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Use of Tenidap to Inhibit Activation of Collagenase and to Inhibit the Activity of Myeloperoxidase

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Use of Tenidap to Inhibit Activation of Collagenase and to Inhibit the Activity of Myeloperoxidase Europaisches Patentamt 19) J) European Patent Office Office europeen des brevets (n) Publication number : 0 448 253 A2 EUROPEAN PATENT APPLICATION @ Application number : 91301890.9 © mt. ci.5: A61K 31/405 @ Date of filing : 07.03.91 (§) Priority : 19.03.90 US 495868 (72) Inventor : Blackburn, Warren Darrel Jr. 312 Ridge Road Birmingham, Alabama (US) (43) Date of publication of application : Inventor: Loose, Lei and David 25.09.91 Bulletin 91/39 165 Rockwell Street Norwich, Connecticut (US) (84) Designated Contracting States : AT BE CH DE DK FR GB IT LI LU NL SE (74) Representative : Wood, David John et al PFIZER LIMITED, Ramsgate Road Sandwich, Kent CT13 9NJ (GB) @ Applicant : PFIZER INC. 235 East 42nd Street New York, N.Y. 10017 (US) (54) Use of tenidap to inhibit activation of collagenase and to inhibit the activity of myeloperoxidase. (57) This invention relates to the use of tenidap, 5-chloro-2,3-dihydro-2-oxo-3-(2-thienylcarbonyl)-indole- 1-carboxamide, for the manufacture of a composition for inhibiting the activation of collagenase in a mammal and for inhibiting the activity of myeloperoxidase in a mammal. This invention also relates to the use of tenidap and its salts for the manufacture of a medicament for treating collagenase mediated disorders and diseases such as bone resorption disorders, corneal ulceration, periodontal disease, inflammatory disease and wounds of the skin and bums in mammals. CO in CM 00 Q_ UJ Jouve, 18, rue Saint-Denis, 75001 PARIS EP 0 448 253 A2 JSE OF TENIDAP TO INHIBIT ACTIVATION OF COLLAGENASE AND TO INHIBIT THE ACTIVITY OF MYELOPEROXIDASE This invention relates to the use of tenidap and the pharmaceutically-acceptable base salts thereof to inhibit activation of collagenase in a mammal. This invention also relates to the use of tenidap and the pharmaceuti- cally-acceptable base salts thereof for treating collagenase mediated disorders and diseases such as bone resorption disorders, corneal ulceration, periodontal disease, inflammatory diseases and wounds of the skin > and burns in a mammal. Further, this invention relates to the use of tenidap and the pharmaceutically-accept- able base salts thereof to inhibit the activity of myeloperoxidase in a mammal. The methods of this invention comprise administering an effective amount of tenidap or salts thereof to such a mammal. Tenidap, 5-chloro-2,3-dihydro-2-oxo-3-(2-thienyl-carbonyl)-indole-1-carboxamide, has the structural for- mula (5 20 Tenidap and the pharmaceutically-acceptable base salts thereof, among other 3-substituted-2-oxindole-1-car- boxamides, are disclosed and claimed in U.S. 4,556,672 which is assigned to the assignee hereof. That patent discloses that those compounds, in addition to being useful as antiinflammatory and analgesic agents, are 25 inhibitors of both the cyclooxygenase (CO) and lipoxygenase (LO) enzymes. The teachings thereof are incor- porated herein by reference. The use of tenidap and its pharmaceutically-accceptable base salts, among certain other 3-substituted-2- oxindole-1-carboxamides, to inhibit interleukin-1 biosynthesis in a mammal and to treat interleukin-1 mediated disorders and dysfunctions is disclosed in U.S. 4,861,794 which is assigned to the assignee hereof. 30 U.S. 4,853,409, assigned to the assignee hereof, discloses -the use of tenidap and its pharmaceutically- acceptable base salts, among certain other 3-substituted-2-oxindole-1-carboxamides, to suppress T-cell func- tion in a mammal and to treat T-cell mediated autoimmune disorders of the systemic or organ specific type. An anhydrous, crystalline form of the sodium salt of tenidap is disclosed in European Patent Application 277,738 which has been filed in the name of the assignee hereof. 35 Collagenase is a protease which is stored within neutrophil specific granules in a latent form. (Hasty, K.A., et al., J. Biol. Chem. 261:5645-5650 (1986) and Hasty, K.A., et al., J. Biol. Chem. 262:10048-10052 (1987).] Collagenase, in its activated form, mediates a variety of disorders and diseases in a mammal. These disorders and diseases include, but are not limited to, bone resorption disorders such as osteoporosis and metastatic bone cancer, corneal ulceration, periodontal disease, inflammatory joint disease, inflammatory diseases and 40 wounds of the skin and burns. (Harris, E.D., et al., NEJM 291:605-609 (1974) and Harris, E.D., et al., NEJM 291:652-660 (1974).] Collagenase can be activated from its latent form by hypochlorous acid. [Weiss, S.J., et al., Science 227:747-749 (1 985).] The enzyme myeloperoxidase converts hydrogen peroxide, itself the dismut- ased product of superoxide radicals, into hypochlorous acid. Once activated, collagenase is capable of irre- versibly cleaving collagen of types 1, 2 and 3. (Hasty, D.A., et al., J. Biol. Chem. 262: 1 0048-1 0052(1 987).] 45 It has been reported that certain gold compounds can interfere with activated collagenase, but only in the presence of organomercurials. (Mallya, S.K., et al., J. Biol. Chem. 264:1594-1601 (1989) and Mallya, S.K. et al., Biochem. Biophys. Res. Comm. 144:101-108 (1987).] Further, penicillamine has been reported to scavenge hypochlorite and inhibit its formation by, myeloperoxidase. (Cuperus, R.A., et al., Arthritis Rheum. 28:1228- 1233 (1985).] 50 However, until the invention herein, there was no report of use or intent to use tenidap or the salts thereof to inhibit the activation of collagenase and to treat collagenase mediated disorders and diseases such as bone resorption disorders, corneal ulceration, periodontal disease, inflammatory diseases of the skin and burns with tenidap nor any appreciation of its role in such treatments. Further, there was no report of use or intent to use tenidap or the salts thereof to inhibit the activity of myeloperoxidase with tenidap nor any appreciation of its 2 EP 0 448 253 A2 ability to inhibit myeloperoxidase in a mammal. It has been found that tenidap and the pharmaceutically-acceptable base salts thereof inhibit the activation of collagenase in a mammal and thus are useful in inhibiting the activation of collagenase perse and in treating collagenase mediated disorders and diseases. Such collagenase mediated disorders and diseases include, 5 but are not limited to, bone resorption disorders, corneal ulceration, periodontal disease, inflammatory diseases and wounds of the skin and bums. Further, it has been found that-tenidap and its pharmaceutically-acceptable base salts inhibit the activity of myeloperoxidase in a mammal and are useful in inhibiting myeloperoxidase per se. The method of using tenidap and its pharmaceutically-acceptable base salts comprises administering to 10 a mammal an effective amount thereof. Administration can comprise any known method for therapeutically pro- viding a compound to a mammal such as by oral or parenteral administration as defined hereinbelow. Tenidap, which has the chemical structure 15 r 20 25 its pharmaceutically-acceptable base salts and the preparation thereof are described in U.S. 4,556,672, the teaching of which are incorporated herein by reference. This invention concerns new uses for tenidap and its salts which comprise inhibiting the activation of collagenase in a mammal and inhibiting the activity of myeloperoxidase in a mammal. Also within the scope of this invention are methods of treating collagenase mediated disorders and diseases in a mammal. Such collagenase mediated disorders and diseases include, 30 but are not limited to, bone resorption disorders such as osteoporosis and metastatic bone cancer, corneal ulceration, periodontal disease, inflammatory diseases and wounds of the skin and burns. As disclosed in U.S. 4,556,672, tenidap is acidic and forms base salts. All such base salts are within the scope of this invention and can be formed as taught by that patent. Such suitable salts, within the scope of this invention, include both the organic and inorganic types and include, but are not limited to, the salts formed with 35 ammonia, organic amines, alkali metal hydroxides, alkali metal carbonates, alkali metal bicarbonates, alkali metal hydrides, alkali metal alkoxides, alkaline earth metal hydroxides, alkaline earth metal carbonates, alkaline earth metal hydrides and alkaline earth metal alkoxides. Representative examples of bases which form such base salts include ammonia, primary amines, such as n-propylamine, n-butylamine, aniline, cyclohexylamine, benzylamine, p-toluidine, ethanolamine and glucamine; secondary amines, such as diethylamine, dieth- 40 anolamine, N-methylglucamine, N-methylaniline, morpholine, pyrrolidine and piperidine; tertiary amines, such astriethylamine, triethanolamine, N,N-dimethylaniline, N-ethylpiperidine and N-methylmorpholine; hydroxides, such as sodium hydroxide; alkoxides such as sodium ethoxide and potassium methoxide; hydrides such as calcium hydride and sodium hydride; and carbonates such as potassium carbonate and sodium carbonate. Pre- ferred salts are those of sodium, potassium, ammonium, ethanolamine, diethanolamine and triethanolamine. 45 Particularly preferred are the sodium salts. An anhydrous crystalline form of such a sodium salt is disclosed in European Patent Application 277,738, filed in the name of the assignee hereof. The teachings, thereof which are incorporated herein by reference. Also within the scope of this invention are the solvates such as the hemihydrates and monohydrates of the compounds hereinabove described. so The methods of this invention comprise administering tenidap and the pharmaceutically-acceptable base salts thereof
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