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WO2002036592A1 - Remedes aux maladies causees par l'acide arachidonique - Google Patents

Remedes aux maladies causees par l'acide arachidonique Download PDF

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Publication number
WO2002036592A1
WO2002036592A1 PCT/JP2001/009575 JP0109575W WO0236592A1 WO 2002036592 A1 WO2002036592 A1 WO 2002036592A1 JP 0109575 W JP0109575 W JP 0109575W WO 0236592 A1 WO0236592 A1 WO 0236592A1
Authority
WO
WIPO (PCT)
Prior art keywords
arachidonic acid
acid
skin diseases
cell carcinoma
skin
Prior art date
Application number
PCT/JP2001/009575
Other languages
English (en)
Japanese (ja)
Inventor
Takamasa Watanabe
Masako Uchida
Masazumi Terashima
Original Assignee
Sumitomo Pharmaceuticals Company, Limited
Japan Energy Corporation
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 Sumitomo Pharmaceuticals Company, Limited, Japan Energy Corporation filed Critical Sumitomo Pharmaceuticals Company, Limited
Priority to AU2002212695A priority Critical patent/AU2002212695A1/en
Publication of WO2002036592A1 publication Critical patent/WO2002036592A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • 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
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/4745—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines
    • 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
    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • 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
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Definitions

  • the present invention relates to a therapeutic agent for skin diseases. More specifically, the present invention relates to a preventive or therapeutic agent for a skin disease caused by an increase in arachidonic acid metabolism, such as psoriasis, ultraviolet dermatitis, hypertrophy, basal cell carcinoma or stabular cell carcinoma.
  • arachidonic acid metabolism such as psoriasis, ultraviolet dermatitis, hypertrophy, basal cell carcinoma or stabular cell carcinoma.
  • Prostaglandins (PGs) and leucos (LTs) produced by acid metabolic pathways are involved in the regulation of physiological functions such as gastric acid secretion, platelet aggregation, and various smooth muscle contractions, and are fatty acids that cause tissue inflammation.
  • Communicator (mediator) PG and LT are important for the maintenance of homeostasis in the body, but overproduction of some dermatological diseases is considered to be the main cause of the disease.
  • Psoriasis is a chronic disease that shows benign abnormal proliferation of epidermal cells and infiltration of polymorphonuclear leukocytes into the epidermis, and is closely related to abnormalities of arachidonic acid metabolites for the following reasons (1) to (4). It is considered a disease.
  • (1) PG, arachidonic acid and 12-HETE increase in psoriatic rash
  • LTB 4 Leukotriene 5,12-dihydroxy form
  • Representative examples of skin diseases caused by abnormal arachidonic acid metabolism include the following diseases.
  • Mastocytosis This is a condition in which histamine and other substances are released from mast cells grown on the skin, causing flushing of the skin and junctional measles. Although these symptoms are considered to be mainly due to histamine, antihistamines are used.However, histamine-resistant cases in which PG synthesis inhibitors are significantly improved are seen (Main, RA et al. Br. . J.
  • Sunlight dermatitis It is thought that inflammatory mediators such as PG cause vasodilation by medium wavelength ultraviolet light.
  • Basal cell carcinoma or stab cell carcinoma (all skin cancers): PG is increased, and it has been suggested that PG is involved in the growth of the tumor (Vanderveen, ⁇ ., . ⁇ ⁇ et al.
  • Antiviral activity Antiviral activity in a herpesvirus (Tomai. MA. Et al. Antiviral Res. 28, 253-264 (1995)) infection system has been reported.
  • Cytokine 9883-845 (1997)), which is not found in imiquimod but found only in R848, is due to the skin inflammation-inducing action of TNF_a; (Kondo, S et al. Eur Combined with J. Immunol. 27, 1713-8 (1997), it suggests that R848 may induce skin inflammation.
  • An object of the present invention is to provide a novel skin disease therapeutic agent for treating and Z or preventing a skin disease caused by enhanced arachidonic acid metabolism, that is, a skin disease caused by increased production of PG, LT and the like. .
  • the present inventors have already found the inhibitory effect of imiquimod on arachidonic acid-induced mouse ear edema, and have filed a patent application for the invention of a therapeutic agent for skin diseases such as psoriasis (Japanese Patent Application Laid-Open No. 2000-247884, supra).
  • Rimi848 an analog of imiquimod, exhibits an extremely strong and persistent inhibitory action on arachidonic acid-induced mouse ear edema, and thus completed the present invention. That is, the gist of the present invention is represented by the following [1] to [6].
  • R848 (4-amino-2-ethoxymethyl- ⁇ , ⁇ -dimethyl-1 ⁇ -imidazo [4,5-c] quinolin-1-ethanol, hereinafter abbreviated as R848) or an acid addition salt or solvate thereof
  • R848 4-amino-2-ethoxymethyl- ⁇ , ⁇ -dimethyl-1 ⁇ -imidazo [4,5-c] quinolin-1-ethanol, hereinafter abbreviated as R848) or an acid addition salt or solvate thereof
  • skin disease caused by an increase in arachidonic acid metabolism means a skin disease caused by an abnormal increase in arachidonic acid and its metabolites constituting an arachidonic acid metabolic pathway (arachidonic acid cascade).
  • Typical disease names include psoriasis, UV dermatitis, mastocytosis, basal cell carcinoma or barbed cell carcinoma.
  • Arachidonic acid metabolites are: (1) Prostaglandins produced by cyclooxygenase enzymes: PGE (prostaglandin E), PGF, PGI, TXA (thrompoxane A), etc., (2) lipoxygenase enzymes Leukotrienes produced by: LTB4, LTC, LTD, LTE, etc., and (3) 12-HETE etc., and inflammatory skin diseases resulting from abnormal increase of these mediators are described in the present invention. Applicable.
  • the skin disease according to the present invention is caused by a virus or bacterial infection, skin inflammation due to burn injury or trauma, skin disease associated with collagen disease (autoimmune disease such as systemic lupus erythematosus, scleroderma), or a heterogeneous immune reaction. Does not include allergic skin diseases (junction, contact dermatitis, atopic dermatitis, etc.).
  • autoimmune disease such as systemic lupus erythematosus, scleroderma
  • a heterogeneous immune reaction Does not include allergic skin diseases (junction, contact dermatitis, atopic dermatitis, etc.).
  • the active ingredient of the present invention can be easily synthesized according to a known method.
  • a method described in W098 / 17279 may be used.
  • the acid of the acid addition salt of R848 is not particularly limited as long as it is a pharmacologically acceptable acid, and may be a solvate such as a hydrate.
  • Acid addition salts include inorganic acids (eg, hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, and nitric acid), acetic acid, oxalic acid, tartaric acid, succinic acid, malic acid, ascorbic acid, benzoic acid, tannic acid, pamoic acid It is formed with organic acids such as arginic acid, polydalminic acid, naphthylene sulfonic acid, naphthalenedisulfonic acid and polygalacturonic acid. Hydrochloric acid, sulfuric acid, acetic acid, oxalic acid, ascorbic acid and the like are suitable acid addition salts.
  • R848 and its salts can take various formulation forms (eg, liquids, solids, capsules, etc.).
  • Dosage forms for oral administration include, for example, tablets, capsules, pills, granules, powders, solutions, suspensions, and the like.
  • Dosage forms for parenteral administration include, for example, injections Aqueous or oily agents, ointments, creams, lotions, aerosols, suppositories, patches and the like can be mentioned.
  • the active ingredient can be incorporated with excipients and used in solutions, powders, powders, tablets, troches or capsules.
  • Pharmaceutically compatible binding agents, and Z or adjuvant materials can be included as part of the composition.
  • Tablets, pills, capsules and troches and the like can contain any of the following ingredients or compounds which are similar in nature: binder such as microcrystalline cellulose, gum tragacanth or gelatin; starch or lactate.
  • Excipients such as glucose; dispersing agents such as alginic acid, rimogel or corn starch; magnesium stearate or Are lubricants such as Sterotes; lubricants such as colloidal silicon dioxide; sweeteners such as sucrose or saccharin; or, such as peppermint, methyl salicylate or orange flavor. Flavoring agent.
  • the dosage unit form When the dosage unit form is forceps, it may contain, in addition to materials of the above type, a liquid carrier such as a fatty oil.
  • dosage unit forms can contain various other materials which modify the physical form of the dosage unit, for example, coatings of sugar, shellac or enteric agents.
  • R848 and a pharmaceutically acceptable salt can be administered as an ingredient such as an elixir, suspension, syrup, wafer, or gum.
  • a syrup may contain, in addition to the active ingredients, sucrose as a sweetening agent and certain preservatives, dyes and colorings and flavors.
  • R8488 can also be prepared as a sustained release formulation including implants and microcapsule administration systems.
  • a biodegradable and biocompatible polymer such as ethylene vinyl acetate, polyanhydride, polyglycolic acid, collagen, silicon, polyorthoester and polylactic acid can be used. Methods for preparing such formulations will be apparent to those skilled in the art, and the materials are also commercially available.
  • a ribosome suspension can be prepared by a method known to those skilled in the art using an appropriate lipid (eg, stearoyl phosphatidylethanolamine, stearate roll) as a carrier.
  • Solutions or suspensions used for parenteral, intradermal, subcutaneous or topical applications containing R848 as an active ingredient can include the following ingredients.
  • Sterile diluents such as water for injection, saline solution, fixed oils, fixed oils, polyethylene glycols, glycerin, propylene dalycol or other synthetic solvents; fungicides such as benzyl alcohol or methyl paraben; ascorbic acid or sulfite Antioxidants such as sodium hydrogen; chelating agents such as ethylenediaminetetraacetic acid; acetate, citrate Or buffers such as phosphate and agents for adjusting tonicity such as sodium chloride or dextrose.
  • Parenteral preparations may be enclosed in ampoules, disposable syringes or multiple dose vials made of glass or plastic.
  • Injectables can be prepared in a conventional manner, for example, by dissolving the compound in an appropriate solvent (eg, sterilized water, buffer, physiological saline, etc.), and then sterilizing by filtering through a filter or the like. Then, it can be prepared by filling in a sterile container.
  • the preferred carriers are saline or phosphate buffered saline (PBS).
  • PBS phosphate buffered saline
  • an external preparation is one of particularly suitable dosage forms.
  • R 848 is imiquimod with approximate chemical structure, 1- (2-methylpropyl)-1H-imidazo [4,5-c] quinoline-4- at least 20 times more water-soluble than quinoline-4-amine (Water solubility at pH 2.5, 5.5, and 7: 1000 ⁇ /] 111 or more). Due to this property, the medicament of the present invention is not only easy to formulate, but also has a low transferability of the active ingredient to the central and other tissues. The effect on the affected area is durable. As described above, the R848-containing preparation of the present invention has particularly excellent properties as an external preparation.
  • the form of the external preparation is not particularly limited, and may be in the form of cream, paste, jelly, gel, emulsion, liquid, etc.
  • any pharmaceutically acceptable base may be used, and conventionally known bases such as ointments, liniments, lotions and the like can be used.
  • polyvinyl alcohol sodium polyacrylate, methoxyethylene-polymers such as maleic anhydride copolymer, poly
  • inorganic fillers such as kaolin, bentonite, zinc oxide, and titanium oxide; viscosity regulators; antioxidants; PH regulators; humectants such as glycerin and propylene glycol may be added. .
  • external bases In the case of external bases (ointments, creams, etc.), generally 1 to 100 mg, preferably 3 to 300 mg, of R8488 or a salt thereof is contained as an active ingredient per 1 g of plaster. Can be.
  • the dosage form and dosage of the medicament of the present invention are not particularly limited, and may be any method that can be used by a person skilled in the art as appropriate.
  • oral administration in the case of oral administration, it can be administered in the form of inhalants or capsules, tablets, granules, etc.
  • inhalants or capsules, tablets, granules, etc. in the range of about 1 to about 100 mg / day for adults for adults It is preferably administered in the range of about 10 to about 50 mg in one or several doses.
  • parenteral administration it can be used in the form of subcutaneous or intravenous injections, drops, or ointments in an aqueous suspension.
  • the dose varies depending on the patient's condition, age, weight, etc., and the dose used will be appropriately large enough to effectively treat the target disease.
  • a range of 100 mg, preferably about 3 to about 100 mg, can be administered in one or several divided doses.
  • topical transdermal preparations solutions, oily ointments, hydrophilic ointments or creams
  • the amount used depends on the type and condition of the disease.
  • the amount of external preparation should be 0.1 to 100 g, more preferably 1 to 10 g per day, applied once or at appropriate times to the affected area. Good. Industrial applicability
  • various skin diseases caused by abnormal arachidonic acid metabolism can be treated safely and effectively.
  • arachidonic acid metabolism such as psoriasis, ultraviolet dermatitis, mastocytosis, basal cell tumor, and barbed cell carcinoma
  • BALB / c mice female, 6 weeks old were purchased from Charles River Japan (Kanagawa, Japan) and preliminarily reared and used until 8 weeks old.
  • R848 (2 mg / mK 20 mg / ml) showed a significant inhibitory effect on arachidonic acid-induced intradermal reaction even after 4 hours from application. This result indicates that the preparation containing R848 is effective as a therapeutic or prophylactic agent for skin diseases caused by increased arachidonic acid metabolism.
  • Table 2 Water solubility of R848 and imiquimod in the acidic to neutral range

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

Abstract

L'invention concerne des médicaments servant à prévenir et/ou à traiter des maladies de la peau causées par l'acide arachidonique, et contenant comme principe actif 4-amino-2-éthoxyméthyl-α,α-diméthyl-1H-imidazo[4,5-c]quinoline-1-éthanol:R848 ou son sel ou solvat d'ddition acide. L'utilisation de ces médicaments permet de traiter de manière sûre et efficace diverses maladies de la peau causées par le métabolisme accéléré de l'acide ararchidonique (psoriasis, dermatite réagissant aux ultra-violets, mastocytome, basilome, carcinome cellulaire squameux, etc.).
PCT/JP2001/009575 2000-11-06 2001-10-31 Remedes aux maladies causees par l'acide arachidonique WO2002036592A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2002212695A AU2002212695A1 (en) 2000-11-06 2001-10-31 Remedies for arachidonic acid-induced skin diseases

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2000-337359 2000-11-06
JP2000337359A JP2002145777A (ja) 2000-11-06 2000-11-06 アラキドン酸誘発皮膚疾患治療剤

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WO2002036592A1 true WO2002036592A1 (fr) 2002-05-10

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