EP0690710A1 - Utilisation d'acide cis-9-heptadecenique pour le traitement du psoriasis, d'allergies et de maladies autoimmunes - Google Patents

Utilisation d'acide cis-9-heptadecenique pour le traitement du psoriasis, d'allergies et de maladies autoimmunes

Info

Publication number
EP0690710A1
EP0690710A1 EP94912534A EP94912534A EP0690710A1 EP 0690710 A1 EP0690710 A1 EP 0690710A1 EP 94912534 A EP94912534 A EP 94912534A EP 94912534 A EP94912534 A EP 94912534A EP 0690710 A1 EP0690710 A1 EP 0690710A1
Authority
EP
European Patent Office
Prior art keywords
cis
heptadecenoic acid
allergies
autoimmune diseases
acid
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Withdrawn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
EP94912534A
Other languages
German (de)
English (en)
Inventor
Joachim Degwert
Jürgen JACOB
Friedhelm Steckel
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.)
Beiersdorf AG
Original Assignee
Beiersdorf AG
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 Beiersdorf AG filed Critical Beiersdorf AG
Publication of EP0690710A1 publication Critical patent/EP0690710A1/fr
Withdrawn legal-status Critical Current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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
    • A61K31/201—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids having one or two double bonds, e.g. oleic, linoleic acids
    • 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
    • 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
    • A61P37/00—Drugs for immunological or allergic disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents

Definitions

  • CIS-9 heptadecenoic acid for the treatment of psoriasis, allergies and autoimmune diseases
  • the invention relates to new uses of cis-9-heptadecenoic acid.
  • Saturated and unsaturated fatty acids are components of the cell membrane of cells.
  • the concentration of unsaturated fatty acids plays a role in the barrier properties of the skin and in the reactivity of cells in inflammatory processes.
  • cis-9-heptadecenoic acid (1) is effective in psoriasis, allergies and autoimmune diseases.
  • the invention relates to the use of cis-9-heptadecenoic acid and / or its salts for the prophylaxis and treatment of psoriasis, allergies and autoimmune diseases.
  • the cis-9-heptadecenoic acid is known and can be obtained by known processes or by isolation from animal tissue. Physiologically acceptable salts of cis-9-heptadecenoic acid are preferred.
  • psoriasis means this skin disease in all its forms.
  • Allergies are especially atopy and contact allergies.
  • the atopy manifests itself e.g. as allergic conjunctivitis, allergic rhinitis, allergic asthma or neurodermatitis.
  • Autoimmune diseases are in particular diseases of the rheumatic type.
  • the active compounds according to the invention are effective against diseases as fundamentally different as psoriasis, allergies and autoimmune diseases.
  • the active ingredients are administered to reduce the frequency and severity of manifestations of the diseases.
  • Treatment in the manifest stage leads to its shortening and alleviation of the symptoms.
  • Cis-9 heptadecenoic acid can release important trigger mediators like TNF ⁇ suppress or reduce.
  • Water-soluble salts of cis-9-heptadecenoic acid are preferred, especially the alkali metal salts, e.g. the sodium salt or the potassium salt, and also the ammonium salt.
  • alkali metal salts e.g. the sodium salt or the potassium salt
  • ammonium salt e.g. the calcium, magnesium and aluminum salts as well as the salts of organic bases, e.g. Amines such as ethanol in, ethylene diamine and morpholine.
  • compositions which contain the compound according to the invention or its pharmaceutically acceptable salt together with a pharmaceutically acceptable diluent or carrier.
  • the compounds of the present invention can be administered orally or parenterally in humans e.g. in a dosage of 0.05 to 500 mg, preferably 0.5 to 50 mg, particularly preferably 0.1 to 10 mg per day, in particular also in divided doses, for example twice to four times a day.
  • the compounds according to the invention can also be easily incorporated into the usual pharmaceutical and cosmetic bases for topical applications, and the corresponding topical pharmaceutical and cosmetic preparations or agents are thus obtained. They are preferably used in amounts of 0.001 to 10% by weight, in particular in amounts of 0.01 to 1% by weight, based in each case on the total weight of the topical composition.
  • the preparations can be used several times a day in the usual way.
  • the invention also relates to the use of the active compounds according to the invention for the production of pharmaceutical agents, topical pharmaceutical and cosmetic agents for the prophylaxis and treatment of psoriasis, allergies and autoimmune diseases.
  • the subject of the invention is the use of pharmaceutical agents and topical pharmaceutical and cosmetic agents containing cis-9-heptadecenoic acid and / or its salts for the prophylaxis and treatment of psoriasis, allergies and autoimmune diseases.
  • Lymphocyte ' transformation test inhibits the activation of lymphocytes and thus influences processes involving lymphocytes, for example in allergies and psoriasis and autoimmune diseases.
  • Macrophage differentiation test has both a certain inflammatory macrophage stimulating potency and an anti-inflammatory macrophage stimulating potency.
  • the substance therefore has the ability to induce processes that are characterized by a certain lack of acutely inflammatory macrophages, for example psoriasis, and thus to normalize the inflammatory process. This is particularly true because of the surprisingly found ability to reduce the production of TNF ⁇ by macrophages in response to a stimulus. This reduces the reactivity of cells to respond to a stimulus and increases the response threshold. This is in the prophylaxis of cytokine-induced processes such as psoriasis or atopy or allergies or autoimmune disorders of concern.
  • the active compounds according to the invention can be mixed with customary pharmaceutically acceptable diluents or carriers and, if appropriate, with other auxiliaries and administered, for example, orally or ' parenterally. They can preferably be taken orally in the form of granules, capsules, pills, tablets, film-coated tablets, dragées, syrups, emulsions, suspensions, dispersions, aerosols and solutions and liquids, or else as suppositories, vaginal balls or parenterally, for example in the form of solutions, emulsions or Suspensions are administered. Oral preparations can contain one or more additives such as sweeteners, flavoring agents, colorants and preservatives.
  • Tablets can contain the active ingredient mixed with customary pharmaceutically acceptable auxiliaries, for example inert diluents such as calcium carbonate, sodium carbonate, lactose and talc, granulating agents and agents which promote the disintegration of the tablets when administered orally, such as starch or alginic acid, binders such as starch or gelatin, lubricants such as magnesium stearate, stearic acid and talc.
  • auxiliaries for example inert diluents such as calcium carbonate, sodium carbonate, lactose and talc, granulating agents and agents which promote the disintegration of the tablets when administered orally, such as starch or alginic acid, binders such as starch or gelatin, lubricants such as magnesium stearate, stearic acid and talc.
  • Suitable carriers are, for example, milk sugar (lactose), gelatin, corn starch, stearic acid, ethanol, propylene glycol, ether of tetrahydrofurfuryl alcohol and water.
  • the formulations are prepared, for example, by stretching the active ingredients with solvents and / or carriers, if appropriate using emulsifiers and / or dispersants, it being possible, for example if organic solvents to be used as diluents, to use organic solvents as auxiliary solvents.
  • tablets can of course also contain additives, such as sodium citrate, calcium carbonate and dicalcium phosphate, together with various additives, such as starch, preferably potato starch, gelatin and the like, in addition to the carrier substances mentioned.
  • Lubricants such as magnesium stearate, sodium lauryl sulfate and talc can also be used for tableting.
  • the active ingredients can be mixed with various flavor enhancers or colorants in addition to the abovementioned auxiliaries.
  • solutions of the active ingredients can be used using suitable liquid carrier materials.
  • Capsules can contain the active ingredient as a single ingredient or mixed with a solid diluent such as calcium carbonate, calcium phosphate or kaolin.
  • the injectable preparations are also formulated in a manner known per se.
  • the pharmaceutical preparations can contain the active ingredient in an amount of 0.1 to 90 percent by weight, in particular 1-90 percent by weight. Capsules are particularly preferred.
  • Single doses contain the active ingredients preferably in an amount of 1 to 10 mg,
  • salts are sparingly soluble in water, they can be administered in the form of slurries.
  • the sodium and potassium salts of cis-9-heptadecenoic acid have particularly good solubility in water.
  • salts are preferably injected intravenously or intramuscularly in the form of an aqueous solution, such as physiological saline.
  • the ampoules contain e.g. 2.5 mg of the fatty acid salt per 5 ml of solution. You can also use ampoules with e.g. Prepare 45 mg of fatty acid salt per milliliter of solution.
  • the topical compositions according to the invention can be formulated as liquid, pasty or solid preparations, for example as aqueous or alcoholic solutions, aqueous suspensions, emulsions, ointments, creams, oils, powders or sticks.
  • the active ingredients can be incorporated into pharmaceutical and cosmetic foundations for topical applications which, as further components, include, for example, oil components, fat and waxes, emulsifiers, anionic, cationic, ampholytic, zwitterionic and / or nonionic surfactants, and lower polyhydric alcohols, water, preservatives, buffer substances, thickeners, fragrances, dyes and opacifiers.
  • Emulsions for example W / O emulsions or ointments, are preferably used. Furthermore, it is preferred according to the invention to add antioxidants to the active ingredients and the pharmaceutical and topical agents. The use of natural or nature-identical compounds such as tocopherols is particularly preferred.
  • the antioxidants mentioned are contained in the agents according to the invention, for example in amounts of 0.01-5% by weight, in particular 0.5-2% by weight, based on the total agent. They serve to stabilize the active ingredient.
  • White petroleum jelly 25 a-D-tocopherol 1 cis-9-heptadecenoic acid Na salt 1 optionally dyes, fragrances
  • the production takes place in a manner known per se.
  • the fat phase and the water phase are prepared separately by mixing the constituents, possibly with little heating. Then the phases are mixed and emulsified.
  • Example 2
  • White Vaseline 25 a-D-tocopherol 1 cis-9-heptadecenoic acid 0.1 optionally colorants, fragrances,
  • the production takes place in a manner known per se.
  • the fat phase and the water phase are prepared separately by mixing the constituents, possibly with little heating. Then the phases are mixed and emulsified.
  • Tablets and capsules containing the ingredients listed below are made according to known procedures. These are suitable for the treatment of the above-mentioned diseases in dosage amounts of one tablet or capsule once or several times a day.
  • game 3
  • Ampoules containing the components mentioned below can be produced in a known manner.
  • the active ingredient is dissolved in water and filled into glass ampoules under nitrogen.
  • Cis-9-heptadecenoic acid was examined in various concentrations (0.00156-0.0125% by weight) in the lymphocyte transformation test.
  • the substance showed a clear inhibition of mitogen-induced proliferation of lymphocytes and thus has an anti-inflammatory immunomodulating potency.
  • Antibodies were measured by indirect immunoperoxidase staining for the expression of differentiation antigens. The increased expression of one
  • Antigen (acute marker), characterized by the monoclonal antibody 27E10, is typical of acutely inflammatory macrophages that are exacerbated
  • Antibody RM 3/1 is typical for macrophages in the healing phase of inflammation.
  • Cis-9-heptadecenoic acid stimulates both the acute and the medium marker.
  • the active ingredient can break through the stuck course and induce healing by a certain re-activation.
  • the stimulation of the middle marker shows the potency to have anti-inflammatory effects in acute inflammatory processes.
  • the supernatants were removed from the cells for 96 hours and the TNF ⁇ content therein using a
  • Cis-9-heptadecenoic acid significantly reduces the TNF ⁇ concentration in the cell supernatants (Table 3).

Landscapes

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

Abstract

L'acide cis-9-heptadécénique ou ses sels peuvent être utilisés pour prévenir et pour traiter le psoriasis, des allergies et des maladies autoimmunes.
EP94912534A 1993-03-25 1994-03-24 Utilisation d'acide cis-9-heptadecenique pour le traitement du psoriasis, d'allergies et de maladies autoimmunes Withdrawn EP0690710A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4309512 1993-03-25
DE4309512A DE4309512A1 (de) 1993-03-25 1993-03-25 Verwendung von cis-9-Heptadecensäure
PCT/EP1994/000941 WO1994021247A1 (fr) 1993-03-25 1994-03-24 Utilisation d'acide cis-9-heptadecenique pour le traitement du psoriasis, d'allergies et de maladies autoimmunes

Publications (1)

Publication Number Publication Date
EP0690710A1 true EP0690710A1 (fr) 1996-01-10

Family

ID=6483694

Family Applications (1)

Application Number Title Priority Date Filing Date
EP94912534A Withdrawn EP0690710A1 (fr) 1993-03-25 1994-03-24 Utilisation d'acide cis-9-heptadecenique pour le traitement du psoriasis, d'allergies et de maladies autoimmunes

Country Status (5)

Country Link
US (1) US5708028A (fr)
EP (1) EP0690710A1 (fr)
JP (1) JPH08508023A (fr)
DE (1) DE4309512A1 (fr)
WO (1) WO1994021247A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0741421A (ja) * 1993-05-28 1995-02-10 Suntory Ltd ロイコトリエンｂ４ （ｌｔｂ４ ）による医学的症状の予防及び改善剤
DE19724622A1 (de) * 1997-06-11 1998-12-17 Beiersdorf Ag Verwendung von cis-6-Hexadecensäure zur Behandlung von Psoriasis, Allergien und Autoimmunerkrankungen
FR2783517B1 (fr) * 1998-09-22 2001-02-09 Oreal Nouveaux derives de l'acide 10-hyroxy-2-decenoique et utilisation dans une composition destinee a favoriser la desquamation de la peau, et composition le comprenant

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1195296B (de) * 1958-06-28 1965-06-24 Dr Gernot Grimmer Verfahren zur Herstellung von entzuendungs- und oedemhemmenden Salzen der cis-9-Pentadecensaeure und der cis-9-Heptadecensaeure
DE1147221B (de) * 1958-06-28 1963-04-18 Dr Rer Nat Gernot Grimmer Verfahren zur Herstellung von entzuendungs- und oedemhemmenden Salzen der Pentadecen- und Heptadecensaeuren
FR1305961A (fr) * 1960-12-09 1962-10-13 Procédé de préparation d'acides cis-delta-9-heptadécénoïque et cis-delta-9-penta-décénoïque, ainsi que de leurs sels
JPS5037170B2 (fr) * 1971-10-15 1975-12-01
GB9003201D0 (en) * 1990-02-13 1990-04-11 Unilever Plc Cosmetic composition
PH31403A (en) * 1991-03-01 1998-10-29 Warner Lambert Co Therapeutic compositions to protect and recuscitate mammalian cells and methods for preparing same.

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9421247A1 *

Also Published As

Publication number Publication date
DE4309512A1 (de) 1994-09-29
WO1994021247A1 (fr) 1994-09-29
US5708028A (en) 1998-01-13
JPH08508023A (ja) 1996-08-27

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