EP1998779A2 - Verwendung von (3s)-n-hydroxy-4-({4-¦(4-hydroxy-2-butynyl)oxy]phenyl}sulfonyl)-2,2-dimethyl-3-thiomorpholin-carboxamid bzw. (s)-n-hydroxy-4-(4-but-2-ynyloxy-benzolsulfonyl) -2,2-dimethyl-thiomorpholin-3-carboxamid zur behandlung entzündlicher hautkrankheiten - Google Patents

Verwendung von (3s)-n-hydroxy-4-({4-¦(4-hydroxy-2-butynyl)oxy]phenyl}sulfonyl)-2,2-dimethyl-3-thiomorpholin-carboxamid bzw. (s)-n-hydroxy-4-(4-but-2-ynyloxy-benzolsulfonyl) -2,2-dimethyl-thiomorpholin-3-carboxamid zur behandlung entzündlicher hautkrankheiten

Info

Publication number
EP1998779A2
EP1998779A2 EP07731755A EP07731755A EP1998779A2 EP 1998779 A2 EP1998779 A2 EP 1998779A2 EP 07731755 A EP07731755 A EP 07731755A EP 07731755 A EP07731755 A EP 07731755A EP 1998779 A2 EP1998779 A2 EP 1998779A2
Authority
EP
European Patent Office
Prior art keywords
hydroxy
pharmaceutically acceptable
carboxamide
dimethyl
thiomorpholine
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Withdrawn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
EP07731755A
Other languages
English (en)
French (fr)
Inventor
Thibaud Biadatti
Marlène SCHUPPLI
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 EP1998779A2 publication Critical patent/EP1998779A2/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Withdrawn legal-status Critical Current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
    • A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
    • 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
    • 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
    • A61P17/06—Antipsoriatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]

Definitions

  • the present invention relates to a new use of a compound of formula (I) or a pharmaceutically acceptable salt thereof, pharmaceutically acceptable solvates or hydrates, for the preparation of a medicament for preventing and / or treating inflammatory pathologies cutaneous and preferentially eczema or psoriasis.
  • Patent application WO 00/44709 discloses a family of hydroxamic acid derivatives arylsulfonamide, inhibitors of TNF-alpha converting enzyme, which are useful for the treatment or prevention of arthritis, tumor metastasis, tissue ulceration, abnormal wound healing, aprodontal disease, transplant rejection, insulin resistance, bone disease and AIDS.
  • the present invention thus relates to the use of at least one compound chosen from the following compounds of formula (I):
  • R corresponds to a -CH3 radical or a CH 2 OH radical
  • their pharmaceutically acceptable salts their pharmaceutically acceptable solvates or their hydrates
  • a medicament for preventing and / or treating inflammatory skin diseases.
  • 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 invention relates more specifically to the use of (3S) -N-hydroxy-4 - ( ⁇ 4 - [(4-hydroxy-2-butynyl) oxy] phenyl ⁇ sulfonyl) -2,2-dimethyl-3-thiomorpholine carboxamide (or Apratastat) or (S) -N-Hydroxy-4- (4-but-2-ynyloxy-benzenesulfonyl) -2,2-dimethyl-thiomorpholine-3-carboxamide, a pharmaceutically acceptable salt thereof, pharmaceutically acceptable solvates or hydrates for the preparation of a medicament for preventing and / or treating inflammatory skin diseases.
  • the salts of the compounds of formula (I) according to the invention include salts with organic or inorganic bases, for example the alkali metal salts, such as the lithium, sodium and 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 compounds of formula (I), their pharmaceutically acceptable salts, their pharmaceutically acceptable solvates or their hydrates must be formulated into a pharmaceutical composition, preferably a dermatological composition.
  • compositions especially dermatological compositions, comprising at least one compound chosen from compounds of formula (I) in which R corresponds to a -CH3 radical or a CH 2 OH radical, their pharmaceutically acceptable salts, their pharmaceutically acceptable solvates and their hydrates, for the treatment and / or prevention of inflammatory skin diseases, and in particular all forms of psoriasis, whether it is cutaneous, mucous or ungual, and even psoriatic arthritis, or cutaneous atopy, such as eczema or respiratory atopy or gingival hypertrophy.
  • R corresponds to a -CH3 radical or a CH 2 OH radical
  • their pharmaceutically acceptable salts their pharmaceutically acceptable solvates and their hydrates
  • the present invention more particularly relates to pharmaceutical compositions, especially dermatological compositions, comprising at least one compound chosen from the compounds of formula (I), their pharmaceutically acceptable salts, their pharmaceutically acceptable solvates or their hydrates, preferentially 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 of formula (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 conventional pharmaceutical carriers or excipients to animals and humans.
  • the pharmaceutical composition is packaged in a form suitable for oral or topical administration.
  • compositions according to the invention comprise at least one compound of formula (I), or one of its pharmaceutically acceptable salts, 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 of formula (I), or one of its salts, 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 day. It is also possible to administer such doses in 2 to 4 daily administrations. Although these assays are examples of average situations, there may be special cases where higher or lower dosages 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, in particular the dermatological form, desired and the mode of administration chosen.
  • 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.
  • 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 in the case of capsules, tablets or pills in particular.
  • an inert diluent such as water may be used.
  • the pharmaceutical composition according to the invention is more particularly intended for the treatment of the skin and mucous membranes and may be present in the form of ointments, creams, milks, ointments, powders, soaked 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 of formula (I), or one of its salts, 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 in particular:
  • pH regulating agents osmotic pressure modifying agents; emulsifying 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;
  • antiseborrhoeic or antiacne agents such as S-carboxymethylcysteine, S-benzylcysteamine, their salts or their 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;
  • 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);
  • anti-psoriatic agents such as anthralin and its derivatives; - eicosa-5,8,11,14-tetraynoic and eicosa-5,8,11-triynoic acids, their esters and amides;
  • retinoids that is to say ligands of the RAR or RXR receptors, natural or synthetic;
  • VDR receptors ligands of VDR receptors
  • - corticosteroids or estrogens ligands of VDR receptors
  • ⁇ -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; 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 ).
  • medicaments known to interfere with the immune system for example cyclosporin, FK 506, glucocorticoids, monoclonal antibodies, soluble receptors, cytokines or of growth .
  • the compounds of formula (I) are especially synthesized as described in application WO00 / 44709.
  • the edema is induced by a single application of 20 ⁇ l of TPA dissolved in acetone at 0.01%.
  • the test compound is diluted in the TPA solution and applied at a concentration of 0.1%, 0.3% and 1%.
  • VdB ⁇ -methasone valerate
  • Apratastat has a dose-dependent anti-inflammatory effect, and reduces TPA-induced ear edema by 25% (NS) (at 0.1%), 47% (**) (at 0.3%) and 49% (**) (at 1%).

Landscapes

  • Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Dermatology (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Rheumatology (AREA)
  • Pain & Pain Management (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicinal Preparation (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP07731755A 2006-03-20 2007-03-16 Verwendung von (3s)-n-hydroxy-4-({4-¦(4-hydroxy-2-butynyl)oxy]phenyl}sulfonyl)-2,2-dimethyl-3-thiomorpholin-carboxamid bzw. (s)-n-hydroxy-4-(4-but-2-ynyloxy-benzolsulfonyl) -2,2-dimethyl-thiomorpholin-3-carboxamid zur behandlung entzündlicher hautkrankheiten Withdrawn EP1998779A2 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0602429A FR2898497B1 (fr) 2006-03-20 2006-03-20 Utilisation de l'apratastat ou du (s)-n-hydroxy-4-(4-but-2- ynyloxy-benzenesulfonyl)-2,2-dimethyl-thiomorpholine-3-carbo xamide dans le traitement de pathologies inflammatoires cutanees
PCT/FR2007/050939 WO2007107663A2 (fr) 2006-03-20 2007-03-16 Utilisation du (3s)-n-hydroxy-4-({4-[(4-hydroxy-2-butynyl)oxy]phényl}sulfonyl)-2,2-diméthyl-3-thiomorpholine carboxamide ou du (s)-n-hydroxy-4-(4-but-2-ynyloxy-benzenesulfonyl) -2,2-dimethyl-thiomorpholine -3-carboxamide dans le traitement de pathologies inflammatoires cutanées

Publications (1)

Publication Number Publication Date
EP1998779A2 true EP1998779A2 (de) 2008-12-10

Family

ID=37057052

Family Applications (1)

Application Number Title Priority Date Filing Date
EP07731755A Withdrawn EP1998779A2 (de) 2006-03-20 2007-03-16 Verwendung von (3s)-n-hydroxy-4-({4-¦(4-hydroxy-2-butynyl)oxy]phenyl}sulfonyl)-2,2-dimethyl-3-thiomorpholin-carboxamid bzw. (s)-n-hydroxy-4-(4-but-2-ynyloxy-benzolsulfonyl) -2,2-dimethyl-thiomorpholin-3-carboxamid zur behandlung entzündlicher hautkrankheiten

Country Status (5)

Country Link
US (1) US20090137569A1 (de)
EP (1) EP1998779A2 (de)
CA (1) CA2645327A1 (de)
FR (1) FR2898497B1 (de)
WO (1) WO2007107663A2 (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012005229A1 (ja) 2010-07-08 2012-01-12 科研製薬株式会社 Ｎ－ヒドロキシホルムアミド誘導体およびそれを含有する医薬
GB2483499A (en) 2010-09-10 2012-03-14 S3 Res & Dev Ltd Diagnostics and Analysis of a Set Top Box
FR3046933B1 (fr) * 2016-01-25 2018-03-02 Galderma Research & Development Inhibiteurs nlrp3 pour le traitement des pathologies cutanees inflammatoires

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5594106A (en) * 1993-08-23 1997-01-14 Immunex Corporation Inhibitors of TNF-α secretion
AR035313A1 (es) * 1999-01-27 2004-05-12 Wyeth Corp Inhibidores de tace acetilenicos de acido hidroxamico de sulfonamida a base de alfa-aminoacidos, composiciones farmaceuticas y el uso de los mismos para la manufactura de medicamentos.
US6225311B1 (en) * 1999-01-27 2001-05-01 American Cyanamid Company Acetylenic α-amino acid-based sulfonamide hydroxamic acid tace inhibitors
AU2003284001A1 (en) * 2002-10-07 2004-05-04 Bristol-Myers Squibb Company Triazolone and triazolethione derivatives
GT200500139A (es) * 2004-06-08 2005-07-25 Metodo para la preparacion de acidos hidroxamicos

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2007107663A2 *

Also Published As

Publication number Publication date
CA2645327A1 (fr) 2007-09-27
WO2007107663A2 (fr) 2007-09-27
WO2007107663A3 (fr) 2007-11-22
FR2898497A1 (fr) 2007-09-21
FR2898497B1 (fr) 2008-05-16
US20090137569A1 (en) 2009-05-28

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