EP1998772A2 - Use of e-3-[3-[n-(4-methoxybenzenesulfonyl)-n-isopropylamino]phenyl]-3-(3-pyridyl)propenohydroxamic acid for preparing a medicament for preventing and/or treating inflammatory skin pathologies - Google Patents

Use of e-3-[3-[n-(4-methoxybenzenesulfonyl)-n-isopropylamino]phenyl]-3-(3-pyridyl)propenohydroxamic acid for preparing a medicament for preventing and/or treating inflammatory skin pathologies

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Publication number
EP1998772A2
EP1998772A2 EP07731756A EP07731756A EP1998772A2 EP 1998772 A2 EP1998772 A2 EP 1998772A2 EP 07731756 A EP07731756 A EP 07731756A EP 07731756 A EP07731756 A EP 07731756A EP 1998772 A2 EP1998772 A2 EP 1998772A2
Authority
EP
European Patent Office
Prior art keywords
pharmaceutically acceptable
acid
compound
methoxybenzenesulfonyl
isopropylamino
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP07731756A
Other languages
German (de)
French (fr)
Inventor
Thibaud Biadatti
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Galderma Research and Development SNC
Original Assignee
Galderma Research and Development SNC
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Galderma Research and Development SNC filed Critical Galderma Research and Development SNC
Publication of EP1998772A2 publication Critical patent/EP1998772A2/en
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4406—Non condensed pyridines; Hydrogenated derivatives thereof only substituted in position 3, e.g. zimeldine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders

Definitions

  • E-3- [3- [N- (4-methoxybenzenesulfonyl) -N-isopropylamino] phenyl] -3- (3-pyridyl) propenohydroxamic acid for the preparation of a medicament for preventing and / or treat inflammatory skin diseases
  • the present invention relates to a novel use of E-3- [3- [N- (4-methoxybenzenesulfonyl) -N-isopropylamino] phenyl] -3- (3-pyridyl) propenohydroxamic acid, or a salt thereof pharmaceutically acceptable, pharmaceutically acceptable solvates or hydrates, for the preparation of a medicament for preventing and / or treating inflammatory skin diseases, and preferably eczema or psoriasis.
  • EP 1314721 discloses a family of propenohydroxamic acid derivatives, inhibitors of TNF-alpha converting enzyme, which are useful for the treatment or prevention of sepsis, rheumatoid arthritis, osteoarthritis, infectious diseases, autoimmune diseases, malignant tumors, collagen diseases, chronic ulcerative colitis, and insulin-independent diabetes.
  • E-3- [3- [N- (4-methoxybenzenesulfonyl) -N-isopropylamino] phenyl] -3- - pyridyl) propenohydroxamic is active to prevent and / or treat inflammatory skin diseases, and preferably eczema or psoriasis.
  • the present invention thus relates to the use of at least one compound chosen from the compound of formula (I) below:
  • pathologies include all forms of psoriasis, whether cutaneous, mucous or ungual, psoriatic arthritis, or atopy skin, such as eczema or respiratory atopy or gingival hypertrophy.
  • the pharmaceutically acceptable salts of the compound of formula (I) include those with inorganic or organic acids such as hydrochloric, hydrobromic, sulfuric, phosphoric, nitric, picric, oxalic acid, sufonic acids such as methanesulfonic acid, benzenesulphonic acid, and the like.
  • the salts of the compounds of formula (I) also include salts with organic or inorganic bases, for example the alkali metal salts, such as lithium, sodium or potassium salts.
  • hydrate of a compound of formula (I) is meant the combination of this compound with one or more molecules of water.
  • solvate of a compound of formula (I) is meant the association resulting from the attachment of a solvent to the crystals of compound of formula (I) formed in the presence of this solvent.
  • the compound (I), or a pharmaceutically acceptable salt thereof or a pharmaceutically acceptable or hydrated solvate thereof should be formulated into a pharmaceutical or dermatological composition.
  • the present invention therefore also relates to pharmaceutical compositions, preferably dermatological, comprising the compound (I), or a pharmaceutically acceptable salt thereof, or a pharmaceutically acceptable solvate or a hydrate thereof, for the treatment and / or the prevention of inflammatory skin diseases, and in particular all forms of psoriasis, whether cutaneous, mucous or ungual, and even psoriatic arthritis, or cutaneous atopy, such as eczema or respiratory atopy or else Gingival hypertrophy.
  • the present invention relates to pharmaceutical compositions, preferably dermatological, comprising the compound (I), or a pharmaceutically acceptable salt thereof, or one of its pharmaceutically acceptable solvates or one of its hydrates, preferably for the treatment and / or the prevention of eczema or psoriasis.
  • compositions may be intended and therefore suitable for oral, topical, enteral, parenteral, ocular, sublingual, inhaled, subcutaneous, intramuscular, intravenous, transdermal, local or rectal administration.
  • the compound (I) optionally in the form of a pharmaceutically acceptable salt, solvate and / or hydrate, alone or in combination with another active ingredient, may be administered in unit dosage form, in admixture with carriers or conventional pharmaceutical excipients, animals and humans.
  • the pharmaceutical composition is packaged in a form suitable for oral or topical administration.
  • compositions according to the invention contain the compound (I), or a pharmaceutically acceptable salt thereof, pharmaceutically acceptable solvates or hydrates, in an amount sufficient to obtain the desired prophylactic or therapeutic effect.
  • the dosage varies with the age, sex and weight of the patient.
  • the compound (I), or a salt thereof, solvates or hydrates will preferably be administered at a rate of from 0.01 to 100 mg / kg and per day, advantageously from 0.01 to 50 mg / kg and per day. It is also possible to administer such doses in 2 to 4 daily administrations. Although these dosages are examples of average situations, there may be special cases where higher dosages or lower are appropriate; such assays also belong to the invention.
  • compositions according to the invention comprise a physiologically acceptable carrier or at least one pharmaceutically acceptable excipient, chosen according to the pharmaceutical form, preferably the dermatological form, desired and the chosen mode of administration.
  • physiologically acceptable carrier and pharmaceutically acceptable excipient are meant respectively a carrier and excipient compatible with the skin, mucous membranes and integuments.
  • the pharmaceutical or dermatological composition may be in the form of tablets, capsules, dragees, pills, syrups, suspensions, solutions, powders, granules, emulsions, capsules, microspheres or nanospheres or lipid or polymeric vesicles for controlled release.
  • the composition may be in the form of solutions or suspensions for infusion or injection.
  • the active ingredient may be mixed with at least one inert diluent, such as sucrose, lactose or starch.
  • other additives such as a lubricant such as magnesium stearate, may be added.
  • a buffer may be added.
  • an inert diluent such as water may be used.
  • the pharmaceutical composition according to the invention is more particularly intended for the treatment of skin and mucous membranes and may be in the form of ointments, creams, milks, ointments, powders, impregnated swabs, syndets, solutions, gels, sprays, mousses, suspensions, lotions, sticks, shampoos, or washing bases. It may also be in the form of suspensions of microspheres or nanospheres or lipid or polymeric vesicles or polymeric patches and hydrogels allowing controlled release.
  • This topical composition may be in anhydrous form, in aqueous form or in the form of an emulsion.
  • the compound (I), or a salt, solvate or hydrate thereof when it is administered orally, is administered at a rate of 0.01 to 100 mg / kg and per day, advantageously from 0.01 to 50 mg / kg and per day.
  • the compound (I), or a salt thereof, solvates or hydrates, when administered topically is used at a concentration generally of between 0.001 and 10% by weight, preferably between 0.01 and 5% by weight. , relative to the total weight of the composition.
  • compositions as described above may therefore contain inert or even pharmacodynamically active additives, or combinations of these additives, and especially: wetting agents;
  • UV-A and UV-B filters are UV-A and UV-B filters
  • antioxidants such as ⁇ -tocopherol, butylhydroxyanisole or butylhydroxytoluene, superoxide dismutase, ubiquinol or certain metal chelators;
  • depigmenting agents such as hydroquinone, azelaic acid, caffeic acid or kojic acid;
  • moisturizing agents such as glycerol, PEG 400, thiamorpholinone and its derivatives or urea
  • moisturizing agents such as glycerol, PEG 400, thiamorpholinone and its derivatives or urea
  • antiseborrhoeic or antiacne agents such as S-carboxymethylcysteine, S-benzylcysteamine, their salts or derivatives, or benzoyl peroxide
  • moisturizing agents such as glycerol, PEG 400, thiamorpholinone and its derivatives or urea
  • antiseborrhoeic or antiacne agents such as S-carboxymethylcysteine, S-benzylcysteamine, their salts or derivatives, or benzoyl peroxide
  • antibiotics such as erythromycin and its esters, neomycin, clindamycin and its esters, tetracyclines;
  • antifungal agents such as ketoconazole or polymethylene-4,5-isothiazolidones-3; agents that promote hair regrowth, such as Minoxidil (2,4-diamino-6-piperidino-pyrimidine-3-oxide) and its derivatives, Diazoxide (7-chloro-3-methyl-1,2,4-benzothiadiazine) -1,1-dioxide) and phenytoin (5,4-diphenylimidazolidine 2,4-dione);
  • nonsteroidal anti-inflammatory agents carotenoids and, in particular, ⁇ -carotene;
  • anti-psoriatic agents such as anthralin and its derivatives
  • retinoids that is to say ligands of the RAR or RXR receptors, natural or synthetic;
  • ⁇ -hydroxy acids and ⁇ -keto acids or their derivatives such as lactic, malic, citric, glycolic, mandelic, tartaric, glyceric or ascorbic acids, as well as their salts, amides or esters, or ⁇ -hydroxy acids or their derivatives, such as salicylic acid and its salts, amides or esters;
  • ion channel blockers such as potassium channels
  • compositions in combination with medicaments known to interfere with the immune system (for example cyclosporin, FK 506, glucocorticoids, monoclonal antibodies, soluble receptors, cytokines or of growth ).
  • medicaments known to interfere with the immune system for example cyclosporin, FK 506, glucocorticoids, monoclonal antibodies, soluble receptors, cytokines or of growth .
  • test compound is dissolved in the arachidonic acid (AA) solution at the final concentration, and tested at concentrations of 0.1, 0.3 and 1%. 20 ⁇ l of the solution are applied on the inside of the right ear.
  • AA arachidonic acid
  • the thickness of the ear is measured at T + 1h T + 2h and T + 4h.
  • Indomethacin (negative control) at 5% inhibits ear edema due to arachidonic acid by 92% (***).
  • W3646 at 0.1%, 0.3% and 1% reduces ear edema by 16% (NS), 49% (*) and 71% (**) respectively with dose-dependent activity.

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  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Dermatology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)

Abstract

The invention relates to the use of E-3-[3-[N-(4-methoxybenzenesulfonyl)-N-isopropylamino]phenyl]-3-(3-pyridyl)propenohydroxamic acid of formula (I), or a pharmaceutically acceptable salt, pharmaceutically acceptable solvate or hydrate thereof, for preparing a medicament for preventing and/or treating inflammatory skin pathologies. The invention also relates to pharmaceutical, especially dermatological, compositions, comprising E-3-[3-[N-(4-methoxybenzenesulfonyl)-N-isopropylamino]phenyl]-3-(3-pyridyl)propenohydroxamic acid, or a pharmaceutically acceptable salt, pharmaceutically acceptable solvate, or hydrate thereof, for treating and/or preventing inflammatory skin pathologies.

Description

Utilisation de l'acide E-3-[3-[N-(4-méthoxybenzenesulfonyl)-N- isopropylamino]phényl]-3-(3-pyridyl)propenohydroxamique pour la préparation d'un médicament destiné à prévenir et/ou à traiter les pathologies inflammatoires cutanées Use of E-3- [3- [N- (4-methoxybenzenesulfonyl) -N-isopropylamino] phenyl] -3- (3-pyridyl) propenohydroxamic acid for the preparation of a medicament for preventing and / or treat inflammatory skin diseases
La présente invention concerne une nouvelle utilisation de l'acide E-3-[3-[N-(4- méthoxybenzenesulfonyl)-N-isopropylamino]phényl]-3- (3-pyridyl) propenohydroxamique, ou d'un de ses sels pharmaceutiquement acceptables, solvats pharmaceutiquement acceptables ou hydrates, pour la préparation d'un médicament destiné à prévenir et/ou à traiter des pathologies inflammatoires cutanées, et préférentiellement l'eczéma ou le psoriasis.The present invention relates to a novel use of E-3- [3- [N- (4-methoxybenzenesulfonyl) -N-isopropylamino] phenyl] -3- (3-pyridyl) propenohydroxamic acid, or a salt thereof pharmaceutically acceptable, pharmaceutically acceptable solvates or hydrates, for the preparation of a medicament for preventing and / or treating inflammatory skin diseases, and preferably eczema or psoriasis.
La demande de brevet EP 1314721 décrit une famille de dérivés d'acide propenohydroxamique, inhibiteurs de l'enzyme de conversion du TNF-alpha, qui sont utiles pour le traitement ou la prévention de la septicémie, de l'arthrite rhumatoïde, de l'ostéoarthrite, de maladies infectieuses, de maladies auto-immunes, de tumeurs malines, de maladies du collagène, de colites ulcéreuses chroniques, et de diabètes indépendants de l'insuline.EP 1314721 discloses a family of propenohydroxamic acid derivatives, inhibitors of TNF-alpha converting enzyme, which are useful for the treatment or prevention of sepsis, rheumatoid arthritis, osteoarthritis, infectious diseases, autoimmune diseases, malignant tumors, collagen diseases, chronic ulcerative colitis, and insulin-independent diabetes.
II a maintenant été trouvé, de façon inattendue, que l'un de ces composés, à savoir l'acide E-3-[3-[N-(4-méthoxybenzenesulfonyl)-N-isopropylamino]phényl]-3-(3- pyridyl)propenohydroxamique, est actif pour prévenir et/ou traiter des pathologies inflammatoires cutanées, et préférentiellement l'eczéma ou le psoriasis.It has now been found, unexpectedly, that one of these compounds, namely E-3- [3- [N- (4-methoxybenzenesulfonyl) -N-isopropylamino] phenyl] -3- - pyridyl) propenohydroxamic, is active to prevent and / or treat inflammatory skin diseases, and preferably eczema or psoriasis.
La présente invention se rapporte donc à l'utilisation d'au moins un composé choisi parmi le composé de formule (I) suivante:The present invention thus relates to the use of at least one compound chosen from the compound of formula (I) below:
(I) ∞rrespondant à l'exemple 17(1) (composé 88) de EP 1314721, à savoir l'acide E-3- [3-[N-(4-méthoxybenzenesulfonyl)-N-isopropylamino]phényl]-3-(3- pyridyl)propenohydroxamique et nommé par la suite composé (I), ses sels pharmaceutiquement acceptables, ses solvats pharmaceutiquement acceptables et ses hydrates, pour la préparation d'un médicament destiné à prévenir et/ou à traiter les pathologies inflammatoires cutanées. Ces pathologies sont notamment toutes les formes de psoriasis, qu'il soit cutané, muqueux ou unguéal, le rhumatisme psoriasique, ou encore l'atopie cutanée, telle que l'eczéma ou l'atopie respiratoire ou encore l'hypertrophie gingivale.(I) Corresponding to Example 17 (1) (Compound 88) of EP 1314721, namely E-3- [3- [N- (4-methoxybenzenesulfonyl) -N-isopropylamino] phenyl] -3- (3) - pyridyl) propenohydroxamic and subsequently named compound (I), its pharmaceutically acceptable salts, its pharmaceutically acceptable solvates and its hydrates, for the preparation of a medicament for preventing and / or treating inflammatory skin diseases. These pathologies include all forms of psoriasis, whether cutaneous, mucous or ungual, psoriatic arthritis, or atopy skin, such as eczema or respiratory atopy or gingival hypertrophy.
Les sels du composé de formule (I) pharmaceutiquement acceptables comprennent ceux avec des acides minéraux ou organiques tels que l'acide chlorhydrique, bromhydrique, sulfurique, phosphorique, nitrique, picrique, oxalique, les acides sufoniques comme l'acide méthanesulfonique, benzènesulfonique, p- toluènesulfonique, mésitylènesulfonique ou naphtalènesulfonique, l'acide tartrique, dibenzoyltartrique, mandélique, acétique, propionique, lactique, citrique, succinique, fumarique, maléique, malonique, phthalique ou camphosulfonique, et de préférence l'acide acétique, maléique, citrique, tartrique, méthanesulfonique, phosphorique, nitrique, sulfurique, bromhydrique, chlorhydrique.The pharmaceutically acceptable salts of the compound of formula (I) include those with inorganic or organic acids such as hydrochloric, hydrobromic, sulfuric, phosphoric, nitric, picric, oxalic acid, sufonic acids such as methanesulfonic acid, benzenesulphonic acid, and the like. toluenesulphonic, mesitylenesulphonic or naphthalenesulphonic acid, tartaric acid, dibenzoyltartric acid, mandelic acid, acetic acid, propionic acid, lactic acid, citric acid, succinic acid, fumaric acid, maleic acid, malonic acid, phthalic acid or camphorsulfonic acid, and preferably acetic acid, maleic acid, citric acid, tartaric acid, methanesulfonic, phosphoric, nitric, sulfuric, hydrobromic, hydrochloric.
Les sels des composés de formule (I) comprennent également des sels avec des bases organiques ou minérales, par exemple les sels des métaux alcalins, comme les sels de lithium, de sodium, de potassium.The salts of the compounds of formula (I) also include salts with organic or inorganic bases, for example the alkali metal salts, such as lithium, sodium or potassium salts.
Par hydrate d'un composé de formule (I), on entend la combinaison de ce composé avec une ou plusieurs molécules d'eau.By hydrate of a compound of formula (I) is meant the combination of this compound with one or more molecules of water.
Par solvat d'un composé de formule (I), on entend l'association résultant de la fixation d'un solvant sur les cristaux de composé de formule (I) formés en présence de ce solvant.By solvate of a compound of formula (I) is meant the association resulting from the attachment of a solvent to the crystals of compound of formula (I) formed in the presence of this solvent.
Pour son utilisation en tant que médicament, le composé (I), ou un de ses sels pharmaceutiquement acceptables ou un de ses solvats pharmaceutiquement acceptables ou hydrates, doit être formulé en composition pharmaceutique ou dermatologique. La présente invention a donc également pour objet des compositions pharmaceutiques, préférentiellement dermatologiques, comprenant le composé (I), ou un de ses sels pharmaceutiquement acceptables, ou un de ses solvats pharmaceutiquement acceptables ou un de ses hydrates, pour le traitement et/ou la prévention des pathologies inflammatoires cutanées, et notamment toutes les formes de psoriasis, qu'il soit cutané, muqueux ou unguéal, et même le rhumatisme psoriasique, ou encore l'atopie cutanée, telle que l'eczéma ou l'atopie respiratoire ou encore l'hypertrophie gingivale.For use as a medicament, the compound (I), or a pharmaceutically acceptable salt thereof or a pharmaceutically acceptable or hydrated solvate thereof, should be formulated into a pharmaceutical or dermatological composition. The present invention therefore also relates to pharmaceutical compositions, preferably dermatological, comprising the compound (I), or a pharmaceutically acceptable salt thereof, or a pharmaceutically acceptable solvate or a hydrate thereof, for the treatment and / or the prevention of inflammatory skin diseases, and in particular all forms of psoriasis, whether cutaneous, mucous or ungual, and even psoriatic arthritis, or cutaneous atopy, such as eczema or respiratory atopy or else Gingival hypertrophy.
La présente invention a pour objet des compositions pharmaceutiques, de préférence dermatologiques, comprenant le composé (I), ou un de ses sels pharmaceutiquement acceptables, ou un de ses solvats pharmaceutiquement acceptables ou un de ses hydrates, préférentiellement pour le traitement et/ou la prévention de l'eczéma ou du psoriasis.The present invention relates to pharmaceutical compositions, preferably dermatological, comprising the compound (I), or a pharmaceutically acceptable salt thereof, or one of its pharmaceutically acceptable solvates or one of its hydrates, preferably for the treatment and / or the prevention of eczema or psoriasis.
De telles compositions peuvent être destinées, et donc adaptées, à une administration par voie orale, topique, entérale, parentérale, oculaire, sublinguale, inhalée, sous-cutanée, intramusculaire, intraveineuse, transdermique, locale ou rectale. Le composé (I), éventuellement sous la forme d'un sel, solvat et/ou hydrate pharmaceutiquement acceptable, seul ou en association avec un autre principe actif, peut être administré sous une forme unitaire d'administration, en mélange avec des supports ou excipients pharmaceutiques classiques, aux animaux et aux êtres humains. De préférence, la composition pharmaceutique est conditionnée sous une forme convenant à une administration par voie orale ou topique.Such compositions may be intended and therefore suitable for oral, topical, enteral, parenteral, ocular, sublingual, inhaled, subcutaneous, intramuscular, intravenous, transdermal, local or rectal administration. The compound (I), optionally in the form of a pharmaceutically acceptable salt, solvate and / or hydrate, alone or in combination with another active ingredient, may be administered in unit dosage form, in admixture with carriers or conventional pharmaceutical excipients, animals and humans. Preferably, the pharmaceutical composition is packaged in a form suitable for oral or topical administration.
Les compositions selon l'invention contiennent le composé (I), ou un de ses sels pharmaceutiquement acceptables, solvats pharmaceutiquement acceptables ou hydrates, en quantité suffisante pour obtenir l'effet prophylactique ou thérapeutique souhaité. La posologie utile varie selon l'âge, le sexe et le poids du patient. Le composé (I), ou un de ses sels, solvats ou hydrates sera, de préférence, administré à raison de 0,01 à 100 mg/kg et par jour, avantageusement de 0,01 à 50 mg/kg et par jour. Il est également possible d'administrer de telles doses, en 2 à 4 administrations quotidiennes. Bien que ces dosages soient des exemples de situations moyennes, il peut y avoir des cas particuliers où des dosages plus élevés ou plus faibles sont appropriés ; de tels dosages appartiennent également à l'invention.The compositions according to the invention contain the compound (I), or a pharmaceutically acceptable salt thereof, pharmaceutically acceptable solvates or hydrates, in an amount sufficient to obtain the desired prophylactic or therapeutic effect. The dosage varies with the age, sex and weight of the patient. The compound (I), or a salt thereof, solvates or hydrates, will preferably be administered at a rate of from 0.01 to 100 mg / kg and per day, advantageously from 0.01 to 50 mg / kg and per day. It is also possible to administer such doses in 2 to 4 daily administrations. Although these dosages are examples of average situations, there may be special cases where higher dosages or lower are appropriate; such assays also belong to the invention.
Les compositions selon l'invention comprennent un support physiologiquement acceptable ou au moins un excipient pharmaceutiquement acceptable, choisi selon la forme pharmaceutique, de préférence dermatologique, souhaitée et le mode d'administration choisi.The compositions according to the invention comprise a physiologically acceptable carrier or at least one pharmaceutically acceptable excipient, chosen according to the pharmaceutical form, preferably the dermatological form, desired and the chosen mode of administration.
Par support physiologiquement acceptable et excipient pharmaceutiquement acceptable, on entend respectivement un support et un excipient compatibles avec la peau, les muqueuses et les phanères.By physiologically acceptable carrier and pharmaceutically acceptable excipient is meant respectively a carrier and excipient compatible with the skin, mucous membranes and integuments.
Pour une administration par voie orale, la composition pharmaceutique ou dermatologique, peut se présenter sous la forme de comprimés, de gélules, de dragées, de pilules, de sirops, de suspensions, de solutions, de poudres, de granulés, d'émulsions, de capsules, de microsphères ou nanosphères ou vésicules lipidiques ou polymériques permettant une libération contrôlée. Par voie parentérale, la composition peut se présenter sous forme de solutions ou suspensions pour perfusion ou pour injection. Pour obtenir une composition solide pour administration orale, le principe actif pourra être mélangé avec au moins un diluant inerte, tel que le sucrose, le lactose ou l'amidon. En général, d'autres additifs, tel qu'un lubrifiant comme le stéarate de magnésium, pourront être ajoutés. Dans le cas de capsules, comprimés ou pilules notamment, un tampon pourra être ajouté. Dans le cas des compositions liquides orales, un diluant inerte tel que de l'eau pourra être utilisé.For an oral administration, the pharmaceutical or dermatological composition may be in the form of tablets, capsules, dragees, pills, syrups, suspensions, solutions, powders, granules, emulsions, capsules, microspheres or nanospheres or lipid or polymeric vesicles for controlled release. Parenterally, the composition may be in the form of solutions or suspensions for infusion or injection. To obtain a solid composition for oral administration, the active ingredient may be mixed with at least one inert diluent, such as sucrose, lactose or starch. In general, other additives, such as a lubricant such as magnesium stearate, may be added. In the case of capsules, tablets or pills in particular, a buffer may be added. In the case of oral liquid compositions, an inert diluent such as water may be used.
Par voie topique, la composition pharmaceutique selon l'invention est plus particulièrement destinée au traitement de la peau et des muqueuses et peut se présenter sous forme d'onguents, de crèmes, de laits, de pommades, de poudres, de tampons imbibés, de syndets, de solutions, de gels, de sprays, de mousses, de suspensions, de lotions, de sticks, de shampoings, ou de bases lavantes. Elle peut également se présenter sous forme de suspensions de microsphères ou nanosphères ou vésicules lipidiques ou polymériques ou de patches polymériques et d'hydrogels permettant une libération contrôlée. Cette composition par voie topique peut se présenter sous forme anhydre, sous forme aqueuse ou sous la forme d'une émulsion. Le composé (I), ou un de ses sels, solvats ou hydrates, lorsqu'il est administré par voie orale est administré à raison de 0,01 à 100 mg/kg et par jour, avantageusement de 0,01 à 50 mg/kg et par jour.Topically, the pharmaceutical composition according to the invention is more particularly intended for the treatment of skin and mucous membranes and may be in the form of ointments, creams, milks, ointments, powders, impregnated swabs, syndets, solutions, gels, sprays, mousses, suspensions, lotions, sticks, shampoos, or washing bases. It may also be in the form of suspensions of microspheres or nanospheres or lipid or polymeric vesicles or polymeric patches and hydrogels allowing controlled release. This topical composition may be in anhydrous form, in aqueous form or in the form of an emulsion. The compound (I), or a salt, solvate or hydrate thereof when it is administered orally, is administered at a rate of 0.01 to 100 mg / kg and per day, advantageously from 0.01 to 50 mg / kg and per day.
Le composé (I), ou un de ses sels, solvats ou hydrates, lorsqu'il est administré par voie topique est utilisé à une concentration généralement comprise entre 0,001 et 10% en poids, de préférence entre 0,01 et 5% en poids, par rapport au poids total de la composition.The compound (I), or a salt thereof, solvates or hydrates, when administered topically is used at a concentration generally of between 0.001 and 10% by weight, preferably between 0.01 and 5% by weight. , relative to the total weight of the composition.
On peut également utiliser, pour le traitement d'une pathologie inflammatoire cutanée, et plus particulièrement de l'eczéma ou du psoriasis, le composé (I), ou un de ses sels pharmaceutiquement acceptables ou un de ses solvats pharmaceutiquement acceptables ou hydrates, en association avec un autre principe actif.It is also possible to use, for the treatment of an inflammatory skin pathology, and more particularly eczema or psoriasis, the compound (I), or a pharmaceutically acceptable salt or a pharmaceutically acceptable or hydrated solvate thereof, association with another active ingredient.
Les compositions pharmaceutiques et dermatologiques telles que décrites précédemment peuvent donc contenir des additifs inertes, ou même pharmacodynamiquement actifs, ou des combinaisons de ces additifs, et notamment : - des agents mouillants ;The pharmaceutical and dermatological compositions as described above may therefore contain inert or even pharmacodynamically active additives, or combinations of these additives, and especially: wetting agents;
- des agents d'amélioration de la saveur ;- flavor enhancers;
- des agents conservateurs tels que les esters de l'acide parahydroxybenzoïque ;preserving agents such as esters of parahydroxybenzoic acid;
- des agents stabilisants ;stabilizing agents;
- des agents régulateurs d'humidité ; - des agents régulateurs de pH ;humidity regulating agents; pH regulating agents;
- des agents modificateurs de pression osmotique ;osmotic pressure modifying agents;
- des agents émulsionnants ;emulsifying agents;
- des filtres UV-A et UV-B ;UV-A and UV-B filters;
- des antioxydants, tels que l'α-tocophérol, le butylhydroxyanisole ou le butylhydroxytoluène, la super oxyde dismutase, l'ubiquinol ou certains chélatants de métaux ;antioxidants, such as α-tocopherol, butylhydroxyanisole or butylhydroxytoluene, superoxide dismutase, ubiquinol or certain metal chelators;
- des agents dépigmentants tels que l'hydroquinone, l'acide azélaïque, l'acide caféïque ou l'acide kojique ;depigmenting agents such as hydroquinone, azelaic acid, caffeic acid or kojic acid;
- des émollients ; - des agents hydratants comme le glycérol, le PEG 400, la thiamorpholinone, et ses dérivés ou l'urée ; des agents antiséborrhéiques ou antiacnéiques, tels que la S- carboxyméthylcystéine, la S-benzyl-cystéamine, leurs sels ou leurs dérivés, ou le peroxyde de benzoyle ;- emollients; moisturizing agents such as glycerol, PEG 400, thiamorpholinone and its derivatives or urea; antiseborrhoeic or antiacne agents, such as S-carboxymethylcysteine, S-benzylcysteamine, their salts or derivatives, or benzoyl peroxide;
- des antibiotiques comme l'érythromycine et ses esters, la néomycine, la clindamycine et ses esters, les tétracyclines ;antibiotics such as erythromycin and its esters, neomycin, clindamycin and its esters, tetracyclines;
- des agents antifongiques tels que le kétoconazole ou les polyméthylène-4,5 isothiazolidones-3 ; - des agents favorisant la repousse des cheveux, comme le Minoxidil (2,4-diamino- 6-pipéridino-pyrimidine-3-oxyde) et ses dérivés, le Diazoxide (7-chloro-3-méthyl 1,2,4-benzothiadiazine-1,1-dioxyde) et le Phénytoïne (5,4-diphényl-imidazolidine 2,4-dione) ;antifungal agents such as ketoconazole or polymethylene-4,5-isothiazolidones-3; agents that promote hair regrowth, such as Minoxidil (2,4-diamino-6-piperidino-pyrimidine-3-oxide) and its derivatives, Diazoxide (7-chloro-3-methyl-1,2,4-benzothiadiazine) -1,1-dioxide) and phenytoin (5,4-diphenylimidazolidine 2,4-dione);
- des agents anti-inflammatoires non stéroïdiens ; - des caroténoïdes et, notamment, le β-carotène ;nonsteroidal anti-inflammatory agents; carotenoids and, in particular, β-carotene;
- des agents anti-psoriatiques tels que l'anthraline et ses dérivés;anti-psoriatic agents such as anthralin and its derivatives;
- des acides eicosa-5,8,11,14-tétraynoïque et eicosa-5,8,11-triynoïque, leurs esters et amides ;- eicosa-5,8,11,14-tetraynoic and eicosa-5,8,11-triynoic acids, their esters and amides;
- des rétinoïdes, c'est à dire des ligands des récepteurs RAR ou RXR, naturels ou synthétiques ;retinoids, that is to say ligands of the RAR or RXR receptors, natural or synthetic;
- des ligands des récepteurs VDR ;ligands of VDR receptors;
- des corticostéroïdes ou des œstrogènes ;- corticosteroids or estrogens;
- des α-hydroxy acides et des α-céto acides ou leurs dérivés, tels que les acides lactique, malique, citrique, glycolique, mandélique, tartrique, glycérique, ascorbique, ainsi que leurs sels, amides ou esters, ou des β-hydroxy acides ou leurs dérivés, tels que l'acide salicylique ainsi que ses sels, amides ou esters ;α-hydroxy acids and α-keto acids or their derivatives, such as lactic, malic, citric, glycolic, mandelic, tartaric, glyceric or ascorbic acids, as well as their salts, amides or esters, or β-hydroxy acids or their derivatives, such as salicylic acid and its salts, amides or esters;
- des bloqueurs de canaux ioniques tels que les canaux potassiques ;ion channel blockers such as potassium channels;
- ou encore, plus particulièrement pour les compositions pharmaceutiques, en association avec des médicaments connus pour interférer avec le système immunitaire (par exemple, la cyclosporine, le FK 506, les glucocorticoïdes, les anticorps monoclonaux, les récepteurs solubles, les cytokines ou les facteurs de croissance...).or, more particularly for the pharmaceutical compositions, in combination with medicaments known to interfere with the immune system (for example cyclosporin, FK 506, glucocorticoids, monoclonal antibodies, soluble receptors, cytokines or of growth ...).
Bien entendu, l'homme du métier veillera à choisir le ou les éventuels composés à ajouter à ces compositions de telle manière que l'effet sur le psoriasis ou l'eczéma désiré ne soit pas, ou substantiellement pas altéré par l'addition envisagée.Of course, those skilled in the art will take care to choose the optional compound (s) to be added to these compositions in such a way that the effect on psoriasis or the desired eczema is not, or not substantially, impaired by the intended addition.
L'étude des propriétés du composé de formule (I) a montré que le composé de formule (I), ainsi que ses sels, solvats ou hydrates pharmaceutiquement acceptables ne sont pas toxiques, et sont doués d'une activité anti-inflammatoire dans le traitement de l'eczéma et du psoriasis, qui se manifeste aussi bien par voie topique que orale.The study of the properties of the compound of formula (I) has shown that the compound of formula (I), as well as its pharmaceutically acceptable salts, solvates or hydrates are not toxic, and are endowed with an anti-inflammatory activity in the treatment of eczema and psoriasis, which is manifested both topically and orally.
EXEMPLE 1 : COMPOSITIONSEXAMPLE 1: COMPOSITIONS
A- VOIE ORALEA- ORAL WAY
Comprimé de 0.2 g0.2 g tablet
- Composé de formule (I) 0,001 g- Compound of formula (I) 0.001 g
- Amidon 0,114 g- 0.114 g starch
- Phosphate bicalcique 0,020 g- Dicalcium phosphate 0.020 g
- Silice 0,020 g- Silica 0.020 g
- Lactose 0,030 g- Lactose 0.030 g
- Talc 0,010 g- Talc 0.010 g
- Stéarate de magnésium 0,005 g- magnesium stearate 0.005 g
B- VOIE TOPIQUEB- TOPICAL ROUTE
(a) Onguent(a) Ointment
-Composé de formule (I) 0,30 g - Vaseline blanche codex qsp 100 g-Compound of formula (I) 0.30 g - white Vaseline codex qs 100 g
(b) Lotion(b) Lotion
- Composé de formule (I) 0,10 g- Compound of formula (I) 0.10 g
- Polyéthylène glycol (PEG 400) 69,90 g- Polyethylene glycol (PEG 400) 69.90 g
- Ethanol à 95% 30,00 g- 95% ethanol 30.00 g
EXEMPLE 2 : Evaluation de l'activité anti-inflammatoire de W3646 (composé (I)) après une application topique unique dans le test de l'oedème de l'oreille de souris induit par l'acide arachidonique sur les souris Balb/cEXAMPLE 2 Evaluation of the Anti-inflammatory Activity of W3646 (Compound (I)) After a Unique Topical Application in the Arachidonic Acid-Induced Mouse Ear Edema Test on Balb / c Mice
L'acide arachidonique est dissous dans un mélange THF/Methanol à 4%Arachidonic acid is dissolved in 4% THF / Methanol
Traitement:Treatment:
Le composé à tester est dissous dans la solution d'acide arachidonique (AA) à la concentration finale, et testé aux concentrations de 0.1 , 0.3 et 1%. 20μl de la solution sont appliqués sur la face interne de l'oreille droite.The test compound is dissolved in the arachidonic acid (AA) solution at the final concentration, and tested at concentrations of 0.1, 0.3 and 1%. 20 μl of the solution are applied on the inside of the right ear.
L'épaisseur de l'oreille est mesurée à T+1h T+2h et T+4h.The thickness of the ear is measured at T + 1h T + 2h and T + 4h.
Résultats :Results:
Les résultats sont en figure 1. Une heure après l'application, la solution de l'acide arachidonique à 4% induit une augmentation de l'épaisseur de l'oreille de 76%.The results are in Figure 1. One hour after application, the 4% arachidonic acid solution induced an increase in the thickness of the ear of 76%.
L'indométacine (contrôle négatif) à 5% inhibe l'œdème de l'oreille dû à l'acide arachidonique de 92% (***). W3646 à 0.1%, 0.3% et 1% réduit l'œdème de l'oreille respectivement de 16% (NS), 49% (*) et 71% (**) avec une activité dose dépendante. Indomethacin (negative control) at 5% inhibits ear edema due to arachidonic acid by 92% (***). W3646 at 0.1%, 0.3% and 1% reduces ear edema by 16% (NS), 49% (*) and 71% (**) respectively with dose-dependent activity.

Claims

W3646 montre donc un effet anti-inflammatoire dans le modèle de l'œdème de l'oreille de souris induit par l'acide arachidonique.EXEMPLE 3 : Evaluation de l'activité anti-inflammatoire de W3646 (composé (I)) après une application topique unique dans le test de l'œdème de l'oreille de souris induit par le TPA sur les souris Balb/cTraitement :L'oedème est induit par application unique de 20μl de TPA dissous dans l'acétone à0.01%.Le composé à tester est dilué dans la solution de TPA et appliqué à une concentration de 0.1%, 0.3% et 1%. Un contrôle positif, le valérate de β-méthasone (VdB) est également testé.L'épaisseur de l'oreille de souris est mesurée à T+6h.Résultats :Les résultats sont en figure 2.Après une application unique topique du contrôle positif valérate de bétaméthasone (0.01%) dilué dans la solution de TPA, une réduction de l'œdème de l'oreille de 93 %(***) est observée.W3646 a un fort effet anti-inflammatoire dose-dépendant, et réduit l'oedème de l'oreille induit par le TPA de 26% (NS) (à 0.1%), 53 %(**) (à 0.3%) et 79% (***) (à 1%). REVENDICATIONS W3646 thus shows an anti-inflammatory effect in the model of arachidonic acid-induced mouse ear edema. EXAMPLE 3: Evaluation of the anti-inflammatory activity of W3646 (compound (I)) after an application single topical in the TPA-induced mouse ear edema test in Balb / c treatment mice: The edema is induced by a single application of 20 μl of TPA dissolved in 0.01% acetone. to be tested is diluted in the TPA solution and applied at a concentration of 0.1%, 0.3% and 1%. A positive control, β-methasone valerate (VdB) is also tested.The thickness of the mouse ear is measured at T + 6h.Results: The results are in Figure 2.After a single topical application of positive control betamethasone valerate (0.01%) diluted in the TPA solution, a reduction in ear edema of 93% (***) is observed.W3646 has a strong dose-dependent anti-inflammatory effect, and reduces TPA-induced ear edema of 26% (NS) (at 0.1%), 53% (**) (at 0.3%) and 79% (***) (at 1%). CLAIMS
1. Utilisation d'au moins un composé choisi parmi l'acide E-3-[3-[N-(4- méthoxybenzenesulfonyl)-N-isopropylamino]phényl]-3-(3- pyridyl)propenohydroxamique de formule (I) :Use of at least one compound selected from E-3- [3- [N- (4-methoxybenzenesulfonyl) -N-isopropylamino] phenyl] -3- (3-pyridyl) propenohydroxamic acid of formula (I) :
un de ses sels pharmaceutiquement acceptables, un de ses solvats pharmaceutiquement acceptables et un de ses hydrates, pour la préparation d'un médicament destiné à prévenir et/ou à traiter les pathologies inflammatoires cutanées. one of its pharmaceutically acceptable salts, one of its pharmaceutically acceptable solvates and one of its hydrates, for the preparation of a medicament for preventing and / or treating inflammatory skin diseases.
2. Utilisation selon la revendication 1 , caractérisée en ce que les pathologies inflammatoires cutanées sont choisies parmi l'eczéma et le psoriasis.2. Use according to claim 1, characterized in that the inflammatory skin diseases are selected from eczema and psoriasis.
3. Utilisation selon la revendication 1 ou 2 caractérisée en ce que le médicament est adapté à une administration orale.3. Use according to claim 1 or 2 characterized in that the drug is suitable for oral administration.
4. Utilisation selon la revendication 1 ou 2 caractérisée en ce que le médicament est adapté à une administration topique.4. Use according to claim 1 or 2 characterized in that the drug is suitable for topical administration.
5. Utilisation d'une composition pharmaceutique comprenant, dans un support physiologiquement acceptable, au moins un composé choisi parmi l'acide E-3-[3-[N- (4-méthoxybenzenesulfonyl)-N-isopropylamino]phényl]-3-(3- pyridyl)propenohydroxamique de formule (I) : 5. Use of a pharmaceutical composition comprising, in a physiologically acceptable support, at least one compound chosen from E-3- [3- [N- (4-methoxybenzenesulfonyl) -N-isopropylamino] phenyl] -3- (3-pyridyl) propenohydroxamic acid of formula (I):
un de ses sels pharmaceutiquement acceptables, un de ses solvats pharmaceutiquement acceptables et un de ses hydrates, pour préparer un médicament destiné à prévenir et/ou traiter les pathologies inflammatoires cutanées choisies parmi l'eczéma et le psoriasis. one of its pharmaceutically acceptable salts, one of its pharmaceutically acceptable solvates and one of its hydrates, for preparing a medicament for preventing and / or treating cutaneous inflammatory pathologies chosen from eczema and psoriasis.
EP07731756A 2006-03-20 2007-03-16 Use of e-3-[3-[n-(4-methoxybenzenesulfonyl)-n-isopropylamino]phenyl]-3-(3-pyridyl)propenohydroxamic acid for preparing a medicament for preventing and/or treating inflammatory skin pathologies Withdrawn EP1998772A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0602428A FR2898495A1 (en) 2006-03-20 2006-03-20 USE OF E-3- (N-METHOXYBENZENESULFONYL) -N-ISOPROPYLAMINO-PHENYL) -3- (3-PYRIDYL) PROPENOHYDROXAMIC ACID FOR THE PREPARATION OF A MEDICAMENT FOR THE PREVENTION AND / OR TREATMENT OF SKIN INFLAMMATORY DISEASES
PCT/FR2007/050940 WO2007107664A2 (en) 2006-03-20 2007-03-16 Use of e-3-[3-[n-(4-methoxybenzenesulfonyl)-n-isopropylamino]phenyl]-3-(3-pyridyl)propenohydroxamic acid for preparing a medicament for preventing and/or treating inflammatory skin pathologies

Publications (1)

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EP1998772A2 true EP1998772A2 (en) 2008-12-10

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US (1) US20090088460A1 (en)
EP (1) EP1998772A2 (en)
CA (1) CA2645329A1 (en)
FR (1) FR2898495A1 (en)
WO (1) WO2007107664A2 (en)

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Publication number Priority date Publication date Assignee Title
US20040122011A1 (en) * 1998-12-23 2004-06-24 Pharmacia Corporation Method of using a COX-2 inhibitor and a TACE inhibitors as a combination therapy
CA2423733A1 (en) * 2000-08-31 2003-02-14 Terukage Hirata Novel propenohydroxamic acid derivatives

Non-Patent Citations (1)

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Title
See references of WO2007107664A2 *

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US20090088460A1 (en) 2009-04-02
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CA2645329A1 (en) 2007-09-27

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