti Indoles, especially indometacine and its analogs such as phlogistic effect of their own. U.S. Pat. No. 3,993,767 indometacine (1-(p-chlorobenzyyl)-5-methoxy-2- describes mixtures of non-steroidal antiphlogistic sub , methylindole acetic acid), stances with metaxalon. However, the metaxalon has a glucametacine (-(p-chlorobenzoyl-5-methoxy-2- muscle-relaxing effect. See the Merck Index, Ninth 55 methylindole-3-yl acetic acid glucose amide), edition 1976, page 772. acemetacine (1-(p-chlorobenzoyl)-5-methoxy-3- methylindole-3-acetic acid-glycolic acid-ester), and OBJECTS AND SUMMARY OF THE sulindac (5-fluor-2-methyl-1-p-(methylsulphenyl)-ben INVENTION zylidene-indene-3-acetic acid); It is therefor the object of the present invention to 60 Phenyl acetic acid or phenyl propionic acid derivatives develop an inflammation-preventing medicine which such as will substantially improve the poor compatibility of ibuprofen (2-(4-isobutylphenyl)-propinic acid); non-steroidal antiphlogistic substances without ad naproxen (2-(6-methoxy-2-naphthtyl)-propinic acid), versely influencing the inflammation-preventing effect alclofenac (4-allyloxy-3-chlorophenyl-acetic acid), of these active substances. 65 ketoprofen (2-(3-benzylphenyl)-benzoic acid), It has been found that serious side effects on the di diclofenac (2-(2,6-dichlorophenylamino)-phenyl-acetic gestive tract such as damage to the mucous membrane acid), or gastric ulcer formation by non-steroidal antiphlogis fenoprofen (2-(3-phenyloxyphenyl)-acetic acid), 4,378, 354 3 4. tolmetin (1-methyl-5-(p-toluyl)-pyrrole-2-yl-acetic late, a powder or a suspension. The medicine can fur acid), ther contain the usual quantities of carrier materials flurbiprofen (2-(2-fluorobiphenyl-4-ye-propionic acid), and/or diluents as well as auxiliary substances such as and starch, gelatine, agar, sugar, carboxy-methylcellulose, suprofen (p-2-thenoyl-hydratropic acid) phenylprop polyvinylalcohol, magnesium stearate, sodium alginate rionic acid); and the like. Anthranilic acids and their nitrogen analogs such as The advantageous effectiveness of the novel medi flufenamino acid (N-(m-trifluoromethylphenyl)- cines proposed by the invention is demonstrated by anthranilic acid), several pharmacological tests which are listed below. mefenamino acid (N-(2,3-dimethylphenyl)-anthranilic 10 The development of the ulcer was determined in accor acid), and dance with niflumin acid (2-(3-trifluoromethylaminolino)-nicotinic B. J. R. Whittle, “Brit.J.Pharmakol.' 55, 242-243 acid). (1975), L. Mariani, “Eur.J. Toxicol.Environ.” 8, 335-339 The novel mixture of the present invention compris- 15 (1975), and ing non-steroidal antiphlogistic substances and phos R. Menguy & L. Desbaillets, “Proc.Soc.exp.Bio.” 125, pholipid is particularly suitable for oral application 1108. where the molar ratio of antiphlogistic substance to phospholipid ranges from about 1:0.1 to about 1:20, and Ten male and ten female Wistar-rats (120 to 150 preferably from about 1:0.5 to about 1:2. 20 grams, in weight) which have not fed for 16 hours, were The mixture can be prepared by dissolving the anti used for these tests. The bleeding stomach ulcer was phlogistic substance and the phospholipid in a suitable provoked by oral application of the active substance. organic solvent such as methanol, ethanol or chloro After 3.5 hours, the animals are killed and the stomach form and by subsequently separating the solvent from extracted, opened along the wide curvature and the mixture by distillation. The antiphlogistic substance 25 stretched onto a "Styropor” plate. The mean ulcer can also be dissolved in water at a suitable pH with the factor of the test and of the control group are deter phospholipid being stirred into the solution. The emul mined.
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