EP1998772A2 - Verwendung von e-3-[3-[n-(4-methoxybenzensulfonyl)-n-isopropylamin]-phenyl]-3-(3-pyridyl)propenhydroxamsäure zur herstellung eines medikaments zur verhinderung und/oder behandlung entzündlicher hautkrankheiten - Google Patents

Verwendung von e-3-[3-[n-(4-methoxybenzensulfonyl)-n-isopropylamin]-phenyl]-3-(3-pyridyl)propenhydroxamsäure zur herstellung eines medikaments zur verhinderung und/oder behandlung entzündlicher hautkrankheiten

Info

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Withdrawn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
English (en)
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/de
Withdrawn legal-status Critical Current

Links

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.

Landscapes

  • 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)
EP07731756A 2006-03-20 2007-03-16 Verwendung von e-3-[3-[n-(4-methoxybenzensulfonyl)-n-isopropylamin]-phenyl]-3-(3-pyridyl)propenhydroxamsäure zur herstellung eines medikaments zur verhinderung und/oder behandlung entzündlicher hautkrankheiten Withdrawn EP1998772A2 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0602428A FR2898495A1 (fr) 2006-03-20 2006-03-20 Utilisation de l'acide e-3-(n-methoxybenzenesulfonyl)-n- isopropylamino phenyl)-3-(3-pyridyl)propenohydroxamique pour la preparation d'un medicament destine a prevenir et/ou a traiter les pathologies inflammatoires cutanees
PCT/FR2007/050940 WO2007107664A2 (fr) 2006-03-20 2007-03-16 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

Publications (1)

Publication Number Publication Date
EP1998772A2 true EP1998772A2 (de) 2008-12-10

Family

ID=37440904

Family Applications (1)

Application Number Title Priority Date Filing Date
EP07731756A Withdrawn EP1998772A2 (de) 2006-03-20 2007-03-16 Verwendung von e-3-[3-[n-(4-methoxybenzensulfonyl)-n-isopropylamin]-phenyl]-3-(3-pyridyl)propenhydroxamsäure zur herstellung eines medikaments zur verhinderung und/oder behandlung entzündlicher hautkrankheiten

Country Status (5)

Country Link
US (1) US20090088460A1 (de)
EP (1) EP1998772A2 (de)
CA (1) CA2645329A1 (de)
FR (1) FR2898495A1 (de)
WO (1) WO2007107664A2 (de)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
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
EP1314721A1 (de) * 2000-08-31 2003-05-28 Wakunaga Pharmaceutical Co., Ltd. Neue propenohydroxamsäure-derivate

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2007107664A2 *

Also Published As

Publication number Publication date
FR2898495A1 (fr) 2007-09-21
CA2645329A1 (fr) 2007-09-27
US20090088460A1 (en) 2009-04-02
WO2007107664A2 (fr) 2007-09-27
WO2007107664A3 (fr) 2008-03-20

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