Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1996-08-09
1997-09-30
Rotman, Alan L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
546301, 546297, A61K 3144, C07D21372, C07D21336
Patent
active
056726139
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT EP 95/00525 filed Feb. 13, 1995.
The present invention relates to a novel product, 3-2-amino-2-(4-methoxyphenoxy)pyridine, a pharmaceutical composition containing this product, a process for its preparation and its therapeutic use, in particular as an anti-inflammatory active compound to be used topically.
PRIOR ART
Despite the large number of known pharmaceutical active compounds in the therapeutic area associated with inflammatory diseases, research and development of novel products and novel pharmaceutical application forms go on and on. This is in the main because of the fact that the non-steroidal, anti-inflammatory products on oral administration bring with them the problem of side-effects in the gastrointestinal region. If the inflammation is superficial and locally restricted, it is attempted to keep these side-effects as small as possible by the topical administration of the product. Thus e.g. ibuprofen (.alpha.-methyl-4-(2-methylpropyl)benzeneacetic acid), one of the most-used, orally administered, non-steroidal anti-inflammatory products, is likewise topically applied (cf. U.S. Pat. No. 5,210,099 or U.S. Pat. No. 5,104,656).
The most related commercially available product to the present invention in its structure is presumably nimesulide or N-(4-nitro-2-phenoxyphenyl)methane-sulphonamide, which was first described in the document U.S. Pat. No. 3,840,597. In this patent, its possible topical application in the form of a cream or of a gel is already mentioned. Its topical application in the form of an ointment is additionally the subject of the more recent patent EP-A-0 532 900.
3-Amino-2-(4-methoxyphenoxy)pyridine, to which the present invention relates, is generally described on page 7 of the Patent Application WO 92/13842 as a theoretical possibility in a general formula of intermediary steps for the preparation of derivatives of the type N-(2-aryloxy-6-nitro)alkylsulphonamide. The preparation of this product and its features, however, are not expressly mentioned either in the said patent or in any other document, which is why it is a chemically novel product.
DESCRIPTION OF THE INVENTION
The object of the present invention is the preparation of 3-amino-2-(4-methoxyphenoxy)pyridine and its pharmaceutically suitable salts, among these particularly preferably the hydrochloride.
Besides3-amino-2-(4-methoxyphenoxy)pyridine, the present invention additionally relates to pharmaceutical compositions which contain therapeutically active amounts of the product 3-amino-2-(4-methoxyphenoxy)pyridine or of pharmaceutically suitable salts thereof and sufficient amounts of suitable auxiliaries. The preferred auxiliaries are found among those suitable for topical administration, in the form of creams, gels, ointments, unguents, eye drops and the like. The invention likewise includes the use of the product 3-amino-2-(4-methoxyphenoxy)pyridine or a pharmaceutically suitable salt thereof in the production of medicaments for the treatment of inflammatory syndromes.
Although3-amino-2-(4-methoxyphenoxy)pyridine, to which the present invention relates, can be administered orally, this product is especially preferred for topical application, which is why it has proven particularly suitable for the control of inflammatory skin and eye diseases, such as of allergic or photoallergic dermatitis, contact dermatitis, of sunburn, nettle-rash, eczema, atopic dermatitis, exfoliative dermatitis, psoriasis, etc.
The present invention makes available a preparation process for 3-amino-2-(4-methoxyphenoxy)pyridine, which is characterized in that 2-(4-methoxyphenoxy)-3-nitropyridine is catalytically hydrogenated in a suitable solvent. In a particular embodiment, the catalyst used is palladium on carbon and the solvent is ethyl acetate. The above starting material, 2-(4-methoxyphenoxy)-3-nitropyridine, is preferably obtained by reaction between 2-chloro-3-nitropyridine and the alkali metal salt of 4-methoxyphenol using toluene as a solvent. The pharmaceutically suitable salts of 3-amino-2-(4-met
REFERENCES:
patent: 3840597 (1974-10-01), Moore et al.
patent: 5104656 (1992-04-01), Seth et al.
patent: 5210099 (1993-05-01), Mody et al.
J. Invest. Dermat. J. M. Young, Tachyphylaxis in 12-0-Tetradecanoylphorbol Acetate- and Arachidonic Acid-Induced Ear Edema, vol. 80, pp. 48-52, 1983.
Proc. Soc. Ep. Biol. Med, C.A. Winter, et al, vol. III, pp. 544-547, 1962.
Aldoma Gustavo Enrique
Piatti Susana Elida
Handforth Investments Ltd.
Rotman Alan L.
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